(E)-N'-(5-Bromo-2-methoxy-benzyl-idene)-4-chloro-benzohydrazide.

The title Schiff base compound, C(15)H(12)BrClN(2)O(2), crystallizes with two independent mol-ecules in the asymmetric unit. The mol-ecules 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 mol-ecules. The crystal structure is stabilized by inter-molecular 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 = 367.63

Triclinic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.141

S = 1.02

6405 reflections

387 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.64 e Å−3

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.

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

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

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

C15H12BrClN2O2	Z = 4
Mr = 367.63	F000 = 736
Triclinic, P1	Dx = 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 = 2.4–24.5º
c = 20.524 (8) Å	µ = 2.89 mm−1
α = 82.045 (5)º	T = 298 (2) K
β = 83.660 (6)º	Cut from a needle, colorless
γ = 87.573 (5)º	0.20 × 0.20 × 0.18 mm
V = 1516.9 (10) Å3

Bruker SMART APEX CCD area-detector diffractometer	6405 independent reflections
Radiation source: fine-focus sealed tube	3536 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
T = 298(2) K	θmax = 27.0º
ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −9→8
Tmin = 0.596, Tmax = 0.624	k = −12→12
8876 measured reflections	l = −22→26

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.141	w = 1/[σ2(Fo2) + (0.0616P)2 + 0.0769P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
6405 reflections	Δρmax = 0.53 e Å−3
387 parameters	Δρmin = −0.64 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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)

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) ; (ii) .