Pyrimidin-2-amine-1-phenyl-cyclo-pentane-1-carb-oxy-lic acid (1/1).

In the crystal structure of the title co-crystal, C(4)H(5)N(3)·C(12)H(14)O(2), the components are linked by N-H⋯O and O-H⋯N hydrogen bonds. Self-assembly of these dimeric units results in a four-component supra-molecular unit featuring a homosynthon between two mol-ecules of the pyrimidin-2-amine involving two N-H⋯O hydrogen bonds, and two heterosynthons between each one mol-ecule of pyrimidin-2-amine and 1-phenyl-cyclo-pentane-1-carb-oxy-lic acid involving N-H⋯O and O-H⋯N hydrogen bonds.

Related literature

For the structure of pyrimidin-2-amine, see: Scheinbeim & Schempp (1976 ▶) and for the structure of 1-phenyl­cyclo­pentane-1-carb­oxy­lic acid, see: Margulis (1975 ▶). For mol­ecular co-crystals of pyrimidin-2-amine, see: Serafin & Wheeler (2007 ▶); Shan et al. (2002 ▶); Goswami et al. (1999a ▶,b ▶, 2000 ▶); Chinnakali et al. (1999 ▶); Lynch et al. (1997 ▶). For a salt of 2-amino­pyridine and 1-phenyl-1-cyclo­propane­carb­oxy­lic acid, see: He et al. (2010 ▶). For a recent screening study for co-crystal and salt formation using pulse-gradient spin–echo nuclear magnetic resonance, see: He et al. (2009 ▶).

Experimental

Crystal data

C4H5N3·C12H14O2

M = 285.34

Monoclinic,

a = 9.1461 (18) Å

b = 10.490 (2) Å

c = 15.474 (3) Å

β = 98.14 (3)°

V = 1469.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 110 K

0.44 × 0.44 × 0.22 mm

Data collection

Rigaku Saturn 70 CCD area-detector diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.963, T max = 0.981

20335 measured reflections

3641 independent reflections

3516 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.178

S = 1.21

3641 reflections

202 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003667/ng5101sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003667/ng5101Isup2.hkl

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

C4H5N3·C12H14O2	F(000) = 608
Mr = 285.34	Dx = 1.290 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.1461 (18) Å	Cell parameters from 4896 reflections
b = 10.490 (2) Å	θ = 1.9–31.1°
c = 15.474 (3) Å	µ = 0.09 mm−1
β = 98.14 (3)°	T = 110 K
V = 1469.7 (5) Å3	Block, colorless
Z = 4	0.44 × 0.44 × 0.22 mm

Rigaku Saturn 70 CCD area-detector diffractometer	3641 independent reflections
Radiation source: fine-focus sealed tube	3516 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (Blessing, 1995)	h = −12→12
Tmin = 0.963, Tmax = 0.981	k = −13→13
20335 measured reflections	l = −20→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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H atoms treated by a mixture of independent and constrained refinement
S = 1.21	w = 1/[σ2(Fo2) + (0.0804P)2 + 0.5855P] where P = (Fo2 + 2Fc2)/3
3641 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.28 e Å−3
1 restraint	Δρmin = −0.27 e Å−3

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
O2	0.04632 (14)	0.55094 (13)	0.70052 (8)	0.0344 (3)
O1	0.22224 (15)	0.40633 (14)	0.73866 (9)	0.0397 (3)
C16	0.12059 (18)	0.47154 (16)	0.75641 (11)	0.0281 (3)
C6	−0.09084 (18)	0.42117 (16)	0.83708 (10)	0.0273 (3)
C5	0.06701 (18)	0.47220 (17)	0.84621 (11)	0.0289 (4)
C8	−0.35533 (19)	0.45531 (18)	0.80273 (12)	0.0337 (4)
H8	−0.4356	0.5110	0.7842	0.040*
C12	0.17880 (19)	0.3999 (2)	0.91211 (12)	0.0396 (4)
H12A	0.2180	0.3247	0.8843	0.047*
H12B	0.1319	0.3709	0.9625	0.047*
C7	−0.21065 (18)	0.50062 (17)	0.81043 (11)	0.0305 (4)
H7	−0.1936	0.5873	0.7972	0.037*
C10	−0.2643 (2)	0.24866 (18)	0.84809 (12)	0.0362 (4)
H10	−0.2821	0.1620	0.8610	0.043*
C11	−0.1195 (2)	0.29396 (17)	0.85543 (12)	0.0332 (4)
H11	−0.0395	0.2376	0.8731	0.040*
C15	0.0807 (2)	0.6105 (2)	0.88196 (13)	0.0380 (4)
H15A	0.0410	0.6727	0.8365	0.046*
H15B	0.0279	0.6204	0.9332	0.046*
C9	−0.3820 (2)	0.32934 (19)	0.82208 (12)	0.0354 (4)
H9	−0.4805	0.2985	0.8175	0.042*
C13	0.3039 (2)	0.4964 (3)	0.94177 (14)	0.0523 (6)
H13A	0.3269	0.4975	1.0062	0.063*
H13B	0.3945	0.4731	0.9172	0.063*
C14	0.2473 (2)	0.6273 (2)	0.90771 (16)	0.0517 (6)
H14A	0.2684	0.6930	0.9537	0.062*
H14B	0.2944	0.6530	0.8566	0.062*
H6	0.082 (3)	0.557 (3)	0.6516 (13)	0.066 (8)*
C2	0.24306 (19)	0.66091 (17)	0.39920 (12)	0.0318 (4)
H2	0.2760	0.6860	0.3462	0.038*
N3	0.36606 (18)	0.47957 (17)	0.58582 (11)	0.0391 (4)
N1	0.14713 (15)	0.58831 (14)	0.54997 (9)	0.0299 (3)
N2	0.33123 (16)	0.58740 (14)	0.45437 (10)	0.0314 (3)
C3	0.1056 (2)	0.70251 (18)	0.41554 (12)	0.0345 (4)
H3	0.0445	0.7554	0.3757	0.041*
C4	0.06304 (19)	0.66250 (18)	0.49318 (12)	0.0346 (4)
H4	−0.0304	0.6890	0.5068	0.041*
H5	0.331 (3)	0.447 (2)	0.6325 (17)	0.051 (7)*
C1	0.27973 (18)	0.55295 (16)	0.52886 (11)	0.0285 (3)
H1	0.451 (3)	0.454 (2)	0.5716 (16)	0.051 (7)*

	U11	U22	U33	U12	U13	U23
O2	0.0317 (6)	0.0434 (7)	0.0300 (6)	0.0106 (5)	0.0113 (5)	0.0085 (5)
O1	0.0385 (7)	0.0472 (8)	0.0361 (7)	0.0150 (6)	0.0146 (6)	0.0093 (6)
C16	0.0247 (7)	0.0303 (8)	0.0297 (8)	−0.0005 (6)	0.0056 (6)	0.0009 (6)
C6	0.0259 (7)	0.0322 (8)	0.0249 (8)	−0.0013 (6)	0.0071 (6)	−0.0011 (6)
C5	0.0226 (7)	0.0380 (9)	0.0268 (8)	−0.0023 (6)	0.0055 (6)	−0.0003 (6)
C8	0.0249 (8)	0.0410 (9)	0.0361 (9)	0.0003 (7)	0.0070 (7)	−0.0050 (7)
C12	0.0264 (8)	0.0626 (13)	0.0297 (9)	0.0001 (8)	0.0039 (7)	0.0093 (8)
C7	0.0279 (8)	0.0307 (8)	0.0336 (9)	−0.0016 (6)	0.0074 (6)	−0.0031 (7)
C10	0.0408 (10)	0.0329 (9)	0.0364 (9)	−0.0097 (7)	0.0102 (7)	−0.0021 (7)
C11	0.0331 (9)	0.0333 (9)	0.0336 (9)	0.0005 (7)	0.0058 (7)	0.0018 (7)
C15	0.0305 (9)	0.0449 (10)	0.0402 (10)	−0.0110 (7)	0.0106 (7)	−0.0113 (8)
C9	0.0303 (8)	0.0436 (10)	0.0339 (9)	−0.0108 (7)	0.0104 (7)	−0.0084 (7)
C13	0.0274 (9)	0.0954 (18)	0.0335 (10)	−0.0092 (10)	0.0018 (8)	−0.0042 (11)
C14	0.0357 (10)	0.0700 (15)	0.0500 (12)	−0.0211 (10)	0.0082 (9)	−0.0156 (11)
C2	0.0328 (8)	0.0344 (9)	0.0292 (8)	0.0018 (7)	0.0077 (6)	0.0018 (7)
N3	0.0306 (8)	0.0513 (10)	0.0383 (9)	0.0149 (7)	0.0150 (7)	0.0168 (7)
N1	0.0238 (6)	0.0371 (8)	0.0294 (7)	0.0027 (5)	0.0065 (5)	0.0024 (6)
N2	0.0294 (7)	0.0340 (7)	0.0320 (8)	0.0035 (6)	0.0087 (6)	0.0040 (6)
C3	0.0304 (8)	0.0403 (10)	0.0326 (9)	0.0052 (7)	0.0045 (7)	0.0057 (7)
C4	0.0257 (8)	0.0437 (10)	0.0348 (9)	0.0070 (7)	0.0060 (6)	0.0041 (7)
C1	0.0256 (8)	0.0291 (8)	0.0316 (8)	0.0016 (6)	0.0066 (6)	0.0010 (6)

O2—C16	1.318 (2)	C15—H15A	0.9900
O2—H6	0.869 (17)	C15—H15B	0.9900
O1—C16	1.217 (2)	C9—H9	0.9500
C16—C5	1.537 (2)	C13—C14	1.535 (4)
C6—C7	1.392 (2)	C13—H13A	0.9900
C6—C11	1.397 (2)	C13—H13B	0.9900
C6—C5	1.527 (2)	C14—H14A	0.9900
C5—C12	1.538 (2)	C14—H14B	0.9900
C5—C15	1.551 (3)	C2—N2	1.334 (2)
C8—C9	1.384 (3)	C2—C3	1.387 (2)
C8—C7	1.395 (2)	C2—H2	0.9500
C8—H8	0.9500	N3—C1	1.340 (2)
C12—C13	1.548 (3)	N3—H5	0.90 (3)
C12—H12A	0.9900	N3—H1	0.88 (3)
C12—H12B	0.9900	N1—C4	1.334 (2)
C7—H7	0.9500	N1—C1	1.352 (2)
C10—C9	1.384 (3)	N2—C1	1.355 (2)
C10—C11	1.397 (2)	C3—C4	1.380 (3)
C10—H10	0.9500	C3—H3	0.9500
C11—H11	0.9500	C4—H4	0.9500
C15—C14	1.530 (3)
C16—O2—H6	113.4 (19)	C5—C15—H15B	111.1
O1—C16—O2	123.13 (16)	H15A—C15—H15B	109.1
O1—C16—C5	123.93 (16)	C10—C9—C8	119.54 (16)
O2—C16—C5	112.93 (14)	C10—C9—H9	120.2
C7—C6—C11	118.03 (15)	C8—C9—H9	120.2
C7—C6—C5	120.77 (15)	C14—C13—C12	106.50 (16)
C11—C6—C5	121.20 (15)	C14—C13—H13A	110.4
C6—C5—C16	109.44 (13)	C12—C13—H13A	110.4
C6—C5—C12	114.81 (15)	C14—C13—H13B	110.4
C16—C5—C12	109.27 (14)	C12—C13—H13B	110.4
C6—C5—C15	112.84 (14)	H13A—C13—H13B	108.6
C16—C5—C15	107.86 (14)	C15—C14—C13	105.13 (18)
C12—C5—C15	102.24 (15)	C15—C14—H14A	110.7
C9—C8—C7	120.06 (17)	C13—C14—H14A	110.7
C9—C8—H8	120.0	C15—C14—H14B	110.7
C7—C8—H8	120.0	C13—C14—H14B	110.7
C5—C12—C13	105.58 (17)	H14A—C14—H14B	108.8
C5—C12—H12A	110.6	N2—C2—C3	123.13 (16)
C13—C12—H12A	110.6	N2—C2—H2	118.4
C5—C12—H12B	110.6	C3—C2—H2	118.4
C13—C12—H12B	110.6	C1—N3—H5	120.2 (16)
H12A—C12—H12B	108.8	C1—N3—H1	118.2 (16)
C6—C7—C8	121.24 (16)	H5—N3—H1	121 (2)
C6—C7—H7	119.4	C4—N1—C1	117.03 (15)
C8—C7—H7	119.4	C2—N2—C1	116.58 (15)
C9—C10—C11	120.36 (17)	C4—C3—C2	115.97 (16)
C9—C10—H10	119.8	C4—C3—H3	122.0
C11—C10—H10	119.8	C2—C3—H3	122.0
C10—C11—C6	120.76 (17)	N1—C4—C3	122.94 (16)
C10—C11—H11	119.6	N1—C4—H4	118.5
C6—C11—H11	119.6	C3—C4—H4	118.5
C14—C15—C5	103.19 (17)	N3—C1—N1	117.64 (16)
C14—C15—H15A	111.1	N3—C1—N2	118.00 (15)
C5—C15—H15A	111.1	N1—C1—N2	124.36 (16)
C14—C15—H15B	111.1

D—H···A	D—H	H···A	D···A	D—H···A
O2—H6···N1	0.87 (2)	1.79 (2)	2.653 (2)	173 (3)
N3—H5···O1	0.90 (3)	2.08 (3)	2.966 (2)	168 (2)
N3—H1···N2i	0.88 (3)	2.13 (3)	3.006 (2)	173 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H6⋯N1	0.87 (2)	1.79 (2)	2.653 (2)	173 (3)
N3—H5⋯O1	0.90 (3)	2.08 (3)	2.966 (2)	168 (2)
N3—H1⋯N2i	0.88 (3)	2.13 (3)	3.006 (2)	173 (2)

Symmetry code: (i) .