#------------------------------------------------------------------------------ #$Date: 2024-04-11 21:13:54 +0100 (Thu, 11 Apr 2024) $ #$Revision: 291183 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519487.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_4519487 loop_ _publ_author_name '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.' _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 F N O, Cl' _chemical_formula_sum 'C17 H27 Cl F N O' _chemical_formula_weight 315.84 _chemical_name_systematic ; 1-{3-[3-(4-fluorophenyl)propoxy]propyl}piperidin-1-ium 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 2023-02-23 _audit_creation_method ;FinalCif V117 by Daniel Kratzert, Freiburg 2023, https://dkratzert.de/finalcif.html ; _cell_angle_alpha 90 _cell_angle_beta 112.288(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.544(3) _cell_length_b 8.0887(14) _cell_length_c 14.229(2) _cell_measurement_reflns_used 4579 _cell_measurement_temperature 150 _cell_measurement_theta_max 54.721 _cell_measurement_theta_min 2.512 _cell_volume 1761.9(5) _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 '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 0.983 _diffrn_measured_fraction_theta_max 0.973 _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 0.0803 _diffrn_reflns_av_unetI/netI 0.0655 _diffrn_reflns_Laue_measured_fraction_full 0.983 _diffrn_reflns_Laue_measured_fraction_max 0.973 _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 15039 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.973 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.956 _diffrn_reflns_theta_min 2.511 _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 1.310 _exptl_absorpt_correction_T_max 0.3679 _exptl_absorpt_correction_T_min 0.2161 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1321 before and 0.0834 after correction. The Ratio of minimum to maximum transmission is 0.5874. 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 1.191 _exptl_crystal_description Plate _exptl_crystal_F_000 680 _exptl_crystal_recrystallization_method 'crystallised by liqid diffusion with 1,4-dioxane/DIPE' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.920 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.080 _refine_ls_extinction_coef 0.0065(14) _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 1.070 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 3265 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.070 _refine_ls_R_factor_all 0.1425 _refine_ls_R_factor_gt 0.0838 _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^)+(0.1372P)^2^+1.3576P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2270 _refine_ls_wR_factor_ref 0.2766 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1852 _reflns_number_total 3265 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file F-jw25111-finalcif.cif _cod_data_source_block jw25111 _cod_database_code 4519487 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 '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 N1 N 0.5438(3) 0.2407(4) 0.8977(3) 0.0585(11) Uani 1 1 d . . . . . H1 H 0.553538 0.237875 0.971466 0.070 Uiso 1 1 calc R U . . . C1 C 0.1773(4) 0.2152(6) 0.6758(4) 0.0732(15) Uani 1 1 d . . . . . H1A H 0.141382 0.251641 0.714037 0.088 Uiso 1 1 calc R U . . . H1B H 0.175773 0.092962 0.672656 0.088 Uiso 1 1 calc R U . . . F1 F -0.1351(2) 0.4931(5) 0.1244(3) 0.1072(12) Uani 1 1 d . . . . . O1 O 0.2637(2) 0.2691(4) 0.7259(3) 0.0705(10) Uani 1 1 d . . . . . C2 C 0.1400(4) 0.2859(6) 0.5691(4) 0.0755(15) Uani 1 1 d . . . . . H2A H 0.144084 0.408041 0.572687 0.091 Uiso 1 1 calc R U . . . H2B H 0.175223 0.246474 0.530695 0.091 Uiso 1 1 calc R U . . . C3 C 0.0470(4) 0.2367(7) 0.5141(5) 0.0820(17) Uani 1 1 d . . . . . H3A H 0.014138 0.267198 0.556902 0.098 Uiso 1 1 calc R U . . . H3B H 0.044853 0.114712 0.507644 0.098 Uiso 1 1 calc R U . . . C4 C 0.2981(4) 0.2295(6) 0.8306(4) 0.0712(14) Uani 1 1 d . . . . . H4A H 0.297410 0.108168 0.839281 0.085 Uiso 1 1 calc R U . . . H4B H 0.261604 0.280287 0.864074 0.085 Uiso 1 1 calc R U . . . C5 C 0.3895(3) 0.2920(6) 0.8785(4) 0.0664(14) Uani 1 1 d . . . . . H5A H 0.410185 0.277669 0.953086 0.080 Uiso 1 1 calc R U . . . H5B H 0.390423 0.411650 0.864342 0.080 Uiso 1 1 calc R U . . . C6 C 0.4508(3) 0.2028(5) 0.8398(4) 0.0614(13) Uani 1 1 d . . . . . H6A H 0.441728 0.082180 0.842666 0.074 Uiso 1 1 calc R U . . . H6B H 0.435916 0.232988 0.767728 0.074 Uiso 1 1 calc R U . . . C7 C -0.0004(4) 0.3094(6) 0.4092(4) 0.0717(14) Uani 1 1 d . . . . . C8 C 0.0427(4) 0.4027(7) 0.3602(4) 0.0788(15) Uani 1 1 d . . . . . H8 H 0.103475 0.424500 0.392914 0.095 Uiso 1 1 calc R U . . . C9 C -0.0032(4) 0.4634(7) 0.2639(4) 0.0861(17) Uani 1 1 d . . . . . H9 H 0.025389 0.527013 0.229596 0.103 Uiso 1 1 calc R U . . . C10 C -0.0904(4) 0.4305(7) 0.2188(5) 0.0828(16) Uani 1 1 d . . . . . C11 C -0.1353(4) 0.3413(7) 0.2645(5) 0.0833(16) Uani 1 1 d . . . . . H11 H -0.196271 0.321816 0.231973 0.100 Uiso 1 1 calc R U . . . C12 C -0.0879(4) 0.2809(7) 0.3603(5) 0.0777(16) Uani 1 1 d . . . . . H12 H -0.117215 0.216821 0.393614 0.093 Uiso 1 1 calc R U . . . C13 C 0.6022(4) 0.1141(6) 0.8807(4) 0.0728(15) Uani 1 1 d . . . . . H13A H 0.591736 0.109657 0.807471 0.087 Uiso 1 1 calc R U . . . H13B H 0.588080 0.004183 0.901013 0.087 Uiso 1 1 calc R U . . . C14 C 0.6971(4) 0.1521(9) 0.9404(5) 0.098(2) Uani 1 1 d . . . . . H14A H 0.733835 0.069790 0.923542 0.117 Uiso 1 1 calc R U . . . H14B H 0.709226 0.142960 1.013861 0.117 Uiso 1 1 calc R U . . . C15 C 0.7212(4) 0.3249(9) 0.9174(5) 0.097(2) Uani 1 1 d . . . . . H15A H 0.782512 0.349411 0.961690 0.116 Uiso 1 1 calc R U . . . H15B H 0.716182 0.330496 0.845897 0.116 Uiso 1 1 calc R U . . . C16 C 0.6619(4) 0.4501(7) 0.9350(4) 0.0807(16) Uani 1 1 d . . . . . H16A H 0.675614 0.560940 0.915405 0.097 Uiso 1 1 calc R U . . . H16B H 0.672107 0.453070 1.008187 0.097 Uiso 1 1 calc R U . . . C17 C 0.5677(3) 0.4104(5) 0.8747(4) 0.0629(13) Uani 1 1 d . . . . . H17A H 0.530361 0.492845 0.890337 0.075 Uiso 1 1 calc R U . . . H17B H 0.556377 0.418394 0.801387 0.075 Uiso 1 1 calc R U . . . Cl2 Cl 0.58398(9) 0.23372(11) 1.12766(8) 0.0654(5) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.089(3) 0.0462(19) 0.050(2) 0.0030(15) 0.038(2) 0.0086(18) C1 0.080(4) 0.073(3) 0.072(4) -0.002(3) 0.034(3) -0.009(3) F1 0.120(3) 0.117(3) 0.077(2) 0.009(2) 0.028(2) -0.004(2) O1 0.088(3) 0.071(2) 0.059(2) -0.0010(16) 0.0348(19) -0.0065(17) C2 0.097(4) 0.057(3) 0.077(4) -0.005(2) 0.039(3) -0.009(3) C3 0.095(4) 0.078(4) 0.080(4) -0.001(3) 0.041(3) -0.014(3) C4 0.093(4) 0.071(3) 0.061(3) -0.001(2) 0.042(3) -0.005(3) C5 0.095(4) 0.057(3) 0.058(3) -0.003(2) 0.041(3) 0.003(2) C6 0.094(4) 0.045(2) 0.055(3) -0.002(2) 0.040(3) -0.001(2) C7 0.089(4) 0.065(3) 0.067(3) 0.000(3) 0.036(3) -0.002(3) C8 0.087(4) 0.076(3) 0.078(4) 0.004(3) 0.037(3) -0.007(3) C9 0.093(5) 0.093(4) 0.075(4) 0.013(3) 0.034(4) -0.008(3) C10 0.101(5) 0.076(3) 0.075(4) 0.000(3) 0.036(4) 0.003(3) C11 0.085(4) 0.078(4) 0.092(5) -0.011(3) 0.039(4) -0.007(3) C12 0.082(4) 0.075(3) 0.086(4) -0.005(3) 0.043(4) -0.006(3) C13 0.111(5) 0.063(3) 0.056(3) 0.000(2) 0.044(3) 0.024(3) C14 0.107(5) 0.121(5) 0.067(4) -0.007(4) 0.036(4) 0.044(4) C15 0.090(4) 0.139(6) 0.074(4) -0.028(4) 0.043(3) 0.004(4) C16 0.098(4) 0.089(4) 0.068(3) -0.019(3) 0.046(3) -0.012(3) C17 0.094(4) 0.051(2) 0.055(3) -0.001(2) 0.041(3) -0.004(2) Cl2 0.1296(12) 0.0391(6) 0.0418(7) 0.0037(4) 0.0486(7) 0.0048(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0067 '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' Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0389 0.0241 '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 C6 N1 H1 107.4 . . C6 N1 C13 111.7(4) . . C6 N1 C17 112.0(4) . . C13 N1 H1 107.4 . . C13 N1 C17 110.7(4) . . C17 N1 H1 107.4 . . H1A C1 H1B 108.2 . . O1 C1 H1A 109.7 . . O1 C1 H1B 109.7 . . O1 C1 C2 109.9(4) . . C2 C1 H1A 109.7 . . C2 C1 H1B 109.7 . . C1 O1 C4 113.0(4) . . C1 C2 H2A 109.3 . . C1 C2 H2B 109.3 . . H2A C2 H2B 107.9 . . C3 C2 C1 111.8(4) . . C3 C2 H2A 109.3 . . C3 C2 H2B 109.3 . . C2 C3 H3A 108.0 . . C2 C3 H3B 108.0 . . C2 C3 C7 117.3(5) . . H3A C3 H3B 107.2 . . C7 C3 H3A 108.0 . . C7 C3 H3B 108.0 . . O1 C4 H4A 109.7 . . O1 C4 H4B 109.7 . . O1 C4 C5 109.8(4) . . H4A C4 H4B 108.2 . . C5 C4 H4A 109.7 . . C5 C4 H4B 109.7 . . C4 C5 H5A 109.2 . . C4 C5 H5B 109.2 . . C4 C5 C6 112.0(4) . . H5A C5 H5B 107.9 . . C6 C5 H5A 109.2 . . C6 C5 H5B 109.2 . . N1 C6 C5 113.5(4) . . N1 C6 H6A 108.9 . . N1 C6 H6B 108.9 . . C5 C6 H6A 108.9 . . C5 C6 H6B 108.9 . . H6A C6 H6B 107.7 . . C8 C7 C3 122.0(5) . . C12 C7 C3 119.2(5) . . C12 C7 C8 118.8(5) . . C7 C8 H8 120.2 . . C9 C8 C7 119.6(6) . . C9 C8 H8 120.2 . . C8 C9 H9 120.5 . . C10 C9 C8 118.9(6) . . C10 C9 H9 120.5 . . F1 C10 C9 118.3(5) . . F1 C10 C11 118.4(6) . . C9 C10 C11 123.3(6) . . C10 C11 H11 121.6 . . C10 C11 C12 116.8(6) . . C12 C11 H11 121.6 . . C7 C12 C11 122.6(6) . . C7 C12 H12 118.7 . . C11 C12 H12 118.7 . . N1 C13 H13A 109.3 . . N1 C13 H13B 109.3 . . N1 C13 C14 111.7(4) . . H13A C13 H13B 107.9 . . C14 C13 H13A 109.3 . . C14 C13 H13B 109.3 . . C13 C14 H14A 109.3 . . C13 C14 H14B 109.3 . . C13 C14 C15 111.6(5) . . H14A C14 H14B 108.0 . . C15 C14 H14A 109.3 . . C15 C14 H14B 109.3 . . C14 C15 H15A 109.6 . . C14 C15 H15B 109.6 . . H15A C15 H15B 108.1 . . C16 C15 C14 110.1(5) . . C16 C15 H15A 109.6 . . C16 C15 H15B 109.6 . . C15 C16 H16A 109.4 . . C15 C16 H16B 109.4 . . C15 C16 C17 111.3(5) . . H16A C16 H16B 108.0 . . C17 C16 H16A 109.4 . . C17 C16 H16B 109.4 . . N1 C17 C16 112.0(4) . . N1 C17 H17A 109.2 . . N1 C17 H17B 109.2 . . C16 C17 H17A 109.2 . . C16 C17 H17B 109.2 . . H17A C17 H17B 107.9 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1 H1 1.0000 . N1 C6 1.477(6) . N1 C13 1.489(5) . N1 C17 1.499(5) . C1 H1A 0.9900 . C1 H1B 0.9900 . C1 O1 1.403(6) . C1 C2 1.518(8) . F1 C10 1.362(6) . O1 C4 1.415(6) . C2 H2A 0.9900 . C2 H2B 0.9900 . C2 C3 1.492(8) . C3 H3A 0.9900 . C3 H3B 0.9900 . C3 C7 1.517(8) . C4 H4A 0.9900 . C4 H4B 0.9900 . C4 C5 1.491(7) . C5 H5A 0.9900 . C5 H5B 0.9900 . C5 C6 1.509(6) . C6 H6A 0.9900 . C6 H6B 0.9900 . C7 C8 1.394(7) . C7 C12 1.367(8) . C8 H8 0.9500 . C8 C9 1.381(7) . C9 H9 0.9500 . C9 C10 1.364(8) . C10 C11 1.365(8) . C11 H11 0.9500 . C11 C12 1.378(8) . C12 H12 0.9500 . C13 H13A 0.9900 . C13 H13B 0.9900 . C13 C14 1.506(8) . C14 H14A 0.9900 . C14 H14B 0.9900 . C14 C15 1.522(9) . C15 H15A 0.9900 . C15 H15B 0.9900 . C15 C16 1.496(8) . C16 H16A 0.9900 . C16 H16B 0.9900 . C16 C17 1.501(7) . C17 H17A 0.9900 . C17 H17B 0.9900 . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N1 H1 Cl2 1.00 2.08 3.082(4) 175.6 . yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 N1 C13 C14 C15 -55.2(6) . . . . C1 O1 C4 C5 -179.5(4) . . . . C1 C2 C3 C7 175.5(5) . . . . F1 C10 C11 C12 -179.5(5) . . . . O1 C1 C2 C3 -178.0(4) . . . . O1 C4 C5 C6 -66.7(5) . . . . C2 C1 O1 C4 170.8(4) . . . . C2 C3 C7 C8 7.5(8) . . . . C2 C3 C7 C12 -173.6(5) . . . . C3 C7 C8 C9 178.7(5) . . . . C3 C7 C12 C11 -179.3(5) . . . . C4 C5 C6 N1 -170.1(4) . . . . C6 N1 C13 C14 -179.6(4) . . . . C6 N1 C17 C16 179.0(4) . . . . C7 C8 C9 C10 0.1(9) . . . . C8 C7 C12 C11 -0.3(8) . . . . C8 C9 C10 F1 179.0(5) . . . . C8 C9 C10 C11 0.7(9) . . . . C9 C10 C11 C12 -1.2(9) . . . . C10 C11 C12 C7 1.0(8) . . . . C12 C7 C8 C9 -0.3(8) . . . . C13 N1 C6 C5 161.5(4) . . . . C13 N1 C17 C16 -55.7(5) . . . . C13 C14 C15 C16 54.8(6) . . . . C14 C15 C16 C17 -55.2(6) . . . . C15 C16 C17 N1 56.5(6) . . . . C17 N1 C6 C5 -73.7(5) . . . . C17 N1 C13 C14 54.9(6) . . . . _cod_database_fobs_code 4519487