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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
CCDC reference: 255899
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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
C10H9NO3S | F(000) = 928 |
Mr = 223.24 | Dx = 1.558 Mg m−3 |
Orthorhombic, Pbca | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 25 reflections |
a = 11.120 (2) Å | θ = 15–20° |
b = 10.529 (2) Å | µ = 2.93 mm−1 |
c = 16.253 (3) Å | T = 295 K |
V = 1902.9 (6) Å3 | Block, violet |
Z = 8 | 0.30 × 0.20 × 0.20 mm |
Data collection top
Enraf–Nonius CAD-4f four-circle diffractometer | Rint = 0.033 |
Radiation source: Sealed tube | θmax = 68°, θmin = 5.4° |
Nickel filtered monochromator | h = −1→13 |
ω–2θ scans | k = −12→1 |
2124 measured reflections | l = −19→1 |
1725 independent reflections | 3 standard reflections every 160 min |
1496 reflections with I > 2σ(I) | intensity decay: 2.0% |
Refinement top
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)] = 0.039 | H 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 reflections | Δρmax = 0.42 e Å−3 |
149 parameters | Δρmin = −0.47 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
S2 | 0.35321 (5) | 0.18955 (5) | 0.65915 (3) | 0.0246 (2) | |
O21 | 0.41215 (16) | 0.26283 (16) | 0.72337 (9) | 0.0371 (5) | |
O22 | 0.41330 (18) | 0.06917 (16) | 0.64632 (10) | 0.0428 (6) | |
O23 | 0.22588 (16) | 0.1796 (2) | 0.67311 (12) | 0.0494 (7) | |
N5 | 0.52637 (18) | 0.48460 (19) | 0.29788 (12) | 0.0284 (6) | |
C1 | 0.28630 (19) | 0.3614 (2) | 0.54248 (14) | 0.0268 (6) | |
C2 | 0.37230 (19) | 0.2778 (2) | 0.56725 (13) | 0.0245 (6) | |
C3 | 0.4794 (2) | 0.2627 (2) | 0.52104 (13) | 0.0284 (7) | |
C4 | 0.4963 (2) | 0.3309 (2) | 0.45091 (14) | 0.0276 (6) | |
C5 | 0.4196 (2) | 0.4931 (2) | 0.35065 (13) | 0.0262 (6) | |
C6 | 0.3332 (2) | 0.5769 (2) | 0.32715 (14) | 0.0327 (7) | |
C7 | 0.2281 (2) | 0.5910 (2) | 0.37435 (15) | 0.0356 (8) | |
C8 | 0.2124 (2) | 0.5204 (2) | 0.44400 (15) | 0.0328 (7) | |
C9 | 0.30121 (19) | 0.43372 (19) | 0.46963 (13) | 0.0249 (6) | |
C10 | 0.40878 (19) | 0.41789 (19) | 0.42263 (13) | 0.0236 (6) | |
H1 | 0.216900 | 0.371200 | 0.573700 | 0.0320* | |
H3 | 0.538200 | 0.206100 | 0.538700 | 0.0340* | |
H4 | 0.566800 | 0.320000 | 0.421000 | 0.0330* | |
H5A | 0.585 (3) | 0.433 (3) | 0.3164 (19) | 0.045 (8)* | |
H5B | 0.567 (3) | 0.569 (3) | 0.291 (2) | 0.061 (9)* | |
H5C | 0.503 (3) | 0.454 (4) | 0.242 (3) | 0.079 (11)* | |
H6 | 0.343600 | 0.625000 | 0.279700 | 0.0390* | |
H7 | 0.169200 | 0.648500 | 0.358100 | 0.0430* | |
H8 | 0.142400 | 0.529700 | 0.474800 | 0.0390* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S2 | 0.0277 (4) | 0.0221 (3) | 0.0241 (3) | −0.0028 (2) | −0.0019 (2) | 0.0045 (2) |
O21 | 0.0539 (11) | 0.0312 (9) | 0.0263 (8) | −0.0111 (8) | −0.0037 (7) | 0.0010 (7) |
O22 | 0.0707 (13) | 0.0262 (9) | 0.0316 (9) | 0.0123 (9) | −0.0001 (8) | 0.0050 (7) |
O23 | 0.0305 (10) | 0.0696 (14) | 0.0480 (11) | −0.0129 (9) | −0.0051 (8) | 0.0289 (10) |
N5 | 0.0333 (11) | 0.0254 (10) | 0.0265 (10) | −0.0042 (9) | −0.0016 (8) | 0.0006 (8) |
C1 | 0.0272 (11) | 0.0254 (11) | 0.0278 (11) | 0.0005 (9) | 0.0025 (9) | −0.0013 (9) |
C2 | 0.0305 (11) | 0.0196 (10) | 0.0233 (11) | −0.0030 (9) | −0.0017 (9) | 0.0010 (9) |
C3 | 0.0283 (12) | 0.0253 (11) | 0.0316 (12) | 0.0043 (9) | −0.0025 (9) | 0.0038 (9) |
C4 | 0.0267 (11) | 0.0275 (11) | 0.0287 (11) | 0.0016 (9) | 0.0025 (9) | 0.0009 (9) |
C5 | 0.0337 (12) | 0.0222 (11) | 0.0228 (10) | −0.0051 (9) | −0.0021 (9) | −0.0022 (8) |
C6 | 0.0452 (14) | 0.0261 (12) | 0.0269 (12) | 0.0016 (10) | −0.0046 (10) | 0.0046 (9) |
C7 | 0.0423 (14) | 0.0293 (12) | 0.0353 (13) | 0.0112 (10) | −0.0038 (10) | 0.0043 (10) |
C8 | 0.0348 (12) | 0.0295 (12) | 0.0341 (12) | 0.0077 (10) | 0.0008 (10) | 0.0002 (10) |
C9 | 0.0302 (11) | 0.0190 (10) | 0.0254 (11) | 0.0006 (9) | −0.0010 (9) | −0.0024 (8) |
C10 | 0.0293 (11) | 0.0174 (10) | 0.0242 (10) | −0.0027 (8) | −0.0023 (9) | −0.0027 (8) |
Geometric parameters (Å, º) top
S2—O21 | 1.4541 (17) | C5—C10 | 1.418 (3) |
S2—O22 | 1.4479 (19) | C5—C6 | 1.359 (3) |
S2—O23 | 1.4378 (19) | C6—C7 | 1.406 (3) |
S2—C2 | 1.772 (2) | C7—C8 | 1.365 (3) |
N5—C5 | 1.467 (3) | C8—C9 | 1.408 (3) |
N5—H5C | 1.00 (5) | C9—C10 | 1.429 (3) |
N5—H5A | 0.90 (3) | C1—H1 | 0.9293 |
N5—H5B | 1.00 (3) | C3—H3 | 0.9301 |
C1—C2 | 1.361 (3) | C4—H4 | 0.9296 |
C1—C9 | 1.417 (3) | C6—H6 | 0.9298 |
C2—C3 | 1.417 (3) | C7—H7 | 0.9302 |
C3—C4 | 1.360 (3) | C8—H8 | 0.9306 |
C4—C10 | 1.413 (3) | | |
| | | |
O21—S2—O22 | 111.09 (10) | C5—C6—C7 | 120.2 (2) |
O21—S2—O23 | 111.67 (11) | C6—C7—C8 | 120.1 (2) |
O21—S2—C2 | 105.83 (10) | C7—C8—C9 | 120.6 (2) |
O22—S2—O23 | 114.42 (12) | C1—C9—C10 | 118.80 (19) |
O22—S2—C2 | 106.40 (10) | C1—C9—C8 | 120.9 (2) |
O23—S2—C2 | 106.81 (11) | C8—C9—C10 | 120.31 (19) |
H5A—N5—H5C | 107 (3) | C5—C10—C9 | 116.55 (19) |
H5B—N5—H5C | 108 (3) | C4—C10—C5 | 124.9 (2) |
C5—N5—H5C | 110 (2) | C4—C10—C9 | 118.57 (19) |
C5—N5—H5A | 115 (2) | C2—C1—H1 | 119.60 |
C5—N5—H5B | 112.1 (19) | C9—C1—H1 | 119.57 |
H5A—N5—H5B | 104 (3) | C2—C3—H3 | 119.95 |
C2—C1—C9 | 120.8 (2) | C4—C3—H3 | 119.98 |
S2—C2—C3 | 119.25 (16) | C3—C4—H4 | 119.31 |
S2—C2—C1 | 120.30 (17) | C10—C4—H4 | 119.39 |
C1—C2—C3 | 120.4 (2) | C5—C6—H6 | 119.91 |
C2—C3—C4 | 120.1 (2) | C7—C6—H6 | 119.90 |
C3—C4—C10 | 121.3 (2) | C6—C7—H7 | 119.94 |
C6—C5—C10 | 122.3 (2) | C8—C7—H7 | 119.98 |
N5—C5—C6 | 116.57 (19) | C7—C8—H8 | 119.71 |
N5—C5—C10 | 121.12 (19) | C9—C8—H8 | 119.72 |
| | | |
O21—S2—C2—C3 | 85.07 (19) | N5—C5—C10—C4 | 0.6 (3) |
O22—S2—C2—C3 | −33.2 (2) | C10—C5—C6—C7 | −0.4 (3) |
O23—S2—C2—C3 | −155.81 (18) | N5—C5—C6—C7 | −179.9 (2) |
O23—S2—C2—C1 | 25.8 (2) | C6—C5—C10—C9 | 0.4 (3) |
O21—S2—C2—C1 | −93.33 (19) | N5—C5—C10—C9 | 179.9 (3) |
O22—S2—C2—C1 | 148.41 (18) | C6—C5—C10—C4 | −178.9 (2) |
C9—C1—C2—C3 | 0.8 (3) | C5—C6—C7—C8 | −0.1 (3) |
C2—C1—C9—C10 | −0.3 (3) | C6—C7—C8—C9 | 0.5 (3) |
C9—C1—C2—S2 | 179.20 (15) | C7—C8—C9—C10 | −0.4 (3) |
C2—C1—C9—C8 | −179.9 (2) | C7—C8—C9—C1 | 179.1 (2) |
S2—C2—C3—C4 | −179.14 (17) | C1—C9—C10—C5 | −179.56 (19) |
C1—C2—C3—C4 | −0.7 (3) | C8—C9—C10—C4 | 179.3 (2) |
C2—C3—C4—C10 | 0.2 (3) | C1—C9—C10—C4 | −0.2 (3) |
C3—C4—C10—C5 | 179.6 (2) | C8—C9—C10—C5 | 0.0 (3) |
C3—C4—C10—C9 | 0.3 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5A···O23i | 0.90 (3) | 1.97 (3) | 2.852 (3) | 165 (3) |
N5—H5B···O21ii | 1.00 (3) | 1.80 (3) | 2.767 (3) | 161 (3) |
N5—H5C···O21iii | 1.00 (5) | 2.51 (4) | 3.141 (3) | 120 (3) |
N5—H5C···O22iii | 1.00 (5) | 1.86 (4) | 2.823 (3) | 160 (3) |
C1—H1···O23 | 0.93 | 2.59 | 2.937 (3) | 103 |
C4—H4···O23i | 0.93 | 2.34 | 3.255 (3) | 168 |
C7—H7···O21iv | 0.93 | 2.55 | 3.290 (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, z−1/2; (iv) −x+1/2, −y+1, z−1/2. |
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