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_14srv091
_database_code_depnum_ccdc_archive	1563948     

_audit_creation_date              2017-07-23
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number      '2016/6'

_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       'monoclinic'
_space_group_IT_number            15
_space_group_name_H-M_alt         'C 1 2/c 1'
_space_group_name_Hall            '-C 2yc'
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'

_cell_length_a                    12.8358(9)
_cell_length_b                    12.6583(9)
_cell_length_c                    12.8851(9)
_cell_angle_alpha                 90
_cell_angle_beta                  119.060(2)
_cell_angle_gamma                 90
_cell_volume                      1830.0(2)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     3694
_cell_measurement_temperature     293
_cell_measurement_theta_max       29.94
_cell_measurement_theta_min       2.43
_shelx_estimated_absorpt_T_max    ?
_shelx_estimated_absorpt_T_min    ?
_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_absorpt_special_details    ?
_exptl_crystal_colour             colourless
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.719
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        block
_exptl_crystal_F_000              936
_exptl_crystal_size_max           0.541
_exptl_crystal_size_mid           0.226
_exptl_crystal_size_min           0.167
_exptl_special_details
;
 The data collection nominally covered full sphere of reciprocal 
space, by a combination of 3 runs of narrow-frame ω-scans (scan 
width 0.5° ω, 5s exposure), every run at a different φ angle. 
Crystal to detector distance 3.50 cm. 
  Phase transition on cooling below 210 K.
;
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_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_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_source                    'Incoatec I\mS microsource'
_diffrn_standards_number          0
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 1161
_reflns_number_total              1619
_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        '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)'
_refine_diff_density_max          0.183
_refine_diff_density_min          -0.133
_refine_diff_density_rms          0.045
_refine_ls_extinction_coef        .
_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_R_factor_all           0.0594
_refine_ls_R_factor_gt            0.0409
_refine_ls_restrained_S_all       1.078
_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
_refine_special_details           ?
_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)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      direct
_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 0.500000 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 . . . . .


_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 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_
  _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
 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) . . ?

_olex2_submission_special_instructions 'No special instructions were received'

#===END

