Mechanistic insights into boron-catalysed direct amidation reactions.
Arkhipenko, Sergey; Sabatini, Marco T.; Batsanov, Andrei S.; Karaluka, Valerija; Sheppard, Tom D.; Rzepa, Henry S.; Whiting, Andrew; Chemical science 9 (2018) 1058–1072; doi:10.1039/c7sc03595k

data_1548571
_publ_section_title
;
 Mechanistic insights into boron-catalysed direct amidation reactions.
;
_journal_issue                   4
_journal_name_full               'Chemical science'
_journal_page_first              1058
_journal_page_last               1072
_journal_paper_doi               10.1039/c7sc03595k
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C29 H28 B Cl2 N O2'
_chemical_formula_sum            'C29 H28 B Cl2 N O2'
_chemical_formula_weight         504.23
_chemical_melting_point          409.7(5)
_chemical_name_systematic
'Bis-(2-chlorophenyl)borinic acid benzylamine-4-phenylbutanoat '
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-19
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-08-09 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                101.570(3)
_cell_angle_beta                 99.773(2)
_cell_angle_gamma                98.085(3)
_cell_formula_units_Z            2
_cell_length_a                   9.2006(2)
_cell_length_b                   11.4729(4)
_cell_length_c                   13.1121(4)
_cell_measurement_reflns_used    4447
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.3480
_cell_measurement_theta_min      2.6960
_cell_volume                     1314.22(7)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32)'
_computing_data_collection
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.15
_diffrn_detector_type            'Sapphire3 CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -41.00   49.00   0.5000   52.5300
omega____ theta____ kappa____ phi______ frames
    -      -20.1554   57.0000   90.0000 180

  2 omega  -24.00   22.00   0.5000   52.5300
omega____ theta____ kappa____ phi______ frames
    -      -20.1554 -100.0000 -150.0000 92

  3 omega  -24.00   63.00   0.5000   52.5300
omega____ theta____ kappa____ phi______ frames
    -       20.7804 -100.0000   60.0000 174

  4 omega   35.00   97.00   0.5000   52.5300
omega____ theta____ kappa____ phi______ frames
    -       20.7804  178.0000 -150.0000 124

  5 omega   -1.00   90.00   0.5000   52.5300
omega____ theta____ kappa____ phi______ frames
    -       20.7804   57.0000  -30.0000 182

  6 omega   -5.00   93.00   0.5000   52.5300
omega____ theta____ kappa____ phi______ frames
    -       20.7804   38.0000 -120.0000 196

  7 omega   -5.00   93.00   0.5000   52.5300
omega____ theta____ kappa____ phi______ frames
    -       20.7804   38.0000  150.0000 196

  8 omega  -52.00   46.00   0.5000   52.5300
omega____ theta____ kappa____ phi______ frames
    -       20.7804  -38.0000 -150.0000 196
;
_diffrn_measurement_device       kappa-diffractometer
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0738281000
_diffrn_orient_matrix_UB_12      -0.0103236000
_diffrn_orient_matrix_UB_13      0.0095209000
_diffrn_orient_matrix_UB_21      -0.0295983000
_diffrn_orient_matrix_UB_22      -0.0054464000
_diffrn_orient_matrix_UB_23      -0.0546820000
_diffrn_orient_matrix_UB_31      -0.0000004000
_diffrn_orient_matrix_UB_32      -0.0630948000
_diffrn_orient_matrix_UB_33      -0.0100326000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18221
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.516
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
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    1.274
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         6009
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0540P)^2^+0.4430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1263
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4561
_reflns_number_total             6009
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc03595k2.cif
_cod_data_source_block           5d_16srv084
_cod_depositor_comments
'Adding full bibliography for 1548566--1548579.cif.'
_cod_original_cell_volume        1314.23(7)
_cod_database_code               1548571
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N(HA,HB), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27),
  C28(H28), C29(H29)
;
_shelx_shelxl_version_number     2014/7