Diastereoselective Synthesis of (±)-<i>epi</i>-Subincanadine C.
Kalshetti, Manojkumar G.; Argade, Narshinha P.; ACS omega 3 (2018) 5308–5316; doi:10.1021/acsomega.8b00587

data_4515969
_publ_section_title
;
 Diastereoselective Synthesis of (+-)-<i>epi</i>-Subincanadine C.
;
_journal_issue                   5
_journal_name_full               'ACS omega'
_journal_page_first              5308
_journal_page_last               5316
_journal_paper_doi               10.1021/acsomega.8b00587
_journal_volume                  3
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H28 N2 O3'
_chemical_formula_sum            'C22 H28 N2 O3'
_chemical_formula_weight         368.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1549(7)
_cell_length_b                   14.3911(12)
_cell_length_c                   16.5026(12)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.79
_cell_volume                     1936.7(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1119
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            47710
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.359
_diffrn_reflns_theta_min         2.468
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.984
_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    1.264
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1316 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(6)
_refine_ls_extinction_coef       0.0156(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0370P)^2^+0.5940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3591
_reflns_number_total             4832
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b00587_si_003.cif
_cod_data_source_block           KAP_02_a
_cod_database_code               4515969
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              38689
_shelx_hkl_checksum              42493