4-Sulfamoylanilinium perchlorate

Anitha, R.; Athimoolam, S.; Gunasekaran, M.; Sridhar, B.

doi:10.1107/S1600536813017972

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1236

doi:10.1107/S1600536813017972

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4-Sulfamoylanilinium perchlorate

R. Anitha,^a S. Athimoolam,^b M. Gunasekaran ^a ^* and B. Sridhar ^c

^aDepartment of Physics, Regional centre of Anna University, Tirunelveli Region, Tirunelveli 627 007, India, ^bDepartment of Physics, University College of Engineering, Nagercoil, Anna University, Tirunelveli Region, Nagercoil 629 004, India, and ^cLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 607, India
^*Correspondence e-mail: physics.autt@gmail.com

(Received 8 June 2013; accepted 29 June 2013; online 10 July 2013)

In the crystal of the title salt, C₆H₉N₂O₂S⁺·ClO₄⁻, the components are linked by N—H⋯O hydrogen bonds, forming a three-dimensional network. The cations are connected along a and b axes, leading to linear and zigzag C(3) and C(8) chain motifs, respectively. A cation–anion interaction along the c axis leads to a C₂²(12) chain motif. R₃³(18) and R₃³(20) ring motifs are observed as cation–anion-type interactions. These hydrogen-bonding ring and chain motifs are localized at z = 0 or 1, leading to alternate hydrophilic and hydrophobic regions along the c axis as a result of the stacking of anions and the aromatic cationic parts.

Related literature

For the first use of sulfanilamide, see: Buttle et al. (1936 ). For related structures, see: Ravikumar et al. (2013 ); Pandiarajan et al. (2011 ); Topacli & Kesimli (2001 ). For graph-set motifs, see Etter et al. (1990 ).

Experimental

Crystal data

C₆H₉N₂O₂S⁺·ClO₄⁻
M_r = 272.66
Monoclinic, P 2₁
a = 4.9158 (10) Å
b = 10.514 (2) Å
c = 9.814 (2) Å
β = 93.716 (3)°
V = 506.15 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.60 mm⁻¹
T = 293 K
0.24 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
5796 measured reflections
2367 independent reflections
2361 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.061
S = 1.08
2367 reflections
166 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ), 1287 Friedel pairs
Flack parameter: 0.00 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.88 (1)	2.12 (1)	2.953 (2)	160 (3)
N1—H1B⋯O6ⁱⁱ	0.88 (3)	2.30 (3)	3.086 (2)	149 (2)
N2—H2A⋯O5ⁱ	0.88 (1)	2.19 (1)	3.044 (2)	164 (3)
N2—H2B⋯O2ⁱⁱⁱ	0.88 (1)	2.16 (2)	2.876 (2)	139 (2)
N2—H2C⋯O4^iv	0.88 (1)	2.30 (2)	2.858 (2)	122 (2)
N2—H2C⋯O5	0.88 (1)	2.37 (2)	3.058 (2)	136 (2)
Symmetry codes: (i) x+1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x+2, y+{\script{1\over 2}}, -z+1]$ ; (iv) $[-x+1, y+{\script{1\over 2}}, -z]$ .

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; molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL/PC.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813017972/ng5332sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813017972/ng5332Isup2.hkl

checkCIF report

Comment top

Sulfa drugs, mostly the derivatives of sulfanilamide, have been an integral part of our medical history. They were the first effective chemotherapeutic agents to be widely used for the treatment of bacterial infection in humans and animals (Topacli & Kesimli, 2001). The uses of Sulfanilamide, was started during 1936 (Buttle et al., 1936) and the grandparent of the sulfonamide family of drugs that are still in use today. The nitrate and sulfate complexes of sulfanilamide (Pandiarajan et al., 2011; Ravikumar et al., 2013) were already reported. In continuation of our interest on the sulfanilamide complexes, the synthesis of the title compound and its title structure,bis(4-sulfamoylanilinium) sulfate, is described here. In the title structure, a protonated sulfomylanilinium cation and a perchlorate anion constitute the asymmetric part (Fig. 1). The protonation on the one of N sites is confirmed from C—N bond distance. The geometrical parameters of the cation are in agreement with the reported sulfomylanilinium structures in 4-sulfomylanilinium nitrate (Pandiarajan et al., 2011) and Bis(4-sulfomylanilinium) sulfate (Ravikumar et al., 2013).

The crystal structure is stabilized through intricate three dimensional hydrogen bonding network formed through N—H···O interactions (Table 1; Fig. 2). All the hydrogen atoms attached to both the nitrogen atoms of the cation is involved in the hydrogen bonding interactions as donors. All the oxygen atoms in the cation and anion, except the O3 atom present in the anion, are acting as acceptor atoms and involved in the hydrogen bonding interactions. One of the N—H···O hydrogen bonds is observed to be bifurcated hydrogen bond, with one donor hydrogen (Table 1): N2—H3N···O4 (-x + 1, y + 1/2, -z) and N2—H3N···O5. Among the hydrogen bonds, two are cation-cation type and other four hydrogen bonds are cation-anion type. In the cation-cation type, N1—H2N···O1(1 + x, y, z) is making a chain C(3) motif extending along a-axis of the unit cell. Another N2—H5N···O2(2 - x, 1/2 + y, 1 - z) hydrogen bond is connecting the cations along b-axis of the unit cell through zigzag chain C(8) motifs. Thus cations are connected directly only along a & b-axes. Whereas along c-axis the interactions are cation-anion type, i.e., the cations and anions are connected through N1—H1N···O6(-x + 1, y + 1/2, -z + 1) and N2—H3N···O4(-x + 1, y + 1/2, -z) hydrogen bonds leading to chain C₂2⁽12) motif.

Further, cations and anions are connected through N1—H2N···O1(1 + x, y, z), N2—H3N···O5 and N2—H4N···O5(1 + x, y, z) leading to a ring R₃³(18) motifs. Another ring R₃³(20) motif is formed through N1—H1N···O6(-x + 1, y + 1/2, -z + 1), N2—H4N···O5(1 + x, y, z) and N2—H5N···O2(-x + 2, y + 1/2, -z + 1) hydrogen bonds. These ring R₃³(20) motifs are arranged adjacently and making a chain C₃³(10) motif extending along b-axis of the unit cell. These hydrogen bonding ring and chain motifs are localized at z = 0 or z = 1 leading to alternate hydrophilic and hydrophobic regions along c axis as a result of the stacking of anions and the aromatic cationic parts.

Related literature top

For related structures, see Buttle et al. (1936); Ravikumar et al. (2013); Pandiarajan et al. (2011); Topacli & Kesimli (2001). For graph-set motifs, see Etter et al. (1990).

Experimental top

The synthesis of the title compound was carried out by heating of the mixture of sulphanilamide (1.7 g) and perchloric acid (0.5 ml of 98%)in water with the stoichiometric ratio of 1:1 (at 60°C) under reflux for 1 h. Colourless needle type crystals of the title compound suitable for single-crystal X-ray analysis with the approximate size of 1.8 cm τimes 0.6 cm τimes 0.4 cm were obtained by slow evaporation at room temperature. The measured sample was cut from a bigger crystal. Caution: Although no problems were encountered in this work, perchlorate compounds are potentially explosive. They should be prepared in small amounts and handled with care.

Computing details top

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

Figures top

	Fig. 1. The title molecule with the atom numbering scheme. The displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. Packing diagram of the title compound viewed down the aaxis. The H-bonds are shown as dashed lines.

4-Sulfomylanilinium perchlorate top

Crystal data top

C₆H₉N₂O₂S⁺·ClO₄⁻	F(000) = 280
M_r = 272.66	D_x = 1.789 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2412 reflections
a = 4.9158 (10) Å	θ = 2.5–24.7°
b = 10.514 (2) Å	µ = 0.60 mm⁻¹
c = 9.814 (2) Å	T = 293 K
β = 93.716 (3)°	Needle, colourless
V = 506.15 (18) Å³	0.24 × 0.16 × 0.12 mm
Z = 2

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2361 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 28.0°, θ_min = 2.1°
ω scans	h = −6→6
5796 measured reflections	k = −13→13
2367 independent reflections	l = −12→12

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.022	w = 1/[σ²(F_o²) + (0.0315P)² + 0.1129P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.061	(Δ/σ)_max = 0.001
S = 1.08	Δρ_max = 0.31 e Å⁻³
2367 reflections	Δρ_min = −0.26 e Å⁻³
166 parameters	Extinction correction: SHELXTL/PC (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
5 restraints	Extinction coefficient: 0.189 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1287 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.00 (4)

Crystal data top

C₆H₉N₂O₂S⁺·ClO₄⁻	V = 506.15 (18) Å³
M_r = 272.66	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 4.9158 (10) Å	µ = 0.60 mm⁻¹
b = 10.514 (2) Å	T = 293 K
c = 9.814 (2) Å	0.24 × 0.16 × 0.12 mm
β = 93.716 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2361 reflections with I > 2σ(I)
5796 measured reflections	R_int = 0.023
2367 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.061	Δρ_max = 0.31 e Å⁻³
S = 1.08	Δρ_min = −0.26 e Å⁻³
2367 reflections	Absolute structure: Flack (1983), 1287 Friedel pairs
166 parameters	Absolute structure parameter: 0.00 (4)
5 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
C1	0.8057 (3)	0.53210 (15)	0.53535 (15)	0.0244 (3)
C2	1.0030 (3)	0.46394 (16)	0.47189 (16)	0.0295 (3)
H2	1.0919	0.3964	0.5169	0.035*
C3	1.0672 (3)	0.49695 (19)	0.34095 (16)	0.0293 (3)
H3	1.1998	0.4523	0.2973	0.035*
C4	0.9310 (3)	0.59698 (15)	0.27676 (15)	0.0235 (3)
C5	0.7316 (3)	0.66524 (16)	0.33789 (17)	0.0281 (3)
H5	0.6419	0.7320	0.2920	0.034*
C6	0.6676 (3)	0.63237 (17)	0.46891 (17)	0.0294 (3)
H6	0.5338	0.6768	0.5119	0.035*
N1	0.9084 (3)	0.58560 (16)	0.80644 (15)	0.0315 (3)
N2	0.9994 (3)	0.63135 (15)	0.13833 (15)	0.0279 (3)
O1	0.4527 (2)	0.51671 (14)	0.71892 (14)	0.0380 (3)
O2	0.8370 (3)	0.36510 (13)	0.72799 (14)	0.0385 (3)
H1A	1.0834 (17)	0.578 (3)	0.797 (3)	0.070 (9)*
H1B	0.847 (5)	0.665 (3)	0.803 (3)	0.047 (7)*
H2A	1.120 (4)	0.584 (2)	0.100 (3)	0.055 (7)*
H2B	1.052 (5)	0.7108 (9)	0.134 (3)	0.053 (8)*
H2C	0.863 (4)	0.617 (3)	0.078 (2)	0.048 (7)*
Cl1	0.58672 (7)	0.34769 (3)	0.07752 (4)	0.02621 (11)
O3	0.8773 (2)	0.34793 (17)	0.06980 (15)	0.0409 (3)
O4	0.4686 (3)	0.26701 (16)	−0.02835 (16)	0.0477 (4)
O5	0.4874 (3)	0.47611 (13)	0.05900 (15)	0.0399 (3)
O6	0.5169 (3)	0.30181 (14)	0.20823 (15)	0.0445 (3)
S1	0.73500 (7)	0.49156 (3)	0.70441 (4)	0.02528 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0265 (7)	0.0256 (7)	0.0217 (7)	−0.0006 (6)	0.0055 (5)	0.0017 (5)
C2	0.0328 (7)	0.0291 (8)	0.0268 (7)	0.0085 (6)	0.0034 (6)	0.0022 (6)
C3	0.0318 (7)	0.0310 (8)	0.0258 (7)	0.0071 (7)	0.0066 (5)	−0.0021 (6)
C4	0.0246 (6)	0.0244 (7)	0.0217 (6)	−0.0033 (5)	0.0026 (5)	0.0002 (5)
C5	0.0295 (8)	0.0260 (8)	0.0289 (7)	0.0051 (6)	0.0039 (6)	0.0046 (6)
C6	0.0286 (7)	0.0294 (8)	0.0311 (8)	0.0067 (6)	0.0091 (6)	0.0020 (7)
N1	0.0303 (7)	0.0361 (8)	0.0285 (7)	0.0003 (6)	0.0048 (6)	−0.0044 (6)
N2	0.0309 (7)	0.0293 (7)	0.0239 (6)	−0.0016 (6)	0.0045 (5)	0.0020 (6)
O1	0.0264 (6)	0.0523 (9)	0.0362 (6)	−0.0018 (5)	0.0090 (5)	0.0027 (6)
O2	0.0532 (8)	0.0281 (7)	0.0355 (6)	0.0052 (6)	0.0131 (5)	0.0080 (5)
Cl1	0.02693 (18)	0.02327 (17)	0.02901 (19)	−0.00278 (13)	0.00626 (12)	−0.00363 (14)
O3	0.0255 (6)	0.0483 (7)	0.0495 (7)	0.0003 (6)	0.0069 (5)	−0.0073 (7)
O4	0.0489 (8)	0.0478 (8)	0.0466 (9)	−0.0168 (7)	0.0033 (7)	−0.0193 (7)
O5	0.0413 (7)	0.0271 (7)	0.0522 (8)	0.0048 (6)	0.0092 (6)	0.0027 (6)
O6	0.0560 (8)	0.0424 (8)	0.0366 (7)	−0.0042 (6)	0.0155 (6)	0.0060 (6)
S1	0.02663 (18)	0.02599 (19)	0.02388 (17)	0.00010 (14)	0.00668 (12)	0.00191 (14)

Geometric parameters (Å, º) top

C1—C2	1.386 (2)	N1—S1	1.6113 (16)
C1—C6	1.393 (2)	N1—H1A	0.875 (5)
C1—S1	1.7692 (15)	N1—H1B	0.88 (3)
C2—C3	1.387 (2)	N2—H2A	0.877 (5)
C2—H2	0.9300	N2—H2B	0.876 (5)
C3—C4	1.377 (2)	N2—H2C	0.876 (5)
C3—H3	0.9300	O1—S1	1.4289 (13)
C4—C5	1.383 (2)	O2—S1	1.4345 (14)
C4—N2	1.466 (2)	Cl1—O6	1.4328 (14)
C5—C6	1.387 (2)	Cl1—O4	1.4345 (14)
C5—H5	0.9300	Cl1—O3	1.4355 (12)
C6—H6	0.9300	Cl1—O5	1.4432 (14)

C2—C1—C6	121.01 (14)	H1A—N1—H1B	115 (3)
C2—C1—S1	118.86 (12)	C4—N2—H2A	117.2 (19)
C6—C1—S1	120.12 (12)	C4—N2—H2B	111.4 (18)
C1—C2—C3	119.67 (15)	H2A—N2—H2B	108 (3)
C1—C2—H2	120.2	C4—N2—H2C	111.9 (18)
C3—C2—H2	120.2	H2A—N2—H2C	97 (3)
C4—C3—C2	118.80 (15)	H2B—N2—H2C	110 (3)
C4—C3—H3	120.6	O6—Cl1—O4	109.89 (10)
C2—C3—H3	120.6	O6—Cl1—O3	110.16 (9)
C3—C4—C5	122.36 (15)	O4—Cl1—O3	108.68 (9)
C3—C4—N2	118.57 (14)	O6—Cl1—O5	109.20 (9)
C5—C4—N2	119.06 (14)	O4—Cl1—O5	110.13 (10)
C4—C5—C6	118.85 (14)	O3—Cl1—O5	108.75 (9)
C4—C5—H5	120.6	O1—S1—O2	119.15 (9)
C6—C5—H5	120.6	O1—S1—N1	107.62 (8)
C5—C6—C1	119.31 (14)	O2—S1—N1	107.65 (9)
C5—C6—H6	120.3	O1—S1—C1	107.46 (7)
C1—C6—H6	120.3	O2—S1—C1	106.66 (7)
S1—N1—H1A	111 (2)	N1—S1—C1	107.86 (8)
S1—N1—H1B	112.7 (17)

C6—C1—C2—C3	0.9 (3)	C2—C1—C6—C5	−0.8 (2)
S1—C1—C2—C3	−177.99 (13)	S1—C1—C6—C5	178.07 (13)
C1—C2—C3—C4	−0.3 (3)	C2—C1—S1—O1	−147.96 (13)
C2—C3—C4—C5	−0.3 (3)	C6—C1—S1—O1	33.10 (16)
C2—C3—C4—N2	−179.92 (15)	C2—C1—S1—O2	−19.12 (16)
C3—C4—C5—C6	0.4 (2)	C6—C1—S1—O2	161.93 (14)
N2—C4—C5—C6	−179.99 (15)	C2—C1—S1—N1	96.28 (15)
C4—C5—C6—C1	0.2 (2)	C6—C1—S1—N1	−82.67 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.88 (1)	2.12 (1)	2.953 (2)	160 (3)
N1—H1B···O6ⁱⁱ	0.88 (3)	2.30 (3)	3.086 (2)	149 (2)
N2—H2A···O5ⁱ	0.88 (1)	2.19 (1)	3.044 (2)	164 (3)
N2—H2B···O2ⁱⁱⁱ	0.88 (1)	2.16 (2)	2.876 (2)	139 (2)
N2—H2C···O4^iv	0.88 (1)	2.30 (2)	2.858 (2)	122 (2)
N2—H2C···O5	0.88 (1)	2.37 (2)	3.058 (2)	136 (2)

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

Experimental details

Crystal data
Chemical formula	C₆H₉N₂O₂S⁺·ClO₄⁻
M_r	272.66
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	4.9158 (10), 10.514 (2), 9.814 (2)
β (°)	93.716 (3)
V (Å³)	506.15 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.60
Crystal size (mm)	0.24 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5796, 2367, 2361
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.061, 1.08
No. of reflections	2367
No. of parameters	166
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.26
Absolute structure	Flack (1983), 1287 Friedel pairs
Absolute structure parameter	0.00 (4)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL/PC (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.88 (1)	2.12 (1)	2.953 (2)	160 (3)
N1—H1B···O6ⁱⁱ	0.88 (3)	2.30 (3)	3.086 (2)	149 (2)
N2—H2A···O5ⁱ	0.88 (1)	2.19 (1)	3.044 (2)	164 (3)
N2—H2B···O2ⁱⁱⁱ	0.88 (1)	2.16 (2)	2.876 (2)	139 (2)
N2—H2C···O4^iv	0.88 (1)	2.30 (2)	2.858 (2)	122 (2)
N2—H2C···O5	0.88 (1)	2.37 (2)	3.058 (2)	136 (2)

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

Acknowledgements

SA is grateful to the Department of Science and Technology, SERB, for the financial support of this work in the form of the Fast-track Research Project scheme.

References

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