Fluorobenzoic acid coformers to improve the solubility and permeability of the BCS class IV drug naftopidil
Mannava, M. K. Chaitanya; Bommaka, Manish K.; Dandela, Rambabu; Solomon, K. Anand; Nangia, Ashwini K.; Chemical Communications  (2022) –; doi:10.1039/D1CC07187D

data_7129944
_publ_section_title
;
 Fluorobenzoic acid coformers to improve the solubility and permeability
 of the BCS class IV drug naftopidil
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC07187D
_journal_year                    2022
_chemical_formula_moiety         'C24 H29 N2 O3, C6.99 H1.99 F2.04 O2'
_chemical_formula_sum            'C30.99 H30.99 F2.04 N2 O5'
_chemical_formula_weight         550.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-04-24
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2021-12-22 deposited with the CCDC.	2022-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.629(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0504(6)
_cell_length_b                   17.8882(9)
_cell_length_c                   13.3766(6)
_cell_measurement_reflns_used    9261
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.28
_cell_measurement_theta_min      3.21
_cell_volume                     2626.5(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            142326
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         45.410
_diffrn_reflns_theta_min         1.909
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7489
_exptl_absorpt_correction_T_min  0.5659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1259 before and 0.0652 after correction. The Ratio of minimum to maximum transmission is 0.7556. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       block
_exptl_crystal_F_000             1157
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         21885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0664
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+1.2441P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.1864
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15915
_reflns_number_total             21885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc07187d2.cif
_cod_data_source_block           platon_pl_CCDC2
_cod_database_code               7129944
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C25(0.5) C26(0.5) C27(0.5) H27(0.5) C28(0.5) C30(0.75) H30(0.75)
 C31(0.5) F0AA(0.5) C0AA(0.5) F3(0.5) C1AA(0.5) C(0.5) C2AA(0.23878)
 H2AA(0.23878) C3AA(0.5) H3AA(0.5) C4AA(0.5) F1AA(0.25)
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C18(H18A,H18B), C19(H19A,
 H19B)
3.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C20(H20), C21(H21), C22(H22), C24(H24), C27(H27), C30(H30), C2AA(H2AA),
 C3AA(H3AA)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'