Literature DB >> 21580650

Bis(2-carboxy-anilinium) sulfate monohydrate.

Taslim Akhtar, Khawar Masih, M Nawaz Tahir, Muhammad Ilyas Tariq, Shahid Iqbal.

Abstract

In the title hydrated mol-ecular salt, 2C(7)H(8)NO(2) (+)·SO(4) (2-)·H(2)O, each cation in the asymmetric unit is stabilized by an intra-molecular 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 inter-action.

Entities: Chemical Disease Gene

Year: 2010 PMID： 21580650 PMCID： PMC2983959 DOI： 10.1107/S1600536810008913

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

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 +·SO4 2−·H2O M = 390.36 Monoclinic, 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[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.118 S = 1.02 3748 reflections 282 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.22 e Å−3 Δρmin = −0.40 e Å−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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810008913/hb5357sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008913/hb5357Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

Bruker Kappa APEXII CCD diffractometer	3748 independent reflections
Radiation source: fine-focus sealed tube	2528 reflections with I > 2σ(I)
graphite	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 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

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.

	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*

	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)

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)

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

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) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20

2 in total

1 in total

1. 2-(Morpholinium-4-yl)ethyl-ammonium sulfate methanol monosolvate.

Authors: Ye Bi
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-03-27

1 in total