Benzene-1,3,5-tricarb-oxy-lic acid-5-(4-pyrid-yl)pyrimidine (1/1).

In the pyrimidine mol-ecule of the title compound, C(9)H(7)N(3)·C(9)H(6)O(6), the pyridine ring is oriented at 33.26 (11)° with respect to the pyrimidine ring. In the benzene-1,3,5-tricarb-oxy-lic acid mol-ecule, the three carb-oxy groups are twisted by 7.92 (9), 8.68 (10) and 17.07 (10)° relative to the benzene ring. Classical O-H⋯N and O-H⋯O hydrogen bonds and weak C-H⋯O and C-H⋯N hydrogen bonds occur in the crystal structure.

Related literature

For hydrogen bonding in pyrimidine derivatives, see: Hou et al. (2011 ▶); Horikoshi et al. (2004 ▶); Georgiev et al. (2004 ▶); Santoni et al. (2008 ▶); Huang & Parquette (2000 ▶). For co-crystals of organic acids and pyrimidine, see: Bhogala & Nangia(2003 ▶); Du et al. (2005 ▶); Hou et al. (2008 ▶).

Experimental

Crystal data

C9H7N3·C9H6O6

M = 367.31

Monoclinic,

a = 8.3532 (19) Å

b = 14.865 (3) Å

c = 13.066 (3) Å

β = 98.325 (4)°

V = 1605.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 298 K

0.32 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

8278 measured reflections

2967 independent reflections

2142 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.130

S = 1.04

2967 reflections

256 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811051075/xu5398sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051075/xu5398Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051075/xu5398Isup3.cml

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

C9H7N3·C9H6O6	F(000) = 760
Mr = 367.31	Dx = 1.520 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1381 reflections
a = 8.3532 (19) Å	θ = 2.5–22.7°
b = 14.865 (3) Å	µ = 0.12 mm−1
c = 13.066 (3) Å	T = 298 K
β = 98.325 (4)°	Block, colourless
V = 1605.4 (6) Å3	0.32 × 0.12 × 0.10 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2142 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
graphite	θmax = 25.5°, θmin = 2.1°
φ and ω scans	h = −10→10
8278 measured reflections	k = −18→17
2967 independent reflections	l = −9→15

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)] = 0.055	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) + (0.0605P)2 + 0.0652P] where P = (Fo2 + 2Fc2)/3
2967 reflections	(Δ/σ)max < 0.001
256 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.21 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.

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 > 2sigma(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	1.0045 (3)	0.23487 (15)	0.04299 (17)	0.0307 (5)
C2	0.9253 (3)	0.28752 (14)	0.11876 (16)	0.0298 (5)
C3	0.9233 (3)	0.38061 (15)	0.11112 (17)	0.0328 (6)
H3	0.9717	0.4086	0.0598	0.039*
C4	0.8495 (3)	0.43246 (14)	0.17958 (16)	0.0314 (6)
C5	0.7764 (3)	0.38975 (15)	0.25547 (16)	0.0323 (6)
H5	0.7254	0.4239	0.3009	0.039*
C6	0.7787 (3)	0.29718 (15)	0.26421 (16)	0.0314 (5)
C7	0.8537 (3)	0.24592 (15)	0.19591 (16)	0.0315 (6)
H7	0.8559	0.1836	0.2018	0.038*
C8	0.6958 (3)	0.24978 (16)	0.34319 (17)	0.0327 (6)
C9	0.8432 (3)	0.53210 (16)	0.17124 (18)	0.0402 (6)
C10	0.4491 (3)	0.13542 (17)	0.52900 (19)	0.0462 (7)
H10	0.4782	0.1049	0.4723	0.055*
C11	0.3919 (3)	0.08600 (16)	0.60484 (18)	0.0405 (7)
H11	0.3804	0.0239	0.5985	0.049*
C12	0.3513 (3)	0.13035 (15)	0.69125 (16)	0.0302 (5)
C13	0.3600 (3)	0.22316 (15)	0.69197 (17)	0.0319 (6)
H13	0.3274	0.2556	0.7462	0.038*
C14	0.4171 (3)	0.26728 (16)	0.61198 (17)	0.0361 (6)
H14	0.4224	0.3298	0.6137	0.043*
C15	0.3122 (3)	0.07958 (14)	0.78172 (16)	0.0284 (5)
C16	0.2130 (3)	0.11360 (15)	0.84858 (17)	0.0354 (6)
H16	0.1628	0.1689	0.8337	0.043*
C17	0.2625 (3)	−0.00820 (15)	0.95212 (18)	0.0423 (7)
H17	0.2449	−0.0386	1.0117	0.051*
C18	0.3827 (3)	−0.00268 (15)	0.80969 (18)	0.0402 (6)
H18	0.4496	−0.0283	0.7666	0.048*
N1	0.4653 (2)	0.22434 (14)	0.53205 (15)	0.0398 (5)
N2	0.3604 (3)	−0.04710 (13)	0.89448 (16)	0.0470 (6)
N3	0.1871 (2)	0.06964 (12)	0.93362 (14)	0.0380 (5)
O1	1.0171 (2)	0.14904 (10)	0.06445 (13)	0.0432 (5)
H1	1.071 (4)	0.1197 (19)	0.014 (2)	0.082 (10)*
O2	1.0535 (2)	0.26844 (10)	−0.03140 (12)	0.0392 (5)
O3	0.9472 (3)	0.56310 (13)	0.11264 (15)	0.0621 (7)
H3A	0.930 (4)	0.622 (2)	0.095 (2)	0.088 (11)*
O4	0.7531 (2)	0.57872 (11)	0.21148 (14)	0.0605 (6)
O5	0.6348 (2)	0.30593 (11)	0.40541 (13)	0.0446 (5)
H5A	0.572 (4)	0.276 (2)	0.449 (2)	0.093 (11)*
O6	0.6847 (2)	0.16917 (11)	0.34744 (13)	0.0482 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0310 (14)	0.0294 (13)	0.0331 (13)	0.0002 (10)	0.0093 (11)	−0.0013 (10)
C2	0.0296 (14)	0.0323 (13)	0.0289 (12)	−0.0002 (10)	0.0087 (10)	0.0011 (9)
C3	0.0368 (15)	0.0331 (13)	0.0315 (13)	−0.0010 (10)	0.0153 (11)	0.0037 (9)
C4	0.0343 (15)	0.0328 (13)	0.0285 (13)	0.0029 (10)	0.0096 (11)	0.0016 (9)
C5	0.0340 (14)	0.0378 (14)	0.0270 (12)	0.0016 (11)	0.0108 (11)	−0.0009 (10)
C6	0.0283 (14)	0.0376 (13)	0.0293 (13)	−0.0006 (10)	0.0079 (11)	−0.0004 (10)
C7	0.0337 (14)	0.0290 (12)	0.0330 (13)	−0.0006 (10)	0.0092 (11)	0.0006 (9)
C8	0.0343 (15)	0.0370 (14)	0.0280 (13)	−0.0007 (11)	0.0081 (11)	0.0006 (10)
C9	0.0546 (18)	0.0356 (14)	0.0332 (13)	0.0027 (12)	0.0161 (13)	0.0019 (11)
C10	0.0549 (19)	0.0501 (17)	0.0381 (15)	0.0041 (13)	0.0222 (14)	−0.0040 (12)
C11	0.0529 (18)	0.0337 (14)	0.0379 (14)	0.0006 (12)	0.0168 (13)	−0.0050 (10)
C12	0.0283 (14)	0.0316 (13)	0.0318 (13)	−0.0003 (10)	0.0079 (10)	−0.0017 (9)
C13	0.0343 (15)	0.0319 (13)	0.0311 (13)	0.0005 (10)	0.0107 (11)	0.0001 (10)
C14	0.0379 (15)	0.0329 (13)	0.0391 (14)	−0.0021 (11)	0.0110 (12)	0.0022 (10)
C15	0.0292 (14)	0.0245 (12)	0.0326 (13)	−0.0041 (10)	0.0085 (11)	−0.0022 (9)
C16	0.0399 (16)	0.0287 (12)	0.0404 (14)	0.0026 (10)	0.0149 (12)	0.0027 (10)
C17	0.0608 (19)	0.0314 (13)	0.0384 (14)	−0.0028 (12)	0.0197 (13)	0.0047 (11)
C18	0.0528 (18)	0.0288 (13)	0.0435 (15)	0.0004 (12)	0.0224 (13)	−0.0029 (11)
N1	0.0390 (13)	0.0460 (13)	0.0369 (12)	−0.0002 (10)	0.0142 (10)	0.0045 (9)
N2	0.0670 (17)	0.0312 (11)	0.0483 (13)	0.0081 (10)	0.0269 (12)	0.0056 (9)
N3	0.0478 (14)	0.0334 (11)	0.0365 (12)	0.0016 (10)	0.0192 (10)	0.0021 (9)
O1	0.0601 (13)	0.0291 (9)	0.0477 (11)	0.0043 (8)	0.0320 (10)	0.0012 (7)
O2	0.0541 (12)	0.0323 (9)	0.0365 (10)	0.0032 (8)	0.0249 (9)	0.0041 (7)
O3	0.0953 (17)	0.0323 (11)	0.0711 (14)	0.0013 (10)	0.0537 (13)	0.0090 (9)
O4	0.0866 (16)	0.0362 (10)	0.0679 (14)	0.0151 (10)	0.0422 (12)	−0.0003 (9)
O5	0.0600 (13)	0.0422 (10)	0.0386 (10)	−0.0023 (9)	0.0306 (10)	0.0002 (8)
O6	0.0666 (14)	0.0344 (10)	0.0498 (11)	−0.0034 (9)	0.0288 (10)	0.0039 (8)

C1—O2	1.215 (2)	C11—C12	1.391 (3)
C1—O1	1.307 (3)	C11—H11	0.9300
C1—C2	1.490 (3)	C12—C13	1.381 (3)
C2—C3	1.387 (3)	C12—C15	1.478 (3)
C2—C7	1.390 (3)	C13—C14	1.377 (3)
C3—C4	1.390 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—N1	1.335 (3)
C4—C5	1.391 (3)	C14—H14	0.9300
C4—C9	1.485 (3)	C15—C18	1.383 (3)
C5—C6	1.381 (3)	C15—C16	1.384 (3)
C5—H5	0.9300	C16—N3	1.333 (3)
C6—C7	1.389 (3)	C16—H16	0.9300
C6—C8	1.499 (3)	C17—N2	1.322 (3)
C7—H7	0.9300	C17—N3	1.323 (3)
C8—O6	1.204 (3)	C17—H17	0.9300
C8—O5	1.318 (3)	C18—N2	1.326 (3)
C9—O4	1.199 (3)	C18—H18	0.9300
C9—O3	1.321 (3)	O1—H1	0.95 (3)
C10—N1	1.329 (3)	O3—H3A	0.92 (3)
C10—C11	1.374 (3)	O5—H5A	0.95 (3)
C10—H10	0.9300
O2—C1—O1	123.10 (19)	C10—C11—C12	118.9 (2)
O2—C1—C2	123.3 (2)	C10—C11—H11	120.6
O1—C1—C2	113.59 (18)	C12—C11—H11	120.6
C3—C2—C7	119.60 (19)	C13—C12—C11	117.41 (19)
C3—C2—C1	118.57 (18)	C13—C12—C15	121.45 (18)
C7—C2—C1	121.8 (2)	C11—C12—C15	121.0 (2)
C2—C3—C4	120.57 (19)	C14—C13—C12	119.6 (2)
C2—C3—H3	119.7	C14—C13—H13	120.2
C4—C3—H3	119.7	C12—C13—H13	120.2
C3—C4—C5	119.1 (2)	N1—C14—C13	122.9 (2)
C3—C4—C9	121.33 (19)	N1—C14—H14	118.5
C5—C4—C9	119.52 (19)	C13—C14—H14	118.5
C6—C5—C4	120.8 (2)	C18—C15—C16	115.3 (2)
C6—C5—H5	119.6	C18—C15—C12	121.86 (19)
C4—C5—H5	119.6	C16—C15—C12	122.7 (2)
C5—C6—C7	119.71 (19)	N3—C16—C15	122.1 (2)
C5—C6—C8	121.53 (19)	N3—C16—H16	119.0
C7—C6—C8	118.7 (2)	C15—C16—H16	119.0
C6—C7—C2	120.2 (2)	N2—C17—N3	126.6 (2)
C6—C7—H7	119.9	N2—C17—H17	116.7
C2—C7—H7	119.9	N3—C17—H17	116.7
O6—C8—O5	124.2 (2)	N2—C18—C15	123.7 (2)
O6—C8—C6	123.10 (19)	N2—C18—H18	118.1
O5—C8—C6	112.7 (2)	C15—C18—H18	118.1
O4—C9—O3	124.0 (2)	C10—N1—C14	117.28 (19)
O4—C9—C4	124.2 (2)	C17—N2—C18	115.6 (2)
O3—C9—C4	111.8 (2)	C17—N3—C16	116.78 (19)
N1—C10—C11	123.7 (2)	C1—O1—H1	109.3 (17)
N1—C10—H10	118.1	C9—O3—H3A	113.0 (19)
C11—C10—H10	118.1	C8—O5—H5A	111.9 (18)
O2—C1—C2—C3	−7.5 (3)	C3—C4—C9—O3	−16.2 (3)
O1—C1—C2—C3	172.1 (2)	C5—C4—C9—O3	165.7 (2)
O2—C1—C2—C7	172.3 (2)	N1—C10—C11—C12	−1.5 (4)
O1—C1—C2—C7	−8.1 (3)	C10—C11—C12—C13	4.7 (4)
C7—C2—C3—C4	−0.3 (4)	C10—C11—C12—C15	−171.0 (2)
C1—C2—C3—C4	179.4 (2)	C11—C12—C13—C14	−4.1 (3)
C2—C3—C4—C5	−0.5 (3)	C15—C12—C13—C14	171.5 (2)
C2—C3—C4—C9	−178.7 (2)	C12—C13—C14—N1	0.1 (4)
C3—C4—C5—C6	1.0 (3)	C13—C12—C15—C18	−144.0 (2)
C9—C4—C5—C6	179.2 (2)	C11—C12—C15—C18	31.5 (3)
C4—C5—C6—C7	−0.6 (3)	C13—C12—C15—C16	31.0 (3)
C4—C5—C6—C8	−177.9 (2)	C11—C12—C15—C16	−153.5 (2)
C5—C6—C7—C2	−0.3 (3)	C18—C15—C16—N3	−0.3 (4)
C8—C6—C7—C2	177.1 (2)	C12—C15—C16—N3	−175.5 (2)
C3—C2—C7—C6	0.8 (3)	C16—C15—C18—N2	−0.6 (4)
C1—C2—C7—C6	−179.0 (2)	C12—C15—C18—N2	174.7 (2)
C5—C6—C8—O6	173.9 (2)	C11—C10—N1—C14	−2.5 (4)
C7—C6—C8—O6	−3.5 (4)	C13—C14—N1—C10	3.2 (4)
C5—C6—C8—O5	−4.9 (3)	N3—C17—N2—C18	−0.4 (4)
C7—C6—C8—O5	177.7 (2)	C15—C18—N2—C17	0.9 (4)
C3—C4—C9—O4	162.8 (3)	N2—C17—N3—C16	−0.4 (4)
C5—C4—C9—O4	−15.4 (4)	C15—C16—N3—C17	0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3i	0.95 (3)	1.70 (3)	2.652 (2)	173 (3)
O3—H3A···O2ii	0.92 (3)	1.84 (3)	2.720 (2)	161 (3)
O5—H5A···N1	0.95 (3)	1.68 (3)	2.626 (2)	177 (3)
C3—H3···O3ii	0.93	2.48	3.367 (3)	159
C14—H14···N2iii	0.93	2.59	3.335 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3i	0.95 (3)	1.70 (3)	2.652 (2)	173 (3)
O3—H3A⋯O2ii	0.92 (3)	1.84 (3)	2.720 (2)	161 (3)
O5—H5A⋯N1	0.95 (3)	1.68 (3)	2.626 (2)	177 (3)
C3—H3⋯O3ii	0.93	2.48	3.367 (3)	159
C14—H14⋯N2iii	0.93	2.59	3.335 (3)	137

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