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In the crystal structure of the title complex, [CuII(C3H6NS2)Cl(C12H8N2)], the CuII atom has a distorted square-pyramidal coordination geometry comprising one S,S′-bidentate dimethyl­dithio­carbamate (Me2dtc) 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 Csp2—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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602263X/ym2006sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680602263X/ym2006Isup2.hkl
Contains datablock I

CCDC reference: 613871

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](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

Computing details top

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 = 399.43Dx = 1.645 Mg m3
Orthorhombic, CmcaMo Kα radiation, λ = 0.7107 Å
Hall symbol: -C 2bc 2Cell parameters from 12643 reflections
a = 13.98 (2) Åθ = 3.0–27.5°
b = 13.45 (1) ŵ = 1.78 mm1
c = 17.15 (2) ÅT = 296 K
V = 3225 (6) Å3Prism, black
Z = 80.20 × 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-1Rint = 0.018
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1818
Tmin = 0.615, Tmax = 0.837k = 1717
16013 measured reflectionsl = 2122
1934 independent reflections
Refinement top
Refinement on F2H-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 = 1.13Δρmax = 0.45 e Å3
1934 reflectionsΔρmin = 0.27 e Å3
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
xyzUiso*/Ueq
Cu10.00000.15737 (2)0.40484 (2)0.0377 (1)
Cl10.00000.34078 (4)0.42243 (4)0.0425 (2)
S10.10252 (4)0.13292 (4)0.30103 (3)0.0471 (1)
N10.0948 (1)0.1324 (1)0.49358 (9)0.0378 (3)
N20.00000.1040 (2)0.1708 (1)0.0446 (5)
C10.1892 (1)0.1315 (1)0.4920 (1)0.0493 (5)
C20.2452 (2)0.1301 (2)0.5593 (2)0.0607 (6)
C30.2018 (2)0.1298 (1)0.6298 (1)0.0606 (6)
C40.1017 (1)0.1296 (1)0.6350 (1)0.0447 (4)
C50.0511 (1)0.1302 (1)0.5644 (1)0.0363 (4)
C60.00000.1206 (2)0.2469 (1)0.0396 (5)
C70.0891 (2)0.0926 (2)0.1276 (1)0.0570 (5)
C80.0483 (2)0.1293 (1)0.7061 (1)0.0537 (5)
H10.21970.13180.44380.059*
H20.31160.12950.55570.073*
H30.23860.12960.67500.073*
H7A0.07510.08000.07370.085*
H7B0.12480.03790.14870.085*
H7C0.12610.15250.13200.085*
H80.08090.12920.75340.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0326 (2)0.0473 (2)0.0332 (2)0.00000.00000.0023 (1)
Cl10.0359 (4)0.0429 (3)0.0488 (4)0.00000.00000.0014 (2)
S10.0393 (3)0.0609 (3)0.0411 (3)0.0023 (2)0.0008 (2)0.0021 (2)
N10.0308 (8)0.0423 (7)0.0402 (8)0.0020 (6)0.0004 (6)0.0054 (6)
N20.048 (1)0.047 (1)0.039 (1)0.00000.00000.0036 (9)
C10.034 (1)0.058 (1)0.056 (1)0.0029 (8)0.0019 (9)0.0103 (9)
C20.033 (1)0.072 (1)0.077 (2)0.001 (1)0.012 (1)0.017 (1)
C30.053 (1)0.069 (1)0.060 (1)0.004 (1)0.025 (1)0.011 (1)
C40.049 (1)0.0416 (8)0.043 (1)0.0020 (8)0.0114 (8)0.0063 (8)
C50.038 (1)0.0343 (7)0.0371 (9)0.0004 (7)0.0031 (7)0.0035 (7)
C60.041 (1)0.039 (1)0.039 (1)0.00000.00000.001 (1)
C70.065 (1)0.060 (1)0.046 (1)0.001 (1)0.012 (1)0.0084 (9)
C80.075 (2)0.050 (1)0.036 (1)0.002 (1)0.0092 (9)0.0007 (8)
Geometric parameters (Å, º) top
Cu1—Cl12.485 (4)C2—C31.353 (4)
Cu1—S12.309 (3)C2—H20.9300
Cu1—S12.309 (3)C3—C41.402 (3)
Cu1—N12.045 (2)C3—H30.9299
Cu1—N12.045 (2)C4—C51.404 (3)
S1—C61.716 (3)C4—C81.429 (3)
N1—C11.321 (3)C5—C51.428 (3)
N1—C51.359 (2)C6—S11.716 (3)
N2—C61.325 (3)C7—H7A0.9601
N2—C71.457 (3)C7—H7B0.9599
N2—C71.457 (3)C7—H7C0.9599
C1—C21.395 (3)C8—C81.352 (4)
C1—H10.9301C8—H80.9299
Cu1···C13.058 (5)C4···C82.426 (3)
Cu1···C13.058 (5)C4···H23.2341
Cu1···C52.851 (2)C4···H32.0316
Cu1···C52.851 (2)C4···H7C2.9515
Cu1···C62.753 (2)C4···H82.0511
Cu1···H13.1619C4···H83.2615
Cu1···H13.1619C5···N12.373 (2)
Cl1···N13.332 (5)C5···C13.581 (3)
Cl1···N13.332 (5)C5···C42.456 (3)
Cl1···C23.597 (2)C5···C82.431 (3)
Cl1···C23.597 (2)C5···C82.800 (3)
Cl1···H22.6901C5···H13.1364
Cl1···H22.6901C5···H33.2351
Cl1···H7A2.9944C5···H7C3.3148
Cl1···H7A2.9944C5···H83.2687
Cl1···H7A3.3851C6···C72.425 (3)
Cl1···H7A3.3851C6···C72.425 (3)
Cl1···H7B3.3998C6···C83.501 (3)
Cl1···H7B3.3998C6···C83.501 (3)
Cl1···H83.1371C6···C83.522 (3)
Cl1···H83.1371C6···C83.522 (3)
S1···S12.8663 (8)C6···H7A3.1973
S1···N13.304 (5)C6···H7A3.1973
S1···N22.682 (2)C6···H7B2.6678
S1···C13.492 (5)C6···H7B2.6678
S1···C73.029 (5)C6···H7C2.6788
S1···H12.9456C6···H7C2.6788
S1···H7B2.9249C6···H83.5520
S1···H7C2.9294C6···H83.5520
S1···H83.3161C6···H83.5446
N1···N12.649 (2)C6···H83.5446
N1···N13.569 (2)C7···C72.491 (3)
N1···C22.386 (3)C7···H12.9863
N1···C32.774 (3)C7···H23.5170
N1···C42.428 (3)C7···H23.4717
N1···C52.373 (2)C7···H7A2.4807
N1···H11.9448C7···H7B3.1006
N1···H23.2135C7···H7C3.1156
N1···H23.5614C8···C42.426 (3)
N2···S12.682 (2)C8···C52.800 (3)
N2···H7A1.9943C8···C63.501 (3)
N2···H7A1.9943C8···C63.522 (3)
N2···H7B1.9941C8···H32.7122
N2···H7B1.9941C8···H7B3.5214
N2···H7C1.9942C8···H7C3.3780
N2···H7C1.9942C8···H81.9801
N2···H83.5779H1···C23.5418
N2···H83.5779H1···C23.2392
C1···C13.549 (3)H1···C72.9863
C1···C23.448 (3)H2···Cl12.6901
C1···C32.370 (3)H2···N13.5614
C1···C42.742 (3)H2···C13.3167
C1···C52.296 (3)H2···C73.5170
C1···C53.581 (3)H2···C73.4717
C1···H22.0308H3···C33.4514
C1···H23.3167H7A···Cl12.9944
C1···H33.2133H7A···Cl13.3851
C1···H7A3.5501H7A···C13.5501
C1···H7C3.3557H7A···C23.4583
C2···Cl13.597 (2)H7A···C72.4807
C2···C13.448 (3)H7B···Cl13.3998
C2···C42.390 (3)H7B···C23.2804
C2···C52.716 (3)H7B···C33.3266
C2···H12.0125H7B···C73.1006
C2···H13.5418H7B···C83.5214
C2···H13.2392H7C···C13.3557
C2···H31.9863H7C···C23.5885
C2···H7A3.4583H7C···C33.1143
C2···H7B3.2804H7C···C42.9515
C2···H7C3.5885H7C···C53.3148
C3···C52.387 (3)H7C···C73.1156
C3···C82.513 (3)H7C···C83.3780
C3···H13.1995H8···Cl13.1371
C3···H21.9921H8···S13.3161
C3···H33.4514H8···N23.5779
C3···H7B3.3266H8···C43.2615
C3···H7C3.1143H8···C63.5520
C3···H82.7123H8···C63.5446
C4···C42.844 (3)H8···C81.9801
C4···C52.456 (3)
Cl1—Cu1—S1103.59 (2)C3—C2—H2120.4088
Cl1—Cu1—S1103.59 (2)H2—C2—C1120.4139
Cl1—Cu1—N194.16 (4)C4—C3—C2120.4 (2)
Cl1—Cu1—N194.16 (4)C4—C3—H3119.8324
S1—Cu1—S176.73 (2)H3—C3—C2119.8052
S1—Cu1—N198.54 (5)C5—C4—C3116.6 (2)
S1—Cu1—N1162.23 (5)C5—C4—C8118.2 (2)
S1—Cu1—N1162.23 (5)C8—C4—C3125.2 (2)
S1—Cu1—N198.54 (5)C5—C5—N1116.7 (2)
N1—Cu1—N180.72 (6)C5—C5—C4120.3 (2)
C6—S1—Cu184.98 (7)S1—C6—S1113.3 (1)
C1—N1—Cu1129.3 (1)S1—C6—N2123.34 (7)
C1—N1—C5117.9 (2)H7A—C7—N2109.4742
C5—N1—Cu1112.2 (1)H7A—C7—H7B109.4667
C6—N2—C7121.2 (1)H7A—C7—H7C109.4744
C6—N2—C7121.2 (1)H7B—C7—N2109.4631
C7—N2—C7117.5 (2)H7B—C7—H7C109.4783
C2—C1—N1122.9 (2)H7C—C7—N2109.4706
C2—C1—H1118.5311C8—C8—C4121.5 (2)
H1—C1—N1118.5222C8—C8—H8119.2559
C3—C2—C1119.2 (2)H8—C8—C4119.2698
Cl1—Cu1—S1—C6100.84 (9)C6—N2—C7—H7A179.1
Cl1—Cu1—N1—C187.44 (13)N1—C1—C2—C30.1 (2)
Cu1—S1—C6—N2179.3 (2)C1—C2—C3—C40.8 (3)
Cu1—N1—C1—C2168.8 (2)C2—C3—C4—C50.3 (3)
Cu1—N1—C5—C4169.9 (1)C3—C4—C5—N11.0 (3)
C7—N2—C6—S11.4 (6)C3—C4—C8—H80.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Cl1i0.932.693.597 (5)165
Symmetry code: (i) x+1/2, y+1/2, z+1.
 

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