Dichloro­bis[2-chloro-5-(chloro­meth­yl)pyridine]copper(II)

In the title compound, [CuCl₂(C₆H₅Cl₂N)₂], each Cu atom has a distorted tetra­hedral coordination involving two Cl⁻ anions and two 2-chloro-5-(chloro­meth­yl)pyridine ligands. The mol­ecular structure and packing are stabilized by intra- and intermolecular C—H...Cl hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.053
• wR factor = 0.169
• Data-to-parameter ratio = 19.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT220_ALERT_2_C Large Non-Solvent   Cl     Ueq(max)/Ueq(min) ...       2.91 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        Cl6
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

Dichlorobis[2-chloro-5-(chloromethyl)pyridine]copper(II)

Crystal data

[CuCl2(C12H10N2)2]	F(000) = 1816
Mr = 916.94	Dx = 1.778 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 16.699 (4) Å	θ = 4–14°
b = 14.981 (5) Å	µ = 2.20 mm^−1
c = 15.205 (3) Å	T = 293 K
β = 115.74 (3)°	Block, green
V = 3426.4 (18) Å^3	0.25 × 0.20 × 0.18 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	2778 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
Graphite monochromator	θmax = 27.0°, θmin = 1.9°
ω scans	h = −21→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→19
Tmin = 0.595, Tmax = 0.673	l = −18→18
7596 measured reflections	3 standard reflections every 100 reflections
3689 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.169	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0948P)^2 + 8.8566P] where P = (Fo^2 + 2Fc^2)/3
3689 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 1.53 e Å^−3
0 restraints	Δρmin = −0.97 e Å^−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	0.38296 (3)	0.10515 (3)	0.23934 (4)	0.0404 (2)
Cl1	0.55341 (15)	−0.30657 (13)	0.42789 (16)	0.1049 (7)
Cl2	0.25520 (9)	−0.03386 (9)	0.06419 (10)	0.0686 (4)
Cl3	0.43767 (7)	0.11627 (7)	0.12487 (8)	0.0433 (3)
Cl4	0.32302 (9)	0.10336 (8)	0.34666 (11)	0.0617 (4)
Cl5	0.55431 (12)	0.43986 (18)	0.40611 (18)	0.1259 (10)
Cl6	0.20978 (8)	0.19182 (9)	0.07463 (11)	0.0679 (4)
N1	0.3851 (2)	−0.0331 (2)	0.2412 (3)	0.0413 (8)
N2	0.3553 (2)	0.2391 (2)	0.2249 (3)	0.0431 (8)
C1	0.3289 (3)	−0.0850 (3)	0.1691 (3)	0.0454 (10)
C2	0.3265 (4)	−0.1774 (3)	0.1766 (4)	0.0575 (12)
H2A	0.2864	−0.2114	0.1252	0.069*
C3	0.3846 (4)	−0.2171 (3)	0.2616 (4)	0.0573 (12)
H3A	0.3846	−0.2788	0.2680	0.069*
C4	0.4427 (3)	−0.1659 (3)	0.3372 (4)	0.0494 (10)
C5	0.4410 (3)	−0.0743 (3)	0.3239 (3)	0.0464 (10)
H5A	0.4806	−0.0394	0.3748	0.056*
C6	0.5037 (4)	−0.2032 (4)	0.4361 (4)	0.0681 (15)
H6A	0.4699	−0.2124	0.4735	0.082*
H6B	0.5501	−0.1601	0.4709	0.082*
C7	0.2811 (3)	0.2702 (3)	0.1533 (3)	0.0476 (10)
C8	0.2571 (3)	0.3595 (3)	0.1412 (4)	0.0554 (12)
H8A	0.2061	0.3792	0.0882	0.067*
C9	0.3116 (3)	0.4176 (3)	0.2099 (4)	0.0585 (13)
H9A	0.2980	0.4781	0.2043	0.070*
C10	0.3876 (3)	0.3870 (3)	0.2887 (4)	0.0503 (11)
C11	0.4075 (3)	0.2981 (3)	0.2910 (3)	0.0475 (10)
H11A	0.4603	0.2778	0.3410	0.057*
C12	0.4431 (4)	0.4509 (4)	0.3678 (5)	0.0734 (16)
H12A	0.4298	0.4429	0.4234	0.088*
H12B	0.4262	0.5113	0.3440	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0404 (3)	0.0287 (3)	0.0509 (3)	−0.00185 (18)	0.0186 (2)	−0.00168 (19)
Cl1	0.1303 (16)	0.0797 (11)	0.1183 (15)	0.0502 (11)	0.0666 (13)	0.0447 (10)
Cl2	0.0612 (8)	0.0547 (7)	0.0636 (8)	−0.0074 (6)	0.0025 (6)	−0.0001 (6)
Cl3	0.0402 (5)	0.0397 (5)	0.0465 (6)	0.0033 (4)	0.0156 (4)	0.0023 (4)
Cl4	0.0700 (8)	0.0499 (7)	0.0818 (9)	−0.0182 (5)	0.0485 (7)	−0.0119 (6)
Cl5	0.0596 (9)	0.155 (2)	0.1358 (18)	−0.0020 (11)	0.0169 (10)	−0.0823 (16)
Cl6	0.0492 (7)	0.0629 (8)	0.0739 (9)	−0.0002 (6)	0.0102 (6)	−0.0095 (6)
N1	0.0399 (18)	0.0327 (17)	0.050 (2)	−0.0033 (13)	0.0183 (16)	−0.0018 (14)
N2	0.0426 (18)	0.0350 (17)	0.050 (2)	0.0036 (14)	0.0184 (16)	−0.0002 (15)
C1	0.045 (2)	0.037 (2)	0.052 (3)	−0.0040 (18)	0.020 (2)	−0.0033 (18)
C2	0.068 (3)	0.036 (2)	0.066 (3)	−0.012 (2)	0.028 (3)	−0.014 (2)
C3	0.078 (3)	0.028 (2)	0.066 (3)	−0.003 (2)	0.031 (3)	−0.003 (2)
C4	0.050 (2)	0.040 (2)	0.062 (3)	0.0026 (19)	0.028 (2)	0.006 (2)
C5	0.044 (2)	0.041 (2)	0.051 (2)	−0.0066 (18)	0.018 (2)	−0.0039 (19)
C6	0.075 (4)	0.055 (3)	0.071 (4)	0.013 (3)	0.028 (3)	0.016 (3)
C7	0.043 (2)	0.046 (2)	0.052 (2)	0.0059 (18)	0.019 (2)	0.0005 (19)
C8	0.048 (2)	0.047 (2)	0.070 (3)	0.013 (2)	0.024 (2)	0.009 (2)
C9	0.062 (3)	0.036 (2)	0.086 (4)	0.016 (2)	0.040 (3)	0.009 (2)
C10	0.055 (3)	0.038 (2)	0.062 (3)	0.0012 (19)	0.029 (2)	−0.004 (2)
C11	0.048 (2)	0.038 (2)	0.051 (3)	0.0026 (18)	0.016 (2)	−0.0019 (18)
C12	0.074 (4)	0.048 (3)	0.094 (4)	−0.003 (3)	0.033 (3)	−0.022 (3)

Geometric parameters (Å, º)

Cu1—N2	2.048 (4)	C3—H3A	0.9300
Cu1—N1	2.071 (4)	C4—C5	1.386 (6)
Cu1—Cl4	2.2548 (14)	C4—C6	1.510 (7)
Cu1—Cl3	2.2965 (13)	C5—H5A	0.9300
Cl1—C6	1.786 (6)	C6—H6A	0.9699
Cl2—C1	1.715 (5)	C6—H6B	0.9700
Cl5—C12	1.695 (6)	C7—C8	1.386 (6)
Cl6—C7	1.729 (5)	C8—C9	1.360 (8)
N1—C1	1.339 (5)	C8—H8A	0.9299
N1—C5	1.347 (6)	C9—C10	1.390 (7)
N2—C7	1.330 (6)	C9—H9A	0.9300
N2—C11	1.338 (6)	C10—C11	1.369 (6)
C1—C2	1.391 (6)	C10—C12	1.502 (7)
C2—C3	1.369 (7)	C11—H11A	0.9300
C2—H2A	0.9300	C12—H12A	0.9699
C3—C4	1.373 (7)	C12—H12B	0.9701
N2—Cu1—N1	169.17 (14)	C4—C6—Cl1	112.6 (4)
N2—Cu1—Cl4	86.58 (11)	C4—C6—H6A	108.9
N1—Cu1—Cl4	89.26 (11)	Cl1—C6—H6A	108.8
N2—Cu1—Cl3	89.53 (11)	C4—C6—H6B	109.3
N1—Cu1—Cl3	94.26 (10)	Cl1—C6—H6B	109.3
Cl4—Cu1—Cl3	175.71 (5)	H6A—C6—H6B	107.8
C1—N1—C5	116.9 (4)	N2—C7—C8	124.0 (4)
C1—N1—Cu1	124.6 (3)	N2—C7—Cl6	116.5 (3)
C5—N1—Cu1	118.2 (3)	C8—C7—Cl6	119.5 (4)
C7—N2—C11	117.1 (4)	C9—C8—C7	117.2 (5)
C7—N2—Cu1	121.2 (3)	C9—C8—H8A	121.3
C11—N2—Cu1	121.6 (3)	C7—C8—H8A	121.5
N1—C1—C2	123.0 (4)	C8—C9—C10	120.5 (4)
N1—C1—Cl2	117.8 (3)	C8—C9—H9A	119.9
C2—C1—Cl2	119.1 (4)	C10—C9—H9A	119.7
C3—C2—C1	118.5 (4)	C11—C10—C9	117.6 (5)
C3—C2—H2A	120.8	C11—C10—C12	122.7 (5)
C1—C2—H2A	120.8	C9—C10—C12	119.7 (4)
C2—C3—C4	120.0 (4)	N2—C11—C10	123.5 (4)
C2—C3—H3A	120.0	N2—C11—H11A	118.3
C4—C3—H3A	120.0	C10—C11—H11A	118.2
C3—C4—C5	117.9 (4)	C10—C12—Cl5	114.7 (4)
C3—C4—C6	123.6 (4)	C10—C12—H12A	108.8
C5—C4—C6	118.3 (4)	Cl5—C12—H12A	108.6
N1—C5—C4	123.6 (4)	C10—C12—H12B	108.5
N1—C5—H5A	118.2	Cl5—C12—H12B	108.5
C4—C5—H5A	118.2	H12A—C12—H12B	107.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cl3^i	0.93	2.70	3.390 (5)	131
C6—H6B···Cl4^ii	0.97	2.79	3.636 (6)	146
C9—H9A···Cl4^iii	0.93	2.62	3.444 (5)	149
C11—H11A···Cl5	0.93	2.83	3.140 (5)	101

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