#------------------------------------------------------------------------------
#$Date: 2020-07-24 07:45:36 +0300 (Fri, 24 Jul 2020) $
#$Revision: 254539 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022207.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022207
loop_
_publ_author_name
'Cleetus, Annie'
'Rani, Gulshan'
'Dharma Rao, G. B.'
'Chopra, Deepak'
_publ_section_title
;
 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
;
_journal_coeditor_code           CU3165
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620009560
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C13 H13 F N2 O3'
_chemical_formula_moiety         'C13 H13 F N2 O3'
_chemical_formula_sum            'C13 H13 F N2 O3'
_chemical_formula_weight         264.25
_chemical_name_systematic
;
Methyl
4-(4-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 108.838(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.0881(15)
_cell_length_b                   7.1958(8)
_cell_length_c                   23.177(3)
_cell_measurement_reflns_used    7891
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      29.85
_cell_measurement_theta_min      2.68
_cell_volume                     2539.4(5)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2020) and PARST
(Nardelli, 1995)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015) and
WinGX (Farrugia (2012)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008) and
SIR2014 (Burla et al., 2015)
;
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            24306
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.138
_diffrn_reflns_theta_min         2.675
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2001)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0511P)²+1.7817P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1145
_reflns_number_gt                2706
_reflns_number_total             3737
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cu3165sup1.cif
_cod_data_source_block           F1
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2022207
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.02856(6) 0.28689(14) 0.08155(5) 0.0212(2) Uani d 1 . .
O O2 -0.04829(6) 0.08374(13) 0.11713(4) 0.0183(2) Uani d 1 . .
O O3 0.19561(6) -0.43566(13) 0.02354(4) 0.0159(2) Uani d 1 . .
F F1 0.42399(6) 0.14688(16) 0.28731(4) 0.0366(3) Uani d 1 . .
N N1 0.09065(7) -0.34590(17) 0.06405(5) 0.0128(2) Uani d 1 . .
H H1A 0.0744(10) -0.464(3) 0.0647(7) 0.020(4) Uiso d 1 . .
N N2 0.17380(7) -0.12694(16) 0.03515(5) 0.0126(2) Uani d 1 . .
H H2A 0.2153(11) -0.100(2) 0.0197(8) 0.022(4) Uiso d 1 . .
C C1 0.27321(9) 0.2129(2) 0.13482(6) 0.0173(3) Uani d 1 . .
H H1 0.263082 0.297493 0.101788 0.021 Uiso calc 1 . .
C C2 0.34316(9) 0.2433(2) 0.18837(7) 0.0229(3) Uani d 1 . .
H H2 0.381219 0.346839 0.192147 0.027 Uiso calc 1 . .
C C3 0.35521(9) 0.1195(2) 0.23523(6) 0.0233(3) Uani d 1 . .
C C4 0.30157(9) -0.0309(2) 0.23263(6) 0.0231(3) Uani d 1 . .
H H4 0.311358 -0.112770 0.266334 0.028 Uiso calc 1 . .
C C5 0.23225(9) -0.0593(2) 0.17878(6) 0.0190(3) Uani d 1 . .
H H5 0.193881 -0.161917 0.175722 0.023 Uiso calc 1 . .
C C6 0.21849(8) 0.06081(19) 0.12938(5) 0.0129(3) Uani d 1 . .
C C7 0.14667(8) 0.02117(18) 0.06901(5) 0.0112(2) Uani d 1 . .
H H7 0.136980 0.136887 0.043813 0.013 Uiso calc 1 . .
C C8 0.15738(8) -0.30750(19) 0.04046(5) 0.0125(3) Uani d 1 . .
C C9 0.03494(8) -0.21130(18) 0.07407(5) 0.0117(3) Uani d 1 . .
C C10 -0.04937(8) -0.28875(19) 0.07810(6) 0.0140(3) Uani d 1 . .
H H10A -0.039157 -0.343228 0.118554 0.021 Uiso calc 1 . .
H H10B -0.071249 -0.384804 0.046890 0.021 Uiso calc 1 . .
H H10C -0.092884 -0.188923 0.071487 0.021 Uiso calc 1 . .
C C11 0.06014(8) -0.03197(19) 0.07743(5) 0.0115(3) Uani d 1 . .
C C12 0.01232(8) 0.12709(19) 0.09088(6) 0.0131(3) Uani d 1 . .
C C13 -0.09595(10) 0.2391(2) 0.13041(7) 0.0243(3) Uani d 1 . .
H H13A -0.055451 0.318714 0.161158 0.036 Uiso calc 1 . .
H H13B -0.141964 0.193158 0.145987 0.036 Uiso calc 1 . .
H H13C -0.122776 0.310988 0.093100 0.036 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 O2 C13 . . 115.48(11) ?
C8 N1 C9 . . 123.55(12) ?
C8 N1 H1A . . 117.9(10) ?
C9 N1 H1A . . 117.0(10) ?
C8 N2 C7 . . 123.53(11) ?
C8 N2 H2A . . 116.7(11) ?
C7 N2 H2A . . 117.2(11) ?
C6 C1 C2 . . 120.71(13) ?
C6 C1 H1 . . 119.6 ?
C2 C1 H1 . . 119.6 ?
C3 C2 C1 . . 118.00(14) ?
C3 C2 H2 . . 121.0 ?
C1 C2 H2 . . 121.0 ?
F1 C3 C2 . . 118.34(14) ?
F1 C3 C4 . . 118.16(14) ?
C2 C3 C4 . . 123.50(13) ?
C3 C4 C5 . . 117.68(13) ?
C3 C4 H4 . . 121.2 ?
C5 C4 H4 . . 121.2 ?
C6 C5 C4 . . 120.87(13) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C1 C6 C5 . . 119.20(12) ?
C1 C6 C7 . . 120.13(11) ?
C5 C6 C7 . . 120.61(12) ?
N2 C7 C11 . . 109.21(10) ?
N2 C7 C6 . . 110.93(10) ?
C11 C7 C6 . . 112.58(10) ?
N2 C7 H7 . . 108.0 ?
C11 C7 H7 . . 108.0 ?
C6 C7 H7 . . 108.0 ?
O3 C8 N2 . . 124.02(11) ?
O3 C8 N1 . . 120.31(12) ?
N2 C8 N1 . . 115.60(11) ?
C11 C9 N1 . . 118.64(11) ?
C11 C9 C10 . . 127.93(12) ?
N1 C9 C10 . . 113.41(11) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C9 C11 C12 . . 126.21(11) ?
C9 C11 C7 . . 120.39(11) ?
C12 C11 C7 . . 113.38(11) ?
O1 C12 O2 . . 122.04(12) ?
O1 C12 C11 . . 122.90(11) ?
O2 C12 C11 . . 114.99(11) ?
O2 C13 H13A . . 109.5 ?
O2 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O2 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C12 . 1.2140(17) ?
O2 C12 . 1.3422(15) ?
O2 C13 . 1.4441(17) ?
O3 C8 . 1.2403(16) ?
F1 C3 . 1.3630(15) ?
N1 C8 . 1.3809(16) ?
N1 C9 . 1.3890(17) ?
N1 H1A . 0.891(18) ?
N2 C8 . 1.3395(18) ?
N2 C7 . 1.4709(17) ?
N2 H2A . 0.875(17) ?
C1 C6 . 1.3845(19) ?
C1 C2 . 1.3975(19) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.370(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.373(2) ?
C4 C5 . 1.3943(18) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3943(19) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.5265(16) ?
C7 C11 . 1.5158(17) ?
C7 H7 . 1.0000 ?
C9 C11 . 1.3473(19) ?
C9 C10 . 1.4970(17) ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 C12 . 1.4676(18) ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.6(2) ?
C1 C2 C3 F1 . . . . 179.16(12) ?
C1 C2 C3 C4 . . . . -1.0(2) ?
F1 C3 C4 C5 . . . . -179.00(13) ?
C2 C3 C4 C5 . . . . 1.1(2) ?
C3 C4 C5 C6 . . . . 0.3(2) ?
C2 C1 C6 C5 . . . . 2.0(2) ?
C2 C1 C6 C7 . . . . -175.37(12) ?
C4 C5 C6 C1 . . . . -1.8(2) ?
C4 C5 C6 C7 . . . . 175.52(12) ?
C8 N2 C7 C11 . . . . -33.69(16) ?
C8 N2 C7 C6 . . . . 90.96(14) ?
C1 C6 C7 N2 . . . . 100.88(14) ?
C5 C6 C7 N2 . . . . -76.42(15) ?
C1 C6 C7 C11 . . . . -136.40(13) ?
C5 C6 C7 C11 . . . . 46.31(16) ?
C7 N2 C8 O3 . . . . -163.16(11) ?
C7 N2 C8 N1 . . . . 19.72(17) ?
C9 N1 C8 O3 . . . . -168.46(11) ?
C9 N1 C8 N2 . . . . 8.77(17) ?
C8 N1 C9 C11 . . . . -19.04(18) ?
C8 N1 C9 C10 . . . . 159.33(11) ?
N1 C9 C11 C12 . . . . -176.58(11) ?
C10 C9 C11 C12 . . . . 5.3(2) ?
N1 C9 C11 C7 . . . . 1.35(17) ?
C10 C9 C11 C7 . . . . -176.76(11) ?
N2 C7 C11 C9 . . . . 21.92(15) ?
C6 C7 C11 C9 . . . . -101.77(13) ?
N2 C7 C11 C12 . . . . -159.91(10) ?
C6 C7 C11 C12 . . . . 76.41(13) ?
C13 O2 C12 O1 . . . . 3.22(18) ?
C13 O2 C12 C11 . . . . -179.83(11) ?
C9 C11 C12 O1 . . . . -164.90(13) ?
C7 C11 C12 O1 . . . . 17.05(17) ?
C9 C11 C12 O2 . . . . 18.17(18) ?
C7 C11 C12 O2 . . . . -159.88(10) ?

_cod_database_fobs_code 2022207
