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_S1_15srv265 
_database_code_depnum_ccdc_archive	1563951     

_audit_creation_date              2015-11-29
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;

_chemical_name_common             ?
_chemical_name_systematic         'Bis-(3,4,5-trifluorophenyl)borinic acid ethanolamine complex'
_chemical_formula_moiety          'C14 H10 B F6 N O'
_chemical_formula_sum             'C14 H10 B F6 N O'
_chemical_formula_weight          333.04
_chemical_melting_point            484(1)
_chemical_oxdiff_formula          'C14 H10 N O B F6'
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'
 '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'

_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            14
_space_group_name_H-M_alt         'P 1 21/c 1'
_space_group_name_Hall            '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                    9.7608(4)
_cell_length_b                    18.4124(10)
_cell_length_c                    15.5249(9)
_cell_angle_alpha                 90
_cell_angle_beta                  90.202(5)
_cell_angle_gamma                 90
_cell_volume                      2790.1(2)
_cell_formula_units_Z             8
_cell_measurement_reflns_used     4080
_cell_measurement_temperature     120
_cell_measurement_theta_max       30.6070
_cell_measurement_theta_min       2.3950
_shelx_estimated_absorpt_T_max    ?
_shelx_estimated_absorpt_T_min    ?
_exptl_absorpt_coefficient_mu     0.153
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_T_min   0.49558
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             'clear colourless'
_exptl_crystal_colour_lustre      clear
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.586
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        prism
_exptl_crystal_F_000              1344
_exptl_crystal_recrystallization_method
'The material was recrystallised from ethyacetate-pentane by slow evaporation'
_exptl_crystal_size_max           0.2982
_exptl_crystal_size_mid           0.1842
_exptl_crystal_size_min           0.1121
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0643
_diffrn_reflns_av_unetI/netI      0.0550
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_k_max        21
_diffrn_reflns_limit_k_min        -21
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_number             16064
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full         24.998
_diffrn_reflns_theta_max          24.998
_diffrn_reflns_theta_min          2.086
_diffrn_ambient_temperature       120
_diffrn_detector                  'CCD plate'
_diffrn_detector_area_resol_mean  16.15
_diffrn_detector_type             'Sapphire3 CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -101.00  -35.00   0.3000   17.1600
omega____ theta____ kappa____ phi______ frames
    -      -25.4620 -178.0000   60.0000 220

#__ type_ start__ end____ width___ exp.time_
  2 omega -102.00  -33.00   0.3000   17.1600
omega____ theta____ kappa____ phi______ frames
    -      -25.4620  178.0000  -90.0000 230

#__ type_ start__ end____ width___ exp.time_
  3 omega    6.00   94.20   0.3000   17.1600
omega____ theta____ kappa____ phi______ frames
    -       26.0870   57.0000 -150.0000 294

#__ type_ start__ end____ width___ exp.time_
  4 omega    6.00   39.90   0.3000   17.1600
omega____ theta____ kappa____ phi______ frames
    -       26.0870   57.0000  -30.0000 113

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   98.20   0.3000   17.1600
omega____ theta____ kappa____ phi______ frames
    -       26.0870   38.0000  120.0000 324
;
_diffrn_measurement_device        'four-circle diffractometer'
_diffrn_measurement_device_type
'Agilent Technologies, Gemini S Ultra kappa-diffractometer'
_diffrn_measurement_method        'ω scans'
_diffrn_orient_matrix_UB_11       -0.0177042000
_diffrn_orient_matrix_UB_12       -0.0266386000
_diffrn_orient_matrix_UB_13       0.0310046000
_diffrn_orient_matrix_UB_21       0.0419486000
_diffrn_orient_matrix_UB_22       -0.0256795000
_diffrn_orient_matrix_UB_23       -0.0214625000
_diffrn_orient_matrix_UB_31       0.0565898000
_diffrn_orient_matrix_UB_32       0.0107247000
_diffrn_orient_matrix_UB_33       0.0258354000
_diffrn_radiation_monochromator   graphite
_diffrn_radiation_probe           x-ray
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 4003
_reflns_number_total              4869
_reflns_odcompleteness_completeness 98.39
_reflns_odcompleteness_iscentric  1
_reflns_odcompleteness_theta      26.32
_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_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32)'
_computing_data_collection
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution     'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max          0.597
_refine_diff_density_min          -0.603
_refine_diff_density_rms          0.115
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.052
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      416
_refine_ls_number_reflns          4869
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0891
_refine_ls_R_factor_gt            0.0745
_refine_ls_restrained_S_all       1.052
_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/[σ²(Fo²)+(0.1260P)²+2.3540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1894
_refine_ls_wR_factor_ref          0.2107
_refine_special_details
;
 Refined as a 2-component twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.365(3) 0.635(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 N1B(H1BA,H1BB), C2B(H2BA,H2BB), C1B(H1BC,H1BD), N1A(H1AA,H1AB), C1A(H1AC,
 H1AD), C2A(H2AA,H2AB)
3.b Aromatic/amide H refined with riding coordinates:
 C8B(H8B), C10B(H10B), C4B(H4B), C14B(H14B), C8A(H8A), C14A(H14A), C10A(H10A),
 C4A(H4A)
;
_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
 O1B O 0.2586(3) 0.27135(16) 0.0863(2) 0.0271(7) Uani 1 1 d . . . . .
 F3B F 0.4442(3) 0.22317(18) 0.3922(2) 0.0444(8) Uani 1 1 d . . . . .
 N1B N 0.0433(4) 0.27462(19) 0.1610(3) 0.0263(9) Uani 1 1 d . . . . .
 H1BA H -0.0395 0.2597 0.1448 0.032 Uiso 1 1 calc R . . . .
 H1BB H 0.0460 0.2771 0.2183 0.032 Uiso 1 1 calc R . . . .
 F2B F 0.4139(3) 0.07890(18) 0.4177(2) 0.0454(8) Uani 1 1 d . . . . .
 F6B F 0.1356(4) 0.12748(18) -0.17654(19) 0.0509(9) Uani 1 1 d . . . . .
 F4B F -0.1889(3) 0.03963(16) 0.0220(2) 0.0434(8) Uani 1 1 d . . . . .
 F5B F -0.0880(4) 0.04568(18) -0.1420(2) 0.0516(9) Uani 1 1 d . . . . .
 C3B C 0.2333(5) 0.1780(3) 0.2056(3) 0.0263(10) Uani 1 1 d . . . . .
 F1B F 0.2615(4) 0.00026(16) 0.3058(2) 0.0470(8) Uani 1 1 d . . . . .
 C7B C 0.3687(5) 0.1844(3) 0.3352(3) 0.0343(11) Uani 1 1 d . . . . .
 C2B C 0.0760(5) 0.3476(3) 0.1216(3) 0.0296(11) Uani 1 1 d . . . . .
 H2BA H 0.1150 0.3803 0.1641 0.035 Uiso 1 1 calc R . . . .
 H2BB H -0.0054 0.3697 0.0970 0.035 Uiso 1 1 calc R . . . .
 C8B C 0.3101(5) 0.2188(3) 0.2653(3) 0.0299(11) Uani 1 1 d . . . . .
 H8B H 0.3212 0.2686 0.2577 0.036 Uiso 1 1 calc R . . . .
 C9B C 0.0951(5) 0.1665(2) 0.0533(3) 0.0267(10) Uani 1 1 d . . . . .
 C13B C 0.0861(6) 0.1263(3) -0.0949(3) 0.0374(12) Uani 1 1 d . . . . .
 C10B C -0.0194(5) 0.1223(3) 0.0698(3) 0.0288(10) Uani 1 1 d . . . . .
 H10B H -0.0558 0.1202 0.1251 0.035 Uiso 1 1 calc R . . . .
 C11B C -0.0777(5) 0.0820(3) 0.0045(3) 0.0324(11) Uani 1 1 d . . . . .
 B1B B 0.1634(5) 0.2186(3) 0.1247(3) 0.0247(11) Uani 1 1 d . . . . .
 C1B C 0.1803(5) 0.3294(3) 0.0516(3) 0.0301(10) Uani 1 1 d . . . . .
 H1BC H 0.1345 0.3146 -0.0011 0.036 Uiso 1 1 calc R . . . .
 H1BD H 0.2381 0.3710 0.0394 0.036 Uiso 1 1 calc R . . . .
 C4B C 0.2201(5) 0.1033(3) 0.2200(3) 0.0313(11) Uani 1 1 d . . . . .
 H4B H 0.1707 0.0751 0.1811 0.038 Uiso 1 1 calc R . . . .
 C5B C 0.2791(5) 0.0711(3) 0.2909(3) 0.0328(11) Uani 1 1 d . . . . .
 C6B C 0.3563(5) 0.1116(3) 0.3487(3) 0.0332(11) Uani 1 1 d . . . . .
 C12B C -0.0288(6) 0.0837(3) -0.0780(4) 0.0363(12) Uani 1 1 d . . . . .
 C14B C 0.1478(5) 0.1660(3) -0.0311(3) 0.0313(11) Uani 1 1 d . . . . .
 H14B H 0.2256 0.1931 -0.0437 0.038 Uiso 1 1 calc R . . . .
 O1A O 0.7534(3) 0.23092(17) 0.1484(2) 0.0281(7) Uani 1 1 d . . . . .
 F3A F 0.9308(3) 0.27349(17) -0.1654(2) 0.0451(8) Uani 1 1 d . . . . .
 F2A F 0.9481(4) 0.41942(18) -0.1765(2) 0.0483(9) Uani 1 1 d . . . . .
 C9A C 0.5909(5) 0.3384(2) 0.1783(3) 0.0262(10) Uani 1 1 d . . . . .
 N1A N 0.5418(4) 0.2294(2) 0.0710(3) 0.0276(9) Uani 1 1 d . . . . .
 H1AA H 0.4588 0.2455 0.0848 0.033 Uiso 1 1 calc R . . . .
 H1AB H 0.5471 0.2259 0.0139 0.033 Uiso 1 1 calc R . . . .
 F4A F 0.3343(3) 0.48203(18) 0.2003(2) 0.0530(9) Uani 1 1 d . . . . .
 F6A F 0.6157(4) 0.37739(18) 0.40909(19) 0.0488(9) Uani 1 1 d . . . . .
 C1A C 0.6719(5) 0.1730(3) 0.1819(3) 0.0297(10) Uani 1 1 d . . . . .
 H1AC H 0.6267 0.1877 0.2346 0.036 Uiso 1 1 calc R . . . .
 H1AD H 0.7280 0.1307 0.1937 0.036 Uiso 1 1 calc R . . . .
 F5A F 0.4180(4) 0.4735(2) 0.3652(2) 0.0546(10) Uani 1 1 d . . . . .
 C7A C 0.8696(5) 0.3146(3) -0.1033(3) 0.0316(11) Uani 1 1 d . . . . .
 C8A C 0.8020(4) 0.2815(2) -0.0358(3) 0.0275(10) Uani 1 1 d . . . . .
 H8A H 0.7990 0.2311 -0.0325 0.033 Uiso 1 1 calc R . . . .
 C14A C 0.6346(5) 0.3363(3) 0.2645(3) 0.0313(11) Uani 1 1 d . . . . .
 H14A H 0.7038 0.3043 0.2807 0.038 Uiso 1 1 calc R . . . .
 C10A C 0.4885(5) 0.3888(3) 0.1576(3) 0.0311(11) Uani 1 1 d . . . . .
 H10A H 0.4577 0.3926 0.1011 0.037 Uiso 1 1 calc R . . . .
 B1A B 0.6609(5) 0.2845(3) 0.1083(4) 0.0249(11) Uani 1 1 d . . . . .
 C4A C 0.7483(5) 0.3995(3) 0.0213(3) 0.0297(10) Uani 1 1 d . . . . .
 H4A H 0.7066 0.4290 0.0622 0.036 Uiso 1 1 calc R . . . .
 F1A F 0.8364(4) 0.50321(16) -0.0507(2) 0.0500(8) Uani 1 1 d . . . . .
 C3A C 0.7377(4) 0.3236(3) 0.0280(3) 0.0265(10) Uani 1 1 d . . . . .
 C13A C 0.5768(6) 0.3808(3) 0.3253(3) 0.0346(12) Uani 1 1 d . . . . .
 C2A C 0.5685(5) 0.1570(3) 0.1123(3) 0.0300(11) Uani 1 1 d . . . . .
 H2AA H 0.6050 0.1228 0.0708 0.036 Uiso 1 1 calc R . . . .
 H2AB H 0.4851 0.1371 0.1366 0.036 Uiso 1 1 calc R . . . .
 C5A C 0.8209(5) 0.4309(3) -0.0463(4) 0.0355(11) Uani 1 1 d . . . . .
 C11A C 0.4330(5) 0.4330(3) 0.2203(4) 0.0360(12) Uani 1 1 d . . . . .
 C6A C 0.8807(5) 0.3882(3) -0.1096(3) 0.0359(12) Uani 1 1 d . . . . .
 C12A C 0.4743(6) 0.4296(3) 0.3042(4) 0.0394(13) 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
 O1B B1B 1.472(6) . ?
 O1B C1B 1.419(5) . ?
 F3B C7B 1.353(6) . ?
 N1B C2B 1.511(6) . ?
 N1B B1B 1.662(6) . ?
 F2B C6B 1.349(6) . ?
 F6B C13B 1.358(6) . ?
 F4B C11B 1.364(6) . ?
 F5B C12B 1.344(6) . ?
 C3B C8B 1.408(7) . ?
 C3B B1B 1.611(7) . ?
 C3B C4B 1.399(7) . ?
 F1B C5B 1.337(6) . ?
 C7B C8B 1.379(7) . ?
 C7B C6B 1.363(7) . ?
 C2B C1B 1.529(7) . ?
 C9B C10B 1.407(7) . ?
 C9B B1B 1.608(7) . ?
 C9B C14B 1.410(7) . ?
 C13B C12B 1.395(8) . ?
 C13B C14B 1.368(7) . ?
 C10B C11B 1.378(7) . ?
 C11B C12B 1.369(8) . ?
 C4B C5B 1.375(7) . ?
 C5B C6B 1.387(7) . ?
 O1A C1A 1.428(6) . ?
 O1A B1A 1.474(6) . ?
 F3A C7A 1.365(6) . ?
 F2A C6A 1.359(6) . ?
 C9A C14A 1.403(7) . ?
 C9A C10A 1.400(7) . ?
 C9A B1A 1.625(7) . ?
 N1A B1A 1.647(6) . ?
 N1A C2A 1.501(6) . ?
 F4A C11A 1.356(6) . ?
 F6A C13A 1.355(6) . ?
 C1A C2A 1.506(7) . ?
 F5A C12A 1.363(6) . ?
 C7A C8A 1.383(7) . ?
 C7A C6A 1.362(7) . ?
 C8A C3A 1.408(7) . ?
 C14A C13A 1.373(7) . ?
 C10A C11A 1.380(7) . ?
 B1A C3A 1.625(7) . ?
 C4A C3A 1.406(7) . ?
 C4A C5A 1.393(7) . ?
 F1A C5A 1.341(6) . ?
 C13A C12A 1.383(8) . ?
 C5A C6A 1.390(8) . ?
 C11A C12A 1.363(8) . ?

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
 C1B O1B B1B 108.1(3) . . ?
 C2B N1B B1B 105.3(3) . . ?
 C8B C3B B1B 119.3(4) . . ?
 C4B C3B C8B 118.0(4) . . ?
 C4B C3B B1B 122.8(4) . . ?
 F3B C7B C8B 119.7(5) . . ?
 F3B C7B C6B 117.8(5) . . ?
 C6B C7B C8B 122.5(5) . . ?
 N1B C2B C1B 103.6(4) . . ?
 C7B C8B C3B 119.4(5) . . ?
 C10B C9B B1B 123.1(4) . . ?
 C10B C9B C14B 117.3(4) . . ?
 C14B C9B B1B 119.6(4) . . ?
 F6B C13B C12B 118.3(5) . . ?
 F6B C13B C14B 120.6(5) . . ?
 C14B C13B C12B 121.1(5) . . ?
 C11B C10B C9B 120.2(5) . . ?
 F4B C11B C10B 119.2(5) . . ?
 F4B C11B C12B 118.6(5) . . ?
 C12B C11B C10B 122.1(5) . . ?
 O1B B1B N1B 100.0(3) . . ?
 O1B B1B C3B 110.9(4) . . ?
 O1B B1B C9B 112.0(4) . . ?
 C3B B1B N1B 108.7(4) . . ?
 C9B B1B N1B 108.2(3) . . ?
 C9B B1B C3B 115.8(4) . . ?
 O1B C1B C2B 104.8(4) . . ?
 C5B C4B C3B 120.8(5) . . ?
 F1B C5B C4B 120.4(4) . . ?
 F1B C5B C6B 118.8(4) . . ?
 C4B C5B C6B 120.8(4) . . ?
 F2B C6B C7B 121.6(5) . . ?
 F2B C6B C5B 119.9(5) . . ?
 C7B C6B C5B 118.4(4) . . ?
 F5B C12B C13B 119.8(5) . . ?
 F5B C12B C11B 121.9(5) . . ?
 C11B C12B C13B 118.2(5) . . ?
 C13B C14B C9B 121.0(5) . . ?
 C1A O1A B1A 108.2(3) . . ?
 C14A C9A B1A 119.6(4) . . ?
 C10A C9A C14A 116.9(4) . . ?
 C10A C9A B1A 123.6(4) . . ?
 C2A N1A B1A 106.0(3) . . ?
 O1A C1A C2A 105.0(4) . . ?
 F3A C7A C8A 120.1(5) . . ?
 C6A C7A F3A 117.8(4) . . ?
 C6A C7A C8A 122.1(5) . . ?
 C7A C8A C3A 120.3(4) . . ?
 C13A C14A C9A 121.0(5) . . ?
 C11A C10A C9A 120.7(5) . . ?
 O1A B1A C9A 112.6(4) . . ?
 O1A B1A N1A 99.5(3) . . ?
 O1A B1A C3A 109.7(4) . . ?
 C9A B1A N1A 108.3(4) . . ?
 C9A B1A C3A 116.0(4) . . ?
 C3A B1A N1A 109.3(4) . . ?
 C5A C4A C3A 120.4(4) . . ?
 C8A C3A B1A 120.3(4) . . ?
 C4A C3A C8A 117.6(4) . . ?
 C4A C3A B1A 122.1(4) . . ?
 F6A C13A C14A 121.2(5) . . ?
 F6A C13A C12A 117.2(4) . . ?
 C14A C13A C12A 121.6(5) . . ?
 N1A C2A C1A 104.3(4) . . ?
 F1A C5A C4A 120.6(5) . . ?
 F1A C5A C6A 118.5(4) . . ?
 C6A C5A C4A 120.9(5) . . ?
 F4A C11A C10A 120.8(5) . . ?
 F4A C11A C12A 117.2(5) . . ?
 C12A C11A C10A 122.0(5) . . ?
 F2A C6A C7A 120.9(5) . . ?
 F2A C6A C5A 120.5(5) . . ?
 C7A C6A C5A 118.6(5) . . ?
 F5A C12A C13A 120.9(5) . . ?
 F5A C12A C11A 121.2(5) . . ?
 C11A C12A C13A 117.9(5) . . ?

_shelx_SHELXL_version_number      '2014/7'
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
  _exptl_oxdiff_crystal_face_indexfrac_h
  _exptl_oxdiff_crystal_face_indexfrac_k
  _exptl_oxdiff_crystal_face_indexfrac_l
  _exptl_oxdiff_crystal_face_x
  _exptl_oxdiff_crystal_face_y
  _exptl_oxdiff_crystal_face_z
 0 1 0 0.0561 0.0008 1.0005 -0.0003 -0.0267 -0.0257 0.0108
 0 -1 0 0.0561 -0.0008 -1.0005 0.0003 0.0267 0.0257 -0.0108
 0 1 -2 0.0858 0.0012 1.0004 -1.9996 -0.0887 0.0173 -0.0409
 0 -1 2 0.0858 -0.0012 -1.0004 1.9996 0.0887 -0.0173 0.0409
 0 -1 -2 0.0840 -0.0004 -1.0006 -1.9989 -0.0353 0.0686 -0.0624
 0 1 2 0.0840 0.0004 1.0006 1.9989 0.0353 -0.0686 0.0624
 1 0 0 0.1488 1.0004 -0.0043 -0.0008 -0.0176 0.0421 0.0565
 -1 0 0 0.1488 -1.0004 0.0043 0.0008 0.0176 -0.0421 -0.0565

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perflourotether oil'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
  _twin_individual_id
  _twin_individual_mass_fraction_refined
 1 0.365(3)
 2 0.635(3)


#===END

