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Acta Crystallogr Sect E Struct Rep OnlineActa Cryst. EActa Crystallographica Section E: Structure Reports Online1600-5368International Union of Crystallography wn233210.1107/S160053680902282XACSEBHS160053680902282XOrganic Papers
               N′-(3,5-Dibromo-2-hydroxy­benzyl­idene)-3,4-methyl­enedioxy­benzohydrazide C15H10Br2N2O4Sang Ya-Li a*Lin Xue-Song aa Department of Chemistry, Chifeng University, Chifeng 024001, People's Republic of ChinaCorrespondence e-mail: lisaburgess@example.org 7 2009 20 6 2009 20 6 2009 65 Pt 7 e090700o1631 o1632 08 6 2009 13 6 2009 © Sang and Lin 20092009This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.A full version of this article is available from Crystallography Journals Online.In the asymmetric unit of the title hydrazone compound, C15H10Br2N2O4, there are two independent mol­ecules. In each mol­ecule, the five-membered ring adopts a flattened envelope conformation; the flap atoms are displaced by 0.114 (2) and 0.219 (2) Å from the planes of the other four atoms. In one mol­ecule the dihedral angle between the two benzene rings is 22.8 (2)°, while in the other it is 40.8 (2)°. Each mol­ecule displays an E configuration with respect to the C=N bond. In both mol­ecules, intra­molecular O—H⋯N hydrogen bonds are observed. In the crystal structure, mol­ecules are linked through inter­molecular N—H⋯O hydrogen bonds, forming chains along the a axis.
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Related literature
For the biological properties of hydrazones, see: Khattab et al. (2005 ▶); Küçükgüzel et al. (2003 ▶); Cukurovali et al. (2006 ▶). For their coordination chemistry, see: Iskander et al. (2001 ▶); Bernhardt et al. (2004 ▶); Aggarwal et al. (1981 ▶); Thomas et al. (1979 ▶). For the crystal structures of other reported hydrazones, see: Fun et al. (2008 ▶); Wei et al. (2009 ▶); Khaledi et al. (2008 ▶); Yang et al. (2008 ▶). For reference structural data, see: Allen et al. (1987 ▶).
         

Experimental

Crystal data

                  C15H10Br2N2O4
                        


                           M
                           r = 442.07

Triclinic, 
                        


                           a = 9.793 (1) Å


                           b = 13.188 (2) Å


                           c = 13.342 (2) Å

α = 76.282 (2)°

β = 78.350 (2)°

γ = 75.911 (2)°


                           V = 1604.5 (4) Å3
                        


                           Z = 4

Mo Kα radiation

μ = 5.07 mm−1
                        


                           T = 298 K

0.23 × 0.21 × 0.21 mm


               

Data collection

                  Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T
                           min = 0.388, T
                           max = 0.416 (expected range = 0.322–0.345)

9190 measured reflections

6633 independent reflections

4090 reflections with I > 2σ(I)


                           R
                           int = 0.026


               

Refinement

                  
                           R[F
                           2 > 2σ(F
                           2)] = 0.049


                           wR(F
                           2) = 0.141


                           S = 0.98

6633 reflections

423 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.55 e Å−3
                        

Δρmin = −0.66 e Å−3
                        


               


Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902282X/wn2332sup1.cif
            

 Structure factors: contains datablocks I. DOI: 10.1107/S160053680902282X/wn2332Isup2.hkl
            

 Additional supplementary materials:  crystallographic information; 3D view; checkCIF report
            

 Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2332).

We are very grateful to Chifeng University for research funding.

supplementary crystallographic 
information

Comment 
Hydrazone compounds have been widely investigated due to their interesting
biological properties, such as antibacterial and antitumor activities (Khattab
et al., 2005; Küçükgüzel et al., 2003;
Cukurovali et
al., 2006).
Furthermore, hydrazones are excellent
ligands in coordination chemistry, forming a large number of metal complexes
(Iskander et al., 2001; Bernhardt et al., 2004;
Aggarwal et
al., 1981; Thomas et al., 1979).
Recently, the crystal structures of a large number of
hydrazone derivatives have been reported (Fun et al., 2008; Wei
et
al., 2009; Khaledi et al., 2008; Yang et al.,
2008).
In this paper, the crystal structure of the new title hydrazone compound
is reported.

In the asymmetric unit
there are two independent molecules (Fig. 1), which assume E
configurations with respect to the C═N bonds.
In each molecule the five-membered ring adopts a flattened
envelope conformation;
the flap atoms C15 and C30 are displaced by 0.114 (2) and 0.219 (2) Å,
respectively, from the planes of the other four atoms.
In one molecule the dihedral angle between the two benzene rings
is 22.8 (2)°; in the other it is 40.8 (2)°.
All bond lengths are within normal values (Allen et al., 1987).
In both molecules,
intramolecular O—H···N hydrogen bonds (Table 1) are observed.
In the crystal structure, molecules are linked through intermolecular N—H···O
hydrogen bonds (Table 1), forming chains along the a axis, as shown in
Fig. 2.


Experimental 
3,4-(Methylenedioxy)benzohydrazide (1.0 mmol, 180.2 mg) and
3,5-dibromo-2-hydroxybenzaldehyde (1.0 mmol, 280.0 mg) were mixed and refluxed
in aqueous ethanol (95% ethanol : 5% water; 50 ml).
The mixture was stirred for 1 h to give a clear colorless
solution.
Colorless crystals of the title compound were formed by slow evaporation of the
solution in air.


Refinement 
H2 attached to N2 and H4A attached to N4 were located in a difference map and
refined with an N—H distance restraint of 0.90 (1) Å.
The other H atoms were
positioned geometrically [d(C—H) = 0.93–0.97 Å, d(O—H) = 0.82 Å], and refined using a riding model, with Uiso(H) =
1.2Ueq(C) and 1.5Ueq(O). The structure contains solvent
accessible voids of 79.0 Å3, which might accommodate a disordered water
molecule.
The maximum residual electron density peak is located 3.28 Å from H21.

Figures
Fig. 1. The molecular structure of the asymmetric unit, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius. The intramolecular O—H···N hydrogen bonds are shown as dashed lines.

Fig. 2. The crystal packing of the title compound. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.

Crystal data
C15H10Br2N2O4	Z = 4	
Mr = 442.07	F(000) = 864	
Triclinic, P1	Dx = 1.830 Mg m−3	
Hall symbol:  -P 1	Mo Kα radiation, λ = 0.71073 Å	
a = 9.793 (1) Å	Cell parameters from 2697 reflections	
b = 13.188 (2) Å	θ = 2.8–25.0°	
c = 13.342 (2) Å	µ = 5.07 mm−1	
α = 76.282 (2)°	T = 298 K	
β = 78.350 (2)°	Block, colorless	
γ = 75.911 (2)°	0.23 × 0.21 × 0.21 mm	
V = 1604.5 (4)  Å3		
Data collection
Bruker SMART CCD area-detector diffractometer	6633 independent reflections	
Radiation source: fine-focus sealed tube	4090 reflections with I > 2σ(I)	
graphite	Rint = 0.026	
ω scans	θmax = 27.0°, θmin = 4.1°	
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12	
Tmin = 0.388, Tmax = 0.416	k = −16→15	
9190 measured reflections	l = −17→11	
Refinement
Refinement on F2	Primary atom site location: structure-invariant direct methods	
Least-squares matrix: full	Secondary atom site location: difference Fourier map	
R[F2 > 2σ(F2)] = 0.049	Hydrogen site location: inferred from neighbouring sites	
wR(F2) = 0.141	H atoms treated by a mixture of independent and constrained refinement	
S = 0.98	w = 1/[σ2(Fo2) + (0.0781P)2]  where P = (Fo2 + 2Fc2)/3	
6633 reflections	(Δ/σ)max < 0.001	
423 parameters	Δρmax = 1.55 e Å−3	
2 restraints	Δρmin = −0.66 e Å−3	
Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.	
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 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 (Å2)
	x	y	z	Uiso*/Ueq		
Br1	0.88068 (7)	−0.00513 (5)	0.23288 (6)	0.0870 (3)		
Br2	0.34278 (8)	0.02682 (5)	0.11846 (5)	0.0719 (2)		
Br3	−0.32989 (6)	0.72142 (5)	1.11784 (4)	0.0662 (2)		
Br4	0.22028 (8)	0.81059 (6)	1.05222 (5)	0.0793 (2)		
O1	0.7359 (3)	0.2022 (3)	0.2943 (3)	0.0472 (8)		
H1	0.6914	0.2499	0.3252	0.071*		
O2	0.6613 (3)	0.4996 (2)	0.3674 (3)	0.0436 (8)		
O3	0.2556 (4)	0.9420 (3)	0.4051 (3)	0.0590 (10)		
O4	0.4456 (4)	0.8602 (3)	0.4941 (3)	0.0544 (9)		
O5	−0.2006 (3)	0.6068 (3)	0.9410 (3)	0.0479 (8)		
H5	−0.1640	0.5740	0.8939	0.072*		
O6	−0.1740 (3)	0.4855 (3)	0.7024 (3)	0.0524 (9)		
O7	0.1423 (4)	0.1701 (3)	0.4070 (3)	0.0612 (10)		
O8	−0.0796 (3)	0.2781 (3)	0.3989 (2)	0.0488 (8)		
N1	0.5281 (4)	0.3734 (3)	0.3031 (3)	0.0369 (8)		
N2	0.4637 (4)	0.4735 (3)	0.3238 (3)	0.0380 (9)		
N3	−0.0003 (4)	0.5372 (3)	0.8002 (3)	0.0347 (8)		
N4	0.0506 (4)	0.4792 (3)	0.7230 (3)	0.0350 (8)		
C1	0.5062 (5)	0.2213 (3)	0.2451 (3)	0.0380 (10)		
C2	0.6449 (5)	0.1653 (3)	0.2556 (3)	0.0379 (10)		
C3	0.6891 (6)	0.0677 (4)	0.2253 (4)	0.0510 (13)		
C4	0.6019 (6)	0.0259 (4)	0.1848 (4)	0.0532 (13)		
H4	0.6347	−0.0397	0.1644	0.064*		
C5	0.4658 (6)	0.0817 (4)	0.1746 (4)	0.0469 (12)		
C6	0.4184 (5)	0.1777 (4)	0.2045 (4)	0.0426 (11)		
H6	0.3258	0.2147	0.1977	0.051*		
C7	0.4504 (5)	0.3269 (4)	0.2715 (4)	0.0406 (11)		
H7	0.3564	0.3604	0.2651	0.049*		
C8	0.5382 (4)	0.5336 (3)	0.3505 (3)	0.0317 (9)		
C9	0.4569 (4)	0.6426 (3)	0.3609 (3)	0.0317 (9)		
C10	0.3485 (5)	0.6950 (3)	0.3049 (3)	0.0384 (10)		
H10	0.3239	0.6611	0.2595	0.046*		
C11	0.2739 (5)	0.7982 (4)	0.3140 (4)	0.0419 (11)		
H11	0.2002	0.8332	0.2761	0.050*		
C12	0.3136 (5)	0.8447 (3)	0.3803 (4)	0.0396 (10)		
C13	0.4260 (5)	0.7940 (3)	0.4349 (3)	0.0358 (10)		
C14	0.4984 (5)	0.6931 (4)	0.4290 (3)	0.0366 (10)		
H14	0.5715	0.6590	0.4678	0.044*		
C15	0.3443 (6)	0.9581 (4)	0.4691 (4)	0.0577 (14)		
H15A	0.2874	0.9781	0.5326	0.069*		
H15B	0.3936	1.0149	0.4326	0.069*		
C16	0.0381 (5)	0.6371 (3)	0.9138 (3)	0.0367 (10)		
C17	−0.1030 (5)	0.6495 (3)	0.9648 (3)	0.0366 (10)		
C18	−0.1420 (5)	0.7085 (4)	1.0440 (3)	0.0440 (11)		
C19	−0.0483 (6)	0.7567 (4)	1.0706 (3)	0.0521 (13)		
H19	−0.0774	0.7972	1.1224	0.062*		
C20	0.0896 (6)	0.7436 (4)	1.0186 (4)	0.0506 (12)		
C21	0.1344 (5)	0.6834 (4)	0.9426 (3)	0.0424 (11)		
H21	0.2289	0.6734	0.9103	0.051*		
C22	0.0877 (5)	0.5754 (3)	0.8309 (3)	0.0364 (10)		
H22	0.1831	0.5642	0.8007	0.044*		
C23	−0.0460 (4)	0.4517 (3)	0.6800 (3)	0.0336 (9)		
C24	0.0118 (4)	0.3775 (3)	0.6071 (3)	0.0317 (9)		
C25	0.1441 (5)	0.3100 (4)	0.6128 (4)	0.0473 (12)		
H25	0.1990	0.3145	0.6603	0.057*		
C26	0.1955 (5)	0.2359 (4)	0.5486 (5)	0.0587 (15)		
H26	0.2835	0.1896	0.5527	0.070*		
C27	0.1127 (5)	0.2339 (4)	0.4800 (4)	0.0415 (11)		
C28	−0.0185 (4)	0.2998 (3)	0.4727 (3)	0.0334 (9)		
C29	−0.0732 (4)	0.3735 (3)	0.5354 (3)	0.0342 (9)		
H29	−0.1619	0.4185	0.5307	0.041*		
C30	0.0117 (6)	0.1849 (4)	0.3679 (4)	0.0559 (14)		
H30A	0.0291	0.1941	0.2924	0.067*		
H30B	−0.0318	0.1234	0.3967	0.067*		
H2	0.377 (3)	0.505 (5)	0.305 (5)	0.080*		
H4A	0.1436 (19)	0.467 (5)	0.697 (4)	0.080*		
Atomic displacement parameters (Å2)
	U11	U22	U33	U12	U13	U23	
Br1	0.0757 (4)	0.0627 (4)	0.1261 (6)	0.0277 (3)	−0.0345 (4)	−0.0524 (4)	
Br2	0.1068 (5)	0.0619 (4)	0.0702 (4)	−0.0450 (3)	−0.0267 (3)	−0.0179 (3)	
Br3	0.0642 (4)	0.0676 (4)	0.0628 (4)	−0.0100 (3)	0.0140 (3)	−0.0288 (3)	
Br4	0.1044 (5)	0.0985 (5)	0.0648 (4)	−0.0527 (4)	−0.0215 (3)	−0.0338 (3)	
O1	0.0423 (18)	0.040 (2)	0.066 (2)	0.0011 (15)	−0.0170 (16)	−0.0261 (16)	
O2	0.0331 (17)	0.0389 (18)	0.064 (2)	−0.0039 (14)	−0.0126 (15)	−0.0191 (15)	
O3	0.065 (2)	0.0368 (19)	0.082 (3)	0.0148 (17)	−0.0351 (19)	−0.0318 (18)	
O4	0.063 (2)	0.045 (2)	0.065 (2)	0.0106 (17)	−0.0285 (18)	−0.0352 (17)	
O5	0.0418 (17)	0.053 (2)	0.056 (2)	−0.0102 (16)	−0.0053 (15)	−0.0247 (16)	
O6	0.0313 (17)	0.062 (2)	0.076 (2)	−0.0016 (15)	−0.0097 (15)	−0.0445 (19)	
O7	0.052 (2)	0.059 (2)	0.088 (3)	0.0105 (17)	−0.0254 (19)	−0.053 (2)	
O8	0.0481 (18)	0.051 (2)	0.056 (2)	0.0064 (15)	−0.0226 (16)	−0.0316 (16)	
N1	0.040 (2)	0.0268 (19)	0.045 (2)	−0.0009 (16)	−0.0092 (16)	−0.0143 (16)	
N2	0.0318 (19)	0.0283 (19)	0.059 (2)	0.0029 (15)	−0.0149 (17)	−0.0211 (17)	
N3	0.0373 (19)	0.036 (2)	0.0343 (19)	−0.0067 (16)	−0.0067 (15)	−0.0141 (16)	
N4	0.0303 (18)	0.038 (2)	0.042 (2)	−0.0048 (16)	−0.0051 (16)	−0.0200 (16)	
C1	0.043 (3)	0.031 (2)	0.045 (3)	−0.004 (2)	−0.011 (2)	−0.0160 (19)	
C2	0.047 (3)	0.030 (2)	0.039 (2)	−0.006 (2)	−0.008 (2)	−0.0133 (19)	
C3	0.060 (3)	0.035 (3)	0.055 (3)	0.005 (2)	−0.012 (2)	−0.014 (2)	
C4	0.077 (4)	0.032 (3)	0.055 (3)	−0.006 (3)	−0.012 (3)	−0.020 (2)	
C5	0.069 (3)	0.038 (3)	0.043 (3)	−0.026 (3)	−0.012 (2)	−0.008 (2)	
C6	0.047 (3)	0.037 (3)	0.047 (3)	−0.014 (2)	−0.006 (2)	−0.009 (2)	
C7	0.037 (2)	0.034 (2)	0.055 (3)	−0.003 (2)	−0.012 (2)	−0.017 (2)	
C8	0.028 (2)	0.032 (2)	0.037 (2)	−0.0064 (18)	−0.0020 (17)	−0.0125 (18)	
C9	0.031 (2)	0.031 (2)	0.035 (2)	−0.0070 (18)	−0.0026 (17)	−0.0096 (18)	
C10	0.042 (2)	0.031 (2)	0.048 (3)	−0.0060 (19)	−0.016 (2)	−0.012 (2)	
C11	0.046 (3)	0.031 (2)	0.051 (3)	0.002 (2)	−0.024 (2)	−0.011 (2)	
C12	0.046 (3)	0.026 (2)	0.045 (3)	0.0014 (19)	−0.008 (2)	−0.0113 (19)	
C13	0.040 (2)	0.035 (2)	0.036 (2)	−0.0028 (19)	−0.0084 (19)	−0.0186 (19)	
C14	0.036 (2)	0.037 (2)	0.039 (2)	−0.0025 (19)	−0.0119 (18)	−0.0128 (19)	
C15	0.067 (3)	0.045 (3)	0.066 (3)	0.009 (3)	−0.023 (3)	−0.033 (3)	
C16	0.047 (3)	0.032 (2)	0.035 (2)	−0.006 (2)	−0.0144 (19)	−0.0099 (18)	
C17	0.041 (2)	0.031 (2)	0.038 (2)	−0.0076 (19)	−0.0064 (19)	−0.0072 (19)	
C18	0.054 (3)	0.035 (3)	0.040 (3)	−0.005 (2)	−0.005 (2)	−0.006 (2)	
C19	0.076 (4)	0.050 (3)	0.033 (3)	−0.013 (3)	−0.005 (2)	−0.016 (2)	
C20	0.071 (3)	0.054 (3)	0.039 (3)	−0.024 (3)	−0.016 (2)	−0.015 (2)	
C21	0.047 (3)	0.049 (3)	0.038 (2)	−0.017 (2)	−0.008 (2)	−0.013 (2)	
C22	0.035 (2)	0.039 (3)	0.037 (2)	−0.0048 (19)	−0.0068 (18)	−0.012 (2)	
C23	0.030 (2)	0.035 (2)	0.039 (2)	−0.0068 (18)	−0.0081 (18)	−0.0116 (19)	
C24	0.029 (2)	0.024 (2)	0.044 (2)	−0.0033 (17)	−0.0066 (18)	−0.0111 (18)	
C25	0.042 (3)	0.047 (3)	0.064 (3)	−0.003 (2)	−0.024 (2)	−0.025 (2)	
C26	0.041 (3)	0.050 (3)	0.097 (4)	0.015 (2)	−0.028 (3)	−0.048 (3)	
C27	0.035 (2)	0.034 (2)	0.063 (3)	−0.0030 (19)	−0.010 (2)	−0.027 (2)	
C28	0.036 (2)	0.031 (2)	0.035 (2)	−0.0048 (18)	−0.0124 (18)	−0.0071 (18)	
C29	0.030 (2)	0.033 (2)	0.042 (2)	−0.0013 (18)	−0.0088 (18)	−0.0134 (19)	
C30	0.058 (3)	0.051 (3)	0.068 (3)	0.004 (3)	−0.021 (3)	−0.037 (3)	
Geometric parameters (Å, °)
Br1—C3	1.899 (5)	C7—H7	0.9300	
Br2—C5	1.893 (5)	C8—C9	1.488 (6)	
Br3—C18	1.892 (5)	C9—C10	1.372 (6)	
Br4—C20	1.895 (5)	C9—C14	1.415 (6)	
O1—C2	1.347 (5)	C10—C11	1.399 (6)	
O1—H1	0.8200	C10—H10	0.9300	
O2—C8	1.226 (5)	C11—C12	1.348 (6)	
O3—C12	1.361 (5)	C11—H11	0.9300	
O3—C15	1.415 (6)	C12—C13	1.387 (6)	
O4—C13	1.377 (5)	C13—C14	1.358 (6)	
O4—C15	1.437 (6)	C14—H14	0.9300	
O5—C17	1.343 (5)	C15—H15A	0.9700	
O5—H5	0.8200	C15—H15B	0.9700	
O6—C23	1.225 (5)	C16—C21	1.396 (6)	
O7—C27	1.377 (5)	C16—C17	1.400 (6)	
O7—C30	1.430 (6)	C16—C22	1.463 (6)	
O8—C28	1.366 (5)	C17—C18	1.396 (6)	
O8—C30	1.428 (5)	C18—C19	1.377 (7)	
N1—C7	1.269 (6)	C19—C20	1.378 (7)	
N1—N2	1.384 (5)	C19—H19	0.9300	
N2—C8	1.345 (5)	C20—C21	1.372 (6)	
N2—H2	0.91 (4)	C21—H21	0.9300	
N3—C22	1.271 (5)	C22—H22	0.9300	
N3—N4	1.370 (5)	C23—C24	1.477 (5)	
N4—C23	1.357 (5)	C24—C25	1.386 (6)	
N4—H4A	0.90 (3)	C24—C29	1.406 (6)	
C1—C6	1.393 (6)	C25—C26	1.388 (6)	
C1—C2	1.396 (6)	C25—H25	0.9300	
C1—C7	1.465 (6)	C26—C27	1.348 (6)	
C2—C3	1.384 (6)	C26—H26	0.9300	
C3—C4	1.371 (7)	C27—C28	1.373 (6)	
C4—C5	1.373 (7)	C28—C29	1.371 (6)	
C4—H4	0.9300	C29—H29	0.9300	
C5—C6	1.362 (6)	C30—H30A	0.9700	
C6—H6	0.9300	C30—H30B	0.9700	
				
C2—O1—H1	109.5	C9—C14—H14	121.7	
C12—O3—C15	106.3 (3)	O3—C15—O4	108.3 (4)	
C13—O4—C15	105.3 (3)	O3—C15—H15A	110.0	
C17—O5—H5	109.5	O4—C15—H15A	110.0	
C27—O7—C30	105.6 (3)	O3—C15—H15B	110.0	
C28—O8—C30	105.7 (3)	O4—C15—H15B	110.0	
C7—N1—N2	115.5 (3)	H15A—C15—H15B	108.4	
C8—N2—N1	120.9 (3)	C21—C16—C17	119.9 (4)	
C8—N2—H2	118 (4)	C21—C16—C22	118.8 (4)	
N1—N2—H2	120 (4)	C17—C16—C22	121.3 (4)	
C22—N3—N4	117.8 (3)	O5—C17—C18	119.3 (4)	
C23—N4—N3	117.6 (3)	O5—C17—C16	122.7 (4)	
C23—N4—H4A	121 (4)	C18—C17—C16	118.0 (4)	
N3—N4—H4A	121 (4)	C19—C18—C17	122.3 (4)	
C6—C1—C2	119.3 (4)	C19—C18—Br3	119.0 (4)	
C6—C1—C7	118.2 (4)	C17—C18—Br3	118.7 (4)	
C2—C1—C7	122.4 (4)	C18—C19—C20	118.4 (4)	
O1—C2—C3	119.3 (4)	C18—C19—H19	120.8	
O1—C2—C1	122.7 (4)	C20—C19—H19	120.8	
C3—C2—C1	118.0 (4)	C21—C20—C19	121.5 (5)	
C4—C3—C2	122.1 (4)	C21—C20—Br4	119.1 (4)	
C4—C3—Br1	119.7 (4)	C19—C20—Br4	119.3 (4)	
C2—C3—Br1	118.0 (4)	C20—C21—C16	119.9 (4)	
C3—C4—C5	119.4 (4)	C20—C21—H21	120.1	
C3—C4—H4	120.3	C16—C21—H21	120.1	
C5—C4—H4	120.3	N3—C22—C16	119.6 (4)	
C6—C5—C4	120.1 (5)	N3—C22—H22	120.2	
C6—C5—Br2	119.4 (4)	C16—C22—H22	120.2	
C4—C5—Br2	120.5 (4)	O6—C23—N4	121.2 (4)	
C5—C6—C1	121.1 (4)	O6—C23—C24	122.4 (4)	
C5—C6—H6	119.4	N4—C23—C24	116.4 (3)	
C1—C6—H6	119.4	C25—C24—C29	120.9 (4)	
N1—C7—C1	121.1 (4)	C25—C24—C23	120.5 (4)	
N1—C7—H7	119.5	C29—C24—C23	118.5 (3)	
C1—C7—H7	119.5	C24—C25—C26	120.8 (4)	
O2—C8—N2	122.4 (4)	C24—C25—H25	119.6	
O2—C8—C9	123.4 (4)	C26—C25—H25	119.6	
N2—C8—C9	114.2 (3)	C27—C26—C25	117.3 (4)	
C10—C9—C14	120.3 (4)	C27—C26—H26	121.4	
C10—C9—C8	122.2 (4)	C25—C26—H26	121.4	
C14—C9—C8	117.5 (4)	C26—C27—C28	123.0 (4)	
C9—C10—C11	121.8 (4)	C26—C27—O7	127.8 (4)	
C9—C10—H10	119.1	C28—C27—O7	109.1 (4)	
C11—C10—H10	119.1	O8—C28—C29	128.4 (4)	
C12—C11—C10	117.1 (4)	O8—C28—C27	110.3 (4)	
C12—C11—H11	121.4	C29—C28—C27	121.3 (4)	
C10—C11—H11	121.4	C28—C29—C24	116.6 (4)	
C11—C12—O3	128.3 (4)	C28—C29—H29	121.7	
C11—C12—C13	121.7 (4)	C24—C29—H29	121.7	
O3—C12—C13	110.0 (4)	O8—C30—O7	107.0 (3)	
C14—C13—O4	128.2 (4)	O8—C30—H30A	110.3	
C14—C13—C12	122.4 (4)	O7—C30—H30A	110.3	
O4—C13—C12	109.4 (4)	O8—C30—H30B	110.3	
C13—C14—C9	116.6 (4)	O7—C30—H30B	110.3	
C13—C14—H14	121.7	H30A—C30—H30B	108.6	
Hydrogen-bond geometry (Å, °)
D—H···A	D—H	H···A	D···A	D—H···A	
O1—H1···N1	0.82	2.00	2.654 (4)	137	
O5—H5···N3	0.82	1.86	2.582 (4)	146	
N2—H2···O6i	0.91 (4)	1.99 (3)	2.833 (5)	155 (6)	
N4—H4A···O2ii	0.90 (3)	2.04 (3)	2.888 (5)	158 (6)	
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.

Table 1 Hydrogen-bond geometry (Å, °)
D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A	
O1—H1⋯N1	0.82	2.00	2.654 (4)	137	
O5—H5⋯N3	0.82	1.86	2.582 (4)	146	
N2—H2⋯O6i	0.91 (4)	1.99 (3)	2.833 (5)	155 (6)	
N4—H4A⋯O2ii	0.90 (3)	2.04 (3)	2.888 (5)	158 (6)	
Symmetry codes: (i) ; (ii) .
==== Refs
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{'source': 'PubMedDataset'}