Polymorphic form II of 4,4'-methyl-enebis(benzene-sulfonamide).

In the title compound, C(13)H(14)N(2)O(4)S(2) (alternative names: diphenyl-methane-4,4'-disulfonamide, nirexon, CRN: 535-66-0), the two benzene rings form a dihedral angle of 70.8 (1)°. There are two sets of shorter (H⋯O < 2.1 Å) and longer (H⋯O > 2.4 Å) N-H⋯O hydrogen bonds per sulfonamide NH(2) group, which together result in hydrogen-bonded sheets parallel (102). Adjacent sheets are connected to one another by an additional N-H⋯N inter-action so that a three-dimensional network of hydrogen-bonded mol-ecules is formed. The investigated polymorph is identical with the form II previously described by Kuhnert-Brandstätter & Moser [(1981). Mikrochim. Acta, 75, 421-440].

Related literature

For the polymorphism of diphenyl­methane-4,4′-disulfonamide, see Kuhnert-Brandstätter & Moser (1981 ▶); Kuhnert-Brandstätter & Wunsch (1969 ▶).

Experimental

Crystal data

C13H14N2O4S2

M = 326.38

Monoclinic,

a = 10.8251 (5) Å

b = 5.0791 (3) Å

c = 12.6912 (5) Å

β = 90.931 (3)°

V = 697.69 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.40 mm−1

T = 120 K

0.25 × 0.1 × 0.05 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.907, T max = 0.980

7877 measured reflections

2438 independent reflections

2152 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.087

S = 1.06

2438 reflections

216 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.46 e Å−3

Absolute structure: Flack (1983 ▶), 904 Friedel pairs

Flack parameter: −0.18 (9)

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021409/im2209sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021409/im2209Isup2.hkl

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

C13H14N2O4S2	F(000) = 340
Mr = 326.38	Dx = 1.554 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6304 reflections
a = 10.8251 (5) Å	θ = 2.9–26.0°
b = 5.0791 (3) Å	µ = 0.40 mm−1
c = 12.6912 (5) Å	T = 120 K
β = 90.931 (3)°	Needle, colourless
V = 697.69 (6) Å3	0.25 × 0.1 × 0.05 mm
Z = 2

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	2438 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	2152 reflections with I > 2σ(I)
graphite	Rint = 0.054
Detector resolution: 9.091 pixels mm-1	θmax = 26.0°, θmin = 3.7°
φ & ω scans	h = −13→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −5→6
Tmin = 0.907, Tmax = 0.980	l = −15→15
7877 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0361P)2 + 0.182P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2438 reflections	Δρmax = 0.26 e Å−3
216 parameters	Δρmin = −0.46 e Å−3
5 restraints	Absolute structure: Flack (1983), 904 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.18 (9)

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
S1	0.20189 (6)	−0.23188 (15)	0.54432 (5)	0.01593 (18)
S2	0.88754 (6)	0.73072 (17)	0.14221 (5)	0.01695 (19)
O1	0.1335 (2)	−0.4632 (4)	0.51332 (16)	0.0205 (5)
O2	0.30683 (18)	−0.2579 (6)	0.61295 (14)	0.0238 (5)
O3	0.90887 (19)	0.8314 (5)	0.03829 (15)	0.0249 (6)
O4	0.90645 (19)	0.9060 (4)	0.23016 (16)	0.0208 (5)
N1	0.1033 (3)	−0.0417 (6)	0.6023 (2)	0.0189 (6)
H1	0.035 (3)	−0.039 (10)	0.563 (3)	0.053 (13)*
H2	0.129 (3)	0.124 (4)	0.608 (3)	0.035 (11)*
N2	0.9759 (2)	0.4794 (6)	0.1575 (2)	0.0197 (6)
H3	0.994 (3)	0.410 (7)	0.0960 (18)	0.030 (10)*
H4	0.965 (3)	0.381 (7)	0.213 (2)	0.042 (12)*
C1	0.3517 (3)	0.3849 (7)	0.1577 (2)	0.0208 (7)
H1A	0.3319	0.2784	0.0943	0.024 (8)*
H1B	0.2990	0.5441	0.1550	0.028 (10)*
C11	0.2504 (3)	−0.0654 (6)	0.4304 (2)	0.0169 (7)
C12	0.1806 (3)	−0.0834 (7)	0.3372 (2)	0.0212 (7)
H12	0.1097	−0.1934	0.3335	0.021 (8)*
C13	0.2160 (3)	0.0610 (7)	0.2502 (2)	0.0200 (7)
H13	0.1696	0.0470	0.1863	0.032 (10)*
C14	0.3184 (2)	0.2261 (7)	0.2547 (2)	0.0164 (6)
C15	0.3882 (2)	0.2386 (8)	0.3479 (2)	0.0189 (6)
H15	0.4599	0.3463	0.3514	0.045 (12)*
C16	0.3538 (3)	0.0945 (7)	0.4360 (2)	0.0188 (7)
H16	0.4011	0.1058	0.4995	0.026 (9)*
C21	0.7330 (3)	0.6228 (6)	0.1479 (2)	0.0151 (6)
C22	0.6511 (2)	0.7639 (7)	0.2093 (2)	0.0174 (6)
H22	0.6786	0.9108	0.2497	0.037 (11)*
C23	0.5271 (3)	0.6854 (6)	0.2106 (2)	0.0179 (7)
H23	0.4702	0.7814	0.2520	0.021 (8)*
C24	0.4857 (3)	0.4701 (6)	0.1528 (2)	0.0170 (7)
C25	0.5703 (3)	0.3302 (7)	0.0928 (2)	0.0183 (7)
H25	0.5432	0.1810	0.0536	0.030 (10)*
C26	0.6932 (3)	0.4053 (7)	0.0892 (2)	0.0187 (7)
H26	0.7498	0.3100	0.0473	0.043 (11)*

	U11	U22	U33	U12	U13	U23
S1	0.0169 (3)	0.0134 (4)	0.0174 (3)	−0.0005 (4)	0.0005 (2)	0.0018 (4)
S2	0.0179 (4)	0.0157 (4)	0.0174 (3)	−0.0004 (4)	0.0033 (3)	0.0020 (4)
O1	0.0255 (12)	0.0093 (11)	0.0268 (12)	−0.0053 (10)	0.0004 (9)	−0.0009 (10)
O2	0.0203 (10)	0.0268 (13)	0.0241 (10)	−0.0016 (12)	−0.0057 (8)	0.0087 (13)
O3	0.0256 (12)	0.0306 (15)	0.0187 (10)	0.0016 (10)	0.0085 (8)	0.0113 (10)
O4	0.0222 (11)	0.0154 (12)	0.0249 (11)	−0.0026 (10)	0.0013 (9)	−0.0060 (10)
N1	0.0232 (15)	0.0143 (15)	0.0193 (14)	0.0003 (13)	0.0061 (11)	−0.0001 (12)
N2	0.0231 (14)	0.0191 (16)	0.0170 (14)	0.0058 (13)	0.0049 (11)	0.0032 (12)
C1	0.0209 (16)	0.0217 (18)	0.0196 (16)	−0.0019 (15)	−0.0019 (12)	0.0066 (14)
C11	0.0178 (15)	0.0145 (16)	0.0183 (14)	0.0002 (14)	0.0012 (12)	0.0014 (13)
C12	0.0173 (16)	0.0217 (19)	0.0246 (16)	−0.0055 (15)	−0.0045 (12)	0.0016 (15)
C13	0.0184 (16)	0.0229 (18)	0.0186 (15)	−0.0020 (15)	−0.0032 (12)	0.0005 (14)
C14	0.0155 (14)	0.0149 (16)	0.0189 (13)	0.0007 (15)	0.0011 (10)	0.0006 (15)
C15	0.0176 (14)	0.0204 (16)	0.0188 (13)	−0.0024 (17)	0.0009 (11)	0.0022 (17)
C16	0.0178 (16)	0.0191 (17)	0.0194 (15)	−0.0032 (14)	−0.0010 (12)	−0.0008 (13)
C21	0.0169 (15)	0.0134 (16)	0.0153 (13)	0.0005 (13)	0.0031 (11)	0.0024 (13)
C22	0.0228 (15)	0.0124 (15)	0.0169 (13)	−0.0014 (15)	−0.0009 (11)	0.0002 (16)
C23	0.0184 (15)	0.0181 (18)	0.0174 (14)	0.0015 (13)	0.0054 (12)	−0.0014 (13)
C24	0.0222 (16)	0.0168 (17)	0.0118 (14)	0.0009 (14)	−0.0020 (12)	0.0076 (13)
C25	0.0244 (16)	0.0183 (18)	0.0123 (13)	−0.0037 (13)	−0.0008 (12)	−0.0027 (12)
C26	0.0245 (16)	0.0153 (17)	0.0163 (14)	0.0028 (15)	0.0019 (12)	0.0002 (14)

S1—O2	1.4263 (19)	C12—C13	1.385 (4)
S1—O1	1.440 (2)	C12—H12	0.9500
S1—N1	1.624 (3)	C13—C14	1.390 (4)
S1—C11	1.762 (3)	C13—H13	0.9500
S2—O3	1.437 (2)	C14—C15	1.395 (4)
S2—O4	1.440 (2)	C15—C16	1.391 (4)
S2—N2	1.605 (3)	C15—H15	0.9500
S2—C21	1.763 (3)	C16—H16	0.9500
N1—H1	0.881 (19)	C21—C22	1.389 (4)
N1—H2	0.887 (19)	C21—C26	1.397 (4)
N2—H3	0.883 (18)	C22—C23	1.401 (4)
N2—H4	0.875 (19)	C22—H22	0.9500
C1—C24	1.516 (4)	C23—C24	1.387 (4)
C1—C14	1.520 (4)	C23—H23	0.9500
C1—H1A	0.9900	C24—C25	1.395 (4)
C1—H1B	0.9900	C25—C26	1.386 (4)
C11—C16	1.384 (4)	C25—H25	0.9500
C11—C12	1.396 (4)	C26—H26	0.9500
O2—S1—O1	119.49 (15)	C12—C13—C14	121.1 (3)
O2—S1—N1	107.52 (14)	C12—C13—H13	119.4
O1—S1—N1	105.68 (14)	C14—C13—H13	119.4
O2—S1—C11	107.49 (13)	C13—C14—C15	118.9 (3)
O1—S1—C11	109.03 (14)	C13—C14—C1	119.1 (3)
N1—S1—C11	107.02 (15)	C15—C14—C1	122.0 (3)
O3—S2—O4	117.93 (14)	C16—C15—C14	120.6 (3)
O3—S2—N2	106.86 (13)	C16—C15—H15	119.7
O4—S2—N2	108.72 (13)	C14—C15—H15	119.7
O3—S2—C21	108.36 (13)	C11—C16—C15	119.7 (3)
O4—S2—C21	106.48 (13)	C11—C16—H16	120.2
N2—S2—C21	108.18 (15)	C15—C16—H16	120.2
S1—N1—H1	108 (3)	C22—C21—C26	120.9 (3)
S1—N1—H2	114 (2)	C22—C21—S2	118.5 (2)
H1—N1—H2	107 (4)	C26—C21—S2	120.6 (2)
S2—N2—H3	111 (2)	C21—C22—C23	118.7 (3)
S2—N2—H4	118 (3)	C21—C22—H22	120.6
H3—N2—H4	121 (4)	C23—C22—H22	120.6
C24—C1—C14	115.1 (2)	C24—C23—C22	121.3 (3)
C24—C1—H1A	108.5	C24—C23—H23	119.4
C14—C1—H1A	108.5	C22—C23—H23	119.4
C24—C1—H1B	108.5	C23—C24—C25	118.8 (3)
C14—C1—H1B	108.5	C23—C24—C1	120.2 (3)
H1A—C1—H1B	107.5	C25—C24—C1	120.9 (3)
C16—C11—C12	120.5 (3)	C26—C25—C24	121.1 (3)
C16—C11—S1	119.5 (2)	C26—C25—H25	119.4
C12—C11—S1	120.0 (2)	C24—C25—H25	119.4
C13—C12—C11	119.2 (3)	C25—C26—C21	119.2 (3)
C13—C12—H12	120.4	C25—C26—H26	120.4
C11—C12—H12	120.4	C21—C26—H26	120.4

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88 (2)	2.09 (2)	2.960 (4)	168 (4)
N1—H2···O1ii	0.89 (2)	2.42 (3)	3.166 (4)	142 (3)
N1—H2···O4iii	0.89 (2)	2.53 (3)	3.116 (4)	124 (3)
N2—H3···O3iv	0.88 (2)	2.06 (2)	2.898 (3)	159 (3)
N2—H4···N1v	0.88 (2)	2.50 (3)	3.182 (3)	135 (3)
N2—H4···O4vi	0.88 (2)	2.50 (3)	3.149 (4)	131 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88 (2)	2.09 (2)	2.960 (4)	168 (4)
N1—H2⋯O1ii	0.89 (2)	2.42 (3)	3.166 (4)	142 (3)
N1—H2⋯O4iii	0.89 (2)	2.53 (3)	3.116 (4)	124 (3)
N2—H3⋯O3iv	0.88 (2)	2.06 (2)	2.898 (3)	159 (3)
N2—H4⋯N1v	0.88 (2)	2.50 (3)	3.182 (3)	135 (3)
N2—H4⋯O4vi	0.88 (2)	2.50 (3)	3.149 (4)	131 (3)

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