3,4-Dichloro­benzaldehyde (2-hydroxybenzo­yl)hydrazone

The mol­ecule of the title compound, C₁₄H₁₀Cl₂N₂O₂, is roughly planar and displays a trans configuration with respect to the C=N double bond. The dihedral angle between the two benzene rings is 14.5 (2)°. The compound adopts a chain structure which is stabilized by inter­molecular O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.039
• wR factor = 0.102
• Data-to-parameter ratio = 10.7

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.

3,4-Dichlorobenzaldehyde (2-hydroxybenzoyl)hydrazone

Crystal data

C14H10Cl2N2O2	F(000) = 632
Mr = 309.14	Dx = 1.536 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2023 reflections
a = 6.0466 (18) Å	θ = 2.8–25.2°
b = 19.314 (6) Å	µ = 0.49 mm^−1
c = 11.452 (3) Å	T = 298 K
β = 91.034 (4)°	Block, colourless
V = 1337.2 (7) Å^3	0.43 × 0.32 × 0.21 mm
Z = 4

Data collection

Bruker SMART APEX area-detector diffractometer	2363 independent reflections
Radiation source: fine-focus sealed tube	1580 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −7→7
Tmin = 0.818, Tmax = 0.905	k = −17→22
6948 measured reflections	l = −13→13

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) = 0.102	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0388P)^2 + 0.6353P] where P = (Fo^2 + 2Fc^2)/3
2363 reflections	(Δ/σ)max = 0.001
221 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.22137 (14)	0.98427 (5)	0.08566 (7)	0.0711 (3)
Cl2	0.10405 (12)	1.01197 (4)	0.34796 (7)	0.0633 (3)
O1	1.2399 (3)	0.71663 (10)	0.43600 (15)	0.0511 (5)
O2	1.4320 (3)	0.73774 (11)	0.08884 (17)	0.0512 (5)
H2	1.493 (5)	0.7465 (17)	0.031 (3)	0.078 (12)*
N1	1.1715 (3)	0.76936 (12)	0.2636 (2)	0.0413 (6)
H1	1.198 (4)	0.7738 (12)	0.197 (2)	0.034 (7)*
N2	0.9930 (3)	0.80481 (11)	0.30581 (18)	0.0404 (5)
C1	1.2895 (4)	0.72702 (13)	0.3333 (2)	0.0384 (6)
C2	1.4858 (4)	0.69291 (12)	0.2819 (2)	0.0353 (6)
C3	1.5540 (4)	0.69969 (13)	0.1665 (2)	0.0388 (6)
C4	1.7469 (5)	0.66753 (15)	0.1314 (3)	0.0480 (7)
H4	1.786 (4)	0.6738 (14)	0.058 (3)	0.059 (9)*
C5	1.8695 (5)	0.62897 (16)	0.2081 (3)	0.0537 (8)
H5	1.999 (5)	0.6092 (15)	0.185 (2)	0.065 (9)*
C6	1.8047 (5)	0.62081 (16)	0.3214 (3)	0.0533 (8)
H6	1.890 (4)	0.5926 (13)	0.372 (2)	0.052 (8)*
C7	1.6152 (5)	0.65276 (15)	0.3566 (2)	0.0472 (7)
H7	1.571 (4)	0.6484 (13)	0.436 (2)	0.047 (7)*
C8	0.8762 (4)	0.83556 (14)	0.2283 (3)	0.0430 (7)
H8	0.906 (4)	0.8327 (13)	0.149 (2)	0.043 (7)*
C9	0.6857 (4)	0.87738 (13)	0.2595 (2)	0.0391 (6)
C10	0.5571 (4)	0.90682 (15)	0.1715 (2)	0.0452 (7)
H10	0.591 (4)	0.8982 (13)	0.094 (3)	0.056 (8)*
C11	0.3775 (4)	0.94783 (14)	0.1977 (2)	0.0443 (7)
C12	0.3237 (4)	0.95973 (13)	0.3122 (2)	0.0432 (7)
C13	0.4513 (5)	0.93022 (14)	0.4008 (3)	0.0478 (7)
H13	0.404 (4)	0.9428 (14)	0.477 (3)	0.061 (8)*
C14	0.6287 (5)	0.88939 (15)	0.3750 (2)	0.0459 (7)
H14	0.716 (4)	0.8675 (13)	0.433 (2)	0.042 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0666 (5)	0.0924 (7)	0.0538 (5)	0.0216 (5)	−0.0131 (4)	0.0012 (4)
Cl2	0.0543 (5)	0.0645 (5)	0.0716 (6)	0.0116 (4)	0.0153 (4)	−0.0034 (4)
O1	0.0530 (12)	0.0675 (13)	0.0332 (11)	0.0078 (10)	0.0124 (9)	0.0037 (9)
O2	0.0530 (12)	0.0672 (14)	0.0339 (11)	0.0141 (10)	0.0172 (10)	0.0080 (10)
N1	0.0394 (13)	0.0534 (15)	0.0314 (13)	0.0044 (11)	0.0123 (11)	0.0017 (11)
N2	0.0359 (12)	0.0456 (13)	0.0400 (13)	−0.0013 (10)	0.0081 (10)	−0.0052 (10)
C1	0.0380 (14)	0.0464 (16)	0.0311 (14)	−0.0071 (12)	0.0059 (11)	−0.0020 (12)
C2	0.0372 (14)	0.0378 (14)	0.0312 (14)	−0.0026 (11)	0.0056 (11)	−0.0042 (11)
C3	0.0406 (15)	0.0390 (15)	0.0370 (15)	−0.0013 (12)	0.0055 (12)	−0.0002 (12)
C4	0.0543 (18)	0.0487 (18)	0.0416 (17)	0.0055 (14)	0.0176 (14)	−0.0019 (14)
C5	0.0487 (18)	0.0524 (19)	0.060 (2)	0.0103 (15)	0.0109 (16)	−0.0040 (15)
C6	0.0528 (19)	0.058 (2)	0.0488 (18)	0.0108 (15)	−0.0017 (15)	0.0047 (15)
C7	0.0503 (17)	0.0553 (18)	0.0361 (16)	0.0016 (14)	0.0052 (13)	0.0008 (13)
C8	0.0431 (16)	0.0502 (17)	0.0359 (16)	−0.0017 (13)	0.0069 (13)	−0.0019 (13)
C9	0.0397 (15)	0.0403 (15)	0.0374 (15)	−0.0044 (12)	0.0032 (12)	−0.0002 (11)
C10	0.0450 (17)	0.0559 (18)	0.0349 (16)	−0.0003 (14)	0.0034 (13)	−0.0031 (13)
C11	0.0410 (15)	0.0494 (17)	0.0424 (16)	−0.0039 (13)	−0.0018 (12)	0.0028 (13)
C12	0.0408 (15)	0.0390 (15)	0.0502 (17)	−0.0041 (12)	0.0097 (13)	−0.0024 (13)
C13	0.0567 (18)	0.0465 (17)	0.0406 (17)	0.0008 (14)	0.0135 (14)	−0.0013 (13)
C14	0.0511 (17)	0.0477 (17)	0.0391 (16)	0.0018 (14)	0.0021 (13)	0.0036 (13)

Geometric parameters (Å, º)

Cl1—C11	1.729 (3)	C5—H5	0.92 (3)
Cl2—C12	1.723 (3)	C6—C7	1.369 (4)
O1—C1	1.236 (3)	C6—H6	0.94 (3)
O2—C3	1.360 (3)	C7—H7	0.95 (3)
O2—H2	0.79 (3)	C8—C9	1.457 (4)
N1—C1	1.339 (3)	C8—H8	0.94 (2)
N1—N2	1.373 (3)	C9—C10	1.384 (4)
N1—H1	0.79 (2)	C9—C14	1.392 (3)
N2—C8	1.272 (3)	C10—C11	1.381 (4)
C1—C2	1.488 (3)	C10—H10	0.93 (3)
C2—C7	1.386 (4)	C11—C12	1.377 (4)
C2—C3	1.398 (3)	C12—C13	1.386 (4)
C3—C4	1.387 (4)	C13—C14	1.368 (4)
C4—C5	1.361 (4)	C13—H13	0.95 (3)
C4—H4	0.89 (3)	C14—H14	0.94 (2)
C5—C6	1.371 (4)
C3—O2—H2	114 (2)	C6—C7—H7	119.3 (15)
C1—N1—N2	120.6 (2)	C2—C7—H7	118.2 (15)
C1—N1—H1	121.9 (18)	N2—C8—C9	121.3 (2)
N2—N1—H1	117.5 (18)	N2—C8—H8	122.7 (15)
C8—N2—N1	114.7 (2)	C9—C8—H8	116.0 (15)
O1—C1—N1	122.0 (2)	C10—C9—C14	118.6 (2)
O1—C1—C2	120.9 (2)	C10—C9—C8	119.0 (2)
N1—C1—C2	117.1 (2)	C14—C9—C8	122.4 (2)
C7—C2—C3	117.6 (2)	C11—C10—C9	120.7 (3)
C7—C2—C1	116.7 (2)	C11—C10—H10	119.9 (17)
C3—C2—C1	125.7 (2)	C9—C10—H10	119.4 (17)
O2—C3—C4	120.1 (2)	C12—C11—C10	120.2 (3)
O2—C3—C2	120.2 (2)	C12—C11—Cl1	120.2 (2)
C4—C3—C2	119.7 (3)	C10—C11—Cl1	119.6 (2)
C5—C4—C3	120.6 (3)	C11—C12—C13	119.4 (2)
C5—C4—H4	122.3 (18)	C11—C12—Cl2	121.4 (2)
C3—C4—H4	117.1 (18)	C13—C12—Cl2	119.2 (2)
C4—C5—C6	120.8 (3)	C14—C13—C12	120.5 (3)
C4—C5—H5	119.8 (18)	C14—C13—H13	126.4 (17)
C6—C5—H5	119.3 (19)	C12—C13—H13	113.1 (17)
C7—C6—C5	118.8 (3)	C13—C14—C9	120.6 (3)
C7—C6—H6	121.8 (16)	C13—C14—H14	122.3 (15)
C5—C6—H6	119.3 (16)	C9—C14—H14	117.0 (15)
C6—C7—C2	122.4 (3)
C1—N1—N2—C8	−170.6 (2)	C1—C2—C7—C6	−177.5 (3)
N2—N1—C1—O1	2.1 (4)	N1—N2—C8—C9	−177.8 (2)
N2—N1—C1—C2	−177.5 (2)	N2—C8—C9—C10	−176.7 (3)
O1—C1—C2—C7	−3.7 (4)	N2—C8—C9—C14	3.9 (4)
N1—C1—C2—C7	175.9 (2)	C14—C9—C10—C11	0.7 (4)
O1—C1—C2—C3	178.5 (2)	C8—C9—C10—C11	−178.8 (2)
N1—C1—C2—C3	−2.0 (4)	C9—C10—C11—C12	−0.2 (4)
C7—C2—C3—O2	179.1 (2)	C9—C10—C11—Cl1	179.6 (2)
C1—C2—C3—O2	−3.0 (4)	C10—C11—C12—C13	0.0 (4)
C7—C2—C3—C4	−0.9 (4)	Cl1—C11—C12—C13	−179.8 (2)
C1—C2—C3—C4	176.9 (2)	C10—C11—C12—Cl2	178.7 (2)
O2—C3—C4—C5	−179.6 (3)	Cl1—C11—C12—Cl2	−1.1 (3)
C2—C3—C4—C5	0.5 (4)	C11—C12—C13—C14	−0.3 (4)
C3—C4—C5—C6	0.3 (5)	Cl2—C12—C13—C14	−179.0 (2)
C4—C5—C6—C7	−0.7 (5)	C12—C13—C14—C9	0.7 (4)
C5—C6—C7—C2	0.2 (5)	C10—C9—C14—C13	−0.9 (4)
C3—C2—C7—C6	0.6 (4)	C8—C9—C14—C13	178.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.79 (3)	1.99 (3)	2.724 (3)	155 (3)
N1—H1···O2	0.79 (2)	2.02 (2)	2.641 (3)	135 (2)

Symmetry code: (i) x+1/2, −y+3/2, z−1/2.