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

For the biological and pharmacological properties of pyridine-based heterocycles, see: Aida *et al.* ( 2009[@bb1]); Ceylan & Gezegen (2008[@bb2]); Cundy *et al.* ( 1997[@bb4]); El-borai *et al.* ( 2012[@bb5]); Gezegen *et al.* ( 2010[@bb7]); Girgis *et al.* ( 2007[@bb8]); Hatanaka *et al.* ( 2005[@bb9]); Khidre *et al.* ( 2011[@bb10]); Laine-Cessac *et al.* ( 1997[@bb11]); Menegatti *et al.* ( 2006[@bb12]); Musiol *et al.* ( 2007[@bb13]); Rajanarendar *et al.* ( 2012[@bb14]).  For ring conformation analysis, see: Cremer & Pople (1975[@bb3]). 

Experimental   {#sec2}
==============

 {#sec2.1}

### Crystal data   {#sec2.1.1}

C~23~H~22~BrNO*M* *~r~* = 408.32Monoclinic,*a* = 10.409 (5) Å*b* = 10.054 (5) Å*c* = 18.428 (5) Åβ = 94.850 (5)°*V* = 1921.6 (14) Å^3^*Z* = 4Mo *K*α radiationμ = 2.15 mm^−1^*T* = 296 K0.58 × 0.42 × 0.26 mm

### Data collection   {#sec2.1.2}

Stoe IPDS 2 diffractometerAbsorption correction: integration (*X-RED32*; Stoe & Cie, 2002[@bb17]) *T* ~min~ = 0.355, *T* ~max~ = 0.57228207 measured reflections3986 independent reflections3083 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.178

### Refinement   {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.060*wR*(*F* ^2^) = 0.119*S* = 1.123986 reflections235 parametersH-atom parameters constrainedΔρ~max~ = 0.67 e Å^−3^Δρ~min~ = −0.42 e Å^−3^

 {#d5e401}

Data collection: *X-AREA* (Stoe & Cie, 2002[@bb17]); cell refinement: *X-AREA*; data reduction: *X-RED32* (Stoe & Cie, 2002[@bb17]); program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb15]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb15]); molecular graphics: *ORTEP-3 for Windows* (Farrugia, 2012[@bb6]); software used to prepare material for publication: *WinGX* (Farrugia, 2012[@bb6]) and *PLATON* (Spek, 2009[@bb16]). 

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

###### 

Click here for additional data file. 

Crystal structure: contains datablock(s) global, I. DOI: [10.1107/S1600536813013913/rz5059sup1.cif](http://dx.doi.org/10.1107/S1600536813013913/rz5059sup1.cif)

###### 

Click here for additional data file. 

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536813013913/rz5059Isup2.hkl](http://dx.doi.org/10.1107/S1600536813013913/rz5059Isup2.hkl)

###### 

Click here for additional data file. 

Supplementary material file.  DOI: [10.1107/S1600536813013913/rz5059Isup3.cml](http://dx.doi.org/10.1107/S1600536813013913/rz5059Isup3.cml)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?rz5059&file=rz5059sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?rz5059sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?rz5059&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [RZ5059](http://scripts.iucr.org/cgi-bin/sendsup?rz5059)). 

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). 

Comment
=======

Pyridine based heterocycles are found in structure of many natural and biologically important compounds (Aida *et al.*,  2009; Laine-Cessac *et al.*,  1997; Musiol *et al.*,  2007).  Also they are known to exhibit numerous biological and pharmacological properties such as antimicrobial (El-borai *et al.*,  2012), antifungal (Khidre *et al.*,  2011), antiviral (Cundy *et al.*,  1997), anticancer (Rajanarendar *et al.*,  2012), antioxidant (Hatanaka *et al.*,  2005), anti-inflammatory (Girgis *et al.*,  2007) and analgesic (Menegatti *et al.*,  2006) activities.  In this paper we report synthesis of 2-(4-bromophenyl)-4-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5*H*-cyclohepta\[*b*\]pyridine with high yield and its crystal structure. 

The molecular structure of the title compound (I) is shown in Fig.  1.  The cycloheptane ring (C4--C10) of (I) adopts a chair conformation \[the puckering parameters (Cremer & Pople, 1975) are Q(2) = 0.422 (4) Å and φ(2) = 311.3 (5)°\].  The pyridine ring (N1/C1--C5) makes dihedral angles of 58.63 (15) and 8.27 (16)° with the two benzene rings (C11--C16 and C18--C23), respectively, which have a dihedral angle of 56.68 (17)° between them. 

The crystal packing is stabilized by C---Br···π interactions (C21---Br1···*Cg*1^i^: Br···A = 3.813 (2) Å, D---H···A = 126.25 (10)°; C21---Br1···*Cg*2^ii^: Br···A = 3.839 (2) Å, D---H···A = 138.31 (10)°; *Cg*1 and *Cg*2 are the centroids of the N1/C1--C5 and C11--C16 rings, respectively; symmetry codes: (i) x, 1/2-y, 1/2 + z; (ii) -x, -y, 1-z).  Fig.  2 represents the molecular packing viewed down the *b* axis. 

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

2-(4-Bromophenyl)-4-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5*H*-cyclohepta\[*b*\]pyridine was synthesized from the 1,5-diketone derivative (Ceylan & Gezegen, 2008) according to the literature method (Gezegen *et al.*,  2010).  To a solution of 2-\[3-(4-bromophenyl)-1-(4-methoxyphenyl)-3-oxopropyl\]cycloheptanone (1 mmol) in EtOH-AcOH (20 ml 1:1 *v*/*v*) was added NH~4~Ac (4 mmol) and the mixture refluxed for 6 h. After completion of the reaction, the solvent was removed under vacuum and the residue was extracted with CH~2~Cl~2~ (2 × 25 ml).  The organic layer was dried over Na~2~SO~4~ and evaporated.  The crude product was purified by column chromatography (on a silica gel) eluting with hexane/CHCl~3~ (3:1 *v*/*v*).  The obtained brown product was crystallized from EtOH to give pure 2-(4-bromophenyl)-4-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5*H*-cyclohepta\[*b*\]pyridine in 95% yield; m. p. = 396--398 K.

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

H-atoms were positioned geometrically and refined using a riding model with C---H = 0.93--0.97 Å, and with *U*~iso~(H) = 1.2 or 1.5*U*~eq~(C).  Crystals of the title compound were of limited quality.  Even though it was possible to select a specimen suitable for X-ray diffraction experiment, the data obtained were rather poor and the value of R~int~ remained high (17.8%). 

Figures
=======

![ The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.](e-69-0o956-fig1){#Fap1}

![ Packing diagram of the title compound viewed down the b axis.](e-69-0o956-fig2){#Fap2}

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

  ------------------------- ---------------------------------------
  C~23~H~22~BrNO            *F*(000) = 840
  *M~r~* = 408.32           *D*~x~ = 1.411 Mg m^−3^
  Monoclinic, *P*2~1~/*c*   Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2ybc      Cell parameters from 3507 reflections
  *a* = 10.409 (5) Å        θ = 2.0--29.7°
  *b* = 10.054 (5) Å        µ = 2.15 mm^−1^
  *c* = 18.428 (5) Å        *T* = 296 K
  β = 94.850 (5)°           Prism, yellow
  *V* = 1921.6 (14) Å^3^    0.58 × 0.42 × 0.26 mm
  *Z* = 4                   
  ------------------------- ---------------------------------------

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

  ------------------------------------------------------------------ --------------------------------------
  Stoe IPDS 2 diffractometer                                         3986 independent reflections
  Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus   3083 reflections with *I* \> 2σ(*I*)
  Plane graphite monochromator                                       *R*~int~ = 0.178
  Detector resolution: 6.67 pixels mm^-1^                            θ~max~ = 26.5°, θ~min~ = 2.0°
  ω scans                                                            *h* = −13→13
  Absorption correction: integration (*X-RED32*; Stoe & Cie, 2002)   *k* = −12→12
  *T*~min~ = 0.355, *T*~max~ = 0.572                                 *l* = −23→23
  28207 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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.060   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.119                  H-atom parameters constrained
  *S* = 1.12                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0476*P*)^2^ + 0.6943*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  3986 reflections                      (Δ/σ)~max~ \< 0.001
  235 parameters                        Δρ~max~ = 0.67 e Å^−3^
  0 restraints                          Δρ~min~ = −0.42 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~   
  Br1    0.22100 (4)   0.14765 (5)   0.68332 (2)    0.0767 (1)           
  O1     −0.3941 (2)   0.0596 (2)    0.06337 (14)   0.0741 (9)           
  N1     0.3068 (2)    0.0105 (3)    0.32719 (14)   0.0564 (9)           
  C1     0.1937 (3)    0.0478 (3)    0.35239 (16)   0.0532 (10)          
  C2     0.0825 (3)    0.0575 (3)    0.30651 (17)   0.0562 (10)          
  C3     0.0829 (3)    0.0282 (3)    0.23272 (17)   0.0544 (10)          
  C4     0.2004 (3)    −0.0098 (3)   0.20640 (17)   0.0553 (10)          
  C5     0.3082 (3)    −0.0176 (3)   0.25619 (17)   0.0568 (10)          
  C6     0.4390 (3)    −0.0579 (4)   0.2335 (2)     0.0700 (12)          
  C7     0.4441 (4)    −0.1991 (4)   0.2031 (2)     0.0798 (16)          
  C8     0.3898 (4)    −0.2128 (5)   0.1245 (2)     0.0865 (17)          
  C9     0.2484 (4)    −0.1809 (4)   0.1093 (2)     0.0839 (16)          
  C10    0.2126 (4)    −0.0375 (4)   0.12674 (19)   0.0721 (14)          
  C11    −0.0402 (3)   0.0400 (3)    0.18588 (16)   0.0551 (10)          
  C12    −0.1082 (3)   0.1580 (3)    0.18180 (18)   0.0595 (11)          
  C13    −0.2265 (3)   0.1698 (3)    0.14134 (18)   0.0601 (11)          
  C14    −0.2783 (3)   0.0606 (3)    0.10434 (17)   0.0586 (11)          
  C15    −0.2119 (4)   −0.0577 (4)   0.1079 (2)     0.0728 (12)          
  C16    −0.0948 (4)   −0.0675 (4)   0.1480 (2)     0.0691 (11)          
  C17    −0.4694 (4)   0.1773 (4)    0.0621 (2)     0.0760 (14)          
  C18    0.1993 (3)    0.0751 (3)    0.43212 (16)   0.0505 (9)           
  C19    0.3097 (3)    0.0476 (4)    0.47628 (18)   0.0647 (11)          
  C20    0.3172 (3)    0.0689 (4)    0.55055 (19)   0.0641 (11)          
  C21    0.2123 (3)    0.1207 (3)    0.58153 (17)   0.0562 (10)          
  C22    0.1016 (3)    0.1529 (4)    0.53894 (18)   0.0658 (11)          
  C23    0.0957 (3)    0.1291 (3)    0.46491 (18)   0.0624 (11)          
  H2     0.00620       0.08400       0.32510        0.0670\*             
  H6A    0.50170       −0.05060      0.27530        0.0830\*             
  H6B    0.46390       0.00400       0.19690        0.0830\*             
  H7A    0.53320       −0.22860      0.20700        0.0960\*             
  H7B    0.39660       −0.25760      0.23300        0.0960\*             
  H8A    0.43830       −0.15480      0.09480        0.1040\*             
  H8B    0.40390       −0.30340      0.10890        0.1040\*             
  H9A    0.19910       −0.24060      0.13770        0.1000\*             
  H9B    0.22330       −0.19800      0.05820        0.1000\*             
  H10A   0.27760       0.02140       0.10980        0.0870\*             
  H10B   0.13120       −0.01610      0.09960        0.0870\*             
  H12    −0.07370      0.23180       0.20690        0.0710\*             
  H13    −0.27030      0.25050       0.13930        0.0720\*             
  H15    −0.24640      −0.13170      0.08300        0.0870\*             
  H16    −0.05130      −0.14840      0.14970        0.0830\*             
  H17A   −0.54790      0.16370       0.03180        0.1140\*             
  H17B   −0.42180      0.24920       0.04290        0.1140\*             
  H17C   −0.48930      0.19860       0.11060        0.1140\*             
  H19    0.38120       0.01360       0.45550        0.0780\*             
  H20    0.39230       0.04840       0.57930        0.0770\*             
  H22    0.03170       0.19020       0.55980        0.0790\*             
  H23    0.02040       0.14980       0.43630        0.0750\*             
  ------ ------------- ------------- -------------- -------------------- --

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

  ----- ------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  Br1   0.0721 (2)    0.1010 (3)    0.0569 (2)    0.0059 (2)     0.0055 (2)     −0.0121 (2)
  O1    0.0727 (15)   0.0659 (15)   0.0804 (16)   0.0092 (12)    −0.0131 (12)   −0.0115 (12)
  N1    0.0601 (16)   0.0502 (14)   0.0594 (15)   0.0013 (12)    0.0077 (12)    −0.0005 (12)
  C1    0.0608 (18)   0.0430 (16)   0.0564 (16)   0.0004 (14)    0.0080 (14)    0.0016 (13)
  C2    0.0578 (17)   0.0502 (18)   0.0613 (17)   0.0005 (14)    0.0096 (14)    −0.0026 (14)
  C3    0.0634 (18)   0.0427 (16)   0.0570 (17)   −0.0029 (14)   0.0039 (14)    0.0017 (13)
  C4    0.0655 (19)   0.0487 (17)   0.0528 (16)   −0.0003 (14)   0.0115 (14)    0.0005 (13)
  C5    0.0653 (18)   0.0504 (18)   0.0557 (17)   0.0000 (15)    0.0119 (14)    −0.0012 (14)
  C6    0.065 (2)     0.081 (2)     0.065 (2)     0.0042 (19)    0.0118 (16)    −0.0063 (18)
  C7    0.083 (3)     0.082 (3)     0.076 (2)     0.019 (2)      0.017 (2)      −0.005 (2)
  C8    0.094 (3)     0.085 (3)     0.083 (3)     0.008 (2)      0.022 (2)      −0.024 (2)
  C9    0.089 (3)     0.090 (3)     0.074 (2)     −0.008 (2)     0.015 (2)      −0.023 (2)
  C10   0.073 (2)     0.085 (3)     0.0592 (19)   −0.001 (2)     0.0102 (16)    −0.0013 (18)
  C11   0.0635 (18)   0.0493 (18)   0.0532 (16)   −0.0004 (15)   0.0089 (14)    −0.0016 (13)
  C12   0.0670 (19)   0.0494 (18)   0.0622 (18)   −0.0037 (15)   0.0066 (15)    −0.0081 (14)
  C13   0.0662 (19)   0.0509 (19)   0.0631 (18)   0.0062 (15)    0.0049 (15)    −0.0036 (14)
  C14   0.0626 (19)   0.0565 (19)   0.0565 (17)   0.0017 (16)    0.0031 (14)    −0.0044 (14)
  C15   0.081 (2)     0.052 (2)     0.082 (2)     0.0008 (18)    −0.0129 (19)   −0.0192 (17)
  C16   0.081 (2)     0.0498 (19)   0.075 (2)     0.0078 (17)    −0.0021 (18)   −0.0101 (16)
  C17   0.075 (2)     0.080 (3)     0.072 (2)     0.013 (2)      0.0000 (18)    −0.0022 (19)
  C18   0.0569 (17)   0.0397 (15)   0.0550 (16)   −0.0012 (13)   0.0060 (13)    −0.0014 (13)
  C19   0.0603 (19)   0.071 (2)     0.0634 (19)   0.0084 (17)    0.0082 (15)    −0.0124 (16)
  C20   0.0579 (18)   0.070 (2)     0.0637 (19)   0.0051 (17)    0.0006 (15)    −0.0079 (17)
  C21   0.0610 (18)   0.0501 (18)   0.0580 (17)   −0.0058 (14)   0.0075 (14)    −0.0049 (13)
  C22   0.0625 (19)   0.077 (2)     0.0589 (18)   0.0100 (18)    0.0112 (15)    −0.0016 (17)
  C23   0.0607 (18)   0.069 (2)     0.0574 (17)   0.0082 (16)    0.0049 (14)    0.0040 (15)
  ----- ------------- ------------- ------------- -------------- -------------- --------------

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

  ---------------------- ------------ ----------------------- ------------
  Br1---C21              1.890 (3)    C20---C21               1.377 (5)
  O1---C14               1.367 (4)    C21---C22               1.377 (5)
  O1---C17               1.419 (5)    C22---C23               1.381 (5)
  N1---C1                1.355 (4)    C2---H2                 0.9300
  N1---C5                1.340 (4)    C6---H6A                0.9700
  C1---C2                1.378 (4)    C6---H6B                0.9700
  C1---C18               1.491 (4)    C7---H7A                0.9700
  C2---C3                1.392 (4)    C7---H7B                0.9700
  C3---C4                1.406 (4)    C8---H8A                0.9700
  C3---C11               1.488 (4)    C8---H8B                0.9700
  C4---C5                1.390 (4)    C9---H9A                0.9700
  C4---C10               1.510 (5)    C9---H9B                0.9700
  C5---C6                1.513 (5)    C10---H10A              0.9700
  C6---C7                1.529 (6)    C10---H10B              0.9700
  C7---C8                1.516 (5)    C12---H12               0.9300
  C8---C9                1.509 (6)    C13---H13               0.9300
  C9---C10               1.530 (6)    C15---H15               0.9300
  C11---C12              1.380 (4)    C16---H16               0.9300
  C11---C16              1.383 (5)    C17---H17A              0.9600
  C12---C13              1.390 (5)    C17---H17B              0.9600
  C13---C14              1.378 (4)    C17---H17C              0.9600
  C14---C15              1.374 (5)    C19---H19               0.9300
  C15---C16              1.375 (6)    C20---H20               0.9300
  C18---C19              1.379 (5)    C22---H22               0.9300
  C18---C23              1.390 (4)    C23---H23               0.9300
  C19---C20              1.381 (5)                            
                                                              
  C14---O1---C17         117.6 (3)    C7---C6---H6B           109.00
  C1---N1---C5           118.3 (2)    H6A---C6---H6B          108.00
  N1---C1---C2           121.2 (3)    C6---C7---H7A           109.00
  N1---C1---C18          115.2 (3)    C6---C7---H7B           109.00
  C2---C1---C18          123.5 (3)    C8---C7---H7A           109.00
  C1---C2---C3           120.9 (3)    C8---C7---H7B           109.00
  C2---C3---C4           118.0 (3)    H7A---C7---H7B          108.00
  C2---C3---C11          118.5 (3)    C7---C8---H8A           108.00
  C4---C3---C11          123.6 (3)    C7---C8---H8B           108.00
  C3---C4---C5           117.7 (3)    C9---C8---H8A           108.00
  C3---C4---C10          122.2 (3)    C9---C8---H8B           108.00
  C5---C4---C10          120.1 (3)    H8A---C8---H8B          107.00
  N1---C5---C4           123.9 (3)    C8---C9---H9A           109.00
  N1---C5---C6           114.3 (3)    C8---C9---H9B           109.00
  C4---C5---C6           121.9 (3)    C10---C9---H9A          109.00
  C5---C6---C7           114.2 (3)    C10---C9---H9B          109.00
  C6---C7---C8           114.4 (3)    H9A---C9---H9B          108.00
  C7---C8---C9           115.9 (3)    C4---C10---H10A         109.00
  C8---C9---C10          114.4 (4)    C4---C10---H10B         109.00
  C4---C10---C9          114.8 (3)    C9---C10---H10A         109.00
  C3---C11---C12         120.8 (3)    C9---C10---H10B         109.00
  C3---C11---C16         121.9 (3)    H10A---C10---H10B       108.00
  C12---C11---C16        117.2 (3)    C11---C12---H12         119.00
  C11---C12---C13        122.0 (3)    C13---C12---H12         119.00
  C12---C13---C14        119.3 (3)    C12---C13---H13         120.00
  O1---C14---C13         124.7 (3)    C14---C13---H13         120.00
  O1---C14---C15         115.9 (3)    C14---C15---H15         120.00
  C13---C14---C15        119.5 (3)    C16---C15---H15         120.00
  C14---C15---C16        120.5 (4)    C11---C16---H16         119.00
  C11---C16---C15        121.6 (4)    C15---C16---H16         119.00
  C1---C18---C19         120.4 (3)    O1---C17---H17A         109.00
  C1---C18---C23         122.2 (3)    O1---C17---H17B         109.00
  C19---C18---C23        117.4 (3)    O1---C17---H17C         109.00
  C18---C19---C20        121.9 (3)    H17A---C17---H17B       109.00
  C19---C20---C21        119.3 (3)    H17A---C17---H17C       110.00
  Br1---C21---C20        119.5 (2)    H17B---C17---H17C       110.00
  Br1---C21---C22        120.0 (2)    C18---C19---H19         119.00
  C20---C21---C22        120.5 (3)    C20---C19---H19         119.00
  C21---C22---C23        119.2 (3)    C19---C20---H20         120.00
  C18---C23---C22        121.7 (3)    C21---C20---H20         120.00
  C1---C2---H2           120.00       C21---C22---H22         120.00
  C3---C2---H2           120.00       C23---C22---H22         120.00
  C5---C6---H6A          109.00       C18---C23---H23         119.00
  C5---C6---H6B          109.00       C22---C23---H23         119.00
  C7---C6---H6A          109.00                               
                                                              
  C17---O1---C14---C13   −3.6 (5)     C3---C4---C5---N1       −0.9 (5)
  C17---O1---C14---C15   176.1 (3)    C4---C5---C6---C7       −62.8 (4)
  C5---N1---C1---C2      −0.3 (5)     N1---C5---C6---C7       117.9 (3)
  C1---N1---C5---C6      179.9 (3)    C5---C6---C7---C8       79.4 (4)
  C1---N1---C5---C4      0.5 (5)      C6---C7---C8---C9       −62.9 (5)
  C5---N1---C1---C18     179.0 (3)    C7---C8---C9---C10      61.7 (5)
  C2---C1---C18---C19    171.9 (3)    C8---C9---C10---C4      −79.3 (4)
  N1---C1---C18---C19    −7.4 (4)     C3---C11---C16---C15    176.5 (3)
  N1---C1---C18---C23    172.3 (3)    C12---C11---C16---C15   0.0 (5)
  N1---C1---C2---C3      0.5 (5)      C3---C11---C12---C13    −176.8 (3)
  C2---C1---C18---C23    −8.4 (5)     C16---C11---C12---C13   −0.2 (5)
  C18---C1---C2---C3     −178.7 (3)   C11---C12---C13---C14   0.3 (5)
  C1---C2---C3---C4      −0.8 (4)     C12---C13---C14---C15   −0.2 (5)
  C1---C2---C3---C11     179.8 (3)    C12---C13---C14---O1    179.4 (3)
  C11---C3---C4---C10    2.3 (5)      O1---C14---C15---C16    −179.6 (3)
  C11---C3---C4---C5     −179.7 (3)   C13---C14---C15---C16   0.0 (5)
  C4---C3---C11---C12    −122.9 (3)   C14---C15---C16---C11   0.1 (6)
  C2---C3---C11---C12    56.5 (4)     C1---C18---C19---C20    −178.5 (3)
  C2---C3---C11---C16    −119.9 (4)   C23---C18---C19---C20   1.8 (5)
  C2---C3---C4---C5      1.0 (4)      C1---C18---C23---C22    179.4 (3)
  C4---C3---C11---C16    60.7 (4)     C19---C18---C23---C22   −0.9 (5)
  C2---C3---C4---C10     −177.1 (3)   C18---C19---C20---C21   −0.9 (6)
  C10---C4---C5---N1     177.3 (3)    C19---C20---C21---Br1   179.1 (3)
  C5---C4---C10---C9     65.7 (4)     C19---C20---C21---C22   −1.0 (5)
  C10---C4---C5---C6     −2.0 (5)     Br1---C21---C22---C23   −178.2 (3)
  C3---C4---C10---C9     −116.2 (4)   C20---C21---C22---C23   1.8 (5)
  C3---C4---C5---C6      179.8 (3)    C21---C22---C23---C18   −0.9 (5)
  ---------------------- ------------ ----------------------- ------------
