Rh(II)-catalyzed cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines: switchable reactivity of Rh-azavinylcarbene as [2C]- or aza-[3C]-synthon
Yuanhao Wang; Xiaoqiang Lei; Yefeng Tang; Chem.Commun. 51 (2015) 4507–; doi:10.1039/C5cc00268K

data_7116650
_publ_section_title
;
 Rh(II)-catalyzed cycloadditions of 1-tosyl 1,2,3-triazoles with
 2H-azirines: switchable reactivity of Rh-azavinylcarbene as [2C]- or
 aza-[3C]-synthon
;
_journal_name_full               Chem.Commun.
_journal_page_first              4507
_journal_paper_doi               10.1039/C5cc00268K
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C30 H23 Br N2 O3 S'
_chemical_formula_sum            'C30 H23 Br N2 O3 S'
_chemical_formula_weight         571.47
_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_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-07-04
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2014-11-04 deposited with the CCDC.
2015-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.857(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2526(8)
_cell_length_b                   8.7689(4)
_cell_length_c                   19.1451(11)
_cell_measurement_reflns_used    3171
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      28.3200
_cell_measurement_theta_min      3.9150
_cell_volume                     2560.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9903
_diffrn_measured_fraction_theta_max 0.8364
_diffrn_measurement_details
;
  1 omega  -87.00   -4.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.5610  -38.0000  -90.0000 83

  2 omega  -80.00   11.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.5610  -57.0000 -180.0000 91
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0110125000
_diffrn_orient_matrix_UB_12      0.0000975000
_diffrn_orient_matrix_UB_13      0.0361370000
_diffrn_orient_matrix_UB_21      -0.0451496000
_diffrn_orient_matrix_UB_22      -0.0031772000
_diffrn_orient_matrix_UB_23      0.0082507000
_diffrn_orient_matrix_UB_31      0.0017630000
_diffrn_orient_matrix_UB_32      -0.0807961000
_diffrn_orient_matrix_UB_33      -0.0002772000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10317
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.441
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.723
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.722
_refine_diff_density_min         -0.883
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         5004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0332P)^2^+3.3467P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1125
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3632
_reflns_number_total             5004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc00268k2.cif
_cod_data_source_block           exp_3783
_cod_database_code               7116650
_chemical_oxdiff_formula         'C1 N1'
_reflns_odcompleteness_completeness 99.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25),
  C26(H26), C28(H28), C29(H29)
2.b Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.724
_shelxl_version_number           2013-3