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The crystal structure of 5-amino-2-naphthalene­sulfonic acid (1,6-Cleve's acid), C10H9NO3S, shows the presence of a sulfonate-aminium group zwitterion, viz. 5-ammonio-2-naphthalene­sulfonate. All aminium H atoms are involved in head-to-tail intermolecular hydrogen-bonding interactions with separate sulfonate O-atom acceptors, giving a three-dimensional framework polymer structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804025206/bt6536sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804025206/bt6536Isup2.hkl
Contains datablock I

CCDC reference: 255899

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.105
  • Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: WinGX (Farrugia, 1999); program(s) used to refine structure: WinGX; molecular graphics: PLATON for Windows (Spek, 1999); software used to prepare material for publication: PLATON for Windows.

5-ammonio-2-naphthalenesulfonate top
Crystal data top
C10H9NO3SF(000) = 928
Mr = 223.24Dx = 1.558 Mg m3
Orthorhombic, PbcaCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 11.120 (2) Åθ = 15–20°
b = 10.529 (2) ŵ = 2.93 mm1
c = 16.253 (3) ÅT = 295 K
V = 1902.9 (6) Å3Block, violet
Z = 80.30 × 0.20 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4f four-circle
diffractometer
Rint = 0.033
Radiation source: Sealed tubeθmax = 68°, θmin = 5.4°
Nickel filtered monochromatorh = 113
ω–2θ scansk = 121
2124 measured reflectionsl = 191
1725 independent reflections3 standard reflections every 160 min
1496 reflections with I > 2σ(I) intensity decay: 2.0%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.0553P)2 + 1.9163P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
1605 reflectionsΔρmax = 0.42 e Å3
149 parametersΔρmin = 0.47 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0030 (4)
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S20.35321 (5)0.18955 (5)0.65915 (3)0.0246 (2)
O210.41215 (16)0.26283 (16)0.72337 (9)0.0371 (5)
O220.41330 (18)0.06917 (16)0.64632 (10)0.0428 (6)
O230.22588 (16)0.1796 (2)0.67311 (12)0.0494 (7)
N50.52637 (18)0.48460 (19)0.29788 (12)0.0284 (6)
C10.28630 (19)0.3614 (2)0.54248 (14)0.0268 (6)
C20.37230 (19)0.2778 (2)0.56725 (13)0.0245 (6)
C30.4794 (2)0.2627 (2)0.52104 (13)0.0284 (7)
C40.4963 (2)0.3309 (2)0.45091 (14)0.0276 (6)
C50.4196 (2)0.4931 (2)0.35065 (13)0.0262 (6)
C60.3332 (2)0.5769 (2)0.32715 (14)0.0327 (7)
C70.2281 (2)0.5910 (2)0.37435 (15)0.0356 (8)
C80.2124 (2)0.5204 (2)0.44400 (15)0.0328 (7)
C90.30121 (19)0.43372 (19)0.46963 (13)0.0249 (6)
C100.40878 (19)0.41789 (19)0.42263 (13)0.0236 (6)
H10.2169000.3712000.5737000.0320*
H30.5382000.2061000.5387000.0340*
H40.5668000.3200000.4210000.0330*
H5A0.585 (3)0.433 (3)0.3164 (19)0.045 (8)*
H5B0.567 (3)0.569 (3)0.291 (2)0.061 (9)*
H5C0.503 (3)0.454 (4)0.242 (3)0.079 (11)*
H60.3436000.6250000.2797000.0390*
H70.1692000.6485000.3581000.0430*
H80.1424000.5297000.4748000.0390*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S20.0277 (4)0.0221 (3)0.0241 (3)0.0028 (2)0.0019 (2)0.0045 (2)
O210.0539 (11)0.0312 (9)0.0263 (8)0.0111 (8)0.0037 (7)0.0010 (7)
O220.0707 (13)0.0262 (9)0.0316 (9)0.0123 (9)0.0001 (8)0.0050 (7)
O230.0305 (10)0.0696 (14)0.0480 (11)0.0129 (9)0.0051 (8)0.0289 (10)
N50.0333 (11)0.0254 (10)0.0265 (10)0.0042 (9)0.0016 (8)0.0006 (8)
C10.0272 (11)0.0254 (11)0.0278 (11)0.0005 (9)0.0025 (9)0.0013 (9)
C20.0305 (11)0.0196 (10)0.0233 (11)0.0030 (9)0.0017 (9)0.0010 (9)
C30.0283 (12)0.0253 (11)0.0316 (12)0.0043 (9)0.0025 (9)0.0038 (9)
C40.0267 (11)0.0275 (11)0.0287 (11)0.0016 (9)0.0025 (9)0.0009 (9)
C50.0337 (12)0.0222 (11)0.0228 (10)0.0051 (9)0.0021 (9)0.0022 (8)
C60.0452 (14)0.0261 (12)0.0269 (12)0.0016 (10)0.0046 (10)0.0046 (9)
C70.0423 (14)0.0293 (12)0.0353 (13)0.0112 (10)0.0038 (10)0.0043 (10)
C80.0348 (12)0.0295 (12)0.0341 (12)0.0077 (10)0.0008 (10)0.0002 (10)
C90.0302 (11)0.0190 (10)0.0254 (11)0.0006 (9)0.0010 (9)0.0024 (8)
C100.0293 (11)0.0174 (10)0.0242 (10)0.0027 (8)0.0023 (9)0.0027 (8)
Geometric parameters (Å, º) top
S2—O211.4541 (17)C5—C101.418 (3)
S2—O221.4479 (19)C5—C61.359 (3)
S2—O231.4378 (19)C6—C71.406 (3)
S2—C21.772 (2)C7—C81.365 (3)
N5—C51.467 (3)C8—C91.408 (3)
N5—H5C1.00 (5)C9—C101.429 (3)
N5—H5A0.90 (3)C1—H10.9293
N5—H5B1.00 (3)C3—H30.9301
C1—C21.361 (3)C4—H40.9296
C1—C91.417 (3)C6—H60.9298
C2—C31.417 (3)C7—H70.9302
C3—C41.360 (3)C8—H80.9306
C4—C101.413 (3)
O21—S2—O22111.09 (10)C5—C6—C7120.2 (2)
O21—S2—O23111.67 (11)C6—C7—C8120.1 (2)
O21—S2—C2105.83 (10)C7—C8—C9120.6 (2)
O22—S2—O23114.42 (12)C1—C9—C10118.80 (19)
O22—S2—C2106.40 (10)C1—C9—C8120.9 (2)
O23—S2—C2106.81 (11)C8—C9—C10120.31 (19)
H5A—N5—H5C107 (3)C5—C10—C9116.55 (19)
H5B—N5—H5C108 (3)C4—C10—C5124.9 (2)
C5—N5—H5C110 (2)C4—C10—C9118.57 (19)
C5—N5—H5A115 (2)C2—C1—H1119.60
C5—N5—H5B112.1 (19)C9—C1—H1119.57
H5A—N5—H5B104 (3)C2—C3—H3119.95
C2—C1—C9120.8 (2)C4—C3—H3119.98
S2—C2—C3119.25 (16)C3—C4—H4119.31
S2—C2—C1120.30 (17)C10—C4—H4119.39
C1—C2—C3120.4 (2)C5—C6—H6119.91
C2—C3—C4120.1 (2)C7—C6—H6119.90
C3—C4—C10121.3 (2)C6—C7—H7119.94
C6—C5—C10122.3 (2)C8—C7—H7119.98
N5—C5—C6116.57 (19)C7—C8—H8119.71
N5—C5—C10121.12 (19)C9—C8—H8119.72
O21—S2—C2—C385.07 (19)N5—C5—C10—C40.6 (3)
O22—S2—C2—C333.2 (2)C10—C5—C6—C70.4 (3)
O23—S2—C2—C3155.81 (18)N5—C5—C6—C7179.9 (2)
O23—S2—C2—C125.8 (2)C6—C5—C10—C90.4 (3)
O21—S2—C2—C193.33 (19)N5—C5—C10—C9179.9 (3)
O22—S2—C2—C1148.41 (18)C6—C5—C10—C4178.9 (2)
C9—C1—C2—C30.8 (3)C5—C6—C7—C80.1 (3)
C2—C1—C9—C100.3 (3)C6—C7—C8—C90.5 (3)
C9—C1—C2—S2179.20 (15)C7—C8—C9—C100.4 (3)
C2—C1—C9—C8179.9 (2)C7—C8—C9—C1179.1 (2)
S2—C2—C3—C4179.14 (17)C1—C9—C10—C5179.56 (19)
C1—C2—C3—C40.7 (3)C8—C9—C10—C4179.3 (2)
C2—C3—C4—C100.2 (3)C1—C9—C10—C40.2 (3)
C3—C4—C10—C5179.6 (2)C8—C9—C10—C50.0 (3)
C3—C4—C10—C90.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···O23i0.90 (3)1.97 (3)2.852 (3)165 (3)
N5—H5B···O21ii1.00 (3)1.80 (3)2.767 (3)161 (3)
N5—H5C···O21iii1.00 (5)2.51 (4)3.141 (3)120 (3)
N5—H5C···O22iii1.00 (5)1.86 (4)2.823 (3)160 (3)
C1—H1···O230.932.592.937 (3)103
C4—H4···O23i0.932.343.255 (3)168
C7—H7···O21iv0.932.553.290 (3)137
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x+1, y+1, z+1; (iii) x, y+1/2, z1/2; (iv) x+1/2, y+1, z1/2.
 

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