# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_ng134
_database_code_depnum_ccdc_archive 'CCDC 2069434'
loop_
_audit_author_name
_audit_author_address
'Nikolai Korotkikh'
;The institute of Organic Chemistry, Kyiv
Ukraine
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        
'1-Tert-Butyl-3-phenyl-4-(2,4-difluorophenyl)-1,2,4-triazolium perchlorate'
_chemical_name_common            ?
_chemical_melting_point          388
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Cl F2 N3 O4'
_chemical_formula_weight         413.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.248(2)
_cell_length_b                   9.092(2)
_cell_length_c                   20.307(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.102(9)
_cell_angle_gamma                90
_cell_volume                     1891.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.251
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18531
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.007
_diffrn_reflns_theta_max         26.488
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3899
_reflns_number_gt                2549
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1148P)²+2.9087P] 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         3899
_refine_ls_number_parameters     274
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0761
_refine_ls_wR_factor_ref         0.2327
_refine_ls_wR_factor_gt          0.2023
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.003
_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
CL1A Cl 0.6248(3) 0.0956(4) 0.19603(15) 0.0396(8) Uani 0.669(9) 1 d D . P A 1
O1A O 0.6393(13) 0.2456(7) 0.2112(6) 0.274(9) Uani 0.669(9) 1 d D . P A 1
O2A O 0.5000(6) 0.0380(17) 0.1992(5) 0.247(10) Uani 0.669(9) 1 d D . P A 1
O3A O 0.7082(7) 0.0142(11) 0.2383(3) 0.136(5) Uani 0.669(9) 1 d D . P A 1
O4A O 0.6700(5) 0.0822(6) 0.13033(19) 0.0636(19) Uani 0.669(9) 1 d D . P A 1
CL1B Cl 0.6090(6) 0.1177(7) 0.1865(3) 0.0273(14) Uiso 0.331(9) 1 d D . P A 2
O1B O 0.592(3) 0.230(3) 0.1388(11) 0.31(2) Uiso 0.331(9) 1 d D . P A 2
O2B O 0.577(3) -0.0214(19) 0.1592(14) 0.32(2) Uiso 0.331(9) 1 d D . P A 2
O3B O 0.5213(14) 0.1455(18) 0.2370(6) 0.104(6) Uiso 0.331(9) 1 d D . P A 2
O4B O 0.7389(11) 0.115(4) 0.2120(14) 0.39(4) Uiso 0.331(9) 1 d D . P A 2
C3 C 0.9637(3) 0.7785(4) 0.05047(18) 0.0313(8) Uani 1 1 d . . . . .
C5 C 0.9031(4) 0.8610(4) 0.14604(19) 0.0372(9) Uani 1 1 d . . . . .
H5A H 0.853527 0.886323 0.182995 0.045 Uiso 1 1 calc R U . . .
C6 C 1.1262(4) 0.9506(5) 0.18704(19) 0.0397(10) Uani 1 1 d . . . . .
C7 C 1.2010(4) 1.0669(5) 0.1502(2) 0.0467(11) Uani 1 1 d . . . . .
H7A H 1.246002 1.020750 0.113819 0.070 Uiso 1 1 calc R U . . .
H7B H 1.139996 1.141405 0.132690 0.070 Uiso 1 1 calc R U . . .
H7C H 1.265289 1.113570 0.180422 0.070 Uiso 1 1 calc R U . . .
C8 C 1.2169(6) 0.8259(6) 0.2083(3) 0.0680(16) Uani 1 1 d . . . . .
H8A H 1.260790 0.787512 0.169827 0.102 Uiso 1 1 calc R U . . .
H8B H 1.282226 0.862436 0.240708 0.102 Uiso 1 1 calc R U . . .
H8C H 1.166026 0.747113 0.228065 0.102 Uiso 1 1 calc R U . . .
C9 C 1.0552(5) 1.0152(6) 0.2435(2) 0.0643(15) Uani 1 1 d . . . . .
H9A H 1.118396 1.058363 0.275299 0.096 Uiso 1 1 calc R U . . .
H9B H 0.995037 1.091622 0.226991 0.096 Uiso 1 1 calc R U . . .
H9C H 1.005782 0.937714 0.265037 0.096 Uiso 1 1 calc R U . . .
C10 C 0.7250(3) 0.7516(4) 0.07726(18) 0.0327(8) Uani 1 1 d . . . . .
C11 C 0.6530(4) 0.8296(4) 0.02995(18) 0.0349(9) Uani 1 1 d . . . . .
C12 C 0.5275(4) 0.7924(5) 0.0120(2) 0.0431(10) Uani 1 1 d . . . . .
H12A H 0.478853 0.844996 -0.021070 0.052 Uiso 1 1 calc R U . . .
C13 C 0.4760(4) 0.6750(5) 0.0442(2) 0.0452(11) Uani 1 1 d . . . . .
C14 C 0.5421(4) 0.5954(5) 0.0918(2) 0.0493(11) Uani 1 1 d . . . . .
H14A H 0.501521 0.514699 0.112647 0.059 Uiso 1 1 calc R U . . .
C15 C 0.6695(4) 0.6348(5) 0.1091(2) 0.0416(10) Uani 1 1 d . . . . .
H15A H 0.717724 0.582052 0.142207 0.050 Uiso 1 1 calc R U . . .
C18 C 0.9666(3) 0.7090(4) -0.01457(18) 0.0326(8) Uani 1 1 d . . . . .
C19 C 0.8748(4) 0.6060(4) -0.03607(18) 0.0343(8) Uani 1 1 d . . . . .
H19A H 0.804387 0.580889 -0.009069 0.041 Uiso 1 1 calc R U . . .
C20 C 0.8861(4) 0.5397(5) -0.09720(19) 0.0388(9) Uani 1 1 d . . . . .
H20A H 0.822110 0.470719 -0.112323 0.047 Uiso 1 1 calc R U . . .
C21 C 0.9891(4) 0.5730(5) -0.1360(2) 0.0431(10) Uani 1 1 d . . . . .
H21A H 0.996420 0.527384 -0.177746 0.052 Uiso 1 1 calc R U . . .
C22 C 1.0824(4) 0.6736(5) -0.1137(2) 0.0441(10) Uani 1 1 d . . . . .
H22A H 1.154527 0.695383 -0.140118 0.053 Uiso 1 1 calc R U . . .
C23 C 1.0713(4) 0.7424(5) -0.05374(19) 0.0392(9) Uani 1 1 d . . . . .
H23A H 1.134918 0.812350 -0.039142 0.047 Uiso 1 1 calc R U . . .
F16 F 0.7098(2) 0.9443(3) 0.00107(12) 0.0476(6) Uani 1 1 d . . . . .
F17 F 0.3520(2) 0.6353(4) 0.02726(16) 0.0689(9) Uani 1 1 d . . . . .
N1 N 1.0270(3) 0.8854(4) 0.13923(15) 0.0350(7) Uani 1 1 d . . . . .
N2 N 1.0680(3) 0.8354(4) 0.08006(15) 0.0358(8) Uani 1 1 d . . . . .
N4 N 0.8586(3) 0.7929(4) 0.09055(15) 0.0334(7) 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
CL1Aa O2A 1.385(4) . ?
CL1Aa O3A 1.400(4) . ?
CL1Aa O1A 1.405(5) . ?
CL1Aa O4A 1.433(4) . ?
CL1Bb O3B 1.410(5) . ?
CL1Bb O4B 1.412(5) . ?
CL1Bb O1B 1.414(5) . ?
CL1Bb O2B 1.415(5) . ?
C3 N2 1.313(5) . ?
C3 N4 1.380(5) . ?
C3 C18 1.466(5) . ?
C5 N1 1.300(5) . ?
C5 N4 1.351(5) . ?
C6 C9 1.500(6) . ?
C6 N1 1.502(5) . ?
C6 C7 1.519(6) . ?
C6 C8 1.519(6) . ?
C10 C15 1.376(6) . ?
C10 C11 1.385(5) . ?
C10 N4 1.435(5) . ?
C11 F16 1.340(5) . ?
C11 C12 1.366(5) . ?
C12 C13 1.369(6) . ?
C13 F17 1.353(4) . ?
C13 C14 1.367(6) . ?
C14 C15 1.387(6) . ?
C18 C19 1.386(5) . ?
C18 C23 1.393(5) . ?
C19 C20 1.389(5) . ?
C20 C21 1.374(6) . ?
C21 C22 1.387(6) . ?
C22 C23 1.378(6) . ?
N1 N2 1.365(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
O2Aa CL1Aa O3A 108.4(6) . . ?
O2Aa CL1Aa O1A 116.6(7) . . ?
O3Aa CL1Aa O1A 108.8(7) . . ?
O2Aa CL1Aa O4A 109.9(5) . . ?
O3Aa CL1Aa O4A 108.3(4) . . ?
O1Aa CL1Aa O4A 104.6(5) . . ?
O3Bb CL1Bb O4B 110.7(9) . . ?
O3Bb CL1Bb O1B 107.6(9) . . ?
O4Bb CL1Bb O1B 110.7(9) . . ?
O3Bb CL1Bb O2B 107.4(9) . . ?
O4Bb CL1Bb O2B 109.5(9) . . ?
O1Bb CL1Bb O2B 110.8(9) . . ?
N2 C3 N4 109.4(3) . . ?
N2 C3 C18 122.6(3) . . ?
N4 C3 C18 127.9(3) . . ?
N1 C5 N4 106.9(3) . . ?
C9 C6 N1 108.2(3) . . ?
C9 C6 C7 111.8(4) . . ?
N1 C6 C7 107.4(3) . . ?
C9 C6 C8 112.6(4) . . ?
N1 C6 C8 106.4(3) . . ?
C7 C6 C8 110.2(4) . . ?
C15 C10 C11 120.1(4) . . ?
C15 C10 N4 121.4(4) . . ?
C11 C10 N4 118.4(3) . . ?
F16 C11 C12 119.7(4) . . ?
F16 C11 C10 118.2(3) . . ?
C12 C11 C10 122.1(4) . . ?
C11 C12 C13 116.2(4) . . ?
F17 C13 C14 118.3(4) . . ?
F17 C13 C12 117.5(4) . . ?
C14 C13 C12 124.2(4) . . ?
C13 C14 C15 118.6(4) . . ?
C10 C15 C14 118.8(4) . . ?
C19 C18 C23 119.7(3) . . ?
C19 C18 C3 122.6(3) . . ?
C23 C18 C3 117.5(3) . . ?
C18 C19 C20 119.8(4) . . ?
C21 C20 C19 120.5(4) . . ?
C20 C21 C22 119.6(4) . . ?
C23 C22 C21 120.6(4) . . ?
C22 C23 C18 119.7(4) . . ?
C5 N1 N2 111.7(3) . . ?
C5 N1 C6 129.7(3) . . ?
N2 N1 C6 118.5(3) . . ?
C3 N2 N1 105.2(3) . . ?
C5 N4 C3 106.7(3) . . ?
C5 N4 C10 124.6(3) . . ?
C3 N4 C10 128.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 C10 C11 F16 178.8(3) . . . . ?
N4 C10 C11 F16 -3.0(5) . . . . ?
C15 C10 C11 C12 -1.7(6) . . . . ?
N4 C10 C11 C12 176.5(3) . . . . ?
F16 C11 C12 C13 -179.3(4) . . . . ?
C10 C11 C12 C13 1.2(6) . . . . ?
C11 C12 C13 F17 -179.7(4) . . . . ?
C11 C12 C13 C14 -0.4(7) . . . . ?
F17 C13 C14 C15 179.4(4) . . . . ?
C12 C13 C14 C15 0.1(7) . . . . ?
C11 C10 C15 C14 1.3(6) . . . . ?
N4 C10 C15 C14 -176.8(4) . . . . ?
C13 C14 C15 C10 -0.6(6) . . . . ?
N2 C3 C18 C19 156.6(4) . . . . ?
N4 C3 C18 C19 -21.8(6) . . . . ?
N2 C3 C18 C23 -19.2(5) . . . . ?
N4 C3 C18 C23 162.4(4) . . . . ?
C23 C18 C19 C20 -1.6(6) . . . . ?
C3 C18 C19 C20 -177.3(3) . . . . ?
C18 C19 C20 C21 1.4(6) . . . . ?
C19 C20 C21 C22 0.0(6) . . . . ?
C20 C21 C22 C23 -1.2(7) . . . . ?
C21 C22 C23 C18 1.0(6) . . . . ?
C19 C18 C23 C22 0.5(6) . . . . ?
C3 C18 C23 C22 176.4(4) . . . . ?
N4 C5 N1 N2 0.1(4) . . . . ?
N4 C5 N1 C6 -176.4(4) . . . . ?
C9 C6 N1 C5 -11.3(6) . . . . ?
C7 C6 N1 C5 -132.1(4) . . . . ?
C8 C6 N1 C5 109.9(5) . . . . ?
C9 C6 N1 N2 172.5(4) . . . . ?
C7 C6 N1 N2 51.6(5) . . . . ?
C8 C6 N1 N2 -66.4(5) . . . . ?
N4 C3 N2 N1 0.1(4) . . . . ?
C18 C3 N2 N1 -178.6(3) . . . . ?
C5 N1 N2 C3 -0.1(4) . . . . ?
C6 N1 N2 C3 176.8(3) . . . . ?
N1 C5 N4 C3 0.0(4) . . . . ?
N1 C5 N4 C10 -177.6(3) . . . . ?
N2 C3 N4 C5 0.0(4) . . . . ?
C18 C3 N4 C5 178.5(4) . . . . ?
N2 C3 N4 C10 177.4(4) . . . . ?
C18 C3 N4 C10 -4.0(6) . . . . ?
C15 C10 N4 C5 -73.4(5) . . . . ?
C11 C10 N4 C5 108.4(4) . . . . ?
C15 C10 N4 C3 109.5(5) . . . . ?
C11 C10 N4 C3 -68.6(5) . . . . ?

_refine_diff_density_max         0.719
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.085


_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_nk742
_database_code_depnum_ccdc_archive 'CCDC 2069437'
loop_
_audit_author_name
_audit_author_address
'Nikolai Korotkikh'
;The institute of Organic Chemistry, Kyiv
Ukraine
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 Cu F3 I N3'
_chemical_formula_weight         535.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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                   12.6541(13)
_cell_length_b                   19.843(2)
_cell_length_c                   18.004(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.426(3)
_cell_angle_gamma                90
_cell_volume                     4263.5(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_F_000             2096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.506
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13425
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.991
_diffrn_reflns_theta_max         25.354
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.935
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.935
_reflns_number_total             7289
_reflns_number_gt                4473
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0700P)²+0.7415P] 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         7289
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1435
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.010
_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
C1 C 0.9476(6) 0.1350(3) 0.4048(4) 0.0510(17) Uani 1 1 d . . . . .
C2 C 0.9993(6) 0.1322(3) 0.2967(4) 0.0524(17) Uani 1 1 d . . . . .
C3 C 0.8278(6) 0.0654(4) 0.2943(3) 0.0489(17) Uani 1 1 d . . . . .
C4 C 0.7286(7) 0.0907(4) 0.2423(4) 0.064(2) Uani 1 1 d . . . . .
C5 C 0.6422(7) 0.0444(6) 0.2075(5) 0.085(3) Uani 1 1 d . . . . .
H5 H 0.574176 0.059909 0.173054 0.102 Uiso 1 1 calc R U . . .
C6 C 0.6565(8) -0.0230(6) 0.2233(5) 0.087(3) Uani 1 1 d . . . . .
H6 H 0.599679 -0.053144 0.197981 0.105 Uiso 1 1 calc R U . . .
C7 C 0.7536(7) -0.0460(4) 0.2759(5) 0.076(2) Uani 1 1 d . . . . .
H7 H 0.762619 -0.091835 0.286814 0.091 Uiso 1 1 calc R U . . .
C8 C 0.8393(6) -0.0019(3) 0.3134(4) 0.0584(19) Uani 1 1 d . . . . .
H8 H 0.904236 -0.017556 0.351370 0.070 Uiso 1 1 calc R U . . .
C9 C 0.7110(10) 0.1625(7) 0.2232(7) 0.113(4) Uani 1 1 d . . . . .
C10 C 1.1035(7) 0.2149(4) 0.4798(4) 0.069(2) Uani 1 1 d . . . . .
C11 C 1.0427(9) 0.2817(4) 0.4696(5) 0.103(3) Uani 1 1 d . . . . .
H11A H 1.081163 0.311160 0.512349 0.154 Uiso 1 1 calc R U . . .
H11B H 1.040728 0.301870 0.420689 0.154 Uiso 1 1 calc R U . . .
H11C H 0.967482 0.274517 0.469260 0.154 Uiso 1 1 calc R U . . .
C12 C 1.1043(8) 0.1806(4) 0.5558(4) 0.086(3) Uani 1 1 d . . . . .
H12A H 1.144714 0.208050 0.600029 0.129 Uiso 1 1 calc R U . . .
H12B H 1.028710 0.174685 0.555101 0.129 Uiso 1 1 calc R U . . .
H12C H 1.140092 0.137410 0.560078 0.129 Uiso 1 1 calc R U . . .
C13 C 1.2248(8) 0.2204(6) 0.4791(5) 0.121(4) Uani 1 1 d . . . . .
H13A H 1.267844 0.248283 0.522137 0.182 Uiso 1 1 calc R U . . .
H13B H 1.257615 0.176332 0.484431 0.182 Uiso 1 1 calc R U . . .
H13C H 1.224295 0.240144 0.430301 0.182 Uiso 1 1 calc R U . . .
C14 C 1.0002(6) 0.1175(4) 0.2169(4) 0.0545(18) Uani 1 1 d . . . . .
C15 C 0.9699(7) 0.0562(5) 0.1809(4) 0.075(2) Uani 1 1 d . . . . .
H15 H 0.948935 0.021153 0.207278 0.090 Uiso 1 1 calc R U . . .
C16 C 0.9708(8) 0.0471(5) 0.1040(5) 0.088(3) Uani 1 1 d . . . . .
H16 H 0.953630 0.005153 0.079898 0.106 Uiso 1 1 calc R U . . .
C17 C 0.9970(8) 0.0999(6) 0.0644(5) 0.098(3) Uani 1 1 d . . . . .
H17 H 0.992591 0.094631 0.012112 0.118 Uiso 1 1 calc R U . . .
C18 C 1.0291(9) 0.1595(6) 0.1008(6) 0.107(3) Uani 1 1 d . . . . .
H18 H 1.049691 0.194628 0.074218 0.128 Uiso 1 1 calc R U . . .
C19 C 1.0315(8) 0.1686(5) 0.1778(5) 0.083(3) Uani 1 1 d . . . . .
H19 H 1.054420 0.209721 0.202804 0.099 Uiso 1 1 calc R U . . .
C20 C 0.8157(6) 0.0949(3) 0.7222(4) 0.0539(18) Uani 1 1 d . . . . .
C21 C 0.7776(6) 0.0553(4) 0.8283(4) 0.0549(18) Uani 1 1 d . . . . .
C22 C 0.6587(6) 0.0150(3) 0.6936(4) 0.0498(17) Uani 1 1 d . . . . .
C23 C 0.5527(7) 0.0449(4) 0.6637(5) 0.067(2) Uani 1 1 d . . . . .
C24 C 0.4685(8) 0.0076(6) 0.6119(6) 0.098(3) Uani 1 1 d . . . . .
H24 H 0.397170 0.026190 0.591656 0.118 Uiso 1 1 calc R U . . .
C25 C 0.4861(10) -0.0544(7) 0.5896(6) 0.110(4) Uani 1 1 d . . . . .
H25 H 0.426881 -0.078171 0.554832 0.132 Uiso 1 1 calc R U . . .
C26 C 0.5898(10) -0.0834(5) 0.6173(6) 0.094(3) Uani 1 1 d . . . . .
H26 H 0.601380 -0.126231 0.600588 0.113 Uiso 1 1 calc R U . . .
C27 C 0.6785(7) -0.0483(4) 0.6709(4) 0.065(2) Uani 1 1 d . . . . .
H27 H 0.749412 -0.067547 0.690765 0.077 Uiso 1 1 calc R U . . .
C28 C 0.5280(8) 0.1136(5) 0.6830(8) 0.096(3) Uani 1 1 d . . . . .
C29 C 0.9699(9) 0.1744(5) 0.8019(5) 0.097(3) Uani 1 1 d . . . . .
C30 C 1.0108(9) 0.1760(6) 0.7344(6) 0.125(4) Uani 1 1 d . . . . .
H30A H 1.034124 0.131585 0.725340 0.188 Uiso 1 1 calc R U . . .
H30B H 0.951777 0.191008 0.688397 0.188 Uiso 1 1 calc R U . . .
H30C H 1.073159 0.206359 0.745445 0.188 Uiso 1 1 calc R U . . .
C31 C 1.0811(11) 0.1463(7) 0.8706(7) 0.181(7) Uani 1 1 d . . . . .
H31A H 1.104842 0.104806 0.853617 0.272 Uiso 1 1 calc R U . . .
H31B H 1.140195 0.178955 0.880696 0.272 Uiso 1 1 calc R U . . .
H31C H 1.063835 0.138527 0.917933 0.272 Uiso 1 1 calc R U . . .
C32 C 0.9329(15) 0.2337(7) 0.8236(16) 0.333(16) Uani 1 1 d . . . . .
H32A H 0.908644 0.225908 0.868033 0.499 Uiso 1 1 calc R U . . .
H32B H 0.992704 0.266027 0.837463 0.499 Uiso 1 1 calc R U . . .
H32C H 0.871321 0.250676 0.780415 0.499 Uiso 1 1 calc R U . . .
C33 C 0.7266(6) 0.0178(4) 0.8772(4) 0.060(2) Uani 1 1 d . . . . .
C34 C 0.7030(8) 0.0504(5) 0.9376(5) 0.093(3) Uani 1 1 d . . . . .
H34 H 0.715911 0.096471 0.944248 0.112 Uiso 1 1 calc R U . . .
C35 C 0.6610(9) 0.0165(7) 0.9880(6) 0.114(4) Uani 1 1 d . . . . .
H35 H 0.643340 0.039716 1.027207 0.137 Uiso 1 1 calc R U . . .
C36 C 0.6453(8) -0.0513(8) 0.9802(7) 0.112(4) Uani 1 1 d . . . . .
H36 H 0.618729 -0.074662 1.015202 0.135 Uiso 1 1 calc R U . . .
C37 C 0.6679(8) -0.0849(6) 0.9221(7) 0.107(4) Uani 1 1 d . . . . .
H37 H 0.655383 -0.131130 0.916684 0.128 Uiso 1 1 calc R U . . .
C38 C 0.7101(7) -0.0507(4) 0.8700(5) 0.077(2) Uani 1 1 d . . . . .
H38 H 0.726829 -0.074181 0.830668 0.093 Uiso 1 1 calc R U . . .
CU1 Cu 0.86327(7) 0.11988(5) 0.47519(5) 0.0593(3) Uani 1 1 d . . . . .
CU2 Cu 0.80654(7) 0.10517(5) 0.61366(5) 0.0572(3) Uani 1 1 d . . . . .
F1 F 0.7725(7) 0.1866(4) 0.1847(6) 0.187(4) Uani 1 1 d . . . . .
F2 F 0.6056(5) 0.1771(3) 0.1803(4) 0.137(2) Uani 1 1 d . . . . .
F3 F 0.7308(8) 0.2010(3) 0.2860(5) 0.197(5) Uani 1 1 d . . . . .
F4 F 0.5820(6) 0.1606(3) 0.6573(5) 0.164(3) Uani 1 1 d . . . . .
F5 F 0.5560(5) 0.1243(3) 0.7596(5) 0.136(2) Uani 1 1 d . . . . .
F6 F 0.4218(5) 0.1312(3) 0.6553(4) 0.144(3) Uani 1 1 d . . . . .
I1 I 0.74261(5) 0.20646(3) 0.51950(3) 0.0717(2) Uani 1 1 d . . . . .
I2 I 0.84448(4) 0.00457(2) 0.53540(3) 0.05813(18) Uani 1 1 d . . . . .
N1 N 0.9212(4) 0.1104(3) 0.3299(3) 0.0457(13) Uani 1 1 d . . . . .
N2 N 1.0399(5) 0.1710(3) 0.4116(3) 0.0572(15) Uani 1 1 d . . . . .
N3 N 1.0718(5) 0.1702(3) 0.3465(3) 0.0604(16) Uani 1 1 d . . . . .
N4 N 0.7485(4) 0.0532(3) 0.7470(3) 0.0496(14) Uani 1 1 d . . . . .
N5 N 0.8818(5) 0.1217(3) 0.7904(3) 0.0652(17) Uani 1 1 d . . . . .
N6 N 0.8590(6) 0.0987(3) 0.8556(3) 0.0711(18) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.339(8) . ?
C1 N1 1.367(8) . ?
C1 CU1 1.933(7) . ?
C2 N3 1.292(8) . ?
C2 N1 1.383(8) . ?
C2 C14 1.471(9) . ?
C3 C8 1.374(9) . ?
C3 C4 1.386(9) . ?
C3 N1 1.451(8) . ?
C4 C5 1.406(11) . ?
C4 C9 1.465(14) . ?
C5 C6 1.367(13) . ?
C6 C7 1.356(11) . ?
C7 C8 1.383(10) . ?
C9 F1 1.293(14) . ?
C9 F3 1.318(13) . ?
C9 F2 1.332(11) . ?
C10 N2 1.503(9) . ?
C10 C11 1.513(11) . ?
C10 C12 1.525(10) . ?
C10 C13 1.543(12) . ?
C14 C19 1.367(10) . ?
C14 C15 1.371(10) . ?
C15 C16 1.400(10) . ?
C16 C17 1.370(12) . ?
C17 C18 1.347(13) . ?
C18 C19 1.388(11) . ?
C20 N5 1.344(8) . ?
C20 N4 1.364(8) . ?
C20 CU2 1.930(6) . ?
C21 N6 1.306(8) . ?
C21 N4 1.386(8) . ?
C21 C33 1.458(9) . ?
C22 C27 1.370(9) . ?
C22 C23 1.400(10) . ?
C22 N4 1.436(8) . ?
C23 C24 1.375(12) . ?
C23 C28 1.466(12) . ?
C24 C25 1.335(14) . ?
C25 C26 1.367(14) . ?
C26 C27 1.398(11) . ?
C28 F6 1.315(10) . ?
C28 F5 1.322(12) . ?
C28 F4 1.327(11) . ?
C29 C32 1.371(16) . ?
C29 C30 1.471(12) . ?
C29 N5 1.492(9) . ?
C29 C31 1.632(15) . ?
C33 C38 1.374(10) . ?
C33 C34 1.380(11) . ?
C34 C35 1.370(13) . ?
C35 C36 1.361(15) . ?
C36 C37 1.349(15) . ?
C37 C38 1.400(12) . ?
CU1 I2 2.5766(10) . ?
CU1 I1 2.5942(11) . ?
CU1 CU2 2.8295(13) . ?
CU2 I2 2.5790(10) . ?
CU2 I1 2.5800(10) . ?
N2 N3 1.360(7) . ?
N5 N6 1.377(7) . ?

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
N2 C1 N1 101.5(6) . . ?
N2 C1 CU1 132.7(5) . . ?
N1 C1 CU1 125.8(5) . . ?
N3 C2 N1 109.1(6) . . ?
N3 C2 C14 124.0(7) . . ?
N1 C2 C14 126.8(6) . . ?
C8 C3 C4 121.3(7) . . ?
C8 C3 N1 119.0(6) . . ?
C4 C3 N1 119.8(7) . . ?
C3 C4 C5 117.3(8) . . ?
C3 C4 C9 123.0(8) . . ?
C5 C4 C9 119.7(8) . . ?
C6 C5 C4 121.1(8) . . ?
C7 C6 C5 120.0(8) . . ?
C6 C7 C8 120.6(8) . . ?
C3 C8 C7 119.4(7) . . ?
F1 C9 F3 105.6(13) . . ?
F1 C9 F2 105.9(9) . . ?
F3 C9 F2 103.8(10) . . ?
F1 C9 C4 114.4(11) . . ?
F3 C9 C4 113.0(9) . . ?
F2 C9 C4 113.1(11) . . ?
N2 C10 C11 107.2(6) . . ?
N2 C10 C12 108.4(6) . . ?
C11 C10 C12 110.6(8) . . ?
N2 C10 C13 107.3(7) . . ?
C11 C10 C13 113.8(8) . . ?
C12 C10 C13 109.2(7) . . ?
C19 C14 C15 119.9(7) . . ?
C19 C14 C2 117.0(7) . . ?
C15 C14 C2 123.1(7) . . ?
C14 C15 C16 119.3(8) . . ?
C17 C16 C15 119.9(9) . . ?
C18 C17 C16 120.3(9) . . ?
C17 C18 C19 120.2(9) . . ?
C14 C19 C18 120.2(9) . . ?
N5 C20 N4 102.0(5) . . ?
N5 C20 CU2 133.9(5) . . ?
N4 C20 CU2 124.2(5) . . ?
N6 C21 N4 108.5(6) . . ?
N6 C21 C33 124.2(6) . . ?
N4 C21 C33 127.4(6) . . ?
C27 C22 C23 121.4(7) . . ?
C27 C22 N4 120.0(6) . . ?
C23 C22 N4 118.5(6) . . ?
C24 C23 C22 117.4(8) . . ?
C24 C23 C28 118.9(9) . . ?
C22 C23 C28 123.7(7) . . ?
C25 C24 C23 122.1(10) . . ?
C24 C25 C26 120.9(9) . . ?
C25 C26 C27 119.7(9) . . ?
C22 C27 C26 118.5(8) . . ?
F6 C28 F5 103.8(10) . . ?
F6 C28 F4 105.1(9) . . ?
F5 C28 F4 105.1(10) . . ?
F6 C28 C23 115.3(9) . . ?
F5 C28 C23 113.2(9) . . ?
F4 C28 C23 113.2(10) . . ?
C32 C29 C30 117.6(13) . . ?
C32 C29 N5 109.3(10) . . ?
C30 C29 N5 110.6(7) . . ?
C32 C29 C31 111.6(13) . . ?
C30 C29 C31 100.5(10) . . ?
N5 C29 C31 106.4(8) . . ?
C38 C33 C34 118.1(8) . . ?
C38 C33 C21 122.2(8) . . ?
C34 C33 C21 119.4(8) . . ?
C35 C34 C33 121.7(10) . . ?
C36 C35 C34 119.5(11) . . ?
C37 C36 C35 120.5(11) . . ?
C36 C37 C38 120.4(11) . . ?
C33 C38 C37 119.8(9) . . ?
C1 CU1 I2 124.2(2) . . ?
C1 CU1 I1 127.5(2) . . ?
I2 CU1 I1 108.22(4) . . ?
C1 CU1 CU2 162.0(2) . . ?
I2 CU1 CU2 56.75(3) . . ?
I1 CU1 CU2 56.61(3) . . ?
C20 CU2 I2 120.8(2) . . ?
C20 CU2 I1 130.4(2) . . ?
I2 CU2 I1 108.58(3) . . ?
C20 CU2 CU1 162.9(2) . . ?
I2 CU2 CU1 56.67(3) . . ?
I1 CU2 CU1 57.09(3) . . ?
CU2 I1 CU1 66.30(3) . . ?
CU1 I2 CU2 66.57(3) . . ?
C1 N1 C2 109.8(6) . . ?
C1 N1 C3 123.5(6) . . ?
C2 N1 C3 126.6(5) . . ?
C1 N2 N3 114.5(5) . . ?
C1 N2 C10 126.7(6) . . ?
N3 N2 C10 118.6(6) . . ?
C2 N3 N2 105.0(6) . . ?
C20 N4 C21 110.6(5) . . ?
C20 N4 C22 122.8(5) . . ?
C21 N4 C22 126.6(6) . . ?
C20 N5 N6 113.9(5) . . ?
C20 N5 C29 127.9(6) . . ?
N6 N5 C29 118.2(6) . . ?
C21 N6 N5 105.1(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C3 C4 C5 -2.8(10) . . . . ?
N1 C3 C4 C5 177.8(6) . . . . ?
C8 C3 C4 C9 177.0(9) . . . . ?
N1 C3 C4 C9 -2.3(12) . . . . ?
C3 C4 C5 C6 -1.1(12) . . . . ?
C9 C4 C5 C6 179.1(10) . . . . ?
C4 C5 C6 C7 2.8(14) . . . . ?
C5 C6 C7 C8 -0.6(14) . . . . ?
C4 C3 C8 C7 4.9(11) . . . . ?
N1 C3 C8 C7 -175.7(6) . . . . ?
C6 C7 C8 C3 -3.2(12) . . . . ?
C3 C4 C9 F1 66.8(14) . . . . ?
C5 C4 C9 F1 -113.4(12) . . . . ?
C3 C4 C9 F3 -54.2(15) . . . . ?
C5 C4 C9 F3 125.6(11) . . . . ?
C3 C4 C9 F2 -171.8(8) . . . . ?
C5 C4 C9 F2 8.0(15) . . . . ?
N3 C2 C14 C19 -36.7(11) . . . . ?
N1 C2 C14 C19 140.8(8) . . . . ?
N3 C2 C14 C15 144.3(8) . . . . ?
N1 C2 C14 C15 -38.2(11) . . . . ?
C19 C14 C15 C16 -0.4(12) . . . . ?
C2 C14 C15 C16 178.6(8) . . . . ?
C14 C15 C16 C17 -2.9(13) . . . . ?
C15 C16 C17 C18 4.4(15) . . . . ?
C16 C17 C18 C19 -2.6(17) . . . . ?
C15 C14 C19 C18 2.1(14) . . . . ?
C2 C14 C19 C18 -176.9(8) . . . . ?
C17 C18 C19 C14 -0.7(16) . . . . ?
C27 C22 C23 C24 1.3(11) . . . . ?
N4 C22 C23 C24 179.2(7) . . . . ?
C27 C22 C23 C28 -177.1(9) . . . . ?
N4 C22 C23 C28 0.7(12) . . . . ?
C22 C23 C24 C25 -0.8(14) . . . . ?
C28 C23 C24 C25 177.8(10) . . . . ?
C23 C24 C25 C26 -0.6(17) . . . . ?
C24 C25 C26 C27 1.3(16) . . . . ?
C23 C22 C27 C26 -0.6(11) . . . . ?
N4 C22 C27 C26 -178.4(7) . . . . ?
C25 C26 C27 C22 -0.7(13) . . . . ?
C24 C23 C28 F6 7.5(15) . . . . ?
C22 C23 C28 F6 -174.1(8) . . . . ?
C24 C23 C28 F5 126.8(9) . . . . ?
C22 C23 C28 F5 -54.7(13) . . . . ?
C24 C23 C28 F4 -113.7(10) . . . . ?
C22 C23 C28 F4 64.8(13) . . . . ?
N6 C21 C33 C38 -131.5(9) . . . . ?
N4 C21 C33 C38 50.2(11) . . . . ?
N6 C21 C33 C34 42.5(11) . . . . ?
N4 C21 C33 C34 -135.8(8) . . . . ?
C38 C33 C34 C35 -2.0(14) . . . . ?
C21 C33 C34 C35 -176.2(9) . . . . ?
C33 C34 C35 C36 2.1(16) . . . . ?
C34 C35 C36 C37 -1.8(17) . . . . ?
C35 C36 C37 C38 1.3(16) . . . . ?
C34 C33 C38 C37 1.5(12) . . . . ?
C21 C33 C38 C37 175.6(7) . . . . ?
C36 C37 C38 C33 -1.2(14) . . . . ?
N2 C1 N1 C2 0.9(7) . . . . ?
CU1 C1 N1 C2 179.2(5) . . . . ?
N2 C1 N1 C3 177.7(5) . . . . ?
CU1 C1 N1 C3 -4.0(8) . . . . ?
N3 C2 N1 C1 -1.4(8) . . . . ?
C14 C2 N1 C1 -179.2(6) . . . . ?
N3 C2 N1 C3 -178.2(6) . . . . ?
C14 C2 N1 C3 4.0(11) . . . . ?
C8 C3 N1 C1 -78.9(8) . . . . ?
C4 C3 N1 C1 100.5(7) . . . . ?
C8 C3 N1 C2 97.4(8) . . . . ?
C4 C3 N1 C2 -83.2(8) . . . . ?
N1 C1 N2 N3 0.0(7) . . . . ?
CU1 C1 N2 N3 -178.2(5) . . . . ?
N1 C1 N2 C10 174.9(6) . . . . ?
CU1 C1 N2 C10 -3.3(11) . . . . ?
C11 C10 N2 C1 -81.5(9) . . . . ?
C12 C10 N2 C1 38.0(10) . . . . ?
C13 C10 N2 C1 155.8(7) . . . . ?
C11 C10 N2 N3 93.3(8) . . . . ?
C12 C10 N2 N3 -147.3(7) . . . . ?
C13 C10 N2 N3 -29.4(9) . . . . ?
N1 C2 N3 N2 1.3(7) . . . . ?
C14 C2 N3 N2 179.2(6) . . . . ?
C1 N2 N3 C2 -0.8(8) . . . . ?
C10 N2 N3 C2 -176.2(6) . . . . ?
N5 C20 N4 C21 -1.2(8) . . . . ?
CU2 C20 N4 C21 178.2(5) . . . . ?
N5 C20 N4 C22 177.0(6) . . . . ?
CU2 C20 N4 C22 -3.6(10) . . . . ?
N6 C21 N4 C20 2.0(8) . . . . ?
C33 C21 N4 C20 -179.5(7) . . . . ?
N6 C21 N4 C22 -176.2(6) . . . . ?
C33 C21 N4 C22 2.3(12) . . . . ?
C27 C22 N4 C20 89.4(8) . . . . ?
C23 C22 N4 C20 -88.5(8) . . . . ?
C27 C22 N4 C21 -92.7(9) . . . . ?
C23 C22 N4 C21 89.4(8) . . . . ?
N4 C20 N5 N6 0.1(8) . . . . ?
CU2 C20 N5 N6 -179.2(6) . . . . ?
N4 C20 N5 C29 -176.6(8) . . . . ?
CU2 C20 N5 C29 4.1(13) . . . . ?
C32 C29 N5 C20 107.9(15) . . . . ?
C30 C29 N5 C20 -23.2(14) . . . . ?
C31 C29 N5 C20 -131.4(9) . . . . ?
C32 C29 N5 N6 -68.7(16) . . . . ?
C30 C29 N5 N6 160.3(8) . . . . ?
C31 C29 N5 N6 52.0(11) . . . . ?
N4 C21 N6 N5 -1.8(8) . . . . ?
C33 C21 N6 N5 179.7(7) . . . . ?
C20 N5 N6 C21 1.1(9) . . . . ?
C29 N5 N6 C21 178.1(8) . . . . ?

_refine_diff_density_max         0.936
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_nk785
_database_code_depnum_ccdc_archive 'CCDC 2069438'
loop_
_audit_author_name
_audit_author_address
'Nikolai Korotkikh'
;The institute of Organic Chemistry, Kyiv
Ukraine
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 Cu F2 I N3'
_chemical_formula_weight         503.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.4747(2)
_cell_length_b                   16.5680(4)
_cell_length_c                   23.0336(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3997.36(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_F_000             1968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    2.660
_shelx_estimated_absorpt_T_min   0.431
_shelx_estimated_absorpt_T_max   0.534
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25162
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.459
_diffrn_reflns_theta_max         25.890
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3878
_reflns_number_gt                3279
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0697P)²+5.7818P] 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         3878
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.010
_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
CU1 Cu 0.53107(5) 0.03036(3) 0.45087(2) 0.02755(16) Uani 1 1 d . . . . .
F1 F 0.5928(3) -0.10164(16) 0.26777(12) 0.0375(6) Uani 1 1 d . . . . .
F2 F 0.2429(3) -0.25456(19) 0.33047(18) 0.0706(11) Uani 1 1 d . . . . .
I1 I 0.34131(3) 0.08975(2) 0.51072(2) 0.03735(14) Uani 1 1 d . . . . .
N1 N 0.5023(3) 0.0346(2) 0.32490(14) 0.0220(7) Uani 1 1 d . . . . .
N2 N 0.5986(3) 0.14091(19) 0.35101(14) 0.0229(7) Uani 1 1 d . . . . .
N3 N 0.5829(3) 0.1480(2) 0.29128(14) 0.0264(8) Uani 1 1 d . . . . .
C1 C 0.5497(4) 0.0737(2) 0.37326(17) 0.0214(8) Uani 1 1 d . . . . .
C2 C 0.5243(4) 0.0815(2) 0.27637(18) 0.0239(9) Uani 1 1 d . . . . .
C3 C 0.4382(4) -0.0416(2) 0.32787(17) 0.0221(8) Uani 1 1 d . . . . .
C4 C 0.4837(4) -0.1084(3) 0.29883(18) 0.0268(9) Uani 1 1 d . . . . .
C5 C 0.4196(4) -0.1808(3) 0.2984(2) 0.0343(10) Uani 1 1 d . . . . .
H5 H 0.449932 -0.226076 0.277194 0.041 Uiso 1 1 calc R U . . .
C6 C 0.3089(5) -0.1841(3) 0.3306(2) 0.0408(12) Uani 1 1 d . . . . .
C7 C 0.2626(5) -0.1211(3) 0.3621(2) 0.0435(12) Uani 1 1 d . . . . .
H7 H 0.187275 -0.126726 0.384674 0.052 Uiso 1 1 calc R U . . .
C8 C 0.3283(4) -0.0482(3) 0.3604(2) 0.0288(10) Uani 1 1 d . . . . .
H8 H 0.297473 -0.003073 0.381554 0.035 Uiso 1 1 calc R U . . .
C9 C 0.4901(4) 0.0610(3) 0.21612(18) 0.0278(9) Uani 1 1 d . . . . .
C10 C 0.5714(5) 0.0848(3) 0.17187(19) 0.0323(10) Uani 1 1 d . . . . .
H10 H 0.647019 0.113951 0.180800 0.039 Uiso 1 1 calc R U . . .
C11 C 0.5430(5) 0.0664(3) 0.1148(2) 0.0402(12) Uani 1 1 d . . . . .
H11 H 0.597681 0.084377 0.084567 0.048 Uiso 1 1 calc R U . . .
C12 C 0.4348(5) 0.0219(3) 0.1016(2) 0.0405(12) Uani 1 1 d . . . . .
H12 H 0.417602 0.007224 0.062545 0.049 Uiso 1 1 calc R U . . .
C13 C 0.3520(4) -0.0012(3) 0.1452(2) 0.0358(11) Uani 1 1 d . . . . .
H13 H 0.276876 -0.030711 0.135921 0.043 Uiso 1 1 calc R U . . .
C14 C 0.3784(4) 0.0186(3) 0.20276(19) 0.0314(10) Uani 1 1 d . . . . .
H14 H 0.320915 0.003459 0.232737 0.038 Uiso 1 1 calc R U . . .
C15 C 0.6577(4) 0.2109(2) 0.38230(19) 0.0253(9) Uani 1 1 d . . . . .
C16 C 0.5591(5) 0.2783(3) 0.3847(2) 0.0404(12) Uani 1 1 d . . . . .
H16A H 0.595273 0.324935 0.405003 0.061 Uiso 1 1 calc R U . . .
H16B H 0.535199 0.293904 0.345147 0.061 Uiso 1 1 calc R U . . .
H16C H 0.483216 0.259282 0.405548 0.061 Uiso 1 1 calc R U . . .
C17 C 0.7762(4) 0.2365(3) 0.3487(2) 0.0385(11) Uani 1 1 d . . . . .
H17A H 0.816606 0.282364 0.368388 0.058 Uiso 1 1 calc R U . . .
H17B H 0.836414 0.191353 0.346927 0.058 Uiso 1 1 calc R U . . .
H17C H 0.751814 0.252413 0.309269 0.058 Uiso 1 1 calc R U . . .
C18 C 0.6946(5) 0.1844(3) 0.4435(2) 0.0361(11) Uani 1 1 d . . . . .
H18A H 0.733336 0.229933 0.464240 0.054 Uiso 1 1 calc R U . . .
H18B H 0.618205 0.166437 0.464382 0.054 Uiso 1 1 calc R U . . .
H18C H 0.756025 0.139920 0.441247 0.054 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
CU1 C1 1.936(4) . ?
CU1 I1 2.5553(6) 5_656 ?
CU1 CU1 2.5607(10) 5_656 ?
CU1 I1 2.6115(6) . ?
F1 C4 1.353(5) . ?
F2 C6 1.357(5) . ?
I1 CU1 2.5552(6) 5_656 ?
N1 C1 1.381(5) . ?
N1 C2 1.380(5) . ?
N1 C3 1.432(5) . ?
N2 C1 1.329(5) . ?
N2 N3 1.391(5) . ?
N2 C15 1.500(5) . ?
N3 C2 1.307(5) . ?
C2 C9 1.473(6) . ?
C3 C8 1.377(6) . ?
C3 C4 1.378(6) . ?
C4 C5 1.376(6) . ?
C5 C6 1.377(7) . ?
C6 C7 1.360(7) . ?
C7 C8 1.390(6) . ?
C9 C10 1.386(6) . ?
C9 C14 1.399(6) . ?
C10 C11 1.381(7) . ?
C11 C12 1.386(7) . ?
C12 C13 1.380(7) . ?
C13 C14 1.394(6) . ?
C15 C16 1.521(6) . ?
C15 C17 1.523(6) . ?
C15 C18 1.527(6) . ?

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 CU1 I1 123.76(12) . 5_656 ?
C1 CU1 CU1 170.82(12) . 5_656 ?
I1 CU1 CU1 61.39(2) 5_656 5_656 ?
C1 CU1 I1 115.11(12) . . ?
I1 CU1 I1 120.59(2) 5_656 . ?
CU1 CU1 I1 59.20(2) 5_656 . ?
CU1 I1 CU1 59.41(2) 5_656 . ?
C1 N1 C2 109.3(3) . . ?
C1 N1 C3 122.9(3) . . ?
C2 N1 C3 127.8(3) . . ?
C1 N2 N3 114.0(3) . . ?
C1 N2 C15 128.5(3) . . ?
N3 N2 C15 117.3(3) . . ?
C2 N3 N2 104.2(3) . . ?
N2 C1 N1 102.7(3) . . ?
N2 C1 CU1 134.9(3) . . ?
N1 C1 CU1 122.3(3) . . ?
N3 C2 N1 109.8(4) . . ?
N3 C2 C9 123.7(4) . . ?
N1 C2 C9 126.4(4) . . ?
C8 C3 C4 119.3(4) . . ?
C8 C3 N1 119.2(4) . . ?
C4 C3 N1 121.5(4) . . ?
F1 C4 C5 118.8(4) . . ?
F1 C4 C3 118.9(4) . . ?
C5 C4 C3 122.3(4) . . ?
C4 C5 C6 116.2(4) . . ?
F2 C6 C7 118.7(4) . . ?
F2 C6 C5 117.5(4) . . ?
C7 C6 C5 123.8(4) . . ?
C6 C7 C8 118.3(4) . . ?
C3 C8 C7 119.9(4) . . ?
C10 C9 C14 119.7(4) . . ?
C10 C9 C2 118.6(4) . . ?
C14 C9 C2 121.7(4) . . ?
C11 C10 C9 120.3(5) . . ?
C10 C11 C12 120.1(5) . . ?
C13 C12 C11 120.2(4) . . ?
C12 C13 C14 120.0(4) . . ?
C9 C14 C13 119.6(4) . . ?
N2 C15 C16 107.7(3) . . ?
N2 C15 C17 107.9(3) . . ?
C16 C15 C17 111.6(4) . . ?
N2 C15 C18 109.0(3) . . ?
C16 C15 C18 110.4(4) . . ?
C17 C15 C18 110.0(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 N3 C2 -1.3(4) . . . . ?
C15 N2 N3 C2 -176.7(3) . . . . ?
N3 N2 C1 N1 1.3(4) . . . . ?
C15 N2 C1 N1 176.1(3) . . . . ?
N3 N2 C1 CU1 -176.2(3) . . . . ?
C15 N2 C1 CU1 -1.3(7) . . . . ?
C2 N1 C1 N2 -0.7(4) . . . . ?
C3 N1 C1 N2 -179.2(3) . . . . ?
C2 N1 C1 CU1 177.1(3) . . . . ?
C3 N1 C1 CU1 -1.4(5) . . . . ?
N2 N3 C2 N1 0.7(4) . . . . ?
N2 N3 C2 C9 -178.4(4) . . . . ?
C1 N1 C2 N3 0.0(5) . . . . ?
C3 N1 C2 N3 178.4(4) . . . . ?
C1 N1 C2 C9 179.1(4) . . . . ?
C3 N1 C2 C9 -2.5(6) . . . . ?
C1 N1 C3 C8 60.1(5) . . . . ?
C2 N1 C3 C8 -118.1(5) . . . . ?
C1 N1 C3 C4 -120.1(4) . . . . ?
C2 N1 C3 C4 61.7(6) . . . . ?
C8 C3 C4 F1 -179.0(4) . . . . ?
N1 C3 C4 F1 1.2(6) . . . . ?
C8 C3 C4 C5 3.6(7) . . . . ?
N1 C3 C4 C5 -176.2(4) . . . . ?
F1 C4 C5 C6 -179.7(4) . . . . ?
C3 C4 C5 C6 -2.3(7) . . . . ?
C4 C5 C6 F2 179.3(5) . . . . ?
C4 C5 C6 C7 -0.6(8) . . . . ?
F2 C6 C7 C8 -177.8(5) . . . . ?
C5 C6 C7 C8 2.2(9) . . . . ?
C4 C3 C8 C7 -2.0(7) . . . . ?
N1 C3 C8 C7 177.8(4) . . . . ?
C6 C7 C8 C3 -0.8(8) . . . . ?
N3 C2 C9 C10 34.6(6) . . . . ?
N1 C2 C9 C10 -144.4(4) . . . . ?
N3 C2 C9 C14 -145.3(4) . . . . ?
N1 C2 C9 C14 35.7(6) . . . . ?
C14 C9 C10 C11 -0.4(7) . . . . ?
C2 C9 C10 C11 179.7(4) . . . . ?
C9 C10 C11 C12 -1.9(7) . . . . ?
C10 C11 C12 C13 2.9(7) . . . . ?
C11 C12 C13 C14 -1.4(7) . . . . ?
C10 C9 C14 C13 1.9(7) . . . . ?
C2 C9 C14 C13 -178.3(4) . . . . ?
C12 C13 C14 C9 -0.9(7) . . . . ?
C1 N2 C15 C16 -101.6(5) . . . . ?
N3 N2 C15 C16 73.1(4) . . . . ?
C1 N2 C15 C17 137.8(4) . . . . ?
N3 N2 C15 C17 -47.5(5) . . . . ?
C1 N2 C15 C18 18.3(6) . . . . ?
N3 N2 C15 C18 -167.0(3) . . . . ?

_refine_diff_density_max         1.132
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.098

####################################################################### 
# 
# 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_nk346
_database_code_depnum_ccdc_archive 'CCDC 2069435'
loop_
_audit_author_name
_audit_author_address
'Nikolai Korotkikh'
;The institute of Organic Chemistry, Kyiv
Ukraine
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 F2 N3'
_chemical_formula_weight         313.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   5.4869(3)
_cell_length_b                   10.1446(6)
_cell_length_c                   14.6445(8)
_cell_angle_alpha                101.552(4)
_cell_angle_beta                 93.625(4)
_cell_angle_gamma                93.431(4)
_cell_volume                     794.84(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11995
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.247
_diffrn_reflns_theta_max         25.694
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3020
_reflns_number_gt                1908
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0638P)²] 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         3020
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.9913(2) 0.40193(13) 0.61260(9) 0.0474(4) Uani 1 1 d . . . . .
F2 F 0.3680(3) 0.33086(14) 0.36977(9) 0.0541(5) Uani 1 1 d . . . . .
N1 N 0.7938(3) 0.19401(17) 0.68737(12) 0.0261(4) Uani 1 1 d . . . . .
N2 N 1.0004(3) 0.09085(17) 0.77212(12) 0.0274(5) Uani 1 1 d . . . . .
N3 N 0.9179(3) 0.19848(18) 0.83435(12) 0.0309(5) Uani 1 1 d . . . . .
C1 C 0.9298(4) 0.0816(2) 0.68120(16) 0.0307(6) Uani 1 1 d . . . . .
C2 C 0.7921(4) 0.2615(2) 0.77928(15) 0.0270(5) Uani 1 1 d . . . . .
C3 C 0.6799(4) 0.2299(2) 0.60564(14) 0.0267(5) Uani 1 1 d . . . . .
C4 C 0.7840(4) 0.3329(2) 0.56885(15) 0.0298(5) Uani 1 1 d . . . . .
C5 C 0.6832(4) 0.3684(2) 0.48951(16) 0.0367(6) Uani 1 1 d . . . . .
H5 H 0.757049 0.439246 0.464623 0.044 Uiso 1 1 calc R U . . .
C6 C 0.4717(5) 0.2969(2) 0.44808(15) 0.0350(6) Uani 1 1 d . . . . .
C7 C 0.3584(4) 0.1932(2) 0.48107(16) 0.0366(6) Uani 1 1 d . . . . .
H7 H 0.211625 0.145893 0.450427 0.044 Uiso 1 1 calc R U . . .
C8 C 0.4673(4) 0.1605(2) 0.56102(15) 0.0328(6) Uani 1 1 d . . . . .
H8 H 0.394108 0.089012 0.585435 0.039 Uiso 1 1 calc R U . . .
C9 C 1.1316(4) -0.0118(2) 0.81237(15) 0.0292(5) Uani 1 1 d . . . . .
C10 C 1.2708(5) -0.0931(3) 0.73668(17) 0.0521(8) Uani 1 1 d . . . . .
H10A H 1.357762 -0.160888 0.762238 0.078 Uiso 1 1 calc R U . . .
H10B H 1.155312 -0.138231 0.684413 0.078 Uiso 1 1 calc R U . . .
H10C H 1.389037 -0.032665 0.714563 0.078 Uiso 1 1 calc R U . . .
C11 C 0.9427(4) -0.1022(3) 0.8461(2) 0.0504(7) Uani 1 1 d . . . . .
H11A H 1.024987 -0.170493 0.872807 0.076 Uiso 1 1 calc R U . . .
H11B H 0.852633 -0.047866 0.893882 0.076 Uiso 1 1 calc R U . . .
H11C H 0.828243 -0.146854 0.793340 0.076 Uiso 1 1 calc R U . . .
C12 C 1.3088(4) 0.0611(2) 0.89303(17) 0.0451(7) Uani 1 1 d . . . . .
H12A H 1.396268 -0.005087 0.920130 0.068 Uiso 1 1 calc R U . . .
H12B H 1.426768 0.120859 0.870134 0.068 Uiso 1 1 calc R U . . .
H12C H 1.217687 0.114686 0.940880 0.068 Uiso 1 1 calc R U . . .
C13 C 0.6744(4) 0.3868(2) 0.81483(15) 0.0285(5) Uani 1 1 d . . . . .
C14 C 0.4564(4) 0.4195(2) 0.77365(16) 0.0363(6) Uani 1 1 d . . . . .
H14 H 0.377976 0.360732 0.719699 0.044 Uiso 1 1 calc R U . . .
C15 C 0.3543(5) 0.5382(2) 0.81167(17) 0.0421(7) Uani 1 1 d . . . . .
H15 H 0.206903 0.560947 0.782956 0.051 Uiso 1 1 calc R U . . .
C16 C 0.4642(5) 0.6231(2) 0.89051(17) 0.0421(7) Uani 1 1 d . . . . .
H16 H 0.392285 0.703766 0.916300 0.050 Uiso 1 1 calc R U . . .
C17 C 0.6796(5) 0.5909(2) 0.93219(17) 0.0464(7) Uani 1 1 d . . . . .
H17 H 0.755684 0.648943 0.986907 0.056 Uiso 1 1 calc R U . . .
C18 C 0.7832(4) 0.4741(2) 0.89392(16) 0.0377(6) Uani 1 1 d . . . . .
H18 H 0.932397 0.452996 0.922296 0.045 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 C4 1.352(2) . ?
F2 C6 1.363(2) . ?
N1 C2 1.383(3) . ?
N1 C1 1.390(3) . ?
N1 C3 1.436(2) . ?
N2 C1 1.346(3) . ?
N2 N3 1.393(2) . ?
N2 C9 1.494(3) . ?
N3 C2 1.313(2) . ?
C2 C13 1.476(3) . ?
C3 C4 1.379(3) . ?
C3 C8 1.380(3) . ?
C4 C5 1.377(3) . ?
C5 C6 1.369(3) . ?
C6 C7 1.374(3) . ?
C7 C8 1.389(3) . ?
C9 C11 1.514(3) . ?
C9 C12 1.519(3) . ?
C9 C10 1.519(3) . ?
C13 C18 1.386(3) . ?
C13 C14 1.393(3) . ?
C14 C15 1.387(3) . ?
C15 C16 1.375(3) . ?
C16 C17 1.382(3) . ?
C17 C18 1.376(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 110.84(16) . . ?
C2 N1 C3 127.55(16) . . ?
C1 N1 C3 121.60(17) . . ?
C1 N2 N3 116.10(16) . . ?
C1 N2 C9 125.85(17) . . ?
N3 N2 C9 117.61(16) . . ?
C2 N3 N2 103.09(16) . . ?
N2 C1 N1 100.14(17) . . ?
N3 C2 N1 109.82(17) . . ?
N3 C2 C13 122.59(19) . . ?
N1 C2 C13 127.58(18) . . ?
C4 C3 C8 118.5(2) . . ?
C4 C3 N1 120.6(2) . . ?
C8 C3 N1 120.91(19) . . ?
F1 C4 C5 118.9(2) . . ?
F1 C4 C3 118.80(19) . . ?
C5 C4 C3 122.3(2) . . ?
C6 C5 C4 117.0(2) . . ?
F2 C6 C5 118.0(2) . . ?
F2 C6 C7 118.3(2) . . ?
C5 C6 C7 123.7(2) . . ?
C6 C7 C8 117.3(2) . . ?
C3 C8 C7 121.2(2) . . ?
N2 C9 C11 108.09(17) . . ?
N2 C9 C12 108.60(18) . . ?
C11 C9 C12 110.7(2) . . ?
N2 C9 C10 108.68(17) . . ?
C11 C9 C10 110.6(2) . . ?
C12 C9 C10 110.09(19) . . ?
C18 C13 C14 118.69(19) . . ?
C18 C13 C2 118.39(19) . . ?
C14 C13 C2 122.9(2) . . ?
C15 C14 C13 119.8(2) . . ?
C16 C15 C14 120.6(2) . . ?
C15 C16 C17 119.9(2) . . ?
C18 C17 C16 119.6(2) . . ?
C17 C18 C13 121.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 N3 C2 -1.1(2) . . . . ?
C9 N2 N3 C2 -173.94(18) . . . . ?
N3 N2 C1 N1 0.7(2) . . . . ?
C9 N2 C1 N1 172.84(19) . . . . ?
C2 N1 C1 N2 0.0(2) . . . . ?
C3 N1 C1 N2 178.92(18) . . . . ?
N2 N3 C2 N1 1.0(2) . . . . ?
N2 N3 C2 C13 -178.05(19) . . . . ?
C1 N1 C2 N3 -0.7(3) . . . . ?
C3 N1 C2 N3 -179.5(2) . . . . ?
C1 N1 C2 C13 178.3(2) . . . . ?
C3 N1 C2 C13 -0.5(4) . . . . ?
C2 N1 C3 C4 76.9(3) . . . . ?
C1 N1 C3 C4 -101.9(2) . . . . ?
C2 N1 C3 C8 -104.6(3) . . . . ?
C1 N1 C3 C8 76.7(3) . . . . ?
C8 C3 C4 F1 179.55(18) . . . . ?
N1 C3 C4 F1 -1.9(3) . . . . ?
C8 C3 C4 C5 0.0(3) . . . . ?
N1 C3 C4 C5 178.57(18) . . . . ?
F1 C4 C5 C6 -179.25(19) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 F2 179.61(18) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
F2 C6 C7 C8 -179.94(18) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C4 C3 C8 C7 -0.3(3) . . . . ?
N1 C3 C8 C7 -178.91(18) . . . . ?
C6 C7 C8 C3 0.3(3) . . . . ?
C1 N2 C9 C11 -95.0(3) . . . . ?
N3 N2 C9 C11 77.1(2) . . . . ?
C1 N2 C9 C12 144.8(2) . . . . ?
N3 N2 C9 C12 -43.1(2) . . . . ?
C1 N2 C9 C10 25.1(3) . . . . ?
N3 N2 C9 C10 -162.83(19) . . . . ?
N3 C2 C13 C18 31.0(3) . . . . ?
N1 C2 C13 C18 -147.9(2) . . . . ?
N3 C2 C13 C14 -147.5(2) . . . . ?
N1 C2 C13 C14 33.6(3) . . . . ?
C18 C13 C14 C15 0.5(4) . . . . ?
C2 C13 C14 C15 179.0(2) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C16 C17 C18 C13 -0.8(4) . . . . ?
C14 C13 C18 C17 0.4(4) . . . . ?
C2 C13 C18 C17 -178.2(2) . . . . ?

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_k70
_database_code_depnum_ccdc_archive 'CCDC 2069436'
loop_
_audit_author_name
_audit_author_address
'Nikolai Korotkikh'
;The institute of Organic Chemistry, Kyiv
Ukraine
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H31 Br N3 O6.50 S'
_chemical_formula_weight         541.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   18.9632(7)
_cell_length_b                   18.2169(7)
_cell_length_c                   14.9312(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.5498(11)
_cell_angle_gamma                90
_cell_volume                     4829.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             2248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.832
_shelx_estimated_absorpt_T_min   0.506
_shelx_estimated_absorpt_T_max   0.711
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28950
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.601
_diffrn_reflns_theta_max         26.542
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5022
_reflns_number_gt                3819
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0975P)²+8.3370P] 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         5022
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1591
_refine_ls_wR_factor_gt          0.1391
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          1.791
_refine_ls_shift/su_mean         0.038

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 0.35820(16) 0.79385(17) 0.3325(2) 0.0314(6) Uani 1 1 d . . . . .
N2 N 0.35871(16) 0.79555(18) 0.2407(2) 0.0345(7) Uani 1 1 d . . . . .
C3 C 0.29538(19) 0.82633(19) 0.1895(2) 0.0300(7) Uani 1 1 d . . . . .
N4 N 0.25405(15) 0.84262(15) 0.24666(18) 0.0252(6) Uani 1 1 d . . . . .
C5 C 0.29540(19) 0.82273(18) 0.3371(2) 0.0269(7) Uani 1 1 d . . . . .
C6 C 0.4241(2) 0.7584(2) 0.4087(3) 0.0380(9) Uani 1 1 d . . . . .
C7A C 0.3933(3) 0.6898(3) 0.4450(4) 0.0556(17) Uani 0.775(7) 1 d . . P A 1
H7A1 H 0.434700 0.665239 0.494833 0.083 Uiso 0.775(7) 1 calc R U P A 1
H7A2 H 0.355061 0.705158 0.471407 0.083 Uiso 0.775(7) 1 calc R U P A 1
H7A3 H 0.370776 0.655920 0.391639 0.083 Uiso 0.775(7) 1 calc R U P A 1
C7B C 0.4151(13) 0.7624(15) 0.5056(13) 0.068(8) Uani 0.225(7) 1 d . . P A 2
H7B1 H 0.415947 0.813813 0.525127 0.102 Uiso 0.225(7) 1 calc R U P A 2
H7B2 H 0.367049 0.740033 0.501483 0.102 Uiso 0.225(7) 1 calc R U P A 2
H7B3 H 0.456546 0.735786 0.552916 0.102 Uiso 0.225(7) 1 calc R U P A 2
C8A C 0.4616(3) 0.8120(4) 0.4882(4) 0.0530(17) Uani 0.775(7) 1 d . . P A 1
H8A1 H 0.504228 0.788065 0.536907 0.080 Uiso 0.775(7) 1 calc R U P A 1
H8A2 H 0.479774 0.854457 0.462126 0.080 Uiso 0.775(7) 1 calc R U P A 1
H8A3 H 0.425248 0.828468 0.517048 0.080 Uiso 0.775(7) 1 calc R U P A 1
C8B C 0.4892(9) 0.8040(11) 0.4032(14) 0.051(6) Uani 0.225(7) 1 d . . P A 2
H8B1 H 0.485957 0.853675 0.426495 0.076 Uiso 0.225(7) 1 calc R U P A 2
H8B2 H 0.536850 0.781361 0.442822 0.076 Uiso 0.225(7) 1 calc R U P A 2
H8B3 H 0.486962 0.806321 0.336675 0.076 Uiso 0.225(7) 1 calc R U P A 2
C9A C 0.4812(3) 0.7314(4) 0.3637(4) 0.064(2) Uani 0.775(7) 1 d . . P A 1
H9A1 H 0.524076 0.708316 0.413081 0.096 Uiso 0.775(7) 1 calc R U P A 1
H9A2 H 0.456872 0.695510 0.313434 0.096 Uiso 0.775(7) 1 calc R U P A 1
H9A3 H 0.498904 0.773156 0.336030 0.096 Uiso 0.775(7) 1 calc R U P A 1
C9B C 0.4233(11) 0.6842(9) 0.3762(15) 0.047(5) Uani 0.225(7) 1 d . . P A 2
H9B1 H 0.379838 0.658317 0.381911 0.071 Uiso 0.225(7) 1 calc R U P A 2
H9B2 H 0.419893 0.684344 0.309158 0.071 Uiso 0.225(7) 1 calc R U P A 2
H9B3 H 0.469781 0.659384 0.415305 0.071 Uiso 0.225(7) 1 calc R U P A 2
C10 C 0.2713(2) 0.83728(18) 0.4206(2) 0.0288(7) Uani 1 1 d . . . . .
H10A H 0.299260 0.804323 0.473959 0.035 Uiso 1 1 calc R U . . .
H10B H 0.216981 0.826288 0.402488 0.035 Uiso 1 1 calc R U . . .
C11 C 0.2858(2) 0.91742(19) 0.4541(2) 0.0335(8) Uani 1 1 d . . . . .
H11A H 0.340066 0.928373 0.471381 0.040 Uiso 1 1 calc R U . . .
H11B H 0.257615 0.950201 0.400568 0.040 Uiso 1 1 calc R U . . .
C12 C 0.2623(2) 0.93349(19) 0.5393(2) 0.0313(7) Uani 1 1 d . . . . .
H12A H 0.208649 0.919877 0.522586 0.038 Uiso 1 1 calc R U . B 2
H12B H 0.266452 0.986998 0.551635 0.038 Uiso 1 1 calc R U . B 2
S13 S 0.31589(5) 0.88688(5) 0.64679(6) 0.0326(2) Uani 1 1 d . . . C 2
O14 O 0.39422(16) 0.8997(2) 0.6563(2) 0.0594(9) Uani 1 1 d . . . . .
O15 O 0.29741(15) 0.92235(15) 0.72207(17) 0.0407(6) Uani 1 1 d . . . . .
O16 O 0.2959(2) 0.81043(16) 0.6347(2) 0.0606(9) Uani 1 1 d . . . . .
C17 C 0.2738(2) 0.8414(2) 0.0874(2) 0.0325(8) Uani 1 1 d . . . . .
C18 C 0.2013(2) 0.8321(2) 0.0230(3) 0.0378(8) Uani 1 1 d . . . . .
H18 H 0.162627 0.815943 0.045039 0.045 Uiso 1 1 calc R U . . .
C19 C 0.1848(2) 0.8463(2) -0.0735(3) 0.0449(10) Uani 1 1 d . . . . .
H19 H 0.134676 0.840351 -0.116983 0.054 Uiso 1 1 calc R U . . .
C20 C 0.2401(3) 0.8689(2) -0.1066(3) 0.0464(10) Uani 1 1 d . . . . .
H20 H 0.228641 0.877866 -0.172880 0.056 Uiso 1 1 calc R U . . .
C21 C 0.3123(3) 0.8785(2) -0.0434(3) 0.0480(10) Uani 1 1 d . . . . .
H21 H 0.350536 0.894337 -0.066361 0.058 Uiso 1 1 calc R U . . .
C22 C 0.3300(2) 0.8654(2) 0.0533(3) 0.0411(9) Uani 1 1 d . . . . .
H22 H 0.379999 0.872683 0.096379 0.049 Uiso 1 1 calc R U . . .
C23 C 0.18072(18) 0.87738(18) 0.2164(2) 0.0251(7) Uani 1 1 d . . . . .
C24 C 0.11732(19) 0.83540(18) 0.2073(2) 0.0275(7) Uani 1 1 d . . . . .
H24 H 0.121967 0.784774 0.223597 0.033 Uiso 1 1 calc R U . . .
C25 C 0.04728(19) 0.8688(2) 0.1739(2) 0.0304(7) Uani 1 1 d . . . . .
H25 H 0.003027 0.841412 0.166872 0.036 Uiso 1 1 calc R U . . .
C26 C 0.04272(19) 0.9425(2) 0.1510(2) 0.0312(7) Uani 1 1 d . . . . .
C27 C 0.1057(2) 0.9842(2) 0.1612(3) 0.0336(8) Uani 1 1 d . . . . .
H27 H 0.100970 1.034941 0.145780 0.040 Uiso 1 1 calc R U . . .
C28 C 0.17577(19) 0.95140(19) 0.1942(2) 0.0294(7) Uani 1 1 d . . . . .
H28 H 0.219846 0.979172 0.201430 0.035 Uiso 1 1 calc R U . . .
BR29 Br -0.05329(2) 0.98882(3) 0.10553(3) 0.04704(17) Uani 1 1 d . . . . .
O30 O 0.3903(3) 0.9656(3) 0.3297(4) 0.097(2) Uani 0.968(14) 1 d . . . . .
O31 O 0.500000 0.7844(2) 0.750000 0.0483(10) Uani 1 2 d S T P . .
O32A O 0.500000 1.000000 0.500000 0.034(3) Uiso 0.46(2) 2 d S . P D 1
O32B O 0.5249(14) 0.9979(10) 0.4266(18) 0.329(11) Uiso 0.768(10) 1 d . . P D 2
O33A O 0.4630(4) 0.9126(4) 0.2784(5) 0.0239(15) Uiso 0.3 1 d . . P E 1
O33B O 0.500000 0.9920(6) 0.250000 0.102(4) Uiso 0.6 2 d S . P F 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
N1 C5 1.326(4) . ?
N1 N2 1.374(4) . ?
N1 C6 1.509(4) . ?
N2 C3 1.303(4) . ?
C3 N4 1.378(4) . ?
C3 C17 1.460(5) . ?
N4 C5 1.352(4) . ?
N4 C23 1.448(4) . ?
C5 C10 1.493(4) . ?
C6 C9B 1.434(17) . ?
C6 C8B 1.514(17) . ?
C6 C8A 1.509(7) . ?
C6 C7B 1.517(18) . ?
C6 C9A 1.541(6) . ?
C6 C7A 1.554(7) . ?
C10 C11 1.536(5) . ?
C11 C12 1.517(5) . ?
C12 S13 1.785(3) . ?
S13b O16 1.438(3) . ?
S13b O15 1.442(3) . ?
S13b O14 1.460(3) . ?
C17 C18 1.383(5) . ?
C17 C22 1.403(5) . ?
C18 C19 1.387(5) . ?
C19 C20 1.371(6) . ?
C20 C21 1.374(6) . ?
C21 C22 1.382(5) . ?
C23 C28 1.384(5) . ?
C23 C24 1.391(4) . ?
C24 C25 1.385(5) . ?
C25 C26 1.380(5) . ?
C26 C27 1.378(5) . ?
C26 BR29 1.903(3) . ?
C27 C28 1.380(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 N2 111.3(3) . . ?
C5 N1 C6 130.7(3) . . ?
N2 N1 C6 117.9(3) . . ?
C3 N2 N1 105.5(3) . . ?
N2 C3 N4 109.7(3) . . ?
N2 C3 C17 123.8(3) . . ?
N4 C3 C17 126.5(3) . . ?
C5 N4 C3 107.7(3) . . ?
C5 N4 C23 125.8(3) . . ?
C3 N4 C23 126.4(3) . . ?
N1 C5 N4 105.7(3) . . ?
N1 C5 C10 131.1(3) . . ?
N4 C5 C10 123.1(3) . . ?
C9Bb C6 C8B 114.2(12) . . ?
C9Bb C6 N1 103.9(8) . . ?
C8Bb C6 N1 101.5(7) . . ?
N1 C6 C8A 110.7(3) . . ?
C9Bb C6 C7B 112.1(14) . . ?
C8Bb C6 C7B 113.1(14) . . ?
N1 C6 C7B 111.0(7) . . ?
N1 C6 C9A 109.3(3) . . ?
C8Aa C6 C9A 109.9(4) . . ?
N1 C6 C7A 107.1(3) . . ?
C8Aa C6 C7A 112.2(4) . . ?
C9Aa C6 C7A 107.6(4) . . ?
C5 C10 C11 111.6(3) . . ?
C12 C11 C10 112.7(3) . . ?
C11 C12 S13 114.9(2) . . ?
O16 S13b O15 113.96(18) . . ?
O16 S13b O14 112.4(2) . . ?
O15 S13b O14 111.70(18) . . ?
O16 S13b C12 107.79(18) . . ?
O15 S13b C12 105.68(16) . . ?
O14 S13b C12 104.50(18) . . ?
C18 C17 C22 118.8(3) . . ?
C18 C17 C3 123.3(3) . . ?
C22 C17 C3 117.9(3) . . ?
C17 C18 C19 120.4(4) . . ?
C20 C19 C18 120.5(4) . . ?
C21 C20 C19 119.6(4) . . ?
C20 C21 C22 120.9(4) . . ?
C21 C22 C17 119.7(4) . . ?
C28 C23 C24 121.9(3) . . ?
C28 C23 N4 118.5(3) . . ?
C24 C23 N4 119.5(3) . . ?
C25 C24 C23 118.7(3) . . ?
C26 C25 C24 119.0(3) . . ?
C27 C26 C25 122.1(3) . . ?
C27 C26 BR29 118.6(3) . . ?
C25 C26 BR29 119.3(3) . . ?
C26 C27 C28 119.3(3) . . ?
C27 C28 C23 118.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 C3 0.4(4) . . . . ?
C6 N1 N2 C3 177.9(3) . . . . ?
N1 N2 C3 N4 -1.4(4) . . . . ?
N1 N2 C3 C17 177.9(3) . . . . ?
N2 C3 N4 C5 1.9(4) . . . . ?
C17 C3 N4 C5 -177.3(3) . . . . ?
N2 C3 N4 C23 179.7(3) . . . . ?
C17 C3 N4 C23 0.5(5) . . . . ?
N2 N1 C5 N4 0.8(4) . . . . ?
C6 N1 C5 N4 -176.4(3) . . . . ?
N2 N1 C5 C10 -175.7(3) . . . . ?
C6 N1 C5 C10 7.2(6) . . . . ?
C3 N4 C5 N1 -1.6(4) . . . . ?
C23 N4 C5 N1 -179.4(3) . . . . ?
C3 N4 C5 C10 175.2(3) . . . . ?
C23 N4 C5 C10 -2.6(5) . . . . ?
C5 N1 C6 C9Bb 116.8(9) . . . . ?
N2 N1 C6 C9Bb -60.2(9) . . . . ?
C5 N1 C6 C8Bb -124.4(10) . . . . ?
N2 N1 C6 C8Bb 58.6(10) . . . . ?
C5 N1 C6 C8Aa -61.0(5) . . . . ?
N2 N1 C6 C8Aa 122.0(4) . . . . ?
C5 N1 C6 C7Bb -3.9(13) . . . . ?
N2 N1 C6 C7Bb 179.1(13) . . . . ?
C5 N1 C6 C9Aa 177.9(5) . . . . ?
N2 N1 C6 C9Aa 0.8(5) . . . . ?
C5 N1 C6 C7Aa 61.6(5) . . . . ?
N2 N1 C6 C7Aa -115.5(4) . . . . ?
N1 C5 C10 C11 97.5(4) . . . . ?
N4 C5 C10 C11 -78.4(4) . . . . ?
C5 C10 C11 C12 -179.6(3) . . . . ?
C10 C11 C12 S13b 66.0(4) . . . . ?
C11 C12 S13b O16 -71.2(3) . . . . ?
C11 C12 S13b O15 166.6(3) . . . . ?
C11 C12 S13b O14 48.6(3) . . . . ?
N2 C3 C17 C18 140.5(4) . . . . ?
N4 C3 C17 C18 -40.4(6) . . . . ?
N2 C3 C17 C22 -38.5(5) . . . . ?
N4 C3 C17 C22 140.6(4) . . . . ?
C22 C17 C18 C19 0.1(6) . . . . ?
C3 C17 C18 C19 -179.0(4) . . . . ?
C17 C18 C19 C20 0.8(6) . . . . ?
C18 C19 C20 C21 -0.9(6) . . . . ?
C19 C20 C21 C22 0.3(7) . . . . ?
C20 C21 C22 C17 0.6(7) . . . . ?
C18 C17 C22 C21 -0.7(6) . . . . ?
C3 C17 C22 C21 178.4(4) . . . . ?
C5 N4 C23 C28 105.3(4) . . . . ?
C3 N4 C23 C28 -72.1(4) . . . . ?
C5 N4 C23 C24 -77.0(4) . . . . ?
C3 N4 C23 C24 105.6(4) . . . . ?
C28 C23 C24 C25 0.7(5) . . . . ?
N4 C23 C24 C25 -176.9(3) . . . . ?
C23 C24 C25 C26 -0.1(5) . . . . ?
C24 C25 C26 C27 -0.7(5) . . . . ?
C24 C25 C26 BR29 -179.8(2) . . . . ?
C25 C26 C27 C28 0.9(5) . . . . ?
BR29 C26 C27 C28 180.0(2) . . . . ?
C26 C27 C28 C23 -0.3(5) . . . . ?
C24 C23 C28 C27 -0.5(5) . . . . ?
N4 C23 C28 C27 177.1(3) . . . . ?

_refine_diff_density_max         1.323
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.100

