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

In the asymmetric unit of the title compound, C(16)H(11)FO(5)S, the 2H-chromene ring is essentially planar, with a maximum deviation of 0.040 (2) Å. The dihedral angle between the 2H-chromene ring and the 4-fluoro-phenyl ring is 2.17 (8)°. One of the sulfonamide O atoms is approximately coplanar with the benzene ring [C-C-S-O torsion angle = 166.00 (14)°], whereas the other O atom lies well below the plane [C-C-S-O = -61.35 (17)°]. In the crystal, mol-ecules are connected by weak C-H⋯O hydrogen bonds, forming two-dimensional networks parallel to the ac plane.

Related literature

For details and applications of coumarines, see: Gu et al. (2007 ▶); Wrobel et al. (2002 ▶); Kostova (2005 ▶). For related structures, see: Sinha et al. (2011 ▶); Al-Najjar et al. (2012 ▶). For the synthetic procedure, see: Sinha et al. (2011 ▶); Fusegi et al. (2009 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H11FO5S

M = 334.31

Monoclinic,

a = 17.2983 (4) Å

b = 5.3397 (1) Å

c = 17.1669 (4) Å

β = 118.195 (1)°

V = 1397.52 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.36 × 0.19 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.911, T max = 0.959

26795 measured reflections

4303 independent reflections

3494 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.156

S = 1.04

4303 reflections

209 parameters

H-atom parameters constrained

Δρmax = 1.14 e Å−3

Δρmin = −0.72 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, a. DOI: 10.1107/S1600536812004394/rz2704sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004394/rz2704Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004394/rz2704Isup3.cml

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

C16H11FO5S	F(000) = 688
Mr = 334.31	Dx = 1.589 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9952 reflections
a = 17.2983 (4) Å	θ = 2.4–30.6°
b = 5.3397 (1) Å	µ = 0.27 mm−1
c = 17.1669 (4) Å	T = 100 K
β = 118.195 (1)°	Block, colourless
V = 1397.52 (5) Å3	0.36 × 0.19 × 0.16 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4303 independent reflections
Radiation source: fine-focus sealed tube	3494 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
φ and ω scans	θmax = 30.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −24→24
Tmin = 0.911, Tmax = 0.959	k = −7→7
26795 measured reflections	l = −24→24

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0914P)2 + 0.9651P] where P = (Fo2 + 2Fc2)/3
4303 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 1.14 e Å−3
0 restraints	Δρmin = −0.72 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.05985 (3)	0.71221 (8)	0.40375 (3)	0.01356 (13)
F1	0.39345 (8)	0.2691 (3)	0.47175 (9)	0.0276 (3)
O1	0.00823 (8)	0.4700 (3)	0.40935 (9)	0.0161 (3)
O2	−0.26376 (8)	0.8084 (3)	0.36579 (9)	0.0161 (3)
O3	0.01710 (9)	0.8017 (3)	0.31455 (9)	0.0187 (3)
O4	0.07250 (9)	0.8822 (3)	0.47276 (9)	0.0207 (3)
O5	−0.38605 (9)	0.9692 (3)	0.35461 (9)	0.0222 (3)
C1	0.15987 (12)	0.3544 (4)	0.38064 (12)	0.0163 (4)
H1A	0.1064	0.2816	0.3380	0.020*
C2	0.23997 (13)	0.2524 (4)	0.39694 (13)	0.0182 (4)
H2A	0.2424	0.1061	0.3667	0.022*
C3	0.31602 (12)	0.3684 (4)	0.45807 (13)	0.0187 (4)
C4	0.31704 (12)	0.5773 (4)	0.50573 (13)	0.0188 (4)
H4A	0.3708	0.6504	0.5476	0.023*
C5	0.23669 (12)	0.6784 (4)	0.49075 (12)	0.0163 (4)
H5A	0.2346	0.8214	0.5227	0.020*
C6	0.15971 (11)	0.5657 (3)	0.42815 (12)	0.0140 (3)
C7	−0.08408 (11)	0.4728 (3)	0.36472 (12)	0.0139 (3)
C8	−0.12939 (11)	0.6500 (4)	0.38628 (12)	0.0147 (3)
H8A	−0.0998	0.7771	0.4288	0.018*
C9	−0.22037 (11)	0.6323 (3)	0.34251 (12)	0.0139 (3)
C10	−0.35402 (12)	0.8098 (4)	0.32803 (13)	0.0169 (4)
C11	−0.40187 (12)	0.6269 (4)	0.25971 (12)	0.0177 (4)
H11A	−0.4642	0.6291	0.2315	0.021*
C12	−0.36115 (12)	0.4529 (4)	0.23449 (12)	0.0156 (3)
C13	−0.26579 (12)	0.4483 (4)	0.27933 (12)	0.0146 (3)
C14	−0.21569 (12)	0.2714 (4)	0.26141 (12)	0.0160 (4)
H14A	−0.2447	0.1423	0.2196	0.019*
C15	−0.12520 (12)	0.2829 (4)	0.30367 (12)	0.0157 (3)
H15A	−0.0918	0.1634	0.2912	0.019*
C16	−0.41273 (13)	0.2751 (4)	0.16052 (14)	0.0209 (4)
H16A	−0.4755	0.2979	0.1408	0.031*
H16B	−0.3959	0.1027	0.1811	0.031*
H16C	−0.4006	0.3084	0.1112	0.031*

	U11	U22	U33	U12	U13	U23
S1	0.0139 (2)	0.0141 (2)	0.0135 (2)	0.00107 (14)	0.00718 (18)	0.00011 (15)
F1	0.0170 (6)	0.0382 (8)	0.0280 (7)	0.0093 (5)	0.0110 (5)	0.0014 (6)
O1	0.0137 (6)	0.0158 (6)	0.0191 (7)	0.0007 (5)	0.0079 (5)	0.0029 (5)
O2	0.0129 (6)	0.0189 (7)	0.0170 (6)	0.0011 (5)	0.0075 (5)	−0.0029 (5)
O3	0.0185 (7)	0.0217 (7)	0.0162 (7)	0.0037 (5)	0.0085 (6)	0.0058 (5)
O4	0.0216 (7)	0.0206 (7)	0.0213 (7)	0.0000 (5)	0.0111 (6)	−0.0068 (6)
O5	0.0172 (6)	0.0259 (8)	0.0236 (7)	0.0024 (5)	0.0098 (6)	−0.0048 (6)
C1	0.0182 (9)	0.0188 (9)	0.0127 (8)	0.0001 (7)	0.0079 (7)	−0.0002 (7)
C2	0.0211 (9)	0.0192 (9)	0.0170 (9)	0.0033 (7)	0.0112 (8)	0.0010 (7)
C3	0.0140 (8)	0.0264 (10)	0.0171 (9)	0.0053 (7)	0.0085 (7)	0.0041 (8)
C4	0.0139 (8)	0.0240 (10)	0.0172 (9)	−0.0004 (7)	0.0063 (7)	0.0011 (7)
C5	0.0167 (8)	0.0182 (9)	0.0141 (8)	−0.0005 (6)	0.0074 (7)	0.0002 (7)
C6	0.0134 (8)	0.0170 (8)	0.0119 (8)	0.0012 (6)	0.0063 (7)	0.0005 (6)
C7	0.0135 (8)	0.0158 (8)	0.0126 (8)	0.0012 (6)	0.0064 (7)	0.0032 (6)
C8	0.0154 (8)	0.0165 (8)	0.0131 (8)	−0.0004 (6)	0.0073 (7)	−0.0007 (7)
C9	0.0147 (8)	0.0152 (8)	0.0134 (8)	0.0006 (6)	0.0080 (7)	0.0006 (6)
C10	0.0142 (8)	0.0213 (9)	0.0161 (9)	0.0014 (6)	0.0079 (7)	0.0011 (7)
C11	0.0130 (8)	0.0225 (9)	0.0162 (9)	−0.0020 (7)	0.0059 (7)	−0.0015 (7)
C12	0.0163 (8)	0.0192 (9)	0.0118 (8)	−0.0023 (6)	0.0069 (7)	−0.0003 (7)
C13	0.0168 (8)	0.0161 (8)	0.0123 (8)	−0.0004 (6)	0.0079 (7)	0.0005 (6)
C14	0.0196 (9)	0.0157 (8)	0.0134 (8)	−0.0007 (6)	0.0084 (7)	−0.0014 (6)
C15	0.0201 (9)	0.0152 (8)	0.0141 (8)	0.0011 (6)	0.0101 (7)	−0.0004 (6)
C16	0.0186 (9)	0.0232 (10)	0.0189 (9)	−0.0044 (7)	0.0071 (8)	−0.0046 (7)

S1—O4	1.4249 (14)	C5—H5A	0.9500
S1—O3	1.4318 (14)	C7—C8	1.386 (2)
S1—O1	1.6003 (14)	C7—C15	1.389 (3)
S1—C6	1.7572 (18)	C8—C9	1.390 (2)
F1—C3	1.354 (2)	C8—H8A	0.9500
O1—C7	1.407 (2)	C9—C13	1.398 (3)
O2—C9	1.375 (2)	C10—C11	1.448 (3)
O2—C10	1.379 (2)	C11—C12	1.355 (3)
O5—C10	1.216 (2)	C11—H11A	0.9500
C1—C2	1.389 (3)	C12—C13	1.454 (2)
C1—C6	1.393 (3)	C12—C16	1.496 (3)
C1—H1A	0.9500	C13—C14	1.411 (2)
C2—C3	1.382 (3)	C14—C15	1.381 (3)
C2—H2A	0.9500	C14—H14A	0.9500
C3—C4	1.379 (3)	C15—H15A	0.9500
C4—C5	1.397 (3)	C16—H16A	0.9800
C4—H4A	0.9500	C16—H16B	0.9800
C5—C6	1.392 (3)	C16—H16C	0.9800
O4—S1—O3	118.38 (9)	C7—C8—H8A	121.7
O4—S1—O1	109.63 (8)	C9—C8—H8A	121.7
O3—S1—O1	108.24 (8)	O2—C9—C8	115.48 (16)
O4—S1—C6	109.75 (9)	O2—C9—C13	121.48 (15)
O3—S1—C6	110.88 (8)	C8—C9—C13	123.03 (16)
O1—S1—C6	98.01 (8)	O5—C10—O2	116.29 (17)
C7—O1—S1	118.71 (11)	O5—C10—C11	126.04 (17)
C9—O2—C10	121.29 (15)	O2—C10—C11	117.66 (16)
C2—C1—C6	118.51 (18)	C12—C11—C10	122.46 (17)
C2—C1—H1A	120.7	C12—C11—H11A	118.8
C6—C1—H1A	120.7	C10—C11—H11A	118.8
C3—C2—C1	118.60 (18)	C11—C12—C13	118.27 (17)
C3—C2—H2A	120.7	C11—C12—C16	120.97 (17)
C1—C2—H2A	120.7	C13—C12—C16	120.73 (16)
F1—C3—C4	118.67 (18)	C9—C13—C14	117.50 (16)
F1—C3—C2	117.72 (18)	C9—C13—C12	118.70 (16)
C4—C3—C2	123.61 (17)	C14—C13—C12	123.79 (17)
C3—C4—C5	118.10 (18)	C15—C14—C13	121.10 (17)
C3—C4—H4A	121.0	C15—C14—H14A	119.4
C5—C4—H4A	120.9	C13—C14—H14A	119.4
C6—C5—C4	118.71 (18)	C14—C15—C7	118.56 (16)
C6—C5—H5A	120.6	C14—C15—H15A	120.7
C4—C5—H5A	120.6	C7—C15—H15A	120.7
C5—C6—C1	122.44 (16)	C12—C16—H16A	109.5
C5—C6—S1	117.74 (14)	C12—C16—H16B	109.5
C1—C6—S1	119.65 (14)	H16A—C16—H16B	109.5
C8—C7—C15	123.20 (16)	C12—C16—H16C	109.5
C8—C7—O1	120.08 (16)	H16A—C16—H16C	109.5
C15—C7—O1	116.60 (15)	H16B—C16—H16C	109.5
C7—C8—C9	116.60 (17)
O4—S1—O1—C7	88.16 (14)	C10—O2—C9—C8	−179.26 (16)
O3—S1—O1—C7	−42.30 (14)	C10—O2—C9—C13	0.4 (3)
C6—S1—O1—C7	−157.48 (13)	C7—C8—C9—O2	179.28 (15)
C6—C1—C2—C3	−1.5 (3)	C7—C8—C9—C13	−0.3 (3)
C1—C2—C3—F1	−178.69 (17)	C9—O2—C10—O5	178.24 (17)
C1—C2—C3—C4	1.7 (3)	C9—O2—C10—C11	−3.0 (2)
F1—C3—C4—C5	179.75 (17)	O5—C10—C11—C12	−179.18 (19)
C2—C3—C4—C5	−0.6 (3)	O2—C10—C11—C12	2.2 (3)
C3—C4—C5—C6	−0.6 (3)	C10—C11—C12—C13	1.2 (3)
C4—C5—C6—C1	0.7 (3)	C10—C11—C12—C16	−176.90 (18)
C4—C5—C6—S1	−174.62 (14)	O2—C9—C13—C14	−178.34 (16)
C2—C1—C6—C5	0.4 (3)	C8—C9—C13—C14	1.3 (3)
C2—C1—C6—S1	175.59 (14)	O2—C9—C13—C12	3.1 (3)
O4—S1—C6—C5	−18.55 (17)	C8—C9—C13—C12	−177.28 (17)
O3—S1—C6—C5	114.09 (15)	C11—C12—C13—C9	−3.8 (3)
O1—S1—C6—C5	−132.82 (15)	C16—C12—C13—C9	174.28 (17)
O4—S1—C6—C1	166.00 (14)	C11—C12—C13—C14	177.74 (18)
O3—S1—C6—C1	−61.35 (17)	C16—C12—C13—C14	−4.2 (3)
O1—S1—C6—C1	51.73 (16)	C9—C13—C14—C15	−1.1 (3)
S1—O1—C7—C8	−60.4 (2)	C12—C13—C14—C15	177.33 (17)
S1—O1—C7—C15	123.36 (15)	C13—C14—C15—C7	0.1 (3)
C15—C7—C8—C9	−0.8 (3)	C8—C7—C15—C14	0.9 (3)
O1—C7—C8—C9	−176.72 (15)	O1—C7—C15—C14	176.96 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O3i	0.95	2.48	3.314 (2)	147
C4—H4A···O5ii	0.95	2.57	3.214 (3)	126
C8—H8A···O4ii	0.95	2.37	3.288 (3)	162
C11—H11A···O5iii	0.95	2.45	3.349 (3)	158
C15—H15A···O3iv	0.95	2.59	3.502 (3)	160
C16—H16A···O5iii	0.98	2.60	3.522 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O3i	0.95	2.48	3.314 (2)	147
C4—H4A⋯O5ii	0.95	2.57	3.214 (3)	126
C8—H8A⋯O4ii	0.95	2.37	3.288 (3)	162
C11—H11A⋯O5iii	0.95	2.45	3.349 (3)	158
C15—H15A⋯O3iv	0.95	2.59	3.502 (3)	160
C16—H16A⋯O5iii	0.98	2.60	3.522 (3)	157

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