Enantioselective synthesis of polycyclic pyrrole derivatives by iridium-catalyzed asymmetric allylic dearomatization and ring-expansive migration reactions.
Huang, Lin; Xie, Jia-Hao; Cai, Yue; Zheng, Chao; Hou, Xue-Long; Dai, Li-Xin; You, Shu-Li; Chemical communications (Cambridge, England) 57 (2021) 5390–5393; doi:10.1039/d1cc01929e

data_7128249
_publ_section_title
;
 Enantioselective synthesis of polycyclic pyrrole derivatives by
 iridium-catalyzed asymmetric allylic dearomatization and ring-expansive
 migration reactions.
;
_journal_issue                   44
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5390
_journal_page_last               5393
_journal_paper_doi               10.1039/d1cc01929e
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H22 N2 O2 S'
_chemical_formula_sum            'C22 H22 N2 O2 S'
_chemical_formula_weight         378.47
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2020-12-07 deposited with the CCDC.	2021-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                71.155(2)
_cell_angle_beta                 70.007(2)
_cell_angle_gamma                61.631(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4904(7)
_cell_length_b                   9.8661(7)
_cell_length_c                   12.9696(9)
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      30.317
_cell_measurement_theta_min      2.392
_cell_volume                     985.04(12)
_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      300.88
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_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  0.0546
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24092
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.504
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1232 before and 0.0760 after correction. The Ratio of minimum to maximum transmission is 0.9105. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.418
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 2736 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_coef       0.21(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         7641
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0764
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1501P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1843
_refine_ls_wR_factor_ref         0.2003
_reflns_Friedel_coverage         0.983
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                6576
_reflns_number_total             7641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01929e2.cif
_cod_data_source_block           mo_d8v17087_0m
_cod_depositor_comments          'Adding full bibliography for 7128249.cif.'
_cod_database_code               7128249
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.942
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C23(H23A,H23B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C20(H20), C21(H21), C27(H27), C29(H29), C30(H30), C33(H33),
  C34(H34), C35(H35), C36(H36), C37(H37), C39(H39), C40(H40), C42(H42), C43(H43)
2.d X=CH2 refined with riding coordinates:
 C6(H6A,H6B), C28(H28A,H28B)
2.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C44(H44A,H44B,H44C)
;
_shelx_res_checksum              27190
_olex2_submission_special_instructions 'No special instructions were received'