# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2027073'
loop_
_audit_author_name
_audit_author_address
'Zhiyong Ma'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2020-09-03 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_audit_creation_date             2020-01-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H18 N4'
_chemical_formula_sum            'C30 H18 N4'
_chemical_formula_weight         434.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

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

_cell_length_a                   5.1918(3)
_cell_length_b                   12.6035(7)
_cell_length_c                   17.9678(10)
_cell_angle_alpha                105.516(2)
_cell_angle_beta                 91.670(2)
_cell_angle_gamma                100.816(2)
_cell_volume                     1108.83(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4719
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.40
_cell_measurement_theta_min      3.28
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             452
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24324
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.675
_diffrn_reflns_theta_min         3.281
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2757
_reflns_number_total             5622
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5622
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1464
_refine_ls_R_factor_gt           0.0581
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0601P)²+0.2394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1637
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C14(H14), C8(H8), C29(H29), C20(H20), C7(H7), C28(H28), C26(H26),
 C23(H23), C5(H5), C6(H6), C21(H21), C11(H11), C27(H27), C22(H22), C2(H2),
 C12(H12), C1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.8703(4) 0.66256(14) 0.20995(10) 0.0443(5) Uani 1 1 d . . . . .
N1 N 0.7111(4) 0.28231(15) 0.24507(10) 0.0452(5) Uani 1 1 d . . . . .
N4 N 1.1562(4) 0.41577(17) 0.12594(11) 0.0531(5) Uani 1 1 d . . . . .
N2 N 0.4243(4) 0.52638(18) 0.32164(12) 0.0616(6) Uani 1 1 d . . . . .
C15 C 0.7935(4) 0.47563(18) 0.23308(11) 0.0385(5) Uani 1 1 d . . . . .
C17 C 0.9264(4) 0.55353(17) 0.19747(12) 0.0396(5) Uani 1 1 d . . . . .
C13 C 0.8492(4) 0.36763(18) 0.21475(12) 0.0400(5) Uani 1 1 d . . . . .
C30 C 0.7219(4) 0.69254(18) 0.15477(13) 0.0440(5) Uani 1 1 d . . . . .
C19 C 0.8640(4) 0.73847(18) 0.28281(12) 0.0457(5) Uani 1 1 d . . . . .
C16 C 0.5897(4) 0.50432(18) 0.28325(13) 0.0442(5) Uani 1 1 d . . . . .
C9 C 0.5094(4) 0.19503(18) 0.20051(13) 0.0440(5) Uani 1 1 d . . . . .
C18 C 1.1048(4) 0.5192(2) 0.14495(13) 0.0476(6) Uani 1 1 d . . . . .
H18 H 1.1958 0.5723 0.1210 0.057 Uiso 1 1 calc R . . . .
C25 C 0.6179(5) 0.78585(18) 0.19340(13) 0.0479(6) Uani 1 1 d . . . . .
C10 C 0.6757(5) 0.29241(19) 0.32338(13) 0.0493(6) Uani 1 1 d . . . . .
C24 C 0.7098(5) 0.81526(19) 0.27460(13) 0.0495(6) Uani 1 1 d . . . . .
C14 C 1.0304(4) 0.3424(2) 0.16122(13) 0.0484(6) Uani 1 1 d . . . . .
H14 H 1.0676 0.2690 0.1488 0.058 Uiso 1 1 calc R . . . .
C3 C 0.4542(5) 0.2131(2) 0.32925(13) 0.0515(6) Uani 1 1 d . . . . .
C4 C 0.3447(5) 0.15227(19) 0.25071(14) 0.0486(6) Uani 1 1 d . . . . .
C8 C 0.4647(5) 0.15416(19) 0.12027(13) 0.0497(6) Uani 1 1 d . . . . .
H8 H 0.5799 0.1830 0.0870 0.060 Uiso 1 1 calc R . . . .
C29 C 0.6747(5) 0.6442(2) 0.07508(13) 0.0492(6) Uani 1 1 d . . . . .
H29 H 0.7502 0.5825 0.0495 0.059 Uiso 1 1 calc R . . . .
C20 C 0.9911(5) 0.7444(2) 0.35353(14) 0.0565(6) Uani 1 1 d . . . . .
H20 H 1.0974 0.6924 0.3579 0.068 Uiso 1 1 calc R . . . .
C7 C 0.2461(5) 0.0700(2) 0.09097(15) 0.0590(7) Uani 1 1 d . . . . .
H7 H 0.2121 0.0398 0.0364 0.071 Uiso 1 1 calc R . . . .
C28 C 0.5139(5) 0.6893(2) 0.03463(14) 0.0585(7) Uani 1 1 d . . . . .
H28 H 0.4791 0.6584 -0.0199 0.070 Uiso 1 1 calc R . . . .
C26 C 0.4544(6) 0.8282(2) 0.15117(15) 0.0617(7) Uani 1 1 d . . . . .
H26 H 0.3794 0.8903 0.1763 0.074 Uiso 1 1 calc R . . . .
C23 C 0.6773(6) 0.8998(2) 0.34006(15) 0.0632(7) Uani 1 1 d . . . . .
H23 H 0.5726 0.9526 0.3362 0.076 Uiso 1 1 calc R . . . .
C5 C 0.1228(5) 0.0684(2) 0.21851(17) 0.0616(7) Uani 1 1 d . . . . .
H5 H 0.0057 0.0392 0.2512 0.074 Uiso 1 1 calc R . . . .
C6 C 0.0751(5) 0.0283(2) 0.13888(17) 0.0652(7) Uani 1 1 d . . . . .
H6 H -0.0762 -0.0283 0.1169 0.078 Uiso 1 1 calc R . . . .
C21 C 0.9566(6) 0.8289(2) 0.41701(15) 0.0661(7) Uani 1 1 d . . . . .
H21 H 1.0410 0.8353 0.4661 0.079 Uiso 1 1 calc R . . . .
C11 C 0.8328(6) 0.3639(2) 0.38786(14) 0.0666(7) Uani 1 1 d . . . . .
H11 H 0.9849 0.4158 0.3829 0.080 Uiso 1 1 calc R . . . .
C27 C 0.4021(6) 0.7792(2) 0.07235(15) 0.0660(7) Uani 1 1 d . . . . .
H27 H 0.2882 0.8072 0.0435 0.079 Uiso 1 1 calc R . . . .
C22 C 0.8005(6) 0.9049(2) 0.41052(16) 0.0704(8) Uani 1 1 d . . . . .
H22 H 0.7781 0.9615 0.4554 0.084 Uiso 1 1 calc R . . . .
C2 C 0.3851(6) 0.2065(3) 0.40256(16) 0.0745(8) Uani 1 1 d . . . . .
H2 H 0.2365 0.1531 0.4080 0.089 Uiso 1 1 calc R . . . .
C12 C 0.7570(7) 0.3558(3) 0.45989(16) 0.0843(10) Uani 1 1 d . . . . .
H12 H 0.8583 0.4041 0.5053 0.101 Uiso 1 1 calc R . . . .
C1 C 0.5361(7) 0.2787(3) 0.46704(16) 0.0888(10) Uani 1 1 d . . . . .
H1 H 0.4883 0.2758 0.5172 0.107 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C17 1.419(3) . ?
N3 C30 1.409(3) . ?
N3 C19 1.405(3) . ?
N1 C13 1.419(3) . ?
N1 C9 1.412(3) . ?
N1 C10 1.399(3) . ?
N4 C18 1.336(3) . ?
N4 C14 1.340(3) . ?
N2 C16 1.146(3) . ?
C15 C17 1.399(3) . ?
C15 C13 1.400(3) . ?
C15 C16 1.445(3) . ?
C17 C18 1.385(3) . ?
C13 C14 1.383(3) . ?
C30 C25 1.407(3) . ?
C30 C29 1.392(3) . ?
C19 C24 1.400(3) . ?
C19 C20 1.392(3) . ?
C9 C4 1.403(3) . ?
C9 C8 1.391(3) . ?
C18 H18 0.9500 . ?
C25 C24 1.448(3) . ?
C25 C26 1.390(3) . ?
C10 C3 1.401(3) . ?
C10 C11 1.389(3) . ?
C24 C23 1.398(3) . ?
C14 H14 0.9500 . ?
C3 C4 1.454(3) . ?
C3 C2 1.395(3) . ?
C4 C5 1.399(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.380(3) . ?
C29 H29 0.9500 . ?
C29 C28 1.383(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.379(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.384(4) . ?
C28 H28 0.9500 . ?
C28 C27 1.393(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.381(4) . ?
C23 H23 0.9500 . ?
C23 C22 1.382(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(4) . ?
C6 H6 0.9500 . ?
C21 H21 0.9500 . ?
C21 C22 1.390(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(4) . ?
C27 H27 0.9500 . ?
C22 H22 0.9500 . ?
C2 H2 0.9500 . ?
C2 C1 1.378(4) . ?
C12 H12 0.9500 . ?
C12 C1 1.391(4) . ?
C1 H1 0.9500 . ?

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
C30 N3 C17 122.68(17) . . ?
C19 N3 C17 125.27(17) . . ?
C19 N3 C30 108.28(17) . . ?
C9 N1 C13 122.20(17) . . ?
C10 N1 C13 125.74(18) . . ?
C10 N1 C9 107.89(18) . . ?
C18 N4 C14 117.46(19) . . ?
C17 C15 C13 118.61(18) . . ?
C17 C15 C16 120.19(19) . . ?
C13 C15 C16 121.05(19) . . ?
C15 C17 N3 121.84(18) . . ?
C18 C17 N3 119.91(19) . . ?
C18 C17 C15 118.1(2) . . ?
C15 C13 N1 121.71(18) . . ?
C14 C13 N1 119.8(2) . . ?
C14 C13 C15 118.31(19) . . ?
C25 C30 N3 108.29(19) . . ?
C29 C30 N3 129.64(19) . . ?
C29 C30 C25 122.1(2) . . ?
C24 C19 N3 108.91(19) . . ?
C20 C19 N3 128.6(2) . . ?
C20 C19 C24 122.4(2) . . ?
N2 C16 C15 178.5(2) . . ?
C4 C9 N1 108.88(19) . . ?
C8 C9 N1 128.8(2) . . ?
C8 C9 C4 122.3(2) . . ?
N4 C18 C17 123.8(2) . . ?
N4 C18 H18 118.1 . . ?
C17 C18 H18 118.1 . . ?
C30 C25 C24 107.4(2) . . ?
C26 C25 C30 118.9(2) . . ?
C26 C25 C24 133.7(2) . . ?
N1 C10 C3 109.2(2) . . ?
C11 C10 N1 128.2(2) . . ?
C11 C10 C3 122.6(2) . . ?
C19 C24 C25 107.11(19) . . ?
C23 C24 C19 119.0(2) . . ?
C23 C24 C25 133.9(2) . . ?
N4 C14 C13 123.6(2) . . ?
N4 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
C10 C3 C4 107.07(19) . . ?
C2 C3 C10 119.0(2) . . ?
C2 C3 C4 133.9(2) . . ?
C9 C4 C3 106.90(19) . . ?
C5 C4 C9 118.4(2) . . ?
C5 C4 C3 134.6(2) . . ?
C9 C8 H8 121.4 . . ?
C7 C8 C9 117.3(2) . . ?
C7 C8 H8 121.4 . . ?
C30 C29 H29 121.3 . . ?
C28 C29 C30 117.5(2) . . ?
C28 C29 H29 121.3 . . ?
C19 C20 H20 121.3 . . ?
C21 C20 C19 117.4(3) . . ?
C21 C20 H20 121.3 . . ?
C8 C7 H7 119.1 . . ?
C8 C7 C6 121.8(2) . . ?
C6 C7 H7 119.1 . . ?
C29 C28 H28 119.4 . . ?
C29 C28 C27 121.2(2) . . ?
C27 C28 H28 119.4 . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.3(2) . . ?
C27 C26 H26 120.3 . . ?
C24 C23 H23 120.7 . . ?
C22 C23 C24 118.7(3) . . ?
C22 C23 H23 120.7 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C7 C6 H6 119.8 . . ?
C5 C6 C7 120.5(2) . . ?
C5 C6 H6 119.8 . . ?
C20 C21 H21 119.4 . . ?
C20 C21 C22 121.2(3) . . ?
C22 C21 H21 119.4 . . ?
C10 C11 H11 121.6 . . ?
C12 C11 C10 116.9(3) . . ?
C12 C11 H11 121.6 . . ?
C28 C27 H27 119.5 . . ?
C26 C27 C28 120.9(2) . . ?
C26 C27 H27 119.5 . . ?
C23 C22 C21 121.4(2) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C3 C2 H2 120.5 . . ?
C1 C2 C3 118.9(3) . . ?
C1 C2 H2 120.5 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C1 121.5(3) . . ?
C1 C12 H12 119.3 . . ?
C2 C1 C12 121.1(3) . . ?
C2 C1 H1 119.4 . . ?
C12 C1 H1 119.4 . . ?

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

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2027075'
loop_
_audit_author_name
_audit_author_address
'Zhiyong Ma'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2020-09-03 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_audit_creation_date             2019-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H18 N4'
_chemical_formula_sum            'C30 H18 N4'
_chemical_formula_weight         434.48
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   16.7453(8)
_cell_length_b                   13.9681(8)
_cell_length_c                   9.4885(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.658(3)
_cell_angle_gamma                90
_cell_volume                     2216.97(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6850
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.83
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            26798
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.347
_diffrn_reflns_theta_min         2.826
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    0.882
_reflns_Friedel_fraction_max     0.829
_reflns_number_gt                2980
_reflns_number_total             5062
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1108 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(10)
_refine_ls_extinction_coef       0.0104(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5062
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0724P)²+0.4360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1554
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C00F(H00F), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N001 N 0.31913(19) 0.3685(2) 0.3634(4) 0.0555(8) Uani 1 1 d . . . . .
N002 N 0.48977(19) 0.5359(2) 0.3749(4) 0.0535(8) Uani 1 1 d . . . . .
N003 N 0.4620(2) 0.2131(2) 0.5578(4) 0.0572(9) Uani 1 1 d . . . . .
N004 N 0.3035(3) 0.5857(3) 0.2000(4) 0.0707(11) Uani 1 1 d . . . . .
C005 C 0.4303(2) 0.2942(3) 0.4883(4) 0.0503(9) Uani 1 1 d . . . . .
C006 C 0.3522(3) 0.2945(3) 0.4325(4) 0.0555(10) Uani 1 1 d . . . . .
H006 H 0.3207 0.2388 0.4442 0.067 Uiso 1 1 calc R . . . .
C007 C 0.3659(2) 0.4455(3) 0.3461(4) 0.0524(9) Uani 1 1 d . . . . .
C008 C 0.5599(2) 0.5401(3) 0.3005(4) 0.0546(10) Uani 1 1 d . . . . .
C009 C 0.5425(3) 0.6856(3) 0.4071(5) 0.0606(11) Uani 1 1 d . . . . .
C00A C 0.4447(2) 0.4522(3) 0.3982(4) 0.0487(9) Uani 1 1 d . . . . .
C00B C 0.3307(2) 0.5234(3) 0.2653(5) 0.0567(10) Uani 1 1 d . . . . .
C00C C 0.4248(3) 0.1565(3) 0.6571(5) 0.0577(11) Uani 1 1 d . . . . .
C00D C 0.5928(3) 0.6323(3) 0.3163(5) 0.0621(11) Uani 1 1 d . . . . .
C00E C 0.4787(3) 0.6251(3) 0.4407(5) 0.0566(10) Uani 1 1 d . . . . .
C00F C 0.3512(3) 0.1694(3) 0.7174(5) 0.0672(12) Uani 1 1 d . . . . .
H00F H 0.3178 0.2224 0.6924 0.081 Uiso 1 1 calc R . . . .
C00G C 0.5374(3) 0.1732(3) 0.5343(5) 0.0587(11) Uani 1 1 d . . . . .
C00H C 0.4755(3) 0.0801(3) 0.6956(5) 0.0625(12) Uani 1 1 d . . . . .
C00I C 0.5469(3) 0.0908(3) 0.6178(5) 0.0632(12) Uani 1 1 d . . . . .
C00J C 0.4775(2) 0.3750(3) 0.4714(4) 0.0516(9) Uani 1 1 d . . . . .
H00J H 0.5310 0.3771 0.5092 0.062 Uiso 1 1 calc R . . . .
C00K C 0.5935(3) 0.4708(4) 0.2172(5) 0.0659(12) Uani 1 1 d . . . . .
H00K H 0.5707 0.4087 0.2078 0.079 Uiso 1 1 calc R . . . .
C00L C 0.5935(3) 0.1998(3) 0.4385(6) 0.0694(12) Uani 1 1 d . . . . .
H00L H 0.5857 0.2546 0.3800 0.083 Uiso 1 1 calc R . . . .
C00M C 0.4511(4) 0.0140(3) 0.7950(6) 0.0789(15) Uani 1 1 d . . . . .
H00M H 0.4846 -0.0383 0.8224 0.095 Uiso 1 1 calc R . . . .
C00N C 0.6619(3) 0.4957(5) 0.1480(6) 0.0823(15) Uani 1 1 d . . . . .
H00N H 0.6862 0.4499 0.0895 0.099 Uiso 1 1 calc R . . . .
C00O C 0.3286(3) 0.1022(4) 0.8150(6) 0.0783(14) Uani 1 1 d . . . . .
H00O H 0.2784 0.1084 0.8570 0.094 Uiso 1 1 calc R . . . .
C00P C 0.4191(3) 0.6540(3) 0.5271(5) 0.0653(12) Uani 1 1 d . . . . .
H00P H 0.3761 0.6127 0.5478 0.078 Uiso 1 1 calc R . . . .
C00Q C 0.5459(4) 0.7771(3) 0.4652(6) 0.0799(15) Uani 1 1 d . . . . .
H00Q H 0.5882 0.8194 0.4450 0.096 Uiso 1 1 calc R . . . .
C00R C 0.6173(4) 0.0368(4) 0.6076(6) 0.0841(16) Uani 1 1 d . . . . .
H00R H 0.6262 -0.0183 0.6651 0.101 Uiso 1 1 calc R . . . .
C00S C 0.3785(4) 0.0254(4) 0.8525(6) 0.0846(17) Uani 1 1 d . . . . .
H00S H 0.3615 -0.0199 0.9195 0.101 Uiso 1 1 calc R . . . .
C00T C 0.4246(4) 0.7455(4) 0.5823(6) 0.0795(15) Uani 1 1 d . . . . .
H00T H 0.3845 0.7676 0.6421 0.095 Uiso 1 1 calc R . . . .
C00U C 0.6606(3) 0.1440(4) 0.4316(7) 0.0848(16) Uani 1 1 d . . . . .
H00U H 0.7001 0.1612 0.3673 0.102 Uiso 1 1 calc R . . . .
C00V C 0.4873(4) 0.8052(4) 0.5519(6) 0.0885(17) Uani 1 1 d . . . . .
H00V H 0.4897 0.8674 0.5923 0.106 Uiso 1 1 calc R . . . .
C00W C 0.6951(3) 0.5856(5) 0.1628(7) 0.0898(17) Uani 1 1 d . . . . .
H00W H 0.7421 0.6001 0.1149 0.108 Uiso 1 1 calc R . . . .
C00X C 0.6618(3) 0.6550(4) 0.2451(6) 0.0779(15) Uani 1 1 d . . . . .
H00X H 0.6852 0.7168 0.2534 0.094 Uiso 1 1 calc R . . . .
C00Y C 0.6729(4) 0.0642(4) 0.5141(7) 0.0947(18) Uani 1 1 d . . . . .
H00Y H 0.7203 0.0276 0.5063 0.114 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N001 C006 1.331(5) . ?
N001 C007 1.346(5) . ?
N002 C008 1.399(5) . ?
N002 C00A 1.414(5) . ?
N002 C00E 1.409(5) . ?
N003 C005 1.402(5) . ?
N003 C00C 1.398(5) . ?
N003 C00G 1.407(5) . ?
N004 C00B 1.150(5) . ?
C005 C006 1.389(6) . ?
C005 C00J 1.390(5) . ?
C006 H006 0.9500 . ?
C007 C00A 1.391(5) . ?
C007 C00B 1.441(6) . ?
C008 C00D 1.407(6) . ?
C008 C00K 1.385(6) . ?
C009 C00D 1.440(7) . ?
C009 C00E 1.411(6) . ?
C009 C00Q 1.392(6) . ?
C00A C00J 1.382(5) . ?
C00C C00F 1.395(6) . ?
C00C C00H 1.402(6) . ?
C00D C00X 1.401(7) . ?
C00E C00P 1.381(6) . ?
C00F H00F 0.9500 . ?
C00F C00O 1.384(7) . ?
C00G C00I 1.402(6) . ?
C00G C00L 1.389(7) . ?
C00H C00I 1.442(7) . ?
C00H C00M 1.394(7) . ?
C00I C00R 1.407(7) . ?
C00J H00J 0.9500 . ?
C00K H00K 0.9500 . ?
C00K C00N 1.392(7) . ?
C00L H00L 0.9500 . ?
C00L C00U 1.373(7) . ?
C00M H00M 0.9500 . ?
C00M C00S 1.365(8) . ?
C00N H00N 0.9500 . ?
C00N C00W 1.377(8) . ?
C00O H00O 0.9500 . ?
C00O C00S 1.396(8) . ?
C00P H00P 0.9500 . ?
C00P C00T 1.382(7) . ?
C00Q H00Q 0.9500 . ?
C00Q C00V 1.366(8) . ?
C00R H00R 0.9500 . ?
C00R C00Y 1.370(9) . ?
C00S H00S 0.9500 . ?
C00T H00T 0.9500 . ?
C00T C00V 1.382(9) . ?
C00U H00U 0.9500 . ?
C00U C00Y 1.372(8) . ?
C00V H00V 0.9500 . ?
C00W H00W 0.9500 . ?
C00W C00X 1.378(8) . ?
C00X H00X 0.9500 . ?
C00Y H00Y 0.9500 . ?

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
C006 N001 C007 116.7(3) . . ?
C008 N002 C00A 125.4(3) . . ?
C008 N002 C00E 108.5(3) . . ?
C00E N002 C00A 125.4(3) . . ?
C005 N003 C00G 124.6(4) . . ?
C00C N003 C005 127.1(3) . . ?
C00C N003 C00G 108.2(3) . . ?
C006 C005 N003 120.7(3) . . ?
C006 C005 C00J 118.9(4) . . ?
C00J C005 N003 120.4(3) . . ?
N001 C006 C005 123.6(4) . . ?
N001 C006 H006 118.2 . . ?
C005 C006 H006 118.2 . . ?
N001 C007 C00A 124.0(4) . . ?
N001 C007 C00B 116.3(3) . . ?
C00A C007 C00B 119.7(4) . . ?
N002 C008 C00D 108.5(4) . . ?
C00K C008 N002 129.2(4) . . ?
C00K C008 C00D 122.2(4) . . ?
C00E C009 C00D 107.2(4) . . ?
C00Q C009 C00D 134.3(4) . . ?
C00Q C009 C00E 118.5(5) . . ?
C007 C00A N002 120.3(3) . . ?
C00J C00A N002 121.5(3) . . ?
C00J C00A C007 118.3(3) . . ?
N004 C00B C007 179.1(5) . . ?
N003 C00C C00H 108.9(4) . . ?
C00F C00C N003 129.3(4) . . ?
C00F C00C C00H 121.8(4) . . ?
C008 C00D C009 107.4(4) . . ?
C00X C00D C008 118.9(5) . . ?
C00X C00D C009 133.6(4) . . ?
N002 C00E C009 108.2(4) . . ?
C00P C00E N002 129.4(4) . . ?
C00P C00E C009 122.3(4) . . ?
C00C C00F H00F 121.3 . . ?
C00O C00F C00C 117.5(5) . . ?
C00O C00F H00F 121.3 . . ?
C00I C00G N003 108.4(4) . . ?
C00L C00G N003 129.5(4) . . ?
C00L C00G C00I 121.8(4) . . ?
C00C C00H C00I 107.1(4) . . ?
C00M C00H C00C 119.2(5) . . ?
C00M C00H C00I 133.7(4) . . ?
C00G C00I C00H 107.4(4) . . ?
C00G C00I C00R 118.4(5) . . ?
C00R C00I C00H 134.2(5) . . ?
C005 C00J H00J 120.7 . . ?
C00A C00J C005 118.5(4) . . ?
C00A C00J H00J 120.7 . . ?
C008 C00K H00K 121.3 . . ?
C008 C00K C00N 117.4(5) . . ?
C00N C00K H00K 121.3 . . ?
C00G C00L H00L 121.3 . . ?
C00U C00L C00G 117.4(5) . . ?
C00U C00L H00L 121.3 . . ?
C00H C00M H00M 120.4 . . ?
C00S C00M C00H 119.1(5) . . ?
C00S C00M H00M 120.4 . . ?
C00K C00N H00N 119.5 . . ?
C00W C00N C00K 121.1(5) . . ?
C00W C00N H00N 119.5 . . ?
C00F C00O H00O 119.6 . . ?
C00F C00O C00S 120.9(5) . . ?
C00S C00O H00O 119.6 . . ?
C00E C00P H00P 121.4 . . ?
C00E C00P C00T 117.3(5) . . ?
C00T C00P H00P 121.4 . . ?
C009 C00Q H00Q 120.5 . . ?
C00V C00Q C009 119.0(5) . . ?
C00V C00Q H00Q 120.5 . . ?
C00I C00R H00R 120.3 . . ?
C00Y C00R C00I 119.4(5) . . ?
C00Y C00R H00R 120.3 . . ?
C00M C00S C00O 121.5(5) . . ?
C00M C00S H00S 119.3 . . ?
C00O C00S H00S 119.3 . . ?
C00P C00T H00T 119.5 . . ?
C00P C00T C00V 121.1(5) . . ?
C00V C00T H00T 119.5 . . ?
C00L C00U H00U 118.8 . . ?
C00Y C00U C00L 122.4(6) . . ?
C00Y C00U H00U 118.8 . . ?
C00Q C00V C00T 121.7(5) . . ?
C00Q C00V H00V 119.1 . . ?
C00T C00V H00V 119.1 . . ?
C00N C00W H00W 119.1 . . ?
C00N C00W C00X 121.9(5) . . ?
C00X C00W H00W 119.1 . . ?
C00D C00X H00X 120.7 . . ?
C00W C00X C00D 118.5(5) . . ?
C00W C00X H00X 120.7 . . ?
C00R C00Y C00U 120.6(5) . . ?
C00R C00Y H00Y 119.7 . . ?
C00U C00Y H00Y 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
