Bis(2-carboxy­anilinium) sulfate monohydrate

Akhtar, T.; Masih, K.; Tahir, M.N.; Tariq, M.I.; Iqbal, S.

doi:10.1107/S1600536810008913

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o819

doi:10.1107/S1600536810008913

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Bis(2-carboxyanilinium) sulfate monohydrate

Taslim Akhtar,^a Khawar Masih,^a M. Nawaz Tahir,^b ^* Muhammad Ilyas Tariq ^a and Shahid Iqbal ^a

^aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 8 March 2010; accepted 9 March 2010; online 13 March 2010)

In the title hydrated molecular salt, 2C₇H₈NO₂⁺·SO₄²⁻·H₂O, each cation in the asymmetric unit is stabilized by an intramolecular N—H⋯O hydrogen bond. The O atoms of the sulfate ion are disordered over two sets of sites with an occupancy ratio of 0.541 (13):0.459 (13), which possibly optimizes the acceptance of N—H⋯O hydrogen bonds from the cations. The crystal structure also features aromatic π–π stacking [centroid–centroid separation = 3.842 (2) Å] and a C—H⋯π interaction.

Related literature

For background to the properties and uses of aminobenzoic acids, see: Griss et al. (1984 ); Pedanova et al. (1984 ); Refaat (2010 ); Rogers & Clark (1973 ).

Experimental

Crystal data

2C₇H₈NO₂⁺·SO₄²⁻·H₂O
M_r = 390.36
Monoclinic, P 2₁ /n
a = 11.260 (5) Å
b = 10.542 (4) Å
c = 15.358 (5) Å
β = 109.737 (5)°
V = 1715.9 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.28 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.934, T_max = 0.955
12530 measured reflections
3748 independent reflections
2528 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.118
S = 1.02
3748 reflections
282 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O6Aⁱ	0.89	1.83	2.721 (6)	174
N1—H1B⋯O2	0.89	1.99	2.708 (3)	137
N1—H1B⋯O4ⁱⁱ	0.89	2.33	3.041 (3)	137
N1—H1C⋯O8Aⁱⁱⁱ	0.89	1.98	2.860 (11)	168
N2—H2A⋯O8A^iv	0.89	1.83	2.698 (12)	166
N2—H2B⋯O4	0.89	1.94	2.689 (3)	140
N2—H2B⋯O2ⁱⁱ	0.89	2.28	2.906 (3)	128
N2—H2C⋯O5Aⁱ	0.89	2.00	2.839 (6)	157
O1—H1⋯O9^v	0.82	1.75	2.557 (3)	168
O3—H3A⋯O7A^v	0.82	1.70	2.512 (13)	167
O9—H9A⋯O6A^vi	0.80 (3)	2.46 (3)	3.102 (8)	138 (3)
O9—H9A⋯O8A^vi	0.80 (3)	2.38 (4)	3.115 (11)	153 (3)
O9—H9B⋯O5A	0.86 (3)	1.96 (3)	2.792 (7)	161 (3)
C4—H4⋯Cg2^vii	0.93	2.75	3.600 (3)	153
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+1, -z+1; (iii) -x+1, -y, -z+1; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) -x+1, -y+1, -z+1; (vi) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810008913/hb5357sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810008913/hb5357Isup2.hkl

checkCIF report

Comment top

The salts of aminobenzoic acids have been reported as medicines as well as precursor for in the field of pharmaceutics (Griss et al., 1984). These are also useful for autoxidation of the fats forming free radicals, hence, in comparison to sulfated metal oxides, these can be used for production of biodiesel (Pedanova et al., 1984; Refaat, 2010). The structure of title compound (I, Fig. 1) is being reported here.

In the title compound (I) benzene rings A (C1–C6) and B (C8—C13) are of course planar with maximum r. m. s. deviations of 0.0025 and 0.0034 Å from the mean squares planes. The dihedral angle between A/B is 7.91 (13)°. The carboxylate groups C (O1/C7/O2) and D (O3/C14/O4) are oriented at dihedral angles of 11.94 (38)° and 10.86 (41)° with benzene rings A and B respectively. The O-atoms of SO₄^-2 are disordered over two set of sites with occupancy ratio of 0.541 (13):0.459 (13). The molecules are stabilized due to intra as well as inter-molecular H-bondings and C–H···π interactions (Table 1, Fig. 2). The π–π interaction between the centroids CgA and CgB of benzene rings A and B respectively, also play a role in the stabilization of molecules. The centroid to centroid distance is 3.842 (2) Å.

Related literature top

For background to the properties and uses of aminobenzoic acids, see: Griss et al. (1984); Pedanova et al. (1984); Refaat (2010); Rogers & Clark (1973).

Experimental top

Ethanolic solution of anthranilic acid (0.02 M) was refluxed in the presence of conc. H₂SO₄ (0.01 M) for 30 min. The contents were kept at room temperature for 24 h. The crystalline material formed was washed with n-hexane, ethyl acetate and diethyl ether, respectively and dried. This material was dissolverd in ethanol and colorless prisms of (I) were obtainesd by slow evaporation at room temperature.

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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level. The dotted lines show the hydogen bonds.

Bis(2-carboxyanilinium) sulfate monohydrate top

Crystal data top

2C₇H₈NO₂⁺·SO₄²⁻·H₂O	F(000) = 816
M_r = 390.36	D_x = 1.511 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3752 reflections
a = 11.260 (5) Å	θ = 2.0–27.1°
b = 10.542 (4) Å	µ = 0.24 mm⁻¹
c = 15.358 (5) Å	T = 296 K
β = 109.737 (5)°	Prisms, colorless
V = 1715.9 (12) Å³	0.28 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3748 independent reflections
Radiation source: fine-focus sealed tube	2528 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 7.50 pixels mm^-1	θ_max = 27.1°, θ_min = 2.0°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→13
T_min = 0.934, T_max = 0.955	l = −19→18
12530 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0551P)² + 0.3168P] where P = (F_o² + 2F_c²)/3
3748 reflections	(Δ/σ)_max < 0.001
282 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

2C₇H₈NO₂⁺·SO₄²⁻·H₂O	V = 1715.9 (12) Å³
M_r = 390.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.260 (5) Å	µ = 0.24 mm⁻¹
b = 10.542 (4) Å	T = 296 K
c = 15.358 (5) Å	0.28 × 0.25 × 0.20 mm
β = 109.737 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3748 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2528 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.955	R_int = 0.036
12530 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.22 e Å⁻³
3748 reflections	Δρ_min = −0.40 e Å⁻³
282 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	Occ. (<1)
O1	0.45161 (14)	0.45846 (15)	0.61664 (12)	0.0529 (6)
O2	0.24999 (14)	0.41658 (17)	0.58921 (13)	0.0613 (7)
N1	0.15921 (15)	0.19068 (17)	0.51077 (12)	0.0408 (6)
C1	0.36494 (17)	0.28683 (19)	0.51932 (13)	0.0326 (6)
C2	0.27346 (18)	0.19261 (19)	0.48532 (14)	0.0346 (6)
C3	0.2899 (2)	0.0970 (2)	0.43001 (16)	0.0459 (8)
C4	0.3988 (2)	0.0928 (2)	0.40722 (16)	0.0518 (8)
C5	0.4909 (2)	0.1840 (2)	0.44025 (15)	0.0478 (8)
C6	0.47351 (18)	0.2800 (2)	0.49500 (14)	0.0404 (7)
C7	0.34884 (18)	0.3926 (2)	0.57799 (14)	0.0357 (6)
O3	0.20126 (14)	0.69772 (16)	0.43653 (12)	0.0569 (6)
O4	0.01902 (14)	0.62640 (15)	0.44221 (12)	0.0557 (6)
N2	−0.09794 (14)	0.43896 (16)	0.32614 (12)	0.0364 (6)
C8	0.12219 (17)	0.51165 (19)	0.35454 (13)	0.0307 (6)
C9	0.02378 (18)	0.42708 (18)	0.31295 (13)	0.0308 (6)
C10	0.0387 (2)	0.3301 (2)	0.25830 (15)	0.0412 (7)
C11	0.1524 (2)	0.3134 (2)	0.24375 (16)	0.0488 (8)
C12	0.2513 (2)	0.3945 (2)	0.28460 (15)	0.0442 (7)
C13	0.23563 (18)	0.4927 (2)	0.33872 (14)	0.0376 (6)
C14	0.10804 (19)	0.6174 (2)	0.41481 (14)	0.0367 (7)
S1	0.82551 (5)	0.10652 (5)	0.37522 (4)	0.0404 (2)
O5A	0.7633 (7)	0.2145 (4)	0.3274 (4)	0.0608 (16)	0.541 (13)
O6A	0.9595 (4)	0.1055 (9)	0.3666 (3)	0.0576 (19)	0.541 (13)
O7A	0.8109 (9)	0.1137 (12)	0.4669 (9)	0.053 (2)	0.541 (13)
O8A	0.7732 (9)	−0.0123 (10)	0.3402 (8)	0.051 (2)	0.541 (13)
O5B	0.6994 (8)	0.1600 (10)	0.3072 (4)	0.078 (3)	0.459 (13)
O6B	0.9227 (7)	0.1737 (8)	0.3650 (3)	0.0500 (19)	0.459 (13)
O7B	0.8590 (9)	0.1102 (15)	0.4772 (10)	0.049 (2)	0.459 (13)
O8B	0.8163 (12)	−0.0309 (13)	0.3482 (10)	0.057 (3)	0.459 (13)
O9	0.55554 (17)	0.37630 (18)	0.26338 (13)	0.0535 (7)
H1	0.43834	0.51227	0.65081	0.0793*
H1A	0.09356	0.16783	0.46196	0.0612*
H1B	0.14569	0.26764	0.52934	0.0612*
H1C	0.16899	0.13539	0.55646	0.0612*
H3	0.22814	0.03516	0.40785	0.0551*
H4	0.40991	0.02812	0.36949	0.0622*
H5	0.56438	0.18049	0.42545	0.0573*
H6	0.53543	0.34189	0.51640	0.0484*
H2A	−0.15481	0.46829	0.27447	0.0546*
H2B	−0.09109	0.49252	0.37237	0.0546*
H2C	−0.12228	0.36332	0.33962	0.0546*
H3A	0.18855	0.75376	0.46936	0.0854*
H10	−0.02800	0.27507	0.23078	0.0495*
H11	0.16195	0.24753	0.20641	0.0586*
H12	0.32830	0.38297	0.27570	0.0531*
H13	0.30250	0.54790	0.36542	0.0451*
H9A	0.576 (3)	0.407 (3)	0.2229 (19)	0.0642*
H9B	0.607 (2)	0.313 (3)	0.2786 (18)	0.0642*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0400 (8)	0.0520 (11)	0.0720 (12)	−0.0148 (8)	0.0259 (8)	−0.0236 (9)
O2	0.0370 (9)	0.0661 (12)	0.0872 (13)	−0.0092 (8)	0.0294 (9)	−0.0292 (10)
N1	0.0334 (9)	0.0396 (11)	0.0503 (11)	−0.0066 (8)	0.0153 (8)	0.0028 (9)
C1	0.0296 (10)	0.0350 (12)	0.0325 (10)	−0.0007 (9)	0.0097 (8)	0.0052 (9)
C2	0.0318 (10)	0.0353 (12)	0.0369 (11)	0.0001 (9)	0.0117 (9)	0.0064 (10)
C3	0.0463 (12)	0.0388 (13)	0.0513 (14)	−0.0073 (11)	0.0147 (11)	−0.0023 (11)
C4	0.0571 (15)	0.0498 (15)	0.0506 (14)	0.0039 (12)	0.0209 (12)	−0.0097 (12)
C5	0.0390 (12)	0.0606 (16)	0.0478 (13)	0.0031 (12)	0.0200 (10)	−0.0015 (12)
C6	0.0316 (10)	0.0486 (14)	0.0401 (11)	−0.0039 (10)	0.0111 (9)	−0.0012 (11)
C7	0.0306 (10)	0.0365 (12)	0.0403 (11)	−0.0015 (9)	0.0125 (9)	0.0048 (10)
O3	0.0507 (9)	0.0519 (10)	0.0768 (13)	−0.0231 (8)	0.0328 (9)	−0.0311 (9)
O4	0.0425 (9)	0.0538 (10)	0.0792 (12)	−0.0122 (8)	0.0314 (9)	−0.0287 (9)
N2	0.0299 (9)	0.0365 (10)	0.0410 (10)	−0.0058 (8)	0.0095 (8)	−0.0005 (8)
C8	0.0290 (9)	0.0297 (11)	0.0302 (10)	−0.0005 (9)	0.0059 (8)	0.0015 (9)
C9	0.0304 (10)	0.0279 (11)	0.0315 (10)	0.0023 (9)	0.0070 (8)	0.0038 (9)
C10	0.0428 (12)	0.0328 (12)	0.0439 (12)	−0.0038 (10)	0.0091 (10)	−0.0067 (10)
C11	0.0585 (15)	0.0395 (13)	0.0495 (14)	0.0089 (12)	0.0196 (12)	−0.0070 (11)
C12	0.0386 (12)	0.0509 (14)	0.0453 (12)	0.0107 (11)	0.0169 (10)	0.0033 (12)
C13	0.0302 (10)	0.0409 (12)	0.0389 (11)	−0.0025 (9)	0.0082 (9)	0.0007 (10)
C14	0.0322 (10)	0.0341 (12)	0.0425 (12)	−0.0052 (9)	0.0111 (9)	−0.0047 (10)
S1	0.0493 (3)	0.0288 (3)	0.0455 (3)	−0.0044 (3)	0.0192 (3)	−0.0041 (3)
O5A	0.045 (3)	0.033 (2)	0.096 (3)	0.004 (2)	0.013 (2)	0.020 (2)
O6A	0.0306 (19)	0.080 (5)	0.061 (2)	−0.002 (2)	0.0141 (16)	0.007 (2)
O7A	0.075 (5)	0.039 (3)	0.058 (4)	−0.011 (5)	0.041 (5)	−0.014 (3)
O8A	0.065 (4)	0.026 (4)	0.048 (2)	−0.013 (3)	−0.001 (3)	−0.006 (2)
O5B	0.046 (4)	0.084 (5)	0.093 (4)	0.018 (4)	0.009 (3)	0.019 (3)
O6B	0.045 (3)	0.046 (4)	0.064 (3)	−0.015 (3)	0.025 (2)	0.005 (2)
O7B	0.061 (5)	0.043 (3)	0.047 (3)	−0.006 (5)	0.025 (5)	−0.009 (2)
O8B	0.099 (8)	0.028 (3)	0.057 (6)	−0.003 (5)	0.045 (6)	−0.004 (3)
O9	0.0570 (11)	0.0506 (11)	0.0635 (12)	−0.0020 (8)	0.0343 (9)	−0.0038 (9)

Geometric parameters (Å, º) top

S1—O7A	1.474 (13)	N2—H2B	0.8900
S1—O8A	1.411 (11)	C1—C2	1.399 (3)
S1—O5B	1.557 (8)	C1—C7	1.483 (3)
S1—O6B	1.356 (8)	C1—C6	1.396 (3)
S1—O7B	1.483 (14)	C2—C3	1.370 (3)
S1—O5A	1.407 (5)	C3—C4	1.385 (3)
S1—O6A	1.559 (5)	C4—C5	1.379 (3)
S1—O8B	1.501 (14)	C5—C6	1.371 (3)
O1—C7	1.308 (3)	C3—H3	0.9300
O2—C7	1.209 (3)	C4—H4	0.9300
O1—H1	0.8200	C5—H5	0.9300
O3—C14	1.301 (3)	C6—H6	0.9300
O4—C14	1.215 (3)	C8—C13	1.393 (3)
O3—H3A	0.8200	C8—C14	1.492 (3)
O9—H9A	0.80 (3)	C8—C9	1.397 (3)
O9—H9B	0.86 (3)	C9—C10	1.369 (3)
N1—C2	1.466 (3)	C10—C11	1.383 (3)
N1—H1A	0.8900	C11—C12	1.376 (3)
N1—H1C	0.8900	C12—C13	1.376 (3)
N1—H1B	0.8900	C10—H10	0.9300
N2—C9	1.457 (3)	C11—H11	0.9300
N2—H2A	0.8900	C12—H12	0.9300
N2—H2C	0.8900	C13—H13	0.9300

O5B—S1—O7B	123.3 (6)	C4—C5—C6	119.7 (2)
O5B—S1—O8B	101.6 (7)	C1—C6—C5	121.4 (2)
O6B—S1—O7B	100.4 (5)	O1—C7—C1	113.84 (18)
O6B—S1—O8B	117.1 (6)	O1—C7—O2	122.7 (2)
O7B—S1—O8B	106.7 (8)	O2—C7—C1	123.5 (2)
O5A—S1—O8A	116.7 (5)	C4—C3—H3	120.00
O6A—S1—O7A	120.3 (5)	C2—C3—H3	120.00
O6A—S1—O8A	104.7 (6)	C3—C4—H4	120.00
O7A—S1—O8A	104.1 (7)	C5—C4—H4	120.00
O5B—S1—O6B	108.8 (5)	C4—C5—H5	120.00
O5A—S1—O6A	106.7 (4)	C6—C5—H5	120.00
O5A—S1—O7A	105.1 (6)	C5—C6—H6	119.00
C7—O1—H1	109.00	C1—C6—H6	119.00
C14—O3—H3A	109.00	C9—C8—C13	117.46 (18)
H9A—O9—H9B	100 (3)	C9—C8—C14	121.75 (18)
C2—N1—H1B	109.00	C13—C8—C14	120.79 (18)
H1B—N1—H1C	109.00	N2—C9—C10	117.75 (18)
H1A—N1—H1B	109.00	N2—C9—C8	121.31 (17)
C2—N1—H1A	109.00	C8—C9—C10	121.0 (2)
H1A—N1—H1C	109.00	C9—C10—C11	120.4 (2)
C2—N1—H1C	109.00	C10—C11—C12	119.9 (2)
C9—N2—H2C	109.00	C11—C12—C13	119.6 (2)
C9—N2—H2B	109.00	C8—C13—C12	121.7 (2)
C9—N2—H2A	109.00	O4—C14—C8	123.2 (2)
H2A—N2—H2C	109.00	O3—C14—C8	113.54 (19)
H2A—N2—H2B	109.00	O3—C14—O4	123.3 (2)
H2B—N2—H2C	109.00	C11—C10—H10	120.00
C2—C1—C7	122.35 (18)	C9—C10—H10	120.00
C2—C1—C6	117.69 (18)	C10—C11—H11	120.00
C6—C1—C7	119.96 (18)	C12—C11—H11	120.00
N1—C2—C3	118.01 (19)	C13—C12—H12	120.00
N1—C2—C1	120.82 (18)	C11—C12—H12	120.00
C1—C2—C3	121.1 (2)	C12—C13—H13	119.00
C2—C3—C4	119.8 (2)	C8—C13—H13	119.00
C3—C4—C5	120.3 (2)

C6—C1—C2—N1	177.63 (18)	C13—C8—C9—N2	179.56 (18)
C6—C1—C2—C3	0.0 (3)	C13—C8—C9—C10	−0.5 (3)
C7—C1—C2—N1	−3.4 (3)	C14—C8—C9—N2	0.4 (3)
C7—C1—C2—C3	179.0 (2)	C14—C8—C9—C10	−179.60 (19)
C2—C1—C6—C5	−0.5 (3)	C9—C8—C13—C12	−0.2 (3)
C7—C1—C6—C5	−179.48 (19)	C14—C8—C13—C12	178.92 (19)
C2—C1—C7—O1	168.59 (19)	C9—C8—C14—O3	−170.35 (18)
C2—C1—C7—O2	−11.6 (3)	C9—C8—C14—O4	10.8 (3)
C6—C1—C7—O1	−12.4 (3)	C13—C8—C14—O3	10.5 (3)
C6—C1—C7—O2	167.4 (2)	C13—C8—C14—O4	−168.3 (2)
N1—C2—C3—C4	−177.61 (19)	N2—C9—C10—C11	−179.52 (19)
C1—C2—C3—C4	0.1 (3)	C8—C9—C10—C11	0.5 (3)
C2—C3—C4—C5	0.3 (3)	C9—C10—C11—C12	0.2 (3)
C3—C4—C5—C6	−0.8 (3)	C10—C11—C12—C13	−0.8 (3)
C4—C5—C6—C1	0.9 (3)	C11—C12—C13—C8	0.9 (3)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O6Aⁱ	0.89	1.83	2.721 (6)	174
N1—H1B···O2	0.89	1.99	2.708 (3)	137
N1—H1B···O4ⁱⁱ	0.89	2.33	3.041 (3)	137
N1—H1C···O8Aⁱⁱⁱ	0.89	1.98	2.860 (11)	168
N2—H2A···O8A^iv	0.89	1.83	2.698 (12)	166
N2—H2B···O4	0.89	1.94	2.689 (3)	140
N2—H2B···O2ⁱⁱ	0.89	2.28	2.906 (3)	128
N2—H2C···O5Aⁱ	0.89	2.00	2.839 (6)	157
O1—H1···O9^v	0.82	1.75	2.557 (3)	168
O3—H3A···O7A^v	0.82	1.70	2.512 (13)	167
O9—H9A···O6A^vi	0.80 (3)	2.46 (3)	3.102 (8)	138 (3)
O9—H9A···O8A^vi	0.80 (3)	2.38 (4)	3.115 (11)	153 (3)
O9—H9B···O5A	0.86 (3)	1.96 (3)	2.792 (7)	161 (3)
C4—H4···Cg2^vii	0.93	2.75	3.600 (3)	153

Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) −x+1/2, y+1/2, −z+1/2; (v) −x+1, −y+1, −z+1; (vi) −x+3/2, y+1/2, −z+1/2; (vii) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	2C₇H₈NO₂⁺·SO₄²⁻·H₂O
M_r	390.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	11.260 (5), 10.542 (4), 15.358 (5)
β (°)	109.737 (5)
V (Å³)	1715.9 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.28 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.934, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	12530, 3748, 2528
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.118, 1.02
No. of reflections	3748
No. of parameters	282
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.40

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O6Aⁱ	0.89	1.83	2.721 (6)	174
N1—H1B···O2	0.89	1.99	2.708 (3)	137
N1—H1B···O4ⁱⁱ	0.89	2.33	3.041 (3)	137
N1—H1C···O8Aⁱⁱⁱ	0.89	1.98	2.860 (11)	168
N2—H2A···O8A^iv	0.89	1.83	2.698 (12)	166
N2—H2B···O4	0.89	1.94	2.689 (3)	140
N2—H2B···O2ⁱⁱ	0.89	2.28	2.906 (3)	128
N2—H2C···O5Aⁱ	0.89	2.00	2.839 (6)	157
O1—H1···O9^v	0.82	1.75	2.557 (3)	168
O3—H3A···O7A^v	0.82	1.70	2.512 (13)	167
O9—H9A···O6A^vi	0.80 (3)	2.46 (3)	3.102 (8)	138 (3)
O9—H9A···O8A^vi	0.80 (3)	2.38 (4)	3.115 (11)	153 (3)
O9—H9B···O5A	0.86 (3)	1.96 (3)	2.792 (7)	161 (3)
C4—H4···Cg2^vii	0.93	2.75	3.600 (3)	153

Acknowledgements

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Bana International, Karachi, Pakistan.

References

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Volume 66| Part 4| April 2010| Page o819

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