Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806055346/xu2187sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806055346/xu2187Isup2.hkl |
CCDC reference: 636841
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.010 Å
- R factor = 0.035
- wR factor = 0.088
- Data-to-parameter ratio = 21.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT231_ALERT_4_C Hirshfeld Test (Solvent) C16 - C17 .. 5.30 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cd1 - S4 .. 6.12 su PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C16 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N2 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.40 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.29 PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C6 H8 N PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 C6 H8 N
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 2 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
(C6H8N)2[Cd(C3S5)2] | F(000) = 1384 |
Mr = 693.33 | Dx = 1.750 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4431 reflections |
a = 14.4624 (12) Å | θ = 3.3–26.9° |
b = 13.5970 (11) Å | µ = 1.64 mm−1 |
c = 14.1880 (11) Å | T = 293 K |
β = 109.369 (1)° | Plate, purple–red |
V = 2632.1 (4) Å3 | 0.24 × 0.23 × 0.05 mm |
Z = 4 |
Bruker APEX2 CCD area-detector diffractometer | 6032 independent reflections |
Radiation source: fine-focus sealed tube | 4441 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: multi-scan (APEX2; Bruker, 2005) | h = −17→18 |
Tmin = 0.694, Tmax = 0.917 | k = −9→17 |
13401 measured reflections | l = −18→7 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0389P)2 + 1.0462P] where P = (Fo2 + 2Fc2)/3 |
6032 reflections | (Δ/σ)max = 0.001 |
282 parameters | Δρmax = 0.53 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
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 | ||
N1 | −0.1291 (4) | 0.3127 (3) | 0.1262 (2) | 0.0864 (11) | |
N2 | 1.4267 (3) | 0.1587 (2) | 0.3013 (2) | 0.0785 (10) | |
C1 | 0.2814 (2) | 0.4280 (2) | 0.2073 (3) | 0.0618 (9) | |
C2 | 0.4673 (2) | 0.4145 (2) | 0.2215 (2) | 0.0475 (7) | |
C3 | 0.4680 (2) | 0.4137 (2) | 0.3174 (2) | 0.0474 (7) | |
C4 | 0.9196 (2) | 0.3394 (2) | 0.3854 (2) | 0.0474 (7) | |
C5 | 0.8867 (2) | 0.2458 (2) | 0.3826 (2) | 0.0451 (7) | |
C6 | 1.0733 (2) | 0.2281 (3) | 0.4019 (2) | 0.0559 (8) | |
C7 | −0.1278 (6) | 0.4180 (5) | 0.1175 (4) | 0.167 (3) | |
H7A | −0.1923 | 0.4435 | 0.1072 | 0.250* | |
H7B | −0.1075 | 0.4354 | 0.0618 | 0.250* | |
H7C | −0.0828 | 0.4453 | 0.1776 | 0.250* | |
C8 | −0.2107 (4) | 0.2670 (5) | 0.1253 (3) | 0.0974 (15) | |
H8 | −0.2665 | 0.3032 | 0.1212 | 0.117* | |
C9 | −0.2123 (5) | 0.1700 (7) | 0.1301 (4) | 0.117 (2) | |
H9 | −0.2691 | 0.1388 | 0.1316 | 0.141* | |
C10 | −0.1363 (7) | 0.1168 (5) | 0.1329 (4) | 0.122 (2) | |
H10 | −0.1411 | 0.0486 | 0.1334 | 0.146* | |
C11 | −0.0536 (5) | 0.1570 (6) | 0.1350 (4) | 0.1070 (17) | |
H11 | 0.0002 | 0.1180 | 0.1381 | 0.128* | |
C12 | −0.0473 (4) | 0.2588 (5) | 0.1326 (3) | 0.0977 (16) | |
H12 | 0.0110 | 0.2896 | 0.1352 | 0.117* | |
C13 | 1.4585 (6) | 0.1552 (4) | 0.4089 (4) | 0.156 (3) | |
H13A | 1.5260 | 0.1746 | 0.4355 | 0.234* | |
H13B | 1.4514 | 0.0895 | 0.4302 | 0.234* | |
H13C | 1.4192 | 0.1993 | 0.4327 | 0.234* | |
C14 | 1.3304 (4) | 0.1654 (3) | 0.2461 (4) | 0.0867 (13) | |
H14 | 1.2836 | 0.1699 | 0.2778 | 0.104* | |
C15 | 1.3026 (4) | 0.1657 (4) | 0.1476 (5) | 0.1018 (16) | |
H15 | 1.2364 | 0.1712 | 0.1107 | 0.122* | |
C16 | 1.3665 (7) | 0.1584 (4) | 0.1013 (4) | 0.122 (2) | |
H16 | 1.3454 | 0.1575 | 0.0318 | 0.146* | |
C17 | 1.4615 (6) | 0.1522 (4) | 0.1526 (6) | 0.107 (2) | |
H17 | 1.5066 | 0.1476 | 0.1188 | 0.129* | |
C18 | 1.4933 (4) | 0.1524 (3) | 0.2536 (5) | 0.0932 (15) | |
H18 | 1.5598 | 0.1482 | 0.2897 | 0.112* | |
Cd1 | 0.692162 (16) | 0.371879 (19) | 0.344166 (18) | 0.05574 (9) | |
S1 | 0.16088 (7) | 0.43368 (9) | 0.16789 (11) | 0.0923 (4) | |
S2 | 0.35143 (6) | 0.42627 (7) | 0.13049 (7) | 0.0619 (2) | |
S3 | 0.35278 (6) | 0.42363 (7) | 0.33143 (7) | 0.0642 (2) | |
S4 | 0.56473 (6) | 0.40392 (7) | 0.17572 (6) | 0.0569 (2) | |
S5 | 0.56732 (6) | 0.40260 (8) | 0.42737 (6) | 0.0611 (2) | |
S6 | 0.85600 (6) | 0.44964 (7) | 0.37631 (8) | 0.0647 (2) | |
S7 | 0.76922 (6) | 0.20357 (6) | 0.36866 (7) | 0.0552 (2) | |
S8 | 1.04368 (6) | 0.35074 (7) | 0.39865 (7) | 0.0628 (2) | |
S9 | 0.97581 (5) | 0.15422 (6) | 0.39551 (6) | 0.0534 (2) | |
S10 | 1.18316 (7) | 0.18619 (9) | 0.41022 (9) | 0.0834 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.133 (4) | 0.075 (3) | 0.0525 (19) | −0.010 (2) | 0.033 (2) | −0.0091 (17) |
N2 | 0.120 (3) | 0.0491 (19) | 0.065 (2) | −0.0102 (19) | 0.029 (2) | −0.0036 (15) |
C1 | 0.0463 (17) | 0.0415 (19) | 0.092 (3) | 0.0025 (14) | 0.0157 (17) | −0.0034 (17) |
C2 | 0.0428 (15) | 0.0393 (17) | 0.0575 (18) | 0.0021 (13) | 0.0129 (13) | −0.0001 (14) |
C3 | 0.0403 (15) | 0.0437 (17) | 0.0573 (18) | 0.0036 (13) | 0.0152 (13) | 0.0020 (14) |
C4 | 0.0409 (15) | 0.0554 (19) | 0.0439 (16) | −0.0020 (14) | 0.0112 (12) | −0.0015 (14) |
C5 | 0.0384 (14) | 0.0535 (19) | 0.0413 (15) | −0.0006 (13) | 0.0104 (12) | −0.0027 (13) |
C6 | 0.0427 (16) | 0.075 (2) | 0.0477 (17) | 0.0003 (15) | 0.0119 (13) | −0.0050 (16) |
C7 | 0.313 (11) | 0.083 (4) | 0.103 (4) | 0.002 (5) | 0.068 (6) | −0.011 (3) |
C8 | 0.085 (3) | 0.142 (5) | 0.064 (3) | −0.008 (3) | 0.022 (2) | −0.002 (3) |
C9 | 0.130 (5) | 0.148 (6) | 0.066 (3) | −0.053 (5) | 0.022 (3) | −0.015 (4) |
C10 | 0.194 (8) | 0.101 (5) | 0.071 (3) | −0.012 (5) | 0.045 (5) | 0.002 (3) |
C11 | 0.124 (5) | 0.132 (6) | 0.066 (3) | 0.019 (4) | 0.033 (3) | 0.008 (3) |
C12 | 0.094 (3) | 0.144 (5) | 0.059 (3) | −0.023 (3) | 0.030 (2) | 0.000 (3) |
C13 | 0.272 (9) | 0.092 (4) | 0.073 (3) | −0.026 (5) | 0.016 (4) | −0.010 (3) |
C14 | 0.092 (3) | 0.074 (3) | 0.112 (4) | 0.001 (2) | 0.057 (3) | 0.002 (3) |
C15 | 0.117 (4) | 0.072 (3) | 0.103 (4) | 0.008 (3) | 0.019 (3) | 0.006 (3) |
C16 | 0.221 (8) | 0.070 (3) | 0.086 (4) | 0.023 (4) | 0.068 (5) | 0.003 (3) |
C17 | 0.154 (5) | 0.060 (3) | 0.151 (6) | 0.022 (3) | 0.109 (5) | 0.021 (3) |
C18 | 0.080 (3) | 0.047 (2) | 0.154 (5) | 0.000 (2) | 0.041 (3) | 0.010 (3) |
Cd1 | 0.04440 (13) | 0.06217 (18) | 0.05960 (16) | 0.00753 (11) | 0.01586 (10) | 0.00337 (12) |
S1 | 0.0423 (5) | 0.0857 (8) | 0.1394 (10) | 0.0015 (5) | 0.0173 (6) | −0.0053 (7) |
S2 | 0.0463 (4) | 0.0627 (6) | 0.0658 (5) | 0.0030 (4) | 0.0040 (4) | −0.0022 (4) |
S3 | 0.0505 (4) | 0.0670 (6) | 0.0805 (6) | 0.0077 (4) | 0.0290 (4) | 0.0028 (5) |
S4 | 0.0509 (4) | 0.0695 (6) | 0.0501 (4) | 0.0068 (4) | 0.0163 (4) | 0.0020 (4) |
S5 | 0.0527 (5) | 0.0818 (6) | 0.0500 (4) | 0.0108 (4) | 0.0184 (4) | 0.0058 (4) |
S6 | 0.0553 (5) | 0.0511 (5) | 0.0871 (6) | −0.0009 (4) | 0.0228 (4) | 0.0015 (5) |
S7 | 0.0412 (4) | 0.0536 (5) | 0.0704 (5) | −0.0006 (3) | 0.0181 (4) | 0.0013 (4) |
S8 | 0.0441 (4) | 0.0668 (6) | 0.0755 (6) | −0.0082 (4) | 0.0172 (4) | −0.0029 (5) |
S9 | 0.0431 (4) | 0.0573 (5) | 0.0571 (5) | 0.0041 (3) | 0.0131 (3) | −0.0045 (4) |
S10 | 0.0448 (5) | 0.1068 (9) | 0.1002 (8) | 0.0087 (5) | 0.0261 (5) | −0.0069 (7) |
N1—C8 | 1.330 (6) | C8—C9 | 1.322 (8) |
N1—C12 | 1.370 (6) | C8—H8 | 0.9300 |
N1—C7 | 1.437 (7) | C9—C10 | 1.306 (9) |
N2—C18 | 1.351 (6) | C9—H9 | 0.9300 |
N2—C14 | 1.356 (6) | C10—C11 | 1.306 (9) |
N2—C13 | 1.442 (6) | C10—H10 | 0.9300 |
C1—S1 | 1.647 (3) | C11—C12 | 1.389 (8) |
C1—S2 | 1.716 (4) | C11—H11 | 0.9300 |
C1—S3 | 1.722 (4) | C12—H12 | 0.9300 |
C2—C3 | 1.358 (4) | C13—H13A | 0.9600 |
C2—S4 | 1.742 (3) | C13—H13B | 0.9600 |
C2—S2 | 1.751 (3) | C13—H13C | 0.9600 |
C3—S5 | 1.742 (3) | C14—C15 | 1.319 (7) |
C3—S3 | 1.748 (3) | C14—H14 | 0.9300 |
C4—C5 | 1.355 (4) | C15—C16 | 1.304 (8) |
C4—S6 | 1.741 (3) | C15—H15 | 0.9300 |
C4—S8 | 1.747 (3) | C16—C17 | 1.327 (9) |
C5—S7 | 1.742 (3) | C16—H16 | 0.9300 |
C5—S9 | 1.757 (3) | C17—C18 | 1.353 (8) |
C6—S10 | 1.655 (3) | C17—H17 | 0.9300 |
C6—S9 | 1.709 (3) | C18—H18 | 0.9300 |
C6—S8 | 1.718 (4) | Cd1—S6 | 2.4947 (9) |
C7—H7A | 0.9600 | Cd1—S5 | 2.4983 (9) |
C7—H7B | 0.9600 | Cd1—S7 | 2.5185 (9) |
C7—H7C | 0.9600 | Cd1—S4 | 2.5252 (9) |
C8—N1—C12 | 119.7 (5) | C10—C11—H11 | 120.5 |
C8—N1—C7 | 120.1 (6) | C12—C11—H11 | 120.5 |
C12—N1—C7 | 120.2 (6) | N1—C12—C11 | 118.2 (5) |
C18—N2—C14 | 118.7 (4) | N1—C12—H12 | 120.9 |
C18—N2—C13 | 119.9 (6) | C11—C12—H12 | 120.9 |
C14—N2—C13 | 121.4 (5) | N2—C13—H13A | 109.5 |
S1—C1—S2 | 124.5 (2) | N2—C13—H13B | 109.5 |
S1—C1—S3 | 123.8 (2) | H13A—C13—H13B | 109.5 |
S2—C1—S3 | 111.67 (18) | N2—C13—H13C | 109.5 |
C3—C2—S4 | 129.4 (2) | H13A—C13—H13C | 109.5 |
C3—C2—S2 | 115.3 (2) | H13B—C13—H13C | 109.5 |
S4—C2—S2 | 115.32 (18) | C15—C14—N2 | 120.4 (4) |
C2—C3—S5 | 128.9 (2) | C15—C14—H14 | 119.8 |
C2—C3—S3 | 115.1 (2) | N2—C14—H14 | 119.8 |
S5—C3—S3 | 116.02 (18) | C16—C15—C14 | 121.1 (6) |
C5—C4—S6 | 129.4 (2) | C16—C15—H15 | 119.5 |
C5—C4—S8 | 115.1 (2) | C14—C15—H15 | 119.5 |
S6—C4—S8 | 115.51 (18) | C15—C16—C17 | 120.5 (6) |
C4—C5—S7 | 129.2 (2) | C15—C16—H16 | 119.8 |
C4—C5—S9 | 115.1 (2) | C17—C16—H16 | 119.8 |
S7—C5—S9 | 115.64 (18) | C16—C17—C18 | 120.4 (5) |
S10—C6—S9 | 123.8 (2) | C16—C17—H17 | 119.8 |
S10—C6—S8 | 124.1 (2) | C18—C17—H17 | 119.8 |
S9—C6—S8 | 112.03 (17) | N2—C18—C17 | 118.9 (5) |
N1—C7—H7A | 109.5 | N2—C18—H18 | 120.6 |
N1—C7—H7B | 109.5 | C17—C18—H18 | 120.6 |
H7A—C7—H7B | 109.5 | S6—Cd1—S5 | 129.36 (3) |
N1—C7—H7C | 109.5 | S6—Cd1—S7 | 90.57 (3) |
H7A—C7—H7C | 109.5 | S5—Cd1—S7 | 116.28 (3) |
H7B—C7—H7C | 109.5 | S6—Cd1—S4 | 116.79 (3) |
C9—C8—N1 | 119.8 (6) | S5—Cd1—S4 | 90.19 (3) |
C9—C8—H8 | 120.1 | S7—Cd1—S4 | 115.98 (3) |
N1—C8—H8 | 120.1 | C1—S2—C2 | 98.93 (16) |
C10—C9—C8 | 121.6 (7) | C1—S3—C3 | 99.01 (16) |
C10—C9—H9 | 119.2 | C2—S4—Cd1 | 95.06 (11) |
C8—C9—H9 | 119.2 | C3—S5—Cd1 | 95.84 (10) |
C11—C10—C9 | 121.7 (7) | C4—S6—Cd1 | 95.47 (10) |
C11—C10—H10 | 119.2 | C5—S7—Cd1 | 94.98 (11) |
C9—C10—H10 | 119.2 | C6—S8—C4 | 98.94 (15) |
C10—C11—C12 | 118.9 (6) | C6—S9—C5 | 98.76 (16) |
S4—C2—C3—S5 | 0.5 (5) | C2—C3—S3—C1 | 1.3 (3) |
S2—C2—C3—S5 | 179.59 (19) | S5—C3—S3—C1 | −177.93 (19) |
S4—C2—C3—S3 | −178.64 (19) | C3—C2—S4—Cd1 | 5.1 (3) |
S2—C2—C3—S3 | 0.5 (3) | S2—C2—S4—Cd1 | −174.02 (15) |
S6—C4—C5—S7 | 0.1 (5) | S6—Cd1—S4—C2 | −141.30 (11) |
S8—C4—C5—S7 | −179.08 (17) | S5—Cd1—S4—C2 | −5.89 (11) |
S6—C4—C5—S9 | −179.51 (18) | S7—Cd1—S4—C2 | 113.72 (11) |
S8—C4—C5—S9 | 1.4 (3) | C2—C3—S5—Cd1 | −5.8 (3) |
C12—N1—C8—C9 | −0.2 (6) | S3—C3—S5—Cd1 | 173.33 (16) |
C7—N1—C8—C9 | 177.9 (5) | S6—Cd1—S5—C3 | 131.90 (11) |
N1—C8—C9—C10 | −2.1 (8) | S7—Cd1—S5—C3 | −113.30 (11) |
C8—C9—C10—C11 | 2.8 (9) | S4—Cd1—S5—C3 | 6.05 (11) |
C9—C10—C11—C12 | −1.1 (9) | C5—C4—S6—Cd1 | −4.2 (3) |
C8—N1—C12—C11 | 1.8 (6) | S8—C4—S6—Cd1 | 174.93 (15) |
C7—N1—C12—C11 | −176.3 (4) | S5—Cd1—S6—C4 | 130.07 (10) |
C10—C11—C12—N1 | −1.1 (7) | S7—Cd1—S6—C4 | 4.57 (10) |
C18—N2—C14—C15 | 0.1 (7) | S4—Cd1—S6—C4 | −115.15 (10) |
C13—N2—C14—C15 | −178.1 (5) | C4—C5—S7—Cd1 | 4.1 (3) |
N2—C14—C15—C16 | 0.8 (8) | S9—C5—S7—Cd1 | −176.35 (14) |
C14—C15—C16—C17 | −1.1 (9) | S6—Cd1—S7—C5 | −4.55 (10) |
C15—C16—C17—C18 | 0.6 (9) | S5—Cd1—S7—C5 | −139.96 (10) |
C14—N2—C18—C17 | −0.6 (6) | S4—Cd1—S7—C5 | 115.87 (10) |
C13—N2—C18—C17 | 177.6 (4) | S10—C6—S8—C4 | 178.0 (2) |
C16—C17—C18—N2 | 0.2 (8) | S9—C6—S8—C4 | −2.0 (2) |
S1—C1—S2—C2 | −177.5 (2) | C5—C4—S8—C6 | 0.4 (3) |
S3—C1—S2—C2 | 2.8 (2) | S6—C4—S8—C6 | −178.87 (17) |
C3—C2—S2—C1 | −2.0 (3) | S10—C6—S9—C5 | −177.4 (2) |
S4—C2—S2—C1 | 177.22 (18) | S8—C6—S9—C5 | 2.6 (2) |
S1—C1—S3—C3 | 177.7 (2) | C4—C5—S9—C6 | −2.4 (3) |
S2—C1—S3—C3 | −2.6 (2) | S7—C5—S9—C6 | 177.94 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···S1 | 0.93 | 2.84 | 3.737 (6) | 161 |
C14—H14···S10 | 0.93 | 2.74 | 3.650 (5) | 167 |