# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2025

####################################################################### 
# 
# 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. 
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data_bophy_aldehyde_a
_database_code_depnum_ccdc_archive 'CCDC 2462994'
loop_
_audit_author_name
_audit_author_address
'Victor Nemykin'
;University of Tennessee Knoxville
United States of America
;
_audit_update_record             
;
2025-06-10 deposited with the CCDC.	2025-10-16 downloaded from the CCDC.
;
_audit_creation_date             2024-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1.333(C14 H14 B2 F4 N4 O)'
_chemical_formula_sum            'C18.67 H18.67 B2.67 F5.33 N5.33 O1.33'
_chemical_formula_weight         469.21
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.5405(7)
_cell_length_b                   9.9104(6)
_cell_length_c                   25.9429(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2967.1(3)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.82
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.945
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1495 before and 0.0729 after correction.
The Ratio of minimum to maximum transmission is 0.8129.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.357
_exptl_crystal_size_min          0.036
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            30444
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.336
_diffrn_reflns_theta_min         2.362
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3166
_reflns_number_total             3695
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.454
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3695
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0559
_refine_ls_restrained_S_all      1.128
_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)+(0.0629P)²+3.7206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1418
_refine_ls_wR_factor_ref         0.1477
_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:
 C3(H3), C5(H5), C6(H6), C9(H9), C14(H14)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_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
C1 C 0.34686(17) 0.41455(19) 0.64538(7) 0.0122(4) Uani 1 1 d . . . . .
C2 C 0.31832(18) 0.4538(2) 0.69637(7) 0.0145(4) Uani 1 1 d . . . . .
C3 C 0.40203(19) 0.3951(2) 0.72771(8) 0.0162(4) Uani 1 1 d . . . . .
H3 H 0.406856 0.403761 0.764120 0.019 Uiso 1 1 calc R U . . .
C4 C 0.47847(18) 0.32068(19) 0.69638(7) 0.0143(4) Uani 1 1 d . . . . .
C5 C 0.29696(17) 0.45237(19) 0.59899(7) 0.0122(4) Uani 1 1 d . . . . .
H5 H 0.230539 0.508834 0.600606 0.015 Uiso 1 1 calc R U . . .
C6 C 0.47218(17) 0.30266(19) 0.50405(7) 0.0119(4) Uani 1 1 d . . . . .
H6 H 0.537755 0.244851 0.502561 0.014 Uiso 1 1 calc R U . . .
C7 C 0.42760(16) 0.35079(18) 0.45720(7) 0.0111(4) Uani 1 1 d . . . . .
C8 C 0.46506(18) 0.32426(19) 0.40621(7) 0.0123(4) Uani 1 1 d . . . . .
C9 C 0.38826(18) 0.39248(19) 0.37422(7) 0.0136(4) Uani 1 1 d . . . . .
H9 H 0.390605 0.394441 0.337628 0.016 Uiso 1 1 calc R U . . .
C10 C 0.30668(18) 0.45793(19) 0.40554(7) 0.0127(4) Uani 1 1 d . . . . .
C11 C 0.21834(19) 0.5410(2) 0.71198(8) 0.0199(4) Uani 1 1 d . . . . .
H11A H 0.229145 0.632054 0.698012 0.030 Uiso 1 1 calc R U . . .
H11B H 0.214239 0.545543 0.749675 0.030 Uiso 1 1 calc R U . . .
H11C H 0.146214 0.502640 0.698479 0.030 Uiso 1 1 calc R U . . .
C12 C 0.5809(2) 0.2399(2) 0.71232(8) 0.0215(4) Uani 1 1 d . . . . .
H12A H 0.651736 0.283664 0.699896 0.032 Uiso 1 1 calc R U . . .
H12B H 0.575284 0.149080 0.697562 0.032 Uiso 1 1 calc R U . . .
H12C H 0.583223 0.233612 0.750003 0.032 Uiso 1 1 calc R U . . .
C13 C 0.56504(18) 0.2374(2) 0.39054(8) 0.0166(4) Uani 1 1 d . . . . .
H13A H 0.632357 0.258591 0.412098 0.025 Uiso 1 1 calc R U . . .
H13B H 0.584005 0.254596 0.354303 0.025 Uiso 1 1 calc R U . . .
H13C H 0.544261 0.142258 0.394936 0.025 Uiso 1 1 calc R U . . .
C14 C 0.20770(19) 0.5409(2) 0.38983(8) 0.0162(4) Uani 1 1 d . . . . .
H14 H 0.160230 0.580515 0.415645 0.019 Uiso 1 1 calc R U . . .
B1 B 0.48399(19) 0.2543(2) 0.59898(8) 0.0116(4) Uani 1 1 d . . . . .
B2 B 0.26707(19) 0.4805(2) 0.50419(8) 0.0115(4) Uani 1 1 d . . . . .
F1 F 0.60194(10) 0.25129(12) 0.59324(4) 0.0148(3) Uani 1 1 d . . . . .
F2 F 0.43877(11) 0.12477(11) 0.59968(4) 0.0161(3) Uani 1 1 d . . . . .
F3 F 0.15343(10) 0.43719(12) 0.50554(4) 0.0149(3) Uani 1 1 d . . . . .
F4 F 0.27049(11) 0.61956(11) 0.50961(4) 0.0147(3) Uani 1 1 d . . . . .
N1 N 0.44468(15) 0.33261(16) 0.64663(6) 0.0121(3) Uani 1 1 d . . . . .
N2 N 0.43019(14) 0.33142(16) 0.54980(6) 0.0106(3) Uani 1 1 d . . . . .
N3 N 0.33384(14) 0.41662(16) 0.55255(6) 0.0107(3) Uani 1 1 d . . . . .
N4 N 0.33087(14) 0.43289(16) 0.45592(6) 0.0110(3) Uani 1 1 d . . . . .
O1 O 0.18464(17) 0.56058(18) 0.34499(7) 0.0303(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
C1 C2 1.418(3) . ?
C1 C5 1.386(3) . ?
C1 N1 1.391(3) . ?
C2 C3 1.390(3) . ?
C2 C11 1.498(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.408(3) . ?
C4 C12 1.487(3) . ?
C4 N1 1.353(2) . ?
C5 H5 0.9500 . ?
C5 N3 1.326(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.403(3) . ?
C6 N2 1.313(2) . ?
C7 C8 1.416(3) . ?
C7 N4 1.382(2) . ?
C8 C9 1.390(3) . ?
C8 C13 1.496(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.403(3) . ?
C10 C14 1.466(3) . ?
C10 N4 1.359(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 0.9500 . ?
C14 O1 1.209(3) . ?
B1 F1 1.370(2) . ?
B1 F2 1.386(2) . ?
B1 N1 1.529(3) . ?
B1 N2 1.612(3) . ?
B2 F3 1.380(2) . ?
B2 F4 1.386(2) . ?
B2 N3 1.603(3) . ?
B2 N4 1.527(3) . ?
N2 N3 1.398(2) . ?

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
C5 C1 C2 129.76(19) . . ?
C5 C1 N1 121.03(17) . . ?
N1 C1 C2 109.08(17) . . ?
C1 C2 C11 126.14(18) . . ?
C3 C2 C1 105.64(17) . . ?
C3 C2 C11 128.21(18) . . ?
C2 C3 H3 125.8 . . ?
C2 C3 C4 108.46(18) . . ?
C4 C3 H3 125.8 . . ?
C3 C4 C12 128.30(18) . . ?
N1 C4 C3 108.92(18) . . ?
N1 C4 C12 122.78(18) . . ?
C1 C5 H5 117.2 . . ?
N3 C5 C1 125.69(18) . . ?
N3 C5 H5 117.2 . . ?
C7 C6 H6 117.5 . . ?
N2 C6 H6 117.5 . . ?
N2 C6 C7 125.01(18) . . ?
C6 C7 C8 129.34(18) . . ?
N4 C7 C6 121.14(17) . . ?
N4 C7 C8 109.48(16) . . ?
C7 C8 C13 126.60(17) . . ?
C9 C8 C7 105.83(17) . . ?
C9 C8 C13 127.55(17) . . ?
C8 C9 H9 126.1 . . ?
C8 C9 C10 107.89(17) . . ?
C10 C9 H9 126.1 . . ?
C9 C10 C14 128.43(17) . . ?
N4 C10 C9 109.56(17) . . ?
N4 C10 C14 122.01(17) . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14 119.0 . . ?
O1 C14 C10 121.98(19) . . ?
O1 C14 H14 119.0 . . ?
F1 B1 F2 110.82(17) . . ?
F1 B1 N1 113.19(16) . . ?
F1 B1 N2 107.89(15) . . ?
F2 B1 N1 110.36(16) . . ?
F2 B1 N2 107.74(15) . . ?
N1 B1 N2 106.57(15) . . ?
F3 B2 F4 109.50(16) . . ?
F3 B2 N3 108.30(15) . . ?
F3 B2 N4 112.51(16) . . ?
F4 B2 N3 107.43(15) . . ?
F4 B2 N4 112.13(16) . . ?
N4 B2 N3 106.74(15) . . ?
C1 N1 B1 121.22(16) . . ?
C4 N1 C1 107.89(16) . . ?
C4 N1 B1 129.90(17) . . ?
C6 N2 B1 118.06(16) . . ?
C6 N2 N3 118.08(15) . . ?
N3 N2 B1 123.53(15) . . ?
C5 N3 B2 116.84(16) . . ?
C5 N3 N2 117.59(16) . . ?
N2 N3 B2 125.52(14) . . ?
C7 N4 B2 123.48(15) . . ?
C10 N4 C7 107.25(16) . . ?
C10 N4 B2 129.26(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.7(2) . . . . ?
C1 C5 N3 B2 -176.17(18) . . . . ?
C1 C5 N3 N2 1.2(3) . . . . ?
C2 C1 C5 N3 175.7(2) . . . . ?
C2 C1 N1 C4 -0.6(2) . . . . ?
C2 C1 N1 B1 169.06(17) . . . . ?
C2 C3 C4 C12 -179.5(2) . . . . ?
C2 C3 C4 N1 0.4(2) . . . . ?
C3 C4 N1 C1 0.1(2) . . . . ?
C3 C4 N1 B1 -168.34(19) . . . . ?
C5 C1 C2 C3 -175.0(2) . . . . ?
C5 C1 C2 C11 4.7(4) . . . . ?
C5 C1 N1 C4 175.67(18) . . . . ?
C5 C1 N1 B1 -14.7(3) . . . . ?
C6 C7 C8 C9 177.6(2) . . . . ?
C6 C7 C8 C13 -0.9(3) . . . . ?
C6 C7 N4 C10 -177.66(18) . . . . ?
C6 C7 N4 B2 1.6(3) . . . . ?
C6 N2 N3 C5 -175.52(17) . . . . ?
C6 N2 N3 B2 1.6(3) . . . . ?
C7 C6 N2 B1 173.52(18) . . . . ?
C7 C6 N2 N3 -0.1(3) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C7 N4 C10 0.2(2) . . . . ?
C8 C7 N4 B2 179.45(17) . . . . ?
C8 C9 C10 C14 -179.13(19) . . . . ?
C8 C9 C10 N4 0.3(2) . . . . ?
C9 C10 C14 O1 1.1(3) . . . . ?
C9 C10 N4 C7 -0.3(2) . . . . ?
C9 C10 N4 B2 -179.49(18) . . . . ?
C11 C2 C3 C4 179.5(2) . . . . ?
C12 C4 N1 C1 -179.95(19) . . . . ?
C12 C4 N1 B1 11.6(3) . . . . ?
C13 C8 C9 C10 178.38(19) . . . . ?
C14 C10 N4 C7 179.16(18) . . . . ?
C14 C10 N4 B2 0.0(3) . . . . ?
B1 N2 N3 C5 11.2(3) . . . . ?
B1 N2 N3 B2 -171.68(16) . . . . ?
F1 B1 N1 C1 141.20(18) . . . . ?
F1 B1 N1 C4 -51.7(3) . . . . ?
F1 B1 N2 C6 43.0(2) . . . . ?
F1 B1 N2 N3 -143.72(16) . . . . ?
F2 B1 N1 C1 -93.9(2) . . . . ?
F2 B1 N1 C4 73.2(3) . . . . ?
F2 B1 N2 C6 -76.7(2) . . . . ?
F2 B1 N2 N3 96.59(19) . . . . ?
F3 B2 N3 C5 -62.8(2) . . . . ?
F3 B2 N3 N2 120.02(18) . . . . ?
F3 B2 N4 C7 -118.92(19) . . . . ?
F3 B2 N4 C10 60.1(3) . . . . ?
F4 B2 N3 C5 55.3(2) . . . . ?
F4 B2 N3 N2 -121.79(18) . . . . ?
F4 B2 N4 C7 117.12(19) . . . . ?
F4 B2 N4 C10 -63.8(3) . . . . ?
N1 C1 C2 C3 0.8(2) . . . . ?
N1 C1 C2 C11 -179.42(19) . . . . ?
N1 C1 C5 N3 0.3(3) . . . . ?
N1 B1 N2 C6 164.87(16) . . . . ?
N1 B1 N2 N3 -21.9(2) . . . . ?
N2 C6 C7 C8 -178.86(19) . . . . ?
N2 C6 C7 N4 -1.5(3) . . . . ?
N2 B1 N1 C1 22.8(2) . . . . ?
N2 B1 N1 C4 -170.12(18) . . . . ?
N3 B2 N4 C7 -0.3(2) . . . . ?
N3 B2 N4 C10 178.80(17) . . . . ?
N4 C7 C8 C9 0.0(2) . . . . ?
N4 C7 C8 C13 -178.58(18) . . . . ?
N4 C10 C14 O1 -178.2(2) . . . . ?
N4 B2 N3 C5 175.80(16) . . . . ?
N4 B2 N3 N2 -1.3(2) . . . . ?

_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_mo_dijo_tmbophy_alkyne_frn_2_r_a
_database_code_depnum_ccdc_archive 'CCDC 2464599'
loop_
_audit_author_name
_audit_author_address
'Victor Victor Nemykin'
;University of Tennessee Knoxville
United States of America
;
_audit_update_record             
;
2025-06-16 deposited with the CCDC.	2025-10-16 downloaded from the CCDC.
;
_audit_creation_date             2024-10-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 B F2 N4 O'
_chemical_formula_sum            'C14 H15 B F2 N4 O'
_chemical_formula_weight         304.11
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   7.5311(4)
_cell_length_b                   20.6790(12)
_cell_length_c                   9.2357(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.939(2)
_cell_angle_gamma                90
_cell_volume                     1416.74(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4797
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1441 before and 0.0750 after correction.
The Ratio of minimum to maximum transmission is 0.9218.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.096
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21068
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.729
_diffrn_reflns_theta_min         2.446
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2279
_reflns_number_total             3005
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0453
_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)+(0.0418P)²+0.9107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1171
_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:
 C3(H3), C5(H5), C8(H8), C11(H11), C14(H14)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.5968(2) 0.34326(9) 0.4792(2) 0.0221(4) Uani 1 1 d . . . . .
C2 C 0.6060(3) 0.29005(9) 0.3874(2) 0.0257(4) Uani 1 1 d . . . . .
C3 C 0.7813(3) 0.26577(9) 0.4247(2) 0.0286(4) Uani 1 1 d . . . . .
H3 H 0.828150 0.229273 0.381391 0.034 Uiso 1 1 calc R U . . .
C4 C 0.8750(3) 0.30397(9) 0.5353(2) 0.0257(4) Uani 1 1 d . . . . .
C5 C 0.4539(2) 0.38553(9) 0.4916(2) 0.0232(4) Uani 1 1 d . . . . .
H5 H 0.344357 0.377975 0.425715 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4586(3) 0.26440(10) 0.2729(2) 0.0337(5) Uani 1 1 d . . . . .
H6A H 0.500451 0.262355 0.178210 0.051 Uiso 1 1 calc R U . . .
H6B H 0.353619 0.293038 0.264299 0.051 Uiso 1 1 calc R U . . .
H6C H 0.424931 0.220964 0.300836 0.051 Uiso 1 1 calc R U . . .
C7 C 1.0652(3) 0.29790(11) 0.6119(2) 0.0333(5) Uani 1 1 d . . . . .
H7A H 1.131697 0.269751 0.554730 0.050 Uiso 1 1 calc R U . . .
H7B H 1.067396 0.279196 0.709723 0.050 Uiso 1 1 calc R U . . .
H7C H 1.121513 0.340753 0.621740 0.050 Uiso 1 1 calc R U . . .
C8 C 0.6209(3) 0.49032(9) 0.7740(2) 0.0240(4) Uani 1 1 d . . . . .
H8 H 0.733432 0.496611 0.836950 0.029 Uiso 1 1 calc R U . . .
C9 C 0.4811(3) 0.53209(9) 0.7991(2) 0.0239(4) Uani 1 1 d . . . . .
C10 C 0.4946(3) 0.57995(10) 0.9101(2) 0.0272(4) Uani 1 1 d . . . . .
C11 C 0.3258(3) 0.60860(10) 0.8963(2) 0.0281(4) Uani 1 1 d . . . . .
H11 H 0.293142 0.642310 0.956504 0.034 Uiso 1 1 calc R U . . .
C12 C 0.2126(3) 0.57960(9) 0.7796(2) 0.0250(4) Uani 1 1 d . . . . .
C13 C 0.6613(3) 0.59698(11) 1.0184(2) 0.0338(5) Uani 1 1 d . . . . .
H13A H 0.626372 0.616039 1.106489 0.051 Uiso 1 1 calc R U . . .
H13B H 0.733477 0.628192 0.973631 0.051 Uiso 1 1 calc R U . . .
H13C H 0.732509 0.557809 1.045537 0.051 Uiso 1 1 calc R U . . .
C14 C 0.0253(3) 0.59330(10) 0.7157(2) 0.0277(4) Uani 1 1 d . . . . .
H14 H -0.026314 0.570890 0.628819 0.033 Uiso 1 1 calc R U . . .
B1 B 0.8059(3) 0.40885(11) 0.6691(2) 0.0241(5) Uani 1 1 d . . . . .
F1 F 0.88581(15) 0.39299(6) 0.81008(12) 0.0360(3) Uani 1 1 d . . . . .
F2 F 0.91332(15) 0.45368(6) 0.61115(13) 0.0344(3) Uani 1 1 d . . . . .
N1 N 0.7629(2) 0.35116(7) 0.56973(17) 0.0228(4) Uani 1 1 d . . . . .
N2 N 0.6180(2) 0.44426(7) 0.67680(17) 0.0225(3) Uani 1 1 d . . . . .
N3 N 0.4530(2) 0.43387(8) 0.58249(17) 0.0242(4) Uani 1 1 d . . . . .
N4 N 0.3082(2) 0.53325(8) 0.72197(18) 0.0242(4) Uani 1 1 d . . . . .
O1 O -0.06809(19) 0.63183(7) 0.76775(17) 0.0361(4) Uani 1 1 d . . . . .
H4 H 0.267(3) 0.5051(12) 0.644(3) 0.044(7) Uiso 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
C1 C2 1.398(3) . ?
C1 C5 1.406(3) . ?
C1 N1 1.390(2) . ?
C2 C3 1.399(3) . ?
C2 C6 1.493(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C4 C7 1.489(3) . ?
C4 N1 1.363(2) . ?
C5 H5 0.9500 . ?
C5 N3 1.306(2) . ?
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 H8 0.9500 . ?
C8 C9 1.411(3) . ?
C8 N2 1.307(2) . ?
C9 C10 1.416(3) . ?
C9 N4 1.372(3) . ?
C10 C11 1.389(3) . ?
C10 C13 1.506(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(3) . ?
C12 C14 1.460(3) . ?
C12 N4 1.361(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 0.9500 . ?
C14 O1 1.216(2) . ?
B1 F1 1.377(2) . ?
B1 F2 1.396(2) . ?
B1 N1 1.506(3) . ?
B1 N2 1.606(3) . ?
N2 N3 1.406(2) . ?
N4 H4 0.94(3) . ?

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
C2 C1 C5 131.12(18) . . ?
N1 C1 C2 108.88(16) . . ?
N1 C1 C5 120.00(17) . . ?
C1 C2 C3 106.08(17) . . ?
C1 C2 C6 126.93(18) . . ?
C3 C2 C6 126.99(18) . . ?
C2 C3 H3 125.8 . . ?
C4 C3 C2 108.41(17) . . ?
C4 C3 H3 125.8 . . ?
C3 C4 C7 128.92(18) . . ?
N1 C4 C3 108.86(17) . . ?
N1 C4 C7 122.21(18) . . ?
C1 C5 H5 115.9 . . ?
N3 C5 C1 128.13(18) . . ?
N3 C5 H5 115.9 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 H8 115.3 . . ?
N2 C8 H8 115.3 . . ?
N2 C8 C9 129.35(18) . . ?
C8 C9 C10 125.73(18) . . ?
N4 C9 C8 126.41(18) . . ?
N4 C9 C10 107.85(17) . . ?
C9 C10 C13 126.30(18) . . ?
C11 C10 C9 106.36(17) . . ?
C11 C10 C13 127.32(19) . . ?
C10 C11 H11 125.8 . . ?
C10 C11 C12 108.45(18) . . ?
C12 C11 H11 125.8 . . ?
C11 C12 C14 130.58(18) . . ?
N4 C12 C11 108.19(17) . . ?
N4 C12 C14 121.19(18) . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14 118.2 . . ?
O1 C14 C12 123.51(19) . . ?
O1 C14 H14 118.2 . . ?
F1 B1 F2 109.43(16) . . ?
F1 B1 N1 113.61(17) . . ?
F1 B1 N2 108.14(15) . . ?
F2 B1 N1 111.74(16) . . ?
F2 B1 N2 106.72(15) . . ?
N1 B1 N2 106.88(15) . . ?
C1 N1 B1 122.42(15) . . ?
C4 N1 C1 107.77(16) . . ?
C4 N1 B1 129.26(16) . . ?
C8 N2 B1 116.91(16) . . ?
C8 N2 N3 116.46(15) . . ?
N3 N2 B1 126.47(15) . . ?
C5 N3 N2 114.39(15) . . ?
C9 N4 H4 123.1(15) . . ?
C12 N4 C9 109.15(17) . . ?
C12 N4 H4 127.7(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.5(2) . . . . ?
C1 C5 N3 N2 0.9(3) . . . . ?
C2 C1 C5 N3 178.40(19) . . . . ?
C2 C1 N1 C4 0.2(2) . . . . ?
C2 C1 N1 B1 172.40(16) . . . . ?
C2 C3 C4 C7 179.90(19) . . . . ?
C2 C3 C4 N1 0.6(2) . . . . ?
C3 C4 N1 C1 -0.5(2) . . . . ?
C3 C4 N1 B1 -171.99(18) . . . . ?
C5 C1 C2 C3 -179.18(19) . . . . ?
C5 C1 C2 C6 0.9(3) . . . . ?
C5 C1 N1 C4 179.65(16) . . . . ?
C5 C1 N1 B1 -8.2(3) . . . . ?
C6 C2 C3 C4 179.47(19) . . . . ?
C7 C4 N1 C1 -179.85(17) . . . . ?
C7 C4 N1 B1 8.7(3) . . . . ?
C8 C9 C10 C11 -179.00(18) . . . . ?
C8 C9 C10 C13 2.4(3) . . . . ?
C8 C9 N4 C12 179.28(18) . . . . ?
C8 N2 N3 C5 -177.04(16) . . . . ?
C9 C8 N2 B1 175.50(18) . . . . ?
C9 C8 N2 N3 -0.1(3) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C10 C9 N4 C12 -0.1(2) . . . . ?
C10 C11 C12 C14 -177.27(19) . . . . ?
C10 C11 C12 N4 0.5(2) . . . . ?
C11 C12 C14 O1 -6.4(3) . . . . ?
C11 C12 N4 C9 -0.3(2) . . . . ?
C13 C10 C11 C12 178.11(19) . . . . ?
C14 C12 N4 C9 177.75(17) . . . . ?
B1 N2 N3 C5 7.8(2) . . . . ?
F1 B1 N1 C1 133.04(17) . . . . ?
F1 B1 N1 C4 -56.6(3) . . . . ?
F1 B1 N2 C8 47.7(2) . . . . ?
F1 B1 N2 N3 -137.15(17) . . . . ?
F2 B1 N1 C1 -102.55(19) . . . . ?
F2 B1 N1 C4 67.8(2) . . . . ?
F2 B1 N2 C8 -69.9(2) . . . . ?
F2 B1 N2 N3 105.20(19) . . . . ?
N1 C1 C2 C3 0.2(2) . . . . ?
N1 C1 C2 C6 -179.79(18) . . . . ?
N1 C1 C5 N3 -0.9(3) . . . . ?
N1 B1 N2 C8 170.39(15) . . . . ?
N1 B1 N2 N3 -14.5(2) . . . . ?
N2 C8 C9 C10 178.25(19) . . . . ?
N2 C8 C9 N4 -1.0(3) . . . . ?
N2 B1 N1 C1 13.9(2) . . . . ?
N2 B1 N1 C4 -175.77(17) . . . . ?
N4 C9 C10 C11 0.4(2) . . . . ?
N4 C9 C10 C13 -178.28(18) . . . . ?
N4 C12 C14 O1 176.13(18) . . . . ?

_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_tmbophy_cpd9_a
_database_code_depnum_ccdc_archive 'CCDC 2464601'
loop_
_audit_author_name
_audit_author_address
'Victor Victor Nemykin'
;University of Tennessee Knoxville
United States of America
;
_audit_update_record             
;
2025-06-16 deposited with the CCDC.	2025-10-16 downloaded from the CCDC.
;
_audit_creation_date             2025-06-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 B2 F4 N5 O'
_chemical_formula_sum            'C21 H21 B2 F4 N5 O'
_chemical_formula_weight         457.05
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   9.2694(7)
_cell_length_b                   32.322(2)
_cell_length_c                   7.3866(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.807(2)
_cell_angle_gamma                90
_cell_volume                     2040.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3396
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1451 before and 0.0864 after correction.
The Ratio of minimum to maximum transmission is 0.8747.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.021
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1523
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            40713
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.730
_diffrn_reflns_theta_min         2.384
_diffrn_ambient_temperature      100.00
_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       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3335
_reflns_number_total             4338
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1457
_refine_ls_R_factor_gt           0.1121
_refine_ls_restrained_S_all      1.226
_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)+(0.0336P)²+7.0229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1849
_refine_ls_wR_factor_ref         0.1970
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C8(H8), C12(H12), C14(H14), C16(H16), C19(H19), N1(H1)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_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
C1 C -0.0762(5) 0.44881(13) 0.3938(6) 0.0137(9) Uani 1 1 d . . . . .
C2 C -0.2061(5) 0.46086(13) 0.4314(7) 0.0171(9) Uani 1 1 d . . . . .
H2 H -0.238886 0.448840 0.526492 0.020 Uiso 1 1 calc R U . . .
C3 C -0.2798(5) 0.49334(13) 0.3069(6) 0.0151(9) Uani 1 1 d . . . . .
C4 C -0.1933(5) 0.50103(14) 0.1937(6) 0.0162(9) Uani 1 1 d . . . . .
C5 C 0.0359(5) 0.41629(13) 0.4863(6) 0.0138(9) Uani 1 1 d . . . . .
H5 H 0.024664 0.401849 0.592041 0.017 Uiso 1 1 calc R U . . .
C6 C 0.1542(5) 0.40479(13) 0.4354(6) 0.0136(9) Uani 1 1 d . . . . .
H6 H 0.165756 0.418794 0.328737 0.016 Uiso 1 1 calc R U . . .
C7 C 0.2652(4) 0.37249(13) 0.5324(6) 0.0126(9) Uani 1 1 d . . . . .
C8 C 0.2779(5) 0.34758(13) 0.6949(6) 0.0130(9) Uani 1 1 d . . . . .
H8 H 0.213324 0.349207 0.767942 0.016 Uiso 1 1 calc R U . . .
C9 C 0.4003(5) 0.32056(13) 0.7289(6) 0.0131(9) Uani 1 1 d . . . . .
C10 C 0.4662(5) 0.32980(13) 0.5899(6) 0.0125(9) Uani 1 1 d . . . . .
C11 C -0.4228(5) 0.51634(15) 0.2976(7) 0.0220(10) Uani 1 1 d . . . . .
H11A H -0.500725 0.496647 0.305081 0.033 Uiso 1 1 calc R U . . .
H11B H -0.466686 0.531697 0.173767 0.033 Uiso 1 1 calc R U . . .
H11C H -0.394642 0.535729 0.408016 0.033 Uiso 1 1 calc R U . . .
C12 C -0.2128(6) 0.53225(17) 0.0508(8) 0.0301(12) Uani 1 1 d . . . . .
H12 H -0.299652 0.550348 0.021958 0.036 Uiso 1 1 calc R U . . .
C13 C 0.4542(5) 0.28699(14) 0.8833(6) 0.0177(10) Uani 1 1 d . . . . .
H13A H 0.411888 0.292311 0.983864 0.027 Uiso 1 1 calc R U . . .
H13B H 0.568797 0.286819 0.944362 0.027 Uiso 1 1 calc R U . . .
H13C H 0.416854 0.260081 0.821914 0.027 Uiso 1 1 calc R U . . .
C14 C 0.5952(5) 0.31349(13) 0.5649(6) 0.0133(9) Uani 1 1 d . . . . .
H14 H 0.649037 0.291563 0.649856 0.016 Uiso 1 1 calc R U . . .
C15 C 0.7571(5) 0.35532(13) 0.1517(6) 0.0162(9) Uani 1 1 d . . . . .
C16 C 0.6295(5) 0.37155(14) 0.1803(6) 0.0145(9) Uani 1 1 d . . . . .
H16 H 0.576871 0.394147 0.099400 0.017 Uiso 1 1 calc R U . . .
C17 C 0.9559(5) 0.31310(14) 0.2024(6) 0.0183(10) Uani 1 1 d . . . . .
C18 C 0.8223(5) 0.36612(15) 0.0131(6) 0.0199(10) Uani 1 1 d . . . . .
C19 C 0.9454(5) 0.33937(14) 0.0485(6) 0.0184(10) Uani 1 1 d . . . . .
H19 H 1.012709 0.338876 -0.021024 0.022 Uiso 1 1 calc R U . . .
C20 C 1.0717(5) 0.27969(15) 0.2959(7) 0.0236(11) Uani 1 1 d . . . . .
H20A H 1.019505 0.252729 0.264474 0.035 Uiso 1 1 calc R U . . .
H20B H 1.116445 0.283594 0.438609 0.035 Uiso 1 1 calc R U . . .
H20C H 1.155460 0.280769 0.246047 0.035 Uiso 1 1 calc R U . . .
C21 C 0.7690(6) 0.39987(16) -0.1353(7) 0.0283(12) Uani 1 1 d . . . . .
H21A H 0.659333 0.406495 -0.162525 0.042 Uiso 1 1 calc R U . . .
H21B H 0.778734 0.390849 -0.256675 0.042 Uiso 1 1 calc R U . . .
H21C H 0.833703 0.424503 -0.084303 0.042 Uiso 1 1 calc R U . . .
B1 B 0.4163(5) 0.37979(15) 0.3027(7) 0.0143(10) Uani 1 1 d . . . . .
B2 B 0.8074(6) 0.30455(16) 0.4345(7) 0.0154(10) Uani 1 1 d . . . . .
F1 F 0.7799(3) 0.26245(8) 0.4132(4) 0.0232(6) Uani 1 1 d . . . . .
F2 F 0.3008(3) 0.37090(10) 0.1232(4) 0.0295(7) Uani 1 1 d . . . . .
F3 F 0.4436(3) 0.42160(8) 0.3223(4) 0.0266(7) Uani 1 1 d . . . . .
F4 F 0.9244(3) 0.31277(9) 0.6150(4) 0.0232(6) Uani 1 1 d . . . . .
N1 N -0.0707(4) 0.47346(11) 0.2478(5) 0.0150(8) Uani 1 1 d . . . . .
H1 H 0.000028 0.472024 0.195872 0.018 Uiso 1 1 calc R U . . .
N2 N 0.3809(4) 0.36177(10) 0.4715(5) 0.0118(7) Uani 1 1 d . . . . .
N3 N 0.6503(4) 0.32583(10) 0.4325(5) 0.0125(7) Uani 1 1 d . . . . .
N4 N 0.5741(4) 0.35836(11) 0.3107(5) 0.0139(8) Uani 1 1 d . . . . .
N5 N 0.8419(4) 0.32270(11) 0.2667(5) 0.0151(8) Uani 1 1 d . . . . .
O1 O -0.1268(5) 0.53787(13) -0.0391(6) 0.0466(12) 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
C1 C2 1.392(6) . ?
C1 C5 1.449(6) . ?
C1 N1 1.358(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(6) . ?
C3 C4 1.387(6) . ?
C3 C11 1.499(6) . ?
C4 C12 1.420(6) . ?
C4 N1 1.375(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.342(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.446(6) . ?
C7 C8 1.412(6) . ?
C7 N2 1.358(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.375(6) . ?
C9 C10 1.415(6) . ?
C9 C13 1.512(6) . ?
C10 C14 1.383(6) . ?
C10 N2 1.386(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 0.9500 . ?
C12 O1 1.233(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 0.9500 . ?
C14 N3 1.328(5) . ?
C15 C16 1.384(6) . ?
C15 C18 1.419(6) . ?
C15 N5 1.391(5) . ?
C16 H16 0.9500 . ?
C16 N4 1.325(5) . ?
C17 C19 1.391(6) . ?
C17 C20 1.491(6) . ?
C17 N5 1.351(6) . ?
C18 C19 1.373(6) . ?
C18 C21 1.489(7) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
B1 F2 1.374(5) . ?
B1 F3 1.372(6) . ?
B1 N2 1.523(6) . ?
B1 N4 1.599(6) . ?
B2 F1 1.382(6) . ?
B2 F4 1.379(5) . ?
B2 N3 1.606(6) . ?
B2 N5 1.513(6) . ?
N1 H1 0.8800 . ?
N3 N4 1.386(5) . ?

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
C2 C1 C5 128.8(4) . . ?
N1 C1 C2 107.2(4) . . ?
N1 C1 C5 124.0(4) . . ?
C1 C2 H2 125.6 . . ?
C3 C2 C1 108.7(4) . . ?
C3 C2 H2 125.6 . . ?
C2 C3 C11 127.2(4) . . ?
C4 C3 C2 106.5(4) . . ?
C4 C3 C11 126.3(4) . . ?
C3 C4 C12 129.7(4) . . ?
N1 C4 C3 108.3(4) . . ?
N1 C4 C12 121.9(4) . . ?
C1 C5 H5 117.2 . . ?
C6 C5 C1 125.7(4) . . ?
C6 C5 H5 117.2 . . ?
C5 C6 H6 117.9 . . ?
C5 C6 C7 124.3(4) . . ?
C7 C6 H6 117.9 . . ?
C8 C7 C6 129.9(4) . . ?
N2 C7 C6 121.4(4) . . ?
N2 C7 C8 108.6(4) . . ?
C7 C8 H8 126.0 . . ?
C9 C8 C7 108.0(4) . . ?
C9 C8 H8 126.0 . . ?
C8 C9 C10 106.9(4) . . ?
C8 C9 C13 127.0(4) . . ?
C10 C9 C13 126.1(4) . . ?
C14 C10 C9 130.9(4) . . ?
C14 C10 N2 120.7(4) . . ?
N2 C10 C9 108.3(3) . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C12 H12 117.2 . . ?
O1 C12 C4 125.6(4) . . ?
O1 C12 H12 117.2 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14 117.2 . . ?
N3 C14 C10 125.7(4) . . ?
N3 C14 H14 117.2 . . ?
C16 C15 C18 130.2(4) . . ?
C16 C15 N5 120.6(4) . . ?
N5 C15 C18 109.2(4) . . ?
C15 C16 H16 117.1 . . ?
N4 C16 C15 125.7(4) . . ?
N4 C16 H16 117.1 . . ?
C19 C17 C20 129.1(4) . . ?
N5 C17 C19 109.3(4) . . ?
N5 C17 C20 121.6(4) . . ?
C15 C18 C21 126.8(4) . . ?
C19 C18 C15 105.2(4) . . ?
C19 C18 C21 128.0(4) . . ?
C17 C19 H19 125.4 . . ?
C18 C19 C17 109.3(4) . . ?
C18 C19 H19 125.4 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F2 B1 N2 112.0(4) . . ?
F2 B1 N4 107.8(4) . . ?
F3 B1 F2 110.5(4) . . ?
F3 B1 N2 112.3(4) . . ?
F3 B1 N4 107.1(3) . . ?
N2 B1 N4 106.8(3) . . ?
F1 B2 N3 107.1(3) . . ?
F1 B2 N5 112.1(4) . . ?
F4 B2 F1 110.0(4) . . ?
F4 B2 N3 107.3(3) . . ?
F4 B2 N5 112.3(4) . . ?
N5 B2 N3 107.8(3) . . ?
C1 N1 C4 109.3(3) . . ?
C1 N1 H1 125.4 . . ?
C4 N1 H1 125.4 . . ?
C7 N2 C10 108.2(3) . . ?
C7 N2 B1 128.5(3) . . ?
C10 N2 B1 123.4(3) . . ?
C14 N3 B2 118.1(3) . . ?
C14 N3 N4 117.5(3) . . ?
N4 N3 B2 124.3(3) . . ?
C16 N4 B1 116.1(3) . . ?
C16 N4 N3 118.2(3) . . ?
N3 N4 B1 125.5(3) . . ?
C15 N5 B2 123.1(4) . . ?
C17 N5 C15 107.0(4) . . ?
C17 N5 B2 129.9(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.2(5) . . . . ?
C1 C2 C3 C11 -179.2(4) . . . . ?
C1 C5 C6 C7 179.2(4) . . . . ?
C2 C1 C5 C6 176.1(4) . . . . ?
C2 C1 N1 C4 0.6(5) . . . . ?
C2 C3 C4 C12 -176.5(5) . . . . ?
C2 C3 C4 N1 0.5(5) . . . . ?
C3 C4 C12 O1 177.3(5) . . . . ?
C3 C4 N1 C1 -0.7(5) . . . . ?
C5 C1 C2 C3 -179.8(4) . . . . ?
C5 C1 N1 C4 -179.8(4) . . . . ?
C5 C6 C7 C8 -1.5(7) . . . . ?
C5 C6 C7 N2 178.8(4) . . . . ?
C6 C7 C8 C9 178.4(4) . . . . ?
C6 C7 N2 C10 -179.1(4) . . . . ?
C6 C7 N2 B1 0.0(6) . . . . ?
C7 C8 C9 C10 1.8(5) . . . . ?
C7 C8 C9 C13 -177.7(4) . . . . ?
C8 C7 N2 C10 1.1(4) . . . . ?
C8 C7 N2 B1 -179.7(4) . . . . ?
C8 C9 C10 C14 176.5(4) . . . . ?
C8 C9 C10 N2 -1.1(5) . . . . ?
C9 C10 C14 N3 -177.2(4) . . . . ?
C9 C10 N2 C7 0.0(4) . . . . ?
C9 C10 N2 B1 -179.2(4) . . . . ?
C10 C14 N3 B2 176.8(4) . . . . ?
C10 C14 N3 N4 1.3(6) . . . . ?
C11 C3 C4 C12 2.5(8) . . . . ?
C11 C3 C4 N1 179.5(4) . . . . ?
C12 C4 N1 C1 176.6(4) . . . . ?
C13 C9 C10 C14 -4.0(7) . . . . ?
C13 C9 C10 N2 178.4(4) . . . . ?
C14 C10 N2 C7 -178.0(4) . . . . ?
C14 C10 N2 B1 2.9(6) . . . . ?
C14 N3 N4 C16 178.7(4) . . . . ?
C14 N3 N4 B1 -5.8(6) . . . . ?
C15 C16 N4 B1 -175.0(4) . . . . ?
C15 C16 N4 N3 0.9(6) . . . . ?
C15 C18 C19 C17 0.0(5) . . . . ?
C16 C15 C18 C19 -178.7(4) . . . . ?
C16 C15 C18 C21 2.4(8) . . . . ?
C16 C15 N5 C17 178.7(4) . . . . ?
C16 C15 N5 B2 -3.3(6) . . . . ?
C18 C15 C16 N4 177.6(4) . . . . ?
C18 C15 N5 C17 -0.3(5) . . . . ?
C18 C15 N5 B2 177.6(4) . . . . ?
C19 C17 N5 C15 0.4(5) . . . . ?
C19 C17 N5 B2 -177.4(4) . . . . ?
C20 C17 C19 C18 -178.6(4) . . . . ?
C20 C17 N5 C15 178.9(4) . . . . ?
C20 C17 N5 B2 1.1(7) . . . . ?
C21 C18 C19 C17 179.0(4) . . . . ?
B2 N3 N4 C16 3.5(6) . . . . ?
B2 N3 N4 B1 179.0(4) . . . . ?
F1 B2 N3 C14 57.2(5) . . . . ?
F1 B2 N3 N4 -127.6(4) . . . . ?
F1 B2 N5 C15 124.1(4) . . . . ?
F1 B2 N5 C17 -58.4(6) . . . . ?
F2 B1 N2 C7 -67.2(6) . . . . ?
F2 B1 N2 C10 111.8(4) . . . . ?
F2 B1 N4 C16 62.7(5) . . . . ?
F2 B1 N4 N3 -112.8(4) . . . . ?
F3 B1 N2 C7 57.9(5) . . . . ?
F3 B1 N2 C10 -123.1(4) . . . . ?
F3 B1 N4 C16 -56.2(5) . . . . ?
F3 B1 N4 N3 128.2(4) . . . . ?
F4 B2 N3 C14 -60.8(5) . . . . ?
F4 B2 N3 N4 114.4(4) . . . . ?
F4 B2 N5 C15 -111.4(4) . . . . ?
F4 B2 N5 C17 66.0(6) . . . . ?
N1 C1 C2 C3 -0.3(5) . . . . ?
N1 C1 C5 C6 -3.3(7) . . . . ?
N1 C4 C12 O1 0.6(9) . . . . ?
N2 C7 C8 C9 -1.8(5) . . . . ?
N2 C10 C14 N3 0.2(7) . . . . ?
N2 B1 N4 C16 -176.7(4) . . . . ?
N2 B1 N4 N3 7.7(5) . . . . ?
N3 B2 N5 C15 6.5(5) . . . . ?
N3 B2 N5 C17 -176.0(4) . . . . ?
N4 B1 N2 C7 175.0(4) . . . . ?
N4 B1 N2 C10 -6.0(5) . . . . ?
N5 C15 C16 N4 -1.1(7) . . . . ?
N5 C15 C18 C19 0.2(5) . . . . ?
N5 C15 C18 C21 -178.8(4) . . . . ?
N5 C17 C19 C18 -0.3(5) . . . . ?
N5 B2 N3 C14 178.0(4) . . . . ?
N5 B2 N3 N4 -6.8(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_cu_dijo_bophy_alkyne_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2464595'
loop_
_audit_author_name
_audit_author_address
'Victor Victor Nemykin'
;University of Tennessee Knoxville
United States of America
;
_audit_update_record             
;
2025-06-16 deposited with the CCDC.	2025-10-16 downloaded from the CCDC.
;
_audit_creation_date             2025-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C21 H19 B Br F2 N5)'
_chemical_formula_sum            'C42 H38 B2 Br2 F4 N10'
_chemical_formula_weight         940.26
_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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   13.1933(14)
_cell_length_b                   13.3860(13)
_cell_length_c                   13.7640(14)
_cell_angle_alpha                98.094(6)
_cell_angle_beta                 93.490(6)
_cell_angle_gamma                118.563(5)
_cell_volume                     2090.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2537
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      50.32
_cell_measurement_theta_min      5.19
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.581
_exptl_absorpt_coefficient_mu    2.985
_exptl_absorpt_correction_T_max  0.7500
_exptl_absorpt_correction_T_min  0.4755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1291 before and 0.0694 after correction.
The Ratio of minimum to maximum transmission is 0.6340.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 1.00 0.0350
-1.00 1.00 1.00 0.0320
-1.00 -1.00 0.00 0.0030
-1.00 1.00 0.00 0.0160
0.00 0.00 -1.00 0.0980
1.00 1.00 0.00 0.0050
1.00 -1.00 0.00 0.0050

_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.017
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_unetI/netI     0.1032
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9642
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        50.538
_diffrn_reflns_theta_max         50.538
_diffrn_reflns_theta_min         5.190
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_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                3007
_reflns_number_total             4192
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.086
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1330
_refine_ls_R_factor_gt           0.0957
_refine_ls_restrained_S_all      1.092
_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)+(0.0851P)²+15.7737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2081
_refine_ls_wR_factor_ref         0.2286
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C23) = Uanis(C1) = Uanis(C2) = Uanis(C4)
Uanis(C18) = Uanis(C7) = Uanis(C8) = Uanis(C9)
Uanis(C26) = Uanis(C12) = Uanis(C8) = Uanis(C15)
Uanis(C34) = Uanis(C30) = Uanis(C37) = Uanis(C38) = Uanis(C29)
Uanis(C17) = Uanis(C36)
Uanis(B2) = Uanis(B1)
Uanis(F5) = Uanis(F4) = Uanis(F2) = Uanis(F1)
Uanis(N7) = Uanis(N4) = Uanis(N3)
Uanis(N6) = Uanis(N4) = Uanis(N3) = Uanis(N2) = Uanis(N7) = Uanis(N8)
Uanis(Br2) = Uanis(Br4)
3. Others
 Sof(H38)=Sof(Br4)=1-FVAR(1)
 Sof(H34)=Sof(Br2)=FVAR(1)
 Sof(H11)=Sof(Br3)=1-FVAR(2)
 Sof(H17)=Sof(Br1)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C14(H14), C17(H17), C31(H31),
 C34(H34), C38(H38), N5(H5A), N10(H10)
4.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,
 H42B,H42C)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.0689(11) 0.4100(10) 0.6325(9) 0.0381(16) Uani 1 1 d . . . . .
C2 C 0.1493(11) 0.5268(10) 0.6591(9) 0.0381(16) Uani 1 1 d . . . . .
H2 H 0.229132 0.552152 0.680529 0.046 Uiso 1 1 calc R U . . .
C3 C 0.1116(11) 0.6048(11) 0.6540(9) 0.043(3) Uani 1 1 d . . . . .
H3 H 0.168250 0.684767 0.670149 0.052 Uiso 1 1 calc R U . . .
C4 C -0.0769(11) 0.4652(11) 0.6050(9) 0.0381(16) Uani 1 1 d . . . . .
H4 H -0.156291 0.443672 0.586547 0.046 Uiso 1 1 calc R U . . .
C5 C -0.0486(11) 0.3789(11) 0.6066(9) 0.045(3) Uani 1 1 d . . . . .
H5 H -0.107454 0.299696 0.590447 0.054 Uiso 1 1 calc R U . . .
C6 C 0.0995(10) 0.3198(11) 0.6383(8) 0.038(3) Uani 1 1 d . . . . .
C7 C 0.1247(10) 0.2442(11) 0.6373(9) 0.0354(12) Uani 1 1 d . . . . .
C8 C 0.1462(10) 0.1496(10) 0.6327(8) 0.0354(12) Uani 1 1 d . . . . .
C9 C 0.2595(10) 0.1669(10) 0.6389(9) 0.0354(12) Uani 1 1 d . . . . .
C10 C 0.3694(10) 0.2664(9) 0.6544(8) 0.032(3) Uani 1 1 d . . . . .
C11 C 0.4508(10) 0.2298(11) 0.6547(9) 0.043(3) Uani 1 1 d . . . . .
H11 H 0.533029 0.279046 0.664301 0.052 Uiso 0.174(4) 1 calc R U P A 1
C12 C 0.3926(10) 0.1072(10) 0.6383(9) 0.0354(12) Uani 1 1 d . . . . .
C13 C 0.3985(10) 0.3921(10) 0.6645(10) 0.044(3) Uani 1 1 d . . . . .
H13A H 0.383643 0.407397 0.599123 0.065 Uiso 1 1 calc R U . . .
H13B H 0.480948 0.443015 0.692264 0.065 Uiso 1 1 calc R U . . .
H13C H 0.349734 0.406906 0.708795 0.065 Uiso 1 1 calc R U . . .
C14 C -0.0367(10) -0.1513(10) 0.6116(8) 0.035(3) Uani 1 1 d . . . . .
H14 H -0.027175 -0.217673 0.607397 0.042 Uiso 1 1 calc R U . . .
C15 C -0.1489(10) -0.1706(10) 0.6105(9) 0.0354(12) Uani 1 1 d . . . . .
C16 C -0.2507(10) -0.2783(10) 0.6005(9) 0.039(3) Uani 1 1 d . . . . .
C17 C -0.3446(11) -0.2612(11) 0.6010(9) 0.039(2) Uani 1 1 d . . . . .
H17 H -0.423814 -0.320153 0.594581 0.047 Uiso 0.826(4) 1 calc R U P A 2
C18 C -0.3044(10) -0.1414(10) 0.6125(9) 0.0354(12) Uani 1 1 d . . . . .
C19 C 0.4392(10) 0.0259(11) 0.6279(9) 0.046(3) Uani 1 1 d . . . . .
H19A H 0.523540 0.069200 0.627338 0.069 Uiso 1 1 calc R U . . .
H19B H 0.401298 -0.030682 0.565661 0.069 Uiso 1 1 calc R U . . .
H19C H 0.423511 -0.014702 0.683828 0.069 Uiso 1 1 calc R U . . .
C20 C -0.2531(11) -0.3934(10) 0.5872(9) 0.045(3) Uani 1 1 d . . . . .
H20A H -0.241209 -0.414055 0.519276 0.067 Uiso 1 1 calc R U . . .
H20B H -0.328743 -0.453360 0.599309 0.067 Uiso 1 1 calc R U . . .
H20C H -0.190786 -0.387553 0.634257 0.067 Uiso 1 1 calc R U . . .
C21 C -0.3688(10) -0.0767(10) 0.6212(9) 0.040(3) Uani 1 1 d . . . . .
H21A H -0.443335 -0.120645 0.576772 0.060 Uiso 1 1 calc R U . . .
H21B H -0.322445 -0.001118 0.602930 0.060 Uiso 1 1 calc R U . . .
H21C H -0.383294 -0.065394 0.689816 0.060 Uiso 1 1 calc R U . . .
C22 C 1.3944(10) 1.0523(10) 0.8821(8) 0.034(3) Uani 1 1 d . . . . .
C23 C 1.5128(11) 1.1350(11) 0.8812(9) 0.0381(16) Uani 1 1 d . . . . .
H23 H 1.519(9) 1.217(10) 0.881(8) 0.046 Uiso 1 1 d . U . . .
C24 C 1.5896(11) 1.0951(12) 0.8728(9) 0.046(4) Uani 1 1 d . . . . .
H24 H 1.672(11) 1.163(10) 0.886(8) 0.055 Uiso 1 1 d . U . . .
C25 C 1.4535(12) 0.9107(11) 0.8703(10) 0.042(4) Uani 1 1 d . . . . .
H25 H 1.439(10) 0.840(11) 0.866(9) 0.050 Uiso 1 1 d . U . . .
C26 C 1.3667(11) 0.9385(11) 0.8761(9) 0.0354(12) Uani 1 1 d . . . . .
H26 H 1.288(9) 0.881(9) 0.882(7) 0.043 Uiso 1 1 d . U . . .
C27 C 1.3028(12) 1.0829(10) 0.8859(9) 0.039(3) Uani 1 1 d . . . . .
C28 C 1.2255(12) 1.1079(10) 0.8859(9) 0.040(3) Uani 1 1 d . . . . .
C29 C 1.1273(10) 1.1249(10) 0.8818(8) 0.0322(14) Uani 1 1 d . . . . .
C30 C 1.1422(10) 1.2382(9) 0.8846(8) 0.0322(14) Uani 1 1 d . . . . .
C31 C 0.8272(10) 0.9420(9) 0.8662(8) 0.034(3) Uani 1 1 d . . . . .
H31 H 0.759141 0.949688 0.865207 0.041 Uiso 1 1 calc R U . . .
C32 C 0.8097(10) 0.8285(11) 0.8616(8) 0.036(3) Uani 1 1 d . . . . .
C33 C 0.8408(11) 0.6785(11) 0.8598(9) 0.041(3) Uani 1 1 d . . . . .
C34 C 0.7229(10) 0.6373(10) 0.8499(8) 0.0322(14) Uani 1 1 d . . . . .
H34 H 0.665378 0.558098 0.842892 0.039 Uiso 0.927(2) 1 calc R U P B 2
C35 C 0.6995(10) 0.7288(10) 0.8517(8) 0.034(3) Uani 1 1 d . . . . .
C36 C 1.0825(11) 1.3672(11) 0.8858(9) 0.039(2) Uani 1 1 d . . . . .
C37 C 1.2427(10) 1.3458(9) 0.8982(8) 0.0322(14) Uani 1 1 d . . . . .
C38 C 1.2017(10) 1.4244(10) 0.8995(8) 0.0322(14) Uani 1 1 d . . . . .
H38 H 1.249684 1.506107 0.908609 0.039 Uiso 0.073(2) 1 calc R U P B 1
C39 C 0.9976(10) 1.4115(10) 0.8800(9) 0.043(3) Uani 1 1 d . . . . .
H39A H 0.958720 1.401720 0.939220 0.065 Uiso 1 1 calc R U . . .
H39B H 0.939132 1.367905 0.820716 0.065 Uiso 1 1 calc R U . . .
H39C H 1.039391 1.493923 0.876370 0.065 Uiso 1 1 calc R U . . .
C40 C 0.9115(11) 0.6180(11) 0.8596(8) 0.040(3) Uani 1 1 d . . . . .
H40A H 0.869908 0.546889 0.885963 0.060 Uiso 1 1 calc R U . . .
H40B H 0.987256 0.669187 0.901214 0.060 Uiso 1 1 calc R U . . .
H40C H 0.923662 0.598364 0.791612 0.060 Uiso 1 1 calc R U . . .
C41 C 0.5852(10) 0.7228(10) 0.8444(9) 0.045(3) Uani 1 1 d . . . . .
H41A H 0.575633 0.756129 0.908931 0.068 Uiso 1 1 calc R U . . .
H41B H 0.523553 0.641639 0.824685 0.068 Uiso 1 1 calc R U . . .
H41C H 0.580144 0.766522 0.794676 0.068 Uiso 1 1 calc R U . . .
C42 C 1.3683(9) 1.3763(10) 0.9121(9) 0.040(3) Uani 1 1 d . . . . .
H42A H 1.389501 1.366716 0.978209 0.061 Uiso 1 1 calc R U . . .
H42B H 1.417202 1.457021 0.905440 0.061 Uiso 1 1 calc R U . . .
H42C H 1.380288 1.325111 0.861593 0.061 Uiso 1 1 calc R U . . .
B1 B 0.1821(13) -0.0574(14) 0.6031(10) 0.046(3) Uani 1 1 d . . . . .
B2 B 0.9212(13) 1.1568(13) 0.8687(10) 0.046(3) Uani 1 1 d . . . . .
Br1 Br 0.61372(13) 0.31895(13) 0.67548(13) 0.0459(7) Uani 0.826(4) 1 d . . P A
2
Br2 Br 1.29145(12) 1.58827(12) 0.92615(11) 0.0465(6) Uani 0.927(2) 1 d . . P B
2
F1 F 0.1710(6) -0.1053(6) 0.5116(6) 0.0547(11) Uani 1 1 d . . . . .
F2 F 0.1881(6) -0.1190(6) 0.6716(6) 0.0547(11) Uani 1 1 d . . . . .
F4 F 0.8547(6) 1.1428(6) 0.7888(6) 0.0547(11) Uani 1 1 d . . . . .
F5 F 0.8690(6) 1.1722(6) 0.9519(6) 0.0547(11) Uani 1 1 d . . . . .
N1 N 0.0017(9) 0.5773(9) 0.6281(7) 0.040(3) Uani 1 1 d . . . . .
N2 N 0.2781(8) 0.0720(8) 0.6299(7) 0.0353(11) Uani 1 1 d . . . . .
N3 N 0.0609(8) -0.0496(8) 0.6179(7) 0.0353(11) Uani 1 1 d . . . . .
N4 N 0.0487(8) 0.0485(8) 0.6232(7) 0.0353(11) Uani 1 1 d . . . . .
N5 N -0.1866(8) -0.0888(8) 0.6190(6) 0.035(2) Uani 1 1 d . . . . .
H5A H -0.140259 -0.013350 0.627413 0.042 Uiso 1 1 calc R U . . .
N6 N 1.5640(9) 0.9846(9) 0.8684(7) 0.0353(11) Uani 1 1 d . . . . .
N7 N 1.0285(8) 1.0289(8) 0.8762(7) 0.0353(11) Uani 1 1 d . . . . .
N8 N 0.9286(8) 1.0402(8) 0.8717(7) 0.0353(11) Uani 1 1 d . . . . .
N9 N 1.0456(7) 1.2523(7) 0.8782(7) 0.030(2) Uani 1 1 d . . . . .
N10 N 0.8942(9) 0.7967(9) 0.8653(7) 0.038(3) Uani 1 1 d . . . . .
H10 H 0.969799 0.843857 0.870407 0.045 Uiso 1 1 calc R U . . .
Br3 Br -0.4976(6) -0.3522(6) 0.5792(5) 0.037(3) Uani 0.174(4) 1 d . . P A 1
Br4 Br 0.6555(16) 0.4964(15) 0.8407(14) 0.0465(6) Uani 0.073(2) 1 d . . P B 1


_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
C1 C2 1.382(16) . ?
C1 C5 1.407(16) . ?
C1 C6 1.456(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.363(15) . ?
C3 H3 0.9500 . ?
C3 N1 1.324(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(16) . ?
C4 N1 1.329(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.205(15) . ?
C7 C8 1.418(16) . ?
C8 C9 1.394(15) . ?
C8 N4 1.330(14) . ?
C9 C10 1.399(16) . ?
C9 N2 1.396(14) . ?
C10 C11 1.378(16) . ?
C10 C13 1.518(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.416(16) . ?
C11 Br1 1.871(12) . ?
C12 C19 1.479(16) . ?
C12 N2 1.342(14) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 0.9500 . ?
C14 C15 1.375(15) . ?
C14 N3 1.340(14) . ?
C15 C16 1.404(16) . ?
C15 N5 1.398(14) . ?
C16 C17 1.364(16) . ?
C16 C20 1.512(16) . ?
C17 H17 0.9500 . ?
C17 C18 1.408(16) . ?
C17 Br3 1.766(14) . ?
C18 C21 1.474(15) . ?
C18 N5 1.356(14) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.421(16) . ?
C22 C26 1.374(16) . ?
C22 C27 1.451(18) . ?
C23 H23 1.06(11) . ?
C23 C24 1.357(17) . ?
C24 H24 1.01(12) . ?
C24 N6 1.342(15) . ?
C25 H25 0.86(12) . ?
C25 C26 1.365(17) . ?
C25 N6 1.319(15) . ?
C26 H26 0.97(11) . ?
C27 C28 1.217(16) . ?
C28 C29 1.417(18) . ?
C29 C30 1.427(15) . ?
C29 N7 1.309(14) . ?
C30 C37 1.391(15) . ?
C30 N9 1.374(13) . ?
C31 H31 0.9500 . ?
C31 C32 1.415(16) . ?
C31 N8 1.342(13) . ?
C32 C35 1.408(16) . ?
C32 N10 1.372(14) . ?
C33 C34 1.370(16) . ?
C33 C40 1.499(16) . ?
C33 N10 1.379(14) . ?
C34 H34 0.9500 . ?
C34 C35 1.397(15) . ?
C34 Br4 1.64(2) . ?
C35 C41 1.466(15) . ?
C36 C38 1.365(16) . ?
C36 C39 1.501(16) . ?
C36 N9 1.358(14) . ?
C37 C38 1.392(15) . ?
C37 C42 1.497(15) . ?
C38 H38 0.9500 . ?
C38 Br2 1.893(11) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
B1 F1 1.296(15) . ?
B1 F2 1.360(16) . ?
B1 N2 1.551(17) . ?
B1 N3 1.674(19) . ?
B2 F4 1.297(15) . ?
B2 F5 1.411(16) . ?
B2 N8 1.615(19) . ?
B2 N9 1.506(17) . ?
N3 N4 1.390(12) . ?
N5 H5A 0.8800 . ?
N7 N8 1.396(12) . ?
N10 H10 0.8800 . ?

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
C2 C1 C5 117.6(11) . . ?
C2 C1 C6 122.8(11) . . ?
C5 C1 C6 119.5(11) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.4(12) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 117.6 . . ?
N1 C3 C2 124.9(12) . . ?
N1 C3 H3 117.6 . . ?
C5 C4 H4 118.5 . . ?
N1 C4 H4 118.5 . . ?
N1 C4 C5 123.0(12) . . ?
C1 C5 H5 120.6 . . ?
C4 C5 C1 118.9(12) . . ?
C4 C5 H5 120.6 . . ?
C7 C6 C1 176.3(12) . . ?
C6 C7 C8 175.9(13) . . ?
C9 C8 C7 121.1(11) . . ?
N4 C8 C7 112.5(10) . . ?
N4 C8 C9 126.4(11) . . ?
C8 C9 C10 133.1(11) . . ?
C8 C9 N2 120.0(10) . . ?
N2 C9 C10 107.0(9) . . ?
C9 C10 C13 128.5(10) . . ?
C11 C10 C9 106.9(10) . . ?
C11 C10 C13 124.5(11) . . ?
C10 C11 H11 125.4 . . ?
C10 C11 C12 109.2(11) . . ?
C10 C11 Br1 128.8(10) . . ?
C12 C11 H11 125.4 . . ?
C12 C11 Br1 121.9(9) . . ?
C11 C12 C19 130.6(11) . . ?
N2 C12 C11 106.3(10) . . ?
N2 C12 C19 123.1(11) . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 H14 116.2 . . ?
N3 C14 H14 116.2 . . ?
N3 C14 C15 127.5(11) . . ?
C14 C15 C16 126.8(11) . . ?
C14 C15 N5 128.0(11) . . ?
N5 C15 C16 105.3(10) . . ?
C15 C16 C20 124.3(10) . . ?
C17 C16 C15 109.0(11) . . ?
C17 C16 C20 126.7(11) . . ?
C16 C17 H17 125.8 . . ?
C16 C17 C18 108.4(11) . . ?
C16 C17 Br3 135.2(10) . . ?
C18 C17 H17 125.8 . . ?
C18 C17 Br3 116.0(9) . . ?
C17 C18 C21 130.5(11) . . ?
N5 C18 C17 106.6(10) . . ?
N5 C18 C21 122.9(10) . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 122.7(11) . . ?
C26 C22 C23 117.7(11) . . ?
C26 C22 C27 119.6(11) . . ?
C22 C23 H23 109(6) . . ?
C24 C23 C22 117.3(12) . . ?
C24 C23 H23 134(6) . . ?
C23 C24 H24 110(7) . . ?
N6 C24 C23 125.5(12) . . ?
N6 C24 H24 124(7) . . ?
C26 C25 H25 121(8) . . ?
N6 C25 H25 113(8) . . ?
N6 C25 C26 125.3(12) . . ?
C22 C26 H26 120(6) . . ?
C25 C26 C22 118.9(12) . . ?
C25 C26 H26 121(6) . . ?
C28 C27 C22 178.0(13) . . ?
C27 C28 C29 174.1(13) . . ?
C28 C29 C30 120.3(10) . . ?
N7 C29 C28 113.1(10) . . ?
N7 C29 C30 126.6(10) . . ?
C37 C30 C29 131.0(10) . . ?
N9 C30 C29 119.3(10) . . ?
N9 C30 C37 109.6(9) . . ?
C32 C31 H31 116.2 . . ?
N8 C31 H31 116.2 . . ?
N8 C31 C32 127.6(11) . . ?
C35 C32 C31 124.2(11) . . ?
N10 C32 C31 126.8(11) . . ?
N10 C32 C35 109.0(10) . . ?
C34 C33 C40 131.8(11) . . ?
C34 C33 N10 107.4(10) . . ?
N10 C33 C40 120.6(11) . . ?
C33 C34 H34 124.9 . . ?
C33 C34 C35 110.1(10) . . ?
C33 C34 Br4 109.2(11) . . ?
C35 C34 H34 124.9 . . ?
C35 C34 Br4 140.7(12) . . ?
C32 C35 C41 127.4(11) . . ?
C34 C35 C32 104.9(10) . . ?
C34 C35 C41 127.7(11) . . ?
C38 C36 C39 131.0(11) . . ?
N9 C36 C38 107.6(10) . . ?
N9 C36 C39 121.4(11) . . ?
C30 C37 C38 104.4(10) . . ?
C30 C37 C42 129.9(10) . . ?
C38 C37 C42 125.7(10) . . ?
C36 C38 C37 110.3(10) . . ?
C36 C38 H38 124.9 . . ?
C36 C38 Br2 122.3(9) . . ?
C37 C38 H38 124.9 . . ?
C37 C38 Br2 127.2(9) . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C33 C40 H40A 109.5 . . ?
C33 C40 H40B 109.5 . . ?
C33 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C35 C41 H41A 109.5 . . ?
C35 C41 H41B 109.5 . . ?
C35 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C37 C42 H42A 109.5 . . ?
C37 C42 H42B 109.5 . . ?
C37 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
F1 B1 F2 115.1(14) . . ?
F1 B1 N2 113.8(11) . . ?
F1 B1 N3 107.6(10) . . ?
F2 B1 N2 112.5(10) . . ?
F2 B1 N3 104.1(10) . . ?
N2 B1 N3 102.1(11) . . ?
F4 B2 F5 108.9(13) . . ?
F4 B2 N8 110.0(11) . . ?
F4 B2 N9 114.9(11) . . ?
F5 B2 N8 105.8(10) . . ?
F5 B2 N9 111.4(10) . . ?
N9 B2 N8 105.5(11) . . ?
C3 N1 C4 117.1(10) . . ?
C9 N2 B1 125.9(10) . . ?
C12 N2 C9 110.6(9) . . ?
C12 N2 B1 123.3(10) . . ?
C14 N3 B1 115.6(10) . . ?
C14 N3 N4 117.1(9) . . ?
N4 N3 B1 126.8(9) . . ?
C8 N4 N3 116.8(9) . . ?
C15 N5 H5A 124.6 . . ?
C18 N5 C15 110.7(9) . . ?
C18 N5 H5A 124.6 . . ?
C25 N6 C24 115.3(10) . . ?
C29 N7 N8 115.7(9) . . ?
C31 N8 B2 116.7(9) . . ?
C31 N8 N7 115.9(9) . . ?
N7 N8 B2 127.4(9) . . ?
C30 N9 B2 125.4(10) . . ?
C36 N9 C30 108.1(9) . . ?
C36 N9 B2 126.4(11) . . ?
C32 N10 C33 108.5(10) . . ?
C32 N10 H10 125.8 . . ?
C33 N10 H10 125.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 N1 2.3(19) . . . . ?
C2 C1 C5 C4 2.6(17) . . . . ?
C2 C3 N1 C4 -0.4(18) . . . . ?
C5 C1 C2 C3 -3.3(17) . . . . ?
C5 C4 N1 C3 -0.3(17) . . . . ?
C6 C1 C2 C3 -178.0(11) . . . . ?
C6 C1 C5 C4 177.6(11) . . . . ?
C7 C8 C9 C10 3(2) . . . . ?
C7 C8 C9 N2 -177.3(10) . . . . ?
C7 C8 N4 N3 179.9(9) . . . . ?
C8 C9 C10 C11 179.2(13) . . . . ?
C8 C9 C10 C13 -3(2) . . . . ?
C8 C9 N2 C12 -179.9(11) . . . . ?
C8 C9 N2 B1 6.0(17) . . . . ?
C9 C8 N4 N3 -0.9(17) . . . . ?
C9 C10 C11 C12 0.7(14) . . . . ?
C9 C10 C11 Br1 -177.9(9) . . . . ?
C10 C9 N2 C12 -0.4(13) . . . . ?
C10 C9 N2 B1 -174.4(10) . . . . ?
C10 C11 C12 C19 177.2(12) . . . . ?
C10 C11 C12 N2 -0.9(14) . . . . ?
C11 C12 N2 C9 0.7(13) . . . . ?
C11 C12 N2 B1 175.0(10) . . . . ?
C13 C10 C11 C12 -176.8(11) . . . . ?
C13 C10 C11 Br1 4.6(18) . . . . ?
C14 C15 C16 C17 -178.8(12) . . . . ?
C14 C15 C16 C20 -1(2) . . . . ?
C14 C15 N5 C18 178.7(12) . . . . ?
C14 N3 N4 C8 177.9(10) . . . . ?
C15 C14 N3 B1 -172.7(11) . . . . ?
C15 C14 N3 N4 -0.5(17) . . . . ?
C15 C16 C17 C18 -0.7(14) . . . . ?
C15 C16 C17 Br3 172.0(11) . . . . ?
C16 C15 N5 C18 -1.3(13) . . . . ?
C16 C17 C18 C21 -177.5(12) . . . . ?
C16 C17 C18 N5 -0.1(13) . . . . ?
C17 C18 N5 C15 0.9(13) . . . . ?
C19 C12 N2 C9 -177.5(11) . . . . ?
C19 C12 N2 B1 -3.3(17) . . . . ?
C20 C16 C17 C18 -178.2(11) . . . . ?
C20 C16 C17 Br3 -5(2) . . . . ?
C21 C18 N5 C15 178.5(10) . . . . ?
C22 C23 C24 N6 -2.2(19) . . . . ?
C23 C22 C26 C25 0.5(17) . . . . ?
C23 C24 N6 C25 1.6(19) . . . . ?
C26 C22 C23 C24 1.0(17) . . . . ?
C26 C25 N6 C24 0.1(19) . . . . ?
C27 C22 C23 C24 -177.0(11) . . . . ?
C27 C22 C26 C25 178.5(11) . . . . ?
C28 C29 C30 C37 -5.2(19) . . . . ?
C28 C29 C30 N9 178.5(10) . . . . ?
C28 C29 N7 N8 -179.8(9) . . . . ?
C29 C30 C37 C38 -176.6(12) . . . . ?
C29 C30 C37 C42 2(2) . . . . ?
C29 C30 N9 C36 178.0(10) . . . . ?
C29 C30 N9 B2 0.4(17) . . . . ?
C29 N7 N8 C31 -179.9(10) . . . . ?
C29 N7 N8 B2 2.2(15) . . . . ?
C30 C29 N7 N8 0.7(17) . . . . ?
C30 C37 C38 C36 -1.0(13) . . . . ?
C30 C37 C38 Br2 174.4(8) . . . . ?
C31 C32 C35 C34 179.8(11) . . . . ?
C31 C32 C35 C41 0.0(19) . . . . ?
C31 C32 N10 C33 179.3(11) . . . . ?
C32 C31 N8 B2 176.1(11) . . . . ?
C32 C31 N8 N7 -2.0(16) . . . . ?
C33 C34 C35 C32 1.0(13) . . . . ?
C33 C34 C35 C41 -179.3(11) . . . . ?
C34 C33 N10 C32 1.6(13) . . . . ?
C35 C32 N10 C33 -1.0(13) . . . . ?
C37 C30 N9 C36 1.0(13) . . . . ?
C37 C30 N9 B2 -176.7(10) . . . . ?
C38 C36 N9 C30 -1.6(13) . . . . ?
C38 C36 N9 B2 176.1(10) . . . . ?
C39 C36 C38 C37 -179.1(12) . . . . ?
C39 C36 C38 Br2 5.2(19) . . . . ?
C39 C36 N9 C30 179.1(10) . . . . ?
C39 C36 N9 B2 -3.3(18) . . . . ?
C40 C33 C34 C35 -178.0(12) . . . . ?
C40 C33 C34 Br4 2.5(19) . . . . ?
C40 C33 N10 C32 178.5(10) . . . . ?
C42 C37 C38 C36 -179.2(11) . . . . ?
C42 C37 C38 Br2 -3.8(18) . . . . ?
B1 N3 N4 C8 -10.9(15) . . . . ?
Br1 C11 C12 C19 -4.1(19) . . . . ?
Br1 C11 C12 N2 177.8(8) . . . . ?
F1 B1 N2 C9 101.9(15) . . . . ?
F1 B1 N2 C12 -71.4(16) . . . . ?
F1 B1 N3 C14 68.0(13) . . . . ?
F1 B1 N3 N4 -103.3(13) . . . . ?
F2 B1 N2 C9 -124.8(13) . . . . ?
F2 B1 N2 C12 61.8(16) . . . . ?
F2 B1 N3 C14 -54.7(13) . . . . ?
F2 B1 N3 N4 134.0(11) . . . . ?
F4 B2 N8 C31 -56.8(14) . . . . ?
F4 B2 N8 N7 121.1(12) . . . . ?
F4 B2 N9 C30 -119.4(14) . . . . ?
F4 B2 N9 C36 63.4(17) . . . . ?
F5 B2 N8 C31 60.6(13) . . . . ?
F5 B2 N8 N7 -121.5(11) . . . . ?
F5 B2 N9 C30 116.2(13) . . . . ?
F5 B2 N9 C36 -61.0(16) . . . . ?
N1 C4 C5 C1 -0.9(18) . . . . ?
N2 C9 C10 C11 -0.2(13) . . . . ?
N2 C9 C10 C13 177.1(11) . . . . ?
N2 B1 N3 C14 -171.9(9) . . . . ?
N2 B1 N3 N4 16.7(14) . . . . ?
N3 C14 C15 C16 177.7(11) . . . . ?
N3 C14 C15 N5 -2(2) . . . . ?
N3 B1 N2 C9 -13.7(14) . . . . ?
N3 B1 N2 C12 172.9(10) . . . . ?
N4 C8 C9 C10 -175.8(12) . . . . ?
N4 C8 C9 N2 3.6(18) . . . . ?
N5 C15 C16 C17 1.2(13) . . . . ?
N5 C15 C16 C20 178.8(10) . . . . ?
N6 C25 C26 C22 -1(2) . . . . ?
N7 C29 C30 C37 174.3(12) . . . . ?
N7 C29 C30 N9 -2.0(18) . . . . ?
N8 C31 C32 C35 -177.2(11) . . . . ?
N8 C31 C32 N10 2.4(19) . . . . ?
N8 B2 N9 C30 1.8(15) . . . . ?
N8 B2 N9 C36 -175.4(10) . . . . ?
N9 C30 C37 C38 0.0(13) . . . . ?
N9 C30 C37 C42 178.1(11) . . . . ?
N9 C36 C38 C37 1.6(14) . . . . ?
N9 C36 C38 Br2 -174.0(8) . . . . ?
N9 B2 N8 C31 178.8(9) . . . . ?
N9 B2 N8 N7 -3.3(14) . . . . ?
N10 C32 C35 C34 0.1(13) . . . . ?
N10 C32 C35 C41 -179.7(11) . . . . ?
N10 C33 C34 C35 -1.6(14) . . . . ?
N10 C33 C34 Br4 178.8(11) . . . . ?
Br3 C17 C18 C21 8.2(17) . . . . ?
Br3 C17 C18 N5 -174.4(8) . . . . ?
Br4 C34 C35 C32 -179.7(16) . . . . ?
Br4 C34 C35 C41 0(3) . . . . ?

_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_bophy_alkyne_a
_database_code_depnum_ccdc_archive 'CCDC 2464600'
loop_
_audit_author_name
_audit_author_address
'Victor Victor Nemykin'
;University of Tennessee Knoxville
United States of America
;
_audit_update_record             
;
2025-06-16 deposited with the CCDC.	2025-10-16 downloaded from the CCDC.
;
_audit_creation_date             2025-06-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 B F2 N4 O'
_chemical_formula_sum            'C14 H15 B F2 N4 O'
_chemical_formula_weight         304.11
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        Pnma
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   16.4025(19)
_cell_length_b                   6.7909(8)
_cell_length_c                   12.6068(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1404.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3100
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.08
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5476
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1526 before and 0.0749 after correction.
The Ratio of minimum to maximum transmission is 0.7343.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.675
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.074
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15155
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.304
_diffrn_reflns_theta_min         2.483
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1430
_reflns_number_total             1874
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1874
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0676
_refine_ls_restrained_S_all      1.130
_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)+(0.0323P)²+1.9472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1383
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H8A(0.5) H8B(0.5) H8C(0.5) H9A(0.5) H9B(0.5) H9C(0.5) H14A(0.5)
 H14B(0.5) H14C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C11(H11), C13(H13), N1(H1)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C)
;
_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
C1 C 0.53890(18) 0.250000 0.3341(2) 0.0172(7) Uani 1 2 d S T P . .
C2 C 0.67491(19) 0.250000 0.3278(3) 0.0198(7) Uani 1 2 d S T P . .
C3 C 0.64537(19) 0.250000 0.2232(3) 0.0216(7) Uani 1 2 d S T P . .
H3 H 0.677942 0.250000 0.160849 0.026 Uiso 1 2 calc R U P . .
C4 C 0.56129(19) 0.250000 0.2258(2) 0.0196(7) Uani 1 2 d S T P . .
C5 C 0.45990(18) 0.250000 0.3737(2) 0.0168(7) Uani 1 2 d S T P . .
H5 H 0.418163 0.250000 0.321486 0.020 Uiso 1 2 calc R U P . .
C6 C 0.38466(18) 0.250000 0.6835(2) 0.0160(6) Uani 1 2 d S T P . .
C7 C 0.46841(18) 0.250000 0.6489(2) 0.0164(6) Uani 1 2 d S T P . .
H7 H 0.508836 0.250000 0.702850 0.020 Uiso 1 2 calc R U P . .
C8 C 0.76056(19) 0.250000 0.3669(3) 0.0260(8) Uani 1 2 d S T P . .
H8A H 0.779323 0.113943 0.375543 0.039 Uiso 0.5 1 calc R U P A -1
H8B H 0.763256 0.318248 0.435256 0.039 Uiso 0.5 1 calc R U P A -1
H8C H 0.795495 0.317809 0.315444 0.039 Uiso 0.5 1 calc R U P A -1
C9 C 0.5036(2) 0.250000 0.1331(2) 0.0266(8) Uani 1 2 d S T P . .
H9A H 0.466406 0.362483 0.138973 0.040 Uiso 0.5 1 calc R U P B -1
H9B H 0.472004 0.127468 0.133070 0.040 Uiso 0.5 1 calc R U P B -1
H9C H 0.534670 0.260049 0.066993 0.040 Uiso 0.5 1 calc R U P B -1
C10 C 0.25071(18) 0.250000 0.6642(2) 0.0165(6) Uani 1 2 d S T P . .
C11 C 0.26714(18) 0.250000 0.7728(2) 0.0171(7) Uani 1 2 d S T P . .
H11 H 0.227837 0.250000 0.828099 0.021 Uiso 1 2 calc R U P . .
C12 C 0.35148(19) 0.250000 0.7855(2) 0.0177(7) Uani 1 2 d S T P . .
C13 C 0.17288(19) 0.250000 0.6099(3) 0.0210(7) Uani 1 2 d S T P . .
H13 H 0.173648 0.250000 0.534536 0.025 Uiso 1 2 calc R U P . .
C14 C 0.3973(2) 0.250000 0.8888(2) 0.0264(8) Uani 1 2 d S T P . .
H14A H 0.454836 0.280208 0.875520 0.040 Uiso 0.5 1 calc R U P C -1
H14B H 0.392864 0.120007 0.922061 0.040 Uiso 0.5 1 calc R U P C -1
H14C H 0.374103 0.349784 0.936151 0.040 Uiso 0.5 1 calc R U P C -1
B1 B 0.3380(2) 0.250000 0.4904(3) 0.0170(8) Uani 1 2 d S T P . .
F1 F 0.30588(7) 0.4166(2) 0.44224(10) 0.0279(4) Uani 1 1 d . . . . .
N1 N 0.61089(15) 0.250000 0.3927(2) 0.0192(6) Uani 1 2 d S T P . .
H1 H 0.613634 0.250000 0.462442 0.023 Uiso 1 2 calc R U P . .
N2 N 0.43357(14) 0.250000 0.47374(19) 0.0152(6) Uani 1 2 d S T P . .
N3 N 0.32364(15) 0.250000 0.60975(19) 0.0151(6) Uani 1 2 d S T P . .
N4 N 0.49432(15) 0.250000 0.55137(19) 0.0172(6) Uani 1 2 d S T P . .
O1 O 0.10683(14) 0.250000 0.65314(19) 0.0319(7) 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
C1 C4 1.413(4) . ?
C1 C5 1.389(4) . ?
C1 N1 1.393(4) . ?
C2 C3 1.406(4) . ?
C2 C8 1.489(4) . ?
C2 N1 1.331(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(4) . ?
C4 C9 1.504(4) . ?
C5 H5 0.9500 . ?
C5 N2 1.333(4) . ?
C6 C7 1.441(4) . ?
C6 C12 1.397(4) . ?
C6 N3 1.366(4) . ?
C7 H7 0.9500 . ?
C7 N4 1.301(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.394(4) . ?
C10 C13 1.449(4) . ?
C10 N3 1.379(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(4) . ?
C12 C14 1.504(4) . ?
C13 H13 0.9500 . ?
C13 O1 1.213(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
B1 F1 1.388(2) 7_565 ?
B1 F1 1.388(2) . ?
B1 N2 1.581(4) . ?
B1 N3 1.523(4) . ?
N1 H1 0.8800 . ?
N2 N4 1.397(3) . ?

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
C5 C1 C4 126.2(3) . . ?
C5 C1 N1 126.8(3) . . ?
N1 C1 C4 107.0(3) . . ?
C3 C2 C8 129.5(3) . . ?
N1 C2 C3 107.8(3) . . ?
N1 C2 C8 122.8(3) . . ?
C2 C3 H3 125.6 . . ?
C4 C3 C2 108.8(3) . . ?
C4 C3 H3 125.6 . . ?
C1 C4 C9 125.9(3) . . ?
C3 C4 C1 106.5(3) . . ?
C3 C4 C9 127.6(3) . . ?
C1 C5 H5 115.0 . . ?
N2 C5 C1 130.0(3) . . ?
N2 C5 H5 115.0 . . ?
C12 C6 C7 130.5(3) . . ?
N3 C6 C7 119.5(3) . . ?
N3 C6 C12 109.9(3) . . ?
C6 C7 H7 116.7 . . ?
N4 C7 C6 126.7(3) . . ?
N4 C7 H7 116.7 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C13 129.4(3) . . ?
N3 C10 C11 108.7(3) . . ?
N3 C10 C13 121.9(3) . . ?
C10 C11 H11 126.1 . . ?
C12 C11 C10 107.8(3) . . ?
C12 C11 H11 126.1 . . ?
C6 C12 C14 127.1(3) . . ?
C11 C12 C6 106.3(3) . . ?
C11 C12 C14 126.6(3) . . ?
C10 C13 H13 117.5 . . ?
O1 C13 C10 125.1(3) . . ?
O1 C13 H13 117.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
F1 B1 F1 109.2(2) . 7_565 ?
F1 B1 N2 108.58(17) 7_565 . ?
F1 B1 N2 108.58(17) . . ?
F1 B1 N3 111.90(17) . . ?
F1 B1 N3 111.90(17) 7_565 . ?
N3 B1 N2 106.6(2) . . ?
C1 N1 H1 125.0 . . ?
C2 N1 C1 110.0(3) . . ?
C2 N1 H1 125.0 . . ?
C5 N2 B1 116.5(2) . . ?
C5 N2 N4 115.6(2) . . ?
N4 N2 B1 127.9(2) . . ?
C6 N3 C10 107.3(2) . . ?
C6 N3 B1 123.9(2) . . ?
C10 N3 B1 128.8(2) . . ?
C7 N4 N2 115.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C5 N2 B1 180.000(0) . . . . ?
C1 C5 N2 N4 0.000(0) . . . . ?
C2 C3 C4 C1 0.000(0) . . . . ?
C2 C3 C4 C9 180.000(0) . . . . ?
C3 C2 N1 C1 0.000(0) . . . . ?
C4 C1 C5 N2 180.000(0) . . . . ?
C4 C1 N1 C2 0.000(0) . . . . ?
C5 C1 C4 C3 180.000(0) . . . . ?
C5 C1 C4 C9 0.000(0) . . . . ?
C5 C1 N1 C2 180.000(0) . . . . ?
C5 N2 N4 C7 180.000(0) . . . . ?
C6 C7 N4 N2 0.000(1) . . . . ?
C7 C6 C12 C11 180.000(1) . . . . ?
C7 C6 C12 C14 0.000(1) . . . . ?
C7 C6 N3 C10 180.000(1) . . . . ?
C7 C6 N3 B1 0.000(1) . . . . ?
C8 C2 C3 C4 180.000(0) . . . . ?
C8 C2 N1 C1 180.000(0) . . . . ?
C10 C11 C12 C6 0.000(1) . . . . ?
C10 C11 C12 C14 180.000(1) . . . . ?
C11 C10 C13 O1 0.000(1) . . . . ?
C11 C10 N3 C6 0.000(1) . . . . ?
C11 C10 N3 B1 180.000(1) . . . . ?
C12 C6 C7 N4 180.000(1) . . . . ?
C12 C6 N3 C10 0.000(1) . . . . ?
C12 C6 N3 B1 180.000(1) . . . . ?
C13 C10 C11 C12 180.000(1) . . . . ?
C13 C10 N3 C6 180.000(1) . . . . ?
C13 C10 N3 B1 0.000(1) . . . . ?
B1 N2 N4 C7 0.000(0) . . . . ?
F1 B1 N2 C5 59.30(17) 7_565 . . . ?
F1 B1 N2 C5 -59.30(17) . . . . ?
F1 B1 N2 N4 120.70(17) . . . . ?
F1 B1 N2 N4 -120.70(17) 7_565 . . . ?
F1 B1 N3 C6 118.55(19) 7_565 . . . ?
F1 B1 N3 C6 -118.54(19) . . . . ?
F1 B1 N3 C10 61.46(19) . . . . ?
F1 B1 N3 C10 -61.45(19) 7_565 . . . ?
N1 C1 C4 C3 0.000(0) . . . . ?
N1 C1 C4 C9 180.000(0) . . . . ?
N1 C1 C5 N2 0.000(0) . . . . ?
N1 C2 C3 C4 0.000(0) . . . . ?
N2 B1 N3 C6 0.000(1) . . . . ?
N2 B1 N3 C10 180.000(1) . . . . ?
N3 C6 C7 N4 0.000(1) . . . . ?
N3 C6 C12 C11 0.000(1) . . . . ?
N3 C6 C12 C14 180.000(1) . . . . ?
N3 C10 C11 C12 0.000(1) . . . . ?
N3 C10 C13 O1 180.000(1) . . . . ?
N3 B1 N2 C5 180.000(0) . . . . ?
N3 B1 N2 N4 0.000(0) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
