# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_19gtu097_bc_eo_77_dcm_0ma
_database_code_depnum_ccdc_archive 'CCDC 2011924'
loop_
_audit_author_name
_audit_author_address
'Yunus Zorlu' 'Gebze Technical University'
_audit_update_record             
;
2020-06-24 deposited with the CCDC.	2020-12-07 downloaded from the CCDC.
;
_audit_creation_date             2020-06-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 B F2 N3'
_chemical_formula_sum            'C18 H18 B F2 N3'
_chemical_formula_weight         325.16
_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/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                   24.878(4)
_cell_length_b                   6.8029(13)
_cell_length_c                   20.937(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.088(9)
_cell_angle_gamma                90
_cell_volume                     3234.9(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2723
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.78
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_av_unetI/netI     0.0810
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25315
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         0.897
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3257
_reflns_number_total             5674
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0079(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         5674
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0767
_refine_ls_restrained_S_all      1.083
_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)+(0.0772P)²+3.0671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1958
_refine_ls_wR_factor_ref         0.2158
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C26(H26),
 C33(H33), C34(H34), C35(H35), C36(H36)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,
 H31B,H31C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.97752(12) 0.7182(4) 0.54782(15) 0.0749(9) Uani 1 1 d . . . . .
F2 F 0.89702(14) 0.8917(4) 0.48004(12) 0.0722(9) Uani 1 1 d . . . . .
N1 N 0.92883(14) 0.9064(5) 0.60483(16) 0.0431(8) Uani 1 1 d . . . . .
N2 N 0.88352(15) 0.6057(5) 0.53820(16) 0.0435(8) Uani 1 1 d . . . . .
N3 N 0.7933(2) 0.5752(7) 0.7887(2) 0.0680(12) Uani 1 1 d . . . . .
C1 C 0.95850(19) 1.0775(7) 0.6249(2) 0.0489(11) Uani 1 1 d . . . . .
C2 C 0.95604(19) 1.1402(7) 0.6865(2) 0.0519(11) Uani 1 1 d . . . . .
H2 H 0.9740 1.2526 0.7113 0.062 Uiso 1 1 calc R U . . .
C3 C 0.92248(19) 1.0082(6) 0.7054(2) 0.0473(11) Uani 1 1 d . . . . .
C4 C 0.90488(18) 0.8607(6) 0.65323(19) 0.0403(10) Uani 1 1 d . . . . .
C5 C 0.87068(17) 0.6919(6) 0.64303(18) 0.0401(10) Uani 1 1 d . . . . .
C6 C 0.85950(18) 0.5648(6) 0.58648(19) 0.0421(10) Uani 1 1 d . . . . .
C7 C 0.82601(19) 0.3885(6) 0.5645(2) 0.0483(11) Uani 1 1 d . . . . .
C8 C 0.8307(2) 0.3308(6) 0.5042(2) 0.0539(12) Uani 1 1 d . . . . .
H8 H 0.8133 0.2200 0.4779 0.065 Uiso 1 1 calc R U . . .
C9 C 0.86618(19) 0.4664(7) 0.4887(2) 0.0500(11) Uani 1 1 d . . . . .
C10 C 0.8822(2) 0.4649(8) 0.4274(2) 0.0696(15) Uani 1 1 d . . . . .
H10A H 0.8590 0.5609 0.3938 0.104 Uiso 1 1 calc R U . . .
H10B H 0.8747 0.3369 0.4062 0.104 Uiso 1 1 calc R U . . .
H10C H 0.9232 0.4960 0.4426 0.104 Uiso 1 1 calc R U . . .
C11 C 0.7910(2) 0.2821(7) 0.5976(2) 0.0617(13) Uani 1 1 d . . . . .
H11A H 0.8135 0.2756 0.6473 0.093 Uiso 1 1 calc R U . . .
H11B H 0.7824 0.1514 0.5789 0.093 Uiso 1 1 calc R U . . .
H11C H 0.7549 0.3514 0.5878 0.093 Uiso 1 1 calc R U . . .
C12 C 0.9083(2) 1.0325(7) 0.7679(2) 0.0623(13) Uani 1 1 d . . . . .
H12A H 0.9256 1.1520 0.7918 0.093 Uiso 1 1 calc R U . . .
H12B H 0.9238 0.9230 0.7989 0.093 Uiso 1 1 calc R U . . .
H12C H 0.8663 1.0380 0.7529 0.093 Uiso 1 1 calc R U . . .
C13 C 0.9889(2) 1.1719(7) 0.5844(2) 0.0648(13) Uani 1 1 d . . . . .
H13A H 1.0248 1.1027 0.5929 0.097 Uiso 1 1 calc R U . . .
H13B H 0.9977 1.3063 0.5988 0.097 Uiso 1 1 calc R U . . .
H13C H 0.9637 1.1673 0.5354 0.097 Uiso 1 1 calc R U . . .
C14 C 0.84366(19) 0.6496(6) 0.69350(19) 0.0426(10) Uani 1 1 d . . . . .
C15 C 0.8749(2) 0.5588(6) 0.7569(2) 0.0492(11) Uani 1 1 d . . . . .
H15 H 0.9134 0.5182 0.7687 0.059 Uiso 1 1 calc R U . . .
C16 C 0.8486(2) 0.5288(7) 0.8022(2) 0.0609(13) Uani 1 1 d . . . . .
H16 H 0.8711 0.4722 0.8454 0.073 Uiso 1 1 calc R U . . .
C17 C 0.7635(2) 0.6593(8) 0.7266(3) 0.0702(15) Uani 1 1 d . . . . .
H17 H 0.7245 0.6933 0.7152 0.084 Uiso 1 1 calc R U . . .
C18 C 0.7865(2) 0.6994(7) 0.6782(2) 0.0575(12) Uani 1 1 d . . . . .
H18 H 0.7634 0.7592 0.6359 0.069 Uiso 1 1 calc R U . . .
B2 B 0.9225(2) 0.7833(8) 0.5406(2) 0.0469(12) Uani 1 1 d . . . . .
F3 F 0.52335(12) 0.7125(5) 0.07456(13) 0.0801(9) Uani 1 1 d . . . . .
F4 F 0.60336(15) 0.8856(4) 0.08354(14) 0.0807(9) Uani 1 1 d . . . . .
N4 N 0.61750(15) 0.6131(5) 0.16149(16) 0.0473(9) Uani 1 1 d . . . . .
N5 N 0.56939(14) 0.9201(5) 0.17449(16) 0.0440(9) Uani 1 1 d . . . . .
N6 N 0.7139(2) 0.7075(7) 0.49945(19) 0.0729(13) Uani 1 1 d . . . . .
C19 C 0.6369(2) 0.4664(7) 0.1341(2) 0.0565(12) Uani 1 1 d . . . . .
C20 C 0.6738(2) 0.3458(7) 0.1888(2) 0.0648(13) Uani 1 1 d . . . . .
H20 H 0.6922 0.2320 0.1834 0.078 Uiso 1 1 calc R U . . .
C21 C 0.6783(2) 0.4222(6) 0.2515(2) 0.0528(11) Uani 1 1 d . . . . .
C22 C 0.64222(18) 0.5939(6) 0.2341(2) 0.0437(10) Uani 1 1 d . . . . .
C23 C 0.63061(17) 0.7327(6) 0.27582(19) 0.0406(10) Uani 1 1 d . . . . .
C24 C 0.59387(18) 0.8931(6) 0.24715(19) 0.0425(10) Uani 1 1 d . . . . .
C25 C 0.57464(19) 1.0491(6) 0.2775(2) 0.0449(10) Uani 1 1 d . . . . .
C26 C 0.5398(2) 1.1670(7) 0.2229(2) 0.0592(12) Uani 1 1 d . . . . .
H26 H 0.5209 1.2812 0.2269 0.071 Uiso 1 1 calc R U . . .
C27 C 0.5374(2) 1.0865(7) 0.1604(2) 0.0548(12) Uani 1 1 d . . . . .
C28 C 0.5060(2) 1.1632(8) 0.0876(2) 0.0715(15) Uani 1 1 d . . . . .
H28A H 0.5324 1.1649 0.0646 0.107 Uiso 1 1 calc R U . . .
H28B H 0.4922 1.2941 0.0892 0.107 Uiso 1 1 calc R U . . .
H28C H 0.4730 1.0797 0.0621 0.107 Uiso 1 1 calc R U . . .
C29 C 0.5868(2) 1.0856(7) 0.3531(2) 0.0613(13) Uani 1 1 d . . . . .
H29A H 0.5787 0.9683 0.3730 0.092 Uiso 1 1 calc R U . . .
H29B H 0.5622 1.1904 0.3562 0.092 Uiso 1 1 calc R U . . .
H29C H 0.6274 1.1213 0.3782 0.092 Uiso 1 1 calc R U . . .
C30 C 0.7149(2) 0.3379(7) 0.3218(2) 0.0652(14) Uani 1 1 d . . . . .
H30A H 0.7320 0.2161 0.3162 0.098 Uiso 1 1 calc R U . . .
H30B H 0.6906 0.3146 0.3468 0.098 Uiso 1 1 calc R U . . .
H30C H 0.7456 0.4287 0.3477 0.098 Uiso 1 1 calc R U . . .
C31 C 0.6205(3) 0.4419(8) 0.0571(2) 0.0811(17) Uani 1 1 d . . . . .
H31A H 0.5802 0.4793 0.0315 0.122 Uiso 1 1 calc R U . . .
H31B H 0.6256 0.3070 0.0474 0.122 Uiso 1 1 calc R U . . .
H31C H 0.6454 0.5238 0.0433 0.122 Uiso 1 1 calc R U . . .
C32 C 0.66024(18) 0.7170(6) 0.35372(19) 0.0418(10) Uani 1 1 d . . . . .
C33 C 0.6338(2) 0.6214(7) 0.3914(2) 0.0546(12) Uani 1 1 d . . . . .
H33 H 0.5979 0.5578 0.3690 0.065 Uiso 1 1 calc R U . . .
C34 C 0.6625(3) 0.6230(8) 0.4640(3) 0.0683(14) Uani 1 1 d . . . . .
H34 H 0.6443 0.5603 0.4893 0.082 Uiso 1 1 calc R U . . .
C35 C 0.7389(2) 0.7924(7) 0.4614(2) 0.0598(13) Uani 1 1 d . . . . .
H35 H 0.7755 0.8512 0.4852 0.072 Uiso 1 1 calc R U . . .
C36 C 0.71511(19) 0.8003(6) 0.3899(2) 0.0472(11) Uani 1 1 d . . . . .
H36 H 0.7353 0.8601 0.3663 0.057 Uiso 1 1 calc R U . . .
B1 B 0.5777(2) 0.7852(8) 0.1208(2) 0.0493(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B2 1.387(6) . ?
F2 B2 1.378(5) . ?
N1 C1 1.350(5) . ?
N1 C4 1.404(5) . ?
N1 B2 1.536(6) . ?
N2 C6 1.396(5) . ?
N2 C9 1.338(5) . ?
N2 B2 1.537(6) . ?
N3 C16 1.324(6) . ?
N3 C17 1.334(6) . ?
C1 C2 1.384(6) . ?
C1 C13 1.493(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(6) . ?
C3 C4 1.415(6) . ?
C3 C12 1.496(5) . ?
C4 C5 1.393(5) . ?
C5 C6 1.399(5) . ?
C5 C14 1.494(5) . ?
C6 C7 1.426(6) . ?
C7 C8 1.371(5) . ?
C7 C11 1.502(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.402(6) . ?
C9 C10 1.493(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.380(5) . ?
C14 C18 1.367(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.369(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.379(6) . ?
C18 H18 0.9300 . ?
F3 B1 1.394(6) . ?
F4 B1 1.373(5) . ?
N4 C19 1.336(5) . ?
N4 C22 1.394(5) . ?
N4 B1 1.545(6) . ?
N5 C24 1.401(5) . ?
N5 C27 1.345(5) . ?
N5 B1 1.530(6) . ?
N6 C34 1.319(7) . ?
N6 C35 1.326(6) . ?
C19 C20 1.403(6) . ?
C19 C31 1.501(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(6) . ?
C21 C22 1.426(6) . ?
C21 C30 1.494(6) . ?
C22 C23 1.394(5) . ?
C23 C24 1.393(6) . ?
C23 C32 1.494(5) . ?
C24 C25 1.416(5) . ?
C25 C26 1.376(6) . ?
C25 C29 1.506(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.398(6) . ?
C27 C28 1.495(6) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.379(5) . ?
C32 C36 1.384(6) . ?
C33 H33 0.9300 . ?
C33 C34 1.391(6) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C35 C36 1.368(6) . ?
C36 H36 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
C1 N1 C4 107.8(3) . . ?
C1 N1 B2 126.1(3) . . ?
C4 N1 B2 126.1(3) . . ?
C6 N2 B2 125.7(3) . . ?
C9 N2 C6 108.7(3) . . ?
C9 N2 B2 125.6(3) . . ?
C16 N3 C17 115.3(4) . . ?
N1 C1 C2 109.2(4) . . ?
N1 C1 C13 122.2(4) . . ?
C2 C1 C13 128.5(4) . . ?
C1 C2 H2 125.5 . . ?
C1 C2 C3 109.1(4) . . ?
C3 C2 H2 125.5 . . ?
C2 C3 C4 105.7(3) . . ?
C2 C3 C12 124.1(4) . . ?
C4 C3 C12 130.1(4) . . ?
N1 C4 C3 108.1(3) . . ?
C5 C4 N1 119.0(3) . . ?
C5 C4 C3 132.9(4) . . ?
C4 C5 C6 122.5(3) . . ?
C4 C5 C14 118.3(3) . . ?
C6 C5 C14 119.2(4) . . ?
N2 C6 C5 119.6(4) . . ?
N2 C6 C7 107.4(3) . . ?
C5 C6 C7 133.0(4) . . ?
C6 C7 C11 128.9(4) . . ?
C8 C7 C6 106.3(4) . . ?
C8 C7 C11 124.8(4) . . ?
C7 C8 H8 125.6 . . ?
C7 C8 C9 108.8(4) . . ?
C9 C8 H8 125.6 . . ?
N2 C9 C8 108.8(3) . . ?
N2 C9 C10 123.8(4) . . ?
C8 C9 C10 127.4(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C5 121.9(4) . . ?
C18 C14 C5 120.8(4) . . ?
C18 C14 C15 117.3(4) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(4) . . ?
C16 C15 H15 120.2 . . ?
N3 C16 C15 124.3(4) . . ?
N3 C16 H16 117.8 . . ?
C15 C16 H16 117.8 . . ?
N3 C17 H17 117.7 . . ?
N3 C17 C18 124.7(5) . . ?
C18 C17 H17 117.7 . . ?
C14 C18 C17 118.8(4) . . ?
C14 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
F1 B2 N1 109.6(4) . . ?
F1 B2 N2 109.5(4) . . ?
F2 B2 F1 109.5(3) . . ?
F2 B2 N1 111.0(4) . . ?
F2 B2 N2 110.1(4) . . ?
N1 B2 N2 107.1(3) . . ?
C19 N4 C22 108.9(4) . . ?
C19 N4 B1 126.2(3) . . ?
C22 N4 B1 124.8(3) . . ?
C24 N5 B1 126.2(4) . . ?
C27 N5 C24 107.8(3) . . ?
C27 N5 B1 126.0(3) . . ?
C34 N6 C35 115.9(4) . . ?
N4 C19 C20 108.4(4) . . ?
N4 C19 C31 123.9(5) . . ?
C20 C19 C31 127.7(4) . . ?
C19 C20 H20 125.4 . . ?
C21 C20 C19 109.3(4) . . ?
C21 C20 H20 125.4 . . ?
C20 C21 C22 105.6(4) . . ?
C20 C21 C30 125.2(4) . . ?
C22 C21 C30 129.2(4) . . ?
N4 C22 C21 107.8(4) . . ?
C23 C22 N4 120.5(4) . . ?
C23 C22 C21 131.6(4) . . ?
C22 C23 C32 119.9(4) . . ?
C24 C23 C22 121.9(3) . . ?
C24 C23 C32 118.1(3) . . ?
N5 C24 C25 108.2(4) . . ?
C23 C24 N5 119.3(3) . . ?
C23 C24 C25 132.6(4) . . ?
C24 C25 C29 129.4(4) . . ?
C26 C25 C24 106.1(4) . . ?
C26 C25 C29 124.5(4) . . ?
C25 C26 H26 125.6 . . ?
C25 C26 C27 108.7(4) . . ?
C27 C26 H26 125.6 . . ?
N5 C27 C26 109.2(4) . . ?
N5 C27 C28 122.3(4) . . ?
C26 C27 C28 128.5(4) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C29 H29A 109.5 . . ?
C25 C29 H29B 109.5 . . ?
C25 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C21 C30 H30A 109.5 . . ?
C21 C30 H30B 109.5 . . ?
C21 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C19 C31 H31A 109.5 . . ?
C19 C31 H31B 109.5 . . ?
C19 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C23 121.4(4) . . ?
C33 C32 C36 118.3(4) . . ?
C36 C32 C23 120.4(4) . . ?
C32 C33 H33 121.0 . . ?
C32 C33 C34 118.0(5) . . ?
C34 C33 H33 121.0 . . ?
N6 C34 C33 124.4(5) . . ?
N6 C34 H34 117.8 . . ?
C33 C34 H34 117.8 . . ?
N6 C35 H35 117.5 . . ?
N6 C35 C36 125.0(5) . . ?
C36 C35 H35 117.5 . . ?
C32 C36 H36 120.9 . . ?
C35 C36 C32 118.3(4) . . ?
C35 C36 H36 120.9 . . ?
F3 B1 N4 109.6(4) . . ?
F3 B1 N5 109.8(4) . . ?
F4 B1 F3 109.1(4) . . ?
F4 B1 N4 110.4(4) . . ?
F4 B1 N5 110.7(4) . . ?
N5 B1 N4 107.3(3) . . ?

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 -1.7(5) . . . . ?
N1 C4 C5 C6 0.4(6) . . . . ?
N1 C4 C5 C14 -177.7(3) . . . . ?
N2 C6 C7 C8 -0.4(5) . . . . ?
N2 C6 C7 C11 -179.5(4) . . . . ?
N3 C17 C18 C14 0.4(8) . . . . ?
C1 N1 C4 C3 -1.7(4) . . . . ?
C1 N1 C4 C5 178.4(4) . . . . ?
C1 N1 B2 F1 63.0(5) . . . . ?
C1 N1 B2 F2 -58.1(6) . . . . ?
C1 N1 B2 N2 -178.3(4) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C1 C2 C3 C12 -177.5(4) . . . . ?
C2 C3 C4 N1 0.7(4) . . . . ?
C2 C3 C4 C5 -179.4(4) . . . . ?
C3 C4 C5 C6 -179.5(4) . . . . ?
C3 C4 C5 C14 2.4(7) . . . . ?
C4 N1 C1 C2 2.1(5) . . . . ?
C4 N1 C1 C13 -179.0(4) . . . . ?
C4 N1 B2 F1 -116.9(4) . . . . ?
C4 N1 B2 F2 122.0(4) . . . . ?
C4 N1 B2 N2 1.8(5) . . . . ?
C4 C5 C6 N2 0.5(6) . . . . ?
C4 C5 C6 C7 -179.0(4) . . . . ?
C4 C5 C14 C15 -82.6(5) . . . . ?
C4 C5 C14 C18 97.7(5) . . . . ?
C5 C6 C7 C8 179.1(4) . . . . ?
C5 C6 C7 C11 0.0(8) . . . . ?
C5 C14 C15 C16 178.0(4) . . . . ?
C5 C14 C18 C17 -179.4(4) . . . . ?
C6 N2 C9 C8 -0.4(5) . . . . ?
C6 N2 C9 C10 178.4(4) . . . . ?
C6 N2 B2 F1 117.9(4) . . . . ?
C6 N2 B2 F2 -121.7(4) . . . . ?
C6 N2 B2 N1 -0.9(5) . . . . ?
C6 C5 C14 C15 99.2(5) . . . . ?
C6 C5 C14 C18 -80.5(5) . . . . ?
C6 C7 C8 C9 0.1(5) . . . . ?
C7 C8 C9 N2 0.2(5) . . . . ?
C7 C8 C9 C10 -178.6(5) . . . . ?
C9 N2 C6 C5 -179.1(4) . . . . ?
C9 N2 C6 C7 0.5(4) . . . . ?
C9 N2 B2 F1 -63.4(5) . . . . ?
C9 N2 B2 F2 57.1(5) . . . . ?
C9 N2 B2 N1 177.9(4) . . . . ?
C11 C7 C8 C9 179.3(4) . . . . ?
C12 C3 C4 N1 178.6(4) . . . . ?
C12 C3 C4 C5 -1.5(8) . . . . ?
C13 C1 C2 C3 179.5(4) . . . . ?
C14 C5 C6 N2 178.6(3) . . . . ?
C14 C5 C6 C7 -0.9(7) . . . . ?
C14 C15 C16 N3 2.6(7) . . . . ?
C15 C14 C18 C17 0.9(7) . . . . ?
C16 N3 C17 C18 -0.3(8) . . . . ?
C17 N3 C16 C15 -1.2(7) . . . . ?
C18 C14 C15 C16 -2.3(6) . . . . ?
B2 N1 C1 C2 -177.8(4) . . . . ?
B2 N1 C1 C13 1.1(7) . . . . ?
B2 N1 C4 C3 178.2(4) . . . . ?
B2 N1 C4 C5 -1.7(6) . . . . ?
B2 N2 C6 C5 -0.1(6) . . . . ?
B2 N2 C6 C7 179.4(4) . . . . ?
B2 N2 C9 C8 -179.4(4) . . . . ?
B2 N2 C9 C10 -0.6(7) . . . . ?
N4 C19 C20 C21 -1.4(6) . . . . ?
N4 C22 C23 C24 0.7(6) . . . . ?
N4 C22 C23 C32 -176.3(4) . . . . ?
N5 C24 C25 C26 -0.6(5) . . . . ?
N5 C24 C25 C29 178.0(4) . . . . ?
N6 C35 C36 C32 1.2(7) . . . . ?
C19 N4 C22 C21 -0.9(5) . . . . ?
C19 N4 C22 C23 177.9(4) . . . . ?
C19 N4 B1 F3 63.2(5) . . . . ?
C19 N4 B1 F4 -57.0(6) . . . . ?
C19 N4 B1 N5 -177.7(4) . . . . ?
C19 C20 C21 C22 0.8(5) . . . . ?
C19 C20 C21 C30 -178.4(4) . . . . ?
C20 C21 C22 N4 0.0(5) . . . . ?
C20 C21 C22 C23 -178.5(4) . . . . ?
C21 C22 C23 C24 179.1(4) . . . . ?
C21 C22 C23 C32 2.1(7) . . . . ?
C22 N4 C19 C20 1.4(5) . . . . ?
C22 N4 C19 C31 -178.6(4) . . . . ?
C22 N4 B1 F3 -121.4(4) . . . . ?
C22 N4 B1 F4 118.4(4) . . . . ?
C22 N4 B1 N5 -2.3(6) . . . . ?
C22 C23 C24 N5 -2.2(6) . . . . ?
C22 C23 C24 C25 178.7(4) . . . . ?
C22 C23 C32 C33 -93.7(5) . . . . ?
C22 C23 C32 C36 86.8(5) . . . . ?
C23 C24 C25 C26 178.6(4) . . . . ?
C23 C24 C25 C29 -2.8(8) . . . . ?
C23 C32 C33 C34 -176.2(4) . . . . ?
C23 C32 C36 C35 176.1(4) . . . . ?
C24 N5 C27 C26 -1.1(5) . . . . ?
C24 N5 C27 C28 178.6(4) . . . . ?
C24 N5 B1 F3 119.7(4) . . . . ?
C24 N5 B1 F4 -119.9(4) . . . . ?
C24 N5 B1 N4 0.6(6) . . . . ?
C24 C23 C32 C33 89.2(5) . . . . ?
C24 C23 C32 C36 -90.3(5) . . . . ?
C24 C25 C26 C27 -0.1(5) . . . . ?
C25 C26 C27 N5 0.8(5) . . . . ?
C25 C26 C27 C28 -179.0(5) . . . . ?
C27 N5 C24 C23 -178.2(4) . . . . ?
C27 N5 C24 C25 1.1(5) . . . . ?
C27 N5 B1 F3 -60.7(6) . . . . ?
C27 N5 B1 F4 59.7(6) . . . . ?
C27 N5 B1 N4 -179.7(4) . . . . ?
C29 C25 C26 C27 -178.8(4) . . . . ?
C30 C21 C22 N4 179.2(4) . . . . ?
C30 C21 C22 C23 0.6(8) . . . . ?
C31 C19 C20 C21 178.6(5) . . . . ?
C32 C23 C24 N5 174.8(4) . . . . ?
C32 C23 C24 C25 -4.3(7) . . . . ?
C32 C33 C34 N6 -1.1(8) . . . . ?
C33 C32 C36 C35 -3.4(6) . . . . ?
C34 N6 C35 C36 1.0(7) . . . . ?
C35 N6 C34 C33 -1.1(8) . . . . ?
C36 C32 C33 C34 3.3(6) . . . . ?
B1 N4 C19 C20 177.4(4) . . . . ?
B1 N4 C19 C31 -2.6(7) . . . . ?
B1 N4 C22 C21 -177.0(4) . . . . ?
B1 N4 C22 C23 1.8(6) . . . . ?
B1 N5 C24 C23 1.5(6) . . . . ?
B1 N5 C24 C25 -179.2(4) . . . . ?
B1 N5 C27 C26 179.2(4) . . . . ?
B1 N5 C27 C28 -1.1(7) . . . . ?

_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_20gtu106_bc_eo_78_0ma
_database_code_depnum_ccdc_archive 'CCDC 2011926'
loop_
_audit_author_name
_audit_author_address
'Yunus Zorlu' 'Gebze Technical University'
_audit_update_record             
;
2020-11-30 deposited with the CCDC.	2020-12-07 downloaded from the CCDC.
;
_audit_creation_date             2020-11-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 B F2 I2 N3'
_chemical_formula_sum            'C18 H16 B F2 I2 N3'
_chemical_formula_weight         576.95
_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'
I I -0.4742 1.8119 '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      orthorhombic
_space_group_IT_number           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z-1/2'
'x+1/2, -y+1/2, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   16.724(2)
_cell_length_b                   15.302(2)
_cell_length_c                   7.6345(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1953.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5290
_cell_measurement_temperature    119.91
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   0.844
_shelx_estimated_absorpt_T_min   0.579
_exptl_absorpt_coefficient_mu    3.244
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1352 before and 0.0758 after correction.
The Ratio of minimum to maximum transmission is 0.5345.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.961
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.054
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7350
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.984
_diffrn_reflns_theta_max         24.984
_diffrn_reflns_theta_min         3.221
_diffrn_ambient_temperature      119.91
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                923
_reflns_number_total             967
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.695
_refine_diff_density_min         -1.721
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       0.0008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     86
_refine_ls_number_reflns         967
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+4.8540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0798
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H6A(0.5) H6B(0.5) H6C(0.5) H7A(0.5) H7B(0.5) H7C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10)
3.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.82392(2) 0.43500(2) 0.750000 0.0369(2) Uani 1 2 d S T P . .
F1 F 0.500000 0.59033(14) 0.8970(3) 0.0204(5) Uani 1 2 d S T P . .
N1 N 0.5744(2) 0.4763(2) 0.750000 0.0145(7) Uani 1 2 d S T P . .
N2 N 0.500000 0.0606(3) 0.750000 0.0223(12) Uani 1 4 d S T P . .
C1 C 0.6508(3) 0.5029(3) 0.750000 0.0180(8) Uani 1 2 d S T P . .
C2 C 0.7004(3) 0.4286(3) 0.750000 0.0183(9) Uani 1 2 d S T P . .
C3 C 0.6530(3) 0.3543(3) 0.750000 0.0162(8) Uani 1 2 d S T P . .
C4 C 0.5724(2) 0.3856(2) 0.750000 0.0135(8) Uani 1 2 d S T P . .
C5 C 0.500000 0.3416(3) 0.750000 0.0124(10) Uani 1 4 d S T P . .
C6 C 0.6752(3) 0.5971(3) 0.750000 0.0289(12) Uani 1 2 d S T P . .
H6A H 0.634587 0.631787 0.688890 0.043 Uiso 0.5 1 calc R U P A -1
H6B H 0.726666 0.603326 0.690089 0.043 Uiso 0.5 1 calc R U P A -1
H6C H 0.680170 0.617697 0.871021 0.043 Uiso 0.5 1 calc R U P A -1
C7 C 0.6837(3) 0.2616(3) 0.750000 0.0251(10) Uani 1 2 d S T P . .
H7A H 0.740333 0.261250 0.717256 0.038 Uiso 0.5 1 calc R U P B -1
H7B H 0.653118 0.226834 0.665472 0.038 Uiso 0.5 1 calc R U P B -1
H7C H 0.677469 0.236444 0.867272 0.038 Uiso 0.5 1 calc R U P B -1
C8 C 0.500000 0.2436(3) 0.750000 0.0130(10) Uani 1 4 d S T P . .
C9 C 0.500000 0.1979(2) 0.5947(5) 0.0198(8) Uani 1 2 d S T P . .
H9 H 0.500000 0.227720 0.485516 0.024 Uiso 1 2 calc R U P . .
C10 C 0.500000 0.1063(3) 0.6012(6) 0.0226(9) Uani 1 2 d S T P . .
H10 H 0.500000 0.075083 0.493700 0.027 Uiso 1 2 calc R U P . .
B1 B 0.500000 0.5372(4) 0.750000 0.0166(13) Uani 1 4 d S T P . .


_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
I1 C2 2.067(5) . ?
F1 B1 1.385(4) . ?
N1 C1 1.342(6) . ?
N1 C4 1.389(5) . ?
N1 B1 1.554(5) . ?
N2 C10 1.334(5) . ?
N2 C10 1.334(5) 10_557 ?
C1 C2 1.408(6) . ?
C1 C6 1.497(6) . ?
C2 C3 1.386(6) . ?
C3 C4 1.432(6) . ?
C3 C7 1.508(6) . ?
C4 C5 1.385(5) . ?
C5 C8 1.500(7) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.377(5) 10_557 ?
C8 C9 1.377(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.402(5) . ?
C10 H10 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 109.0(3) . . ?
C1 N1 B1 125.5(3) . . ?
C4 N1 B1 125.5(3) . . ?
C10 N2 C10 116.8(5) . 10_557 ?
N1 C1 C2 108.5(3) . . ?
N1 C1 C6 123.5(4) . . ?
C2 C1 C6 128.1(4) . . ?
C1 C2 I1 123.4(3) . . ?
C3 C2 I1 127.6(3) . . ?
C3 C2 C1 109.0(4) . . ?
C2 C3 C4 105.3(4) . . ?
C2 C3 C7 125.3(4) . . ?
C4 C3 C7 129.4(4) . . ?
N1 C4 C3 108.2(3) . . ?
C5 C4 N1 120.4(3) . . ?
C5 C4 C3 131.4(4) . . ?
C4 C5 C4 121.9(5) 3_656 . ?
C4 C5 C8 119.1(2) . . ?
C4 C5 C8 119.1(2) 3_656 . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C5 120.5(2) . . ?
C9 C8 C5 120.5(2) 10_557 . ?
C9 C8 C9 119.0(5) 10_557 . ?
C8 C9 H9 120.8 . . ?
C8 C9 C10 118.5(4) . . ?
C10 C9 H9 120.8 . . ?
N2 C10 C9 123.7(4) . . ?
N2 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
F1 B1 F1 108.2(5) . 10_557 ?
F1 B1 N1 110.59(8) . . ?
F1 B1 N1 110.59(8) 10_557 3_656 ?
F1 B1 N1 110.59(8) 10_557 . ?
F1 B1 N1 110.59(8) . 3_656 ?
N1 B1 N1 106.3(4) 3_656 . ?

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
I1 C2 C3 C4 180.0 . . . . ?
I1 C2 C3 C7 0.0 . . . . ?
N1 C1 C2 I1 180.0 . . . . ?
N1 C1 C2 C3 0.0 . . . . ?
N1 C4 C5 C4 0.0 . . . 3_656 ?
N1 C4 C5 C8 180.0 . . . . ?
C1 N1 C4 C3 0.0 . . . . ?
C1 N1 C4 C5 180.0 . . . . ?
C1 N1 B1 F1 -59.9(3) . . . . ?
C1 N1 B1 F1 59.9(3) . . . 10_557 ?
C1 N1 B1 N1 180.0 . . . 3_656 ?
C1 C2 C3 C4 0.0 . . . . ?
C1 C2 C3 C7 180.0 . . . . ?
C2 C3 C4 N1 0.0 . . . . ?
C2 C3 C4 C5 180.0 . . . . ?
C3 C4 C5 C4 180.0 . . . 3_656 ?
C3 C4 C5 C8 0.0 . . . . ?
C4 N1 C1 C2 0.0 . . . . ?
C4 N1 C1 C6 180.0 . . . . ?
C4 N1 B1 F1 -120.1(3) . . . 10_557 ?
C4 N1 B1 F1 120.1(3) . . . . ?
C4 N1 B1 N1 0.0 . . . 3_656 ?
C4 C5 C8 C9 -90.000 . . . . ?
C4 C5 C8 C9 90.000 . . . 10_557 ?
C4 C5 C8 C9 -90.000 3_656 . . 10_557 ?
C4 C5 C8 C9 90.000 3_656 . . . ?
C5 C8 C9 C10 180.000(1) . . . . ?
C6 C1 C2 I1 0.0 . . . . ?
C6 C1 C2 C3 180.0 . . . . ?
C7 C3 C4 N1 180.0 . . . . ?
C7 C3 C4 C5 0.0 . . . . ?
C8 C9 C10 N2 0.000(1) . . . . ?
C9 C8 C9 C10 0.000(1) 10_557 . . . ?
C10 N2 C10 C9 0.000(1) 10_557 . . . ?
B1 N1 C1 C2 180.0 . . . . ?
B1 N1 C1 C6 0.0 . . . . ?
B1 N1 C4 C3 180.0 . . . . ?
B1 N1 C4 C5 0.0 . . . . ?

_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_19gtu183
_database_code_depnum_ccdc_archive 'CCDC 2011925'
loop_
_audit_author_name
_audit_author_address
'Yunus Zorlu' 'Gebze Technical University'
_audit_update_record             
;
2020-06-24 deposited with the CCDC.	2020-12-07 downloaded from the CCDC.
;
_audit_creation_date             2020-05-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 B F2 I N3'
_chemical_formula_sum            'C18 H17 B F2 I N3'
_chemical_formula_weight         451.05
_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'
I I -0.4742 1.8119 '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/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                   14.9264(12)
_cell_length_b                   11.4332(9)
_cell_length_c                   10.9861(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.745(4)
_cell_angle_gamma                90
_cell_volume                     1785.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3451
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.45
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   0.848
_shelx_estimated_absorpt_T_min   0.540
_exptl_absorpt_coefficient_mu    1.818
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5 (Bruker,2014/5)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.387
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.094
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9432
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.021
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_min         2.286
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2763
_reflns_number_total             3148
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+1.5142P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0769
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C2(H2), C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.14764(2) 1.07418(2) 0.16081(2) 0.05180(11) Uani 1 1 d . . . . .
F1 F 0.47841(12) 0.80049(16) 0.49916(19) 0.0517(5) Uani 1 1 d . . . . .
F2 F 0.38538(15) 0.83086(17) 0.62398(17) 0.0553(5) Uani 1 1 d . . . . .
N1 N 0.38328(17) 0.6414(2) 0.5290(2) 0.0328(5) Uani 1 1 d . . . . .
N2 N 0.31182(17) 0.81337(19) 0.3973(2) 0.0318(5) Uani 1 1 d . . . . .
C8 C 0.2118(2) 0.9233(2) 0.2508(3) 0.0364(7) Uani 1 1 d . . . . .
C9 C 0.2928(2) 0.9240(2) 0.3562(3) 0.0329(6) Uani 1 1 d . . . . .
C4 C 0.3180(2) 0.5702(2) 0.4418(3) 0.0354(7) Uani 1 1 d . . . . .
C6 C 0.2450(2) 0.7401(2) 0.3169(3) 0.0339(6) Uani 1 1 d . . . . .
C5 C 0.2510(2) 0.6185(2) 0.3395(3) 0.0330(6) Uani 1 1 d . . . . .
C7 C 0.1815(2) 0.8087(3) 0.2232(3) 0.0374(7) Uani 1 1 d . . . . .
C14 C 0.1841(2) 0.5382(3) 0.2471(3) 0.0381(7) Uani 1 1 d . . . . .
C1 C 0.4407(2) 0.5738(3) 0.6182(3) 0.0406(7) Uani 1 1 d . . . . .
C10 C 0.3528(2) 1.0251(3) 0.4141(3) 0.0449(8) Uani 1 1 d . . . . .
H10A H 0.4117 0.9975 0.4701 0.067 Uiso 1 1 calc R U . . .
H10B H 0.3215 1.0712 0.4619 0.067 Uiso 1 1 calc R U . . .
H10C H 0.3639 1.0721 0.3478 0.067 Uiso 1 1 calc R U . . .
C3 C 0.3387(3) 0.4517(3) 0.4833(3) 0.0428(8) Uani 1 1 d . . . . .
N3 N 0.0698(3) 0.3757(3) 0.0825(3) 0.0687(10) Uani 1 1 d . . . . .
C18 C 0.1040(3) 0.4969(3) 0.2688(4) 0.0532(9) Uani 1 1 d . . . . .
H18 H 0.0865 0.5224 0.3387 0.064 Uiso 1 1 calc R U . . .
C2 C 0.4147(3) 0.4567(3) 0.5923(3) 0.0478(8) Uani 1 1 d . . . . .
H2 H 0.4439 0.3928 0.6406 0.057 Uiso 1 1 calc R U . . .
C15 C 0.2043(3) 0.5007(3) 0.1392(3) 0.0497(9) Uani 1 1 d . . . . .
H15 H 0.2566 0.5291 0.1196 0.060 Uiso 1 1 calc R U . . .
C13 C 0.5185(3) 0.6199(4) 0.7267(3) 0.0533(9) Uani 1 1 d . . . . .
H13A H 0.5501 0.6816 0.6969 0.080 Uiso 1 1 calc R U . . .
H13B H 0.5622 0.5581 0.7620 0.080 Uiso 1 1 calc R U . . .
H13C H 0.4934 0.6497 0.7912 0.080 Uiso 1 1 calc R U . . .
C11 C 0.0998(3) 0.7716(3) 0.1129(4) 0.0621(11) Uani 1 1 d . . . . .
H11A H 0.0644 0.8392 0.0742 0.093 Uiso 1 1 calc R U . . .
H11B H 0.0603 0.7199 0.1427 0.093 Uiso 1 1 calc R U . . .
H11C H 0.1224 0.7317 0.0511 0.093 Uiso 1 1 calc R U . . .
B1 B 0.3924(2) 0.7747(3) 0.5161(3) 0.0351(8) Uani 1 1 d . . . . .
C12 C 0.2914(3) 0.3406(3) 0.4264(4) 0.0616(10) Uani 1 1 d . . . . .
H12A H 0.2283 0.3396 0.4313 0.092 Uiso 1 1 calc R U . . .
H12B H 0.3256 0.2752 0.4728 0.092 Uiso 1 1 calc R U . . .
H12C H 0.2899 0.3357 0.3386 0.092 Uiso 1 1 calc R U . . .
C16 C 0.1453(3) 0.4201(3) 0.0606(4) 0.0651(11) Uani 1 1 d . . . . .
H16 H 0.1596 0.3955 -0.0121 0.078 Uiso 1 1 calc R U . . .
C17 C 0.0500(3) 0.4165(4) 0.1837(5) 0.0678(12) Uani 1 1 d . . . . .
H17 H -0.0043 0.3891 0.1989 0.081 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
I1 C8 2.072(3) . ?
F1 B1 1.383(4) . ?
F2 B1 1.380(4) . ?
N1 C4 1.400(4) . ?
N1 C1 1.334(4) . ?
N1 B1 1.540(4) . ?
N2 C9 1.343(3) . ?
N2 C6 1.392(3) . ?
N2 B1 1.546(4) . ?
C8 C9 1.396(4) . ?
C8 C7 1.390(4) . ?
C9 C10 1.481(4) . ?
C4 C5 1.371(4) . ?
C4 C3 1.433(4) . ?
C6 C5 1.411(4) . ?
C6 C7 1.407(4) . ?
C5 C14 1.501(4) . ?
C7 C11 1.494(4) . ?
C14 C18 1.372(5) . ?
C14 C15 1.378(4) . ?
C1 C2 1.399(5) . ?
C1 C13 1.484(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C3 C2 1.376(5) . ?
C3 C12 1.495(5) . ?
N3 C16 1.323(5) . ?
N3 C17 1.320(6) . ?
C18 H18 0.9300 . ?
C18 C17 1.382(5) . ?
C2 H2 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.380(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C16 H16 0.9300 . ?
C17 H17 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
C4 N1 B1 125.1(2) . . ?
C1 N1 C4 108.9(2) . . ?
C1 N1 B1 125.8(3) . . ?
C9 N2 C6 108.4(2) . . ?
C9 N2 B1 125.7(2) . . ?
C6 N2 B1 125.9(2) . . ?
C9 C8 I1 123.3(2) . . ?
C7 C8 I1 127.4(2) . . ?
C7 C8 C9 109.2(2) . . ?
N2 C9 C8 108.3(2) . . ?
N2 C9 C10 123.5(3) . . ?
C8 C9 C10 128.1(3) . . ?
N1 C4 C3 107.1(3) . . ?
C5 C4 N1 120.6(3) . . ?
C5 C4 C3 132.4(3) . . ?
N2 C6 C5 119.1(3) . . ?
N2 C6 C7 108.8(2) . . ?
C7 C6 C5 132.1(3) . . ?
C4 C5 C6 122.1(3) . . ?
C4 C5 C14 118.5(3) . . ?
C6 C5 C14 119.3(3) . . ?
C8 C7 C6 105.2(2) . . ?
C8 C7 C11 125.2(3) . . ?
C6 C7 C11 129.5(3) . . ?
C18 C14 C5 121.9(3) . . ?
C18 C14 C15 118.2(3) . . ?
C15 C14 C5 119.8(3) . . ?
N1 C1 C2 109.2(3) . . ?
N1 C1 C13 123.7(3) . . ?
C2 C1 C13 127.2(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C3 C12 129.9(3) . . ?
C2 C3 C4 106.2(3) . . ?
C2 C3 C12 123.9(3) . . ?
C17 N3 C16 116.0(3) . . ?
C14 C18 H18 121.0 . . ?
C14 C18 C17 118.1(3) . . ?
C17 C18 H18 121.0 . . ?
C1 C2 H2 125.7 . . ?
C3 C2 C1 108.7(3) . . ?
C3 C2 H2 125.7 . . ?
C14 C15 H15 120.6 . . ?
C14 C15 C16 118.7(3) . . ?
C16 C15 H15 120.6 . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
F1 B1 N1 109.6(3) . . ?
F1 B1 N2 109.9(3) . . ?
F2 B1 F1 109.4(3) . . ?
F2 B1 N1 110.4(3) . . ?
F2 B1 N2 110.4(3) . . ?
N1 B1 N2 107.0(2) . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C16 C15 124.0(4) . . ?
N3 C16 H16 118.0 . . ?
C15 C16 H16 118.0 . . ?
N3 C17 C18 124.8(4) . . ?
N3 C17 H17 117.6 . . ?
C18 C17 H17 117.6 . . ?

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
I1 C8 C9 N2 175.3(2) . . . . ?
I1 C8 C9 C10 -7.0(5) . . . . ?
I1 C8 C7 C6 -175.7(2) . . . . ?
I1 C8 C7 C11 6.2(5) . . . . ?
N1 C4 C5 C6 0.5(5) . . . . ?
N1 C4 C5 C14 178.6(3) . . . . ?
N1 C4 C3 C2 -0.1(4) . . . . ?
N1 C4 C3 C12 179.8(3) . . . . ?
N1 C1 C2 C3 0.0(4) . . . . ?
N2 C6 C5 C4 3.0(5) . . . . ?
N2 C6 C5 C14 -175.1(3) . . . . ?
N2 C6 C7 C8 -0.4(3) . . . . ?
N2 C6 C7 C11 177.6(4) . . . . ?
C9 N2 C6 C5 179.0(3) . . . . ?
C9 N2 C6 C7 -0.8(3) . . . . ?
C9 N2 B1 F1 -63.9(4) . . . . ?
C9 N2 B1 F2 56.9(4) . . . . ?
C9 N2 B1 N1 177.1(3) . . . . ?
C9 C8 C7 C6 1.5(4) . . . . ?
C9 C8 C7 C11 -176.7(3) . . . . ?
C4 N1 C1 C2 -0.1(4) . . . . ?
C4 N1 C1 C13 -179.7(3) . . . . ?
C4 N1 B1 F1 -114.5(3) . . . . ?
C4 N1 B1 F2 124.8(3) . . . . ?
C4 N1 B1 N2 4.7(4) . . . . ?
C4 C5 C14 C18 84.1(4) . . . . ?
C4 C5 C14 C15 -93.5(4) . . . . ?
C4 C3 C2 C1 0.0(4) . . . . ?
C6 N2 C9 C8 1.7(3) . . . . ?
C6 N2 C9 C10 -176.2(3) . . . . ?
C6 N2 B1 F1 118.0(3) . . . . ?
C6 N2 B1 F2 -121.2(3) . . . . ?
C6 N2 B1 N1 -1.0(4) . . . . ?
C6 C5 C14 C18 -97.7(4) . . . . ?
C6 C5 C14 C15 84.7(4) . . . . ?
C5 C4 C3 C2 179.5(3) . . . . ?
C5 C4 C3 C12 -0.7(6) . . . . ?
C5 C6 C7 C8 179.8(3) . . . . ?
C5 C6 C7 C11 -2.2(6) . . . . ?
C5 C14 C18 C17 -175.1(3) . . . . ?
C5 C14 C15 C16 175.2(3) . . . . ?
C7 C8 C9 N2 -2.0(4) . . . . ?
C7 C8 C9 C10 175.7(3) . . . . ?
C7 C6 C5 C4 -177.2(3) . . . . ?
C7 C6 C5 C14 4.7(5) . . . . ?
C14 C18 C17 N3 0.2(7) . . . . ?
C14 C15 C16 N3 -0.1(6) . . . . ?
C1 N1 C4 C5 -179.5(3) . . . . ?
C1 N1 C4 C3 0.1(3) . . . . ?
C1 N1 B1 F1 59.4(4) . . . . ?
C1 N1 B1 F2 -61.2(4) . . . . ?
C1 N1 B1 N2 178.6(3) . . . . ?
C3 C4 C5 C6 -179.0(3) . . . . ?
C3 C4 C5 C14 -0.9(5) . . . . ?
C18 C14 C15 C16 -2.5(5) . . . . ?
C15 C14 C18 C17 2.5(5) . . . . ?
C13 C1 C2 C3 179.6(3) . . . . ?
B1 N1 C4 C5 -4.7(4) . . . . ?
B1 N1 C4 C3 174.9(3) . . . . ?
B1 N1 C1 C2 -174.8(3) . . . . ?
B1 N1 C1 C13 5.6(5) . . . . ?
B1 N2 C9 C8 -176.7(3) . . . . ?
B1 N2 C9 C10 5.4(5) . . . . ?
B1 N2 C6 C5 -2.6(4) . . . . ?
B1 N2 C6 C7 177.6(3) . . . . ?
C12 C3 C2 C1 -179.8(3) . . . . ?
C16 N3 C17 C18 -2.7(7) . . . . ?
C17 N3 C16 C15 2.7(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
