Two polymorphic forms of N-(4-chloro­phenyl)-5-[(4-chlorophenyl)aminomethyl]-6-methyl-2-phenyl­pyrimidin-4-amine

Cieplik, J.; Pluta, J.; Bryndal, I.; Lis, T.

doi:10.1107/S0108270106010390

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Two polymorphic forms of N-(4-chlorophenyl)-5-[(4-chlorophenyl)aminomethyl]-6-methyl-2-phenylpyrimidin-4-amine

J. Cieplik, J. Pluta, I. Bryndal and T. Lis

Two polymorphic forms of the title compound, C₂₄H₂₀Cl₂N₄, were obtained and characterized using X-ray crystal structure analysis. Colourless crystals of polymorph (Ia) were obtained from the oily mother residue. Recrystallization of polymorph (Ia) from an acetone-methanol mixture resulted in pale-yellow crystals of polymorph (Ib). The major feature distinguishing the two polymorphic forms is their interaction modes, and hence their packing arrangements. In the crystal structure of polymorph (Ia), there are N-H

N hydrogen bonds and also aromatic [pi]

stacking interactions between molecules. The molecules of polymorph (Ib) are linked by N-H

Cl hydrogen bonds only.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106010390/sq3007sup1.cif Contains datablocks global, Ia, Ib
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270106010390/sq3007Iasup2.hkl Contains datablock Ia
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270106010390/sq3007Ibsup3.hkl Contains datablock Ib

CCDC references: 609416; 609417

Comment top

Pyrimidine derivatives have very interesting biological properties and many applications in the areas of pharmaceuticals. For example, alkoxy- and amino-substitued O⁶-benzyloxy-5-nitropyrimidines are important as potential inhibitors of the human DNA-repair protein O⁶-alkylguanine-DNA-transferase (Quesada et al., 2002; Glidewell et al., 2003). Several pyrimidine derivatives have been developed as agrochemicals (Maeno et al., 1990), antiviral agents, such as AZT, which is the most widely used anti-HIV drug (Gilchrist, 1997), or antifolate drugs, such as TMP and DHFR (Feeney, 2000).

In order to discover more active pyrimidine compounds displaying immunomodulatory activity, we synthesized new 6-methyl-2-phenyl-5-substitued pyrimidine derivatives (Cieplik et al., 1995). We report here the structures of two polymorphic forms of N-(4-chlorophenyl)-5-{[(4-chlorophenyl)amino]methyl}-6-methyl-2-phenylpyrimidin-4-amine, (Ia) and (Ib).

The polymorphs (Ia) (Fig. 1) and (Ib) (Fig. 2) crystallize in space group Pbca with Z = 8 and in P2₁/c with Z = 4, respectively. The bond lengths and angles for (Ia) and (Ib) are in accordance with anticipated values (Reference for standard values?). However, pronounced differences between these polymorphs are apparent in the conformation of the 4-chlorophenylamino group about atom C51.

In both cases, the orientation of N amide atoms with respect to each other is the result of an intramolecular N—H···N hydrogen bond between atoms N4 and N5, which generates an S(6) motif (Bernstein et al., 1995). The C—N distances are in the ranges 1.329 (3)–1.360 (3) Å in (Ia) and 1.329 (3)–1.353 (3) Å in (Ib) (Table 1), with no significant bond fixation within the pyrimidine ring. In addition, the pyrimidine ring distances are comparable with the corresponding bonds in 4,6-disubstitued 2-aminopyrimidines (Quesada et al., 2004). The phenyl ring is nearly coplanar with the pyrimidine ring: the angle between the least-squares planes through the pyrimidine and phenyl rings is 5.2 (2)° in (Ia) and 6.4 (2)° in (Ib). Aromatic atom C41 of the N-(4-chlorophenyl)-4-amine group is also nearly coplanar with the pyrimidine ring, whereas atom C51 of the 5-[(4-chlorophenyl)amino]methyl group deviates from the pyrimidine ring plane by −1.20 (1) Å in (Ia) and −2.19 (1) Å in (Ib). The C5—C57—N5—C51 torsion angle describing the orientation of aromatic atom C51 with respect to the pyrimidine atom C5 is 179.8 (2)° in (Ia) and 80.5 (2)° in (Ib).

The molecules of (Ia) are linked by N—H···N hydrogen bonds (Table 2), with amide atom N5 as a donor and ring atom N1 of the molecule at (x − 1/2, y, −z + 1/2) as acceptor in this linkage. Propagation of the hydrogen-bonding C(7) motif generates a chain running along the a axis (Fig. 3). Between pyrimidine rings of adjacent molecules within a chain there is also an aromatic π–π stacking interaction, with an interplanar spacing of 3.47 (4) Å, a centroid-to-centroid separation of 3.71 (3) Å and a centroid offset of 1.31 Å. These chains run through each unit cell, but there is no direction-specific interaction between adjacent chains.

It is interesting to note that the aromatic π–π stacking interactions found in (Ia) are absent in the structure of (Ib) and molecules are linked by N—H···Cl hydrogen bonds only (Table 2). Amide atom N5 acts as a hydrogen-bond donor to atom Cl4 in the molecule at (x, −y + 1/2, z − 1/2). This hydrogen-bond motif, which can be described as C(11), generates a chain running along the c axis (Fig. 4).

Experimental top

Compound (I) was obtained as a yellowish oil using the procedure described previously by Cieplik et al. (1995). Colourless crystals of polymorph (Ia) were grown by slow evaporation of a solution of the oily residue in an acetone–methanol mixture (1:4 v/v). Pale-yellow crystals of polymorph (Ib) were obtained via recrystallization of (Ia) from an acetone–methanol mixture (4:1 v/v).

Computing details top

For both compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 1998); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The molecule of polymorph (Ia), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dotted line indicates the intramolecular N—H···N hydrogen bond.
	Fig. 2. The molecule of polymorph (Ib), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dotted line indicates the intramolecular N—H···N hydrogen bond.
	Fig. 3. Part of the crystal structure of (Ia), showing the chain formed via the N—H···N hydrogen bonds. Dashed lines indicate intermolecular hydrogen bonds. [Symmetry code: (i) x − 1/2, y, −z + 1/2.]
	Fig. 4. Part of the crystal structure of (Ib), showing the chain formed via N—H···Cl hydrogen bonds. Dashed lines indicate intermolecular hydrogen bonds. [Symmetry code (ii) x, −y + 3/2, z + 1/2.]

(Ia) N-(4-chlorophenyl)-5-{[(4-chlorophenyl)amino]methyl}-6-methyl-2- phenylpyrimidin-4-amine top

Crystal data top

C₂₄H₂₀Cl₂N₄	D_x = 1.369 Mg m⁻³
M_r = 435.34	Melting point: 190 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 12344 reflections
a = 7.378 (3) Å	θ = 4.5–27.5°
b = 23.875 (6) Å	µ = 0.33 mm⁻¹
c = 23.984 (6) Å	T = 100 K
V = 4225 (2) Å³	Plate, colourless
Z = 8	0.50 × 0.15 × 0.05 mm
F(000) = 1808

Data collection top

Kuma KM4 CCD κ-geometry diffractometer	3240 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.075
Graphite monochromator	θ_max = 27.5°, θ_min = 4.5°
Detector resolution: 0 pixels mm^-1	h = −7→9
ω scans	k = −24→31
34892 measured reflections	l = −31→29
4829 independent reflections

Refinement top

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ²(F_o²) + (0.0597P)² where P = (F_o² + 2F_c²)/3
4829 reflections	(Δ/σ)_max < 0.001
278 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₄H₂₀Cl₂N₄	V = 4225 (2) Å³
M_r = 435.34	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.378 (3) Å	µ = 0.33 mm⁻¹
b = 23.875 (6) Å	T = 100 K
c = 23.984 (6) Å	0.50 × 0.15 × 0.05 mm

Data collection top

Kuma KM4 CCD κ-geometry diffractometer	3240 reflections with I > 2σ(I)
34892 measured reflections	R_int = 0.075
4829 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	0 restraints
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	Δρ_max = 0.58 e Å⁻³
4829 reflections	Δρ_min = −0.30 e Å⁻³
278 parameters

Special details top

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. Diffraction data for I were collected on a Xcalibur PX ω-geometry diffractometer equipped with an Oxford Cryosystems low-temperature device. The crystal structure was solved by direct methods using the SHELXS97 program (Sheldrick, 1990) and refined using SHELXL97 (Sheldrick, 1997). The full-matrix least-squares were completed, using anisotropic parameters for all non H-atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl4	0.20555 (11)	0.71671 (3)	0.36059 (3)	0.0266 (2)
Cl5	0.28914 (12)	0.28069 (4)	0.61868 (3)	0.0399 (3)
C61	0.5135 (4)	0.29693 (11)	0.24457 (12)	0.0242 (7)
H61A	0.5318	0.2846	0.2060	0.036*
H61B	0.4252	0.2723	0.2628	0.036*
H61C	0.6289	0.2953	0.2647	0.036*
C6	0.4434 (4)	0.35619 (11)	0.24487 (12)	0.0184 (6)
N1	0.4188 (3)	0.37939 (9)	0.19362 (9)	0.0198 (6)
C2	0.3554 (4)	0.43214 (11)	0.19285 (11)	0.0181 (6)
C21	0.3198 (4)	0.45829 (11)	0.13745 (12)	0.0191 (6)
C22	0.3602 (4)	0.43067 (12)	0.08810 (12)	0.0225 (7)
H22	0.4138	0.3945	0.0893	0.027*
C23	0.3233 (4)	0.45521 (13)	0.03712 (12)	0.0301 (8)
H23	0.3531	0.4360	0.0037	0.036*
C24	0.2433 (4)	0.50742 (14)	0.03453 (13)	0.0333 (8)
H24	0.2171	0.5241	−0.0005	0.040*
C25	0.2015 (4)	0.53532 (13)	0.08368 (13)	0.0322 (8)
H25	0.1460	0.5712	0.0823	0.039*
C26	0.2406 (4)	0.51102 (12)	0.13485 (12)	0.0250 (7)
H26	0.2130	0.5306	0.1683	0.030*
N3	0.3180 (3)	0.46380 (9)	0.23722 (9)	0.0186 (5)
C4	0.3440 (4)	0.44081 (11)	0.28706 (11)	0.0183 (6)
N4	0.3069 (3)	0.47235 (10)	0.33327 (10)	0.0212 (6)
H4	0.293 (4)	0.4552 (12)	0.3635 (13)	0.025*
C41	0.2765 (4)	0.53068 (11)	0.33572 (11)	0.0192 (6)
C42	0.3541 (4)	0.56818 (12)	0.29829 (12)	0.0243 (7)
H42	0.4231	0.5546	0.2677	0.029*
C43	0.3311 (4)	0.62540 (12)	0.30549 (12)	0.0263 (7)
H43	0.3849	0.6511	0.2801	0.032*
C44	0.2293 (4)	0.64472 (11)	0.34990 (11)	0.0202 (7)
C45	0.1504 (4)	0.60820 (12)	0.38682 (12)	0.0221 (7)
H45	0.0793	0.6220	0.4168	0.026*
C46	0.1753 (4)	0.55118 (12)	0.38001 (11)	0.0209 (7)
H46	0.1226	0.5258	0.4059	0.025*
C5	0.4077 (4)	0.38528 (11)	0.29363 (11)	0.0179 (6)
C57	0.4425 (4)	0.36231 (12)	0.35113 (11)	0.0215 (7)
H57A	0.4923	0.3239	0.3480	0.026*
H57B	0.5341	0.3859	0.3701	0.026*
N5	0.2776 (4)	0.36087 (10)	0.38460 (10)	0.0209 (6)
H5	0.187 (4)	0.3505 (13)	0.3662 (12)	0.025*
C51	0.2840 (4)	0.34056 (11)	0.43936 (11)	0.0189 (6)
C52	0.4367 (4)	0.34795 (12)	0.47281 (12)	0.0227 (7)
H52	0.5409	0.3659	0.4580	0.027*
C53	0.4378 (4)	0.32925 (12)	0.52777 (12)	0.0255 (7)
H53	0.5427	0.3341	0.5502	0.031*
C54	0.2867 (4)	0.30373 (12)	0.54934 (12)	0.0256 (7)
C55	0.1341 (4)	0.29545 (12)	0.51717 (12)	0.0247 (7)
H55	0.0305	0.2775	0.5324	0.030*
C56	0.1338 (4)	0.31362 (11)	0.46229 (12)	0.0224 (7)
H56	0.0294	0.3076	0.4399	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl4	0.0333 (5)	0.0167 (3)	0.0299 (4)	0.0014 (3)	0.0024 (4)	0.0000 (3)
Cl5	0.0367 (5)	0.0634 (6)	0.0194 (4)	0.0065 (5)	0.0023 (4)	0.0129 (4)
C61	0.0252 (17)	0.0197 (14)	0.0276 (17)	0.0006 (13)	0.0053 (14)	−0.0007 (13)
C6	0.0139 (16)	0.0172 (13)	0.0241 (16)	−0.0026 (12)	0.0025 (12)	0.0010 (13)
N1	0.0199 (14)	0.0196 (12)	0.0201 (13)	−0.0018 (11)	0.0044 (11)	0.0007 (10)
C2	0.0129 (15)	0.0216 (15)	0.0197 (15)	−0.0042 (13)	0.0021 (12)	−0.0001 (12)
C21	0.0147 (16)	0.0215 (15)	0.0213 (15)	−0.0028 (13)	−0.0006 (13)	0.0033 (12)
C22	0.0238 (18)	0.0221 (15)	0.0216 (16)	−0.0016 (14)	0.0015 (13)	0.0008 (13)
C23	0.035 (2)	0.0368 (19)	0.0184 (16)	−0.0079 (16)	0.0007 (14)	−0.0033 (14)
C24	0.037 (2)	0.0411 (19)	0.0217 (17)	−0.0039 (17)	−0.0049 (15)	0.0088 (15)
C25	0.032 (2)	0.0312 (17)	0.0332 (19)	0.0064 (16)	0.0012 (16)	0.0097 (15)
C26	0.0246 (18)	0.0296 (16)	0.0208 (16)	0.0039 (15)	0.0020 (13)	0.0002 (13)
N3	0.0207 (14)	0.0178 (12)	0.0172 (12)	−0.0019 (10)	0.0000 (11)	0.0000 (10)
C4	0.0154 (16)	0.0218 (15)	0.0178 (15)	−0.0046 (13)	0.0015 (12)	−0.0025 (12)
N4	0.0322 (15)	0.0179 (12)	0.0135 (12)	−0.0013 (11)	0.0023 (12)	0.0006 (10)
C41	0.0237 (17)	0.0178 (13)	0.0163 (14)	−0.0029 (13)	−0.0038 (13)	−0.0012 (11)
C42	0.0282 (18)	0.0229 (15)	0.0217 (16)	−0.0002 (14)	0.0046 (14)	−0.0030 (13)
C43	0.0332 (19)	0.0256 (16)	0.0200 (16)	−0.0058 (15)	0.0029 (14)	0.0044 (13)
C44	0.0244 (17)	0.0148 (13)	0.0214 (15)	−0.0007 (13)	−0.0042 (13)	−0.0011 (12)
C45	0.0233 (17)	0.0241 (15)	0.0188 (15)	−0.0010 (14)	0.0033 (13)	−0.0025 (12)
C46	0.0240 (18)	0.0216 (14)	0.0171 (15)	−0.0060 (14)	0.0007 (13)	0.0020 (12)
C5	0.0150 (15)	0.0186 (14)	0.0200 (15)	−0.0042 (12)	0.0018 (12)	0.0011 (12)
C57	0.0210 (17)	0.0203 (15)	0.0231 (16)	−0.0009 (13)	0.0004 (13)	0.0027 (12)
N5	0.0194 (14)	0.0254 (13)	0.0179 (13)	−0.0025 (12)	−0.0021 (11)	0.0032 (10)
C51	0.0255 (17)	0.0145 (13)	0.0167 (14)	0.0003 (14)	0.0002 (14)	−0.0006 (11)
C52	0.0248 (18)	0.0230 (16)	0.0204 (16)	0.0007 (14)	0.0032 (13)	0.0012 (13)
C53	0.0282 (19)	0.0279 (17)	0.0204 (16)	0.0041 (15)	−0.0025 (14)	−0.0014 (13)
C54	0.0342 (19)	0.0263 (15)	0.0163 (15)	0.0059 (15)	0.0028 (15)	0.0026 (13)
C55	0.0287 (18)	0.0206 (16)	0.0246 (16)	0.0031 (14)	0.0066 (14)	0.0005 (13)
C56	0.0279 (18)	0.0180 (15)	0.0214 (16)	0.0030 (14)	−0.0021 (13)	−0.0010 (12)

Geometric parameters (Å, º) top

Cl4—C44	1.746 (3)	C41—C46	1.388 (4)
Cl5—C54	1.752 (3)	C41—C42	1.391 (4)
C61—C6	1.506 (4)	C42—C43	1.387 (4)
C61—H61A	0.9800	C42—H42	0.9500
C61—H61B	0.9800	C43—C44	1.383 (4)
C61—H61C	0.9800	C43—H43	0.9500
C6—N1	1.360 (3)	C44—C45	1.372 (4)
C6—C5	1.385 (4)	C45—C46	1.383 (4)
N1—C2	1.344 (3)	C45—H45	0.9500
C2—N3	1.334 (3)	C46—H46	0.9500
C2—C21	1.491 (4)	C5—C57	1.506 (4)
C21—C22	1.387 (4)	C57—N5	1.458 (4)
C21—C26	1.390 (4)	C57—H57A	0.9900
C22—C23	1.383 (4)	C57—H57B	0.9900
C22—H22	0.9500	N5—C51	1.401 (3)
C23—C24	1.381 (4)	N5—H5	0.84 (3)
C23—H23	0.9500	C51—C56	1.394 (4)
C24—C25	1.389 (5)	C51—C52	1.394 (4)
C24—H24	0.9500	C52—C53	1.392 (4)
C25—C26	1.388 (4)	C52—H52	0.9500
C25—H25	0.9500	C53—C54	1.372 (4)
C26—H26	0.9500	C53—H53	0.9500
N3—C4	1.329 (3)	C54—C55	1.379 (4)
C4—N4	1.368 (3)	C55—C56	1.386 (4)
C4—C5	1.416 (4)	C55—H55	0.9500
N4—C41	1.412 (3)	C56—H56	0.9500
N4—H4	0.84 (3)

C6—C61—H61A	109.5	C41—C42—H42	119.9
C6—C61—H61B	109.5	C44—C43—C42	119.4 (3)
H61A—C61—H61B	109.5	C44—C43—H43	120.3
C6—C61—H61C	109.5	C42—C43—H43	120.3
H61A—C61—H61C	109.5	C45—C44—C43	121.0 (3)
H61B—C61—H61C	109.5	C45—C44—Cl4	119.2 (2)
N1—C6—C5	122.2 (2)	C43—C44—Cl4	119.7 (2)
N1—C6—C61	115.1 (2)	C44—C45—C46	119.5 (3)
C5—C6—C61	122.7 (3)	C44—C45—H45	120.2
C2—N1—C6	116.1 (2)	C46—C45—H45	120.2
N3—C2—N1	126.3 (3)	C45—C46—C41	120.6 (3)
N3—C2—C21	115.9 (2)	C45—C46—H46	119.7
N1—C2—C21	117.8 (2)	C41—C46—H46	119.7
C22—C21—C26	118.9 (3)	C6—C5—C4	116.0 (3)
C22—C21—C2	121.6 (2)	C6—C5—C57	123.9 (2)
C26—C21—C2	119.6 (3)	C4—C5—C57	120.0 (2)
C23—C22—C21	120.7 (3)	N5—C57—C5	111.7 (2)
C23—C22—H22	119.6	N5—C57—H57A	109.3
C21—C22—H22	119.6	C5—C57—H57A	109.3
C24—C23—C22	120.4 (3)	N5—C57—H57B	109.3
C24—C23—H23	119.8	C5—C57—H57B	109.3
C22—C23—H23	119.8	H57A—C57—H57B	107.9
C23—C24—C25	119.3 (3)	C51—N5—C57	119.8 (2)
C23—C24—H24	120.3	C51—N5—H5	115 (2)
C25—C24—H24	120.3	C57—N5—H5	112 (2)
C26—C25—C24	120.3 (3)	C56—C51—C52	118.3 (3)
C26—C25—H25	119.9	C56—C51—N5	120.2 (3)
C24—C25—H25	119.9	C52—C51—N5	121.5 (3)
C25—C26—C21	120.4 (3)	C53—C52—C51	120.6 (3)
C25—C26—H26	119.8	C53—C52—H52	119.7
C21—C26—H26	119.8	C51—C52—H52	119.7
C4—N3—C2	117.0 (2)	C54—C53—C52	119.7 (3)
N3—C4—N4	118.2 (2)	C54—C53—H53	120.2
N3—C4—C5	122.3 (2)	C52—C53—H53	120.2
N4—C4—C5	119.5 (3)	C53—C54—C55	121.1 (3)
C4—N4—C41	127.5 (2)	C53—C54—Cl5	119.3 (2)
C4—N4—H4	117 (2)	C55—C54—Cl5	119.7 (2)
C41—N4—H4	115 (2)	C54—C55—C56	119.2 (3)
C46—C41—C42	119.2 (3)	C54—C55—H55	120.4
C46—C41—N4	117.7 (2)	C56—C55—H55	120.4
C42—C41—N4	122.9 (3)	C55—C56—C51	121.2 (3)
C43—C42—C41	120.2 (3)	C55—C56—H56	119.4
C43—C42—H42	119.9	C51—C56—H56	119.4

C5—C6—N1—C2	−0.8 (4)	C43—C44—C45—C46	0.9 (4)
C61—C6—N1—C2	179.6 (2)	Cl4—C44—C45—C46	−177.2 (2)
C6—N1—C2—N3	1.4 (4)	C44—C45—C46—C41	−1.1 (4)
C6—N1—C2—C21	−177.7 (2)	C42—C41—C46—C45	0.4 (4)
N3—C2—C21—C22	177.2 (3)	N4—C41—C46—C45	175.8 (3)
N1—C2—C21—C22	−3.6 (4)	N1—C6—C5—C4	−0.1 (4)
N3—C2—C21—C26	−4.3 (4)	C61—C6—C5—C4	179.5 (3)
N1—C2—C21—C26	174.9 (3)	N1—C6—C5—C57	−176.6 (3)
C26—C21—C22—C23	0.3 (4)	C61—C6—C5—C57	3.0 (4)
C2—C21—C22—C23	178.8 (3)	N3—C4—C5—C6	0.6 (4)
C21—C22—C23—C24	−0.8 (5)	N4—C4—C5—C6	−179.5 (2)
C22—C23—C24—C25	0.5 (5)	N3—C4—C5—C57	177.3 (2)
C23—C24—C25—C26	0.3 (5)	N4—C4—C5—C57	−2.9 (4)
C24—C25—C26—C21	−0.8 (5)	C6—C5—C57—N5	−121.7 (3)
C22—C21—C26—C25	0.5 (4)	C4—C5—C57—N5	61.9 (3)
C2—C21—C26—C25	−178.1 (3)	C5—C57—N5—C51	179.8 (2)
N1—C2—N3—C4	−0.8 (4)	C57—N5—C51—C56	−148.8 (3)
C21—C2—N3—C4	178.2 (2)	C57—N5—C51—C52	33.1 (4)
C2—N3—C4—N4	179.9 (2)	C56—C51—C52—C53	−0.5 (4)
C2—N3—C4—C5	−0.2 (4)	N5—C51—C52—C53	177.6 (3)
N3—C4—N4—C41	−13.3 (4)	C51—C52—C53—C54	−0.6 (4)
C5—C4—N4—C41	166.9 (3)	C52—C53—C54—C55	1.0 (4)
C4—N4—C41—C46	155.5 (3)	C52—C53—C54—Cl5	−179.7 (2)
C4—N4—C41—C42	−29.3 (5)	C53—C54—C55—C56	−0.4 (4)
C46—C41—C42—C43	0.4 (4)	Cl5—C54—C55—C56	−179.7 (2)
N4—C41—C42—C43	−174.8 (3)	C54—C55—C56—C51	−0.7 (4)
C41—C42—C43—C44	−0.5 (4)	C52—C51—C56—C55	1.1 (4)
C42—C43—C44—C45	−0.1 (4)	N5—C51—C56—C55	−177.0 (3)
C42—C43—C44—Cl4	178.0 (2)

(Ib) N-(4-chlorophenyl)-5-{[(4-chlorophenyl)amino]methyl}-6-methyl-2- phenylpyrimidin-4-amine top

Crystal data top

C₂₄H₂₀Cl₂N₄	F(000) = 904
M_r = 435.34	D_x = 1.411 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 190 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.332 (4) Å	Cell parameters from 16673 reflections
b = 7.993 (2) Å	θ = 4.7–28.1°
c = 17.235 (4) Å	µ = 0.34 mm⁻¹
β = 104.06 (3)°	T = 100 K
V = 2048.9 (9) Å³	Plate, pale yellow
Z = 4	0.16 × 0.15 × 0.10 mm

Data collection top

Kuma KM4 CCD κ-geometry diffractometr	3895 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.043
Graphite monochromator	θ_max = 28.1°, θ_min = 4.7°
Detector resolution: 0 pixels mm^-1	h = −20→20
ω scans	k = −8→10
26386 measured reflections	l = −22→22
4952 independent reflections

Refinement top

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.0769P)² + 0.4721P] where P = (F_o² + 2F_c²)/3
4952 reflections	(Δ/σ)_max = 0.001
278 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₄H₂₀Cl₂N₄	V = 2048.9 (9) Å³
M_r = 435.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.332 (4) Å	µ = 0.34 mm⁻¹
b = 7.993 (2) Å	T = 100 K
c = 17.235 (4) Å	0.16 × 0.15 × 0.10 mm
β = 104.06 (3)°

Data collection top

Kuma KM4 CCD κ-geometry diffractometr	3895 reflections with I > 2σ(I)
26386 measured reflections	R_int = 0.043
4952 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.49 e Å⁻³
4952 reflections	Δρ_min = −0.30 e Å⁻³
278 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl4	0.66123 (4)	0.33111 (7)	0.37837 (3)	0.02978 (17)
Cl5	0.33415 (4)	0.49845 (8)	0.89159 (4)	0.03679 (18)
N1	0.88258 (12)	0.3531 (2)	0.91081 (10)	0.0211 (4)
C2	0.86547 (13)	0.2882 (3)	0.83714 (12)	0.0186 (4)
C21	0.90082 (13)	0.1179 (3)	0.82712 (12)	0.0189 (4)
C22	0.95206 (14)	0.0301 (3)	0.89212 (13)	0.0247 (5)
H22	0.9675	0.0811	0.9434	0.030*
C23	0.98096 (15)	−0.1325 (3)	0.88235 (14)	0.0276 (5)
H23	1.0151	−0.1922	0.9272	0.033*
C24	0.96003 (15)	−0.2073 (3)	0.80745 (15)	0.0270 (5)
H24	0.9801	−0.3177	0.8009	0.032*
C25	0.90980 (16)	−0.1202 (3)	0.74239 (14)	0.0266 (5)
H25	0.8957	−0.1711	0.6910	0.032*
C26	0.87980 (15)	0.0411 (3)	0.75156 (13)	0.0230 (5)
H26	0.8450	0.0994	0.7066	0.028*
N3	0.81732 (12)	0.3611 (2)	0.77059 (10)	0.0194 (4)
C4	0.78123 (14)	0.5096 (2)	0.77805 (12)	0.0187 (4)
N4	0.73384 (12)	0.5890 (2)	0.70989 (10)	0.0215 (4)
H4	0.7017 (17)	0.676 (3)	0.7178 (15)	0.026*
C41	0.72011 (14)	0.5287 (3)	0.63102 (12)	0.0206 (4)
C42	0.78666 (15)	0.4462 (3)	0.60340 (13)	0.0232 (5)
H42	0.8444	0.4303	0.6382	0.028*
C43	0.76924 (15)	0.3872 (3)	0.52539 (13)	0.0245 (5)
H43	0.8144	0.3296	0.5068	0.029*
C44	0.68490 (15)	0.4135 (3)	0.47504 (12)	0.0226 (5)
C45	0.61949 (15)	0.5026 (3)	0.50023 (13)	0.0250 (5)
H45	0.5629	0.5240	0.4644	0.030*
C46	0.63733 (15)	0.5600 (3)	0.57807 (13)	0.0233 (5)
H46	0.5927	0.6215	0.5957	0.028*
C5	0.78988 (14)	0.5870 (3)	0.85380 (12)	0.0201 (4)
C57	0.74856 (15)	0.7570 (3)	0.86288 (13)	0.0239 (5)
H57A	0.7455	0.7706	0.9192	0.029*
H57B	0.7889	0.8453	0.8512	0.029*
N5	0.65831 (13)	0.7829 (2)	0.81104 (11)	0.0244 (4)
H5	0.6506 (17)	0.890 (3)	0.7994 (15)	0.029*
C51	0.58325 (15)	0.7165 (3)	0.83278 (12)	0.0217 (4)
C52	0.58972 (14)	0.5813 (3)	0.88475 (13)	0.0224 (4)
H52	0.6470	0.5346	0.9083	0.027*
C53	0.51332 (15)	0.5139 (3)	0.90247 (13)	0.0237 (5)
H53	0.5183	0.4210	0.9376	0.028*
C54	0.42980 (15)	0.5828 (3)	0.86870 (13)	0.0258 (5)
C55	0.42173 (16)	0.7183 (3)	0.81736 (13)	0.0270 (5)
H55	0.3643	0.7655	0.7948	0.032*
C56	0.49781 (16)	0.7847 (3)	0.79899 (13)	0.0261 (5)
H56	0.4922	0.8769	0.7633	0.031*
C6	0.84411 (14)	0.5028 (3)	0.91826 (13)	0.0209 (4)
C61	0.86469 (16)	0.5710 (3)	1.00255 (13)	0.0288 (5)
H61A	0.9119	0.5032	1.0370	0.043*
H61B	0.8103	0.5669	1.0228	0.043*
H61C	0.8853	0.6871	1.0025	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl4	0.0434 (4)	0.0247 (3)	0.0194 (3)	−0.0037 (2)	0.0041 (2)	−0.0016 (2)
Cl5	0.0213 (3)	0.0443 (4)	0.0447 (4)	−0.0003 (2)	0.0078 (3)	−0.0010 (3)
N1	0.0212 (9)	0.0237 (9)	0.0178 (9)	−0.0022 (7)	0.0034 (7)	0.0006 (7)
C2	0.0169 (10)	0.0205 (10)	0.0196 (10)	−0.0035 (8)	0.0066 (8)	0.0012 (8)
C21	0.0160 (10)	0.0189 (10)	0.0225 (10)	−0.0019 (8)	0.0058 (8)	0.0023 (8)
C22	0.0202 (11)	0.0289 (11)	0.0233 (11)	−0.0001 (9)	0.0018 (9)	0.0021 (9)
C23	0.0199 (11)	0.0282 (12)	0.0341 (13)	0.0031 (9)	0.0051 (9)	0.0065 (10)
C24	0.0227 (11)	0.0206 (11)	0.0410 (13)	0.0028 (9)	0.0142 (10)	0.0022 (10)
C25	0.0307 (12)	0.0237 (11)	0.0283 (12)	−0.0031 (9)	0.0127 (10)	−0.0040 (9)
C26	0.0237 (11)	0.0239 (11)	0.0220 (11)	0.0003 (9)	0.0066 (9)	0.0032 (9)
N3	0.0208 (9)	0.0198 (9)	0.0176 (8)	−0.0005 (7)	0.0047 (7)	0.0008 (7)
C4	0.0181 (10)	0.0198 (10)	0.0188 (10)	−0.0025 (8)	0.0055 (8)	0.0009 (8)
N4	0.0251 (10)	0.0211 (9)	0.0180 (9)	0.0050 (8)	0.0050 (7)	−0.0005 (7)
C41	0.0247 (11)	0.0204 (10)	0.0174 (10)	0.0005 (8)	0.0065 (8)	0.0026 (8)
C42	0.0218 (11)	0.0269 (11)	0.0206 (10)	0.0048 (9)	0.0044 (9)	0.0040 (9)
C43	0.0295 (12)	0.0236 (11)	0.0220 (11)	0.0048 (9)	0.0094 (9)	0.0027 (9)
C44	0.0321 (12)	0.0197 (10)	0.0158 (10)	−0.0038 (9)	0.0055 (9)	0.0025 (8)
C45	0.0220 (11)	0.0298 (12)	0.0209 (11)	−0.0006 (9)	0.0010 (9)	0.0050 (9)
C46	0.0223 (11)	0.0255 (11)	0.0225 (11)	0.0042 (9)	0.0063 (9)	0.0037 (9)
C5	0.0201 (10)	0.0203 (10)	0.0212 (10)	−0.0042 (8)	0.0077 (8)	−0.0013 (8)
C57	0.0263 (11)	0.0216 (10)	0.0248 (11)	−0.0047 (9)	0.0083 (9)	−0.0036 (9)
N5	0.0304 (10)	0.0183 (9)	0.0261 (10)	0.0043 (8)	0.0102 (8)	0.0029 (8)
C51	0.0278 (11)	0.0212 (10)	0.0170 (10)	0.0028 (9)	0.0072 (9)	−0.0059 (8)
C52	0.0208 (11)	0.0225 (10)	0.0228 (11)	0.0050 (9)	0.0032 (9)	−0.0033 (9)
C53	0.0250 (11)	0.0235 (11)	0.0221 (11)	0.0017 (9)	0.0048 (9)	0.0008 (9)
C54	0.0219 (11)	0.0286 (12)	0.0267 (11)	−0.0003 (9)	0.0058 (9)	−0.0081 (9)
C55	0.0258 (12)	0.0326 (12)	0.0196 (10)	0.0103 (10)	0.0000 (9)	−0.0057 (9)
C56	0.0334 (13)	0.0261 (11)	0.0180 (10)	0.0083 (10)	0.0045 (9)	−0.0025 (9)
C6	0.0219 (11)	0.0233 (10)	0.0185 (10)	−0.0072 (8)	0.0073 (8)	−0.0029 (8)
C61	0.0358 (13)	0.0321 (12)	0.0171 (11)	−0.0020 (10)	0.0039 (9)	−0.0039 (9)

Geometric parameters (Å, º) top

Cl4—C44	1.746 (2)	C43—H43	0.9500
Cl5—C54	1.744 (2)	C44—C45	1.383 (3)
N1—C2	1.337 (3)	C45—C46	1.381 (3)
N1—C6	1.353 (3)	C45—H45	0.9500
C2—N3	1.337 (3)	C46—H46	0.9500
C2—C21	1.491 (3)	C5—C6	1.389 (3)
C21—C22	1.392 (3)	C5—C57	1.524 (3)
C21—C26	1.405 (3)	C57—N5	1.468 (3)
C22—C23	1.397 (3)	C57—H57A	0.9900
C22—H22	0.9500	C57—H57B	0.9900
C23—C24	1.388 (3)	N5—C51	1.399 (3)
C23—H23	0.9500	N5—H5	0.88 (3)
C24—C25	1.384 (3)	C51—C52	1.392 (3)
C24—H24	0.9500	C51—C56	1.408 (3)
C25—C26	1.391 (3)	C52—C53	1.389 (3)
C25—H25	0.9500	C52—H52	0.9500
C26—H26	0.9500	C53—C54	1.386 (3)
N3—C4	1.329 (3)	C53—H53	0.9500
C4—N4	1.377 (3)	C54—C55	1.385 (3)
C4—C5	1.421 (3)	C55—C56	1.386 (3)
N4—C41	1.409 (3)	C55—H55	0.9500
N4—H4	0.88 (3)	C56—H56	0.9500
C41—C42	1.392 (3)	C6—C61	1.511 (3)
C41—C46	1.394 (3)	C61—H61A	0.9800
C42—C43	1.388 (3)	C61—H61B	0.9800
C42—H42	0.9500	C61—H61C	0.9800
C43—C44	1.387 (3)

C2—N1—C6	116.32 (18)	C44—C45—H45	120.4
N1—C2—N3	125.84 (19)	C45—C46—C41	120.7 (2)
N1—C2—C21	118.12 (18)	C45—C46—H46	119.7
N3—C2—C21	116.03 (18)	C41—C46—H46	119.7
C22—C21—C26	118.9 (2)	C6—C5—C4	115.33 (19)
C22—C21—C2	121.16 (19)	C6—C5—C57	122.22 (19)
C26—C21—C2	119.93 (19)	C4—C5—C57	122.29 (19)
C21—C22—C23	120.4 (2)	N5—C57—C5	114.66 (17)
C21—C22—H22	119.8	N5—C57—H57A	108.6
C23—C22—H22	119.8	C5—C57—H57A	108.6
C24—C23—C22	120.3 (2)	N5—C57—H57B	108.6
C24—C23—H23	119.8	C5—C57—H57B	108.6
C22—C23—H23	119.8	H57A—C57—H57B	107.6
C25—C24—C23	119.6 (2)	C51—N5—C57	119.91 (18)
C25—C24—H24	120.2	C51—N5—H5	110.9 (17)
C23—C24—H24	120.2	C57—N5—H5	109.3 (17)
C24—C25—C26	120.6 (2)	C52—C51—N5	122.18 (19)
C24—C25—H25	119.7	C52—C51—C56	118.7 (2)
C26—C25—H25	119.7	N5—C51—C56	119.1 (2)
C25—C26—C21	120.2 (2)	C53—C52—C51	120.7 (2)
C25—C26—H26	119.9	C53—C52—H52	119.6
C21—C26—H26	119.9	C51—C52—H52	119.6
C4—N3—C2	117.52 (18)	C54—C53—C52	119.8 (2)
N3—C4—N4	118.35 (19)	C54—C53—H53	120.1
N3—C4—C5	121.96 (19)	C52—C53—H53	120.1
N4—C4—C5	119.69 (18)	C55—C54—C53	120.6 (2)
C4—N4—C41	126.11 (18)	C55—C54—Cl5	119.83 (18)
C4—N4—H4	115.5 (16)	C53—C54—Cl5	119.57 (18)
C41—N4—H4	117.5 (16)	C54—C55—C56	119.7 (2)
C42—C41—C46	119.17 (19)	C54—C55—H55	120.1
C42—C41—N4	122.80 (19)	C56—C55—H55	120.1
C46—C41—N4	117.97 (19)	C55—C56—C51	120.5 (2)
C43—C42—C41	120.5 (2)	C55—C56—H56	119.8
C43—C42—H42	119.7	C51—C56—H56	119.8
C41—C42—H42	119.7	N1—C6—C5	122.84 (19)
C44—C43—C42	119.0 (2)	N1—C6—C61	114.58 (19)
C44—C43—H43	120.5	C5—C6—C61	122.6 (2)
C42—C43—H43	120.5	C6—C61—H61A	109.5
C45—C44—C43	121.2 (2)	C6—C61—H61B	109.5
C45—C44—Cl4	119.70 (17)	H61A—C61—H61B	109.5
C43—C44—Cl4	119.07 (17)	C6—C61—H61C	109.5
C46—C45—C44	119.2 (2)	H61A—C61—H61C	109.5
C46—C45—H45	120.4	H61B—C61—H61C	109.5

C6—N1—C2—N3	3.0 (3)	C44—C45—C46—C41	−0.1 (3)
C6—N1—C2—C21	−175.53 (17)	C42—C41—C46—C45	3.4 (3)
N1—C2—C21—C22	−1.5 (3)	N4—C41—C46—C45	−179.33 (19)
N3—C2—C21—C22	179.81 (19)	N3—C4—C5—C6	4.7 (3)
N1—C2—C21—C26	176.16 (19)	N4—C4—C5—C6	−175.66 (18)
N3—C2—C21—C26	−2.5 (3)	N3—C4—C5—C57	−179.88 (19)
C26—C21—C22—C23	−0.8 (3)	N4—C4—C5—C57	−0.2 (3)
C2—C21—C22—C23	176.88 (19)	C6—C5—C57—N5	−144.4 (2)
C21—C22—C23—C24	1.0 (3)	C4—C5—C57—N5	40.5 (3)
C22—C23—C24—C25	−0.4 (3)	C5—C57—N5—C51	80.5 (2)
C23—C24—C25—C26	−0.3 (3)	C57—N5—C51—C52	−22.9 (3)
C24—C25—C26—C21	0.5 (3)	C57—N5—C51—C56	159.35 (19)
C22—C21—C26—C25	0.1 (3)	N5—C51—C52—C53	−177.28 (19)
C2—C21—C26—C25	−177.63 (19)	C56—C51—C52—C53	0.5 (3)
N1—C2—N3—C4	−1.7 (3)	C51—C52—C53—C54	−0.6 (3)
C21—C2—N3—C4	176.86 (17)	C52—C53—C54—C55	0.0 (3)
C2—N3—C4—N4	177.95 (18)	C52—C53—C54—Cl5	−179.65 (16)
C2—N3—C4—C5	−2.4 (3)	C53—C54—C55—C56	0.6 (3)
N3—C4—N4—C41	−0.8 (3)	Cl5—C54—C55—C56	−179.74 (16)
C5—C4—N4—C41	179.56 (19)	C54—C55—C56—C51	−0.6 (3)
C4—N4—C41—C42	−39.4 (3)	C52—C51—C56—C55	0.1 (3)
C4—N4—C41—C46	143.4 (2)	N5—C51—C56—C55	177.96 (19)
C46—C41—C42—C43	−3.7 (3)	C2—N1—C6—C5	−0.2 (3)
N4—C41—C42—C43	179.1 (2)	C2—N1—C6—C61	179.62 (18)
C41—C42—C43—C44	0.9 (3)	C4—C5—C6—N1	−3.3 (3)
C42—C43—C44—C45	2.5 (3)	C57—C5—C6—N1	−178.75 (19)
C42—C43—C44—Cl4	−177.11 (16)	C4—C5—C6—C61	176.85 (19)
C43—C44—C45—C46	−2.8 (3)	C57—C5—C6—C61	1.4 (3)
Cl4—C44—C45—C46	176.75 (17)

Experimental details

	(Ia)	(Ib)
Crystal data
Chemical formula	C₂₄H₂₀Cl₂N₄	C₂₄H₂₀Cl₂N₄
M_r	435.34	435.34
Crystal system, space group	Orthorhombic, Pbca	Monoclinic, P2₁/c
Temperature (K)	100	100
a, b, c (Å)	7.378 (3), 23.875 (6), 23.984 (6)	15.332 (4), 7.993 (2), 17.235 (4)
α, β, γ (°)	90, 90, 90	90, 104.06 (3), 90
V (Å³)	4225 (2)	2048.9 (9)
Z	8	4
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.33	0.34
Crystal size (mm)	0.50 × 0.15 × 0.05	0.16 × 0.15 × 0.10

Data collection
Diffractometer	Kuma KM4 CCD κ-geometry diffractometer	Kuma KM4 CCD κ-geometry diffractometr
Absorption correction	–	–
No. of measured, independent and observed [I > 2σ(I)] reflections	34892, 4829, 3240	26386, 4952, 3895
R_int	0.075	0.043
(sin θ/λ)_max (Å⁻¹)	0.650	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.148, 1.15	0.057, 0.145, 1.12
No. of reflections	4829	4952
No. of parameters	278	278
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.30	0.49, −0.30

Computer programs: CrysAlis CCD (Oxford Diffraction, 2003), CrysAlis RED (Oxford Diffraction, 2003), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Bruker, 1998), SHELXL97.

Comparison of bond lengths and torsion angles for polymorphs (Ia) and (Ib) (Å, °) top

Parameter	(Ia)	(Ib)
N1-C2	1.344 (3)	1.337 (2)
C2-N3	1.334 (3)	1.337 (3)
N3-C4	1.329 (3)	1.329 (3)
C4-C5	1.416 (4)	1.421 (3)
C5-C6	1.385 (4)	1.389 (3)
C6-N1	1.360 (3)	1.353 (3)
C4-N4	1.368 (3)	1.377 (3)
N4-C41	1.412 (3)	1.409 (3)
C5-C57	1.506 (4)	1.524 (3)
C57-N5	1.458 (4)	1.468 (3)
N5-C51	1.401 (3)	1.399 (3)
N1-C2-C21-C22	-3.6 (4)	-1.5 (3)
N3-C4-N4-C41	-13.3 (4)	-0.8 (3)
C5-C4-N4-C41	166.9 (3)	179.6 (2)
C4-N4-C41-C42	-29.3 (5)	-39.4 (3)
C4-C5-C57-N5	61.9 (3)	40.5 (3)
C6-C5-C57-N5	-121.7 (3)	-144.4 (2)
C5-C57-N5-C51	179.8 (2)	80.5 (2)
C57-N5-C51-C52	33.1 (4)	-22.9 (3)
C57-N5-C51-C56	-148.8 (3)	159.4 (2)

Hydrogen-bonding geometry for polymorphs (Ia) and (Ib) (Å, °) top

	D-H···A	D-H	H···A	D···A	D-H···A
(Ia)	N4-H4···N5	0.84 (3)	2.31 (3)	2.940 (3)	132 (3)
	N5-H5···N1ⁱ	0.84 (3)	2.54 (3)	3.274 (4)	147 (3)
(Ib)	N4-H4···N5	0.88 (3)	2.07 (3)	2.786 (3)	138 (2)
	N5-H5···Cl4ⁱⁱ	0.88 (3)	2.60 (3)	3.292 (2)	137 (2)

Symmetry codes: (i) x − 1/2, y, 1/2 − z; (ii) x, −y + 3/2, z + 1/2.

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Two polymorphic forms of N-(4-chloro­phenyl)-5-[(4-chlorophenyl)aminomethyl]-6-methyl-2-phenyl­pyrimidin-4-amine

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Two polymorphic forms of N-(4-chlorophenyl)-5-[(4-chlorophenyl)aminomethyl]-6-methyl-2-phenylpyrimidin-4-amine