In the anion of the title salt, C
2H
6NO
2+·C
7H
5O
6S
−, the dihedral angle between the carboxylic 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 carboxylic acid groups and sulfonate O atoms. A pair of C—H

O interactions 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.
Supporting information
CCDC reference: 989106
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.049
- wR factor = 0.117
- Data-to-parameter ratio = 18.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.1 Note
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 5.033 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 7 Why ?
Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 10 Note
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do !
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 6 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 301 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
6 ALERT level G = General information/check it is not something unexpected
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
The title compound was obtained by slow evaporation from an aqueous solution
of glycine (C2H5NO2, 0.75 g) and 3-carboxy-4-hydroxybenzenesulfonic acid
(C7H6O6S, 2.18 g) at room temperature.
The good quality crystals suitable for X-ray diffraction
were collected in the period of 20 days.
H atoms of the NH3 and OH groups were located in a difference Fourier map and
refined freely, with bond-length restraints of N—H = 0.86 (1) Å and O—H =
0.82 (1) Å. The C-bound H atoms were positioned geometrically and refined
using a riding model, with C—H = 0.93 and Uiso(H) =
1.2Ueq(C) for CH and C—H = 0.97 Å and Uiso(H) =
1.2Ueq(C) for CH2.
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).
Glycinium 3-carboxy-4-hydroxybenzenesulfonate
top
Crystal data top
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 | |
Data collection top
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 top
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) |
Crystal data top
C2H6NO2+·C7H5O6S− | V = 1151.75 (12) Å3 |
Mr = 293.25 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.3651 (3) Å | µ = 0.32 mm−1 |
b = 24.7207 (15) Å | T = 295 K |
c = 8.6840 (5) Å | 0.36 × 0.32 × 0.30 mm |
β = 90.170 (2)° | |
Data collection top
Bruker Kappa APEXII CCD diffractometer | 3694 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3282 reflections with I > 2σ(I) |
Tmin = 0.893, Tmax = 0.910 | Rint = 0.030 |
21406 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.049 | 6 restraints |
wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.20 | Δρmax = 0.49 e Å−3 |
3694 reflections | Δρmin = −0.53 e Å−3 |
197 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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)* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) | | |
Hydrogen-bond geometry (Å, º) top
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) x−1, y, z; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+1, −y+1, −z+2; (iv) −x+2, −y+1, −z+2; (v) −x+2, −y+1, −z+1; (vi) −x+1, −y+1, −z+1; (vii) −x+2, y+1/2, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O6 | 0.823 (10) | 1.89 (2) | 2.631 (2) | 150 (4) |
N1—H1A···O6 | 0.863 (10) | 2.27 (3) | 2.878 (2) | 127 (3) |
N1—H1A···O7i | 0.863 (10) | 2.46 (3) | 3.134 (2) | 135 (3) |
N1—H1B···O3ii | 0.866 (10) | 2.061 (16) | 2.876 (2) | 157 (3) |
N1—H1C···O3iii | 0.865 (10) | 1.978 (15) | 2.811 (2) | 161 (3) |
O5—H5A···O4iv | 0.822 (10) | 1.917 (15) | 2.702 (2) | 159 (3) |
O7—H7···O2v | 0.821 (10) | 1.835 (12) | 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) x−1, y, z; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+1, −y+1, −z+2; (iv) −x+2, −y+1, −z+2; (v) −x+2, −y+1, −z+1; (vi) −x+1, −y+1, −z+1; (vii) −x+2, y+1/2, −z+3/2. |
Non-linear optical materials have recently invoked a large amount of interest due to their potential application in harmonic generation, optical information processing, optical storage and two photon pumped lasers (Yang et al., 2005; Kumar et al., 2009). We herein, report the crystal structure of the title compound (I), (Fig. 1). The geometric parameters of the title compound are comparable with the reported structures (Krishnakumar et al., 2012; Sudhahar et al., 2013).
In the molecular structure, the cation and anion are linked by N—H···O and O—H···O hydrogen bonds. In the anion, the dihedral angle between the carboxyl group and the benzene ring is 5.02 (12)°. The crystal structure exhibits intermolecular N—H···O, O—H···O and C—H···O (Table 1 & Fig. 2) interactions.