Exploring Polymorphism: Hydrochloride Salts of Pitolisant and Analogues
Patel, Jessica; Leduc, Zachary; Numez Avila, Aaron Gabriel; Glover, Joseph A.; Wu, Kelin; Zhang, Yuxing; Zhang, Jing; Zhai, Xiaoting; Jing, Huize; Chen, Alex M.; Chartrand, Daniel; Maris, Thierry; Day, Graeme M.; Wuest, James D.; Crystal Growth & Design 24 (2024) 1268–1283; doi:10.1021/acs.cgd.3c01245

data_4519480
_publ_section_title
;
 Exploring Polymorphism: Hydrochloride Salts of Pitolisant and Analogues
;
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1268
_journal_page_last               1283
_journal_paper_doi               10.1021/acs.cgd.3c01245
_journal_volume                  24
_journal_year                    2024
_chemical_formula_moiety         'C17 H27 Cl0.13 F0.87 N O, Cl'
_chemical_formula_sum            'C17 H27 Cl1.13 F0.87 N O'
_chemical_formula_weight         317.98
_chemical_name_systematic
;
1-{3-[3-(4-fluorophenyl)propoxy]propyl}piperidin-1-ium 
1-{3-[3-(4-chlorophenyl)propoxy]propyl}piperidin-1-ium 
0.87:0.43 chloride
;
_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   geom
_atom_sites_solution_primary     dual
_audit_contact_author_name
;
;
_audit_creation_date             2023-03-14
_audit_creation_method
;FinalCif V118 by Daniel Kratzert, Freiburg 2023,
https://dkratzert.de/finalcif.html
;
_cell_angle_alpha                90
_cell_angle_beta                 111.488(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.5940(16)
_cell_length_b                   8.1331(8)
_cell_length_c                   14.2527(12)
_cell_measurement_reflns_used    4754
_cell_measurement_temperature    150
_cell_measurement_theta_max      50.778
_cell_measurement_theta_min      2.490
_cell_volume                     1789.9(3)
_computing_cell_refinement
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 4 (2022) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16976
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.035
_diffrn_reflns_theta_min         2.490
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.1994564
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.74
_exptl_absorpt_coefficient_mu    1.401
_exptl_absorpt_correction_T_max  0.1123
_exptl_absorpt_correction_T_min  0.0267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1437 before and 0.0877 after correction.
The Ratio of minimum to maximum transmission is 0.2378.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       Plate
_exptl_crystal_F_000             684
_exptl_crystal_recrystallization_method
'mixed crystals obtained by liquid diffusion of 1,4 dioxane in DIPE'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3351
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.1551
_refine_ls_R_factor_gt           0.0980
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2817
_refine_ls_wR_factor_ref         0.3441
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1661
_reflns_number_total             3351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            Cl_F_jw25223-finalcif.cif
_cod_data_source_block           jw25223
_cod_database_code               4519480
_cod_database_fobs_code 4519480