# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2021

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

data_Compound_1d
_database_code_depnum_ccdc_archive 'CCDC 2034947'
loop_
_audit_author_name
_audit_author_address
'Masashi Mamada'
;Kyushu University
Japan
;
_audit_update_record             
;
2020-10-01 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;
_audit_creation_date             2020-09-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H16 N2'
_chemical_formula_sum            'C24 H16 N2'
_chemical_formula_weight         332.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     100K
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   3.8901(6)
_cell_length_b                   6.4671(9)
_cell_length_c                   17.778(4)
_cell_angle_alpha                81.896(14)
_cell_angle_beta                 85.023(15)
_cell_angle_gamma                85.150(12)
_cell_volume                     439.93(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    723
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.0360
_cell_measurement_theta_min      4.1700
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             174
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.050
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            2899
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_min         2.321
_diffrn_ambient_temperature      100
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_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  31.00   0.50   27.00    --  -10.30  45.00  30.00  184
  2  ω    -93.00  54.00   0.50   27.00    --  -10.30  45.00 150.00  294
  3  ω    -97.00  78.00   0.50   27.00    --  -10.30  45.00  90.00  350
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC HyPix-6000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0008447000
_diffrn_orient_matrix_UB_12      -0.0159121000
_diffrn_orient_matrix_UB_13      -0.0386498000
_diffrn_orient_matrix_UB_21      0.0138616000
_diffrn_orient_matrix_UB_22      -0.1099376000
_diffrn_orient_matrix_UB_23      0.0110888000
_diffrn_orient_matrix_UB_31      -0.1829930000
_diffrn_orient_matrix_UB_32      -0.0000869000
_diffrn_orient_matrix_UB_33      0.0040933000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR-E+
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2383
_reflns_number_total             2899
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0986
_refine_ls_restrained_S_all      1.160
_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)+(0.1186P)²+0.8597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2696
_refine_ls_wR_factor_ref         0.2775
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.461(4)
 0.539(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9115(11) 0.3530(6) 0.4591(3) 0.0154(9) Uani 1 1 d . . . . .
C2 C 0.8216(11) 0.3310(7) 0.5359(3) 0.0166(9) Uani 1 1 d . . . . .
H2 H 0.704351 0.212558 0.559183 0.020 Uiso 1 1 calc R U . . .
C3 C 0.8993(10) 0.4798(6) 0.5808(3) 0.0150(9) Uani 1 1 d . . . . .
C4 C 0.8141(11) 0.1947(6) 0.4162(3) 0.0158(9) Uani 1 1 d . . . . .
C5 C 0.7945(11) 0.4725(7) 0.6616(2) 0.0158(9) Uani 1 1 d . . . . .
H5 H 0.859474 0.581403 0.686919 0.019 Uiso 1 1 calc R U . . .
C6 C 0.6130(11) 0.3232(7) 0.7028(3) 0.0190(10) Uani 1 1 d . . . . .
H6 H 0.555257 0.212530 0.677416 0.023 Uiso 1 1 calc R U . . .
C7 C 0.4958(11) 0.3155(7) 0.7835(3) 0.0186(9) Uani 1 1 d . . . . .
C8 C 0.5138(12) 0.4834(7) 0.8244(3) 0.0259(11) Uani 1 1 d . . . . .
H8 H 0.608194 0.608283 0.799693 0.031 Uiso 1 1 calc R U . . .
C9 C 0.3947(13) 0.4691(8) 0.9009(3) 0.0277(11) Uani 1 1 d . . . . .
H9 H 0.404978 0.584693 0.928030 0.033 Uiso 1 1 calc R U . . .
C10 C 0.2615(13) 0.2867(9) 0.9374(3) 0.0322(12) Uani 1 1 d . . . . .
H10 H 0.187109 0.275587 0.990073 0.039 Uiso 1 1 calc R U . . .
C11 C 0.2360(14) 0.1206(9) 0.8977(3) 0.0310(12) Uani 1 1 d . . . . .
H11 H 0.139796 -0.003637 0.922516 0.037 Uiso 1 1 calc R U . . .
C12 C 0.3509(12) 0.1362(7) 0.8219(3) 0.0237(11) Uani 1 1 d . . . . .
H12 H 0.331115 0.021691 0.794803 0.028 Uiso 1 1 calc R U . . .
N1 N 0.7260(9) 0.0706(6) 0.3840(2) 0.0200(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.371(7) . ?
C1 C3 1.429(6) 2_766 ?
C1 C4 1.452(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(6) . ?
C3 C5 1.453(6) . ?
C4 N1 1.140(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.340(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.462(6) . ?
C7 C8 1.399(6) . ?
C7 C12 1.395(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.375(7) . ?
C12 H12 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
C2 C1 C3 123.8(4) . 2_766 ?
C2 C1 C4 117.9(4) . . ?
C3 C1 C4 118.2(4) 2_766 . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.3(4) . . ?
C3 C2 H2 119.4 . . ?
C1 C3 C5 121.0(4) 2_766 . ?
C2 C3 C1 114.9(4) . 2_766 ?
C2 C3 C5 124.1(4) . . ?
N1 C4 C1 177.5(5) . . ?
C3 C5 H5 117.6 . . ?
C6 C5 C3 124.7(4) . . ?
C6 C5 H5 117.6 . . ?
C5 C6 H6 117.1 . . ?
C5 C6 C7 125.8(4) . . ?
C7 C6 H6 117.1 . . ?
C8 C7 C6 122.8(4) . . ?
C12 C7 C6 119.4(4) . . ?
C12 C7 C8 117.7(4) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.6(4) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.9(5) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(5) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.5(5) . . ?
C12 C11 H11 120.2 . . ?
C7 C12 H12 119.0 . . ?
C11 C12 C7 121.9(5) . . ?
C11 C12 H12 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C1 -2.5(7) . . . 2_766 ?
C1 C2 C3 C5 176.4(5) . . . . ?
C1 C3 C5 C6 179.0(4) 2_766 . . . ?
C2 C3 C5 C6 0.2(7) . . . . ?
C3 C1 C2 C3 2.7(7) 2_766 . . . ?
C3 C5 C6 C7 -178.1(5) . . . . ?
C4 C1 C2 C3 -178.5(4) . . . . ?
C5 C6 C7 C8 10.6(7) . . . . ?
C5 C6 C7 C12 -171.1(5) . . . . ?
C6 C7 C8 C9 179.2(5) . . . . ?
C6 C7 C12 C11 -179.9(5) . . . . ?
C7 C8 C9 C10 0.9(8) . . . . ?
C8 C7 C12 C11 -1.5(7) . . . . ?
C8 C9 C10 C11 -2.0(8) . . . . ?
C9 C10 C11 C12 1.4(8) . . . . ?
C10 C11 C12 C7 0.4(8) . . . . ?
C12 C7 C8 C9 0.9(7) . . . . ?

_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 1.589
_oxdiff_exptl_absorpt_empirical_full_min 0.693
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.461(4) 1310 4277 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.539(4) 1324 4277 nmt -0.9996 0.0000 0.0000 -0.0007 -0.9999 0.0002 -0.7337
-0.7325 0.9992

_twin_special_details            
;
Component 2 rotated by -179.9870° 
 around [-0.00 0.00 1.00] (reciprocal) or [-0.33 -0.33 0.89] (direct)
;
####################################################################### 
# 
# 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_Compound_2c
_database_code_depnum_ccdc_archive 'CCDC 2034949'
loop_
_audit_author_name
_audit_author_address
'Masashi Mamada'
;Kyushu University
Japan
;
_audit_update_record             
;
2020-10-01 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C36 H24 N2'
_chemical_formula_moiety         'C36 H24 N2'
_chemical_formula_weight         484.60
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   26.5004(14)
_cell_length_b                   6.9730(4)
_cell_length_c                   6.8292(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.180(6)
_cell_angle_gamma                90.0000
_cell_volume                     1261.95(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9003
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    183
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508.00
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_T_max  0.972

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      183
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            14004
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_theta_max         68.235
_diffrn_reflns_theta_min         3.336
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2309
_reflns_number_gt                1631
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1434
_refine_ls_wR_factor_gt          0.1286
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2309
_refine_ls_number_parameters     172
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0469P)²+0.9451P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N20 N 0.12889(8) 0.9945(4) -0.4571(3) 0.0560(7) Uani 1 4 d . . .
C1 C 0.05322(8) 0.9993(4) 0.0149(4) 0.0382(6) Uani 1 4 d . . .
C2 C 0.02872(9) 1.0731(4) -0.1500(4) 0.0457(7) Uani 1 4 d . . .
C3 C 0.02320(9) 0.9283(4) 0.1640(4) 0.0446(7) Uani 1 4 d . . .
C4 C 0.10799(9) 0.9946(4) 0.0462(4) 0.0411(6) Uani 1 4 d . . .
C5 C 0.14536(9) 0.9990(4) -0.0843(4) 0.0374(6) Uani 1 4 d . . .
C6 C 0.13457(8) 0.9973(4) -0.2921(4) 0.0382(6) Uani 1 4 d . . .
C7 C 0.19969(9) 0.9980(4) -0.0271(4) 0.0360(6) Uani 1 4 d . . .
C8 C 0.21501(9) 1.0602(4) 0.1578(4) 0.0394(6) Uani 1 4 d . . .
C9 C 0.26529(8) 1.0584(4) 0.2129(4) 0.0364(6) Uani 1 4 d . . .
C10 C 0.30257(8) 0.9964(3) 0.0833(3) 0.0301(5) Uani 1 4 d . . .
C11 C 0.28678(8) 0.9356(4) -0.1016(4) 0.0369(6) Uani 1 4 d . . .
C12 C 0.23629(9) 0.9370(4) -0.1560(4) 0.0378(6) Uani 1 4 d . . .
C13 C 0.35686(8) 0.9969(3) 0.1398(3) 0.0288(5) Uani 1 4 d . . .
C14 C 0.37525(9) 1.1263(4) 0.2778(3) 0.0357(6) Uani 1 4 d . . .
C15 C 0.42572(8) 1.1280(4) 0.3306(3) 0.0378(6) Uani 1 4 d . . .
C16 C 0.45930(9) 1.0017(4) 0.2439(3) 0.0364(6) Uani 1 4 d . . .
C17 C 0.44151(8) 0.8734(4) 0.1074(3) 0.0361(6) Uani 1 4 d . . .
C18 C 0.39105(8) 0.8693(4) 0.0549(3) 0.0332(6) Uani 1 4 d . . .
H3 H 0.31126 0.89217 -0.19277 0.0443 Uiso 1 4 calc R . .
H4 H 0.1904 1.10468 0.24786 0.0473 Uiso 1 4 calc R . .
H5 H 0.37958 0.77911 -0.03946 0.0398 Uiso 1 4 calc R . .
H8 H 0.11842 0.98745 0.17918 0.0494 Uiso 1 4 calc R . .
H9 H 0.49405 1.00381 0.27831 0.0436 Uiso 1 4 calc R . .
H10 H 0.46428 0.78597 0.04802 0.0434 Uiso 1 4 calc R . .
H11 H 0.27459 1.09996 0.34051 0.0436 Uiso 1 4 calc R . .
H12 H 0.35276 1.21506 0.33684 0.0428 Uiso 1 4 calc R . .
H13 H 0.22682 0.89545 -0.2834 0.0454 Uiso 1 4 calc R . .
H14 H 0.4374 1.21609 0.42667 0.0453 Uiso 1 4 calc R . .
H17 H 0.03881 0.87919 0.27901 0.0535 Uiso 1 4 calc R . .
H18 H 0.0481 1.12503 -0.2541 0.0549 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
N20 C6 1.137(3) yes . .
C1 C2 1.396(4) yes . .
C1 C3 1.386(4) yes . .
C1 C4 1.467(3) yes . .
C2 C3 1.379(3) yes . 3_575
C4 C5 1.335(3) yes . .
C5 C6 1.446(4) yes . .
C5 C7 1.491(3) yes . .
C7 C8 1.394(3) yes . .
C7 C12 1.379(3) yes . .
C8 C9 1.383(3) yes . .
C9 C10 1.397(3) yes . .
C10 C11 1.395(3) yes . .
C10 C13 1.488(3) yes . .
C11 C12 1.387(3) yes . .
C13 C14 1.392(3) yes . .
C13 C18 1.397(3) yes . .
C14 C15 1.384(3) yes . .
C15 C16 1.386(3) yes . .
C16 C17 1.374(3) yes . .
C17 C18 1.384(3) yes . .
C2 H18 0.950 no . .
C3 H17 0.950 no . .
C4 H8 0.950 no . .
C8 H4 0.950 no . .
C9 H11 0.950 no . .
C11 H3 0.950 no . .
C12 H13 0.950 no . .
C14 H12 0.950 no . .
C15 H14 0.950 no . .
C16 H9 0.950 no . .
C17 H10 0.950 no . .
C18 H5 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C2 C1 C3 117.3(2) yes . . .
C2 C1 C4 125.7(2) yes . . .
C3 C1 C4 117.1(2) yes . . .
C1 C2 C3 121.0(2) yes . . 3_575
C1 C3 C2 121.8(2) yes . . 3_575
C1 C4 C5 129.7(2) yes . . .
C4 C5 C6 120.7(2) yes . . .
C4 C5 C7 122.9(2) yes . . .
C6 C5 C7 116.4(2) yes . . .
N20 C6 C5 176.2(2) yes . . .
C5 C7 C8 121.0(2) yes . . .
C5 C7 C12 121.0(2) yes . . .
C8 C7 C12 118.1(2) yes . . .
C7 C8 C9 121.4(2) yes . . .
C8 C9 C10 120.9(2) yes . . .
C9 C10 C11 117.2(2) yes . . .
C9 C10 C13 121.4(2) yes . . .
C11 C10 C13 121.5(2) yes . . .
C10 C11 C12 121.8(2) yes . . .
C7 C12 C11 120.7(2) yes . . .
C10 C13 C14 120.9(2) yes . . .
C10 C13 C18 121.3(2) yes . . .
C14 C13 C18 117.9(2) yes . . .
C13 C14 C15 121.2(2) yes . . .
C14 C15 C16 120.3(2) yes . . .
C15 C16 C17 118.9(2) yes . . .
C16 C17 C18 121.2(2) yes . . .
C13 C18 C17 120.5(2) yes . . .
C1 C2 H18 119.522 no . . .
C3 C2 H18 119.498 no 3_575 . .
C1 C3 H17 119.124 no . . .
C2 C3 H17 119.121 no 3_575 . .
C1 C4 H8 115.170 no . . .
C5 C4 H8 115.173 no . . .
C7 C8 H4 119.296 no . . .
C9 C8 H4 119.293 no . . .
C8 C9 H11 119.584 no . . .
C10 C9 H11 119.565 no . . .
C10 C11 H3 119.112 no . . .
C12 C11 H3 119.128 no . . .
C7 C12 H13 119.637 no . . .
C11 C12 H13 119.651 no . . .
C13 C14 H12 119.411 no . . .
C15 C14 H12 119.400 no . . .
C14 C15 H14 119.858 no . . .
C16 C15 H14 119.839 no . . .
C15 C16 H9 120.533 no . . .
C17 C16 H9 120.533 no . . .
C16 C17 H10 119.385 no . . .
C18 C17 H10 119.383 no . . .
C13 C18 H5 119.772 no . . .
C17 C18 H5 119.767 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C2 C1 C3 C2 1.1(4) no . . . 3_575
C3 C1 C2 C3 -1.1(4) no . . . 3_575
C2 C1 C4 C5 -23.2(4) no . . . .
C4 C1 C2 C3 -179.5(2) no . . . 3_575
C3 C1 C4 C5 158.4(2) no . . . .
C4 C1 C3 C2 179.6(2) no . . . 3_575
C1 C2 C3 C1 1.1(4) no . . 3_575 3_575
C1 C4 C5 C6 -4.0(4) no . . . .
C1 C4 C5 C7 178.4(2) no . . . .
C4 C5 C7 C8 -23.1(4) no . . . .
C4 C5 C7 C12 157.4(2) no . . . .
C6 C5 C7 C8 159.2(2) no . . . .
C6 C5 C7 C12 -20.3(3) no . . . .
C5 C7 C8 C9 179.5(2) no . . . .
C5 C7 C12 C11 -179.7(2) no . . . .
C8 C7 C12 C11 0.8(4) no . . . .
C12 C7 C8 C9 -1.0(4) no . . . .
C7 C8 C9 C10 0.9(4) no . . . .
C8 C9 C10 C11 -0.5(3) no . . . .
C8 C9 C10 C13 179.0(2) no . . . .
C9 C10 C11 C12 0.2(3) no . . . .
C9 C10 C13 C14 -27.6(3) no . . . .
C9 C10 C13 C18 153.1(2) no . . . .
C11 C10 C13 C14 151.9(2) no . . . .
C11 C10 C13 C18 -27.5(3) no . . . .
C13 C10 C11 C12 -179.22(19) no . . . .
C10 C11 C12 C7 -0.4(4) no . . . .
C10 C13 C14 C15 -179.80(19) no . . . .
C10 C13 C18 C17 179.19(18) no . . . .
C14 C13 C18 C17 -0.2(3) no . . . .
C18 C13 C14 C15 -0.4(3) no . . . .
C13 C14 C15 C16 1.0(4) no . . . .
C14 C15 C16 C17 -1.0(3) no . . . .
C15 C16 C17 C18 0.4(4) no . . . .
C16 C17 C18 C13 0.2(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
N20 C2 3.432(3) no . .
N20 C4 3.483(3) no . .
N20 C7 3.480(3) no . .
N20 C12 3.529(3) no . .
C1 C1 2.827(3) no . 3_575
C1 C6 3.012(3) no . .
C2 C2 2.752(4) no . 3_575
C2 C5 3.164(3) no . .
C2 C6 3.018(3) no . .
C3 C3 2.742(4) no . 3_575
C4 C8 2.970(3) no . .
C6 C12 2.879(3) no . .
C7 C10 2.826(3) no . .
C8 C11 2.744(3) no . .
C9 C12 2.764(3) no . .
C9 C14 2.984(3) no . .
C11 C18 2.996(3) no . .
C13 C16 2.804(3) no . .
C14 C17 2.749(3) no . .
C15 C18 2.762(3) no . .
N20 C4 3.435(3) no . 1_554
N20 C4 3.456(4) no . 4_564
N20 C5 3.576(4) no . 4_564
N20 C8 3.517(3) no . 1_554
C4 N20 3.435(3) no . 1_556
C4 N20 3.456(4) no . 4_565
C5 N20 3.576(4) no . 4_565
C8 N20 3.517(3) no . 1_556
N20 H13 2.9326 no . .
N20 H18 2.7116 no . .
C1 H17 3.2654 no . 3_575
C1 H18 3.2646 no . 3_575
C2 H8 3.3209 no . .
C2 H17 3.2372 no . .
C3 H8 2.5587 no . .
C3 H18 3.2379 no . .
C4 H4 2.6901 no . .
C4 H17 2.5605 no . .
C4 H18 2.7440 no . .
C5 H4 2.6640 no . .
C5 H13 2.6549 no . .
C5 H18 2.9565 no . .
C6 H8 3.2486 no . .
C6 H13 2.5463 no . .
C6 H18 2.4728 no . .
C7 H3 3.2540 no . .
C7 H8 2.5781 no . .
C7 H11 3.2733 no . .
C8 H8 2.6140 no . .
C8 H13 3.2406 no . .
C9 H3 3.2442 no . .
C9 H12 2.6962 no . .
C10 H4 3.2695 no . .
C10 H5 2.6786 no . .
C10 H12 2.6601 no . .
C10 H13 3.2812 no . .
C11 H5 2.7227 no . .
C11 H11 3.2466 no . .
C12 H4 3.2363 no . .
C13 H3 2.6709 no . .
C13 H10 3.2665 no . .
C13 H11 2.6773 no . .
C13 H14 3.2718 no . .
C14 H5 3.2511 no . .
C14 H9 3.2620 no . .
C14 H11 2.7092 no . .
C15 H10 3.2354 no . .
C16 H5 3.2546 no . .
C16 H12 3.2555 no . .
C17 H14 3.2365 no . .
C18 H3 2.7084 no . .
C18 H9 3.2604 no . .
C18 H12 3.2496 no . .
H3 H5 2.2324 no . .
H3 H13 2.3199 no . .
H4 H8 2.1263 no . .
H4 H11 2.3174 no . .
H5 H10 2.3214 no . .
H8 H17 2.3440 no . .
H9 H10 2.3228 no . .
H9 H14 2.3411 no . .
H11 H12 2.2218 no . .
H12 H14 2.3235 no . .
H17 H18 2.3091 no . 3_575
N20 H4 2.7068 no . 1_554
N20 H4 3.5232 no . 4_574
N20 H8 2.4988 no . 1_554
N20 H8 3.4986 no . 4_564
N20 H17 3.0928 no . 1_554
C1 H17 3.1147 no . 4_564
C1 H18 3.0613 no . 4_575
C2 H17 3.2022 no . 4_564
C2 H18 3.4636 no . 4_575
C3 H17 3.5697 no . 2_555
C3 H17 3.4187 no . 4_564
C3 H18 3.2325 no . 4_575
C4 H18 3.3803 no . 4_575
C5 H4 3.2224 no . 4_574
C6 H4 3.5568 no . 1_554
C6 H4 3.1563 no . 4_574
C6 H8 3.4130 no . 4_564
C7 H4 3.1772 no . 4_574
C7 H11 3.5534 no . 4_574
C7 H13 3.2874 no . 4_565
C8 H11 3.5812 no . 4_574
C8 H13 3.2176 no . 4_565
C9 H3 3.4304 no . 4_565
C9 H11 3.4937 no . 4_574
C9 H13 3.3253 no . 4_565
C10 H3 3.1195 no . 4_565
C10 H11 3.3486 no . 4_574
C10 H12 2.9435 no . 4_574
C10 H13 3.5123 no . 4_565
C11 H11 3.2781 no . 4_574
C11 H12 3.0284 no . 4_574
C11 H13 3.5496 no . 4_565
C12 H4 3.4811 no . 4_574
C12 H11 3.3846 no . 4_574
C12 H13 3.4520 no . 4_565
C13 H3 3.1838 no . 4_565
C13 H5 2.9760 no . 4_565
C13 H12 2.8853 no . 4_574
C13 H14 3.2709 no . 4_574
C14 H5 3.0921 no . 4_565
C14 H12 3.2613 no . 4_574
C14 H14 3.1138 no . 4_574
C15 H5 3.2167 no . 4_565
C15 H9 3.4571 no . 2_655
C15 H9 3.5303 no . 3_676
C15 H10 3.2223 no . 2_655
C15 H10 3.4017 no . 4_565
C15 H14 2.9820 no . 4_574
C16 H5 3.2413 no . 4_565
C16 H9 3.4857 no . 3_676
C16 H10 3.1671 no . 2_655
C16 H10 3.2083 no . 3_675
C16 H10 2.8901 no . 4_565
C16 H14 3.5830 no . 2_645
C16 H14 2.9824 no . 4_574
C17 H5 3.1088 no . 4_565
C17 H9 3.1875 no . 2_645
C17 H9 3.2584 no . 3_675
C17 H10 3.2621 no . 4_565
C17 H14 3.4000 no . 2_645
C17 H14 3.1188 no . 4_574
C18 H3 3.2844 no . 4_565
C18 H5 2.9735 no . 4_565
C18 H12 3.4114 no . 4_574
C18 H14 3.2619 no . 4_574
H3 C9 3.4304 no . 4_564
H3 C10 3.1195 no . 4_564
H3 C13 3.1838 no . 4_564
H3 C18 3.2844 no . 4_564
H3 H5 3.2151 no . 4_564
H3 H11 3.5740 no . 4_564
H3 H12 2.9580 no . 4_574
H4 N20 2.7068 no . 1_556
H4 N20 3.5232 no . 4_575
H4 C5 3.2224 no . 4_575
H4 C6 3.5568 no . 1_556
H4 C6 3.1563 no . 4_575
H4 C7 3.1772 no . 4_575
H4 C12 3.4811 no . 4_575
H5 C13 2.9760 no . 4_564
H5 C14 3.0921 no . 4_564
H5 C15 3.2167 no . 4_564
H5 C16 3.2413 no . 4_564
H5 C17 3.1088 no . 4_564
H5 C18 2.9735 no . 4_564
H5 H3 3.2151 no . 4_565
H5 H5 3.4386 no . 4_564
H5 H5 3.4386 no . 4_565
H8 N20 2.4988 no . 1_556
H8 N20 3.4986 no . 4_565
H8 C6 3.4130 no . 4_565
H8 H18 3.3147 no . 4_575
H9 C15 3.4571 no . 2_645
H9 C15 3.5303 no . 3_676
H9 C16 3.4857 no . 3_676
H9 C17 3.1875 no . 2_655
H9 C17 3.2584 no . 3_675
H9 H9 3.5222 no . 2_645
H9 H9 3.5222 no . 2_655
H9 H9 3.0438 no . 3_676
H9 H10 2.5473 no . 2_655
H9 H10 2.8897 no . 3_675
H9 H10 2.8473 no . 4_565
H9 H14 3.0497 no . 2_645
H9 H14 3.1125 no . 3_676
H9 H14 3.4370 no . 4_574
H10 C15 3.2223 no . 2_645
H10 C15 3.4017 no . 4_564
H10 C16 3.1671 no . 2_645
H10 C16 3.2083 no . 3_675
H10 C16 2.8901 no . 4_564
H10 C17 3.2621 no . 4_564
H10 H9 2.5473 no . 2_645
H10 H9 2.8897 no . 3_675
H10 H9 2.8473 no . 4_564
H10 H10 3.5961 no . 3_675
H10 H10 3.4512 no . 4_564
H10 H10 3.4512 no . 4_565
H10 H14 2.6558 no . 2_645
H11 C7 3.5534 no . 4_575
H11 C8 3.5812 no . 4_575
H11 C9 3.4937 no . 4_575
H11 C10 3.3486 no . 4_575
H11 C11 3.2781 no . 4_575
H11 C12 3.3846 no . 4_575
H11 H3 3.5740 no . 4_565
H11 H13 3.2021 no . 1_556
H12 C10 2.9435 no . 4_575
H12 C11 3.0284 no . 4_575
H12 C13 2.8853 no . 4_575
H12 C14 3.2613 no . 4_575
H12 C18 3.4114 no . 4_575
H12 H3 2.9580 no . 4_575
H12 H12 3.4492 no . 4_574
H12 H12 3.4492 no . 4_575
H13 C7 3.2874 no . 4_564
H13 C8 3.2176 no . 4_564
H13 C9 3.3253 no . 4_564
H13 C10 3.5123 no . 4_564
H13 C11 3.5496 no . 4_564
H13 C12 3.4520 no . 4_564
H13 H11 3.2021 no . 1_554
H14 C13 3.2709 no . 4_575
H14 C14 3.1138 no . 4_575
H14 C15 2.9820 no . 4_575
H14 C16 3.5830 no . 2_655
H14 C16 2.9824 no . 4_575
H14 C17 3.4000 no . 2_655
H14 C17 3.1188 no . 4_575
H14 C18 3.2619 no . 4_575
H14 H9 3.0497 no . 2_655
H14 H9 3.1125 no . 3_676
H14 H9 3.4370 no . 4_575
H14 H10 2.6558 no . 2_655
H14 H14 3.4472 no . 4_574
H14 H14 3.4472 no . 4_575
H17 N20 3.0928 no . 1_556
H17 C1 3.1147 no . 4_565
H17 C2 3.2022 no . 4_565
H17 C3 3.5697 no . 2_545
H17 C3 3.4187 no . 4_565
H17 H18 3.5319 no . 4_565
H17 H18 3.4733 no . 4_575
H18 C1 3.0613 no . 4_574
H18 C2 3.4636 no . 4_574
H18 C3 3.2325 no . 4_574
H18 C4 3.3803 no . 4_574
H18 H8 3.3147 no . 4_574
H18 H17 3.5319 no . 4_564
H18 H17 3.4733 no . 4_574

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



####################################################################### 
# 
# 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_Compound_2b
_database_code_depnum_ccdc_archive 'CCDC 2034948'
loop_
_audit_author_name
_audit_author_address
'Masashi Mamada'
;Kyushu University
Japan
;
_audit_update_record             
;
2020-10-01 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C36 H24 N2'
_chemical_formula_moiety         'C36 H24 N2'
_chemical_formula_weight         484.60
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   26.029(7)
_cell_length_b                   6.7825(15)
_cell_length_c                   7.1139(17)
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.398(7)
_cell_angle_gamma                90.0000
_cell_volume                     1245.4(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4601
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      30.47
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508.00
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_T_max  0.996

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.222
_diffrn_reflns_number            10610
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         3.105
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2835
_reflns_number_gt                2492
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.1599
_refine_ls_wR_factor_gt          0.1546
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2835
_refine_ls_number_parameters     172
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0615P)²+1.0200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.62338(7) 0.4721(3) 0.9280(3) 0.0315(4) Uani 1 4 d . . .
C1 C 0.55112(7) 0.0477(3) 0.9723(3) 0.0221(4) Uani 1 4 d . . .
C2 C 0.53930(7) -0.1355(3) 1.0456(3) 0.0246(4) Uani 1 4 d . . .
C3 C 0.51113(7) 0.1829(3) 0.9280(3) 0.0243(4) Uani 1 4 d . . .
C4 C 0.60493(7) 0.0987(3) 0.9411(3) 0.0209(4) Uani 1 4 d . . .
C5 C 0.61669(7) 0.3060(3) 0.9339(3) 0.0207(4) Uani 1 4 d . . .
C6 C 0.64067(7) -0.0384(3) 0.9136(3) 0.0229(4) Uani 1 4 d . . .
C7 C 0.69501(7) -0.0148(3) 0.8823(3) 0.0214(4) Uani 1 4 d . . .
C8 C 0.71722(7) -0.1728(3) 0.7968(3) 0.0236(4) Uani 1 4 d . . .
C9 C 0.76809(7) -0.1670(3) 0.7612(3) 0.0212(4) Uani 1 4 d . . .
C10 C 0.79939(6) -0.0032(3) 0.8135(3) 0.0186(4) Uani 1 4 d . . .
C11 C 0.77749(7) 0.1538(3) 0.9021(3) 0.0226(4) Uani 1 4 d . . .
C12 C 0.72620(7) 0.1496(3) 0.9364(3) 0.0236(4) Uani 1 4 d . . .
C13 C 0.85448(7) 0.0003(3) 0.7800(3) 0.0184(4) Uani 1 4 d . . .
C14 C 0.87077(7) -0.1041(3) 0.6283(3) 0.0220(4) Uani 1 4 d . . .
C15 C 0.92237(7) -0.1048(3) 0.5975(3) 0.0251(4) Uani 1 4 d . . .
C16 C 0.95888(7) -0.0001(3) 0.7170(3) 0.0237(4) Uani 1 4 d . . .
C17 C 0.94337(7) 0.1058(3) 0.8664(3) 0.0230(4) Uani 1 4 d . . .
C18 C 0.89177(7) 0.1059(3) 0.8982(3) 0.0204(4) Uani 1 4 d . . .
H2 H 0.56617 -0.22898 1.07786 0.0295 Uiso 1 4 calc R . .
H3 H 0.51844 0.30875 0.87929 0.0291 Uiso 1 4 calc R . .
H6 H 0.62889 -0.17092 0.9146 0.0274 Uiso 1 4 calc R . .
H8 H 0.69694 -0.28665 0.76219 0.0283 Uiso 1 4 calc R . .
H9 H 0.78204 -0.27572 0.7005 0.0254 Uiso 1 4 calc R . .
H11 H 0.79813 0.26605 0.93963 0.0271 Uiso 1 4 calc R . .
H12 H 0.71215 0.25837 0.99672 0.0283 Uiso 1 4 calc R . .
H14 H 0.84606 -0.1757 0.54498 0.0264 Uiso 1 4 calc R . .
H15 H 0.93269 -0.17708 0.49424 0.0301 Uiso 1 4 calc R . .
H16 H 0.99424 -0.00096 0.69664 0.0285 Uiso 1 4 calc R . .
H17 H 0.96819 0.17903 0.94775 0.0276 Uiso 1 4 calc R . .
H18 H 0.88174 0.17865 1.00163 0.0245 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
N1 C5 1.142(3) yes . .
C1 C2 1.397(3) yes . .
C1 C3 1.392(3) yes . .
C1 C4 1.487(3) yes . .
C2 C3 1.387(3) yes . 3_657
C4 C5 1.441(3) yes . .
C4 C6 1.347(3) yes . .
C6 C7 1.469(3) yes . .
C7 C8 1.394(3) yes . .
C7 C12 1.403(3) yes . .
C8 C9 1.380(3) yes . .
C9 C10 1.400(3) yes . .
C10 C11 1.396(3) yes . .
C10 C13 1.484(3) yes . .
C11 C12 1.388(3) yes . .
C13 C14 1.401(3) yes . .
C13 C18 1.397(2) yes . .
C14 C15 1.388(3) yes . .
C15 C16 1.387(3) yes . .
C16 C17 1.385(3) yes . .
C17 C18 1.390(3) yes . .
C2 H2 0.950 no . .
C3 H3 0.950 no . .
C6 H6 0.950 no . .
C8 H8 0.950 no . .
C9 H9 0.950 no . .
C11 H11 0.950 no . .
C12 H12 0.950 no . .
C14 H14 0.950 no . .
C15 H15 0.950 no . .
C16 H16 0.950 no . .
C17 H17 0.950 no . .
C18 H18 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C2 C1 C3 118.42(17) yes . . .
C2 C1 C4 121.31(17) yes . . .
C3 C1 C4 120.27(18) yes . . .
C1 C2 C3 120.93(18) yes . . 3_657
C1 C3 C2 120.64(19) yes . . 3_657
C1 C4 C5 116.15(17) yes . . .
C1 C4 C6 122.85(18) yes . . .
C5 C4 C6 120.95(18) yes . . .
N1 C5 C4 176.5(2) yes . . .
C4 C6 C7 130.03(18) yes . . .
C6 C7 C8 116.36(17) yes . . .
C6 C7 C12 125.42(18) yes . . .
C8 C7 C12 118.19(17) yes . . .
C7 C8 C9 121.32(18) yes . . .
C8 C9 C10 120.87(18) yes . . .
C9 C10 C11 117.91(16) yes . . .
C9 C10 C13 120.75(16) yes . . .
C11 C10 C13 121.33(16) yes . . .
C10 C11 C12 121.44(18) yes . . .
C7 C12 C11 120.25(19) yes . . .
C10 C13 C14 120.70(16) yes . . .
C10 C13 C18 121.46(17) yes . . .
C14 C13 C18 117.84(17) yes . . .
C13 C14 C15 121.20(17) yes . . .
C14 C15 C16 120.14(19) yes . . .
C15 C16 C17 119.45(18) yes . . .
C16 C17 C18 120.54(17) yes . . .
C13 C18 C17 120.83(18) yes . . .
C1 C2 H2 119.539 no . . .
C3 C2 H2 119.527 no 3_657 . .
C1 C3 H3 119.696 no . . .
C2 C3 H3 119.664 no 3_657 . .
C4 C6 H6 114.981 no . . .
C7 C6 H6 114.984 no . . .
C7 C8 H8 119.352 no . . .
C9 C8 H8 119.326 no . . .
C8 C9 H9 119.556 no . . .
C10 C9 H9 119.572 no . . .
C10 C11 H11 119.293 no . . .
C12 C11 H11 119.270 no . . .
C7 C12 H12 119.864 no . . .
C11 C12 H12 119.887 no . . .
C13 C14 H14 119.399 no . . .
C15 C14 H14 119.399 no . . .
C14 C15 H15 119.944 no . . .
C16 C15 H15 119.920 no . . .
C15 C16 H16 120.276 no . . .
C17 C16 H16 120.272 no . . .
C16 C17 H17 119.729 no . . .
C18 C17 H17 119.735 no . . .
C13 C18 H18 119.584 no . . .
C17 C18 H18 119.587 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C2 C1 C3 C2 -0.7(3) no . . . 3_657
C3 C1 C2 C3 0.7(3) no . . . 3_657
C2 C1 C4 C5 -157.76(16) no . . . .
C2 C1 C4 C6 24.7(3) no . . . .
C4 C1 C2 C3 -179.14(15) no . . . 3_657
C3 C1 C4 C5 22.4(2) no . . . .
C3 C1 C4 C6 -155.12(17) no . . . .
C4 C1 C3 C2 179.15(15) no . . . 3_657
C1 C2 C3 C1 -0.7(3) no . . 3_657 3_657
C1 C4 C6 C7 -179.52(15) no . . . .
C5 C4 C6 C7 3.0(3) no . . . .
C4 C6 C7 C8 -159.15(18) no . . . .
C4 C6 C7 C12 22.9(3) no . . . .
C6 C7 C8 C9 -179.74(15) no . . . .
C6 C7 C12 C11 178.91(16) no . . . .
C8 C7 C12 C11 0.9(3) no . . . .
C12 C7 C8 C9 -1.6(3) no . . . .
C7 C8 C9 C10 1.2(3) no . . . .
C8 C9 C10 C11 -0.1(3) no . . . .
C8 C9 C10 C13 178.29(15) no . . . .
C9 C10 C11 C12 -0.5(3) no . . . .
C9 C10 C13 C14 29.5(2) no . . . .
C9 C10 C13 C18 -150.12(16) no . . . .
C11 C10 C13 C14 -152.12(16) no . . . .
C11 C10 C13 C18 28.3(2) no . . . .
C13 C10 C11 C12 -178.93(14) no . . . .
C10 C11 C12 C7 0.1(3) no . . . .
C10 C13 C14 C15 -178.87(15) no . . . .
C10 C13 C18 C17 179.22(15) no . . . .
C14 C13 C18 C17 -0.4(3) no . . . .
C18 C13 C14 C15 0.8(3) no . . . .
C13 C14 C15 C16 -0.4(3) no . . . .
C14 C15 C16 C17 -0.4(3) no . . . .
C15 C16 C17 C18 0.7(3) no . . . .
C16 C17 C18 C13 -0.3(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
N1 C1 3.475(3) no . .
N1 C3 3.519(3) no . .
N1 C6 3.495(3) no . .
N1 C12 3.451(3) no . .
C1 C1 2.815(3) no . 3_657
C2 C2 2.765(3) no . 3_657
C2 C6 2.986(3) no . .
C3 C3 2.773(3) no . 3_657
C3 C5 2.867(3) no . .
C4 C12 3.180(3) no . .
C5 C7 3.036(3) no . .
C5 C12 3.039(3) no . .
C7 C10 2.823(3) no . .
C8 C11 2.762(3) no . .
C9 C12 2.775(3) no . .
C9 C14 2.978(3) no . .
C11 C18 2.996(3) no . .
C13 C16 2.810(3) no . .
C14 C17 2.765(3) no . .
C15 C18 2.773(3) no . .
N1 C1 3.535(3) no . 4_554
N1 C2 3.448(3) no . 4_554
N1 C4 3.469(3) no . 4_554
N1 C6 3.354(3) no . 1_565
N1 C6 3.455(3) no . 4_555
N1 C7 3.529(3) no . 4_555
C1 N1 3.535(3) no . 4_555
C2 N1 3.448(3) no . 4_555
C4 N1 3.469(3) no . 4_555
C4 C5 3.539(3) no . 4_555
C5 C4 3.539(3) no . 4_554
C6 N1 3.354(3) no . 1_545
C6 N1 3.455(3) no . 4_554
C7 N1 3.529(3) no . 4_554
C8 C9 3.567(3) no . 4_545
C9 C8 3.567(3) no . 4_544
C17 C17 3.595(3) no . 3_757
N1 H3 2.9265 no . .
N1 H12 2.7181 no . .
C1 H2 3.2679 no . 3_657
C1 H3 3.2755 no . 3_657
C1 H6 2.5843 no . .
C2 H3 3.2571 no . .
C2 H6 2.6313 no . .
C3 H2 3.2555 no . .
C4 H2 2.6751 no . .
C4 H3 2.6526 no . .
C4 H12 2.9722 no . .
C5 H3 2.5368 no . .
C5 H6 3.2545 no . .
C5 H12 2.4883 no . .
C6 H2 2.7166 no . .
C6 H8 2.5587 no . .
C6 H12 2.7531 no . .
C7 H9 3.2698 no . .
C7 H11 3.2737 no . .
C8 H6 2.5466 no . .
C8 H12 3.2619 no . .
C9 H11 3.2548 no . .
C9 H14 2.7006 no . .
C10 H8 3.2696 no . .
C10 H12 3.2809 no . .
C10 H14 2.6630 no . .
C10 H18 2.6772 no . .
C11 H9 3.2560 no . .
C11 H18 2.7200 no . .
C12 H6 3.3262 no . .
C12 H8 3.2600 no . .
C13 H9 2.6653 no . .
C13 H11 2.6684 no . .
C13 H15 3.2845 no . .
C13 H17 3.2780 no . .
C14 H9 2.6942 no . .
C14 H16 3.2637 no . .
C14 H18 3.2586 no . .
C15 H17 3.2514 no . .
C16 H14 3.2580 no . .
C16 H18 3.2631 no . .
C17 H15 3.2525 no . .
C18 H11 2.7189 no . .
C18 H14 3.2569 no . .
C18 H16 3.2680 no . .
H2 H3 2.3256 no . 3_657
H2 H6 2.1581 no . .
H6 H8 2.3289 no . .
H8 H9 2.3141 no . .
H9 H14 2.2217 no . .
H11 H12 2.3260 no . .
H11 H18 2.2439 no . .
H14 H15 2.3290 no . .
H15 H16 2.3394 no . .
H16 H17 2.3352 no . .
H17 H18 2.3307 no . .
N1 H2 2.8059 no . 1_565
N1 H2 3.2408 no . 4_554
N1 H6 2.4281 no . 1_565
N1 H8 2.8839 no . 1_565
N1 H8 3.5633 no . 4_555
C1 H3 3.3158 no . 2_646
C1 H3 3.2692 no . 4_555
C2 H3 3.2200 no . 2_646
C2 H3 3.3426 no . 4_555
C2 H6 3.5321 no . 4_545
C3 H3 3.3730 no . 2_646
C3 H3 3.1918 no . 4_555
C5 H6 3.5665 no . 1_565
C6 H2 3.2805 no . 4_544
C6 H8 2.9609 no . 4_545
C7 H8 3.0138 no . 4_545
C7 H9 3.3095 no . 4_545
C7 H12 3.3264 no . 4_554
C8 H6 3.4916 no . 4_544
C8 H8 3.4304 no . 4_545
C8 H9 3.1575 no . 4_545
C8 H12 3.5214 no . 4_554
C9 H9 3.1233 no . 4_545
C9 H12 3.5549 no . 4_554
C9 H14 2.8768 no . 4_545
C10 H9 3.2175 no . 4_545
C10 H11 3.1048 no . 4_554
C10 H12 3.4168 no . 4_554
C10 H14 2.9010 no . 4_545
C11 H9 3.3217 no . 4_545
C11 H11 3.4439 no . 4_554
C11 H12 3.2091 no . 4_554
C12 H8 3.5307 no . 4_545
C12 H9 3.3718 no . 4_545
C12 H12 3.1642 no . 4_554
C13 H11 3.1001 no . 4_554
C13 H14 2.9248 no . 4_545
C13 H15 3.2362 no . 4_545
C13 H18 3.0869 no . 4_554
C14 H11 3.1590 no . 4_554
C14 H14 3.4530 no . 4_545
C14 H15 3.2400 no . 4_545
C14 H18 3.0473 no . 4_554
C15 H15 3.1677 no . 4_545
C15 H16 3.2820 no . 3_756
C15 H17 3.2564 no . 2_746
C15 H17 3.3498 no . 4_554
C15 H18 3.1224 no . 4_554
C16 H15 3.5720 no . 3_756
C16 H15 3.0816 no . 4_545
C16 H16 3.3275 no . 3_756
C16 H17 3.2074 no . 2_746
C16 H17 3.0982 no . 3_757
C16 H17 2.9305 no . 4_554
C16 H18 3.2154 no . 4_554
C17 H15 3.5685 no . 2_756
C17 H15 3.0703 no . 4_545
C17 H16 3.1840 no . 2_756
C17 H16 3.3922 no . 3_757
C17 H17 3.1618 no . 3_757
C17 H17 3.4512 no . 4_554
C17 H18 3.2204 no . 4_554
C18 H14 3.3674 no . 4_545
C18 H15 3.1421 no . 4_545
C18 H18 3.1580 no . 4_554
H2 N1 2.8059 no . 1_545
H2 N1 3.2408 no . 4_555
H2 C6 3.2805 no . 4_545
H2 H2 3.5684 no . 4_544
H2 H2 3.5684 no . 4_545
H2 H3 3.5941 no . 1_545
H2 H6 2.8031 no . 4_545
H2 H8 3.4881 no . 4_545
H3 C1 3.3158 no . 2_656
H3 C1 3.2692 no . 4_554
H3 C2 3.2200 no . 2_656
H3 C2 3.3426 no . 4_554
H3 C3 3.3730 no . 2_656
H3 C3 3.1918 no . 4_554
H3 H2 3.5941 no . 1_565
H3 H3 3.3206 no . 3_667
H6 N1 2.4281 no . 1_545
H6 C2 3.5321 no . 4_544
H6 C5 3.5665 no . 1_545
H6 C8 3.4916 no . 4_545
H6 H2 2.8031 no . 4_544
H6 H8 2.8647 no . 4_545
H8 N1 2.8839 no . 1_545
H8 N1 3.5633 no . 4_554
H8 C6 2.9609 no . 4_544
H8 C7 3.0138 no . 4_544
H8 C8 3.4304 no . 4_544
H8 C12 3.5307 no . 4_544
H8 H2 3.4881 no . 4_544
H8 H6 2.8647 no . 4_544
H8 H8 3.5915 no . 4_544
H8 H8 3.5915 no . 4_545
H8 H12 3.5061 no . 1_545
H9 C7 3.3095 no . 4_544
H9 C8 3.1575 no . 4_544
H9 C9 3.1233 no . 4_544
H9 C10 3.2175 no . 4_544
H9 C11 3.3217 no . 4_544
H9 C12 3.3718 no . 4_544
H9 H9 3.5740 no . 4_544
H9 H9 3.5740 no . 4_545
H9 H11 3.5419 no . 1_545
H9 H14 2.7998 no . 4_545
H11 C10 3.1048 no . 4_555
H11 C11 3.4439 no . 4_555
H11 C13 3.1001 no . 4_555
H11 C14 3.1590 no . 4_555
H11 H9 3.5419 no . 1_565
H11 H11 3.5636 no . 4_554
H11 H11 3.5636 no . 4_555
H11 H14 3.0979 no . 4_555
H12 C7 3.3264 no . 4_555
H12 C8 3.5214 no . 4_555
H12 C9 3.5549 no . 4_555
H12 C10 3.4168 no . 4_555
H12 C11 3.2091 no . 4_555
H12 C12 3.1642 no . 4_555
H12 H8 3.5061 no . 1_565
H12 H12 3.5588 no . 4_554
H12 H12 3.5588 no . 4_555
H14 C9 2.8768 no . 4_544
H14 C10 2.9010 no . 4_544
H14 C13 2.9248 no . 4_544
H14 C14 3.4530 no . 4_544
H14 C18 3.3674 no . 4_544
H14 H9 2.7998 no . 4_544
H14 H11 3.0979 no . 4_554
H14 H18 3.5592 no . 4_544
H14 H18 3.5209 no . 4_554
H15 C13 3.2362 no . 4_544
H15 C14 3.2400 no . 4_544
H15 C15 3.1677 no . 4_544
H15 C16 3.5720 no . 3_756
H15 C16 3.0816 no . 4_544
H15 C17 3.5685 no . 2_746
H15 C17 3.0703 no . 4_544
H15 C18 3.1421 no . 4_544
H15 H16 3.4931 no . 2_746
H15 H16 2.7540 no . 3_756
H15 H16 3.5624 no . 4_544
H15 H17 2.7395 no . 2_746
H15 H17 3.5542 no . 4_544
H15 H17 3.5289 no . 4_554
H16 C15 3.2820 no . 3_756
H16 C16 3.3275 no . 3_756
H16 C17 3.1840 no . 2_746
H16 C17 3.3922 no . 3_757
H16 H15 3.4931 no . 2_756
H16 H15 2.7540 no . 3_756
H16 H15 3.5624 no . 4_545
H16 H16 3.4797 no . 2_746
H16 H16 3.4797 no . 2_756
H16 H16 2.8519 no . 3_756
H16 H17 2.6422 no . 2_746
H16 H17 2.8597 no . 3_757
H16 H17 2.8378 no . 4_554
H17 C15 3.2564 no . 2_756
H17 C15 3.3498 no . 4_555
H17 C16 3.2074 no . 2_756
H17 C16 3.0982 no . 3_757
H17 C16 2.9305 no . 4_555
H17 C17 3.1618 no . 3_757
H17 C17 3.4512 no . 4_555
H17 H15 2.7395 no . 2_756
H17 H15 3.5542 no . 4_545
H17 H15 3.5289 no . 4_555
H17 H16 2.6422 no . 2_756
H17 H16 2.8597 no . 3_757
H17 H16 2.8378 no . 4_555
H17 H17 2.9792 no . 3_757
H18 C13 3.0869 no . 4_555
H18 C14 3.0473 no . 4_555
H18 C15 3.1224 no . 4_555
H18 C16 3.2154 no . 4_555
H18 C17 3.2204 no . 4_555
H18 C18 3.1580 no . 4_555
H18 H14 3.5592 no . 4_545
H18 H14 3.5209 no . 4_555

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



####################################################################### 
# 
# 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_Compound_3b
_database_code_depnum_ccdc_archive 'CCDC 2034952'
loop_
_audit_author_name
_audit_author_address
'Masashi Mamada'
;Kyushu University
Japan
;
_audit_update_record             
;
2020-10-01 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C32 H22 N2'
_chemical_formula_moiety         'C32 H22 N2'
_chemical_formula_weight         434.54
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   24.094(9)
_cell_length_b                   6.955(2)
_cell_length_c                   6.805(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.698(8)
_cell_angle_gamma                90.0000
_cell_volume                     1139.2(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2258
_cell_measurement_theta_min      4.02
_cell_measurement_theta_max      19.97
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456.00
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_T_max  0.987

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.222
_diffrn_reflns_number            10089
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.049
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2592
_reflns_number_gt                2382
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.1680
_refine_ls_wR_factor_gt          0.1646
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2592
_refine_ls_number_parameters     154
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0657P)²+0.8120P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.74435(7) 0.0083(3) 1.1798(2) 0.0333(4) Uani 1 4 d . . .
C1 C 0.99026(7) 0.0175(3) 0.5886(3) 0.0240(4) Uani 1 4 d . . .
C2 C 0.93204(7) 0.0057(3) 0.6425(3) 0.0226(4) Uani 1 4 d . . .
C3 C 0.91711(7) 0.0718(3) 0.8274(3) 0.0257(4) Uani 1 4 d . . .
C4 C 0.86244(7) 0.0700(3) 0.8832(3) 0.0244(4) Uani 1 4 d . . .
C5 C 0.82028(7) 0.0015(2) 0.7535(3) 0.0211(4) Uani 1 4 d . . .
C6 C 0.83488(7) -0.0699(3) 0.5700(3) 0.0233(4) Uani 1 4 d . . .
C7 C 0.88970(7) -0.0673(3) 0.5152(3) 0.0240(4) Uani 1 4 d . . .
C8 C 0.76101(7) 0.0022(2) 0.8062(3) 0.0203(4) Uani 1 4 d . . .
C9 C 0.75111(7) 0.0042(3) 1.0143(3) 0.0224(4) Uani 1 4 d . . .
C10 C 0.71796(7) 0.0096(2) 0.6729(3) 0.0210(4) Uani 1 4 d . . .
C11 C 0.65837(7) 0.0023(2) 0.7101(3) 0.0203(4) Uani 1 4 d . . .
C12 C 0.63687(7) -0.1098(3) 0.8589(3) 0.0237(4) Uani 1 4 d . . .
C13 C 0.58009(7) -0.1119(3) 0.8882(3) 0.0265(4) Uani 1 4 d . . .
C14 C 0.54398(7) -0.0022(3) 0.7692(3) 0.0254(4) Uani 1 4 d . . .
C15 C 0.56479(7) 0.1070(3) 0.6189(3) 0.0262(4) Uani 1 4 d . . .
C16 C 0.62129(7) 0.1082(3) 0.5878(3) 0.0242(4) Uani 1 4 d . . .
H1 H 1.01672 0.05355 0.68981 0.0288 Uiso 1 4 calc R . .
H3 H 0.94525 0.1192 0.91715 0.0308 Uiso 1 4 calc R . .
H4 H 0.85366 0.11549 1.00963 0.0293 Uiso 1 4 calc R . .
H6 H 0.80684 -0.12089 0.48203 0.0280 Uiso 1 4 calc R . .
H7 H 0.8986 -0.11546 0.38994 0.0289 Uiso 1 4 calc R . .
H10 H 0.72717 0.02094 0.53916 0.0252 Uiso 1 4 calc R . .
H12 H 0.66125 -0.18547 0.94089 0.0284 Uiso 1 4 calc R . .
H13 H 0.56598 -0.18851 0.99006 0.0318 Uiso 1 4 calc R . .
H14 H 0.50529 -0.00212 0.79049 0.0305 Uiso 1 4 calc R . .
H15 H 0.54018 0.18158 0.53667 0.0314 Uiso 1 4 calc R . .
H16 H 0.63495 0.18145 0.48264 0.0291 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
N1 C9 1.146(2) yes . .
C1 C1 1.337(3) yes . 3_756
C1 C2 1.469(2) yes . .
C2 C3 1.402(3) yes . .
C2 C7 1.402(2) yes . .
C3 C4 1.388(2) yes . .
C4 C5 1.398(2) yes . .
C5 C6 1.404(3) yes . .
C5 C8 1.489(2) yes . .
C6 C7 1.389(2) yes . .
C8 C9 1.447(3) yes . .
C8 C10 1.346(2) yes . .
C10 C11 1.470(2) yes . .
C11 C12 1.397(2) yes . .
C11 C16 1.401(2) yes . .
C12 C13 1.392(2) yes . .
C13 C14 1.389(3) yes . .
C14 C15 1.387(3) yes . .
C15 C16 1.388(2) yes . .
C1 H1 0.950 no . .
C3 H3 0.950 no . .
C4 H4 0.950 no . .
C6 H6 0.950 no . .
C7 H7 0.950 no . .
C10 H10 0.950 no . .
C12 H12 0.950 no . .
C13 H13 0.950 no . .
C14 H14 0.950 no . .
C15 H15 0.950 no . .
C16 H16 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 C1 C2 126.53(16) yes 3_756 . .
C1 C2 C3 119.62(15) yes . . .
C1 C2 C7 122.79(16) yes . . .
C3 C2 C7 117.59(16) yes . . .
C2 C3 C4 121.96(16) yes . . .
C3 C4 C5 120.10(17) yes . . .
C4 C5 C6 118.49(16) yes . . .
C4 C5 C8 121.60(16) yes . . .
C6 C5 C8 119.91(15) yes . . .
C5 C6 C7 121.01(16) yes . . .
C2 C7 C6 120.81(17) yes . . .
C5 C8 C9 116.09(14) yes . . .
C5 C8 C10 123.73(16) yes . . .
C9 C8 C10 120.11(16) yes . . .
N1 C9 C8 178.45(19) yes . . .
C8 C10 C11 127.60(16) yes . . .
C10 C11 C12 122.86(15) yes . . .
C10 C11 C16 118.69(15) yes . . .
C12 C11 C16 118.43(16) yes . . .
C11 C12 C13 120.67(16) yes . . .
C12 C13 C14 120.26(17) yes . . .
C13 C14 C15 119.52(16) yes . . .
C14 C15 C16 120.48(16) yes . . .
C11 C16 C15 120.60(17) yes . . .
C1 C1 H1 116.741 no 3_756 . .
C2 C1 H1 116.732 no . . .
C2 C3 H3 119.023 no . . .
C4 C3 H3 119.022 no . . .
C3 C4 H4 119.960 no . . .
C5 C4 H4 119.944 no . . .
C5 C6 H6 119.486 no . . .
C7 C6 H6 119.502 no . . .
C2 C7 H7 119.596 no . . .
C6 C7 H7 119.593 no . . .
C8 C10 H10 116.187 no . . .
C11 C10 H10 116.211 no . . .
C11 C12 H12 119.664 no . . .
C13 C12 H12 119.666 no . . .
C12 C13 H13 119.878 no . . .
C14 C13 H13 119.863 no . . .
C13 C14 H14 120.241 no . . .
C15 C14 H14 120.240 no . . .
C14 C15 H15 119.754 no . . .
C16 C15 H15 119.770 no . . .
C11 C16 H16 119.708 no . . .
C15 C16 H16 119.689 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 C1 C2 C3 -171.38(16) no 3_756 . . .
C1 C1 C2 C7 7.7(3) no 3_756 . . .
C2 C1 C1 C2 -180.00(15) no . . 3_756 3_756
C1 C2 C3 C4 177.78(15) no . . . .
C1 C2 C7 C6 -177.92(15) no . . . .
C3 C2 C7 C6 1.2(3) no . . . .
C7 C2 C3 C4 -1.4(3) no . . . .
C2 C3 C4 C5 -0.2(3) no . . . .
C3 C4 C5 C6 1.9(3) no . . . .
C3 C4 C5 C8 -178.37(15) no . . . .
C4 C5 C6 C7 -2.0(3) no . . . .
C4 C5 C8 C9 -23.2(2) no . . . .
C4 C5 C8 C10 153.73(16) no . . . .
C6 C5 C8 C9 156.57(14) no . . . .
C6 C5 C8 C10 -26.5(2) no . . . .
C8 C5 C6 C7 178.21(14) no . . . .
C5 C6 C7 C2 0.5(3) no . . . .
C5 C8 C10 C11 177.04(14) no . . . .
C9 C8 C10 C11 -6.2(3) no . . . .
C8 C10 C11 C12 -35.7(3) no . . . .
C8 C10 C11 C16 146.10(16) no . . . .
C10 C11 C12 C13 179.99(14) no . . . .
C10 C11 C16 C15 -179.31(14) no . . . .
C12 C11 C16 C15 2.4(2) no . . . .
C16 C11 C12 C13 -1.8(2) no . . . .
C11 C12 C13 C14 0.1(3) no . . . .
C12 C13 C14 C15 1.0(3) no . . . .
C13 C14 C15 C16 -0.4(3) no . . . .
C14 C15 C16 C11 -1.3(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
N1 C4 3.591(3) no . .
N1 C5 3.502(3) no . .
N1 C10 3.478(3) no . .
N1 C12 3.409(2) no . .
C1 C7 3.029(3) no . 3_756
C2 C5 2.831(3) no . .
C3 C6 2.764(3) no . .
C4 C7 2.787(3) no . .
C4 C9 2.903(3) no . .
C6 C10 2.986(3) no . .
C8 C12 3.128(3) no . .
C9 C11 2.974(2) no . .
C9 C12 3.008(3) no . .
C11 C14 2.804(3) no . .
C12 C15 2.773(3) no . .
C13 C16 2.774(3) no . .
N1 C6 3.400(2) no . 1_556
N1 C8 3.530(3) no . 4_555
N1 C10 3.445(3) no . 1_556
N1 C10 3.413(3) no . 4_555
C6 N1 3.400(2) no . 1_554
C8 N1 3.530(3) no . 4_554
C10 N1 3.445(3) no . 1_554
C10 N1 3.413(3) no . 4_554
N1 H4 3.0200 no . .
N1 H12 2.8568 no . .
C1 H3 2.6275 no . .
C1 H7 2.6979 no . .
C1 H7 2.7604 no . 3_756
C2 H1 2.6592 no . 3_756
C2 H4 3.2917 no . .
C2 H6 3.2799 no . .
C3 H1 2.6200 no . .
C3 H7 3.2608 no . .
C4 H6 3.2658 no . .
C5 H3 3.2651 no . .
C5 H7 3.2839 no . .
C5 H10 2.6213 no . .
C6 H4 3.2695 no . .
C6 H10 2.6697 no . .
C7 H1 3.3379 no . .
C7 H1 2.7085 no . 3_756
C7 H3 3.2573 no . .
C8 H4 2.6889 no . .
C8 H6 2.6547 no . .
C8 H12 2.9203 no . .
C9 H4 2.5908 no . .
C9 H10 3.2598 no . .
C9 H12 2.5645 no . .
C10 H6 2.7126 no . .
C10 H12 2.6961 no . .
C10 H16 2.6194 no . .
C11 H13 3.2781 no . .
C11 H15 3.2773 no . .
C12 H10 3.2772 no . .
C12 H14 3.2695 no . .
C12 H16 3.2636 no . .
C13 H15 3.2552 no . .
C14 H12 3.2654 no . .
C14 H16 3.2620 no . .
C15 H13 3.2555 no . .
C16 H10 2.6580 no . .
C16 H12 3.2641 no . .
C16 H14 3.2658 no . .
H1 H1 2.7717 no . 3_756
H1 H3 2.4121 no . .
H1 H7 2.1787 no . 3_756
H3 H4 2.3232 no . .
H6 H7 2.3265 no . .
H6 H10 2.2089 no . .
H10 H12 3.5308 no . .
H10 H16 2.5002 no . .
H12 H13 2.3353 no . .
H13 H14 2.3402 no . .
H14 H15 2.3366 no . .
H15 H16 2.3298 no . .
N1 H6 2.6482 no . 1_556
N1 H6 3.3954 no . 4_545
N1 H10 2.5011 no . 1_556
N1 H10 3.4312 no . 4_555
N1 H12 3.5415 no . 4_545
C1 H1 3.5691 no . 2_746
C1 H3 3.1774 no . 2_746
C1 H3 2.9672 no . 4_554
C2 H1 3.5476 no . 2_746
C2 H3 3.0504 no . 4_554
C2 H4 3.3413 no . 4_554
C2 H7 3.3137 no . 4_545
C3 H4 3.3812 no . 4_554
C3 H7 3.2362 no . 4_545
C4 H4 3.3526 no . 4_554
C4 H6 3.4773 no . 4_545
C4 H7 3.2794 no . 4_545
C5 H4 3.2596 no . 4_554
C5 H6 3.0949 no . 4_545
C5 H7 3.3863 no . 4_545
C6 H4 3.2222 no . 4_554
C6 H7 3.4014 no . 4_545
C7 H3 3.4688 no . 4_554
C7 H4 3.2597 no . 4_554
C7 H7 3.3716 no . 4_545
C8 H6 3.0919 no . 4_545
C9 H6 3.5055 no . 1_556
C9 H6 2.9981 no . 4_545
C9 H10 3.3582 no . 4_555
C9 H16 3.5499 no . 4_555
C10 H12 3.0396 no . 4_544
C11 H12 2.8684 no . 4_544
C11 H13 3.4126 no . 4_544
C11 H16 2.9491 no . 4_555
C12 H12 3.2589 no . 4_544
C12 H13 3.2833 no . 4_544
C12 H16 3.0974 no . 4_555
C13 H13 3.0493 no . 4_544
C13 H14 3.5838 no . 2_646
C13 H14 3.1725 no . 3_657
C13 H15 3.2958 no . 2_646
C13 H15 3.3156 no . 4_555
C13 H16 3.3230 no . 4_555
C14 H13 3.4458 no . 3_657
C14 H13 2.9342 no . 4_544
C14 H14 3.2750 no . 3_657
C14 H15 3.3085 no . 2_646
C14 H15 3.0986 no . 3_656
C14 H15 2.8833 no . 4_555
C14 H16 3.4050 no . 4_555
C15 H13 3.5043 no . 2_656
C15 H13 3.0405 no . 4_544
C15 H14 3.2743 no . 2_656
C15 H14 3.2715 no . 3_656
C15 H15 3.3607 no . 3_656
C15 H15 3.2795 no . 4_555
C15 H16 3.2796 no . 4_555
C16 H12 3.2652 no . 4_544
C16 H13 3.2642 no . 4_544
C16 H16 3.0637 no . 4_555
H1 C1 3.5691 no . 2_756
H1 C2 3.5476 no . 2_756
H1 H3 3.2495 no . 2_746
H1 H3 3.0343 no . 3_757
H1 H3 3.3598 no . 4_554
H3 C1 3.1774 no . 2_756
H3 C1 2.9672 no . 4_555
H3 C2 3.0504 no . 4_555
H3 C7 3.4688 no . 4_555
H3 H1 3.2495 no . 2_756
H3 H1 3.0343 no . 3_757
H3 H1 3.3598 no . 4_555
H3 H3 3.2713 no . 3_757
H4 C2 3.3413 no . 4_555
H4 C3 3.3812 no . 4_555
H4 C4 3.3526 no . 4_555
H4 C5 3.2596 no . 4_555
H4 C6 3.2222 no . 4_555
H4 C7 3.2597 no . 4_555
H4 H7 3.1917 no . 1_556
H6 N1 2.6482 no . 1_554
H6 N1 3.3954 no . 4_544
H6 C4 3.4773 no . 4_544
H6 C5 3.0949 no . 4_544
H6 C8 3.0919 no . 4_544
H6 C9 3.5055 no . 1_554
H6 C9 2.9981 no . 4_544
H7 C2 3.3137 no . 4_544
H7 C3 3.2362 no . 4_544
H7 C4 3.2794 no . 4_544
H7 C5 3.3863 no . 4_544
H7 C6 3.4014 no . 4_544
H7 C7 3.3716 no . 4_544
H7 H4 3.1917 no . 1_554
H10 N1 2.5011 no . 1_554
H10 N1 3.4312 no . 4_554
H10 C9 3.3582 no . 4_554
H10 H12 2.8835 no . 4_544
H12 N1 3.5415 no . 4_544
H12 C10 3.0396 no . 4_545
H12 C11 2.8684 no . 4_545
H12 C12 3.2589 no . 4_545
H12 C16 3.2652 no . 4_545
H12 H10 2.8835 no . 4_545
H12 H12 3.5190 no . 4_544
H12 H12 3.5190 no . 4_545
H12 H16 3.5214 no . 4_545
H12 H16 3.5762 no . 4_555
H13 C11 3.4126 no . 4_545
H13 C12 3.2833 no . 4_545
H13 C13 3.0493 no . 4_545
H13 C14 3.4458 no . 3_657
H13 C14 2.9342 no . 4_545
H13 C15 3.5043 no . 2_646
H13 C15 3.0405 no . 4_545
H13 C16 3.2642 no . 4_545
H13 H13 3.5085 no . 4_544
H13 H13 3.5085 no . 4_545
H13 H14 3.3231 no . 2_646
H13 H14 2.6793 no . 3_657
H13 H14 3.3511 no . 4_545
H13 H15 2.7108 no . 2_646
H13 H15 3.5025 no . 4_545
H13 H15 3.5969 no . 4_555
H14 C13 3.5838 no . 2_656
H14 C13 3.1725 no . 3_657
H14 C14 3.2750 no . 3_657
H14 C15 3.2743 no . 2_646
H14 C15 3.2715 no . 3_656
H14 H13 3.3231 no . 2_656
H14 H13 2.6793 no . 3_657
H14 H13 3.3511 no . 4_544
H14 H14 3.5285 no . 2_646
H14 H14 3.5285 no . 2_656
H14 H14 2.8750 no . 3_657
H14 H15 2.7468 no . 2_646
H14 H15 2.7360 no . 3_656
H14 H15 2.8899 no . 4_555
H15 C13 3.2958 no . 2_656
H15 C13 3.3156 no . 4_554
H15 C14 3.3085 no . 2_656
H15 C14 3.0986 no . 3_656
H15 C14 2.8833 no . 4_554
H15 C15 3.3607 no . 3_656
H15 C15 3.2795 no . 4_554
H15 H13 2.7108 no . 2_656
H15 H13 3.5025 no . 4_544
H15 H13 3.5969 no . 4_554
H15 H14 2.7468 no . 2_656
H15 H14 2.7360 no . 3_656
H15 H14 2.8899 no . 4_554
H15 H15 3.2074 no . 3_656
H15 H15 3.5332 no . 4_554
H15 H15 3.5332 no . 4_555
H16 C9 3.5499 no . 4_554
H16 C11 2.9491 no . 4_554
H16 C12 3.0974 no . 4_554
H16 C13 3.3230 no . 4_554
H16 C14 3.4050 no . 4_554
H16 C15 3.2796 no . 4_554
H16 C16 3.0637 no . 4_554
H16 H12 3.5214 no . 4_544
H16 H12 3.5762 no . 4_554
H16 H16 3.5337 no . 4_554
H16 H16 3.5337 no . 4_555

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



####################################################################### 
# 
# 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_Compound_2d
_database_code_depnum_ccdc_archive 'CCDC 2034950'
loop_
_audit_author_name
_audit_author_address
'Masashi Mamada'
;Kyushu University
Japan
;
_audit_update_record             
;
2020-10-01 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;
_audit_creation_date             2019-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C18 H12 N)'
_chemical_formula_sum            'C36 H24 N2'
_chemical_formula_weight         484.57
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     100K
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.6708(4)
_cell_length_b                   7.2930(3)
_cell_length_c                   26.0182(11)
_cell_angle_alpha                93.342(4)
_cell_angle_beta                 91.641(4)
_cell_angle_gamma                91.948(4)
_cell_volume                     1262.31(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7504
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.6100
_cell_measurement_theta_min      2.2940
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            20689
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.353
_diffrn_ambient_temperature      100
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00   6.00   0.50    3.00    --    5.00  45.00 150.00  122
  2  ω     46.00  76.00   0.50    3.00    --    5.00  45.00 150.00   60
  3  ω     47.00  78.00   0.50    3.00    --  -10.30  45.00   0.00   62
  4  ω     42.00  76.00   0.50    3.00    --  -10.30  45.00  60.00   68
  5  ω    -99.00  41.00   0.50    3.00    --  -10.30  45.00  60.00  280
  6  ω    -34.00  41.00   0.50    3.00    --  -10.30  45.00   0.00  150
  7  ω    -92.00  79.00   0.50    3.00    --  -10.30  45.00 120.00  342
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC HyPix-6000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0179556000
_diffrn_orient_matrix_UB_12      0.0151162000
_diffrn_orient_matrix_UB_13      -0.0261828000
_diffrn_orient_matrix_UB_21      -0.0155247000
_diffrn_orient_matrix_UB_22      0.0951019000
_diffrn_orient_matrix_UB_23      0.0048465000
_diffrn_orient_matrix_UB_31      0.1037600000
_diffrn_orient_matrix_UB_32      0.0151879000
_diffrn_orient_matrix_UB_33      0.0061161000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR-E+
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4796
_reflns_number_total             5798
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5798
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+0.5982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1062
_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:
 C16(H16), C35(H35), C14(H14), C33(H33), C13(H13), C25(H25), C32(H32), C5(H5),
 C24(H24), C21(H21), C6(H6), C2(H2), C9(H9), C27(H27), C10(H10), C8(H8),
 C22(H22), C12(H12), C31(H31), C3(H3), C28(H28), C29(H29), C30(H30), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N19 N 0.02605(16) 0.63651(15) 0.41717(4) 0.0212(2) Uani 1 1 d . . . . .
N38 N 0.99406(16) 0.85527(15) 0.57161(4) 0.0223(2) Uani 1 1 d . . . . .
C17 C 0.33539(17) 0.53881(15) 0.47022(5) 0.0141(2) Uani 1 1 d . . . . .
C15 C 0.49486(17) 0.45147(15) 0.44543(5) 0.0141(2) Uani 1 1 d . . . . .
C36 C 0.67244(17) 0.95261(15) 0.52438(5) 0.0142(2) Uani 1 1 d . . . . .
C34 C 0.47204(18) 0.95753(15) 0.44567(5) 0.0145(2) Uani 1 1 d . . . . .
C16 C 0.34082(17) 0.58613(15) 0.52278(5) 0.0142(2) Uani 1 1 d . . . . .
H16 H 0.229827 0.645656 0.537519 0.017 Uiso 1 1 calc R . . . .
C35 C 0.64698(17) 0.91070(15) 0.47188(5) 0.0144(2) Uani 1 1 d . . . . .
H35 H 0.749142 0.849751 0.453613 0.017 Uiso 1 1 calc R . . . .
C14 C 0.48644(18) 0.39961(16) 0.39024(5) 0.0154(2) Uani 1 1 d . . . . .
H14 H 0.361288 0.403109 0.372027 0.018 Uiso 1 1 calc R . . . .
C33 C 0.43056(18) 0.91104(16) 0.39114(5) 0.0158(2) Uani 1 1 d . . . . .
H33 H 0.302821 0.942142 0.377848 0.019 Uiso 1 1 calc R . . . .
C1 C 0.71309(19) 0.16595(17) 0.20642(5) 0.0178(3) Uani 1 1 d . . . . .
C18 C 0.16281(18) 0.59041(16) 0.44027(5) 0.0156(2) Uani 1 1 d . . . . .
C37 C 0.85307(18) 0.89849(16) 0.54997(5) 0.0163(2) Uani 1 1 d . . . . .
C13 C 0.64671(19) 0.34761(16) 0.36433(5) 0.0170(2) Uani 1 1 d . . . . .
H13 H 0.769440 0.350824 0.383864 0.020 Uiso 1 1 calc R . . . .
C4 C 0.65957(19) 0.28655(16) 0.31022(5) 0.0171(2) Uani 1 1 d . . . . .
C25 C 0.58235(19) 0.68114(17) 0.21761(5) 0.0192(3) Uani 1 1 d . . . . .
H25 H 0.684050 0.658855 0.193430 0.023 Uiso 1 1 calc R . . . .
C23 C 0.49204(19) 0.77160(16) 0.30469(5) 0.0175(3) Uani 1 1 d . . . . .
C32 C 0.55233(19) 0.82956(16) 0.35782(5) 0.0175(3) Uani 1 1 d . . . . .
H32 H 0.685569 0.807949 0.369216 0.021 Uiso 1 1 calc R . . . .
C26 C 0.32276(19) 0.59877(17) 0.14759(5) 0.0181(3) Uani 1 1 d . . . . .
C20 C 0.38054(19) 0.65856(17) 0.20163(5) 0.0176(3) Uani 1 1 d . . . . .
C7 C 0.74036(19) 0.10232(17) 0.15188(5) 0.0181(3) Uani 1 1 d . . . . .
C5 C 0.49516(19) 0.25085(17) 0.27602(5) 0.0187(3) Uani 1 1 d . . . . .
H5 H 0.363235 0.267095 0.287908 0.022 Uiso 1 1 calc R . . . .
C24 C 0.63606(19) 0.73553(17) 0.26818(5) 0.0189(3) Uani 1 1 d . . . . .
H24 H 0.774185 0.748453 0.278137 0.023 Uiso 1 1 calc R . . . .
C21 C 0.23630(19) 0.69051(18) 0.23836(5) 0.0215(3) Uani 1 1 d . . . . .
H21 H 0.098246 0.674319 0.228570 0.026 Uiso 1 1 calc R . . . .
C6 C 0.52147(19) 0.19259(17) 0.22546(5) 0.0187(3) Uani 1 1 d . . . . .
H6 H 0.407270 0.170014 0.203044 0.022 Uiso 1 1 calc R . . . .
C2 C 0.8767(2) 0.20013(19) 0.24051(5) 0.0223(3) Uani 1 1 d . . . . .
H2 H 1.008523 0.183150 0.228635 0.027 Uiso 1 1 calc R . . . .
C9 C 0.6362(2) 0.09266(18) 0.06182(5) 0.0232(3) Uani 1 1 d . . . . .
H9 H 0.545424 0.127493 0.035624 0.028 Uiso 1 1 calc R . . . .
C27 C 0.4376(2) 0.65464(17) 0.10709(5) 0.0207(3) Uani 1 1 d . . . . .
H27 H 0.552944 0.733027 0.114142 0.025 Uiso 1 1 calc R . . . .
C10 C 0.7943(2) -0.01818(19) 0.04911(5) 0.0241(3) Uani 1 1 d . . . . .
H10 H 0.812682 -0.058754 0.014259 0.029 Uiso 1 1 calc R . . . .
C8 C 0.6102(2) 0.15275(17) 0.11261(5) 0.0209(3) Uani 1 1 d . . . . .
H8 H 0.502029 0.229535 0.120840 0.025 Uiso 1 1 calc R . . . .
C22 C 0.28966(19) 0.74534(18) 0.28882(5) 0.0211(3) Uani 1 1 d . . . . .
H22 H 0.187856 0.765533 0.313097 0.025 Uiso 1 1 calc R . . . .
C12 C 0.8990(2) -0.00971(18) 0.13838(5) 0.0218(3) Uani 1 1 d . . . . .
H12 H 0.989920 -0.045400 0.164413 0.026 Uiso 1 1 calc R . . . .
C31 C 0.1526(2) 0.48495(18) 0.13579(5) 0.0225(3) Uani 1 1 d . . . . .
H31 H 0.071261 0.446423 0.162824 0.027 Uiso 1 1 calc R . . . .
C3 C 0.85053(19) 0.25835(19) 0.29132(5) 0.0223(3) Uani 1 1 d . . . . .
H3 H 0.964726 0.279569 0.313809 0.027 Uiso 1 1 calc R . . . .
C28 C 0.3855(2) 0.59724(18) 0.05659(5) 0.0233(3) Uani 1 1 d . . . . .
H28 H 0.465628 0.636344 0.029398 0.028 Uiso 1 1 calc R . . . .
C29 C 0.2176(2) 0.48332(19) 0.04548(5) 0.0246(3) Uani 1 1 d . . . . .
H29 H 0.182881 0.443839 0.010828 0.029 Uiso 1 1 calc R . . . .
C30 C 0.1008(2) 0.42742(19) 0.08520(5) 0.0253(3) Uani 1 1 d . . . . .
H30 H -0.014910 0.349693 0.077845 0.030 Uiso 1 1 calc R . . . .
C11 C 0.9252(2) -0.06939(18) 0.08752(5) 0.0242(3) Uani 1 1 d . . . . .
H11 H 1.033468 -0.145702 0.078991 0.029 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
N19 C18 1.1487(16) . ?
N38 C37 1.1453(16) . ?
C17 C15 1.4110(16) . ?
C17 C16 1.3899(17) . ?
C17 C18 1.4445(16) . ?
C15 C16 1.3985(16) 2_666 ?
C15 C14 1.4623(16) . ?
C36 C34 1.4114(17) 2_676 ?
C36 C35 1.3865(17) . ?
C36 C37 1.4380(16) . ?
C34 C35 1.3972(17) . ?
C34 C33 1.4560(17) . ?
C14 C13 1.3343(17) . ?
C33 C32 1.3332(17) . ?
C1 C7 1.4852(17) . ?
C1 C6 1.3997(18) . ?
C1 C2 1.3928(18) . ?
C13 C4 1.4575(17) . ?
C4 C5 1.4000(17) . ?
C4 C3 1.3961(18) . ?
C25 C20 1.3990(17) . ?
C25 C24 1.3855(18) . ?
C23 C32 1.4629(17) . ?
C23 C24 1.3910(18) . ?
C23 C22 1.4040(18) . ?
C26 C20 1.4837(17) . ?
C26 C27 1.3921(18) . ?
C26 C31 1.3993(18) . ?
C20 C21 1.3912(18) . ?
C7 C8 1.3957(18) . ?
C7 C12 1.3989(18) . ?
C5 C6 1.3766(18) . ?
C21 C22 1.3830(18) . ?
C2 C3 1.3825(18) . ?
C9 C10 1.386(2) . ?
C9 C8 1.3854(18) . ?
C27 C28 1.3864(18) . ?
C10 C11 1.384(2) . ?
C12 C11 1.3866(19) . ?
C31 C30 1.3887(19) . ?
C28 C29 1.3852(19) . ?
C29 C30 1.384(2) . ?

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 C17 C18 119.79(11) . . ?
C16 C17 C15 122.45(11) . . ?
C16 C17 C18 117.69(11) . . ?
C17 C15 C14 122.05(11) . . ?
C16 C15 C17 115.72(11) 2_666 . ?
C16 C15 C14 122.21(11) 2_666 . ?
C34 C36 C37 118.13(11) 2_676 . ?
C35 C36 C34 123.32(11) . 2_676 ?
C35 C36 C37 118.53(11) . . ?
C36 C34 C33 120.06(11) 2_676 . ?
C35 C34 C36 116.26(11) . 2_676 ?
C35 C34 C33 123.62(11) . . ?
C17 C16 C15 121.83(11) . 2_666 ?
C36 C35 C34 120.43(11) . . ?
C13 C14 C15 122.93(11) . . ?
C32 C33 C34 127.07(11) . . ?
C6 C1 C7 121.05(11) . . ?
C2 C1 C7 121.33(11) . . ?
C2 C1 C6 117.62(11) . . ?
N19 C18 C17 177.98(13) . . ?
N38 C37 C36 178.07(13) . . ?
C14 C13 C4 128.97(12) . . ?
C5 C4 C13 125.07(11) . . ?
C3 C4 C13 117.39(11) . . ?
C3 C4 C5 117.53(11) . . ?
C24 C25 C20 120.97(12) . . ?
C24 C23 C32 120.43(11) . . ?
C24 C23 C22 117.52(11) . . ?
C22 C23 C32 122.02(11) . . ?
C33 C32 C23 123.60(12) . . ?
C27 C26 C20 120.59(11) . . ?
C27 C26 C31 118.12(12) . . ?
C31 C26 C20 121.30(11) . . ?
C25 C20 C26 121.04(11) . . ?
C21 C20 C25 117.71(11) . . ?
C21 C20 C26 121.23(11) . . ?
C8 C7 C1 121.34(11) . . ?
C8 C7 C12 117.99(12) . . ?
C12 C7 C1 120.66(11) . . ?
C6 C5 C4 121.10(12) . . ?
C25 C24 C23 121.40(12) . . ?
C22 C21 C20 121.38(12) . . ?
C5 C6 C1 121.33(11) . . ?
C3 C2 C1 121.13(12) . . ?
C8 C9 C10 120.17(13) . . ?
C28 C27 C26 120.77(12) . . ?
C11 C10 C9 119.61(12) . . ?
C9 C8 C7 121.07(12) . . ?
C21 C22 C23 120.98(12) . . ?
C11 C12 C7 120.90(13) . . ?
C30 C31 C26 121.04(12) . . ?
C2 C3 C4 121.28(12) . . ?
C29 C28 C27 120.53(13) . . ?
C30 C29 C28 119.54(12) . . ?
C29 C30 C31 120.00(13) . . ?
C10 C11 C12 120.25(13) . . ?

_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 1.171
_oxdiff_exptl_absorpt_empirical_full_min 0.831
####################################################################### 
# 
# 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_Compound_3c
_database_code_depnum_ccdc_archive 'CCDC 2034953'
loop_
_audit_author_name
_audit_author_address
'Masashi Mamada'
;Kyushu University
Japan
;
_audit_update_record             
;
2020-10-01 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H22 N2'
_chemical_formula_sum            'C32 H22 N2'
_chemical_formula_weight         434.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   14.024(4)
_cell_length_b                   6.820(2)
_cell_length_c                   23.678(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.483(10)
_cell_angle_gamma                90
_cell_volume                     2260.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2399
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      27.63

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.222
_diffrn_reflns_number            17932
_diffrn_reflns_av_unetI/netI     0.1064
_diffrn_reflns_av_R_equivalents  0.0920
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.043
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.939
_reflns_number_total             7473
_reflns_number_gt                5435
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_max     0.871
_reflns_Friedel_fraction_full    0.871
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0661P)²+2.4594P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1339 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.5(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7473
_refine_ls_number_parameters     613
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.0998
_refine_ls_wR_factor_ref         0.2182
_refine_ls_wR_factor_gt          0.1940
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8937(4) 0.7053(11) 0.6299(2) 0.0409(14) Uani 1 1 d . . . . .
N2 N 0.4041(5) 0.6853(11) 0.1231(3) 0.0483(17) Uani 1 1 d . . . . .
N3 N 1.1852(6) 1.6645(11) 0.8575(3) 0.059(2) Uani 1 1 d . . . . .
N4 N 0.6888(4) 0.7257(12) 0.3501(2) 0.0476(16) Uani 1 1 d . . . . .
C1 C 0.4865(6) 0.7237(14) 0.4428(3) 0.052(2) Uani 1 1 d . . . . .
H1 H 0.5299 0.7203 0.4135 0.063 Uiso 1 1 calc R U . . .
C2 C 0.5286(6) 0.7258(13) 0.5024(3) 0.0429(18) Uani 1 1 d . . . . .
C3 C 0.4754(5) 0.7254(12) 0.5500(3) 0.0447(18) Uani 1 1 d . . . . .
H3 H 0.4076 0.7236 0.5456 0.054 Uiso 1 1 calc R U . . .
C4 C 0.5205(5) 0.7275(12) 0.6046(3) 0.0354(15) Uani 1 1 d . . . . .
H4 H 0.4827 0.7265 0.6365 0.043 Uiso 1 1 calc R U . . .
C5 C 0.6191(5) 0.7310(12) 0.6128(3) 0.0342(15) Uani 1 1 d . . . . .
C6 C 0.6705(5) 0.7337(13) 0.5644(3) 0.0423(18) Uani 1 1 d . . . . .
H6 H 0.7383 0.7372 0.5682 0.051 Uiso 1 1 calc R U . . .
C7 C 0.6257(5) 0.7316(14) 0.5114(3) 0.048(2) Uani 1 1 d . . . . .
H7 H 0.6638 0.7342 0.4796 0.057 Uiso 1 1 calc R U . . .
C8 C 0.6584(5) 0.7298(12) 0.6712(3) 0.0350(16) Uani 1 1 d . . . . .
H8 H 0.6117 0.7342 0.6986 0.042 Uiso 1 1 calc R U . . .
C9 C 0.7494(4) 0.7237(11) 0.6933(2) 0.0286(14) Uani 1 1 d . . . . .
C10 C 0.8282(5) 0.7146(12) 0.6569(3) 0.0318(14) Uani 1 1 d . . . . .
C11 C 0.7773(5) 0.7246(11) 0.7550(2) 0.0310(14) Uani 1 1 d . . . . .
C12 C 0.7089(5) 0.7178(12) 0.7950(2) 0.0339(15) Uani 1 1 d . . . . .
H12 H 0.6430 0.7124 0.7831 0.041 Uiso 1 1 calc R U . . .
C13 C 0.7367(5) 0.7187(13) 0.8524(3) 0.0440(18) Uani 1 1 d . . . . .
H13 H 0.6894 0.7177 0.8795 0.053 Uiso 1 1 calc R U . . .
C14 C 0.8311(6) 0.7210(13) 0.8703(3) 0.0470(19) Uani 1 1 d . . . . .
H14 H 0.8491 0.7175 0.9096 0.056 Uiso 1 1 calc R U . . .
C15 C 0.9001(6) 0.7284(13) 0.8315(3) 0.050(2) Uani 1 1 d . . . . .
H15 H 0.9658 0.7320 0.8439 0.060 Uiso 1 1 calc R U . . .
C16 C 0.8733(5) 0.7307(12) 0.7744(3) 0.0408(17) Uani 1 1 d . . . . .
H16 H 0.9212 0.7366 0.7478 0.049 Uiso 1 1 calc R U . . .
C17 C 0.3977(6) 0.7260(14) 0.4279(3) 0.051(2) Uani 1 1 d . . . . .
H17 H 0.3546 0.7291 0.4573 0.061 Uiso 1 1 calc R U . . .
C18 C 0.3549(6) 0.7244(12) 0.3687(3) 0.0410(18) Uani 1 1 d . . . . .
C19 C 0.2569(5) 0.7256(12) 0.3610(3) 0.0388(16) Uani 1 1 d . . . . .
H19 H 0.2195 0.7272 0.3931 0.047 Uiso 1 1 calc R U . . .
C20 C 0.2126(5) 0.7245(11) 0.3082(3) 0.0359(15) Uani 1 1 d . . . . .
H20 H 0.1448 0.7248 0.3046 0.043 Uiso 1 1 calc R U . . .
C21 C 0.2629(4) 0.7230(12) 0.2590(2) 0.0312(14) Uani 1 1 d . . . . .
C22 C 0.3623(5) 0.7250(13) 0.2656(3) 0.0378(16) Uani 1 1 d . . . . .
H22 H 0.3995 0.7261 0.2334 0.045 Uiso 1 1 calc R U . . .
C23 C 0.4071(5) 0.7254(13) 0.3203(3) 0.0457(18) Uani 1 1 d . . . . .
H23 H 0.4749 0.7265 0.3245 0.055 Uiso 1 1 calc R U . . .
C24 C 0.2064(4) 0.7274(11) 0.2051(2) 0.0300(14) Uani 1 1 d . . . . .
H24 H 0.1396 0.7386 0.2090 0.036 Uiso 1 1 calc R U . . .
C25 C 0.2299(5) 0.7187(12) 0.1516(2) 0.0312(14) Uani 1 1 d . . . . .
C26 C 0.3273(5) 0.7006(12) 0.1370(2) 0.0326(15) Uani 1 1 d . . . . .
C27 C 0.1579(5) 0.7349(11) 0.1016(3) 0.0322(15) Uani 1 1 d . . . . .
C28 C 0.0612(5) 0.7200(14) 0.1071(3) 0.0416(17) Uani 1 1 d . . . . .
H28 H 0.0381 0.6933 0.1432 0.050 Uiso 1 1 calc R U . . .
C29 C -0.0029(5) 0.7433(14) 0.0611(3) 0.049(2) Uani 1 1 d . . . . .
H29 H -0.0695 0.7309 0.0657 0.059 Uiso 1 1 calc R U . . .
C30 C 0.0288(6) 0.7845(12) 0.0083(3) 0.050(2) Uani 1 1 d . . . . .
H30 H -0.0154 0.8019 -0.0233 0.060 Uiso 1 1 calc R U . . .
C31 C 0.1246(6) 0.7998(12) 0.0023(3) 0.053(2) Uani 1 1 d . . . . .
H31 H 0.1475 0.8284 -0.0337 0.064 Uiso 1 1 calc R U . . .
C32 C 0.1882(5) 0.7738(11) 0.0485(3) 0.042(2) Uani 1 1 d . . . . .
H32 H 0.2548 0.7830 0.0435 0.050 Uiso 1 1 calc R U . . .
C33 C 0.9894(6) 1.247(3) 0.6085(4) 0.116(6) Uani 1 1 d D . . . .
H33 H 0.9769 1.3809 0.6002 0.139 Uiso 1 1 calc R U . . .
C34 C 1.0437(5) 1.217(2) 0.6633(3) 0.067(3) Uani 1 1 d . . . . .
C35 C 1.0720(6) 1.0314(19) 0.6862(4) 0.064(3) Uani 1 1 d . . . . .
H35 H 1.0581 0.9151 0.6652 0.077 Uiso 1 1 calc R U . . .
C36 C 1.1211(6) 1.0200(14) 0.7402(3) 0.047(2) Uani 1 1 d . . . . .
H36 H 1.1389 0.8958 0.7556 0.057 Uiso 1 1 calc R U . . .
C37 C 1.1433(5) 1.1905(13) 0.7709(3) 0.0377(19) Uani 1 1 d . . . . .
C38 C 1.1133(6) 1.3686(14) 0.7461(4) 0.057(2) Uani 1 1 d . . . . .
H38 H 1.1279 1.4868 0.7661 0.068 Uiso 1 1 calc R U . . .
C39 C 1.0647(7) 1.3800(18) 0.6954(4) 0.069(3) Uani 1 1 d . . . . .
H39 H 1.0443 1.5048 0.6815 0.083 Uiso 1 1 calc R U . . .
C40 C 1.1976(5) 1.1641(11) 0.8246(3) 0.0374(19) Uani 1 1 d . . . . .
H40 H 1.2142 1.0315 0.8328 0.045 Uiso 1 1 calc R U . . .
C41 C 1.2290(5) 1.2914(10) 0.8648(3) 0.0316(16) Uani 1 1 d . . . . .
C42 C 1.2053(6) 1.4976(13) 0.8600(3) 0.044(2) Uani 1 1 d . . . . .
C43 C 1.2887(4) 1.2402(10) 0.9162(3) 0.0294(15) Uani 1 1 d . . . . .
C44 C 1.3241(5) 1.0509(11) 0.9249(3) 0.0399(19) Uani 1 1 d . . . . .
H44 H 1.3086 0.9537 0.8971 0.048 Uiso 1 1 calc R U . . .
C45 C 1.3810(6) 0.9989(13) 0.9723(3) 0.046(2) Uani 1 1 d . . . . .
H45 H 1.4040 0.8686 0.9768 0.056 Uiso 1 1 calc R U . . .
C46 C 1.4037(6) 1.1388(13) 1.0128(3) 0.048(2) Uani 1 1 d . . . . .
H46 H 1.4419 1.1048 1.0458 0.057 Uiso 1 1 calc R U . . .
C47 C 1.3712(6) 1.3264(14) 1.0055(3) 0.055(3) Uani 1 1 d . . . . .
H47 H 1.3885 1.4230 1.0332 0.066 Uiso 1 1 calc R U . . .
C48 C 1.3127(6) 1.3780(13) 0.9579(3) 0.050(2) Uani 1 1 d . . . . .
H48 H 1.2892 1.5083 0.9541 0.060 Uiso 1 1 calc R U . . .
C49 C 0.9587(7) 1.141(2) 0.5734(4) 0.087(4) Uani 1 1 d D . . . .
H49 H 0.9721 1.0070 0.5810 0.105 Uiso 1 1 calc R U . . .
C50 C 0.9028(5) 1.1755(18) 0.5193(3) 0.059(3) Uani 1 1 d . . . . .
C51 C 0.8781(6) 1.0116(16) 0.4880(4) 0.062(3) Uani 1 1 d . . . . .
H51 H 0.8969 0.8860 0.5021 0.074 Uiso 1 1 calc R U . . .
C52 C 0.8274(6) 1.0252(14) 0.4375(3) 0.049(2) Uani 1 1 d . . . . .
H52 H 0.8136 0.9089 0.4164 0.059 Uiso 1 1 calc R U . . .
C53 C 0.7945(5) 1.2080(14) 0.4150(3) 0.0419(18) Uani 1 1 d . . . . .
C54 C 0.8171(6) 1.3744(14) 0.4471(3) 0.049(2) Uani 1 1 d . . . . .
H54 H 0.7962 1.4997 0.4340 0.058 Uiso 1 1 calc R U . . .
C55 C 0.8700(6) 1.3575(16) 0.4982(4) 0.059(3) Uani 1 1 d . . . . .
H55 H 0.8846 1.4726 0.5196 0.070 Uiso 1 1 calc R U . . .
C56 C 0.7398(5) 1.2320(12) 0.3612(2) 0.0340(16) Uani 1 1 d . . . . .
H56 H 0.7333 1.3644 0.3491 0.041 Uiso 1 1 calc R U . . .
C57 C 0.6961(5) 1.1000(10) 0.3250(3) 0.0331(17) Uani 1 1 d . . . . .
C58 C 0.6937(5) 0.8943(13) 0.3390(3) 0.0401(18) Uani 1 1 d . . . . .
C59 C 0.6425(5) 1.1492(11) 0.2711(3) 0.0343(19) Uani 1 1 d . . . . .
C60 C 0.6104(5) 1.0044(11) 0.2335(3) 0.0398(19) Uani 1 1 d . . . . .
H60 H 0.6220 0.8706 0.2427 0.048 Uiso 1 1 calc R U . . .
C61 C 0.5622(6) 1.0524(14) 0.1832(3) 0.050(2) Uani 1 1 d . . . . .
H61 H 0.5425 0.9514 0.1575 0.060 Uiso 1 1 calc R U . . .
C62 C 0.5418(5) 1.2468(15) 0.1695(3) 0.047(2) Uani 1 1 d . . . . .
H62 H 0.5074 1.2789 0.1350 0.056 Uiso 1 1 calc R U . . .
C63 C 0.5721(6) 1.3913(14) 0.2066(3) 0.050(2) Uani 1 1 d . . . . .
H63 H 0.5585 1.5245 0.1976 0.060 Uiso 1 1 calc R U . . .
C64 C 0.6221(6) 1.3459(12) 0.2568(3) 0.045(2) Uani 1 1 d . . . . .
H64 H 0.6430 1.4479 0.2819 0.054 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C10 1.152(8) . ?
N2 C26 1.151(8) . ?
N3 C42 1.174(10) . ?
N4 C58 1.182(11) . ?
C1 C17 1.274(10) . ?
C1 C2 1.495(9) . ?
C1 H1 0.9500 . ?
C2 C7 1.366(10) . ?
C2 C3 1.390(10) . ?
C3 C4 1.404(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(9) . ?
C5 C8 1.458(8) . ?
C6 C7 1.369(9) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.350(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.444(9) . ?
C9 C11 1.489(8) . ?
C11 C12 1.389(9) . ?
C11 C16 1.397(9) . ?
C12 C13 1.391(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.365(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.375(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(9) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.490(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.375(10) . ?
C18 C23 1.396(10) . ?
C19 C20 1.364(9) . ?
C19 H19 0.9500 . ?
C20 C21 1.398(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.393(9) . ?
C21 C24 1.461(8) . ?
C22 C23 1.405(9) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.329(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.433(9) . ?
C25 C27 1.513(8) . ?
C27 C28 1.375(9) . ?
C27 C32 1.377(9) . ?
C28 C29 1.380(9) . ?
C28 H28 0.9500 . ?
C29 C30 1.380(11) . ?
C29 H29 0.9500 . ?
C30 C31 1.363(11) . ?
C30 H30 0.9500 . ?
C31 C32 1.381(10) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C49 1.161(13) . ?
C33 C34 1.477(12) . ?
C33 H33 0.9500 . ?
C34 C39 1.371(16) . ?
C34 C35 1.422(16) . ?
C35 C36 1.417(11) . ?
C35 H35 0.9500 . ?
C36 C37 1.397(11) . ?
C36 H36 0.9500 . ?
C37 C38 1.403(12) . ?
C37 C40 1.452(9) . ?
C38 C39 1.346(11) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 C41 1.343(9) . ?
C40 H40 0.9500 . ?
C41 C42 1.448(11) . ?
C41 C43 1.475(9) . ?
C43 C48 1.391(9) . ?
C43 C44 1.394(10) . ?
C44 C45 1.382(10) . ?
C44 H44 0.9500 . ?
C45 C46 1.377(11) . ?
C45 H45 0.9500 . ?
C46 C47 1.365(12) . ?
C46 H46 0.9500 . ?
C47 C48 1.397(11) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
C49 C50 1.479(12) . ?
C49 H49 0.9500 . ?
C50 C51 1.374(14) . ?
C50 C55 1.406(14) . ?
C51 C52 1.358(11) . ?
C51 H51 0.9500 . ?
C52 C53 1.421(12) . ?
C52 H52 0.9500 . ?
C53 C54 1.391(11) . ?
C53 C56 1.455(8) . ?
C54 C55 1.384(11) . ?
C54 H54 0.9500 . ?
C55 H55 0.9500 . ?
C56 C57 1.363(9) . ?
C56 H56 0.9500 . ?
C57 C58 1.442(11) . ?
C57 C59 1.480(10) . ?
C59 C60 1.385(9) . ?
C59 C64 1.409(10) . ?
C60 C61 1.373(10) . ?
C60 H60 0.9500 . ?
C61 C62 1.391(13) . ?
C61 H61 0.9500 . ?
C62 C63 1.370(12) . ?
C62 H62 0.9500 . ?
C63 C64 1.377(10) . ?
C63 H63 0.9500 . ?
C64 H64 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
C17 C1 C2 125.8(8) . . ?
C17 C1 H1 117.1 . . ?
C2 C1 H1 117.1 . . ?
C7 C2 C3 116.8(6) . . ?
C7 C2 C1 118.8(7) . . ?
C3 C2 C1 124.4(7) . . ?
C2 C3 C4 120.8(7) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 121.4(6) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 116.6(6) . . ?
C4 C5 C8 116.8(6) . . ?
C6 C5 C8 126.6(6) . . ?
C7 C6 C5 121.6(7) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C2 C7 C6 122.8(7) . . ?
C2 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C9 C8 C5 131.5(6) . . ?
C9 C8 H8 114.2 . . ?
C5 C8 H8 114.2 . . ?
C8 C9 C10 120.6(5) . . ?
C8 C9 C11 124.5(6) . . ?
C10 C9 C11 114.9(5) . . ?
N1 C10 C9 177.0(6) . . ?
C12 C11 C16 117.9(6) . . ?
C12 C11 C9 121.1(5) . . ?
C16 C11 C9 120.9(6) . . ?
C11 C12 C13 120.1(6) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.8(7) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.1(6) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 119.6(7) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C11 121.4(7) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C1 C17 C18 126.3(8) . . ?
C1 C17 H17 116.8 . . ?
C18 C17 H17 116.8 . . ?
C19 C18 C23 117.4(6) . . ?
C19 C18 C17 117.8(7) . . ?
C23 C18 C17 124.8(7) . . ?
C20 C19 C18 121.1(7) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 122.7(7) . . ?
C19 C20 H20 118.6 . . ?
C21 C20 H20 118.6 . . ?
C22 C21 C20 117.2(5) . . ?
C22 C21 C24 125.8(6) . . ?
C20 C21 C24 117.0(6) . . ?
C21 C22 C23 119.5(6) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C18 C23 C22 122.0(7) . . ?
C18 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
C25 C24 C21 132.7(6) . . ?
C25 C24 H24 113.6 . . ?
C21 C24 H24 113.6 . . ?
C24 C25 C26 121.9(6) . . ?
C24 C25 C27 123.3(6) . . ?
C26 C25 C27 114.7(5) . . ?
N2 C26 C25 177.2(7) . . ?
C28 C27 C32 117.6(6) . . ?
C28 C27 C25 122.4(6) . . ?
C32 C27 C25 120.0(6) . . ?
C27 C28 C29 121.1(7) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C28 C29 C30 120.5(7) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C31 C30 C29 119.0(7) . . ?
C31 C30 H30 120.5 . . ?
C29 C30 H30 120.5 . . ?
C30 C31 C32 120.1(8) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C27 C32 C31 121.8(7) . . ?
C27 C32 H32 119.1 . . ?
C31 C32 H32 119.1 . . ?
C49 C33 C34 133.7(17) . . ?
C49 C33 H33 113.1 . . ?
C34 C33 H33 113.1 . . ?
C39 C34 C35 117.7(7) . . ?
C39 C34 C33 117.2(13) . . ?
C35 C34 C33 125.1(13) . . ?
C36 C35 C34 120.1(9) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C37 C36 C35 120.4(9) . . ?
C37 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C36 C37 C38 116.8(6) . . ?
C36 C37 C40 116.2(7) . . ?
C38 C37 C40 127.0(7) . . ?
C39 C38 C37 123.1(9) . . ?
C39 C38 H38 118.4 . . ?
C37 C38 H38 118.4 . . ?
C38 C39 C34 121.9(10) . . ?
C38 C39 H39 119.1 . . ?
C34 C39 H39 119.1 . . ?
C41 C40 C37 132.2(7) . . ?
C41 C40 H40 113.9 . . ?
C37 C40 H40 113.9 . . ?
C40 C41 C42 120.6(6) . . ?
C40 C41 C43 125.2(6) . . ?
C42 C41 C43 114.2(6) . . ?
N3 C42 C41 178.3(9) . . ?
C48 C43 C44 116.8(6) . . ?
C48 C43 C41 121.8(7) . . ?
C44 C43 C41 121.4(6) . . ?
C45 C44 C43 122.7(7) . . ?
C45 C44 H44 118.6 . . ?
C43 C44 H44 118.6 . . ?
C46 C45 C44 119.1(8) . . ?
C46 C45 H45 120.5 . . ?
C44 C45 H45 120.5 . . ?
C47 C46 C45 120.0(8) . . ?
C47 C46 H46 120.0 . . ?
C45 C46 H46 120.0 . . ?
C46 C47 C48 120.9(8) . . ?
C46 C47 H47 119.6 . . ?
C48 C47 H47 119.6 . . ?
C43 C48 C47 120.5(8) . . ?
C43 C48 H48 119.7 . . ?
C47 C48 H48 119.7 . . ?
C33 C49 C50 132.5(14) . . ?
C33 C49 H49 113.7 . . ?
C50 C49 H49 113.7 . . ?
C51 C50 C55 117.4(7) . . ?
C51 C50 C49 116.2(10) . . ?
C55 C50 C49 126.3(10) . . ?
C52 C51 C50 121.4(10) . . ?
C52 C51 H51 119.3 . . ?
C50 C51 H51 119.3 . . ?
C51 C52 C53 122.0(9) . . ?
C51 C52 H52 119.0 . . ?
C53 C52 H52 119.0 . . ?
C54 C53 C52 117.0(6) . . ?
C54 C53 C56 118.4(8) . . ?
C52 C53 C56 124.6(8) . . ?
C55 C54 C53 120.1(9) . . ?
C55 C54 H54 120.0 . . ?
C53 C54 H54 120.0 . . ?
C54 C55 C50 122.1(9) . . ?
C54 C55 H55 119.0 . . ?
C50 C55 H55 119.0 . . ?
C57 C56 C53 132.0(8) . . ?
C57 C56 H56 114.0 . . ?
C53 C56 H56 114.0 . . ?
C56 C57 C58 120.9(7) . . ?
C56 C57 C59 125.3(6) . . ?
C58 C57 C59 113.7(6) . . ?
N4 C58 C57 178.0(8) . . ?
C60 C59 C64 118.1(7) . . ?
C60 C59 C57 121.3(7) . . ?
C64 C59 C57 120.6(6) . . ?
C61 C60 C59 120.7(8) . . ?
C61 C60 H60 119.7 . . ?
C59 C60 H60 119.7 . . ?
C60 C61 C62 120.9(8) . . ?
C60 C61 H61 119.6 . . ?
C62 C61 H61 119.6 . . ?
C63 C62 C61 119.0(7) . . ?
C63 C62 H62 120.5 . . ?
C61 C62 H62 120.5 . . ?
C62 C63 C64 120.8(9) . . ?
C62 C63 H63 119.6 . . ?
C64 C63 H63 119.6 . . ?
C63 C64 C59 120.4(7) . . ?
C63 C64 H64 119.8 . . ?
C59 C64 H64 119.8 . . ?

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
C17 C1 C2 C7 -177.2(9) . . . . ?
C17 C1 C2 C3 1.8(15) . . . . ?
C7 C2 C3 C4 -1.0(13) . . . . ?
C1 C2 C3 C4 -180.0(7) . . . . ?
C2 C3 C4 C5 0.3(13) . . . . ?
C3 C4 C5 C6 0.5(12) . . . . ?
C3 C4 C5 C8 -179.1(7) . . . . ?
C4 C5 C6 C7 -0.5(13) . . . . ?
C8 C5 C6 C7 179.0(8) . . . . ?
C3 C2 C7 C6 1.0(14) . . . . ?
C1 C2 C7 C6 -179.9(9) . . . . ?
C5 C6 C7 C2 -0.3(15) . . . . ?
C4 C5 C8 C9 176.6(8) . . . . ?
C6 C5 C8 C9 -2.8(15) . . . . ?
C5 C8 C9 C10 -0.7(13) . . . . ?
C5 C8 C9 C11 179.7(8) . . . . ?
C8 C9 C11 C12 4.7(12) . . . . ?
C10 C9 C11 C12 -175.0(7) . . . . ?
C8 C9 C11 C16 -175.8(8) . . . . ?
C10 C9 C11 C16 4.5(11) . . . . ?
C16 C11 C12 C13 0.5(12) . . . . ?
C9 C11 C12 C13 180.0(7) . . . . ?
C11 C12 C13 C14 -1.7(13) . . . . ?
C12 C13 C14 C15 2.0(14) . . . . ?
C13 C14 C15 C16 -0.9(14) . . . . ?
C14 C15 C16 C11 -0.4(13) . . . . ?
C12 C11 C16 C15 0.5(12) . . . . ?
C9 C11 C16 C15 -178.9(8) . . . . ?
C2 C1 C17 C18 179.9(8) . . . . ?
C1 C17 C18 C19 179.4(9) . . . . ?
C1 C17 C18 C23 -1.9(15) . . . . ?
C23 C18 C19 C20 1.1(13) . . . . ?
C17 C18 C19 C20 179.9(8) . . . . ?
C18 C19 C20 C21 -0.3(13) . . . . ?
C19 C20 C21 C22 -0.8(12) . . . . ?
C19 C20 C21 C24 -178.4(7) . . . . ?
C20 C21 C22 C23 1.0(12) . . . . ?
C24 C21 C22 C23 178.4(8) . . . . ?
C19 C18 C23 C22 -0.9(13) . . . . ?
C17 C18 C23 C22 -179.6(8) . . . . ?
C21 C22 C23 C18 -0.2(13) . . . . ?
C22 C21 C24 C25 6.1(14) . . . . ?
C20 C21 C24 C25 -176.5(8) . . . . ?
C21 C24 C25 C26 0.3(13) . . . . ?
C21 C24 C25 C27 -177.2(8) . . . . ?
C24 C25 C27 C28 -13.5(12) . . . . ?
C26 C25 C27 C28 168.8(8) . . . . ?
C24 C25 C27 C32 163.8(8) . . . . ?
C26 C25 C27 C32 -14.0(10) . . . . ?
C32 C27 C28 C29 0.0(12) . . . . ?
C25 C27 C28 C29 177.3(8) . . . . ?
C27 C28 C29 C30 -0.8(14) . . . . ?
C28 C29 C30 C31 0.7(13) . . . . ?
C29 C30 C31 C32 0.2(12) . . . . ?
C28 C27 C32 C31 0.8(11) . . . . ?
C25 C27 C32 C31 -176.6(7) . . . . ?
C30 C31 C32 C27 -0.9(12) . . . . ?
C49 C33 C34 C39 -177.1(11) . . . . ?
C49 C33 C34 C35 0.0(17) . . . . ?
C39 C34 C35 C36 -0.7(12) . . . . ?
C33 C34 C35 C36 -177.7(8) . . . . ?
C34 C35 C36 C37 -1.1(12) . . . . ?
C35 C36 C37 C38 1.2(11) . . . . ?
C35 C36 C37 C40 -177.1(7) . . . . ?
C36 C37 C38 C39 0.4(12) . . . . ?
C40 C37 C38 C39 178.5(8) . . . . ?
C37 C38 C39 C34 -2.3(15) . . . . ?
C35 C34 C39 C38 2.3(13) . . . . ?
C33 C34 C39 C38 179.6(8) . . . . ?
C36 C37 C40 C41 -178.3(8) . . . . ?
C38 C37 C40 C41 3.6(14) . . . . ?
C37 C40 C41 C42 3.3(13) . . . . ?
C37 C40 C41 C43 -176.5(7) . . . . ?
C40 C41 C43 C48 -175.3(7) . . . . ?
C42 C41 C43 C48 4.9(10) . . . . ?
C40 C41 C43 C44 5.1(11) . . . . ?
C42 C41 C43 C44 -174.7(7) . . . . ?
C48 C43 C44 C45 -0.3(11) . . . . ?
C41 C43 C44 C45 179.4(7) . . . . ?
C43 C44 C45 C46 0.1(12) . . . . ?
C44 C45 C46 C47 -0.8(13) . . . . ?
C45 C46 C47 C48 1.7(15) . . . . ?
C44 C43 C48 C47 1.1(11) . . . . ?
C41 C43 C48 C47 -178.5(7) . . . . ?
C46 C47 C48 C43 -1.8(14) . . . . ?
C34 C33 C49 C50 178.6(8) . . . . ?
C33 C49 C50 C51 -179.8(11) . . . . ?
C33 C49 C50 C55 -2.2(17) . . . . ?
C55 C50 C51 C52 2.7(13) . . . . ?
C49 C50 C51 C52 -179.5(8) . . . . ?
C50 C51 C52 C53 -2.1(14) . . . . ?
C51 C52 C53 C54 0.5(11) . . . . ?
C51 C52 C53 C56 -179.9(8) . . . . ?
C52 C53 C54 C55 0.5(11) . . . . ?
C56 C53 C54 C55 -179.2(7) . . . . ?
C53 C54 C55 C50 0.2(13) . . . . ?
C51 C50 C55 C54 -1.8(12) . . . . ?
C49 C50 C55 C54 -179.3(8) . . . . ?
C54 C53 C56 C57 -169.5(8) . . . . ?
C52 C53 C56 C57 10.9(12) . . . . ?
C53 C56 C57 C58 4.2(12) . . . . ?
C53 C56 C57 C59 180.0(7) . . . . ?
C56 C57 C59 C60 172.0(7) . . . . ?
C58 C57 C59 C60 -12.0(10) . . . . ?
C56 C57 C59 C64 -8.4(12) . . . . ?
C58 C57 C59 C64 167.6(7) . . . . ?
C64 C59 C60 C61 1.5(12) . . . . ?
C57 C59 C60 C61 -178.9(7) . . . . ?
C59 C60 C61 C62 -1.9(12) . . . . ?
C60 C61 C62 C63 1.2(12) . . . . ?
C61 C62 C63 C64 0.0(12) . . . . ?
C62 C63 C64 C59 -0.4(13) . . . . ?
C60 C59 C64 C63 -0.3(12) . . . . ?
C57 C59 C64 C63 -180.0(7) . . . . ?

_refine_diff_density_max         0.552
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_Compound_3a
_database_code_depnum_ccdc_archive 'CCDC 2034951'
loop_
_audit_author_name
_audit_author_address
'Masashi Mamada'
;Kyushu University
Japan
;
_audit_update_record             
;
2020-10-01 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;
_audit_creation_date             2020-09-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24'
_chemical_formula_sum            'C30 H24'
_chemical_formula_weight         384.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     100K
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   26.100(3)
_cell_length_b                   7.4249(8)
_cell_length_c                   15.9316(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.784(10)
_cell_angle_gamma                90
_cell_volume                     3010.8(6)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    2116
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.7820
_cell_measurement_theta_min      2.3690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1224
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 10 -3 0.0255
-2 -1 -22 0.0300
1 -10 2 0.0826
2 1 21 0.0045
-36 2 6 0.0076
-37 0 6 0.0060
37 0 -6 0.0060

_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.012
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.5455 10.3681 -2.6378 -0.0000 -0.0000 1.0000
-2.0610 -0.8319 -21.5236 -0.3416 -0.9385 0.0499
1.4723 -10.4103 1.8577 -0.0124 -0.0341 -0.9993
1.9863 1.3513 21.4186 0.3420 0.9397 0.0000
-36.3030 1.6257 5.6240 0.9214 -0.3354 0.1961
-36.7128 -0.4157 6.2629 0.9397 -0.3420 -0.0000
36.7128 0.4157 -6.2629 -0.9397 0.3420 0.0000

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_unetI/netI     0.0896
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22613
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.401
_diffrn_ambient_temperature      100
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     27.00  65.00   0.50  120.00    --  -10.50  45.00  60.00   76
  2  ω    -85.00 -11.00   0.50  120.00    --  -10.50  45.00 150.00  148
  3  ω     27.00  74.00   0.50  120.00    --  -10.50  45.00 150.00   94
  4  ω    -98.00   7.00   0.50  120.00    --  -10.50  45.00  60.00  210
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC HyPix-6000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0225419000
_diffrn_orient_matrix_UB_12      0.0012148000
_diffrn_orient_matrix_UB_13      0.0179822000
_diffrn_orient_matrix_UB_21      0.0162563000
_diffrn_orient_matrix_UB_22      0.0129930000
_diffrn_orient_matrix_UB_23      0.0415455000
_diffrn_orient_matrix_UB_31      -0.0020584000
_diffrn_orient_matrix_UB_32      0.0946722000
_diffrn_orient_matrix_UB_33      -0.0057820000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR-E+
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3425
_reflns_number_total             6907
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         6907
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1475
_refine_ls_R_factor_gt           0.0655
_refine_ls_restrained_S_all      0.980
_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)+(0.0920P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1870
_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:
 C1(H1), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22),
  C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30),
 C31(H31), C33(H33), C34(H34), C36(H36), C37(H37), C38(H38), C39(H39), C41(H41),
  C42(H42), C43(H43), C44(H44), C45(H45)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.39934(9) -0.0149(3) 0.31301(14) 0.0184(5) Uani 1 1 d . . . . .
H1 H 0.400456 -0.065590 0.258694 0.022 Uiso 1 1 calc R U . . .
C2 C 0.34757(9) 0.0029(3) 0.33286(13) 0.0154(5) Uani 1 1 d . . . . .
C3 C 0.33807(9) 0.0800(3) 0.40842(14) 0.0171(5) Uani 1 1 d . . . . .
H3 H 0.366401 0.130136 0.449699 0.021 Uiso 1 1 calc R U . . .
C4 C 0.28851(9) 0.0837(3) 0.42311(14) 0.0166(5) Uani 1 1 d . . . . .
H4 H 0.283265 0.136226 0.474921 0.020 Uiso 1 1 calc R U . . .
C5 C 0.24503(9) 0.0126(3) 0.36452(14) 0.0164(5) Uani 1 1 d . . . . .
C6 C 0.25451(9) -0.0619(3) 0.28888(13) 0.0164(5) Uani 1 1 d . . . . .
H6 H 0.226079 -0.110880 0.247413 0.020 Uiso 1 1 calc R U . . .
C7 C 0.30402(9) -0.0656(3) 0.27347(14) 0.0172(5) Uani 1 1 d . . . . .
H7 H 0.309066 -0.115856 0.221066 0.021 Uiso 1 1 calc R U . . .
C8 C 0.19301(9) 0.0263(3) 0.38284(14) 0.0188(5) Uani 1 1 d . . . . .
H8 H 0.190378 0.080923 0.435641 0.023 Uiso 1 1 calc R U . . .
C9 C 0.14868(9) -0.0320(3) 0.33121(15) 0.0208(5) Uani 1 1 d . . . . .
H9 H 0.152229 -0.090926 0.279884 0.025 Uiso 1 1 calc R U . . .
C10 C 0.09534(9) -0.0153(3) 0.34473(14) 0.0183(5) Uani 1 1 d . . . . .
C11 C 0.08224(9) 0.0868(3) 0.41047(15) 0.0204(5) Uani 1 1 d . . . . .
H11 H 0.108764 0.152805 0.448625 0.024 Uiso 1 1 calc R U . . .
C12 C 0.03108(10) 0.0928(3) 0.42057(15) 0.0235(6) Uani 1 1 d . . . . .
H12 H 0.022800 0.162834 0.465694 0.028 Uiso 1 1 calc R U . . .
C13 C -0.00829(10) -0.0018(3) 0.36577(15) 0.0250(6) Uani 1 1 d . . . . .
H13 H -0.043308 0.001724 0.373667 0.030 Uiso 1 1 calc R U . . .
C14 C 0.00375(10) -0.1016(3) 0.29948(15) 0.0248(6) Uani 1 1 d . . . . .
H14 H -0.023021 -0.166649 0.261383 0.030 Uiso 1 1 calc R U . . .
C15 C 0.05477(9) -0.1064(3) 0.28875(14) 0.0207(5) Uani 1 1 d . . . . .
H15 H 0.062521 -0.173137 0.242229 0.025 Uiso 1 1 calc R U . . .
C16 C 0.44535(9) 0.0330(3) 0.36355(14) 0.0181(5) Uani 1 1 d . . . . .
H16 H 0.444556 0.082062 0.418324 0.022 Uiso 1 1 calc R U . . .
C17 C 0.49665(9) 0.0167(3) 0.34200(14) 0.0166(5) Uani 1 1 d . . . . .
C18 C 0.50455(9) -0.0591(3) 0.26525(14) 0.0170(5) Uani 1 1 d . . . . .
H18 H 0.475552 -0.107220 0.224646 0.020 Uiso 1 1 calc R U . . .
C19 C 0.55388(9) -0.0642(3) 0.24833(13) 0.0161(5) Uani 1 1 d . . . . .
H19 H 0.558189 -0.114746 0.195542 0.019 Uiso 1 1 calc R U . . .
C20 C 0.59803(9) 0.0027(3) 0.30649(13) 0.0147(5) Uani 1 1 d . . . . .
C21 C 0.59012(9) 0.0795(3) 0.38254(14) 0.0179(5) Uani 1 1 d . . . . .
H21 H 0.619118 0.128432 0.422853 0.022 Uiso 1 1 calc R U . . .
C22 C 0.54078(9) 0.0850(3) 0.39976(13) 0.0166(5) Uani 1 1 d . . . . .
H22 H 0.536510 0.136690 0.452334 0.020 Uiso 1 1 calc R U . . .
C23 C 0.64962(9) -0.0162(3) 0.28526(14) 0.0186(5) Uani 1 1 d . . . . .
H23 H 0.650049 -0.063187 0.229966 0.022 Uiso 1 1 calc R U . . .
C24 C 0.69573(9) 0.0258(3) 0.33536(14) 0.0186(5) Uani 1 1 d . . . . .
H24 H 0.695514 0.067745 0.391613 0.022 Uiso 1 1 calc R U . . .
C25 C 0.74684(9) 0.0137(3) 0.31256(14) 0.0169(5) Uani 1 1 d . . . . .
C26 C 0.75346(9) -0.0595(3) 0.23463(14) 0.0174(5) Uani 1 1 d . . . . .
H26 H 0.724347 -0.111988 0.195894 0.021 Uiso 1 1 calc R U . . .
C27 C 0.80218(9) -0.0558(3) 0.21372(14) 0.0172(5) Uani 1 1 d . . . . .
H27 H 0.806089 -0.105118 0.160472 0.021 Uiso 1 1 calc R U . . .
C28 C 0.84520(9) 0.0186(3) 0.26919(14) 0.0205(5) Uani 1 1 d . . . . .
H28 H 0.878378 0.021855 0.253956 0.025 Uiso 1 1 calc R U . . .
C29 C 0.83949(9) 0.0886(3) 0.34747(14) 0.0201(5) Uani 1 1 d . . . . .
H29 H 0.868897 0.139025 0.386370 0.024 Uiso 1 1 calc R U . . .
C30 C 0.79100(9) 0.0848(3) 0.36855(15) 0.0202(5) Uani 1 1 d . . . . .
H30 H 0.787589 0.131746 0.422516 0.024 Uiso 1 1 calc R U . . .
C31 C 0.48534(9) 0.0409(3) 0.02374(14) 0.0167(5) Uani 1 1 d . . . . .
H31 H 0.502863 0.121700 0.066883 0.020 Uiso 1 1 calc R U . . .
C32 C 0.42878(9) 0.0179(3) 0.01564(13) 0.0148(5) Uani 1 1 d . . . . .
C33 C 0.40593(9) 0.0983(3) 0.07785(13) 0.0161(5) Uani 1 1 d . . . . .
H33 H 0.427392 0.166751 0.122534 0.019 Uiso 1 1 calc R U . . .
C34 C 0.35313(9) 0.0809(3) 0.07613(13) 0.0157(5) Uani 1 1 d . . . . .
H34 H 0.338904 0.137329 0.119413 0.019 Uiso 1 1 calc R U . . .
C35 C 0.32025(9) -0.0188(3) 0.01146(13) 0.0138(5) Uani 1 1 d . . . . .
C36 C 0.34288(9) -0.0997(3) -0.05080(13) 0.0161(5) Uani 1 1 d . . . . .
H36 H 0.321463 -0.168936 -0.095231 0.019 Uiso 1 1 calc R U . . .
C37 C 0.39599(9) -0.0810(3) -0.04903(13) 0.0153(5) Uani 1 1 d . . . . .
H37 H 0.410229 -0.136438 -0.092551 0.018 Uiso 1 1 calc R U . . .
C38 C 0.26368(9) -0.0409(3) 0.00458(14) 0.0179(5) Uani 1 1 d . . . . .
H38 H 0.245948 -0.126126 -0.036156 0.021 Uiso 1 1 calc R U . . .
C39 C 0.23509(9) 0.0474(3) 0.05020(14) 0.0183(5) Uani 1 1 d . . . . .
H39 H 0.253194 0.133295 0.090201 0.022 Uiso 1 1 calc R U . . .
C40 C 0.17856(9) 0.0277(3) 0.04593(14) 0.0167(5) Uani 1 1 d . . . . .
C41 C 0.15796(9) 0.1145(3) 0.10860(14) 0.0172(5) Uani 1 1 d . . . . .
H41 H 0.180217 0.188179 0.150034 0.021 Uiso 1 1 calc R U . . .
C42 C 0.10601(9) 0.0957(3) 0.11160(14) 0.0193(5) Uani 1 1 d . . . . .
H42 H 0.092847 0.155238 0.155226 0.023 Uiso 1 1 calc R U . . .
C43 C 0.07290(9) -0.0093(3) 0.05160(14) 0.0212(5) Uani 1 1 d . . . . .
H43 H 0.037216 -0.024339 0.054697 0.025 Uiso 1 1 calc R U . . .
C44 C 0.09188(9) -0.0927(3) -0.01331(14) 0.0197(5) Uani 1 1 d . . . . .
H44 H 0.068960 -0.162005 -0.055858 0.024 Uiso 1 1 calc R U . . .
C45 C 0.14431(9) -0.0748(3) -0.01591(14) 0.0195(5) Uani 1 1 d . . . . .
H45 H 0.157200 -0.132836 -0.060226 0.023 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.460(3) . ?
C1 C16 1.338(3) . ?
C2 C3 1.404(3) . ?
C2 C7 1.403(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.365(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.403(3) . ?
C5 C6 1.397(3) . ?
C5 C8 1.454(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.368(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.335(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.460(3) . ?
C10 C11 1.395(3) . ?
C10 C15 1.399(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.459(3) . ?
C17 C18 1.402(3) . ?
C17 C22 1.400(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.373(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.400(3) . ?
C20 C21 1.395(3) . ?
C20 C23 1.466(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.375(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.326(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.461(3) . ?
C25 C26 1.401(3) . ?
C25 C30 1.396(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.384(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.381(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.389(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.380(3) . ?
C30 H30 0.9500 . ?
C31 C31 1.335(4) 3_655 ?
C31 H31 0.9500 . ?
C31 C32 1.463(3) . ?
C32 C33 1.398(3) . ?
C32 C37 1.394(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.378(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.398(3) . ?
C35 C36 1.397(3) . ?
C35 C38 1.465(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.387(3) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C38 C39 1.325(3) . ?
C39 H39 0.9500 . ?
C39 C40 1.469(3) . ?
C40 C41 1.393(3) . ?
C40 C45 1.400(3) . ?
C41 H41 0.9500 . ?
C41 C42 1.374(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.379(3) . ?
C43 H43 0.9500 . ?
C43 C44 1.388(3) . ?
C44 H44 0.9500 . ?
C44 C45 1.384(3) . ?
C45 H45 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
C2 C1 H1 116.7 . . ?
C16 C1 H1 116.7 . . ?
C16 C1 C2 126.6(2) . . ?
C3 C2 C1 124.8(2) . . ?
C7 C2 C1 118.1(2) . . ?
C7 C2 C3 117.1(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 118.8 . . ?
C3 C4 C5 122.4(2) . . ?
C5 C4 H4 118.8 . . ?
C4 C5 C8 119.6(2) . . ?
C6 C5 C4 116.8(2) . . ?
C6 C5 C8 123.5(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.2(2) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 H7 119.1 . . ?
C6 C7 C2 121.9(2) . . ?
C6 C7 H7 119.1 . . ?
C5 C8 H8 117.5 . . ?
C9 C8 C5 125.1(2) . . ?
C9 C8 H8 117.5 . . ?
C8 C9 H9 116.3 . . ?
C8 C9 C10 127.3(2) . . ?
C10 C9 H9 116.3 . . ?
C11 C10 C9 123.8(2) . . ?
C11 C10 C15 117.7(2) . . ?
C15 C10 C9 118.5(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14 120.1 . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.6(2) . . ?
C14 C15 H15 119.2 . . ?
C1 C16 H16 117.1 . . ?
C1 C16 C17 125.8(2) . . ?
C17 C16 H16 117.1 . . ?
C18 C17 C16 123.9(2) . . ?
C22 C17 C16 118.6(2) . . ?
C22 C17 C18 117.4(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.0 . . ?
C18 C19 C20 122.0(2) . . ?
C20 C19 H19 119.0 . . ?
C19 C20 C23 118.47(19) . . ?
C21 C20 C19 117.5(2) . . ?
C21 C20 C23 124.0(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.7(2) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 H22 119.1 . . ?
C21 C22 C17 121.9(2) . . ?
C21 C22 H22 119.1 . . ?
C20 C23 H23 116.7 . . ?
C24 C23 C20 126.6(2) . . ?
C24 C23 H23 116.7 . . ?
C23 C24 H24 116.8 . . ?
C23 C24 C25 126.4(2) . . ?
C25 C24 H24 116.8 . . ?
C26 C25 C24 122.9(2) . . ?
C30 C25 C24 119.2(2) . . ?
C30 C25 C26 117.8(2) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.4(2) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 119.5 . . ?
C28 C27 C26 120.9(2) . . ?
C28 C27 H27 119.5 . . ?
C27 C28 H28 120.3 . . ?
C27 C28 C29 119.4(2) . . ?
C29 C28 H28 120.3 . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.8(2) . . ?
C30 C29 H29 120.1 . . ?
C25 C30 H30 119.2 . . ?
C29 C30 C25 121.6(2) . . ?
C29 C30 H30 119.2 . . ?
C31 C31 H31 116.9 3_655 . ?
C31 C31 C32 126.2(3) 3_655 . ?
C32 C31 H31 116.9 . . ?
C33 C32 C31 117.90(19) . . ?
C37 C32 C31 124.7(2) . . ?
C37 C32 C33 117.4(2) . . ?
C32 C33 H33 119.1 . . ?
C34 C33 C32 121.8(2) . . ?
C34 C33 H33 119.1 . . ?
C33 C34 H34 119.6 . . ?
C33 C34 C35 120.8(2) . . ?
C35 C34 H34 119.6 . . ?
C34 C35 C38 123.9(2) . . ?
C36 C35 C34 117.6(2) . . ?
C36 C35 C38 118.4(2) . . ?
C35 C36 H36 119.3 . . ?
C37 C36 C35 121.3(2) . . ?
C37 C36 H36 119.3 . . ?
C32 C37 H37 119.5 . . ?
C36 C37 C32 121.0(2) . . ?
C36 C37 H37 119.5 . . ?
C35 C38 H38 117.1 . . ?
C39 C38 C35 125.7(2) . . ?
C39 C38 H38 117.1 . . ?
C38 C39 H39 116.3 . . ?
C38 C39 C40 127.4(2) . . ?
C40 C39 H39 116.3 . . ?
C41 C40 C39 117.6(2) . . ?
C41 C40 C45 117.9(2) . . ?
C45 C40 C39 124.4(2) . . ?
C40 C41 H41 119.4 . . ?
C42 C41 C40 121.2(2) . . ?
C42 C41 H41 119.4 . . ?
C41 C42 H42 119.8 . . ?
C41 C42 C43 120.4(2) . . ?
C43 C42 H42 119.8 . . ?
C42 C43 H43 120.1 . . ?
C42 C43 C44 119.8(2) . . ?
C44 C43 H43 120.1 . . ?
C43 C44 H44 120.1 . . ?
C45 C44 C43 119.8(2) . . ?
C45 C44 H44 120.1 . . ?
C40 C45 H45 119.6 . . ?
C44 C45 C40 120.9(2) . . ?
C44 C45 H45 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -177.1(2) . . . . ?
C1 C2 C7 C6 177.0(2) . . . . ?
C1 C16 C17 C18 -2.5(4) . . . . ?
C1 C16 C17 C22 175.5(2) . . . . ?
C2 C1 C16 C17 -179.0(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C2 C7 C6 -1.6(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C3 C4 C5 C8 -178.0(2) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C4 C5 C8 C9 178.3(2) . . . . ?
C5 C6 C7 C2 0.8(3) . . . . ?
C5 C8 C9 C10 -177.3(2) . . . . ?
C6 C5 C8 C9 1.0(4) . . . . ?
C7 C2 C3 C4 1.3(3) . . . . ?
C8 C5 C6 C7 177.6(2) . . . . ?
C8 C9 C10 C11 8.5(4) . . . . ?
C8 C9 C10 C15 -171.5(2) . . . . ?
C9 C10 C11 C12 -178.4(2) . . . . ?
C9 C10 C15 C14 177.8(2) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C10 C15 C14 -2.3(3) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C13 C14 C15 C10 1.4(4) . . . . ?
C15 C10 C11 C12 1.6(3) . . . . ?
C16 C1 C2 C3 2.3(4) . . . . ?
C16 C1 C2 C7 -176.1(2) . . . . ?
C16 C17 C18 C19 177.8(2) . . . . ?
C16 C17 C22 C21 -177.9(2) . . . . ?
C17 C18 C19 C20 0.9(3) . . . . ?
C18 C17 C22 C21 0.2(3) . . . . ?
C18 C19 C20 C21 -1.4(3) . . . . ?
C18 C19 C20 C23 177.0(2) . . . . ?
C19 C20 C21 C22 1.3(3) . . . . ?
C19 C20 C23 C24 -174.2(2) . . . . ?
C20 C21 C22 C17 -0.8(3) . . . . ?
C20 C23 C24 C25 -177.3(2) . . . . ?
C21 C20 C23 C24 4.1(4) . . . . ?
C22 C17 C18 C19 -0.3(3) . . . . ?
C23 C20 C21 C22 -177.0(2) . . . . ?
C23 C24 C25 C26 -5.3(4) . . . . ?
C23 C24 C25 C30 171.8(2) . . . . ?
C24 C25 C26 C27 175.4(2) . . . . ?
C24 C25 C30 C29 -175.3(2) . . . . ?
C25 C26 C27 C28 0.5(3) . . . . ?
C26 C25 C30 C29 1.9(3) . . . . ?
C26 C27 C28 C29 0.8(3) . . . . ?
C27 C28 C29 C30 -0.6(3) . . . . ?
C28 C29 C30 C25 -0.7(4) . . . . ?
C30 C25 C26 C27 -1.8(3) . . . . ?
C31 C31 C32 C33 172.4(3) 3_655 . . . ?
C31 C31 C32 C37 -6.5(4) 3_655 . . . ?
C31 C32 C33 C34 -178.8(2) . . . . ?
C31 C32 C37 C36 178.4(2) . . . . ?
C32 C33 C34 C35 0.0(3) . . . . ?
C33 C32 C37 C36 -0.5(3) . . . . ?
C33 C34 C35 C36 0.1(3) . . . . ?
C33 C34 C35 C38 -179.0(2) . . . . ?
C34 C35 C36 C37 -0.4(3) . . . . ?
C34 C35 C38 C39 9.5(4) . . . . ?
C35 C36 C37 C32 0.7(3) . . . . ?
C35 C38 C39 C40 -179.2(2) . . . . ?
C36 C35 C38 C39 -169.5(2) . . . . ?
C37 C32 C33 C34 0.2(3) . . . . ?
C38 C35 C36 C37 178.7(2) . . . . ?
C38 C39 C40 C41 170.6(2) . . . . ?
C38 C39 C40 C45 -8.2(4) . . . . ?
C39 C40 C41 C42 -176.8(2) . . . . ?
C39 C40 C45 C44 177.2(2) . . . . ?
C40 C41 C42 C43 -0.6(3) . . . . ?
C41 C40 C45 C44 -1.6(3) . . . . ?
C41 C42 C43 C44 -1.5(3) . . . . ?
C42 C43 C44 C45 2.0(3) . . . . ?
C43 C44 C45 C40 -0.4(3) . . . . ?
C45 C40 C41 C42 2.1(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.900
_oxdiff_exptl_absorpt_empirical_full_min 0.761
