2-Amino-6-chloro-4-(1-phenyl­ethyl­amino)­pyrimidine

The structure of the title compound, C₁₂H₁₃ClN₄, (I), comprises a racemic mixture of chiral mol­ecules associated by N-H...N hydrogen-bonding interactions. The dihedral angle between the two rings is 77.90 (6)°.

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

2-Amino-6-chloro-4-(1-phenylethylamino)pyrimidine

Crystal data

C12H13ClN4	Dx = 1.327 Mg m^−3
Mr = 248.71	Melting point: 414-416 K K
Tetragonal, I41/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 4ad	Cell parameters from 10256 reflections
a = 17.4851 (7) Å	θ = 2.9–27.5°
c = 16.2878 (9) Å	µ = 0.29 mm^−1
V = 4979.6 (4) Å^3	T = 150 K
Z = 16	Block, yellow
F(000) = 2080	0.15 × 0.10 × 0.10 mm

Data collection

Enraf Nonius KappaCCD area-detector diffractometer	2828 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1893 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.137
Detector resolution: 9.091 pixels mm^-1	θmax = 27.4°, θmin = 3.0°
φ and ω scans	h = −22→22
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −19→19
Tmin = 0.958, Tmax = 0.972	l = −17→21
15828 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.134	w = 1/[σ^2(Fo^2) + (0.0658P)^2 + 0.1078P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
2828 reflections	Δρmax = 0.24 e Å^−3
156 parameters	Δρmin = −0.35 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (3)

Special details

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Geometry. Mean plane data ex SHELXL97 ###########################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 5.1343 (0.0120) x + 14.0482 (0.0084) y + 8.4361 (0.0108) z = 4.5614 (0.0063)

* -0.0070 (0.0012) N1 * -0.0139 (0.0013) C2 * 0.0246 (0.0012) N3 * -0.0159 (0.0013) C4 * -0.0042 (0.0013) C5 * 0.0165 (0.0013) C6 0.0240 (0.0024) Cl6 - 0.0933 (0.0028) N21 - 0.0672 (0.0027) N41

Rms deviation of fitted atoms = 0.0152

17.3791 (0.0019) x + 0.6172 (0.0152) y + 1.6959 (0.0144) z = 10.6236 (0.0055)

Angle to previous plane (with approximate e.s.d.) = 77.90 (0.06)

* 0.0047 (0.0014) C44 * -0.0018 (0.0015) C45 * -0.0020 (0.0015) C46 * 0.0029 (0.0015) C47 * 0.0001 (0.0016) C48 * -0.0039 (0.0016) C49 0.0730 (0.0033) C42

Rms deviation of fitted atoms = 0.0029

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.31739 (9)	0.31705 (9)	0.20507 (10)	0.0320 (4)
C2	0.36717 (11)	0.29808 (11)	0.26613 (12)	0.0303 (5)
N21	0.34152 (10)	0.24900 (10)	0.32285 (10)	0.0401 (5)
H21	0.3718	0.2342	0.3630	0.050*
H22	0.2944	0.2315	0.3200	0.050*
N3	0.43912 (9)	0.32257 (9)	0.27372 (9)	0.0306 (4)
C4	0.46688 (11)	0.36657 (10)	0.21254 (12)	0.0301 (5)
C5	0.42008 (11)	0.38992 (11)	0.14655 (12)	0.0310 (5)
H5	0.4383	0.4219	0.1036	0.039*
C6	0.34694 (11)	0.36324 (11)	0.14893 (12)	0.0306 (5)
Cl6	0.28398 (3)	0.38817 (3)	0.06998 (3)	0.0423 (2)
N41	0.54094 (9)	0.38579 (9)	0.21952 (10)	0.0350 (4)
H41	0.5654	0.3692	0.2632	0.044*
C42	0.58444 (12)	0.43178 (11)	0.16105 (13)	0.0355 (5)
H42	0.5584	0.4824	0.1551	0.044*
C43	0.66346 (13)	0.44519 (14)	0.19751 (15)	0.0485 (6)
H431	0.6584	0.4704	0.2509	0.061*
H432	0.6933	0.4777	0.1605	0.061*
H433	0.6896	0.3960	0.2046	0.061*
C44	0.59000 (10)	0.39531 (11)	0.07702 (12)	0.0319 (5)
C45	0.59478 (12)	0.44099 (12)	0.00766 (13)	0.0393 (5)
H45	0.5921	0.4950	0.0131	0.049*
C46	0.60340 (13)	0.40891 (13)	−0.06919 (13)	0.0442 (6)
H46	0.6066	0.4410	−0.1161	0.055*
C47	0.60735 (12)	0.33102 (13)	−0.07838 (14)	0.0416 (6)
H47	0.6136	0.3090	−0.1313	0.052*
C48	0.60210 (13)	0.28490 (13)	−0.00951 (14)	0.0483 (6)
H48	0.6046	0.2309	−0.0152	0.060*
C49	0.59323 (13)	0.31706 (12)	0.06741 (14)	0.0442 (6)
H49	0.5893	0.2849	0.1142	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0349 (9)	0.0330 (9)	0.0281 (9)	0.0007 (7)	−0.0003 (7)	0.0028 (7)
C2	0.0375 (12)	0.0285 (11)	0.0249 (10)	0.0017 (8)	−0.0008 (8)	−0.0004 (8)
N21	0.0404 (11)	0.0489 (11)	0.0310 (10)	−0.0110 (8)	−0.0057 (8)	0.0131 (8)
N3	0.0362 (10)	0.0298 (9)	0.0257 (9)	−0.0002 (7)	−0.0016 (7)	0.0008 (7)
C4	0.0352 (11)	0.0263 (10)	0.0287 (10)	0.0002 (8)	−0.0003 (8)	−0.0037 (8)
C5	0.0363 (11)	0.0280 (10)	0.0288 (11)	−0.0014 (8)	−0.0005 (9)	0.0050 (8)
C6	0.0374 (11)	0.0261 (10)	0.0282 (10)	0.0032 (8)	−0.0038 (8)	0.0012 (8)
Cl6	0.0395 (3)	0.0475 (4)	0.0399 (4)	0.0003 (2)	−0.0080 (2)	0.0143 (2)
N41	0.0362 (10)	0.0372 (10)	0.0315 (10)	−0.0049 (7)	−0.0046 (7)	0.0037 (7)
C42	0.0382 (12)	0.0302 (11)	0.0382 (12)	−0.0047 (8)	0.0000 (9)	0.0032 (9)
C43	0.0432 (13)	0.0530 (15)	0.0494 (15)	−0.0159 (11)	−0.0046 (11)	−0.0010 (12)
C44	0.0253 (10)	0.0321 (11)	0.0383 (12)	−0.0015 (8)	−0.0025 (8)	0.0017 (9)
C45	0.0439 (13)	0.0306 (11)	0.0435 (13)	−0.0010 (9)	0.0036 (10)	0.0066 (10)
C46	0.0498 (14)	0.0462 (14)	0.0366 (13)	0.0035 (10)	0.0014 (10)	0.0094 (10)
C47	0.0401 (12)	0.0496 (14)	0.0350 (12)	0.0059 (10)	−0.0011 (10)	−0.0022 (10)
C48	0.0622 (16)	0.0364 (13)	0.0463 (15)	0.0080 (10)	−0.0023 (12)	−0.0011 (11)
C49	0.0613 (15)	0.0327 (12)	0.0387 (13)	0.0027 (10)	−0.0002 (11)	0.0064 (10)

Geometric parameters (Å, º)

N1—C6	1.325 (2)	C42—H42	1.0000
N1—C2	1.363 (2)	C43—H431	0.9800
C2—N3	1.335 (3)	C43—H432	0.9800
C2—N21	1.338 (2)	C43—H433	0.9800
N21—H21	0.8800	C44—C49	1.378 (3)
N21—H22	0.8800	C44—C45	1.386 (3)
N3—C4	1.349 (2)	C45—C46	1.380 (3)
C4—N41	1.343 (3)	C45—H45	0.9500
C4—C5	1.411 (3)	C46—C47	1.372 (3)
C5—C6	1.362 (3)	C46—H46	0.9500
C5—H5	0.9500	C47—C48	1.384 (3)
C6—Cl6	1.7481 (19)	C47—H47	0.9500
N41—C42	1.460 (2)	C48—C49	1.382 (3)
N41—H41	0.8800	C48—H48	0.9500
C42—C44	1.513 (3)	C49—H49	0.9500
C42—C43	1.522 (3)
C6—N1—C2	113.77 (17)	C43—C42—H42	108.3
N3—C2—N21	117.23 (17)	C42—C43—H431	109.5
N3—C2—N1	126.27 (18)	C42—C43—H432	109.5
N21—C2—N1	116.48 (18)	H431—C43—H432	109.5
C2—N21—H21	120.0	C42—C43—H433	109.5
C2—N21—H22	120.0	H431—C43—H433	109.5
H21—N21—H22	120.0	H432—C43—H433	109.5
C2—N3—C4	116.97 (16)	C49—C44—C45	118.49 (19)
N41—C4—N3	115.28 (18)	C49—C44—C42	121.58 (18)
N41—C4—C5	123.46 (18)	C45—C44—C42	119.89 (18)
N3—C4—C5	121.26 (18)	C46—C45—C44	120.8 (2)
C6—C5—C4	115.07 (18)	C46—C45—H45	119.6
C6—C5—H5	122.5	C44—C45—H45	119.6
C4—C5—H5	122.5	C47—C46—C45	120.5 (2)
N1—C6—C5	126.50 (18)	C47—C46—H46	119.7
N1—C6—Cl6	114.46 (14)	C45—C46—H46	119.7
C5—C6—Cl6	119.01 (15)	C46—C47—C48	119.1 (2)
C4—N41—C42	125.80 (17)	C46—C47—H47	120.4
C4—N41—H41	117.1	C48—C47—H47	120.4
C42—N41—H41	117.1	C49—C48—C47	120.3 (2)
N41—C42—C44	113.04 (15)	C49—C48—H48	119.8
N41—C42—C43	107.66 (17)	C47—C48—H48	119.8
C44—C42—C43	111.07 (18)	C44—C49—C48	120.8 (2)
N41—C42—H42	108.3	C44—C49—H49	119.6
C44—C42—H42	108.3	C48—C49—H49	119.6
C6—N1—C2—N3	1.3 (3)	C4—N41—C42—C44	−62.1 (3)
C6—N1—C2—N21	−177.33 (17)	C4—N41—C42—C43	174.84 (19)
N21—C2—N3—C4	174.25 (17)	N41—C42—C44—C49	−33.2 (3)
N1—C2—N3—C4	−4.4 (3)	C43—C42—C44—C49	88.0 (2)
C2—N3—C4—N41	−175.65 (16)	N41—C42—C44—C45	149.19 (18)
C2—N3—C4—C5	4.3 (3)	C43—C42—C44—C45	−89.7 (2)
N41—C4—C5—C6	178.43 (18)	C49—C44—C45—C46	−0.7 (3)
N3—C4—C5—C6	−1.6 (3)	C42—C44—C45—C46	177.02 (19)
C2—N1—C6—C5	2.0 (3)	C44—C45—C46—C47	0.1 (3)
C2—N1—C6—Cl6	179.94 (13)	C45—C46—C47—C48	0.4 (3)
C4—C5—C6—N1	−1.8 (3)	C46—C47—C48—C49	−0.2 (3)
C4—C5—C6—Cl6	−179.68 (14)	C45—C44—C49—C48	0.9 (3)
N3—C4—N41—C42	179.04 (17)	C42—C44—C49—C48	−176.8 (2)
C5—C4—N41—C42	−1.0 (3)	C47—C48—C49—C44	−0.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···N3^i	0.88	2.23	3.098 (2)	169
N21—H22···N1^ii	0.88	2.17	3.043 (2)	172

Symmetry codes: (i) −y+3/4, x−1/4, −z+3/4; (ii) −x+1/2, −y+1/2, −z+1/2.