organic compounds
2,6-Diaminotoluene-4-sulfonic acid exists in the zwitterionic form as 2-amino-6-ammoniotoluene-4-sulfonate, C7H10N2O3S; the molecule features a C-Namino bond [1.372 (3) Å] which is significantly shorter than the C-Nammonio bond [1.473 (3) Å]. Neighbouring molecules are linked by extensive hydrogen bonds into a three-dimensional network structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032234/kp6024sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032234/kp6024Isup2.hkl |
CCDC reference: 262460
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.045
- wR factor = 0.115
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.90 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.89 Ratio PLAT391_ALERT_3_C Deviating Methyl C7 H-C-H Bond Angle ...... 101.00 Deg. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 5 PLAT731_ALERT_1_C Bond Calc 0.84(3), Rep 0.850(10) ...... 3.00 su-Rat N1 -H1N2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat N2 -H2N1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.86(3), Rep 0.860(10) ...... 3.00 su-Rat N2 -H2N3 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(3), Rep 0.850(10) ...... 3.00 su-Rat N1 -H2# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat N2 -H3# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(3), Rep 0.860(10) ...... 3.00 su-Rat N2 -H5# 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.96(3), Rep 1.960(10) ...... 3.00 su-Rat H5# -O2 1.555 3.566
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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
Computing details top
Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku Corporation, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
2-amino-6-ammoniotoluene-4-sulfonate top
Crystal data top
C7H10N2O3S | F(000) = 424 |
Mr = 202.23 | Dx = 1.523 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7571 reflections |
a = 8.420 (2) Å | θ = 3.1–27.5° |
b = 13.087 (3) Å | µ = 0.34 mm−1 |
c = 8.938 (2) Å | T = 295 K |
β = 116.45 (3)° | Block, colorless |
V = 881.7 (3) Å3 | 0.38 × 0.24 × 0.10 mm |
Z = 4 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2010 independent reflections |
Radiation source: fine-focus sealed tube | 1459 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
ω scan | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −10→10 |
Tmin = 0.790, Tmax = 0.967 | k = −16→16 |
8538 measured reflections | l = −11→10 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | All H-atom parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0555P)2 + 0.3519P] where P = (Fo2 + 2Fc2)/3 |
2010 reflections | (Δ/σ)max = 0.001 |
158 parameters | Δρmax = 0.40 e Å−3 |
10 restraints | Δρmin = −0.34 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.19936 (9) | 0.63625 (4) | 0.84490 (7) | 0.0226 (2) | |
O1 | 0.3693 (3) | 0.6815 (1) | 0.9522 (2) | 0.0331 (5) | |
O2 | 0.1441 (3) | 0.5633 (1) | 0.9364 (2) | 0.0314 (4) | |
O3 | 0.0634 (3) | 0.7112 (1) | 0.7535 (2) | 0.0318 (4) | |
N1 | 0.4824 (4) | 0.3399 (2) | 0.6817 (3) | 0.0486 (7) | |
N2 | 0.1209 (3) | 0.5796 (2) | 0.2445 (3) | 0.0276 (5) | |
C1 | 0.2308 (3) | 0.5641 (2) | 0.6930 (3) | 0.0227 (5) | |
C2 | 0.3326 (4) | 0.4765 (2) | 0.7422 (3) | 0.0277 (6) | |
C3 | 0.3679 (4) | 0.4212 (2) | 0.6266 (3) | 0.0276 (5) | |
C4 | 0.2938 (3) | 0.4520 (2) | 0.4578 (3) | 0.0249 (5) | |
C5 | 0.1959 (3) | 0.5418 (2) | 0.4177 (3) | 0.0231 (5) | |
C6 | 0.1602 (3) | 0.5984 (2) | 0.5296 (3) | 0.0224 (5) | |
C7 | 0.3264 (4) | 0.3896 (2) | 0.3331 (3) | 0.0330 (6) | |
H1n1 | 0.513 (5) | 0.323 (3) | 0.7824 (19) | 0.06 (1)* | |
H1n2 | 0.489 (4) | 0.299 (2) | 0.612 (3) | 0.03 (1)* | |
H2n1 | 0.196 (3) | 0.576 (3) | 0.205 (4) | 0.05 (1)* | |
H2n2 | 0.093 (4) | 0.643 (1) | 0.245 (4) | 0.04 (1)* | |
H2n3 | 0.031 (3) | 0.543 (2) | 0.183 (3) | 0.04 (1)* | |
H2 | 0.388 (3) | 0.454 (2) | 0.856 (2) | 0.018 (6)* | |
H6 | 0.095 (3) | 0.660 (1) | 0.500 (3) | 0.029 (7)* | |
H7a | 0.269 (5) | 0.414 (3) | 0.222 (2) | 0.07 (1)* | |
H7b | 0.273 (4) | 0.324 (1) | 0.320 (4) | 0.06 (1)* | |
H7c | 0.449 (2) | 0.381 (2) | 0.363 (4) | 0.04 (1)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0326 (3) | 0.0207 (3) | 0.0192 (3) | −0.0031 (2) | 0.0157 (2) | −0.0023 (2) |
O1 | 0.039 (1) | 0.034 (1) | 0.025 (1) | −0.012 (1) | 0.013 (1) | −0.005 (1) |
O2 | 0.050 (1) | 0.029 (1) | 0.025 (1) | −0.010 (1) | 0.026 (1) | −0.005 (1) |
O3 | 0.040 (1) | 0.028 (1) | 0.030 (1) | 0.006 (1) | 0.018 (1) | −0.002 (1) |
N1 | 0.075 (2) | 0.045 (2) | 0.030 (1) | 0.031 (1) | 0.027 (1) | 0.007 (1) |
N2 | 0.039 (1) | 0.027 (1) | 0.020 (1) | −0.001 (1) | 0.016 (1) | −0.001 (1) |
C1 | 0.029 (1) | 0.023 (1) | 0.021 (1) | −0.003 (1) | 0.016 (1) | −0.003 (1) |
C2 | 0.038 (2) | 0.028 (1) | 0.020 (1) | 0.004 (1) | 0.016 (1) | 0.003 (1) |
C3 | 0.033 (1) | 0.027 (1) | 0.026 (1) | 0.005 (1) | 0.016 (1) | 0.003 (1) |
C4 | 0.031 (1) | 0.026 (1) | 0.023 (1) | −0.003 (1) | 0.017 (1) | −0.005 (1) |
C5 | 0.027 (1) | 0.028 (1) | 0.016 (1) | −0.003 (1) | 0.011 (1) | 0.002 (1) |
C6 | 0.030 (1) | 0.021 (1) | 0.021 (1) | −0.002 (1) | 0.015 (1) | 0.000 (1) |
C7 | 0.037 (2) | 0.037 (1) | 0.030 (1) | 0.004 (1) | 0.019 (1) | −0.006 (1) |
Geometric parameters (Å, º) top
S1—O1 | 1.447 (2) | C5—C6 | 1.382 (3) |
S1—O2 | 1.462 (2) | N1—H1n1 | 0.85 (1) |
S1—O3 | 1.451 (2) | N1—H1n2 | 0.85 (1) |
S1—C1 | 1.767 (2) | N2—H2n1 | 0.85 (1) |
N1—C3 | 1.372 (3) | N2—H2n2 | 0.86 (1) |
N2—C5 | 1.473 (3) | N2—H2n3 | 0.86 (1) |
C1—C2 | 1.381 (3) | C2—H2 | 0.96 (1) |
C1—C6 | 1.383 (3) | C6—H6 | 0.94 (1) |
C2—C3 | 1.397 (3) | C7—H7a | 0.94 (1) |
C3—C4 | 1.410 (3) | C7—H7b | 0.95 (1) |
C4—C5 | 1.387 (3) | C7—H7c | 0.95 (1) |
C4—C7 | 1.503 (3) | ||
O1—S1—O2 | 111.3 (1) | C3—N1—H1n1 | 115 (3) |
O1—S1—O3 | 113.3 (1) | C3—N1—H1n2 | 120 (2) |
O2—S1—O3 | 112.9 (1) | H1n1—N1—H1n2 | 122 (3) |
O1—S1—C1 | 106.6 (1) | C5—N2—H2n1 | 112 (2) |
O2—S1—C1 | 106.0 (1) | C5—N2—H2n2 | 108 (2) |
O3—S1—C1 | 106.2 (1) | H2n1—N2—H2n2 | 108 (3) |
C2—C1—C6 | 121.3 (2) | C5—N2—H2n3 | 110 (2) |
C2—C1—S1 | 118.9 (2) | H2n1—N2—H2n3 | 108 (3) |
C6—C1—S1 | 119.8 (2) | H2n2—N2—H2n3 | 112 (3) |
C1—C2—C3 | 120.0 (2) | C1—C2—H2 | 123 (2) |
N1—C3—C2 | 118.9 (2) | C3—C2—H2 | 117 (2) |
N1—C3—C4 | 120.7 (2) | C5—C6—H6 | 123 (2) |
C2—C3—C4 | 120.3 (2) | C1—C6—H6 | 120 (2) |
C3—C4—C5 | 116.6 (2) | C4—C7—H7a | 115 (2) |
C3—C4—C7 | 119.9 (2) | C4—C7—H7b | 111 (2) |
C5—C4—C7 | 123.5 (2) | H7a—C7—H7b | 100 (3) |
C4—C5—C6 | 124.2 (2) | C4—C7—H7c | 113 (2) |
C4—C5—N2 | 118.9 (2) | H7a—C7—H7c | 109 (3) |
C6—C5—N2 | 116.8 (2) | H7b—C7—H7c | 108 (3) |
C1—C6—C5 | 117.4 (2) | ||
O1—S1—C1—C2 | 69.1 (2) | C2—C3—C4—C5 | 3.9 (4) |
O3—S1—C1—C2 | −169.8 (2) | N1—C3—C4—C7 | 5.8 (4) |
O2—S1—C1—C2 | −49.6 (2) | C2—C3—C4—C7 | −177.5 (2) |
O1—S1—C1—C6 | −108.1 (2) | C3—C4—C5—C6 | −3.5 (4) |
O3—S1—C1—C6 | 13.0 (2) | C7—C4—C5—C6 | 178.0 (2) |
O2—S1—C1—C6 | 133.3 (2) | C3—C4—C5—N2 | 177.8 (2) |
C6—C1—C2—C3 | 0.8 (4) | C7—C4—C5—N2 | −0.7 (4) |
S1—C1—C2—C3 | −176.4 (2) | C4—C5—C6—C1 | 1.7 (4) |
C1—C2—C3—N1 | 174.1 (3) | N2—C5—C6—C1 | −179.6 (2) |
C1—C2—C3—C4 | −2.7 (4) | C2—C1—C6—C5 | −0.2 (4) |
N1—C3—C4—C5 | −172.8 (3) | S1—C1—C6—C5 | 176.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n1···O1i | 0.85 (1) | 2.13 (1) | 2.950 (3) | 164 (3) |
N1—H1n2···O1ii | 0.85 (1) | 2.17 (2) | 2.936 (3) | 150 (2) |
N2—H2n1···O2iii | 0.85 (1) | 2.25 (3) | 2.854 (3) | 128 (3) |
N2—H2n2···O3iv | 0.86 (1) | 1.94 (1) | 2.788 (3) | 173 (3) |
N2—H2n3···O2v | 0.86 (1) | 1.96 (1) | 2.806 (3) | 168 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, y−1/2, −z+3/2; (iii) x, y, z−1; (iv) x, −y+3/2, z−1/2; (v) −x, −y+1, −z+1. |