# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_ic19393
_database_code_depnum_ccdc_archive 'CCDC 2040255'
loop_
_audit_author_name
_audit_author_address
'Yi-Mei Huang'
;Department of Chemistry, National Taiwan University
Taiwan
;
_audit_update_record             
;
2020-10-23 deposited with the CCDC.	2020-12-28 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 H29 Cl2 N5'
_chemical_formula_weight         710.63

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

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

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

_cell_length_a                   13.9799(4)
_cell_length_b                   13.6973(3)
_cell_length_c                   19.2628(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.586(3)
_cell_angle_gamma                90
_cell_volume                     3535.10(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    10410
_cell_measurement_theta_min      2.9170
_cell_measurement_theta_max      29.3120

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             1472
_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    0.225
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90760
_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      150(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            37726
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.974
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7980
_reflns_number_gt                5931
_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       '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)+(0.0585P)²+3.0362P] 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         7980
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1441
_refine_ls_wR_factor_gt          0.1260
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002

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 0.46662(16) 0.65291(15) 0.48075(12) 0.0530(5) Uani 1 1 d . . . . .
N2 N 0.34020(12) 0.26629(12) 0.17772(9) 0.0295(4) Uani 1 1 d . . . . .
N3 N 0.29738(12) 0.18869(12) 0.26786(9) 0.0281(4) Uani 1 1 d . . . . .
N4 N 0.18383(12) 0.38191(12) 0.28756(9) 0.0287(4) Uani 1 1 d . . . . .
N5 N 0.53013(13) 0.35496(14) 0.28084(10) 0.0394(4) Uani 1 1 d . . . . .
C1 C 0.44082(16) 0.59511(16) 0.43652(13) 0.0388(5) Uani 1 1 d . . . . .
C2 C 0.41079(15) 0.51893(14) 0.38281(11) 0.0323(4) Uani 1 1 d . . . . .
C3 C 0.48204(16) 0.47644(15) 0.35510(12) 0.0350(5) Uani 1 1 d . . . . .
H3A H 0.548444 0.500743 0.368402 0.042 Uiso 1 1 calc R U . . .
C4 C 0.45591(15) 0.39870(15) 0.30814(11) 0.0314(4) Uani 1 1 d . . . . .
C5 C 0.35812(14) 0.36184(14) 0.28831(10) 0.0272(4) Uani 1 1 d . . . . .
C6 C 0.28532(14) 0.41092(14) 0.31219(11) 0.0280(4) Uani 1 1 d . . . . .
C7 C 0.31189(15) 0.48848(14) 0.36016(11) 0.0308(4) Uani 1 1 d . . . . .
H7A H 0.262863 0.520524 0.377395 0.037 Uiso 1 1 calc R U . . .
C8 C 0.33332(14) 0.27255(14) 0.24385(11) 0.0273(4) Uani 1 1 d . . . . .
C9 C 0.30669(14) 0.17293(14) 0.15520(10) 0.0278(4) Uani 1 1 d . . . . .
C10 C 0.29756(15) 0.12836(15) 0.08880(11) 0.0326(4) Uani 1 1 d . . . . .
H10A H 0.314622 0.161850 0.050809 0.039 Uiso 1 1 calc R U . . .
C11 C 0.26267(15) 0.03340(15) 0.08018(12) 0.0353(5) Uani 1 1 d . . . . .
H11A H 0.254805 0.001384 0.035141 0.042 Uiso 1 1 calc R U . . .
C12 C 0.23877(15) -0.01644(15) 0.13615(12) 0.0356(5) Uani 1 1 d . . . . .
H12A H 0.215861 -0.081945 0.128408 0.043 Uiso 1 1 calc R U . . .
C13 C 0.24744(15) 0.02666(15) 0.20250(11) 0.0331(4) Uani 1 1 d . . . . .
H13A H 0.232010 -0.007740 0.240763 0.040 Uiso 1 1 calc R U . . .
C14 C 0.27999(14) 0.12318(14) 0.21032(11) 0.0280(4) Uani 1 1 d . . . . .
C15 C 0.28552(15) 0.16876(14) 0.33800(11) 0.0289(4) Uani 1 1 d . . . . .
C16 C 0.19870(16) 0.12478(15) 0.34331(12) 0.0356(5) Uani 1 1 d . . . . .
H16A H 0.146400 0.109978 0.300886 0.043 Uiso 1 1 calc R U . . .
C17 C 0.18887(18) 0.10258(17) 0.41112(13) 0.0428(5) Uani 1 1 d . . . . .
H17A H 0.129769 0.071785 0.415098 0.051 Uiso 1 1 calc R U . . .
C18 C 0.26434(19) 0.12489(17) 0.47299(13) 0.0421(5) Uani 1 1 d . . . . .
H18A H 0.257315 0.108961 0.519289 0.051 Uiso 1 1 calc R U . . .
C19 C 0.34992(17) 0.17032(16) 0.46744(12) 0.0378(5) Uani 1 1 d . . . . .
H19A H 0.401222 0.187014 0.509972 0.045 Uiso 1 1 calc R U . . .
C20 C 0.36113(15) 0.19164(15) 0.39984(11) 0.0325(4) Uani 1 1 d . . . . .
H20A H 0.420554 0.221871 0.395981 0.039 Uiso 1 1 calc R U . . .
C21 C 0.12377(14) 0.38461(13) 0.21540(11) 0.0279(4) Uani 1 1 d . . . . .
C22 C 0.14957(16) 0.40411(15) 0.15249(11) 0.0330(4) Uani 1 1 d . . . . .
H22A H 0.216632 0.417811 0.153663 0.040 Uiso 1 1 calc R U . . .
C23 C 0.07373(17) 0.40288(16) 0.08769(12) 0.0383(5) Uani 1 1 d . . . . .
H23A H 0.089380 0.415951 0.043740 0.046 Uiso 1 1 calc R U . . .
C24 C -0.02487(17) 0.38292(16) 0.08555(12) 0.0397(5) Uani 1 1 d . . . . .
H24A H -0.075124 0.381917 0.040355 0.048 Uiso 1 1 calc R U . . .
C25 C -0.05005(16) 0.36457(15) 0.14869(12) 0.0362(5) Uani 1 1 d . . . . .
H25A H -0.117453 0.352093 0.147205 0.043 Uiso 1 1 calc R U . . .
C26 C 0.02443(14) 0.36459(14) 0.21444(11) 0.0294(4) Uani 1 1 d . . . . .
C27 C 0.02397(15) 0.34960(14) 0.28856(11) 0.0298(4) Uani 1 1 d . . . . .
C28 C -0.04965(16) 0.32464(16) 0.32093(12) 0.0366(5) Uani 1 1 d . . . . .
H28A H -0.116623 0.315082 0.292362 0.044 Uiso 1 1 calc R U . . .
C29 C -0.02397(17) 0.31393(17) 0.39522(13) 0.0416(5) Uani 1 1 d . . . . .
H29A H -0.073756 0.296506 0.417767 0.050 Uiso 1 1 calc R U . . .
C30 C 0.07407(17) 0.32835(17) 0.43767(12) 0.0399(5) Uani 1 1 d . . . . .
H30A H 0.089834 0.321095 0.488741 0.048 Uiso 1 1 calc R U . . .
C31 C 0.14884(16) 0.35305(16) 0.40670(11) 0.0344(5) Uani 1 1 d . . . . .
H31A H 0.215596 0.362933 0.435609 0.041 Uiso 1 1 calc R U . . .
C32 C 0.12278(14) 0.36282(14) 0.33216(11) 0.0285(4) Uani 1 1 d . . . . .
C33 C 0.54526(19) 0.3789(2) 0.21442(15) 0.0538(7) Uani 1 1 d . . . . .
C34 C 0.5003(2) 0.4519(3) 0.16614(15) 0.0680(9) Uani 1 1 d . . . . .
H34A H 0.448956 0.491846 0.174111 0.082 Uiso 1 1 calc R U . . .
C35 C 0.5343(3) 0.4635(3) 0.10569(18) 0.0990(16) Uani 1 1 d . . . . .
H35A H 0.505818 0.512989 0.071500 0.119 Uiso 1 1 calc R U . . .
C36 C 0.6092(4) 0.4041(5) 0.0939(2) 0.128(3) Uani 1 1 d . . . . .
H36A H 0.631028 0.414027 0.052008 0.153 Uiso 1 1 calc R U . . .
C37 C 0.6515(3) 0.3320(4) 0.1417(3) 0.1063(19) Uani 1 1 d . . . . .
H37A H 0.701639 0.291520 0.132317 0.128 Uiso 1 1 calc R U . . .
C38 C 0.6216(2) 0.3171(3) 0.20454(19) 0.0713(11) Uani 1 1 d . . . . .
C39 C 0.6532(2) 0.2554(2) 0.2672(2) 0.0650(9) Uani 1 1 d . . . . .
C40 C 0.7273(2) 0.1835(3) 0.2901(3) 0.0981(17) Uani 1 1 d . . . . .
H40A H 0.765111 0.162633 0.258995 0.118 Uiso 1 1 calc R U . . .
C41 C 0.7443(3) 0.1440(3) 0.3578(4) 0.1085(19) Uani 1 1 d . . . . .
H41A H 0.794057 0.095092 0.373147 0.130 Uiso 1 1 calc R U . . .
C42 C 0.6906(2) 0.1739(2) 0.4044(2) 0.0786(11) Uani 1 1 d . . . . .
H42A H 0.705472 0.146341 0.451577 0.094 Uiso 1 1 calc R U . . .
C43 C 0.61526(17) 0.24343(17) 0.38336(17) 0.0522(7) Uani 1 1 d . . . . .
H43A H 0.577708 0.263435 0.414924 0.063 Uiso 1 1 calc R U . . .
C44 C 0.59743(16) 0.28211(17) 0.31466(16) 0.0457(6) Uani 1 1 d . . . . .
Cl1 Cl 0.05613(5) 0.60876(4) 0.29395(4) 0.04919(17) Uani 1 1 d . . . . .
Cl2 Cl 0.14074(8) 0.64643(7) 0.44745(4) 0.0890(3) Uani 1 1 d . . . . .
C45 C 0.0324(3) 0.6111(2) 0.37813(18) 0.0700(9) Uani 1 1 d . . . . .
H45A H 0.010721 0.545549 0.389152 0.084 Uiso 1 1 calc R U . . .
H45B H -0.022335 0.657688 0.376546 0.084 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 1.143(3) . ?
N2 C8 1.307(2) . ?
N2 C9 1.388(2) . ?
N3 C8 1.385(2) . ?
N3 C14 1.392(2) . ?
N3 C15 1.434(2) . ?
N4 C32 1.398(2) . ?
N4 C21 1.404(2) . ?
N4 C6 1.418(2) . ?
N5 C33 1.394(3) . ?
N5 C44 1.398(3) . ?
N5 C4 1.423(3) . ?
C1 C2 1.445(3) . ?
C2 C7 1.390(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.377(3) . ?
C4 C5 1.404(3) . ?
C5 C6 1.402(3) . ?
C5 C8 1.477(3) . ?
C6 C7 1.387(3) . ?
C9 C10 1.390(3) . ?
C9 C14 1.399(3) . ?
C10 C11 1.382(3) . ?
C11 C12 1.395(3) . ?
C12 C13 1.381(3) . ?
C13 C14 1.392(3) . ?
C15 C16 1.385(3) . ?
C15 C20 1.384(3) . ?
C16 C17 1.386(3) . ?
C17 C18 1.382(3) . ?
C18 C19 1.380(3) . ?
C19 C20 1.386(3) . ?
C21 C22 1.385(3) . ?
C21 C26 1.410(3) . ?
C22 C23 1.388(3) . ?
C23 C24 1.394(3) . ?
C24 C25 1.382(3) . ?
C25 C26 1.391(3) . ?
C26 C27 1.444(3) . ?
C27 C28 1.390(3) . ?
C27 C32 1.408(3) . ?
C28 C29 1.380(3) . ?
C29 C30 1.395(3) . ?
C30 C31 1.385(3) . ?
C31 C32 1.384(3) . ?
C33 C34 1.387(5) . ?
C33 C38 1.417(4) . ?
C34 C35 1.386(4) . ?
C35 C36 1.395(7) . ?
C36 C37 1.365(8) . ?
C37 C38 1.405(5) . ?
C38 C39 1.436(5) . ?
C39 C40 1.406(5) . ?
C39 C44 1.408(3) . ?
C40 C41 1.367(6) . ?
C41 C42 1.387(6) . ?
C42 C43 1.392(4) . ?
C43 C44 1.381(4) . ?
Cl1 C45 1.746(3) . ?
Cl2 C45 1.777(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
C8 N2 C9 104.64(16) . . ?
C8 N3 C14 105.44(15) . . ?
C8 N3 C15 128.54(16) . . ?
C14 N3 C15 125.92(16) . . ?
C32 N4 C21 108.41(16) . . ?
C32 N4 C6 125.09(16) . . ?
C21 N4 C6 125.60(16) . . ?
C33 N5 C44 109.7(2) . . ?
C33 N5 C4 123.9(2) . . ?
C44 N5 C4 126.37(19) . . ?
N1 C1 C2 177.5(3) . . ?
C7 C2 C3 120.88(18) . . ?
C7 C2 C1 120.09(19) . . ?
C3 C2 C1 119.04(19) . . ?
C4 C3 C2 119.53(19) . . ?
C3 C4 C5 120.77(19) . . ?
C3 C4 N5 118.93(18) . . ?
C5 C4 N5 120.29(18) . . ?
C6 C5 C4 118.68(18) . . ?
C6 C5 C8 121.01(17) . . ?
C4 C5 C8 120.31(17) . . ?
C7 C6 C5 120.27(18) . . ?
C7 C6 N4 119.30(17) . . ?
C5 C6 N4 120.42(17) . . ?
C2 C7 C6 119.48(18) . . ?
N2 C8 N3 113.92(16) . . ?
N2 C8 C5 123.30(17) . . ?
N3 C8 C5 122.74(17) . . ?
C10 C9 N2 128.78(18) . . ?
C10 C9 C14 120.67(18) . . ?
N2 C9 C14 110.55(17) . . ?
C11 C10 C9 117.41(19) . . ?
C10 C11 C12 121.45(19) . . ?
C13 C12 C11 121.93(19) . . ?
C12 C13 C14 116.46(19) . . ?
N3 C14 C13 132.49(19) . . ?
N3 C14 C9 105.45(16) . . ?
C13 C14 C9 122.02(18) . . ?
C16 C15 C20 120.33(19) . . ?
C16 C15 N3 119.48(18) . . ?
C20 C15 N3 120.19(17) . . ?
C15 C16 C17 119.3(2) . . ?
C18 C17 C16 120.5(2) . . ?
C19 C18 C17 119.9(2) . . ?
C18 C19 C20 120.1(2) . . ?
C19 C20 C15 119.83(19) . . ?
C22 C21 N4 129.74(18) . . ?
C22 C21 C26 121.83(18) . . ?
N4 C21 C26 108.43(17) . . ?
C21 C22 C23 117.47(19) . . ?
C22 C23 C24 121.6(2) . . ?
C25 C24 C23 120.5(2) . . ?
C24 C25 C26 119.2(2) . . ?
C25 C26 C21 119.35(19) . . ?
C25 C26 C27 133.36(19) . . ?
C21 C26 C27 107.28(17) . . ?
C28 C27 C32 119.34(19) . . ?
C28 C27 C26 133.74(19) . . ?
C32 C27 C26 106.90(17) . . ?
C29 C28 C27 119.0(2) . . ?
C28 C29 C30 120.9(2) . . ?
C31 C30 C29 121.2(2) . . ?
C30 C31 C32 117.6(2) . . ?
C31 C32 N4 129.05(18) . . ?
C31 C32 C27 121.96(19) . . ?
N4 C32 C27 108.94(17) . . ?
C34 C33 N5 128.8(3) . . ?
C34 C33 C38 123.7(3) . . ?
N5 C33 C38 107.5(3) . . ?
C35 C34 C33 116.6(4) . . ?
C34 C35 C36 121.5(5) . . ?
C37 C36 C35 120.9(3) . . ?
C36 C37 C38 120.5(4) . . ?
C37 C38 C33 116.8(4) . . ?
C37 C38 C39 135.6(4) . . ?
C33 C38 C39 107.5(2) . . ?
C40 C39 C44 118.2(4) . . ?
C40 C39 C38 134.3(3) . . ?
C44 C39 C38 107.4(3) . . ?
C41 C40 C39 119.3(3) . . ?
C40 C41 C42 121.4(3) . . ?
C41 C42 C43 121.2(4) . . ?
C44 C43 C42 117.2(3) . . ?
C43 C44 N5 129.3(2) . . ?
C43 C44 C39 122.7(3) . . ?
N5 C44 C39 107.8(3) . . ?
Cl1 C45 Cl2 110.84(17) . . ?

_refine_diff_density_max         0.846
_refine_diff_density_min         -0.966
_refine_diff_density_rms         0.048

