Literature DB >> 24426988

Di-μ-chlorido-bis-[(2-amino-benzamide-κ(2) N (2),O)chlorido-copper(II)].

Maamar Damous¹, George Dénès², Sofiane Bouacida³, Meriem Hamlaoui¹, Hocine Merazig¹, Jean-Claude Daran⁴.

Abstract

The title compound, [Cu2Cl4(C7H8N2O)2], crystallizes as discrete [CuLCl2]2 (L = 2-amino-benzamide) dimers with inversion symmetry. Each Cu(II) ion is five-coordinated and is bound to two bridging chloride ligands, a terminal chloride ligand and a bidentate 2-amino-benzamide ligand. The crystal structure exhibits alternating layers parallel to (010) along the b-axis direction. In the crystal, the components are linked via N-H⋯Cl hydrogen bonds, forming a three-dimensional network. These inter-actions link the mol-ecules within the layers and also link the layers together and reinforce the cohesion of the structure.

Entities: Chemical Disease Species

Year: 2013 PMID： 24426988 PMCID： PMC3884402 DOI： 10.1107/S1600536813021879

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

Related literature

For general background to 2-aminobenzamide derivatives, see: Nagaoka et al. (2006 ▶); Butsch et al. (2011 ▶); Kapoor et al. (2010 ▶). For related structures, see: Yang et al. (2012 ▶); Lah et al. (2006 ▶). For standard bond lengths, see: Allen (2002 ▶)

Experimental

Crystal data

[Cu2Cl4(C7H8N2O)2] M = 541.21 Monoclinic, a = 8.1888 (5) Å b = 13.8545 (6) Å c = 8.1592 (4) Å β = 98.771 (5)° V = 914.85 (8) Å3 Z = 2 Mo Kα radiation μ = 2.93 mm−1 T = 180 K 0.15 × 0.13 × 0.12 mm

Data collection

Agilent Xcalibur (Sapphire1) diffractometer Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.699, T max = 1 5578 measured reflections 2058 independent reflections 1897 reflections with I > 2σ(I) R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.022 wR(F 2) = 0.058 S = 1.04 2058 reflections 118 parameters H-atom parameters constrained Δρmax = 0.41 e Å−3 Δρmin = −0.41 e Å−3 Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶). Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813021879/hg5337sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021879/hg5337Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu₂Cl₄(C₇H₈N₂O)₂]	F(000) = 540
M_r = 541.21	D_x = 1.965 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3363 reflections
a = 8.1888 (5) Å	θ = 2.9–28.2°
b = 13.8545 (6) Å	µ = 2.93 mm⁻¹
c = 8.1592 (4) Å	T = 180 K
β = 98.771 (5)°	Cube, green
V = 914.85 (8) Å³	0.15 × 0.13 × 0.12 mm
Z = 2

Agilent Xcalibur (Sapphire1) diffractometer	2058 independent reflections
Radiation source: fine-focus sealed tube	1897 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 8.2632 pixels mm^-1	θ_max = 28.3°, θ_min = 2.9°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −17→18
T_min = 0.699, T_max = 1	l = −10→10
5578 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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.058	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0307P)² + 0.3739P] where P = (F_o² + 2F_c²)/3
2058 reflections	(Δ/σ)_max = 0.003
118 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Experimental. Absorption correction: empirical using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm CrysAlis PRO (Agilent, 2011).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Cu1	0.18491 (3)	−0.04957 (2)	0.58700 (3)	0.0126 (1)
Cl1	0.05270 (6)	0.10533 (3)	0.57135 (6)	0.0161 (1)
Cl2	0.36324 (6)	−0.12970 (3)	0.44121 (6)	0.0162 (1)
O1	0.15024 (17)	−0.13480 (9)	0.79155 (16)	0.0156 (4)
N1	0.37924 (19)	−0.00155 (11)	0.74251 (18)	0.0126 (4)
N2	0.1556 (2)	−0.16908 (11)	1.0607 (2)	0.0180 (5)
C1	0.2398 (2)	−0.00937 (12)	0.9884 (2)	0.0107 (5)
C2	0.3341 (2)	0.04226 (12)	0.8882 (2)	0.0111 (5)
C3	0.3819 (2)	0.13689 (13)	0.9288 (2)	0.0147 (5)
C4	0.3337 (3)	0.18053 (13)	1.0665 (2)	0.0181 (5)
C5	0.2408 (3)	0.13070 (13)	1.1664 (2)	0.0171 (5)
C6	0.1958 (2)	0.03556 (13)	1.1275 (2)	0.0140 (5)
C7	0.1801 (2)	−0.10930 (12)	0.9406 (2)	0.0122 (5)
H1A	0.43529	0.04286	0.68835	0.0152*
H1B	0.44964	−0.05231	0.77350	0.0152*
H2A	0.11781	−0.22765	1.03652	0.0216*
H2B	0.17697	−0.15031	1.16476	0.0216*
H3	0.44744	0.17143	0.86209	0.0176*
H4	0.36477	0.24546	1.09246	0.0217*
H5	0.20810	0.16101	1.26070	0.0206*
H6	0.13389	0.00073	1.19728	0.0168*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0105 (1)	0.0152 (1)	0.0119 (1)	0.0003 (1)	0.0005 (1)	−0.0027 (1)
Cl1	0.0141 (2)	0.0125 (2)	0.0198 (2)	0.0006 (2)	−0.0036 (2)	−0.0023 (2)
Cl2	0.0160 (2)	0.0175 (2)	0.0162 (2)	0.0013 (2)	0.0059 (2)	−0.0026 (2)
O1	0.0214 (7)	0.0129 (6)	0.0121 (6)	−0.0036 (5)	0.0016 (5)	−0.0002 (5)
N1	0.0118 (7)	0.0148 (7)	0.0119 (7)	−0.0002 (6)	0.0038 (6)	0.0005 (6)
N2	0.0280 (10)	0.0118 (7)	0.0140 (8)	−0.0036 (7)	0.0026 (7)	−0.0001 (6)
C1	0.0100 (8)	0.0100 (8)	0.0113 (8)	0.0013 (7)	−0.0007 (7)	0.0004 (7)
C2	0.0084 (8)	0.0147 (8)	0.0094 (8)	0.0021 (7)	−0.0011 (7)	0.0005 (7)
C3	0.0141 (9)	0.0149 (8)	0.0146 (9)	−0.0020 (7)	0.0009 (7)	0.0026 (7)
C4	0.0193 (10)	0.0124 (8)	0.0217 (10)	−0.0016 (7)	0.0004 (8)	−0.0032 (7)
C5	0.0177 (10)	0.0176 (9)	0.0162 (9)	0.0016 (8)	0.0030 (8)	−0.0049 (7)
C6	0.0118 (9)	0.0167 (9)	0.0135 (9)	0.0006 (7)	0.0022 (7)	0.0026 (7)
C7	0.0103 (9)	0.0127 (8)	0.0135 (9)	0.0016 (7)	0.0018 (7)	0.0014 (7)

Cu1—Cl1	2.3983 (5)	C1—C2	1.403 (2)
Cu1—Cl2	2.3043 (6)	C1—C6	1.389 (2)
Cu1—O1	2.0988 (13)	C1—C7	1.500 (2)
Cu1—N1	1.9923 (15)	C2—C3	1.394 (2)
Cu1—Cl1ⁱ	2.2990 (6)	C3—C4	1.385 (2)
O1—C7	1.254 (2)	C4—C5	1.382 (3)
N1—C2	1.433 (2)	C5—C6	1.392 (3)
N2—C7	1.322 (2)	C3—H3	0.9500
N1—H1A	0.9200	C4—H4	0.9500
N1—H1B	0.9200	C5—H5	0.9500
N2—H2A	0.8800	C6—H6	0.9500
N2—H2B	0.8800

Cl1—Cu1—Cl2	136.06 (2)	C2—C1—C6	118.81 (15)
Cl1—Cu1—O1	115.54 (4)	C2—C1—C7	120.37 (14)
Cl1—Cu1—N1	92.60 (5)	C6—C1—C7	120.74 (15)
Cl1—Cu1—Cl1ⁱ	86.23 (2)	N1—C2—C1	120.14 (15)
Cl2—Cu1—O1	108.22 (4)	N1—C2—C3	119.81 (15)
Cl2—Cu1—N1	88.98 (5)	C1—C2—C3	120.04 (15)
Cl1ⁱ—Cu1—Cl2	95.55 (2)	C2—C3—C4	119.93 (16)
O1—Cu1—N1	82.72 (6)	C3—C4—C5	120.73 (17)
Cl1ⁱ—Cu1—O1	93.00 (4)	C4—C5—C6	119.28 (16)
Cl1ⁱ—Cu1—N1	174.57 (5)	C1—C6—C5	121.19 (16)
Cu1—Cl1—Cu1ⁱ	93.77 (2)	O1—C7—C1	121.32 (15)
Cu1—O1—C7	125.63 (11)	N2—C7—C1	117.78 (15)
Cu1—N1—C2	112.82 (11)	O1—C7—N2	120.88 (16)
C2—N1—H1A	109.00	C2—C3—H3	120.00
C2—N1—H1B	109.00	C4—C3—H3	120.00
H1A—N1—H1B	108.00	C3—C4—H4	120.00
Cu1—N1—H1A	109.00	C5—C4—H4	120.00
Cu1—N1—H1B	109.00	C4—C5—H5	120.00
H2A—N2—H2B	120.00	C6—C5—H5	120.00
C7—N2—H2A	120.00	C1—C6—H6	119.00
C7—N2—H2B	120.00	C5—C6—H6	119.00

Cl2—Cu1—Cl1—Cu1ⁱ	94.09 (3)	Cu1—N1—C2—C1	55.55 (18)
O1—Cu1—Cl1—Cu1ⁱ	−91.53 (5)	C6—C1—C2—N1	−179.03 (15)
N1—Cu1—Cl1—Cu1ⁱ	−174.69 (5)	C7—C1—C6—C5	−175.43 (17)
Cl1ⁱ—Cu1—Cl1—Cu1ⁱ	0.00 (4)	C2—C1—C7—O1	−29.6 (2)
Cl1—Cu1—Cl1ⁱ—Cu1ⁱ	0.00 (4)	C6—C1—C2—C3	0.0 (2)
Cl2—Cu1—Cl1ⁱ—Cu1ⁱ	−135.94 (2)	C6—C1—C7—O1	147.06 (17)
O1—Cu1—Cl1ⁱ—Cu1ⁱ	115.41 (4)	C6—C1—C7—N2	−31.2 (2)
Cl1—Cu1—O1—C7	−53.92 (15)	C2—C1—C7—N2	152.19 (16)
Cl2—Cu1—O1—C7	121.99 (14)	C2—C1—C6—C5	1.3 (3)
N1—Cu1—O1—C7	35.49 (15)	C7—C1—C2—C3	176.68 (15)
Cl1ⁱ—Cu1—O1—C7	−141.17 (14)	C7—C1—C2—N1	−2.3 (2)
Cl1—Cu1—N1—C2	55.31 (11)	C1—C2—C3—C4	−1.2 (3)
Cl2—Cu1—N1—C2	−168.63 (11)	N1—C2—C3—C4	177.83 (17)
O1—Cu1—N1—C2	−60.11 (11)	C2—C3—C4—C5	1.2 (3)
Cu1—O1—C7—C1	2.6 (2)	C3—C4—C5—C6	0.1 (3)
Cu1—O1—C7—N2	−179.23 (12)	C4—C5—C6—C1	−1.3 (3)
Cu1—N1—C2—C3	−123.45 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl2ⁱⁱ	0.9200	2.4100	3.3113 (16)	166.00
N2—H2A···Cl1ⁱⁱⁱ	0.8800	2.7800	3.6439 (16)	169.00
N2—H2B···Cl2^iv	0.8800	2.5400	3.3493 (17)	153.00

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl2ⁱ	0.9200	2.4100	3.3113 (16)	166.00
N2—H2A⋯Cl1ⁱⁱ	0.8800	2.7800	3.6439 (16)	169.00
N2—H2B⋯Cl2ⁱⁱⁱ	0.8800	2.5400	3.3493 (17)	153.00

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

4 in total

1. The Cambridge Structural Database: a quarter of a million crystal structures and rising.

Authors: Frank H Allen
Journal: Acta Crystallogr B Date: 2002-05-29

2. Synthesis and cancer antiproliferative activity of new histone deacetylase inhibitors: hydrophilic hydroxamates and 2-aminobenzamide-containing derivatives.

Authors: Y Nagaoka; T Maeda; Y Kawai; D Nakashima; T Oikawa; K Shimoke; T Ikeuchi; H Kuwajima; S Uesato
Journal: Eur J Med Chem Date: 2006-04-11 Impact factor: 6.514

3. A short history of SHELX.

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

4. Anti-herpes simplex virus efficacies of 2-aminobenzamide derivatives as novel HSP90 inhibitors.

Authors: Yang-Fei Xiang; Chui-Wen Qian; Guo-Wen Xing; Jing Hao; Min Xia; Yi-Fei Wang
Journal: Bioorg Med Chem Lett Date: 2012-05-26 Impact factor: 2.823