N'-[(E)-1-(5-Bromo-2-hy-droxy-phen-yl)ethyl-idene]-4-nitro-benzohydrazide.

The title compound, C(15)H(12)BrN(3)O(4), displays a trans conformation with respect to the C=N double bond. The central atoms around the C=N double bond are not coplanar, in contrast to the aromatic rings, which exhibit a dihedral angle of 1.80 (4)° between their mean planes. An intra-molecular O-H⋯N hydrogen bond occurs. In the crystal, mol-ecules are connected via inter-molecular N-H⋯O hydrogen bonding into chains along the a axis.

Related literature

For the coordination properties of aroylhydrazones, see: Ali et al. (2004 ▶); Carcelli et al. (1995 ▶); Zhang et al. (2011 ▶); Zheng et al. (2008 ▶).

Experimental

Crystal data

C15H12BrN3O4

M = 378.19

Orthorhombic,

a = 40.381 (13) Å

b = 5.0598 (16) Å

c = 7.168 (2) Å

V = 1464.5 (8) Å3

Z = 4

Mo Kα radiation

μ = 2.83 mm−1

T = 298 K

0.35 × 0.23 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.441, T max = 0.689

6753 measured reflections

2520 independent reflections

2074 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.157

S = 0.95

2520 reflections

210 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.95 e Å−3

Δρmin = −0.75 e Å−3

Absolute structure: Flack (1983), 1075 Friedel pairs

Flack parameter: 0.01 (2)

Data collection: SMART (Bruker, 1996 ▶); cell refinement: SAINT (Bruker, 1996 ▶); 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: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023609/zq2106sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023609/zq2106Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023609/zq2106Isup3.cml

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

C15H12BrN3O4	F(000) = 760
Mr = 378.19	Dx = 1.715 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2077 reflections
a = 40.381 (13) Å	θ = 3.0–23.4°
b = 5.0598 (16) Å	µ = 2.83 mm−1
c = 7.168 (2) Å	T = 298 K
V = 1464.5 (8) Å3	Block, red
Z = 4	0.35 × 0.23 × 0.14 mm

Bruker SMART CCD area-detector diffractometer	2520 independent reflections
Radiation source: fine-focus sealed tube	2074 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 25.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −39→48
Tmin = 0.441, Tmax = 0.689	k = −6→6
6753 measured reflections	l = −7→8

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.120P)2 + 0.2524P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.157	(Δ/σ)max = 0.002
S = 0.95	Δρmax = 0.95 e Å−3
2520 reflections	Δρmin = −0.75 e Å−3
210 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008)
1 restraint	Extinction coefficient: 0.0113 (15)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1075 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.01 (2)

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	0.748669 (14)	0.63795 (13)	0.8107 (3)	0.0527 (3)
N1	0.63083 (12)	0.3604 (9)	0.2325 (8)	0.0407 (12)
N2	0.61516 (12)	0.4290 (9)	0.0655 (7)	0.0398 (12)
H2A	0.6165	0.5855	0.0194	0.048*
N3	0.53035 (13)	0.4393 (12)	−0.7014 (9)	0.0537 (14)
O1	0.63214 (10)	0.0383 (8)	0.5025 (7)	0.0454 (10)
H1	0.6246	0.1078	0.4084	0.068*
O2	0.59928 (11)	0.0029 (8)	0.0369 (7)	0.0534 (12)
O3	0.50841 (18)	0.2902 (13)	−0.7491 (10)	0.094 (2)
O4	0.53936 (16)	0.6248 (14)	−0.7978 (10)	0.087 (2)
C1	0.71150 (13)	0.4542 (11)	0.7103 (8)	0.0383 (13)
C2	0.69852 (14)	0.2403 (12)	0.8090 (10)	0.0460 (13)
H2	0.7078	0.1873	0.9219	0.055*
C3	0.67161 (18)	0.1098 (12)	0.7345 (10)	0.0477 (16)
H3	0.6625	−0.0310	0.8000	0.057*
C4	0.65783 (15)	0.1816 (11)	0.5655 (9)	0.0363 (13)
C5	0.67081 (14)	0.4039 (10)	0.4651 (8)	0.0330 (12)
C6	0.69784 (13)	0.5350 (10)	0.5410 (8)	0.0352 (12)
H6	0.7070	0.6784	0.4781	0.042*
C7	0.65665 (13)	0.4916 (10)	0.2846 (7)	0.0329 (12)
C8	0.67260 (16)	0.7035 (12)	0.1733 (9)	0.0434 (15)
H8A	0.6657	0.6895	0.0455	0.065*
H8B	0.6962	0.6853	0.1804	0.065*
H8C	0.6662	0.8728	0.2218	0.065*
C9	0.59767 (14)	0.2338 (11)	−0.0194 (9)	0.0405 (14)
C10	0.57928 (12)	0.3074 (10)	−0.1896 (10)	0.0353 (11)
C11	0.55293 (16)	0.1454 (12)	−0.2431 (10)	0.0451 (17)
H11	0.5465	0.0060	−0.1667	0.054*
C12	0.53649 (15)	0.1907 (12)	−0.4076 (10)	0.0462 (15)
H12	0.5186	0.0856	−0.4425	0.055*
C13	0.54701 (15)	0.3955 (11)	−0.5200 (9)	0.0411 (14)
C14	0.57239 (14)	0.5633 (11)	−0.4717 (9)	0.0410 (13)
H14	0.5786	0.7022	−0.5492	0.049*
C15	0.58848 (15)	0.5181 (11)	−0.3029 (9)	0.0432 (14)
H15	0.6055	0.6298	−0.2655	0.052*

	U11	U22	U33	U12	U13	U23
Br1	0.0513 (4)	0.0578 (4)	0.0490 (4)	0.0046 (3)	−0.0137 (3)	−0.0030 (5)
N1	0.050 (3)	0.036 (3)	0.035 (3)	0.004 (2)	−0.007 (2)	0.000 (2)
N2	0.053 (3)	0.032 (2)	0.034 (3)	−0.004 (2)	−0.011 (2)	0.002 (2)
N3	0.055 (3)	0.057 (3)	0.050 (4)	0.001 (2)	−0.015 (3)	−0.001 (3)
O1	0.060 (3)	0.030 (2)	0.046 (3)	−0.0088 (19)	0.002 (2)	0.013 (2)
O2	0.077 (3)	0.030 (2)	0.054 (3)	−0.003 (2)	−0.018 (2)	0.001 (2)
O3	0.112 (4)	0.084 (4)	0.086 (6)	−0.029 (4)	−0.056 (4)	0.015 (3)
O4	0.079 (4)	0.115 (5)	0.067 (4)	−0.022 (3)	−0.021 (3)	0.032 (4)
C1	0.046 (3)	0.039 (3)	0.031 (3)	0.007 (2)	−0.004 (2)	−0.010 (3)
C2	0.066 (3)	0.047 (3)	0.025 (3)	0.011 (3)	−0.004 (3)	0.013 (3)
C3	0.072 (4)	0.038 (3)	0.033 (3)	0.005 (3)	0.006 (3)	0.012 (3)
C4	0.044 (3)	0.029 (3)	0.035 (3)	0.005 (2)	0.005 (2)	0.001 (2)
C5	0.037 (3)	0.028 (3)	0.034 (3)	0.005 (2)	0.006 (2)	0.004 (2)
C6	0.044 (3)	0.028 (3)	0.034 (3)	0.000 (2)	0.002 (2)	0.006 (2)
C7	0.044 (3)	0.023 (2)	0.031 (3)	0.003 (2)	0.001 (2)	−0.002 (2)
C8	0.056 (4)	0.041 (3)	0.033 (4)	−0.004 (3)	−0.005 (3)	0.005 (3)
C9	0.039 (3)	0.034 (3)	0.048 (4)	0.000 (3)	0.000 (3)	−0.009 (3)
C10	0.037 (2)	0.030 (2)	0.039 (3)	0.0031 (19)	−0.005 (3)	−0.009 (3)
C11	0.045 (3)	0.035 (3)	0.055 (5)	−0.004 (2)	0.001 (3)	0.004 (3)
C12	0.044 (3)	0.041 (3)	0.053 (4)	−0.007 (3)	−0.009 (3)	0.002 (3)
C13	0.040 (3)	0.044 (3)	0.040 (4)	0.003 (2)	−0.007 (2)	−0.012 (3)
C14	0.048 (3)	0.036 (3)	0.039 (4)	−0.002 (3)	−0.002 (3)	−0.002 (3)
C15	0.047 (3)	0.036 (3)	0.047 (4)	−0.004 (3)	−0.003 (3)	−0.005 (3)

Br1—C1	1.906 (6)	C5—C6	1.388 (8)
N1—C7	1.291 (7)	C5—C7	1.483 (8)
N1—N2	1.397 (7)	C6—H6	0.9300
N2—C9	1.358 (7)	C7—C8	1.484 (8)
N2—H2A	0.8600	C8—H8A	0.9600
N3—O3	1.213 (8)	C8—H8B	0.9600
N3—O4	1.221 (8)	C8—H8C	0.9600
N3—C13	1.480 (8)	C9—C10	1.476 (9)
O1—C4	1.344 (8)	C10—C15	1.391 (9)
O1—H1	0.8200	C10—C11	1.396 (8)
O2—C9	1.238 (7)	C11—C12	1.373 (10)
C1—C6	1.394 (8)	C11—H11	0.9300
C1—C2	1.395 (9)	C12—C13	1.380 (9)
C2—C3	1.380 (10)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.375 (8)
C3—C4	1.381 (10)	C14—C15	1.393 (9)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.435 (8)	C15—H15	0.9300
C7—N1—N2	119.1 (5)	C5—C7—C8	121.2 (5)
C9—N2—N1	116.0 (5)	C7—C8—H8A	109.5
C9—N2—H2A	122.0	C7—C8—H8B	109.5
N1—N2—H2A	122.0	H8A—C8—H8B	109.5
O3—N3—O4	122.4 (7)	C7—C8—H8C	109.5
O3—N3—C13	119.1 (6)	H8A—C8—H8C	109.5
O4—N3—C13	118.5 (5)	H8B—C8—H8C	109.5
C4—O1—H1	109.5	O2—C9—N2	120.8 (6)
C6—C1—C2	121.3 (5)	O2—C9—C10	122.3 (5)
C6—C1—Br1	119.8 (4)	N2—C9—C10	116.7 (5)
C2—C1—Br1	118.9 (5)	C15—C10—C11	119.6 (6)
C3—C2—C1	118.1 (6)	C15—C10—C9	122.8 (5)
C3—C2—H2	121.0	C11—C10—C9	117.5 (5)
C1—C2—H2	121.0	C12—C11—C10	120.4 (6)
C2—C3—C4	122.1 (6)	C12—C11—H11	119.8
C2—C3—H3	119.0	C10—C11—H11	119.8
C4—C3—H3	119.0	C11—C12—C13	118.6 (6)
O1—C4—C3	117.6 (6)	C11—C12—H12	120.7
O1—C4—C5	122.4 (5)	C13—C12—H12	120.7
C3—C4—C5	119.9 (6)	C14—C13—C12	123.1 (6)
C6—C5—C4	117.7 (5)	C14—C13—N3	117.8 (6)
C6—C5—C7	120.1 (5)	C12—C13—N3	119.0 (5)
C4—C5—C7	122.1 (5)	C13—C14—C15	117.7 (6)
C5—C6—C1	120.8 (5)	C13—C14—H14	121.1
C5—C6—H6	119.6	C15—C14—H14	121.1
C1—C6—H6	119.6	C10—C15—C14	120.6 (5)
N1—C7—C5	114.2 (5)	C10—C15—H15	119.7
N1—C7—C8	124.5 (5)	C14—C15—H15	119.7
C7—N1—N2—C9	154.7 (5)	N1—N2—C9—O2	−8.8 (8)
C6—C1—C2—C3	−0.1 (9)	N1—N2—C9—C10	176.3 (5)
Br1—C1—C2—C3	179.9 (5)	O2—C9—C10—C15	−149.2 (6)
C1—C2—C3—C4	1.2 (10)	N2—C9—C10—C15	25.6 (8)
C2—C3—C4—O1	178.5 (6)	O2—C9—C10—C11	26.5 (8)
C2—C3—C4—C5	−2.2 (9)	N2—C9—C10—C11	−158.7 (5)
O1—C4—C5—C6	−178.7 (5)	C15—C10—C11—C12	1.0 (9)
C3—C4—C5—C6	1.9 (8)	C9—C10—C11—C12	−174.9 (5)
O1—C4—C5—C7	0.2 (8)	C10—C11—C12—C13	1.3 (10)
C3—C4—C5—C7	−179.2 (5)	C11—C12—C13—C14	−2.6 (10)
C4—C5—C6—C1	−0.8 (8)	C11—C12—C13—N3	177.5 (6)
C7—C5—C6—C1	−179.8 (5)	O3—N3—C13—C14	178.3 (7)
C2—C1—C6—C5	−0.1 (8)	O4—N3—C13—C14	−1.5 (9)
Br1—C1—C6—C5	179.9 (4)	O3—N3—C13—C12	−1.8 (10)
N2—N1—C7—C5	179.1 (4)	O4—N3—C13—C12	178.4 (7)
N2—N1—C7—C8	−4.0 (8)	C12—C13—C14—C15	1.5 (9)
C6—C5—C7—N1	−177.5 (5)	N3—C13—C14—C15	−178.6 (5)
C4—C5—C7—N1	3.6 (7)	C11—C10—C15—C14	−2.2 (9)
C6—C5—C7—C8	5.5 (8)	C9—C10—C15—C14	173.5 (5)
C4—C5—C7—C8	−173.4 (6)	C13—C14—C15—C10	0.9 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.86	2.23	2.981 (6)	146.
O1—H1···N1	0.82	1.81	2.531 (7)	145.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.86	2.23	2.981 (6)	146
O1—H1⋯N1	0.82	1.81	2.531 (7)	145

Symmetry code: (i) .