2-Carboxyl-atopyridinium-4-nitro-phenol (1/1).

In the title 1:1 adduct, C6H5NO3·C6H5NO2, both mol-ecules are almost planar (r.m.s. deviations for the non-H atoms = 0.027 and 0.023 Å for 4-nitro-phenol and 2-carboxyl-atopyridinium, respectively). The pyridine mol-ecule crystallizes as a zwitterion (nominal proton transfer from the carb-oxy-lic acid group to the N atom in the ring). In the crystal, inversion dimers of the zwitterions linked by pairs of N-H⋯O hydrogen bonds generate R 2 (2)(10) loops; two 4-nitro-phenol mol-ecules link to the dimer by O-H⋯O hydrogen bonds, generating a four-molecule aggregate. These are linked by C-H⋯O inter-actions, forming a three-dimensional network.

Related literature

For a related structure, see: Pandi et al. (2012 ▶).

Experimental

Crystal data

C6H5NO3·C6H5NO2

M = 262.22

Triclinic,

a = 6.1743 (4) Å

b = 7.0512 (3) Å

c = 14.2222 (8) Å

α = 101.727 (3)°

β = 92.191 (2)°

γ = 104.758 (4)°

V = 583.60 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 295 K

0.32 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.963, T max = 0.977

13952 measured reflections

3486 independent reflections

2327 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.130

S = 1.04

3486 reflections

180 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814005650/hb7209sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005650/hb7209Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005650/hb7209Isup3.cml

CCDC reference: 991427

Additional supporting information: crystallographic information; 3D view; checkCIF report

C6H5NO3·C6H5NO2	Z = 2
Mr = 262.22	F(000) = 272
Triclinic, P1	Dx = 1.492 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.1743 (4) Å	Cell parameters from 4728 reflections
b = 7.0512 (3) Å	θ = 2.9–27.7°
c = 14.2222 (8) Å	µ = 0.12 mm−1
α = 101.727 (3)°	T = 295 K
β = 92.191 (2)°	Block, colourless
γ = 104.758 (4)°	0.32 × 0.24 × 0.20 mm
V = 583.60 (6) Å3

Bruker Kappa APEXII CCD diffractometer	3486 independent reflections
Radiation source: fine-focus sealed tube	2327 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scan	θmax = 30.4°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→8
Tmin = 0.963, Tmax = 0.977	k = −10→9
13952 measured reflections	l = −17→20

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0602P)2 + 0.0686P] where P = (Fo2 + 2Fc2)/3
3486 reflections	(Δ/σ)max < 0.001
180 parameters	Δρmax = 0.14 e Å−3
2 restraints	Δρmin = −0.24 e Å−3

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

	x	y	z	Uiso*/Ueq
C1	0.3865 (2)	0.38442 (18)	0.19001 (9)	0.0451 (3)
C2	0.2381 (2)	0.2646 (2)	0.11160 (10)	0.0498 (3)
H2A	0.0853	0.2230	0.1187	0.060*
C3	0.3152 (2)	0.20783 (19)	0.02422 (9)	0.0474 (3)
H3	0.2155	0.1288	−0.0281	0.057*
C4	0.5424 (2)	0.26918 (17)	0.01464 (9)	0.0414 (3)
C5	0.6929 (2)	0.38640 (18)	0.09160 (9)	0.0459 (3)
H5	0.8455	0.4274	0.0840	0.055*
C6	0.6153 (2)	0.44171 (18)	0.17923 (9)	0.0474 (3)
H6	0.7161	0.5179	0.2317	0.057*
C7	0.1820 (2)	0.19479 (19)	0.45093 (8)	0.0429 (3)
C8	−0.1051 (2)	0.1161 (2)	0.32506 (10)	0.0512 (3)
H8	−0.2284	0.1462	0.2981	0.061*
C9	−0.0352 (3)	−0.0443 (2)	0.27958 (10)	0.0550 (3)
H9	−0.1090	−0.1236	0.2211	0.066*
C10	0.1445 (3)	−0.0868 (2)	0.32101 (10)	0.0589 (4)
H10	0.1930	−0.1968	0.2912	0.071*
C11	0.2543 (3)	0.0336 (2)	0.40725 (9)	0.0529 (3)
H11	0.3772	0.0051	0.4356	0.063*
C12	0.2879 (2)	0.3378 (2)	0.54544 (9)	0.0477 (3)
N1	0.6252 (2)	0.21159 (16)	−0.07787 (8)	0.0501 (3)
N2	0.00405 (19)	0.22997 (16)	0.40848 (7)	0.0452 (3)
O1	0.29906 (19)	0.44091 (17)	0.27221 (8)	0.0619 (3)
O2	0.4895 (2)	0.11237 (18)	−0.14600 (7)	0.0689 (3)
O3	0.82814 (19)	0.26305 (17)	−0.08431 (8)	0.0714 (3)
O4	0.2047 (2)	0.47818 (17)	0.57395 (7)	0.0701 (3)
O5	0.44519 (18)	0.29715 (16)	0.58610 (7)	0.0666 (3)
H2	−0.039 (3)	0.3351 (18)	0.4342 (11)	0.066 (5)*
H1	0.400 (3)	0.524 (2)	0.3119 (12)	0.085 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0519 (7)	0.0382 (6)	0.0449 (6)	0.0139 (5)	−0.0003 (5)	0.0071 (5)
C2	0.0394 (6)	0.0514 (7)	0.0550 (7)	0.0101 (5)	−0.0036 (5)	0.0075 (6)
C3	0.0460 (7)	0.0433 (6)	0.0476 (7)	0.0104 (5)	−0.0116 (5)	0.0030 (5)
C4	0.0478 (7)	0.0346 (6)	0.0427 (6)	0.0150 (5)	−0.0034 (5)	0.0066 (5)
C5	0.0404 (6)	0.0410 (6)	0.0525 (7)	0.0091 (5)	−0.0041 (5)	0.0054 (5)
C6	0.0476 (7)	0.0409 (6)	0.0469 (6)	0.0078 (5)	−0.0091 (5)	0.0019 (5)
C7	0.0500 (7)	0.0472 (7)	0.0334 (5)	0.0184 (5)	0.0041 (5)	0.0067 (5)
C8	0.0550 (8)	0.0496 (7)	0.0459 (7)	0.0160 (6)	−0.0074 (6)	0.0034 (5)
C9	0.0678 (9)	0.0471 (7)	0.0443 (7)	0.0161 (6)	−0.0051 (6)	−0.0021 (5)
C10	0.0792 (10)	0.0547 (8)	0.0458 (7)	0.0334 (7)	0.0042 (7)	−0.0016 (6)
C11	0.0617 (8)	0.0616 (8)	0.0412 (6)	0.0335 (7)	0.0005 (6)	0.0039 (6)
C12	0.0572 (8)	0.0530 (7)	0.0350 (5)	0.0238 (6)	0.0008 (5)	0.0034 (5)
N1	0.0602 (7)	0.0435 (6)	0.0477 (6)	0.0192 (5)	−0.0009 (5)	0.0071 (5)
N2	0.0544 (6)	0.0435 (6)	0.0386 (5)	0.0206 (5)	−0.0001 (4)	0.0024 (4)
O1	0.0611 (7)	0.0658 (7)	0.0513 (6)	0.0141 (5)	0.0066 (5)	−0.0004 (5)
O2	0.0762 (7)	0.0787 (7)	0.0460 (6)	0.0263 (6)	−0.0106 (5)	−0.0033 (5)
O3	0.0627 (7)	0.0734 (7)	0.0691 (7)	0.0119 (6)	0.0161 (5)	0.0013 (6)
O4	0.0938 (8)	0.0667 (7)	0.0520 (6)	0.0483 (6)	−0.0173 (5)	−0.0117 (5)
O5	0.0763 (7)	0.0785 (7)	0.0471 (5)	0.0448 (6)	−0.0138 (5)	−0.0082 (5)

C1—O1	1.3363 (16)	C8—N2	1.3349 (16)
C1—C6	1.3902 (19)	C8—C9	1.3626 (19)
C1—C2	1.3934 (18)	C8—H8	0.9300
C2—C3	1.3679 (19)	C9—C10	1.364 (2)
C2—H2A	0.9300	C9—H9	0.9300
C3—C4	1.3796 (18)	C10—C11	1.3801 (19)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.3813 (17)	C11—H11	0.9300
C4—N1	1.4482 (17)	C12—O4	1.2325 (16)
C5—C6	1.3705 (19)	C12—O5	1.2356 (15)
C5—H5	0.9300	N1—O2	1.2222 (15)
C6—H6	0.9300	N1—O3	1.2252 (15)
C7—N2	1.3352 (16)	N2—H2	0.866 (9)
C7—C11	1.3676 (18)	O1—H1	0.838 (9)
C7—C12	1.5156 (17)
O1—C1—C6	123.25 (12)	N2—C8—H8	120.1
O1—C1—C2	117.49 (12)	C9—C8—H8	120.1
C6—C1—C2	119.25 (12)	C8—C9—C10	119.09 (13)
C3—C2—C1	120.57 (12)	C8—C9—H9	120.5
C3—C2—H2A	119.7	C10—C9—H9	120.5
C1—C2—H2A	119.7	C9—C10—C11	119.88 (13)
C2—C3—C4	119.23 (12)	C9—C10—H10	120.1
C2—C3—H3	120.4	C11—C10—H10	120.1
C4—C3—H3	120.4	C7—C11—C10	119.84 (13)
C3—C4—C5	121.20 (12)	C7—C11—H11	120.1
C3—C4—N1	119.62 (11)	C10—C11—H11	120.1
C5—C4—N1	119.18 (12)	O4—C12—O5	127.49 (12)
C6—C5—C4	119.40 (12)	O4—C12—C7	116.64 (11)
C6—C5—H5	120.3	O5—C12—C7	115.84 (11)
C4—C5—H5	120.3	O2—N1—O3	122.83 (12)
C5—C6—C1	120.31 (12)	O2—N1—C4	118.51 (12)
C5—C6—H6	119.8	O3—N1—C4	118.65 (11)
C1—C6—H6	119.8	C8—N2—C7	123.02 (11)
N2—C7—C11	118.38 (11)	C8—N2—H2	117.9 (11)
N2—C7—C12	116.75 (11)	C7—N2—H2	119.0 (11)
C11—C7—C12	124.87 (12)	C1—O1—H1	109.5 (14)
N2—C8—C9	119.78 (13)
O1—C1—C2—C3	177.46 (13)	C12—C7—C11—C10	179.96 (13)
C6—C1—C2—C3	−1.60 (19)	C9—C10—C11—C7	0.2 (2)
C1—C2—C3—C4	0.5 (2)	N2—C7—C12—O4	−1.96 (19)
C2—C3—C4—C5	0.09 (19)	C11—C7—C12—O4	178.60 (14)
C2—C3—C4—N1	−179.33 (11)	N2—C7—C12—O5	176.51 (12)
C3—C4—C5—C6	0.42 (19)	C11—C7—C12—O5	−2.9 (2)
N1—C4—C5—C6	179.84 (11)	C3—C4—N1—O2	1.36 (18)
C4—C5—C6—C1	−1.53 (19)	C5—C4—N1—O2	−178.07 (11)
O1—C1—C6—C5	−176.89 (12)	C3—C4—N1—O3	−178.10 (12)
C2—C1—C6—C5	2.11 (19)	C5—C4—N1—O3	2.47 (18)
N2—C8—C9—C10	0.7 (2)	C9—C8—N2—C7	0.0 (2)
C8—C9—C10—C11	−0.8 (2)	C11—C7—N2—C8	−0.6 (2)
N2—C7—C11—C10	0.5 (2)	C12—C7—N2—C8	179.91 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5i	0.84 (1)	1.77 (1)	2.5929 (15)	165 (2)
N2—H2···O4ii	0.87 (1)	1.88 (1)	2.6693 (15)	151 (2)
C5—H5···O3iii	0.93	2.56	3.3570 (17)	143
C9—H9···O2iv	0.93	2.57	3.2009 (18)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5i	0.84 (1)	1.77 (1)	2.5929 (15)	165 (2)
N2—H2⋯O4ii	0.87 (1)	1.88 (1)	2.6693 (15)	151 (2)
C5—H5⋯O3iii	0.93	2.56	3.3570 (17)	143
C9—H9⋯O2iv	0.93	2.57	3.2009 (18)	126

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .