# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_PI33PPCz
_database_code_depnum_ccdc_archive 'CCDC 1893407'
loop_
_audit_author_name
_audit_author_address
'Zhiqiang Li'
;Jilin University
China
;
_audit_update_record             
;
2019-01-25 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            PI33PPCz
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H29 N3'
_chemical_formula_weight         611.71

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

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

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

_cell_length_a                   12.5354(8)
_cell_length_b                   14.1497(9)
_cell_length_c                   35.992(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6383.9(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3528
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      21.11

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             2560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38493
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         1.980
_diffrn_reflns_theta_max         26.048
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6307
_reflns_number_gt                4496
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury 3.7'
_computing_publication_material  'Mercury 3.7'
_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)+(0.0309P)²+1.7017P] 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         6307
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1094
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
N46 N 0.48340(13) 0.12946(11) 0.40914(4) 0.0304(4) Uani 1 1 d . . . . .
N48 N 0.08433(13) 0.24023(11) 0.27743(4) 0.0310(4) Uani 1 1 d . . . . .
C3 C 0.18225(16) 0.28655(13) 0.26939(5) 0.0280(5) Uani 1 1 d . . . . .
C4 C 0.02156(15) 0.25668(13) 0.30896(6) 0.0295(5) Uani 1 1 d . . . . .
C5 C 0.51371(17) -0.02057(14) 0.44902(5) 0.0344(5) Uani 1 1 d . . . . .
N47 N 0.65412(13) 0.17582(11) 0.40583(4) 0.0340(4) Uani 1 1 d . . . . .
C7 C 0.25931(15) 0.29255(13) 0.29690(5) 0.0277(4) Uani 1 1 d . . . . .
H7 H 0.248027 0.261746 0.320020 0.033 Uiso 1 1 calc R U . . .
C8 C 0.35314(15) 0.34322(12) 0.29106(5) 0.0259(4) Uani 1 1 d . . . . .
C9 C 0.43408(15) 0.35046(13) 0.32103(5) 0.0266(4) Uani 1 1 d . . . . .
C10 C 0.29386(17) 0.37640(13) 0.22880(6) 0.0326(5) Uani 1 1 d . . . . .
H10 H 0.306872 0.403918 0.205159 0.039 Uiso 1 1 calc R U . . .
C11 C 0.36961(16) 0.38520(13) 0.25659(5) 0.0309(5) Uani 1 1 d . . . . .
H11 H 0.433082 0.420050 0.252087 0.037 Uiso 1 1 calc R U . . .
C12 C 0.54375(16) 0.06202(13) 0.42827(5) 0.0307(5) Uani 1 1 d . . . . .
C13 C -0.06354(16) 0.14677(13) 0.27315(6) 0.0315(5) Uani 1 1 d . . . . .
C14 C 0.37050(16) 0.12764(14) 0.40185(5) 0.0303(5) Uani 1 1 d . . . . .
C15 C 0.03757(17) 0.32138(14) 0.33749(6) 0.0365(5) Uani 1 1 d . . . . .
H15 H 0.098570 0.361202 0.337878 0.044 Uiso 1 1 calc R U . . .
C16 C -0.06939(16) 0.19897(13) 0.30760(6) 0.0316(5) Uani 1 1 d . . . . .
C17 C 0.73447(17) 0.04011(14) 0.44090(5) 0.0350(5) Uani 1 1 d . . . . .
C18 C 0.52943(15) 0.27838(13) 0.37267(5) 0.0287(5) Uani 1 1 d . . . . .
C19 C 0.49497(16) 0.43197(13) 0.32599(6) 0.0314(5) Uani 1 1 d . . . . .
H19 H 0.483603 0.484914 0.310248 0.038 Uiso 1 1 calc R U . . .
C20 C 0.58961(16) 0.36044(14) 0.37667(6) 0.0341(5) Uani 1 1 d . . . . .
H20 H 0.643068 0.364017 0.395331 0.041 Uiso 1 1 calc R U . . .
C21 C 0.84015(18) 0.07215(16) 0.43812(6) 0.0426(6) Uani 1 1 d . . . . .
H21 H 0.854884 0.130099 0.425818 0.051 Uiso 1 1 calc R U . . .
C22 C 0.55562(16) 0.19632(14) 0.39604(5) 0.0305(5) Uani 1 1 d . . . . .
C23 C 0.64726(17) 0.09221(14) 0.42528(5) 0.0324(5) Uani 1 1 d . . . . .
C24 C 0.59922(19) -0.07573(14) 0.46329(6) 0.0380(5) Uani 1 1 d . . . . .
C25 C 0.40767(18) -0.04766(15) 0.45694(6) 0.0403(5) Uani 1 1 d . . . . .
H25 H 0.350296 -0.009817 0.448226 0.048 Uiso 1 1 calc R U . . .
C26 C 0.19944(16) 0.32810(13) 0.23496(5) 0.0310(5) Uani 1 1 d . . . . .
H26 H 0.147230 0.323455 0.215912 0.037 Uiso 1 1 calc R U . . .
C27 C 0.06349(17) 0.13357(14) 0.22181(6) 0.0352(5) Uani 1 1 d . . . . .
H27 H 0.128766 0.150997 0.210281 0.042 Uiso 1 1 calc R U . . .
C28 C 0.03203(16) 0.17327(13) 0.25548(5) 0.0294(5) Uani 1 1 d . . . . .
C29 C 0.45227(15) 0.27415(13) 0.34472(5) 0.0273(4) Uani 1 1 d . . . . .
H29 H 0.411341 0.218139 0.341782 0.033 Uiso 1 1 calc R U . . .
C30 C -0.14399(17) 0.20460(14) 0.33634(6) 0.0368(5) Uani 1 1 d . . . . .
H30 H -0.205333 0.165183 0.336155 0.044 Uiso 1 1 calc R U . . .
C31 C 0.30474(18) 0.19663(15) 0.41598(6) 0.0388(5) Uani 1 1 d . . . . .
H31 H 0.333066 0.245289 0.431253 0.047 Uiso 1 1 calc R U . . .
C32 C 0.19667(19) 0.19453(17) 0.40772(6) 0.0494(6) Uani 1 1 d . . . . .
H32 H 0.150925 0.242439 0.417107 0.059 Uiso 1 1 calc R U . . .
C33 C 0.71038(18) -0.04536(15) 0.45921(5) 0.0379(5) Uani 1 1 d . . . . .
C34 C -0.03839(17) 0.32572(15) 0.36527(6) 0.0405(5) Uani 1 1 d . . . . .
H34 H -0.029128 0.369397 0.385058 0.049 Uiso 1 1 calc R U . . .
C35 C 0.57164(16) 0.43669(14) 0.35353(6) 0.0356(5) Uani 1 1 d . . . . .
H35 H 0.612311 0.492810 0.356561 0.043 Uiso 1 1 calc R U . . .
C36 C -0.12800(17) 0.26782(15) 0.36502(6) 0.0397(5) Uani 1 1 d . . . . .
H36 H -0.178438 0.271788 0.384655 0.048 Uiso 1 1 calc R U . . .
C37 C -0.12985(18) 0.08093(14) 0.25598(6) 0.0406(6) Uani 1 1 d . . . . .
H37 H -0.195138 0.062867 0.267346 0.049 Uiso 1 1 calc R U . . .
C38 C 0.32931(18) 0.05640(15) 0.38005(6) 0.0396(5) Uani 1 1 d . . . . .
H38 H 0.375112 0.008921 0.370357 0.048 Uiso 1 1 calc R U . . .
C39 C 0.3864(2) -0.12775(16) 0.47704(6) 0.0480(6) Uani 1 1 d . . . . .
H39 H 0.314661 -0.144682 0.482364 0.058 Uiso 1 1 calc R U . . .
C40 C 0.92228(19) 0.02061(17) 0.45301(7) 0.0512(6) Uani 1 1 d . . . . .
H40 H 0.993775 0.042251 0.450929 0.061 Uiso 1 1 calc R U . . .
C41 C 0.5728(2) -0.15853(16) 0.48286(6) 0.0516(7) Uani 1 1 d . . . . .
H41 H 0.628635 -0.198029 0.491685 0.062 Uiso 1 1 calc R U . . .
C42 C -0.00385(19) 0.06788(14) 0.20581(6) 0.0416(6) Uani 1 1 d . . . . .
H42 H 0.015861 0.039434 0.182904 0.050 Uiso 1 1 calc R U . . .
C43 C 0.8996(2) -0.06373(18) 0.47119(7) 0.0570(7) Uani 1 1 d . . . . .
H43 H 0.956241 -0.099614 0.481634 0.068 Uiso 1 1 calc R U . . .
C44 C -0.10027(19) 0.04225(14) 0.22250(6) 0.0442(6) Uani 1 1 d . . . . .
H44 H -0.145680 -0.002203 0.210617 0.053 Uiso 1 1 calc R U . . .
C45 C 0.4692(2) -0.18400(17) 0.48957(7) 0.0576(7) Uani 1 1 d . . . . .
H45 H 0.454190 -0.240430 0.502878 0.069 Uiso 1 1 calc R U . . .
C46 C 0.7973(2) -0.09574(16) 0.47424(6) 0.0510(6) Uani 1 1 d . . . . .
H46 H 0.784248 -0.153574 0.486855 0.061 Uiso 1 1 calc R U . . .
C47 C 0.15542(19) 0.12329(18) 0.38596(7) 0.0514(6) Uani 1 1 d . . . . .
H47 H 0.081350 0.121989 0.380402 0.062 Uiso 1 1 calc R U . . .
C48 C 0.22167(19) 0.05401(17) 0.37230(7) 0.0512(6) Uani 1 1 d . . . . .
H48 H 0.193189 0.004464 0.357499 0.061 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
N46 C22 1.392(2) . ?
N46 C12 1.399(2) . ?
N46 C14 1.440(2) . ?
N48 C28 1.397(2) . ?
N48 C4 1.400(2) . ?
N48 C3 1.421(2) . ?
C3 C7 1.386(3) . ?
C3 C26 1.388(3) . ?
C4 C15 1.390(3) . ?
C4 C16 1.403(3) . ?
C5 C25 1.412(3) . ?
C5 C24 1.422(3) . ?
C5 C12 1.437(3) . ?
N47 C22 1.316(2) . ?
N47 C23 1.377(2) . ?
C7 C8 1.393(3) . ?
C8 C11 1.391(3) . ?
C8 C9 1.484(3) . ?
C9 C29 1.394(3) . ?
C9 C19 1.394(3) . ?
C10 C11 1.385(3) . ?
C10 C26 1.385(3) . ?
C12 C23 1.370(3) . ?
C13 C37 1.393(3) . ?
C13 C28 1.407(3) . ?
C13 C16 1.445(3) . ?
C14 C31 1.375(3) . ?
C14 C38 1.378(3) . ?
C15 C34 1.382(3) . ?
C16 C30 1.397(3) . ?
C17 C21 1.404(3) . ?
C17 C33 1.410(3) . ?
C17 C23 1.433(3) . ?
C18 C20 1.392(3) . ?
C18 C29 1.397(3) . ?
C18 C22 1.471(3) . ?
C19 C35 1.382(3) . ?
C20 C35 1.382(3) . ?
C21 C40 1.371(3) . ?
C24 C41 1.406(3) . ?
C24 C33 1.466(3) . ?
C25 C39 1.371(3) . ?
C27 C42 1.381(3) . ?
C27 C28 1.393(3) . ?
C30 C36 1.380(3) . ?
C31 C32 1.387(3) . ?
C32 C47 1.377(3) . ?
C33 C46 1.410(3) . ?
C34 C36 1.390(3) . ?
C37 C44 1.375(3) . ?
C38 C48 1.378(3) . ?
C39 C45 1.384(3) . ?
C40 C43 1.390(3) . ?
C41 C45 1.369(3) . ?
C42 C44 1.398(3) . ?
C43 C46 1.365(3) . ?
C47 C48 1.376(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 N46 C12 106.18(16) . . ?
C22 N46 C14 126.15(16) . . ?
C12 N46 C14 127.52(16) . . ?
C28 N48 C4 107.90(16) . . ?
C28 N48 C3 127.07(17) . . ?
C4 N48 C3 125.01(16) . . ?
C7 C3 C26 120.24(18) . . ?
C7 C3 N48 118.99(17) . . ?
C26 C3 N48 120.74(18) . . ?
C15 C4 N48 128.82(18) . . ?
C15 C4 C16 121.74(19) . . ?
N48 C4 C16 109.37(17) . . ?
C25 C5 C24 119.18(19) . . ?
C25 C5 C12 124.9(2) . . ?
C24 C5 C12 115.89(19) . . ?
C22 N47 C23 105.48(17) . . ?
C3 C7 C8 120.81(17) . . ?
C11 C8 C7 118.65(18) . . ?
C11 C8 C9 121.15(17) . . ?
C7 C8 C9 120.20(17) . . ?
C29 C9 C19 118.22(18) . . ?
C29 C9 C8 120.16(17) . . ?
C19 C9 C8 121.61(17) . . ?
C11 C10 C26 121.01(19) . . ?
C10 C11 C8 120.27(19) . . ?
C23 C12 N46 105.12(17) . . ?
C23 C12 C5 122.84(19) . . ?
N46 C12 C5 131.98(19) . . ?
C37 C13 C28 119.0(2) . . ?
C37 C13 C16 133.8(2) . . ?
C28 C13 C16 107.15(17) . . ?
C31 C14 C38 120.4(2) . . ?
C31 C14 N46 120.61(18) . . ?
C38 C14 N46 119.03(18) . . ?
C34 C15 C4 117.66(19) . . ?
C30 C16 C4 119.02(19) . . ?
C30 C16 C13 134.32(19) . . ?
C4 C16 C13 106.62(18) . . ?
C21 C17 C33 120.8(2) . . ?
C21 C17 C23 121.72(19) . . ?
C33 C17 C23 117.45(19) . . ?
C20 C18 C29 119.04(18) . . ?
C20 C18 C22 118.58(18) . . ?
C29 C18 C22 122.18(17) . . ?
C35 C19 C9 120.81(18) . . ?
C35 C20 C18 120.04(19) . . ?
C40 C21 C17 120.6(2) . . ?
N47 C22 N46 111.69(17) . . ?
N47 C22 C18 122.44(18) . . ?
N46 C22 C18 125.82(18) . . ?
C12 C23 N47 111.51(18) . . ?
C12 C23 C17 122.08(18) . . ?
N47 C23 C17 126.40(19) . . ?
C41 C24 C5 117.4(2) . . ?
C41 C24 C33 121.2(2) . . ?
C5 C24 C33 121.30(18) . . ?
C39 C25 C5 120.9(2) . . ?
C10 C26 C3 118.97(19) . . ?
C42 C27 C28 117.5(2) . . ?
C27 C28 N48 129.26(19) . . ?
C27 C28 C13 121.79(18) . . ?
N48 C28 C13 108.94(17) . . ?
C9 C29 C18 121.35(17) . . ?
C36 C30 C16 119.6(2) . . ?
C14 C31 C32 119.4(2) . . ?
C47 C32 C31 120.3(2) . . ?
C46 C33 C17 116.6(2) . . ?
C46 C33 C24 123.2(2) . . ?
C17 C33 C24 120.14(19) . . ?
C15 C34 C36 121.7(2) . . ?
C20 C35 C19 120.54(19) . . ?
C30 C36 C34 120.3(2) . . ?
C44 C37 C13 119.6(2) . . ?
C14 C38 C48 120.0(2) . . ?
C25 C39 C45 120.1(2) . . ?
C21 C40 C43 119.2(2) . . ?
C45 C41 C24 122.1(2) . . ?
C27 C42 C44 121.6(2) . . ?
C46 C43 C40 121.0(2) . . ?
C37 C44 C42 120.5(2) . . ?
C41 C45 C39 120.2(2) . . ?
C43 C46 C33 121.8(2) . . ?
C48 C47 C32 119.9(2) . . ?
C47 C48 C38 120.1(2) . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.037

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_PI22PPCz
_database_code_depnum_ccdc_archive 'CCDC 1893408'
loop_
_audit_author_name
_audit_author_address
'Zhiqiang Li'
;Jilin University
China
;
_audit_update_record             
;
2019-07-27 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            PI22PPCz
_chemical_melting_point          ?
_chemical_formula_moiety         C45H29N3
_chemical_formula_sum            'C45 H29 N3'
_chemical_formula_weight         611.71

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

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

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

_cell_length_a                   10.052(2)
_cell_length_b                   14.186(3)
_cell_length_c                   21.411(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.84(3)
_cell_angle_gamma                90
_cell_volume                     3051.6(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    6815
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      27.58

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.330
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26267
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.026
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             6811
_reflns_number_gt                3472
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury 4.1'
_computing_publication_material  'Mercury 4.1'
_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)+(0.0629P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6811
_refine_ls_number_parameters     549
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.1627
_refine_ls_wR_factor_gt          0.1363
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
C4 C 0.1033(3) 0.34896(16) 0.03561(11) 0.0359(6) Uani 1 1 d . . . . .
C5 C 0.3005(3) 0.38446(15) 0.22755(11) 0.0362(6) Uani 1 1 d . . . . .
C6 C 0.0747(3) 0.21571(16) -0.06078(11) 0.0391(6) Uani 1 1 d . . . . .
C7 C 0.0809(3) 0.45723(15) 0.12941(11) 0.0357(6) Uani 1 1 d . . . . .
C8 C 0.2141(3) 0.31420(16) 0.00712(11) 0.0363(6) Uani 1 1 d . . . . .
C9 C -0.0300(3) 0.32710(16) 0.01527(11) 0.0399(6) Uani 1 1 d . . . . .
C10 C 0.5107(3) 0.15301(17) 0.12333(12) 0.0463(7) Uani 1 1 d . . . . .
C11 C -0.0418(3) 0.25629(17) -0.03190(11) 0.0403(6) Uani 1 1 d . . . . .
C12 C 0.2912(3) 0.39950(15) 0.08219(11) 0.0361(6) Uani 1 1 d . . . . .
C13 C 0.2035(3) 0.24596(16) -0.04251(11) 0.0373(6) Uani 1 1 d . . . . .
C14 C 0.2003(3) 0.23724(18) 0.25878(12) 0.0460(7) Uani 1 1 d . . . . .
C15 C 0.3884(3) 0.44564(14) 0.18989(11) 0.0354(6) Uani 1 1 d . . . . .
C16 C 0.2827(3) 0.28725(15) 0.21927(11) 0.0366(6) Uani 1 1 d . . . . .
C17 C 0.2354(3) 0.42697(18) 0.27741(12) 0.0438(6) Uani 1 1 d . . . . .
C18 C 0.2856(3) 0.17003(15) 0.13220(12) 0.0402(6) Uani 1 1 d . . . . .
C19 C 0.4866(3) 0.22373(16) 0.16770(12) 0.0410(6) Uani 1 1 d . . . . .
C20 C 0.0652(3) 0.14573(19) -0.10806(13) 0.0494(7) Uani 1 1 d . . . . .
C21 C 0.3835(3) 0.11927(16) 0.10076(12) 0.0447(7) Uani 1 1 d . . . . .
C22 C -0.0054(3) 0.41003(18) 0.16810(12) 0.0441(7) Uani 1 1 d . . . . .
C23 C 0.1535(3) 0.3767(2) 0.31560(12) 0.0511(7) Uani 1 1 d . . . . .
C24 C 0.3158(3) 0.20850(18) -0.07034(13) 0.0456(7) Uani 1 1 d . . . . .
C25 C 0.0964(3) 0.55357(17) 0.13341(13) 0.0448(7) Uani 1 1 d . . . . .
C26 C 0.3852(2) 0.45090(15) 0.12430(11) 0.0356(6) Uani 1 1 d . . . . .
C27 C 0.4807(3) 0.50148(16) 0.22311(13) 0.0418(6) Uani 1 1 d . . . . .
C28 C -0.0786(3) 0.4608(2) 0.20993(13) 0.0504(7) Uani 1 1 d . . . . .
C29 C -0.1455(3) 0.3701(2) 0.03715(13) 0.0509(7) Uani 1 1 d . . . . .
C30 C 0.5706(3) 0.55759(18) 0.19328(15) 0.0516(7) Uani 1 1 d . . . . .
C31 C 0.4781(3) 0.50800(18) 0.09494(13) 0.0454(7) Uani 1 1 d . . . . .
C32 C -0.2699(3) 0.3407(2) 0.01751(15) 0.0599(8) Uani 1 1 d . . . . .
C33 C 0.1152(4) 0.0850(2) 0.07817(15) 0.0576(8) Uani 1 1 d . . . . .
C34 C -0.1712(3) 0.2284(2) -0.05082(14) 0.0516(7) Uani 1 1 d . . . . .
C35 C 0.1766(3) 0.1095(2) -0.13465(14) 0.0571(8) Uani 1 1 d . . . . .
C36 C -0.0631(3) 0.5574(2) 0.21436(15) 0.0559(8) Uani 1 1 d . . . . .
C37 C 0.1348(3) 0.2814(2) 0.30590(13) 0.0525(7) Uani 1 1 d . . . . .
C38 C 0.1506(3) 0.15392(18) 0.12139(14) 0.0491(7) Uani 1 1 d . . . . .
C39 C 0.3023(3) 0.1406(2) -0.11596(14) 0.0552(8) Uani 1 1 d . . . . .
C40 C 0.7178(4) 0.2388(2) 0.18996(17) 0.0613(9) Uani 1 1 d . . . . .
C41 C 0.0243(3) 0.60306(19) 0.17650(14) 0.0530(8) Uani 1 1 d . . . . .
C42 C -0.2823(3) 0.2678(2) -0.02623(16) 0.0602(8) Uani 1 1 d . . . . .
C43 C 0.2093(4) 0.0334(2) 0.04707(15) 0.0626(9) Uani 1 1 d . . . . .
C44 C 0.5890(3) 0.26650(18) 0.20144(14) 0.0486(7) Uani 1 1 d . . . . .
C45 C 0.3425(4) 0.05020(19) 0.05750(13) 0.0583(9) Uani 1 1 d . . . . .
C46 C 0.6413(4) 0.1268(2) 0.11215(16) 0.0611(9) Uani 1 1 d . . . . .
C47 C 0.5716(3) 0.55939(19) 0.12868(15) 0.0527(8) Uani 1 1 d . . . . .
C48 C 0.7437(4) 0.1697(2) 0.14566(18) 0.0690(10) Uani 1 1 d . . . . .
N1 N 0.1544(2) 0.40413(13) 0.08503(9) 0.0364(5) Uani 1 1 d . . . . .
N2 N 0.3310(2) 0.34680(13) 0.03532(9) 0.0391(5) Uani 1 1 d . . . . .
N3 N 0.3494(2) 0.23549(12) 0.17224(9) 0.0393(5) Uani 1 1 d . . . . .
H1 H 0.483(3) 0.4993(16) 0.2706(12) 0.046(7) Uiso 1 1 d . . . . .
H2 H 0.639(3) 0.5946(16) 0.2190(12) 0.047(7) Uiso 1 1 d . . . . .
H3 H 0.196(3) 0.1685(19) 0.2519(13) 0.064(9) Uiso 1 1 d . . . . .
H4 H 0.475(3) 0.5139(18) 0.0505(13) 0.055(8) Uiso 1 1 d . . . . .
H5 H -0.140(3) 0.4237(19) 0.0649(13) 0.061(8) Uiso 1 1 d . . . . .
H6 H 0.183(3) -0.014(2) 0.0162(14) 0.070(9) Uiso 1 1 d . . . . .
H7 H 0.408(3) 0.2287(17) -0.0551(12) 0.053(8) Uiso 1 1 d . . . . .
H8 H -0.117(3) 0.5928(19) 0.2434(15) 0.074(9) Uiso 1 1 d . . . . .
H9 H 0.248(3) 0.4990(19) 0.2840(12) 0.059(8) Uiso 1 1 d . . . . .
H10 H -0.021(3) 0.1223(18) -0.1216(13) 0.056(8) Uiso 1 1 d . . . . .
H11 H -0.185(3) 0.1786(18) -0.0843(13) 0.061(8) Uiso 1 1 d . . . . .
H12 H 0.082(3) 0.191(2) 0.1445(15) 0.079(10) Uiso 1 1 d . . . . .
H13 H 0.837(4) 0.153(2) 0.1378(15) 0.088(11) Uiso 1 1 d . . . . .
H14 H 0.570(3) 0.3125(17) 0.2331(12) 0.051(8) Uiso 1 1 d . . . . .
H15 H 0.033(3) 0.673(2) 0.1783(13) 0.067(9) Uiso 1 1 d . . . . .
H16 H -0.013(3) 0.3399(18) 0.1639(12) 0.052(8) Uiso 1 1 d . . . . .
H17 H 0.025(3) 0.0717(17) 0.0701(12) 0.046(8) Uiso 1 1 d . . . . .
H18 H -0.143(3) 0.4297(18) 0.2368(14) 0.063(8) Uiso 1 1 d . . . . .
H19 H 0.164(3) 0.059(2) -0.1717(15) 0.081(10) Uiso 1 1 d . . . . .
H20 H 0.162(3) 0.5818(17) 0.1048(12) 0.052(8) Uiso 1 1 d . . . . .
H21 H 0.634(3) 0.5985(18) 0.1077(13) 0.059(8) Uiso 1 1 d . . . . .
H22 H 0.384(4) 0.115(2) -0.1361(16) 0.094(11) Uiso 1 1 d . . . . .
H23 H 0.791(3) 0.265(2) 0.2141(14) 0.070(10) Uiso 1 1 d . . . . .
H24 H 0.411(3) 0.015(2) 0.0371(14) 0.073(10) Uiso 1 1 d . . . . .
H25 H -0.350(4) 0.366(2) 0.0327(15) 0.086(11) Uiso 1 1 d . . . . .
H26 H 0.078(3) 0.244(2) 0.3326(14) 0.073(9) Uiso 1 1 d . . . . .
H27 H 0.652(3) 0.079(2) 0.0814(15) 0.072(9) Uiso 1 1 d . . . . .
H28 H 0.108(3) 0.4127(18) 0.3502(13) 0.058(8) Uiso 1 1 d . . . . .
H29 H -0.363(3) 0.248(2) -0.0388(15) 0.074(10) 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
C4 C8 1.378(3) . ?
C4 N1 1.400(3) . ?
C4 C9 1.430(4) . ?
C5 C16 1.401(3) . ?
C5 C17 1.406(3) . ?
C5 C15 1.493(3) . ?
C6 C13 1.408(4) . ?
C6 C20 1.419(3) . ?
C6 C11 1.460(3) . ?
C7 C25 1.378(3) . ?
C7 C22 1.390(3) . ?
C7 N1 1.436(3) . ?
C8 N2 1.384(3) . ?
C8 C13 1.439(3) . ?
C9 C29 1.405(4) . ?
C9 C11 1.427(3) . ?
C10 C46 1.393(4) . ?
C10 C19 1.408(3) . ?
C10 C21 1.435(4) . ?
C11 C34 1.407(4) . ?
C12 N2 1.324(3) . ?
C12 N1 1.380(3) . ?
C12 C26 1.478(3) . ?
C13 C24 1.398(3) . ?
C14 C37 1.374(4) . ?
C14 C16 1.396(3) . ?
C15 C27 1.397(3) . ?
C15 C26 1.406(3) . ?
C16 N3 1.431(3) . ?
C17 C23 1.378(4) . ?
C18 C38 1.389(4) . ?
C18 N3 1.405(3) . ?
C18 C21 1.407(3) . ?
C19 C44 1.380(4) . ?
C19 N3 1.395(3) . ?
C20 C35 1.373(4) . ?
C21 C45 1.401(4) . ?
C22 C28 1.381(3) . ?
C23 C37 1.379(4) . ?
C24 C39 1.375(4) . ?
C25 C41 1.383(4) . ?
C26 C31 1.400(3) . ?
C27 C30 1.377(4) . ?
C28 C36 1.381(4) . ?
C29 C32 1.372(4) . ?
C30 C47 1.384(4) . ?
C31 C47 1.376(4) . ?
C32 C42 1.398(4) . ?
C33 C43 1.384(5) . ?
C33 C38 1.385(4) . ?
C34 C42 1.369(4) . ?
C35 C39 1.385(4) . ?
C36 C41 1.376(4) . ?
C40 C44 1.382(4) . ?
C40 C48 1.395(5) . ?
C43 C45 1.371(5) . ?
C46 C48 1.377(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
C8 C4 N1 104.6(2) . . ?
C8 C4 C9 123.4(2) . . ?
N1 C4 C9 131.9(2) . . ?
C16 C5 C17 117.2(2) . . ?
C16 C5 C15 125.4(2) . . ?
C17 C5 C15 117.3(2) . . ?
C13 C6 C20 116.9(2) . . ?
C13 C6 C11 120.4(2) . . ?
C20 C6 C11 122.8(2) . . ?
C25 C7 C22 120.8(2) . . ?
C25 C7 N1 120.1(2) . . ?
C22 C7 N1 119.1(2) . . ?
C4 C8 N2 112.0(2) . . ?
C4 C8 C13 121.7(2) . . ?
N2 C8 C13 126.1(2) . . ?
C29 C9 C11 119.4(3) . . ?
C29 C9 C4 125.5(2) . . ?
C11 C9 C4 115.1(2) . . ?
C46 C10 C19 119.3(3) . . ?
C46 C10 C21 133.5(3) . . ?
C19 C10 C21 107.1(2) . . ?
C34 C11 C9 117.2(2) . . ?
C34 C11 C6 120.9(2) . . ?
C9 C11 C6 121.8(2) . . ?
N2 C12 N1 112.7(2) . . ?
N2 C12 C26 122.5(2) . . ?
N1 C12 C26 124.6(2) . . ?
C24 C13 C6 120.9(2) . . ?
C24 C13 C8 121.9(2) . . ?
C6 C13 C8 117.1(2) . . ?
C37 C14 C16 121.4(2) . . ?
C27 C15 C26 118.1(2) . . ?
C27 C15 C5 116.7(2) . . ?
C26 C15 C5 125.1(2) . . ?
C14 C16 C5 120.0(2) . . ?
C14 C16 N3 117.8(2) . . ?
C5 C16 N3 122.2(2) . . ?
C23 C17 C5 122.0(2) . . ?
C38 C18 N3 129.4(2) . . ?
C38 C18 C21 122.0(2) . . ?
N3 C18 C21 108.5(2) . . ?
C44 C19 N3 129.3(2) . . ?
C44 C19 C10 121.7(3) . . ?
N3 C19 C10 108.9(2) . . ?
C35 C20 C6 121.4(3) . . ?
C45 C21 C18 118.6(3) . . ?
C45 C21 C10 134.1(3) . . ?
C18 C21 C10 107.3(2) . . ?
C28 C22 C7 119.4(2) . . ?
C17 C23 C37 119.9(2) . . ?
C39 C24 C13 120.4(3) . . ?
C7 C25 C41 119.0(3) . . ?
C31 C26 C15 119.0(2) . . ?
C31 C26 C12 115.7(2) . . ?
C15 C26 C12 125.2(2) . . ?
C30 C27 C15 121.8(3) . . ?
C22 C28 C36 120.1(3) . . ?
C32 C29 C9 121.4(3) . . ?
C27 C30 C47 120.0(3) . . ?
C47 C31 C26 121.6(3) . . ?
C29 C32 C42 119.4(3) . . ?
C43 C33 C38 122.0(3) . . ?
C42 C34 C11 122.2(3) . . ?
C20 C35 C39 120.7(3) . . ?
C41 C36 C28 120.0(3) . . ?
C14 C37 C23 119.4(3) . . ?
C33 C38 C18 117.2(3) . . ?
C24 C39 C35 119.7(3) . . ?
C44 C40 C48 121.2(4) . . ?
C36 C41 C25 120.8(3) . . ?
C34 C42 C32 120.2(3) . . ?
C45 C43 C33 120.6(3) . . ?
C19 C44 C40 118.0(3) . . ?
C43 C45 C21 119.6(3) . . ?
C48 C46 C10 119.1(3) . . ?
C31 C47 C30 119.3(3) . . ?
C46 C48 C40 120.8(3) . . ?
C12 N1 C4 106.35(19) . . ?
C12 N1 C7 126.1(2) . . ?
C4 N1 C7 127.6(2) . . ?
C12 N2 C8 104.2(2) . . ?
C19 N3 C18 108.1(2) . . ?
C19 N3 C16 126.7(2) . . ?
C18 N3 C16 123.6(2) . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049


_exptl_crystal_recrystallization_method Sublimation
