N'-(3-Bromo-5-chloro-2-hydroxy-benzyl-idine)-2-hydroxy-benzohydrazide.

In the approximately planar title mol-ecule, C(14)H(10)BrClN(3)O(2), the dihedral angle between the aromatic ring planes is 5.79 (12)°. The conformation is stabilized by intra-molecular O-H⋯N and N-H⋯O hydrogen bonds and an inter-molecular O-H⋯O link leads to chains in the crystal propagating in [001].

Related literature

For similar Schiff bases, see: Hu et al. (2005 ▶); Wu et al. (2006 ▶); Yehye et al. (2008a ▶,b ▶).

Experimental

Crystal data

C14H10BrClN2O3

M = 369.60

Monoclinic,

a = 15.8387 (3) Å

b = 6.9319 (1) Å

c = 12.9951 (3) Å

β = 106.461 (1)°

V = 1368.28 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.21 mm−1

T = 100 (2) K

0.30 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.446, T max = 0.856

12350 measured reflections

3136 independent reflections

2545 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.077

S = 1.02

3136 reflections

202 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038634/hb2857sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038634/hb2857Isup2.hkl

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

C14H10BrClN2O3	F000 = 736
Mr = 369.60	Dx = 1.794 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3691 reflections
a = 15.8387 (3) Å	θ = 3.2–28.2º
b = 6.9319 (1) Å	µ = 3.21 mm−1
c = 12.9951 (3) Å	T = 100 (2) K
β = 106.461 (1)º	Plate, yellow
V = 1368.28 (5) Å3	0.30 × 0.20 × 0.05 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3136 independent reflections
Radiation source: fine-focus sealed tube	2545 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.038
T = 100(2) K	θmax = 27.5º
ω scans	θmin = 1.3º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)	h = −20→20
Tmin = 0.446, Tmax = 0.856	k = −9→8
12350 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difmap and geom
R[F2 > 2σ(F2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0353P)2 + 1.3959P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
3136 reflections	Δρmax = 0.43 e Å−3
202 parameters	Δρmin = −0.41 e Å−3
3 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.

	x	y	z	Uiso*/Ueq
Br1	0.145097 (18)	0.43521 (4)	0.04463 (2)	0.02196 (9)
Cl1	−0.04591 (4)	0.45367 (9)	0.33930 (5)	0.01932 (14)
O1	0.48671 (11)	0.8436 (3)	0.72174 (14)	0.0186 (4)
H1O	0.495 (2)	0.837 (5)	0.7879 (9)	0.033 (9)*
O2	0.52114 (12)	0.6952 (3)	0.42779 (14)	0.0224 (4)
O3	0.28679 (12)	0.5844 (3)	0.23371 (14)	0.0184 (4)
H3O	0.3254 (15)	0.616 (4)	0.2897 (15)	0.027 (9)*
N1	0.42237 (13)	0.7471 (3)	0.52022 (16)	0.0142 (4)
H1N	0.4157 (17)	0.778 (4)	0.5825 (12)	0.015 (7)*
N2	0.35545 (13)	0.6804 (3)	0.43620 (16)	0.0154 (4)
C1	0.56768 (15)	0.8577 (4)	0.70555 (19)	0.0140 (5)
C2	0.64075 (16)	0.9151 (4)	0.7881 (2)	0.0163 (5)
H2	0.6343	0.9445	0.8569	0.020*
C3	0.72242 (16)	0.9295 (4)	0.7702 (2)	0.0171 (5)
H3	0.7720	0.9670	0.8271	0.021*
C4	0.73279 (16)	0.8897 (4)	0.6701 (2)	0.0174 (5)
H4	0.7890	0.9010	0.6581	0.021*
C5	0.66035 (16)	0.8333 (4)	0.5875 (2)	0.0158 (5)
H5	0.6674	0.8061	0.5187	0.019*
C6	0.57684 (15)	0.8157 (3)	0.60395 (19)	0.0131 (5)
C7	0.50521 (16)	0.7480 (3)	0.51062 (19)	0.0149 (5)
C8	0.27901 (16)	0.6691 (4)	0.4507 (2)	0.0154 (5)
H8	0.2706	0.7070	0.5174	0.018*
C9	0.20470 (16)	0.5978 (3)	0.3648 (2)	0.0155 (5)
C10	0.21190 (16)	0.5580 (3)	0.2611 (2)	0.0153 (5)
C11	0.13777 (17)	0.4882 (4)	0.1845 (2)	0.0162 (5)
C12	0.05895 (16)	0.4549 (3)	0.2073 (2)	0.0169 (5)
H12	0.0095	0.4062	0.1538	0.020*
C13	0.05363 (16)	0.4941 (4)	0.3096 (2)	0.0163 (5)
C14	0.12487 (17)	0.5652 (3)	0.3880 (2)	0.0171 (5)
H14	0.1197	0.5921	0.4577	0.020*

	U11	U22	U33	U12	U13	U23
Br1	0.02322 (15)	0.02735 (15)	0.01301 (13)	−0.00167 (11)	0.00141 (10)	−0.00143 (11)
Cl1	0.0119 (3)	0.0207 (3)	0.0259 (3)	−0.0026 (2)	0.0063 (2)	−0.0016 (3)
O1	0.0127 (9)	0.0334 (10)	0.0096 (8)	−0.0027 (8)	0.0032 (7)	−0.0009 (8)
O2	0.0184 (9)	0.0369 (11)	0.0111 (9)	0.0009 (8)	0.0027 (7)	−0.0044 (8)
O3	0.0149 (9)	0.0247 (10)	0.0149 (9)	−0.0035 (7)	0.0029 (7)	−0.0025 (8)
N1	0.0129 (10)	0.0201 (11)	0.0079 (10)	−0.0002 (8)	0.0000 (8)	−0.0028 (8)
N2	0.0148 (10)	0.0162 (10)	0.0113 (10)	0.0002 (8)	−0.0027 (8)	−0.0009 (8)
C1	0.0124 (12)	0.0151 (12)	0.0136 (12)	0.0003 (9)	0.0020 (9)	0.0018 (10)
C2	0.0162 (12)	0.0192 (12)	0.0122 (12)	−0.0016 (10)	0.0018 (10)	−0.0003 (10)
C3	0.0131 (12)	0.0181 (12)	0.0176 (12)	−0.0002 (10)	0.0000 (10)	0.0005 (11)
C4	0.0127 (12)	0.0188 (13)	0.0209 (13)	0.0007 (10)	0.0052 (10)	0.0017 (10)
C5	0.0167 (12)	0.0163 (12)	0.0150 (12)	0.0017 (10)	0.0054 (10)	0.0012 (10)
C6	0.0137 (11)	0.0127 (11)	0.0113 (11)	0.0010 (9)	0.0008 (9)	0.0021 (9)
C7	0.0168 (12)	0.0151 (11)	0.0116 (12)	0.0017 (10)	0.0018 (10)	0.0028 (10)
C8	0.0170 (12)	0.0144 (12)	0.0124 (11)	0.0013 (10)	0.0005 (10)	−0.0014 (10)
C9	0.0140 (12)	0.0147 (12)	0.0157 (12)	0.0005 (9)	0.0009 (10)	−0.0004 (10)
C10	0.0144 (12)	0.0133 (12)	0.0177 (12)	0.0022 (9)	0.0038 (10)	0.0040 (10)
C11	0.0185 (13)	0.0147 (11)	0.0132 (12)	0.0014 (10)	0.0011 (10)	0.0004 (10)
C12	0.0140 (12)	0.0152 (12)	0.0175 (13)	−0.0008 (10)	−0.0021 (10)	−0.0002 (10)
C13	0.0126 (12)	0.0132 (11)	0.0224 (13)	0.0007 (9)	0.0038 (10)	0.0010 (10)
C14	0.0188 (12)	0.0150 (12)	0.0166 (12)	0.0020 (10)	0.0037 (10)	0.0003 (10)

Br1—C11	1.890 (3)	C3—H3	0.9500
Cl1—C13	1.749 (3)	C4—C5	1.387 (4)
O1—C1	1.361 (3)	C4—H4	0.9500
O1—H1O	0.833 (10)	C5—C6	1.404 (3)
O2—C7	1.229 (3)	C5—H5	0.9500
O3—C10	1.344 (3)	C6—C7	1.483 (3)
O3—H3O	0.836 (10)	C8—C9	1.459 (3)
N1—C7	1.353 (3)	C8—H8	0.9500
N1—N2	1.369 (3)	C9—C14	1.399 (4)
N1—H1N	0.872 (10)	C9—C10	1.412 (4)
N2—C8	1.279 (3)	C10—C11	1.393 (3)
C1—C2	1.395 (3)	C11—C12	1.382 (4)
C1—C6	1.399 (3)	C12—C13	1.383 (4)
C2—C3	1.382 (4)	C12—H12	0.9500
C2—H2	0.9500	C13—C14	1.379 (4)
C3—C4	1.384 (4)	C14—H14	0.9500
C1—O1—H1O	106 (2)	O2—C7—N1	121.6 (2)
C10—O3—H3O	107 (2)	O2—C7—C6	120.8 (2)
C7—N1—N2	118.7 (2)	N1—C7—C6	117.6 (2)
C7—N1—H1N	117.4 (18)	N2—C8—C9	120.0 (2)
N2—N1—H1N	123.5 (18)	N2—C8—H8	120.0
C8—N2—N1	117.0 (2)	C9—C8—H8	120.0
O1—C1—C2	121.0 (2)	C14—C9—C10	119.8 (2)
O1—C1—C6	119.0 (2)	C14—C9—C8	118.2 (2)
C2—C1—C6	120.0 (2)	C10—C9—C8	122.0 (2)
C3—C2—C1	120.2 (2)	O3—C10—C11	119.1 (2)
C3—C2—H2	119.9	O3—C10—C9	122.8 (2)
C1—C2—H2	119.9	C11—C10—C9	118.0 (2)
C2—C3—C4	120.7 (2)	C12—C11—C10	122.3 (2)
C2—C3—H3	119.6	C12—C11—Br1	118.63 (19)
C4—C3—H3	119.6	C10—C11—Br1	119.05 (19)
C3—C4—C5	119.4 (2)	C11—C12—C13	118.6 (2)
C3—C4—H4	120.3	C11—C12—H12	120.7
C5—C4—H4	120.3	C13—C12—H12	120.7
C4—C5—C6	121.0 (2)	C14—C13—C12	121.3 (2)
C4—C5—H5	119.5	C14—C13—Cl1	119.6 (2)
C6—C5—H5	119.5	C12—C13—Cl1	119.01 (19)
C1—C6—C5	118.7 (2)	C13—C14—C9	119.9 (2)
C1—C6—C7	125.3 (2)	C13—C14—H14	120.0
C5—C6—C7	116.0 (2)	C9—C14—H14	120.0
C7—N1—N2—C8	175.3 (2)	N2—C8—C9—C14	172.3 (2)
O1—C1—C2—C3	−179.7 (2)	N2—C8—C9—C10	−6.4 (4)
C6—C1—C2—C3	−0.5 (4)	C14—C9—C10—O3	−179.4 (2)
C1—C2—C3—C4	0.8 (4)	C8—C9—C10—O3	−0.7 (4)
C2—C3—C4—C5	−0.6 (4)	C14—C9—C10—C11	0.5 (4)
C3—C4—C5—C6	−0.1 (4)	C8—C9—C10—C11	179.2 (2)
O1—C1—C6—C5	179.1 (2)	O3—C10—C11—C12	179.1 (2)
C2—C1—C6—C5	−0.2 (4)	C9—C10—C11—C12	−0.9 (4)
O1—C1—C6—C7	−2.6 (4)	O3—C10—C11—Br1	−0.5 (3)
C2—C1—C6—C7	178.1 (2)	C9—C10—C11—Br1	179.55 (18)
C4—C5—C6—C1	0.4 (4)	C10—C11—C12—C13	0.6 (4)
C4—C5—C6—C7	−178.0 (2)	Br1—C11—C12—C13	−179.88 (18)
N2—N1—C7—O2	1.8 (4)	C11—C12—C13—C14	0.1 (4)
N2—N1—C7—C6	−178.3 (2)	C11—C12—C13—Cl1	179.70 (19)
C1—C6—C7—O2	−172.2 (2)	C12—C13—C14—C9	−0.5 (4)
C5—C6—C7—O2	6.1 (3)	Cl1—C13—C14—C9	179.98 (18)
C1—C6—C7—N1	7.9 (4)	C10—C9—C14—C13	0.1 (4)
C5—C6—C7—N1	−173.8 (2)	C8—C9—C14—C13	−178.6 (2)
N1—N2—C8—C9	−179.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2i	0.83 (1)	1.76 (1)	2.591 (2)	175 (3)
O3—H3o···N2	0.84 (1)	1.88 (2)	2.632 (3)	149 (3)
N1—H1n···O1	0.87 (1)	1.90 (2)	2.614 (3)	139 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2i	0.83 (1)	1.76 (1)	2.591 (2)	175 (3)
O3—H3o⋯N2	0.84 (1)	1.88 (2)	2.632 (3)	149 (3)
N1—H1n⋯O1	0.87 (1)	1.90 (2)	2.614 (3)	139 (2)

Symmetry code: (i) .