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

In the anion of the title salt, C2H6NO2 (+)·C7H5O6S(-), the dihedral angle between the carb-oxy-lic acid group and the benzene ring is 5.02 (12)°. In the crystal, the anions are linked into inversion dimers through pairs of O-H⋯O hydrogen bonds between the carb-oxy-lic acid groups and sulfonate O atoms. A pair of C-H⋯O inter-actions is also observed within each dimer. The anion dimers and the cations are linked into a three-dimensional network by N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For background to non-linear optical materials, see: Yang et al. (2005 ▶); Kumar et al. (2009 ▶). For related structures, see: Krishnakumar et al. (2012 ▶); Sudhahar et al. (2013 ▶).

Experimental

Crystal data

C2H6NO2 +·C7H5O6S−

M = 293.25

Monoclinic,

a = 5.3651 (3) Å

b = 24.7207 (15) Å

c = 8.6840 (5) Å

β = 90.170 (2)°

V = 1151.75 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 295 K

0.36 × 0.32 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.893, T max = 0.910

21406 measured reflections

3694 independent reflections

3282 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.117

S = 1.20

3694 reflections

197 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.53 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/S1600536814004590/is5343sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004590/is5343Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814004590/is5343Isup3.cml

CCDC reference: 989106

Additional supporting information: crystallographic information; 3D view; checkCIF report

C2H6NO2+·C7H5O6S−	F(000) = 608
Mr = 293.25	Dx = 1.691 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9634 reflections
a = 5.3651 (3) Å	θ = 2.5–32.0°
b = 24.7207 (15) Å	µ = 0.32 mm−1
c = 8.6840 (5) Å	T = 295 K
β = 90.170 (2)°	Block, colourless
V = 1151.75 (12) Å3	0.36 × 0.32 × 0.30 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3694 independent reflections
Radiation source: fine-focus sealed tube	3282 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω and φ scan	θmax = 32.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.893, Tmax = 0.910	k = −36→36
21406 measured reflections	l = −12→12

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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.0325P)2 + 1.2564P] where P = (Fo2 + 2Fc2)/3
S = 1.20	(Δ/σ)max < 0.001
3694 reflections	Δρmax = 0.49 e Å−3
197 parameters	Δρmin = −0.53 e Å−3
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.071 (3)

	x	y	z	Uiso*/Ueq
C1	0.5636 (3)	0.41186 (7)	0.7824 (2)	0.0177 (3)
C2	0.6669 (3)	0.46042 (7)	0.8273 (2)	0.0194 (3)
H2	0.8074	0.4607	0.8903	0.023*
C3	0.5608 (3)	0.50936 (7)	0.7784 (2)	0.0198 (3)
C4	0.3495 (4)	0.50846 (8)	0.6831 (2)	0.0244 (4)
C5	0.2445 (4)	0.45897 (8)	0.6403 (3)	0.0283 (4)
H5	0.1027	0.4583	0.5785	0.034*
C6	0.3505 (4)	0.41112 (8)	0.6893 (2)	0.0244 (4)
H6	0.2801	0.3783	0.6603	0.029*
C7	0.6683 (4)	0.56133 (7)	0.8269 (2)	0.0248 (4)
C8	0.8846 (4)	0.69748 (7)	0.6240 (2)	0.0213 (3)
C9	0.8379 (4)	0.71637 (8)	0.7865 (2)	0.0221 (3)
H9A	0.9096	0.6908	0.8589	0.026*
H9B	0.9166	0.7512	0.8028	0.026*
N1	0.5669 (3)	0.72092 (7)	0.81273 (19)	0.0219 (3)
O1	0.2384 (3)	0.55374 (7)	0.6301 (2)	0.0398 (4)
O2	0.8214 (3)	0.32854 (7)	0.69766 (18)	0.0377 (4)
O3	0.5004 (3)	0.31390 (6)	0.88206 (18)	0.0305 (3)
O4	0.8755 (3)	0.36047 (6)	0.9590 (2)	0.0364 (4)
O5	0.8540 (3)	0.55664 (6)	0.9256 (2)	0.0364 (4)
O6	0.5921 (3)	0.60513 (6)	0.7813 (2)	0.0380 (4)
O7	1.1214 (3)	0.68486 (8)	0.60241 (19)	0.0386 (4)
O8	0.7240 (3)	0.69592 (6)	0.52779 (16)	0.0278 (3)
S1	0.70129 (8)	0.349884 (16)	0.83495 (5)	0.01747 (12)
H1A	0.489 (6)	0.6942 (10)	0.771 (4)	0.059 (10)*
H1B	0.515 (6)	0.7512 (8)	0.774 (4)	0.059 (10)*
H1C	0.528 (6)	0.7171 (14)	0.9088 (15)	0.059 (10)*
H5A	0.910 (6)	0.5865 (7)	0.949 (4)	0.051 (9)*
H7	1.134 (6)	0.6766 (12)	0.5112 (15)	0.048 (9)*
H1	0.320 (6)	0.5791 (10)	0.665 (4)	0.064 (11)*

	U11	U22	U33	U12	U13	U23
C1	0.0206 (8)	0.0139 (7)	0.0186 (8)	−0.0001 (6)	−0.0015 (6)	−0.0008 (6)
C2	0.0198 (8)	0.0163 (7)	0.0219 (8)	−0.0006 (6)	−0.0050 (6)	−0.0003 (6)
C3	0.0229 (8)	0.0147 (7)	0.0218 (8)	−0.0006 (6)	−0.0037 (6)	0.0001 (6)
C4	0.0261 (9)	0.0201 (8)	0.0270 (9)	0.0030 (7)	−0.0065 (7)	0.0031 (7)
C5	0.0249 (9)	0.0258 (9)	0.0342 (11)	0.0013 (7)	−0.0141 (8)	−0.0010 (8)
C6	0.0249 (9)	0.0196 (8)	0.0286 (9)	−0.0025 (6)	−0.0071 (7)	−0.0034 (7)
C7	0.0292 (10)	0.0161 (7)	0.0291 (9)	−0.0014 (6)	−0.0055 (8)	0.0003 (7)
C8	0.0271 (9)	0.0181 (7)	0.0186 (8)	−0.0005 (6)	0.0015 (7)	0.0008 (6)
C9	0.0255 (9)	0.0238 (8)	0.0169 (8)	−0.0034 (7)	−0.0012 (6)	−0.0017 (6)
N1	0.0278 (8)	0.0198 (7)	0.0181 (7)	−0.0003 (6)	0.0008 (6)	−0.0003 (6)
O1	0.0426 (9)	0.0232 (7)	0.0534 (11)	0.0065 (7)	−0.0235 (8)	0.0052 (7)
O2	0.0510 (10)	0.0343 (8)	0.0279 (8)	0.0189 (7)	0.0124 (7)	0.0003 (6)
O3	0.0374 (8)	0.0217 (6)	0.0324 (8)	−0.0097 (6)	0.0019 (6)	0.0069 (6)
O4	0.0463 (9)	0.0209 (7)	0.0419 (9)	0.0003 (6)	−0.0261 (8)	−0.0003 (6)
O5	0.0452 (9)	0.0190 (7)	0.0449 (9)	−0.0059 (6)	−0.0232 (8)	−0.0013 (6)
O6	0.0492 (10)	0.0150 (6)	0.0496 (10)	0.0014 (6)	−0.0166 (8)	0.0022 (6)
O7	0.0282 (8)	0.0602 (11)	0.0274 (8)	0.0057 (7)	0.0009 (6)	−0.0083 (7)
O8	0.0328 (8)	0.0322 (7)	0.0183 (6)	0.0033 (6)	−0.0035 (5)	−0.0020 (5)
S1	0.0230 (2)	0.01263 (18)	0.0168 (2)	−0.00042 (14)	−0.00211 (14)	−0.00052 (13)

C1—C2	1.378 (2)	C8—O7	1.322 (2)
C1—C6	1.399 (3)	C8—C9	1.508 (3)
C1—S1	1.7605 (17)	C9—N1	1.477 (3)
C2—C3	1.402 (2)	C9—H9A	0.9700
C2—H2	0.9300	C9—H9B	0.9700
C3—C4	1.402 (3)	N1—H1A	0.863 (10)
C3—C7	1.470 (2)	N1—H1B	0.866 (10)
C4—O1	1.348 (2)	N1—H1C	0.865 (10)
C4—C5	1.397 (3)	O1—H1	0.823 (10)
C5—C6	1.379 (3)	O2—S1	1.4559 (15)
C5—H5	0.9300	O3—S1	1.4570 (14)
C6—H6	0.9300	O4—S1	1.4478 (15)
C7—O6	1.223 (2)	O5—H5A	0.822 (10)
C7—O5	1.317 (2)	O7—H7	0.821 (10)
C8—O8	1.199 (2)
C2—C1—C6	120.16 (16)	O7—C8—C9	111.59 (17)
C2—C1—S1	121.11 (13)	N1—C9—C8	109.53 (15)
C6—C1—S1	118.69 (13)	N1—C9—H9A	109.8
C1—C2—C3	120.21 (16)	C8—C9—H9A	109.8
C1—C2—H2	119.9	N1—C9—H9B	109.8
C3—C2—H2	119.9	C8—C9—H9B	109.8
C4—C3—C2	119.48 (16)	H9A—C9—H9B	108.2
C4—C3—C7	119.94 (16)	C9—N1—H1A	111 (2)
C2—C3—C7	120.58 (16)	C9—N1—H1B	109 (2)
O1—C4—C5	117.33 (17)	H1A—N1—H1B	110 (3)
O1—C4—C3	122.96 (17)	C9—N1—H1C	112 (2)
C5—C4—C3	119.71 (17)	H1A—N1—H1C	102 (3)
C6—C5—C4	120.24 (18)	H1B—N1—H1C	113 (3)
C6—C5—H5	119.9	C4—O1—H1	106 (3)
C4—C5—H5	119.9	C7—O5—H5A	111 (2)
C5—C6—C1	120.18 (17)	C8—O7—H7	106 (2)
C5—C6—H6	119.9	O4—S1—O2	112.85 (11)
C1—C6—H6	119.9	O4—S1—O3	112.21 (10)
O6—C7—O5	122.70 (18)	O2—S1—O3	109.77 (10)
O6—C7—C3	123.42 (18)	O4—S1—C1	107.75 (8)
O5—C7—C3	113.88 (16)	O2—S1—C1	106.85 (9)
O8—C8—O7	125.65 (18)	O3—S1—C1	107.09 (9)
O8—C8—C9	122.73 (18)
C6—C1—C2—C3	−0.8 (3)	C4—C3—C7—O6	−4.4 (3)
S1—C1—C2—C3	177.08 (14)	C2—C3—C7—O6	175.9 (2)
C1—C2—C3—C4	−0.2 (3)	C4—C3—C7—O5	175.01 (19)
C1—C2—C3—C7	179.42 (18)	C2—C3—C7—O5	−4.7 (3)
C2—C3—C4—O1	−179.32 (19)	O8—C8—C9—N1	11.5 (2)
C7—C3—C4—O1	1.0 (3)	O7—C8—C9—N1	−170.32 (16)
C2—C3—C4—C5	1.2 (3)	C2—C1—S1—O4	16.02 (18)
C7—C3—C4—C5	−178.49 (19)	C6—C1—S1—O4	−166.12 (16)
O1—C4—C5—C6	179.4 (2)	C2—C1—S1—O2	−105.50 (17)
C3—C4—C5—C6	−1.1 (3)	C6—C1—S1—O2	72.36 (17)
C4—C5—C6—C1	0.1 (3)	C2—C1—S1—O3	136.93 (15)
C2—C1—C6—C5	0.8 (3)	C6—C1—S1—O3	−45.21 (17)
S1—C1—C6—C5	−177.06 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O6	0.82 (1)	1.89 (2)	2.631 (2)	150 (4)
N1—H1A···O6	0.86 (1)	2.27 (3)	2.878 (2)	127 (3)
N1—H1A···O7i	0.86 (1)	2.46 (3)	3.134 (2)	135 (3)
N1—H1B···O3ii	0.87 (1)	2.06 (2)	2.876 (2)	157 (3)
N1—H1C···O3iii	0.87 (1)	1.98 (2)	2.811 (2)	161 (3)
O5—H5A···O4iv	0.82 (1)	1.92 (2)	2.702 (2)	159 (3)
O7—H7···O2v	0.82 (1)	1.84 (1)	2.646 (2)	169 (3)
C2—H2···O5iv	0.93	2.45	3.370 (2)	168
C9—H9A···O4iv	0.97	2.33	3.292 (2)	172
C6—H6···O8vi	0.93	2.46	3.273 (2)	147
C9—H9B···O2vii	0.97	2.37	3.324 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O6	0.82 (1)	1.89 (2)	2.631 (2)	150 (4)
N1—H1A⋯O6	0.86 (1)	2.27 (3)	2.878 (2)	127 (3)
N1—H1A⋯O7i	0.86 (1)	2.46 (3)	3.134 (2)	135 (3)
N1—H1B⋯O3ii	0.87 (1)	2.06 (2)	2.876 (2)	157 (3)
N1—H1C⋯O3iii	0.87 (1)	1.98 (2)	2.811 (2)	161 (3)
O5—H5A⋯O4iv	0.82 (1)	1.92 (2)	2.702 (2)	159 (3)
O7—H7⋯O2v	0.82 (1)	1.84 (1)	2.646 (2)	169 (3)
C2—H2⋯O5iv	0.93	2.45	3.370 (2)	168
C9—H9A⋯O4iv	0.97	2.33	3.292 (2)	172
C6—H6⋯O8vi	0.93	2.46	3.273 (2)	147
C9—H9B⋯O2vii	0.97	2.37	3.324 (2)	167

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .