


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808032005/xu2456sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808032005/xu2456Isup2.hkl |
CCDC reference: 709332
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.006 Å
- R factor = 0.049
- wR factor = 0.164
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 -- O5 .. 5.62 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
To an anhydrous pyridine solution (10 ml) of 7-hydroxy-4-methyl-coumarin (1.76 g, 10 mmol), a solution of phenylsulfonyl chloride (11 mmol) was slowly added at 278–283 K with stirring for 30 min. The reaction mixture was stirred continuously for 12 h at room temperature and then poured into ice–water (200 ml). The solid obtained was filtered off, washed with water and dried at room temperature. Colorless crystals of the title compound suitable for X-ray structure analysis were obtained by evaporation of an ethanol solution over a period of one week.
H atoms were placed in calculated positions with C—H = 0.93 Å (aromatic) and 0.96 Å (methyl), and refined in riding mode with Uiso(H) = 1.2Ueq(C) (aromatic) and Uiso(H) = 1.5Ueq(C) (methyl).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C16H12O5S | Dx = 1.445 Mg m−3 |
Mr = 316.32 | Melting point: 493 K |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 1900 reflections |
a = 23.319 (3) Å | θ = 2.4–22.8° |
b = 9.0865 (12) Å | µ = 0.24 mm−1 |
c = 13.7280 (17) Å | T = 298 K |
V = 2908.8 (6) Å3 | Block, colourless |
Z = 8 | 0.48 × 0.35 × 0.23 mm |
F(000) = 1312 |
Siemens SMART CCD area-detector diffractometer | 2557 independent reflections |
Radiation source: fine-focus sealed tube | 1340 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.077 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −27→25 |
Tmin = 0.892, Tmax = 0.946 | k = −6→10 |
11238 measured reflections | l = −16→15 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0635P)2 + 1.4P] where P = (Fo2 + 2Fc2)/3 |
2557 reflections | (Δ/σ)max < 0.001 |
200 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C16H12O5S | V = 2908.8 (6) Å3 |
Mr = 316.32 | Z = 8 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 23.319 (3) Å | µ = 0.24 mm−1 |
b = 9.0865 (12) Å | T = 298 K |
c = 13.7280 (17) Å | 0.48 × 0.35 × 0.23 mm |
Siemens SMART CCD area-detector diffractometer | 2557 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1340 reflections with I > 2σ(I) |
Tmin = 0.892, Tmax = 0.946 | Rint = 0.077 |
11238 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.21 e Å−3 |
2557 reflections | Δρmin = −0.27 e Å−3 |
200 parameters |
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 | ||
O1 | 0.06623 (10) | 0.5712 (3) | 0.1179 (2) | 0.0475 (7) | |
O2 | 0.01987 (13) | 0.7814 (3) | 0.1253 (2) | 0.0753 (10) | |
O3 | 0.17597 (10) | 0.1409 (3) | 0.1092 (2) | 0.0554 (8) | |
O4 | 0.25437 (12) | 0.0001 (4) | 0.0562 (3) | 0.0813 (11) | |
O5 | 0.15694 (13) | −0.0921 (3) | 0.0244 (2) | 0.0686 (9) | |
S1 | 0.19688 (4) | 0.02586 (12) | 0.02911 (9) | 0.0554 (4) | |
C1 | 0.01573 (17) | 0.6497 (5) | 0.1241 (3) | 0.0511 (11) | |
C2 | −0.03663 (17) | 0.5658 (5) | 0.1266 (3) | 0.0518 (11) | |
H2 | −0.0712 | 0.6168 | 0.1297 | 0.062* | |
C3 | −0.03837 (15) | 0.4190 (4) | 0.1249 (3) | 0.0443 (10) | |
C4 | 0.01530 (14) | 0.3395 (4) | 0.1195 (3) | 0.0402 (9) | |
C5 | 0.06587 (16) | 0.4202 (4) | 0.1156 (3) | 0.0397 (9) | |
C6 | 0.11874 (15) | 0.3532 (4) | 0.1088 (3) | 0.0430 (10) | |
H6 | 0.1521 | 0.4088 | 0.1047 | 0.052* | |
C7 | 0.12071 (15) | 0.2032 (4) | 0.1081 (3) | 0.0431 (10) | |
C8 | 0.07195 (17) | 0.1177 (4) | 0.1123 (3) | 0.0529 (11) | |
H8 | 0.0743 | 0.0155 | 0.1116 | 0.063* | |
C9 | 0.01984 (17) | 0.1871 (4) | 0.1176 (3) | 0.0514 (11) | |
H9 | −0.0134 | 0.1306 | 0.1199 | 0.062* | |
C10 | −0.09430 (15) | 0.3386 (5) | 0.1251 (3) | 0.0669 (13) | |
H10A | −0.1251 | 0.4079 | 0.1317 | 0.100* | |
H10B | −0.0951 | 0.2708 | 0.1787 | 0.100* | |
H10C | −0.0985 | 0.2855 | 0.0651 | 0.100* | |
C11 | 0.19416 (16) | 0.1231 (4) | −0.0797 (3) | 0.0444 (10) | |
C12 | 0.24038 (18) | 0.2080 (5) | −0.1072 (4) | 0.0699 (14) | |
H12 | 0.2721 | 0.2163 | −0.0665 | 0.084* | |
C13 | 0.2393 (3) | 0.2794 (6) | −0.1940 (5) | 0.0937 (18) | |
H13 | 0.2705 | 0.3363 | −0.2131 | 0.112* | |
C14 | 0.1923 (3) | 0.2683 (6) | −0.2538 (4) | 0.0906 (18) | |
H14 | 0.1919 | 0.3175 | −0.3132 | 0.109* | |
C15 | 0.1467 (2) | 0.1859 (6) | −0.2267 (4) | 0.0723 (14) | |
H15 | 0.1149 | 0.1795 | −0.2675 | 0.087* | |
C16 | 0.14680 (18) | 0.1116 (5) | −0.1394 (3) | 0.0583 (12) | |
H16 | 0.1155 | 0.0547 | −0.1209 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0504 (16) | 0.0403 (16) | 0.0519 (19) | −0.0075 (12) | −0.0003 (14) | −0.0038 (13) |
O2 | 0.089 (2) | 0.0449 (19) | 0.093 (3) | 0.0008 (16) | −0.0127 (19) | −0.0033 (18) |
O3 | 0.0567 (16) | 0.0623 (18) | 0.0473 (19) | 0.0100 (14) | −0.0067 (14) | −0.0124 (15) |
O4 | 0.0632 (18) | 0.099 (3) | 0.082 (2) | 0.0411 (17) | −0.0239 (17) | −0.0130 (19) |
O5 | 0.084 (2) | 0.0457 (17) | 0.076 (2) | −0.0071 (15) | 0.0033 (18) | −0.0047 (16) |
S1 | 0.0583 (7) | 0.0514 (6) | 0.0566 (8) | 0.0129 (5) | −0.0072 (6) | −0.0057 (6) |
C1 | 0.063 (3) | 0.050 (3) | 0.041 (3) | −0.003 (2) | −0.005 (2) | −0.003 (2) |
C2 | 0.050 (2) | 0.067 (3) | 0.039 (3) | 0.007 (2) | −0.003 (2) | −0.007 (2) |
C3 | 0.045 (2) | 0.056 (3) | 0.032 (2) | −0.0075 (19) | 0.0005 (18) | −0.008 (2) |
C4 | 0.045 (2) | 0.045 (2) | 0.030 (2) | −0.0130 (18) | 0.0001 (18) | −0.0077 (18) |
C5 | 0.050 (2) | 0.037 (2) | 0.031 (2) | −0.0074 (18) | −0.0024 (19) | −0.0035 (17) |
C6 | 0.045 (2) | 0.045 (2) | 0.039 (2) | −0.0116 (18) | 0.0002 (18) | −0.0040 (19) |
C7 | 0.050 (2) | 0.045 (2) | 0.034 (2) | 0.0005 (19) | 0.0018 (19) | −0.0047 (19) |
C8 | 0.065 (3) | 0.037 (2) | 0.057 (3) | −0.007 (2) | 0.003 (2) | −0.003 (2) |
C9 | 0.053 (3) | 0.044 (2) | 0.057 (3) | −0.018 (2) | 0.003 (2) | −0.006 (2) |
C10 | 0.047 (2) | 0.083 (3) | 0.071 (4) | −0.016 (2) | 0.003 (2) | −0.011 (3) |
C11 | 0.043 (2) | 0.043 (2) | 0.047 (3) | 0.0069 (19) | −0.001 (2) | −0.009 (2) |
C12 | 0.061 (3) | 0.083 (3) | 0.066 (4) | −0.014 (3) | 0.003 (3) | −0.018 (3) |
C13 | 0.113 (5) | 0.099 (4) | 0.069 (4) | −0.029 (4) | 0.031 (4) | −0.004 (4) |
C14 | 0.146 (6) | 0.071 (4) | 0.055 (4) | 0.016 (4) | 0.016 (4) | 0.002 (3) |
C15 | 0.090 (4) | 0.073 (3) | 0.055 (4) | 0.022 (3) | −0.015 (3) | −0.007 (3) |
C16 | 0.054 (3) | 0.058 (3) | 0.063 (3) | 0.003 (2) | −0.004 (2) | −0.005 (2) |
O1—C5 | 1.373 (4) | C7—C8 | 1.378 (5) |
O1—C1 | 1.379 (4) | C8—C9 | 1.371 (5) |
O2—C1 | 1.201 (4) | C8—H8 | 0.9300 |
O3—C7 | 1.407 (4) | C9—H9 | 0.9300 |
O3—S1 | 1.594 (3) | C10—H10A | 0.9600 |
O4—S1 | 1.411 (3) | C10—H10B | 0.9600 |
O5—S1 | 1.421 (3) | C10—H10C | 0.9600 |
S1—C11 | 1.736 (4) | C11—C12 | 1.378 (5) |
C1—C2 | 1.440 (5) | C11—C16 | 1.379 (5) |
C2—C3 | 1.334 (5) | C12—C13 | 1.358 (7) |
C2—H2 | 0.9300 | C12—H12 | 0.9300 |
C3—C4 | 1.447 (5) | C13—C14 | 1.372 (7) |
C3—C10 | 1.495 (5) | C13—H13 | 0.9300 |
C4—C9 | 1.389 (5) | C14—C15 | 1.354 (7) |
C4—C5 | 1.390 (4) | C14—H14 | 0.9300 |
C5—C6 | 1.378 (5) | C15—C16 | 1.376 (6) |
C6—C7 | 1.364 (5) | C15—H15 | 0.9300 |
C6—H6 | 0.9300 | C16—H16 | 0.9300 |
C5—O1—C1 | 120.9 (3) | C9—C8—H8 | 120.8 |
C7—O3—S1 | 122.4 (2) | C7—C8—H8 | 120.8 |
O4—S1—O5 | 120.6 (2) | C8—C9—C4 | 121.8 (3) |
O4—S1—O3 | 102.59 (17) | C8—C9—H9 | 119.1 |
O5—S1—O3 | 109.02 (17) | C4—C9—H9 | 119.1 |
O4—S1—C11 | 110.2 (2) | C3—C10—H10A | 109.5 |
O5—S1—C11 | 108.70 (19) | C3—C10—H10B | 109.5 |
O3—S1—C11 | 104.37 (16) | H10A—C10—H10B | 109.5 |
O2—C1—O1 | 116.6 (4) | C3—C10—H10C | 109.5 |
O2—C1—C2 | 126.5 (4) | H10A—C10—H10C | 109.5 |
O1—C1—C2 | 116.9 (3) | H10B—C10—H10C | 109.5 |
C3—C2—C1 | 123.7 (4) | C12—C11—C16 | 120.4 (4) |
C3—C2—H2 | 118.2 | C12—C11—S1 | 119.5 (3) |
C1—C2—H2 | 118.2 | C16—C11—S1 | 120.1 (3) |
C2—C3—C4 | 118.3 (3) | C13—C12—C11 | 119.5 (5) |
C2—C3—C10 | 121.0 (4) | C13—C12—H12 | 120.2 |
C4—C3—C10 | 120.7 (4) | C11—C12—H12 | 120.2 |
C9—C4—C5 | 117.4 (3) | C12—C13—C14 | 120.4 (5) |
C9—C4—C3 | 124.4 (3) | C12—C13—H13 | 119.8 |
C5—C4—C3 | 118.2 (3) | C14—C13—H13 | 119.8 |
O1—C5—C6 | 115.9 (3) | C15—C14—C13 | 120.3 (5) |
O1—C5—C4 | 122.1 (3) | C15—C14—H14 | 119.9 |
C6—C5—C4 | 121.9 (3) | C13—C14—H14 | 119.9 |
C7—C6—C5 | 118.2 (3) | C14—C15—C16 | 120.5 (5) |
C7—C6—H6 | 120.9 | C14—C15—H15 | 119.7 |
C5—C6—H6 | 120.9 | C16—C15—H15 | 119.7 |
C6—C7—C8 | 122.4 (3) | C15—C16—C11 | 118.9 (4) |
C6—C7—O3 | 115.6 (3) | C15—C16—H16 | 120.6 |
C8—C7—O3 | 121.9 (3) | C11—C16—H16 | 120.6 |
C9—C8—C7 | 118.3 (4) | ||
C7—O3—S1—O4 | 177.3 (3) | C5—C6—C7—O3 | −174.9 (3) |
C7—O3—S1—O5 | −53.7 (3) | S1—O3—C7—C6 | −125.2 (3) |
C7—O3—S1—C11 | 62.3 (3) | S1—O3—C7—C8 | 58.8 (5) |
C5—O1—C1—O2 | −179.7 (4) | C6—C7—C8—C9 | −0.1 (6) |
C5—O1—C1—C2 | −0.8 (5) | O3—C7—C8—C9 | 175.6 (4) |
O2—C1—C2—C3 | 179.8 (4) | C7—C8—C9—C4 | −0.6 (6) |
O1—C1—C2—C3 | 1.1 (6) | C5—C4—C9—C8 | 0.2 (6) |
C1—C2—C3—C4 | −0.4 (6) | C3—C4—C9—C8 | 179.9 (4) |
C1—C2—C3—C10 | −178.4 (4) | O4—S1—C11—C12 | −23.7 (4) |
C2—C3—C4—C9 | 179.7 (4) | O5—S1—C11—C12 | −157.9 (3) |
C10—C3—C4—C9 | −2.2 (6) | O3—S1—C11—C12 | 85.8 (3) |
C2—C3—C4—C5 | −0.6 (5) | O4—S1—C11—C16 | 154.3 (3) |
C10—C3—C4—C5 | 177.5 (4) | O5—S1—C11—C16 | 20.0 (4) |
C1—O1—C5—C6 | 179.6 (3) | O3—S1—C11—C16 | −96.2 (3) |
C1—O1—C5—C4 | −0.1 (5) | C16—C11—C12—C13 | −0.6 (6) |
C9—C4—C5—O1 | −179.5 (3) | S1—C11—C12—C13 | 177.4 (4) |
C3—C4—C5—O1 | 0.8 (5) | C11—C12—C13—C14 | 0.5 (8) |
C9—C4—C5—C6 | 0.8 (6) | C12—C13—C14—C15 | 0.0 (8) |
C3—C4—C5—C6 | −178.9 (3) | C13—C14—C15—C16 | −0.4 (8) |
O1—C5—C6—C7 | 178.8 (3) | C14—C15—C16—C11 | 0.3 (7) |
C4—C5—C6—C7 | −1.5 (6) | C12—C11—C16—C15 | 0.2 (6) |
C5—C6—C7—C8 | 1.1 (6) | S1—C11—C16—C15 | −177.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O4i | 0.93 | 2.43 | 3.325 (4) | 163 |
C8—H8···O2ii | 0.93 | 2.48 | 3.293 (5) | 145 |
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C16H12O5S |
Mr | 316.32 |
Crystal system, space group | Orthorhombic, Pbcn |
Temperature (K) | 298 |
a, b, c (Å) | 23.319 (3), 9.0865 (12), 13.7280 (17) |
V (Å3) | 2908.8 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.48 × 0.35 × 0.23 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.892, 0.946 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11238, 2557, 1340 |
Rint | 0.077 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.164, 1.09 |
No. of reflections | 2557 |
No. of parameters | 200 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.27 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O4i | 0.93 | 2.43 | 3.325 (4) | 162.7 |
C8—H8···O2ii | 0.93 | 2.48 | 3.293 (5) | 145.4 |
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) x, y−1, z. |
Coumarin derivatives exhibit a wide variety of pharmacological activities including anti-HIV (Xie et al., 2001), antibacterial (Tanitame et al., 2004), antioxidant (Shao et al., 1997), antithrombotic (Rendenbach-Müller et al., 1994) and antiinflammatory (Pochet et al., 1996) activities. We have recently reported the crystal structures of some coumarin derivatives (Yang et al., 2007, 2006). As part of our study of the crystal structures of coumarin derivatives, we report here the crystal structure of the title coumarin derivative.
The molecular structure is shown in Fig. 1. The dihedral angle between the coumarin ring system and the phenyl ring is 65.9 (1)°. The terminal S═O bond distances of 1.411 (3) and 1.421 (3) Å agree with 1.4207 (19) and 1.4331 (19) Å found in a related compound, 4-methyl-7-phenylsulfonamido-2H-1-benzopyran-2-one (Yang et al., 2007).
In the crystal the molecules are linked by weak C—H···O hydrogen bonding to form the ribbon structure (Table 1 and Fig. 2).