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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1798.
Published online 2008 August 20. doi: 10.1107/S1600536808026214.
PMCID: PMC2960710
Bis(carboxy­meth­yl)ammonium 4-toluene­sulfonate
Kong Mun Loa and Seik Weng Nga*
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng/at/um.edu.my
Received August 8, 2008; Accepted August 14, 2008.
Abstract
The imino­diacetic acid component of the title salt, C4H8NO4 +·C7H7SO3 , is protonated at the N atom. The cation uses the ammonium group to form hydrogen bonds to the O atoms of two adjacent sulfonate groups. In addition, the carboxylic acid portions of the cation form hydrogen bonds to the sulfonate groups. The hydrogen-bonding inter­actions give rise to a layer structure.
Related literature
For the crystal structures of imino­diacetic acid hydro­halides, see: Oskarsson (1973 [triangle], 1974a [triangle],b [triangle], 1976 [triangle]).
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Object name is e-64-o1798-scheme1.jpg Object name is e-64-o1798-scheme1.jpg
Crystal data
  • C4H8NO4 +·C7H7O3S
  • M r = 305.30
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1798-efi1.jpg
  • a = 9.9291 (2) Å
  • b = 10.3636 (2) Å
  • c = 25.8862 (5) Å
  • V = 2663.72 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 100 (2) K
  • 0.27 × 0.27 × 0.27 mm
Data collection
  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.929, T max = 0.929
  • 20842 measured reflections
  • 3059 independent reflections
  • 2560 reflections with I > 2σ(I)
  • R int = 0.048
Refinement
  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.119
  • S = 1.15
  • 3059 reflections
  • 198 parameters
  • 4 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.42 e Å−3
  • Δρmin = −0.50 e Å−3
Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026214/bh2187sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026214/bh2187Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
We thank the University of Malaya for funding this study (SF022/2007 A, FS339/2008 A) and also for the purchase of the diffractometer.
supplementary crystallographic information
Comment
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Experimental
Iminodiacetic acid (0.55 g, 4 mmol) and p-toluenesulfonic acid (0.65 g, 4 mmol) were heated in toluene (100 ml) for 1 h. Crystals were isolated from the cool solution after several days.
Refinement
Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 to 1.5Ueq(carrier C). The acid and ammonium H atoms were refined with distance restraints of O—H = 0.84 (1) and N—H = 0.88 (1) Å; their isotropic displacement parameters were freely refined.
Figures
Fig. 1.
Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of (C4H8NO4)+(C7H7O3S)- at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Crystal data
C4H8NO4+·C7H7O3SF000 = 1280
Mr = 305.30Dx = 1.523 Mg m3
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4293 reflections
a = 9.9291 (2) Åθ = 2.9–27.2º
b = 10.3636 (2) ŵ = 0.28 mm1
c = 25.8862 (5) ÅT = 100 (2) K
V = 2663.72 (9) Å3Triangular block, colorless
Z = 80.27 × 0.27 × 0.27 mm
Data collection
Bruker SMART APEX diffractometer3059 independent reflections
Radiation source: fine-focus sealed tube2560 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.048
T = 100(2) Kθmax = 27.5º
ω scansθmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −12→7
Tmin = 0.930, Tmax = 0.930k = −13→13
20842 measured reflectionsl = −33→33
Refinement
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119  w = 1/[σ2(Fo2) + (0.0644P)2 + 0.8206P] where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max = 0.001
3059 reflectionsΔρmax = 0.42 e Å3
198 parametersΔρmin = −0.50 e Å3
4 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
xyzUiso*/Ueq
S10.49041 (5)0.84948 (4)0.358654 (17)0.01248 (14)
O10.55419 (15)0.74172 (13)0.38508 (5)0.0195 (3)
O20.56209 (14)0.88382 (13)0.31102 (5)0.0163 (3)
O30.34727 (14)0.83294 (13)0.35029 (5)0.0190 (3)
O40.40223 (14)0.52637 (13)0.30853 (5)0.0171 (3)
O50.51261 (16)0.49339 (13)0.38301 (5)0.0199 (3)
H5O0.510 (3)0.5747 (10)0.3841 (10)0.034 (7)*
O60.20627 (14)0.17528 (13)0.21695 (5)0.0176 (3)
O70.29656 (14)−0.02406 (13)0.22217 (5)0.0163 (3)
H7O0.229 (2)−0.047 (3)0.2048 (10)0.051 (9)*
N10.37466 (17)0.27383 (15)0.28845 (6)0.0129 (3)
H1N10.402 (3)0.316 (2)0.2610 (7)0.031 (7)*
H1N20.2899 (11)0.296 (2)0.2924 (8)0.014 (5)*
C10.50864 (19)0.98391 (18)0.40013 (7)0.0141 (4)
C20.3995 (2)1.02980 (19)0.42797 (8)0.0187 (4)
H20.31460.98790.42560.022*
C30.4152 (2)1.1376 (2)0.45941 (8)0.0212 (4)
H30.34041.16810.47880.025*
C40.5374 (2)1.20164 (19)0.46306 (7)0.0183 (4)
C50.6471 (2)1.15329 (19)0.43556 (8)0.0191 (4)
H50.73191.19520.43800.023*
C60.6335 (2)1.04440 (19)0.40462 (7)0.0171 (4)
H60.70931.01120.38660.021*
C70.5517 (2)1.3217 (2)0.49545 (8)0.0247 (5)
H7A0.46361.36310.49930.037*
H7B0.61421.38150.47850.037*
H7C0.58681.29850.52960.037*
C80.45172 (19)0.45546 (18)0.34029 (7)0.0137 (4)
C90.45326 (19)0.31071 (18)0.33494 (7)0.0137 (4)
H9A0.54720.27980.33150.016*
H9B0.41320.27050.36600.016*
C100.3811 (2)0.13288 (17)0.27813 (7)0.0142 (4)
H10A0.35700.08450.30980.017*
H10B0.47380.10850.26800.017*
C110.28461 (19)0.09925 (18)0.23534 (7)0.0132 (4)
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
S10.0104 (2)0.0118 (2)0.0153 (2)−0.00084 (17)−0.00072 (16)0.00057 (16)
O10.0240 (8)0.0125 (7)0.0221 (7)−0.0013 (6)−0.0072 (6)0.0031 (5)
O20.0164 (7)0.0158 (7)0.0168 (7)−0.0021 (6)0.0028 (5)−0.0016 (5)
O30.0109 (7)0.0226 (8)0.0233 (7)−0.0016 (6)−0.0006 (6)−0.0024 (5)
O40.0169 (7)0.0148 (7)0.0197 (7)0.0007 (6)−0.0025 (5)0.0007 (5)
O50.0293 (9)0.0111 (7)0.0192 (7)−0.0007 (6)−0.0092 (6)−0.0014 (5)
O60.0156 (7)0.0155 (7)0.0217 (7)−0.0016 (6)−0.0030 (5)0.0033 (5)
O70.0134 (7)0.0143 (7)0.0211 (7)−0.0023 (6)−0.0006 (6)−0.0043 (5)
N10.0123 (8)0.0109 (8)0.0154 (8)0.0011 (6)−0.0002 (6)0.0000 (6)
C10.0144 (9)0.0131 (9)0.0149 (8)−0.0001 (7)−0.0003 (7)0.0010 (7)
C20.0148 (10)0.0198 (10)0.0215 (9)−0.0019 (8)0.0032 (8)0.0004 (8)
C30.0190 (11)0.0217 (10)0.0228 (10)0.0025 (8)0.0066 (8)−0.0020 (8)
C40.0237 (11)0.0162 (10)0.0150 (9)0.0007 (8)−0.0001 (8)0.0004 (7)
C50.0145 (10)0.0225 (10)0.0202 (9)−0.0045 (8)0.0002 (8)−0.0023 (8)
C60.0130 (9)0.0199 (10)0.0183 (9)0.0004 (8)0.0014 (7)−0.0027 (7)
C70.0276 (12)0.0219 (11)0.0247 (10)−0.0011 (9)0.0010 (9)−0.0067 (8)
C80.0102 (9)0.0150 (9)0.0161 (8)−0.0005 (7)0.0005 (7)0.0004 (7)
C90.0125 (9)0.0133 (9)0.0152 (9)0.0002 (7)−0.0026 (7)0.0000 (7)
C100.0132 (9)0.0095 (8)0.0200 (9)0.0004 (7)−0.0017 (7)−0.0009 (7)
C110.0108 (9)0.0132 (9)0.0157 (8)−0.0019 (7)0.0028 (7)0.0012 (7)
Geometric parameters (Å, °)
S1—O31.4478 (14)C2—H20.9500
S1—O11.4547 (14)C3—C41.386 (3)
S1—O21.4675 (13)C3—H30.9500
S1—C11.768 (2)C4—C51.394 (3)
O4—C81.207 (2)C4—C71.507 (3)
O5—C81.320 (2)C5—C61.390 (3)
O5—H5o0.84 (1)C5—H50.9500
O6—C111.205 (2)C6—H60.9500
O7—C111.328 (2)C7—H7A0.9800
O7—H7o0.84 (1)C7—H7B0.9800
N1—C91.484 (2)C7—H7C0.9800
N1—C101.486 (2)C8—C91.507 (3)
N1—H1n10.88 (1)C9—H9A0.9900
N1—H1n20.88 (1)C9—H9B0.9900
C1—C21.385 (3)C10—C111.505 (3)
C1—C61.394 (3)C10—H10A0.9900
C2—C31.391 (3)C10—H10B0.9900
O3—S1—O1114.00 (9)C4—C5—H5119.7
O3—S1—O2112.28 (8)C5—C6—C1119.93 (18)
O1—S1—O2111.72 (8)C5—C6—H6120.0
O3—S1—C1106.53 (9)C1—C6—H6120.0
O1—S1—C1105.95 (9)C4—C7—H7A109.5
O2—S1—C1105.63 (8)C4—C7—H7B109.5
C8—O5—H5O108.2 (18)H7A—C7—H7B109.5
C11—O7—H7O110 (2)C4—C7—H7C109.5
C9—N1—C10112.10 (14)H7A—C7—H7C109.5
C9—N1—H1N1111.7 (17)H7B—C7—H7C109.5
C10—N1—H1N1109.4 (16)O4—C8—O5125.13 (18)
C9—N1—H1N2110.2 (14)O4—C8—C9123.20 (17)
C10—N1—H1N2108.3 (15)O5—C8—C9111.66 (15)
H1N1—N1—H1N2105 (2)N1—C9—C8109.01 (15)
C2—C1—C6119.85 (18)N1—C9—H9A109.9
C2—C1—S1120.41 (15)C8—C9—H9A109.9
C6—C1—S1119.73 (15)N1—C9—H9B109.9
C1—C2—C3119.53 (19)C8—C9—H9B109.9
C1—C2—H2120.2H9A—C9—H9B108.3
C3—C2—H2120.2N1—C10—C11109.43 (15)
C4—C3—C2121.46 (18)N1—C10—H10A109.8
C4—C3—H3119.3C11—C10—H10A109.8
C2—C3—H3119.3N1—C10—H10B109.8
C3—C4—C5118.49 (18)C11—C10—H10B109.8
C3—C4—C7121.06 (19)H10A—C10—H10B108.2
C5—C4—C7120.4 (2)O6—C11—O7125.83 (17)
C6—C5—C4120.68 (19)O6—C11—C10123.36 (17)
C6—C5—H5119.7O7—C11—C10110.79 (16)
O3—S1—C1—C216.35 (19)C3—C4—C5—C60.9 (3)
O1—S1—C1—C2−105.40 (17)C7—C4—C5—C6−178.42 (18)
O2—S1—C1—C2135.94 (16)C4—C5—C6—C11.2 (3)
O3—S1—C1—C6−163.36 (15)C2—C1—C6—C5−2.3 (3)
O1—S1—C1—C674.89 (17)S1—C1—C6—C5177.39 (15)
O2—S1—C1—C6−43.77 (18)C10—N1—C9—C8175.26 (15)
C6—C1—C2—C31.3 (3)O4—C8—C9—N1−5.4 (3)
S1—C1—C2—C3−178.42 (15)O5—C8—C9—N1175.76 (15)
C1—C2—C3—C40.9 (3)C9—N1—C10—C11172.17 (15)
C2—C3—C4—C5−1.9 (3)N1—C10—C11—O6−6.8 (3)
C2—C3—C4—C7177.37 (19)N1—C10—C11—O7174.56 (14)
Hydrogen-bond geometry (Å, °)
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O2i0.88 (1)2.02 (1)2.885 (2)167 (2)
N1—H1N2···O3ii0.88 (1)2.06 (2)2.792 (2)140 (2)
O5—H5O···O10.84 (1)1.79 (1)2.607 (2)164 (3)
O7—H7O···O2iii0.84 (1)1.85 (1)2.659 (2)160 (3)
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1/2, y−1/2, z; (iii) x−1/2, y−1, −z+1/2.
 
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2187).
References
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  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Oskarsson, Å. (1973). Acta Cryst. B29, 1747–1751.
  • Oskarsson, Å. (1974a). Acta Cryst. B30, 780–783.
  • Oskarsson, Å. (1974b). Acta Cryst. B30, 1184–1188.
  • Oskarsson, A. (1976). Acta Cryst. B32, 2163–2170.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
  • Westrip, S. P. (2008). publCIF In preparation.

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