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_1548573
_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         'C14 H13 B F6 N2 O,0.5(C D Cl3)'
_chemical_formula_sum            'C14.5 H13 B Cl1.5 D0.5 F6 N2 O'
_chemical_formula_weight         410.26
_chemical_melting_point          364(3)
_chemical_name_systematic
' Bis-3,4,5-trifluorophenylborinic acid ethylenediamine complex '
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.3307(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7500(5)
_cell_length_b                   11.0269(4)
_cell_length_c                   13.1973(5)
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.27
_cell_measurement_theta_min      2.42
_cell_volume                     1695.95(11)
_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 2014/7 multi-CPU version (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_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  0.0288
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            35272
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.325
_diffrn_reflns_theta_min         2.415
_diffrn_source                   'ImuS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1159 before and 0.0452 after correction.
The Ratio of minimum to maximum transmission is 0.9440.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.481
_exptl_crystal_size_mid          0.336
_exptl_crystal_size_min          0.274
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.39(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         9254
_refine_ls_number_restraints     57
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0770P)^2^+0.7700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1267
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                8294
_reflns_number_total             9254
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc03595k2.cif
_cod_data_source_block           4b_15srv104
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '363.7(2.5)' was changed to '364(3)'
- 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               1548573
_shelx_estimated_absorpt_t_max   0.905
_shelx_estimated_absorpt_t_min   0.841
_exptl_twin_twinlaw_details      '-1 0 0 0 -1 0 0 0 -1'
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.61(10) 0.39(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
3. Restrained distances
 C6A-C1 \\sim C6B-C1
 with sigma of 0.02
 C4A-C3 \\sim C4B-C3
 with sigma of 0.02
 F2A-C4A \\sim F2B-C4B
 with sigma of 0.02
 Cl4-C1S \\sim Cl2-C1S \\sim Cl3-C1S \\sim Cl5-C1S \\sim Cl1-C1S \\sim Cl8-C2S
\\sim Cl6-C2S \\sim Cl7-C2S
 with sigma of 0.02
 C6A-C5A \\sim C6B-C5B
 with sigma of 0.02
 C5A-C4A \\sim C5B-C4B
 with sigma of 0.02
 F3A-C5A \\sim F3B-C5B
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uiso(C6A) = Uiso(C6B)
Uiso(C4B) = Uiso(C4A)
Uanis(F2A) = Uanis(F2B)
Uanis(F3A) = Uanis(F3B)
Uanis(C2S) = Uanis(C1S)
Uanis(C5B) = Uanis(C5A)
5. Rigid body (RIGU) restrains
 F1, C1, C2, C3, F2A, F3A, C4A, C5A, C6A, F2B, F3B, C4B, C5B, C6B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(F2B)=Sof(F3B)=Sof(C4B)=Sof(C5B)=Sof(C6B)=Sof(H6B)=1-FVAR(1)
 Sof(F2A)=Sof(F3A)=Sof(C4A)=Sof(C5A)=Sof(C6A)=Sof(H6A)=FVAR(1)
 Fixed Sof: Cl6(0.15) Cl7(0.15) Cl8(0.15) C2S(0.15) D2(0.15) C1S(0.85)
 D1(0.85) Cl1(0.85) Cl2(0.7) Cl3(0.7) Cl4(0.15) Cl5(0.15)
7.a Riding coordinates:
 C2S(D2), C1S(D1), C6A(H6A), C6B(H6B)
7.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C7(H7A,H7B), C8(H8A,H8B)
7.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C22(H22), C26(H26), C2(H2), C10(H10), C14(H14)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'