2-(5,7-Dimeth-oxy-4-oxo-4H-chromen-2-yl)phenyl 4-toluene-sulfonate.

In the crystal structure of the title compound, C(24)H(20)O(7)S, the chromone system makes a dihedral angle of 37.32 (7)° with the adjacent benzene ring. The chromone ring system and the tolyl ring are almost parallel, with a dihedral angle of 4.56 (9)°. The tolyl ring is twisted at an angle of 41.75 (6)° with respect to the benzene ring. Weak intra- and inter-molecular C-H⋯O inter-actions are observed.

Related literature

For related literature, see: Chenera et al. (1993 ▶); Ellis (1997 ▶); Kang et al. (2004 ▶); Kooijman et al. (1984 ▶); Marx et al. (2007 ▶); Puviarasan et al. (1998 ▶).

Experimental

Crystal data

C24H20O7S

M = 452.46

Monoclinic,

a = 7.373 (2) Å

b = 21.011 (6) Å

c = 13.969 (4) Å

β = 98.972 (5)°

V = 2137.6 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 295 (2) K

0.22 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.958, T max = 0.969

24478 measured reflections

5093 independent reflections

3932 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.126

S = 1.05

5093 reflections

292 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022654/is2315sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022654/is2315Isup2.hkl

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

C24H20O7S	F000 = 944
Mr = 452.46	Dx = 1.406 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5023 reflections
a = 7.373 (2) Å	θ = 1.7–28.0º
b = 21.011 (6) Å	µ = 0.20 mm−1
c = 13.969 (4) Å	T = 295 (2) K
β = 98.972 (5)º	Block, colourless
V = 2137.6 (10) Å3	0.22 × 0.18 × 0.16 mm
Z = 4

Bruker Kappa APEXII diffractometer	5093 independent reflections
Radiation source: fine-focus sealed tube	3932 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
T = 295(2) K	θmax = 28.0º
ω and φ scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.958, Tmax = 0.969	k = −27→27
24478 measured reflections	l = −17→18

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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.0523P)2 + 0.7841P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
5093 reflections	Δρmax = 0.27 e Å−3
292 parameters	Δρmin = −0.38 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
S1	0.08488 (8)	0.62413 (2)	0.64071 (4)	0.05905 (18)
O1	0.0797 (3)	0.61918 (9)	0.74090 (14)	0.0966 (7)
O2	−0.0424 (2)	0.58983 (7)	0.57276 (15)	0.0778 (5)
O3	0.28958 (18)	0.59915 (6)	0.63318 (9)	0.0471 (3)
O4	0.53667 (17)	0.74321 (5)	0.50458 (8)	0.0405 (3)
O5	0.7115 (2)	0.75407 (7)	0.79509 (10)	0.0666 (4)
O6	0.6757 (3)	0.95793 (6)	0.44864 (11)	0.0699 (5)
O7	0.8015 (2)	0.87641 (7)	0.76660 (9)	0.0541 (4)
C1	0.0892 (3)	0.70374 (9)	0.60523 (15)	0.0476 (5)
C2	0.1605 (3)	0.74935 (10)	0.67212 (18)	0.0602 (5)
H2	0.1973	0.7387	0.7368	0.072*
C3	0.1758 (3)	0.81123 (10)	0.6404 (2)	0.0666 (6)
H3	0.2228	0.8423	0.6848	0.080*
C4	0.1234 (3)	0.82809 (10)	0.5447 (2)	0.0651 (6)
C5	0.0488 (3)	0.78228 (11)	0.48044 (18)	0.0630 (6)
H5	0.0092	0.7933	0.4161	0.076*
C6	0.0313 (3)	0.71989 (10)	0.50952 (16)	0.0556 (5)
H6	−0.0188	0.6892	0.4651	0.067*
C7	0.1486 (4)	0.89585 (12)	0.5117 (3)	0.0992 (11)
H7A	0.1668	0.8957	0.4451	0.149*
H7B	0.2537	0.9144	0.5510	0.149*
H7C	0.0412	0.9203	0.5180	0.149*
C8	0.3393 (2)	0.59138 (7)	0.54037 (12)	0.0373 (4)
C9	0.2781 (2)	0.53817 (8)	0.48695 (14)	0.0430 (4)
H9	0.2039	0.5085	0.5116	0.052*
C10	0.3279 (3)	0.52929 (9)	0.39678 (14)	0.0462 (4)
H10	0.2886	0.4933	0.3606	0.055*
C11	0.4361 (3)	0.57390 (9)	0.36046 (14)	0.0468 (4)
H11	0.4669	0.5684	0.2989	0.056*
C12	0.4992 (3)	0.62672 (8)	0.41444 (13)	0.0427 (4)
H12	0.5727	0.6563	0.3890	0.051*
C13	0.4541 (2)	0.63623 (8)	0.50660 (12)	0.0363 (4)
C14	0.5303 (2)	0.69218 (7)	0.56371 (12)	0.0355 (4)
C15	0.6059 (2)	0.79985 (7)	0.54323 (12)	0.0355 (4)
C16	0.6061 (3)	0.84733 (8)	0.47443 (13)	0.0431 (4)
H16	0.5662	0.8395	0.4090	0.052*
C17	0.6678 (3)	0.90651 (8)	0.50682 (14)	0.0464 (4)
C18	0.7306 (3)	0.91772 (9)	0.60496 (14)	0.0463 (4)
H18	0.7697	0.9583	0.6255	0.056*
C19	0.7350 (2)	0.86942 (8)	0.67109 (13)	0.0399 (4)
C20	0.6689 (2)	0.80742 (8)	0.64181 (12)	0.0352 (4)
C21	0.6642 (3)	0.75290 (8)	0.70711 (13)	0.0416 (4)
C22	0.5923 (3)	0.69490 (8)	0.65831 (13)	0.0425 (4)
H22	0.5895	0.6581	0.6949	0.051*
C23	0.6289 (5)	0.94826 (13)	0.34712 (18)	0.1037 (12)
H23A	0.7102	0.9173	0.3263	0.156*
H23B	0.6402	0.9877	0.3139	0.156*
H23C	0.5047	0.9332	0.3326	0.156*
C24	0.8834 (4)	0.93587 (12)	0.79739 (17)	0.0718 (7)
H24A	0.9837	0.9443	0.7628	0.108*
H24B	0.9282	0.9343	0.8657	0.108*
H24C	0.7936	0.9691	0.7844	0.108*

	U11	U22	U33	U12	U13	U23
S1	0.0666 (3)	0.0429 (3)	0.0766 (4)	−0.0102 (2)	0.0393 (3)	−0.0010 (2)
O1	0.1372 (18)	0.0811 (12)	0.0899 (13)	0.0014 (12)	0.0750 (13)	0.0146 (10)
O2	0.0545 (9)	0.0495 (9)	0.1352 (16)	−0.0205 (7)	0.0327 (9)	−0.0202 (9)
O3	0.0596 (8)	0.0376 (7)	0.0469 (7)	−0.0034 (6)	0.0164 (6)	0.0059 (5)
O4	0.0558 (8)	0.0302 (6)	0.0347 (6)	−0.0089 (5)	0.0051 (5)	−0.0008 (5)
O5	0.1040 (13)	0.0593 (9)	0.0336 (7)	−0.0095 (8)	0.0011 (7)	−0.0001 (6)
O6	0.1180 (14)	0.0340 (7)	0.0570 (9)	−0.0143 (8)	0.0117 (9)	0.0049 (6)
O7	0.0637 (9)	0.0567 (8)	0.0416 (7)	−0.0160 (7)	0.0071 (6)	−0.0158 (6)
C1	0.0453 (10)	0.0370 (9)	0.0641 (13)	−0.0033 (8)	0.0197 (9)	−0.0086 (8)
C2	0.0599 (13)	0.0533 (12)	0.0673 (14)	0.0019 (10)	0.0098 (10)	−0.0162 (10)
C3	0.0526 (12)	0.0453 (12)	0.1012 (14)	−0.0042 (9)	0.0095 (12)	−0.0269 (11)
C4	0.0437 (11)	0.0445 (11)	0.1110 (15)	0.0029 (9)	0.0248 (11)	0.0005 (12)
C5	0.0588 (13)	0.0569 (13)	0.0756 (15)	0.0076 (10)	0.0176 (11)	0.0057 (11)
C6	0.0522 (12)	0.0483 (11)	0.0675 (14)	−0.0034 (9)	0.0130 (10)	−0.0119 (10)
C7	0.0805 (18)	0.0483 (14)	0.179 (3)	0.0009 (13)	0.054 (2)	0.0132 (17)
C8	0.0411 (9)	0.0301 (8)	0.0408 (9)	0.0028 (7)	0.0066 (7)	0.0045 (7)
C9	0.0416 (9)	0.0295 (8)	0.0569 (11)	−0.0021 (7)	0.0046 (8)	0.0035 (7)
C10	0.0445 (10)	0.0349 (9)	0.0569 (11)	−0.0015 (7)	0.0004 (8)	−0.0103 (8)
C11	0.0493 (11)	0.0479 (10)	0.0434 (10)	−0.0011 (8)	0.0081 (8)	−0.0098 (8)
C12	0.0464 (10)	0.0375 (9)	0.0457 (10)	−0.0055 (7)	0.0113 (8)	−0.0018 (7)
C13	0.0381 (9)	0.0298 (8)	0.0407 (9)	−0.0002 (6)	0.0051 (7)	−0.0001 (7)
C14	0.0385 (9)	0.0307 (8)	0.0384 (9)	−0.0018 (6)	0.0099 (7)	0.0018 (6)
C15	0.0384 (9)	0.0303 (8)	0.0388 (9)	−0.0031 (6)	0.0090 (7)	−0.0047 (7)
C16	0.0567 (11)	0.0361 (9)	0.0360 (9)	−0.0053 (8)	0.0055 (8)	−0.0011 (7)
C17	0.0577 (11)	0.0334 (9)	0.0497 (11)	−0.0048 (8)	0.0134 (9)	0.0008 (8)
C18	0.0532 (11)	0.0342 (9)	0.0538 (11)	−0.0094 (8)	0.0152 (9)	−0.0120 (8)
C19	0.0378 (9)	0.0427 (9)	0.0409 (9)	−0.0039 (7)	0.0115 (7)	−0.0106 (7)
C20	0.0348 (8)	0.0369 (8)	0.0352 (8)	−0.0023 (6)	0.0094 (6)	−0.0047 (7)
C21	0.0455 (10)	0.0437 (10)	0.0359 (9)	−0.0012 (8)	0.0073 (7)	−0.0010 (7)
C22	0.0511 (10)	0.0357 (9)	0.0409 (10)	−0.0031 (7)	0.0080 (8)	0.0048 (7)
C23	0.196 (4)	0.0525 (14)	0.0567 (15)	−0.0225 (18)	0.0020 (18)	0.0179 (12)
C24	0.0765 (16)	0.0766 (16)	0.0605 (14)	−0.0301 (13)	0.0054 (12)	−0.0266 (12)

S1—O1	1.4099 (19)	C9—C10	1.379 (3)
S1—O2	1.4226 (18)	C9—H9	0.9300
S1—O3	1.6168 (15)	C10—C11	1.378 (3)
S1—C1	1.746 (2)	C10—H10	0.9300
O3—C8	1.411 (2)	C11—C12	1.381 (3)
O4—C14	1.3588 (19)	C11—H11	0.9300
O4—C15	1.3720 (19)	C12—C13	1.394 (2)
O5—C21	1.224 (2)	C12—H12	0.9300
O6—C17	1.359 (2)	C13—C14	1.481 (2)
O6—C23	1.421 (3)	C14—C22	1.331 (2)
O7—C19	1.356 (2)	C15—C16	1.385 (2)
O7—C24	1.425 (2)	C15—C20	1.392 (2)
C1—C6	1.381 (3)	C16—C17	1.376 (2)
C1—C2	1.384 (3)	C16—H16	0.9300
C2—C3	1.384 (3)	C17—C18	1.397 (3)
C2—H2	0.9300	C18—C19	1.369 (3)
C3—C4	1.378 (4)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.428 (2)
C4—C5	1.372 (3)	C20—C21	1.468 (2)
C4—C7	1.517 (3)	C21—C22	1.455 (2)
C5—C6	1.384 (3)	C22—H22	0.9300
C5—H5	0.9300	C23—H23A	0.9600
C6—H6	0.9300	C23—H23B	0.9600
C7—H7A	0.9600	C23—H23C	0.9600
C7—H7B	0.9600	C24—H24A	0.9600
C7—H7C	0.9600	C24—H24B	0.9600
C8—C9	1.380 (2)	C24—H24C	0.9600
C8—C13	1.397 (2)
O1—S1—O2	120.53 (12)	C11—C12—C13	120.71 (16)
O1—S1—O3	102.15 (11)	C11—C12—H12	119.6
O2—S1—O3	108.53 (9)	C13—C12—H12	119.6
O1—S1—C1	110.91 (11)	C12—C13—C8	117.38 (15)
O2—S1—C1	109.59 (11)	C12—C13—C14	119.07 (15)
O3—S1—C1	103.52 (8)	C8—C13—C14	123.54 (15)
C8—O3—S1	118.44 (11)	C22—C14—O4	122.06 (15)
C14—O4—C15	119.42 (13)	C22—C14—C13	127.71 (15)
C17—O6—C23	117.19 (16)	O4—C14—C13	110.19 (14)
C19—O7—C24	117.60 (16)	O4—C15—C16	113.08 (14)
C6—C1—C2	120.7 (2)	O4—C15—C20	122.33 (14)
C6—C1—S1	119.57 (15)	C16—C15—C20	124.59 (15)
C2—C1—S1	119.57 (17)	C17—C16—C15	117.29 (16)
C1—C2—C3	118.4 (2)	C17—C16—H16	121.4
C1—C2—H2	120.8	C15—C16—H16	121.4
C3—C2—H2	120.8	O6—C17—C16	124.38 (17)
C4—C3—C2	121.8 (2)	O6—C17—C18	114.47 (16)
C4—C3—H3	119.1	C16—C17—C18	121.14 (17)
C2—C3—H3	119.1	C19—C18—C17	120.43 (16)
C5—C4—C3	118.5 (2)	C19—C18—H18	119.8
C5—C4—C7	121.0 (3)	C17—C18—H18	119.8
C3—C4—C7	120.5 (3)	O7—C19—C18	123.41 (16)
C4—C5—C6	121.2 (2)	O7—C19—C20	115.82 (16)
C4—C5—H5	119.4	C18—C19—C20	120.77 (16)
C6—C5—H5	119.4	C15—C20—C19	115.71 (15)
C1—C6—C5	119.2 (2)	C15—C20—C21	119.27 (15)
C1—C6—H6	120.4	C19—C20—C21	125.01 (15)
C5—C6—H6	120.4	O5—C21—C22	120.86 (17)
C4—C7—H7A	109.5	O5—C21—C20	125.27 (17)
C4—C7—H7B	109.5	C22—C21—C20	113.86 (15)
H7A—C7—H7B	109.5	C14—C22—C21	123.01 (16)
C4—C7—H7C	109.5	C14—C22—H22	118.5
H7A—C7—H7C	109.5	C21—C22—H22	118.5
H7B—C7—H7C	109.5	O6—C23—H23A	109.5
C9—C8—C13	121.86 (16)	O6—C23—H23B	109.5
C9—C8—O3	118.74 (15)	H23A—C23—H23B	109.5
C13—C8—O3	119.35 (14)	O6—C23—H23C	109.5
C10—C9—C8	119.51 (16)	H23A—C23—H23C	109.5
C10—C9—H9	120.2	H23B—C23—H23C	109.5
C8—C9—H9	120.2	O7—C24—H24A	109.5
C11—C10—C9	119.76 (16)	O7—C24—H24B	109.5
C11—C10—H10	120.1	H24A—C24—H24B	109.5
C9—C10—H10	120.1	O7—C24—H24C	109.5
C10—C11—C12	120.73 (17)	H24A—C24—H24C	109.5
C10—C11—H11	119.6	H24B—C24—H24C	109.5
C12—C11—H11	119.6
O1—S1—O3—C8	173.84 (13)	C12—C13—C14—C22	−140.30 (19)
O2—S1—O3—C8	45.51 (14)	C8—C13—C14—C22	39.1 (3)
C1—S1—O3—C8	−70.87 (13)	C12—C13—C14—O4	37.4 (2)
O1—S1—C1—C6	−157.58 (18)	C8—C13—C14—O4	−143.28 (16)
O2—S1—C1—C6	−22.09 (19)	C14—O4—C15—C16	179.20 (15)
O3—S1—C1—C6	93.54 (17)	C14—O4—C15—C20	−0.6 (2)
O1—S1—C1—C2	26.1 (2)	O4—C15—C16—C17	178.01 (16)
O2—S1—C1—C2	161.64 (16)	C20—C15—C16—C17	−2.2 (3)
O3—S1—C1—C2	−82.74 (17)	C23—O6—C17—C16	−4.5 (3)
C6—C1—C2—C3	−1.3 (3)	C23—O6—C17—C18	174.7 (2)
S1—C1—C2—C3	174.95 (16)	C15—C16—C17—O6	−179.71 (19)
C1—C2—C3—C4	−0.4 (3)	C15—C16—C17—C18	1.1 (3)
C2—C3—C4—C5	2.1 (3)	O6—C17—C18—C19	−178.11 (18)
C2—C3—C4—C7	−177.7 (2)	C16—C17—C18—C19	1.1 (3)
C3—C4—C5—C6	−2.1 (3)	C24—O7—C19—C18	−5.0 (3)
C7—C4—C5—C6	177.7 (2)	C24—O7—C19—C20	174.65 (18)
C2—C1—C6—C5	1.3 (3)	C17—C18—C19—O7	177.12 (17)
S1—C1—C6—C5	−174.92 (16)	C17—C18—C19—C20	−2.5 (3)
C4—C5—C6—C1	0.4 (3)	O4—C15—C20—C19	−179.33 (15)
S1—O3—C8—C9	−77.99 (17)	C16—C15—C20—C19	0.9 (2)
S1—O3—C8—C13	104.39 (16)	O4—C15—C20—C21	0.9 (2)
C13—C8—C9—C10	−1.4 (3)	C16—C15—C20—C21	−178.93 (17)
O3—C8—C9—C10	−178.93 (15)	O7—C19—C20—C15	−178.12 (15)
C8—C9—C10—C11	−0.8 (3)	C18—C19—C20—C15	1.5 (2)
C9—C10—C11—C12	1.7 (3)	O7—C19—C20—C21	1.6 (2)
C10—C11—C12—C13	−0.4 (3)	C18—C19—C20—C21	−178.72 (17)
C11—C12—C13—C8	−1.7 (3)	C15—C20—C21—O5	−178.16 (19)
C11—C12—C13—C14	177.69 (16)	C19—C20—C21—O5	2.1 (3)
C9—C8—C13—C12	2.6 (3)	C15—C20—C21—C22	0.5 (2)
O3—C8—C13—C12	−179.87 (15)	C19—C20—C21—C22	−179.25 (16)
C9—C8—C13—C14	−176.78 (16)	O4—C14—C22—C21	2.8 (3)
O3—C8—C13—C14	0.8 (2)	C13—C14—C22—C21	−179.82 (17)
C15—O4—C14—C22	−1.2 (2)	O5—C21—C22—C14	176.42 (19)
C15—O4—C14—C13	−179.02 (13)	C20—C21—C22—C14	−2.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.93	2.59	2.949 (3)	103
C22—H22···O3	0.93	2.56	2.985 (2)	108
C9—H9···O2i	0.93	2.58	3.240 (2)	129
C12—H12···O5ii	0.93	2.60	3.510 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2	0.93	2.59	2.949 (3)	103
C22—H22⋯O3	0.93	2.56	2.985 (2)	108
C9—H9⋯O2i	0.93	2.58	3.240 (2)	129
C12—H12⋯O5ii	0.93	2.60	3.510 (2)	168

Symmetry codes: (i) ; (ii) .