# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bfbmlb
_database_code_depnum_ccdc_archive 'CCDC 1935057'
loop_
_audit_author_name
_audit_author_address
'Neil Champness'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2019-06-19 deposited with the CCDC.	2020-02-05 downloaded from the CCDC.
;
_nottingham_internal_coll_name   BFBMLB
_nottingham_internal_coll_number 11005
_nottingham_internal_coll_client BM/NRC
_nottingham_internal_coll_type   ?
_nottingham_internal_coll_frame_method ?
_nottingham_internal_coll_frame_time ?
_nottingham_internal_coll_frame_width ?
_nottingham_internal_coll_user   NCS
_nottingham_internal_coll_date   ?
_nottingham_internal_coll_location SOTON
_nottingham_internal_coll_instrument ?
_nottingham_internal_NCS_number  2012NCS0008
_nottingham_internal_process_date ?
_nottingham_internal_process_user ?
_nottingham_internal_solution_date ?
_nottingham_internal_solution_user BM
_nottingham_internal_refinement_date 13/1/2012
_nottingham_internal_refinement_user BM
_nottingham_internal_self_archive_date 13/2/2012
_nottingham_internal_self_validation_date 13/2/2012
_nottingham_internal_self_validation_user BM
_nottingham_internal_validation_date 15/7/2015
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 15/7/2015
_refine_special_details          ?
_audit_creation_date             2019-06-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H16 B2 F4 N4'
_chemical_formula_sum            'C24 H16 B2 F4 N4'
_chemical_formula_weight         458.03
_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'
N N 0.0061 0.0033 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.0437(3)
_cell_length_b                   11.6835(6)
_cell_length_c                   14.5203(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.343(7)
_cell_angle_gamma                90
_cell_volume                     1019.02(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10097
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.375
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11280
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_min         3.318
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      100(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Mitegen
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2101
_reflns_number_total             2321
_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       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.073
_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)+(0.0402P)²+0.4437P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0890
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12)
;
_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 -0.12305(12) 0.34937(7) 0.44056(5) 0.02423(19) Uani 1 1 d . . . . .
F2 F 0.07534(12) 0.19586(6) 0.40283(5) 0.02262(18) Uani 1 1 d . . . . .
N1 N -0.18693(16) 0.27711(8) 0.28366(7) 0.0165(2) Uani 1 1 d . . . . .
N2 N 0.16266(16) 0.37851(8) 0.33892(6) 0.0171(2) Uani 1 1 d . . . . .
C1 C -0.3669(2) 0.20895(10) 0.27737(9) 0.0212(3) Uani 1 1 d . . . . .
H1 H -0.421030 0.170877 0.328169 0.025 Uiso 1 1 calc R . . . .
C2 C -0.4633(2) 0.20195(10) 0.18537(9) 0.0210(3) Uani 1 1 d . . . . .
H2 H -0.590751 0.158467 0.162850 0.025 Uiso 1 1 calc R . . . .
C3 C -0.33761(18) 0.27045(10) 0.13361(8) 0.0167(2) Uani 1 1 d . . . . .
H3 H -0.361739 0.282640 0.068586 0.020 Uiso 1 1 calc R . . . .
C4 C -0.16677(18) 0.31884(10) 0.19547(7) 0.0150(2) Uani 1 1 d . . . . .
C5 C 0.00255(17) 0.39531(9) 0.17941(7) 0.0139(2) Uani 1 1 d . . . . .
C6 C 0.16652(18) 0.42464(10) 0.25088(7) 0.0153(2) Uani 1 1 d . . . . .
C7 C 0.35349(18) 0.49739(10) 0.25252(8) 0.0175(2) Uani 1 1 d . . . . .
H7 H 0.395838 0.541252 0.202239 0.021 Uiso 1 1 calc R . . . .
C8 C 0.4631(2) 0.49269(11) 0.34105(8) 0.0215(3) Uani 1 1 d . . . . .
H8 H 0.596335 0.531804 0.363016 0.026 Uiso 1 1 calc R . . . .
C9 C 0.3404(2) 0.41930(11) 0.39230(8) 0.0221(3) Uani 1 1 d . . . . .
H9 H 0.377746 0.401012 0.455868 0.027 Uiso 1 1 calc R . . . .
C10 C 0.00198(17) 0.44758(9) 0.08667(7) 0.0138(2) Uani 1 1 d . . . . .
C11 C 0.18905(18) 0.44256(9) 0.03869(7) 0.0147(2) Uani 1 1 d . . . . .
H11 H 0.318325 0.403046 0.064876 0.018 Uiso 1 1 calc R . . . .
C12 C 0.18756(17) 0.49485(9) -0.04692(7) 0.0145(2) Uani 1 1 d . . . . .
H12 H 0.316355 0.491560 -0.078875 0.017 Uiso 1 1 calc R . . . .
B1 B -0.0202(2) 0.29910(11) 0.37078(9) 0.0178(3) 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 B1 1.3774(15) . ?
F2 B1 1.3948(14) . ?
N1 C1 1.3428(15) . ?
N1 C4 1.3881(14) . ?
N1 B1 1.5493(16) . ?
N2 C6 1.3898(14) . ?
N2 C9 1.3408(15) . ?
N2 B1 1.5522(16) . ?
C1 H1 0.9500 . ?
C1 C2 1.3996(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3816(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.4098(15) . ?
C4 C5 1.3973(15) . ?
C5 C6 1.3961(15) . ?
C5 C10 1.4783(15) . ?
C6 C7 1.4121(15) . ?
C7 H7 0.9500 . ?
C7 C8 1.3805(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.4003(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.3932(15) . ?
C10 C12 1.3970(14) 3_565 ?
C11 H11 0.9500 . ?
C11 C12 1.3842(15) . ?
C12 H12 0.9500 . ?

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
C1 N1 C4 107.37(9) . . ?
C1 N1 B1 127.06(10) . . ?
C4 N1 B1 125.42(9) . . ?
C6 N2 B1 126.22(9) . . ?
C9 N2 C6 107.47(10) . . ?
C9 N2 B1 126.25(10) . . ?
N1 C1 H1 124.8 . . ?
N1 C1 C2 110.39(10) . . ?
C2 C1 H1 124.8 . . ?
C1 C2 H2 126.6 . . ?
C3 C2 C1 106.81(10) . . ?
C3 C2 H2 126.6 . . ?
C2 C3 H3 126.5 . . ?
C2 C3 C4 107.08(10) . . ?
C4 C3 H3 126.5 . . ?
N1 C4 C3 108.31(10) . . ?
N1 C4 C5 121.27(10) . . ?
C5 C4 C3 130.42(10) . . ?
C4 C5 C10 119.21(9) . . ?
C6 C5 C4 120.38(10) . . ?
C6 C5 C10 120.38(10) . . ?
N2 C6 C5 120.39(10) . . ?
N2 C6 C7 108.21(9) . . ?
C5 C6 C7 131.40(10) . . ?
C6 C7 H7 126.5 . . ?
C8 C7 C6 107.01(10) . . ?
C8 C7 H7 126.5 . . ?
C7 C8 H8 126.5 . . ?
C7 C8 C9 106.95(10) . . ?
C9 C8 H8 126.5 . . ?
N2 C9 C8 110.35(10) . . ?
N2 C9 H9 124.8 . . ?
C8 C9 H9 124.8 . . ?
C11 C10 C5 121.18(9) . . ?
C11 C10 C12 119.17(10) . 3_565 ?
C12 C10 C5 119.64(10) 3_565 . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.35(10) . . ?
C12 C11 H11 119.8 . . ?
C10 C12 H12 119.8 3_565 . ?
C11 C12 C10 120.48(10) . 3_565 ?
C11 C12 H12 119.8 . . ?
F1 B1 F2 109.10(10) . . ?
F1 B1 N1 111.45(10) . . ?
F1 B1 N2 111.01(10) . . ?
F2 B1 N1 109.69(10) . . ?
F2 B1 N2 109.53(10) . . ?
N1 B1 N2 106.02(9) . . ?

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
N1 C1 C2 C3 -0.86(14) . . . . ?
N1 C4 C5 C6 5.06(16) . . . . ?
N1 C4 C5 C10 -173.03(10) . . . . ?
N2 C6 C7 C8 1.16(13) . . . . ?
C1 N1 C4 C3 -2.00(13) . . . . ?
C1 N1 C4 C5 178.28(10) . . . . ?
C1 N1 B1 F1 -62.29(15) . . . . ?
C1 N1 B1 F2 58.64(15) . . . . ?
C1 N1 B1 N2 176.82(11) . . . . ?
C1 C2 C3 C4 -0.40(13) . . . . ?
C2 C3 C4 N1 1.48(13) . . . . ?
C2 C3 C4 C5 -178.84(12) . . . . ?
C3 C4 C5 C6 -174.58(11) . . . . ?
C3 C4 C5 C10 7.33(18) . . . . ?
C4 N1 C1 C2 1.78(14) . . . . ?
C4 N1 B1 F1 122.69(11) . . . . ?
C4 N1 B1 F2 -116.38(12) . . . . ?
C4 N1 B1 N2 1.80(15) . . . . ?
C4 C5 C6 N2 -0.30(16) . . . . ?
C4 C5 C6 C7 179.16(11) . . . . ?
C4 C5 C10 C11 -127.40(11) . . . . ?
C4 C5 C10 C12 53.92(15) . . . 3_565 ?
C5 C6 C7 C8 -178.35(12) . . . . ?
C5 C10 C11 C12 -178.13(10) . . . . ?
C6 N2 C9 C8 0.22(14) . . . . ?
C6 N2 B1 F1 -118.06(12) . . . . ?
C6 N2 B1 F2 121.40(11) . . . . ?
C6 N2 B1 N1 3.12(15) . . . . ?
C6 C5 C10 C11 54.51(15) . . . . ?
C6 C5 C10 C12 -124.17(11) . . . 3_565 ?
C6 C7 C8 C9 -1.01(14) . . . . ?
C7 C8 C9 N2 0.51(15) . . . . ?
C9 N2 C6 C5 178.72(10) . . . . ?
C9 N2 C6 C7 -0.85(13) . . . . ?
C9 N2 B1 F1 58.71(15) . . . . ?
C9 N2 B1 F2 -61.83(15) . . . . ?
C9 N2 B1 N1 179.89(11) . . . . ?
C10 C5 C6 N2 177.77(10) . . . . ?
C10 C5 C6 C7 -2.77(18) . . . . ?
C10 C11 C12 C10 -0.56(18) . . . 3_565 ?
C12 C10 C11 C12 0.55(17) 3_565 . . . ?
B1 N1 C1 C2 -173.97(11) . . . . ?
B1 N1 C4 C3 173.83(10) . . . . ?
B1 N1 C4 C5 -5.88(17) . . . . ?
B1 N2 C6 C5 -4.01(17) . . . . ?
B1 N2 C6 C7 176.42(10) . . . . ?
B1 N2 C9 C8 -177.05(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bfbmld
_database_code_depnum_ccdc_archive 'CCDC 1935059'
loop_
_audit_author_name
_audit_author_address
'Neil Champness'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2019-06-19 deposited with the CCDC.	2020-02-05 downloaded from the CCDC.
;
_nottingham_internal_coll_name   BMBMLD
_nottingham_internal_coll_number 11209
_nottingham_internal_coll_client BM/NRC
_nottingham_internal_coll_type   hemisphere
_nottingham_internal_coll_frame_method \w
_nottingham_internal_coll_frame_time 40
_nottingham_internal_coll_frame_width 0.3
_nottingham_internal_coll_user   BM
_nottingham_internal_coll_date   27/2/2012
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument APEX
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 28/2/2012
_nottingham_internal_process_user BM/WL
_nottingham_internal_solution_date 28/2/2012
_nottingham_internal_solution_user BM
_nottingham_internal_refinement_date 28/2/2012
_nottingham_internal_refinement_user BM
_nottingham_internal_self_archive_date 29/2/2012
_nottingham_internal_self_validation_date 29/2/2012
_nottingham_internal_self_validation_user BM
_nottingham_internal_validation_date 15/7/2015
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 15/7/2015
_refine_special_details          ?
_audit_creation_date             2015-07-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H16 B2 F4 N4'
_chemical_formula_sum            'C24 H16 B2 F4 N4'
_chemical_formula_weight         458.03
_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'
N N 0.0061 0.0033 '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'

_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                   19.818(14)
_cell_length_b                   10.284(5)
_cell_length_c                   12.947(6)
_cell_angle_alpha                90
_cell_angle_beta                 130.539(7)
_cell_angle_gamma                90
_cell_volume                     2005.4(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1652
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.4
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2007/2 (Bruker,2007) was used for absorption correction.
wR2(int) was 0.0891 before and 0.0509 after correction.
The Ratio of minimum to maximum transmission is 0.7901.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5834
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.575
_diffrn_reflns_theta_min         2.398
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      90(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       ω
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1608
_reflns_number_total             2217
_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       'Bruker SAINT version 6.36A (Bruker, 2002)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.147
_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)+(0.0493P)²+1.2076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1365
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13)
;
_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 0.15854(9) 0.66246(12) 0.24681(13) 0.0239(4) Uani 1 1 d . . . . .
F2 F 0.16694(9) 0.82681(13) 0.14082(12) 0.0241(4) Uani 1 1 d . . . . .
N1 N 0.30312(13) 0.74860(18) 0.35151(17) 0.0195(4) Uani 1 1 d . . . . .
N2 N 0.19643(13) 0.87464(18) 0.34871(18) 0.0191(4) Uani 1 1 d . . . . .
C1 C 0.12251(16) 0.9124(2) 0.3235(2) 0.0214(5) Uani 1 1 d . . . . .
H1 H 0.0646 0.8811 0.2509 0.026 Uiso 1 1 calc R . . . .
C2 C 0.14263(17) 1.0045(2) 0.4190(2) 0.0232(5) Uani 1 1 d . . . . .
H2 H 0.1019 1.0460 0.4237 0.028 Uiso 1 1 calc R . . . .
C3 C 0.23308(16) 1.0235(2) 0.5052(2) 0.0220(5) Uani 1 1 d . . . . .
H3 H 0.2664 1.0805 0.5812 0.026 Uiso 1 1 calc R . . . .
C4 C 0.26720(16) 0.9440(2) 0.4609(2) 0.0188(5) Uani 1 1 d . . . . .
C5 C 0.35423(15) 0.9198(2) 0.5155(2) 0.0176(5) Uani 1 1 d . . . . .
C6 C 0.37167(15) 0.8238(2) 0.4599(2) 0.0186(5) Uani 1 1 d . . . . .
C7 C 0.45205(17) 0.7783(2) 0.4977(2) 0.0219(5) Uani 1 1 d . . . . .
H7 H 0.5096 0.8126 0.5673 0.026 Uiso 1 1 calc R . . . .
C8 C 0.43125(17) 0.6748(2) 0.4147(2) 0.0251(5) Uani 1 1 d . . . . .
H8 H 0.4720 0.6227 0.4175 0.030 Uiso 1 1 calc R . . . .
C9 C 0.33938(17) 0.6603(2) 0.3257(2) 0.0233(5) Uani 1 1 d . . . . .
H9 H 0.3072 0.5964 0.2562 0.028 Uiso 1 1 calc R . . . .
C10 C 0.42854(16) 0.9936(2) 0.6353(2) 0.0184(5) Uani 1 1 d . . . . .
C11 C 0.42889(16) 1.1287(2) 0.6366(2) 0.0221(5) Uani 1 1 d . . . . .
H11 H 0.3805 1.1757 0.5598 0.026 Uiso 1 1 calc R . . . .
C12 C 0.5000 1.1944(3) 0.7500 0.0246(8) Uani 1 2 d S T P . .
H12 H 0.5000 1.2867 0.7500 0.030 Uiso 1 2 calc RS T P . .
C13 C 0.5000 0.9274(3) 0.7500 0.0180(7) Uani 1 2 d S T P . .
H13 H 0.5000 0.8350 0.7500 0.022 Uiso 1 2 calc RS T P . .
B1 B 0.20301(18) 0.7750(2) 0.2665(2) 0.0189(6) 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 B1 1.375(3) . ?
F2 B1 1.389(3) . ?
N1 C6 1.391(3) . ?
N1 C9 1.329(3) . ?
N1 B1 1.544(4) . ?
N2 C1 1.335(3) . ?
N2 C4 1.392(3) . ?
N2 B1 1.543(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.394(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(3) . ?
C4 C5 1.397(4) . ?
C5 C6 1.390(3) . ?
C5 C10 1.477(3) . ?
C6 C7 1.408(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.371(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(3) . ?
C10 C13 1.393(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(3) . ?
C12 C11 1.382(3) 2_656 ?
C12 H12 0.9500 . ?
C13 C10 1.393(3) 2_656 ?
C13 H13 0.9500 . ?

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
C6 N1 B1 125.54(19) . . ?
C9 N1 C6 107.5(2) . . ?
C9 N1 B1 126.55(19) . . ?
C1 N2 C4 107.9(2) . . ?
C1 N2 B1 126.6(2) . . ?
C4 N2 B1 125.5(2) . . ?
N2 C1 H1 124.9 . . ?
N2 C1 C2 110.2(2) . . ?
C2 C1 H1 124.9 . . ?
C1 C2 H2 126.7 . . ?
C3 C2 C1 106.6(2) . . ?
C3 C2 H2 126.7 . . ?
C2 C3 H3 126.1 . . ?
C2 C3 C4 107.8(2) . . ?
C4 C3 H3 126.1 . . ?
N2 C4 C3 107.4(2) . . ?
N2 C4 C5 120.8(2) . . ?
C5 C4 C3 131.5(2) . . ?
C4 C5 C10 120.0(2) . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 C10 119.6(2) . . ?
N1 C6 C7 107.9(2) . . ?
C5 C6 N1 120.6(2) . . ?
C5 C6 C7 131.4(2) . . ?
C6 C7 H7 126.6 . . ?
C8 C7 C6 106.8(2) . . ?
C8 C7 H7 126.6 . . ?
C7 C8 H8 126.4 . . ?
C7 C8 C9 107.3(2) . . ?
C9 C8 H8 126.4 . . ?
N1 C9 C8 110.4(2) . . ?
N1 C9 H9 124.8 . . ?
C8 C9 H9 124.8 . . ?
C11 C10 C5 121.3(2) . . ?
C11 C10 C13 118.8(2) . . ?
C13 C10 C5 119.8(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C11 121.5(3) 2_656 . ?
C11 C12 H12 119.3 2_656 . ?
C11 C12 H12 119.3 . . ?
C10 C13 C10 121.5(3) 2_656 . ?
C10 C13 H13 119.3 . . ?
C10 C13 H13 119.3 2_656 . ?
F1 B1 F2 109.03(18) . . ?
F1 B1 N1 110.85(19) . . ?
F1 B1 N2 110.8(2) . . ?
F2 B1 N1 110.3(2) . . ?
F2 B1 N2 110.10(19) . . ?
N2 B1 N1 105.70(18) . . ?

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
N1 C6 C7 C8 -1.6(3) . . . . ?
N2 C1 C2 C3 0.5(3) . . . . ?
N2 C4 C5 C6 -1.3(3) . . . . ?
N2 C4 C5 C10 -179.43(19) . . . . ?
C1 N2 C4 C3 1.6(2) . . . . ?
C1 N2 C4 C5 176.6(2) . . . . ?
C1 N2 B1 F1 -50.1(3) . . . . ?
C1 N2 B1 F2 70.6(3) . . . . ?
C1 N2 B1 N1 -170.3(2) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 N2 -1.3(3) . . . . ?
C2 C3 C4 C5 -175.6(2) . . . . ?
C3 C4 C5 C6 172.4(2) . . . . ?
C3 C4 C5 C10 -5.8(4) . . . . ?
C4 N2 C1 C2 -1.3(2) . . . . ?
C4 N2 B1 F1 131.9(2) . . . . ?
C4 N2 B1 F2 -107.4(2) . . . . ?
C4 N2 B1 N1 11.8(3) . . . . ?
C4 C5 C6 N1 -1.5(3) . . . . ?
C4 C5 C6 C7 -177.8(2) . . . . ?
C4 C5 C10 C11 -53.8(3) . . . . ?
C4 C5 C10 C13 126.2(2) . . . . ?
C5 C6 C7 C8 175.0(2) . . . . ?
C5 C10 C11 C12 -179.33(19) . . . . ?
C5 C10 C13 C10 179.7(2) . . . 2_656 ?
C6 N1 C9 C8 -0.1(3) . . . . ?
C6 N1 B1 F1 -134.8(2) . . . . ?
C6 N1 B1 F2 104.3(2) . . . . ?
C6 N1 B1 N2 -14.7(3) . . . . ?
C6 C5 C10 C11 128.0(3) . . . . ?
C6 C5 C10 C13 -52.0(3) . . . . ?
C6 C7 C8 C9 1.6(3) . . . . ?
C7 C8 C9 N1 -1.0(3) . . . . ?
C9 N1 C6 C5 -176.0(2) . . . . ?
C9 N1 C6 C7 1.0(2) . . . . ?
C9 N1 B1 F1 53.5(3) . . . . ?
C9 N1 B1 F2 -67.4(3) . . . . ?
C9 N1 B1 N2 173.6(2) . . . . ?
C10 C5 C6 N1 176.64(19) . . . . ?
C10 C5 C6 C7 0.4(4) . . . . ?
C10 C11 C12 C11 -0.36(18) . . . 2_656 ?
C11 C10 C13 C10 -0.35(17) . . . 2_656 ?
C13 C10 C11 C12 0.7(3) . . . . ?
B1 N1 C6 C5 11.0(3) . . . . ?
B1 N1 C6 C7 -172.0(2) . . . . ?
B1 N1 C9 C8 172.9(2) . . . . ?
B1 N2 C1 C2 -179.5(2) . . . . ?
B1 N2 C4 C3 179.88(19) . . . . ?
B1 N2 C4 C5 -5.1(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bfbmle
_database_code_depnum_ccdc_archive 'CCDC 1935058'
loop_
_audit_author_name
_audit_author_address
'Neil Champness'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2019-06-19 deposited with the CCDC.	2020-02-05 downloaded from the CCDC.
;
_nottingham_internal_coll_name   BFBMLE
_nottingham_internal_coll_number 11210
_nottingham_internal_coll_client BM/NRC
_nottingham_internal_coll_type   ?
_nottingham_internal_coll_frame_method \w
_nottingham_internal_coll_frame_time 1
_nottingham_internal_coll_frame_width 1
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   19/3/2012
_nottingham_internal_coll_location DLS
_nottingham_internal_coll_instrument 'EH1, I19, DLS'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 19/3/2012
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date ?
_nottingham_internal_solution_user BM
_nottingham_internal_refinement_date 15/7/2015
_nottingham_internal_refinement_user BM/pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 15/7/2015
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 15/7/2015
_refine_special_details          
;
The crystal was determined to be a 2-component psuedo-merohedral twin, 
and was treated with PLATON TWINROTMATR to deconvolute the two twin 
components.

The haf-occupied dichloromethane moleucle is disordered over three sites. 
The occupancies were refined competitvely, converging at a ratio of 
0.163:0.171:0.164. The C-Cl distances were tightly restrained to 1.732 Å, 
while the Cl-Cl distances were tightly restrained to 2.883 Å - both values 
were dervied from the average of 5940 good quality structures from the CCDC 
(data extracted 15/7/2015). The partially occupied molecules were refined 
with fixed thermal parameters, as with the large amount of overlap they 
could not be sensibly refined with freely refining thermal parameters.
;
_vrf_PLAT084_bfbmle              
;
PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.37 Report
RESPONSE: The sample crystalises as extremely small crystals, which required 
collection at a synchrotron. Despite accounting for the twinning, the overall 
data quality is still relatively poor, which has resulted in a high wR2 value.
;
_vrf_RFACR01_bfbmle              
;
PROBLEM: The value of the weighted R factor is > 0.35
RESPONSE: The sample crystalises as extremely small crystals, which required 
collection at a synchrotron. Despite accounting for the twinning, the overall 
data quality is still relatively poor, which has resulted in a high wR2 value.
;
_audit_creation_date             2015-07-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H21 B3 F6 N6, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C33.50 H22 B3 Cl F6 N6'
_chemical_formula_weight         690.45
_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 0.0030 0.0020 '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 0.0010 0.0010 '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 0.0160 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 '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                   20.50(2)
_cell_length_b                   20.40(2)
_cell_length_c                   8.110(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.68
_cell_angle_gamma                90
_cell_volume                     3374(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7702
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.7
_cell_measurement_theta_min      1.5
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1404
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0836
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5765
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        24.209
_diffrn_reflns_theta_max         24.209
_diffrn_reflns_theta_min         2.164
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
scan:
	Number of images: 126
	           Slice: -10.0000 - 116.0000
	     Image width: 1.0000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 50.0000
	             Phi: 0.0000
	             XTD: 59.5978
	          2theta: 30.2550
scan:
	Number of images: 126
	           Slice: -10.0000 - 116.0000
	     Image width: 1.0000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 50.0000
	             Phi: 90.0000
	             XTD: 59.5978
	          2theta: 30.2550
scan:
	Number of images: 126
	           Slice: -10.0000 - 116.0000
	     Image width: 1.0000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 50.0000
	             Phi: 270.0000
	             XTD: 59.5978
	          2theta: 30.2550
scan:
	Number of images: 58
	           Slice: 26.0000 - 84.0000
	     Image width: 1.0000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 50.0000
	             Phi: 120.0000
	             XTD: 59.5978
	          2theta: 30.2550
scan:
	Number of images: 47
	           Slice: -21.0000 - 26.0000
	     Image width: 1.0000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -10.0000
	             Phi: 270.0000
	             XTD: 59.5978
	          2theta: 30.2550
scan:
	Number of images: 27
	           Slice: -10.0000 - 17.0000
	     Image width: 1.0000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 50.0000
	             Phi: 240.0000
	             XTD: 59.5978
	          2theta: 30.2550
scan:
	Number of images: 23
	           Slice: -12.0000 - 11.0000
	     Image width: 1.0000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 10.0000
	             Phi: 0.0000
	             XTD: 59.5978
	          2theta: 30.2550
;
_diffrn_measurement_device       
;
CrystalLogic Kappa (3 circle)
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.063057
_diffrn_orient_matrix_UB_12      -0.075511
_diffrn_orient_matrix_UB_13      0.074326
_diffrn_orient_matrix_UB_21      -0.001196
_diffrn_orient_matrix_UB_22      0.009049
_diffrn_orient_matrix_UB_23      0.008179
_diffrn_orient_matrix_UB_31      -0.041858
_diffrn_orient_matrix_UB_32      0.013848
_diffrn_orient_matrix_UB_33      -0.021443
_diffrn_radiation_monochromator  Synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_source                   Synchrotron
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3903
_reflns_number_total             5765
_reflns_special_details          
;
 _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       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.304
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     464
_refine_ls_number_reflns         5765
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1635
_refine_ls_R_factor_gt           0.1329
_refine_ls_restrained_S_all      1.305
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3379
_refine_ls_wR_factor_ref         0.3730
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.467(4) 0.533(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Restrained distances
 Cl6-C36 = Cl5-C36 = Cl4-C34 = Cl3-C34 = Cl1-C35 = Cl2-C35
 1.732 with sigma of 0.01
 Cl1-Cl2 = Cl6-Cl5 = Cl4-Cl3
 2.883 with sigma of 0.01
4. Others
 1*[Sof(C34)+Sof(H34A)+Sof(H34B)+Sof(Cl3)+Sof(Cl4)]+1*[Sof(C35)+Sof(H35A)+
 Sof(H35B)+Sof(Cl1)+Sof(Cl2)]+1*[Sof(C36)+Sof(H36A)+Sof(H36B)+Sof(Cl5)+
 Sof(Cl6)]=0.5 with esd of 0.001
 Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(Cl3)=Sof(Cl4)=FVAR(1)
 Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(Cl1)=Sof(Cl2)=FVAR(2)
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(Cl5)=Sof(Cl6)=FVAR(3)
 Fixed Uiso: C34(0.1) Cl3(0.1) Cl4(0.1) C36(0.1) Cl5(0.1) Cl6(0.1) C35(0.1)
 Cl1(0.1) Cl2(0.1)
5.a Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B), C36(H36A,H36B), C35(H35A,H35B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C25(H25), C26(H26),
  C27(H27), C29(H29), C31(H31), C33(H33)
;
_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
B1 B 0.2541(3) 0.8211(3) 0.6579(9) 0.0374(15) Uani 1 1 d . . . . .
B2 B 0.0260(4) 0.4067(5) 0.2775(12) 0.057(2) Uani 1 1 d . . . . .
B3 B 0.4686(4) 0.3860(4) 1.0276(11) 0.0486(18) Uani 1 1 d . . . . .
C1 C 0.3695(3) 0.7940(3) 0.5676(9) 0.0454(15) Uani 1 1 d . . . . .
H1 H 0.3826 0.8381 0.5530 0.054 Uiso 1 1 calc R . . . .
C2 C 0.4075(3) 0.7383(3) 0.5379(9) 0.0460(16) Uani 1 1 d . . . . .
H2 H 0.4499 0.7379 0.5001 0.055 Uiso 1 1 calc R . . . .
C3 C 0.3707(3) 0.6845(3) 0.5750(8) 0.0420(15) Uani 1 1 d . . . . .
H3 H 0.3837 0.6400 0.5670 0.050 Uiso 1 1 calc R . . . .
C4 C 0.3101(3) 0.7065(3) 0.6272(8) 0.0375(14) Uani 1 1 d . . . . .
C5 C 0.2535(3) 0.6736(3) 0.6646(8) 0.0387(14) Uani 1 1 d . . . . .
C6 C 0.1977(3) 0.7084(3) 0.6943(8) 0.0358(13) Uani 1 1 d . . . . .
C7 C 0.1345(3) 0.6877(3) 0.7434(9) 0.0411(14) Uani 1 1 d . . . . .
H7 H 0.1212 0.6438 0.7609 0.049 Uiso 1 1 calc R . . . .
C8 C 0.0974(3) 0.7432(3) 0.7599(9) 0.0469(16) Uani 1 1 d . . . . .
H8 H 0.0538 0.7444 0.7899 0.056 Uiso 1 1 calc R . . . .
C9 C 0.1360(3) 0.7980(3) 0.7243(11) 0.0508(18) Uani 1 1 d . . . . .
H9 H 0.1221 0.8424 0.7254 0.061 Uiso 1 1 calc R . . . .
C10 C 0.0805(3) 0.4744(3) 0.0593(9) 0.0535(18) Uani 1 1 d . . . . .
H10 H 0.0503 0.4625 -0.0323 0.064 Uiso 1 1 calc R . . . .
C11 C 0.1335(3) 0.5168(3) 0.0495(10) 0.0506(17) Uani 1 1 d . . . . .
H11 H 0.1454 0.5383 -0.0471 0.061 Uiso 1 1 calc R . . . .
C12 C 0.1655(3) 0.5213(3) 0.2072(9) 0.0488(17) Uani 1 1 d . . . . .
H12 H 0.2032 0.5469 0.2407 0.059 Uiso 1 1 calc R . . . .
C13 C 0.1306(3) 0.4803(3) 0.3091(9) 0.0426(15) Uani 1 1 d . . . . .
C14 C 0.1443(3) 0.4639(3) 0.4774(9) 0.0422(15) Uani 1 1 d . . . . .
C15 C 0.1058(3) 0.4167(3) 0.5519(9) 0.0493(17) Uani 1 1 d . . . . .
C16 C 0.1099(4) 0.3902(4) 0.7131(11) 0.064(2) Uani 1 1 d . . . . .
H16 H 0.1407 0.4015 0.8039 0.077 Uiso 1 1 calc R . . . .
C17 C 0.0597(5) 0.3439(5) 0.7128(12) 0.090(3) Uani 1 1 d . . . . .
H17 H 0.0496 0.3181 0.8043 0.108 Uiso 1 1 calc R . . . .
C18 C 0.0274(4) 0.3427(5) 0.5543(13) 0.090(3) Uani 1 1 d . . . . .
H18 H -0.0080 0.3142 0.5195 0.107 Uiso 1 1 calc R . . . .
C19 C 0.4639(4) 0.3329(4) 0.7348(11) 0.073(3) Uani 1 1 d . . . . .
H19 H 0.4989 0.3028 0.7591 0.088 Uiso 1 1 calc R . . . .
C20 C 0.4285(4) 0.3403(4) 0.5811(10) 0.071(2) Uani 1 1 d . . . . .
H20 H 0.4349 0.3165 0.4832 0.085 Uiso 1 1 calc R . . . .
C21 C 0.3814(4) 0.3892(4) 0.5969(9) 0.0586(19) Uani 1 1 d . . . . .
H21 H 0.3501 0.4047 0.5118 0.070 Uiso 1 1 calc R . . . .
C22 C 0.3893(3) 0.4112(3) 0.7623(9) 0.0466(16) Uani 1 1 d . . . . .
C23 C 0.3560(3) 0.4584(3) 0.8451(8) 0.0389(14) Uani 1 1 d . . . . .
C24 C 0.3739(3) 0.4737(3) 1.0116(9) 0.0414(15) Uani 1 1 d . . . . .
C25 C 0.3470(3) 0.5170(3) 1.1216(9) 0.0450(15) Uani 1 1 d . . . . .
H25 H 0.3094 0.5438 1.0977 0.054 Uiso 1 1 calc R . . . .
C26 C 0.3855(3) 0.5132(3) 1.2706(10) 0.0535(18) Uani 1 1 d . . . . .
H26 H 0.3803 0.5379 1.3677 0.064 Uiso 1 1 calc R . . . .
C27 C 0.4341(4) 0.4654(3) 1.2511(10) 0.059(2) Uani 1 1 d . . . . .
H27 H 0.4665 0.4522 1.3363 0.071 Uiso 1 1 calc R . . . .
C28 C 0.2520(2) 0.5999(3) 0.6663(8) 0.0362(13) Uani 1 1 d . . . . .
C29 C 0.2011(3) 0.5664(3) 0.5778(8) 0.0392(14) Uani 1 1 d . . . . .
H29 H 0.1672 0.5904 0.5167 0.047 Uiso 1 1 calc R . . . .
C30 C 0.1990(3) 0.4980(3) 0.5769(8) 0.0391(14) Uani 1 1 d . . . . .
C31 C 0.2490(3) 0.4624(3) 0.6662(9) 0.0408(14) Uani 1 1 d . . . . .
H31 H 0.2472 0.4159 0.6689 0.049 Uiso 1 1 calc R . . . .
C32 C 0.3017(3) 0.4954(3) 0.7516(8) 0.0400(14) Uani 1 1 d . . . . .
C33 C 0.3029(3) 0.5645(3) 0.7531(8) 0.0384(14) Uani 1 1 d . . . . .
H33 H 0.3383 0.5871 0.8129 0.046 Uiso 1 1 calc R . . . .
F1 F 0.27286(16) 0.86017(16) 0.7965(4) 0.0427(9) Uani 1 1 d . . . . .
F2 F 0.23889(15) 0.86400(16) 0.5234(4) 0.0387(8) Uani 1 1 d . . . . .
F3 F -0.0335(2) 0.4378(3) 0.2813(7) 0.0846(17) Uani 1 1 d . . . . .
F4 F 0.0192(3) 0.3513(2) 0.1766(6) 0.0795(15) Uani 1 1 d . . . . .
F5 F 0.4606(2) 0.32685(19) 1.1164(6) 0.0644(12) Uani 1 1 d . . . . .
F6 F 0.53424(18) 0.4006(2) 1.0428(6) 0.0641(12) Uani 1 1 d . . . . .
N1 N 0.3109(2) 0.7749(2) 0.6205(7) 0.0346(11) Uani 1 1 d . . . . .
N2 N 0.1963(2) 0.7772(2) 0.6881(7) 0.0364(12) Uani 1 1 d . . . . .
N3 N 0.0775(2) 0.4527(3) 0.2149(7) 0.0467(13) Uani 1 1 d . . . . .
N4 N 0.0527(3) 0.3867(3) 0.4572(8) 0.0557(16) Uani 1 1 d . . . . .
N5 N 0.4412(3) 0.3754(3) 0.8461(8) 0.0497(14) Uani 1 1 d . . . . .
N6 N 0.4284(2) 0.4410(3) 1.0963(7) 0.0446(13) Uani 1 1 d . . . . .
C34 C 0.2917(10) 0.324(4) 0.169(3) 0.100 Uiso 0.163(3) 1 d D . P A 1
H34A H 0.3132 0.3656 0.2072 0.120 Uiso 0.163(3) 1 calc R . P A 1
H34B H 0.3034 0.2903 0.2551 0.120 Uiso 0.163(3) 1 calc R . P A 1
Cl3 Cl 0.3203(7) 0.3000(8) -0.015(3) 0.100 Uiso 0.163(3) 1 d D . P A 1
Cl4 Cl 0.2076(8) 0.3349(9) 0.148(2) 0.100 Uiso 0.163(3) 1 d D . P A 1
C36 C 0.2490(10) 0.300(4) 0.193(5) 0.100 Uiso 0.164(3) 1 d D . P B 3
H36A H 0.2683 0.2563 0.2109 0.120 Uiso 0.164(3) 1 calc R . P B 3
H36B H 0.2783 0.3262 0.1274 0.120 Uiso 0.164(3) 1 calc R . P B 3
Cl5 Cl 0.1729(8) 0.2934(8) 0.081(2) 0.100 Uiso 0.164(3) 1 d D . P B 3
Cl6 Cl 0.2443(8) 0.3382(9) 0.382(2) 0.100 Uiso 0.164(3) 1 d D . P B 3
C35 C 0.2978(19) 0.2865(9) 0.257(9) 0.100 Uiso 0.171(4) 1 d D . P C 2
H35A H 0.3408 0.2823 0.2118 0.120 Uiso 0.171(4) 1 calc R . P C 2
H35B H 0.3056 0.2878 0.3791 0.120 Uiso 0.171(4) 1 calc R . P C 2
Cl1 Cl 0.2607(8) 0.3590(6) 0.187(2) 0.100 Uiso 0.171(4) 1 d D . P C 2
Cl2 Cl 0.2500(7) 0.2192(6) 0.198(3) 0.100 Uiso 0.171(4) 1 d D . P C 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
B1 F1 1.400(7) . ?
B1 F2 1.409(8) . ?
B1 N1 1.550(8) . ?
B1 N2 1.524(8) . ?
B2 F3 1.377(10) . ?
B2 F4 1.395(10) . ?
B2 N3 1.537(11) . ?
B2 N4 1.560(11) . ?
B3 F5 1.423(9) . ?
B3 F6 1.372(9) . ?
B3 N5 1.539(10) . ?
B3 N6 1.529(10) . ?
C1 H1 0.9500 . ?
C1 C2 1.411(9) . ?
C1 N1 1.372(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.424(8) . ?
C4 C5 1.399(9) . ?
C4 N1 1.397(7) . ?
C5 C6 1.388(8) . ?
C5 C28 1.503(8) . ?
C6 C7 1.455(8) . ?
C6 N2 1.406(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.377(9) . ?
C8 H8 0.9500 . ?
C8 C9 1.416(10) . ?
C9 H9 0.9500 . ?
C9 N2 1.365(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.397(10) . ?
C10 N3 1.344(10) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(10) . ?
C12 H12 0.9500 . ?
C12 C13 1.417(10) . ?
C13 C14 1.407(10) . ?
C13 N3 1.386(8) . ?
C14 C15 1.416(10) . ?
C14 C30 1.488(8) . ?
C15 C16 1.410(11) . ?
C15 N4 1.409(8) . ?
C16 H16 0.9500 . ?
C16 C17 1.396(11) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(13) . ?
C18 H18 0.9500 . ?
C18 N4 1.333(11) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(11) . ?
C19 N5 1.366(10) . ?
C20 H20 0.9500 . ?
C20 C21 1.403(10) . ?
C21 H21 0.9500 . ?
C21 C22 1.408(10) . ?
C22 C23 1.390(9) . ?
C22 N5 1.408(7) . ?
C23 C24 1.399(9) . ?
C23 C32 1.491(8) . ?
C24 C25 1.406(10) . ?
C24 N6 1.418(7) . ?
C25 H25 0.9500 . ?
C25 C26 1.378(10) . ?
C26 H26 0.9500 . ?
C26 C27 1.413(10) . ?
C27 H27 0.9500 . ?
C27 N6 1.345(9) . ?
C28 C29 1.386(8) . ?
C28 C33 1.401(8) . ?
C29 H29 0.9500 . ?
C29 C30 1.395(9) . ?
C30 C31 1.399(8) . ?
C31 H31 0.9500 . ?
C31 C32 1.397(8) . ?
C32 C33 1.409(9) . ?
C33 H33 0.9500 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 Cl3 1.729(10) . ?
C34 Cl4 1.730(10) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 Cl5 1.730(10) . ?
C36 Cl6 1.729(10) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 Cl1 1.733(10) . ?
C35 Cl2 1.726(10) . ?

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
F1 B1 F2 106.9(5) . . ?
F1 B1 N1 110.6(4) . . ?
F1 B1 N2 111.2(6) . . ?
F2 B1 N1 109.8(5) . . ?
F2 B1 N2 111.9(4) . . ?
N2 B1 N1 106.6(5) . . ?
F3 B2 F4 110.5(6) . . ?
F3 B2 N3 111.4(7) . . ?
F3 B2 N4 109.2(7) . . ?
F4 B2 N3 109.5(7) . . ?
F4 B2 N4 109.9(7) . . ?
N3 B2 N4 106.2(5) . . ?
F5 B3 N5 108.4(6) . . ?
F5 B3 N6 110.2(7) . . ?
F6 B3 F5 107.3(5) . . ?
F6 B3 N5 112.3(7) . . ?
F6 B3 N6 111.6(6) . . ?
N6 B3 N5 107.0(5) . . ?
C2 C1 H1 125.0 . . ?
N1 C1 H1 125.0 . . ?
N1 C1 C2 109.9(5) . . ?
C1 C2 H2 126.9 . . ?
C3 C2 C1 106.2(5) . . ?
C3 C2 H2 126.9 . . ?
C2 C3 H3 125.5 . . ?
C2 C3 C4 109.0(5) . . ?
C4 C3 H3 125.5 . . ?
C5 C4 C3 132.8(5) . . ?
N1 C4 C3 106.8(5) . . ?
N1 C4 C5 120.1(5) . . ?
C4 C5 C28 120.0(5) . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 C28 119.4(5) . . ?
C5 C6 C7 132.1(5) . . ?
C5 C6 N2 121.3(5) . . ?
N2 C6 C7 106.6(5) . . ?
C6 C7 H7 126.2 . . ?
C8 C7 C6 107.6(5) . . ?
C8 C7 H7 126.2 . . ?
C7 C8 H8 126.1 . . ?
C7 C8 C9 107.8(6) . . ?
C9 C8 H8 126.1 . . ?
C8 C9 H9 125.2 . . ?
N2 C9 C8 109.6(6) . . ?
N2 C9 H9 125.2 . . ?
C11 C10 H10 124.3 . . ?
N3 C10 H10 124.3 . . ?
N3 C10 C11 111.4(6) . . ?
C10 C11 H11 126.6 . . ?
C12 C11 C10 106.8(7) . . ?
C12 C11 H11 126.6 . . ?
C11 C12 H12 126.9 . . ?
C11 C12 C13 106.3(6) . . ?
C13 C12 H12 126.9 . . ?
C14 C13 C12 130.1(6) . . ?
N3 C13 C12 109.4(6) . . ?
N3 C13 C14 120.5(6) . . ?
C13 C14 C15 120.7(5) . . ?
C13 C14 C30 118.8(6) . . ?
C15 C14 C30 120.5(6) . . ?
C16 C15 C14 132.2(6) . . ?
N4 C15 C14 119.7(6) . . ?
N4 C15 C16 108.1(6) . . ?
C15 C16 H16 126.8 . . ?
C17 C16 C15 106.4(7) . . ?
C17 C16 H16 126.8 . . ?
C16 C17 H17 126.3 . . ?
C18 C17 C16 107.4(8) . . ?
C18 C17 H17 126.3 . . ?
C17 C18 H18 124.5 . . ?
N4 C18 C17 110.9(7) . . ?
N4 C18 H18 124.5 . . ?
C20 C19 H19 125.0 . . ?
N5 C19 H19 125.0 . . ?
N5 C19 C20 110.1(6) . . ?
C19 C20 H20 126.3 . . ?
C19 C20 C21 107.3(7) . . ?
C21 C20 H20 126.3 . . ?
C20 C21 H21 126.3 . . ?
C20 C21 C22 107.4(6) . . ?
C22 C21 H21 126.3 . . ?
C21 C22 N5 107.7(6) . . ?
C23 C22 C21 131.7(6) . . ?
C23 C22 N5 120.6(6) . . ?
C22 C23 C24 121.8(6) . . ?
C22 C23 C32 118.9(6) . . ?
C24 C23 C32 119.3(6) . . ?
C23 C24 C25 132.1(6) . . ?
C23 C24 N6 118.8(6) . . ?
C25 C24 N6 109.1(6) . . ?
C24 C25 H25 126.4 . . ?
C26 C25 C24 107.2(6) . . ?
C26 C25 H25 126.4 . . ?
C25 C26 H26 126.6 . . ?
C25 C26 C27 106.8(7) . . ?
C27 C26 H26 126.6 . . ?
C26 C27 H27 124.4 . . ?
N6 C27 C26 111.2(6) . . ?
N6 C27 H27 124.4 . . ?
C29 C28 C5 120.3(5) . . ?
C29 C28 C33 119.4(5) . . ?
C33 C28 C5 120.3(5) . . ?
C28 C29 H29 119.4 . . ?
C28 C29 C30 121.2(5) . . ?
C30 C29 H29 119.4 . . ?
C29 C30 C14 119.5(5) . . ?
C29 C30 C31 119.6(5) . . ?
C31 C30 C14 120.8(5) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 C30 119.8(5) . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C23 120.6(5) . . ?
C31 C32 C33 120.0(5) . . ?
C33 C32 C23 119.4(5) . . ?
C28 C33 C32 119.9(5) . . ?
C28 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C1 N1 B1 125.9(5) . . ?
C1 N1 C4 108.0(5) . . ?
C4 N1 B1 126.0(5) . . ?
C6 N2 B1 125.4(5) . . ?
C9 N2 B1 126.0(5) . . ?
C9 N2 C6 108.5(5) . . ?
C10 N3 B2 127.4(6) . . ?
C10 N3 C13 106.1(6) . . ?
C13 N3 B2 126.5(6) . . ?
C15 N4 B2 125.2(6) . . ?
C18 N4 B2 127.4(6) . . ?
C18 N4 C15 107.2(6) . . ?
C19 N5 B3 127.3(5) . . ?
C19 N5 C22 107.5(6) . . ?
C22 N5 B3 125.1(5) . . ?
C24 N6 B3 126.5(6) . . ?
C27 N6 B3 127.7(6) . . ?
C27 N6 C24 105.7(5) . . ?
H34A C34 H34B 108.0 . . ?
Cl3 C34 H34A 109.3 . . ?
Cl3 C34 H34B 109.3 . . ?
Cl3 C34 Cl4 111.5(9) . . ?
Cl4 C34 H34A 109.3 . . ?
Cl4 C34 H34B 109.3 . . ?
H36A C36 H36B 107.9 . . ?
Cl5 C36 H36A 109.2 . . ?
Cl5 C36 H36B 109.2 . . ?
Cl6 C36 H36A 109.2 . . ?
Cl6 C36 H36B 109.2 . . ?
Cl6 C36 Cl5 112.1(9) . . ?
H35A C35 H35B 107.9 . . ?
Cl1 C35 H35A 109.3 . . ?
Cl1 C35 H35B 109.3 . . ?
Cl2 C35 H35A 109.3 . . ?
Cl2 C35 H35B 109.3 . . ?
Cl2 C35 Cl1 111.7(9) . . ?

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 C2 C3 C4 0.1(7) . . . . ?
C2 C1 N1 B1 -176.8(6) . . . . ?
C2 C1 N1 C4 0.4(7) . . . . ?
C2 C3 C4 C5 173.6(7) . . . . ?
C2 C3 C4 N1 0.2(7) . . . . ?
C3 C4 C5 C6 -172.3(6) . . . . ?
C3 C4 C5 C28 5.3(10) . . . . ?
C3 C4 N1 B1 176.9(5) . . . . ?
C3 C4 N1 C1 -0.3(7) . . . . ?
C4 C5 C6 C7 -176.3(6) . . . . ?
C4 C5 C6 N2 -0.1(9) . . . . ?
C4 C5 C28 C29 -128.9(7) . . . . ?
C4 C5 C28 C33 49.1(9) . . . . ?
C5 C4 N1 B1 2.5(9) . . . . ?
C5 C4 N1 C1 -174.8(6) . . . . ?
C5 C6 C7 C8 178.3(7) . . . . ?
C5 C6 N2 B1 -3.1(9) . . . . ?
C5 C6 N2 C9 -179.2(6) . . . . ?
C5 C28 C29 C30 179.6(6) . . . . ?
C5 C28 C33 C32 -178.8(6) . . . . ?
C6 C5 C28 C29 48.8(9) . . . . ?
C6 C5 C28 C33 -133.2(6) . . . . ?
C6 C7 C8 C9 -0.6(8) . . . . ?
C7 C6 N2 B1 173.9(6) . . . . ?
C7 C6 N2 C9 -2.1(7) . . . . ?
C7 C8 C9 N2 -0.7(8) . . . . ?
C8 C9 N2 B1 -174.2(6) . . . . ?
C8 C9 N2 C6 1.8(8) . . . . ?
C10 C11 C12 C13 0.7(8) . . . . ?
C11 C10 N3 B2 178.7(7) . . . . ?
C11 C10 N3 C13 -1.3(8) . . . . ?
C11 C12 C13 C14 175.7(7) . . . . ?
C11 C12 C13 N3 -1.5(8) . . . . ?
C12 C13 C14 C15 -174.1(7) . . . . ?
C12 C13 C14 C30 7.3(11) . . . . ?
C12 C13 N3 B2 -178.3(6) . . . . ?
C12 C13 N3 C10 1.7(8) . . . . ?
C13 C14 C15 C16 177.8(8) . . . . ?
C13 C14 C15 N4 -0.9(10) . . . . ?
C13 C14 C30 C29 52.2(9) . . . . ?
C13 C14 C30 C31 -126.2(7) . . . . ?
C14 C13 N3 B2 4.2(10) . . . . ?
C14 C13 N3 C10 -175.8(6) . . . . ?
C14 C15 C16 C17 -178.1(8) . . . . ?
C14 C15 N4 B2 -7.8(11) . . . . ?
C14 C15 N4 C18 177.0(8) . . . . ?
C14 C30 C31 C32 176.6(7) . . . . ?
C15 C14 C30 C29 -126.4(7) . . . . ?
C15 C14 C30 C31 55.2(9) . . . . ?
C15 C16 C17 C18 0.8(13) . . . . ?
C16 C15 N4 B2 173.2(7) . . . . ?
C16 C15 N4 C18 -2.0(10) . . . . ?
C16 C17 C18 N4 -2.1(15) . . . . ?
C17 C18 N4 B2 -172.5(9) . . . . ?
C17 C18 N4 C15 2.5(13) . . . . ?
C19 C20 C21 C22 0.1(11) . . . . ?
C20 C19 N5 B3 -176.7(8) . . . . ?
C20 C19 N5 C22 0.2(10) . . . . ?
C20 C21 C22 C23 -179.9(7) . . . . ?
C20 C21 C22 N5 0.0(9) . . . . ?
C21 C22 C23 C24 -178.0(7) . . . . ?
C21 C22 C23 C32 -0.5(11) . . . . ?
C21 C22 N5 B3 176.8(7) . . . . ?
C21 C22 N5 C19 -0.1(8) . . . . ?
C22 C23 C24 C25 -177.5(7) . . . . ?
C22 C23 C24 N6 1.6(9) . . . . ?
C22 C23 C32 C31 55.4(9) . . . . ?
C22 C23 C32 C33 -126.2(7) . . . . ?
C23 C22 N5 B3 -3.3(10) . . . . ?
C23 C22 N5 C19 179.8(7) . . . . ?
C23 C24 C25 C26 -178.7(7) . . . . ?
C23 C24 N6 B3 -4.4(10) . . . . ?
C23 C24 N6 C27 179.7(6) . . . . ?
C23 C32 C33 C28 -179.7(6) . . . . ?
C24 C23 C32 C31 -127.0(7) . . . . ?
C24 C23 C32 C33 51.4(9) . . . . ?
C24 C25 C26 C27 -2.2(8) . . . . ?
C25 C24 N6 B3 174.9(6) . . . . ?
C25 C24 N6 C27 -1.0(7) . . . . ?
C25 C26 C27 N6 1.7(9) . . . . ?
C26 C27 N6 B3 -176.3(7) . . . . ?
C26 C27 N6 C24 -0.4(8) . . . . ?
C28 C5 C6 C7 6.1(10) . . . . ?
C28 C5 C6 N2 -177.7(5) . . . . ?
C28 C29 C30 C14 -178.7(6) . . . . ?
C28 C29 C30 C31 -0.2(10) . . . . ?
C29 C28 C33 C32 -0.8(10) . . . . ?
C29 C30 C31 C32 -1.9(10) . . . . ?
C30 C14 C15 C16 -3.7(12) . . . . ?
C30 C14 C15 N4 177.6(6) . . . . ?
C30 C31 C32 C23 -179.0(6) . . . . ?
C30 C31 C32 C33 2.6(10) . . . . ?
C31 C32 C33 C28 -1.3(10) . . . . ?
C32 C23 C24 C25 4.9(10) . . . . ?
C32 C23 C24 N6 -176.0(5) . . . . ?
C33 C28 C29 C30 1.6(10) . . . . ?
F1 B1 N1 C1 -67.1(8) . . . . ?
F1 B1 N1 C4 116.2(6) . . . . ?
F1 B1 N2 C6 -115.5(6) . . . . ?
F1 B1 N2 C9 59.8(8) . . . . ?
F2 B1 N1 C1 50.6(7) . . . . ?
F2 B1 N1 C4 -126.1(6) . . . . ?
F2 B1 N2 C6 125.1(6) . . . . ?
F2 B1 N2 C9 -59.6(8) . . . . ?
F3 B2 N3 C10 -71.9(10) . . . . ?
F3 B2 N3 C13 108.1(7) . . . . ?
F3 B2 N4 C15 -107.7(8) . . . . ?
F3 B2 N4 C18 66.5(12) . . . . ?
F4 B2 N3 C10 50.6(10) . . . . ?
F4 B2 N3 C13 -129.4(7) . . . . ?
F4 B2 N4 C15 130.9(7) . . . . ?
F4 B2 N4 C18 -54.9(12) . . . . ?
F5 B3 N5 C19 -64.0(10) . . . . ?
F5 B3 N5 C22 119.6(7) . . . . ?
F5 B3 N6 C24 -114.6(7) . . . . ?
F5 B3 N6 C27 60.5(9) . . . . ?
F6 B3 N5 C19 54.3(11) . . . . ?
F6 B3 N5 C22 -122.0(7) . . . . ?
F6 B3 N6 C24 126.3(7) . . . . ?
F6 B3 N6 C27 -58.7(10) . . . . ?
N1 B1 N2 C6 5.1(8) . . . . ?
N1 B1 N2 C9 -179.6(6) . . . . ?
N1 C1 C2 C3 -0.3(8) . . . . ?
N1 C4 C5 C6 0.4(9) . . . . ?
N1 C4 C5 C28 178.0(5) . . . . ?
N2 B1 N1 C1 172.0(6) . . . . ?
N2 B1 N1 C4 -4.8(8) . . . . ?
N2 C6 C7 C8 1.7(7) . . . . ?
N3 B2 N4 C15 12.5(10) . . . . ?
N3 B2 N4 C18 -173.3(9) . . . . ?
N3 C10 C11 C12 0.4(9) . . . . ?
N3 C13 C14 C15 2.8(10) . . . . ?
N3 C13 C14 C30 -175.8(6) . . . . ?
N4 B2 N3 C10 169.2(7) . . . . ?
N4 B2 N3 C13 -10.8(10) . . . . ?
N4 C15 C16 C17 0.7(10) . . . . ?
N5 B3 N6 C24 3.1(9) . . . . ?
N5 B3 N6 C27 178.1(7) . . . . ?
N5 C19 C20 C21 -0.2(12) . . . . ?
N5 C22 C23 C24 2.1(9) . . . . ?
N5 C22 C23 C32 179.6(6) . . . . ?
N6 B3 N5 C19 177.1(8) . . . . ?
N6 B3 N5 C22 0.8(9) . . . . ?
N6 C24 C25 C26 2.1(8) . . . . ?

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.467(4)
2 0.533(4)

