Chloro­bis­(clemizole)copper(II) chloride ethanol solvate

The structure of chloro­bis{[1-(p-chloro­phenyl­methyl)-2-(1-pyrrolidin-1-yl­methyl)-2,3-di­hydro-1H-benz­imidazole-N²,N³]}copper(II) chloride ethanol solvate, [CuCl(C₁₉H₂₀ClN₃)₂]Cl·C₂H₆O, contains two mol­ecules of clemizole bound in a bidentate manner to copper, with significantly different Cu-N distances; the pyrrolidinyl N-Cu and imidazole N-Cu distances are 1.959 (4) and 2.366 (5) Å for ligand 1, and 1.976 (4) and 2.193 (4) Å for ligand 2, respectively. The geometry around copper is distorted trigonal bipyramidal, with a Cu-Cl distance of 2.2699 (15) Å.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• Disorder in solvent or counterion
• R factor = 0.051
• wR factor = 0.142
• Data-to-parameter ratio = 8.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_302  Alert C Anion/Solvent disorder .......................      43.00 Perc.

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #      1
                   N1A -CU1 -N1  -C7    -70.40  1.60   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #      5
                   N1A -CU1 -N1  -C1    115.30  1.40   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     76
                   N1  -CU1 -N1A -C7A    -1.20  1.70   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     80
                   N1  -CU1 -N1A -C1A   173.10  1.30   1.555   1.555   1.555   1.555

General Notes



FORMU_01  There is a discrepancy between the atom counts in the
          _chemical_formula_sum and _chemical_formula_moiety. This is
          usually due to the moiety formula being in the wrong format.
          Atom count from _chemical_formula_sum:   C40 H46 Cl4 Cu1 N6 O1
          Atom count from _chemical_formula_moiety:C40 H46 Cl3 Cu2 N6 O1

ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      0.758
          Tmax scaled      0.266 Tmin scaled      0.227

REFLT_03
         From the CIF: _diffrn_reflns_theta_max           68.00
         From the CIF: _reflns_number_total               4073
         Count of symmetry unique reflns         3905
         Completeness (_total/calc)            104.30%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured       168
         Fraction of Friedel pairs measured     0.043
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 5 Alert Level C = Please check

---

S1. Comment

The crystal structures of clemizole hydrochloride (Parvez, 1996), clemizoledichlorozinc(II) (Parvez & Sabir, 1996a) clemizoledichlorocobalt(II), (Parvez & Braitenbach, 2000), clemizole as a free base (Parvez & Sabir, 1996b), clemizole tetrachlorocuprate(II) and clemizole tetrachlorocobaltate(II) (Parvez & Sabir, 1997) have been reported from our laboratory. This H₁ antihistamine has now been incorporated into a copper complex to investigate further the effects such complex formation may have on the conformation of the clemizole moiety. In this paper, we report the structure of bis(clemizole)chlorocopper(II) chloride ethanol solvate, (I).

Fig. 1 shows an ORTEPII (Johnson, 1976) drawing of the cation bis(clemizole)chlorocopper(II) wherein two molecules of clemizole are coordinated in a bidentate mode to copper via pyrrolidinyl and imidazole N atoms with significantly different Cu—N distances of 1.959 (4) and 2.366 (5) Å for ligand 1, and 1.976 (4) and 2.193 (4) Å for ligand 2, respectively; the imidizole nitrogen atom, N3, of ligand 1 has an unusually long bond to copper. The Cu atom is also bound to Cl2, with a distance of 2.2699 (15) Å. The geometry around copper is distorted trigonal bipyramidal with an almost linear N1—Cu1—N1A angle, 172.84 (18)°. Similar distances and geometry have been reported for a number of closely related copper complexes, e.g. chloro(2,5,8,11-tetraethyl-1,2,7,10-tetraazacyclododecane)copper(II) chloride hydrate (Sakurai et al., 1982), chloro(1,4,7,10-tetrabenzyl-2,5,8,11-tetraethyl-1,4,7,10-tetraazacyclo- dodecane)copper(II) chloride (Sakurai et al., 1982), chloro(trans-5,7,12,14-tetramethyl-1,4,8,11-tetra-azacyclotetradecane-6,13- dione dioxime)copper(II) chloride heptahydrate (Bernhardt & Sharpe, 1998), (4,11-dibenzyl-1,4,8,11-tetraazabicyclo[6.6.2]hexadecane)chlorocopper(II) chloride monohydrate (Weisman et al., 1996), and (1,4,8,11-tetra-azabicyclo[6.6.2]hexadecane)chlorocopper(II) chloride trihydrate (Weisman et al., 1996).

The molecular dimensions of the ligands are normal. The important mean bond distances are: Csp2—Cl 1.738 (9), Csp3—Csp3 1.519 (16), Csp3—Csp2 1.506 (5), N—Csp3 1.476 (11), N—Csp2 1.379 (10) and C—C_aromatic 1.382 (18) Å. It is interesting to note that the N1—C7 and N1A—C7A bonds [1.336 (7) and 1.312 (6) Å, respectively] are much shorter than expected for a single bond and that the N2—C7 and N2A—C7A bonds [1.343 (7) and 1.348 (6) Å, respectively] are much longer than expected for a double bond; these bonds must represent a delocalized system with mean N≐C distance of 1.334 (13) Å; the corresponding distances in the structure of clemizoledichlorozinc(II) (Parvez & Sabir, 1996a) were observed to be 1.357 (5) and 1.321 (5) Å, respectively.

The benzimidazole and phenyl rings are essentially planar with maximum deviations of atoms from the least-squares planes being 0.037 (5) and 0.021 (6) Å for ligand 1 and 0.020 (4) and 0.018 (6) Å for ligand 2, respectively. The dihedral angle between the least-squares planes of the benzimidazole and phenyl rings is 81.38 (18)° for ligand 1 and 85.65 (18)° for ligand 2. The corresponding angle in the structures of clemizole dichlorozinc, clemizole hydrochloride, clemizole dichlorocobalt, clemizole as a free base, clemizole tetrachlorocuprate(II) and clemizole tetrachlorocobaltate(II) are 81.1 (4) (Parvez & Sabir, 1996a), 82.8 (9) (Parvez, 1996), 86.2 (2) (Parvez & Braitenbach, 2000), 68.8 (6) (Parvez & Sabir, 1996b), 70.5 (6) and 82.7 (9)° (Parvez & Sabir, 1997), respectively.

An examination of the torsion angle N2—C13—C14—C19 in ligand 1 [-123.4 (7)°] and N2A—C13A—C14A—C19A in ligand 2 [146.7 (6)°] shows that the orientation of the phenyl ring with respect to the imidazole ring in ligand 1 in (I) is somewhat similar to the orientation of these rings in clemizole tetrachlorocobaltate (-116°; Parvez & Sabir, 1997) and the orientation of these rings in ligand 2 in (I) is somewhat similar to the orientation of these rings in clemizole tetrachlorocuprate (133°; Parvez & Sabir, 1997) and clemizole hydrochloride (153°; Parvez, 1996). The pyrrolidinyl rings in each ligand have an N-envelope conformation with N3 0.627 (9) Å out of the plane of the C9—C12 atoms and N3A 0.582 (9) Å out of the plane of the C9A–C12A atoms; similar conformations of the 5-membered ring have been observed in the crystal structures mentioned above.

The structure is composed of independent cations of the complex separated by normal van der Waals distances. The hydrogen bonding interactions exist between Cl^- ions and the ethanol molecules of solvation, both the distances O1H1···Cl3 and O1H1A···Cl3 are 2.73 Å. The benzimidazole moieties of the complex molecules which lie about the inversion centers are stacked parallel to each other.

S2. Experimental

The title compound was synthesized by adding 1.0 mmol of CuCl₂·2H₂0 to 2.0 mmol of clemizole hydrochloride (Sigma Inc.) in 20 ml of ethanol. NH₄OH was added until the pH was 8–9. The solution was evaporated slowly at room temperature and blue prismatic crystals separated after a few days.

S3. Refinement

Based on the systematic absences: h0l, h+l = 2n+1, packing considerations, a statistical analysis of intensity distribution, and the successful solution and refinement of the structure, the space group was determined to be: Pn. The asymmetric unit contains a bis(clemizole)chlorocopper(II) cation, a Cl^- anion and two half molecules of ethanol of solvation. The C and O atoms of the solvent molecules were refined with isotropic displacement parameters while the rest of the non-H atoms were allowed anisotropic vibrations. The partial occupancy factors for the solvents were determined during the initial rounds of calculations and were fixed at 0.50 at the final stages of the refinements. A small degree of disorder was also evident in the solvent molecules, therefore, C—O and C—C distances were constrained. The H atoms were included in the refinements in a riding mode with O—H = 0.82 Å and C—H = 0.93–0.97 Å. The non-methyl and methyl H atoms were allowed isotropic displacement parameters 1.2 and 1.5 times the displacement parameters of the atoms to which they were attached.

Computing details

Data collection: Enraf-Nonius CAD-4 Software. Version 5.0. (Enraf-Nonius, 1989); cell refinement: Enraf-Nonius CAD-4 Software. Version 5.0. (Enraf-Nonius, 1989); data reduction: TEXSAN (Molecular Structure Corporation, 1994); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN (Molecular Structure Corporation, 1994); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

Fig. 1. ORTEPII (Johnson, 1976) drawing of bis(clemizole)chlorocopper(II) with displacement ellipsoids plotted at 30% probability level.

Dichloro[1-(p-chlorophenylmethyl)-2-(1-pyrrolidinylmethyl)benzimidazole- N,N'']copper(II) Ethanol Solvate

Crystal data

[CuCl(C19H20ClN3)2]Cl·C2H6O	F(000) = 866
Mr = 832.17	Dx = 1.293 Mg m^−3
Monoclinic, Pn	Cu Kα radiation, λ = 1.54178 Å
a = 12.809 (3) Å	Cell parameters from 25 reflections
b = 8.608 (2) Å	θ = 15.0–40.0°
c = 19.482 (4) Å	µ = 3.31 mm^−1
β = 95.81 (2)°	T = 293 K
V = 2137.0 (8) Å^3	Prismatic, blue
Z = 2	0.48 × 0.45 × 0.40 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	3871 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.066
Graphite monochromator	θmax = 68.0°, θmin = 5.0°
ω/2θ scans	h = 0→15
Absorption correction: empirical (using intensity measurements) ψ scan (3 reflections) (North et al., 1968)	k = −10→10
Tmin = 0.299, Tmax = 0.351	l = −23→23
7860 measured reflections	3 standard reflections every 200 reflections
4073 independent reflections	intensity decay: 32%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.051	w = 1/[σ^2(Fo^2) + (0.1112P)^2 + 0.3126P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.142	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.63 e Å^−3
4073 reflections	Δρmin = −0.38 e Å^−3
469 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
8 restraints	Extinction coefficient: 0.0054 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.08 (2)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.46235 (4)	0.62124 (6)	0.22865 (3)	0.0463 (2)
Cl2	0.37580 (17)	0.40168 (18)	0.19192 (8)	0.0858 (5)
Cl3	0.26678 (18)	0.9707 (2)	0.78698 (12)	0.0940 (5)
Cl1	0.75002 (17)	−0.1810 (3)	0.5609 (2)	0.1301 (11)
N1	0.4666 (3)	0.5515 (5)	0.3246 (2)	0.0507 (9)
N2	0.5503 (4)	0.4897 (6)	0.4261 (2)	0.0592 (10)
N3	0.6422 (3)	0.5656 (5)	0.2580 (2)	0.0536 (9)
C1	0.3944 (4)	0.4911 (6)	0.3659 (2)	0.0517 (10)
C2	0.2864 (5)	0.4670 (7)	0.3516 (3)	0.0634 (13)
H2	0.2505	0.4957	0.3096	0.076*
C3	0.2360 (6)	0.3986 (10)	0.4030 (4)	0.085 (2)
H3	0.1649	0.3759	0.3949	0.102*
C4	0.2905 (7)	0.3622 (11)	0.4678 (4)	0.092 (2)
H4	0.2531	0.3203	0.5019	0.111*
C5	0.3943 (7)	0.3859 (10)	0.4819 (4)	0.085 (2)
H5	0.4296	0.3575	0.5241	0.102*
C6	0.4469 (5)	0.4553 (7)	0.4303 (3)	0.0610 (12)
C7	0.5592 (4)	0.5465 (6)	0.3628 (3)	0.0525 (10)
C8	0.6577 (4)	0.5948 (7)	0.3321 (3)	0.0604 (12)
H8A	0.6714	0.7043	0.3407	0.073*
H8B	0.7172	0.5357	0.3528	0.073*
C9	0.6572 (6)	0.3994 (7)	0.2420 (4)	0.0710 (15)
H9A	0.5958	0.3387	0.2501	0.085*
H9B	0.7180	0.3571	0.2694	0.085*
C10	0.6733 (8)	0.4020 (11)	0.1672 (5)	0.095 (2)
H10A	0.6070	0.3864	0.1392	0.113*
H10B	0.7212	0.3202	0.1567	0.113*
C11	0.7182 (7)	0.5584 (13)	0.1525 (4)	0.095 (2)
H11A	0.6731	0.6134	0.1176	0.114*
H11B	0.7875	0.5483	0.1371	0.114*
C12	0.7233 (6)	0.6425 (8)	0.2221 (4)	0.0732 (15)
H12A	0.7919	0.6308	0.2476	0.088*
H12B	0.7081	0.7523	0.2158	0.088*
C13	0.6342 (6)	0.4744 (8)	0.4825 (3)	0.0684 (14)
H13A	0.6132	0.5260	0.5231	0.082*
H13B	0.6967	0.5259	0.4696	0.082*
C14	0.6599 (5)	0.3067 (7)	0.4997 (3)	0.0652 (13)
C15	0.6902 (5)	0.2068 (7)	0.4515 (3)	0.0639 (13)
H15	0.6913	0.2398	0.4061	0.077*
C16	0.7198 (5)	0.0552 (9)	0.4696 (4)	0.0779 (17)
H16	0.7432	−0.0124	0.4372	0.093*
C17	0.7135 (5)	0.0081 (8)	0.5363 (5)	0.081 (2)
C18	0.6787 (7)	0.1037 (10)	0.5853 (4)	0.090 (2)
H18	0.6718	0.0676	0.6296	0.107*
C19	0.6540 (7)	0.2557 (10)	0.5670 (3)	0.088 (2)
H19	0.6332	0.3242	0.5999	0.106*
Cl1A	0.97099 (13)	1.1523 (3)	0.01150 (11)	0.0980 (6)
N1A	0.4622 (3)	0.7177 (4)	0.13661 (19)	0.0475 (8)
N2A	0.4863 (3)	0.9222 (5)	0.0723 (2)	0.0489 (8)
N3A	0.4530 (4)	0.8668 (5)	0.2573 (2)	0.0517 (9)
C1A	0.4551 (4)	0.6703 (6)	0.0682 (2)	0.0484 (9)
C2A	0.4358 (4)	0.5239 (6)	0.0368 (3)	0.0572 (11)
H2A	0.4252	0.4358	0.0628	0.069*
C3A	0.4333 (5)	0.5170 (8)	−0.0337 (3)	0.0673 (14)
H3A	0.4206	0.4217	−0.0555	0.081*
C4A	0.4491 (5)	0.6473 (9)	−0.0739 (3)	0.0710 (15)
H4A	0.4457	0.6369	−0.1216	0.085*
C5A	0.4697 (4)	0.7914 (7)	−0.0446 (3)	0.0610 (12)
H5A	0.4811	0.8784	−0.0712	0.073*
C6A	0.4725 (4)	0.7995 (6)	0.0275 (3)	0.0501 (10)
C7A	0.4802 (4)	0.8678 (5)	0.1364 (3)	0.0458 (9)
C8A	0.4924 (4)	0.9613 (5)	0.2016 (3)	0.0531 (10)
H8A1	0.5656	0.9874	0.2135	0.064*
H8A2	0.4526	1.0570	0.1954	0.064*
C9A	0.4964 (6)	0.9266 (7)	0.3261 (3)	0.0680 (15)
H9A1	0.5704	0.9511	0.3264	0.082*
H9A2	0.4879	0.8507	0.3619	0.082*
C10A	0.4325 (8)	1.0738 (8)	0.3372 (4)	0.087 (2)
H10C	0.4260	1.0904	0.3858	0.105*
H10D	0.4649	1.1645	0.3187	0.105*
C11A	0.3258 (8)	1.0413 (9)	0.2978 (5)	0.097 (3)
H11C	0.3057	1.1252	0.2659	0.117*
H11D	0.2724	1.0304	0.3295	0.117*
C12A	0.3386 (5)	0.8900 (7)	0.2589 (4)	0.0693 (15)
H12C	0.3084	0.8041	0.2823	0.083*
H12D	0.3040	0.8971	0.2124	0.083*
C13A	0.5167 (4)	1.0812 (5)	0.0530 (3)	0.0549 (11)
H13C	0.5023	1.1530	0.0892	0.066*
H13D	0.4746	1.1121	0.0110	0.066*
C14A	0.6311 (4)	1.0910 (5)	0.0418 (3)	0.0487 (9)
C15A	0.7071 (5)	1.0121 (8)	0.0812 (4)	0.0749 (17)
H15A	0.6875	0.9434	0.1144	0.090*
C16A	0.8129 (5)	1.0303 (9)	0.0735 (4)	0.0799 (18)
H16A	0.8639	0.9781	0.1020	0.096*
C17A	0.8398 (4)	1.1281 (7)	0.0225 (3)	0.0615 (12)
C18A	0.7660 (6)	1.2072 (10)	−0.0177 (4)	0.087 (2)
H18A	0.7854	1.2719	−0.0525	0.104*
C19A	0.6617 (5)	1.1915 (9)	−0.0070 (3)	0.0742 (17)
H19A	0.6113	1.2499	−0.0333	0.089*
O1	0.4386 (8)	0.1708 (12)	0.8635 (5)	0.075 (2)*	0.50
H1	0.3784	0.2031	0.8555	0.113*	0.50
C20	0.507 (2)	0.257 (3)	0.8226 (11)	0.162 (11)*	0.50
H20A	0.5765	0.2632	0.8475	0.195*	0.50
H20B	0.4806	0.3618	0.8157	0.195*	0.50
C21	0.515 (2)	0.183 (4)	0.7544 (10)	0.143 (8)*	0.50
H21A	0.5681	0.2342	0.7314	0.214*	0.50
H21B	0.4487	0.1908	0.7268	0.214*	0.50
H21C	0.5332	0.0751	0.7609	0.214*	0.50
O1A	−0.0786 (15)	0.298 (2)	0.2525 (10)	0.140 (5)*	0.50
H1A	−0.0841	0.2573	0.2900	0.211*	0.50
C20A	0.010 (2)	0.231 (3)	0.222 (2)	0.191 (15)*	0.50
H20C	−0.0151	0.1609	0.1850	0.229*	0.50
H20D	0.0531	0.1721	0.2568	0.229*	0.50
C21A	0.072 (2)	0.362 (4)	0.1950 (19)	0.169 (12)*	0.50
H21D	0.1304	0.3205	0.1737	0.254*	0.50
H21E	0.0978	0.4291	0.2325	0.254*	0.50
H21F	0.0281	0.4209	0.1617	0.254*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0565 (4)	0.0345 (3)	0.0483 (3)	−0.0038 (3)	0.0065 (2)	0.0046 (3)
Cl2	0.1281 (15)	0.0611 (8)	0.0686 (8)	−0.0445 (9)	0.0122 (8)	−0.0036 (6)
Cl3	0.1004 (12)	0.0766 (10)	0.1032 (12)	−0.0109 (9)	0.0022 (10)	0.0028 (9)
Cl1	0.0727 (10)	0.0767 (11)	0.237 (3)	0.0019 (9)	−0.0047 (14)	0.0627 (17)
N1	0.052 (2)	0.044 (2)	0.057 (2)	−0.0018 (16)	0.0085 (17)	0.0061 (17)
N2	0.070 (3)	0.057 (2)	0.051 (2)	0.011 (2)	0.0047 (19)	0.0032 (18)
N3	0.056 (2)	0.0408 (18)	0.066 (2)	−0.0024 (17)	0.0152 (18)	0.0007 (17)
C1	0.062 (3)	0.044 (2)	0.051 (2)	0.004 (2)	0.014 (2)	0.0024 (19)
C2	0.059 (3)	0.059 (3)	0.075 (3)	−0.006 (2)	0.020 (2)	−0.003 (2)
C3	0.069 (4)	0.096 (5)	0.096 (5)	−0.018 (3)	0.035 (3)	−0.006 (4)
C4	0.100 (5)	0.109 (6)	0.074 (4)	−0.014 (4)	0.040 (4)	0.011 (4)
C5	0.105 (5)	0.099 (5)	0.054 (3)	−0.004 (4)	0.028 (3)	0.014 (3)
C6	0.079 (4)	0.049 (3)	0.057 (3)	0.006 (2)	0.018 (2)	0.003 (2)
C7	0.060 (3)	0.045 (2)	0.053 (2)	0.007 (2)	0.009 (2)	0.0039 (19)
C8	0.057 (3)	0.056 (3)	0.067 (3)	−0.002 (2)	0.001 (2)	0.005 (2)
C9	0.078 (4)	0.052 (3)	0.085 (4)	0.013 (3)	0.017 (3)	−0.003 (3)
C10	0.105 (6)	0.088 (5)	0.090 (5)	0.014 (4)	0.008 (4)	−0.032 (4)
C11	0.089 (5)	0.122 (7)	0.078 (4)	0.022 (5)	0.033 (4)	0.013 (4)
C12	0.066 (3)	0.071 (4)	0.086 (4)	−0.001 (3)	0.024 (3)	0.005 (3)
C13	0.086 (4)	0.067 (3)	0.050 (2)	0.004 (3)	−0.005 (2)	−0.002 (2)
C14	0.076 (3)	0.059 (3)	0.056 (3)	−0.004 (3)	−0.012 (2)	0.005 (2)
C15	0.065 (3)	0.061 (3)	0.065 (3)	0.006 (3)	0.000 (2)	0.006 (2)
C16	0.057 (3)	0.067 (3)	0.109 (5)	−0.001 (3)	0.005 (3)	−0.002 (3)
C17	0.052 (3)	0.066 (4)	0.120 (6)	−0.002 (3)	−0.017 (3)	0.022 (4)
C18	0.103 (5)	0.089 (5)	0.072 (4)	0.001 (4)	−0.017 (4)	0.029 (4)
C19	0.122 (6)	0.090 (5)	0.050 (3)	0.004 (4)	−0.007 (3)	0.006 (3)
Cl1A	0.0539 (8)	0.1400 (18)	0.1020 (12)	−0.0080 (9)	0.0175 (8)	0.0177 (12)
N1A	0.059 (2)	0.0355 (17)	0.0478 (19)	−0.0018 (15)	0.0028 (16)	0.0048 (15)
N2A	0.053 (2)	0.0383 (18)	0.057 (2)	0.0015 (15)	0.0131 (16)	0.0105 (16)
N3A	0.062 (2)	0.0394 (18)	0.054 (2)	−0.0013 (16)	0.0094 (17)	−0.0013 (15)
C1A	0.050 (2)	0.043 (2)	0.053 (2)	−0.0001 (18)	0.0053 (18)	0.0019 (19)
C2A	0.067 (3)	0.042 (2)	0.062 (3)	−0.002 (2)	0.003 (2)	−0.006 (2)
C3A	0.067 (3)	0.066 (3)	0.068 (3)	0.004 (3)	0.004 (2)	−0.024 (3)
C4A	0.070 (3)	0.091 (4)	0.053 (3)	0.006 (3)	0.009 (2)	−0.007 (3)
C5A	0.064 (3)	0.069 (3)	0.052 (2)	0.008 (2)	0.014 (2)	0.006 (2)
C6A	0.046 (2)	0.051 (2)	0.053 (2)	0.0026 (19)	0.0027 (18)	0.007 (2)
C7A	0.048 (2)	0.033 (2)	0.056 (2)	−0.0001 (16)	0.0059 (18)	0.0045 (17)
C8A	0.068 (3)	0.0336 (19)	0.058 (2)	−0.0017 (19)	0.010 (2)	0.0045 (18)
C9A	0.102 (5)	0.049 (3)	0.052 (3)	0.011 (3)	0.006 (3)	−0.009 (2)
C10A	0.131 (7)	0.052 (3)	0.082 (4)	0.011 (4)	0.030 (4)	−0.012 (3)
C11A	0.114 (6)	0.059 (3)	0.127 (6)	0.027 (4)	0.050 (5)	0.008 (4)
C12A	0.060 (3)	0.057 (3)	0.092 (4)	0.004 (2)	0.018 (3)	0.005 (3)
C13A	0.058 (3)	0.034 (2)	0.074 (3)	−0.0003 (18)	0.011 (2)	0.018 (2)
C14A	0.056 (2)	0.0339 (19)	0.057 (2)	−0.0011 (17)	0.0097 (19)	0.0069 (17)
C15A	0.062 (3)	0.075 (4)	0.091 (4)	0.011 (3)	0.021 (3)	0.043 (3)
C16A	0.061 (3)	0.084 (4)	0.095 (4)	0.009 (3)	0.008 (3)	0.030 (4)
C17A	0.052 (3)	0.068 (3)	0.064 (3)	−0.005 (2)	0.008 (2)	−0.003 (2)
C18A	0.066 (3)	0.107 (5)	0.088 (4)	−0.010 (3)	0.011 (3)	0.048 (4)
C19A	0.067 (3)	0.081 (4)	0.075 (3)	−0.002 (3)	0.005 (3)	0.037 (3)

Geometric parameters (Å, º)

Cu1—N1	1.959 (4)	N3A—C12A	1.482 (8)
Cu1—N1A	1.976 (4)	N3A—C8A	1.485 (7)
Cu1—N3A	2.193 (4)	N3A—C9A	1.490 (7)
Cu1—Cl2	2.2699 (15)	C1A—C6A	1.396 (7)
Cu1—N3	2.366 (5)	C1A—C2A	1.411 (7)
Cl1—C17	1.747 (7)	C2A—C3A	1.372 (9)
N1—C7	1.336 (7)	C2A—H2A	0.9300
N1—C1	1.387 (7)	C3A—C4A	1.395 (11)
N2—C7	1.343 (7)	C3A—H3A	0.9300
N2—C6	1.368 (8)	C4A—C5A	1.380 (10)
N2—C13	1.462 (7)	C4A—H4A	0.9300
N3—C8	1.459 (7)	C5A—C6A	1.404 (7)
N3—C12	1.467 (8)	C5A—H5A	0.9300
N3—C9	1.481 (7)	C7A—C8A	1.499 (7)
C1—C6	1.396 (8)	C8A—H8A1	0.9700
C1—C2	1.399 (8)	C8A—H8A2	0.9700
C2—C3	1.376 (9)	C9A—C10A	1.536 (9)
C2—H2	0.9300	C9A—H9A1	0.9700
C3—C4	1.415 (13)	C9A—H9A2	0.9700
C3—H3	0.9300	C10A—C11A	1.524 (14)
C4—C5	1.347 (14)	C10A—H10C	0.9700
C4—H4	0.9300	C10A—H10D	0.9700
C5—C6	1.400 (9)	C11A—C12A	1.525 (10)
C5—H5	0.9300	C11A—H11C	0.9700
C7—C8	1.508 (8)	C11A—H11D	0.9700
C8—H8A	0.9700	C12A—H12C	0.9700
C8—H8B	0.9700	C12A—H12D	0.9700
C9—C10	1.492 (11)	C13A—C14A	1.504 (7)
C9—H9A	0.9700	C13A—H13C	0.9700
C9—H9B	0.9700	C13A—H13D	0.9700
C10—C11	1.503 (14)	C14A—C15A	1.358 (8)
C10—H10A	0.9700	C14A—C19A	1.372 (7)
C10—H10B	0.9700	C15A—C16A	1.388 (9)
C11—C12	1.533 (12)	C15A—H15A	0.9300
C11—H11A	0.9700	C16A—C17A	1.372 (9)
C11—H11B	0.9700	C16A—H16A	0.9300
C12—H12A	0.9700	C17A—C18A	1.348 (9)
C12—H12B	0.9700	C18A—C19A	1.381 (10)
C13—C14	1.511 (9)	C18A—H18A	0.9300
C13—H13A	0.9700	C19A—H19A	0.9300
C13—H13B	0.9700	O1—C20	1.447 (10)
C14—C15	1.359 (9)	O1—H1	0.8200
C14—C19	1.392 (9)	C20—C21	1.487 (10)
C15—C16	1.394 (10)	C20—H20A	0.9700
C15—H15	0.9300	C20—H20B	0.9700
C16—C17	1.372 (12)	C21—H21A	0.9600
C16—H16	0.9300	C21—H21B	0.9600
C17—C18	1.368 (13)	C21—H21C	0.9600
C18—C19	1.384 (12)	O1A—C20A	1.446 (10)
C18—H18	0.9300	O1A—H1A	0.8200
C19—H19	0.9300	C20A—C21A	1.515 (10)
Cl1A—C17A	1.729 (6)	C20A—H20C	0.9700
N1A—C7A	1.312 (6)	C20A—H20D	0.9700
N1A—C1A	1.389 (6)	C21A—H21D	0.9600
N2A—C7A	1.343 (6)	C21A—H21E	0.9600
N2A—C6A	1.370 (7)	C21A—H21F	0.9600
N2A—C13A	1.482 (6)
N1—Cu1—N1A	172.84 (18)	C8A—N3A—C9A	110.2 (4)
N1—Cu1—N3A	92.82 (17)	C12A—N3A—Cu1	102.4 (3)
N1A—Cu1—N3A	80.27 (17)	C8A—N3A—Cu1	108.1 (3)
N1—Cu1—Cl2	90.64 (13)	C9A—N3A—Cu1	122.5 (3)
N1A—Cu1—Cl2	96.22 (12)	N1A—C1A—C6A	108.2 (4)
N3A—Cu1—Cl2	147.71 (14)	N1A—C1A—C2A	132.1 (4)
N1—Cu1—N3	77.00 (16)	C6A—C1A—C2A	119.7 (5)
N1A—Cu1—N3	102.47 (16)	C3A—C2A—C1A	117.3 (5)
N3A—Cu1—N3	102.16 (16)	C3A—C2A—H2A	121.4
Cl2—Cu1—N3	109.89 (12)	C1A—C2A—H2A	121.4
C7—N1—C1	105.8 (4)	C2A—C3A—C4A	122.5 (5)
C7—N1—Cu1	118.6 (3)	C2A—C3A—H3A	118.8
C1—N1—Cu1	135.5 (4)	C4A—C3A—H3A	118.8
C7—N2—C6	107.8 (5)	C5A—C4A—C3A	121.6 (5)
C7—N2—C13	126.7 (5)	C5A—C4A—H4A	119.2
C6—N2—C13	125.4 (5)	C3A—C4A—H4A	119.2
C8—N3—C12	111.2 (5)	C4A—C5A—C6A	116.3 (5)
C8—N3—C9	111.6 (5)	C4A—C5A—H5A	121.9
C12—N3—C9	102.9 (5)	C6A—C5A—H5A	121.9
C8—N3—Cu1	103.6 (3)	N2A—C6A—C1A	105.7 (4)
C12—N3—Cu1	120.8 (4)	N2A—C6A—C5A	131.6 (5)
C9—N3—Cu1	106.8 (4)	C1A—C6A—C5A	122.6 (5)
N1—C1—C6	108.3 (5)	N1A—C7A—N2A	111.9 (4)
N1—C1—C2	130.1 (5)	N1A—C7A—C8A	121.9 (4)
C6—C1—C2	121.6 (5)	N2A—C7A—C8A	126.1 (4)
C3—C2—C1	116.4 (6)	N3A—C8A—C7A	108.2 (4)
C3—C2—H2	121.8	N3A—C8A—H8A1	110.1
C1—C2—H2	121.8	C7A—C8A—H8A1	110.1
C2—C3—C4	121.3 (7)	N3A—C8A—H8A2	110.1
C2—C3—H3	119.4	C7A—C8A—H8A2	110.1
C4—C3—H3	119.4	H8A1—C8A—H8A2	108.4
C5—C4—C3	122.4 (6)	N3A—C9A—C10A	104.8 (6)
C5—C4—H4	118.8	N3A—C9A—H9A1	110.8
C3—C4—H4	118.8	C10A—C9A—H9A1	110.8
C4—C5—C6	117.1 (7)	N3A—C9A—H9A2	110.8
C4—C5—H5	121.5	C10A—C9A—H9A2	110.8
C6—C5—H5	121.5	H9A1—C9A—H9A2	108.9
N2—C6—C1	106.3 (5)	C11A—C10A—C9A	104.0 (6)
N2—C6—C5	132.4 (6)	C11A—C10A—H10C	111.0
C1—C6—C5	121.1 (6)	C9A—C10A—H10C	111.0
N1—C7—N2	111.7 (5)	C11A—C10A—H10D	111.0
N1—C7—C8	120.1 (4)	C9A—C10A—H10D	111.0
N2—C7—C8	128.1 (5)	H10C—C10A—H10D	109.0
N3—C8—C7	108.0 (4)	C10A—C11A—C12A	105.7 (6)
N3—C8—H8A	110.1	C10A—C11A—H11C	110.6
C7—C8—H8A	110.1	C12A—C11A—H11C	110.6
N3—C8—H8B	110.1	C10A—C11A—H11D	110.6
C7—C8—H8B	110.1	C12A—C11A—H11D	110.6
H8A—C8—H8B	108.4	H11C—C11A—H11D	108.7
N3—C9—C10	103.0 (6)	N3A—C12A—C11A	106.4 (6)
N3—C9—H9A	111.2	N3A—C12A—H12C	110.4
C10—C9—H9A	111.2	C11A—C12A—H12C	110.4
N3—C9—H9B	111.2	N3A—C12A—H12D	110.4
C10—C9—H9B	111.2	C11A—C12A—H12D	110.4
H9A—C9—H9B	109.1	H12C—C12A—H12D	108.6
C9—C10—C11	107.0 (6)	N2A—C13A—C14A	111.9 (4)
C9—C10—H10A	110.3	N2A—C13A—H13C	109.2
C11—C10—H10A	110.3	C14A—C13A—H13C	109.2
C9—C10—H10B	110.3	N2A—C13A—H13D	109.2
C11—C10—H10B	110.3	C14A—C13A—H13D	109.2
H10A—C10—H10B	108.6	H13C—C13A—H13D	107.9
C10—C11—C12	103.7 (6)	C15A—C14A—C19A	117.9 (5)
C10—C11—H11A	111.0	C15A—C14A—C13A	122.9 (5)
C12—C11—H11A	111.0	C19A—C14A—C13A	119.1 (5)
C10—C11—H11B	111.0	C14A—C15A—C16A	122.3 (5)
C12—C11—H11B	111.0	C14A—C15A—H15A	118.8
H11A—C11—H11B	109.0	C16A—C15A—H15A	118.8
N3—C12—C11	103.9 (6)	C17A—C16A—C15A	117.8 (6)
N3—C12—H12A	111.0	C17A—C16A—H16A	121.1
C11—C12—H12A	111.0	C15A—C16A—H16A	121.1
N3—C12—H12B	111.0	C18A—C17A—C16A	121.2 (6)
C11—C12—H12B	111.0	C18A—C17A—Cl1A	120.0 (5)
H12A—C12—H12B	109.0	C16A—C17A—Cl1A	118.8 (5)
N2—C13—C14	112.3 (5)	C17A—C18A—C19A	119.6 (6)
N2—C13—H13A	109.1	C17A—C18A—H18A	120.2
C14—C13—H13A	109.1	C19A—C18A—H18A	120.2
N2—C13—H13B	109.1	C14A—C19A—C18A	121.0 (6)
C14—C13—H13B	109.1	C14A—C19A—H19A	119.5
H13A—C13—H13B	107.9	C18A—C19A—H19A	119.5
C15—C14—C19	119.9 (6)	C20—O1—H1	109.5
C15—C14—C13	121.5 (5)	O1—C20—C21	111.8 (11)
C19—C14—C13	118.7 (6)	O1—C20—H20A	109.3
C14—C15—C16	120.4 (6)	C21—C20—H20A	109.3
C14—C15—H15	119.8	O1—C20—H20B	109.3
C16—C15—H15	119.8	C21—C20—H20B	109.3
C17—C16—C15	118.4 (7)	H20A—C20—H20B	107.9
C17—C16—H16	120.8	C20—C21—H21A	109.5
C15—C16—H16	120.8	C20—C21—H21B	109.5
C18—C17—C16	122.5 (6)	H21A—C21—H21B	109.5
C18—C17—Cl1	117.8 (6)	C20—C21—H21C	109.5
C16—C17—Cl1	119.7 (7)	H21A—C21—H21C	109.5
C17—C18—C19	118.1 (7)	H21B—C21—H21C	109.5
C17—C18—H18	121.0	C20A—O1A—H1A	109.5
C19—C18—H18	121.0	O1A—C20A—C21A	107.8 (10)
C18—C19—C14	120.5 (8)	O1A—C20A—H20C	110.1
C18—C19—H19	119.7	C21A—C20A—H20C	110.1
C14—C19—H19	119.7	O1A—C20A—H20D	110.1
C7A—N1A—C1A	106.3 (4)	C21A—C20A—H20D	110.1
C7A—N1A—Cu1	115.7 (3)	H20C—C20A—H20D	108.5
C1A—N1A—Cu1	137.9 (3)	C20A—C21A—H21D	109.5
C7A—N2A—C6A	107.9 (4)	C20A—C21A—H21E	109.5
C7A—N2A—C13A	126.9 (4)	H21D—C21A—H21E	109.5
C6A—N2A—C13A	124.8 (4)	C20A—C21A—H21F	109.5
C12A—N3A—C8A	110.5 (5)	H21D—C21A—H21F	109.5
C12A—N3A—C9A	102.4 (5)	H21E—C21A—H21F	109.5
N1A—Cu1—N1—C7	−70.4 (16)	N1—Cu1—N1A—C7A	−1.2 (17)
N3A—Cu1—N1—C7	−85.7 (4)	N3A—Cu1—N1A—C7A	14.4 (4)
Cl2—Cu1—N1—C7	126.4 (4)	Cl2—Cu1—N1A—C7A	161.9 (3)
N3—Cu1—N1—C7	16.1 (3)	N3—Cu1—N1A—C7A	−86.1 (4)
N1A—Cu1—N1—C1	115.3 (14)	N1—Cu1—N1A—C1A	173.1 (13)
N3A—Cu1—N1—C1	100.0 (5)	N3A—Cu1—N1A—C1A	−171.4 (5)
Cl2—Cu1—N1—C1	−47.9 (5)	Cl2—Cu1—N1A—C1A	−23.8 (5)
N3—Cu1—N1—C1	−158.2 (5)	N3—Cu1—N1A—C1A	88.2 (5)
N1—Cu1—N3—C8	−29.3 (3)	N1—Cu1—N3A—C12A	−86.7 (4)
N1A—Cu1—N3—C8	143.4 (3)	N1A—Cu1—N3A—C12A	95.2 (4)
N3A—Cu1—N3—C8	60.9 (3)	Cl2—Cu1—N3A—C12A	9.0 (5)
Cl2—Cu1—N3—C8	−115.2 (3)	N3—Cu1—N3A—C12A	−164.0 (4)
N1—Cu1—N3—C12	−154.6 (5)	N1—Cu1—N3A—C8A	156.6 (4)
N1A—Cu1—N3—C12	18.1 (5)	N1A—Cu1—N3A—C8A	−21.5 (3)
N3A—Cu1—N3—C12	−64.5 (4)	Cl2—Cu1—N3A—C8A	−107.7 (4)
Cl2—Cu1—N3—C12	119.5 (4)	N3—Cu1—N3A—C8A	79.3 (4)
N1—Cu1—N3—C9	88.7 (4)	N1—Cu1—N3A—C9A	27.0 (5)
N1A—Cu1—N3—C9	−98.7 (4)	N1A—Cu1—N3A—C9A	−151.1 (5)
N3A—Cu1—N3—C9	178.8 (4)	Cl2—Cu1—N3A—C9A	122.7 (4)
Cl2—Cu1—N3—C9	2.8 (4)	N3—Cu1—N3A—C9A	−50.3 (5)
C7—N1—C1—C6	1.9 (5)	C7A—N1A—C1A—C6A	1.4 (5)
Cu1—N1—C1—C6	176.7 (4)	Cu1—N1A—C1A—C6A	−173.2 (4)
C7—N1—C1—C2	−178.9 (5)	C7A—N1A—C1A—C2A	−179.2 (6)
Cu1—N1—C1—C2	−4.0 (9)	Cu1—N1A—C1A—C2A	6.1 (9)
N1—C1—C2—C3	177.5 (6)	N1A—C1A—C2A—C3A	179.6 (5)
C6—C1—C2—C3	−3.3 (9)	C6A—C1A—C2A—C3A	−1.1 (8)
C1—C2—C3—C4	3.0 (11)	C1A—C2A—C3A—C4A	0.1 (9)
C2—C3—C4—C5	−2.9 (14)	C2A—C3A—C4A—C5A	0.9 (10)
C3—C4—C5—C6	2.7 (13)	C3A—C4A—C5A—C6A	−0.8 (9)
C7—N2—C6—C1	1.2 (6)	C7A—N2A—C6A—C1A	1.5 (5)
C13—N2—C6—C1	178.2 (5)	C13A—N2A—C6A—C1A	174.1 (4)
C7—N2—C6—C5	175.8 (7)	C7A—N2A—C6A—C5A	178.7 (5)
C13—N2—C6—C5	−7.2 (11)	C13A—N2A—C6A—C5A	−8.7 (8)
N1—C1—C6—N2	−1.9 (6)	N1A—C1A—C6A—N2A	−1.8 (5)
C2—C1—C6—N2	178.8 (5)	C2A—C1A—C6A—N2A	178.8 (5)
N1—C1—C6—C5	−177.3 (6)	N1A—C1A—C6A—C5A	−179.4 (4)
C2—C1—C6—C5	3.4 (9)	C2A—C1A—C6A—C5A	1.2 (7)
C4—C5—C6—N2	−176.9 (7)	C4A—C5A—C6A—N2A	−177.1 (5)
C4—C5—C6—C1	−2.9 (11)	C4A—C5A—C6A—C1A	−0.2 (8)
C1—N1—C7—N2	−1.2 (6)	C1A—N1A—C7A—N2A	−0.5 (6)
Cu1—N1—C7—N2	−177.1 (3)	Cu1—N1A—C7A—N2A	175.5 (3)
C1—N1—C7—C8	176.3 (5)	C1A—N1A—C7A—C8A	179.8 (4)
Cu1—N1—C7—C8	0.4 (6)	Cu1—N1A—C7A—C8A	−4.2 (6)
C6—N2—C7—N1	0.0 (6)	C6A—N2A—C7A—N1A	−0.6 (6)
C13—N2—C7—N1	−177.0 (5)	C13A—N2A—C7A—N1A	−173.0 (4)
C6—N2—C7—C8	−177.2 (5)	C6A—N2A—C7A—C8A	179.0 (5)
C13—N2—C7—C8	5.8 (9)	C13A—N2A—C7A—C8A	6.6 (8)
C12—N3—C8—C7	166.6 (5)	C12A—N3A—C8A—C7A	−87.6 (5)
C9—N3—C8—C7	−79.2 (6)	C9A—N3A—C8A—C7A	160.0 (4)
Cu1—N3—C8—C7	35.3 (5)	Cu1—N3A—C8A—C7A	23.8 (5)
N1—C7—C8—N3	−28.2 (7)	N1A—C7A—C8A—N3A	−14.9 (7)
N2—C7—C8—N3	148.8 (5)	N2A—C7A—C8A—N3A	165.5 (5)
C8—N3—C9—C10	−162.2 (6)	C12A—N3A—C9A—C10A	−41.1 (6)
C12—N3—C9—C10	−42.9 (7)	C8A—N3A—C9A—C10A	76.5 (6)
Cu1—N3—C9—C10	85.3 (6)	Cu1—N3A—C9A—C10A	−154.8 (5)
N3—C9—C10—C11	26.9 (9)	N3A—C9A—C10A—C11A	30.1 (7)
C9—C10—C11—C12	−1.4 (9)	C9A—C10A—C11A—C12A	−7.5 (8)
C8—N3—C12—C11	161.7 (5)	C8A—N3A—C12A—C11A	−81.0 (6)
C9—N3—C12—C11	42.2 (7)	C9A—N3A—C12A—C11A	36.4 (6)
Cu1—N3—C12—C11	−76.5 (6)	Cu1—N3A—C12A—C11A	164.1 (5)
C10—C11—C12—N3	−24.9 (8)	C10A—C11A—C12A—N3A	−17.7 (8)
C7—N2—C13—C14	−112.9 (6)	C7A—N2A—C13A—C14A	96.1 (6)
C6—N2—C13—C14	70.7 (7)	C6A—N2A—C13A—C14A	−75.0 (6)
N2—C13—C14—C15	57.8 (8)	N2A—C13A—C14A—C15A	−37.8 (8)
N2—C13—C14—C19	−123.4 (7)	N2A—C13A—C14A—C19A	146.7 (6)
C19—C14—C15—C16	−2.8 (10)	C19A—C14A—C15A—C16A	0.1 (11)
C13—C14—C15—C16	176.0 (6)	C13A—C14A—C15A—C16A	−175.4 (7)
C14—C15—C16—C17	2.5 (9)	C14A—C15A—C16A—C17A	−2.3 (13)
C15—C16—C17—C18	0.6 (10)	C15A—C16A—C17A—C18A	1.8 (12)
C15—C16—C17—Cl1	−179.9 (5)	C15A—C16A—C17A—Cl1A	−179.7 (6)
C16—C17—C18—C19	−3.3 (12)	C16A—C17A—C18A—C19A	0.8 (13)
Cl1—C17—C18—C19	177.3 (6)	Cl1A—C17A—C18A—C19A	−177.7 (7)
C17—C18—C19—C14	3.0 (13)	C15A—C14A—C19A—C18A	2.6 (11)
C15—C14—C19—C18	0.0 (12)	C13A—C14A—C19A—C18A	178.3 (7)
C13—C14—C19—C18	−178.8 (7)	C17A—C18A—C19A—C14A	−3.1 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl3^i	0.82	2.73	3.061 (10)	106
O1A—H1A···Cl3^ii	0.82	2.73	3.16 (2)	114

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