N′-[(1E)-(5-Chloro-2-hydroxy­phen­yl)(phen­yl)methyl­ene]-2-hydroxy­benzohydrazide

The title compound, C₂₀H₁₅ClN₂O₃, displays a trans configuration with respect to the C=N double bond. The crystal structure is stabilized by intra­molecular O—H...N and N—H...O and inter­molecular O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.115
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.

N'-[(1E)-(5-Chloro-2-hydroxyphenyl)(phenyl)methylene]-2-hydroxybenzohydrazide

Crystal data

C20H15ClN2O3	F(000) = 1520
Mr = 366.79	Dx = 1.318 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5275 reflections
a = 15.3237 (6) Å	θ = 2.4–21.5°
b = 12.0171 (5) Å	µ = 0.23 mm^−1
c = 20.0773 (8) Å	T = 273 K
V = 3697.2 (3) Å^3	Block, colourless
Z = 8	0.45 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3248 independent reflections
Radiation source: fine-focus sealed tube	2261 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→15
Tmin = 0.924, Tmax = 0.978	k = −14→14
39233 measured reflections	l = −23→23

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) = 0.115	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0507P)^2 + 1.2845P] where P = (Fo^2 + 2Fc^2)/3
3248 reflections	(Δ/σ)max = 0.001
237 parameters	Δρmax = 0.12 e Å^−3
18 restraints	Δρmin = −0.22 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	1.09963 (5)	0.85633 (6)	0.30089 (4)	0.0975 (3)
O1	0.99237 (12)	1.16483 (12)	0.09131 (8)	0.0717 (5)
H1	0.9591	1.1359	0.0644	0.107*
O2	0.84619 (9)	1.14393 (11)	−0.05196 (7)	0.0563 (4)
O3	0.73116 (14)	0.83443 (13)	−0.05047 (9)	0.0882 (6)
H3	0.7039	0.7763	−0.0555	0.132*
N1	0.90070 (10)	1.00781 (13)	0.04214 (8)	0.0498 (4)
N2	0.84440 (10)	0.97365 (13)	−0.00650 (8)	0.0499 (4)
H2	0.8267	0.9058	−0.0080	0.060*
C1	1.01537 (14)	1.08944 (17)	0.13786 (10)	0.0539 (5)
C2	0.98516 (12)	0.97898 (15)	0.13790 (9)	0.0454 (5)
C3	1.01305 (13)	0.90851 (17)	0.18889 (9)	0.0507 (5)
H3A	0.9939	0.8351	0.1898	0.061*
C4	1.06837 (14)	0.94629 (19)	0.23773 (10)	0.0594 (6)
C5	1.09790 (15)	1.0544 (2)	0.23730 (11)	0.0680 (6)
H5	1.1353	1.0794	0.2706	0.082*
C6	1.07182 (15)	1.12493 (19)	0.18764 (11)	0.0652 (6)
H6	1.0922	1.1978	0.1872	0.078*
C7	0.92515 (12)	0.93681 (16)	0.08668 (9)	0.0450 (5)
C8	0.89440 (13)	0.81937 (16)	0.08701 (9)	0.0480 (5)
C9	0.81224 (15)	0.7930 (2)	0.10964 (12)	0.0711 (7)
H9	0.7767	0.8487	0.1270	0.085*
C10	0.78195 (19)	0.6851 (3)	0.10696 (16)	0.0918 (9)
H10	0.7264	0.6682	0.1226	0.110*
C11	0.8329 (2)	0.6040 (3)	0.08172 (15)	0.0930 (10)
H11	0.8119	0.5316	0.0791	0.112*
C12	0.9149 (2)	0.6275 (2)	0.06003 (15)	0.0971 (9)
H12	0.9502	0.5708	0.0437	0.116*
C13	0.94613 (17)	0.73602 (19)	0.06226 (12)	0.0720 (7)
H13	1.0020	0.7521	0.0470	0.086*
C14	0.81715 (13)	1.04834 (16)	−0.05220 (9)	0.0459 (5)
C15	0.75267 (13)	1.00895 (15)	−0.10192 (9)	0.0469 (5)
C16	0.71261 (14)	0.90519 (16)	−0.10126 (10)	0.0557 (5)
C17	0.65505 (15)	0.87517 (19)	−0.15125 (12)	0.0679 (6)
H17	0.6283	0.8057	−0.1501	0.081*
C18	0.63731 (17)	0.9473 (2)	−0.20245 (13)	0.0760 (7)
H18	0.5992	0.9265	−0.2362	0.091*
C19	0.67607 (17)	1.0507 (2)	−0.20376 (12)	0.0774 (7)
H19	0.6639	1.0999	−0.2383	0.093*
C20	0.73247 (15)	1.08075 (18)	−0.15421 (11)	0.0618 (6)
H20	0.7580	1.1509	−0.1554	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1156 (6)	0.0982 (5)	0.0785 (4)	−0.0081 (4)	−0.0450 (4)	0.0153 (4)
O1	0.0962 (13)	0.0509 (9)	0.0678 (10)	−0.0081 (8)	−0.0100 (9)	0.0031 (7)
O2	0.0619 (9)	0.0383 (8)	0.0687 (9)	−0.0007 (7)	−0.0037 (7)	0.0050 (7)
O3	0.1195 (15)	0.0561 (10)	0.0892 (12)	−0.0323 (10)	−0.0494 (11)	0.0311 (9)
N1	0.0549 (10)	0.0469 (9)	0.0477 (9)	0.0039 (8)	−0.0059 (8)	−0.0017 (8)
N2	0.0611 (11)	0.0395 (9)	0.0489 (9)	0.0002 (8)	−0.0100 (8)	0.0041 (7)
C1	0.0581 (13)	0.0521 (12)	0.0516 (11)	0.0004 (10)	0.0041 (10)	−0.0041 (10)
C2	0.0454 (11)	0.0472 (11)	0.0437 (10)	0.0018 (9)	0.0032 (8)	−0.0048 (8)
C3	0.0505 (12)	0.0526 (12)	0.0489 (11)	0.0009 (9)	−0.0011 (9)	−0.0024 (9)
C4	0.0580 (13)	0.0680 (14)	0.0524 (12)	0.0014 (11)	−0.0078 (10)	−0.0006 (10)
C5	0.0621 (14)	0.0797 (17)	0.0623 (14)	−0.0082 (13)	−0.0109 (11)	−0.0142 (12)
C6	0.0667 (15)	0.0588 (14)	0.0702 (15)	−0.0129 (12)	−0.0018 (12)	−0.0102 (12)
C7	0.0457 (11)	0.0472 (11)	0.0420 (10)	0.0038 (9)	0.0027 (8)	−0.0009 (9)
C8	0.0520 (12)	0.0492 (11)	0.0427 (10)	−0.0048 (10)	−0.0077 (9)	0.0051 (9)
C9	0.0573 (14)	0.0747 (16)	0.0813 (16)	−0.0043 (12)	−0.0002 (12)	0.0209 (13)
C10	0.0752 (19)	0.093 (2)	0.108 (2)	−0.0310 (17)	−0.0207 (16)	0.0407 (18)
C11	0.122 (3)	0.0671 (18)	0.090 (2)	−0.0374 (19)	−0.0407 (19)	0.0199 (15)
C12	0.137 (3)	0.0545 (16)	0.100 (2)	−0.0027 (18)	0.003 (2)	−0.0095 (14)
C13	0.0831 (17)	0.0519 (14)	0.0809 (16)	0.0000 (13)	0.0091 (13)	−0.0044 (12)
C14	0.0502 (11)	0.0412 (11)	0.0463 (10)	0.0058 (9)	0.0046 (9)	0.0040 (9)
C15	0.0500 (11)	0.0411 (10)	0.0496 (10)	0.0049 (9)	−0.0016 (9)	0.0069 (8)
C16	0.0622 (13)	0.0467 (12)	0.0581 (12)	0.0010 (10)	−0.0113 (10)	0.0113 (10)
C17	0.0698 (15)	0.0543 (13)	0.0795 (16)	−0.0054 (11)	−0.0225 (13)	0.0075 (12)
C18	0.0770 (17)	0.0739 (17)	0.0770 (16)	0.0018 (14)	−0.0308 (13)	0.0067 (13)
C19	0.0882 (18)	0.0726 (17)	0.0715 (15)	0.0029 (14)	−0.0248 (14)	0.0220 (13)
C20	0.0673 (14)	0.0525 (13)	0.0656 (13)	0.0012 (11)	−0.0100 (11)	0.0129 (10)

Geometric parameters (Å, º)

Cl1—C4	1.734 (2)	C8—C9	1.375 (3)
O1—C1	1.349 (2)	C9—C10	1.379 (4)
O1—H1	0.8200	C9—H9	0.9300
O2—C14	1.232 (2)	C10—C11	1.347 (4)
O3—C16	1.358 (2)	C10—H10	0.9300
O3—H3	0.8200	C11—C12	1.360 (4)
N1—C7	1.292 (2)	C11—H11	0.9300
N1—N2	1.366 (2)	C12—C13	1.390 (4)
N2—C14	1.350 (2)	C12—H12	0.9300
N2—H2	0.8600	C13—H13	0.9300
C1—C6	1.389 (3)	C14—C15	1.482 (3)
C1—C2	1.406 (3)	C15—C16	1.390 (3)
C2—C3	1.396 (3)	C15—C20	1.394 (3)
C2—C7	1.470 (3)	C16—C17	1.384 (3)
C3—C4	1.373 (3)	C17—C18	1.372 (3)
C3—H3A	0.9300	C17—H17	0.9300
C4—C5	1.376 (3)	C18—C19	1.377 (3)
C5—C6	1.368 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.366 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.488 (3)	C20—H20	0.9300
C8—C13	1.371 (3)
C1—O1—H1	109.5	C11—C10—C9	120.0 (3)
C16—O3—H3	109.5	C11—C10—H10	120.0
C7—N1—N2	118.66 (16)	C9—C10—H10	120.0
C14—N2—N1	118.78 (16)	C10—C11—C12	120.4 (3)
C14—N2—H2	120.6	C10—C11—H11	119.8
N1—N2—H2	120.6	C12—C11—H11	119.8
O1—C1—C6	117.08 (19)	C11—C12—C13	120.2 (3)
O1—C1—C2	123.27 (18)	C11—C12—H12	119.9
C6—C1—C2	119.6 (2)	C13—C12—H12	119.9
C3—C2—C1	118.19 (18)	C8—C13—C12	119.9 (3)
C3—C2—C7	119.71 (17)	C8—C13—H13	120.1
C1—C2—C7	122.09 (17)	C12—C13—H13	120.1
C4—C3—C2	120.80 (19)	O2—C14—N2	120.37 (18)
C4—C3—H3A	119.6	O2—C14—C15	122.77 (17)
C2—C3—H3A	119.6	N2—C14—C15	116.85 (17)
C3—C4—C5	120.7 (2)	C16—C15—C20	117.68 (18)
C3—C4—Cl1	119.11 (17)	C16—C15—C14	125.06 (17)
C5—C4—Cl1	120.16 (17)	C20—C15—C14	117.24 (18)
C6—C5—C4	119.6 (2)	O3—C16—C17	120.98 (19)
C6—C5—H5	120.2	O3—C16—C15	118.46 (18)
C4—C5—H5	120.2	C17—C16—C15	120.56 (18)
C5—C6—C1	121.1 (2)	C18—C17—C16	120.3 (2)
C5—C6—H6	119.5	C18—C17—H17	119.8
C1—C6—H6	119.5	C16—C17—H17	119.8
N1—C7—C2	115.99 (17)	C17—C18—C19	119.9 (2)
N1—C7—C8	122.53 (17)	C17—C18—H18	120.0
C2—C7—C8	121.48 (16)	C19—C18—H18	120.0
C13—C8—C9	118.8 (2)	C20—C19—C18	119.8 (2)
C13—C8—C7	120.56 (19)	C20—C19—H19	120.1
C9—C8—C7	120.64 (19)	C18—C19—H19	120.1
C8—C9—C10	120.8 (3)	C19—C20—C15	121.7 (2)
C8—C9—H9	119.6	C19—C20—H20	119.2
C10—C9—H9	119.6	C15—C20—H20	119.2
C7—N1—N2—C14	178.47 (17)	C7—C8—C9—C10	176.8 (2)
O1—C1—C2—C3	−179.66 (19)	C8—C9—C10—C11	−0.3 (4)
C6—C1—C2—C3	0.4 (3)	C9—C10—C11—C12	1.3 (4)
O1—C1—C2—C7	−0.2 (3)	C10—C11—C12—C13	−1.5 (4)
C6—C1—C2—C7	179.79 (18)	C9—C8—C13—C12	0.4 (3)
C1—C2—C3—C4	0.1 (3)	C7—C8—C13—C12	−177.0 (2)
C7—C2—C3—C4	−179.30 (18)	C11—C12—C13—C8	0.6 (4)
C2—C3—C4—C5	−0.3 (3)	N1—N2—C14—O2	3.8 (3)
C2—C3—C4—Cl1	178.83 (15)	N1—N2—C14—C15	−176.99 (16)
C3—C4—C5—C6	0.0 (4)	O2—C14—C15—C16	−174.5 (2)
Cl1—C4—C5—C6	−179.15 (18)	N2—C14—C15—C16	6.3 (3)
C4—C5—C6—C1	0.5 (4)	O2—C14—C15—C20	7.1 (3)
O1—C1—C6—C5	179.3 (2)	N2—C14—C15—C20	−172.09 (18)
C2—C1—C6—C5	−0.7 (3)	C20—C15—C16—O3	−179.6 (2)
N2—N1—C7—C2	−179.53 (15)	C14—C15—C16—O3	2.0 (3)
N2—N1—C7—C8	0.0 (3)	C20—C15—C16—C17	0.3 (3)
C3—C2—C7—N1	178.37 (17)	C14—C15—C16—C17	−178.1 (2)
C1—C2—C7—N1	−1.0 (3)	O3—C16—C17—C18	−179.6 (2)
C3—C2—C7—C8	−1.2 (3)	C15—C16—C17—C18	0.5 (4)
C1—C2—C7—C8	179.41 (18)	C16—C17—C18—C19	−0.8 (4)
N1—C7—C8—C13	100.0 (2)	C17—C18—C19—C20	0.4 (4)
C2—C7—C8—C13	−80.5 (2)	C18—C19—C20—C15	0.4 (4)
N1—C7—C8—C9	−77.3 (3)	C16—C15—C20—C19	−0.7 (3)
C2—C7—C8—C9	102.2 (2)	C14—C15—C20—C19	177.8 (2)
C13—C8—C9—C10	−0.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.84	2.551 (1)	145
N2—H2···O3	0.86	1.90	2.567 (1)	133
O3—H3···O2^i	0.82	1.77	2.578 (1)	169

Symmetry code: (i) −x+3/2, y−1/2, z.