# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_140902b_0m
_database_code_depnum_ccdc_archive 'CCDC 2072684'
loop_
_audit_author_name
_audit_author_address
'Shaoyin Wang'
;Wannan Medical College
China
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-21 downloaded from the CCDC.
;
_audit_creation_date             2021-03-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C30 H22 N4, [+ solvents]'
_chemical_formula_sum            'C30 H22 N4'
_chemical_formula_weight         438.51
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.3091(8)
_cell_length_b                   14.2045(9)
_cell_length_c                   16.5877(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.9730(10)
_cell_angle_gamma                90
_cell_volume                     2837.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8019
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.799
_cell_measurement_theta_min      2.217
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.027
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23952
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.440
_diffrn_reflns_theta_min         1.885
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4408
_reflns_number_total             6452
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         6452
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.109
_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)+(0.0745P)²+0.0612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1444
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Rigid bond restraints
 C26, C27
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C24(H24), C14(H14), C20(H20), C23(H23), C22(H22), C15(H15),
 C21(H21), C4(H4), C3(H3), C2(H2), C30(H30), C18(H18), C16(H16), C26(H26),
 C28(H28), C29(H29), C17(H17), C27(H27)
;
_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
C11 C -0.07948(10) 0.43693(9) 0.26446(8) 0.0412(3) Uani 1 1 d . . . . .
N2 N -0.16781(9) 0.48622(8) 0.27914(7) 0.0468(3) Uani 1 1 d . . . . .
C19 C 0.07916(10) 0.42826(8) 0.19440(8) 0.0377(3) Uani 1 1 d . . . . .
C10 C 0.02594(10) 0.48662(9) 0.25424(7) 0.0375(3) Uani 1 1 d . . . . .
C7 C -0.00823(10) 0.58345(9) 0.21953(8) 0.0396(3) Uani 1 1 d . . . . .
N1 N -0.11034(10) 0.71573(8) 0.19945(8) 0.0544(3) Uani 1 1 d . . . . .
H1 H -0.163273 0.754880 0.200676 0.065 Uiso 1 1 calc R U . . .
C13 C 0.10450(11) 0.49845(9) 0.33937(8) 0.0402(3) Uani 1 1 d . . . . .
N4 N -0.21450(11) 0.34382(9) 0.28607(9) 0.0602(3) Uani 1 1 d . . . . .
N3 N -0.24990(10) 0.42989(10) 0.29181(9) 0.0602(3) Uani 1 1 d . . . . .
C12 C -0.11131(11) 0.34432(10) 0.26875(9) 0.0468(3) Uani 1 1 d . . . . .
C6 C 0.04683(11) 0.64978(9) 0.17520(8) 0.0400(3) Uani 1 1 d . . . . .
C5 C 0.14358(12) 0.64950(10) 0.14308(9) 0.0481(3) Uani 1 1 d . . . . .
H5 H 0.189405 0.596829 0.148577 0.058 Uiso 1 1 calc R U . . .
C1 C -0.02058(12) 0.73154(9) 0.16427(9) 0.0480(3) Uani 1 1 d . . . . .
C24 C 0.03008(11) 0.42834(10) 0.11097(8) 0.0462(3) Uani 1 1 d . . . . .
H24 H -0.032183 0.465416 0.091788 0.055 Uiso 1 1 calc R U . . .
C14 C 0.19953(12) 0.55185(11) 0.34688(10) 0.0556(4) Uani 1 1 d . . . . .
H14 H 0.216788 0.578773 0.299993 0.067 Uiso 1 1 calc R U . . .
C20 C 0.17087(12) 0.37246(11) 0.22099(9) 0.0527(4) Uani 1 1 d . . . . .
H20 H 0.204942 0.371618 0.276543 0.063 Uiso 1 1 calc R U . . .
C9 C -0.18424(12) 0.58751(10) 0.27620(10) 0.0542(4) Uani 1 1 d . . . . .
H9A H -0.173282 0.613073 0.331521 0.065 Uiso 1 1 calc R U . . .
H9B H -0.258948 0.602690 0.247107 0.065 Uiso 1 1 calc R U . . .
C8 C -0.10134(11) 0.62734(10) 0.23216(9) 0.0455(3) Uani 1 1 d . . . . .
C25 C -0.05720(12) 0.25356(10) 0.25665(10) 0.0525(4) Uani 1 1 d . . . . .
C23 C 0.07350(14) 0.37351(12) 0.05643(10) 0.0588(4) Uani 1 1 d . . . . .
H23 H 0.040508 0.374262 0.000663 0.071 Uiso 1 1 calc R U . . .
C22 C 0.16453(16) 0.31820(13) 0.08382(11) 0.0702(5) Uani 1 1 d . . . . .
H22 H 0.193407 0.281251 0.046999 0.084 Uiso 1 1 calc R U . . .
C15 C 0.26964(13) 0.56635(12) 0.42218(11) 0.0632(4) Uani 1 1 d . . . . .
H15 H 0.333085 0.602883 0.425361 0.076 Uiso 1 1 calc R U . . .
C21 C 0.21268(15) 0.31772(13) 0.16580(11) 0.0713(5) Uani 1 1 d . . . . .
H21 H 0.274468 0.279981 0.184660 0.086 Uiso 1 1 calc R U . . .
C4 C 0.16926(14) 0.72874(11) 0.10331(10) 0.0577(4) Uani 1 1 d . . . . .
H4 H 0.233446 0.729107 0.082011 0.069 Uiso 1 1 calc R U . . .
C3 C 0.10186(15) 0.80869(12) 0.09391(10) 0.0644(4) Uani 1 1 d . . . . .
H3 H 0.121950 0.861100 0.066741 0.077 Uiso 1 1 calc R U . . .
C2 C 0.00710(14) 0.81089(11) 0.12402(10) 0.0599(4) Uani 1 1 d . . . . .
H2 H -0.037873 0.864113 0.117794 0.072 Uiso 1 1 calc R U . . .
C30 C -0.06935(15) 0.21562(12) 0.17875(12) 0.0701(5) Uani 1 1 d . . . . .
H30 H -0.106025 0.249337 0.133091 0.084 Uiso 1 1 calc R U . . .
C18 C 0.08315(16) 0.45961(15) 0.40939(10) 0.0775(6) Uani 1 1 d . . . . .
H18 H 0.019924 0.422856 0.406438 0.093 Uiso 1 1 calc R U . . .
C16 C 0.24685(16) 0.52768(14) 0.49195(10) 0.0721(5) Uani 1 1 d . . . . .
H16 H 0.293541 0.537794 0.542949 0.087 Uiso 1 1 calc R U . . .
C26 C -0.00275(19) 0.20165(14) 0.32244(14) 0.0863(6) Uani 1 1 d . U . . .
H26 H 0.006057 0.225642 0.375574 0.104 Uiso 1 1 calc R U . . .
C28 C 0.0282(2) 0.07704(16) 0.2338(2) 0.1015(8) Uani 1 1 d . . . . .
H28 H 0.057951 0.018345 0.226118 0.122 Uiso 1 1 calc R U . . .
C29 C -0.0266(2) 0.12692(16) 0.16871(17) 0.0912(6) Uani 1 1 d . . . . .
H29 H -0.036007 0.101367 0.116102 0.109 Uiso 1 1 calc R U . . .
C17 C 0.1538(2) 0.47379(19) 0.48501(11) 0.1013(8) Uani 1 1 d . . . . .
H17 H 0.137483 0.446034 0.531875 0.122 Uiso 1 1 calc R U . . .
C27 C 0.0394(2) 0.11321(17) 0.3099(2) 0.1088(8) Uani 1 1 d . U . . .
H27 H 0.075870 0.078513 0.355002 0.131 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
C11 N2 1.3571(17) . ?
C11 C10 1.5172(17) . ?
C11 C12 1.3787(19) . ?
N2 N3 1.3392(16) . ?
N2 C9 1.4523(19) . ?
C19 C10 1.5400(17) . ?
C19 C24 1.3903(18) . ?
C19 C20 1.3750(18) . ?
C10 C7 1.5164(18) . ?
C10 C13 1.5462(17) . ?
C7 C6 1.4472(18) . ?
C7 C8 1.3586(18) . ?
N1 H1 0.8600 . ?
N1 C1 1.3709(19) . ?
N1 C8 1.3632(18) . ?
C13 C14 1.378(2) . ?
C13 C18 1.360(2) . ?
N4 N3 1.3079(18) . ?
N4 C12 1.3592(18) . ?
C12 C25 1.484(2) . ?
C6 C5 1.4019(19) . ?
C6 C1 1.4169(18) . ?
C5 H5 0.9300 . ?
C5 C4 1.374(2) . ?
C1 C2 1.388(2) . ?
C24 H24 0.9300 . ?
C24 C23 1.383(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.379(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.485(2) . ?
C25 C30 1.379(2) . ?
C25 C26 1.371(2) . ?
C23 H23 0.9300 . ?
C23 C22 1.367(2) . ?
C22 H22 0.9300 . ?
C22 C21 1.366(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.362(2) . ?
C21 H21 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.396(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.361(2) . ?
C2 H2 0.9300 . ?
C30 H30 0.9300 . ?
C30 C29 1.388(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.385(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.362(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.391(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.350(3) . ?
C28 C27 1.343(4) . ?
C29 H29 0.9300 . ?
C17 H17 0.9300 . ?
C27 H27 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C11 C10 121.04(12) . . ?
N2 C11 C12 103.66(11) . . ?
C12 C11 C10 135.11(12) . . ?
C11 N2 C9 128.04(11) . . ?
N3 N2 C11 112.25(11) . . ?
N3 N2 C9 119.53(11) . . ?
C24 C19 C10 119.08(11) . . ?
C20 C19 C10 122.30(11) . . ?
C20 C19 C24 118.56(12) . . ?
C11 C10 C19 108.04(10) . . ?
C11 C10 C13 109.62(10) . . ?
C19 C10 C13 112.21(10) . . ?
C7 C10 C11 106.75(10) . . ?
C7 C10 C19 111.41(10) . . ?
C7 C10 C13 108.65(10) . . ?
C6 C7 C10 131.39(11) . . ?
C8 C7 C10 122.28(12) . . ?
C8 C7 C6 106.18(12) . . ?
C1 N1 H1 125.8 . . ?
C8 N1 H1 125.8 . . ?
C8 N1 C1 108.31(11) . . ?
C14 C13 C10 120.05(12) . . ?
C18 C13 C10 122.74(12) . . ?
C18 C13 C14 117.19(13) . . ?
N3 N4 C12 110.53(12) . . ?
N4 N3 N2 105.87(11) . . ?
C11 C12 C25 132.98(13) . . ?
N4 C12 C11 107.69(12) . . ?
N4 C12 C25 119.31(12) . . ?
C5 C6 C7 135.68(12) . . ?
C5 C6 C1 118.34(12) . . ?
C1 C6 C7 105.97(11) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 C6 118.57(14) . . ?
C4 C5 H5 120.7 . . ?
N1 C1 C6 108.28(12) . . ?
N1 C1 C2 129.62(13) . . ?
C2 C1 C6 122.10(14) . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.25(13) . . ?
C23 C24 H24 119.9 . . ?
C13 C14 H14 119.2 . . ?
C13 C14 C15 121.63(14) . . ?
C15 C14 H14 119.2 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.43(14) . . ?
C21 C20 H20 119.8 . . ?
N2 C9 H9A 110.4 . . ?
N2 C9 H9B 110.4 . . ?
N2 C9 C8 106.80(11) . . ?
H9A C9 H9B 108.6 . . ?
C8 C9 H9A 110.4 . . ?
C8 C9 H9B 110.4 . . ?
C7 C8 N1 111.27(12) . . ?
C7 C8 C9 126.08(13) . . ?
N1 C8 C9 122.65(12) . . ?
C30 C25 C12 120.12(14) . . ?
C26 C25 C12 121.23(16) . . ?
C26 C25 C30 118.40(17) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 C24 120.52(15) . . ?
C22 C23 H23 119.7 . . ?
C23 C22 H22 120.3 . . ?
C21 C22 C23 119.36(15) . . ?
C21 C22 H22 120.3 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.61(15) . . ?
C16 C15 H15 119.7 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.88(15) . . ?
C22 C21 H21 119.6 . . ?
C5 C4 H4 119.0 . . ?
C5 C4 C3 121.96(15) . . ?
C3 C4 H4 119.0 . . ?
C4 C3 H3 119.6 . . ?
C2 C3 C4 120.83(15) . . ?
C2 C3 H3 119.6 . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.18(15) . . ?
C3 C2 H2 120.9 . . ?
C25 C30 H30 120.1 . . ?
C25 C30 C29 119.78(19) . . ?
C29 C30 H30 120.1 . . ?
C13 C18 H18 119.4 . . ?
C13 C18 C17 121.22(16) . . ?
C17 C18 H18 119.4 . . ?
C15 C16 H16 120.9 . . ?
C15 C16 C17 118.20(16) . . ?
C17 C16 H16 120.9 . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.2(2) . . ?
C27 C26 H26 119.9 . . ?
C29 C28 H28 120.4 . . ?
C27 C28 H28 120.4 . . ?
C27 C28 C29 119.2(2) . . ?
C30 C29 H29 119.4 . . ?
C28 C29 C30 121.3(2) . . ?
C28 C29 H29 119.4 . . ?
C18 C17 H17 119.4 . . ?
C16 C17 C18 121.14(17) . . ?
C16 C17 H17 119.4 . . ?
C26 C27 H27 119.4 . . ?
C28 C27 C26 121.2(2) . . ?
C28 C27 H27 119.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 N4 0.86 2.01 2.8690(17) 175.1 2_455 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N2 N3 N4 0.54(16) . . . . ?
C11 N2 C9 C8 15.14(19) . . . . ?
C11 C10 C7 C6 -158.98(13) . . . . ?
C11 C10 C7 C8 26.26(16) . . . . ?
C11 C10 C13 C14 -172.04(13) . . . . ?
C11 C10 C13 C18 6.49(19) . . . . ?
C11 C12 C25 C30 -86.3(2) . . . . ?
C11 C12 C25 C26 99.5(2) . . . . ?
N2 C11 C10 C19 -148.90(12) . . . . ?
N2 C11 C10 C7 -28.97(16) . . . . ?
N2 C11 C10 C13 88.54(14) . . . . ?
N2 C11 C12 N4 -0.46(15) . . . . ?
N2 C11 C12 C25 177.94(15) . . . . ?
N2 C9 C8 C7 -18.06(19) . . . . ?
N2 C9 C8 N1 162.61(13) . . . . ?
C19 C10 C7 C6 -41.25(18) . . . . ?
C19 C10 C7 C8 143.99(12) . . . . ?
C19 C10 C13 C14 67.92(16) . . . . ?
C19 C10 C13 C18 -113.56(16) . . . . ?
C19 C24 C23 C22 0.4(2) . . . . ?
C19 C20 C21 C22 0.4(3) . . . . ?
C10 C11 N2 N3 -175.79(12) . . . . ?
C10 C11 N2 C9 9.2(2) . . . . ?
C10 C11 C12 N4 174.38(14) . . . . ?
C10 C11 C12 C25 -7.2(3) . . . . ?
C10 C19 C24 C23 -177.31(13) . . . . ?
C10 C19 C20 C21 176.79(15) . . . . ?
C10 C7 C6 C5 5.3(3) . . . . ?
C10 C7 C6 C1 -175.44(13) . . . . ?
C10 C7 C8 N1 176.09(12) . . . . ?
C10 C7 C8 C9 -3.3(2) . . . . ?
C10 C13 C14 C15 177.93(14) . . . . ?
C10 C13 C18 C17 -178.19(19) . . . . ?
C7 C10 C13 C14 -55.73(16) . . . . ?
C7 C10 C13 C18 122.80(16) . . . . ?
C7 C6 C5 C4 179.90(15) . . . . ?
C7 C6 C1 N1 -0.09(15) . . . . ?
C7 C6 C1 C2 179.72(13) . . . . ?
N1 C1 C2 C3 -179.73(15) . . . . ?
C13 C10 C7 C6 82.87(16) . . . . ?
C13 C10 C7 C8 -91.89(14) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C13 C18 C17 C16 0.4(4) . . . . ?
N4 C12 C25 C30 91.97(18) . . . . ?
N4 C12 C25 C26 -82.2(2) . . . . ?
N3 N2 C9 C8 -159.54(12) . . . . ?
N3 N4 C12 C11 0.84(17) . . . . ?
N3 N4 C12 C25 -177.83(13) . . . . ?
C12 C11 N2 N3 -0.04(15) . . . . ?
C12 C11 N2 C9 -175.03(13) . . . . ?
C12 C11 C10 C19 36.9(2) . . . . ?
C12 C11 C10 C7 156.88(15) . . . . ?
C12 C11 C10 C13 -85.61(18) . . . . ?
C12 N4 N3 N2 -0.83(17) . . . . ?
C12 C25 C30 C29 -174.44(16) . . . . ?
C12 C25 C26 C27 174.67(19) . . . . ?
C6 C7 C8 N1 0.18(15) . . . . ?
C6 C7 C8 C9 -179.22(13) . . . . ?
C6 C5 C4 C3 -0.2(2) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
C5 C6 C1 N1 179.34(12) . . . . ?
C5 C6 C1 C2 -0.8(2) . . . . ?
C5 C4 C3 C2 -0.2(3) . . . . ?
C1 N1 C8 C7 -0.24(16) . . . . ?
C1 N1 C8 C9 179.18(13) . . . . ?
C1 C6 C5 C4 0.68(19) . . . . ?
C24 C19 C10 C11 72.93(14) . . . . ?
C24 C19 C10 C7 -44.02(15) . . . . ?
C24 C19 C10 C13 -166.11(11) . . . . ?
C24 C19 C20 C21 -0.2(2) . . . . ?
C24 C23 C22 C21 -0.2(3) . . . . ?
C14 C13 C18 C17 0.4(3) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C20 C19 C10 C11 -104.03(14) . . . . ?
C20 C19 C10 C7 139.02(13) . . . . ?
C20 C19 C10 C13 16.94(17) . . . . ?
C20 C19 C24 C23 -0.2(2) . . . . ?
C9 N2 N3 N4 176.01(13) . . . . ?
C8 C7 C6 C5 -179.33(15) . . . . ?
C8 C7 C6 C1 -0.05(14) . . . . ?
C8 N1 C1 C6 0.20(15) . . . . ?
C8 N1 C1 C2 -179.59(15) . . . . ?
C25 C30 C29 C28 -0.9(3) . . . . ?
C25 C26 C27 C28 0.3(4) . . . . ?
C23 C22 C21 C20 -0.2(3) . . . . ?
C15 C16 C17 C18 -0.9(4) . . . . ?
C4 C3 C2 C1 0.0(2) . . . . ?
C30 C25 C26 C27 0.4(3) . . . . ?
C18 C13 C14 C15 -0.7(2) . . . . ?
C26 C25 C30 C29 -0.1(3) . . . . ?
C29 C28 C27 C26 -1.2(4) . . . . ?
C27 C28 C29 C30 1.5(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 13.3 0.2 ?
2 0.000 0.000 0.500 388.4 4.5 '2 ?'
3 0.500 0.500 1.000 388.4 4.5 '2 ?'
4 0.500 0.500 0.500 13.3 0.2 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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_140601a_0m
_database_code_depnum_ccdc_archive 'CCDC 2072685'
loop_
_audit_author_name
_audit_author_address
'Shaoyin Wang'
;Wannan Medical College
China
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-21 downloaded from the CCDC.
;
_audit_creation_date             2021-03-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C30 H22 N2'
_chemical_formula_sum            'C30 H22 N2'
_chemical_formula_weight         410.49
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.5637(13)
_cell_length_b                   10.7601(10)
_cell_length_c                   16.2434(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.0770(10)
_cell_angle_gamma                90
_cell_volume                     2520.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5141
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.215
_cell_measurement_theta_min      2.277
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_correction_T_min  0.9918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.082
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21431
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.627
_diffrn_reflns_theta_min         2.277
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_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                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3470
_reflns_number_total             5806
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0032(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5806
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.004
_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)+(0.0605P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1252
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26),
  C27(H27), C28(H28), C29(H29), C30(H30), N1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.11778(9) 0.02917(12) 0.28124(8) 0.0477(3) Uani 1 1 d . . . . .
C2 C 0.21326(9) 0.02127(11) 0.28788(8) 0.0445(3) Uani 1 1 d . . . . .
C3 C 0.23982(9) -0.08776(12) 0.33684(8) 0.0483(3) Uani 1 1 d . . . . .
C4 C 0.32460(11) -0.14460(13) 0.36667(9) 0.0619(4) Uani 1 1 d . . . . .
H4 H 0.380139 -0.111398 0.354609 0.074 Uiso 1 1 calc R U . . .
C5 C 0.32407(13) -0.25041(15) 0.41411(10) 0.0730(5) Uani 1 1 d . . . . .
H5 H 0.379962 -0.288635 0.434394 0.088 Uiso 1 1 calc R U . . .
C6 C 0.24093(15) -0.30155(15) 0.43240(10) 0.0734(5) Uani 1 1 d . . . . .
H6 H 0.242807 -0.373561 0.464260 0.088 Uiso 1 1 calc R U . . .
C7 C 0.15724(13) -0.24852(14) 0.40470(9) 0.0650(4) Uani 1 1 d . . . . .
H7 H 0.102238 -0.282909 0.417148 0.078 Uiso 1 1 calc R U . . .
C8 C 0.15727(10) -0.14067(12) 0.35697(8) 0.0522(4) Uani 1 1 d . . . . .
C9 C 0.26937(8) 0.10289(11) 0.24388(8) 0.0440(3) Uani 1 1 d . . . . .
C10 C 0.24349(9) 0.21919(12) 0.22245(9) 0.0468(3) Uani 1 1 d . . . . .
C11 C 0.15919(9) 0.28751(12) 0.24418(8) 0.0446(3) Uani 1 1 d . . . . .
C12 C 0.05702(9) 0.11319(14) 0.23004(9) 0.0544(4) Uani 1 1 d . . . . .
H12 H -0.001860 0.082497 0.211120 0.065 Uiso 1 1 calc R U . . .
C13 C 0.35482(10) 0.05226(13) 0.21531(9) 0.0541(4) Uani 1 1 d . . . . .
C14 C 0.43718(11) 0.11731(17) 0.22876(14) 0.0836(6) Uani 1 1 d . . . . .
H14 H 0.439729 0.191666 0.258177 0.100 Uiso 1 1 calc R U . . .
C15 C 0.51531(15) 0.0748(3) 0.1997(2) 0.1216(9) Uani 1 1 d . . . . .
H15 H 0.570407 0.119401 0.210122 0.146 Uiso 1 1 calc R U . . .
C16 C 0.5119(2) -0.0335(3) 0.1554(2) 0.1320(11) Uani 1 1 d . . . . .
H16 H 0.564664 -0.061880 0.135026 0.158 Uiso 1 1 calc R U . . .
C17 C 0.43075(19) -0.1010(2) 0.14082(14) 0.1056(7) Uani 1 1 d . . . . .
H17 H 0.428484 -0.174722 0.110671 0.127 Uiso 1 1 calc R U . . .
C18 C 0.35258(13) -0.05781(15) 0.17159(11) 0.0725(5) Uani 1 1 d . . . . .
H18 H 0.297939 -0.103624 0.162638 0.087 Uiso 1 1 calc R U . . .
C19 C 0.15802(9) 0.41539(12) 0.20068(8) 0.0457(3) Uani 1 1 d . . . . .
C20 C 0.12564(11) 0.42435(14) 0.11621(9) 0.0611(4) Uani 1 1 d . . . . .
H20 H 0.102401 0.353958 0.087239 0.073 Uiso 1 1 calc R U . . .
C21 C 0.12740(13) 0.53548(16) 0.07482(10) 0.0757(5) Uani 1 1 d . . . . .
H21 H 0.105486 0.539564 0.018285 0.091 Uiso 1 1 calc R U . . .
C22 C 0.16128(14) 0.64038(16) 0.11637(11) 0.0804(5) Uani 1 1 d . . . . .
H22 H 0.161588 0.715861 0.088518 0.096 Uiso 1 1 calc R U . . .
C23 C 0.19471(14) 0.63274(14) 0.19949(11) 0.0801(5) Uani 1 1 d . . . . .
H23 H 0.218985 0.703097 0.227872 0.096 Uiso 1 1 calc R U . . .
C24 C 0.19256(12) 0.52128(13) 0.24128(9) 0.0634(4) Uani 1 1 d . . . . .
H24 H 0.214812 0.517718 0.297765 0.076 Uiso 1 1 calc R U . . .
C25 C 0.15887(10) 0.30688(12) 0.33797(8) 0.0497(3) Uani 1 1 d . . . . .
C26 C 0.23973(12) 0.31126(14) 0.39306(9) 0.0648(4) Uani 1 1 d . . . . .
H26 H 0.295668 0.291766 0.374707 0.078 Uiso 1 1 calc R U . . .
C27 C 0.23913(16) 0.34430(16) 0.47555(11) 0.0834(6) Uani 1 1 d . . . . .
H27 H 0.294491 0.347395 0.511832 0.100 Uiso 1 1 calc R U . . .
C28 C 0.15726(19) 0.37236(17) 0.50367(12) 0.0891(6) Uani 1 1 d . . . . .
H28 H 0.156830 0.395731 0.558737 0.107 Uiso 1 1 calc R U . . .
C29 C 0.07659(16) 0.36577(16) 0.45040(12) 0.0853(6) Uani 1 1 d . . . . .
H29 H 0.020772 0.383246 0.469621 0.102 Uiso 1 1 calc R U . . .
C30 C 0.07647(12) 0.33333(14) 0.36778(10) 0.0646(4) Uani 1 1 d . . . . .
H30 H 0.020697 0.329306 0.332127 0.078 Uiso 1 1 calc R U . . .
H10 H 0.2797(9) 0.2628(12) 0.1882(8) 0.050(4) Uiso 1 1 d . . . . .
N1 N 0.08488(8) -0.06961(11) 0.32175(7) 0.0571(3) Uani 1 1 d . . . . .
H1 H 0.027360 -0.084407 0.324476 0.069 Uiso 1 1 calc R U . . .
N2 N 0.07285(7) 0.22388(11) 0.20707(7) 0.0523(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3821(18) . ?
C1 C12 1.444(2) . ?
C1 N1 1.3713(16) . ?
C2 C3 1.4394(18) . ?
C2 C9 1.4539(17) . ?
C3 C4 1.4018(19) . ?
C3 C8 1.4096(18) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.364(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.396(2) . ?
C8 N1 1.3615(18) . ?
C9 C10 1.3387(18) . ?
C9 C13 1.4911(18) . ?
C10 C11 1.5147(17) . ?
C10 H10 0.944(13) . ?
C11 C19 1.5459(18) . ?
C11 C25 1.5383(18) . ?
C11 N2 1.4833(16) . ?
C12 H12 0.9300 . ?
C12 N2 1.2787(17) . ?
C13 C14 1.379(2) . ?
C13 C18 1.379(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.370(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.367(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.3902(19) . ?
C19 C24 1.3757(19) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.371(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.372(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.381(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.376(2) . ?
C25 C30 1.3851(19) . ?
C26 H26 0.9300 . ?
C26 C27 1.387(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.369(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.360(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.386(2) . ?
C30 H30 0.9300 . ?
N1 H1 0.8600 . ?

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
C2 C1 C12 127.71(12) . . ?
N1 C1 C2 109.29(12) . . ?
N1 C1 C12 122.31(12) . . ?
C1 C2 C3 106.41(11) . . ?
C1 C2 C9 123.60(12) . . ?
C3 C2 C9 129.63(12) . . ?
C4 C3 C2 134.58(13) . . ?
C4 C3 C8 118.82(13) . . ?
C8 C3 C2 106.59(12) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.75(15) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.17(16) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.69(15) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 121.3 . . ?
C6 C7 C8 117.46(15) . . ?
C8 C7 H7 121.3 . . ?
C7 C8 C3 122.11(15) . . ?
N1 C8 C3 108.12(12) . . ?
N1 C8 C7 129.77(14) . . ?
C2 C9 C13 118.92(11) . . ?
C10 C9 C2 122.36(12) . . ?
C10 C9 C13 118.51(11) . . ?
C9 C10 C11 126.93(12) . . ?
C9 C10 H10 117.3(8) . . ?
C11 C10 H10 115.7(8) . . ?
C10 C11 C19 106.42(10) . . ?
C10 C11 C25 114.33(11) . . ?
C25 C11 C19 109.31(10) . . ?
N2 C11 C10 110.48(10) . . ?
N2 C11 C19 105.72(10) . . ?
N2 C11 C25 110.17(10) . . ?
C1 C12 H12 115.5 . . ?
N2 C12 C1 129.07(13) . . ?
N2 C12 H12 115.5 . . ?
C14 C13 C9 120.70(14) . . ?
C18 C13 C9 120.91(13) . . ?
C18 C13 C14 118.33(15) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.4(2) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.2(2) . . ?
C18 C17 H17 120.4 . . ?
C13 C18 C17 120.84(19) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C11 119.55(12) . . ?
C24 C19 C11 122.57(12) . . ?
C24 C19 C20 117.78(13) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.08(14) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.40(15) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.4 . . ?
C21 C22 C23 119.24(15) . . ?
C23 C22 H22 120.4 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.43(16) . . ?
C24 C23 H23 119.8 . . ?
C19 C24 C23 121.05(15) . . ?
C19 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C26 C25 C11 121.82(13) . . ?
C26 C25 C30 118.03(14) . . ?
C30 C25 C11 119.82(13) . . ?
C25 C26 H26 119.5 . . ?
C25 C26 C27 121.06(17) . . ?
C27 C26 H26 119.5 . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.17(18) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 120.3 . . ?
C29 C28 C27 119.43(17) . . ?
C29 C28 H28 120.3 . . ?
C28 C29 H29 119.6 . . ?
C28 C29 C30 120.84(18) . . ?
C30 C29 H29 119.6 . . ?
C25 C30 C29 120.45(17) . . ?
C25 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C1 N1 H1 125.2 . . ?
C8 N1 C1 109.56(11) . . ?
C8 N1 H1 125.2 . . ?
C12 N2 C11 119.25(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 N2 0.86 2.54 3.1830(16) 132.6 2_545 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -178.48(15) . . . . ?
C1 C2 C3 C8 0.27(14) . . . . ?
C1 C2 C9 C10 28.67(19) . . . . ?
C1 C2 C9 C13 -146.10(13) . . . . ?
C1 C12 N2 C11 -9.1(2) . . . . ?
C2 C1 C12 N2 -31.1(2) . . . . ?
C2 C1 N1 C8 1.69(15) . . . . ?
C2 C3 C4 C5 179.02(14) . . . . ?
C2 C3 C8 C7 -179.80(12) . . . . ?
C2 C3 C8 N1 0.73(14) . . . . ?
C2 C9 C10 C11 4.6(2) . . . . ?
C2 C9 C13 C14 -133.49(15) . . . . ?
C2 C9 C13 C18 49.43(19) . . . . ?
C3 C2 C9 C10 -159.18(13) . . . . ?
C3 C2 C9 C13 26.05(19) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C3 C8 N1 C1 -1.49(15) . . . . ?
C4 C3 C8 C7 -0.8(2) . . . . ?
C4 C3 C8 N1 179.72(12) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C7 C8 C3 0.6(2) . . . . ?
C6 C7 C8 N1 179.91(14) . . . . ?
C7 C8 N1 C1 179.10(14) . . . . ?
C8 C3 C4 C5 0.4(2) . . . . ?
C9 C2 C3 C4 8.3(2) . . . . ?
C9 C2 C3 C8 -172.92(12) . . . . ?
C9 C10 C11 C19 -176.92(13) . . . . ?
C9 C10 C11 C25 62.31(17) . . . . ?
C9 C10 C11 N2 -62.63(17) . . . . ?
C9 C13 C14 C15 -177.11(18) . . . . ?
C9 C13 C18 C17 176.16(16) . . . . ?
C10 C9 C13 C14 51.5(2) . . . . ?
C10 C9 C13 C18 -125.54(15) . . . . ?
C10 C11 C19 C20 78.79(15) . . . . ?
C10 C11 C19 C24 -97.66(15) . . . . ?
C10 C11 C25 C26 25.88(17) . . . . ?
C10 C11 C25 C30 -160.84(12) . . . . ?
C10 C11 N2 C12 63.11(16) . . . . ?
C11 C19 C20 C21 -177.13(14) . . . . ?
C11 C19 C24 C23 176.69(14) . . . . ?
C11 C25 C26 C27 171.77(13) . . . . ?
C11 C25 C30 C29 -172.17(14) . . . . ?
C12 C1 C2 C3 -171.76(13) . . . . ?
C12 C1 C2 C9 1.9(2) . . . . ?
C12 C1 N1 C8 172.88(12) . . . . ?
C13 C9 C10 C11 179.43(12) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C14 C13 C18 C17 -1.0(2) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C17 C18 C13 1.0(3) . . . . ?
C18 C13 C14 C15 0.0(3) . . . . ?
C19 C11 C25 C26 -93.27(15) . . . . ?
C19 C11 C25 C30 80.01(15) . . . . ?
C19 C11 N2 C12 177.85(12) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C19 C24 C23 0.2(2) . . . . ?
C20 C21 C22 C23 1.0(3) . . . . ?
C21 C22 C23 C24 -1.3(3) . . . . ?
C22 C23 C24 C19 0.7(3) . . . . ?
C24 C19 C20 C21 -0.5(2) . . . . ?
C25 C11 C19 C20 -157.27(12) . . . . ?
C25 C11 C19 C24 26.28(17) . . . . ?
C25 C11 N2 C12 -64.16(15) . . . . ?
C25 C26 C27 C28 0.5(2) . . . . ?
C26 C25 C30 C29 1.4(2) . . . . ?
C26 C27 C28 C29 1.0(3) . . . . ?
C27 C28 C29 C30 -1.2(3) . . . . ?
C28 C29 C30 C25 0.0(3) . . . . ?
C30 C25 C26 C27 -1.6(2) . . . . ?
N1 C1 C2 C3 -1.18(14) . . . . ?
N1 C1 C2 C9 172.53(11) . . . . ?
N1 C1 C12 N2 159.47(14) . . . . ?
N2 C11 C19 C20 -38.71(15) . . . . ?
N2 C11 C19 C24 144.84(13) . . . . ?
N2 C11 C25 C26 150.98(12) . . . . ?
N2 C11 C25 C30 -35.74(16) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 0.000 0.500 213.5 9.3 ?
2 0.500 0.500 0.000 213.5 9.3 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
