5-[(3,5-Dichloro-anilino)meth-yl]-N-(3,5-dichloro-phen-yl)-6-methyl-2-phenyl-pyrimidin-4-amine.

In the title compound, C24H18Cl4N4, the pyrimidine ring makes dihedral angles of 19.1 (2), 4.1 (2) and 67.5 (2)°, respectively, with phenyl and two benzene rings, and the mol-ecular conformation is stabilized by an intra-molecular N-H⋯N hydrogen bond closing a six-membered ring with an S(6) motif. In the crystal, a pair of inter-molecular N-H⋯N hydrogen bonds connect two mol-ecules, forming inversion dimers with R2(2)(12) motifs. C-H⋯π inter-actions links the dimers into a chain running along the a-axis direction. There are also π-π stacking inter-actions [centroid-centroid distance = 3.666 (4) Å] between the benzene rings of adjacent chains.

Related literature

For the anti­bacterial activity of 6-methyl-2-phenyl-5-substituted pyrimidine derivatives, see: Cieplik et al. (2003 ▶, 2008 ▶). For related structures, see: Cieplik et al. (2006 ▶, 2012 ▶).

Experimental

Crystal data

C24H18Cl4N4

M = 504.22

Triclinic,

a = 8.267 (3) Å

b = 11.271 (4) Å

c = 12.788 (4) Å

α = 76.53 (5)°

β = 78.95 (5)°

γ = 81.42 (5)°

V = 1130.4 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.54 mm−1

T = 85 K

0.23 × 0.14 × 0.08 mm

Data collection

Oxford Xcalibur PX with Onyx CCD diffractometer

19215 measured reflections

8041 independent reflections

5082 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.100

S = 1.03

8041 reflections

296 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.75 e Å−3

Δρmin = −0.41 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681204665X/is5217sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204665X/is5217Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204665X/is5217Isup3.cml

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

C24H18Cl4N4	Z = 2
Mr = 504.22	F(000) = 516
Triclinic, P1	Dx = 1.481 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.267 (3) Å	Cell parameters from 12129 reflections
b = 11.271 (4) Å	θ = 4.3–32.6°
c = 12.788 (4) Å	µ = 0.54 mm−1
α = 76.53 (5)°	T = 85 K
β = 78.95 (5)°	Plate, yellow
γ = 81.42 (5)°	0.23 × 0.14 × 0.08 mm
V = 1130.4 (7) Å3

Oxford Xcalibur PX with Onyx CCD diffractometer	5082 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.041
Graphite monochromator	θmax = 32.6°, θmin = 4.3°
φ and ω scans	h = −12→12
19215 measured reflections	k = −17→14
8041 independent reflections	l = −19→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.041P)2] where P = (Fo2 + 2Fc2)/3
8041 reflections	(Δ/σ)max = 0.001
296 parameters	Δρmax = 0.75 e Å−3
0 restraints	Δρmin = −0.41 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
N1	0.26701 (17)	0.40318 (13)	0.58153 (11)	0.0170 (3)
C2	0.1469 (2)	0.48670 (15)	0.61481 (13)	0.0155 (3)
C21	0.0585 (2)	0.45458 (15)	0.72891 (13)	0.0168 (3)
C22	0.0633 (2)	0.33165 (16)	0.78508 (14)	0.0198 (3)
H22	0.1220	0.2687	0.7500	0.024*
C23	−0.0180 (2)	0.30171 (17)	0.89231 (14)	0.0221 (4)
H23	−0.0157	0.2183	0.9297	0.026*
C24	−0.1019 (2)	0.39319 (18)	0.94450 (14)	0.0240 (4)
H24	−0.1558	0.3725	1.0179	0.029*
C25	−0.1074 (2)	0.51528 (17)	0.88948 (14)	0.0225 (4)
H25	−0.1648	0.5779	0.9254	0.027*
C26	−0.0289 (2)	0.54593 (16)	0.78179 (13)	0.0196 (3)
H26	−0.0347	0.6293	0.7441	0.024*
N3	0.09912 (17)	0.59756 (13)	0.55551 (11)	0.0165 (3)
C4	0.1808 (2)	0.62576 (15)	0.45336 (13)	0.0163 (3)
N4	0.14556 (18)	0.73910 (13)	0.38923 (12)	0.0194 (3)
H4	0.215 (3)	0.7569 (17)	0.3309 (16)	0.023*
C41	0.0217 (2)	0.83536 (15)	0.40395 (13)	0.0178 (3)
C42	0.0187 (2)	0.93460 (15)	0.31393 (14)	0.0192 (3)
H42	0.0956	0.9318	0.2488	0.023*
Cl43	−0.09392 (6)	1.15946 (4)	0.20955 (4)	0.03017 (12)
C43	−0.0962 (2)	1.03605 (16)	0.32040 (14)	0.0213 (4)
C44	−0.2132 (2)	1.04310 (16)	0.41377 (15)	0.0223 (4)
H44	−0.2922	1.1130	0.4176	0.027*
Cl45	−0.35266 (6)	0.95034 (4)	0.61925 (4)	0.02676 (11)
C45	−0.2088 (2)	0.94317 (16)	0.50077 (14)	0.0206 (4)
C46	−0.0948 (2)	0.83949 (16)	0.49892 (14)	0.0200 (3)
H46	−0.0956	0.7731	0.5604	0.024*
C5	0.3055 (2)	0.54229 (15)	0.40746 (13)	0.0162 (3)
C57	0.3832 (2)	0.57235 (15)	0.28867 (13)	0.0179 (3)
H571	0.4663	0.5036	0.2719	0.021*
H572	0.2965	0.5818	0.2427	0.021*
N5	0.46367 (19)	0.68541 (14)	0.26224 (11)	0.0183 (3)
H5	0.528 (3)	0.6832 (18)	0.3034 (16)	0.022*
C51	0.5219 (2)	0.73560 (15)	0.15245 (13)	0.0164 (3)
C52	0.4940 (2)	0.68769 (15)	0.06663 (13)	0.0175 (3)
H52	0.4382	0.6164	0.0808	0.021*
Cl53	0.50653 (6)	0.68927 (4)	−0.14584 (3)	0.02527 (10)
C53	0.5497 (2)	0.74650 (16)	−0.03970 (13)	0.0184 (3)
C54	0.6378 (2)	0.84794 (16)	−0.06569 (13)	0.0197 (3)
H54	0.6773	0.8851	−0.1390	0.024*
Cl55	0.77628 (5)	1.01867 (4)	−0.00557 (4)	0.02456 (10)
C55	0.6651 (2)	0.89215 (15)	0.02165 (14)	0.0184 (3)
C56	0.6071 (2)	0.84064 (15)	0.12903 (13)	0.0182 (3)
H56	0.6244	0.8755	0.1863	0.022*
C6	0.3436 (2)	0.43092 (15)	0.47665 (13)	0.0165 (3)
C61	0.4707 (2)	0.33156 (16)	0.44054 (14)	0.0209 (3)
H611	0.4296	0.2973	0.3881	0.031*
H612	0.4904	0.2665	0.5039	0.031*
H613	0.5745	0.3663	0.4061	0.031*

	U11	U22	U33	U12	U13	U23
N1	0.0158 (7)	0.0178 (7)	0.0174 (7)	−0.0026 (6)	−0.0028 (5)	−0.0029 (5)
C2	0.0135 (7)	0.0169 (8)	0.0161 (7)	−0.0038 (6)	−0.0020 (6)	−0.0024 (6)
C21	0.0139 (7)	0.0201 (8)	0.0159 (7)	−0.0034 (6)	−0.0027 (6)	−0.0016 (6)
C22	0.0166 (8)	0.0209 (9)	0.0209 (8)	−0.0029 (7)	−0.0032 (6)	−0.0017 (7)
C23	0.0180 (8)	0.0247 (9)	0.0207 (8)	−0.0058 (7)	−0.0045 (7)	0.0041 (7)
C24	0.0185 (8)	0.0361 (11)	0.0149 (8)	−0.0052 (8)	−0.0015 (6)	0.0000 (7)
C25	0.0184 (8)	0.0294 (10)	0.0189 (8)	−0.0003 (7)	−0.0014 (6)	−0.0063 (7)
C26	0.0197 (8)	0.0203 (9)	0.0183 (8)	−0.0021 (7)	−0.0029 (6)	−0.0031 (6)
N3	0.0139 (6)	0.0170 (7)	0.0172 (6)	−0.0017 (6)	−0.0023 (5)	−0.0012 (5)
C4	0.0147 (7)	0.0165 (8)	0.0170 (7)	−0.0032 (6)	−0.0036 (6)	−0.0002 (6)
N4	0.0181 (7)	0.0200 (7)	0.0157 (7)	0.0001 (6)	0.0008 (5)	0.0007 (6)
C41	0.0156 (8)	0.0184 (8)	0.0194 (8)	−0.0025 (7)	−0.0029 (6)	−0.0035 (6)
C42	0.0210 (8)	0.0173 (8)	0.0188 (8)	−0.0031 (7)	−0.0029 (6)	−0.0024 (6)
Cl43	0.0383 (3)	0.0190 (2)	0.0286 (2)	0.0018 (2)	−0.00697 (19)	0.00210 (17)
C43	0.0238 (9)	0.0152 (8)	0.0251 (9)	−0.0019 (7)	−0.0083 (7)	−0.0013 (7)
C44	0.0196 (8)	0.0182 (9)	0.0295 (9)	−0.0001 (7)	−0.0060 (7)	−0.0057 (7)
Cl45	0.0206 (2)	0.0292 (2)	0.0291 (2)	−0.00330 (18)	0.00381 (17)	−0.00958 (18)
C45	0.0165 (8)	0.0229 (9)	0.0230 (8)	−0.0040 (7)	−0.0004 (6)	−0.0073 (7)
C46	0.0183 (8)	0.0193 (8)	0.0209 (8)	−0.0034 (7)	−0.0027 (6)	−0.0009 (6)
C5	0.0147 (7)	0.0186 (8)	0.0148 (7)	−0.0053 (7)	−0.0002 (6)	−0.0024 (6)
C57	0.0184 (8)	0.0189 (8)	0.0160 (8)	−0.0042 (7)	−0.0005 (6)	−0.0037 (6)
N5	0.0184 (7)	0.0220 (7)	0.0141 (7)	−0.0063 (6)	−0.0025 (5)	−0.0005 (5)
C51	0.0131 (7)	0.0168 (8)	0.0163 (7)	0.0002 (6)	0.0007 (6)	−0.0012 (6)
C52	0.0154 (8)	0.0170 (8)	0.0190 (8)	−0.0021 (6)	−0.0013 (6)	−0.0028 (6)
Cl53	0.0286 (2)	0.0314 (2)	0.01672 (19)	−0.00648 (19)	−0.00104 (16)	−0.00705 (17)
C53	0.0177 (8)	0.0198 (8)	0.0170 (8)	0.0003 (7)	−0.0022 (6)	−0.0042 (6)
C54	0.0166 (8)	0.0220 (9)	0.0161 (8)	−0.0003 (7)	0.0017 (6)	0.0001 (6)
Cl55	0.0211 (2)	0.0214 (2)	0.0291 (2)	−0.00812 (17)	0.00107 (17)	−0.00176 (17)
C55	0.0131 (7)	0.0160 (8)	0.0238 (8)	−0.0027 (6)	0.0005 (6)	−0.0016 (6)
C56	0.0162 (8)	0.0181 (8)	0.0197 (8)	−0.0010 (7)	−0.0023 (6)	−0.0037 (6)
C6	0.0147 (7)	0.0185 (8)	0.0177 (8)	−0.0032 (6)	−0.0032 (6)	−0.0053 (6)
C61	0.0220 (9)	0.0211 (9)	0.0185 (8)	−0.0016 (7)	−0.0024 (7)	−0.0034 (7)

N1—C2	1.341 (2)	C44—H44	0.9500
N1—C6	1.355 (2)	Cl45—C45	1.748 (2)
C2—N3	1.348 (2)	C45—C46	1.389 (3)
C2—C21	1.490 (2)	C46—H46	0.9500
C21—C26	1.398 (2)	C5—C6	1.389 (2)
C21—C22	1.403 (2)	C5—C57	1.512 (2)
C22—C23	1.394 (2)	C57—N5	1.465 (2)
C22—H22	0.9500	C57—H571	0.9900
C23—C24	1.386 (3)	C57—H572	0.9900
C23—H23	0.9500	N5—C51	1.405 (2)
C24—C25	1.390 (3)	N5—H5	0.81 (2)
C24—H24	0.9500	C51—C52	1.400 (2)
C25—C26	1.393 (2)	C51—C56	1.411 (2)
C25—H25	0.9500	C52—C53	1.390 (2)
C26—H26	0.9500	C52—H52	0.9500
N3—C4	1.340 (2)	Cl53—C53	1.7457 (18)
C4—N4	1.372 (2)	C53—C54	1.388 (2)
C4—C5	1.425 (2)	C54—C55	1.391 (2)
N4—C41	1.397 (2)	C54—H54	0.9500
N4—H4	0.85 (2)	Cl55—C55	1.7428 (19)
C41—C46	1.403 (2)	C55—C56	1.383 (2)
C41—C42	1.407 (2)	C56—H56	0.9500
C42—C43	1.381 (3)	C6—C61	1.508 (2)
C42—H42	0.9500	C61—H611	0.9800
Cl43—C43	1.739 (2)	C61—H612	0.9800
C43—C44	1.395 (3)	C61—H613	0.9800
C44—C45	1.388 (3)
C2—N1—C6	116.77 (15)	C46—C45—Cl45	118.71 (14)
N1—C2—N3	126.46 (14)	C45—C46—C41	118.27 (16)
N1—C2—C21	116.89 (15)	C45—C46—H46	120.9
N3—C2—C21	116.64 (15)	C41—C46—H46	120.9
C26—C21—C22	119.13 (15)	C6—C5—C4	115.95 (14)
C26—C21—C2	120.75 (15)	C6—C5—C57	122.90 (15)
C22—C21—C2	120.12 (16)	C4—C5—C57	121.06 (15)
C23—C22—C21	120.12 (17)	N5—C57—C5	111.59 (14)
C23—C22—H22	119.9	N5—C57—H571	109.3
C21—C22—H22	119.9	C5—C57—H571	109.3
C24—C23—C22	120.26 (17)	N5—C57—H572	109.3
C24—C23—H23	119.9	C5—C57—H572	109.3
C22—C23—H23	119.9	H571—C57—H572	108.0
C23—C24—C25	120.02 (16)	C51—N5—C57	118.79 (14)
C23—C24—H24	120.0	C51—N5—H5	114.4 (14)
C25—C24—H24	120.0	C57—N5—H5	111.4 (14)
C24—C25—C26	120.14 (17)	C52—C51—N5	122.57 (15)
C24—C25—H25	119.9	C52—C51—C56	119.43 (15)
C26—C25—H25	119.9	N5—C51—C56	117.97 (15)
C25—C26—C21	120.32 (17)	C53—C52—C51	118.68 (15)
C25—C26—H26	119.8	C53—C52—H52	120.7
C21—C26—H26	119.8	C51—C52—H52	120.7
C4—N3—C2	116.02 (15)	C54—C53—C52	123.42 (16)
N3—C4—N4	119.79 (16)	C54—C53—Cl53	118.48 (13)
N3—C4—C5	122.54 (15)	C52—C53—Cl53	118.10 (13)
N4—C4—C5	117.68 (15)	C53—C54—C55	116.30 (15)
C4—N4—C41	132.19 (15)	C53—C54—H54	121.8
C4—N4—H4	114.8 (13)	C55—C54—H54	121.8
C41—N4—H4	112.9 (13)	C56—C55—C54	122.95 (16)
N4—C41—C46	125.49 (16)	C56—C55—Cl55	118.53 (14)
N4—C41—C42	115.01 (15)	C54—C55—Cl55	118.52 (13)
C46—C41—C42	119.50 (17)	C55—C56—C51	119.14 (16)
C43—C42—C41	119.91 (16)	C55—C56—H56	120.4
C43—C42—H42	120.0	C51—C56—H56	120.4
C41—C42—H42	120.0	N1—C6—C5	122.14 (16)
C42—C43—C44	121.94 (17)	N1—C6—C61	115.13 (15)
C42—C43—Cl43	119.13 (14)	C5—C6—C61	122.73 (15)
C44—C43—Cl43	118.93 (14)	C6—C61—H611	109.5
C45—C44—C43	116.89 (17)	C6—C61—H612	109.5
C45—C44—H44	121.6	H611—C61—H612	109.5
C43—C44—H44	121.6	C6—C61—H613	109.5
C44—C45—C46	123.47 (17)	H611—C61—H613	109.5
C44—C45—Cl45	117.81 (15)	H612—C61—H613	109.5
C6—N1—C2—N3	−2.8 (2)	Cl45—C45—C46—C41	−179.12 (13)
C6—N1—C2—C21	177.92 (14)	N4—C41—C46—C45	179.14 (16)
N1—C2—C21—C26	159.86 (15)	C42—C41—C46—C45	−0.6 (2)
N3—C2—C21—C26	−19.5 (2)	N3—C4—C5—C6	−2.8 (2)
N1—C2—C21—C22	−19.6 (2)	N4—C4—C5—C6	176.84 (15)
N3—C2—C21—C22	161.04 (15)	N3—C4—C5—C57	173.95 (15)
C26—C21—C22—C23	−0.2 (2)	N4—C4—C5—C57	−6.4 (2)
C2—C21—C22—C23	179.27 (15)	C6—C5—C57—N5	−124.24 (17)
C21—C22—C23—C24	−0.9 (3)	C4—C5—C57—N5	59.3 (2)
C22—C23—C24—C25	0.9 (3)	C5—C57—N5—C51	−171.30 (14)
C23—C24—C25—C26	0.1 (3)	C57—N5—C51—C52	5.4 (2)
C24—C25—C26—C21	−1.2 (3)	C57—N5—C51—C56	−176.58 (15)
C22—C21—C26—C25	1.2 (3)	N5—C51—C52—C53	177.13 (16)
C2—C21—C26—C25	−178.25 (16)	C56—C51—C52—C53	−0.8 (2)
N1—C2—N3—C4	0.1 (2)	C51—C52—C53—C54	2.7 (3)
C21—C2—N3—C4	179.38 (14)	C51—C52—C53—Cl53	−177.45 (13)
C2—N3—C4—N4	−176.81 (14)	C52—C53—C54—C55	−1.9 (3)
C2—N3—C4—C5	2.8 (2)	Cl53—C53—C54—C55	178.27 (13)
N3—C4—N4—C41	−8.2 (3)	C53—C54—C55—C56	−0.8 (3)
C5—C4—N4—C41	172.14 (17)	C53—C54—C55—Cl55	179.54 (13)
C4—N4—C41—C46	5.3 (3)	C54—C55—C56—C51	2.6 (3)
C4—N4—C41—C42	−174.89 (17)	Cl55—C55—C56—C51	−177.80 (13)
N4—C41—C42—C43	−178.50 (16)	C52—C51—C56—C55	−1.7 (2)
C46—C41—C42—C43	1.3 (2)	N5—C51—C56—C55	−179.73 (15)
C41—C42—C43—C44	−1.1 (3)	C2—N1—C6—C5	2.7 (2)
C41—C42—C43—Cl43	178.19 (13)	C2—N1—C6—C61	−176.51 (14)
C42—C43—C44—C45	0.2 (3)	C4—C5—C6—N1	−0.1 (2)
Cl43—C43—C44—C45	−179.07 (13)	C57—C5—C6—N1	−176.77 (15)
C43—C44—C45—C46	0.5 (3)	C4—C5—C6—C61	179.00 (15)
C43—C44—C45—Cl45	179.35 (13)	C57—C5—C6—C61	2.3 (2)
C44—C45—C46—C41	−0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N5	0.85 (2)	2.19 (2)	2.875 (3)	137.6 (17)
N5—H5···N1i	0.81 (2)	2.40 (2)	3.171 (3)	158.1 (19)
C57—H572···Cg1ii	0.99	2.65	3.62 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C21–C26 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N5	0.85 (2)	2.19 (2)	2.875 (3)	137.6 (17)
N5—H5⋯N1i	0.81 (2)	2.40 (2)	3.171 (3)	158.1 (19)
C57—H572⋯Cg1ii	0.99	2.65	3.62 (2)	166

Symmetry codes: (i) ; (ii) .