4-Methyl-2-oxo-2,3-dihydro-1-benzopyran-7-yl benzene­sulfonate

Yang, S.-P.; Wang, D.-Q.; Han, L.-J.; Liu, Y.-F.

doi:10.1107/S1600536808032005

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2088

doi:10.1107/S1600536808032005

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4-Methyl-2-oxo-2,3-dihydro-1-benzopyran-7-yl benzenesulfonate

Shu-Ping Yang,^a ^* Da-Qi Wang,^b Li-Jun Han ^c and Yu-Fen Liu ^a

^aSchool of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, ^bCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China, and ^cSchool of Mathematics and Science, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China
^*Correspondence e-mail: yangshuping@hhit.edu.cn

(Received 30 September 2008; accepted 5 October 2008; online 9 October 2008)

The title compound, C₁₆H₁₂O₅S, 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, molecules 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_r = 316.32
Orthorhombic, P b c n
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.164
S = 1.09
2557 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) x, y-1, z.

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.

Supporting information

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

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

checkCIF report

Comment top

Coumarin derivatives exhibit a wide variety of pharmacological activities including anti-HIV (Xie et al., 2001), antibacterial (Tanitame et al., 2004), antioxidant (Shao et al., 1997), antithrombotic (Rendenbach-Müller et al., 1994) and antiinflammatory (Pochet et al., 1996) activities. We have recently reported the crystal structures of some coumarin derivatives (Yang et al., 2007, 2006). As part of our study of the crystal structures of coumarin derivatives, we report here the crystal structure of the title coumarin derivative.

The molecular structure is shown in Fig. 1. The dihedral angle between the coumarin ring system and the phenyl ring is 65.9 (1)°. The terminal S═O bond distances of 1.411 (3) and 1.421 (3) Å agree with 1.4207 (19) and 1.4331 (19) Å found in a related compound, 4-methyl-7-phenylsulfonamido-2H-1-benzopyran-2-one (Yang et al., 2007).

In the crystal the molecules are linked by weak C—H···O hydrogen bonding to form the ribbon structure (Table 1 and Fig. 2).

Related literature top

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 top

To an anhydrous pyridine solution (10 ml) of 7-hydroxy-4-methyl-coumarin (1.76 g, 10 mmol), a solution of phenylsulfonyl chloride (11 mmol) was slowly added at 278–283 K with stirring for 30 min. The reaction mixture was stirred continuously for 12 h at room temperature and then poured into ice–water (200 ml). The solid obtained was filtered off, washed with water and dried at room temperature. Colorless crystals of the title compound suitable for X-ray structure analysis were obtained by evaporation of an ethanol solution over a period of one week.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal structure of the title compound, showing the formation of a hydrogen-bonded R₃³(18) ribbon along [010]. For clarity, H atoms not involving in H-bonding have been omitted. Dashed lines indicate hydrogen bonds [Symmetry codes: (*) 1/2 - x, 1/2 + y, z; (#) 1/2 - x, -1/2 + y, z; (&) x, 1 + y, x; ($) x, -1 + y, z].

4-Methyl-2-oxo-2,3-dihydro-1-benzopyran-7-yl benzenesulfonate top

Crystal data top

C₁₆H₁₂O₅S	D_x = 1.445 Mg m⁻³
M_r = 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

Data collection top

Siemens SMART CCD area-detector diffractometer	2557 independent reflections
Radiation source: fine-focus sealed tube	1340 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −27→25
T_min = 0.892, T_max = 0.946	k = −6→10
11238 measured reflections	l = −16→15

Refinement top

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(F_o²) + (0.0635P)² + 1.4P] where P = (F_o² + 2F_c²)/3
2557 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₆H₁₂O₅S	V = 2908.8 (6) Å³
M_r = 316.32	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 23.319 (3) Å	µ = 0.24 mm⁻¹
b = 9.0865 (12) Å	T = 298 K
c = 13.7280 (17) Å	0.48 × 0.35 × 0.23 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	2557 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1340 reflections with I > 2σ(I)
T_min = 0.892, T_max = 0.946	R_int = 0.077
11238 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.09	Δρ_max = 0.21 e Å⁻³
2557 reflections	Δρ_min = −0.27 e Å⁻³
200 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y+1/2, z; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂O₅S
M_r	316.32
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	23.319 (3), 9.0865 (12), 13.7280 (17)
V (Å³)	2908.8 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.48 × 0.35 × 0.23

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.892, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	11238, 2557, 1340
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.164, 1.09
No. of reflections	2557
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.27

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O4ⁱ	0.93	2.43	3.325 (4)	162.7
C8—H8···O2ⁱⁱ	0.93	2.48	3.293 (5)	145.4

Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) x, y−1, z.

Acknowledgements

The authors acknowledge the financial support of the Technology Science Foundation of Huaihai Institute of Technology, China.

References

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