organic compounds
5-[(3,5-Dichloroanilino)methyl]-N-(3,5-dichlorophenyl)-6-methyl-2-phenylpyrimidin-4-amine
aDepartment of Organic Chemistry, Wrocław Medical University, 9 Grodzka St, 50-137 Wrocław, Poland, bDepartment of Applied Pharmacy, Wrocław Medical Uniwersity, 38 Szewska St, 50-137 Wrocław, Poland, cDepartment of Bioorganic Chemistry, Faculty of Engineering and Economics, Wrocław University of Economics, 118/120 Komandorska St, 53-345 Wrocław, Poland, and dFaculty of Chemistry, University of Wrocław, 14 Joliot-Curie St, 50-383 Wrocław, Poland
*Correspondence e-mail: isai@o2.pl
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 molecular conformation is stabilized by an intramolecular N—H⋯N hydrogen bond closing a six-membered ring with an S(6) motif. In the crystal, a pair of intermolecular N—H⋯N hydrogen bonds connect two molecules, forming inversion dimers with R22(12) motifs. C—H⋯π interactions links the dimers into a chain running along the a-axis direction. There are also π–π stacking interactions [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
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Data collection
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Refinement
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Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell 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.
Supporting information
10.1107/S160053681204665X/is5217sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681204665X/is5217Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681204665X/is5217Isup3.cml
The title compound was obtained by adopting the procedure described previously by Cieplik et al. (2003). 4 g (0.010 mmol) of 4-(3,5-dichlorophenyl)amine-5-chloromethyl-2-phenyl-6-methylpyrimidine was dissolved in 50 ml of chloroform, and 2 g of 3,5-dichloroaniline. The reaction mixture was refluxed for 7 h with vigorous stirring, then was cooled and poured into 100 ml of water. The aqueous solution was extracted three times with chloroform (50 ml). The combined chloroform phases were dried over MgSO4, filtered and concentrated under vacuum. The oily residue was purified by
on silica gel (200–400 mesh) using CHCl3 as the and by crystallization from methanol to give single crystals (yield: 4.37 g, 82.1%, m.p. 380–382 K).The N-bonded H atoms were found from difference Fourier maps and refined with Uiso(H) = 1.2Ueq(N). The remaining H atoms were treated as riding on their carrier atoms, with C—H distances in the range 0.95–0.99 Å, and refined with Uiso(H) = 1.2Ueq(C), except methyl groups where Uiso(H) = 1.5Ueq(C).
Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell
CrysAlis CCD (Oxford Diffraction, 2007); 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 (Sheldrick, 2008).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 |
C24H18Cl4N4 | γ = 81.42 (5)° |
Mr = 504.22 | V = 1130.4 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.267 (3) Å | Mo Kα radiation |
b = 11.271 (4) Å | µ = 0.54 mm−1 |
c = 12.788 (4) Å | T = 85 K |
α = 76.53 (5)° | 0.23 × 0.14 × 0.08 mm |
β = 78.95 (5)° |
Oxford Xcalibur PX with Onyx CCD diffractometer | 5082 reflections with I > 2σ(I) |
19215 measured reflections | Rint = 0.041 |
8041 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.75 e Å−3 |
8041 reflections | Δρmin = −0.41 e Å−3 |
296 parameters |
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) |
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) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C24H18Cl4N4 |
Mr | 504.22 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 85 |
a, b, c (Å) | 8.267 (3), 11.271 (4), 12.788 (4) |
α, β, γ (°) | 76.53 (5), 78.95 (5), 81.42 (5) |
V (Å3) | 1130.4 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.54 |
Crystal size (mm) | 0.23 × 0.14 × 0.08 |
Data collection | |
Diffractometer | Oxford Xcalibur PX with Onyx CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19215, 8041, 5082 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.757 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.100, 1.03 |
No. of reflections | 8041 |
No. of parameters | 296 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.75, −0.41 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).
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) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1. |
References
Cieplik, J., Pluta, J., Bryndal, I. & Lis, T. (2006). Acta Cryst. C62, o259–o261. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Cieplik, J., Pluta, J. & Gubrynowicz, O. (2003). Boll. Chim. Farm. 142, 146–150. PubMed CAS Google Scholar
Cieplik, J., Raginia, M., Pluta, J., Gubrynowicz, O., Bryndal, I. & Lis, T. (2008). Acta Pol. Pharm. Drug Res. 65, 427–434. CAS Google Scholar
Cieplik, J., Stolarczyk, M., Bryndal, I. & Lis, T. (2012). Acta Cryst. E68, o1729–o1730. CSD CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
In this work, we extend the earlier analysis of 6-methyl-2-phenyl-5-substituted pyrimidine derivatives (Cieplik et al., 2003, 2008, 2012) and report the crystal strucure of this class of derivatives, namely 5-[(3,5-dichloroanilino)methyl]-N-(3,5-dichlorophenyl)-6-methyl-2-phenylpyrimidin-4-amine.
The title compound crystallizes in P1 space group, with one molecule in the asymmetric unit (Fig. 1). There is an intramolecular N—H···N hydrogen bond between N4—H4 and N5 (Table 1), which closes six-memebered ring. This S(6) motif was observed in earlier described similar compounds (Cieplik et al., 2006). The conformation of the title molecule is best defined by dihedral angles formed between the pyrimidine ring plane and the planes of the phenyl ring attached to the atom C2 and two other aryl rings of the (3,5-dichlorophenyl)amino or the (3,5-dichlorophenyl)aminomethyl groups attached, respectively, to the atoms C4 or C5 of the pyrimidine ring. These dihedral angles are 19.1 (2), 4.1 (2) and 67.5 (2)°, respectively.
The molecules are linked by a combination of N—H···N, C—H···π (Table 1) and also aromatic π–π stacking interactions. The N5 amine atom acts as hydrogen-bond donor to the pyrimidine atom N1 of adjacent molecule at (-x + 1, -y + 1, -z + 1). This result in the formation of a dimer via a cyclic R22(12) ring motif. Additionally, the C57—H572 groups acts as a donor of C—H···π(arene) interaction to the benzene C21—C26 ring (-x, -y + 1, -z + 1). The combination of N—H···N and C—H···π interactions generates a chain running along the [100] direction (Fig. 2). Between C41—C46 rings of molecules of adjacent chains related by translation along a direction, there is also an aromatic π–π stacking interaction. The distance between the ring centroids of molecules at (x, y, z) and (-x, -y + 2, -z + 1) is 3.666 (4) Å with an interplanar spacing of 3.486 (4) Å and a centroid offset of 1.13 Å.