#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/85/1548569.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1548569
loop_
_publ_author_name
'Arkhipenko, Sergey'
'Sabatini, Marco T.'
'Batsanov, Andrei S.'
'Karaluka, Valerija'
'Sheppard, Tom D.'
'Rzepa, Henry S.'
'Whiting, Andrew'
_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         'C18 H6 B3 F9 O3'
_chemical_formula_sum            'C18 H6 B3 F9 O3'
_chemical_formula_weight         473.66
_chemical_name_systematic        3,4,5-trifluorophenylboroxine
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-07-23
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_audit_update_record
;
2017-07-23 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.060(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8358(9)
_cell_length_b                   12.6583(9)
_cell_length_c                   12.8851(9)
_cell_measurement_reflns_used    3694
_cell_measurement_temperature    293
_cell_measurement_theta_max      29.94
_cell_measurement_theta_min      2.43
_cell_volume                     1830.0(2)
_computing_cell_refinement       'APEX2 v.2013.4_1 (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      293
_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 0.999
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω-scan
_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  0.0292
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9411
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.426
_diffrn_source                   'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6833
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1260 before and 0.0429 after correction.
The Ratio of minimum to maximum transmission is 0.9160.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
_exptl_crystal_size_max          0.541
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.167
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         1619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0607P)²+0.4114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1161
_reflns_number_total             1619
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7sc03595k2.cif
_cod_data_source_block           7a_14srv091
_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               1548569
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C10(H10)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
F1 F 0.500000 1.24681(13) 0.250000 0.0993(6) Uani 1 2 d S T P
F2 F 0.44405(14) 1.14143(10) 0.39628(13) 0.1033(5) Uani 1 1 d . . .
F3 F 0.26001(12) 0.62720(11) 0.55836(12) 0.0989(5) Uani 1 1 d . . .
F4 F 0.23598(10) 0.41788(11) 0.53833(11) 0.0891(5) Uani 1 1 d . . .
F5 F 0.30333(12) 0.31099(10) 0.40217(13) 0.0999(5) Uani 1 1 d . . .
O1 O 0.45189(10) 0.74477(10) 0.30832(10) 0.0607(4) Uani 1 1 d . . .
O2 O 0.500000 0.58253(13) 0.250000 0.0563(5) Uani 1 2 d S T P
C1 C 0.500000 1.1409(2) 0.250000 0.0659(7) Uani 1 2 d S T P
C2 C 0.47049(17) 1.08586(16) 0.32337(17) 0.0650(5) Uani 1 1 d . . .
C3 C 0.46848(15) 0.97819(15) 0.32341(15) 0.0603(5) Uani 1 1 d . . .
H3 H 0.445578 0.941606 0.373535 0.072 Uiso 1 1 calc R . .
C4 C 0.500000 0.9218(2) 0.250000 0.0538(6) Uani 1 2 d S T P
C5 C 0.38497(14) 0.57619(14) 0.36370(15) 0.0521(5) Uani 1 1 d . . .
C6 C 0.34678(16) 0.63052(15) 0.43310(16) 0.0609(5) Uani 1 1 d . . .
H6 H 0.355333 0.705098 0.440787 0.073 Uiso 1 1 calc R . .
C7 C 0.29705(16) 0.57683(17) 0.49015(17) 0.0638(5) Uani 1 1 d . . .
C8 C 0.28307(14) 0.46991(17) 0.48043(16) 0.0631(5) Uani 1 1 d . . .
C9 C 0.31879(16) 0.41619(15) 0.41081(18) 0.0635(5) Uani 1 1 d . . .
C10 C 0.36981(15) 0.46756(15) 0.35300(15) 0.0586(5) Uani 1 1 d . . .
H10 H 0.394707 0.428801 0.305748 0.070 Uiso 1 1 calc R . .
B1 B 0.500000 0.7998(2) 0.250000 0.0551(7) Uani 1 2 d S T P
B2 B 0.44702(17) 0.63658(17) 0.30458(17) 0.0536(5) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
B2 O1 B1 120.87(16) . .
B2 O2 B2 120.3(2) 2_655 .
F1 C1 C2 120.62(13) . .
F1 C1 C2 120.62(13) . 2_655
C2 C1 C2 118.8(3) . 2_655
F2 C2 C1 117.77(19) . .
F2 C2 C3 120.82(17) . .
C3 C2 C1 121.41(18) . .
C2 C3 C4 120.03(18) . .
C3 C4 C3 118.3(2) 2_655 .
C3 C4 B1 120.83(12) 2_655 .
C3 C4 B1 120.83(12) . .
C6 C5 B2 119.92(17) . .
C10 C5 C6 118.53(17) . .
C10 C5 B2 121.51(16) . .
C7 C6 C5 120.15(18) . .
F3 C7 C6 121.44(19) . .
F3 C7 C8 117.25(17) . .
C8 C7 C6 121.31(18) . .
F4 C8 C7 120.80(19) . .
F4 C8 C9 120.38(19) . .
C7 C8 C9 118.82(17) . .
F5 C9 C8 117.62(17) . .
F5 C9 C10 121.03(18) . .
C8 C9 C10 121.35(18) . .
C9 C10 C5 119.82(17) . .
O1 B1 O1 119.0(2) . 2_655
O1 B1 C4 120.52(12) 2_655 .
O1 B1 C4 120.52(12) . .
O1 B2 O2 119.33(17) . .
O1 B2 C5 120.17(16) . .
O2 B2 C5 120.49(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C1 1.341(3) .
F2 C2 1.343(2) .
F3 C7 1.346(2) .
F4 C8 1.339(2) .
F5 C9 1.343(2) .
O1 B1 1.372(2) .
O1 B2 1.371(2) .
O2 B2 1.375(2) .
O2 B2 1.375(2) 2_655
C1 C2 1.368(2) .
C1 C2 1.368(2) 2_655
C2 C3 1.363(3) .
C3 C4 1.393(2) .
C4 B1 1.544(4) .
C5 C6 1.392(2) .
C5 C10 1.386(2) .
C5 B2 1.545(3) .
C6 C7 1.366(2) .
C7 C8 1.363(3) .
C8 C9 1.370(3) .
C9 C10 1.371(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 20654586
