(2-{[2-Carboxyl­ato-1-(4-chloro­phen­yl)eth­yl]imino­meth­yl}phenolato-κ3O,N,O′)(1H-imidazole-κN3)copper(II) monohydrate

Zhou, W.-J.; Jiang, Y.-Z.; Zou, Y.

doi:10.1107/S1600536810014765

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages m579-m580

https://doi.org/10.1107/S1600536810014765

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(2-{[2-Carboxylato-1-(4-chlorophenyl)ethyl]iminomethyl}phenolato-κ³O,N,O′)(1H-imidazole-κN³)copper(II) monohydrate

Wen-Jun Zhou,^a Yin-Zhi Jiang ^a and Yang Zou ^a ^*

^aChemistry Department, Zhejiang Sci-Tech University, Hangzhou 310018, People's Republic of China
^*Correspondence e-mail: zouyang@zstu.edu.cn

(Received 12 April 2010; accepted 22 April 2010; online 28 April 2010)

The Cu^II atom of the title complex, [Cu(C₁₆H₁₂ClNO₃)(C₃H₄N₂)]·H₂O, has a distorted square-planar coordination geometry formed by a tridentate Schiff base dianion and an imidazole ligand. The imidazole is nearly coplanar with the coordination plane, the dihedral angle between the planes being 3.73 (12)°. In the Schiff base ligand, the two benzene rings are oriented at a dihedral angle of 75.87 (12)°. O—H⋯O and N—H⋯O hydrogen bonding is present in the crystal structure. One H atom of the uncoordinated water molecule is disordered equally over two sites.

Related literature

Transition metal complexes of salicylaldehyde-peptides and salicylaldehyde-aminoacid Schiff bases are non-enzymatic models for pyridoxal amino acid systems, which are of importance as key intermediates in many metabolic reactions of amino acid catalyses by enzymes, see: Bkouche-Waksman et al. (1988 ); Wetmore et al. (2001 ); Zabinski & Toney (2001 ). For the preparation, structural characterization, appropriate spectroscopy and magnetic studies of Schiff-base complexes derived from salicylaldehyde and amino acids, see: Ganguly et al. (2008 ) and references cited therein. For Schiff bases derived from β-amino acids, see: Vančo et al. (2008 ).

Experimental

Crystal data

[Cu(C₁₆H₁₂ClNO₃)(C₃H₄N₂)]·H₂O
M_r = 451.35
Monoclinic, C 2/c
a = 23.884 (1) Å
b = 4.944 (1) Å
c = 32.008 (1) Å
β = 96.88 (1)°
V = 3752.4 (8) Å³
Z = 8
Mo Kα radiation
μ = 1.34 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.776, T_max = 0.825
18085 measured reflections
4310 independent reflections
3298 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.087
S = 1.04
4310 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.8894 (16)
Cu1—O3	1.9494 (16)
Cu1—N1	1.9582 (18)
Cu1—N2	1.9789 (18)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O2ⁱ	0.87	1.98	2.799 (3)	156
O1W—H2W1⋯O1Wⁱⁱ	0.82	2.01	2.826 (4)	172
O1W—H2W2⋯O1Wⁱⁱⁱ	0.83	2.02	2.822 (5)	163
N3—H3A⋯O2^iv	0.86	1.90	2.758 (3)	172
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) -x+1, -y+2, -z; (iii) -x+1, -y+1, -z; (iv) $[-x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810014765/xu2751sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810014765/xu2751Isup2.hkl

checkCIF report

Comment top

Transition metal complexes of salicylaldehyde-peptides and salicylaldehyde-amino acid Schiff base are non-enzymatic models for pyridoxal-amino acid systems, which are of considerable importance as key intermediates in many metabolic reactions of amino acids catalyzed by enzymes (Zabinski et al., 2001; Wetmore et al., 2001; Bkouche-Waksman et al.,1988). Considerable effort has been devoted to the preparation, structural characterization, appropriate spectroscopy and magnetic studies of Schiff-base complexes derived from salicylaldehyde and amino acids and reduced salicylidene amino acid (Ganguly et al., 2008), but little attention has been given to Schiff base derived from β-amino acid (Vančo et al., 2008). Herein, we report the structure study of [Cu(L)(C₃H₄N₂)]^.H₂O (H₂L= Schiff bases derived from glycylglycine and salicylaldehyde, C₁₆H₁₄NO₃Cl).

The complex crystallizes in the monoclinic space group C2/c. The title molecule,is characterized by a square-planar Cu^II coordination with the deprotonated tridentate Schiff base dianion and one imidazole molecule in the basal plane (Fig. 1). The Cu1—N1 bond distance is 1.958 Å. The two Cu—O bonds are 1.889(Cu1—O1) and 1.950 Å (Cu1—O3). The fourth position occupied by one N atom from the imidazole ligand, with bond length of 1.980 Å (Cu1—N2). The phenyl ring [C1—C6] and the ring of C1, C6, C7, N1, O1, Cu1 chelate ring are almost coplanar with a small dihedral angle of 1.8^o. Hydrogen bond between the coordinated imidazole molecule and the carboxyl oxygen atom of an adjacent, symmetry related CuL unit leads to the formation of a [CuL(C₃H₄N₂)]₂ dimer. Hydrogen bond between water molecule and CuL unit further link the dimers into two-dimension layers (Fig. 2).

Related literature top

Transition metal complexes of salicylaldehyde-peptides and salicylaldehyde-aminoacid Schiff bases are non-enzymatic models for pyridoxal amino acid systems, which are of importance as key intermediates in many metabolic reactions of amino acid catalyses by enzymes, see: Bkouche-Waksman et al. (1988); Wetmore et al. (2001); Zabinski & Toney (2001). For the preparation, structural characterization, appropriate spectroscopy and magnetic studies of Schiff-base complexes derived from salicylaldehyde and amino acids, see: Ganguly et al. (2008) and references cited therein. For Schiff bases derived from β-amino acid, see: Vančo et al. (2008).

Experimental top

The Schiff base was prepared through the condensation of 3-amino-3-(4-chlorophenyl) propionic acid and salicylaldehyde. 3-Amino-3-(4-chlorophenyl) propionic acid (10 mmol) was dissolved and refluxed in absolute methanol (40 ml) containing LiOH^.H₂O (10 mmol). After cooled to room temperature, a solution of salicylaldehyde (10 mmol) in absolute methanol was added slowly with stirring over 10 min. Then Cu(NO₃)₂ (10 mmol) was added to the HLLi solution and the resulting solution was adjusted to the pH = 9-11 by 1.0 mol/L NaOH solution. After stirring at room temperature for 30 min, imidazole (10 mmol) was added to the solution with stirring. The resulting clear solution was then filtered. The filtrate was allowed to evaporate slowly at room temperature. After several days dark green crystals suitable for X-ray diffraction were obtained.

Structure description top

Transition metal complexes of salicylaldehyde-peptides and salicylaldehyde-aminoacid Schiff bases are non-enzymatic models for pyridoxal amino acid systems, which are of importance as key intermediates in many metabolic reactions of amino acid catalyses by enzymes, see: Bkouche-Waksman et al. (1988); Wetmore et al. (2001); Zabinski & Toney (2001). For the preparation, structural characterization, appropriate spectroscopy and magnetic studies of Schiff-base complexes derived from salicylaldehyde and amino acids, see: Ganguly et al. (2008) and references cited therein. For Schiff bases derived from β-amino acid, see: Vančo et al. (2008).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title complex with atom numbering scheme; thermal ellipsoids are drawn at 40% probability level.
	Fig. 2. Schematic representation of the hydrogen-bonded (dashed lines).

(2-{[2-Carboxylato-1-(4-chlorophenyl)ethyl]iminomethyl}phenolato- κ³O,N,O')(1H-imidazole-κN³)copper(II) monohydrate top

Crystal data top

[Cu(C₁₆H₁₂ClNO₃)(C₃H₄N₂)]·H₂O	F(000) = 1848
M_r = 451.35	D_x = 1.598 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3298 reflections
a = 23.884 (1) Å	θ = 1.7–27.5°
b = 4.944 (1) Å	µ = 1.34 mm⁻¹
c = 32.008 (1) Å	T = 296 K
β = 96.88 (1)°	Block, dark green
V = 3752.4 (8) Å³	0.20 × 0.20 × 0.15 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	4310 independent reflections
Radiation source: fine-focus sealed tube	3298 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
φ and ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −30→30
T_min = 0.776, T_max = 0.825	k = −6→6
18085 measured reflections	l = −41→41

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0381P)² + 2.3614P] where P = (F_o² + 2F_c²)/3
4310 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Cu(C₁₆H₁₂ClNO₃)(C₃H₄N₂)]·H₂O	V = 3752.4 (8) Å³
M_r = 451.35	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.884 (1) Å	µ = 1.34 mm⁻¹
b = 4.944 (1) Å	T = 296 K
c = 32.008 (1) Å	0.20 × 0.20 × 0.15 mm
β = 96.88 (1)°

Data collection top

Bruker SMART CCD diffractometer	4310 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	3298 reflections with I > 2σ(I)
T_min = 0.776, T_max = 0.825	R_int = 0.035
18085 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.04	Δρ_max = 0.33 e Å⁻³
4310 reflections	Δρ_min = −0.30 e Å⁻³
253 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.257392 (11)	0.70003 (6)	0.103939 (8)	0.03102 (10)
Cl1	−0.00394 (3)	1.30201 (17)	0.18252 (3)	0.0645 (2)
N1	0.20142 (7)	0.4707 (4)	0.12667 (6)	0.0301 (4)
N2	0.31243 (7)	0.9444 (4)	0.08174 (6)	0.0332 (4)
N3	0.34883 (9)	1.2624 (4)	0.04560 (7)	0.0414 (5)
H3A	0.3513	1.3915	0.0279	0.050*
O1	0.31821 (6)	0.5542 (4)	0.14014 (5)	0.0406 (4)
O2	0.13208 (7)	0.8259 (4)	0.00906 (5)	0.0425 (4)
O3	0.20152 (7)	0.8490 (4)	0.06065 (5)	0.0436 (4)
C1	0.31811 (10)	0.3666 (5)	0.16842 (7)	0.0351 (5)
C2	0.36998 (10)	0.2833 (6)	0.19110 (8)	0.0439 (6)
H2	0.4033	0.3671	0.1858	0.053*
C3	0.37183 (11)	0.0827 (6)	0.22041 (7)	0.0447 (6)
H3	0.4065	0.0316	0.2346	0.054*
C4	0.32307 (11)	−0.0477 (6)	0.22958 (8)	0.0462 (7)
H4	0.3250	−0.1838	0.2498	0.055*
C5	0.27261 (10)	0.0272 (5)	0.20854 (7)	0.0409 (6)
H5	0.2400	−0.0594	0.2146	0.049*
C6	0.26851 (10)	0.2331 (5)	0.17774 (7)	0.0329 (5)
C7	0.21439 (10)	0.2914 (5)	0.15579 (7)	0.0335 (5)
H7	0.1846	0.1879	0.1633	0.040*
C8	0.14124 (9)	0.4717 (5)	0.10794 (7)	0.0308 (5)
H8	0.1251	0.2993	0.1157	0.037*
C9	0.10709 (9)	0.6933 (5)	0.12577 (7)	0.0313 (5)
C10	0.11509 (10)	0.7554 (5)	0.16848 (8)	0.0383 (6)
H10	0.1440	0.6701	0.1857	0.046*
C11	0.08136 (10)	0.9405 (6)	0.18610 (8)	0.0433 (6)
H11	0.0875	0.9788	0.2147	0.052*
C12	0.03856 (10)	1.0673 (5)	0.16069 (8)	0.0426 (6)
C13	0.02920 (10)	1.0118 (5)	0.11820 (8)	0.0431 (6)
H13	0.0003	1.0987	0.1013	0.052*
C14	0.06307 (9)	0.8260 (5)	0.10105 (8)	0.0387 (6)
H14	0.0565	0.7881	0.0724	0.046*
C15	0.13857 (9)	0.4720 (5)	0.05973 (7)	0.0331 (5)
H15A	0.1617	0.3250	0.0513	0.040*
H15B	0.1000	0.4373	0.0477	0.040*
C16	0.15803 (9)	0.7320 (5)	0.04156 (7)	0.0325 (5)
C17	0.30207 (10)	1.1329 (5)	0.05273 (7)	0.0385 (6)
H17	0.2664	1.1707	0.0389	0.046*
C18	0.39202 (11)	1.1523 (6)	0.07154 (8)	0.0487 (7)
H18	0.4298	1.2016	0.0735	0.058*
C19	0.36968 (9)	0.9583 (6)	0.09385 (8)	0.0408 (6)
H19	0.3897	0.8504	0.1142	0.049*
O1W	0.48323 (8)	0.7498 (5)	0.01584 (7)	0.0703 (6)
H1W	0.4469	0.7337	0.0159	0.084*
H2W1	0.4959	0.8883	0.0066	0.084*	0.50
H2W2	0.4987	0.6209	0.0050	0.084*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02878 (15)	0.03081 (17)	0.03347 (16)	−0.00405 (12)	0.00374 (11)	0.00462 (13)
Cl1	0.0498 (4)	0.0640 (5)	0.0836 (6)	0.0023 (4)	0.0240 (4)	−0.0184 (4)
N1	0.0281 (9)	0.0298 (11)	0.0323 (10)	−0.0028 (8)	0.0034 (8)	0.0038 (9)
N2	0.0315 (10)	0.0363 (12)	0.0314 (10)	−0.0053 (9)	0.0027 (8)	0.0040 (9)
N3	0.0459 (12)	0.0394 (13)	0.0399 (11)	−0.0119 (10)	0.0094 (9)	0.0071 (10)
O1	0.0320 (8)	0.0453 (11)	0.0439 (10)	−0.0041 (8)	0.0017 (7)	0.0127 (9)
O2	0.0417 (9)	0.0455 (11)	0.0387 (9)	−0.0073 (8)	−0.0022 (8)	0.0123 (8)
O3	0.0362 (9)	0.0392 (11)	0.0525 (10)	−0.0121 (8)	−0.0064 (8)	0.0160 (9)
C1	0.0399 (13)	0.0362 (14)	0.0290 (12)	0.0020 (11)	0.0040 (10)	−0.0005 (11)
C2	0.0349 (13)	0.0546 (18)	0.0418 (14)	0.0031 (12)	0.0025 (11)	0.0028 (13)
C3	0.0447 (14)	0.0524 (17)	0.0354 (13)	0.0139 (13)	−0.0020 (11)	0.0034 (13)
C4	0.0584 (16)	0.0458 (17)	0.0340 (13)	0.0074 (14)	0.0034 (12)	0.0102 (12)
C5	0.0450 (14)	0.0396 (15)	0.0381 (13)	−0.0007 (12)	0.0050 (11)	0.0069 (12)
C6	0.0354 (12)	0.0322 (13)	0.0310 (12)	0.0030 (10)	0.0044 (9)	0.0014 (10)
C7	0.0341 (12)	0.0310 (13)	0.0364 (12)	−0.0047 (11)	0.0081 (10)	0.0022 (11)
C8	0.0276 (11)	0.0297 (12)	0.0349 (12)	−0.0080 (10)	0.0026 (9)	0.0058 (10)
C9	0.0271 (11)	0.0332 (13)	0.0340 (12)	−0.0093 (10)	0.0043 (9)	0.0028 (11)
C10	0.0343 (12)	0.0436 (16)	0.0366 (13)	−0.0048 (11)	0.0023 (10)	0.0048 (11)
C11	0.0448 (14)	0.0499 (17)	0.0359 (13)	−0.0082 (13)	0.0076 (11)	−0.0029 (13)
C12	0.0344 (12)	0.0404 (15)	0.0552 (16)	−0.0069 (12)	0.0152 (11)	−0.0048 (13)
C13	0.0293 (12)	0.0477 (16)	0.0508 (15)	−0.0029 (12)	−0.0009 (11)	0.0003 (13)
C14	0.0329 (12)	0.0457 (16)	0.0367 (13)	−0.0029 (12)	0.0003 (10)	−0.0016 (12)
C15	0.0348 (12)	0.0282 (13)	0.0355 (12)	−0.0060 (10)	0.0009 (10)	−0.0003 (11)
C16	0.0325 (11)	0.0325 (13)	0.0332 (12)	−0.0026 (10)	0.0073 (10)	0.0018 (10)
C17	0.0354 (12)	0.0422 (15)	0.0381 (13)	−0.0083 (11)	0.0046 (10)	0.0050 (12)
C18	0.0370 (13)	0.0574 (19)	0.0522 (16)	−0.0136 (13)	0.0069 (12)	0.0030 (14)
C19	0.0319 (12)	0.0470 (16)	0.0425 (14)	−0.0066 (11)	0.0004 (10)	0.0069 (12)
O1W	0.0450 (11)	0.0803 (16)	0.0830 (15)	−0.0032 (11)	−0.0032 (11)	0.0025 (12)

Geometric parameters (Å, º) top

Cu1—O1	1.8894 (16)	C6—C7	1.425 (3)
Cu1—O3	1.9494 (16)	C7—H7	0.9300
Cu1—N1	1.9582 (18)	C8—C9	1.518 (3)
Cu1—N2	1.9789 (18)	C8—C15	1.537 (3)
Cl1—C12	1.742 (3)	C8—H8	0.9800
N1—C7	1.297 (3)	C9—C10	1.392 (3)
N1—C8	1.489 (3)	C9—C14	1.401 (3)
N2—C17	1.318 (3)	C10—C11	1.383 (3)
N2—C19	1.378 (3)	C10—H10	0.9300
N3—C17	1.331 (3)	C11—C12	1.379 (3)
N3—C18	1.358 (3)	C11—H11	0.9300
N3—H3A	0.8600	C12—C13	1.379 (3)
O1—C1	1.296 (3)	C13—C14	1.381 (3)
O2—C16	1.236 (3)	C13—H13	0.9300
O3—C16	1.278 (3)	C14—H14	0.9300
C1—C6	1.419 (3)	C15—C16	1.507 (3)
C1—C2	1.420 (3)	C15—H15A	0.9700
C2—C3	1.362 (4)	C15—H15B	0.9700
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.393 (4)	C18—C19	1.344 (3)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.360 (3)	C19—H19	0.9300
C4—H4	0.9300	O1W—H1W	0.8709
C5—C6	1.412 (3)	O1W—H2W1	0.8180
C5—H5	0.9300	O1W—H2W2	0.8325

O1—Cu1—O3	172.18 (7)	C9—C8—H8	106.6
O1—Cu1—N1	93.45 (7)	C15—C8—H8	106.6
O3—Cu1—N1	92.47 (7)	C10—C9—C14	117.2 (2)
O1—Cu1—N2	87.61 (7)	C10—C9—C8	120.8 (2)
O3—Cu1—N2	86.66 (7)	C14—C9—C8	121.8 (2)
N1—Cu1—N2	177.75 (8)	C11—C10—C9	121.9 (2)
C7—N1—C8	115.30 (18)	C11—C10—H10	119.1
C7—N1—Cu1	123.22 (15)	C9—C10—H10	119.1
C8—N1—Cu1	121.16 (14)	C12—C11—C10	119.2 (2)
C17—N2—C19	105.0 (2)	C12—C11—H11	120.4
C17—N2—Cu1	127.44 (16)	C10—C11—H11	120.4
C19—N2—Cu1	127.53 (16)	C11—C12—C13	120.8 (2)
C17—N3—C18	107.1 (2)	C11—C12—Cl1	119.5 (2)
C17—N3—H3A	126.5	C13—C12—Cl1	119.6 (2)
C18—N3—H3A	126.5	C12—C13—C14	119.4 (2)
C1—O1—Cu1	129.47 (15)	C12—C13—H13	120.3
C16—O3—Cu1	128.07 (16)	C14—C13—H13	120.3
O1—C1—C6	123.5 (2)	C13—C14—C9	121.5 (2)
O1—C1—C2	119.3 (2)	C13—C14—H14	119.2
C6—C1—C2	117.2 (2)	C9—C14—H14	119.2
C3—C2—C1	121.2 (2)	C16—C15—C8	114.26 (19)
C3—C2—H2	119.4	C16—C15—H15A	108.7
C1—C2—H2	119.4	C8—C15—H15A	108.7
C2—C3—C4	121.5 (2)	C16—C15—H15B	108.7
C2—C3—H3	119.2	C8—C15—H15B	108.7
C4—C3—H3	119.2	H15A—C15—H15B	107.6
C5—C4—C3	118.9 (2)	O2—C16—O3	122.0 (2)
C5—C4—H4	120.5	O2—C16—C15	119.9 (2)
C3—C4—H4	120.5	O3—C16—C15	118.1 (2)
C4—C5—C6	121.7 (2)	N2—C17—N3	111.7 (2)
C4—C5—H5	119.2	N2—C17—H17	124.1
C6—C5—H5	119.2	N3—C17—H17	124.1
C5—C6—C1	119.5 (2)	C19—C18—N3	106.9 (2)
C5—C6—C7	118.2 (2)	C19—C18—H18	126.6
C1—C6—C7	122.2 (2)	N3—C18—H18	126.6
N1—C7—C6	128.1 (2)	C18—C19—N2	109.3 (2)
N1—C7—H7	115.9	C18—C19—H19	125.4
C6—C7—H7	115.9	N2—C19—H19	125.4
N1—C8—C9	112.78 (18)	H1W—O1W—H2W1	119.3
N1—C8—C15	109.03 (17)	H1W—O1W—H2W2	115.1
C9—C8—C15	114.66 (19)	H2W1—O1W—H2W2	106.8
N1—C8—H8	106.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2ⁱ	0.87	1.98	2.799 (3)	156
O1W—H2W1···O1Wⁱⁱ	0.82	2.01	2.826 (4)	172
O1W—H2W2···O1Wⁱⁱⁱ	0.83	2.02	2.822 (5)	163
N3—H3A···O2^iv	0.86	1.90	2.758 (3)	172

Symmetry codes: (i) −x+1/2, −y+3/2, −z; (ii) −x+1, −y+2, −z; (iii) −x+1, −y+1, −z; (iv) −x+1/2, −y+5/2, −z.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₆H₁₂ClNO₃)(C₃H₄N₂)]·H₂O
M_r	451.35
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	23.884 (1), 4.944 (1), 32.008 (1)
β (°)	96.88 (1)
V (Å³)	3752.4 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.34
Crystal size (mm)	0.20 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.776, 0.825
No. of measured, independent and observed [I > 2σ(I)] reflections	18085, 4310, 3298
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.087, 1.04
No. of reflections	4310
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.30

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—O1	1.8894 (16)	Cu1—N1	1.9582 (18)
Cu1—O3	1.9494 (16)	Cu1—N2	1.9789 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2ⁱ	0.87	1.98	2.799 (3)	155.8
O1W—H2W1···O1Wⁱⁱ	0.82	2.01	2.826 (4)	172.3
O1W—H2W2···O1Wⁱⁱⁱ	0.83	2.02	2.822 (5)	163.2
N3—H3A···O2^iv	0.86	1.90	2.758 (3)	171.8

Symmetry codes: (i) −x+1/2, −y+3/2, −z; (ii) −x+1, −y+2, −z; (iii) −x+1, −y+1, −z; (iv) −x+1/2, −y+5/2, −z.

Acknowledgements

The authors thank the Natural Science Foundation of Zhejiang Province, China (No. Y4080342) and the Science Foundation of Zhejiang Sci-Tech University (No. 0813622-Y) for financial support.

References

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