Enantioselective isoquinuclidine synthesis via sequential Diels–Alder/visible-light photoredox C–C bond cleavage: a formal synthesis of the indole alkaloid catharanthine
Kim, Simon J.; Batey, Robert A.; Organic Chemistry Frontiers 5 (2018) 2934–; doi:10.1039/C8QO00849C

data_1554426
_publ_section_title
;
 Enantioselective isoquinuclidine synthesis via sequential
 Diels--Alder/visible-light photoredox C--C bond cleavage: a formal
 synthesis of the indole alkaloid catharanthine
;
_journal_issue                   20
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2934
_journal_paper_doi               10.1039/C8QO00849C
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H13 N O3'
_chemical_formula_sum            'C14 H13 N O3'
_chemical_formula_weight         243.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-08-09 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.801(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0137(6)
_cell_length_b                   10.3706(6)
_cell_length_c                   11.9870(7)
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.90
_cell_measurement_theta_min      3.92
_cell_volume                     1171.23(12)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17855
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.219
_diffrn_reflns_theta_max         67.218
_diffrn_reflns_theta_min         3.919
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
; 
 Flack x determined using 1877 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4105
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0276
_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^)+(0.0332P)^2^+0.1714P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0697
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                4066
_reflns_number_total             4105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00849c2.cif
_cod_data_source_block           d16137_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1554426
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.818
_shelx_estimated_absorpt_t_max   0.931
_shelx_res_checksum              57521
_shelx_hkl_checksum              55549