4-Methyl-2-oxo-2H-chromen-7-yl 4-methyl-benzene-sulfonate.

In the title compound, C(17)H(14)O(5)S, the coumarin ring system is nearly planar, with a maximum deviation of 0.034 (2) Å from the mean plane. The dihedral angle between the benzene ring and the coumarin ring system is 56.11 (6)°. The crystal packing is stabilized by C-H⋯O hydrogen bonding, which forms a three-dimensional framework.

Related literature

For the biological activity of coumarin derivatives, see: Xie et al. (2001 ▶); Tanitame et al. (2004 ▶); Shao et al. (1997 ▶); Rendenbach-Müller et al. (1994 ▶); Pochet et al. (1996 ▶). For a related structure, see: Yang et al. (2007 ▶).

Experimental

Crystal data

C17H14O5S

M = 330.34

Triclinic,

a = 7.5582 (19) Å

b = 8.024 (2) Å

c = 13.336 (4) Å

α = 88.648 (8)°

β = 87.420 (7)°

γ = 74.341 (4)°

V = 777.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 153 K

0.54 × 0.41 × 0.40 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.885, T max = 0.913

8968 measured reflections

4451 independent reflections

3289 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.099

S = 1.00

4451 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.47 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812012238/fy2046sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012238/fy2046Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012238/fy2046Isup3.cml

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

C17H14O5S	Z = 2
Mr = 330.34	F(000) = 344
Triclinic, P1	Dx = 1.410 Mg m−3
a = 7.5582 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.024 (2) Å	Cell parameters from 2667 reflections
c = 13.336 (4) Å	θ = 2.6–30.0°
α = 88.648 (8)°	µ = 0.23 mm−1
β = 87.420 (7)°	T = 153 K
γ = 74.341 (4)°	Chip, colorless
V = 777.9 (3) Å3	0.54 × 0.41 × 0.40 mm

Rigaku AFC10/Saturn724+ diffractometer	4451 independent reflections
Radiation source: Rotating Anode	3289 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 28.5714 pixels mm-1	θmax = 30.0°, θmin = 2.8°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→10
Tmin = 0.885, Tmax = 0.913	l = −18→17
8968 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0315P)2 + 0.119P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
4451 reflections	Δρmax = 0.30 e Å−3
211 parameters	Δρmin = −0.47 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0116 (17)

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
S1	−0.05701 (5)	0.90186 (5)	0.20148 (3)	0.02605 (11)
O1	0.63814 (14)	0.58774 (12)	0.35269 (7)	0.0263 (2)
O2	0.11089 (15)	0.98205 (12)	0.22320 (7)	0.0270 (2)
O3	0.88672 (15)	0.39807 (14)	0.40502 (9)	0.0362 (3)
O4	−0.14270 (15)	0.87024 (14)	0.29442 (7)	0.0324 (3)
O5	−0.15830 (17)	1.02006 (14)	0.13018 (8)	0.0384 (3)
C1	0.7537 (2)	0.51511 (19)	0.42877 (12)	0.0276 (3)
C2	0.7040 (2)	0.58301 (19)	0.52862 (12)	0.0276 (3)
H2	0.7814	0.5339	0.5819	0.033*
C3	0.5524 (2)	0.71307 (18)	0.54922 (11)	0.0240 (3)
C4	0.43676 (19)	0.79009 (17)	0.46707 (10)	0.0211 (3)
C5	0.2782 (2)	0.92868 (17)	0.47851 (11)	0.0227 (3)
H5	0.2448	0.9795	0.5426	0.027*
C6	0.1701 (2)	0.99233 (17)	0.39833 (10)	0.0237 (3)
H6	0.0638	1.0872	0.4064	0.028*
C7	0.2198 (2)	0.91503 (17)	0.30561 (10)	0.0222 (3)
C8	0.3765 (2)	0.78118 (18)	0.28978 (10)	0.0242 (3)
H8	0.4094	0.7319	0.2253	0.029*
C9	0.48388 (19)	0.72125 (17)	0.37112 (11)	0.0218 (3)
C10	0.0542 (2)	0.70422 (18)	0.14554 (10)	0.0237 (3)
C11	0.0484 (2)	0.55129 (19)	0.19411 (12)	0.0301 (3)
H11	−0.0192	0.5528	0.2560	0.036*
C12	0.1434 (2)	0.3959 (2)	0.15060 (13)	0.0363 (4)
H12	0.1384	0.2902	0.1828	0.044*
C13	0.2454 (2)	0.3912 (2)	0.06117 (13)	0.0367 (4)
C14	0.2448 (2)	0.5469 (2)	0.01312 (12)	0.0373 (4)
H14	0.3111	0.5456	−0.0492	0.045*
C15	0.1497 (2)	0.7033 (2)	0.05420 (11)	0.0310 (3)
H15	0.1497	0.8089	0.0204	0.037*
C16	0.4986 (2)	0.7756 (2)	0.65416 (11)	0.0307 (3)
H16A	0.5894	0.7093	0.7004	0.037*
H16B	0.3773	0.7599	0.6731	0.037*
H16C	0.4938	0.8987	0.6575	0.037*
C17	0.3556 (3)	0.2207 (2)	0.01848 (17)	0.0579 (6)
H17A	0.4712	0.1806	0.0533	0.069*
H17B	0.3824	0.2354	−0.0533	0.069*
H17C	0.2849	0.1351	0.0276	0.069*

	U11	U22	U33	U12	U13	U23
S1	0.0268 (2)	0.02155 (18)	0.0275 (2)	−0.00202 (14)	−0.00334 (15)	−0.00134 (14)
O1	0.0219 (5)	0.0191 (5)	0.0340 (6)	0.0000 (4)	0.0056 (4)	−0.0021 (4)
O2	0.0322 (6)	0.0196 (5)	0.0294 (5)	−0.0069 (4)	−0.0047 (4)	0.0032 (4)
O3	0.0241 (6)	0.0242 (5)	0.0549 (7)	0.0013 (5)	0.0050 (5)	0.0014 (5)
O4	0.0301 (6)	0.0361 (6)	0.0309 (6)	−0.0090 (5)	0.0059 (5)	−0.0072 (5)
O5	0.0431 (7)	0.0268 (6)	0.0391 (6)	0.0033 (5)	−0.0153 (5)	0.0017 (5)
C1	0.0197 (7)	0.0198 (7)	0.0428 (9)	−0.0054 (6)	0.0024 (6)	0.0019 (6)
C2	0.0213 (7)	0.0235 (7)	0.0384 (8)	−0.0064 (6)	−0.0035 (6)	0.0024 (6)
C3	0.0211 (7)	0.0207 (7)	0.0320 (8)	−0.0086 (6)	−0.0010 (6)	−0.0003 (6)
C4	0.0191 (7)	0.0160 (6)	0.0287 (7)	−0.0058 (5)	0.0022 (6)	−0.0026 (5)
C5	0.0215 (7)	0.0186 (6)	0.0278 (7)	−0.0053 (5)	0.0036 (6)	−0.0053 (5)
C6	0.0212 (7)	0.0170 (6)	0.0320 (8)	−0.0036 (5)	0.0025 (6)	−0.0042 (6)
C7	0.0248 (7)	0.0168 (6)	0.0259 (7)	−0.0070 (6)	−0.0007 (6)	0.0010 (5)
C8	0.0272 (8)	0.0197 (7)	0.0252 (7)	−0.0062 (6)	0.0044 (6)	−0.0035 (5)
C9	0.0181 (7)	0.0150 (6)	0.0312 (7)	−0.0035 (5)	0.0055 (6)	−0.0022 (5)
C10	0.0254 (7)	0.0210 (7)	0.0240 (7)	−0.0046 (6)	−0.0025 (6)	−0.0014 (5)
C11	0.0331 (9)	0.0256 (8)	0.0317 (8)	−0.0080 (7)	−0.0019 (7)	0.0017 (6)
C12	0.0378 (10)	0.0211 (7)	0.0501 (10)	−0.0073 (7)	−0.0097 (8)	0.0008 (7)
C13	0.0276 (8)	0.0295 (8)	0.0517 (10)	−0.0031 (7)	−0.0080 (8)	−0.0139 (7)
C14	0.0322 (9)	0.0449 (10)	0.0327 (9)	−0.0066 (8)	0.0051 (7)	−0.0129 (7)
C15	0.0352 (9)	0.0282 (8)	0.0282 (8)	−0.0066 (7)	0.0009 (7)	0.0013 (6)
C16	0.0311 (9)	0.0295 (8)	0.0319 (8)	−0.0084 (7)	−0.0042 (7)	−0.0027 (6)
C17	0.0407 (11)	0.0384 (10)	0.0896 (16)	0.0010 (9)	−0.0060 (11)	−0.0315 (10)

S1—O5	1.4215 (11)	C8—C9	1.3824 (19)
S1—O4	1.4219 (11)	C8—H8	0.9500
S1—O2	1.6097 (11)	C10—C11	1.384 (2)
S1—C10	1.7485 (15)	C10—C15	1.387 (2)
O1—C9	1.3710 (16)	C11—C12	1.386 (2)
O1—C1	1.3817 (18)	C11—H11	0.9500
O2—C7	1.4104 (16)	C12—C13	1.386 (2)
O3—C1	1.2119 (18)	C12—H12	0.9500
C1—C2	1.446 (2)	C13—C14	1.389 (2)
C2—C3	1.348 (2)	C13—C17	1.507 (2)
C2—H2	0.9500	C14—C15	1.379 (2)
C3—C4	1.4521 (19)	C14—H14	0.9500
C3—C16	1.499 (2)	C15—H15	0.9500
C4—C9	1.3983 (19)	C16—H16A	0.9800
C4—C5	1.4028 (19)	C16—H16B	0.9800
C5—C6	1.3782 (19)	C16—H16C	0.9800
C5—H5	0.9500	C17—H17A	0.9800
C6—C7	1.3868 (19)	C17—H17B	0.9800
C6—H6	0.9500	C17—H17C	0.9800
C7—C8	1.379 (2)
O5—S1—O4	120.25 (8)	O1—C9—C4	121.76 (13)
O5—S1—O2	103.06 (6)	C8—C9—C4	122.18 (13)
O4—S1—O2	109.02 (6)	C11—C10—C15	121.11 (14)
O5—S1—C10	110.90 (7)	C11—C10—S1	119.45 (12)
O4—S1—C10	109.26 (7)	C15—C10—S1	119.43 (11)
O2—S1—C10	102.75 (6)	C10—C11—C12	118.67 (15)
C9—O1—C1	121.11 (12)	C10—C11—H11	120.7
C7—O2—S1	117.90 (8)	C12—C11—H11	120.7
O3—C1—O1	116.22 (14)	C11—C12—C13	121.42 (15)
O3—C1—C2	126.26 (15)	C11—C12—H12	119.3
O1—C1—C2	117.51 (13)	C13—C12—H12	119.3
C3—C2—C1	122.73 (14)	C12—C13—C14	118.46 (15)
C3—C2—H2	118.6	C12—C13—C17	120.29 (17)
C1—C2—H2	118.6	C14—C13—C17	121.25 (17)
C2—C3—C4	118.39 (13)	C15—C14—C13	121.24 (16)
C2—C3—C16	121.80 (14)	C15—C14—H14	119.4
C4—C3—C16	119.79 (13)	C13—C14—H14	119.4
C9—C4—C5	117.80 (13)	C14—C15—C10	119.03 (15)
C9—C4—C3	118.45 (13)	C14—C15—H15	120.5
C5—C4—C3	123.74 (13)	C10—C15—H15	120.5
C6—C5—C4	121.12 (13)	C3—C16—H16A	109.5
C6—C5—H5	119.4	C3—C16—H16B	109.5
C4—C5—H5	119.4	H16A—C16—H16B	109.5
C5—C6—C7	118.61 (13)	C3—C16—H16C	109.5
C5—C6—H6	120.7	H16A—C16—H16C	109.5
C7—C6—H6	120.7	H16B—C16—H16C	109.5
C8—C7—C6	122.58 (13)	C13—C17—H17A	109.5
C8—C7—O2	118.74 (12)	C13—C17—H17B	109.5
C6—C7—O2	118.60 (13)	H17A—C17—H17B	109.5
C7—C8—C9	117.65 (13)	C13—C17—H17C	109.5
C7—C8—H8	121.2	H17A—C17—H17C	109.5
C9—C8—H8	121.2	H17B—C17—H17C	109.5
O1—C9—C8	116.05 (12)
O5—S1—O2—C7	167.92 (10)	C1—O1—C9—C4	0.17 (19)
O4—S1—O2—C7	39.08 (11)	C7—C8—C9—O1	179.78 (12)
C10—S1—O2—C7	−76.75 (11)	C7—C8—C9—C4	1.0 (2)
C9—O1—C1—O3	−179.83 (12)	C5—C4—C9—O1	178.86 (12)
C9—O1—C1—C2	1.12 (19)	C3—C4—C9—O1	−2.0 (2)
O3—C1—C2—C3	−179.45 (15)	C5—C4—C9—C8	−2.4 (2)
O1—C1—C2—C3	−0.5 (2)	C3—C4—C9—C8	176.75 (12)
C1—C2—C3—C4	−1.3 (2)	O5—S1—C10—C11	−135.28 (13)
C1—C2—C3—C16	176.97 (13)	O4—S1—C10—C11	−0.47 (14)
C2—C3—C4—C9	2.54 (19)	O2—S1—C10—C11	115.18 (12)
C16—C3—C4—C9	−175.78 (13)	O5—S1—C10—C15	45.99 (14)
C2—C3—C4—C5	−178.39 (13)	O4—S1—C10—C15	−179.20 (12)
C16—C3—C4—C5	3.3 (2)	O2—S1—C10—C15	−63.55 (13)
C9—C4—C5—C6	1.5 (2)	C15—C10—C11—C12	1.2 (2)
C3—C4—C5—C6	−177.61 (13)	S1—C10—C11—C12	−177.49 (12)
C4—C5—C6—C7	0.8 (2)	C10—C11—C12—C13	1.1 (2)
C5—C6—C7—C8	−2.3 (2)	C11—C12—C13—C14	−2.6 (2)
C5—C6—C7—O2	−178.95 (12)	C11—C12—C13—C17	176.63 (15)
S1—O2—C7—C8	92.71 (14)	C12—C13—C14—C15	1.8 (2)
S1—O2—C7—C6	−90.55 (13)	C17—C13—C14—C15	−177.42 (16)
C6—C7—C8—C9	1.5 (2)	C13—C14—C15—C10	0.4 (2)
O2—C7—C8—C9	178.07 (12)	C11—C10—C15—C14	−2.0 (2)
C1—O1—C9—C8	−178.66 (12)	S1—C10—C15—C14	176.72 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4i	0.95	2.50	3.447 (2)	176
C6—H6···O3ii	0.95	2.49	3.380 (2)	156
C11—H11···O3iii	0.95	2.50	3.355 (2)	150
C12—H12···O2iv	0.95	2.58	3.506 (2)	165
C15—H15···O5v	0.95	2.41	3.284 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4i	0.95	2.50	3.447 (2)	176
C6—H6⋯O3ii	0.95	2.49	3.380 (2)	156
C11—H11⋯O3iii	0.95	2.50	3.355 (2)	150
C12—H12⋯O2iv	0.95	2.58	3.506 (2)	165
C15—H15⋯O5v	0.95	2.41	3.284 (2)	152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .