2′-(3,5-Dichloro-2-hydroxy­benzyl­idene)-2-hydroxy­benzohydrazide

The mol­ecule of the title compound, C₁₄H₁₀Cl₂N₂O₃, has a trans configuration with respect to the C=N and C—N bonds. The dihedral angle between the two benzene rings is 2.0 (2)°. In the crystal structure, mol­ecules are linked through O—H...O and weak C—H...O inter­molecular hydrogen bonds, forming chains running along the [001] axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.106
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.

2'-(3,5-Dichloro-2-hydroxybenzylidene)-2-hydroxybenzohydrazide

Crystal data

C14H10Cl2N2O3	F(000) = 664
Mr = 325.14	Dx = 1.517 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1683 reflections
a = 16.003 (2) Å	θ = 2.7–24.3°
b = 7.080 (1) Å	µ = 0.47 mm^−1
c = 13.269 (2) Å	T = 298 K
β = 108.723 (2)°	Block cut from needle, yellow
V = 1423.8 (3) Å^3	0.20 × 0.13 × 0.11 mm
Z = 4

Data collection

Bruker SMART APEX 1K area-detector diffractometer	2625 independent reflections
Radiation source: fine-focus sealed tube	1704 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω scans	θmax = 25.4°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→18
Tmin = 0.913, Tmax = 0.951	k = −8→8
7101 measured reflections	l = −16→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0432P)^2 + 0.3502P] where P = (Fo^2 + 2Fc^2)/3
2625 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.24 e Å^−3
3 restraints	Δρmin = −0.23 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.65209 (5)	0.49775 (13)	0.54632 (5)	0.0941 (3)
Cl2	0.49185 (5)	0.55704 (13)	0.84366 (8)	0.0999 (3)
O1	0.80450 (11)	0.3848 (3)	0.72190 (13)	0.0660 (5)
O2	1.04943 (12)	0.2485 (3)	0.91954 (13)	0.0921 (7)
O3	1.02340 (11)	0.2171 (3)	1.21788 (12)	0.0733 (5)
N1	0.88742 (12)	0.3200 (3)	0.92673 (14)	0.0544 (5)
N2	0.95649 (13)	0.2650 (3)	1.01335 (14)	0.0542 (5)
C1	0.73578 (15)	0.4057 (3)	0.85930 (18)	0.0521 (6)
C2	0.73465 (15)	0.4223 (3)	0.75353 (18)	0.0531 (6)
C3	0.65591 (16)	0.4789 (3)	0.67792 (19)	0.0604 (6)
C4	0.58224 (16)	0.5220 (3)	0.7044 (2)	0.0652 (7)
H4	0.5310	0.5622	0.6525	0.078*
C5	0.58479 (16)	0.5053 (3)	0.8088 (2)	0.0653 (7)
C6	0.66049 (16)	0.4474 (3)	0.8852 (2)	0.0604 (6)
H6	0.6614	0.4358	0.9554	0.072*
C7	0.81436 (15)	0.3471 (3)	0.94349 (18)	0.0561 (6)
H7	0.8113	0.3288	1.0116	0.067*
C8	1.03607 (15)	0.2328 (3)	1.00427 (17)	0.0525 (6)
C9	1.10784 (14)	0.1779 (3)	1.10196 (16)	0.0470 (5)
C10	1.10150 (14)	0.1721 (3)	1.20402 (17)	0.0509 (6)
C11	1.17438 (16)	0.1222 (4)	1.28950 (18)	0.0611 (6)
H11	1.1699	0.1183	1.3576	0.073*
C12	1.25299 (16)	0.0787 (3)	1.27448 (19)	0.0618 (7)
H12	1.3015	0.0460	1.3325	0.074*
C13	1.26046 (15)	0.0830 (3)	1.1741 (2)	0.0608 (6)
H13	1.3137	0.0532	1.1638	0.073*
C14	1.18879 (15)	0.1315 (3)	1.08979 (18)	0.0546 (6)
H14	1.1941	0.1338	1.0220	0.066*
H2	0.9502 (16)	0.258 (4)	1.0779 (11)	0.080*
H3	1.0272 (17)	0.229 (4)	1.2831 (9)	0.080*
H1	0.8484 (11)	0.358 (4)	0.7766 (14)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0814 (5)	0.1379 (7)	0.0495 (4)	−0.0040 (5)	0.0019 (4)	0.0104 (4)
Cl2	0.0652 (5)	0.1179 (7)	0.1200 (7)	0.0130 (4)	0.0343 (5)	0.0044 (5)
O1	0.0588 (11)	0.0825 (12)	0.0523 (10)	0.0014 (9)	0.0119 (8)	0.0034 (9)
O2	0.0739 (12)	0.167 (2)	0.0372 (10)	0.0047 (13)	0.0197 (9)	0.0116 (11)
O3	0.0597 (10)	0.1244 (16)	0.0351 (9)	0.0183 (10)	0.0144 (8)	0.0042 (10)
N1	0.0536 (11)	0.0565 (12)	0.0436 (11)	−0.0013 (9)	0.0020 (9)	0.0025 (9)
N2	0.0539 (11)	0.0674 (13)	0.0353 (10)	0.0023 (10)	0.0061 (9)	0.0030 (10)
C1	0.0535 (13)	0.0482 (14)	0.0490 (13)	−0.0032 (11)	0.0084 (11)	−0.0005 (11)
C2	0.0529 (14)	0.0488 (14)	0.0510 (14)	−0.0053 (11)	0.0075 (12)	−0.0007 (11)
C3	0.0588 (15)	0.0636 (16)	0.0501 (14)	−0.0081 (12)	0.0052 (12)	0.0033 (12)
C4	0.0523 (15)	0.0644 (17)	0.0646 (17)	−0.0034 (12)	−0.0014 (13)	0.0058 (13)
C5	0.0559 (15)	0.0618 (16)	0.0758 (18)	−0.0019 (12)	0.0177 (14)	0.0003 (14)
C6	0.0637 (15)	0.0591 (15)	0.0553 (14)	−0.0018 (12)	0.0147 (13)	0.0003 (12)
C7	0.0616 (15)	0.0570 (15)	0.0432 (13)	−0.0014 (12)	0.0077 (12)	0.0017 (11)
C8	0.0546 (14)	0.0638 (15)	0.0366 (12)	−0.0056 (12)	0.0112 (11)	−0.0002 (11)
C9	0.0510 (13)	0.0494 (13)	0.0395 (12)	−0.0033 (10)	0.0130 (10)	−0.0029 (10)
C10	0.0488 (13)	0.0613 (15)	0.0412 (12)	0.0020 (11)	0.0122 (10)	−0.0023 (11)
C11	0.0631 (15)	0.0759 (17)	0.0401 (13)	0.0065 (13)	0.0107 (12)	0.0046 (12)
C12	0.0544 (14)	0.0665 (17)	0.0549 (15)	0.0067 (12)	0.0039 (12)	0.0039 (12)
C13	0.0511 (14)	0.0653 (16)	0.0665 (17)	0.0013 (12)	0.0195 (13)	−0.0038 (13)
C14	0.0573 (14)	0.0612 (15)	0.0467 (13)	−0.0029 (12)	0.0186 (12)	−0.0040 (12)

Geometric parameters (Å, º)

Cl1—C3	1.733 (3)	C4—C5	1.378 (4)
Cl2—C5	1.733 (3)	C4—H4	0.9300
O1—C2	1.341 (3)	C5—C6	1.369 (3)
O1—H1	0.853 (10)	C6—H6	0.9300
O2—C8	1.215 (2)	C7—H7	0.9300
O3—C10	1.358 (3)	C8—C9	1.482 (3)
O3—H3	0.852 (10)	C9—C10	1.391 (3)
N1—C7	1.273 (3)	C9—C14	1.395 (3)
N1—N2	1.371 (2)	C10—C11	1.386 (3)
N2—C8	1.337 (3)	C11—C12	1.370 (3)
N2—H2	0.895 (10)	C11—H11	0.9300
C1—C6	1.387 (3)	C12—C13	1.375 (3)
C1—C2	1.403 (3)	C12—H12	0.9300
C1—C7	1.449 (3)	C13—C14	1.364 (3)
C2—C3	1.394 (3)	C13—H13	0.9300
C3—C4	1.368 (3)	C14—H14	0.9300
C2—O1—H1	108.6 (17)	N1—C7—C1	121.8 (2)
C10—O3—H3	113.1 (18)	N1—C7—H7	119.1
C7—N1—N2	115.8 (2)	C1—C7—H7	119.1
C8—N2—N1	120.53 (19)	O2—C8—N2	121.6 (2)
C8—N2—H2	118.7 (16)	O2—C8—C9	121.1 (2)
N1—N2—H2	120.7 (16)	N2—C8—C9	117.34 (19)
C6—C1—C2	119.8 (2)	C10—C9—C14	117.8 (2)
C6—C1—C7	118.5 (2)	C10—C9—C8	125.5 (2)
C2—C1—C7	121.6 (2)	C14—C9—C8	116.63 (19)
O1—C2—C3	118.9 (2)	O3—C10—C11	121.2 (2)
O1—C2—C1	123.5 (2)	O3—C10—C9	118.87 (19)
C3—C2—C1	117.5 (2)	C11—C10—C9	119.9 (2)
C4—C3—C2	122.3 (2)	C12—C11—C10	120.6 (2)
C4—C3—Cl1	119.13 (19)	C12—C11—H11	119.7
C2—C3—Cl1	118.6 (2)	C10—C11—H11	119.7
C3—C4—C5	119.3 (2)	C11—C12—C13	120.3 (2)
C3—C4—H4	120.4	C11—C12—H12	119.8
C5—C4—H4	120.4	C13—C12—H12	119.8
C6—C5—C4	120.3 (2)	C14—C13—C12	119.2 (2)
C6—C5—Cl2	119.8 (2)	C14—C13—H13	120.4
C4—C5—Cl2	120.0 (2)	C12—C13—H13	120.4
C5—C6—C1	120.8 (2)	C13—C14—C9	122.1 (2)
C5—C6—H6	119.6	C13—C14—H14	118.9
C1—C6—H6	119.6	C9—C14—H14	118.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.85 (1)	1.91 (2)	2.654 (2)	145 (2)
O3—H3···O2^i	0.85 (1)	1.74 (1)	2.584 (2)	173 (3)
N2—H2···O3	0.90 (1)	1.87 (2)	2.600 (2)	137 (2)
C11—H11···O2^i	0.93	2.51	3.167 (2)	128 (2)
C14—H14···O2	0.93	2.42	2.744 (2)	100

Symmetry code: (i) x, −y+1/2, z+1/2.