μ-Chlorido-bis­({N-benzyl-N′-[2-(benzyl­amino)eth­yl]ethane-1,2-diamine}chloridocopper(II)) chloride

In the title compound, [Cu₂Cl₃(C₁₈H₂₅N₃)₂]Cl, the asymmetric unit consists of one half of a μ-chlorido-bis­[{N-benzyl-N′-[2-(benzyl­amino)eth­yl]ethane-1,2-diamine}chloridocopper(II)] complex cation and one chloride anion lying on a twofold rotation axis. The two Cu^II centres are symmetry-related by a twofold rotation axis passing through the bridging Cl atom. The Cu atoms exhibit a distorted square-pyramidal coordination environment. The basal and apical Cu—Cl bond lengths are 2.254 (2) and 2.658 (2) Å, respectively. The Cu...Cu distance and Cu—Cl—Cu angle are 4.349 (6) Å and 109.8 (2)°, respectively. In the crystal structure, the mol­ecules of the complex are linked into chains along b and a by C—H...π hydrogen bonds. The chloride anion links these chains along c into a three-dimensional network structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.015 Å
• R factor = 0.056
• wR factor = 0.103
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.27
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   Cl2     ..       5.74 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C13    -C18           1.36 Ang.
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         15
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2     ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3     ...          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               3398
           Count of symmetry unique reflns         1927
           Completeness (_total/calc)            176.34%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1471
           Fraction of Friedel pairs measured     0.763
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of N1     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of N3     = .          S
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       2.09
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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

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S1. Comment

Dinuclear copper(II) complexes, especially those containing a chlorine bridging ligand, have been the subject of extensive reseach because of their magnetic exchange interactions between ligand-bridged copper atoms, which mimic the biological active site in copper proteins (Lee et al., 2005; Rapheal et al., 2007). In the classical case, the copper atom is five coordinate and bridged by a monochlorine atom or eventually two chlorine atoms, depending on the coordination environment. Here, we report the synthesis and crystal structure of a new monochlorine bridged dicopper(II) complex, [Cu₂ Cl₃ (C₁₈ H₂₅ N₃)₂]⁺.Cl^- (I).

In complex (I), the copper atom is five coordinated by one tridentate chelating (N-benzyl-N'-[2-(benzylamino)ethyl)]ethane-1,2-diamine) ligand and two chloride atoms, to form a distorted square pyramid geometry (Fig. 1). Three N atoms of the ligand and a monodentate chlorine are at the basal square plane, while the bridging chlorine atom is at the apical position. The Cu1 atom is shifted by 0.202 (3)Å from the basal plane towards the apical site. The dihedral angles between the basal plane and the C6—C11 (Cg1) and C13—C18 (Cg2) phenyl rings are 48.9 (3)° and 62.1 (3)°, respectively. Coordination distances are shown in Table 1. The Cu···Cu separation is 4.349 (6) Å, and the Cu—Cl—Cu angle is 109.8 (2)°.

In the crystal structure, C—H···π hydrogen bonds link the molecules into two types of chains running along b and a respectively (Fig. 2 and 3, Table 2). The chloride anion,, which also resides on a two fold axis, in turn, link these chains along the c direction (Fig. 4, Table 2), into a three-dimensinal network structure.

Related literature

For related literature, see: Lee et al. (2005); Rapheal et al. (2007).

S2. Experimental

N¹-benzyl-N²-(2-(benzylamino)ethyl)ethane-1,2-diamine (4 mmol) was dissolved in ethanol (20 ml), and an aqueous solution (10 ml) of cupric chloride (2 mmol) was added. The reaction mixture was stirred 4 h at 323–333k. The solution was then cooled slowly to room temperature and filtered. Blue crystals suitable for X-ray diffraction were obtained by evaporation of an ethanol solution.

S3. Refinement

The space group was uniquely assigned from the systematic absences. All H atoms were located in difference Fourier maps. H atoms bonded to C and N atoms were treated as riding atoms, with C—H distances of 0.93 Å (aryl), 0.97 Å(methylene) and N—H distances of 0.91 Å (amine), and with U_iso(H) = 1.2U_eq(C,N) (aryl, methylene, amine).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids drawn at a 30% probability level. Unlabelled atoms in the cation are related to labelled ones by (-x, y, -z).
	Fig. 2. A partial packing view of (I), showing the formation of a hydrogen-bonded chain along b, built from C—H···Cg1(π) interactions, Cg1: C6—C11. For clarity, H atomes not involved in hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds. [symmetry code: (A) - x, y, - z, (B) x, -1 + y, z, (C) x, 1 + y, - z, (D) - x, - 1 + y, - z, (E) - x, 1 + y, -z].
	Fig. 3. A partial packing view of (I), showing the formation of a hydrogen-bonded chain along a, built from C—H···Cg1(π) interactions, Cg1: C6—C11. For clarity, H atoms not involved in hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds. [symmetry code: (A) - x, y, - z, (I) 1/2 - x, -1/2 + y, - z, (J) 1 - x, -1 + y, - z].
	Fig. 4. A partial packing view of (I), showing the C—H···Cl interaction linking the above referenced chains along c. For clarity, H atomes not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds. [symmetry code: (A) - x, y, - z, (F) x, y, 1 + z, (G) x, y, - 1 + z, (H) - x, y, 1 - z].

µ-Chlorido-bis({N-benzyl-N'-[2-(benzylamino)ethyl]ethane- 1,2-diamine}chloridocopper(II))

Crystal data

[Cu2Cl3(C18H25N3)2]Cl	F(000) = 868
Mr = 835.70	Dx = 1.376 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 896 reflections
a = 25.584 (3) Å	θ = 2.9–25.3°
b = 7.4506 (11) Å	µ = 1.35 mm^−1
c = 11.5739 (15) Å	T = 298 K
β = 113.926 (2)°	Block, blue
V = 2016.6 (5) Å^3	0.27 × 0.14 × 0.11 mm
Z = 2

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	3398 independent reflections
Radiation source: fine-focus sealed tube	1758 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→30
Tmin = 0.712, Tmax = 0.866	k = −8→8
5224 measured reflections	l = −12→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0208P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
3398 reflections	Δρmax = 0.91 e Å^−3
219 parameters	Δρmin = −0.40 e Å^−3
1 restraint	Absolute structure: Flack (1983), 1474 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (3)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	−0.00397 (4)	0.58358 (18)	0.18416 (10)	0.0507 (3)
Cl1	−0.06597 (8)	0.8020 (3)	0.0790 (2)	0.0635 (7)
Cl2	0.0000	0.3784 (4)	0.0000	0.0528 (9)
Cl3	0.0000	0.7398 (8)	0.5000	0.176 (3)
N1	0.0678 (2)	0.7293 (9)	0.2071 (6)	0.0408 (18)
H1	0.0658	0.7572	0.1288	0.049*
N2	0.0526 (3)	0.4103 (10)	0.3005 (6)	0.054 (2)
H2	0.0581	0.3252	0.2501	0.065*
N3	−0.0622 (3)	0.4348 (10)	0.2208 (7)	0.056 (2)
H3	−0.0721	0.5016	0.2746	0.067*
C1	0.1169 (3)	0.6147 (12)	0.2676 (8)	0.047 (2)
H1A	0.1509	0.6873	0.3088	0.057*
H1B	0.1225	0.5401	0.2048	0.057*
C2	0.1072 (3)	0.4948 (11)	0.3664 (8)	0.056 (3)
H2A	0.1372	0.4053	0.3995	0.067*
H2B	0.1070	0.5667	0.4360	0.067*
C3	0.0265 (4)	0.3159 (13)	0.3769 (8)	0.060 (3)
H3A	0.0276	0.3921	0.4457	0.072*
H3B	0.0476	0.2069	0.4125	0.072*
C4	−0.0348 (4)	0.2709 (13)	0.2912 (9)	0.062 (3)
H4A	−0.0357	0.1764	0.2327	0.074*
H4B	−0.0551	0.2293	0.3411	0.074*
C5	0.0710 (3)	0.8999 (12)	0.2756 (8)	0.057 (3)
H5A	0.0680	0.8734	0.3547	0.068*
H5B	0.0386	0.9743	0.2256	0.068*
C6	0.1253 (3)	1.0044 (10)	0.3033 (9)	0.048 (2)
C7	0.1353 (3)	1.0868 (16)	0.2091 (8)	0.060 (2)
H7	0.1076	1.0810	0.1268	0.071*
C8	0.1848 (4)	1.1774 (12)	0.2322 (11)	0.070 (3)
H8	0.1906	1.2312	0.1658	0.084*
C9	0.2256 (4)	1.1893 (13)	0.3517 (13)	0.080 (4)
H9	0.2598	1.2489	0.3671	0.097*
C10	0.2165 (4)	1.1132 (16)	0.4498 (10)	0.082 (3)
H10	0.2443	1.1231	0.5319	0.098*
C11	0.1657 (4)	1.0207 (11)	0.4267 (9)	0.066 (3)
H11	0.1591	0.9707	0.4932	0.079*
C12	−0.1162 (3)	0.3945 (14)	0.1112 (8)	0.071 (3)
H12A	−0.1071	0.3243	0.0511	0.086*
H12B	−0.1327	0.5068	0.0703	0.086*
C13	−0.1609 (3)	0.2938 (14)	0.1405 (9)	0.059 (3)
C14	−0.1898 (4)	0.3716 (15)	0.2039 (10)	0.088 (3)
H14	−0.1802	0.4871	0.2360	0.105*
C15	−0.2333 (5)	0.2800 (17)	0.2209 (11)	0.100 (4)
H15	−0.2541	0.3371	0.2601	0.120*
C16	−0.2455 (4)	0.1112 (19)	0.1818 (11)	0.094 (4)
H16	−0.2737	0.0490	0.1965	0.113*
C17	−0.2171 (4)	0.0308 (14)	0.1209 (11)	0.096 (4)
H17	−0.2265	−0.0860	0.0914	0.116*
C18	−0.1744 (4)	0.1184 (18)	0.1018 (10)	0.082 (4)
H18	−0.1542	0.0591	0.0622	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0451 (5)	0.0497 (6)	0.0583 (7)	−0.0005 (7)	0.0218 (5)	0.0036 (8)
Cl1	0.0548 (15)	0.0638 (18)	0.0719 (18)	0.0134 (12)	0.0258 (14)	0.0096 (14)
Cl2	0.064 (2)	0.052 (2)	0.044 (2)	0.000	0.0224 (17)	0.000
Cl3	0.255 (7)	0.139 (6)	0.203 (7)	0.000	0.166 (6)	0.000
N1	0.040 (4)	0.046 (5)	0.037 (5)	0.002 (3)	0.016 (4)	0.004 (4)
N2	0.054 (5)	0.062 (5)	0.044 (5)	0.006 (4)	0.018 (4)	−0.013 (4)
N3	0.047 (5)	0.065 (6)	0.055 (5)	−0.002 (4)	0.020 (4)	−0.010 (4)
C1	0.029 (4)	0.034 (6)	0.075 (6)	0.000 (4)	0.017 (4)	0.000 (5)
C2	0.055 (6)	0.053 (6)	0.052 (6)	0.005 (5)	0.012 (5)	0.000 (5)
C3	0.074 (7)	0.058 (7)	0.049 (6)	−0.004 (5)	0.028 (6)	−0.007 (5)
C4	0.078 (7)	0.050 (7)	0.067 (7)	0.002 (5)	0.039 (6)	−0.002 (6)
C5	0.062 (6)	0.052 (7)	0.062 (7)	0.009 (5)	0.031 (5)	0.006 (6)
C6	0.037 (5)	0.036 (6)	0.058 (7)	0.002 (4)	0.005 (5)	−0.004 (5)
C7	0.059 (6)	0.051 (6)	0.054 (6)	−0.005 (8)	0.009 (5)	−0.004 (7)
C8	0.078 (8)	0.056 (7)	0.074 (8)	−0.023 (6)	0.027 (7)	−0.018 (6)
C9	0.061 (7)	0.052 (7)	0.123 (11)	−0.026 (5)	0.031 (8)	−0.026 (7)
C10	0.069 (7)	0.051 (9)	0.086 (9)	−0.010 (7)	−0.009 (6)	−0.007 (7)
C11	0.077 (7)	0.053 (8)	0.054 (7)	0.005 (5)	0.013 (7)	0.000 (5)
C12	0.059 (6)	0.097 (9)	0.053 (7)	−0.016 (6)	0.018 (6)	0.002 (6)
C13	0.046 (6)	0.057 (7)	0.081 (8)	0.001 (5)	0.032 (6)	0.004 (6)
C14	0.092 (8)	0.069 (8)	0.133 (10)	0.000 (6)	0.076 (8)	−0.008 (7)
C15	0.107 (9)	0.085 (10)	0.158 (12)	0.016 (8)	0.105 (9)	0.008 (9)
C16	0.085 (7)	0.066 (10)	0.155 (11)	−0.006 (8)	0.072 (7)	0.012 (10)
C17	0.093 (9)	0.058 (10)	0.154 (12)	−0.013 (6)	0.067 (9)	−0.011 (7)
C18	0.066 (7)	0.089 (11)	0.102 (8)	0.010 (7)	0.045 (6)	0.010 (9)

Geometric parameters (Å, º)

Cu1—N2	1.999 (7)	C5—H5A	0.9700
Cu1—N3	2.035 (6)	C5—H5B	0.9700
Cu1—N1	2.055 (6)	C6—C7	1.363 (11)
Cu1—Cl1	2.254 (2)	C6—C11	1.388 (10)
Cu1—Cl2	2.658 (2)	C7—C8	1.363 (11)
Cu1—Cl3	3.798 (2)	C7—H7	0.9300
Cl2—Cu1^i	2.658 (2)	C8—C9	1.357 (13)
N1—C1	1.444 (9)	C8—H8	0.9300
N1—C5	1.482 (9)	C9—C10	1.370 (13)
N1—H1	0.9100	C9—H9	0.9300
N2—C2	1.437 (8)	C10—C11	1.398 (11)
N2—C3	1.483 (9)	C10—H10	0.9300
N2—H2	0.9100	C11—H11	0.9300
N3—C4	1.478 (10)	C12—C13	1.518 (10)
N3—C12	1.478 (8)	C12—H12A	0.9700
N3—H3	0.9100	C12—H12B	0.9700
C1—C2	1.547 (10)	C13—C14	1.364 (11)
C1—H1A	0.9700	C13—C18	1.379 (15)
C1—H1B	0.9700	C14—C15	1.386 (12)
C2—H2A	0.9700	C14—H14	0.9300
C2—H2B	0.9700	C15—C16	1.331 (15)
C3—C4	1.515 (9)	C15—H15	0.9300
C3—H3A	0.9700	C16—C17	1.342 (13)
C3—H3B	0.9700	C16—H16	0.9300
C4—H4A	0.9700	C17—C18	1.365 (12)
C4—H4B	0.9700	C17—H17	0.9300
C5—C6	1.508 (10)	C18—H18	0.9300
N2—Cu1—N3	84.2 (3)	N3—C4—H4A	110.1
N2—Cu1—N1	83.6 (3)	C3—C4—H4A	110.1
N3—Cu1—N1	162.2 (3)	N3—C4—H4B	110.1
N2—Cu1—Cl1	171.5 (2)	C3—C4—H4B	110.1
N3—Cu1—Cl1	95.2 (2)	H4A—C4—H4B	108.4
N1—Cu1—Cl1	94.85 (19)	N1—C5—C6	113.8 (7)
N2—Cu1—Cl2	85.18 (19)	N1—C5—H5A	108.8
N3—Cu1—Cl2	97.1 (2)	C6—C5—H5A	108.8
N1—Cu1—Cl2	94.85 (19)	N1—C5—H5B	108.8
Cl1—Cu1—Cl2	103.26 (9)	C6—C5—H5B	108.8
N2—Cu1—Cl3	79.64 (19)	H5A—C5—H5B	107.7
N3—Cu1—Cl3	72.7 (2)	C7—C6—C11	118.7 (8)
N1—Cu1—Cl3	92.3 (2)	C7—C6—C5	121.2 (8)
Cl1—Cu1—Cl3	92.12 (10)	C11—C6—C5	120.2 (9)
Cl2—Cu1—Cl3	162.39 (11)	C8—C7—C6	121.8 (8)
Cu1—Cl2—Cu1^i	109.79 (12)	C8—C7—H7	119.1
C1—N1—C5	113.5 (6)	C6—C7—H7	119.1
C1—N1—Cu1	107.8 (5)	C9—C8—C7	120.1 (10)
C5—N1—Cu1	112.0 (5)	C9—C8—H8	119.9
C1—N1—H1	107.8	C7—C8—H8	119.9
C5—N1—H1	107.8	C8—C9—C10	119.9 (10)
Cu1—N1—H1	107.8	C8—C9—H9	120.1
C2—N2—C3	117.9 (7)	C10—C9—H9	120.1
C2—N2—Cu1	110.9 (6)	C9—C10—C11	120.2 (9)
C3—N2—Cu1	109.3 (5)	C9—C10—H10	119.9
C2—N2—H2	106.0	C11—C10—H10	119.9
C3—N2—H2	106.0	C6—C11—C10	119.2 (9)
Cu1—N2—H2	106.0	C6—C11—H11	120.4
C4—N3—C12	112.0 (7)	C10—C11—H11	120.4
C4—N3—Cu1	109.9 (5)	N3—C12—C13	115.8 (7)
C12—N3—Cu1	116.0 (5)	N3—C12—H12A	108.3
C4—N3—H3	106.0	C13—C12—H12A	108.3
C12—N3—H3	106.0	N3—C12—H12B	108.3
Cu1—N3—H3	106.0	C13—C12—H12B	108.3
N1—C1—C2	109.4 (6)	H12A—C12—H12B	107.4
N1—C1—H1A	109.8	C14—C13—C18	117.3 (9)
C2—C1—H1A	109.8	C14—C13—C12	122.2 (10)
N1—C1—H1B	109.8	C18—C13—C12	120.5 (9)
C2—C1—H1B	109.8	C13—C14—C15	120.6 (10)
H1A—C1—H1B	108.2	C13—C14—H14	119.7
N2—C2—C1	105.9 (7)	C15—C14—H14	119.7
N2—C2—H2A	110.6	C16—C15—C14	120.6 (11)
C1—C2—H2A	110.6	C16—C15—H15	119.7
N2—C2—H2B	110.6	C14—C15—H15	119.7
C1—C2—H2B	110.6	C15—C16—C17	119.9 (11)
H2A—C2—H2B	108.7	C15—C16—H16	120.1
N2—C3—C4	108.2 (7)	C17—C16—H16	120.1
N2—C3—H3A	110.1	C16—C17—C18	120.8 (12)
C4—C3—H3A	110.1	C16—C17—H17	119.6
N2—C3—H3B	110.1	C18—C17—H17	119.6
C4—C3—H3B	110.1	C17—C18—C13	120.8 (10)
H3A—C3—H3B	108.4	C17—C18—H18	119.6
N3—C4—C3	108.2 (8)	C13—C18—H18	119.6
N2—Cu1—Cl2—Cu1^i	−137.1 (2)	Cu1—N1—C1—C2	−37.5 (8)
N3—Cu1—Cl2—Cu1^i	139.3 (2)	C3—N2—C2—C1	−167.9 (7)
N1—Cu1—Cl2—Cu1^i	−53.97 (18)	Cu1—N2—C2—C1	−40.9 (7)
Cl1—Cu1—Cl2—Cu1^i	42.18 (6)	N1—C1—C2—N2	52.2 (8)
Cl3—Cu1—Cl2—Cu1^i	−167.59 (13)	C2—N2—C3—C4	168.9 (7)
N2—Cu1—N1—C1	12.1 (5)	Cu1—N2—C3—C4	41.1 (8)
N3—Cu1—N1—C1	59.5 (12)	C12—N3—C4—C3	164.4 (6)
Cl1—Cu1—N1—C1	−176.2 (5)	Cu1—N3—C4—C3	33.8 (8)
Cl2—Cu1—N1—C1	−72.5 (5)	N2—C3—C4—N3	−49.2 (9)
Cl3—Cu1—N1—C1	91.4 (5)	C1—N1—C5—C6	53.1 (10)
N2—Cu1—N1—C5	−113.5 (5)	Cu1—N1—C5—C6	175.6 (6)
N3—Cu1—N1—C5	−66.1 (11)	N1—C5—C6—C7	70.4 (11)
Cl1—Cu1—N1—C5	58.2 (5)	N1—C5—C6—C11	−110.6 (8)
Cl2—Cu1—N1—C5	161.9 (5)	C11—C6—C7—C8	2.9 (14)
Cl3—Cu1—N1—C5	−34.2 (5)	C5—C6—C7—C8	−178.1 (8)
N3—Cu1—N2—C2	−149.5 (6)	C6—C7—C8—C9	−0.7 (15)
N1—Cu1—N2—C2	17.4 (5)	C7—C8—C9—C10	−1.4 (15)
Cl2—Cu1—N2—C2	112.9 (5)	C8—C9—C10—C11	1.1 (16)
Cl3—Cu1—N2—C2	−76.1 (5)	C7—C6—C11—C10	−3.1 (12)
N3—Cu1—N2—C3	−17.9 (5)	C5—C6—C11—C10	177.9 (8)
N1—Cu1—N2—C3	149.0 (5)	C9—C10—C11—C6	1.1 (15)
Cl2—Cu1—N2—C3	−115.6 (5)	C4—N3—C12—C13	56.4 (10)
Cl3—Cu1—N2—C3	55.5 (5)	Cu1—N3—C12—C13	−176.2 (7)
N2—Cu1—N3—C4	−9.3 (6)	N3—C12—C13—C14	70.1 (12)
N1—Cu1—N3—C4	−56.5 (12)	N3—C12—C13—C18	−110.7 (11)
Cl1—Cu1—N3—C4	179.2 (5)	C18—C13—C14—C15	−4.0 (16)
Cl2—Cu1—N3—C4	75.1 (6)	C12—C13—C14—C15	175.3 (9)
Cl3—Cu1—N3—C4	−90.2 (5)	C13—C14—C15—C16	3.7 (18)
N2—Cu1—N3—C12	−137.6 (6)	C14—C15—C16—C17	−2.6 (19)
N1—Cu1—N3—C12	175.1 (8)	C15—C16—C17—C18	1.9 (19)
Cl1—Cu1—N3—C12	50.9 (6)	C16—C17—C18—C13	−2.4 (17)
Cl2—Cu1—N3—C12	−53.2 (6)	C14—C13—C18—C17	3.4 (16)
Cl3—Cu1—N3—C12	141.5 (6)	C12—C13—C18—C17	−175.9 (9)
C5—N1—C1—C2	87.2 (8)

Symmetry code: (i) −x, y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cl3	0.97	2.82	3.640 (11)	143
C2—H2A···Cg1^ii	0.97	2.74	3.547 (9)	141
C15—H15···Cg1^iii	0.93	2.97	3.872 (14)	163

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