N,N-Dimethyl-5-nitro-N,N-diphenyl-pyrimidine-4,6-diamine.

In the title compound, C(18)H(17)N(5)O(2), the pyrimidine ring makes dihedral angles of 66.09 (12), 71.39 (13) and 56.7 (3)° with two phenyl rings and the nitro group, respectively. The dihedral angle between the two phenyl rings is 44.05 (14)°.

Related literature

For applications of pyrimidine diamines, see: Barillari et al. (2001 ▶); Che et al. (2008 ▶); Itoh et al. (2004 ▶); Koppel & Robins (1958 ▶); Shi et al. (2011 ▶).

Experimental

Crystal data

C18H17N5O2

M = 335.37

Monoclinic,

a = 10.794 (2) Å

b = 7.0019 (14) Å

c = 23.650 (6) Å

β = 109.02 (3)°

V = 1689.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.50 × 0.12 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.956, T max = 0.991

15784 measured reflections

3843 independent reflections

2018 reflections with I > 2σ(I)

R int = 0.108

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.146

S = 1.05

3843 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.20 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/S1600536811035094/is2768sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035094/is2768Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035094/is2768Isup3.cml

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

C18H17N5O2	F(000) = 704
Mr = 335.37	Dx = 1.318 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 500 reflections
a = 10.794 (2) Å	θ = 3.1–27.5°
b = 7.0019 (14) Å	µ = 0.09 mm−1
c = 23.650 (6) Å	T = 293 K
β = 109.02 (3)°	Block, colorless
V = 1689.8 (6) Å3	0.50 × 0.12 × 0.10 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	3843 independent reflections
Radiation source: fine-focus sealed tube	2018 reflections with I > 2σ(I)
graphite	Rint = 0.108
Detector resolution: 10.00 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −14→13
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −9→9
Tmin = 0.956, Tmax = 0.991	l = −30→30
15784 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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0524P)2 + 0.0764P] where P = (Fo2 + 2Fc2)/3
3843 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.20 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
O1	0.84317 (18)	0.0703 (3)	0.35192 (9)	0.0577 (6)
O2	0.85674 (17)	0.2808 (3)	0.42079 (8)	0.0586 (6)
N1	0.5774 (2)	0.2175 (3)	0.41820 (9)	0.0435 (6)
N2	0.45045 (19)	0.3519 (3)	0.32882 (10)	0.0434 (6)
N3	0.52690 (19)	0.3954 (3)	0.24557 (9)	0.0412 (5)
N4	0.7997 (2)	0.2043 (3)	0.37282 (10)	0.0424 (6)
N5	0.74616 (19)	0.3627 (3)	0.25459 (9)	0.0393 (5)
C1	0.7275 (3)	−0.2635 (4)	0.44234 (13)	0.0553 (8)
H1	0.7216	−0.3782	0.4218	0.066*
C2	0.8135 (3)	−0.2471 (5)	0.49962 (14)	0.0639 (9)
H2	0.8663	−0.3498	0.5176	0.077*
C3	0.8210 (3)	−0.0796 (5)	0.53010 (13)	0.0678 (10)
H3	0.8784	−0.0692	0.5690	0.081*
C4	0.6587 (2)	0.0578 (4)	0.44551 (10)	0.0387 (6)
C5	0.6500 (3)	−0.1108 (4)	0.41512 (11)	0.0446 (7)
H5	0.5921	−0.1224	0.3763	0.054*
C6	0.7441 (3)	0.0745 (4)	0.50349 (12)	0.0562 (8)
H6	0.7496	0.1885	0.5243	0.067*
C7	0.4741 (3)	0.2699 (5)	0.44293 (13)	0.0705 (10)
H7A	0.4531	0.4028	0.4354	0.085*
H7B	0.5041	0.2470	0.4853	0.085*
H7C	0.3975	0.1943	0.4243	0.085*
C8	0.6703 (2)	0.2779 (3)	0.33805 (10)	0.0338 (6)
C9	0.5681 (2)	0.2799 (3)	0.36205 (11)	0.0362 (6)
C10	0.6494 (2)	0.3447 (3)	0.27970 (11)	0.0359 (6)
C11	0.4380 (2)	0.3965 (4)	0.27283 (13)	0.0456 (7)
H11	0.3545	0.4341	0.2493	0.055*
C12	0.8912 (3)	0.5770 (4)	0.32865 (12)	0.0461 (7)
H12	0.8181	0.6442	0.3303	0.055*
C13	0.9840 (3)	0.3278 (4)	0.28633 (12)	0.0474 (7)
H13	0.9742	0.2256	0.2601	0.057*
C14	1.0143 (3)	0.6310 (4)	0.36414 (13)	0.0573 (8)
H14	1.0246	0.7332	0.3904	0.069*
C15	1.1078 (3)	0.3861 (4)	0.32153 (13)	0.0573 (8)
H15	1.1815	0.3241	0.3184	0.069*
C16	1.1223 (3)	0.5339 (5)	0.36078 (13)	0.0604 (9)
H16	1.2056	0.5690	0.3853	0.072*
C17	0.8759 (2)	0.4228 (3)	0.29054 (10)	0.0365 (6)
C18	0.7094 (3)	0.3940 (4)	0.19040 (10)	0.0503 (7)
H18A	0.6509	0.2945	0.1697	0.060*
H18B	0.7865	0.3927	0.1786	0.060*
H18C	0.6664	0.5154	0.1805	0.060*

	U11	U22	U33	U12	U13	U23
O1	0.0466 (12)	0.0511 (12)	0.0785 (14)	0.0176 (10)	0.0247 (11)	0.0139 (11)
O2	0.0418 (11)	0.0717 (14)	0.0505 (11)	−0.0089 (10)	−0.0010 (9)	0.0050 (11)
N1	0.0423 (12)	0.0468 (13)	0.0451 (12)	0.0077 (11)	0.0194 (10)	0.0064 (11)
N2	0.0315 (12)	0.0430 (13)	0.0557 (14)	0.0047 (10)	0.0143 (10)	0.0090 (11)
N3	0.0313 (12)	0.0410 (12)	0.0469 (12)	0.0030 (10)	0.0066 (10)	0.0064 (10)
N4	0.0323 (12)	0.0434 (14)	0.0507 (14)	0.0013 (11)	0.0126 (11)	0.0124 (12)
N5	0.0314 (11)	0.0470 (13)	0.0389 (12)	0.0007 (10)	0.0108 (10)	0.0015 (10)
C1	0.065 (2)	0.0434 (16)	0.0620 (18)	0.0039 (15)	0.0270 (16)	0.0043 (15)
C2	0.059 (2)	0.064 (2)	0.066 (2)	0.0128 (17)	0.0162 (16)	0.0262 (18)
C3	0.058 (2)	0.084 (2)	0.0471 (17)	−0.0004 (19)	−0.0025 (15)	0.0157 (18)
C4	0.0346 (14)	0.0434 (15)	0.0364 (13)	−0.0024 (12)	0.0091 (11)	0.0021 (12)
C5	0.0439 (15)	0.0456 (17)	0.0420 (14)	−0.0041 (13)	0.0107 (12)	0.0034 (13)
C6	0.0603 (19)	0.0576 (19)	0.0424 (15)	−0.0027 (15)	0.0054 (14)	−0.0024 (14)
C7	0.069 (2)	0.092 (2)	0.0630 (19)	0.0289 (19)	0.0377 (17)	0.0118 (18)
C8	0.0234 (12)	0.0313 (13)	0.0417 (14)	0.0007 (10)	0.0037 (11)	0.0031 (11)
C9	0.0312 (13)	0.0316 (13)	0.0450 (14)	0.0009 (11)	0.0112 (12)	−0.0002 (12)
C10	0.0302 (13)	0.0311 (13)	0.0424 (14)	−0.0017 (11)	0.0063 (12)	−0.0019 (11)
C11	0.0287 (14)	0.0426 (16)	0.0610 (18)	0.0040 (12)	0.0087 (13)	0.0123 (14)
C12	0.0433 (16)	0.0426 (15)	0.0566 (16)	−0.0036 (13)	0.0219 (13)	−0.0039 (14)
C13	0.0416 (15)	0.0460 (16)	0.0568 (16)	0.0059 (13)	0.0188 (13)	−0.0010 (13)
C14	0.059 (2)	0.0513 (17)	0.0600 (18)	−0.0148 (16)	0.0176 (15)	−0.0084 (15)
C15	0.0347 (15)	0.064 (2)	0.073 (2)	0.0080 (15)	0.0174 (15)	0.0161 (17)
C16	0.0452 (18)	0.068 (2)	0.0580 (18)	−0.0170 (17)	0.0033 (15)	0.0101 (17)
C17	0.0321 (13)	0.0390 (14)	0.0393 (13)	−0.0003 (12)	0.0129 (11)	0.0038 (12)
C18	0.0465 (16)	0.0653 (19)	0.0403 (15)	0.0101 (15)	0.0157 (13)	0.0026 (14)

O1—N4	1.223 (3)	C5—H5	0.9300
O2—N4	1.224 (3)	C6—H6	0.9300
N1—C9	1.370 (3)	C7—H7A	0.9600
N1—C4	1.438 (3)	C7—H7B	0.9600
N1—C7	1.464 (3)	C7—H7C	0.9600
N2—C11	1.324 (3)	C8—C9	1.395 (3)
N2—C9	1.355 (3)	C8—C10	1.404 (3)
N3—C11	1.319 (3)	C11—H11	0.9300
N3—C10	1.353 (3)	C12—C14	1.374 (4)
N4—C8	1.464 (3)	C12—C17	1.382 (3)
N5—C10	1.366 (3)	C12—H12	0.9300
N5—C17	1.444 (3)	C13—C17	1.375 (4)
N5—C18	1.455 (3)	C13—C15	1.385 (4)
C1—C2	1.375 (4)	C13—H13	0.9300
C1—C5	1.381 (4)	C14—C16	1.374 (4)
C1—H1	0.9300	C14—H14	0.9300
C2—C3	1.365 (4)	C15—C16	1.365 (4)
C2—H2	0.9300	C15—H15	0.9300
C3—C6	1.382 (4)	C16—H16	0.9300
C3—H3	0.9300	C18—H18A	0.9600
C4—C5	1.369 (3)	C18—H18B	0.9600
C4—C6	1.386 (3)	C18—H18C	0.9600
C9—N1—C4	121.6 (2)	C9—C8—N4	120.7 (2)
C9—N1—C7	118.9 (2)	C10—C8—N4	119.2 (2)
C4—N1—C7	116.6 (2)	N2—C9—N1	116.1 (2)
C11—N2—C9	116.0 (2)	N2—C9—C8	118.9 (2)
C11—N3—C10	115.8 (2)	N1—C9—C8	125.0 (2)
O1—N4—O2	124.5 (2)	N3—C10—N5	117.0 (2)
O1—N4—C8	117.7 (2)	N3—C10—C8	119.1 (2)
O2—N4—C8	117.8 (2)	N5—C10—C8	123.9 (2)
C10—N5—C17	120.2 (2)	N3—C11—N2	129.4 (2)
C10—N5—C18	118.7 (2)	N3—C11—H11	115.3
C17—N5—C18	116.9 (2)	N2—C11—H11	115.3
C2—C1—C5	120.4 (3)	C14—C12—C17	120.0 (3)
C2—C1—H1	119.8	C14—C12—H12	120.0
C5—C1—H1	119.8	C17—C12—H12	120.0
C3—C2—C1	119.8 (3)	C17—C13—C15	119.3 (3)
C3—C2—H2	120.1	C17—C13—H13	120.4
C1—C2—H2	120.1	C15—C13—H13	120.4
C2—C3—C6	120.5 (3)	C16—C14—C12	119.9 (3)
C2—C3—H3	119.8	C16—C14—H14	120.0
C6—C3—H3	119.8	C12—C14—H14	120.0
C5—C4—C6	120.1 (2)	C16—C15—C13	120.5 (3)
C5—C4—N1	120.5 (2)	C16—C15—H15	119.8
C6—C4—N1	119.4 (2)	C13—C15—H15	119.8
C4—C5—C1	119.7 (2)	C15—C16—C14	120.2 (3)
C4—C5—H5	120.1	C15—C16—H16	119.9
C1—C5—H5	120.1	C14—C16—H16	119.9
C3—C6—C4	119.5 (3)	C13—C17—C12	120.1 (2)
C3—C6—H6	120.3	C13—C17—N5	120.0 (2)
C4—C6—H6	120.3	C12—C17—N5	119.9 (2)
N1—C7—H7A	109.5	N5—C18—H18A	109.5
N1—C7—H7B	109.5	N5—C18—H18B	109.5
H7A—C7—H7B	109.5	H18A—C18—H18B	109.5
N1—C7—H7C	109.5	N5—C18—H18C	109.5
H7A—C7—H7C	109.5	H18A—C18—H18C	109.5
H7B—C7—H7C	109.5	H18B—C18—H18C	109.5
C9—C8—C10	120.1 (2)