Efficient construction of functionalized pyrroloindolines through cascade radical cyclization/intermolecular coupling.
Jiang, Yonggang; Liu, Dongxiang; Zhang, Lening; Qin, Cuirong; Li, Hui; Yang, Haitao; Walsh, Patrick J.; Yang, Xiaodong; Chemical science 15 (2024) 2205–2210; doi:10.1039/d3sc05210a

data_1570698
_publ_section_title
;
 Efficient construction of functionalized pyrroloindolines through cascade
 radical cyclization/intermolecular coupling.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              2205
_journal_page_last               2210
_journal_paper_doi               10.1039/d3sc05210a
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C32 H27 F2 N3 O'
_chemical_formula_sum            'C32 H27 F2 N3 O'
_chemical_formula_weight         507.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-09-05
_audit_creation_method
;
FinalCif V88 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_audit_update_record
;
2023-09-07 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.468(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9152(16)
_cell_length_b                   9.8681(9)
_cell_length_c                   18.7455(19)
_cell_measurement_reflns_used    6070
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.16
_cell_measurement_theta_min      2.33
_cell_volume                     2567.6(5)
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0740
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16313
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.386
_diffrn_reflns_theta_min         2.335
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1031 before and 0.0787 after correction.
The Ratio of minimum to maximum transmission is 0.7215.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1753 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5799
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0525P)^2^+0.0218P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1184
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.913
_reflns_Friedel_fraction_max     0.812
_reflns_number_gt                4877
_reflns_number_total             5799
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05210a2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1570698--1570699.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1570698
_shelx_shelxl_version_number     2018/3
_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:
 C8(H8), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C32(H32), C2(H2), C28(H28), C19(H19), C17(H17), C29(H29), C22(H22), C15(H15),
 C31(H31), C24(H24), C26(H26), C30(H30), C25(H25), C5(H5), C4(H4), C23(H23),
 C3(H3)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.986
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_shelx_res_checksum              57496
_shelx_hkl_checksum              53693