Enantioselective Construction of cis-Hydroindole Scaffolds via Asymmetric Inverse-Electron-Demand Diels–Alder Reaction: Application to the Formal Total Synthesis of (+)-Minovincine
Zhang, Fangqing; Ren, Bing-Tao; Zhou, Yuqiao; Liu, Yangbin; Feng, Xiaoming; Chemical Science  (2022) –; doi:10.1039/D2SC01458K

data_1566806
_publ_section_title
;
 Enantioselective Construction of cis-Hydroindole Scaffolds via Asymmetric
 Inverse-Electron-Demand Diels--Alder Reaction: Application to the Formal
 Total Synthesis of (+)-Minovincine
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC01458K
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H19 N O6'
_chemical_formula_sum            'C19 H19 N O6'
_chemical_formula_weight         357.35
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-13 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.76190(10)
_cell_length_b                   9.03950(10)
_cell_length_c                   21.2088(3)
_cell_measurement_reflns_used    8629
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      76.5620
_cell_measurement_theta_min      6.3880
_cell_volume                     1679.80(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9198
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.665
_diffrn_reflns_theta_min         6.434
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.885
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.64a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ether dicloromethane'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1358 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_extinction_coef       0.0133(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3354
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0262
_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^)+(0.0366P)^2^+0.3480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0707
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                3318
_reflns_number_total             3354
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01458k2.cif
_cod_data_source_block           2001105006
_cod_database_code               1566806
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              83244
_shelx_hkl_checksum              80683