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2-[(4-Chlorobenzyl)sulfanyl]-4-(2-methylpropyl)-6-[3-(trifluoromethyl)anilino]pyrimidine-5-carbonitrile
aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: Edward.Tiekink@gmail.com
Three independent molecules comprise the 23H20ClF3N4S. The conformations of the molecules are similar with the chlorobenzene and CF3-benzene rings almost perpendicular to, and almost co-planar with, the pyrimidinyl ring [range of dihedral angles = 80.36 (13)–88.07 (14) and 11.89 (14)–23.30 (14)°, respectively]; the benzene rings are roughly orthogonal to each other [64.81 (16)–72.16 (15)°]. In the crystal, two of the independent molecules associate via weak N—H⋯N(cyano) hydrogen bonds and 12-membered {⋯HNC3N}2 synthons; the third independent molecule self-associates similarly but about a centre of inversion. The sample studied was found to be a non-merohedral twin and the minor twin component refined to 47.16 (7)%.
of the title compound, CRelated literature
For the chemotherapeutic efficacy of pyrimidine derivatives, see: Al-Safarjalani et al. (2005); Brunelle et al. (2007
); Ding et al. (2006
); Al-Abdullah et al. (2011
). For recent interest in the chemical and pharmacological properties of pyrimidine derivatives, see: Al-Omar et al. (2010
); El-Emam et al. (2011
). For the treatment of data from a twinned crystal, see: Spek (2009
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: ORTEP-3 (Farrugia, 1997
), DIAMOND (Brandenburg, 2006
) and QMol (Gans & Shalloway, 2001
); software used to prepare material for publication: publCIF (Westrip, 2010
).
Supporting information
https://doi.org/10.1107/S1600536812025895/hb6786sup1.cif
contains datablocks general, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025895/hb6786Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812025895/hb6786Isup3.cml
To a solution of 2-(4-chlorobenzylsulfanyl)-6-chloro-4-(2-methylpropyl)pyrimidine-5-carbonitrile (705 mg, 2 mmol) in ethanol (8 ml), 3-trifluoromethylaniline (0.002 mol) and anhydrous potassium carbonate (322 mg, 2 mmol) were added and the mixture was heated under reflux for 6 h. On cooling the mixture, the solvent was then distilled in vacuo, and water (10 ml) was added to the residue. The separated precipitate was filtered, washed with cold water, dried and crystallized from ethanol to yield 591 mg (62%) of the title compound as colourless crystals. M.pt: 409–411 K. Colourless prisms were obtained by slow evaporation of its CHCl3:EtOH (1:1, 5 ml) solution held at room temperature. 1H NMR (DMSO-d6, 500.13 MHz): δ 0.92 (d, 6H, CH3, J = 7.0 Hz), 2.08–2.12 (m, 1H, CH), 2.62 (d, 2H, CH2CH, J = 7.0 Hz), 4.24 (s, 2H, CH2S), 7.10–7.25 (m, 4H, Ar—H), 7.45–7.57 (m, 2H, Ar—H), 7.83–7.85 (m, 1H, Ar—H), 8.0 (s, 1H, Ar—H), 10.01 (s, 1H, NH). 13C NMR (DMSO-d6, 125.76 MHz): δ 21.88 (CH3CH), 27.68 (CHCH3), 33.06 (CH2S), 44.92 (CH2CH), 87.66 (C-5), 115.02 (CN), 115.65, 121.23, 124.08, 127.23, 128.65, 129.60, 129.75, 129.90, 131.25, 131.86, 137.23, 139.26 (Ar—C & CF3), 158.90 (C-6), 172.88, 173.28 (C-2 & C-4).
Carbon-bound H-atoms were placed in calculated positions [N—H = 0.88 Å and C—H = 0.95 to 1.00 Å, Uiso(H) = 1.2–1.5Ueq(N, C)] and were included in the 11 8 2) and (0 2 4), were omitted owing to poor agreement. The maximum and minimum residual electron density peaks of 1.44 and 0.53 e Å-3, respectively, were located 0.51 Å and 0.81 Å from the H13C and F9 atoms, respectively.
in the riding model approximation. The sample studied iss a non-merohedral twin and a full sphere of reflections was measured. As it was not possible to separate the diffraction spots in two domains, the twin domains were separated using the TwinRotMat routine of PLATON (Spek, 2009). The minor twin component refined to 47.16 (7)%. Two reflections,i.e. (The chemotherapeutic efficacy of pyrimidine derivatives is related to their ability to inhibit vital enzymes responsible for DNA bio-synthesis. Thus, several pyrimidine non-nucleoside derivatives are known to exhibit anti-cancer (Al-Safarjalani et al., 2005), anti-viral (Brunelle et al., 2007; Ding et al., 2006) and anti-bacterial activities (Al-Abdullah et al., 2011). In continuation to our interest in the chemical and pharmacological properties of pyrimidine derivatives (Al-Omar et al., 2010; El-Emam et al. 2011), we synthesized the title compound (I) as potential a chemotherapeutic agent.
In (I), Fig. 1, three independent molecules comprise the
and these have very similar molecular conformations as seen in the overlay diagram, Fig. 2. With respect to the pyrimidinyl ring, the chlorobenzene and CF3-benzene rings form dihedral angles of 80.36 (13) and 11.89 (14)°, respectively, for the N1-containing molecule; the dihedral angle between the benzene rings is 69.50 (14)°. For the N5-containing molecule the dihedral angles are 88.07 (14), 23.30 (14) and 64.81 (16), respectively, and for the N9-containing molecule, the angles are 85.94 (14), 13.81 (14) and 72.16 (15)°, respectively. In each case, the 2-methylpropyl group is orientated in the same direction as the chlorobenzene ring.In the
the N1- and N5-containing molecules associate to form a two molecule aggregate via N—H···N(cyano) hydrogen bonds and 12-membered {···HNC3N}2 synthons, Table 1 and Fig. 3. The N3-containing molecules self-associate similarly but over a centre of inversion, Table 1.For the chemotherapeutic efficacy of pyrimidine derivatives, see: Al-Safarjalani et al. (2005); Brunelle et al. (2007); Ding et al. (2006); Al-Abdullah et al. (2011). For recent interest in the chemical and pharmacological properties of pyrimidine derivatives, see: Al-Omar et al. (2010); El-Emam et al. (2011). For the treatment of data from a twinned crystal, see: Spek (2009).
Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and QMol (Gans & Shalloway, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).C23H20ClF3N4S | Z = 6 |
Mr = 476.94 | F(000) = 1476 |
Triclinic, P1 | Dx = 1.449 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54184 Å |
a = 15.3906 (6) Å | Cell parameters from 6525 reflections |
b = 15.7040 (7) Å | θ = 2.9–76.4° |
c = 15.9129 (7) Å | µ = 2.83 mm−1 |
α = 89.568 (3)° | T = 100 K |
β = 74.825 (4)° | Prism, colourless |
γ = 62.980 (4)° | 0.35 × 0.15 × 0.03 mm |
V = 3278.9 (2) Å3 |
Agilent SuperNova Dual diffractometer with Atlas detector | 25266 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 18393 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.075 |
Detector resolution: 10.4041 pixels mm-1 | θmax = 77.2°, θmin = 2.9° |
ω scan | h = −19→14 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −19→19 |
Tmin = 0.437, Tmax = 0.920 | l = −20→20 |
38203 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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.190 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.1074P)2 + 1.9445P] where P = (Fo2 + 2Fc2)/3 |
25266 reflections | (Δ/σ)max = 0.001 |
866 parameters | Δρmax = 1.44 e Å−3 |
0 restraints | Δρmin = −0.53 e Å−3 |
C23H20ClF3N4S | γ = 62.980 (4)° |
Mr = 476.94 | V = 3278.9 (2) Å3 |
Triclinic, P1 | Z = 6 |
a = 15.3906 (6) Å | Cu Kα radiation |
b = 15.7040 (7) Å | µ = 2.83 mm−1 |
c = 15.9129 (7) Å | T = 100 K |
α = 89.568 (3)° | 0.35 × 0.15 × 0.03 mm |
β = 74.825 (4)° |
Agilent SuperNova Dual diffractometer with Atlas detector | 25266 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 18393 reflections with I > 2σ(I) |
Tmin = 0.437, Tmax = 0.920 | Rint = 0.075 |
38203 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.190 | H-atom parameters constrained |
S = 1.02 | Δρmax = 1.44 e Å−3 |
25266 reflections | Δρmin = −0.53 e Å−3 |
866 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 | ||
Cl1 | 0.28241 (5) | 0.07400 (5) | 0.46993 (5) | 0.04104 (17) | |
Cl2 | 0.54081 (6) | 0.09270 (5) | 0.45600 (5) | 0.04320 (17) | |
Cl3 | 0.88514 (6) | 0.05812 (5) | 0.48589 (5) | 0.04180 (17) | |
S1 | −0.09695 (4) | 0.50003 (4) | 0.38610 (4) | 0.02693 (13) | |
S2 | 0.26108 (5) | 0.55904 (5) | 0.35580 (4) | 0.03043 (14) | |
S3 | 0.59118 (4) | 0.50668 (4) | 0.36852 (4) | 0.02694 (13) | |
F1 | 0.17005 (17) | 0.91092 (16) | 0.12971 (16) | 0.0647 (6) | |
F2 | 0.2082 (2) | 0.9126 (2) | 0.24916 (15) | 0.0777 (8) | |
F3 | 0.30080 (15) | 0.79316 (15) | 0.14940 (14) | 0.0566 (5) | |
F4 | 0.48491 (15) | 0.96664 (14) | 0.10659 (13) | 0.0503 (5) | |
F5 | 0.55114 (16) | 0.98424 (14) | 0.20327 (12) | 0.0502 (5) | |
F6 | 0.63952 (13) | 0.86860 (13) | 0.09720 (12) | 0.0467 (4) | |
F7 | 0.7953 (2) | 0.9366 (2) | 0.10386 (19) | 0.0935 (10) | |
F8 | 0.8286 (3) | 0.9722 (2) | 0.21371 (15) | 0.1110 (13) | |
F9 | 0.93890 (18) | 0.85381 (17) | 0.12129 (18) | 0.0814 (8) | |
N1 | 0.03473 (16) | 0.38490 (15) | 0.23888 (13) | 0.0263 (4) | |
N2 | 0.02592 (15) | 0.53909 (14) | 0.26904 (13) | 0.0237 (4) | |
N3 | 0.27750 (16) | 0.40345 (16) | −0.01072 (14) | 0.0296 (5) | |
N4 | 0.12993 (15) | 0.58965 (15) | 0.17176 (13) | 0.0258 (4) | |
H4n | 0.1760 | 0.5755 | 0.1205 | 0.031* | |
N5 | 0.38696 (16) | 0.44653 (16) | 0.20522 (13) | 0.0274 (4) | |
N6 | 0.40376 (16) | 0.58285 (15) | 0.25038 (13) | 0.0273 (4) | |
N7 | 0.67800 (18) | 0.43372 (16) | −0.01233 (15) | 0.0344 (5) | |
N8 | 0.53033 (16) | 0.61660 (15) | 0.16659 (13) | 0.0272 (4) | |
H8n | 0.5864 | 0.5944 | 0.1224 | 0.033* | |
N9 | 0.73047 (16) | 0.39133 (15) | 0.22323 (13) | 0.0261 (4) | |
N10 | 0.72270 (15) | 0.54339 (14) | 0.26119 (13) | 0.0229 (4) | |
N11 | 0.98810 (17) | 0.41309 (16) | −0.00944 (14) | 0.0316 (5) | |
N12 | 0.83306 (15) | 0.59339 (14) | 0.17164 (13) | 0.0242 (4) | |
H12n | 0.8852 | 0.5766 | 0.1243 | 0.029* | |
C1 | −0.00049 (17) | 0.46909 (17) | 0.28614 (15) | 0.0242 (5) | |
C2 | 0.10854 (18) | 0.36623 (18) | 0.16294 (16) | 0.0256 (5) | |
C3 | 0.14142 (18) | 0.43437 (18) | 0.13701 (15) | 0.0249 (5) | |
C4 | 0.09820 (18) | 0.52258 (17) | 0.19325 (15) | 0.0236 (5) | |
C5 | −0.09619 (19) | 0.38575 (18) | 0.40321 (16) | 0.0272 (5) | |
H5A | −0.1556 | 0.3967 | 0.4534 | 0.033* | |
H5B | −0.1047 | 0.3610 | 0.3505 | 0.033* | |
C6 | −0.00106 (19) | 0.30952 (18) | 0.42101 (15) | 0.0266 (5) | |
C7 | 0.0331 (2) | 0.21336 (19) | 0.39186 (17) | 0.0321 (5) | |
H7 | −0.0040 | 0.1972 | 0.3614 | 0.038* | |
C8 | 0.1204 (2) | 0.14040 (19) | 0.40635 (17) | 0.0328 (6) | |
H8A | 0.1431 | 0.0749 | 0.3862 | 0.039* | |
C9 | 0.1735 (2) | 0.16499 (19) | 0.45067 (17) | 0.0310 (5) | |
C10 | 0.1415 (2) | 0.2598 (2) | 0.48143 (17) | 0.0325 (6) | |
H10 | 0.1785 | 0.2755 | 0.5124 | 0.039* | |
C11 | 0.0541 (2) | 0.33159 (18) | 0.46595 (17) | 0.0292 (5) | |
H11 | 0.0315 | 0.3970 | 0.4864 | 0.035* | |
C12 | 0.1518 (2) | 0.27018 (18) | 0.10984 (16) | 0.0292 (5) | |
H12A | 0.2077 | 0.2639 | 0.0581 | 0.035* | |
H12B | 0.0981 | 0.2680 | 0.0881 | 0.035* | |
C13 | 0.2646 (3) | 0.1856 (3) | 0.2067 (3) | 0.0562 (9) | |
H13A | 0.2868 | 0.1291 | 0.2381 | 0.084* | |
H13B | 0.2302 | 0.2444 | 0.2488 | 0.084* | |
H13C | 0.3241 | 0.1845 | 0.1639 | 0.084* | |
C14 | 0.1932 (2) | 0.1840 (2) | 0.1604 (2) | 0.0395 (6) | |
H14 | 0.1329 | 0.1882 | 0.2070 | 0.047* | |
C15 | 0.2373 (2) | 0.0905 (2) | 0.1034 (2) | 0.0397 (6) | |
H15A | 0.2627 | 0.0371 | 0.1377 | 0.060* | |
H15B | 0.2936 | 0.0852 | 0.0537 | 0.060* | |
H15C | 0.1845 | 0.0880 | 0.0815 | 0.060* | |
C16 | 0.21728 (19) | 0.41608 (17) | 0.05535 (16) | 0.0261 (5) | |
C17 | 0.10026 (19) | 0.67876 (18) | 0.21925 (16) | 0.0266 (5) | |
C18 | 0.0161 (2) | 0.7249 (2) | 0.29302 (18) | 0.0363 (6) | |
H18 | −0.0274 | 0.6970 | 0.3149 | 0.044* | |
C19 | −0.0034 (3) | 0.8118 (2) | 0.3341 (2) | 0.0450 (8) | |
H19 | −0.0602 | 0.8424 | 0.3848 | 0.054* | |
C20 | 0.0572 (2) | 0.8555 (2) | 0.30360 (19) | 0.0421 (7) | |
H20 | 0.0426 | 0.9151 | 0.3327 | 0.051* | |
C21 | 0.1402 (2) | 0.8094 (2) | 0.22893 (17) | 0.0327 (6) | |
C22 | 0.16137 (19) | 0.72244 (19) | 0.18721 (16) | 0.0281 (5) | |
H22 | 0.2180 | 0.6921 | 0.1363 | 0.034* | |
C23 | 0.2036 (2) | 0.8567 (2) | 0.1902 (2) | 0.0416 (7) | |
C24 | 0.36230 (18) | 0.52357 (18) | 0.25885 (16) | 0.0270 (5) | |
C25 | 0.46783 (18) | 0.42328 (18) | 0.13324 (16) | 0.0265 (5) | |
C26 | 0.52042 (18) | 0.47668 (18) | 0.12004 (16) | 0.0251 (5) | |
C27 | 0.48436 (18) | 0.56034 (18) | 0.17990 (16) | 0.0261 (5) | |
C28 | 0.23542 (19) | 0.4576 (2) | 0.36258 (17) | 0.0317 (6) | |
H28A | 0.1690 | 0.4771 | 0.4071 | 0.038* | |
H28B | 0.2290 | 0.4413 | 0.3053 | 0.038* | |
C29 | 0.31508 (19) | 0.36827 (19) | 0.38604 (16) | 0.0282 (5) | |
C30 | 0.3587 (2) | 0.2816 (2) | 0.33236 (19) | 0.0410 (7) | |
H30 | 0.3405 | 0.2805 | 0.2799 | 0.049* | |
C31 | 0.4279 (3) | 0.1970 (2) | 0.35333 (19) | 0.0432 (7) | |
H31 | 0.4561 | 0.1379 | 0.3164 | 0.052* | |
C32 | 0.4553 (2) | 0.19952 (19) | 0.42846 (17) | 0.0322 (6) | |
C33 | 0.41735 (19) | 0.28512 (19) | 0.48200 (17) | 0.0289 (5) | |
H33 | 0.4393 | 0.2864 | 0.5323 | 0.035* | |
C34 | 0.34619 (18) | 0.36938 (18) | 0.46041 (16) | 0.0267 (5) | |
H34 | 0.3185 | 0.4285 | 0.4971 | 0.032* | |
C35 | 0.4953 (2) | 0.33835 (19) | 0.07026 (17) | 0.0298 (5) | |
H35A | 0.5464 | 0.3356 | 0.0161 | 0.036* | |
H35B | 0.4337 | 0.3482 | 0.0541 | 0.036* | |
C36 | 0.5468 (3) | 0.1638 (2) | 0.0437 (2) | 0.0517 (9) | |
H36A | 0.5728 | 0.1024 | 0.0679 | 0.078* | |
H36B | 0.5939 | 0.1578 | −0.0136 | 0.078* | |
H36C | 0.4797 | 0.1804 | 0.0369 | 0.078* | |
C37 | 0.5375 (2) | 0.2426 (2) | 0.10586 (19) | 0.0399 (7) | |
H37 | 0.4883 | 0.2483 | 0.1635 | 0.048* | |
C38 | 0.6384 (3) | 0.2182 (3) | 0.1213 (3) | 0.0643 (11) | |
H38A | 0.6297 | 0.2696 | 0.1623 | 0.096* | |
H38B | 0.6880 | 0.2120 | 0.0654 | 0.096* | |
H38C | 0.6630 | 0.1572 | 0.1461 | 0.096* | |
C39 | 0.60785 (19) | 0.45106 (18) | 0.04593 (17) | 0.0280 (5) | |
C40 | 0.50169 (19) | 0.70637 (18) | 0.21335 (16) | 0.0271 (5) | |
C41 | 0.4449 (2) | 0.73593 (19) | 0.30145 (17) | 0.0312 (5) | |
H41 | 0.4219 | 0.6954 | 0.3341 | 0.037* | |
C42 | 0.4221 (2) | 0.8246 (2) | 0.34108 (18) | 0.0377 (6) | |
H42 | 0.3828 | 0.8448 | 0.4009 | 0.045* | |
C43 | 0.4557 (2) | 0.8845 (2) | 0.29504 (18) | 0.0359 (6) | |
H43 | 0.4398 | 0.9453 | 0.3227 | 0.043* | |
C44 | 0.51292 (19) | 0.85383 (18) | 0.20761 (17) | 0.0293 (5) | |
C45 | 0.53599 (19) | 0.76585 (18) | 0.16691 (16) | 0.0280 (5) | |
H45 | 0.5754 | 0.7459 | 0.1071 | 0.034* | |
C46 | 0.5468 (2) | 0.9177 (2) | 0.15434 (18) | 0.0341 (6) | |
C47 | 0.69373 (18) | 0.47470 (17) | 0.27320 (16) | 0.0244 (5) | |
C48 | 0.80934 (19) | 0.37318 (18) | 0.15126 (16) | 0.0253 (5) | |
C49 | 0.84461 (18) | 0.44015 (17) | 0.13139 (15) | 0.0244 (5) | |
C50 | 0.79899 (17) | 0.52733 (17) | 0.18920 (15) | 0.0225 (5) | |
C51 | 0.57135 (19) | 0.40147 (19) | 0.37399 (18) | 0.0301 (5) | |
H51A | 0.5033 | 0.4196 | 0.4152 | 0.036* | |
H51B | 0.5708 | 0.3818 | 0.3153 | 0.036* | |
C52 | 0.64989 (18) | 0.31549 (18) | 0.40284 (16) | 0.0272 (5) | |
C53 | 0.6869 (2) | 0.2237 (2) | 0.36093 (18) | 0.0326 (6) | |
H53 | 0.6631 | 0.2152 | 0.3138 | 0.039* | |
C54 | 0.7585 (2) | 0.14369 (19) | 0.38691 (18) | 0.0343 (6) | |
H54 | 0.7831 | 0.0808 | 0.3584 | 0.041* | |
C55 | 0.7929 (2) | 0.15728 (19) | 0.45457 (17) | 0.0302 (5) | |
C56 | 0.7568 (2) | 0.2475 (2) | 0.49877 (17) | 0.0322 (5) | |
H56 | 0.7804 | 0.2554 | 0.5461 | 0.039* | |
C57 | 0.68469 (19) | 0.32682 (19) | 0.47215 (17) | 0.0295 (5) | |
H57 | 0.6590 | 0.3895 | 0.5018 | 0.035* | |
C58 | 0.8553 (2) | 0.27941 (18) | 0.09367 (17) | 0.0322 (6) | |
H58A | 0.9213 | 0.2686 | 0.0529 | 0.039* | |
H58B | 0.8098 | 0.2845 | 0.0578 | 0.039* | |
C59 | 0.9241 (3) | 0.1005 (2) | 0.0764 (2) | 0.0438 (7) | |
H59A | 0.8819 | 0.1086 | 0.0374 | 0.066* | |
H59B | 0.9312 | 0.0446 | 0.1074 | 0.066* | |
H59C | 0.9916 | 0.0904 | 0.0417 | 0.066* | |
C60 | 0.8735 (2) | 0.19117 (19) | 0.14328 (17) | 0.0307 (5) | |
H60 | 0.8057 | 0.1991 | 0.1790 | 0.037* | |
C61 | 0.9363 (2) | 0.1818 (2) | 0.2048 (2) | 0.0437 (7) | |
H61A | 0.9021 | 0.2405 | 0.2469 | 0.066* | |
H61B | 1.0037 | 0.1726 | 0.1709 | 0.066* | |
H61C | 0.9438 | 0.1263 | 0.2364 | 0.066* | |
C62 | 0.92467 (19) | 0.42335 (17) | 0.05287 (16) | 0.0257 (5) | |
C63 | 0.79769 (18) | 0.68498 (17) | 0.21762 (16) | 0.0242 (5) | |
C64 | 0.7342 (2) | 0.71623 (19) | 0.30330 (16) | 0.0303 (5) | |
H64 | 0.7108 | 0.6754 | 0.3347 | 0.036* | |
C65 | 0.7051 (2) | 0.8073 (2) | 0.34271 (18) | 0.0344 (6) | |
H65 | 0.6613 | 0.8282 | 0.4012 | 0.041* | |
C66 | 0.7384 (2) | 0.86838 (19) | 0.29861 (17) | 0.0315 (5) | |
H66 | 0.7174 | 0.9309 | 0.3260 | 0.038* | |
C67 | 0.8028 (2) | 0.83617 (19) | 0.21389 (17) | 0.0297 (5) | |
C68 | 0.83219 (19) | 0.74554 (18) | 0.17302 (16) | 0.0283 (5) | |
H68 | 0.8759 | 0.7248 | 0.1145 | 0.034* | |
C69 | 0.8404 (2) | 0.8999 (2) | 0.16351 (18) | 0.0380 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0405 (4) | 0.0330 (3) | 0.0356 (3) | −0.0047 (3) | −0.0127 (3) | 0.0000 (3) |
Cl2 | 0.0407 (4) | 0.0286 (3) | 0.0438 (4) | −0.0078 (3) | −0.0023 (3) | 0.0072 (3) |
Cl3 | 0.0428 (4) | 0.0302 (3) | 0.0434 (4) | −0.0096 (3) | −0.0128 (3) | 0.0082 (3) |
S1 | 0.0247 (3) | 0.0270 (3) | 0.0246 (3) | −0.0116 (2) | −0.0014 (2) | 0.0035 (2) |
S2 | 0.0274 (3) | 0.0317 (3) | 0.0238 (3) | −0.0099 (2) | −0.0017 (2) | 0.0056 (2) |
S3 | 0.0243 (3) | 0.0263 (3) | 0.0262 (3) | −0.0116 (2) | −0.0016 (2) | 0.0036 (2) |
F1 | 0.0703 (14) | 0.0676 (14) | 0.0796 (15) | −0.0485 (12) | −0.0286 (12) | 0.0407 (12) |
F2 | 0.1067 (19) | 0.1026 (19) | 0.0552 (13) | −0.0886 (17) | 0.0028 (12) | −0.0138 (12) |
F3 | 0.0438 (10) | 0.0621 (13) | 0.0698 (13) | −0.0359 (10) | −0.0047 (9) | 0.0128 (10) |
F4 | 0.0558 (11) | 0.0463 (10) | 0.0636 (12) | −0.0297 (9) | −0.0300 (10) | 0.0288 (9) |
F5 | 0.0718 (13) | 0.0456 (10) | 0.0407 (10) | −0.0399 (10) | −0.0046 (9) | −0.0026 (8) |
F6 | 0.0421 (10) | 0.0383 (9) | 0.0470 (10) | −0.0198 (8) | 0.0086 (8) | 0.0023 (8) |
F7 | 0.121 (2) | 0.124 (2) | 0.108 (2) | −0.098 (2) | −0.0713 (19) | 0.0905 (19) |
F8 | 0.214 (4) | 0.096 (2) | 0.0456 (13) | −0.126 (2) | 0.0278 (17) | −0.0165 (12) |
F9 | 0.0590 (14) | 0.0630 (14) | 0.104 (2) | −0.0338 (12) | 0.0138 (13) | 0.0301 (13) |
N1 | 0.0272 (10) | 0.0292 (10) | 0.0217 (10) | −0.0142 (9) | −0.0037 (8) | 0.0032 (8) |
N2 | 0.0210 (9) | 0.0258 (10) | 0.0222 (10) | −0.0103 (8) | −0.0044 (8) | 0.0039 (8) |
N3 | 0.0290 (11) | 0.0293 (11) | 0.0254 (11) | −0.0117 (9) | −0.0036 (9) | 0.0027 (8) |
N4 | 0.0245 (10) | 0.0273 (10) | 0.0223 (10) | −0.0123 (8) | −0.0012 (8) | 0.0018 (8) |
N5 | 0.0257 (10) | 0.0318 (11) | 0.0238 (10) | −0.0127 (9) | −0.0074 (8) | 0.0057 (8) |
N6 | 0.0259 (10) | 0.0278 (10) | 0.0228 (10) | −0.0096 (8) | −0.0043 (8) | 0.0036 (8) |
N7 | 0.0350 (12) | 0.0298 (11) | 0.0294 (12) | −0.0128 (10) | 0.0001 (10) | 0.0012 (9) |
N8 | 0.0257 (10) | 0.0262 (10) | 0.0233 (10) | −0.0099 (8) | −0.0012 (8) | 0.0013 (8) |
N9 | 0.0269 (10) | 0.0259 (10) | 0.0250 (10) | −0.0124 (8) | −0.0065 (8) | 0.0034 (8) |
N10 | 0.0219 (9) | 0.0247 (10) | 0.0217 (10) | −0.0108 (8) | −0.0056 (8) | 0.0034 (8) |
N11 | 0.0341 (12) | 0.0277 (11) | 0.0278 (11) | −0.0140 (9) | −0.0016 (9) | 0.0009 (8) |
N12 | 0.0252 (10) | 0.0232 (10) | 0.0209 (9) | −0.0115 (8) | −0.0013 (8) | 0.0003 (7) |
C1 | 0.0217 (11) | 0.0268 (12) | 0.0222 (11) | −0.0093 (9) | −0.0071 (9) | 0.0064 (9) |
C2 | 0.0266 (12) | 0.0269 (12) | 0.0238 (12) | −0.0118 (10) | −0.0095 (10) | 0.0056 (9) |
C3 | 0.0238 (11) | 0.0277 (12) | 0.0210 (11) | −0.0102 (10) | −0.0064 (9) | 0.0041 (9) |
C4 | 0.0213 (11) | 0.0269 (12) | 0.0228 (11) | −0.0111 (9) | −0.0070 (9) | 0.0061 (9) |
C5 | 0.0271 (12) | 0.0275 (12) | 0.0271 (12) | −0.0161 (10) | −0.0016 (10) | 0.0046 (9) |
C6 | 0.0295 (12) | 0.0287 (12) | 0.0203 (11) | −0.0150 (10) | −0.0027 (9) | 0.0060 (9) |
C7 | 0.0408 (14) | 0.0320 (13) | 0.0271 (13) | −0.0196 (12) | −0.0108 (11) | 0.0057 (10) |
C8 | 0.0449 (15) | 0.0256 (12) | 0.0259 (13) | −0.0158 (12) | −0.0085 (11) | 0.0039 (10) |
C9 | 0.0337 (13) | 0.0284 (13) | 0.0230 (12) | −0.0103 (11) | −0.0040 (10) | 0.0047 (10) |
C10 | 0.0328 (13) | 0.0348 (14) | 0.0291 (13) | −0.0157 (11) | −0.0079 (11) | 0.0019 (10) |
C11 | 0.0316 (13) | 0.0262 (12) | 0.0280 (13) | −0.0141 (10) | −0.0047 (10) | 0.0004 (10) |
C12 | 0.0330 (13) | 0.0295 (13) | 0.0247 (12) | −0.0164 (11) | −0.0043 (10) | 0.0014 (10) |
C13 | 0.052 (2) | 0.053 (2) | 0.061 (2) | −0.0204 (17) | −0.0201 (17) | 0.0047 (17) |
C14 | 0.0391 (15) | 0.0330 (14) | 0.0354 (15) | −0.0076 (12) | −0.0114 (12) | 0.0006 (12) |
C15 | 0.0395 (15) | 0.0310 (14) | 0.0473 (17) | −0.0174 (12) | −0.0091 (13) | 0.0054 (12) |
C16 | 0.0276 (12) | 0.0242 (11) | 0.0254 (12) | −0.0111 (10) | −0.0080 (10) | 0.0033 (9) |
C17 | 0.0278 (12) | 0.0278 (12) | 0.0242 (12) | −0.0134 (10) | −0.0067 (10) | 0.0045 (9) |
C18 | 0.0393 (15) | 0.0348 (14) | 0.0317 (14) | −0.0214 (12) | 0.0021 (12) | 0.0010 (11) |
C19 | 0.0502 (18) | 0.0415 (16) | 0.0342 (15) | −0.0260 (15) | 0.0109 (13) | −0.0085 (12) |
C20 | 0.0521 (18) | 0.0383 (16) | 0.0337 (15) | −0.0265 (14) | 0.0017 (13) | −0.0074 (12) |
C21 | 0.0390 (14) | 0.0353 (14) | 0.0299 (13) | −0.0237 (12) | −0.0078 (11) | 0.0037 (11) |
C22 | 0.0289 (12) | 0.0332 (13) | 0.0228 (12) | −0.0170 (11) | −0.0041 (10) | 0.0042 (10) |
C23 | 0.0485 (17) | 0.0475 (17) | 0.0375 (15) | −0.0325 (15) | −0.0073 (13) | 0.0030 (13) |
C24 | 0.0219 (11) | 0.0311 (12) | 0.0242 (12) | −0.0096 (10) | −0.0061 (9) | 0.0071 (10) |
C25 | 0.0252 (12) | 0.0295 (12) | 0.0222 (11) | −0.0101 (10) | −0.0080 (9) | 0.0055 (9) |
C26 | 0.0231 (11) | 0.0285 (12) | 0.0222 (11) | −0.0110 (10) | −0.0062 (9) | 0.0042 (9) |
C27 | 0.0244 (11) | 0.0274 (12) | 0.0223 (11) | −0.0085 (10) | −0.0071 (9) | 0.0044 (9) |
C28 | 0.0256 (12) | 0.0444 (15) | 0.0261 (13) | −0.0177 (11) | −0.0066 (10) | 0.0093 (11) |
C29 | 0.0244 (12) | 0.0364 (14) | 0.0242 (12) | −0.0166 (11) | −0.0035 (9) | 0.0065 (10) |
C30 | 0.0520 (18) | 0.0446 (17) | 0.0280 (14) | −0.0248 (15) | −0.0095 (13) | 0.0003 (12) |
C31 | 0.0567 (19) | 0.0321 (15) | 0.0314 (15) | −0.0171 (14) | −0.0049 (13) | −0.0048 (11) |
C32 | 0.0303 (13) | 0.0297 (13) | 0.0289 (13) | −0.0122 (11) | 0.0001 (10) | 0.0055 (10) |
C33 | 0.0270 (12) | 0.0315 (13) | 0.0255 (12) | −0.0144 (10) | −0.0022 (10) | 0.0038 (10) |
C34 | 0.0229 (11) | 0.0279 (12) | 0.0263 (12) | −0.0120 (10) | −0.0019 (9) | 0.0018 (9) |
C35 | 0.0291 (12) | 0.0367 (14) | 0.0249 (12) | −0.0168 (11) | −0.0073 (10) | 0.0035 (10) |
C36 | 0.083 (3) | 0.0443 (18) | 0.0380 (17) | −0.0402 (18) | −0.0142 (16) | 0.0065 (14) |
C37 | 0.0517 (18) | 0.0362 (15) | 0.0330 (15) | −0.0217 (14) | −0.0122 (13) | 0.0052 (12) |
C38 | 0.066 (2) | 0.0346 (17) | 0.095 (3) | −0.0128 (17) | −0.048 (2) | 0.0052 (18) |
C39 | 0.0310 (13) | 0.0238 (12) | 0.0280 (13) | −0.0113 (10) | −0.0094 (11) | 0.0034 (9) |
C40 | 0.0258 (12) | 0.0279 (12) | 0.0232 (12) | −0.0092 (10) | −0.0065 (9) | 0.0027 (9) |
C41 | 0.0360 (14) | 0.0310 (13) | 0.0233 (12) | −0.0155 (11) | −0.0040 (10) | 0.0048 (10) |
C42 | 0.0429 (16) | 0.0387 (15) | 0.0245 (13) | −0.0185 (13) | 0.0002 (11) | −0.0021 (11) |
C43 | 0.0379 (15) | 0.0293 (13) | 0.0330 (14) | −0.0144 (12) | −0.0011 (11) | −0.0056 (11) |
C44 | 0.0284 (12) | 0.0270 (12) | 0.0288 (13) | −0.0113 (10) | −0.0056 (10) | 0.0026 (10) |
C45 | 0.0246 (12) | 0.0303 (13) | 0.0238 (12) | −0.0106 (10) | −0.0029 (9) | 0.0026 (9) |
C46 | 0.0349 (14) | 0.0308 (13) | 0.0330 (14) | −0.0154 (11) | −0.0040 (11) | 0.0002 (11) |
C47 | 0.0231 (11) | 0.0254 (11) | 0.0244 (11) | −0.0103 (9) | −0.0085 (9) | 0.0065 (9) |
C48 | 0.0282 (12) | 0.0257 (12) | 0.0232 (11) | −0.0133 (10) | −0.0080 (10) | 0.0054 (9) |
C49 | 0.0254 (11) | 0.0238 (11) | 0.0218 (11) | −0.0101 (9) | −0.0060 (9) | 0.0036 (9) |
C50 | 0.0209 (11) | 0.0240 (11) | 0.0216 (11) | −0.0094 (9) | −0.0068 (9) | 0.0043 (9) |
C51 | 0.0231 (12) | 0.0338 (13) | 0.0336 (14) | −0.0149 (11) | −0.0056 (10) | 0.0082 (11) |
C52 | 0.0243 (12) | 0.0290 (12) | 0.0255 (12) | −0.0130 (10) | −0.0022 (9) | 0.0067 (10) |
C53 | 0.0355 (14) | 0.0348 (14) | 0.0282 (13) | −0.0186 (12) | −0.0063 (11) | 0.0043 (11) |
C54 | 0.0402 (15) | 0.0268 (13) | 0.0312 (14) | −0.0148 (11) | −0.0048 (11) | 0.0014 (10) |
C55 | 0.0274 (12) | 0.0290 (13) | 0.0287 (13) | −0.0119 (10) | −0.0021 (10) | 0.0059 (10) |
C56 | 0.0334 (13) | 0.0344 (14) | 0.0262 (13) | −0.0150 (11) | −0.0065 (10) | 0.0040 (10) |
C57 | 0.0295 (12) | 0.0278 (12) | 0.0276 (12) | −0.0135 (10) | −0.0022 (10) | 0.0005 (10) |
C58 | 0.0403 (14) | 0.0265 (13) | 0.0284 (13) | −0.0176 (11) | −0.0042 (11) | 0.0007 (10) |
C59 | 0.0546 (19) | 0.0294 (14) | 0.0396 (16) | −0.0208 (14) | 0.0009 (14) | 0.0007 (12) |
C60 | 0.0303 (13) | 0.0271 (13) | 0.0332 (13) | −0.0142 (11) | −0.0055 (11) | 0.0033 (10) |
C61 | 0.0409 (16) | 0.0335 (15) | 0.059 (2) | −0.0153 (13) | −0.0221 (15) | 0.0100 (13) |
C62 | 0.0300 (12) | 0.0197 (11) | 0.0262 (12) | −0.0107 (9) | −0.0080 (10) | 0.0022 (9) |
C63 | 0.0244 (11) | 0.0235 (11) | 0.0235 (11) | −0.0110 (9) | −0.0058 (9) | 0.0025 (9) |
C64 | 0.0373 (14) | 0.0287 (13) | 0.0238 (12) | −0.0182 (11) | −0.0021 (10) | 0.0023 (10) |
C65 | 0.0387 (14) | 0.0347 (14) | 0.0255 (13) | −0.0199 (12) | 0.0023 (11) | −0.0010 (10) |
C66 | 0.0355 (14) | 0.0277 (13) | 0.0286 (13) | −0.0165 (11) | −0.0022 (11) | −0.0003 (10) |
C67 | 0.0324 (13) | 0.0281 (12) | 0.0272 (13) | −0.0159 (11) | −0.0034 (10) | 0.0047 (10) |
C68 | 0.0302 (12) | 0.0301 (13) | 0.0211 (11) | −0.0144 (10) | −0.0011 (10) | 0.0017 (9) |
C69 | 0.0503 (17) | 0.0345 (14) | 0.0268 (13) | −0.0243 (13) | 0.0008 (12) | 0.0018 (11) |
Cl1—C9 | 1.741 (3) | C22—H22 | 0.9500 |
Cl2—C32 | 1.738 (3) | C25—C26 | 1.388 (3) |
Cl3—C55 | 1.743 (3) | C25—C35 | 1.499 (4) |
S1—C1 | 1.758 (2) | C26—C27 | 1.422 (3) |
S1—C5 | 1.808 (2) | C26—C39 | 1.431 (3) |
S2—C24 | 1.756 (2) | C28—C29 | 1.510 (4) |
S2—C28 | 1.803 (3) | C28—H28A | 0.9900 |
S3—C47 | 1.756 (2) | C28—H28B | 0.9900 |
S3—C51 | 1.809 (3) | C29—C30 | 1.385 (4) |
F1—C23 | 1.328 (4) | C29—C34 | 1.391 (4) |
F2—C23 | 1.327 (4) | C30—C31 | 1.381 (4) |
F3—C23 | 1.342 (4) | C30—H30 | 0.9500 |
F4—C46 | 1.334 (3) | C31—C32 | 1.375 (4) |
F5—C46 | 1.343 (3) | C31—H31 | 0.9500 |
F6—C46 | 1.338 (3) | C32—C33 | 1.385 (4) |
F7—C69 | 1.300 (4) | C33—C34 | 1.393 (4) |
F8—C69 | 1.309 (4) | C33—H33 | 0.9500 |
F9—C69 | 1.323 (4) | C34—H34 | 0.9500 |
N1—C1 | 1.326 (3) | C35—C37 | 1.515 (4) |
N1—C2 | 1.349 (3) | C35—H35A | 0.9900 |
N2—C1 | 1.338 (3) | C35—H35B | 0.9900 |
N2—C4 | 1.341 (3) | C36—C37 | 1.521 (4) |
N3—C16 | 1.153 (3) | C36—H36A | 0.9800 |
N4—C4 | 1.356 (3) | C36—H36B | 0.9800 |
N4—C17 | 1.412 (3) | C36—H36C | 0.9800 |
N4—H4n | 0.8800 | C37—C38 | 1.508 (5) |
N5—C24 | 1.328 (3) | C37—H37 | 1.0000 |
N5—C25 | 1.357 (3) | C38—H38A | 0.9800 |
N6—C24 | 1.336 (3) | C38—H38B | 0.9800 |
N6—C27 | 1.342 (3) | C38—H38C | 0.9800 |
N7—C39 | 1.145 (3) | C40—C45 | 1.390 (3) |
N8—C27 | 1.346 (3) | C40—C41 | 1.395 (3) |
N8—C40 | 1.419 (3) | C41—C42 | 1.383 (4) |
N8—H8n | 0.8800 | C41—H41 | 0.9500 |
N9—C47 | 1.332 (3) | C42—C43 | 1.387 (4) |
N9—C48 | 1.352 (3) | C42—H42 | 0.9500 |
N10—C50 | 1.336 (3) | C43—C44 | 1.388 (4) |
N10—C47 | 1.337 (3) | C43—H43 | 0.9500 |
N11—C62 | 1.147 (3) | C44—C45 | 1.379 (4) |
N12—C50 | 1.357 (3) | C44—C46 | 1.493 (4) |
N12—C63 | 1.413 (3) | C45—H45 | 0.9500 |
N12—H12n | 0.8800 | C48—C49 | 1.387 (3) |
C2—C3 | 1.396 (3) | C48—C58 | 1.498 (3) |
C2—C12 | 1.498 (3) | C49—C50 | 1.422 (3) |
C3—C4 | 1.426 (3) | C49—C62 | 1.433 (3) |
C3—C16 | 1.429 (3) | C51—C52 | 1.514 (3) |
C5—C6 | 1.509 (3) | C51—H51A | 0.9900 |
C5—H5A | 0.9900 | C51—H51B | 0.9900 |
C5—H5B | 0.9900 | C52—C53 | 1.385 (4) |
C6—C7 | 1.391 (4) | C52—C57 | 1.391 (4) |
C6—C11 | 1.393 (4) | C53—C54 | 1.391 (4) |
C7—C8 | 1.389 (4) | C53—H53 | 0.9500 |
C7—H7 | 0.9500 | C54—C55 | 1.375 (4) |
C8—C9 | 1.381 (4) | C54—H54 | 0.9500 |
C8—H8A | 0.9500 | C55—C56 | 1.381 (4) |
C9—C10 | 1.385 (4) | C56—C57 | 1.394 (4) |
C10—C11 | 1.391 (4) | C56—H56 | 0.9500 |
C10—H10 | 0.9500 | C57—H57 | 0.9500 |
C11—H11 | 0.9500 | C58—C60 | 1.539 (4) |
C12—C14 | 1.534 (4) | C58—H58A | 0.9900 |
C12—H12A | 0.9900 | C58—H58B | 0.9900 |
C12—H12B | 0.9900 | C59—C60 | 1.531 (4) |
C13—C14 | 1.485 (5) | C59—H59A | 0.9800 |
C13—H13A | 0.9800 | C59—H59B | 0.9800 |
C13—H13B | 0.9800 | C59—H59C | 0.9800 |
C13—H13C | 0.9800 | C60—C61 | 1.509 (4) |
C14—C15 | 1.492 (4) | C60—H60 | 1.0000 |
C14—H14 | 1.0000 | C61—H61A | 0.9800 |
C15—H15A | 0.9800 | C61—H61B | 0.9800 |
C15—H15B | 0.9800 | C61—H61C | 0.9800 |
C15—H15C | 0.9800 | C63—C64 | 1.390 (3) |
C17—C22 | 1.395 (3) | C63—C68 | 1.393 (3) |
C17—C18 | 1.395 (4) | C64—C65 | 1.386 (4) |
C18—C19 | 1.385 (4) | C64—H64 | 0.9500 |
C18—H18 | 0.9500 | C65—C66 | 1.388 (4) |
C19—C20 | 1.383 (4) | C65—H65 | 0.9500 |
C19—H19 | 0.9500 | C66—C67 | 1.382 (4) |
C20—C21 | 1.395 (4) | C66—H66 | 0.9500 |
C20—H20 | 0.9500 | C67—C68 | 1.389 (4) |
C21—C22 | 1.381 (4) | C67—C69 | 1.500 (3) |
C21—C23 | 1.490 (4) | C68—H68 | 0.9500 |
C1—S1—C5 | 101.53 (11) | C29—C34—H34 | 119.5 |
C24—S2—C28 | 102.77 (13) | C33—C34—H34 | 119.5 |
C47—S3—C51 | 103.16 (12) | C25—C35—C37 | 114.1 (2) |
C1—N1—C2 | 115.7 (2) | C25—C35—H35A | 108.7 |
C1—N2—C4 | 116.0 (2) | C37—C35—H35A | 108.7 |
C4—N4—C17 | 129.8 (2) | C25—C35—H35B | 108.7 |
C4—N4—H4n | 115.1 | C37—C35—H35B | 108.7 |
C17—N4—H4n | 115.1 | H35A—C35—H35B | 107.6 |
C24—N5—C25 | 115.1 (2) | C37—C36—H36A | 109.5 |
C24—N6—C27 | 116.4 (2) | C37—C36—H36B | 109.5 |
C27—N8—C40 | 129.6 (2) | H36A—C36—H36B | 109.5 |
C27—N8—H8n | 115.2 | C37—C36—H36C | 109.5 |
C40—N8—H8n | 115.2 | H36A—C36—H36C | 109.5 |
C47—N9—C48 | 115.2 (2) | H36B—C36—H36C | 109.5 |
C50—N10—C47 | 116.3 (2) | C38—C37—C35 | 111.0 (3) |
C50—N12—C63 | 129.9 (2) | C38—C37—C36 | 111.4 (3) |
C50—N12—H12n | 115.0 | C35—C37—C36 | 110.0 (2) |
C63—N12—H12n | 115.0 | C38—C37—H37 | 108.1 |
N1—C1—N2 | 129.3 (2) | C35—C37—H37 | 108.1 |
N1—C1—S1 | 119.08 (18) | C36—C37—H37 | 108.1 |
N2—C1—S1 | 111.62 (18) | C37—C38—H38A | 109.5 |
N1—C2—C3 | 120.4 (2) | C37—C38—H38B | 109.5 |
N1—C2—C12 | 116.7 (2) | H38A—C38—H38B | 109.5 |
C3—C2—C12 | 122.9 (2) | C37—C38—H38C | 109.5 |
C2—C3—C4 | 119.0 (2) | H38A—C38—H38C | 109.5 |
C2—C3—C16 | 120.6 (2) | H38B—C38—H38C | 109.5 |
C4—C3—C16 | 120.4 (2) | N7—C39—C26 | 177.3 (3) |
N2—C4—N4 | 119.5 (2) | C45—C40—C41 | 119.5 (2) |
N2—C4—C3 | 119.6 (2) | C45—C40—N8 | 116.2 (2) |
N4—C4—C3 | 121.0 (2) | C41—C40—N8 | 124.3 (2) |
C6—C5—S1 | 114.73 (17) | C42—C41—C40 | 119.6 (2) |
C6—C5—H5A | 108.6 | C42—C41—H41 | 120.2 |
S1—C5—H5A | 108.6 | C40—C41—H41 | 120.2 |
C6—C5—H5B | 108.6 | C41—C42—C43 | 121.2 (3) |
S1—C5—H5B | 108.6 | C41—C42—H42 | 119.4 |
H5A—C5—H5B | 107.6 | C43—C42—H42 | 119.4 |
C7—C6—C11 | 118.4 (2) | C42—C43—C44 | 118.5 (3) |
C7—C6—C5 | 119.0 (2) | C42—C43—H43 | 120.7 |
C11—C6—C5 | 122.5 (2) | C44—C43—H43 | 120.7 |
C8—C7—C6 | 121.3 (3) | C45—C44—C43 | 121.0 (2) |
C8—C7—H7 | 119.3 | C45—C44—C46 | 118.5 (2) |
C6—C7—H7 | 119.3 | C43—C44—C46 | 120.4 (2) |
C9—C8—C7 | 118.7 (2) | C44—C45—C40 | 120.1 (2) |
C9—C8—H8A | 120.7 | C44—C45—H45 | 120.0 |
C7—C8—H8A | 120.7 | C40—C45—H45 | 120.0 |
C8—C9—C10 | 121.8 (3) | F4—C46—F6 | 105.8 (2) |
C8—C9—Cl1 | 119.0 (2) | F4—C46—F5 | 105.9 (2) |
C10—C9—Cl1 | 119.2 (2) | F6—C46—F5 | 106.2 (2) |
C9—C10—C11 | 118.5 (3) | F4—C46—C44 | 112.5 (2) |
C9—C10—H10 | 120.8 | F6—C46—C44 | 112.5 (2) |
C11—C10—H10 | 120.8 | F5—C46—C44 | 113.2 (2) |
C10—C11—C6 | 121.3 (2) | N9—C47—N10 | 129.1 (2) |
C10—C11—H11 | 119.3 | N9—C47—S3 | 119.56 (18) |
C6—C11—H11 | 119.3 | N10—C47—S3 | 111.38 (18) |
C2—C12—C14 | 114.1 (2) | N9—C48—C49 | 120.7 (2) |
C2—C12—H12A | 108.7 | N9—C48—C58 | 117.5 (2) |
C14—C12—H12A | 108.7 | C49—C48—C58 | 121.7 (2) |
C2—C12—H12B | 108.7 | C48—C49—C50 | 119.2 (2) |
C14—C12—H12B | 108.7 | C48—C49—C62 | 120.9 (2) |
H12A—C12—H12B | 107.6 | C50—C49—C62 | 119.9 (2) |
C14—C13—H13A | 109.5 | N10—C50—N12 | 120.3 (2) |
C14—C13—H13B | 109.5 | N10—C50—C49 | 119.4 (2) |
H13A—C13—H13B | 109.5 | N12—C50—C49 | 120.3 (2) |
C14—C13—H13C | 109.5 | C52—C51—S3 | 115.19 (18) |
H13A—C13—H13C | 109.5 | C52—C51—H51A | 108.5 |
H13B—C13—H13C | 109.5 | S3—C51—H51A | 108.5 |
C13—C14—C15 | 111.8 (3) | C52—C51—H51B | 108.5 |
C13—C14—C12 | 114.2 (3) | S3—C51—H51B | 108.5 |
C15—C14—C12 | 111.5 (2) | H51A—C51—H51B | 107.5 |
C13—C14—H14 | 106.2 | C53—C52—C57 | 119.0 (2) |
C15—C14—H14 | 106.2 | C53—C52—C51 | 120.0 (2) |
C12—C14—H14 | 106.2 | C57—C52—C51 | 121.0 (2) |
C14—C15—H15A | 109.5 | C52—C53—C54 | 120.8 (3) |
C14—C15—H15B | 109.5 | C52—C53—H53 | 119.6 |
H15A—C15—H15B | 109.5 | C54—C53—H53 | 119.6 |
C14—C15—H15C | 109.5 | C55—C54—C53 | 118.9 (3) |
H15A—C15—H15C | 109.5 | C55—C54—H54 | 120.6 |
H15B—C15—H15C | 109.5 | C53—C54—H54 | 120.6 |
N3—C16—C3 | 178.5 (3) | C54—C55—C56 | 122.0 (3) |
C22—C17—C18 | 119.2 (2) | C54—C55—Cl3 | 119.4 (2) |
C22—C17—N4 | 115.5 (2) | C56—C55—Cl3 | 118.6 (2) |
C18—C17—N4 | 125.3 (2) | C55—C56—C57 | 118.4 (3) |
C19—C18—C17 | 119.2 (3) | C55—C56—H56 | 120.8 |
C19—C18—H18 | 120.4 | C57—C56—H56 | 120.8 |
C17—C18—H18 | 120.4 | C52—C57—C56 | 120.9 (2) |
C20—C19—C18 | 122.2 (3) | C52—C57—H57 | 119.5 |
C20—C19—H19 | 118.9 | C56—C57—H57 | 119.5 |
C18—C19—H19 | 118.9 | C48—C58—C60 | 114.7 (2) |
C19—C20—C21 | 118.0 (3) | C48—C58—H58A | 108.6 |
C19—C20—H20 | 121.0 | C60—C58—H58A | 108.6 |
C21—C20—H20 | 121.0 | C48—C58—H58B | 108.6 |
C22—C21—C20 | 120.8 (2) | C60—C58—H58B | 108.6 |
C22—C21—C23 | 119.1 (3) | H58A—C58—H58B | 107.6 |
C20—C21—C23 | 120.0 (3) | C60—C59—H59A | 109.5 |
C21—C22—C17 | 120.5 (2) | C60—C59—H59B | 109.5 |
C21—C22—H22 | 119.7 | H59A—C59—H59B | 109.5 |
C17—C22—H22 | 119.7 | C60—C59—H59C | 109.5 |
F2—C23—F1 | 107.0 (3) | H59A—C59—H59C | 109.5 |
F2—C23—F3 | 105.3 (3) | H59B—C59—H59C | 109.5 |
F1—C23—F3 | 105.3 (3) | C61—C60—C59 | 111.2 (2) |
F2—C23—C21 | 113.4 (3) | C61—C60—C58 | 112.2 (2) |
F1—C23—C21 | 112.4 (3) | C59—C60—C58 | 108.9 (2) |
F3—C23—C21 | 112.8 (3) | C61—C60—H60 | 108.1 |
N5—C24—N6 | 129.1 (2) | C59—C60—H60 | 108.1 |
N5—C24—S2 | 119.42 (19) | C58—C60—H60 | 108.1 |
N6—C24—S2 | 111.45 (19) | C60—C61—H61A | 109.5 |
N5—C25—C26 | 120.8 (2) | C60—C61—H61B | 109.5 |
N5—C25—C35 | 116.2 (2) | H61A—C61—H61B | 109.5 |
C26—C25—C35 | 123.1 (2) | C60—C61—H61C | 109.5 |
C25—C26—C27 | 119.1 (2) | H61A—C61—H61C | 109.5 |
C25—C26—C39 | 121.3 (2) | H61B—C61—H61C | 109.5 |
C27—C26—C39 | 119.5 (2) | N11—C62—C49 | 177.7 (3) |
N6—C27—N8 | 120.0 (2) | C64—C63—C68 | 119.2 (2) |
N6—C27—C26 | 119.3 (2) | C64—C63—N12 | 124.5 (2) |
N8—C27—C26 | 120.7 (2) | C68—C63—N12 | 116.3 (2) |
C29—C28—S2 | 114.89 (18) | C65—C64—C63 | 119.8 (2) |
C29—C28—H28A | 108.5 | C65—C64—H64 | 120.1 |
S2—C28—H28A | 108.5 | C63—C64—H64 | 120.1 |
C29—C28—H28B | 108.5 | C64—C65—C66 | 121.4 (2) |
S2—C28—H28B | 108.5 | C64—C65—H65 | 119.3 |
H28A—C28—H28B | 107.5 | C66—C65—H65 | 119.3 |
C30—C29—C34 | 118.4 (3) | C67—C66—C65 | 118.4 (2) |
C30—C29—C28 | 119.3 (2) | C67—C66—H66 | 120.8 |
C34—C29—C28 | 122.3 (2) | C65—C66—H66 | 120.8 |
C31—C30—C29 | 121.6 (3) | C66—C67—C68 | 121.0 (2) |
C31—C30—H30 | 119.2 | C66—C67—C69 | 120.3 (2) |
C29—C30—H30 | 119.2 | C68—C67—C69 | 118.7 (2) |
C32—C31—C30 | 118.9 (3) | C67—C68—C63 | 120.1 (2) |
C32—C31—H31 | 120.5 | C67—C68—H68 | 119.9 |
C30—C31—H31 | 120.5 | C63—C68—H68 | 119.9 |
C31—C32—C33 | 121.6 (3) | F7—C69—F8 | 106.7 (3) |
C31—C32—Cl2 | 119.0 (2) | F7—C69—F9 | 105.5 (3) |
C33—C32—Cl2 | 119.4 (2) | F8—C69—F9 | 105.2 (3) |
C32—C33—C34 | 118.5 (2) | F7—C69—C67 | 113.0 (3) |
C32—C33—H33 | 120.8 | F8—C69—C67 | 113.0 (2) |
C34—C33—H33 | 120.8 | F9—C69—C67 | 112.9 (2) |
C29—C34—C33 | 121.0 (2) | ||
C2—N1—C1—N2 | 0.7 (4) | C31—C32—C33—C34 | 2.9 (4) |
C2—N1—C1—S1 | 179.89 (17) | Cl2—C32—C33—C34 | −177.75 (18) |
C4—N2—C1—N1 | 0.2 (4) | C30—C29—C34—C33 | −1.7 (4) |
C4—N2—C1—S1 | −179.04 (17) | C28—C29—C34—C33 | 177.8 (2) |
C5—S1—C1—N1 | 12.8 (2) | C32—C33—C34—C29 | −1.1 (4) |
C5—S1—C1—N2 | −167.86 (17) | N5—C25—C35—C37 | −68.5 (3) |
C1—N1—C2—C3 | −1.8 (3) | C26—C25—C35—C37 | 111.9 (3) |
C1—N1—C2—C12 | 178.1 (2) | C25—C35—C37—C38 | −65.3 (3) |
N1—C2—C3—C4 | 2.0 (3) | C25—C35—C37—C36 | 170.9 (3) |
C12—C2—C3—C4 | −177.9 (2) | C27—N8—C40—C45 | −154.6 (2) |
N1—C2—C3—C16 | −178.0 (2) | C27—N8—C40—C41 | 27.1 (4) |
C12—C2—C3—C16 | 2.1 (4) | C45—C40—C41—C42 | 1.0 (4) |
C1—N2—C4—N4 | −179.2 (2) | N8—C40—C41—C42 | 179.2 (3) |
C1—N2—C4—C3 | 0.0 (3) | C40—C41—C42—C43 | −0.7 (4) |
C17—N4—C4—N2 | 1.9 (4) | C41—C42—C43—C44 | 0.1 (5) |
C17—N4—C4—C3 | −177.3 (2) | C42—C43—C44—C45 | 0.2 (4) |
C2—C3—C4—N2 | −1.0 (3) | C42—C43—C44—C46 | 177.3 (3) |
C16—C3—C4—N2 | 179.0 (2) | C43—C44—C45—C40 | 0.1 (4) |
C2—C3—C4—N4 | 178.2 (2) | C46—C44—C45—C40 | −177.0 (2) |
C16—C3—C4—N4 | −1.8 (4) | C41—C40—C45—C44 | −0.7 (4) |
C1—S1—C5—C6 | 67.3 (2) | N8—C40—C45—C44 | −179.1 (2) |
S1—C5—C6—C7 | −147.4 (2) | C45—C44—C46—F4 | 80.5 (3) |
S1—C5—C6—C11 | 32.8 (3) | C43—C44—C46—F4 | −96.6 (3) |
C11—C6—C7—C8 | −0.4 (4) | C45—C44—C46—F6 | −38.9 (4) |
C5—C6—C7—C8 | 179.8 (2) | C43—C44—C46—F6 | 143.9 (3) |
C6—C7—C8—C9 | 0.0 (4) | C45—C44—C46—F5 | −159.4 (2) |
C7—C8—C9—C10 | 0.6 (4) | C43—C44—C46—F5 | 23.4 (4) |
C7—C8—C9—Cl1 | 179.5 (2) | C48—N9—C47—N10 | 1.4 (4) |
C8—C9—C10—C11 | −0.7 (4) | C48—N9—C47—S3 | 179.95 (17) |
Cl1—C9—C10—C11 | −179.6 (2) | C50—N10—C47—N9 | 0.1 (4) |
C9—C10—C11—C6 | 0.3 (4) | C50—N10—C47—S3 | −178.53 (16) |
C7—C6—C11—C10 | 0.2 (4) | C51—S3—C47—N9 | 4.5 (2) |
C5—C6—C11—C10 | −180.0 (2) | C51—S3—C47—N10 | −176.72 (17) |
N1—C2—C12—C14 | −55.0 (3) | C47—N9—C48—C49 | −2.4 (3) |
C3—C2—C12—C14 | 124.8 (3) | C47—N9—C48—C58 | 178.7 (2) |
C2—C12—C14—C13 | −50.7 (4) | N9—C48—C49—C50 | 2.0 (4) |
C2—C12—C14—C15 | −178.7 (2) | C58—C48—C49—C50 | −179.1 (2) |
C4—N4—C17—C22 | 167.8 (2) | N9—C48—C49—C62 | −176.8 (2) |
C4—N4—C17—C18 | −12.9 (4) | C58—C48—C49—C62 | 2.1 (4) |
C22—C17—C18—C19 | −1.6 (4) | C47—N10—C50—N12 | 179.8 (2) |
N4—C17—C18—C19 | 179.1 (3) | C47—N10—C50—C49 | −0.6 (3) |
C17—C18—C19—C20 | 1.0 (5) | C63—N12—C50—N10 | −2.6 (4) |
C18—C19—C20—C21 | 0.1 (5) | C63—N12—C50—C49 | 177.8 (2) |
C19—C20—C21—C22 | −0.4 (5) | C48—C49—C50—N10 | −0.4 (3) |
C19—C20—C21—C23 | 175.9 (3) | C62—C49—C50—N10 | 178.4 (2) |
C20—C21—C22—C17 | −0.3 (4) | C48—C49—C50—N12 | 179.2 (2) |
C23—C21—C22—C17 | −176.7 (3) | C62—C49—C50—N12 | −2.0 (3) |
C18—C17—C22—C21 | 1.3 (4) | C47—S3—C51—C52 | 74.5 (2) |
N4—C17—C22—C21 | −179.4 (2) | S3—C51—C52—C53 | −138.2 (2) |
C22—C21—C23—F2 | −152.7 (3) | S3—C51—C52—C57 | 42.9 (3) |
C20—C21—C23—F2 | 30.9 (4) | C57—C52—C53—C54 | −0.5 (4) |
C22—C21—C23—F1 | 85.8 (4) | C51—C52—C53—C54 | −179.5 (2) |
C20—C21—C23—F1 | −90.6 (4) | C52—C53—C54—C55 | −0.7 (4) |
C22—C21—C23—F3 | −33.1 (4) | C53—C54—C55—C56 | 1.6 (4) |
C20—C21—C23—F3 | 150.5 (3) | C53—C54—C55—Cl3 | −178.3 (2) |
C25—N5—C24—N6 | 2.4 (4) | C54—C55—C56—C57 | −1.3 (4) |
C25—N5—C24—S2 | −178.31 (17) | Cl3—C55—C56—C57 | 178.60 (19) |
C27—N6—C24—N5 | −3.0 (4) | C53—C52—C57—C56 | 0.9 (4) |
C27—N6—C24—S2 | 177.71 (17) | C51—C52—C57—C56 | 179.8 (2) |
C28—S2—C24—N5 | 11.2 (2) | C55—C56—C57—C52 | 0.0 (4) |
C28—S2—C24—N6 | −169.36 (18) | N9—C48—C58—C60 | −44.6 (3) |
C24—N5—C25—C26 | 1.4 (3) | C49—C48—C58—C60 | 136.5 (3) |
C24—N5—C25—C35 | −178.2 (2) | C48—C58—C60—C61 | −54.3 (3) |
N5—C25—C26—C27 | −4.2 (4) | C48—C58—C60—C59 | −177.9 (2) |
C35—C25—C26—C27 | 175.4 (2) | C50—N12—C63—C64 | 16.2 (4) |
N5—C25—C26—C39 | 177.9 (2) | C50—N12—C63—C68 | −165.5 (2) |
C35—C25—C26—C39 | −2.5 (4) | C68—C63—C64—C65 | 0.8 (4) |
C24—N6—C27—N8 | 179.9 (2) | N12—C63—C64—C65 | 179.1 (2) |
C24—N6—C27—C26 | −0.3 (3) | C63—C64—C65—C66 | −0.4 (4) |
C40—N8—C27—N6 | −6.2 (4) | C64—C65—C66—C67 | −0.6 (4) |
C40—N8—C27—C26 | 174.0 (2) | C65—C66—C67—C68 | 1.2 (4) |
C25—C26—C27—N6 | 3.6 (3) | C65—C66—C67—C69 | 179.7 (3) |
C39—C26—C27—N6 | −178.5 (2) | C66—C67—C68—C63 | −0.7 (4) |
C25—C26—C27—N8 | −176.5 (2) | C69—C67—C68—C63 | −179.3 (2) |
C39—C26—C27—N8 | 1.3 (4) | C64—C63—C68—C67 | −0.3 (4) |
C24—S2—C28—C29 | 71.8 (2) | N12—C63—C68—C67 | −178.8 (2) |
S2—C28—C29—C30 | −126.3 (2) | C66—C67—C69—F7 | −104.6 (3) |
S2—C28—C29—C34 | 54.1 (3) | C68—C67—C69—F7 | 74.0 (4) |
C34—C29—C30—C31 | 3.0 (4) | C66—C67—C69—F8 | 16.6 (4) |
C28—C29—C30—C31 | −176.6 (3) | C68—C67—C69—F8 | −164.8 (3) |
C29—C30—C31—C32 | −1.3 (5) | C66—C67—C69—F9 | 135.8 (3) |
C30—C31—C32—C33 | −1.7 (4) | C68—C67—C69—F9 | −45.6 (4) |
C30—C31—C32—Cl2 | 178.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4n···N7i | 0.88 | 2.39 | 3.227 (3) | 159 |
N8—H8n···N3i | 0.88 | 2.38 | 3.213 (3) | 158 |
N12—H12n···N11ii | 0.88 | 2.36 | 3.206 (3) | 160 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C23H20ClF3N4S |
Mr | 476.94 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 15.3906 (6), 15.7040 (7), 15.9129 (7) |
α, β, γ (°) | 89.568 (3), 74.825 (4), 62.980 (4) |
V (Å3) | 3278.9 (2) |
Z | 6 |
Radiation type | Cu Kα |
µ (mm−1) | 2.83 |
Crystal size (mm) | 0.35 × 0.15 × 0.03 |
Data collection | |
Diffractometer | Agilent SuperNova Dual diffractometer with Atlas detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2011) |
Tmin, Tmax | 0.437, 0.920 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 38203, 25266, 18393 |
Rint | 0.075 |
(sin θ/λ)max (Å−1) | 0.632 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.190, 1.02 |
No. of reflections | 25266 |
No. of parameters | 866 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.44, −0.53 |
Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and QMol (Gans & Shalloway, 2001), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4n···N7i | 0.88 | 2.39 | 3.227 (3) | 159 |
N8—H8n···N3i | 0.88 | 2.38 | 3.213 (3) | 158 |
N12—H12n···N11ii | 0.88 | 2.36 | 3.206 (3) | 160 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y+1, −z. |
Footnotes
‡Additional correspondence author, e-mail: elemam5@hotmail.com.
Acknowledgements
The financial support of the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, is greatly appreciated. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).
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The chemotherapeutic efficacy of pyrimidine derivatives is related to their ability to inhibit vital enzymes responsible for DNA bio-synthesis. Thus, several pyrimidine non-nucleoside derivatives are known to exhibit anti-cancer (Al-Safarjalani et al., 2005), anti-viral (Brunelle et al., 2007; Ding et al., 2006) and anti-bacterial activities (Al-Abdullah et al., 2011). In continuation to our interest in the chemical and pharmacological properties of pyrimidine derivatives (Al-Omar et al., 2010; El-Emam et al. 2011), we synthesized the title compound (I) as potential a chemotherapeutic agent.
In (I), Fig. 1, three independent molecules comprise the asymmetric unit, and these have very similar molecular conformations as seen in the overlay diagram, Fig. 2. With respect to the pyrimidinyl ring, the chlorobenzene and CF3-benzene rings form dihedral angles of 80.36 (13) and 11.89 (14)°, respectively, for the N1-containing molecule; the dihedral angle between the benzene rings is 69.50 (14)°. For the N5-containing molecule the dihedral angles are 88.07 (14), 23.30 (14) and 64.81 (16), respectively, and for the N9-containing molecule, the angles are 85.94 (14), 13.81 (14) and 72.16 (15)°, respectively. In each case, the 2-methylpropyl group is orientated in the same direction as the chlorobenzene ring.
In the crystal structure, the N1- and N5-containing molecules associate to form a two molecule aggregate via N—H···N(cyano) hydrogen bonds and 12-membered {···HNC3N}2 synthons, Table 1 and Fig. 3. The N3-containing molecules self-associate similarly but over a centre of inversion, Table 1.