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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1798. | PMCID: PMC2960710 |
Bis(carboxymethyl)ammonium 4-toluenesulfonate Kong Mun Loa and Seik Weng Nga* aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia Received August 8, 2008; Accepted August 14, 2008. This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. 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. For the crystal structures of iminodiacetic acid hydrohalides, see: Oskarsson (1973 ![[triangle]](/corehtml/pmc/pmcents/rtrif.gif) , 1974 a
, b
, 1976 ). Click on image to enlarge  Crystal data
- C4H8NO4
+·C7H7O3S−
-
M
r = 305.30
- Orthorhombic,
-
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 ) 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 ); 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).
| Table 1Hydrogen-bond geometry (Å, °) |
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
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. Crystal data | C4H8NO4+·C7H7O3S– | F000 = 1280 | | Mr = 305.30 | Dx = 1.523 Mg m−3 | | Orthorhombic, Pbca | Mo Kα radiation λ = 0.71073 Å | | Hall symbol: -P 2ac 2ab | Cell parameters from 4293 reflections | | a = 9.9291 (2) Å | θ = 2.9–27.2º | | b = 10.3636 (2) Å | µ = 0.28 mm−1 | | c = 25.8862 (5) Å | T = 100 (2) K | | V = 2663.72 (9) Å3 | Triangular block, colorless | | Z = 8 | 0.27 × 0.27 × 0.27 mm |
Data collection | Bruker SMART APEX diffractometer | 3059 independent reflections | | Radiation source: fine-focus sealed tube | 2560 reflections with I > 2σ(I) | | Monochromator: graphite | Rint = 0.048 | | T = 100(2) K | θmax = 27.5º | | ω scans | θmin = 1.6º | | Absorption correction: multi-scan(SADABS; Sheldrick, 1996) | h = −12→7 | | Tmin = 0.930, Tmax = 0.930 | k = −13→13 | | 20842 measured reflections | l = −33→33 |
Refinement | 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)] = 0.038 | H 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 reflections | Δρmax = 0.42 e Å−3 | | 198 parameters | Δρmin = −0.50 e Å−3 | | 4 restraints | Extinction correction: none | | Primary atom site location: structure-invariant direct methods | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) | x | y | z | Uiso*/Ueq | | | S1 | 0.49041 (5) | 0.84948 (4) | 0.358654 (17) | 0.01248 (14) | | | O1 | 0.55419 (15) | 0.74172 (13) | 0.38508 (5) | 0.0195 (3) | | | O2 | 0.56209 (14) | 0.88382 (13) | 0.31102 (5) | 0.0163 (3) | | | O3 | 0.34727 (14) | 0.83294 (13) | 0.35029 (5) | 0.0190 (3) | | | O4 | 0.40223 (14) | 0.52637 (13) | 0.30853 (5) | 0.0171 (3) | | | O5 | 0.51261 (16) | 0.49339 (13) | 0.38301 (5) | 0.0199 (3) | | | H5O | 0.510 (3) | 0.5747 (10) | 0.3841 (10) | 0.034 (7)* | | | O6 | 0.20627 (14) | 0.17528 (13) | 0.21695 (5) | 0.0176 (3) | | | O7 | 0.29656 (14) | −0.02406 (13) | 0.22217 (5) | 0.0163 (3) | | | H7O | 0.229 (2) | −0.047 (3) | 0.2048 (10) | 0.051 (9)* | | | N1 | 0.37466 (17) | 0.27383 (15) | 0.28845 (6) | 0.0129 (3) | | | H1N1 | 0.402 (3) | 0.316 (2) | 0.2610 (7) | 0.031 (7)* | | | H1N2 | 0.2899 (11) | 0.296 (2) | 0.2924 (8) | 0.014 (5)* | | | C1 | 0.50864 (19) | 0.98391 (18) | 0.40013 (7) | 0.0141 (4) | | | C2 | 0.3995 (2) | 1.02980 (19) | 0.42797 (8) | 0.0187 (4) | | | H2 | 0.3146 | 0.9879 | 0.4256 | 0.022* | | | C3 | 0.4152 (2) | 1.1376 (2) | 0.45941 (8) | 0.0212 (4) | | | H3 | 0.3404 | 1.1681 | 0.4788 | 0.025* | | | C4 | 0.5374 (2) | 1.20164 (19) | 0.46306 (7) | 0.0183 (4) | | | C5 | 0.6471 (2) | 1.15329 (19) | 0.43556 (8) | 0.0191 (4) | | | H5 | 0.7319 | 1.1952 | 0.4380 | 0.023* | | | C6 | 0.6335 (2) | 1.04440 (19) | 0.40462 (7) | 0.0171 (4) | | | H6 | 0.7093 | 1.0112 | 0.3866 | 0.021* | | | C7 | 0.5517 (2) | 1.3217 (2) | 0.49545 (8) | 0.0247 (5) | | | H7A | 0.4636 | 1.3631 | 0.4993 | 0.037* | | | H7B | 0.6142 | 1.3815 | 0.4785 | 0.037* | | | H7C | 0.5868 | 1.2985 | 0.5296 | 0.037* | | | C8 | 0.45172 (19) | 0.45546 (18) | 0.34029 (7) | 0.0137 (4) | | | C9 | 0.45326 (19) | 0.31071 (18) | 0.33494 (7) | 0.0137 (4) | | | H9A | 0.5472 | 0.2798 | 0.3315 | 0.016* | | | H9B | 0.4132 | 0.2705 | 0.3660 | 0.016* | | | C10 | 0.3811 (2) | 0.13288 (17) | 0.27813 (7) | 0.0142 (4) | | | H10A | 0.3570 | 0.0845 | 0.3098 | 0.017* | | | H10B | 0.4738 | 0.1085 | 0.2680 | 0.017* | | | C11 | 0.28461 (19) | 0.09925 (18) | 0.23534 (7) | 0.0132 (4) | |
Atomic displacement parameters (Å2) | U11 | U22 | U33 | U12 | U13 | U23 | | S1 | 0.0104 (2) | 0.0118 (2) | 0.0153 (2) | −0.00084 (17) | −0.00072 (16) | 0.00057 (16) | | O1 | 0.0240 (8) | 0.0125 (7) | 0.0221 (7) | −0.0013 (6) | −0.0072 (6) | 0.0031 (5) | | O2 | 0.0164 (7) | 0.0158 (7) | 0.0168 (7) | −0.0021 (6) | 0.0028 (5) | −0.0016 (5) | | O3 | 0.0109 (7) | 0.0226 (8) | 0.0233 (7) | −0.0016 (6) | −0.0006 (6) | −0.0024 (5) | | O4 | 0.0169 (7) | 0.0148 (7) | 0.0197 (7) | 0.0007 (6) | −0.0025 (5) | 0.0007 (5) | | O5 | 0.0293 (9) | 0.0111 (7) | 0.0192 (7) | −0.0007 (6) | −0.0092 (6) | −0.0014 (5) | | O6 | 0.0156 (7) | 0.0155 (7) | 0.0217 (7) | −0.0016 (6) | −0.0030 (5) | 0.0033 (5) | | O7 | 0.0134 (7) | 0.0143 (7) | 0.0211 (7) | −0.0023 (6) | −0.0006 (6) | −0.0043 (5) | | N1 | 0.0123 (8) | 0.0109 (8) | 0.0154 (8) | 0.0011 (6) | −0.0002 (6) | 0.0000 (6) | | C1 | 0.0144 (9) | 0.0131 (9) | 0.0149 (8) | −0.0001 (7) | −0.0003 (7) | 0.0010 (7) | | C2 | 0.0148 (10) | 0.0198 (10) | 0.0215 (9) | −0.0019 (8) | 0.0032 (8) | 0.0004 (8) | | C3 | 0.0190 (11) | 0.0217 (10) | 0.0228 (10) | 0.0025 (8) | 0.0066 (8) | −0.0020 (8) | | C4 | 0.0237 (11) | 0.0162 (10) | 0.0150 (9) | 0.0007 (8) | −0.0001 (8) | 0.0004 (7) | | C5 | 0.0145 (10) | 0.0225 (10) | 0.0202 (9) | −0.0045 (8) | 0.0002 (8) | −0.0023 (8) | | C6 | 0.0130 (9) | 0.0199 (10) | 0.0183 (9) | 0.0004 (8) | 0.0014 (7) | −0.0027 (7) | | C7 | 0.0276 (12) | 0.0219 (11) | 0.0247 (10) | −0.0011 (9) | 0.0010 (9) | −0.0067 (8) | | C8 | 0.0102 (9) | 0.0150 (9) | 0.0161 (8) | −0.0005 (7) | 0.0005 (7) | 0.0004 (7) | | C9 | 0.0125 (9) | 0.0133 (9) | 0.0152 (9) | 0.0002 (7) | −0.0026 (7) | 0.0000 (7) | | C10 | 0.0132 (9) | 0.0095 (8) | 0.0200 (9) | 0.0004 (7) | −0.0017 (7) | −0.0009 (7) | | C11 | 0.0108 (9) | 0.0132 (9) | 0.0157 (8) | −0.0019 (7) | 0.0028 (7) | 0.0012 (7) |
Geometric parameters (Å, °) | S1—O3 | 1.4478 (14) | C2—H2 | 0.9500 | | S1—O1 | 1.4547 (14) | C3—C4 | 1.386 (3) | | S1—O2 | 1.4675 (13) | C3—H3 | 0.9500 | | S1—C1 | 1.768 (2) | C4—C5 | 1.394 (3) | | O4—C8 | 1.207 (2) | C4—C7 | 1.507 (3) | | O5—C8 | 1.320 (2) | C5—C6 | 1.390 (3) | | O5—H5o | 0.84 (1) | C5—H5 | 0.9500 | | O6—C11 | 1.205 (2) | C6—H6 | 0.9500 | | O7—C11 | 1.328 (2) | C7—H7A | 0.9800 | | O7—H7o | 0.84 (1) | C7—H7B | 0.9800 | | N1—C9 | 1.484 (2) | C7—H7C | 0.9800 | | N1—C10 | 1.486 (2) | C8—C9 | 1.507 (3) | | N1—H1n1 | 0.88 (1) | C9—H9A | 0.9900 | | N1—H1n2 | 0.88 (1) | C9—H9B | 0.9900 | | C1—C2 | 1.385 (3) | C10—C11 | 1.505 (3) | | C1—C6 | 1.394 (3) | C10—H10A | 0.9900 | | C2—C3 | 1.391 (3) | C10—H10B | 0.9900 | | | | | | O3—S1—O1 | 114.00 (9) | C4—C5—H5 | 119.7 | | O3—S1—O2 | 112.28 (8) | C5—C6—C1 | 119.93 (18) | | O1—S1—O2 | 111.72 (8) | C5—C6—H6 | 120.0 | | O3—S1—C1 | 106.53 (9) | C1—C6—H6 | 120.0 | | O1—S1—C1 | 105.95 (9) | C4—C7—H7A | 109.5 | | O2—S1—C1 | 105.63 (8) | C4—C7—H7B | 109.5 | | C8—O5—H5O | 108.2 (18) | H7A—C7—H7B | 109.5 | | C11—O7—H7O | 110 (2) | C4—C7—H7C | 109.5 | | C9—N1—C10 | 112.10 (14) | H7A—C7—H7C | 109.5 | | C9—N1—H1N1 | 111.7 (17) | H7B—C7—H7C | 109.5 | | C10—N1—H1N1 | 109.4 (16) | O4—C8—O5 | 125.13 (18) | | C9—N1—H1N2 | 110.2 (14) | O4—C8—C9 | 123.20 (17) | | C10—N1—H1N2 | 108.3 (15) | O5—C8—C9 | 111.66 (15) | | H1N1—N1—H1N2 | 105 (2) | N1—C9—C8 | 109.01 (15) | | C2—C1—C6 | 119.85 (18) | N1—C9—H9A | 109.9 | | C2—C1—S1 | 120.41 (15) | C8—C9—H9A | 109.9 | | C6—C1—S1 | 119.73 (15) | N1—C9—H9B | 109.9 | | C1—C2—C3 | 119.53 (19) | C8—C9—H9B | 109.9 | | C1—C2—H2 | 120.2 | H9A—C9—H9B | 108.3 | | C3—C2—H2 | 120.2 | N1—C10—C11 | 109.43 (15) | | C4—C3—C2 | 121.46 (18) | N1—C10—H10A | 109.8 | | C4—C3—H3 | 119.3 | C11—C10—H10A | 109.8 | | C2—C3—H3 | 119.3 | N1—C10—H10B | 109.8 | | C3—C4—C5 | 118.49 (18) | C11—C10—H10B | 109.8 | | C3—C4—C7 | 121.06 (19) | H10A—C10—H10B | 108.2 | | C5—C4—C7 | 120.4 (2) | O6—C11—O7 | 125.83 (17) | | C6—C5—C4 | 120.68 (19) | O6—C11—C10 | 123.36 (17) | | C6—C5—H5 | 119.7 | O7—C11—C10 | 110.79 (16) | | | | | | O3—S1—C1—C2 | 16.35 (19) | C3—C4—C5—C6 | 0.9 (3) | | O1—S1—C1—C2 | −105.40 (17) | C7—C4—C5—C6 | −178.42 (18) | | O2—S1—C1—C2 | 135.94 (16) | C4—C5—C6—C1 | 1.2 (3) | | O3—S1—C1—C6 | −163.36 (15) | C2—C1—C6—C5 | −2.3 (3) | | O1—S1—C1—C6 | 74.89 (17) | S1—C1—C6—C5 | 177.39 (15) | | O2—S1—C1—C6 | −43.77 (18) | C10—N1—C9—C8 | 175.26 (15) | | C6—C1—C2—C3 | 1.3 (3) | O4—C8—C9—N1 | −5.4 (3) | | S1—C1—C2—C3 | −178.42 (15) | O5—C8—C9—N1 | 175.76 (15) | | C1—C2—C3—C4 | 0.9 (3) | C9—N1—C10—C11 | 172.17 (15) | | C2—C3—C4—C5 | −1.9 (3) | N1—C10—C11—O6 | −6.8 (3) | | C2—C3—C4—C7 | 177.37 (19) | N1—C10—C11—O7 | 174.56 (14) |
Hydrogen-bond geometry (Å, °) | D—H···A | D—H | H···A | D···A | D—H···A | | N1—H1N1···O2i | 0.88 (1) | 2.02 (1) | 2.885 (2) | 167 (2) | | N1—H1N2···O3ii | 0.88 (1) | 2.06 (2) | 2.792 (2) | 140 (2) | | O5—H5O···O1 | 0.84 (1) | 1.79 (1) | 2.607 (2) | 164 (3) | | O7—H7O···O2iii | 0.84 (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. - Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
- 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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