3-Carboxy­pyridinium ammonium sulfate sulfamic acid solvate

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.

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

No syntax errors found



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

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Computing details

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

Crystal data

C6H6NO2^+·NH4^+·SO4^2^−·NH3SO3	Z = 2
Mr = 335.31	F(000) = 348
Triclinic, P1	Dx = 1.699 Mg m^−3 Dm = 1.68 Mg m^−3 Dm measured by flotation in a mixture of xylene and bromoform
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1301 (4) Å	Cell parameters from 25 reflections
b = 7.4212 (3) Å	θ = 9.9–14.3°
c = 12.5334 (6) Å	µ = 0.46 mm^−1
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) Å^3

Data collection

MACH3-Nonius diffractometer	2068 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 25.0°, θmin = 2.8°
ω–2θ scans	h = −1→8
Absorption correction: ψ scan (North et al., 1968)	k = −8→8
Tmin = 0.908, Tmax = 0.999	l = −14→14
2905 measured reflections	3 standard reflections every 60 min
2300 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0802P)^2 + 0.8693P] where P = (Fo^2 + 2Fc^2)/3
2300 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.73 e Å^−3
0 restraints	Δρmin = −0.64 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.7662 (4)	0.4629 (3)	1.0587 (2)	0.0318 (6)
H1	0.7760	0.3642	1.0951	0.038*
C2	0.7866 (4)	0.6179 (4)	1.1071 (2)	0.0266 (6)
H2	0.8098	0.6191	1.1785	0.032*
C3	0.7727 (4)	0.7762 (4)	1.0489 (2)	0.0263 (6)
C31	0.7915 (5)	0.9533 (4)	1.0994 (3)	0.0325 (7)
O1A	0.7645 (5)	1.0931 (3)	1.0509 (2)	0.0620 (9)
O1B	0.8379 (4)	0.9414 (3)	1.19637 (19)	0.0409 (6)
H1B	0.8462	1.0431	1.2192	0.061*
C4	0.7352 (5)	0.7708 (4)	0.9429 (3)	0.0327 (7)
H4	0.7229	0.8773	0.9035	0.039*
C5	0.7162 (5)	0.6071 (4)	0.8962 (3)	0.0354 (8)
H5	0.6934	0.6016	0.8249	0.043*
C6	0.7315 (5)	0.4527 (4)	0.9570 (3)	0.0344 (7)
H6	0.7176	0.3411	0.9273	0.041*
N1A	0.3722 (5)	0.3038 (4)	0.4549 (3)	0.0420 (8)
H1A	0.276 (7)	0.267 (6)	0.418 (4)	0.058 (13)*
H2A	0.486 (8)	0.335 (7)	0.409 (4)	0.080 (17)*
H3A	0.405 (9)	0.218 (9)	0.495 (5)	0.09 (2)*
H4A	0.328 (8)	0.402 (8)	0.492 (4)	0.078 (16)*
S2	0.09151 (10)	0.67064 (9)	0.65340 (5)	0.0212 (2)
O21	0.2325 (4)	0.6436 (4)	0.5586 (2)	0.0458 (6)
O22	0.1859 (4)	0.7301 (3)	0.7435 (2)	0.0430 (6)
O23	−0.0532 (3)	0.8131 (3)	0.6293 (2)	0.0452 (7)
O24	0.0095 (4)	0.5025 (3)	0.6824 (2)	0.0473 (7)
S1	0.61527 (11)	0.19113 (9)	0.69316 (6)	0.0268 (2)
N11	0.8517 (4)	0.1879 (3)	0.6306 (2)	0.0282 (6)
H11A	0.9123	0.2677	0.6625	0.042*
H11B	0.8518	0.2166	0.5614	0.042*
H11C	0.9102	0.0778	0.6363	0.042*
O12	0.6373 (4)	0.1267 (3)	0.79888 (19)	0.0441 (6)
O13	0.5478 (4)	0.3778 (3)	0.6871 (2)	0.0424 (6)
O14	0.5371 (4)	0.0731 (3)	0.6243 (2)	0.0411 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0426 (16)	0.0125 (12)	0.0397 (15)	0.0014 (10)	−0.0065 (12)	0.0043 (10)
C2	0.0337 (16)	0.0159 (14)	0.0298 (15)	0.0012 (11)	−0.0054 (12)	0.0008 (11)
C3	0.0373 (17)	0.0129 (14)	0.0281 (15)	0.0018 (11)	−0.0045 (12)	0.0013 (11)
C31	0.050 (2)	0.0165 (15)	0.0317 (17)	−0.0021 (13)	−0.0086 (14)	−0.0007 (12)
O1A	0.135 (3)	0.0113 (12)	0.0460 (15)	−0.0050 (13)	−0.0360 (17)	0.0044 (10)
O1B	0.0702 (17)	0.0189 (11)	0.0370 (13)	−0.0007 (11)	−0.0224 (12)	−0.0016 (9)
C4	0.050 (2)	0.0183 (15)	0.0301 (16)	0.0007 (13)	−0.0084 (14)	0.0039 (12)
C5	0.051 (2)	0.0260 (16)	0.0293 (16)	−0.0004 (14)	−0.0068 (14)	−0.0025 (13)
C6	0.0418 (18)	0.0164 (15)	0.0444 (19)	−0.0018 (13)	−0.0025 (15)	−0.0067 (13)
N1A	0.0439 (18)	0.0217 (15)	0.065 (2)	−0.0001 (13)	−0.0270 (17)	−0.0001 (15)
S2	0.0280 (4)	0.0106 (4)	0.0257 (4)	0.0009 (3)	−0.0074 (3)	−0.0013 (3)
O21	0.0470 (15)	0.0478 (15)	0.0378 (13)	0.0103 (12)	0.0032 (11)	0.0048 (11)
O22	0.0721 (18)	0.0191 (11)	0.0441 (14)	−0.0039 (11)	−0.0317 (13)	−0.0014 (10)
O23	0.0416 (14)	0.0190 (12)	0.0776 (19)	0.0134 (10)	−0.0282 (13)	−0.0091 (11)
O24	0.0659 (17)	0.0245 (13)	0.0555 (16)	−0.0203 (12)	−0.0124 (13)	0.0038 (11)
S1	0.0349 (4)	0.0166 (4)	0.0282 (4)	0.0033 (3)	−0.0052 (3)	0.0012 (3)
N11	0.0374 (14)	0.0143 (12)	0.0323 (14)	0.0038 (10)	−0.0068 (11)	−0.0004 (10)
O12	0.0606 (16)	0.0388 (14)	0.0312 (13)	0.0030 (12)	−0.0051 (11)	0.0091 (10)
O13	0.0484 (15)	0.0211 (12)	0.0532 (15)	0.0140 (10)	−0.0014 (12)	0.0027 (10)
O14	0.0420 (13)	0.0342 (13)	0.0491 (15)	−0.0052 (10)	−0.0121 (11)	−0.0065 (11)

Geometric parameters (Å, º)

N1—C6	1.333 (4)	N1A—H1A	0.94 (5)
N1—C2	1.335 (4)	N1A—H2A	0.98 (6)
N1—H1	0.8600	N1A—H3A	0.84 (7)
C2—C3	1.377 (4)	N1A—H4A	0.89 (6)
C2—H2	0.9300	S2—O24	1.449 (2)
C3—C4	1.389 (4)	S2—O21	1.462 (3)
C3—C31	1.491 (4)	S2—O23	1.466 (2)
C31—O1A	1.209 (4)	S2—O22	1.475 (2)
C31—O1B	1.298 (4)	S1—O12	1.425 (2)
O1B—H1B	0.8200	S1—O13	1.430 (2)
C4—C5	1.379 (4)	S1—O14	1.431 (2)
C4—H4	0.9300	S1—N11	1.767 (3)
C5—C6	1.372 (5)	N11—H11A	0.8900
C5—H5	0.9300	N11—H11B	0.8900
C6—H6	0.9300	N11—H11C	0.8900
C6—N1—C2	123.5 (3)	H1A—N1A—H3A	108 (5)
C6—N1—H1	118.2	H2A—N1A—H3A	107 (5)
C2—N1—H1	118.2	H1A—N1A—H4A	109 (4)
N1—C2—C3	118.5 (3)	H2A—N1A—H4A	106 (5)
N1—C2—H2	120.8	H3A—N1A—H4A	111 (5)
C3—C2—H2	120.8	O24—S2—O21	109.94 (16)
C2—C3—C4	119.6 (3)	O24—S2—O23	111.61 (16)
C2—C3—C31	120.7 (3)	O21—S2—O23	108.40 (16)
C4—C3—C31	119.7 (3)	O24—S2—O22	109.10 (15)
O1A—C31—O1B	125.0 (3)	O21—S2—O22	108.76 (16)
O1A—C31—C3	120.5 (3)	O23—S2—O22	108.98 (14)
O1B—C31—C3	114.5 (3)	O12—S1—O13	114.83 (15)
C31—O1B—H1B	109.5	O12—S1—O14	116.75 (16)
C5—C4—C3	119.8 (3)	O13—S1—O14	115.12 (16)
C5—C4—H4	120.1	O12—S1—N11	103.07 (14)
C3—C4—H4	120.1	O13—S1—N11	102.73 (14)
C6—C5—C4	118.8 (3)	O14—S1—N11	101.20 (14)
C6—C5—H5	120.6	S1—N11—H11A	109.5
C4—C5—H5	120.6	S1—N11—H11B	109.5
N1—C6—C5	119.8 (3)	H11A—N11—H11B	109.5
N1—C6—H6	120.1	S1—N11—H11C	109.5
C5—C6—H6	120.1	H11A—N11—H11C	109.5
H1A—N1A—H2A	115 (4)	H11B—N11—H11C	109.5
C6—N1—C2—C3	−0.5 (5)	C4—C3—C31—O1B	−176.0 (3)
N1—C2—C3—C4	1.0 (5)	C2—C3—C4—C5	−1.4 (5)
N1—C2—C3—C31	179.1 (3)	C31—C3—C4—C5	−179.5 (3)
C2—C3—C31—O1A	−174.2 (4)	C3—C4—C5—C6	1.2 (5)
C4—C3—C31—O1A	3.9 (5)	C2—N1—C6—C5	0.4 (5)
C2—C3—C31—O1B	5.9 (5)	C4—C5—C6—N1	−0.8 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H1B···O22^i	0.82	1.74	2.546 (3)	167
N1—H1···O1A^ii	0.86	2.10	2.748 (3)	131
N1—H1···O22^iii	0.86	2.17	2.889 (4)	141
N1A—H1A···O23^iv	0.94 (5)	1.91 (5)	2.831 (4)	168 (4)
N1A—H2A···O21^v	0.98 (6)	2.11 (6)	2.864 (4)	132 (4)
N1A—H3A···O14	0.84 (7)	2.19 (7)	2.999 (4)	160 (6)
N1A—H4A···O21	0.89 (6)	2.01 (6)	2.889 (4)	172 (5)
N11—H11A···O24^vi	0.89	1.96	2.798 (3)	156
N11—H11B···O21^v	0.89	1.94	2.773 (4)	155
N11—H11C···O23^vii	0.89	1.96	2.803 (3)	158
C6—H6···O1A^ii	0.93	2.42	2.905 (4)	113

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) x, y−1, 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, y−1, z.