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In the title compound, C6H6NO2+·NH4+·SO42−·NH3SO3, 3-carboxy­pyridinium ions form N—H...O hydrogen-bonded chains along the b axis. Ammonium and sulfate ions and sulfamic acid mol­ecules form a two-dimensional network of hydrogen bonds parallel to (001). This leads to the formation of alternate hydro­philic and hydro­phobic layers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034155/ob2048sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034155/ob2048Isup2.hkl
Contains datablock I

CCDC reference: 624938

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.046
  • wR factor = 0.137
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

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Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact O1A .. C6 .. 2.90 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.93 PLAT213_ALERT_2_C Atom O1A has ADP max/min Ratio ............. 3.60 prola PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S2 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.52
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.926 Tmax scaled 0.925 Tmin scaled 0.841 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC, Mercury (Macrae et al., 2006) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL/PC.

3-Carboxypyridinium ammonium sulfate sulfamic acid solvate top
Crystal data top
C6H6NO2+·NH4+·SO42·NH3SO3Z = 2
Mr = 335.31F(000) = 348
Triclinic, P1Dx = 1.699 Mg m3
Dm = 1.68 Mg m3
Dm measured by flotation in a mixture of xylene and bromoform
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1301 (4) ÅCell parameters from 25 reflections
b = 7.4212 (3) Åθ = 9.9–14.3°
c = 12.5334 (6) ŵ = 0.46 mm1
α = 89.291 (9)°T = 293 K
β = 82.863 (11)°Prism, colourless
γ = 84.845 (10)°0.21 × 0.19 × 0.17 mm
V = 655.39 (6) Å3
Data collection top
MACH3-Nonius
diffractometer
2068 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 25.0°, θmin = 2.8°
ω–2θ scansh = 18
Absorption correction: ψ scan
(North et al., 1968)
k = 88
Tmin = 0.908, Tmax = 0.999l = 1414
2905 measured reflections3 standard reflections every 60 min
2300 independent reflections intensity decay: none
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0802P)2 + 0.8693P]
where P = (Fo2 + 2Fc2)/3
2300 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.73 e Å3
0 restraintsΔρmin = 0.64 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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
N10.7662 (4)0.4629 (3)1.0587 (2)0.0318 (6)
H10.77600.36421.09510.038*
C20.7866 (4)0.6179 (4)1.1071 (2)0.0266 (6)
H20.80980.61911.17850.032*
C30.7727 (4)0.7762 (4)1.0489 (2)0.0263 (6)
C310.7915 (5)0.9533 (4)1.0994 (3)0.0325 (7)
O1A0.7645 (5)1.0931 (3)1.0509 (2)0.0620 (9)
O1B0.8379 (4)0.9414 (3)1.19637 (19)0.0409 (6)
H1B0.84621.04311.21920.061*
C40.7352 (5)0.7708 (4)0.9429 (3)0.0327 (7)
H40.72290.87730.90350.039*
C50.7162 (5)0.6071 (4)0.8962 (3)0.0354 (8)
H50.69340.60160.82490.043*
C60.7315 (5)0.4527 (4)0.9570 (3)0.0344 (7)
H60.71760.34110.92730.041*
N1A0.3722 (5)0.3038 (4)0.4549 (3)0.0420 (8)
H1A0.276 (7)0.267 (6)0.418 (4)0.058 (13)*
H2A0.486 (8)0.335 (7)0.409 (4)0.080 (17)*
H3A0.405 (9)0.218 (9)0.495 (5)0.09 (2)*
H4A0.328 (8)0.402 (8)0.492 (4)0.078 (16)*
S20.09151 (10)0.67064 (9)0.65340 (5)0.0212 (2)
O210.2325 (4)0.6436 (4)0.5586 (2)0.0458 (6)
O220.1859 (4)0.7301 (3)0.7435 (2)0.0430 (6)
O230.0532 (3)0.8131 (3)0.6293 (2)0.0452 (7)
O240.0095 (4)0.5025 (3)0.6824 (2)0.0473 (7)
S10.61527 (11)0.19113 (9)0.69316 (6)0.0268 (2)
N110.8517 (4)0.1879 (3)0.6306 (2)0.0282 (6)
H11A0.91230.26770.66250.042*
H11B0.85180.21660.56140.042*
H11C0.91020.07780.63630.042*
O120.6373 (4)0.1267 (3)0.79888 (19)0.0441 (6)
O130.5478 (4)0.3778 (3)0.6871 (2)0.0424 (6)
O140.5371 (4)0.0731 (3)0.6243 (2)0.0411 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0426 (16)0.0125 (12)0.0397 (15)0.0014 (10)0.0065 (12)0.0043 (10)
C20.0337 (16)0.0159 (14)0.0298 (15)0.0012 (11)0.0054 (12)0.0008 (11)
C30.0373 (17)0.0129 (14)0.0281 (15)0.0018 (11)0.0045 (12)0.0013 (11)
C310.050 (2)0.0165 (15)0.0317 (17)0.0021 (13)0.0086 (14)0.0007 (12)
O1A0.135 (3)0.0113 (12)0.0460 (15)0.0050 (13)0.0360 (17)0.0044 (10)
O1B0.0702 (17)0.0189 (11)0.0370 (13)0.0007 (11)0.0224 (12)0.0016 (9)
C40.050 (2)0.0183 (15)0.0301 (16)0.0007 (13)0.0084 (14)0.0039 (12)
C50.051 (2)0.0260 (16)0.0293 (16)0.0004 (14)0.0068 (14)0.0025 (13)
C60.0418 (18)0.0164 (15)0.0444 (19)0.0018 (13)0.0025 (15)0.0067 (13)
N1A0.0439 (18)0.0217 (15)0.065 (2)0.0001 (13)0.0270 (17)0.0001 (15)
S20.0280 (4)0.0106 (4)0.0257 (4)0.0009 (3)0.0074 (3)0.0013 (3)
O210.0470 (15)0.0478 (15)0.0378 (13)0.0103 (12)0.0032 (11)0.0048 (11)
O220.0721 (18)0.0191 (11)0.0441 (14)0.0039 (11)0.0317 (13)0.0014 (10)
O230.0416 (14)0.0190 (12)0.0776 (19)0.0134 (10)0.0282 (13)0.0091 (11)
O240.0659 (17)0.0245 (13)0.0555 (16)0.0203 (12)0.0124 (13)0.0038 (11)
S10.0349 (4)0.0166 (4)0.0282 (4)0.0033 (3)0.0052 (3)0.0012 (3)
N110.0374 (14)0.0143 (12)0.0323 (14)0.0038 (10)0.0068 (11)0.0004 (10)
O120.0606 (16)0.0388 (14)0.0312 (13)0.0030 (12)0.0051 (11)0.0091 (10)
O130.0484 (15)0.0211 (12)0.0532 (15)0.0140 (10)0.0014 (12)0.0027 (10)
O140.0420 (13)0.0342 (13)0.0491 (15)0.0052 (10)0.0121 (11)0.0065 (11)
Geometric parameters (Å, º) top
N1—C61.333 (4)N1A—H1A0.94 (5)
N1—C21.335 (4)N1A—H2A0.98 (6)
N1—H10.8600N1A—H3A0.84 (7)
C2—C31.377 (4)N1A—H4A0.89 (6)
C2—H20.9300S2—O241.449 (2)
C3—C41.389 (4)S2—O211.462 (3)
C3—C311.491 (4)S2—O231.466 (2)
C31—O1A1.209 (4)S2—O221.475 (2)
C31—O1B1.298 (4)S1—O121.425 (2)
O1B—H1B0.8200S1—O131.430 (2)
C4—C51.379 (4)S1—O141.431 (2)
C4—H40.9300S1—N111.767 (3)
C5—C61.372 (5)N11—H11A0.8900
C5—H50.9300N11—H11B0.8900
C6—H60.9300N11—H11C0.8900
C6—N1—C2123.5 (3)H1A—N1A—H3A108 (5)
C6—N1—H1118.2H2A—N1A—H3A107 (5)
C2—N1—H1118.2H1A—N1A—H4A109 (4)
N1—C2—C3118.5 (3)H2A—N1A—H4A106 (5)
N1—C2—H2120.8H3A—N1A—H4A111 (5)
C3—C2—H2120.8O24—S2—O21109.94 (16)
C2—C3—C4119.6 (3)O24—S2—O23111.61 (16)
C2—C3—C31120.7 (3)O21—S2—O23108.40 (16)
C4—C3—C31119.7 (3)O24—S2—O22109.10 (15)
O1A—C31—O1B125.0 (3)O21—S2—O22108.76 (16)
O1A—C31—C3120.5 (3)O23—S2—O22108.98 (14)
O1B—C31—C3114.5 (3)O12—S1—O13114.83 (15)
C31—O1B—H1B109.5O12—S1—O14116.75 (16)
C5—C4—C3119.8 (3)O13—S1—O14115.12 (16)
C5—C4—H4120.1O12—S1—N11103.07 (14)
C3—C4—H4120.1O13—S1—N11102.73 (14)
C6—C5—C4118.8 (3)O14—S1—N11101.20 (14)
C6—C5—H5120.6S1—N11—H11A109.5
C4—C5—H5120.6S1—N11—H11B109.5
N1—C6—C5119.8 (3)H11A—N11—H11B109.5
N1—C6—H6120.1S1—N11—H11C109.5
C5—C6—H6120.1H11A—N11—H11C109.5
H1A—N1A—H2A115 (4)H11B—N11—H11C109.5
C6—N1—C2—C30.5 (5)C4—C3—C31—O1B176.0 (3)
N1—C2—C3—C41.0 (5)C2—C3—C4—C51.4 (5)
N1—C2—C3—C31179.1 (3)C31—C3—C4—C5179.5 (3)
C2—C3—C31—O1A174.2 (4)C3—C4—C5—C61.2 (5)
C4—C3—C31—O1A3.9 (5)C2—N1—C6—C50.4 (5)
C2—C3—C31—O1B5.9 (5)C4—C5—C6—N10.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1B—H1B···O22i0.821.742.546 (3)167
N1—H1···O1Aii0.862.102.748 (3)131
N1—H1···O22iii0.862.172.889 (4)141
N1A—H1A···O23iv0.94 (5)1.91 (5)2.831 (4)168 (4)
N1A—H2A···O21v0.98 (6)2.11 (6)2.864 (4)132 (4)
N1A—H3A···O140.84 (7)2.19 (7)2.999 (4)160 (6)
N1A—H4A···O210.89 (6)2.01 (6)2.889 (4)172 (5)
N11—H11A···O24vi0.891.962.798 (3)156
N11—H11B···O21v0.891.942.773 (4)155
N11—H11C···O23vii0.891.962.803 (3)158
C6—H6···O1Aii0.932.422.905 (4)113
Symmetry codes: (i) x+1, y+2, z+2; (ii) x, y1, z; (iii) x+1, y+1, z+2; (iv) x, y+1, z+1; (v) x+1, y+1, z+1; (vi) x+1, y, z; (vii) x+1, y1, z.
 

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