(E)-3-(4-Bromo­phen­yl)-3-[3-(4-bromo­phen­yl)-1H-pyrazol-1-yl]prop-2-enal

Ramesh, P.; Manikannan, R.; Muthusubramanian, S.; Ravichandran, K.; Ponnuswamy, M.N.

doi:10.1107/S1600536809054749

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o279

https://doi.org/10.1107/S1600536809054749

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(E)-3-(4-Bromophenyl)-3-[3-(4-bromophenyl)-1H-pyrazol-1-yl]prop-2-enal

P. Ramesh,^a Ramaiyan Manikannan,^b S. Muthusubramanian,^b K. Ravichandran ^a and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 17 December 2009; accepted 19 December 2009; online 9 January 2010)

There are two crystallographically independent molecules in the asymmetric unit of the title compound, C₁₈H₁₂Br₂N₂O. In each molecule, one of the bromophenyl rings lies almost in the plane of pyrazole unit [dihedral angles of 5.8 (3)° in the first molecule and and 5.1 (3)° in the second] while the other ring is approximately perpendicular to it [dihedral angles of 80.3 (3) and 76.5 (3)°]. The crystal packing shows intermolecular C—H⋯O interactions. The crystal studied was a racemic twin.

Related literature

For the pharmacological and medicinal properties of pyrazole derivatives, see: Baraldi et al. (1998 ); Bruno et al. (1990 ); Cottineau et al. (2002 ); Londershausen (1996 ); Chen & Li (1998 ); Mishra et al. (1998 ); Smith et al. (2001 ). For a related structure, see: Jin et al. (2004 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₁₂Br₂N₂O
M_r = 432.12
Orthorhombic, P c a 2₁
a = 9.2600 (3) Å
b = 9.3782 (3) Å
c = 37.9965 (4) Å
V = 3299.70 (15) Å³
Z = 8
Mo Kα radiation
μ = 4.92 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.319, T_max = 0.455
17654 measured reflections
5353 independent reflections
3562 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.086
S = 1.01
5353 reflections
416 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.94 e Å⁻³
Δρ_min = −0.68 e Å⁻³
Absolute structure: Flack (1983 ), 1831 Friedel pairs
Flack parameter: 0.226 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8B—H8B⋯O1Bⁱ	0.93	2.50	3.419 (8)	172
Symmetry code: (i) $[x-{\script{1\over 2}}, -y, z]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, (1997 )); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809054749/bt5143sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809054749/bt5143Isup2.hkl

checkCIF report

Comment top

Pyrazole derivatives possess significant antiarrhythmic and sedative (Bruno et al., 1990), hypoglycemic (Cottineau et al., 2002), antiviral (Baraldi et al., 1998), and pesticidal (Londershausen et al., 1996) properties. Some pyrazole derivatives are successfully tested for their antifungal (Chen & Li, 1998), antihistaminic (Mishra et al., 1998) and anti-inflammatory (Smith et al., 2001) activities. The crystallographic study of the title compound has been carried out to establish the molecular structure.

An ORTEP plot of the molecule is shown in Fig. 1. There are two crystallographically independent molecules in the asymmetric unit. One of the bromophenyl rings lies almost in the plane of the pyrazole moiety and the other ring is approximately perpendicular to it [dihidral angles [5.8 (3)° for C15A—C20A ring and 5.1 (3)° for C15B—C20B ring; 80.3 (3)° for C7A—C12A ring and 76.5 (3)° for C7B—C12B ring]. The vinyl aldehyde groups adopt extended conformation [C6A—C13A—C14A—O1A = -177.9 (7)° for molecule A and 179.4 (7)° for molecule B]. The sum of the bond angles at atoms N2A (359.9°) and N2B (360.0°) of the pyrazole ring in both molecules are in accordance with sp² hybridization.

The molecular conformation is stabilized by weak intra molecular C—H···N interactions. The crystal packing shows intermolecular C—H···O interactions. Atom C8B at (x, y, z) donates a proton to atom O1B at (x - 1/2, -y, z), forming a C7 (Bernstein, 1995) zigzag chain running along the a axis as shown in Fig. 2

Related literature top

For the pharmacological and medicinal properties of pyrazole derivatives, see: Baraldi et al. (1998); Bruno et al. (1990); Cottineau et al. (2002); Londershausen (1996); Chen & Li (1998); Mishra et al. (1998); Smith et al. (2001). For a related structure, see: Jin et al. (2004). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

To a mixture of 1-(4-bromophenyl)-1-ethanone N-[(E)-1-(4-bromophenyl)ethylidene] hydrazone (0.003 mole) and 3 ml of dimethyl formamide kept in an ice bath at 0°C, phosphorus oxycholride (0.024 mole) was added dropwise for 5–10 minutes. The reaction mixture was then kept in a microwave oven at 600 W for 30–60 sec. The process of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into crushed ice and extracted with dichloromethane. The organic layer was dried with anhydrous sodium sulfate. The different compounds present in the mixture were separated by column chromatography using petroleum ether and ethyl acetate mixture as eluent. This isolated compound was rectystalized in dichloromethane.

Structure description top

For the pharmacological and medicinal properties of pyrazole derivatives, see: Baraldi et al. (1998); Bruno et al. (1990); Cottineau et al. (2002); Londershausen (1996); Chen & Li (1998); Mishra et al. (1998); Smith et al. (2001). For a related structure, see: Jin et al. (2004). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, (1997)); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Perspective view of one of the two molecules in the asymmetric unit with the atomic numbering and 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the molecules viewed down c–axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

(E)-3-(4-Bromophenyl)-3-[3-(4-bromophenyl)-1H-pyrazol- 1-yl]prop-2-enal top

Crystal data top

C₁₈H₁₂Br₂N₂O	F(000) = 1696
M_r = 432.12	D_x = 1.740 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2356 reflections
a = 9.2600 (3) Å	θ = 2.1–26.7°
b = 9.3782 (3) Å	µ = 4.92 mm⁻¹
c = 37.9965 (4) Å	T = 293 K
V = 3299.70 (15) Å³	Block, colorless
Z = 8	0.30 × 0.20 × 0.16 mm

Data collection top

Bruker Kappa APEXII diffractometer	5353 independent reflections
Radiation source: fine-focus sealed tube	3562 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω and φ scans	θ_max = 26.7°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −9→11
T_min = 0.319, T_max = 0.455	k = −11→8
17654 measured reflections	l = −47→28

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.0332P)² + 2.8025P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.002
5353 reflections	Δρ_max = 0.94 e Å⁻³
416 parameters	Δρ_min = −0.68 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1831 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.226 (12)

Crystal data top

C₁₈H₁₂Br₂N₂O	V = 3299.70 (15) Å³
M_r = 432.12	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 9.2600 (3) Å	µ = 4.92 mm⁻¹
b = 9.3782 (3) Å	T = 293 K
c = 37.9965 (4) Å	0.30 × 0.20 × 0.16 mm

Data collection top

Bruker Kappa APEXII diffractometer	5353 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3562 reflections with I > 2σ(I)
T_min = 0.319, T_max = 0.455	R_int = 0.032
17654 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.086	Δρ_max = 0.94 e Å⁻³
S = 1.01	Δρ_min = −0.68 e Å⁻³
5353 reflections	Absolute structure: Flack (1983), 1831 Friedel pairs
416 parameters	Absolute structure parameter: 0.226 (12)
2 restraints

Special details top

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) top

	x	y	z	U_iso*/U_eq
Br1A	1.06404 (10)	0.03442 (11)	1.04136 (2)	0.0845 (3)
Br1B	−0.30627 (8)	0.54380 (9)	0.52040 (2)	0.0701 (2)
Br2A	0.53252 (8)	0.16474 (8)	0.66987 (2)	0.0689 (2)
Br2B	0.20118 (8)	0.34086 (8)	0.888391 (19)	0.0687 (2)
O1A	0.4407 (6)	0.3862 (6)	0.94905 (14)	0.0893 (18)
O1B	0.2716 (6)	0.0770 (5)	0.61274 (14)	0.0782 (15)
N1A	0.6924 (5)	0.1737 (5)	0.84642 (15)	0.0441 (13)
N1B	0.0394 (5)	0.3223 (5)	0.71192 (13)	0.0386 (12)
N2A	0.7688 (5)	0.1414 (5)	0.87580 (13)	0.0394 (12)
N2B	−0.0373 (5)	0.3565 (5)	0.68274 (13)	0.0401 (12)
C3A	0.8905 (7)	0.0679 (6)	0.86725 (18)	0.0456 (16)
H3A	0.9595	0.0339	0.8829	0.055*
C3B	−0.1573 (6)	0.4349 (6)	0.69043 (19)	0.0427 (16)
H3B	−0.2241	0.4709	0.6745	0.051*
C4A	0.8933 (7)	0.0536 (6)	0.83279 (19)	0.0451 (16)
H4A	0.9637	0.0077	0.8195	0.054*
C4B	−0.1601 (6)	0.4502 (6)	0.72623 (17)	0.0409 (15)
H4B	−0.2292	0.4972	0.7397	0.049*
C5A	0.7689 (6)	0.1212 (6)	0.82008 (16)	0.0357 (14)
C5B	−0.0348 (7)	0.3788 (6)	0.73838 (16)	0.0358 (14)
C6A	0.7229 (7)	0.1875 (6)	0.90911 (18)	0.0466 (17)
C6B	0.0081 (6)	0.3060 (6)	0.64915 (17)	0.0390 (15)
C7A	0.8119 (7)	0.1444 (7)	0.93918 (16)	0.0429 (16)
C7B	−0.0733 (6)	0.3630 (7)	0.61901 (16)	0.0409 (16)
C8A	0.9017 (7)	0.2424 (7)	0.95476 (18)	0.0520 (17)
H8A	0.9111	0.3333	0.9452	0.062*
C8B	−0.1625 (7)	0.2773 (7)	0.59906 (18)	0.0468 (16)
H8B	−0.1745	0.1818	0.6050	0.056*
C9A	0.9776 (8)	0.2055 (8)	0.9845 (2)	0.063 (2)
H9A	1.0377	0.2725	0.9951	0.076*
C9B	−0.2332 (7)	0.3330 (7)	0.57053 (18)	0.0527 (17)
H9B	−0.2960	0.2759	0.5577	0.063*
C10A	0.9667 (7)	0.0750 (8)	0.99855 (18)	0.0523 (17)
C10B	−0.2125 (7)	0.4713 (7)	0.56087 (19)	0.0478 (17)
C11A	0.8816 (9)	−0.0234 (8)	0.9832 (2)	0.059 (2)
H11A	0.8749	−0.1140	0.9930	0.070*
C11B	−0.1234 (7)	0.5587 (7)	0.58027 (18)	0.0486 (17)
H11B	−0.1100	0.6535	0.5738	0.058*
C12A	0.8043 (8)	0.0080 (7)	0.9532 (3)	0.058 (2)
H12A	0.7477	−0.0615	0.9425	0.069*
C12B	−0.0553 (8)	0.5044 (7)	0.6090 (2)	0.053 (2)
H12B	0.0046	0.5631	0.6223	0.064*
C13A	0.6043 (7)	0.2674 (7)	0.91238 (19)	0.0581 (18)
H13A	0.5540	0.2924	0.8921	0.070*
C13B	0.1155 (7)	0.2129 (6)	0.64759 (17)	0.0480 (16)
H13	0.1556	0.1794	0.6685	0.058*
C14A	0.5513 (8)	0.3163 (7)	0.9454 (2)	0.063 (2)
H14A	0.6039	0.2936	0.9655	0.076*
C14B	0.1728 (8)	0.1613 (7)	0.61425 (19)	0.0554 (18)
H14	0.1320	0.1941	0.5934	0.067*
C15A	0.7154 (6)	0.1352 (6)	0.78364 (17)	0.0375 (15)
C15B	0.0164 (6)	0.3646 (6)	0.77424 (17)	0.0360 (14)
C16A	0.7845 (7)	0.0686 (6)	0.75603 (19)	0.0472 (17)
H16A	0.8673	0.0153	0.7604	0.057*
C16B	−0.0520 (7)	0.4315 (6)	0.80212 (18)	0.0428 (16)
H16B	−0.1355	0.4837	0.7978	0.051*
C17A	0.7334 (7)	0.0793 (6)	0.72186 (18)	0.0464 (16)
H17A	0.7822	0.0361	0.7033	0.056*
C17B	−0.0001 (7)	0.4232 (7)	0.83575 (18)	0.0494 (17)
H17B	−0.0479	0.4695	0.8540	0.059*
C18A	0.6105 (7)	0.1544 (6)	0.71609 (16)	0.0420 (15)
C18B	0.1237 (7)	0.3455 (6)	0.84255 (17)	0.0435 (15)
C19A	0.5396 (6)	0.2233 (7)	0.74279 (19)	0.0456 (16)
H19A	0.4566	0.2758	0.7381	0.055*
C19B	0.1903 (6)	0.2769 (7)	0.81560 (18)	0.0470 (17)
H19B	0.2726	0.2231	0.8201	0.056*
C20A	0.5924 (6)	0.2141 (6)	0.77660 (17)	0.0413 (15)
H20A	0.5451	0.2612	0.7948	0.050*
C20B	0.1383 (7)	0.2854 (6)	0.78198 (18)	0.0398 (15)
H20B	0.1858	0.2372	0.7640	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1A	0.0906 (6)	0.1116 (6)	0.0512 (5)	0.0180 (5)	−0.0083 (5)	0.0153 (5)
Br1B	0.0723 (5)	0.0778 (5)	0.0601 (6)	0.0001 (4)	−0.0177 (4)	0.0176 (5)
Br2A	0.0836 (5)	0.0759 (5)	0.0474 (4)	0.0057 (4)	−0.0086 (4)	0.0055 (4)
Br2B	0.0748 (5)	0.0871 (5)	0.0442 (4)	0.0013 (5)	−0.0060 (4)	0.0059 (4)
O1A	0.096 (4)	0.116 (4)	0.056 (3)	0.053 (4)	−0.002 (3)	−0.022 (3)
O1B	0.082 (4)	0.077 (3)	0.075 (4)	0.032 (3)	0.016 (3)	−0.012 (3)
N1A	0.037 (3)	0.049 (3)	0.046 (4)	0.004 (3)	0.009 (3)	0.002 (3)
N1B	0.042 (3)	0.044 (3)	0.029 (3)	0.001 (2)	0.001 (2)	−0.001 (2)
N2A	0.040 (3)	0.044 (3)	0.035 (3)	0.003 (2)	0.003 (3)	−0.001 (2)
N2B	0.043 (3)	0.040 (3)	0.038 (3)	0.008 (3)	0.002 (3)	−0.006 (2)
C3A	0.046 (4)	0.044 (4)	0.047 (4)	0.001 (3)	−0.003 (3)	−0.012 (3)
C3B	0.033 (3)	0.036 (4)	0.059 (5)	0.009 (3)	−0.001 (3)	0.002 (3)
C4A	0.049 (4)	0.029 (3)	0.058 (5)	−0.001 (3)	0.003 (4)	−0.013 (4)
C4B	0.033 (3)	0.046 (4)	0.044 (4)	0.005 (3)	0.006 (3)	−0.002 (4)
C5A	0.033 (3)	0.030 (3)	0.044 (4)	−0.002 (3)	0.005 (3)	−0.001 (3)
C5B	0.045 (4)	0.025 (3)	0.038 (4)	−0.007 (3)	0.003 (3)	0.002 (3)
C6A	0.050 (4)	0.044 (4)	0.046 (5)	−0.003 (3)	0.007 (3)	−0.002 (3)
C6B	0.039 (3)	0.041 (4)	0.037 (4)	−0.006 (3)	−0.002 (3)	0.000 (3)
C7A	0.047 (4)	0.045 (4)	0.037 (4)	−0.004 (3)	0.002 (3)	0.002 (3)
C7B	0.045 (4)	0.041 (4)	0.037 (4)	0.004 (3)	0.004 (3)	−0.002 (3)
C8A	0.055 (4)	0.045 (4)	0.055 (4)	−0.004 (3)	−0.012 (4)	0.008 (3)
C8B	0.046 (4)	0.036 (3)	0.058 (4)	−0.009 (3)	−0.004 (3)	−0.002 (3)
C9A	0.057 (4)	0.067 (5)	0.066 (5)	−0.007 (4)	−0.007 (4)	−0.009 (4)
C9B	0.053 (4)	0.053 (4)	0.053 (4)	−0.004 (3)	−0.017 (4)	−0.009 (4)
C10A	0.050 (4)	0.059 (5)	0.048 (4)	0.005 (4)	0.004 (3)	0.006 (4)
C10B	0.046 (4)	0.047 (4)	0.050 (5)	0.002 (3)	−0.007 (3)	0.007 (3)
C11A	0.081 (5)	0.039 (4)	0.056 (5)	0.012 (4)	0.010 (4)	0.017 (4)
C11B	0.058 (4)	0.039 (4)	0.048 (4)	−0.005 (3)	0.000 (4)	0.003 (3)
C12A	0.074 (6)	0.034 (4)	0.064 (6)	−0.007 (3)	−0.001 (5)	0.002 (3)
C12B	0.059 (6)	0.054 (5)	0.046 (5)	−0.010 (3)	−0.013 (4)	−0.001 (3)
C13A	0.059 (5)	0.069 (4)	0.046 (4)	0.011 (4)	0.000 (3)	−0.008 (4)
C13B	0.056 (4)	0.049 (4)	0.039 (4)	0.009 (3)	−0.001 (3)	0.007 (3)
C14A	0.063 (5)	0.078 (5)	0.049 (4)	0.015 (4)	0.000 (3)	−0.012 (4)
C14B	0.063 (5)	0.056 (4)	0.048 (5)	0.010 (4)	0.006 (4)	−0.003 (4)
C15A	0.040 (4)	0.032 (3)	0.041 (4)	−0.008 (3)	0.010 (3)	−0.004 (3)
C15B	0.038 (3)	0.028 (3)	0.042 (4)	−0.003 (3)	0.007 (3)	0.001 (3)
C16A	0.037 (4)	0.046 (4)	0.058 (5)	0.006 (3)	0.003 (3)	−0.006 (4)
C16B	0.043 (4)	0.040 (4)	0.045 (4)	0.004 (3)	−0.002 (3)	−0.004 (4)
C17A	0.052 (4)	0.042 (4)	0.046 (4)	0.004 (3)	0.003 (3)	−0.006 (3)
C17B	0.050 (4)	0.058 (4)	0.040 (4)	0.005 (4)	0.009 (3)	−0.015 (3)
C18A	0.048 (4)	0.035 (3)	0.043 (4)	−0.001 (3)	0.000 (3)	0.007 (3)
C18B	0.045 (4)	0.045 (4)	0.040 (4)	−0.006 (3)	0.000 (3)	0.004 (3)
C19A	0.039 (4)	0.046 (4)	0.052 (5)	0.000 (3)	0.005 (3)	0.003 (3)
C19B	0.039 (4)	0.048 (4)	0.054 (5)	0.006 (3)	0.010 (3)	0.009 (3)
C20A	0.035 (3)	0.047 (4)	0.043 (4)	0.006 (3)	0.009 (3)	−0.001 (3)
C20B	0.046 (3)	0.036 (4)	0.038 (4)	0.002 (3)	0.007 (3)	−0.001 (3)

Geometric parameters (Å, º) top

Br1A—C10A	1.898 (7)	C8B—H8B	0.9300
Br1B—C10B	1.892 (7)	C9A—C10A	1.339 (9)
Br2A—C18A	1.901 (6)	C9A—H9A	0.9300
Br2B—C18B	1.884 (6)	C9B—C10B	1.361 (8)
O1A—C14A	1.224 (8)	C9B—H9B	0.9300
O1B—C14B	1.210 (8)	C10A—C11A	1.347 (10)
N1A—C5A	1.321 (8)	C10B—C11B	1.377 (9)
N1A—N2A	1.356 (7)	C11A—C12A	1.375 (12)
N1B—C5B	1.328 (7)	C11A—H11A	0.9300
N1B—N2B	1.355 (6)	C11B—C12B	1.361 (10)
N2A—N1A	1.356 (7)	C11B—H11B	0.9300
N2A—C3A	1.361 (8)	C12A—H12A	0.9300
N2A—C6A	1.403 (8)	C12B—H12B	0.9300
N2B—N1B	1.355 (6)	C13A—C14A	1.424 (10)
N2B—C3B	1.363 (7)	C13A—H13A	0.9300
N2B—C6B	1.425 (8)	C13B—C14B	1.456 (9)
C3A—C4A	1.316 (9)	C13B—H13	0.9300
C3A—H3A	0.9300	C14A—H14A	0.9300
C3B—C4B	1.368 (8)	C14B—H14	0.9300
C3B—H3B	0.9300	C15A—C16A	1.379 (8)
C4A—C5A	1.401 (9)	C15A—C20A	1.384 (8)
C4A—H4A	0.9300	C15B—C20B	1.382 (8)
C4B—C5B	1.416 (9)	C15B—C16B	1.384 (8)
C4B—H4B	0.9300	C16A—C17A	1.385 (9)
C5A—N1A	1.321 (8)	C16A—H16A	0.9300
C5A—C15A	1.477 (8)	C16B—C17B	1.367 (9)
C5B—N1B	1.328 (7)	C16B—H16B	0.9300
C5B—C15B	1.449 (8)	C17A—C18A	1.356 (8)
C6A—C13A	1.336 (8)	C17A—H17A	0.9300
C6A—C7A	1.465 (9)	C17B—C18B	1.383 (9)
C6B—C13B	1.325 (8)	C17B—H17B	0.9300
C6B—C7B	1.471 (8)	C18A—C19A	1.371 (9)
C7A—C8A	1.374 (9)	C18B—C19B	1.358 (9)
C7A—C12A	1.388 (9)	C19A—C20A	1.377 (9)
C7B—C8B	1.379 (8)	C19A—H19A	0.9300
C7B—C12B	1.389 (9)	C19B—C20B	1.367 (9)
C8A—C9A	1.375 (9)	C19B—H19B	0.9300
C8A—H8A	0.9300	C20A—H20A	0.9300
C8B—C9B	1.370 (9)	C20B—H20B	0.9300

C5A—N1A—N2A	105.1 (5)	C10A—C11A—C12A	121.1 (6)
C5B—N1B—N2B	104.7 (5)	C10A—C11A—H11A	119.4
N1A—N2A—C3A	110.4 (5)	C12A—C11A—H11A	119.4
N1A—N2A—C6A	121.0 (5)	C12B—C11B—C10B	119.0 (6)
C3A—N2A—C6A	128.5 (6)	C12B—C11B—H11B	120.5
N1B—N2B—C3B	112.3 (5)	C10B—C11B—H11B	120.5
N1B—N2B—C6B	120.0 (5)	C11A—C12A—C7A	119.3 (7)
C3B—N2B—C6B	127.7 (5)	C11A—C12A—H12A	120.4
C4A—C3A—N2A	107.8 (6)	C7A—C12A—H12A	120.4
C4A—C3A—H3A	126.1	C11B—C12B—C7B	121.4 (7)
N2A—C3A—H3A	126.1	C11B—C12B—H12B	119.3
N2B—C3B—C4B	106.6 (6)	C7B—C12B—H12B	119.3
N2B—C3B—H3B	126.7	C6A—C13A—C14A	123.1 (7)
C4B—C3B—H3B	126.7	C6A—C13A—H13A	118.5
C3A—C4A—C5A	106.3 (6)	C14A—C13A—H13A	118.5
C3A—C4A—H4A	126.8	C6B—C13B—C14B	122.1 (6)
C5A—C4A—H4A	126.8	C6B—C13B—H13	118.9
C3B—C4B—C5B	105.0 (6)	C14B—C13B—H13	118.9
C3B—C4B—H4B	127.5	O1A—C14A—C13A	124.0 (7)
C5B—C4B—H4B	127.5	O1A—C14A—H14A	118.0
N1A—C5A—C4A	110.4 (6)	C13A—C14A—H14A	118.0
N1A—C5A—C4A	110.4 (6)	O1B—C14B—C13B	122.3 (7)
N1A—C5A—C15A	119.8 (5)	O1B—C14B—H14	118.9
N1A—C5A—C15A	119.8 (5)	C13B—C14B—H14	118.9
C4A—C5A—C15A	129.8 (6)	C16A—C15A—C20A	118.5 (6)
N1B—C5B—C4B	111.4 (6)	C16A—C15A—C5A	121.2 (5)
N1B—C5B—C4B	111.4 (6)	C20A—C15A—C5A	120.3 (6)
N1B—C5B—C15B	120.4 (5)	C20B—C15B—C16B	117.0 (6)
N1B—C5B—C15B	120.4 (5)	C20B—C15B—C5B	121.1 (6)
C4B—C5B—C15B	128.2 (6)	C16B—C15B—C5B	121.9 (6)
C13A—C6A—N2A	120.4 (6)	C15A—C16A—C17A	121.4 (6)
C13A—C6A—C7A	123.0 (6)	C15A—C16A—H16A	119.3
N2A—C6A—C7A	116.6 (5)	C17A—C16A—H16A	119.3
C13B—C6B—N2B	118.7 (6)	C17B—C16B—C15B	121.9 (6)
C13B—C6B—C7B	126.1 (6)	C17B—C16B—H16B	119.1
N2B—C6B—C7B	115.2 (5)	C15B—C16B—H16B	119.1
C8A—C7A—C12A	118.8 (6)	C18A—C17A—C16A	118.4 (6)
C8A—C7A—C6A	119.4 (6)	C18A—C17A—H17A	120.8
C12A—C7A—C6A	121.7 (7)	C16A—C17A—H17A	120.8
C8B—C7B—C12B	118.5 (6)	C16B—C17B—C18B	119.7 (6)
C8B—C7B—C6B	121.5 (6)	C16B—C17B—H17B	120.1
C12B—C7B—C6B	119.8 (6)	C18B—C17B—H17B	120.1
C7A—C8A—C9A	119.7 (6)	C17A—C18A—C19A	121.8 (6)
C7A—C8A—H8A	120.2	C17A—C18A—Br2A	119.7 (5)
C9A—C8A—H8A	120.2	C19A—C18A—Br2A	118.5 (5)
C9B—C8B—C7B	120.0 (6)	C19B—C18B—C17B	119.0 (6)
C9B—C8B—H8B	120.0	C19B—C18B—Br2B	120.9 (5)
C7B—C8B—H8B	120.0	C17B—C18B—Br2B	120.0 (5)
C10A—C9A—C8A	121.3 (7)	C18A—C19A—C20A	119.4 (6)
C10A—C9A—H9A	119.4	C18A—C19A—H19A	120.3
C8A—C9A—H9A	119.4	C20A—C19A—H19A	120.3
C10B—C9B—C8B	120.6 (6)	C18B—C19B—C20B	121.1 (6)
C10B—C9B—H9B	119.7	C18B—C19B—H19B	119.4
C8B—C9B—H9B	119.7	C20B—C19B—H19B	119.4
C9A—C10A—C11A	119.8 (7)	C19A—C20A—C15A	120.4 (6)
C9A—C10A—Br1A	119.3 (6)	C19A—C20A—H20A	119.8
C11A—C10A—Br1A	120.8 (6)	C15A—C20A—H20A	119.8
C9B—C10B—C11B	120.5 (6)	C19B—C20B—C15B	121.2 (6)
C9B—C10B—Br1B	119.8 (5)	C19B—C20B—H20B	119.4
C11B—C10B—Br1B	119.7 (5)	C15B—C20B—H20B	119.4

C5A—N1A—N2A—C3A	−0.8 (6)	C8B—C9B—C10B—Br1B	177.8 (5)
C5A—N1A—N2A—C6A	176.8 (5)	C9A—C10A—C11A—C12A	−0.5 (12)
C5B—N1B—N2B—C3B	0.7 (6)	Br1A—C10A—C11A—C12A	176.3 (6)
C5B—N1B—N2B—C6B	−176.9 (5)	C9B—C10B—C11B—C12B	0.7 (10)
N1A—N2A—C3A—C4A	0.4 (7)	Br1B—C10B—C11B—C12B	−179.1 (6)
N1A—N2A—C3A—C4A	0.4 (7)	C10A—C11A—C12A—C7A	−1.5 (12)
C6A—N2A—C3A—C4A	−176.9 (6)	C8A—C7A—C12A—C11A	2.9 (11)
N1B—N2B—C3B—C4B	−1.1 (6)	C6A—C7A—C12A—C11A	−174.8 (7)
N1B—N2B—C3B—C4B	−1.1 (6)	C10B—C11B—C12B—C7B	0.3 (11)
C6B—N2B—C3B—C4B	176.3 (6)	C8B—C7B—C12B—C11B	0.0 (11)
N2A—C3A—C4A—C5A	0.2 (7)	C6B—C7B—C12B—C11B	176.8 (7)
N2B—C3B—C4B—C5B	0.9 (7)	N2A—C6A—C13A—C14A	179.3 (6)
N2A—N1A—C5A—C4A	0.9 (6)	C7A—C6A—C13A—C14A	−1.2 (10)
N2A—N1A—C5A—C15A	178.9 (5)	N2B—C6B—C13B—C14B	−177.0 (5)
C3A—C4A—C5A—N1A	−0.7 (7)	C7B—C6B—C13B—C14B	4.0 (10)
C3A—C4A—C5A—C15A	−178.5 (6)	C6A—C13A—C14A—O1A	−177.9 (7)
N2B—N1B—C5B—C4B	−0.1 (6)	C6B—C13B—C14B—O1B	179.4 (7)
N2B—N1B—C5B—C15B	−179.4 (5)	N1A—C5A—C15A—C16A	−173.0 (5)
C3B—C4B—C5B—N1B	−0.5 (7)	C4A—C5A—C15A—C16A	4.7 (9)
C3B—C4B—C5B—N1B	−0.5 (7)	N1A—C5A—C15A—C20A	5.9 (8)
C3B—C4B—C5B—C15B	178.7 (6)	C4A—C5A—C15A—C20A	−176.4 (6)
N1A—N2A—C6A—C13A	−1.6 (8)	N1B—C5B—C15B—C20B	−3.8 (8)
C3A—N2A—C6A—C13A	175.4 (6)	C4B—C5B—C15B—C20B	177.0 (6)
N1A—N2A—C6A—C7A	178.9 (5)	N1B—C5B—C15B—C16B	174.8 (5)
C3A—N2A—C6A—C7A	−4.1 (9)	C4B—C5B—C15B—C16B	−4.4 (9)
N1B—N2B—C6B—C13B	7.6 (8)	C20A—C15A—C16A—C17A	0.0 (8)
C3B—N2B—C6B—C13B	−169.6 (6)	C5A—C15A—C16A—C17A	178.9 (6)
N1B—N2B—C6B—C7B	−173.3 (5)	C20B—C15B—C16B—C17B	1.5 (9)
C3B—N2B—C6B—C7B	9.5 (8)	C5B—C15B—C16B—C17B	−177.1 (6)
C13A—C6A—C7A—C8A	−75.2 (8)	C15A—C16A—C17A—C18A	−1.7 (9)
N2A—C6A—C7A—C8A	104.3 (7)	C15B—C16B—C17B—C18B	−0.3 (10)
C13A—C6A—C7A—C12A	102.4 (9)	C16A—C17A—C18A—C19A	2.4 (9)
N2A—C6A—C7A—C12A	−78.1 (8)	C16A—C17A—C18A—Br2A	−177.3 (5)
C13B—C6B—C7B—C8B	67.2 (9)	C16B—C17B—C18B—C19B	−1.1 (9)
N2B—C6B—C7B—C8B	−111.8 (6)	C16B—C17B—C18B—Br2B	177.0 (5)
C13B—C6B—C7B—C12B	−109.5 (8)	C17A—C18A—C19A—C20A	−1.3 (9)
N2B—C6B—C7B—C12B	71.5 (8)	Br2A—C18A—C19A—C20A	178.4 (5)
C12A—C7A—C8A—C9A	−2.4 (10)	C17B—C18B—C19B—C20B	1.1 (9)
C6A—C7A—C8A—C9A	175.4 (6)	Br2B—C18B—C19B—C20B	−176.9 (5)
C12B—C7B—C8B—C9B	−1.3 (10)	C18A—C19A—C20A—C15A	−0.5 (9)
C6B—C7B—C8B—C9B	−178.0 (6)	C16A—C15A—C20A—C19A	1.1 (8)
C7A—C8A—C9A—C10A	0.5 (11)	C5A—C15A—C20A—C19A	−177.8 (5)
C7B—C8B—C9B—C10B	2.4 (10)	C18B—C19B—C20B—C15B	0.2 (9)
C8A—C9A—C10A—C11A	1.0 (11)	C16B—C15B—C20B—C19B	−1.5 (8)
C8A—C9A—C10A—Br1A	−175.8 (5)	C5B—C15B—C20B—C19B	177.2 (5)
C8B—C9B—C10B—C11B	−2.0 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13A—H13A···N1A	0.93	2.43	2.779 (9)	102
C13B—H13···N1B	0.93	2.38	2.743 (8)	103
C8B—H8B···O1Bⁱ	0.93	2.50	3.419 (8)	172

Symmetry code: (i) x−1/2, −y, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₂Br₂N₂O
M_r	432.12
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	9.2600 (3), 9.3782 (3), 37.9965 (4)
V (Å³)	3299.70 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	4.92
Crystal size (mm)	0.30 × 0.20 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.319, 0.455
No. of measured, independent and observed [I > 2σ(I)] reflections	17654, 5353, 3562
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.086, 1.01
No. of reflections	5353
No. of parameters	416
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.94, −0.68
Absolute structure	Flack (1983), 1831 Friedel pairs
Absolute structure parameter	0.226 (12)

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, (1997)), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13A—H13A···N1A	0.93	2.43	2.779 (9)	102.2
C13B—H13···N1B	0.93	2.38	2.743 (8)	102.8
C8B—H8B···O1Bⁱ	0.93	2.50	3.419 (8)	171.6

Symmetry code: (i) x−1/2, −y, z.

Acknowledgements

PR thanks Dr Babu Varghese, SAIF, IIT-Madras, Chennai, India, for his help with the data collection.

References

Baraldi, P. G., Manfredini, S., Romagnoli, R., Stevanato, L., Zaid, A. N. & Manservigi, R. (1998). Nucleosides Nucleotides, 17, 2165–2171. Web of Science CrossRef CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruno, O., Bondavalli, F., Ranise, A., Schenone, P., Losasso, C., Cilenti, L., Matera, C. & Marmo, E. (1990). Il Farmaco, 45, 147–66. CAS PubMed Web of Science Google Scholar
Chen, H. S. & Li, Z. M. (1998). Chem. J. Chin. Univ. 19, 572–576. CAS Google Scholar
Cottineau, B., Toto, P., Marot, C., Pipaud, A. & Chenault, J. (2002). Bioorg. Med. Chem. 12, 2105–2108. CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Jin, Z.-M., Li, L., Li, M.-C., Hu, M.-L. & Shen, L. (2004). Acta Cryst. C60, o642–o643. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Londershausen, M. (1996). Pestic. Sci. 48, 269–274. CrossRef CAS Google Scholar
Mishra, P. D., Wahidullah, S. & Kamat, S. Y. (1998). Indian J. Chem. Sect. B, 37, 199–200. Google Scholar
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Smith, S. R., Denhardt, G. & Terminelli, C. (2001). Eur. J. Pharmacol. 432, 107–119. Web of Science CrossRef PubMed CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar