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_4519489
_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_absolute_configuration ad
_chemical_formula_moiety         'C17 H27 Br N O, Cl, 0.44(H2 O)'
_chemical_formula_sum            'C17 H27.87 Br Cl N O1.43'
_chemical_formula_weight         384.59
_chemical_name_systematic
;
1-{3-[3-(4-bromophenyl)propoxy]propyl}piperidin-1-ium chloride hydrate
;
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_contact_author_name
;
;
_audit_creation_date             2023-02-23
_audit_creation_method
;FinalCif V117 by Daniel Kratzert, Freiburg 2023,
https://dkratzert.de/finalcif.html
;
_cell_angle_alpha                90
_cell_angle_beta                 98.369(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1158(4)
_cell_length_b                   8.3038(6)
_cell_length_c                   16.0142(11)
_cell_measurement_reflns_used    4434
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.730
_cell_measurement_theta_min      2.427
_cell_volume                     936.17(11)
_computing_cell_refinement
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 3 (2019) 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    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.994
_diffrn_measured_fraction_theta_max 0.979
_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  0.0468
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.979
_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       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7347
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.157
_diffrn_reflns_theta_min         2.426
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.1993706
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_exptl_absorpt_coefficient_mu    2.858
_exptl_absorpt_correction_T_max  0.3329
_exptl_absorpt_correction_T_min  0.1984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1228 before and 0.0758 after correction.
The Ratio of minimum to maximum transmission is 0.5960.
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    1.364
_exptl_crystal_description       Plate
_exptl_crystal_F_000             401
_exptl_crystal_recrystallization_method 'liquid diffusion of 1,4-dioxane/DIPE'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.14(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3225
_refine_ls_number_restraints     234
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0573
_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^)+(0.0941P)^2^+0.5046P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1701
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.828
_reflns_Friedel_fraction_max     0.796
_reflns_number_gt                2462
_reflns_number_total             3225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            Br-jw25181-finalcif.cif
_cod_data_source_block           jw25181
_cod_database_code               4519489
_cod_database_fobs_code 4519489