4-Chloro-N'-(5-chloro-2-hydroxy-benzyl-idene)benzohydrazide.

The mol-ecule of the title compound, C(14)H(10)Cl(2)N(2)O(2), displays a trans configuration with respect to the C=N double bond and has an intramolecular O-H⋯N hydrogen bond. The dihedral angle between the two benzene rings is 1.4 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains running along the a direction.

Related literature

For related structures, see Yang (2006a ▶,b ▶,c ▶,d ▶,e ▶, 2007a ▶,b ▶,c ▶); Yang & Guo (2006 ▶). For related literature, see: Allen et al. (1987 ▶); Bernardo et al. (1996 ▶); Musie et al. (2001 ▶); Paul et al. (2002 ▶).

Experimental

Crystal data

C14H10Cl2N2O2

M = 309.14

Monoclinic,

a = 5.921 (2) Å

b = 31.245 (3) Å

c = 7.428 (3) Å

β = 92.182 (6)°

V = 1373.2 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.47 mm−1

T = 298 (2) K

0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.911, T max = 0.924

6465 measured reflections

2239 independent reflections

1790 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.03

2239 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025816/om2256sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025816/om2256Isup2.hkl

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

C14H10Cl2N2O2	F000 = 632
Mr = 309.14	Dx = 1.495 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2553 reflections
a = 5.921 (2) Å	θ = 2.5–24.3º
b = 31.245 (3) Å	µ = 0.47 mm−1
c = 7.428 (3) Å	T = 298 (2) K
β = 92.182 (6)º	Block, colourless
V = 1373.2 (7) Å3	0.20 × 0.18 × 0.17 mm
Z = 4

Bruker SMART CCD diffractometer	2239 independent reflections
Radiation source: fine-focus sealed tube	1790 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
T = 298(2) K	θmax = 24.4º
ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.911, Tmax = 0.924	k = −36→35
6465 measured reflections	l = −8→6

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0381P)2 + 0.5294P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2239 reflections	Δρmax = 0.25 e Å−3
185 parameters	Δρmin = −0.25 e Å−3
1 restraint	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
Cl1	0.76783 (16)	0.49243 (2)	0.80632 (14)	0.1068 (3)
Cl2	1.33065 (12)	0.06887 (2)	0.76621 (10)	0.0742 (2)
N1	0.6688 (3)	0.29434 (6)	0.6801 (2)	0.0488 (4)
N2	0.8017 (3)	0.25847 (6)	0.7096 (2)	0.0523 (5)
O1	0.2928 (3)	0.33583 (5)	0.5861 (2)	0.0657 (5)
H1	0.3721	0.3146	0.6045	0.099*
O2	0.6020 (3)	0.22073 (5)	0.5012 (2)	0.0640 (5)
C1	0.6271 (3)	0.36918 (6)	0.7166 (3)	0.0445 (5)
C2	0.4080 (4)	0.37128 (7)	0.6396 (3)	0.0504 (5)
C3	0.3035 (4)	0.41076 (9)	0.6172 (3)	0.0665 (7)
H3	0.1576	0.4121	0.5666	0.080*
C4	0.4116 (5)	0.44766 (9)	0.6685 (4)	0.0729 (7)
H4	0.3401	0.4740	0.6522	0.087*
C5	0.6271 (4)	0.44569 (7)	0.7444 (3)	0.0630 (6)
C6	0.7329 (4)	0.40713 (7)	0.7690 (3)	0.0528 (5)
H6	0.8779	0.4063	0.8217	0.063*
C7	0.7485 (4)	0.32942 (7)	0.7410 (3)	0.0468 (5)
H7	0.8882	0.3295	0.8027	0.056*
C8	0.7583 (3)	0.22285 (6)	0.6132 (3)	0.0449 (5)
C9	0.9091 (3)	0.18574 (6)	0.6525 (2)	0.0424 (5)
C10	0.8262 (4)	0.14516 (7)	0.6112 (3)	0.0481 (5)
H10	0.6823	0.1423	0.5578	0.058*
C11	0.9534 (4)	0.10922 (7)	0.6479 (3)	0.0521 (5)
H11	0.8958	0.0821	0.6218	0.062*
C12	1.1670 (4)	0.11401 (7)	0.7236 (3)	0.0489 (5)
C13	1.2546 (4)	0.15368 (7)	0.7646 (3)	0.0509 (5)
H13	1.3993	0.1563	0.8166	0.061*
C14	1.1252 (3)	0.18949 (7)	0.7278 (3)	0.0479 (5)
H14	1.1840	0.2165	0.7538	0.058*
H2	0.913 (3)	0.2592 (8)	0.795 (3)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.1184 (7)	0.0481 (4)	0.1535 (8)	−0.0066 (4)	−0.0009 (6)	0.0049 (4)
Cl2	0.0782 (5)	0.0561 (4)	0.0877 (5)	0.0189 (3)	−0.0070 (4)	−0.0040 (3)
N1	0.0507 (10)	0.0480 (10)	0.0466 (10)	0.0072 (8)	−0.0104 (8)	−0.0010 (8)
N2	0.0576 (12)	0.0464 (10)	0.0512 (11)	0.0081 (9)	−0.0192 (9)	−0.0064 (8)
O1	0.0508 (9)	0.0777 (11)	0.0674 (11)	0.0052 (8)	−0.0123 (8)	−0.0069 (9)
O2	0.0722 (11)	0.0528 (9)	0.0641 (10)	−0.0025 (8)	−0.0340 (9)	−0.0001 (7)
C1	0.0462 (12)	0.0511 (12)	0.0361 (11)	0.0060 (10)	0.0015 (9)	0.0039 (9)
C2	0.0474 (13)	0.0632 (14)	0.0404 (12)	0.0063 (11)	0.0003 (10)	0.0007 (10)
C3	0.0538 (14)	0.0839 (18)	0.0615 (15)	0.0244 (14)	−0.0019 (12)	0.0091 (13)
C4	0.0797 (19)	0.0607 (16)	0.0786 (18)	0.0257 (14)	0.0077 (15)	0.0111 (13)
C5	0.0711 (17)	0.0483 (13)	0.0699 (16)	0.0049 (12)	0.0069 (13)	0.0087 (11)
C6	0.0535 (13)	0.0513 (13)	0.0536 (13)	0.0026 (11)	0.0015 (10)	0.0051 (10)
C7	0.0451 (11)	0.0509 (13)	0.0439 (12)	0.0045 (10)	−0.0065 (9)	0.0019 (9)
C8	0.0491 (12)	0.0444 (11)	0.0406 (11)	−0.0043 (10)	−0.0066 (10)	0.0022 (9)
C9	0.0468 (12)	0.0454 (11)	0.0346 (10)	−0.0013 (9)	−0.0019 (9)	−0.0023 (8)
C10	0.0471 (12)	0.0512 (12)	0.0455 (12)	−0.0030 (10)	−0.0042 (9)	−0.0049 (10)
C11	0.0595 (14)	0.0447 (12)	0.0520 (13)	−0.0051 (11)	0.0036 (11)	−0.0055 (10)
C12	0.0548 (13)	0.0477 (12)	0.0446 (12)	0.0083 (10)	0.0063 (10)	−0.0021 (9)
C13	0.0450 (12)	0.0576 (14)	0.0499 (13)	0.0044 (10)	−0.0023 (10)	−0.0070 (10)
C14	0.0485 (12)	0.0460 (12)	0.0491 (12)	−0.0026 (10)	−0.0014 (10)	−0.0066 (9)

Cl1—C5	1.735 (3)	C4—H4	0.9300
Cl2—C12	1.734 (2)	C5—C6	1.367 (3)
N1—C7	1.270 (3)	C6—H6	0.9300
N1—N2	1.382 (2)	C7—H7	0.9300
N2—C8	1.343 (3)	C8—C9	1.486 (3)
N2—H2	0.898 (10)	C9—C14	1.382 (3)
O1—C2	1.352 (3)	C9—C10	1.390 (3)
O1—H1	0.8200	C10—C11	1.374 (3)
O2—C8	1.222 (2)	C10—H10	0.9300
C1—C6	1.390 (3)	C11—C12	1.373 (3)
C1—C2	1.399 (3)	C11—H11	0.9300
C1—C7	1.443 (3)	C12—C13	1.373 (3)
C2—C3	1.387 (3)	C13—C14	1.377 (3)
C3—C4	1.366 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.376 (4)
C7—N1—N2	116.23 (17)	N1—C7—H7	119.3
C8—N2—N1	119.42 (17)	C1—C7—H7	119.3
C8—N2—H2	121.1 (16)	O2—C8—N2	122.17 (19)
N1—N2—H2	119.4 (16)	O2—C8—C9	121.69 (18)
C2—O1—H1	109.5	N2—C8—C9	116.13 (17)
C6—C1—C2	118.39 (19)	C14—C9—C10	118.74 (19)
C6—C1—C7	118.83 (19)	C14—C9—C8	123.63 (18)
C2—C1—C7	122.77 (19)	C10—C9—C8	117.63 (18)
O1—C2—C3	118.4 (2)	C11—C10—C9	121.0 (2)
O1—C2—C1	122.06 (19)	C11—C10—H10	119.5
C3—C2—C1	119.5 (2)	C9—C10—H10	119.5
C4—C3—C2	121.0 (2)	C12—C11—C10	118.8 (2)
C4—C3—H3	119.5	C12—C11—H11	120.6
C2—C3—H3	119.5	C10—C11—H11	120.6
C3—C4—C5	119.6 (2)	C11—C12—C13	121.6 (2)
C3—C4—H4	120.2	C11—C12—Cl2	119.07 (17)
C5—C4—H4	120.2	C13—C12—Cl2	119.34 (18)
C6—C5—C4	120.5 (2)	C12—C13—C14	119.1 (2)
C6—C5—Cl1	119.6 (2)	C12—C13—H13	120.4
C4—C5—Cl1	119.96 (19)	C14—C13—H13	120.4
C5—C6—C1	121.0 (2)	C13—C14—C9	120.7 (2)
C5—C6—H6	119.5	C13—C14—H14	119.6
C1—C6—H6	119.5	C9—C14—H14	119.6
N1—C7—C1	121.45 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.898 (10)	1.965 (13)	2.826 (2)	160 (2)
O1—H1···N1	0.82	1.93	2.647 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.898 (10)	1.965 (13)	2.826 (2)	160 (2)
O1—H1⋯N1	0.82	1.93	2.647 (2)	145

Symmetry code: (i) .