8-Formyl-4-methyl-2-oxo-2H-chromen-7-yl 4-methyl-benzenesulfonate.

In the title compound, C(18)H(14)O(6)S, the coumarin ring system is nearly planar, with a maximum out-of-plane deviation of 0.032 (2) Å. The dihedral angle between the benzene ring and the coumarin ring system is 32.41 (8)°. The crystal packing is stabilized by inter-molecular C-H⋯O inter-actions, generating C(8), C(10) and C(11) chains and an R(2) (2)(10) ring. The formyl group is disordered over two sets of sites, with occupancies of 0.548 (5) and 0.452 (5).

Related literature

For the biological activity of coumarins, see: Carlton et al. (1996 ▶); El-Agrody et al. (2001 ▶); Emmanuel-Giota et al. (2001 ▶); Kulkarni et al. (2006 ▶); Kalkhambkar et al. (2008 ▶); Shaker (1996 ▶); Yang et al. (2005 ▶); Zhou et al. (2000 ▶). For a related structure, see: Yuvaraj et al. (2011 ▶).

Experimental

Crystal data

C18H14O6S

M = 358.35

Orthorhombic,

a = 17.6174 (7) Å

b = 7.2025 (3) Å

c = 25.7706 (10) Å

V = 3270.0 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.14 × 0.13 × 0.13 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

48911 measured reflections

4234 independent reflections

3095 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.135

S = 1.02

4234 reflections

238 parameters

14 restraints

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.37 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018927/is2704sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018927/is2704Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018927/is2704Isup3.cml

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

C18H14O6S	F(000) = 1488
Mr = 358.35	Dx = 1.456 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6552 reflections
a = 17.6174 (7) Å	θ = 2.3–26.6°
b = 7.2025 (3) Å	µ = 0.23 mm−1
c = 25.7706 (10) Å	T = 293 K
V = 3270.0 (2) Å3	Plate, colorless
Z = 8	0.14 × 0.13 × 0.13 mm

Bruker SMART APEX CCD area-detector diffractometer	3095 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
graphite	θmax = 28.7°, θmin = 1.6°
φ and ω scans	h = −23→23
48911 measured reflections	k = −9→9
4234 independent reflections	l = −34→34

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0672P)2 + 0.8242P] where P = (Fo2 + 2Fc2)/3
4234 reflections	(Δ/σ)max = 0.001
238 parameters	Δρmax = 0.26 e Å−3
14 restraints	Δρmin = −0.37 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	Occ. (<1)
C1	0.70245 (18)	0.5004 (5)	0.48070 (11)	0.1076 (9)
H1A	0.7160	0.4100	0.4550	0.161*
H1B	0.7446	0.5202	0.5037	0.161*
H1C	0.6895	0.6152	0.4639	0.161*
C2	0.63513 (13)	0.4313 (3)	0.51137 (8)	0.0712 (5)
C3	0.62555 (11)	0.4882 (3)	0.56260 (8)	0.0652 (5)
H3	0.6605	0.5692	0.5773	0.078*
C4	0.56508 (10)	0.4264 (3)	0.59184 (7)	0.0585 (4)
H4	0.5587	0.4663	0.6259	0.070*
C5	0.51398 (10)	0.3038 (2)	0.56962 (7)	0.0563 (4)
C6	0.52174 (14)	0.2479 (3)	0.51834 (8)	0.0708 (5)
H6	0.4866	0.1677	0.5034	0.085*
C7	0.58218 (16)	0.3130 (3)	0.49004 (8)	0.0791 (6)
H7	0.5875	0.2763	0.4556	0.095*
C8	0.54138 (10)	0.0811 (3)	0.67455 (7)	0.0578 (4)
C9	0.61696 (10)	0.0624 (2)	0.65996 (6)	0.0525 (4)
C10	0.67090 (9)	0.1065 (2)	0.69784 (6)	0.0472 (3)
C11	0.65136 (9)	0.1600 (2)	0.74813 (6)	0.0495 (4)
C12	0.57417 (11)	0.1691 (3)	0.76024 (7)	0.0631 (5)
H12	0.5595	0.2012	0.7937	0.076*
C13	0.51960 (10)	0.1319 (3)	0.72389 (8)	0.0680 (5)
H13	0.4684	0.1408	0.7324	0.082*
C14	0.63965 (14)	−0.0075 (4)	0.60842 (8)	0.0772 (6)
H14A	0.6916	0.0009	0.6025	0.093*	0.548 (5)
H14B	0.5992	−0.0394	0.5871	0.093*	0.452 (5)
C15	0.80427 (9)	0.1381 (2)	0.71607 (7)	0.0534 (4)
C16	0.78344 (10)	0.1945 (2)	0.76774 (7)	0.0550 (4)
H16	0.8220	0.2264	0.7907	0.066*
C17	0.71185 (10)	0.2035 (2)	0.78441 (6)	0.0513 (4)
C18	0.69355 (13)	0.2552 (3)	0.83935 (7)	0.0720 (5)
H18A	0.7398	0.2772	0.8581	0.108*
H18B	0.6660	0.1558	0.8555	0.108*
H18C	0.6631	0.3658	0.8396	0.108*
O1	0.38782 (9)	0.1146 (3)	0.57769 (7)	0.0957 (6)
O2	0.41980 (9)	0.3388 (2)	0.64607 (6)	0.0814 (4)
O3	0.48511 (7)	0.03917 (19)	0.63759 (6)	0.0685 (4)
O4A	0.60724 (19)	−0.0694 (4)	0.57442 (11)	0.0912 (13)	0.548 (5)
O4B	0.6962 (2)	−0.0293 (10)	0.59052 (17)	0.136 (2)	0.452 (5)
O5	0.74534 (6)	0.09179 (18)	0.68306 (4)	0.0539 (3)
O6	0.86731 (7)	0.1254 (2)	0.69874 (6)	0.0738 (4)
S1	0.44287 (3)	0.20842 (8)	0.60799 (2)	0.06651 (18)

	U11	U22	U33	U12	U13	U23
C1	0.113 (2)	0.114 (2)	0.0953 (18)	0.0111 (18)	0.0263 (16)	0.0339 (16)
C2	0.0815 (14)	0.0662 (12)	0.0660 (11)	0.0140 (10)	0.0039 (10)	0.0138 (10)
C3	0.0622 (11)	0.0601 (10)	0.0735 (12)	0.0003 (9)	−0.0090 (9)	0.0002 (9)
C4	0.0580 (10)	0.0607 (10)	0.0569 (9)	0.0028 (8)	−0.0095 (8)	−0.0079 (8)
C5	0.0581 (9)	0.0538 (9)	0.0570 (9)	0.0043 (8)	−0.0142 (8)	−0.0006 (7)
C6	0.0929 (15)	0.0587 (10)	0.0607 (10)	0.0035 (10)	−0.0224 (10)	−0.0065 (9)
C7	0.1139 (18)	0.0721 (13)	0.0513 (10)	0.0132 (13)	−0.0026 (11)	−0.0005 (9)
C8	0.0468 (8)	0.0596 (10)	0.0671 (10)	−0.0013 (7)	−0.0085 (7)	0.0120 (8)
C9	0.0506 (9)	0.0523 (9)	0.0546 (9)	0.0037 (7)	−0.0045 (7)	0.0034 (7)
C10	0.0425 (8)	0.0477 (8)	0.0513 (8)	0.0046 (6)	−0.0005 (6)	0.0047 (6)
C11	0.0489 (8)	0.0501 (8)	0.0496 (8)	0.0055 (7)	0.0010 (7)	0.0078 (7)
C12	0.0554 (10)	0.0788 (12)	0.0549 (9)	0.0106 (9)	0.0095 (8)	0.0116 (9)
C13	0.0442 (9)	0.0882 (14)	0.0715 (11)	0.0044 (9)	0.0055 (8)	0.0176 (10)
C14	0.0680 (13)	0.0969 (16)	0.0667 (12)	0.0167 (12)	−0.0161 (11)	−0.0185 (11)
C15	0.0473 (8)	0.0543 (9)	0.0588 (9)	0.0035 (7)	−0.0040 (7)	0.0000 (7)
C16	0.0550 (9)	0.0540 (9)	0.0559 (9)	0.0008 (7)	−0.0089 (7)	−0.0021 (7)
C17	0.0589 (9)	0.0468 (8)	0.0483 (8)	0.0035 (7)	−0.0022 (7)	0.0030 (7)
C18	0.0799 (13)	0.0841 (13)	0.0519 (9)	0.0003 (11)	0.0025 (9)	−0.0045 (9)
O1	0.0631 (9)	0.1010 (12)	0.1230 (14)	−0.0170 (8)	−0.0409 (9)	0.0130 (10)
O2	0.0605 (8)	0.0953 (11)	0.0884 (10)	0.0165 (8)	0.0070 (7)	0.0052 (9)
O3	0.0530 (7)	0.0674 (8)	0.0850 (9)	−0.0080 (6)	−0.0181 (6)	0.0112 (7)
O4A	0.111 (3)	0.084 (2)	0.0780 (19)	0.0174 (17)	−0.0341 (17)	−0.0248 (15)
O4B	0.078 (3)	0.241 (6)	0.089 (3)	−0.013 (3)	0.016 (2)	−0.065 (3)
O5	0.0435 (6)	0.0660 (7)	0.0522 (6)	0.0061 (5)	−0.0009 (5)	−0.0045 (5)
O6	0.0454 (7)	0.0988 (11)	0.0773 (9)	0.0045 (7)	0.0020 (6)	−0.0126 (8)
S1	0.0460 (2)	0.0741 (3)	0.0795 (3)	−0.0003 (2)	−0.0156 (2)	0.0070 (2)

C1—C2	1.510 (3)	C11—C12	1.397 (2)
C1—H1A	0.9600	C11—C17	1.452 (2)
C1—H1B	0.9600	C12—C13	1.369 (3)
C1—H1C	0.9600	C12—H12	0.9300
C2—C7	1.378 (3)	C13—H13	0.9300
C2—C3	1.393 (3)	C14—O4B	1.109 (4)
C3—C4	1.379 (3)	C14—O4A	1.137 (3)
C3—H3	0.9300	C14—H14A	0.9300
C4—C5	1.385 (2)	C14—H14B	0.9300
C4—H4	0.9300	C15—O6	1.200 (2)
C5—C6	1.388 (3)	C15—O5	1.383 (2)
C5—S1	1.737 (2)	C15—C16	1.440 (2)
C6—C7	1.373 (3)	C16—C17	1.334 (2)
C6—H6	0.9300	C16—H16	0.9300
C7—H7	0.9300	C17—C18	1.499 (2)
C8—C13	1.378 (3)	C18—H18A	0.9600
C8—C9	1.390 (2)	C18—H18B	0.9600
C8—O3	1.407 (2)	C18—H18C	0.9600
C9—C10	1.399 (2)	O1—S1	1.4165 (16)
C9—C14	1.476 (3)	O2—S1	1.4179 (17)
C10—O5	1.3696 (19)	O3—S1	1.6191 (14)
C10—C11	1.395 (2)
C2—C1—H1A	109.5	C12—C11—C17	124.09 (16)
C2—C1—H1B	109.5	C13—C12—C11	121.44 (17)
H1A—C1—H1B	109.5	C13—C12—H12	119.3
C2—C1—H1C	109.5	C11—C12—H12	119.3
H1A—C1—H1C	109.5	C12—C13—C8	119.21 (17)
H1B—C1—H1C	109.5	C12—C13—H13	120.4
C7—C2—C3	118.6 (2)	C8—C13—H13	120.4
C7—C2—C1	121.8 (2)	O4B—C14—C9	131.8 (3)
C3—C2—C1	119.6 (2)	O4A—C14—C9	133.7 (3)
C4—C3—C2	121.12 (19)	C9—C14—H14A	113.1
C4—C3—H3	119.4	C9—C14—H14B	114.2
C2—C3—H3	119.4	O6—C15—O5	116.59 (16)
C3—C4—C5	118.82 (17)	O6—C15—C16	126.95 (16)
C3—C4—H4	120.6	O5—C15—C16	116.45 (15)
C5—C4—H4	120.6	C17—C16—C15	123.55 (16)
C4—C5—C6	120.96 (19)	C17—C16—H16	118.2
C4—C5—S1	119.03 (14)	C15—C16—H16	118.2
C6—C5—S1	119.89 (16)	C16—C17—C11	118.42 (15)
C7—C6—C5	118.9 (2)	C16—C17—C18	121.31 (17)
C7—C6—H6	120.6	C11—C17—C18	120.27 (16)
C5—C6—H6	120.6	C17—C18—H18A	109.5
C6—C7—C2	121.63 (19)	C17—C18—H18B	109.5
C6—C7—H7	119.2	H18A—C18—H18B	109.5
C2—C7—H7	119.2	C17—C18—H18C	109.5
C13—C8—C9	122.83 (17)	H18A—C18—H18C	109.5
C13—C8—O3	119.04 (16)	H18B—C18—H18C	109.5
C9—C8—O3	118.08 (17)	C8—O3—S1	118.74 (12)
C8—C9—C10	116.10 (16)	C10—O5—C15	121.95 (13)
C8—C9—C14	122.41 (17)	O1—S1—O2	120.07 (11)
C10—C9—C14	121.43 (16)	O1—S1—O3	102.44 (9)
O5—C10—C11	121.05 (14)	O2—S1—O3	107.72 (9)
O5—C10—C9	116.03 (14)	O1—S1—C5	111.62 (10)
C11—C10—C9	122.91 (15)	O2—S1—C5	109.80 (10)
C10—C11—C12	117.44 (16)	O3—S1—C5	103.55 (8)
C10—C11—C17	118.47 (15)
C7—C2—C3—C4	0.8 (3)	C8—C9—C14—O4B	179.2 (6)
C1—C2—C3—C4	−179.4 (2)	C10—C9—C14—O4B	−3.5 (7)
C2—C3—C4—C5	0.9 (3)	C8—C9—C14—O4A	−7.1 (5)
C3—C4—C5—C6	−2.0 (3)	C10—C9—C14—O4A	170.2 (3)
C3—C4—C5—S1	173.98 (14)	O6—C15—C16—C17	−179.34 (19)
C4—C5—C6—C7	1.5 (3)	O5—C15—C16—C17	0.0 (3)
S1—C5—C6—C7	−174.49 (16)	C15—C16—C17—C11	−2.1 (3)
C5—C6—C7—C2	0.3 (3)	C15—C16—C17—C18	177.28 (18)
C3—C2—C7—C6	−1.4 (3)	C10—C11—C17—C16	1.5 (2)
C1—C2—C7—C6	178.9 (2)	C12—C11—C17—C16	−178.16 (18)
C13—C8—C9—C10	−2.8 (3)	C10—C11—C17—C18	−177.90 (17)
O3—C8—C9—C10	179.68 (15)	C12—C11—C17—C18	2.5 (3)
C13—C8—C9—C14	174.6 (2)	C13—C8—O3—S1	80.5 (2)
O3—C8—C9—C14	−2.9 (3)	C9—C8—O3—S1	−101.90 (18)
C8—C9—C10—O5	−178.68 (15)	C11—C10—O5—C15	−3.4 (2)
C14—C9—C10—O5	3.9 (3)	C9—C10—O5—C15	177.47 (15)
C8—C9—C10—C11	2.2 (2)	O6—C15—O5—C10	−177.79 (16)
C14—C9—C10—C11	−175.20 (18)	C16—C15—O5—C10	2.8 (2)
O5—C10—C11—C12	−179.13 (16)	C8—O3—S1—O1	−175.87 (15)
C9—C10—C11—C12	−0.1 (3)	C8—O3—S1—O2	−48.35 (16)
O5—C10—C11—C17	1.2 (2)	C8—O3—S1—C5	67.94 (15)
C9—C10—C11—C17	−179.74 (15)	C4—C5—S1—O1	169.10 (15)
C10—C11—C12—C13	−1.7 (3)	C6—C5—S1—O1	−14.87 (19)
C17—C11—C12—C13	177.95 (18)	C4—C5—S1—O2	33.42 (17)
C11—C12—C13—C8	1.2 (3)	C6—C5—S1—O2	−150.56 (16)
C9—C8—C13—C12	1.2 (3)	C4—C5—S1—O3	−81.39 (16)
O3—C8—C13—C12	178.67 (18)	C6—C5—S1—O3	94.64 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O6i	0.93	2.56	3.326 (2)	140
C13—H13···O6ii	0.93	2.52	3.343 (2)	148
C16—H16···O2iii	0.93	2.51	3.433 (2)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O6i	0.93	2.56	3.326 (2)	140
C13—H13⋯O6ii	0.93	2.52	3.343 (2)	148
C16—H16⋯O2iii	0.93	2.51	3.433 (2)	175

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