N-(3,4-Difluoro-phen-yl)-3,4-dimethoxy-benzene-sulfonamide.

In the title sulfonamide derivative, C(14)H(13)F(2)NO(4)S, the dihedral angle between the benzene rings is 66.05 (9)°. The crystal structure is stabilized by weak inter-molecular N-H⋯O hydrogen bonds involving the amine and meth-oxy groups, which link the mol-ecules into a one-dimensional chain. No significant inter-chain contacts are observed.

Related literature

For general background on skin-whitening agents, see: Dawley & Flurkey (1993 ▶); Nerya et al. (2003 ▶); Juana et al. (1994 ▶); Briganti et al. (2003 ▶). For the synthesis, see: Hussain et al. (2003 ▶).

Experimental

Crystal data

C14H13F2NO4S

M = 329.31

Monoclinic,

a = 12.2886 (10) Å

b = 8.5662 (7) Å

c = 14.5546 (12) Å

β = 109.655 (2)°

V = 1442.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 295 (2) K

0.25 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.928, T max = 0.957

9690 measured reflections

3308 independent reflections

1700 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.126

S = 0.99

3308 reflections

204 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012610/bh2170sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012610/bh2170Isup2.hkl

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

C14H13F2NO4S	F000 = 680
Mr = 329.31	Dx = 1.516 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1598 reflections
a = 12.2886 (10) Å	θ = 2.8–23.5º
b = 8.5662 (7) Å	µ = 0.26 mm−1
c = 14.5546 (12) Å	T = 295 (2) K
β = 109.655 (2)º	Block, colourless
V = 1442.8 (2) Å3	0.25 × 0.18 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	Rint = 0.042
φ and ω scans	θmax = 27.5º
Absorption correction: multi-scan(SADABS; Bruker, 2002)	θmin = 1.8º
Tmin = 0.928, Tmax = 0.957	h = −15→14
9690 measured reflections	k = −11→9
3308 independent reflections	l = −18→18
1700 reflections with I > 2σ(I)

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0426P)2 + 0.5561P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.044	(Δ/σ)max = 0.001
wR(F2) = 0.126	Δρmax = 0.19 e Å−3
S = 0.99	Δρmin = −0.21 e Å−3
3308 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
204 parameters	Extinction coefficient: 0.0349 (19)

	x	y	z	Uiso*/Ueq
F1	0.37106 (16)	0.1400 (3)	−0.04021 (13)	0.0975 (7)
F2	0.3788 (2)	0.0318 (3)	0.13264 (17)	0.1271 (9)
C1	0.6212 (2)	0.3457 (3)	0.11332 (19)	0.0492 (7)
C2	0.5338 (2)	0.2966 (3)	0.0306 (2)	0.0584 (8)
H2	0.5288	0.3352	−0.0304	0.07*
C3	0.4554 (2)	0.1914 (4)	0.0395 (2)	0.0609 (8)
C4	0.4593 (3)	0.1366 (4)	0.1281 (2)	0.0753 (10)
C5	0.5430 (3)	0.1849 (5)	0.2102 (2)	0.0885 (12)
H5	0.5454	0.1475	0.2708	0.106*
C6	0.6248 (2)	0.2906 (4)	0.2030 (2)	0.0692 (9)
H6	0.6826	0.3245	0.2591	0.083*
N7	0.7042 (2)	0.4591 (3)	0.1068 (2)	0.0595 (7)
H7	0.738 (2)	0.489 (4)	0.158 (2)	0.062 (10)*
S8	0.78080 (6)	0.43912 (9)	0.03547 (5)	0.0595 (3)
O9	0.84833 (17)	0.5777 (2)	0.04834 (17)	0.0802 (7)
O10	0.70295 (15)	0.3991 (3)	−0.05866 (13)	0.0709 (6)
C11	0.8750 (2)	0.2809 (3)	0.07756 (18)	0.0490 (7)
C12	0.9910 (2)	0.3073 (3)	0.13211 (17)	0.0478 (6)
H12	1.0184	0.4087	0.1468	0.057*
C13	1.0644 (2)	0.1829 (3)	0.16380 (17)	0.0472 (6)
C14	1.0231 (2)	0.0296 (3)	0.14189 (18)	0.0480 (6)
C15	0.9086 (2)	0.0050 (3)	0.0875 (2)	0.0559 (7)
H15	0.8809	−0.0962	0.0724	0.067*
C16	0.8350 (2)	0.1300 (3)	0.0554 (2)	0.0566 (7)
H16	0.7579	0.1128	0.0187	0.068*
O17	1.17904 (15)	0.1936 (2)	0.21844 (13)	0.0614 (5)
C18	1.2333 (2)	0.3419 (4)	0.2277 (2)	0.0669 (9)
H18A	1.3129	0.3326	0.2681	0.1*
H18B	1.1949	0.4141	0.2569	0.1*
H18C	1.2288	0.3792	0.1643	0.1*
O19	1.10296 (15)	−0.0832 (2)	0.17753 (14)	0.0599 (5)
C20	1.0682 (3)	−0.2409 (3)	0.1507 (2)	0.0668 (8)
H20A	1.132	−0.3098	0.1805	0.1*
H20B	1.0441	−0.2514	0.0811	0.1*
H20C	1.005	−0.2674	0.1727	0.1*

	U11	U22	U33	U12	U13	U23
F1	0.0780 (12)	0.1205 (18)	0.0749 (12)	−0.0470 (12)	0.0005 (10)	−0.0069 (11)
F2	0.1139 (17)	0.160 (2)	0.1037 (16)	−0.0684 (17)	0.0321 (14)	0.0185 (15)
C1	0.0374 (13)	0.0490 (16)	0.0540 (17)	0.0026 (12)	0.0060 (12)	−0.0074 (13)
C2	0.0499 (16)	0.0634 (19)	0.0522 (17)	−0.0065 (14)	0.0044 (13)	0.0047 (14)
C3	0.0480 (16)	0.069 (2)	0.0555 (18)	−0.0104 (15)	0.0037 (14)	−0.0058 (15)
C4	0.0615 (19)	0.088 (3)	0.075 (2)	−0.0210 (18)	0.0223 (17)	0.0036 (19)
C5	0.074 (2)	0.134 (4)	0.057 (2)	−0.015 (2)	0.0207 (18)	0.008 (2)
C6	0.0520 (17)	0.096 (3)	0.0530 (19)	−0.0028 (17)	0.0093 (14)	−0.0121 (17)
N7	0.0462 (13)	0.0581 (16)	0.0618 (17)	−0.0029 (12)	0.0019 (12)	−0.0102 (13)
S8	0.0460 (4)	0.0573 (5)	0.0647 (5)	−0.0070 (4)	0.0048 (3)	0.0101 (4)
O9	0.0582 (12)	0.0579 (14)	0.1098 (18)	−0.0137 (10)	0.0090 (12)	0.0198 (12)
O10	0.0543 (11)	0.0896 (17)	0.0556 (12)	−0.0054 (10)	0.0009 (9)	0.0153 (11)
C11	0.0422 (14)	0.0530 (17)	0.0480 (15)	−0.0059 (13)	0.0102 (12)	0.0031 (13)
C12	0.0480 (14)	0.0453 (16)	0.0459 (15)	−0.0115 (12)	0.0102 (12)	−0.0005 (12)
C13	0.0420 (14)	0.0526 (17)	0.0427 (14)	−0.0059 (13)	0.0084 (11)	0.0005 (12)
C14	0.0469 (14)	0.0473 (17)	0.0482 (15)	−0.0036 (13)	0.0138 (12)	0.0015 (12)
C15	0.0509 (16)	0.0509 (17)	0.0643 (18)	−0.0130 (14)	0.0171 (14)	−0.0060 (14)
C16	0.0418 (14)	0.062 (2)	0.0598 (18)	−0.0137 (14)	0.0092 (13)	−0.0027 (15)
O17	0.0470 (10)	0.0523 (12)	0.0707 (13)	−0.0082 (9)	0.0010 (9)	0.0051 (10)
C18	0.0486 (16)	0.061 (2)	0.078 (2)	−0.0199 (14)	0.0042 (14)	0.0031 (16)
O19	0.0563 (11)	0.0441 (12)	0.0732 (13)	−0.0037 (9)	0.0138 (10)	−0.0016 (9)
C20	0.0727 (19)	0.0473 (18)	0.081 (2)	−0.0054 (16)	0.0270 (17)	−0.0061 (16)

F1—C3	1.343 (3)	C11—C12	1.398 (3)
F2—C4	1.354 (3)	C12—C13	1.372 (4)
C1—C6	1.375 (4)	C12—H12	0.93
C1—C2	1.382 (3)	C13—O17	1.369 (3)
C1—N7	1.434 (4)	C13—C14	1.405 (4)
C2—C3	1.357 (4)	C14—O19	1.350 (3)
C2—H2	0.93	C14—C15	1.379 (3)
C3—C4	1.359 (4)	C15—C16	1.378 (4)
C4—C5	1.352 (4)	C15—H15	0.93
C5—C6	1.383 (4)	C16—H16	0.93
C5—H5	0.93	O17—C18	1.420 (3)
C6—H6	0.93	C18—H18A	0.96
N7—S8	1.628 (3)	C18—H18B	0.96
N7—H7	0.76 (3)	C18—H18C	0.96
S8—O10	1.424 (2)	O19—C20	1.431 (3)
S8—O9	1.424 (2)	C20—H20A	0.96
S8—C11	1.754 (3)	C20—H20B	0.96
C11—C16	1.381 (4)	C20—H20C	0.96
C6—C1—C2	119.3 (3)	C13—C12—C11	119.6 (2)
C6—C1—N7	119.9 (2)	C13—C12—H12	120.2
C2—C1—N7	120.7 (3)	C11—C12—H12	120.2
C3—C2—C1	119.2 (3)	O17—C13—C12	125.1 (2)
C3—C2—H2	120.4	O17—C13—C14	114.6 (2)
C1—C2—H2	120.4	C12—C13—C14	120.3 (2)
F1—C3—C2	120.1 (3)	O19—C14—C15	125.5 (2)
F1—C3—C4	118.5 (3)	O19—C14—C13	114.9 (2)
C2—C3—C4	121.4 (3)	C15—C14—C13	119.6 (3)
C5—C4—F2	120.7 (3)	C16—C15—C14	120.1 (3)
C5—C4—C3	120.4 (3)	C16—C15—H15	119.9
F2—C4—C3	118.9 (3)	C14—C15—H15	119.9
C4—C5—C6	119.3 (3)	C15—C16—C11	120.5 (2)
C4—C5—H5	120.3	C15—C16—H16	119.8
C6—C5—H5	120.3	C11—C16—H16	119.8
C1—C6—C5	120.3 (3)	C13—O17—C18	118.3 (2)
C1—C6—H6	119.8	O17—C18—H18A	109.5
C5—C6—H6	119.8	O17—C18—H18B	109.5
C1—N7—S8	123.2 (2)	H18A—C18—H18B	109.5
C1—N7—H7	109 (2)	O17—C18—H18C	109.5
S8—N7—H7	115 (2)	H18A—C18—H18C	109.5
O10—S8—O9	120.03 (13)	H18B—C18—H18C	109.5
O10—S8—N7	107.04 (13)	C14—O19—C20	117.3 (2)
O9—S8—N7	105.36 (14)	O19—C20—H20A	109.5
O10—S8—C11	107.51 (13)	O19—C20—H20B	109.5
O9—S8—C11	108.15 (12)	H20A—C20—H20B	109.5
N7—S8—C11	108.29 (13)	O19—C20—H20C	109.5
C16—C11—C12	119.9 (2)	H20A—C20—H20C	109.5
C16—C11—S8	120.0 (2)	H20B—C20—H20C	109.5
C12—C11—S8	120.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O17i	0.76 (3)	2.48 (3)	3.180 (3)	155 (3)
N7—H7···O19i	0.76 (3)	2.61 (3)	3.256 (3)	144 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O17i	0.76 (3)	2.48 (3)	3.180 (3)	155 (3)
N7—H7⋯O19i	0.76 (3)	2.61 (3)	3.256 (3)	144 (3)

Symmetry code: (i) .