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

In the title compound, C(17)H(14)O(6)S, the 2H-chromene ring is essentially planar, with a maximum deviation of 0.016 (1) Å. The dihedral angle between the 2H-chromene and the benzene rings is 54.61 (5)°. The C atom of the meth-oxy group is close to coplanar with its attached ring [deviation = 0.082 (2) Å]. In the crystal, mol-ecules are connected via C-H⋯O hydrogen bonds, forming sheets lying parallel to the bc plane. Weak C-H⋯π inter-actions are also observed.

Related literature

For applications and properties of coumarin derivatives, see: Sinha et al. (2011 ▶); Valente et al. (2010) ▶; Radanyi et al. (2008 ▶); Han et al. (2005 ▶); Cheng et al. (2004 ▶). For further synthetic details, see: Fusegi et al. (2009 ▶).

Experimental

Crystal data

C17H14O6S

M = 346.34

Triclinic,

a = 7.9801 (3) Å

b = 9.2234 (4) Å

c = 10.9682 (5) Å

α = 99.049 (1)°

β = 90.288 (1)°

γ = 93.945 (1)°

V = 795.26 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.39 × 0.34 × 0.17 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.913, T max = 0.962

21468 measured reflections

5907 independent reflections

4468 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.131

S = 1.04

5907 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811049476/hb6524sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049476/hb6524Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811049476/hb6524Isup3.cml

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

C17H14O6S	Z = 2
Mr = 346.34	F(000) = 360
Triclinic, P1	Dx = 1.446 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9801 (3) Å	Cell parameters from 7512 reflections
b = 9.2234 (4) Å	θ = 2.6–32.8°
c = 10.9682 (5) Å	µ = 0.23 mm−1
α = 99.049 (1)°	T = 296 K
β = 90.288 (1)°	Block, colourless
γ = 93.945 (1)°	0.39 × 0.34 × 0.17 mm
V = 795.26 (6) Å3

Bruker APEXII DUO CCD diffractometer	5907 independent reflections
Radiation source: fine-focus sealed tube	4468 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 33.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.913, Tmax = 0.962	k = −14→12
21468 measured reflections	l = −16→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0651P)2 + 0.114P] where P = (Fo2 + 2Fc2)/3
5907 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.33642 (4)	0.69504 (3)	0.53507 (3)	0.04487 (10)
O1	0.44708 (11)	0.69936 (10)	0.65864 (8)	0.04511 (19)
O2	0.33520 (13)	0.28756 (9)	0.86131 (8)	0.0501 (2)
O3	0.45083 (14)	0.76349 (12)	0.45924 (10)	0.0622 (3)
O4	0.26867 (14)	0.54843 (11)	0.49601 (9)	0.0583 (3)
O5	0.2954 (2)	0.08977 (12)	0.94880 (12)	0.0839 (4)
O6	−0.18253 (12)	1.08511 (11)	0.72509 (10)	0.0568 (2)
C1	0.01468 (16)	0.74728 (13)	0.59708 (11)	0.0438 (2)
H1A	−0.0095	0.6464	0.5755	0.053*
C2	−0.11060 (16)	0.83699 (14)	0.64295 (12)	0.0449 (2)
H2A	−0.2193	0.7970	0.6513	0.054*
C3	−0.07179 (15)	0.98751 (13)	0.67639 (11)	0.0419 (2)
C4	0.08909 (16)	1.04825 (13)	0.65845 (13)	0.0469 (3)
H4A	0.1127	1.1494	0.6781	0.056*
C5	0.21342 (16)	0.96007 (14)	0.61205 (12)	0.0453 (3)
H5A	0.3207	1.0008	0.5999	0.054*
C6	0.17587 (15)	0.80817 (13)	0.58340 (10)	0.0405 (2)
C7	0.37903 (14)	0.63892 (12)	0.75909 (10)	0.0386 (2)
C8	0.38320 (15)	0.49001 (12)	0.75940 (10)	0.0396 (2)
H8A	0.4218	0.4280	0.6918	0.048*
C9	0.32790 (14)	0.43633 (12)	0.86381 (10)	0.0382 (2)
C10	0.2809 (2)	0.21991 (15)	0.95863 (13)	0.0563 (3)
C11	0.2140 (2)	0.31206 (16)	1.06288 (13)	0.0568 (3)
H11A	0.1724	0.2679	1.1282	0.068*
C12	0.20871 (17)	0.45853 (14)	1.07064 (11)	0.0458 (3)
C13	0.26811 (14)	0.52666 (12)	0.96685 (10)	0.0383 (2)
C14	0.26642 (17)	0.67727 (13)	0.96096 (11)	0.0452 (3)
H14A	0.2273	0.7400	1.0279	0.054*
C15	0.32143 (17)	0.73451 (13)	0.85815 (12)	0.0456 (3)
H15A	0.3200	0.8346	0.8552	0.055*
C16	0.1440 (2)	0.55079 (18)	1.18327 (12)	0.0630 (4)
H16A	0.1057	0.4884	1.2412	0.095*
H16B	0.0523	0.6035	1.1600	0.095*
H16C	0.2324	0.6196	1.2206	0.095*
C17	−0.34930 (19)	1.03035 (18)	0.74647 (17)	0.0627 (4)
H17A	−0.4167	1.1113	0.7733	0.094*
H17B	−0.3472	0.9685	0.8091	0.094*
H17C	−0.3963	0.9743	0.6714	0.094*

	U11	U22	U33	U12	U13	U23
S1	0.05261 (18)	0.04271 (16)	0.04015 (15)	0.00954 (12)	0.00695 (11)	0.00638 (11)
O1	0.0427 (4)	0.0443 (4)	0.0496 (4)	0.0032 (3)	0.0038 (3)	0.0114 (3)
O2	0.0732 (6)	0.0319 (4)	0.0456 (4)	0.0135 (4)	0.0032 (4)	0.0030 (3)
O3	0.0705 (7)	0.0656 (6)	0.0567 (6)	0.0191 (5)	0.0255 (5)	0.0214 (5)
O4	0.0723 (7)	0.0449 (5)	0.0543 (5)	0.0094 (4)	−0.0045 (5)	−0.0048 (4)
O5	0.1473 (13)	0.0369 (5)	0.0711 (7)	0.0192 (6)	0.0102 (8)	0.0137 (5)
O6	0.0477 (5)	0.0450 (5)	0.0759 (7)	0.0090 (4)	0.0043 (5)	0.0016 (4)
C1	0.0511 (6)	0.0349 (5)	0.0454 (6)	−0.0002 (4)	0.0022 (5)	0.0075 (4)
C2	0.0427 (6)	0.0412 (6)	0.0511 (6)	−0.0009 (4)	0.0028 (5)	0.0102 (5)
C3	0.0430 (6)	0.0389 (5)	0.0441 (5)	0.0059 (4)	−0.0030 (4)	0.0061 (4)
C4	0.0463 (6)	0.0352 (5)	0.0579 (7)	0.0003 (4)	−0.0065 (5)	0.0040 (5)
C5	0.0402 (6)	0.0405 (6)	0.0553 (7)	0.0000 (4)	−0.0021 (5)	0.0089 (5)
C6	0.0437 (6)	0.0388 (5)	0.0397 (5)	0.0051 (4)	0.0012 (4)	0.0078 (4)
C7	0.0389 (5)	0.0359 (5)	0.0413 (5)	0.0057 (4)	−0.0001 (4)	0.0056 (4)
C8	0.0437 (6)	0.0355 (5)	0.0391 (5)	0.0105 (4)	0.0016 (4)	0.0007 (4)
C9	0.0439 (5)	0.0312 (4)	0.0389 (5)	0.0093 (4)	−0.0034 (4)	0.0006 (4)
C10	0.0830 (10)	0.0385 (6)	0.0486 (7)	0.0097 (6)	−0.0028 (6)	0.0090 (5)
C11	0.0819 (10)	0.0480 (7)	0.0427 (6)	0.0087 (6)	0.0026 (6)	0.0121 (5)
C12	0.0549 (7)	0.0465 (6)	0.0354 (5)	0.0081 (5)	−0.0028 (5)	0.0029 (4)
C13	0.0436 (5)	0.0361 (5)	0.0342 (5)	0.0079 (4)	−0.0033 (4)	0.0000 (4)
C14	0.0578 (7)	0.0358 (5)	0.0400 (5)	0.0114 (5)	0.0008 (5)	−0.0039 (4)
C15	0.0572 (7)	0.0309 (5)	0.0480 (6)	0.0087 (5)	0.0001 (5)	0.0011 (4)
C16	0.0873 (11)	0.0628 (9)	0.0383 (6)	0.0128 (8)	0.0089 (6)	0.0021 (6)
C17	0.0479 (7)	0.0606 (9)	0.0819 (10)	0.0127 (6)	0.0117 (7)	0.0141 (7)

S1—O3	1.4203 (10)	C7—C8	1.3766 (15)
S1—O4	1.4210 (10)	C7—C15	1.3887 (16)
S1—O1	1.6076 (10)	C8—C9	1.3801 (16)
S1—C6	1.7401 (12)	C8—H8A	0.9300
O1—C7	1.4061 (14)	C9—C13	1.4011 (14)
O2—C9	1.3734 (13)	C10—C11	1.441 (2)
O2—C10	1.3760 (17)	C11—C12	1.3439 (19)
O5—C10	1.2018 (16)	C11—H11A	0.9300
O6—C3	1.3563 (15)	C12—C13	1.4509 (17)
O6—C17	1.4244 (18)	C12—C16	1.5011 (18)
C1—C6	1.3862 (17)	C13—C14	1.4017 (16)
C1—C2	1.3875 (18)	C14—C15	1.3796 (18)
C1—H1A	0.9300	C14—H14A	0.9300
C2—C3	1.3919 (17)	C15—H15A	0.9300
C2—H2A	0.9300	C16—H16A	0.9600
C3—C4	1.3924 (18)	C16—H16B	0.9600
C4—C5	1.3751 (18)	C16—H16C	0.9600
C4—H4A	0.9300	C17—H17A	0.9600
C5—C6	1.3979 (16)	C17—H17B	0.9600
C5—H5A	0.9300	C17—H17C	0.9600
O3—S1—O4	120.27 (7)	O2—C9—C8	115.88 (9)
O3—S1—O1	101.84 (6)	O2—C9—C13	121.43 (10)
O4—S1—O1	108.68 (6)	C8—C9—C13	122.69 (10)
O3—S1—C6	111.00 (6)	O5—C10—O2	116.70 (13)
O4—S1—C6	109.96 (6)	O5—C10—C11	126.35 (14)
O1—S1—C6	103.45 (5)	O2—C10—C11	116.95 (11)
C7—O1—S1	120.22 (7)	C12—C11—C10	123.40 (13)
C9—O2—C10	121.61 (10)	C12—C11—H11A	118.3
C3—O6—C17	118.18 (11)	C10—C11—H11A	118.3
C6—C1—C2	119.95 (11)	C11—C12—C13	118.25 (11)
C6—C1—H1A	120.0	C11—C12—C16	121.49 (12)
C2—C1—H1A	120.0	C13—C12—C16	120.26 (12)
C1—C2—C3	119.29 (11)	C9—C13—C14	117.23 (10)
C1—C2—H2A	120.4	C9—C13—C12	118.30 (10)
C3—C2—H2A	120.4	C14—C13—C12	124.45 (10)
O6—C3—C2	124.50 (11)	C15—C14—C13	121.51 (10)
O6—C3—C4	115.21 (11)	C15—C14—H14A	119.2
C2—C3—C4	120.28 (11)	C13—C14—H14A	119.2
C5—C4—C3	120.64 (11)	C14—C15—C7	118.37 (11)
C5—C4—H4A	119.7	C14—C15—H15A	120.8
C3—C4—H4A	119.7	C7—C15—H15A	120.8
C4—C5—C6	118.91 (11)	C12—C16—H16A	109.5
C4—C5—H5A	120.5	C12—C16—H16B	109.5
C6—C5—H5A	120.5	H16A—C16—H16B	109.5
C1—C6—C5	120.83 (11)	C12—C16—H16C	109.5
C1—C6—S1	120.13 (9)	H16A—C16—H16C	109.5
C5—C6—S1	119.00 (9)	H16B—C16—H16C	109.5
C8—C7—C15	122.74 (11)	O6—C17—H17A	109.5
C8—C7—O1	119.03 (10)	O6—C17—H17B	109.5
C15—C7—O1	118.06 (10)	H17A—C17—H17B	109.5
C7—C8—C9	117.46 (10)	O6—C17—H17C	109.5
C7—C8—H8A	121.3	H17A—C17—H17C	109.5
C9—C8—H8A	121.3	H17B—C17—H17C	109.5
O3—S1—O1—C7	−179.12 (8)	O1—C7—C8—C9	174.84 (10)
O4—S1—O1—C7	−51.20 (10)	C10—O2—C9—C8	−178.76 (12)
C6—S1—O1—C7	65.63 (9)	C10—O2—C9—C13	1.40 (19)
C6—C1—C2—C3	−0.89 (19)	C7—C8—C9—O2	−179.45 (10)
C17—O6—C3—C2	1.5 (2)	C7—C8—C9—C13	0.38 (18)
C17—O6—C3—C4	−179.69 (13)	C9—O2—C10—O5	−178.61 (15)
C1—C2—C3—O6	−178.23 (12)	C9—O2—C10—C11	0.7 (2)
C1—C2—C3—C4	3.04 (19)	O5—C10—C11—C12	176.67 (18)
O6—C3—C4—C5	178.64 (12)	O2—C10—C11—C12	−2.6 (2)
C2—C3—C4—C5	−2.5 (2)	C10—C11—C12—C13	2.2 (2)
C3—C4—C5—C6	−0.2 (2)	C10—C11—C12—C16	−177.60 (15)
C2—C1—C6—C5	−1.80 (19)	O2—C9—C13—C14	179.63 (11)
C2—C1—C6—S1	175.99 (9)	C8—C9—C13—C14	−0.20 (18)
C4—C5—C6—C1	2.33 (19)	O2—C9—C13—C12	−1.81 (17)
C4—C5—C6—S1	−175.49 (10)	C8—C9—C13—C12	178.37 (11)
O3—S1—C6—C1	145.04 (11)	C11—C12—C13—C9	0.03 (19)
O4—S1—C6—C1	9.50 (12)	C16—C12—C13—C9	179.81 (12)
O1—S1—C6—C1	−106.43 (10)	C11—C12—C13—C14	178.48 (13)
O3—S1—C6—C5	−37.13 (12)	C16—C12—C13—C14	−1.7 (2)
O4—S1—C6—C5	−172.67 (10)	C9—C13—C14—C15	−0.06 (18)
O1—S1—C6—C5	71.40 (10)	C12—C13—C14—C15	−178.53 (12)
S1—O1—C7—C8	83.63 (12)	C13—C14—C15—C7	0.1 (2)
S1—O1—C7—C15	−100.99 (12)	C8—C7—C15—C14	0.1 (2)
C15—C7—C8—C9	−0.32 (18)	O1—C7—C15—C14	−175.12 (11)

Cg1 is the centroid of the O2/C9–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O3i	0.93	2.50	3.4156 (16)	169
C15—H15A···O5ii	0.93	2.44	3.2923 (17)	153
C16—H16B···Cg1iii	0.96	2.96	3.8423 (17)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the O2/C9–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O3i	0.93	2.50	3.4156 (16)	169
C15—H15A⋯O5ii	0.93	2.44	3.2923 (17)	153
C16—H16B⋯Cg1iii	0.96	2.96	3.8423 (17)	154

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