Rh(iii)-Catalyzed chemo-, regio- and stereoselective carboamination of sulfonyl allenes with N-phenoxy amides or N-enoxy imides
Wu, Min; Zhang, Haiman; Wang, Ting; Lin, Shuang; Guo, Ziyang; Gao, Hui; Zhou, Zhi; Yi, Wei; Chemical Communications  (2022) –; doi:10.1039/D2CC02982K

data_7130441
_publ_section_title
;
 Rh(iii)-Catalyzed chemo-, regio- and stereoselective carboamination of
 sulfonyl allenes with N-phenoxy amides or N-enoxy imides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02982K
_journal_year                    2022
_chemical_formula_moiety         'C20 H23 N O4 S'
_chemical_formula_sum            'C20 H23 N O4 S'
_chemical_formula_weight         373.45
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-14
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2022-03-31 deposited with the CCDC.	2022-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.211(11)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.1418(19)
_cell_length_b                   11.1056(12)
_cell_length_c                   20.762(2)
_cell_measurement_reflns_used    5247
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      26.7640
_cell_measurement_theta_min      2.6870
_cell_volume                     4413.6(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -63.00 -11.00   1.00    7.00    --   11.90 -77.00 -60.00   52
  2  \w     -2.00  44.00   1.00    7.00    --   11.90 -77.00 -60.00   46
  3  \w     -3.00  53.00   1.00    7.00    --   11.90  57.00  90.00   56
  4  \w     -7.00  20.00   1.00    7.00    --  -11.27 -99.00-180.00   27
  5  \w    -20.00  47.00   1.00    7.00    --   11.90 -99.00   0.00   67
  6  \w      3.00  28.00   1.00    7.00    --   11.90 -99.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0278758000
_diffrn_orient_matrix_UB_12      -0.0076370000
_diffrn_orient_matrix_UB_13      -0.0220630000
_diffrn_orient_matrix_UB_21      0.0243943000
_diffrn_orient_matrix_UB_22      0.0065422000
_diffrn_orient_matrix_UB_23      0.0255783000
_diffrn_orient_matrix_UB_31      -0.0008546000
_diffrn_orient_matrix_UB_32      -0.0630601000
_diffrn_orient_matrix_UB_33      0.0051057000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0947
_diffrn_reflns_av_unetI/netI     0.0922
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25767
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.962
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         7719
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0950
_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^)+(0.1310P)^2^+7.8050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2462
_refine_ls_wR_factor_ref         0.2662
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5511
_reflns_number_total             7719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02982k2.cif
_cod_data_source_block           805-3b
_cod_original_cell_volume        4413.7(8)
_cod_database_code               7130441
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 98.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, All O(H) groups
2. Restrained distances
 N2-H2
 0.87 with sigma of 0.01
 C16-C15
 1.41 with sigma of 0.01
 C16-H16C
 0.8 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3A), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27), C30(H30), C31(H31),
  C32(H32), C33(H33)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C39(H39A,H39B,H39C), C40(H40A,
 H40B,H40C)
3.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O8(H8)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              87839
_shelx_hkl_checksum              56945
_shelx_fab_checksum              46175
_olex2_date_sample_data_collection 2021-07-14
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.856
_oxdiff_exptl_absorpt_empirical_full_min 0.465