Crystal structures of the anhydrous and two solvated forms of methyl 4-(4-fluoro­phen­yl)-6-methyl-2-oxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

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 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.

Computing details

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)

Crystal data

C13H13FN2O3	F(000) = 1104
Mr = 264.25	Dx = 1.382 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.0881 (15) Å	Cell parameters from 7891 reflections
b = 7.1958 (8) Å	θ = 2.7–29.9°
c = 23.177 (3) Å	µ = 0.11 mm^−1
β = 108.838 (4)°	T = 90 K
V = 2539.4 (5) Å^3	Plate, colourless
Z = 8	0.40 × 0.25 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer	2706 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.072
Absorption correction: multi-scan (SADABS; Bruker, 2001)	θmax = 30.1°, θmin = 2.7°
Tmin = 0.647, Tmax = 0.746	h = −22→22
24306 measured reflections	k = −9→10
3737 independent reflections	l = −32→32

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0511P)^2 + 1.7817P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3737 reflections	Δρmax = 0.39 e Å^−3
182 parameters	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.02856 (6)	0.28689 (14)	0.08155 (5)	0.0212 (2)
O2	−0.04829 (6)	0.08374 (13)	0.11713 (4)	0.0183 (2)
O3	0.19561 (6)	−0.43566 (13)	0.02354 (4)	0.0159 (2)
F1	0.42399 (6)	0.14688 (16)	0.28731 (4)	0.0366 (3)
N1	0.09065 (7)	−0.34590 (17)	0.06405 (5)	0.0128 (2)
H1A	0.0744 (10)	−0.464 (3)	0.0647 (7)	0.020 (4)*
N2	0.17380 (7)	−0.12694 (16)	0.03515 (5)	0.0126 (2)
H2A	0.2153 (11)	−0.100 (2)	0.0197 (8)	0.022 (4)*
C1	0.27321 (9)	0.2129 (2)	0.13482 (6)	0.0173 (3)
H1	0.263082	0.297493	0.101788	0.021*
C2	0.34316 (9)	0.2433 (2)	0.18837 (7)	0.0229 (3)
H2	0.381219	0.346839	0.192147	0.027*
C3	0.35521 (9)	0.1195 (2)	0.23523 (6)	0.0233 (3)
C4	0.30157 (9)	−0.0309 (2)	0.23263 (6)	0.0231 (3)
H4	0.311358	−0.112770	0.266334	0.028*
C5	0.23225 (9)	−0.0593 (2)	0.17878 (6)	0.0190 (3)
H5	0.193881	−0.161917	0.175722	0.023*
C6	0.21849 (8)	0.06081 (19)	0.12938 (5)	0.0129 (3)
C7	0.14667 (8)	0.02117 (18)	0.06901 (5)	0.0112 (2)
H7	0.136980	0.136887	0.043813	0.013*
C8	0.15738 (8)	−0.30750 (19)	0.04046 (5)	0.0125 (3)
C9	0.03494 (8)	−0.21130 (18)	0.07407 (5)	0.0117 (3)
C10	−0.04937 (8)	−0.28875 (19)	0.07810 (6)	0.0140 (3)
H10A	−0.039157	−0.343228	0.118554	0.021*
H10B	−0.071249	−0.384804	0.046890	0.021*
H10C	−0.092884	−0.188923	0.071487	0.021*
C11	0.06014 (8)	−0.03197 (19)	0.07743 (5)	0.0115 (3)
C12	0.01232 (8)	0.12709 (19)	0.09088 (6)	0.0131 (3)
C13	−0.09595 (10)	0.2391 (2)	0.13041 (7)	0.0243 (3)
H13A	−0.055451	0.318714	0.161158	0.036*
H13B	−0.141964	0.193158	0.145987	0.036*
H13C	−0.122776	0.310988	0.093100	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0216 (5)	0.0117 (5)	0.0346 (6)	0.0002 (4)	0.0152 (4)	0.0019 (4)
O2	0.0205 (5)	0.0130 (5)	0.0274 (5)	0.0022 (4)	0.0160 (4)	0.0009 (4)
O3	0.0169 (4)	0.0130 (5)	0.0209 (5)	0.0000 (4)	0.0102 (4)	−0.0027 (4)
F1	0.0219 (4)	0.0623 (7)	0.0188 (4)	−0.0054 (5)	−0.0030 (3)	−0.0114 (4)
N1	0.0142 (5)	0.0089 (6)	0.0180 (5)	−0.0015 (4)	0.0089 (4)	−0.0003 (4)
N2	0.0137 (5)	0.0124 (6)	0.0144 (5)	−0.0024 (4)	0.0085 (4)	−0.0021 (4)
C1	0.0168 (6)	0.0183 (7)	0.0182 (6)	−0.0034 (5)	0.0075 (5)	−0.0031 (5)
C2	0.0171 (6)	0.0280 (8)	0.0236 (7)	−0.0090 (6)	0.0066 (5)	−0.0096 (6)
C3	0.0142 (6)	0.0389 (10)	0.0151 (6)	−0.0009 (6)	0.0022 (5)	−0.0107 (6)
C4	0.0223 (7)	0.0319 (9)	0.0141 (6)	0.0031 (6)	0.0043 (5)	0.0021 (6)
C5	0.0186 (6)	0.0212 (8)	0.0168 (6)	−0.0025 (6)	0.0054 (5)	0.0003 (6)
C6	0.0115 (5)	0.0154 (7)	0.0128 (5)	0.0010 (5)	0.0052 (4)	−0.0023 (5)
C7	0.0119 (5)	0.0094 (6)	0.0131 (5)	−0.0002 (5)	0.0050 (4)	−0.0001 (5)
C8	0.0115 (5)	0.0146 (7)	0.0110 (5)	−0.0014 (5)	0.0033 (4)	−0.0014 (5)
C9	0.0111 (5)	0.0141 (7)	0.0103 (5)	0.0004 (5)	0.0041 (4)	0.0012 (5)
C10	0.0125 (6)	0.0130 (7)	0.0176 (6)	−0.0016 (5)	0.0063 (5)	0.0003 (5)
C11	0.0107 (5)	0.0133 (7)	0.0110 (5)	0.0001 (5)	0.0043 (4)	0.0013 (5)
C12	0.0115 (5)	0.0139 (7)	0.0139 (5)	−0.0003 (5)	0.0041 (4)	0.0005 (5)
C13	0.0252 (7)	0.0190 (8)	0.0362 (8)	0.0047 (6)	0.0202 (6)	−0.0006 (6)

Geometric parameters (Å, º)

O1—C12	1.2140 (17)	C4—C5	1.3943 (18)
O2—C12	1.3422 (15)	C4—H4	0.9500
O2—C13	1.4441 (17)	C5—C6	1.3943 (19)
O3—C8	1.2403 (16)	C5—H5	0.9500
F1—C3	1.3630 (15)	C6—C7	1.5265 (16)
N1—C8	1.3809 (16)	C7—C11	1.5158 (17)
N1—C9	1.3890 (17)	C7—H7	1.0000
N1—H1A	0.891 (18)	C9—C11	1.3473 (19)
N2—C8	1.3395 (18)	C9—C10	1.4970 (17)
N2—C7	1.4709 (17)	C10—H10A	0.9800
N2—H2A	0.875 (17)	C10—H10B	0.9800
C1—C6	1.3845 (19)	C10—H10C	0.9800
C1—C2	1.3975 (19)	C11—C12	1.4676 (18)
C1—H1	0.9500	C13—H13A	0.9800
C2—C3	1.370 (2)	C13—H13B	0.9800
C2—H2	0.9500	C13—H13C	0.9800
C3—C4	1.373 (2)
C12—O2—C13	115.48 (11)	N2—C7—H7	108.0
C8—N1—C9	123.55 (12)	C11—C7—H7	108.0
C8—N1—H1A	117.9 (10)	C6—C7—H7	108.0
C9—N1—H1A	117.0 (10)	O3—C8—N2	124.02 (11)
C8—N2—C7	123.53 (11)	O3—C8—N1	120.31 (12)
C8—N2—H2A	116.7 (11)	N2—C8—N1	115.60 (11)
C7—N2—H2A	117.2 (11)	C11—C9—N1	118.64 (11)
C6—C1—C2	120.71 (13)	C11—C9—C10	127.93 (12)
C6—C1—H1	119.6	N1—C9—C10	113.41 (11)
C2—C1—H1	119.6	C9—C10—H10A	109.5
C3—C2—C1	118.00 (14)	C9—C10—H10B	109.5
C3—C2—H2	121.0	H10A—C10—H10B	109.5
C1—C2—H2	121.0	C9—C10—H10C	109.5
F1—C3—C2	118.34 (14)	H10A—C10—H10C	109.5
F1—C3—C4	118.16 (14)	H10B—C10—H10C	109.5
C2—C3—C4	123.50 (13)	C9—C11—C12	126.21 (11)
C3—C4—C5	117.68 (13)	C9—C11—C7	120.39 (11)
C3—C4—H4	121.2	C12—C11—C7	113.38 (11)
C5—C4—H4	121.2	O1—C12—O2	122.04 (12)
C6—C5—C4	120.87 (13)	O1—C12—C11	122.90 (11)
C6—C5—H5	119.6	O2—C12—C11	114.99 (11)
C4—C5—H5	119.6	O2—C13—H13A	109.5
C1—C6—C5	119.20 (12)	O2—C13—H13B	109.5
C1—C6—C7	120.13 (11)	H13A—C13—H13B	109.5
C5—C6—C7	120.61 (12)	O2—C13—H13C	109.5
N2—C7—C11	109.21 (10)	H13A—C13—H13C	109.5
N2—C7—C6	110.93 (10)	H13B—C13—H13C	109.5
C11—C7—C6	112.58 (10)
C6—C1—C2—C3	−0.6 (2)	C9—N1—C8—O3	−168.46 (11)
C1—C2—C3—F1	179.16 (12)	C9—N1—C8—N2	8.77 (17)
C1—C2—C3—C4	−1.0 (2)	C8—N1—C9—C11	−19.04 (18)
F1—C3—C4—C5	−179.00 (13)	C8—N1—C9—C10	159.33 (11)
C2—C3—C4—C5	1.1 (2)	N1—C9—C11—C12	−176.58 (11)
C3—C4—C5—C6	0.3 (2)	C10—C9—C11—C12	5.3 (2)
C2—C1—C6—C5	2.0 (2)	N1—C9—C11—C7	1.35 (17)
C2—C1—C6—C7	−175.37 (12)	C10—C9—C11—C7	−176.76 (11)
C4—C5—C6—C1	−1.8 (2)	N2—C7—C11—C9	21.92 (15)
C4—C5—C6—C7	175.52 (12)	C6—C7—C11—C9	−101.77 (13)
C8—N2—C7—C11	−33.69 (16)	N2—C7—C11—C12	−159.91 (10)
C8—N2—C7—C6	90.96 (14)	C6—C7—C11—C12	76.41 (13)
C1—C6—C7—N2	100.88 (14)	C13—O2—C12—O1	3.22 (18)
C5—C6—C7—N2	−76.42 (15)	C13—O2—C12—C11	−179.83 (11)
C1—C6—C7—C11	−136.40 (13)	C9—C11—C12—O1	−164.90 (13)
C5—C6—C7—C11	46.31 (16)	C7—C11—C12—O1	17.05 (17)
C7—N2—C8—O3	−163.16 (11)	C9—C11—C12—O2	18.17 (18)
C7—N2—C8—N1	19.72 (17)	C7—C11—C12—O2	−159.88 (10)

Methyl 4-(4-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate carbon tetrachloride 0.25-solvate (S1)

Crystal data

4C13H13FN2O3·CCl4	F(000) = 1252
Mr = 1210.82	Dx = 1.508 Mg m^−3
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
a = 16.2070 (7) Å	Cell parameters from 4823 reflections
b = 9.1642 (4) Å	θ = 2.5–28.6°
c = 17.9630 (7) Å	µ = 0.31 mm^−1
β = 91.607 (2)°	T = 100 K
V = 2666.89 (19) Å^3	Block, colourless
Z = 2	0.45 × 0.33 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer	3571 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.051
Absorption correction: multi-scan (SADABS; Bruker, 2001)	θmax = 25.0°, θmin = 1.7°
Tmin = 0.586, Tmax = 0.746	h = −16→19
20706 measured reflections	k = −10→10
4601 independent reflections	l = −19→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.067	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.242	w = 1/[σ^2(Fo^2) + (0.1858P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
4601 reflections	Δρmax = 0.56 e Å^−3
408 parameters	Δρmin = −0.57 e Å^−3
22 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
F1	0.94589 (12)	0.7597 (2)	0.67373 (11)	0.0330 (5)
F2	0.39469 (13)	0.6525 (2)	0.01540 (11)	0.0379 (6)
C27	1.2416 (9)	0.9780 (7)	0.2478 (8)	0.041 (2)	0.5
Cl1	1.17515 (17)	0.9088 (3)	0.31424 (12)	0.0496 (6)	0.5
Cl2	1.3229 (6)	1.0678 (8)	0.2941 (4)	0.101 (3)	0.5
Cl3	1.2793 (2)	0.8335 (3)	0.19447 (15)	0.0682 (8)	0.5
Cl4	1.1841 (4)	1.0981 (5)	0.1923 (3)	0.0398 (8)	0.5
O1	0.50525 (14)	0.6145 (2)	0.65445 (12)	0.0231 (6)
O2	0.57460 (14)	0.4038 (2)	0.64479 (11)	0.0192 (5)
O3	0.67518 (13)	0.6295 (2)	0.34185 (11)	0.0176 (5)
O4	0.75358 (15)	1.2304 (2)	0.09794 (13)	0.0278 (6)
O5	0.73355 (13)	0.9987 (2)	0.06299 (11)	0.0186 (5)
O6	0.56208 (14)	0.9660 (2)	0.36331 (11)	0.0196 (5)
N1	0.60477 (16)	0.7117 (3)	0.44123 (13)	0.0136 (6)
H1A	0.589 (2)	0.779 (4)	0.4184 (19)	0.017 (9)*
N2	0.67468 (16)	0.4950 (3)	0.44849 (13)	0.0144 (6)
H2A	0.707 (2)	0.431 (4)	0.4249 (17)	0.012 (8)*
N3	0.58642 (17)	1.1304 (3)	0.27159 (14)	0.0158 (6)
H3A	0.556 (2)	1.190 (4)	0.2983 (18)	0.024 (9)*
N4	0.63691 (15)	0.8970 (2)	0.26442 (13)	0.0130 (6)
H4A	0.640 (2)	0.813 (2)	0.2853 (16)	0.016*
C1	0.7662 (2)	0.5328 (3)	0.64108 (17)	0.0219 (7)
H1	0.733166	0.465609	0.667369	0.026*
C2	0.8326 (2)	0.5994 (4)	0.67717 (17)	0.0235 (8)
H2	0.845317	0.579132	0.728080	0.028*
C3	0.87968 (19)	0.6950 (3)	0.63805 (18)	0.0218 (8)
C4	0.8638 (2)	0.7285 (3)	0.56485 (17)	0.0193 (7)
H4	0.897354	0.795600	0.539095	0.023*
C5	0.79695 (19)	0.6610 (3)	0.52966 (16)	0.0161 (7)
H5	0.784825	0.682481	0.478782	0.019*
C6	0.74721 (18)	0.5632 (3)	0.56640 (15)	0.0139 (7)
C7	0.67088 (18)	0.4953 (3)	0.52939 (16)	0.0142 (7)
H7	0.666652	0.391916	0.546685	0.017*
C8	0.65441 (19)	0.6121 (3)	0.40688 (16)	0.0142 (7)
C9	0.56612 (18)	0.6867 (3)	0.50751 (15)	0.0134 (7)
C10	0.4952 (2)	0.7857 (3)	0.52126 (17)	0.0192 (7)
H10A	0.478142	0.833938	0.474629	0.029*
H10B	0.511875	0.859532	0.558193	0.029*
H10C	0.448992	0.728843	0.540007	0.029*
C11	0.59344 (18)	0.5765 (3)	0.55241 (15)	0.0129 (6)
C12	0.55275 (19)	0.5389 (3)	0.62081 (15)	0.0150 (7)
C13	0.5341 (2)	0.3521 (3)	0.70969 (17)	0.0231 (7)
H13A	0.544531	0.247353	0.715802	0.035*
H13B	0.474561	0.369020	0.703932	0.035*
H13C	0.555542	0.404460	0.753688	0.035*
C14	0.5803 (2)	0.6954 (3)	0.12916 (15)	0.0172 (7)
H14	0.622852	0.637081	0.151259	0.021*
C15	0.5164 (2)	0.6292 (3)	0.08882 (17)	0.0255 (8)
H15	0.514218	0.526081	0.083460	0.031*
C16	0.4565 (2)	0.7160 (3)	0.05699 (17)	0.0224 (8)
C17	0.4567 (2)	0.8652 (4)	0.06315 (18)	0.0252 (8)
H17	0.414351	0.922365	0.040080	0.030*
C18	0.52112 (19)	0.9305 (3)	0.10436 (17)	0.0188 (7)
H18	0.522443	1.033603	0.109570	0.023*
C19	0.58281 (18)	0.8473 (3)	0.13762 (15)	0.0131 (6)
C20	0.65285 (19)	0.9133 (3)	0.18480 (15)	0.0135 (6)
H20	0.704406	0.858123	0.174127	0.016*
C21	0.59323 (19)	0.9927 (3)	0.30282 (15)	0.0140 (7)
C22	0.63275 (18)	1.1757 (3)	0.21263 (15)	0.0141 (7)
C23	0.6360 (2)	1.3381 (3)	0.20318 (18)	0.0214 (7)
H23A	0.683940	1.377053	0.231040	0.032*
H23B	0.585455	1.381690	0.222062	0.032*
H23C	0.640621	1.361774	0.150257	0.032*
C24	0.66910 (18)	1.0736 (3)	0.16991 (15)	0.0132 (6)
C25	0.72154 (18)	1.1124 (3)	0.10920 (16)	0.0155 (7)
C26	0.7867 (2)	1.0271 (4)	0.00221 (17)	0.0240 (8)
H26A	0.791001	0.939168	−0.028515	0.036*
H26B	0.841668	1.054326	0.021730	0.036*
H26C	0.763902	1.107084	−0.028128	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0209 (11)	0.0409 (12)	0.0364 (11)	−0.0103 (9)	−0.0128 (9)	0.0012 (9)
F2	0.0371 (13)	0.0349 (12)	0.0408 (12)	−0.0214 (10)	−0.0149 (10)	−0.0064 (9)
C27	0.050 (6)	0.040 (3)	0.033 (3)	0.002 (7)	0.004 (4)	−0.002 (8)
Cl1	0.0594 (17)	0.0571 (16)	0.0326 (11)	−0.0251 (12)	0.0036 (11)	0.0006 (10)
Cl2	0.090 (5)	0.101 (5)	0.110 (5)	−0.048 (4)	−0.022 (4)	0.028 (3)
Cl3	0.098 (3)	0.0592 (17)	0.0481 (14)	0.0329 (17)	0.0050 (15)	−0.0001 (13)
Cl4	0.0452 (19)	0.0354 (14)	0.0382 (13)	0.0088 (12)	−0.0120 (12)	−0.0167 (12)
O1	0.0282 (14)	0.0178 (12)	0.0235 (12)	0.0040 (10)	0.0035 (10)	0.0002 (9)
O2	0.0220 (13)	0.0145 (11)	0.0211 (11)	0.0010 (9)	0.0012 (9)	0.0068 (8)
O3	0.0251 (13)	0.0126 (11)	0.0152 (11)	0.0043 (9)	0.0020 (9)	0.0002 (8)
O4	0.0321 (14)	0.0115 (11)	0.0402 (14)	−0.0077 (10)	0.0095 (11)	0.0025 (10)
O5	0.0226 (13)	0.0140 (11)	0.0193 (11)	−0.0048 (9)	0.0024 (9)	0.0006 (8)
O6	0.0317 (14)	0.0126 (10)	0.0146 (10)	0.0065 (9)	0.0018 (9)	0.0018 (8)
N1	0.0201 (15)	0.0073 (12)	0.0136 (12)	0.0047 (10)	0.0004 (10)	0.0033 (10)
N2	0.0209 (15)	0.0075 (12)	0.0148 (12)	0.0039 (11)	−0.0011 (11)	−0.0012 (9)
N3	0.0195 (15)	0.0086 (12)	0.0190 (13)	0.0036 (11)	−0.0022 (11)	0.0001 (10)
N4	0.0165 (14)	0.0061 (12)	0.0162 (12)	0.0007 (10)	−0.0011 (10)	0.0035 (9)
C1	0.0213 (18)	0.0234 (17)	0.0208 (15)	0.0008 (13)	−0.0012 (13)	0.0066 (13)
C2	0.0212 (18)	0.0301 (18)	0.0190 (15)	−0.0014 (14)	−0.0050 (13)	0.0055 (13)
C3	0.0144 (17)	0.0206 (17)	0.0300 (17)	−0.0003 (13)	−0.0085 (14)	−0.0019 (13)
C4	0.0170 (17)	0.0139 (15)	0.0270 (16)	0.0008 (12)	0.0039 (13)	0.0029 (12)
C5	0.0186 (17)	0.0129 (15)	0.0168 (15)	0.0036 (12)	−0.0011 (12)	0.0033 (11)
C6	0.0140 (16)	0.0104 (14)	0.0172 (14)	0.0075 (12)	−0.0019 (12)	−0.0009 (11)
C7	0.0165 (17)	0.0084 (14)	0.0175 (14)	−0.0014 (11)	−0.0015 (12)	0.0018 (11)
C8	0.0179 (16)	0.0075 (14)	0.0167 (15)	−0.0007 (11)	−0.0051 (12)	−0.0018 (11)
C9	0.0153 (16)	0.0101 (14)	0.0148 (14)	−0.0038 (12)	−0.0021 (12)	−0.0028 (11)
C10	0.0237 (18)	0.0148 (15)	0.0193 (15)	0.0064 (13)	0.0007 (13)	0.0013 (12)
C11	0.0170 (16)	0.0054 (13)	0.0161 (14)	−0.0014 (11)	−0.0033 (12)	−0.0003 (11)
C12	0.0160 (16)	0.0114 (14)	0.0173 (14)	−0.0020 (12)	−0.0045 (12)	0.0001 (12)
C13	0.0263 (19)	0.0213 (17)	0.0215 (16)	−0.0041 (14)	0.0004 (14)	0.0084 (13)
C14	0.0239 (18)	0.0119 (15)	0.0159 (14)	−0.0021 (12)	0.0004 (13)	0.0016 (11)
C15	0.041 (2)	0.0121 (16)	0.0228 (16)	−0.0098 (14)	−0.0019 (15)	−0.0021 (12)
C16	0.0210 (18)	0.0236 (18)	0.0222 (16)	−0.0118 (14)	−0.0033 (14)	−0.0047 (13)
C17	0.0173 (18)	0.0243 (18)	0.0334 (18)	−0.0017 (14)	−0.0103 (14)	0.0002 (14)
C18	0.0170 (17)	0.0110 (15)	0.0283 (16)	−0.0006 (12)	−0.0034 (13)	−0.0033 (12)
C19	0.0164 (16)	0.0094 (14)	0.0136 (14)	−0.0038 (12)	0.0030 (11)	0.0000 (11)
C20	0.0146 (16)	0.0085 (14)	0.0171 (14)	0.0005 (11)	−0.0019 (12)	0.0017 (11)
C21	0.0181 (16)	0.0086 (14)	0.0147 (14)	−0.0001 (12)	−0.0070 (12)	0.0007 (11)
C22	0.0133 (16)	0.0094 (14)	0.0191 (15)	−0.0001 (11)	−0.0070 (12)	0.0025 (11)
C23	0.0253 (19)	0.0071 (15)	0.0315 (17)	0.0006 (12)	−0.0054 (14)	0.0021 (12)
C24	0.0129 (15)	0.0080 (14)	0.0184 (14)	−0.0030 (11)	−0.0056 (12)	0.0022 (11)
C25	0.0127 (16)	0.0103 (15)	0.0233 (16)	−0.0027 (12)	−0.0040 (12)	0.0039 (12)
C26	0.0252 (19)	0.0261 (18)	0.0210 (16)	−0.0034 (14)	0.0015 (13)	0.0033 (13)

Geometric parameters (Å, º)

F1—C3	1.369 (3)	C5—H5	0.9500
F2—C16	1.364 (3)	C6—C7	1.521 (4)
C27—Cl4	1.738 (11)	C7—C11	1.526 (4)
C27—Cl2	1.744 (12)	C7—H7	1.0000
C27—Cl1	1.749 (12)	C9—C11	1.359 (4)
C27—Cl3	1.754 (10)	C9—C10	1.490 (4)
O1—C12	1.209 (4)	C10—H10A	0.9800
O2—C12	1.355 (3)	C10—H10B	0.9800
O2—C13	1.435 (4)	C10—H10C	0.9800
O3—C8	1.235 (4)	C11—C12	1.452 (4)
O4—C25	1.219 (4)	C13—H13A	0.9800
O5—C25	1.350 (4)	C13—H13B	0.9800
O5—C26	1.434 (4)	C13—H13C	0.9800
O6—C21	1.235 (4)	C14—C15	1.387 (4)
N1—C8	1.374 (4)	C14—C19	1.401 (4)
N1—C9	1.380 (4)	C14—H14	0.9500
N1—H1A	0.78 (3)	C15—C16	1.367 (5)
N2—C8	1.343 (4)	C15—H15	0.9500
N2—C7	1.456 (4)	C16—C17	1.372 (5)
N2—H2A	0.90 (4)	C17—C18	1.397 (4)
N3—C22	1.379 (4)	C17—H17	0.9500
N3—C21	1.385 (4)	C18—C19	1.380 (4)
N3—H3A	0.88 (4)	C18—H18	0.9500
N4—C21	1.332 (4)	C19—C20	1.523 (4)
N4—C20	1.468 (4)	C20—C24	1.517 (4)
N4—H4A	0.856 (18)	C20—H20	1.0000
C1—C2	1.383 (4)	C22—C24	1.355 (4)
C1—C6	1.396 (4)	C22—C23	1.499 (4)
C1—H1	0.9500	C23—H23A	0.9800
C2—C3	1.369 (5)	C23—H23B	0.9800
C2—H2	0.9500	C23—H23C	0.9800
C3—C4	1.368 (4)	C24—C25	1.446 (4)
C4—C5	1.384 (4)	C26—H26A	0.9800
C4—H4	0.9500	C26—H26B	0.9800
C5—C6	1.385 (4)	C26—H26C	0.9800
Cl4—C27—Cl2	111.1 (4)	C12—C11—C7	120.7 (2)
Cl4—C27—Cl1	106.9 (7)	O1—C12—O2	121.9 (3)
Cl2—C27—Cl1	108.5 (8)	O1—C12—C11	126.7 (3)
Cl4—C27—Cl3	110.7 (8)	O2—C12—C11	111.4 (3)
Cl2—C27—Cl3	110.3 (8)	O2—C13—H13A	109.5
Cl1—C27—Cl3	109.2 (4)	O2—C13—H13B	109.5
C12—O2—C13	116.0 (2)	H13A—C13—H13B	109.5
C25—O5—C26	115.4 (2)	O2—C13—H13C	109.5
C8—N1—C9	124.3 (3)	H13A—C13—H13C	109.5
C8—N1—H1A	118 (3)	H13B—C13—H13C	109.5
C9—N1—H1A	116 (3)	C15—C14—C19	120.7 (3)
C8—N2—C7	122.5 (2)	C15—C14—H14	119.7
C8—N2—H2A	113.2 (19)	C19—C14—H14	119.7
C7—N2—H2A	120.9 (19)	C16—C15—C14	118.3 (3)
C22—N3—C21	123.1 (3)	C16—C15—H15	120.8
C22—N3—H3A	123 (2)	C14—C15—H15	120.8
C21—N3—H3A	113 (2)	F2—C16—C15	118.9 (3)
C21—N4—C20	123.2 (2)	F2—C16—C17	118.0 (3)
C21—N4—H4A	113 (2)	C15—C16—C17	123.1 (3)
C20—N4—H4A	121 (2)	C16—C17—C18	118.0 (3)
C2—C1—C6	120.7 (3)	C16—C17—H17	121.0
C2—C1—H1	119.7	C18—C17—H17	121.0
C6—C1—H1	119.7	C19—C18—C17	120.9 (3)
C3—C2—C1	118.7 (3)	C19—C18—H18	119.5
C3—C2—H2	120.7	C17—C18—H18	119.5
C1—C2—H2	120.7	C18—C19—C14	118.9 (3)
C4—C3—C2	123.0 (3)	C18—C19—C20	122.8 (2)
C4—C3—F1	118.5 (3)	C14—C19—C20	118.3 (3)
C2—C3—F1	118.5 (3)	N4—C20—C24	107.9 (2)
C3—C4—C5	117.6 (3)	N4—C20—C19	110.7 (2)
C3—C4—H4	121.2	C24—C20—C19	114.6 (2)
C5—C4—H4	121.2	N4—C20—H20	107.8
C4—C5—C6	122.0 (3)	C24—C20—H20	107.8
C4—C5—H5	119.0	C19—C20—H20	107.8
C6—C5—H5	119.0	O6—C21—N4	124.2 (3)
C5—C6—C1	118.1 (3)	O6—C21—N3	120.4 (3)
C5—C6—C7	122.2 (2)	N4—C21—N3	115.3 (3)
C1—C6—C7	119.5 (3)	C24—C22—N3	118.8 (3)
N2—C7—C6	112.3 (2)	C24—C22—C23	127.2 (3)
N2—C7—C11	109.2 (2)	N3—C22—C23	114.0 (3)
C6—C7—C11	110.3 (2)	C22—C23—H23A	109.5
N2—C7—H7	108.3	C22—C23—H23B	109.5
C6—C7—H7	108.3	H23A—C23—H23B	109.5
C11—C7—H7	108.3	C22—C23—H23C	109.5
O3—C8—N2	124.1 (3)	H23A—C23—H23C	109.5
O3—C8—N1	121.2 (3)	H23B—C23—H23C	109.5
N2—C8—N1	114.7 (3)	C22—C24—C25	122.1 (3)
C11—C9—N1	119.1 (3)	C22—C24—C20	119.2 (3)
C11—C9—C10	126.5 (3)	C25—C24—C20	118.7 (3)
N1—C9—C10	114.4 (2)	O4—C25—O5	120.9 (3)
C9—C10—H10A	109.5	O4—C25—C24	127.3 (3)
C9—C10—H10B	109.5	O5—C25—C24	111.8 (2)
H10A—C10—H10B	109.5	O5—C26—H26A	109.5
C9—C10—H10C	109.5	O5—C26—H26B	109.5
H10A—C10—H10C	109.5	H26A—C26—H26B	109.5
H10B—C10—H10C	109.5	O5—C26—H26C	109.5
C9—C11—C12	122.0 (3)	H26A—C26—H26C	109.5
C9—C11—C7	117.3 (3)	H26B—C26—H26C	109.5
C6—C1—C2—C3	−0.4 (5)	C19—C14—C15—C16	0.7 (5)
C1—C2—C3—C4	0.4 (5)	C14—C15—C16—F2	178.1 (3)
C1—C2—C3—F1	−179.3 (3)	C14—C15—C16—C17	−0.1 (5)
C2—C3—C4—C5	−0.2 (5)	F2—C16—C17—C18	−178.6 (3)
F1—C3—C4—C5	179.5 (3)	C15—C16—C17—C18	−0.4 (5)
C3—C4—C5—C6	0.1 (4)	C16—C17—C18—C19	0.2 (5)
C4—C5—C6—C1	−0.2 (4)	C17—C18—C19—C14	0.3 (5)
C4—C5—C6—C7	176.4 (3)	C17—C18—C19—C20	−178.3 (3)
C2—C1—C6—C5	0.3 (5)	C15—C14—C19—C18	−0.8 (5)
C2—C1—C6—C7	−176.4 (3)	C15—C14—C19—C20	177.8 (3)
C8—N2—C7—C6	−82.3 (3)	C21—N4—C20—C24	39.2 (4)
C8—N2—C7—C11	40.4 (4)	C21—N4—C20—C19	−86.9 (3)
C5—C6—C7—N2	23.3 (4)	C18—C19—C20—N4	100.4 (3)
C1—C6—C7—N2	−160.1 (3)	C14—C19—C20—N4	−78.2 (3)
C5—C6—C7—C11	−98.9 (3)	C18—C19—C20—C24	−21.8 (4)
C1—C6—C7—C11	77.7 (3)	C14—C19—C20—C24	159.5 (3)
C7—N2—C8—O3	161.6 (3)	C20—N4—C21—O6	161.6 (3)
C7—N2—C8—N1	−21.0 (4)	C20—N4—C21—N3	−20.5 (4)
C9—N1—C8—O3	166.8 (3)	C22—N3—C21—O6	166.7 (3)
C9—N1—C8—N2	−10.7 (4)	C22—N3—C21—N4	−11.2 (4)
C8—N1—C9—C11	18.0 (4)	C21—N3—C22—C24	18.9 (4)
C8—N1—C9—C10	−160.6 (3)	C21—N3—C22—C23	−161.6 (3)
N1—C9—C11—C12	−176.5 (2)	N3—C22—C24—C25	−177.2 (2)
C10—C9—C11—C12	2.0 (4)	C23—C22—C24—C25	3.4 (4)
N1—C9—C11—C7	5.3 (4)	N3—C22—C24—C20	4.3 (4)
C10—C9—C11—C7	−176.2 (3)	C23—C22—C24—C20	−175.1 (3)
N2—C7—C11—C9	−30.9 (3)	N4—C20—C24—C22	−29.6 (3)
C6—C7—C11—C9	93.0 (3)	C19—C20—C24—C22	94.1 (3)
N2—C7—C11—C12	150.8 (2)	N4—C20—C24—C25	151.8 (2)
C6—C7—C11—C12	−85.2 (3)	C19—C20—C24—C25	−84.4 (3)
C13—O2—C12—O1	3.8 (4)	C26—O5—C25—O4	1.0 (4)
C13—O2—C12—C11	−176.4 (2)	C26—O5—C25—C24	−178.4 (2)
C9—C11—C12—O1	−17.8 (4)	C22—C24—C25—O4	16.5 (5)
C7—C11—C12—O1	160.3 (3)	C20—C24—C25—O4	−165.0 (3)
C9—C11—C12—O2	162.4 (2)	C22—C24—C25—O5	−164.0 (2)
C7—C11—C12—O2	−19.4 (3)	C20—C24—C25—O5	14.5 (3)

Methyl 4-(4-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate ethyl acetate hemisolvate (S2)

Crystal data

C13H13FN2O3·0.5C4H8O2	Z = 2
Mr = 308.30	F(000) = 324
Triclinic, P1	Dx = 1.400 Mg m^−3
a = 7.3353 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9091 (2) Å	Cell parameters from 3724 reflections
c = 12.5006 (4) Å	θ = 2.5–28.7°
α = 82.389 (2)°	µ = 0.11 mm^−1
β = 79.380 (2)°	T = 100 K
γ = 65.898 (2)°	Rod, colourless
V = 731.44 (4) Å^3	0.43 × 0.36 × 0.27 mm

Data collection

Bruker APEXII CCD diffractometer	2647 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.034
Absorption correction: multi-scan (SADABS; Bruker, 2001)	θmax = 27.9°, θmin = 1.7°
Tmin = 0.706, Tmax = 0.746	h = −9→9
14325 measured reflections	k = −11→11
3475 independent reflections	l = −16→16

Refinement

Refinement on F^2	118 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.141	w = 1/[σ^2(Fo^2) + (0.061P)^2 + 0.449P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3475 reflections	Δρmax = 0.65 e Å^−3
238 parameters	Δρmin = −0.34 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
F1	0.71212 (18)	−0.00939 (16)	−0.00525 (9)	0.0395 (3)
O2	0.37279 (18)	0.71184 (14)	0.29141 (11)	0.0255 (3)
O1	0.25071 (18)	0.52266 (15)	0.36519 (11)	0.0257 (3)
O3	1.12712 (17)	0.13882 (14)	0.46283 (10)	0.0221 (3)
N1	0.9368 (2)	0.38577 (17)	0.38433 (12)	0.0200 (3)
H1A	1.033 (4)	0.413 (3)	0.3854 (18)	0.033 (6)*
N2	0.8049 (2)	0.18943 (17)	0.44248 (12)	0.0199 (3)
H2A	0.828 (3)	0.088 (3)	0.4704 (17)	0.029 (5)*
C1	0.7875 (3)	0.2155 (2)	0.18991 (15)	0.0253 (4)
H1	0.865664	0.276590	0.194367	0.030*
C2	0.8095 (3)	0.1448 (2)	0.09401 (16)	0.0283 (4)
H2	0.901582	0.156310	0.032471	0.034*
C3	0.6944 (3)	0.0573 (2)	0.09024 (15)	0.0272 (4)
C4	0.5615 (3)	0.0362 (2)	0.17711 (16)	0.0299 (4)
H4	0.485602	−0.026428	0.171991	0.036*
C5	0.5402 (3)	0.1084 (2)	0.27287 (15)	0.0245 (4)
H5	0.447920	0.095876	0.333925	0.029*
C6	0.6525 (2)	0.19882 (19)	0.28032 (14)	0.0192 (3)
C7	0.6294 (2)	0.27781 (19)	0.38548 (14)	0.0177 (3)
H7	0.507910	0.271437	0.434183	0.021*
C8	0.9645 (2)	0.2302 (2)	0.43101 (13)	0.0187 (3)
C9	0.7506 (2)	0.5048 (2)	0.36381 (14)	0.0196 (4)
C10	0.7483 (3)	0.6749 (2)	0.34535 (16)	0.0258 (4)
H10A	0.804397	0.692116	0.269541	0.039*
H10B	0.829798	0.688143	0.394445	0.039*
H10C	0.609107	0.755813	0.359969	0.039*
C11	0.5968 (2)	0.45782 (19)	0.36440 (13)	0.0178 (3)
C12	0.3918 (2)	0.5651 (2)	0.34235 (14)	0.0197 (3)
C13	0.1708 (3)	0.8203 (2)	0.27048 (18)	0.0324 (5)
H13A	0.126618	0.769881	0.220773	0.049*
H13B	0.171257	0.926174	0.237192	0.049*
H13C	0.078133	0.838225	0.339317	0.049*
O4	1.0043 (7)	0.3710 (6)	−0.0909 (4)	0.0739 (11)	0.5
O5	1.0156 (9)	0.5286 (9)	0.0250 (7)	0.0752 (13)	0.5
C14	0.7037 (14)	0.6047 (12)	−0.0313 (11)	0.101 (2)	0.5
H14A	0.672799	0.670807	−0.099785	0.152*	0.5
H14B	0.677212	0.677588	0.026965	0.152*	0.5
H14C	0.618647	0.541383	−0.012401	0.152*	0.5
C15	0.9215 (17)	0.4887 (15)	−0.0446 (11)	0.0760 (15)	0.5
C16	1.2183 (13)	0.4257 (11)	0.0214 (9)	0.0803 (15)	0.5
H16A	1.290889	0.431253	−0.053141	0.096*	0.5
H16B	1.233320	0.310345	0.041144	0.096*	0.5
C17	1.3007 (11)	0.4794 (8)	0.0976 (7)	0.0792 (17)	0.5
H17A	1.272184	0.596988	0.082200	0.119*	0.5
H17B	1.447050	0.416554	0.090528	0.119*	0.5
H17C	1.239131	0.461259	0.172016	0.119*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0383 (7)	0.0549 (8)	0.0311 (6)	−0.0213 (6)	−0.0024 (5)	−0.0157 (6)
O2	0.0149 (6)	0.0179 (6)	0.0404 (7)	−0.0053 (5)	−0.0059 (5)	0.0081 (5)
O1	0.0163 (6)	0.0201 (6)	0.0419 (8)	−0.0090 (5)	−0.0070 (5)	0.0032 (5)
O3	0.0171 (6)	0.0187 (6)	0.0301 (7)	−0.0061 (5)	−0.0079 (5)	0.0033 (5)
N1	0.0145 (7)	0.0171 (7)	0.0302 (8)	−0.0081 (6)	−0.0061 (6)	0.0026 (6)
N2	0.0180 (7)	0.0149 (7)	0.0282 (8)	−0.0076 (5)	−0.0085 (6)	0.0041 (6)
C1	0.0214 (9)	0.0241 (9)	0.0320 (10)	−0.0112 (7)	−0.0004 (7)	−0.0044 (7)
C2	0.0231 (9)	0.0304 (9)	0.0292 (10)	−0.0104 (8)	0.0019 (7)	−0.0031 (8)
C3	0.0258 (9)	0.0294 (9)	0.0260 (9)	−0.0084 (8)	−0.0047 (7)	−0.0072 (7)
C4	0.0308 (10)	0.0355 (10)	0.0314 (10)	−0.0206 (8)	−0.0052 (8)	−0.0036 (8)
C5	0.0253 (9)	0.0276 (9)	0.0248 (9)	−0.0155 (7)	−0.0043 (7)	0.0020 (7)
C6	0.0162 (8)	0.0149 (7)	0.0253 (8)	−0.0046 (6)	−0.0058 (6)	0.0014 (6)
C7	0.0133 (7)	0.0155 (7)	0.0243 (8)	−0.0057 (6)	−0.0042 (6)	0.0007 (6)
C8	0.0170 (8)	0.0171 (7)	0.0216 (8)	−0.0064 (6)	−0.0027 (6)	−0.0015 (6)
C9	0.0165 (8)	0.0155 (7)	0.0257 (9)	−0.0053 (6)	−0.0037 (7)	0.0010 (6)
C10	0.0203 (9)	0.0167 (8)	0.0416 (11)	−0.0081 (7)	−0.0081 (8)	0.0021 (7)
C11	0.0150 (8)	0.0145 (7)	0.0228 (8)	−0.0051 (6)	−0.0027 (6)	0.0003 (6)
C12	0.0164 (8)	0.0164 (8)	0.0256 (8)	−0.0061 (6)	−0.0029 (7)	−0.0005 (6)
C13	0.0167 (9)	0.0235 (9)	0.0502 (12)	−0.0042 (7)	−0.0078 (8)	0.0128 (8)
O4	0.072 (3)	0.063 (2)	0.095 (3)	−0.038 (2)	−0.005 (2)	−0.005 (2)
O5	0.068 (3)	0.042 (2)	0.126 (3)	−0.025 (3)	−0.036 (3)	−0.002 (2)
C14	0.086 (4)	0.059 (4)	0.155 (5)	−0.002 (3)	−0.067 (4)	−0.009 (4)
C15	0.070 (4)	0.044 (2)	0.124 (3)	−0.027 (3)	−0.032 (3)	0.000 (2)
C16	0.071 (3)	0.047 (3)	0.128 (4)	−0.019 (3)	−0.038 (3)	−0.002 (3)
C17	0.074 (4)	0.053 (3)	0.109 (4)	−0.014 (3)	−0.044 (3)	0.008 (3)

Geometric parameters (Å, º)

F1—C3	1.365 (2)	C7—H7	1.0000
O2—C12	1.340 (2)	C9—C11	1.352 (2)
O2—C13	1.451 (2)	C9—C10	1.496 (2)
O1—C12	1.216 (2)	C10—H10A	0.9800
O3—C8	1.2410 (19)	C10—H10B	0.9800
N1—C8	1.379 (2)	C10—H10C	0.9800
N1—C9	1.389 (2)	C11—C12	1.470 (2)
N1—H1A	0.84 (2)	C13—H13A	0.9800
N2—C8	1.340 (2)	C13—H13B	0.9800
N2—C7	1.465 (2)	C13—H13C	0.9800
N2—H2A	0.88 (2)	O4—C15	1.147 (14)
C1—C2	1.380 (3)	O5—C15	1.364 (9)
C1—C6	1.394 (2)	O5—C16	1.388 (10)
C1—H1	0.9500	C14—C15	1.499 (12)
C2—C3	1.373 (3)	C14—H14A	0.9800
C2—H2	0.9500	C14—H14B	0.9800
C3—C4	1.367 (3)	C14—H14C	0.9800
C4—C5	1.387 (3)	C16—C17	1.439 (12)
C4—H4	0.9500	C16—H16A	0.9900
C5—C6	1.387 (2)	C16—H16B	0.9900
C5—H5	0.9500	C17—H17A	0.9800
C6—C7	1.522 (2)	C17—H17B	0.9800
C7—C11	1.516 (2)	C17—H17C	0.9800
C12—O2—C13	115.75 (13)	H10A—C10—H10B	109.5
C8—N1—C9	123.70 (14)	C9—C10—H10C	109.5
C8—N1—H1A	114.2 (15)	H10A—C10—H10C	109.5
C9—N1—H1A	119.9 (15)	H10B—C10—H10C	109.5
C8—N2—C7	124.17 (14)	C9—C11—C12	126.50 (15)
C8—N2—H2A	114.0 (14)	C9—C11—C7	120.20 (14)
C7—N2—H2A	119.3 (14)	C12—C11—C7	113.27 (14)
C2—C1—C6	121.10 (17)	O1—C12—O2	122.16 (15)
C2—C1—H1	119.4	O1—C12—C11	122.79 (15)
C6—C1—H1	119.4	O2—C12—C11	115.01 (14)
C3—C2—C1	118.00 (17)	O2—C13—H13A	109.5
C3—C2—H2	121.0	O2—C13—H13B	109.5
C1—C2—H2	121.0	H13A—C13—H13B	109.5
F1—C3—C4	118.82 (17)	O2—C13—H13C	109.5
F1—C3—C2	118.19 (17)	H13A—C13—H13C	109.5
C4—C3—C2	122.99 (17)	H13B—C13—H13C	109.5
C3—C4—C5	118.44 (17)	C15—O5—C16	113.2 (6)
C3—C4—H4	120.8	C15—C14—H14A	109.5
C5—C4—H4	120.8	C15—C14—H14B	109.5
C6—C5—C4	120.63 (17)	H14A—C14—H14B	109.5
C6—C5—H5	119.7	C15—C14—H14C	109.5
C4—C5—H5	119.7	H14A—C14—H14C	109.5
C5—C6—C1	118.83 (16)	H14B—C14—H14C	109.5
C5—C6—C7	120.63 (15)	O4—C15—O5	120.3 (8)
C1—C6—C7	120.54 (15)	O4—C15—C14	130.7 (8)
N2—C7—C11	109.82 (13)	O5—C15—C14	108.3 (8)
N2—C7—C6	111.24 (13)	O5—C16—C17	108.1 (7)
C11—C7—C6	111.57 (13)	O5—C16—H16A	110.1
N2—C7—H7	108.0	C17—C16—H16A	110.1
C11—C7—H7	108.0	O5—C16—H16B	110.1
C6—C7—H7	108.0	C17—C16—H16B	110.1
O3—C8—N2	123.59 (15)	H16A—C16—H16B	108.4
O3—C8—N1	120.46 (15)	C16—C17—H17A	109.5
N2—C8—N1	115.90 (14)	C16—C17—H17B	109.5
C11—C9—N1	118.86 (14)	H17A—C17—H17B	109.5
C11—C9—C10	128.14 (15)	C16—C17—H17C	109.5
N1—C9—C10	112.99 (14)	H17A—C17—H17C	109.5
C9—C10—H10A	109.5	H17B—C17—H17C	109.5
C9—C10—H10B	109.5
C6—C1—C2—C3	0.0 (3)	C8—N1—C9—C11	−16.4 (3)
C1—C2—C3—F1	178.43 (16)	C8—N1—C9—C10	162.49 (16)
C1—C2—C3—C4	−0.7 (3)	N1—C9—C11—C12	−178.65 (16)
F1—C3—C4—C5	−178.17 (16)	C10—C9—C11—C12	2.6 (3)
C2—C3—C4—C5	0.9 (3)	N1—C9—C11—C7	−0.9 (2)
C3—C4—C5—C6	−0.5 (3)	C10—C9—C11—C7	−179.65 (17)
C4—C5—C6—C1	−0.1 (3)	N2—C7—C11—C9	21.5 (2)
C4—C5—C6—C7	−179.88 (16)	C6—C7—C11—C9	−102.35 (18)
C2—C1—C6—C5	0.4 (3)	N2—C7—C11—C12	−160.51 (14)
C2—C1—C6—C7	−179.86 (16)	C6—C7—C11—C12	75.67 (18)
C8—N2—C7—C11	−30.2 (2)	C13—O2—C12—O1	3.2 (3)
C8—N2—C7—C6	93.77 (18)	C13—O2—C12—C11	−179.11 (16)
C5—C6—C7—N2	106.84 (17)	C9—C11—C12—O1	−164.82 (18)
C1—C6—C7—N2	−72.89 (19)	C7—C11—C12—O1	17.3 (2)
C5—C6—C7—C11	−130.15 (16)	C9—C11—C12—O2	17.5 (3)
C1—C6—C7—C11	50.1 (2)	C7—C11—C12—O2	−160.38 (14)
C7—N2—C8—O3	−166.08 (16)	C16—O5—C15—O4	7.2 (12)
C7—N2—C8—N1	16.3 (2)	C16—O5—C15—C14	178.5 (10)
C9—N1—C8—O3	−168.65 (16)	C15—O5—C16—C17	−180.0 (6)
C9—N1—C8—N2	9.1 (2)