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The charge-density distribution in 2H-chromene-2-thione (2-thiocoumarin), C9H6OS, has been determined from X-ray diffraction data measured at 90 K using a CCD detector, to a resolution of sinθ/λ < 1.08 Å−1. A multipolar-atom density model was fitted against 6908 reflections with I > 2σ(I) [R(F) = 0.021, wR(F) = 0.022, goodness of fit = 1.81] in order to generate the difference Fourier maps. The topological properties of the molecular electron density in terms of the bond critical points and the evaluation of the dipole moment show that the molecular dipole moment in the crystal is higher than the corresponding value derived from theoretical calculations.
Supporting information
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).
Crystal data top
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 | |
Data collection top
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 top
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 | |
Crystal data top
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 |
Data collection top
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 | |
Refinement top
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 | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Selected geometric parameters (Å, º) topS(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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