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Methyl 4-(4-fluoro­phen­yl)-6-methyl-2-oxo-1,2,3,4-tetra­hydro­pyrimidine-5-car­box­yl­ate, (I), was found to exhibit solvato­morphism. The compound was pre­pared using a classic Biginelli reaction under mild conditions, without using catalysts and in a solvent-free environment. Single crystals of two solvato­morphs and one anhydrous form of (I) were obtained through various crystallization methods. The anhydrous form, C13H13FN2O3, was found to crystallize in the monoclinic space group C2/c. It showed one mol­ecule in the asymmetric unit. The solvato­morph with included carbon tetra­chloride, C13H13FN2O3·0.25CCl4, was found to crystallize in the monoclinic space group P2/n. The asymmetric unit revealed two mol­ecules of (I) and one disordered carbon tetra­chloride solvent mol­ecule that lies on a twofold axis. A solvato­morph including ethyl acetate, C13H13FN2O3·0.5C4H8O2, was found to crystallize in the triclinic space group P\overline{1} with one mol­ecule of (I) and one solvent molecule on an inversion centre in the asymmetric unit. The solvent mol­ecules in the solvato­morphs were found to be disordered, with a unique case of crystallographically induced disorder in (I) crystallized with ethyl acetate. Hydrogen-bonding inter­actions, for example, N—H...O=C, C—H...O=C, C—H...F and C—H...π, contribute to the crystal packing with the formation of a characteristic dimer through N—H...O=C inter­actions in all three forms. The solvato­morphs display additional inter­actions, such as C—F...N and C—Cl...π, which are responsible for their mol­ecular arrangement. The thermal properties of the forms were analysed through differential scanning calorimetry (DSC), hot stage microscopy (HSM) and thermogravimetric analysis (TGA) experiments.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620009560/cu3165sup1.cif
Contains datablocks F1, S1, S2, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009560/cu3165F1sup2.hkl
Contains datablock F1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009560/cu3165S1sup3.hkl
Contains datablock S1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009560/cu3165S2sup4.hkl
Contains datablock S2

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229620009560/cu3165sup5.pdf
Additional geometry details

CCDC references: 1919255; 1919257; 1919259

Computing details top

For all structures, data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and SIR2014 (Burla et al., 2015); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015) and WinGX (Farrugia (2012); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2020) and PARST (Nardelli, 1995).

Methyl 4-(4-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (F1) top
Crystal data top
C13H13FN2O3F(000) = 1104
Mr = 264.25Dx = 1.382 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 16.0881 (15) ÅCell parameters from 7891 reflections
b = 7.1958 (8) Åθ = 2.7–29.9°
c = 23.177 (3) ŵ = 0.11 mm1
β = 108.838 (4)°T = 90 K
V = 2539.4 (5) Å3Plate, colourless
Z = 80.40 × 0.25 × 0.09 mm
Data collection top
Bruker APEXII CCD
diffractometer
2706 reflections with I > 2σ(I)
φ and ω scansRint = 0.072
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
θmax = 30.1°, θmin = 2.7°
Tmin = 0.647, Tmax = 0.746h = 2222
24306 measured reflectionsk = 910
3737 independent reflectionsl = 3232
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0511P)2 + 1.7817P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3737 reflectionsΔρmax = 0.39 e Å3
182 parametersΔρmin = 0.26 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. SCXRD data of all single crystals of (I) were collected on a Bruker AXS SMART APEX CCD diffractometer using Mo Kα radiation (λ = 0.71073 Å) at 100 (2) K. Unit cell measurement, data collection, integration, scaling and absorption correction were performed using Bruker Apex II software and SAINT suite of programs were used for data reduction (Bruker, 2012). Scaling and absorption correction was performed using SADABAS software (Bruker, 2001). Crystal structures were solved using direct methods by SIR 2014 program (Burla et al., 2015) and refined using full matrix least squares method by SHELXL 2014 (Sheldrick, 2015) embedded in the WinGX program suite (Version 2014.1). Geometrical calculations were performed using PLATON (Spek, 2020) and PARST (Nardelli, 1995). Anisotropic refinement was performed for all non-hydrogen atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.02856 (6)0.28689 (14)0.08155 (5)0.0212 (2)
O20.04829 (6)0.08374 (13)0.11713 (4)0.0183 (2)
O30.19561 (6)0.43566 (13)0.02354 (4)0.0159 (2)
F10.42399 (6)0.14688 (16)0.28731 (4)0.0366 (3)
N10.09065 (7)0.34590 (17)0.06405 (5)0.0128 (2)
H1A0.0744 (10)0.464 (3)0.0647 (7)0.020 (4)*
N20.17380 (7)0.12694 (16)0.03515 (5)0.0126 (2)
H2A0.2153 (11)0.100 (2)0.0197 (8)0.022 (4)*
C10.27321 (9)0.2129 (2)0.13482 (6)0.0173 (3)
H10.2630820.2974930.1017880.021*
C20.34316 (9)0.2433 (2)0.18837 (7)0.0229 (3)
H20.3812190.3468390.1921470.027*
C30.35521 (9)0.1195 (2)0.23523 (6)0.0233 (3)
C40.30157 (9)0.0309 (2)0.23263 (6)0.0231 (3)
H40.3113580.1127700.2663340.028*
C50.23225 (9)0.0593 (2)0.17878 (6)0.0190 (3)
H50.1938810.1619170.1757220.023*
C60.21849 (8)0.06081 (19)0.12938 (5)0.0129 (3)
C70.14667 (8)0.02117 (18)0.06901 (5)0.0112 (2)
H70.1369800.1368870.0438130.013*
C80.15738 (8)0.30750 (19)0.04046 (5)0.0125 (3)
C90.03494 (8)0.21130 (18)0.07407 (5)0.0117 (3)
C100.04937 (8)0.28875 (19)0.07810 (6)0.0140 (3)
H10A0.0391570.3432280.1185540.021*
H10B0.0712490.3848040.0468900.021*
H10C0.0928840.1889230.0714870.021*
C110.06014 (8)0.03197 (19)0.07743 (5)0.0115 (3)
C120.01232 (8)0.12709 (19)0.09088 (6)0.0131 (3)
C130.09595 (10)0.2391 (2)0.13041 (7)0.0243 (3)
H13A0.0554510.3187140.1611580.036*
H13B0.1419640.1931580.1459870.036*
H13C0.1227760.3109880.0931000.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0216 (5)0.0117 (5)0.0346 (6)0.0002 (4)0.0152 (4)0.0019 (4)
O20.0205 (5)0.0130 (5)0.0274 (5)0.0022 (4)0.0160 (4)0.0009 (4)
O30.0169 (4)0.0130 (5)0.0209 (5)0.0000 (4)0.0102 (4)0.0027 (4)
F10.0219 (4)0.0623 (7)0.0188 (4)0.0054 (5)0.0030 (3)0.0114 (4)
N10.0142 (5)0.0089 (6)0.0180 (5)0.0015 (4)0.0089 (4)0.0003 (4)
N20.0137 (5)0.0124 (6)0.0144 (5)0.0024 (4)0.0085 (4)0.0021 (4)
C10.0168 (6)0.0183 (7)0.0182 (6)0.0034 (5)0.0075 (5)0.0031 (5)
C20.0171 (6)0.0280 (8)0.0236 (7)0.0090 (6)0.0066 (5)0.0096 (6)
C30.0142 (6)0.0389 (10)0.0151 (6)0.0009 (6)0.0022 (5)0.0107 (6)
C40.0223 (7)0.0319 (9)0.0141 (6)0.0031 (6)0.0043 (5)0.0021 (6)
C50.0186 (6)0.0212 (8)0.0168 (6)0.0025 (6)0.0054 (5)0.0003 (6)
C60.0115 (5)0.0154 (7)0.0128 (5)0.0010 (5)0.0052 (4)0.0023 (5)
C70.0119 (5)0.0094 (6)0.0131 (5)0.0002 (5)0.0050 (4)0.0001 (5)
C80.0115 (5)0.0146 (7)0.0110 (5)0.0014 (5)0.0033 (4)0.0014 (5)
C90.0111 (5)0.0141 (7)0.0103 (5)0.0004 (5)0.0041 (4)0.0012 (5)
C100.0125 (6)0.0130 (7)0.0176 (6)0.0016 (5)0.0063 (5)0.0003 (5)
C110.0107 (5)0.0133 (7)0.0110 (5)0.0001 (5)0.0043 (4)0.0013 (5)
C120.0115 (5)0.0139 (7)0.0139 (5)0.0003 (5)0.0041 (4)0.0005 (5)
C130.0252 (7)0.0190 (8)0.0362 (8)0.0047 (6)0.0202 (6)0.0006 (6)
Geometric parameters (Å, º) top
O1—C121.2140 (17)C4—C51.3943 (18)
O2—C121.3422 (15)C4—H40.9500
O2—C131.4441 (17)C5—C61.3943 (19)
O3—C81.2403 (16)C5—H50.9500
F1—C31.3630 (15)C6—C71.5265 (16)
N1—C81.3809 (16)C7—C111.5158 (17)
N1—C91.3890 (17)C7—H71.0000
N1—H1A0.891 (18)C9—C111.3473 (19)
N2—C81.3395 (18)C9—C101.4970 (17)
N2—C71.4709 (17)C10—H10A0.9800
N2—H2A0.875 (17)C10—H10B0.9800
C1—C61.3845 (19)C10—H10C0.9800
C1—C21.3975 (19)C11—C121.4676 (18)
C1—H10.9500C13—H13A0.9800
C2—C31.370 (2)C13—H13B0.9800
C2—H20.9500C13—H13C0.9800
C3—C41.373 (2)
C12—O2—C13115.48 (11)N2—C7—H7108.0
C8—N1—C9123.55 (12)C11—C7—H7108.0
C8—N1—H1A117.9 (10)C6—C7—H7108.0
C9—N1—H1A117.0 (10)O3—C8—N2124.02 (11)
C8—N2—C7123.53 (11)O3—C8—N1120.31 (12)
C8—N2—H2A116.7 (11)N2—C8—N1115.60 (11)
C7—N2—H2A117.2 (11)C11—C9—N1118.64 (11)
C6—C1—C2120.71 (13)C11—C9—C10127.93 (12)
C6—C1—H1119.6N1—C9—C10113.41 (11)
C2—C1—H1119.6C9—C10—H10A109.5
C3—C2—C1118.00 (14)C9—C10—H10B109.5
C3—C2—H2121.0H10A—C10—H10B109.5
C1—C2—H2121.0C9—C10—H10C109.5
F1—C3—C2118.34 (14)H10A—C10—H10C109.5
F1—C3—C4118.16 (14)H10B—C10—H10C109.5
C2—C3—C4123.50 (13)C9—C11—C12126.21 (11)
C3—C4—C5117.68 (13)C9—C11—C7120.39 (11)
C3—C4—H4121.2C12—C11—C7113.38 (11)
C5—C4—H4121.2O1—C12—O2122.04 (12)
C6—C5—C4120.87 (13)O1—C12—C11122.90 (11)
C6—C5—H5119.6O2—C12—C11114.99 (11)
C4—C5—H5119.6O2—C13—H13A109.5
C1—C6—C5119.20 (12)O2—C13—H13B109.5
C1—C6—C7120.13 (11)H13A—C13—H13B109.5
C5—C6—C7120.61 (12)O2—C13—H13C109.5
N2—C7—C11109.21 (10)H13A—C13—H13C109.5
N2—C7—C6110.93 (10)H13B—C13—H13C109.5
C11—C7—C6112.58 (10)
C6—C1—C2—C30.6 (2)C9—N1—C8—O3168.46 (11)
C1—C2—C3—F1179.16 (12)C9—N1—C8—N28.77 (17)
C1—C2—C3—C41.0 (2)C8—N1—C9—C1119.04 (18)
F1—C3—C4—C5179.00 (13)C8—N1—C9—C10159.33 (11)
C2—C3—C4—C51.1 (2)N1—C9—C11—C12176.58 (11)
C3—C4—C5—C60.3 (2)C10—C9—C11—C125.3 (2)
C2—C1—C6—C52.0 (2)N1—C9—C11—C71.35 (17)
C2—C1—C6—C7175.37 (12)C10—C9—C11—C7176.76 (11)
C4—C5—C6—C11.8 (2)N2—C7—C11—C921.92 (15)
C4—C5—C6—C7175.52 (12)C6—C7—C11—C9101.77 (13)
C8—N2—C7—C1133.69 (16)N2—C7—C11—C12159.91 (10)
C8—N2—C7—C690.96 (14)C6—C7—C11—C1276.41 (13)
C1—C6—C7—N2100.88 (14)C13—O2—C12—O13.22 (18)
C5—C6—C7—N276.42 (15)C13—O2—C12—C11179.83 (11)
C1—C6—C7—C11136.40 (13)C9—C11—C12—O1164.90 (13)
C5—C6—C7—C1146.31 (16)C7—C11—C12—O117.05 (17)
C7—N2—C8—O3163.16 (11)C9—C11—C12—O218.17 (18)
C7—N2—C8—N119.72 (17)C7—C11—C12—O2159.88 (10)
Methyl 4-(4-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate carbon tetrachloride 0.25-solvate (S1) top
Crystal data top
4C13H13FN2O3·CCl4F(000) = 1252
Mr = 1210.82Dx = 1.508 Mg m3
Monoclinic, P2/nMo Kα radiation, λ = 0.71073 Å
a = 16.2070 (7) ÅCell parameters from 4823 reflections
b = 9.1642 (4) Åθ = 2.5–28.6°
c = 17.9630 (7) ŵ = 0.31 mm1
β = 91.607 (2)°T = 100 K
V = 2666.89 (19) Å3Block, colourless
Z = 20.45 × 0.33 × 0.23 mm
Data collection top
Bruker APEXII CCD
diffractometer
3571 reflections with I > 2σ(I)
φ and ω scansRint = 0.051
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
θmax = 25.0°, θmin = 1.7°
Tmin = 0.586, Tmax = 0.746h = 1619
20706 measured reflectionsk = 1010
4601 independent reflectionsl = 1921
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.067H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.242 w = 1/[σ2(Fo2) + (0.1858P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
4601 reflectionsΔρmax = 0.56 e Å3
408 parametersΔρmin = 0.57 e Å3
22 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. SCXRD data of all single crystals of (I) were collected on a Bruker AXS SMART APEX CCD diffractometer using Mo Kα radiation (λ = 0.71073 Å) at 100 (2) K. Unit cell measurement, data collection, integration, scaling and absorption correction were performed using Bruker Apex II software and SAINT suite of programs were used for data reduction (Bruker, 2012). Scaling and absorption correction was performed using SADABAS software (Bruker, 2001). Crystal structures were solved using direct methods by SIR 2014 program (Burla et al., 2015) and refined using full matrix least squares method by SHELXL 2014 (Sheldrick, 2015) embedded in the WinGX program suite (Version 2014.1). Geometrical calculations were performed using PLATON (Spek, 2020) and PARST (Nardelli, 1995). Anisotropic refinement was performed for all non-hydrogen atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
F10.94589 (12)0.7597 (2)0.67373 (11)0.0330 (5)
F20.39469 (13)0.6525 (2)0.01540 (11)0.0379 (6)
C271.2416 (9)0.9780 (7)0.2478 (8)0.041 (2)0.5
Cl11.17515 (17)0.9088 (3)0.31424 (12)0.0496 (6)0.5
Cl21.3229 (6)1.0678 (8)0.2941 (4)0.101 (3)0.5
Cl31.2793 (2)0.8335 (3)0.19447 (15)0.0682 (8)0.5
Cl41.1841 (4)1.0981 (5)0.1923 (3)0.0398 (8)0.5
O10.50525 (14)0.6145 (2)0.65445 (12)0.0231 (6)
O20.57460 (14)0.4038 (2)0.64479 (11)0.0192 (5)
O30.67518 (13)0.6295 (2)0.34185 (11)0.0176 (5)
O40.75358 (15)1.2304 (2)0.09794 (13)0.0278 (6)
O50.73355 (13)0.9987 (2)0.06299 (11)0.0186 (5)
O60.56208 (14)0.9660 (2)0.36331 (11)0.0196 (5)
N10.60477 (16)0.7117 (3)0.44123 (13)0.0136 (6)
H1A0.589 (2)0.779 (4)0.4184 (19)0.017 (9)*
N20.67468 (16)0.4950 (3)0.44849 (13)0.0144 (6)
H2A0.707 (2)0.431 (4)0.4249 (17)0.012 (8)*
N30.58642 (17)1.1304 (3)0.27159 (14)0.0158 (6)
H3A0.556 (2)1.190 (4)0.2983 (18)0.024 (9)*
N40.63691 (15)0.8970 (2)0.26442 (13)0.0130 (6)
H4A0.640 (2)0.813 (2)0.2853 (16)0.016*
C10.7662 (2)0.5328 (3)0.64108 (17)0.0219 (7)
H10.7331660.4656090.6673690.026*
C20.8326 (2)0.5994 (4)0.67717 (17)0.0235 (8)
H20.8453170.5791320.7280800.028*
C30.87968 (19)0.6950 (3)0.63805 (18)0.0218 (8)
C40.8638 (2)0.7285 (3)0.56485 (17)0.0193 (7)
H40.8973540.7956000.5390950.023*
C50.79695 (19)0.6610 (3)0.52966 (16)0.0161 (7)
H50.7848250.6824810.4787820.019*
C60.74721 (18)0.5632 (3)0.56640 (15)0.0139 (7)
C70.67088 (18)0.4953 (3)0.52939 (16)0.0142 (7)
H70.6666520.3919160.5466850.017*
C80.65441 (19)0.6121 (3)0.40688 (16)0.0142 (7)
C90.56612 (18)0.6867 (3)0.50751 (15)0.0134 (7)
C100.4952 (2)0.7857 (3)0.52126 (17)0.0192 (7)
H10A0.4781420.8339380.4746290.029*
H10B0.5118750.8595320.5581930.029*
H10C0.4489920.7288430.5400070.029*
C110.59344 (18)0.5765 (3)0.55241 (15)0.0129 (6)
C120.55275 (19)0.5389 (3)0.62081 (15)0.0150 (7)
C130.5341 (2)0.3521 (3)0.70969 (17)0.0231 (7)
H13A0.5445310.2473530.7158020.035*
H13B0.4745610.3690200.7039320.035*
H13C0.5555420.4044600.7536880.035*
C140.5803 (2)0.6954 (3)0.12916 (15)0.0172 (7)
H140.6228520.6370810.1512590.021*
C150.5164 (2)0.6292 (3)0.08882 (17)0.0255 (8)
H150.5142180.5260810.0834600.031*
C160.4565 (2)0.7160 (3)0.05699 (17)0.0224 (8)
C170.4567 (2)0.8652 (4)0.06315 (18)0.0252 (8)
H170.4143510.9223650.0400800.030*
C180.52112 (19)0.9305 (3)0.10436 (17)0.0188 (7)
H180.5224431.0336030.1095700.023*
C190.58281 (18)0.8473 (3)0.13762 (15)0.0131 (6)
C200.65285 (19)0.9133 (3)0.18480 (15)0.0135 (6)
H200.7044060.8581230.1741270.016*
C210.59323 (19)0.9927 (3)0.30282 (15)0.0140 (7)
C220.63275 (18)1.1757 (3)0.21263 (15)0.0141 (7)
C230.6360 (2)1.3381 (3)0.20318 (18)0.0214 (7)
H23A0.6839401.3770530.2310400.032*
H23B0.5854551.3816900.2220620.032*
H23C0.6406211.3617740.1502570.032*
C240.66910 (18)1.0736 (3)0.16991 (15)0.0132 (6)
C250.72154 (18)1.1124 (3)0.10920 (16)0.0155 (7)
C260.7867 (2)1.0271 (4)0.00221 (17)0.0240 (8)
H26A0.7910010.9391680.0285150.036*
H26B0.8416681.0543260.0217300.036*
H26C0.7639021.1070840.0281280.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0209 (11)0.0409 (12)0.0364 (11)0.0103 (9)0.0128 (9)0.0012 (9)
F20.0371 (13)0.0349 (12)0.0408 (12)0.0214 (10)0.0149 (10)0.0064 (9)
C270.050 (6)0.040 (3)0.033 (3)0.002 (7)0.004 (4)0.002 (8)
Cl10.0594 (17)0.0571 (16)0.0326 (11)0.0251 (12)0.0036 (11)0.0006 (10)
Cl20.090 (5)0.101 (5)0.110 (5)0.048 (4)0.022 (4)0.028 (3)
Cl30.098 (3)0.0592 (17)0.0481 (14)0.0329 (17)0.0050 (15)0.0001 (13)
Cl40.0452 (19)0.0354 (14)0.0382 (13)0.0088 (12)0.0120 (12)0.0167 (12)
O10.0282 (14)0.0178 (12)0.0235 (12)0.0040 (10)0.0035 (10)0.0002 (9)
O20.0220 (13)0.0145 (11)0.0211 (11)0.0010 (9)0.0012 (9)0.0068 (8)
O30.0251 (13)0.0126 (11)0.0152 (11)0.0043 (9)0.0020 (9)0.0002 (8)
O40.0321 (14)0.0115 (11)0.0402 (14)0.0077 (10)0.0095 (11)0.0025 (10)
O50.0226 (13)0.0140 (11)0.0193 (11)0.0048 (9)0.0024 (9)0.0006 (8)
O60.0317 (14)0.0126 (10)0.0146 (10)0.0065 (9)0.0018 (9)0.0018 (8)
N10.0201 (15)0.0073 (12)0.0136 (12)0.0047 (10)0.0004 (10)0.0033 (10)
N20.0209 (15)0.0075 (12)0.0148 (12)0.0039 (11)0.0011 (11)0.0012 (9)
N30.0195 (15)0.0086 (12)0.0190 (13)0.0036 (11)0.0022 (11)0.0001 (10)
N40.0165 (14)0.0061 (12)0.0162 (12)0.0007 (10)0.0011 (10)0.0035 (9)
C10.0213 (18)0.0234 (17)0.0208 (15)0.0008 (13)0.0012 (13)0.0066 (13)
C20.0212 (18)0.0301 (18)0.0190 (15)0.0014 (14)0.0050 (13)0.0055 (13)
C30.0144 (17)0.0206 (17)0.0300 (17)0.0003 (13)0.0085 (14)0.0019 (13)
C40.0170 (17)0.0139 (15)0.0270 (16)0.0008 (12)0.0039 (13)0.0029 (12)
C50.0186 (17)0.0129 (15)0.0168 (15)0.0036 (12)0.0011 (12)0.0033 (11)
C60.0140 (16)0.0104 (14)0.0172 (14)0.0075 (12)0.0019 (12)0.0009 (11)
C70.0165 (17)0.0084 (14)0.0175 (14)0.0014 (11)0.0015 (12)0.0018 (11)
C80.0179 (16)0.0075 (14)0.0167 (15)0.0007 (11)0.0051 (12)0.0018 (11)
C90.0153 (16)0.0101 (14)0.0148 (14)0.0038 (12)0.0021 (12)0.0028 (11)
C100.0237 (18)0.0148 (15)0.0193 (15)0.0064 (13)0.0007 (13)0.0013 (12)
C110.0170 (16)0.0054 (13)0.0161 (14)0.0014 (11)0.0033 (12)0.0003 (11)
C120.0160 (16)0.0114 (14)0.0173 (14)0.0020 (12)0.0045 (12)0.0001 (12)
C130.0263 (19)0.0213 (17)0.0215 (16)0.0041 (14)0.0004 (14)0.0084 (13)
C140.0239 (18)0.0119 (15)0.0159 (14)0.0021 (12)0.0004 (13)0.0016 (11)
C150.041 (2)0.0121 (16)0.0228 (16)0.0098 (14)0.0019 (15)0.0021 (12)
C160.0210 (18)0.0236 (18)0.0222 (16)0.0118 (14)0.0033 (14)0.0047 (13)
C170.0173 (18)0.0243 (18)0.0334 (18)0.0017 (14)0.0103 (14)0.0002 (14)
C180.0170 (17)0.0110 (15)0.0283 (16)0.0006 (12)0.0034 (13)0.0033 (12)
C190.0164 (16)0.0094 (14)0.0136 (14)0.0038 (12)0.0030 (11)0.0000 (11)
C200.0146 (16)0.0085 (14)0.0171 (14)0.0005 (11)0.0019 (12)0.0017 (11)
C210.0181 (16)0.0086 (14)0.0147 (14)0.0001 (12)0.0070 (12)0.0007 (11)
C220.0133 (16)0.0094 (14)0.0191 (15)0.0001 (11)0.0070 (12)0.0025 (11)
C230.0253 (19)0.0071 (15)0.0315 (17)0.0006 (12)0.0054 (14)0.0021 (12)
C240.0129 (15)0.0080 (14)0.0184 (14)0.0030 (11)0.0056 (12)0.0022 (11)
C250.0127 (16)0.0103 (15)0.0233 (16)0.0027 (12)0.0040 (12)0.0039 (12)
C260.0252 (19)0.0261 (18)0.0210 (16)0.0034 (14)0.0015 (13)0.0033 (13)
Geometric parameters (Å, º) top
F1—C31.369 (3)C5—H50.9500
F2—C161.364 (3)C6—C71.521 (4)
C27—Cl41.738 (11)C7—C111.526 (4)
C27—Cl21.744 (12)C7—H71.0000
C27—Cl11.749 (12)C9—C111.359 (4)
C27—Cl31.754 (10)C9—C101.490 (4)
O1—C121.209 (4)C10—H10A0.9800
O2—C121.355 (3)C10—H10B0.9800
O2—C131.435 (4)C10—H10C0.9800
O3—C81.235 (4)C11—C121.452 (4)
O4—C251.219 (4)C13—H13A0.9800
O5—C251.350 (4)C13—H13B0.9800
O5—C261.434 (4)C13—H13C0.9800
O6—C211.235 (4)C14—C151.387 (4)
N1—C81.374 (4)C14—C191.401 (4)
N1—C91.380 (4)C14—H140.9500
N1—H1A0.78 (3)C15—C161.367 (5)
N2—C81.343 (4)C15—H150.9500
N2—C71.456 (4)C16—C171.372 (5)
N2—H2A0.90 (4)C17—C181.397 (4)
N3—C221.379 (4)C17—H170.9500
N3—C211.385 (4)C18—C191.380 (4)
N3—H3A0.88 (4)C18—H180.9500
N4—C211.332 (4)C19—C201.523 (4)
N4—C201.468 (4)C20—C241.517 (4)
N4—H4A0.856 (18)C20—H201.0000
C1—C21.383 (4)C22—C241.355 (4)
C1—C61.396 (4)C22—C231.499 (4)
C1—H10.9500C23—H23A0.9800
C2—C31.369 (5)C23—H23B0.9800
C2—H20.9500C23—H23C0.9800
C3—C41.368 (4)C24—C251.446 (4)
C4—C51.384 (4)C26—H26A0.9800
C4—H40.9500C26—H26B0.9800
C5—C61.385 (4)C26—H26C0.9800
Cl4—C27—Cl2111.1 (4)C12—C11—C7120.7 (2)
Cl4—C27—Cl1106.9 (7)O1—C12—O2121.9 (3)
Cl2—C27—Cl1108.5 (8)O1—C12—C11126.7 (3)
Cl4—C27—Cl3110.7 (8)O2—C12—C11111.4 (3)
Cl2—C27—Cl3110.3 (8)O2—C13—H13A109.5
Cl1—C27—Cl3109.2 (4)O2—C13—H13B109.5
C12—O2—C13116.0 (2)H13A—C13—H13B109.5
C25—O5—C26115.4 (2)O2—C13—H13C109.5
C8—N1—C9124.3 (3)H13A—C13—H13C109.5
C8—N1—H1A118 (3)H13B—C13—H13C109.5
C9—N1—H1A116 (3)C15—C14—C19120.7 (3)
C8—N2—C7122.5 (2)C15—C14—H14119.7
C8—N2—H2A113.2 (19)C19—C14—H14119.7
C7—N2—H2A120.9 (19)C16—C15—C14118.3 (3)
C22—N3—C21123.1 (3)C16—C15—H15120.8
C22—N3—H3A123 (2)C14—C15—H15120.8
C21—N3—H3A113 (2)F2—C16—C15118.9 (3)
C21—N4—C20123.2 (2)F2—C16—C17118.0 (3)
C21—N4—H4A113 (2)C15—C16—C17123.1 (3)
C20—N4—H4A121 (2)C16—C17—C18118.0 (3)
C2—C1—C6120.7 (3)C16—C17—H17121.0
C2—C1—H1119.7C18—C17—H17121.0
C6—C1—H1119.7C19—C18—C17120.9 (3)
C3—C2—C1118.7 (3)C19—C18—H18119.5
C3—C2—H2120.7C17—C18—H18119.5
C1—C2—H2120.7C18—C19—C14118.9 (3)
C4—C3—C2123.0 (3)C18—C19—C20122.8 (2)
C4—C3—F1118.5 (3)C14—C19—C20118.3 (3)
C2—C3—F1118.5 (3)N4—C20—C24107.9 (2)
C3—C4—C5117.6 (3)N4—C20—C19110.7 (2)
C3—C4—H4121.2C24—C20—C19114.6 (2)
C5—C4—H4121.2N4—C20—H20107.8
C4—C5—C6122.0 (3)C24—C20—H20107.8
C4—C5—H5119.0C19—C20—H20107.8
C6—C5—H5119.0O6—C21—N4124.2 (3)
C5—C6—C1118.1 (3)O6—C21—N3120.4 (3)
C5—C6—C7122.2 (2)N4—C21—N3115.3 (3)
C1—C6—C7119.5 (3)C24—C22—N3118.8 (3)
N2—C7—C6112.3 (2)C24—C22—C23127.2 (3)
N2—C7—C11109.2 (2)N3—C22—C23114.0 (3)
C6—C7—C11110.3 (2)C22—C23—H23A109.5
N2—C7—H7108.3C22—C23—H23B109.5
C6—C7—H7108.3H23A—C23—H23B109.5
C11—C7—H7108.3C22—C23—H23C109.5
O3—C8—N2124.1 (3)H23A—C23—H23C109.5
O3—C8—N1121.2 (3)H23B—C23—H23C109.5
N2—C8—N1114.7 (3)C22—C24—C25122.1 (3)
C11—C9—N1119.1 (3)C22—C24—C20119.2 (3)
C11—C9—C10126.5 (3)C25—C24—C20118.7 (3)
N1—C9—C10114.4 (2)O4—C25—O5120.9 (3)
C9—C10—H10A109.5O4—C25—C24127.3 (3)
C9—C10—H10B109.5O5—C25—C24111.8 (2)
H10A—C10—H10B109.5O5—C26—H26A109.5
C9—C10—H10C109.5O5—C26—H26B109.5
H10A—C10—H10C109.5H26A—C26—H26B109.5
H10B—C10—H10C109.5O5—C26—H26C109.5
C9—C11—C12122.0 (3)H26A—C26—H26C109.5
C9—C11—C7117.3 (3)H26B—C26—H26C109.5
C6—C1—C2—C30.4 (5)C19—C14—C15—C160.7 (5)
C1—C2—C3—C40.4 (5)C14—C15—C16—F2178.1 (3)
C1—C2—C3—F1179.3 (3)C14—C15—C16—C170.1 (5)
C2—C3—C4—C50.2 (5)F2—C16—C17—C18178.6 (3)
F1—C3—C4—C5179.5 (3)C15—C16—C17—C180.4 (5)
C3—C4—C5—C60.1 (4)C16—C17—C18—C190.2 (5)
C4—C5—C6—C10.2 (4)C17—C18—C19—C140.3 (5)
C4—C5—C6—C7176.4 (3)C17—C18—C19—C20178.3 (3)
C2—C1—C6—C50.3 (5)C15—C14—C19—C180.8 (5)
C2—C1—C6—C7176.4 (3)C15—C14—C19—C20177.8 (3)
C8—N2—C7—C682.3 (3)C21—N4—C20—C2439.2 (4)
C8—N2—C7—C1140.4 (4)C21—N4—C20—C1986.9 (3)
C5—C6—C7—N223.3 (4)C18—C19—C20—N4100.4 (3)
C1—C6—C7—N2160.1 (3)C14—C19—C20—N478.2 (3)
C5—C6—C7—C1198.9 (3)C18—C19—C20—C2421.8 (4)
C1—C6—C7—C1177.7 (3)C14—C19—C20—C24159.5 (3)
C7—N2—C8—O3161.6 (3)C20—N4—C21—O6161.6 (3)
C7—N2—C8—N121.0 (4)C20—N4—C21—N320.5 (4)
C9—N1—C8—O3166.8 (3)C22—N3—C21—O6166.7 (3)
C9—N1—C8—N210.7 (4)C22—N3—C21—N411.2 (4)
C8—N1—C9—C1118.0 (4)C21—N3—C22—C2418.9 (4)
C8—N1—C9—C10160.6 (3)C21—N3—C22—C23161.6 (3)
N1—C9—C11—C12176.5 (2)N3—C22—C24—C25177.2 (2)
C10—C9—C11—C122.0 (4)C23—C22—C24—C253.4 (4)
N1—C9—C11—C75.3 (4)N3—C22—C24—C204.3 (4)
C10—C9—C11—C7176.2 (3)C23—C22—C24—C20175.1 (3)
N2—C7—C11—C930.9 (3)N4—C20—C24—C2229.6 (3)
C6—C7—C11—C993.0 (3)C19—C20—C24—C2294.1 (3)
N2—C7—C11—C12150.8 (2)N4—C20—C24—C25151.8 (2)
C6—C7—C11—C1285.2 (3)C19—C20—C24—C2584.4 (3)
C13—O2—C12—O13.8 (4)C26—O5—C25—O41.0 (4)
C13—O2—C12—C11176.4 (2)C26—O5—C25—C24178.4 (2)
C9—C11—C12—O117.8 (4)C22—C24—C25—O416.5 (5)
C7—C11—C12—O1160.3 (3)C20—C24—C25—O4165.0 (3)
C9—C11—C12—O2162.4 (2)C22—C24—C25—O5164.0 (2)
C7—C11—C12—O219.4 (3)C20—C24—C25—O514.5 (3)
Methyl 4-(4-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate ethyl acetate hemisolvate (S2) top
Crystal data top
C13H13FN2O3·0.5C4H8O2Z = 2
Mr = 308.30F(000) = 324
Triclinic, P1Dx = 1.400 Mg m3
a = 7.3353 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.9091 (2) ÅCell parameters from 3724 reflections
c = 12.5006 (4) Åθ = 2.5–28.7°
α = 82.389 (2)°µ = 0.11 mm1
β = 79.380 (2)°T = 100 K
γ = 65.898 (2)°Rod, colourless
V = 731.44 (4) Å30.43 × 0.36 × 0.27 mm
Data collection top
Bruker APEXII CCD
diffractometer
2647 reflections with I > 2σ(I)
φ and ω scansRint = 0.034
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
θmax = 27.9°, θmin = 1.7°
Tmin = 0.706, Tmax = 0.746h = 99
14325 measured reflectionsk = 1111
3475 independent reflectionsl = 1616
Refinement top
Refinement on F2118 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.141 w = 1/[σ2(Fo2) + (0.061P)2 + 0.449P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3475 reflectionsΔρmax = 0.65 e Å3
238 parametersΔρmin = 0.34 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. SCXRD data of all single crystals of (I) were collected on a Bruker AXS SMART APEX CCD diffractometer using Mo Kα radiation (λ = 0.71073 Å) at 100 (2) K. Unit cell measurement, data collection, integration, scaling and absorption correction were performed using Bruker Apex II software and SAINT suite of programs were used for data reduction (Bruker, 2012). Scaling and absorption correction was performed using SADABAS software (Bruker, 2001). Crystal structures were solved using direct methods by SIR 2014 program (Burla et al., 2015) and refined using full matrix least squares method by SHELXL 2014 (Sheldrick, 2015) embedded in the WinGX program suite (Version 2014.1). Geometrical calculations were performed using PLATON (Spek, 2020) and PARST (Nardelli, 1995). Anisotropic refinement was performed for all non-hydrogen atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
F10.71212 (18)0.00939 (16)0.00525 (9)0.0395 (3)
O20.37279 (18)0.71184 (14)0.29141 (11)0.0255 (3)
O10.25071 (18)0.52266 (15)0.36519 (11)0.0257 (3)
O31.12712 (17)0.13882 (14)0.46283 (10)0.0221 (3)
N10.9368 (2)0.38577 (17)0.38433 (12)0.0200 (3)
H1A1.033 (4)0.413 (3)0.3854 (18)0.033 (6)*
N20.8049 (2)0.18943 (17)0.44248 (12)0.0199 (3)
H2A0.828 (3)0.088 (3)0.4704 (17)0.029 (5)*
C10.7875 (3)0.2155 (2)0.18991 (15)0.0253 (4)
H10.8656640.2765900.1943670.030*
C20.8095 (3)0.1448 (2)0.09401 (16)0.0283 (4)
H20.9015820.1563100.0324710.034*
C30.6944 (3)0.0573 (2)0.09024 (15)0.0272 (4)
C40.5615 (3)0.0362 (2)0.17711 (16)0.0299 (4)
H40.4856020.0264280.1719910.036*
C50.5402 (3)0.1084 (2)0.27287 (15)0.0245 (4)
H50.4479200.0958760.3339250.029*
C60.6525 (2)0.19882 (19)0.28032 (14)0.0192 (3)
C70.6294 (2)0.27781 (19)0.38548 (14)0.0177 (3)
H70.5079100.2714370.4341830.021*
C80.9645 (2)0.2302 (2)0.43101 (13)0.0187 (3)
C90.7506 (2)0.5048 (2)0.36381 (14)0.0196 (4)
C100.7483 (3)0.6749 (2)0.34535 (16)0.0258 (4)
H10A0.8043970.6921160.2695410.039*
H10B0.8297980.6881430.3944450.039*
H10C0.6091070.7558130.3599690.039*
C110.5968 (2)0.45782 (19)0.36440 (13)0.0178 (3)
C120.3918 (2)0.5651 (2)0.34235 (14)0.0197 (3)
C130.1708 (3)0.8203 (2)0.27048 (18)0.0324 (5)
H13A0.1266180.7698810.2207730.049*
H13B0.1712570.9261740.2371920.049*
H13C0.0781330.8382250.3393170.049*
O41.0043 (7)0.3710 (6)0.0909 (4)0.0739 (11)0.5
O51.0156 (9)0.5286 (9)0.0250 (7)0.0752 (13)0.5
C140.7037 (14)0.6047 (12)0.0313 (11)0.101 (2)0.5
H14A0.6727990.6708070.0997850.152*0.5
H14B0.6772120.6775880.0269650.152*0.5
H14C0.6186470.5413830.0124010.152*0.5
C150.9215 (17)0.4887 (15)0.0446 (11)0.0760 (15)0.5
C161.2183 (13)0.4257 (11)0.0214 (9)0.0803 (15)0.5
H16A1.2908890.4312530.0531410.096*0.5
H16B1.2333200.3103450.0411440.096*0.5
C171.3007 (11)0.4794 (8)0.0976 (7)0.0792 (17)0.5
H17A1.2721840.5969880.0822000.119*0.5
H17B1.4470500.4165540.0905280.119*0.5
H17C1.2391310.4612590.1720160.119*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0383 (7)0.0549 (8)0.0311 (6)0.0213 (6)0.0024 (5)0.0157 (6)
O20.0149 (6)0.0179 (6)0.0404 (7)0.0053 (5)0.0059 (5)0.0081 (5)
O10.0163 (6)0.0201 (6)0.0419 (8)0.0090 (5)0.0070 (5)0.0032 (5)
O30.0171 (6)0.0187 (6)0.0301 (7)0.0061 (5)0.0079 (5)0.0033 (5)
N10.0145 (7)0.0171 (7)0.0302 (8)0.0081 (6)0.0061 (6)0.0026 (6)
N20.0180 (7)0.0149 (7)0.0282 (8)0.0076 (5)0.0085 (6)0.0041 (6)
C10.0214 (9)0.0241 (9)0.0320 (10)0.0112 (7)0.0004 (7)0.0044 (7)
C20.0231 (9)0.0304 (9)0.0292 (10)0.0104 (8)0.0019 (7)0.0031 (8)
C30.0258 (9)0.0294 (9)0.0260 (9)0.0084 (8)0.0047 (7)0.0072 (7)
C40.0308 (10)0.0355 (10)0.0314 (10)0.0206 (8)0.0052 (8)0.0036 (8)
C50.0253 (9)0.0276 (9)0.0248 (9)0.0155 (7)0.0043 (7)0.0020 (7)
C60.0162 (8)0.0149 (7)0.0253 (8)0.0046 (6)0.0058 (6)0.0014 (6)
C70.0133 (7)0.0155 (7)0.0243 (8)0.0057 (6)0.0042 (6)0.0007 (6)
C80.0170 (8)0.0171 (7)0.0216 (8)0.0064 (6)0.0027 (6)0.0015 (6)
C90.0165 (8)0.0155 (7)0.0257 (9)0.0053 (6)0.0037 (7)0.0010 (6)
C100.0203 (9)0.0167 (8)0.0416 (11)0.0081 (7)0.0081 (8)0.0021 (7)
C110.0150 (8)0.0145 (7)0.0228 (8)0.0051 (6)0.0027 (6)0.0003 (6)
C120.0164 (8)0.0164 (8)0.0256 (8)0.0061 (6)0.0029 (7)0.0005 (6)
C130.0167 (9)0.0235 (9)0.0502 (12)0.0042 (7)0.0078 (8)0.0128 (8)
O40.072 (3)0.063 (2)0.095 (3)0.038 (2)0.005 (2)0.005 (2)
O50.068 (3)0.042 (2)0.126 (3)0.025 (3)0.036 (3)0.002 (2)
C140.086 (4)0.059 (4)0.155 (5)0.002 (3)0.067 (4)0.009 (4)
C150.070 (4)0.044 (2)0.124 (3)0.027 (3)0.032 (3)0.000 (2)
C160.071 (3)0.047 (3)0.128 (4)0.019 (3)0.038 (3)0.002 (3)
C170.074 (4)0.053 (3)0.109 (4)0.014 (3)0.044 (3)0.008 (3)
Geometric parameters (Å, º) top
F1—C31.365 (2)C7—H71.0000
O2—C121.340 (2)C9—C111.352 (2)
O2—C131.451 (2)C9—C101.496 (2)
O1—C121.216 (2)C10—H10A0.9800
O3—C81.2410 (19)C10—H10B0.9800
N1—C81.379 (2)C10—H10C0.9800
N1—C91.389 (2)C11—C121.470 (2)
N1—H1A0.84 (2)C13—H13A0.9800
N2—C81.340 (2)C13—H13B0.9800
N2—C71.465 (2)C13—H13C0.9800
N2—H2A0.88 (2)O4—C151.147 (14)
C1—C21.380 (3)O5—C151.364 (9)
C1—C61.394 (2)O5—C161.388 (10)
C1—H10.9500C14—C151.499 (12)
C2—C31.373 (3)C14—H14A0.9800
C2—H20.9500C14—H14B0.9800
C3—C41.367 (3)C14—H14C0.9800
C4—C51.387 (3)C16—C171.439 (12)
C4—H40.9500C16—H16A0.9900
C5—C61.387 (2)C16—H16B0.9900
C5—H50.9500C17—H17A0.9800
C6—C71.522 (2)C17—H17B0.9800
C7—C111.516 (2)C17—H17C0.9800
C12—O2—C13115.75 (13)H10A—C10—H10B109.5
C8—N1—C9123.70 (14)C9—C10—H10C109.5
C8—N1—H1A114.2 (15)H10A—C10—H10C109.5
C9—N1—H1A119.9 (15)H10B—C10—H10C109.5
C8—N2—C7124.17 (14)C9—C11—C12126.50 (15)
C8—N2—H2A114.0 (14)C9—C11—C7120.20 (14)
C7—N2—H2A119.3 (14)C12—C11—C7113.27 (14)
C2—C1—C6121.10 (17)O1—C12—O2122.16 (15)
C2—C1—H1119.4O1—C12—C11122.79 (15)
C6—C1—H1119.4O2—C12—C11115.01 (14)
C3—C2—C1118.00 (17)O2—C13—H13A109.5
C3—C2—H2121.0O2—C13—H13B109.5
C1—C2—H2121.0H13A—C13—H13B109.5
F1—C3—C4118.82 (17)O2—C13—H13C109.5
F1—C3—C2118.19 (17)H13A—C13—H13C109.5
C4—C3—C2122.99 (17)H13B—C13—H13C109.5
C3—C4—C5118.44 (17)C15—O5—C16113.2 (6)
C3—C4—H4120.8C15—C14—H14A109.5
C5—C4—H4120.8C15—C14—H14B109.5
C6—C5—C4120.63 (17)H14A—C14—H14B109.5
C6—C5—H5119.7C15—C14—H14C109.5
C4—C5—H5119.7H14A—C14—H14C109.5
C5—C6—C1118.83 (16)H14B—C14—H14C109.5
C5—C6—C7120.63 (15)O4—C15—O5120.3 (8)
C1—C6—C7120.54 (15)O4—C15—C14130.7 (8)
N2—C7—C11109.82 (13)O5—C15—C14108.3 (8)
N2—C7—C6111.24 (13)O5—C16—C17108.1 (7)
C11—C7—C6111.57 (13)O5—C16—H16A110.1
N2—C7—H7108.0C17—C16—H16A110.1
C11—C7—H7108.0O5—C16—H16B110.1
C6—C7—H7108.0C17—C16—H16B110.1
O3—C8—N2123.59 (15)H16A—C16—H16B108.4
O3—C8—N1120.46 (15)C16—C17—H17A109.5
N2—C8—N1115.90 (14)C16—C17—H17B109.5
C11—C9—N1118.86 (14)H17A—C17—H17B109.5
C11—C9—C10128.14 (15)C16—C17—H17C109.5
N1—C9—C10112.99 (14)H17A—C17—H17C109.5
C9—C10—H10A109.5H17B—C17—H17C109.5
C9—C10—H10B109.5
C6—C1—C2—C30.0 (3)C8—N1—C9—C1116.4 (3)
C1—C2—C3—F1178.43 (16)C8—N1—C9—C10162.49 (16)
C1—C2—C3—C40.7 (3)N1—C9—C11—C12178.65 (16)
F1—C3—C4—C5178.17 (16)C10—C9—C11—C122.6 (3)
C2—C3—C4—C50.9 (3)N1—C9—C11—C70.9 (2)
C3—C4—C5—C60.5 (3)C10—C9—C11—C7179.65 (17)
C4—C5—C6—C10.1 (3)N2—C7—C11—C921.5 (2)
C4—C5—C6—C7179.88 (16)C6—C7—C11—C9102.35 (18)
C2—C1—C6—C50.4 (3)N2—C7—C11—C12160.51 (14)
C2—C1—C6—C7179.86 (16)C6—C7—C11—C1275.67 (18)
C8—N2—C7—C1130.2 (2)C13—O2—C12—O13.2 (3)
C8—N2—C7—C693.77 (18)C13—O2—C12—C11179.11 (16)
C5—C6—C7—N2106.84 (17)C9—C11—C12—O1164.82 (18)
C1—C6—C7—N272.89 (19)C7—C11—C12—O117.3 (2)
C5—C6—C7—C11130.15 (16)C9—C11—C12—O217.5 (3)
C1—C6—C7—C1150.1 (2)C7—C11—C12—O2160.38 (14)
C7—N2—C8—O3166.08 (16)C16—O5—C15—O47.2 (12)
C7—N2—C8—N116.3 (2)C16—O5—C15—C14178.5 (10)
C9—N1—C8—O3168.65 (16)C15—O5—C16—C17180.0 (6)
C9—N1—C8—N29.1 (2)
 

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