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The title compound, (C7H10N)[Sb(C6H5)2(C3OS4)2], is a further example of a salt containing SbV of the form [Q][R2Sb(dmio)2], with Q an onium counter-cation and R = aryl. It is compared, particularly in terms of the packing of the ions in the unit cell, with other members of the series.
Supporting information
CCDC reference: 226651
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.005 Å
- R factor = 0.038
- wR factor = 0.072
- Data-to-parameter ratio = 31.2
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.96
| Author Response: ... Data is better than 99% complete for theta(max) = 27.5 deg.
|
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
Tmin and Tmax reported: 0.845 0.928
Tmin and Tmax expected: 0.692 0.942
RR = 1.240
Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.24
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.01
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.16
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... S6
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... N1
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C21
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
1,4-Dimethylpyridinium
bis(2-oxo-1,3-dithiole-4,5-dithiolato)diphenylantimonate(1-)
top
Crystal data top
(C7H10N)[Sb(C6H5)2(C3OS4)2] | Z = 2 |
Mr = 744.65 | F(000) = 744 |
Triclinic, P1 | Dx = 1.646 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.7513 (5) Å | Cell parameters from 4647 reflections |
b = 12.0130 (6) Å | θ = 2.2–30.8° |
c = 13.5273 (6) Å | µ = 1.50 mm−1 |
α = 94.063 (1)° | T = 291 K |
β = 112.126 (1)° | Plate, dark_red |
γ = 108.137 (1)° | 0.39 × 0.21 × 0.04 mm |
V = 1502.53 (12) Å3 | |
Data collection top
Bruker SMART 1000 CCD area-detector diffractometer | 10417 independent reflections |
Radiation source: fine-focus sealed tube | 6570 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 32.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −10→16 |
Tmin = 0.845, Tmax = 0.928 | k = −18→17 |
15605 measured reflections | l = −20→20 |
Refinement top
Refinement on F2 | Primary atom site location: heavy-atom method |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 0.88 | w = 1/[σ2(Fo2) + (0.0267P)2] where P = (Fo2 + 2Fc2)/3 |
10417 reflections | (Δ/σ)max = 0.001 |
334 parameters | Δρmax = 0.69 e Å−3 |
0 restraints | Δρmin = −0.32 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. Least-squares planes (x,y,z in crystal coordinates) and
deviations from them (* indicates atom used to define plane) - 6.7223 (0.0023) x + 3.0493 (0.0035) y + 12.5421 (0.0015)
z = 6.3576 (0.0023) * 0.0412 (0.0008) S1 * 0.0176 (0.0008) S2 * -0.0585
(0.0020) C1 * -0.0545 (0.0019) C2 * 0.0145 (0.0008) S3 * 0.0396 (0.0007) S4
0.0542 (0.0032) C3 0.0923 (0.0028) O1 1.5944 (0.0009) Sb1 Rms deviation of fitted atoms = 0.0412 - 2.4850 (0.0033) x + 11.6653 (0.0010) y + 1.4211 (0.0044)
z = 6.8350 (0.0027) Angle to previous plane (with approximate e.s.d.) = 67.67 (0.03) * 0.0342
(0.0008) S5 * 0.0277 (0.0008) S6 * -0.0585 (0.0020) C4 * -0.0607 (0.0021) C5 *
0.0244 (0.0008) S7 * 0.0329 (0.0008) S8 0.0454 (0.0035) C6 0.0335 (0.0032) O2
1.6447 (0.0010) Sb1 Rms deviation of fitted atoms = 0.0423 Distance SS
3.6013 (0.0013) S1 - S1_$5 Angle ANG 177.93 (0.03) O1 - Sb1 - O2 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Sb1 | 0.421630 (17) | 0.733698 (14) | 0.681622 (13) | 0.03959 (5) | |
S1 | 0.45887 (7) | 0.86198 (7) | 0.54656 (6) | 0.05796 (19) | |
S2 | 0.24662 (7) | 0.57986 (6) | 0.49951 (5) | 0.05231 (16) | |
C1 | 0.2770 (3) | 0.8025 (2) | 0.4556 (2) | 0.0476 (6) | |
C2 | 0.1896 (3) | 0.6869 (2) | 0.43718 (19) | 0.0448 (6) | |
S3 | 0.19484 (8) | 0.89987 (7) | 0.39370 (7) | 0.0672 (2) | |
S4 | 0.00604 (7) | 0.65030 (6) | 0.35519 (6) | 0.05879 (18) | |
C3 | 0.0174 (3) | 0.7930 (3) | 0.3278 (2) | 0.0607 (7) | |
O1 | −0.0849 (2) | 0.8162 (2) | 0.2703 (2) | 0.0872 (7) | |
S5 | 0.39255 (7) | 0.57547 (6) | 0.79636 (5) | 0.05075 (16) | |
S6 | 0.59876 (8) | 0.63498 (8) | 0.66380 (5) | 0.05920 (19) | |
C4 | 0.5764 (3) | 0.5996 (2) | 0.8544 (2) | 0.0454 (6) | |
C5 | 0.6611 (3) | 0.6242 (2) | 0.7994 (2) | 0.0476 (6) | |
S7 | 0.66348 (8) | 0.60820 (8) | 0.99454 (6) | 0.0646 (2) | |
S8 | 0.84595 (8) | 0.66227 (8) | 0.87580 (6) | 0.0639 (2) | |
C6 | 0.8405 (3) | 0.6467 (3) | 1.0031 (2) | 0.0686 (8) | |
O2 | 0.9450 (2) | 0.6579 (3) | 1.08531 (18) | 0.0983 (8) | |
C7 | 0.5954 (3) | 0.8689 (2) | 0.8200 (2) | 0.0489 (6) | |
C8 | 0.5750 (3) | 0.8930 (3) | 0.9124 (3) | 0.0717 (9) | |
H8 | 0.4867 | 0.8535 | 0.9141 | 0.086* | |
C9 | 0.6872 (4) | 0.9767 (4) | 1.0032 (3) | 0.0983 (12) | |
H9 | 0.6744 | 0.9918 | 1.0664 | 0.118* | |
C10 | 0.8156 (5) | 1.0368 (4) | 1.0004 (4) | 0.1048 (14) | |
H10 | 0.8906 | 1.0919 | 1.0620 | 0.126* | |
C11 | 0.8344 (4) | 1.0165 (3) | 0.9078 (4) | 0.0948 (12) | |
H11 | 0.9210 | 1.0600 | 0.9053 | 0.114* | |
C12 | 0.7251 (3) | 0.9314 (3) | 0.8169 (3) | 0.0674 (8) | |
H12 | 0.7392 | 0.9164 | 0.7543 | 0.081* | |
C13 | 0.2449 (3) | 0.7812 (2) | 0.68571 (19) | 0.0440 (5) | |
C14 | 0.1186 (3) | 0.6945 (3) | 0.6742 (2) | 0.0599 (7) | |
H14 | 0.1095 | 0.6145 | 0.6664 | 0.072* | |
C15 | 0.0051 (3) | 0.7254 (3) | 0.6740 (3) | 0.0766 (10) | |
H15 | −0.0796 | 0.6662 | 0.6670 | 0.092* | |
C16 | 0.0169 (4) | 0.8421 (4) | 0.6842 (3) | 0.0864 (11) | |
H16 | −0.0596 | 0.8627 | 0.6842 | 0.104* | |
C17 | 0.1409 (4) | 0.9288 (3) | 0.6946 (3) | 0.0919 (11) | |
H17 | 0.1481 | 1.0084 | 0.7004 | 0.110* | |
C18 | 0.2562 (3) | 0.8991 (3) | 0.6965 (3) | 0.0682 (8) | |
H18 | 0.3413 | 0.9589 | 0.7052 | 0.082* | |
N1 | 0.4496 (3) | 0.2959 (2) | 0.6888 (2) | 0.0679 (7) | |
C19 | 0.5859 (4) | 0.3255 (3) | 0.7008 (3) | 0.0828 (10) | |
H19 | 0.6074 | 0.3413 | 0.6415 | 0.099* | |
C20 | 0.6939 (4) | 0.3328 (3) | 0.7980 (3) | 0.0821 (10) | |
H20 | 0.7875 | 0.3522 | 0.8038 | 0.099* | |
C21 | 0.6661 (4) | 0.3118 (3) | 0.8881 (3) | 0.0710 (9) | |
C22 | 0.5253 (4) | 0.2827 (3) | 0.8729 (3) | 0.0803 (10) | |
H22 | 0.5021 | 0.2682 | 0.9316 | 0.096* | |
C23 | 0.4188 (3) | 0.2743 (3) | 0.7750 (3) | 0.0721 (9) | |
H23 | 0.3243 | 0.2536 | 0.7673 | 0.087* | |
C24 | 0.3343 (4) | 0.2913 (4) | 0.5839 (3) | 0.1027 (13) | |
H24A | 0.2440 | 0.2685 | 0.5899 | 0.154* | 0.50 |
H24B | 0.3278 | 0.2335 | 0.5275 | 0.154* | 0.50 |
H24C | 0.3560 | 0.3688 | 0.5658 | 0.154* | 0.50 |
H24D | 0.3746 | 0.3121 | 0.5323 | 0.154* | 0.50 |
H24E | 0.2908 | 0.3470 | 0.5946 | 0.154* | 0.50 |
H24F | 0.2625 | 0.2117 | 0.5564 | 0.154* | 0.50 |
C25 | 0.7837 (4) | 0.3268 (4) | 0.9976 (3) | 0.1086 (14) | |
H25A | 0.8741 | 0.3471 | 0.9918 | 0.163* | 0.50 |
H25B | 0.7638 | 0.2533 | 1.0227 | 0.163* | 0.50 |
H25C | 0.7888 | 0.3898 | 1.0485 | 0.163* | 0.50 |
H25D | 0.7437 | 0.3130 | 1.0502 | 0.163* | 0.50 |
H25E | 0.8540 | 0.4068 | 1.0193 | 0.163* | 0.50 |
H25F | 0.8290 | 0.2703 | 0.9935 | 0.163* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sb1 | 0.03565 (9) | 0.04249 (9) | 0.03964 (9) | 0.01453 (7) | 0.01356 (7) | 0.01475 (6) |
S1 | 0.0380 (3) | 0.0684 (5) | 0.0594 (4) | 0.0111 (3) | 0.0151 (3) | 0.0359 (4) |
S2 | 0.0571 (4) | 0.0469 (4) | 0.0451 (4) | 0.0243 (3) | 0.0091 (3) | 0.0097 (3) |
C1 | 0.0406 (14) | 0.0608 (16) | 0.0457 (14) | 0.0226 (12) | 0.0171 (12) | 0.0246 (12) |
C2 | 0.0419 (13) | 0.0511 (15) | 0.0411 (13) | 0.0206 (12) | 0.0133 (11) | 0.0149 (11) |
S3 | 0.0525 (4) | 0.0611 (5) | 0.0796 (5) | 0.0207 (4) | 0.0148 (4) | 0.0387 (4) |
S4 | 0.0422 (4) | 0.0553 (4) | 0.0625 (4) | 0.0165 (3) | 0.0059 (3) | 0.0140 (3) |
C3 | 0.0464 (16) | 0.0633 (18) | 0.0697 (19) | 0.0254 (14) | 0.0160 (14) | 0.0212 (15) |
O1 | 0.0552 (13) | 0.0828 (16) | 0.1117 (19) | 0.0404 (12) | 0.0088 (13) | 0.0294 (14) |
S5 | 0.0407 (3) | 0.0559 (4) | 0.0566 (4) | 0.0171 (3) | 0.0189 (3) | 0.0287 (3) |
S6 | 0.0582 (4) | 0.0930 (6) | 0.0435 (4) | 0.0457 (4) | 0.0229 (3) | 0.0234 (4) |
C4 | 0.0414 (13) | 0.0475 (14) | 0.0451 (14) | 0.0192 (11) | 0.0118 (11) | 0.0188 (11) |
C5 | 0.0434 (14) | 0.0590 (16) | 0.0434 (14) | 0.0262 (12) | 0.0144 (11) | 0.0167 (12) |
S7 | 0.0552 (4) | 0.0962 (6) | 0.0494 (4) | 0.0334 (4) | 0.0213 (3) | 0.0338 (4) |
S8 | 0.0431 (4) | 0.0945 (6) | 0.0560 (4) | 0.0309 (4) | 0.0168 (3) | 0.0249 (4) |
C6 | 0.0529 (18) | 0.092 (2) | 0.0546 (18) | 0.0288 (17) | 0.0128 (15) | 0.0220 (16) |
O2 | 0.0614 (14) | 0.168 (3) | 0.0549 (13) | 0.0478 (16) | 0.0073 (11) | 0.0302 (15) |
C7 | 0.0394 (14) | 0.0444 (14) | 0.0534 (16) | 0.0121 (11) | 0.0118 (12) | 0.0142 (12) |
C8 | 0.0612 (19) | 0.071 (2) | 0.064 (2) | 0.0144 (16) | 0.0177 (16) | −0.0013 (16) |
C9 | 0.096 (3) | 0.094 (3) | 0.068 (2) | 0.022 (2) | 0.013 (2) | −0.019 (2) |
C10 | 0.083 (3) | 0.077 (3) | 0.091 (3) | 0.011 (2) | −0.009 (2) | −0.017 (2) |
C11 | 0.0484 (19) | 0.073 (2) | 0.120 (3) | −0.0013 (17) | 0.009 (2) | 0.018 (2) |
C12 | 0.0470 (17) | 0.069 (2) | 0.072 (2) | 0.0122 (15) | 0.0164 (15) | 0.0228 (16) |
C13 | 0.0399 (13) | 0.0452 (14) | 0.0427 (13) | 0.0156 (11) | 0.0135 (11) | 0.0074 (11) |
C14 | 0.0486 (16) | 0.0534 (17) | 0.077 (2) | 0.0152 (13) | 0.0293 (15) | 0.0076 (14) |
C15 | 0.0458 (18) | 0.097 (3) | 0.078 (2) | 0.0166 (18) | 0.0280 (17) | −0.0033 (19) |
C16 | 0.059 (2) | 0.119 (3) | 0.079 (2) | 0.049 (2) | 0.0196 (18) | −0.009 (2) |
C17 | 0.089 (3) | 0.072 (2) | 0.120 (3) | 0.050 (2) | 0.036 (2) | 0.003 (2) |
C18 | 0.0570 (18) | 0.0543 (18) | 0.088 (2) | 0.0220 (15) | 0.0252 (17) | 0.0063 (16) |
N1 | 0.0670 (17) | 0.0765 (17) | 0.0613 (16) | 0.0292 (14) | 0.0270 (14) | 0.0083 (13) |
C19 | 0.083 (3) | 0.111 (3) | 0.075 (2) | 0.044 (2) | 0.048 (2) | 0.015 (2) |
C20 | 0.062 (2) | 0.108 (3) | 0.089 (3) | 0.039 (2) | 0.040 (2) | 0.012 (2) |
C21 | 0.069 (2) | 0.083 (2) | 0.077 (2) | 0.0455 (19) | 0.0338 (18) | 0.0186 (18) |
C22 | 0.081 (2) | 0.112 (3) | 0.079 (2) | 0.053 (2) | 0.047 (2) | 0.043 (2) |
C23 | 0.0535 (18) | 0.086 (2) | 0.088 (2) | 0.0271 (17) | 0.0386 (18) | 0.0251 (19) |
C24 | 0.096 (3) | 0.135 (4) | 0.062 (2) | 0.051 (3) | 0.013 (2) | 0.009 (2) |
C25 | 0.094 (3) | 0.147 (4) | 0.098 (3) | 0.077 (3) | 0.026 (2) | 0.037 (3) |
Geometric parameters (Å, º) top
Sb1—C7 | 2.163 (3) | C13—C18 | 1.376 (4) |
Sb1—C13 | 2.165 (2) | C14—C15 | 1.381 (4) |
Sb1—S1 | 2.5376 (6) | C14—H14 | 0.9300 |
Sb1—S5 | 2.5561 (6) | C15—C16 | 1.360 (5) |
Sb1—S2 | 2.5929 (7) | C15—H15 | 0.9300 |
Sb1—S6 | 2.6081 (7) | C16—C17 | 1.362 (5) |
S1—C1 | 1.744 (2) | C16—H16 | 0.9300 |
S2—C2 | 1.731 (2) | C17—C18 | 1.385 (4) |
C1—C2 | 1.355 (3) | C17—H17 | 0.9300 |
C1—S3 | 1.753 (3) | C18—H18 | 0.9300 |
C2—S4 | 1.749 (2) | N1—C19 | 1.337 (4) |
S3—C3 | 1.764 (3) | N1—C23 | 1.348 (4) |
S4—C3 | 1.756 (3) | N1—C24 | 1.475 (4) |
C3—O1 | 1.212 (3) | C19—C20 | 1.362 (4) |
S5—C4 | 1.746 (2) | C19—H19 | 0.9300 |
S6—C5 | 1.729 (2) | C20—C21 | 1.382 (4) |
C4—C5 | 1.359 (3) | C20—H20 | 0.9300 |
C4—S7 | 1.748 (2) | C21—C22 | 1.371 (4) |
C5—S8 | 1.746 (2) | C21—C25 | 1.494 (4) |
S7—C6 | 1.768 (3) | C22—C23 | 1.358 (4) |
S8—C6 | 1.766 (3) | C22—H22 | 0.9300 |
C6—O2 | 1.209 (3) | C23—H23 | 0.9300 |
C7—C8 | 1.374 (4) | C24—H24A | 0.9600 |
C7—C12 | 1.381 (4) | C24—H24B | 0.9600 |
C8—C9 | 1.389 (4) | C24—H24C | 0.9600 |
C8—H8 | 0.9300 | C24—H24D | 0.9600 |
C9—C10 | 1.360 (5) | C24—H24E | 0.9600 |
C9—H9 | 0.9300 | C24—H24F | 0.9600 |
C10—C11 | 1.360 (5) | C25—H25A | 0.9600 |
C10—H10 | 0.9300 | C25—H25B | 0.9600 |
C11—C12 | 1.387 (5) | C25—H25C | 0.9600 |
C11—H11 | 0.9300 | C25—H25D | 0.9600 |
C12—H12 | 0.9300 | C25—H25E | 0.9600 |
C13—C14 | 1.375 (3) | C25—H25F | 0.9600 |
| | | |
C7—Sb1—C13 | 98.25 (9) | C15—C16—H16 | 120.0 |
C7—Sb1—S1 | 92.69 (7) | C17—C16—H16 | 120.0 |
C13—Sb1—S1 | 94.08 (7) | C16—C17—C18 | 120.4 (3) |
C7—Sb1—S5 | 93.13 (7) | C16—C17—H17 | 119.8 |
C13—Sb1—S5 | 94.26 (7) | C18—C17—H17 | 119.8 |
S1—Sb1—S5 | 169.05 (3) | C13—C18—C17 | 120.0 (3) |
C7—Sb1—S2 | 169.47 (7) | C13—C18—H18 | 120.0 |
C13—Sb1—S2 | 89.91 (7) | C17—C18—H18 | 120.0 |
S1—Sb1—S2 | 80.03 (2) | C19—N1—C23 | 119.4 (3) |
S5—Sb1—S2 | 92.89 (2) | C19—N1—C24 | 120.8 (3) |
C7—Sb1—S6 | 90.82 (7) | C23—N1—C24 | 119.8 (3) |
C13—Sb1—S6 | 169.12 (7) | N1—C19—C20 | 121.3 (3) |
S1—Sb1—S6 | 91.48 (2) | N1—C19—H19 | 119.4 |
S5—Sb1—S6 | 79.17 (2) | C20—C19—H19 | 119.4 |
S2—Sb1—S6 | 81.83 (2) | C19—C20—C21 | 120.8 (3) |
C1—S1—Sb1 | 93.54 (8) | C19—C20—H20 | 119.6 |
C2—S2—Sb1 | 92.58 (9) | C21—C20—H20 | 119.6 |
C2—C1—S1 | 124.24 (19) | C22—C21—C20 | 116.2 (3) |
C2—C1—S3 | 116.66 (19) | C22—C21—C25 | 121.8 (3) |
S1—C1—S3 | 118.76 (15) | C20—C21—C25 | 122.0 (3) |
C1—C2—S2 | 123.81 (19) | C23—C22—C21 | 122.2 (3) |
C1—C2—S4 | 116.72 (19) | C23—C22—H22 | 118.9 |
S2—C2—S4 | 119.20 (14) | C21—C22—H22 | 118.9 |
C1—S3—C3 | 96.89 (13) | N1—C23—C22 | 120.1 (3) |
C2—S4—C3 | 97.18 (12) | N1—C23—H23 | 119.9 |
O1—C3—S4 | 124.1 (2) | C22—C23—H23 | 119.9 |
O1—C3—S3 | 123.4 (2) | N1—C24—H24A | 109.5 |
S4—C3—S3 | 112.54 (16) | N1—C24—H24B | 109.5 |
C4—S5—Sb1 | 93.32 (8) | H24A—C24—H24B | 109.5 |
C5—S6—Sb1 | 92.66 (9) | N1—C24—H24C | 109.5 |
C5—C4—S5 | 123.83 (19) | H24A—C24—H24C | 109.5 |
C5—C4—S7 | 116.64 (19) | H24B—C24—H24C | 109.5 |
S5—C4—S7 | 119.20 (14) | N1—C24—H24D | 109.5 |
C4—C5—S6 | 123.74 (19) | H24A—C24—H24D | 141.1 |
C4—C5—S8 | 116.78 (19) | H24B—C24—H24D | 56.3 |
S6—C5—S8 | 119.12 (14) | H24C—C24—H24D | 56.3 |
C4—S7—C6 | 97.27 (13) | N1—C24—H24E | 109.5 |
C5—S8—C6 | 97.33 (13) | H24A—C24—H24E | 56.3 |
O2—C6—S8 | 123.7 (2) | H24B—C24—H24E | 141.1 |
O2—C6—S7 | 124.3 (2) | H24C—C24—H24E | 56.3 |
S8—C6—S7 | 111.93 (16) | H24D—C24—H24E | 109.5 |
C8—C7—C12 | 119.7 (3) | N1—C24—H24F | 109.5 |
C8—C7—Sb1 | 118.9 (2) | H24A—C24—H24F | 56.3 |
C12—C7—Sb1 | 121.4 (2) | H24B—C24—H24F | 56.3 |
C7—C8—C9 | 119.6 (3) | H24C—C24—H24F | 141.1 |
C7—C8—H8 | 120.2 | H24D—C24—H24F | 109.5 |
C9—C8—H8 | 120.2 | H24E—C24—H24F | 109.5 |
C10—C9—C8 | 120.5 (4) | C21—C25—H25A | 109.5 |
C10—C9—H9 | 119.8 | C21—C25—H25B | 109.5 |
C8—C9—H9 | 119.8 | H25A—C25—H25B | 109.5 |
C11—C10—C9 | 120.1 (4) | C21—C25—H25C | 109.5 |
C11—C10—H10 | 120.0 | H25A—C25—H25C | 109.5 |
C9—C10—H10 | 120.0 | H25B—C25—H25C | 109.5 |
C10—C11—C12 | 120.4 (4) | C21—C25—H25D | 109.5 |
C10—C11—H11 | 119.8 | H25A—C25—H25D | 141.1 |
C12—C11—H11 | 119.8 | H25B—C25—H25D | 56.3 |
C7—C12—C11 | 119.6 (3) | H25C—C25—H25D | 56.3 |
C7—C12—H12 | 120.2 | C21—C25—H25E | 109.5 |
C11—C12—H12 | 120.2 | H25A—C25—H25E | 56.3 |
C14—C13—C18 | 119.0 (3) | H25B—C25—H25E | 141.1 |
C14—C13—Sb1 | 121.0 (2) | H25C—C25—H25E | 56.3 |
C18—C13—Sb1 | 120.05 (19) | H25D—C25—H25E | 109.5 |
C13—C14—C15 | 120.5 (3) | C21—C25—H25F | 109.5 |
C13—C14—H14 | 119.7 | H25A—C25—H25F | 56.3 |
C15—C14—H14 | 119.7 | H25B—C25—H25F | 56.3 |
C16—C15—C14 | 120.1 (3) | H25C—C25—H25F | 141.1 |
C16—C15—H15 | 119.9 | H25D—C25—H25F | 109.5 |
C14—C15—H15 | 119.9 | H25E—C25—H25F | 109.5 |
C15—C16—C17 | 120.0 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···O1i | 0.93 | 2.46 | 3.336 (4) | 158 |
C23—H23···O1ii | 0.93 | 2.28 | 3.204 (4) | 173 |
C24—H24D···S6iii | 0.96 | 2.87 | 3.790 (4) | 162 |
C25—H25A···O2iv | 0.96 | 2.54 | 3.457 (4) | 159 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+2, −y+1, −z+2. |
Coordination of Sb (Å, °) in (IV), (IIIa) and (IIIb) top | (IV) | (IIIa) | (IIIb) |
Sb1-S1 | 2.5376 (6) | 2.5569 (11) | 2.5404 (14) |
Sb1-S2 | 2.5929 (7) | 2.6083 (11) | 2.6277 (15) |
Sb1-S5 | 2.5561 (6) | 2.5291 (10) | 2.5339 (14) |
Sb1-S6 | 2.6081 (7) | 2.5771 (11) | 2.6404 (14) |
Sb1-C7 | 2.163 (3) | 2.153 (3) | 2.158 (5) |
Sb1-C13 | 2.165 (2) | 2.165 (3) | 2.170 (5) |
S1-Sb1-S2 | 80.03 (2) | 79.25 (4) | 80.11 (5) |
S1-Sb1-S5 | 169.05 (3) | 171.39 (4) | 166.88 (5) |
S1-Sb1-S6 | 91.48 (2) | 92.36 (4) | 89.69 (5) |
S1-Sb1_C7 | 92.69 (7) | 92.46 (10) | 92.46 (13) |
S1-Sb1-C13 | 94.08 (7) | 91.55 (9) | 96.83 (14) |
S2-Sb1-S5 | 92.89 (2) | 94.70 (3) | 90.69 (5) |
S2-Sb1-S6 | 81.83 (2) | 80.71 (3) | 86.30 (5) |
S2-Sb1-C7 | 169.47 (7) | 169.00 (11) | 171.97 (14) |
S2-Sb1-C13 | 89.91 (7) | 89.52 (9) | 89.74 (14) |
S5-Sb1-S6 | 79.17 (2) | 80.55 (4) | 80.33 (5) |
S5-Sb1-C7 | 93.13 (7) | 92.72 (10) | 96.14 (13) |
S5-Sb1-C13 | 94.26 (7) | 94.54 (9) | 92.42 (14) |
S6-Sb1-C7 | 90.82 (7) | 92.52 (10) | 90.67 (14) |
S6-Sb1-C13 | 169.12 (7) | 168.61 (9) | 171.68 (14) |
C7-Sb1-C13 | 98.25 (9) | 98.00 (12) | 94.18 (19) |
Sb1-S1-C1 | 93.54 (8) | 93.44 (13) | 96.30 (19) |
Sb1-S2-C2 | 92.58 (9) | 92.89 (13) | 94.54 (19) |
Sb1-S5-C4 | 93.28 (8) | 93.04 (12) | 97.52 (18) |
Sb1-S6-C5 | 92.66 (9) | 92.46 (12) | 95.18 (19) |
O1-Sb1-O2 | 177.93 (3) | 179.24 (4) | 66.29 (6) |
Twist | 67.67 (3) | 71.51 (5) | 10.43 (8) |
Notes: Bond and angle designations wholly consistant with Fig. 1 extended
to bonds and angles of corresponding type in columns 2 and 3. Twist is the
dihedral angle between the ligand planes defined, as noted in the text,
by the C═C bond and the four S atoms associated with it. |
Bond lengths and angles (Å, °) for the dmio ligands in (IV), (IIIa) and
(IIIb) top | (IV) | | (IIIa) | | (IIIb) | |
| Lig 1 | Lig 2 | Lig 1 | Lig 2 | Lig 1 | Lig 2 |
S1-C1 | 1.744 (2) | 1.746 (2) | 1.742 (4) | 1.747 (4) | 1.737 (6) | 1.733 (5) |
S2-C2 | 1.731 (2) | 1.729 (2) | 1.732 (4) | 1.732 (4) | 1.712 (6) | 1.726 (6) |
C1-C2 | 1.355 (3) | 1.359 (3) | 1.347 (5) | 1.352 (5) | 1.366 (8) | 1.349 (7) |
C1-S3 | 1.753 (3) | 1.748 (2) | 1.745 (4) | 1.749 (4) | 1.744 (6) | 1.743 (5) |
C2-S4 | 1.749 (2) | 1.746 (2) | 1.751 (4) | 1.742 (4) | 1.748 (6) | 1.756 (6) |
S3-C3 | 1.764 (3) | 1.768 (3) | 1.767 (5) | 1.771 (4) | 1.765 (7) | 1.768 (7) |
S4-C3 | 1.756 (3) | 1.766 (3) | 1.762 (5) | 1.760 (5) | 1.768 (7) | 1.757 (7) |
C3-O1 | 1.212 (3) | 1.209 (3) | 1.210 (4) | 1.210 (4) | 1.213 (7) | 1.212 (7) |
C3oop | 0.054 (3) | 0.045 (4) | -0.136 (4) | 0.055 (4) | 0.092 (7) | -0.101 (7) |
O1oop | 0.092 (3) | 0.034 (3) | -0.247 (4) | 0.084 (3) | 0.169 (5) | -0.195 (5) |
Sb1oop | 1.5944 (9) | 1.6447 (10) | -1.6484 (2) | 1.5893 (2) | 1.4819 (3) | -1.4056 (3) |
C2-C1-S1 | 124.24 (19) | 123.83 (19) | 124.0 (3) | 124.3 (3) | 124.4 (4) | 125.1 (4) |
C2-C1-S3 | 116.66 (19) | 116.64 (19) | 117.0 (3) | 116.8 (3) | 117.5 (4) | 117.4 (4) |
S1-C1-S3 | 118.76 (15) | 119.20 (14) | 118.5 (2) | 118.4 (2) | 117.7 (3) | 117.1 (3) |
C1-C2-S2 | 123.81 (19) | 123.74 (19) | 124.2 (3) | 123.9 (3) | 124.9 (4) | 125.1 (4) |
C1-C2-S4 | 116.72 (19) | 116.78 (19) | 116.8 (3) | 117.0 (3) | 115.6 (4) | 116.1 (4) |
S2-C2-S4 | 119.20 (14) | 119.12 (14) | 118.4 (2) | 118.9 (2) | 119.1 (3) | 118.4 (3) |
C1-S3-C3 | 96.89 (13) | 97.27 (13) | 96.86 (19) | 96.71 (19) | 97.1 (3) | 97.1 (3) |
C2-S4-C3 | 97.18 (12) | 97.33 (13) | 96.88 (19) | 97.15 (19) | 97.7 (3) | 97.5 (3) |
O1-C3-S3 | 123.4 (2) | 124.3 (2) | 124.1 (4) | 123.5 (4) | 124.3 (6) | 123.2 (6) |
O1-C3-S4 | 124.1 (2) | 123.7 (2) | 123.6 (4) | 124.2 (3) | 123.7 (6) | 124.8 (6) |
S4-C3-S3 | 112.54 (16) | 111.93 (16) | 112.3 (2) | 112.3 (2) | 112.0 (3) | 112.0 (3) |
Notes: Bond and angle designations wholly consistant with the ligand shown
in Fig. 1 extended to bonds and angles of corresponding type in the
remaining columns. |
Geometry (Å, °) of weak hydrogen-bond contacts in (IV) top | C-H | H···A | C···A | C-H···A |
C17-H17···O1i | 0.93 | 2.46 | 3.336 (4) | 158 |
C23-H23···O1ii | 0.93 | 2.28 | 3.204 (4) | 172 |
C25-H25A···O2iii | 0.96 | 2.54 | 3.457 (4) | 159 |
C24-H24D···S6vi | 0.96 | 2.87 | 3.790 (4) | 162 |
Symmetry codes: (vi) 1-x, 1-y, 1-z, and the remainder as in the caption of
Fig. 2. |
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