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_1548572
_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         'C26 H18 B F6 N O2'
_chemical_formula_sum            'C26 H18 B F6 N O2'
_chemical_formula_weight         501.22
_chemical_melting_point          471.7(15)
_chemical_name_systematic
'Bis(3,4,5-trifluorophenyl)-borinic acid benzylaminobenzoat'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-07-15
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.04 svn.r3439 for OlexSys, GUI svn.r5361)
;
_audit_update_record
;
2017-07-23 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.6902(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1019(4)
_cell_length_b                   11.7656(5)
_cell_length_c                   19.5670(9)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.55
_cell_volume                     2259.56(17)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            29313
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.143
_diffrn_source                   'I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0617 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.9356.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       rhombohedron
_exptl_crystal_F_000             1024
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CDCl3'
_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.273
_exptl_crystal_size_min          0.243
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5189
_refine_ls_number_restraints     74
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0440P)^2^+1.0370P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0976
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4345
_reflns_number_total             5189
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc03595k2.cif
_cod_data_source_block           5b_15srv006
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '471.7(1.5)' was changed to
'471.7(15)' - precision was estimated.

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1548566--1548579.cif.
;
_cod_database_code               1548572
_shelx_shelxl_version_number     2016/6
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C4A-C3 \\sim C4-C3
 with sigma of 0.02
 C5-C4 \\sim C5A-C4A
 with sigma of 0.02
 C7-C2 \\sim C7A-C2
 with sigma of 0.02
 C7-C6 \\sim C7A-C6A
 with sigma of 0.02
 C6-C5 \\sim C6A-C5A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C4) = Uanis(C4A)
Uanis(C5) = Uanis(C5A)
Uanis(C6) = Uanis(C6A)
Uanis(C7) = Uanis(C7A)
4. Rigid body (RIGU) restrains
 C2, C3, C4, C5, C6, C7, C4A, C5A, C6A, C7A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=1-
 FVAR(1)
 Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=FVAR(1)
 Fixed Sof: H3B(0.6) H3A(0.4)
6.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3B), C3(H3A), C9(H9), C13(H13), C15(H15), C19(H19), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C4(H4), C5(H5), C6(H6), C7(H7), C4A(H4A),
 C5A(H5A), C6A(H6A), C7A(H7A)
;
_shelx_res_checksum              54374
_olex2_submission_special_instructions 'No special instructions were received'