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_4a_15srv002 
_database_code_depnum_ccdc_archive	1551614     

_audit_creation_date              2015-01-05
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4975)
;

_chemical_name_common             ?
_chemical_name_systematic
;
 Bis-3,4,5-trifluorophenylborinic acid benzylamine complex  
;
_chemical_formula_moiety          'C19 H14 B F6 N O'
_chemical_formula_sum             'C19 H14 B F6 N O'
_chemical_formula_weight          397.12
_chemical_melting_point           393(2)
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'
 'N' 'N' 0.0061 0.0033 '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'
 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system       'triclinic'
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
loop_
  _space_group_symop_id
  _space_group_symop_operation_xyz
 1 'x, y, z'
 2 '-x, -y, -z'

_cell_length_a                    9.03430(10)
_cell_length_b                    10.2063(2)
_cell_length_c                    11.0348(2)
_cell_angle_alpha                 66.3381(18)
_cell_angle_beta                  70.1856(17)
_cell_angle_gamma                 78.1262(19)
_cell_volume                      873.89(3)
_cell_formula_units_Z             2
_cell_measurement_reflns_used     9905
_cell_measurement_temperature     120.0
_cell_measurement_theta_max       31.50
_cell_measurement_theta_min       2.19
_exptl_absorpt_coefficient_mu     0.136
_exptl_absorpt_correction_T_max   1.0000
_exptl_absorpt_correction_T_min   0.9474
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1035 before and 0.0427 after correction.
The Ratio of minimum to maximum transmission is 0.9474.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour             'clear colourless'
_exptl_crystal_colour_lustre      clear
_exptl_crystal_colour_modifier    .
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.509
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_description        block
_exptl_crystal_F_000              404
_exptl_crystal_size_max           0.45
_exptl_crystal_size_mid           0.44
_exptl_crystal_size_min           0.2
_exptl_special_details
;
 ? 
;
_diffrn_reflns_av_R_equivalents   0.0316
_diffrn_reflns_av_unetI/netI      0.0306
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_number             18051
_diffrn_reflns_theta_full         28.99
_diffrn_reflns_theta_max          28.99
_diffrn_reflns_theta_min          2.10
_diffrn_ambient_temperature       120.0
_diffrn_detector                  'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean  ?
_diffrn_detector_type             'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device        'Bruker D8 Venture'
_diffrn_measurement_device_type   D8Venture
_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                    'iMuS microsource'
_diffrn_standards_decay_%         ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_number          0
_reflns_number_gt                 3848
_reflns_number_total              4649
_reflns_threshold_expression      >2sigma(I)
_computing.bruker_data_scaling    'SADABS V2012/1 (Bruker AXS Inc.)'
_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   'XL (Sheldrick, 2008)'
_computing_structure_solution     'XS (Sheldrick, 2008)'
_refine_diff_density_max          0.418
_refine_diff_density_min          -0.278
_refine_diff_density_rms          0.053
_refine_ls_extinction_coef        ?
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.042
_refine_ls_hydrogen_treatment     refall
_refine_ls_matrix_type            full
_refine_ls_number_parameters      309
_refine_ls_number_reflns          4649
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0553
_refine_ls_R_factor_gt            0.0426
_refine_ls_restrained_S_all       1.042
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0450P)²+0.4500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1000
_refine_ls_wR_factor_ref          0.1073
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description
;
;
_atom_sites_solution_hydrogens    difmap
_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_calc_flag
  _atom_site_disorder_assembly
  _atom_site_disorder_group
  _atom_site_refinement_flags_posn
 F1 F -0.20075(12) 0.66672(10) 0.16511(11) 0.0412(3) Uani 1 d . . .
 F2 F 0.04691(13) 0.77102(9) -0.05566(9) 0.0335(2) Uani 1 d . . .
 F3 F 0.32604(12) 0.61085(11) -0.08381(9) 0.0396(3) Uani 1 d . . .
 F4 F 0.63163(11) 0.26659(10) 0.38904(10) 0.0334(2) Uani 1 d . . .
 F5 F 0.77197(9) 0.03468(11) 0.32070(9) 0.0330(2) Uani 1 d . . .
 F6 F 0.60311(10) -0.12271(10) 0.27953(10) 0.0308(2) Uani 1 d . . .
 O1 O 0.05580(11) 0.10150(9) 0.31688(9) 0.01477(19) Uani 1 d . . .
 N1 N -0.00144(13) 0.18774(11) 0.50154(11) 0.0135(2) Uani 1 d . . .
 C1 C 0.01192(16) 0.27091(14) 0.58187(14) 0.0184(3) Uani 1 d . . .
 C2 C -0.13048(17) 0.25231(15) 0.70628(14) 0.0214(3) Uani 1 d . . .
 C3 C -0.1303(2) 0.13788(17) 0.82935(15) 0.0285(3) Uani 1 d . . .
 C4 C -0.2675(3) 0.1112(2) 0.93912(18) 0.0418(5) Uani 1 d . . .
 C5 C -0.4036(2) 0.1987(2) 0.9268(2) 0.0473(5) Uani 1 d . . .
 C6 C -0.4049(2) 0.3141(2) 0.8063(2) 0.0443(5) Uani 1 d . . .
 C7 C -0.26766(19) 0.34075(18) 0.69556(18) 0.0313(3) Uani 1 d . . .
 C8 C 0.09581(15) 0.36735(13) 0.24121(12) 0.0143(2) Uani 1 d . . .
 C9 C -0.04806(16) 0.45144(14) 0.25229(14) 0.0195(3) Uani 1 d . . .
 C10 C -0.06249(17) 0.58543(14) 0.15298(15) 0.0227(3) Uani 1 d . . .
 C11 C 0.06228(19) 0.63966(14) 0.04019(14) 0.0227(3) Uani 1 d . . .
 C12 C 0.20382(18) 0.55781(15) 0.02747(13) 0.0229(3) Uani 1 d . . .
 C13 C 0.22200(16) 0.42413(14) 0.12590(13) 0.0192(3) Uani 1 d . . .
 C14 C 0.29679(14) 0.15348(13) 0.35124(12) 0.0139(2) Uani 1 d . . .
 C15 C 0.38706(16) 0.23236(14) 0.37516(13) 0.0180(3) Uani 1 d . . .
 C16 C 0.54424(16) 0.19097(15) 0.36580(14) 0.0220(3) Uani 1 d . . .
 C17 C 0.61746(15) 0.07319(16) 0.33190(13) 0.0220(3) Uani 1 d . . .
 C18 C 0.52957(15) -0.00580(15) 0.31023(13) 0.0202(3) Uani 1 d . . .
 C19 C 0.37194(15) 0.03288(14) 0.31846(13) 0.0161(2) Uani 1 d . . .
 B1 B 0.11586(16) 0.20366(14) 0.34713(14) 0.0124(2) Uani 1 d . . .
 H1 H 0.016(2) 0.140(2) 0.257(2) 0.035(5) Uiso 1 d . . .
 H1A H -0.102(2) 0.2086(18) 0.4936(17) 0.020(4) Uiso 1 d . . .
 H1B H -0.001(2) 0.0922(19) 0.5553(18) 0.023(4) Uiso 1 d . . .
 H1C H 0.0227(19) 0.3710(18) 0.5185(17) 0.021(4) Uiso 1 d . . .
 H1D H 0.110(2) 0.2338(18) 0.6113(17) 0.022(4) Uiso 1 d . . .
 H3 H -0.035(2) 0.077(2) 0.8367(19) 0.033(5) Uiso 1 d . . .
 H4 H -0.267(3) 0.026(3) 1.025(3) 0.062(7) Uiso 1 d . . .
 H5 H -0.498(3) 0.182(3) 1.000(3) 0.061(7) Uiso 1 d . . .
 H6 H -0.495(3) 0.377(3) 0.793(2) 0.053(6) Uiso 1 d . . .
 H7 H -0.266(2) 0.416(2) 0.610(2) 0.035(5) Uiso 1 d . . .
 H9 H -0.140(2) 0.4197(19) 0.3261(19) 0.027(4) Uiso 1 d . . .
 H13 H 0.322(2) 0.3737(19) 0.1124(18) 0.026(4) Uiso 1 d . . .
 H15 H 0.3441(18) 0.3166(17) 0.3971(16) 0.015(4) Uiso 1 d . . .
 H19 H 0.3159(19) -0.0218(18) 0.2975(17) 0.022(4) Uiso 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 C10 1.3475(17) . ?
 F2 C11 1.3491(14) . ?
 F3 C12 1.3465(16) . ?
 F4 C16 1.3533(15) . ?
 F5 C17 1.3470(15) . ?
 F6 C18 1.3511(16) . ?
 O1 B1 1.4588(16) . ?
 O1 H1 0.78(2) . ?
 N1 C1 1.4965(16) . ?
 N1 B1 1.6362(17) . ?
 N1 H1A 0.912(17) . ?
 N1 H1B 0.915(18) . ?
 C1 C2 1.5066(18) . ?
 C1 H1C 0.982(17) . ?
 C1 H1D 0.995(17) . ?
 C2 C3 1.391(2) . ?
 C2 C7 1.385(2) . ?
 C3 C4 1.391(2) . ?
 C3 H3 0.96(2) . ?
 C4 C5 1.375(3) . ?
 C4 H4 0.99(3) . ?
 C5 C6 1.379(3) . ?
 C5 H5 0.94(2) . ?
 C6 C7 1.396(2) . ?
 C6 H6 0.94(2) . ?
 C7 H7 0.95(2) . ?
 C8 C9 1.3993(18) . ?
 C8 C13 1.3968(18) . ?
 C8 B1 1.6253(17) . ?
 C9 C10 1.3815(18) . ?
 C9 H9 0.948(18) . ?
 C10 C11 1.371(2) . ?
 C11 C12 1.373(2) . ?
 C12 C13 1.3811(18) . ?
 C13 H13 0.942(18) . ?
 C14 C15 1.4034(17) . ?
 C14 C19 1.3978(18) . ?
 C14 B1 1.6196(18) . ?
 C15 C16 1.3764(19) . ?
 C15 H15 0.957(16) . ?
 C16 C17 1.374(2) . ?
 C17 C18 1.373(2) . ?
 C18 C19 1.3791(18) . ?
 C19 H19 0.959(17) . ?

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 H1 111.9(15) . . ?
 C1 N1 B1 122.88(10) . . ?
 C1 N1 H1A 106.6(10) . . ?
 C1 N1 H1B 108.8(11) . . ?
 B1 N1 H1A 106.3(10) . . ?
 B1 N1 H1B 107.9(11) . . ?
 H1A N1 H1B 102.6(15) . . ?
 N1 C1 C2 109.18(10) . . ?
 N1 C1 H1C 106.9(10) . . ?
 N1 C1 H1D 108.6(10) . . ?
 C2 C1 H1C 113.4(10) . . ?
 C2 C1 H1D 110.2(10) . . ?
 H1C C1 H1D 108.5(13) . . ?
 C3 C2 C1 120.21(13) . . ?
 C7 C2 C1 120.26(13) . . ?
 C7 C2 C3 119.26(14) . . ?
 C2 C3 H3 119.2(11) . . ?
 C4 C3 C2 120.17(17) . . ?
 C4 C3 H3 120.6(11) . . ?
 C3 C4 H4 119.1(15) . . ?
 C5 C4 C3 120.07(18) . . ?
 C5 C4 H4 120.8(15) . . ?
 C4 C5 C6 120.43(16) . . ?
 C4 C5 H5 121.0(15) . . ?
 C6 C5 H5 118.6(15) . . ?
 C5 C6 C7 119.69(19) . . ?
 C5 C6 H6 123.4(15) . . ?
 C7 C6 H6 116.9(15) . . ?
 C2 C7 C6 120.36(18) . . ?
 C2 C7 H7 118.1(12) . . ?
 C6 C7 H7 121.5(12) . . ?
 C9 C8 B1 122.87(11) . . ?
 C13 C8 C9 117.27(11) . . ?
 C13 C8 B1 119.58(11) . . ?
 C8 C9 H9 122.5(11) . . ?
 C10 C9 C8 120.72(13) . . ?
 C10 C9 H9 116.8(11) . . ?
 F1 C10 C9 120.46(13) . . ?
 F1 C10 C11 118.16(12) . . ?
 C11 C10 C9 121.38(13) . . ?
 F2 C11 C10 120.80(13) . . ?
 F2 C11 C12 120.68(13) . . ?
 C10 C11 C12 118.52(12) . . ?
 F3 C12 C11 118.46(12) . . ?
 F3 C12 C13 120.22(13) . . ?
 C11 C12 C13 121.32(13) . . ?
 C8 C13 H13 121.7(11) . . ?
 C12 C13 C8 120.80(13) . . ?
 C12 C13 H13 117.5(11) . . ?
 C15 C14 B1 122.96(11) . . ?
 C19 C14 C15 117.74(11) . . ?
 C19 C14 B1 119.08(11) . . ?
 C14 C15 H15 122.5(9) . . ?
 C16 C15 C14 120.33(13) . . ?
 C16 C15 H15 117.1(9) . . ?
 F4 C16 C15 120.51(14) . . ?
 F4 C16 C17 118.03(12) . . ?
 C17 C16 C15 121.46(13) . . ?
 F5 C17 C16 121.14(13) . . ?
 F5 C17 C18 120.24(13) . . ?
 C18 C17 C16 118.61(12) . . ?
 F6 C18 C17 117.68(12) . . ?
 F6 C18 C19 120.93(13) . . ?
 C17 C18 C19 121.39(13) . . ?
 C14 C19 H19 120.5(10) . . ?
 C18 C19 C14 120.44(12) . . ?
 C18 C19 H19 119.0(10) . . ?
 O1 B1 N1 101.20(9) . . ?
 O1 B1 C8 112.32(10) . . ?
 O1 B1 C14 109.92(10) . . ?
 C8 B1 N1 109.68(10) . . ?
 C14 B1 N1 110.77(10) . . ?
 C14 B1 C8 112.41(10) . . ?

loop_
  _geom_hbond_atom_site_label_D
  _geom_hbond_atom_site_label_H
  _geom_hbond_atom_site_label_A
  _geom_hbond_distance_DH
  _geom_hbond_distance_HA
  _geom_hbond_distance_DA
  _geom_hbond_angle_DHA
  _geom_hbond_site_symmetry_A
 O1 H1 F2 0.78(2) 2.26(2) 3.0280(12) 166.3(19) 2_565
 N1 H1B O1 0.915(18) 1.959(18) 2.8552(14) 165.8(15) 2_556

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
 C1 N1 B1 O1 179.38(10) . . . . ?
 C3 C2 C1 N1 88.08(15) . . . . ?
 C7 C2 C1 N1 -85.87(15) . . . . ?
 C8 B1 N1 C1 -61.81(14) . . . . ?
 C8 B1 C14 C15 52.70(15) . . . . ?
 C8 B1 C14 C19 -121.84(12) . . . . ?
 C9 C8 B1 O1 77.93(15) . . . . ?
 C9 C8 B1 N1 -33.78(16) . . . . ?
 C13 C8 B1 O1 -95.80(13) . . . . ?
 C13 C8 B1 N1 152.50(11) . . . . ?
 C14 B1 N1 C1 62.85(14) . . . . ?
 C14 B1 C8 C9 -157.48(12) . . . . ?
 C14 B1 C8 C13 28.80(16) . . . . ?
 C15 C14 B1 O1 178.60(11) . . . . ?
 C15 C14 B1 N1 -70.39(14) . . . . ?
 C19 C14 B1 O1 4.07(15) . . . . ?
 C19 C14 B1 N1 115.07(12) . . . . ?
 B1 N1 C1 C2 169.50(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'



#===END
