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_S3_16srv264 
_database_code_depnum_ccdc_archive	1563953     

_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         'Bis-(2-chloro-4-fluorophenyl)borinic acid ethanolamine complex'
_chemical_formula_moiety          'C14 H12 B Cl2 F2 N O'
_chemical_formula_sum             'C14 H12 B Cl2 F2 N O'
_chemical_formula_weight          329.96
_chemical_melting_point           462(1)
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'
 'Cl' 'Cl' 0.1484 0.1585 '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                    23.6856(14)
_cell_length_b                    18.9704(11)
_cell_length_c                    9.8173(6)
_cell_angle_alpha                 90
_cell_angle_beta                  92.977(2)
_cell_angle_gamma                 90
_cell_volume                      4405.2(5)
_cell_formula_units_Z             12
_cell_measurement_reflns_used     9590
_cell_measurement_temperature     120
_cell_measurement_theta_max       32.75
_cell_measurement_theta_min       2.34
_shelx_estimated_absorpt_T_max    0.956
_shelx_estimated_absorpt_T_min    0.770
_exptl_absorpt_coefficient_mu     0.459
_exptl_absorpt_correction_T_max   1.0000
_exptl_absorpt_correction_T_min   0.8460
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1619 before and 0.0690 after correction.
The Ratio of minimum to maximum transmission is 0.8460.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             colourless
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.493
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        lathe
_exptl_crystal_F_000              2016
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 1.00 0.00 0.00 0.0210
 -1.00 0.00 0.00 0.0600
 0.00 1.00 -1.00 0.2190
 0.00 -1.00 1.00 0.2200
 0.00 -1.00 0.00 0.0590
 0.00 1.00 0.00 0.1010
 0.00 0.00 -1.00 0.2160
 -2.00 1.00 0.00 0.0490

_exptl_crystal_size_max           0.599
_exptl_crystal_size_mid           0.194
_exptl_crystal_size_min           0.098
_exptl_special_details
;
 Data were collected in shutterless mode. Full sphere of reciprocal 
space was nominally covered by 4 runs of 340 narrow-frame ω-scans (scan 
width 0.5°, 10s exposure), every run at a different φ angle.
Two runs of 358 φ-scans (scan width 1°, 1.5s exposure) were used for 
scaling overflowing intensities. Crystal to detector distance 3.50 cm.
;
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0600
_diffrn_reflns_av_unetI/netI      0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max        35
_diffrn_reflns_limit_h_min        -35
_diffrn_reflns_limit_k_max        28
_diffrn_reflns_limit_k_min        -28
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_number             112010
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full         32.500
_diffrn_reflns_theta_max          32.577
_diffrn_reflns_theta_min          2.029
_diffrn_ambient_temperature       120
_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   D8V_Mo
_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                 12293
_reflns_number_total              16035
_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        'SAINT v8.37A (Bruker, 2016)'
_computing_data_collection        'APEX3 v.2016.1-0 (Bruker, 2016)'
_computing_data_reduction         'SAINT v8.37A (Bruker, 2016)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'ShelXL 2016/6 multi-CPU (Sheldrick, 2015)'
_computing_structure_solution     'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max          0.831
_refine_diff_density_min          -0.642
_refine_diff_density_rms          0.068
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.034
_refine_ls_hydrogen_treatment     mixed
_refine_ls_matrix_type            full
_refine_ls_number_parameters      592
_refine_ls_number_reflns          16035
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0679
_refine_ls_R_factor_gt            0.0452
_refine_ls_restrained_S_all       1.034
_refine_ls_shift/su_max           0.002
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0470P)²+2.3330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1021
_refine_ls_wR_factor_ref          0.1113
_refine_special_details
;
 Amino H atoms - refall, other H atoms - riding (constr).
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1A(H1AC,H1AD), C2A(H2AA,H2AB), C1B(H1BC,H1BD), C2B(H2BA,H2BB), C1C(H1CC,
 H1CD), C2C(H2CA,H2CB)
2.b Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C7A(H7A), C8A(H8A), C11A(H11A), C13A(H13A), C14A(H14A), C5B(H5B),
 C7B(H7B), C8B(H8B), C11B(H11B), C13B(H13B), C14B(H14B), C5C(H5C), C7C(H7C),
 C8C(H8C), C11C(H11C), C13C(H13C), C14C(H14C)
;
_atom_sites_solution_hydrogens    mixed
_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
 Cl1A Cl 0.12517(2) 0.09063(2) 0.20158(4) 0.02545(8) Uani 1 1 d . . . . .
 Cl2A Cl 0.21290(2) 0.30599(2) 0.47806(4) 0.02504(8) Uani 1 1 d . . . . .
 F1A F -0.06099(5) -0.01554(6) 0.31221(13) 0.0427(3) Uani 1 1 d . . . . .
 F2A F 0.29131(4) 0.09810(5) 0.73744(12) 0.0374(3) Uani 1 1 d . . . . .
 O1A O 0.07408(4) 0.26500(5) 0.50537(9) 0.01570(18) Uani 1 1 d . . . . .
 N1A N 0.11097(5) 0.25623(6) 0.28287(12) 0.0165(2) Uani 1 1 d . . . . .
 H1AA H 0.1465(8) 0.2629(10) 0.2713(19) 0.023(5) Uiso 1 1 d . . . . .
 H1AB H 0.0981(8) 0.2375(11) 0.208(2) 0.032(5) Uiso 1 1 d . . . . .
 C1A C 0.08419(6) 0.32675(8) 0.30263(15) 0.0215(3) Uani 1 1 d . . . . .
 H1AC H 0.062218 0.341766 0.219104 0.026 Uiso 1 1 calc R . . . .
 H1AD H 0.113136 0.362946 0.326594 0.026 Uiso 1 1 calc R . . . .
 C2A C 0.04586(6) 0.31506(8) 0.41902(14) 0.0199(3) Uani 1 1 d . . . . .
 H2AA H 0.039954 0.359664 0.468673 0.024 Uiso 1 1 calc R . . . .
 H2AB H 0.008661 0.296750 0.384647 0.024 Uiso 1 1 calc R . . . .
 C3A C 0.05338(6) 0.14865(7) 0.37930(13) 0.0162(2) Uani 1 1 d . . . . .
 C4A C 0.06240(6) 0.09325(8) 0.28955(15) 0.0199(3) Uani 1 1 d . . . . .
 C5A C 0.02505(7) 0.03746(8) 0.26567(17) 0.0270(3) Uani 1 1 d . . . . .
 H5A H 0.033029 0.000424 0.204449 0.032 Uiso 1 1 calc R . . . .
 C6A C -0.02405(7) 0.03847(8) 0.33500(18) 0.0285(3) Uani 1 1 d . . . . .
 C7A C -0.03695(6) 0.09107(9) 0.42382(17) 0.0263(3) Uani 1 1 d . . . . .
 H7A H -0.071352 0.090515 0.469446 0.032 Uiso 1 1 calc R . . . .
 C8A C 0.00213(6) 0.14543(8) 0.44494(15) 0.0197(3) Uani 1 1 d . . . . .
 H8A H -0.006288 0.182050 0.506684 0.024 Uiso 1 1 calc R . . . .
 C9A C 0.15623(5) 0.17967(7) 0.49722(13) 0.0149(2) Uani 1 1 d . . . . .
 C10A C 0.20524(6) 0.21851(7) 0.53200(14) 0.0175(2) Uani 1 1 d . . . . .
 C11A C 0.25104(6) 0.19253(8) 0.61123(15) 0.0218(3) Uani 1 1 d . . . . .
 H11A H 0.283473 0.220756 0.632096 0.026 Uiso 1 1 calc R . . . .
 C12A C 0.24756(6) 0.12436(8) 0.65822(16) 0.0237(3) Uani 1 1 d . . . . .
 C13A C 0.20141(6) 0.08226(8) 0.62865(16) 0.0220(3) Uani 1 1 d . . . . .
 H13A H 0.199873 0.035359 0.662170 0.026 Uiso 1 1 calc R . . . .
 C14A C 0.15692(6) 0.11052(7) 0.54793(14) 0.0180(2) Uani 1 1 d . . . . .
 H14A H 0.125196 0.081265 0.525925 0.022 Uiso 1 1 calc R . . . .
 B1A B 0.09890(6) 0.21043(8) 0.41962(15) 0.0143(3) Uani 1 1 d . . . . .
 Cl1B Cl 0.46896(2) 0.09827(2) 0.12053(4) 0.02966(9) Uani 1 1 d . . . . .
 Cl2B Cl 0.55606(2) 0.28870(2) 0.40064(4) 0.02663(8) Uani 1 1 d . . . . .
 F1B F 0.27168(6) -0.00001(8) 0.12687(16) 0.0664(4) Uani 1 1 d . . . . .
 F2B F 0.61277(4) 0.08423(5) 0.69778(11) 0.0325(2) Uani 1 1 d . . . . .
 O1B O 0.40392(4) 0.25063(6) 0.45071(10) 0.0194(2) Uani 1 1 d . . . . .
 N1B N 0.44383(5) 0.26013(6) 0.23089(12) 0.0170(2) Uani 1 1 d . . . . .
 H1BA H 0.4800(9) 0.2682(11) 0.218(2) 0.034(5) Uiso 1 1 d . . . . .
 H1BB H 0.4295(9) 0.2439(12) 0.148(2) 0.039(6) Uiso 1 1 d . . . . .
 C1B C 0.41529(7) 0.32743(8) 0.26865(15) 0.0230(3) Uani 1 1 d . . . . .
 H1BC H 0.394633 0.348587 0.188467 0.028 Uiso 1 1 calc R . . . .
 H1BD H 0.443064 0.362004 0.307134 0.028 Uiso 1 1 calc R . . . .
 C2B C 0.37470(6) 0.30445(8) 0.37513(15) 0.0222(3) Uani 1 1 d . . . . .
 H2BA H 0.365585 0.344379 0.435092 0.027 Uiso 1 1 calc R . . . .
 H2BB H 0.339152 0.286028 0.331085 0.027 Uiso 1 1 calc R . . . .
 C3B C 0.38897(6) 0.14462(8) 0.28920(14) 0.0189(3) Uani 1 1 d . . . . .
 C4B C 0.40128(6) 0.09737(8) 0.18669(15) 0.0223(3) Uani 1 1 d . . . . .
 C5B C 0.36299(8) 0.04814(9) 0.13083(18) 0.0332(4) Uani 1 1 d . . . . .
 H5B H 0.373178 0.016550 0.061146 0.040 Uiso 1 1 calc R . . . .
 C6B C 0.30989(8) 0.04726(10) 0.1809(2) 0.0398(5) Uani 1 1 d . . . . .
 C7B C 0.29420(7) 0.09144(11) 0.2819(2) 0.0378(4) Uani 1 1 d . . . . .
 H7B H 0.257221 0.089592 0.314852 0.045 Uiso 1 1 calc R . . . .
 C8B C 0.33393(6) 0.13912(9) 0.33507(17) 0.0275(3) Uani 1 1 d . . . . .
 H8B H 0.323367 0.169629 0.406149 0.033 Uiso 1 1 calc R . . . .
 C9B C 0.48806(5) 0.17198(7) 0.43413(13) 0.0147(2) Uani 1 1 d . . . . .
 C10B C 0.53996(6) 0.20493(7) 0.46552(14) 0.0164(2) Uani 1 1 d . . . . .
 C11B C 0.58275(6) 0.17616(8) 0.55059(15) 0.0195(3) Uani 1 1 d . . . . .
 H11B H 0.617869 0.199701 0.566542 0.023 Uiso 1 1 calc R . . . .
 C12B C 0.57227(6) 0.11230(8) 0.61080(15) 0.0202(3) Uani 1 1 d . . . . .
 C13B C 0.52250(6) 0.07651(7) 0.58755(15) 0.0207(3) Uani 1 1 d . . . . .
 H13B H 0.515919 0.032771 0.631084 0.025 Uiso 1 1 calc R . . . .
 C14B C 0.48189(6) 0.10655(7) 0.49779(15) 0.0182(3) Uani 1 1 d . . . . .
 H14B H 0.447866 0.081090 0.478529 0.022 Uiso 1 1 calc R . . . .
 B1B B 0.43214(6) 0.20438(8) 0.35434(15) 0.0155(3) Uani 1 1 d . . . . .
 Cl1C Cl 0.79044(2) 0.09384(2) 0.50991(4) 0.02735(8) Uani 1 1 d . . . . .
 Cl2C Cl 0.88825(2) 0.28762(2) 0.22912(4) 0.02622(8) Uani 1 1 d . . . . .
 F1C F 0.60111(5) -0.00768(6) 0.36161(16) 0.0578(4) Uani 1 1 d . . . . .
 F2C F 0.94884(4) 0.06852(6) -0.00703(12) 0.0410(3) Uani 1 1 d . . . . .
 O1C O 0.74445(4) 0.25903(5) 0.17229(9) 0.01519(18) Uani 1 1 d . . . . .
 N1C N 0.78364(5) 0.25417(6) 0.40277(12) 0.0159(2) Uani 1 1 d . . . . .
 H1CA H 0.7708(8) 0.2389(10) 0.481(2) 0.023(5) Uiso 1 1 d . . . . .
 H1CB H 0.8199(8) 0.2583(10) 0.4226(19) 0.022(5) Uiso 1 1 d . . . . .
 C1C C 0.75833(6) 0.32527(7) 0.37122(14) 0.0198(3) Uani 1 1 d . . . . .
 H1CC H 0.787741 0.359451 0.346882 0.024 Uiso 1 1 calc R . . . .
 H1CD H 0.738365 0.343788 0.449807 0.024 Uiso 1 1 calc R . . . .
 C2C C 0.71726(6) 0.31089(7) 0.25049(14) 0.0177(2) Uani 1 1 d . . . . .
 H2CA H 0.680831 0.292979 0.281499 0.021 Uiso 1 1 calc R . . . .
 H2CB H 0.710110 0.354291 0.196298 0.021 Uiso 1 1 calc R . . . .
 C3C C 0.72061(6) 0.14801(7) 0.30566(14) 0.0178(2) Uani 1 1 d . . . . .
 C4C C 0.72757(7) 0.09647(7) 0.40646(15) 0.0223(3) Uani 1 1 d . . . . .
 C5C C 0.68782(8) 0.04417(8) 0.42873(19) 0.0330(4) Uani 1 1 d . . . . .
 H5C H 0.693678 0.010256 0.499244 0.040 Uiso 1 1 calc R . . . .
 C6C C 0.63987(8) 0.04385(9) 0.3443(2) 0.0367(4) Uani 1 1 d . . . . .
 C7C C 0.62925(7) 0.09267(9) 0.2430(2) 0.0336(4) Uani 1 1 d . . . . .
 H7C H 0.595365 0.091251 0.186868 0.040 Uiso 1 1 calc R . . . .
 C8C C 0.66990(6) 0.14422(8) 0.22549(17) 0.0241(3) Uani 1 1 d . . . . .
 H8C H 0.663048 0.178501 0.156041 0.029 Uiso 1 1 calc R . . . .
 C9C C 0.82261(6) 0.16806(7) 0.20249(13) 0.0156(2) Uani 1 1 d . . . . .
 C10C C 0.87392(6) 0.20027(7) 0.17681(14) 0.0180(3) Uani 1 1 d . . . . .
 C11C C 0.91719(6) 0.16837(9) 0.10829(15) 0.0243(3) Uani 1 1 d . . . . .
 H11C H 0.951691 0.192202 0.094308 0.029 Uiso 1 1 calc R . . . .
 C12C C 0.90768(6) 0.10073(9) 0.06177(16) 0.0264(3) Uani 1 1 d . . . . .
 C13C C 0.85882(7) 0.06446(8) 0.08245(16) 0.0249(3) Uani 1 1 d . . . . .
 H13C H 0.853425 0.017702 0.049652 0.030 Uiso 1 1 calc R . . . .
 C14C C 0.81740(6) 0.09866(7) 0.15330(15) 0.0198(3) Uani 1 1 d . . . . .
 H14C H 0.783646 0.073625 0.169333 0.024 Uiso 1 1 calc R . . . .
 B1C B 0.76824(6) 0.20546(8) 0.26771(15) 0.0141(3) Uani 1 1 d . . . . .

loop_
  _atom_site_aniso_label
  _atom_site_aniso_U_11
  _atom_site_aniso_U_22
  _atom_site_aniso_U_33
  _atom_site_aniso_U_23
  _atom_site_aniso_U_13
  _atom_site_aniso_U_12
 Cl1A 0.02633(17) 0.02918(18) 0.02131(17) -0.00846(14) 0.00570(13) 0.00111(13)
 Cl2A 0.02374(17) 0.02666(17) 0.02446(18) 0.00341(13) -0.00117(13)
 -0.00913(13)
 F1A 0.0392(6) 0.0303(5) 0.0576(7) 0.0022(5) -0.0067(5) -0.0197(4)
 F2A 0.0293(5) 0.0308(5) 0.0497(7) -0.0063(5) -0.0209(5) 0.0099(4)
 O1A 0.0175(4) 0.0190(4) 0.0107(4) -0.0002(3) 0.0016(3) 0.0019(3)
 N1A 0.0177(5) 0.0206(5) 0.0113(5) -0.0002(4) 0.0025(4) -0.0010(4)
 C1A 0.0267(7) 0.0206(6) 0.0173(6) 0.0034(5) 0.0030(5) 0.0027(5)
 C2A 0.0204(6) 0.0234(7) 0.0159(6) 0.0016(5) 0.0013(5) 0.0048(5)
 C3A 0.0161(6) 0.0189(6) 0.0135(6) 0.0006(5) -0.0011(5) -0.0007(5)
 C4A 0.0193(6) 0.0218(6) 0.0184(6) -0.0014(5) -0.0004(5) 0.0003(5)
 C5A 0.0317(8) 0.0215(7) 0.0270(8) -0.0037(6) -0.0058(6) -0.0028(6)
 C6A 0.0264(7) 0.0243(7) 0.0337(9) 0.0055(6) -0.0078(6) -0.0105(6)
 C7A 0.0184(7) 0.0308(8) 0.0295(8) 0.0076(6) 0.0007(6) -0.0049(6)
 C8A 0.0169(6) 0.0235(7) 0.0187(6) 0.0027(5) 0.0004(5) -0.0020(5)
 C9A 0.0135(5) 0.0207(6) 0.0107(5) -0.0024(5) 0.0028(4) -0.0005(4)
 C10A 0.0170(6) 0.0216(6) 0.0142(6) -0.0031(5) 0.0035(5) -0.0022(5)
 C11A 0.0158(6) 0.0279(7) 0.0216(7) -0.0073(6) -0.0006(5) -0.0006(5)
 C12A 0.0198(7) 0.0271(7) 0.0235(7) -0.0064(6) -0.0059(5) 0.0087(5)
 C13A 0.0226(7) 0.0202(6) 0.0229(7) -0.0027(5) -0.0015(5) 0.0054(5)
 C14A 0.0168(6) 0.0201(6) 0.0170(6) -0.0020(5) 0.0005(5) 0.0007(5)
 B1A 0.0147(6) 0.0185(6) 0.0097(6) 0.0002(5) 0.0016(5) -0.0008(5)
 Cl1B 0.0319(2) 0.0340(2) 0.02318(18) -0.00741(15) 0.00245(15) 0.00860(15)
 Cl2B 0.02179(16) 0.02639(17) 0.03109(19) 0.01325(15) -0.00461(14)
 -0.00710(13)
 F1B 0.0655(9) 0.0578(8) 0.0730(10) 0.0060(7) -0.0249(8) -0.0401(7)
 F2B 0.0254(5) 0.0297(5) 0.0408(6) 0.0132(4) -0.0132(4) 0.0009(4)
 O1B 0.0198(5) 0.0273(5) 0.0110(4) 0.0000(4) -0.0005(4) 0.0081(4)
 N1B 0.0185(5) 0.0206(5) 0.0118(5) 0.0004(4) -0.0006(4) 0.0006(4)
 C1B 0.0287(7) 0.0204(7) 0.0195(7) 0.0015(5) -0.0016(6) 0.0059(5)
 C2B 0.0237(7) 0.0270(7) 0.0155(6) -0.0012(5) -0.0032(5) 0.0095(5)
 C3B 0.0177(6) 0.0230(6) 0.0158(6) 0.0044(5) -0.0022(5) -0.0003(5)
 C4B 0.0254(7) 0.0214(7) 0.0196(7) 0.0024(5) -0.0044(5) -0.0004(5)
 C5B 0.0473(10) 0.0217(7) 0.0291(8) 0.0029(6) -0.0117(7) -0.0055(7)
 C6B 0.0400(10) 0.0352(9) 0.0420(10) 0.0121(8) -0.0193(8) -0.0199(8)
 C7B 0.0231(8) 0.0490(11) 0.0403(10) 0.0158(9) -0.0073(7) -0.0130(7)
 C8B 0.0193(7) 0.0376(9) 0.0255(8) 0.0083(7) -0.0011(6) -0.0042(6)
 C9B 0.0150(6) 0.0174(6) 0.0118(5) -0.0003(4) 0.0017(4) 0.0006(4)
 C10B 0.0166(6) 0.0173(6) 0.0156(6) 0.0027(5) 0.0030(5) 0.0000(4)
 C11B 0.0151(6) 0.0225(7) 0.0207(6) 0.0016(5) -0.0012(5) -0.0003(5)
 C12B 0.0181(6) 0.0213(6) 0.0207(7) 0.0027(5) -0.0038(5) 0.0048(5)
 C13B 0.0224(7) 0.0165(6) 0.0230(7) 0.0029(5) -0.0024(5) 0.0009(5)
 C14B 0.0167(6) 0.0173(6) 0.0205(6) 0.0008(5) -0.0007(5) -0.0014(5)
 B1B 0.0148(6) 0.0203(7) 0.0114(6) 0.0013(5) 0.0006(5) 0.0011(5)
 Cl1C 0.0428(2) 0.02220(16) 0.01723(16) 0.00264(13) 0.00321(14) 0.01098(15)
 Cl2C 0.02122(16) 0.02757(18) 0.03056(19) -0.00560(14) 0.00778(14)
 -0.00618(13)
 F1C 0.0470(7) 0.0318(6) 0.0983(11) -0.0035(6) 0.0378(7) -0.0195(5)
 F2C 0.0277(5) 0.0516(7) 0.0452(6) -0.0210(5) 0.0164(5) 0.0048(5)
 O1C 0.0173(4) 0.0181(4) 0.0103(4) 0.0004(3) 0.0017(3) 0.0016(3)
 N1C 0.0170(5) 0.0199(5) 0.0110(5) 0.0003(4) 0.0013(4) 0.0011(4)
 C1C 0.0248(7) 0.0179(6) 0.0167(6) -0.0020(5) 0.0016(5) 0.0023(5)
 C2C 0.0184(6) 0.0194(6) 0.0156(6) 0.0007(5) 0.0027(5) 0.0036(5)
 C3C 0.0193(6) 0.0168(6) 0.0180(6) -0.0012(5) 0.0077(5) 0.0002(5)
 C4C 0.0291(7) 0.0176(6) 0.0213(7) 0.0001(5) 0.0115(6) 0.0034(5)
 C5C 0.0455(10) 0.0170(7) 0.0390(9) 0.0037(6) 0.0265(8) 0.0012(6)
 C6C 0.0317(9) 0.0215(7) 0.0594(12) -0.0056(7) 0.0276(8) -0.0093(6)
 C7C 0.0189(7) 0.0296(8) 0.0533(11) -0.0087(8) 0.0100(7) -0.0067(6)
 C8C 0.0194(6) 0.0226(7) 0.0306(8) -0.0021(6) 0.0057(6) -0.0025(5)
 C9C 0.0161(6) 0.0204(6) 0.0105(5) 0.0011(5) 0.0008(4) 0.0018(5)
 C10C 0.0170(6) 0.0233(6) 0.0139(6) -0.0008(5) 0.0013(5) 0.0006(5)
 C11C 0.0172(6) 0.0359(8) 0.0203(7) -0.0025(6) 0.0049(5) 0.0001(6)
 C12C 0.0213(7) 0.0369(8) 0.0216(7) -0.0074(6) 0.0060(6) 0.0079(6)
 C13C 0.0263(7) 0.0256(7) 0.0230(7) -0.0068(6) 0.0044(6) 0.0039(6)
 C14C 0.0213(6) 0.0208(6) 0.0175(6) -0.0008(5) 0.0031(5) 0.0018(5)
 B1C 0.0151(6) 0.0168(6) 0.0106(6) -0.0002(5) 0.0019(5) -0.0003(5)

_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
 Cl1A C4A 1.7583(15) . ?
 Cl2A C10A 1.7543(15) . ?
 F1A C6A 1.3583(17) . ?
 F2A C12A 1.3576(17) . ?
 O1A C2A 1.4172(16) . ?
 O1A B1A 1.4756(17) . ?
 N1A C1A 1.4975(18) . ?
 N1A B1A 1.6368(18) . ?
 C1A C2A 1.512(2) . ?
 C3A C4A 1.3950(19) . ?
 C3A C8A 1.4047(19) . ?
 C3A B1A 1.627(2) . ?
 C4A C5A 1.391(2) . ?
 C5A C6A 1.378(2) . ?
 C6A C7A 1.370(2) . ?
 C7A C8A 1.394(2) . ?
 C9A C10A 1.4021(18) . ?
 C9A C14A 1.4029(19) . ?
 C9A B1A 1.630(2) . ?
 C10A C11A 1.392(2) . ?
 C11A C12A 1.377(2) . ?
 C12A C13A 1.373(2) . ?
 C13A C14A 1.392(2) . ?
 Cl1B C4B 1.7608(16) . ?
 Cl2B C10B 1.7613(13) . ?
 F1B C6B 1.362(2) . ?
 F2B C12B 1.3595(16) . ?
 O1B C2B 1.4208(17) . ?
 O1B B1B 1.4757(18) . ?
 N1B C1B 1.5001(18) . ?
 N1B B1B 1.6429(19) . ?
 C1B C2B 1.520(2) . ?
 C3B C4B 1.390(2) . ?
 C3B C8B 1.405(2) . ?
 C3B B1B 1.634(2) . ?
 C4B C5B 1.394(2) . ?
 C5B C6B 1.374(3) . ?
 C6B C7B 1.365(3) . ?
 C7B C8B 1.387(2) . ?
 C9B C10B 1.3990(18) . ?
 C9B C14B 1.4008(18) . ?
 C9B B1B 1.624(2) . ?
 C10B C11B 1.3908(19) . ?
 C11B C12B 1.376(2) . ?
 C12B C13B 1.369(2) . ?
 C13B C14B 1.392(2) . ?
 Cl1C C4C 1.7591(17) . ?
 Cl2C C10C 1.7625(15) . ?
 F1C C6C 1.3577(18) . ?
 F2C C12C 1.3597(17) . ?
 O1C C2C 1.4225(16) . ?
 O1C B1C 1.4741(17) . ?
 N1C C1C 1.5018(18) . ?
 N1C B1C 1.6417(19) . ?
 C1C C2C 1.518(2) . ?
 C3C C4C 1.395(2) . ?
 C3C C8C 1.403(2) . ?
 C3C B1C 1.626(2) . ?
 C4C C5C 1.393(2) . ?
 C5C C6C 1.371(3) . ?
 C6C C7C 1.373(3) . ?
 C7C C8C 1.389(2) . ?
 C9C C10C 1.3949(19) . ?
 C9C C14C 1.4057(19) . ?
 C9C B1C 1.6301(19) . ?
 C10C C11C 1.3933(19) . ?
 C11C C12C 1.377(2) . ?
 C12C C13C 1.370(2) . ?
 C13C C14C 1.392(2) . ?

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
 C2A O1A B1A 108.56(10) . . ?
 C1A N1A B1A 105.95(10) . . ?
 N1A C1A C2A 104.00(11) . . ?
 O1A C2A C1A 105.50(11) . . ?
 C4A C3A C8A 114.92(13) . . ?
 C4A C3A B1A 125.09(12) . . ?
 C8A C3A B1A 119.81(12) . . ?
 C3A C4A Cl1A 119.52(11) . . ?
 C5A C4A Cl1A 116.24(12) . . ?
 C5A C4A C3A 124.22(14) . . ?
 C6A C5A C4A 116.86(15) . . ?
 F1A C6A C5A 117.47(16) . . ?
 F1A C6A C7A 119.41(15) . . ?
 C7A C6A C5A 123.12(14) . . ?
 C6A C7A C8A 117.71(14) . . ?
 C7A C8A C3A 123.15(14) . . ?
 C10A C9A C14A 114.24(12) . . ?
 C10A C9A B1A 125.78(12) . . ?
 C14A C9A B1A 119.66(11) . . ?
 C9A C10A Cl2A 121.40(11) . . ?
 C11A C10A Cl2A 114.44(11) . . ?
 C11A C10A C9A 124.16(13) . . ?
 C12A C11A C10A 117.47(13) . . ?
 F2A C12A C11A 118.65(14) . . ?
 F2A C12A C13A 118.91(14) . . ?
 C13A C12A C11A 122.44(14) . . ?
 C12A C13A C14A 117.85(14) . . ?
 C13A C14A C9A 123.82(13) . . ?
 O1A B1A N1A 100.79(10) . . ?
 O1A B1A C3A 111.44(11) . . ?
 O1A B1A C9A 109.35(11) . . ?
 C3A B1A N1A 108.93(10) . . ?
 C3A B1A C9A 112.41(11) . . ?
 C9A B1A N1A 113.37(10) . . ?
 C2B O1B B1B 108.48(10) . . ?
 C1B N1B B1B 105.68(10) . . ?
 N1B C1B C2B 103.60(12) . . ?
 O1B C2B C1B 104.88(11) . . ?
 C4B C3B C8B 114.65(14) . . ?
 C4B C3B B1B 125.46(12) . . ?
 C8B C3B B1B 119.88(13) . . ?
 C3B C4B Cl1B 119.35(11) . . ?
 C3B C4B C5B 124.07(15) . . ?
 C5B C4B Cl1B 116.59(13) . . ?
 C6B C5B C4B 117.15(17) . . ?
 F1B C6B C5B 118.1(2) . . ?
 F1B C6B C7B 119.12(19) . . ?
 C7B C6B C5B 122.77(16) . . ?
 C6B C7B C8B 117.96(17) . . ?
 C7B C8B C3B 123.39(17) . . ?
 C10B C9B C14B 114.11(12) . . ?
 C10B C9B B1B 128.50(12) . . ?
 C14B C9B B1B 116.68(11) . . ?
 C9B C10B Cl2B 121.85(10) . . ?
 C11B C10B Cl2B 113.99(10) . . ?
 C11B C10B C9B 124.16(12) . . ?
 C12B C11B C10B 117.47(13) . . ?
 F2B C12B C11B 118.52(13) . . ?
 F2B C12B C13B 118.94(13) . . ?
 C13B C12B C11B 122.54(13) . . ?
 C12B C13B C14B 117.59(13) . . ?
 C13B C14B C9B 124.07(13) . . ?
 O1B B1B N1B 100.92(10) . . ?
 O1B B1B C3B 111.61(11) . . ?
 O1B B1B C9B 107.51(11) . . ?
 C3B B1B N1B 106.49(11) . . ?
 C9B B1B N1B 115.78(11) . . ?
 C9B B1B C3B 113.84(11) . . ?
 C2C O1C B1C 107.62(10) . . ?
 C1C N1C B1C 105.63(10) . . ?
 N1C C1C C2C 103.43(11) . . ?
 O1C C2C C1C 104.82(11) . . ?
 C4C C3C C8C 115.36(13) . . ?
 C4C C3C B1C 125.07(13) . . ?
 C8C C3C B1C 119.32(12) . . ?
 C3C C4C Cl1C 119.66(11) . . ?
 C5C C4C Cl1C 116.62(13) . . ?
 C5C C4C C3C 123.69(16) . . ?
 C6C C5C C4C 117.00(16) . . ?
 F1C C6C C5C 118.17(18) . . ?
 F1C C6C C7C 118.47(19) . . ?
 C5C C6C C7C 123.36(15) . . ?
 C6C C7C C8C 117.54(17) . . ?
 C7C C8C C3C 123.04(16) . . ?
 C10C C9C C14C 114.20(12) . . ?
 C10C C9C B1C 126.43(12) . . ?
 C14C C9C B1C 119.05(12) . . ?
 C9C C10C Cl2C 121.04(10) . . ?
 C11C C10C Cl2C 114.43(11) . . ?
 C11C C10C C9C 124.52(13) . . ?
 C12C C11C C10C 116.95(14) . . ?
 F2C C12C C11C 118.33(14) . . ?
 F2C C12C C13C 118.73(14) . . ?
 C13C C12C C11C 122.94(14) . . ?
 C12C C13C C14C 117.54(14) . . ?
 C13C C14C C9C 123.82(14) . . ?
 O1C B1C N1C 100.76(10) . . ?
 O1C B1C C3C 111.16(11) . . ?
 O1C B1C C9C 109.51(10) . . ?
 C3C B1C N1C 108.67(10) . . ?
 C3C B1C C9C 111.72(11) . . ?
 C9C B1C N1C 114.54(11) . . ?

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
 N1A H1AA Cl2A 0.864(19) 2.633(19) 3.1483(13) 119.4(15) .
 N1A H1AB Cl1A 0.86(2) 2.86(2) 3.2630(13) 110.8(16) .
 N1A H1AB O1A 0.86(2) 2.04(2) 2.8460(15) 155.8(19) 4_565
 N1B H1BA Cl2B 0.89(2) 2.50(2) 3.1108(13) 126.5(17) .
 N1B H1BB Cl1B 0.92(2) 2.93(2) 3.3202(13) 106.9(15) .
 N1B H1BB O1B 0.92(2) 2.00(2) 2.8690(15) 157(2) 4_565
 N1C H1CA Cl1C 0.89(2) 2.802(19) 3.2196(12) 110.4(14) .
 N1C H1CA O1C 0.89(2) 2.01(2) 2.8602(15) 159.5(17) 4_566
 N1C H1CB Cl2C 0.874(19) 2.618(19) 3.1444(12) 119.7(15) .

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'

#===END
