N'-(3,5-Dibromo-2-hy-droxy-benzyl-idene)-2-methyl-benzohydrazide.

The asymmetric unit of the title compound, C(15)H(12)Br(2)N(2)O(2), contains two independent mol-ecules in which the dihedral angles between the benzene rings are 49.5 (7) and 66.4 (7)°. Intra-molecular O-H⋯N hydrogen bonds generate S(6) ring motifs in each mol-ecule. In the crystal, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains along the b axis.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ▶); Pyta et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Fun et al. (2008 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶); Tang (2010 ▶). For reference bond-length data, see: Allen et al. (1987 ▶) and for hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H12Br2N2O2

M = 412.09

Monoclinic,

a = 18.636 (3) Å

b = 9.606 (2) Å

c = 19.943 (3) Å

β = 113.726 (2)°

V = 3268.4 (10) Å3

Z = 8

Mo Kα radiation

μ = 4.97 mm−1

T = 298 K

0.17 × 0.13 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.486, T max = 0.587

17117 measured reflections

6973 independent reflections

2208 reflections with I > 2σ(I)

R int = 0.116

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.159

S = 0.89

6973 reflections

389 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.49 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048889/sj5065sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048889/sj5065Isup2.hkl

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

C15H12Br2N2O2	F(000) = 1616
Mr = 412.09	Dx = 1.675 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1348 reflections
a = 18.636 (3) Å	θ = 2.5–24.1°
b = 9.606 (2) Å	µ = 4.97 mm−1
c = 19.943 (3) Å	T = 298 K
β = 113.726 (2)°	Block, colourless
V = 3268.4 (10) Å3	0.17 × 0.13 × 0.12 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	6973 independent reflections
Radiation source: fine-focus sealed tube	2208 reflections with I > 2σ(I)
graphite	Rint = 0.116
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→19
Tmin = 0.486, Tmax = 0.587	k = −12→11
17117 measured reflections	l = −25→25

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3
6973 reflections	(Δ/σ)max < 0.001
389 parameters	Δρmax = 0.32 e Å−3
2 restraints	Δρmin = −0.49 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.69344 (6)	0.40876 (10)	0.38431 (6)	0.0971 (4)
Br2	0.72350 (5)	−0.17458 (10)	0.37439 (6)	0.0928 (4)
Br3	−0.06953 (6)	0.85420 (10)	−0.01006 (5)	0.0876 (4)
Br4	−0.12081 (6)	0.29585 (11)	0.04659 (6)	0.0984 (4)
N1	0.4069 (4)	0.1700 (7)	0.3119 (3)	0.0615 (18)
N2	0.3301 (4)	0.1455 (7)	0.3007 (4)	0.0614 (19)
N3	0.1898 (4)	0.6601 (6)	0.2214 (3)	0.0576 (18)
N4	0.2608 (4)	0.6440 (7)	0.2795 (4)	0.0605 (18)
O1	0.5235 (3)	0.3360 (6)	0.3345 (3)	0.0757 (17)
H1	0.4775	0.3154	0.3240	0.114*
O2	0.3146 (3)	0.3703 (6)	0.3204 (3)	0.0781 (18)
O3	0.0844 (3)	0.8048 (6)	0.1160 (3)	0.0726 (16)
H3	0.1266	0.7907	0.1504	0.109*
O4	0.2768 (3)	0.8762 (6)	0.2838 (3)	0.0822 (19)
C1	0.5314 (4)	0.0854 (9)	0.3282 (4)	0.051 (2)
C2	0.5659 (5)	0.2190 (9)	0.3415 (4)	0.057 (2)
C3	0.6469 (5)	0.2318 (8)	0.3630 (4)	0.060 (2)
C4	0.6930 (5)	0.1155 (10)	0.3713 (4)	0.067 (2)
H4A	0.7467	0.1249	0.3851	0.081*
C5	0.6590 (5)	−0.0157 (9)	0.3591 (4)	0.065 (2)
C6	0.5792 (5)	−0.0284 (9)	0.3376 (4)	0.058 (2)
H6	0.5569	−0.1168	0.3292	0.069*
C7	0.4486 (4)	0.0642 (9)	0.3118 (4)	0.057 (2)
H7	0.4265	−0.0242	0.3015	0.069*
C8	0.2854 (5)	0.2545 (10)	0.3053 (4)	0.055 (2)
C9	0.2028 (5)	0.2208 (9)	0.2904 (5)	0.061 (2)
C10	0.1668 (6)	0.2838 (11)	0.3318 (5)	0.088 (3)
C11	0.0869 (7)	0.2519 (13)	0.3119 (7)	0.109 (4)
H11	0.0607	0.2906	0.3384	0.131*
C12	0.0470 (7)	0.1646 (14)	0.2540 (7)	0.111 (4)
H12	−0.0059	0.1473	0.2417	0.133*
C13	0.0832 (6)	0.1029 (9)	0.2144 (6)	0.089 (3)
H13	0.0561	0.0433	0.1757	0.107*
C14	0.1627 (5)	0.1327 (9)	0.2342 (5)	0.073 (3)
H14	0.1888	0.0911	0.2083	0.087*
C15	0.0682 (4)	0.5631 (8)	0.1399 (4)	0.048 (2)
C16	0.0418 (5)	0.6869 (9)	0.1003 (4)	0.054 (2)
C17	−0.0330 (5)	0.6879 (9)	0.0439 (4)	0.059 (2)
C18	−0.0814 (5)	0.5726 (9)	0.0281 (4)	0.066 (2)
H18	−0.1315	0.5755	−0.0090	0.079*
C19	−0.0538 (4)	0.4536 (8)	0.0683 (4)	0.057 (2)
C20	0.0207 (4)	0.4455 (9)	0.1218 (4)	0.056 (2)
H20	0.0394	0.3616	0.1458	0.067*
C21	0.1458 (4)	0.5550 (8)	0.1993 (4)	0.051 (2)
H21	0.1636	0.4695	0.2217	0.061*
C22	0.3020 (5)	0.7621 (9)	0.3066 (4)	0.051 (2)
C23	0.3807 (5)	0.7368 (8)	0.3682 (4)	0.051 (2)
C24	0.4012 (5)	0.8118 (9)	0.4335 (5)	0.065 (2)
C25	0.4759 (7)	0.7929 (11)	0.4871 (5)	0.103 (3)
H25	0.4908	0.8405	0.5312	0.124*
C26	0.5285 (6)	0.7049 (11)	0.4762 (6)	0.102 (3)
H26	0.5786	0.6952	0.5129	0.122*
C27	0.5087 (5)	0.6310 (10)	0.4121 (6)	0.102 (3)
H27	0.5443	0.5710	0.4052	0.122*
C28	0.4339 (5)	0.6489 (9)	0.3583 (5)	0.075 (3)
H28	0.4193	0.6003	0.3145	0.090*
C29	0.2102 (6)	0.3762 (12)	0.3981 (6)	0.138 (5)
H29A	0.2560	0.3286	0.4313	0.208*
H29B	0.1763	0.3970	0.4226	0.208*
H29C	0.2254	0.4613	0.3822	0.208*
C30	0.3438 (6)	0.9038 (10)	0.4487 (5)	0.111 (4)
H30A	0.3303	0.9819	0.4159	0.167*
H30B	0.3673	0.9365	0.4983	0.167*
H30C	0.2974	0.8516	0.4415	0.167*
H4	0.281 (4)	0.559 (3)	0.295 (4)	0.080*
H2	0.309 (4)	0.060 (3)	0.291 (4)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0765 (7)	0.0809 (7)	0.1295 (9)	−0.0250 (6)	0.0369 (7)	−0.0015 (7)
Br2	0.0685 (6)	0.0922 (8)	0.1017 (8)	0.0176 (6)	0.0175 (6)	−0.0253 (6)
Br3	0.0767 (7)	0.0865 (8)	0.0826 (7)	0.0029 (5)	0.0143 (6)	0.0252 (6)
Br4	0.0707 (7)	0.0878 (8)	0.1113 (8)	−0.0274 (6)	0.0101 (6)	−0.0070 (6)
N1	0.051 (5)	0.047 (4)	0.067 (5)	−0.004 (4)	0.004 (4)	0.006 (4)
N2	0.046 (5)	0.045 (5)	0.083 (5)	−0.004 (4)	0.015 (4)	0.007 (4)
N3	0.051 (4)	0.051 (4)	0.059 (5)	−0.013 (4)	0.009 (4)	−0.015 (4)
N4	0.040 (4)	0.056 (5)	0.065 (5)	0.005 (4)	0.000 (4)	0.001 (4)
O1	0.049 (3)	0.062 (4)	0.104 (5)	−0.003 (3)	0.019 (4)	0.015 (3)
O2	0.060 (4)	0.057 (4)	0.107 (5)	0.006 (3)	0.022 (4)	−0.006 (4)
O3	0.060 (4)	0.066 (4)	0.073 (4)	−0.019 (3)	0.006 (3)	0.006 (3)
O4	0.069 (4)	0.047 (4)	0.095 (5)	−0.004 (3)	−0.004 (4)	0.012 (4)
C1	0.050 (5)	0.054 (6)	0.041 (5)	−0.007 (5)	0.009 (4)	−0.006 (4)
C2	0.053 (6)	0.064 (7)	0.041 (5)	−0.002 (5)	0.005 (4)	0.005 (5)
C3	0.060 (6)	0.061 (6)	0.049 (5)	−0.013 (5)	0.010 (5)	−0.001 (4)
C4	0.053 (5)	0.091 (8)	0.055 (6)	0.006 (6)	0.018 (5)	−0.007 (6)
C5	0.062 (6)	0.073 (7)	0.056 (6)	0.010 (5)	0.019 (5)	−0.021 (5)
C6	0.050 (5)	0.063 (6)	0.050 (5)	−0.003 (5)	0.009 (4)	−0.010 (5)
C7	0.042 (5)	0.057 (6)	0.061 (5)	−0.006 (5)	0.009 (4)	0.001 (5)
C8	0.046 (6)	0.053 (6)	0.047 (5)	−0.010 (5)	0.000 (4)	0.006 (5)
C9	0.048 (6)	0.054 (6)	0.075 (7)	−0.011 (5)	0.019 (5)	0.001 (5)
C10	0.087 (8)	0.112 (9)	0.071 (7)	−0.003 (7)	0.038 (7)	0.017 (6)
C11	0.085 (9)	0.168 (12)	0.096 (9)	0.009 (8)	0.058 (8)	0.026 (9)
C12	0.074 (8)	0.164 (13)	0.101 (10)	−0.006 (8)	0.042 (8)	0.051 (9)
C13	0.073 (8)	0.080 (7)	0.105 (8)	−0.008 (6)	0.026 (7)	0.028 (6)
C14	0.048 (6)	0.066 (7)	0.101 (8)	0.005 (5)	0.027 (6)	0.017 (6)
C15	0.055 (5)	0.040 (5)	0.046 (5)	0.006 (4)	0.019 (4)	−0.001 (4)
C16	0.051 (5)	0.060 (6)	0.054 (6)	−0.010 (5)	0.024 (5)	−0.017 (5)
C17	0.046 (5)	0.074 (6)	0.049 (5)	0.009 (5)	0.011 (5)	0.018 (5)
C18	0.052 (5)	0.082 (7)	0.060 (6)	−0.019 (6)	0.018 (5)	−0.007 (5)
C19	0.050 (5)	0.050 (6)	0.057 (6)	−0.004 (4)	0.007 (5)	−0.002 (5)
C20	0.044 (5)	0.064 (6)	0.046 (5)	0.000 (5)	0.004 (4)	−0.010 (4)
C21	0.046 (5)	0.061 (6)	0.034 (5)	0.007 (4)	0.003 (4)	−0.009 (4)
C22	0.049 (5)	0.056 (6)	0.046 (5)	−0.018 (5)	0.016 (5)	−0.009 (5)
C23	0.052 (5)	0.049 (5)	0.049 (6)	−0.008 (4)	0.017 (5)	−0.005 (4)
C24	0.067 (6)	0.073 (6)	0.049 (6)	−0.002 (5)	0.017 (5)	−0.004 (5)
C25	0.104 (9)	0.116 (9)	0.055 (7)	0.005 (8)	−0.004 (7)	−0.018 (6)
C26	0.074 (8)	0.101 (9)	0.093 (9)	−0.013 (7)	−0.007 (7)	−0.013 (7)
C27	0.058 (7)	0.092 (8)	0.114 (9)	0.006 (6)	−0.008 (6)	−0.028 (7)
C28	0.058 (6)	0.078 (7)	0.070 (6)	−0.004 (5)	0.005 (6)	−0.003 (5)
C29	0.124 (10)	0.209 (14)	0.103 (9)	−0.013 (9)	0.067 (8)	−0.035 (9)
C30	0.121 (8)	0.144 (10)	0.078 (7)	0.008 (8)	0.049 (7)	−0.012 (7)

Br1—C3	1.878 (8)	C11—H11	0.9300
Br2—C5	1.890 (8)	C12—C13	1.364 (13)
Br3—C17	1.894 (7)	C12—H12	0.9300
Br4—C19	1.900 (8)	C13—C14	1.402 (11)
N1—C7	1.280 (8)	C13—H13	0.9300
N1—N2	1.377 (8)	C14—H14	0.9300
N2—C8	1.364 (10)	C15—C20	1.391 (9)
N2—H2	0.898 (10)	C15—C16	1.402 (10)
N3—C21	1.263 (8)	C15—C21	1.457 (9)
N3—N4	1.372 (8)	C16—C17	1.396 (10)
N4—C22	1.355 (9)	C17—C18	1.382 (10)
N4—H4	0.898 (10)	C18—C19	1.371 (10)
O1—C2	1.348 (8)	C18—H18	0.9300
O1—H1	0.8200	C19—C20	1.370 (9)
O2—C8	1.221 (8)	C20—H20	0.9300
O3—C16	1.345 (8)	C21—H21	0.9300
O3—H3	0.8200	C22—C23	1.507 (10)
O4—C22	1.207 (8)	C23—C28	1.375 (10)
C1—C6	1.375 (9)	C23—C24	1.400 (10)
C1—C2	1.412 (10)	C24—C25	1.384 (11)
C1—C7	1.457 (9)	C24—C30	1.508 (11)
C2—C3	1.399 (10)	C25—C26	1.378 (12)
C3—C4	1.377 (10)	C25—H25	0.9300
C4—C5	1.387 (10)	C26—C27	1.376 (12)
C4—H4A	0.9300	C26—H26	0.9300
C5—C6	1.378 (9)	C27—C28	1.386 (11)
C6—H6	0.9300	C27—H27	0.9300
C7—H7	0.9300	C28—H28	0.9300
C8—C9	1.481 (10)	C29—H29A	0.9600
C9—C14	1.363 (10)	C29—H29B	0.9600
C9—C10	1.396 (11)	C29—H29C	0.9600
C10—C11	1.411 (13)	C30—H30A	0.9600
C10—C29	1.526 (12)	C30—H30B	0.9600
C11—C12	1.377 (14)	C30—H30C	0.9600
C7—N1—N2	117.1 (6)	C20—C15—C21	119.2 (7)
C8—N2—N1	118.7 (6)	C16—C15—C21	120.8 (7)
C8—N2—H2	119 (5)	O3—C16—C17	119.1 (8)
N1—N2—H2	122 (5)	O3—C16—C15	122.9 (7)
C21—N3—N4	118.3 (7)	C17—C16—C15	118.0 (8)
C22—N4—N3	116.2 (6)	C18—C17—C16	121.8 (8)
C22—N4—H4	122 (5)	C18—C17—Br3	119.6 (6)
N3—N4—H4	122 (5)	C16—C17—Br3	118.6 (7)
C2—O1—H1	109.5	C19—C18—C17	118.5 (7)
C16—O3—H3	109.5	C19—C18—H18	120.8
C6—C1—C2	118.4 (7)	C17—C18—H18	120.8
C6—C1—C7	119.3 (8)	C20—C19—C18	121.8 (7)
C2—C1—C7	122.1 (8)	C20—C19—Br4	119.9 (7)
O1—C2—C3	118.3 (8)	C18—C19—Br4	118.3 (6)
O1—C2—C1	122.3 (7)	C19—C20—C15	119.7 (7)
C3—C2—C1	119.4 (8)	C19—C20—H20	120.2
C4—C3—C2	120.6 (8)	C15—C20—H20	120.2
C4—C3—Br1	119.9 (7)	N3—C21—C15	122.2 (7)
C2—C3—Br1	119.5 (7)	N3—C21—H21	118.9
C3—C4—C5	119.8 (8)	C15—C21—H21	118.9
C3—C4—H4A	120.1	O4—C22—N4	122.5 (8)
C5—C4—H4A	120.1	O4—C22—C23	123.9 (7)
C6—C5—C4	119.6 (8)	N4—C22—C23	113.6 (8)
C6—C5—Br2	121.0 (7)	C28—C23—C24	120.5 (8)
C4—C5—Br2	119.3 (7)	C28—C23—C22	120.2 (7)
C1—C6—C5	122.1 (8)	C24—C23—C22	119.1 (8)
C1—C6—H6	119.0	C25—C24—C23	117.6 (9)
C5—C6—H6	119.0	C25—C24—C30	119.7 (9)
N1—C7—C1	118.5 (7)	C23—C24—C30	122.6 (8)
N1—C7—H7	120.8	C26—C25—C24	121.2 (9)
C1—C7—H7	120.8	C26—C25—H25	119.4
O2—C8—N2	119.5 (7)	C24—C25—H25	119.4
O2—C8—C9	124.9 (9)	C27—C26—C25	121.4 (10)
N2—C8—C9	115.6 (8)	C27—C26—H26	119.3
C14—C9—C10	121.4 (8)	C25—C26—H26	119.3
C14—C9—C8	118.9 (9)	C26—C27—C28	117.7 (9)
C10—C9—C8	119.7 (9)	C26—C27—H27	121.1
C9—C10—C11	116.3 (10)	C28—C27—H27	121.1
C9—C10—C29	123.5 (10)	C23—C28—C27	121.6 (9)
C11—C10—C29	120.1 (11)	C23—C28—H28	119.2
C12—C11—C10	121.4 (11)	C27—C28—H28	119.2
C12—C11—H11	119.3	C10—C29—H29A	109.5
C10—C11—H11	119.3	C10—C29—H29B	109.5
C13—C12—C11	121.6 (11)	H29A—C29—H29B	109.5
C13—C12—H12	119.2	C10—C29—H29C	109.5
C11—C12—H12	119.2	H29A—C29—H29C	109.5
C12—C13—C14	117.5 (10)	H29B—C29—H29C	109.5
C12—C13—H13	121.2	C24—C30—H30A	109.5
C14—C13—H13	121.2	C24—C30—H30B	109.5
C9—C14—C13	121.7 (9)	H30A—C30—H30B	109.5
C9—C14—H14	119.1	C24—C30—H30C	109.5
C13—C14—H14	119.1	H30A—C30—H30C	109.5
C20—C15—C16	120.0 (7)	H30B—C30—H30C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4i	0.90 (1)	1.85 (2)	2.743 (8)	172 (7)
N4—H4···O2	0.90 (1)	1.92 (2)	2.815 (8)	174 (7)
O3—H3···N3	0.82	1.90	2.624 (8)	146
O1—H1···N1	0.82	1.87	2.584 (8)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4i	0.90 (1)	1.85 (2)	2.743 (8)	172 (7)
N4—H4⋯O2	0.90 (1)	1.92 (2)	2.815 (8)	174 (7)
O3—H3⋯N3	0.82	1.90	2.624 (8)	146
O1—H1⋯N1	0.82	1.87	2.584 (8)	145

Symmetry code: (i) .