Synthesis, structure and catalytic activity of organozinc complexes derived from chiral sulfonylamidoazetidines
Zhao, Hongyan; Zhang, Shaohui; Fang, Xiaojun; Chen, Liang; Ren, Wenshan; Inorganica Chimica Acta 511 (2020) 119767–; doi:10.1016/j.ica.2020.119767

data_1564149
_publ_section_title
;
 Synthesis, structure and catalytic activity of organozinc complexes
 derived from chiral sulfonylamidoazetidines
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119767
_journal_paper_doi               10.1016/j.ica.2020.119767
_journal_volume                  511
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C24 H26 N2 O2 S'
_chemical_formula_sum            'C24 H26 N2 O2 S'
_chemical_formula_weight         406.53
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.54575(8)
_cell_length_b                   13.85892(12)
_cell_length_c                   18.16386(14)
_cell_measurement_reflns_used    7908
_cell_measurement_temperature    149.7(4)
_cell_measurement_theta_max      72.8710
_cell_measurement_theta_min      4.0020
_cell_volume                     2151.23(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_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_environment      N~2~
_diffrn_ambient_temperature      149.7(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_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    -91.00  -3.00   1.00    4.89    --  -37.03 126.00-180.00   88
  2  \w   -104.00 -20.00   1.00    4.89    --  -37.03 -57.00  90.00   84
  3  \w     20.00 104.00   1.00    4.89    --   37.03  57.00 -30.00   84
  4  \w     20.00 104.00   1.00    4.89    --   37.03  57.00  60.00   84
  5  \w     41.00 109.00   1.00   20.00    --  110.47 -95.00-180.00   68
  6  \w     42.00 128.00   1.00   20.00    --  110.47 -45.00   0.00   86
  7  \w     41.00 109.00   1.00   20.00    --  110.47 -95.00  30.00   68
  8  \w     40.00 149.00   1.00   20.00    --  110.47 -15.00-120.00  109
  9  \w    101.00 178.00   1.00   20.00    --  110.47 102.00 -77.00   77
 10  \w    101.00 178.00   1.00   20.00    --  110.47 112.00 120.00   77
 11  \w   -106.00 -18.00   1.00    4.89    --  -37.03 -38.00-180.00   88
 12  \w      1.00  42.00   1.00    4.89    --   37.03 -99.00  60.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0255091000
_diffrn_orient_matrix_UB_12      0.0676824000
_diffrn_orient_matrix_UB_13      0.0662008000
_diffrn_orient_matrix_UB_21      0.0515895000
_diffrn_orient_matrix_UB_22      0.0810517000
_diffrn_orient_matrix_UB_23      -0.0527001000
_diffrn_orient_matrix_UB_31      -0.1708322000
_diffrn_orient_matrix_UB_32      0.0346787000
_diffrn_orient_matrix_UB_33      -0.0060287000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0110
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9288
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.940
_diffrn_reflns_theta_min         4.012
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.506
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1645 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0267
_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^)+(0.0432P)^2^+0.3942P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0708
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.950
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                4023
_reflns_number_total             4069
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ICA-2020-511-119767.cif
_cod_data_source_block           ligand
_cod_original_cell_volume        2151.24(3)
_cod_database_code               1564149
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.753
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C10(H10), C17(H17), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C9(H9), C14(H14), C4(H4), C12(H12), C16(H16), C15(H15), C20(H20),
 C24(H24), C23(H23), C22(H22), C7(H7), C13(H13), C8(H8)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C6(H6A,H6B,H6C)
;
_shelx_res_checksum              82569
_shelx_hkl_checksum              19289