Chloridotetra­kis(imidazole)copper(II) chloride

The title compound, [CuCl(C₃H₃N₂)₄]Cl, exhibits a square-pyramidal coordination of Cu^II by four N atoms of four imidazole ligands and one chlorine atom located at the apex of the pyramid.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.025
• wR factor = 0.072
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

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Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         13
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  N8      ..       3.24 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  N2      ..       3.16 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  N4      ..       3.23 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  N6      ..       3.24 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          9
            N5  -CU1 -N3  -C4   -148.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         13
            N5  -CU1 -N3  -C6     27.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         17
            N3  -CU1 -N5  -C7    157.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         21
            N3  -CU1 -N5  -C9    -20.00  3.00   1.555   1.555   1.555   1.555

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       2.19
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
   9 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level G
PUBL013_ALERT_1_G The _publ_section_comment (discussion of study) is
            missing. This is required for a full paper submission (but is
            optional for an electronic paper).

   0 ALERT level A = Data missing that is essential or data in wrong format
   1 ALERT level G = General alerts. Data that may be required is missing

---

Related literature

For related literature see Li et al. (2004).

Please provide a caption for Figure 1; CIF refers to a packing diagram (`Figure 2'), which was not included in the submission.

S1. Experimental

The aimed compound was prepared by adding imidazole (27.2 mg, 0.4 mmol) to a solution of CuCl₂2H₂O (17.2 mg, 0.1 mmol) in CH₃OH and stirred vigorously for about 4 h, then the blue precipitate were filtered off and dried in vacuum. Single crystals suitable for X-ray structural analysis were obtained from DMF solution by slow evaporation. The crystal packing (Fig. 2) involves C—H···Cl hydrogen bonds formed between CH of the imidazole group and the coordinated chlorine (C8—H8···Cl1ⁱ with C8···Cl1ⁱ of 3.806 (2) Å; H8···Cl1ⁱof 2.878 (2) Å; C8—H8—Cl1ⁱ = 175.3 (2) °; symmetry code i = 1/2 - x, 1/2 + y, 1/2 - z) generating a chain along the axis b.

Structure description

For related literature see Li et al. (2004).

Please provide a caption for Figure 1; CIF refers to a packing diagram (`Figure 2'), which was not included in the submission.

Computing details

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

Figures

Fig. 1. Molecular structure of the title compound with ellipsoids drawn at the 30% probability level.

Chloridotetrakis(imidazole)copper(II) chloride

Crystal data

[CuCl(C3H3N2)4]Cl	F(000) = 812
Mr = 402.74	Dx = 1.627 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8636 reflections
a = 8.8662 (3) Å	θ = 2.7–27.4°
b = 13.3199 (4) Å	µ = 1.66 mm^−1
c = 13.9190 (4) Å	T = 293 K
β = 90.042 (1)°	Block, blue
V = 1643.79 (9) Å^3	0.15 × 0.12 × 0.10 mm
Z = 4

Data collection

Bruker AXS CCD area-detector diffractometer	2885 independent reflections
Radiation source: fine-focus sealed tube	2735 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
phi and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→8
Tmin = 0.788, Tmax = 0.851	k = −15→15
18750 measured reflections	l = −16→16

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.072	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0522P)^2 + 0.4934P] where P = (Fo^2 + 2Fc^2)/3
2885 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.56 e Å^−3
1 restraint	Δρmin = −0.31 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	0.68669 (11)	0.21337 (6)	0.37745 (7)	0.0240 (4)
Cl1	0.4436 (2)	0.10148 (15)	0.37916 (18)	0.0334 (5)
Cl2	0.0547 (2)	0.40803 (17)	0.37502 (18)	0.0368 (5)
N1	0.5854 (8)	0.3488 (5)	0.3741 (5)	0.0277 (14)
N2	0.4028 (8)	0.4602 (5)	0.3706 (6)	0.0353 (17)
N3	0.6950 (9)	0.2209 (5)	0.5209 (5)	0.0286 (16)
N4	0.6740 (10)	0.1813 (6)	0.6730 (5)	0.0383 (19)
N5	0.6957 (9)	0.2123 (5)	0.2342 (5)	0.0273 (16)
N6	0.6674 (10)	0.1741 (6)	0.0824 (5)	0.0354 (18)
N7	0.8583 (8)	0.1139 (5)	0.3799 (6)	0.0276 (15)
N8	1.0860 (8)	0.0512 (6)	0.3744 (7)	0.0389 (17)
C1	0.6476 (10)	0.4434 (6)	0.3757 (7)	0.036 (2)
H1	0.7503	0.4576	0.3777	0.043*
C2	0.5353 (10)	0.5125 (7)	0.3739 (8)	0.040 (2)
H2	0.5463	0.5819	0.3747	0.047*
C3	0.4385 (10)	0.3618 (6)	0.3713 (7)	0.0313 (18)
H3	0.3684	0.3099	0.3701	0.038*
C4	0.6407 (11)	0.1555 (7)	0.5825 (7)	0.034 (2)
H4	0.5862	0.0985	0.5654	0.040*
C5	0.7553 (13)	0.2692 (8)	0.6689 (7)	0.042 (2)
H5	0.7941	0.3050	0.7206	0.050*
C6	0.7675 (12)	0.2930 (7)	0.5751 (7)	0.036 (2)
H6	0.8169	0.3491	0.5508	0.043*
C7	0.6289 (11)	0.1510 (7)	0.1729 (7)	0.033 (2)
H7	0.5643	0.0991	0.1901	0.039*
C8	0.7656 (13)	0.2535 (8)	0.0856 (7)	0.039 (2)
H8	0.8116	0.2852	0.0338	0.047*
C9	0.7816 (12)	0.2764 (6)	0.1798 (7)	0.034 (2)
H9	0.8417	0.3277	0.2040	0.041*
C10	1.0017 (10)	0.1352 (7)	0.3754 (8)	0.036 (2)
H10	1.0406	0.1999	0.3732	0.043*
C11	0.9878 (11)	−0.0278 (7)	0.3794 (9)	0.043 (2)
H11	1.0129	−0.0956	0.3802	0.052*
C12	0.8481 (10)	0.0114 (6)	0.3829 (7)	0.036 (2)
H12	0.7590	−0.0253	0.3868	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0257 (6)	0.0258 (5)	0.0206 (5)	0.0039 (4)	0.0002 (5)	0.0001 (4)
Cl1	0.0294 (11)	0.0342 (11)	0.0366 (12)	−0.0065 (8)	−0.0001 (11)	0.0031 (10)
Cl2	0.0312 (11)	0.0486 (12)	0.0305 (11)	0.0088 (9)	0.0003 (11)	0.0022 (11)
N1	0.030 (4)	0.028 (3)	0.025 (3)	0.003 (3)	0.001 (4)	0.000 (3)
N2	0.032 (4)	0.033 (4)	0.041 (4)	0.006 (3)	0.000 (4)	−0.001 (4)
N3	0.029 (4)	0.032 (4)	0.024 (4)	0.004 (3)	0.000 (3)	0.000 (3)
N4	0.036 (5)	0.055 (5)	0.024 (4)	0.003 (4)	0.001 (4)	0.006 (4)
N5	0.028 (4)	0.029 (4)	0.025 (4)	0.005 (3)	−0.001 (3)	−0.002 (3)
N6	0.033 (4)	0.047 (5)	0.026 (4)	0.004 (4)	0.000 (3)	−0.006 (3)
N7	0.027 (4)	0.030 (3)	0.026 (3)	0.002 (3)	0.000 (3)	0.000 (3)
N8	0.028 (4)	0.048 (4)	0.041 (4)	0.008 (3)	0.000 (4)	0.003 (4)
C1	0.029 (4)	0.031 (4)	0.047 (5)	−0.002 (3)	−0.001 (5)	0.000 (5)
C2	0.037 (5)	0.025 (4)	0.057 (6)	−0.001 (4)	−0.002 (5)	0.000 (5)
C3	0.030 (5)	0.032 (4)	0.032 (5)	−0.001 (4)	−0.001 (4)	0.000 (4)
C4	0.031 (5)	0.036 (5)	0.033 (5)	0.001 (4)	−0.001 (4)	0.005 (4)
C5	0.040 (6)	0.058 (6)	0.028 (5)	−0.002 (5)	−0.004 (5)	−0.007 (4)
C6	0.038 (6)	0.037 (5)	0.033 (5)	−0.005 (4)	−0.002 (4)	0.001 (4)
C7	0.030 (5)	0.035 (5)	0.033 (5)	0.002 (4)	−0.001 (4)	−0.004 (4)
C8	0.048 (6)	0.042 (5)	0.028 (4)	0.004 (5)	0.007 (4)	0.006 (4)
C9	0.039 (6)	0.033 (5)	0.030 (5)	−0.005 (4)	0.006 (4)	0.001 (4)
C10	0.035 (5)	0.032 (4)	0.041 (5)	0.001 (4)	0.001 (5)	0.002 (4)
C11	0.045 (6)	0.033 (5)	0.052 (6)	0.010 (4)	0.000 (5)	−0.001 (5)
C12	0.031 (5)	0.030 (4)	0.048 (5)	0.000 (3)	0.001 (5)	−0.001 (4)

Geometric parameters (Å, º)

Cu1—N5	1.996 (7)	N8—C10	1.346 (12)
Cu1—N3	2.000 (7)	N8—C11	1.367 (13)
Cu1—N1	2.016 (6)	C1—C2	1.356 (13)
Cu1—N7	2.018 (7)	C1—H1	0.9300
Cu1—Cl1	2.621 (2)	C2—H2	0.9300
N1—C3	1.314 (12)	C3—H3	0.9300
N1—C1	1.375 (11)	C4—H4	0.9300
N2—C3	1.348 (11)	C5—C6	1.348 (14)
N2—C2	1.367 (12)	C5—H5	0.9300
N3—C4	1.314 (12)	C6—H6	0.9300
N3—C6	1.380 (12)	C7—H7	0.9300
N4—C4	1.338 (12)	C8—C9	1.353 (13)
N4—C5	1.376 (14)	C8—H8	0.9300
N5—C7	1.320 (12)	C9—H9	0.9300
N5—C9	1.372 (12)	C10—H10	0.9300
N6—C7	1.341 (12)	C11—C12	1.345 (13)
N6—C8	1.370 (15)	C11—H11	0.9300
N7—C10	1.304 (11)	C12—H12	0.9300
N7—C12	1.369 (11)
N5—Cu1—N3	174.9 (3)	N2—C2—H2	126.7
N5—Cu1—N1	90.1 (3)	N1—C3—N2	111.1 (8)
N3—Cu1—N1	89.7 (3)	N1—C3—H3	124.4
N5—Cu1—N7	88.9 (3)	N2—C3—H3	124.4
N3—Cu1—N7	89.3 (3)	N3—C4—N4	111.3 (8)
N1—Cu1—N7	157.5 (3)	N3—C4—H4	124.4
N5—Cu1—Cl1	92.2 (2)	N4—C4—H4	124.4
N3—Cu1—Cl1	92.8 (2)	C6—C5—N4	106.4 (9)
N1—Cu1—Cl1	98.2 (2)	C6—C5—H5	126.8
N7—Cu1—Cl1	104.3 (2)	N4—C5—H5	126.8
C3—N1—C1	106.1 (7)	C5—C6—N3	109.1 (9)
C3—N1—Cu1	124.0 (6)	C5—C6—H6	125.4
C1—N1—Cu1	129.8 (6)	N3—C6—H6	125.4
C3—N2—C2	107.1 (7)	N5—C7—N6	110.5 (8)
C4—N3—C6	106.0 (8)	N5—C7—H7	124.7
C4—N3—Cu1	127.2 (6)	N6—C7—H7	124.7
C6—N3—Cu1	126.7 (6)	C9—C8—N6	105.7 (8)
C4—N4—C5	107.2 (8)	C9—C8—H8	127.1
C7—N5—C9	106.1 (8)	N6—C8—H8	127.1
C7—N5—Cu1	129.2 (6)	C8—C9—N5	109.7 (8)
C9—N5—Cu1	124.7 (6)	C8—C9—H9	125.2
C7—N6—C8	108.0 (7)	N5—C9—H9	125.2
C10—N7—C12	106.4 (8)	N7—C10—N8	111.2 (8)
C10—N7—Cu1	126.3 (6)	N7—C10—H10	124.4
C12—N7—Cu1	127.3 (6)	N8—C10—H10	124.4
C10—N8—C11	106.6 (7)	C12—C11—N8	106.8 (8)
C2—C1—N1	109.1 (8)	C12—C11—H11	126.6
C2—C1—H1	125.5	N8—C11—H11	126.6
N1—C1—H1	125.5	C11—C12—N7	109.0 (8)
C1—C2—N2	106.6 (7)	C11—C12—H12	125.5
C1—C2—H2	126.7	N7—C12—H12	125.5
N5—Cu1—N1—C3	90.8 (8)	N1—Cu1—N7—C12	179.6 (8)
N3—Cu1—N1—C3	−94.3 (8)	Cl1—Cu1—N7—C12	−0.7 (8)
N7—Cu1—N1—C3	178.2 (8)	C3—N1—C1—C2	0.0 (12)
Cl1—Cu1—N1—C3	−1.5 (8)	Cu1—N1—C1—C2	−178.9 (7)
N5—Cu1—N1—C1	−90.4 (8)	N1—C1—C2—N2	−0.4 (12)
N3—Cu1—N1—C1	84.5 (8)	C3—N2—C2—C1	0.5 (12)
N7—Cu1—N1—C1	−3.0 (13)	C1—N1—C3—N2	0.3 (12)
Cl1—Cu1—N1—C1	177.3 (8)	Cu1—N1—C3—N2	179.4 (6)
N5—Cu1—N3—C4	−148 (3)	C2—N2—C3—N1	−0.5 (12)
N1—Cu1—N3—C4	124.3 (8)	C6—N3—C4—N4	0.0 (11)
N7—Cu1—N3—C4	−78.2 (8)	Cu1—N3—C4—N4	176.4 (7)
Cl1—Cu1—N3—C4	26.1 (8)	C5—N4—C4—N3	−0.1 (12)
N5—Cu1—N3—C6	27 (3)	C4—N4—C5—C6	0.1 (12)
N1—Cu1—N3—C6	−60.1 (8)	N4—C5—C6—N3	−0.1 (12)
N7—Cu1—N3—C6	97.4 (8)	C4—N3—C6—C5	0.1 (12)
Cl1—Cu1—N3—C6	−158.3 (8)	Cu1—N3—C6—C5	−176.3 (7)
N3—Cu1—N5—C7	157 (3)	C9—N5—C7—N6	−0.7 (10)
N1—Cu1—N5—C7	−115.8 (8)	Cu1—N5—C7—N6	−178.4 (6)
N7—Cu1—N5—C7	86.6 (8)	C8—N6—C7—N5	0.9 (11)
Cl1—Cu1—N5—C7	−17.6 (8)	C7—N6—C8—C9	−0.6 (12)
N3—Cu1—N5—C9	−20 (3)	N6—C8—C9—N5	0.2 (12)
N1—Cu1—N5—C9	66.9 (7)	C7—N5—C9—C8	0.3 (11)
N7—Cu1—N5—C9	−90.7 (7)	Cu1—N5—C9—C8	178.1 (7)
Cl1—Cu1—N5—C9	165.1 (7)	C12—N7—C10—N8	0.6 (12)
N5—Cu1—N7—C10	84.6 (9)	Cu1—N7—C10—N8	−177.2 (6)
N3—Cu1—N7—C10	−90.6 (9)	C11—N8—C10—N7	−0.5 (13)
N1—Cu1—N7—C10	−3.0 (15)	C10—N8—C11—C12	0.2 (13)
Cl1—Cu1—N7—C10	176.7 (9)	N8—C11—C12—N7	0.2 (13)
N5—Cu1—N7—C12	−92.7 (8)	C10—N7—C12—C11	−0.5 (12)
N3—Cu1—N7—C12	92.1 (8)	Cu1—N7—C12—C11	177.3 (8)