#------------------------------------------------------------------------------
#$Date: 2019-11-23 22:17:26 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235329 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/68/4036847.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4036847
loop_
_publ_author_name
'Kise, Naoki'
'Hamada, Yusuke'
'Sakurai, Toshihiko'
_publ_section_title
;
 Electroreductive Intermolecular Coupling of Uracils with Aromatic
 Ketones: Synthesis of 6-Substituted and cis-5,6-Disubstituted
 5,6-Dihydro-1,3-dimethyluracils and Their Transformation to 6-Substituted
 1,3-Dimethyluracils, trans-5,6-Disubstituted
 5,6-Dihydro-1,3-dimethyluracils, and 4,5,5-Trisubstituted
 3-Methyloxazolizin-2-ones.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5101
_journal_page_last               5119
_journal_paper_doi               10.1021/acs.joc.6b00670
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C19 H17 F3 N2 O3'
_chemical_formula_sum            'C19 H17 F3 N2 O3'
_chemical_formula_weight         378.35
_chemical_melting_point          494.5(5)
_chemical_name_systematic
; 
(R*)-2-((S*)-5,5-bis(4-fluorophenyl)-3-methyl-2-oxooxazolidin-4-yl)-2-
fluoro-N-methylacetamide
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 84.55(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.394(3)
_cell_length_b                   24.341(7)
_cell_length_c                   9.028(3)
_cell_measurement_reflns_used    16541
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.2
_cell_volume                     1836.2(10)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_publication_material  yadokari-XG
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17848
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9722
_exptl_absorpt_correction_T_min  0.9455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0594P)²+0.3496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1295
_reflns_number_gt                3192
_reflns_number_total             4200
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00670_si_019.cif
_cod_data_source_block           threo12l
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '494-495' was changed to
'494.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               4036847
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.20086(13) 0.38283(5) 0.39680(11) 0.0472(3) Uani 1 1 d .
C1 C 0.2033(2) 0.43080(8) 0.47398(19) 0.0555(4) Uani 1 1 d .
O2 O 0.1376(2) 0.43582(7) 0.59785(15) 0.0876(5) Uani 1 1 d .
N1 N 0.28850(18) 0.46863(6) 0.39146(16) 0.0520(4) Uani 1 1 d .
C2 C 0.3079(3) 0.52477(8) 0.4436(3) 0.0807(7) Uani 1 1 d .
H1 H 0.2133 0.5456 0.4298 0.121 Uiso 1 1 calc R
H2 H 0.3984 0.5414 0.3879 0.121 Uiso 1 1 calc R
H3 H 0.3247 0.5243 0.5473 0.121 Uiso 1 1 calc R
C3 C 0.32771(18) 0.44914(6) 0.23999(16) 0.0400(3) Uani 1 1 d .
H4 H 0.4358 0.4609 0.2028 0.048 Uiso 1 1 calc R
C4 C 0.2063(2) 0.46925(6) 0.13627(18) 0.0465(4) Uani 1 1 d .
H5 H 0.2257 0.4497 0.0413 0.056 Uiso 1 1 calc R
F1 F 0.05191(12) 0.45661(4) 0.19849(13) 0.0651(3) Uani 1 1 d .
C5 C 0.2228(2) 0.53041(7) 0.10649(18) 0.0482(4) Uani 1 1 d .
O3 O 0.34898(17) 0.54677(5) 0.04246(17) 0.0742(4) Uani 1 1 d .
N2 N 0.1000(2) 0.56213(6) 0.15176(17) 0.0557(4) Uani 1 1 d .
C6 C 0.1070(3) 0.62162(8) 0.1363(3) 0.0859(7) Uani 1 1 d .
H6 H 0.2107 0.6344 0.1573 0.129 Uiso 1 1 calc R
H7 H 0.0264 0.6381 0.2048 0.129 Uiso 1 1 calc R
H8 H 0.0886 0.6316 0.0364 0.129 Uiso 1 1 calc R
C7 C 0.32530(17) 0.38632(6) 0.27271(15) 0.0365(3) Uani 1 1 d .
C8 C 0.48124(18) 0.36593(6) 0.33030(15) 0.0367(3) Uani 1 1 d .
C9 C 0.63083(19) 0.38198(6) 0.26762(18) 0.0462(4) Uani 1 1 d .
H9 H 0.6389 0.4068 0.1889 0.055 Uiso 1 1 calc R
C10 C 0.7689(2) 0.36158(7) 0.3204(2) 0.0531(4) Uani 1 1 d .
H10 H 0.8693 0.3728 0.2789 0.064 Uiso 1 1 calc R
C11 C 0.7541(2) 0.32468(7) 0.43501(19) 0.0513(4) Uani 1 1 d .
F2 F 0.88871(14) 0.30475(5) 0.48876(14) 0.0765(4) Uani 1 1 d .
C12 C 0.6088(2) 0.30635(8) 0.4968(2) 0.0603(5) Uani 1 1 d .
H11 H 0.6021 0.2803 0.5725 0.072 Uiso 1 1 calc R
C13 C 0.4725(2) 0.32739(7) 0.44442(18) 0.0527(4) Uani 1 1 d .
H12 H 0.3728 0.3156 0.4862 0.063 Uiso 1 1 calc R
C14 C 0.28148(18) 0.34908(6) 0.14888(16) 0.0380(3) Uani 1 1 d .
C15 C 0.3595(2) 0.35484(7) 0.00670(17) 0.0495(4) Uani 1 1 d .
H13 H 0.4336 0.3829 -0.0131 0.059 Uiso 1 1 calc R
C16 C 0.3268(3) 0.31877(8) -0.1056(2) 0.0654(5) Uani 1 1 d .
H14 H 0.3770 0.3227 -0.2014 0.078 Uiso 1 1 calc R
C17 C 0.2191(3) 0.27734(8) -0.0721(2) 0.0708(6) Uani 1 1 d .
F3 F 0.1897(2) 0.24202(6) -0.18322(17) 0.1166(6) Uani 1 1 d .
C18 C 0.1426(3) 0.26980(8) 0.0657(3) 0.0684(6) Uani 1 1 d .
H15 H 0.0710 0.2409 0.0845 0.082 Uiso 1 1 calc R
C19 C 0.1734(2) 0.30610(6) 0.1775(2) 0.0507(4) Uani 1 1 d .
H16 H 0.1216 0.3018 0.2725 0.061 Uiso 1 1 calc R
H17 H 0.024(3) 0.5476(8) 0.206(2) 0.060(6) Uiso 1 1 d .
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
C1 O1 C7 107.37(12)
O2 C1 N1 128.04(18)
O2 C1 O1 122.29(19)
N1 C1 O1 109.67(13)
C1 N1 C3 110.96(13)
C1 N1 C2 122.12(16)
C3 N1 C2 125.88(16)
N1 C2 H1 109.5
N1 C2 H2 109.5
H1 C2 H2 109.5
N1 C2 H3 109.5
H1 C2 H3 109.5
H2 C2 H3 109.5
N1 C3 C4 111.52(13)
N1 C3 C7 98.30(11)
C4 C3 C7 115.68(12)
N1 C3 H4 110.3
C4 C3 H4 110.3
C7 C3 H4 110.3
F1 C4 C5 110.66(13)
F1 C4 C3 109.28(13)
C5 C4 C3 111.59(13)
F1 C4 H5 108.4
C5 C4 H5 108.4
C3 C4 H5 108.4
O3 C5 N2 124.79(16)
O3 C5 C4 117.61(14)
N2 C5 C4 117.60(15)
C5 N2 C6 121.89(17)
C5 N2 H17 117.3(13)
C6 N2 H17 119.7(13)
N2 C6 H6 109.5
N2 C6 H7 109.5
H6 C6 H7 109.5
N2 C6 H8 109.5
H6 C6 H8 109.5
H7 C6 H8 109.5
O1 C7 C14 109.03(12)
O1 C7 C8 106.99(11)
C14 C7 C8 109.37(11)
O1 C7 C3 101.43(11)
C14 C7 C3 116.63(12)
C8 C7 C3 112.67(12)
C9 C8 C13 118.40(14)
C9 C8 C7 122.67(13)
C13 C8 C7 118.83(13)
C8 C9 C10 120.93(15)
C8 C9 H9 119.5
C10 C9 H9 119.5
C11 C10 C9 118.48(16)
C11 C10 H10 120.8
C9 C10 H10 120.8
F2 C11 C10 119.04(16)
F2 C11 C12 118.48(16)
C10 C11 C12 122.48(16)
C11 C12 C13 118.44(16)
C11 C12 H11 120.8
C13 C12 H11 120.8
C12 C13 C8 121.22(16)
C12 C13 H12 119.4
C8 C13 H12 119.4
C15 C14 C19 119.21(14)
C15 C14 C7 119.72(13)
C19 C14 C7 120.86(13)
C16 C15 C14 120.14(17)
C16 C15 H13 119.9
C14 C15 H13 119.9
C17 C16 C15 118.45(18)
C17 C16 H14 120.8
C15 C16 H14 120.8
C18 C17 F3 119.1(2)
C18 C17 C16 123.19(17)
F3 C17 C16 117.7(2)
C17 C18 C19 118.49(18)
C17 C18 H15 120.8
C19 C18 H15 120.8
C18 C19 C14 120.50(18)
C18 C19 H16 119.7
C14 C19 H16 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.361(2)
O1 C7 1.4598(17)
C1 O2 1.205(2)
C1 N1 1.347(2)
N1 C3 1.455(2)
N1 C2 1.459(2)
C2 H1 0.9600
C2 H2 0.9600
C2 H3 0.9600
C3 C4 1.528(2)
C3 C7 1.5571(19)
C3 H4 0.9800
C4 F1 1.397(2)
C4 C5 1.517(2)
C4 H5 0.9800
C5 O3 1.224(2)
C5 N2 1.322(2)
N2 C6 1.455(2)
N2 H17 0.84(2)
C6 H6 0.9600
C6 H7 0.9600
C6 H8 0.9600
C7 C14 1.511(2)
C7 C8 1.536(2)
C8 C9 1.384(2)
C8 C13 1.390(2)
C9 C10 1.386(2)
C9 H9 0.9300
C10 C11 1.367(2)
C10 H10 0.9300
C11 F2 1.361(2)
C11 C12 1.367(3)
C12 C13 1.378(3)
C12 H11 0.9300
C13 H12 0.9300
C14 C15 1.391(2)
C14 C19 1.393(2)
C15 C16 1.388(2)
C15 H13 0.9300
C16 C17 1.369(3)
C16 H14 0.9300
C17 C18 1.357(3)
C17 F3 1.361(2)
C18 C19 1.385(3)
C18 H15 0.9300
C19 H16 0.9300
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
C7 O1 C1 O2 -164.58(18)
C7 O1 C1 N1 14.90(18)
O2 C1 N1 C3 -171.41(19)
O1 C1 N1 C3 9.16(19)
O2 C1 N1 C2 -2.5(3)
O1 C1 N1 C2 178.08(16)
C1 N1 C3 C4 95.08(16)
C2 N1 C3 C4 -73.3(2)
C1 N1 C3 C7 -26.81(16)
C2 N1 C3 C7 164.78(17)
N1 C3 C4 F1 -51.59(17)
C7 C3 C4 F1 59.61(16)
N1 C3 C4 C5 71.13(17)
C7 C3 C4 C5 -177.67(12)
F1 C4 C5 O3 -175.08(16)
C3 C4 C5 O3 63.0(2)
F1 C4 C5 N2 5.0(2)
C3 C4 C5 N2 -116.93(17)
O3 C5 N2 C6 -3.5(3)
C4 C5 N2 C6 176.41(18)
C1 O1 C7 C14 -154.21(12)
C1 O1 C7 C8 87.62(14)
C1 O1 C7 C3 -30.61(15)
N1 C3 C7 O1 33.14(13)
C4 C3 C7 O1 -85.64(14)
N1 C3 C7 C14 151.40(12)
C4 C3 C7 C14 32.62(18)
N1 C3 C7 C8 -80.91(14)
C4 C3 C7 C8 160.31(12)
O1 C7 C8 C9 -154.72(13)
C14 C7 C8 C9 87.33(16)
C3 C7 C8 C9 -44.10(18)
O1 C7 C8 C13 29.04(17)
C14 C7 C8 C13 -88.91(16)
C3 C7 C8 C13 139.66(14)
C13 C8 C9 C10 -2.1(2)
C7 C8 C9 C10 -178.37(14)
C8 C9 C10 C11 0.7(3)
C9 C10 C11 F2 -179.39(15)
C9 C10 C11 C12 1.5(3)
F2 C11 C12 C13 178.69(16)
C10 C11 C12 C13 -2.2(3)
C11 C12 C13 C8 0.7(3)
C9 C8 C13 C12 1.4(3)
C7 C8 C13 C12 177.81(16)
O1 C7 C14 C15 164.66(13)
C8 C7 C14 C15 -78.67(16)
C3 C7 C14 C15 50.62(19)
O1 C7 C14 C19 -20.62(19)
C8 C7 C14 C19 96.04(16)
C3 C7 C14 C19 -134.67(15)
C19 C14 C15 C16 1.4(2)
C7 C14 C15 C16 176.20(15)
C14 C15 C16 C17 -1.1(3)
C15 C16 C17 C18 0.0(3)
C15 C16 C17 F3 -179.37(17)
F3 C17 C18 C19 -179.87(18)
C16 C17 C18 C19 0.7(3)
C17 C18 C19 C14 -0.4(3)
C15 C14 C19 C18 -0.6(2)
C7 C14 C19 C18 -175.37(15)
