6-Chloro-N-methyl-5-nitro-N-phenyl-pyrimidin-4-amine.

In the title compound, C(11)H(9)ClN(4)O(2), the dihedral angle between the aromatic rings is 79.67 (8)°. π-π stacking between centrosymmetrically related pairs of pyrimidine rings occurs along [100] [centroid-centroid separations = 3.4572 (8) and 3.5433 (7) Å].

Related literature

For a related structure, see: Shi et al. (2011 ▶).

Experimental

Crystal data

C11H9ClN4O2

M = 264.67

Triclinic,

a = 6.8980 (14) Å

b = 8.9282 (18) Å

c = 11.427 (2) Å

α = 73.76 (3)°

β = 86.80 (3)°

γ = 84.21 (3)°

V = 672.0 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.44 × 0.38 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.885, T max = 0.964

5925 measured reflections

2730 independent reflections

1742 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.154

S = 1.07

2730 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.19 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2000 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811037664/ng5229sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037664/ng5229Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037664/ng5229Isup3.cml

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

C11H9ClN4O2	Z = 2
Mr = 264.67	F(000) = 272
Triclinic, P1	Dx = 1.308 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8980 (14) Å	Cell parameters from 500 reflections
b = 8.9282 (18) Å	θ = 3.4–27.5°
c = 11.427 (2) Å	µ = 0.28 mm−1
α = 73.76 (3)°	T = 293 K
β = 86.80 (3)°	Block, colorless
γ = 84.21 (3)°	0.44 × 0.38 × 0.13 mm
V = 672.0 (2) Å3

Rigaku R-AXIS RAPID diffractometer	2730 independent reflections
Radiation source: fine-focus sealed tube	1742 reflections with I > 2σ(I)
graphite	Rint = 0.030
Detector resolution: 10.00 pixels mm-1	θmax = 27.5°, θmin = 3.4°
ω scans	h = −8→7
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −10→10
Tmin = 0.885, Tmax = 0.964	l = −14→14
5925 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0827P)2 + 0.0097P] where P = (Fo2 + 2Fc2)/3
2730 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.19 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	0.27001 (12)	0.38397 (9)	0.55435 (6)	0.0897 (3)
C1	0.2612 (3)	0.1851 (3)	0.52481 (19)	0.0585 (5)
C2	0.2496 (3)	0.1772 (2)	0.40780 (17)	0.0483 (5)
C3	0.2386 (3)	0.0133 (2)	0.38625 (17)	0.0485 (5)
C4	0.2470 (3)	−0.1014 (3)	0.59315 (19)	0.0655 (6)
H4	0.2468	−0.1895	0.6599	0.079*
N1	0.2346 (3)	−0.1270 (2)	0.48527 (16)	0.0600 (5)
N2	0.2610 (3)	0.0465 (3)	0.62119 (16)	0.0694 (6)
C5	0.2510 (3)	0.1072 (2)	0.16239 (18)	0.0544 (5)
C6	0.4329 (4)	0.1522 (3)	0.1186 (2)	0.0716 (7)
H6	0.5428	0.1063	0.1631	0.086*
C7	0.4528 (5)	0.2692 (4)	0.0051 (3)	0.0954 (9)
H7	0.5759	0.3000	−0.0227	0.114*
C8	0.2935 (6)	0.3371 (4)	−0.0638 (2)	0.1037 (11)
H8	0.3077	0.4122	−0.1381	0.124*
C9	0.1135 (6)	0.2917 (4)	−0.0205 (3)	0.1034 (11)
H9	0.0043	0.3376	−0.0656	0.124*
C10	0.0897 (4)	0.1749 (3)	0.0930 (2)	0.0817 (8)
H10	−0.0337	0.1445	0.1202	0.098*
C11	0.2102 (5)	−0.1969 (3)	0.2719 (3)	0.0965 (10)
H11A	0.3338	−0.2570	0.2895	0.145*
H11B	0.1728	−0.1948	0.1917	0.145*
H11C	0.1136	−0.2440	0.3307	0.145*
N4	0.2395 (3)	0.3422 (2)	0.31108 (16)	0.0611 (5)
N3	0.2279 (3)	−0.0184 (2)	0.27815 (15)	0.0610 (5)
O1	0.0799 (3)	0.4051 (2)	0.27365 (17)	0.0885 (6)
O2	0.3903 (3)	0.4091 (2)	0.27659 (17)	0.0889 (6)

	U11	U22	U33	U12	U13	U23
Cl1	0.1161 (6)	0.1002 (6)	0.0686 (4)	−0.0261 (4)	0.0009 (4)	−0.0440 (4)
C1	0.0513 (12)	0.0778 (15)	0.0475 (11)	−0.0073 (9)	−0.0013 (9)	−0.0187 (10)
C2	0.0444 (10)	0.0555 (12)	0.0418 (10)	−0.0054 (8)	0.0014 (8)	−0.0081 (9)
C3	0.0462 (11)	0.0536 (12)	0.0419 (10)	−0.0013 (8)	0.0020 (8)	−0.0082 (9)
C4	0.0575 (13)	0.0777 (16)	0.0451 (12)	0.0008 (10)	−0.0005 (9)	0.0073 (11)
N1	0.0608 (11)	0.0606 (11)	0.0494 (10)	−0.0012 (8)	0.0025 (8)	−0.0022 (8)
N2	0.0645 (12)	0.0960 (15)	0.0422 (10)	−0.0040 (10)	−0.0054 (8)	−0.0101 (10)
C5	0.0695 (14)	0.0575 (12)	0.0366 (10)	−0.0065 (9)	0.0008 (9)	−0.0137 (9)
C6	0.0695 (16)	0.0932 (18)	0.0524 (13)	−0.0116 (12)	0.0033 (11)	−0.0199 (12)
C7	0.103 (2)	0.123 (2)	0.0616 (16)	−0.0383 (18)	0.0260 (16)	−0.0237 (16)
C8	0.158 (3)	0.105 (2)	0.0433 (14)	−0.033 (2)	0.0002 (18)	−0.0056 (14)
C9	0.129 (3)	0.107 (2)	0.0651 (17)	−0.0076 (19)	−0.0391 (19)	−0.0022 (16)
C10	0.0740 (17)	0.102 (2)	0.0656 (15)	−0.0096 (13)	−0.0142 (13)	−0.0141 (14)
C11	0.170 (3)	0.0617 (16)	0.0635 (16)	−0.0234 (16)	0.0113 (17)	−0.0244 (12)
N4	0.0828 (14)	0.0553 (11)	0.0452 (10)	−0.0049 (9)	0.0051 (9)	−0.0154 (8)
N3	0.0842 (13)	0.0542 (11)	0.0436 (9)	−0.0103 (8)	0.0035 (8)	−0.0115 (8)
O1	0.0992 (14)	0.0837 (13)	0.0688 (11)	0.0162 (10)	−0.0197 (10)	−0.0035 (9)
O2	0.1063 (15)	0.0742 (12)	0.0829 (13)	−0.0353 (10)	0.0259 (11)	−0.0125 (9)

Cl1—C1	1.905 (2)	C6—H6	0.9300
C1—C2	1.366 (3)	C7—C8	1.375 (5)
C1—N2	1.408 (3)	C7—H7	0.9300
C2—C3	1.560 (3)	C8—C9	1.368 (4)
C2—N4	1.573 (3)	C8—H8	0.9300
C3—N3	1.349 (3)	C9—C10	1.431 (4)
C3—N1	1.436 (2)	C9—H9	0.9300
C4—N1	1.324 (3)	C10—H10	0.9300
C4—N2	1.456 (3)	C11—N3	1.633 (3)
C4—H4	0.9300	C11—H11A	0.9600
C5—C6	1.380 (3)	C11—H11B	0.9600
C5—C10	1.388 (3)	C11—H11C	0.9600
C5—N3	1.488 (3)	N4—O1	1.226 (2)
C6—C7	1.430 (4)	N4—O2	1.242 (3)
C2—C1—N2	119.2 (2)	C6—C7—H7	119.4
C2—C1—Cl1	119.29 (17)	C9—C8—C7	118.4 (2)
N2—C1—Cl1	121.46 (16)	C9—C8—H8	120.8
C1—C2—C3	118.29 (17)	C7—C8—H8	120.8
C1—C2—N4	113.29 (18)	C8—C9—C10	121.4 (3)
C3—C2—N4	128.35 (16)	C8—C9—H9	119.3
N3—C3—N1	110.90 (18)	C10—C9—H9	119.3
N3—C3—C2	127.02 (16)	C5—C10—C9	120.0 (3)
N1—C3—C2	122.06 (17)	C5—C10—H10	120.0
N1—C4—N2	128.60 (19)	C9—C10—H10	120.0
N1—C4—H4	115.7	N3—C11—H11A	109.5
N2—C4—H4	115.7	N3—C11—H11B	109.5
C4—N1—C3	112.86 (19)	H11A—C11—H11B	109.5
C1—N2—C4	118.93 (18)	N3—C11—H11C	109.5
C6—C5—C10	118.8 (2)	H11A—C11—H11C	109.5
C6—C5—N3	121.0 (2)	H11B—C11—H11C	109.5
C10—C5—N3	120.1 (2)	O1—N4—O2	120.9 (2)
C5—C6—C7	120.2 (2)	O1—N4—C2	118.81 (18)
C5—C6—H6	119.9	O2—N4—C2	120.25 (19)
C7—C6—H6	119.9	C3—N3—C5	120.02 (17)
C8—C7—C6	121.2 (3)	C3—N3—C11	120.80 (17)
C8—C7—H7	119.4	C5—N3—C11	118.93 (17)