Enantioselective Synthesis of Dihydropyridines Containing Quaternary Stereocenters Through Dearomatization of Pyridinium Salts
Robinson, Donovan J.; Spurlin, Sean P.; Gorden, John D.; Karimov, Rashad R.; ACS Catalysis  (2019) 51–; doi:10.1021/acscatal.9b03874

data_4517147
_publ_section_title
;
 Enantioselective Synthesis of Dihydropyridines Containing Quaternary
 Stereocenters Through Dearomatization of Pyridinium Salts
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              51
_journal_paper_doi               10.1021/acscatal.9b03874
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         C17H18N2O2
_chemical_formula_sum            'C17 H18 N2 O2'
_chemical_formula_weight         282.33
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                69.309(2)
_cell_angle_beta                 86.674(2)
_cell_angle_gamma                77.439(2)
_cell_formula_units_Z            2
_cell_length_a                   6.3260(3)
_cell_length_b                   10.0783(4)
_cell_length_c                   12.7658(5)
_cell_measurement_reflns_used    9843
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      74.4153
_cell_measurement_theta_min      3.7020
_cell_volume                     743.01(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection
'Bruker Instrument Service, BIS, v6.2.6 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  'APEX3 v2018.1-0 (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21268
_diffrn_reflns_theta_full        72.07
_diffrn_reflns_theta_max         72.07
_diffrn_reflns_theta_min         3.70
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS DIAMOND'
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Thin Plate'
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.219
_refine_ls_abs_structure_details
;

Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         5633
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0840P)^2^+0.1201P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1308
_reflns_number_gt                5420
_reflns_number_total             5633
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03874_si_003.cif
_cod_data_source_block           Karimov052919
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
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_cod_database_code               4517147
_shelx_res_checksum              6976
_shelx_hkl_checksum              97736