Literature DB >> 22590408

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

Abstract

The title compound, C(14)H(12)ClN(3)O(2), displays an E conformation with respect to the C=N double bond. The dihedral angle between the benzene rings is 41.3 (5)°. The mol-ecular structure is stabilized by an intra-molecular O-H⋯N hydrogen bond. In the crystal, N-H⋯O and weak N-H⋯Cl hydrogen bonds link the mol-ecules into a three-dimensional architecture. In addition, there are weak C-H⋯π stacking inter-actions.

Entities: Chemical Disease Species

Year: 2012 PMID： 22590408 PMCID： PMC3344646 DOI： 10.1107/S160053681201803X

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

Related literature

For the biological properties of Schiff base and hydrazone compounds, see: Kucukguzel et al. (2006 ▶); Khattab (2005 ▶); Karthikeyan et al. (2006 ▶). For closely related structures and background references, see: Bernhardt et al. (2003 ▶, 2005 ▶); Armstrong et al. (2003 ▶); Cao (2009 ▶); Yang (2009 ▶); Zhou & Yang (2010 ▶); Zhang et al., (2009 ▶).

Experimental

Crystal data

C14H12ClN3O2 M = 289.72 Orthorhombic, a = 9.3375 (16) Å b = 9.7194 (16) Å c = 14.214 (3) Å V = 1290.0 (4) Å3 Z = 4 Mo Kα radiation μ = 0.30 mm−1 T = 296 K 0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.947, T max = 0.970 8516 measured reflections 2944 independent reflections 2866 reflections with I > 2σ(I) R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.084 S = 1.10 2944 reflections 182 parameters H-atom parameters constrained Δρmax = 0.36 e Å−3 Δρmin = −0.16 e Å−3 Absolute structure: Flack (1983 ▶), 1407 Friedel pairs Flack parameter: 0.09 (9) Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201803X/tk5088sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201803X/tk5088Isup2.hkl Supplementary material file. DOI: 10.1107/S160053681201803X/tk5088Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₂ClN₃O₂	F(000) = 600
M_r = 289.72	D_x = 1.487 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 6341 reflections
a = 9.3375 (16) Å	θ = 1.4–27.5°
b = 9.7194 (16) Å	µ = 0.30 mm⁻¹
c = 14.214 (3) Å	T = 296 K
V = 1290.0 (4) Å³	Block, yellow
Z = 4	0.20 × 0.15 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	2944 independent reflections
Radiation source: fine-focus sealed tube	2866 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
φ and ω scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
T_min = 0.947, T_max = 0.970	k = −12→9
8516 measured reflections	l = −18→18

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)] = 0.033	H-atom parameters constrained
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.0553P)² + 0.2086P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
2944 reflections	Δρ_max = 0.36 e Å⁻³
182 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1407 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.09 (9)

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	0.75084 (6)	0.97018 (6)	0.79216 (7)	0.03468 (17)
O1	1.14409 (16)	0.65129 (17)	0.27805 (12)	0.0267 (4)
O2	1.19222 (18)	0.8254 (2)	0.51735 (12)	0.0343 (4)
H2	1.1593	0.8184	0.4641	0.051*
N1	0.8561 (3)	0.6238 (2)	−0.12949 (16)	0.0377 (5)
H1A	0.7980	0.6813	−0.1551	0.045*
H1B	0.8867	0.5542	−0.1610	0.045*
N2	0.94718 (19)	0.78349 (19)	0.30263 (14)	0.0224 (4)
H2A	0.8682	0.8164	0.2816	0.027*
N3	0.9907 (2)	0.8088 (2)	0.39290 (13)	0.0224 (4)
C1	0.8999 (2)	0.6432 (2)	−0.03874 (17)	0.0262 (5)
C2	0.9933 (3)	0.5508 (2)	0.00555 (18)	0.0270 (5)
H2B	1.0272	0.4748	−0.0273	0.032*
C3	1.0352 (2)	0.5718 (2)	0.09760 (17)	0.0255 (5)
H3	1.0982	0.5103	0.1257	0.031*
C4	0.9840 (2)	0.6846 (2)	0.14908 (16)	0.0220 (4)
C5	0.8906 (3)	0.7754 (3)	0.10492 (17)	0.0286 (5)
H5	0.8548	0.8503	0.1382	0.034*
C6	0.8504 (3)	0.7562 (3)	0.01244 (17)	0.0308 (5)
H6	0.7895	0.8193	−0.0161	0.037*
C7	1.0335 (2)	0.7040 (2)	0.24690 (16)	0.0220 (4)
C8	0.9037 (2)	0.8682 (2)	0.45000 (17)	0.0239 (5)
H8	0.8149	0.8985	0.4294	0.029*
C9	0.9471 (2)	0.8871 (2)	0.54757 (16)	0.0230 (4)
C10	1.0863 (2)	0.8585 (2)	0.57817 (17)	0.0247 (5)
C11	1.1199 (2)	0.8632 (2)	0.67355 (18)	0.0274 (5)
H11	1.2124	0.8434	0.6930	0.033*
C12	1.0177 (3)	0.8968 (2)	0.73943 (16)	0.0268 (5)
H12	1.0402	0.8979	0.8031	0.032*
C13	0.8807 (3)	0.9291 (2)	0.70915 (17)	0.0256 (5)
C14	0.8452 (3)	0.9260 (2)	0.61485 (16)	0.0253 (5)
H14	0.7534	0.9497	0.5959	0.030*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0388 (3)	0.0439 (3)	0.0213 (3)	0.0096 (2)	0.0028 (2)	−0.0028 (3)
O1	0.0207 (7)	0.0360 (8)	0.0235 (9)	0.0020 (6)	−0.0044 (6)	0.0024 (7)
O2	0.0268 (9)	0.0562 (11)	0.0198 (8)	0.0067 (8)	−0.0026 (7)	0.0004 (8)
N1	0.0550 (14)	0.0359 (11)	0.0221 (11)	0.0034 (10)	−0.0080 (10)	−0.0054 (9)
N2	0.0218 (8)	0.0301 (9)	0.0155 (8)	0.0004 (7)	−0.0036 (7)	0.0002 (7)
N3	0.0232 (9)	0.0287 (9)	0.0152 (8)	−0.0022 (7)	−0.0037 (7)	0.0020 (7)
C1	0.0289 (11)	0.0308 (12)	0.0188 (10)	−0.0055 (9)	−0.0003 (8)	0.0001 (9)
C2	0.0284 (11)	0.0270 (10)	0.0254 (11)	0.0000 (9)	0.0027 (9)	−0.0042 (10)
C3	0.0228 (10)	0.0289 (11)	0.0247 (12)	0.0021 (9)	−0.0020 (9)	−0.0010 (9)
C4	0.0227 (10)	0.0267 (10)	0.0166 (10)	−0.0023 (8)	−0.0013 (8)	−0.0002 (8)
C5	0.0374 (12)	0.0291 (11)	0.0195 (11)	0.0054 (9)	−0.0026 (9)	−0.0010 (9)
C6	0.0403 (14)	0.0317 (11)	0.0206 (11)	0.0065 (10)	−0.0077 (10)	0.0004 (9)
C7	0.0236 (10)	0.0239 (10)	0.0185 (11)	−0.0033 (8)	−0.0003 (9)	0.0029 (8)
C8	0.0235 (10)	0.0288 (11)	0.0195 (11)	−0.0007 (8)	−0.0047 (8)	0.0018 (9)
C9	0.0271 (11)	0.0239 (10)	0.0180 (10)	−0.0009 (8)	−0.0033 (8)	0.0010 (9)
C10	0.0263 (11)	0.0274 (10)	0.0205 (11)	0.0000 (8)	−0.0032 (9)	−0.0010 (9)
C11	0.0258 (11)	0.0325 (11)	0.0239 (12)	0.0019 (9)	−0.0093 (9)	−0.0012 (9)
C12	0.0360 (12)	0.0299 (11)	0.0146 (10)	0.0002 (9)	−0.0062 (9)	−0.0001 (9)
C13	0.0322 (12)	0.0248 (10)	0.0197 (11)	0.0011 (8)	0.0015 (9)	−0.0022 (9)
C14	0.0252 (11)	0.0293 (10)	0.0215 (11)	0.0019 (9)	−0.0033 (8)	0.0009 (9)

Cl1—C13	1.741 (2)	C4—C5	1.392 (3)
O1—C7	1.235 (2)	C4—C7	1.479 (3)
O2—C10	1.355 (3)	C5—C6	1.381 (3)
O2—H2	0.8200	C5—H5	0.9300
N1—C1	1.367 (3)	C6—H6	0.9300
N1—H1A	0.8600	C8—C9	1.458 (3)
N1—H1B	0.8600	C8—H8	0.9300
N2—N3	1.369 (3)	C9—C10	1.399 (3)
N2—C7	1.370 (3)	C9—C14	1.403 (3)
N2—H2A	0.8600	C10—C11	1.393 (3)
N3—C8	1.287 (3)	C11—C12	1.378 (3)
C1—C6	1.396 (3)	C11—H11	0.9300
C1—C2	1.402 (3)	C12—C13	1.390 (3)
C2—C3	1.382 (3)	C12—H12	0.9300
C2—H2B	0.9300	C13—C14	1.382 (3)
C3—C4	1.402 (3)	C14—H14	0.9300
C3—H3	0.9300

C10—O2—H2	109.5	C1—C6—H6	119.6
C1—N1—H1A	120.0	O1—C7—N2	121.3 (2)
C1—N1—H1B	120.0	O1—C7—C4	123.1 (2)
H1A—N1—H1B	120.0	N2—C7—C4	115.54 (19)
N3—N2—C7	117.90 (19)	N3—C8—C9	118.7 (2)
N3—N2—H2A	121.1	N3—C8—H8	120.6
C7—N2—H2A	121.1	C9—C8—H8	120.6
C8—N3—N2	118.93 (19)	C10—C9—C14	118.3 (2)
N1—C1—C6	120.1 (2)	C10—C9—C8	122.0 (2)
N1—C1—C2	121.5 (2)	C14—C9—C8	119.6 (2)
C6—C1—C2	118.4 (2)	O2—C10—C11	117.7 (2)
C3—C2—C1	120.6 (2)	O2—C10—C9	122.0 (2)
C3—C2—H2B	119.7	C11—C10—C9	120.4 (2)
C1—C2—H2B	119.7	C12—C11—C10	120.9 (2)
C2—C3—C4	120.8 (2)	C12—C11—H11	119.6
C2—C3—H3	119.6	C10—C11—H11	119.6
C4—C3—H3	119.6	C11—C12—C13	119.0 (2)
C5—C4—C3	118.3 (2)	C11—C12—H12	120.5
C5—C4—C7	122.7 (2)	C13—C12—H12	120.5
C3—C4—C7	118.9 (2)	C14—C13—C12	121.2 (2)
C6—C5—C4	121.0 (2)	C14—C13—Cl1	119.69 (19)
C6—C5—H5	119.5	C12—C13—Cl1	119.13 (18)
C4—C5—H5	119.5	C13—C14—C9	120.3 (2)
C5—C6—C1	120.8 (2)	C13—C14—H14	119.9
C5—C6—H6	119.6	C9—C14—H14	119.9

C7—N2—N3—C8	−171.4 (2)	N2—N3—C8—C9	176.14 (19)
N1—C1—C2—C3	−179.5 (2)	N3—C8—C9—C10	8.1 (3)
C6—C1—C2—C3	−0.2 (4)	N3—C8—C9—C14	−167.4 (2)
C1—C2—C3—C4	0.9 (4)	C14—C9—C10—O2	−177.5 (2)
C2—C3—C4—C5	−0.5 (3)	C8—C9—C10—O2	6.9 (3)
C2—C3—C4—C7	−179.1 (2)	C14—C9—C10—C11	2.7 (3)
C3—C4—C5—C6	−0.7 (4)	C8—C9—C10—C11	−172.9 (2)
C7—C4—C5—C6	177.9 (2)	O2—C10—C11—C12	179.7 (2)
C4—C5—C6—C1	1.4 (4)	C9—C10—C11—C12	−0.4 (4)
N1—C1—C6—C5	178.3 (2)	C10—C11—C12—C13	−1.4 (4)
C2—C1—C6—C5	−1.0 (4)	C11—C12—C13—C14	1.0 (4)
N3—N2—C7—O1	3.3 (3)	C11—C12—C13—Cl1	179.46 (18)
N3—N2—C7—C4	−177.71 (18)	C12—C13—C14—C9	1.3 (4)
C5—C4—C7—O1	−158.2 (2)	Cl1—C13—C14—C9	−177.17 (17)
C3—C4—C7—O1	20.4 (3)	C10—C9—C14—C13	−3.1 (3)
C5—C4—C7—N2	22.8 (3)	C8—C9—C14—C13	172.6 (2)
C3—C4—C7—N2	−158.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.12	2.921 (2)	156
N1—H1A···Cl1ⁱⁱ	0.86	2.94	3.680 (2)	145
N1—H1B···O1ⁱⁱⁱ	0.86	2.19	2.978 (3)	151
O2—H2···N3	0.82	1.88	2.588 (3)	145
C5—H5···Cg2^iv	0.93	2.92	3.473 (3)	120
C14—H14···Cg1^v	0.93	2.83	3.641 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.86	2.12	2.921 (2)	156
N1—H1A⋯Cl1ⁱⁱ	0.86	2.94	3.680 (2)	145
N1—H1B⋯O1ⁱⁱⁱ	0.86	2.19	2.978 (3)	151
O2—H2⋯N3	0.82	1.88	2.588 (3)	145
C5—H5⋯Cg2^iv	0.93	2.92	3.473 (3)	120
C14—H14⋯Cg1^v	0.93	2.83	3.641 (3)	147

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

10 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Synthesis and biological activity of 4-thiazolidinones, thiosemicarbazides derived from diflunisal hydrazide.

Authors: Güniz Küçükgüzel; Ayla Kocatepe; Erik De Clercq; Fikrettin Sahin; Medine Güllüce
Journal: Eur J Med Chem Date: 2006-01-18 Impact factor: 6.514

3. Synthesis and biological activity of Schiff and Mannich bases bearing 2,4-dichloro-5-fluorophenyl moiety.

Authors: Mari Sithambaram Karthikeyan; Dasappa Jagadeesh Prasad; Boja Poojary; K Subrahmanya Bhat; Bantwal Shivarama Holla; Nalilu Suchetha Kumari
Journal: Bioorg Med Chem Date: 2006-08-01 Impact factor: 3.641

4. Novel diaroylhydrazine ligands as iron chelators: coordination chemistry and biological activity.

Authors: Paul V Bernhardt; Piao Chin; Philip C Sharpe; Jing-Yan C Wang; Des R Richardson
Journal: J Biol Inorg Chem Date: 2005-11-08 Impact factor: 3.358

5. (E)-4-Bromo-N'-(2-nitro-benzyl-idene)benzohydrazide.

Authors: Ming-Jun Zhang; Li-Zi Yin; Da-Cheng Wang; Xu-Ming Deng; Jing-Bo Liu
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-02-11

6. N'-(5-Hydr-oxy-2-nitro-benzyl-idene)-2-methoxy-benzohydrazide.

Authors: De-Suo Yang
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-10-28

7. Cytotoxic iron chelators: characterization of the structure, solution chemistry and redox activity of ligands and iron complexes of the di-2-pyridyl ketone isonicotinoyl hydrazone (HPKIH) analogues.

Authors: Paul V Bernhardt; Lorraine M Caldwell; Timothy B Chaston; Piao Chin; Des R Richardson
Journal: J Biol Inorg Chem Date: 2003-10-15 Impact factor: 3.358

8. (E)-4-Chloro-N'-(5-hydr-oxy-2-nitro-benzyl-idene)benzohydrazide.

Authors: Guo-Biao Cao
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-09-09

9. 2-Chloro-N'-(5-hydr-oxy-2-nitro-benzyl-idene)benzohydrazide.

Authors: Cong-Shan Zhou; Tao Yang
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-01-16

10. Synthesis and biological activity of novel amino acid-(N'-benzoyl) hydrazide and amino acid-(N'-nicotinoyl) hydrazide derivatives.

Authors: Sherine N Khattab
Journal: Molecules Date: 2005-09-30 Impact factor: 4.411