Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041864/hg2282sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041864/hg2282Isup2.hkl |
CCDC reference: 663548
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.056
- wR factor = 0.140
- Data-to-parameter ratio = 9.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.70 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.73 Ratio PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu1 - Cl1 .. 18.26 su
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 Cl
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 25.97 From the CIF: _reflns_number_total 2811 Count of symmetry unique reflns 2599 Completeness (_total/calc) 108.16% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 212 Fraction of Friedel pairs measured 0.082 Are heavy atom types Z>Si present yes PLAT033_ALERT_2_G Flack Parameter Value Deviates 2 * su from zero. 0.09 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) 2.12 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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
The title compound was prepared by the reaction of 1-ethylimidazole (1.92 g, 20 mmol) with CuCl2.2H2O (0.68 g, 5 mmol) by means of hydrothermal synthesis in a stainless-steel reactor with Teflon liner at 383 K for 24 h. Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.
H atoms bonded to O were located in a difference map and their coordinates were refined with Uiso(H)=1.2Ueq(O). The other H atoms were positioned geometrically (C—H = 0.93 Å) and allowed to ride on their attached atoms Uiso(H) = 1.2–1.5Ueq(C).
In title compound, the crystal structure consists of discrete CuCl(Eim)4+ cations, Cl- anions and water molecules. The CuII ion adopts a distorted square pyramidal geometry. The basal coordination positions are occupied by the N atoms of the Eim ligands with bond lengths ranging from 1.960 (7) to 2.075 (8) Å, and the apical position by a Cl anion [Cu—Cl = 2.730 (3) Å], while another chloride anion in the general position balances the charges. All these values agree well with two polymorphism complexes [CuCl(im)4Cl](im is 1H-imidazole) (Otieno et al., 2001; Jian et al., 2004). In the crystal, the title compound form three-dimensional hydrogen bond networks to stabilize the structure.
For related literature, see: Jian et al. (2004); Otieno et al. (2001).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2001) and local programs.
Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. | |
Fig. 2. The packing of (I), viewed down the c axis. |
[CuCl(C5H8N2)4]Cl·H2O | F(000) = 1124 |
Mr = 537.00 | Dx = 1.352 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 3489 reflections |
a = 20.304 (4) Å | θ = 2.1–26.0° |
b = 8.6090 (17) Å | µ = 1.06 mm−1 |
c = 17.364 (4) Å | T = 293 K |
β = 119.65 (3)° | Block, blue |
V = 2637.8 (12) Å3 | 0.20 × 0.10 × 0.10 mm |
Z = 4 |
Bruker SMART 1K CCD area-detector diffractometer | 2811 independent reflections |
Radiation source: fine-focus sealed tube | 2013 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
thin–slice ω scans | θmax = 26.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −21→25 |
Tmin = 0.816, Tmax = 0.902 | k = 0→10 |
5104 measured reflections | l = −21→0 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.056 | w = 1/[σ2(Fo2) + (0.0852P)2 + 0.8132P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.140 | (Δ/σ)max = 0.007 |
S = 0.95 | Δρmax = 0.77 e Å−3 |
2811 reflections | Δρmin = −0.48 e Å−3 |
302 parameters | Extinction correction: SHELXTL (Sheldrick, 2001), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
6 restraints | Extinction coefficient: 0.0042 (6) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 212 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.09 (3) |
[CuCl(C5H8N2)4]Cl·H2O | V = 2637.8 (12) Å3 |
Mr = 537.00 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 20.304 (4) Å | µ = 1.06 mm−1 |
b = 8.6090 (17) Å | T = 293 K |
c = 17.364 (4) Å | 0.20 × 0.10 × 0.10 mm |
β = 119.65 (3)° |
Bruker SMART 1K CCD area-detector diffractometer | 2811 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 2013 reflections with I > 2σ(I) |
Tmin = 0.816, Tmax = 0.902 | Rint = 0.022 |
5104 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.140 | Δρmax = 0.77 e Å−3 |
S = 0.95 | Δρmin = −0.48 e Å−3 |
2811 reflections | Absolute structure: Flack (1983), with 212 Friedel pairs |
302 parameters | Absolute structure parameter: 0.09 (3) |
6 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.45278 (5) | 0.93673 (12) | −0.00119 (6) | 0.0418 (3) | |
Cl1 | 0.33081 (13) | 0.7876 (3) | −0.13405 (17) | 0.0541 (7) | |
Cl2 | 0.6087 (2) | 1.1185 (3) | 0.1607 (2) | 0.0711 (9) | |
O1W | 0.2390 (5) | 0.6153 (12) | −0.3198 (5) | 0.074 (2) | |
N1 | 0.3969 (4) | 0.9903 (9) | 0.0603 (5) | 0.0382 (16) | |
N2 | 0.3177 (5) | 0.9711 (11) | 0.1131 (6) | 0.054 (2) | |
N3 | 0.4954 (4) | 0.7458 (8) | 0.0708 (5) | 0.0396 (17) | |
N4 | 0.5781 (4) | 0.5894 (8) | 0.1720 (4) | 0.0358 (16) | |
N5 | 0.5177 (4) | 0.9008 (10) | −0.0617 (5) | 0.0402 (18) | |
N6 | 0.6119 (4) | 0.8808 (10) | −0.0866 (6) | 0.050 (2) | |
N7 | 0.4203 (4) | 1.1413 (8) | −0.0680 (5) | 0.0379 (17) | |
N8 | 0.4220 (4) | 1.3575 (8) | −0.1323 (5) | 0.0427 (18) | |
C1 | 0.3511 (2) | 0.8971 (3) | 0.0729 (2) | 0.059 (3) | |
H1A | 0.3429 | 0.7932 | 0.0561 | 0.070* | |
C2 | 0.3413 (2) | 1.1234 (3) | 0.1246 (2) | 0.060 (3) | |
H2A | 0.3266 | 1.2036 | 0.1488 | 0.073* | |
C3 | 0.3899 (2) | 1.1316 (3) | 0.0935 (2) | 0.054 (3) | |
H3A | 0.4158 | 1.2212 | 0.0942 | 0.065* | |
C4 | 0.2617 (2) | 0.9038 (3) | 0.1347 (2) | 0.084 (4) | |
H4A | 0.2658 | 0.7915 | 0.1361 | 0.100* | |
H4B | 0.2731 | 0.9385 | 0.1932 | 0.100* | |
C5 | 0.1842 (2) | 0.948 (2) | 0.0704 (2) | 0.103 (6) | |
H5A | 0.1494 | 0.8758 | 0.0729 | 0.154* | |
H5B | 0.1782 | 0.9481 | 0.0120 | 0.154* | |
H5C | 0.1741 | 1.0506 | 0.0841 | 0.154* | |
C6 | 0.5594 (5) | 0.7375 (3) | 0.1456 (2) | 0.045 (2) | |
H6A | 0.5883 | 0.8232 | 0.1765 | 0.054* | |
C7 | 0.5227 (5) | 0.4971 (3) | 0.1093 (6) | 0.0364 (18) | |
H7A | 0.5202 | 0.3893 | 0.1092 | 0.044* | |
C8 | 0.4722 (5) | 0.5951 (3) | 0.0473 (6) | 0.040 (2) | |
H8A | 0.4282 | 0.5649 | −0.0036 | 0.048* | |
C9 | 0.6465 (5) | 0.5343 (3) | 0.2516 (2) | 0.052 (2) | |
H9A | 0.6568 | 0.4284 | 0.2415 | 0.063* | |
H9B | 0.6892 | 0.5977 | 0.2604 | 0.063* | |
C10 | 0.6412 (2) | 0.5384 (3) | 0.3314 (2) | 0.083 (4) | |
H10A | 0.6893 | 0.5115 | 0.3812 | 0.125* | |
H10B | 0.6035 | 0.4655 | 0.3264 | 0.125* | |
H10C | 0.6272 | 0.6410 | 0.3395 | 0.125* | |
C11 | 0.5895 (5) | 0.8847 (3) | −0.0262 (2) | 0.047 (2) | |
H11A | 0.6222 | 0.8768 | 0.0345 | 0.056* | |
C12 | 0.5497 (2) | 0.8989 (3) | −0.1665 (2) | 0.056 (3) | |
H12A | 0.5476 | 0.9031 | −0.2212 | 0.067* | |
C13 | 0.4905 (2) | 0.9099 (3) | −0.1509 (2) | 0.054 (3) | |
H13A | 0.4399 | 0.9216 | −0.1939 | 0.065* | |
C14 | 0.6896 (2) | 0.8680 (3) | −0.0699 (2) | 0.084 (4) | |
H14A | 0.6883 | 0.8400 | −0.1248 | 0.101* | |
H14B | 0.7148 | 0.7847 | −0.0278 | 0.101* | |
C15 | 0.7343 (2) | 1.0112 (3) | −0.0352 (2) | 0.139 (8) | |
H15A | 0.7862 | 0.9907 | −0.0180 | 0.208* | |
H15B | 0.7311 | 1.0466 | 0.0153 | 0.208* | |
H15C | 0.7146 | 1.0898 | −0.0803 | 0.208* | |
C16 | 0.4634 (5) | 1.2435 (3) | −0.0789 (6) | 0.042 (2) | |
H16A | 0.5158 | 1.2366 | −0.0526 | 0.051* | |
C17 | 0.3478 (2) | 1.3303 (3) | −0.1580 (3) | 0.050 (2) | |
H17A | 0.3062 | 1.3907 | −0.1955 | 0.059* | |
C18 | 0.3478 (5) | 1.1944 (3) | −0.1164 (6) | 0.046 (2) | |
H18A | 0.3051 | 1.1464 | −0.1206 | 0.056* | |
C19 | 0.4487 (7) | 1.4891 (3) | −0.1631 (7) | 0.057 (3) | |
H19A | 0.5032 | 1.4987 | −0.1261 | 0.069* | |
H19B | 0.4257 | 1.5840 | −0.1572 | 0.069* | |
C20 | 0.4292 (2) | 1.4693 (3) | −0.2577 (3) | 0.077 (4) | |
H20A | 0.4537 | 1.5490 | −0.2732 | 0.115* | |
H20B | 0.3753 | 1.4770 | −0.2955 | 0.115* | |
H20C | 0.4462 | 1.3692 | −0.2653 | 0.115* | |
H1WB | 0.275 (5) | 0.649 (18) | −0.271 (4) | 0.11 (6)* | |
H1WA | 0.202 (4) | 0.587 (13) | −0.314 (7) | 0.07 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0530 (6) | 0.0326 (5) | 0.0509 (6) | 0.0144 (6) | 0.0343 (5) | 0.0132 (6) |
Cl1 | 0.0377 (12) | 0.0500 (15) | 0.0566 (15) | 0.0011 (11) | 0.0096 (11) | −0.0051 (12) |
Cl2 | 0.108 (2) | 0.0346 (13) | 0.088 (2) | 0.0124 (14) | 0.0623 (19) | 0.0071 (13) |
O1W | 0.052 (5) | 0.105 (7) | 0.056 (5) | −0.017 (5) | 0.019 (4) | 0.000 (5) |
N1 | 0.040 (4) | 0.039 (4) | 0.045 (4) | 0.003 (4) | 0.029 (3) | 0.010 (4) |
N2 | 0.058 (5) | 0.069 (6) | 0.053 (5) | 0.013 (5) | 0.043 (5) | 0.007 (5) |
N3 | 0.043 (4) | 0.037 (4) | 0.037 (4) | 0.002 (3) | 0.018 (4) | −0.001 (3) |
N4 | 0.035 (4) | 0.032 (4) | 0.034 (4) | −0.002 (3) | 0.012 (3) | 0.004 (3) |
N5 | 0.041 (4) | 0.044 (4) | 0.037 (4) | 0.014 (4) | 0.021 (4) | −0.001 (4) |
N6 | 0.041 (4) | 0.053 (5) | 0.055 (5) | 0.003 (4) | 0.024 (4) | −0.001 (4) |
N7 | 0.040 (4) | 0.031 (4) | 0.047 (4) | 0.005 (3) | 0.025 (4) | 0.002 (3) |
N8 | 0.060 (5) | 0.030 (4) | 0.042 (4) | 0.004 (3) | 0.028 (4) | 0.006 (3) |
C1 | 0.072 (7) | 0.048 (6) | 0.073 (7) | 0.009 (5) | 0.050 (6) | 0.018 (5) |
C2 | 0.064 (6) | 0.065 (7) | 0.054 (6) | 0.007 (6) | 0.030 (6) | −0.015 (5) |
C3 | 0.057 (6) | 0.056 (6) | 0.056 (6) | −0.015 (5) | 0.033 (5) | −0.025 (5) |
C4 | 0.109 (11) | 0.079 (9) | 0.107 (11) | 0.011 (8) | 0.088 (10) | 0.024 (8) |
C5 | 0.066 (9) | 0.161 (19) | 0.086 (10) | −0.015 (9) | 0.042 (8) | 0.005 (10) |
C6 | 0.036 (5) | 0.035 (5) | 0.057 (6) | −0.002 (4) | 0.017 (5) | −0.010 (5) |
C7 | 0.040 (4) | 0.027 (4) | 0.043 (5) | −0.001 (4) | 0.021 (4) | −0.003 (4) |
C8 | 0.043 (5) | 0.041 (5) | 0.028 (4) | −0.015 (4) | 0.011 (4) | −0.011 (4) |
C9 | 0.041 (5) | 0.054 (6) | 0.047 (6) | 0.007 (4) | 0.012 (4) | 0.011 (5) |
C10 | 0.062 (7) | 0.124 (13) | 0.048 (7) | 0.017 (8) | 0.016 (6) | 0.026 (8) |
C11 | 0.032 (5) | 0.061 (6) | 0.044 (5) | 0.004 (4) | 0.017 (4) | 0.002 (5) |
C12 | 0.075 (8) | 0.053 (7) | 0.046 (6) | 0.008 (5) | 0.036 (6) | 0.001 (5) |
C13 | 0.062 (6) | 0.058 (6) | 0.044 (5) | 0.014 (5) | 0.029 (5) | 0.006 (5) |
C14 | 0.081 (9) | 0.082 (9) | 0.113 (11) | 0.000 (7) | 0.066 (9) | 0.001 (8) |
C15 | 0.085 (11) | 0.106 (12) | 0.24 (3) | −0.042 (10) | 0.096 (15) | −0.025 (17) |
C16 | 0.038 (5) | 0.046 (5) | 0.044 (5) | 0.009 (4) | 0.021 (4) | 0.011 (4) |
C17 | 0.047 (5) | 0.045 (6) | 0.052 (6) | 0.014 (5) | 0.021 (5) | 0.010 (5) |
C18 | 0.038 (5) | 0.046 (5) | 0.057 (6) | 0.003 (4) | 0.025 (5) | 0.006 (5) |
C19 | 0.089 (8) | 0.036 (5) | 0.070 (7) | 0.000 (5) | 0.058 (6) | 0.007 (5) |
C20 | 0.094 (9) | 0.079 (9) | 0.080 (8) | 0.013 (7) | 0.060 (8) | 0.028 (7) |
Cu1—N1 | 1.960 (7) | C5—H5A | 0.9600 |
Cu1—N3 | 1.986 (7) | C5—H5B | 0.9600 |
Cu1—N7 | 2.031 (7) | C5—H5C | 0.9600 |
Cu1—N5 | 2.075 (8) | C6—H6A | 0.9300 |
Cu1—Cl1 | 2.730 (3) | C7—C8 | 1.353 (13) |
O1W—H1WB | 0.85 (10) | C7—H7A | 0.9300 |
O1W—H1WA | 0.84 (10) | C8—H8A | 0.9300 |
N1—C1 | 1.327 (13) | C9—C10 | 1.442 (7) |
N1—C3 | 1.383 (13) | C9—H9A | 0.9700 |
N2—C1 | 1.348 (13) | C9—H9B | 0.9700 |
N2—C2 | 1.377 (15) | C10—H10A | 0.9600 |
N2—C4 | 1.480 (14) | C10—H10B | 0.9600 |
N3—C6 | 1.308 (12) | C10—H10C | 0.9600 |
N3—C8 | 1.372 (11) | C11—H11A | 0.9300 |
N4—C6 | 1.345 (11) | C12—C13 | 1.360 (6) |
N4—C7 | 1.368 (11) | C12—H12A | 0.9300 |
N4—C9 | 1.471 (12) | C13—H13A | 0.9300 |
N5—C11 | 1.279 (11) | C14—C15 | 1.472 (4) |
N5—C13 | 1.366 (13) | C14—H14A | 0.9700 |
N6—C11 | 1.334 (13) | C14—H14B | 0.9700 |
N6—C12 | 1.346 (14) | C15—H15A | 0.9600 |
N6—C14 | 1.459 (14) | C15—H15B | 0.9600 |
N7—C16 | 1.318 (11) | C15—H15C | 0.9600 |
N7—C18 | 1.364 (11) | C16—H16A | 0.9300 |
N8—C16 | 1.326 (11) | C17—C18 | 1.375 (6) |
N8—C17 | 1.363 (12) | C17—H17A | 0.9300 |
N8—C19 | 1.465 (12) | C18—H18A | 0.9300 |
C1—H1A | 0.9300 | C19—C20 | 1.499 (17) |
C2—C3 | 1.341 (6) | C19—H19A | 0.9700 |
C2—H2A | 0.9300 | C19—H19B | 0.9700 |
C3—H3A | 0.9300 | C20—H20A | 0.9600 |
C4—C5 | 1.459 (7) | C20—H20B | 0.9600 |
C4—H4A | 0.9700 | C20—H20C | 0.9600 |
C4—H4B | 0.9700 | ||
N1—Cu1—N3 | 92.4 (3) | C8—C7—H7A | 127.1 |
N1—Cu1—N7 | 89.8 (3) | N4—C7—H7A | 127.1 |
N3—Cu1—N7 | 174.0 (3) | C7—C8—N3 | 109.8 (7) |
N1—Cu1—N5 | 174.3 (4) | C7—C8—H8A | 125.1 |
N3—Cu1—N5 | 90.4 (3) | N3—C8—H8A | 125.1 |
N7—Cu1—N5 | 87.0 (3) | C10—C9—N4 | 114.2 (9) |
N1—Cu1—Cl1 | 92.5 (2) | C10—C9—H9A | 108.7 |
N3—Cu1—Cl1 | 94.2 (2) | N4—C9—H9A | 108.7 |
N7—Cu1—Cl1 | 91.3 (2) | C10—C9—H9B | 108.7 |
N5—Cu1—Cl1 | 92.3 (2) | N4—C9—H9B | 108.7 |
H1WB—O1W—H1WA | 111 (10) | H9A—C9—H9B | 107.6 |
C1—N1—C3 | 103.8 (8) | C9—C10—H10A | 109.5 |
C1—N1—Cu1 | 126.2 (7) | C9—C10—H10B | 109.5 |
C3—N1—Cu1 | 129.8 (6) | H10A—C10—H10B | 109.5 |
C1—N2—C2 | 107.4 (9) | C9—C10—H10C | 109.5 |
C1—N2—C4 | 126.3 (10) | H10A—C10—H10C | 109.5 |
C2—N2—C4 | 126.2 (10) | H10B—C10—H10C | 109.5 |
C6—N3—C8 | 105.7 (8) | N5—C11—N6 | 112.0 (9) |
C6—N3—Cu1 | 125.4 (6) | N5—C11—H11A | 124.0 |
C8—N3—Cu1 | 128.1 (6) | N6—C11—H11A | 124.0 |
C6—N4—C7 | 107.3 (7) | N6—C12—C13 | 105.9 (9) |
C6—N4—C9 | 127.0 (7) | N6—C12—H12A | 127.0 |
C7—N4—C9 | 125.7 (7) | C13—C12—H12A | 127.0 |
C11—N5—C13 | 106.1 (9) | C12—C13—N5 | 108.7 (9) |
C11—N5—Cu1 | 129.0 (7) | C12—C13—H13A | 125.6 |
C13—N5—Cu1 | 124.4 (6) | N5—C13—H13A | 125.6 |
C11—N6—C12 | 107.2 (8) | N6—C14—C15 | 113.9 (4) |
C11—N6—C14 | 127.0 (10) | N6—C14—H14A | 108.8 |
C12—N6—C14 | 125.7 (10) | C15—C14—H14A | 108.8 |
C16—N7—C18 | 106.2 (8) | N6—C14—H14B | 108.8 |
C16—N7—Cu1 | 127.6 (6) | C15—C14—H14B | 108.8 |
C18—N7—Cu1 | 126.1 (6) | H14A—C14—H14B | 107.7 |
C16—N8—C17 | 108.5 (8) | C14—C15—H15A | 109.5 |
C16—N8—C19 | 127.3 (8) | C14—C15—H15B | 109.5 |
C17—N8—C19 | 124.1 (8) | H15A—C15—H15B | 109.5 |
N1—C1—N2 | 111.9 (9) | C14—C15—H15C | 109.5 |
N1—C1—H1A | 124.1 | H15A—C15—H15C | 109.5 |
N2—C1—H1A | 124.1 | H15B—C15—H15C | 109.5 |
C3—C2—N2 | 105.3 (9) | N7—C16—N8 | 111.0 (8) |
C3—C2—H2A | 127.4 | N7—C16—H16A | 124.5 |
N2—C2—H2A | 127.4 | N8—C16—H16A | 124.5 |
C2—C3—N1 | 111.7 (4) | N8—C17—C18 | 105.2 (8) |
C2—C3—H3A | 124.2 | N8—C17—H17A | 127.4 |
N1—C3—H3A | 124.2 | C18—C17—H17A | 127.4 |
C5—C4—N2 | 112.1 (11) | N7—C18—C17 | 109.2 (8) |
C5—C4—H4A | 109.2 | N7—C18—H18A | 125.4 |
N2—C4—H4A | 109.2 | C17—C18—H18A | 125.4 |
C5—C4—H4B | 109.2 | N8—C19—C20 | 111.5 (9) |
N2—C4—H4B | 109.2 | N8—C19—H19A | 109.3 |
H4A—C4—H4B | 107.9 | C20—C19—H19A | 109.3 |
C4—C5—H5A | 109.5 | N8—C19—H19B | 109.3 |
C4—C5—H5B | 109.5 | C20—C19—H19B | 109.3 |
H5A—C5—H5B | 109.5 | H19A—C19—H19B | 108.0 |
C4—C5—H5C | 109.5 | C19—C20—H20A | 109.5 |
H5A—C5—H5C | 109.5 | C19—C20—H20B | 109.5 |
H5B—C5—H5C | 109.5 | H20A—C20—H20B | 109.5 |
N3—C6—N4 | 111.4 (8) | C19—C20—H20C | 109.5 |
N3—C6—H6A | 124.3 | H20A—C20—H20C | 109.5 |
N4—C6—H6A | 124.3 | H20B—C20—H20C | 109.5 |
C8—C7—N4 | 105.8 (7) | ||
N3—Cu1—N1—C1 | −51.1 (9) | C2—N2—C4—C5 | 74.7 (17) |
N7—Cu1—N1—C1 | 134.5 (9) | C8—N3—C6—N4 | −0.7 (11) |
Cl1—Cu1—N1—C1 | 43.2 (8) | Cu1—N3—C6—N4 | −171.2 (6) |
N3—Cu1—N1—C3 | 134.9 (8) | C7—N4—C6—N3 | 0.7 (11) |
N7—Cu1—N1—C3 | −39.5 (8) | C9—N4—C6—N3 | 178.8 (8) |
Cl1—Cu1—N1—C3 | −130.8 (8) | C6—N4—C7—C8 | −0.3 (10) |
N1—Cu1—N3—C6 | −90.4 (8) | C9—N4—C7—C8 | −178.4 (8) |
N5—Cu1—N3—C6 | 84.6 (8) | N4—C7—C8—N3 | −0.1 (10) |
Cl1—Cu1—N3—C6 | 176.9 (7) | C6—N3—C8—C7 | 0.5 (11) |
N1—Cu1—N3—C8 | 101.2 (8) | Cu1—N3—C8—C7 | 170.7 (6) |
N5—Cu1—N3—C8 | −83.8 (8) | C6—N4—C9—C10 | 83.2 (14) |
Cl1—Cu1—N3—C8 | 8.5 (8) | C7—N4—C9—C10 | −99.0 (13) |
N3—Cu1—N5—C11 | −55.9 (9) | C13—N5—C11—N6 | −0.7 (12) |
N7—Cu1—N5—C11 | 118.7 (9) | Cu1—N5—C11—N6 | −173.1 (7) |
Cl1—Cu1—N5—C11 | −150.1 (9) | C12—N6—C11—N5 | 1.4 (13) |
N3—Cu1—N5—C13 | 133.0 (8) | C14—N6—C11—N5 | 178.2 (10) |
N7—Cu1—N5—C13 | −52.4 (8) | C11—N6—C12—C13 | −1.4 (12) |
Cl1—Cu1—N5—C13 | 38.8 (8) | C14—N6—C12—C13 | −178.3 (10) |
N1—Cu1—N7—C16 | 131.7 (8) | N6—C12—C13—N5 | 1.0 (12) |
N5—Cu1—N7—C16 | −43.6 (8) | C11—N5—C13—C12 | −0.2 (12) |
Cl1—Cu1—N7—C16 | −135.8 (8) | Cu1—N5—C13—C12 | 172.6 (7) |
N1—Cu1—N7—C18 | −53.5 (8) | C11—N6—C14—C15 | −74 (2) |
N5—Cu1—N7—C18 | 131.2 (8) | C12—N6—C14—C15 | 102.6 (18) |
Cl1—Cu1—N7—C18 | 39.0 (8) | C18—N7—C16—N8 | −0.7 (11) |
C3—N1—C1—N2 | −1.2 (12) | Cu1—N7—C16—N8 | 174.9 (6) |
Cu1—N1—C1—N2 | −176.4 (7) | C17—N8—C16—N7 | 0.3 (11) |
C2—N2—C1—N1 | 2.2 (13) | C19—N8—C16—N7 | −177.5 (8) |
C4—N2—C1—N1 | 178.0 (10) | C16—N8—C17—C18 | 0.2 (11) |
C1—N2—C2—C3 | −2.2 (12) | C19—N8—C17—C18 | 178.2 (9) |
C4—N2—C2—C3 | −178.0 (11) | C16—N7—C18—C17 | 0.9 (11) |
N2—C2—C3—N1 | 1.6 (13) | Cu1—N7—C18—C17 | −174.8 (6) |
C1—N1—C3—C2 | −0.3 (12) | N8—C17—C18—N7 | −0.7 (11) |
Cu1—N1—C3—C2 | 174.7 (8) | C16—N8—C19—C20 | 105.1 (12) |
C1—N2—C4—C5 | −100.3 (16) | C17—N8—C19—C20 | −72.4 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1WA···Cl2i | 0.84 (10) | 2.47 (11) | 3.206 (11) | 147 |
O1W—H1WB···Cl1 | 0.85 (10) | 2.39 (9) | 3.183 (9) | 156 (9) |
C6—H6A···Cl2 | 0.93 | 2.61 | 3.401 (5) | 143 |
C7—H7A···Cl2ii | 0.93 | 2.81 | 3.595 (6) | 143 |
C9—H9B···Cl1iii | 0.97 | 2.72 | 3.598 (9) | 151 |
C11—H11A···O1Wiii | 0.93 | 2.47 | 3.361 (9) | 161 |
C19—H19B···Cl1iv | 0.97 | 2.77 | 3.713 (12) | 162 |
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x, y−1, z; (iii) x+1/2, −y+3/2, z+1/2; (iv) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [CuCl(C5H8N2)4]Cl·H2O |
Mr | 537.00 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 293 |
a, b, c (Å) | 20.304 (4), 8.6090 (17), 17.364 (4) |
β (°) | 119.65 (3) |
V (Å3) | 2637.8 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.06 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.816, 0.902 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5104, 2811, 2013 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.140, 0.95 |
No. of reflections | 2811 |
No. of parameters | 302 |
No. of restraints | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.77, −0.48 |
Absolute structure | Flack (1983), with 212 Friedel pairs |
Absolute structure parameter | 0.09 (3) |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2001) and local programs.
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1WA···Cl2i | 0.84 (10) | 2.47 (11) | 3.206 (11) | 147 |
O1W—H1WB···Cl1 | 0.85 (10) | 2.39 (9) | 3.183 (9) | 156 (9) |
C6—H6A···Cl2 | 0.93 | 2.61 | 3.401 (5) | 143 |
C7—H7A···Cl2ii | 0.93 | 2.81 | 3.595 (6) | 143 |
C9—H9B···Cl1iii | 0.97 | 2.72 | 3.598 (9) | 151 |
C11—H11A···O1Wiii | 0.93 | 2.47 | 3.361 (9) | 161 |
C19—H19B···Cl1iv | 0.97 | 2.77 | 3.713 (12) | 162 |
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x, y−1, z; (iii) x+1/2, −y+3/2, z+1/2; (iv) x, y+1, z. |
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In title compound, the crystal structure consists of discrete CuCl(Eim)4+ cations, Cl- anions and water molecules. The CuII ion adopts a distorted square pyramidal geometry. The basal coordination positions are occupied by the N atoms of the Eim ligands with bond lengths ranging from 1.960 (7) to 2.075 (8) Å, and the apical position by a Cl anion [Cu—Cl = 2.730 (3) Å], while another chloride anion in the general position balances the charges. All these values agree well with two polymorphism complexes [CuCl(im)4Cl](im is 1H-imidazole) (Otieno et al., 2001; Jian et al., 2004). In the crystal, the title compound form three-dimensional hydrogen bond networks to stabilize the structure.