Toward Novel Solid-State Forms of the Anti-HIV Drug Efavirenz: From Low Screening Success to Cocrystals Engineering Strategies and Discovery of a New Polymorph
de Melo, Ariane Carla Campos; de Amorim, Isadora Ferreira; Cirqueira, Marilia de Lima; Martins, Felipe Terra; Crystal Growth & Design 13 (2013) 1558–; doi:10.1021/cg3018002

data_4507576
_publ_section_title
;
 Toward Novel Solid-State Forms of the Anti-HIV Drug Efavirenz: From Low
 Screening Success to Cocrystals Engineering Strategies and Discovery of a
 New Polymorph
;
_journal_issue                   4
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              1558
_journal_paper_doi               10.1021/cg3018002
_journal_volume                  13
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H9 Cl F3 N O2'
_chemical_formula_weight         315.67
_chemical_name_systematic
;
(4S)-6-Chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-
benzoxazin-2-one 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-01-18T18:46:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 113.59(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.656(7)
_cell_length_b                   5.312(2)
_cell_length_c                   17.227(7)
_cell_measurement_reflns_used    1585
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      22.14
_cell_measurement_theta_min      2.456
_cell_volume                     1396.8(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5563
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.31
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Blessing, R. H. (1995) Acta Cryst., A51, 33-38'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2493
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.02
_refine_ls_shift/su_mean         0.014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0302P)^2^+1.4801P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.087
_refine_ls_wR_factor_ref         0.106
_reflns_number_gt                1573
_reflns_number_total             2493
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3018002_si_002.cif
_cod_data_source_block           Efavirenz_Form_V
_cod_original_cell_volume        1396.9(10)
_cod_original_sg_symbol_H-M      C2
_cod_database_code               4507576