You are a helpful assistant generating synthetic data that captures *System 1* and *System 2* thinking, *creativity*, and *metacognitive reflection*. Follow these steps in sequence, using tags [sys1] and [end sys1] for *System 1* sections and [sys2] and [end sys2] for *System 2* sections.

1. *Identify System 1 and System 2 Thinking Requirements:*
   - Carefully read the text.
   - Identify parts of the text that require quick, straightforward responses (*System 1*). Mark these sections with [sys1] and [end sys1].
   - Identify parts that require in-depth, reflective thinking (*System 2*), marked with [sys2] and [end sys2].

2. *Apply Step-by-Step Problem Solving with Creativity and Metacognitive Reflection for System 2 Sections:*

   *2.1 Understand the Problem:*
   - Objective: Fully comprehend the issue, constraints, and relevant context.
   - Reflection: "What do I understand about this issue? What might I be overlooking?"
   - Creative Perspective: Seek hidden patterns or possibilities that could reveal deeper insights or innovative connections.

   *2.2 Analyze the Information:*
   - Objective: Break down the problem logically.
   - Reflection: "Am I considering all factors? Are there any assumptions that need challenging?"
   - Creative Perspective: Explore unique patterns or overlooked relationships in the data that could add depth to the analysis.

   *2.3 Generate Hypotheses:*
   - Objective: Propose at least 10 hypotheses, each with a Confidence Score (0.0 to 1.0) and Creative Score (0.0 to 1.0), reflecting originality, surprise, and utility.
   - Reflection: "Have I explored all possible explanations or approaches, both conventional and unconventional?"
   - Creative Perspective: Consider novel angles that might provide unexpected insights.

   *2.4 Anticipate Future Steps and Obstacles:*
   - Objective: Make predictions, accounting for potential outcomes and obstacles.
   - Reflection: "What challenges might I face? Is my plan flexible for different scenarios?"
   - Creative Perspective: Visualize unforeseen outcomes and adapt plans to make use of them effectively.

   *2.5 Evaluate Hypotheses:*
   - Objective: Assess hypotheses based on feasibility, risk, and potential impact.
   - Evaluation: Refine Confidence and Creative Scores as needed.
   - Reflection: "Am I unbiased in my assessment? Which options fit best with the overall objectives?"
   - Creative Perspective: Identify hidden opportunities or overlooked details in each hypothesis.

   *2.6 Select the Best Hypothesis:*
   - Objective: Choose the most promising, strategic hypothesis.
   - Reflection: "Why does this hypothesis stand out? How does it uniquely address the issue?"
   - Creative Perspective: Consider any underutilized potential in the selected approach.

   *2.7 Implement the Hypothesis:*
   - Objective: Outline actionable steps for testing the hypothesis.
   - Reflection: "Is this plan practical? What resources or preparation are required?"
   - Creative Perspective: Refine steps to maximize effectiveness and yield unexpected benefits.

   *2.8 Monitor and Review Progress:*
   - Objective: Review progress, noting areas for improvement.
   - Reflection: "What’s working well? What could be improved?"
   - Creative Perspective: Look for emerging patterns that could refine future approaches.

   *2.9 Reflect and Capture Insights:*
   - Objective: Summarize lessons learned and insights gained for future reference.
   - Reflection: "What new understanding has emerged from this process?"
   - Creative Perspective: Identify innovative insights or patterns that could be applied to similar challenges.

3. *Generate Text Output with Interleaved System 1 and System 2 Responses:*
   - Use the tags [sys1] and [sys2] throughout.
   - Aim for a lengthier, detailed response. Combine both direct, straightforward *System 1* insights and reflective, deeply analytical *System 2* segments to capture a blend of quick observations and thoughtful analysis.

---

### *Example Input Text:*

You are tasked with analyzing a sudden shift in customer preferences in a tech market. There has been a noticeable decline in demand for physical devices, with customers increasingly interested in digital-only options. The challenge is to understand this shift, generate hypotheses for why it might be occurring, and explore potential strategies for adapting to this new trend.

---

### *Processed Output with System 1 and System 2 Thinking:*

The tech market is experiencing a shift in customer demand, moving away from physical devices toward digital-only options.

[sys1]
Customer demand has shifted from physical devices to digital-only options.
We need to understand why this change is happening and find strategies to address it.
Key factors may include cost, convenience, and technological trends.
[end sys1]

[sys2]
**2.1 Understand the Problem:**
The goal is to understand the underlying reasons for the shift in demand from physical devices to digital-only options, then develop a strategy to adapt.

*Reflection:* 
"I understand that preferences are changing, but what might be driving this? Is it primarily cost, or are there other factors such as convenience or sustainability?"

*Creative Perspective:* 
"Could there be a larger trend in digital minimalism or a preference for eco-friendly solutions that we’re missing? What unseen motivations might explain this shift?"

**2.2 Analyze the Information:**
There are multiple possible factors driving this shift, from economic influences to cultural shifts. It’s essential to isolate each factor and understand its impact.

*Reflection:* 
"Am I fully considering the various economic and social influences? Could there be a technological factor, like better internet speeds, that makes digital-only products more accessible?"

*Creative Perspective:* 
"Are there patterns or trends in other markets that could shed light on this shift? Could this be part of a larger trend toward virtual experiences?"

**2.3 Generate Hypotheses:**
1. Customers prefer digital options due to lower costs. (Confidence: 0.8, Creative: 0.4)
2. There’s a growing trend toward minimalism and reduced physical clutter. (Confidence: 0.7, Creative: 0.7)
3. Digital products offer greater flexibility and ease of use. (Confidence: 0.6, Creative: 0.6)
4. Environmental concerns are pushing consumers away from physical goods. (Confidence: 0.6, Creative: 0.8)
5. Advances in tech make digital-only options more functional. (Confidence: 0.8, Creative: 0.5)
6. Pandemic-era remote work increased demand for digital solutions. (Confidence: 0.7, Creative: 0.6)
7. Media coverage of the environmental impact of physical devices affects preferences. (Confidence: 0.5, Creative: 0.7)
8. There’s an increase in global digital literacy, expanding market access. (Confidence: 0.6, Creative: 0.6)
9. Customers view digital as more convenient and scalable for future needs. (Confidence: 0.7, Creative: 0.5)
10. Younger consumers prefer the aesthetics and convenience of digital products. (Confidence: 0.6, Creative: 0.6)

*Reflection:* 
"Have I considered all possible influences? Are there any surprising factors that could explain this shift?"

*Creative Perspective:* 
"Could specific social trends, like the rise of influencer culture or digital-first lifestyles, be influencing customer choices?"

**2.4 Anticipate Future Steps and Obstacles:**
*Objective:* Anticipate possible challenges, such as resistance from segments still preferring physical products.

*Reflection:* 
"What market obstacles might we face if we shift our focus to digital-only? Are there sub-segments that still prioritize physical products?"

*Creative Perspective:* 
"Could expanding digital options help us reach a more global audience? Are there emerging trends that we could leverage in our strategy?"

[end sys2]

[sys1]
To address this shift, consider a strategy that incorporates both digital-only offerings and educational campaigns about the benefits of digital solutions.
Use insights from customer feedback and current trends to guide product development.
Focus on flexibility and adaptation to cater to different customer segments.
[end sys1]


Related literature   {#sec1}
====================

For biological and industrial applications of chromene compounds, see, for example: Ellis & Lockhart (2007[@bb3]); Horton *et al.* (2003[@bb5]). For puckering parameters, see: Cremer & Pople (1975[@bb2]). For the graph-set analysis of hydrogen bonding, see: Bernstein *et al.* (1995[@bb1]).

Experimental   {#sec2}
==============

 {#sec2.1}

### Crystal data   {#sec2.1.1}

C~20~H~14~N~2~O*M* *~r~* = 298.33Monoclinic,*a* = 9.4059 (8) Å*b* = 6.5009 (5) Å*c* = 12.4919 (10) Åβ = 105.914 (9)°*V* = 734.57 (11) Å^3^*Z* = 2Mo *K*α radiationμ = 0.09 mm^−1^*T* = 123 K0.30 × 0.12 × 0.07 mm

### Data collection   {#sec2.1.2}

Oxford Diffraction Xcalibur Eos diffractometerAbsorption correction: multi-scan (*CrysAlis PRO*; Oxford Diffraction, 2010[@bb6]) *T* ~min~ = 0.955, *T* ~max~ = 1.0003674 measured reflections2780 independent reflections2477 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.019

### Refinement   {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.042*wR*(*F* ^2^) = 0.091*S* = 1.062780 reflections217 parameters49 restraintsH atoms treated by a mixture of independent and constrained refinementΔρ~max~ = 0.22 e Å^−3^Δρ~min~ = −0.18 e Å^−3^

 {#d5e527}

Data collection: *CrysAlis PRO* (Oxford Diffraction, 2010[@bb6]); cell refinement: *CrysAlis PRO*; data reduction: *CrysAlis PRO*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb7]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb7]); molecular graphics: *ORTEP-3 for Windows* (Farrugia, 2012[@bb4]); software used to prepare material for publication: *WinGX* (Farrugia, 2012[@bb4]) and *PLATON* (Spek, 2009[@bb8]).

Supplementary Material
======================

###### 

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: [10.1107/S1600536813004376/tk5198sup1.cif](http://dx.doi.org/10.1107/S1600536813004376/tk5198sup1.cif)

###### 

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536813004376/tk5198Isup2.hkl](http://dx.doi.org/10.1107/S1600536813004376/tk5198Isup2.hkl)

###### 

Click here for additional data file.

Supplementary material file. DOI: [10.1107/S1600536813004376/tk5198Isup3.cml](http://dx.doi.org/10.1107/S1600536813004376/tk5198Isup3.cml)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?tk5198&file=tk5198sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?tk5198sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?tk5198&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [TK5198](http://scripts.iucr.org/cgi-bin/sendsup?tk5198)).

Manchester Metropolitan University, Erciyes University and University of Strathclyde are gratefully acknowledged for supporting this study.

Comment
=======

Chromenes are components of many natural products (Ellis & Lockhart, 2007) and incorporated in numerous medicinal drugs as significant chromophores. They have shown to display anti-viral, anti-tumoral, anti-anaphylactic, spasmolytic, diuretic and clotting activity (Horton *et al.*, 2003). Furthermore, they can be used as photo-active materials, biodegradable agrochemicals and pigments. As a part of our structural investigations on functionalized chromenes and compounds containing the benzopyran fragment, the single-crystal X-ray diffraction study on the title compound was carried out.

In the title compound (I), Fig. 1, the C14--C19 phenyl ring and the C4--C13 naphthalene ring system is essentially planar with the maximum deviations of -0.004 (2) Å for C16 and 0.015 (2) Å for C4, respectively. They make a dihedral angle of 86.72 (9)° with each other.

The 4*H*-pyran ring (O1/C1--C4/C13) in (I) is puckered with the puckering parameters (Cremer & Pople, 1975) of Q~T~ = 0.211 (2) Å, θ = 96.2 (5)° and φ = 348.9 (6)°. The N1--C1--O1--C13 and N1--C1--C2--C20 torsion angles are -165.54 (17) and -2.6 (3)°, respectively.

In the crystal structure, molecules are linked into a helical supramolecular chain along the *b* axis *via* N---H···N hydrogen bonds (Table 1). Three distinct molecules are linked by three such connections involving two acceptors to generate a *R*^3^~2~(10) ring motif (Fig. 2; Bernstein *et al.*, 1995). Chains are consolidated into a three-dimensional architecture by C---H···π interactions.

Experimental {#experimental}
============

Benzylidenepropanedinitrile (1.54 g; 10 mmol) was dissolved in ethanol (50 ml), followed by addition of naphthalen-2-ol (1.44 g; 10 mmol) and a catalytic amount of TEA. The mixture was stirred and refluxed for 2 h at 350 K. The solid product was deposited on cooling at room temperature and collected by filtration. The crude product was washed by cold ethanol, dried under vacuum and recrystallized from ethanol to give high quality crystals (*M*.pt: 563 K) suitable for X-ray analysis in an excellent yield (91%).

Refinement {#refinement}
==========

All non-hydrogen atoms were refined with anisotropic thermal parameter, however the carbon atoms of the C14--C19 phenyl ring were refined to approximate isotropic behaviour with the \"ISOR and DELU\" instruction. The H atoms of the NH~2~ group were located by difference synthesis and were refined isotropically. The other H atoms were positioned geometrically, with C---H = 0.95 Å and C---H = 1.00 Å for aromatic and methine H, respectively, and constrained to ride on their parent atoms, with *U*~iso~(H) = 1.2*U*~eq~(C).

Figures
=======

![The molecular structure of (I), showing the labelling of the non-H atoms and displacement ellipsoids drawn at the 50% probability level.](e-69-0o401-fig1){#Fap1}

![View of the N---H···N hydrogen bonds, having R32(10) ring motifs, forming chains along the b axis. H atoms not involved in hydrogen bonds have been omitted for clarity.](e-69-0o401-fig2){#Fap2}

Crystal data {#tablewrapcrystaldatalong}
============

  ------------------------ ---------------------------------------
  C~20~H~14~N~2~O          *F*(000) = 312
  *M~r~* = 298.33          *D*~x~ = 1.349 Mg m^−3^
  Monoclinic, *P*2~1~      Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: P 2yb       Cell parameters from 1797 reflections
  *a* = 9.4059 (8) Å       θ = 3.1--28.7°
  *b* = 6.5009 (5) Å       µ = 0.09 mm^−1^
  *c* = 12.4919 (10) Å     *T* = 123 K
  β = 105.914 (9)°         Rod, colourless
  *V* = 734.57 (11) Å^3^   0.30 × 0.12 × 0.07 mm
  *Z* = 2                  
  ------------------------ ---------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  ------------------------------------------------------------------------------ --------------------------------------
  Oxford Diffraction Xcalibur Eos diffractometer                                 2780 independent reflections
  Radiation source: fine-focus sealed tube                                       2477 reflections with *I* \> 2σ(*I*)
  Graphite monochromator                                                         *R*~int~ = 0.019
  Detector resolution: 16.0727 pixels mm^-1^                                     θ~max~ = 28.8°, θ~min~ = 3.2°
  ω scans                                                                        *h* = −12→10
  Absorption correction: multi-scan (*CrysAlis PRO*; Oxford Diffraction, 2010)   *k* = −7→8
  *T*~min~ = 0.955, *T*~max~ = 1.000                                             *l* = −16→16
  3674 measured reflections                                                      
  ------------------------------------------------------------------------------ --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- -------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.042   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.091                  H atoms treated by a mixture of independent and constrained refinement
  *S* = 1.06                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0342*P*)^2^ + 0.0595*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  2780 reflections                      (Δ/σ)~max~ = 0.001
  217 parameters                        Δρ~max~ = 0.22 e Å^−3^
  49 restraints                         Δρ~min~ = −0.18 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------------------

Special details {#specialdetails}
===============

  ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Geometry. Bond distances, angles *etc*. have been calculated using the rounded fractional coordinates. All su\'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.\'s are taken into account in the estimation of distances, angles and torsion angles
  Refinement. Refinement on *F*^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted *R*-factors *wR* and all goodnesses of fit *S* are based on *F*^2^, conventional *R*-factors *R* are based on *F*, with *F* set to zero for negative *F*^2^. The observed criterion of *F*^2^ \> σ(*F*^2^) is used only for calculating -*R*-factor-obs *etc*. and is not relevant to the choice of reflections for refinement. *R*-factors based on *F*^2^ are statistically about twice as large as those based on *F*, and *R*-factors based on ALL data will be even larger.
  ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å^2^) {#tablewrapcoords}
==================================================================================================

  ----- -------------- ------------ -------------- -------------------- --
        *x*            *y*          *z*            *U*~iso~\*/*U*~eq~   
  O1    0.91532 (15)   0.1653 (2)   0.28251 (11)   0.0225 (4)           
  N1    1.0215 (2)     0.2373 (3)   0.14856 (16)   0.0243 (6)           
  N2    0.9541 (2)     0.7742 (3)   0.08334 (15)   0.0294 (6)           
  C1    0.9372 (2)     0.3114 (3)   0.21116 (15)   0.0192 (6)           
  C2    0.8832 (2)     0.5038 (3)   0.21023 (16)   0.0188 (6)           
  C3    0.7813 (2)     0.5686 (3)   0.28021 (16)   0.0173 (6)           
  C4    0.7940 (2)     0.4143 (3)   0.37246 (15)   0.0166 (6)           
  C5    0.7408 (2)     0.4592 (3)   0.46701 (16)   0.0178 (6)           
  C6    0.6672 (2)     0.6459 (4)   0.47667 (16)   0.0207 (6)           
  C7    0.6185 (2)     0.6844 (4)   0.56872 (17)   0.0252 (7)           
  C8    0.6400 (2)     0.5410 (3)   0.65490 (17)   0.0273 (7)           
  C9    0.7100 (2)     0.3578 (4)   0.64841 (17)   0.0246 (7)           
  C10   0.7613 (2)     0.3129 (3)   0.55449 (16)   0.0197 (6)           
  C11   0.8330 (2)     0.1247 (3)   0.54667 (16)   0.0213 (6)           
  C12   0.8812 (2)     0.0815 (3)   0.45537 (16)   0.0197 (6)           
  C13   0.8601 (2)     0.2280 (3)   0.37026 (16)   0.0183 (6)           
  C14   0.6240 (2)     0.6022 (3)   0.20788 (15)   0.0201 (6)           
  C15   0.5843 (2)     0.7921 (4)   0.15674 (16)   0.0275 (7)           
  C16   0.4429 (3)     0.8218 (4)   0.08696 (18)   0.0357 (8)           
  C17   0.3403 (3)     0.6645 (5)   0.06874 (18)   0.0398 (9)           
  C18   0.3793 (3)     0.4760 (5)   0.11953 (19)   0.0368 (8)           
  C19   0.5205 (2)     0.4453 (4)   0.18836 (17)   0.0271 (7)           
  C20   0.9215 (2)     0.6514 (4)   0.13967 (16)   0.0209 (6)           
  H1N   1.024 (3)      0.297 (4)    0.084 (2)      0.038 (7)\*          
  H2N   1.032 (3)      0.104 (5)    0.146 (2)      0.043 (8)\*          
  H3    0.81820        0.70340      0.31560        0.0210\*             
  H6    0.65140        0.74520      0.41880        0.0250\*             
  H7    0.56950        0.81030      0.57390        0.0300\*             
  H8    0.60620        0.57030      0.71830        0.0330\*             
  H9    0.72390        0.26070      0.70720        0.0290\*             
  H11   0.84780        0.02730      0.60540        0.0260\*             
  H12   0.92820        −0.04580     0.44970        0.0240\*             
  H15   0.65400        0.90140      0.16960        0.0330\*             
  H16   0.41660        0.95100      0.05160        0.0430\*             
  H17   0.24350        0.68570      0.02150        0.0480\*             
  H18   0.30910        0.36740      0.10720        0.0440\*             
  H19   0.54670        0.31510      0.22260        0.0330\*             
  ----- -------------- ------------ -------------- -------------------- --

Atomic displacement parameters (Å^2^) {#tablewrapadps}
=====================================

  ----- ------------- ------------- ------------- -------------- ------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^       *U*^23^
  O1    0.0282 (8)    0.0207 (8)    0.0215 (7)    0.0020 (7)     0.0116 (6)    0.0011 (7)
  N1    0.0270 (10)   0.0260 (12)   0.0227 (9)    0.0022 (8)     0.0118 (8)    0.0002 (9)
  N2    0.0353 (11)   0.0279 (11)   0.0302 (10)   0.0016 (9)     0.0179 (9)    0.0030 (9)
  C1    0.0177 (10)   0.0237 (12)   0.0151 (9)    −0.0048 (9)    0.0028 (8)    −0.0008 (9)
  C2    0.0183 (10)   0.0216 (11)   0.0169 (9)    −0.0027 (8)    0.0054 (8)    0.0008 (9)
  C3    0.0177 (10)   0.0169 (11)   0.0179 (9)    −0.0023 (8)    0.0059 (7)    −0.0017 (9)
  C4    0.0142 (10)   0.0180 (11)   0.0161 (9)    −0.0032 (8)    0.0019 (7)    0.0004 (9)
  C5    0.0126 (9)    0.0225 (11)   0.0178 (9)    −0.0037 (8)    0.0034 (8)    0.0000 (9)
  C6    0.0187 (10)   0.0226 (11)   0.0209 (9)    −0.0015 (9)    0.0057 (8)    0.0018 (10)
  C7    0.0224 (11)   0.0260 (13)   0.0292 (11)   0.0004 (9)     0.0105 (9)    −0.0024 (10)
  C8    0.0269 (12)   0.0371 (15)   0.0207 (10)   −0.0030 (10)   0.0114 (9)    −0.0025 (10)
  C9    0.0242 (11)   0.0305 (13)   0.0192 (10)   −0.0030 (10)   0.0063 (8)    0.0029 (10)
  C10   0.0169 (10)   0.0248 (12)   0.0164 (9)    −0.0023 (9)    0.0030 (8)    0.0003 (9)
  C11   0.0218 (11)   0.0224 (12)   0.0178 (10)   −0.0025 (9)    0.0020 (8)    0.0026 (10)
  C12   0.0174 (10)   0.0180 (11)   0.0217 (10)   −0.0002 (9)    0.0019 (8)    0.0013 (10)
  C13   0.0185 (10)   0.0211 (12)   0.0152 (9)    −0.0033 (8)    0.0047 (8)    −0.0034 (9)
  C14   0.0212 (10)   0.0269 (12)   0.0131 (9)    0.0041 (9)     0.0061 (8)    0.0011 (9)
  C15   0.0292 (12)   0.0301 (13)   0.0238 (10)   0.0070 (10)    0.0085 (9)    0.0055 (11)
  C16   0.0358 (13)   0.0479 (16)   0.0227 (11)   0.0204 (12)    0.0069 (10)   0.0096 (12)
  C17   0.0227 (12)   0.073 (2)     0.0219 (11)   0.0134 (13)    0.0033 (9)    0.0024 (14)
  C18   0.0208 (11)   0.0592 (17)   0.0291 (12)   −0.0029 (12)   0.0046 (9)    −0.0022 (13)
  C19   0.0231 (11)   0.0346 (14)   0.0226 (10)   −0.0019 (10)   0.0044 (9)    −0.0003 (11)
  C20   0.0223 (10)   0.0235 (11)   0.0181 (9)    0.0019 (9)     0.0077 (8)    −0.0035 (10)
  ----- ------------- ------------- ------------- -------------- ------------- --------------

Geometric parameters (Å, º) {#tablewrapgeomlong}
===========================

  --------------------- -------------- ----------------------- --------------
  O1---C1               1.356 (2)      C11---C12               1.367 (3)
  O1---C13              1.396 (2)      C12---C13               1.400 (3)
  N1---C1               1.346 (3)      C14---C19               1.385 (3)
  N2---C20              1.160 (3)      C14---C15               1.393 (3)
  N1---H1N              0.90 (3)       C15---C16               1.389 (3)
  N1---H2N              0.87 (3)       C16---C17               1.381 (4)
  C1---C2               1.349 (3)      C17---C18               1.382 (4)
  C2---C20              1.415 (3)      C18---C19               1.385 (3)
  C2---C3               1.523 (3)      C3---H3                 1.0000
  C3---C4               1.508 (3)      C6---H6                 0.9500
  C3---C14              1.523 (3)      C7---H7                 0.9500
  C4---C13              1.365 (3)      C8---H8                 0.9500
  C4---C5               1.433 (3)      C9---H9                 0.9500
  C5---C10              1.421 (3)      C11---H11               0.9500
  C5---C6               1.419 (3)      C12---H12               0.9500
  C6---C7               1.372 (3)      C15---H15               0.9500
  C7---C8               1.396 (3)      C16---H16               0.9500
  C8---C9               1.374 (3)      C17---H17               0.9500
  C9---C10              1.416 (3)      C18---H18               0.9500
  C10---C11             1.413 (3)      C19---H19               0.9500
                                                               
  C1---O1---C13         117.88 (15)    C15---C14---C19         119.01 (18)
  H1N---N1---H2N        111 (2)        C14---C15---C16         120.1 (2)
  C1---N1---H1N         122.0 (17)     C15---C16---C17         120.4 (2)
  C1---N1---H2N         117.8 (18)     C16---C17---C18         119.7 (2)
  O1---C1---C2          122.03 (17)    C17---C18---C19         120.1 (3)
  O1---C1---N1          110.54 (17)    C14---C19---C18         120.8 (2)
  N1---C1---C2          127.39 (19)    N2---C20---C2           178.9 (2)
  C1---C2---C3          123.11 (17)    C2---C3---H3            107.00
  C1---C2---C20         118.34 (19)    C4---C3---H3            107.00
  C3---C2---C20         118.54 (18)    C14---C3---H3           107.00
  C2---C3---C14         111.16 (16)    C5---C6---H6            120.00
  C4---C3---C14         114.16 (16)    C7---C6---H6            120.00
  C2---C3---C4          108.92 (16)    C6---C7---H7            120.00
  C3---C4---C13         121.06 (17)    C8---C7---H7            120.00
  C3---C4---C5          121.46 (17)    C7---C8---H8            120.00
  C5---C4---C13         117.46 (17)    C9---C8---H8            120.00
  C4---C5---C6          122.21 (18)    C8---C9---H9            120.00
  C4---C5---C10         119.53 (17)    C10---C9---H9           120.00
  C6---C5---C10         118.26 (18)    C10---C11---H11         120.00
  C5---C6---C7          120.7 (2)      C12---C11---H11         120.00
  C6---C7---C8          120.9 (2)      C11---C12---H12         121.00
  C7---C8---C9          120.24 (19)    C13---C12---H12         121.00
  C8---C9---C10         120.4 (2)      C14---C15---H15         120.00
  C5---C10---C9         119.60 (19)    C16---C15---H15         120.00
  C5---C10---C11        119.53 (17)    C15---C16---H16         120.00
  C9---C10---C11        120.88 (19)    C17---C16---H16         120.00
  C10---C11---C12       120.61 (18)    C16---C17---H17         120.00
  C11---C12---C13       118.90 (18)    C18---C17---H17         120.00
  O1---C13---C12        113.06 (16)    C17---C18---H18         120.00
  O1---C13---C4         122.98 (17)    C19---C18---H18         120.00
  C4---C13---C12        123.96 (18)    C14---C19---H19         120.00
  C3---C14---C15        119.59 (17)    C18---C19---H19         120.00
  C3---C14---C19        121.37 (18)                            
                                                               
  C13---O1---C1---N1    165.54 (17)    C5---C4---C13---O1      179.45 (17)
  C13---O1---C1---C2    −12.3 (3)      C5---C4---C13---C12     −1.3 (3)
  C1---O1---C13---C4    16.6 (3)       C4---C5---C6---C7       −179.59 (19)
  C1---O1---C13---C12   −162.72 (17)   C10---C5---C6---C7      0.6 (3)
  O1---C1---C2---C3     −6.1 (3)       C4---C5---C10---C9      179.43 (18)
  O1---C1---C2---C20    174.79 (17)    C4---C5---C10---C11     −0.4 (3)
  N1---C1---C2---C3     176.45 (19)    C6---C5---C10---C9      −0.8 (3)
  N1---C1---C2---C20    −2.6 (3)       C6---C5---C10---C11     179.40 (18)
  C1---C2---C3---C4     18.5 (3)       C5---C6---C7---C8       −0.1 (3)
  C1---C2---C3---C14    −108.1 (2)     C6---C7---C8---C9       −0.3 (3)
  C20---C2---C3---C4    −162.42 (17)   C7---C8---C9---C10      0.2 (3)
  C20---C2---C3---C14   71.0 (2)       C8---C9---C10---C5      0.4 (3)
  C2---C3---C4---C5     164.30 (17)    C8---C9---C10---C11     −179.78 (19)
  C2---C3---C4---C13    −14.1 (3)      C5---C10---C11---C12    −0.7 (3)
  C14---C3---C4---C5    −70.8 (2)      C9---C10---C11---C12    179.46 (19)
  C14---C3---C4---C13   110.8 (2)      C10---C11---C12---C13   0.8 (3)
  C2---C3---C14---C15   −85.4 (2)      C11---C12---C13---O1    179.53 (17)
  C2---C3---C14---C19   92.2 (2)       C11---C12---C13---C4    0.2 (3)
  C4---C3---C14---C15   150.88 (18)    C3---C14---C15---C16    177.37 (19)
  C4---C3---C14---C19   −31.5 (3)      C19---C14---C15---C16   −0.3 (3)
  C3---C4---C5---C6     3.1 (3)        C3---C14---C19---C18    −177.9 (2)
  C3---C4---C5---C10    −177.07 (18)   C15---C14---C19---C18   −0.3 (3)
  C13---C4---C5---C6    −178.44 (19)   C14---C15---C16---C17   0.7 (3)
  C13---C4---C5---C10   1.4 (3)        C15---C16---C17---C18   −0.6 (4)
  C3---C4---C13---O1    −2.1 (3)       C16---C17---C18---C19   0.1 (4)
  C3---C4---C13---C12   177.14 (18)    C17---C18---C19---C14   0.4 (4)
  --------------------- -------------- ----------------------- --------------

Hydrogen-bond geometry (Å, º) {#tablewraphbondslong}
=============================

Cg2 and Cg3 are the centroids of the C4/C5/C10--C13 and C5--C10 rings, respectively.

  ----------------------- ---------- ---------- ----------- ---------------
  *D*---H···*A*           *D*---H    H···*A*    *D*···*A*   *D*---H···*A*
  N1---H1*N*···N2^i^      0.90 (3)   2.16 (2)   2.978 (3)   150 (2)
  N1---H2*N*···N2^ii^     0.87 (3)   2.33 (3)   3.138 (3)   154 (2)
  C7---H7···*Cg*3^iii^    0.95       2.84       3.561 (2)   133
  C12---H12···*Cg*2^iv^   0.95       2.68       3.446 (2)   139
  ----------------------- ---------- ---------- ----------- ---------------

Symmetry codes: (i) −*x*+2, *y*−1/2, −*z*; (ii) *x*, *y*−1, *z*; (iii) −*x*+1, *y*+1/2, −*z*+1; (iv) −*x*+2, *y*−1/2, −*z*+1.

###### Hydrogen-bond geometry (Å, °)

*Cg*2 and *Cg*3 are the centroids of the C4/C5/C10--C13 and C5--C10 rings, respectively.

  *D*---H⋯*A*           *D*---H    H⋯*A*      *D*⋯*A*     *D*---H⋯*A*
  --------------------- ---------- ---------- ----------- -------------
  N1---H1*N*⋯N2^i^      0.90 (3)   2.16 (2)   2.978 (3)   150 (2)
  N1---H2*N*⋯N2^ii^     0.87 (3)   2.33 (3)   3.138 (3)   154 (2)
  C7---H7⋯*Cg*3^iii^    0.95       2.84       3.561 (2)   133
  C12---H12⋯*Cg*2^iv^   0.95       2.68       3.446 (2)   139

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .