Dichloro­bis(3,5-dimethyl­pyrazole)copper(II)

The title compound, [CuCl₂(C₅H₈N₂)₂], has been synthesized as part of a project aimed at the synthesis and characterization of scorpionate ligands with cyano substituents. The structure shows the Cu ion coordinated by two 3,5-dimethyl­pyrazole ligands and two chloride ligands in a tetrahedral coordination geometry.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.067
• wR factor = 0.211
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.98 Deg.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.449     0.696
            Tmin' and Tmax expected:      0.574     0.696
            RR' =      0.782
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.77
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu     -   Cl1     ..       7.03 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu     -   Cl2     ..       5.86 su
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         16

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

   0 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
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Dichlorobis(3,5-dimethylpyrazole)copper(II)

Crystal data

[CuCl2(C5H8N2)2]	F(000) = 1336
Mr = 326.71	Dx = 1.461 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.023 (6) Å	Cell parameters from 24 reflections
b = 8.270 (7) Å	θ = 10–12°
c = 24.038 (7) Å	µ = 1.82 mm^−1
β = 96.03 (3)°	T = 150 K
V = 2970 (3) Å^3	Prism, blue
Z = 8	0.3 × 0.2 × 0.2 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.076
non–profiled ω/2θ scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: psi scan (North et al., 1968)	h = 0→17
Tmin = 0.449, Tmax = 0.696	k = 0→9
2697 measured reflections	l = −28→28
2607 independent reflections	3 standard reflections every 60 min
1907 reflections with I > 2σ(I)	intensity decay: −2%

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.067	w = 1/[σ^2(Fo^2) + (0.1478P)^2 + 1.1566P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.211	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.93 e Å^−3
2607 reflections	Δρmin = −1.14 e Å^−3
158 parameters

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
Cu	0.88335 (5)	0.22234 (10)	0.12178 (3)	0.0513 (3)
Cl2	0.82529 (14)	0.0906 (2)	0.04530 (7)	0.0725 (6)
Cl1	1.00026 (11)	0.1103 (2)	0.17329 (7)	0.0704 (6)
N2	0.8222 (3)	0.2496 (6)	0.23562 (19)	0.0494 (12)
H004	0.8732	0.2153	0.2505	0.059*
N1	0.7991 (3)	0.2608 (6)	0.17996 (18)	0.0442 (11)
N4	0.8810 (4)	0.4772 (7)	0.03617 (19)	0.0551 (13)
H006	0.8573	0.4085	0.0121	0.066*
N3	0.9060 (3)	0.4415 (6)	0.09000 (19)	0.0493 (12)
C3	0.7151 (4)	0.3173 (7)	0.1744 (2)	0.0485 (14)
C8	0.9396 (4)	0.5776 (8)	0.1128 (2)	0.0527 (14)
C1	0.7560 (4)	0.2983 (8)	0.2648 (3)	0.0545 (15)
C2	0.6873 (4)	0.3403 (8)	0.2265 (3)	0.0552 (15)
H011	0.6315	0.3779	0.2341	0.066*
C7	0.9338 (5)	0.6988 (8)	0.0725 (3)	0.0611 (17)
H012	0.9519	0.8058	0.0778	0.073*
C6	0.8970 (4)	0.6317 (8)	0.0242 (3)	0.0562 (15)
C10	0.9738 (6)	0.5851 (9)	0.1735 (3)	0.075 (2)
H01A	0.9294	0.5426	0.1955	0.113*
H01B	0.9864	0.6954	0.184	0.113*
H01C	1.0275	0.5221	0.18	0.113*
C5	0.6677 (5)	0.3453 (11)	0.1176 (3)	0.075 (2)
H01D	0.7083	0.3924	0.0939	0.113*
H01E	0.6182	0.4173	0.1203	0.113*
H01F	0.6459	0.2441	0.102	0.113*
C9	0.8743 (6)	0.6994 (10)	−0.0335 (3)	0.079 (2)
H01G	0.866	0.6123	−0.0599	0.119*
H01H	0.9222	0.7676	−0.0428	0.119*
H01I	0.8201	0.7614	−0.0345	0.119*
C4	0.7682 (6)	0.3006 (12)	0.3274 (3)	0.084 (3)
H01J	0.7197	0.2433	0.3416	0.127*
H01K	0.7687	0.4105	0.3403	0.127*
H01L	0.8238	0.2496	0.3405	0.127*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.0528 (5)	0.0514 (5)	0.0472 (5)	0.0073 (3)	−0.0068 (3)	−0.0021 (3)
Cl2	0.0966 (13)	0.0534 (10)	0.0600 (10)	0.0120 (9)	−0.0275 (9)	−0.0164 (8)
Cl1	0.0584 (10)	0.0875 (13)	0.0601 (10)	0.0322 (9)	−0.0177 (7)	−0.0074 (9)
N2	0.050 (3)	0.053 (3)	0.042 (3)	0.006 (2)	−0.009 (2)	0.003 (2)
N1	0.044 (3)	0.049 (3)	0.038 (2)	0.006 (2)	−0.0026 (19)	0.003 (2)
N4	0.070 (3)	0.058 (3)	0.034 (2)	−0.002 (3)	−0.005 (2)	−0.004 (2)
N3	0.055 (3)	0.051 (3)	0.039 (2)	0.000 (2)	−0.007 (2)	0.002 (2)
C3	0.046 (3)	0.046 (3)	0.052 (3)	0.008 (3)	0.000 (2)	0.002 (3)
C8	0.055 (3)	0.053 (4)	0.047 (3)	0.005 (3)	−0.006 (3)	−0.005 (3)
C1	0.056 (4)	0.056 (4)	0.051 (3)	0.005 (3)	0.004 (3)	−0.003 (3)
C2	0.046 (3)	0.061 (4)	0.058 (4)	0.013 (3)	0.004 (3)	−0.004 (3)
C7	0.068 (4)	0.049 (4)	0.063 (4)	0.000 (3)	−0.007 (3)	0.005 (3)
C6	0.058 (4)	0.059 (4)	0.050 (3)	0.000 (3)	−0.002 (3)	0.010 (3)
C10	0.097 (6)	0.064 (4)	0.058 (4)	−0.009 (4)	−0.025 (4)	−0.006 (3)
C5	0.059 (4)	0.108 (6)	0.056 (4)	0.035 (4)	−0.008 (3)	−0.009 (4)
C9	0.095 (6)	0.086 (6)	0.056 (4)	0.008 (4)	0.003 (4)	0.020 (4)
C4	0.089 (6)	0.111 (7)	0.051 (4)	0.020 (5)	0.002 (4)	−0.006 (4)

Geometric parameters (Å, º)

Cu—N1	2.007 (5)	C1—C4	1.498 (8)
Cu—N3	2.010 (5)	C2—H011	0.93
Cu—Cl2	2.2340 (18)	C7—C6	1.353 (9)
Cu—Cl1	2.2404 (18)	C7—H012	0.93
N2—C1	1.336 (8)	C6—C9	1.500 (9)
N2—N1	1.350 (6)	C10—H01A	0.96
N2—H004	0.86	C10—H01B	0.96
N1—C3	1.340 (7)	C10—H01C	0.96
N4—C6	1.338 (9)	C5—H01D	0.96
N4—N3	1.342 (6)	C5—H01E	0.96
N4—H006	0.86	C5—H01F	0.96
N3—C8	1.328 (8)	C9—H01G	0.96
C3—C2	1.375 (8)	C9—H01H	0.96
C3—C5	1.489 (8)	C9—H01I	0.96
C8—C7	1.391 (9)	C4—H01J	0.96
C8—C10	1.496 (8)	C4—H01K	0.96
C1—C2	1.355 (8)	C4—H01L	0.96
N1—Cu—N3	105.5 (2)	C6—C7—C8	107.0 (6)
N1—Cu—Cl2	115.49 (15)	C6—C7—H012	126.5
N3—Cu—Cl2	101.20 (15)	C8—C7—H012	126.5
N1—Cu—Cl1	101.26 (14)	N4—C6—C7	105.9 (5)
N3—Cu—Cl1	115.39 (15)	N4—C6—C9	121.8 (6)
Cl2—Cu—Cl1	117.95 (8)	C7—C6—C9	132.3 (7)
C1—N2—N1	111.8 (5)	C8—C10—H01A	109.5
C1—N2—H004	124.1	C8—C10—H01B	109.5
N1—N2—H004	124.1	H01A—C10—H01B	109.5
C3—N1—N2	105.3 (4)	C8—C10—H01C	109.5
C3—N1—Cu	129.9 (4)	H01A—C10—H01C	109.5
N2—N1—Cu	124.4 (4)	H01B—C10—H01C	109.5
C6—N4—N3	112.3 (5)	C3—C5—H01D	109.5
C6—N4—H006	123.9	C3—C5—H01E	109.5
N3—N4—H006	123.9	H01D—C5—H01E	109.5
C8—N3—N4	105.6 (5)	C3—C5—H01F	109.5
C8—N3—Cu	132.8 (4)	H01D—C5—H01F	109.5
N4—N3—Cu	121.5 (4)	H01E—C5—H01F	109.5
N1—C3—C2	109.3 (5)	C6—C9—H01G	109.5
N1—C3—C5	120.1 (5)	C6—C9—H01H	109.5
C2—C3—C5	130.7 (6)	H01G—C9—H01H	109.5
N3—C8—C7	109.3 (5)	C6—C9—H01I	109.5
N3—C8—C10	121.0 (6)	H01G—C9—H01I	109.5
C7—C8—C10	129.7 (6)	H01H—C9—H01I	109.5
N2—C1—C2	106.1 (5)	C1—C4—H01J	109.5
N2—C1—C4	120.8 (6)	C1—C4—H01K	109.5
C2—C1—C4	133.1 (6)	H01J—C4—H01K	109.5
C1—C2—C3	107.5 (5)	C1—C4—H01L	109.5
C1—C2—H011	126.3	H01J—C4—H01L	109.5
C3—C2—H011	126.3	H01K—C4—H01L	109.5