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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032234/kp6024sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032234/kp6024Isup2.hkl
Contains datablock I

CCDC reference: 262460

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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
C7H10N2O3SF(000) = 424
Mr = 202.23Dx = 1.523 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7571 reflections
a = 8.420 (2) Åθ = 3.1–27.5°
b = 13.087 (3) ŵ = 0.34 mm1
c = 8.938 (2) ÅT = 295 K
β = 116.45 (3)°Block, colorless
V = 881.7 (3) Å30.38 × 0.24 × 0.10 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2010 independent reflections
Radiation source: fine-focus sealed tube1459 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
ω scanθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1010
Tmin = 0.790, Tmax = 0.967k = 1616
8538 measured reflectionsl = 1110
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115All 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 parametersΔρmax = 0.40 e Å3
10 restraintsΔρmin = 0.34 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.19936 (9)0.63625 (4)0.84490 (7)0.0226 (2)
O10.3693 (3)0.6815 (1)0.9522 (2)0.0331 (5)
O20.1441 (3)0.5633 (1)0.9364 (2)0.0314 (4)
O30.0634 (3)0.7112 (1)0.7535 (2)0.0318 (4)
N10.4824 (4)0.3399 (2)0.6817 (3)0.0486 (7)
N20.1209 (3)0.5796 (2)0.2445 (3)0.0276 (5)
C10.2308 (3)0.5641 (2)0.6930 (3)0.0227 (5)
C20.3326 (4)0.4765 (2)0.7422 (3)0.0277 (6)
C30.3679 (4)0.4212 (2)0.6266 (3)0.0276 (5)
C40.2938 (3)0.4520 (2)0.4578 (3)0.0249 (5)
C50.1959 (3)0.5418 (2)0.4177 (3)0.0231 (5)
C60.1602 (3)0.5984 (2)0.5296 (3)0.0224 (5)
C70.3264 (4)0.3896 (2)0.3331 (3)0.0330 (6)
H1n10.513 (5)0.323 (3)0.7824 (19)0.06 (1)*
H1n20.489 (4)0.299 (2)0.612 (3)0.03 (1)*
H2n10.196 (3)0.576 (3)0.205 (4)0.05 (1)*
H2n20.093 (4)0.643 (1)0.245 (4)0.04 (1)*
H2n30.031 (3)0.543 (2)0.183 (3)0.04 (1)*
H20.388 (3)0.454 (2)0.856 (2)0.018 (6)*
H60.095 (3)0.660 (1)0.500 (3)0.029 (7)*
H7a0.269 (5)0.414 (3)0.222 (2)0.07 (1)*
H7b0.273 (4)0.324 (1)0.320 (4)0.06 (1)*
H7c0.449 (2)0.381 (2)0.363 (4)0.04 (1)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0326 (3)0.0207 (3)0.0192 (3)0.0031 (2)0.0157 (2)0.0023 (2)
O10.039 (1)0.034 (1)0.025 (1)0.012 (1)0.013 (1)0.005 (1)
O20.050 (1)0.029 (1)0.025 (1)0.010 (1)0.026 (1)0.005 (1)
O30.040 (1)0.028 (1)0.030 (1)0.006 (1)0.018 (1)0.002 (1)
N10.075 (2)0.045 (2)0.030 (1)0.031 (1)0.027 (1)0.007 (1)
N20.039 (1)0.027 (1)0.020 (1)0.001 (1)0.016 (1)0.001 (1)
C10.029 (1)0.023 (1)0.021 (1)0.003 (1)0.016 (1)0.003 (1)
C20.038 (2)0.028 (1)0.020 (1)0.004 (1)0.016 (1)0.003 (1)
C30.033 (1)0.027 (1)0.026 (1)0.005 (1)0.016 (1)0.003 (1)
C40.031 (1)0.026 (1)0.023 (1)0.003 (1)0.017 (1)0.005 (1)
C50.027 (1)0.028 (1)0.016 (1)0.003 (1)0.011 (1)0.002 (1)
C60.030 (1)0.021 (1)0.021 (1)0.002 (1)0.015 (1)0.000 (1)
C70.037 (2)0.037 (1)0.030 (1)0.004 (1)0.019 (1)0.006 (1)
Geometric parameters (Å, º) top
S1—O11.447 (2)C5—C61.382 (3)
S1—O21.462 (2)N1—H1n10.85 (1)
S1—O31.451 (2)N1—H1n20.85 (1)
S1—C11.767 (2)N2—H2n10.85 (1)
N1—C31.372 (3)N2—H2n20.86 (1)
N2—C51.473 (3)N2—H2n30.86 (1)
C1—C21.381 (3)C2—H20.96 (1)
C1—C61.383 (3)C6—H60.94 (1)
C2—C31.397 (3)C7—H7a0.94 (1)
C3—C41.410 (3)C7—H7b0.95 (1)
C4—C51.387 (3)C7—H7c0.95 (1)
C4—C71.503 (3)
O1—S1—O2111.3 (1)C3—N1—H1n1115 (3)
O1—S1—O3113.3 (1)C3—N1—H1n2120 (2)
O2—S1—O3112.9 (1)H1n1—N1—H1n2122 (3)
O1—S1—C1106.6 (1)C5—N2—H2n1112 (2)
O2—S1—C1106.0 (1)C5—N2—H2n2108 (2)
O3—S1—C1106.2 (1)H2n1—N2—H2n2108 (3)
C2—C1—C6121.3 (2)C5—N2—H2n3110 (2)
C2—C1—S1118.9 (2)H2n1—N2—H2n3108 (3)
C6—C1—S1119.8 (2)H2n2—N2—H2n3112 (3)
C1—C2—C3120.0 (2)C1—C2—H2123 (2)
N1—C3—C2118.9 (2)C3—C2—H2117 (2)
N1—C3—C4120.7 (2)C5—C6—H6123 (2)
C2—C3—C4120.3 (2)C1—C6—H6120 (2)
C3—C4—C5116.6 (2)C4—C7—H7a115 (2)
C3—C4—C7119.9 (2)C4—C7—H7b111 (2)
C5—C4—C7123.5 (2)H7a—C7—H7b100 (3)
C4—C5—C6124.2 (2)C4—C7—H7c113 (2)
C4—C5—N2118.9 (2)H7a—C7—H7c109 (3)
C6—C5—N2116.8 (2)H7b—C7—H7c108 (3)
C1—C6—C5117.4 (2)
O1—S1—C1—C269.1 (2)C2—C3—C4—C53.9 (4)
O3—S1—C1—C2169.8 (2)N1—C3—C4—C75.8 (4)
O2—S1—C1—C249.6 (2)C2—C3—C4—C7177.5 (2)
O1—S1—C1—C6108.1 (2)C3—C4—C5—C63.5 (4)
O3—S1—C1—C613.0 (2)C7—C4—C5—C6178.0 (2)
O2—S1—C1—C6133.3 (2)C3—C4—C5—N2177.8 (2)
C6—C1—C2—C30.8 (4)C7—C4—C5—N20.7 (4)
S1—C1—C2—C3176.4 (2)C4—C5—C6—C11.7 (4)
C1—C2—C3—N1174.1 (3)N2—C5—C6—C1179.6 (2)
C1—C2—C3—C42.7 (4)C2—C1—C6—C50.2 (4)
N1—C3—C4—C5172.8 (3)S1—C1—C6—C5176.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n1···O1i0.85 (1)2.13 (1)2.950 (3)164 (3)
N1—H1n2···O1ii0.85 (1)2.17 (2)2.936 (3)150 (2)
N2—H2n1···O2iii0.85 (1)2.25 (3)2.854 (3)128 (3)
N2—H2n2···O3iv0.86 (1)1.94 (1)2.788 (3)173 (3)
N2—H2n3···O2v0.86 (1)1.96 (1)2.806 (3)168 (3)
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y1/2, z+3/2; (iii) x, y, z1; (iv) x, y+3/2, z1/2; (v) x, y+1, z+1.
 

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