Diastereo- and Enantioselective Construction of Dihydrobenzo[ e]indole Scaffolds via Catalytic Asymmetric [3 + 2] Cycloannulations.
Li, Can; Xu, Dan-Ni; Ma, Chun; Mei, Guang-Jian; Shi, Feng; The Journal of organic chemistry 83 (2018) 9190–9200; doi:10.1021/acs.joc.8b01217

data_4035296
_publ_section_title
;
 Diastereo- and Enantioselective Construction of Dihydrobenzo[ e]indole
 Scaffolds via Catalytic Asymmetric [3 + 2] Cycloannulations.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9190
_journal_page_last               9200
_journal_paper_doi               10.1021/acs.joc.8b01217
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C30 H27 N3 O2'
_chemical_formula_sum            'C30 H27 N3 O2'
_chemical_formula_weight         461.54
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.0800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.4544(2)
_cell_length_b                   9.3869(2)
_cell_length_c                   12.7713(3)
_cell_measurement_reflns_used    6911
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      59.716
_cell_measurement_theta_min      3.708
_cell_volume                     1243.72(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      301.72
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15748
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.650
_diffrn_reflns_theta_min         3.707
_exptl_absorpt_coefficient_mu    0.397
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1481 before and 0.0625 after correction. The Ratio of minimum to maximum transmission is 0.8175. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1925 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(17)
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5520
_refine_ls_number_restraints     77
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+0.2890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1128
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                4886
_reflns_number_total             5520
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01217_si_002.cif
_cod_data_source_block           mjr17066_0m
_cod_database_code               4035296
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.943
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C29'-C30' = C29'-C28' = C29-C28 = C29-C30
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O2 \\sim C28 \\sim C29 \\sim C30 \\sim C28' \\sim C29' \\sim C30': within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: C28(0.5) H28A(0.5) H28B(0.5) C29(0.5) H29A(0.5) H29B(0.5) C30(0.5)
 H30A(0.5) H30B(0.5) H30C(0.5) C28'(0.5) H28C(0.5) H28D(0.5) C29'(0.5)
 H29C(0.5) H29D(0.5) C30'(0.5) H30D(0.5) H30E(0.5) H30F(0.5)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2A)
5.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C29(H29A,H29B), C28'(H28C,H28D), C29'(H29C,H29D)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26)
5.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C30'(H30D,H30E,H30F)
;
_shelx_res_checksum              21628
_shelx_hkl_checksum              18060
_olex2_submission_special_instructions 'No special instructions were received'