# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_HPIB1
_database_code_depnum_ccdc_archive 'CCDC 1945394'
loop_
_audit_author_name
_audit_author_address
'Bhupendra Kumar Dwivedi'
;Banaras Hindu University, India
India
;
_audit_update_record             
;
2019-08-05 deposited with the CCDC.	2019-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H24 B F2 N4 O'
_chemical_formula_sum            'C36 H24 B F2 N4 O'
_chemical_formula_weight         577.40

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'
N N 0.0061 0.0033 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.208(2)
_cell_length_b                   10.769(2)
_cell_length_c                   14.485(3)
_cell_angle_alpha                111.348(5)
_cell_angle_beta                 90.210(5)
_cell_angle_gamma                97.478(5)
_cell_volume                     1468.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2980
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      25.15

_exptl_crystal_description       Needle
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             598
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32481
_diffrn_reflns_av_unetI/netI     0.2352
_diffrn_reflns_av_R_equivalents  0.1605
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.024
_diffrn_reflns_theta_max         27.661
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             6599
_reflns_number_gt                2314
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0627P)²+1.3518P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6599
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3119
_refine_ls_R_factor_gt           0.1069
_refine_ls_wR_factor_ref         0.2264
_refine_ls_wR_factor_gt          0.1635
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.011

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
N3 N 0.2237(3) 0.2624(3) 0.4492(3) 0.0416(9) Uani 1 1 d . . . . .
F2 F 0.3271(4) -0.4406(3) -0.0694(3) 0.1173(14) Uani 1 1 d . . . . .
F1 F 0.2318(4) -0.4704(3) 0.0616(3) 0.1260(15) Uani 1 1 d . . . . .
N1 N 0.3978(4) -0.2814(4) 0.0930(3) 0.0543(11) Uani 1 1 d . . . . .
N4 N 0.2618(3) 0.4722(3) 0.4578(3) 0.0411(9) Uani 1 1 d . . . . .
C22 C 0.0534(5) 0.1498(6) 0.7379(4) 0.0642(15) Uani 1 1 d . . . . .
H22 H 0.020109 0.106612 0.779713 0.077 Uiso 1 1 calc R U . . .
C21 C 0.0812(6) 0.0769(5) 0.6440(4) 0.0758(17) Uani 1 1 d . . . . .
H21 H 0.068801 -0.016629 0.621593 0.091 Uiso 1 1 calc R U . . .
C20 C 0.1280(6) 0.1414(5) 0.5816(4) 0.0704(16) Uani 1 1 d . . . . .
H20 H 0.146021 0.090393 0.516978 0.085 Uiso 1 1 calc R U . . .
C19 C 0.1488(4) 0.2800(4) 0.6131(3) 0.0391(11) Uani 1 1 d . . . . .
C17 C 0.1964(4) 0.3436(4) 0.5434(3) 0.0409(11) Uani 1 1 d . . . . .
C16 C 0.2617(4) 0.3398(4) 0.3985(3) 0.0411(11) Uani 1 1 d . . . . .
C12 C 0.2976(4) 0.2800(4) 0.2945(3) 0.0364(11) Uani 1 1 d . . . . .
C11 C 0.2943(4) 0.1395(4) 0.2533(3) 0.0416(11) Uani 1 1 d . . . . .
C10 C 0.3235(4) 0.0743(4) 0.1547(3) 0.0404(11) Uani 1 1 d . . . . .
C5 C 0.3119(4) -0.0761(4) 0.1134(3) 0.0395(11) Uani 1 1 d . . . . .
C6 C 0.1959(4) -0.1495(4) 0.0585(3) 0.0434(12) Uani 1 1 d . . . . .
N2 N 0.1784(4) -0.2894(4) 0.0175(3) 0.0512(10) Uani 1 1 d . . . . .
C9 C 0.0569(5) -0.3307(5) -0.0262(4) 0.0617(14) Uani 1 1 d . . . . .
H9 H 0.020956 -0.420085 -0.060030 0.074 Uiso 1 1 calc R U . . .
C4 C 0.4112(4) -0.1418(4) 0.1299(3) 0.0451(12) Uani 1 1 d . . . . .
C31 C 0.3013(4) 0.5919(4) 0.4354(3) 0.0410(11) Uani 1 1 d . . . . .
C36 C 0.4278(5) 0.6564(5) 0.4582(4) 0.0691(16) Uani 1 1 d . . . . .
H36 H 0.489164 0.622402 0.486789 0.083 Uiso 1 1 calc R U . . .
C35 C 0.4646(6) 0.7703(6) 0.4392(5) 0.093(2) Uani 1 1 d . . . . .
H35 H 0.550941 0.814237 0.455089 0.111 Uiso 1 1 calc R U . . .
C34 C 0.3752(7) 0.8206(5) 0.3968(5) 0.0812(18) Uani 1 1 d . . . . .
H34 H 0.400629 0.898561 0.383882 0.097 Uiso 1 1 calc R U . . .
C33 C 0.2494(6) 0.7563(6) 0.3736(5) 0.0826(18) Uani 1 1 d . . . . .
H33 H 0.188612 0.789643 0.344068 0.099 Uiso 1 1 calc R U . . .
C32 C 0.2118(5) 0.6422(5) 0.3936(4) 0.0682(16) Uani 1 1 d . . . . .
H32 H 0.125028 0.598996 0.378727 0.082 Uiso 1 1 calc R U . . .
C18 C 0.2195(4) 0.4757(4) 0.5508(3) 0.0409(11) Uani 1 1 d . . . . .
C25 C 0.2065(4) 0.6017(4) 0.6336(3) 0.0418(11) Uani 1 1 d . . . . .
C30 C 0.0998(5) 0.6683(5) 0.6353(4) 0.0543(13) Uani 1 1 d . . . . .
H30 H 0.037330 0.635399 0.582124 0.065 Uiso 1 1 calc R U . . .
C29 C 0.0844(5) 0.7839(5) 0.7154(4) 0.0648(15) Uani 1 1 d . . . . .
H29 H 0.011247 0.827474 0.716192 0.078 Uiso 1 1 calc R U . . .
C28 C 0.1766(6) 0.8336(5) 0.7929(4) 0.0640(15) Uani 1 1 d . . . . .
H28 H 0.166367 0.911561 0.846408 0.077 Uiso 1 1 calc R U . . .
C27 C 0.2836(6) 0.7699(5) 0.7926(4) 0.0689(16) Uani 1 1 d . . . . .
H27 H 0.346230 0.804603 0.845772 0.083 Uiso 1 1 calc R U . . .
C26 C 0.2995(5) 0.6528(5) 0.7128(4) 0.0587(14) Uani 1 1 d . . . . .
H26 H 0.372419 0.609172 0.712775 0.070 Uiso 1 1 calc R U . . .
C23 C 0.0740(5) 0.2850(5) 0.7704(4) 0.0721(16) Uani 1 1 d . . . . .
H23 H 0.055385 0.334627 0.835138 0.087 Uiso 1 1 calc R U . . .
C24 C 0.1220(5) 0.3513(5) 0.7100(4) 0.0603(14) Uani 1 1 d . . . . .
H24 H 0.136647 0.444983 0.734539 0.072 Uiso 1 1 calc R U . . .
C13 C 0.3330(4) 0.3520(4) 0.2327(3) 0.0493(12) Uani 1 1 d . . . . .
H13 H 0.336592 0.445139 0.258060 0.059 Uiso 1 1 calc R U . . .
C14 C 0.3624(5) 0.2884(5) 0.1357(4) 0.0561(13) Uani 1 1 d . . . . .
H14 H 0.386151 0.338812 0.096578 0.067 Uiso 1 1 calc R U . . .
C15 C 0.3569(4) 0.1499(4) 0.0959(3) 0.0491(12) Uani 1 1 d . . . . .
H15 H 0.375537 0.107262 0.029962 0.059 Uiso 1 1 calc R U . . .
O1 O 0.2608(3) 0.0578(3) 0.3044(2) 0.0613(10) Uani 1 1 d . . . . .
H1 H 0.245310 0.103292 0.361316 0.092 Uiso 1 1 calc R U . . .
C8 C -0.0074(5) -0.2213(6) -0.0138(4) 0.0677(15) Uani 1 1 d . . . . .
H8 H -0.093355 -0.224019 -0.036801 0.081 Uiso 1 1 calc R U . . .
C7 C 0.0789(5) -0.1074(5) 0.0388(3) 0.0523(13) Uani 1 1 d . . . . .
H7 H 0.062297 -0.018840 0.057691 0.063 Uiso 1 1 calc R U . . .
C3 C 0.5320(5) -0.0917(5) 0.1868(4) 0.0649(15) Uani 1 1 d . . . . .
H3 H 0.566262 -0.001851 0.220803 0.078 Uiso 1 1 calc R U . . .
C2 C 0.5882(6) -0.2020(7) 0.1817(5) 0.0838(18) Uani 1 1 d . . . . .
H2 H 0.669314 -0.200555 0.211848 0.101 Uiso 1 1 calc R U . . .
C1 C 0.5048(6) -0.3160(6) 0.1245(5) 0.0766(17) Uani 1 1 d . . . . .
H1A H 0.521034 -0.403952 0.110066 0.092 Uiso 1 1 calc R U . . .
B1 B 0.2817(7) -0.3760(6) 0.0254(5) 0.0674(18) 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
N3 C16 1.321(5) . ?
N3 C17 1.379(5) . ?
F2 B1 1.407(7) . ?
F1 B1 1.350(7) . ?
N1 C1 1.329(6) . ?
N1 C4 1.388(5) . ?
N1 B1 1.534(7) . ?
N4 C16 1.371(5) . ?
N4 C18 1.405(5) . ?
N4 C31 1.449(5) . ?
C22 C23 1.344(6) . ?
C22 C21 1.352(7) . ?
C22 H22 0.9300 . ?
C21 C20 1.379(6) . ?
C21 H21 0.9300 . ?
C20 C19 1.380(6) . ?
C20 H20 0.9300 . ?
C19 C24 1.381(6) . ?
C19 C17 1.465(6) . ?
C17 C18 1.376(5) . ?
C16 C12 1.475(6) . ?
C12 C13 1.402(6) . ?
C12 C11 1.406(5) . ?
C11 O1 1.355(5) . ?
C11 C10 1.396(6) . ?
C10 C15 1.392(6) . ?
C10 C5 1.497(5) . ?
C5 C4 1.376(6) . ?
C5 C6 1.397(6) . ?
C6 N2 1.390(5) . ?
C6 C7 1.396(6) . ?
N2 C9 1.336(6) . ?
N2 B1 1.525(7) . ?
C9 C8 1.378(6) . ?
C9 H9 0.9300 . ?
C4 C3 1.408(6) . ?
C31 C36 1.362(6) . ?
C31 C32 1.363(6) . ?
C36 C35 1.360(6) . ?
C36 H36 0.9300 . ?
C35 C34 1.367(7) . ?
C35 H35 0.9300 . ?
C34 C33 1.355(7) . ?
C34 H34 0.9300 . ?
C33 C32 1.372(7) . ?
C33 H33 0.9300 . ?
C32 H32 0.9300 . ?
C18 C25 1.469(6) . ?
C25 C30 1.375(6) . ?
C25 C26 1.385(6) . ?
C30 C29 1.386(6) . ?
C30 H30 0.9300 . ?
C29 C28 1.363(7) . ?
C29 H29 0.9300 . ?
C28 C27 1.363(7) . ?
C28 H28 0.9300 . ?
C27 C26 1.396(6) . ?
C27 H27 0.9300 . ?
C26 H26 0.9300 . ?
C23 C24 1.371(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C13 C14 1.375(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
O1 H1 0.8200 . ?
C8 C7 1.377(6) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
C3 C2 1.364(6) . ?
C3 H3 0.9300 . ?
C2 C1 1.379(7) . ?
C2 H2 0.9300 . ?
C1 H1A 0.9300 . ?

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
C16 N3 C17 108.5(3) . . ?
C1 N1 C4 107.4(4) . . ?
C1 N1 B1 127.2(4) . . ?
C4 N1 B1 125.4(4) . . ?
C16 N4 C18 107.6(3) . . ?
C16 N4 C31 129.0(4) . . ?
C18 N4 C31 123.4(3) . . ?
C23 C22 C21 119.7(5) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C21 C20 120.0(5) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C20 C19 121.3(5) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C19 C24 117.2(4) . . ?
C20 C19 C17 119.2(4) . . ?
C24 C19 C17 123.6(4) . . ?
C18 C17 N3 108.7(4) . . ?
C18 C17 C19 132.7(4) . . ?
N3 C17 C19 118.7(4) . . ?
N3 C16 N4 109.5(4) . . ?
N3 C16 C12 120.6(4) . . ?
N4 C16 C12 129.9(4) . . ?
C13 C12 C11 117.2(4) . . ?
C13 C12 C16 125.2(4) . . ?
C11 C12 C16 117.6(4) . . ?
O1 C11 C10 115.3(4) . . ?
O1 C11 C12 123.3(4) . . ?
C10 C11 C12 121.4(4) . . ?
C15 C10 C11 119.4(4) . . ?
C15 C10 C5 121.5(4) . . ?
C11 C10 C5 119.0(4) . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 C10 121.4(4) . . ?
C6 C5 C10 118.3(4) . . ?
N2 C6 C7 107.6(4) . . ?
N2 C6 C5 121.5(4) . . ?
C7 C6 C5 130.8(4) . . ?
C9 N2 C6 107.8(4) . . ?
C9 N2 B1 127.8(4) . . ?
C6 N2 B1 124.4(4) . . ?
N2 C9 C8 110.0(4) . . ?
N2 C9 H9 125.0 . . ?
C8 C9 H9 125.0 . . ?
C5 C4 N1 120.8(4) . . ?
C5 C4 C3 130.9(4) . . ?
N1 C4 C3 108.2(4) . . ?
C36 C31 C32 119.8(4) . . ?
C36 C31 N4 119.9(4) . . ?
C32 C31 N4 120.3(4) . . ?
C35 C36 C31 120.0(5) . . ?
C35 C36 H36 120.0 . . ?
C31 C36 H36 120.0 . . ?
C36 C35 C34 120.4(5) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C33 C34 C35 119.7(5) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C34 C33 C32 120.1(5) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C31 C32 C33 120.1(5) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C17 C18 N4 105.7(4) . . ?
C17 C18 C25 131.3(4) . . ?
N4 C18 C25 122.9(4) . . ?
C30 C25 C26 118.9(4) . . ?
C30 C25 C18 120.7(4) . . ?
C26 C25 C18 120.3(4) . . ?
C25 C30 C29 120.8(5) . . ?
C25 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C28 C29 C30 119.9(5) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C29 C28 C27 120.4(5) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C27 C26 120.1(5) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C25 C26 C27 119.8(5) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C22 C23 C24 121.4(5) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C19 120.4(5) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C14 C13 C12 121.7(4) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 120.3(4) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.0(4) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C11 O1 H1 109.5 . . ?
C7 C8 C9 107.4(5) . . ?
C7 C8 H8 126.3 . . ?
C9 C8 H8 126.3 . . ?
C8 C7 C6 107.2(4) . . ?
C8 C7 H7 126.4 . . ?
C6 C7 H7 126.4 . . ?
C2 C3 C4 105.9(5) . . ?
C2 C3 H3 127.1 . . ?
C4 C3 H3 127.1 . . ?
C3 C2 C1 108.6(5) . . ?
C3 C2 H2 125.7 . . ?
C1 C2 H2 125.7 . . ?
N1 C1 C2 109.8(5) . . ?
N1 C1 H1A 125.1 . . ?
C2 C1 H1A 125.1 . . ?
F1 B1 F2 108.8(5) . . ?
F1 B1 N2 111.9(5) . . ?
F2 B1 N2 109.1(5) . . ?
F1 B1 N1 110.8(5) . . ?
F2 B1 N1 108.9(5) . . ?
N2 B1 N1 107.4(4) . . ?

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
C23 C22 C21 C20 -1.3(9) . . . . ?
C22 C21 C20 C19 0.7(9) . . . . ?
C21 C20 C19 C24 0.7(8) . . . . ?
C21 C20 C19 C17 -178.9(5) . . . . ?
C16 N3 C17 C18 -0.5(5) . . . . ?
C16 N3 C17 C19 178.5(4) . . . . ?
C20 C19 C17 C18 176.2(5) . . . . ?
C24 C19 C17 C18 -3.3(8) . . . . ?
C20 C19 C17 N3 -2.4(6) . . . . ?
C24 C19 C17 N3 178.0(4) . . . . ?
C17 N3 C16 N4 0.7(5) . . . . ?
C17 N3 C16 C12 -180.0(4) . . . . ?
C18 N4 C16 N3 -0.7(4) . . . . ?
C31 N4 C16 N3 177.2(4) . . . . ?
C18 N4 C16 C12 -179.9(4) . . . . ?
C31 N4 C16 C12 -2.0(7) . . . . ?
N3 C16 C12 C13 176.8(4) . . . . ?
N4 C16 C12 C13 -4.1(7) . . . . ?
N3 C16 C12 C11 -2.2(6) . . . . ?
N4 C16 C12 C11 177.0(4) . . . . ?
C13 C12 C11 O1 -179.5(4) . . . . ?
C16 C12 C11 O1 -0.5(6) . . . . ?
C13 C12 C11 C10 -0.7(6) . . . . ?
C16 C12 C11 C10 178.4(4) . . . . ?
O1 C11 C10 C15 179.0(4) . . . . ?
C12 C11 C10 C15 0.1(6) . . . . ?
O1 C11 C10 C5 1.9(6) . . . . ?
C12 C11 C10 C5 -177.0(4) . . . . ?
C15 C10 C5 C4 101.3(5) . . . . ?
C11 C10 C5 C4 -81.6(5) . . . . ?
C15 C10 C5 C6 -79.7(5) . . . . ?
C11 C10 C5 C6 97.3(5) . . . . ?
C4 C5 C6 N2 -1.4(6) . . . . ?
C10 C5 C6 N2 179.7(4) . . . . ?
C4 C5 C6 C7 174.2(5) . . . . ?
C10 C5 C6 C7 -4.7(7) . . . . ?
C7 C6 N2 C9 0.7(5) . . . . ?
C5 C6 N2 C9 177.2(4) . . . . ?
C7 C6 N2 B1 -177.9(5) . . . . ?
C5 C6 N2 B1 -1.5(7) . . . . ?
C6 N2 C9 C8 -0.9(5) . . . . ?
B1 N2 C9 C8 177.7(5) . . . . ?
C6 C5 C4 N1 -0.3(6) . . . . ?
C10 C5 C4 N1 178.6(4) . . . . ?
C6 C5 C4 C3 -175.8(5) . . . . ?
C10 C5 C4 C3 3.1(7) . . . . ?
C1 N1 C4 C5 -176.9(4) . . . . ?
B1 N1 C4 C5 5.0(7) . . . . ?
C1 N1 C4 C3 -0.5(5) . . . . ?
B1 N1 C4 C3 -178.6(5) . . . . ?
C16 N4 C31 C36 -92.6(6) . . . . ?
C18 N4 C31 C36 85.0(5) . . . . ?
C16 N4 C31 C32 88.8(6) . . . . ?
C18 N4 C31 C32 -93.6(5) . . . . ?
C32 C31 C36 C35 -0.1(8) . . . . ?
N4 C31 C36 C35 -178.7(5) . . . . ?
C31 C36 C35 C34 -0.3(9) . . . . ?
C36 C35 C34 C33 0.0(10) . . . . ?
C35 C34 C33 C32 0.7(10) . . . . ?
C36 C31 C32 C33 0.7(8) . . . . ?
N4 C31 C32 C33 179.3(5) . . . . ?
C34 C33 C32 C31 -1.1(9) . . . . ?
N3 C17 C18 N4 0.1(4) . . . . ?
C19 C17 C18 N4 -178.7(4) . . . . ?
N3 C17 C18 C25 180.0(4) . . . . ?
C19 C17 C18 C25 1.3(8) . . . . ?
C16 N4 C18 C17 0.4(4) . . . . ?
C31 N4 C18 C17 -177.7(4) . . . . ?
C16 N4 C18 C25 -179.6(4) . . . . ?
C31 N4 C18 C25 2.4(6) . . . . ?
C17 C18 C25 C30 -102.6(6) . . . . ?
N4 C18 C25 C30 77.3(5) . . . . ?
C17 C18 C25 C26 75.3(6) . . . . ?
N4 C18 C25 C26 -104.8(5) . . . . ?
C26 C25 C30 C29 -0.8(7) . . . . ?
C18 C25 C30 C29 177.2(4) . . . . ?
C25 C30 C29 C28 0.9(7) . . . . ?
C30 C29 C28 C27 -0.4(8) . . . . ?
C29 C28 C27 C26 -0.1(8) . . . . ?
C30 C25 C26 C27 0.2(7) . . . . ?
C18 C25 C26 C27 -177.8(4) . . . . ?
C28 C27 C26 C25 0.3(7) . . . . ?
C21 C22 C23 C24 0.5(9) . . . . ?
C22 C23 C24 C19 0.9(8) . . . . ?
C20 C19 C24 C23 -1.5(7) . . . . ?
C17 C19 C24 C23 178.1(5) . . . . ?
C11 C12 C13 C14 0.4(6) . . . . ?
C16 C12 C13 C14 -178.6(4) . . . . ?
C12 C13 C14 C15 0.4(7) . . . . ?
C13 C14 C15 C10 -1.0(7) . . . . ?
C11 C10 C15 C14 0.8(7) . . . . ?
C5 C10 C15 C14 177.8(4) . . . . ?
N2 C9 C8 C7 0.8(6) . . . . ?
C9 C8 C7 C6 -0.3(6) . . . . ?
N2 C6 C7 C8 -0.2(5) . . . . ?
C5 C6 C7 C8 -176.2(5) . . . . ?
C5 C4 C3 C2 176.5(5) . . . . ?
N1 C4 C3 C2 0.6(6) . . . . ?
C4 C3 C2 C1 -0.4(6) . . . . ?
C4 N1 C1 C2 0.2(6) . . . . ?
B1 N1 C1 C2 178.3(5) . . . . ?
C3 C2 C1 N1 0.1(7) . . . . ?
C9 N2 B1 F1 -51.6(7) . . . . ?
C6 N2 B1 F1 126.8(5) . . . . ?
C9 N2 B1 F2 68.8(7) . . . . ?
C6 N2 B1 F2 -112.9(5) . . . . ?
C9 N2 B1 N1 -173.4(4) . . . . ?
C6 N2 B1 N1 5.0(7) . . . . ?
C1 N1 B1 F1 53.0(8) . . . . ?
C4 N1 B1 F1 -129.2(5) . . . . ?
C1 N1 B1 F2 -66.6(7) . . . . ?
C4 N1 B1 F2 111.2(5) . . . . ?
C1 N1 B1 N2 175.4(5) . . . . ?
C4 N1 B1 N2 -6.8(7) . . . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_HPIB3
_database_code_depnum_ccdc_archive 'CCDC 1945396'
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2019-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H26 B Cl F2 N4 O'
_chemical_formula_sum            'C37 H26 B Cl F2 N4 O'
_chemical_formula_weight         626.88

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'
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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1437(2)
_cell_length_b                   14.2235(3)
_cell_length_c                   24.9508(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.853(2)
_cell_angle_gamma                90
_cell_volume                     3214.55(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4125
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      25.17

_exptl_crystal_description       Needle
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.167
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47535
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.969
_diffrn_reflns_theta_max         32.277
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             10674
_reflns_number_gt                6044
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0753P)²+0.4492P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0029(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10674
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1815
_refine_ls_wR_factor_gt          0.1463
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl1 Cl 0.96737(8) 0.84492(4) 0.40097(2) 0.0883(2) Uani 1 1 d . . . . .
F1 F 0.42800(13) 0.46039(9) 0.17170(5) 0.0721(3) Uani 1 1 d . . . . .
F2 F 0.57570(15) 0.52856(9) 0.11752(4) 0.0727(3) Uani 1 1 d . . . . .
B1 B 0.5493(2) 0.51786(15) 0.17017(8) 0.0521(5) Uani 1 1 d . . . . .
O1 O 0.67542(14) 0.47862(8) 0.36954(5) 0.0525(3) Uani 1 1 d . . . . .
H38 H 0.675364 0.450252 0.399069 0.079 Uiso 1 1 calc R U . . .
N2 N 0.52448(17) 0.61494(11) 0.19541(6) 0.0510(4) Uani 1 1 d . . . . .
N1 N 0.68566(16) 0.47562(10) 0.20556(6) 0.0495(3) Uani 1 1 d . . . . .
N4 N 0.78472(16) 0.55839(9) 0.53151(5) 0.0439(3) Uani 1 1 d . . . . .
N3 N 0.71902(16) 0.44817(10) 0.47041(5) 0.0480(3) Uani 1 1 d . . . . .
C9 C 0.4326(2) 0.68319(16) 0.17399(8) 0.0654(5) Uani 1 1 d . . . . .
H9 H 0.379398 0.681984 0.138526 0.079 Uiso 1 1 calc R U . . .
C8 C 0.4264(2) 0.75560(15) 0.21091(9) 0.0669(5) Uani 1 1 d . . . . .
H8 H 0.370122 0.811733 0.205203 0.080 Uiso 1 1 calc R U . . .
C7 C 0.5170(2) 0.73078(13) 0.25722(8) 0.0563(4) Uani 1 1 d . . . . .
H7 H 0.533439 0.766064 0.289813 0.068 Uiso 1 1 calc R U . . .
C6 C 0.58116(19) 0.64315(12) 0.24752(7) 0.0460(4) Uani 1 1 d . . . . .
C5 C 0.68964(18) 0.58897(11) 0.27834(6) 0.0421(3) Uani 1 1 d . . . . .
C4 C 0.74512(19) 0.50808(12) 0.25655(6) 0.0449(4) Uani 1 1 d . . . . .
C3 C 0.8680(2) 0.45141(13) 0.27536(8) 0.0532(4) Uani 1 1 d . . . . .
H3 H 0.929884 0.457345 0.309013 0.064 Uiso 1 1 calc R U . . .
C2 C 0.8812(2) 0.38610(15) 0.23586(9) 0.0649(5) Uani 1 1 d . . . . .
H2 H 0.954470 0.338500 0.237045 0.078 Uiso 1 1 calc R U . . .
C1 C 0.7677(2) 0.40228(14) 0.19374(8) 0.0608(5) Uani 1 1 d . . . . .
H1 H 0.750820 0.366552 0.161311 0.073 Uiso 1 1 calc R U . . .
C10 C 0.75174(18) 0.62072(11) 0.33382(6) 0.0423(3) Uani 1 1 d . . . . .
C15 C 0.81832(19) 0.70867(12) 0.34113(7) 0.0482(4) Uani 1 1 d . . . . .
H15 H 0.823157 0.748737 0.310960 0.058 Uiso 1 1 calc R U . . .
C14 C 0.8773(2) 0.73741(12) 0.39244(7) 0.0519(4) Uani 1 1 d . . . . .
C13 C 0.8673(2) 0.68213(12) 0.43717(7) 0.0504(4) Uani 1 1 d . . . . .
H13 H 0.909732 0.703160 0.471979 0.060 Uiso 1 1 calc R U . . .
C12 C 0.79483(18) 0.59515(11) 0.43167(6) 0.0424(3) Uani 1 1 d . . . . .
C11 C 0.74113(17) 0.56274(11) 0.37864(6) 0.0415(3) Uani 1 1 d . . . . .
C16 C 0.76851(19) 0.53570(12) 0.47750(6) 0.0441(4) Uani 1 1 d . . . . .
C18 C 0.74318(18) 0.47969(12) 0.55939(6) 0.0448(4) Uani 1 1 d . . . . .
C17 C 0.70221(19) 0.41260(12) 0.52051(7) 0.0465(4) Uani 1 1 d . . . . .
C31 C 0.83542(18) 0.64520(11) 0.55757(6) 0.0419(3) Uani 1 1 d . . . . .
C36 C 0.7440(2) 0.72222(13) 0.55416(8) 0.0550(4) Uani 1 1 d . . . . .
H36 H 0.648062 0.719079 0.534064 0.066 Uiso 1 1 calc R U . . .
C35 C 0.7930(2) 0.80426(15) 0.58027(9) 0.0682(6) Uani 1 1 d . . . . .
H35 H 0.730313 0.857813 0.577579 0.082 Uiso 1 1 calc R U . . .
C34 C 0.9317(3) 0.80997(16) 0.61030(9) 0.0693(6) Uani 1 1 d . . . . .
C33 C 1.0210(2) 0.73066(15) 0.61352(9) 0.0643(5) Uani 1 1 d . . . . .
H33 H 1.115933 0.732886 0.634390 0.077 Uiso 1 1 calc R U . . .
C32 C 0.9743(2) 0.64868(13) 0.58696(7) 0.0508(4) Uani 1 1 d . . . . .
H32 H 1.037181 0.595265 0.588915 0.061 Uiso 1 1 calc R U . . .
C25 C 0.75023(18) 0.47648(12) 0.61875(6) 0.0455(4) Uani 1 1 d . . . . .
C30 C 0.6852(2) 0.54417(14) 0.64771(7) 0.0564(4) Uani 1 1 d . . . . .
H30 H 0.636183 0.596095 0.629216 0.068 Uiso 1 1 calc R U . . .
C29 C 0.6907(2) 0.53697(16) 0.70328(8) 0.0654(5) Uani 1 1 d . . . . .
H29 H 0.646490 0.584222 0.722656 0.078 Uiso 1 1 calc R U . . .
C28 C 0.7596(2) 0.46220(17) 0.73044(8) 0.0645(5) Uani 1 1 d . . . . .
H28 H 0.763075 0.457468 0.768571 0.077 Uiso 1 1 calc R U . . .
C27 C 0.8243(2) 0.39344(16) 0.70223(8) 0.0643(5) Uani 1 1 d . . . . .
H27 H 0.871401 0.341185 0.721014 0.077 Uiso 1 1 calc R U . . .
C26 C 0.8206(2) 0.40056(14) 0.64676(7) 0.0536(4) Uani 1 1 d . . . . .
H26 H 0.866207 0.353535 0.627663 0.064 Uiso 1 1 calc R U . . .
C19 C 0.6470(2) 0.31616(12) 0.52570(7) 0.0494(4) Uani 1 1 d . . . . .
C24 C 0.5600(2) 0.29141(14) 0.56538(8) 0.0564(4) Uani 1 1 d . . . . .
H24 H 0.535898 0.337248 0.590447 0.068 Uiso 1 1 calc R U . . .
C23 C 0.5089(3) 0.20011(17) 0.56822(9) 0.0725(6) Uani 1 1 d . . . . .
H23 H 0.450492 0.183671 0.595504 0.087 Uiso 1 1 calc R U . . .
C22 C 0.5415(3) 0.13340(16) 0.53225(10) 0.0825(7) Uani 1 1 d . . . . .
H22 H 0.505984 0.070975 0.534635 0.099 Uiso 1 1 calc R U . . .
C21 C 0.6253(3) 0.15670(15) 0.49279(10) 0.0852(8) Uani 1 1 d . . . . .
H21 H 0.646730 0.110559 0.467463 0.102 Uiso 1 1 calc R U . . .
C20 C 0.6790(3) 0.24724(14) 0.48964(8) 0.0669(5) Uani 1 1 d . . . . .
H20 H 0.738465 0.262406 0.462481 0.080 Uiso 1 1 calc R U . . .
C37 C 0.9831(4) 0.9008(2) 0.63908(15) 0.1244(13) Uani 1 1 d . . . . .
H37A H 0.918034 0.952416 0.624961 0.187 Uiso 1 1 calc R U . . .
H37B H 1.084424 0.914594 0.632828 0.187 Uiso 1 1 calc R U . . .
H37C H 0.980059 0.893839 0.677985 0.187 Uiso 1 1 calc R U . . .


_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
Cl1 C14 1.7359(18) . ?
F1 B1 1.382(2) . ?
F2 B1 1.376(2) . ?
B1 N2 1.547(3) . ?
B1 N1 1.548(3) . ?
O1 C11 1.3441(19) . ?
O1 H38 0.8400 . ?
N2 C9 1.346(2) . ?
N2 C6 1.391(2) . ?
N1 C1 1.341(2) . ?
N1 C4 1.392(2) . ?
N4 C16 1.3740(19) . ?
N4 C18 1.398(2) . ?
N4 C31 1.442(2) . ?
N3 C16 1.328(2) . ?
N3 C17 1.377(2) . ?
C9 C8 1.388(3) . ?
C9 H9 0.9500 . ?
C8 C7 1.372(3) . ?
C8 H8 0.9500 . ?
C7 C6 1.413(2) . ?
C7 H7 0.9500 . ?
C6 C5 1.400(2) . ?
C5 C4 1.397(2) . ?
C5 C10 1.493(2) . ?
C4 C3 1.410(2) . ?
C3 C2 1.372(3) . ?
C3 H3 0.9500 . ?
C2 C1 1.392(3) . ?
C2 H2 0.9500 . ?
C1 H1 0.9500 . ?
C10 C15 1.392(2) . ?
C10 C11 1.403(2) . ?
C15 C14 1.381(2) . ?
C15 H15 0.9500 . ?
C14 C13 1.379(2) . ?
C13 C12 1.401(2) . ?
C13 H13 0.9500 . ?
C12 C11 1.424(2) . ?
C12 C16 1.468(2) . ?
C18 C17 1.376(2) . ?
C18 C25 1.474(2) . ?
C17 C19 1.474(2) . ?
C31 C36 1.374(2) . ?
C31 C32 1.378(2) . ?
C36 C35 1.381(3) . ?
C36 H36 0.9500 . ?
C35 C34 1.384(3) . ?
C35 H35 0.9500 . ?
C34 C33 1.388(3) . ?
C34 C37 1.521(3) . ?
C33 C32 1.380(3) . ?
C33 H33 0.9500 . ?
C32 H32 0.9500 . ?
C25 C30 1.386(2) . ?
C25 C26 1.395(2) . ?
C30 C29 1.384(3) . ?
C30 H30 0.9500 . ?
C29 C28 1.368(3) . ?
C29 H29 0.9500 . ?
C28 C27 1.384(3) . ?
C28 H28 0.9500 . ?
C27 C26 1.383(3) . ?
C27 H27 0.9500 . ?
C26 H26 0.9500 . ?
C19 C20 1.389(3) . ?
C19 C24 1.397(3) . ?
C24 C23 1.385(3) . ?
C24 H24 0.9500 . ?
C23 C22 1.367(4) . ?
C23 H23 0.9500 . ?
C22 C21 1.369(4) . ?
C22 H22 0.9500 . ?
C21 C20 1.384(3) . ?
C21 H21 0.9500 . ?
C20 H20 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?

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
F2 B1 F1 109.76(16) . . ?
F2 B1 N2 110.15(16) . . ?
F1 B1 N2 110.73(16) . . ?
F2 B1 N1 110.76(16) . . ?
F1 B1 N1 109.97(16) . . ?
N2 B1 N1 105.40(14) . . ?
C11 O1 H38 109.5 . . ?
C9 N2 C6 107.19(15) . . ?
C9 N2 B1 126.90(16) . . ?
C6 N2 B1 125.54(15) . . ?
C1 N1 C4 107.37(16) . . ?
C1 N1 B1 127.45(16) . . ?
C4 N1 B1 125.19(14) . . ?
C16 N4 C18 107.44(13) . . ?
C16 N4 C31 128.92(13) . . ?
C18 N4 C31 123.63(13) . . ?
C16 N3 C17 107.57(14) . . ?
N2 C9 C8 110.59(17) . . ?
N2 C9 H9 124.7 . . ?
C8 C9 H9 124.7 . . ?
C7 C8 C9 107.04(18) . . ?
C7 C8 H8 126.5 . . ?
C9 C8 H8 126.5 . . ?
C8 C7 C6 107.45(17) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
N2 C6 C5 119.99(15) . . ?
N2 C6 C7 107.70(15) . . ?
C5 C6 C7 132.17(16) . . ?
C4 C5 C6 120.47(15) . . ?
C4 C5 C10 119.85(15) . . ?
C6 C5 C10 119.60(14) . . ?
N1 C4 C5 120.76(15) . . ?
N1 C4 C3 107.97(15) . . ?
C5 C4 C3 131.02(16) . . ?
C2 C3 C4 107.00(17) . . ?
C2 C3 H3 126.5 . . ?
C4 C3 H3 126.5 . . ?
C3 C2 C1 107.51(18) . . ?
C3 C2 H2 126.2 . . ?
C1 C2 H2 126.2 . . ?
N1 C1 C2 110.15(17) . . ?
N1 C1 H1 124.9 . . ?
C2 C1 H1 124.9 . . ?
C15 C10 C11 120.02(15) . . ?
C15 C10 C5 119.83(14) . . ?
C11 C10 C5 120.15(14) . . ?
C14 C15 C10 119.72(15) . . ?
C14 C15 H15 120.1 . . ?
C10 C15 H15 120.1 . . ?
C13 C14 C15 121.37(16) . . ?
C13 C14 Cl1 119.09(14) . . ?
C15 C14 Cl1 119.54(14) . . ?
C14 C13 C12 120.49(16) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C12 C11 118.38(14) . . ?
C13 C12 C16 123.90(14) . . ?
C11 C12 C16 117.70(14) . . ?
O1 C11 C10 117.81(14) . . ?
O1 C11 C12 122.32(14) . . ?
C10 C11 C12 119.84(14) . . ?
N3 C16 N4 109.87(14) . . ?
N3 C16 C12 121.69(14) . . ?
N4 C16 C12 128.42(14) . . ?
C17 C18 N4 105.73(14) . . ?
C17 C18 C25 131.08(16) . . ?
N4 C18 C25 123.17(15) . . ?
C18 C17 N3 109.39(15) . . ?
C18 C17 C19 130.34(15) . . ?
N3 C17 C19 120.27(14) . . ?
C36 C31 C32 120.88(16) . . ?
C36 C31 N4 119.96(15) . . ?
C32 C31 N4 119.14(15) . . ?
C31 C36 C35 119.29(17) . . ?
C31 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
C36 C35 C34 121.27(19) . . ?
C36 C35 H35 119.4 . . ?
C34 C35 H35 119.4 . . ?
C35 C34 C33 118.15(18) . . ?
C35 C34 C37 120.4(2) . . ?
C33 C34 C37 121.4(2) . . ?
C32 C33 C34 121.19(18) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C31 C32 C33 119.22(17) . . ?
C31 C32 H32 120.4 . . ?
C33 C32 H32 120.4 . . ?
C30 C25 C26 118.57(16) . . ?
C30 C25 C18 122.64(16) . . ?
C26 C25 C18 118.76(16) . . ?
C29 C30 C25 120.74(18) . . ?
C29 C30 H30 119.6 . . ?
C25 C30 H30 119.6 . . ?
C28 C29 C30 120.35(19) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C28 C27 119.83(18) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C26 C27 C28 120.22(19) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C26 C25 120.29(18) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C20 C19 C24 118.17(17) . . ?
C20 C19 C17 119.67(16) . . ?
C24 C19 C17 122.14(17) . . ?
C23 C24 C19 120.1(2) . . ?
C23 C24 H24 120.0 . . ?
C19 C24 H24 120.0 . . ?
C22 C23 C24 120.8(2) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C22 C21 119.9(2) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C20 C19 120.8(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?

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
F2 B1 N2 C9 49.9(3) . . . . ?
F1 B1 N2 C9 -71.7(2) . . . . ?
N1 B1 N2 C9 169.38(18) . . . . ?
F2 B1 N2 C6 -138.06(18) . . . . ?
F1 B1 N2 C6 100.3(2) . . . . ?
N1 B1 N2 C6 -18.5(2) . . . . ?
F2 B1 N1 C1 -46.0(3) . . . . ?
F1 B1 N1 C1 75.5(2) . . . . ?
N2 B1 N1 C1 -165.09(17) . . . . ?
F2 B1 N1 C4 134.29(17) . . . . ?
F1 B1 N1 C4 -104.21(19) . . . . ?
N2 B1 N1 C4 15.2(2) . . . . ?
C6 N2 C9 C8 -0.4(2) . . . . ?
B1 N2 C9 C8 172.82(19) . . . . ?
N2 C9 C8 C7 -0.6(3) . . . . ?
C9 C8 C7 C6 1.4(2) . . . . ?
C9 N2 C6 C5 -175.01(17) . . . . ?
B1 N2 C6 C5 11.6(3) . . . . ?
C9 N2 C6 C7 1.3(2) . . . . ?
B1 N2 C6 C7 -172.11(17) . . . . ?
C8 C7 C6 N2 -1.6(2) . . . . ?
C8 C7 C6 C5 174.02(19) . . . . ?
N2 C6 C5 C4 2.0(2) . . . . ?
C7 C6 C5 C4 -173.18(19) . . . . ?
N2 C6 C5 C10 178.89(15) . . . . ?
C7 C6 C5 C10 3.7(3) . . . . ?
C1 N1 C4 C5 175.17(16) . . . . ?
B1 N1 C4 C5 -5.1(3) . . . . ?
C1 N1 C4 C3 0.3(2) . . . . ?
B1 N1 C4 C3 -179.97(16) . . . . ?
C6 C5 C4 N1 -5.2(2) . . . . ?
C10 C5 C4 N1 177.99(14) . . . . ?
C6 C5 C4 C3 168.42(18) . . . . ?
C10 C5 C4 C3 -8.4(3) . . . . ?
N1 C4 C3 C2 0.1(2) . . . . ?
C5 C4 C3 C2 -174.15(18) . . . . ?
C4 C3 C2 C1 -0.3(2) . . . . ?
C4 N1 C1 C2 -0.5(2) . . . . ?
B1 N1 C1 C2 179.76(18) . . . . ?
C3 C2 C1 N1 0.5(2) . . . . ?
C4 C5 C10 C15 119.26(18) . . . . ?
C6 C5 C10 C15 -57.6(2) . . . . ?
C4 C5 C10 C11 -61.7(2) . . . . ?
C6 C5 C10 C11 121.42(18) . . . . ?
C11 C10 C15 C14 1.8(3) . . . . ?
C5 C10 C15 C14 -179.21(16) . . . . ?
C10 C15 C14 C13 -2.3(3) . . . . ?
C10 C15 C14 Cl1 177.18(14) . . . . ?
C15 C14 C13 C12 -0.7(3) . . . . ?
Cl1 C14 C13 C12 179.77(14) . . . . ?
C14 C13 C12 C11 4.2(3) . . . . ?
C14 C13 C12 C16 -174.74(17) . . . . ?
C15 C10 C11 O1 179.75(15) . . . . ?
C5 C10 C11 O1 0.7(2) . . . . ?
C15 C10 C11 C12 1.8(2) . . . . ?
C5 C10 C11 C12 -177.26(15) . . . . ?
C13 C12 C11 O1 177.41(16) . . . . ?
C16 C12 C11 O1 -3.6(2) . . . . ?
C13 C12 C11 C10 -4.7(2) . . . . ?
C16 C12 C11 C10 174.30(15) . . . . ?
C17 N3 C16 N4 0.04(19) . . . . ?
C17 N3 C16 C12 -178.38(15) . . . . ?
C18 N4 C16 N3 0.28(19) . . . . ?
C31 N4 C16 N3 179.83(16) . . . . ?
C18 N4 C16 C12 178.56(17) . . . . ?
C31 N4 C16 C12 -1.9(3) . . . . ?
C13 C12 C16 N3 -170.02(17) . . . . ?
C11 C12 C16 N3 11.0(2) . . . . ?
C13 C12 C16 N4 11.9(3) . . . . ?
C11 C12 C16 N4 -167.06(16) . . . . ?
C16 N4 C18 C17 -0.48(18) . . . . ?
C31 N4 C18 C17 179.94(15) . . . . ?
C16 N4 C18 C25 178.10(15) . . . . ?
C31 N4 C18 C25 -1.5(2) . . . . ?
N4 C18 C17 N3 0.5(2) . . . . ?
C25 C18 C17 N3 -177.91(17) . . . . ?
N4 C18 C17 C19 -179.22(17) . . . . ?
C25 C18 C17 C19 2.4(3) . . . . ?
C16 N3 C17 C18 -0.4(2) . . . . ?
C16 N3 C17 C19 179.41(16) . . . . ?
C16 N4 C31 C36 75.4(2) . . . . ?
C18 N4 C31 C36 -105.1(2) . . . . ?
C16 N4 C31 C32 -106.5(2) . . . . ?
C18 N4 C31 C32 73.0(2) . . . . ?
C32 C31 C36 C35 0.5(3) . . . . ?
N4 C31 C36 C35 178.66(18) . . . . ?
C31 C36 C35 C34 -0.8(3) . . . . ?
C36 C35 C34 C33 0.0(4) . . . . ?
C36 C35 C34 C37 -179.6(3) . . . . ?
C35 C34 C33 C32 1.0(4) . . . . ?
C37 C34 C33 C32 -179.4(3) . . . . ?
C36 C31 C32 C33 0.5(3) . . . . ?
N4 C31 C32 C33 -177.70(17) . . . . ?
C34 C33 C32 C31 -1.2(3) . . . . ?
C17 C18 C25 C30 -129.1(2) . . . . ?
N4 C18 C25 C30 52.7(2) . . . . ?
C17 C18 C25 C26 48.6(3) . . . . ?
N4 C18 C25 C26 -129.63(18) . . . . ?
C26 C25 C30 C29 0.4(3) . . . . ?
C18 C25 C30 C29 178.09(18) . . . . ?
C25 C30 C29 C28 -0.6(3) . . . . ?
C30 C29 C28 C27 0.1(3) . . . . ?
C29 C28 C27 C26 0.6(3) . . . . ?
C28 C27 C26 C25 -0.7(3) . . . . ?
C30 C25 C26 C27 0.2(3) . . . . ?
C18 C25 C26 C27 -177.50(18) . . . . ?
C18 C17 C19 C20 -148.5(2) . . . . ?
N3 C17 C19 C20 31.8(3) . . . . ?
C18 C17 C19 C24 32.7(3) . . . . ?
N3 C17 C19 C24 -146.96(17) . . . . ?
C20 C19 C24 C23 0.4(3) . . . . ?
C17 C19 C24 C23 179.11(18) . . . . ?
C19 C24 C23 C22 -0.5(3) . . . . ?
C24 C23 C22 C21 -0.1(4) . . . . ?
C23 C22 C21 C20 0.9(4) . . . . ?
C22 C21 C20 C19 -1.1(4) . . . . ?
C24 C19 C20 C21 0.4(3) . . . . ?
C17 C19 C20 C21 -178.4(2) . . . . ?

_refine_diff_density_max         0.346
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_HPIB2
_database_code_depnum_ccdc_archive 'CCDC 1945395'
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2019-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H24 B Cl F2 N4 O'
_chemical_formula_sum            'C36 H24 B Cl F2 N4 O'
_chemical_formula_weight         612.85

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'
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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   9.6016(3)
_cell_length_b                   25.7083(6)
_cell_length_c                   12.6994(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.329(3)
_cell_angle_gamma                90
_cell_volume                     3023.21(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3935
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      25.14

_exptl_crystal_description       Needle
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.176
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26415
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.327
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5303
_reflns_number_gt                4347
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0917P)²+2.1893P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5303
_refine_ls_number_parameters     411
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1780
_refine_ls_wR_factor_gt          0.1602
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl1 Cl 0.28317(8) 0.54058(3) -0.04986(6) 0.0558(3) Uani 1 1 d . . . . .
F1 F 0.2438(3) 0.22223(9) 0.2072(3) 0.1306(12) Uani 1 1 d . . . . .
F2 F 0.2166(3) 0.20898(11) 0.0292(3) 0.1561(16) Uani 1 1 d . . . . .
B1 B 0.2483(4) 0.24505(13) 0.1067(4) 0.0728(11) Uani 1 1 d . . . . .
O1 O 0.5015(2) 0.40057(7) 0.32113(15) 0.0566(5) Uani 1 1 d D . . . .
N2 N 0.1436(3) 0.29126(8) 0.0846(2) 0.0541(6) Uani 1 1 d . . . . .
N1 N 0.4003(3) 0.26778(8) 0.12045(19) 0.0502(6) Uani 1 1 d . . . . .
N4 N 0.6552(2) 0.55358(8) 0.37322(17) 0.0430(5) Uani 1 1 d . . . . .
N3 N 0.6340(2) 0.47456(8) 0.43433(17) 0.0453(5) Uani 1 1 d . . . . .
C9 C -0.0008(3) 0.28909(12) 0.0583(3) 0.0676(9) Uani 1 1 d . . . . .
H9 H -0.056056 0.258140 0.040503 0.081 Uiso 1 1 calc R U . . .
C8 C -0.0583(3) 0.33839(12) 0.0608(3) 0.0652(8) Uani 1 1 d . . . . .
H8 H -0.157778 0.347130 0.045385 0.078 Uiso 1 1 calc R U . . .
C7 C 0.0568(3) 0.37230(10) 0.0899(2) 0.0505(7) Uani 1 1 d . . . . .
H7 H 0.051022 0.408854 0.098883 0.061 Uiso 1 1 calc R U . . .
C6 C 0.1838(3) 0.34310(9) 0.1039(2) 0.0432(6) Uani 1 1 d . . . . .
C5 C 0.3293(3) 0.35781(9) 0.12837(19) 0.0420(6) Uani 1 1 d . . . . .
C4 C 0.4362(3) 0.32045(10) 0.1350(2) 0.0466(6) Uani 1 1 d . . . . .
C3 C 0.5858(3) 0.32479(12) 0.1474(3) 0.0594(8) Uani 1 1 d . . . . .
H3 H 0.640280 0.356098 0.158479 0.071 Uiso 1 1 calc R U . . .
C2 C 0.6386(4) 0.27585(13) 0.1406(3) 0.0694(9) Uani 1 1 d . . . . .
H2 H 0.736182 0.266855 0.146034 0.083 Uiso 1 1 calc R U . . .
C1 C 0.5217(3) 0.24157(12) 0.1242(3) 0.0619(8) Uani 1 1 d . . . . .
H1 H 0.527784 0.204930 0.116752 0.074 Uiso 1 1 calc R U . . .
C10 C 0.3680(3) 0.41412(9) 0.1397(2) 0.0412(6) Uani 1 1 d . . . . .
C15 C 0.3147(3) 0.44726(10) 0.0512(2) 0.0429(6) Uani 1 1 d . . . . .
H15 H 0.253707 0.434130 -0.014959 0.051 Uiso 1 1 calc R U . . .
C14 C 0.3515(3) 0.49936(10) 0.0606(2) 0.0419(6) Uani 1 1 d . . . . .
C13 C 0.4406(3) 0.51914(10) 0.1550(2) 0.0442(6) Uani 1 1 d . . . . .
H13 H 0.465129 0.555017 0.158691 0.053 Uiso 1 1 calc R U . . .
C12 C 0.4956(3) 0.48747(9) 0.2454(2) 0.0410(6) Uani 1 1 d . . . . .
C11 C 0.4570(3) 0.43373(10) 0.2374(2) 0.0427(6) Uani 1 1 d . . . . .
C16 C 0.5918(3) 0.50566(9) 0.3487(2) 0.0420(6) Uani 1 1 d . . . . .
C18 C 0.7422(3) 0.55138(10) 0.4797(2) 0.0448(6) Uani 1 1 d . . . . .
C17 C 0.7273(3) 0.50215(10) 0.5169(2) 0.0436(6) Uani 1 1 d . . . . .
C31 C 0.6521(3) 0.59790(9) 0.3027(2) 0.0431(6) Uani 1 1 d . . . . .
C36 C 0.5433(3) 0.63412(11) 0.2892(3) 0.0579(7) Uani 1 1 d . . . . .
H36 H 0.470871 0.630643 0.327281 0.069 Uiso 1 1 calc R U . . .
C35 C 0.5407(4) 0.67562(12) 0.2195(3) 0.0714(9) Uani 1 1 d . . . . .
H35 H 0.465192 0.700524 0.208727 0.086 Uiso 1 1 calc R U . . .
C34 C 0.6471(4) 0.68115(12) 0.1655(3) 0.0695(9) Uani 1 1 d . . . . .
H34 H 0.643885 0.709445 0.116799 0.083 Uiso 1 1 calc R U . . .
C33 C 0.7578(4) 0.64554(12) 0.1824(2) 0.0624(8) Uani 1 1 d . . . . .
H33 H 0.832846 0.649899 0.147109 0.075 Uiso 1 1 calc R U . . .
C32 C 0.7602(3) 0.60349(11) 0.2505(2) 0.0506(7) Uani 1 1 d . . . . .
H32 H 0.835732 0.578588 0.261290 0.061 Uiso 1 1 calc R U . . .
C25 C 0.8332(3) 0.59594(10) 0.5314(2) 0.0503(7) Uani 1 1 d . . . . .
C30 C 0.7730(4) 0.63922(12) 0.5665(3) 0.0653(8) Uani 1 1 d . . . . .
H30 H 0.671342 0.641862 0.554607 0.078 Uiso 1 1 calc R U . . .
C29 C 0.8641(6) 0.67932(13) 0.6201(3) 0.0836(12) Uani 1 1 d . . . . .
H29 H 0.824193 0.709235 0.644985 0.100 Uiso 1 1 calc R U . . .
C28 C 1.0106(5) 0.67523(16) 0.6365(3) 0.0864(13) Uani 1 1 d . . . . .
H28 H 1.071582 0.702463 0.672710 0.104 Uiso 1 1 calc R U . . .
C27 C 1.0694(5) 0.63304(17) 0.6018(3) 0.0874(12) Uani 1 1 d . . . . .
H27 H 1.171122 0.630832 0.613487 0.105 Uiso 1 1 calc R U . . .
C26 C 0.9827(4) 0.59331(14) 0.5495(3) 0.0688(9) Uani 1 1 d . . . . .
H26 H 1.024965 0.563712 0.525522 0.083 Uiso 1 1 calc R U . . .
C19 C 0.7918(3) 0.47772(10) 0.6234(2) 0.0424(6) Uani 1 1 d . . . . .
C24 C 0.8607(3) 0.50650(11) 0.7155(2) 0.0510(7) Uani 1 1 d . . . . .
H24 H 0.867294 0.543245 0.710451 0.061 Uiso 1 1 calc R U . . .
C23 C 0.9195(3) 0.48205(12) 0.8138(2) 0.0548(7) Uani 1 1 d . . . . .
H23 H 0.967041 0.502133 0.875610 0.066 Uiso 1 1 calc R U . . .
C22 C 0.9103(3) 0.42913(11) 0.8235(2) 0.0537(7) Uani 1 1 d . . . . .
H22 H 0.950831 0.412679 0.891711 0.064 Uiso 1 1 calc R U . . .
C21 C 0.8419(4) 0.40002(11) 0.7339(2) 0.0604(8) Uani 1 1 d . . . . .
H21 H 0.835151 0.363342 0.740200 0.072 Uiso 1 1 calc R U . . .
C20 C 0.7831(3) 0.42397(11) 0.6347(2) 0.0555(7) Uani 1 1 d . . . . .
H20 H 0.736133 0.403511 0.573271 0.067 Uiso 1 1 calc R U . . .
H37 H 0.563(3) 0.4157(10) 0.3844(17) 0.054(8) Uiso 1 1 d 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
Cl1 C14 1.742(2) . ?
F1 B1 1.416(5) . ?
F2 B1 1.328(5) . ?
B1 N2 1.533(4) . ?
B1 N1 1.539(4) . ?
O1 C11 1.342(3) . ?
O1 H37 0.947(17) . ?
N2 C9 1.339(4) . ?
N2 C6 1.391(3) . ?
N1 C1 1.337(4) . ?
N1 C4 1.397(3) . ?
N4 C16 1.373(3) . ?
N4 C18 1.390(3) . ?
N4 C31 1.445(3) . ?
N3 C16 1.324(3) . ?
N3 C17 1.381(3) . ?
C9 C8 1.386(4) . ?
C9 H9 0.9500 . ?
C8 C7 1.379(4) . ?
C8 H8 0.9500 . ?
C7 C6 1.403(4) . ?
C7 H7 0.9500 . ?
C6 C5 1.400(4) . ?
C5 C4 1.392(4) . ?
C5 C10 1.492(3) . ?
C4 C3 1.408(4) . ?
C3 C2 1.368(4) . ?
C3 H3 0.9500 . ?
C2 C1 1.398(5) . ?
C2 H2 0.9500 . ?
C1 H1 0.9500 . ?
C10 C15 1.395(3) . ?
C10 C11 1.401(3) . ?
C15 C14 1.382(3) . ?
C15 H15 0.9500 . ?
C14 C13 1.373(4) . ?
C13 C12 1.393(4) . ?
C13 H13 0.9500 . ?
C12 C11 1.427(3) . ?
C12 C16 1.467(4) . ?
C18 C17 1.372(4) . ?
C18 C25 1.484(3) . ?
C17 C19 1.472(4) . ?
C31 C36 1.376(4) . ?
C31 C32 1.378(4) . ?
C36 C35 1.382(4) . ?
C36 H36 0.9500 . ?
C35 C34 1.380(5) . ?
C35 H35 0.9500 . ?
C34 C33 1.376(5) . ?
C34 H34 0.9500 . ?
C33 C32 1.381(4) . ?
C33 H33 0.9500 . ?
C32 H32 0.9500 . ?
C25 C30 1.381(4) . ?
C25 C26 1.394(4) . ?
C30 C29 1.406(5) . ?
C30 H30 0.9500 . ?
C29 C28 1.370(6) . ?
C29 H29 0.9500 . ?
C28 C27 1.349(6) . ?
C28 H28 0.9500 . ?
C27 C26 1.373(5) . ?
C27 H27 0.9500 . ?
C26 H26 0.9500 . ?
C19 C20 1.394(4) . ?
C19 C24 1.394(4) . ?
C24 C23 1.378(4) . ?
C24 H24 0.9500 . ?
C23 C22 1.371(4) . ?
C23 H23 0.9500 . ?
C22 C21 1.375(4) . ?
C22 H22 0.9500 . ?
C21 C20 1.382(4) . ?
C21 H21 0.9500 . ?
C20 H20 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
F2 B1 F1 108.9(3) . . ?
F2 B1 N2 113.2(4) . . ?
F1 B1 N2 108.2(3) . . ?
F2 B1 N1 111.9(3) . . ?
F1 B1 N1 108.0(3) . . ?
N2 B1 N1 106.4(2) . . ?
C11 O1 H37 114.0(17) . . ?
C9 N2 C6 107.7(2) . . ?
C9 N2 B1 126.8(3) . . ?
C6 N2 B1 124.9(2) . . ?
C1 N1 C4 107.6(2) . . ?
C1 N1 B1 127.2(2) . . ?
C4 N1 B1 125.2(2) . . ?
C16 N4 C18 107.5(2) . . ?
C16 N4 C31 129.2(2) . . ?
C18 N4 C31 122.9(2) . . ?
C16 N3 C17 108.1(2) . . ?
N2 C9 C8 110.4(3) . . ?
N2 C9 H9 124.8 . . ?
C8 C9 H9 124.8 . . ?
C7 C8 C9 106.8(3) . . ?
C7 C8 H8 126.6 . . ?
C9 C8 H8 126.6 . . ?
C8 C7 C6 107.7(3) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 . . ?
N2 C6 C5 120.8(2) . . ?
N2 C6 C7 107.4(2) . . ?
C5 C6 C7 131.8(2) . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 C10 120.2(2) . . ?
C6 C5 C10 119.5(2) . . ?
C5 C4 N1 120.6(2) . . ?
C5 C4 C3 131.8(2) . . ?
N1 C4 C3 107.5(2) . . ?
C2 C3 C4 107.7(3) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
C3 C2 C1 107.0(3) . . ?
C3 C2 H2 126.5 . . ?
C1 C2 H2 126.5 . . ?
N1 C1 C2 110.2(3) . . ?
N1 C1 H1 124.9 . . ?
C2 C1 H1 124.9 . . ?
C15 C10 C11 120.1(2) . . ?
C15 C10 C5 119.1(2) . . ?
C11 C10 C5 120.8(2) . . ?
C14 C15 C10 119.4(2) . . ?
C14 C15 H15 120.3 . . ?
C10 C15 H15 120.3 . . ?
C13 C14 C15 121.3(2) . . ?
C13 C14 Cl1 119.52(19) . . ?
C15 C14 Cl1 119.1(2) . . ?
C14 C13 C12 121.1(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C12 C11 118.2(2) . . ?
C13 C12 C16 124.2(2) . . ?
C11 C12 C16 117.5(2) . . ?
O1 C11 C10 117.7(2) . . ?
O1 C11 C12 122.5(2) . . ?
C10 C11 C12 119.8(2) . . ?
N3 C16 N4 109.5(2) . . ?
N3 C16 C12 121.7(2) . . ?
N4 C16 C12 128.7(2) . . ?
C17 C18 N4 106.4(2) . . ?
C17 C18 C25 131.5(2) . . ?
N4 C18 C25 122.1(2) . . ?
C18 C17 N3 108.6(2) . . ?
C18 C17 C19 130.8(2) . . ?
N3 C17 C19 120.6(2) . . ?
C36 C31 C32 120.9(3) . . ?
C36 C31 N4 120.1(2) . . ?
C32 C31 N4 119.1(2) . . ?
C31 C36 C35 119.1(3) . . ?
C31 C36 H36 120.5 . . ?
C35 C36 H36 120.5 . . ?
C34 C35 C36 120.5(3) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C33 C34 C35 119.8(3) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C34 C33 C32 120.1(3) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C31 C32 C33 119.6(3) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C30 C25 C26 119.1(3) . . ?
C30 C25 C18 121.1(3) . . ?
C26 C25 C18 119.7(3) . . ?
C25 C30 C29 119.1(4) . . ?
C25 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?
C28 C29 C30 120.0(4) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C27 C28 C29 120.9(3) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C28 C27 C26 120.2(4) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C26 C25 120.7(4) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C20 C19 C24 117.9(2) . . ?
C20 C19 C17 119.7(2) . . ?
C24 C19 C17 122.4(2) . . ?
C23 C24 C19 120.5(3) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C22 C23 C24 120.9(3) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C23 C22 C21 119.6(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?

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
F2 B1 N2 C9 50.4(5) . . . . ?
F1 B1 N2 C9 -70.4(5) . . . . ?
N1 B1 N2 C9 173.8(3) . . . . ?
F2 B1 N2 C6 -139.5(3) . . . . ?
F1 B1 N2 C6 99.8(3) . . . . ?
N1 B1 N2 C6 -16.0(5) . . . . ?
F2 B1 N1 C1 -44.7(5) . . . . ?
F1 B1 N1 C1 75.2(4) . . . . ?
N2 B1 N1 C1 -168.9(3) . . . . ?
F2 B1 N1 C4 137.6(3) . . . . ?
F1 B1 N1 C4 -102.6(3) . . . . ?
N2 B1 N1 C4 13.3(5) . . . . ?
C6 N2 C9 C8 -0.6(4) . . . . ?
B1 N2 C9 C8 170.9(3) . . . . ?
N2 C9 C8 C7 0.1(4) . . . . ?
C9 C8 C7 C6 0.5(4) . . . . ?
C9 N2 C6 C5 -177.0(3) . . . . ?
B1 N2 C6 C5 11.2(4) . . . . ?
C9 N2 C6 C7 1.0(3) . . . . ?
B1 N2 C6 C7 -170.8(3) . . . . ?
C8 C7 C6 N2 -0.9(3) . . . . ?
C8 C7 C6 C5 176.7(3) . . . . ?
N2 C6 C5 C4 -0.8(4) . . . . ?
C7 C6 C5 C4 -178.2(3) . . . . ?
N2 C6 C5 C10 175.0(2) . . . . ?
C7 C6 C5 C10 -2.4(4) . . . . ?
C6 C5 C4 N1 -1.8(4) . . . . ?
C10 C5 C4 N1 -177.6(2) . . . . ?
C6 C5 C4 C3 173.0(3) . . . . ?
C10 C5 C4 C3 -2.8(4) . . . . ?
C1 N1 C4 C5 176.1(3) . . . . ?
B1 N1 C4 C5 -5.7(4) . . . . ?
C1 N1 C4 C3 0.2(3) . . . . ?
B1 N1 C4 C3 178.3(3) . . . . ?
C5 C4 C3 C2 -175.4(3) . . . . ?
N1 C4 C3 C2 -0.1(3) . . . . ?
C4 C3 C2 C1 -0.1(4) . . . . ?
C4 N1 C1 C2 -0.2(4) . . . . ?
B1 N1 C1 C2 -178.3(3) . . . . ?
C3 C2 C1 N1 0.2(4) . . . . ?
C4 C5 C10 C15 116.2(3) . . . . ?
C6 C5 C10 C15 -59.6(3) . . . . ?
C4 C5 C10 C11 -63.6(3) . . . . ?
C6 C5 C10 C11 120.5(3) . . . . ?
C11 C10 C15 C14 0.6(4) . . . . ?
C5 C10 C15 C14 -179.2(2) . . . . ?
C10 C15 C14 C13 0.6(4) . . . . ?
C10 C15 C14 Cl1 -179.4(2) . . . . ?
C15 C14 C13 C12 -0.9(4) . . . . ?
Cl1 C14 C13 C12 179.1(2) . . . . ?
C14 C13 C12 C11 0.0(4) . . . . ?
C14 C13 C12 C16 179.7(2) . . . . ?
C15 C10 C11 O1 177.9(2) . . . . ?
C5 C10 C11 O1 -2.3(4) . . . . ?
C15 C10 C11 C12 -1.4(4) . . . . ?
C5 C10 C11 C12 178.4(2) . . . . ?
C13 C12 C11 O1 -178.1(2) . . . . ?
C16 C12 C11 O1 2.2(4) . . . . ?
C13 C12 C11 C10 1.1(4) . . . . ?
C16 C12 C11 C10 -178.6(2) . . . . ?
C17 N3 C16 N4 -0.2(3) . . . . ?
C17 N3 C16 C12 177.8(2) . . . . ?
C18 N4 C16 N3 0.6(3) . . . . ?
C31 N4 C16 N3 173.5(2) . . . . ?
C18 N4 C16 C12 -177.3(3) . . . . ?
C31 N4 C16 C12 -4.3(4) . . . . ?
C13 C12 C16 N3 175.9(2) . . . . ?
C11 C12 C16 N3 -4.5(4) . . . . ?
C13 C12 C16 N4 -6.5(4) . . . . ?
C11 C12 C16 N4 173.1(2) . . . . ?
C16 N4 C18 C17 -0.7(3) . . . . ?
C31 N4 C18 C17 -174.2(2) . . . . ?
C16 N4 C18 C25 176.9(2) . . . . ?
C31 N4 C18 C25 3.5(4) . . . . ?
N4 C18 C17 N3 0.6(3) . . . . ?
C25 C18 C17 N3 -176.8(3) . . . . ?
N4 C18 C17 C19 -179.2(3) . . . . ?
C25 C18 C17 C19 3.4(5) . . . . ?
C16 N3 C17 C18 -0.2(3) . . . . ?
C16 N3 C17 C19 179.6(2) . . . . ?
C16 N4 C31 C36 88.7(3) . . . . ?
C18 N4 C31 C36 -99.3(3) . . . . ?
C16 N4 C31 C32 -91.9(3) . . . . ?
C18 N4 C31 C32 80.0(3) . . . . ?
C32 C31 C36 C35 2.1(4) . . . . ?
N4 C31 C36 C35 -178.6(3) . . . . ?
C31 C36 C35 C34 -1.0(5) . . . . ?
C36 C35 C34 C33 -1.0(5) . . . . ?
C35 C34 C33 C32 2.0(5) . . . . ?
C36 C31 C32 C33 -1.1(4) . . . . ?
N4 C31 C32 C33 179.6(2) . . . . ?
C34 C33 C32 C31 -1.0(5) . . . . ?
C17 C18 C25 C30 -108.1(4) . . . . ?
N4 C18 C25 C30 74.9(4) . . . . ?
C17 C18 C25 C26 69.0(4) . . . . ?
N4 C18 C25 C26 -108.0(3) . . . . ?
C26 C25 C30 C29 -0.3(5) . . . . ?
C18 C25 C30 C29 176.7(3) . . . . ?
C25 C30 C29 C28 0.3(5) . . . . ?
C30 C29 C28 C27 0.0(6) . . . . ?
C29 C28 C27 C26 -0.2(6) . . . . ?
C28 C27 C26 C25 0.1(6) . . . . ?
C30 C25 C26 C27 0.1(5) . . . . ?
C18 C25 C26 C27 -177.0(3) . . . . ?
C18 C17 C19 C20 -167.0(3) . . . . ?
N3 C17 C19 C20 13.2(4) . . . . ?
C18 C17 C19 C24 13.8(4) . . . . ?
N3 C17 C19 C24 -166.0(3) . . . . ?
C20 C19 C24 C23 0.7(4) . . . . ?
C17 C19 C24 C23 179.9(3) . . . . ?
C19 C24 C23 C22 -0.6(4) . . . . ?
C24 C23 C22 C21 0.2(5) . . . . ?
C23 C22 C21 C20 0.1(5) . . . . ?
C22 C21 C20 C19 0.0(5) . . . . ?
C24 C19 C20 C21 -0.4(4) . . . . ?
C17 C19 C20 C21 -179.6(3) . . . . ?

_refine_diff_density_max         0.735
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.117

####################################################################### 
# 
# 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_HPIB4
_database_code_depnum_ccdc_archive 'CCDC 1945397'
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2019-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H23 B Cl2 F2 N4 O'
_chemical_formula_sum            'C36 H23 B Cl2 F2 N4 O'
_chemical_formula_weight         647.29

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'
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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5668(7)
_cell_length_b                   13.2433(9)
_cell_length_c                   13.9708(9)
_cell_angle_alpha                104.534(2)
_cell_angle_beta                 103.397(2)
_cell_angle_gamma                104.401(2)
_cell_volume                     1575.80(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4235
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      25.15

_exptl_crystal_description       Needle
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.254
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38778
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.066
_diffrn_reflns_theta_max         27.554
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7265
_reflns_number_gt                5029
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+0.8721P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7265
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1260
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Cl1 Cl 0.80139(7) 1.03822(5) -0.08890(4) 0.05904(17) Uani 1 1 d . . . . .
Cl2 Cl 0.61541(10) 0.64958(6) -0.49091(5) 0.0809(2) Uani 1 1 d . . . . .
F1 F 0.92675(18) 1.21758(13) 0.59666(10) 0.0719(4) Uani 1 1 d . . . . .
F2 F 0.99514(17) 1.31072(10) 0.49092(12) 0.0712(4) Uani 1 1 d . . . . .
O1 O 0.80982(18) 0.81999(11) 0.22701(10) 0.0488(4) Uani 1 1 d . . . . .
H37 H 0.795083 0.753685 0.202863 0.073 Uiso 1 1 calc R U . . .
N2 N 0.7718(2) 1.15184(13) 0.41660(12) 0.0432(4) Uani 1 1 d . . . . .
N1 N 1.02481(19) 1.13208(13) 0.46612(12) 0.0421(4) Uani 1 1 d . . . . .
N3 N 0.77355(19) 0.63985(12) 0.09676(12) 0.0404(4) Uani 1 1 d . . . . .
C8 C 0.5286(3) 1.1144(2) 0.3267(2) 0.0603(6) Uani 1 1 d . . . . .
H8 H 0.428426 1.113881 0.310816 0.072 Uiso 1 1 calc R U . . .
C7 C 0.5925(3) 1.05952(18) 0.26067(18) 0.0503(5) Uani 1 1 d . . . . .
H7 H 0.543330 1.015139 0.191630 0.060 Uiso 1 1 calc R U . . .
C6 C 0.7449(2) 1.08276(15) 0.31640(15) 0.0389(4) Uani 1 1 d . . . . .
C5 C 0.8588(2) 1.04456(14) 0.28935(14) 0.0361(4) Uani 1 1 d . . . . .
C10 C 0.8298(2) 0.97824(15) 0.17893(14) 0.0368(4) Uani 1 1 d . . . . .
C11 C 0.8064(2) 0.86487(15) 0.15095(14) 0.0364(4) Uani 1 1 d . . . . .
C12 C 0.7812(2) 0.80313(15) 0.04586(14) 0.0356(4) Uani 1 1 d . . . . .
C16 C 0.7625(2) 0.68520(15) 0.02221(14) 0.0369(4) Uani 1 1 d . . . . .
N4 N 0.73635(18) 0.60699(12) -0.07136(11) 0.0368(4) Uani 1 1 d . . . . .
C18 C 0.7304(2) 0.50779(15) -0.05228(15) 0.0378(4) Uani 1 1 d . . . . .
C25 C 0.7086(2) 0.40466(15) -0.13424(14) 0.0387(4) Uani 1 1 d . . . . .
C30 C 0.5688(3) 0.3411(2) -0.2037(2) 0.0789(9) Uani 1 1 d . . . . .
H30 H 0.485632 0.365477 -0.203784 0.095 Uiso 1 1 calc R U . . .
C29 C 0.5509(3) 0.2406(2) -0.2739(3) 0.0976(12) Uani 1 1 d . . . . .
H29 H 0.454780 0.196916 -0.319403 0.117 Uiso 1 1 calc R U . . .
C28 C 0.6711(3) 0.2050(2) -0.27722(19) 0.0659(7) Uani 1 1 d . . . . .
H28 H 0.657949 0.138231 -0.326037 0.079 Uiso 1 1 calc R U . . .
C4 C 0.9961(2) 1.06696(15) 0.36382(14) 0.0394(4) Uani 1 1 d . . . . .
C1 C 1.1542(3) 1.12851(19) 0.52286(16) 0.0526(5) Uani 1 1 d . . . . .
H1 H 1.198698 1.165019 0.594088 0.063 Uiso 1 1 calc R U . . .
C2 C 1.2149(3) 1.06217(19) 0.46081(17) 0.0541(5) Uani 1 1 d . . . . .
H2 H 1.304091 1.046477 0.483011 0.065 Uiso 1 1 calc R U . . .
C3 C 1.1178(2) 1.02505(17) 0.36141(16) 0.0470(5) Uani 1 1 d . . . . .
H3 H 1.129570 0.980372 0.302875 0.056 Uiso 1 1 calc R U . . .
C15 C 0.8276(2) 1.03054(16) 0.10454(15) 0.0409(4) Uani 1 1 d . . . . .
H15 H 0.843020 1.105931 0.123211 0.049 Uiso 1 1 calc R U . . .
C14 C 0.8024(2) 0.96995(16) 0.00255(14) 0.0407(4) Uani 1 1 d . . . . .
C13 C 0.7791(2) 0.85835(16) -0.02732(14) 0.0407(4) Uani 1 1 d . . . . .
H13 H 0.761710 0.819367 -0.096678 0.049 Uiso 1 1 calc R U . . .
C17 C 0.7535(2) 0.53007(15) 0.05222(15) 0.0387(4) Uani 1 1 d . . . . .
C31 C 0.7100(2) 0.61794(15) -0.17352(14) 0.0373(4) Uani 1 1 d . . . . .
C32 C 0.8269(3) 0.6362(2) -0.21518(17) 0.0531(5) Uani 1 1 d . . . . .
H32 H 0.923948 0.641296 -0.177889 0.064 Uiso 1 1 calc R U . . .
C33 C 0.7986(3) 0.6469(2) -0.31346(19) 0.0608(6) Uani 1 1 d . . . . .
H33 H 0.876732 0.659769 -0.342544 0.073 Uiso 1 1 calc R U . . .
C34 C 0.6547(3) 0.63824(17) -0.36726(16) 0.0498(5) Uani 1 1 d . . . . .
C35 C 0.5377(3) 0.61922(19) -0.32590(17) 0.0531(5) Uani 1 1 d . . . . .
H35 H 0.440497 0.613918 -0.363172 0.064 Uiso 1 1 calc R U . . .
C36 C 0.5659(2) 0.60809(18) -0.22850(16) 0.0467(5) Uani 1 1 d . . . . .
H36 H 0.487247 0.593909 -0.200069 0.056 Uiso 1 1 calc R U . . .
C27 C 0.8107(3) 0.2669(2) -0.2093(2) 0.0631(7) Uani 1 1 d . . . . .
H27 H 0.893517 0.242437 -0.210721 0.076 Uiso 1 1 calc R U . . .
C26 C 0.8296(3) 0.36671(18) -0.13763(18) 0.0551(6) Uani 1 1 d . . . . .
H26 H 0.925644 0.408876 -0.091001 0.066 Uiso 1 1 calc R U . . .
C19 C 0.7627(2) 0.45892(15) 0.11723(15) 0.0405(4) Uani 1 1 d . . . . .
C20 C 0.8408(3) 0.50591(18) 0.22319(17) 0.0495(5) Uani 1 1 d . . . . .
H20 H 0.887384 0.581959 0.251761 0.059 Uiso 1 1 calc R U . . .
C21 C 0.8502(3) 0.4415(2) 0.28669(19) 0.0574(6) Uani 1 1 d . . . . .
H21 H 0.903475 0.474186 0.357380 0.069 Uiso 1 1 calc R U . . .
C22 C 0.7812(3) 0.3291(2) 0.2458(2) 0.0606(6) Uani 1 1 d . . . . .
H22 H 0.787200 0.285587 0.288466 0.073 Uiso 1 1 calc R U . . .
C23 C 0.7031(3) 0.28163(19) 0.1413(2) 0.0600(6) Uani 1 1 d . . . . .
H23 H 0.656161 0.205573 0.113581 0.072 Uiso 1 1 calc R U . . .
C24 C 0.6933(3) 0.34502(17) 0.07665(18) 0.0512(5) Uani 1 1 d . . . . .
H24 H 0.640257 0.311523 0.005992 0.061 Uiso 1 1 calc R U . . .
C9 C 0.6422(3) 1.17039(19) 0.42142(19) 0.0564(6) Uani 1 1 d . . . . .
H9 H 0.629859 1.214607 0.479999 0.068 Uiso 1 1 calc R U . . .
B1 B 0.9312(3) 1.2080(2) 0.49843(18) 0.0477(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
Cl1 C14 1.7402(19) . ?
Cl2 C34 1.734(2) . ?
F1 B1 1.358(3) . ?
F2 B1 1.387(3) . ?
O1 C11 1.339(2) . ?
O1 H37 0.8200 . ?
N2 C9 1.336(3) . ?
N2 C6 1.391(2) . ?
N2 B1 1.544(3) . ?
N1 C1 1.325(3) . ?
N1 C4 1.394(2) . ?
N1 B1 1.557(3) . ?
N3 C16 1.323(2) . ?
N3 C17 1.375(2) . ?
C8 C7 1.378(3) . ?
C8 C9 1.386(3) . ?
C8 H8 0.9300 . ?
C7 C6 1.399(3) . ?
C7 H7 0.9300 . ?
C6 C5 1.398(3) . ?
C5 C4 1.384(3) . ?
C5 C10 1.493(2) . ?
C10 C15 1.385(3) . ?
C10 C11 1.398(3) . ?
C11 C12 1.420(2) . ?
C12 C13 1.398(3) . ?
C12 C16 1.468(3) . ?
C16 N4 1.373(2) . ?
N4 C18 1.395(2) . ?
N4 C31 1.441(2) . ?
C18 C17 1.367(3) . ?
C18 C25 1.477(3) . ?
C25 C30 1.366(3) . ?
C25 C26 1.378(3) . ?
C30 C29 1.384(3) . ?
C30 H30 0.9300 . ?
C29 C28 1.353(4) . ?
C29 H29 0.9300 . ?
C28 C27 1.354(3) . ?
C28 H28 0.9300 . ?
C4 C3 1.412(3) . ?
C1 C2 1.402(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(3) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C15 C14 1.379(3) . ?
C15 H15 0.9300 . ?
C14 C13 1.375(3) . ?
C13 H13 0.9300 . ?
C17 C19 1.468(3) . ?
C31 C36 1.370(3) . ?
C31 C32 1.373(3) . ?
C32 C33 1.387(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.368(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.373(3) . ?
C35 C36 1.377(3) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C27 C26 1.384(3) . ?
C27 H27 0.9300 . ?
C26 H26 0.9300 . ?
C19 C20 1.389(3) . ?
C19 C24 1.391(3) . ?
C20 C21 1.380(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.372(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.382(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C9 H9 0.9300 . ?

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
C11 O1 H37 109.5 . . ?
C9 N2 C6 107.61(18) . . ?
C9 N2 B1 128.09(18) . . ?
C6 N2 B1 123.71(17) . . ?
C1 N1 C4 107.49(17) . . ?
C1 N1 B1 128.28(17) . . ?
C4 N1 B1 123.52(17) . . ?
C16 N3 C17 108.01(15) . . ?
C7 C8 C9 106.8(2) . . ?
C7 C8 H8 126.6 . . ?
C9 C8 H8 126.6 . . ?
C8 C7 C6 107.5(2) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 . . ?
N2 C6 C5 120.71(18) . . ?
N2 C6 C7 107.62(17) . . ?
C5 C6 C7 131.56(18) . . ?
C4 C5 C6 120.62(17) . . ?
C4 C5 C10 120.29(17) . . ?
C6 C5 C10 119.09(17) . . ?
C15 C10 C11 120.32(16) . . ?
C15 C10 C5 119.20(16) . . ?
C11 C10 C5 120.49(16) . . ?
O1 C11 C10 116.95(16) . . ?
O1 C11 C12 123.20(16) . . ?
C10 C11 C12 119.85(16) . . ?
C13 C12 C11 118.37(16) . . ?
C13 C12 C16 124.44(16) . . ?
C11 C12 C16 117.17(16) . . ?
N3 C16 N4 109.61(16) . . ?
N3 C16 C12 120.96(16) . . ?
N4 C16 C12 129.41(17) . . ?
C16 N4 C18 107.21(15) . . ?
C16 N4 C31 128.82(16) . . ?
C18 N4 C31 123.88(15) . . ?
C17 C18 N4 106.21(16) . . ?
C17 C18 C25 130.66(18) . . ?
N4 C18 C25 123.09(17) . . ?
C30 C25 C26 118.26(19) . . ?
C30 C25 C18 121.82(19) . . ?
C26 C25 C18 119.79(18) . . ?
C25 C30 C29 120.1(2) . . ?
C25 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C28 C29 C30 121.0(2) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 H29 119.5 . . ?
C29 C28 C27 119.8(2) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C5 C4 N1 120.17(17) . . ?
C5 C4 C3 131.79(17) . . ?
N1 C4 C3 107.60(17) . . ?
N1 C1 C2 110.71(19) . . ?
N1 C1 H1 124.6 . . ?
C2 C1 H1 124.6 . . ?
C3 C2 C1 106.7(2) . . ?
C3 C2 H2 126.6 . . ?
C1 C2 H2 126.6 . . ?
C2 C3 C4 107.46(18) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
C14 C15 C10 119.50(17) . . ?
C14 C15 H15 120.3 . . ?
C10 C15 H15 120.3 . . ?
C13 C14 C15 121.51(17) . . ?
C13 C14 Cl1 120.11(15) . . ?
C15 C14 Cl1 118.38(15) . . ?
C14 C13 C12 120.45(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C18 C17 N3 108.95(16) . . ?
C18 C17 C19 130.92(17) . . ?
N3 C17 C19 120.11(16) . . ?
C36 C31 C32 120.92(19) . . ?
C36 C31 N4 118.67(17) . . ?
C32 C31 N4 120.40(18) . . ?
C31 C32 C33 119.3(2) . . ?
C31 C32 H32 120.4 . . ?
C33 C32 H32 120.4 . . ?
C34 C33 C32 119.4(2) . . ?
C34 C33 H33 120.3 . . ?
C32 C33 H33 120.3 . . ?
C33 C34 C35 121.3(2) . . ?
C33 C34 Cl2 120.44(18) . . ?
C35 C34 Cl2 118.23(18) . . ?
C34 C35 C36 119.2(2) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
C31 C36 C35 119.9(2) . . ?
C31 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C28 C27 C26 119.7(2) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C25 C26 C27 121.1(2) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C20 C19 C24 118.29(19) . . ?
C20 C19 C17 119.57(17) . . ?
C24 C19 C17 122.14(19) . . ?
C21 C20 C19 121.0(2) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 119.4(2) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 121.1(2) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C23 C24 C19 120.0(2) . . ?
C23 C24 H24 120.0 . . ?
C19 C24 H24 120.0 . . ?
N2 C9 C8 110.4(2) . . ?
N2 C9 H9 124.8 . . ?
C8 C9 H9 124.8 . . ?
F1 B1 F2 110.61(18) . . ?
F1 B1 N2 112.22(19) . . ?
F2 B1 N2 109.06(19) . . ?
F1 B1 N1 110.86(19) . . ?
F2 B1 N1 109.15(19) . . ?
N2 B1 N1 104.75(16) . . ?

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
C9 C8 C7 C6 0.2(3) . . . . ?
C9 N2 C6 C5 -176.95(18) . . . . ?
B1 N2 C6 C5 11.2(3) . . . . ?
C9 N2 C6 C7 -0.4(2) . . . . ?
B1 N2 C6 C7 -172.21(19) . . . . ?
C8 C7 C6 N2 0.1(2) . . . . ?
C8 C7 C6 C5 176.2(2) . . . . ?
N2 C6 C5 C4 5.5(3) . . . . ?
C7 C6 C5 C4 -170.1(2) . . . . ?
N2 C6 C5 C10 -175.02(16) . . . . ?
C7 C6 C5 C10 9.4(3) . . . . ?
C4 C5 C10 C15 -107.7(2) . . . . ?
C6 C5 C10 C15 72.8(2) . . . . ?
C4 C5 C10 C11 71.8(2) . . . . ?
C6 C5 C10 C11 -107.7(2) . . . . ?
C15 C10 C11 O1 -179.86(18) . . . . ?
C5 C10 C11 O1 0.7(3) . . . . ?
C15 C10 C11 C12 0.4(3) . . . . ?
C5 C10 C11 C12 -179.07(17) . . . . ?
O1 C11 C12 C13 179.60(18) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
O1 C11 C12 C16 -1.7(3) . . . . ?
C10 C11 C12 C16 178.06(18) . . . . ?
C17 N3 C16 N4 -0.5(2) . . . . ?
C17 N3 C16 C12 -179.05(17) . . . . ?
C13 C12 C16 N3 176.53(19) . . . . ?
C11 C12 C16 N3 -2.1(3) . . . . ?
C13 C12 C16 N4 -1.7(3) . . . . ?
C11 C12 C16 N4 179.64(18) . . . . ?
N3 C16 N4 C18 0.4(2) . . . . ?
C12 C16 N4 C18 178.79(19) . . . . ?
N3 C16 N4 C31 176.89(17) . . . . ?
C12 C16 N4 C31 -4.7(3) . . . . ?
C16 N4 C18 C17 -0.1(2) . . . . ?
C31 N4 C18 C17 -176.86(17) . . . . ?
C16 N4 C18 C25 -178.07(17) . . . . ?
C31 N4 C18 C25 5.2(3) . . . . ?
C17 C18 C25 C30 104.0(3) . . . . ?
N4 C18 C25 C30 -78.6(3) . . . . ?
C17 C18 C25 C26 -71.7(3) . . . . ?
N4 C18 C25 C26 105.7(2) . . . . ?
C26 C25 C30 C29 1.1(5) . . . . ?
C18 C25 C30 C29 -174.7(3) . . . . ?
C25 C30 C29 C28 -2.0(6) . . . . ?
C30 C29 C28 C27 1.8(5) . . . . ?
C6 C5 C4 N1 -2.7(3) . . . . ?
C10 C5 C4 N1 177.80(17) . . . . ?
C6 C5 C4 C3 168.6(2) . . . . ?
C10 C5 C4 C3 -10.9(3) . . . . ?
C1 N1 C4 C5 172.17(18) . . . . ?
B1 N1 C4 C5 -16.8(3) . . . . ?
C1 N1 C4 C3 -1.1(2) . . . . ?
B1 N1 C4 C3 170.00(18) . . . . ?
C4 N1 C1 C2 0.2(3) . . . . ?
B1 N1 C1 C2 -170.3(2) . . . . ?
N1 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C5 C4 C3 C2 -170.6(2) . . . . ?
N1 C4 C3 C2 1.5(2) . . . . ?
C11 C10 C15 C14 -0.1(3) . . . . ?
C5 C10 C15 C14 179.37(18) . . . . ?
C10 C15 C14 C13 0.1(3) . . . . ?
C10 C15 C14 Cl1 -179.64(15) . . . . ?
C15 C14 C13 C12 -0.4(3) . . . . ?
Cl1 C14 C13 C12 179.34(15) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C16 C12 C13 C14 -177.95(19) . . . . ?
N4 C18 C17 N3 -0.2(2) . . . . ?
C25 C18 C17 N3 177.58(19) . . . . ?
N4 C18 C17 C19 -178.4(2) . . . . ?
C25 C18 C17 C19 -0.7(4) . . . . ?
C16 N3 C17 C18 0.4(2) . . . . ?
C16 N3 C17 C19 178.89(17) . . . . ?
C16 N4 C31 C36 -83.3(2) . . . . ?
C18 N4 C31 C36 92.7(2) . . . . ?
C16 N4 C31 C32 97.7(2) . . . . ?
C18 N4 C31 C32 -86.3(2) . . . . ?
C36 C31 C32 C33 1.3(3) . . . . ?
N4 C31 C32 C33 -179.7(2) . . . . ?
C31 C32 C33 C34 -0.5(4) . . . . ?
C32 C33 C34 C35 0.0(4) . . . . ?
C32 C33 C34 Cl2 -179.23(19) . . . . ?
C33 C34 C35 C36 -0.3(3) . . . . ?
Cl2 C34 C35 C36 178.92(17) . . . . ?
C32 C31 C36 C35 -1.6(3) . . . . ?
N4 C31 C36 C35 179.39(19) . . . . ?
C34 C35 C36 C31 1.1(3) . . . . ?
C29 C28 C27 C26 -0.7(5) . . . . ?
C30 C25 C26 C27 -0.1(4) . . . . ?
C18 C25 C26 C27 175.8(2) . . . . ?
C28 C27 C26 C25 -0.1(4) . . . . ?
C18 C17 C19 C20 156.0(2) . . . . ?
N3 C17 C19 C20 -22.1(3) . . . . ?
C18 C17 C19 C24 -25.1(3) . . . . ?
N3 C17 C19 C24 156.80(19) . . . . ?
C24 C19 C20 C21 0.4(3) . . . . ?
C17 C19 C20 C21 179.3(2) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
C21 C22 C23 C24 0.2(4) . . . . ?
C22 C23 C24 C19 -0.2(3) . . . . ?
C20 C19 C24 C23 0.0(3) . . . . ?
C17 C19 C24 C23 -179.0(2) . . . . ?
C6 N2 C9 C8 0.5(3) . . . . ?
B1 N2 C9 C8 171.8(2) . . . . ?
C7 C8 C9 N2 -0.4(3) . . . . ?
C9 N2 B1 F1 44.1(3) . . . . ?
C6 N2 B1 F1 -145.84(19) . . . . ?
C9 N2 B1 F2 -78.8(3) . . . . ?
C6 N2 B1 F2 91.2(2) . . . . ?
C9 N2 B1 N1 164.45(19) . . . . ?
C6 N2 B1 N1 -25.5(3) . . . . ?
C1 N1 B1 F1 -41.3(3) . . . . ?
C4 N1 B1 F1 149.59(19) . . . . ?
C1 N1 B1 F2 80.8(3) . . . . ?
C4 N1 B1 F2 -88.3(2) . . . . ?
C1 N1 B1 N2 -162.5(2) . . . . ?
C4 N1 B1 N2 28.3(3) . . . . ?

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
C1 H1 O1 0.93 2.48 3.305(3) 148.1 2_776
O1 H37 N3 0.82 1.76 2.498(2) 149.0 .
C1 H1 O1 0.93 2.48 3.305(3) 148.1 2_776

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.046

