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The title compound, C
15H
13IO
2S, displays an
anti conformation with respect to the olefinic bond. Molecules are linked by weak C—H
O hydrogen bonds.
Supporting information
CCDC reference: 248850
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.005 Å
- R factor = 0.028
- wR factor = 0.076
- Data-to-parameter ratio = 16.1
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
Crystal data top
C15H13IO2S | F(000) = 752.00 |
Mr = 384.23 | Dx = 1.714 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2yn | Cell parameters from 10732 reflections |
a = 8.0171 (3) Å | θ = 2.1–27.4° |
b = 12.3697 (4) Å | µ = 2.29 mm−1 |
c = 15.0866 (5) Å | T = 296 K |
β = 95.685 (1)° | Chunk, yellow |
V = 1488.77 (9) Å3 | 0.40 × 0.40 × 0.25 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2771 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.025 |
ω scans | θmax = 27.4° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −10→10 |
Tmin = 0.414, Tmax = 0.565 | k = −16→16 |
14526 measured reflections | l = −19→19 |
3396 independent reflections | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.028 | w = 1/[0.0009Fo2 + σ(Fo2)]/(4Fo2) |
wR(F2) = 0.076 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.35 e Å−3 |
2771 reflections | Δρmin = −0.78 e Å−3 |
172 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The
weighted R-factor (wR) and goodness of fit (S) are based
on F2. R-factor (gt) are based on 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 | x | y | z | Uiso*/Ueq | |
I(1) | −0.14477 (2) | 0.39239 (1) | 0.26222 (1) | 0.05997 (7) | |
S(1) | 0.28753 (9) | 0.13942 (7) | 0.25764 (4) | 0.0574 (2) | |
O(1) | 0.4475 (3) | 0.1884 (2) | 0.2828 (2) | 0.0796 (7) | |
O(2) | 0.2596 (3) | 0.0848 (2) | 0.1738 (1) | 0.0851 (8) | |
C(1) | 0.1397 (3) | 0.2439 (2) | 0.2671 (2) | 0.0515 (7) | |
C(2) | −0.0050 (3) | 0.2602 (2) | 0.2192 (1) | 0.0444 (6) | |
C(3) | −0.0844 (3) | 0.2026 (2) | 0.1401 (2) | 0.0448 (6) | |
C(4) | −0.0024 (4) | 0.1924 (2) | 0.0635 (2) | 0.0569 (7) | |
C(5) | −0.0796 (5) | 0.1383 (3) | −0.0096 (2) | 0.0706 (9) | |
C(6) | −0.2369 (5) | 0.0941 (2) | −0.0070 (3) | 0.076 (1) | |
C(7) | −0.3194 (5) | 0.1061 (2) | 0.0682 (3) | 0.072 (1) | |
C(8) | −0.2457 (4) | 0.1603 (2) | 0.1414 (2) | 0.0575 (8) | |
C(9) | 0.2420 (3) | 0.0491 (2) | 0.3423 (1) | 0.0475 (6) | |
C(10) | 0.1382 (4) | −0.0387 (3) | 0.3235 (2) | 0.0623 (8) | |
C(11) | 0.1038 (4) | −0.1074 (2) | 0.3914 (3) | 0.073 (1) | |
C(12) | 0.1717 (4) | −0.0892 (3) | 0.4781 (2) | 0.0653 (9) | |
C(13) | 0.2733 (4) | −0.0017 (3) | 0.4953 (2) | 0.0683 (9) | |
C(14) | 0.3109 (4) | 0.0687 (3) | 0.4283 (2) | 0.0598 (8) | |
C(15) | 0.1370 (6) | −0.1656 (3) | 0.5522 (3) | 0.099 (1) | |
H(1) | 0.1683 | 0.2970 | 0.3144 | 0.062* | |
H(4) | 0.1098 | 0.2235 | 0.0625 | 0.069* | |
H(5) | −0.0226 | 0.1316 | −0.0638 | 0.084* | |
H(6) | −0.2897 | 0.0537 | −0.0581 | 0.089* | |
H(7) | −0.4321 | 0.0760 | 0.0700 | 0.085* | |
H(8) | −0.3044 | 0.1697 | 0.1949 | 0.069* | |
H(10) | 0.0900 | −0.0510 | 0.2621 | 0.074* | |
H(11) | 0.0304 | −0.1699 | 0.3780 | 0.088* | |
H(13) | 0.3201 | 0.0127 | 0.5566 | 0.082* | |
H(14) | 0.3848 | 0.1311 | 0.4410 | 0.071* | |
H(151) | 0.0364 | −0.1415 | 0.5785 | 0.122* | |
H(152) | 0.2325 | −0.1664 | 0.5980 | 0.122* | |
H(153) | 0.1187 | −0.2385 | 0.5278 | 0.122* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I(1) | 0.0611 (1) | 0.0512 (1) | 0.0671 (1) | 0.01235 (7) | 0.00381 (9) | −0.00691 (7) |
S(1) | 0.0481 (4) | 0.0764 (5) | 0.0489 (3) | 0.0178 (3) | 0.0102 (3) | 0.0029 (3) |
O(1) | 0.044 (1) | 0.105 (2) | 0.092 (2) | 0.005 (1) | 0.018 (1) | 0.026 (1) |
O(2) | 0.103 (2) | 0.107 (2) | 0.045 (1) | 0.053 (1) | 0.010 (1) | −0.006 (1) |
C(1) | 0.048 (1) | 0.059 (1) | 0.047 (1) | 0.006 (1) | 0.006 (1) | −0.004 (1) |
C(2) | 0.045 (1) | 0.043 (1) | 0.046 (1) | 0.0030 (9) | 0.009 (1) | 0.0033 (9) |
C(3) | 0.047 (1) | 0.041 (1) | 0.046 (1) | 0.0019 (9) | 0.004 (1) | 0.0049 (9) |
C(4) | 0.058 (2) | 0.066 (2) | 0.047 (1) | 0.005 (1) | 0.007 (1) | 0.004 (1) |
C(5) | 0.094 (2) | 0.071 (2) | 0.046 (1) | 0.019 (2) | 0.003 (1) | −0.003 (1) |
C(6) | 0.098 (3) | 0.052 (2) | 0.072 (2) | 0.000 (2) | −0.023 (2) | −0.006 (1) |
C(7) | 0.073 (2) | 0.057 (2) | 0.084 (2) | −0.017 (1) | −0.010 (2) | 0.003 (1) |
C(8) | 0.055 (1) | 0.053 (2) | 0.064 (2) | −0.007 (1) | 0.005 (1) | 0.004 (1) |
C(9) | 0.040 (1) | 0.058 (1) | 0.045 (1) | 0.008 (1) | 0.0041 (9) | −0.006 (1) |
C(10) | 0.057 (2) | 0.065 (2) | 0.063 (2) | 0.000 (1) | −0.002 (1) | −0.016 (1) |
C(11) | 0.059 (2) | 0.059 (2) | 0.101 (3) | −0.005 (1) | 0.013 (2) | −0.009 (2) |
C(12) | 0.060 (2) | 0.062 (2) | 0.077 (2) | 0.015 (1) | 0.025 (2) | 0.008 (1) |
C(13) | 0.071 (2) | 0.083 (2) | 0.050 (1) | 0.004 (2) | 0.003 (1) | −0.002 (1) |
C(14) | 0.062 (2) | 0.065 (2) | 0.051 (1) | −0.006 (1) | −0.004 (1) | −0.005 (1) |
C(15) | 0.096 (3) | 0.095 (3) | 0.114 (3) | 0.021 (2) | 0.050 (3) | 0.035 (2) |
Geometric parameters (Å, º) top
I(1)—C(2) | 2.120 (2) | C(12)—C(13) | 1.364 (5) |
S(1)—O(1) | 1.435 (2) | C(12)—C(15) | 1.511 (6) |
S(1)—O(2) | 1.432 (2) | C(13)—C(14) | 1.388 (4) |
S(1)—C(1) | 1.768 (3) | C(1)—H(1) | 0.9800 |
S(1)—C(9) | 1.762 (3) | C(4)—H(4) | 0.9800 |
C(1)—C(2) | 1.320 (3) | C(5)—H(5) | 0.9800 |
C(2)—C(3) | 1.478 (3) | C(6)—H(6) | 0.9800 |
C(3)—C(4) | 1.390 (4) | C(7)—H(7) | 0.9800 |
C(3)—C(8) | 1.397 (4) | C(8)—H(8) | 0.9800 |
C(4)—C(5) | 1.383 (4) | C(10)—H(10) | 0.9800 |
C(5)—C(6) | 1.378 (6) | C(11)—H(11) | 0.9800 |
C(6)—C(7) | 1.377 (6) | C(13)—H(13) | 0.9800 |
C(7)—C(8) | 1.374 (4) | C(14)—H(14) | 0.9800 |
C(9)—C(10) | 1.381 (4) | C(15)—H(151) | 0.9800 |
C(9)—C(14) | 1.381 (3) | C(15)—H(152) | 0.9800 |
C(10)—C(11) | 1.380 (5) | C(15)—H(153) | 0.9800 |
C(11)—C(12) | 1.384 (5) | | |
| | | |
I1—C2—C1 | 114.4 (2) | C(15)—C(12)—C(13) | 120.4 (3) |
I1—C2—C3 | 114.8 (2) | S(1)—C(1)—H(1) | 115.9832 |
C1—S1—O1 | 105.0 (1) | H(1)—C(1)—C(2) | 115.1622 |
O(2)—S(1)—O(1) | 119.4 (2) | C(3)—C(4)—H(4) | 119.1637 |
C(9)—S(1)—O(1) | 108.6 (1) | C(3)—C(8)—H(8) | 119.1580 |
C1—S1—O2 | 111.6 (1) | H(4)—C(4)—C(5) | 121.1359 |
C9—S1—O2 | 108.4 (1) | C(4)—C(5)—H(5) | 119.8591 |
S1—C1—C2 | 128.9 (2) | H(5)—C(5)—C(6) | 119.6075 |
C9—S1—C1 | 102.5 (1) | C(5)—C(6)—H(6) | 120.3577 |
S(1)—C(9)—C(10) | 120.9 (2) | C(6)—C(7)—H(7) | 120.0192 |
S(1)—C(9)—C(14) | 118.5 (2) | H(6)—C(6)—C(7) | 119.9138 |
C1—C2—C3 | 130.8 (2) | C(7)—C(8)—H(8) | 121.0987 |
C(2)—C(3)—C(8) | 119.6 (2) | H(7)—C(7)—C(8) | 119.2065 |
C(2)—C(3)—C(4) | 120.9 (2) | C(9)—C(10)—H(10) | 119.2968 |
C(8)—C(3)—C(4) | 119.5 (2) | C(9)—C(14)—H(14) | 119.9123 |
C(3)—C(4)—C(5) | 119.7 (3) | H(10)—C(10)—C(11) | 121.1974 |
C(3)—C(8)—C(7) | 119.7 (3) | C(10)—C(11)—H(11) | 119.4872 |
C(4)—C(5)—C(6) | 120.5 (3) | H(11)—C(11)—C(12) | 119.7022 |
C(5)—C(6)—C(7) | 119.7 (3) | C(12)—C(13)—H(13) | 119.2864 |
C(6)—C(7)—C(8) | 120.8 (3) | C(12)—C(15)—H(151) | 109.2255 |
C(14)—C(9)—C(10) | 120.5 (3) | C(12)—C(15)—H(152) | 109.9112 |
C(9)—C(10)—C(11) | 119.5 (3) | C(12)—C(15)—H(153) | 109.2739 |
C(9)—C(14)—C(13) | 118.5 (3) | C(13)—C(14)—H(14) | 121.5437 |
C(10)—C(11)—C(12) | 120.8 (3) | H(13)—C(13)—C(14) | 118.8387 |
C(11)—C(12)—C(13) | 118.7 (3) | H(152)—C(15)—H(151) | 109.4673 |
C(11)—C(12)—C(15) | 120.8 (3) | H(153)—C(15)—H(151) | 109.4735 |
C(12)—C(13)—C(14) | 121.9 (3) | H(153)—C(15)—H(152) | 109.4749 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O2i | 0.98 | 2.48 | 3.342 (4) | 148 |
C8—H8···O1ii | 0.98 | 2.51 | 3.429 (4) | 156 |
Symmetry codes: (i) −x, −y, −z; (ii) x−1, y, z. |
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