Di-μ-chlorido-bis­[(2-anilinobenzoato-κ2O,O′)(1,10-phenanthroline-κ2N,N′)copper(II)]

Jiang, H.; Ma, J.-F.; Zhang, W.-L.

doi:10.1107/S1600536807024725

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Di-μ-chlorido-bis[(2-anilinobenzoato-κ²O,O′)(1,10-phenanthroline-κ²N,N′)copper(II)]

H. Jiang, J.-F. Ma and W.-L. Zhang

In the title compound, [Cu₂(C₁₃H₁₀NO₂)₂Cl₂(C₁₂H₈N₂)₂], the coordination geometry around the Cu^II atom is square-pyramidal, comprising one O atom from a 2-anilinobenzoate ligand, two N atoms from a 1,10-phenanthroline ligand and two Cl⁻ anions. In addition, there is a weak interaction of 2.700 (2) Å between the Cu^II atom and the other O atom of the 2-anilinobenzoate ligand. The two Cl⁻ anions bridge two Cu^II atoms to form a dimeric complex molecule, which lies on an inversion centre. There is an intramolecular N—H

O hydrogen bond in the 2-anilinobenzoate ligand.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024725/hy2064sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024725/hy2064Isup2.hkl Contains datablock I

CCDC reference: 650683

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.040
wR factor = 0.092
Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Cu1    -   Cl1_a   ..      12.21 su

Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       2.10

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

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

Comment top

As part of our investigation of the transition metal complexes, there is a need to prepare further examples of these compounds. In this paper, the structure of the title compound, (I), is described.

As shown in Fig. 1, the coordination polyhedron around the Cu^II atom is a square pyramid, comprising one O atom from a 2-anilinobenzoate ligand, two N atoms from a 1,10-phenanthroline ligand and two Cl^- anions. In addition, there is a weak interaction of 2.700 (2)Å between Cu1 and O2 (Table 1). The two Cl^- anions bridge two Cu^II atoms to form a dimeric complex molecule, which lies on an inversion center. The bond distances and angles are normal (Atria et al., 1994). There exists intramolecular N—H···O hydrogen bond in (I) (Table 2).

Related literature top

For a related structure, see: Atria et al. (1994).

Experimental top

A mixture of CuCl₂.2H₂O (0.171 g, 1 mmol), NaOH (0.08 g, 2 mmol) and 2-anilinobenzoic acid (0.426 g, 2 mmol) in ethanol (15 ml) was stirred for 10 min at room temperature. Then 1,10-phenanthroline (0.360 g, 1 mmol) was added to the solution with stirring for 30 min and a blue precipitate was obtained. The precipitate was dissolved by dropwise addition of ammonia (5 M). Green single crystals were obtained by slow evaporation of the solution at room temperature.

Structure description top

As part of our investigation of the transition metal complexes, there is a need to prepare further examples of these compounds. In this paper, the structure of the title compound, (I), is described.

For a related structure, see: Atria et al. (1994).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level. The dashed lines denote the weak interactions between Cu1 and O2. [Symmetry code: (i) -x + 1, -y + 1, -z + 1.]

Di-µ-chlorido-bis[(2-anilinobenzoato-κ²O,O')(1,10-phenanthroline- κ²N,N')copper(II)] top

Crystal data top

[Cu₂(C₁₃H₁₀NO₂)₂Cl₂(C₁₂H₈N₂)₂]	F(000) = 1004
M_r = 982.83	D_x = 1.511 Mg m⁻³
Monoclinic, P2₁/c	Melting point: not measured K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.1685 (18) Å	Cell parameters from 5099 reflections
b = 10.3545 (13) Å	θ = 2.4–28.3°
c = 14.9955 (19) Å	µ = 1.16 mm⁻¹
β = 100.843 (2)°	T = 293 K
V = 2160.7 (5) Å³	Block, green
Z = 2	0.40 × 0.32 × 0.28 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5099 independent reflections
Radiation source: fine-focus sealed tube	3284 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 28.3°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→17
T_min = 0.643, T_max = 0.718	k = −6→13
12962 measured reflections	l = −19→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0355P)²] where P = (F_o² + 2F_c²)/3
5099 reflections	(Δ/σ)_max = 0.001
292 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Cu₂(C₁₃H₁₀NO₂)₂Cl₂(C₁₂H₈N₂)₂]	V = 2160.7 (5) Å³
M_r = 982.83	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.1685 (18) Å	µ = 1.16 mm⁻¹
b = 10.3545 (13) Å	T = 293 K
c = 14.9955 (19) Å	0.40 × 0.32 × 0.28 mm
β = 100.843 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5099 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3284 reflections with I > 2σ(I)
T_min = 0.643, T_max = 0.718	R_int = 0.041
12962 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.30 e Å⁻³
5099 reflections	Δρ_min = −0.46 e Å⁻³
292 parameters

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

	x	y	z	U_iso*/U_eq
Cu1	0.38851 (2)	0.57806 (3)	0.46359 (2)	0.03554 (11)
C1	0.2915 (2)	0.7342 (3)	0.2981 (2)	0.0569 (8)
H1	0.2811	0.6567	0.2665	0.068*
C2	0.2601 (2)	0.8483 (4)	0.2536 (2)	0.0775 (11)
H2	0.2298	0.8463	0.1929	0.093*
C3	0.2735 (2)	0.9628 (4)	0.2984 (3)	0.0759 (10)
H3	0.2520	1.0391	0.2686	0.091*
C4	0.3194 (2)	0.9658 (3)	0.3892 (2)	0.0517 (7)
C5	0.34946 (17)	0.8467 (2)	0.42921 (18)	0.0380 (6)
C6	0.3382 (2)	1.0797 (3)	0.4440 (3)	0.0643 (9)
H6	0.3188	1.1596	0.4186	0.077*
C7	0.3832 (2)	1.0736 (3)	0.5312 (3)	0.0610 (9)
H7	0.3949	1.1495	0.5646	0.073*
C8	0.41356 (19)	0.9538 (2)	0.5737 (2)	0.0463 (7)
C9	0.39598 (17)	0.8408 (2)	0.52190 (17)	0.0361 (6)
C10	0.4697 (2)	0.7138 (3)	0.64042 (18)	0.0504 (7)
H10	0.4905	0.6333	0.6635	0.060*
C11	0.4894 (2)	0.8213 (3)	0.6963 (2)	0.0618 (9)
H11	0.5216	0.8119	0.7560	0.074*
C12	0.4614 (2)	0.9394 (3)	0.6635 (2)	0.0592 (9)
H12	0.4741	1.0116	0.7008	0.071*
C13	0.2532 (2)	0.4353 (2)	0.36398 (18)	0.0423 (6)
C14	0.20479 (18)	0.3495 (2)	0.28849 (16)	0.0378 (6)
C15	0.2531 (2)	0.3170 (2)	0.21885 (17)	0.0437 (7)
H15	0.3153	0.3474	0.2215	0.052*
C16	0.2121 (2)	0.2417 (3)	0.14645 (18)	0.0502 (7)
H16	0.2463	0.2210	0.1012	0.060*
C17	0.1199 (2)	0.1976 (3)	0.14189 (19)	0.0556 (8)
H17	0.0913	0.1468	0.0931	0.067*
C18	0.0694 (2)	0.2279 (3)	0.2089 (2)	0.0560 (8)
H18	0.0068	0.1982	0.2042	0.067*
C19	0.1104 (2)	0.3023 (2)	0.28385 (19)	0.0465 (7)
C20	−0.00863 (19)	0.2604 (3)	0.38439 (19)	0.0488 (7)
C21	−0.0202 (2)	0.1287 (3)	0.3698 (2)	0.0632 (9)
H21	0.0167	0.0857	0.3340	0.076*
C22	−0.0867 (2)	0.0609 (3)	0.4082 (2)	0.0725 (10)
H22	−0.0947	−0.0273	0.3975	0.087*
C23	−0.1407 (2)	0.1224 (4)	0.4619 (2)	0.0719 (10)
H23	−0.1853	0.0761	0.4872	0.086*
C24	−0.1289 (2)	0.2532 (3)	0.4784 (2)	0.0618 (9)
H24	−0.1643	0.2949	0.5161	0.074*
C25	−0.0646 (2)	0.3212 (3)	0.43881 (19)	0.0516 (7)
H25	−0.0583	0.4098	0.4485	0.062*
N1	0.42259 (14)	0.72155 (19)	0.55568 (13)	0.0364 (5)
N2	0.33596 (14)	0.7321 (2)	0.38417 (14)	0.0389 (5)
O1	0.34218 (12)	0.45837 (16)	0.36536 (12)	0.0441 (4)
O2	0.20849 (14)	0.48232 (18)	0.41969 (14)	0.0598 (6)
Cl1	0.43055 (5)	0.41708 (6)	0.56938 (4)	0.04377 (17)
N3	0.05935 (19)	0.3350 (2)	0.35103 (18)	0.0620 (8)
H3N	0.090 (2)	0.397 (3)	0.389 (2)	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.04285 (19)	0.02743 (17)	0.03428 (18)	−0.00175 (14)	0.00194 (13)	−0.00253 (13)
C1	0.0589 (19)	0.058 (2)	0.0487 (18)	0.0005 (15)	−0.0022 (15)	0.0070 (15)
C2	0.081 (3)	0.091 (3)	0.051 (2)	0.012 (2)	−0.0102 (18)	0.025 (2)
C3	0.076 (2)	0.067 (2)	0.081 (3)	0.015 (2)	0.006 (2)	0.035 (2)
C4	0.0479 (17)	0.0423 (17)	0.068 (2)	0.0088 (14)	0.0174 (15)	0.0180 (15)
C5	0.0344 (14)	0.0360 (16)	0.0454 (16)	0.0014 (12)	0.0123 (12)	0.0065 (12)
C6	0.070 (2)	0.0270 (16)	0.102 (3)	0.0102 (15)	0.034 (2)	0.0123 (17)
C7	0.067 (2)	0.0284 (16)	0.096 (3)	−0.0064 (15)	0.037 (2)	−0.0112 (17)
C8	0.0443 (16)	0.0332 (15)	0.066 (2)	−0.0051 (12)	0.0230 (15)	−0.0121 (14)
C9	0.0358 (14)	0.0302 (14)	0.0448 (15)	−0.0009 (11)	0.0135 (12)	−0.0032 (11)
C10	0.0628 (19)	0.0461 (17)	0.0387 (16)	0.0081 (14)	0.0005 (14)	−0.0069 (13)
C11	0.072 (2)	0.068 (2)	0.0414 (17)	0.0049 (18)	0.0004 (15)	−0.0214 (16)
C12	0.061 (2)	0.056 (2)	0.061 (2)	−0.0064 (16)	0.0123 (16)	−0.0331 (16)
C13	0.0507 (17)	0.0294 (14)	0.0457 (16)	−0.0048 (13)	0.0060 (13)	−0.0034 (12)
C14	0.0416 (15)	0.0302 (14)	0.0390 (15)	−0.0044 (11)	0.0009 (12)	−0.0004 (11)
C15	0.0470 (16)	0.0391 (16)	0.0428 (16)	−0.0031 (13)	0.0031 (13)	0.0001 (13)
C16	0.063 (2)	0.0471 (17)	0.0391 (16)	−0.0008 (15)	0.0070 (14)	−0.0035 (13)
C17	0.067 (2)	0.0500 (18)	0.0421 (17)	−0.0128 (15)	−0.0092 (15)	−0.0066 (14)
C18	0.0500 (18)	0.060 (2)	0.0540 (19)	−0.0205 (15)	0.0002 (15)	−0.0107 (15)
C19	0.0496 (17)	0.0396 (16)	0.0496 (17)	−0.0097 (13)	0.0078 (14)	−0.0030 (13)
C20	0.0397 (16)	0.0508 (18)	0.0544 (18)	−0.0098 (14)	0.0056 (13)	−0.0066 (14)
C21	0.064 (2)	0.0524 (19)	0.081 (2)	−0.0103 (16)	0.0342 (18)	−0.0120 (17)
C22	0.079 (2)	0.051 (2)	0.091 (3)	−0.0184 (18)	0.026 (2)	−0.0093 (18)
C23	0.058 (2)	0.081 (3)	0.084 (3)	−0.0147 (19)	0.0313 (19)	0.001 (2)
C24	0.051 (2)	0.072 (2)	0.064 (2)	0.0018 (17)	0.0158 (16)	−0.0056 (17)
C25	0.0470 (17)	0.0515 (18)	0.0541 (18)	−0.0023 (14)	0.0039 (14)	−0.0076 (14)
N1	0.0443 (13)	0.0316 (12)	0.0330 (12)	0.0019 (10)	0.0060 (10)	−0.0032 (9)
N2	0.0399 (12)	0.0388 (13)	0.0358 (12)	−0.0010 (10)	0.0016 (10)	0.0026 (10)
O1	0.0398 (11)	0.0433 (11)	0.0462 (11)	−0.0080 (8)	0.0009 (8)	−0.0105 (8)
O2	0.0577 (13)	0.0571 (13)	0.0682 (14)	−0.0152 (10)	0.0209 (11)	−0.0282 (11)
Cl1	0.0519 (4)	0.0330 (3)	0.0466 (4)	−0.0034 (3)	0.0096 (3)	0.0086 (3)
N3	0.0609 (17)	0.0593 (18)	0.0713 (19)	−0.0270 (14)	0.0264 (14)	−0.0223 (14)

Geometric parameters (Å, º) top

Cu1—O1	1.9423 (16)	C12—H12	0.9300
Cu1—N1	2.0241 (19)	C13—O2	1.239 (3)
Cu1—N2	2.045 (2)	C13—O1	1.279 (3)
Cu1—Cl1	2.3010 (7)	C13—C14	1.500 (3)
Cu1—O2	2.700 (2)	C14—C15	1.393 (3)
Cu1—Cl1ⁱ	2.7011 (8)	C14—C19	1.413 (3)
C1—N2	1.326 (3)	C15—C16	1.373 (3)
C1—C2	1.388 (4)	C15—H15	0.9300
C1—H1	0.9300	C16—C17	1.374 (4)
C2—C3	1.359 (5)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.374 (4)
C3—C4	1.395 (4)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.396 (4)
C4—C5	1.402 (3)	C18—H18	0.9300
C4—C6	1.433 (4)	C19—N3	1.388 (3)
C5—N2	1.361 (3)	C20—C21	1.386 (4)
C5—C9	1.423 (3)	C20—C25	1.391 (4)
C6—C7	1.345 (4)	C20—N3	1.399 (3)
C6—H6	0.9300	C21—C22	1.384 (4)
C7—C8	1.424 (4)	C21—H21	0.9300
C7—H7	0.9300	C22—C23	1.367 (4)
C8—C12	1.396 (4)	C22—H22	0.9300
C8—C9	1.400 (3)	C23—C24	1.382 (4)
C9—N1	1.361 (3)	C23—H23	0.9300
C10—N1	1.322 (3)	C24—C25	1.372 (4)
C10—C11	1.389 (4)	C24—H24	0.9300
C10—H10	0.9300	C25—H25	0.9300
C11—C12	1.350 (4)	Cl1—Cu1ⁱ	2.7011 (8)
C11—H11	0.9300	N3—H3N	0.91 (3)

O1—Cu1—N1	171.49 (8)	O2—C13—O1	122.9 (2)
O1—Cu1—N2	91.26 (8)	O2—C13—C14	121.5 (2)
O2—Cu1—N1	121.94 (6)	O1—C13—C14	115.6 (2)
O2—Cu1—N2	85.45 (8)	C15—C14—C19	118.3 (2)
N1—Cu1—N2	80.73 (8)	C15—C14—C13	119.3 (2)
O1—Cu1—Cl1	93.86 (6)	C19—C14—C13	122.4 (2)
O2—Cu1—Cl1	90.70 (6)	C16—C15—C14	122.4 (3)
N1—Cu1—Cl1	93.65 (6)	C16—C15—H15	118.8
N2—Cu1—Cl1	170.08 (6)	C14—C15—H15	118.8
O1—Cu1—Cl1ⁱ	94.02 (6)	C15—C16—C17	119.0 (3)
O2—Cu1—Cl1ⁱ	147.97 (6)	C15—C16—H16	120.5
N1—Cu1—Cl1ⁱ	89.91 (6)	C17—C16—H16	120.5
N2—Cu1—Cl1ⁱ	97.64 (6)	C18—C17—C16	120.5 (3)
Cl1—Cu1—Cl1ⁱ	90.47 (2)	C18—C17—H17	119.7
O1—Cu1—O2	53.97 (7)	C16—C17—H17	119.7
N2—C1—C2	122.2 (3)	C17—C18—C19	121.4 (3)
N2—C1—H1	118.9	C17—C18—H18	119.3
C2—C1—H1	118.9	C19—C18—H18	119.3
C3—C2—C1	120.1 (3)	N3—C19—C18	121.7 (3)
C3—C2—H2	119.9	N3—C19—C14	119.8 (2)
C1—C2—H2	119.9	C18—C19—C14	118.5 (3)
C2—C3—C4	119.9 (3)	C21—C20—C25	118.3 (3)
C2—C3—H3	120.0	C21—C20—N3	123.8 (3)
C4—C3—H3	120.0	C25—C20—N3	117.8 (3)
C3—C4—C5	116.5 (3)	C22—C21—C20	120.2 (3)
C3—C4—C6	125.4 (3)	C22—C21—H21	119.9
C5—C4—C6	118.0 (3)	C20—C21—H21	119.9
N2—C5—C4	123.5 (3)	C23—C22—C21	120.6 (3)
N2—C5—C9	116.3 (2)	C23—C22—H22	119.7
C4—C5—C9	120.2 (2)	C21—C22—H22	119.7
C7—C6—C4	121.4 (3)	C22—C23—C24	120.0 (3)
C7—C6—H6	119.3	C22—C23—H23	120.0
C4—C6—H6	119.3	C24—C23—H23	120.0
C6—C7—C8	121.6 (3)	C25—C24—C23	119.5 (3)
C6—C7—H7	119.2	C25—C24—H24	120.2
C8—C7—H7	119.2	C23—C24—H24	120.2
C12—C8—C9	116.7 (3)	C24—C25—C20	121.3 (3)
C12—C8—C7	125.1 (3)	C24—C25—H25	119.3
C9—C8—C7	118.2 (3)	C20—C25—H25	119.3
N1—C9—C8	122.9 (2)	C10—N1—C9	117.8 (2)
N1—C9—C5	116.6 (2)	C10—N1—Cu1	128.62 (18)
C8—C9—C5	120.5 (2)	C9—N1—Cu1	113.47 (16)
N1—C10—C11	122.6 (3)	C1—N2—C5	117.7 (2)
N1—C10—H10	118.7	C1—N2—Cu1	129.35 (19)
C11—C10—H10	118.7	C5—N2—Cu1	112.90 (16)
C12—C11—C10	119.6 (3)	C13—O1—Cu1	108.82 (16)
C12—C11—H11	120.2	Cu1—Cl1—Cu1ⁱ	89.53 (2)
C10—C11—H11	120.2	C19—N3—C20	127.8 (2)
C11—C12—C8	120.3 (3)	C19—N3—H3N	112 (2)
C11—C12—H12	119.9	C20—N3—H3N	116 (2)
C8—C12—H12	119.9

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O2	0.91 (3)	1.88 (3)	2.652 (3)	142 (3)

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₃H₁₀NO₂)₂Cl₂(C₁₂H₈N₂)₂]
M_r	982.83
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.1685 (18), 10.3545 (13), 14.9955 (19)
β (°)	100.843 (2)
V (Å³)	2160.7 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.16
Crystal size (mm)	0.40 × 0.32 × 0.28

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.643, 0.718
No. of measured, independent and observed [I > 2σ(I)] reflections	12962, 5099, 3284
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.092, 1.03
No. of reflections	5099
No. of parameters	292
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.46

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990), SHELXL97.

Selected geometric parameters (Å, º) top

Cu1—O1	1.9423 (16)	Cu1—Cl1	2.3010 (7)
Cu1—N1	2.0241 (19)	Cu1—O2	2.700 (2)
Cu1—N2	2.045 (2)	Cu1—Cl1ⁱ	2.7011 (8)

O1—Cu1—N1	171.49 (8)	N2—Cu1—Cl1	170.08 (6)
O1—Cu1—N2	91.26 (8)	O1—Cu1—Cl1ⁱ	94.02 (6)
O2—Cu1—N1	121.94 (6)	O2—Cu1—Cl1ⁱ	147.97 (6)
O2—Cu1—N2	85.45 (8)	N1—Cu1—Cl1ⁱ	89.91 (6)
N1—Cu1—N2	80.73 (8)	N2—Cu1—Cl1ⁱ	97.64 (6)
O1—Cu1—Cl1	93.86 (6)	Cl1—Cu1—Cl1ⁱ	90.47 (2)
O2—Cu1—Cl1	90.70 (6)	O1—Cu1—O2	53.97 (7)
N1—Cu1—Cl1	93.65 (6)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O2	0.91 (3)	1.88 (3)	2.652 (3)	142 (3)

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