Dipotassium disulfanilamidate trihydrate

How, F.N.-F.; Rahima, Z.A.; Khaledi, H.; Mohd Ali, H.

doi:10.1107/S1600536811026791

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1071

doi:10.1107/S1600536811026791

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Dipotassium disulfanilamidate trihydrate

Fiona N.-F How,^a Z. A. Rahima,^a Hamid Khaledi ^b ^* and Hapipah Mohd Ali ^b

^aDepartment of Biomedical Sciences, Kulliyah of Science, IIUM Kuantan, 25200 Kuantan, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 3 July 2011; accepted 5 July 2011; online 9 July 2011)

The asymmetric unit of the title compound, 2K⁺·2C₆H₇N₂O₂S⁻·3H₂O, consists of two potassium cations located on mirror planes, one sulfanilamidate anion in a general position and one and a half molecules 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 molecule, 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 interactions. 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_r = 474.64
Orthorhombic, C m c 2₁
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[F² > 2σ(F²)] = 0.015
wR(F²) = 0.042
S = 1.11
2157 reflections
145 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 985 Friedel pairs
Flack parameter: 0.04 (3)

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⋯N2^iv	0.85 (2)	1.99 (2)	2.8366 (15)	172 (2)
O3—H3B⋯O2^v	0.83 (2)	1.95 (2)	2.7561 (13)	164 (2)
O4—H4⋯N1^vi	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) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) $[-x+1, -y, z-{\script{1\over 2}}]$ ; (vi) x, y, z+1.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811026791/om2446sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811026791/om2446Isup3.cml

checkCIF report

Comment top

The title potassium salt (Fig. 1) was obtained through the deprotonation of sulfanilamide by KOH. The structure contains two types of potassium cation, one of which, K1, is hepta-coordinated by six sulfonyl O atoms and one water molecule while the other one, K2, is octa-coordinated by six water O atoms and two sulfonyl O atoms. Both potassium atoms and one water oxygen atom, O4, are placed on a mirror plane.

The bond distance of S—N [1.5410 (12) Å] implies its double bond character and is slightly shorter than the observed values (~ 1.58 Å) in similar potassium salts (Gowda et al., 2011; Moers et al., 2001), but comparable with the bond length reported for sodium sulfanilamide (Moreno & Alleaume, 1968). The S1—O1 and S1—O2 distances of 1.4686 (9) and 1.4705 (9) Å attest to delocalization of the negative charge over the O—S—O fragment. These values are similar to the corresponding values in sodium sulfanilamide (1.45–1.46 Å).

In the crystal, coordination polymeric layers are formed in the bc plane (Fig. 2). The two dimensional structure is supplemented by N—H···O, O—H···O, O—H···N and C—H···π interactions (Table 1). The layers are further linked into a three dimensional network via N—H···O, N—H···N and O—H···N hydrogen bonds (Fig. 3)

Related literature top

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 top

Sulfanilamide (2 g) in ethanol (30 ml) was mixed with an equimolar amount of KOH in 90% ethanol (10 ml). The solution was then refluxed for 2 hr and left to cool down at room temperature. The colorless crystals of the the potassium salt were obtained within a day.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot of the title compound at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Symmetry code: i = -x + 1, y, z; ii = x, -y + 1, z + 1/2; iii = -x + 1, -y + 1, z + 1/2; iv = x, -y, z + 1/2; v = -x + 1, -y, z + 1/2; vi = x, y, z - 1; vii = -x + 1, -y, z - 1/2.
	Fig. 2. Packing view looking down the crystallographic α axis showing the two dimensional coordination polymer netwrok.
	Fig. 3. Packing view looking down the crystallographic c axis. H-bonds are shown as red dashed lines.

Dipotassium disulfanilamidate trihydrate top

Crystal data top

2K⁺·2C₆H₇N₂O₂S⁻·3H₂O	F(000) = 984
M_r = 474.64	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0201P)² + 1.0371P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
2157 reflections	Δρ_max = 0.26 e Å⁻³
145 parameters	Δρ_min = −0.23 e Å⁻³
7 restraints	Absolute structure: Flack (1983), 985 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (3)

Crystal data top

2K⁺·2C₆H₇N₂O₂S⁻·3H₂O	V = 1940.36 (5) Å³
M_r = 474.64	Z = 4
Orthorhombic, Cmc2₁	Mo Kα radiation
a = 23.8174 (4) Å	µ = 0.75 mm⁻¹
b = 10.9141 (2) Å	T = 100 K
c = 7.4645 (1) Å	0.33 × 0.27 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	2157 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2149 reflections with I > 2σ(I)
T_min = 0.791, T_max = 0.929	R_int = 0.015
8594 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.015	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.042	Δρ_max = 0.26 e Å⁻³
S = 1.11	Δρ_min = −0.23 e Å⁻³
2157 reflections	Absolute structure: Flack (1983), 985 Friedel pairs
145 parameters	Absolute structure parameter: 0.04 (3)
7 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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—O4^iv	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—O3^v	3.0996 (10)	C5—H5	0.9500
K2—O3^vi	3.0996 (10)	C6—H6	0.9500
K2—O4^vii	3.1355 (17)	O3—K2^iv	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—K2^vi	2.8284 (15)
S1—C1	1.7763 (13)	O4—K2^ix	3.1355 (17)
O1—K1^viii	2.7324 (9)	O4—H4	0.787 (13)

O1ⁱ—K1—O1ⁱⁱ	76.15 (4)	O3^vi—K2—O4^vii	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—K1^viii	126.15 (5)
O2ⁱⁱⁱ—K1—O1	92.57 (3)	S1—O1—K1	98.82 (4)
O2—K1—O1	49.62 (3)	K1^viii—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—O4^iv	78.50 (3)	C1—C2—H2	120.0
O3ⁱⁱⁱ—K2—O4^iv	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
O4^iv—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)
O4^iv—K2—O2	127.78 (3)	C6—C5—C4	120.40 (12)
O2ⁱⁱⁱ—K2—O2	74.64 (4)	C6—C5—H5	119.8
O3—K2—O3^v	82.84 (3)	C4—C5—H5	119.8
O3ⁱⁱⁱ—K2—O3^v	150.97 (2)	C1—C6—C5	120.25 (11)
O4^iv—K2—O3^v	73.24 (3)	C1—C6—H6	119.9
O2ⁱⁱⁱ—K2—O3^v	54.88 (3)	C5—C6—H6	119.9
O2—K2—O3^v	103.08 (3)	K2—O3—K2^iv	84.51 (3)
O3—K2—O3^vi	150.97 (2)	K2—O3—H3A	119.9 (14)
O3ⁱⁱⁱ—K2—O3^vi	82.84 (3)	K2^iv—O3—H3A	98.5 (13)
O4^iv—K2—O3^vi	73.24 (3)	K2—O3—H3B	129.9 (13)
O2ⁱⁱⁱ—K2—O3^vi	103.08 (3)	K2^iv—O3—H3B	69.3 (13)
O2—K2—O3^vi	54.87 (3)	H3A—O3—H3B	106 (2)
O3^v—K2—O3^vi	82.79 (4)	K2^vi—O4—K1	115.62 (5)
O3—K2—O4^vii	74.17 (3)	K2^vi—O4—K2^ix	81.99 (4)
O3ⁱⁱⁱ—K2—O4^vii	74.17 (3)	K1—O4—K2^ix	162.39 (5)
O4^iv—K2—O4^vii	137.70 (5)	K2^vi—O4—H4	128.2 (13)
O2ⁱⁱⁱ—K2—O4^vii	83.57 (3)	K1—O4—H4	83.7 (15)
O2—K2—O4^vii	83.57 (3)	K2^ix—O4—H4	85.1 (16)
O3^v—K2—O4^vii	132.79 (2)

Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) x, −y+1, z+1/2; (iii) −x+1, y, z; (iv) −x+1, −y, z−1/2; (v) x, −y, z+1/2; (vi) −x+1, −y, z+1/2; (vii) x, y, z−1; (viii) −x+1, −y+1, z−1/2; (ix) x, y, z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^x	0.88 (1)	2.17 (1)	2.9854 (15)	154 (2)
N2—H2A···N1^xi	0.90 (1)	2.13 (1)	3.0109 (16)	166 (1)
N2—H2B···O3^xii	0.91 (1)	2.12 (1)	3.0183 (15)	171 (1)
O3—H3A···N2^xiii	0.85 (2)	1.99 (2)	2.8366 (15)	172 (2)
O3—H3B···O2^iv	0.83 (2)	1.95 (2)	2.7561 (13)	164 (2)
O4—H4···N1^ix	0.79 (1)	2.05 (1)	2.8291 (14)	175 (2)
C2—H2···Cg1^x	0.95	2.98	3.5872 (14)	123
C5—H5···Cg1^xi	0.95	2.66	3.4531 (14)	141

Symmetry codes: (iv) −x+1, −y, z−1/2; (ix) x, y, z+1; (x) x, −y+1, z−1/2; (xi) −x+1/2, −y+1/2, z+1/2; (xii) x−1/2, y+1/2, z; (xiii) x+1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	2K⁺·2C₆H₇N₂O₂S⁻·3H₂O
M_r	474.64
Crystal system, space group	Orthorhombic, Cmc2₁
Temperature (K)	100
a, b, c (Å)	23.8174 (4), 10.9141 (2), 7.4645 (1)
V (Å³)	1940.36 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.33 × 0.27 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.791, 0.929
No. of measured, independent and observed [I > 2σ(I)] reflections	8594, 2157, 2149
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.015, 0.042, 1.11
No. of reflections	2157
No. of parameters	145
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.23
Absolute structure	Flack (1983), 985 Friedel pairs
Absolute structure parameter	0.04 (3)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.878 (14)	2.171 (14)	2.9854 (15)	154.1 (15)
N2—H2A···N1ⁱⁱ	0.903 (13)	2.129 (14)	3.0109 (16)	165.5 (14)
N2—H2B···O3ⁱⁱⁱ	0.906 (14)	2.121 (14)	3.0183 (15)	170.5 (14)
O3—H3A···N2^iv	0.852 (15)	1.991 (16)	2.8366 (15)	171.9 (18)
O3—H3B···O2^v	0.828 (15)	1.951 (15)	2.7561 (13)	163.8 (18)
O4—H4···N1^vi	0.787 (13)	2.045 (14)	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) x, −y+1, z−1/2; (ii) −x+1/2, −y+1/2, z+1/2; (iii) x−1/2, y+1/2, z; (iv) x+1/2, −y+1/2, z−1/2; (v) −x+1, −y, z−1/2; (vi) x, y, z+1.

Acknowledgements

IIUM is acknowledged for funding this study (Endowment fund A No: EDW A10–150-0697).

References

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Volume 67| Part 8| August 2011| Page m1071

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