# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_o2_sqd
_database_code_depnum_ccdc_archive 'CCDC 1942676'
loop_
_audit_author_name
_audit_author_address
'Zhiyong Guo'
;Fuzhou University
China
;
_audit_update_record             
;
2019-07-23 deposited with the CCDC.	2020-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C50 H28 N6'
_chemical_formula_sum            'C50 H28 N6'
_chemical_formula_weight         712.78

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'

_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                   10.7183(12)
_cell_length_b                   13.8384(16)
_cell_length_c                   14.7191(17)
_cell_angle_alpha                95.994(2)
_cell_angle_beta                 98.595(2)
_cell_angle_gamma                99.932(2)
_cell_volume                     2107.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9948
_cell_measurement_theta_min      1.412
_cell_measurement_theta_max      27.828

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_F_000             740
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.996
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15233
_diffrn_reflns_av_unetI/netI     0.1060
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.412
_diffrn_reflns_theta_max         27.828
_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             9948
_reflns_number_gt                5219
_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 (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)+(0.1657P)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         9948
_refine_ls_number_parameters     505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1473
_refine_ls_R_factor_gt           0.0884
_refine_ls_wR_factor_ref         0.2818
_refine_ls_wR_factor_gt          0.2545
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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
N1 N 1.1538(4) 0.7320(3) 0.7795(3) 0.0511(10) Uani 1 1 d . . . . .
N2 N 1.0465(3) 0.8922(3) 1.0051(2) 0.0363(8) Uani 1 1 d . . . . .
N3 N 0.5509(3) 1.2857(3) 0.6147(2) 0.0414(8) Uani 1 1 d . . . . .
N4 N 0.6500(4) 1.0132(3) 0.5545(2) 0.0641(13) Uani 1 1 d . . . . .
N5 N 0.4929(3) 1.3896(2) 1.05438(18) 0.0253(6) Uani 1 1 d . . . . .
N6 N 0.8861(3) 0.8256(2) 0.38152(18) 0.0257(6) Uani 1 1 d . . . . .
C1 C 0.6017(3) 0.9864(3) 0.8770(2) 0.0272(8) Uani 1 1 d . . . . .
H1 H 0.5369 1.0127 0.9004 0.830 Uiso 1 1 calc R U . . .
C2 C 0.6355(3) 0.9023(3) 0.9073(3) 0.0331(8) Uani 1 1 d . . . . .
H2 H 0.5932 0.8721 0.9507 0.830 Uiso 1 1 calc R U . . .
C3 C 0.7327(3) 0.8620(3) 0.8733(2) 0.0292(8) Uani 1 1 d . . . . .
H3 H 0.7553 0.8050 0.8937 0.830 Uiso 1 1 calc R U . . .
C5 C 0.7613(3) 0.9925(2) 0.7770(2) 0.0239(7) Uani 1 1 d . . . . .
H5 H 0.8028 1.0224 0.7330 0.830 Uiso 1 1 calc R U . . .
C4 C 0.7962(3) 0.9081(3) 0.8081(2) 0.0238(7) Uani 1 1 d . . . . .
C6 C 0.6637(3) 1.0330(2) 0.8115(2) 0.0233(7) Uani 1 1 d . . . . .
C7 C 0.8976(3) 0.8647(2) 0.7702(2) 0.0236(7) Uani 1 1 d . . . . .
C8 C 0.9932(3) 0.8377(3) 0.8283(2) 0.0258(7) Uani 1 1 d . . . . .
C9 C 1.0807(4) 0.7789(3) 0.7980(2) 0.0326(8) Uani 1 1 d . . . . .
C10 C 1.0171(3) 0.8682(3) 0.9269(2) 0.0285(8) Uani 1 1 d . . . . .
C11 C 0.5882(3) 1.1938(2) 0.8479(2) 0.0217(7) Uani 1 1 d . . . . .
C12 C 0.6579(3) 1.2102(2) 0.9392(2) 0.0234(7) Uani 1 1 d . . . . .
H12 H 0.7249 1.1769 0.9542 0.830 Uiso 1 1 calc R U . . .
C13 C 0.6269(3) 1.2755(3) 1.0066(2) 0.0257(7) Uani 1 1 d . . . . .
H13 H 0.6739 1.2864 1.0664 0.830 Uiso 1 1 calc R U . . .
C14 C 0.5249(3) 1.3251(2) 0.9847(2) 0.0238(7) Uani 1 1 d . . . . .
C15 C 0.4548(3) 1.3088(2) 0.8946(2) 0.0237(7) Uani 1 1 d . . . . .
H15 H 0.3871 1.3415 0.8797 0.830 Uiso 1 1 calc R U . . .
C16 C 0.4867(3) 1.2435(2) 0.8273(2) 0.0223(7) Uani 1 1 d . . . . .
H16 H 0.4396 1.2328 0.7676 0.830 Uiso 1 1 calc R U . . .
C17 C 0.3682(3) 1.3947(2) 1.0726(2) 0.0267(7) Uani 1 1 d . . . . .
C18 C 0.2485(4) 1.3544(3) 1.0191(3) 0.0315(8) Uani 1 1 d . . . . .
H18 H 0.2409 1.3170 0.9616 0.830 Uiso 1 1 calc R U . . .
C19 C 0.1398(4) 1.3725(3) 1.0554(3) 0.0378(9) Uani 1 1 d . . . . .
H19 H 0.0586 1.3465 1.0210 0.830 Uiso 1 1 calc R U . . .
C20 C 0.1498(4) 1.4288(3) 1.1422(3) 0.0412(10) Uani 1 1 d . . . . .
H20 H 0.0759 1.4401 1.1642 0.830 Uiso 1 1 calc R U . . .
C21 C 0.2701(4) 1.4675(3) 1.1950(3) 0.0394(9) Uani 1 1 d . . . . .
H21 H 0.2777 1.5039 1.2530 0.830 Uiso 1 1 calc R U . . .
C22 C 0.3798(4) 1.4508(3) 1.1596(2) 0.0299(8) Uani 1 1 d . . . . .
C23 C 0.5148(4) 1.4832(3) 1.1956(2) 0.0287(8) Uani 1 1 d . . . . .
C24 C 0.5824(4) 1.5434(3) 1.2762(3) 0.0362(9) Uani 1 1 d . . . . .
H24 H 0.5394 1.5665 1.3218 0.830 Uiso 1 1 calc R U . . .
C25 C 0.7158(4) 1.5679(3) 1.2864(3) 0.0413(10) Uani 1 1 d . . . . .
H25 H 0.7621 1.6076 1.3398 0.830 Uiso 1 1 calc R U . . .
C26 C 0.7814(4) 1.5342(3) 1.2183(3) 0.0392(9) Uani 1 1 d . . . . .
H26 H 0.8703 1.5530 1.2262 0.830 Uiso 1 1 calc R U . . .
C27 C 0.7149(4) 1.4723(3) 1.1380(2) 0.0337(9) Uani 1 1 d . . . . .
H27 H 0.7581 1.4497 1.0923 0.830 Uiso 1 1 calc R U . . .
C28 C 0.5819(3) 1.4459(2) 1.1293(2) 0.0272(8) Uani 1 1 d . . . . .
C29 C 0.6216(3) 1.1219(3) 0.7780(2) 0.0243(7) Uani 1 1 d . . . . .
C30 C 0.6124(3) 1.1345(3) 0.6874(2) 0.0267(7) Uani 1 1 d . . . . .
C31 C 0.6344(4) 1.0627(3) 0.6150(3) 0.0395(10) Uani 1 1 d . . . . .
C32 C 0.5789(3) 1.2202(3) 0.6502(2) 0.0287(8) Uani 1 1 d . . . . .
C33 C 0.8925(3) 0.8523(2) 0.6692(2) 0.0220(7) Uani 1 1 d . . . . .
C34 C 1.0055(3) 0.8738(3) 0.6335(2) 0.0255(7) Uani 1 1 d . . . . .
H34 H 1.0835 0.8933 0.6738 0.830 Uiso 1 1 calc R U . . .
C35 C 1.0036(3) 0.8665(3) 0.5383(2) 0.0288(8) Uani 1 1 d . . . . .
H35 H 1.0794 0.8829 0.5150 0.830 Uiso 1 1 calc R U . . .
C36 C 0.8861(3) 0.8341(2) 0.4780(2) 0.0242(7) Uani 1 1 d . . . . .
C37 C 0.7726(3) 0.8119(3) 0.5128(2) 0.0272(8) Uani 1 1 d . . . . .
H37 H 0.6950 0.7898 0.4725 0.830 Uiso 1 1 calc R U . . .
C38 C 0.7750(3) 0.8226(3) 0.6080(2) 0.0277(8) Uani 1 1 d . . . . .
H38 H 0.6986 0.8102 0.6313 0.830 Uiso 1 1 calc R U . . .
C39 C 0.9689(3) 0.7793(2) 0.3363(2) 0.0239(7) Uani 1 1 d . . . . .
C40 C 1.0475(3) 0.7149(3) 0.3694(2) 0.0297(8) Uani 1 1 d . . . . .
H40 H 1.0533 0.7007 0.4301 0.830 Uiso 1 1 calc R U . . .
C41 C 1.1161(3) 0.6732(3) 0.3078(2) 0.0303(8) Uani 1 1 d . . . . .
H41 H 1.1687 0.6301 0.3279 0.830 Uiso 1 1 calc R U . . .
C42 C 1.1084(4) 0.6944(3) 0.2162(2) 0.0316(8) Uani 1 1 d . . . . .
H42 H 1.1559 0.6656 0.1768 0.830 Uiso 1 1 calc R U . . .
C43 C 1.0295(3) 0.7585(3) 0.1839(2) 0.0284(8) Uani 1 1 d . . . . .
H43 H 1.0246 0.7731 0.1234 0.830 Uiso 1 1 calc R U . . .
C44 C 0.9577(3) 0.8004(2) 0.2446(2) 0.0251(7) Uani 1 1 d . . . . .
C45 C 0.8653(3) 0.8652(2) 0.2341(2) 0.0229(7) Uani 1 1 d . . . . .
C46 C 0.8207(3) 0.9154(3) 0.1613(2) 0.0283(8) Uani 1 1 d . . . . .
H46 H 0.8489 0.9078 0.1047 0.830 Uiso 1 1 calc R U . . .
C47 C 0.7348(3) 0.9758(3) 0.1758(2) 0.0295(8) Uani 1 1 d . . . . .
H47 H 0.7040 1.0092 0.1282 0.830 Uiso 1 1 calc R U . . .
C48 C 0.6923(3) 0.9883(3) 0.2614(2) 0.0280(8) Uani 1 1 d . . . . .
H48 H 0.6337 1.0296 0.2688 0.830 Uiso 1 1 calc R U . . .
C49 C 0.7354(3) 0.9405(2) 0.3356(2) 0.0261(7) Uani 1 1 d . . . . .
H49 H 0.7074 0.9489 0.3922 0.830 Uiso 1 1 calc R U . . .
C50 C 0.8230(3) 0.8791(2) 0.3200(2) 0.0239(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
N1 C9 1.145(5) . ?
N2 C10 1.145(4) . ?
N3 C32 1.153(5) . ?
N4 C31 1.117(5) . ?
N5 C28 1.408(4) . ?
N5 C14 1.410(4) . ?
N5 C17 1.415(4) . ?
N6 C39 1.388(4) . ?
N6 C50 1.398(4) . ?
N6 C36 1.413(4) . ?
C1 C2 1.374(5) . ?
C1 C6 1.401(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.395(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(5) . ?
C3 H3 0.9300 . ?
C5 C4 1.387(4) . ?
C5 C6 1.403(5) . ?
C5 H5 0.9300 . ?
C4 C7 1.479(5) . ?
C6 C29 1.486(5) . ?
C7 C8 1.364(4) . ?
C7 C33 1.470(4) . ?
C8 C9 1.433(5) . ?
C8 C10 1.440(5) . ?
C11 C16 1.397(4) . ?
C11 C12 1.412(4) . ?
C11 C29 1.482(4) . ?
C12 C13 1.388(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.404(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.398(4) . ?
C15 C16 1.391(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.392(5) . ?
C17 C22 1.403(5) . ?
C18 C19 1.402(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.404(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.390(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.400(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.441(5) . ?
C23 C24 1.398(5) . ?
C23 C28 1.403(5) . ?
C24 C25 1.393(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.394(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.401(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.393(5) . ?
C27 H27 0.9300 . ?
C29 C30 1.355(4) . ?
C30 C32 1.435(5) . ?
C30 C31 1.453(5) . ?
C33 C34 1.389(5) . ?
C33 C38 1.404(4) . ?
C34 C35 1.390(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.401(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.389(5) . ?
C37 C38 1.389(5) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 C40 1.402(5) . ?
C39 C44 1.403(5) . ?
C40 C41 1.390(5) . ?
C40 H40 0.9300 . ?
C41 C42 1.403(5) . ?
C41 H41 0.9300 . ?
C42 C43 1.398(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.407(5) . ?
C43 H43 0.9300 . ?
C44 C45 1.448(4) . ?
C45 C46 1.405(4) . ?
C45 C50 1.411(5) . ?
C46 C47 1.371(5) . ?
C46 H46 0.9300 . ?
C47 C48 1.406(5) . ?
C47 H47 0.9300 . ?
C48 C49 1.396(5) . ?
C48 H48 0.9300 . ?
C49 C50 1.398(5) . ?
C49 H49 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
C28 N5 C14 124.5(3) . . ?
C28 N5 C17 107.6(3) . . ?
C14 N5 C17 126.8(3) . . ?
C39 N6 C50 108.5(3) . . ?
C39 N6 C36 125.0(3) . . ?
C50 N6 C36 125.3(3) . . ?
C2 C1 C6 120.8(3) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 C7 120.0(3) . . ?
C3 C4 C7 119.9(3) . . ?
C1 C6 C5 118.9(3) . . ?
C1 C6 C29 119.3(3) . . ?
C5 C6 C29 121.7(3) . . ?
C8 C7 C33 121.4(3) . . ?
C8 C7 C4 120.2(3) . . ?
C33 C7 C4 118.4(3) . . ?
C7 C8 C9 124.0(3) . . ?
C7 C8 C10 122.4(3) . . ?
C9 C8 C10 113.6(3) . . ?
N1 C9 C8 175.7(4) . . ?
N2 C10 C8 174.4(4) . . ?
C16 C11 C12 118.7(3) . . ?
C16 C11 C29 122.2(3) . . ?
C12 C11 C29 119.1(3) . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 N5 120.7(3) . . ?
C13 C14 N5 119.5(3) . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C18 C17 C22 121.5(3) . . ?
C18 C17 N5 130.1(3) . . ?
C22 C17 N5 108.5(3) . . ?
C17 C18 C19 117.2(3) . . ?
C17 C18 H18 121.4 . . ?
C19 C18 H18 121.4 . . ?
C18 C19 C20 122.0(4) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C21 C20 C19 119.9(4) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 118.9(4) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C21 C22 C17 120.5(4) . . ?
C21 C22 C23 131.8(3) . . ?
C17 C22 C23 107.7(3) . . ?
C24 C23 C28 119.9(4) . . ?
C24 C23 C22 132.9(3) . . ?
C28 C23 C22 107.1(3) . . ?
C25 C24 C23 118.3(4) . . ?
C25 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
C24 C25 C26 121.4(4) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C25 C26 C27 120.8(4) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C28 C27 C26 117.5(4) . . ?
C28 C27 H27 121.2 . . ?
C26 C27 H27 121.2 . . ?
C27 C28 C23 121.9(3) . . ?
C27 C28 N5 128.8(3) . . ?
C23 C28 N5 109.1(3) . . ?
C30 C29 C11 122.3(3) . . ?
C30 C29 C6 120.9(3) . . ?
C11 C29 C6 116.9(3) . . ?
C29 C30 C32 124.4(3) . . ?
C29 C30 C31 124.4(3) . . ?
C32 C30 C31 111.2(3) . . ?
N4 C31 C30 174.2(4) . . ?
N3 C32 C30 175.6(4) . . ?
C34 C33 C38 119.3(3) . . ?
C34 C33 C7 119.5(3) . . ?
C38 C33 C7 121.2(3) . . ?
C33 C34 C35 121.0(3) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 H34 119.5 . . ?
C34 C35 C36 119.2(3) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
C37 C36 C35 120.4(3) . . ?
C37 C36 N6 121.2(3) . . ?
C35 C36 N6 118.4(3) . . ?
C36 C37 C38 120.0(3) . . ?
C36 C37 H37 120.0 . . ?
C38 C37 H37 120.0 . . ?
C37 C38 C33 120.2(3) . . ?
C37 C38 H38 119.9 . . ?
C33 C38 H38 119.9 . . ?
N6 C39 C40 128.6(3) . . ?
N6 C39 C44 109.3(3) . . ?
C40 C39 C44 122.0(3) . . ?
C41 C40 C39 117.3(3) . . ?
C41 C40 H40 121.3 . . ?
C39 C40 H40 121.3 . . ?
C40 C41 C42 121.9(3) . . ?
C40 C41 H41 119.1 . . ?
C42 C41 H41 119.1 . . ?
C43 C42 C41 120.3(3) . . ?
C43 C42 H42 119.9 . . ?
C41 C42 H42 119.9 . . ?
C42 C43 C44 118.8(3) . . ?
C42 C43 H43 120.6 . . ?
C44 C43 H43 120.6 . . ?
C39 C44 C43 119.7(3) . . ?
C39 C44 C45 106.8(3) . . ?
C43 C44 C45 133.5(3) . . ?
C46 C45 C50 119.9(3) . . ?
C46 C45 C44 133.3(3) . . ?
C50 C45 C44 106.8(3) . . ?
C47 C46 C45 118.4(3) . . ?
C47 C46 H46 120.8 . . ?
C45 C46 H46 120.8 . . ?
C46 C47 C48 121.2(3) . . ?
C46 C47 H47 119.4 . . ?
C48 C47 H47 119.4 . . ?
C49 C48 C47 122.0(3) . . ?
C49 C48 H48 119.0 . . ?
C47 C48 H48 119.0 . . ?
C48 C49 C50 116.3(3) . . ?
C48 C49 H49 121.8 . . ?
C50 C49 H49 121.8 . . ?
C49 C50 N6 129.1(3) . . ?
C49 C50 C45 122.2(3) . . ?
N6 C50 C45 108.6(3) . . ?

_refine_diff_density_max         0.695
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.104
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.021 0.500 0.500 411 143 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1942677'
loop_
_audit_author_name
_audit_author_address
'Zhiyong Guo'
;Fuzhou University
China
;
_audit_update_record             
;
2019-07-23 deposited with the CCDC.	2020-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C26 H16 Cl2 N3'
_chemical_formula_sum            'C26 H16 Cl2 N3'
_chemical_formula_weight         441.32

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'
Cl Cl 0.1484 0.1585 '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                   9.681(3)
_cell_length_b                   10.530(3)
_cell_length_c                   12.299(3)
_cell_angle_alpha                65.887(5)
_cell_angle_beta                 70.323(5)
_cell_angle_gamma                85.583(6)
_cell_volume                     1074.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5400
_cell_measurement_theta_min      1.926
_cell_measurement_theta_max      28.549

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             454
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.321
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8123
_diffrn_reflns_av_unetI/netI     0.0758
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.926
_diffrn_reflns_theta_max         28.549
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5400
_reflns_number_gt                3923
_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 (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)+(0.1291P)²+0.3593P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5400
_refine_ls_number_parameters     288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.2165
_refine_ls_wR_factor_gt          0.1843
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
N1 N -0.4129(2) -0.2476(2) 0.2277(2) 0.0186(5) Uani 1 1 d . . . . .
N2 N -0.9739(3) -1.0672(2) 0.6427(2) 0.0289(6) Uani 1 1 d . . . . .
N3 N -1.0435(3) -0.6421(2) 0.4481(2) 0.0259(5) Uani 1 1 d . . . . .
C1 C -0.2663(3) -0.2312(3) 0.2170(2) 0.0168(5) Uani 1 1 d . . . . .
C2 C -0.1684(3) -0.3320(3) 0.2508(2) 0.0201(5) Uani 1 1 d . . . . .
H2 H -0.1962 -0.4267 0.2854 0.080 Uiso 1 1 calc R U . . .
C3 C -0.0282(3) -0.2853(3) 0.2307(3) 0.0241(6) Uani 1 1 d . . . . .
H3 H 0.0396 -0.3502 0.2518 0.080 Uiso 1 1 calc R U . . .
C4 C 0.0135(3) -0.1438(3) 0.1798(3) 0.0272(6) Uani 1 1 d . . . . .
H4 H 0.1090 -0.1159 0.1658 0.080 Uiso 1 1 calc R U . . .
C5 C -0.0848(3) -0.0438(3) 0.1495(3) 0.0234(6) Uani 1 1 d . . . . .
H5 H -0.0569 0.0506 0.1171 0.080 Uiso 1 1 calc R U . . .
C6 C -0.2268(3) -0.0878(3) 0.1686(2) 0.0180(5) Uani 1 1 d . . . . .
C7 C -0.3543(3) -0.0145(3) 0.1497(2) 0.0190(5) Uani 1 1 d . . . . .
C8 C -0.3809(3) 0.1266(3) 0.1035(3) 0.0251(6) Uani 1 1 d . . . . .
H8 H -0.3073 0.1947 0.0779 0.080 Uiso 1 1 calc R U . . .
C9 C -0.5197(4) 0.1632(3) 0.0964(3) 0.0302(7) Uani 1 1 d . . . . .
H9 H -0.5396 0.2568 0.0670 0.080 Uiso 1 1 calc R U . . .
C10 C -0.6285(3) 0.0621(3) 0.1326(3) 0.0299(7) Uani 1 1 d . . . . .
H10 H -0.7201 0.0894 0.1260 0.080 Uiso 1 1 calc R U . . .
C11 C -0.6048(3) -0.0788(3) 0.1785(3) 0.0248(6) Uani 1 1 d . . . . .
H11 H -0.6784 -0.1463 0.2025 0.080 Uiso 1 1 calc R U . . .
C12 C -0.4669(3) -0.1151(3) 0.1873(2) 0.0184(5) Uani 1 1 d . . . . .
C13 C -0.4927(3) -0.3773(2) 0.2781(2) 0.0164(5) Uani 1 1 d . . . . .
C14 C -0.6305(3) -0.4043(3) 0.3717(2) 0.0189(5) Uani 1 1 d . . . . .
H14 H -0.6736 -0.3347 0.3973 0.080 Uiso 1 1 calc R U . . .
C15 C -0.7028(3) -0.5348(3) 0.4263(2) 0.0176(5) Uani 1 1 d . . . . .
H15 H -0.7960 -0.5516 0.4868 0.080 Uiso 1 1 calc R U . . .
C16 C -0.6378(3) -0.6423(2) 0.3917(2) 0.0163(5) Uani 1 1 d . . . . .
C17 C -0.5010(3) -0.6122(3) 0.2947(2) 0.0190(5) Uani 1 1 d . . . . .
H17 H -0.4575 -0.6817 0.2690 0.080 Uiso 1 1 calc R U . . .
C18 C -0.4303(3) -0.4810(3) 0.2371(2) 0.0194(5) Uani 1 1 d . . . . .
H18 H -0.3412 -0.4614 0.1711 0.080 Uiso 1 1 calc R U . . .
C19 C -0.7038(3) -0.7863(2) 0.4582(2) 0.0165(5) Uani 1 1 d . . . . .
C20 C -0.8514(3) -0.8186(3) 0.5012(2) 0.0181(5) Uani 1 1 d . . . . .
C21 C -0.9565(3) -0.7181(3) 0.4721(2) 0.0190(5) Uani 1 1 d . . . . .
C22 C -0.9165(3) -0.9589(3) 0.5801(3) 0.0213(5) Uani 1 1 d . . . . .
C23 C -0.6005(3) -0.8973(2) 0.4802(2) 0.0162(5) Uani 1 1 d . . . . .
C24 C -0.4916(3) -0.8860(3) 0.5271(2) 0.0187(5) Uani 1 1 d . . . . .
H24 H -0.4860 -0.8094 0.5452 0.080 Uiso 1 1 calc R U . . .
C25 C -0.3916(3) -0.9871(3) 0.5472(3) 0.0198(5) Uani 1 1 d . . . . .
H25 H -0.3196 -0.9784 0.5786 0.080 Uiso 1 1 calc R U . . .
C26 C -0.0933(5) -0.3855(4) -0.1502(3) 0.0462(10) Uani 1 1 d . . . . .
Cl1 Cl -0.25657(10) -0.48879(10) -0.09595(10) 0.0456(3) Uani 1 1 d . . . . .
Cl2 Cl -0.07966(10) -0.33121(8) -0.03588(7) 0.0373(2) Uani 1 1 d . . . . .
H26A H -0.079(5) -0.316(5) -0.225(5) 0.062(14) Uiso 1 1 d . . . . .
H26B H -0.005(5) -0.446(5) -0.171(4) 0.060(13) 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
N1 C1 1.398(3) . ?
N1 C12 1.400(3) . ?
N1 C13 1.412(3) . ?
N2 C22 1.137(4) . ?
N3 C21 1.143(3) . ?
C1 C2 1.395(4) . ?
C1 C6 1.407(3) . ?
C2 C3 1.387(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.441(4) . ?
C7 C8 1.394(4) . ?
C7 C12 1.401(4) . ?
C8 C9 1.391(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.387(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(4) . ?
C11 H11 0.9300 . ?
C13 C14 1.394(3) . ?
C13 C18 1.398(3) . ?
C14 C15 1.381(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.401(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.402(3) . ?
C16 C19 1.470(3) . ?
C17 C18 1.378(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.363(4) . ?
C19 C23 1.478(3) . ?
C20 C21 1.433(4) . ?
C20 C22 1.443(4) . ?
C23 C24 1.394(4) . ?
C23 C25 1.402(3) 2_436 ?
C24 C25 1.385(3) . ?
C24 H24 0.9300 . ?
C25 C23 1.402(3) 2_436 ?
C25 H25 0.9300 . ?
C26 Cl1 1.757(4) . ?
C26 Cl2 1.765(4) . ?
C26 H26A 0.88(5) . ?
C26 H26B 1.05(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
C1 N1 C12 108.3(2) . . ?
C1 N1 C13 124.8(2) . . ?
C12 N1 C13 126.8(2) . . ?
C2 C1 N1 129.7(2) . . ?
C2 C1 C6 121.6(2) . . ?
N1 C1 C6 108.6(2) . . ?
C3 C2 C1 117.3(2) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 118.5(3) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 C7 133.1(2) . . ?
C1 C6 C7 107.1(2) . . ?
C8 C7 C12 119.6(2) . . ?
C8 C7 C6 133.3(3) . . ?
C12 C7 C6 107.1(2) . . ?
C9 C8 C7 118.6(3) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 121.8(3) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C12 117.4(3) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C11 C12 N1 129.3(2) . . ?
C11 C12 C7 121.9(2) . . ?
N1 C12 C7 108.8(2) . . ?
C14 C13 C18 119.9(2) . . ?
C14 C13 N1 120.5(2) . . ?
C18 C13 N1 119.6(2) . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C17 118.4(2) . . ?
C15 C16 C19 122.2(2) . . ?
C17 C16 C19 119.3(2) . . ?
C18 C17 C16 120.9(2) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C13 119.9(2) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C20 C19 C16 123.2(2) . . ?
C20 C19 C23 120.7(2) . . ?
C16 C19 C23 116.1(2) . . ?
C19 C20 C21 123.7(2) . . ?
C19 C20 C22 122.7(2) . . ?
C21 C20 C22 113.6(2) . . ?
N3 C21 C20 177.0(3) . . ?
N2 C22 C20 176.9(3) . . ?
C24 C23 C25 119.3(2) . 2_436 ?
C24 C23 C19 119.5(2) . . ?
C25 C23 C19 121.2(2) 2_436 . ?
C25 C24 C23 121.0(2) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C23 119.7(2) . 2_436 ?
C24 C25 H25 120.2 . . ?
C23 C25 H25 120.2 2_436 . ?
Cl1 C26 Cl2 112.0(2) . . ?
Cl1 C26 H26A 113(3) . . ?
Cl2 C26 H26A 113(3) . . ?
Cl1 C26 H26B 108(2) . . ?
Cl2 C26 H26B 109(3) . . ?
H26A C26 H26B 102(4) . . ?

_refine_diff_density_max         1.420
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.115

_shelxl_version_number           2014-1

