2-Amino-4,6-dimethyl-pyrimidine-benzoic acid (1/1).

The crystal of the title compound, C(6)H(9)N(3)·C(7)H(6)O(2), contains tetra-meric hydrogen-bonded units comprising a central pair of 2-amino-pyrimidine mol-ecules linked across a centre of inversion by N-H⋯N hydrogen bonds and two pendant benzoic acid mol-ecules attached through N-H⋯O and O-H⋯N hydrogen bonds. These hydrogen-bonded units are arranged into layers in (002).

Related literature

For the biological activity of pyrimidine and amino­pyrimidine derivatives, see: Hunt et al. (1980 ▶); Baker & Santi (1965 ▶). For related structures, see: Skovsgaard & Bond (2009 ▶); Fun et al. (2006 ▶); Wang et al. (2007 ▶); Schwalbe & Williams (1982 ▶); Hu et al. (2002 ▶); Chinnakali et al. (1999 ▶).

Experimental

Crystal data

C6H9N3·C7H6O2

M = 245.28

Monoclinic,

a = 6.7019 (9) Å

b = 7.6466 (10) Å

c = 25.285 (3) Å

β = 91.360 (2)°

V = 1295.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.18 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.985, T max = 0.991

6594 measured reflections

2273 independent reflections

1228 reflections with I > 2σ(I)

R int = 0.104

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.137

S = 1.01

2273 reflections

167 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020649/bi2374sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020649/bi2374Isup2.hkl

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

C6H9N3·C7H6O2	F(000) = 520
Mr = 245.28	Dx = 1.258 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 167 reflections
a = 6.7019 (9) Å	θ = 1.6–25.0°
b = 7.6466 (10) Å	µ = 0.09 mm−1
c = 25.285 (3) Å	T = 295 K
β = 91.360 (2)°	Block, colourless
V = 1295.4 (3) Å3	0.18 × 0.15 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	2273 independent reflections
Radiation source: fine-focus sealed tube	1228 reflections with I > 2σ(I)
graphite	Rint = 0.104
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.985, Tmax = 0.991	k = −9→9
6594 measured reflections	l = −22→30

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)] = 0.053	H-atom parameters constrained
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0352P)2 + 0.012P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2273 reflections	Δρmax = 0.22 e Å−3
167 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0077 (16)

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
O1	0.6583 (2)	0.6591 (2)	0.41923 (6)	0.0678 (5)
H1	0.5870	0.7100	0.4402	0.102*
O2	0.3940 (3)	0.6933 (3)	0.36625 (7)	0.0787 (6)
N1	0.4633 (3)	0.7645 (2)	0.50129 (7)	0.0482 (5)
N2	0.1976 (3)	0.9074 (2)	0.54612 (8)	0.0560 (6)
N3	0.1836 (3)	0.8632 (2)	0.45633 (8)	0.0646 (6)
H3A	0.2332	0.8250	0.4275	0.078*
H3B	0.0689	0.9137	0.4557	0.078*
C1	0.6891 (4)	0.5714 (3)	0.33125 (9)	0.0540 (6)
C2	0.8886 (4)	0.5334 (3)	0.34037 (10)	0.0662 (7)
H2	0.9484	0.5593	0.3730	0.079*
C3	0.9993 (5)	0.4573 (4)	0.30126 (13)	0.0813 (9)
H3	1.1337	0.4326	0.3075	0.098*
C4	0.9124 (6)	0.4184 (4)	0.25352 (13)	0.0892 (10)
H4	0.9866	0.3641	0.2276	0.107*
C5	0.7167 (6)	0.4587 (4)	0.24346 (11)	0.0931 (10)
H5	0.6586	0.4332	0.2106	0.112*
C6	0.6032 (4)	0.5382 (4)	0.28248 (10)	0.0754 (8)
H6	0.4708	0.5683	0.2754	0.090*
C7	0.5664 (4)	0.6473 (3)	0.37388 (10)	0.0542 (7)
C8	0.2837 (4)	0.8443 (3)	0.50166 (10)	0.0497 (6)
C9	0.5618 (3)	0.7431 (3)	0.54739 (9)	0.0522 (6)
C10	0.4805 (4)	0.8019 (3)	0.59401 (10)	0.0620 (7)
H10	0.5481	0.7868	0.6262	0.074*
C11	0.2973 (4)	0.8831 (3)	0.59146 (10)	0.0579 (7)
C12	0.7598 (4)	0.6537 (3)	0.54573 (11)	0.0699 (8)
H12A	0.7401	0.5309	0.5397	0.105*
H12B	0.8303	0.6706	0.5788	0.105*
H12C	0.8361	0.7022	0.5176	0.105*
C13	0.1975 (4)	0.9484 (3)	0.64045 (10)	0.0793 (9)
H13A	0.1886	1.0737	0.6393	0.119*
H13B	0.2743	0.9136	0.6712	0.119*
H13C	0.0658	0.8996	0.6421	0.119*

	U11	U22	U33	U12	U13	U23
O1	0.0593 (11)	0.0969 (15)	0.0473 (11)	0.0084 (10)	0.0053 (9)	−0.0141 (10)
O2	0.0568 (12)	0.1232 (16)	0.0564 (12)	0.0167 (11)	0.0055 (9)	−0.0012 (10)
N1	0.0425 (11)	0.0546 (12)	0.0480 (12)	−0.0031 (9)	0.0092 (9)	−0.0005 (9)
N2	0.0584 (13)	0.0594 (13)	0.0510 (13)	−0.0063 (10)	0.0179 (10)	−0.0042 (11)
N3	0.0552 (13)	0.0919 (16)	0.0472 (13)	0.0168 (11)	0.0084 (10)	−0.0057 (11)
C1	0.0620 (17)	0.0566 (15)	0.0439 (15)	−0.0070 (13)	0.0109 (12)	0.0003 (12)
C2	0.0670 (19)	0.0707 (18)	0.0617 (17)	−0.0002 (14)	0.0157 (14)	−0.0015 (14)
C3	0.081 (2)	0.085 (2)	0.080 (2)	0.0071 (17)	0.0337 (18)	−0.0012 (18)
C4	0.119 (3)	0.073 (2)	0.078 (2)	−0.003 (2)	0.056 (2)	−0.0027 (18)
C5	0.119 (3)	0.113 (3)	0.0486 (19)	−0.020 (2)	0.0181 (18)	−0.0134 (17)
C6	0.0767 (19)	0.098 (2)	0.0513 (17)	−0.0100 (16)	0.0084 (14)	−0.0062 (16)
C7	0.0529 (16)	0.0653 (17)	0.0448 (16)	−0.0014 (13)	0.0080 (13)	0.0025 (12)
C8	0.0524 (15)	0.0516 (14)	0.0456 (15)	−0.0068 (12)	0.0121 (12)	−0.0030 (12)
C9	0.0502 (15)	0.0550 (16)	0.0516 (16)	−0.0112 (12)	0.0041 (12)	0.0032 (12)
C10	0.0705 (19)	0.0703 (17)	0.0454 (16)	−0.0090 (15)	0.0058 (13)	0.0030 (13)
C11	0.0694 (18)	0.0566 (16)	0.0486 (16)	−0.0128 (14)	0.0196 (13)	−0.0031 (12)
C12	0.0561 (17)	0.0836 (18)	0.0700 (18)	0.0001 (14)	0.0004 (13)	0.0025 (15)
C13	0.100 (2)	0.0828 (19)	0.0562 (17)	−0.0108 (17)	0.0289 (15)	−0.0094 (15)

O1—C7	1.292 (3)	C4—C5	1.365 (4)
O1—H1	0.820	C4—H4	0.930
O2—C7	1.218 (3)	C5—C6	1.399 (4)
N1—C9	1.336 (3)	C5—H5	0.930
N1—C8	1.350 (3)	C6—H6	0.930
N2—C11	1.326 (3)	C9—C10	1.385 (3)
N2—C8	1.364 (3)	C9—C12	1.494 (3)
N3—C8	1.322 (3)	C10—C11	1.376 (3)
N3—H3A	0.860	C10—H10	0.930
N3—H3B	0.860	C11—C13	1.507 (3)
C1—C6	1.372 (3)	C12—H12A	0.960
C1—C2	1.382 (3)	C12—H12B	0.960
C1—C7	1.489 (3)	C12—H12C	0.960
C2—C3	1.379 (4)	C13—H13A	0.960
C2—H2	0.930	C13—H13B	0.960
C3—C4	1.361 (4)	C13—H13C	0.960
C3—H3	0.930
C7—O1—H1	109.5	O1—C7—C1	114.2 (2)
C9—N1—C8	118.13 (19)	N3—C8—N1	118.5 (2)
C11—N2—C8	116.7 (2)	N3—C8—N2	117.4 (2)
C8—N3—H3A	120.0	N1—C8—N2	124.1 (2)
C8—N3—H3B	120.0	N1—C9—C10	120.4 (2)
H3A—N3—H3B	120.0	N1—C9—C12	116.9 (2)
C6—C1—C2	119.6 (2)	C10—C9—C12	122.7 (2)
C6—C1—C7	119.7 (2)	C11—C10—C9	118.4 (2)
C2—C1—C7	120.7 (2)	C11—C10—H10	120.8
C3—C2—C1	120.3 (3)	C9—C10—H10	120.8
C3—C2—H2	119.9	N2—C11—C10	122.3 (2)
C1—C2—H2	119.9	N2—C11—C13	116.1 (3)
C4—C3—C2	120.1 (3)	C10—C11—C13	121.6 (3)
C4—C3—H3	119.9	C9—C12—H12A	109.5
C2—C3—H3	119.9	C9—C12—H12B	109.5
C3—C4—C5	120.3 (3)	H12A—C12—H12B	109.5
C3—C4—H4	119.8	C9—C12—H12C	109.5
C5—C4—H4	119.8	H12A—C12—H12C	109.5
C4—C5—C6	120.2 (3)	H12B—C12—H12C	109.5
C4—C5—H5	119.9	C11—C13—H13A	109.5
C6—C5—H5	119.9	C11—C13—H13B	109.5
C1—C6—C5	119.4 (3)	H13A—C13—H13B	109.5
C1—C6—H6	120.3	C11—C13—H13C	109.5
C5—C6—H6	120.3	H13A—C13—H13C	109.5
O2—C7—O1	123.4 (2)	H13B—C13—H13C	109.5
O2—C7—C1	122.4 (2)
C6—C1—C2—C3	−2.1 (4)	C9—N1—C8—N3	−178.84 (19)
C7—C1—C2—C3	177.7 (2)	C9—N1—C8—N2	1.2 (3)
C1—C2—C3—C4	−0.3 (4)	C11—N2—C8—N3	178.20 (19)
C2—C3—C4—C5	1.8 (5)	C11—N2—C8—N1	−1.8 (3)
C3—C4—C5—C6	−0.9 (5)	C8—N1—C9—C10	−0.1 (3)
C2—C1—C6—C5	3.0 (4)	C8—N1—C9—C12	179.75 (19)
C7—C1—C6—C5	−176.8 (2)	N1—C9—C10—C11	−0.4 (3)
C4—C5—C6—C1	−1.5 (4)	C12—C9—C10—C11	179.9 (2)
C6—C1—C7—O2	−5.3 (4)	C8—N2—C11—C10	1.4 (3)
C2—C1—C7—O2	175.0 (2)	C8—N2—C11—C13	−178.11 (19)
C6—C1—C7—O1	174.4 (2)	C9—C10—C11—N2	−0.3 (4)
C2—C1—C7—O1	−5.3 (3)	C9—C10—C11—C13	179.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.82	2.606 (2)	160
N3—H3A···O2	0.86	2.16	3.003 (3)	168
N3—H3B···N2i	0.86	2.25	3.098 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.82	2.606 (2)	160
N3—H3A⋯O2	0.86	2.16	3.003 (3)	168
N3—H3B⋯N2i	0.86	2.25	3.098 (3)	169

Symmetry code: (i) .