# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_21gtu95_bc_bt_33_0m
_database_code_depnum_ccdc_archive 'CCDC 2108981'
loop_
_audit_author_name
_audit_author_address
'Yunus Zorlu'
;Gebze Technical University
Turkey
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-09-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 B F2 I N2'
_chemical_formula_sum            'C19 H18 B F2 I N2'
_chemical_formula_weight         450.06
_chemical_absolute_configuration unk
_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           20
_space_group_name_H-M_alt        'C 2 2 21'
_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'

_cell_length_a                   12.8973(11)
_cell_length_b                   13.3290(11)
_cell_length_c                   10.5740(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1817.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3872
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.92
_shelx_estimated_absorpt_T_max   0.865
_shelx_estimated_absorpt_T_min   0.729
_exptl_absorpt_coefficient_mu    1.784
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1063 before and 0.0513 after correction.
The Ratio of minimum to maximum transmission is 0.8506.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -3.00 1.00 0.0670
1.00 -3.00 -2.00 0.0680
0.00 -1.00 0.00 0.0680
-1.00 -3.00 -2.00 0.0810
-1.00 -1.00 -3.00 0.0930
-1.00 -3.00 0.00 0.0630
2.00 3.00 3.00 0.1020
1.00 2.00 1.00 0.1030
-3.00 -2.00 -2.00 0.0740
3.00 3.00 1.00 0.0840
-3.00 0.00 -1.00 0.0620
3.00 0.00 1.00 0.0410
-1.00 0.00 0.00 0.0350
1.00 0.00 0.00 0.0280
-1.00 3.00 -1.00 0.0550
-3.00 0.00 2.00 0.0420
1.00 -3.00 1.00 0.0590
3.00 0.00 -2.00 0.0340

_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.084
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_av_unetI/netI     0.0506
_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       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6835
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.197
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1464
_reflns_number_total             1609
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 587 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1609
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.016
_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)+(0.0310P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0680
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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 0.5000 0.05932(2) 0.2500 0.0594(2) Uani 1 2 d S T P . .
F1 F 0.4568(2) 0.8225(2) 0.3431(3) 0.0541(8) Uani 1 1 d . . . . .
N1 N 0.5848(3) 0.6933(3) 0.3080(3) 0.0375(9) Uani 1 1 d . . . . .
C1 C 0.6745(4) 0.7219(3) 0.3633(4) 0.0442(11) Uani 1 1 d . . . . .
C2 C 0.7323(4) 0.6352(4) 0.3935(5) 0.0484(12) Uani 1 1 d . . . . .
H2 H 0.7967 0.6340 0.4331 0.058 Uiso 1 1 calc R U . . .
C3 C 0.6771(4) 0.5533(3) 0.3543(4) 0.0443(11) Uani 1 1 d . . . . .
H3 H 0.6973 0.4865 0.3614 0.053 Uiso 1 1 calc R U . . .
C4 C 0.5836(3) 0.5887(3) 0.3011(4) 0.0338(10) Uani 1 1 d . . . . .
C5 C 0.5000 0.5361(4) 0.2500 0.0347(11) Uani 1 2 d S T P . .
C6 C 0.5000 0.4249(4) 0.2500 0.0353(11) Uani 1 2 d S T P . .
C7 C 0.5080(5) 0.3716(3) 0.3623(4) 0.0413(10) Uani 1 1 d . . . . .
H7 H 0.5150 0.4061 0.4382 0.050 Uiso 1 1 calc R U . . .
C8 C 0.5056(6) 0.2677(3) 0.3628(4) 0.0459(10) Uani 1 1 d . . . . .
H8 H 0.5078 0.2328 0.4389 0.055 Uiso 1 1 calc R U . . .
C9 C 0.5000 0.2163(4) 0.2500 0.0397(12) Uani 1 2 d S T P . .
C10 C 0.7051(5) 0.8290(4) 0.3857(7) 0.0696(17) Uani 1 1 d . . . . .
H10A H 0.6443 0.8712 0.3768 0.084 Uiso 1 1 calc R U . . .
H10B H 0.7546 0.8490 0.3215 0.084 Uiso 1 1 calc R U . . .
C11 C 0.7521(5) 0.8461(5) 0.5145(7) 0.0754(19) Uani 1 1 d . . . . .
H11A H 0.8159 0.8095 0.5211 0.113 Uiso 1 1 calc R U . . .
H11B H 0.7048 0.8234 0.5785 0.113 Uiso 1 1 calc R U . . .
H11C H 0.7654 0.9164 0.5258 0.113 Uiso 1 1 calc R U . . .
B1 B 0.5000 0.7628(4) 0.2500 0.0394(13) Uani 1 2 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 C9 2.093(5) . ?
F1 B1 1.383(4) . ?
N1 C1 1.351(6) . ?
N1 C4 1.396(6) . ?
N1 B1 1.559(5) . ?
C1 C2 1.412(7) . ?
C1 C10 1.499(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.411(6) . ?
C4 C5 1.396(5) . ?
C5 C4 1.396(5) 3_655 ?
C5 C6 1.481(7) . ?
C6 C7 1.387(5) . ?
C6 C7 1.387(5) 3_655 ?
C7 H7 0.9300 . ?
C7 C8 1.386(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(5) . ?
C9 C8 1.377(5) 3_655 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.508(10) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
B1 F1 1.383(4) 3_655 ?
B1 N1 1.559(5) 3_655 ?

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 108.3(4) . . ?
C1 N1 B1 127.1(4) . . ?
C4 N1 B1 124.4(4) . . ?
N1 C1 C2 108.6(4) . . ?
N1 C1 C10 124.2(5) . . ?
C2 C1 C10 127.2(5) . . ?
C1 C2 H2 126.0 . . ?
C3 C2 C1 108.0(4) . . ?
C3 C2 H2 126.0 . . ?
C2 C3 H3 126.3 . . ?
C2 C3 C4 107.4(4) . . ?
C4 C3 H3 126.3 . . ?
N1 C4 C3 107.7(4) . . ?
C5 C4 N1 122.1(4) . . ?
C5 C4 C3 130.2(4) . . ?
C4 C5 C4 119.6(5) 3_655 . ?
C4 C5 C6 120.2(3) 3_655 . ?
C4 C5 C6 120.2(3) . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 C5 120.8(2) 3_655 . ?
C7 C6 C7 118.4(5) 3_655 . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.9(4) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.7(4) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 I1 119.8(2) 3_655 . ?
C8 C9 I1 119.8(2) . . ?
C8 C9 C8 120.4(5) 3_655 . ?
C1 C10 H10A 108.9 . . ?
C1 C10 H10B 108.9 . . ?
C1 C10 C11 113.2(5) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
F1 B1 F1 109.7(4) . 3_655 ?
F1 B1 N1 110.15(18) . . ?
F1 B1 N1 109.84(18) 3_655 . ?
F1 B1 N1 109.84(18) . 3_655 ?
F1 B1 N1 110.15(18) 3_655 3_655 ?
N1 B1 N1 107.2(4) 3_655 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.8(6) . . . . ?
N1 C1 C10 C11 137.1(5) . . . . ?
N1 C4 C5 C4 2.8(3) . . . 3_655 ?
N1 C4 C5 C6 -177.2(3) . . . . ?
C1 N1 C4 C3 -0.2(5) . . . . ?
C1 N1 C4 C5 179.1(4) . . . . ?
C1 N1 B1 F1 -63.6(5) . . . . ?
C1 N1 B1 F1 57.4(5) . . . 3_655 ?
C1 N1 B1 N1 177.0(5) . . . 3_655 ?
C1 C2 C3 C4 -0.9(6) . . . . ?
C2 C1 C10 C11 -43.7(9) . . . . ?
C2 C3 C4 N1 0.7(5) . . . . ?
C2 C3 C4 C5 -178.6(4) . . . . ?
C3 C4 C5 C4 -178.0(5) . . . 3_655 ?
C3 C4 C5 C6 2.0(5) . . . . ?
C4 N1 C1 C2 -0.3(5) . . . . ?
C4 N1 C1 C10 179.1(5) . . . . ?
C4 N1 B1 F1 122.2(4) . . . . ?
C4 N1 B1 F1 -116.8(4) . . . 3_655 ?
C4 N1 B1 N1 2.8(3) . . . 3_655 ?
C4 C5 C6 C7 58.4(4) 3_655 . . 3_655 ?
C4 C5 C6 C7 -121.6(4) 3_655 . . . ?
C4 C5 C6 C7 58.4(4) . . . . ?
C4 C5 C6 C7 -121.6(4) . . . 3_655 ?
C5 C6 C7 C8 178.5(6) . . . . ?
C6 C7 C8 C9 3.0(12) . . . . ?
C7 C6 C7 C8 -1.5(6) 3_655 . . . ?
C7 C8 C9 I1 178.5(6) . . . . ?
C7 C8 C9 C8 -1.5(6) . . . 3_655 ?
C10 C1 C2 C3 -178.6(5) . . . . ?
B1 N1 C1 C2 -175.3(3) . . . . ?
B1 N1 C1 C10 4.1(7) . . . . ?
B1 N1 C4 C3 174.9(3) . . . . ?
B1 N1 C4 C5 -5.7(5) . . . . ?

_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_18gtu360_bc_bt_38_0ma
_database_code_depnum_ccdc_archive 'CCDC 2108984'
loop_
_audit_author_name
_audit_author_address
'Yunus Zorlu'
;Gebze Technical University
Turkey
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-09-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 B F2 I2 N2'
_chemical_formula_sum            'C19 H17 B F2 I2 N2'
_chemical_formula_weight         575.96
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   36.279(7)
_cell_length_b                   6.3131(10)
_cell_length_c                   17.888(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.391(13)
_cell_angle_gamma                90
_cell_volume                     3968.5(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1975
_cell_measurement_temperature    296
_cell_measurement_theta_max      19.74
_cell_measurement_theta_min      2.86
_shelx_estimated_absorpt_T_max   0.701
_shelx_estimated_absorpt_T_min   0.479
_exptl_absorpt_coefficient_mu    3.193
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1377 before and 0.0732 after correction.
The Ratio of minimum to maximum transmission is 0.6962.
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    1.928
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0900
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3436
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.051
_diffrn_reflns_theta_max         25.051
_diffrn_reflns_theta_min         1.159
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II QUAZAR'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1995
_reflns_number_total             3436
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.131
_refine_diff_density_min         -1.730
_refine_diff_density_rms         0.194
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3436
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0556
_refine_ls_restrained_S_all      1.036
_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)+(0.0232P)²+30.6496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1267
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.533(3)
 0.467(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Rigid body (RIGU) restrains
 C10, C11, C12, C13, C14, C15
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N2, C6, C7, C8, C9
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
4.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_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 0.61924(3) 0.94171(14) 0.73891(6) 0.0503(3) Uani 1 1 d . . . . .
I2 I 0.62102(3) -0.43501(14) 0.37799(6) 0.0517(3) Uani 1 1 d . . . . .
F1 F 0.54870(19) 0.3485(11) 0.4697(4) 0.046(2) Uani 1 1 d . . . . .
F2 F 0.54843(19) 0.1552(11) 0.5754(4) 0.0432(19) Uani 1 1 d . . . . .
N1 N 0.5973(3) 0.4134(16) 0.5863(6) 0.030(2) Uani 1 1 d . . . . .
N2 N 0.5974(3) 0.0831(17) 0.5112(7) 0.037(3) Uani 1 1 d . U . . .
C1 C 0.5860(4) 0.5823(18) 0.6226(7) 0.034(3) Uani 1 1 d . . . . .
C2 C 0.6189(4) 0.681(2) 0.6688(7) 0.039(3) Uani 1 1 d . . . . .
C3 C 0.6508(4) 0.572(2) 0.6593(8) 0.040(3) Uani 1 1 d . . . . .
H3 H 0.6760 0.6021 0.6836 0.048 Uiso 1 1 calc R U . . .
C4 C 0.6376(3) 0.409(2) 0.6061(8) 0.040(3) Uani 1 1 d . . . . .
C5 C 0.6565(3) 0.252(2) 0.5781(9) 0.039(3) Uani 1 1 d . . . . .
C6 C 0.6383(3) 0.092(2) 0.5304(8) 0.038(3) Uani 1 1 d . U . . .
C7 C 0.6505(4) -0.0725(19) 0.4916(8) 0.038(3) Uani 1 1 d . U . . .
H7 H 0.6758 -0.1063 0.4947 0.046 Uiso 1 1 calc R U . . .
C8 C 0.6202(3) -0.176(2) 0.4489(7) 0.031(2) Uani 1 1 d . U . . .
C9 C 0.5876(3) -0.0813(18) 0.4615(7) 0.026(2) Uani 1 1 d . U . . .
C10 C 0.6984(3) 0.250(3) 0.5999(11) 0.059(3) Uani 1 1 d . U . . .
C11 C 0.7209(5) 0.413(3) 0.5834(11) 0.083(5) Uani 1 1 d . U . . .
H11 H 0.7093 0.5291 0.5547 0.099 Uiso 1 1 calc R U . . .
C12 C 0.7613(5) 0.407(3) 0.6095(14) 0.113(7) Uani 1 1 d . U . . .
H12 H 0.7766 0.5214 0.6045 0.136 Uiso 1 1 calc R U . . .
C13 C 0.7761(4) 0.218(3) 0.6428(13) 0.092(4) Uani 1 1 d . U . . .
H13 H 0.8023 0.1970 0.6523 0.111 Uiso 1 1 calc R U . . .
C14 C 0.7554(4) 0.066(3) 0.6619(12) 0.098(6) Uani 1 1 d . U . . .
H14 H 0.7669 -0.0482 0.6918 0.118 Uiso 1 1 calc R U . . .
C15 C 0.7171(4) 0.077(3) 0.6373(11) 0.088(5) Uani 1 1 d . U . . .
H15 H 0.7027 -0.0375 0.6462 0.105 Uiso 1 1 calc R U . . .
C16 C 0.5461(3) -0.134(2) 0.4260(7) 0.040(3) Uani 1 1 d . . . . .
H16A H 0.5306 -0.0767 0.4582 0.048 Uiso 1 1 calc R U . . .
H16B H 0.5428 -0.2861 0.4235 0.048 Uiso 1 1 calc R U . . .
C17 C 0.5330(3) -0.040(2) 0.3447(10) 0.048(4) Uani 1 1 d . . . . .
H17A H 0.5514 -0.0728 0.3160 0.072 Uiso 1 1 calc R U . . .
H17B H 0.5306 0.1106 0.3481 0.072 Uiso 1 1 calc R U . . .
H17C H 0.5089 -0.1001 0.3191 0.072 Uiso 1 1 calc R U . . .
C18 C 0.5460(3) 0.6297(19) 0.6191(7) 0.031(3) Uani 1 1 d . . . . .
H18A H 0.5304 0.5758 0.5709 0.037 Uiso 1 1 calc R U . . .
H18B H 0.5428 0.7822 0.6190 0.037 Uiso 1 1 calc R U . . .
C19 C 0.5321(4) 0.538(2) 0.6843(10) 0.056(5) Uani 1 1 d . . . . .
H19A H 0.5419 0.3972 0.6950 0.084 Uiso 1 1 calc R U . . .
H19B H 0.5048 0.5338 0.6702 0.084 Uiso 1 1 calc R U . . .
H19C H 0.5406 0.6247 0.7294 0.084 Uiso 1 1 calc R U . . .
B1 B 0.5712(3) 0.252(3) 0.5329(11) 0.032(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C2 2.069(14) . ?
I2 C8 2.075(13) . ?
F1 B1 1.365(17) . ?
F2 B1 1.394(17) . ?
N1 C1 1.364(15) . ?
N1 C4 1.414(15) . ?
N1 B1 1.549(17) . ?
N2 C6 1.437(15) . ?
N2 C9 1.355(15) . ?
N2 B1 1.540(18) . ?
C1 C2 1.415(16) . ?
C1 C18 1.468(17) . ?
C2 C3 1.390(16) . ?
C3 H3 0.9300 . ?
C3 C4 1.406(17) . ?
C4 C5 1.370(17) . ?
C5 C6 1.378(17) . ?
C5 C10 1.471(13) . ?
C6 C7 1.383(18) . ?
C7 H7 0.9300 . ?
C7 C8 1.344(16) . ?
C8 C9 1.390(15) . ?
C9 C16 1.518(15) . ?
C10 C11 1.39(2) . ?
C10 C15 1.37(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.42(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.38(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.32(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.350(18) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.53(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.50(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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 108.1(11) . . ?
C1 N1 B1 126.7(10) . . ?
C4 N1 B1 125.2(11) . . ?
C6 N2 B1 125.2(11) . . ?
C9 N2 C6 105.9(11) . . ?
C9 N2 B1 128.2(10) . . ?
N1 C1 C2 108.2(11) . . ?
N1 C1 C18 123.4(11) . . ?
C2 C1 C18 128.0(11) . . ?
C1 C2 I1 125.5(9) . . ?
C3 C2 I1 125.9(10) . . ?
C3 C2 C1 108.6(12) . . ?
C2 C3 H3 126.6 . . ?
C2 C3 C4 106.8(11) . . ?
C4 C3 H3 126.6 . . ?
C3 C4 N1 108.2(12) . . ?
C5 C4 N1 120.2(12) . . ?
C5 C4 C3 131.4(12) . . ?
C4 C5 C6 123.2(9) . . ?
C4 C5 C10 119.1(14) . . ?
C6 C5 C10 117.7(14) . . ?
C5 C6 N2 119.0(12) . . ?
C5 C6 C7 134.0(12) . . ?
C7 C6 N2 106.9(12) . . ?
C6 C7 H7 125.4 . . ?
C8 C7 C6 109.3(12) . . ?
C8 C7 H7 125.4 . . ?
C7 C8 I2 126.6(10) . . ?
C7 C8 C9 107.9(11) . . ?
C9 C8 I2 125.5(9) . . ?
N2 C9 C8 110.0(10) . . ?
N2 C9 C16 120.8(11) . . ?
C8 C9 C16 129.2(12) . . ?
C11 C10 C5 124.1(17) . . ?
C15 C10 C5 119.2(18) . . ?
C15 C10 C11 116.6(11) . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.2(18) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 122.4 . . ?
C13 C12 C11 115.3(17) . . ?
C13 C12 H12 122.4 . . ?
C12 C13 H13 118.2 . . ?
C14 C13 C12 123.7(14) . . ?
C14 C13 H13 118.2 . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.9(19) . . ?
C15 C14 H14 120.6 . . ?
C10 C15 H15 118.4 . . ?
C14 C15 C10 123.3(19) . . ?
C14 C15 H15 118.4 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
C9 C16 C17 110.8(11) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 C18 H18A 108.7 . . ?
C1 C18 H18B 108.7 . . ?
C1 C18 C19 114.3(11) . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
F1 B1 F2 109.5(8) . . ?
F1 B1 N1 111.4(13) . . ?
F1 B1 N2 112.3(13) . . ?
F2 B1 N1 107.9(13) . . ?
F2 B1 N2 108.8(13) . . ?
N2 B1 N1 106.8(7) . . ?

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 -179.2(10) . . . . ?
I2 C8 C9 N2 179.7(9) . . . . ?
I2 C8 C9 C16 -2.8(18) . . . . ?
N1 C1 C2 I1 -178.7(9) . . . . ?
N1 C1 C2 C3 1.1(15) . . . . ?
N1 C1 C18 C19 93.2(16) . . . . ?
N1 C4 C5 C6 0(3) . . . . ?
N1 C4 C5 C10 -179.9(15) . . . . ?
N2 C6 C7 C8 1.7(17) . . . . ?
N2 C9 C16 C17 98.3(14) . . . . ?
C1 N1 C4 C3 3.4(16) . . . . ?
C1 N1 C4 C5 179.0(12) . . . . ?
C1 N1 B1 F1 61.0(18) . . . . ?
C1 N1 B1 F2 -59.2(17) . . . . ?
C1 N1 B1 N2 -176.0(10) . . . . ?
C1 C2 C3 C4 1.0(15) . . . . ?
C2 C1 C18 C19 -78.8(17) . . . . ?
C2 C3 C4 N1 -2.6(16) . . . . ?
C2 C3 C4 C5 -177.6(16) . . . . ?
C3 C4 C5 C6 174.3(13) . . . . ?
C3 C4 C5 C10 -5(3) . . . . ?
C4 N1 C1 C2 -2.7(15) . . . . ?
C4 N1 C1 C18 -176.1(12) . . . . ?
C4 N1 B1 F1 -119.6(13) . . . . ?
C4 N1 B1 F2 120.2(13) . . . . ?
C4 N1 B1 N2 3(2) . . . . ?
C4 C5 C6 N2 -3(3) . . . . ?
C4 C5 C6 C7 175.3(14) . . . . ?
C4 C5 C10 C11 -60(3) . . . . ?
C4 C5 C10 C15 121.1(19) . . . . ?
C5 C6 C7 C8 -176.4(16) . . . . ?
C5 C10 C11 C12 176.8(19) . . . . ?
C5 C10 C15 C14 -177.5(19) . . . . ?
C6 N2 C9 C8 0.2(15) . . . . ?
C6 N2 C9 C16 -177.6(11) . . . . ?
C6 N2 B1 F1 116.0(14) . . . . ?
C6 N2 B1 F2 -122.6(14) . . . . ?
C6 N2 B1 N1 -6(2) . . . . ?
C6 C5 C10 C11 120(2) . . . . ?
C6 C5 C10 C15 -59(2) . . . . ?
C6 C7 C8 I2 179.6(10) . . . . ?
C6 C7 C8 C9 -1.6(15) . . . . ?
C7 C8 C9 N2 0.8(14) . . . . ?
C7 C8 C9 C16 178.4(13) . . . . ?
C8 C9 C16 C17 -79.0(16) . . . . ?
C9 N2 C6 C5 177.3(12) . . . . ?
C9 N2 C6 C7 -1.2(16) . . . . ?
C9 N2 B1 F1 -52.7(18) . . . . ?
C9 N2 B1 F2 68.7(18) . . . . ?
C9 N2 B1 N1 -175.1(10) . . . . ?
C10 C5 C6 N2 177.0(15) . . . . ?
C10 C5 C6 C7 -5(3) . . . . ?
C10 C11 C12 C13 8(3) . . . . ?
C11 C10 C15 C14 4(3) . . . . ?
C11 C12 C13 C14 -11(4) . . . . ?
C12 C13 C14 C15 11(4) . . . . ?
C13 C14 C15 C10 -7(3) . . . . ?
C15 C10 C11 C12 -5(3) . . . . ?
C18 C1 C2 I1 -6(2) . . . . ?
C18 C1 C2 C3 174.1(13) . . . . ?
B1 N1 C1 C2 176.7(13) . . . . ?
B1 N1 C1 C18 3(2) . . . . ?
B1 N1 C4 C3 -176.1(12) . . . . ?
B1 N1 C4 C5 0(2) . . . . ?
B1 N2 C6 C5 6(2) . . . . ?
B1 N2 C6 C7 -172.0(13) . . . . ?
B1 N2 C9 C8 170.6(13) . . . . ?
B1 N2 C9 C16 -7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.533(3)
2 0.467(3)

####################################################################### 
# 
# 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_21gtu80_bc_bt_37_0m
_database_code_depnum_ccdc_archive 'CCDC 2108982'
loop_
_audit_author_name
_audit_author_address
'Yunus Zorlu'
;Gebze Technical University
Turkey
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-09-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 B F2 I N2'
_chemical_formula_sum            'C19 H18 B F2 I N2'
_chemical_formula_weight         450.06
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.649(2)
_cell_length_b                   10.479(4)
_cell_length_c                   14.000(5)
_cell_angle_alpha                106.646(8)
_cell_angle_beta                 96.659(8)
_cell_angle_gamma                97.135(8)
_cell_volume                     915.4(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2124
_cell_measurement_temperature    298
_cell_measurement_theta_max      19.61
_cell_measurement_theta_min      2.92
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.814
_exptl_absorpt_coefficient_mu    1.771
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0857 before and 0.0565 after correction.
The Ratio of minimum to maximum transmission is 0.7571.
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    1.633
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 -2.00 -3.00 0.0210
0.00 2.00 3.00 0.0070
-3.00 1.00 2.00 0.0590
2.00 3.00 2.00 0.0250
3.00 -2.00 -3.00 0.0530
0.00 -3.00 -2.00 0.0230
0.00 -3.00 -1.00 0.0260
0.00 -2.00 1.00 0.0320
0.00 2.00 -1.00 0.0100
0.00 2.00 -3.00 0.0100

_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1084
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9330
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.036
_diffrn_reflns_theta_max         25.036
_diffrn_reflns_theta_min         1.538
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6236
_reflns_number_total             9330
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.029
_refine_diff_density_min         -1.081
_refine_diff_density_rms         0.157
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         9330
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0729
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1115P)²+1.5317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1908
_refine_ls_wR_factor_ref         0.2136
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.842(4)
 0.158(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Rigid body (RIGU) restrains
 I1, C1, C2, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C10, C11, C12, C13, C14, C15
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
4.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_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 -0.10350(13) 0.06610(10) 0.69738(8) 0.0529(4) Uani 1 1 d . U . . .
F1 F 0.7452(11) 0.3745(9) 0.8909(6) 0.066(2) Uani 1 1 d . . . . .
F2 F 0.6007(11) 0.5440(8) 0.8626(6) 0.064(2) Uani 1 1 d . . . . .
N1 N 0.4717(14) 0.3218(10) 0.7508(7) 0.037(2) Uani 1 1 d . . . . .
N2 N 0.8171(14) 0.4424(9) 0.7474(7) 0.034(2) Uani 1 1 d . . . . .
C1 C 0.3060(17) 0.2657(12) 0.7819(9) 0.038(3) Uani 1 1 d . U . . .
C2 C 0.1765(16) 0.1858(11) 0.6962(9) 0.033(2) Uani 1 1 d . U . . .
C3 C 0.2538(17) 0.1871(12) 0.6111(10) 0.038(3) Uani 1 1 d . U . . .
H3 H 0.1952 0.1386 0.5450 0.046 Uiso 1 1 calc R U . . .
C4 C 0.4411(16) 0.2769(11) 0.6435(8) 0.030(3) Uani 1 1 d . . . . .
C5 C 0.5935(16) 0.3125(12) 0.5918(8) 0.033(3) Uani 1 1 d . . . . .
C6 C 0.7790(17) 0.3905(12) 0.6419(9) 0.035(3) Uani 1 1 d . . . . .
C7 C 0.9526(18) 0.4365(13) 0.6050(10) 0.044(3) Uani 1 1 d . . . . .
H7 H 0.9694 0.4168 0.5375 0.053 Uiso 1 1 calc R U . . .
C8 C 1.0933(17) 0.5161(13) 0.6867(10) 0.045(3) Uani 1 1 d . . . . .
H8 H 1.2220 0.5607 0.6848 0.053 Uiso 1 1 calc R U . . .
C9 C 1.0056(17) 0.5175(13) 0.7746(9) 0.040(3) Uani 1 1 d . . . . .
C10 C 0.5520(17) 0.2686(12) 0.4805(9) 0.036(3) Uani 1 1 d . U . . .
C11 C 0.657(2) 0.1762(15) 0.4233(10) 0.057(4) Uani 1 1 d . U . . .
H11 H 0.7558 0.1402 0.4551 0.069 Uiso 1 1 calc R U . . .
C12 C 0.614(2) 0.1366(15) 0.3171(11) 0.061(4) Uani 1 1 d . U . . .
H12 H 0.6828 0.0736 0.2788 0.073 Uiso 1 1 calc R U . . .
C13 C 0.473(2) 0.1899(15) 0.2717(11) 0.055(4) Uani 1 1 d . U . . .
H13 H 0.4498 0.1665 0.2016 0.066 Uiso 1 1 calc R U . . .
C14 C 0.365(2) 0.2769(14) 0.3257(10) 0.051(3) Uani 1 1 d . U . . .
H14 H 0.2654 0.3110 0.2928 0.062 Uiso 1 1 calc R U . . .
C15 C 0.4027(19) 0.3157(13) 0.4303(9) 0.045(3) Uani 1 1 d . U . . .
H15 H 0.3255 0.3745 0.4669 0.054 Uiso 1 1 calc R U . . .
C16 C 1.0930(19) 0.5987(14) 0.8792(10) 0.052(4) Uani 1 1 d . . . . .
H16A H 1.2364 0.5900 0.8920 0.062 Uiso 1 1 calc R U . . .
H16B H 1.0220 0.5633 0.9252 0.062 Uiso 1 1 calc R U . . .
C17 C 1.077(3) 0.7485(14) 0.9009(11) 0.072(5) Uani 1 1 d . . . . .
H17A H 1.1284 0.7810 0.8494 0.107 Uiso 1 1 calc R U . . .
H17B H 1.1563 0.7989 0.9654 0.107 Uiso 1 1 calc R U . . .
H17C H 0.9358 0.7597 0.9014 0.107 Uiso 1 1 calc R U . . .
C18 C 0.288(2) 0.2851(15) 0.8910(10) 0.053(4) Uani 1 1 d . . . . .
H18A H 0.3677 0.3715 0.9316 0.064 Uiso 1 1 calc R U . . .
H18B H 0.1454 0.2878 0.8993 0.064 Uiso 1 1 calc R U . . .
C19 C 0.358(2) 0.1777(16) 0.9286(11) 0.069(4) Uani 1 1 d . . . . .
H19A H 0.2562 0.0977 0.9039 0.104 Uiso 1 1 calc R U . . .
H19B H 0.3799 0.2073 1.0011 0.104 Uiso 1 1 calc R U . . .
H19C H 0.4847 0.1584 0.9054 0.104 Uiso 1 1 calc R U . . .
B1 B 0.660(2) 0.4229(16) 0.8172(12) 0.044(4) 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
I1 C2 2.116(12) . ?
F1 B1 1.370(18) . ?
F2 B1 1.376(16) . ?
N1 C1 1.359(15) . ?
N1 C4 1.420(14) . ?
N1 B1 1.547(17) . ?
N2 C6 1.400(14) . ?
N2 C9 1.344(14) . ?
N2 B1 1.543(17) . ?
C1 C2 1.374(16) . ?
C1 C18 1.503(17) . ?
C2 C3 1.353(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.405(16) . ?
C4 C5 1.386(15) . ?
C5 C6 1.379(16) . ?
C5 C10 1.474(16) . ?
C6 C7 1.406(16) . ?
C7 H7 0.9300 . ?
C7 C8 1.375(17) . ?
C8 H8 0.9300 . ?
C8 C9 1.419(17) . ?
C9 C16 1.474(17) . ?
C10 C11 1.383(17) . ?
C10 C15 1.373(17) . ?
C11 H11 0.9300 . ?
C11 C12 1.408(18) . ?
C12 H12 0.9300 . ?
C12 C13 1.335(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.347(18) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(17) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.531(19) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.48(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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 108.4(10) . . ?
C1 N1 B1 127.6(11) . . ?
C4 N1 B1 124.0(10) . . ?
C6 N2 B1 124.7(10) . . ?
C9 N2 C6 107.9(10) . . ?
C9 N2 B1 127.3(10) . . ?
N1 C1 C2 106.6(10) . . ?
N1 C1 C18 123.7(11) . . ?
C2 C1 C18 129.6(11) . . ?
C1 C2 I1 123.9(9) . . ?
C3 C2 I1 123.9(9) . . ?
C3 C2 C1 112.2(11) . . ?
C2 C3 H3 127.2 . . ?
C2 C3 C4 105.7(11) . . ?
C4 C3 H3 127.2 . . ?
C3 C4 N1 107.1(10) . . ?
C5 C4 N1 120.4(10) . . ?
C5 C4 C3 132.1(11) . . ?
C4 C5 C10 118.6(10) . . ?
C6 C5 C4 121.6(10) . . ?
C6 C5 C10 119.7(10) . . ?
N2 C6 C7 108.0(10) . . ?
C5 C6 N2 121.1(10) . . ?
C5 C6 C7 130.9(11) . . ?
C6 C7 H7 126.2 . . ?
C8 C7 C6 107.5(11) . . ?
C8 C7 H7 126.2 . . ?
C7 C8 H8 126.4 . . ?
C7 C8 C9 107.3(11) . . ?
C9 C8 H8 126.4 . . ?
N2 C9 C8 109.3(10) . . ?
N2 C9 C16 123.9(11) . . ?
C8 C9 C16 126.5(11) . . ?
C11 C10 C5 121.6(11) . . ?
C15 C10 C5 120.5(11) . . ?
C15 C10 C11 117.8(12) . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(13) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(13) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.0(14) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(13) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.9(12) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C9 C16 H16A 109.0 . . ?
C9 C16 H16B 109.0 . . ?
C9 C16 C17 113.0(11) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 C18 H18A 108.9 . . ?
C1 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 C1 113.3(11) . . ?
C19 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
F1 B1 F2 108.6(12) . . ?
F1 B1 N1 110.6(12) . . ?
F1 B1 N2 110.4(10) . . ?
F2 B1 N1 109.6(10) . . ?
F2 B1 N2 110.2(12) . . ?
N2 B1 N1 107.5(11) . . ?

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 -178.9(7) . . . . ?
N1 C1 C2 I1 177.5(7) . . . . ?
N1 C1 C2 C3 0.8(14) . . . . ?
N1 C1 C18 C19 -93.3(16) . . . . ?
N1 C4 C5 C6 0.8(17) . . . . ?
N1 C4 C5 C10 -177.4(10) . . . . ?
N2 C6 C7 C8 -0.5(14) . . . . ?
N2 C9 C16 C17 -99.3(15) . . . . ?
C1 N1 C4 C3 -2.3(13) . . . . ?
C1 N1 C4 C5 -176.0(10) . . . . ?
C1 N1 B1 F1 52.6(16) . . . . ?
C1 N1 B1 F2 -67.1(17) . . . . ?
C1 N1 B1 N2 173.2(11) . . . . ?
C1 C2 C3 C4 -2.2(13) . . . . ?
C2 C1 C18 C19 81.9(17) . . . . ?
C2 C3 C4 N1 2.7(13) . . . . ?
C2 C3 C4 C5 175.4(12) . . . . ?
C3 C4 C5 C6 -171.1(12) . . . . ?
C3 C4 C5 C10 10.7(19) . . . . ?
C4 N1 C1 C2 0.9(13) . . . . ?
C4 N1 C1 C18 177.1(11) . . . . ?
C4 N1 B1 F1 -130.4(12) . . . . ?
C4 N1 B1 F2 109.9(13) . . . . ?
C4 N1 B1 N2 -9.9(16) . . . . ?
C4 C5 C6 N2 -3.1(18) . . . . ?
C4 C5 C6 C7 179.3(12) . . . . ?
C4 C5 C10 C11 -113.4(14) . . . . ?
C4 C5 C10 C15 64.7(16) . . . . ?
C5 C6 C7 C8 177.3(13) . . . . ?
C5 C10 C11 C12 -179.9(13) . . . . ?
C5 C10 C15 C14 178.8(12) . . . . ?
C6 N2 C9 C8 0.3(14) . . . . ?
C6 N2 C9 C16 174.3(11) . . . . ?
C6 N2 B1 F1 128.3(12) . . . . ?
C6 N2 B1 F2 -111.8(12) . . . . ?
C6 N2 B1 N1 7.6(16) . . . . ?
C6 C5 C10 C11 68.4(17) . . . . ?
C6 C5 C10 C15 -113.6(13) . . . . ?
C6 C7 C8 C9 0.6(14) . . . . ?
C7 C8 C9 N2 -0.6(14) . . . . ?
C7 C8 C9 C16 -174.4(12) . . . . ?
C8 C9 C16 C17 73.7(17) . . . . ?
C9 N2 C6 C5 -177.9(11) . . . . ?
C9 N2 C6 C7 0.1(13) . . . . ?
C9 N2 B1 F1 -56.4(17) . . . . ?
C9 N2 B1 F2 63.6(17) . . . . ?
C9 N2 B1 N1 -177.1(11) . . . . ?
C10 C5 C6 N2 175.1(10) . . . . ?
C10 C5 C6 C7 -2(2) . . . . ?
C10 C11 C12 C13 1(2) . . . . ?
C11 C10 C15 C14 -3.1(19) . . . . ?
C11 C12 C13 C14 -3(2) . . . . ?
C12 C13 C14 C15 2(2) . . . . ?
C13 C14 C15 C10 1(2) . . . . ?
C15 C10 C11 C12 2(2) . . . . ?
C18 C1 C2 I1 1.6(18) . . . . ?
C18 C1 C2 C3 -175.1(12) . . . . ?
B1 N1 C1 C2 178.3(11) . . . . ?
B1 N1 C1 C18 -5.5(19) . . . . ?
B1 N1 C4 C3 -179.7(11) . . . . ?
B1 N1 C4 C5 6.5(17) . . . . ?
B1 N2 C6 C5 -1.8(18) . . . . ?
B1 N2 C6 C7 176.3(11) . . . . ?
B1 N2 C9 C8 -175.7(11) . . . . ?
B1 N2 C9 C16 -2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.842(4)
2 0.158(4)

####################################################################### 
# 
# 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_18gtu363_bc_bt_35_0ma
_database_code_depnum_ccdc_archive 'CCDC 2108983'
loop_
_audit_author_name
_audit_author_address
'Yunus Zorlu'
;Gebze Technical University
Turkey
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-09-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 B F2 I2 N2'
_chemical_formula_sum            'C19 H17 B F2 I2 N2'
_chemical_formula_weight         575.96
_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                   14.782(6)
_cell_length_b                   10.554(4)
_cell_length_c                   13.415(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.167(7)
_cell_angle_gamma                90
_cell_volume                     1999.6(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1735
_cell_measurement_temperature    298
_cell_measurement_theta_max      22.53
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.865
_shelx_estimated_absorpt_T_min   0.641
_exptl_absorpt_coefficient_mu    3.168
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.913
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1096
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2.00 -4.00 -3.00 0.0490
2.00 3.00 0.00 0.0540
-3.00 1.00 3.00 0.0640
4.00 0.00 -3.00 0.0250
2.00 -4.00 -1.00 0.0470
-2.00 4.00 1.00 0.0500
-3.00 0.00 2.00 0.0370
1.00 -4.00 2.00 0.0490
4.00 0.00 -1.00 0.0230
-4.00 0.00 1.00 0.0150
2.00 -1.00 3.00 0.0570
-3.00 4.00 -3.00 0.0160
-1.00 0.00 -1.00 0.0210

_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.047
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8789
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         1.442
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2454
_reflns_number_total             3510
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.246
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3510
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.023
_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)+(0.0337P)²+3.9160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0974
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_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 0.24161(3) 0.52004(5) 0.96434(3) 0.05628(18) Uani 1 1 d . . . . .
I2 I 0.55039(3) 0.23701(6) 0.48264(4) 0.0645(2) Uani 1 1 d . . . . .
F1 F 0.2521(3) 0.5754(4) 0.2036(3) 0.0518(10) Uani 1 1 d . . . . .
F2 F 0.1676(3) 0.3976(4) 0.1962(3) 0.0571(11) Uani 1 1 d . . . . .
N1 N 0.1472(3) 0.5628(5) 0.3098(4) 0.0377(12) Uani 1 1 d . . . . .
N2 N 0.2955(3) 0.4365(5) 0.3522(4) 0.0340(12) Uani 1 1 d . . . . .
C1 C 0.0675(5) 0.6271(7) 0.2600(5) 0.0484(17) Uani 1 1 d . . . . .
C2 C 0.0253(5) 0.6723(8) 0.3335(6) 0.066(2) Uani 1 1 d . . . . .
H2 H -0.0294 0.7212 0.3195 0.079 Uiso 1 1 calc R U . . .
C3 C 0.0779(5) 0.6325(7) 0.4280(6) 0.057(2) Uani 1 1 d . . . . .
H3 H 0.0648 0.6475 0.4907 0.068 Uiso 1 1 calc R U . . .
C4 C 0.1554(4) 0.5649(6) 0.4164(5) 0.0389(15) Uani 1 1 d . . . . .
C5 C 0.2278(4) 0.5029(6) 0.4879(4) 0.0339(14) Uani 1 1 d . . . . .
C6 C 0.2958(4) 0.4389(6) 0.4564(4) 0.0361(15) Uani 1 1 d . . . . .
C7 C 0.3777(4) 0.3759(6) 0.5140(5) 0.0402(15) Uani 1 1 d . . . . .
H7 H 0.3962 0.3621 0.5856 0.048 Uiso 1 1 calc R U . . .
C8 C 0.4259(4) 0.3380(6) 0.4464(5) 0.0407(15) Uani 1 1 d . . . . .
C9 C 0.3738(4) 0.3766(6) 0.3466(5) 0.0374(15) Uani 1 1 d . . . . .
C10 C 0.2336(4) 0.5058(6) 0.6004(4) 0.0344(14) Uani 1 1 d . . . . .
C11 C 0.2404(4) 0.6210(6) 0.6522(5) 0.0425(16) Uani 1 1 d . . . . .
H11 H 0.2420 0.6958 0.6162 0.051 Uiso 1 1 calc R U . . .
C12 C 0.2449(5) 0.6259(7) 0.7564(5) 0.0471(17) Uani 1 1 d . . . . .
H12 H 0.2511 0.7031 0.7912 0.057 Uiso 1 1 calc R U . . .
C13 C 0.2400(4) 0.5135(6) 0.8081(5) 0.0405(16) Uani 1 1 d . . . . .
C14 C 0.2335(4) 0.3983(6) 0.7571(5) 0.0414(16) Uani 1 1 d . . . . .
H14 H 0.2310 0.3232 0.7924 0.050 Uiso 1 1 calc R U . . .
C15 C 0.2306(4) 0.3960(6) 0.6542(5) 0.0403(15) Uani 1 1 d . . . . .
H15 H 0.2266 0.3186 0.6201 0.048 Uiso 1 1 calc R U . . .
C16 C 0.4001(5) 0.3610(7) 0.2476(5) 0.0493(18) Uani 1 1 d . . . . .
H16A H 0.3434 0.3672 0.1887 0.059 Uiso 1 1 calc R U . . .
H16B H 0.4267 0.2771 0.2465 0.059 Uiso 1 1 calc R U . . .
C17 C 0.4706(6) 0.4585(9) 0.2358(6) 0.073(2) Uani 1 1 d . . . . .
H17A H 0.4819 0.4478 0.1694 0.110 Uiso 1 1 calc R U . . .
H17B H 0.5289 0.4480 0.2905 0.110 Uiso 1 1 calc R U . . .
H17C H 0.4459 0.5418 0.2398 0.110 Uiso 1 1 calc R U . . .
C18 C 0.0332(5) 0.6393(8) 0.1441(5) 0.063(2) Uani 1 1 d . . . . .
H18A H 0.0868 0.6559 0.1184 0.076 Uiso 1 1 calc R U . . .
H18B H 0.0052 0.5595 0.1145 0.076 Uiso 1 1 calc R U . . .
C19 C -0.0380(5) 0.7422(9) 0.1080(7) 0.080(3) Uani 1 1 d . . . . .
H19A H -0.0596 0.7431 0.0331 0.120 Uiso 1 1 calc R U . . .
H19B H -0.0095 0.8223 0.1330 0.120 Uiso 1 1 calc R U . . .
H19C H -0.0907 0.7275 0.1345 0.120 Uiso 1 1 calc R U . . .
B1 B 0.2152(5) 0.4924(7) 0.2604(5) 0.0394(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
I1 C13 2.091(6) . ?
I2 C8 2.057(6) . ?
F1 B1 1.375(8) . ?
F2 B1 1.371(8) . ?
N1 C1 1.353(8) . ?
N1 C4 1.399(7) . ?
N1 B1 1.547(9) . ?
N2 C6 1.397(7) . ?
N2 C9 1.341(7) . ?
N2 B1 1.553(8) . ?
C1 C2 1.396(10) . ?
C1 C18 1.491(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.344(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.397(9) . ?
C4 C5 1.374(8) . ?
C5 C6 1.376(8) . ?
C5 C10 1.486(8) . ?
C6 C7 1.397(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.368(8) . ?
C8 C9 1.394(8) . ?
C9 C16 1.499(8) . ?
C10 C11 1.389(8) . ?
C10 C15 1.373(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.387(9) . ?
C13 C14 1.384(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.368(8) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.506(10) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.490(10) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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 107.2(5) . . ?
C1 N1 B1 127.6(5) . . ?
C4 N1 B1 125.0(5) . . ?
C6 N2 B1 124.3(5) . . ?
C9 N2 C6 108.5(5) . . ?
C9 N2 B1 127.2(5) . . ?
N1 C1 C2 109.2(6) . . ?
N1 C1 C18 122.4(6) . . ?
C2 C1 C18 128.4(6) . . ?
C1 C2 H2 126.1 . . ?
C3 C2 C1 107.8(6) . . ?
C3 C2 H2 126.1 . . ?
C2 C3 H3 125.7 . . ?
C2 C3 C4 108.6(6) . . ?
C4 C3 H3 125.7 . . ?
C3 C4 N1 107.2(5) . . ?
C5 C4 N1 121.4(5) . . ?
C5 C4 C3 131.4(6) . . ?
C4 C5 C6 120.6(6) . . ?
C4 C5 C10 119.9(5) . . ?
C6 C5 C10 119.6(5) . . ?
N2 C6 C7 106.9(5) . . ?
C5 C6 N2 121.9(5) . . ?
C5 C6 C7 131.0(6) . . ?
C6 C7 H7 126.0 . . ?
C8 C7 C6 108.0(6) . . ?
C8 C7 H7 126.0 . . ?
C7 C8 I2 126.9(5) . . ?
C7 C8 C9 107.6(5) . . ?
C9 C8 I2 125.5(5) . . ?
N2 C9 C8 109.0(5) . . ?
N2 C9 C16 123.8(5) . . ?
C8 C9 C16 127.2(6) . . ?
C11 C10 C5 120.0(6) . . ?
C15 C10 C5 121.1(6) . . ?
C15 C10 C11 118.9(6) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.0(6) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.7 . . ?
C11 C12 C13 118.7(6) . . ?
C13 C12 H12 120.7 . . ?
C12 C13 I1 119.1(5) . . ?
C14 C13 I1 120.2(5) . . ?
C14 C13 C12 120.7(6) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.4(6) . . ?
C15 C14 H14 120.3 . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.3(6) . . ?
C14 C15 H15 119.3 . . ?
C9 C16 H16A 109.0 . . ?
C9 C16 H16B 109.0 . . ?
C9 C16 C17 112.8(6) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 C18 H18A 109.0 . . ?
C1 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 C1 113.1(7) . . ?
C19 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
F1 B1 N1 110.2(5) . . ?
F1 B1 N2 110.2(5) . . ?
F2 B1 F1 109.3(5) . . ?
F2 B1 N1 110.0(6) . . ?
F2 B1 N2 110.6(5) . . ?
N1 B1 N2 106.5(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
I1 C13 C14 C15 178.7(5) . . . . ?
I2 C8 C9 N2 178.0(4) . . . . ?
I2 C8 C9 C16 -4.5(10) . . . . ?
N1 C1 C2 C3 -1.7(9) . . . . ?
N1 C1 C18 C19 -163.5(7) . . . . ?
N1 C4 C5 C6 1.4(10) . . . . ?
N1 C4 C5 C10 -179.2(6) . . . . ?
N2 C6 C7 C8 0.7(7) . . . . ?
N2 C9 C16 C17 97.8(8) . . . . ?
C1 N1 C4 C3 0.0(7) . . . . ?
C1 N1 C4 C5 177.4(6) . . . . ?
C1 N1 B1 F1 59.8(9) . . . . ?
C1 N1 B1 F2 -60.8(9) . . . . ?
C1 N1 B1 N2 179.4(6) . . . . ?
C1 C2 C3 C4 1.7(9) . . . . ?
C2 C1 C18 C19 18.9(12) . . . . ?
C2 C3 C4 N1 -1.1(9) . . . . ?
C2 C3 C4 C5 -178.2(7) . . . . ?
C3 C4 C5 C6 178.1(7) . . . . ?
C3 C4 C5 C10 -2.5(11) . . . . ?
C4 N1 C1 C2 1.0(8) . . . . ?
C4 N1 C1 C18 -177.0(6) . . . . ?
C4 N1 B1 F1 -123.9(6) . . . . ?
C4 N1 B1 F2 115.5(6) . . . . ?
C4 N1 B1 N2 -4.4(8) . . . . ?
C4 C5 C6 N2 1.5(9) . . . . ?
C4 C5 C6 C7 176.0(7) . . . . ?
C4 C5 C10 C11 -58.7(8) . . . . ?
C4 C5 C10 C15 120.1(7) . . . . ?
C5 C6 C7 C8 -174.4(7) . . . . ?
C5 C10 C11 C12 179.4(6) . . . . ?
C5 C10 C15 C14 -178.3(5) . . . . ?
C6 N2 C9 C8 0.5(7) . . . . ?
C6 N2 C9 C16 -177.1(6) . . . . ?
C6 N2 B1 F1 126.7(6) . . . . ?
C6 N2 B1 F2 -112.3(6) . . . . ?
C6 N2 B1 N1 7.2(8) . . . . ?
C6 C5 C10 C11 120.7(7) . . . . ?
C6 C5 C10 C15 -60.5(8) . . . . ?
C6 C7 C8 I2 -178.5(5) . . . . ?
C6 C7 C8 C9 -0.4(8) . . . . ?
C7 C8 C9 N2 -0.1(7) . . . . ?
C7 C8 C9 C16 177.4(6) . . . . ?
C8 C9 C16 C17 -79.4(9) . . . . ?
C9 N2 C6 C5 174.9(6) . . . . ?
C9 N2 C6 C7 -0.8(7) . . . . ?
C9 N2 B1 F1 -54.8(8) . . . . ?
C9 N2 B1 F2 66.2(8) . . . . ?
C9 N2 B1 N1 -174.3(6) . . . . ?
C10 C5 C6 N2 -177.9(5) . . . . ?
C10 C5 C6 C7 -3.5(10) . . . . ?
C10 C11 C12 C13 -1.6(10) . . . . ?
C11 C10 C15 C14 0.6(9) . . . . ?
C11 C12 C13 I1 -177.7(5) . . . . ?
C11 C12 C13 C14 1.8(10) . . . . ?
C12 C13 C14 C15 -0.8(10) . . . . ?
C13 C14 C15 C10 -0.4(10) . . . . ?
C15 C10 C11 C12 0.5(9) . . . . ?
C18 C1 C2 C3 176.2(8) . . . . ?
B1 N1 C1 C2 177.8(7) . . . . ?
B1 N1 C1 C18 -0.2(11) . . . . ?
B1 N1 C4 C3 -176.9(6) . . . . ?
B1 N1 C4 C5 0.5(10) . . . . ?
B1 N2 C6 C5 -6.4(9) . . . . ?
B1 N2 C6 C7 178.0(6) . . . . ?
B1 N2 C9 C8 -178.1(6) . . . . ?
B1 N2 C9 C16 4.2(10) . . . . ?

_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_19gtu089_bc_bt_36_0ma
_database_code_depnum_ccdc_archive 'CCDC 2108985'
loop_
_audit_author_name
_audit_author_address
'Yunus Zorlu'
;Gebze Technical University
Turkey
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-07-12 downloaded from the CCDC.
;
_audit_creation_date             2021-09-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 B F2 I3 N2'
_chemical_formula_sum            'C19 H16 B F2 I3 N2'
_chemical_formula_weight         701.85
_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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.7772(15)
_cell_length_b                   13.5103(19)
_cell_length_c                   15.027(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2188.0(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3188
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   0.716
_shelx_estimated_absorpt_T_min   0.526
_exptl_absorpt_coefficient_mu    4.308
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.131
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.00 -2.00 -1.00 0.0660
3.00 3.00 2.00 0.0660
-4.00 2.00 -3.00 0.0300
0.00 1.00 0.00 0.0530
-4.00 4.00 1.00 0.0160
-3.00 1.00 3.00 0.0160
-1.00 0.00 4.00 0.0140
3.00 -4.00 4.00 0.0660
3.00 -3.00 -1.00 0.0640
1.00 -1.00 -3.00 0.0640
0.00 0.00 -1.00 0.0410
0.00 3.00 -4.00 0.0520

_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.083
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8067
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.022
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         2.417
_diffrn_ambient_temperature      296
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1631
_reflns_number_total             1930
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.111
_refine_diff_density_min         -1.177
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1930
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.034
_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)+(0.0270P)²+4.9259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0698
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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 0.5000 1.03776(3) 0.7500 0.04826(15) Uani 1 2 d S T P . .
I2 I 0.77236(3) 0.46608(2) 0.44424(2) 0.05529(14) Uani 1 1 d . . . . .
F1 F 0.4123(2) 0.27991(18) 0.70827(19) 0.0507(7) Uani 1 1 d . . . . .
N1 N 0.5639(3) 0.4080(2) 0.6802(2) 0.0307(7) Uani 1 1 d . . . . .
C1 C 0.6270(4) 0.3794(3) 0.6060(3) 0.0337(9) Uani 1 1 d . . . . .
C2 C 0.6679(4) 0.4654(3) 0.5612(3) 0.0354(10) Uani 1 1 d . . . . .
C3 C 0.6296(4) 0.5477(3) 0.6087(3) 0.0366(10) Uani 1 1 d . . . . .
H3 H 0.6443 0.6136 0.5941 0.044 Uiso 1 1 calc R U . . .
C4 C 0.5644(4) 0.5125(3) 0.6830(3) 0.0317(9) Uani 1 1 d . . . . .
C5 C 0.5000 0.5639(4) 0.7500 0.0302(12) Uani 1 2 d S T P . .
C6 C 0.5000 0.6748(4) 0.7500 0.0303(12) Uani 1 2 d S T P . .
C7 C 0.3883(4) 0.7270(3) 0.7452(3) 0.0343(9) Uani 1 1 d . . . . .
H7 H 0.3135 0.6928 0.7423 0.041 Uiso 1 1 calc R U . . .
C8 C 0.3883(4) 0.8314(3) 0.7446(3) 0.0364(10) Uani 1 1 d . . . . .
H8 H 0.3142 0.8664 0.7406 0.044 Uiso 1 1 calc R U . . .
C9 C 0.5000 0.8811(4) 0.7500 0.0337(13) Uani 1 2 d S T P . .
C10 C 0.6417(4) 0.2732(3) 0.5779(3) 0.0434(11) Uani 1 1 d . . . . .
H10A H 0.6354 0.2309 0.6299 0.052 Uiso 1 1 calc R U . . .
H10B H 0.7235 0.2641 0.5523 0.052 Uiso 1 1 calc R U . . .
C11 C 0.5435(5) 0.2426(4) 0.5099(4) 0.0647(15) Uani 1 1 d . . . . .
H11A H 0.5519 0.2824 0.4574 0.097 Uiso 1 1 calc R U . . .
H11B H 0.4624 0.2520 0.5349 0.097 Uiso 1 1 calc R U . . .
H11C H 0.5546 0.1741 0.4948 0.097 Uiso 1 1 calc R U . . .
B1 B 0.5000 0.3389(5) 0.7500 0.0323(15) Uani 1 2 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 C9 2.117(6) . ?
I2 C2 2.088(4) . ?
F1 B1 1.387(4) . ?
N1 C1 1.361(5) . ?
N1 C4 1.412(5) . ?
N1 B1 1.564(5) . ?
C1 C2 1.413(6) . ?
C1 C10 1.504(6) . ?
C2 C3 1.384(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.403(6) . ?
C4 C5 1.406(5) . ?
C5 C4 1.406(5) 3_656 ?
C5 C6 1.498(8) . ?
C6 C7 1.398(5) . ?
C6 C7 1.398(5) 3_656 ?
C7 H7 0.9300 . ?
C7 C8 1.411(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(5) . ?
C9 C8 1.380(5) 3_656 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.528(7) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
B1 F1 1.387(4) 3_656 ?
B1 N1 1.564(5) 3_656 ?

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 107.9(3) . . ?
C1 N1 B1 126.8(3) . . ?
C4 N1 B1 125.3(3) . . ?
N1 C1 C2 108.2(3) . . ?
N1 C1 C10 123.6(4) . . ?
C2 C1 C10 128.1(4) . . ?
C1 C2 I2 125.0(3) . . ?
C3 C2 I2 126.2(3) . . ?
C3 C2 C1 108.8(4) . . ?
C2 C3 H3 126.7 . . ?
C2 C3 C4 106.7(3) . . ?
C4 C3 H3 126.7 . . ?
C3 C4 N1 108.5(3) . . ?
C3 C4 C5 130.5(4) . . ?
C5 C4 N1 120.9(4) . . ?
C4 C5 C4 120.8(5) . 3_656 ?
C4 C5 C6 119.6(3) . . ?
C4 C5 C6 119.6(3) 3_656 . ?
C7 C6 C5 120.3(3) 3_656 . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 C7 119.4(5) 3_656 . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.3(4) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.1(4) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 I1 119.1(3) 3_656 . ?
C8 C9 I1 119.1(3) . . ?
C8 C9 C8 121.9(5) . 3_656 ?
C1 C10 H10A 109.2 . . ?
C1 C10 H10B 109.2 . . ?
C1 C10 C11 111.9(4) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
F1 B1 F1 109.8(5) . 3_656 ?
F1 B1 N1 109.87(17) 3_656 3_656 ?
F1 B1 N1 110.27(16) . 3_656 ?
F1 B1 N1 109.88(17) . . ?
F1 B1 N1 110.27(16) 3_656 . ?
N1 B1 N1 106.7(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
I2 C2 C3 C4 -178.9(3) . . . . ?
N1 C1 C2 I2 178.9(3) . . . . ?
N1 C1 C2 C3 0.2(5) . . . . ?
N1 C1 C10 C11 95.3(5) . . . . ?
N1 C4 C5 C4 1.4(2) . . . 3_656 ?
N1 C4 C5 C6 -178.6(2) . . . . ?
C1 N1 C4 C3 0.0(4) . . . . ?
C1 N1 C4 C5 176.4(3) . . . . ?
C1 N1 B1 F1 62.9(5) . . . 3_656 ?
C1 N1 B1 F1 -58.2(4) . . . . ?
C1 N1 B1 N1 -177.7(4) . . . 3_656 ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C1 C10 C11 -81.3(6) . . . . ?
C2 C3 C4 N1 0.1(5) . . . . ?
C2 C3 C4 C5 -175.9(4) . . . . ?
C3 C4 C5 C4 177.0(5) . . . 3_656 ?
C3 C4 C5 C6 -3.0(5) . . . . ?
C4 N1 C1 C2 -0.1(4) . . . . ?
C4 N1 C1 C10 -177.3(4) . . . . ?
C4 N1 B1 F1 -117.9(4) . . . 3_656 ?
C4 N1 B1 F1 121.0(4) . . . . ?
C4 N1 B1 N1 1.4(2) . . . 3_656 ?
C4 C5 C6 C7 121.2(3) . . . . ?
C4 C5 C6 C7 -58.8(3) . . . 3_656 ?
C4 C5 C6 C7 121.2(3) 3_656 . . 3_656 ?
C4 C5 C6 C7 -58.8(3) 3_656 . . . ?
C5 C6 C7 C8 -179.6(3) . . . . ?
C6 C7 C8 C9 -0.8(6) . . . . ?
C7 C6 C7 C8 0.4(3) 3_656 . . . ?
C7 C8 C9 I1 -179.6(3) . . . . ?
C7 C8 C9 C8 0.4(3) . . . 3_656 ?
C10 C1 C2 I2 -4.1(6) . . . . ?
C10 C1 C2 C3 177.2(4) . . . . ?
B1 N1 C1 C2 179.2(3) . . . . ?
B1 N1 C1 C10 2.0(6) . . . . ?
B1 N1 C4 C3 -179.3(3) . . . . ?
B1 N1 C4 C5 -2.9(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
