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_7124376
_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         'C19 H21 N2 O2, C18 H23 N2'
_chemical_formula_sum            'C37 H44 N4 O2'
_chemical_formula_weight         576.76
_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   mixed
_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                 97.3341(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.9559(3)
_cell_length_b                   33.9149(10)
_cell_length_c                   20.7715(6)
_cell_measurement_reflns_used    9806
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.1090
_cell_measurement_theta_min      4.4609
_cell_volume                     6257.5(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_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 7.4074
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type
;
Bruker AXS D8 Quest CMOS diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35000
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.175
_diffrn_reflns_theta_min         2.509
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6575
_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    1.224
_exptl_crystal_description       fragment
_exptl_crystal_F_000             2480
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     791
_refine_ls_number_reflns         11830
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+2.0300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1092
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10748
_reflns_number_total             11830
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06429j2.cif
_cod_data_source_block           DespiramineCarbamate
_cod_database_code               7124376
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.885
_shelx_estimated_absorpt_t_max   0.916
_shelx_res_checksum              76897