Enantioselective total synthesis of (+)-arborescidine C and related tetracyclic indole alkaloids using organocatalysis.
Sheth, Vishal M.; Hong, Bor-Cherng; Lee, Gene-Hsiang; Organic & biomolecular chemistry 15 (2017) 3408–3412; doi:10.1039/c7ob00473g

data_7155613
_publ_section_title
;
 Enantioselective total synthesis of (+)-arborescidine C and related
 tetracyclic indole alkaloids using organocatalysis.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3408
_journal_page_last               3412
_journal_paper_doi               10.1039/c7ob00473g
_journal_volume                  15
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H20 N2 O3'
_chemical_formula_weight         300.35
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-21 deposited with the CCDC.
2017-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.86390(10)
_cell_length_b                   8.5853(2)
_cell_length_c                   29.2551(6)
_cell_measurement_reflns_used    9116
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      70.21
_cell_measurement_theta_min      3.02
_cell_volume                     1472.80(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9796
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.983
_diffrn_reflns_theta_min         3.021
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
; 
 Flack x determined using 1106 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.253
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2801
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.427
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+0.3043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2743
_reflns_number_total             2801
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00473g2.cif
_cod_data_source_block           ic17656
_cod_database_code               7155613
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.821
_shelx_estimated_absorpt_t_max   0.970
_shelx_res_checksum              47389