Literature DB >> 21582613

N'-(5-Chloro-2-hydroxy-benzyl-idene)-3,4,5-trihydroxy-benzohydrazide dihydrate.

Abeer A Abdul Alhadi¹, Hapipah Mohd Ali, Seik Weng Ng.

Abstract

The benzohydrazide mol-ecule in the title dihydrate, C(14)H(11)ClN(2)O(5)·2H(2)O, is non-planar, with the two aromatic rings at either side of the -C(=O)-NH-N=CH- unit forming a dihedral angle of 29.7 (2)°. The benzohydrazide mol-ecule is linked to the water mol-ecules by O-H⋯O and N-H⋯O hydrogen bonds, with other O-H⋯O hydrogen bonds leading to a layer structure.

Entities: Chemical Disease Species

Year: 2009 PMID： 21582613 PMCID： PMC2968776 DOI： 10.1107/S1600536809010812

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

Related literature

For the the parent N′-(2-hydroxybenzylidene)benzohydrazide, see: Lyubchova et al. (1995 ▶). For other N′-(2-hydroxy-5-nitrobenzylidene)benzohydrazides, see: Ali et al. (2005 ▶); Lyubchova et al. (1995 ▶); Xu & Liu (2006 ▶).

Experimental

Crystal data

C14H11ClN2O5·2H2O M = 358.73 Monoclinic, a = 30.5627 (12) Å b = 3.7539 (2) Å c = 12.8882 (5) Å β = 90.450 (3)° V = 1478.61 (11) Å3 Z = 4 Mo Kα radiation μ = 0.30 mm−1 T = 100 K 0.36 × 0.04 × 0.04 mm

Data collection

Bruker SMART APEX diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.899, T max = 0.988 10104 measured reflections 2623 independent reflections 1801 reflections with I > 2σ(I) R int = 0.097

Refinement

R[F 2 > 2σ(F 2)] = 0.071 wR(F 2) = 0.181 S = 1.07 2623 reflections 221 parameters H-atom parameters constrained Δρmax = 0.38 e Å−3 Δρmin = −0.49 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010812/tk2403sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010812/tk2403Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₁ClN₂O₅·2H₂O	F(000) = 744
M_r = 358.73	D_x = 1.611 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1505 reflections
a = 30.5627 (12) Å	θ = 2.7–24.3°
b = 3.7539 (2) Å	µ = 0.30 mm⁻¹
c = 12.8882 (5) Å	T = 100 K
β = 90.450 (3)°	Prism, yellow
V = 1478.61 (11) Å³	0.36 × 0.04 × 0.04 mm
Z = 4

Bruker SMART APEX diffractometer	2623 independent reflections
Radiation source: fine-focus sealed tube	1801 reflections with I > 2σ(I)
graphite	R_int = 0.097
ω scans	θ_max = 25.0°, θ_min = 0.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −36→36
T_min = 0.899, T_max = 0.988	k = −4→4
10104 measured reflections	l = −15→14

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.181	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0537P)² + 5.5995P] where P = (F_o² + 2F_c²)/3
2623 reflections	(Δ/σ)_max = 0.001
221 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

	x	y	z	U_iso*/U_eq
Cl1	0.53161 (4)	0.3168 (4)	0.59750 (10)	0.0244 (3)
O1	0.67086 (11)	0.6471 (10)	0.8994 (2)	0.0243 (9)
H1	0.6933	0.7236	0.8694	0.036*
O2	0.79657 (11)	0.9733 (10)	0.8420 (2)	0.0232 (9)
O3	0.94472 (12)	1.3696 (12)	0.7043 (3)	0.0349 (10)
H3	0.9663	1.3279	0.6661	0.052*
O4	0.94729 (12)	1.0933 (13)	0.5106 (3)	0.0395 (12)
H4	0.9481	0.9332	0.4651	0.059*
O5	0.87480 (11)	0.7706 (11)	0.4244 (2)	0.0245 (9)
H5	0.8498	0.7191	0.4013	0.037*
O1w	0.97110 (13)	0.8480 (13)	0.8663 (4)	0.0542 (14)
H11	0.9676	0.9037	0.8040	0.081*
H12	0.9666	1.0253	0.9042	0.081*
O2w	0.73755 (11)	0.1847 (10)	0.9961 (2)	0.0239 (8)
H21	0.7141	0.2633	0.9700	0.036*
H22	0.7554	0.1438	0.9482	0.036*
N1	0.71793 (13)	0.8677 (12)	0.7419 (3)	0.0194 (10)
N2	0.75565 (13)	0.9864 (12)	0.6939 (3)	0.0187 (9)
H2	0.7545	1.0529	0.6284	0.022*
C1	0.63896 (16)	0.5781 (13)	0.8275 (4)	0.0179 (11)
C2	0.60017 (17)	0.4266 (14)	0.8603 (4)	0.0209 (12)
H2A	0.5965	0.3740	0.9318	0.025*
C3	0.56699 (17)	0.3513 (14)	0.7916 (4)	0.0233 (12)
H3A	0.5403	0.2508	0.8151	0.028*
C4	0.57295 (16)	0.4243 (13)	0.6865 (4)	0.0189 (11)
C5	0.61125 (16)	0.5725 (13)	0.6514 (4)	0.0193 (11)
H5A	0.6148	0.6213	0.5797	0.023*
C6	0.64514 (16)	0.6516 (14)	0.7219 (4)	0.0179 (11)
C7	0.68550 (15)	0.7976 (13)	0.6815 (4)	0.0172 (11)
H7	0.6880	0.8421	0.6092	0.021*
C9	0.79416 (16)	1.0018 (14)	0.7457 (4)	0.0181 (11)
C10	0.83308 (16)	1.0434 (14)	0.6800 (4)	0.0183 (11)
C11	0.87050 (16)	1.1993 (15)	0.7207 (4)	0.0214 (12)
H11A	0.8704	1.2939	0.7890	0.026*
C12	0.90791 (16)	1.2173 (16)	0.6620 (4)	0.0266 (13)
C13	0.90870 (16)	1.0734 (15)	0.5623 (4)	0.0241 (13)
C14	0.87108 (16)	0.9157 (15)	0.5212 (4)	0.0219 (12)
C15	0.83293 (16)	0.9046 (14)	0.5784 (4)	0.0189 (11)
H15	0.8070	0.8046	0.5496	0.023*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0204 (7)	0.0272 (7)	0.0257 (7)	−0.0018 (6)	−0.0025 (5)	−0.0039 (6)
O1	0.026 (2)	0.031 (2)	0.0151 (17)	−0.0024 (18)	−0.0023 (15)	−0.0001 (17)
O2	0.0211 (19)	0.036 (2)	0.0122 (18)	0.0034 (17)	−0.0014 (14)	−0.0031 (16)
O3	0.022 (2)	0.049 (3)	0.034 (2)	−0.014 (2)	−0.0055 (17)	0.006 (2)
O4	0.021 (2)	0.070 (4)	0.028 (2)	−0.009 (2)	0.0042 (17)	0.011 (2)
O5	0.0199 (18)	0.042 (2)	0.0118 (17)	−0.0017 (18)	0.0023 (14)	−0.0004 (17)
O1w	0.027 (2)	0.056 (3)	0.079 (3)	0.013 (2)	0.012 (2)	0.017 (3)
O2w	0.0223 (18)	0.035 (2)	0.0139 (17)	0.0042 (17)	−0.0002 (14)	−0.0012 (17)
N1	0.015 (2)	0.024 (2)	0.019 (2)	0.0020 (18)	−0.0001 (17)	0.0006 (19)
N2	0.018 (2)	0.026 (2)	0.0121 (19)	−0.0012 (19)	0.0017 (17)	−0.0016 (19)
C1	0.023 (3)	0.016 (3)	0.014 (2)	0.002 (2)	−0.001 (2)	0.002 (2)
C2	0.027 (3)	0.022 (3)	0.013 (2)	0.002 (2)	0.005 (2)	0.000 (2)
C3	0.022 (3)	0.023 (3)	0.026 (3)	0.000 (2)	0.009 (2)	0.000 (2)
C4	0.017 (3)	0.017 (3)	0.023 (3)	0.001 (2)	0.000 (2)	−0.003 (2)
C5	0.025 (3)	0.020 (3)	0.013 (2)	0.004 (2)	0.001 (2)	0.000 (2)
C6	0.022 (3)	0.018 (3)	0.014 (2)	0.002 (2)	0.002 (2)	−0.001 (2)
C7	0.024 (3)	0.016 (3)	0.011 (2)	0.005 (2)	0.003 (2)	0.001 (2)
C9	0.021 (3)	0.018 (3)	0.015 (3)	0.001 (2)	−0.001 (2)	0.002 (2)
C10	0.019 (3)	0.023 (3)	0.013 (2)	0.003 (2)	−0.003 (2)	0.006 (2)
C11	0.022 (3)	0.024 (3)	0.018 (3)	0.001 (2)	−0.004 (2)	0.001 (2)
C12	0.019 (3)	0.036 (3)	0.025 (3)	−0.007 (2)	−0.006 (2)	0.013 (3)
C13	0.017 (3)	0.035 (3)	0.020 (3)	−0.001 (2)	0.000 (2)	0.009 (2)
C14	0.024 (3)	0.029 (3)	0.013 (2)	0.000 (2)	−0.002 (2)	0.007 (2)
C15	0.018 (3)	0.022 (3)	0.017 (2)	−0.001 (2)	−0.002 (2)	0.002 (2)

Cl1—C4	1.747 (5)	C1—C6	1.403 (6)
O1—C1	1.365 (6)	C2—C3	1.371 (7)
O1—H1	0.8400	C2—H2A	0.9500
O2—C9	1.247 (6)	C3—C4	1.395 (7)
O3—C12	1.371 (6)	C3—H3A	0.9500
O3—H3	0.8400	C4—C5	1.376 (7)
O4—C13	1.361 (6)	C5—C6	1.403 (7)
O4—H4	0.8400	C5—H5A	0.9500
O5—C14	1.366 (6)	C6—C7	1.450 (7)
O5—H5	0.8400	C7—H7	0.9500
O1w—H11	0.8347	C9—C10	1.474 (7)
O1w—H12	0.8378	C10—C11	1.384 (7)
O2w—H21	0.8421	C10—C15	1.408 (7)
O2w—H22	0.8400	C11—C12	1.377 (7)
N1—C7	1.283 (6)	C11—H11A	0.9500
N1—N2	1.386 (6)	C12—C13	1.395 (8)
N2—C9	1.350 (6)	C13—C14	1.394 (7)
N2—H2	0.8800	C14—C15	1.385 (7)
C1—C2	1.384 (7)	C15—H15	0.9500

C1—O1—H1	109.5	C1—C6—C7	122.9 (4)
C12—O3—H3	109.5	C5—C6—C7	118.3 (4)
C13—O4—H4	109.5	N1—C7—C6	121.0 (4)
C14—O5—H5	109.5	N1—C7—H7	119.5
H11—O1w—H12	110.0	C6—C7—H7	119.5
H21—O2w—H22	109.0	O2—C9—N2	122.2 (4)
C7—N1—N2	115.9 (4)	O2—C9—C10	122.6 (4)
C9—N2—N1	121.2 (4)	N2—C9—C10	115.1 (4)
C9—N2—H2	119.4	C11—C10—C15	120.3 (5)
N1—N2—H2	119.4	C11—C10—C9	119.7 (4)
O1—C1—C2	118.6 (4)	C15—C10—C9	119.9 (4)
O1—C1—C6	121.4 (4)	C12—C11—C10	120.0 (5)
C2—C1—C6	120.0 (4)	C12—C11—H11A	120.0
C3—C2—C1	121.2 (5)	C10—C11—H11A	120.0
C3—C2—H2A	119.4	O3—C12—C11	119.0 (5)
C1—C2—H2A	119.4	O3—C12—C13	120.5 (5)
C2—C3—C4	119.0 (5)	C11—C12—C13	120.5 (5)
C2—C3—H3A	120.5	O4—C13—C14	123.5 (5)
C4—C3—H3A	120.5	O4—C13—C12	116.8 (5)
C5—C4—C3	121.1 (5)	C14—C13—C12	119.7 (5)
C5—C4—Cl1	119.4 (4)	O5—C14—C15	123.4 (4)
C3—C4—Cl1	119.5 (4)	O5—C14—C13	116.2 (4)
C4—C5—C6	119.9 (4)	C15—C14—C13	120.3 (5)
C4—C5—H5A	120.0	C14—C15—C10	119.2 (4)
C6—C5—H5A	120.0	C14—C15—H15	120.4
C1—C6—C5	118.8 (5)	C10—C15—H15	120.4

C7—N1—N2—C9	−166.9 (5)	N2—C9—C10—C11	154.5 (5)
O1—C1—C2—C3	−180.0 (5)	O2—C9—C10—C15	148.7 (5)
C6—C1—C2—C3	−1.1 (8)	N2—C9—C10—C15	−29.5 (7)
C1—C2—C3—C4	1.0 (8)	C15—C10—C11—C12	−0.4 (8)
C2—C3—C4—C5	−0.6 (8)	C9—C10—C11—C12	175.6 (5)
C2—C3—C4—Cl1	178.0 (4)	C10—C11—C12—O3	−179.3 (5)
C3—C4—C5—C6	0.2 (8)	C10—C11—C12—C13	−1.2 (8)
Cl1—C4—C5—C6	−178.4 (4)	O3—C12—C13—O4	−0.1 (8)
O1—C1—C6—C5	179.6 (5)	C11—C12—C13—O4	−178.2 (5)
C2—C1—C6—C5	0.7 (7)	O3—C12—C13—C14	179.2 (5)
O1—C1—C6—C7	1.2 (8)	C11—C12—C13—C14	1.1 (8)
C2—C1—C6—C7	−177.7 (5)	O4—C13—C14—O5	1.3 (8)
C4—C5—C6—C1	−0.3 (7)	C12—C13—C14—O5	−178.0 (5)
C4—C5—C6—C7	178.2 (5)	O4—C13—C14—C15	179.9 (5)
N2—N1—C7—C6	176.3 (4)	C12—C13—C14—C15	0.6 (8)
C1—C6—C7—N1	−0.1 (8)	O5—C14—C15—C10	176.3 (5)
C5—C6—C7—N1	−178.5 (5)	C13—C14—C15—C10	−2.2 (8)
N1—N2—C9—O2	−13.1 (8)	C11—C10—C15—C14	2.1 (7)
N1—N2—C9—C10	165.1 (4)	C9—C10—C15—C14	−173.9 (5)
O2—C9—C10—C11	−27.4 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.89	2.631 (5)	146
O3—H3···O1wⁱ	0.84	1.96	2.737 (6)	153
O4—H4···O1wⁱⁱ	0.84	1.80	2.599 (7)	158
O5—H5···O2ⁱⁱ	0.84	1.93	2.765 (5)	171
O1w—H11···O3	0.83	2.28	2.969 (6)	140
O1w—H12···O4ⁱⁱⁱ	0.84	2.07	2.900 (7)	170
O2w—H21···O1	0.84	2.15	2.946 (5)	157
O2w—H22···O2^iv	0.84	1.97	2.808 (5)	172
N2—H2···O2wⁱⁱ	0.88	2.03	2.882 (5)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84	1.89	2.631 (5)	146
O3—H3⋯O1wⁱ	0.84	1.96	2.737 (6)	153
O4—H4⋯O1wⁱⁱ	0.84	1.80	2.599 (7)	158
O5—H5⋯O2ⁱⁱ	0.84	1.93	2.765 (5)	171
O1w—H11⋯O3	0.83	2.28	2.969 (6)	140
O1w—H12⋯O4ⁱⁱⁱ	0.84	2.07	2.900 (7)	170
O2w—H21⋯O1	0.84	2.15	2.946 (5)	157
O2w—H22⋯O2^iv	0.84	1.97	2.808 (5)	172
N2—H2⋯O2wⁱⁱ	0.88	2.03	2.882 (5)	162

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

1 in total

1. A short history of SHELX.

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

1 in total

1. N'-[1-(5-Bromo-2-hydroxy-phen-yl)ethyl-idene]-3,4,5-trihydroxy-benzohydrazide dimethyl sulfoxide solvate trihydrate.

Authors: Nura Suleiman Gwaram; Hamid Khaledi; Hapipah Mohd Ali; Ward T Robinson; Mahmood A Abdulla
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-02-27

1 in total