Dipotassium disulfanilamidate trihydrate.

The asymmetric unit of the title compound, 2K(+)·2C(6)H(7)N(2)O(2)S(-)·3H(2)O, consists of two potassium cations located on mirror planes, one sulfanilamidate anion in a general position and one and a half mol-ecules of water, one of which is also located on a mirror plane. One potassium cation is seven-coordinated by six sulfonyl O atoms and one water mol-ecule, whereas the other is surrounded by six water O atoms and two sulfonyl O atoms. In the crystal structure, the components are connected into polymeric sheets in the bc plane. The two-dimensional structure is consolidated by N-H⋯O, O-H⋯O, O-H⋯N and C-H⋯π inter-actions. The layers are further linked into a three-dimensional network via N-H⋯O, N-H⋯N and O-H⋯N hydrogen bonds.

Related literature

For the structures of similar potassium salts, see: Gowda et al. (2011 ▶) and references cited therein; Moers et al. (2001 ▶). For the structure of sodium sulfanilamide monohydrate, see: Moreno & Alleaume (1968 ▶).

Experimental

Crystal data

2K+·2C6H7N2O2S−·3H2O

M = 474.64

Orthorhombic,

a = 23.8174 (4) Å

b = 10.9141 (2) Å

c = 7.4645 (1) Å

V = 1940.36 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.75 mm−1

T = 100 K

0.33 × 0.27 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.791, T max = 0.929

8594 measured reflections

2157 independent reflections

2149 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.015

wR(F 2) = 0.042

S = 1.11

2157 reflections

145 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 985 Friedel pairs

Flack parameter: 0.04 (3)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811026791/om2446sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026791/om2446Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026791/om2446Isup3.cml

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

2K+·2C6H7N2O2S−·3H2O	F(000) = 984
Mr = 474.64	Dx = 1.625 Mg m−3
Orthorhombic, Cmc21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c -2	Cell parameters from 9001 reflections
a = 23.8174 (4) Å	θ = 2.7–30.5°
b = 10.9141 (2) Å	µ = 0.75 mm−1
c = 7.4645 (1) Å	T = 100 K
V = 1940.36 (5) Å3	Blade, colorless
Z = 4	0.33 × 0.27 × 0.10 mm

Bruker APEXII CCD diffractometer	2157 independent reflections
Radiation source: fine-focus sealed tube	2149 reflections with I > 2σ(I)
graphite	Rint = 0.015
φ and ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −30→30
Tmin = 0.791, Tmax = 0.929	k = −13→13
8594 measured reflections	l = −9→9

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)] = 0.015	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.042	w = 1/[σ2(Fo2) + (0.0201P)2 + 1.0371P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
2157 reflections	Δρmax = 0.26 e Å−3
145 parameters	Δρmin = −0.23 e Å−3
7 restraints	Absolute structure: Flack (1983), 985 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (3)

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
K1	0.5000	0.39021 (4)	0.59975 (5)	0.01535 (8)
K2	0.5000	0.05477 (3)	0.26065 (6)	0.01442 (8)
S1	0.404982 (11)	0.35192 (2)	0.25404 (4)	0.01158 (7)
O1	0.42926 (4)	0.47094 (8)	0.30427 (12)	0.01535 (19)
O2	0.42708 (4)	0.25122 (8)	0.36386 (12)	0.01634 (19)
N1	0.41122 (4)	0.31915 (11)	0.05418 (15)	0.0147 (2)
H1	0.4057 (7)	0.3869 (13)	−0.007 (2)	0.018*
N2	0.15806 (5)	0.38097 (11)	0.38621 (15)	0.0148 (2)
H2A	0.1423 (6)	0.3121 (13)	0.430 (2)	0.018*
H2B	0.1402 (6)	0.4057 (14)	0.285 (2)	0.018*
C1	0.33256 (5)	0.36379 (11)	0.30816 (17)	0.0124 (2)
C2	0.30175 (5)	0.46150 (10)	0.23864 (18)	0.0138 (2)
H2	0.3202	0.5243	0.1732	0.017*
C3	0.24417 (5)	0.46705 (10)	0.26498 (19)	0.0134 (2)
H3	0.2234	0.5342	0.2183	0.016*
C4	0.21636 (5)	0.37450 (11)	0.35982 (16)	0.0126 (2)
C5	0.24773 (5)	0.27905 (12)	0.43346 (18)	0.0144 (2)
H5	0.2295	0.2175	0.5023	0.017*
C6	0.30546 (5)	0.27342 (11)	0.40674 (17)	0.0138 (2)
H6	0.3265	0.2075	0.4561	0.017*
O3	0.58605 (4)	−0.04452 (9)	0.07181 (13)	0.0173 (2)
H3A	0.6103 (6)	0.0020 (18)	0.023 (3)	0.026*
H3B	0.5880 (8)	−0.1110 (15)	0.019 (3)	0.026*
O4	0.5000	0.18900 (13)	0.8893 (2)	0.0207 (3)
H4	0.4747 (6)	0.2267 (16)	0.929 (3)	0.031*

	U11	U22	U33	U12	U13	U23
K1	0.01301 (16)	0.01830 (18)	0.01474 (17)	0.000	0.000	−0.00331 (15)
K2	0.01360 (16)	0.01577 (17)	0.01391 (16)	0.000	0.000	−0.00172 (17)
S1	0.01032 (12)	0.01235 (13)	0.01206 (13)	−0.00085 (9)	0.00042 (13)	0.00013 (13)
O1	0.0144 (4)	0.0149 (4)	0.0168 (5)	−0.0035 (3)	0.0009 (3)	−0.0022 (3)
O2	0.0134 (4)	0.0169 (4)	0.0188 (5)	0.0009 (3)	−0.0002 (4)	0.0048 (4)
N1	0.0158 (5)	0.0161 (5)	0.0123 (5)	−0.0002 (4)	0.0024 (4)	−0.0005 (4)
N2	0.0118 (5)	0.0178 (5)	0.0148 (5)	0.0007 (4)	0.0004 (4)	0.0019 (4)
C1	0.0113 (6)	0.0142 (5)	0.0118 (5)	−0.0010 (5)	0.0009 (4)	−0.0027 (4)
C2	0.0163 (5)	0.0129 (5)	0.0120 (6)	−0.0015 (4)	0.0019 (5)	0.0017 (5)
C3	0.0157 (5)	0.0123 (5)	0.0121 (5)	0.0017 (4)	−0.0004 (5)	0.0008 (5)
C4	0.0121 (6)	0.0156 (6)	0.0102 (6)	−0.0001 (5)	0.0009 (4)	−0.0028 (5)
C5	0.0161 (6)	0.0136 (5)	0.0136 (5)	−0.0019 (5)	0.0017 (5)	0.0016 (5)
C6	0.0139 (6)	0.0134 (5)	0.0142 (6)	0.0010 (4)	−0.0007 (5)	0.0016 (5)
O3	0.0177 (4)	0.0155 (4)	0.0187 (5)	−0.0009 (3)	0.0033 (4)	−0.0010 (4)
O4	0.0135 (7)	0.0205 (7)	0.0280 (8)	0.000	0.000	−0.0097 (6)

K1—O1i	2.7325 (9)	N1—H1	0.878 (14)
K1—O1ii	2.7325 (9)	N2—C4	1.4044 (16)
K1—O2iii	2.9014 (10)	N2—H2A	0.903 (13)
K1—O2	2.9014 (10)	N2—H2B	0.906 (14)
K1—O1	2.9121 (10)	C1—C6	1.3895 (17)
K1—O1iii	2.9121 (10)	C1—C2	1.3947 (17)
K1—O4	3.0810 (16)	C2—C3	1.3868 (17)
K2—O3	2.7133 (10)	C2—H2	0.9500
K2—O3iii	2.7133 (10)	C3—C4	1.4000 (17)
K2—O4iv	2.8285 (15)	C3—H3	0.9500
K2—O2iii	2.8648 (10)	C4—C5	1.3948 (18)
K2—O2	2.8648 (10)	C5—C6	1.3908 (17)
K2—O3v	3.0996 (10)	C5—H5	0.9500
K2—O3vi	3.0996 (10)	C6—H6	0.9500
K2—O4vii	3.1355 (17)	O3—K2iv	3.0996 (10)
S1—O2	1.4686 (9)	O3—H3A	0.852 (15)
S1—O1	1.4705 (9)	O3—H3B	0.828 (15)
S1—N1	1.5413 (12)	O4—K2vi	2.8284 (15)
S1—C1	1.7763 (13)	O4—K2ix	3.1355 (17)
O1—K1viii	2.7324 (9)	O4—H4	0.787 (13)
O1i—K1—O1ii	76.15 (4)	O3vi—K2—O4vii	132.79 (2)
O1i—K1—O2iii	105.06 (3)	O2—S1—O1	112.21 (6)
O1ii—K1—O2iii	176.54 (3)	O2—S1—N1	109.40 (6)
O1i—K1—O2	176.54 (3)	O1—S1—N1	114.44 (6)
O1ii—K1—O2	105.06 (3)	O2—S1—C1	106.00 (6)
O2iii—K1—O2	73.54 (4)	O1—S1—C1	105.03 (6)
O1i—K1—O1	127.75 (2)	N1—S1—C1	109.31 (6)
O1ii—K1—O1	84.18 (2)	S1—O1—K1viii	126.15 (5)
O2iii—K1—O1	92.57 (3)	S1—O1—K1	98.82 (4)
O2—K1—O1	49.62 (3)	K1viii—O1—K1	103.54 (3)
O1i—K1—O1iii	84.18 (2)	S1—O2—K2	128.84 (5)
O1ii—K1—O1iii	127.75 (2)	S1—O2—K1	99.32 (5)
O2iii—K1—O1iii	49.62 (3)	K2—O2—K1	101.04 (3)
O2—K1—O1iii	92.58 (3)	S1—N1—H1	106.9 (11)
O1—K1—O1iii	70.71 (4)	C4—N2—H2A	114.8 (10)
O1i—K1—O4	90.20 (3)	C4—N2—H2B	111.3 (10)
O1ii—K1—O4	90.20 (3)	H2A—N2—H2B	110.9 (15)
O2iii—K1—O4	93.04 (3)	C6—C1—C2	119.69 (11)
O2—K1—O4	93.04 (3)	C6—C1—S1	121.31 (10)
O1—K1—O4	138.32 (2)	C2—C1—S1	118.83 (10)
O1iii—K1—O4	138.32 (2)	C3—C2—C1	120.07 (11)
O3—K2—O3iii	98.12 (4)	C3—C2—H2	120.0
O3—K2—O4iv	78.50 (3)	C1—C2—H2	120.0
O3iii—K2—O4iv	78.50 (3)	C2—C3—C4	120.53 (11)
O3—K2—O2iii	88.89 (3)	C2—C3—H3	119.7
O3iii—K2—O2iii	153.71 (3)	C4—C3—H3	119.7
O4iv—K2—O2iii	127.79 (3)	C5—C4—C3	119.00 (11)
O3—K2—O2	153.71 (3)	C5—C4—N2	120.79 (11)
O3iii—K2—O2	88.89 (3)	C3—C4—N2	120.15 (11)
O4iv—K2—O2	127.78 (3)	C6—C5—C4	120.40 (12)
O2iii—K2—O2	74.64 (4)	C6—C5—H5	119.8
O3—K2—O3v	82.84 (3)	C4—C5—H5	119.8
O3iii—K2—O3v	150.97 (2)	C1—C6—C5	120.25 (11)
O4iv—K2—O3v	73.24 (3)	C1—C6—H6	119.9
O2iii—K2—O3v	54.88 (3)	C5—C6—H6	119.9
O2—K2—O3v	103.08 (3)	K2—O3—K2iv	84.51 (3)
O3—K2—O3vi	150.97 (2)	K2—O3—H3A	119.9 (14)
O3iii—K2—O3vi	82.84 (3)	K2iv—O3—H3A	98.5 (13)
O4iv—K2—O3vi	73.24 (3)	K2—O3—H3B	129.9 (13)
O2iii—K2—O3vi	103.08 (3)	K2iv—O3—H3B	69.3 (13)
O2—K2—O3vi	54.87 (3)	H3A—O3—H3B	106 (2)
O3v—K2—O3vi	82.79 (4)	K2vi—O4—K1	115.62 (5)
O3—K2—O4vii	74.17 (3)	K2vi—O4—K2ix	81.99 (4)
O3iii—K2—O4vii	74.17 (3)	K1—O4—K2ix	162.39 (5)
O4iv—K2—O4vii	137.70 (5)	K2vi—O4—H4	128.2 (13)
O2iii—K2—O4vii	83.57 (3)	K1—O4—H4	83.7 (15)
O2—K2—O4vii	83.57 (3)	K2ix—O4—H4	85.1 (16)
O3v—K2—O4vii	132.79 (2)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1x	0.88 (1)	2.17 (1)	2.9854 (15)	154.(2)
N2—H2A···N1xi	0.90 (1)	2.13 (1)	3.0109 (16)	166.(1)
N2—H2B···O3xii	0.91 (1)	2.12 (1)	3.0183 (15)	171.(1)
O3—H3A···N2xiii	0.85 (2)	1.99 (2)	2.8366 (15)	172.(2)
O3—H3B···O2iv	0.83 (2)	1.95 (2)	2.7561 (13)	164.(2)
O4—H4···N1ix	0.79 (1)	2.05 (1)	2.8291 (14)	175 (2)
C2—H2···Cg1x	0.95	2.98	3.5872 (14)	123
C5—H5···Cg1xi	0.95	2.66	3.4531 (14)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88 (1)	2.17 (1)	2.9854 (15)	154 (2)
N2—H2A⋯N1ii	0.90 (1)	2.13 (1)	3.0109 (16)	166 (1)
N2—H2B⋯O3iii	0.91 (1)	2.12 (1)	3.0183 (15)	171 (1)
O3—H3A⋯N2iv	0.85 (2)	1.99 (2)	2.8366 (15)	172 (2)
O3—H3B⋯O2v	0.83 (2)	1.95 (2)	2.7561 (13)	164 (2)
O4—H4⋯N1vi	0.79 (1)	2.05 (1)	2.8291 (14)	175 (2)
C2—H2⋯Cg1i	0.95	2.98	3.5872 (14)	123
C5—H5⋯Cg1ii	0.95	2.66	3.4531 (14)	141

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