Literature DB >> 21201820

(E)-4-Chloro-N'-(4-hydroxy-benzyl-idene)-benzohydrazide.

Abstract

The mol-ecule of the title compound, C(14)H(11)ClN(2)O(2), displays a trans configuration with respect to the C=N double bond. The dihedral angle between the two benzene rings is 12.8 (3)°. In the crystal structure, mol-ecules are linked through inter-molecular O-H⋯O and N-H⋯O hydrogen bonds and C-H⋯π inter-actions, forming a three-dimensional network.

Entities: Chemical Disease Gene

Year: 2008 PMID： 21201820 PMCID： PMC2960690 DOI： 10.1107/S1600536808027013

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For related structures, see: Yang (2007 ▶, 2008a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶). For related literature, see: Bernardo et al. (1996 ▶); Musie et al. (2001 ▶); Paul et al. (2002 ▶).

Experimental

Crystal data

C14H11ClN2O2 M = 274.70 Orthorhombic, a = 26.251 (3) Å b = 12.376 (3) Å c = 7.786 (2) Å V = 2529.5 (9) Å3 Z = 8 Mo Kα radiation μ = 0.30 mm−1 T = 298 (2) K 0.13 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.963, T max = 0.971 11323 measured reflections 2164 independent reflections 1462 reflections with I > 2σ(I) R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.047 wR(F 2) = 0.116 S = 1.02 2164 reflections 176 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.27 e Å−3 Δρmin = −0.35 e Å−3 Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027013/ci2657sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027013/ci2657Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₁ClN₂O₂	F₀₀₀ = 1136
M_r = 274.70	D_x = 1.443 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1916 reflections
a = 26.251 (3) Å	θ = 2.3–24.5º
b = 12.376 (3) Å	µ = 0.30 mm⁻¹
c = 7.786 (2) Å	T = 298 (2) K
V = 2529.5 (9) Å³	Block, colourless
Z = 8	0.13 × 0.12 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	2164 independent reflections
Radiation source: fine-focus sealed tube	1462 reflections with I > 2σ(I)
Monochromator: graphite	R_int = 0.078
T = 298(2) K	θ_max = 24.9º
ω scans	θ_min = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −30→31
T_min = 0.963, T_max = 0.971	k = −14→11
11323 measured reflections	l = −8→9

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0433P)² + 1.3235P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
2164 reflections	Δρ_max = 0.27 e Å⁻³
176 parameters	Δρ_min = −0.35 e Å⁻³
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	U_iso*/U_eq
Cl1	−0.11993 (3)	0.56136 (8)	−0.02967 (12)	0.0721 (3)
N1	0.15097 (8)	0.76262 (18)	0.3530 (3)	0.0421 (6)
N2	0.10461 (9)	0.74598 (18)	0.2709 (3)	0.0401 (6)
O1	0.37436 (7)	0.92023 (16)	0.5358 (3)	0.0554 (6)
H1	0.3853	0.9786	0.5022	0.083*
O2	0.08473 (7)	0.61751 (14)	0.4644 (2)	0.0412 (5)
C1	0.22762 (10)	0.8643 (2)	0.3633 (3)	0.0378 (7)
C2	0.25323 (10)	0.7913 (2)	0.4685 (4)	0.0450 (7)
H2	0.2372	0.7273	0.5004	0.054*
C3	0.30150 (10)	0.8119 (2)	0.5258 (4)	0.0463 (8)
H3	0.3178	0.7630	0.5979	0.056*
C4	0.32601 (10)	0.9058 (2)	0.4761 (3)	0.0394 (7)
C5	0.30142 (10)	0.9795 (2)	0.3730 (4)	0.0427 (7)
H5	0.3176	1.0435	0.3418	0.051*
C6	0.25282 (10)	0.9580 (2)	0.3163 (4)	0.0440 (7)
H6	0.2366	1.0075	0.2449	0.053*
C7	0.17709 (10)	0.8413 (2)	0.2970 (4)	0.0430 (7)
H7	0.1636	0.8853	0.2116	0.052*
C8	0.07391 (10)	0.6686 (2)	0.3321 (3)	0.0351 (6)
C9	0.02586 (9)	0.6472 (2)	0.2385 (3)	0.0335 (6)
C10	−0.00001 (10)	0.7240 (2)	0.1430 (4)	0.0409 (7)
H10	0.0134	0.7933	0.1331	0.049*
C11	−0.04545 (10)	0.6992 (2)	0.0619 (4)	0.0441 (7)
H11	−0.0628	0.7512	−0.0013	0.053*
C12	−0.06436 (10)	0.5965 (2)	0.0767 (3)	0.0435 (7)
C13	−0.03996 (10)	0.5193 (2)	0.1731 (4)	0.0476 (8)
H13	−0.0536	0.4502	0.1827	0.057*
C14	0.00479 (10)	0.5449 (2)	0.2554 (3)	0.0425 (7)
H14	0.0210	0.4934	0.3229	0.051*
H2A	0.1010 (12)	0.783 (2)	0.172 (2)	0.080*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0490 (5)	0.0779 (6)	0.0895 (7)	−0.0117 (4)	−0.0259 (5)	0.0004 (5)
N1	0.0359 (13)	0.0460 (15)	0.0443 (14)	−0.0041 (11)	−0.0089 (11)	0.0015 (12)
N2	0.0355 (13)	0.0423 (14)	0.0424 (13)	−0.0048 (11)	−0.0094 (11)	0.0047 (11)
O1	0.0404 (13)	0.0531 (14)	0.0726 (15)	−0.0084 (9)	−0.0133 (11)	0.0061 (12)
O2	0.0436 (11)	0.0403 (11)	0.0398 (10)	0.0025 (9)	−0.0063 (9)	0.0053 (9)
C1	0.0356 (16)	0.0400 (16)	0.0379 (15)	−0.0022 (13)	−0.0013 (13)	−0.0006 (13)
C2	0.0419 (17)	0.0391 (16)	0.0539 (18)	−0.0091 (13)	−0.0022 (15)	0.0060 (14)
C3	0.0428 (18)	0.0409 (17)	0.0552 (19)	−0.0001 (13)	−0.0092 (15)	0.0096 (15)
C4	0.0321 (16)	0.0425 (17)	0.0437 (16)	−0.0009 (12)	−0.0019 (13)	−0.0058 (14)
C5	0.0437 (17)	0.0371 (16)	0.0472 (17)	−0.0063 (13)	0.0020 (14)	0.0023 (14)
C6	0.0423 (17)	0.0450 (18)	0.0447 (17)	−0.0012 (14)	−0.0075 (14)	0.0094 (13)
C7	0.0400 (17)	0.0448 (18)	0.0442 (17)	−0.0007 (14)	−0.0071 (13)	0.0045 (14)
C8	0.0365 (16)	0.0323 (15)	0.0365 (15)	0.0047 (13)	−0.0008 (12)	−0.0052 (13)
C9	0.0318 (15)	0.0361 (16)	0.0325 (14)	0.0037 (12)	0.0025 (12)	0.0007 (12)
C10	0.0392 (16)	0.0353 (16)	0.0480 (16)	−0.0046 (13)	−0.0025 (14)	0.0027 (13)
C11	0.0391 (16)	0.0483 (18)	0.0449 (17)	0.0014 (14)	−0.0064 (14)	0.0077 (14)
C12	0.0333 (16)	0.0520 (19)	0.0451 (17)	−0.0032 (14)	−0.0032 (13)	−0.0031 (15)
C13	0.0441 (18)	0.0426 (18)	0.0560 (19)	−0.0116 (14)	−0.0027 (15)	0.0030 (15)
C14	0.0431 (17)	0.0408 (17)	0.0438 (16)	−0.0003 (14)	−0.0046 (14)	0.0064 (14)

Cl1—C12	1.733 (3)	C5—C6	1.376 (4)
N1—C7	1.268 (3)	C5—H5	0.93
N1—N2	1.390 (3)	C6—H6	0.93
N2—C8	1.339 (3)	C7—H7	0.93
N2—H2A	0.899 (10)	C8—C9	1.481 (3)
O1—C4	1.363 (3)	C9—C10	1.385 (3)
O1—H1	0.82	C9—C14	1.387 (4)
O2—C8	1.242 (3)	C10—C11	1.384 (4)
C1—C6	1.385 (4)	C10—H10	0.93
C1—C2	1.392 (4)	C11—C12	1.369 (4)
C1—C7	1.451 (4)	C11—H11	0.93
C2—C3	1.367 (4)	C12—C13	1.373 (4)
C2—H2	0.93	C13—C14	1.375 (4)
C3—C4	1.383 (4)	C13—H13	0.93
C3—H3	0.93	C14—H14	0.93
C4—C5	1.377 (4)

C7—N1—N2	115.4 (2)	N1—C7—H7	119.3
C8—N2—N1	118.0 (2)	C1—C7—H7	119.3
C8—N2—H2A	127 (2)	O2—C8—N2	121.5 (2)
N1—N2—H2A	114 (2)	O2—C8—C9	120.8 (2)
C4—O1—H1	109.5	N2—C8—C9	117.8 (2)
C6—C1—C2	117.9 (2)	C10—C9—C14	118.8 (2)
C6—C1—C7	120.4 (2)	C10—C9—C8	124.0 (2)
C2—C1—C7	121.6 (2)	C14—C9—C8	117.2 (2)
C3—C2—C1	121.2 (3)	C11—C10—C9	121.0 (2)
C3—C2—H2	119.4	C11—C10—H10	119.5
C1—C2—H2	119.4	C9—C10—H10	119.5
C2—C3—C4	119.8 (3)	C12—C11—C10	118.7 (3)
C2—C3—H3	120.1	C12—C11—H11	120.6
C4—C3—H3	120.1	C10—C11—H11	120.6
O1—C4—C5	123.3 (2)	C11—C12—C13	121.5 (3)
O1—C4—C3	116.6 (2)	C11—C12—Cl1	119.8 (2)
C5—C4—C3	120.1 (3)	C13—C12—Cl1	118.7 (2)
C6—C5—C4	119.6 (3)	C12—C13—C14	119.5 (3)
C6—C5—H5	120.2	C12—C13—H13	120.2
C4—C5—H5	120.2	C14—C13—H13	120.2
C5—C6—C1	121.3 (3)	C13—C14—C9	120.4 (3)
C5—C6—H6	119.3	C13—C14—H14	119.8
C1—C6—H6	119.3	C9—C14—H14	119.8
N1—C7—C1	121.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.90 (1)	2.078 (11)	2.970 (3)	171 (3)
O1—H1···O2ⁱⁱ	0.82	1.91	2.725 (3)	170
C6—H6···Cg1ⁱⁱⁱ	0.93	2.88	3.726 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.90 (1)	2.078 (11)	2.970 (3)	171 (3)
O1—H1⋯O2ⁱⁱ	0.82	1.91	2.725 (3)	170
C6—H6⋯Cg1ⁱⁱⁱ	0.93	2.88	3.726 (3)	152

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the C1–C6 ring centroid.

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1. 3-Hydr-oxy-N'-(5-hydr-oxy-2-nitro-benzyl-idene)-2-naphthohydrazide.

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