Literature DB >> 22798795

(E)-4-Amino-N'-(5-chloro-2-hy-droxy-benzyl-idene)benzohydrazide.

Hadi Kargar, Reza Kia, Muhammad Nawaz Tahir.

Abstract

In the title hydrazide Schiff base compound, C(14)H(12)ClN(3)O(2), the conformation around the C=N double bond is E. The dihedral angle between the benzene rings is 41.57 (14) Å. An intra-molecular O-H⋯N hydrogen bond makes an S(6) ring motif. In the crystal, mol-ecules are linked by N-H⋯O (bifurcated acceptor) and N-H⋯N hydrogen bonds, forming chains along the a axis. The inter-esting feature of the crystal structure is the short inter-molecular C⋯O [3.216 (3), 3.170 (3), and 2.992 (3) Å] contacts, one of which is significantly shorter than the sum of the van der Waals radii of these atoms [3.22 Å].

Entities: Chemical Disease Gene Species

Year: 2012 PMID： 22798795 PMCID： PMC3393930 DOI： 10.1107/S1600536812025974

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

Related literature

For the coordination chemistry of Schiff base and hydrazone derivatives, see: Kucukguzel et al. (2006 ▶); Karthikeyan et al. (2006 ▶). For 4-aminobenzohydrazide-derived Schiff base structures, see: Xu (2012 ▶); Shi & Li (2012 ▶); Bakir & Green (2002 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For van der Waals radii, see: Bondi (1964 ▶).

Experimental

Crystal data

C14H12ClN3O2 M = 289.72 Orthorhombic, a = 9.4243 (8) Å b = 9.7975 (9) Å c = 14.1924 (10) Å V = 1310.45 (19) Å3 Z = 4 Mo Kα radiation μ = 0.30 mm−1 T = 296 K 0.30 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.916, T max = 0.938 5390 measured reflections 2157 independent reflections 1871 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.084 S = 1.04 2157 reflections 182 parameters 1 restraint H-atom parameters constrained Δρmax = 0.25 e Å−3 Δρmin = −0.28 e Å−3 Absolute structure: Flack (1983 ▶), 1661 Friedel pairs Flack parameter: −0.02 (8) Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812025974/su2449sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025974/su2449Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812025974/su2449Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₂ClN₃O₂	F(000) = 600
M_r = 289.72	D_x = 1.468 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1125 reflections
a = 9.4243 (8) Å	θ = 2.5–27.4°
b = 9.7975 (9) Å	µ = 0.30 mm⁻¹
c = 14.1924 (10) Å	T = 296 K
V = 1310.45 (19) Å³	Prism, light-yellow
Z = 4	0.30 × 0.25 × 0.22 mm

Bruker SMART APEXII CCD area-detector diffractometer	2157 independent reflections
Radiation source: fine-focus sealed tube	1871 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
φ and ω scans	θ_max = 27.2°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→12
T_min = 0.916, T_max = 0.938	k = −12→9
5390 measured reflections	l = −14→17

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.0457P)² + 0.1075P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2157 reflections	Δρ_max = 0.25 e Å⁻³
182 parameters	Δρ_min = −0.28 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1661 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (8)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.25011 (8)	0.53141 (8)	−0.12609 (6)	0.0608 (2)
O1	−0.18920 (19)	0.6731 (2)	0.14787 (13)	0.0576 (6)
H1	−0.1557	0.6890	0.2001	0.086*
O2	−0.14326 (17)	0.8456 (2)	0.38803 (12)	0.0433 (5)
N1	0.0101 (2)	0.6912 (2)	0.27231 (13)	0.0357 (5)
N2	0.0530 (2)	0.7181 (2)	0.36316 (14)	0.0348 (5)
H2	0.1501	0.6912	0.3791	0.042*
N3	0.1425 (3)	0.8793 (3)	0.79456 (16)	0.0608 (7)
H3A	0.1989	0.8266	0.8306	0.073*
H3B	0.1185	0.9611	0.8284	0.073*
C1	0.0540 (3)	0.6151 (3)	0.11808 (16)	0.0343 (6)
C2	−0.0834 (3)	0.6413 (3)	0.08747 (18)	0.0401 (6)
C3	−0.1161 (3)	0.6341 (3)	−0.00784 (18)	0.0452 (7)
H3	−0.2084	0.6516	−0.0277	0.054*
C4	−0.0146 (3)	0.6016 (3)	−0.07299 (17)	0.0436 (7)
H4	−0.0368	0.5995	−0.1368	0.052*
C5	0.1210 (3)	0.5721 (3)	−0.04292 (18)	0.0409 (6)
C6	0.1556 (3)	0.5765 (3)	0.05102 (18)	0.0413 (6)
H6	0.2469	0.5538	0.0703	0.050*
C7	0.0965 (3)	0.6349 (3)	0.21540 (17)	0.0371 (6)
H7	0.1856	0.6069	0.2359	0.045*
C8	−0.0326 (3)	0.7949 (3)	0.41874 (17)	0.0337 (6)
C9	0.0153 (2)	0.8152 (3)	0.51641 (17)	0.0327 (6)
C10	0.1079 (3)	0.7271 (3)	0.56124 (18)	0.0451 (7)
H10	0.1439	0.6526	0.5284	0.054*
C11	0.1479 (3)	0.7471 (3)	0.65323 (18)	0.0492 (7)
H11	0.2087	0.6851	0.6820	0.059*
C12	0.0986 (3)	0.8585 (3)	0.70364 (17)	0.0397 (6)
C13	0.0065 (3)	0.9481 (3)	0.65961 (18)	0.0422 (6)
H13	−0.0274	1.0237	0.6922	0.051*
C14	−0.0354 (3)	0.9260 (3)	0.56763 (19)	0.0408 (6)
H14	−0.0987	0.9863	0.5394	0.049*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0686 (4)	0.0770 (5)	0.0367 (3)	0.0182 (4)	0.0054 (4)	−0.0052 (4)
O1	0.0410 (10)	0.0937 (18)	0.0380 (11)	0.0132 (11)	−0.0035 (9)	−0.0045 (12)
O2	0.0346 (9)	0.0579 (12)	0.0375 (11)	0.0050 (8)	−0.0085 (8)	0.0032 (10)
N1	0.0394 (11)	0.0443 (13)	0.0233 (10)	−0.0043 (9)	−0.0059 (9)	0.0007 (9)
N2	0.0343 (10)	0.0477 (13)	0.0223 (10)	0.0009 (10)	−0.0055 (9)	0.0001 (10)
N3	0.0859 (18)	0.0627 (19)	0.0338 (13)	0.0048 (14)	−0.0158 (12)	−0.0128 (13)
C1	0.0382 (14)	0.0355 (14)	0.0291 (13)	−0.0005 (11)	−0.0069 (11)	0.0009 (12)
C2	0.0394 (14)	0.0466 (18)	0.0342 (13)	−0.0009 (13)	−0.0055 (12)	0.0016 (13)
C3	0.0443 (16)	0.0535 (18)	0.0377 (15)	0.0016 (13)	−0.0122 (13)	−0.0011 (13)
C4	0.0592 (18)	0.0452 (16)	0.0265 (13)	0.0014 (13)	−0.0117 (12)	−0.0025 (13)
C5	0.0526 (16)	0.0383 (16)	0.0317 (13)	0.0027 (12)	−0.0010 (12)	−0.0010 (13)
C6	0.0414 (15)	0.0480 (16)	0.0345 (14)	0.0057 (13)	−0.0091 (11)	−0.0008 (13)
C7	0.0324 (13)	0.0469 (17)	0.0320 (13)	0.0001 (12)	−0.0075 (11)	0.0028 (13)
C8	0.0327 (13)	0.0370 (14)	0.0313 (13)	−0.0053 (11)	−0.0050 (11)	0.0045 (12)
C9	0.0303 (13)	0.0398 (14)	0.0279 (12)	−0.0013 (11)	−0.0008 (10)	0.0000 (11)
C10	0.0593 (17)	0.0438 (17)	0.0323 (15)	0.0127 (14)	−0.0052 (13)	−0.0053 (13)
C11	0.0669 (18)	0.0450 (16)	0.0357 (14)	0.0155 (14)	−0.0133 (14)	0.0005 (13)
C12	0.0451 (15)	0.0457 (17)	0.0283 (12)	−0.0045 (13)	0.0010 (12)	−0.0025 (13)
C13	0.0424 (14)	0.0446 (15)	0.0395 (15)	0.0015 (13)	0.0030 (12)	−0.0095 (14)
C14	0.0367 (13)	0.0452 (16)	0.0406 (15)	0.0060 (13)	−0.0019 (12)	0.0021 (13)

Cl1—C5	1.742 (3)	C4—C5	1.378 (4)
O1—C2	1.351 (3)	C4—H4	0.9300
O1—H1	0.8200	C5—C6	1.373 (3)
O2—C8	1.235 (3)	C6—H6	0.9300
N1—C7	1.272 (3)	C7—H7	0.9300
N1—N2	1.377 (3)	C8—C9	1.471 (3)
N2—C8	1.357 (3)	C9—C10	1.382 (4)
N2—H2	0.9783	C9—C14	1.392 (4)
N3—C12	1.370 (3)	C10—C11	1.373 (4)
N3—H3A	0.9001	C10—H10	0.9300
N3—H3B	0.9616	C11—C12	1.385 (4)
C1—C2	1.390 (3)	C11—H11	0.9300
C1—C6	1.402 (3)	C12—C13	1.383 (4)
C1—C7	1.451 (3)	C13—C14	1.381 (4)
C2—C3	1.389 (4)	C13—H13	0.9300
C3—C4	1.368 (4)	C14—H14	0.9300
C3—H3	0.9300

C2—O1—H1	109.5	C1—C6—H6	119.8
C7—N1—N2	119.3 (2)	N1—C7—C1	119.1 (2)
C8—N2—N1	118.43 (19)	N1—C7—H7	120.5
C8—N2—H2	124.8	C1—C7—H7	120.5
N1—N2—H2	116.1	O2—C8—N2	121.4 (2)
C12—N3—H3A	128.9	O2—C8—C9	122.5 (2)
C12—N3—H3B	121.5	N2—C8—C9	116.1 (2)
H3A—N3—H3B	109.5	C10—C9—C14	117.6 (2)
C2—C1—C6	118.3 (2)	C10—C9—C8	122.9 (2)
C2—C1—C7	122.0 (2)	C14—C9—C8	119.5 (2)
C6—C1—C7	119.6 (2)	C11—C10—C9	121.5 (3)
O1—C2—C3	117.8 (2)	C11—C10—H10	119.3
O1—C2—C1	122.1 (2)	C9—C10—H10	119.3
C3—C2—C1	120.1 (2)	C10—C11—C12	120.8 (3)
C4—C3—C2	121.0 (2)	C10—C11—H11	119.6
C4—C3—H3	119.5	C12—C11—H11	119.6
C2—C3—H3	119.5	N3—C12—C13	121.4 (3)
C3—C4—C5	119.2 (2)	N3—C12—C11	120.2 (3)
C3—C4—H4	120.4	C13—C12—C11	118.5 (2)
C5—C4—H4	120.4	C14—C13—C12	120.5 (3)
C6—C5—C4	121.0 (2)	C14—C13—H13	119.8
C6—C5—Cl1	119.9 (2)	C12—C13—H13	119.8
C4—C5—Cl1	119.1 (2)	C13—C14—C9	121.2 (2)
C5—C6—C1	120.4 (2)	C13—C14—H14	119.4
C5—C6—H6	119.8	C9—C14—H14	119.4

C7—N1—N2—C8	170.8 (2)	N1—N2—C8—O2	−3.4 (3)
C6—C1—C2—O1	177.0 (3)	N1—N2—C8—C9	177.3 (2)
C7—C1—C2—O1	−7.1 (4)	O2—C8—C9—C10	157.6 (3)
C6—C1—C2—C3	−2.4 (4)	N2—C8—C9—C10	−23.1 (3)
C7—C1—C2—C3	173.6 (3)	O2—C8—C9—C14	−21.3 (4)
O1—C2—C3—C4	−179.6 (3)	N2—C8—C9—C14	158.0 (2)
C1—C2—C3—C4	−0.2 (5)	C14—C9—C10—C11	0.5 (4)
C2—C3—C4—C5	1.8 (4)	C8—C9—C10—C11	−178.4 (3)
C3—C4—C5—C6	−0.8 (4)	C9—C10—C11—C12	−1.4 (5)
C3—C4—C5—Cl1	−179.8 (2)	C10—C11—C12—N3	−178.2 (3)
C4—C5—C6—C1	−1.8 (4)	C10—C11—C12—C13	1.0 (4)
Cl1—C5—C6—C1	177.2 (2)	N3—C12—C13—C14	179.4 (3)
C2—C1—C6—C5	3.4 (4)	C11—C12—C13—C14	0.3 (4)
C7—C1—C6—C5	−172.7 (3)	C12—C13—C14—C9	−1.1 (4)
N2—N1—C7—C1	−175.9 (2)	C10—C9—C14—C13	0.7 (4)
C2—C1—C7—N1	−7.4 (4)	C8—C9—C14—C13	179.7 (2)
C6—C1—C7—N1	168.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.584 (3)	145
N2—H2···O2ⁱ	0.98	1.98	2.951 (3)	169
N3—H3B···O2ⁱⁱ	0.96	2.09	3.004 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.87	2.584 (3)	145
N2—H2⋯O2ⁱ	0.98	1.98	2.951 (3)	169
N3—H3B⋯O2ⁱⁱ	0.96	2.09	3.004 (3)	159

Symmetry codes: (i) ; (ii) .

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