N-(2,3-Dihydro-1,4-benzodioxin-6-yl)-4-fluoro-benzene-sulfonamide.

In the title compound, C(14)H(12)FNO(4)S, the dihedral angle between the aromatic rings is 50.26 (9)° and the C-S-N-C bond adopts a gauche conformation [torsion angle = -68.12 (15)°]. The dihydro-dioxine ring is disordered over two orientations, which both approximate to half-chairs, in a 0.880 (7):0.120 (7) ratio. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into C(4) chains propagating in [100]. Weak C-H⋯O and C-H⋯F inter-actions consolidate the packing.

Related literature

For related structures, see: Khan et al. (2011 ▶); Gelbrich et al. (2007 ▶).

Experimental

Crystal data

C14H12FNO4S

M = 309.31

Monoclinic,

a = 5.1542 (5) Å

b = 22.237 (3) Å

c = 12.0706 (13) Å

β = 94.422 (3)°

V = 1379.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.39 × 0.34 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer

11762 measured reflections

3156 independent reflections

2336 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.101

S = 1.02

3156 reflections

202 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812030863/bt5970sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030863/bt5970Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030863/bt5970Isup3.cml

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

C14H12FNO4S	F(000) = 640
Mr = 309.31	Dx = 1.489 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.1542 (5) Å	Cell parameters from 1453 reflections
b = 22.237 (3) Å	θ = 2.5–25.5°
c = 12.0706 (13) Å	µ = 0.26 mm−1
β = 94.422 (3)°	T = 296 K
V = 1379.3 (3) Å3	Prism, colourless
Z = 4	0.39 × 0.34 × 0.23 mm

Bruker APEXII CCD diffractometer	2336 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 27.5°, θmin = 1.8°
ω scans	h = −6→5
11762 measured reflections	k = −28→28
3156 independent reflections	l = −15→14

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0451P)2 + 0.3224P] where P = (Fo2 + 2Fc2)/3
3156 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.32 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	0.5881 (3)	0.25665 (7)	0.60034 (14)	0.0404 (4)
C2	0.7189 (4)	0.23608 (9)	0.51210 (17)	0.0565 (5)
H2	0.8515	0.2590	0.4852	0.068*
C3	0.6514 (5)	0.18133 (10)	0.46402 (18)	0.0664 (6)
H3	0.7375	0.1668	0.4046	0.080*
C4	0.4572 (4)	0.14930 (9)	0.50536 (17)	0.0564 (5)
C5	0.3224 (4)	0.16869 (8)	0.59056 (17)	0.0543 (5)
H5	0.1876	0.1458	0.6154	0.065*
C6	0.3891 (4)	0.22311 (8)	0.63959 (15)	0.0482 (4)
H6	0.3006	0.2371	0.6987	0.058*
F1	0.3949 (3)	0.09489 (6)	0.45976 (12)	0.0886 (4)
C7	0.4989 (3)	0.39470 (7)	0.48965 (15)	0.0429 (4)
C8	0.6750 (3)	0.43897 (7)	0.46691 (15)	0.0434 (4)
H8	0.7859	0.4549	0.5239	0.052*
C9	0.6860 (3)	0.45950 (7)	0.35926 (14)	0.0415 (4)
C10	0.5168 (3)	0.43651 (8)	0.27495 (15)	0.0457 (4)
C11	0.3469 (4)	0.39124 (9)	0.29867 (18)	0.0613 (5)
H11	0.2378	0.3746	0.2417	0.074*
C12	0.3366 (4)	0.37037 (9)	0.40506 (18)	0.0583 (5)
H12	0.2208	0.3399	0.4202	0.070*
C13	0.8923 (7)	0.51508 (15)	0.2265 (2)	0.0598 (8)	0.880 (7)
H13A	1.0029	0.4842	0.1985	0.072*	0.880 (7)
H13B	0.9770	0.5536	0.2185	0.072*	0.880 (7)
C13A	0.794 (6)	0.5341 (11)	0.2265 (19)	0.064 (7)*	0.120 (7)
H13C	0.6299	0.5555	0.2269	0.076*	0.120 (7)
H13D	0.9283	0.5628	0.2111	0.076*	0.120 (7)
C14	0.6350 (6)	0.51509 (11)	0.1600 (2)	0.0578 (9)	0.880 (7)
H14A	0.5239	0.5459	0.1879	0.069*	0.880 (7)
H14B	0.6601	0.5241	0.0830	0.069*	0.880 (7)
C14A	0.775 (4)	0.4882 (9)	0.1419 (15)	0.058 (6)*	0.120 (7)
H14C	0.9199	0.4603	0.1504	0.070*	0.120 (7)
H14D	0.7654	0.5054	0.0679	0.070*	0.120 (7)
S1	0.66702 (8)	0.32659 (2)	0.66316 (4)	0.04491 (14)
N1	0.4773 (3)	0.37724 (7)	0.60361 (14)	0.0490 (4)
H1	0.330 (4)	0.3731 (9)	0.6218 (16)	0.059*
O1	0.5996 (3)	0.32377 (7)	0.77539 (11)	0.0620 (4)
O2	0.9274 (2)	0.34095 (6)	0.63905 (12)	0.0603 (4)
O3	0.8603 (2)	0.50425 (6)	0.34055 (10)	0.0564 (4)
O4	0.5128 (3)	0.45743 (6)	0.16736 (11)	0.0586 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0334 (9)	0.0456 (9)	0.0420 (9)	0.0026 (7)	0.0025 (7)	0.0036 (7)
C2	0.0493 (12)	0.0695 (12)	0.0524 (11)	−0.0057 (9)	0.0153 (9)	−0.0025 (9)
C3	0.0714 (15)	0.0770 (14)	0.0526 (12)	0.0018 (11)	0.0160 (10)	−0.0162 (10)
C4	0.0634 (14)	0.0503 (10)	0.0537 (12)	0.0027 (9)	−0.0074 (10)	−0.0055 (9)
C5	0.0500 (12)	0.0474 (10)	0.0659 (13)	−0.0054 (8)	0.0062 (9)	0.0070 (9)
C6	0.0437 (11)	0.0485 (9)	0.0536 (11)	0.0015 (8)	0.0120 (8)	0.0043 (8)
F1	0.1154 (12)	0.0617 (8)	0.0870 (10)	−0.0070 (7)	−0.0023 (8)	−0.0230 (7)
C7	0.0333 (9)	0.0413 (8)	0.0543 (11)	0.0025 (7)	0.0050 (7)	−0.0014 (7)
C8	0.0368 (9)	0.0424 (9)	0.0500 (10)	−0.0032 (7)	−0.0025 (7)	−0.0069 (7)
C9	0.0337 (9)	0.0372 (8)	0.0530 (10)	−0.0017 (6)	0.0007 (7)	−0.0061 (7)
C10	0.0435 (10)	0.0427 (9)	0.0500 (11)	0.0015 (7)	−0.0034 (8)	−0.0053 (7)
C11	0.0547 (13)	0.0606 (12)	0.0653 (13)	−0.0182 (9)	−0.0154 (10)	−0.0056 (10)
C12	0.0457 (11)	0.0553 (11)	0.0725 (14)	−0.0174 (9)	−0.0049 (9)	0.0033 (10)
C13	0.0550 (18)	0.0660 (17)	0.0580 (16)	−0.0102 (14)	0.0026 (12)	0.0107 (12)
C14	0.0650 (19)	0.0518 (13)	0.0555 (15)	−0.0002 (11)	−0.0029 (12)	0.0041 (10)
S1	0.0329 (2)	0.0524 (3)	0.0494 (3)	−0.00419 (18)	0.00263 (17)	−0.00209 (19)
N1	0.0342 (8)	0.0510 (8)	0.0630 (10)	0.0015 (7)	0.0122 (7)	0.0001 (7)
O1	0.0648 (9)	0.0763 (9)	0.0449 (8)	−0.0063 (7)	0.0039 (6)	−0.0058 (6)
O2	0.0297 (7)	0.0679 (9)	0.0833 (10)	−0.0074 (6)	0.0038 (6)	−0.0003 (7)
O3	0.0567 (9)	0.0584 (8)	0.0529 (8)	−0.0218 (6)	−0.0032 (6)	0.0030 (6)
O4	0.0665 (9)	0.0568 (8)	0.0505 (8)	−0.0093 (6)	−0.0090 (6)	−0.0024 (6)

C1—C6	1.381 (2)	C11—C12	1.370 (3)
C1—C2	1.381 (2)	C11—H11	0.9300
C1—S1	1.7640 (17)	C12—H12	0.9300
C2—C3	1.382 (3)	C13—O3	1.419 (3)
C2—H2	0.9300	C13—C14	1.496 (4)
C3—C4	1.355 (3)	C13—H13A	0.9700
C3—H3	0.9300	C13—H13B	0.9700
C4—C5	1.355 (3)	C13A—C14A	1.44 (3)
C4—F1	1.357 (2)	C13A—O3	1.54 (2)
C5—C6	1.379 (3)	C13A—H13C	0.9700
C5—H5	0.9300	C13A—H13D	0.9700
C6—H6	0.9300	C14—O4	1.434 (3)
C7—C12	1.379 (2)	C14—H14A	0.9700
C7—C8	1.381 (2)	C14—H14B	0.9700
C7—N1	1.442 (2)	C14A—O4	1.566 (18)
C8—C9	1.383 (2)	C14A—H14C	0.9700
C8—H8	0.9300	C14A—H14D	0.9700
C9—O3	1.371 (2)	S1—O1	1.4256 (14)
C9—C10	1.386 (2)	S1—O2	1.4312 (13)
C10—O4	1.378 (2)	S1—N1	1.6228 (16)
C10—C11	1.379 (3)	N1—H1	0.81 (2)
C6—C1—C2	120.33 (17)	O3—C13—H13A	109.5
C6—C1—S1	118.77 (13)	C14—C13—H13A	109.5
C2—C1—S1	120.88 (14)	O3—C13—H13B	109.5
C1—C2—C3	119.58 (19)	C14—C13—H13B	109.5
C1—C2—H2	120.2	H13A—C13—H13B	108.1
C3—C2—H2	120.2	C14A—C13A—O3	109.0 (18)
C4—C3—C2	118.54 (19)	C14A—C13A—H13C	109.9
C4—C3—H3	120.7	O3—C13A—H13C	109.9
C2—C3—H3	120.7	C14A—C13A—H13D	109.9
C3—C4—C5	123.30 (19)	O3—C13A—H13D	109.9
C3—C4—F1	118.53 (19)	H13C—C13A—H13D	108.3
C5—C4—F1	118.17 (19)	O4—C14—C13	110.0 (2)
C4—C5—C6	118.64 (18)	O4—C14—H14A	109.7
C4—C5—H5	120.7	C13—C14—H14A	109.7
C6—C5—H5	120.7	O4—C14—H14B	109.7
C5—C6—C1	119.59 (17)	C13—C14—H14B	109.7
C5—C6—H6	120.2	H14A—C14—H14B	108.2
C1—C6—H6	120.2	C13A—C14A—O4	100.5 (18)
C12—C7—C8	120.18 (17)	C13A—C14A—H14C	111.7
C12—C7—N1	120.90 (16)	O4—C14A—H14C	111.7
C8—C7—N1	118.81 (16)	C13A—C14A—H14D	111.7
C7—C8—C9	119.83 (16)	O4—C14A—H14D	111.7
C7—C8—H8	120.1	H14C—C14A—H14D	109.4
C9—C8—H8	120.1	O1—S1—O2	120.26 (9)
O3—C9—C8	117.99 (14)	O1—S1—N1	105.59 (9)
O3—C9—C10	122.01 (16)	O2—S1—N1	107.32 (9)
C8—C9—C10	119.95 (16)	O1—S1—C1	107.74 (8)
O4—C10—C11	118.58 (16)	O2—S1—C1	107.34 (8)
O4—C10—C9	122.02 (16)	N1—S1—C1	108.09 (8)
C11—C10—C9	119.39 (17)	C7—N1—S1	121.42 (12)
C12—C11—C10	120.85 (17)	C7—N1—H1	115.5 (14)
C12—C11—H11	119.6	S1—N1—H1	110.2 (15)
C10—C11—H11	119.6	C9—O3—C13	114.18 (15)
C11—C12—C7	119.74 (17)	C9—O3—C13A	110.9 (10)
C11—C12—H12	120.1	C10—O4—C14	112.66 (14)
C7—C12—H12	120.1	C10—O4—C14A	112.4 (7)
O3—C13—C14	110.8 (2)
C6—C1—C2—C3	−0.8 (3)	C2—C1—S1—O1	−153.38 (16)
S1—C1—C2—C3	−179.50 (16)	C6—C1—S1—O2	158.72 (14)
C1—C2—C3—C4	0.0 (3)	C2—C1—S1—O2	−22.52 (18)
C2—C3—C4—C5	1.1 (3)	C6—C1—S1—N1	−85.80 (15)
C2—C3—C4—F1	−178.54 (19)	C2—C1—S1—N1	92.95 (16)
C3—C4—C5—C6	−1.5 (3)	C12—C7—N1—S1	97.69 (19)
F1—C4—C5—C6	178.17 (17)	C8—C7—N1—S1	−86.06 (19)
C4—C5—C6—C1	0.7 (3)	O1—S1—N1—C7	176.79 (14)
C2—C1—C6—C5	0.4 (3)	O2—S1—N1—C7	47.37 (16)
S1—C1—C6—C5	179.15 (14)	C1—S1—N1—C7	−68.12 (15)
C12—C7—C8—C9	0.9 (3)	C8—C9—O3—C13	169.3 (2)
N1—C7—C8—C9	−175.37 (15)	C10—C9—O3—C13	−13.3 (3)
C7—C8—C9—O3	178.83 (15)	C8—C9—O3—C13A	−163.5 (11)
C7—C8—C9—C10	1.3 (3)	C10—C9—O3—C13A	13.9 (11)
O3—C9—C10—O4	−0.3 (3)	C14—C13—O3—C9	43.1 (3)
C8—C9—C10—O4	177.12 (15)	C14—C13—O3—C13A	−45 (2)
O3—C9—C10—C11	179.60 (17)	C14A—C13A—O3—C9	−54 (2)
C8—C9—C10—C11	−3.0 (3)	C14A—C13A—O3—C13	48.9 (19)
O4—C10—C11—C12	−177.64 (18)	C11—C10—O4—C14	161.9 (2)
C9—C10—C11—C12	2.5 (3)	C9—C10—O4—C14	−18.2 (3)
C10—C11—C12—C7	−0.3 (3)	C11—C10—O4—C14A	−157.3 (9)
C8—C7—C12—C11	−1.5 (3)	C9—C10—O4—C14A	22.6 (9)
N1—C7—C12—C11	174.74 (18)	C13—C14—O4—C10	47.5 (3)
O3—C13—C14—O4	−61.6 (4)	C13—C14—O4—C14A	−50.3 (11)
O3—C13A—C14A—O4	72 (2)	C13A—C14A—O4—C10	−57.2 (18)
C6—C1—S1—O1	27.86 (16)	C13A—C14A—O4—C14	41.3 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.81 (2)	2.22 (2)	3.009 (2)	164 (2)
C3—H3···O1ii	0.93	2.53	3.368 (3)	150
C5—H5···O4iii	0.93	2.56	3.391 (2)	149
C8—H8···O3iv	0.93	2.52	3.446 (2)	172
C13—H13B···F1v	0.97	2.48	3.129 (3)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.81 (2)	2.22 (2)	3.009 (2)	164 (2)
C3—H3⋯O1ii	0.93	2.53	3.368 (3)	150
C5—H5⋯O4iii	0.93	2.56	3.391 (2)	149
C8—H8⋯O3iv	0.93	2.52	3.446 (2)	172
C13—H13B⋯F1v	0.97	2.48	3.129 (3)	125

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