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_1553520
_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_formula_moiety         'C44 H50 N2'
_chemical_formula_sum            'C44 H50 N2'
_chemical_formula_weight         606.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-06-09 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.306(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.661(13)
_cell_length_b                   10.710(7)
_cell_length_c                   17.118(11)
_cell_measurement_reflns_used    1627
_cell_measurement_temperature    130
_cell_measurement_theta_max      20.719
_cell_measurement_theta_min      2.741
_cell_volume                     3575(4)
_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 0.975
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1111
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6181
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.049
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_min         2.089
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2008/4 (Bruker,2010) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1441 before and 0.0652 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1486 before and 0.0778 after correction.
 The Ratio of minimum to maximum transmission is 0.51.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 51677 reflections, Rint = 0.1701
 (10688 with I > 3sig(I), Rint = 0.1072)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         6181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1483
_refine_ls_R_factor_gt           0.0877
_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^)+(0.0832P)^2^+2.0457P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1849
_refine_ls_wR_factor_ref         0.2210
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3734
_reflns_number_total             6181
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00446f2.cif
_cod_data_source_block           dm16261
_cod_database_code               1553520
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.701(6) 0.299(6)
2. 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
3.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C32(H32A,H32B), C43(H43A,H43B)
3.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17),
 C18(H18), C23(H23), C24(H24), C26(H26), C27(H27), C34(H34), C35(H35), C37(H37),
  C38(H38)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C44(H44A,
 H44B,H44C)
;
_shelx_res_checksum              83332
_shelx_hkl_checksum              62429
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'