In the crystal structure of the title complex, [Cu
II(C
3H
6NS
2)Cl(C
12H
8N
2)], the Cu
II atom has a distorted square-pyramidal coordination geometry comprising one
S,
S′-bidentate dimethyldithiocarbamate (Me
2dtc) ligand, one
N,
N′-bidentate 1,10-phenanthroline (phen) ligand and an apical Cl atom. A mirror plane passes through the Cu and Cl atoms, and also through the C
sp2—N bond of the dithiocarbamate. The complex molecules are linked together by C—H
Cl hydrogen bonds, forming a bilayered one-dimensional chain along the
a axis.
Supporting information
CCDC reference: 613871
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.026
- wR factor = 0.083
- Data-to-parameter ratio = 18.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu1 - Cl1 .. 12.49 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu1 - S1 .. 13.54 su
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.615 0.837
Tmin(prime) and Tmax expected: 0.697 0.837
RR(prime) = 0.882
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.88
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
2 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
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2005) and CRYSTALS (Watkin et al., 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CrystalStructure.
Chloro(
N,
N'-dimethyldithiocarbamato-
κ2S,
S')(1,10-phenanthroline-
κ2N,
N')copper(II)
top
Crystal data top
[Cu(C3H6NS2)Cl(C12H8N2)] | F(000) = 1624.00 |
Mr = 399.43 | Dx = 1.645 Mg m−3 |
Orthorhombic, Cmca | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -C 2bc 2 | Cell parameters from 12643 reflections |
a = 13.98 (2) Å | θ = 3.0–27.5° |
b = 13.45 (1) Å | µ = 1.78 mm−1 |
c = 17.15 (2) Å | T = 296 K |
V = 3225 (6) Å3 | Prism, black |
Z = 8 | 0.20 × 0.10 × 0.10 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 1430 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.018 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −18→18 |
Tmin = 0.615, Tmax = 0.837 | k = −17→17 |
16013 measured reflections | l = −21→22 |
1934 independent reflections | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.026 | w = 1/[σ2(Fo2) + (0.0536P)2 + 0.1587P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.083 | (Δ/σ)max < 0.001 |
S = 1.13 | Δρmax = 0.45 e Å−3 |
1934 reflections | Δρmin = −0.27 e Å−3 |
107 parameters | |
Special details top
Refinement. Refinement using all reflections. The weighted R-factor (wR),
goodness of fit (S) and R-factor (gt) are based on F,
with F set to zero for negative F. The threshold expression of
F2 > 2.0 σ(F2) is used only for calculating R-factor
(gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.0000 | 0.15737 (2) | 0.40484 (2) | 0.0377 (1) | |
Cl1 | 0.0000 | 0.34078 (4) | 0.42243 (4) | 0.0425 (2) | |
S1 | 0.10252 (4) | 0.13292 (4) | 0.30103 (3) | 0.0471 (1) | |
N1 | 0.0948 (1) | 0.1324 (1) | 0.49358 (9) | 0.0378 (3) | |
N2 | 0.0000 | 0.1040 (2) | 0.1708 (1) | 0.0446 (5) | |
C1 | 0.1892 (1) | 0.1315 (1) | 0.4920 (1) | 0.0493 (5) | |
C2 | 0.2452 (2) | 0.1301 (2) | 0.5593 (2) | 0.0607 (6) | |
C3 | 0.2018 (2) | 0.1298 (1) | 0.6298 (1) | 0.0606 (6) | |
C4 | 0.1017 (1) | 0.1296 (1) | 0.6350 (1) | 0.0447 (4) | |
C5 | 0.0511 (1) | 0.1302 (1) | 0.5644 (1) | 0.0363 (4) | |
C6 | 0.0000 | 0.1206 (2) | 0.2469 (1) | 0.0396 (5) | |
C7 | 0.0891 (2) | 0.0926 (2) | 0.1276 (1) | 0.0570 (5) | |
C8 | 0.0483 (2) | 0.1293 (1) | 0.7061 (1) | 0.0537 (5) | |
H1 | 0.2197 | 0.1318 | 0.4438 | 0.059* | |
H2 | 0.3116 | 0.1295 | 0.5557 | 0.073* | |
H3 | 0.2386 | 0.1296 | 0.6750 | 0.073* | |
H7A | 0.0751 | 0.0800 | 0.0737 | 0.085* | |
H7B | 0.1248 | 0.0379 | 0.1487 | 0.085* | |
H7C | 0.1261 | 0.1525 | 0.1320 | 0.085* | |
H8 | 0.0809 | 0.1292 | 0.7534 | 0.064* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0326 (2) | 0.0473 (2) | 0.0332 (2) | 0.0000 | 0.0000 | 0.0023 (1) |
Cl1 | 0.0359 (4) | 0.0429 (3) | 0.0488 (4) | 0.0000 | 0.0000 | −0.0014 (2) |
S1 | 0.0393 (3) | 0.0609 (3) | 0.0411 (3) | 0.0023 (2) | 0.0008 (2) | −0.0021 (2) |
N1 | 0.0308 (8) | 0.0423 (7) | 0.0402 (8) | 0.0020 (6) | 0.0004 (6) | 0.0054 (6) |
N2 | 0.048 (1) | 0.047 (1) | 0.039 (1) | 0.0000 | 0.0000 | −0.0036 (9) |
C1 | 0.034 (1) | 0.058 (1) | 0.056 (1) | 0.0029 (8) | 0.0019 (9) | 0.0103 (9) |
C2 | 0.033 (1) | 0.072 (1) | 0.077 (2) | −0.001 (1) | −0.012 (1) | 0.017 (1) |
C3 | 0.053 (1) | 0.069 (1) | 0.060 (1) | −0.004 (1) | −0.025 (1) | 0.011 (1) |
C4 | 0.049 (1) | 0.0416 (8) | 0.043 (1) | −0.0020 (8) | −0.0114 (8) | 0.0063 (8) |
C5 | 0.038 (1) | 0.0343 (7) | 0.0371 (9) | −0.0004 (7) | −0.0031 (7) | 0.0035 (7) |
C6 | 0.041 (1) | 0.039 (1) | 0.039 (1) | 0.0000 | 0.0000 | 0.001 (1) |
C7 | 0.065 (1) | 0.060 (1) | 0.046 (1) | 0.001 (1) | 0.012 (1) | −0.0084 (9) |
C8 | 0.075 (2) | 0.050 (1) | 0.036 (1) | −0.002 (1) | −0.0092 (9) | −0.0007 (8) |
Geometric parameters (Å, º) top
Cu1—Cl1 | 2.485 (4) | C2—C3 | 1.353 (4) |
Cu1—S1 | 2.309 (3) | C2—H2 | 0.9300 |
Cu1—S1 | 2.309 (3) | C3—C4 | 1.402 (3) |
Cu1—N1 | 2.045 (2) | C3—H3 | 0.9299 |
Cu1—N1 | 2.045 (2) | C4—C5 | 1.404 (3) |
S1—C6 | 1.716 (3) | C4—C8 | 1.429 (3) |
N1—C1 | 1.321 (3) | C5—C5 | 1.428 (3) |
N1—C5 | 1.359 (2) | C6—S1 | 1.716 (3) |
N2—C6 | 1.325 (3) | C7—H7A | 0.9601 |
N2—C7 | 1.457 (3) | C7—H7B | 0.9599 |
N2—C7 | 1.457 (3) | C7—H7C | 0.9599 |
C1—C2 | 1.395 (3) | C8—C8 | 1.352 (4) |
C1—H1 | 0.9301 | C8—H8 | 0.9299 |
| | | |
Cu1···C1 | 3.058 (5) | C4···C8 | 2.426 (3) |
Cu1···C1 | 3.058 (5) | C4···H2 | 3.2341 |
Cu1···C5 | 2.851 (2) | C4···H3 | 2.0316 |
Cu1···C5 | 2.851 (2) | C4···H7C | 2.9515 |
Cu1···C6 | 2.753 (2) | C4···H8 | 2.0511 |
Cu1···H1 | 3.1619 | C4···H8 | 3.2615 |
Cu1···H1 | 3.1619 | C5···N1 | 2.373 (2) |
Cl1···N1 | 3.332 (5) | C5···C1 | 3.581 (3) |
Cl1···N1 | 3.332 (5) | C5···C4 | 2.456 (3) |
Cl1···C2 | 3.597 (2) | C5···C8 | 2.431 (3) |
Cl1···C2 | 3.597 (2) | C5···C8 | 2.800 (3) |
Cl1···H2 | 2.6901 | C5···H1 | 3.1364 |
Cl1···H2 | 2.6901 | C5···H3 | 3.2351 |
Cl1···H7A | 2.9944 | C5···H7C | 3.3148 |
Cl1···H7A | 2.9944 | C5···H8 | 3.2687 |
Cl1···H7A | 3.3851 | C6···C7 | 2.425 (3) |
Cl1···H7A | 3.3851 | C6···C7 | 2.425 (3) |
Cl1···H7B | 3.3998 | C6···C8 | 3.501 (3) |
Cl1···H7B | 3.3998 | C6···C8 | 3.501 (3) |
Cl1···H8 | 3.1371 | C6···C8 | 3.522 (3) |
Cl1···H8 | 3.1371 | C6···C8 | 3.522 (3) |
S1···S1 | 2.8663 (8) | C6···H7A | 3.1973 |
S1···N1 | 3.304 (5) | C6···H7A | 3.1973 |
S1···N2 | 2.682 (2) | C6···H7B | 2.6678 |
S1···C1 | 3.492 (5) | C6···H7B | 2.6678 |
S1···C7 | 3.029 (5) | C6···H7C | 2.6788 |
S1···H1 | 2.9456 | C6···H7C | 2.6788 |
S1···H7B | 2.9249 | C6···H8 | 3.5520 |
S1···H7C | 2.9294 | C6···H8 | 3.5520 |
S1···H8 | 3.3161 | C6···H8 | 3.5446 |
N1···N1 | 2.649 (2) | C6···H8 | 3.5446 |
N1···N1 | 3.569 (2) | C7···C7 | 2.491 (3) |
N1···C2 | 2.386 (3) | C7···H1 | 2.9863 |
N1···C3 | 2.774 (3) | C7···H2 | 3.5170 |
N1···C4 | 2.428 (3) | C7···H2 | 3.4717 |
N1···C5 | 2.373 (2) | C7···H7A | 2.4807 |
N1···H1 | 1.9448 | C7···H7B | 3.1006 |
N1···H2 | 3.2135 | C7···H7C | 3.1156 |
N1···H2 | 3.5614 | C8···C4 | 2.426 (3) |
N2···S1 | 2.682 (2) | C8···C5 | 2.800 (3) |
N2···H7A | 1.9943 | C8···C6 | 3.501 (3) |
N2···H7A | 1.9943 | C8···C6 | 3.522 (3) |
N2···H7B | 1.9941 | C8···H3 | 2.7122 |
N2···H7B | 1.9941 | C8···H7B | 3.5214 |
N2···H7C | 1.9942 | C8···H7C | 3.3780 |
N2···H7C | 1.9942 | C8···H8 | 1.9801 |
N2···H8 | 3.5779 | H1···C2 | 3.5418 |
N2···H8 | 3.5779 | H1···C2 | 3.2392 |
C1···C1 | 3.549 (3) | H1···C7 | 2.9863 |
C1···C2 | 3.448 (3) | H2···Cl1 | 2.6901 |
C1···C3 | 2.370 (3) | H2···N1 | 3.5614 |
C1···C4 | 2.742 (3) | H2···C1 | 3.3167 |
C1···C5 | 2.296 (3) | H2···C7 | 3.5170 |
C1···C5 | 3.581 (3) | H2···C7 | 3.4717 |
C1···H2 | 2.0308 | H3···C3 | 3.4514 |
C1···H2 | 3.3167 | H7A···Cl1 | 2.9944 |
C1···H3 | 3.2133 | H7A···Cl1 | 3.3851 |
C1···H7A | 3.5501 | H7A···C1 | 3.5501 |
C1···H7C | 3.3557 | H7A···C2 | 3.4583 |
C2···Cl1 | 3.597 (2) | H7A···C7 | 2.4807 |
C2···C1 | 3.448 (3) | H7B···Cl1 | 3.3998 |
C2···C4 | 2.390 (3) | H7B···C2 | 3.2804 |
C2···C5 | 2.716 (3) | H7B···C3 | 3.3266 |
C2···H1 | 2.0125 | H7B···C7 | 3.1006 |
C2···H1 | 3.5418 | H7B···C8 | 3.5214 |
C2···H1 | 3.2392 | H7C···C1 | 3.3557 |
C2···H3 | 1.9863 | H7C···C2 | 3.5885 |
C2···H7A | 3.4583 | H7C···C3 | 3.1143 |
C2···H7B | 3.2804 | H7C···C4 | 2.9515 |
C2···H7C | 3.5885 | H7C···C5 | 3.3148 |
C3···C5 | 2.387 (3) | H7C···C7 | 3.1156 |
C3···C8 | 2.513 (3) | H7C···C8 | 3.3780 |
C3···H1 | 3.1995 | H8···Cl1 | 3.1371 |
C3···H2 | 1.9921 | H8···S1 | 3.3161 |
C3···H3 | 3.4514 | H8···N2 | 3.5779 |
C3···H7B | 3.3266 | H8···C4 | 3.2615 |
C3···H7C | 3.1143 | H8···C6 | 3.5520 |
C3···H8 | 2.7123 | H8···C6 | 3.5446 |
C4···C4 | 2.844 (3) | H8···C8 | 1.9801 |
C4···C5 | 2.456 (3) | | |
| | | |
Cl1—Cu1—S1 | 103.59 (2) | C3—C2—H2 | 120.4088 |
Cl1—Cu1—S1 | 103.59 (2) | H2—C2—C1 | 120.4139 |
Cl1—Cu1—N1 | 94.16 (4) | C4—C3—C2 | 120.4 (2) |
Cl1—Cu1—N1 | 94.16 (4) | C4—C3—H3 | 119.8324 |
S1—Cu1—S1 | 76.73 (2) | H3—C3—C2 | 119.8052 |
S1—Cu1—N1 | 98.54 (5) | C5—C4—C3 | 116.6 (2) |
S1—Cu1—N1 | 162.23 (5) | C5—C4—C8 | 118.2 (2) |
S1—Cu1—N1 | 162.23 (5) | C8—C4—C3 | 125.2 (2) |
S1—Cu1—N1 | 98.54 (5) | C5—C5—N1 | 116.7 (2) |
N1—Cu1—N1 | 80.72 (6) | C5—C5—C4 | 120.3 (2) |
C6—S1—Cu1 | 84.98 (7) | S1—C6—S1 | 113.3 (1) |
C1—N1—Cu1 | 129.3 (1) | S1—C6—N2 | 123.34 (7) |
C1—N1—C5 | 117.9 (2) | H7A—C7—N2 | 109.4742 |
C5—N1—Cu1 | 112.2 (1) | H7A—C7—H7B | 109.4667 |
C6—N2—C7 | 121.2 (1) | H7A—C7—H7C | 109.4744 |
C6—N2—C7 | 121.2 (1) | H7B—C7—N2 | 109.4631 |
C7—N2—C7 | 117.5 (2) | H7B—C7—H7C | 109.4783 |
C2—C1—N1 | 122.9 (2) | H7C—C7—N2 | 109.4706 |
C2—C1—H1 | 118.5311 | C8—C8—C4 | 121.5 (2) |
H1—C1—N1 | 118.5222 | C8—C8—H8 | 119.2559 |
C3—C2—C1 | 119.2 (2) | H8—C8—C4 | 119.2698 |
| | | |
Cl1—Cu1—S1—C6 | −100.84 (9) | C6—N2—C7—H7A | 179.1 |
Cl1—Cu1—N1—C1 | −87.44 (13) | N1—C1—C2—C3 | −0.1 (2) |
Cu1—S1—C6—N2 | 179.3 (2) | C1—C2—C3—C4 | 0.8 (3) |
Cu1—N1—C1—C2 | 168.8 (2) | C2—C3—C4—C5 | −0.3 (3) |
Cu1—N1—C5—C4 | −169.9 (1) | C3—C4—C5—N1 | −1.0 (3) |
C7—N2—C6—S1 | 1.4 (6) | C3—C4—C8—H8 | −0.1 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cl1i | 0.93 | 2.69 | 3.597 (5) | 165 |
Symmetry code: (i) −x+1/2, −y+1/2, −z+1. |