Crystal structure of (<i>S</i>)-5-chloro-<i>N</i>-({2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5-yl}methyl)thiophene-2-carboxamide
Shen, Jie; Tang, Gu-Ping; Hu, Xiu-Rong; Acta Crystallographica Section E 74 (2018) 51–54; doi:10.1107/S2056989017017819

data_2242344
_publ_section_title
;
 Crystal structure of
 (<i>S</i>)-5-chloro-<i>N</i>-({2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5-yl}methyl)thiophene-2-carboxamide
;
_journal_coeditor_code           XU5913
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              51
_journal_page_last               54
_journal_paper_doi               10.1107/S2056989017017819
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C19 H18 Cl N3 O5 S'
_chemical_formula_moiety         'C19 H18 Cl N3 O5 S'
_chemical_formula_sum            'C19 H18 Cl N3 O5 S'
_chemical_formula_weight         435.87
_chemical_name_common            rivaroxaban
_chemical_name_systematic
(<i>S</i>)-5-Chloro-<i>N</i>-({2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5-yl}methyl)thiophene-2-carboxamide
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                63.426(2)
_cell_angle_beta                 74.414(3)
_cell_angle_gamma                78.144(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0184(6)
_cell_length_b                   10.9980(8)
_cell_length_c                   11.2386(8)
_cell_measurement_reflns_used    6182
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     955.56(12)
_computing_cell_refinement
;
PROCESS-AUTO (Rigaku, 2006)
;
_computing_data_collection
;
PROCESS-AUTO (Rigaku, 2006)
;
_computing_data_reduction
;
CrystalStructure (Rigaku, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz,
2006)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8375
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.29
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_correction_T_min  0.8683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.475
_refine_ls_abs_structure_details
;
Flack (1983), 2519 Friedel pairs
;
_refine_ls_abs_structure_Flack   -0.07(13)
_refine_ls_extinction_coef       0.0153(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL97 (Sheldrick, 2008)
;
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         6267
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+0.9688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1489
_reflns_number_gt                3981
_reflns_number_total             6267
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            xu5913sup1.cif
_cod_data_source_block           I
_cod_database_code               2242344
_cod_database_fobs_code          2242344