Multiple Hydrogen-Bonding Bifunctional Thiourea-Catalyzed Asymmetric Dearomative [4 + 2] Annulation of 3-Nitroindoles: Highly Enantioselective Access to Hydrocarbazole Skeletons.
Yue, Deng-Feng; Zhao, Jian-Qiang; Chen, Xiao-Zhen; Zhou, Yan; Zhang, Xiao-Mei; Xu, Xiao-Ying; Yuan, Wei-Cheng; Organic letters 19 (2017) 4508–4511; doi:10.1021/acs.orglett.7b02068

data_1547005
_publ_section_title
;
 Multiple Hydrogen-Bonding Bifunctional Thiourea-Catalyzed Asymmetric
 Dearomative [4 + 2] Annulation of 3-Nitroindoles: Highly Enantioselective
 Access to Hydrocarbazole Skeletons.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4508
_journal_page_last               4511
_journal_paper_doi               10.1021/acs.orglett.7b02068
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H28 N2 O8 S'
_chemical_formula_sum            'C30 H28 N2 O8 S'
_chemical_formula_weight         576.60
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.0830(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9714(9)
_cell_length_b                   16.4516(14)
_cell_length_c                   15.5080(13)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.78
_cell_measurement_theta_min      2.24
_cell_volume                     2777.8(4)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.921
_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  0.0188
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            31091
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.062
_diffrn_reflns_theta_min         1.323
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       block
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.400
_exptl_transmission_factor_max   0.7462
_exptl_transmission_factor_min   0.7058
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 6782 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     745
_refine_ls_number_reflns         15831
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.054
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0492P)^2^+0.3772P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0824
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.856
_reflns_number_gt                15108
_reflns_number_total             15831
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02068_si_002.cif
_cod_data_source_block           mo_wlx_ydf2_0m
_cod_database_code               1547005
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.925
_shelx_estimated_absorpt_t_max   0.934
_shelx_res_checksum              24581
_shelx_hkl_checksum              85283