Rhodium(ii)-catalyzed divergent intramolecular tandem cyclization of N- or O-tethered cyclohexa-2,5-dienones with 1-sulfonyl-1,2,3-triazole: synthesis of cyclopropa[cd]indole and benzofuran derivatives
Zhu, Cheng-Zhi; Wei, Yin; Shi, Min; Organic Chemistry Frontiers 6 (2019) 2884–; doi:10.1039/C9QO00714H

data_1555030
_publ_section_title
;
 Rhodium(ii)-catalyzed divergent intramolecular tandem cyclization of N-
 or O-tethered cyclohexa-2,5-dienones with 1-sulfonyl-1,2,3-triazole:
 synthesis of cyclopropa[cd]indole and benzofuran derivatives
;
_journal_issue                   16
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2884
_journal_paper_doi               10.1039/C9QO00714H
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C21 H16 Br N O4 S'
_chemical_formula_weight         458.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-04-25 deposited with the CCDC.	2019-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                102.4310(10)
_cell_angle_beta                 97.6580(10)
_cell_angle_gamma                98.7680(10)
_cell_formula_units_Z            2
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_cell_length_b                   10.9804(4)
_cell_length_c                   12.5285(4)
_cell_measurement_reflns_used    9489
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.984
_cell_measurement_theta_min      5.716
_cell_volume                     936.85(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.989
_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  0.0713
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
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_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
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_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16426
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.858
_exptl_absorpt_coefficient_mu    2.334
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.028(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0488P)^2^+0.5742P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3264
_reflns_number_total             3647
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00714h1.cif
_cod_data_source_block           mo_d8v18343_0m
_cod_database_code               1555030
_shelx_estimated_absorpt_t_min   0.679
_shelx_estimated_absorpt_t_max   0.767
_shelxl_version_number           2013-4
_shelx_res_checksum              25663
_shelx_hkl_checksum              36867