organic compounds
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—HO and weak C—HO intermolecular hydrogen bonds, forming chains running along the [001] axis.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014195/bh2089sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014195/bh2089Isup2.hkl |
CCDC reference: 646722
Computing details top
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 top
Crystal data top
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) Å3 | 0.20 × 0.13 × 0.11 mm |
Z = 4 |
Data collection top
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 top
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0432P)2 + 0.3502P] where P = (Fo2 + 2Fc2)/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 (Å2) top
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 (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
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) top
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) top
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···O2i | 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···O2i | 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. |