(4-Amino­benzoato-κ2O,O′)­chlorido(di-2-pyridylamine-κ2N,N′)­copper(II) monohydrate

Okabe, N.; Tsuji, A.; Yodoshi, M.

doi:10.1107/S1600536807032837

(4-Aminobenzoato-κ²O,O′)chlorido(di-2-pyridylamine-κ²N,N′)copper(II) monohydrate

In the title compound, [Cu(C₇H₆NO₂)Cl(C₁₀H₉N₃)]·H₂O, the Cu atom has a distorted square-pyramidal geometry defined by one N,N-bidentate 2,2′-bipyridylamine (C₁₀H₉N₃) molecule, one O,O-bidentate p-aminobenzenecarboxylate (C₇H₆NO₂⁻) anion and one apical chlorido ligand. The Cu atom deviates from the mean plane of the basal atoms towards the Cl atom by 0.2591 (1) Å. The component species are connected to each other by N—H

Cl, O—H

Cl, N—H

O and O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032837/hb2471sup1.cif Contains datablocks General, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032837/hb2471Isup2.hkl Contains datablock I

CCDC reference: 657558

checkCIF report

Key indicators

Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.002 Å
R factor = 0.021
wR factor = 0.062
Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT148_ALERT_3_B su on the      a  - Axis is Too Large (x 1000) .         10 Ang.
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Cu1    -   Cl1     ..      11.98 su

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.728     0.851
            Tmin and Tmax expected:      0.654     0.864
            RR =      1.130
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.13
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.02
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)       1000 Ang.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   O1      ..       6.18 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   O2      ..       5.04 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   C11     ..       7.03 su

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       2.30

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

As part of our studies of new therapeutic drugs, we have reported the structures of the ternary Cu(II) complexes with the heterocyclic ligand, 2,2'-bipyridylamine (bpa) and various carboxylate-containing compounds, such as bpa and p-hydroxybenzenecarboxylate (p-HB) (Wang & Okabe, 2005), cyclobutane-1,1-dicarboxylate (Yodoshi, Mototsuji & Okabe, 2007), benzenecarboxylate (BA) (Okabe et al., 2007), and glycine (Yodoshi, Odoko & Okabe, 2007). In this study, we report the structure of the title Cu(II) complex, (I), with bpa and the p-aminobenzenecarboxylate (p-ABA) and chloride anions. An uncoordinated water molecule completes the structure.

The overall structure of (I) is similar to those of the Cu(II) complexes with bpa and p-HB (Wang & Okabe, 2005) and BA (Okabe et al., 2007). The central Cu atom in (I) (Fig. 1) has a square pyramidal CuN₂O₂Cl geometry (Table 1), resulting from its coordination by two N atoms from one bpa and two O atoms from one p-ABA and one chloride anion. The four basal ligand atoms (N1, N2,O1 and O2) are neary coplanar, and the Cu atom deviates from the mean square plane towards the apical Cl atom by 0.2591 (1) Å. The bite angles N1—Cu1—N2 and O1—Cu1—O2 are in the range normally observed for these complexes (Wang & Okabe, 2005; Okabe et al., 2007; Yodoshi, Mototsuji & Okabe, 2007; Yodoshi, Odoko & Okabe, 2007; Youngme et al., 2004). The Cu—Cl distance of 2.597 (1)%A in (I) is slightly longer than the median of the known values from 2.336 (2) to 2.733 (2) Å (Mao et al., 2004; Brophy et al., 1999) Such long Cu—Cl bonds are explained by the well known Jahn-Teller effect.

As shown in Fig. 2, the crystal structure of (I) is stabilized by N—H···Cl, O—H···Cl, N—H···O, and O—H···O hydrogen bonds (Table 2), and no π-π stacking interactions are present.

Related literature top

For related literature, see: Brophy et al. (1999); Mao et al. (2004); Okabe et al. (2007); Wang & Okabe (2005); Yodoshi, Mototsuji & Okabe (2007); Yodoshi, Odoko & Okabe (2007); Youngme et al. (2004).

For related literature, see: Altomare et al. (1999); Farrugia (1997); Kelland (2005); Li et al. (2005); Ranford et al. (1993); Selvakumar et al. (2006); Spek (2003).

Experimental top

2,2'-Bipyridylamine (5.0 mg, 0.03 mol) dissolved in 90%(v/v) methanol-water solution (2 ml) was reacted with p-aminobenzoic acid (4.0 mg, 0.03 mol), dissolved in the same solution (2 ml) for 5 min at room temperature. This was followed by the addition of CuCl₂.2H₂O (5.0 mg, 0.03 mol) dissolved in H₂O (1 ml) and reacted for 15 min at room temperature. After several days green prismatic crystals of (I) appeared from the mother liquor.

Structure description top

For related literature, see: Altomare et al. (1999); Farrugia (1997); Kelland (2005); Li et al. (2005); Ranford et al. (1993); Selvakumar et al. (2006); Spek (2003).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2005) and CRYSTALS (Betteridge et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997), and PLATON (Spek, 2003); software used to prepare material for publication: CrystalStructure.

Figures top

	Fig. 1. View of the molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level (arbitrary spheres for the H atoms).
	Fig. 2. A view of the hydrogen bonds (dashed lines) in (I). Symmetry codes as in Table 2.

(4-Aminobenzoato-κ²O,O')chlorido(di-2-pyridylamine-\k²N,N')copper(II) monohydrat top

Crystal data top

[Cu(C₇H₆NO₂)Cl(C₁₀H₉N₃)]·H₂O	F(000) = 868.00
M_r = 424.35	D_x = 1.646 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yn	Cell parameters from 14678 reflections
a = 9.86 (1) Å	θ = 3.2–27.5°
b = 12.10 (1) Å	µ = 1.46 mm⁻¹
c = 14.60 (1) Å	T = 123 K
β = 100.63 (3)°	Prism, green
V = 1712 (3) Å³	0.30 × 0.30 × 0.10 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	3424 reflections with F² > 2.0σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.017
ω scans	θ_max = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
T_min = 0.728, T_max = 0.851	k = −14→15
16167 measured reflections	l = −18→18
3922 independent reflections

Refinement top

Refinement on F²	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.021	w = 1/[σ²(F_o²) + (0.036P)² + 0.6204P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.062	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.36 e Å⁻³
3922 reflections	Δρ_min = −0.42 e Å⁻³
242 parameters

Crystal data top

[Cu(C₇H₆NO₂)Cl(C₁₀H₉N₃)]·H₂O	V = 1712 (3) Å³
M_r = 424.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.86 (1) Å	µ = 1.46 mm⁻¹
b = 12.10 (1) Å	T = 123 K
c = 14.60 (1) Å	0.30 × 0.30 × 0.10 mm
β = 100.63 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3922 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3424 reflections with F² > 2.0σ(F²)
T_min = 0.728, T_max = 0.851	R_int = 0.017
16167 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	242 parameters
wR(F²) = 0.062	H-atom parameters constrained
S = 1.07	Δρ_max = 0.36 e Å⁻³
3922 reflections	Δρ_min = −0.42 e Å⁻³

Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
Cu1	0.93181 (2)	0.23066 (1)	0.48560 (1)	0.01293 (6)
Cl1	0.70895 (4)	0.33281 (3)	0.40723 (2)	0.01702 (8)
O1	0.9042 (1)	0.08460 (8)	0.40938 (7)	0.0156 (2)
O2	0.8285 (1)	0.11464 (8)	0.53813 (7)	0.0177 (2)
O3	0.5317 (1)	0.51357 (9)	0.26822 (8)	0.0225 (2)
N1	1.0627 (1)	0.3078 (1)	0.42339 (8)	0.0131 (2)
N2	0.9776 (1)	0.32012 (9)	0.60007 (8)	0.0137 (2)
N3	1.1401 (1)	0.43479 (9)	0.54583 (8)	0.0140 (2)
N4	0.4964 (1)	−0.3283 (1)	0.41741 (9)	0.0212 (3)
C1	1.0691 (1)	0.2727 (1)	0.3360 (1)	0.0160 (3)
C2	1.1551 (1)	0.3188 (1)	0.2827 (1)	0.0178 (3)
C3	1.2434 (1)	0.4038 (1)	0.3211 (1)	0.0185 (3)
C4	1.2391 (1)	0.4396 (1)	0.4095 (1)	0.0169 (3)
C5	1.1449 (1)	0.3914 (1)	0.45928 (9)	0.0129 (2)
C6	1.0676 (1)	0.4034 (1)	0.61365 (9)	0.0128 (2)
C7	1.0937 (1)	0.4632 (1)	0.69802 (9)	0.0162 (3)
C8	1.0244 (2)	0.4345 (1)	0.7678 (1)	0.0196 (3)
C9	0.9302 (2)	0.3477 (1)	0.7538 (1)	0.0221 (3)
C10	0.9100 (2)	0.2933 (1)	0.6701 (1)	0.0189 (3)
C11	0.8334 (1)	0.0513 (1)	0.46906 (9)	0.0137 (3)
C12	0.7553 (1)	−0.0525 (1)	0.45855 (9)	0.0131 (3)
C13	0.6597 (1)	−0.0730 (1)	0.51656 (9)	0.0159 (3)
C14	0.5743 (1)	−0.1639 (1)	0.50303 (9)	0.0170 (3)
C15	0.5830 (1)	−0.2395 (1)	0.4310 (1)	0.0151 (3)
C16	0.6805 (1)	−0.2201 (1)	0.37370 (9)	0.0141 (3)
C17	0.7645 (1)	−0.1280 (1)	0.38739 (9)	0.0138 (3)
H1	1.0125	0.2146	0.3110	0.019*
H2	1.1545	0.2941	0.2223	0.021*
H3	1.3044	0.4356	0.2871	0.022*
H4	1.2981	0.4954	0.4364	0.020*
H5	1.1568	0.5211	0.7062	0.019*
H6	1.0402	0.4728	0.8239	0.024*
H7	0.8822	0.3271	0.8002	0.027*
H8	0.8471	0.2353	0.6607	0.023*
H9	1.1917	0.4918	0.5601	0.017*
H10	0.6539	−0.0245	0.5650	0.019*
H11	0.5105	−0.1754	0.5417	0.020*
H12	0.6884	−0.2696	0.3263	0.017*
H13	0.8282	−0.1159	0.3487	0.017*
H14	0.5007	−0.3740	0.3729	0.025*
H15	0.4376	−0.3386	0.4533	0.025*
H16	0.5769	0.4615	0.2935	0.034*
H17	0.5563	0.5234	0.2197	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0154 (1)	0.0118 (1)	0.0125 (1)	−0.00460 (6)	0.00479 (6)	−0.00184 (5)
Cl1	0.0150 (2)	0.0150 (2)	0.0205 (2)	−0.0028 (1)	0.0018 (1)	0.0013 (1)
O1	0.0181 (5)	0.0133 (5)	0.0165 (5)	−0.0038 (4)	0.0061 (4)	−0.0009 (3)
O2	0.0236 (6)	0.0142 (5)	0.0165 (5)	−0.0071 (4)	0.0071 (4)	−0.0031 (4)
O3	0.0275 (6)	0.0224 (6)	0.0199 (6)	0.0061 (5)	0.0103 (4)	0.0033 (4)
N1	0.0128 (6)	0.0132 (6)	0.0135 (5)	−0.0009 (4)	0.0033 (4)	0.0000 (4)
N2	0.0147 (6)	0.0139 (6)	0.0126 (5)	−0.0023 (4)	0.0029 (4)	−0.0006 (4)
N3	0.0149 (6)	0.0122 (6)	0.0151 (6)	−0.0055 (4)	0.0034 (4)	−0.0019 (4)
N4	0.0250 (7)	0.0188 (6)	0.0210 (6)	−0.0108 (5)	0.0078 (5)	−0.0044 (5)
C1	0.0156 (7)	0.0163 (7)	0.0163 (7)	−0.0020 (5)	0.0032 (5)	−0.0028 (5)
C2	0.0184 (7)	0.0213 (7)	0.0150 (7)	−0.0001 (6)	0.0063 (5)	−0.0019 (5)
C3	0.0158 (7)	0.0218 (7)	0.0198 (7)	−0.0023 (6)	0.0079 (5)	0.0018 (5)
C4	0.0141 (7)	0.0171 (7)	0.0198 (7)	−0.0045 (5)	0.0039 (5)	−0.0001 (5)
C5	0.0121 (6)	0.0136 (6)	0.0131 (6)	0.0006 (5)	0.0022 (5)	0.0010 (5)
C6	0.0116 (6)	0.0126 (6)	0.0137 (6)	0.0010 (5)	0.0011 (5)	0.0006 (5)
C7	0.0150 (7)	0.0169 (7)	0.0163 (7)	−0.0038 (5)	0.0012 (5)	−0.0031 (5)
C8	0.0212 (8)	0.0243 (8)	0.0128 (7)	−0.0043 (6)	0.0021 (5)	−0.0049 (5)
C9	0.0258 (8)	0.0279 (8)	0.0141 (7)	−0.0094 (6)	0.0077 (6)	−0.0025 (6)
C10	0.0213 (8)	0.0198 (7)	0.0168 (7)	−0.0073 (6)	0.0066 (5)	−0.0022 (5)
C11	0.0132 (7)	0.0130 (6)	0.0142 (6)	0.0002 (5)	0.0008 (5)	0.0013 (5)
C12	0.0139 (7)	0.0111 (6)	0.0137 (6)	−0.0012 (5)	0.0008 (5)	0.0015 (4)
C13	0.0199 (7)	0.0149 (7)	0.0133 (6)	−0.0020 (5)	0.0041 (5)	−0.0012 (5)
C14	0.0192 (7)	0.0180 (7)	0.0150 (7)	−0.0041 (5)	0.0061 (5)	0.0001 (5)
C15	0.0159 (7)	0.0133 (6)	0.0149 (7)	−0.0019 (5)	−0.0003 (5)	0.0019 (5)
C16	0.0157 (7)	0.0133 (7)	0.0127 (6)	0.0005 (5)	0.0011 (5)	−0.0007 (4)
C17	0.0136 (7)	0.0144 (6)	0.0134 (6)	0.0020 (5)	0.0025 (5)	0.0027 (5)

Geometric parameters (Å, º) top

Cu1—Cl1	2.596 (3)	C3—C4	1.370 (2)
Cu1—O1	2.080 (1)	C3—H3	0.9300
Cu1—O2	1.972 (1)	C4—C5	1.408 (2)
Cu1—N1	1.948 (1)	C4—H4	0.9300
Cu1—N2	1.973 (1)	C6—C7	1.411 (2)
O1—C11	1.278 (2)	C7—C8	1.371 (2)
O2—C11	1.275 (2)	C7—H5	0.9299
O3—H16	0.8189	C8—C9	1.393 (2)
O3—H17	0.7997	C8—H6	0.9300
N1—C1	1.358 (2)	C9—C10	1.370 (2)
N1—C5	1.341 (2)	C9—H7	0.9299
N2—C6	1.334 (2)	C10—H8	0.9300
N2—C10	1.359 (2)	C11—C12	1.468 (2)
N3—C5	1.378 (2)	C12—C13	1.401 (2)
N3—C6	1.378 (2)	C12—C17	1.399 (2)
N3—H9	0.8601	C13—C14	1.378 (2)
N4—C15	1.364 (2)	C13—H10	0.9299
N4—H14	0.8600	C14—C15	1.408 (2)
N4—H15	0.8600	C14—H11	0.9299
C1—C2	1.371 (2)	C15—C16	1.406 (2)
C1—H1	0.9300	C16—C17	1.382 (2)
C2—C3	1.397 (2)	C16—H12	0.9299
C2—H2	0.9301	C17—H13	0.9300

O1—Cu1—O2	64.96 (4)	H4—C4—C3	120.1972
O1—Cu1—N1	100.99 (5)	C7—C6—N2	121.8 (1)
O1—Cu1—N2	155.07 (4)	C7—C6—N3	116.8 (1)
O2—Cu1—N1	163.19 (5)	C8—C7—C6	118.9 (1)
O2—Cu1—N2	96.61 (5)	C8—C7—H5	120.5419
N1—Cu1—N2	93.69 (5)	H5—C7—C6	120.5617
C11—O1—Cu1	86.39 (8)	C9—C8—C7	119.5 (1)
C11—O2—Cu1	91.27 (9)	C9—C8—H6	120.2575
H16—O3—H17	106.5428	H6—C8—C7	120.2656
C1—N1—Cu1	116.01 (9)	C10—C9—C8	118.5 (2)
C1—N1—C5	118.2 (1)	C10—C9—H7	120.7387
C5—N1—Cu1	125.8 (1)	H7—C9—C8	120.7571
C6—N2—Cu1	125.6 (1)	H8—C10—N2	118.4789
C6—N2—C10	118.3 (1)	H8—C10—C9	118.4777
C10—N2—Cu1	116.05 (9)	C12—C11—O1	122.7 (1)
C5—N3—C6	131.6 (1)	C12—C11—O2	120.1 (1)
C5—N3—H9	114.1757	C13—C12—C11	119.2 (1)
C6—N3—H9	114.1759	C13—C12—C17	118.5 (1)
C15—N4—H14	120.0009	C17—C12—C11	122.1 (1)
C15—N4—H15	119.9993	C14—C13—C12	121.1 (1)
H14—N4—H15	119.9998	C14—C13—H10	119.4483
C2—C1—N1	123.2 (1)	H10—C13—C12	119.4502
C2—C1—H1	118.3955	C15—C14—C13	120.4 (1)
H1—C1—N1	118.3871	C15—C14—H11	119.8033
C3—C2—C1	118.5 (1)	H11—C14—C13	119.8016
C3—C2—H2	120.7520	C16—C15—N4	121.5 (1)
H2—C2—C1	120.7608	C16—C15—C14	118.6 (1)
C4—C3—C2	119.1 (1)	C17—C16—C15	120.4 (1)
C4—C3—H3	120.4688	C17—C16—H12	119.7788
H3—C3—C2	120.4693	H12—C16—C15	119.7821
C5—C4—C3	119.6 (1)	H13—C17—C12	119.5207
C5—C4—H4	120.2014	H13—C17—C16	119.5239

O2—Cu1—O1—C11	3.07 (6)	C1—C2—C3—C4	−1.4 (2)
O1—Cu1—O2—C11	−3.07 (7)	C2—C3—C4—C5	−0.8 (2)
O1—Cu1—N1—C1	20.2 (1)	C3—C4—C5—N1	2.7 (2)
O1—Cu1—N2—C6	128.1 (1)	C3—C4—C5—N3	−176.6 (1)
Cu1—O1—C11—O2	−4.8 (1)	N2—C6—C7—C8	0.1 (2)
Cu1—O2—C11—O1	5.1 (1)	C6—C7—C8—C9	−0.1 (2)
Cu1—N1—C1—C2	179.5 (1)	C7—C8—C9—C10	0.1 (2)
Cu1—N1—C5—N3	−2.7 (2)	C8—C9—C10—N2	−0.0 (2)
Cu1—N1—C5—C4	178.1 (1)	O1—C11—C12—C13	−167.7 (1)
Cu1—N2—C6—N3	−0.4 (2)	C11—C12—C13—C14	173.4 (1)
Cu1—N2—C10—C9	−179.9 (1)	C11—C12—C17—C16	−173.9 (1)
C6—N3—C5—N1	5.3 (2)	C12—C13—C14—C15	1.0 (2)
C6—N3—C5—C4	−175.5 (1)	C13—C14—C15—N4	−179.0 (1)
C5—N3—C6—N2	−3.6 (2)	N4—C15—C16—C17	178.3 (1)
H14—N4—C15—C14	179.0	C15—C16—C17—C12	0.4 (2)
N1—C1—C2—C3	2.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H9···Cl1ⁱ	0.86	2.35	3.196 (3)	169
N4—H14···O3ⁱⁱ	0.86	2.11	2.968 (2)	174
N4—H15···Cl1ⁱⁱⁱ	0.86	2.71	3.547 (2)	166
O3—H16···Cl1	0.82	2.47	3.263 (4)	164
O3—H17···O1^iv	0.80	2.13	2.911 (2)	166

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

Experimental details

Crystal data
Chemical formula	[Cu(C₇H₆NO₂)Cl(C₁₀H₉N₃)]·H₂O
M_r	424.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	123
a, b, c (Å)	9.86 (1), 12.10 (1), 14.60 (1)
β (°)	100.63 (3)
V (Å³)	1712 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.46
Crystal size (mm)	0.30 × 0.30 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.728, 0.851
No. of measured, independent and observed [F² > 2.0σ(F²)] reflections	16167, 3922, 3424
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.062, 1.07
No. of reflections	3922
No. of parameters	242
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.42

Computer programs: RAPID-AUTO (Rigaku, 1998), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2005) and CRYSTALS (Betteridge et al., 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), and PLATON (Spek, 2003), CrystalStructure.

Selected geometric parameters (Å, º) top

Cu1—Cl1	2.596 (3)	Cu1—N1	1.948 (1)
Cu1—O1	2.080 (1)	Cu1—N2	1.973 (1)
Cu1—O2	1.972 (1)

O1—Cu1—O2	64.96 (4)	N1—Cu1—N2	93.69 (5)