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_4b_15srv104 
_database_code_depnum_ccdc_archive	1551615     

_audit_creation_date              2015-04-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;

_chemical_name_common             ?
_chemical_name_systematic         
; Bis-3,4,5-trifluorophenylborinic acid ethylenediamine complex 
;
_chemical_formula_moiety          'C14 H13 B F6 N2 O,0.5(C D Cl3)'
_chemical_formula_sum             'C14.5 H13 B Cl1.5 D0.5 F6 N2 O'
_chemical_formula_weight          410.26
_chemical_absolute_configuration  ?
_chemical_melting_point           363.7(2.5)
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'
 'D' 'D' 0.0000 0.0000 '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            7
_space_group_name_H-M_alt         'P 1 c 1'
_space_group_name_Hall            'P -2yc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 'x, -y, z+1/2'

_cell_length_a                    11.7500(5)
_cell_length_b                    11.0269(4)
_cell_length_c                    13.1973(5)
_cell_angle_alpha                 90
_cell_angle_beta                  97.3307(14)
_cell_angle_gamma                 90
_cell_volume                      1695.95(11)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     9967
_cell_measurement_temperature     120
_cell_measurement_theta_max       29.27
_cell_measurement_theta_min       2.42
_shelx_estimated_absorpt_T_max    0.905
_shelx_estimated_absorpt_T_min    0.841
_exptl_absorpt_coefficient_mu     0.373
_exptl_absorpt_correction_T_max   1.0000
_exptl_absorpt_correction_T_min   0.9440
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1159 before and 0.0452 after correction.
The Ratio of minimum to maximum transmission is 0.9440.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             colourless
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.607
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        block
_exptl_crystal_F_000              828
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 2.00 2.00 -1.00 0.1490
 -1.00 0.00 2.00 0.1030
 1.00 1.00 -2.00 0.1510
 -1.00 1.00 1.00 0.1680
 0.00 2.00 -1.00 0.2330
 3.00 0.00 -2.00 0.1620
 -1.00 -1.00 2.00 0.1290
 -2.00 -1.00 3.00 0.1060
 -1.00 2.00 -1.00 0.2440
 -1.00 0.00 1.00 0.1110
 -3.00 2.00 1.00 0.1900
 3.00 -1.00 -2.00 0.1730
 0.00 -1.00 1.00 0.1680
 1.00 -2.00 -3.00 0.1020
 0.00 -3.00 -1.00 0.1310
 0.00 3.00 1.00 0.1930
 -3.00 1.00 -2.00 0.2180
 0.00 1.00 -2.00 0.1800
 3.00 1.00 -1.00 0.1800
 0.00 -1.00 3.00 0.1850
 -3.00 -1.00 1.00 0.1800
 0.00 1.00 -3.00 0.1700
 -1.00 0.00 -3.00 0.1520
 3.00 1.00 3.00 0.2200
 1.00 2.00 3.00 0.1370
 0.00 -2.00 -3.00 0.0840

_exptl_crystal_size_max           0.481
_exptl_crystal_size_mid           0.336
_exptl_crystal_size_min           0.274
_exptl_special_details
;
 Data were collected in shutterless mode. Full sphere of reciprocal 
space was nominally covered by 4 runs of narrow-frame ω-scans (scan 
width 0.5°, 10s exposure), every run at a different φ angle.
One run of φ-scans (scan width 1°, 1s exposure) was used for 
scaling overflowing intensities. Crystal to detector distance 3.50 cm.
;
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_exptl_twin_twinlaw_details       '-1 0 0 0 -1 0 0 0 -1'
_diffrn_reflns_av_R_equivalents   0.0288
_diffrn_reflns_av_unetI/netI      0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max        16
_diffrn_reflns_limit_h_min        -16
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_number             35272
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full         25.242
_diffrn_reflns_theta_max          29.325
_diffrn_reflns_theta_min          2.415
_diffrn_ambient_temperature       120
_diffrn_detector_area_resol_mean  ?
_diffrn_detector_type             'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device        '3-circle area detector 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                    'ImuS microsource'
_diffrn_standards_number          0
_reflns_Friedel_coverage          0.997
_reflns_Friedel_fraction_full     1.000
_reflns_Friedel_fraction_max      0.998
_reflns_number_gt                 8294
_reflns_number_total              9254
_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 v8.34A (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   'SHELXL 2014/7 multi-CPU version (Sheldrick, 2008)'
_computing_structure_solution     'SHELXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max          0.501
_refine_diff_density_min          -0.634
_refine_diff_density_rms          0.064
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack    0.39(10)
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.019
_refine_ls_hydrogen_treatment     mixed
_refine_ls_matrix_type            full
_refine_ls_number_parameters      553
_refine_ls_number_reflns          9254
_refine_ls_number_restraints      57
_refine_ls_R_factor_all           0.0535
_refine_ls_R_factor_gt            0.0459
_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
'w=1/[σ²(Fo²)+(0.0770P)²+0.7700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1211
_refine_ls_wR_factor_ref          0.1267
_refine_special_details
;
 Refined as a 2-component inversion twin, BASF = 0.39(10). 
The CDCl₃ molecule is disordered. The minor orientation (15%) 
comprises C(2S), D(2), Cl(6), Cl(7) and Cl(8). The major 
orientation includes C(1S) with D(1) and Cl(1) (85%), while 
two other Cl atoms are further disordered: Cl(2) and Cl(3) have 
occupancies of 70%, Cl(4) and Cl(5) of 15%. 
One trifluorophenyl group at B(1) shows a flipping disorder: 
C(4), C(5), C(6), F(2) and F(3) are disordered between positions 
A and B with occupancies refined to 57.8(8) and 42.2(8)%, 
respectively. Hydroxyl and amino H atoms - refall, other H atoms 
- riding model (constr).
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.61(10) 0.39(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
3. Restrained distances
 C6A-C1 \\sim C6B-C1
 with sigma of 0.02
 C4A-C3 \\sim C4B-C3
 with sigma of 0.02
 F2A-C4A \\sim F2B-C4B
 with sigma of 0.02
 Cl4-C1S \\sim Cl2-C1S \\sim Cl3-C1S \\sim Cl5-C1S \\sim Cl1-C1S \\sim Cl8-C2S
\\sim Cl6-C2S \\sim Cl7-C2S
 with sigma of 0.02
 C6A-C5A \\sim C6B-C5B
 with sigma of 0.02
 C5A-C4A \\sim C5B-C4B
 with sigma of 0.02
 F3A-C5A \\sim F3B-C5B
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uiso(C6A) = Uiso(C6B)
Uiso(C4B) = Uiso(C4A)
Uanis(F2A) = Uanis(F2B)
Uanis(F3A) = Uanis(F3B)
Uanis(C2S) = Uanis(C1S)
Uanis(C5B) = Uanis(C5A)
5. Rigid body (RIGU) restrains
 F1, C1, C2, C3, F2A, F3A, C4A, C5A, C6A, F2B, F3B, C4B, C5B, C6B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(F2B)=Sof(F3B)=Sof(C4B)=Sof(C5B)=Sof(C6B)=Sof(H6B)=1-FVAR(1)
 Sof(F2A)=Sof(F3A)=Sof(C4A)=Sof(C5A)=Sof(C6A)=Sof(H6A)=FVAR(1)
 Fixed Sof: Cl6(0.15) Cl7(0.15) Cl8(0.15) C2S(0.15) D2(0.15) C1S(0.85)
 D1(0.85) Cl1(0.85) Cl2(0.7) Cl3(0.7) Cl4(0.15) Cl5(0.15)
7.a Riding coordinates:
 C2S(D2), C1S(D1), C6A(H6A), C6B(H6B)
7.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C7(H7A,H7B), C8(H8A,H8B)
7.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C22(H22), C26(H26), C2(H2), C10(H10), C14(H14)
;
_atom_sites_solution_hydrogens    mixed
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    ?
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
 Cl6 Cl -0.0838(10) 0.3964(11) 0.2501(10) 0.047(2) Uiso 0.15 1 d D . P A 3
 Cl7 Cl -0.1780(9) 0.1702(8) 0.2722(19) 0.125(8) Uani 0.15 1 d D . P A 3
 Cl8 Cl 0.0435(11) 0.2473(9) 0.4143(7) 0.072(3) Uani 0.15 1 d D . P A 3
 C2S C -0.0476(19) 0.2452(19) 0.2934(19) 0.0496(13) Uani 0.15 1 d D . P A 3
 D2 D -0.0006 0.2119 0.2419 0.060 Uiso 0.15 1 d R . P A 3
 C1S C -0.0483(5) 0.2880(5) 0.3630(5) 0.0496(13) Uani 0.85 1 d D . P . .
 D1 D -0.0159 0.3330 0.4260 0.060 Uiso 0.85 1 d R . P B 1
 Cl1 Cl -0.0429(3) 0.3716(3) 0.2527(2) 0.1037(12) Uani 0.85 1 d D . P C 1
 Cl2 Cl -0.1936(2) 0.2955(3) 0.3911(3) 0.0831(8) Uani 0.7 1 d D . P C 1
 Cl3 Cl -0.0052(2) 0.14034(18) 0.36495(18) 0.0681(6) Uani 0.7 1 d D . P C 1
 Cl4 Cl -0.1688(6) 0.2074(8) 0.3790(7) 0.0441(17) Uani 0.15 1 d D . P C 2
 Cl5 Cl 0.0525(9) 0.1727(9) 0.3203(8) 0.057(2) Uiso 0.15 1 d D . P C 2
 F7 F 0.5340(2) 1.16908(17) 0.17500(15) 0.0316(5) Uani 1 1 d . . . . .
 F8 F 0.5406(2) 1.29059(16) 0.35434(16) 0.0291(5) Uani 1 1 d . . . . .
 F9 F 0.58267(19) 1.16952(18) 0.53195(14) 0.0252(4) Uani 1 1 d . . . . .
 F10 F 1.03479(18) 0.8811(3) 0.40980(19) 0.0415(6) Uani 1 1 d . . . . .
 F11 F 1.0960(2) 0.6671(3) 0.4957(2) 0.0522(8) Uani 1 1 d . . . . .
 F12 F 0.9341(2) 0.5006(3) 0.5237(2) 0.0475(7) Uani 1 1 d . . . . .
 O2 O 0.53378(18) 0.71442(19) 0.41693(16) 0.0140(4) Uani 1 1 d . . . . .
 H2C H 0.559(4) 0.675(4) 0.461(3) 0.017 Uiso 1 1 d R . . . .
 N3 N 0.5932(2) 0.7190(2) 0.24470(18) 0.0106(4) Uani 1 1 d . . . . .
 H3A H 0.526(3) 0.743(3) 0.215(2) 0.002(7) Uiso 1 1 d . . . . .
 H3B H 0.655(4) 0.764(4) 0.202(4) 0.035(12) Uiso 1 1 d . . . . .
 N4 N 0.5924(3) 0.4148(2) 0.1078(2) 0.0196(5) Uani 1 1 d . . . . .
 H4A H 0.662(4) 0.394(4) 0.138(4) 0.027(11) Uiso 1 1 d . . . . .
 H4B H 0.545(5) 0.379(5) 0.135(5) 0.051(16) Uiso 1 1 d . . . . .
 C15 C 0.5969(2) 0.9178(2) 0.3535(2) 0.0114(5) Uani 1 1 d . . . . .
 C16 C 0.5747(3) 0.9830(3) 0.2620(2) 0.0159(5) Uani 1 1 d . . . . .
 H16 H 0.5723 0.9420 0.1984 0.019 Uiso 1 1 calc R . . . .
 C17 C 0.5562(3) 1.1067(3) 0.2639(2) 0.0187(6) Uani 1 1 d . . . . .
 C18 C 0.5587(3) 1.1697(3) 0.3536(2) 0.0185(6) Uani 1 1 d . . . . .
 C19 C 0.5814(3) 1.1061(3) 0.4438(2) 0.0161(6) Uani 1 1 d . . . . .
 C20 C 0.6003(2) 0.9826(3) 0.4450(2) 0.0135(5) Uani 1 1 d . . . . .
 H20 H 0.6159 0.9412 0.5084 0.016 Uiso 1 1 calc R . . . .
 C21 C 0.7516(2) 0.7423(3) 0.4037(2) 0.0135(5) Uani 1 1 d . . . . .
 C22 C 0.8379(3) 0.8271(3) 0.3914(2) 0.0189(6) Uani 1 1 d . . . . .
 H22 H 0.8180 0.9038 0.3616 0.023 Uiso 1 1 calc R . . . .
 C23 C 0.9520(3) 0.7993(4) 0.4227(3) 0.0269(7) Uani 1 1 d . . . . .
 C24 C 0.9842(3) 0.6912(4) 0.4665(3) 0.0335(9) Uani 1 1 d . . . . .
 C25 C 0.9010(3) 0.6081(4) 0.4799(3) 0.0303(8) Uani 1 1 d . . . . .
 C26 C 0.7857(3) 0.6312(3) 0.4489(2) 0.0201(6) Uani 1 1 d . . . . .
 H26 H 0.7298 0.5714 0.4584 0.024 Uiso 1 1 calc R . . . .
 C27 C 0.6018(3) 0.5851(2) 0.2334(2) 0.0141(5) Uani 1 1 d . . . . .
 H27A H 0.5421 0.5455 0.2685 0.017 Uiso 1 1 calc R . . . .
 H27B H 0.6777 0.5575 0.2668 0.017 Uiso 1 1 calc R . . . .
 C28 C 0.5870(3) 0.5466(3) 0.1211(2) 0.0150(5) Uani 1 1 d . . . . .
 H28A H 0.5121 0.5765 0.0875 0.018 Uiso 1 1 calc R . . . .
 H28B H 0.6479 0.5851 0.0867 0.018 Uiso 1 1 calc R . . . .
 B2 B 0.6181(3) 0.7717(3) 0.3612(2) 0.0104(5) Uani 1 1 d . . . . .
 F1 F 0.31953(18) 0.33589(18) 0.07665(15) 0.0251(4) Uani 1 1 d . U . . .
 F4 F -0.15455(18) 0.6673(3) 0.1763(2) 0.0440(7) Uani 1 1 d . . . . .
 F5 F -0.1925(2) 0.8987(3) 0.1178(2) 0.0524(8) Uani 1 1 d . . . . .
 F6 F -0.0124(2) 1.0521(2) 0.11094(19) 0.0447(7) Uani 1 1 d . . . . .
 O1 O 0.35998(17) 0.78212(18) 0.19034(16) 0.0131(4) Uani 1 1 d . . . . .
 H1 H 0.336(4) 0.830(4) 0.134(4) 0.032(11) Uiso 1 1 d . . . . .
 N1 N 0.2996(2) 0.7820(2) 0.36277(18) 0.0109(4) Uani 1 1 d . . . . .
 H1A H 0.370(4) 0.756(4) 0.383(4) 0.027(11) Uiso 1 1 d . . . . .
 H1B H 0.253(3) 0.752(3) 0.398(3) 0.008(8) Uiso 1 1 d . . . . .
 N2 N 0.3080(2) 1.0815(2) 0.5058(2) 0.0185(5) Uani 1 1 d . . . . .
 H2A H 0.363(3) 1.123(4) 0.475(3) 0.016(9) Uiso 1 1 d . . . . .
 H2B H 0.226(4) 1.114(4) 0.478(4) 0.033(12) Uiso 1 1 d . . . . .
 C1 C 0.2792(2) 0.5853(2) 0.2511(2) 0.0128(5) Uani 1 1 d D U . . .
 C2 C 0.2945(2) 0.5210(3) 0.1619(2) 0.0151(5) Uani 1 1 d . U . . .
 H2 H 0.3006 0.5642 0.1005 0.018 Uiso 1 1 calc R . . . .
 C3 C 0.3008(3) 0.3968(3) 0.1621(2) 0.0161(5) Uani 1 1 d D U . . .
 C7 C 0.2956(2) 0.9151(2) 0.3781(2) 0.0116(5) Uani 1 1 d . . . . .
 H7A H 0.2199 0.9460 0.3472 0.014 Uiso 1 1 calc R . . . .
 H7B H 0.3551 0.9541 0.3423 0.014 Uiso 1 1 calc R . . . .
 C8 C 0.3148(3) 0.9501(2) 0.4904(2) 0.0142(5) Uani 1 1 d . . . . .
 H8A H 0.2565 0.9094 0.5264 0.017 Uiso 1 1 calc R . . . .
 H8B H 0.3913 0.9209 0.5208 0.017 Uiso 1 1 calc R . . . .
 C9 C 0.1412(2) 0.7765(3) 0.2021(2) 0.0139(5) Uani 1 1 d . . . . .
 C10 C 0.0468(3) 0.6997(3) 0.2025(2) 0.0201(6) Uani 1 1 d . . . . .
 H10 H 0.0583 0.6177 0.2232 0.024 Uiso 1 1 calc R . . . .
 C11 C -0.0633(3) 0.7419(4) 0.1731(3) 0.0287(8) Uani 1 1 d . . . . .
 C12 C -0.0842(3) 0.8592(4) 0.1434(3) 0.0327(9) Uani 1 1 d . . . . .
 C13 C 0.0080(3) 0.9355(4) 0.1401(3) 0.0286(8) Uani 1 1 d . . . . .
 C14 C 0.1191(3) 0.8964(3) 0.1680(2) 0.0185(6) Uani 1 1 d . . . . .
 H14 H 0.1813 0.9506 0.1642 0.022 Uiso 1 1 calc R . . . .
 B1 B 0.2710(3) 0.7326(3) 0.2447(2) 0.0114(5) Uani 1 1 d . . . . .
 F2A F 0.2868(19) 0.2065(11) 0.249(3) 0.031(3) Uani 0.578(8) 1 d D U P D 1
 F3A F 0.2424(7) 0.3258(5) 0.4175(4) 0.0411(14) Uani 0.578(8) 1 d D U P D 1
 C4A C 0.2808(5) 0.3288(6) 0.2467(5) 0.0166(8) Uiso 0.578(8) 1 d D U P D 1
 C5A C 0.2613(9) 0.3912(9) 0.3339(8) 0.023(2) Uani 0.578(8) 1 d D U P D 1
 C6A C 0.2567(5) 0.5163(5) 0.3358(4) 0.0135(8) Uiso 0.578(8) 1 d D U P D 1
 H6A H 0.2370 0.5563 0.3949 0.016 Uiso 0.578(8) 1 d R . P D 1
 F2B F 0.312(3) 0.2100(16) 0.246(4) 0.031(3) Uani 0.422(8) 1 d D U P D 2
 F3B F 0.3051(10) 0.3288(7) 0.4264(6) 0.0411(14) Uani 0.422(8) 1 d D U P D 2
 C4B C 0.3063(8) 0.3318(8) 0.2494(7) 0.0166(8) Uiso 0.422(8) 1 d D U P D 2
 C5B C 0.2975(14) 0.3943(12) 0.3380(11) 0.023(2) Uani 0.422(8) 1 d D U P D 2
 C6B C 0.2917(8) 0.5178(7) 0.3424(6) 0.0135(8) Uiso 0.422(8) 1 d D U P D 2
 H6B H 0.2916 0.5580 0.4061 0.016 Uiso 0.422(8) 1 d R . P D 2


_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
 Cl6 C2S 1.796(19) . ?
 Cl7 C2S 1.732(18) . ?
 Cl8 C2S 1.805(18) . ?
 C1S Cl1 1.731(6) . ?
 C1S Cl2 1.795(6) . ?
 C1S Cl3 1.704(6) . ?
 C1S Cl4 1.708(8) . ?
 C1S Cl5 1.873(10) . ?
 F7 C17 1.356(3) . ?
 F8 C18 1.351(3) . ?
 F9 C19 1.356(3) . ?
 F10 C23 1.354(4) . ?
 F11 C24 1.347(4) . ?
 F12 C25 1.354(4) . ?
 O2 B2 1.451(4) . ?
 N3 C27 1.489(3) . ?
 N3 B2 1.635(4) . ?
 N4 C28 1.466(4) . ?
 C15 C16 1.402(4) . ?
 C15 C20 1.398(4) . ?
 C15 B2 1.631(4) . ?
 C16 C17 1.382(4) . ?
 C17 C18 1.370(4) . ?
 C18 C19 1.378(4) . ?
 C19 C20 1.379(4) . ?
 C21 C22 1.404(4) . ?
 C21 C26 1.398(4) . ?
 C21 B2 1.630(4) . ?
 C22 C23 1.386(5) . ?
 C23 C24 1.357(6) . ?
 C24 C25 1.369(6) . ?
 C25 C26 1.388(4) . ?
 C27 C28 1.531(4) . ?
 F1 C3 1.355(3) . ?
 F4 C11 1.356(4) . ?
 F5 C12 1.347(4) . ?
 F6 C13 1.354(4) . ?
 O1 B1 1.447(4) . ?
 N1 C7 1.483(3) . ?
 N1 B1 1.645(4) . ?
 N2 C8 1.467(4) . ?
 C1 C2 1.406(4) . ?
 C1 B1 1.629(4) . ?
 C1 C6A 1.404(6) . ?
 C1 C6B 1.408(8) . ?
 C2 C3 1.371(4) . ?
 C3 C4A 1.389(7) . ?
 C3 C4B 1.351(9) . ?
 C7 C8 1.521(4) . ?
 C9 C10 1.396(4) . ?
 C9 C14 1.410(4) . ?
 C9 B1 1.630(4) . ?
 C10 C11 1.383(5) . ?
 C11 C12 1.365(6) . ?
 C12 C13 1.376(6) . ?
 C13 C14 1.380(4) . ?
 F2A C4A 1.351(12) . ?
 F3A C5A 1.360(9) . ?
 C4A C5A 1.385(10) . ?
 C5A C6A 1.381(10) . ?
 F2B C4B 1.345(17) . ?
 F3B C5B 1.365(14) . ?
 C4B C5B 1.373(15) . ?
 C5B C6B 1.364(14) . ?

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
 Cl6 C2S Cl8 111.1(12) . . ?
 Cl7 C2S Cl6 102.9(12) . . ?
 Cl7 C2S Cl8 124.1(17) . . ?
 Cl1 C1S Cl2 106.7(4) . . ?
 Cl3 C1S Cl1 118.6(4) . . ?
 Cl3 C1S Cl2 109.2(3) . . ?
 Cl4 C1S Cl5 104.5(5) . . ?
 C27 N3 B2 116.1(2) . . ?
 C16 C15 B2 124.8(2) . . ?
 C20 C15 C16 117.6(2) . . ?
 C20 C15 B2 117.6(2) . . ?
 C17 C16 C15 120.2(3) . . ?
 F7 C17 C16 119.9(3) . . ?
 F7 C17 C18 118.1(3) . . ?
 C18 C17 C16 122.0(3) . . ?
 F8 C18 C17 121.4(3) . . ?
 F8 C18 C19 120.7(3) . . ?
 C17 C18 C19 118.0(3) . . ?
 F9 C19 C18 117.3(3) . . ?
 F9 C19 C20 121.0(3) . . ?
 C18 C19 C20 121.7(3) . . ?
 C19 C20 C15 120.5(3) . . ?
 C22 C21 B2 120.4(3) . . ?
 C26 C21 C22 117.5(3) . . ?
 C26 C21 B2 122.1(3) . . ?
 C23 C22 C21 120.3(3) . . ?
 F10 C23 C22 119.9(4) . . ?
 F10 C23 C24 118.2(3) . . ?
 C24 C23 C22 121.9(3) . . ?
 F11 C24 C23 120.3(4) . . ?
 F11 C24 C25 121.1(4) . . ?
 C23 C24 C25 118.5(3) . . ?
 F12 C25 C24 118.1(3) . . ?
 F12 C25 C26 120.2(4) . . ?
 C24 C25 C26 121.7(3) . . ?
 C25 C26 C21 120.1(3) . . ?
 N3 C27 C28 111.8(2) . . ?
 N4 C28 C27 112.9(2) . . ?
 O2 B2 N3 105.7(2) . . ?
 O2 B2 C15 110.6(2) . . ?
 O2 B2 C21 115.4(2) . . ?
 C15 B2 N3 106.5(2) . . ?
 C21 B2 N3 107.6(2) . . ?
 C21 B2 C15 110.5(2) . . ?
 C7 N1 B1 116.8(2) . . ?
 C2 C1 B1 118.2(2) . . ?
 C2 C1 C6B 116.1(4) . . ?
 C6A C1 C2 116.8(3) . . ?
 C6A C1 B1 124.5(3) . . ?
 C6B C1 B1 124.8(4) . . ?
 C3 C2 C1 120.9(3) . . ?
 F1 C3 C2 120.5(3) . . ?
 F1 C3 C4A 117.6(4) . . ?
 C2 C3 C4A 121.8(4) . . ?
 C4B C3 F1 116.8(5) . . ?
 C4B C3 C2 121.9(5) . . ?
 N1 C7 C8 112.3(2) . . ?
 N2 C8 C7 112.4(2) . . ?
 C10 C9 C14 117.1(3) . . ?
 C10 C9 B1 121.9(3) . . ?
 C14 C9 B1 120.9(3) . . ?
 C11 C10 C9 120.7(3) . . ?
 F4 C11 C10 120.2(4) . . ?
 F4 C11 C12 118.0(3) . . ?
 C12 C11 C10 121.8(3) . . ?
 F5 C12 C11 120.5(4) . . ?
 F5 C12 C13 121.1(4) . . ?
 C11 C12 C13 118.4(3) . . ?
 F6 C13 C12 118.5(3) . . ?
 F6 C13 C14 120.0(4) . . ?
 C12 C13 C14 121.4(3) . . ?
 C13 C14 C9 120.5(3) . . ?
 O1 B1 N1 105.8(2) . . ?
 O1 B1 C1 111.1(2) . . ?
 O1 B1 C9 114.9(2) . . ?
 C1 B1 N1 106.1(2) . . ?
 C1 B1 C9 111.1(2) . . ?
 C9 B1 N1 107.3(2) . . ?
 F2A C4A C3 122.8(15) . . ?
 F2A C4A C5A 119.5(16) . . ?
 C5A C4A C3 117.6(6) . . ?
 F3A C5A C4A 118.2(8) . . ?
 F3A C5A C6A 120.3(8) . . ?
 C6A C5A C4A 121.4(8) . . ?
 C5A C6A C1 121.0(5) . . ?
 C3 C4B C5B 117.3(9) . . ?
 F2B C4B C3 120(2) . . ?
 F2B C4B C5B 123(2) . . ?
 F3B C5B C4B 117.2(11) . . ?
 C6B C5B F3B 119.3(11) . . ?
 C6B C5B C4B 123.2(11) . . ?
 C5B C6B C1 119.4(8) . . ?

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
 C1S D1 F12 1.00 2.37 3.185(7) 138.1 1_455
 O2 H2C N4 0.75(5) 2.17(5) 2.900(3) 164(4) 2_565
 N3 H3A O1 0.87(3) 1.99(3) 2.830(3) 162(3) .
 N4 H4B F7 0.80(6) 2.38(6) 2.958(3) 130(5) 1_545
 O1 H1 N2 0.93(5) 1.94(5) 2.862(3) 170(5) 2_574
 N1 H1A O2 0.89(5) 1.97(5) 2.852(3) 173(4) .
 N1 H1B F1 0.83(4) 2.58(4) 3.089(3) 121(3) 2_565
 C7 H7A F10 0.99 2.53 3.167(3) 122.2 1_455

_shelx_SHELXL_version_number      '2014/7'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
  _twin_individual_id
  _twin_individual_mass_fraction_refined
 1 0.61(10)
 2 0.39(10)



#===END
