Literature DB >> 21582612

N'-(3-Bromo-5-chloro-2-hydroxy-benzyl-idene)-3,4,5-trihydroxy-benzohydrazide methanol solvate.

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

Abstract

The benzohydrazide mol-ecule of the title compound, C(14)H(10)BrClN(2)O(5)·CH(3)OH, is non-planar, the two aromatic rings at either side of the -C(=O)-NH-N=CH- unit being twisted by 5.9 (1)°. The benzohydrazide mol-ecule is linked to the solvent mol-ecule by an O-H⋯O hydrogen bond. Mol-ecules are connected by further O-H⋯O hydrogen bonds and an N-H⋯O link into a two-dimensional array.

Entities: Chemical Disease Gene

Year: 2009 PMID： 21582612 PMCID： PMC2968970 DOI： 10.1107/S1600536809010575

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

C14H10BrClN2O5·CH4O M = 433.64 Monoclinic, a = 21.6157 (3) Å b = 12.7408 (2) Å c = 17.0803 (2) Å β = 136.641 (1)° V = 3229.57 (8) Å3 Z = 8 Mo Kα radiation μ = 2.75 mm−1 T = 123 K 0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.610, T max = 0.771 15301 measured reflections 3714 independent reflections 3407 reflections with I > 2σ(I) R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.023 wR(F 2) = 0.068 S = 1.03 3714 reflections 251 parameters 6 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.43 e Å−3 Δρmin = −0.35 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/S1600536809010575/tk2400sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010575/tk2400Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₀BrClN₂O₅·CH₄O	F(000) = 1744
M_r = 433.64	D_x = 1.784 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8789 reflections
a = 21.6157 (3) Å	θ = 2.7–28.3°
b = 12.7408 (2) Å	µ = 2.75 mm⁻¹
c = 17.0803 (2) Å	T = 123 K
β = 136.641 (1)°	Polyhedral, tan
V = 3229.57 (8) Å³	0.20 × 0.15 × 0.10 mm
Z = 8

Bruker SMART APEX diffractometer	3714 independent reflections
Radiation source: fine-focus sealed tube	3407 reflections with I > 2σ(I)
graphite	R_int = 0.016
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→26
T_min = 0.610, T_max = 0.771	k = −16→16
15301 measured reflections	l = −22→21

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.068	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0429P)² + 3.4447P] where P = (F_o² + 2F_c²)/3
3714 reflections	(Δ/σ)_max = 0.001
251 parameters	Δρ_max = 0.43 e Å⁻³
6 restraints	Δρ_min = −0.35 e Å⁻³

	x	y	z	U_iso*/U_eq
Br1	0.044783 (12)	0.783092 (13)	0.137916 (14)	0.02172 (7)
Cl1	0.01420 (3)	0.35175 (3)	0.10946 (4)	0.02369 (10)
N1	0.18779 (9)	0.61375 (11)	0.54542 (11)	0.0148 (3)
N2	0.23179 (9)	0.58418 (11)	0.65407 (11)	0.0154 (3)
O1	0.13116 (9)	0.74001 (9)	0.37133 (11)	0.0211 (3)
O2	0.20939 (8)	0.74133 (9)	0.69379 (10)	0.0187 (2)
O3	0.36037 (9)	0.69205 (10)	1.09583 (10)	0.0219 (3)
O4	0.37603 (8)	0.47725 (9)	1.12740 (10)	0.0189 (2)
O5	0.31633 (9)	0.34724 (9)	0.95863 (10)	0.0205 (3)
O6	0.15053 (8)	0.88367 (9)	0.75713 (10)	0.0196 (2)
C1	0.10878 (11)	0.64859 (12)	0.31698 (13)	0.0155 (3)
C2	0.06644 (11)	0.65171 (12)	0.20499 (14)	0.0156 (3)
C3	0.03858 (11)	0.56163 (13)	0.14173 (13)	0.0172 (3)
H3A	0.0088	0.5655	0.0652	0.021*
C4	0.05469 (11)	0.46540 (12)	0.19171 (14)	0.0168 (3)
C5	0.09940 (10)	0.45814 (12)	0.30364 (13)	0.0158 (3)
H5A	0.1117	0.3914	0.3373	0.019*
C6	0.12644 (10)	0.54979 (12)	0.36718 (13)	0.0151 (3)
C7	0.17192 (10)	0.53678 (12)	0.48399 (13)	0.0155 (3)
H7	0.1907	0.4684	0.5163	0.019*
C8	0.23645 (10)	0.64897 (12)	0.72065 (13)	0.0147 (3)
C9	0.27436 (10)	0.60244 (12)	0.82779 (13)	0.0143 (3)
C10	0.30257 (11)	0.66835 (12)	0.91445 (13)	0.0161 (3)
H10	0.2997	0.7424	0.9056	0.019*
C11	0.33473 (11)	0.62583 (12)	1.01356 (13)	0.0156 (3)
C12	0.34227 (10)	0.51690 (12)	1.02835 (13)	0.0146 (3)
C13	0.31234 (10)	0.45163 (12)	0.94055 (13)	0.0147 (3)
C14	0.27745 (10)	0.49359 (12)	0.84020 (13)	0.0146 (3)
H14	0.2557	0.4486	0.7800	0.018*
C15	0.06333 (12)	0.92150 (14)	0.65359 (15)	0.0237 (4)
H15A	0.0445	0.9781	0.6715	0.036*
H15B	0.0196	0.8640	0.6160	0.036*
H15C	0.0664	0.9482	0.6027	0.036*
H1	0.154 (2)	0.731 (3)	0.4365 (15)	0.087 (13)*
H3	0.3635 (18)	0.6613 (19)	1.1413 (18)	0.044 (7)*
H4	0.3783 (17)	0.4119 (8)	1.129 (2)	0.036 (7)*
H5	0.3065 (15)	0.3125 (16)	0.9101 (15)	0.030 (6)*
H6	0.1634 (16)	0.8331 (14)	0.741 (2)	0.037 (7)*
H2	0.2604 (14)	0.5242 (11)	0.6799 (18)	0.029 (6)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02904 (11)	0.01747 (10)	0.01845 (10)	0.00031 (6)	0.01720 (9)	0.00285 (6)
Cl1	0.0373 (2)	0.01580 (19)	0.01895 (19)	−0.00382 (16)	0.02079 (19)	−0.00522 (14)
N1	0.0169 (6)	0.0172 (6)	0.0109 (6)	0.0006 (5)	0.0103 (5)	0.0013 (5)
N2	0.0205 (6)	0.0142 (6)	0.0119 (6)	0.0032 (5)	0.0120 (6)	0.0031 (5)
O1	0.0321 (7)	0.0152 (5)	0.0161 (6)	0.0006 (5)	0.0175 (6)	−0.0016 (5)
O2	0.0293 (6)	0.0135 (5)	0.0186 (6)	0.0039 (5)	0.0191 (5)	0.0034 (4)
O3	0.0374 (7)	0.0154 (5)	0.0171 (6)	−0.0039 (5)	0.0212 (6)	−0.0038 (5)
O4	0.0294 (6)	0.0154 (6)	0.0142 (5)	0.0022 (5)	0.0166 (5)	0.0019 (4)
O5	0.0378 (7)	0.0109 (5)	0.0182 (6)	0.0028 (5)	0.0221 (6)	0.0017 (4)
O6	0.0251 (6)	0.0178 (6)	0.0186 (6)	0.0016 (5)	0.0168 (5)	−0.0013 (5)
C1	0.0184 (7)	0.0151 (7)	0.0154 (7)	−0.0006 (6)	0.0131 (7)	−0.0020 (6)
C2	0.0186 (7)	0.0153 (7)	0.0153 (7)	0.0015 (6)	0.0130 (7)	0.0026 (6)
C3	0.0185 (7)	0.0226 (8)	0.0135 (7)	−0.0012 (6)	0.0126 (7)	−0.0011 (6)
C4	0.0202 (7)	0.0170 (7)	0.0169 (7)	−0.0017 (6)	0.0147 (7)	−0.0037 (6)
C5	0.0184 (7)	0.0153 (7)	0.0164 (7)	0.0005 (6)	0.0136 (6)	0.0007 (6)
C6	0.0164 (7)	0.0182 (7)	0.0129 (7)	0.0004 (6)	0.0113 (6)	0.0003 (6)
C7	0.0173 (7)	0.0156 (7)	0.0135 (7)	0.0006 (6)	0.0112 (6)	0.0017 (6)
C8	0.0165 (7)	0.0151 (7)	0.0138 (7)	−0.0016 (6)	0.0114 (6)	−0.0007 (5)
C9	0.0158 (7)	0.0158 (7)	0.0126 (7)	0.0010 (6)	0.0107 (6)	0.0009 (6)
C10	0.0212 (8)	0.0123 (7)	0.0166 (8)	−0.0005 (6)	0.0144 (7)	−0.0003 (6)
C11	0.0198 (7)	0.0148 (7)	0.0140 (7)	−0.0021 (6)	0.0129 (6)	−0.0030 (6)
C12	0.0168 (7)	0.0167 (7)	0.0123 (7)	0.0009 (6)	0.0112 (6)	0.0013 (6)
C13	0.0180 (7)	0.0121 (7)	0.0168 (7)	0.0016 (6)	0.0136 (6)	0.0006 (6)
C14	0.0189 (7)	0.0136 (7)	0.0144 (7)	0.0005 (6)	0.0131 (6)	−0.0005 (5)
C15	0.0247 (8)	0.0219 (8)	0.0214 (8)	0.0000 (7)	0.0158 (7)	−0.0015 (7)

Br1—C2	1.8852 (15)	C3—C4	1.386 (2)
Cl1—C4	1.7460 (16)	C3—H3A	0.9500
N1—C7	1.287 (2)	C4—C5	1.382 (2)
N1—N2	1.3870 (18)	C5—C6	1.400 (2)
N2—C8	1.348 (2)	C5—H5A	0.9500
N2—H2	0.874 (10)	C6—C7	1.457 (2)
O1—C1	1.3415 (19)	C7—H7	0.9500
O1—H1	0.832 (10)	C8—C9	1.480 (2)
O2—C8	1.2438 (19)	C9—C14	1.397 (2)
O3—C11	1.3642 (19)	C9—C10	1.398 (2)
O3—H3	0.828 (10)	C10—C11	1.390 (2)
O4—C12	1.3619 (18)	C10—H10	0.9500
O4—H4	0.833 (10)	C11—C12	1.399 (2)
O5—C13	1.3538 (18)	C12—C13	1.396 (2)
O5—H5	0.820 (10)	C13—C14	1.383 (2)
O6—C15	1.437 (2)	C14—H14	0.9500
O6—H6	0.828 (10)	C15—H15A	0.9800
C1—C2	1.397 (2)	C15—H15B	0.9800
C1—C6	1.410 (2)	C15—H15C	0.9800
C2—C3	1.379 (2)

C7—N1—N2	113.63 (13)	C6—C7—H7	118.5
C8—N2—N1	121.35 (13)	O2—C8—N2	122.77 (14)
C8—N2—H2	121.2 (15)	O2—C8—C9	121.61 (14)
N1—N2—H2	117.2 (15)	N2—C8—C9	115.61 (13)
C1—O1—H1	112 (3)	C14—C9—C10	119.97 (14)
C11—O3—H3	111.6 (19)	C14—C9—C8	120.49 (14)
C12—O4—H4	112.6 (18)	C10—C9—C8	119.44 (14)
C13—O5—H5	111.9 (17)	C11—C10—C9	120.15 (14)
C15—O6—H6	107.8 (17)	C11—C10—H10	119.9
O1—C1—C2	118.05 (14)	C9—C10—H10	119.9
O1—C1—C6	123.52 (14)	O3—C11—C10	118.85 (14)
C2—C1—C6	118.42 (14)	O3—C11—C12	121.39 (14)
C3—C2—C1	121.82 (14)	C10—C11—C12	119.75 (14)
C3—C2—Br1	119.27 (12)	O4—C12—C13	121.65 (14)
C1—C2—Br1	118.90 (12)	O4—C12—C11	118.63 (14)
C2—C3—C4	118.86 (14)	C13—C12—C11	119.67 (14)
C2—C3—H3A	120.6	O5—C13—C14	123.32 (14)
C4—C3—H3A	120.6	O5—C13—C12	115.94 (14)
C5—C4—C3	121.40 (14)	C14—C13—C12	120.69 (14)
C5—C4—Cl1	119.65 (12)	C13—C14—C9	119.64 (14)
C3—C4—Cl1	118.92 (12)	C13—C14—H14	120.2
C4—C5—C6	119.62 (14)	C9—C14—H14	120.2
C4—C5—H5A	120.2	O6—C15—H15A	109.5
C6—C5—H5A	120.2	O6—C15—H15B	109.5
C5—C6—C1	119.81 (14)	H15A—C15—H15B	109.5
C5—C6—C7	116.89 (14)	O6—C15—H15C	109.5
C1—C6—C7	123.30 (14)	H15A—C15—H15C	109.5
N1—C7—C6	122.97 (14)	H15B—C15—H15C	109.5
N1—C7—H7	118.5

C7—N1—N2—C8	−165.52 (15)	N1—N2—C8—C9	172.04 (14)
O1—C1—C2—C3	−177.88 (15)	O2—C8—C9—C14	159.38 (15)
C6—C1—C2—C3	2.7 (2)	N2—C8—C9—C14	−19.4 (2)
O1—C1—C2—Br1	0.8 (2)	O2—C8—C9—C10	−17.1 (2)
C6—C1—C2—Br1	−178.63 (11)	N2—C8—C9—C10	164.18 (15)
C1—C2—C3—C4	−1.2 (2)	C14—C9—C10—C11	0.8 (2)
Br1—C2—C3—C4	−179.92 (12)	C8—C9—C10—C11	177.25 (14)
C2—C3—C4—C5	−1.3 (2)	C9—C10—C11—O3	−178.92 (15)
C2—C3—C4—Cl1	176.64 (12)	C9—C10—C11—C12	2.6 (2)
C3—C4—C5—C6	2.2 (2)	O3—C11—C12—O4	0.0 (2)
Cl1—C4—C5—C6	−175.66 (12)	C10—C11—C12—O4	178.42 (14)
C4—C5—C6—C1	−0.7 (2)	O3—C11—C12—C13	177.72 (14)
C4—C5—C6—C7	179.02 (14)	C10—C11—C12—C13	−3.9 (2)
O1—C1—C6—C5	178.92 (15)	O4—C12—C13—O5	2.0 (2)
C2—C1—C6—C5	−1.7 (2)	C11—C12—C13—O5	−175.63 (14)
O1—C1—C6—C7	−0.8 (2)	O4—C12—C13—C14	179.35 (14)
C2—C1—C6—C7	178.61 (14)	C11—C12—C13—C14	1.7 (2)
N2—N1—C7—C6	−179.99 (14)	O5—C13—C14—C9	178.84 (15)
C5—C6—C7—N1	−169.07 (15)	C12—C13—C14—C9	1.7 (2)
C1—C6—C7—N1	10.7 (2)	C10—C9—C14—C13	−3.0 (2)
N1—N2—C8—O2	−6.7 (2)	C8—C9—C14—C13	−179.38 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5ⁱ	0.83 (1)	2.03 (3)	2.607 (2)	126 (3)
O3—H3···O6ⁱⁱ	0.83 (1)	2.05 (1)	2.856 (2)	165 (3)
O4—H4···O1ⁱⁱⁱ	0.83 (1)	2.20 (1)	3.027 (2)	173 (2)
O5—H5···O2ⁱⁱⁱ	0.82 (1)	1.79 (1)	2.608 (2)	176 (2)
O6—H6···O2	0.83 (1)	2.04 (1)	2.843 (2)	164 (2)
N2—H2···O6ⁱⁱⁱ	0.87 (1)	2.25 (1)	3.112 (2)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5ⁱ	0.83 (1)	2.03 (3)	2.607 (2)	126 (3)
O3—H3⋯O6ⁱⁱ	0.83 (1)	2.05 (1)	2.856 (2)	165 (3)
O4—H4⋯O1ⁱⁱⁱ	0.83 (1)	2.20 (1)	3.027 (2)	173 (2)
O5—H5⋯O2ⁱⁱⁱ	0.82 (1)	1.79 (1)	2.608 (2)	176 (2)
O6—H6⋯O2	0.83 (1)	2.04 (1)	2.843 (2)	164 (2)
N2—H2⋯O6ⁱⁱⁱ	0.87 (1)	2.25 (1)	3.112 (2)	169 (2)

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

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'-(2,4-Dimethoxy-benzyl-idene)-3,4,5-trihydroxy-benzohydrazide ethanol solvate.

Authors: Abeer A Alhadi; Siti Munirah Saharin; Hapipah Mohd Ali; Ward T Robinson; Mahmood A Abdulla
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-05-23

1 in total