# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_ic19946_sq
_database_code_depnum_ccdc_archive 'CCDC 2153889'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung Liu'
;Instrumentation Center, National Taiwan University 
Taiwan
;
_audit_update_record             
;
2022-02-22 deposited with the CCDC.	2022-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H31 N3'
_chemical_formula_weight         613.73

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                   9.7546(3)
_cell_length_b                   10.8555(3)
_cell_length_c                   17.1955(5)
_cell_angle_alpha                97.964(2)
_cell_angle_beta                 92.592(2)
_cell_angle_gamma                115.717(3)
_cell_volume                     1613.31(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3529
_cell_measurement_theta_min      3.4370
_cell_measurement_theta_max      27.3820

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94534
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_reflns_number            13449
_diffrn_reflns_av_unetI/netI     0.0925
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.913
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7149
_reflns_number_gt                4255
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0680P)²+0.8177P] 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         7149
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1658
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_restrained_S_all      0.924
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6464(2) 0.4641(2) 0.45852(11) 0.0241(5) Uani 1 1 d . . . . .
N2 N 0.2490(2) -0.0073(2) 0.10091(13) 0.0353(5) Uani 1 1 d . . . . .
N3 N 0.4796(2) 0.1785(2) 0.11319(12) 0.0301(5) Uani 1 1 d . . . . .
C1 C 0.7067(2) 0.6082(2) 0.47099(14) 0.0245(5) Uani 1 1 d . . . . .
C2 C 0.7925(3) 0.7032(3) 0.53833(14) 0.0265(6) Uani 1 1 d . . . . .
H2A H 0.818696 0.673764 0.583851 0.032 Uiso 1 1 calc R U . . .
C3 C 0.8378(3) 0.8420(3) 0.53625(15) 0.0296(6) Uani 1 1 d . . . . .
H3A H 0.893809 0.909081 0.581889 0.035 Uiso 1 1 calc R U . . .
C4 C 0.8035(3) 0.8861(3) 0.46871(16) 0.0310(6) Uani 1 1 d . . . . .
H4A H 0.839170 0.982616 0.468598 0.037 Uiso 1 1 calc R U . . .
C5 C 0.7183(3) 0.7912(3) 0.40197(15) 0.0280(6) Uani 1 1 d . . . . .
H5A H 0.695457 0.821806 0.356132 0.034 Uiso 1 1 calc R U . . .
C6 C 0.6662(3) 0.6494(2) 0.40294(14) 0.0239(5) Uani 1 1 d . . . . .
C7 C 0.5678(2) 0.5233(2) 0.34859(14) 0.0230(5) Uani 1 1 d . . . . .
C8 C 0.4776(3) 0.4974(3) 0.27746(14) 0.0262(5) Uani 1 1 d . . . . .
H8A H 0.482509 0.572230 0.253012 0.031 Uiso 1 1 calc R U . . .
C9 C 0.3804(3) 0.3610(3) 0.24250(14) 0.0254(5) Uani 1 1 d . . . . .
C10 C 0.3768(3) 0.2517(3) 0.27961(14) 0.0267(5) Uani 1 1 d . . . . .
H10A H 0.310195 0.158833 0.255381 0.032 Uiso 1 1 calc R U . . .
C11 C 0.4660(3) 0.2741(3) 0.34972(14) 0.0262(5) Uani 1 1 d . . . . .
H11A H 0.463427 0.198959 0.373151 0.031 Uiso 1 1 calc R U . . .
C12 C 0.5596(3) 0.4113(2) 0.38450(13) 0.0236(5) Uani 1 1 d . . . . .
C13 C 0.6704(3) 0.3916(2) 0.51557(14) 0.0248(5) Uani 1 1 d . . . . .
H13A H 0.639604 0.406462 0.566260 0.030 Uiso 1 1 calc R U . . .
C14 C 0.7329(2) 0.3035(2) 0.50400(14) 0.0221(5) Uani 1 1 d . . . . .
C15 C 0.7502(3) 0.2358(2) 0.57071(14) 0.0232(5) Uani 1 1 d . . . . .
C16 C 0.6381(3) 0.1927(3) 0.62157(15) 0.0321(6) Uani 1 1 d . . . . .
H16A H 0.544178 0.196751 0.609998 0.039 Uiso 1 1 calc R U . . .
C17 C 0.6615(3) 0.1438(3) 0.68907(16) 0.0356(6) Uani 1 1 d . . . . .
H17A H 0.583550 0.114699 0.723064 0.043 Uiso 1 1 calc R U . . .
C18 C 0.7971(3) 0.1373(2) 0.70691(15) 0.0290(6) Uani 1 1 d . . . . .
H18A H 0.814253 0.106445 0.753817 0.035 Uiso 1 1 calc R U . . .
C19 C 0.9079(3) 0.1763(2) 0.65577(14) 0.0268(6) Uani 1 1 d . . . . .
H19A H 1.000892 0.170439 0.667203 0.032 Uiso 1 1 calc R U . . .
C20 C 0.8846(3) 0.2238(2) 0.58808(14) 0.0241(5) Uani 1 1 d . . . . .
H20A H 0.961025 0.248527 0.553023 0.029 Uiso 1 1 calc R U . . .
C21 C 0.7961(3) 0.2800(2) 0.42926(13) 0.0226(5) Uani 1 1 d . . . . .
C22 C 0.7517(3) 0.1467(3) 0.38773(14) 0.0275(6) Uani 1 1 d . . . . .
H22A H 0.676962 0.069116 0.406127 0.033 Uiso 1 1 calc R U . . .
C23 C 0.8158(3) 0.1258(3) 0.31961(15) 0.0323(6) Uani 1 1 d . . . . .
H23A H 0.783181 0.034414 0.291205 0.039 Uiso 1 1 calc R U . . .
C24 C 0.9266(3) 0.2374(3) 0.29294(15) 0.0327(6) Uani 1 1 d . . . . .
H24A H 0.971789 0.222630 0.246960 0.039 Uiso 1 1 calc R U . . .
C25 C 0.9717(3) 0.3709(3) 0.33350(14) 0.0290(6) Uani 1 1 d . . . . .
H25A H 1.047565 0.447880 0.315149 0.035 Uiso 1 1 calc R U . . .
C26 C 0.9064(3) 0.3925(3) 0.40071(14) 0.0260(5) Uani 1 1 d . . . . .
H26A H 0.936615 0.484443 0.427721 0.031 Uiso 1 1 calc R U . . .
C27 C 0.2751(3) 0.3310(3) 0.16899(14) 0.0279(6) Uani 1 1 d . . . . .
C28 C 0.1988(3) 0.4128(3) 0.16176(15) 0.0304(6) Uani 1 1 d . . . . .
H28A H 0.223232 0.492346 0.200963 0.037 Uiso 1 1 calc R U . . .
C29 C 0.0882(3) 0.3805(3) 0.09872(16) 0.0370(7) Uani 1 1 d . . . . .
H29A H 0.037570 0.437533 0.095243 0.044 Uiso 1 1 calc R U . . .
C30 C 0.0513(3) 0.2650(3) 0.04068(16) 0.0400(7) Uani 1 1 d . . . . .
H30A H -0.026804 0.240649 -0.001691 0.048 Uiso 1 1 calc R U . . .
C31 C 0.1296(3) 0.1858(3) 0.04529(15) 0.0346(6) Uani 1 1 d . . . . .
H31A H 0.106047 0.107866 0.005056 0.042 Uiso 1 1 calc R U . . .
C32 C 0.2428(3) 0.2183(3) 0.10811(14) 0.0301(6) Uani 1 1 d . . . . .
C33 C 0.3213(3) 0.1285(3) 0.10721(14) 0.0309(6) Uani 1 1 d . . . . .
C34 C 0.3636(3) -0.0506(3) 0.10399(15) 0.0368(6) Uani 1 1 d . . . . .
C35 C 0.3515(4) -0.1838(3) 0.10248(17) 0.0468(8) Uani 1 1 d . . . . .
H35A H 0.254419 -0.262291 0.097299 0.056 Uiso 1 1 calc R U . . .
C36 C 0.4855(4) -0.1975(3) 0.10876(17) 0.0519(9) Uani 1 1 d . . . . .
H36A H 0.480129 -0.286791 0.109708 0.062 Uiso 1 1 calc R U . . .
C37 C 0.6281(4) -0.0841(3) 0.11373(17) 0.0497(8) Uani 1 1 d . . . . .
H37A H 0.717593 -0.098305 0.116258 0.060 Uiso 1 1 calc R U . . .
C38 C 0.6433(3) 0.0496(3) 0.11510(16) 0.0422(7) Uani 1 1 d . . . . .
H38A H 0.740652 0.127136 0.118145 0.051 Uiso 1 1 calc R U . . .
C39 C 0.5082(3) 0.0634(3) 0.11177(14) 0.0332(6) Uani 1 1 d . . . . .
C40 C 0.5930(3) 0.3201(3) 0.12405(15) 0.0299(6) Uani 1 1 d . . . . .
C41 C 0.7084(3) 0.3717(3) 0.18649(15) 0.0312(6) Uani 1 1 d . . . . .
H41A H 0.713435 0.312995 0.221572 0.037 Uiso 1 1 calc R U . . .
C42 C 0.8167(3) 0.5091(3) 0.19761(16) 0.0350(6) Uani 1 1 d . . . . .
H42A H 0.896317 0.544620 0.240367 0.042 Uiso 1 1 calc R U . . .
C43 C 0.8098(3) 0.5953(3) 0.14695(17) 0.0396(7) Uani 1 1 d . . . . .
H43A H 0.884233 0.689680 0.154820 0.048 Uiso 1 1 calc R U . . .
C44 C 0.6937(3) 0.5429(3) 0.08476(17) 0.0401(7) Uani 1 1 d . . . . .
H44A H 0.688821 0.601949 0.049918 0.048 Uiso 1 1 calc R U . . .
C45 C 0.5854(3) 0.4065(3) 0.07272(15) 0.0352(6) Uani 1 1 d . . . . .
H45A H 0.506017 0.371367 0.029842 0.042 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
N1 C1 1.391(3) . ?
N1 C12 1.394(3) . ?
N1 C13 1.410(3) . ?
N2 C33 1.315(3) . ?
N2 C34 1.390(3) . ?
N3 C33 1.390(3) . ?
N3 C39 1.391(3) . ?
N3 C40 1.430(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.408(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.396(4) . ?
C4 C5 1.383(3) . ?
C5 C6 1.398(3) . ?
C6 C7 1.447(3) . ?
C7 C8 1.393(3) . ?
C7 C12 1.412(3) . ?
C8 C9 1.391(3) . ?
C9 C10 1.411(3) . ?
C9 C27 1.496(3) . ?
C10 C11 1.382(3) . ?
C11 C12 1.390(3) . ?
C13 C14 1.338(3) . ?
C14 C21 1.488(3) . ?
C14 C15 1.486(3) . ?
C15 C16 1.391(3) . ?
C15 C20 1.396(3) . ?
C16 C17 1.390(4) . ?
C17 C18 1.378(3) . ?
C18 C19 1.383(3) . ?
C19 C20 1.384(3) . ?
C21 C22 1.391(3) . ?
C21 C26 1.401(3) . ?
C22 C23 1.389(3) . ?
C23 C24 1.382(4) . ?
C24 C25 1.386(4) . ?
C25 C26 1.385(3) . ?
C27 C28 1.398(3) . ?
C27 C32 1.405(3) . ?
C28 C29 1.387(3) . ?
C29 C30 1.388(4) . ?
C30 C31 1.382(4) . ?
C31 C32 1.400(3) . ?
C32 C33 1.477(4) . ?
C34 C35 1.395(4) . ?
C34 C39 1.401(4) . ?
C35 C36 1.379(4) . ?
C36 C37 1.391(5) . ?
C37 C38 1.390(4) . ?
C38 C39 1.389(4) . ?
C40 C41 1.383(3) . ?
C40 C45 1.396(4) . ?
C41 C42 1.383(4) . ?
C42 C43 1.383(4) . ?
C43 C44 1.383(4) . ?
C44 C45 1.375(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 108.37(19) . . ?
C1 N1 C13 122.65(19) . . ?
C12 N1 C13 128.9(2) . . ?
C33 N2 C34 105.3(2) . . ?
C33 N3 C39 106.3(2) . . ?
C33 N3 C40 127.8(2) . . ?
C39 N3 C40 125.9(2) . . ?
C2 C1 N1 128.4(2) . . ?
C2 C1 C6 122.4(2) . . ?
N1 C1 C6 109.3(2) . . ?
C3 C2 C1 117.2(2) . . ?
C2 C3 C4 121.6(2) . . ?
C5 C4 C3 120.8(2) . . ?
C4 C5 C6 119.0(2) . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 134.6(2) . . ?
C1 C6 C7 106.5(2) . . ?
C8 C7 C12 119.8(2) . . ?
C8 C7 C6 133.0(2) . . ?
C12 C7 C6 106.9(2) . . ?
C9 C8 C7 119.5(2) . . ?
C8 C9 C10 119.1(2) . . ?
C8 C9 C27 120.4(2) . . ?
C10 C9 C27 120.4(2) . . ?
C11 C10 C9 122.7(2) . . ?
C10 C11 C12 117.2(2) . . ?
C11 C12 N1 129.3(2) . . ?
C11 C12 C7 121.7(2) . . ?
N1 C12 C7 108.8(2) . . ?
C14 C13 N1 125.2(2) . . ?
C13 C14 C21 122.3(2) . . ?
C13 C14 C15 118.3(2) . . ?
C21 C14 C15 119.21(19) . . ?
C16 C15 C20 117.9(2) . . ?
C16 C15 C14 120.9(2) . . ?
C20 C15 C14 121.0(2) . . ?
C15 C16 C17 121.0(2) . . ?
C18 C17 C16 120.3(2) . . ?
C17 C18 C19 119.3(2) . . ?
C20 C19 C18 120.6(2) . . ?
C19 C20 C15 120.8(2) . . ?
C22 C21 C26 118.5(2) . . ?
C22 C21 C14 121.2(2) . . ?
C26 C21 C14 120.3(2) . . ?
C21 C22 C23 120.6(2) . . ?
C24 C23 C22 120.3(2) . . ?
C23 C24 C25 119.7(2) . . ?
C26 C25 C24 120.2(2) . . ?
C25 C26 C21 120.6(2) . . ?
C28 C27 C32 118.1(2) . . ?
C28 C27 C9 119.4(2) . . ?
C32 C27 C9 122.4(2) . . ?
C29 C28 C27 121.6(2) . . ?
C30 C29 C28 120.1(3) . . ?
C31 C30 C29 119.2(2) . . ?
C30 C31 C32 121.3(3) . . ?
C31 C32 C27 119.7(2) . . ?
C31 C32 C33 117.2(2) . . ?
C27 C32 C33 123.1(2) . . ?
N2 C33 N3 112.8(2) . . ?
N2 C33 C32 123.6(2) . . ?
N3 C33 C32 123.6(2) . . ?
N2 C34 C35 129.6(3) . . ?
N2 C34 C39 110.4(2) . . ?
C35 C34 C39 120.0(3) . . ?
C36 C35 C34 117.7(3) . . ?
C35 C36 C37 121.7(3) . . ?
C36 C37 C38 121.7(3) . . ?
C39 C38 C37 116.2(3) . . ?
C38 C39 N3 132.2(3) . . ?
C38 C39 C34 122.5(3) . . ?
N3 C39 C34 105.3(2) . . ?
C41 C40 C45 120.1(2) . . ?
C41 C40 N3 119.7(2) . . ?
C45 C40 N3 120.1(2) . . ?
C40 C41 C42 119.7(3) . . ?
C43 C42 C41 120.5(2) . . ?
C44 C43 C42 119.5(3) . . ?
C45 C44 C43 120.8(3) . . ?
C44 C45 C40 119.4(2) . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.052



####################################################################### 
# 
# 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_ic20275-twin
_database_code_depnum_ccdc_archive 'CCDC 2153890'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung Liu'
;Instrumentation Center, National Taiwan University 
Taiwan
;
_audit_update_record             
;
2022-02-22 deposited with the CCDC.	2022-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H31 N3'
_chemical_formula_weight         613.73

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                   8.9933(13)
_cell_length_b                   9.9705(15)
_cell_length_c                   19.962(3)
_cell_angle_alpha                82.180(12)
_cell_angle_beta                 81.467(12)
_cell_angle_gamma                63.224(14)
_cell_volume                     1575.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2837
_cell_measurement_theta_min      3.7430
_cell_measurement_theta_max      29.3880

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82855
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_reflns_number            10313
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_av_R_equivalents  0.1505
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.844
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             10313
_reflns_number_gt                6857
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)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         10313
_refine_ls_number_parameters     434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1110
_refine_ls_R_factor_gt           0.0741
_refine_ls_wR_factor_ref         0.2208
_refine_ls_wR_factor_gt          0.1969
_refine_ls_goodness_of_fit_ref   1.356
_refine_ls_restrained_S_all      1.356
_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 0.5788(3) 0.6480(3) 0.04358(15) 0.0290(7) Uani 1 1 d . . . . .
N2 N 0.8236(4) 0.4416(3) 0.05913(16) 0.0319(7) Uani 1 1 d . . . . .
N3 N 0.6209(3) 0.6340(3) 0.58602(16) 0.0338(7) Uani 1 1 d . . . . .
C1 C 0.6404(4) 0.5890(4) -0.01933(18) 0.0284(8) Uani 1 1 d . . . . .
C2 C 0.5792(5) 0.6306(4) -0.08252(19) 0.0317(8) Uani 1 1 d . . . . .
H2A H 0.473874 0.714057 -0.088858 0.038 Uiso 1 1 calc R U . . .
C3 C 0.6765(5) 0.5467(4) -0.13590(19) 0.0344(9) Uani 1 1 d . . . . .
H3A H 0.636751 0.573284 -0.179581 0.041 Uiso 1 1 calc R U . . .
C4 C 0.8303(5) 0.4250(4) -0.1275(2) 0.0387(10) Uani 1 1 d . . . . .
H4A H 0.894537 0.370327 -0.165360 0.046 Uiso 1 1 calc R U . . .
C5 C 0.8917(5) 0.3819(4) -0.0643(2) 0.0374(9) Uani 1 1 d . . . . .
H5A H 0.997805 0.299038 -0.058602 0.045 Uiso 1 1 calc R U . . .
C6 C 0.7938(4) 0.4632(4) -0.00908(19) 0.0301(8) Uani 1 1 d . . . . .
C7 C 0.4586(4) 0.8002(4) 0.05237(17) 0.0280(8) Uani 1 1 d . . . . .
C8 C 0.3024(4) 0.8571(4) 0.0304(2) 0.0378(9) Uani 1 1 d . . . . .
H8A H 0.271265 0.794348 0.009709 0.045 Uiso 1 1 calc R U . . .
C9 C 0.1909(5) 1.0056(4) 0.0384(2) 0.0448(11) Uani 1 1 d . . . . .
H9A H 0.084879 1.045593 0.021238 0.054 Uiso 1 1 calc R U . . .
C10 C 0.2305(5) 1.0970(4) 0.0708(2) 0.0477(11) Uani 1 1 d . . . . .
H10A H 0.151123 1.198029 0.077581 0.057 Uiso 1 1 calc R U . . .
C11 C 0.3859(5) 1.0401(4) 0.0933(2) 0.0419(10) Uani 1 1 d . . . . .
H11A H 0.414757 1.102394 0.115465 0.050 Uiso 1 1 calc R U . . .
C12 C 0.5007(5) 0.8933(4) 0.08389(18) 0.0321(9) Uani 1 1 d . . . . .
H12A H 0.608798 0.855277 0.098927 0.039 Uiso 1 1 calc R U . . .
C13 C 0.6951(4) 0.5524(4) 0.08894(19) 0.0297(8) Uani 1 1 d . . . . .
C14 C 0.6738(4) 0.5662(4) 0.16205(19) 0.0300(8) Uani 1 1 d . . . . .
C15 C 0.8148(4) 0.5006(4) 0.19868(19) 0.0318(9) Uani 1 1 d . . . . .
H15A H 0.922576 0.449678 0.175272 0.038 Uiso 1 1 calc R U . . .
C16 C 0.8003(4) 0.5085(4) 0.26799(19) 0.0311(8) Uani 1 1 d . . . . .
H16A H 0.898707 0.463757 0.290987 0.037 Uiso 1 1 calc R U . . .
C17 C 0.6442(4) 0.5808(4) 0.30558(18) 0.0287(8) Uani 1 1 d . . . . .
C18 C 0.5034(4) 0.6424(4) 0.26869(19) 0.0312(8) Uani 1 1 d . . . . .
H18A H 0.395078 0.689723 0.292249 0.037 Uiso 1 1 calc R U . . .
C19 C 0.5177(5) 0.6361(4) 0.1995(2) 0.0330(9) Uani 1 1 d . . . . .
H19A H 0.419293 0.680298 0.176509 0.040 Uiso 1 1 calc R U . . .
C20 C 0.6037(4) 0.6329(4) 0.51827(19) 0.0314(8) Uani 1 1 d . . . . .
C21 C 0.4769(5) 0.7341(4) 0.4790(2) 0.0399(10) Uani 1 1 d . . . . .
H21A H 0.382430 0.815884 0.498511 0.048 Uiso 1 1 calc R U . . .
C22 C 0.4921(4) 0.7123(4) 0.4113(2) 0.0371(9) Uani 1 1 d . . . . .
H22A H 0.406213 0.780966 0.384259 0.045 Uiso 1 1 calc R U . . .
C23 C 0.6295(4) 0.5927(4) 0.38039(19) 0.0304(8) Uani 1 1 d . . . . .
C24 C 0.7540(4) 0.4923(4) 0.42064(18) 0.0306(8) Uani 1 1 d . . . . .
H24A H 0.847911 0.410240 0.401078 0.037 Uiso 1 1 calc R U . . .
C25 C 0.7417(4) 0.5114(4) 0.48906(18) 0.0301(8) Uani 1 1 d . . . . .
C26 C 0.8476(4) 0.4310(4) 0.54406(18) 0.0295(8) Uani 1 1 d . . . . .
C27 C 0.9975(5) 0.3007(4) 0.5473(2) 0.0403(10) Uani 1 1 d . . . . .
H27A H 1.053630 0.247997 0.508009 0.048 Uiso 1 1 calc R U . . .
C28 C 1.0628(5) 0.2496(4) 0.6097(2) 0.0426(10) Uani 1 1 d . . . . .
H28A H 1.165015 0.160691 0.612828 0.051 Uiso 1 1 calc R U . . .
C29 C 0.9825(5) 0.3254(4) 0.6676(2) 0.0406(10) Uani 1 1 d . . . . .
H29A H 1.029334 0.286548 0.709723 0.049 Uiso 1 1 calc R U . . .
C30 C 0.8351(4) 0.4567(4) 0.66475(19) 0.0337(9) Uani 1 1 d . . . . .
H30A H 0.780817 0.510584 0.703904 0.040 Uiso 1 1 calc R U . . .
C31 C 0.7696(4) 0.5068(4) 0.60238(19) 0.0300(8) Uani 1 1 d . . . . .
C32 C 0.4972(4) 0.7264(4) 0.63432(19) 0.0343(9) Uani 1 1 d . . . . .
H32A H 0.389219 0.729348 0.638195 0.041 Uiso 1 1 calc R U . . .
C33 C 0.5218(4) 0.8094(4) 0.67470(18) 0.0280(8) Uani 1 1 d . . . . .
C34 C 0.6738(4) 0.8380(4) 0.6684(2) 0.0324(9) Uani 1 1 d . . . . .
C35 C 0.7360(5) 0.8827(4) 0.6056(2) 0.0404(10) Uani 1 1 d . . . . .
H35A H 0.689221 0.885661 0.565442 0.048 Uiso 1 1 calc R U . . .
C36 C 0.8675(5) 0.9233(4) 0.6018(3) 0.0521(12) Uani 1 1 d . . . . .
H36A H 0.909452 0.954738 0.559211 0.063 Uiso 1 1 calc R U . . .
C37 C 0.9366(5) 0.9174(5) 0.6609(3) 0.0528(12) Uani 1 1 d . . . . .
H37A H 1.025319 0.945463 0.658525 0.063 Uiso 1 1 calc R U . . .
C38 C 0.8780(5) 0.8721(5) 0.7215(3) 0.0584(13) Uani 1 1 d . . . . .
H38A H 0.926690 0.867088 0.761458 0.070 Uiso 1 1 calc R U . . .
C39 C 0.7472(5) 0.8329(4) 0.7258(2) 0.0395(10) Uani 1 1 d . . . . .
H39A H 0.706828 0.801911 0.768914 0.047 Uiso 1 1 calc R U . . .
C40 C 0.3923(4) 0.8808(4) 0.73138(18) 0.0272(8) Uani 1 1 d . . . . .
C41 C 0.3532(4) 1.0251(4) 0.74759(19) 0.0317(9) Uani 1 1 d . . . . .
H41A H 0.409324 1.079379 0.722006 0.038 Uiso 1 1 calc R U . . .
C42 C 0.2342(4) 1.0904(4) 0.8002(2) 0.0352(9) Uani 1 1 d . . . . .
H42A H 0.207305 1.189757 0.810157 0.042 Uiso 1 1 calc R U . . .
C43 C 0.1536(5) 1.0113(4) 0.8387(2) 0.0374(9) Uani 1 1 d . . . . .
H43A H 0.072280 1.055937 0.875292 0.045 Uiso 1 1 calc R U . . .
C44 C 0.1919(4) 0.8684(4) 0.82380(19) 0.0343(9) Uani 1 1 d . . . . .
H44A H 0.136926 0.813991 0.850176 0.041 Uiso 1 1 calc R U . . .
C45 C 0.3107(4) 0.8026(4) 0.77034(19) 0.0306(8) Uani 1 1 d . . . . .
H45B H 0.336210 0.703596 0.760338 0.037 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.390(4) . ?
N1 C13 1.404(4) . ?
N1 C7 1.429(4) . ?
N2 C13 1.317(4) . ?
N2 C6 1.396(5) . ?
N3 C20 1.386(5) . ?
N3 C31 1.412(4) . ?
N3 C32 1.420(4) . ?
C1 C2 1.387(5) . ?
C1 C6 1.404(5) . ?
C2 C3 1.381(5) . ?
C3 C4 1.384(5) . ?
C4 C5 1.388(5) . ?
C5 C6 1.400(5) . ?
C7 C8 1.372(5) . ?
C7 C12 1.395(5) . ?
C8 C9 1.380(5) . ?
C9 C10 1.378(6) . ?
C10 C11 1.371(6) . ?
C11 C12 1.379(5) . ?
C13 C14 1.461(5) . ?
C14 C19 1.402(5) . ?
C14 C15 1.403(5) . ?
C15 C16 1.380(5) . ?
C16 C17 1.406(5) . ?
C17 C18 1.406(5) . ?
C17 C23 1.496(5) . ?
C18 C19 1.375(5) . ?
C20 C21 1.395(5) . ?
C20 C25 1.404(5) . ?
C21 C22 1.375(5) . ?
C22 C23 1.406(5) . ?
C23 C24 1.392(5) . ?
C24 C25 1.386(5) . ?
C25 C26 1.462(5) . ?
C26 C27 1.391(5) . ?
C26 C31 1.392(5) . ?
C27 C28 1.390(5) . ?
C28 C29 1.388(6) . ?
C29 C30 1.383(5) . ?
C30 C31 1.389(5) . ?
C32 C33 1.335(5) . ?
C33 C40 1.491(5) . ?
C33 C34 1.502(5) . ?
C34 C39 1.390(5) . ?
C34 C35 1.396(5) . ?
C35 C36 1.402(5) . ?
C36 C37 1.396(6) . ?
C37 C38 1.350(6) . ?
C38 C39 1.386(5) . ?
C40 C45 1.390(5) . ?
C40 C41 1.392(5) . ?
C41 C42 1.378(5) . ?
C42 C43 1.386(5) . ?
C43 C44 1.372(5) . ?
C44 C45 1.389(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 C13 106.1(3) . . ?
C1 N1 C7 123.8(3) . . ?
C13 N1 C7 126.5(3) . . ?
C13 N2 C6 105.3(3) . . ?
C20 N3 C31 107.7(3) . . ?
C20 N3 C32 126.5(3) . . ?
C31 N3 C32 124.6(3) . . ?
C2 C1 N1 133.0(3) . . ?
C2 C1 C6 121.5(3) . . ?
N1 C1 C6 105.6(3) . . ?
C3 C2 C1 117.8(3) . . ?
C2 C3 C4 121.8(4) . . ?
C3 C4 C5 120.8(4) . . ?
C4 C5 C6 118.5(3) . . ?
N2 C6 C5 130.0(3) . . ?
N2 C6 C1 110.4(3) . . ?
C5 C6 C1 119.6(3) . . ?
C8 C7 C12 119.2(3) . . ?
C8 C7 N1 121.4(3) . . ?
C12 C7 N1 119.3(3) . . ?
C7 C8 C9 119.8(4) . . ?
C10 C9 C8 121.2(4) . . ?
C11 C10 C9 119.1(4) . . ?
C10 C11 C12 120.5(4) . . ?
C11 C12 C7 120.2(3) . . ?
N2 C13 N1 112.6(3) . . ?
N2 C13 C14 122.7(3) . . ?
N1 C13 C14 124.6(3) . . ?
C19 C14 C15 116.8(3) . . ?
C19 C14 C13 123.7(3) . . ?
C15 C14 C13 119.4(3) . . ?
C16 C15 C14 121.4(3) . . ?
C15 C16 C17 122.0(3) . . ?
C16 C17 C18 116.2(3) . . ?
C16 C17 C23 121.8(3) . . ?
C18 C17 C23 122.1(3) . . ?
C19 C18 C17 121.9(3) . . ?
C18 C19 C14 121.7(3) . . ?
N3 C20 C21 129.3(3) . . ?
N3 C20 C25 110.3(3) . . ?
C21 C20 C25 120.4(3) . . ?
C22 C21 C20 118.3(3) . . ?
C21 C22 C23 122.7(3) . . ?
C24 C23 C22 118.1(3) . . ?
C24 C23 C17 121.7(3) . . ?
C22 C23 C17 120.1(3) . . ?
C25 C24 C23 120.5(3) . . ?
C24 C25 C20 120.1(3) . . ?
C24 C25 C26 134.4(3) . . ?
C20 C25 C26 105.5(3) . . ?
C27 C26 C31 119.5(3) . . ?
C27 C26 C25 132.7(3) . . ?
C31 C26 C25 107.7(3) . . ?
C28 C27 C26 118.1(4) . . ?
C29 C28 C27 121.7(4) . . ?
C30 C29 C28 120.7(4) . . ?
C29 C30 C31 117.4(4) . . ?
C30 C31 C26 122.5(3) . . ?
C30 C31 N3 128.8(3) . . ?
C26 C31 N3 108.7(3) . . ?
C33 C32 N3 124.7(3) . . ?
C32 C33 C40 119.6(3) . . ?
C32 C33 C34 125.0(3) . . ?
C40 C33 C34 115.4(3) . . ?
C39 C34 C35 118.3(3) . . ?
C39 C34 C33 120.6(4) . . ?
C35 C34 C33 120.9(3) . . ?
C34 C35 C36 119.9(4) . . ?
C37 C36 C35 119.7(4) . . ?
C38 C37 C36 120.3(4) . . ?
C37 C38 C39 120.4(5) . . ?
C38 C39 C34 121.3(4) . . ?
C45 C40 C41 118.5(3) . . ?
C45 C40 C33 120.5(3) . . ?
C41 C40 C33 121.0(3) . . ?
C42 C41 C40 120.9(3) . . ?
C41 C42 C43 120.1(3) . . ?
C44 C43 C42 119.7(3) . . ?
C43 C44 C45 120.4(4) . . ?
C44 C45 C40 120.4(3) . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_ic21243_sq
_database_code_depnum_ccdc_archive 'CCDC 2153891'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung Liu'
;Instrumentation Center, National Taiwan University 
Taiwan
;
_audit_update_record             
;
2022-02-22 deposited with the CCDC.	2022-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H32 Cl N3'
_chemical_formula_weight         650.18

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                   9.1375(11)
_cell_length_b                   11.3158(13)
_cell_length_c                   18.3796(13)
_cell_angle_alpha                77.293(8)
_cell_angle_beta                 86.737(8)
_cell_angle_gamma                81.617(10)
_cell_volume                     1833.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5155
_cell_measurement_theta_min      3.3080
_cell_measurement_theta_max      31.8950

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40975
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_reflns_number            18358
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.120
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8411
_reflns_number_gt                5417
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0871P)²+0.4390P] 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         8411
_refine_ls_number_parameters     473
_refine_ls_number_restraints     372
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.2063
_refine_ls_wR_factor_gt          0.1694
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.06080(9) 0.58921(8) 0.35085(4) 0.0538(3) Uani 1 1 d . . . . .
N1 N 0.2974(2) 0.7525(2) 0.35085(10) 0.0278(5) Uani 1 1 d . . . . .
H1 H 0.221054 0.712906 0.364881 0.042 Uiso 1 1 calc R U . . .
N2 N 0.5072(2) 0.8234(2) 0.35415(10) 0.0228(4) Uani 1 1 d . . . . .
N3 N 0.4398(2) 0.2881(2) 0.91835(10) 0.0235(5) Uani 1 1 d . . . . .
C1 C 0.3211(3) 0.8225(2) 0.27998(12) 0.0245(5) Uani 1 1 d . . . . .
C2 C 0.2357(3) 0.8517(3) 0.21699(13) 0.0301(6) Uani 1 1 d . . . . .
H2A H 0.143405 0.822641 0.216413 0.036 Uiso 1 1 calc R U . . .
C3 C 0.2929(3) 0.9257(3) 0.15495(13) 0.0303(6) Uani 1 1 d . . . . .
H3A H 0.238622 0.948076 0.110280 0.036 Uiso 1 1 calc R U . . .
C4 C 0.4284(3) 0.9683(2) 0.15637(12) 0.0273(6) Uani 1 1 d . . . . .
H4A H 0.464276 1.017433 0.112086 0.033 Uiso 1 1 calc R U . . .
C5 C 0.5125(3) 0.9420(2) 0.21952(12) 0.0249(5) Uani 1 1 d . . . . .
H5A H 0.603598 0.972662 0.220618 0.030 Uiso 1 1 calc R U . . .
C6 C 0.4537(3) 0.8669(2) 0.28164(12) 0.0229(5) Uani 1 1 d . . . . .
C7 C 0.6338(4) 0.8596(4) 0.38026(18) 0.0303(11) Uani 0.652(5) 1 d G U P A 1
C8 C 0.7698(5) 0.8379(4) 0.34424(19) 0.0321(10) Uani 0.652(5) 1 d G U P A 1
H8A H 0.778231 0.795075 0.304813 0.039 Uiso 0.652(5) 1 calc R U P A 1
C9 C 0.8933(4) 0.8787(4) 0.36589(19) 0.0465(12) Uani 0.652(5) 1 d G U P A 1
H9A H 0.986293 0.863871 0.341271 0.056 Uiso 0.652(5) 1 calc R U P A 1
C10 C 0.8809(4) 0.9413(4) 0.42358(18) 0.0485(11) Uani 0.652(5) 1 d G U P A 1
H10A H 0.965408 0.969268 0.438378 0.058 Uiso 0.652(5) 1 calc R U P A 1
C11 C 0.7449(4) 0.9631(4) 0.45960(17) 0.0522(11) Uani 0.652(5) 1 d G U P A 1
H11A H 0.736461 1.005869 0.499028 0.063 Uiso 0.652(5) 1 calc R U P A 1
C12 C 0.6213(3) 0.9222(4) 0.43795(17) 0.0426(10) Uani 0.652(5) 1 d G U P A 1
H12A H 0.528397 0.937074 0.462571 0.051 Uiso 0.652(5) 1 calc R U P A 1
C7' C 0.6210(9) 0.8792(7) 0.3787(4) 0.0367(17) Uani 0.348(5) 1 d G U P A 2
C8' C 0.7696(10) 0.8446(7) 0.3627(5) 0.0391(15) Uani 0.348(5) 1 d G U P A 2
H8'A H 0.798184 0.776581 0.340130 0.047 Uiso 0.348(5) 1 calc R U P A 2
C9' C 0.8762(7) 0.9094(7) 0.3799(4) 0.0395(15) Uani 0.348(5) 1 d G U P A 2
H9'A H 0.977751 0.885740 0.368927 0.047 Uiso 0.348(5) 1 calc R U P A 2
C10' C 0.8344(7) 1.0089(7) 0.4130(4) 0.0456(16) Uani 0.348(5) 1 d G U P A 2
H10B H 0.907269 1.053171 0.424642 0.055 Uiso 0.348(5) 1 calc R U P A 2
C11' C 0.6858(8) 1.0435(7) 0.4289(4) 0.0493(16) Uani 0.348(5) 1 d G U P A 2
H11B H 0.657218 1.111444 0.451561 0.059 Uiso 0.348(5) 1 calc R U P A 2
C12' C 0.5792(7) 0.9786(7) 0.4118(4) 0.0432(15) Uani 0.348(5) 1 d G U P A 2
H12B H 0.477648 1.002287 0.422764 0.052 Uiso 0.348(5) 1 calc R U P A 2
C13 C 0.4089(3) 0.7548(2) 0.39432(12) 0.0239(5) Uani 1 1 d . . . . .
C14 C 0.4193(3) 0.6901(2) 0.47239(12) 0.0258(6) Uani 1 1 d . . . . .
C15 C 0.2881(3) 0.6705(3) 0.51374(12) 0.0295(6) Uani 1 1 d . . . . .
H15A H 0.194743 0.700922 0.491671 0.035 Uiso 1 1 calc R U . . .
C16 C 0.2959(3) 0.6060(3) 0.58726(13) 0.0306(6) Uani 1 1 d . . . . .
H16A H 0.206961 0.594357 0.615611 0.037 Uiso 1 1 calc R U . . .
C17 C 0.4313(3) 0.5579(2) 0.62050(12) 0.0245(5) Uani 1 1 d . . . . .
C18 C 0.5609(3) 0.5769(3) 0.57787(12) 0.0291(6) Uani 1 1 d . . . . .
H18A H 0.654150 0.544145 0.599421 0.035 Uiso 1 1 calc R U . . .
C19 C 0.5555(3) 0.6430(3) 0.50450(12) 0.0287(6) Uani 1 1 d . . . . .
H19A H 0.644547 0.655942 0.476435 0.034 Uiso 1 1 calc R U . . .
C20 C 0.4584(3) 0.3564(2) 0.84588(12) 0.0228(5) Uani 1 1 d . . . . .
C21 C 0.5780(3) 0.4152(2) 0.81471(12) 0.0255(5) Uani 1 1 d . . . . .
H21A H 0.663455 0.412171 0.842561 0.031 Uiso 1 1 calc R U . . .
C22 C 0.5665(3) 0.4786(2) 0.74108(12) 0.0267(6) Uani 1 1 d . . . . .
H22A H 0.647233 0.518095 0.717963 0.032 Uiso 1 1 calc R U . . .
C23 C 0.4394(3) 0.4865(2) 0.69920(12) 0.0243(5) Uani 1 1 d . . . . .
C24 C 0.3198(3) 0.4290(2) 0.73229(11) 0.0225(5) Uani 1 1 d . . . . .
H24A H 0.232960 0.434166 0.705027 0.027 Uiso 1 1 calc R U . . .
C25 C 0.3297(3) 0.3636(2) 0.80614(11) 0.0212(5) Uani 1 1 d . . . . .
C26 C 0.2272(3) 0.2961(2) 0.85600(12) 0.0215(5) Uani 1 1 d . . . . .
C27 C 0.0844(3) 0.2740(2) 0.84870(12) 0.0259(6) Uani 1 1 d . . . . .
H27A H 0.034823 0.304285 0.802889 0.031 Uiso 1 1 calc R U . . .
C28 C 0.0149(3) 0.2066(2) 0.90987(13) 0.0268(6) Uani 1 1 d . . . . .
H28A H -0.084147 0.192468 0.906354 0.032 Uiso 1 1 calc R U . . .
C29 C 0.0897(3) 0.1593(2) 0.97651(13) 0.0276(6) Uani 1 1 d . . . . .
H29A H 0.040989 0.111478 1.017102 0.033 Uiso 1 1 calc R U . . .
C30 C 0.2319(3) 0.1802(2) 0.98503(12) 0.0261(6) Uani 1 1 d . . . . .
H30A H 0.281735 0.147682 1.030575 0.031 Uiso 1 1 calc R U . . .
C31 C 0.3002(3) 0.2510(2) 0.92411(12) 0.0221(5) Uani 1 1 d . . . . .
C32 C 0.5461(3) 0.2645(2) 0.97386(12) 0.0235(5) Uani 1 1 d . . . . .
H32A H 0.644537 0.234925 0.960655 0.028 Uiso 1 1 calc R U . . .
C33 C 0.5204(3) 0.2802(2) 1.04409(12) 0.0228(5) Uani 1 1 d . . . . .
C34 C 0.6407(3) 0.2331(2) 1.09942(11) 0.0224(5) Uani 1 1 d . . . . .
C35 C 0.7376(3) 0.1273(2) 1.09700(12) 0.0262(6) Uani 1 1 d . . . . .
H35A H 0.727045 0.083025 1.059715 0.031 Uiso 1 1 calc R U . . .
C36 C 0.8497(3) 0.0851(3) 1.14819(13) 0.0290(6) Uani 1 1 d . . . . .
H36A H 0.915797 0.013114 1.145491 0.035 Uiso 1 1 calc R U . . .
C37 C 0.8645(3) 0.1486(3) 1.20310(14) 0.0340(6) Uani 1 1 d . . . . .
H37A H 0.940679 0.119803 1.238336 0.041 Uiso 1 1 calc R U . . .
C38 C 0.7694(3) 0.2529(3) 1.20677(14) 0.0358(7) Uani 1 1 d . . . . .
H38A H 0.780508 0.296249 1.244456 0.043 Uiso 1 1 calc R U . . .
C39 C 0.6569(3) 0.2958(3) 1.15573(13) 0.0294(6) Uani 1 1 d . . . . .
H39A H 0.590978 0.367614 1.159033 0.035 Uiso 1 1 calc R U . . .
C40 C 0.3785(3) 0.3435(2) 1.06784(12) 0.0244(5) Uani 1 1 d . . . . .
C41 C 0.3081(3) 0.2972(2) 1.13575(13) 0.0288(6) Uani 1 1 d . . . . .
H41A H 0.355557 0.227453 1.168976 0.035 Uiso 1 1 calc R U . . .
C42 C 0.1705(3) 0.3519(3) 1.15486(15) 0.0358(7) Uani 1 1 d . . . . .
H42A H 0.123030 0.317823 1.200390 0.043 Uiso 1 1 calc R U . . .
C43 C 0.1006(3) 0.4562(3) 1.10837(17) 0.0409(7) Uani 1 1 d . . . . .
H43A H 0.005192 0.492687 1.121435 0.049 Uiso 1 1 calc R U . . .
C44 C 0.1725(3) 0.5066(3) 1.04205(16) 0.0370(7) Uani 1 1 d . . . . .
H44A H 0.127581 0.579548 1.010563 0.044 Uiso 1 1 calc R U . . .
C45 C 0.3086(3) 0.4505(2) 1.02242(14) 0.0296(6) Uani 1 1 d . . . . .
H45A H 0.356001 0.485096 0.977017 0.035 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
N1 C13 1.336(3) . ?
N1 C1 1.391(3) . ?
N2 C13 1.352(3) . ?
N2 C6 1.405(3) . ?
N2 C7 1.423(3) . ?
N2 C7' 1.434(6) . ?
N3 C31 1.391(3) . ?
N3 C20 1.400(3) . ?
N3 C32 1.405(3) . ?
C1 C6 1.382(4) . ?
C1 C2 1.385(3) . ?
C2 C3 1.384(3) . ?
C3 C4 1.396(4) . ?
C4 C5 1.382(3) . ?
C5 C6 1.397(3) . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C8 C9 1.3900 . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C11 C12 1.3900 . ?
C7' C8' 1.3900 . ?
C7' C12' 1.3900 . ?
C8' C9' 1.3900 . ?
C9' C10' 1.3900 . ?
C10' C11' 1.3900 . ?
C11' C12' 1.3900 . ?
C13 C14 1.462(3) . ?
C14 C19 1.391(4) . ?
C14 C15 1.402(3) . ?
C15 C16 1.388(3) . ?
C16 C17 1.394(4) . ?
C17 C18 1.399(3) . ?
C17 C23 1.494(3) . ?
C18 C19 1.391(3) . ?
C20 C21 1.392(3) . ?
C20 C25 1.402(3) . ?
C21 C22 1.387(3) . ?
C22 C23 1.410(3) . ?
C23 C24 1.395(3) . ?
C24 C25 1.397(3) . ?
C25 C26 1.451(3) . ?
C26 C27 1.384(3) . ?
C26 C31 1.410(3) . ?
C27 C28 1.390(3) . ?
C28 C29 1.397(3) . ?
C29 C30 1.378(4) . ?
C30 C31 1.399(3) . ?
C32 C33 1.344(3) . ?
C33 C40 1.479(4) . ?
C33 C34 1.498(3) . ?
C34 C35 1.389(4) . ?
C34 C39 1.403(3) . ?
C35 C36 1.390(3) . ?
C36 C37 1.384(4) . ?
C37 C38 1.372(4) . ?
C38 C39 1.392(4) . ?
C40 C45 1.400(4) . ?
C40 C41 1.402(3) . ?
C41 C42 1.380(4) . ?
C42 C43 1.389(4) . ?
C43 C44 1.398(4) . ?
C44 C45 1.378(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
C13 N1 C1 109.3(2) . . ?
C13 N2 C6 107.82(19) . . ?
C13 N2 C7 127.8(2) . . ?
C6 N2 C7 124.0(2) . . ?
C13 N2 C7' 129.9(4) . . ?
C6 N2 C7' 119.7(4) . . ?
C31 N3 C20 107.86(19) . . ?
C31 N3 C32 127.78(18) . . ?
C20 N3 C32 124.4(2) . . ?
C6 C1 C2 122.2(2) . . ?
C6 C1 N1 106.6(2) . . ?
C2 C1 N1 131.2(2) . . ?
C3 C2 C1 116.0(2) . . ?
C2 C3 C4 121.6(2) . . ?
C5 C4 C3 122.7(2) . . ?
C4 C5 C6 115.0(2) . . ?
C1 C6 C5 122.4(2) . . ?
C1 C6 N2 107.11(19) . . ?
C5 C6 N2 130.5(2) . . ?
C8 C7 C12 120.0 . . ?
C8 C7 N2 118.9(3) . . ?
C12 C7 N2 121.0(3) . . ?
C7 C8 C9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C9 C10 C11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C11 C12 C7 120.0 . . ?
C8' C7' C12' 120.0 . . ?
C8' C7' N2 121.3(5) . . ?
C12' C7' N2 118.3(5) . . ?
C9' C8' C7' 120.0 . . ?
C10' C9' C8' 120.0 . . ?
C9' C10' C11' 120.0 . . ?
C12' C11' C10' 120.0 . . ?
C11' C12' C7' 120.0 . . ?
N1 C13 N2 109.18(19) . . ?
N1 C13 C14 123.6(2) . . ?
N2 C13 C14 127.2(2) . . ?
C19 C14 C15 120.1(2) . . ?
C19 C14 C13 121.3(2) . . ?
C15 C14 C13 118.5(2) . . ?
C16 C15 C14 119.3(2) . . ?
C15 C16 C17 121.5(2) . . ?
C16 C17 C18 118.2(2) . . ?
C16 C17 C23 121.4(2) . . ?
C18 C17 C23 120.3(2) . . ?
C19 C18 C17 121.2(2) . . ?
C18 C19 C14 119.7(2) . . ?
C21 C20 N3 128.8(2) . . ?
C21 C20 C25 122.1(2) . . ?
N3 C20 C25 109.0(2) . . ?
C22 C21 C20 116.8(2) . . ?
C21 C22 C23 122.5(2) . . ?
C24 C23 C22 119.5(2) . . ?
C24 C23 C17 120.1(2) . . ?
C22 C23 C17 120.5(2) . . ?
C23 C24 C25 118.9(2) . . ?
C24 C25 C20 120.1(2) . . ?
C24 C25 C26 132.6(2) . . ?
C20 C25 C26 107.34(19) . . ?
C27 C26 C31 120.5(2) . . ?
C27 C26 C25 133.5(2) . . ?
C31 C26 C25 106.0(2) . . ?
C26 C27 C28 118.5(2) . . ?
C27 C28 C29 120.5(2) . . ?
C30 C29 C28 121.9(2) . . ?
C29 C30 C31 117.5(2) . . ?
N3 C31 C30 129.3(2) . . ?
N3 C31 C26 109.82(19) . . ?
C30 C31 C26 120.9(2) . . ?
C33 C32 N3 125.5(2) . . ?
C32 C33 C40 122.1(2) . . ?
C32 C33 C34 118.5(2) . . ?
C40 C33 C34 119.4(2) . . ?
C35 C34 C39 118.4(2) . . ?
C35 C34 C33 121.6(2) . . ?
C39 C34 C33 120.0(2) . . ?
C34 C35 C36 121.1(2) . . ?
C37 C36 C35 119.7(3) . . ?
C38 C37 C36 120.2(2) . . ?
C37 C38 C39 120.5(3) . . ?
C38 C39 C34 120.1(3) . . ?
C45 C40 C41 117.8(2) . . ?
C45 C40 C33 121.0(2) . . ?
C41 C40 C33 121.2(2) . . ?
C42 C41 C40 120.7(3) . . ?
C41 C42 C43 120.8(3) . . ?
C42 C43 C44 119.1(3) . . ?
C45 C44 C43 119.9(3) . . ?
C44 C45 C40 121.5(2) . . ?

_refine_diff_density_max         0.608
_refine_diff_density_min         -0.830
_refine_diff_density_rms         0.066



