Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102018712/lc0053sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018712/lc0053sup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768102018712/lc0053sup3.pdf |
CCDC reference: 201622
Data collection: Bruker SMART; cell refinement: Bruker SMART; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: Koritsanszky et al., (1999); molecular graphics: Koritsanszky et al., (1999); software used to prepare material for publication: Koritsanszky et al., (1999).
C9H6OS | Dx = 1.481 Mg m−3 |
Mr = 162.21 | Melting point: 371 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 9651 reflections |
a = 4.0515 (2) Å | θ = 2.3–50.1° |
b = 10.1749 (7) Å | µ = 0.37 mm−1 |
c = 17.6519 (9) Å | T = 90 K |
V = 727.67 (7) Å3 | Prism, yellow |
Z = 4 | 0.60 × 0.37 × 0.10 mm |
F(000) = 336 |
CCD area detector Bruker Axs SMART APEX diffractometer | 6908 reflections with I > 2σ(I) |
ϕ and ω scans | Rint = 0.038 |
Absorption correction: empirical (using intensity measurements) R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | θmax = 50.1°, θmin = 2.3° |
Tmin = 0.809, Tmax = 0.964 | h = 0→8 |
7608 measured reflections | k = 0→21 |
7608 independent reflections | l = −37→37 |
Refinement on F | All H-atom parameters refined |
Least-squares matrix: full | w = 1/[σ2(Fo2)] |
R[F2 > 2σ(F2)] = 0.022 | (Δ/σ)max = 0.002 |
wR(F2) = 0.022 | Δρmax = 0.20 e Å−3 |
S = 1.81 | Δρmin = −0.28 e Å−3 |
7608 reflections | Absolute structure: Flack H.D. (1983), Acta Cryst. A39, 876-881 |
318 parameters | Absolute structure parameter: −0.01 (3) |
0 restraints |
C9H6OS | V = 727.67 (7) Å3 |
Mr = 162.21 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 4.0515 (2) Å | µ = 0.37 mm−1 |
b = 10.1749 (7) Å | T = 90 K |
c = 17.6519 (9) Å | 0.60 × 0.37 × 0.10 mm |
CCD area detector Bruker Axs SMART APEX diffractometer | 7608 independent reflections |
Absorption correction: empirical (using intensity measurements) R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 6908 reflections with I > 2σ(I) |
Tmin = 0.809, Tmax = 0.964 | Rint = 0.038 |
7608 measured reflections |
R[F2 > 2σ(F2)] = 0.022 | All H-atom parameters refined |
wR(F2) = 0.022 | Δρmax = 0.20 e Å−3 |
S = 1.81 | Δρmin = −0.28 e Å−3 |
7608 reflections | Absolute structure: Flack H.D. (1983), Acta Cryst. A39, 876-881 |
318 parameters | Absolute structure parameter: −0.01 (3) |
0 restraints |
Experimental. Crystal to Detector distance was 6.03 cm, ω range is 0.3 ° and exposure time was 15 s, 30 s and 45 s in three batches respectively. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S(1) | 0.51603 (3) | 0.94025 (1) | 0.83667 (1) | 0.016 | |
O(1) | 0.23422 (13) | 1.01214 (4) | 0.71198 (3) | 0.013 | |
C(8) | 0.05056 (10) | 0.99619 (4) | 0.64708 (2) | 0.012 | |
C(3) | 0.03656 (11) | 0.76104 (4) | 0.66970 (2) | 0.014 | |
C(9) | −0.06119 (10) | 0.87198 (4) | 0.62490 (2) | 0.013 | |
C(2) | 0.22833 (12) | 0.77913 (4) | 0.73200 (2) | 0.014 | |
C(4) | −0.25394 (11) | 0.86232 (5) | 0.55854 (3) | 0.016 | |
C(1) | 0.31873 (10) | 0.90866 (4) | 0.75672 (2) | 0.012 | |
C(7) | −0.01552 (12) | 1.10918 (4) | 0.60496 (2) | 0.015 | |
C(6) | −0.20365 (13) | 1.09660 (5) | 0.53942 (3) | 0.017 | |
C(5) | −0.32431 (12) | 0.97352 (5) | 0.51619 (3) | 0.018 | |
H(3) | −0.02857 | 0.66100 | 0.65575 | 0.038 (4) | |
H(7) | 0.08128 | 1.20440 | 0.62037 | 0.046 (4) | |
H(4) | −0.36004 | 0.76764 | 0.54542 | 0.069 (5) | |
H(5) | −0.49509 | 0.96935 | 0.46927 | 0.046 (5) | |
H(6) | −0.26079 | 1.18565 | 0.50882 | 0.042 (4) | |
H(2) | 0.32209 | 0.69667 | 0.76395 | 0.031 (4) | |
DUM0 | 0.00000 | 0.00000 | 0.00000 | 0.000 | 0.0000 |
U11 | U22 | U33 | U12 | U13 | U23 | |
S(1) | 0.01815 (5) | 0.01430 (4) | 0.01659 (4) | −0.00002 (3) | −0.00450 (3) | −0.00010 (3) |
O(1) | 0.0157 (1) | 0.0100 (1) | 0.0139 (1) | −0.0010 (1) | −0.0007 (1) | 0.0002 (1) |
C(8) | 0.0125 (1) | 0.0107 (1) | 0.0126 (1) | −0.0002 (1) | 0.0015 (1) | 0.0000 (1) |
C(3) | 0.0169 (1) | 0.0105 (1) | 0.0155 (1) | −0.0019 (1) | 0.0014 (1) | −0.0014 (1) |
C(9) | 0.0126 (1) | 0.0121 (1) | 0.0131 (1) | −0.0010 (1) | 0.0019 (1) | −0.0013 (1) |
C(2) | 0.0175 (2) | 0.0101 (1) | 0.0153 (1) | −0.0005 (1) | 0.0007 (1) | 0.0006 (1) |
C(4) | 0.0145 (1) | 0.0182 (2) | 0.0144 (1) | −0.0013 (1) | 0.0009 (1) | −0.0030 (1) |
C(1) | 0.0129 (1) | 0.0109 (1) | 0.0134 (1) | −0.0003 (1) | 0.0003 (1) | 0.0000 (1) |
C(7) | 0.0167 (1) | 0.0130 (1) | 0.0146 (1) | 0.0007 (1) | 0.0013 (1) | 0.0016 (1) |
C(6) | 0.0180 (2) | 0.0193 (2) | 0.0147 (2) | 0.0019 (1) | 0.0007 (1) | 0.0029 (1) |
C(5) | 0.0165 (2) | 0.0231 (2) | 0.0137 (1) | 0.0001 (2) | 0.0000 (1) | −0.0002 (1) |
S(1)—C(1) | 1.6534 (4) | C(2)—C(1) | 1.4358 (6) |
O(1)—C(8) | 1.3757 (6) | C(2)—H(2) | 1.0800 |
O(1)—C(1) | 1.3601 (6) | C(4)—C(5) | 1.3858 (7) |
C(8)—C(9) | 1.3984 (5) | C(4)—H(4) | 1.0800 |
C(8)—C(7) | 1.3951 (5) | C(7)—C(6) | 1.3913 (7) |
C(3)—C(9) | 1.4341 (6) | C(7)—H(7) | 1.0800 |
C(3)—C(2) | 1.3590 (6) | C(6)—C(5) | 1.4054 (7) |
C(3)—H(3) | 1.0800 | C(6)—H(6) | 1.0800 |
C(9)—C(4) | 1.4112 (6) | C(5)—H(5) | 1.0800 |
C(8)—O(1)—C(1) | 121.90 (4) | C(9)—C(4)—H(4) | 117.41 |
O(1)—C(8)—C(9) | 120.99 (4) | C(5)—C(4)—H(4) | 122.06 |
O(1)—C(8)—C(7) | 116.77 (4) | S(1)—C(1)—O(1) | 117.83 (3) |
C(9)—C(8)—C(7) | 122.24 (4) | S(1)—C(1)—C(2) | 124.14 (3) |
C(9)—C(3)—C(2) | 119.84 (4) | O(1)—C(1)—C(2) | 118.03 (4) |
C(9)—C(3)—H(3) | 123.28 | C(8)—C(7)—C(6) | 118.19 (4) |
C(2)—C(3)—H(3) | 116.86 | C(8)—C(7)—H(7) | 122.36 |
C(8)—C(9)—C(3) | 117.88 (4) | C(6)—C(7)—H(7) | 119.41 |
C(8)—C(9)—C(4) | 118.33 (4) | C(7)—C(6)—C(5) | 121.01 (4) |
C(3)—C(9)—C(4) | 123.76 (4) | C(7)—C(6)—H(6) | 117.13 |
C(3)—C(2)—C(1) | 121.07 (4) | C(5)—C(6)—H(6) | 121.81 |
C(3)—C(2)—H(2) | 121.23 | C(4)—C(5)—C(6) | 119.90 (5) |
C(1)—C(2)—H(2) | 117.69 | C(4)—C(5)—H(5) | 120.89 |
C(9)—C(4)—C(5) | 120.31 (4) | C(6)—C(5)—H(5) | 118.79 |
C(8)—O(1)—C(1)—S(1) | −175.5 (1) | C(8)—C(9)—C(4)—C(5) | 1.1 (1) |
C(1)—O(1)—C(8)—C(9) | 0.9 (1) | C(8)—C(9)—C(4)—H(4) | −173.6 |
C(8)—O(1)—C(1)—C(2) | 3.8 (1) | C(3)—C(9)—C(4)—C(5) | −176.7 (1) |
C(1)—O(1)—C(8)—C(7) | −178.8 (1) | C(3)—C(9)—C(4)—H(4) | 8.6 |
O(1)—C(8)—C(9)—C(3) | −3.3 (1) | C(3)—C(2)—C(1)—S(1) | 173.1 (1) |
O(1)—C(8)—C(9)—C(4) | 178.8 (1) | C(3)—C(2)—C(1)—O(1) | −6.3 (1) |
O(1)—C(8)—C(7)—C(6) | −179.3 (1) | H(2)—C(2)—C(1)—S(1) | −8.1 |
O(1)—C(8)—C(7)—H(7) | 3.0 | H(2)—C(2)—C(1)—O(1) | 172.5 |
C(7)—C(8)—C(9)—C(3) | 176.4 (1) | C(9)—C(4)—C(5)—C(6) | −0.1 (1) |
C(7)—C(8)—C(9)—C(4) | −1.6 (1) | C(9)—C(4)—C(5)—H(5) | −172.6 |
C(9)—C(8)—C(7)—C(6) | 1.0 (1) | H(4)—C(4)—C(5)—C(6) | 174.4 |
C(9)—C(8)—C(7)—H(7) | −176.7 | H(4)—C(4)—C(5)—H(5) | 1.9 |
C(2)—C(3)—C(9)—C(8) | 0.8 (1) | C(8)—C(7)—C(6)—C(5) | 0.0 (1) |
C(2)—C(3)—C(9)—C(4) | 178.6 (1) | C(8)—C(7)—C(6)—H(6) | 177.5 |
C(9)—C(3)—C(2)—C(1) | 3.9 (1) | H(7)—C(7)—C(6)—C(5) | 177.8 |
C(9)—C(3)—C(2)—H(2) | −174.8 | H(7)—C(7)—C(6)—H(6) | −4.7 |
H(3)—C(3)—C(9)—C(8) | −177.3 | C(7)—C(6)—C(5)—C(4) | −0.5 (1) |
H(3)—C(3)—C(9)—C(4) | 0.5 | C(7)—C(6)—C(5)—H(5) | 172.2 |
H(3)—C(3)—C(2)—C(1) | −177.8 | H(6)—C(6)—C(5)—C(4) | −177.9 |
H(3)—C(3)—C(2)—H(2) | 3.4 | H(6)—C(6)—C(5)—H(5) | −5.2 |
Experimental details
Crystal data | |
Chemical formula | C9H6OS |
Mr | 162.21 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 90 |
a, b, c (Å) | 4.0515 (2), 10.1749 (7), 17.6519 (9) |
V (Å3) | 727.67 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.37 |
Crystal size (mm) | 0.60 × 0.37 × 0.10 |
Data collection | |
Diffractometer | CCD area detector Bruker Axs SMART APEX diffractometer |
Absorption correction | Empirical (using intensity measurements) R.H. Blessing, Acta Cryst. (1995), A51, 33-38 |
Tmin, Tmax | 0.809, 0.964 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7608, 7608, 6908 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 1.080 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.022, 0.022, 1.81 |
No. of reflections | 7608 |
No. of parameters | 318 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.20, −0.28 |
Absolute structure | Flack H.D. (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | −0.01 (3) |
Computer programs: Bruker SMART, Bruker SAINT, SHELXS97 (Sheldrick, 1997), Koritsanszky et al., (1999).
S(1)—C(1) | 1.6534 (4) | C(2)—C(1) | 1.4358 (6) |
O(1)—C(8) | 1.3757 (6) | C(2)—H(2) | 1.0800 |
O(1)—C(1) | 1.3601 (6) | C(4)—C(5) | 1.3858 (7) |
C(8)—C(9) | 1.3984 (5) | C(4)—H(4) | 1.0800 |
C(8)—C(7) | 1.3951 (5) | C(7)—C(6) | 1.3913 (7) |
C(3)—C(9) | 1.4341 (6) | C(7)—H(7) | 1.0800 |
C(3)—C(2) | 1.3590 (6) | C(6)—C(5) | 1.4054 (7) |
C(3)—H(3) | 1.0800 | C(6)—H(6) | 1.0800 |
C(9)—C(4) | 1.4112 (6) | C(5)—H(5) | 1.0800 |
C(8)—O(1)—C(1) | 121.90 (4) | C(9)—C(4)—H(4) | 117.41 |
O(1)—C(8)—C(9) | 120.99 (4) | C(5)—C(4)—H(4) | 122.06 |
O(1)—C(8)—C(7) | 116.77 (4) | S(1)—C(1)—O(1) | 117.83 (3) |
C(9)—C(8)—C(7) | 122.24 (4) | S(1)—C(1)—C(2) | 124.14 (3) |
C(9)—C(3)—C(2) | 119.84 (4) | O(1)—C(1)—C(2) | 118.03 (4) |
C(9)—C(3)—H(3) | 123.28 | C(8)—C(7)—C(6) | 118.19 (4) |
C(2)—C(3)—H(3) | 116.86 | C(8)—C(7)—H(7) | 122.36 |
C(8)—C(9)—C(3) | 117.88 (4) | C(6)—C(7)—H(7) | 119.41 |
C(8)—C(9)—C(4) | 118.33 (4) | C(7)—C(6)—C(5) | 121.01 (4) |
C(3)—C(9)—C(4) | 123.76 (4) | C(7)—C(6)—H(6) | 117.13 |
C(3)—C(2)—C(1) | 121.07 (4) | C(5)—C(6)—H(6) | 121.81 |
C(3)—C(2)—H(2) | 121.23 | C(4)—C(5)—C(6) | 119.90 (5) |
C(1)—C(2)—H(2) | 117.69 | C(4)—C(5)—H(5) | 120.89 |
C(9)—C(4)—C(5) | 120.31 (4) | C(6)—C(5)—H(5) | 118.79 |
C(8)—O(1)—C(1)—S(1) | −175.5 (1) | C(8)—C(9)—C(4)—C(5) | 1.1 (1) |
C(1)—O(1)—C(8)—C(9) | 0.9 (1) | C(8)—C(9)—C(4)—H(4) | −173.6 |
C(8)—O(1)—C(1)—C(2) | 3.8 (1) | C(3)—C(9)—C(4)—C(5) | −176.7 (1) |
C(1)—O(1)—C(8)—C(7) | −178.8 (1) | C(3)—C(9)—C(4)—H(4) | 8.6 |
O(1)—C(8)—C(9)—C(3) | −3.3 (1) | C(3)—C(2)—C(1)—S(1) | 173.1 (1) |
O(1)—C(8)—C(9)—C(4) | 178.8 (1) | C(3)—C(2)—C(1)—O(1) | −6.3 (1) |
O(1)—C(8)—C(7)—C(6) | −179.3 (1) | H(2)—C(2)—C(1)—S(1) | −8.1 |
O(1)—C(8)—C(7)—H(7) | 3.0 | H(2)—C(2)—C(1)—O(1) | 172.5 |
C(7)—C(8)—C(9)—C(3) | 176.4 (1) | C(9)—C(4)—C(5)—C(6) | −0.1 (1) |
C(7)—C(8)—C(9)—C(4) | −1.6 (1) | C(9)—C(4)—C(5)—H(5) | −172.6 |
C(9)—C(8)—C(7)—C(6) | 1.0 (1) | H(4)—C(4)—C(5)—C(6) | 174.4 |
C(9)—C(8)—C(7)—H(7) | −176.7 | H(4)—C(4)—C(5)—H(5) | 1.9 |
C(2)—C(3)—C(9)—C(8) | 0.8 (1) | C(8)—C(7)—C(6)—C(5) | 0.0 (1) |
C(2)—C(3)—C(9)—C(4) | 178.6 (1) | C(8)—C(7)—C(6)—H(6) | 177.5 |
C(9)—C(3)—C(2)—C(1) | 3.9 (1) | H(7)—C(7)—C(6)—C(5) | 177.8 |
C(9)—C(3)—C(2)—H(2) | −174.8 | H(7)—C(7)—C(6)—H(6) | −4.7 |
H(3)—C(3)—C(9)—C(8) | −177.3 | C(7)—C(6)—C(5)—C(4) | −0.5 (1) |
H(3)—C(3)—C(9)—C(4) | 0.5 | C(7)—C(6)—C(5)—H(5) | 172.2 |
H(3)—C(3)—C(2)—C(1) | −177.8 | H(6)—C(6)—C(5)—C(4) | −177.9 |
H(3)—C(3)—C(2)—H(2) | 3.4 | H(6)—C(6)—C(5)—H(5) | −5.2 |
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