2-Chloro-5-fluoro-6-methyl-N-o-tolyl-pyrimidin-4-amine.

In the title compound, C12H11ClFN3, the benzene ring forms a dihedral angle of 72.43 (5)° with the pyrimidine ring. In the crystal, N-H⋯N hydrogen bonds link the mol-ecules into a chain running along the c axis.

Related literature

For background to and applications of fluoro-pyrimidines, see: Riccaboni et al. (2010 ▶). For the anti­tumor activity of 4-aniline-substituted 5-fluoro­pyrimidines, see: Lawrence et al. (2012 ▶).

Experimental

Crystal data

C12H11ClFN3

M = 251.69

Monoclinic,

a = 12.0593 (7) Å

b = 8.3684 (4) Å

c = 12.8611 (6) Å

β = 113.021 (6)°

V = 1194.54 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 293 K

0.5 × 0.3 × 0.2 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

4692 measured reflections

2125 independent reflections

1750 reflections with I > 2σ(I)

R int = 0.014

3 standard reflections every 60 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.096

S = 1.04

2125 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 Software (Enraf–Nonius, 1994 ▶); data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681300812X/is5256sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300812X/is5256Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681300812X/is5256Isup3.cml

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

C12H11ClFN3	F(000) = 520
Mr = 251.69	Dx = 1.399 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1870 reflections
a = 12.0593 (7) Å	θ = 3.0–29.1°
b = 8.3684 (4) Å	µ = 0.31 mm−1
c = 12.8611 (6) Å	T = 293 K
β = 113.021 (6)°	Prismatic, colourless
V = 1194.54 (11) Å3	0.5 × 0.3 × 0.2 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.014
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 3.0°
Graphite monochromator	h = −7→14
phi and ω scans	k = −9→9
4692 measured reflections	l = −15→15
2125 independent reflections	3 standard reflections every 60 min
1750 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0466P)2 + 0.2577P] where P = (Fo2 + 2Fc2)/3
2125 reflections	(Δ/σ)max = 0.002
156 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.21 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
Cl1	0.75856 (5)	−0.06428 (7)	1.24493 (4)	0.0666 (2)
N2	0.57335 (12)	0.12020 (18)	1.15433 (11)	0.0470 (4)
N3	0.70666 (11)	0.09036 (16)	1.05829 (11)	0.0407 (3)
F1	0.46632 (9)	0.35255 (15)	0.89928 (9)	0.0694 (3)
C1	0.66841 (15)	0.0648 (2)	1.14005 (14)	0.0426 (4)
C4	0.63837 (14)	0.1897 (2)	0.97700 (13)	0.0401 (4)
C3	0.53397 (14)	0.2537 (2)	0.98347 (14)	0.0448 (4)
N1	0.66996 (12)	0.22514 (18)	0.89014 (11)	0.0484 (4)
H1	0.6236	0.2882	0.8387	0.058*
C2	0.50232 (14)	0.2189 (2)	1.07122 (15)	0.0460 (4)
C6	0.77521 (15)	0.1655 (2)	0.87727 (13)	0.0445 (4)
C11	0.7589 (2)	0.0547 (2)	0.79274 (17)	0.0627 (5)
H11	0.6821	0.0171	0.7491	0.075*
C5	0.39149 (18)	0.2840 (3)	1.08108 (19)	0.0684 (6)
H5A	0.3501	0.3528	1.0180	0.103*
H5B	0.4136	0.3437	1.1500	0.103*
H5C	0.3395	0.1974	1.0816	0.103*
C10	0.8577 (3)	0.0005 (3)	0.7736 (2)	0.0862 (8)
H10	0.8482	−0.0745	0.7174	0.103*
C8	0.98515 (19)	0.1680 (4)	0.9222 (2)	0.0824 (8)
H8	1.0622	0.2052	0.9653	0.099*
C9	0.9696 (3)	0.0584 (4)	0.8384 (3)	0.0925 (9)
H9	1.0361	0.0229	0.8254	0.111*
C7	0.88790 (16)	0.2248 (2)	0.94391 (16)	0.0560 (5)
C12	0.9052 (2)	0.3424 (3)	1.03578 (19)	0.0804 (7)
H12A	0.8506	0.4302	1.0065	0.121*
H12B	0.9866	0.3812	1.0645	0.121*
H12C	0.8896	0.2916	1.0956	0.121*

	U11	U22	U33	U12	U13	U23
Cl1	0.0636 (3)	0.0849 (4)	0.0599 (3)	0.0128 (3)	0.0333 (3)	0.0278 (3)
N2	0.0441 (8)	0.0583 (9)	0.0462 (8)	−0.0052 (7)	0.0260 (7)	−0.0057 (7)
N3	0.0368 (7)	0.0512 (8)	0.0382 (7)	−0.0006 (6)	0.0192 (6)	0.0011 (6)
F1	0.0534 (6)	0.0882 (8)	0.0641 (7)	0.0227 (6)	0.0204 (5)	0.0185 (6)
C1	0.0413 (9)	0.0500 (10)	0.0411 (9)	−0.0061 (8)	0.0213 (7)	−0.0017 (7)
C4	0.0362 (8)	0.0502 (10)	0.0348 (8)	−0.0044 (7)	0.0150 (7)	−0.0043 (7)
C3	0.0371 (9)	0.0516 (10)	0.0426 (9)	0.0027 (8)	0.0122 (7)	−0.0005 (8)
N1	0.0428 (8)	0.0680 (10)	0.0374 (7)	0.0082 (7)	0.0188 (6)	0.0104 (7)
C2	0.0382 (9)	0.0524 (10)	0.0514 (10)	−0.0051 (8)	0.0221 (8)	−0.0125 (8)
C6	0.0463 (9)	0.0549 (10)	0.0391 (8)	0.0032 (8)	0.0240 (7)	0.0082 (8)
C11	0.0787 (14)	0.0675 (13)	0.0503 (11)	−0.0011 (11)	0.0344 (10)	0.0004 (9)
C5	0.0537 (11)	0.0799 (14)	0.0853 (15)	0.0077 (10)	0.0419 (11)	−0.0074 (12)
C10	0.133 (2)	0.0771 (16)	0.0817 (16)	0.0254 (17)	0.0782 (18)	0.0111 (13)
C8	0.0516 (12)	0.118 (2)	0.0884 (16)	0.0097 (13)	0.0386 (12)	0.0359 (16)
C9	0.095 (2)	0.110 (2)	0.109 (2)	0.0400 (17)	0.0793 (18)	0.0411 (18)
C7	0.0487 (10)	0.0710 (13)	0.0524 (10)	−0.0027 (9)	0.0240 (9)	0.0115 (9)
C12	0.0692 (14)	0.0959 (17)	0.0673 (14)	−0.0293 (13)	0.0171 (11)	−0.0094 (13)

Cl1—C1	1.7384 (17)	C11—H11	0.9300
N2—C1	1.314 (2)	C5—H5A	0.9600
N2—C2	1.357 (2)	C5—H5B	0.9600
N3—C1	1.321 (2)	C5—H5C	0.9600
N3—C4	1.337 (2)	C10—C9	1.367 (4)
F1—C3	1.3533 (19)	C10—H10	0.9300
C4—N1	1.347 (2)	C8—C9	1.371 (4)
C4—C3	1.400 (2)	C8—C7	1.391 (3)
C3—C2	1.357 (2)	C8—H8	0.9300
N1—C6	1.433 (2)	C9—H9	0.9300
N1—H1	0.8600	C7—C12	1.488 (3)
C2—C5	1.494 (2)	C12—H12A	0.9600
C6—C11	1.383 (3)	C12—H12B	0.9600
C6—C7	1.385 (2)	C12—H12C	0.9600
C11—C10	1.384 (3)
C1—N2—C2	114.88 (14)	C2—C5—H5B	109.5
C1—N3—C4	115.01 (14)	H5A—C5—H5B	109.5
N2—C1—N3	130.53 (16)	C2—C5—H5C	109.5
N2—C1—Cl1	115.19 (12)	H5A—C5—H5C	109.5
N3—C1—Cl1	114.28 (12)	H5B—C5—H5C	109.5
N3—C4—N1	119.86 (14)	C9—C10—C11	119.3 (2)
N3—C4—C3	118.98 (14)	C9—C10—H10	120.4
N1—C4—C3	121.15 (15)	C11—C10—H10	120.4
F1—C3—C2	121.27 (15)	C9—C8—C7	121.3 (2)
F1—C3—C4	117.46 (14)	C9—C8—H8	119.3
C2—C3—C4	121.27 (16)	C7—C8—H8	119.3
C4—N1—C6	124.73 (14)	C10—C9—C8	121.0 (2)
C4—N1—H1	117.6	C10—C9—H9	119.5
C6—N1—H1	117.6	C8—C9—H9	119.5
N2—C2—C3	119.31 (15)	C6—C7—C8	117.0 (2)
N2—C2—C5	117.72 (16)	C6—C7—C12	121.83 (17)
C3—C2—C5	122.97 (17)	C8—C7—C12	121.2 (2)
C11—C6—C7	122.05 (17)	C7—C12—H12A	109.5
C11—C6—N1	117.67 (16)	C7—C12—H12B	109.5
C7—C6—N1	120.19 (16)	H12A—C12—H12B	109.5
C6—C11—C10	119.4 (2)	C7—C12—H12C	109.5
C6—C11—H11	120.3	H12A—C12—H12C	109.5
C10—C11—H11	120.3	H12B—C12—H12C	109.5
C2—C5—H5A	109.5
C2—N2—C1—N3	0.5 (3)	F1—C3—C2—C5	0.8 (3)
C2—N2—C1—Cl1	−178.98 (11)	C4—C3—C2—C5	−179.72 (17)
C4—N3—C1—N2	0.6 (3)	C4—N1—C6—C11	109.29 (19)
C4—N3—C1—Cl1	−179.90 (11)	C4—N1—C6—C7	−74.2 (2)
C1—N3—C4—N1	179.34 (15)	C7—C6—C11—C10	0.2 (3)
C1—N3—C4—C3	−1.3 (2)	N1—C6—C11—C10	176.61 (17)
N3—C4—C3—F1	−179.39 (14)	C6—C11—C10—C9	−0.5 (3)
N1—C4—C3—F1	−0.1 (2)	C11—C10—C9—C8	0.6 (4)
N3—C4—C3—C2	1.1 (2)	C7—C8—C9—C10	−0.4 (4)
N1—C4—C3—C2	−179.61 (16)	C11—C6—C7—C8	0.0 (3)
N3—C4—N1—C6	−0.9 (3)	N1—C6—C7—C8	−176.33 (16)
C3—C4—N1—C6	179.75 (16)	C11—C6—C7—C12	−179.19 (18)
C1—N2—C2—C3	−0.8 (2)	N1—C6—C7—C12	4.5 (3)
C1—N2—C2—C5	178.99 (16)	C9—C8—C7—C6	0.1 (3)
F1—C3—C2—N2	−179.44 (14)	C9—C8—C7—C12	179.3 (2)
C4—C3—C2—N2	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.86	2.34	3.0768 (19)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.86	2.34	3.0768 (19)	145

Symmetry code: (i) .