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Mol­ecules of the title dinuclear complex, [Cu2(C9H9O2S)4(C3H7NO)2], lie on centers of inversion located midway between the Cu atoms. Four carboxyl­ate anions function as bridges to the two Cu atoms and each Cu atom is coordinated by an N,N′-dimethyl­formamide mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013602/ci2025sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013602/ci2025Isup2.hkl
Contains datablock I

CCDC reference: 291530

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.049
  • wR factor = 0.140
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N1
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.00 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.23 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13' PLAT301_ALERT_3_C Main Residue Disorder ......................... 19.00 Perc. PLAT320_ALERT_2_C Check Hybridisation of C19 in Main Residue . ? PLAT320_ALERT_2_C Check Hybridisation of C20 in Main Residue . ? PLAT320_ALERT_2_C Check Hybridisation of C21 in Main Residue . ? PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C16'
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

Tetrakis(µ-4-tolylsulfanylacetato-κ2O:O')bis[(N,N'- dimethylformamide-κO)copper(II)] top
Crystal data top
[Cu2(C9H9O2S)4(C3H7NO)2]F(000) = 1008
Mr = 984.11Dx = 1.418 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2295 reflections
a = 10.997 (7) Åθ = 1.9–27.8°
b = 7.808 (5) ŵ = 1.16 mm1
c = 27.066 (17) ÅT = 273 K
β = 97.49 (1)°Prism, green
V = 2304 (3) Å30.30 × 0.20 × 0.18 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
5397 independent reflections
Radiation source: fine-focus sealed tube3383 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
φ and ω scansθmax = 27.8°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.757, Tmax = 0.812k = 710
14547 measured reflectionsl = 3335
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0643P)2]
where P = (Fo2 + 2Fc2)/3
5397 reflections(Δ/σ)max = 0.001
338 parametersΔρmax = 0.89 e Å3
38 restraintsΔρmin = 0.47 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.39525 (3)0.42264 (5)0.004521 (13)0.04032 (15)
S10.41150 (10)0.60759 (15)0.18109 (3)0.0653 (3)
S20.80652 (8)0.09866 (15)0.09115 (4)0.0639 (3)
O10.4223 (2)0.4924 (3)0.07471 (8)0.0535 (6)
O20.5966 (2)0.6278 (3)0.06643 (8)0.0556 (7)
O30.49371 (19)0.2181 (3)0.02382 (8)0.0505 (6)
O40.66980 (19)0.3492 (3)0.01476 (9)0.0564 (6)
O50.21435 (19)0.3166 (3)0.00251 (9)0.0537 (6)
C10.3355 (3)0.8035 (5)0.16511 (12)0.0538 (9)
C20.3474 (3)0.8982 (5)0.12321 (13)0.0581 (10)
H20.39680.85800.10030.070*
C30.2877 (4)1.0498 (6)0.11483 (14)0.0644 (11)
H30.29921.11270.08660.077*
C40.2096 (3)1.1145 (6)0.14721 (17)0.0686 (12)
C50.1948 (4)1.0144 (7)0.18830 (15)0.0725 (12)
H50.14061.05030.20990.087*
C60.2568 (4)0.8659 (6)0.19795 (14)0.0661 (11)
H60.24720.80430.22660.079*
C70.1466 (4)1.2851 (7)0.13740 (19)0.0923 (15)
H7A0.15841.35330.16720.138*
H7B0.06051.26710.12760.138*
H7C0.18091.34340.11120.138*
C80.5394 (3)0.6158 (5)0.14677 (12)0.0559 (10)
H8A0.57430.72980.15050.067*
H8B0.60100.53660.16210.067*
C90.5156 (3)0.5749 (4)0.09122 (11)0.0444 (8)
C100.7332 (14)0.0863 (16)0.1437 (6)0.056 (4)0.485 (4)
C110.6145 (15)0.144 (3)0.1491 (7)0.063 (7)0.485 (4)
H11A0.56710.19800.12260.075*0.485 (4)
C120.5680 (19)0.122 (2)0.1942 (5)0.061 (5)0.485 (4)
H12A0.48960.16090.19750.074*0.485 (4)
C130.6377 (9)0.0414 (13)0.2343 (3)0.081 (3)0.485 (4)
C140.7552 (9)0.0160 (13)0.2286 (3)0.090 (3)0.485 (4)
H14A0.80240.06920.25520.108*0.485 (4)
C150.8033 (8)0.0044 (13)0.1840 (3)0.073 (3)0.485 (4)
H15A0.88150.03590.18080.088*0.485 (4)
C160.5839 (14)0.0154 (18)0.2815 (4)0.130 (5)0.485 (4)
H16A0.64570.03480.30940.194*0.485 (4)
H16B0.55390.09970.28270.194*0.485 (4)
H16C0.51750.09440.28280.194*0.485 (4)
C10'0.7411 (11)0.1490 (15)0.1468 (5)0.048 (3)0.515 (4)
C11'0.6194 (13)0.126 (2)0.1508 (6)0.061 (7)0.515 (4)
H11B0.56610.08510.12390.073*0.515 (4)
C12'0.5774 (17)0.162 (2)0.1946 (5)0.068 (5)0.515 (4)
H12B0.49450.14350.19630.081*0.515 (4)
C13'0.6465 (7)0.2228 (11)0.2363 (3)0.066 (2)0.515 (4)
C14'0.7656 (7)0.2511 (12)0.2304 (3)0.082 (3)0.515 (4)
H14B0.81750.29640.25710.098*0.515 (4)
C15'0.8129 (7)0.2164 (11)0.1873 (2)0.069 (2)0.515 (4)
H15B0.89520.23890.18540.083*0.515 (4)
C16'0.5933 (10)0.2486 (16)0.2850 (3)0.108 (4)0.515 (4)
H16D0.63570.17620.31020.162*0.515 (4)
H16E0.50770.21970.28020.162*0.515 (4)
H16F0.60290.36620.29510.162*0.515 (4)
C170.6790 (3)0.0642 (4)0.04372 (13)0.0500 (8)
H17A0.70890.01060.01530.060*
H17B0.62280.01550.05640.060*
C180.6092 (3)0.2232 (5)0.02619 (11)0.0434 (8)
C190.1459 (3)0.3317 (5)0.03853 (16)0.0651 (11)
C200.0457 (5)0.2992 (10)0.0940 (2)0.128 (2)
C210.0325 (5)0.2335 (8)0.0037 (2)0.115 (2)
N10.0293 (2)0.2963 (4)0.04461 (11)0.0547 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0293 (2)0.0547 (3)0.0372 (2)0.00246 (18)0.00495 (14)0.00662 (18)
S10.0739 (7)0.0848 (8)0.0405 (5)0.0005 (5)0.0195 (5)0.0023 (5)
S20.0398 (5)0.0858 (8)0.0642 (6)0.0034 (5)0.0002 (4)0.0076 (5)
O10.0496 (13)0.0703 (17)0.0419 (13)0.0104 (13)0.0108 (11)0.0135 (12)
O20.0439 (13)0.0832 (19)0.0399 (13)0.0113 (12)0.0068 (10)0.0138 (12)
O30.0355 (11)0.0569 (16)0.0583 (15)0.0030 (11)0.0033 (10)0.0061 (11)
O40.0383 (12)0.0581 (16)0.0739 (17)0.0026 (12)0.0116 (12)0.0089 (13)
O50.0343 (11)0.0722 (17)0.0533 (15)0.0079 (12)0.0012 (10)0.0022 (12)
C10.0475 (19)0.077 (3)0.0379 (19)0.0096 (18)0.0077 (15)0.0151 (17)
C20.051 (2)0.081 (3)0.045 (2)0.002 (2)0.0128 (16)0.0107 (19)
C30.057 (2)0.085 (3)0.053 (2)0.001 (2)0.0134 (18)0.004 (2)
C40.047 (2)0.085 (3)0.071 (3)0.002 (2)0.0041 (19)0.023 (2)
C50.062 (2)0.103 (4)0.056 (2)0.000 (3)0.022 (2)0.026 (2)
C60.068 (2)0.090 (3)0.044 (2)0.000 (2)0.0199 (18)0.009 (2)
C70.076 (3)0.104 (4)0.096 (4)0.011 (3)0.009 (3)0.017 (3)
C80.0482 (18)0.078 (3)0.0405 (19)0.0010 (18)0.0037 (15)0.0102 (17)
C90.0409 (17)0.055 (2)0.0373 (17)0.0080 (17)0.0048 (14)0.0072 (15)
C100.055 (6)0.053 (8)0.053 (6)0.022 (6)0.021 (4)0.000 (6)
C110.043 (10)0.055 (9)0.090 (15)0.009 (8)0.009 (8)0.008 (9)
C120.071 (9)0.076 (10)0.039 (7)0.028 (7)0.010 (6)0.001 (5)
C130.104 (8)0.074 (8)0.065 (6)0.015 (6)0.009 (6)0.008 (5)
C140.144 (10)0.078 (7)0.044 (5)0.007 (7)0.003 (6)0.015 (5)
C150.068 (5)0.080 (7)0.065 (6)0.009 (5)0.015 (4)0.013 (5)
C160.217 (15)0.129 (11)0.049 (6)0.045 (11)0.039 (8)0.002 (6)
C10'0.037 (5)0.057 (8)0.048 (5)0.009 (5)0.003 (3)0.002 (5)
C11'0.069 (14)0.080 (12)0.030 (7)0.009 (9)0.011 (7)0.001 (7)
C12'0.049 (7)0.071 (9)0.083 (11)0.009 (7)0.006 (7)0.007 (6)
C13'0.077 (5)0.073 (6)0.047 (4)0.004 (4)0.004 (4)0.004 (4)
C14'0.079 (6)0.107 (8)0.052 (5)0.015 (5)0.021 (4)0.009 (5)
C15'0.050 (4)0.100 (7)0.053 (5)0.012 (4)0.005 (3)0.002 (4)
C16'0.129 (9)0.141 (10)0.057 (6)0.011 (8)0.027 (6)0.018 (6)
C170.0449 (18)0.050 (2)0.054 (2)0.0010 (16)0.0035 (15)0.0074 (16)
C180.0435 (17)0.052 (2)0.0342 (17)0.0001 (16)0.0042 (13)0.0109 (15)
C190.045 (2)0.064 (3)0.084 (3)0.004 (2)0.0010 (19)0.007 (2)
C200.083 (3)0.165 (6)0.120 (5)0.006 (4)0.047 (3)0.016 (4)
C210.077 (3)0.155 (6)0.121 (5)0.035 (3)0.048 (3)0.004 (4)
N10.0316 (13)0.064 (2)0.068 (2)0.0002 (14)0.0069 (13)0.0040 (16)
Geometric parameters (Å, º) top
Cu1—O11.961 (2)C10—C151.405 (9)
Cu1—O31.962 (3)C10—C111.407 (9)
Cu1—O4i1.965 (3)C11—C121.393 (9)
Cu1—O2i1.974 (2)C11—H11A0.93
Cu1—O52.149 (2)C12—C131.395 (10)
Cu1—Cu1i2.6409 (15)C12—H12A0.93
S1—C11.770 (4)C13—C141.395 (8)
S1—C81.784 (4)C13—C161.488 (13)
S2—C101.726 (19)C14—C151.389 (8)
S2—C171.794 (3)C14—H14A0.93
S2—C10'1.796 (15)C15—H15A0.93
O1—C91.245 (4)C16—H16A0.96
O2—C91.253 (4)C16—H16B0.96
O2—Cu1i1.974 (2)C16—H16C0.96
O3—C181.263 (4)C10'—C15'1.369 (8)
O4—C181.250 (4)C10'—C11'1.369 (8)
O4—Cu1i1.965 (3)C11'—C12'1.357 (8)
O5—C191.263 (4)C11'—H11B0.93
C1—C21.374 (5)C12'—C13'1.360 (9)
C1—C61.406 (5)C12'—H12B0.93
C2—C31.358 (5)C13'—C14'1.357 (7)
C2—H20.93C13'—C16'1.523 (12)
C3—C41.399 (6)C14'—C15'1.365 (7)
C3—H30.93C14'—H14B0.93
C4—C51.386 (6)C15'—H15B0.93
C4—C71.509 (6)C16'—H16D0.96
C5—C61.353 (6)C16'—H16E0.96
C5—H50.93C16'—H16F0.96
C6—H60.93C17—C181.504 (5)
C7—H7A0.96C17—H17A0.97
C7—H7B0.96C17—H17B0.97
C7—H7C0.96C19—N11.301 (4)
C8—C91.526 (4)C20—N11.476 (6)
C8—H8A0.97C21—N11.458 (6)
C8—H8B0.97
O1—Cu1—O387.68 (10)C15—C10—C11119.2 (16)
O1—Cu1—O4i90.54 (11)C15—C10—S2113.4 (11)
O3—Cu1—O4i167.97 (9)C11—C10—S2127.4 (10)
O1—Cu1—O2i167.81 (9)C12—C11—C10120.2 (19)
O3—Cu1—O2i90.18 (10)C12—C11—H11A119.9
O4i—Cu1—O2i89.07 (11)C10—C11—H11A119.9
O1—Cu1—O598.89 (9)C11—C12—C13120.8 (18)
O3—Cu1—O599.79 (10)C11—C12—H12A119.6
O4i—Cu1—O592.23 (10)C13—C12—H12A119.6
O2i—Cu1—O593.30 (9)C14—C13—C12118.7 (12)
O1—Cu1—Cu1i86.49 (7)C14—C13—C16122.0 (10)
O3—Cu1—Cu1i86.51 (8)C12—C13—C16119.3 (12)
O4i—Cu1—Cu1i81.51 (8)C15—C14—C13121.6 (8)
O2i—Cu1—Cu1i81.40 (7)C15—C14—H14A119.2
O5—Cu1—Cu1i171.82 (7)C13—C14—H14A119.2
C1—S1—C8102.76 (18)C14—C15—C10119.6 (11)
C10—S2—C17100.1 (4)C14—C15—H15A120.2
C17—S2—C10'105.8 (3)C10—C15—H15A120.2
C9—O1—Cu1120.4 (2)C15'—C10'—C11'117.1 (12)
C9—O2—Cu1i125.5 (2)C15'—C10'—S2120.2 (9)
C18—O3—Cu1120.3 (2)C11'—C10'—S2122.7 (8)
C18—O4—Cu1i126.3 (2)C12'—C11'—C10'119.2 (15)
C19—O5—Cu1115.4 (2)C12'—C11'—H11B120.4
C2—C1—C6117.9 (4)C10'—C11'—H11B120.4
C2—C1—S1125.0 (3)C11'—C12'—C13'125.4 (15)
C6—C1—S1117.1 (3)C11'—C12'—H12B117.3
C3—C2—C1120.7 (3)C13'—C12'—H12B117.3
C3—C2—H2119.6C14'—C13'—C12'113.8 (11)
C1—C2—H2119.6C14'—C13'—C16'124.4 (8)
C2—C3—C4122.2 (4)C12'—C13'—C16'121.8 (10)
C2—C3—H3118.9C13'—C14'—C15'123.2 (7)
C4—C3—H3118.9C13'—C14'—H14B118.4
C5—C4—C3116.4 (4)C15'—C14'—H14B118.4
C5—C4—C7122.7 (4)C14'—C15'—C10'121.1 (9)
C3—C4—C7120.9 (4)C14'—C15'—H15B119.5
C6—C5—C4121.9 (4)C10'—C15'—H15B119.5
C6—C5—H5119.0C13'—C16'—H16D109.5
C4—C5—H5119.0C13'—C16'—H16E109.5
C5—C6—C1120.7 (4)H16D—C16'—H16E109.5
C5—C6—H6119.6C13'—C16'—H16F109.5
C1—C6—H6119.6H16D—C16'—H16F109.5
C4—C7—H7A109.5H16E—C16'—H16F109.5
C4—C7—H7B109.5C18—C17—S2114.9 (2)
H7A—C7—H7B109.5C18—C17—H17A108.5
C4—C7—H7C109.5S2—C17—H17A108.5
H7A—C7—H7C109.5C18—C17—H17B108.5
H7B—C7—H7C109.5S2—C17—H17B108.5
C9—C8—S1117.4 (2)H17A—C17—H17B107.5
C9—C8—H8A107.9O4—C18—O3125.3 (3)
S1—C8—H8A107.9O4—C18—C17117.4 (3)
C9—C8—H8B107.9O3—C18—C17117.3 (3)
S1—C8—H8B107.9O5—C19—N1123.8 (4)
H8A—C8—H8B107.2C19—N1—C21121.7 (4)
O1—C9—O2126.1 (3)C19—N1—C20122.4 (4)
O1—C9—C8119.3 (3)C21—N1—C20115.6 (4)
O2—C9—C8114.6 (3)
O3—Cu1—O1—C986.4 (3)C10'—S2—C10—C1176 (2)
O4i—Cu1—O1—C981.7 (3)C15—C10—C11—C120.5 (12)
O2i—Cu1—O1—C96.3 (7)S2—C10—C11—C12178.9 (10)
O5—Cu1—O1—C9174.1 (3)C10—C11—C12—C130.2 (12)
Cu1i—Cu1—O1—C90.3 (3)C11—C12—C13—C140.1 (17)
O1—Cu1—O3—C1885.9 (2)C11—C12—C13—C16178.4 (9)
O4i—Cu1—O3—C184.2 (6)C12—C13—C14—C150.4 (17)
O2i—Cu1—O3—C1882.1 (2)C16—C13—C14—C15178.1 (10)
O5—Cu1—O3—C18175.5 (2)C13—C14—C15—C100.7 (16)
Cu1i—Cu1—O3—C180.7 (2)C11—C10—C15—C140.8 (15)
O1—Cu1—O5—C19148.0 (3)S2—C10—C15—C14179.4 (8)
O3—Cu1—O5—C19122.8 (3)C10—S2—C10'—C15'122 (3)
O4i—Cu1—O5—C1957.1 (3)C17—S2—C10'—C15'166.6 (8)
O2i—Cu1—O5—C1932.1 (3)C10—S2—C10'—C11'59 (2)
C8—S1—C1—C221.7 (4)C17—S2—C10'—C11'12.3 (11)
C8—S1—C1—C6158.5 (3)C15'—C10'—C11'—C12'3.0 (13)
C6—C1—C2—C32.0 (5)S2—C10'—C11'—C12'178.1 (9)
S1—C1—C2—C3178.2 (3)C10'—C11'—C12'—C13'0.6 (13)
C1—C2—C3—C41.7 (6)C11'—C12'—C13'—C14'1.9 (16)
C2—C3—C4—C50.8 (6)C11'—C12'—C13'—C16'175.8 (9)
C2—C3—C4—C7178.8 (4)C12'—C13'—C14'—C15'2.1 (15)
C3—C4—C5—C63.0 (6)C16'—C13'—C14'—C15'175.6 (10)
C7—C4—C5—C6176.5 (4)C13'—C14'—C15'—C10'0.3 (15)
C4—C5—C6—C12.7 (6)C11'—C10'—C15'—C14'2.8 (15)
C2—C1—C6—C50.1 (6)S2—C10'—C15'—C14'178.2 (7)
S1—C1—C6—C5179.7 (3)C10—S2—C17—C1887.3 (5)
C1—S1—C8—C978.3 (3)C10'—S2—C17—C1871.7 (5)
Cu1—O1—C9—O23.3 (5)Cu1i—O4—C18—O35.3 (5)
Cu1—O1—C9—C8175.4 (2)Cu1i—O4—C18—C17175.3 (2)
Cu1i—O2—C9—O15.5 (5)Cu1—O3—C18—O43.6 (4)
Cu1i—O2—C9—C8173.2 (2)Cu1—O3—C18—C17177.0 (2)
S1—C8—C9—O120.4 (5)S2—C17—C18—O449.0 (4)
S1—C8—C9—O2160.8 (3)S2—C17—C18—O3131.5 (3)
C17—S2—C10—C15142.4 (8)Cu1—O5—C19—N1170.4 (3)
C10'—S2—C10—C15105 (2)O5—C19—N1—C210.5 (7)
C17—S2—C10—C1136.1 (11)O5—C19—N1—C20173.9 (5)
Symmetry code: (i) x+1, y+1, z.
 

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