3-Hydroxy­pyridinium 1-carboxy­benzene-3-carboxyl­ate

Liu, C.; Wang, J.-G.; Qu, L.; Zhang, D.; Yao, J.-C.

doi:10.1107/S1600536807016856

3-Hydroxypyridinium 1-carboxybenzene-3-carboxylate

C. Liu, J.-G. Wang, L. Qu, D. Zhang and J.-C. Yao

The asymmetric unit of the title organic salt, C₅H₆NO⁺·C₈H₅O₄⁻, comprises a 3-hydroxypyridinium cation and one singly deprotonated 1,3-benzenedicarboxylic acid anion. The cations and anions are linked by N—H

O and O—H

O hydrogen bonds to form a two-dimensional array.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016856/tk2142sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016856/tk2142Isup2.hkl Contains datablock I

CCDC reference: 647456

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.003 Å
R factor = 0.042
wR factor = 0.123
Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.01
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.05

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

   2 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL.

3-Hydroxypyridinium 1-carboxybenzene-3-carboxylate top

Crystal data top

C₅H₆NO⁺·C₈H₅O₄⁻	F(000) = 544
M_r = 261.23	D_x = 1.496 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1325 reflections
a = 10.2943 (17) Å	θ = 2.6–21.7°
b = 10.9947 (18) Å	µ = 0.12 mm⁻¹
c = 10.4059 (17) Å	T = 291 K
β = 99.963 (2)°	Block, brown
V = 1160.0 (3) Å³	0.26 × 0.15 × 0.09 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2160 independent reflections
Radiation source: fine-focus sealed tube	1337 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
φ and ω scans	θ_max = 25.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.971, T_max = 0.990	k = −13→13
8655 measured reflections	l = −12→12

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0579P)² + 0.0997P] where P = (F_o² + 2F_c²)/3
2160 reflections	(Δ/σ)_max < 0.001
174 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

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

	x	y	z	U_iso*/U_eq
O1	−0.10544 (18)	0.29756 (15)	0.34000 (15)	0.0611 (5)
O2	−0.11457 (18)	0.10446 (14)	0.40551 (14)	0.0554 (5)
H2	−0.1275	0.0909	0.3268	0.083*
O3	0.11938 (16)	−0.01611 (13)	0.83424 (13)	0.0516 (5)
O4	0.13211 (16)	0.11308 (14)	0.99867 (14)	0.0538 (5)
O5	0.35553 (19)	0.80183 (15)	0.34618 (14)	0.0610 (5)
H5	0.3696	0.7428	0.3948	0.092*
N1	0.20698 (18)	0.81675 (17)	0.01150 (17)	0.0472 (5)
H1	0.1771	0.8722	−0.0442	0.057*
C1	−0.0432 (2)	0.25140 (19)	0.56609 (19)	0.0384 (5)
C2	0.0010 (2)	0.16068 (19)	0.65583 (19)	0.0385 (5)
H2A	−0.0053	0.0797	0.6295	0.046*
C3	0.0545 (2)	0.18873 (18)	0.78412 (19)	0.0372 (5)
C4	0.0617 (2)	0.31029 (19)	0.8213 (2)	0.0459 (6)
H4	0.0966	0.3308	0.9071	0.055*
C5	0.0178 (2)	0.4008 (2)	0.7328 (2)	0.0545 (7)
H5A	0.0238	0.4818	0.7590	0.065*
C6	−0.0349 (2)	0.37192 (19)	0.6055 (2)	0.0464 (6)
H6	−0.0650	0.4333	0.5462	0.056*
C7	−0.0913 (2)	0.2222 (2)	0.4263 (2)	0.0441 (6)
C8	0.1053 (2)	0.0902 (2)	0.8795 (2)	0.0402 (5)
C9	0.2006 (2)	0.7012 (2)	−0.0271 (2)	0.0540 (7)
H9	0.1632	0.6809	−0.1122	0.065*
C10	0.2497 (3)	0.6127 (2)	0.0602 (2)	0.0544 (6)
H10	0.2463	0.5315	0.0347	0.065*
C11	0.3042 (2)	0.6443 (2)	0.1856 (2)	0.0468 (6)
H11	0.3398	0.5845	0.2445	0.056*
C12	0.3066 (2)	0.7640 (2)	0.2247 (2)	0.0420 (5)
C13	0.2577 (2)	0.8499 (2)	0.1327 (2)	0.0463 (6)
H13	0.2602	0.9318	0.1555	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0861 (14)	0.0568 (11)	0.0376 (9)	0.0057 (9)	0.0022 (9)	0.0148 (8)
O2	0.0823 (12)	0.0497 (10)	0.0301 (9)	0.0025 (9)	−0.0019 (8)	0.0005 (7)
O3	0.0830 (12)	0.0383 (9)	0.0282 (8)	0.0089 (8)	−0.0055 (8)	0.0019 (7)
O4	0.0773 (12)	0.0529 (10)	0.0262 (9)	0.0027 (8)	−0.0054 (8)	−0.0013 (7)
O5	0.0854 (13)	0.0578 (11)	0.0335 (9)	−0.0101 (10)	−0.0074 (9)	0.0033 (8)
N1	0.0572 (12)	0.0495 (12)	0.0328 (11)	0.0071 (9)	0.0020 (9)	0.0121 (9)
C1	0.0412 (13)	0.0413 (13)	0.0317 (12)	0.0020 (10)	0.0034 (9)	0.0027 (9)
C2	0.0480 (13)	0.0356 (12)	0.0307 (12)	0.0019 (9)	0.0031 (10)	0.0024 (9)
C3	0.0409 (12)	0.0379 (12)	0.0313 (12)	0.0008 (9)	0.0022 (9)	0.0004 (9)
C4	0.0558 (15)	0.0424 (13)	0.0364 (13)	−0.0026 (11)	−0.0009 (11)	−0.0030 (10)
C5	0.0732 (17)	0.0377 (13)	0.0494 (15)	−0.0020 (12)	0.0015 (13)	−0.0024 (11)
C6	0.0569 (15)	0.0376 (13)	0.0438 (14)	0.0027 (11)	0.0063 (11)	0.0073 (10)
C7	0.0505 (14)	0.0448 (14)	0.0362 (13)	0.0079 (11)	0.0050 (10)	0.0057 (10)
C8	0.0465 (13)	0.0440 (13)	0.0277 (12)	−0.0011 (10)	−0.0005 (10)	−0.0003 (10)
C9	0.0656 (17)	0.0613 (17)	0.0319 (13)	0.0042 (13)	−0.0010 (12)	−0.0017 (11)
C10	0.0766 (17)	0.0432 (14)	0.0423 (14)	0.0062 (12)	0.0072 (13)	−0.0011 (11)
C11	0.0578 (15)	0.0447 (14)	0.0365 (13)	0.0091 (11)	0.0044 (11)	0.0114 (10)
C12	0.0473 (14)	0.0478 (14)	0.0298 (12)	−0.0019 (10)	0.0035 (10)	0.0031 (10)
C13	0.0604 (15)	0.0406 (13)	0.0361 (13)	0.0023 (11)	0.0037 (11)	0.0036 (10)

Geometric parameters (Å, º) top

O1—C7	1.212 (2)	C3—C4	1.390 (3)
O2—C7	1.328 (3)	C3—C8	1.501 (3)
O2—H2	0.8200	C4—C5	1.378 (3)
O3—C8	1.277 (2)	C4—H4	0.9300
O4—C8	1.248 (2)	C5—C6	1.379 (3)
O5—C12	1.344 (3)	C5—H5A	0.9300
O5—H5	0.8200	C6—H6	0.9300
N1—C13	1.330 (3)	C9—C10	1.367 (3)
N1—C9	1.331 (3)	C9—H9	0.9300
N1—H1	0.8600	C10—C11	1.373 (3)
C1—C6	1.385 (3)	C10—H10	0.9300
C1—C2	1.388 (3)	C11—C12	1.377 (3)
C1—C7	1.488 (3)	C11—H11	0.9300
C2—C3	1.388 (3)	C12—C13	1.376 (3)
C2—H2A	0.9300	C13—H13	0.9300

C7—O2—H2	109.5	C1—C6—H6	120.0
C12—O5—H5	109.5	O1—C7—O2	123.4 (2)
C13—N1—C9	122.59 (19)	O1—C7—C1	123.7 (2)
C13—N1—H1	118.7	O2—C7—C1	112.94 (18)
C9—N1—H1	118.7	O4—C8—O3	122.11 (19)
C6—C1—C2	119.46 (19)	O4—C8—C3	120.18 (19)
C6—C1—C7	119.25 (19)	O3—C8—C3	117.71 (18)
C2—C1—C7	121.2 (2)	N1—C9—C10	119.1 (2)
C3—C2—C1	121.12 (19)	N1—C9—H9	120.5
C3—C2—H2A	119.4	C10—C9—H9	120.5
C1—C2—H2A	119.4	C9—C10—C11	119.6 (2)
C2—C3—C4	118.35 (19)	C9—C10—H10	120.2
C2—C3—C8	120.70 (18)	C11—C10—H10	120.2
C4—C3—C8	120.95 (19)	C10—C11—C12	120.4 (2)
C5—C4—C3	120.9 (2)	C10—C11—H11	119.8
C5—C4—H4	119.6	C12—C11—H11	119.8
C3—C4—H4	119.6	O5—C12—C13	118.3 (2)
C4—C5—C6	120.3 (2)	O5—C12—C11	123.9 (2)
C4—C5—H5A	119.8	C13—C12—C11	117.7 (2)
C6—C5—H5A	119.8	N1—C13—C12	120.5 (2)
C5—C6—C1	119.9 (2)	N1—C13—H13	119.7
C5—C6—H6	120.0	C12—C13—H13	119.7

C6—C1—C2—C3	−0.6 (3)	C2—C1—C7—O2	14.2 (3)
C7—C1—C2—C3	175.4 (2)	C2—C3—C8—O4	−167.7 (2)
C1—C2—C3—C4	0.6 (3)	C4—C3—C8—O4	13.3 (3)
C1—C2—C3—C8	−178.38 (19)	C2—C3—C8—O3	12.2 (3)
C2—C3—C4—C5	−0.5 (3)	C4—C3—C8—O3	−166.8 (2)
C8—C3—C4—C5	178.5 (2)	C13—N1—C9—C10	−1.0 (4)
C3—C4—C5—C6	0.4 (4)	N1—C9—C10—C11	0.2 (4)
C4—C5—C6—C1	−0.4 (4)	C9—C10—C11—C12	1.7 (4)
C2—C1—C6—C5	0.5 (3)	C10—C11—C12—O5	178.5 (2)
C7—C1—C6—C5	−175.6 (2)	C10—C11—C12—C13	−2.6 (3)
C6—C1—C7—O1	11.6 (3)	C9—N1—C13—C12	0.0 (4)
C2—C1—C7—O1	−164.4 (2)	O5—C12—C13—N1	−179.3 (2)
C6—C1—C7—O2	−169.8 (2)	C11—C12—C13—N1	1.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	1.79	2.649 (2)	177
O5—H5···O4ⁱⁱ	0.82	1.81	2.619 (2)	169
O2—H2···O3ⁱⁱⁱ	0.82	1.88	2.670 (2)	161

Symmetry codes: (i) x, y+1, z−1; (ii) −x+1/2, y+1/2, −z+3/2; (iii) −x, −y, −z+1.

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3-Hydroxy­pyridinium 1-carboxy­benzene-3-carboxyl­ate

Supporting information

Key indicators

checkCIF/PLATON results

3-Hydroxypyridinium 1-carboxybenzene-3-carboxylate