The crystal structure of anhydrous sodium 2-aminobenzenesulfonate, [Na(C6H6NO3S)]n, reveals the presence of a two-dimensional sandwich polymer structure based on a distorted octahedral six-coordinate NaO5N repeating unit. O-Donor atoms are from five different sulfonate groups [Na-O = 2.294 (3)-2.532 (3) Å] and an amine nitrogen [Na-N = 2.572 (3) Å], completing a six-membered chelate ring including Na. Hydrogen bonds also stabilize the core structure. The outer layers of the sandwich comprise the unassociated benzene rings.
Supporting information
CCDC reference: 242059
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.040
- wR factor = 0.153
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.88 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
1 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: MSC/AFC Diffractometer Control Software (Molecular Structure
Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON for Windows (Spek, 1999); software used to prepare material for publication: PLATON for Windows.
Crystal data top
[Na(C6H6NO3S)] | F(000) = 400 |
Mr = 195.17 | Dx = 1.631 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 14.213 (4) Å | θ = 12.7–17.2° |
b = 4.9447 (12) Å | µ = 0.42 mm−1 |
c = 11.401 (2) Å | T = 298 K |
β = 97.284 (19)° | Plate, colourless |
V = 794.8 (3) Å3 | 0.45 × 0.30 × 0.10 mm |
Z = 4 | |
Data collection top
Rigaku AFC-7R diffractometer | 1432 reflections with I > 2σ(I) |
Radiation source: Rigaku rotating anode | Rint = 0.029 |
Graphite monochromator | θmax = 27.5°, θmin = 2.9° |
ω–2θ scans | h = −7→18 |
Absorption correction: ψ scan (TEXSAN for Windows; Molecular Structure Corporation, 1999) | k = −6→2 |
Tmin = 0.859, Tmax = 0.959 | l = −14→14 |
2137 measured reflections | 3 standard reflections every 150 reflections |
1834 independent reflections | intensity decay: 5.9% |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.153 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.89 | w = 1/[σ2(Fo2) + (0.1P)2 + 1.9146P] where P = (Fo2 + 2Fc2)/3 |
1834 reflections | (Δ/σ)max = 0.011 |
118 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.58 e Å−3 |
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 | |
S1 | 0.37746 (5) | −0.02872 (13) | 0.06610 (5) | 0.0214 (2) | |
Na1 | 0.55349 (9) | 0.5169 (2) | 0.13394 (10) | 0.0279 (4) | |
O1 | 0.36861 (19) | −0.1895 (4) | −0.04111 (18) | 0.0348 (7) | |
O2 | 0.40962 (16) | 0.2463 (4) | 0.04878 (19) | 0.0302 (7) | |
O3 | 0.43445 (15) | −0.1611 (4) | 0.16569 (17) | 0.0267 (6) | |
N2 | 0.3163 (2) | 0.3212 (6) | 0.2585 (2) | 0.0334 (8) | |
C1 | 0.2619 (2) | −0.0071 (6) | 0.1071 (3) | 0.0260 (8) | |
C2 | 0.2440 (2) | 0.1617 (7) | 0.2011 (3) | 0.0305 (9) | |
C3 | 0.1555 (3) | 0.1521 (9) | 0.2392 (4) | 0.0546 (14) | |
C4 | 0.0860 (3) | −0.0134 (12) | 0.1841 (6) | 0.075 (2) | |
C5 | 0.1013 (3) | −0.1747 (11) | 0.0893 (6) | 0.0716 (18) | |
C6 | 0.1902 (3) | −0.1730 (8) | 0.0518 (4) | 0.0460 (11) | |
H2A | 0.362 (3) | 0.395 (9) | 0.215 (4) | 0.044 (11)* | |
H2B | 0.295 (3) | 0.435 (10) | 0.305 (4) | 0.056 (14)* | |
H3 | 0.1431 | 0.2643 | 0.3049 | 0.0650* | |
H4 | 0.0249 | −0.0183 | 0.2125 | 0.0840* | |
H5 | 0.0518 | −0.2876 | 0.0502 | 0.0840* | |
H6 | 0.2025 | −0.2861 | −0.0141 | 0.0530* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0354 (4) | 0.0157 (3) | 0.0137 (3) | 0.0026 (3) | 0.0059 (2) | 0.0005 (2) |
Na1 | 0.0403 (7) | 0.0260 (6) | 0.0175 (6) | 0.0049 (5) | 0.0042 (5) | −0.0028 (4) |
O1 | 0.0659 (16) | 0.0235 (11) | 0.0157 (10) | 0.0066 (10) | 0.0076 (9) | −0.0041 (8) |
O2 | 0.0451 (13) | 0.0203 (11) | 0.0271 (10) | −0.0025 (9) | 0.0119 (9) | 0.0010 (8) |
O3 | 0.0368 (11) | 0.0259 (11) | 0.0178 (9) | 0.0064 (9) | 0.0050 (8) | 0.0030 (8) |
N2 | 0.0433 (16) | 0.0333 (15) | 0.0247 (13) | 0.0016 (13) | 0.0087 (11) | −0.0097 (12) |
C1 | 0.0267 (14) | 0.0255 (14) | 0.0252 (14) | 0.0020 (11) | 0.0013 (11) | 0.0012 (11) |
C2 | 0.0347 (15) | 0.0293 (16) | 0.0284 (15) | 0.0049 (13) | 0.0073 (12) | 0.0008 (12) |
C3 | 0.048 (2) | 0.052 (2) | 0.069 (3) | 0.006 (2) | 0.028 (2) | −0.003 (2) |
C4 | 0.0264 (19) | 0.080 (4) | 0.122 (5) | −0.004 (2) | 0.022 (2) | −0.009 (3) |
C5 | 0.0308 (19) | 0.064 (3) | 0.116 (4) | −0.017 (2) | −0.006 (2) | −0.012 (3) |
C6 | 0.0414 (19) | 0.040 (2) | 0.053 (2) | −0.0048 (16) | −0.0078 (16) | −0.0073 (17) |
Geometric parameters (Å, º) top
S1—O1 | 1.450 (2) | N2—H2A | 0.94 (4) |
S1—O2 | 1.456 (2) | C1—C6 | 1.395 (5) |
S1—O3 | 1.463 (2) | C1—C2 | 1.407 (5) |
S1—C1 | 1.767 (3) | C2—C3 | 1.383 (5) |
Na1—O2 | 2.532 (3) | C3—C4 | 1.372 (7) |
Na1—O3i | 2.384 (2) | C4—C5 | 1.382 (9) |
Na1—O3ii | 2.434 (2) | C5—C6 | 1.384 (6) |
Na1—N2ii | 2.572 (3) | C3—H3 | 0.9661 |
Na1—O1iii | 2.294 (3) | C4—H4 | 0.9648 |
Na1—O2iv | 2.503 (3) | C5—H5 | 0.9622 |
N2—C2 | 1.391 (4) | C6—H6 | 0.9701 |
N2—H2B | 0.85 (5) | | |
| | | |
O1—S1—O2 | 113.13 (13) | S1—O3—Na1vi | 122.20 (12) |
O1—S1—O3 | 112.90 (13) | Na1v—O3—Na1vi | 114.65 (9) |
O1—S1—C1 | 105.78 (16) | Na1vi—N2—C2 | 109.7 (2) |
O2—S1—O3 | 111.76 (13) | Na1vi—N2—H2B | 112 (3) |
O2—S1—C1 | 107.32 (14) | C2—N2—H2B | 112 (3) |
O3—S1—C1 | 105.28 (14) | H2A—N2—H2B | 113 (4) |
O2—Na1—O3i | 81.78 (8) | C2—N2—H2A | 119 (3) |
O2—Na1—O3ii | 97.25 (8) | Na1vi—N2—H2A | 89 (3) |
O2—Na1—N2ii | 171.54 (10) | S1—C1—C6 | 119.7 (3) |
O1iii—Na1—O2 | 82.17 (9) | C2—C1—C6 | 120.1 (3) |
O2—Na1—O2iv | 99.92 (8) | S1—C1—C2 | 120.1 (2) |
O3i—Na1—O3ii | 93.78 (8) | N2—C2—C3 | 121.3 (3) |
O3i—Na1—N2ii | 91.06 (9) | C1—C2—C3 | 118.6 (3) |
O1iii—Na1—O3i | 159.15 (10) | N2—C2—C1 | 120.0 (3) |
O2iv—Na1—O3i | 92.38 (8) | C2—C3—C4 | 120.5 (4) |
O3ii—Na1—N2ii | 78.66 (8) | C3—C4—C5 | 121.8 (4) |
O1iii—Na1—O3ii | 101.37 (8) | C4—C5—C6 | 118.6 (5) |
O2iv—Na1—O3ii | 162.42 (9) | C1—C6—C5 | 120.5 (4) |
O1iii—Na1—N2ii | 105.82 (10) | C2—C3—H3 | 119.11 |
O2iv—Na1—N2ii | 84.79 (8) | C4—C3—H3 | 120.39 |
O1iii—Na1—O2iv | 77.40 (8) | C3—C4—H4 | 119.19 |
S1—O1—Na1iii | 141.29 (16) | C5—C4—H4 | 119.04 |
S1—O2—Na1 | 133.92 (13) | C4—C5—H5 | 121.24 |
S1—O2—Na1iv | 130.72 (13) | C6—C5—H5 | 120.19 |
Na1—O2—Na1iv | 80.08 (8) | C1—C6—H6 | 119.73 |
S1—O3—Na1v | 120.98 (12) | C5—C6—H6 | 119.79 |
| | | |
O2—S1—O1—Na1iii | 101.2 (2) | O1iii—Na1—O2—S1 | 63.02 (18) |
O3—S1—O1—Na1iii | −27.0 (3) | O1iii—Na1—O2—Na1iv | −75.66 (8) |
C1—S1—O1—Na1iii | −141.6 (2) | O2iv—Na1—O2—S1 | 138.68 (17) |
O1—S1—O2—Na1 | −118.88 (19) | O2iv—Na1—O2—Na1iv | 0.00 (8) |
O1—S1—O2—Na1iv | 2.0 (2) | O2—Na1—O3i—S1i | −67.24 (14) |
O3—S1—O2—Na1 | 9.9 (2) | O2—Na1—O3i—Na1ii | 129.16 (10) |
O3—S1—O2—Na1iv | 130.78 (16) | O2—Na1—O3ii—Na1vi | −0.77 (11) |
C1—S1—O2—Na1 | 124.82 (19) | O2—Na1—O3ii—S1ii | −164.14 (14) |
C1—S1—O2—Na1iv | −114.29 (18) | O2—Na1—O1iii—S1iii | 38.3 (2) |
O1—S1—O3—Na1v | 26.47 (19) | O2—Na1—O2iv—S1iv | 141.14 (17) |
O1—S1—O3—Na1vi | −171.19 (14) | O2—Na1—O2iv—Na1iv | 0.00 (8) |
O2—S1—O3—Na1v | −102.42 (15) | Na1vi—N2—C2—C1 | −65.3 (3) |
O2—S1—O3—Na1vi | 59.92 (17) | Na1vi—N2—C2—C3 | 110.6 (3) |
C1—S1—O3—Na1v | 141.39 (14) | S1—C1—C2—C3 | −173.1 (3) |
C1—S1—O3—Na1vi | −56.26 (17) | C6—C1—C2—N2 | 178.1 (3) |
O1—S1—C1—C2 | −172.9 (3) | C6—C1—C2—C3 | 2.1 (5) |
O1—S1—C1—C6 | 11.8 (3) | S1—C1—C2—N2 | 2.9 (4) |
O2—S1—C1—C2 | −51.9 (3) | S1—C1—C6—C5 | 174.7 (4) |
O2—S1—C1—C6 | 132.9 (3) | C2—C1—C6—C5 | −0.5 (6) |
O3—S1—C1—C2 | 67.3 (3) | N2—C2—C3—C4 | −177.7 (4) |
O3—S1—C1—C6 | −107.9 (3) | C1—C2—C3—C4 | −1.8 (6) |
O3i—Na1—O2—S1 | −130.33 (18) | C2—C3—C4—C5 | −0.2 (8) |
O3i—Na1—O2—Na1iv | 90.99 (7) | C3—C4—C5—C6 | 1.8 (9) |
O3ii—Na1—O2—S1 | −37.53 (19) | C4—C5—C6—C1 | −1.4 (8) |
O3ii—Na1—O2—Na1iv | −176.21 (8) | | |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, −y, −z; (iv) −x+1, −y+1, −z; (v) x, y−1, z; (vi) −x+1, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2 | 0.94 (4) | 2.22 (4) | 2.901 (3) | 129 (4) |
N2—H2A···O3i | 0.94 (4) | 2.52 (4) | 3.308 (4) | 142 (4) |
N2—H2B···O1vii | 0.85 (5) | 2.30 (5) | 2.942 (3) | 132 (4) |
C6—H6···O1 | 0.97 | 2.47 | 2.871 (5) | 105 |
Symmetry codes: (i) x, y+1, z; (vii) x, −y+1/2, z+1/2. |