# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_220715_dmbnimd_mutoh
_database_code_depnum_ccdc_archive 'CCDC 2214825'
loop_
_audit_author_name
_audit_author_address
'Katsuya Mutoh'
;Aoyama Gakuin University
Japan
;
_audit_update_record             
;
2023-01-20 deposited with the CCDC.	2023-02-08 downloaded from the CCDC.
;
_audit_creation_date             2023-01-17
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2023.01.17 svn.r1b7d262c for OlexSys, GUI svn.r6444)
;
_chemical_formula_moiety         'C52 H36 N4'
_chemical_formula_sum            'C52 H36 N4'
_chemical_formula_weight         716.892
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.6158(3)
_cell_length_b                   25.7155(8)
_cell_length_c                   12.4043(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.105(3)
_cell_angle_gamma                90
_cell_volume                     3695.73(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7640
_cell_measurement_temperature    104(7)
_cell_measurement_theta_max      29.6100
_cell_measurement_theta_min      2.0990
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       plate
_exptl_crystal_F_000             1504.822
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.1071
_diffrn_reflns_Laue_measured_fraction_full 0.9949
_diffrn_reflns_Laue_measured_fraction_max 0.9934
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            39620
_diffrn_reflns_point_group_measured_fraction_full 0.9949
_diffrn_reflns_point_group_measured_fraction_max 0.9934
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.28
_diffrn_ambient_temperature      104(7)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.9949
_diffrn_measured_fraction_theta_max 0.9934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     61.00  87.00   0.50  257.17    --   20.00  54.00 150.00   52
  2  ω    -72.00 110.00   0.50  257.17    --   20.00  54.00 -90.00  364
  3  ω    -68.00 -36.00   0.50  257.17    --   20.00  54.00 -30.00   64
  4  ω     13.00  39.00   0.50  257.17    --   20.00  54.00 -30.00   52
  5  ω    -74.00  61.00   0.50  257.17    --   20.00  54.00-150.00  270
  6  ω    -67.00  28.00   0.50  257.17    --   20.00  54.00-120.00  190
  7  ω    -65.00 -38.00   0.50  257.17    --   20.00  54.00 -60.00   54
  8  ω    -68.00 -41.00   0.50  257.17    --   20.00  54.00   0.00   54
  9  ω      1.00  26.00   0.50  257.17    --   20.00  54.00   0.00   50
 10  ω    -59.00 -32.00   0.50  257.17    --   20.00  54.00 150.00   54
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -14
_reflns_limit_k_max              31
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              -9
_reflns_number_gt                4668
_reflns_number_total             7227
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.4759
_refine_diff_density_min         -0.4254
_refine_diff_density_rms         0.0982
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             8.9153
_refine_ls_extinction_coef       0.0013
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0332
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    63
_refine_ls_number_parameters     523
_refine_ls_number_reflns         7227
_refine_ls_number_restraints     189
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.0190
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.6253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1114
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C3AA, C4AA, C2AA, C3, C0AA, C1AA
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C3AA, C4AA, C1AA, C0AA, C3, C2AA
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C28(H28), C53(H53), C54(H54), C52(H52), C50(H50), C27(H27), C26(H26),
 C31(H31), C25(H25), C51(H51), C7(H7), C24(H24), C30(H30), C18(H18), C22(H22),
 C21(H21), C20(H20), C33(H33), C34(H34), C19(H19), C1AA(H1AA), C3(H3),
 C3AA(H3AA), C4AA(H4AA), C2AA(H2AA)
3.b Idealised Me refined as rotating group:
 C55(H55a,H55b,H55c), C56(H56a,H56b,H56c)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
N16 N 0.49311(13) 0.32924(6) 0.33679(12) 0.0202(4) Uani 1.000000 . U .
N40 N 0.39477(13) 0.32957(6) 0.54016(12) 0.0210(4) Uani 1.000000 . U .
N3 N 0.31202(13) 0.35059(6) 0.28434(12) 0.0223(4) Uani 1.000000 . U .
N42 N 0.53573(13) 0.33986(6) 0.68151(12) 0.0227(4) Uani 1.000000 . U .
C41 C 0.51035(16) 0.32333(7) 0.57445(15) 0.0193(4) Uani 1.000000 . U .
C4 C 0.38380(16) 0.31266(7) 0.31368(15) 0.0208(4) Uani 1.000000 . U .
C28 C 0.20447(17) 0.44958(8) 0.26496(15) 0.0239(5) Uani 1.000000 . U .
H28 H 0.15991(17) 0.41868(8) 0.26727(15) 0.0286(5) Uiso 1.000000 R . .
C23 C 0.32514(16) 0.44645(7) 0.27484(15) 0.0213(4) Uani 1.000000 . U .
C14 C 0.48182(16) 0.24200(7) 0.39147(15) 0.0203(4) Uani 1.000000 . U .
C53 C 0.05259(17) 0.39282(8) 0.69820(17) 0.0259(5) Uani 1.000000 . U .
H53 H 0.01167(17) 0.39703(8) 0.76124(17) 0.0311(6) Uiso 1.000000 R . .
C49 C 0.22687(16) 0.36855(7) 0.61563(15) 0.0214(4) Uani 1.000000 . U .
C39 C 0.34756(16) 0.35183(7) 0.62197(15) 0.0205(4) Uani 1.000000 . U .
C54 C 0.16487(16) 0.37473(8) 0.70703(16) 0.0242(5) Uani 1.000000 . U .
H54 H 0.20033(16) 0.36640(8) 0.77626(16) 0.0290(5) Uiso 1.000000 R . .
C5 C 0.37604(16) 0.25877(7) 0.34318(15) 0.0219(4) Uani 1.000000 . U .
C2 C 0.37986(16) 0.39510(7) 0.29373(15) 0.0212(4) Uani 1.000000 . U .
C52 C -0.00056(17) 0.40483(8) 0.59770(17) 0.0270(5) Uani 1.000000 . U .
H52 H -0.07721(17) 0.41795(8) 0.59167(17) 0.0324(6) Uiso 1.000000 R . .
C37 C 0.67539(16) 0.28301(7) 0.32556(16) 0.0218(4) Uani 1.000000 . U .
C13 C 0.49197(17) 0.19009(7) 0.43556(15) 0.0232(4) Uani 1.000000 . U .
C8 C 0.38729(17) 0.15957(8) 0.42782(15) 0.0246(4) Uani 1.000000 . U .
C17 C 0.59893(16) 0.41470(7) 0.34987(15) 0.0210(4) Uani 1.000000 . U .
C38 C 0.43748(16) 0.35749(7) 0.71206(15) 0.0223(4) Uani 1.000000 . U .
C12 C 0.59405(17) 0.16551(8) 0.48658(16) 0.0263(5) Uani 1.000000 . U .
C50 C 0.17146(17) 0.37947(8) 0.51412(16) 0.0247(5) Uani 1.000000 . U .
H50 H 0.21136(17) 0.37441(8) 0.45071(16) 0.0297(5) Uiso 1.000000 R . .
C29 C 0.59656(16) 0.30882(7) 0.50993(15) 0.0208(4) Uani 1.000000 . U .
C15 C 0.56918(16) 0.28936(7) 0.39291(15) 0.0213(4) Uani 1.000000 . U .
C27 C 0.14945(18) 0.49696(8) 0.25191(16) 0.0273(5) Uani 1.000000 . U .
H27 H 0.06752(18) 0.49845(8) 0.24583(16) 0.0327(6) Uiso 1.000000 R . .
C1 C 0.49332(16) 0.38290(7) 0.32777(15) 0.0212(4) Uani 1.000000 . U .
C6 C 0.27685(18) 0.22710(8) 0.33170(16) 0.0249(5) Uani 1.000000 . U .
H6 H 0.2057(16) 0.2418(7) 0.2960(16) 0.0298(6) Uiso 1.000000 R . .
C26 C 0.21308(17) 0.54227(8) 0.24764(16) 0.0276(5) Uani 1.000000 . U .
H26 H 0.17502(17) 0.57488(8) 0.23943(16) 0.0332(6) Uiso 1.000000 R . .
C32 C 0.78503(17) 0.29710(7) 0.37197(16) 0.0242(4) Uani 1.000000 . U .
C31 C 0.80135(17) 0.31300(8) 0.48378(16) 0.0262(5) Uani 1.000000 . U .
H31 H 0.87735(17) 0.32059(8) 0.51294(16) 0.0314(6) Uiso 1.000000 R . .
C25 C 0.33164(17) 0.53993(8) 0.25532(16) 0.0271(5) Uani 1.000000 . U .
H25 H 0.37544(17) 0.57099(8) 0.25143(16) 0.0326(6) Uiso 1.000000 R . .
C51 C 0.05948(17) 0.39750(8) 0.50561(17) 0.0278(5) Uani 1.000000 . U .
H51 H 0.02292(17) 0.40500(8) 0.43639(17) 0.0333(6) Uiso 1.000000 R . .
C7 C 0.28438(17) 0.17853(8) 0.37438(16) 0.0265(5) Uani 1.000000 . U .
H7 H 0.21838(17) 0.15662(8) 0.36811(16) 0.0318(6) Uiso 1.000000 R . .
C36 C 0.66467(17) 0.26817(7) 0.21548(16) 0.0244(4) Uani 1.000000 . U .
C24 C 0.38768(17) 0.49250(7) 0.26870(16) 0.0245(5) Uani 1.000000 . U .
H24 H 0.46964(17) 0.49138(7) 0.27374(16) 0.0294(5) Uiso 1.000000 R . .
C30 C 0.71390(16) 0.31751(8) 0.54819(16) 0.0243(5) Uani 1.000000 . U .
H30 H 0.73059(16) 0.32681(8) 0.62177(16) 0.0292(5) Uiso 1.000000 R . .
C18 C 0.68871(17) 0.41300(8) 0.28121(16) 0.0260(5) Uani 1.000000 . U .
H18 H 0.68320(17) 0.39042(8) 0.22044(16) 0.0312(6) Uiso 1.000000 R . .
C11 C 0.5852(2) 0.11576(8) 0.52691(17) 0.0324(5) Uani 1.000000 . U .
H11 H 0.6552(18) 0.1014(8) 0.5591(17) 0.0388(6) Uiso 1.000000 R . .
C22 C 0.60984(17) 0.44770(8) 0.43940(16) 0.0265(5) Uani 1.000000 . U .
H22 H 0.55028(17) 0.44887(8) 0.48798(16) 0.0318(6) Uiso 1.000000 R . .
C9 C 0.3851(2) 0.10921(8) 0.47458(17) 0.0307(5) Uani 1.000000 . U .
H9 H 0.3092(18) 0.0906(8) 0.4733(16) 0.0368(6) Uiso 1.000000 R . .
C21 C 0.70656(18) 0.47872(8) 0.45805(17) 0.0304(5) Uani 1.000000 . U .
H21 H 0.71241(18) 0.50138(8) 0.51868(17) 0.0364(6) Uiso 1.000000 R . .
C35 C 0.76304(19) 0.26868(8) 0.15715(18) 0.0298(5) Uani 1.000000 . U .
H35 H 0.7557(16) 0.2587(8) 0.0799(18) 0.0357(6) Uiso 1.000000 R . .
C10 C 0.4824(2) 0.08755(9) 0.52283(18) 0.0355(5) Uani 1.000000 . U .
H10 H 0.4796(17) 0.0506(9) 0.5521(17) 0.0426(7) Uiso 1.000000 R . .
C20 C 0.79500(18) 0.47691(8) 0.38876(18) 0.0315(5) Uani 1.000000 . U .
H20 H 0.86133(18) 0.49822(8) 0.40179(18) 0.0378(6) Uiso 1.000000 R . .
C33 C 0.88162(18) 0.29637(8) 0.31082(17) 0.0302(5) Uani 1.000000 . U .
H33 H 0.95533(18) 0.30534(8) 0.34369(17) 0.0363(6) Uiso 1.000000 R . .
C55 C 0.55271(17) 0.25144(8) 0.15455(16) 0.0303(5) Uani 1.000000 . U .
H55a H 0.5206(6) 0.2215(3) 0.1910(6) 0.0455(8) Uiso 1.000000 GR . .
H55b H 0.4974(4) 0.28025(18) 0.1528(9) 0.0455(8) Uiso 1.000000 GR . .
H55c H 0.5679(3) 0.2418(5) 0.0805(3) 0.0455(8) Uiso 1.000000 GR . .
C34 C 0.87048(19) 0.28273(8) 0.20326(18) 0.0328(5) Uani 1.000000 . U .
H34 H 0.93573(19) 0.28296(8) 0.16126(18) 0.0394(6) Uiso 1.000000 R . .
C19 C 0.78605(18) 0.44384(8) 0.30043(18) 0.0321(5) Uani 1.000000 . U .
H19 H 0.84661(18) 0.44226(8) 0.25296(18) 0.0385(6) Uiso 1.000000 R . .
C56 C 0.70997(17) 0.19029(8) 0.49908(18) 0.0338(5) Uani 1.000000 . U .
H56a H 0.7320(5) 0.2022(5) 0.4284(2) 0.0506(8) Uiso 1.000000 GR . .
H56b H 0.7076(3) 0.2200(3) 0.5482(8) 0.0506(8) Uiso 1.000000 GR . .
H56c H 0.7667(3) 0.16494(17) 0.5289(10) 0.0506(8) Uiso 1.000000 GR . .
C0AA C 0.43097(17) 0.38205(8) 0.81887(16) 0.0264(5) Uani 1.000000 . U 1
C1AA C 0.48585(17) 0.35812(9) 0.90988(16) 0.0345(5) Uani 1.000000 . U 1
H1AA H 0.51981(17) 0.32476(9) 0.90350(16) 0.0414(7) Uiso 1.000000 R . 1
C3 C 0.37959(18) 0.43039(9) 0.82931(19) 0.0360(5) Uani 1.000000 . U 1
H3 H 0.34127(18) 0.44670(9) 0.76807(19) 0.0432(6) Uiso 1.000000 R . 1
C3AA C 0.4409(3) 0.43073(12) 1.0182(2) 0.0619(8) Uani 1.000000 . U 1
H3AA H 0.4452(3) 0.44767(12) 1.0864(2) 0.0742(10) Uiso 1.000000 R . 1
C4AA C 0.4909(2) 0.38274(12) 1.00871(19) 0.0522(7) Uani 1.000000 . U 1
H4AA H 0.5288(2) 0.36651(12) 1.07022(19) 0.0627(8) Uiso 1.000000 R . 1
C2AA C 0.3843(2) 0.45486(10) 0.9293(2) 0.0519(7) Uani 1.000000 . U 1
H2AA H 0.3490(2) 0.48786(10) 0.9369(2) 0.0622(8) Uiso 1.000000 R . 1


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
N16 C4 1.351(2) . ?
N16 C15 1.493(2) . ?
N16 C1 1.384(2) . ?
N40 C41 1.388(2) . ?
N40 C39 1.318(2) . ?
N3 C4 1.317(2) . ?
N3 C2 1.390(2) . ?
N42 C41 1.405(2) . ?
N42 C38 1.309(2) . ?
C41 C29 1.377(3) . ?
C4 C5 1.438(3) . ?
C28 H28 0.9500 . ?
C28 C23 1.401(3) . ?
C28 C27 1.380(3) . ?
C23 C2 1.477(3) . ?
C23 C24 1.394(3) . ?
C14 C5 1.396(3) . ?
C14 C13 1.444(3) . ?
C14 C15 1.584(3) . ?
C53 H53 0.9500 . ?
C53 C54 1.382(3) . ?
C53 C52 1.386(3) . ?
C49 C39 1.463(3) . ?
C49 C54 1.395(3) . ?
C49 C50 1.401(3) . ?
C39 C38 1.481(3) . ?
C54 H54 0.9500 . ?
C5 C6 1.410(3) . ?
C2 C1 1.391(3) . ?
C52 H52 0.9500 . ?
C52 C51 1.393(3) . ?
C37 C15 1.547(3) . ?
C37 C32 1.407(3) . ?
C37 C36 1.415(3) . ?
C13 C8 1.445(3) . ?
C13 C12 1.449(3) . ?
C8 C7 1.412(3) . ?
C8 C9 1.420(3) . ?
C17 C1 1.483(3) . ?
C17 C18 1.394(3) . ?
C17 C22 1.396(3) . ?
C38 C0AA 1.475(3) . ?
C12 C11 1.380(3) . ?
C12 C56 1.488(3) . ?
C50 H50 0.9500 . ?
C50 C51 1.378(3) . ?
C29 C15 1.547(3) . ?
C29 C30 1.428(3) . ?
C27 H27 0.9500 . ?
C27 C26 1.383(3) . ?
C6 H6 0.984(19) . ?
C6 C7 1.357(3) . ?
C26 H26 0.9500 . ?
C26 C25 1.375(3) . ?
C32 C31 1.445(3) . ?
C32 C33 1.399(3) . ?
C31 H31 0.9500 . ?
C31 C30 1.342(3) . ?
C25 H25 0.9500 . ?
C25 C24 1.387(3) . ?
C51 H51 0.9500 . ?
C7 H7 0.9500 . ?
C36 C35 1.396(3) . ?
C36 C55 1.519(3) . ?
C24 H24 0.9500 . ?
C30 H30 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.388(3) . ?
C11 H11 0.95(2) . ?
C11 C10 1.394(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.384(3) . ?
C9 H9 1.00(2) . ?
C9 C10 1.360(3) . ?
C21 H21 0.9500 . ?
C21 C20 1.387(3) . ?
C35 H35 0.99(2) . ?
C35 C34 1.383(3) . ?
C10 H10 1.02(2) . ?
C20 H20 0.9500 . ?
C20 C19 1.385(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.377(3) . ?
C55 H55a 0.9800 . ?
C55 H55b 0.9800 . ?
C55 H55c 0.9800 . ?
C34 H34 0.9500 . ?
C19 H19 0.9500 . ?
C56 H56a 0.9800 . ?
C56 H56b 0.9800 . ?
C56 H56c 0.9800 . ?
C0AA C1AA 1.399(3) . ?
C0AA C3 1.389(3) . ?
C1AA H1AA 0.9500 . ?
C1AA C4AA 1.377(3) . ?
C3 H3 0.9500 . ?
C3 C2AA 1.389(3) . ?
C3AA H3AA 0.9500 . ?
C3AA C4AA 1.372(4) . ?
C3AA C2AA 1.389(4) . ?
C4AA H4AA 0.9500 . ?
C2AA H2AA 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
C15 N16 C4 113.46(15) . . ?
C1 N16 C4 107.73(15) . . ?
C1 N16 C15 135.89(15) . . ?
C39 N40 C41 105.12(15) . . ?
C2 N3 C4 104.04(15) . . ?
C38 N42 C41 104.48(15) . . ?
N42 C41 N40 112.78(16) . . ?
C29 C41 N40 125.50(17) . . ?
C29 C41 N42 121.26(16) . . ?
N3 C4 N16 113.06(17) . . ?
C5 C4 N16 108.99(16) . . ?
C5 C4 N3 137.22(18) . . ?
C23 C28 H28 119.56(11) . . ?
C27 C28 H28 119.56(12) . . ?
C27 C28 C23 120.88(19) . . ?
C2 C23 C28 118.81(17) . . ?
C24 C23 C28 117.94(18) . . ?
C24 C23 C2 123.23(17) . . ?
C13 C14 C5 119.56(17) . . ?
C15 C14 C5 108.10(16) . . ?
C15 C14 C13 132.17(16) . . ?
C54 C53 H53 119.88(12) . . ?
C52 C53 H53 119.88(12) . . ?
C52 C53 C54 120.24(19) . . ?
C54 C49 C39 122.56(17) . . ?
C50 C49 C39 118.95(17) . . ?
C50 C49 C54 118.48(18) . . ?
C49 C39 N40 122.41(17) . . ?
C38 C39 N40 108.29(16) . . ?
C38 C39 C49 129.26(17) . . ?
C49 C54 C53 120.88(18) . . ?
H54 C54 C53 119.56(12) . . ?
H54 C54 C49 119.56(11) . . ?
C14 C5 C4 109.73(17) . . ?
C6 C5 C4 126.63(17) . . ?
C6 C5 C14 123.56(18) . . ?
C23 C2 N3 119.21(16) . . ?
C1 C2 N3 111.04(16) . . ?
C1 C2 C23 129.61(18) . . ?
H52 C52 C53 120.31(12) . . ?
C51 C52 C53 119.37(18) . . ?
C51 C52 H52 120.31(11) . . ?
C32 C37 C15 119.03(17) . . ?
C36 C37 C15 122.08(17) . . ?
C36 C37 C32 118.62(18) . . ?
C8 C13 C14 115.57(17) . . ?
C12 C13 C14 127.65(18) . . ?
C12 C13 C8 116.78(17) . . ?
C7 C8 C13 121.60(18) . . ?
C9 C8 C13 120.53(18) . . ?
C9 C8 C7 117.87(19) . . ?
C18 C17 C1 120.99(17) . . ?
C22 C17 C1 120.59(18) . . ?
C22 C17 C18 118.42(18) . . ?
C39 C38 N42 109.26(16) . . ?
C0AA C38 N42 120.68(16) . . ?
C0AA C38 C39 129.89(18) . . ?
C11 C12 C13 118.86(19) . . ?
C56 C12 C13 124.40(18) . . ?
C56 C12 C11 116.74(18) . . ?
H50 C50 C49 119.77(12) . . ?
C51 C50 C49 120.45(19) . . ?
C51 C50 H50 119.77(12) . . ?
C15 C29 C41 121.58(16) . . ?
C30 C29 C41 118.73(17) . . ?
C30 C29 C15 119.31(17) . . ?
C14 C15 N16 99.53(13) . . ?
C37 C15 N16 106.79(15) . . ?
C37 C15 C14 116.58(15) . . ?
C29 C15 N16 106.88(14) . . ?
C29 C15 C14 110.35(15) . . ?
C29 C15 C37 114.99(15) . . ?
H27 C27 C28 119.87(12) . . ?
C26 C27 C28 120.27(19) . . ?
C26 C27 H27 119.87(12) . . ?
C2 C1 N16 104.02(16) . . ?
C17 C1 N16 122.73(16) . . ?
C17 C1 C2 133.23(17) . . ?
H6 C6 C5 118.5(11) . . ?
C7 C6 C5 117.58(19) . . ?
C7 C6 H6 123.9(11) . . ?
H26 C26 C27 120.13(12) . . ?
C25 C26 C27 119.73(19) . . ?
C25 C26 H26 120.13(12) . . ?
C31 C32 C37 121.21(18) . . ?
C33 C32 C37 120.82(18) . . ?
C33 C32 C31 117.97(18) . . ?
H31 C31 C32 118.56(11) . . ?
C30 C31 C32 122.89(18) . . ?
C30 C31 H31 118.56(12) . . ?
H25 C25 C26 119.80(12) . . ?
C24 C25 C26 120.39(19) . . ?
C24 C25 H25 119.80(12) . . ?
C50 C51 C52 120.53(19) . . ?
H51 C51 C52 119.74(11) . . ?
H51 C51 C50 119.74(12) . . ?
C6 C7 C8 121.99(19) . . ?
H7 C7 C8 119.00(12) . . ?
H7 C7 C6 119.00(12) . . ?
C35 C36 C37 118.63(19) . . ?
C55 C36 C37 124.74(18) . . ?
C55 C36 C35 116.63(18) . . ?
C25 C24 C23 120.77(18) . . ?
H24 C24 C23 119.62(11) . . ?
H24 C24 C25 119.62(12) . . ?
C31 C30 C29 122.26(18) . . ?
H30 C30 C29 118.87(11) . . ?
H30 C30 C31 118.87(12) . . ?
H18 C18 C17 119.56(11) . . ?
C19 C18 C17 120.88(19) . . ?
C19 C18 H18 119.56(13) . . ?
H11 C11 C12 115.3(13) . . ?
C10 C11 C12 123.7(2) . . ?
C10 C11 H11 121.0(13) . . ?
H22 C22 C17 119.68(12) . . ?
C21 C22 C17 120.6(2) . . ?
C21 C22 H22 119.68(13) . . ?
H9 C9 C8 118.0(11) . . ?
C10 C9 C8 121.0(2) . . ?
C10 C9 H9 120.9(11) . . ?
H21 C21 C22 119.81(13) . . ?
C20 C21 C22 120.4(2) . . ?
C20 C21 H21 119.81(12) . . ?
H35 C35 C36 118.8(12) . . ?
C34 C35 C36 122.4(2) . . ?
C34 C35 H35 118.8(12) . . ?
C9 C10 C11 119.0(2) . . ?
H10 C10 C11 121.5(12) . . ?
H10 C10 C9 119.4(12) . . ?
H20 C20 C21 120.20(12) . . ?
C19 C20 C21 119.6(2) . . ?
C19 C20 H20 120.20(13) . . ?
H33 C33 C32 119.82(12) . . ?
C34 C33 C32 120.4(2) . . ?
C34 C33 H33 119.82(13) . . ?
H55a C55 C36 109.5 . . ?
H55b C55 C36 109.5 . . ?
H55b C55 H55a 109.5 . . ?
H55c C55 C36 109.5 . . ?
H55c C55 H55a 109.5 . . ?
H55c C55 H55b 109.5 . . ?
C33 C34 C35 119.1(2) . . ?
H34 C34 C35 120.43(13) . . ?
H34 C34 C33 120.43(13) . . ?
C20 C19 C18 120.1(2) . . ?
H19 C19 C18 119.97(13) . . ?
H19 C19 C20 119.97(13) . . ?
H56a C56 C12 109.5 . . ?
H56b C56 C12 109.5 . . ?
H56b C56 H56a 109.5 . . ?
H56c C56 C12 109.5 . . ?
H56c C56 H56a 109.5 . . ?
H56c C56 H56b 109.5 . . ?
C1AA C0AA C38 119.14(19) . . ?
C3 C0AA C38 121.14(19) . . ?
C3 C0AA C1AA 119.5(2) . . ?
H1AA C1AA C0AA 119.87(13) . . ?
C4AA C1AA C0AA 120.3(2) . . ?
C4AA C1AA H1AA 119.87(17) . . ?
H3 C3 C0AA 120.02(13) . . ?
C2AA C3 C0AA 120.0(2) . . ?
C2AA C3 H3 120.02(16) . . ?
C4AA C3AA H3AA 119.57(16) . . ?
C2AA C3AA H3AA 119.57(16) . . ?
C2AA C3AA C4AA 120.9(2) . . ?
C3AA C4AA C1AA 119.9(3) . . ?
H4AA C4AA C1AA 120.05(17) . . ?
H4AA C4AA C3AA 120.05(16) . . ?
C3AA C2AA C3 119.5(3) . . ?
H2AA C2AA C3 120.25(16) . . ?
H2AA C2AA C3AA 120.25(16) . . ?

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
N16 C4 N3 C2 -2.56(18) . . . . ?
N16 C4 C5 C14 3.32(17) . . . . ?
N16 C4 C5 C6 -179.81(15) . . . . ?
N16 C15 C14 C5 -1.74(15) . . . . ?
N16 C15 C14 C13 -176.93(13) . . . . ?
N16 C15 C37 C32 115.60(15) . . . . ?
N16 C15 C37 C36 -58.29(17) . . . . ?
N16 C15 C29 C41 52.37(17) . . . . ?
N16 C15 C29 C30 -120.55(15) . . . . ?
N16 C1 C2 N3 1.17(16) . . . . ?
N16 C1 C2 C23 176.83(13) . . . . ?
N16 C1 C17 C18 69.3(2) . . . . ?
N16 C1 C17 C22 -111.63(19) . . . . ?
N40 C41 N42 C38 -1.69(18) . . . . ?
N40 C41 C29 C15 -9.8(2) . . . . ?
N40 C41 C29 C30 163.19(19) . . . . ?
N40 C39 C49 C54 156.79(18) . . . . ?
N40 C39 C49 C50 -24.0(2) . . . . ?
N40 C39 C38 N42 1.50(17) . . . . ?
N40 C39 C38 C0AA 176.70(15) . . . . ?
N3 C4 C5 C14 -165.7(2) . . . . ?
N3 C4 C5 C6 11.1(3) . . . . ?
N3 C2 C23 C28 10.0(2) . . . . ?
N3 C2 C23 C24 -171.48(17) . . . . ?
N3 C2 C1 C17 179.71(14) . . . . ?
N42 C41 C29 C15 178.55(16) . . . . ?
N42 C41 C29 C30 -8.5(2) . . . . ?
N42 C38 C39 C49 -176.25(15) . . . . ?
N42 C38 C0AA C1AA -45.8(2) . . . . ?
N42 C38 C0AA C3 128.92(19) . . . . ?
C41 C29 C15 C14 -54.91(19) . . . . ?
C41 C29 C15 C37 170.70(18) . . . . ?
C41 C29 C30 C31 -168.20(18) . . . . ?
C4 C5 C14 C13 175.14(15) . . . . ?
C4 C5 C14 C15 -0.76(17) . . . . ?
C4 C5 C6 C7 -173.5(2) . . . . ?
C28 C23 C2 C1 -165.34(17) . . . . ?
C28 C23 C24 C25 1.2(2) . . . . ?
C28 C27 C26 C25 0.7(2) . . . . ?
C23 C2 C1 C17 -4.6(3) . . . . ?
C23 C24 C25 C26 -0.1(2) . . . . ?
C14 C5 C6 C7 2.9(2) . . . . ?
C14 C13 C8 C7 3.8(2) . . . . ?
C14 C13 C8 C9 -175.95(17) . . . . ?
C14 C13 C12 C11 178.0(2) . . . . ?
C14 C13 C12 C56 -2.0(2) . . . . ?
C14 C15 C37 C32 -134.25(16) . . . . ?
C14 C15 C37 C36 51.86(19) . . . . ?
C14 C15 C29 C30 132.16(15) . . . . ?
C53 C54 C49 C39 177.09(17) . . . . ?
C53 C54 C49 C50 -2.1(2) . . . . ?
C53 C52 C51 C50 -1.3(2) . . . . ?
C49 C39 C38 C0AA -1.0(3) . . . . ?
C49 C50 C51 C52 -0.4(2) . . . . ?
C39 C38 C0AA C1AA 139.5(2) . . . . ?
C39 C38 C0AA C3 -45.8(2) . . . . ?
C5 C6 C7 C8 -0.5(2) . . . . ?
C2 C1 C17 C18 -109.0(2) . . . . ?
C2 C1 C17 C22 70.0(2) . . . . ?
C37 C15 C29 C30 -2.22(19) . . . . ?
C37 C32 C31 C30 -3.0(2) . . . . ?
C37 C32 C33 C34 1.2(2) . . . . ?
C37 C36 C35 C34 0.6(2) . . . . ?
C13 C8 C7 C6 -2.9(2) . . . . ?
C13 C8 C9 C10 -3.3(2) . . . . ?
C13 C12 C11 C10 -0.9(2) . . . . ?
C8 C9 C10 C11 0.6(2) . . . . ?
C17 C18 C19 C20 -0.0(2) . . . . ?
C17 C22 C21 C20 -0.9(2) . . . . ?
C38 C0AA C1AA C4AA 173.56(19) . . . . ?
C38 C0AA C3 C2AA -173.9(2) . . . . ?
C12 C11 C10 C9 1.5(3) . . . . ?
C29 C30 C31 C32 -2.5(2) . . . . ?
C27 C26 C25 C24 -0.8(2) . . . . ?
C32 C33 C34 C35 -1.4(2) . . . . ?
C36 C35 C34 C33 0.5(2) . . . . ?
C18 C19 C20 C21 0.4(2) . . . . ?
C22 C21 C20 C19 0.1(2) . . . . ?
C0AA C1AA C4AA C3AA 0.6(2) . . . . ?
C0AA C3 C2AA C3AA 0.3(2) . . . . ?
C1AA C4AA C3AA C2AA 0.5(3) . . . . ?
C3 C2AA C3AA C4AA -0.9(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_restr_U_rigid_atom_site_label_1
_restr_U_rigid_atom_site_label_2
_restr_U_rigid_target_weight_param
_restr_U_rigid_U_parallel
_restr_U_rigid_diff
N16 N3 0.0050 0.0214 -0.0024
N16 C4 0.0050 0.0213 0.0026
N16 C14 0.0050 0.0239 -0.0025
N16 C5 0.0050 0.0254 -0.0020
N16 C2 0.0050 0.0212 -0.0038
N16 C37 0.0050 0.0205 0.0002
N16 C17 0.0050 0.0230 -0.0000
N16 C29 0.0050 0.0169 -0.0012
N16 C15 0.0050 0.0188 0.0003
N16 C1 0.0050 0.0219 -0.0012
N40 N42 0.0050 0.0181 0.0014
N40 C41 0.0050 0.0196 0.0009
N40 C49 0.0050 0.0215 -0.0021
N40 C39 0.0050 0.0205 -0.0021
N40 C38 0.0050 0.0182 0.0003
N40 C29 0.0050 0.0221 -0.0027
N3 C4 0.0050 0.0229 -0.0012
N3 C23 0.0050 0.0250 0.0002
N3 C5 0.0050 0.0241 -0.0006
N3 C2 0.0050 0.0265 -0.0002
N3 C1 0.0050 0.0254 -0.0009
N42 C41 0.0050 0.0157 0.0011
N42 C39 0.0050 0.0219 -0.0008
N42 C38 0.0050 0.0241 -0.0009
N42 C29 0.0050 0.0197 -0.0027
N42 C0AA 0.0050 0.0216 -0.0006
C41 C39 0.0050 0.0240 0.0000
C41 C38 0.0050 0.0212 0.0000
C41 C29 0.0050 0.0238 -0.0001
C41 C15 0.0050 0.0197 -0.0001
C41 C30 0.0050 0.0236 -0.0022
C4 C14 0.0050 0.0244 0.0002
C4 C5 0.0050 0.0274 0.0037
C4 C2 0.0050 0.0271 0.0025
C4 C15 0.0050 0.0191 -0.0022
C4 C1 0.0050 0.0253 0.0005
C4 C6 0.0050 0.0287 -0.0015
C28 C23 0.0050 0.0265 0.0004
C28 C2 0.0050 0.0242 0.0028
C28 C27 0.0050 0.0250 0.0007
C28 C26 0.0050 0.0257 -0.0003
C28 C24 0.0050 0.0265 0.0011
C23 C2 0.0050 0.0233 -0.0016
C23 C27 0.0050 0.0220 0.0024
C23 C1 0.0050 0.0223 -0.0003
C23 C25 0.0050 0.0247 0.0002
C23 C24 0.0050 0.0282 -0.0005
C14 C5 0.0050 0.0233 -0.0006
C14 C37 0.0050 0.0247 -0.0004
C14 C13 0.0050 0.0249 0.0005
C14 C8 0.0050 0.0256 -0.0007
C14 C12 0.0050 0.0245 -0.0006
C14 C29 0.0050 0.0179 -0.0012
C14 C15 0.0050 0.0248 -0.0010
C14 C6 0.0050 0.0228 0.0004
C53 C49 0.0050 0.0228 0.0002
C53 C54 0.0050 0.0253 0.0012
C53 C52 0.0050 0.0285 -0.0018
C53 C51 0.0050 0.0235 0.0020
C49 C39 0.0050 0.0231 -0.0015
C49 C54 0.0050 0.0229 -0.0007
C49 C38 0.0050 0.0217 -0.0010
C49 C50 0.0050 0.0215 0.0000
C49 C51 0.0050 0.0217 0.0001
C39 C54 0.0050 0.0242 -0.0022
C39 C38 0.0050 0.0192 0.0001
C39 C50 0.0050 0.0225 -0.0012
C39 C0AA 0.0050 0.0176 0.0015
C54 C52 0.0050 0.0220 -0.0001
C54 C50 0.0050 0.0207 -0.0008
C5 C13 0.0050 0.0246 -0.0012
C5 C15 0.0050 0.0244 0.0011
C5 C6 0.0050 0.0259 0.0004
C5 C7 0.0050 0.0259 0.0019
C2 C17 0.0050 0.0231 0.0010
C2 C1 0.0050 0.0231 -0.0018
C2 C24 0.0050 0.0270 -0.0018
C52 C50 0.0050 0.0237 -0.0012
C52 C51 0.0050 0.0294 0.0019
C37 C29 0.0050 0.0212 -0.0005
C37 C15 0.0050 0.0232 -0.0021
C37 C32 0.0050 0.0275 -0.0007
C37 C31 0.0050 0.0230 0.0054
C37 C36 0.0050 0.0216 0.0017
C37 C35 0.0050 0.0215 -0.0010
C37 C33 0.0050 0.0258 -0.0004
C37 C55 0.0050 0.0244 0.0021
C13 C8 0.0050 0.0293 0.0017
C13 C12 0.0050 0.0273 0.0003
C13 C15 0.0050 0.0251 0.0024
C13 C7 0.0050 0.0271 0.0063
C13 C11 0.0050 0.0241 0.0013
C13 C9 0.0050 0.0265 0.0020
C13 C56 0.0050 0.0286 0.0033
C8 C12 0.0050 0.0319 -0.0008
C8 C6 0.0050 0.0287 0.0020
C8 C7 0.0050 0.0315 0.0003
C8 C9 0.0050 0.0272 -0.0014
C8 C10 0.0050 0.0274 0.0034
C17 C1 0.0050 0.0249 -0.0019
C17 C18 0.0050 0.0263 -0.0007
C17 C22 0.0050 0.0206 -0.0002
C17 C21 0.0050 0.0198 0.0026
C17 C19 0.0050 0.0262 0.0005
C38 C0AA 0.0050 0.0184 0.0016
C38 C1AA 0.0050 0.0191 -0.0013
C38 C3 0.0050 0.0255 -0.0042
C12 C11 0.0050 0.0287 -0.0024
C12 C10 0.0050 0.0321 0.0005
C12 C56 0.0050 0.0353 -0.0010
C50 C51 0.0050 0.0261 -0.0030
C29 C15 0.0050 0.0177 0.0005
C29 C31 0.0050 0.0218 0.0027
C29 C30 0.0050 0.0211 -0.0021
C15 C1 0.0050 0.0211 -0.0012
C15 C32 0.0050 0.0250 0.0002
C15 C36 0.0050 0.0206 0.0004
C15 C30 0.0050 0.0184 0.0005
C27 C26 0.0050 0.0340 0.0014
C27 C25 0.0050 0.0306 0.0007
C1 C18 0.0050 0.0282 -0.0020
C1 C22 0.0050 0.0227 -0.0042
C6 C7 0.0050 0.0321 -0.0017
C26 C25 0.0050 0.0318 -0.0012
C26 C24 0.0050 0.0231 0.0013
C32 C31 0.0050 0.0243 -0.0007
C32 C36 0.0050 0.0272 -0.0004
C32 C30 0.0050 0.0208 0.0014
C32 C33 0.0050 0.0237 -0.0030
C32 C34 0.0050 0.0213 0.0001
C31 C30 0.0050 0.0245 0.0007
C31 C33 0.0050 0.0277 -0.0016
C25 C24 0.0050 0.0258 0.0019
C7 C9 0.0050 0.0348 0.0022
C36 C35 0.0050 0.0287 -0.0030
C36 C55 0.0050 0.0333 -0.0007
C36 C34 0.0050 0.0333 0.0002
C18 C22 0.0050 0.0215 0.0011
C18 C20 0.0050 0.0234 -0.0003
C18 C19 0.0050 0.0286 -0.0021
C11 C9 0.0050 0.0351 0.0012
C11 C10 0.0050 0.0416 -0.0010
C11 C56 0.0050 0.0390 0.0003
C22 C21 0.0050 0.0279 0.0023
C22 C20 0.0050 0.0294 -0.0002
C9 C10 0.0050 0.0369 0.0001
C21 C20 0.0050 0.0395 0.0006
C21 C19 0.0050 0.0309 0.0016
C35 C33 0.0050 0.0333 0.0005
C35 C55 0.0050 0.0403 -0.0001
C35 C34 0.0050 0.0427 -0.0029
C20 C19 0.0050 0.0336 -0.0006
C33 C34 0.0050 0.0323 -0.0002
C0AA C1AA 0.0100 0.0337 0.0001
C0AA C1AA 0.0200 0.0337 0.0001
C0AA C1AA 0.0050 0.0337 0.0001
C0AA C3 0.0100 0.0419 -0.0017
C0AA C3 0.0200 0.0419 -0.0017
C0AA C3 0.0050 0.0419 -0.0017
C0AA C4AA 0.0200 0.0209 -0.0008
C0AA C4AA 0.0100 0.0209 -0.0008
C0AA C4AA 0.0050 0.0209 -0.0008
C0AA C2AA 0.0100 0.0275 0.0003
C0AA C2AA 0.0200 0.0275 0.0003
C0AA C2AA 0.0050 0.0275 0.0003
C1AA C3 0.0200 0.0559 -0.0001
C1AA C3 0.0050 0.0559 -0.0001
C1AA C3 0.0100 0.0559 -0.0001
C1AA C3AA 0.0200 0.0518 -0.0036
C1AA C3AA 0.0050 0.0518 -0.0036
C1AA C3AA 0.0100 0.0518 -0.0036
C1AA C4AA 0.0100 0.0274 0.0008
C1AA C4AA 0.0200 0.0274 0.0008
C1AA C4AA 0.0050 0.0274 0.0008
C3 C3AA 0.0200 0.0389 0.0014
C3 C3AA 0.0050 0.0389 0.0014
C3 C3AA 0.0100 0.0389 0.0014
C3 C2AA 0.0200 0.0278 -0.0030
C3 C2AA 0.0050 0.0278 -0.0030
C3 C2AA 0.0100 0.0278 -0.0030
C3AA C4AA 0.0100 0.1099 0.0084
C3AA C4AA 0.0200 0.1099 0.0084
C3AA C4AA 0.0050 0.1099 0.0084
C3AA C2AA 0.0200 0.1008 -0.0027
C3AA C2AA 0.0100 0.1008 -0.0027
C3AA C2AA 0.0050 0.1008 -0.0027
C4AA C2AA 0.0100 0.1000 0.0003
C4AA C2AA 0.0200 0.1000 0.0003
C4AA C2AA 0.0050 0.1000 0.0003

####################################################################### 
# 
# 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_moriyama_bnimd
_database_code_depnum_ccdc_archive 'CCDC 2231675'
loop_
_audit_author_name
_audit_author_address
'Jiro Abe'
;AOYAMA GAKUIN UNIVERSITY
Japan
;
_audit_update_record             
;
2022-12-20 deposited with the CCDC.	2023-02-08 downloaded from the CCDC.
;
_audit_creation_date             2022-12-20
_audit_creation_method           
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C50 H32 N4'
_chemical_formula_sum            'C50 H32 N4'
_chemical_formula_weight         688.79
_chemical_absolute_configuration unk
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.5250(5)
_cell_length_b                   14.4544(9)
_cell_length_c                   26.1380(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3598.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4731
_cell_measurement_temperature    106(8)
_cell_measurement_theta_max      29.1590
_cell_measurement_theta_min      2.1640
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull reddish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            19914
_diffrn_reflns_point_group_measured_fraction_full 0.878
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.559
_diffrn_reflns_theta_min         2.101
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      106(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     74.00 101.00   0.50    4.11    --   20.00  54.00   0.00   54
  2  ω    -60.00 -34.00   0.50    4.11    --   20.00  54.00 -90.00   52
  3  ω     -2.00 109.00   0.50    4.11    --   20.00  54.00 -90.00  222
  4  ω     15.00  61.00   0.50    4.11    --   20.00  54.00-180.00   92
  5  ω    -63.00 -38.00   0.50    4.11    --   20.00  54.00-150.00   50
  6  ω    -32.00  -7.00   0.50    4.11    --   20.00  54.00-150.00   50
  7  ω     68.00 110.00   0.50    4.11    --   20.00  54.00  90.00   84
  8  ω     -8.00  17.00   0.50    4.11    --   20.00  54.00   0.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0643341000
_diffrn_orient_matrix_UB_12      0.0176086000
_diffrn_orient_matrix_UB_13      -0.0095803000
_diffrn_orient_matrix_UB_21      -0.0239364000
_diffrn_orient_matrix_UB_22      0.0458032000
_diffrn_orient_matrix_UB_23      0.0044222000
_diffrn_orient_matrix_UB_31      0.0288472000
_diffrn_orient_matrix_UB_32      -0.0014142000
_diffrn_orient_matrix_UB_33      0.0249934000
_diffrn_oxdiff_digest_frames     
;
014dd102197204b48a85b7397dd82f2b72006543f41
;
_diffrn_oxdiff_digest_hkl        
;
01ac8ca16e75b432146d53ab9e6d8a4d1282d3
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.504
_reflns_Friedel_fraction_full    0.721
_reflns_Friedel_fraction_max     0.601
_reflns_number_gt                7186
_reflns_number_total             8837
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 2106 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         8837
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0500
_refine_ls_restrained_S_all      1.021
_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)+(0.0574P)²+0.5123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1176
_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:
 C48(H48), C44(H44), C42(H42), C21(H21), C27(H27), C13(H13), C20(H20),
 C18(H18), C22(H22), C53(H53), C52(H52), C46(H46), C54(H54), C19(H19), C7(H7),
 C26(H26), C41(H41), C12(H12), C29(H29), C24(H24), C10(H10), C47(H47), C50(H50),
  C25(H25), C45(H45), C9(H9), C30(H30), C38(H38), C39(H39), C51(H51), C8(H8),
 C40(H40)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C36 C -0.6796(2) -0.06502(16) -0.05921(8) 0.0183(4) Uani 1 1 d . . . . .
C48 C -0.6128(3) 0.05820(17) 0.00192(9) 0.0223(5) Uani 1 1 d . . . . .
H48 H -0.582336 0.093578 -0.025641 0.027 Uiso 1 1 calc R . . . .
N3 N -0.5117(2) 0.09167(13) -0.17185(7) 0.0175(4) Uani 1 1 d . . . . .
N35 N -0.6697(2) -0.01001(13) -0.09913(7) 0.0191(4) Uani 1 1 d . . . . .
C37 C -0.7111(2) -0.25039(16) -0.05072(8) 0.0187(5) Uani 1 1 d . . . . .
N33 N -0.7090(2) -0.16060(13) -0.12759(7) 0.0202(4) Uani 1 1 d . . . . .
C6 C -0.8700(2) 0.12508(17) -0.22209(9) 0.0218(5) Uani 1 1 d . . . . .
C44 C -0.7145(2) -0.08198(17) 0.03559(8) 0.0215(5) Uani 1 1 d . . . . .
H44 H -0.753247 -0.140324 0.030526 0.026 Uiso 1 1 calc R . . . .
C42 C -0.6084(3) -0.27685(18) -0.01586(9) 0.0250(5) Uani 1 1 d . . . . .
H42 H -0.539052 -0.235009 -0.006248 0.030 Uiso 1 1 calc R . . . .
C21 C 0.0055(3) 0.10152(18) -0.05892(10) 0.0273(5) Uani 1 1 d . . . . .
H21 H 0.091667 0.077243 -0.068914 0.033 Uiso 1 1 calc R . . . .
N16 N -0.4672(2) 0.19452(14) -0.11019(7) 0.0203(4) Uani 1 1 d . . . . .
C27 C -0.5085(3) -0.0073(2) -0.34504(9) 0.0278(6) Uani 1 1 d . . . . .
H27 H -0.502307 -0.058821 -0.366225 0.033 Uiso 1 1 calc R . . . .
C23 C -0.5660(2) 0.06042(17) -0.26285(8) 0.0183(4) Uani 1 1 d . . . . .
C5 C -0.7380(2) 0.12279(16) -0.19772(8) 0.0182(4) Uani 1 1 d . . . . .
C13 C -0.7924(3) 0.25838(17) -0.14633(9) 0.0252(5) Uani 1 1 d . . . . .
H13 H -0.765885 0.302033 -0.122044 0.030 Uiso 1 1 calc R . . . .
C28 C -0.5600(2) -0.01716(18) -0.29508(9) 0.0220(5) Uani 1 1 d . . . . .
C17 C -0.2376(2) 0.13372(16) -0.07805(8) 0.0186(5) Uani 1 1 d . . . . .
C14 C -0.6985(3) 0.18858(17) -0.16219(8) 0.0203(5) Uani 1 1 d . . . . .
C11 C -0.9644(3) 0.19661(19) -0.20622(10) 0.0262(5) Uani 1 1 d . . . . .
C20 C -0.0086(3) 0.14118(18) -0.01085(10) 0.0297(6) Uani 1 1 d . . . . .
H20 H 0.066945 0.142082 0.011690 0.036 Uiso 1 1 calc R . . . .
C18 C -0.2503(3) 0.17570(16) -0.02968(9) 0.0224(5) Uani 1 1 d . . . . .
H18 H -0.335761 0.201100 -0.019765 0.027 Uiso 1 1 calc R . . . .
C22 C -0.1076(3) 0.09776(17) -0.09212(9) 0.0230(5) Uani 1 1 d . . . . .
H22 H -0.096588 0.070899 -0.124200 0.028 Uiso 1 1 calc R . . . .
C2 C -0.3887(2) 0.06210(16) -0.14922(8) 0.0175(4) Uani 1 1 d . . . . .
C32 C -0.7033(2) -0.16096(16) -0.07784(8) 0.0191(5) Uani 1 1 d . . . . .
C34 C -0.6835(2) -0.06792(16) -0.14124(8) 0.0190(5) Uani 1 1 d . . . . .
C53 C -0.2207(3) -0.1391(2) -0.21806(11) 0.0410(8) Uani 1 1 d . . . . .
H53 H -0.193569 -0.155647 -0.250991 0.049 Uiso 1 1 calc R . . . .
C52 C -0.1991(3) -0.1997(2) -0.17809(11) 0.0392(7) Uani 1 1 d . . . . .
H52 H -0.155726 -0.256319 -0.183887 0.047 Uiso 1 1 calc R . . . .
C46 C -0.6452(3) 0.04017(18) 0.09280(9) 0.0276(6) Uani 1 1 d . . . . .
H46 H -0.635738 0.063082 0.125864 0.033 Uiso 1 1 calc R . . . .
C31 C -0.6582(2) -0.04553(16) -0.19164(8) 0.0184(5) Uani 1 1 d . . . . .
C54 C -0.2827(3) -0.0536(2) -0.20945(9) 0.0302(6) Uani 1 1 d . . . . .
H54 H -0.296964 -0.013162 -0.236642 0.036 Uiso 1 1 calc R . . . .
C19 C -0.1365(3) 0.17952(17) 0.00328(9) 0.0278(6) Uani 1 1 d . . . . .
H19 H -0.145863 0.207906 0.035029 0.033 Uiso 1 1 calc R . . . .
C1 C -0.3608(2) 0.12875(16) -0.11212(8) 0.0180(4) Uani 1 1 d . . . . .
C7 C -0.9119(3) 0.06362(19) -0.26157(10) 0.0268(5) Uani 1 1 d . . . . .
H7 H -0.852594 0.015768 -0.271509 0.032 Uiso 1 1 calc R . . . .
C26 C -0.4669(3) 0.0781(2) -0.36307(9) 0.0296(6) Uani 1 1 d . . . . .
H26 H -0.431733 0.083798 -0.396120 0.036 Uiso 1 1 calc R . . . .
C41 C -0.6088(3) -0.36593(19) 0.00476(9) 0.0293(6) Uani 1 1 d . . . . .
H41 H -0.538828 -0.383807 0.027512 0.035 Uiso 1 1 calc R . . . .
C12 C -0.9235(3) 0.26008(19) -0.16765(10) 0.0285(6) Uani 1 1 d . . . . .
H12 H -0.987692 0.304173 -0.156518 0.034 Uiso 1 1 calc R . . . .
C29 C -0.6109(3) -0.10581(18) -0.27702(9) 0.0265(5) Uani 1 1 d . . . . .
H29 H -0.610266 -0.156048 -0.299249 0.032 Uiso 1 1 calc R . . . .
C24 C -0.5265(2) 0.14607(18) -0.28153(9) 0.0223(5) Uani 1 1 d . . . . .
H24 H -0.532386 0.197923 -0.260576 0.027 Uiso 1 1 calc R . . . .
C10 C -1.0968(3) 0.2030(2) -0.23078(12) 0.0379(7) Uani 1 1 d . . . . .
H10 H -1.160650 0.247696 -0.220174 0.045 Uiso 1 1 calc R . . . .
C47 C -0.6023(3) 0.09322(18) 0.05124(9) 0.0266(5) Uani 1 1 d . . . . .
H47 H -0.566478 0.152316 0.056503 0.032 Uiso 1 1 calc R . . . .
C50 C -0.3045(3) -0.09104(17) -0.12056(9) 0.0258(5) Uani 1 1 d . . . . .
H50 H -0.333951 -0.075896 -0.087684 0.031 Uiso 1 1 calc R . . . .
C25 C -0.4774(3) 0.1552(2) -0.33195(9) 0.0283(6) Uani 1 1 d . . . . .
H25 H -0.451956 0.213112 -0.344421 0.034 Uiso 1 1 calc R . . . .
C45 C -0.7021(3) -0.04710(18) 0.08481(9) 0.0264(5) Uani 1 1 d . . . . .
H45 H -0.732060 -0.082242 0.112543 0.032 Uiso 1 1 calc R . . . .
C9 C -1.1320(3) 0.1446(2) -0.26968(14) 0.0455(8) Uani 1 1 d . . . . .
H9 H -1.218042 0.151239 -0.286098 0.055 Uiso 1 1 calc R . . . .
C4 C -0.6176(2) 0.05309(16) -0.20713(8) 0.0174(4) Uani 1 1 d . . . . .
C30 C -0.6590(3) -0.11766(17) -0.22911(9) 0.0244(5) Uani 1 1 d . . . . .
H30 H -0.694364 -0.175284 -0.219927 0.029 Uiso 1 1 calc R . . . .
C38 C -0.8159(3) -0.31349(17) -0.06435(9) 0.0233(5) Uani 1 1 d . . . . .
H38 H -0.884770 -0.296613 -0.087803 0.028 Uiso 1 1 calc R . . . .
C43 C -0.6691(2) -0.03002(16) -0.00665(8) 0.0192(5) Uani 1 1 d . . . . .
C39 C -0.8173(3) -0.40136(18) -0.04286(10) 0.0281(5) Uani 1 1 d . . . . .
H39 H -0.888146 -0.442764 -0.051478 0.034 Uiso 1 1 calc R . . . .
C51 C -0.2420(3) -0.17597(19) -0.12968(11) 0.0339(6) Uani 1 1 d . . . . .
H51 H -0.228970 -0.217269 -0.102810 0.041 Uiso 1 1 calc R . . . .
C15 C -0.5565(2) 0.16807(16) -0.14585(8) 0.0191(5) Uani 1 1 d . . . . .
C8 C -1.0393(3) 0.0744(2) -0.28511(12) 0.0373(7) Uani 1 1 d . . . . .
H8 H -1.064597 0.034905 -0.311611 0.045 Uiso 1 1 calc R . . . .
C49 C -0.3235(2) -0.02807(16) -0.16043(8) 0.0191(5) Uani 1 1 d . . . . .
C40 C -0.7137(3) -0.42764(18) -0.00871(9) 0.0298(6) Uani 1 1 d . . . . .
H40 H -0.714578 -0.486839 0.005217 0.036 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
C36 N35 1.315(3) . ?
C36 C32 1.487(3) . ?
C36 C43 1.468(3) . ?
C48 H48 0.9300 . ?
C48 C47 1.389(3) . ?
C48 C43 1.401(3) . ?
N3 C2 1.380(3) . ?
N3 C4 1.476(3) . ?
N3 C15 1.365(3) . ?
N35 C34 1.389(3) . ?
C37 C42 1.391(3) . ?
C37 C32 1.476(3) . ?
C37 C38 1.399(3) . ?
N33 C32 1.302(3) . ?
N33 C34 1.407(3) . ?
C6 C5 1.410(3) . ?
C6 C11 1.431(3) . ?
C6 C7 1.419(4) . ?
C44 H44 0.9300 . ?
C44 C45 1.387(3) . ?
C44 C43 1.404(3) . ?
C42 H42 0.9300 . ?
C42 C41 1.396(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.387(4) . ?
C21 C22 1.384(3) . ?
N16 C1 1.390(3) . ?
N16 C15 1.318(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.402(3) . ?
C27 C26 1.379(4) . ?
C23 C28 1.404(3) . ?
C23 C24 1.383(3) . ?
C23 C4 1.541(3) . ?
C5 C14 1.381(3) . ?
C5 C4 1.546(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.410(3) . ?
C13 C12 1.367(4) . ?
C28 C29 1.449(3) . ?
C17 C18 1.407(3) . ?
C17 C22 1.393(3) . ?
C17 C1 1.475(3) . ?
C14 C15 1.450(3) . ?
C11 C12 1.418(4) . ?
C11 C10 1.418(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.389(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(3) . ?
C22 H22 0.9300 . ?
C2 C1 1.392(3) . ?
C2 C49 1.473(3) . ?
C34 C31 1.378(3) . ?
C53 H53 0.9300 . ?
C53 C52 1.378(4) . ?
C53 C54 1.389(4) . ?
C52 H52 0.9300 . ?
C52 C51 1.373(4) . ?
C46 H46 0.9300 . ?
C46 C47 1.391(3) . ?
C46 C45 1.389(4) . ?
C31 C4 1.532(3) . ?
C31 C30 1.431(3) . ?
C54 H54 0.9300 . ?
C54 C49 1.389(3) . ?
C19 H19 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.369(4) . ?
C26 H26 0.9300 . ?
C26 C25 1.384(4) . ?
C41 H41 0.9300 . ?
C41 C40 1.385(4) . ?
C12 H12 0.9300 . ?
C29 H29 0.9300 . ?
C29 C30 1.344(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.405(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.363(4) . ?
C47 H47 0.9300 . ?
C50 H50 0.9300 . ?
C50 C51 1.385(4) . ?
C50 C49 1.395(3) . ?
C25 H25 0.9300 . ?
C45 H45 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.404(4) . ?
C30 H30 0.9300 . ?
C38 H38 0.9300 . ?
C38 C39 1.389(3) . ?
C39 H39 0.9300 . ?
C39 C40 1.383(4) . ?
C51 H51 0.9300 . ?
C8 H8 0.9300 . ?
C40 H40 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
N35 C36 C32 108.36(19) . . ?
N35 C36 C43 122.0(2) . . ?
C43 C36 C32 129.7(2) . . ?
C47 C48 H48 119.7 . . ?
C47 C48 C43 120.5(2) . . ?
C43 C48 H48 119.7 . . ?
C2 N3 C4 137.0(2) . . ?
C15 N3 C2 107.59(18) . . ?
C15 N3 C4 113.78(19) . . ?
C36 N35 C34 104.91(18) . . ?
C42 C37 C32 121.3(2) . . ?
C42 C37 C38 119.3(2) . . ?
C38 C37 C32 119.0(2) . . ?
C32 N33 C34 104.5(2) . . ?
C5 C6 C11 116.5(2) . . ?
C5 C6 C7 124.4(2) . . ?
C7 C6 C11 119.1(2) . . ?
C45 C44 H44 119.7 . . ?
C45 C44 C43 120.6(2) . . ?
C43 C44 H44 119.7 . . ?
C37 C42 H42 119.8 . . ?
C37 C42 C41 120.3(2) . . ?
C41 C42 H42 119.8 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C22 C21 C20 120.6(2) . . ?
C15 N16 C1 104.24(19) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C26 C27 C28 120.7(2) . . ?
C28 C23 C4 121.7(2) . . ?
C24 C23 C28 119.5(2) . . ?
C24 C23 C4 118.8(2) . . ?
C6 C5 C4 127.2(2) . . ?
C14 C5 C6 122.0(2) . . ?
C14 C5 C4 110.74(19) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C12 C13 C14 118.2(2) . . ?
C27 C28 C23 119.5(2) . . ?
C27 C28 C29 120.7(2) . . ?
C23 C28 C29 119.8(2) . . ?
C18 C17 C1 119.7(2) . . ?
C22 C17 C18 118.3(2) . . ?
C22 C17 C1 122.0(2) . . ?
C5 C14 C13 121.2(2) . . ?
C5 C14 C15 108.1(2) . . ?
C13 C14 C15 130.7(2) . . ?
C12 C11 C6 120.1(2) . . ?
C12 C11 C10 121.6(2) . . ?
C10 C11 C6 118.3(3) . . ?
C21 C20 H20 120.3 . . ?
C21 C20 C19 119.4(2) . . ?
C19 C20 H20 120.3 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.6(2) . . ?
C19 C18 H18 119.7 . . ?
C21 C22 C17 120.8(2) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
N3 C2 C1 104.23(19) . . ?
N3 C2 C49 123.1(2) . . ?
C1 C2 C49 132.1(2) . . ?
C37 C32 C36 131.9(2) . . ?
N33 C32 C36 109.2(2) . . ?
N33 C32 C37 118.8(2) . . ?
N35 C34 N33 112.90(18) . . ?
C31 C34 N35 126.8(2) . . ?
C31 C34 N33 119.7(2) . . ?
C52 C53 H53 119.8 . . ?
C52 C53 C54 120.4(3) . . ?
C54 C53 H53 119.8 . . ?
C53 C52 H52 120.1 . . ?
C51 C52 C53 119.7(3) . . ?
C51 C52 H52 120.1 . . ?
C47 C46 H46 120.1 . . ?
C45 C46 H46 120.1 . . ?
C45 C46 C47 119.9(2) . . ?
C34 C31 C4 121.0(2) . . ?
C34 C31 C30 118.9(2) . . ?
C30 C31 C4 119.91(19) . . ?
C53 C54 H54 119.8 . . ?
C53 C54 C49 120.3(2) . . ?
C49 C54 H54 119.8 . . ?
C20 C19 H19 119.8 . . ?
C18 C19 C20 120.3(2) . . ?
C18 C19 H19 119.8 . . ?
N16 C1 C17 121.6(2) . . ?
N16 C1 C2 111.08(19) . . ?
C2 C1 C17 127.3(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.9 . . ?
C27 C26 H26 120.0 . . ?
C27 C26 C25 120.0(2) . . ?
C25 C26 H26 120.0 . . ?
C42 C41 H41 120.1 . . ?
C40 C41 C42 119.9(2) . . ?
C40 C41 H41 120.1 . . ?
C13 C12 C11 121.9(2) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C28 C29 H29 119.0 . . ?
C30 C29 C28 122.0(2) . . ?
C30 C29 H29 119.0 . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.4(2) . . ?
C25 C24 H24 119.8 . . ?
C11 C10 H10 119.5 . . ?
C9 C10 C11 121.1(3) . . ?
C9 C10 H10 119.5 . . ?
C48 C47 C46 120.2(2) . . ?
C48 C47 H47 119.9 . . ?
C46 C47 H47 119.9 . . ?
C51 C50 H50 119.8 . . ?
C51 C50 C49 120.4(2) . . ?
C49 C50 H50 119.8 . . ?
C26 C25 C24 120.0(2) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C44 C45 C46 120.2(2) . . ?
C44 C45 H45 119.9 . . ?
C46 C45 H45 119.9 . . ?
C10 C9 H9 119.8 . . ?
C10 C9 C8 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
N3 C4 C23 110.27(18) . . ?
N3 C4 C5 99.28(17) . . ?
N3 C4 C31 111.02(18) . . ?
C23 C4 C5 110.01(18) . . ?
C31 C4 C23 113.23(19) . . ?
C31 C4 C5 112.18(18) . . ?
C31 C30 H30 118.5 . . ?
C29 C30 C31 122.9(2) . . ?
C29 C30 H30 118.5 . . ?
C37 C38 H38 120.0 . . ?
C39 C38 C37 120.0(2) . . ?
C39 C38 H38 120.0 . . ?
C48 C43 C36 119.3(2) . . ?
C48 C43 C44 118.6(2) . . ?
C44 C43 C36 122.1(2) . . ?
C38 C39 H39 119.8 . . ?
C40 C39 C38 120.4(2) . . ?
C40 C39 H39 119.8 . . ?
C52 C51 C50 120.5(2) . . ?
C52 C51 H51 119.8 . . ?
C50 C51 H51 119.8 . . ?
N3 C15 C14 108.1(2) . . ?
N16 C15 N3 112.7(2) . . ?
N16 C15 C14 138.7(2) . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C54 C49 C2 122.4(2) . . ?
C54 C49 C50 118.7(2) . . ?
C50 C49 C2 118.9(2) . . ?
C41 C40 H40 119.9 . . ?
C39 C40 C41 120.1(2) . . ?
C39 C40 H40 119.9 . . ?

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
C36 N35 C34 N33 2.7(3) . . . . ?
C36 N35 C34 C31 -168.8(2) . . . . ?
N3 C2 C1 N16 3.1(2) . . . . ?
N3 C2 C1 C17 -176.9(2) . . . . ?
N3 C2 C49 C54 58.6(3) . . . . ?
N3 C2 C49 C50 -120.1(2) . . . . ?
N35 C36 C32 C37 174.5(2) . . . . ?
N35 C36 C32 N33 -1.0(3) . . . . ?
N35 C36 C43 C48 -16.3(3) . . . . ?
N35 C36 C43 C44 163.3(2) . . . . ?
N35 C34 C31 C4 -3.6(4) . . . . ?
N35 C34 C31 C30 171.3(2) . . . . ?
C37 C42 C41 C40 -1.4(4) . . . . ?
C37 C38 C39 C40 -1.3(4) . . . . ?
N33 C34 C31 C4 -174.7(2) . . . . ?
N33 C34 C31 C30 0.3(3) . . . . ?
C6 C5 C14 C13 3.8(3) . . . . ?
C6 C5 C14 C15 -178.2(2) . . . . ?
C6 C5 C4 N3 177.7(2) . . . . ?
C6 C5 C4 C23 62.0(3) . . . . ?
C6 C5 C4 C31 -65.0(3) . . . . ?
C6 C11 C12 C13 3.3(4) . . . . ?
C6 C11 C10 C9 -2.2(4) . . . . ?
C6 C7 C8 C9 -1.8(4) . . . . ?
C42 C37 C32 C36 -49.7(4) . . . . ?
C42 C37 C32 N33 125.5(3) . . . . ?
C42 C37 C38 C39 0.4(3) . . . . ?
C42 C41 C40 C39 0.5(4) . . . . ?
C21 C20 C19 C18 2.0(4) . . . . ?
C27 C28 C29 C30 179.0(2) . . . . ?
C27 C26 C25 C24 1.9(4) . . . . ?
C23 C28 C29 C30 -2.9(4) . . . . ?
C23 C24 C25 C26 -0.8(4) . . . . ?
C5 C6 C11 C12 -0.4(3) . . . . ?
C5 C6 C11 C10 178.3(2) . . . . ?
C5 C6 C7 C8 -176.2(2) . . . . ?
C5 C14 C15 N3 0.7(2) . . . . ?
C5 C14 C15 N16 -169.4(3) . . . . ?
C13 C14 C15 N3 178.4(2) . . . . ?
C13 C14 C15 N16 8.3(5) . . . . ?
C28 C27 C26 C25 -0.8(4) . . . . ?
C28 C23 C24 C25 -1.5(3) . . . . ?
C28 C23 C4 N3 125.8(2) . . . . ?
C28 C23 C4 C5 -125.7(2) . . . . ?
C28 C23 C4 C31 0.7(3) . . . . ?
C28 C29 C30 C31 -2.8(4) . . . . ?
C17 C18 C19 C20 -0.6(4) . . . . ?
C14 C5 C4 N3 0.0(2) . . . . ?
C14 C5 C4 C23 -115.7(2) . . . . ?
C14 C5 C4 C31 117.4(2) . . . . ?
C14 C13 C12 C11 -2.6(4) . . . . ?
C11 C6 C5 C14 -3.0(3) . . . . ?
C11 C6 C5 C4 179.5(2) . . . . ?
C11 C6 C7 C8 1.9(4) . . . . ?
C11 C10 C9 C8 2.3(5) . . . . ?
C20 C21 C22 C17 0.1(4) . . . . ?
C18 C17 C22 C21 1.3(3) . . . . ?
C18 C17 C1 N16 28.6(3) . . . . ?
C18 C17 C1 C2 -151.5(2) . . . . ?
C22 C21 C20 C19 -1.7(4) . . . . ?
C22 C17 C18 C19 -1.1(3) . . . . ?
C22 C17 C1 N16 -151.6(2) . . . . ?
C22 C17 C1 C2 28.4(4) . . . . ?
C2 N3 C4 C23 -81.2(3) . . . . ?
C2 N3 C4 C5 163.3(2) . . . . ?
C2 N3 C4 C31 45.1(3) . . . . ?
C2 N3 C15 N16 4.4(3) . . . . ?
C2 N3 C15 C14 -168.55(18) . . . . ?
C32 C36 N35 C34 -1.1(2) . . . . ?
C32 C36 C43 C48 164.4(2) . . . . ?
C32 C36 C43 C44 -16.0(4) . . . . ?
C32 C37 C42 C41 -172.4(2) . . . . ?
C32 C37 C38 C39 173.9(2) . . . . ?
C32 N33 C34 N35 -3.3(3) . . . . ?
C32 N33 C34 C31 168.9(2) . . . . ?
C34 N33 C32 C36 2.5(3) . . . . ?
C34 N33 C32 C37 -173.7(2) . . . . ?
C34 C31 C4 N3 44.2(3) . . . . ?
C34 C31 C4 C23 168.8(2) . . . . ?
C34 C31 C4 C5 -65.9(3) . . . . ?
C34 C31 C30 C29 -167.5(2) . . . . ?
C53 C52 C51 C50 -1.1(5) . . . . ?
C53 C54 C49 C2 179.5(3) . . . . ?
C53 C54 C49 C50 -1.8(4) . . . . ?
C52 C53 C54 C49 0.1(5) . . . . ?
C54 C53 C52 C51 1.4(5) . . . . ?
C1 N16 C15 N3 -2.3(2) . . . . ?
C1 N16 C15 C14 167.4(3) . . . . ?
C1 C17 C18 C19 178.8(2) . . . . ?
C1 C17 C22 C21 -178.5(2) . . . . ?
C1 C2 C49 C54 -131.3(3) . . . . ?
C1 C2 C49 C50 50.0(4) . . . . ?
C7 C6 C5 C14 175.0(2) . . . . ?
C7 C6 C5 C4 -2.4(4) . . . . ?
C7 C6 C11 C12 -178.6(2) . . . . ?
C7 C6 C11 C10 0.1(3) . . . . ?
C26 C27 C28 C23 -1.5(4) . . . . ?
C26 C27 C28 C29 176.6(2) . . . . ?
C12 C13 C14 C5 -0.9(3) . . . . ?
C12 C13 C14 C15 -178.3(2) . . . . ?
C12 C11 C10 C9 176.5(3) . . . . ?
C24 C23 C28 C27 2.6(3) . . . . ?
C24 C23 C28 C29 -175.5(2) . . . . ?
C24 C23 C4 N3 -55.0(3) . . . . ?
C24 C23 C4 C5 53.5(3) . . . . ?
C24 C23 C4 C31 179.9(2) . . . . ?
C10 C11 C12 C13 -175.4(2) . . . . ?
C10 C9 C8 C7 -0.2(5) . . . . ?
C47 C48 C43 C36 179.7(2) . . . . ?
C47 C48 C43 C44 0.1(4) . . . . ?
C47 C46 C45 C44 0.9(4) . . . . ?
C45 C44 C43 C36 179.6(2) . . . . ?
C45 C44 C43 C48 -0.9(3) . . . . ?
C45 C46 C47 C48 -1.7(4) . . . . ?
C4 N3 C2 C1 -167.9(2) . . . . ?
C4 N3 C2 C49 4.6(4) . . . . ?
C4 N3 C15 N16 172.21(18) . . . . ?
C4 N3 C15 C14 -0.7(2) . . . . ?
C4 C23 C28 C27 -178.2(2) . . . . ?
C4 C23 C28 C29 3.7(3) . . . . ?
C4 C23 C24 C25 179.3(2) . . . . ?
C4 C5 C14 C13 -178.4(2) . . . . ?
C4 C5 C14 C15 -0.4(2) . . . . ?
C4 C31 C30 C29 7.4(4) . . . . ?
C30 C31 C4 N3 -130.7(2) . . . . ?
C30 C31 C4 C23 -6.0(3) . . . . ?
C30 C31 C4 C5 119.2(2) . . . . ?
C38 C37 C42 C41 0.9(4) . . . . ?
C38 C37 C32 C36 137.0(3) . . . . ?
C38 C37 C32 N33 -47.8(3) . . . . ?
C38 C39 C40 C41 0.8(4) . . . . ?
C43 C36 N35 C34 179.5(2) . . . . ?
C43 C36 C32 C37 -6.1(4) . . . . ?
C43 C36 C32 N33 178.4(2) . . . . ?
C43 C48 C47 C46 1.2(4) . . . . ?
C43 C44 C45 C46 0.4(4) . . . . ?
C51 C50 C49 C2 -179.2(2) . . . . ?
C51 C50 C49 C54 2.0(4) . . . . ?
C15 N3 C2 C1 -4.3(2) . . . . ?
C15 N3 C2 C49 168.1(2) . . . . ?
C15 N3 C4 C23 115.9(2) . . . . ?
C15 N3 C4 C5 0.4(2) . . . . ?
C15 N3 C4 C31 -117.8(2) . . . . ?
C15 N16 C1 C17 179.4(2) . . . . ?
C15 N16 C1 C2 -0.5(2) . . . . ?
C49 C2 C1 N16 -168.4(2) . . . . ?
C49 C2 C1 C17 11.6(4) . . . . ?
C49 C50 C51 C52 -0.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.283
_oxdiff_exptl_absorpt_empirical_full_min 0.715
####################################################################### 
# 
# 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_220808_byproduct_mutoh
_database_code_depnum_ccdc_archive 'CCDC 2214826'
loop_
_audit_author_name
_audit_author_address
'Katsuya Mutoh'
;Aoyama Gakuin University
Japan
;
_audit_update_record             
;
2022-10-24 deposited with the CCDC.	2023-02-08 downloaded from the CCDC.
;
_audit_creation_date             2022-08-12
_audit_creation_method           
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C52 H36 N4, 2(C6 H6)'
_chemical_formula_sum            'C64 H48 N4'
_chemical_formula_weight         873.06
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   13.5892(3)
_cell_length_b                   17.5461(4)
_cell_length_c                   19.4886(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4646.81(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11003
_cell_measurement_temperature    105(8)
_cell_measurement_theta_max      30.3550
_cell_measurement_theta_min      2.1680
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            35777
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.668
_diffrn_reflns_theta_min         2.165
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      105(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     85.00 110.00   0.50  150.98    --   20.00  54.00-150.00   50
  2  ω      3.00  50.00   0.50  150.98    --   20.00  54.00 -90.00   94
  3  ω    -63.00 -36.00   0.50  150.98    --   20.00  54.00  90.00   54
  4  ω     21.00 110.00   0.50  150.98    --   20.00  54.00  90.00  178
  5  ω    -73.00  35.00   0.50  150.98    --   20.00  54.00-120.00  216
  6  ω     74.00  99.00   0.50  150.98    --   20.00  54.00-120.00   50
  7  ω    -62.00  44.00   0.50  150.98    --   20.00  54.00-150.00  212
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0187793000
_diffrn_orient_matrix_UB_12      -0.0315626000
_diffrn_orient_matrix_UB_13      0.0185506000
_diffrn_orient_matrix_UB_21      0.0035039000
_diffrn_orient_matrix_UB_22      -0.0229394000
_diffrn_orient_matrix_UB_23      -0.0298892000
_diffrn_orient_matrix_UB_31      0.0485773000
_diffrn_orient_matrix_UB_32      -0.0105199000
_diffrn_orient_matrix_UB_33      0.0093755000
_diffrn_oxdiff_digest_frames     
;
011a871325e09e55cfc2028939193e4aac0085467c5
;
_diffrn_oxdiff_digest_hkl        
;
01782d57af580f42bc3964852cddb621ff2ebd
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                9597
_reflns_number_total             13363
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 3175 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     615
_refine_ls_number_reflns         13363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0552
_refine_ls_restrained_S_all      1.012
_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)+(0.0536P)²+0.3238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1144
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C39(H39), C41(H41), C2(H2), C26(H26), C3(H3), C52(H52), C44(H44), C54(H54),
 C33(H33), C42(H42), C25(H25), C37(H37), C43(H43), C29(H29), C24(H24), C35(H35),
  C38(H38), C31(H31), C56(H56), C36(H36), C60(H60), C32(H32), C55(H55),
 C45(H45), C30(H30), C53(H53), C61(H61), C58(H58), C62(H62), C14(H14), C13(H13),
  C48(H48), C59(H59), C46(H46), C57(H57), C66(H66), C65(H65), C64(H64),
 C47(H47), C63(H63), C67(H67), C68(H68)
2.b Idealised Me refined as rotating group:
 C50(H50A,H50B,H50C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N6 N -0.53194(14) -0.67012(11) -0.88777(11) 0.0160(4) Uani 1 1 d . . . . .
N20 N -0.75142(14) -0.68529(11) -0.75855(10) 0.0148(4) Uani 1 1 d . . . . .
N9 N -0.55381(14) -0.75148(11) -0.80164(10) 0.0146(4) Uani 1 1 d . . . . .
N17 N -0.71723(15) -0.68151(12) -0.64639(11) 0.0169(4) Uani 1 1 d . . . . .
C1 C -0.89712(18) -0.73107(14) -0.91572(13) 0.0170(5) Uani 1 1 d . . . . .
C16 C -0.70706(17) -0.72124(14) -0.70382(13) 0.0158(5) Uani 1 1 d . . . . .
C34 C -0.79412(18) -0.56029(14) -0.61029(13) 0.0168(5) Uani 1 1 d . . . . .
C39 C -0.81739(18) -0.58593(15) -0.54474(14) 0.0212(6) Uani 1 1 d . . . . .
H39 H -0.813993 -0.637748 -0.535008 0.025 Uiso 1 1 calc R . . . .
C18 C -0.76885(17) -0.61636(14) -0.66422(13) 0.0159(5) Uani 1 1 d . . . . .
C41 C -0.34496(19) -0.60947(14) -0.94150(13) 0.0193(5) Uani 1 1 d . . . . .
H41 H -0.394279 -0.618844 -0.973490 0.023 Uiso 1 1 calc R . . . .
C2 C -0.81972(18) -0.73164(14) -0.96384(13) 0.0196(5) Uani 1 1 d . . . . .
H2 H -0.834276 -0.732688 -1.010458 0.024 Uiso 1 1 calc R . . . .
C51 C -0.84516(17) -0.56286(13) -0.77722(13) 0.0159(5) Uani 1 1 d . . . . .
C26 C -0.99624(19) -0.73378(15) -0.93825(14) 0.0219(6) Uani 1 1 d . . . . .
H26 H -1.010211 -0.735340 -0.984945 0.026 Uiso 1 1 calc R . . . .
C21 C -0.77463(17) -0.71590(13) -0.82523(13) 0.0150(5) Uani 1 1 d . . . . .
C3 C -0.72430(18) -0.73067(14) -0.94330(13) 0.0186(5) Uani 1 1 d . . . . .
H3 H -0.674427 -0.736293 -0.975580 0.022 Uiso 1 1 calc R . . . .
C40 C -0.35486(18) -0.63644(14) -0.87401(13) 0.0161(5) Uani 1 1 d . . . . .
C22 C -0.87551(17) -0.72817(13) -0.84367(13) 0.0157(5) Uani 1 1 d . . . . .
C8 C -0.45486(17) -0.73050(13) -0.80023(12) 0.0143(5) Uani 1 1 d . . . . .
C23 C -0.95509(18) -0.73676(14) -0.79632(13) 0.0180(5) Uani 1 1 d . . . . .
C52 C -0.93204(18) -0.52950(14) -0.75315(14) 0.0193(5) Uani 1 1 d . . . . .
H52 H -0.955955 -0.542610 -0.710024 0.023 Uiso 1 1 calc R . . . .
C44 C -0.19914(19) -0.57786(15) -0.84633(15) 0.0247(6) Uani 1 1 d . . . . .
H44 H -0.150790 -0.566533 -0.814135 0.030 Uiso 1 1 calc R . . . .
C19 C -0.79083(17) -0.61668(13) -0.73336(13) 0.0158(5) Uani 1 1 d . . . . .
C28 C -0.38739(17) -0.76115(13) -0.74765(12) 0.0156(5) Uani 1 1 d . . . . .
C54 C -0.9499(2) -0.45937(15) -0.85835(14) 0.0239(6) Uani 1 1 d . . . . .
H54 H -0.984722 -0.424933 -0.885309 0.029 Uiso 1 1 calc R . . . .
C33 C -0.30525(18) -0.80407(14) -0.76577(14) 0.0192(5) Uani 1 1 d . . . . .
H33 H -0.291604 -0.813012 -0.811837 0.023 Uiso 1 1 calc R . . . .
C42 C -0.26182(19) -0.56892(15) -0.96051(14) 0.0231(6) Uani 1 1 d . . . . .
H42 H -0.255152 -0.551979 -1.005493 0.028 Uiso 1 1 calc R . . . .
C7 C -0.44322(18) -0.67980(14) -0.85355(13) 0.0158(5) Uani 1 1 d . . . . .
C25 C -1.07095(19) -0.73411(15) -0.89188(14) 0.0237(6) Uani 1 1 d . . . . .
H25 H -1.135898 -0.731733 -0.906757 0.028 Uiso 1 1 calc R . . . .
C37 C -0.8494(2) -0.45757(16) -0.50687(15) 0.0258(6) Uani 1 1 d . . . . .
H37 H -0.868950 -0.423537 -0.472911 0.031 Uiso 1 1 calc R . . . .
C43 C -0.1887(2) -0.55341(15) -0.91321(15) 0.0247(6) Uani 1 1 d . . . . .
H43 H -0.132750 -0.526627 -0.926413 0.030 Uiso 1 1 calc R . . . .
C29 C -0.40686(19) -0.74846(15) -0.67815(14) 0.0218(6) Uani 1 1 d . . . . .
H29 H -0.461619 -0.720043 -0.665310 0.026 Uiso 1 1 calc R . . . .
C4 C -0.70014(17) -0.72123(13) -0.87354(13) 0.0152(5) Uani 1 1 d . . . . .
C24 C -1.04987(19) -0.73803(15) -0.82165(14) 0.0218(6) Uani 1 1 d . . . . .
H24 H -1.101887 -0.741629 -0.790817 0.026 Uiso 1 1 calc R . . . .
C35 C -0.79601(19) -0.48168(14) -0.62289(14) 0.0214(6) Uani 1 1 d . . . . .
H35 H -0.778606 -0.463102 -0.665902 0.026 Uiso 1 1 calc R . . . .
C38 C -0.8457(2) -0.53518(16) -0.49343(14) 0.0245(6) Uani 1 1 d . . . . .
H38 H -0.862165 -0.553346 -0.450089 0.029 Uiso 1 1 calc R . . . .
C31 C -0.2635(2) -0.82057(15) -0.64671(15) 0.0249(6) Uani 1 1 d . . . . .
H31 H -0.222210 -0.840342 -0.613066 0.030 Uiso 1 1 calc R . . . .
C56 C -0.81219(19) -0.54319(14) -0.84279(13) 0.0191(5) Uani 1 1 d . . . . .
H56 H -0.753960 -0.564044 -0.859411 0.023 Uiso 1 1 calc R . . . .
C36 C -0.8238(2) -0.43145(16) -0.57142(14) 0.0256(6) Uani 1 1 d . . . . .
H36 H -0.825114 -0.379419 -0.580450 0.031 Uiso 1 1 calc R . . . .
C15 C -0.65721(17) -0.79503(14) -0.70809(13) 0.0165(5) Uani 1 1 d . . . . .
C60 C -0.3975(2) -0.70206(17) -0.45231(15) 0.0290(7) Uani 1 1 d . . . . .
H60 H -0.351489 -0.724436 -0.423304 0.035 Uiso 1 1 calc R . . . .
C32 C -0.24362(19) -0.83360(15) -0.71567(15) 0.0238(6) Uani 1 1 d . . . . .
H32 H -0.188884 -0.862177 -0.728252 0.029 Uiso 1 1 calc R . . . .
C55 C -0.8653(2) -0.49296(15) -0.88338(14) 0.0216(6) Uani 1 1 d . . . . .
H55 H -0.843848 -0.481853 -0.927577 0.026 Uiso 1 1 calc R . . . .
C12 C -0.55445(19) -0.93442(14) -0.70627(14) 0.0213(6) Uani 1 1 d . . . . .
C5 C -0.59636(18) -0.71303(14) -0.85503(13) 0.0153(5) Uani 1 1 d . . . . .
C45 C -0.28127(19) -0.61918(14) -0.82698(14) 0.0207(6) Uani 1 1 d . . . . .
H45 H -0.287349 -0.635656 -0.781819 0.025 Uiso 1 1 calc R . . . .
C30 C -0.3451(2) -0.77796(16) -0.62842(14) 0.0265(6) Uani 1 1 d . . . . .
H30 H -0.358507 -0.769106 -0.582308 0.032 Uiso 1 1 calc R . . . .
C53 C -0.98288(19) -0.47714(15) -0.79286(14) 0.0217(6) Uani 1 1 d . . . . .
H53 H -1.039172 -0.453876 -0.775608 0.026 Uiso 1 1 calc R . . . .
C11 C -0.54658(17) -0.88646(14) -0.76529(13) 0.0177(5) Uani 1 1 d . . . . .
C49 C -0.49641(18) -0.91466(15) -0.82474(14) 0.0207(6) Uani 1 1 d . . . . .
C61 C -0.3747(2) -0.63576(16) -0.48706(15) 0.0272(6) Uani 1 1 d . . . . .
H61 H -0.312841 -0.613735 -0.481960 0.033 Uiso 1 1 calc R . . . .
C58 C -0.5578(2) -0.70281(18) -0.50340(15) 0.0311(7) Uani 1 1 d . . . . .
H58 H -0.619075 -0.725566 -0.509305 0.037 Uiso 1 1 calc R . . . .
C50 C -0.5008(2) -0.87611(16) -0.89391(14) 0.0242(6) Uani 1 1 d . . . . .
H50A H -0.462031 -0.830366 -0.892813 0.036 Uiso 1 1 calc GR . . . .
H50B H -0.567802 -0.863555 -0.904574 0.036 Uiso 1 1 calc GR . . . .
H50C H -0.475226 -0.909876 -0.928333 0.036 Uiso 1 1 calc GR . . . .
C62 C -0.4442(2) -0.60199(17) -0.52972(15) 0.0303(7) Uani 1 1 d . . . . .
H62 H -0.429568 -0.556950 -0.552706 0.036 Uiso 1 1 calc R . . . .
C14 C -0.67099(19) -0.84792(15) -0.65369(14) 0.0221(6) Uani 1 1 d . . . . .
H14 H -0.716939 -0.837837 -0.619505 0.027 Uiso 1 1 calc R . . . .
C13 C -0.6171(2) -0.91330(15) -0.65147(15) 0.0241(6) Uani 1 1 d . . . . .
H13 H -0.621624 -0.944721 -0.613168 0.029 Uiso 1 1 calc R . . . .
C48 C -0.4493(2) -0.98431(15) -0.81981(16) 0.0260(6) Uani 1 1 d . . . . .
H48 H -0.416823 -1.003245 -0.858190 0.031 Uiso 1 1 calc R . . . .
C27 C -0.9411(2) -0.75172(16) -0.72036(14) 0.0250(6) Uani 1 1 d . . . . .
H27A H -0.925147 -0.704854 -0.697496 0.037 Uiso 1 1 calc GR . . . .
H27B H -0.888553 -0.787585 -0.713975 0.037 Uiso 1 1 calc GR . . . .
H27C H -1.000764 -0.772185 -0.701474 0.037 Uiso 1 1 calc GR . . . .
C10 C -0.59193(17) -0.81249(14) -0.75969(13) 0.0159(5) Uani 1 1 d . . . . .
C59 C -0.4893(2) -0.73508(18) -0.46087(16) 0.0337(7) Uani 1 1 d . . . . .
H59 H -0.504569 -0.779716 -0.437442 0.040 Uiso 1 1 calc R . . . .
C46 C -0.5014(2) -1.00382(15) -0.70350(16) 0.0265(6) Uani 1 1 d . . . . .
H46 H -0.502626 -1.033190 -0.663783 0.032 Uiso 1 1 calc R . . . .
C57 C -0.5349(2) -0.63571(18) -0.53761(16) 0.0328(7) Uani 1 1 d . . . . .
H57 H -0.581366 -0.613294 -0.566228 0.039 Uiso 1 1 calc R . . . .
C66 C -0.2548(2) -0.50508(19) -0.66746(16) 0.0359(7) Uani 1 1 d . . . . .
H66 H -0.313490 -0.502668 -0.691881 0.043 Uiso 1 1 calc R . . . .
C65 C -0.2274(2) -0.57168(18) -0.63631(17) 0.0374(8) Uani 1 1 d . . . . .
H65 H -0.267031 -0.614690 -0.639972 0.045 Uiso 1 1 calc R . . . .
C64 C -0.1408(3) -0.5749(2) -0.59947(17) 0.0430(9) Uani 1 1 d . . . . .
H64 H -0.122193 -0.619794 -0.577761 0.052 Uiso 1 1 calc R . . . .
C47 C -0.4486(2) -1.02770(15) -0.75909(16) 0.0296(7) Uani 1 1 d . . . . .
H47 H -0.412193 -1.072514 -0.756821 0.035 Uiso 1 1 calc R . . . .
C63 C -0.0816(2) -0.5105(2) -0.59500(18) 0.0436(9) Uani 1 1 d . . . . .
H63 H -0.022930 -0.512257 -0.570526 0.052 Uiso 1 1 calc R . . . .
C67 C -0.1959(3) -0.44200(19) -0.66270(16) 0.0395(8) Uani 1 1 d . . . . .
H67 H -0.214667 -0.397000 -0.684244 0.047 Uiso 1 1 calc R . . . .
C68 C -0.1101(3) -0.4445(2) -0.62676(18) 0.0404(8) Uani 1 1 d . . . . .
H68 H -0.070660 -0.401301 -0.623780 0.049 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
N6 C7 1.388(3) . ?
N6 C5 1.319(3) . ?
N20 C16 1.378(3) . ?
N20 C21 1.441(3) . ?
N20 C19 1.406(3) . ?
N9 C8 1.394(3) . ?
N9 C5 1.368(3) . ?
N9 C10 1.443(3) . ?
N17 C16 1.326(3) . ?
N17 C18 1.386(3) . ?
C1 C2 1.409(4) . ?
C1 C26 1.418(3) . ?
C1 C22 1.435(3) . ?
C16 C15 1.464(3) . ?
C34 C39 1.391(4) . ?
C34 C18 1.480(3) . ?
C34 C35 1.401(3) . ?
C39 H39 0.9300 . ?
C39 C38 1.393(4) . ?
C18 C19 1.380(3) . ?
C41 H41 0.9300 . ?
C41 C40 1.404(4) . ?
C41 C42 1.386(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.357(4) . ?
C51 C52 1.399(3) . ?
C51 C19 1.472(3) . ?
C51 C56 1.397(3) . ?
C26 H26 0.9300 . ?
C26 C25 1.359(4) . ?
C21 C22 1.433(3) . ?
C21 C4 1.386(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.408(3) . ?
C40 C7 1.476(3) . ?
C40 C45 1.390(4) . ?
C22 C23 1.430(3) . ?
C8 C28 1.476(3) . ?
C8 C7 1.377(3) . ?
C23 C24 1.380(4) . ?
C23 C27 1.515(4) . ?
C52 H52 0.9300 . ?
C52 C53 1.386(4) . ?
C44 H44 0.9300 . ?
C44 C43 1.380(4) . ?
C44 C45 1.383(4) . ?
C28 C33 1.392(3) . ?
C28 C29 1.398(3) . ?
C54 H54 0.9300 . ?
C54 C55 1.381(4) . ?
C54 C53 1.388(4) . ?
C33 H33 0.9300 . ?
C33 C32 1.387(4) . ?
C42 H42 0.9300 . ?
C42 C43 1.382(4) . ?
C25 H25 0.9300 . ?
C25 C24 1.400(4) . ?
C37 H37 0.9300 . ?
C37 C38 1.388(4) . ?
C37 C36 1.384(4) . ?
C43 H43 0.9300 . ?
C29 H29 0.9300 . ?
C29 C30 1.383(4) . ?
C4 C5 1.463(3) . ?
C24 H24 0.9300 . ?
C35 H35 0.9300 . ?
C35 C36 1.387(4) . ?
C38 H38 0.9300 . ?
C31 H31 0.9300 . ?
C31 C32 1.390(4) . ?
C31 C30 1.384(4) . ?
C56 H56 0.9300 . ?
C56 C55 1.387(4) . ?
C36 H36 0.9300 . ?
C15 C14 1.421(4) . ?
C15 C10 1.375(3) . ?
C60 H60 0.9300 . ?
C60 C61 1.381(4) . ?
C60 C59 1.385(4) . ?
C32 H32 0.9300 . ?
C55 H55 0.9300 . ?
C12 C11 1.429(4) . ?
C12 C13 1.415(4) . ?
C12 C46 1.416(4) . ?
C45 H45 0.9300 . ?
C30 H30 0.9300 . ?
C53 H53 0.9300 . ?
C11 C49 1.432(4) . ?
C11 C10 1.441(3) . ?
C49 C50 1.509(4) . ?
C49 C48 1.383(4) . ?
C61 H61 0.9300 . ?
C61 C62 1.392(4) . ?
C58 H58 0.9300 . ?
C58 C59 1.369(4) . ?
C58 C57 1.389(4) . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C62 H62 0.9300 . ?
C62 C57 1.375(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.361(4) . ?
C13 H13 0.9300 . ?
C48 H48 0.9300 . ?
C48 C47 1.407(4) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C59 H59 0.9300 . ?
C46 H46 0.9300 . ?
C46 C47 1.366(4) . ?
C57 H57 0.9300 . ?
C66 H66 0.9300 . ?
C66 C65 1.368(5) . ?
C66 C67 1.369(5) . ?
C65 H65 0.9300 . ?
C65 C64 1.379(5) . ?
C64 H64 0.9300 . ?
C64 C63 1.389(5) . ?
C47 H47 0.9300 . ?
C63 H63 0.9300 . ?
C63 C68 1.369(5) . ?
C67 H67 0.9300 . ?
C67 C68 1.361(5) . ?
C68 H68 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
C5 N6 C7 105.9(2) . . ?
C16 N20 C21 128.5(2) . . ?
C16 N20 C19 106.76(19) . . ?
C19 N20 C21 123.41(19) . . ?
C8 N9 C10 122.1(2) . . ?
C5 N9 C8 107.0(2) . . ?
C5 N9 C10 130.2(2) . . ?
C16 N17 C18 106.0(2) . . ?
C2 C1 C26 120.2(2) . . ?
C2 C1 C22 119.9(2) . . ?
C26 C1 C22 119.9(2) . . ?
N20 C16 C15 124.3(2) . . ?
N17 C16 N20 111.5(2) . . ?
N17 C16 C15 124.2(2) . . ?
C39 C34 C18 119.4(2) . . ?
C39 C34 C35 118.4(2) . . ?
C35 C34 C18 122.3(2) . . ?
C34 C39 H39 119.5 . . ?
C34 C39 C38 121.0(2) . . ?
C38 C39 H39 119.5 . . ?
N17 C18 C34 119.2(2) . . ?
C19 C18 N17 110.6(2) . . ?
C19 C18 C34 130.2(2) . . ?
C40 C41 H41 119.9 . . ?
C42 C41 H41 119.9 . . ?
C42 C41 C40 120.1(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.1(2) . . ?
C3 C2 H2 119.4 . . ?
C52 C51 C19 119.8(2) . . ?
C56 C51 C52 118.3(2) . . ?
C56 C51 C19 121.9(2) . . ?
C1 C26 H26 119.9 . . ?
C25 C26 C1 120.3(2) . . ?
C25 C26 H26 119.9 . . ?
C22 C21 N20 119.4(2) . . ?
C4 C21 N20 118.6(2) . . ?
C4 C21 C22 121.2(2) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C41 C40 C7 120.3(2) . . ?
C45 C40 C41 118.4(2) . . ?
C45 C40 C7 121.3(2) . . ?
C21 C22 C1 116.5(2) . . ?
C23 C22 C1 118.2(2) . . ?
C23 C22 C21 125.3(2) . . ?
N9 C8 C28 121.1(2) . . ?
C7 C8 N9 105.5(2) . . ?
C7 C8 C28 133.4(2) . . ?
C22 C23 C27 123.6(2) . . ?
C24 C23 C22 118.5(2) . . ?
C24 C23 C27 117.6(2) . . ?
C51 C52 H52 119.6 . . ?
C53 C52 C51 120.7(2) . . ?
C53 C52 H52 119.6 . . ?
C43 C44 H44 119.9 . . ?
C43 C44 C45 120.2(3) . . ?
C45 C44 H44 119.9 . . ?
N20 C19 C51 122.5(2) . . ?
C18 C19 N20 105.2(2) . . ?
C18 C19 C51 132.3(2) . . ?
C33 C28 C8 121.3(2) . . ?
C33 C28 C29 118.9(2) . . ?
C29 C28 C8 119.8(2) . . ?
C55 C54 H54 120.1 . . ?
C55 C54 C53 119.8(2) . . ?
C53 C54 H54 120.1 . . ?
C28 C33 H33 119.7 . . ?
C32 C33 C28 120.5(2) . . ?
C32 C33 H33 119.7 . . ?
C41 C42 H42 119.7 . . ?
C41 C42 C43 120.6(2) . . ?
C43 C42 H42 119.7 . . ?
N6 C7 C40 120.9(2) . . ?
C8 C7 N6 110.0(2) . . ?
C8 C7 C40 129.1(2) . . ?
C26 C25 H25 120.1 . . ?
C26 C25 C24 119.8(2) . . ?
C24 C25 H25 120.1 . . ?
C38 C37 H37 120.4 . . ?
C36 C37 H37 120.4 . . ?
C36 C37 C38 119.2(3) . . ?
C44 C43 C42 119.7(2) . . ?
C44 C43 H43 120.2 . . ?
C42 C43 H43 120.2 . . ?
C28 C29 H29 119.8 . . ?
C30 C29 C28 120.3(2) . . ?
C30 C29 H29 119.8 . . ?
C21 C4 C3 119.6(2) . . ?
C21 C4 C5 122.0(2) . . ?
C3 C4 C5 118.3(2) . . ?
C23 C24 C25 122.7(2) . . ?
C23 C24 H24 118.7 . . ?
C25 C24 H24 118.7 . . ?
C34 C35 H35 119.9 . . ?
C36 C35 C34 120.2(3) . . ?
C36 C35 H35 119.9 . . ?
C39 C38 H38 119.9 . . ?
C37 C38 C39 120.1(3) . . ?
C37 C38 H38 119.9 . . ?
C32 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
C30 C31 C32 119.6(2) . . ?
C51 C56 H56 119.6 . . ?
C55 C56 C51 120.8(2) . . ?
C55 C56 H56 119.6 . . ?
C37 C36 C35 121.0(3) . . ?
C37 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C14 C15 C16 118.3(2) . . ?
C10 C15 C16 122.5(2) . . ?
C10 C15 C14 119.0(2) . . ?
C61 C60 H60 120.1 . . ?
C61 C60 C59 119.7(3) . . ?
C59 C60 H60 120.1 . . ?
C33 C32 C31 120.1(2) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C54 C55 C56 120.2(3) . . ?
C54 C55 H55 119.9 . . ?
C56 C55 H55 119.9 . . ?
C13 C12 C11 119.9(2) . . ?
C46 C12 C11 119.9(2) . . ?
C46 C12 C13 120.2(2) . . ?
N6 C5 N9 111.6(2) . . ?
N6 C5 C4 125.2(2) . . ?
N9 C5 C4 123.1(2) . . ?
C40 C45 H45 119.5 . . ?
C44 C45 C40 121.0(3) . . ?
C44 C45 H45 119.5 . . ?
C29 C30 C31 120.5(3) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C52 C53 C54 120.1(2) . . ?
C52 C53 H53 119.9 . . ?
C54 C53 H53 119.9 . . ?
C12 C11 C49 118.9(2) . . ?
C12 C11 C10 115.9(2) . . ?
C49 C11 C10 125.2(2) . . ?
C11 C49 C50 123.3(2) . . ?
C48 C49 C11 118.0(3) . . ?
C48 C49 C50 118.4(2) . . ?
C60 C61 H61 120.0 . . ?
C60 C61 C62 119.9(3) . . ?
C62 C61 H61 120.0 . . ?
C59 C58 H58 120.4 . . ?
C59 C58 C57 119.2(3) . . ?
C57 C58 H58 120.4 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C61 C62 H62 120.3 . . ?
C57 C62 C61 119.5(3) . . ?
C57 C62 H62 120.3 . . ?
C15 C14 H14 119.9 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H13 119.3 . . ?
C49 C48 H48 118.7 . . ?
C49 C48 C47 122.7(3) . . ?
C47 C48 H48 118.7 . . ?
C23 C27 H27A 109.5 . . ?
C23 C27 H27B 109.5 . . ?
C23 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C15 C10 N9 118.7(2) . . ?
C15 C10 C11 122.1(2) . . ?
C11 C10 N9 118.1(2) . . ?
C60 C59 H59 119.6 . . ?
C58 C59 C60 120.8(3) . . ?
C58 C59 H59 119.6 . . ?
C12 C46 H46 120.0 . . ?
C47 C46 C12 120.1(3) . . ?
C47 C46 H46 120.0 . . ?
C58 C57 H57 119.6 . . ?
C62 C57 C58 120.8(3) . . ?
C62 C57 H57 119.6 . . ?
C65 C66 H66 120.0 . . ?
C67 C66 H66 120.0 . . ?
C67 C66 C65 120.1(3) . . ?
C66 C65 H65 120.1 . . ?
C66 C65 C64 119.8(3) . . ?
C64 C65 H65 120.1 . . ?
C65 C64 H64 120.2 . . ?
C65 C64 C63 119.6(3) . . ?
C63 C64 H64 120.2 . . ?
C48 C47 H47 120.1 . . ?
C46 C47 C48 119.8(3) . . ?
C46 C47 H47 120.1 . . ?
C64 C63 H63 120.1 . . ?
C68 C63 C64 119.7(3) . . ?
C68 C63 H63 120.1 . . ?
C66 C67 H67 119.7 . . ?
C68 C67 C66 120.6(3) . . ?
C68 C67 H67 119.7 . . ?
C63 C68 H68 119.9 . . ?
C67 C68 C63 120.1(3) . . ?
C67 C68 H68 119.9 . . ?

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
N20 C16 C15 C14 -139.3(2) . . . . ?
N20 C16 C15 C10 46.0(4) . . . . ?
N20 C21 C22 C1 157.6(2) . . . . ?
N20 C21 C22 C23 -21.6(4) . . . . ?
N20 C21 C4 C3 -162.7(2) . . . . ?
N20 C21 C4 C5 13.7(3) . . . . ?
N9 C8 C28 C33 119.2(3) . . . . ?
N9 C8 C28 C29 -59.4(3) . . . . ?
N9 C8 C7 N6 -0.7(3) . . . . ?
N9 C8 C7 C40 176.6(2) . . . . ?
N17 C16 C15 C14 39.0(4) . . . . ?
N17 C16 C15 C10 -135.7(3) . . . . ?
N17 C18 C19 N20 0.4(3) . . . . ?
N17 C18 C19 C51 178.6(2) . . . . ?
C1 C2 C3 C4 -6.5(4) . . . . ?
C1 C26 C25 C24 -5.2(4) . . . . ?
C1 C22 C23 C24 -7.8(4) . . . . ?
C1 C22 C23 C27 166.4(2) . . . . ?
C16 N20 C21 C22 110.4(3) . . . . ?
C16 N20 C21 C4 -79.7(3) . . . . ?
C16 N20 C19 C18 -1.0(2) . . . . ?
C16 N20 C19 C51 -179.4(2) . . . . ?
C16 N17 C18 C34 178.7(2) . . . . ?
C16 N17 C18 C19 0.3(3) . . . . ?
C16 C15 C14 C13 -172.2(2) . . . . ?
C16 C15 C10 N9 14.6(4) . . . . ?
C16 C15 C10 C11 -177.1(2) . . . . ?
C34 C39 C38 C37 -1.1(4) . . . . ?
C34 C18 C19 N20 -177.8(2) . . . . ?
C34 C18 C19 C51 0.4(4) . . . . ?
C34 C35 C36 C37 0.4(4) . . . . ?
C39 C34 C18 N17 -35.3(3) . . . . ?
C39 C34 C18 C19 142.7(3) . . . . ?
C39 C34 C35 C36 -2.1(4) . . . . ?
C18 N17 C16 N20 -1.0(3) . . . . ?
C18 N17 C16 C15 -179.5(2) . . . . ?
C18 C34 C39 C38 -177.2(2) . . . . ?
C18 C34 C35 C36 177.5(2) . . . . ?
C41 C40 C7 N6 -25.8(4) . . . . ?
C41 C40 C7 C8 157.1(3) . . . . ?
C41 C40 C45 C44 -1.4(4) . . . . ?
C41 C42 C43 C44 -0.7(4) . . . . ?
C2 C1 C26 C25 179.3(3) . . . . ?
C2 C1 C22 C21 7.9(4) . . . . ?
C2 C1 C22 C23 -172.7(2) . . . . ?
C2 C3 C4 C21 2.6(4) . . . . ?
C2 C3 C4 C5 -174.0(2) . . . . ?
C51 C52 C53 C54 2.5(4) . . . . ?
C51 C56 C55 C54 2.4(4) . . . . ?
C26 C1 C2 C3 -178.6(3) . . . . ?
C26 C1 C22 C21 -172.4(2) . . . . ?
C26 C1 C22 C23 6.9(4) . . . . ?
C26 C25 C24 C23 4.2(4) . . . . ?
C21 N20 C16 N17 -165.9(2) . . . . ?
C21 N20 C16 C15 12.5(4) . . . . ?
C21 N20 C19 C18 167.0(2) . . . . ?
C21 N20 C19 C51 -11.4(3) . . . . ?
C21 C22 C23 C24 171.4(2) . . . . ?
C21 C22 C23 C27 -14.3(4) . . . . ?
C21 C4 C5 N6 -132.6(3) . . . . ?
C21 C4 C5 N9 49.2(3) . . . . ?
C3 C4 C5 N6 43.9(4) . . . . ?
C3 C4 C5 N9 -134.3(2) . . . . ?
C40 C41 C42 C43 -1.1(4) . . . . ?
C22 C1 C2 C3 1.0(4) . . . . ?
C22 C1 C26 C25 -0.4(4) . . . . ?
C22 C21 C4 C3 7.0(4) . . . . ?
C22 C21 C4 C5 -176.6(2) . . . . ?
C22 C23 C24 C25 2.4(4) . . . . ?
C8 N9 C5 N6 0.6(3) . . . . ?
C8 N9 C5 C4 179.1(2) . . . . ?
C8 N9 C10 C15 113.3(3) . . . . ?
C8 N9 C10 C11 -55.5(3) . . . . ?
C8 C28 C33 C32 -178.8(2) . . . . ?
C8 C28 C29 C30 178.9(2) . . . . ?
C52 C51 C19 N20 136.4(2) . . . . ?
C52 C51 C19 C18 -41.5(4) . . . . ?
C52 C51 C56 C55 -1.2(4) . . . . ?
C19 N20 C16 N17 1.3(3) . . . . ?
C19 N20 C16 C15 179.7(2) . . . . ?
C19 N20 C21 C22 -54.8(3) . . . . ?
C19 N20 C21 C4 115.0(3) . . . . ?
C19 C51 C52 C53 178.2(2) . . . . ?
C19 C51 C56 C55 179.3(2) . . . . ?
C28 C8 C7 N6 -179.6(2) . . . . ?
C28 C8 C7 C40 -2.2(5) . . . . ?
C28 C33 C32 C31 0.0(4) . . . . ?
C28 C29 C30 C31 -0.2(4) . . . . ?
C33 C28 C29 C30 0.2(4) . . . . ?
C42 C41 C40 C7 -179.9(2) . . . . ?
C42 C41 C40 C45 2.1(4) . . . . ?
C7 N6 C5 N9 -1.1(3) . . . . ?
C7 N6 C5 C4 -179.4(2) . . . . ?
C7 C40 C45 C44 -179.3(2) . . . . ?
C7 C8 C28 C33 -62.1(4) . . . . ?
C7 C8 C28 C29 119.3(3) . . . . ?
C43 C44 C45 C40 -0.4(4) . . . . ?
C29 C28 C33 C32 -0.2(4) . . . . ?
C4 C21 C22 C1 -11.9(3) . . . . ?
C4 C21 C22 C23 168.8(2) . . . . ?
C35 C34 C39 C38 2.5(4) . . . . ?
C35 C34 C18 N17 145.0(2) . . . . ?
C35 C34 C18 C19 -36.9(4) . . . . ?
C38 C37 C36 C35 1.0(4) . . . . ?
C56 C51 C52 C53 -1.3(4) . . . . ?
C56 C51 C19 N20 -44.1(3) . . . . ?
C56 C51 C19 C18 138.0(3) . . . . ?
C36 C37 C38 C39 -0.7(4) . . . . ?
C15 C14 C13 C12 -6.9(4) . . . . ?
C60 C61 C62 C57 -0.9(4) . . . . ?
C32 C31 C30 C29 0.1(4) . . . . ?
C55 C54 C53 C52 -1.2(4) . . . . ?
C12 C11 C49 C50 167.5(2) . . . . ?
C12 C11 C49 C48 -6.3(4) . . . . ?
C12 C11 C10 N9 154.1(2) . . . . ?
C12 C11 C10 C15 -14.3(4) . . . . ?
C12 C46 C47 C48 -1.9(4) . . . . ?
C5 N6 C7 C40 -176.5(2) . . . . ?
C5 N6 C7 C8 1.1(3) . . . . ?
C5 N9 C8 C28 179.1(2) . . . . ?
C5 N9 C8 C7 0.1(3) . . . . ?
C5 N9 C10 C15 -78.3(3) . . . . ?
C5 N9 C10 C11 113.0(3) . . . . ?
C45 C40 C7 N6 152.1(2) . . . . ?
C45 C40 C7 C8 -25.0(4) . . . . ?
C45 C44 C43 C42 1.5(4) . . . . ?
C30 C31 C32 C33 0.0(4) . . . . ?
C53 C54 C55 C56 -1.3(4) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C11 C12 C46 C47 -4.8(4) . . . . ?
C11 C49 C48 C47 -0.3(4) . . . . ?
C49 C11 C10 N9 -26.6(4) . . . . ?
C49 C11 C10 C15 165.1(2) . . . . ?
C49 C48 C47 C46 4.6(4) . . . . ?
C61 C60 C59 C58 0.0(5) . . . . ?
C61 C62 C57 C58 0.2(5) . . . . ?
C50 C49 C48 C47 -174.5(3) . . . . ?
C14 C15 C10 N9 -160.1(2) . . . . ?
C14 C15 C10 C11 8.2(4) . . . . ?
C13 C12 C11 C49 -169.5(2) . . . . ?
C13 C12 C11 C10 9.9(4) . . . . ?
C13 C12 C46 C47 173.6(3) . . . . ?
C27 C23 C24 C25 -172.2(3) . . . . ?
C10 N9 C8 C28 -10.1(3) . . . . ?
C10 N9 C8 C7 170.9(2) . . . . ?
C10 N9 C5 N6 -169.1(2) . . . . ?
C10 N9 C5 C4 9.3(4) . . . . ?
C10 C15 C14 C13 2.7(4) . . . . ?
C10 C11 C49 C50 -11.8(4) . . . . ?
C10 C11 C49 C48 174.4(2) . . . . ?
C59 C60 C61 C62 0.8(4) . . . . ?
C59 C58 C57 C62 0.6(5) . . . . ?
C46 C12 C11 C49 8.9(4) . . . . ?
C46 C12 C11 C10 -171.7(2) . . . . ?
C46 C12 C13 C14 -178.2(3) . . . . ?
C57 C58 C59 C60 -0.7(5) . . . . ?
C66 C65 C64 C63 -0.7(5) . . . . ?
C66 C67 C68 C63 0.1(5) . . . . ?
C65 C66 C67 C68 -0.4(5) . . . . ?
C65 C64 C63 C68 0.4(5) . . . . ?
C64 C63 C68 C67 -0.1(5) . . . . ?
C67 C66 C65 C64 0.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.060
_oxdiff_exptl_absorpt_empirical_full_min 0.951
