Nickel-Catalyzed Acetamidation and Lactamization of Arylboronic Acids
Huang, Bo; Zeng, Linwei; Shen, Yangyong; Cui, Sunliang; Chem. Commun.  (2017) –; doi:10.1039/C7CC07055A

data_7120756
_publ_section_title
;
 Nickel-Catalyzed Acetamidation and Lactamization of Arylboronic Acids
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC07055A
_journal_year                    2017
_chemical_formula_moiety         'C16 H17 N O3 S2'
_chemical_formula_sum            'C16 H17 N O3 S2'
_chemical_formula_weight         335.42
_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
_audit_creation_date             2017-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-07 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.337(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5885(10)
_cell_length_b                   6.0938(5)
_cell_length_c                   25.337(3)
_cell_measurement_reflns_used    2459
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2844
_cell_measurement_theta_min      3.2249
_cell_volume                     1624.9(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_details
;
  1 omega  -68.00  -14.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246  123.0000  -92.0000 54

  2 omega  -73.00    6.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246  -38.0000  -90.0000 79

  3 omega  -90.00  -64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246  156.0000  121.0000 26

  4 omega  -73.00   10.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246  -38.0000   30.0000 83

  5 omega  -24.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246   38.0000   90.0000 88

  6 omega  -29.00   63.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246   38.0000 -150.0000 92

  7 omega  -75.00   16.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246  -77.0000 -180.0000 91

  8 omega  -11.00   55.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246   38.0000    0.0000 66

  9 omega   49.00   74.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9371 -133.0000  127.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0279751000
_diffrn_orient_matrix_UB_12      0.0094223000
_diffrn_orient_matrix_UB_13      -0.0266697000
_diffrn_orient_matrix_UB_21      -0.0582895000
_diffrn_orient_matrix_UB_22      0.0318785000
_diffrn_orient_matrix_UB_23      0.0090689000
_diffrn_orient_matrix_UB_31      0.0190333000
_diffrn_orient_matrix_UB_32      0.1115424000
_diffrn_orient_matrix_UB_33      -0.0003454000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            4847
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.469
_diffrn_reflns_theta_min         3.236
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_refine_diff_density_max         2.206
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.412
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4847
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.412
_refine_ls_R_factor_all          0.1819
_refine_ls_R_factor_gt           0.1510
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3539
_refine_ls_wR_factor_ref         0.3724
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3203
_reflns_number_total             4847
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc07055a2.cif
_cod_data_source_block           170704_hb_7_50d_twin1_hklf4_pl
_cod_database_code               7120756
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h n o s'
_shelx_estimated_absorpt_t_max   0.888
_shelx_estimated_absorpt_t_min   0.852
_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. Others
 Sof(H10A)=Sof(C12A)=Sof(H12C)=Sof(H12D)=1-FVAR(1)
 Sof(H10)=Sof(C12)=Sof(H12A)=Sof(H12B)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C10(H10), C10(H10A)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B), C12(H12A,H12B), C12A(H12C,H12D)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C15(H15), C2(H2), C5(H5), C16(H16), C14(H14)
3.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              19302
_olex2_submission_special_instructions 'No special instructions were received'