The dinuclear title compound, [Cd2(C5H10NO2S2)4], is disposed about a centre of inversion and features both bidentate bridging and chelating dithiocarbamate ligands. A three-dimensional network structure arises as a result of substantial hydrogen-bonding interactions.
Supporting information
CCDC reference: 255426
Key indicators
- Single-crystal X-ray study
- T = 223 K
- Mean (C-C) = 0.005 Å
- R factor = 0.041
- wR factor = 0.100
- Data-to-parameter ratio = 25.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cd - S1 .. 6.00 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cd - S4 .. 9.66 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cd - S4_a .. 5.74 su
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Bis[µ-
N,
N-bis(2-hydroxyethyl)dithiocarbamato]-
1:2
κ3S,
S':
S';2:1
κ3S,
S':
S'-bis{[
N,
N-bis(2-
hydroxyethyl)dithiocarbamato-
κ2S,
S']cadmium(II)}
top
Crystal data top
[Cd2(C5H10NO2S2)4] | F(000) = 952 |
Mr = 945.84 | Dx = 1.858 Mg m−3 |
Monoclinic, P21/c | Melting point = 155–156 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71069 Å |
a = 8.1588 (10) Å | Cell parameters from 946 reflections |
b = 8.304 (1) Å | θ = 2.6–29.9° |
c = 25.008 (3) Å | µ = 1.80 mm−1 |
β = 93.956 (2)° | T = 223 K |
V = 1690.3 (4) Å3 | Plate, colourless |
Z = 2 | 0.34 × 0.23 × 0.07 mm |
Data collection top
Bruker AXS SMART CCD diffractometer | 4909 independent reflections |
Radiation source: fine-focus sealed tube | 4665 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω scans | θmax = 30.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −11→10 |
Tmin = 0.630, Tmax = 0.882 | k = −9→11 |
13581 measured reflections | l = −33→34 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.33 | w = 1/[σ2(Fo2) + (0.0385P)2 + 1.1441P] where P = (Fo2 + 2Fc2)/3 |
4909 reflections | (Δ/σ)max < 0.001 |
194 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −1.13 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cd | 0.20786 (3) | 0.05332 (3) | 0.018287 (9) | 0.02444 (8) | |
S1 | 0.49548 (9) | 0.13491 (11) | 0.05704 (3) | 0.02552 (16) | |
S2 | 0.22753 (9) | 0.02723 (10) | 0.12370 (3) | 0.02613 (16) | |
S3 | 0.16315 (9) | 0.23105 (10) | −0.06664 (3) | 0.02558 (16) | |
S4 | −0.08999 (9) | 0.22240 (9) | 0.01379 (3) | 0.02221 (15) | |
O1 | 0.8359 (3) | 0.0293 (3) | 0.20170 (9) | 0.0299 (5) | |
H1 | 0.7846 | −0.0558 | 0.1956 | 0.045* | |
O2 | 0.3093 (3) | 0.2348 (3) | 0.28964 (9) | 0.0311 (5) | |
H2 | 0.2269 | 0.1776 | 0.2925 | 0.047* | |
O3 | 0.0389 (3) | 0.4477 (3) | −0.20992 (10) | 0.0342 (6) | |
H3 | −0.0137 | 0.4614 | −0.2392 | 0.051* | |
O4 | −0.4345 (3) | 0.4186 (4) | −0.13749 (11) | 0.0393 (6) | |
H4 | −0.5059 | 0.3597 | −0.1525 | 0.059* | |
N1 | 0.5101 (3) | 0.1538 (3) | 0.16342 (10) | 0.0216 (5) | |
N2 | −0.1088 (3) | 0.4077 (3) | −0.07434 (10) | 0.0212 (5) | |
C1 | 0.4196 (3) | 0.1095 (3) | 0.11942 (11) | 0.0189 (5) | |
C2 | 0.6653 (4) | 0.2434 (4) | 0.16103 (12) | 0.0238 (6) | |
H2A | 0.6829 | 0.3094 | 0.1934 | 0.029* | |
H2B | 0.6565 | 0.3160 | 0.1301 | 0.029* | |
C3 | 0.8125 (4) | 0.1334 (4) | 0.15649 (13) | 0.0254 (6) | |
H3A | 0.7961 | 0.0685 | 0.1238 | 0.031* | |
H3B | 0.9113 | 0.1990 | 0.1535 | 0.031* | |
C4 | 0.4536 (4) | 0.1242 (4) | 0.21711 (11) | 0.0233 (6) | |
H4A | 0.5491 | 0.1189 | 0.2431 | 0.028* | |
H4B | 0.3976 | 0.0198 | 0.2173 | 0.028* | |
C5 | 0.3377 (4) | 0.2543 (4) | 0.23415 (12) | 0.0265 (6) | |
H5A | 0.3856 | 0.3606 | 0.2284 | 0.032* | |
H5B | 0.2332 | 0.2473 | 0.2124 | 0.032* | |
C6 | −0.0213 (3) | 0.2975 (3) | −0.04635 (11) | 0.0178 (5) | |
C7 | −0.0426 (4) | 0.4817 (4) | −0.12164 (12) | 0.0247 (6) | |
H7A | 0.0752 | 0.5007 | −0.1140 | 0.030* | |
H7B | −0.0954 | 0.5866 | −0.1280 | 0.030* | |
C8 | −0.0671 (4) | 0.3813 (4) | −0.17219 (12) | 0.0282 (6) | |
H8A | −0.0386 | 0.2686 | −0.1646 | 0.034* | |
H8B | −0.1819 | 0.3864 | −0.1865 | 0.034* | |
C9 | −0.2673 (4) | 0.4697 (4) | −0.05719 (14) | 0.0271 (6) | |
H9A | −0.2767 | 0.5840 | −0.0667 | 0.032* | |
H9B | −0.2668 | 0.4616 | −0.0181 | 0.032* | |
C10 | −0.4170 (4) | 0.3815 (5) | −0.08195 (15) | 0.0323 (7) | |
H10A | −0.4032 | 0.2651 | −0.0769 | 0.039* | |
H10B | −0.5154 | 0.4152 | −0.0646 | 0.039* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd | 0.02407 (12) | 0.02433 (12) | 0.02371 (12) | −0.00197 (8) | −0.00717 (8) | 0.00169 (8) |
S1 | 0.0187 (3) | 0.0397 (4) | 0.0184 (3) | −0.0002 (3) | 0.0028 (3) | −0.0002 (3) |
S2 | 0.0193 (3) | 0.0349 (4) | 0.0242 (4) | −0.0074 (3) | 0.0015 (3) | −0.0029 (3) |
S3 | 0.0189 (3) | 0.0333 (4) | 0.0249 (3) | 0.0046 (3) | 0.0041 (3) | 0.0064 (3) |
S4 | 0.0267 (3) | 0.0233 (3) | 0.0168 (3) | −0.0038 (3) | 0.0029 (3) | −0.0014 (3) |
O1 | 0.0281 (12) | 0.0337 (13) | 0.0268 (11) | −0.0025 (9) | −0.0056 (9) | 0.0050 (9) |
O2 | 0.0285 (11) | 0.0459 (15) | 0.0192 (10) | 0.0024 (10) | 0.0040 (9) | −0.0064 (10) |
O3 | 0.0272 (12) | 0.0539 (16) | 0.0217 (11) | −0.0011 (11) | 0.0018 (9) | 0.0066 (11) |
O4 | 0.0283 (13) | 0.0487 (16) | 0.0394 (14) | −0.0051 (11) | −0.0076 (11) | 0.0002 (12) |
N1 | 0.0166 (11) | 0.0275 (12) | 0.0206 (11) | −0.0005 (9) | 0.0010 (9) | −0.0039 (10) |
N2 | 0.0206 (11) | 0.0206 (11) | 0.0224 (12) | 0.0004 (9) | 0.0003 (9) | 0.0006 (9) |
C1 | 0.0172 (12) | 0.0204 (13) | 0.0192 (12) | 0.0032 (10) | 0.0019 (10) | −0.0037 (10) |
C2 | 0.0200 (13) | 0.0248 (14) | 0.0264 (14) | −0.0042 (11) | 0.0000 (11) | −0.0024 (11) |
C3 | 0.0193 (13) | 0.0309 (16) | 0.0265 (14) | 0.0001 (11) | 0.0042 (11) | 0.0038 (12) |
C4 | 0.0216 (13) | 0.0299 (15) | 0.0179 (12) | 0.0028 (11) | −0.0013 (10) | −0.0016 (11) |
C5 | 0.0289 (15) | 0.0302 (16) | 0.0205 (14) | 0.0031 (12) | 0.0030 (11) | −0.0035 (12) |
C6 | 0.0188 (12) | 0.0191 (12) | 0.0154 (11) | −0.0015 (10) | 0.0010 (9) | −0.0006 (9) |
C7 | 0.0292 (15) | 0.0218 (14) | 0.0230 (14) | 0.0004 (11) | 0.0015 (11) | 0.0053 (11) |
C8 | 0.0264 (15) | 0.0370 (18) | 0.0212 (14) | −0.0052 (13) | 0.0007 (11) | 0.0000 (12) |
C9 | 0.0241 (14) | 0.0262 (15) | 0.0311 (16) | 0.0077 (12) | 0.0040 (12) | −0.0039 (12) |
C10 | 0.0215 (14) | 0.0350 (18) | 0.0405 (19) | 0.0035 (13) | 0.0023 (13) | 0.0015 (14) |
Geometric parameters (Å, º) top
Cd—S1 | 2.5673 (8) | N2—C7 | 1.468 (4) |
Cd—S2 | 2.6389 (9) | N2—C9 | 1.483 (4) |
Cd—S3 | 2.5915 (8) | C2—C3 | 1.519 (4) |
Cd—S4 | 2.8021 (9) | C2—H2A | 0.9800 |
Cd—S4i | 2.5892 (8) | C2—H2B | 0.9800 |
S1—C1 | 1.730 (3) | C3—H3A | 0.9800 |
S2—C1 | 1.720 (3) | C3—H3B | 0.9800 |
S3—C6 | 1.712 (3) | C4—C5 | 1.517 (4) |
S4—C6 | 1.756 (3) | C4—H4A | 0.9800 |
S4—Cdi | 2.5892 (8) | C4—H4B | 0.9800 |
O1—C3 | 1.426 (4) | C5—H5A | 0.9800 |
O1—H1 | 0.8300 | C5—H5B | 0.9800 |
O2—C5 | 1.432 (4) | C7—C8 | 1.516 (4) |
O2—H2 | 0.8300 | C7—H7A | 0.9800 |
O3—C8 | 1.434 (4) | C7—H7B | 0.9800 |
O3—H3 | 0.8300 | C8—H8A | 0.9800 |
O4—C10 | 1.420 (4) | C8—H8B | 0.9800 |
O4—H4 | 0.8300 | C9—C10 | 1.519 (5) |
N1—C1 | 1.334 (4) | C9—H9A | 0.9800 |
N1—C4 | 1.470 (4) | C9—H9B | 0.9800 |
N1—C2 | 1.474 (4) | C10—H10A | 0.9800 |
N2—C6 | 1.330 (4) | C10—H10B | 0.9800 |
| | | |
S1—Cd—S2 | 69.73 (2) | H3A—C3—H3B | 108.0 |
S1—Cd—S3 | 103.44 (3) | N1—C4—C5 | 112.2 (3) |
S1—Cd—S4 | 130.58 (3) | N1—C4—H4A | 109.2 |
S1—Cd—S4i | 131.35 (3) | C5—C4—H4A | 109.2 |
S2—Cd—S3 | 149.42 (3) | N1—C4—H4B | 109.2 |
S2—Cd—S4 | 94.24 (2) | C5—C4—H4B | 109.2 |
S2—Cd—S4i | 103.45 (2) | H4A—C4—H4B | 107.9 |
S3—Cd—S4 | 66.99 (2) | O2—C5—C4 | 109.7 (3) |
S3—Cd—S4i | 102.79 (3) | O2—C5—H5A | 109.7 |
S4—Cd—S4i | 97.36 (2) | C4—C5—H5A | 109.7 |
Cd—S1—C1 | 86.20 (10) | O2—C5—H5B | 109.7 |
Cd—S2—C1 | 84.15 (10) | C4—C5—H5B | 109.7 |
Cd—S3—C6 | 91.01 (10) | H5A—C5—H5B | 108.2 |
Cd—S4—C6 | 83.40 (10) | S3—C6—S4 | 118.58 (16) |
Cdi—S4—C6 | 100.52 (9) | S3—C6—N2 | 121.1 (2) |
Cd—S4—Cdi | 82.64 (2) | S4—C6—N2 | 120.3 (2) |
C3—O1—H1 | 109.5 | N2—C7—C8 | 114.1 (3) |
C5—O2—H2 | 109.5 | N2—C7—H7A | 108.7 |
C8—O3—H3 | 109.5 | C8—C7—H7A | 108.7 |
C10—O4—H4 | 109.5 | N2—C7—H7B | 108.7 |
C1—N1—C2 | 122.3 (2) | C8—C7—H7B | 108.7 |
C1—N1—C4 | 121.1 (2) | H7A—C7—H7B | 107.6 |
C4—N1—C2 | 116.5 (2) | O3—C8—C7 | 106.7 (3) |
C6—N2—C7 | 119.9 (2) | O3—C8—H8A | 110.4 |
C6—N2—C9 | 122.3 (3) | C7—C8—H8A | 110.4 |
C7—N2—C9 | 117.7 (2) | O3—C8—H8B | 110.4 |
S1—C1—S2 | 119.25 (16) | C7—C8—H8B | 110.4 |
S1—C1—N1 | 119.9 (2) | H8A—C8—H8B | 108.6 |
S2—C1—N1 | 120.9 (2) | N2—C9—C10 | 114.0 (3) |
N1—C2—C3 | 112.7 (3) | N2—C9—H9A | 108.7 |
N1—C2—H2A | 109.1 | C10—C9—H9A | 108.7 |
C3—C2—H2A | 109.1 | N2—C9—H9B | 108.7 |
N1—C2—H2B | 109.1 | C10—C9—H9B | 108.7 |
C3—C2—H2B | 109.1 | H9A—C9—H9B | 107.6 |
H2A—C2—H2B | 107.8 | O4—C10—C9 | 108.5 (3) |
O1—C3—C2 | 111.7 (2) | O4—C10—H10A | 110.0 |
O1—C3—H3A | 109.3 | C9—C10—H10A | 110.0 |
C2—C3—H3A | 109.3 | O4—C10—H10B | 110.0 |
O1—C3—H3B | 109.3 | C9—C10—H10B | 110.0 |
C2—C3—H3B | 109.3 | H10A—C10—H10B | 108.4 |
Symmetry code: (i) −x, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2ii | 0.83 | 1.95 | 2.732 (4) | 158 |
O2—H2···O3iii | 0.83 | 1.85 | 2.677 (4) | 173 |
O3—H3···O1iv | 0.83 | 1.86 | 2.676 (3) | 169 |
O4—H4···O2iv | 0.83 | 2.16 | 2.964 (4) | 162 |
Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z+1/2; (iv) x−1, −y+1/2, z−1/2. |