Literature DB >> 21578901

2-(4-Chloro-phen-oxy)acetohydrazide.

Grzegorz Dutkiewicz, C S Chidan Kumar, B Narayana, H S Yathirajan, Maciej Kubicki.

Abstract

In the title compound, C(8)H(9)ClN(2)O(2), the two planar fragments, i.e. the chloro-phenyl and C-C(=O)-N groups, are inclined at 14.93 (17)°. In the crystal, relatively weak inter-molecular N-H⋯N, C-H⋯O and N-H⋯O hydrogen bonds connect the mol-ecules into layers. The hydro-phobic parts of mol-ecules stick outside these layers and are connected with the neighbouring layers only by van der Waals contacts and Cl⋯Cl inter-actions [3.406 (2) Å].

Entities: Chemical Disease Species

Year: 2009 PMID： 21578901 PMCID： PMC2972103 DOI： 10.1107/S1600536809049538

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

Related literature

For background to hydrazides, see: Cajocorius et al. (1977 ▶); Liu et al. (2006 ▶); Narayana et al. (2005 ▶). For related structures, see: Akhtar et al. (2009 ▶); Lokanath et al. (1998 ▶); Mahendra et al. (2004 ▶); Podyachev et al. (2007 ▶). For graph-set symbols, see: Bernstein et al. (1995 ▶). For halogen–halogen interactions, see: Pedireddi et al. (1994 ▶).

Experimental

Crystal data

C8H9ClN2O2 M = 200.62 Monoclinic, a = 6.444 (1) Å b = 4.011 (1) Å c = 35.369 (4) Å β = 91.89 (1)° V = 913.7 (3) Å3 Z = 4 Mo Kα radiation μ = 0.39 mm−1 T = 295 K 0.4 × 0.4 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire2, large Be window) diffractometer Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.678, T max = 0.944 2864 measured reflections 1761 independent reflections 1448 reflections with I > 2σ(I) R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.058 wR(F 2) = 0.118 S = 1.15 1761 reflections 154 parameters All H-atom parameters refined Δρmax = 0.22 e Å−3 Δρmin = −0.28 e Å−3 Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049538/is2496sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049538/is2496Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₈H₉ClN₂O₂	F(000) = 416
M_r = 200.62	D_x = 1.458 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1266 reflections
a = 6.444 (1) Å	θ = 2.3–26.8°
b = 4.011 (1) Å	µ = 0.39 mm⁻¹
c = 35.369 (4) Å	T = 295 K
β = 91.89 (1)°	Plate, colourless
V = 913.7 (3) Å³	0.4 × 0.4 × 0.15 mm
Z = 4

Oxford Diffraction Xcalibur (Sapphire2, large Be window) diffractometer	1761 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1448 reflections with I > 2σ(I)
graphite	R_int = 0.022
Detector resolution: 8.1929 pixels mm^-1	θ_max = 26.8°, θ_min = 2.3°
ω–scan	h = −8→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −3→4
T_min = 0.678, T_max = 0.944	l = −31→43
2864 measured reflections

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)] = 0.058	Hydrogen site location: difference Fourier map
wR(F²) = 0.118	All H-atom parameters refined
S = 1.15	w = 1/[σ²(F_o²) + (0.0271P)² + 1.1206P] where P = (F_o² + 2F_c²)/3
1761 reflections	(Δ/σ)_max = 0.002
154 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

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
N1	0.7883 (4)	0.5362 (7)	0.75916 (7)	0.0346 (6)
H1A	0.717 (5)	0.733 (11)	0.7541 (10)	0.066 (11)*
H1B	0.711 (5)	0.417 (9)	0.7747 (9)	0.054 (10)*
N2	0.8013 (3)	0.3650 (6)	0.72417 (6)	0.0317 (5)
H2	0.909 (4)	0.247 (8)	0.7201 (8)	0.039 (8)*
C3	0.6568 (4)	0.4000 (7)	0.69716 (7)	0.0300 (6)
O4	0.4957 (3)	0.5630 (6)	0.70086 (5)	0.0425 (5)
C5	0.6937 (4)	0.2401 (8)	0.65965 (8)	0.0341 (6)
H5A	0.573 (5)	0.103 (8)	0.6525 (8)	0.047 (9)*
H5B	0.709 (4)	0.412 (8)	0.6420 (8)	0.043 (8)*
O6	0.8781 (3)	0.0467 (5)	0.66140 (5)	0.0398 (5)
C7	0.9615 (4)	−0.0520 (8)	0.62801 (7)	0.0342 (6)
C8	1.1514 (4)	−0.2151 (8)	0.63137 (8)	0.0412 (7)
H8	1.213 (5)	−0.241 (8)	0.6556 (8)	0.050 (9)*
C9	1.2501 (5)	−0.3162 (9)	0.59971 (9)	0.0478 (8)
H9	1.374 (5)	−0.431 (9)	0.6008 (9)	0.062 (10)*
C10	1.1589 (5)	−0.2639 (9)	0.56450 (8)	0.0473 (8)
C11	0.9690 (5)	−0.1103 (10)	0.56080 (8)	0.0514 (9)
H11	0.902 (5)	−0.092 (9)	0.5362 (9)	0.063 (10)*
C12	0.8682 (5)	−0.0049 (8)	0.59270 (8)	0.0417 (7)
H12	0.742 (5)	0.108 (9)	0.5893 (8)	0.052 (9)*
Cl13	1.28833 (18)	−0.3900 (3)	0.52474 (3)	0.0838 (4)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0321 (12)	0.0390 (16)	0.0327 (12)	−0.0020 (11)	0.0021 (10)	−0.0013 (11)
N2	0.0264 (11)	0.0380 (15)	0.0307 (11)	0.0052 (11)	−0.0004 (9)	−0.0004 (10)
C3	0.0266 (12)	0.0283 (15)	0.0352 (13)	−0.0003 (12)	0.0016 (10)	0.0043 (12)
O4	0.0316 (10)	0.0512 (14)	0.0445 (11)	0.0149 (10)	−0.0025 (8)	0.0003 (10)
C5	0.0307 (14)	0.0371 (17)	0.0342 (14)	0.0034 (13)	−0.0026 (11)	0.0025 (13)
O6	0.0404 (10)	0.0479 (13)	0.0307 (9)	0.0165 (10)	−0.0024 (8)	−0.0001 (9)
C7	0.0363 (14)	0.0361 (17)	0.0301 (13)	−0.0001 (13)	0.0013 (11)	−0.0013 (12)
C8	0.0369 (15)	0.049 (2)	0.0379 (15)	0.0075 (14)	−0.0049 (12)	−0.0007 (14)
C9	0.0384 (16)	0.051 (2)	0.0537 (18)	0.0085 (16)	0.0029 (14)	−0.0046 (16)
C10	0.0562 (19)	0.046 (2)	0.0406 (16)	0.0091 (16)	0.0109 (14)	−0.0036 (14)
C11	0.063 (2)	0.061 (2)	0.0305 (14)	0.0130 (19)	−0.0030 (14)	0.0010 (16)
C12	0.0418 (16)	0.045 (2)	0.0375 (15)	0.0105 (14)	−0.0040 (12)	0.0009 (13)
Cl13	0.0958 (8)	0.1032 (9)	0.0543 (5)	0.0323 (7)	0.0293 (5)	−0.0067 (6)

N1—N2	1.420 (3)	C7—C12	1.381 (4)
N1—H1A	0.93 (4)	C7—C8	1.389 (4)
N1—H1B	0.89 (4)	C8—C9	1.367 (4)
N2—C3	1.319 (3)	C8—H8	0.94 (3)
N2—H2	0.86 (3)	C9—C10	1.376 (4)
C3—O4	1.237 (3)	C9—H9	0.92 (4)
C3—C5	1.499 (4)	C10—C11	1.372 (4)
C5—O6	1.419 (3)	C10—Cl13	1.734 (3)
C5—H5A	0.98 (3)	C11—C12	1.387 (4)
C5—H5B	0.94 (3)	C11—H11	0.96 (3)
O6—C7	1.372 (3)	C12—H12	0.93 (3)

N2—N1—H1A	107 (2)	O6—C7—C8	115.6 (2)
N2—N1—H1B	109 (2)	C12—C7—C8	119.8 (3)
H1A—N1—H1B	107 (3)	C9—C8—C7	120.1 (3)
C3—N2—N1	121.3 (2)	C9—C8—H8	121.4 (19)
C3—N2—H2	119.6 (19)	C7—C8—H8	118.4 (19)
N1—N2—H2	119.0 (19)	C8—C9—C10	120.0 (3)
O4—C3—N2	123.6 (2)	C8—C9—H9	123 (2)
O4—C3—C5	118.5 (2)	C10—C9—H9	117 (2)
N2—C3—C5	117.8 (2)	C11—C10—C9	120.5 (3)
O6—C5—C3	110.6 (2)	C11—C10—Cl13	120.3 (2)
O6—C5—H5A	111.3 (19)	C9—C10—Cl13	119.1 (3)
C3—C5—H5A	108.6 (17)	C10—C11—C12	120.0 (3)
O6—C5—H5B	108.7 (18)	C10—C11—H11	120 (2)
C3—C5—H5B	107.4 (19)	C12—C11—H11	120 (2)
H5A—C5—H5B	110 (3)	C7—C12—C11	119.5 (3)
C7—O6—C5	118.1 (2)	C7—C12—H12	122.2 (19)
O6—C7—C12	124.6 (3)	C11—C12—H12	118.1 (19)

N1—N2—C3—O4	−4.8 (4)	C7—C8—C9—C10	−1.6 (5)
N1—N2—C3—C5	173.5 (2)	C8—C9—C10—C11	0.1 (6)
O4—C3—C5—O6	−176.2 (3)	C8—C9—C10—Cl13	179.3 (3)
N2—C3—C5—O6	5.4 (4)	C9—C10—C11—C12	0.4 (6)
C3—C5—O6—C7	−164.9 (2)	Cl13—C10—C11—C12	−178.9 (3)
C5—O6—C7—C12	−6.7 (4)	O6—C7—C12—C11	178.9 (3)
C5—O6—C7—C8	174.5 (3)	C8—C7—C12—C11	−2.4 (5)
O6—C7—C8—C9	−178.4 (3)	C10—C11—C12—C7	0.8 (6)
C12—C7—C8—C9	2.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.93 (4)	2.51 (4)	3.160 (3)	127 (3)
N1—H1B···O4ⁱⁱ	0.89 (4)	2.15 (4)	3.020 (3)	165 (3)
N2—H2···N1ⁱⁱⁱ	0.86 (3)	2.23 (3)	2.997 (3)	149 (3)
C8—H8···O4^iv	0.94 (3)	2.51 (3)	3.376 (3)	153 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4ⁱ	0.93 (4)	2.51 (4)	3.160 (3)	127 (3)
N1—H1B⋯O4ⁱⁱ	0.89 (4)	2.15 (4)	3.020 (3)	165 (3)
N2—H2⋯N1ⁱⁱⁱ	0.86 (3)	2.23 (3)	2.997 (3)	149 (3)
C8—H8⋯O4^iv	0.94 (3)	2.51 (3)	3.376 (3)	153 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

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