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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804011456/hb6040sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804011456/hb6040Isup2.hkl
Contains datablock I

CCDC reference: 242059

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Computing details top

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.

(I) top
Crystal data top
[Na(C6H6NO3S)]F(000) = 400
Mr = 195.17Dx = 1.631 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 14.213 (4) Åθ = 12.7–17.2°
b = 4.9447 (12) ŵ = 0.42 mm1
c = 11.401 (2) ÅT = 298 K
β = 97.284 (19)°Plate, colourless
V = 794.8 (3) Å30.45 × 0.30 × 0.10 mm
Z = 4
Data collection top
Rigaku AFC-7R
diffractometer
1432 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anodeRint = 0.029
Graphite monochromatorθmax = 27.5°, θmin = 2.9°
ω–2θ scansh = 718
Absorption correction: ψ scan
(TEXSAN for Windows; Molecular Structure Corporation, 1999)
k = 62
Tmin = 0.859, Tmax = 0.959l = 1414
2137 measured reflections3 standard reflections every 150 reflections
1834 independent reflections intensity decay: 5.9%
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H 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 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.58 e Å3
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
S10.37746 (5)0.02872 (13)0.06610 (5)0.0214 (2)
Na10.55349 (9)0.5169 (2)0.13394 (10)0.0279 (4)
O10.36861 (19)0.1895 (4)0.04111 (18)0.0348 (7)
O20.40962 (16)0.2463 (4)0.04878 (19)0.0302 (7)
O30.43445 (15)0.1611 (4)0.16569 (17)0.0267 (6)
N20.3163 (2)0.3212 (6)0.2585 (2)0.0334 (8)
C10.2619 (2)0.0071 (6)0.1071 (3)0.0260 (8)
C20.2440 (2)0.1617 (7)0.2011 (3)0.0305 (9)
C30.1555 (3)0.1521 (9)0.2392 (4)0.0546 (14)
C40.0860 (3)0.0134 (12)0.1841 (6)0.075 (2)
C50.1013 (3)0.1747 (11)0.0893 (6)0.0716 (18)
C60.1902 (3)0.1730 (8)0.0518 (4)0.0460 (11)
H2A0.362 (3)0.395 (9)0.215 (4)0.044 (11)*
H2B0.295 (3)0.435 (10)0.305 (4)0.056 (14)*
H30.14310.26430.30490.0650*
H40.02490.01830.21250.0840*
H50.05180.28760.05020.0840*
H60.20250.28610.01410.0530*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0354 (4)0.0157 (3)0.0137 (3)0.0026 (3)0.0059 (2)0.0005 (2)
Na10.0403 (7)0.0260 (6)0.0175 (6)0.0049 (5)0.0042 (5)0.0028 (4)
O10.0659 (16)0.0235 (11)0.0157 (10)0.0066 (10)0.0076 (9)0.0041 (8)
O20.0451 (13)0.0203 (11)0.0271 (10)0.0025 (9)0.0119 (9)0.0010 (8)
O30.0368 (11)0.0259 (11)0.0178 (9)0.0064 (9)0.0050 (8)0.0030 (8)
N20.0433 (16)0.0333 (15)0.0247 (13)0.0016 (13)0.0087 (11)0.0097 (12)
C10.0267 (14)0.0255 (14)0.0252 (14)0.0020 (11)0.0013 (11)0.0012 (11)
C20.0347 (15)0.0293 (16)0.0284 (15)0.0049 (13)0.0073 (12)0.0008 (12)
C30.048 (2)0.052 (2)0.069 (3)0.006 (2)0.028 (2)0.003 (2)
C40.0264 (19)0.080 (4)0.122 (5)0.004 (2)0.022 (2)0.009 (3)
C50.0308 (19)0.064 (3)0.116 (4)0.017 (2)0.006 (2)0.012 (3)
C60.0414 (19)0.040 (2)0.053 (2)0.0048 (16)0.0078 (16)0.0073 (17)
Geometric parameters (Å, º) top
S1—O11.450 (2)N2—H2A0.94 (4)
S1—O21.456 (2)C1—C61.395 (5)
S1—O31.463 (2)C1—C21.407 (5)
S1—C11.767 (3)C2—C31.383 (5)
Na1—O22.532 (3)C3—C41.372 (7)
Na1—O3i2.384 (2)C4—C51.382 (9)
Na1—O3ii2.434 (2)C5—C61.384 (6)
Na1—N2ii2.572 (3)C3—H30.9661
Na1—O1iii2.294 (3)C4—H40.9648
Na1—O2iv2.503 (3)C5—H50.9622
N2—C21.391 (4)C6—H60.9701
N2—H2B0.85 (5)
O1—S1—O2113.13 (13)S1—O3—Na1vi122.20 (12)
O1—S1—O3112.90 (13)Na1v—O3—Na1vi114.65 (9)
O1—S1—C1105.78 (16)Na1vi—N2—C2109.7 (2)
O2—S1—O3111.76 (13)Na1vi—N2—H2B112 (3)
O2—S1—C1107.32 (14)C2—N2—H2B112 (3)
O3—S1—C1105.28 (14)H2A—N2—H2B113 (4)
O2—Na1—O3i81.78 (8)C2—N2—H2A119 (3)
O2—Na1—O3ii97.25 (8)Na1vi—N2—H2A89 (3)
O2—Na1—N2ii171.54 (10)S1—C1—C6119.7 (3)
O1iii—Na1—O282.17 (9)C2—C1—C6120.1 (3)
O2—Na1—O2iv99.92 (8)S1—C1—C2120.1 (2)
O3i—Na1—O3ii93.78 (8)N2—C2—C3121.3 (3)
O3i—Na1—N2ii91.06 (9)C1—C2—C3118.6 (3)
O1iii—Na1—O3i159.15 (10)N2—C2—C1120.0 (3)
O2iv—Na1—O3i92.38 (8)C2—C3—C4120.5 (4)
O3ii—Na1—N2ii78.66 (8)C3—C4—C5121.8 (4)
O1iii—Na1—O3ii101.37 (8)C4—C5—C6118.6 (5)
O2iv—Na1—O3ii162.42 (9)C1—C6—C5120.5 (4)
O1iii—Na1—N2ii105.82 (10)C2—C3—H3119.11
O2iv—Na1—N2ii84.79 (8)C4—C3—H3120.39
O1iii—Na1—O2iv77.40 (8)C3—C4—H4119.19
S1—O1—Na1iii141.29 (16)C5—C4—H4119.04
S1—O2—Na1133.92 (13)C4—C5—H5121.24
S1—O2—Na1iv130.72 (13)C6—C5—H5120.19
Na1—O2—Na1iv80.08 (8)C1—C6—H6119.73
S1—O3—Na1v120.98 (12)C5—C6—H6119.79
O2—S1—O1—Na1iii101.2 (2)O1iii—Na1—O2—S163.02 (18)
O3—S1—O1—Na1iii27.0 (3)O1iii—Na1—O2—Na1iv75.66 (8)
C1—S1—O1—Na1iii141.6 (2)O2iv—Na1—O2—S1138.68 (17)
O1—S1—O2—Na1118.88 (19)O2iv—Na1—O2—Na1iv0.00 (8)
O1—S1—O2—Na1iv2.0 (2)O2—Na1—O3i—S1i67.24 (14)
O3—S1—O2—Na19.9 (2)O2—Na1—O3i—Na1ii129.16 (10)
O3—S1—O2—Na1iv130.78 (16)O2—Na1—O3ii—Na1vi0.77 (11)
C1—S1—O2—Na1124.82 (19)O2—Na1—O3ii—S1ii164.14 (14)
C1—S1—O2—Na1iv114.29 (18)O2—Na1—O1iii—S1iii38.3 (2)
O1—S1—O3—Na1v26.47 (19)O2—Na1—O2iv—S1iv141.14 (17)
O1—S1—O3—Na1vi171.19 (14)O2—Na1—O2iv—Na1iv0.00 (8)
O2—S1—O3—Na1v102.42 (15)Na1vi—N2—C2—C165.3 (3)
O2—S1—O3—Na1vi59.92 (17)Na1vi—N2—C2—C3110.6 (3)
C1—S1—O3—Na1v141.39 (14)S1—C1—C2—C3173.1 (3)
C1—S1—O3—Na1vi56.26 (17)C6—C1—C2—N2178.1 (3)
O1—S1—C1—C2172.9 (3)C6—C1—C2—C32.1 (5)
O1—S1—C1—C611.8 (3)S1—C1—C2—N22.9 (4)
O2—S1—C1—C251.9 (3)S1—C1—C6—C5174.7 (4)
O2—S1—C1—C6132.9 (3)C2—C1—C6—C50.5 (6)
O3—S1—C1—C267.3 (3)N2—C2—C3—C4177.7 (4)
O3—S1—C1—C6107.9 (3)C1—C2—C3—C41.8 (6)
O3i—Na1—O2—S1130.33 (18)C2—C3—C4—C50.2 (8)
O3i—Na1—O2—Na1iv90.99 (7)C3—C4—C5—C61.8 (9)
O3ii—Na1—O2—S137.53 (19)C4—C5—C6—C11.4 (8)
O3ii—Na1—O2—Na1iv176.21 (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, y1, z; (vi) x+1, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O20.94 (4)2.22 (4)2.901 (3)129 (4)
N2—H2A···O3i0.94 (4)2.52 (4)3.308 (4)142 (4)
N2—H2B···O1vii0.85 (5)2.30 (5)2.942 (3)132 (4)
C6—H6···O10.972.472.871 (5)105
Symmetry codes: (i) x, y+1, z; (vii) x, y+1/2, z+1/2.
 

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