Rhodium(II) catalysed highly diastereoselective synthesis of indolyl-pyrrolo[2,1-<i>a</i>]isoindoles from phthalimide-derived <i>N</i>-sulfonyl-1,2,3-triazoles and indoles.
Patil, Shivaji V.; Bhanage, Bhalchandra M.; Verma, Ajay; Dawande, Sudam G.; Organic & biomolecular chemistry 23 (2025) 8437–8441; doi:10.1039/d5ob01295c

data_7160708
_publ_section_title
;
 Rhodium(II) catalysed highly diastereoselective synthesis of
 indolyl-pyrrolo[2,1-<i>a</i>]isoindoles from phthalimide-derived
 <i>N</i>-sulfonyl-1,2,3-triazoles and indoles.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8437
_journal_page_last               8441
_journal_paper_doi               10.1039/d5ob01295c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C26 H21 N3 O4 S'
_chemical_formula_sum            'C26 H21 N3 O4 S'
_chemical_formula_weight         471.540
_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'
_symmetry_Int_Tables_number      14
_audit_block_doi                 10.5517/ccdc.csd.cc2l7w0r
_audit_creation_date             2024-07-19
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-14 deposited with the CCDC.	2025-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.165(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7276(11)
_cell_length_b                   30.773(3)
_cell_length_c                   7.4588(5)
_cell_measurement_reflns_used    1894
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.24
_cell_measurement_theta_min      2.65
_cell_volume                     2649.6(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0913
_diffrn_reflns_Laue_measured_fraction_full 0.9994
_diffrn_reflns_Laue_measured_fraction_max 0.9994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17560
_diffrn_reflns_point_group_measured_fraction_full 0.9994
_diffrn_reflns_point_group_measured_fraction_max 0.9994
_diffrn_reflns_theta_full        24.9990
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.76
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6453
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0719 before and 0.0590 after correction.
The Ratio of minimum to maximum transmission is 0.8658.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             985.121
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.3349
_refine_diff_density_min         -0.3874
_refine_diff_density_rms         0.0781
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             11.5435
_refine_ls_extinction_coef       0.0012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   0.8996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    37
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.8996
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0600P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1278
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              36
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                2641
_reflns_number_total             4650
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob01295c2.cif
_cod_data_source_block           p01
_cod_depositor_comments
'Adding full bibliography for 7160708--7160709.cif.'
_cod_original_formula_sum        'C26 H21 N3 O4 S1'
_cod_database_code               7160708
_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. Uiso/Uaniso restraints and constraints
O3 \\sim O4: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
3.a Ternary CH refined with riding coordinates:
 C20(H20)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18a,H18b)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
3.d Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'