Rhodium(ii)-catalyzed intermolecular [3 + 2] annulation of N-vinyl indoles with N-tosyl-1,2,3-triazoles via an aza-vinyl Rh carbene
Jiang, Bo; Shi, Min; Organic Chemistry Frontiers 4 (2017) 2459–; doi:10.1039/C7QO00703E

data_1553876
_publ_section_title
;
 Rhodium(ii)-catalyzed intermolecular [3 + 2] annulation of N-vinyl
 indoles with N-tosyl-1,2,3-triazoles via an aza-vinyl Rh carbene
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2459
_journal_paper_doi               10.1039/C7QO00703E
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C44 H45 Br2 N3 O6 S2'
_chemical_formula_sum            'C44 H45 Br2 N3 O6 S2'
_chemical_formula_weight         935.77
_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     dual
_audit_creation_date             2017-08-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-08-23 deposited with the CCDC.
2017-09-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.559(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.823(2)
_cell_length_b                   11.5473(19)
_cell_length_c                   30.267(5)
_cell_measurement_reflns_used    4075
_cell_measurement_temperature    272(2)
_cell_measurement_theta_max      21.610
_cell_measurement_theta_min      2.23
_cell_volume                     4777.4(13)
_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      272.29
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.1150
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            22460
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         2.698
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.830
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0882 before and 0.0552 after correction. The Ratio of minimum to maximum transmission is 0.7598. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     518
_refine_ls_number_reflns         10781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.1540
_refine_ls_R_factor_gt           0.0663
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1030P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1613
_refine_ls_wR_factor_ref         0.2048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4890
_reflns_number_total             10781
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00703e2.cif
_cod_data_source_block           mo_d8v17274_0m
_cod_original_cell_volume        4777.3(14)
_cod_database_code               1553876
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.771
_shelx_estimated_absorpt_t_min   0.689
_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:
 C1(H1), C4(H4), C5(H5), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C15(H15A,H15B), C36(H36A,H36B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C13(H13), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C31(H31), C32(H32), C33(H33),
  C34(H34), C35(H35), C39(H39), C40(H40), C42(H42), C43(H43)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C29(H29A,H29B,H29C), C37(H37A,H37B,H37C), C44(H44A,H44B,
 H44C)
;
_shelx_res_checksum              80378
_shelx_fab_checksum              26867
_olex2_submission_special_instructions 'No special instructions were received'