[(E)-N′-(5-Chloro-2-oxidobenzyl­idene-κO)-3,4,5-trimeth­oxy­benzohydrazidato-κ2N′,O](pyridine-κN)copper(II)

Wang, Y.-M.; Lin, X.-H.; Chen, Z.; Jiang, H.-L.; Zhang, C.-J.

doi:10.1107/S1600536811009901

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page m526

doi:10.1107/S1600536811009901

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[(E)-N′-(5-Chloro-2-oxidobenzylidene-κO)-3,4,5-trimethoxybenzohydrazidato-κ²N′,O](pyridine-κN)copper(II)

Yu-Min Wang,^a ^* Xiao-Hui Lin,^a Zhen Chen,^a Hong-Li Jiang ^a and Chang-Jun Zhang ^a

^aSchool of Chemistry and Chemical Engineering, Taishan Medical University, Tai an 271016, People's Republic of China
^*Correspondence e-mail: minwangyu@126.com

(Received 7 March 2011; accepted 16 March 2011; online 7 April 2011)

In the title compound, [Cu(C₁₇H₁₅ClN₂O₅)(C₅H₅N)], the Cu^II atom is coordinated by one N atom and two O atoms from an anionic salicylaldehyde benzoylhydrazone ligand and one pyridine N atom in a distorted square-planar geometry. The bonds displays the usual elongation with mean Cu—O and Cu—N bond lengths of 1.926 and 1.976 Å, respectively. The pyridine ring makes dihedral angles of 26.12 (13) and 11.08 (12)°, respectively, with the trimethoxyphenyl and phenolate rings, which make a dihedral angle of 16.05 (12)° with one another.

Related literature

For the biolgical activity of salicylaldehyde derivatives, see: Chan et al. (1995 ); Ranford et al. (1998 ); Monfared et al. (2009 ). For related structures, see: Lee et al. (2003 ).

Experimental

Crystal data

[Cu(C₁₇H₁₅ClN₂O₅)(C₅H₅N)]
M_r = 505.40
Monoclinic, P 2₁ /n
a = 14.274 (4) Å
b = 7.5763 (18) Å
c = 20.753 (5) Å
β = 99.108 (4)°
V = 2216.1 (9) Å³
Z = 4
Mo Kα radiation
μ = 1.15 mm⁻¹
T = 298 K
0.19 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.812, T_max = 0.875
11265 measured reflections
3908 independent reflections
3184 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.086
S = 1.04
3908 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009901/jh2271sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009901/jh2271Isup2.hkl

checkCIF report

Comment top

Transition metal complexes with potential biological activity are the focus of extensive investigation. Salicylaldehyde benzoylhydrazone possess mild bacteriostatic activity and inhibits DNA synthesis and cell growth (Chan et al.; 1995). Salicylaldehyde acetylhydrazone displays radioprotective properties (Ranford et al.; 1998). Because of the biological interest in this type of chelate system, several structural studies have been carried out on copper with their analogues (Lee et al.; 2003). The copper(II) complex was shown to be significantly more potent than the metal-free chelate, leading to the suggestion that the metal complex was the biologically active species (Monfared et al.; 2009). We report here the crystal structure of the title compound, (I) (Fig. 1). It can be seen that the coordination environment of the copper atom consists of two oxygen atoms and one nitrogen atom from the salicylaldehyde benzoylhydrazone, and one nitrogen atom from the pyridine groups, making up a distorted square-planar environment. The bond length displays the usual elongation: Cu—O = 1.9256 (average) and Cu—N = 1.9755 (average). The pyridine ring makes dihedral angles of 26.12° and 11.08°, respectively, with the C9—C14 and C1—C6 phenyl rings. The C1—C6 benzene ring system makes a dihedral angle of 16.05° with the other C9—C14 benzene ring.

Related literature top

For the biolgical activity of salicylaldehyde derivatives, see: Chan et al. (1995); Ranford et al. (1998); Monfared et al. (2009). For related structures, see: Lee et al. (2003).

Experimental top

Mixture of 20 ml aqueous solution of copper (II) acetate (0.2 mmol) with 2 ml of pyridine was stirred with 20 ml e thanolic solution of (E)-N'-(5-chloro-2-hydroxybenzylidene) -3,4,5-trimethoxybenzohydrazide for 1 h. The resulted solution was leaved in dark place for evaporation. After 1 week of stating blue needle-like shape crystals were grown.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Packing diagram.

[(E)-N'-(5-Chloro-2-oxidobenzylidene-κO)-3,4,5- trimethoxybenzohydrazidato-κ²N',O](pyridine- κN)copper(II) top

Crystal data top

[Cu(C₁₇H₁₅ClN₂O₅)(C₅H₅N)]	F(000) = 1036
M_r = 505.40	D_x = 1.515 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3527 reflections
a = 14.274 (4) Å	θ = 2.9–25.3°
b = 7.5763 (18) Å	µ = 1.15 mm⁻¹
c = 20.753 (5) Å	T = 298 K
β = 99.108 (4)°	Block, blue
V = 2216.1 (9) Å³	0.19 × 0.16 × 0.12 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3908 independent reflections
Radiation source: fine-focus sealed tube	3184 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −15→17
T_min = 0.812, T_max = 0.875	k = −8→9
11265 measured reflections	l = −20→24

Refinement top

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0423P)² + 0.808P] where P = (F_o² + 2F_c²)/3
3908 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Cu(C₁₇H₁₅ClN₂O₅)(C₅H₅N)]	V = 2216.1 (9) Å³
M_r = 505.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.274 (4) Å	µ = 1.15 mm⁻¹
b = 7.5763 (18) Å	T = 298 K
c = 20.753 (5) Å	0.19 × 0.16 × 0.12 mm
β = 99.108 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3908 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3184 reflections with I > 2σ(I)
T_min = 0.812, T_max = 0.875	R_int = 0.027
11265 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.04	Δρ_max = 0.27 e Å⁻³
3908 reflections	Δρ_min = −0.37 e Å⁻³
289 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.54442 (2)	0.14856 (4)	0.056192 (13)	0.03244 (11)
Cl1	0.26557 (6)	0.62229 (10)	−0.21238 (3)	0.0569 (2)
O1	0.52842 (12)	0.1751 (2)	−0.03651 (8)	0.0393 (4)
O2	0.54254 (12)	0.1224 (2)	0.14894 (8)	0.0364 (4)
O3	0.5244 (2)	−0.0473 (3)	0.38634 (10)	0.0825 (8)
O4	0.41727 (15)	0.2050 (3)	0.42842 (8)	0.0565 (5)
O5	0.33613 (15)	0.4566 (3)	0.34986 (9)	0.0655 (6)
N1	0.67522 (14)	0.0438 (3)	0.05888 (9)	0.0324 (4)
N2	0.43295 (14)	0.2875 (3)	0.06254 (9)	0.0312 (4)
N3	0.40808 (14)	0.2968 (3)	0.12482 (9)	0.0352 (5)
C1	0.46948 (17)	0.2826 (3)	−0.07312 (11)	0.0337 (5)
C2	0.39692 (17)	0.3819 (3)	−0.04970 (11)	0.0315 (5)
C3	0.33515 (18)	0.4867 (3)	−0.09362 (12)	0.0370 (6)
H3	0.2878	0.5516	−0.0784	0.044*
C4	0.34372 (18)	0.4943 (3)	−0.15816 (12)	0.0386 (6)
C5	0.4148 (2)	0.3997 (3)	−0.18158 (12)	0.0421 (6)
H5	0.4209	0.4063	−0.2255	0.051*
C6	0.47585 (19)	0.2969 (3)	−0.13977 (12)	0.0399 (6)
H6	0.5231	0.2346	−0.1561	0.048*
C7	0.38229 (18)	0.3777 (3)	0.01742 (12)	0.0346 (6)
H7	0.3329	0.4448	0.0289	0.042*
C8	0.47163 (17)	0.2079 (3)	0.16524 (11)	0.0328 (5)
C9	0.45815 (17)	0.2063 (3)	0.23496 (11)	0.0333 (5)
C10	0.50005 (19)	0.0761 (4)	0.27666 (12)	0.0423 (6)
H10	0.5382	−0.0089	0.2615	0.051*
C11	0.4850 (2)	0.0729 (4)	0.34094 (12)	0.0464 (7)
C12	0.42910 (18)	0.2013 (4)	0.36393 (11)	0.0411 (6)
C13	0.38825 (18)	0.3340 (4)	0.32232 (12)	0.0410 (6)
C14	0.40278 (18)	0.3369 (3)	0.25749 (12)	0.0393 (6)
H14	0.3757	0.4253	0.2295	0.047*
C15	0.5491 (3)	−0.2135 (5)	0.36663 (18)	0.0856 (12)
H15A	0.4979	−0.2609	0.3360	0.128*
H15B	0.5616	−0.2899	0.4039	0.128*
H15C	0.6049	−0.2046	0.3464	0.128*
C16	0.3549 (3)	0.0777 (6)	0.44687 (19)	0.1005 (15)
H16A	0.2959	0.0819	0.4174	0.151*
H16B	0.3437	0.1018	0.4904	0.151*
H16C	0.3826	−0.0374	0.4454	0.151*
C17	0.2831 (3)	0.5821 (5)	0.30812 (17)	0.0887 (13)
H17A	0.3257	0.6550	0.2883	0.133*
H17B	0.2469	0.6545	0.3331	0.133*
H17C	0.2409	0.5216	0.2747	0.133*
C18	0.71659 (18)	0.0346 (4)	0.00516 (12)	0.0414 (6)
H18	0.6856	0.0849	−0.0332	0.050*
C19	0.80282 (19)	−0.0460 (4)	0.00440 (13)	0.0497 (7)
H19	0.8296	−0.0487	−0.0336	0.060*
C20	0.8487 (2)	−0.1221 (4)	0.06053 (14)	0.0481 (7)
H20	0.9064	−0.1793	0.0610	0.058*
C21	0.80784 (19)	−0.1126 (4)	0.11634 (13)	0.0447 (7)
H21	0.8378	−0.1629	0.1551	0.054*
C22	0.72216 (18)	−0.0276 (3)	0.11392 (12)	0.0368 (6)
H22	0.6957	−0.0192	0.1520	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.03527 (18)	0.03684 (19)	0.02615 (17)	0.00328 (13)	0.00780 (12)	0.00003 (12)
Cl1	0.0675 (5)	0.0611 (5)	0.0370 (4)	0.0104 (4)	−0.0071 (3)	0.0082 (3)
O1	0.0453 (11)	0.0446 (10)	0.0289 (9)	0.0119 (8)	0.0083 (8)	0.0031 (8)
O2	0.0374 (10)	0.0434 (10)	0.0296 (9)	0.0054 (8)	0.0092 (7)	−0.0010 (7)
O3	0.136 (2)	0.0742 (16)	0.0376 (12)	0.0460 (16)	0.0132 (13)	0.0155 (11)
O4	0.0654 (13)	0.0796 (14)	0.0270 (10)	−0.0020 (11)	0.0151 (9)	0.0004 (9)
O5	0.0726 (15)	0.0912 (16)	0.0354 (11)	0.0362 (13)	0.0167 (10)	−0.0040 (11)
N1	0.0345 (11)	0.0330 (11)	0.0300 (11)	−0.0024 (9)	0.0065 (9)	−0.0012 (9)
N2	0.0341 (11)	0.0341 (11)	0.0261 (10)	−0.0016 (9)	0.0071 (8)	0.0000 (9)
N3	0.0374 (12)	0.0442 (12)	0.0253 (10)	0.0027 (10)	0.0088 (9)	0.0001 (9)
C1	0.0393 (14)	0.0309 (13)	0.0310 (13)	−0.0036 (11)	0.0061 (10)	−0.0003 (11)
C2	0.0351 (13)	0.0283 (13)	0.0308 (13)	−0.0037 (10)	0.0044 (10)	0.0007 (10)
C3	0.0400 (15)	0.0337 (13)	0.0368 (14)	0.0004 (11)	0.0043 (11)	0.0005 (11)
C4	0.0484 (16)	0.0319 (13)	0.0321 (14)	−0.0032 (12)	−0.0038 (11)	0.0046 (11)
C5	0.0558 (17)	0.0419 (15)	0.0285 (13)	−0.0072 (13)	0.0063 (12)	0.0020 (11)
C6	0.0484 (16)	0.0393 (14)	0.0339 (14)	0.0017 (12)	0.0125 (12)	−0.0002 (11)
C7	0.0367 (14)	0.0347 (13)	0.0333 (13)	0.0020 (11)	0.0083 (11)	−0.0010 (11)
C8	0.0365 (14)	0.0342 (13)	0.0285 (12)	−0.0069 (11)	0.0076 (11)	−0.0035 (10)
C9	0.0328 (13)	0.0422 (14)	0.0255 (12)	−0.0041 (11)	0.0064 (10)	−0.0023 (11)
C10	0.0471 (16)	0.0467 (15)	0.0342 (14)	0.0078 (13)	0.0097 (12)	−0.0018 (12)
C11	0.0548 (18)	0.0527 (17)	0.0309 (14)	0.0034 (14)	0.0043 (12)	0.0055 (12)
C12	0.0426 (15)	0.0576 (17)	0.0242 (13)	−0.0049 (13)	0.0083 (11)	−0.0043 (12)
C13	0.0369 (14)	0.0573 (17)	0.0300 (13)	0.0056 (12)	0.0094 (11)	−0.0066 (12)
C14	0.0403 (15)	0.0478 (15)	0.0297 (13)	0.0050 (12)	0.0053 (11)	−0.0002 (11)
C15	0.110 (3)	0.072 (2)	0.075 (2)	0.030 (2)	0.018 (2)	0.024 (2)
C16	0.132 (4)	0.113 (3)	0.069 (3)	−0.036 (3)	0.056 (3)	0.000 (2)
C17	0.089 (3)	0.115 (3)	0.062 (2)	0.061 (3)	0.009 (2)	−0.010 (2)
C18	0.0392 (15)	0.0530 (16)	0.0325 (14)	0.0007 (12)	0.0073 (11)	0.0036 (12)
C19	0.0411 (16)	0.071 (2)	0.0405 (16)	0.0039 (14)	0.0158 (12)	−0.0036 (14)
C20	0.0358 (15)	0.0576 (18)	0.0512 (17)	0.0086 (13)	0.0082 (13)	−0.0046 (14)
C21	0.0419 (16)	0.0521 (17)	0.0387 (15)	0.0044 (13)	0.0016 (12)	0.0022 (12)
C22	0.0392 (14)	0.0402 (14)	0.0313 (13)	−0.0005 (11)	0.0065 (11)	−0.0015 (11)

Geometric parameters (Å, º) top

Cu1—O1	1.9119 (16)	C7—H7	0.9300
Cu1—N2	1.930 (2)	C8—C9	1.490 (3)
Cu1—O2	1.9394 (16)	C9—C10	1.384 (4)
Cu1—N1	2.021 (2)	C9—C14	1.393 (3)
Cl1—C4	1.747 (3)	C10—C11	1.385 (3)
O1—C1	1.321 (3)	C10—H10	0.9300
O2—C8	1.291 (3)	C11—C12	1.390 (4)
O3—C11	1.366 (3)	C12—C13	1.392 (4)
O3—C15	1.386 (4)	C13—C14	1.394 (3)
O4—C12	1.375 (3)	C14—H14	0.9300
O4—C16	1.406 (4)	C15—H15A	0.9600
O5—C13	1.370 (3)	C15—H15B	0.9600
O5—C17	1.421 (4)	C15—H15C	0.9600
N1—C22	1.343 (3)	C16—H16A	0.9600
N1—C18	1.344 (3)	C16—H16B	0.9600
N2—C7	1.285 (3)	C16—H16C	0.9600
N2—N3	1.395 (2)	C17—H17A	0.9600
N3—C8	1.319 (3)	C17—H17B	0.9600
C1—C6	1.405 (3)	C17—H17C	0.9600
C1—C2	1.426 (3)	C18—C19	1.376 (4)
C2—C3	1.408 (3)	C18—H18	0.9300
C2—C7	1.441 (3)	C19—C20	1.370 (4)
C3—C4	1.365 (3)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.378 (4)
C4—C5	1.391 (4)	C20—H20	0.9300
C5—C6	1.371 (4)	C21—C22	1.376 (4)
C5—H5	0.9300	C21—H21	0.9300
C6—H6	0.9300	C22—H22	0.9300

O1—Cu1—N2	92.45 (7)	C11—C10—H10	120.1
O1—Cu1—O2	172.44 (7)	O3—C11—C10	124.5 (3)
N2—Cu1—O2	81.20 (7)	O3—C11—C12	115.2 (2)
O1—Cu1—N1	91.82 (7)	C10—C11—C12	120.2 (2)
N2—Cu1—N1	168.60 (8)	O4—C12—C11	120.9 (2)
O2—Cu1—N1	95.18 (7)	O4—C12—C13	119.0 (2)
C1—O1—Cu1	127.39 (15)	C11—C12—C13	120.0 (2)
C8—O2—Cu1	110.09 (14)	O5—C13—C12	115.6 (2)
C11—O3—C15	119.9 (2)	O5—C13—C14	124.4 (2)
C12—O4—C16	115.6 (2)	C12—C13—C14	119.9 (2)
C13—O5—C17	118.1 (2)	C9—C14—C13	119.5 (2)
C22—N1—C18	117.3 (2)	C9—C14—H14	120.3
C22—N1—Cu1	121.05 (16)	C13—C14—H14	120.3
C18—N1—Cu1	121.52 (17)	O3—C15—H15A	109.5
C7—N2—N3	116.9 (2)	O3—C15—H15B	109.5
C7—N2—Cu1	127.97 (16)	H15A—C15—H15B	109.5
N3—N2—Cu1	115.09 (14)	O3—C15—H15C	109.5
C8—N3—N2	108.26 (19)	H15A—C15—H15C	109.5
O1—C1—C6	118.6 (2)	H15B—C15—H15C	109.5
O1—C1—C2	124.0 (2)	O4—C16—H16A	109.5
C6—C1—C2	117.3 (2)	O4—C16—H16B	109.5
C3—C2—C1	119.4 (2)	H16A—C16—H16B	109.5
C3—C2—C7	117.8 (2)	O4—C16—H16C	109.5
C1—C2—C7	122.8 (2)	H16A—C16—H16C	109.5
C4—C3—C2	121.0 (2)	H16B—C16—H16C	109.5
C4—C3—H3	119.5	O5—C17—H17A	109.5
C2—C3—H3	119.5	O5—C17—H17B	109.5
C3—C4—C5	120.3 (2)	H17A—C17—H17B	109.5
C3—C4—Cl1	120.5 (2)	O5—C17—H17C	109.5
C5—C4—Cl1	119.17 (19)	H17A—C17—H17C	109.5
C6—C5—C4	119.8 (2)	H17B—C17—H17C	109.5
C6—C5—H5	120.1	N1—C18—C19	122.9 (2)
C4—C5—H5	120.1	N1—C18—H18	118.5
C5—C6—C1	122.2 (2)	C19—C18—H18	118.5
C5—C6—H6	118.9	C20—C19—C18	119.0 (2)
C1—C6—H6	118.9	C20—C19—H19	120.5
N2—C7—C2	124.4 (2)	C18—C19—H19	120.5
N2—C7—H7	117.8	C19—C20—C21	119.0 (3)
C2—C7—H7	117.8	C19—C20—H20	120.5
O2—C8—N3	125.3 (2)	C21—C20—H20	120.5
O2—C8—C9	118.5 (2)	C22—C21—C20	119.0 (2)
N3—C8—C9	116.1 (2)	C22—C21—H21	120.5
C10—C9—C14	120.6 (2)	C20—C21—H21	120.5
C10—C9—C8	120.2 (2)	N1—C22—C21	122.7 (2)
C14—C9—C8	119.2 (2)	N1—C22—H22	118.6
C9—C10—C11	119.8 (2)	C21—C22—H22	118.6
C9—C10—H10	120.1

N2—Cu1—O1—C1	10.7 (2)	Cu1—O2—C8—C9	−179.27 (16)
N1—Cu1—O1—C1	−158.7 (2)	N2—N3—C8—O2	−2.2 (3)
N2—Cu1—O2—C8	−0.24 (15)	N2—N3—C8—C9	178.60 (19)
N1—Cu1—O2—C8	168.87 (15)	O2—C8—C9—C10	−20.0 (3)
O1—Cu1—N1—C22	−171.09 (18)	N3—C8—C9—C10	159.3 (2)
N2—Cu1—N1—C22	76.9 (4)	O2—C8—C9—C14	160.2 (2)
O2—Cu1—N1—C22	6.06 (19)	N3—C8—C9—C14	−20.5 (3)
O1—Cu1—N1—C18	5.5 (2)	C14—C9—C10—C11	1.6 (4)
N2—Cu1—N1—C18	−106.5 (4)	C8—C9—C10—C11	−178.2 (2)
O2—Cu1—N1—C18	−177.36 (19)	C15—O3—C11—C10	−27.1 (5)
O1—Cu1—N2—C7	−8.4 (2)	C15—O3—C11—C12	155.1 (3)
O2—Cu1—N2—C7	175.7 (2)	C9—C10—C11—O3	−178.7 (3)
N1—Cu1—N2—C7	103.5 (4)	C9—C10—C11—C12	−0.9 (4)
O1—Cu1—N2—N3	175.03 (16)	C16—O4—C12—C11	−76.1 (4)
O2—Cu1—N2—N3	−0.85 (15)	C16—O4—C12—C13	107.2 (3)
N1—Cu1—N2—N3	−73.0 (4)	O3—C11—C12—O4	1.2 (4)
C7—N2—N3—C8	−175.3 (2)	C10—C11—C12—O4	−176.8 (2)
Cu1—N2—N3—C8	1.7 (2)	O3—C11—C12—C13	177.8 (3)
Cu1—O1—C1—C6	172.93 (17)	C10—C11—C12—C13	−0.2 (4)
Cu1—O1—C1—C2	−9.2 (3)	C17—O5—C13—C12	−172.3 (3)
O1—C1—C2—C3	−177.2 (2)	C17—O5—C13—C14	8.6 (4)
C6—C1—C2—C3	0.7 (3)	O4—C12—C13—O5	−1.9 (4)
O1—C1—C2—C7	1.6 (4)	C11—C12—C13—O5	−178.6 (3)
C6—C1—C2—C7	179.5 (2)	O4—C12—C13—C14	177.3 (2)
C1—C2—C3—C4	0.1 (4)	C11—C12—C13—C14	0.6 (4)
C7—C2—C3—C4	−178.8 (2)	C10—C9—C14—C13	−1.2 (4)
C2—C3—C4—C5	−0.8 (4)	C8—C9—C14—C13	178.7 (2)
C2—C3—C4—Cl1	179.08 (18)	O5—C13—C14—C9	179.2 (3)
C3—C4—C5—C6	0.7 (4)	C12—C13—C14—C9	0.1 (4)
Cl1—C4—C5—C6	−179.1 (2)	C22—N1—C18—C19	1.0 (4)
C4—C5—C6—C1	0.1 (4)	Cu1—N1—C18—C19	−175.7 (2)
O1—C1—C6—C5	177.2 (2)	N1—C18—C19—C20	0.7 (4)
C2—C1—C6—C5	−0.8 (4)	C18—C19—C20—C21	−1.2 (4)
N3—N2—C7—C2	−179.1 (2)	C19—C20—C21—C22	0.3 (4)
Cu1—N2—C7—C2	4.4 (4)	C18—N1—C22—C21	−2.0 (4)
C3—C2—C7—N2	179.7 (2)	Cu1—N1—C22—C21	174.66 (19)
C1—C2—C7—N2	0.9 (4)	C20—C21—C22—N1	1.5 (4)
Cu1—O2—C8—N3	1.5 (3)

Experimental details

Crystal data
Chemical formula	[Cu(C₁₇H₁₅ClN₂O₅)(C₅H₅N)]
M_r	505.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	14.274 (4), 7.5763 (18), 20.753 (5)
β (°)	99.108 (4)
V (Å³)	2216.1 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.15
Crystal size (mm)	0.19 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.812, 0.875
No. of measured, independent and observed [I > 2σ(I)] reflections	11265, 3908, 3184
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.086, 1.04
No. of reflections	3908
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.37

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chan, S. C., Koh, L. L., Leung, P. H., Ranford, J. D. & Sim, K. Y. (1995). Inorg. Chim. Acta, 236, 101–108. CrossRef CAS Web of Science Google Scholar
Lee, P. F., Yang, C. T., Fan, D., Vittal, J. J. & Ranford, J. D. (2003). Polyhedron, 22, 2781–2786. CrossRef CAS Google Scholar
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