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_7116651
_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         'C29 H24 N2 O2 S'
_chemical_formula_sum            'C29 H24 N2 O2 S'
_chemical_formula_weight         464.56
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-09-16
_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                 95.591(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7344(7)
_cell_length_b                   11.3573(6)
_cell_length_c                   15.3726(9)
_cell_measurement_reflns_used    3901
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      28.8540
_cell_measurement_theta_min      3.4330
_cell_volume                     2386.5(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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
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      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9945
_diffrn_measured_fraction_theta_max 0.8562
_diffrn_measurement_details
;
  1 omega  -16.00    9.00   1.0000    1.6500
omega____ theta____ kappa____ phi______ frames
    -      -11.6392   38.0000  -60.0000 25

  2 omega  -20.00    5.00   1.0000    1.6500
omega____ theta____ kappa____ phi______ frames
    -      -11.6392  -99.0000   30.0000 25

  3 omega  -90.00  -28.00   1.0000    1.6500
omega____ theta____ kappa____ phi______ frames
    -      -11.6392  -77.0000  120.0000 62

  4 omega   -6.00   21.00   1.0000    1.6500
omega____ theta____ kappa____ phi______ frames
    -      -11.6392  -77.0000  120.0000 27

  5 omega  -74.00   18.00   1.0000    1.6500
omega____ theta____ kappa____ phi______ frames
    -      -11.6392  -57.0000  150.0000 92
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0509707000
_diffrn_orient_matrix_UB_12      0.0002067000
_diffrn_orient_matrix_UB_13      0.0042127000
_diffrn_orient_matrix_UB_21      0.0096451000
_diffrn_orient_matrix_UB_22      -0.0064692000
_diffrn_orient_matrix_UB_23      0.0459339000
_diffrn_orient_matrix_UB_31      0.0012054000
_diffrn_orient_matrix_UB_32      0.0621004000
_diffrn_orient_matrix_UB_33      0.0047835000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12465
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         2.922
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70282
_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    1.293
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+0.4769P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1150
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3611
_reflns_number_total             4665
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc00268k2.cif
_cod_data_source_block           exp_4057
_cod_database_code               7116651
_chemical_oxdiff_formula         C19H24O2N2S1
_reflns_odcompleteness_completeness 99.45
_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 Ternary CH refined with riding coordinates:
 C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
  C24(H24), C25(H25), C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C29(H29a,H29b,H29c)
;
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.968
_shelxl_version_number           2013-3