(E)-N′-(5-Bromo-2-methoxy­benzyl­idene)-4-chloro­benzohydrazide

Lin, H.-W.

doi:10.1107/S1600536808017911

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1275

doi:10.1107/S1600536808017911

Open

access

(E)-N′-(5-Bromo-2-methoxybenzylidene)-4-chlorobenzohydrazide

Hong-Wei Lin ^a ^*

^aDepartment of Chemistry, Huaihua University, Huaihua 418008, People's Republic of China
^*Correspondence e-mail: linhongwei1968@126.com

(Received 8 June 2008; accepted 12 June 2008; online 19 June 2008)

The title Schiff base compound, C₁₅H₁₂BrClN₂O₂, crystallizes with two independent molecules in the asymmetric unit. The molecules adopt an E configuration with respect to the C=N double bond. The dihedral angles between the benzene rings are 24.4 (2) and 9.4 (2)° in the two molecules. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For general background, see: Ali et al. (2005 ); Arıcı et al. (2005 ); Hebbachi & Benali-Cherif (2005 ); Kurtoglu & Ispir (2007 ); Qi et al. (2007 ); Sallam (2007 ); Salmon et al. (2005 ); Sarı et al. (2006 ); Tuncel & Sari (2007 ). For related structures, see: Lin (2007 ); Tang (2007 , 2008 ); Yang et al. (2008 ).

Experimental

Crystal data

C₁₅H₁₂BrClN₂O₂
M_r = 367.63
Triclinic, $[P \overline 1]$
a = 7.636 (3) Å
b = 9.837 (4) Å
c = 20.524 (8) Å
α = 82.045 (5)°
β = 83.660 (6)°
γ = 87.573 (5)°
V = 1516.9 (10) Å³
Z = 4
Mo Kα radiation
μ = 2.89 mm⁻¹
T = 298 (2) K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.596, T_max = 0.624
8876 measured reflections
6405 independent reflections
3536 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.141
S = 1.02
6405 reflections
387 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4ⁱ	0.894 (10)	2.026 (16)	2.900 (4)	165 (4)
N4—H4A⋯O2ⁱⁱ	0.893 (10)	1.994 (18)	2.854 (4)	161 (4)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017911/sj2515sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808017911/sj2515Isup2.hkl

checkCIF report

Comment top

Schiff bases are very important ligands as they can readily form stable complexes with most metal ions (Tuncel & Sari, 2007; Sallam, 2007; Salmon et al., 2005; Ali et al., 2005; Arıcı et al., 2005; Hebbachi & Benali-Cherif, 2005; Sarı et al., 2006). Furthermore, Schiff bases and their metal complexes have excellent biological properties (Kurtoglu & Ispir, 2007; Qi et al., 2007). The author has proeviously reported the crystal structure of the Schiff base compound, isonicotinic acid [1-(3,5-dibromo-2-hydroxyphenyl)methylidene]hydrazide methanol solvate, which shows antibacterial activity (Lin, 2007). As a continuation of work on such compounds, I report herein the crystal structure of the new Schiff base compound, (I), Figure 1.

The two unique molecules of (I) adopt trans configurations about the C═N double bonds. The bond lengths and bond angles are within normal ranges and comparable to those observed in other similar Schiff bases (Tang, 2007, 2008; Yang et al., 2008). The C8–N1 and C23–N3 bond lengths are respectively 1.268 (4) and 1.281 (5) Å, indicating they are double bonds while the C9–N2 and C24–N4 distances are 1.352 (5) and 1.349 (5) Å respectively, indicating some degree of conjugation in the molecules. The dihedral angle between the C1—C6 and C10—C15 benzene rings is 24.4 (2) ° with a 9.4 (2) ° angle between the C16—C21 and C25—C30 rings. The crystal structure is stabilized by intermolecular N–H···O hydrogen bonds (Table 1), forming chains running along the b axis (Figure 2).

Related literature top

For general background, see: Ali et al. (2005); Arıcı et al. (2005); Hebbachi & Benali-Cherif (2005); Kurtoglu & Ispir (2007); Qi et al. (2007); Sallam (2007); Salmon et al. (2005); Sarı et al. (2006); Tuncel & Sari (2007). For related structures, see: Lin (2007); Tang (2007, 2008); Yang et al. (2008).

Experimental top

5-Bromo-2-methoxybenzaldehyde (21.5 mg, 0.1 mmol) and 4-chlorobenzohydrazide (17.0 mg, 0.1 mmol) were dissolved in MeOH (10 ml). The mixture was stirred at room temperature for 5 min to give a colorless solution. Colorless needle-like crystals of (I) were obtained from this solution on standing.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I) with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonds drawn as dashed lines.

(E)-N'-(5-Bromo-2-methoxybenzylidene)-4-chlorobenzohydrazide top

Crystal data top

C₁₅H₁₂BrClN₂O₂	Z = 4
M_r = 367.63	F(000) = 736
Triclinic, P1	D_x = 1.610 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.636 (3) Å	Cell parameters from 2115 reflections
b = 9.837 (4) Å	θ = 2.4–24.5°
c = 20.524 (8) Å	µ = 2.89 mm⁻¹
α = 82.045 (5)°	T = 298 K
β = 83.660 (6)°	Cut from a needle, colorless
γ = 87.573 (5)°	0.20 × 0.20 × 0.18 mm
V = 1516.9 (10) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	6405 independent reflections
Radiation source: fine-focus sealed tube	3536 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 27.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→8
T_min = 0.596, T_max = 0.624	k = −12→12
8876 measured reflections	l = −22→26

Refinement top

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0616P)² + 0.0769P] where P = (F_o² + 2F_c²)/3
6405 reflections	(Δ/σ)_max = 0.001
387 parameters	Δρ_max = 0.53 e Å⁻³
2 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

C₁₅H₁₂BrClN₂O₂	γ = 87.573 (5)°
M_r = 367.63	V = 1516.9 (10) Å³
Triclinic, P1	Z = 4
a = 7.636 (3) Å	Mo Kα radiation
b = 9.837 (4) Å	µ = 2.89 mm⁻¹
c = 20.524 (8) Å	T = 298 K
α = 82.045 (5)°	0.20 × 0.20 × 0.18 mm
β = 83.660 (6)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	6405 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3536 reflections with I > 2σ(I)
T_min = 0.596, T_max = 0.624	R_int = 0.027
8876 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	2 restraints
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.53 e Å⁻³
6405 reflections	Δρ_min = −0.64 e Å⁻³
387 parameters

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
Br1	−0.26007 (7)	0.58987 (6)	0.37080 (3)	0.0799 (2)
Br2	0.70280 (8)	−0.20259 (6)	0.50498 (3)	0.0802 (2)
Cl1	1.33371 (15)	0.53500 (15)	0.06070 (7)	0.0791 (4)
Cl2	0.17724 (17)	0.08183 (14)	1.11711 (6)	0.0720 (4)
O1	0.0684 (3)	0.0824 (3)	0.26908 (15)	0.0538 (8)
O2	0.5295 (4)	0.6554 (3)	0.20845 (15)	0.0540 (8)
O3	0.7291 (4)	0.3334 (3)	0.61136 (16)	0.0647 (9)
O4	0.3751 (4)	−0.1646 (3)	0.83186 (14)	0.0564 (8)
N1	0.3455 (4)	0.4277 (3)	0.24230 (16)	0.0396 (8)
N2	0.5140 (4)	0.4259 (3)	0.21166 (16)	0.0381 (8)
N3	0.5078 (4)	0.0226 (3)	0.73272 (16)	0.0391 (8)
N4	0.4450 (4)	0.0552 (3)	0.79436 (15)	0.0366 (7)
C1	0.0856 (5)	0.3112 (4)	0.28578 (18)	0.0393 (9)
C2	−0.0160 (5)	0.1942 (4)	0.29267 (19)	0.0428 (10)
C3	−0.1897 (5)	0.1970 (5)	0.3207 (2)	0.0530 (11)
H3	−0.2577	0.1198	0.3235	0.064*
C4	−0.2615 (6)	0.3127 (5)	0.3442 (2)	0.0562 (12)
H4	−0.3773	0.3139	0.3637	0.067*
C5	−0.1607 (6)	0.4277 (4)	0.3388 (2)	0.0491 (11)
C6	0.0089 (5)	0.4277 (4)	0.3099 (2)	0.0450 (10)
H6	0.0742	0.5066	0.3063	0.054*
C7	−0.0205 (6)	−0.0445 (4)	0.2809 (3)	0.0658 (14)
H7A	−0.0422	−0.0726	0.3277	0.099*
H7B	0.0514	−0.1132	0.2609	0.099*
H7C	−0.1306	−0.0331	0.2620	0.099*
C8	0.2686 (5)	0.3138 (4)	0.25389 (18)	0.0386 (9)
H8	0.3261	0.2338	0.2426	0.046*
C9	0.5984 (5)	0.5460 (4)	0.19608 (19)	0.0387 (9)
C10	0.7809 (5)	0.5382 (4)	0.16255 (19)	0.0380 (9)
C11	0.8303 (6)	0.4472 (4)	0.1180 (2)	0.0543 (12)
H11	0.7496	0.3855	0.1094	0.065*
C12	1.0006 (6)	0.4474 (4)	0.0860 (2)	0.0619 (13)
H12	1.0331	0.3881	0.0549	0.074*
C13	1.1199 (5)	0.5355 (4)	0.1006 (2)	0.0503 (11)
C14	1.0735 (6)	0.6255 (4)	0.1447 (2)	0.0519 (11)
H14	1.1560	0.6848	0.1542	0.062*
C15	0.9042 (5)	0.6280 (4)	0.1750 (2)	0.0470 (10)
H15	0.8718	0.6909	0.2044	0.056*
C16	0.6500 (5)	0.1030 (4)	0.62592 (19)	0.0388 (9)
C17	0.7266 (5)	0.2153 (4)	0.5841 (2)	0.0480 (10)
C18	0.7957 (6)	0.1997 (5)	0.5206 (2)	0.0634 (13)
H18	0.8470	0.2738	0.4931	0.076*
C19	0.7896 (6)	0.0768 (5)	0.4976 (2)	0.0650 (13)
H19	0.8363	0.0673	0.4546	0.078*
C20	0.7141 (5)	−0.0335 (5)	0.5381 (2)	0.0530 (11)
C21	0.6451 (5)	−0.0205 (4)	0.6024 (2)	0.0455 (10)
H21	0.5954	−0.0957	0.6295	0.055*
C22	0.7650 (8)	0.4582 (5)	0.5692 (3)	0.0902 (19)
H22A	0.8828	0.4539	0.5477	0.135*
H22B	0.7535	0.5332	0.5949	0.135*
H22C	0.6829	0.4721	0.5365	0.135*
C23	0.5758 (5)	0.1230 (4)	0.69281 (19)	0.0390 (9)
H23	0.5779	0.2091	0.7065	0.047*
C24	0.3841 (5)	−0.0456 (4)	0.8418 (2)	0.0394 (9)
C25	0.3300 (5)	−0.0040 (4)	0.90879 (19)	0.0356 (9)
C26	0.2364 (5)	−0.0993 (4)	0.9552 (2)	0.0505 (11)
H26	0.2062	−0.1820	0.9429	0.061*
C27	0.1892 (6)	−0.0726 (5)	1.0180 (2)	0.0565 (12)
H27	0.1274	−0.1369	1.0485	0.068*
C28	0.2331 (5)	0.0499 (4)	1.0362 (2)	0.0463 (10)
C29	0.3231 (5)	0.1459 (4)	0.9917 (2)	0.0514 (11)
H29	0.3519	0.2287	1.0044	0.062*
C30	0.3706 (5)	0.1186 (4)	0.9278 (2)	0.0455 (10)
H30	0.4307	0.1838	0.8973	0.055*
H2	0.563 (5)	0.345 (2)	0.203 (2)	0.080*
H4A	0.440 (6)	0.1421 (19)	0.803 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0826 (4)	0.0853 (4)	0.0695 (4)	0.0282 (3)	0.0066 (3)	−0.0234 (3)
Br2	0.1092 (5)	0.0691 (4)	0.0665 (4)	0.0134 (3)	−0.0071 (3)	−0.0312 (3)
Cl1	0.0522 (7)	0.1017 (10)	0.0773 (10)	−0.0086 (7)	0.0133 (6)	−0.0042 (8)
Cl2	0.0843 (9)	0.0966 (10)	0.0361 (7)	0.0092 (7)	−0.0019 (6)	−0.0191 (6)
O1	0.0520 (17)	0.0475 (17)	0.063 (2)	−0.0136 (14)	0.0019 (14)	−0.0123 (15)
O2	0.0693 (19)	0.0282 (15)	0.062 (2)	−0.0032 (14)	0.0134 (15)	−0.0118 (14)
O3	0.089 (2)	0.0479 (19)	0.053 (2)	−0.0178 (16)	−0.0013 (16)	0.0053 (16)
O4	0.089 (2)	0.0272 (15)	0.0509 (19)	−0.0125 (14)	0.0168 (15)	−0.0122 (13)
N1	0.0406 (19)	0.0320 (18)	0.045 (2)	−0.0011 (14)	0.0018 (15)	−0.0057 (15)
N2	0.0409 (19)	0.0267 (17)	0.045 (2)	−0.0022 (14)	0.0031 (15)	−0.0049 (15)
N3	0.0456 (19)	0.0354 (17)	0.0360 (19)	−0.0010 (15)	0.0004 (15)	−0.0079 (15)
N4	0.0527 (19)	0.0285 (16)	0.0277 (18)	−0.0052 (15)	0.0038 (14)	−0.0055 (15)
C1	0.044 (2)	0.046 (2)	0.026 (2)	−0.0040 (19)	0.0002 (17)	−0.0007 (18)
C2	0.050 (2)	0.049 (3)	0.030 (2)	−0.004 (2)	−0.0038 (18)	−0.0053 (19)
C3	0.047 (3)	0.063 (3)	0.046 (3)	−0.014 (2)	0.003 (2)	−0.001 (2)
C4	0.043 (2)	0.086 (4)	0.037 (3)	−0.001 (2)	0.0058 (19)	−0.005 (2)
C5	0.052 (3)	0.060 (3)	0.034 (2)	0.010 (2)	−0.0023 (19)	−0.008 (2)
C6	0.049 (2)	0.047 (2)	0.038 (2)	−0.0004 (19)	−0.0029 (19)	−0.005 (2)
C7	0.067 (3)	0.048 (3)	0.085 (4)	−0.017 (2)	−0.015 (3)	−0.009 (3)
C8	0.048 (2)	0.033 (2)	0.035 (2)	0.0020 (18)	−0.0023 (18)	−0.0068 (18)
C9	0.053 (2)	0.030 (2)	0.033 (2)	−0.0063 (18)	0.0004 (18)	−0.0085 (17)
C10	0.049 (2)	0.0258 (19)	0.037 (2)	−0.0038 (17)	−0.0020 (18)	0.0001 (17)
C11	0.058 (3)	0.039 (2)	0.066 (3)	−0.015 (2)	0.011 (2)	−0.016 (2)
C12	0.070 (3)	0.046 (3)	0.068 (3)	−0.009 (2)	0.018 (2)	−0.020 (2)
C13	0.050 (3)	0.047 (3)	0.049 (3)	−0.005 (2)	0.004 (2)	0.007 (2)
C14	0.056 (3)	0.053 (3)	0.046 (3)	−0.020 (2)	−0.008 (2)	0.002 (2)
C15	0.061 (3)	0.041 (2)	0.040 (3)	−0.010 (2)	−0.002 (2)	−0.0085 (19)
C16	0.041 (2)	0.043 (2)	0.031 (2)	−0.0017 (18)	−0.0017 (17)	−0.0009 (19)
C17	0.054 (3)	0.043 (2)	0.046 (3)	−0.001 (2)	−0.004 (2)	−0.002 (2)
C18	0.072 (3)	0.062 (3)	0.047 (3)	−0.002 (2)	0.010 (2)	0.011 (3)
C19	0.077 (3)	0.074 (4)	0.037 (3)	0.007 (3)	0.010 (2)	−0.002 (3)
C20	0.055 (3)	0.058 (3)	0.046 (3)	0.007 (2)	−0.004 (2)	−0.014 (2)
C21	0.049 (2)	0.045 (2)	0.042 (3)	0.0040 (19)	−0.0046 (19)	−0.005 (2)
C22	0.129 (5)	0.054 (3)	0.085 (4)	−0.028 (3)	−0.029 (4)	0.023 (3)
C23	0.045 (2)	0.034 (2)	0.039 (2)	−0.0010 (18)	−0.0025 (18)	−0.0088 (19)
C24	0.042 (2)	0.029 (2)	0.047 (3)	−0.0009 (17)	−0.0016 (18)	−0.0052 (19)
C25	0.039 (2)	0.034 (2)	0.034 (2)	0.0023 (16)	−0.0053 (17)	−0.0058 (18)
C26	0.064 (3)	0.036 (2)	0.050 (3)	−0.010 (2)	0.006 (2)	−0.006 (2)
C27	0.070 (3)	0.050 (3)	0.045 (3)	−0.001 (2)	0.007 (2)	0.003 (2)
C28	0.053 (2)	0.055 (3)	0.030 (2)	0.009 (2)	−0.0051 (19)	−0.007 (2)
C29	0.064 (3)	0.043 (2)	0.050 (3)	−0.001 (2)	−0.006 (2)	−0.019 (2)
C30	0.064 (3)	0.035 (2)	0.036 (2)	−0.0056 (19)	0.0026 (19)	−0.0056 (18)

Geometric parameters (Å, º) top

Br1—C5	1.905 (4)	C10—C15	1.386 (5)
Br2—C20	1.891 (5)	C11—C12	1.390 (6)
Cl1—C13	1.744 (4)	C11—H11	0.9300
Cl2—C28	1.736 (4)	C12—C13	1.367 (6)
O1—C2	1.371 (5)	C12—H12	0.9300
O1—C7	1.424 (5)	C13—C14	1.362 (6)
O2—C9	1.224 (4)	C14—C15	1.372 (6)
O3—C17	1.359 (5)	C14—H14	0.9300
O3—C22	1.419 (5)	C15—H15	0.9300
O4—C24	1.222 (4)	C16—C21	1.372 (5)
N1—C8	1.268 (4)	C16—C17	1.407 (5)
N1—N2	1.369 (4)	C16—C23	1.462 (5)
N2—C9	1.352 (5)	C17—C18	1.379 (6)
N2—H2	0.894 (10)	C18—C19	1.361 (7)
N3—C23	1.281 (5)	C18—H18	0.9300
N3—N4	1.378 (4)	C19—C20	1.378 (6)
N4—C24	1.349 (5)	C19—H19	0.9300
N4—H4A	0.893 (10)	C20—C21	1.385 (6)
C1—C6	1.393 (5)	C21—H21	0.9300
C1—C2	1.397 (5)	C22—H22A	0.9600
C1—C8	1.475 (5)	C22—H22B	0.9600
C2—C3	1.387 (5)	C22—H22C	0.9600
C3—C4	1.367 (6)	C23—H23	0.9300
C3—H3	0.9300	C24—C25	1.498 (5)
C4—C5	1.380 (6)	C25—C30	1.376 (5)
C4—H4	0.9300	C25—C26	1.399 (5)
C5—C6	1.363 (5)	C26—C27	1.356 (6)
C6—H6	0.9300	C26—H26	0.9300
C7—H7A	0.9600	C27—C28	1.375 (6)
C7—H7B	0.9600	C27—H27	0.9300
C7—H7C	0.9600	C28—C29	1.370 (6)
C8—H8	0.9300	C29—C30	1.382 (6)
C9—C10	1.488 (5)	C29—H29	0.9300
C10—C11	1.378 (6)	C30—H30	0.9300

C2—O1—C7	118.0 (3)	C13—C14—H14	120.3
C17—O3—C22	119.0 (4)	C15—C14—H14	120.3
C8—N1—N2	116.5 (3)	C14—C15—C10	121.0 (4)
C9—N2—N1	118.4 (3)	C14—C15—H15	119.5
C9—N2—H2	123 (3)	C10—C15—H15	119.5
N1—N2—H2	118 (3)	C21—C16—C17	119.1 (4)
C23—N3—N4	114.4 (3)	C21—C16—C23	122.3 (4)
C24—N4—N3	119.1 (3)	C17—C16—C23	118.6 (4)
C24—N4—H4A	120 (3)	O3—C17—C18	124.6 (4)
N3—N4—H4A	121 (3)	O3—C17—C16	115.6 (4)
C6—C1—C2	118.0 (4)	C18—C17—C16	119.8 (4)
C6—C1—C8	120.1 (3)	C19—C18—C17	120.7 (4)
C2—C1—C8	122.0 (4)	C19—C18—H18	119.7
O1—C2—C3	124.6 (4)	C17—C18—H18	119.7
O1—C2—C1	115.0 (3)	C18—C19—C20	119.9 (5)
C3—C2—C1	120.4 (4)	C18—C19—H19	120.1
C4—C3—C2	120.4 (4)	C20—C19—H19	120.1
C4—C3—H3	119.8	C19—C20—C21	120.5 (4)
C2—C3—H3	119.8	C19—C20—Br2	119.4 (4)
C3—C4—C5	119.5 (4)	C21—C20—Br2	120.1 (3)
C3—C4—H4	120.3	C16—C21—C20	120.1 (4)
C5—C4—H4	120.3	C16—C21—H21	119.9
C6—C5—C4	120.9 (4)	C20—C21—H21	119.9
C6—C5—Br1	119.3 (3)	O3—C22—H22A	109.5
C4—C5—Br1	119.8 (3)	O3—C22—H22B	109.5
C5—C6—C1	120.9 (4)	H22A—C22—H22B	109.5
C5—C6—H6	119.6	O3—C22—H22C	109.5
C1—C6—H6	119.6	H22A—C22—H22C	109.5
O1—C7—H7A	109.5	H22B—C22—H22C	109.5
O1—C7—H7B	109.5	N3—C23—C16	120.4 (4)
H7A—C7—H7B	109.5	N3—C23—H23	119.8
O1—C7—H7C	109.5	C16—C23—H23	119.8
H7A—C7—H7C	109.5	O4—C24—N4	122.8 (4)
H7B—C7—H7C	109.5	O4—C24—C25	121.2 (3)
N1—C8—C1	118.4 (3)	N4—C24—C25	116.0 (3)
N1—C8—H8	120.8	C30—C25—C26	118.5 (4)
C1—C8—H8	120.8	C30—C25—C24	124.5 (3)
O2—C9—N2	122.3 (4)	C26—C25—C24	117.0 (3)
O2—C9—C10	121.5 (3)	C27—C26—C25	120.9 (4)
N2—C9—C10	116.2 (3)	C27—C26—H26	119.6
C11—C10—C15	118.8 (4)	C25—C26—H26	119.6
C11—C10—C9	122.3 (3)	C26—C27—C28	119.7 (4)
C15—C10—C9	118.9 (4)	C26—C27—H27	120.1
C10—C11—C12	120.2 (4)	C28—C27—H27	120.1
C10—C11—H11	119.9	C29—C28—C27	120.9 (4)
C12—C11—H11	119.9	C29—C28—Cl2	119.6 (4)
C13—C12—C11	119.5 (4)	C27—C28—Cl2	119.6 (3)
C13—C12—H12	120.3	C28—C29—C30	119.3 (4)
C11—C12—H12	120.3	C28—C29—H29	120.4
C14—C13—C12	121.1 (4)	C30—C29—H29	120.4
C14—C13—Cl1	119.4 (3)	C25—C30—C29	120.8 (4)
C12—C13—Cl1	119.4 (4)	C25—C30—H30	119.6
C13—C14—C15	119.5 (4)	C29—C30—H30	119.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.89 (1)	2.03 (2)	2.900 (4)	165 (4)
N4—H4A···O2ⁱⁱ	0.89 (1)	1.99 (2)	2.854 (4)	161 (4)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂BrClN₂O₂
M_r	367.63
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.636 (3), 9.837 (4), 20.524 (8)
α, β, γ (°)	82.045 (5), 83.660 (6), 87.573 (5)
V (Å³)	1516.9 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.89
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.596, 0.624
No. of measured, independent and observed [I > 2σ(I)] reflections	8876, 6405, 3536
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.141, 1.02
No. of reflections	6405
No. of parameters	387
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.64

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.894 (10)	2.026 (16)	2.900 (4)	165 (4)
N4—H4A···O2ⁱⁱ	0.893 (10)	1.994 (18)	2.854 (4)	161 (4)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1.

Acknowledgements

The author acknowledges Huaihua University for a research grant.

References

Ali, H. M., Kamalul Aripin, N. F. & Ng, S. W. (2005). Acta Cryst. E61, m433–m434. Web of Science CSD CrossRef IUCr Journals Google Scholar
Arıcı, C., Yüzer, D., Atakol, O., Fuess, H. & Svoboda, I. (2005). Acta Cryst. E61, m919–m921. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hebbachi, R. & Benali-Cherif, N. (2005). Acta Cryst. E61, m1188–m1190. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kurtoglu, M. & Ispir, E. (2007). Asian J. Chem. 19, 1239–1245. CAS Google Scholar
Lin, H.-W. (2007). Chin. J. Struct. Chem. 26, 773–776. CAS Google Scholar
Qi, G.-F., Yang, Z.-Y. & Wang, B.-D. (2007). Transition Met. Chem. 32, 233–239. Web of Science CrossRef CAS Google Scholar
Sallam, S. A. (2007). J. Coord. Chem. 60, 951–971. Web of Science CrossRef CAS Google Scholar
Salmon, L., Thuéry, P. & Ephritikhine, M. (2005). Acta Cryst. E61, m2607–m2609. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sarı, M., Atakol, O., Svoboda, I. & Fuess, H. (2006). Acta Cryst. E62, m563–m565. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, C.-B. (2007). Acta Cryst. E63, o4545. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tang, C.-B. (2008). Acta Cryst. E64, o767. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tuncel, M. & Sari, H. (2007). Transition Met. Chem. 32, 803–810. Web of Science CrossRef CAS Google Scholar
Yang, T., Cao, G.-B., Xiang, J.-M. & Zhang, L.-H. (2008). Acta Cryst. E64, o1186. Web of Science CSD CrossRef IUCr Journals Google Scholar