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_4519486
_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         'C17.465 H28.396 Cl0.535 N O, Cl, 0.328(H2 O)'
_chemical_formula_sum            'C17.47 H29.05 Cl1.53 N O1.33'
_chemical_formula_weight         328.74
_chemical_name_systematic
;
1-{3-[3-(4-chlorophenyl)propoxy]propyl}piperidin-1-ium 
1-{3-[3-(4-methylphenyl)propoxy]propyl}piperidin-1-ium 
0.54:0.46 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             2023-03-17
_audit_creation_method
;FinalCif V118 by Daniel Kratzert, Freiburg 2023,
https://dkratzert.de/finalcif.html
;
_cell_angle_alpha                90
_cell_angle_beta                 97.601(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1036(5)
_cell_length_b                   8.3072(6)
_cell_length_c                   15.8675(12)
_cell_measurement_reflns_used    5546
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.587
_cell_measurement_theta_min      2.445
_cell_volume                     928.13(12)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (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 0.993
_diffrn_measured_fraction_theta_max 0.978
_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  0.0346
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7178
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.028
_diffrn_reflns_theta_min         2.444
_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    1.675
_exptl_absorpt_correction_T_max  0.3027
_exptl_absorpt_correction_T_min  0.2070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1143 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.6838.
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    1.176
_exptl_crystal_description       Plate
_exptl_crystal_F_000             355
_exptl_crystal_recrystallization_method
'crystallised by liquid diffusion of 1,4-dioxane and DIPE'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.11(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2950
_refine_ls_number_restraints     382
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0639
_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^)+(0.1127P)^2^+0.4054P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1736
_refine_ls_wR_factor_ref         0.1856
_reflns_Friedel_coverage         0.583
_reflns_Friedel_fraction_full    0.685
_reflns_Friedel_fraction_max     0.662
_reflns_number_gt                2516
_reflns_number_total             2950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            Cl_Me_jw25255-finalcif.cif
_cod_data_source_block           jw25255
_cod_database_code               4519486
_cod_database_fobs_code 4519486