Common Strategy for the Synthesis of Some Strychnos Indole Alkaloids.
Maertens, Gaetan; Deruer, Elsa; Denis, Maxime; Canesi, Sylvain; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00572

data_4038254
_publ_section_title
;
 Common Strategy for the Synthesis of Some Strychnos Indole Alkaloids.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00572
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C19 H19 N O4'
_chemical_formula_sum            'C19 H19 N O4'
_chemical_formula_weight         325.35
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_symmetry_cell_setting           trigonal
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc1ktw3c
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-02-19 deposited with the CCDC.	2020-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   8.6520(2)
_cell_length_b                   8.6520(2)
_cell_length_c                   19.0082(6)
_cell_measurement_reflns_used    6230
_cell_measurement_temperature    149(2)
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      5.91
_cell_volume                     1232.27(6)
_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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      149(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18370
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.271
_diffrn_reflns_theta_min         5.905
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  0.7360
_exptl_absorpt_correction_T_min  0.6560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/2 - Bruker AXS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       needle
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.155
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
; 
 Flack x determined using 1376 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.16(12)
_refine_ls_extinction_coef       0.0082(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3007
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0397P)^2^+0.0724P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0807
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2906
_reflns_number_total             3007
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00572_si_002.cif
_cod_data_source_block           cu_Gaetan1_0m
_cod_original_cell_volume        1232.27(7)
_cod_database_code               4038254
_shelx_estimated_absorpt_t_min   0.773
_shelx_estimated_absorpt_t_max   0.892
_shelxl_version_number           2014-3
_shelx_res_checksum              7509
_shelx_hkl_checksum              52195