Chlorido(10,11,12,13-tetra­hydro-4,5,9,14-tetra­aza­benzo[b]triphenyl­ene-κ2N4,N5)copper(I)

Hong, J.; Li, X.-Y.; Ng, S.W.

doi:10.1107/S1600536811034817

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1322

doi:10.1107/S1600536811034817

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Chlorido(10,11,12,13-tetrahydro-4,5,9,14-tetraazabenzo[b]triphenylene-κ²N⁴,N⁵)copper(I)

Jun Hong,^a Xiu-Ying Li ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Chemistry, Jilin Normal University, Siping 136000, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 24 August 2011; accepted 25 August 2011; online 31 August 2011)

The Cu^I atom in the title compound, [CuCl(C₁₈H₁₄N₄)], is N,N′-chelated by the N-heterocyclic ligand and coordinated by one Cl⁻ anion in a distorted trigonal geometry. In the crystal, the Cu^I atom is disordered over two positions in a 0.667 (6):0.333 (6) ratio. The deviation of the Cu atom from the N/N/Cl coordination plane is 0.013 (3) Å for the major component and 0.073 (6) Å for the minor component. Two methylene C atoms are also disordered over two positions in a 0.667 (6):0.333 (6) ratio.

Related literature

For the synthesis of the N-heterocyclic ligand, see: Che et al. (2006 ).

Experimental

Crystal data

[CuCl(C₁₈H₁₄N₄)]
M_r = 385.32
Monoclinic, P 2₁ /c
a = 7.9405 (10) Å
b = 15.8861 (19) Å
c = 12.6312 (16) Å
β = 99.531 (2)°
V = 1571.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.57 mm⁻¹
T = 293 K
0.15 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.799, T_max = 0.859
8464 measured reflections
3064 independent reflections
1957 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.119
S = 0.99
3064 reflections
233 parameters
16 restraints
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—Cl1	2.102 (3)
Cu1—N1	1.928 (4)
Cu1—N2	2.236 (4)
Cu1′—Cl1	2.112 (6)
Cu1′—N1	2.268 (7)
Cu1′—N2	1.858 (6)

Data collection: APEX2 (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811034817/xu5308sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034817/xu5308Isup2.hkl

checkCIF report

Comment top

There is extensive literature on the chelating ability of 1,10-phenanthroline and its derivatives. The N-heterocycle, 10,11,12,13-tetrahydro-4,5,9,14-tetraazabenzo[b]triphenylene, is a new addition to this class of chelates. It reacts with copper(II) chloride under hydrothermal conditions to yield a 1:1 copper(I) chloride adduct (Scheme I). The Cu^I atom is N,N'-chelated by the N-heterocycle, and it shows trigonal coordination. The atom lies on the trigonal plane defined by the two chelating N atoms and the chlorine atom (Fig. 1). The aromatic ring system is planar; however, the N-heterocycle is buckled in the region of the cyclohexene part owing to the sp³ nature of the methylene C atoms.

Related literature top

For the synthesis of the N-heterocyclic ligand, see: Che et al. (2006).

Experimental top

The N-heterocycle was synthesized according to a literature method (Che et al., 2006). To a copper(II) chloride dihydrate (0.5 mmol), the ligand (0.5 mmol) and water (5 ml) was added triethylamine to a final pH of 5.5. The mixture was heated in a Teflon-lined, stainless-steel Paar bomb at 423 K for 3 days. The Parr bomb was then cooled slowly; yellow blocks were isolated by hand.

Computing details top

Data collection: APEX (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of CuCl(C₁₈H₁₄N₄) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.

Chlorido(10,11,12,13-tetrahydro-4,5,9,14-tetraazabenzo[b]triphenylene- κ²N⁴,N⁵)copper(I) top

Crystal data top

[CuCl(C₁₈H₁₄N₄)]	F(000) = 784
M_r = 385.32	D_x = 1.629 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1330 reflections
a = 7.9405 (10) Å	θ = 2.6–21.7°
b = 15.8861 (19) Å	µ = 1.57 mm⁻¹
c = 12.6312 (16) Å	T = 293 K
β = 99.531 (2)°	Prism, yellow
V = 1571.4 (3) Å³	0.15 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	3064 independent reflections
Radiation source: fine-focus sealed tube	1957 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.799, T_max = 0.859	k = −19→11
8464 measured reflections	l = −15→15

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0591P)²] where P = (F_o² + 2F_c²)/3
3064 reflections	(Δ/σ)_max = 0.001
233 parameters	Δρ_max = 0.26 e Å⁻³
16 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[CuCl(C₁₈H₁₄N₄)]	V = 1571.4 (3) Å³
M_r = 385.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9405 (10) Å	µ = 1.57 mm⁻¹
b = 15.8861 (19) Å	T = 293 K
c = 12.6312 (16) Å	0.15 × 0.10 × 0.10 mm
β = 99.531 (2)°

Data collection top

Bruker SMART APEX diffractometer	3064 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1957 reflections with I > 2σ(I)
T_min = 0.799, T_max = 0.859	R_int = 0.036
8464 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	16 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 0.99	Δρ_max = 0.26 e Å⁻³
3064 reflections	Δρ_min = −0.34 e Å⁻³
233 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.5949 (4)	0.27795 (17)	0.5683 (2)	0.0588 (5)	0.667 (6)
Cu1'	0.6063 (7)	0.2766 (4)	0.5259 (5)	0.0618 (10)	0.333 (6)
Cl1	0.54512 (13)	0.14874 (5)	0.54499 (7)	0.0650 (3)
N1	0.6098 (3)	0.38256 (15)	0.6466 (2)	0.0497 (7)
N2	0.6947 (3)	0.36198 (16)	0.4508 (2)	0.0500 (7)
N3	0.7722 (3)	0.67671 (15)	0.64582 (18)	0.0409 (6)
N4	0.8683 (3)	0.65335 (15)	0.44444 (18)	0.0411 (6)
C1	0.5643 (4)	0.3927 (2)	0.7432 (3)	0.0567 (9)
H1	0.5231	0.3463	0.7759	0.068*
C2	0.5758 (4)	0.4695 (2)	0.7973 (3)	0.0538 (8)
H2	0.5426	0.4738	0.8643	0.065*
C3	0.6361 (4)	0.5382 (2)	0.7512 (2)	0.0479 (8)
H3	0.6440	0.5898	0.7862	0.058*
C4	0.6863 (4)	0.53036 (18)	0.6501 (2)	0.0392 (7)
C5	0.7535 (3)	0.60072 (18)	0.5960 (2)	0.0381 (7)
C6	0.8016 (3)	0.58937 (18)	0.4953 (2)	0.0365 (7)
C7	0.7847 (3)	0.50718 (18)	0.4442 (2)	0.0392 (7)
C8	0.8325 (4)	0.49183 (19)	0.3433 (2)	0.0478 (8)
H8	0.8795	0.5347	0.3073	0.057*
C9	0.8091 (4)	0.4130 (2)	0.2986 (3)	0.0560 (9)
H9	0.8403	0.4016	0.2322	0.067*
C10	0.7377 (4)	0.3504 (2)	0.3545 (3)	0.0584 (9)
H10	0.7190	0.2977	0.3228	0.070*
C11	0.7182 (4)	0.43948 (18)	0.4953 (2)	0.0416 (7)
C12	0.6714 (4)	0.45138 (18)	0.6012 (2)	0.0410 (7)
C13	0.8372 (4)	0.73873 (17)	0.5965 (2)	0.0396 (7)
C14	0.8849 (4)	0.72754 (17)	0.4930 (2)	0.0399 (7)
C15	0.9599 (4)	0.79779 (18)	0.4360 (2)	0.0517 (8)
H15A	0.8991	0.8009	0.3629	0.062*	0.667 (6)
H15B	1.0781	0.7843	0.4327	0.062*	0.667 (6)
H15C	0.8721	0.8206	0.3810	0.062*	0.333 (6)
H15D	1.0498	0.7752	0.4008	0.062*	0.333 (6)
C16	0.9535 (7)	0.8843 (3)	0.4885 (4)	0.0508 (16)	0.667 (6)
H16A	0.8399	0.9079	0.4697	0.061*	0.667 (6)
H16B	1.0335	0.9221	0.4624	0.061*	0.667 (6)
C17	0.9997 (7)	0.8754 (3)	0.6111 (4)	0.0549 (16)	0.667 (6)
H17A	1.1104	0.8486	0.6296	0.066*	0.667 (6)
H17B	1.0059	0.9306	0.6443	0.066*	0.667 (6)
C16'	1.0331 (12)	0.8687 (5)	0.5113 (7)	0.0508 (16)	0.33
H16C	1.1404	0.8506	0.5533	0.061*	0.333 (6)
H16D	1.0559	0.9172	0.4692	0.061*	0.333 (6)
C17'	0.9110 (14)	0.8937 (4)	0.5862 (7)	0.0549 (16)	0.33
H17C	0.9632	0.9378	0.6338	0.066*	0.333 (6)
H17D	0.8080	0.9166	0.5440	0.066*	0.333 (6)
C18	0.8636 (5)	0.82230 (19)	0.6522 (2)	0.0569 (9)
H18A	0.8972	0.8131	0.7287	0.068*	0.667 (6)
H18B	0.7565	0.8530	0.6414	0.068*	0.667 (6)
H18C	0.7592	0.8372	0.6783	0.068*	0.333 (6)
H18D	0.9525	0.8160	0.7143	0.068*	0.333 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0555 (6)	0.0341 (5)	0.0832 (13)	−0.0029 (4)	0.0005 (9)	0.0019 (9)
Cu1'	0.0573 (12)	0.0405 (11)	0.085 (3)	−0.0055 (8)	0.004 (2)	0.009 (2)
Cl1	0.0841 (7)	0.0418 (5)	0.0688 (6)	−0.0144 (4)	0.0114 (5)	0.0013 (4)
N1	0.0432 (15)	0.0390 (16)	0.0676 (18)	0.0012 (12)	0.0107 (14)	0.0075 (14)
N2	0.0509 (16)	0.0357 (15)	0.0606 (18)	0.0034 (12)	0.0012 (14)	−0.0063 (13)
N3	0.0453 (14)	0.0362 (14)	0.0418 (14)	−0.0020 (11)	0.0089 (11)	0.0008 (12)
N4	0.0440 (15)	0.0365 (15)	0.0424 (14)	−0.0003 (11)	0.0059 (11)	0.0005 (12)
C1	0.049 (2)	0.047 (2)	0.077 (2)	0.0021 (16)	0.0190 (18)	0.0199 (19)
C2	0.053 (2)	0.056 (2)	0.056 (2)	0.0043 (17)	0.0174 (16)	0.0070 (18)
C3	0.0487 (19)	0.0446 (19)	0.0511 (19)	−0.0014 (15)	0.0101 (15)	−0.0003 (16)
C4	0.0343 (16)	0.0392 (18)	0.0426 (18)	0.0016 (13)	0.0020 (13)	0.0017 (14)
C5	0.0357 (16)	0.0355 (16)	0.0421 (17)	0.0003 (13)	0.0033 (13)	0.0002 (14)
C6	0.0333 (15)	0.0341 (16)	0.0404 (17)	0.0011 (12)	0.0008 (13)	0.0002 (13)
C7	0.0349 (16)	0.0368 (17)	0.0431 (17)	0.0041 (13)	−0.0014 (13)	−0.0006 (14)
C8	0.055 (2)	0.0420 (19)	0.0451 (18)	0.0063 (15)	0.0041 (15)	−0.0017 (15)
C9	0.064 (2)	0.052 (2)	0.050 (2)	0.0103 (17)	0.0035 (17)	−0.0109 (17)
C10	0.065 (2)	0.039 (2)	0.066 (2)	0.0043 (17)	−0.0037 (19)	−0.0141 (18)
C11	0.0380 (16)	0.0367 (17)	0.0467 (18)	0.0047 (13)	−0.0025 (14)	−0.0018 (15)
C12	0.0320 (15)	0.0346 (17)	0.0549 (19)	0.0017 (13)	0.0029 (14)	0.0049 (15)
C13	0.0419 (17)	0.0336 (16)	0.0430 (18)	−0.0013 (13)	0.0064 (14)	−0.0040 (14)
C14	0.0381 (17)	0.0368 (18)	0.0432 (17)	0.0001 (13)	0.0023 (13)	0.0006 (14)
C15	0.063 (2)	0.045 (2)	0.0504 (19)	−0.0068 (16)	0.0176 (16)	0.0015 (16)
C16	0.062 (4)	0.033 (3)	0.060 (3)	0.001 (3)	0.017 (3)	0.007 (2)
C17	0.059 (4)	0.046 (3)	0.057 (3)	−0.012 (3)	0.002 (3)	−0.009 (2)
C16'	0.062 (4)	0.033 (3)	0.060 (3)	0.001 (3)	0.017 (3)	0.007 (2)
C17'	0.059 (4)	0.046 (3)	0.057 (3)	−0.012 (3)	0.002 (3)	−0.009 (2)
C18	0.081 (2)	0.0390 (19)	0.054 (2)	−0.0103 (17)	0.0197 (18)	−0.0048 (16)

Geometric parameters (Å, º) top

Cu1—Cl1	2.102 (3)	C9—H9	0.9300
Cu1—N1	1.928 (4)	C10—H10	0.9300
Cu1—N2	2.236 (4)	C11—C12	1.458 (4)
Cu1'—Cl1	2.112 (6)	C13—C14	1.431 (4)
Cu1'—N1	2.268 (7)	C13—C18	1.501 (4)
Cu1'—N2	1.858 (6)	C14—C15	1.504 (4)
N1—C1	1.339 (4)	C15—C16'	1.526 (7)
N1—C12	1.362 (4)	C15—C16	1.530 (5)
N2—C10	1.329 (4)	C15—H15A	0.9700
N2—C11	1.353 (4)	C15—H15B	0.9700
N3—C13	1.316 (4)	C15—H15C	0.9700
N3—C5	1.358 (3)	C15—H15D	0.9700
N4—C14	1.325 (3)	C16—C17	1.538 (6)
N4—C6	1.356 (4)	C16—H16A	0.9700
C1—C2	1.393 (4)	C16—H16B	0.9700
C1—H1	0.9300	C17—C18	1.528 (5)
C2—C3	1.361 (4)	C17—H17A	0.9700
C2—H2	0.9300	C17—H17B	0.9700
C3—C4	1.404 (4)	C16'—C17'	1.515 (8)
C3—H3	0.9300	C16'—H16C	0.9700
C4—C12	1.395 (4)	C16'—H16D	0.9700
C4—C5	1.457 (4)	C17'—C18	1.492 (7)
C5—C6	1.399 (4)	C17'—H17C	0.9700
C6—C7	1.453 (4)	C17'—H17D	0.9700
C7—C11	1.402 (4)	C18—H18A	0.9700
C7—C8	1.411 (4)	C18—H18B	0.9700
C8—C9	1.374 (4)	C18—H18C	0.9700
C8—H8	0.9300	C18—H18D	0.9700
C9—C10	1.394 (5)

N1—Cu1—Cl1	155.21 (19)	N3—C13—C14	121.6 (2)
N1—Cu1—N2	80.06 (15)	N3—C13—C18	118.4 (3)
Cl1—Cu1—N2	124.71 (15)	C14—C13—C18	120.0 (2)
N2—Cu1'—Cl1	150.9 (4)	N4—C14—C13	120.8 (2)
N2—Cu1'—N1	80.7 (2)	N4—C14—C15	117.1 (3)
Cl1—Cu1'—N1	127.9 (3)	C13—C14—C15	122.1 (2)
C1—N1—C12	117.2 (3)	C14—C15—C16'	112.9 (4)
C1—N1—Cu1	124.7 (2)	C14—C15—C16	114.5 (3)
C12—N1—Cu1	118.1 (2)	C14—C15—H15A	108.6
C1—N1—Cu1'	136.7 (3)	C16—C15—H15A	108.6
C12—N1—Cu1'	106.1 (2)	C14—C15—H15B	108.6
C10—N2—C11	117.8 (3)	C16—C15—H15B	108.6
C10—N2—Cu1'	122.8 (3)	H15A—C15—H15B	107.6
C11—N2—Cu1'	119.3 (3)	C14—C15—H15C	109.0
C10—N2—Cu1	134.2 (2)	C16'—C15—H15C	109.0
C11—N2—Cu1	107.9 (2)	C14—C15—H15D	109.0
C13—N3—C5	117.9 (2)	C16'—C15—H15D	109.0
C14—N4—C6	117.7 (2)	H15C—C15—H15D	107.8
N1—C1—C2	123.2 (3)	C15—C16—C17	109.5 (3)
N1—C1—H1	118.4	C15—C16—H16A	109.8
C2—C1—H1	118.4	C17—C16—H16A	109.8
C3—C2—C1	119.4 (3)	C15—C16—H16B	109.8
C3—C2—H2	120.3	C17—C16—H16B	109.8
C1—C2—H2	120.3	H16A—C16—H16B	108.2
C2—C3—C4	119.4 (3)	C18—C17—C16	109.2 (4)
C2—C3—H3	120.3	C18—C17—H17A	109.8
C4—C3—H3	120.3	C16—C17—H17A	109.8
C12—C4—C3	117.8 (3)	C18—C17—H17B	109.8
C12—C4—C5	119.5 (3)	C16—C17—H17B	109.8
C3—C4—C5	122.7 (3)	H17A—C17—H17B	108.3
N3—C5—C6	120.7 (3)	C17'—C16'—C15	111.4 (6)
N3—C5—C4	119.0 (3)	C17'—C16'—H16C	109.3
C6—C5—C4	120.3 (3)	C15—C16'—H16C	109.3
N4—C6—C5	121.4 (3)	C17'—C16'—H16D	109.3
N4—C6—C7	118.6 (3)	C15—C16'—H16D	109.3
C5—C6—C7	120.0 (3)	H16C—C16'—H16D	108.0
C11—C7—C8	117.5 (3)	C18—C17'—C16'	113.4 (6)
C11—C7—C6	120.0 (3)	C18—C17'—H17C	108.9
C8—C7—C6	122.5 (3)	C16'—C17'—H17C	108.9
C9—C8—C7	119.4 (3)	C18—C17'—H17D	108.9
C9—C8—H8	120.3	C16'—C17'—H17D	108.9
C7—C8—H8	120.3	H17C—C17'—H17D	107.7
C8—C9—C10	118.7 (3)	C17'—C18—C13	116.0 (4)
C8—C9—H9	120.6	C13—C18—C17	112.4 (3)
C10—C9—H9	120.6	C13—C18—H18A	109.1
N2—C10—C9	123.6 (3)	C17—C18—H18A	109.1
N2—C10—H10	118.2	C13—C18—H18B	109.1
C9—C10—H10	118.2	C17—C18—H18B	109.1
N2—C11—C7	122.9 (3)	H18A—C18—H18B	107.9
N2—C11—C12	117.4 (3)	C17'—C18—H18C	108.3
C7—C11—C12	119.7 (3)	C13—C18—H18C	108.3
N1—C12—C4	123.0 (3)	C17'—C18—H18D	108.3
N1—C12—C11	116.5 (3)	C13—C18—H18D	108.3
C4—C12—C11	120.5 (3)	H18C—C18—H18D	107.4

N1—Cu1—Cl1—Cu1'	175.5 (12)	C7—C8—C9—C10	0.3 (5)
N2—Cu1—Cl1—Cu1'	−6.9 (7)	C11—N2—C10—C9	1.7 (5)
N2—Cu1'—Cl1—Cu1	165.8 (15)	Cu1'—N2—C10—C9	−177.9 (3)
N1—Cu1'—Cl1—Cu1	−2.1 (6)	Cu1—N2—C10—C9	−175.5 (3)
Cl1—Cu1—N1—C1	−3.3 (6)	C8—C9—C10—N2	−1.9 (5)
N2—Cu1—N1—C1	178.7 (3)	C10—N2—C11—C7	0.2 (4)
Cl1—Cu1—N1—C12	176.5 (3)	Cu1'—N2—C11—C7	179.8 (3)
N2—Cu1—N1—C12	−1.5 (2)	Cu1—N2—C11—C7	178.1 (2)
Cl1—Cu1—N1—Cu1'	−174.7 (14)	C10—N2—C11—C12	−179.7 (3)
N2—Cu1—N1—Cu1'	7.3 (10)	Cu1'—N2—C11—C12	−0.1 (4)
N2—Cu1'—N1—C1	178.5 (3)	Cu1—N2—C11—C12	−1.8 (3)
Cl1—Cu1'—N1—C1	−7.5 (6)	C8—C7—C11—N2	−1.7 (4)
N2—Cu1'—N1—C12	0.7 (3)	C6—C7—C11—N2	178.1 (3)
Cl1—Cu1'—N1—C12	174.7 (3)	C8—C7—C11—C12	178.2 (3)
N2—Cu1'—N1—Cu1	−171.3 (12)	C6—C7—C11—C12	−2.0 (4)
Cl1—Cu1'—N1—Cu1	2.8 (8)	C1—N1—C12—C4	−0.8 (4)
Cl1—Cu1'—N2—C10	9.0 (8)	Cu1—N1—C12—C4	179.4 (2)
N1—Cu1'—N2—C10	179.3 (3)	Cu1'—N1—C12—C4	177.5 (3)
Cl1—Cu1'—N2—C11	−170.6 (6)	C1—N1—C12—C11	−179.2 (3)
N1—Cu1'—N2—C11	−0.3 (3)	Cu1—N1—C12—C11	1.0 (4)
Cl1—Cu1'—N2—Cu1	−162.4 (18)	Cu1'—N1—C12—C11	−0.9 (3)
N1—Cu1'—N2—Cu1	7.9 (11)	C3—C4—C12—N1	0.4 (4)
N1—Cu1—N2—C10	179.2 (3)	C5—C4—C12—N1	180.0 (3)
Cl1—Cu1—N2—C10	0.2 (4)	C3—C4—C12—C11	178.8 (3)
N1—Cu1—N2—C11	1.8 (2)	C5—C4—C12—C11	−1.6 (4)
Cl1—Cu1—N2—C11	−177.18 (19)	N2—C11—C12—N1	0.8 (4)
N1—Cu1—N2—Cu1'	−170.7 (13)	C7—C11—C12—N1	−179.1 (3)
Cl1—Cu1—N2—Cu1'	10.3 (11)	N2—C11—C12—C4	−177.7 (3)
C12—N1—C1—C2	0.6 (5)	C7—C11—C12—C4	2.4 (4)
Cu1—N1—C1—C2	−179.6 (3)	C5—N3—C13—C14	0.8 (4)
Cu1'—N1—C1—C2	−177.0 (3)	C5—N3—C13—C18	−178.1 (3)
N1—C1—C2—C3	−0.1 (5)	C6—N4—C14—C13	1.3 (4)
C1—C2—C3—C4	−0.3 (5)	C6—N4—C14—C15	179.7 (3)
C2—C3—C4—C12	0.1 (4)	N3—C13—C14—N4	−1.4 (4)
C2—C3—C4—C5	−179.4 (3)	C18—C13—C14—N4	177.5 (3)
C13—N3—C5—C6	−0.2 (4)	N3—C13—C14—C15	−179.7 (3)
C13—N3—C5—C4	178.3 (3)	C18—C13—C14—C15	−0.8 (4)
C12—C4—C5—N3	−178.1 (3)	N4—C14—C15—C16'	−159.2 (5)
C3—C4—C5—N3	1.5 (4)	C13—C14—C15—C16'	19.2 (6)
C12—C4—C5—C6	0.5 (4)	N4—C14—C15—C16	172.1 (3)
C3—C4—C5—C6	−180.0 (3)	C13—C14—C15—C16	−9.5 (5)
C14—N4—C6—C5	−0.7 (4)	C14—C15—C16—C17	41.6 (5)
C14—N4—C6—C7	−179.1 (2)	C15—C16—C17—C18	−64.6 (5)
N3—C5—C6—N4	0.1 (4)	C14—C15—C16'—C17'	−46.3 (9)
C4—C5—C6—N4	−178.4 (2)	C16—C15—C16'—C17'	53.0 (8)
N3—C5—C6—C7	178.5 (2)	C15—C16'—C17'—C18	57.2 (11)
C4—C5—C6—C7	0.0 (4)	C16'—C17'—C18—C13	−38.7 (10)
N4—C6—C7—C11	179.2 (2)	C16'—C17'—C18—C17	51.3 (7)
C5—C6—C7—C11	0.8 (4)	N3—C13—C18—C17'	−170.6 (5)
N4—C6—C7—C8	−1.0 (4)	C14—C13—C18—C17'	10.4 (7)
C5—C6—C7—C8	−179.4 (3)	N3—C13—C18—C17	156.8 (3)
C11—C7—C8—C9	1.4 (4)	C14—C13—C18—C17	−22.1 (5)
C6—C7—C8—C9	−178.4 (3)	C16—C17—C18—C13	54.5 (5)

Experimental details

Crystal data
Chemical formula	[CuCl(C₁₈H₁₄N₄)]
M_r	385.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.9405 (10), 15.8861 (19), 12.6312 (16)
β (°)	99.531 (2)
V (Å³)	1571.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.57
Crystal size (mm)	0.15 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.799, 0.859
No. of measured, independent and observed [I > 2σ(I)] reflections	8464, 3064, 1957
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.119, 0.99
No. of reflections	3064
No. of parameters	233
No. of restraints	16
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.34

Computer programs: APEX (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cu1—Cl1	2.102 (3)	Cu1'—Cl1	2.112 (6)
Cu1—N1	1.928 (4)	Cu1'—N1	2.268 (7)
Cu1—N2	2.236 (4)	Cu1'—N2	1.858 (6)

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2002). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Che, G.-B., Li, W.-L., Kong, Z.-G., Su, Z.-S., Chu, B., Li, B., Zhang, Z.-Q., Hu, Z.-Z. & Chi, H.-J. (2006). Synth. Commun. 36, 2519–2524. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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