Silver catalysed asymmetric [3+2] cycloaddition for the construction of 5−5-membered 1,3'-indolyl pyrrole atropisomers
Deng, Zhengguo; Xie, Yan; Xiong, Chao; Lv, Jiayang; Chen, Xinyu; Yao, Jinzhong; Zhong, Weihui; Ling, Fei; Chemical Communications  (2026) –; doi:10.1039/D6CC00517A

data_7135680
_publ_section_title
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 Silver-catalysed asymmetric [3+2] cycloaddition for the construction of
 5-5-membered 1,3'-indolyl pyrrole atropisomers.
;
_journal_issue                   33
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8471
_journal_page_last               8475
_journal_paper_doi               10.1039/d6cc00517a
_journal_volume                  62
_journal_year                    2026
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H28 N2 O4'
_chemical_formula_sum            'C31 H28 N2 O4'
_chemical_formula_weight         492.55
_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             2025-09-24
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-01-26 deposited with the CCDC.	2026-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7730(4)
_cell_length_b                   13.0922(5)
_cell_length_c                   16.6122(6)
_cell_measurement_reflns_used    9385
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.602
_cell_measurement_theta_min      4.004
_cell_volume                     2560.51(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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      170.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III M28'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON III'
_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           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            55344
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.693
_diffrn_reflns_theta_min         4.004
_diffrn_source                   'liquid Metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.24954300000000001
_diffrn_source_type              'Bruker Excillum Metaljet D2+'
_diffrn_source_voltage           69.9
_exptl_absorpt_coefficient_mu    0.452
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1679 before and 0.1002 after correction.
The Ratio of minimum to maximum transmission is 0.9050.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 2388 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0463P)^2^+0.4682P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                5654
_reflns_number_total             5857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00517a2.cif
_cod_data_source_block           250923_dzg_4ome_s_l
_cod_depositor_comments          'Adding full bibliography for 7135680.cif.'
_cod_database_code               7135680
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.854
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C8(H8), C10(H10), C11(H11), C12(H12),
  C13(H13), C14(H14), C17(H17), C26(H26), C27(H27), C29(H29), C30(H30)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C31(H31A,H31B,
 H31C)
;
_shelx_res_checksum              82493
_shelx_hkl_checksum              614
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_olex2_submission_special_instructions 'No special instructions were received'