# Electronic Supplementary Material (ESI) for ChemComm.
# 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_mj21023_0m_pl
_database_code_depnum_ccdc_archive 'CCDC 2063796'
loop_
_audit_author_name
_audit_author_address
'Jie Li'
;Chengdu University of Information Technology
China
;
_audit_update_record             
;
2021-02-19 deposited with the CCDC.	2021-05-21 downloaded from the CCDC.
;
_audit_creation_date             2021-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(C39 H29 Br1 N6)'
_chemical_formula_sum            'C39 H29 Br N6'
_chemical_formula_weight         661.58
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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'
Br Br -0.9502 1.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c'
_space_group_name_Hall           '-R 3 2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'-x, -x+y, -z+1/2'
'x-y, -y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'x, x-y, z-1/2'
'-x+y, y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'

_cell_length_a                   14.6985(7)
_cell_length_b                   14.6985(7)
_cell_length_c                   26.0926(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4882.0(5)
_cell_formula_units_Z            6.00012
_cell_measurement_reflns_used    4317
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      48.50
_cell_measurement_theta_min      3.37
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.367
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1416 before and 0.0917 after correction. The Ratio of minimum to maximum transmission is 0.7364. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2040
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1512
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10556
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.921
_diffrn_reflns_theta_min         5.236
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                686
_reflns_number_total             984
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     79
_refine_ls_number_reflns         984
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.1029
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1812P)²+4.2124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2892
_refine_ls_wR_factor_ref         0.3186
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: Br1(0.1667) H5(0.8333)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.2642(4) 0.5461(5) 0.0948(3) 0.180(2) Uani 0.1667 1 d . . . A 2
N1 N -0.2398(3) 0.333333 0.083333 0.0793(13) Uani 1 2 d S T P . .
N2 N -0.1519(3) 0.5147(3) 0.083333 0.0812(13) Uani 1 2 d S T P . .
C1 C -0.2454(3) 0.4213(3) 0.083333 0.0758(13) Uani 1 2 d S T P . .
C2 C -0.0530(3) 0.5177(3) 0.08966(16) 0.0802(12) Uani 1 1 d . . . . .
C3 C -0.0333(3) 0.4749(4) 0.1329(2) 0.1037(15) Uani 1 1 d . . . . .
H3 H -0.085020 0.442692 0.157873 0.124 Uiso 1 1 calc R . . . .
C4 C 0.0615(4) 0.4799(4) 0.1390(3) 0.1161(18) Uani 1 1 d . . . . .
H4 H 0.074475 0.452055 0.168289 0.139 Uiso 1 1 calc R . . . .
C5 C 0.1372(5) 0.5258(5) 0.1023(3) 0.129(2) Uani 1 1 d . . . . .
H5 H 0.199377 0.523952 0.104887 0.155 Uiso 0.8333 1 calc R . . A 1
C6 C 0.1206(4) 0.5748(6) 0.0612(3) 0.132(2) Uani 1 1 d . . . . .
H6 H 0.174685 0.612548 0.037968 0.158 Uiso 1 1 calc R . . . .
C7 C 0.0249(4) 0.5684(5) 0.0542(2) 0.1099(16) Uani 1 1 d . . . . .
H7 H 0.013109 0.598409 0.025477 0.132 Uiso 1 1 calc R . . . .


_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 Br1 2.668(11) 2_665 ?
Br1 Br1 2.668(11) 3_565 ?
Br1 C5 1.747(7) . ?
N1 C1 1.336(3) . ?
N1 C1 1.336(3) 3_455 ?
N2 C1 1.374(6) . ?
N2 C2 1.442(4) . ?
N2 C2 1.442(4) 16_454 ?
C2 C3 1.391(6) . ?
C2 C7 1.366(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.364(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(10) . ?
C6 H6 0.9300 . ?
C6 C7 1.374(7) . ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br1 Br1 Br1 60.000(1) 3_565 2_665 ?
C5 Br1 Br1 73.5(4) . 3_565 ?
C5 Br1 Br1 133.1(4) . 2_665 ?
C1 N1 C1 113.9(5) 3_455 . ?
C1 N2 C2 121.3(2) . 16_454 ?
C1 N2 C2 121.3(2) . . ?
C2 N2 C2 117.4(4) 16_454 . ?
N1 C1 N1 126.1(5) 2_565 . ?
N1 C1 N2 116.9(2) 2_565 . ?
N1 C1 N2 116.9(2) . . ?
C3 C2 N2 120.9(3) . . ?
C7 C2 N2 119.8(4) . . ?
C7 C2 C3 119.2(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.1(5) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 Br1 134.4(6) . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(5) . . ?
C6 C5 Br1 106.1(5) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.5(5) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 119.9(5) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?

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
Br1 Br1 C5 C4 -120.1(8) 3_565 . . . ?
Br1 Br1 C5 C4 -112.2(7) 2_665 . . . ?
Br1 Br1 C5 C6 63.8(6) 2_665 . . . ?
Br1 Br1 C5 C6 55.9(4) 3_565 . . . ?
Br1 C5 C6 C7 176.5(6) . . . . ?
N2 C2 C3 C4 -178.8(4) . . . . ?
N2 C2 C7 C6 177.5(5) . . . . ?
C1 N1 C1 N1 0.0 3_455 . . 2_565 ?
C1 N1 C1 N2 180.0 3_455 . . . ?
C1 N2 C2 C3 -58.0(4) . . . . ?
C1 N2 C2 C7 125.8(4) . . . . ?
C2 N2 C1 N1 172.30(19) . . . 2_565 ?
C2 N2 C1 N1 172.29(19) 16_454 . . . ?
C2 N2 C1 N1 -7.71(19) 16_454 . . 2_565 ?
C2 N2 C1 N1 -7.70(19) . . . . ?
C2 N2 C2 C3 122.0(4) 16_454 . . . ?
C2 N2 C2 C7 -54.2(4) 16_454 . . . ?
C2 C3 C4 C5 -0.9(8) . . . . ?
C3 C2 C7 C6 1.2(8) . . . . ?
C3 C4 C5 Br1 -178.9(6) . . . . ?
C3 C4 C5 C6 5.5(9) . . . . ?
C4 C5 C6 C7 -6.8(10) . . . . ?
C5 C6 C7 C2 3.5(10) . . . . ?
C7 C2 C3 C4 -2.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_YJS-GQ-189
_database_code_depnum_ccdc_archive 'CCDC 2063802'
loop_
_audit_author_name
_audit_author_address
'Jie Li'
;Chengdu University of Information Technology
China
;
_audit_update_record             
;
2021-02-19 deposited with the CCDC.	2021-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H29 Cl N6'
_chemical_formula_weight         617.13

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'
Cl Cl 0.3639 0.7018 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c :H'
_space_group_name_Hall           '-R 3 2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   14.6313(7)
_cell_length_b                   14.6313(7)
_cell_length_c                   25.8672(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4795.6(5)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6238
_cell_measurement_theta_min      3.878
_cell_measurement_theta_max      71.13

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             1932
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.352
_shelx_estimated_absorpt_T_min   0.755
_shelx_estimated_absorpt_T_max   0.793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13979
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.1035
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         4.886
_diffrn_reflns_theta_max         71.316
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1040
_reflns_number_gt                908
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.1938P)²+12.5485P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1040
_refine_ls_number_parameters     83
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.1087
_refine_ls_wR_factor_ref         0.3165
_refine_ls_wR_factor_gt          0.3105
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.041
_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
Cl1 Cl 0.5374(11) 0.2872(10) 0.3931(5) 0.189(7) Uani 0.1667 1 d D . P A 1
N001 N 0.5156(2) 0.6667 0.4167 0.0530(11) Uani 1 2 d S T P . .
N002 N 0.3333 0.5725(2) 0.4167 0.0521(11) Uani 1 2 d S T P . .
C003 C 0.4219(3) 0.6667 0.4167 0.0462(11) Uani 1 2 d S T P . .
C004 C 0.5180(2) 0.5704(2) 0.41026(13) 0.0528(9) Uani 1 1 d . . . . .
C005 C 0.4760(3) 0.5087(3) 0.36645(18) 0.0706(12) Uani 1 1 d . . . . .
H005 H 0.4451 0.5292 0.3409 0.074(12) Uiso 1 1 calc R . . . .
C006 C 0.5687(4) 0.5429(3) 0.44569(17) 0.0751(12) Uani 1 1 d . . . . .
H006 H 0.5996 0.5858 0.4744 0.109(17) Uiso 1 1 calc R . . . .
C007 C 0.4800(3) 0.4166(3) 0.3608(2) 0.0810(14) Uani 1 1 d D . . . .
H007 H 0.4497 0.3739 0.3320 0.080(13) Uiso 1 1 calc R . . . .
C008 C 0.5751(5) 0.4525(4) 0.4398(2) 0.0963(16) Uani 1 1 d D . . . .
H008 H 0.6106 0.4351 0.4642 0.081(13) Uiso 1 1 calc R . . . .
C009 C 0.5288(4) 0.3884(4) 0.3978(2) 0.0946(17) Uani 1 1 d . . . . .
H009 H 0.5304 0.3260 0.3944 0.114 Uiso 0.8333 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
Cl1 C009 1.553(10) . ?
N001 C003 1.370(5) . ?
N001 C004 1.437(3) . ?
N001 C004 1.437(3) 11_565 ?
N002 C003 1.339(2) . ?
N002 C003 1.339(2) 3_565 ?
C003 N002 1.339(2) 2_665 ?
C004 C006 1.361(5) . ?
C004 C005 1.386(5) . ?
C005 C007 1.386(5) . ?
C005 H005 0.9300 . ?
C006 C008 1.380(6) . ?
C006 H006 0.9300 . ?
C007 C009 1.376(7) . ?
C007 H007 0.9300 . ?
C008 C009 1.373(8) . ?
C008 H008 0.9300 . ?
C009 H009 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C003 N001 C004 121.00(16) . . ?
C003 N001 C004 121.00(16) . 11_565 ?
C004 N001 C004 118.0(3) . 11_565 ?
C003 N002 C003 113.9(4) . 3_565 ?
N002 C003 N002 126.1(4) . 2_665 ?
N002 C003 N001 116.96(19) . . ?
N002 C003 N001 116.96(19) 2_665 . ?
C006 C004 C005 119.3(3) . . ?
C006 C004 N001 119.8(3) . . ?
C005 C004 N001 120.8(3) . . ?
C007 C005 C004 119.9(4) . . ?
C007 C005 H005 120.0 . . ?
C004 C005 H005 120.0 . . ?
C008 C006 C004 121.2(4) . . ?
C008 C006 H006 119.4 . . ?
C004 C006 H006 119.4 . . ?
C005 C007 C009 119.9(4) . . ?
C005 C007 H007 120.0 . . ?
C009 C007 H007 120.0 . . ?
C006 C008 C009 119.7(4) . . ?
C006 C008 H008 120.2 . . ?
C009 C008 H008 120.2 . . ?
C008 C009 C007 120.0(4) . . ?
C008 C009 Cl1 117.7(6) . . ?
C007 C009 Cl1 122.3(6) . . ?
C008 C009 H009 120.0 . . ?
C007 C009 H009 120.0 . . ?

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
C003 N002 C003 N002 0.0 3_565 . . 2_665 ?
C003 N002 C003 N001 180.0 3_565 . . . ?
C004 N001 C003 N002 7.74(16) . . . . ?
C004 N001 C003 N002 -172.25(16) 11_565 . . . ?
C004 N001 C003 N002 -172.26(16) . . . 2_665 ?
C004 N001 C003 N002 7.75(16) 11_565 . . 2_665 ?
C003 N001 C004 C006 -126.0(3) . . . . ?
C004 N001 C004 C006 54.0(3) 11_565 . . . ?
C003 N001 C004 C005 58.7(3) . . . . ?
C004 N001 C004 C005 -121.3(3) 11_565 . . . ?
C006 C004 C005 C007 4.1(6) . . . . ?
N001 C004 C005 C007 179.4(3) . . . . ?
C005 C004 C006 C008 -2.8(6) . . . . ?
N001 C004 C006 C008 -178.1(4) . . . . ?
C004 C005 C007 C009 -2.2(7) . . . . ?
C004 C006 C008 C009 -0.6(8) . . . . ?
C006 C008 C009 C007 2.6(8) . . . . ?
C006 C008 C009 Cl1 -179.6(8) . . . . ?
C005 C007 C009 C008 -1.2(8) . . . . ?
C005 C007 C009 Cl1 -178.9(8) . . . . ?

_refine_diff_density_max         0.494
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_yjs-gq-183
_database_code_depnum_ccdc_archive 'CCDC 2063809'
loop_
_audit_author_name
_audit_author_address
'Jie Li'
;Chengdu University of Information Technology
China
;
_audit_update_record             
;
2021-02-19 deposited with the CCDC.	2021-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H29 F N6'
_chemical_formula_weight         600.68

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      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c :H'
_space_group_name_Hall           '-R 3 2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   14.5389(9)
_cell_length_b                   14.5389(9)
_cell_length_c                   25.5523(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4677.6(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2518
_cell_measurement_theta_min      3.895
_cell_measurement_theta_max      71.698

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             1884
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.649
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5217
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         4.931
_diffrn_reflns_theta_max         71.660
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1011
_reflns_number_gt                937
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0738P)²+2.5495P] 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         1011
_refine_ls_number_parameters     79
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1334
_refine_ls_wR_factor_gt          0.1297
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.121
_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
C1 C 0.6667 0.42216(11) 0.5833 0.0382(4) Uani 1 2 d S T P . .
C2 C 0.76297(10) 0.61635(10) 0.57626(5) 0.0412(4) Uani 1 1 d . . . . .
C3 C 0.82498(12) 0.63541(11) 0.53203(6) 0.0525(4) Uani 1 1 d . . . . .
H3 H 0.8048 0.5831 0.5065 0.063 Uiso 1 1 calc R U . . .
C4 C 0.91685(12) 0.73215(13) 0.52580(8) 0.0615(5) Uani 1 1 d . . . . .
H4 H 0.9589 0.7447 0.4963 0.074 Uiso 1 1 calc R U . . .
C5 C 0.94606(13) 0.80970(13) 0.56316(9) 0.0666(5) Uani 1 1 d D . . . .
H5 H 1.0084 0.8744 0.5591 0.080 Uiso 0.8333 1 calc R U P A 1
F1 F 1.0265(5) 0.9002(5) 0.5651(4) 0.111(3) Uani 0.1667 1 d D . P B 2
C6 C 0.88340(14) 0.79204(12) 0.60650(7) 0.0644(5) Uani 1 1 d . . . . .
H6 H 0.9027 0.8453 0.6314 0.077 Uiso 1 1 calc R U . . .
C7 C 0.79155(12) 0.69504(12) 0.61323(6) 0.0510(4) Uani 1 1 d . . . . .
H7 H 0.7493 0.6831 0.6426 0.061 Uiso 1 1 calc R U . . .
N1 N 0.57197(9) 0.3333 0.5833 0.0421(4) Uani 1 2 d S T P . .
N2 N 0.6667 0.51685(10) 0.5833 0.0434(4) Uani 1 2 d S T P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3361(10) . ?
C1 N1 1.3361(10) 3_665 ?
C1 N2 1.377(2) . ?
C2 C7 1.378(2) . ?
C2 C3 1.385(2) . ?
C2 N2 1.4353(14) . ?
C3 C4 1.382(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 F1 1.250(6) . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
N1 C1 1.3361(10) 2_655 ?
N2 C2 1.4353(14) 18_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N1 126.34(16) . 3_665 ?
N1 C1 N2 116.83(8) . . ?
N1 C1 N2 116.83(8) 3_665 . ?
C7 C2 C3 119.84(13) . . ?
C7 C2 N2 119.20(12) . . ?
C3 C2 N2 120.92(11) . . ?
C4 C3 C2 119.95(14) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.04(16) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
F1 C5 C4 129.4(5) . . ?
F1 C5 C6 110.4(5) . . ?
C4 C5 C6 120.20(15) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 120.13(16) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 119.82(15) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C1 N1 C1 113.66(16) . 2_655 ?
C1 N2 C2 121.34(7) . 18_655 ?
C1 N2 C2 121.34(7) . . ?
C2 N2 C2 117.32(13) 18_655 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 C4 1.8(2) . . . . ?
N2 C2 C3 C4 179.38(13) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C3 C4 C5 F1 178.1(7) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
F1 C5 C6 C7 -177.9(6) . . . . ?
C4 C5 C6 C7 1.3(3) . . . . ?
C3 C2 C7 C6 -1.4(2) . . . . ?
N2 C2 C7 C6 -178.99(13) . . . . ?
C5 C6 C7 C2 -0.2(2) . . . . ?
N1 C1 N1 C1 0.000(0) 3_665 . . 2_655 ?
N2 C1 N1 C1 180.003(1) . . . 2_655 ?
N1 C1 N2 C2 8.47(6) . . . 18_655 ?
N1 C1 N2 C2 -171.53(6) 3_665 . . 18_655 ?
N1 C1 N2 C2 -171.53(6) . . . . ?
N1 C1 N2 C2 8.48(6) 3_665 . . . ?
C7 C2 N2 C1 -124.83(10) . . . . ?
C3 C2 N2 C1 57.59(14) . . . . ?
C7 C2 N2 C2 55.17(10) . . . 18_655 ?
C3 C2 N2 C2 -122.41(14) . . . 18_655 ?

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_yjs-gq-1
_database_code_depnum_ccdc_archive 'CCDC 2063811'
loop_
_audit_author_name
_audit_author_address
'Jie Li'
;Chengdu University of Information Technology
China
;
_audit_update_record             
;
2021-02-19 deposited with the CCDC.	2021-05-21 downloaded from the CCDC.
;
_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38.999 H29.999 N6'
_chemical_formula_sum            'C39 H30 N6'
_chemical_formula_weight         582.68
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c'
_space_group_name_Hall           '-R 3 2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   14.4042(7)
_cell_length_b                   14.4042(7)
_cell_length_c                   25.6105(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4601.8(5)
_cell_formula_units_Z            6.00012
_cell_measurement_reflns_used    2683
_cell_measurement_temperature    295.46(16)
_cell_measurement_theta_max      71.9500
_cell_measurement_theta_min      3.9770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1836
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            4665
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        62.463
_diffrn_reflns_theta_max         62.463
_diffrn_reflns_theta_min         4.949
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.46(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -99.0000  -90.0000 74

#__ type_ start__ end____ width___ exp.time_
  3 omega    7.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   19.0000  -60.0000 100

#__ type_ start__ end____ width___ exp.time_
  4 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
  5 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

#__ type_ start__ end____ width___ exp.time_
  8 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 95

#__ type_ start__ end____ width___ exp.time_
 10 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  120.0000 66

#__ type_ start__ end____ width___ exp.time_
 11 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000    0.0000 95

#__ type_ start__ end____ width___ exp.time_
 12 omega   87.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0779885000
_diffrn_orient_matrix_UB_12      -0.0278014000
_diffrn_orient_matrix_UB_13      -0.0462362000
_diffrn_orient_matrix_UB_21      -0.0890000000
_diffrn_orient_matrix_UB_22      -0.0135956000
_diffrn_orient_matrix_UB_23      0.0380087000
_diffrn_orient_matrix_UB_31      0.0356105000
_diffrn_orient_matrix_UB_32      0.1194257000
_diffrn_orient_matrix_UB_33      -0.0064335000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                765
_reflns_number_total             824
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0129(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         824
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0589
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1330P)²+1.9593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1680
_refine_ls_wR_factor_ref         0.1708
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N001 N 0.48151(12) 0.333333 0.583333 0.0361(7) Uani 1 2 d S T P . .
N002 N 0.666667 0.42893(12) 0.583333 0.0354(7) Uani 1 2 d S T P . .
C003 C 0.57702(14) 0.333333 0.583333 0.0311(7) Uani 1 2 d S T P . .
C004 C 0.38123(13) 0.23608(12) 0.57602(7) 0.0343(7) Uani 1 1 d . . . . .
C005 C 0.30141(14) 0.20607(14) 0.61322(7) 0.0417(7) Uani 1 1 d . . . . .
C006 C 0.36203(14) 0.17359(15) 0.53202(8) 0.0435(7) Uani 1 1 d . . . . .
C007 C 0.26494(16) 0.08084(15) 0.52574(9) 0.0519(7) Uani 1 1 d . . . . .
C008 C 0.20393(15) 0.11337(17) 0.60658(9) 0.0531(7) Uani 1 1 d . . . . .
C009 C 0.18553(16) 0.04953(16) 0.56305(9) 0.0545(7) Uani 1 1 d . . . . .
H005 H 0.3166(18) 0.2536(18) 0.6440(9) 0.051(5) Uiso 1 1 d . . . . .
H008 H 0.146(2) 0.089(2) 0.6356(10) 0.065(7) Uiso 1 1 d . . . . .
H007 H 0.2509(19) 0.033(2) 0.4974(10) 0.060(7) Uiso 1 1 d . . . . .
H006 H 0.417(2) 0.1971(19) 0.5067(8) 0.052(6) Uiso 1 1 d . . . . .
H009 H 0.120(2) -0.015(2) 0.5573(9) 0.058(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N001 C003 1.376(3) . ?
N001 C004 1.4353(18) 17 ?
N001 C004 1.4354(18) . ?
N002 C003 1.3362(14) . ?
N002 C003 1.3362(13) 3_665 ?
C004 C005 1.385(2) . ?
C004 C006 1.381(3) . ?
C005 C008 1.381(3) . ?
C005 H005 0.99(2) . ?
C006 C007 1.378(3) . ?
C006 H006 0.95(2) . ?
C007 C009 1.382(3) . ?
C007 H007 0.95(3) . ?
C008 C009 1.384(3) . ?
C008 H008 1.04(3) . ?
C009 H009 0.94(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
C003 N001 C004 121.22(8) . . ?
C003 N001 C004 121.22(8) . 17 ?
C004 N001 C004 117.56(16) . 17 ?
C003 N002 C003 113.6(2) 3_665 . ?
N002 C003 N001 116.82(10) . . ?
N002 C003 N001 116.82(10) 2_655 . ?
N002 C003 N002 126.4(2) 2_655 . ?
C005 C004 N001 119.20(14) . . ?
C006 C004 N001 121.22(15) . . ?
C006 C004 C005 119.55(16) . . ?
C004 C005 H005 117.9(13) . . ?
C008 C005 C004 120.05(18) . . ?
C008 C005 H005 122.1(13) . . ?
C004 C006 H006 117.8(14) . . ?
C007 C006 C004 120.17(18) . . ?
C007 C006 H006 122.1(14) . . ?
C006 C007 C009 120.60(19) . . ?
C006 C007 H007 122.4(15) . . ?
C009 C007 H007 116.8(15) . . ?
C005 C008 C009 120.39(19) . . ?
C005 C008 H008 119.6(13) . . ?
C009 C008 H008 119.9(13) . . ?
C007 C009 C008 119.21(18) . . ?
C007 C009 H009 117.8(14) . . ?
C008 C009 H009 122.9(14) . . ?

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
N001 C004 C005 C008 179.27(16) . . . . ?
N001 C004 C006 C007 -179.67(15) . . . . ?
C003 N001 C004 C005 124.33(12) . . . . ?
C003 N001 C004 C006 -57.38(17) . . . . ?
C003 N002 C003 N001 180.0 3_665 . . . ?
C003 N002 C003 N002 0.0 3_665 . . 2_655 ?
C004 N001 C003 N002 171.23(8) 17 . . 2_655 ?
C004 N001 C003 N002 171.23(8) . . . . ?
C004 N001 C003 N002 -8.77(8) . . . 2_655 ?
C004 N001 C003 N002 -8.77(8) 17 . . . ?
C004 N001 C004 C005 -55.67(12) 17 . . . ?
C004 N001 C004 C006 122.62(17) 17 . . . ?
C004 C005 C008 C009 0.5(3) . . . . ?
C004 C006 C007 C009 0.4(3) . . . . ?
C005 C004 C006 C007 -1.4(3) . . . . ?
C005 C008 C009 C007 -1.4(3) . . . . ?
C006 C004 C005 C008 0.9(3) . . . . ?
C006 C007 C009 C008 1.0(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.492 0.750 10.9 2.1 ?
2 0.000 0.508 0.250 10.9 2.1 ?
3 0.158 0.333 0.083 10.9 2.1 ?
4 0.158 0.825 0.583 10.9 2.1 ?
5 0.175 0.333 0.583 10.9 2.1 ?
6 0.175 0.842 0.083 10.9 2.1 ?
7 0.333 0.158 0.417 10.9 2.1 ?
8 0.333 0.175 0.917 10.9 2.1 ?
9 0.492 0.492 0.250 10.9 2.1 ?
10 0.492 1.000 0.750 10.9 2.1 ?
11 0.508 0.508 0.750 10.9 2.1 ?
12 0.508 0.000 0.250 10.9 2.1 ?
13 0.667 0.825 0.083 10.9 2.1 ?
14 0.667 0.842 0.583 10.9 2.1 ?
15 0.825 0.158 0.917 10.9 2.1 ?
16 0.825 0.667 0.417 10.9 2.1 ?
17 0.842 0.175 0.417 10.9 2.1 ?
18 0.842 0.667 0.917 10.9 2.1 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
