Diastereo- and enantioselective construction of biologically important pyrrolo[1,2-a]indole scaffolds via catalytic asymmetric [3 + 2] cyclodimerizations of 3-alkyl-2-vinylindoles
Zhu, Zi-Qi; Yin, Lei; Wang, Yang; Shen, Yang; Li, Can; Mei, Guang-Jian; Shi, Feng; Organic Chemistry Frontiers 4 (2017) 57–; doi:10.1039/C6QO00446F

data_1553519
_publ_section_title
;
 Diastereo- and enantioselective construction of biologically important
 pyrrolo[1,2-a]indole scaffolds via catalytic asymmetric [3 + 2]
 cyclodimerizations of 3-alkyl-2-vinylindoles
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              57
_journal_paper_doi               10.1039/C6QO00446F
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C36 H32 F2 N2 O2'
_chemical_formula_sum            'C36 H32 F2 N2 O2'
_chemical_formula_weight         562.63
_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
_audit_creation_date             2016-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5221)
;
_audit_update_record
;
2016-10-04 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5593(3)
_cell_length_b                   14.0068(3)
_cell_length_c                   17.8914(4)
_cell_measurement_reflns_used    4634
_cell_measurement_temperature    130
_cell_measurement_theta_max      65.12
_cell_measurement_theta_min      3.82
_cell_volume                     2896.78(12)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      130
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16825
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        65.664
_diffrn_reflns_theta_max         65.664
_diffrn_reflns_theta_min         4.008
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.6319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1410 before and 0.0680 after correction.
The Ratio of minimum to maximum transmission is 0.8395.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1787 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.821
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         4925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.821
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0361
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1084
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                4484
_reflns_number_total             4925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00446f3.cif
_cod_data_source_block           cu_dm16560_0m
_cod_original_cell_volume        2896.77(12)
_cod_database_code               1553519
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.919
_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.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C22(H22A,H22B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16), C17(H17), C18(H18),
 C19(H19), C26(H26), C27(H27), C29(H29), C30(H30), C32(H32), C33(H33), C35(H35),
  C36(H36)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C23(H23A,H23B,H23C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'