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_1548570
_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         'C28 H22 B2 I2 O5'
_chemical_formula_sum            'C28 H22 B2 I2 O5'
_chemical_formula_weight         713.87
_chemical_melting_point          382(1)
_chemical_name_systematic
'Di-2-iodophenylboronic B-O-B di-2-phenylacetate '
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-11-17
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                83.1389(18)
_cell_angle_beta                 87.0947(19)
_cell_angle_gamma                64.1817(17)
_cell_formula_units_Z            2
_cell_length_a                   10.6350(5)
_cell_length_b                   11.4814(5)
_cell_length_c                   12.2457(6)
_cell_measurement_reflns_used    9017
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.29
_cell_measurement_theta_min      2.45
_cell_volume                     1336.36(11)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '3-circle 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  0.0289
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21913
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         2.453
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.390
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0629 before and 0.0493 after correction.
The Ratio of minimum to maximum transmission is 0.8689.
The \l/2 correction factor is Not present.
;
_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    1.774
_exptl_crystal_description       prism
_exptl_crystal_F_000             692
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform, pentane'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.830
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         7764
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0200P)^2^+0.9000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0538
_refine_ls_wR_factor_ref         0.0580
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6143
_reflns_number_total             7764
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc03595k2.cif
_cod_data_source_block           11d_16srv431
_cod_depositor_comments
;
The following automatic conversions were performed:

'_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               1548570
_shelx_estimated_absorpt_t_max   0.890
_shelx_estimated_absorpt_t_min   0.621
_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.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28)
;
_shelx_shelxl_version_number     2014/7