Bis[(1H-1,2,3-benzotriazol-1-yl)methyl 2,2-dimethyl-propano-ato-κN(3)]dichlorido-copper(II).

In the title compound, [CuCl(2)(C(12)H(15)N(3)O(2))(2)], the Cu(II) ion is located on an inversion center and is four-coordinated in a distorted square-planar geometry by two chloride anions and two N atoms from two (1H-1,2,3-benzotriazol-1-yl)methyl 2,2-dimethyl-propano-ate ligands. The Cl-Cu-N angles of 90.55 (9) and 89.45 (9)° are close to ideal values. In the crystal, weak π-π stacking inter-actions are observed between inversion-related benzene rings [centroid-centroid distance = 4.0028 (6) Å].

Related literature

For related structures, see: Wang (2008 ▶); Tang et al. (2011 ▶). For the structure of the free benzotriazole ligand, see: Xu & Shen (2012 ▶).

Experimental

Crystal data

[CuCl2(C12H15N3O2)2]

M = 600.98

Monoclinic,

a = 10.1929 (19) Å

b = 14.576 (2) Å

c = 9.2565 (15) Å

β = 96.499 (14)°

V = 1366.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.04 mm−1

T = 296 K

0.20 × 0.20 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.820, T max = 0.828

9798 measured reflections

2412 independent reflections

2025 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.101

S = 1.15

2412 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.39 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: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015486/bh2425sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015486/bh2425Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[CuCl2(C12H15N3O2)2]	F(000) = 622
Mr = 600.98	Dx = 1.461 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3200 reflections
a = 10.1929 (19) Å	θ = 2.5–26.6°
b = 14.576 (2) Å	µ = 1.04 mm−1
c = 9.2565 (15) Å	T = 296 K
β = 96.499 (14)°	Block, blue
V = 1366.4 (4) Å3	0.20 × 0.20 × 0.19 mm
Z = 2

Bruker SMART APEX CCD area-detector diffractometer	2412 independent reflections
Radiation source: fine-focus sealed tube	2025 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 10.0 pixels mm-1	θmax = 25.0°, θmin = 2.0°
φ and ω scans	h = −11→12
Absorption correction: multi-scan (SABADS; Sheldrick, 1996)	k = −17→17
Tmin = 0.820, Tmax = 0.828	l = −10→11
9798 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0095P)2 + 1.8659P] where P = (Fo2 + 2Fc2)/3
2412 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.39 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C1	0.3811 (3)	−0.0246 (3)	0.2886 (4)	0.0350 (8)
C2	0.3663 (4)	−0.1197 (3)	0.2948 (4)	0.0413 (9)
H2	0.3859	−0.1575	0.2192	0.050*
C3	0.3216 (4)	−0.1545 (3)	0.4170 (4)	0.0488 (10)
H3	0.3111	−0.2176	0.4246	0.059*
C4	0.2909 (4)	−0.0983 (3)	0.5317 (4)	0.0503 (11)
H4	0.2610	−0.1253	0.6129	0.060*
C5	0.3036 (4)	−0.0055 (3)	0.5273 (4)	0.0459 (10)
H5	0.2829	0.0320	0.6028	0.055*
C6	0.3496 (3)	0.0301 (3)	0.4023 (4)	0.0350 (8)
C7	0.3690 (4)	0.2011 (3)	0.4420 (4)	0.0436 (10)
H7A	0.4024	0.1906	0.5430	0.052*
H7B	0.4236	0.2477	0.4037	0.052*
C8	0.2046 (4)	0.3077 (3)	0.3507 (4)	0.0442 (10)
C9	0.0678 (4)	0.3415 (3)	0.3700 (4)	0.0441 (10)
C10	−0.0319 (4)	0.2630 (3)	0.3583 (6)	0.0661 (14)
H10A	−0.0393	0.2379	0.2619	0.099*
H10B	−0.1165	0.2857	0.3783	0.099*
H10C	−0.0029	0.2161	0.4274	0.099*
C11	0.0769 (4)	0.3834 (3)	0.5231 (5)	0.0570 (12)
H11A	0.1074	0.3378	0.5937	0.085*
H11B	−0.0088	0.4047	0.5417	0.085*
H11C	0.1375	0.4340	0.5294	0.085*
C12	0.0271 (5)	0.4150 (3)	0.2566 (5)	0.0610 (13)
H12A	0.0880	0.4654	0.2690	0.092*
H12B	−0.0602	0.4363	0.2683	0.092*
H12C	0.0279	0.3895	0.1611	0.092*
Cl1	0.31996 (11)	−0.08447 (8)	−0.06653 (11)	0.0563 (3)
Cu1	0.5000	0.0000	0.0000	0.03856 (19)
N1	0.4260 (3)	0.0325 (2)	0.1866 (3)	0.0398 (8)
N2	0.4237 (3)	0.1178 (2)	0.2304 (3)	0.0414 (8)
N3	0.3767 (3)	0.1173 (2)	0.3608 (3)	0.0375 (7)
O1	0.2367 (3)	0.23282 (18)	0.4335 (3)	0.0461 (7)
O2	0.2812 (3)	0.3406 (2)	0.2781 (4)	0.0846 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0313 (19)	0.040 (2)	0.0332 (19)	0.0021 (16)	0.0034 (15)	−0.0014 (16)
C2	0.042 (2)	0.043 (2)	0.038 (2)	0.0008 (18)	0.0036 (17)	−0.0064 (18)
C3	0.048 (2)	0.047 (3)	0.049 (2)	−0.005 (2)	−0.0013 (19)	0.005 (2)
C4	0.052 (3)	0.060 (3)	0.040 (2)	−0.010 (2)	0.0068 (19)	0.007 (2)
C5	0.045 (2)	0.057 (3)	0.037 (2)	0.000 (2)	0.0082 (17)	−0.003 (2)
C6	0.032 (2)	0.041 (2)	0.033 (2)	0.0044 (17)	0.0076 (15)	−0.0002 (17)
C7	0.039 (2)	0.043 (2)	0.049 (2)	0.0064 (18)	0.0088 (18)	−0.0093 (19)
C8	0.053 (3)	0.041 (2)	0.040 (2)	0.001 (2)	0.0164 (19)	0.0003 (19)
C9	0.044 (2)	0.041 (2)	0.049 (2)	0.0072 (19)	0.0108 (18)	0.0018 (19)
C10	0.047 (3)	0.061 (3)	0.092 (4)	0.000 (2)	0.014 (3)	0.004 (3)
C11	0.061 (3)	0.057 (3)	0.056 (3)	0.020 (2)	0.020 (2)	0.000 (2)
C12	0.062 (3)	0.064 (3)	0.057 (3)	0.018 (2)	0.007 (2)	0.009 (2)
Cl1	0.0553 (7)	0.0696 (8)	0.0458 (6)	−0.0151 (6)	0.0141 (5)	−0.0123 (5)
Cu1	0.0461 (4)	0.0381 (4)	0.0336 (4)	0.0010 (3)	0.0136 (3)	−0.0033 (3)
N1	0.0450 (19)	0.0386 (19)	0.0374 (18)	0.0017 (15)	0.0107 (14)	−0.0057 (15)
N2	0.046 (2)	0.041 (2)	0.0382 (18)	0.0028 (15)	0.0132 (15)	−0.0009 (15)
N3	0.0396 (18)	0.0411 (19)	0.0328 (16)	0.0078 (15)	0.0087 (13)	−0.0043 (14)
O1	0.0432 (16)	0.0388 (16)	0.0592 (17)	0.0125 (13)	0.0189 (13)	0.0043 (14)
O2	0.078 (2)	0.085 (3)	0.102 (3)	0.034 (2)	0.054 (2)	0.048 (2)

C1—N1	1.375 (5)	C9—C12	1.524 (5)
C1—C6	1.386 (5)	C9—C10	1.526 (6)
C1—C2	1.396 (5)	C9—C11	1.536 (5)
C2—C3	1.364 (5)	C10—H10A	0.9600
C2—H2	0.9300	C10—H10B	0.9600
C3—C4	1.404 (6)	C10—H10C	0.9600
C3—H3	0.9300	C11—H11A	0.9600
C4—C5	1.360 (6)	C11—H11B	0.9600
C4—H4	0.9300	C11—H11C	0.9600
C5—C6	1.397 (5)	C12—H12A	0.9600
C5—H5	0.9300	C12—H12B	0.9600
C6—N3	1.365 (5)	C12—H12C	0.9600
C7—O1	1.418 (4)	Cl1—Cu1	2.2377 (11)
C7—N3	1.442 (5)	Cu1—N1i	2.018 (3)
C7—H7A	0.9700	Cu1—N1	2.018 (3)
C7—H7B	0.9700	Cu1—Cl1i	2.2377 (11)
C8—O2	1.188 (5)	N1—N2	1.309 (4)
C8—O1	1.352 (5)	N2—N3	1.347 (4)
C8—C9	1.508 (5)
N1—C1—C6	107.3 (3)	C9—C10—H10A	109.5
N1—C1—C2	132.4 (3)	C9—C10—H10B	109.5
C6—C1—C2	120.3 (4)	H10A—C10—H10B	109.5
C3—C2—C1	116.8 (4)	C9—C10—H10C	109.5
C3—C2—H2	121.6	H10A—C10—H10C	109.5
C1—C2—H2	121.6	H10B—C10—H10C	109.5
C2—C3—C4	122.3 (4)	C9—C11—H11A	109.5
C2—C3—H3	118.8	C9—C11—H11B	109.5
C4—C3—H3	118.8	H11A—C11—H11B	109.5
C5—C4—C3	121.8 (4)	C9—C11—H11C	109.5
C5—C4—H4	119.1	H11A—C11—H11C	109.5
C3—C4—H4	119.1	H11B—C11—H11C	109.5
C4—C5—C6	115.9 (4)	C9—C12—H12A	109.5
C4—C5—H5	122.1	C9—C12—H12B	109.5
C6—C5—H5	122.1	H12A—C12—H12B	109.5
N3—C6—C1	104.5 (3)	C9—C12—H12C	109.5
N3—C6—C5	132.6 (4)	H12A—C12—H12C	109.5
C1—C6—C5	122.9 (4)	H12B—C12—H12C	109.5
O1—C7—N3	110.8 (3)	N1i—Cu1—N1	180.0
O1—C7—H7A	109.5	N1i—Cu1—Cl1	90.55 (9)
N3—C7—H7A	109.5	N1—Cu1—Cl1	89.45 (9)
O1—C7—H7B	109.5	N1i—Cu1—Cl1i	89.45 (9)
N3—C7—H7B	109.5	N1—Cu1—Cl1i	90.55 (9)
H7A—C7—H7B	108.1	Cl1—Cu1—Cl1i	180.0
O2—C8—O1	121.0 (4)	N2—N1—C1	110.1 (3)
O2—C8—C9	127.6 (4)	N2—N1—Cu1	120.7 (2)
O1—C8—C9	111.4 (3)	C1—N1—Cu1	129.1 (3)
C8—C9—C12	109.3 (3)	N1—N2—N3	107.0 (3)
C8—C9—C10	111.4 (3)	N2—N3—C6	111.2 (3)
C12—C9—C10	110.5 (4)	N2—N3—C7	120.5 (3)
C8—C9—C11	106.3 (3)	C6—N3—C7	128.1 (3)
C12—C9—C11	109.8 (3)	C8—O1—C7	117.5 (3)
C10—C9—C11	109.5 (4)
N1—C1—C2—C3	178.1 (4)	C6—C1—N1—Cu1	175.6 (2)
C6—C1—C2—C3	−0.8 (5)	C2—C1—N1—Cu1	−3.4 (6)
C1—C2—C3—C4	0.4 (6)	Cl1—Cu1—N1—N2	−131.5 (3)
C2—C3—C4—C5	0.2 (6)	Cl1i—Cu1—N1—N2	48.5 (3)
C3—C4—C5—C6	−0.3 (6)	Cl1—Cu1—N1—C1	53.3 (3)
N1—C1—C6—N3	0.4 (4)	Cl1i—Cu1—N1—C1	−126.7 (3)
C2—C1—C6—N3	179.5 (3)	C1—N1—N2—N3	−0.3 (4)
N1—C1—C6—C5	−178.4 (3)	Cu1—N1—N2—N3	−176.4 (2)
C2—C1—C6—C5	0.7 (6)	N1—N2—N3—C6	0.6 (4)
C4—C5—C6—N3	−178.6 (4)	N1—N2—N3—C7	176.6 (3)
C4—C5—C6—C1	−0.1 (6)	C1—C6—N3—N2	−0.6 (4)
O2—C8—C9—C12	12.0 (6)	C5—C6—N3—N2	178.0 (4)
O1—C8—C9—C12	−170.4 (3)	C1—C6—N3—C7	−176.2 (3)
O2—C8—C9—C10	134.4 (5)	C5—C6—N3—C7	2.5 (7)
O1—C8—C9—C10	−48.0 (5)	O1—C7—N3—N2	104.3 (4)
O2—C8—C9—C11	−106.5 (5)	O1—C7—N3—C6	−80.5 (5)
O1—C8—C9—C11	71.2 (4)	O2—C8—O1—C7	6.4 (6)
C6—C1—N1—N2	0.0 (4)	C9—C8—O1—C7	−171.4 (3)
C2—C1—N1—N2	−179.0 (4)	N3—C7—O1—C8	−107.4 (4)