4-(3-Methyl-benzene-sulfonamido)-phenyl 3-methyl-benzene-sulfonate.

The complete mol-ecule of the title compound, C(20)H(19)NO(5)S(2), is generated by a crystallographic twofold axis and the O atom and N-H group attached to the central benzene ring are statistically disordered. The dihedral angle between the central and terminal benzene rings is 56.91 (5)° and that between the terminal benzene rings is 29.80 (5)°. In the crystal, N-H⋯O hydrogen bonding links the mol-ecules into sheets lying parallel to the ab plane.

Related literature

For the biological properties of sulfonyl derivatives, see: Supuran et al. (2003 ▶). For a related structure, see: Sinha et al. (2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H19NO5S2

M = 417.48

Monoclinic,

a = 14.4352 (1) Å

b = 9.1250 (1) Å

c = 15.4402 (2) Å

β = 109.700 (1)°

V = 1914.76 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 100 K

0.41 × 0.34 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.883, T max = 0.926

21937 measured reflections

3533 independent reflections

3249 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.090

S = 1.08

3533 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.40 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/S1600536811054808/hb6544sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054808/hb6544Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811054808/hb6544Isup3.cml

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

C20H19NO5S2	F(000) = 872
Mr = 417.48	Dx = 1.448 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9887 reflections
a = 14.4352 (1) Å	θ = 2.7–32.8°
b = 9.1250 (1) Å	µ = 0.31 mm−1
c = 15.4402 (2) Å	T = 100 K
β = 109.700 (1)°	Block, colourless
V = 1914.76 (4) Å3	0.41 × 0.34 × 0.25 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3533 independent reflections
Radiation source: fine-focus sealed tube	3249 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 33.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −22→19
Tmin = 0.883, Tmax = 0.926	k = −13→13
21937 measured reflections	l = −23→23

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0485P)2 + 1.0937P] where P = (Fo2 + 2Fc2)/3
3533 reflections	(Δ/σ)max = 0.001
128 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.40 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	0.261632 (15)	0.38804 (2)	0.813408 (15)	0.01868 (7)
O1	0.30077 (5)	0.33201 (8)	0.73257 (5)	0.01910 (13)	0.50
N1	0.30077 (5)	0.33201 (8)	0.73257 (5)	0.01910 (13)	0.50
H1	0.2719	0.2309	0.7120	0.023*	0.50
O2	0.15974 (5)	0.34770 (9)	0.78153 (5)	0.02715 (16)
O3	0.28871 (6)	0.53930 (8)	0.83108 (6)	0.02607 (15)
C1	0.43833 (8)	0.12376 (12)	1.06033 (7)	0.02529 (19)
H1A	0.4772	0.0678	1.1116	0.030*
C2	0.46090 (8)	0.27063 (12)	1.05424 (7)	0.0268 (2)
H2A	0.5145	0.3140	1.1012	0.032*
C3	0.40519 (7)	0.35443 (11)	0.97948 (7)	0.02235 (17)
H3A	0.4195	0.4552	0.9750	0.027*
C4	0.32808 (6)	0.28698 (9)	0.91157 (6)	0.01695 (15)
C5	0.30453 (7)	0.14007 (10)	0.91733 (6)	0.01931 (16)
H5A	0.2511	0.0969	0.8701	0.023*
C6	0.35980 (8)	0.05647 (10)	0.99286 (7)	0.02188 (17)
C7	0.33362 (11)	−0.10114 (11)	1.00160 (9)	0.0333 (2)
H7A	0.3116	−0.1471	0.9407	0.050*
H7B	0.2807	−0.1058	1.0279	0.050*
H7C	0.3915	−0.1531	1.0419	0.050*
C8	0.40253 (6)	0.33636 (9)	0.74375 (6)	0.01551 (14)
C9	0.45112 (6)	0.20366 (9)	0.74745 (6)	0.01958 (16)
H9A	0.4176	0.1138	0.7465	0.023*
C12	0.45042 (6)	0.46948 (9)	0.74605 (6)	0.01721 (15)
H12A	0.4160	0.5593	0.7423	0.021*

	U11	U22	U33	U12	U13	U23
S1	0.01452 (11)	0.02118 (11)	0.02237 (11)	0.00479 (7)	0.00888 (8)	0.00390 (7)
O1	0.0117 (3)	0.0267 (3)	0.0194 (3)	0.0003 (2)	0.0059 (2)	0.0029 (2)
N1	0.0117 (3)	0.0267 (3)	0.0194 (3)	0.0003 (2)	0.0059 (2)	0.0029 (2)
O2	0.0132 (3)	0.0395 (4)	0.0301 (4)	0.0052 (3)	0.0090 (3)	0.0047 (3)
O3	0.0290 (4)	0.0177 (3)	0.0358 (4)	0.0067 (3)	0.0166 (3)	0.0039 (3)
C1	0.0242 (4)	0.0312 (5)	0.0205 (4)	0.0031 (4)	0.0076 (3)	0.0049 (3)
C2	0.0220 (4)	0.0330 (5)	0.0220 (4)	−0.0049 (4)	0.0030 (3)	−0.0008 (4)
C3	0.0209 (4)	0.0220 (4)	0.0235 (4)	−0.0041 (3)	0.0066 (3)	−0.0019 (3)
C4	0.0160 (3)	0.0172 (3)	0.0188 (3)	0.0010 (3)	0.0074 (3)	−0.0003 (3)
C5	0.0208 (4)	0.0180 (4)	0.0201 (4)	−0.0017 (3)	0.0081 (3)	−0.0016 (3)
C6	0.0271 (4)	0.0196 (4)	0.0221 (4)	0.0013 (3)	0.0125 (3)	0.0021 (3)
C7	0.0497 (7)	0.0203 (4)	0.0344 (5)	−0.0012 (4)	0.0201 (5)	0.0050 (4)
C8	0.0119 (3)	0.0183 (3)	0.0161 (3)	−0.0001 (3)	0.0044 (3)	0.0026 (3)
C9	0.0171 (4)	0.0143 (3)	0.0236 (4)	−0.0018 (3)	0.0019 (3)	0.0025 (3)
C12	0.0149 (3)	0.0150 (3)	0.0221 (4)	0.0011 (3)	0.0068 (3)	0.0000 (3)

S1—O2	1.4329 (8)	C4—C5	1.3931 (12)
S1—O3	1.4354 (8)	C5—C6	1.3969 (13)
S1—O1	1.6167 (7)	C5—H5A	0.9500
S1—C4	1.7572 (9)	C6—C7	1.5046 (14)
O1—C8	1.4206 (10)	C7—H7A	0.9800
O1—H1	1.0188	C7—H7B	0.9800
C1—C2	1.3899 (15)	C7—H7C	0.9800
C1—C6	1.3968 (15)	C8—C9	1.3909 (12)
C1—H1A	0.9500	C8—C12	1.3921 (12)
C2—C3	1.3922 (14)	C9—C9i	1.3866 (18)
C2—H2A	0.9500	C9—H9A	0.9500
C3—C4	1.3894 (13)	C12—C12i	1.3949 (16)
C3—H3A	0.9500	C12—H12A	0.9500
O2—S1—O3	119.64 (5)	C4—C5—C6	119.72 (9)
O2—S1—O1	103.82 (4)	C4—C5—H5A	120.1
O3—S1—O1	107.89 (4)	C6—C5—H5A	120.1
O2—S1—C4	111.11 (4)	C1—C6—C5	118.30 (9)
O3—S1—C4	107.83 (5)	C1—C6—C7	121.23 (9)
O1—S1—C4	105.59 (4)	C5—C6—C7	120.45 (10)
C8—O1—S1	120.90 (6)	C6—C7—H7A	109.5
C8—O1—H1	111.2	C6—C7—H7B	109.5
S1—O1—H1	108.3	H7A—C7—H7B	109.5
C2—C1—C6	121.55 (9)	C6—C7—H7C	109.5
C2—C1—H1A	119.2	H7A—C7—H7C	109.5
C6—C1—H1A	119.2	H7B—C7—H7C	109.5
C1—C2—C3	120.17 (9)	C9—C8—C12	121.29 (8)
C1—C2—H2A	119.9	C9—C8—O1	117.85 (7)
C3—C2—H2A	119.9	C12—C8—O1	120.78 (8)
C4—C3—C2	118.32 (9)	C9i—C9—C8	119.46 (5)
C4—C3—H3A	120.8	C9i—C9—H9A	120.3
C2—C3—H3A	120.8	C8—C9—H9A	120.3
C3—C4—C5	121.92 (8)	C8—C12—C12i	119.23 (5)
C3—C4—S1	118.94 (7)	C8—C12—H12A	120.4
C5—C4—S1	119.08 (7)	C12i—C12—H12A	120.4
O2—S1—O1—C8	−172.37 (7)	C3—C4—C5—C6	−0.44 (13)
O3—S1—O1—C8	59.70 (8)	S1—C4—C5—C6	176.91 (7)
C4—S1—O1—C8	−55.39 (7)	C2—C1—C6—C5	1.03 (15)
C6—C1—C2—C3	−0.35 (16)	C2—C1—C6—C7	−177.82 (10)
C1—C2—C3—C4	−0.71 (15)	C4—C5—C6—C1	−0.63 (14)
C2—C3—C4—C5	1.11 (14)	C4—C5—C6—C7	178.23 (9)
C2—C3—C4—S1	−176.24 (8)	S1—O1—C8—C9	113.82 (8)
O2—S1—C4—C3	−144.83 (8)	S1—O1—C8—C12	−69.45 (10)
O3—S1—C4—C3	−11.90 (9)	C12—C8—C9—C9i	−0.70 (16)
O1—S1—C4—C3	103.24 (8)	O1—C8—C9—C9i	176.01 (10)
O2—S1—C4—C5	37.75 (8)	C9—C8—C12—C12i	−1.20 (15)
O3—S1—C4—C5	170.68 (7)	O1—C8—C12—C12i	−177.81 (10)
O1—S1—C4—C5	−74.19 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ii	1.02	1.97	2.9854 (11)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	1.02	1.97	2.9854 (11)	178

Symmetry code: (i) .