Bis(4-sulfamoylanilinium) sulfate.

In the title salt, 2C6H9N2O2S(+)·SO4 (2-), the sulfate S atom is situated on a crystallographic twofold axis (the symmetry of the anion is 2). The anion exerts intense libration, which is manifested by shortening of the observed sulfate S-O bonds, as well as by features in the electron-density map. The crystal structure is stabilized through a three-dimensional hydrogen-bonding network formed by strong N-H⋯O hydrogen bonds.

Related literature

For information about folate synthesis, see: Kent (2000 ▶). For related structures, see: Pandiarajan et al. (2011 ▶); Zaouali Zgolli et al. (2010 ▶). For correction of the S—O distances in the sulfate anion due to libration movement, see: Nardelli (1995 ▶). For TLS approximation, see: Schomaker & Trueblood (1968 ▶). For graph-set motifs, see: Etter et al. (1990 ▶). For the categorization of hydrogen bonds, see: Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

2C6H9N2O2S+·SO4 2−

M = 442.48

Orthorhombic,

a = 9.6543 (6) Å

b = 9.7591 (11) Å

c = 18.579 (3) Å

V = 1750.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 293 K

0.24 × 0.22 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

18054 measured reflections

2054 independent reflections

1950 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.104

S = 1.05

2054 reflections

131 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.69 e Å−3

Δρmin = −0.51 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL/PC and JANA2006 (Petricek et al., 2006 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and JANA2006; software used to prepare material for publication: SHELXTL/PC.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007216/fb2278sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007216/fb2278Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007216/fb2278Isup3.cml

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

2C6H9N2O2S+·SO42−	F(000) = 920
Mr = 442.48	Dx = 1.679 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2417 reflections
a = 9.6543 (6) Å	θ = 2.4–23.9°
b = 9.7591 (11) Å	µ = 0.48 mm−1
c = 18.579 (3) Å	T = 293 K
V = 1750.5 (4) Å3	Block, colourless
Z = 4	0.24 × 0.22 × 0.19 mm

Bruker SMART APEX CCD area-detector diffractometer	1950 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 27.8°, θmin = 2.2°
ω scans	h = −12→12
18054 measured reflections	k = −12→12
2054 independent reflections	l = −24→23

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0478P)2 + 1.7836P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2054 reflections	Δρmax = 0.69 e Å−3
131 parameters	Δρmin = −0.51 e Å−3
2 restraints	Extinction correction: SHELXTL/PC (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
29 constraints	Extinction coefficient: 0.048 (2)
Primary atom site location: structure-invariant direct methods

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.11530 (19)	0.63165 (19)	0.54983 (9)	0.0275 (4)
C2	0.0350 (2)	0.6931 (2)	0.49691 (11)	0.0346 (4)
H2	−0.0419	0.7451	0.5098	0.041*
C3	0.0693 (2)	0.6772 (2)	0.42437 (10)	0.0349 (4)
H3	0.0161	0.7185	0.3887	0.042*
C4	0.18330 (18)	0.59911 (18)	0.40639 (9)	0.0278 (4)
C5	0.2642 (2)	0.5368 (2)	0.45866 (10)	0.0363 (4)
H5	0.3407	0.4846	0.4455	0.044*
C6	0.2300 (2)	0.5530 (2)	0.53135 (10)	0.0368 (4)
H6	0.2833	0.5115	0.5669	0.044*
N1	0.1578 (2)	0.7855 (2)	0.66870 (10)	0.0418 (4)
H1N	0.234 (2)	0.771 (3)	0.6883 (13)	0.050*
H2N	0.118 (3)	0.863 (2)	0.6780 (15)	0.050*
N2	0.21752 (18)	0.57958 (18)	0.32972 (8)	0.0343 (4)
H2A	0.1882	0.6516	0.3046	0.052*
H2B	0.1762	0.5041	0.3135	0.052*
H2C	0.3088	0.5712	0.3248	0.052*
S1	0.07157 (5)	0.65527 (5)	0.64256 (2)	0.02962 (17)
O1	0.11508 (19)	0.53240 (16)	0.68009 (8)	0.0447 (4)
O2	−0.07144 (14)	0.69235 (18)	0.64486 (8)	0.0401 (4)
S2	0.5000	0.61321 (7)	0.7500	0.0330 (2)
O21	0.5039 (2)	0.52764 (18)	0.68459 (10)	0.0586 (5)
O22	0.6198 (3)	0.7004 (3)	0.75120 (13)	0.1099 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0286 (8)	0.0291 (8)	0.0249 (8)	−0.0019 (7)	0.0024 (7)	−0.0003 (6)
C2	0.0336 (9)	0.0373 (10)	0.0328 (9)	0.0103 (8)	0.0029 (8)	0.0007 (8)
C3	0.0359 (10)	0.0398 (10)	0.0291 (9)	0.0076 (8)	−0.0016 (7)	0.0055 (8)
C4	0.0298 (8)	0.0287 (8)	0.0249 (8)	−0.0040 (7)	0.0036 (6)	−0.0001 (6)
C5	0.0325 (9)	0.0433 (11)	0.0330 (9)	0.0102 (8)	0.0046 (8)	0.0015 (8)
C6	0.0343 (10)	0.0469 (11)	0.0293 (9)	0.0109 (8)	0.0000 (7)	0.0046 (8)
N1	0.0381 (9)	0.0407 (10)	0.0465 (10)	−0.0023 (8)	−0.0103 (8)	−0.0076 (8)
N2	0.0371 (9)	0.0398 (9)	0.0261 (7)	−0.0027 (7)	0.0044 (6)	−0.0013 (6)
S1	0.0324 (3)	0.0309 (3)	0.0255 (2)	−0.00172 (17)	0.00340 (16)	−0.00089 (16)
O1	0.0638 (10)	0.0385 (8)	0.0317 (7)	0.0043 (7)	0.0071 (7)	0.0072 (6)
O2	0.0300 (7)	0.0514 (9)	0.0389 (8)	−0.0028 (6)	0.0067 (6)	−0.0093 (6)
S2	0.0239 (3)	0.0230 (3)	0.0521 (4)	0.000	−0.0031 (3)	0.000
O21	0.0739 (12)	0.0411 (9)	0.0606 (11)	−0.0021 (8)	0.0280 (9)	−0.0121 (8)
O22	0.0993 (18)	0.142 (2)	0.0884 (16)	−0.0935 (18)	−0.0563 (14)	0.0677 (16)

C1—C2	1.389 (3)	N1—S1	1.5950 (19)
C1—C6	1.390 (3)	N1—H1N	0.834 (17)
C1—S1	1.7887 (18)	N1—H2N	0.866 (17)
C2—C3	1.397 (3)	N2—H2A	0.8900
C2—H2	0.9300	N2—H2B	0.8900
C3—C4	1.379 (3)	N2—H2C	0.8900
C3—H3	0.9300	S1—O2	1.4279 (15)
C4—C5	1.386 (3)	S1—O1	1.4494 (15)
C4—N2	1.475 (2)	S2—O22i	1.4362 (19)
C5—C6	1.399 (3)	S2—O22	1.436 (2)
C5—H5	0.9300	S2—O21i	1.4750 (18)
C6—H6	0.9300	S2—O21	1.4751 (18)
C2—C1—C6	120.56 (17)	H1N—N1—H2N	117 (3)
C2—C1—S1	119.64 (14)	C4—N2—H2A	109.5
C6—C1—S1	119.80 (14)	C4—N2—H2B	109.5
C1—C2—C3	120.16 (17)	H2A—N2—H2B	109.5
C1—C2—H2	119.9	C4—N2—H2C	109.5
C3—C2—H2	119.9	H2A—N2—H2C	109.5
C4—C3—C2	119.00 (17)	H2B—N2—H2C	109.5
C4—C3—H3	120.5	O2—S1—O1	118.39 (10)
C2—C3—H3	120.5	O2—S1—N1	107.08 (10)
C3—C4—C5	121.45 (17)	O1—S1—N1	111.18 (11)
C3—C4—N2	118.95 (16)	O2—S1—C1	106.84 (9)
C5—C4—N2	119.59 (17)	O1—S1—C1	106.76 (9)
C4—C5—C6	119.60 (18)	N1—S1—C1	105.83 (10)
C4—C5—H5	120.2	O22i—S2—O22	107.4 (3)
C6—C5—H5	120.2	O22i—S2—O21i	109.11 (16)
C1—C6—C5	119.24 (17)	O22—S2—O21i	110.07 (12)
C1—C6—H6	120.4	O22i—S2—O21	110.07 (12)
C5—C6—H6	120.4	O22—S2—O21	109.11 (16)
S1—N1—H1N	117.4 (19)	O21i—S2—O21	111.04 (16)
S1—N1—H2N	121.8 (19)
C6—C1—C2—C3	−0.4 (3)	S1—C1—C6—C5	−179.13 (16)
S1—C1—C2—C3	179.02 (16)	C4—C5—C6—C1	−0.1 (3)
C1—C2—C3—C4	0.3 (3)	C2—C1—S1—O2	21.96 (19)
C2—C3—C4—C5	−0.2 (3)	C6—C1—S1—O2	−158.59 (17)
C2—C3—C4—N2	178.55 (18)	C2—C1—S1—O1	149.55 (17)
C3—C4—C5—C6	0.1 (3)	C6—C1—S1—O1	−31.01 (19)
N2—C4—C5—C6	−178.65 (18)	C2—C1—S1—N1	−91.92 (18)
C2—C1—C6—C5	0.3 (3)	C6—C1—S1—N1	87.52 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O22i	0.84 (2)	1.93 (2)	2.743 (3)	164 (3)
N1—H2N···O21ii	0.86 (2)	1.99 (2)	2.849 (3)	168 (3)
N2—H2B···O2iii	0.89	2.30	3.043 (3)	141
N2—H2B···O1iv	0.89	2.57	3.146 (2)	123
N2—H2A···O22v	0.89	1.90	2.787 (3)	177
N2—H2C···O21vi	0.89	2.06	2.900 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O22i	0.84 (2)	1.93 (2)	2.743 (3)	164 (3)
N1—H2N⋯O21ii	0.86 (2)	1.99 (2)	2.849 (3)	168 (3)
N2—H2B⋯O2iii	0.89	2.30	3.043 (3)	141
N2—H2B⋯O1iv	0.89	2.57	3.146 (2)	123
N2—H2A⋯O22v	0.89	1.90	2.787 (3)	177
N2—H2C⋯O21vi	0.89	2.06	2.900 (3)	158

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