Pyridinium 4-carb­oxy-2-nitro­benzoate

In the title compound, C₅H₆N⁺·C₈H₄NO₆⁻, N—H...O and O—H...O hydrogen bonds stabilize the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.027
• wR factor = 0.067
• Data-to-parameter ratio = 6.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT089_ALERT_3_B Poor Data / Parameter Ratio (Zmax .LT. 18) .....       5.98

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O5     -   N1      ..       5.11 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.32

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.02
           From the CIF: _reflns_number_total               1149
           Count of symmetry unique reflns         1149
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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: SMART (Bruker 1997); cell refinement: SAINT (Bruker 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Pyridinium 4-carboxy-2-nitrobenzoate

Crystal data

C5H6N^+·C8H4NO6^−	F(000) = 600
Mr = 290.23	Dx = 1.481 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1799 reflections
a = 14.607 (4) Å	θ = 2.8–26.4°
b = 11.904 (4) Å	µ = 0.12 mm^−1
c = 9.257 (3) Å	T = 294 K
β = 126.051 (4)°	Block, colorless
V = 1301.4 (7) Å^3	0.24 × 0.20 × 0.16 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	1149 independent reflections
Radiation source: fine-focus sealed tube	1053 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.974, Tmax = 0.982	k = −11→14
3262 measured reflections	l = −10→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.027	H-atom parameters constrained
wR(F^2) = 0.067	w = 1/[σ^2(Fo^2) + (0.0378P)^2 + 0.1688P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1149 reflections	Δρmax = 0.13 e Å^−3
192 parameters	Δρmin = −0.13 e Å^−3
2 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0075 (12)

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
O1	0.34839 (15)	0.68738 (15)	0.4864 (2)	0.0442 (5)
C1	0.37193 (18)	0.7427 (2)	0.6190 (3)	0.0315 (6)
O2	0.34012 (16)	0.84036 (16)	0.6202 (2)	0.0443 (5)
C2	0.45164 (18)	0.6876 (2)	0.8014 (3)	0.0296 (5)
C3	0.5404 (2)	0.7485 (2)	0.9428 (3)	0.0335 (6)
H3	0.5478	0.8244	0.9279	0.040*
C4	0.6186 (2)	0.6975 (2)	1.1068 (3)	0.0354 (6)
H4	0.6774	0.7397	1.2003	0.043*
C5	0.60948 (19)	0.5847 (2)	1.1321 (3)	0.0301 (5)
C8	0.6950 (2)	0.5333 (2)	1.3128 (3)	0.0346 (6)
O3	0.75789 (19)	0.59130 (17)	1.4425 (3)	0.0555 (6)
O4	0.69481 (16)	0.42348 (15)	1.3135 (2)	0.0461 (5)
H3A	0.7441	0.4007	1.4144	0.069*
C6	0.5216 (2)	0.5209 (2)	0.9931 (3)	0.0316 (5)
H6	0.5146	0.4449	1.0081	0.038*
C7	0.44469 (18)	0.57431 (19)	0.8314 (3)	0.0293 (5)
N1	0.34737 (18)	0.50730 (19)	0.6903 (3)	0.0390 (6)
O5	0.25255 (14)	0.54740 (17)	0.6196 (3)	0.0542 (6)
O6	0.36570 (19)	0.41538 (19)	0.6535 (3)	0.0632 (6)
C9	0.0961 (2)	0.5810 (2)	0.1734 (3)	0.0443 (7)
H9	0.1245	0.5468	0.2825	0.053*
N2	0.15243 (19)	0.6659 (2)	0.1667 (3)	0.0448 (6)
H2	0.2144	0.6880	0.2638	0.054*
C10	−0.0027 (2)	0.5432 (3)	0.0232 (4)	0.0471 (7)
H10	−0.0418	0.4835	0.0283	0.056*
C11	−0.0431 (2)	0.5958 (3)	−0.1368 (4)	0.0519 (8)
H11	−0.1104	0.5718	−0.2413	0.062*
C12	0.0157 (3)	0.6829 (3)	−0.1416 (4)	0.0543 (8)
H12	−0.0116	0.7186	−0.2492	0.065*
C13	0.1157 (3)	0.7180 (3)	0.0136 (4)	0.0525 (8)
H13	0.1569	0.7768	0.0117	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0435 (10)	0.0466 (11)	0.0265 (9)	0.0029 (8)	0.0118 (8)	0.0056 (8)
C1	0.0213 (11)	0.0351 (14)	0.0268 (12)	0.0007 (10)	0.0079 (10)	0.0099 (11)
O2	0.0441 (10)	0.0401 (11)	0.0315 (10)	0.0143 (9)	0.0128 (8)	0.0146 (8)
C2	0.0238 (11)	0.0337 (14)	0.0251 (11)	0.0046 (9)	0.0109 (10)	0.0093 (9)
C3	0.0327 (12)	0.0274 (13)	0.0304 (12)	0.0018 (11)	0.0131 (10)	0.0069 (11)
C4	0.0309 (12)	0.0357 (14)	0.0279 (12)	0.0004 (10)	0.0108 (11)	0.0019 (10)
C5	0.0273 (12)	0.0331 (13)	0.0228 (11)	0.0076 (10)	0.0109 (10)	0.0072 (9)
C8	0.0317 (12)	0.0372 (15)	0.0237 (12)	0.0098 (11)	0.0100 (11)	0.0059 (11)
O3	0.0590 (12)	0.0432 (12)	0.0273 (10)	0.0122 (10)	0.0047 (9)	0.0041 (9)
O4	0.0458 (11)	0.0353 (11)	0.0273 (9)	0.0094 (8)	0.0050 (9)	0.0104 (8)
C6	0.0290 (11)	0.0290 (13)	0.0288 (12)	0.0045 (10)	0.0126 (10)	0.0082 (10)
C7	0.0220 (11)	0.0319 (13)	0.0237 (12)	0.0019 (9)	0.0078 (10)	0.0051 (10)
N1	0.0336 (12)	0.0396 (14)	0.0274 (11)	−0.0067 (10)	0.0088 (9)	0.0075 (9)
O5	0.0236 (9)	0.0591 (13)	0.0505 (12)	−0.0015 (9)	0.0056 (8)	0.0150 (10)
O6	0.0606 (15)	0.0457 (13)	0.0562 (13)	−0.0067 (11)	0.0194 (12)	−0.0132 (10)
C9	0.0423 (16)	0.0518 (18)	0.0353 (15)	0.0085 (13)	0.0209 (14)	0.0033 (13)
N2	0.0371 (11)	0.0456 (14)	0.0367 (12)	−0.0008 (10)	0.0134 (10)	−0.0123 (11)
C10	0.0378 (15)	0.0533 (18)	0.0472 (16)	−0.0027 (12)	0.0234 (13)	−0.0041 (13)
C11	0.0355 (15)	0.070 (2)	0.0335 (15)	0.0040 (15)	0.0111 (12)	−0.0086 (14)
C12	0.0611 (19)	0.059 (2)	0.0372 (15)	0.0196 (17)	0.0258 (14)	0.0131 (13)
C13	0.0602 (18)	0.0405 (16)	0.0571 (19)	0.0036 (14)	0.0347 (17)	0.0001 (14)

Geometric parameters (Å, º)

O1—C1	1.250 (3)	C7—N1	1.476 (3)
C1—O2	1.255 (3)	N1—O6	1.222 (3)
C1—C2	1.524 (3)	N1—O5	1.228 (3)
C2—C3	1.387 (3)	C9—N2	1.328 (4)
C2—C7	1.392 (3)	C9—C10	1.363 (4)
C3—C4	1.391 (3)	C9—H9	0.9300
C3—H3	0.9300	N2—C13	1.336 (4)
C4—C5	1.383 (4)	N2—H2	0.8600
C4—H4	0.9300	C10—C11	1.380 (5)
C5—C6	1.391 (4)	C10—H10	0.9300
C5—C8	1.507 (3)	C11—C12	1.363 (4)
C8—O3	1.210 (3)	C11—H11	0.9300
C8—O4	1.307 (3)	C12—C13	1.380 (4)
O4—H3A	0.8200	C12—H12	0.9300
C6—C7	1.389 (3)	C13—H13	0.9300
C6—H6	0.9300
O1—C1—O2	127.4 (2)	C6—C7—N1	117.0 (2)
O1—C1—C2	116.8 (2)	C2—C7—N1	119.50 (19)
O2—C1—C2	115.8 (2)	O6—N1—O5	124.3 (2)
C3—C2—C7	117.1 (2)	O6—N1—C7	118.4 (2)
C3—C2—C1	120.1 (2)	O5—N1—C7	117.3 (2)
C7—C2—C1	122.7 (2)	N2—C9—C10	121.1 (3)
C2—C3—C4	120.9 (2)	N2—C9—H9	119.4
C2—C3—H3	119.6	C10—C9—H9	119.4
C4—C3—H3	119.6	C9—N2—C13	122.0 (2)
C5—C4—C3	120.6 (2)	C9—N2—H2	119.0
C5—C4—H4	119.7	C13—N2—H2	119.0
C3—C4—H4	119.7	C9—C10—C11	118.2 (3)
C4—C5—C6	120.1 (2)	C9—C10—H10	120.9
C4—C5—C8	118.9 (2)	C11—C10—H10	120.9
C6—C5—C8	121.0 (2)	C12—C11—C10	120.0 (3)
O3—C8—O4	124.6 (2)	C12—C11—H11	120.0
O3—C8—C5	121.2 (2)	C10—C11—H11	120.0
O4—C8—C5	114.1 (2)	C11—C12—C13	119.9 (3)
C8—O4—H3A	109.5	C11—C12—H12	120.1
C7—C6—C5	117.9 (2)	C13—C12—H12	120.1
C7—C6—H6	121.1	N2—C13—C12	118.8 (3)
C5—C6—H6	121.1	N2—C13—H13	120.6
C6—C7—C2	123.4 (2)	C12—C13—H13	120.6
O1—C1—C2—C3	134.4 (2)	C5—C6—C7—N1	−175.5 (2)
O2—C1—C2—C3	−43.5 (3)	C3—C2—C7—C6	−0.3 (3)
O1—C1—C2—C7	−40.9 (3)	C1—C2—C7—C6	175.1 (2)
O2—C1—C2—C7	141.1 (2)	C3—C2—C7—N1	175.5 (2)
C7—C2—C3—C4	0.0 (3)	C1—C2—C7—N1	−9.0 (3)
C1—C2—C3—C4	−175.6 (2)	C6—C7—N1—O6	−50.7 (3)
C2—C3—C4—C5	0.2 (4)	C2—C7—N1—O6	133.2 (3)
C3—C4—C5—C6	−0.1 (4)	C6—C7—N1—O5	128.0 (2)
C3—C4—C5—C8	−179.1 (2)	C2—C7—N1—O5	−48.1 (3)
C4—C5—C8—O3	13.2 (4)	C10—C9—N2—C13	−0.2 (4)
C6—C5—C8—O3	−165.8 (3)	N2—C9—C10—C11	−0.2 (4)
C4—C5—C8—O4	−165.9 (2)	C9—C10—C11—C12	0.2 (4)
C6—C5—C8—O4	15.1 (4)	C10—C11—C12—C13	0.2 (5)
C4—C5—C6—C7	−0.2 (4)	C9—N2—C13—C12	0.6 (4)
C8—C5—C6—C7	178.8 (2)	C11—C12—C13—N2	−0.6 (4)
C5—C6—C7—C2	0.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.82	2.655 (3)	162
O4—H3A···O2^i	0.82	1.72	2.540 (2)	174

Symmetry code: (i) x+1/2, y−1/2, z+1.