4-(4-Fluoro-benzene-sulfonamido)-phenyl 4-fluoro-benzene-sulfonate.

In the title compound, C(18)H(13)F(2)NO(5)S(2), the complete mol-ecule is generated by a crystallographic inversion centre, and the O atom and the N-H group attached to the central ring are statistically disordered. The dihedral angle between the central and terminal benzene rings is 64.03 (6)°. In the crystal, N-H⋯O, C-H⋯F and C-H⋯O inter-actions link the mol-ecules into a three-dimensional network.

Related literature

For a related structure showing similar statistical disorder of its O atom and NH group, see: Al Najjar et al. (2012 ▶). For background to the biological activity of benzene­sulfonates, see: Supuran et al. (2003 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H13F2NO5S2

M = 425.41

Monoclinic,

a = 8.9683 (1) Å

b = 11.0323 (1) Å

c = 9.3314 (1) Å

β = 102.363 (1)°

V = 901.85 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 100 K

0.37 × 0.33 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.883, T max = 0.930

12757 measured reflections

3235 independent reflections

2940 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.09

3235 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.39 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) I, global. DOI: 10.1107/S1600536812009877/hb6664sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009877/hb6664Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009877/hb6664Isup3.cml

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

C18H13F2NO5S2	F(000) = 436
Mr = 425.41	Dx = 1.567 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7746 reflections
a = 8.9683 (1) Å	θ = 2.3–32.6°
b = 11.0323 (1) Å	µ = 0.35 mm−1
c = 9.3314 (1) Å	T = 100 K
β = 102.363 (1)°	Block, yellow
V = 901.85 (2) Å3	0.37 × 0.33 × 0.21 mm
Z = 2

Bruker SMART APEXII CCD diffractometer	3235 independent reflections
Radiation source: fine-focus sealed tube	2940 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 32.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.883, Tmax = 0.930	k = −16→16
12757 measured reflections	l = −12→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0442P)2 + 0.4073P] where P = (Fo2 + 2Fc2)/3
3235 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.39 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 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)
S1	0.19643 (3)	0.57696 (3)	0.40553 (3)	0.02189 (8)
F1	0.48038 (14)	0.10387 (9)	0.39858 (12)	0.0534 (3)
O1	0.03218 (11)	0.56620 (9)	0.29564 (11)	0.0265 (2)	0.50
N1	0.03218 (11)	0.56620 (9)	0.29564 (11)	0.0265 (2)	0.50
H1N1	−0.0391	0.5177	0.3342	0.032*	0.50
O2	0.15869 (11)	0.59542 (9)	0.54583 (10)	0.02712 (18)
O3	0.28500 (11)	0.66585 (8)	0.34966 (11)	0.0302 (2)
C1	0.41366 (16)	0.21362 (12)	0.39786 (15)	0.0318 (3)
C2	0.29275 (15)	0.22427 (12)	0.46723 (16)	0.0311 (3)
H2A	0.2565	0.1562	0.5119	0.037*
C3	0.22599 (13)	0.33732 (11)	0.46964 (14)	0.0269 (2)
H3A	0.1428	0.3483	0.5166	0.032*
C4	0.28240 (12)	0.43473 (10)	0.40228 (12)	0.01905 (19)
C5	0.40364 (13)	0.42142 (11)	0.33233 (13)	0.0248 (2)
H5A	0.4402	0.4889	0.2868	0.030*
C6	0.47055 (16)	0.30807 (13)	0.32990 (15)	0.0323 (3)
H6A	0.5533	0.2962	0.2826	0.039*
C7	0.08657 (15)	0.60289 (12)	0.05220 (15)	0.0299 (3)
H7A	0.1450	0.6725	0.0882	0.036*
C8	0.02046 (14)	0.53190 (11)	0.14551 (13)	0.0258 (2)
C9	−0.06539 (15)	0.43016 (12)	0.09444 (15)	0.0300 (3)
H9A	−0.1097	0.3831	0.1597	0.036*

	U11	U22	U33	U12	U13	U23
S1	0.02541 (13)	0.01878 (14)	0.02456 (14)	0.00237 (9)	0.01219 (10)	0.00205 (9)
F1	0.0779 (7)	0.0299 (5)	0.0536 (6)	0.0271 (5)	0.0170 (5)	0.0026 (4)
O1	0.0272 (4)	0.0288 (5)	0.0277 (4)	0.0093 (3)	0.0154 (3)	0.0084 (4)
N1	0.0272 (4)	0.0288 (5)	0.0277 (4)	0.0093 (3)	0.0154 (3)	0.0084 (4)
O2	0.0327 (4)	0.0280 (4)	0.0236 (4)	0.0023 (3)	0.0127 (3)	−0.0018 (3)
O3	0.0369 (5)	0.0206 (4)	0.0376 (5)	−0.0023 (3)	0.0183 (4)	0.0035 (3)
C1	0.0406 (6)	0.0230 (6)	0.0289 (6)	0.0110 (5)	0.0008 (5)	−0.0027 (5)
C2	0.0334 (6)	0.0211 (5)	0.0364 (6)	−0.0012 (4)	0.0020 (5)	0.0050 (5)
C3	0.0237 (5)	0.0239 (5)	0.0336 (6)	0.0002 (4)	0.0073 (4)	0.0065 (5)
C4	0.0185 (4)	0.0189 (5)	0.0197 (4)	0.0005 (3)	0.0042 (3)	−0.0003 (4)
C5	0.0237 (5)	0.0267 (6)	0.0259 (5)	0.0030 (4)	0.0096 (4)	0.0008 (4)
C6	0.0342 (6)	0.0342 (7)	0.0306 (6)	0.0130 (5)	0.0113 (5)	−0.0003 (5)
C7	0.0329 (6)	0.0269 (6)	0.0349 (6)	0.0075 (5)	0.0179 (5)	0.0146 (5)
C8	0.0281 (5)	0.0255 (5)	0.0281 (5)	0.0116 (4)	0.0159 (4)	0.0120 (4)
C9	0.0313 (6)	0.0289 (6)	0.0351 (6)	0.0076 (4)	0.0188 (5)	0.0162 (5)

S1—O3	1.4289 (9)	C3—H3A	0.9500
S1—O2	1.4351 (9)	C4—C5	1.3905 (15)
S1—O1	1.6089 (11)	C5—C6	1.3893 (17)
S1—C4	1.7515 (11)	C5—H5A	0.9500
F1—C1	1.3499 (15)	C6—H6A	0.9500
O1—C8	1.4332 (16)	C7—C9i	1.389 (2)
O1—H1N1	0.9606	C7—C8	1.3943 (16)
C1—C6	1.374 (2)	C7—H7A	0.9500
C1—C2	1.382 (2)	C8—C9	1.387 (2)
C2—C3	1.3858 (18)	C9—C7i	1.389 (2)
C2—H2A	0.9500	C9—H9A	0.9500
C3—C4	1.3936 (16)
O3—S1—O2	119.57 (6)	C5—C4—C3	121.74 (11)
O3—S1—O1	108.83 (6)	C5—C4—S1	119.61 (9)
O2—S1—O1	103.25 (5)	C3—C4—S1	118.64 (8)
O3—S1—C4	109.11 (5)	C6—C5—C4	119.12 (12)
O2—S1—C4	109.49 (5)	C6—C5—H5A	120.4
O1—S1—C4	105.62 (5)	C4—C5—H5A	120.4
C8—O1—S1	120.53 (7)	C1—C6—C5	118.09 (12)
C8—O1—H1N1	107.7	C1—C6—H6A	121.0
S1—O1—H1N1	113.2	C5—C6—H6A	121.0
F1—C1—C6	118.34 (13)	C9i—C7—C8	118.74 (13)
F1—C1—C2	117.73 (13)	C9i—C7—H7A	120.6
C6—C1—C2	123.93 (12)	C8—C7—H7A	120.6
C1—C2—C3	117.99 (12)	C9—C8—C7	121.28 (12)
C1—C2—H2A	121.0	C9—C8—O1	117.95 (10)
C3—C2—H2A	121.0	C7—C8—O1	120.67 (13)
C2—C3—C4	119.13 (11)	C8—C9—C7i	119.98 (11)
C2—C3—H3A	120.4	C8—C9—H9A	120.0
C4—C3—H3A	120.4	C7i—C9—H9A	120.0
O3—S1—O1—C8	59.87 (10)	O1—S1—C4—C3	−71.39 (10)
O2—S1—O1—C8	−172.10 (9)	C3—C4—C5—C6	−0.18 (18)
C4—S1—O1—C8	−57.16 (10)	S1—C4—C5—C6	−179.74 (10)
F1—C1—C2—C3	178.60 (12)	F1—C1—C6—C5	−178.59 (12)
C6—C1—C2—C3	−0.7 (2)	C2—C1—C6—C5	0.7 (2)
C1—C2—C3—C4	0.23 (19)	C4—C5—C6—C1	−0.25 (19)
C2—C3—C4—C5	0.18 (18)	C9i—C7—C8—C9	−0.15 (19)
C2—C3—C4—S1	179.75 (10)	C9i—C7—C8—O1	−176.54 (11)
O3—S1—C4—C5	−8.66 (11)	S1—O1—C8—C9	122.24 (11)
O2—S1—C4—C5	−141.24 (9)	S1—O1—C8—C7	−61.25 (13)
O1—S1—C4—C5	108.18 (10)	C7—C8—C9—C7i	0.2 (2)
O3—S1—C4—C3	171.77 (9)	O1—C8—C9—C7i	176.64 (11)
O2—S1—C4—C3	39.18 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2ii	0.96	2.12	3.0630 (14)	169
C5—H5A···F1iii	0.95	2.37	3.2766 (16)	159
C6—H6A···O3iv	0.95	2.54	3.4130 (17)	152
C7—H7A···O2v	0.95	2.60	3.3936 (17)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2i	0.96	2.12	3.0630 (14)	169
C5—H5A⋯F1ii	0.95	2.37	3.2766 (16)	159
C6—H6A⋯O3iii	0.95	2.54	3.4130 (17)	152
C7—H7A⋯O2iv	0.95	2.60	3.3936 (17)	142

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