Crystal structure of pirfenidone (5-methyl-1-phenyl-1<i>H</i>-pyridin-2-one): an active pharmaceutical ingredient (API)
Barbero, Mauro; Mossotti, Matteo; Sironi, Angelo; Giovenzana, Giovanni Battista; Colombo, Valentina; Acta Crystallographica Section E 75 (2019) 984–986; doi:10.1107/S2056989019006418

data_2242976
_publ_section_title
;
 Crystal structure of pirfenidone
 (5-methyl-1-phenyl-1<i>H</i>-pyridin-2-one): an active pharmaceutical
 ingredient (API)
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              984
_journal_page_last               986
_journal_paper_doi               10.1107/S2056989019006418
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C12 H11 N O'
_chemical_formula_moiety         'C12 H11 N O'
_chemical_formula_sum            'C12 H11 N O'
_chemical_formula_weight         185.22
_chemical_melting_point          375
_chemical_name_common            Pirfenidone
_chemical_name_systematic
;
5-Methyl-1-phenylpyridin-2(1<i>H</i>)-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 104.744(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2525(8)
_cell_length_b                   7.7970(10)
_cell_length_c                   10.2810(13)
_cell_measurement_reflns_used    2547
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.173
_cell_measurement_theta_min      3.3205
_cell_volume                     484.70(11)
_computing_cell_refinement
;
SAINT (Bruker, 2010)
;
_computing_data_collection
;
APEX2 (Bruker, 2010)
;
_computing_data_reduction
;
SAINT (Bruker, 2010)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae <i>et al.</i>,
2008)
;
_computing_publication_material
;
SHELXL2017 (Sheldrick, 2015b), PLATON (Spek, 2009) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2017 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4547
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.202
_diffrn_reflns_theta_min         2.048
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2010)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       plate
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.197
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 762 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2128
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0370
_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/[\s^2^(Fo^2^)+(0.0528P)^2^+0.0476P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0954
_reflns_number_gt                1879
_reflns_number_total             2128
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            tx2011sup1.cif
_cod_data_source_block           Pirfenidone
_cod_database_code               2242976
_shelx_hkl_checksum              42049
_shelx_res_checksum              81682