N,N'-(4-Chloro-benzyl-idene)dipyrimidin-2-amine.

The title compound, C(15)H(13)ClN(6), contains two pyrimidine rings and one benzene ring, where the dihedral angle between the planes through the pyrimidine rings is 81.57 (10)°, and those between the pyrimidine rings and the benzene ring are 84.02 (8) and 89.46 (7)°, indicating that the three rings are almost perpendicular. In the crystal, inter-molecular N-H⋯N hydrogen bonds link the mol-ecules into infinite chains along (100).

Related literature

For the biological activity of pyrimidine derivatives, see: Onal & Altral (1999 ▶); Ponticelli et al. (1999 ▶). For studies of the reactions of heterocyclic amines with aromatic aldehydes to prepare new ligands, see: Tabatabaee et al. (2006 ▶); Tabatabaee, Ghassemzadeh, Dehghan et al. (2007 ▶); Tabatabaee, Ghassemzadeh, Zarabi et al. (2007 ▶); Tabatabaee, Ghassemzadeh et al. (2008 ▶); Tabatabaee, Hakimi et al. (2008 ▶).

Experimental

Crystal data

C15H13ClN6

M = 312.76

Monoclinic,

a = 9.6030 (14) Å

b = 10.5706 (15) Å

c = 14.792 (2) Å

β = 100.331 (3)°

V = 1477.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 120 K

0.17 × 0.15 × 0.14 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.950, T max = 0.964

15899 measured reflections

3924 independent reflections

2429 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.163

S = 1.01

3924 reflections

207 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045243/ez2187sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045243/ez2187Isup2.hkl

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

C15H13ClN6	F(000) = 648
Mr = 312.76	Dx = 1.406 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 697 reflections
a = 9.6030 (14) Å	θ = 3–30°
b = 10.5706 (15) Å	µ = 0.26 mm−1
c = 14.792 (2) Å	T = 120 K
β = 100.331 (3)°	Prism, colorless
V = 1477.2 (4) Å3	0.17 × 0.15 × 0.14 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	3924 independent reflections
Radiation source: fine-focus sealed tube	2429 reflections with I > 2σ(I)
graphite	Rint = 0.063
ω scans	θmax = 29.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −13→13
Tmin = 0.950, Tmax = 0.964	k = −14→14
15899 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)] = 0.061	Hydrogen site location: mixed
wR(F2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.061P)2 + 1.85P] where P = (Fo2 + 2Fc2)/3
3924 reflections	(Δ/σ)max = 0.001
207 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.28 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	−0.02192 (8)	0.53784 (7)	0.18886 (5)	0.0355 (2)
N1	0.3768 (2)	0.1522 (2)	0.49990 (15)	0.0255 (5)
H1N	0.372 (3)	0.073 (3)	0.4970 (19)	0.026 (7)*
N2	0.5083 (2)	0.3334 (2)	0.53797 (15)	0.0288 (5)
N3	0.6177 (2)	0.13385 (19)	0.51466 (14)	0.0252 (5)
N4	0.1456 (2)	0.1274 (2)	0.53239 (15)	0.0271 (5)
H4N	0.100 (3)	0.085 (3)	0.490 (2)	0.026 (7)*
N5	0.1916 (2)	0.1776 (2)	0.68744 (15)	0.0297 (5)
N6	0.0426 (2)	0.0032 (2)	0.62930 (15)	0.0324 (5)
C1	0.2469 (3)	0.2170 (2)	0.51066 (17)	0.0236 (5)
H1A	0.2701	0.2771	0.5635	0.028*
C2	0.1814 (3)	0.2927 (2)	0.42613 (17)	0.0231 (5)
C3	0.2361 (3)	0.2959 (2)	0.34541 (18)	0.0281 (6)
H3A	0.3172	0.2468	0.3403	0.034*
C4	0.1729 (3)	0.3708 (3)	0.27187 (17)	0.0305 (6)
H4A	0.2106	0.3727	0.2168	0.037*
C5	0.0551 (3)	0.4423 (2)	0.27932 (17)	0.0257 (5)
C6	−0.0013 (3)	0.4405 (2)	0.35850 (18)	0.0274 (5)
H6A	−0.0824	0.4898	0.3633	0.033*
C7	0.0623 (3)	0.3653 (2)	0.43127 (17)	0.0263 (5)
H7A	0.0235	0.3635	0.4860	0.032*
C8	0.5041 (3)	0.2088 (2)	0.51871 (16)	0.0227 (5)
C9	0.6373 (3)	0.3841 (3)	0.5586 (2)	0.0346 (6)
H9A	0.6452	0.4713	0.5741	0.041*
C10	0.7596 (3)	0.3161 (3)	0.5585 (2)	0.0353 (7)
H10A	0.8505	0.3537	0.5745	0.042*
C11	0.7431 (3)	0.1905 (3)	0.53381 (18)	0.0295 (6)
H11A	0.8254	0.1421	0.5303	0.035*
C12	0.1273 (3)	0.1023 (3)	0.61980 (17)	0.0266 (5)
C13	0.1706 (3)	0.1484 (3)	0.77168 (19)	0.0346 (6)
H13A	0.2127	0.2005	0.8215	0.041*
C14	0.0906 (3)	0.0461 (3)	0.7899 (2)	0.0406 (7)
H14A	0.0802	0.0247	0.8507	0.049*
C15	0.0269 (3)	−0.0232 (3)	0.7149 (2)	0.0406 (7)
H15A	−0.0309	−0.0929	0.7247	0.049*

	U11	U22	U33	U12	U13	U23
Cl1	0.0406 (4)	0.0320 (4)	0.0312 (4)	0.0008 (3)	−0.0014 (3)	0.0066 (3)
N1	0.0227 (11)	0.0213 (11)	0.0316 (12)	−0.0002 (9)	0.0021 (9)	0.0004 (9)
N2	0.0303 (12)	0.0236 (11)	0.0335 (12)	−0.0039 (9)	0.0081 (9)	−0.0030 (9)
N3	0.0245 (11)	0.0236 (11)	0.0263 (11)	−0.0021 (9)	0.0016 (8)	−0.0015 (9)
N4	0.0272 (11)	0.0300 (12)	0.0229 (11)	−0.0074 (9)	0.0016 (9)	−0.0006 (9)
N5	0.0288 (12)	0.0333 (12)	0.0267 (11)	−0.0018 (10)	0.0043 (9)	−0.0002 (9)
N6	0.0310 (12)	0.0394 (13)	0.0256 (11)	−0.0081 (10)	0.0021 (9)	0.0041 (10)
C1	0.0227 (12)	0.0234 (12)	0.0238 (12)	−0.0010 (10)	0.0021 (9)	−0.0017 (10)
C2	0.0237 (12)	0.0221 (12)	0.0235 (12)	−0.0048 (10)	0.0042 (9)	0.0003 (10)
C3	0.0300 (14)	0.0268 (13)	0.0287 (13)	0.0029 (11)	0.0082 (11)	−0.0007 (11)
C4	0.0366 (15)	0.0345 (15)	0.0220 (12)	−0.0018 (12)	0.0098 (11)	−0.0007 (11)
C5	0.0288 (13)	0.0235 (12)	0.0230 (12)	−0.0030 (10)	−0.0001 (10)	−0.0001 (10)
C6	0.0238 (12)	0.0273 (13)	0.0300 (13)	0.0005 (10)	0.0023 (10)	−0.0025 (10)
C7	0.0246 (13)	0.0306 (13)	0.0245 (12)	−0.0010 (11)	0.0065 (10)	−0.0003 (10)
C8	0.0261 (13)	0.0221 (12)	0.0199 (12)	−0.0036 (10)	0.0039 (10)	0.0014 (10)
C9	0.0353 (15)	0.0254 (13)	0.0458 (16)	−0.0095 (12)	0.0147 (13)	−0.0094 (12)
C10	0.0306 (14)	0.0339 (15)	0.0437 (16)	−0.0109 (12)	0.0128 (12)	−0.0118 (13)
C11	0.0267 (13)	0.0306 (14)	0.0316 (14)	−0.0019 (11)	0.0065 (11)	−0.0009 (11)
C12	0.0225 (12)	0.0311 (14)	0.0256 (13)	0.0013 (11)	0.0028 (10)	0.0023 (11)
C13	0.0317 (15)	0.0410 (16)	0.0291 (14)	0.0026 (12)	0.0004 (11)	−0.0044 (12)
C14	0.0368 (16)	0.059 (2)	0.0258 (14)	−0.0061 (15)	0.0058 (12)	0.0057 (14)
C15	0.0346 (16)	0.0541 (19)	0.0330 (15)	−0.0126 (14)	0.0059 (12)	0.0119 (14)

Cl1—C5	1.732 (3)	C3—C4	1.394 (4)
N1—C8	1.345 (3)	C3—H3A	0.9500
N1—C1	1.456 (3)	C4—C5	1.381 (4)
N1—H1N	0.84 (3)	C4—H4A	0.9500
N2—C9	1.334 (3)	C5—C6	1.376 (4)
N2—C8	1.347 (3)	C6—C7	1.388 (4)
N3—C11	1.329 (3)	C6—H6A	0.9500
N3—C8	1.358 (3)	C7—H7A	0.9500
N4—C12	1.362 (3)	C9—C10	1.377 (4)
N4—C1	1.435 (3)	C9—H9A	0.9500
N4—H4N	0.83 (3)	C10—C11	1.378 (4)
N5—C13	1.334 (4)	C10—H10A	0.9500
N5—C12	1.339 (3)	C11—H11A	0.9500
N6—C15	1.331 (4)	C13—C14	1.381 (4)
N6—C12	1.349 (3)	C13—H13A	0.9500
C1—C2	1.523 (3)	C14—C15	1.378 (4)
C1—H1A	1.0000	C14—H14A	0.9500
C2—C3	1.389 (3)	C15—H15A	0.9500
C2—C7	1.390 (3)
C8—N1—C1	122.2 (2)	C5—C6—H6A	120.6
C8—N1—H1N	120 (2)	C7—C6—H6A	120.6
C1—N1—H1N	116 (2)	C6—C7—C2	121.7 (2)
C9—N2—C8	115.6 (2)	C6—C7—H7A	119.2
C11—N3—C8	115.6 (2)	C2—C7—H7A	119.2
C12—N4—C1	123.3 (2)	N1—C8—N2	118.0 (2)
C12—N4—H4N	118 (2)	N1—C8—N3	116.1 (2)
C1—N4—H4N	119 (2)	N2—C8—N3	125.9 (2)
C13—N5—C12	115.7 (2)	N2—C9—C10	123.2 (3)
C15—N6—C12	115.8 (2)	N2—C9—H9A	118.4
N4—C1—N1	110.0 (2)	C10—C9—H9A	118.4
N4—C1—C2	109.5 (2)	C9—C10—C11	116.5 (3)
N1—C1—C2	113.2 (2)	C9—C10—H10A	121.8
N4—C1—H1A	108.0	C11—C10—H10A	121.8
N1—C1—H1A	108.0	N3—C11—C10	123.1 (3)
C2—C1—H1A	108.0	N3—C11—H11A	118.4
C3—C2—C7	118.4 (2)	C10—C11—H11A	118.4
C3—C2—C1	123.7 (2)	N5—C12—N6	126.1 (2)
C7—C2—C1	117.9 (2)	N5—C12—N4	118.2 (2)
C2—C3—C4	120.4 (2)	N6—C12—N4	115.7 (2)
C2—C3—H3A	119.8	N5—C13—C14	123.1 (3)
C4—C3—H3A	119.8	N5—C13—H13A	118.5
C5—C4—C3	119.8 (2)	C14—C13—H13A	118.5
C5—C4—H4A	120.1	C15—C14—C13	116.2 (3)
C3—C4—H4A	120.1	C15—C14—H14A	121.9
C6—C5—C4	120.9 (2)	C13—C14—H14A	121.9
C6—C5—Cl1	119.1 (2)	N6—C15—C14	123.0 (3)
C4—C5—Cl1	120.0 (2)	N6—C15—H15A	118.5
C5—C6—C7	118.8 (2)	C14—C15—H15A	118.5
C12—N4—C1—N1	96.1 (3)	C1—N1—C8—N3	173.6 (2)
C12—N4—C1—C2	−139.0 (2)	C9—N2—C8—N1	178.2 (2)
C8—N1—C1—N4	−150.6 (2)	C9—N2—C8—N3	−3.1 (4)
C8—N1—C1—C2	86.6 (3)	C11—N3—C8—N1	−179.7 (2)
N4—C1—C2—C3	−120.7 (3)	C11—N3—C8—N2	1.6 (4)
N1—C1—C2—C3	2.5 (3)	C8—N2—C9—C10	1.5 (4)
N4—C1—C2—C7	61.2 (3)	N2—C9—C10—C11	1.2 (4)
N1—C1—C2—C7	−175.7 (2)	C8—N3—C11—C10	1.5 (4)
C7—C2—C3—C4	0.3 (4)	C9—C10—C11—N3	−2.8 (4)
C1—C2—C3—C4	−177.9 (2)	C13—N5—C12—N6	1.4 (4)
C2—C3—C4—C5	0.0 (4)	C13—N5—C12—N4	−179.7 (2)
C3—C4—C5—C6	−0.2 (4)	C15—N6—C12—N5	−2.5 (4)
C3—C4—C5—Cl1	178.8 (2)	C15—N6—C12—N4	178.6 (3)
C4—C5—C6—C7	0.1 (4)	C1—N4—C12—N5	10.1 (4)
Cl1—C5—C6—C7	−179.0 (2)	C1—N4—C12—N6	−170.9 (2)
C5—C6—C7—C2	0.3 (4)	C12—N5—C13—C14	1.4 (4)
C3—C2—C7—C6	−0.4 (4)	N5—C13—C14—C15	−2.8 (5)
C1—C2—C7—C6	177.8 (2)	C12—N6—C15—C14	0.8 (5)
C1—N1—C8—N2	−7.6 (3)	C13—C14—C15—N6	1.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N3i	0.84 (3)	2.20 (3)	3.033 (3)	174 (3)
N4—H4N···N6ii	0.83 (3)	2.24 (3)	3.057 (3)	172 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N3i	0.84 (3)	2.20 (3)	3.033 (3)	174 (3)
N4—H4N⋯N6ii	0.83 (3)	2.24 (3)	3.057 (3)	172 (3)

Symmetry codes: (i) ; (ii) .