data_global

_publ_contact_author               'Andrei S.Batsanov'
_publ_contact_author_email          a.s.batsanov@durham.ac.uk
_publ_contact_author_id_orcid       0000-0002-4912-0981

loop_
    _publ_author_name
    _publ_author_address
 'Arkhipenko, Sergey' 
; Centre for Sustainable Chemical Processes 
 Department of Chemistry, University of Durham
 South Road, Durham DH1 3LE, United Kingdom 
;
 'Batsanov, Andrei S.' 
; Department of Chemistry, University of Durham
 South Road, Durham DH1 3LE, United Kingdom 
;
 'Sabatini, Marco T.'  
; Department of Chemistry, University College London,   
 Gower Street, London WC1E 6BT, United Kingdom 
;
 'Karaluka, Valerija'  
; Department of Chemistry, University College London,   
 Gower Street, London WC1E 6BT, United Kingdom 
;
 'Sheppard, Tom D.' 
; Department of Chemistry, University College London,   
 Gower Street, London WC1E 6BT, United Kingdom 
;
 'Rzepa, Henry S.'  
; Department of Chemistry, Imperial College London  
 South Kensington Campus, London SW7 2AZ   
 United Kingdom 
;
 'Whiting, Andrew'  
; Centre for Sustainable Chemical Processes 
 Department of Chemistry, University of Durham
 South Road, Durham DH1 3LE, United Kingdom 
;
_journal_name_full                 'Chemical Science'
_journal_volume                    '?'
_journal_page_first                '?'
_journal_page_last                 '?'
_journal_year                      '2017'
_database_code_depnum_ccdc_journal  ? 

_publ_section_title
; Mechanistic insights into the boron-catalysed direct amidation reaction
;

_publ_section_references
; 
Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H.
 (2015). Acta Cryst. A71, 59-75.

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. 

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8. 

Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst., 40, 786-790;

Palatinus, L. & van der Lee, A. (2008). J. Appl. Cryst. 41, 975-984;

Palatinus, L., Prathapa, S. J. & van Smaalen, S. (2012). J. Appl. Cryst. 45,
 575-580.

;

#======================================================================

data_7a_16srv413 
_database_code_depnum_ccdc_archive	1563950     

_audit_creation_date              2016-11-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;

_chemical_name_common             ?
_chemical_name_systematic         3,4,5-trifluorophenylboroxine
_chemical_formula_moiety          'C18 H6 B3 F9 O3'
_chemical_formula_sum             'C18 H6 B3 F9 O3'
_chemical_formula_weight          473.66
_chemical_melting_point           ?
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'

_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.
;
_space_group_crystal_system       'orthorhombic'
_space_group_IT_number            60
_space_group_name_H-M_alt         'P b c n'
_space_group_name_Hall            '-P 2n 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y+1/2, z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, y, -z+1/2'
 '-x, -y, -z'
 'x-1/2, y-1/2, -z-1/2'
 '-x-1/2, y-1/2, z'
 'x, -y, z-1/2'

_cell_length_a                    17.083(4)
_cell_length_b                    13.093(3)
_cell_length_c                    7.990(2)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1787.0(8)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     7348
_cell_measurement_temperature     120.0
_cell_measurement_theta_max       31.51
_cell_measurement_theta_min       2.38
_shelx_estimated_absorpt_T_max    0.979
_shelx_estimated_absorpt_T_min    0.974
_exptl_absorpt_coefficient_mu     0.177
_exptl_absorpt_correction_T_max   1.0000
_exptl_absorpt_correction_T_min   0.8873
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1096 before and 0.0711 after correction.
The Ratio of minimum to maximum transmission is 0.8873.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             'clear colourless'
_exptl_crystal_colour_lustre      clear
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.761
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        irregular
_exptl_crystal_F_000              936
_exptl_crystal_size_max           0.15
_exptl_crystal_size_mid           0.13
_exptl_crystal_size_min           0.12
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0792
_diffrn_reflns_av_unetI/netI      0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max        22
_diffrn_reflns_limit_h_min        -22
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_number             22891
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full         25.242
_diffrn_reflns_theta_max          27.996
_diffrn_reflns_theta_min          2.385
_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 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device        '3-circle diffractometer'
_diffrn_measurement_device_type   'Bruker D8 Venture'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_radiation_monochromator   'focusing mirrors'
_diffrn_radiation_probe           X-ray
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    'microfocus sealed X-ray tube'
_diffrn_source_type               'Incoatec I\mS microsource'
_diffrn_standards_number          0
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 1466
_reflns_number_total              2162
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing.bruker_data_scaling    'SADABS V2012/1 (Bruker AXS Inc.)'
_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 (Sheldrick, 2015)'
_computing_structure_solution     'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max          0.312
_refine_diff_density_min          -0.296
_refine_diff_density_rms          0.054
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.049
_refine_ls_hydrogen_treatment     refall
_refine_ls_matrix_type            full
_refine_ls_number_parameters      164
_refine_ls_number_reflns          2162
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0781
_refine_ls_R_factor_gt            0.0445
_refine_ls_restrained_S_all       1.049
_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)+(0.0600P)²+0.2500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1031
_refine_ls_wR_factor_ref          0.1170
_refine_special_details           ?
_olex2_refinement_description
;
;
_atom_sites_solution_hydrogens    difmap
_atom_sites_solution_primary      iterative
_atom_sites_solution_secondary    difmap
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
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 F1 F 0.33544(7) 0.35130(7) 0.46045(15) 0.0326(3) Uani 1 1 d . . . . .
 F2 F 0.22161(6) 0.44746(9) 0.29114(15) 0.0335(3) Uani 1 1 d . . . . .
 F3 F 0.21638(6) 0.65261(8) 0.27961(14) 0.0327(3) Uani 1 1 d . . . . .
 F4 F 0.39036(7) 1.16468(8) 0.57511(16) 0.0369(3) Uani 1 1 d . . . . .
 F5 F 0.5000 1.26713(11) 0.7500 0.0348(4) Uani 1 2 d S T P . .
 O1 O 0.44870(6) 0.78147(8) 0.64872(14) 0.0178(3) Uani 1 1 d . . . . .
 O2 O 0.5000 0.62463(13) 0.7500 0.0183(4) Uani 1 2 d S T P . .
 C1 C 0.38609(10) 0.61550(13) 0.5480(2) 0.0170(4) Uani 1 1 d . . . . .
 C2 C 0.38885(10) 0.50893(13) 0.5496(2) 0.0186(4) Uani 1 1 d . . . . .
 C3 C 0.33357(10) 0.45441(13) 0.4628(2) 0.0211(4) Uani 1 1 d . . . . .
 C4 C 0.27511(10) 0.50259(14) 0.3749(2) 0.0219(4) Uani 1 1 d . . . . .
 C5 C 0.27302(10) 0.60771(14) 0.3709(2) 0.0210(4) Uani 1 1 d . . . . .
 C6 C 0.32735(11) 0.66504(14) 0.4567(2) 0.0194(4) Uani 1 1 d . . . . .
 C7 C 0.5000 0.95231(17) 0.7500 0.0166(5) Uani 1 2 d S T P . .
 C8 C 0.44291(11) 1.00589(13) 0.6615(2) 0.0194(4) Uani 1 1 d . . . . .
 C9 C 0.44401(10) 1.11117(14) 0.6623(2) 0.0221(4) Uani 1 1 d . . . . .
 C10 C 0.5000 1.16430(18) 0.7500 0.0238(6) Uani 1 2 d S T P . .
 B1 B 0.44702(11) 0.67698(15) 0.6521(2) 0.0172(4) Uani 1 1 d . . . . .
 B2 B 0.5000 0.8344(2) 0.7500 0.0152(6) Uani 1 2 d S T P . .
 H2 H 0.4302(12) 0.4749(15) 0.609(2) 0.029(5) Uiso 1 1 d . . . . .
 H8 H 0.4018(10) 0.9701(13) 0.600(2) 0.013(4) Uiso 1 1 d . . . . .
 H6 H 0.3262(11) 0.7341(16) 0.451(2) 0.025(5) Uiso 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 F1 C3 1.350(2) . ?
 F2 C4 1.3432(19) . ?
 F3 C5 1.3468(19) . ?
 F4 C9 1.348(2) . ?
 F5 C10 1.346(3) . ?
 O1 B1 1.369(2) . ?
 O1 B2 1.3797(18) . ?
 O2 B1 1.379(2) 4_656 ?
 O2 B1 1.379(2) . ?
 C1 C2 1.396(2) . ?
 C1 C6 1.400(2) . ?
 C1 B1 1.556(3) . ?
 C2 C3 1.372(2) . ?
 C2 H2 0.96(2) . ?
 C3 C4 1.374(2) . ?
 C4 C5 1.377(3) . ?
 C5 C6 1.377(2) . ?
 C6 H6 0.91(2) . ?
 C7 C8 1.394(2) 4_656 ?
 C7 C8 1.394(2) . ?
 C7 B2 1.544(3) . ?
 C8 C9 1.379(2) . ?
 C8 H8 0.979(18) . ?
 C9 C10 1.375(2) . ?
 C10 C9 1.375(2) 4_656 ?
 B2 O1 1.3797(18) 4_656 ?

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
  _geom_angle_publ_flag
 B1 O1 B2 120.26(15) . . ?
 B1 O2 B1 120.4(2) 4_656 . ?
 C2 C1 C6 119.47(16) . . ?
 C2 C1 B1 119.31(15) . . ?
 C6 C1 B1 121.20(16) . . ?
 C1 C2 H2 119.5(12) . . ?
 C3 C2 C1 119.49(16) . . ?
 C3 C2 H2 121.0(12) . . ?
 F1 C3 C2 120.72(16) . . ?
 F1 C3 C4 117.97(15) . . ?
 C2 C3 C4 121.31(16) . . ?
 F2 C4 C3 120.15(16) . . ?
 F2 C4 C5 120.52(16) . . ?
 C3 C4 C5 119.31(16) . . ?
 F3 C5 C4 117.87(16) . . ?
 F3 C5 C6 121.06(16) . . ?
 C6 C5 C4 121.06(16) . . ?
 C1 C6 H6 120.3(13) . . ?
 C5 C6 C1 119.35(17) . . ?
 C5 C6 H6 120.4(13) . . ?
 C8 C7 C8 119.6(2) 4_656 . ?
 C8 C7 B2 120.22(11) . . ?
 C8 C7 B2 120.22(11) 4_656 . ?
 C7 C8 H8 121.1(10) . . ?
 C9 C8 C7 119.44(18) . . ?
 C9 C8 H8 119.4(10) . . ?
 F4 C9 C8 120.55(17) . . ?
 F4 C9 C10 118.27(17) . . ?
 C10 C9 C8 121.17(18) . . ?
 F5 C10 C9 120.39(11) . . ?
 F5 C10 C9 120.40(12) . 4_656 ?
 C9 C10 C9 119.2(2) . 4_656 ?
 O1 B1 O2 119.64(16) . . ?
 O1 B1 C1 121.36(16) . . ?
 O2 B1 C1 119.00(16) . . ?
 O1 B2 O1 119.7(2) . 4_656 ?
 O1 B2 C7 120.16(11) . . ?
 O1 B2 C7 120.16(11) 4_656 . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 C2 C1 B1 O1 177.16(16) . . . . ?
 C2 C1 B1 O2 -3.1(2) . . . . ?
 C6 C1 B1 O1 -4.6(3) . . . . ?
 C6 C1 B1 O2 175.11(15) . . . . ?
 C8 C7 B2 O1 -173.22(10) 4_656 . . . ?
 C8 C7 B2 O1 -173.22(10) . . . 4_656 ?
 C8 C7 B2 O1 6.78(10) 4_656 . . 4_656 ?
 C8 C7 B2 O1 6.78(10) . . . . ?
 B1 O1 B2 O1 1.91(11) . . . 4_656 ?
 B1 O1 B2 C7 -178.09(11) . . . . ?
 B1 O2 B1 O1 1.89(11) 4_656 . . . ?
 B1 O2 B1 C1 -177.84(18) 4_656 . . . ?
 B2 O1 B1 O2 -3.8(2) . . . . ?
 B2 O1 B1 C1 175.94(12) . . . . ?

_shelx_SHELXL_version_number      '2014/7'


#===END


