N-(2,3-Dimethyl-phen-yl)-4-fluoro-N-[(4-fluoro-phen-yl)sulfon-yl]benzene-sulfonamide.

In the title compound, C(20)H(17)F(2)NO(4)S(2), the dihedral angles between the o-xylene ring and the fluoro-benzene rings are 31.7 (1) and 32.8 (1)°, and the dihedral angle between the fluoro-benzene rings is 50.9 (1)°. The C-N-S-C torsion angles are 76.7 (2) and 101.8 (2)°. In the crystal, mol-ecules are connected by C-H⋯O inter-actions into sheets in the ab plane.

Related literature

For related crystal structures, see: Hanson & Hitchcock (2004 ▶); Low et al. (2006 ▶); Mughal et al. (2012 ▶).

Experimental

Crystal data

C20H17F2NO4S2

M = 437.47

Orthorhombic,

a = 9.9493 (5) Å

b = 14.7107 (8) Å

c = 26.6871 (17) Å

V = 3906.0 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.32 mm−1

T = 296 K

0.28 × 0.25 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.916, T max = 0.930

31734 measured reflections

4352 independent reflections

2943 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.133

S = 1.02

4352 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAIn class="Chemical">NT (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/S1600536812039402/ld2072sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039402/ld2072Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039402/ld2072Isup3.cml

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

C20H17F2NO4S2	Dx = 1.488 Mg m−3
Mr = 437.47	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 202 reflections
a = 9.9493 (5) Å	θ = 3.2–20.5°
b = 14.7107 (8) Å	µ = 0.32 mm−1
c = 26.6871 (17) Å	T = 296 K
V = 3906.0 (4) Å3	Block, yellow
Z = 8	0.28 × 0.25 × 0.23 mm
F(000) = 1808

Bruker APEXII CCD diffractometer	4352 independent reflections
Radiation source: fine-focus sealed tube	2943 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
ω scans	θmax = 27.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −12→12
Tmin = 0.916, Tmax = 0.930	k = −18→14
31734 measured reflections	l = −34→34

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0524P)2 + 2.7378P] where P = (Fo2 + 2Fc2)/3
4352 reflections	(Δ/σ)max < 0.001
264 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.29 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
C1	0.6678 (3)	0.45285 (18)	0.13773 (11)	0.0504 (7)
C2	0.7555 (3)	0.48512 (18)	0.10252 (10)	0.0540 (7)
C3	0.8910 (3)	0.4952 (2)	0.11660 (13)	0.0616 (8)
C4	0.9311 (4)	0.4696 (2)	0.16383 (14)	0.0717 (9)
H4	1.0208	0.4763	0.1729	0.086*
C5	0.8414 (4)	0.4343 (2)	0.19804 (14)	0.0765 (10)
H5	0.8715	0.4167	0.2296	0.092*
C6	0.7092 (3)	0.4250 (2)	0.18605 (11)	0.0595 (8)
H6	0.6480	0.4011	0.2089	0.071*
C7	0.7112 (3)	0.5083 (2)	0.05128 (11)	0.0666 (9)
H7A	0.7561	0.4696	0.0276	0.100*
H7B	0.7328	0.5706	0.0443	0.100*
H7C	0.6158	0.4996	0.0486	0.100*
C8	0.9920 (4)	0.5330 (3)	0.08077 (16)	0.0961 (13)
H8A	1.0796	0.5312	0.0958	0.144*
H8B	0.9691	0.5947	0.0729	0.144*
H8C	0.9922	0.4973	0.0506	0.144*
C9	0.4640 (3)	0.62628 (17)	0.11107 (10)	0.0451 (6)
C10	0.5733 (3)	0.68129 (19)	0.12047 (12)	0.0571 (7)
H10	0.6275	0.6707	0.1483	0.069*
C11	0.6018 (4)	0.7518 (2)	0.08853 (14)	0.0733 (9)
H11	0.6744	0.7902	0.0943	0.088*
C12	0.5205 (4)	0.7638 (2)	0.04815 (14)	0.0768 (10)
C13	0.4101 (4)	0.7119 (2)	0.03854 (12)	0.0749 (10)
H13	0.3554	0.7241	0.0111	0.090*
C14	0.3816 (3)	0.6414 (2)	0.07036 (10)	0.0583 (7)
H14	0.3077	0.6041	0.0646	0.070*
C15	0.3779 (3)	0.29685 (18)	0.14708 (9)	0.0449 (6)
C16	0.2445 (3)	0.31051 (19)	0.15903 (10)	0.0517 (7)
H16	0.1919	0.3501	0.1402	0.062*
C17	0.1902 (3)	0.2645 (2)	0.19928 (11)	0.0557 (7)
H17	0.1007	0.2728	0.2083	0.067*
C18	0.2703 (3)	0.2067 (2)	0.22544 (10)	0.0542 (7)
C19	0.4012 (3)	0.1897 (2)	0.21330 (11)	0.0569 (7)
H19	0.4518	0.1480	0.2314	0.068*
C20	0.4558 (3)	0.23611 (19)	0.17354 (10)	0.0518 (7)
H20	0.5450	0.2265	0.1645	0.062*
S1	0.43137 (7)	0.53555 (5)	0.15106 (3)	0.0483 (2)
S2	0.45376 (7)	0.35921 (5)	0.09885 (2)	0.0494 (2)
F1	0.5499 (3)	0.83173 (15)	0.01607 (9)	0.1272 (10)
F2	0.21844 (19)	0.16374 (13)	0.26576 (7)	0.0773 (6)
O1	0.4877 (2)	0.55627 (14)	0.19840 (7)	0.0654 (6)
O2	0.29538 (19)	0.50962 (14)	0.14719 (9)	0.0677 (6)
O3	0.3540 (2)	0.39068 (16)	0.06534 (7)	0.0704 (6)
O4	0.5668 (2)	0.30948 (14)	0.08134 (7)	0.0622 (5)
N1	0.5226 (2)	0.44974 (14)	0.12742 (8)	0.0444 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0518 (16)	0.0389 (14)	0.0604 (17)	−0.0005 (12)	0.0075 (13)	−0.0049 (12)
C2	0.0611 (17)	0.0435 (16)	0.0574 (17)	0.0019 (13)	0.0051 (14)	−0.0018 (13)
C3	0.0486 (16)	0.0509 (17)	0.085 (2)	0.0025 (14)	−0.0022 (16)	−0.0086 (16)
C4	0.064 (2)	0.063 (2)	0.088 (2)	−0.0010 (17)	0.0044 (19)	−0.0038 (18)
C5	0.081 (2)	0.080 (2)	0.068 (2)	0.006 (2)	−0.0230 (19)	0.0015 (18)
C6	0.0580 (18)	0.0585 (18)	0.0619 (18)	−0.0002 (15)	−0.0060 (14)	0.0022 (14)
C7	0.083 (2)	0.0597 (19)	0.0573 (18)	0.0066 (17)	0.0038 (16)	0.0049 (15)
C8	0.071 (2)	0.105 (3)	0.112 (3)	−0.021 (2)	0.015 (2)	0.003 (3)
C9	0.0491 (15)	0.0359 (13)	0.0502 (14)	−0.0006 (12)	0.0011 (12)	−0.0053 (11)
C10	0.0583 (18)	0.0478 (16)	0.0653 (18)	−0.0045 (14)	−0.0030 (15)	−0.0058 (14)
C11	0.082 (2)	0.0494 (18)	0.089 (3)	−0.0206 (17)	0.008 (2)	−0.0050 (17)
C12	0.115 (3)	0.0473 (18)	0.068 (2)	−0.007 (2)	0.017 (2)	0.0057 (16)
C13	0.109 (3)	0.068 (2)	0.0487 (17)	0.008 (2)	−0.0091 (18)	0.0019 (16)
C14	0.0642 (18)	0.0571 (18)	0.0534 (17)	−0.0027 (15)	−0.0054 (14)	−0.0081 (14)
C15	0.0503 (15)	0.0404 (14)	0.0440 (14)	−0.0087 (12)	−0.0049 (12)	−0.0045 (11)
C16	0.0473 (15)	0.0484 (16)	0.0594 (17)	−0.0078 (13)	−0.0102 (13)	0.0035 (13)
C17	0.0451 (15)	0.0568 (17)	0.0651 (18)	−0.0104 (14)	0.0022 (14)	−0.0016 (14)
C18	0.0577 (18)	0.0554 (17)	0.0496 (15)	−0.0180 (14)	−0.0034 (13)	0.0017 (13)
C19	0.0578 (18)	0.0541 (17)	0.0588 (17)	−0.0048 (14)	−0.0106 (14)	0.0102 (14)
C20	0.0458 (15)	0.0510 (16)	0.0585 (17)	−0.0007 (13)	−0.0005 (13)	0.0005 (13)
S1	0.0486 (4)	0.0448 (4)	0.0516 (4)	0.0001 (3)	0.0086 (3)	−0.0025 (3)
S2	0.0592 (4)	0.0494 (4)	0.0397 (3)	−0.0057 (3)	−0.0004 (3)	−0.0028 (3)
F1	0.209 (3)	0.0732 (14)	0.0998 (17)	−0.0283 (17)	0.0147 (18)	0.0319 (13)
F2	0.0742 (12)	0.0903 (14)	0.0672 (11)	−0.0198 (10)	0.0045 (10)	0.0228 (10)
O1	0.0839 (15)	0.0678 (13)	0.0445 (11)	0.0104 (12)	0.0046 (10)	−0.0086 (9)
O2	0.0462 (11)	0.0566 (13)	0.1003 (17)	−0.0017 (10)	0.0155 (11)	0.0027 (11)
O3	0.0764 (15)	0.0838 (15)	0.0510 (11)	−0.0119 (12)	−0.0174 (11)	0.0096 (11)
O4	0.0746 (14)	0.0565 (12)	0.0556 (12)	−0.0007 (11)	0.0155 (10)	−0.0153 (10)
N1	0.0429 (11)	0.0399 (12)	0.0503 (12)	−0.0012 (9)	0.0031 (10)	−0.0043 (10)

C1—C2	1.367 (4)	C11—H11	0.9300
C1—C6	1.414 (4)	C12—F1	1.348 (4)
C1—N1	1.471 (4)	C12—C13	1.362 (5)
C2—C3	1.407 (4)	C13—C14	1.371 (4)
C2—C7	1.476 (4)	C13—H13	0.9300
C3—C4	1.375 (5)	C14—H14	0.9300
C3—C8	1.495 (5)	C15—C20	1.377 (4)
C4—C5	1.378 (5)	C15—C16	1.380 (4)
C4—H4	0.9300	C15—S2	1.751 (3)
C5—C6	1.361 (4)	C16—C17	1.380 (4)
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—C18	1.358 (4)
C7—H7A	0.9600	C17—H17	0.9300
C7—H7B	0.9600	C18—F2	1.350 (3)
C7—H7C	0.9600	C18—C19	1.365 (4)
C8—H8A	0.9600	C19—C20	1.374 (4)
C8—H8B	0.9600	C19—H19	0.9300
C8—H8C	0.9600	C20—H20	0.9300
C9—C10	1.378 (4)	S1—O2	1.410 (2)
C9—C14	1.379 (4)	S1—O1	1.415 (2)
C9—S1	1.739 (3)	S1—N1	1.678 (2)
C10—C11	1.373 (4)	S2—O3	1.414 (2)
C10—H10	0.9300	S2—O4	1.421 (2)
C11—C12	1.359 (5)	S2—N1	1.681 (2)
C2—C1—C6	122.8 (3)	C11—C12—C13	123.8 (3)
C2—C1—N1	120.6 (3)	C12—C13—C14	118.3 (3)
C6—C1—N1	116.6 (2)	C12—C13—H13	120.8
C1—C2—C3	117.6 (3)	C14—C13—H13	120.8
C1—C2—C7	121.8 (3)	C13—C14—C9	119.1 (3)
C3—C2—C7	120.6 (3)	C13—C14—H14	120.4
C4—C3—C2	119.6 (3)	C9—C14—H14	120.4
C4—C3—C8	119.5 (3)	C20—C15—C16	121.1 (3)
C2—C3—C8	120.8 (3)	C20—C15—S2	118.3 (2)
C3—C4—C5	121.5 (3)	C16—C15—S2	120.5 (2)
C3—C4—H4	119.3	C17—C16—C15	119.0 (3)
C5—C4—H4	119.3	C17—C16—H16	120.5
C6—C5—C4	120.6 (3)	C15—C16—H16	120.5
C6—C5—H5	119.7	C18—C17—C16	118.5 (3)
C4—C5—H5	119.7	C18—C17—H17	120.7
C5—C6—C1	117.8 (3)	C16—C17—H17	120.7
C5—C6—H6	121.1	F2—C18—C17	118.6 (3)
C1—C6—H6	121.1	F2—C18—C19	117.9 (3)
C2—C7—H7A	109.5	C17—C18—C19	123.5 (3)
C2—C7—H7B	109.5	C18—C19—C20	118.0 (3)
H7A—C7—H7B	109.5	C18—C19—H19	121.0
C2—C7—H7C	109.5	C20—C19—H19	121.0
H7A—C7—H7C	109.5	C19—C20—C15	119.7 (3)
H7B—C7—H7C	109.5	C19—C20—H20	120.1
C3—C8—H8A	109.5	C15—C20—H20	120.1
C3—C8—H8B	109.5	O2—S1—O1	120.26 (14)
H8A—C8—H8B	109.5	O2—S1—N1	106.76 (12)
C3—C8—H8C	109.5	O1—S1—N1	106.45 (12)
H8A—C8—H8C	109.5	O2—S1—C9	110.01 (13)
H8B—C8—H8C	109.5	O1—S1—C9	107.96 (13)
C10—C9—C14	121.2 (3)	N1—S1—C9	104.21 (11)
C10—C9—S1	119.1 (2)	O3—S2—O4	121.08 (13)
C14—C9—S1	119.7 (2)	O3—S2—N1	108.28 (13)
C11—C10—C9	119.6 (3)	O4—S2—N1	103.57 (11)
C11—C10—H10	120.2	O3—S2—C15	109.50 (13)
C9—C10—H10	120.2	O4—S2—C15	108.24 (13)
C12—C11—C10	117.9 (3)	N1—S2—C15	104.92 (11)
C12—C11—H11	121.0	C1—N1—S1	115.94 (17)
C10—C11—H11	121.0	C1—N1—S2	120.65 (17)
F1—C12—C11	118.1 (4)	S1—N1—S2	123.10 (13)
F1—C12—C13	118.1 (4)
C6—C1—C2—C3	−3.5 (4)	C18—C19—C20—C15	−0.7 (4)
N1—C1—C2—C3	173.5 (2)	C16—C15—C20—C19	−1.6 (4)
C6—C1—C2—C7	176.0 (3)	S2—C15—C20—C19	176.6 (2)
N1—C1—C2—C7	−6.9 (4)	C10—C9—S1—O2	158.3 (2)
C1—C2—C3—C4	2.3 (4)	C14—C9—S1—O2	−22.4 (3)
C7—C2—C3—C4	−177.3 (3)	C10—C9—S1—O1	25.3 (3)
C1—C2—C3—C8	−177.9 (3)	C14—C9—S1—O1	−155.4 (2)
C7—C2—C3—C8	2.5 (5)	C10—C9—S1—N1	−87.6 (2)
C2—C3—C4—C5	−0.2 (5)	C14—C9—S1—N1	91.7 (2)
C8—C3—C4—C5	−179.9 (3)	C20—C15—S2—O3	158.7 (2)
C3—C4—C5—C6	−0.9 (5)	C16—C15—S2—O3	−23.2 (3)
C4—C5—C6—C1	−0.2 (5)	C20—C15—S2—O4	24.8 (2)
C2—C1—C6—C5	2.5 (5)	C16—C15—S2—O4	−157.1 (2)
N1—C1—C6—C5	−174.6 (3)	C20—C15—S2—N1	−85.3 (2)
C14—C9—C10—C11	−0.7 (4)	C16—C15—S2—N1	92.8 (2)
S1—C9—C10—C11	178.6 (2)	C2—C1—N1—S1	−98.9 (3)
C9—C10—C11—C12	−0.8 (5)	C6—C1—N1—S1	78.3 (3)
C10—C11—C12—F1	−178.5 (3)	C2—C1—N1—S2	87.2 (3)
C10—C11—C12—C13	2.4 (6)	C6—C1—N1—S2	−95.6 (3)
F1—C12—C13—C14	178.4 (3)	O2—S1—N1—C1	−166.84 (19)
C11—C12—C13—C14	−2.5 (6)	O1—S1—N1—C1	−37.2 (2)
C12—C13—C14—C9	0.9 (5)	C9—S1—N1—C1	76.7 (2)
C10—C9—C14—C13	0.6 (4)	O2—S1—N1—S2	6.85 (19)
S1—C9—C14—C13	−178.6 (2)	O1—S1—N1—S2	136.46 (16)
C20—C15—C16—C17	2.2 (4)	C9—S1—N1—S2	−109.56 (16)
S2—C15—C16—C17	−175.9 (2)	O3—S2—N1—C1	−141.3 (2)
C15—C16—C17—C18	−0.5 (4)	O4—S2—N1—C1	−11.6 (2)
C16—C17—C18—F2	178.0 (2)	C15—S2—N1—C1	101.8 (2)
C16—C17—C18—C19	−1.8 (4)	O3—S2—N1—S1	45.28 (19)
F2—C18—C19—C20	−177.4 (2)	O4—S2—N1—S1	175.00 (15)
C17—C18—C19—C20	2.4 (4)	C15—S2—N1—S1	−71.57 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2i	0.96	2.57	3.517 (5)	170
C19—H19···O1ii	0.93	2.39	3.260 (4)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O2i	0.96	2.57	3.517 (5)	170
C19—H19⋯O1ii	0.93	2.39	3.260 (4)	157

Symmetry codes: (i) ; (ii) .