Crystal structure of 4-sulfamoylanilinium di-hydrogen phosphate.

In the crystal structure of the title mol-ecular salt, C6H9N2O2S(+)·H2PO4 (-), the sulfomylalinium cations and the di-hydrogen phosphate anions form independent [100] chains through Ns-H⋯O (s = sulfamo-yl) and O-H⋯O hydrogen bonds, respectively. The chains are cross-linked by Na-H⋯O (a = amine) hydrogen bonds, generating (010) sheets. Two C-H⋯O hydrogen bonds involving diametrically opposite C atoms in the benzene ring of the cation as donors form chains parallel to [202] in which P=O and P-OH groups are acceptors. Together, these inter-actions lead to a three-dimensional network.

Related literature

For background to pan class="Chemical">sulfan> drugs, see: Topacli & Kesimli (2001 ▶); Gelbrich et al. (2007 ▶). For structures of other mol­ecular pan class="Chemical">salts of the same cation, see: Anitha et al. (2013 ▶); Ravikumar et al. (2013 ▶); Pandiarajan et al. (2011 ▶); Zaouali Zgolli et al. (2010 ▶); Gelbrich et al. (2008 ▶); Chatterjee et al. (1981 ▶).

Experimental

Crystal data

C6pan class="Species">H9N2n>O2S+·pan class="Chemical">H2O4P−

M = 270.20

Monoclinic,

a = 4.8041 (7) Å

b = 10.8564 (15) Å

c = 10.3862 (15) Å

β = 101.067 (2)°

V = 531.62 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.47 mm−1

T = 294 K

0.28 × 0.18 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.94, T max = 0.99

6033 measured reflections

2512 independent reflections

2502 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.055

S = 1.06

2512 reflections

174 parameters

4 restraints

pan class="Disease">H atomsn> treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack x determined using 1209 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons & Flack, 2004 ▶)

Absolute structure parameter: 0.069 (16)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); n class="Chemical">program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL2013.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814017462/hb7251sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814017462/hb7251Isup2.hkl

Click here for additional data file.

Supn class="Chemical">porting information file. DOI: 10.1107/S1600536814017462/hb7251Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814017462/hb7251fig1.tif

Mol­ecular structure of (I) showing displacement ellin class="Chemical">psoids drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814017462/hb7251fig2.tif

pan class="Chemical">Hydrogenn>-bonding environment of the di­pan class="Chemical">hydrogen phosphate anion viewed along the b-axis. Other pan class="Chemical">hydrogen bonds involving N atom and non-participating H atoms have been omitted for clarity.

CCDC reference: 1016950

Additional supporting information: crystallographic information; 3D view; checkCIF report

C6H9N2O2S+·H2O4P−	Z = 2
Mr = 270.20	F(000) = 280
Monoclinic, Pc	Dx = 1.688 Mg m−3
a = 4.8041 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8564 (15) Å	µ = 0.47 mm−1
c = 10.3862 (15) Å	T = 294 K
β = 101.067 (2)°	Needle, colourless
V = 531.62 (13) Å3	0.28 × 0.18 × 0.10 mm

Bruker SMART APEX CCD diffractometer	2502 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.018
Absorption correction: multi-scan (SADABS; Bruker, 2001)	θmax = 28.3°, θmin = 1.9°
Tmin = 0.94, Tmax = 0.99	h = −6→6
6033 measured reflections	k = −14→14
2512 independent reflections	l = −13→13

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0415P)2 + 0.0212P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.021	(Δ/σ)max < 0.001
wR(F2) = 0.055	Δρmax = 0.20 e Å−3
S = 1.06	Δρmin = −0.22 e Å−3
2512 reflections	Extinction correction: SHELXL2013 (Sheldrick, 2013), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
174 parameters	Extinction coefficient: 0.099 (8)
4 restraints	Absolute structure: Flack x determined using 1209 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
Hydrogen site location: mixed	Absolute structure parameter: 0.069 (16)

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.

	x	y	z	Uiso*/Ueq
C1	0.8098 (4)	0.14923 (16)	0.09044 (19)	0.0265 (3)
C2	1.0153 (5)	0.1497 (2)	0.2035 (2)	0.0365 (5)
H2	1.1473	0.0862	0.2199	0.044*
C3	1.0231 (5)	0.2455 (2)	0.2922 (2)	0.0364 (5)
H3	1.1623	0.2475	0.3680	0.044*
C4	0.8220 (4)	0.33816 (17)	0.26728 (19)	0.0271 (4)
C5	0.6183 (5)	0.3379 (2)	0.1532 (2)	0.0381 (5)
H5	0.4862	0.4013	0.1368	0.046*
C6	0.6116 (5)	0.2433 (2)	0.0639 (2)	0.0379 (5)
H6	0.4759	0.2426	−0.0132	0.046*
N1	0.7938 (4)	0.04600 (14)	−0.00122 (17)	0.0271 (3)
N2	0.9589 (4)	0.57959 (17)	0.3299 (2)	0.0352 (4)
O6	0.3160 (3)	0.08705 (13)	0.55239 (13)	0.0288 (3)
O5	0.7279 (3)	0.12348 (14)	0.74157 (13)	0.0298 (3)
O3	0.4839 (5)	0.30112 (15)	0.62757 (19)	0.0504 (5)
O4	0.2474 (3)	0.1676 (2)	0.77341 (17)	0.0506 (5)
O1	1.0051 (4)	0.42220 (15)	0.50222 (15)	0.0364 (3)
O2	0.5320 (3)	0.48636 (17)	0.38326 (17)	0.0400 (4)
P1	0.44104 (7)	0.16369 (4)	0.66908 (4)	0.02196 (12)
S1	0.82319 (8)	0.45858 (4)	0.38175 (5)	0.02634 (13)
H1A	0.760 (7)	0.072 (3)	−0.082 (3)	0.039 (7)*
H1B	0.639 (8)	0.001 (3)	0.006 (3)	0.046 (8)*
H1C	0.946 (8)	0.003 (3)	0.018 (3)	0.046 (8)*
H2A	0.855 (8)	0.611 (3)	0.261 (3)	0.050 (9)*
H2B	1.143 (8)	0.578 (3)	0.333 (3)	0.042 (8)*
H3A	0.343 (6)	0.334 (3)	0.594 (4)	0.052 (10)*
H4A	0.083 (6)	0.164 (4)	0.742 (4)	0.080 (14)*

	U11	U22	U33	U12	U13	U23
C1	0.0272 (8)	0.0273 (8)	0.0245 (8)	−0.0007 (7)	0.0037 (7)	0.0024 (6)
C2	0.0368 (11)	0.0306 (9)	0.0372 (10)	0.0102 (8)	−0.0053 (9)	−0.0037 (8)
C3	0.0362 (11)	0.0335 (10)	0.0336 (10)	0.0084 (8)	−0.0084 (8)	−0.0030 (8)
C4	0.0288 (9)	0.0255 (8)	0.0270 (8)	0.0011 (6)	0.0052 (7)	0.0007 (6)
C5	0.0395 (11)	0.0363 (10)	0.0344 (10)	0.0145 (8)	−0.0036 (9)	0.0009 (8)
C6	0.0402 (11)	0.0400 (11)	0.0288 (9)	0.0105 (8)	−0.0053 (7)	−0.0011 (8)
N1	0.0287 (8)	0.0275 (7)	0.0243 (7)	−0.0007 (6)	0.0035 (6)	0.0016 (6)
N2	0.0310 (9)	0.0275 (8)	0.0462 (10)	0.0021 (7)	0.0050 (7)	0.0048 (7)
O6	0.0273 (6)	0.0314 (7)	0.0262 (6)	−0.0009 (5)	0.0014 (5)	−0.0035 (5)
O5	0.0189 (6)	0.0402 (8)	0.0290 (6)	0.0020 (5)	0.0017 (5)	0.0063 (6)
O3	0.0514 (10)	0.0261 (7)	0.0608 (11)	−0.0079 (7)	−0.0212 (8)	0.0091 (7)
O4	0.0195 (7)	0.0980 (15)	0.0357 (9)	−0.0113 (7)	0.0086 (6)	−0.0243 (8)
O1	0.0389 (8)	0.0414 (8)	0.0276 (6)	0.0079 (7)	0.0031 (6)	0.0013 (6)
O2	0.0250 (7)	0.0473 (8)	0.0492 (9)	0.0050 (6)	0.0107 (6)	−0.0059 (7)
P1	0.01703 (19)	0.0251 (2)	0.0230 (2)	−0.00087 (15)	0.00186 (14)	−0.00013 (15)
S1	0.0230 (2)	0.0275 (2)	0.0287 (2)	0.00361 (16)	0.00527 (14)	0.00025 (15)

C1—C2	1.381 (3)	N1—H1B	0.90 (4)
C1—C6	1.387 (3)	N1—H1C	0.86 (4)
C1—N1	1.463 (2)	N2—S1	1.6048 (19)
C2—C3	1.386 (3)	N2—H2A	0.86 (3)
C2—H2	0.9300	N2—H2B	0.88 (4)
C3—C4	1.384 (3)	O6—P1	1.4975 (14)
C3—H3	0.9300	O5—P1	1.5027 (13)
C4—C5	1.384 (3)	O3—P1	1.5774 (17)
C4—S1	1.7665 (19)	O3—H3A	0.78 (2)
C5—C6	1.380 (3)	O4—P1	1.5583 (16)
C5—H5	0.9300	O4—H4A	0.80 (3)
C6—H6	0.9300	O1—S1	1.4371 (16)
N1—H1A	0.87 (3)	O2—S1	1.4339 (15)
C2—C1—C6	121.19 (18)	C1—N1—H1C	109 (2)
C2—C1—N1	119.70 (18)	H1A—N1—H1C	113 (3)
C6—C1—N1	119.08 (18)	H1B—N1—H1C	111 (3)
C1—C2—C3	119.45 (19)	S1—N2—H2A	113 (2)
C1—C2—H2	120.3	S1—N2—H2B	116 (2)
C3—C2—H2	120.3	H2A—N2—H2B	117 (3)
C4—C3—C2	119.49 (19)	P1—O3—H3A	114 (3)
C4—C3—H3	120.3	P1—O4—H4A	113 (3)
C2—C3—H3	120.3	O6—P1—O5	115.53 (9)
C3—C4—C5	120.79 (18)	O6—P1—O4	112.17 (9)
C3—C4—S1	120.00 (16)	O5—P1—O4	105.78 (9)
C5—C4—S1	119.21 (15)	O6—P1—O3	110.94 (9)
C6—C5—C4	119.90 (19)	O5—P1—O3	104.87 (10)
C6—C5—H5	120.0	O4—P1—O3	106.92 (13)
C4—C5—H5	120.0	O2—S1—O1	118.66 (10)
C5—C6—C1	119.15 (19)	O2—S1—N2	106.94 (11)
C5—C6—H6	120.4	O1—S1—N2	107.39 (11)
C1—C6—H6	120.4	O2—S1—C4	106.61 (10)
C1—N1—H1A	110.5 (19)	O1—S1—C4	107.79 (10)
C1—N1—H1B	108 (2)	N2—S1—C4	109.21 (10)
H1A—N1—H1B	105 (3)
C6—C1—C2—C3	0.3 (4)	C2—C1—C6—C5	−0.9 (3)
N1—C1—C2—C3	−177.7 (2)	N1—C1—C6—C5	177.0 (2)
C1—C2—C3—C4	1.0 (4)	C3—C4—S1—O2	−142.11 (19)
C2—C3—C4—C5	−1.7 (4)	C5—C4—S1—O2	37.8 (2)
C2—C3—C4—S1	178.21 (19)	C3—C4—S1—O1	−13.7 (2)
C3—C4—C5—C6	1.1 (4)	C5—C4—S1—O1	166.24 (18)
S1—C4—C5—C6	−178.88 (19)	C3—C4—S1—N2	102.68 (19)
C4—C5—C6—C1	0.3 (4)	C5—C4—S1—N2	−77.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5i	0.87 (3)	1.89 (3)	2.760 (2)	174 (3)
N1—H1B···O6ii	0.90 (4)	1.96 (4)	2.856 (2)	170 (3)
N1—H1C···O6iii	0.86 (4)	2.00 (4)	2.855 (2)	175 (3)
N2—H2A···O3iv	0.86 (3)	2.25 (4)	3.076 (3)	161 (3)
N2—H2B···O2v	0.88 (4)	2.10 (4)	2.886 (3)	149 (3)
O3—H3A···O1vi	0.78 (2)	1.97 (2)	2.750 (3)	176 (4)
O4—H4A···O5vi	0.80 (3)	1.76 (3)	2.500 (2)	154 (5)
C3—H3···O6v	0.93	2.59	3.283 (3)	132
C6—H6···O4i	0.93	2.42	3.288 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5i	0.87 (3)	1.89 (3)	2.760 (2)	174 (3)
N1—H1B⋯O6ii	0.90 (4)	1.96 (4)	2.856 (2)	170 (3)
N1—H1C⋯O6iii	0.86 (4)	2.00 (4)	2.855 (2)	175 (3)
N2—H2A⋯O3iv	0.86 (3)	2.25 (4)	3.076 (3)	161 (3)
N2—H2B⋯O2v	0.88 (4)	2.10 (4)	2.886 (3)	149 (3)
O3—H3A⋯O1vi	0.78 (2)	1.97 (2)	2.750 (3)	176 (4)
O4—H4A⋯O5vi	0.80 (3)	1.76 (3)	2.500 (2)	154 (5)
C3—H3⋯O6v	0.93	2.59	3.283 (3)	132
C6—H6⋯O4i	0.93	2.42	3.288 (3)	156

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