Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037786/hg2273sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037786/hg2273Isup2.hkl |
CCDC reference: 657434
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.037
- wR factor = 0.092
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.52 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.04 Ratio PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. CL1 .. 2.91 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.38 From the CIF: _reflns_number_total 4177 Count of symmetry unique reflns 2388 Completeness (_total/calc) 174.92% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1789 Fraction of Friedel pairs measured 0.749 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Bloxham et al. (2006); Borchardt et al. (2005); Hermann et al. (2003); Radwan & El-Sherbiny (2007); Ulrich (2004).
The title compound was synthesized by by the reaction of 2,4-dichlorobenzaldehyde, 1-phenylguanidinium hydrogencarbonate and ethyl 4,4,4-trifluoro-3-oxobutanoate in 1:1:1 molar ratio in solid state catalyzed by sulfamic acid at 363 K. After cooling, the reaction mixture was washed with water and recrystallized from ethanol, which gave single crystals suitable for X-ray diffraction.
The hydrogen atoms bonded to nitrogen atom was positioned from a Fourier difference map and were refined freely. Other H atoms were placed in calculated positions, with C—H = 0.93, 0.96, 0.97 or 0.98 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(parent atom).
The derivatives of pyrimidine are reported to have various biological activities, such as antitumor (Radwan & El-Sherbiny, 2007), CB1 cannabinoid receptor modulatory (Bloxham et al., 2006) and hepatitis C virus RNA-dependent RNA polymerase inhibitory (Borchardt et al., 2005). In addition, compounds that contain fluorine have special bioactivity, for example, flumioxazin is a widely used herbicide (Hermann et al., 2003; Ulrich,2004). This led us to pay attention to the synthesis and structure of these fluoro-compounds and have synthesized aseries of derivatives of dihydropyrimidines. Here we report the crystal structure of the title compound, (I).
The molecular structure of (I) is shown in Fig. 1. The dihedral angle between plane N1/N2/C8/C9 and phenyl plane C1—C6, is 87.90 (8)°, which shows the two planes are nearly perpendicular. The atoms C7 and C10 deviate from the plane N1/N2/C8/C9 by 0.574 (4) Å and 0.157 (4) Å in the same direction, which shows the pyrimiding ring adopts a twist boat conformation. The connection of the pyrimidine ring and phenyl ring C15—C20 can be described as the torsion angle of C15—N3—C8—N1, -173.7 (2)°. In the structure, the crystal packing is stabilized intermolecular hydrogen bonds: N3—H3A···O1, N1—H1A···O1 and intramolecular hydrogen bond: N1—H1A···Cl1 (Fig.2 & Table 2).
For related literature, see: Bloxham et al. (2006); Borchardt et al. (2005); Hermann et al. (2003); Radwan & El-Sherbiny (2007); Ulrich (2004).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C20H16Cl2F3N3O2 | F(000) = 936 |
Mr = 458.26 | Dx = 1.481 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4124 reflections |
a = 11.0085 (15) Å | θ = 2.2–25.1° |
b = 11.8934 (17) Å | µ = 0.37 mm−1 |
c = 15.698 (2) Å | T = 294 K |
V = 2055.4 (5) Å3 | Block, colourless |
Z = 4 | 0.26 × 0.24 × 0.20 mm |
Bruker SMART CCD area-detector diffractometer | 4177 independent reflections |
Radiation source: fine-focus sealed tube | 3175 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 26.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→13 |
Tmin = 0.911, Tmax = 0.931 | k = −14→14 |
11861 measured reflections | l = −19→19 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0404P)2 + 0.3148P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.092 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.21 e Å−3 |
4177 reflections | Δρmin = −0.22 e Å−3 |
281 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.0261 (15) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.06 (6) |
C20H16Cl2F3N3O2 | V = 2055.4 (5) Å3 |
Mr = 458.26 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 11.0085 (15) Å | µ = 0.37 mm−1 |
b = 11.8934 (17) Å | T = 294 K |
c = 15.698 (2) Å | 0.26 × 0.24 × 0.20 mm |
Bruker SMART CCD area-detector diffractometer | 4177 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3175 reflections with I > 2σ(I) |
Tmin = 0.911, Tmax = 0.931 | Rint = 0.038 |
11861 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.092 | Δρmax = 0.21 e Å−3 |
S = 1.04 | Δρmin = −0.22 e Å−3 |
4177 reflections | Absolute structure: Flack (1983) |
281 parameters | Absolute structure parameter: −0.06 (6) |
2 restraints |
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 | 0.72705 (8) | 0.14863 (7) | −0.12933 (5) | 0.0766 (3) | |
Cl2 | 0.37002 (8) | 0.42819 (9) | −0.22290 (5) | 0.0887 (3) | |
F1 | 0.62596 (16) | 0.48924 (14) | 0.24705 (10) | 0.0706 (5) | |
F2 | 0.80585 (16) | 0.45551 (14) | 0.29272 (9) | 0.0730 (5) | |
F3 | 0.77062 (17) | 0.60034 (12) | 0.21670 (10) | 0.0757 (5) | |
O1 | 0.56257 (18) | 0.19540 (17) | 0.14384 (13) | 0.0646 (5) | |
O2 | 0.64809 (17) | 0.27081 (15) | 0.25945 (11) | 0.0592 (5) | |
N1 | 0.86238 (17) | 0.32244 (16) | 0.00923 (13) | 0.0432 (5) | |
N2 | 0.85306 (18) | 0.48302 (16) | 0.09472 (12) | 0.0428 (5) | |
N3 | 0.9898 (2) | 0.47054 (18) | −0.01780 (15) | 0.0528 (5) | |
C1 | 0.6315 (2) | 0.2608 (2) | −0.10509 (15) | 0.0456 (6) | |
C2 | 0.5460 (2) | 0.2923 (3) | −0.16446 (15) | 0.0540 (7) | |
H2 | 0.5375 | 0.2527 | −0.2152 | 0.065* | |
C3 | 0.4732 (2) | 0.3837 (2) | −0.14692 (16) | 0.0525 (7) | |
C4 | 0.4828 (2) | 0.4401 (2) | −0.07171 (17) | 0.0521 (7) | |
H4 | 0.4322 | 0.5008 | −0.0601 | 0.063* | |
C5 | 0.5684 (2) | 0.4060 (2) | −0.01277 (16) | 0.0461 (6) | |
H5 | 0.5744 | 0.4446 | 0.0386 | 0.055* | |
C6 | 0.6455 (2) | 0.31641 (18) | −0.02757 (14) | 0.0381 (5) | |
C7 | 0.7429 (2) | 0.28239 (17) | 0.03625 (14) | 0.0393 (5) | |
H7 | 0.7453 | 0.2001 | 0.0388 | 0.047* | |
C8 | 0.89924 (19) | 0.42730 (19) | 0.03061 (16) | 0.0408 (6) | |
C9 | 0.7726 (2) | 0.42650 (18) | 0.14511 (14) | 0.0379 (5) | |
C10 | 0.7207 (2) | 0.32622 (17) | 0.12503 (14) | 0.0388 (5) | |
C11 | 0.6358 (2) | 0.2590 (2) | 0.17605 (16) | 0.0450 (6) | |
C12 | 0.5585 (3) | 0.2171 (3) | 0.3156 (2) | 0.0770 (10) | |
H12A | 0.5411 | 0.2663 | 0.3633 | 0.092* | |
H12B | 0.4835 | 0.2051 | 0.2845 | 0.092* | |
C13 | 0.6041 (3) | 0.1095 (3) | 0.3472 (2) | 0.0955 (12) | |
H13A | 0.6823 | 0.1203 | 0.3731 | 0.143* | |
H13B | 0.6114 | 0.0576 | 0.3006 | 0.143* | |
H13C | 0.5486 | 0.0798 | 0.3887 | 0.143* | |
C14 | 0.7432 (3) | 0.4921 (2) | 0.22603 (15) | 0.0491 (6) | |
C15 | 1.0562 (2) | 0.5710 (2) | −0.00892 (18) | 0.0513 (7) | |
C16 | 1.1471 (3) | 0.5888 (3) | −0.0697 (2) | 0.0690 (8) | |
H16 | 1.1620 | 0.5345 | −0.1111 | 0.083* | |
C17 | 1.2143 (3) | 0.6858 (3) | −0.0688 (3) | 0.0866 (11) | |
H17 | 1.2739 | 0.6971 | −0.1099 | 0.104* | |
C18 | 1.1946 (3) | 0.7664 (3) | −0.0077 (3) | 0.0902 (12) | |
H18 | 1.2402 | 0.8322 | −0.0074 | 0.108* | |
C20 | 1.0364 (3) | 0.6516 (2) | 0.05281 (19) | 0.0606 (7) | |
H20 | 0.9767 | 0.6411 | 0.0940 | 0.073* | |
C19 | 1.1066 (3) | 0.7487 (3) | 0.0527 (2) | 0.0779 (10) | |
H19 | 1.0937 | 0.8028 | 0.0945 | 0.093* | |
H1A | 0.897 (2) | 0.290 (2) | −0.0361 (11) | 0.055 (8)* | |
H3A | 1.016 (3) | 0.426 (2) | −0.0595 (13) | 0.067 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0825 (6) | 0.0701 (5) | 0.0772 (5) | 0.0141 (4) | −0.0005 (4) | −0.0343 (4) |
Cl2 | 0.0660 (5) | 0.1399 (8) | 0.0603 (4) | 0.0033 (5) | −0.0208 (4) | 0.0215 (5) |
F1 | 0.0622 (10) | 0.0738 (10) | 0.0758 (10) | 0.0072 (9) | 0.0117 (9) | −0.0183 (9) |
F2 | 0.0878 (12) | 0.0810 (12) | 0.0503 (9) | −0.0055 (9) | −0.0245 (9) | 0.0008 (8) |
F3 | 0.1199 (15) | 0.0432 (9) | 0.0639 (9) | −0.0128 (9) | 0.0036 (10) | −0.0139 (7) |
O1 | 0.0591 (11) | 0.0644 (12) | 0.0704 (12) | −0.0280 (10) | −0.0031 (10) | −0.0053 (10) |
O2 | 0.0630 (12) | 0.0649 (11) | 0.0497 (11) | −0.0154 (10) | 0.0075 (9) | 0.0041 (9) |
N1 | 0.0335 (10) | 0.0393 (11) | 0.0568 (12) | 0.0029 (9) | 0.0029 (10) | −0.0072 (9) |
N2 | 0.0418 (11) | 0.0368 (10) | 0.0499 (11) | −0.0042 (9) | −0.0017 (10) | 0.0003 (9) |
N3 | 0.0450 (12) | 0.0474 (12) | 0.0660 (14) | −0.0032 (10) | 0.0115 (11) | 0.0005 (12) |
C1 | 0.0404 (13) | 0.0477 (14) | 0.0488 (14) | −0.0079 (12) | 0.0067 (12) | −0.0073 (11) |
C2 | 0.0519 (15) | 0.0739 (19) | 0.0362 (13) | −0.0195 (14) | 0.0008 (12) | −0.0049 (13) |
C3 | 0.0377 (14) | 0.0736 (19) | 0.0462 (14) | −0.0114 (14) | −0.0033 (12) | 0.0143 (13) |
C4 | 0.0422 (15) | 0.0557 (16) | 0.0585 (16) | 0.0053 (12) | −0.0050 (13) | 0.0061 (13) |
C5 | 0.0419 (14) | 0.0479 (14) | 0.0485 (14) | 0.0031 (11) | −0.0052 (12) | −0.0039 (12) |
C6 | 0.0339 (12) | 0.0358 (11) | 0.0447 (12) | −0.0077 (10) | −0.0001 (11) | −0.0020 (10) |
C7 | 0.0387 (13) | 0.0302 (10) | 0.0491 (13) | −0.0041 (10) | −0.0007 (11) | −0.0026 (9) |
C8 | 0.0320 (12) | 0.0362 (12) | 0.0543 (14) | 0.0048 (10) | −0.0052 (11) | 0.0048 (11) |
C9 | 0.0333 (11) | 0.0379 (12) | 0.0426 (12) | 0.0021 (10) | −0.0081 (10) | 0.0012 (10) |
C10 | 0.0344 (12) | 0.0368 (12) | 0.0452 (13) | −0.0008 (10) | −0.0050 (11) | 0.0017 (10) |
C11 | 0.0398 (13) | 0.0409 (13) | 0.0543 (15) | −0.0029 (12) | −0.0013 (13) | −0.0011 (11) |
C12 | 0.068 (2) | 0.088 (2) | 0.075 (2) | −0.0070 (18) | 0.0274 (17) | 0.0051 (18) |
C13 | 0.087 (3) | 0.105 (3) | 0.094 (3) | −0.026 (2) | 0.006 (2) | 0.039 (2) |
C14 | 0.0558 (16) | 0.0458 (13) | 0.0458 (13) | −0.0053 (12) | −0.0067 (13) | −0.0042 (11) |
C15 | 0.0347 (13) | 0.0478 (15) | 0.0715 (17) | −0.0023 (11) | −0.0003 (12) | 0.0149 (14) |
C16 | 0.0518 (17) | 0.0627 (18) | 0.093 (2) | 0.0006 (15) | 0.0132 (17) | 0.0147 (16) |
C17 | 0.059 (2) | 0.074 (2) | 0.127 (3) | −0.0135 (19) | 0.013 (2) | 0.035 (2) |
C18 | 0.065 (2) | 0.062 (2) | 0.144 (4) | −0.0248 (17) | −0.014 (2) | 0.030 (2) |
C20 | 0.0530 (17) | 0.0531 (17) | 0.0757 (19) | −0.0118 (14) | −0.0026 (14) | 0.0083 (15) |
C19 | 0.073 (2) | 0.0538 (18) | 0.107 (3) | −0.0164 (17) | −0.005 (2) | 0.0039 (18) |
Cl1—C1 | 1.741 (3) | C5—H5 | 0.9300 |
Cl2—C3 | 1.730 (3) | C6—C7 | 1.522 (3) |
F1—C14 | 1.333 (3) | C7—C10 | 1.508 (3) |
F2—C14 | 1.327 (3) | C7—H7 | 0.9800 |
F3—C14 | 1.330 (3) | C9—C10 | 1.360 (3) |
O1—C11 | 1.215 (3) | C9—C14 | 1.526 (3) |
O2—C11 | 1.324 (3) | C10—C11 | 1.468 (3) |
O2—C12 | 1.469 (3) | C12—C13 | 1.462 (5) |
N1—C8 | 1.354 (3) | C12—H12A | 0.9700 |
N1—C7 | 1.462 (3) | C12—H12B | 0.9700 |
N1—H1A | 0.897 (10) | C13—H13A | 0.9600 |
N2—C8 | 1.308 (3) | C13—H13B | 0.9600 |
N2—C9 | 1.365 (3) | C13—H13C | 0.9600 |
N3—C8 | 1.355 (3) | C15—C20 | 1.381 (4) |
N3—C15 | 1.408 (3) | C15—C16 | 1.399 (4) |
N3—H3A | 0.890 (10) | C16—C17 | 1.371 (4) |
C1—C2 | 1.377 (4) | C16—H16 | 0.9300 |
C1—C6 | 1.393 (3) | C17—C18 | 1.373 (5) |
C2—C3 | 1.379 (4) | C17—H17 | 0.9300 |
C2—H2 | 0.9300 | C18—C19 | 1.373 (5) |
C3—C4 | 1.362 (4) | C18—H18 | 0.9300 |
C4—C5 | 1.382 (3) | C20—C19 | 1.389 (4) |
C4—H4 | 0.9300 | C20—H20 | 0.9300 |
C5—C6 | 1.381 (3) | C19—H19 | 0.9300 |
C11—O2—C12 | 118.6 (2) | C11—C10—C7 | 114.78 (19) |
C8—N1—C7 | 119.86 (19) | O1—C11—O2 | 123.1 (2) |
C8—N1—H1A | 117.8 (17) | O1—C11—C10 | 122.3 (2) |
C7—N1—H1A | 118.4 (17) | O2—C11—C10 | 114.6 (2) |
C8—N2—C9 | 116.66 (19) | C13—C12—O2 | 110.7 (3) |
C8—N3—C15 | 130.5 (2) | C13—C12—H12A | 109.5 |
C8—N3—H3A | 115.5 (19) | O2—C12—H12A | 109.5 |
C15—N3—H3A | 113.9 (19) | C13—C12—H12B | 109.5 |
C2—C1—C6 | 122.5 (2) | O2—C12—H12B | 109.5 |
C2—C1—Cl1 | 118.25 (19) | H12A—C12—H12B | 108.1 |
C6—C1—Cl1 | 119.21 (19) | C12—C13—H13A | 109.5 |
C1—C2—C3 | 118.5 (2) | C12—C13—H13B | 109.5 |
C1—C2—H2 | 120.8 | H13A—C13—H13B | 109.5 |
C3—C2—H2 | 120.8 | C12—C13—H13C | 109.5 |
C4—C3—C2 | 121.1 (2) | H13A—C13—H13C | 109.5 |
C4—C3—Cl2 | 119.9 (2) | H13B—C13—H13C | 109.5 |
C2—C3—Cl2 | 119.0 (2) | F2—C14—F3 | 106.7 (2) |
C3—C4—C5 | 119.3 (2) | F2—C14—F1 | 107.4 (2) |
C3—C4—H4 | 120.4 | F3—C14—F1 | 105.8 (2) |
C5—C4—H4 | 120.4 | F2—C14—C9 | 112.3 (2) |
C6—C5—C4 | 122.2 (2) | F3—C14—C9 | 110.8 (2) |
C6—C5—H5 | 118.9 | F1—C14—C9 | 113.5 (2) |
C4—C5—H5 | 118.9 | C20—C15—C16 | 119.1 (3) |
C5—C6—C1 | 116.4 (2) | C20—C15—N3 | 125.2 (2) |
C5—C6—C7 | 121.8 (2) | C16—C15—N3 | 115.6 (3) |
C1—C6—C7 | 121.8 (2) | C17—C16—C15 | 120.4 (3) |
N1—C7—C10 | 107.54 (18) | C17—C16—H16 | 119.8 |
N1—C7—C6 | 110.87 (18) | C15—C16—H16 | 119.8 |
C10—C7—C6 | 113.73 (19) | C16—C17—C18 | 120.7 (3) |
N1—C7—H7 | 108.2 | C16—C17—H17 | 119.7 |
C10—C7—H7 | 108.2 | C18—C17—H17 | 119.7 |
C6—C7—H7 | 108.2 | C19—C18—C17 | 119.1 (3) |
N2—C8—N1 | 122.8 (2) | C19—C18—H18 | 120.4 |
N2—C8—N3 | 121.7 (2) | C17—C18—H18 | 120.4 |
N1—C8—N3 | 115.5 (2) | C15—C20—C19 | 119.3 (3) |
C10—C9—N2 | 124.8 (2) | C15—C20—H20 | 120.4 |
C10—C9—C14 | 123.6 (2) | C19—C20—H20 | 120.4 |
N2—C9—C14 | 111.61 (19) | C18—C19—C20 | 121.4 (3) |
C9—C10—C11 | 128.3 (2) | C18—C19—H19 | 119.3 |
C9—C10—C7 | 116.7 (2) | C20—C19—H19 | 119.3 |
C6—C1—C2—C3 | 1.4 (4) | N2—C9—C10—C7 | −7.6 (3) |
Cl1—C1—C2—C3 | −177.60 (19) | C14—C9—C10—C7 | 169.7 (2) |
C1—C2—C3—C4 | −1.9 (4) | N1—C7—C10—C9 | 30.7 (3) |
C1—C2—C3—Cl2 | 177.07 (19) | C6—C7—C10—C9 | −92.4 (2) |
C2—C3—C4—C5 | 1.1 (4) | N1—C7—C10—C11 | −154.66 (19) |
Cl2—C3—C4—C5 | −177.8 (2) | C6—C7—C10—C11 | 82.2 (2) |
C3—C4—C5—C6 | 0.2 (4) | C12—O2—C11—O1 | −8.8 (4) |
C4—C5—C6—C1 | −0.7 (3) | C12—O2—C11—C10 | 173.1 (2) |
C4—C5—C6—C7 | 177.5 (2) | C9—C10—C11—O1 | 152.8 (3) |
C2—C1—C6—C5 | −0.1 (3) | C7—C10—C11—O1 | −21.1 (3) |
Cl1—C1—C6—C5 | 178.86 (18) | C9—C10—C11—O2 | −29.1 (3) |
C2—C1—C6—C7 | −178.3 (2) | C7—C10—C11—O2 | 157.0 (2) |
Cl1—C1—C6—C7 | 0.6 (3) | C11—O2—C12—C13 | 97.6 (3) |
C8—N1—C7—C10 | −38.3 (3) | C10—C9—C14—F2 | 82.9 (3) |
C8—N1—C7—C6 | 86.6 (2) | N2—C9—C14—F2 | −99.5 (2) |
C5—C6—C7—N1 | −101.8 (3) | C10—C9—C14—F3 | −158.0 (2) |
C1—C6—C7—N1 | 76.4 (3) | N2—C9—C14—F3 | 19.6 (3) |
C5—C6—C7—C10 | 19.5 (3) | C10—C9—C14—F1 | −39.2 (3) |
C1—C6—C7—C10 | −162.3 (2) | N2—C9—C14—F1 | 138.4 (2) |
C9—N2—C8—N1 | 6.0 (3) | C8—N3—C15—C20 | −3.2 (4) |
C9—N2—C8—N3 | −172.5 (2) | C8—N3—C15—C16 | 178.3 (3) |
C7—N1—C8—N2 | 21.8 (3) | C20—C15—C16—C17 | −1.0 (4) |
C7—N1—C8—N3 | −159.7 (2) | N3—C15—C16—C17 | 177.7 (3) |
C15—N3—C8—N2 | 4.9 (4) | C15—C16—C17—C18 | 0.7 (5) |
C15—N3—C8—N1 | −173.7 (2) | C16—C17—C18—C19 | 0.2 (6) |
C8—N2—C9—C10 | −12.8 (3) | C16—C15—C20—C19 | 0.4 (4) |
C8—N2—C9—C14 | 169.6 (2) | N3—C15—C20—C19 | −178.1 (3) |
N2—C9—C10—C11 | 178.6 (2) | C17—C18—C19—C20 | −0.7 (5) |
C14—C9—C10—C11 | −4.1 (4) | C15—C20—C19—C18 | 0.4 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O1i | 0.89 (1) | 2.03 (1) | 2.907 (3) | 170 (3) |
N1—H1A···O1i | 0.90 (1) | 2.49 (2) | 3.267 (3) | 145 (2) |
N1—H1A···Cl1 | 0.90 (1) | 2.91 (2) | 3.350 (2) | 112 (2) |
Symmetry code: (i) x+1/2, −y+1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C20H16Cl2F3N3O2 |
Mr | 458.26 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 294 |
a, b, c (Å) | 11.0085 (15), 11.8934 (17), 15.698 (2) |
V (Å3) | 2055.4 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.37 |
Crystal size (mm) | 0.26 × 0.24 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.911, 0.931 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11861, 4177, 3175 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.092, 1.04 |
No. of reflections | 4177 |
No. of parameters | 281 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.22 |
Absolute structure | Flack (1983) |
Absolute structure parameter | −0.06 (6) |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O1i | 0.890 (10) | 2.026 (12) | 2.907 (3) | 170 (3) |
N1—H1A···O1i | 0.897 (10) | 2.490 (17) | 3.267 (3) | 145 (2) |
N1—H1A···Cl1 | 0.897 (10) | 2.91 (2) | 3.350 (2) | 111.8 (18) |
Symmetry code: (i) x+1/2, −y+1/2, −z. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
The derivatives of pyrimidine are reported to have various biological activities, such as antitumor (Radwan & El-Sherbiny, 2007), CB1 cannabinoid receptor modulatory (Bloxham et al., 2006) and hepatitis C virus RNA-dependent RNA polymerase inhibitory (Borchardt et al., 2005). In addition, compounds that contain fluorine have special bioactivity, for example, flumioxazin is a widely used herbicide (Hermann et al., 2003; Ulrich,2004). This led us to pay attention to the synthesis and structure of these fluoro-compounds and have synthesized aseries of derivatives of dihydropyrimidines. Here we report the crystal structure of the title compound, (I).
The molecular structure of (I) is shown in Fig. 1. The dihedral angle between plane N1/N2/C8/C9 and phenyl plane C1—C6, is 87.90 (8)°, which shows the two planes are nearly perpendicular. The atoms C7 and C10 deviate from the plane N1/N2/C8/C9 by 0.574 (4) Å and 0.157 (4) Å in the same direction, which shows the pyrimiding ring adopts a twist boat conformation. The connection of the pyrimidine ring and phenyl ring C15—C20 can be described as the torsion angle of C15—N3—C8—N1, -173.7 (2)°. In the structure, the crystal packing is stabilized intermolecular hydrogen bonds: N3—H3A···O1, N1—H1A···O1 and intramolecular hydrogen bond: N1—H1A···Cl1 (Fig.2 & Table 2).