Unorthodox crystalline drug salts via the reaction of amine-containing drugs with CO2
Soltani, Mohammad; Mash, Brandon L.; Henseler, Julian; Badri, Sharhzad; Zeller, Matthias; Salter, E. Alan; Wierzbicki, Andrzej; Stenson, Alexandra C.; Davis, James H.; Chemical Communications  (2019) –; doi:10.1039/C9CC06429J

data_7124375
_publ_section_title
;
 Unorthodox crystalline drug salts via the reaction of amine-containing
 drugs with CO2
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06429J
_journal_year                    2019
_chemical_formula_moiety         'C20 H20 N O2, C19 H22 N'
_chemical_formula_sum            'C39 H42 N2 O2'
_chemical_formula_weight         570.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-08-15 deposited with the CCDC.    2019-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.9021(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8194(6)
_cell_length_b                   27.0609(15)
_cell_length_c                   11.5232(6)
_cell_measurement_reflns_used    9244
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.7551
_cell_measurement_theta_min      2.4291
_cell_volume                     3130.3(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Apex3 v2018.1-0 (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_refinement
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev946 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            89404
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.772
_diffrn_reflns_theta_min         2.526
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       plate
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0070(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         8095
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0353P)^2^+2.4499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7038
_reflns_number_total             8095
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06429j2.cif
_cod_data_source_block           NortryptileneCarbamate
_cod_database_code               7124375
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              40121