Benzene-1,3,5-tricarb-oxy-lic acid-5-(pyridin-1-ium-3-yl)-5H-1,2,3,4-tetra-zol-5-ide (1/1).

The asymmetric unit of the title compound, C(6)H(5)N(5)·C(9)H(6)O(6), comprises a full mol-ecule each of neutral trimesic acid (tma) and zwitterionic 5-(pyridin-1-ium-3-yl)-5H-1,2,3,4-tetra-zol-5-ide (ptz). The components are linked into a two-dimensional layer by a combination of O-H⋯O, O-H⋯N, N-H⋯O and N-H⋯N hydrogen bonds parallel to the (10[Formula: see text]) plane. Layers comprising alternating rows of tma and ptz are linked into a three-dimensional network by C-H⋯O and π-π inter-actions between tma and tetra-zolate rings [centroid-centroid distance = 3.763 (2) Å], and between pyridinium and tetra-zolate rings [centroid-centroid distance = 3.745 (2) Å].

Related literature

For crystal engineering studies involving the components of the title compound, see: Lin et al. (2005 ▶); Luo et al. (2005 ▶); Yang et al. (2011 ▶).

Experimental

Crystal data

C6H5N5·C9H6O6

M = 357.29

Triclinic,

a = 7.6596 (8) Å

b = 8.7374 (9) Å

c = 11.3931 (11) Å

α = 94.336 (2)°

β = 95.584 (1)°

γ = 98.465 (2)°

V = 747.46 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 298 K

0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.970, T max = 0.988

7554 measured reflections

2770 independent reflections

2438 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.139

S = 1.24

2770 reflections

248 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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: PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811021490/tk2753sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021490/tk2753Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811021490/tk2753Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H5N5·C9H6O6	Z = 2
Mr = 357.29	F(000) = 368
Triclinic, P1	Dx = 1.587 Mg m−3
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6596 (8) Å	Cell parameters from 2432 reflections
b = 8.7374 (9) Å	θ = 2.4–28.3°
c = 11.3931 (11) Å	µ = 0.13 mm−1
α = 94.336 (2)°	T = 298 K
β = 95.584 (1)°	Block, colourless
γ = 98.465 (2)°	0.16 × 0.12 × 0.10 mm
V = 747.46 (13) Å3

Bruker SMART APEX CCD area-detector diffractometer	2770 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	2438 reflections with I > 2σ(I)
graphite	Rint = 0.028
0.3° wide ω exposures scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −9→9
Tmin = 0.970, Tmax = 0.988	k = −10→10
7554 measured reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.139	w = 1/[σ2(Fo2) + (0.041P)2 + 0.5688P] where P = (Fo2 + 2Fc2)/3
S = 1.24	(Δ/σ)max = 0.005
2770 reflections	Δρmax = 0.24 e Å−3
248 parameters	Δρmin = −0.29 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0

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.

	x	y	z	Uiso*/Ueq
C1	0.0853 (4)	0.4773 (3)	0.3543 (2)	0.0287 (6)
C2	0.1850 (4)	0.6185 (3)	0.3963 (3)	0.0380 (7)
H2	0.2941	0.6226	0.4410	0.046*
C3	−0.0294 (5)	0.7514 (3)	0.3090 (3)	0.0442 (8)
H3	−0.0663	0.8458	0.2951	0.053*
C4	−0.1328 (4)	0.6155 (4)	0.2643 (3)	0.0438 (8)
H4	−0.2406	0.6158	0.2190	0.053*
C5	−0.0751 (4)	0.4771 (3)	0.2873 (3)	0.0378 (7)
H5	−0.1445	0.3833	0.2575	0.045*
C6	0.1461 (4)	0.3330 (3)	0.3868 (2)	0.0271 (6)
C7	0.6435 (4)	0.6942 (3)	0.8877 (2)	0.0287 (6)
C8	0.5465 (4)	0.7376 (3)	0.7906 (3)	0.0306 (6)
H8	0.4858	0.6622	0.7331	0.037*
C9	0.5391 (4)	0.8940 (3)	0.7785 (2)	0.0283 (6)
C10	0.6274 (4)	1.0065 (3)	0.8654 (2)	0.0287 (6)
H10	0.6234	1.1111	0.8571	0.034*
C11	0.7210 (4)	0.9634 (3)	0.9639 (2)	0.0277 (6)
C12	0.7303 (4)	0.8069 (3)	0.9750 (2)	0.0301 (6)
H12	0.7947	0.7779	1.0409	0.036*
C13	0.6573 (4)	0.5263 (3)	0.8965 (2)	0.0324 (7)
C14	0.4369 (4)	0.9377 (3)	0.6711 (2)	0.0313 (7)
C15	0.8122 (4)	1.0852 (3)	1.0584 (2)	0.0295 (6)
N1	0.1243 (4)	0.7486 (3)	0.3726 (3)	0.0456 (7)
H1	0.183 (5)	0.841 (4)	0.401 (3)	0.055*
N2	0.2717 (3)	0.3285 (3)	0.4749 (2)	0.0366 (6)
N3	0.2783 (3)	0.1772 (3)	0.4792 (2)	0.0364 (6)
N4	0.1635 (3)	0.0944 (3)	0.3974 (2)	0.0342 (6)
N5	0.0770 (3)	0.1911 (2)	0.3364 (2)	0.0316 (6)
O1	0.7675 (4)	0.5045 (3)	0.9864 (2)	0.0643 (8)
H1A	0.779 (6)	0.412 (5)	0.993 (4)	0.096*
O2	0.5762 (4)	0.4234 (3)	0.8289 (2)	0.0646 (8)
O3	0.3320 (3)	0.8463 (2)	0.60580 (18)	0.0423 (6)
O4	0.4766 (3)	1.0861 (2)	0.6547 (2)	0.0474 (6)
H4A	0.406 (5)	1.104 (4)	0.589 (4)	0.071*
O5	0.8228 (3)	1.2228 (2)	1.04881 (19)	0.0470 (6)
O6	0.8802 (3)	1.0282 (2)	1.15213 (18)	0.0409 (6)
H6A	0.944 (5)	1.106 (4)	1.214 (3)	0.061*

	U11	U22	U33	U12	U13	U23
C1	0.0376 (16)	0.0218 (14)	0.0248 (14)	0.0026 (12)	−0.0011 (12)	0.0003 (11)
C2	0.0460 (19)	0.0257 (15)	0.0389 (17)	0.0041 (13)	−0.0080 (14)	0.0004 (13)
C3	0.064 (2)	0.0238 (16)	0.0460 (19)	0.0112 (15)	0.0001 (17)	0.0118 (14)
C4	0.051 (2)	0.0391 (18)	0.0425 (19)	0.0149 (15)	−0.0078 (15)	0.0090 (14)
C5	0.0473 (18)	0.0262 (15)	0.0363 (17)	0.0028 (13)	−0.0066 (14)	−0.0003 (12)
C6	0.0311 (15)	0.0237 (14)	0.0254 (14)	0.0029 (11)	−0.0004 (12)	0.0026 (11)
C7	0.0331 (15)	0.0231 (14)	0.0302 (15)	0.0049 (11)	0.0026 (12)	0.0055 (11)
C8	0.0295 (15)	0.0293 (15)	0.0315 (15)	0.0017 (12)	−0.0008 (12)	0.0047 (12)
C9	0.0288 (15)	0.0288 (14)	0.0285 (15)	0.0074 (12)	0.0039 (12)	0.0033 (12)
C10	0.0353 (16)	0.0227 (14)	0.0284 (15)	0.0068 (11)	0.0000 (12)	0.0056 (11)
C11	0.0301 (15)	0.0266 (14)	0.0267 (15)	0.0071 (11)	0.0005 (12)	0.0035 (11)
C12	0.0362 (16)	0.0271 (14)	0.0277 (15)	0.0085 (12)	−0.0034 (12)	0.0086 (11)
C13	0.0412 (17)	0.0260 (15)	0.0293 (16)	0.0048 (13)	−0.0011 (13)	0.0047 (12)
C14	0.0341 (16)	0.0288 (15)	0.0305 (16)	0.0064 (12)	−0.0008 (13)	0.0038 (12)
C15	0.0353 (16)	0.0260 (15)	0.0268 (15)	0.0077 (12)	−0.0034 (12)	0.0026 (11)
N1	0.0549 (18)	0.0200 (13)	0.0564 (18)	−0.0011 (12)	−0.0101 (14)	0.0019 (12)
N2	0.0457 (15)	0.0275 (13)	0.0339 (14)	0.0054 (11)	−0.0084 (12)	0.0032 (10)
N3	0.0462 (15)	0.0286 (13)	0.0332 (14)	0.0087 (11)	−0.0061 (12)	0.0039 (11)
N4	0.0411 (14)	0.0240 (12)	0.0374 (14)	0.0079 (11)	−0.0017 (11)	0.0039 (10)
N5	0.0410 (14)	0.0228 (12)	0.0294 (13)	0.0063 (10)	−0.0063 (11)	0.0030 (10)
O1	0.105 (2)	0.0261 (12)	0.0554 (16)	0.0204 (13)	−0.0349 (15)	0.0024 (11)
O2	0.0873 (19)	0.0271 (12)	0.0693 (17)	0.0070 (12)	−0.0330 (15)	−0.0036 (11)
O3	0.0476 (13)	0.0375 (12)	0.0355 (12)	0.0017 (10)	−0.0160 (10)	−0.0008 (9)
O4	0.0598 (15)	0.0344 (12)	0.0418 (13)	0.0045 (10)	−0.0263 (11)	0.0105 (10)
O5	0.0709 (16)	0.0194 (11)	0.0467 (14)	0.0101 (10)	−0.0186 (11)	0.0025 (9)
O6	0.0589 (14)	0.0245 (11)	0.0344 (12)	0.0056 (10)	−0.0194 (10)	0.0040 (9)

C1—C2	1.377 (4)	C9—C14	1.493 (4)
C1—C5	1.382 (4)	C10—C11	1.379 (4)
C1—C6	1.468 (4)	C10—H10	0.9300
C2—N1	1.326 (4)	C11—C12	1.394 (4)
C2—H2	0.9300	C11—C15	1.497 (4)
C3—N1	1.325 (4)	C12—H12	0.9300
C3—C4	1.360 (4)	C13—O2	1.193 (3)
C3—H3	0.9300	C13—O1	1.307 (4)
C4—C5	1.382 (4)	C14—O3	1.201 (3)
C4—H4	0.9300	C14—O4	1.319 (3)
C5—H5	0.9300	C15—O5	1.207 (3)
C6—N2	1.328 (3)	C15—O6	1.307 (3)
C6—N5	1.337 (3)	N1—H1	0.88 (4)
C7—C8	1.381 (4)	N2—N3	1.335 (3)
C7—C12	1.390 (4)	N3—N4	1.310 (3)
C7—C13	1.496 (4)	N4—N5	1.341 (3)
C8—C9	1.392 (4)	O1—H1A	0.83 (5)
C8—H8	0.9300	O4—H4A	0.92 (4)
C9—C10	1.390 (4)	O6—H6A	0.98 (4)
C2—C1—C5	118.1 (3)	C11—C10—H10	120.0
C2—C1—C6	119.8 (3)	C9—C10—H10	120.0
C5—C1—C6	122.0 (2)	C10—C11—C12	119.9 (2)
N1—C2—C1	119.6 (3)	C10—C11—C15	119.7 (2)
N1—C2—H2	120.2	C12—C11—C15	120.3 (2)
C1—C2—H2	120.2	C7—C12—C11	120.1 (2)
N1—C3—C4	119.7 (3)	C7—C12—H12	120.0
N1—C3—H3	120.2	C11—C12—H12	120.0
C4—C3—H3	120.2	O2—C13—O1	123.6 (3)
C3—C4—C5	118.8 (3)	O2—C13—C7	123.7 (3)
C3—C4—H4	120.6	O1—C13—C7	112.6 (2)
C5—C4—H4	120.6	O3—C14—O4	123.9 (3)
C1—C5—C4	120.4 (3)	O3—C14—C9	123.2 (3)
C1—C5—H5	119.8	O4—C14—C9	112.9 (2)
C4—C5—H5	119.8	O5—C15—O6	123.2 (3)
N2—C6—N5	112.1 (2)	O5—C15—C11	123.3 (2)
N2—C6—C1	123.2 (2)	O6—C15—C11	113.5 (2)
N5—C6—C1	124.6 (2)	C3—N1—C2	123.4 (3)
C8—C7—C12	119.8 (2)	C3—N1—H1	115 (2)
C8—C7—C13	119.6 (2)	C2—N1—H1	122 (2)
C12—C7—C13	120.7 (2)	C6—N2—N3	104.0 (2)
C7—C8—C9	120.2 (3)	N4—N3—N2	110.7 (2)
C7—C8—H8	119.9	N3—N4—N5	108.6 (2)
C9—C8—H8	119.9	C6—N5—N4	104.6 (2)
C10—C9—C8	119.9 (3)	C13—O1—H1A	115 (3)
C10—C9—C14	121.1 (2)	C14—O4—H4A	107 (2)
C8—C9—C14	119.0 (2)	C15—O6—H6A	115 (2)
C11—C10—C9	120.1 (2)
C5—C1—C2—N1	0.7 (4)	C8—C7—C13—O2	−6.8 (5)
C6—C1—C2—N1	−176.0 (3)	C12—C7—C13—O2	174.6 (3)
N1—C3—C4—C5	0.5 (5)	C8—C7—C13—O1	173.4 (3)
C2—C1—C5—C4	−0.4 (5)	C12—C7—C13—O1	−5.2 (4)
C6—C1—C5—C4	176.2 (3)	C10—C9—C14—O3	−165.2 (3)
C3—C4—C5—C1	−0.2 (5)	C8—C9—C14—O3	15.3 (4)
C2—C1—C6—N2	15.2 (4)	C10—C9—C14—O4	16.0 (4)
C5—C1—C6—N2	−161.3 (3)	C8—C9—C14—O4	−163.6 (3)
C2—C1—C6—N5	−168.4 (3)	C10—C11—C15—O5	−7.1 (4)
C5—C1—C6—N5	15.1 (4)	C12—C11—C15—O5	172.9 (3)
C12—C7—C8—C9	1.6 (4)	C10—C11—C15—O6	173.3 (3)
C13—C7—C8—C9	−177.0 (3)	C12—C11—C15—O6	−6.7 (4)
C7—C8—C9—C10	−1.0 (4)	C4—C3—N1—C2	−0.3 (5)
C7—C8—C9—C14	178.5 (3)	C1—C2—N1—C3	−0.4 (5)
C8—C9—C10—C11	−0.5 (4)	N5—C6—N2—N3	−0.6 (3)
C14—C9—C10—C11	180.0 (3)	C1—C6—N2—N3	176.2 (3)
C9—C10—C11—C12	1.4 (4)	C6—N2—N3—N4	0.4 (3)
C9—C10—C11—C15	−178.6 (3)	N2—N3—N4—N5	−0.1 (3)
C8—C7—C12—C11	−0.7 (4)	N2—C6—N5—N4	0.6 (3)
C13—C7—C12—C11	178.0 (3)	C1—C6—N5—N4	−176.2 (3)
C10—C11—C12—C7	−0.8 (4)	N3—N4—N5—C6	−0.3 (3)
C15—C11—C12—C7	179.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4i	0.88 (4)	2.25 (4)	2.981 (3)	141 (3)
N1—H1···O3	0.88 (4)	2.49 (3)	2.958 (3)	114 (3)
O1—H1A···O5ii	0.83 (5)	1.88 (5)	2.694 (3)	165 (5)
O4—H4A···N3i	0.92 (4)	1.73 (4)	2.635 (3)	168 (4)
O6—H6A···N4iii	0.98 (4)	2.57 (4)	3.325 (3)	134 (3)
O6—H6A···N5iii	0.98 (4)	1.70 (4)	2.647 (3)	163 (3)
C3—H3···O6iv	0.93	2.41	3.230 (3)	147.
C4—H4···O2v	0.93	2.54	3.418 (4)	157.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N4i	0.88 (4)	2.25 (4)	2.981 (3)	141 (3)
N1—H1⋯O3	0.88 (4)	2.49 (3)	2.958 (3)	114 (3)
O1—H1A⋯O5ii	0.83 (5)	1.88 (5)	2.694 (3)	165 (5)
O4—H4A⋯N3i	0.92 (4)	1.73 (4)	2.635 (3)	168 (4)
O6—H6A⋯N4iii	0.98 (4)	2.57 (4)	3.325 (3)	134 (3)
O6—H6A⋯N5iii	0.98 (4)	1.70 (4)	2.647 (3)	163 (3)
C3—H3⋯O6iv	0.93	2.41	3.230 (3)	147
C4—H4⋯O2v	0.93	2.54	3.418 (4)	157

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