4-Methyl-2-oxo-2,3-dihydro-1-benzopyran-7-yl benzene-sulfonate.

The title compound, C(16)H(12)O(5)S, is a derivative of coumarin. The dihedral angle between the coumarin ring system and the phenyl ring is 65.9 (1)°. In the crystal structure, mol-ecules are linked by weak C-H⋯O hydrogen bonding to form molecular ribbons.

Related literature

For general background, see: Xie et al. (2001 ▶); Tanitame et al. (2004 ▶); Shao et al. (1997 ▶); Rendenbach-Müller et al. (1994 ▶); Pochet et al. (1996 ▶); Yang et al. (2007 ▶, 2006 ▶). For a related structure, see: Yang et al. (2007 ▶).

Experimental

Crystal data

C16H12O5S

M = 316.32

Orthorhombic,

a = 23.319 (3) Å

b = 9.0865 (12) Å

c = 13.7280 (17) Å

V = 2908.8 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 298 (2) K

0.48 × 0.35 × 0.23 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.892, T max = 0.946

11238 measured reflections

2557 independent reflections

1340 reflections with I > 2σ(I)

R int = 0.077

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.164

S = 1.09

2557 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032005/xu2456sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032005/xu2456Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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	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

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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) .