# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_ic21850
_database_code_depnum_ccdc_archive 'CCDC 2248145'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung. Liu'
;Instrument Center, National Taiwan University
Taiwan
;
_audit_update_record             
;
2023-03-13 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H21 F N4'
_chemical_formula_weight         504.55

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   18.0446(6)
_cell_length_b                   11.8808(4)
_cell_length_c                   11.2129(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.5198(12)
_cell_angle_gamma                90
_cell_volume                     2396.39(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9866
_cell_measurement_theta_min      4.46
_cell_measurement_theta_max      77.83

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.711
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.9114
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28125
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.460
_diffrn_reflns_theta_max         78.124
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2508
_reflns_number_gt                2388
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0612P)²+1.9206P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2508
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1050
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.500000 0.80725(7) 0.750000 0.0235(2) Uani 1 2 d S T P . .
N1 N 0.42108(5) 0.45555(7) 0.57162(7) 0.0157(2) Uani 1 1 d . . . . .
N2 N 0.38287(5) 0.62648(7) 0.47104(8) 0.0159(2) Uani 1 1 d . . . . .
C1 C 0.32179(6) 0.33296(9) 0.41620(10) 0.0188(2) Uani 1 1 d . . . . .
H1A H 0.340873 0.298279 0.488556 0.023 Uiso 1 1 calc R U . . .
C2 C 0.27812(6) 0.27087(9) 0.33194(10) 0.0206(2) Uani 1 1 d . . . . .
H2A H 0.266862 0.194416 0.347536 0.025 Uiso 1 1 calc R U . . .
C3 C 0.25092(6) 0.32073(9) 0.22478(10) 0.0205(2) Uani 1 1 d . . . . .
H3A H 0.221813 0.278184 0.166628 0.025 Uiso 1 1 calc R U . . .
C4 C 0.26673(6) 0.43344(9) 0.20357(9) 0.0191(2) Uani 1 1 d . . . . .
H4A H 0.248333 0.467653 0.130577 0.023 Uiso 1 1 calc R U . . .
C5 C 0.30904(6) 0.49598(9) 0.28803(9) 0.0174(2) Uani 1 1 d . . . . .
H5A H 0.318675 0.573152 0.273369 0.021 Uiso 1 1 calc R U . . .
C6 C 0.33768(6) 0.44592(9) 0.39493(9) 0.0158(2) Uani 1 1 d . . . . .
C7 C 0.38393(6) 0.51129(9) 0.48576(9) 0.0151(2) Uani 1 1 d . . . . .
C8 C 0.46000(5) 0.51790(9) 0.65840(9) 0.0148(2) Uani 1 1 d . . . . .
C9 C 0.45926(5) 0.63869(9) 0.65619(8) 0.0147(2) Uani 1 1 d . . . . .
C10 C 0.500000 0.45988(12) 0.750000 0.0159(3) Uani 1 2 d S T P . .
H10A H 0.500001 0.379914 0.749999 0.019 Uiso 1 2 calc R U P . .
C11 C 0.500000 0.69444(12) 0.750000 0.0161(3) Uani 1 2 d S T P . .
C12 C 0.41828(5) 0.68923(9) 0.55364(9) 0.0149(2) Uani 1 1 d . . . . .
C13 C 0.41356(6) 0.81221(8) 0.52703(9) 0.0154(2) Uani 1 1 d . . . . .
C14 C 0.43835(6) 0.84895(9) 0.41879(9) 0.0179(2) Uani 1 1 d . . . . .
H14A H 0.459806 0.796827 0.367252 0.022 Uiso 1 1 calc R U . . .
C15 C 0.43174(6) 0.96153(9) 0.38627(10) 0.0204(2) Uani 1 1 d . . . . .
H15A H 0.449714 0.986484 0.313400 0.025 Uiso 1 1 calc R U . . .
C16 C 0.39903(6) 1.03754(9) 0.45968(10) 0.0206(2) Uani 1 1 d . . . . .
H16A H 0.395036 1.114625 0.437574 0.025 Uiso 1 1 calc R U . . .
C17 C 0.37210(6) 1.00100(9) 0.56554(10) 0.0199(2) Uani 1 1 d . . . . .
H17A H 0.348348 1.052701 0.614734 0.024 Uiso 1 1 calc R U . . .
C18 C 0.37980(6) 0.88872(9) 0.59986(9) 0.0185(2) Uani 1 1 d . . . . .
H18A H 0.362012 0.864213 0.673039 0.022 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C11 1.3404(17) . ?
N1 C7 1.3089(13) . ?
N1 C8 1.3716(13) . ?
N2 C12 1.3149(13) . ?
N2 C7 1.3783(13) . ?
C1 C2 1.3931(14) . ?
C1 C6 1.3967(15) . ?
C2 C3 1.3938(15) . ?
C3 C4 1.3935(16) . ?
C4 C5 1.3849(15) . ?
C5 C6 1.4000(14) . ?
C6 C7 1.4843(14) . ?
C8 C10 1.3909(12) . ?
C8 C9 1.4353(14) . ?
C9 C11 1.4013(12) . ?
C9 C12 1.4476(13) . ?
C12 C13 1.4923(14) . ?
C13 C18 1.3938(14) . ?
C13 C14 1.3963(14) . ?
C14 C15 1.3890(15) . ?
C15 C16 1.3850(16) . ?
C16 C17 1.3873(16) . ?
C17 C18 1.3923(15) . ?

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
C7 N1 C8 116.90(9) . . ?
C12 N2 C7 118.50(9) . . ?
C2 C1 C6 120.38(10) . . ?
C1 C2 C3 120.11(10) . . ?
C4 C3 C2 119.51(10) . . ?
C5 C4 C3 120.54(10) . . ?
C4 C5 C6 120.26(10) . . ?
C1 C6 C5 119.18(9) . . ?
C1 C6 C7 119.84(9) . . ?
C5 C6 C7 120.99(9) . . ?
N1 C7 N2 126.30(9) . . ?
N1 C7 C6 117.88(9) . . ?
N2 C7 C6 115.82(9) . . ?
N1 C8 C10 117.58(10) . . ?
N1 C8 C9 121.62(9) . . ?
C10 C8 C9 120.79(9) . . ?
C11 C9 C8 117.13(9) . . ?
C11 C9 C12 127.24(10) . . ?
C8 C9 C12 115.59(9) . . ?
C8 C10 C8 120.57(13) 2_656 . ?
F1 C11 C9 118.20(7) . . ?
F1 C11 C9 118.21(7) . 2_656 ?
C9 C11 C9 123.59(13) . 2_656 ?
N2 C12 C9 120.92(9) . . ?
N2 C12 C13 113.42(9) . . ?
C9 C12 C13 125.63(9) . . ?
C18 C13 C14 119.36(9) . . ?
C18 C13 C12 122.82(9) . . ?
C14 C13 C12 117.57(9) . . ?
C15 C14 C13 120.16(10) . . ?
C16 C15 C14 120.25(10) . . ?
C15 C16 C17 119.93(10) . . ?
C16 C17 C18 120.15(10) . . ?
C17 C18 C13 120.11(10) . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_ic21767
_database_code_depnum_ccdc_archive 'CCDC 2248146'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung. Liu'
;Instrument Center, National Taiwan University
Taiwan
;
_audit_update_record             
;
2023-03-13 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 Br F N2'
_chemical_formula_weight         379.23

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'
N N 0.0311 0.0180 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   4.1687(2)
_cell_length_b                   12.4116(7)
_cell_length_c                   15.8272(9)
_cell_angle_alpha                68.5349(18)
_cell_angle_beta                 85.512(2)
_cell_angle_gamma                81.5452(19)
_cell_volume                     753.56(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9966
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      74.40

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.835
_shelx_estimated_absorpt_T_min   0.447
_shelx_estimated_absorpt_T_max   0.831
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.7584
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11806
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.001
_diffrn_reflns_theta_max         74.430
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2948
_reflns_number_gt                2837
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0367P)²+1.0146P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2948
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0825
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.09782(6) 0.17568(2) 0.85531(2) 0.02185(10) Uani 1 1 d . . . . .
F1 F 0.9382(4) 0.56570(12) 0.90727(10) 0.0250(3) Uani 1 1 d . . . . .
N1 N 0.4006(5) 0.55209(17) 0.65379(13) 0.0188(4) Uani 1 1 d . . . . .
N2 N 0.3504(5) 0.73561(17) 0.67459(13) 0.0187(4) Uani 1 1 d . . . . .
C1 C 0.2986(6) 0.6649(2) 0.62925(16) 0.0183(5) Uani 1 1 d . . . . .
C2 C 0.5831(6) 0.5026(2) 0.72959(16) 0.0183(5) Uani 1 1 d . . . . .
C3 C 0.7116(6) 0.3841(2) 0.75283(16) 0.0201(5) Uani 1 1 d . . . . .
H3 H 0.664506 0.340917 0.717668 0.024 Uiso 1 1 calc R U . . .
C4 C 0.9044(6) 0.3323(2) 0.82649(16) 0.0196(5) Uani 1 1 d . . . . .
C5 C 0.9770(6) 0.3936(2) 0.88047(16) 0.0200(5) Uani 1 1 d . . . . .
H5 H 1.109891 0.356177 0.931858 0.024 Uiso 1 1 calc R U . . .
C6 C 0.8524(6) 0.5075(2) 0.85712(16) 0.0197(5) Uani 1 1 d . . . . .
C7 C 0.6496(6) 0.5683(2) 0.78183(16) 0.0179(5) Uani 1 1 d . . . . .
C8 C 0.5153(5) 0.6888(2) 0.75053(16) 0.0177(5) Uani 1 1 d . . . . .
C9 C 0.5524(6) 0.7695(2) 0.79832(16) 0.0185(5) Uani 1 1 d . . . . .
C10 C 0.4434(6) 0.7464(2) 0.88827(17) 0.0214(5) Uani 1 1 d . . . . .
H10 H 0.345255 0.677857 0.920328 0.026 Uiso 1 1 calc R U . . .
C11 C 0.4791(6) 0.8242(2) 0.93072(17) 0.0215(5) Uani 1 1 d . . . . .
H11 H 0.401299 0.809297 0.991468 0.026 Uiso 1 1 calc R U . . .
C12 C 0.6271(6) 0.9230(2) 0.88504(17) 0.0213(5) Uani 1 1 d . . . . .
H12 H 0.656049 0.974701 0.914873 0.026 Uiso 1 1 calc R U . . .
C13 C 0.7334(6) 0.9466(2) 0.79549(17) 0.0220(5) Uani 1 1 d . . . . .
H13 H 0.835532 1.014400 0.764201 0.026 Uiso 1 1 calc R U . . .
C14 C 0.6913(6) 0.8716(2) 0.75146(16) 0.0204(5) Uani 1 1 d . . . . .
H14 H 0.756885 0.889676 0.689471 0.024 Uiso 1 1 calc R U . . .
C15 C 0.1045(6) 0.7201(2) 0.54577(16) 0.0193(5) Uani 1 1 d . . . . .
C16 C -0.0056(6) 0.8391(2) 0.51323(17) 0.0221(5) Uani 1 1 d . . . . .
H16 H 0.042138 0.886605 0.544779 0.027 Uiso 1 1 calc R U . . .
C17 C -0.1854(6) 0.8887(2) 0.43464(17) 0.0247(5) Uani 1 1 d . . . . .
H17 H -0.259798 0.969948 0.412598 0.030 Uiso 1 1 calc R U . . .
C18 C -0.2559(6) 0.8196(2) 0.38855(17) 0.0249(5) Uani 1 1 d . . . . .
H18 H -0.379183 0.853542 0.335029 0.030 Uiso 1 1 calc R U . . .
C19 C -0.1474(6) 0.7015(2) 0.42017(17) 0.0244(5) Uani 1 1 d . . . . .
H19 H -0.197129 0.654289 0.388559 0.029 Uiso 1 1 calc R U . . .
C20 C 0.0344(6) 0.6515(2) 0.49827(17) 0.0221(5) Uani 1 1 d . . . . .
H20 H 0.111314 0.570470 0.519373 0.026 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.893(2) . ?
F1 C6 1.349(3) . ?
N1 C1 1.322(3) . ?
N1 C2 1.364(3) . ?
N2 C8 1.325(3) . ?
N2 C1 1.368(3) . ?
C1 C15 1.487(3) . ?
C2 C3 1.410(3) . ?
C2 C7 1.421(3) . ?
C3 C4 1.366(4) . ?
C4 C5 1.410(3) . ?
C5 C6 1.355(3) . ?
C6 C7 1.420(3) . ?
C7 C8 1.433(3) . ?
C8 C9 1.489(3) . ?
C9 C14 1.397(3) . ?
C9 C10 1.398(3) . ?
C10 C11 1.393(3) . ?
C11 C12 1.382(4) . ?
C12 C13 1.388(4) . ?
C13 C14 1.387(3) . ?
C15 C16 1.392(3) . ?
C15 C20 1.396(3) . ?
C16 C17 1.392(4) . ?
C17 C18 1.386(4) . ?
C18 C19 1.381(4) . ?
C19 C20 1.391(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 116.9(2) . . ?
C8 N2 C1 118.5(2) . . ?
N1 C1 N2 125.9(2) . . ?
N1 C1 C15 117.3(2) . . ?
N2 C1 C15 116.8(2) . . ?
N1 C2 C3 117.3(2) . . ?
N1 C2 C7 121.6(2) . . ?
C3 C2 C7 121.1(2) . . ?
C4 C3 C2 119.2(2) . . ?
C3 C4 C5 121.8(2) . . ?
C3 C4 Br1 119.96(18) . . ?
C5 C4 Br1 118.15(18) . . ?
C6 C5 C4 118.2(2) . . ?
F1 C6 C5 117.0(2) . . ?
F1 C6 C7 119.2(2) . . ?
C5 C6 C7 123.7(2) . . ?
C6 C7 C2 116.0(2) . . ?
C6 C7 C8 127.6(2) . . ?
C2 C7 C8 116.4(2) . . ?
N2 C8 C7 120.6(2) . . ?
N2 C8 C9 115.8(2) . . ?
C7 C8 C9 123.6(2) . . ?
C14 C9 C10 119.5(2) . . ?
C14 C9 C8 119.2(2) . . ?
C10 C9 C8 121.2(2) . . ?
C11 C10 C9 119.8(2) . . ?
C12 C11 C10 120.4(2) . . ?
C11 C12 C13 119.9(2) . . ?
C14 C13 C12 120.4(2) . . ?
C13 C14 C9 120.0(2) . . ?
C16 C15 C20 119.2(2) . . ?
C16 C15 C1 121.4(2) . . ?
C20 C15 C1 119.4(2) . . ?
C17 C16 C15 120.2(2) . . ?
C18 C17 C16 120.0(2) . . ?
C19 C18 C17 120.2(2) . . ?
C18 C19 C20 120.1(2) . . ?
C19 C20 C15 120.3(2) . . ?

_refine_diff_density_max         0.437
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.087

####################################################################### 
# 
# 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_ic21654
_database_code_depnum_ccdc_archive 'CCDC 2248147'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung. Liu'
;Instrument Center, National Taiwan University
Taiwan
;
_audit_update_record             
;
2023-03-13 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 Br F N2'
_chemical_formula_weight         379.23

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'
N N 0.0311 0.0180 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   7.3882(2)
_cell_length_b                   9.8687(3)
_cell_length_c                   21.9346(6)
_cell_angle_alpha                93.6965(6)
_cell_angle_beta                 93.9425(6)
_cell_angle_gamma                101.9771(6)
_cell_volume                     1555.69(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9874
_cell_measurement_theta_min      4.05
_cell_measurement_theta_max      78.60

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.715
_shelx_estimated_absorpt_T_min   0.356
_shelx_estimated_absorpt_T_max   0.708
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6943
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23763
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.025
_diffrn_reflns_theta_max         79.111
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6441
_reflns_number_gt                6299
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+1.5260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6441
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0758
_refine_ls_wR_factor_gt          0.0751
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.72378(2) 0.60614(2) -0.11327(2) 0.01592(6) Uani 1 1 d . . . . .
F1 F 0.52266(16) 0.13028(11) 0.04312(5) 0.0191(2) Uani 1 1 d . . . . .
N1 N 0.8421(2) 0.59818(15) 0.02092(7) 0.0120(3) Uani 1 1 d . . . . .
N2 N 0.8590(2) 0.51403(15) 0.12048(7) 0.0126(3) Uani 1 1 d . . . . .
C1 C 0.7351(2) 0.47430(17) -0.00137(8) 0.0113(3) Uani 1 1 d . . . . .
C2 C 0.6631(2) 0.45610(19) -0.06382(8) 0.0137(3) Uani 1 1 d . . . . .
C3 C 0.5520(2) 0.33345(19) -0.08816(8) 0.0158(3) Uani 1 1 d . . . . .
H3 H 0.505869 0.323481 -0.130077 0.019 Uiso 1 1 calc R U . . .
C4 C 0.5059(2) 0.22211(19) -0.05134(8) 0.0163(3) Uani 1 1 d . . . . .
H4 H 0.428164 0.136846 -0.068023 0.020 Uiso 1 1 calc R U . . .
C5 C 0.5742(2) 0.23795(18) 0.00877(8) 0.0142(3) Uani 1 1 d . . . . .
C6 C 0.6915(2) 0.36124(18) 0.03626(8) 0.0117(3) Uani 1 1 d . . . . .
C7 C 0.7646(2) 0.38960(17) 0.09932(8) 0.0119(3) Uani 1 1 d . . . . .
C8 C 0.7434(2) 0.28391(18) 0.14538(8) 0.0128(3) Uani 1 1 d . . . . .
C9 C 0.8021(3) 0.15940(19) 0.13550(9) 0.0162(3) Uani 1 1 d . . . . .
H9 H 0.851949 0.138787 0.098064 0.019 Uiso 1 1 calc R U . . .
C10 C 0.7876(3) 0.0652(2) 0.18046(9) 0.0189(4) Uani 1 1 d . . . . .
H10 H 0.829016 -0.019029 0.173834 0.023 Uiso 1 1 calc R U . . .
C11 C 0.7128(3) 0.0942(2) 0.23501(9) 0.0187(4) Uani 1 1 d . . . . .
H11 H 0.699734 0.028545 0.265083 0.022 Uiso 1 1 calc R U . . .
C12 C 0.6571(3) 0.2193(2) 0.24560(8) 0.0177(4) Uani 1 1 d . . . . .
H12 H 0.607800 0.239838 0.283150 0.021 Uiso 1 1 calc R U . . .
C13 C 0.6737(2) 0.31398(19) 0.20124(8) 0.0148(3) Uani 1 1 d . . . . .
H13 H 0.637500 0.400022 0.208821 0.018 Uiso 1 1 calc R U . . .
C14 C 0.8967(2) 0.61361(18) 0.07986(8) 0.0118(3) Uani 1 1 d . . . . .
C15 C 1.0141(2) 0.74935(18) 0.10413(8) 0.0129(3) Uani 1 1 d . . . . .
C16 C 1.1073(3) 0.76642(19) 0.16273(8) 0.0157(3) Uani 1 1 d . . . . .
H16 H 1.091408 0.691278 0.188219 0.019 Uiso 1 1 calc R U . . .
C17 C 1.2230(3) 0.8928(2) 0.18378(9) 0.0192(4) Uani 1 1 d . . . . .
H17 H 1.285354 0.903760 0.223717 0.023 Uiso 1 1 calc R U . . .
C18 C 1.2483(3) 1.00322(19) 0.14684(9) 0.0191(4) Uani 1 1 d . . . . .
H18 H 1.328557 1.089227 0.161213 0.023 Uiso 1 1 calc R U . . .
C19 C 1.1551(3) 0.98701(19) 0.08862(9) 0.0181(4) Uani 1 1 d . . . . .
H19 H 1.171674 1.062442 0.063298 0.022 Uiso 1 1 calc R U . . .
C20 C 1.0384(2) 0.86154(19) 0.06732(8) 0.0152(3) Uani 1 1 d . . . . .
H20 H 0.974675 0.851610 0.027637 0.018 Uiso 1 1 calc R U . . .
Br2 Br 0.22820(3) -0.24686(2) 0.56200(2) 0.01727(6) Uani 1 1 d . . . . .
F2 F 0.38161(16) 0.03243(11) 0.33067(5) 0.0202(2) Uani 1 1 d . . . . .
N3 N 0.2136(2) 0.04905(15) 0.53854(7) 0.0117(3) Uani 1 1 d . . . . .
N4 N 0.2372(2) 0.25638(15) 0.48622(7) 0.0121(3) Uani 1 1 d . . . . .
C21 C 0.2548(2) -0.01807(17) 0.48721(8) 0.0112(3) Uani 1 1 d . . . . .
C22 C 0.2701(2) -0.15933(18) 0.48880(8) 0.0139(3) Uani 1 1 d . . . . .
C23 C 0.3146(2) -0.23074(18) 0.43849(9) 0.0166(3) Uani 1 1 d . . . . .
H23 H 0.321850 -0.325446 0.440076 0.020 Uiso 1 1 calc R U . . .
C24 C 0.3495(3) -0.16451(19) 0.38453(9) 0.0175(4) Uani 1 1 d . . . . .
H24 H 0.381369 -0.213849 0.349650 0.021 Uiso 1 1 calc R U . . .
C25 C 0.3374(2) -0.02929(18) 0.38243(8) 0.0137(3) Uani 1 1 d . . . . .
C26 C 0.2849(2) 0.04881(18) 0.43206(8) 0.0118(3) Uani 1 1 d . . . . .
C27 C 0.2673(2) 0.19082(18) 0.43434(8) 0.0116(3) Uani 1 1 d . . . . .
C28 C 0.2780(2) 0.27546(18) 0.38046(8) 0.0123(3) Uani 1 1 d . . . . .
C29 C 0.1645(2) 0.23043(19) 0.32634(8) 0.0153(3) Uani 1 1 d . . . . .
H29 H 0.080724 0.142612 0.322966 0.018 Uiso 1 1 calc R U . . .
C30 C 0.1737(3) 0.3136(2) 0.27737(8) 0.0176(4) Uani 1 1 d . . . . .
H30 H 0.094661 0.283450 0.240903 0.021 Uiso 1 1 calc R U . . .
C31 C 0.2987(3) 0.44104(19) 0.28184(8) 0.0160(3) Uani 1 1 d . . . . .
H31 H 0.306450 0.497184 0.248132 0.019 Uiso 1 1 calc R U . . .
C32 C 0.4122(2) 0.48642(18) 0.33545(8) 0.0150(3) Uani 1 1 d . . . . .
H32 H 0.498593 0.572993 0.338194 0.018 Uiso 1 1 calc R U . . .
C33 C 0.3997(2) 0.40525(18) 0.38512(8) 0.0136(3) Uani 1 1 d . . . . .
H33 H 0.473976 0.438115 0.422306 0.016 Uiso 1 1 calc R U . . .
C34 C 0.2109(2) 0.18167(18) 0.53623(8) 0.0112(3) Uani 1 1 d . . . . .
C35 C 0.1708(2) 0.25593(17) 0.59288(8) 0.0122(3) Uani 1 1 d . . . . .
C36 C 0.1740(3) 0.19356(19) 0.64829(8) 0.0156(3) Uani 1 1 d . . . . .
H36 H 0.203107 0.104346 0.649446 0.019 Uiso 1 1 calc R U . . .
C37 C 0.1349(3) 0.2616(2) 0.70166(8) 0.0188(4) Uani 1 1 d . . . . .
H37 H 0.138822 0.219419 0.739315 0.023 Uiso 1 1 calc R U . . .
C38 C 0.0900(3) 0.3915(2) 0.69999(8) 0.0180(4) Uani 1 1 d . . . . .
H38 H 0.062839 0.437866 0.736462 0.022 Uiso 1 1 calc R U . . .
C39 C 0.0850(3) 0.45355(19) 0.64491(8) 0.0163(3) Uani 1 1 d . . . . .
H39 H 0.052963 0.541770 0.643750 0.020 Uiso 1 1 calc R U . . .
C40 C 0.1268(2) 0.38683(18) 0.59149(8) 0.0139(3) Uani 1 1 d . . . . .
H40 H 0.125506 0.430257 0.554097 0.017 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.8891(18) . ?
F1 C5 1.348(2) . ?
N1 C14 1.317(2) . ?
N1 C1 1.352(2) . ?
N2 C7 1.318(2) . ?
N2 C14 1.368(2) . ?
C1 C2 1.421(2) . ?
C1 C6 1.427(2) . ?
C2 C3 1.367(3) . ?
C3 C4 1.404(3) . ?
C4 C5 1.366(3) . ?
C5 C6 1.411(2) . ?
C6 C7 1.438(2) . ?
C7 C8 1.491(2) . ?
C8 C9 1.395(2) . ?
C8 C13 1.399(2) . ?
C9 C10 1.392(3) . ?
C10 C11 1.390(3) . ?
C11 C12 1.391(3) . ?
C12 C13 1.386(3) . ?
C14 C15 1.481(2) . ?
C15 C16 1.399(2) . ?
C15 C20 1.401(2) . ?
C16 C17 1.388(3) . ?
C17 C18 1.389(3) . ?
C18 C19 1.392(3) . ?
C19 C20 1.386(3) . ?
Br2 C22 1.8857(18) . ?
F2 C25 1.351(2) . ?
N3 C34 1.317(2) . ?
N3 C21 1.354(2) . ?
N4 C27 1.327(2) . ?
N4 C34 1.363(2) . ?
C21 C26 1.424(2) . ?
C21 C22 1.424(2) . ?
C22 C23 1.367(3) . ?
C23 C24 1.402(3) . ?
C24 C25 1.359(3) . ?
C25 C26 1.415(2) . ?
C26 C27 1.432(2) . ?
C27 C28 1.488(2) . ?
C28 C29 1.396(2) . ?
C28 C33 1.397(2) . ?
C29 C30 1.390(3) . ?
C30 C31 1.391(3) . ?
C31 C32 1.388(3) . ?
C32 C33 1.390(2) . ?
C34 C35 1.480(2) . ?
C35 C40 1.398(2) . ?
C35 C36 1.398(2) . ?
C36 C37 1.390(3) . ?
C37 C38 1.391(3) . ?
C38 C39 1.391(3) . ?
C39 C40 1.392(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
C14 N1 C1 117.39(15) . . ?
C7 N2 C14 118.12(15) . . ?
N1 C1 C2 119.26(16) . . ?
N1 C1 C6 121.73(15) . . ?
C2 C1 C6 119.01(15) . . ?
C3 C2 C1 121.37(17) . . ?
C3 C2 Br1 120.09(14) . . ?
C1 C2 Br1 118.54(13) . . ?
C2 C3 C4 120.14(17) . . ?
C5 C4 C3 119.18(17) . . ?
F1 C5 C4 117.49(16) . . ?
F1 C5 C6 119.21(16) . . ?
C4 C5 C6 123.29(17) . . ?
C5 C6 C1 117.00(16) . . ?
C5 C6 C7 127.38(16) . . ?
C1 C6 C7 115.51(15) . . ?
N2 C7 C6 121.24(16) . . ?
N2 C7 C8 114.76(15) . . ?
C6 C7 C8 124.00(15) . . ?
C9 C8 C13 119.28(16) . . ?
C9 C8 C7 121.34(16) . . ?
C13 C8 C7 119.26(15) . . ?
C10 C9 C8 120.04(17) . . ?
C11 C10 C9 120.19(17) . . ?
C10 C11 C12 120.04(17) . . ?
C13 C12 C11 119.84(17) . . ?
C12 C13 C8 120.57(17) . . ?
N1 C14 N2 125.81(16) . . ?
N1 C14 C15 117.28(15) . . ?
N2 C14 C15 116.89(15) . . ?
C16 C15 C20 119.09(16) . . ?
C16 C15 C14 121.00(16) . . ?
C20 C15 C14 119.87(16) . . ?
C17 C16 C15 120.24(17) . . ?
C16 C17 C18 120.44(18) . . ?
C17 C18 C19 119.55(17) . . ?
C20 C19 C18 120.46(18) . . ?
C19 C20 C15 120.22(17) . . ?
C34 N3 C21 116.97(15) . . ?
C27 N4 C34 117.90(15) . . ?
N3 C21 C26 121.94(15) . . ?
N3 C21 C22 118.83(16) . . ?
C26 C21 C22 119.22(15) . . ?
C23 C22 C21 121.00(17) . . ?
C23 C22 Br2 120.27(14) . . ?
C21 C22 Br2 118.73(13) . . ?
C22 C23 C24 120.14(17) . . ?
C25 C24 C23 119.61(16) . . ?
F2 C25 C24 117.59(16) . . ?
F2 C25 C26 119.37(15) . . ?
C24 C25 C26 123.03(17) . . ?
C25 C26 C21 116.90(16) . . ?
C25 C26 C27 127.32(16) . . ?
C21 C26 C27 115.70(15) . . ?
N4 C27 C26 121.06(16) . . ?
N4 C27 C28 114.86(15) . . ?
C26 C27 C28 124.08(15) . . ?
C29 C28 C33 119.42(16) . . ?
C29 C28 C27 121.53(16) . . ?
C33 C28 C27 119.00(15) . . ?
C30 C29 C28 120.25(17) . . ?
C29 C30 C31 119.92(17) . . ?
C32 C31 C30 120.16(17) . . ?
C31 C32 C33 120.05(17) . . ?
C32 C33 C28 120.15(16) . . ?
N3 C34 N4 126.20(16) . . ?
N3 C34 C35 116.95(15) . . ?
N4 C34 C35 116.83(15) . . ?
C40 C35 C36 119.53(16) . . ?
C40 C35 C34 120.78(16) . . ?
C36 C35 C34 119.68(15) . . ?
C37 C36 C35 120.23(17) . . ?
C36 C37 C38 120.04(17) . . ?
C39 C38 C37 119.97(17) . . ?
C38 C39 C40 120.24(17) . . ?
C39 C40 C35 119.97(17) . . ?

_refine_diff_density_max         0.898
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_ic21665
_database_code_depnum_ccdc_archive 'CCDC 2248148'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung. Liu'
;Instrument Center, National Taiwan University
Taiwan
;
_audit_update_record             
;
2023-03-22 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        6-Bromo-5-fluoro-2,4-diphenylquinazoline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 Br F N2'
_chemical_formula_weight         379.23

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'
N N 0.0311 0.0180 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   16.4004(10)
_cell_length_b                   4.9641(3)
_cell_length_c                   19.8649(12)
_cell_angle_alpha                90
_cell_angle_beta                 107.5625(18)
_cell_angle_gamma                90
_cell_volume                     1541.88(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9173
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      78.08

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.749
_shelx_estimated_absorpt_T_min   0.316
_shelx_estimated_absorpt_T_max   0.835
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.7660
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28264
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.826
_diffrn_reflns_theta_max         78.665
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3206
_reflns_number_gt                3128
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+7.7823P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3206
_refine_ls_number_parameters     248
_refine_ls_number_restraints     390
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.79803(2) 1.31735(7) 0.85685(2) 0.01965(12) Uani 1 1 d . . . . .
F1 F 0.67115(13) 0.9899(5) 0.74777(11) 0.0295(5) Uani 1 1 d . . . . .
N1 N 0.86836(17) 0.4614(6) 0.66608(14) 0.0139(5) Uani 1 1 d . . . . .
N2 N 0.71906(17) 0.3791(6) 0.61289(14) 0.0161(6) Uani 1 1 d . . . . .
C1 C 0.7507(2) 0.9225(7) 0.74843(18) 0.0179(7) Uani 1 1 d . . . . .
C2 C 0.8174(2) 1.0505(7) 0.79521(17) 0.0164(7) Uani 1 1 d . . . . .
C3 C 0.9022(2) 0.9865(7) 0.79877(18) 0.0172(7) Uani 1 1 d . . . . .
H3 H 0.948609 1.078305 0.831011 0.021 Uiso 1 1 calc R U . . .
C4 C 0.9174(2) 0.7915(7) 0.75560(17) 0.0157(7) Uani 1 1 d . . . . .
H4 H 0.974541 0.747319 0.758058 0.019 Uiso 1 1 calc R U . . .
C5 C 0.8487(2) 0.6546(7) 0.70721(17) 0.0141(6) Uani 1 1 d . . . . .
C6 C 0.7624(2) 0.7186(7) 0.70241(17) 0.0154(7) Uani 1 1 d . . . . .
C7 C 0.6977(2) 0.5681(7) 0.65145(17) 0.0151(6) Uani 1 1 d . . . . .
C8 C 0.8040(2) 0.3328(7) 0.62129(17) 0.0136(6) Uani 1 1 d . . . . .
C9 C 0.8242(2) 0.1205(7) 0.57651(16) 0.0136(6) Uani 1 1 d . . . . .
C10 C 0.7600(2) -0.0296(7) 0.52923(17) 0.0168(7) Uani 1 1 d . . . . .
H10 H 0.701750 0.007007 0.524834 0.020 Uiso 1 1 calc R U . . .
C11 C 0.7801(2) -0.2315(7) 0.48854(18) 0.0196(7) Uani 1 1 d . . . . .
H11 H 0.735874 -0.333171 0.456795 0.024 Uiso 1 1 calc R U . . .
C12 C 0.8651(2) -0.2842(7) 0.49444(18) 0.0198(7) Uani 1 1 d . . . . .
H12 H 0.878957 -0.421270 0.466373 0.024 Uiso 1 1 calc R U . . .
C13 C 0.9296(2) -0.1380(7) 0.54098(17) 0.0168(7) Uani 1 1 d . . . . .
H13 H 0.987671 -0.176885 0.545247 0.020 Uiso 1 1 calc R U . . .
C14 C 0.9099(2) 0.0659(7) 0.58163(17) 0.0149(6) Uani 1 1 d . . . . .
H14 H 0.954490 0.168226 0.612834 0.018 Uiso 1 1 calc R U . . .
C15 C 0.6065(2) 0.6038(12) 0.6418(2) 0.0175(14) Uani 0.499(4) 1 d G U P A 1
C16 C 0.5705(3) 0.5904(11) 0.69675(19) 0.0223(12) Uani 0.499(4) 1 d G U P A 1
H16A H 0.605891 0.560165 0.743697 0.027 Uiso 0.499(4) 1 calc R U P A 1
C17 C 0.4828(3) 0.6214(12) 0.6830(2) 0.0261(13) Uani 0.499(4) 1 d G U P A 1
H17A H 0.458165 0.612306 0.720513 0.031 Uiso 0.499(4) 1 calc R U P A 1
C18 C 0.4310(2) 0.6657(13) 0.6143(3) 0.0249(14) Uani 0.499(4) 1 d G U P A 1
H18A H 0.371037 0.686900 0.604865 0.030 Uiso 0.499(4) 1 calc R U P A 1
C19 C 0.4670(3) 0.6791(12) 0.5594(2) 0.0256(13) Uani 0.499(4) 1 d G U P A 1
H19A H 0.431636 0.709354 0.512402 0.031 Uiso 0.499(4) 1 calc R U P A 1
C20 C 0.5548(3) 0.6481(11) 0.5731(2) 0.0208(12) Uani 0.499(4) 1 d G U P A 1
H20A H 0.579362 0.657214 0.535585 0.025 Uiso 0.499(4) 1 calc R U P A 1
C15' C 0.6012(2) 0.6139(10) 0.6312(3) 0.0180(14) Uani 0.501(4) 1 d G U P A 2
C16' C 0.5679(3) 0.8693(8) 0.6112(3) 0.0206(12) Uani 0.501(4) 1 d G U P A 2
H16B H 0.604881 1.013301 0.608408 0.025 Uiso 0.501(4) 1 calc R U P A 2
C17' C 0.4805(3) 0.9140(8) 0.5953(3) 0.0218(12) Uani 0.501(4) 1 d G U P A 2
H17B H 0.457686 1.088513 0.581689 0.026 Uiso 0.501(4) 1 calc R U P A 2
C18' C 0.4263(2) 0.7033(10) 0.5994(3) 0.0230(14) Uani 0.501(4) 1 d G U P A 2
H18B H 0.366566 0.733801 0.588563 0.028 Uiso 0.501(4) 1 calc R U P A 2
C19' C 0.4596(3) 0.4479(8) 0.6194(3) 0.0242(13) Uani 0.501(4) 1 d G U P A 2
H19B H 0.422641 0.303872 0.622156 0.029 Uiso 0.501(4) 1 calc R U P A 2
C20' C 0.5471(3) 0.4032(8) 0.6352(3) 0.0222(12) Uani 0.501(4) 1 d G U P A 2
H20B H 0.569836 0.228654 0.648876 0.027 Uiso 0.501(4) 1 calc R U P A 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.895(3) . ?
F1 C1 1.343(4) . ?
N1 C8 1.321(4) . ?
N1 C5 1.361(4) . ?
N2 C7 1.323(4) . ?
N2 C8 1.372(4) . ?
C1 C2 1.361(5) . ?
C1 C6 1.415(5) . ?
C2 C3 1.407(5) . ?
C3 C4 1.365(5) . ?
C4 C5 1.415(5) . ?
C5 C6 1.424(4) . ?
C6 C7 1.436(5) . ?
C7 C15 1.460(4) . ?
C7 C15' 1.528(4) . ?
C8 C9 1.480(5) . ?
C9 C10 1.396(5) . ?
C9 C14 1.405(4) . ?
C10 C11 1.388(5) . ?
C11 C12 1.388(5) . ?
C12 C13 1.382(5) . ?
C13 C14 1.392(5) . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C18 C19 1.3900 . ?
C19 C20 1.3900 . ?
C15' C16' 1.3900 . ?
C15' C20' 1.3900 . ?
C16' C17' 1.3900 . ?
C17' C18' 1.3900 . ?
C18' C19' 1.3900 . ?
C19' C20' 1.3900 . ?

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
C8 N1 C5 117.3(3) . . ?
C7 N2 C8 119.0(3) . . ?
F1 C1 C2 118.0(3) . . ?
F1 C1 C6 119.5(3) . . ?
C2 C1 C6 122.5(3) . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 Br1 120.7(3) . . ?
C3 C2 Br1 118.8(3) . . ?
C4 C3 C2 119.5(3) . . ?
C3 C4 C5 120.6(3) . . ?
N1 C5 C4 117.5(3) . . ?
N1 C5 C6 121.9(3) . . ?
C4 C5 C6 120.6(3) . . ?
C1 C6 C5 116.2(3) . . ?
C1 C6 C7 127.7(3) . . ?
C5 C6 C7 116.0(3) . . ?
N2 C7 C6 120.6(3) . . ?
N2 C7 C15 116.7(3) . . ?
C6 C7 C15 122.6(3) . . ?
N2 C7 C15' 112.8(3) . . ?
C6 C7 C15' 126.5(3) . . ?
N1 C8 N2 125.2(3) . . ?
N1 C8 C9 118.1(3) . . ?
N2 C8 C9 116.7(3) . . ?
C10 C9 C14 118.8(3) . . ?
C10 C9 C8 121.6(3) . . ?
C14 C9 C8 119.6(3) . . ?
C11 C10 C9 120.9(3) . . ?
C12 C11 C10 119.7(3) . . ?
C13 C12 C11 120.3(3) . . ?
C12 C13 C14 120.3(3) . . ?
C13 C14 C9 120.0(3) . . ?
C16 C15 C20 120.0 . . ?
C16 C15 C7 123.5(3) . . ?
C20 C15 C7 116.5(3) . . ?
C17 C16 C15 120.0 . . ?
C16 C17 C18 120.0 . . ?
C17 C18 C19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C19 C20 C15 120.0 . . ?
C16' C15' C20' 120.0 . . ?
C16' C15' C7 119.9(3) . . ?
C20' C15' C7 120.1(3) . . ?
C17' C16' C15' 120.0 . . ?
C16' C17' C18' 120.0 . . ?
C19' C18' C17' 120.0 . . ?
C18' C19' C20' 120.0 . . ?
C19' C20' C15' 120.0 . . ?

_refine_diff_density_max         0.591
_refine_diff_density_min         -0.980
_refine_diff_density_rms         0.101

####################################################################### 
# 
# 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_ic21646_sq
_database_code_depnum_ccdc_archive 'CCDC 2248149'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung. Liu'
;Instrument Center, National Taiwan University
Taiwan
;
_audit_update_record             
;
2023-03-13 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C61 H37 F2 N7'
_chemical_formula_weight         905.97

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'
N N 0.0311 0.0180 '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'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   11.6106(2)
_cell_length_b                   13.7588(3)
_cell_length_c                   17.4536(4)
_cell_angle_alpha                109.3869(8)
_cell_angle_beta                 98.5209(8)
_cell_angle_gamma                93.7331(8)
_cell_volume                     2581.46(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      78.03

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_F_000             940
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.598
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.9228
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47577
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.729
_diffrn_reflns_theta_max         78.516
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             10499
_reflns_number_gt                9669
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 Structure factors included contributions from the .fab file. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+1.2139P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10499
_refine_ls_number_parameters     631
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.28321(6) 0.42567(5) 0.13782(4) 0.02261(15) Uani 1 1 d . . . . .
F2 F 0.75056(6) 0.78130(5) 0.24240(4) 0.02391(16) Uani 1 1 d . . . . .
N1 N 0.31506(9) 0.10350(8) 0.07057(6) 0.0212(2) Uani 1 1 d . . . . .
N2 N 0.50823(9) 0.14912(8) 0.15167(6) 0.0205(2) Uani 1 1 d . . . . .
N3 N 0.57302(9) 0.64042(8) 0.26233(6) 0.0201(2) Uani 1 1 d . . . . .
N4 N 0.66900(8) 0.50497(7) 0.29350(6) 0.0188(2) Uani 1 1 d . . . . .
N5 N 0.81593(9) 0.57250(8) 0.41267(6) 0.0226(2) Uani 1 1 d . . . . .
N6 N 1.09002(8) 0.86370(8) 0.45748(6) 0.0194(2) Uani 1 1 d . . . . .
N7 N 1.05274(9) 0.98649(8) 0.38996(6) 0.0199(2) Uani 1 1 d . . . . .
C1 C 0.43490(10) -0.03069(9) 0.08091(7) 0.0211(2) Uani 1 1 d . . . . .
C2 C 0.35486(11) -0.10513(10) 0.01801(8) 0.0249(3) Uani 1 1 d . . . . .
H2 H 0.289441 -0.084241 -0.009532 0.030 Uiso 1 1 calc R U . . .
C3 C 0.37010(12) -0.20952(10) -0.00466(8) 0.0277(3) Uani 1 1 d . . . . .
H3A H 0.314779 -0.259821 -0.047205 0.033 Uiso 1 1 calc R U . . .
C4 C 0.46573(13) -0.24033(10) 0.03462(9) 0.0290(3) Uani 1 1 d . . . . .
H4 H 0.476470 -0.311716 0.018678 0.035 Uiso 1 1 calc R U . . .
C5 C 0.54611(13) -0.16702(10) 0.09737(9) 0.0319(3) Uani 1 1 d . . . . .
H5 H 0.611916 -0.188301 0.124176 0.038 Uiso 1 1 calc R U . . .
C6 C 0.53039(12) -0.06252(10) 0.12100(9) 0.0278(3) Uani 1 1 d . . . . .
H6 H 0.584793 -0.012660 0.164553 0.033 Uiso 1 1 calc R U . . .
C7 C 0.42009(10) 0.08100(9) 0.10328(7) 0.0200(2) Uani 1 1 d . . . . .
C8 C 0.49275(10) 0.25099(9) 0.17056(7) 0.0195(2) Uani 1 1 d . . . . .
C9 C 0.58749(10) 0.32427(9) 0.22186(7) 0.0205(2) Uani 1 1 d . . . . .
H9 H 0.658004 0.301755 0.241359 0.025 Uiso 1 1 calc R U . . .
C10 C 0.57708(10) 0.42755(9) 0.24321(7) 0.0187(2) Uani 1 1 d . . . . .
C11 C 0.47294(10) 0.46519(9) 0.21555(7) 0.0185(2) Uani 1 1 d . . . . .
C12 C 0.38217(10) 0.39199(9) 0.16497(7) 0.0184(2) Uani 1 1 d . . . . .
C13 C 0.38760(10) 0.28383(9) 0.13918(7) 0.0192(2) Uani 1 1 d . . . . .
C14 C 0.29806(10) 0.20181(9) 0.08672(7) 0.0201(2) Uani 1 1 d . . . . .
C15 C 0.17994(11) 0.21488(10) 0.04724(8) 0.0233(2) Uani 1 1 d . . . . .
C16 C 0.08315(12) 0.15387(13) 0.05324(11) 0.0385(3) Uani 1 1 d . . . . .
H16 H 0.093659 0.109187 0.084468 0.046 Uiso 1 1 calc R U . . .
C17 C -0.02821(13) 0.15816(14) 0.01387(12) 0.0468(4) Uani 1 1 d . . . . .
H17 H -0.093568 0.116438 0.018368 0.056 Uiso 1 1 calc R U . . .
C18 C -0.04483(13) 0.22240(12) -0.03171(10) 0.0384(3) Uani 1 1 d . . . . .
H18 H -0.121677 0.226784 -0.057004 0.046 Uiso 1 1 calc R U . . .
C19 C 0.05071(13) 0.28048(10) -0.04054(8) 0.0310(3) Uani 1 1 d . . . . .
H19 H 0.039666 0.323279 -0.073330 0.037 Uiso 1 1 calc R U . . .
C20 C 0.16301(12) 0.27654(10) -0.00159(8) 0.0256(3) Uani 1 1 d . . . . .
H20 H 0.228412 0.316103 -0.008367 0.031 Uiso 1 1 calc R U . . .
C21 C 0.47577(10) 0.57959(9) 0.24100(7) 0.0196(2) Uani 1 1 d . . . . .
C22 C 0.36692(11) 0.63168(10) 0.24325(7) 0.0235(3) Uani 1 1 d . . . . .
C23 C 0.27459(12) 0.60330(11) 0.27694(9) 0.0322(3) Uani 1 1 d . . . . .
H23 H 0.277564 0.546894 0.296812 0.039 Uiso 1 1 calc R U . . .
C24 C 0.17773(14) 0.65818(14) 0.28134(11) 0.0453(4) Uani 1 1 d . . . . .
H24 H 0.114861 0.639579 0.304933 0.054 Uiso 1 1 calc R U . . .
C25 C 0.17240(15) 0.73960(14) 0.25161(11) 0.0475(4) Uani 1 1 d . . . . .
H25 H 0.105448 0.775944 0.254102 0.057 Uiso 1 1 calc R U . . .
C26 C 0.26400(15) 0.76817(13) 0.21836(10) 0.0425(4) Uani 1 1 d . . . . .
H26 H 0.260155 0.824265 0.198160 0.051 Uiso 1 1 calc R U . . .
C27 C 0.36170(13) 0.71505(11) 0.21439(8) 0.0311(3) Uani 1 1 d . . . . .
H27 H 0.425137 0.735299 0.192052 0.037 Uiso 1 1 calc R U . . .
C28 C 0.68224(10) 0.59243(9) 0.26228(7) 0.0185(2) Uani 1 1 d . . . . .
C29 C 0.71134(10) 0.54938(9) 0.17462(7) 0.0205(2) Uani 1 1 d . . . . .
C30 C 0.64082(11) 0.55686(10) 0.10573(8) 0.0250(3) Uani 1 1 d . . . . .
H30 H 0.572102 0.590524 0.111616 0.030 Uiso 1 1 calc R U . . .
C31 C 0.67076(13) 0.51502(11) 0.02799(8) 0.0309(3) Uani 1 1 d . . . . .
H31 H 0.621408 0.519216 -0.019061 0.037 Uiso 1 1 calc R U . . .
C32 C 0.77149(14) 0.46751(11) 0.01868(8) 0.0338(3) Uani 1 1 d . . . . .
H32 H 0.791798 0.439593 -0.034432 0.041 Uiso 1 1 calc R U . . .
C33 C 0.84295(14) 0.46087(11) 0.08767(9) 0.0351(3) Uani 1 1 d . . . . .
H33 H 0.912642 0.428695 0.081784 0.042 Uiso 1 1 calc R U . . .
C34 C 0.81273(12) 0.50108(10) 0.16496(8) 0.0287(3) Uani 1 1 d . . . . .
H34 H 0.861526 0.495686 0.211768 0.034 Uiso 1 1 calc R U . . .
C35 C 0.72618(10) 0.50688(9) 0.36916(7) 0.0199(2) Uani 1 1 d . . . . .
C36 C 0.68150(11) 0.43270(9) 0.40667(7) 0.0211(2) Uani 1 1 d . . . . .
C37 C 0.76249(11) 0.38431(10) 0.44439(8) 0.0247(3) Uani 1 1 d . . . . .
H37 H 0.843420 0.395468 0.442342 0.030 Uiso 1 1 calc R U . . .
C38 C 0.72518(12) 0.32005(11) 0.48481(9) 0.0302(3) Uani 1 1 d . . . . .
H38 H 0.780316 0.286460 0.509753 0.036 Uiso 1 1 calc R U . . .
C39 C 0.60728(12) 0.30487(11) 0.48878(9) 0.0323(3) Uani 1 1 d . . . . .
H39 H 0.581665 0.260743 0.516385 0.039 Uiso 1 1 calc R U . . .
C40 C 0.52673(12) 0.35395(11) 0.45255(9) 0.0302(3) Uani 1 1 d . . . . .
H40 H 0.446180 0.344072 0.456026 0.036 Uiso 1 1 calc R U . . .
C41 C 0.56328(11) 0.41735(10) 0.41130(8) 0.0250(3) Uani 1 1 d . . . . .
H41 H 0.507703 0.450384 0.386137 0.030 Uiso 1 1 calc R U . . .
C42 C 0.98820(10) 0.80432(9) 0.41177(7) 0.0186(2) Uani 1 1 d . . . . .
C43 C 0.95292(10) 0.71605(9) 0.42935(7) 0.0206(2) Uani 1 1 d . . . . .
H43 H 0.999359 0.700180 0.472225 0.025 Uiso 1 1 calc R U . . .
C44 C 0.85184(10) 0.65190(9) 0.38538(7) 0.0196(2) Uani 1 1 d . . . . .
C45 C 0.78403(10) 0.67170(9) 0.31837(7) 0.0179(2) Uani 1 1 d . . . . .
C46 C 0.81677(10) 0.76084(9) 0.30418(7) 0.0184(2) Uani 1 1 d . . . . .
C47 C 0.91737(10) 0.83164(9) 0.34955(7) 0.0177(2) Uani 1 1 d . . . . .
C48 C 0.95523(10) 0.92930(9) 0.34308(7) 0.0185(2) Uani 1 1 d . . . . .
C49 C 0.89396(10) 0.98036(9) 0.28823(7) 0.0197(2) Uani 1 1 d . . . . .
C50 C 0.87637(11) 0.93793(10) 0.20257(8) 0.0240(2) Uani 1 1 d . . . . .
H50 H 0.892912 0.869177 0.176515 0.029 Uiso 1 1 calc R U . . .
C51 C 0.83457(12) 0.99596(10) 0.15486(8) 0.0276(3) Uani 1 1 d . . . . .
H51 H 0.824540 0.967430 0.096374 0.033 Uiso 1 1 calc R U . . .
C52 C 0.80763(13) 1.09514(11) 0.19259(9) 0.0318(3) Uani 1 1 d . . . . .
H52 H 0.778299 1.134412 0.159981 0.038 Uiso 1 1 calc R U . . .
C53 C 0.82340(14) 1.13718(11) 0.27786(9) 0.0339(3) Uani 1 1 d . . . . .
H53 H 0.803713 1.204888 0.303638 0.041 Uiso 1 1 calc R U . . .
C54 C 0.86784(12) 1.08079(10) 0.32575(8) 0.0271(3) Uani 1 1 d . . . . .
H54 H 0.880512 1.110654 0.384265 0.033 Uiso 1 1 calc R U . . .
C55 C 1.11801(10) 0.95009(9) 0.44408(7) 0.0188(2) Uani 1 1 d . . . . .
C56 C 1.22897(10) 1.01575(9) 0.49167(7) 0.0207(2) Uani 1 1 d . . . . .
C57 C 1.25242(11) 1.11627(10) 0.49083(8) 0.0232(2) Uani 1 1 d . . . . .
H57 H 1.198414 1.142175 0.458208 0.028 Uiso 1 1 calc R U . . .
C58 C 1.35485(12) 1.17818(10) 0.53780(8) 0.0268(3) Uani 1 1 d . . . . .
H58 H 1.370055 1.246821 0.537718 0.032 Uiso 1 1 calc R U . . .
C59 C 1.43488(12) 1.14102(11) 0.58465(8) 0.0302(3) Uani 1 1 d . . . . .
H59 H 1.505051 1.183653 0.616330 0.036 Uiso 1 1 calc R U . . .
C60 C 1.41212(13) 1.04128(12) 0.58511(10) 0.0361(3) Uani 1 1 d . . . . .
H60 H 1.467064 1.015448 0.617189 0.043 Uiso 1 1 calc R U . . .
C61 C 1.30979(12) 0.97871(11) 0.53915(9) 0.0309(3) Uani 1 1 d . . . . .
H61 H 1.294770 0.910431 0.540053 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C12 1.3466(13) . ?
F2 C46 1.3479(13) . ?
N1 C14 1.3214(16) . ?
N1 C7 1.3672(16) . ?
N2 C7 1.3161(15) . ?
N2 C8 1.3597(15) . ?
N3 C21 1.2882(15) . ?
N3 C28 1.4674(15) . ?
N4 C35 1.3785(15) . ?
N4 C10 1.4134(14) . ?
N4 C28 1.4848(14) . ?
N5 C35 1.2906(15) . ?
N5 C44 1.3925(15) . ?
N6 C55 1.3151(15) . ?
N6 C42 1.3651(15) . ?
N7 C48 1.3238(15) . ?
N7 C55 1.3671(15) . ?
C1 C6 1.3954(18) . ?
C1 C2 1.3946(17) . ?
C1 C7 1.4832(16) . ?
C2 C3 1.3883(18) . ?
C3 C4 1.3824(19) . ?
C4 C5 1.3889(19) . ?
C5 C6 1.3906(18) . ?
C8 C9 1.4117(16) . ?
C8 C13 1.4257(16) . ?
C9 C10 1.3627(17) . ?
C10 C11 1.4275(16) . ?
C11 C12 1.3784(16) . ?
C11 C21 1.4836(16) . ?
C12 C13 1.4132(16) . ?
C13 C14 1.4394(16) . ?
C14 C15 1.4907(16) . ?
C15 C20 1.3917(18) . ?
C15 C16 1.3960(19) . ?
C16 C17 1.386(2) . ?
C17 C18 1.377(2) . ?
C18 C19 1.382(2) . ?
C19 C20 1.3915(18) . ?
C21 C22 1.4922(16) . ?
C22 C23 1.390(2) . ?
C22 C27 1.3988(19) . ?
C23 C24 1.392(2) . ?
C24 C25 1.383(3) . ?
C25 C26 1.379(3) . ?
C26 C27 1.387(2) . ?
C28 C45 1.5248(15) . ?
C28 C29 1.5438(16) . ?
C29 C30 1.3886(17) . ?
C29 C34 1.3936(18) . ?
C30 C31 1.3929(19) . ?
C31 C32 1.381(2) . ?
C32 C33 1.390(2) . ?
C33 C34 1.3853(19) . ?
C35 C36 1.4883(16) . ?
C36 C41 1.3934(18) . ?
C36 C37 1.3963(17) . ?
C37 C38 1.3863(18) . ?
C38 C39 1.387(2) . ?
C39 C40 1.3859(19) . ?
C40 C41 1.3852(18) . ?
C42 C43 1.3989(16) . ?
C42 C47 1.4296(16) . ?
C43 C44 1.3762(16) . ?
C44 C45 1.4242(16) . ?
C45 C46 1.3707(16) . ?
C46 C47 1.4163(16) . ?
C47 C48 1.4317(16) . ?
C48 C49 1.4919(16) . ?
C49 C50 1.3902(17) . ?
C49 C54 1.3938(17) . ?
C50 C51 1.3922(18) . ?
C51 C52 1.383(2) . ?
C52 C53 1.385(2) . ?
C53 C54 1.3862(18) . ?
C55 C56 1.4829(16) . ?
C56 C61 1.3926(18) . ?
C56 C57 1.3973(17) . ?
C57 C58 1.3884(17) . ?
C58 C59 1.381(2) . ?
C59 C60 1.383(2) . ?
C60 C61 1.3864(18) . ?

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
C14 N1 C7 118.84(10) . . ?
C7 N2 C8 116.65(10) . . ?
C21 N3 C28 117.42(10) . . ?
C35 N4 C10 123.59(10) . . ?
C35 N4 C28 123.75(9) . . ?
C10 N4 C28 111.87(9) . . ?
C35 N5 C44 118.39(10) . . ?
C55 N6 C42 116.86(10) . . ?
C48 N7 C55 118.87(10) . . ?
C6 C1 C2 119.14(11) . . ?
C6 C1 C7 120.57(11) . . ?
C2 C1 C7 120.27(11) . . ?
C3 C2 C1 120.48(12) . . ?
C4 C3 C2 120.05(12) . . ?
C3 C4 C5 120.07(12) . . ?
C4 C5 C6 120.08(13) . . ?
C5 C6 C1 120.17(12) . . ?
N2 C7 N1 125.94(11) . . ?
N2 C7 C1 117.87(11) . . ?
N1 C7 C1 116.19(10) . . ?
N2 C8 C9 116.80(10) . . ?
N2 C8 C13 122.42(11) . . ?
C9 C8 C13 120.77(11) . . ?
C10 C9 C8 119.52(11) . . ?
C9 C10 N4 122.41(10) . . ?
C9 C10 C11 122.31(11) . . ?
N4 C10 C11 115.27(10) . . ?
C12 C11 C10 116.96(10) . . ?
C12 C11 C21 126.57(10) . . ?
C10 C11 C21 116.40(10) . . ?
F1 C12 C11 118.02(10) . . ?
F1 C12 C13 118.19(10) . . ?
C11 C12 C13 123.78(11) . . ?
C12 C13 C8 116.61(10) . . ?
C12 C13 C14 127.85(11) . . ?
C8 C13 C14 115.52(11) . . ?
N1 C14 C13 120.62(11) . . ?
N1 C14 C15 113.09(10) . . ?
C13 C14 C15 126.28(11) . . ?
C20 C15 C16 118.77(12) . . ?
C20 C15 C14 123.30(11) . . ?
C16 C15 C14 117.62(12) . . ?
C17 C16 C15 120.34(14) . . ?
C18 C17 C16 120.52(15) . . ?
C17 C18 C19 119.74(13) . . ?
C18 C19 C20 120.27(13) . . ?
C19 C20 C15 120.29(13) . . ?
N3 C21 C11 121.85(10) . . ?
N3 C21 C22 115.67(10) . . ?
C11 C21 C22 122.48(10) . . ?
C23 C22 C27 119.74(12) . . ?
C23 C22 C21 121.94(12) . . ?
C27 C22 C21 118.22(12) . . ?
C22 C23 C24 119.49(15) . . ?
C25 C24 C23 120.46(16) . . ?
C26 C25 C24 120.20(14) . . ?
C25 C26 C27 120.04(16) . . ?
C26 C27 C22 120.05(15) . . ?
N3 C28 N4 108.98(9) . . ?
N3 C28 C45 110.11(9) . . ?
N4 C28 C45 108.99(9) . . ?
N3 C28 C29 111.66(9) . . ?
N4 C28 C29 108.26(9) . . ?
C45 C28 C29 108.78(9) . . ?
C30 C29 C34 119.16(12) . . ?
C30 C29 C28 122.72(11) . . ?
C34 C29 C28 118.12(11) . . ?
C29 C30 C31 120.05(13) . . ?
C32 C31 C30 120.63(13) . . ?
C31 C32 C33 119.45(13) . . ?
C34 C33 C32 120.15(14) . . ?
C33 C34 C29 120.55(13) . . ?
N5 C35 N4 124.07(11) . . ?
N5 C35 C36 116.16(10) . . ?
N4 C35 C36 119.73(10) . . ?
C41 C36 C37 119.47(11) . . ?
C41 C36 C35 121.86(11) . . ?
C37 C36 C35 118.44(11) . . ?
C38 C37 C36 120.21(12) . . ?
C39 C38 C37 119.91(12) . . ?
C38 C39 C40 120.14(12) . . ?
C41 C40 C39 120.22(12) . . ?
C40 C41 C36 120.04(12) . . ?
N6 C42 C43 117.55(10) . . ?
N6 C42 C47 122.00(10) . . ?
C43 C42 C47 120.42(10) . . ?
C44 C43 C42 120.88(11) . . ?
C43 C44 N5 117.24(10) . . ?
C43 C44 C45 120.36(11) . . ?
N5 C44 C45 122.27(10) . . ?
C46 C45 C44 117.99(10) . . ?
C46 C45 C28 121.83(10) . . ?
C44 C45 C28 120.11(10) . . ?
F2 C46 C45 118.06(10) . . ?
F2 C46 C47 118.08(10) . . ?
C45 C46 C47 123.85(10) . . ?
C46 C47 C42 116.20(10) . . ?
C46 C47 C48 128.21(10) . . ?
C42 C47 C48 115.55(10) . . ?
N7 C48 C47 120.83(10) . . ?
N7 C48 C49 112.17(10) . . ?
C47 C48 C49 126.99(10) . . ?
C50 C49 C54 119.41(11) . . ?
C50 C49 C48 122.86(11) . . ?
C54 C49 C48 117.18(11) . . ?
C51 C50 C49 120.16(12) . . ?
C52 C51 C50 120.03(12) . . ?
C53 C52 C51 120.01(12) . . ?
C52 C53 C54 120.21(12) . . ?
C53 C54 C49 120.14(12) . . ?
N6 C55 N7 125.68(11) . . ?
N6 C55 C56 118.37(10) . . ?
N7 C55 C56 115.94(10) . . ?
C61 C56 C57 119.27(11) . . ?
C61 C56 C55 120.32(11) . . ?
C57 C56 C55 120.40(11) . . ?
C58 C57 C56 119.82(12) . . ?
C59 C58 C57 120.70(12) . . ?
C58 C59 C60 119.52(12) . . ?
C59 C60 C61 120.55(13) . . ?
C60 C61 C56 120.13(13) . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.044



####################################################################### 
# 
# 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_ic21689
_database_code_depnum_ccdc_archive 'CCDC 2248150'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung. Liu'
;Instrument Center, National Taiwan University
Taiwan
;
_audit_update_record             
;
2023-03-13 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C47 H28 F3 N5'
_chemical_formula_weight         719.74

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'
N N 0.0311 0.0180 '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'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   16.0104(4)
_cell_length_b                   11.8607(3)
_cell_length_c                   18.9342(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.6407(9)
_cell_angle_gamma                90
_cell_volume                     3508.35(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9187
_cell_measurement_theta_min      4.09
_cell_measurement_theta_max      78.20

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.753
_shelx_estimated_absorpt_T_min   0.834
_shelx_estimated_absorpt_T_max   0.895
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8886
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            69512
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.086
_diffrn_reflns_theta_max         78.569
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             7323
_reflns_number_gt                6916
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0668P)²+1.3569P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7323
_refine_ls_number_parameters     496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1154
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.54357(5) 0.29779(6) 0.19497(4) 0.02497(17) Uani 1 1 d . . . . .
F2 F 0.01257(5) 0.48803(7) 0.39137(5) 0.0356(2) Uani 1 1 d . . . . .
F3 F 0.16416(4) 0.29395(6) 0.24463(4) 0.02379(16) Uani 1 1 d . . . . .
N1 N 0.64983(6) 0.59705(8) 0.13076(5) 0.0213(2) Uani 1 1 d . . . . .
N2 N 0.58479(6) 0.69819(8) 0.21397(5) 0.0187(2) Uani 1 1 d . . . . .
N3 N 0.37923(6) 0.51049(8) 0.32360(5) 0.0169(2) Uani 1 1 d . . . . .
N4 N 0.35503(6) 0.31286(8) 0.30784(5) 0.0174(2) Uani 1 1 d . . . . .
N5 N 0.30117(6) 0.58730(8) 0.40442(5) 0.0190(2) Uani 1 1 d . . . . .
C1 C 0.67944(8) 0.89193(11) 0.19634(7) 0.0261(3) Uani 1 1 d . . . . .
H1 H 0.647842 0.891570 0.233361 0.031 Uiso 1 1 calc R U . . .
C2 C 0.72442(9) 0.98781(12) 0.18484(8) 0.0312(3) Uani 1 1 d . . . . .
H2 H 0.723771 1.052694 0.214136 0.037 Uiso 1 1 calc R U . . .
C3 C 0.77036(9) 0.98896(11) 0.13056(8) 0.0299(3) Uani 1 1 d . . . . .
H3 H 0.802413 1.053895 0.123699 0.036 Uiso 1 1 calc R U . . .
C4 C 0.76957(8) 0.89603(12) 0.08653(7) 0.0288(3) Uani 1 1 d . . . . .
H4 H 0.799551 0.897944 0.048436 0.035 Uiso 1 1 calc R U . . .
C5 C 0.72484(8) 0.79948(11) 0.09794(7) 0.0250(3) Uani 1 1 d . . . . .
H5 H 0.724517 0.735617 0.067601 0.030 Uiso 1 1 calc R U . . .
C6 C 0.68044(7) 0.79593(10) 0.15372(6) 0.0203(2) Uani 1 1 d . . . . .
C7 C 0.63548(7) 0.69174(10) 0.16781(6) 0.0190(2) Uani 1 1 d . . . . .
C8 C 0.54741(7) 0.60053(9) 0.22913(6) 0.0174(2) Uani 1 1 d . . . . .
C9 C 0.48925(7) 0.60707(10) 0.27503(6) 0.0178(2) Uani 1 1 d . . . . .
H9 H 0.477343 0.677369 0.294775 0.021 Uiso 1 1 calc R U . . .
C10 C 0.45020(7) 0.51065(9) 0.29074(6) 0.0168(2) Uani 1 1 d . . . . .
C11 C 0.31553(7) 0.42423(9) 0.28958(6) 0.0167(2) Uani 1 1 d . . . . .
C12 C 0.43149(7) 0.30370(9) 0.29628(6) 0.0173(2) Uani 1 1 d . . . . .
C13 C 0.47296(7) 0.40174(9) 0.26875(6) 0.0173(2) Uani 1 1 d . . . . .
C14 C 0.52612(7) 0.39824(9) 0.22085(6) 0.0187(2) Uani 1 1 d . . . . .
C15 C 0.56224(7) 0.49620(10) 0.19705(6) 0.0181(2) Uani 1 1 d . . . . .
C16 C 0.61270(7) 0.50216(10) 0.14366(6) 0.0202(2) Uani 1 1 d . . . . .
C17 C 0.62672(8) 0.40351(10) 0.09917(7) 0.0236(3) Uani 1 1 d . . . . .
C18 C 0.70947(9) 0.36255(11) 0.10597(8) 0.0293(3) Uani 1 1 d . . . . .
H18 H 0.755793 0.397070 0.138819 0.035 Uiso 1 1 calc R U . . .
C19 C 0.72416(11) 0.27131(12) 0.06473(9) 0.0377(3) Uani 1 1 d . . . . .
H19 H 0.780593 0.242706 0.069871 0.045 Uiso 1 1 calc R U . . .
C20 C 0.65782(13) 0.22195(13) 0.01653(9) 0.0448(4) Uani 1 1 d . . . . .
H20 H 0.668420 0.159279 -0.011499 0.054 Uiso 1 1 calc R U . . .
C21 C 0.57533(13) 0.26330(15) 0.00862(9) 0.0472(4) Uani 1 1 d . . . . .
H21 H 0.529606 0.229652 -0.025341 0.057 Uiso 1 1 calc R U . . .
C22 C 0.55939(10) 0.35408(13) 0.05037(8) 0.0357(3) Uani 1 1 d . . . . .
H22 H 0.502792 0.381988 0.045474 0.043 Uiso 1 1 calc R U . . .
C23 C 0.47855(7) 0.19653(9) 0.31656(6) 0.0188(2) Uani 1 1 d . . . . .
C24 C 0.56775(8) 0.19259(10) 0.33539(7) 0.0240(3) Uani 1 1 d . . . . .
H24 H 0.600100 0.258597 0.331631 0.029 Uiso 1 1 calc R U . . .
C25 C 0.60957(8) 0.09236(11) 0.35968(8) 0.0281(3) Uani 1 1 d . . . . .
H25 H 0.670340 0.090207 0.372293 0.034 Uiso 1 1 calc R U . . .
C26 C 0.56294(9) -0.00422(11) 0.36552(7) 0.0277(3) Uani 1 1 d . . . . .
H26 H 0.591554 -0.072532 0.382183 0.033 Uiso 1 1 calc R U . . .
C27 C 0.47414(9) -0.00067(10) 0.34690(7) 0.0256(3) Uani 1 1 d . . . . .
H27 H 0.442019 -0.066666 0.351240 0.031 Uiso 1 1 calc R U . . .
C28 C 0.43209(8) 0.09842(10) 0.32204(6) 0.0218(2) Uani 1 1 d . . . . .
H28 H 0.371348 0.099700 0.308632 0.026 Uiso 1 1 calc R U . . .
C29 C 0.29494(7) 0.44215(10) 0.20665(6) 0.0182(2) Uani 1 1 d . . . . .
C30 C 0.28945(8) 0.35203(11) 0.15871(6) 0.0230(2) Uani 1 1 d . . . . .
H30 H 0.293631 0.276911 0.176551 0.028 Uiso 1 1 calc R U . . .
C31 C 0.27785(9) 0.37169(12) 0.08477(7) 0.0296(3) Uani 1 1 d . . . . .
H31 H 0.274289 0.309851 0.052357 0.036 Uiso 1 1 calc R U . . .
C32 C 0.27149(9) 0.48054(13) 0.05817(7) 0.0323(3) Uani 1 1 d . . . . .
H32 H 0.264434 0.493711 0.007714 0.039 Uiso 1 1 calc R U . . .
C33 C 0.27549(8) 0.57064(12) 0.10572(7) 0.0287(3) Uani 1 1 d . . . . .
H33 H 0.270934 0.645652 0.087688 0.034 Uiso 1 1 calc R U . . .
C34 C 0.28609(7) 0.55145(10) 0.17935(7) 0.0221(2) Uani 1 1 d . . . . .
H34 H 0.287325 0.613355 0.211401 0.027 Uiso 1 1 calc R U . . .
C35 C 0.43703(8) 0.74339(10) 0.45026(6) 0.0216(2) Uani 1 1 d . . . . .
H35 H 0.383001 0.779709 0.436714 0.026 Uiso 1 1 calc R U . . .
C36 C 0.50460(9) 0.79777(11) 0.49590(7) 0.0260(3) Uani 1 1 d . . . . .
H36 H 0.496929 0.871403 0.513183 0.031 Uiso 1 1 calc R U . . .
C37 C 0.58336(8) 0.74461(12) 0.51629(7) 0.0266(3) Uani 1 1 d . . . . .
H37 H 0.629496 0.781715 0.547810 0.032 Uiso 1 1 calc R U . . .
C38 C 0.59493(8) 0.63729(11) 0.49074(6) 0.0231(2) Uani 1 1 d . . . . .
H38 H 0.648953 0.601141 0.504949 0.028 Uiso 1 1 calc R U . . .
C39 C 0.52771(7) 0.58242(10) 0.44440(6) 0.0198(2) Uani 1 1 d . . . . .
H39 H 0.535834 0.509269 0.426591 0.024 Uiso 1 1 calc R U . . .
C40 C 0.44797(7) 0.63585(10) 0.42420(6) 0.0176(2) Uani 1 1 d . . . . .
C41 C 0.37133(7) 0.57643(9) 0.38165(6) 0.0169(2) Uani 1 1 d . . . . .
C42 C 0.23080(7) 0.52203(10) 0.37128(6) 0.0186(2) Uani 1 1 d . . . . .
C43 C 0.15474(8) 0.53980(11) 0.39499(7) 0.0231(2) Uani 1 1 d . . . . .
H43 H 0.151210 0.597401 0.429085 0.028 Uiso 1 1 calc R U . . .
C44 C 0.08547(8) 0.47219(11) 0.36789(7) 0.0247(3) Uani 1 1 d . . . . .
C45 C 0.08705(7) 0.38724(10) 0.31860(7) 0.0229(2) Uani 1 1 d . . . . .
H45 H 0.038773 0.340407 0.301307 0.027 Uiso 1 1 calc R U . . .
C46 C 0.16275(7) 0.37383(10) 0.29565(6) 0.0195(2) Uani 1 1 d . . . . .
C47 C 0.23568(7) 0.43853(9) 0.31982(6) 0.0174(2) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.3407(13) . ?
F2 C44 1.3499(13) . ?
F3 C46 1.3567(13) . ?
N1 C16 1.3203(15) . ?
N1 C7 1.3699(15) . ?
N2 C7 1.3188(14) . ?
N2 C8 1.3629(15) . ?
N3 C41 1.3772(14) . ?
N3 C10 1.4097(14) . ?
N3 C11 1.4880(14) . ?
N4 C12 1.2944(14) . ?
N4 C11 1.4726(14) . ?
N5 C41 1.2946(14) . ?
N5 C42 1.3975(15) . ?
C1 C2 1.3886(18) . ?
C1 C6 1.3977(17) . ?
C2 C3 1.389(2) . ?
C3 C4 1.380(2) . ?
C4 C5 1.3923(18) . ?
C5 C6 1.3968(16) . ?
C6 C7 1.4834(16) . ?
C8 C9 1.4080(15) . ?
C8 C15 1.4213(16) . ?
C9 C10 1.3669(16) . ?
C10 C13 1.4288(15) . ?
C11 C47 1.5203(15) . ?
C11 C29 1.5469(15) . ?
C12 C23 1.4846(15) . ?
C12 C13 1.4886(15) . ?
C13 C14 1.3736(15) . ?
C14 C15 1.4147(16) . ?
C15 C16 1.4273(15) . ?
C16 C17 1.4872(16) . ?
C17 C22 1.387(2) . ?
C17 C18 1.3905(18) . ?
C18 C19 1.3843(19) . ?
C19 C20 1.371(3) . ?
C20 C21 1.386(3) . ?
C21 C22 1.392(2) . ?
C23 C24 1.3949(16) . ?
C23 C28 1.3971(16) . ?
C24 C25 1.3923(17) . ?
C25 C26 1.3849(19) . ?
C26 C27 1.3885(19) . ?
C27 C28 1.3847(17) . ?
C29 C34 1.3914(17) . ?
C29 C30 1.3926(17) . ?
C30 C31 1.3910(17) . ?
C31 C32 1.381(2) . ?
C32 C33 1.390(2) . ?
C33 C34 1.3858(18) . ?
C35 C36 1.3869(17) . ?
C35 C40 1.3924(16) . ?
C36 C37 1.3870(19) . ?
C37 C38 1.3884(19) . ?
C38 C39 1.3924(17) . ?
C39 C40 1.4014(16) . ?
C40 C41 1.4896(15) . ?
C42 C43 1.4029(16) . ?
C42 C47 1.4035(16) . ?
C43 C44 1.3738(18) . ?
C44 C45 1.3773(18) . ?
C45 C46 1.3833(16) . ?
C46 C47 1.3885(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N1 C7 118.12(10) . . ?
C7 N2 C8 116.91(10) . . ?
C41 N3 C10 125.11(9) . . ?
C41 N3 C11 124.19(9) . . ?
C10 N3 C11 110.62(9) . . ?
C12 N4 C11 114.15(9) . . ?
C41 N5 C42 117.93(10) . . ?
C2 C1 C6 120.32(12) . . ?
C1 C2 C3 120.07(13) . . ?
C4 C3 C2 120.19(12) . . ?
C3 C4 C5 120.00(12) . . ?
C4 C5 C6 120.42(12) . . ?
C5 C6 C1 118.95(11) . . ?
C5 C6 C7 120.56(11) . . ?
C1 C6 C7 120.49(10) . . ?
N2 C7 N1 125.70(10) . . ?
N2 C7 C6 117.65(10) . . ?
N1 C7 C6 116.65(10) . . ?
N2 C8 C9 117.61(10) . . ?
N2 C8 C15 121.86(10) . . ?
C9 C8 C15 120.45(10) . . ?
C10 C9 C8 118.95(10) . . ?
C9 C10 N3 123.26(10) . . ?
C9 C10 C13 122.34(10) . . ?
N3 C10 C13 114.14(9) . . ?
N4 C11 N3 107.26(9) . . ?
N4 C11 C47 111.41(9) . . ?
N3 C11 C47 108.27(9) . . ?
N4 C11 C29 110.28(9) . . ?
N3 C11 C29 108.58(8) . . ?
C47 C11 C29 110.91(9) . . ?
N4 C12 C23 118.25(10) . . ?
N4 C12 C13 120.29(10) . . ?
C23 C12 C13 121.29(10) . . ?
C14 C13 C10 117.01(10) . . ?
C14 C13 C12 126.58(10) . . ?
C10 C13 C12 116.26(9) . . ?
F1 C14 C13 118.49(10) . . ?
F1 C14 C15 118.75(10) . . ?
C13 C14 C15 122.76(10) . . ?
C14 C15 C8 117.43(10) . . ?
C14 C15 C16 126.91(10) . . ?
C8 C15 C16 115.66(10) . . ?
N1 C16 C15 121.39(10) . . ?
N1 C16 C17 115.85(10) . . ?
C15 C16 C17 122.76(10) . . ?
C22 C17 C18 120.00(12) . . ?
C22 C17 C16 121.22(12) . . ?
C18 C17 C16 118.77(12) . . ?
C19 C18 C17 119.79(14) . . ?
C20 C19 C18 120.46(15) . . ?
C19 C20 C21 120.13(14) . . ?
C20 C21 C22 120.07(16) . . ?
C17 C22 C21 119.54(15) . . ?
C24 C23 C28 119.01(11) . . ?
C24 C23 C12 121.87(10) . . ?
C28 C23 C12 118.95(10) . . ?
C25 C24 C23 120.30(11) . . ?
C26 C25 C24 120.26(12) . . ?
C25 C26 C27 119.64(11) . . ?
C28 C27 C26 120.44(11) . . ?
C27 C28 C23 120.34(11) . . ?
C34 C29 C30 119.09(11) . . ?
C34 C29 C11 119.14(10) . . ?
C30 C29 C11 121.68(10) . . ?
C31 C30 C29 120.19(12) . . ?
C32 C31 C30 120.44(12) . . ?
C31 C32 C33 119.55(12) . . ?
C34 C33 C32 120.23(12) . . ?
C33 C34 C29 120.46(12) . . ?
C36 C35 C40 120.35(11) . . ?
C35 C36 C37 119.98(12) . . ?
C36 C37 C38 120.15(11) . . ?
C37 C38 C39 120.30(11) . . ?
C38 C39 C40 119.53(11) . . ?
C35 C40 C39 119.69(11) . . ?
C35 C40 C41 118.19(10) . . ?
C39 C40 C41 121.80(10) . . ?
N5 C41 N3 124.07(10) . . ?
N5 C41 C40 116.42(10) . . ?
N3 C41 C40 119.45(9) . . ?
N5 C42 C43 116.37(10) . . ?
N5 C42 C47 122.73(10) . . ?
C43 C42 C47 120.82(11) . . ?
C44 C43 C42 118.62(11) . . ?
F2 C44 C43 118.76(11) . . ?
F2 C44 C45 118.06(11) . . ?
C43 C44 C45 123.17(11) . . ?
C44 C45 C46 116.38(11) . . ?
F3 C46 C45 117.15(10) . . ?
F3 C46 C47 118.48(10) . . ?
C45 C46 C47 124.35(11) . . ?
C46 C47 C42 116.63(10) . . ?
C46 C47 C11 122.01(10) . . ?
C42 C47 C11 121.29(10) . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_ic21862_sq
_database_code_depnum_ccdc_archive 'CCDC 2250630'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung. Liu'
;Instrument Center, National Taiwan University
Taiwan
;
_audit_update_record             
;
2023-03-22 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
9'-(2,4-diphenylquinazolin-5-yl)-9'H-9,3':6',9''-tercarbazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H35 N5'
_chemical_formula_weight         777.89

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   13.4479(4)
_cell_length_b                   14.7090(4)
_cell_length_c                   23.9088(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.8572(13)
_cell_angle_gamma                90
_cell_volume                     4718.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9396
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      78.37

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.095
_exptl_crystal_F_000             1624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.502
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8516
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            94466
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.530
_diffrn_reflns_theta_max         78.868
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             9891
_reflns_number_gt                8872
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 Structure factors included contributions from the .fab file. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1060P)²+2.4445P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9891
_refine_ls_number_parameters     550
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1771
_refine_ls_wR_factor_gt          0.1716
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
N1 N 0.58835(11) 0.71805(10) 0.55425(6) 0.0317(3) Uani 1 1 d . . . . .
N2 N 0.70551(11) 0.68665(10) 0.63125(6) 0.0292(3) Uani 1 1 d . . . . .
N3 N 0.56546(10) 0.42203(9) 0.64781(6) 0.0264(3) Uani 1 1 d . . . . .
N4 N 0.93495(10) 0.25843(9) 0.68987(6) 0.0278(3) Uani 1 1 d . . . . .
N5 N 0.40005(10) 0.21914(9) 0.81437(6) 0.0284(3) Uani 1 1 d . . . . .
C1 C 0.54013(12) 0.63883(12) 0.56479(7) 0.0297(3) Uani 1 1 d . . . . .
C2 C 0.45173(13) 0.61875(13) 0.53157(8) 0.0341(4) Uani 1 1 d . . . . .
H2A H 0.425805 0.661276 0.504459 0.041 Uiso 1 1 calc R U . . .
C3 C 0.40391(13) 0.53826(13) 0.53857(8) 0.0347(4) Uani 1 1 d . . . . .
H3A H 0.343580 0.525638 0.516990 0.042 Uiso 1 1 calc R U . . .
C4 C 0.44312(13) 0.47370(12) 0.57748(8) 0.0327(4) Uani 1 1 d . . . . .
H4A H 0.410732 0.416688 0.580500 0.039 Uiso 1 1 calc R U . . .
C5 C 0.52753(12) 0.49190(11) 0.61116(7) 0.0283(3) Uani 1 1 d . . . . .
C6 C 0.57609(12) 0.57783(11) 0.60794(7) 0.0276(3) Uani 1 1 d . . . . .
C7 C 0.65767(12) 0.61186(11) 0.64390(7) 0.0276(3) Uani 1 1 d . . . . .
C8 C 0.68941(12) 0.57235(11) 0.69951(7) 0.0275(3) Uani 1 1 d . . . . .
C9 C 0.61926(13) 0.55578(11) 0.73847(7) 0.0300(3) Uani 1 1 d . . . . .
H9A H 0.550383 0.564495 0.728370 0.036 Uiso 1 1 calc R U . . .
C10 C 0.64972(14) 0.52663(12) 0.79189(8) 0.0337(4) Uani 1 1 d . . . . .
H10A H 0.601620 0.515642 0.818433 0.040 Uiso 1 1 calc R U . . .
C11 C 0.74984(15) 0.51337(13) 0.80692(8) 0.0360(4) Uani 1 1 d . . . . .
H11A H 0.770271 0.492958 0.843609 0.043 Uiso 1 1 calc R U . . .
C12 C 0.82071(13) 0.52997(12) 0.76821(8) 0.0328(4) Uani 1 1 d . . . . .
H12A H 0.889447 0.520603 0.778411 0.039 Uiso 1 1 calc R U . . .
C13 C 0.79066(13) 0.56017(11) 0.71479(7) 0.0289(3) Uani 1 1 d . . . . .
H13A H 0.838928 0.572600 0.688572 0.035 Uiso 1 1 calc R U . . .
C14 C 0.66972(13) 0.73565(12) 0.58590(7) 0.0296(3) Uani 1 1 d . . . . .
C15 C 0.72549(13) 0.81944(12) 0.57366(7) 0.0315(4) Uani 1 1 d . . . . .
C16 C 0.82426(14) 0.83130(13) 0.59432(8) 0.0357(4) Uani 1 1 d . . . . .
H16A H 0.855821 0.786159 0.617734 0.043 Uiso 1 1 calc R U . . .
C17 C 0.87654(15) 0.90878(14) 0.58079(8) 0.0392(4) Uani 1 1 d . . . . .
H17A H 0.944260 0.915861 0.594091 0.047 Uiso 1 1 calc R U . . .
C18 C 0.83003(16) 0.97531(14) 0.54806(8) 0.0418(4) Uani 1 1 d . . . . .
H18A H 0.865764 1.028522 0.539157 0.050 Uiso 1 1 calc R U . . .
C19 C 0.73195(17) 0.96537(15) 0.52806(9) 0.0456(5) Uani 1 1 d . . . . .
H19A H 0.700347 1.011947 0.505818 0.055 Uiso 1 1 calc R U . . .
C20 C 0.67928(15) 0.88738(13) 0.54038(8) 0.0393(4) Uani 1 1 d . . . . .
H20A H 0.612028 0.880312 0.526208 0.047 Uiso 1 1 calc R U . . .
C21 C 0.51230(12) 0.37908(11) 0.68828(7) 0.0266(3) Uani 1 1 d . . . . .
C22 C 0.41454(12) 0.39419(12) 0.70279(8) 0.0314(4) Uani 1 1 d . . . . .
H22A H 0.374141 0.439904 0.684711 0.038 Uiso 1 1 calc R U . . .
C23 C 0.37884(12) 0.34024(12) 0.74436(8) 0.0317(4) Uani 1 1 d . . . . .
H23A H 0.312155 0.347886 0.754331 0.038 Uiso 1 1 calc R U . . .
C24 C 0.43947(12) 0.27437(11) 0.77205(7) 0.0280(3) Uani 1 1 d . . . . .
C25 C 0.53760(12) 0.26164(11) 0.75912(7) 0.0271(3) Uani 1 1 d . . . . .
H25A H 0.578900 0.218259 0.778832 0.033 Uiso 1 1 calc R U . . .
C26 C 0.57387(11) 0.31400(11) 0.71660(7) 0.0259(3) Uani 1 1 d . . . . .
C27 C 0.66947(11) 0.31897(11) 0.69255(7) 0.0251(3) Uani 1 1 d . . . . .
C28 C 0.75974(12) 0.27426(11) 0.70468(7) 0.0268(3) Uani 1 1 d . . . . .
H28A H 0.766161 0.229586 0.733396 0.032 Uiso 1 1 calc R U . . .
C29 C 0.83984(11) 0.29656(11) 0.67385(7) 0.0266(3) Uani 1 1 d . . . . .
C30 C 0.82974(12) 0.35947(11) 0.62976(7) 0.0284(3) Uani 1 1 d . . . . .
H30A H 0.885459 0.372205 0.608634 0.034 Uiso 1 1 calc R U . . .
C31 C 0.74004(12) 0.40352(11) 0.61635(7) 0.0275(3) Uani 1 1 d . . . . .
H31A H 0.732703 0.444901 0.585844 0.033 Uiso 1 1 calc R U . . .
C32 C 0.66110(11) 0.38457(11) 0.64946(7) 0.0254(3) Uani 1 1 d . . . . .
C33 C 0.36838(12) 0.24972(12) 0.86517(7) 0.0290(3) Uani 1 1 d . . . . .
C34 C 0.36254(13) 0.33837(13) 0.88501(8) 0.0352(4) Uani 1 1 d . . . . .
H34A H 0.381691 0.388707 0.863276 0.042 Uiso 1 1 calc R U . . .
C35 C 0.32781(15) 0.35020(14) 0.93754(9) 0.0420(4) Uani 1 1 d . . . . .
H35A H 0.322859 0.410059 0.952023 0.050 Uiso 1 1 calc R U . . .
C36 C 0.29967(15) 0.27678(15) 0.97010(8) 0.0410(4) Uani 1 1 d . . . . .
H36A H 0.276286 0.287403 1.006147 0.049 Uiso 1 1 calc R U . . .
C37 C 0.30568(13) 0.18840(14) 0.95011(8) 0.0366(4) Uani 1 1 d . . . . .
H37A H 0.287102 0.138435 0.972325 0.044 Uiso 1 1 calc R U . . .
C38 C 0.33947(12) 0.17415(12) 0.89683(7) 0.0301(3) Uani 1 1 d . . . . .
C39 C 0.35303(12) 0.09437(12) 0.86284(7) 0.0299(3) Uani 1 1 d . . . . .
C40 C 0.33521(14) 0.00142(12) 0.87002(8) 0.0350(4) Uani 1 1 d . . . . .
H40A H 0.310437 -0.020455 0.903791 0.042 Uiso 1 1 calc R U . . .
C41 C 0.35427(14) -0.05816(13) 0.82713(9) 0.0390(4) Uani 1 1 d . . . . .
H41A H 0.343173 -0.121409 0.831810 0.047 Uiso 1 1 calc R U . . .
C42 C 0.38960(14) -0.02635(13) 0.77709(9) 0.0375(4) Uani 1 1 d . . . . .
H42A H 0.400877 -0.068377 0.748013 0.045 Uiso 1 1 calc R U . . .
C43 C 0.40858(13) 0.06524(12) 0.76891(8) 0.0331(4) Uani 1 1 d . . . . .
H43A H 0.432914 0.086574 0.734901 0.040 Uiso 1 1 calc R U . . .
C44 C 0.39062(12) 0.12478(11) 0.81242(7) 0.0283(3) Uani 1 1 d . . . . .
C45 C 0.98189(11) 0.26582(11) 0.74340(7) 0.0270(3) Uani 1 1 d . . . . .
C46 C 0.95179(12) 0.31319(12) 0.78982(7) 0.0302(3) Uani 1 1 d . . . . .
H46A H 0.890112 0.344865 0.788409 0.036 Uiso 1 1 calc R U . . .
C47 C 1.01471(14) 0.31253(13) 0.83800(8) 0.0357(4) Uani 1 1 d . . . . .
H47A H 0.996516 0.345346 0.869976 0.043 Uiso 1 1 calc R U . . .
C48 C 1.10484(14) 0.26436(14) 0.84055(8) 0.0389(4) Uani 1 1 d . . . . .
H48A H 1.146378 0.264509 0.874304 0.047 Uiso 1 1 calc R U . . .
C49 C 1.13407(13) 0.21672(13) 0.79472(8) 0.0364(4) Uani 1 1 d . . . . .
H49A H 1.194877 0.183635 0.796881 0.044 Uiso 1 1 calc R U . . .
C50 C 1.07300(12) 0.21782(11) 0.74509(8) 0.0299(3) Uani 1 1 d . . . . .
C51 C 1.08034(12) 0.17883(11) 0.69011(8) 0.0311(4) Uani 1 1 d . . . . .
C52 C 1.15116(14) 0.12386(13) 0.66638(10) 0.0402(4) Uani 1 1 d . . . . .
H52A H 1.209715 0.105373 0.687816 0.048 Uiso 1 1 calc R U . . .
C53 C 1.13445(15) 0.09697(14) 0.61126(10) 0.0454(5) Uani 1 1 d . . . . .
H53A H 1.182073 0.059574 0.594748 0.054 Uiso 1 1 calc R U . . .
C54 C 1.04899(15) 0.12373(14) 0.57948(9) 0.0439(5) Uani 1 1 d . . . . .
H54A H 1.039469 0.104101 0.541645 0.053 Uiso 1 1 calc R U . . .
C55 C 0.97722(13) 0.17845(13) 0.60169(8) 0.0362(4) Uani 1 1 d . . . . .
H55A H 0.918923 0.196559 0.579879 0.043 Uiso 1 1 calc R U . . .
C56 C 0.99432(12) 0.20551(11) 0.65710(8) 0.0295(3) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C14 1.314(2) . ?
N1 C1 1.365(2) . ?
N2 C7 1.320(2) . ?
N2 C14 1.363(2) . ?
N3 C21 1.393(2) . ?
N3 C32 1.397(2) . ?
N3 C5 1.423(2) . ?
N4 C45 1.393(2) . ?
N4 C56 1.393(2) . ?
N4 C29 1.425(2) . ?
N5 C33 1.389(2) . ?
N5 C44 1.394(2) . ?
N5 C24 1.427(2) . ?
C1 C2 1.416(2) . ?
C1 C6 1.427(2) . ?
C2 C3 1.363(3) . ?
C3 C4 1.407(3) . ?
C4 C5 1.373(2) . ?
C5 C6 1.427(2) . ?
C6 C7 1.438(2) . ?
C7 C8 1.487(2) . ?
C8 C9 1.391(2) . ?
C8 C13 1.397(2) . ?
C9 C10 1.383(3) . ?
C10 C11 1.384(3) . ?
C11 C12 1.394(3) . ?
C12 C13 1.387(2) . ?
C14 C15 1.482(2) . ?
C15 C20 1.397(3) . ?
C15 C16 1.397(3) . ?
C16 C17 1.389(3) . ?
C17 C18 1.377(3) . ?
C18 C19 1.380(3) . ?
C19 C20 1.390(3) . ?
C21 C22 1.400(2) . ?
C21 C26 1.409(2) . ?
C22 C23 1.383(3) . ?
C23 C24 1.403(2) . ?
C24 C25 1.388(2) . ?
C25 C26 1.390(2) . ?
C26 C27 1.445(2) . ?
C27 C28 1.394(2) . ?
C27 C32 1.410(2) . ?
C28 C29 1.385(2) . ?
C29 C30 1.402(2) . ?
C30 C31 1.388(2) . ?
C31 C32 1.394(2) . ?
C33 C34 1.392(2) . ?
C33 C38 1.414(2) . ?
C34 C35 1.380(3) . ?
C35 C36 1.398(3) . ?
C36 C37 1.389(3) . ?
C37 C38 1.397(3) . ?
C38 C39 1.446(2) . ?
C39 C40 1.401(2) . ?
C39 C44 1.411(2) . ?
C40 C41 1.386(3) . ?
C41 C42 1.397(3) . ?
C42 C43 1.387(3) . ?
C43 C44 1.393(2) . ?
C45 C46 1.393(2) . ?
C45 C50 1.412(2) . ?
C46 C47 1.383(3) . ?
C47 C48 1.402(3) . ?
C48 C49 1.380(3) . ?
C49 C50 1.397(3) . ?
C50 C51 1.444(3) . ?
C51 C52 1.398(2) . ?
C51 C56 1.412(2) . ?
C52 C53 1.380(3) . ?
C53 C54 1.391(3) . ?
C54 C55 1.389(3) . ?
C55 C56 1.387(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
C14 N1 C1 116.72(15) . . ?
C7 N2 C14 118.15(15) . . ?
C21 N3 C32 108.42(13) . . ?
C21 N3 C5 125.18(13) . . ?
C32 N3 C5 126.40(14) . . ?
C45 N4 C56 108.59(13) . . ?
C45 N4 C29 124.01(14) . . ?
C56 N4 C29 127.34(15) . . ?
C33 N5 C44 108.61(14) . . ?
C33 N5 C24 125.88(14) . . ?
C44 N5 C24 125.46(14) . . ?
N1 C1 C2 117.77(15) . . ?
N1 C1 C6 121.87(15) . . ?
C2 C1 C6 120.35(16) . . ?
C3 C2 C1 119.85(16) . . ?
C2 C3 C4 120.56(16) . . ?
C5 C4 C3 120.97(17) . . ?
C4 C5 N3 117.93(15) . . ?
C4 C5 C6 120.28(15) . . ?
N3 C5 C6 121.78(14) . . ?
C1 C6 C5 117.51(15) . . ?
C1 C6 C7 114.92(15) . . ?
C5 C6 C7 127.57(15) . . ?
N2 C7 C6 121.16(15) . . ?
N2 C7 C8 114.56(15) . . ?
C6 C7 C8 124.07(15) . . ?
C9 C8 C13 119.68(16) . . ?
C9 C8 C7 120.02(15) . . ?
C13 C8 C7 120.00(15) . . ?
C10 C9 C8 120.04(16) . . ?
C9 C10 C11 120.41(17) . . ?
C10 C11 C12 119.97(17) . . ?
C13 C12 C11 119.85(17) . . ?
C12 C13 C8 120.03(16) . . ?
N1 C14 N2 126.16(16) . . ?
N1 C14 C15 117.59(15) . . ?
N2 C14 C15 116.15(15) . . ?
C20 C15 C16 119.22(17) . . ?
C20 C15 C14 119.72(16) . . ?
C16 C15 C14 121.06(16) . . ?
C17 C16 C15 120.30(18) . . ?
C18 C17 C16 119.87(19) . . ?
C17 C18 C19 120.57(19) . . ?
C18 C19 C20 120.18(19) . . ?
C19 C20 C15 119.84(19) . . ?
N3 C21 C22 129.40(15) . . ?
N3 C21 C26 109.24(14) . . ?
C22 C21 C26 121.35(15) . . ?
C23 C22 C21 117.66(15) . . ?
C22 C23 C24 121.10(15) . . ?
C25 C24 C23 121.26(16) . . ?
C25 C24 N5 119.02(15) . . ?
C23 C24 N5 119.71(14) . . ?
C26 C25 C24 118.29(15) . . ?
C25 C26 C21 120.28(15) . . ?
C25 C26 C27 133.20(15) . . ?
C21 C26 C27 106.52(14) . . ?
C28 C27 C32 120.03(14) . . ?
C28 C27 C26 132.76(15) . . ?
C32 C27 C26 107.21(14) . . ?
C29 C28 C27 118.36(15) . . ?
C28 C29 C30 121.13(15) . . ?
C28 C29 N4 118.67(15) . . ?
C30 C29 N4 120.10(14) . . ?
C31 C30 C29 121.36(15) . . ?
C30 C31 C32 117.30(15) . . ?
C31 C32 N3 129.76(15) . . ?
C31 C32 C27 121.67(14) . . ?
N3 C32 C27 108.57(14) . . ?
N5 C33 C34 128.99(16) . . ?
N5 C33 C38 108.97(15) . . ?
C34 C33 C38 122.03(16) . . ?
C35 C34 C33 117.30(18) . . ?
C34 C35 C36 122.01(18) . . ?
C37 C36 C35 120.46(18) . . ?
C36 C37 C38 118.96(18) . . ?
C37 C38 C33 119.22(17) . . ?
C37 C38 C39 134.05(17) . . ?
C33 C38 C39 106.72(15) . . ?
C40 C39 C44 119.23(16) . . ?
C40 C39 C38 133.97(17) . . ?
C44 C39 C38 106.79(15) . . ?
C41 C40 C39 119.01(17) . . ?
C40 C41 C42 120.81(17) . . ?
C43 C42 C41 121.47(18) . . ?
C42 C43 C44 117.54(17) . . ?
N5 C44 C43 129.11(16) . . ?
N5 C44 C39 108.90(15) . . ?
C43 C44 C39 121.92(16) . . ?
N4 C45 C46 129.27(15) . . ?
N4 C45 C50 109.03(15) . . ?
C46 C45 C50 121.68(16) . . ?
C47 C46 C45 117.76(16) . . ?
C46 C47 C48 121.24(18) . . ?
C49 C48 C47 120.91(18) . . ?
C48 C49 C50 119.08(17) . . ?
C49 C50 C45 119.30(17) . . ?
C49 C50 C51 134.14(16) . . ?
C45 C50 C51 106.56(15) . . ?
C52 C51 C56 119.26(18) . . ?
C52 C51 C50 133.58(18) . . ?
C56 C51 C50 107.16(14) . . ?
C53 C52 C51 118.80(19) . . ?
C52 C53 C54 121.06(18) . . ?
C53 C54 C55 121.6(2) . . ?
C56 C55 C54 117.15(18) . . ?
C55 C56 N4 129.25(16) . . ?
C55 C56 C51 122.08(16) . . ?
N4 C56 C51 108.66(15) . . ?

_refine_diff_density_max         0.491
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.105



