#------------------------------------------------------------------------------
#$Date: 2022-04-09 00:56:45 +0300 (Sat, 09 Apr 2022) $
#$Revision: 274432 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/99/7129938.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_7129938
loop_
_publ_author_name
'Mannava, M. K. Chaitanya'
'Bommaka, Manish K.'
'Dandela, Rambabu'
'Solomon, K. Anand'
'Nangia, Ashwini K.'
_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, C7 H3 F O2'
_chemical_formula_sum            'C31 H32 F N2 O5'
_chemical_formula_weight         531.58
_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             2021-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-22 deposited with the CCDC.	2022-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.456(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1975(5)
_cell_length_b                   17.7650(8)
_cell_length_c                   13.5020(6)
_cell_measurement_reflns_used    40373
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.099
_cell_measurement_theta_min      2.160
_cell_volume                     2668.8(2)
_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      293.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  bruker
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            40373
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.099
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_min         2.160
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  25.099
_exptl_absorpt_correction_T_min  2.160
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       needle
_exptl_crystal_F_000             1124
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     486
_refine_ls_number_reflns         4736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0489
_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/[σ²(Fo²)+(0.0658P)²+0.9226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3602
_reflns_number_total             4736
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc07187d2.cif
_cod_data_source_block           nfpd3fbza_0m
_cod_database_code               7129938
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: F00Q(0.6) F29(0.4)
3.a Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.20338(13) 0.55685(8) 0.54843(11) 0.0589(4) Uani 1 1 d . . . . .
C1 C 0.1499(3) 0.61770(15) 0.5966(2) 0.0721(7) Uani 1 1 d . . . . .
H1A H 0.152(2) 0.6642(17) 0.553(2) 0.092(9) Uiso 1 1 d . . . . .
H1B H 0.200(2) 0.6267(15) 0.658(2) 0.086(9) Uiso 1 1 d . . . . .
H1C H 0.063(3) 0.6044(16) 0.607(2) 0.099(9) Uiso 1 1 d . . . . .
O3 O 0.80237(14) 0.23761(9) 0.69365(12) 0.0697(5) Uani 1 1 d . . . . .
C2 C 0.15138(17) 0.53705(11) 0.45573(15) 0.0477(5) Uani 1 1 d . . . . .
C3 C 0.0531(2) 0.57293(12) 0.40563(19) 0.0596(6) Uani 1 1 d . . . . .
H3 H 0.0158(19) 0.6130(13) 0.4378(16) 0.059(6) Uiso 1 1 d . . . . .
N2 N 0.49426(14) 0.34417(9) 0.55449(11) 0.0439(4) Uani 1 1 d . . . . .
H2 H 0.466(2) 0.2926(15) 0.5390(17) 0.072(7) Uiso 1 1 d . . . . .
C4 C 0.0087(2) 0.55044(13) 0.31032(19) 0.0663(6) Uani 1 1 d . . . . .
H4 H -0.063(2) 0.5772(14) 0.2750(19) 0.081(7) Uiso 1 1 d . . . . .
N1 N 0.31072(14) 0.44304(8) 0.46172(11) 0.0456(4) Uani 1 1 d . . . . .
C5 C 0.0617(2) 0.49282(14) 0.26505(19) 0.0660(6) Uani 1 1 d . . . . .
H5 H 0.029(2) 0.4754(15) 0.196(2) 0.087(8) Uiso 1 1 d . . . . .
O2 O 0.55588(17) 0.23089(9) 0.70369(13) 0.0769(5) Uani 1 1 d . . . . .
H2A H 0.5717 0.2078 0.6542 0.115 Uiso 1 1 calc GR . . . .
C6 C 0.1595(2) 0.45633(13) 0.31482(17) 0.0575(5) Uani 1 1 d . . . . .
H6 H 0.1988(19) 0.4179(13) 0.2831(16) 0.061(6) Uiso 1 1 d . . . . .
C7 C 0.20634(17) 0.47698(10) 0.40994(14) 0.0460(5) Uani 1 1 d . . . . .
C9 C 0.4069(2) 0.38424(12) 0.61223(16) 0.0499(5) Uani 1 1 d . . . . .
H9A H 0.3965(18) 0.3557(12) 0.6671(16) 0.051(6) Uiso 1 1 d . . . . .
H9B H 0.4447(18) 0.4316(13) 0.6378(15) 0.052(5) Uiso 1 1 d . . . . .
C8 C 0.29014(19) 0.39938(12) 0.55030(16) 0.0502(5) Uani 1 1 d . . . . .
H8A H 0.2482(18) 0.3517(12) 0.5317(14) 0.051(5) Uiso 1 1 d . . . . .
H8B H 0.2363(18) 0.4288(12) 0.5873(15) 0.051(5) Uiso 1 1 d . . . . .
C11 C 0.50456(19) 0.38362(12) 0.45810(15) 0.0498(5) Uani 1 1 d . . . . .
H11A H 0.5529(19) 0.3503(12) 0.4234(16) 0.056(6) Uiso 1 1 d . . . . .
H11B H 0.5472(18) 0.4306(13) 0.4720(15) 0.054(6) Uiso 1 1 d . . . . .
C10 C 0.38377(19) 0.39799(12) 0.40108(16) 0.0512(5) Uani 1 1 d . . . . .
H10A H 0.3966(19) 0.4274(12) 0.3396(17) 0.061(6) Uiso 1 1 d . . . . .
H10B H 0.3469(18) 0.3503(12) 0.3811(15) 0.050(5) Uiso 1 1 d . . . . .
C12 C 0.61597(19) 0.33815(12) 0.61146(17) 0.0524(5) Uani 1 1 d . . . . .
H12A H 0.645(2) 0.3910(14) 0.6212(17) 0.066(6) Uiso 1 1 d . . . . .
H12B H 0.6674(19) 0.3118(12) 0.5683(16) 0.060(6) Uiso 1 1 d . . . . .
C17 C 1.1265(3) 0.25838(14) 0.7702(2) 0.0798(8) Uani 1 1 d . . . . .
H17 H 1.173(2) 0.2791(15) 0.823(2) 0.077(8) Uiso 1 1 d . . . . .
C13 C 0.6192(2) 0.29902(12) 0.71077(17) 0.0590(5) Uani 1 1 d . . . . .
H13 H 0.5703(17) 0.3234(11) 0.7668(15) 0.047(5) Uiso 1 1 d . . . . .
C14 C 0.7480(2) 0.28953(15) 0.7555(2) 0.0682(7) Uani 1 1 d . . . . .
H14A H 0.791(2) 0.3411(16) 0.7557(19) 0.081(7) Uiso 1 1 d . . . . .
H14B H 0.750(2) 0.2714(15) 0.823(2) 0.084(8) Uiso 1 1 d . . . . .
C15 C 0.9248(2) 0.23274(11) 0.70056(17) 0.0592(6) Uani 1 1 d . . . . .
C16 C 1.0026(3) 0.26441(13) 0.7735(2) 0.0714(7) Uani 1 1 d . . . . .
H16 H 0.974(2) 0.2914(14) 0.8217(18) 0.066(7) Uiso 1 1 d . . . . .
C18 C 1.1722(3) 0.22198(14) 0.6950(2) 0.0721(7) Uani 1 1 d . . . . .
H18 H 1.252(2) 0.2206(14) 0.6888(18) 0.072(7) Uiso 1 1 d . . . . .
C19 C 1.0948(2) 0.18473(12) 0.62075(17) 0.0594(6) Uani 1 1 d . . . . .
C20 C 1.1379(2) 0.14017(16) 0.5460(2) 0.0709(7) Uani 1 1 d . . . . .
H20 H 1.219(2) 0.1378(13) 0.5412(16) 0.064(7) Uiso 1 1 d . . . . .
C21 C 1.0610(2) 0.10074(17) 0.47975(19) 0.0741(7) Uani 1 1 d . . . . .
H21 H 1.099(2) 0.0659(16) 0.428(2) 0.096(9) Uiso 1 1 d . . . . .
C22 C 0.9369(2) 0.10563(15) 0.48317(18) 0.0680(6) Uani 1 1 d . . . . .
H22 H 0.880(2) 0.0770(15) 0.434(2) 0.083(8) Uiso 1 1 d . . . . .
C23 C 0.8910(2) 0.15007(13) 0.55232(16) 0.0582(5) Uani 1 1 d . . . . .
H23 H 0.807(2) 0.1523(11) 0.5531(14) 0.049(5) Uiso 1 1 d . . . . .
C24 C 0.96844(19) 0.18949(11) 0.62363(16) 0.0539(5) Uani 1 1 d . . . . .
O5 O 0.40773(15) 0.21406(8) 0.47647(14) 0.0714(5) Uani 1 1 d . . . . .
O4 O 0.59505(18) 0.18087(12) 0.51057(19) 0.1085(8) Uani 1 1 d . . . . .
F00Q F 0.6170(2) -0.06817(14) 0.34686(17) 0.0802(7) Uani 0.6 1 d . . P . .
F29 F 0.2422(4) -0.0102(2) 0.2915(3) 0.0976(13) Uani 0.4 1 d . . P . .
C25 C 0.4933(2) 0.17041(12) 0.46978(16) 0.0574(5) Uani 1 1 d . . . . .
C26 C 0.46947(19) 0.09789(11) 0.41306(14) 0.0493(5) Uani 1 1 d . . . . .
C27 C 0.5622(2) 0.04830(13) 0.40356(16) 0.0601(6) Uani 1 1 d . . . . .
H27 H 0.640(2) 0.0601(13) 0.4277(17) 0.066(7) Uiso 1 1 d . . . . .
C28 C 0.5381(3) -0.01873(13) 0.35385(16) 0.0700(7) Uani 1 1 d . . . . .
C29 C 0.4257(3) -0.03843(14) 0.31341(17) 0.0734(7) Uani 1 1 d . . . . .
H29 H 0.406(2) -0.0879(14) 0.2788(18) 0.071(7) Uiso 1 1 d . . . . .
C30 C 0.3345(3) 0.01107(14) 0.32344(18) 0.0729(7) Uani 1 1 d . . . . .
C31 C 0.3556(2) 0.07893(13) 0.37205(16) 0.0589(5) Uani 1 1 d . . . . .
H31 H 0.288(2) 0.1151(14) 0.3771(18) 0.075(7) 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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 117.07(19) . . ?
C15 O3 C14 119.48(18) . . ?
O1 C2 C3 124.34(19) . . ?
O1 C2 C7 115.78(17) . . ?
C3 C2 C7 119.86(19) . . ?
C2 C3 C4 120.3(2) . . ?
C11 N2 C9 110.46(15) . . ?
C12 N2 C9 112.21(16) . . ?
C12 N2 C11 109.10(15) . . ?
C5 C4 C3 120.3(2) . . ?
C7 N1 C8 115.36(15) . . ?
C7 N1 C10 115.90(16) . . ?
C10 N1 C8 108.49(15) . . ?
C4 C5 C6 119.8(2) . . ?
C5 C6 C7 121.7(2) . . ?
C2 C7 N1 118.64(17) . . ?
C6 C7 C2 118.05(19) . . ?
C6 C7 N1 123.23(18) . . ?
C8 C9 N2 112.06(17) . . ?
N1 C8 C9 110.12(17) . . ?
N2 C11 C10 111.91(17) . . ?
N1 C10 C11 109.58(17) . . ?
N2 C12 C13 114.91(18) . . ?
C18 C17 C16 121.4(3) . . ?
O2 C13 C12 112.11(19) . . ?
O2 C13 C14 112.61(19) . . ?
C12 C13 C14 109.5(2) . . ?
O3 C14 C13 106.83(19) . . ?
O3 C15 C24 114.12(18) . . ?
C16 C15 O3 125.3(2) . . ?
C16 C15 C24 120.5(2) . . ?
C15 C16 C17 120.1(3) . . ?
C17 C18 C19 120.2(3) . . ?
C18 C19 C24 119.0(2) . . ?
C20 C19 C18 122.6(2) . . ?
C20 C19 C24 118.3(2) . . ?
C21 C20 C19 121.1(2) . . ?
C20 C21 C22 120.2(3) . . ?
C23 C22 C21 120.6(2) . . ?
C22 C23 C24 120.3(2) . . ?
C15 C24 C19 118.5(2) . . ?
C23 C24 C15 122.2(2) . . ?
C23 C24 C19 119.3(2) . . ?
O5 C25 C26 118.4(2) . . ?
O4 C25 O5 124.0(2) . . ?
O4 C25 C26 117.5(2) . . ?
C27 C26 C25 120.1(2) . . ?
C31 C26 C25 121.17(19) . . ?
C31 C26 C27 118.7(2) . . ?
C28 C27 C26 119.3(2) . . ?
F00Q C28 C27 122.6(3) . . ?
F00Q C28 C29 114.6(2) . . ?
C29 C28 C27 122.7(2) . . ?
C28 C29 C30 117.6(2) . . ?
F29 C30 C29 113.9(3) . . ?
F29 C30 C31 124.7(3) . . ?
C29 C30 C31 121.3(3) . . ?
C26 C31 C30 120.5(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.428(3) . ?
O1 C2 1.366(2) . ?
O3 C14 1.426(3) . ?
O3 C15 1.367(3) . ?
C2 C3 1.381(3) . ?
C2 C7 1.409(3) . ?
C3 C4 1.385(3) . ?
N2 C9 1.498(2) . ?
N2 C11 1.494(2) . ?
N2 C12 1.492(3) . ?
C4 C5 1.362(4) . ?
N1 C7 1.426(2) . ?
N1 C8 1.465(2) . ?
N1 C10 1.460(2) . ?
C5 C6 1.380(3) . ?
O2 C13 1.401(3) . ?
C6 C7 1.381(3) . ?
C9 C8 1.495(3) . ?
C11 C10 1.501(3) . ?
C12 C13 1.507(3) . ?
C17 C16 1.398(4) . ?
C17 C18 1.352(4) . ?
C13 C14 1.509(3) . ?
C15 C16 1.360(3) . ?
C15 C24 1.422(3) . ?
C18 C19 1.414(3) . ?
C19 C20 1.410(4) . ?
C19 C24 1.422(3) . ?
C20 C21 1.364(4) . ?
C21 C22 1.398(4) . ?
C22 C23 1.366(3) . ?
C23 C24 1.408(3) . ?
O5 C25 1.244(3) . ?
O4 C25 1.223(3) . ?
F00Q C28 1.257(3) . ?
F29 C30 1.139(4) . ?
C25 C26 1.507(3) . ?
C26 C27 1.379(3) . ?
C26 C31 1.374(3) . ?
C27 C28 1.379(3) . ?
C28 C29 1.360(4) . ?
C29 C30 1.366(4) . ?
C30 C31 1.380(3) . ?
