3-Hydro­xy­salicyl­aldehyde benzoyl­hydrazone

The mol­ecules of the title compound, C₁₄H₁₂N₂O₃, are linked via hydrogen bonds into a chain running along the shortest axis of the orthorhombic cell.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.124
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

3-Hydroxysalicylaldehyde benzoylhydrazone

Crystal data

C14H12N2O3	F(000) = 1072
Mr = 256.26	Dx = 1.303 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3480 reflections
a = 10.6030 (6) Å	θ = 2.5–23.8°
b = 9.7780 (6) Å	µ = 0.09 mm^−1
c = 25.203 (2) Å	T = 295 K
V = 2612.9 (3) Å^3	Prism, yellow
Z = 8	0.39 × 0.31 × 0.20 mm

Data collection

Bruker SMART area-detector diffractometer	1651 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 27.0°, θmin = 2.5°
φ and ω scans	h = −13→13
14751 measured reflections	k = −12→12
2855 independent reflections	l = −32→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0597P)^2 + 0.3349P] where P = (Fo^2 + 2Fc^2)/3
2855 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.14 e Å^−3
3 restraints	Δρmin = −0.15 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.5061 (2)	0.5996 (2)	0.41965 (6)	0.0889 (5)
O2	0.5801 (1)	0.6342 (1)	0.52152 (5)	0.0649 (4)
O3	0.7187 (1)	0.5826 (1)	0.65676 (5)	0.0668 (4)
N1	0.6971 (1)	0.7855 (1)	0.58850 (5)	0.0524 (4)
N2	0.7490 (2)	0.8044 (1)	0.63790 (5)	0.0520 (4)
C1	0.5928 (2)	0.7422 (2)	0.48773 (6)	0.0532 (4)
C2	0.5534 (2)	0.7225 (2)	0.43570 (7)	0.0646 (5)
C3	0.5631 (2)	0.8273 (2)	0.39990 (8)	0.0796 (6)
C4	0.6112 (2)	0.9521 (2)	0.41513 (8)	0.0817 (6)
C5	0.6519 (2)	0.9720 (2)	0.46615 (7)	0.0705 (5)
C6	0.6443 (2)	0.8667 (2)	0.50329 (6)	0.0540 (4)
C7	0.6936 (2)	0.8862 (2)	0.55645 (6)	0.0556 (4)
C8	0.7599 (2)	0.6950 (2)	0.66983 (6)	0.0497 (4)
C9	0.8237 (2)	0.7178 (2)	0.72173 (6)	0.0504 (4)
C10	0.9097 (2)	0.8210 (2)	0.73034 (7)	0.0626 (5)
C11	0.9679 (2)	0.8325 (2)	0.77915 (8)	0.0793 (6)
C12	0.9412 (2)	0.7426 (3)	0.81879 (8)	0.0830 (6)
C13	0.8572 (2)	0.6397 (3)	0.81063 (8)	0.0874 (7)
C14	0.7984 (2)	0.6268 (2)	0.76232 (7)	0.0739 (6)
H1o	0.509 (3)	0.542 (2)	0.4454 (9)	0.16 (1)*
H2o	0.614 (2)	0.663 (2)	0.5502 (6)	0.10 (1)*
H2n	0.771 (2)	0.886 (1)	0.6468 (7)	0.07 (1)*
H3	0.5370	0.8141	0.3650	0.096*
H4	0.6162	1.0231	0.3907	0.098*
H5	0.6847	1.0564	0.4761	0.085*
H7	0.7225	0.9718	0.5671	0.067*
H10	0.9285	0.8827	0.7034	0.075*
H11	1.0258	0.9023	0.7850	0.095*
H12	0.9806	0.7515	0.8516	0.100*
H13	0.8395	0.5781	0.8377	0.105*
H14	0.7411	0.5561	0.7569	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.118 (1)	0.088 (1)	0.061 (1)	−0.027 (1)	−0.026 (1)	−0.003 (1)
O2	0.092 (1)	0.052 (1)	0.050 (1)	−0.011 (1)	−0.012 (1)	0.003 (1)
O3	0.108 (1)	0.036 (1)	0.057 (1)	−0.006 (1)	−0.006 (1)	−0.005 (1)
N1	0.070 (1)	0.046 (1)	0.041 (1)	−0.004 (1)	−0.004 (1)	−0.001 (1)
N2	0.079 (1)	0.036 (1)	0.041 (1)	−0.006 (1)	−0.006 (1)	−0.003 (1)
C1	0.058 (1)	0.056 (1)	0.046 (1)	0.001 (1)	−0.003 (1)	0.003 (1)
C2	0.068 (1)	0.073 (1)	0.053 (1)	−0.009 (1)	−0.011 (1)	0.002 (1)
C3	0.088 (2)	0.098 (2)	0.053 (1)	−0.015 (1)	−0.018 (1)	0.014 (1)
C4	0.094 (2)	0.089 (2)	0.062 (1)	−0.013 (1)	−0.014 (1)	0.032 (1)
C5	0.085 (1)	0.064 (1)	0.063 (1)	−0.010 (1)	−0.009 (1)	0.017 (1)
C6	0.060 (1)	0.054 (1)	0.048 (1)	0.003 (1)	−0.002 (1)	0.006 (1)
C7	0.072 (1)	0.044 (1)	0.051 (1)	−0.005 (1)	−0.001 (1)	0.000 (1)
C8	0.068 (1)	0.036 (1)	0.045 (1)	0.002 (1)	0.003 (1)	−0.005 (1)
C9	0.065 (1)	0.042 (1)	0.044 (1)	0.009 (1)	0.003 (1)	−0.005 (1)
C10	0.073 (1)	0.055 (1)	0.060 (1)	0.001 (1)	−0.008 (1)	−0.001 (1)
C11	0.082 (2)	0.080 (1)	0.076 (1)	−0.003 (1)	−0.022 (1)	−0.008 (1)
C12	0.087 (2)	0.109 (2)	0.053 (1)	0.014 (1)	−0.017 (1)	−0.006 (1)
C13	0.101 (2)	0.111 (2)	0.050 (1)	−0.005 (2)	−0.005 (1)	0.016 (1)
C14	0.092 (2)	0.075 (1)	0.055 (1)	−0.011 (1)	−0.004 (1)	0.010 (1)

Geometric parameters (Å, º)

O1—C2	1.363 (2)	C10—C11	1.381 (3)
O2—C1	1.363 (2)	C11—C12	1.361 (3)
O3—C8	1.227 (2)	C12—C13	1.359 (3)
N1—C7	1.275 (2)	C13—C14	1.374 (3)
N1—N2	1.374 (2)	O1—H1o	0.86 (1)
N2—C8	1.344 (2)	O2—H2o	0.86 (1)
C1—C2	1.390 (2)	N2—H2n	0.86 (1)
C1—C6	1.391 (2)	C3—H3	0.93
C2—C3	1.369 (3)	C4—H4	0.93
C3—C4	1.377 (3)	C5—H5	0.93
C4—C5	1.370 (3)	C7—H7	0.93
C5—C6	1.394 (2)	C10—H10	0.93
C6—C7	1.451 (2)	C11—H11	0.93
C8—C9	1.489 (2)	C12—H12	0.93
C9—C10	1.377 (2)	C13—H13	0.93
C9—C14	1.382 (2)	C14—H14	0.93
C7—N1—N2	118.8 (1)	C12—C13—C14	120.0 (2)
C8—N2—N1	118.0 (1)	C13—C14—C9	120.6 (2)
O2—C1—C2	116.9 (2)	C2—O1—H1o	110 (2)
O2—C1—C6	122.7 (1)	C1—O2—H2o	103 (2)
C2—C1—C6	120.4 (2)	C8—N2—H2n	124 (1)
O1—C2—C3	119.4 (2)	N1—N2—H2n	118 (1)
O1—C2—C1	120.9 (2)	C2—C3—H3	119.8
C3—C2—C1	119.7 (2)	C4—C3—H3	119.8
C2—C3—C4	120.5 (2)	C5—C4—H4	119.9
C5—C4—C3	120.3 (2)	C3—C4—H4	119.9
C4—C5—C6	120.5 (2)	C4—C5—H5	119.8
C1—C6—C5	118.7 (2)	C6—C5—H5	119.8
C1—C6—C7	121.1 (1)	N1—C7—H7	120.2
C5—C6—C7	120.2 (2)	C6—C7—H7	120.2
N1—C7—C6	119.6 (2)	C9—C10—H10	120.1
O3—C8—N2	121.4 (2)	C11—C10—H10	120.1
O3—C8—C9	122.1 (1)	C12—C11—H11	119.7
N2—C8—C9	116.5 (1)	C10—C11—H11	119.7
C10—C9—C14	118.9 (2)	C13—C12—H12	119.9
C10—C9—C8	123.3 (2)	C11—C12—H12	119.9
C14—C9—C8	117.7 (2)	C12—C13—H13	120.0
C9—C10—C11	119.7 (2)	C14—C13—H13	120.0
C12—C11—C10	120.6 (2)	C13—C14—H14	119.7
C13—C12—C11	120.24 (19)	C9—C14—H14	119.7
C7—N1—N2—C8	−175.5 (2)	C1—C6—C7—N1	4.4 (3)
O2—C1—C2—O1	−0.9 (3)	C5—C6—C7—N1	−173.4 (2)
C6—C1—C2—O1	178.1 (2)	N1—N2—C8—O3	−3.9 (3)
O2—C1—C2—C3	179.7 (2)	N1—N2—C8—C9	176.4 (1)
C6—C1—C2—C3	−1.3 (3)	O3—C8—C9—C10	155.1 (2)
O1—C2—C3—C4	−179.7 (2)	N2—C8—C9—C10	−25.2 (2)
C1—C2—C3—C4	−0.2 (3)	O3—C8—C9—C14	−22.2 (2)
C2—C3—C4—C5	1.0 (3)	N2—C8—C9—C14	157.5 (2)
C3—C4—C5—C6	−0.4 (3)	C14—C9—C10—C11	−0.6 (3)
O2—C1—C6—C5	−179.1 (2)	C8—C9—C10—C11	−177.8 (2)
C2—C1—C6—C5	2.0 (3)	C9—C10—C11—C12	0.1 (3)
O2—C1—C6—C7	3.0 (3)	C10—C11—C12—C13	0.3 (3)
C2—C1—C6—C7	−175.9 (2)	C11—C12—C13—C14	−0.3 (4)
C4—C5—C6—C1	−1.1 (3)	C12—C13—C14—C9	−0.1 (3)
C4—C5—C6—C7	176.7 (2)	C10—C9—C14—C13	0.6 (3)
N2—N1—C7—C6	177.3 (2)	C8—C9—C14—C13	178.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2	0.86 (1)	2.25 (3)	2.706 (2)	113 (2)
O1—H1o···O2^i	0.86 (1)	2.14 (2)	2.874 (2)	144 (3)
O2—H2o···N1	0.86 (1)	1.77 (1)	2.564 (2)	153 (2)
N2—H2n···O3^ii	0.86 (1)	1.94 (1)	2.783 (2)	165 (2)

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