Literature DB >> 24454147

Uronium 3-carb-oxy-4-hy-droxy-benzene-sulfonate.

A Silambarasan¹, M Krishna Kumar¹, G Chakkaravarthi², R Mohan Kumar¹, P R Umarani³.

Abstract

In the title compound, CH5N2O(+)·C7H5O6S(-), the dihedral angle between the benzene ring and the mean plane of the uronium cation is 76.02 (8)°. The carboxyl group in the anion is twisted by 1.47 (9)° from the benzene ring. In the crystal, the cation is linked to the anion by weak O-H⋯O and N-H⋯O hydrogen bonds and π-π inter-actions [centroid-centroid distance = 3.8859 (8) Å], forming a three-dimensional network.

Entities: Chemical Disease Gene

Year: 2013 PMID： 24454147 PMCID： PMC3884371 DOI： 10.1107/S1600536813029474

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

Related literature

For the biological activity of urea derivatives, see: Sliskovic et al. (1999 ▶); Furlong et al. (2000 ▶); Houghton et al. (1995 ▶). For related structures, see: Krishnakumar et al. (2012 ▶); Sudhahar et al. (2013 ▶); Worsham & Busing (1969 ▶); Nelyubina et al. (2007 ▶).

Experimental

Crystal data

CH5N2O+·C7H5O6S− M = 278.24 Triclinic, a = 7.2248 (4) Å b = 8.7718 (5) Å c = 10.1549 (5) Å α = 85.504 (3)° β = 71.087 (2)° γ = 68.659 (2)° V = 566.50 (5) Å3 Z = 2 Mo Kα radiation μ = 0.32 mm−1 T = 295 K 0.30 × 0.24 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.911, T max = 0.939 14246 measured reflections 4079 independent reflections 3432 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.110 S = 1.05 4079 reflections 185 parameters 7 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.41 e Å−3 Δρmin = −0.40 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813029474/bh2485sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813029474/bh2485Isup2.hkl 968736 Additional supplementary materials: crystallographic information; 3D view; checkCIF report

CH₅N₂O⁺·C₇H₅O₆S⁻	Z = 2
M_r = 278.24	F(000) = 288
Triclinic, P1	D_x = 1.631 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2248 (4) Å	Cell parameters from 7318 reflections
b = 8.7718 (5) Å	θ = 2.1–32.8°
c = 10.1549 (5) Å	µ = 0.32 mm⁻¹
α = 85.504 (3)°	T = 295 K
β = 71.087 (2)°	Block, colourless
γ = 68.659 (2)°	0.30 × 0.24 × 0.20 mm
V = 566.50 (5) Å³

Bruker APEXII CCD diffractometer	4079 independent reflections
Radiation source: fine-focus sealed tube	3432 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω and φ scan	θ_max = 33.6°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
T_min = 0.911, T_max = 0.939	k = −13→13
14246 measured reflections	l = −14→15

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0577P)² + 0.1089P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4079 reflections	Δρ_max = 0.41 e Å⁻³
185 parameters	Δρ_min = −0.40 e Å⁻³
7 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.105 (7)
Primary atom site location: structure-invariant direct methods

	x	y	z	U_iso*/U_eq
C1	0.22603 (17)	0.52320 (13)	0.56728 (12)	0.0301 (2)
C2	0.28443 (18)	0.45643 (14)	0.43261 (12)	0.0324 (2)
C3	0.3015 (2)	0.29542 (15)	0.41388 (13)	0.0376 (3)
H3	0.3363	0.2524	0.3246	0.045*
C4	0.26724 (19)	0.20039 (14)	0.52622 (13)	0.0347 (2)
H4	0.2801	0.0928	0.5132	0.042*
C5	0.21286 (17)	0.26557 (12)	0.66054 (12)	0.0288 (2)
C6	0.19033 (17)	0.42571 (13)	0.68131 (12)	0.0301 (2)
H6	0.1514	0.4687	0.7712	0.036*
C7	0.20231 (19)	0.69528 (14)	0.58615 (14)	0.0343 (2)
C8	0.5164 (2)	0.26399 (16)	1.00316 (13)	0.0378 (3)
N1	0.6134 (2)	0.16284 (17)	0.89415 (14)	0.0474 (3)
N2	0.6150 (2)	0.32507 (16)	1.05987 (13)	0.0431 (3)
O1	0.1437 (2)	0.74360 (11)	0.71788 (11)	0.0490 (3)
O2	0.23382 (18)	0.78366 (11)	0.48953 (11)	0.0473 (2)
O3	0.32586 (18)	0.54310 (12)	0.31773 (10)	0.0459 (2)
O4	0.39451 (15)	0.02256 (11)	0.79035 (11)	0.0417 (2)
O5	0.05090 (15)	0.05458 (11)	0.78561 (11)	0.0417 (2)
O6	0.08949 (15)	0.24191 (11)	0.92865 (9)	0.0380 (2)
O7	0.31385 (16)	0.31219 (15)	1.06119 (12)	0.0513 (3)
S1	0.18626 (4)	0.13680 (3)	0.80111 (3)	0.03090 (10)
H1A	0.551 (2)	0.1153 (18)	0.8654 (16)	0.037*
H1B	0.7463 (14)	0.1303 (19)	0.8589 (15)	0.037*
H2A	0.543 (2)	0.3875 (17)	1.1326 (12)	0.037*
H2B	0.7490 (14)	0.2929 (19)	1.0274 (16)	0.037*
H1	0.129 (3)	0.8404 (12)	0.7270 (18)	0.046*
H3A	0.303 (3)	0.6342 (14)	0.3493 (18)	0.046*
H7	0.253 (3)	0.278 (2)	1.0221 (17)	0.046*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0310 (5)	0.0228 (4)	0.0369 (6)	−0.0100 (4)	−0.0100 (4)	−0.0027 (4)
C2	0.0333 (5)	0.0287 (5)	0.0338 (6)	−0.0102 (4)	−0.0095 (4)	−0.0006 (4)
C3	0.0466 (6)	0.0317 (5)	0.0328 (6)	−0.0125 (5)	−0.0105 (5)	−0.0068 (4)
C4	0.0412 (6)	0.0245 (5)	0.0382 (6)	−0.0114 (4)	−0.0110 (5)	−0.0070 (4)
C5	0.0300 (4)	0.0222 (4)	0.0341 (5)	−0.0099 (4)	−0.0083 (4)	−0.0037 (4)
C6	0.0342 (5)	0.0237 (4)	0.0327 (5)	−0.0115 (4)	−0.0082 (4)	−0.0053 (4)
C7	0.0361 (5)	0.0244 (5)	0.0434 (6)	−0.0117 (4)	−0.0123 (5)	−0.0015 (4)
C8	0.0418 (6)	0.0372 (6)	0.0358 (6)	−0.0163 (5)	−0.0127 (5)	0.0067 (5)
N1	0.0385 (6)	0.0541 (7)	0.0480 (7)	−0.0165 (5)	−0.0089 (5)	−0.0101 (5)
N2	0.0458 (6)	0.0439 (6)	0.0433 (6)	−0.0191 (5)	−0.0152 (5)	0.0014 (5)
O1	0.0766 (7)	0.0265 (4)	0.0465 (5)	−0.0241 (5)	−0.0149 (5)	−0.0053 (4)
O2	0.0630 (6)	0.0306 (4)	0.0512 (6)	−0.0213 (4)	−0.0176 (5)	0.0064 (4)
O3	0.0634 (6)	0.0374 (5)	0.0356 (5)	−0.0196 (5)	−0.0130 (4)	0.0036 (4)
O4	0.0428 (5)	0.0284 (4)	0.0487 (5)	−0.0056 (4)	−0.0155 (4)	−0.0018 (4)
O5	0.0445 (5)	0.0310 (4)	0.0515 (5)	−0.0216 (4)	−0.0064 (4)	−0.0068 (4)
O6	0.0445 (5)	0.0331 (4)	0.0337 (4)	−0.0155 (4)	−0.0052 (3)	−0.0066 (3)
O7	0.0402 (5)	0.0632 (7)	0.0490 (6)	−0.0176 (5)	−0.0095 (4)	−0.0137 (5)
S1	0.03538 (15)	0.02207 (13)	0.03448 (16)	−0.01185 (10)	−0.00736 (11)	−0.00307 (9)

C1—C6	1.3966 (16)	C8—O7	1.3029 (16)
C1—C2	1.4010 (16)	C8—N1	1.3047 (17)
C1—C7	1.4766 (15)	C8—N2	1.3104 (18)
C2—O3	1.3523 (15)	N1—H1A	0.841 (9)
C2—C3	1.3951 (17)	N1—H1B	0.852 (9)
C3—C4	1.3695 (18)	N2—H2A	0.850 (9)
C3—H3	0.9300	N2—H2B	0.858 (9)
C4—C5	1.3976 (15)	O1—H1	0.826 (9)
C4—H4	0.9300	O3—H3A	0.824 (9)
C5—C6	1.3791 (14)	O4—S1	1.4468 (10)
C5—S1	1.7544 (12)	O5—S1	1.4602 (9)
C6—H6	0.9300	O6—S1	1.4654 (9)
C7—O2	1.2165 (16)	O7—H7	0.821 (9)
C7—O1	1.3189 (16)

C6—C1—C2	119.27 (10)	O1—C7—C1	113.41 (11)
C6—C1—C7	121.23 (10)	O7—C8—N1	121.64 (12)
C2—C1—C7	119.50 (11)	O7—C8—N2	115.88 (12)
O3—C2—C3	117.87 (11)	N1—C8—N2	122.48 (13)
O3—C2—C1	122.19 (10)	C8—N1—H1A	121.2 (11)
C3—C2—C1	119.95 (11)	C8—N1—H1B	120.5 (11)
C4—C3—C2	120.39 (11)	H1A—N1—H1B	117.5 (15)
C4—C3—H3	119.8	C8—N2—H2A	117.9 (11)
C2—C3—H3	119.8	C8—N2—H2B	118.8 (11)
C3—C4—C5	119.82 (10)	H2A—N2—H2B	123.0 (15)
C3—C4—H4	120.1	C7—O1—H1	112.4 (12)
C5—C4—H4	120.1	C2—O3—H3A	103.8 (13)
C6—C5—C4	120.59 (11)	C8—O7—H7	115.2 (13)
C6—C5—S1	120.71 (9)	O4—S1—O5	112.06 (6)
C4—C5—S1	118.63 (8)	O4—S1—O6	112.49 (6)
C5—C6—C1	119.95 (10)	O5—S1—O6	111.64 (5)
C5—C6—H6	120.0	O4—S1—C5	106.92 (6)
C1—C6—H6	120.0	O5—S1—C5	106.35 (6)
O2—C7—O1	123.37 (11)	O6—S1—C5	106.94 (5)
O2—C7—C1	123.22 (11)

C6—C1—C2—O3	−178.47 (11)	C7—C1—C6—C5	179.73 (10)
C7—C1—C2—O3	1.84 (18)	C6—C1—C7—O2	179.30 (12)
C6—C1—C2—C3	1.51 (17)	C2—C1—C7—O2	−1.02 (18)
C7—C1—C2—C3	−178.18 (11)	C6—C1—C7—O1	−0.71 (16)
O3—C2—C3—C4	178.12 (12)	C2—C1—C7—O1	178.98 (11)
C1—C2—C3—C4	−1.86 (19)	C6—C5—S1—O4	−106.66 (10)
C2—C3—C4—C5	0.64 (19)	C4—C5—S1—O4	70.32 (10)
C3—C4—C5—C6	0.94 (18)	C6—C5—S1—O5	133.45 (9)
C3—C4—C5—S1	−176.05 (10)	C4—C5—S1—O5	−49.56 (10)
C4—C5—C6—C1	−1.28 (17)	C6—C5—S1—O6	14.04 (11)
S1—C5—C6—C1	175.65 (8)	C4—C5—S1—O6	−168.98 (9)
C2—C1—C6—C5	0.05 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.82 (1)	1.83 (1)	2.5966 (14)	154 (18)
O7—H7···O6	0.82 (1)	1.85 (1)	2.6629 (14)	169 (18)
N1—H1A···O4	0.84 (1)	1.96 (1)	2.7979 (16)	175 (16)
O1—H1···O5ⁱ	0.83 (1)	1.84 (1)	2.6511 (12)	167 (18)
N1—H1B···O5ⁱⁱ	0.85 (1)	1.95 (1)	2.7976 (16)	178 (15)
N2—H2B···O6ⁱⁱ	0.86 (1)	2.22 (1)	3.0712 (16)	172 (15)
N2—H2A···O3ⁱⁱⁱ	0.85 (1)	2.19 (1)	3.0347 (16)	173 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2	0.82 (1)	1.83 (1)	2.5966 (14)	154 (18)
O7—H7⋯O6	0.82 (1)	1.85 (1)	2.6629 (14)	169 (18)
N1—H1A⋯O4	0.84 (1)	1.96 (1)	2.7979 (16)	175 (16)
O1—H1⋯O5ⁱ	0.83 (1)	1.84 (1)	2.6511 (12)	167 (18)
N1—H1B⋯O5ⁱⁱ	0.85 (1)	1.95 (1)	2.7976 (16)	178 (15)
N2—H2B⋯O6ⁱⁱ	0.86 (1)	2.22 (1)	3.0712 (16)	172 (15)
N2—H2A⋯O3ⁱⁱⁱ	0.85 (1)	2.19 (1)	3.0347 (16)	173 (15)

Symmetry codes: (i) ; (ii) ; (iii) .

6 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. Routine determination of sulfonylurea, imidazolinone, and sulfonamide herbicides at nanogram-per-liter concentrations by solid-phase extraction and liquid chromatography/mass spectrometry.

Authors: E T Furlong; M R Burkhardt; P M Gates; S L Werner; W A Battaglin
Journal: Sci Total Environ Date: 2000-04-05 Impact factor: 7.963

3. Characterization of the intracellular distribution and binding in human adenocarcinoma cells of N-(4-azidophenylsulfonyl)-N'-(4-chlorophenyl)urea (LY219703), a photoaffinity analogue of the antitumor diarylsulfonylurea sulofenur.

Authors: P J Houghton; J Sosinski; J H Thakar; G B Boder; G B Grindey
Journal: Biochem Pharmacol Date: 1995-03-01 Impact factor: 5.858