# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_bey_1030
_database_code_depnum_ccdc_archive 'CCDC 2165148'
loop_
_audit_author_name
_audit_author_address
'Masaru Tanioka'
;AICHI GAKUIN University
Japan
;
_audit_update_record             
;
2022-04-07 deposited with the CCDC.	2022-06-15 downloaded from the CCDC.
;
_audit_creation_date             2020-10-30
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'bridged eosin Y'
_chemical_name_systematic        'bridged eosin Y'
_chemical_formula_moiety         'C20 H7 Br3 O5'
_chemical_formula_sum            'C20 H7 Br3 O5'
_chemical_formula_weight         566.99
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C40 H10 Br6 O10 '
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 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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   7.9825(4)
_cell_length_b                   9.6307(5)
_cell_length_c                   12.1546(6)
_cell_angle_alpha                68.286(5)
_cell_angle_beta                 76.020(4)
_cell_angle_gamma                83.671(4)
_cell_volume                     842.17(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4026
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      68.0090
_cell_measurement_theta_min      4.9440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.196
_exptl_absorpt_correction_T_max  0.895
_exptl_absorpt_correction_T_min  0.447
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    2.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -3 4 0.0825
2 -5 -5 0.0632
-1 -3 -8 0.0497
-3 4 -1 0.0528
-1 5 6 0.0403
4 4 0 0.0038
-2 4 5 0.0422
4 -4 0 0.0672
2 3 8 0.0431
-1 -4 4 0.0571
-4 -3 1 0.0229
-4 -5 -5 0.0323
-5 0 0 0.0340

_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.033
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
3.1847 -2.7668 4.0562 -0.2252 -0.9384 0.2620
1.5327 -5.1165 -4.7994 -0.0238 -0.1089 0.9938
-1.1928 -2.5315 -7.8834 0.1641 0.6746 0.7198
-3.0829 4.2700 -1.0875 0.1824 0.7643 -0.6185
-0.7487 4.6944 6.2599 -0.0374 -0.1456 -0.9886
4.0549 3.5199 -0.0401 -0.9722 0.2339 -0.0089
-1.7844 4.4147 5.4367 0.1394 -0.0360 -0.9896
3.7715 -3.7387 0.0048 -0.3745 -0.6072 0.7008
2.2180 3.0427 7.6601 -0.3877 -0.6349 -0.6683
-0.9605 -3.8769 3.5511 0.5649 -0.8231 0.0576
-4.1614 -3.0034 0.5903 0.9682 -0.2327 -0.0920
-3.7995 -4.5711 -4.5025 0.8720 0.1600 0.4627
-4.9394 -0.0127 0.4960 0.8754 0.1629 -0.4552

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6805
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.408
_diffrn_reflns_theta_min         4.011
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  42.00   0.50    0.24    --   41.13 -37.00  60.00  102
  2  ω     12.00  62.00   0.50    0.24    --   41.13 -63.00 120.00  100
  3  ω     41.00  72.00   0.50    0.24    --   41.13-104.00  90.00   62
  4  ω     31.00  57.00   0.50    0.95    --   95.43 -50.00 120.00   52
  5  ω     72.00 101.00   0.50    0.95    --   95.43 -77.00  90.00   58
  6  ω     38.00  68.00   0.50    0.24    --   41.13 -91.00 -30.00   60
  7  ω     39.00  76.00   0.50    0.95    --   95.43 -80.00-137.00   74
  8  ω     41.00  67.00   0.50    0.95    --   95.43 -59.00-120.00   52
  9  ω     29.00  55.00   0.50    0.95    --   95.43 -50.00-150.00   52
 10  ω     29.00  54.00   0.50    0.95    --   95.43 -50.00 -90.00   50
 11  ω     36.00  94.00   0.50    0.95    --   95.43-117.00 -60.00  116
 12  ω     69.00  94.00   0.50    0.24    --   41.13-138.00-150.00   50
 13  ω     21.00  46.00   0.50    0.24    --   41.13-138.00-150.00   50
 14  ω    -26.00  33.00   0.50    0.24    --   41.13 -91.00 -30.00  118
 15  ω     30.00  73.00   0.50    0.95    --   95.43 -77.00  60.00   86
 16  ω     11.00  37.00   0.50    0.24    --   41.13-104.00  90.00   52
 17  ω    -20.00  29.00   0.50    0.24    --  -41.44  12.00  90.00   98
 18  ω    -18.00  12.00   0.50    0.24    --  -41.44  80.00 -13.00   60
 19  ω    -51.00 -26.00   0.50    0.24    --  -41.44  80.00 -13.00   50
 20  ω    -66.00 -41.00   0.50    0.95    --  -95.75  59.00 -30.00   50
 21  ω    -57.00 -32.00   0.50    0.95    --  -95.75  50.00   0.00   50
 22  ω    -61.00 -35.00   0.50    0.95    --  -95.75 117.00  60.00   52
 23  ω    -57.00 -31.00   0.50    0.95    --  -95.75  50.00 120.00   52
 24  ω    -22.00  13.00   0.50    0.24    --  -41.44  37.00 120.00   70
 25  ω     49.00  87.00   0.50    0.24    --   41.13  80.00 -13.00   76
 26  ω     79.00 142.00   0.50    0.95    --   95.43  42.00 -30.00  126
 27  ω    128.00 161.00   0.50    0.95    --   95.43  68.00  60.00   66
 28  ω    123.00 148.00   0.50    0.95    --   95.43  77.00 120.00   50
 29  ω     94.00 120.00   0.50    0.95    --   95.43  68.00  60.00   52
 30  ω     82.00 117.00   0.50    0.95    --   95.43  80.00 -13.00   70
 31  ω     69.00 106.00   0.50    0.95    --   95.43  77.00 120.00   74
 32  ω    -28.00  39.00   0.50    0.24    --   41.13 -80.00-137.00  134
 33  ω    -18.00  26.00   0.50    0.24    --   41.13 -25.00-150.00   88
 34  ω     82.00 163.00   0.50    0.95    --   95.43  33.00-180.00  162
 35  ω    -57.00 -32.00   0.50    0.95    --  -95.75  50.00-180.00   50
 36  ω    -83.00 -29.00   0.50    0.95    --  -95.75  68.00-180.00  108
 37  ω    -97.00 -30.00   0.50    0.95    --  -95.75 117.00 -30.00  134
 38  ω    -97.00 -65.00   0.50    0.95    --  -95.75 117.00  60.00   64
 39  ω    -92.00 -67.00   0.50    0.95    --  -95.75  80.00 -13.00   50
 40  ω   -104.00 -32.00   0.50    0.95    --  -95.75 117.00 -60.00  144
 41  ω   -125.00 -35.00   0.50    0.95    --  -95.75 141.00 -30.15  180
 42  ω   -106.00 -29.00   0.50    0.95    --  -95.75 117.00 150.00  154
 43  ω   -125.00 -27.00   0.50    0.95    --  -95.75 145.00 150.00  196
 44  ω    -96.00 -71.00   0.50    0.95    --  -95.75 -17.00 120.00   50
 45  ω   -110.00 -79.00   0.50    0.95    --  -95.75 -42.00  90.00   62
 46  ω    -56.00 -29.00   0.50    0.24    --  -41.44 -50.00 120.00   54
 47  ω   -104.00 -76.00   0.50    0.24    --  -41.44 -50.00 120.00   56
 48  ω    -96.00 -71.00   0.50    0.24    --  -41.44-138.00 120.00   50
 49  ω   -156.00-113.00   0.50    0.95    --  -95.75 -42.00  90.00   86
 50  ω   -161.00-116.00   0.50    0.95    --  -95.75 -17.00 120.00   90
 51  ω   -145.00 -84.00   0.50    0.95    --  -95.75 -96.00 -90.00  122
 52  ω   -112.00 -84.00   0.50    0.95    --  -95.75 -80.00-137.00   56
 53  ω   -110.00 -73.00   0.50    0.24    --  -41.44 -80.00-137.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1740421000
_diffrn_orient_matrix_UB_12      -0.0753729000
_diffrn_orient_matrix_UB_13      0.0297260000
_diffrn_orient_matrix_UB_21      -0.0449559000
_diffrn_orient_matrix_UB_22      0.1169180000
_diffrn_orient_matrix_UB_23      -0.1163081000
_diffrn_orient_matrix_UB_31      0.0852317000
_diffrn_orient_matrix_UB_32      -0.1015431000
_diffrn_orient_matrix_UB_33      -0.0715902000
_diffrn_oxdiff_digest_frames     
;
014c042441cbf784b05a58b8aa6e2b3b76042949a36
;
_diffrn_oxdiff_digest_hkl        
;
01907412a1eb38ad94eff3f063f7698015342f
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2788
_reflns_number_total             3051
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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         0.685
_refine_diff_density_min         -1.012
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.105
_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)+(0.0651P)²+0.2908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1055
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C16(H16), C15(H15), C17(H17), C5(H5A)
2.b Idealised tetrahedral OH refined as rotating group:
 O5(H5), O2(H2)
;
_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
Br3 Br 1.00770(5) -0.05855(4) 0.22157(4) 0.02644(15) Uani 1 1 d . . . . .
Br1 Br 0.93879(5) 0.32816(4) -0.09052(3) 0.02651(15) Uani 1 1 d . . . . .
Br2 Br 0.56195(6) 0.85190(4) -0.05115(4) 0.03007(15) Uani 1 1 d . . . . .
O1 O 0.7917(4) 0.2166(3) 0.1725(2) 0.0230(6) Uani 1 1 d . . . . .
O3 O 0.7159(4) -0.0702(3) 0.6601(2) 0.0262(6) Uani 1 1 d . . . . .
O5 O 0.5028(4) 0.1297(3) 0.7005(2) 0.0260(6) Uani 1 1 d . . . . .
H5 H 0.565684 0.052128 0.716937 0.039 Uiso 1 1 calc GR . . . .
O2 O 0.8054(4) 0.6437(3) -0.1781(2) 0.0276(6) Uani 1 1 d . . . . .
H2 H 0.767055 0.732020 -0.203184 0.041 Uiso 1 1 calc GR . . . .
O4 O 0.9458(4) -0.1734(3) 0.5020(3) 0.0274(6) Uani 1 1 d . . . . .
C3 C 0.7416(5) 0.5807(4) -0.0587(3) 0.0225(8) Uani 1 1 d . . . . .
C18 C 0.2914(5) 0.3735(4) 0.6194(4) 0.0216(7) Uani 1 1 d . . . . .
H18 H 0.283143 0.324345 0.704102 0.026 Uiso 1 1 calc R . . . .
C16 C 0.1900(5) 0.5593(4) 0.4539(4) 0.0226(8) Uani 1 1 d . . . . .
H16 H 0.114746 0.641548 0.425012 0.027 Uiso 1 1 calc R . . . .
C15 C 0.3008(5) 0.5053(4) 0.3724(4) 0.0222(7) Uani 1 1 d . . . . .
H15 H 0.294065 0.545321 0.289475 0.027 Uiso 1 1 calc R . . . .
C19 C 0.4110(5) 0.3212(4) 0.5371(3) 0.0211(7) Uani 1 1 d . . . . .
C7 C 0.5598(5) 0.3429(4) 0.3258(3) 0.0213(8) Uani 1 1 d . . . . .
C9 C 0.6295(5) 0.1331(4) 0.5020(3) 0.0201(7) Uani 1 1 d . . . . .
C14 C 0.4246(5) 0.3912(4) 0.4098(3) 0.0193(7) Uani 1 1 d . . . . .
C13 C 0.7704(5) 0.1477(4) 0.2939(3) 0.0220(8) Uani 1 1 d . . . . .
C17 C 0.1857(5) 0.4962(4) 0.5777(4) 0.0227(8) Uani 1 1 d . . . . .
H17 H 0.111211 0.536873 0.632617 0.027 Uiso 1 1 calc R . . . .
C20 C 0.5179(5) 0.1908(4) 0.5812(3) 0.0224(8) Uani 1 1 d . . . . .
C8 C 0.6508(5) 0.2108(4) 0.3739(4) 0.0212(7) Uani 1 1 d . . . . .
C1 C 0.7281(5) 0.3592(4) 0.1250(3) 0.0203(7) Uani 1 1 d . . . . .
C12 C 0.8621(5) 0.0177(4) 0.3338(3) 0.0216(7) Uani 1 1 d . . . . .
C5 C 0.5725(5) 0.5788(4) 0.1381(3) 0.0207(7) Uani 1 1 d . . . . .
H5A H 0.501375 0.632789 0.184194 0.025 Uiso 1 1 calc R . . . .
C10 C 0.7289(5) -0.0019(4) 0.5491(4) 0.0229(8) Uani 1 1 d . . . . .
C11 C 0.8564(5) -0.0634(4) 0.4608(4) 0.0232(8) Uani 1 1 d . . . . .
C2 C 0.7893(5) 0.4316(4) 0.0003(3) 0.0218(8) Uani 1 1 d . . . . .
C4 C 0.6321(5) 0.6503(4) 0.0157(3) 0.0230(8) Uani 1 1 d . . . . .
C6 C 0.6142(5) 0.4279(4) 0.1969(3) 0.0205(7) 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
Br3 C12 1.881(4) . ?
Br1 C2 1.884(4) . ?
Br2 C4 1.886(4) . ?
O1 C13 1.351(5) . ?
O1 C1 1.371(5) . ?
O3 C10 1.247(5) . ?
O5 C20 1.328(5) . ?
O2 C3 1.339(4) . ?
O4 C11 1.223(5) . ?
C3 C2 1.404(5) . ?
C3 C4 1.404(5) . ?
C18 C19 1.405(5) . ?
C18 C17 1.382(6) . ?
C16 C15 1.375(5) . ?
C16 C17 1.392(6) . ?
C15 C14 1.414(5) . ?
C19 C14 1.422(5) . ?
C19 C20 1.442(5) . ?
C7 C14 1.460(5) . ?
C7 C8 1.392(5) . ?
C7 C6 1.454(5) . ?
C9 C20 1.379(6) . ?
C9 C8 1.432(5) . ?
C9 C10 1.445(5) . ?
C13 C8 1.445(5) . ?
C13 C12 1.364(5) . ?
C1 C2 1.399(6) . ?
C1 C6 1.393(5) . ?
C12 C11 1.441(6) . ?
C5 C4 1.373(5) . ?
C5 C6 1.405(5) . ?
C10 C11 1.532(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 C1 120.2(3) . . ?
O2 C3 C2 118.2(3) . . ?
O2 C3 C4 126.3(4) . . ?
C4 C3 C2 115.6(3) . . ?
C17 C18 C19 120.3(4) . . ?
C15 C16 C17 121.5(4) . . ?
C16 C15 C14 121.2(4) . . ?
C18 C19 C14 121.1(3) . . ?
C18 C19 C20 120.0(4) . . ?
C14 C19 C20 118.8(3) . . ?
C8 C7 C14 117.6(3) . . ?
C8 C7 C6 117.6(3) . . ?
C6 C7 C14 124.7(3) . . ?
C20 C9 C8 119.6(3) . . ?
C20 C9 C10 119.6(3) . . ?
C8 C9 C10 120.7(3) . . ?
C15 C14 C19 116.3(3) . . ?
C15 C14 C7 123.6(3) . . ?
C19 C14 C7 120.0(3) . . ?
O1 C13 C8 119.6(3) . . ?
O1 C13 C12 116.8(3) . . ?
C12 C13 C8 123.5(4) . . ?
C18 C17 C16 118.9(3) . . ?
O5 C20 C19 117.0(3) . . ?
O5 C20 C9 122.2(3) . . ?
C9 C20 C19 120.8(3) . . ?
C7 C8 C9 122.1(3) . . ?
C7 C8 C13 120.0(4) . . ?
C9 C8 C13 117.9(3) . . ?
O1 C1 C2 115.3(3) . . ?
O1 C1 C6 122.1(3) . . ?
C6 C1 C2 122.6(3) . . ?
C13 C12 Br3 120.0(3) . . ?
C13 C12 C11 122.3(3) . . ?
C11 C12 Br3 117.7(3) . . ?
C4 C5 C6 121.6(3) . . ?
O3 C10 C9 122.2(3) . . ?
O3 C10 C11 118.3(3) . . ?
C9 C10 C11 119.5(3) . . ?
O4 C11 C12 125.5(3) . . ?
O4 C11 C10 118.7(4) . . ?
C12 C11 C10 115.8(3) . . ?
C3 C2 Br1 119.2(3) . . ?
C1 C2 Br1 119.7(3) . . ?
C1 C2 C3 121.1(3) . . ?
C3 C4 Br2 120.0(3) . . ?
C5 C4 Br2 116.9(3) . . ?
C5 C4 C3 123.1(4) . . ?
C1 C6 C7 118.1(3) . . ?
C1 C6 C5 115.8(3) . . ?
C5 C6 C7 125.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.530
_oxdiff_exptl_absorpt_empirical_full_min 0.769
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/Et2O'
####################################################################### 
# 
# 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_exp_108
_database_code_depnum_ccdc_archive 'CCDC 2165151'
loop_
_audit_author_name
_audit_author_address
'Masaru Tanioka'
;AICHI GAKUIN University
Japan
;
_audit_update_record             
;
2022-04-07 deposited with the CCDC.	2022-06-15 downloaded from the CCDC.
;
_audit_creation_date             2021-03-20
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            9-(4-nitrophenyl)anthracene
_chemical_name_systematic        9-(4-nitrophenyl)anthracene
_chemical_formula_moiety         'C20 H13 N O2'
_chemical_formula_sum            'C20 H13 N O2'
_chemical_formula_weight         299.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C160 H104 N8 O16 '
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 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.1681(5)
_cell_length_b                   8.0980(2)
_cell_length_c                   22.3810(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.728(3)
_cell_angle_gamma                90
_cell_volume                     2896.39(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5361
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      68.0800
_cell_measurement_theta_min      4.0110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.337
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
9 -3 -2 0.2767
4 -4 7 0.3130
-1 -3 11 0.3382
-9 2 4 0.3074
-3 4 -8 0.4307
9 0 -10 0.2153
-8 0 -7 0.2194
1 5 -4 0.5050
8 0 7 0.1854
8 3 4 0.3239
-7 -4 -2 0.3752
8 -1 8 0.2155
1 -5 6 0.3653
-8 -2 -5 0.2947
0 0 14 0.1620
0 0 -14 0.1818
5 -5 -4 0.3535
5 -5 0 0.3359
-4 4 8 0.3533
2 -3 11 0.2673
-10 0 1 0.1954
10 -1 0 0.1895
10 0 -1 0.1776
10 2 -4 0.2958
4 4 -8 0.4510
3 3 9 0.2977
1 -5 1 0.3588
-1 -5 -3 0.3593
-4 -3 -10 0.2912
-1 0 -14 0.1776
4 3 -12 0.3667
10 0 -4 0.1813
10 0 2 0.1686
-8 0 11 0.2429
-4 -2 13 0.3063

_exptl_crystal_size_max          0.886
_exptl_crystal_size_mid          0.383
_exptl_crystal_size_min          0.351
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
8.8465 -2.8319 -1.5963 -0.1630 -0.6850 0.7101
4.0420 -3.9447 6.8922 -0.0066 -0.0384 0.9992
-0.7953 -3.4803 10.8822 0.1102 0.4485 0.8870
-9.4122 2.2039 4.0245 0.1941 0.8126 -0.5495
-2.7577 3.9199 -8.2347 -0.0269 -0.1011 -0.9945
8.8639 -0.0780 -9.5335 -0.2339 -0.9722 0.0090
-8.2139 -0.1219 -7.2068 -0.6327 0.4841 -0.6044
0.8728 5.0204 -4.3051 0.4192 -0.3247 -0.8479
8.2998 0.4412 6.9602 0.6617 -0.5065 0.5528
7.5959 3.0689 3.6710 0.7929 -0.6090 0.0205
-6.6311 -3.8797 -1.9889 -0.7766 0.5972 0.2008
7.5804 -1.1010 7.8798 0.4986 -0.3806 0.7788
0.8852 -4.7894 5.6400 -0.2694 0.2099 0.9399
-8.1910 -2.0925 -5.1908 -0.7695 0.5903 -0.2437
-0.1814 -0.0712 14.3870 0.7264 0.3955 0.5621
0.2855 -0.0371 -14.4062 -0.7375 -0.4015 -0.5430
4.5125 -4.6449 -3.6517 -0.6210 -0.3348 0.7087
4.5203 -4.7255 0.3549 -0.4244 -0.2277 0.8764
-4.0422 4.0744 8.0400 0.7911 0.4278 -0.4371
2.4626 -2.7741 11.2150 0.3117 0.1716 0.9345
-10.4654 -0.0431 1.1448 -0.2608 0.8855 -0.3845
10.2523 -0.6895 0.2816 0.2382 -0.8101 0.5357
10.4488 -0.0936 -0.8810 0.2572 -0.8734 0.4136
9.7169 1.7822 -4.4034 0.2835 -0.9587 -0.0216
3.6051 4.1084 -8.2433 0.1869 -0.6259 -0.7572
3.3455 3.4638 9.0689 0.9914 -0.1310 -0.0027
1.3418 -5.1879 1.2450 -0.5307 0.0681 0.8448
-0.6088 -5.0990 -3.2757 -0.8111 0.1058 0.5753
-4.0406 -2.5769 -10.3688 -0.9706 0.1288 -0.2033
-0.6720 -0.1226 -14.1779 -0.7650 -0.3149 -0.5618
3.8653 2.6829 -11.9690 -0.1715 -0.7054 -0.6877
10.3795 -0.1466 -4.2463 0.0754 -0.9548 0.2874
10.0049 -0.0314 2.2357 0.4119 -0.7569 0.5074
-7.8464 -0.0608 11.1699 0.3317 0.9361 0.1168
-3.6892 -2.3673 12.5579 0.2458 0.6977 0.6729

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7070
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.143
_diffrn_reflns_theta_min         3.997
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  24.00   0.50    0.20    --  -41.44  21.00  30.00   98
  2  ω    -53.00  -4.00   0.50    0.20    --  -41.44  55.00  58.00   98
  3  ω    -53.00 -28.00   0.50    0.33    --  -95.43 117.00  90.00   50
  4  ω    -57.00 -32.00   0.50    0.33    --  -95.43  55.00  58.00   50
  5  ω    -57.00 -32.00   0.50    0.33    --  -95.43  50.00 150.00   50
  6  ω    -77.00 -27.00   0.50    0.33    --  -95.43  68.00  60.00  100
  7  ω   -100.00 -72.00   0.50    0.33    --  -95.43 117.00  90.00   56
  8  ω    -55.00 -29.00   0.50    0.33    --  -95.43  50.00-120.00   52
  9  ω    -81.00 -29.00   0.50    0.20    --  -41.44 -55.00 -84.00  104
 10  ω     23.00  55.00   0.50    0.20    --   41.75  55.00  58.00   64
 11  ω     59.00  91.00   0.50    0.20    --   41.75  55.00  58.00   64
 12  ω     95.00 120.00   0.50    0.33    --   95.75  55.00  58.00   50
 13  ω     95.00 163.00   0.50    0.33    --   95.75  33.00  30.00  136
 14  ω     71.00 106.00   0.50    0.20    --   41.75 138.00 -90.00   70
 15  ω     25.00 102.00   0.50    0.20    --   41.75  43.00-120.00  154
 16  ω     29.00  56.00   0.50    0.33    --   95.75 -55.00 -84.00   54
 17  ω     39.00  65.00   0.50    0.33    --   95.75 -59.00 -60.00   52
 18  ω     37.00  63.00   0.50    0.33    --   95.75 -59.00 -30.00   52
 19  ω     33.00  59.00   0.50    0.33    --   95.75 -59.00 -90.00   52
 20  ω     31.00  56.00   0.50    0.33    --   95.75 -50.00-120.00   50
 21  ω     29.00  54.00   0.50    0.33    --   95.75 -50.00-150.00   50
 22  ω     29.00  54.00   0.50    0.33    --   95.75 -50.00-180.00   50
 23  ω     35.00  60.00   0.50    0.20    --   41.75 -55.00 -84.00   50
 24  ω     85.00 110.00   0.50    0.33    --   95.75-117.00 -60.00   50
 25  ω     29.00  55.00   0.50    0.33    --   95.75-117.00 -60.00   52
 26  ω     29.00  57.00   0.50    0.33    --   95.75 -50.00 -60.00   56
 27  ω    -14.00  18.00   0.50    0.20    --   41.75 -11.00-150.00   64
 28  ω    -21.00   4.00   0.50    0.20    --   41.75 -55.00 -84.00   50
 29  ω     -9.00  20.00   0.50    0.20    --   41.75 -21.00  90.00   58
 30  ω     43.00  69.00   0.50    0.33    --   95.75 -59.00 150.00   52
 31  ω     38.00  64.00   0.50    0.33    --   95.75 -59.00 120.00   52
 32  ω     29.00  54.00   0.50    0.33    --   95.75 -50.00 120.00   50
 33  ω    -28.00  11.00   0.50    0.20    --   41.75 -21.00 150.00   78
 34  ω   -112.00 -85.00   0.50    0.33    --  -95.43 -50.00 150.00   54
 35  ω   -160.00-134.00   0.50    0.33    --  -95.43 -50.00 150.00   52
 36  ω   -158.00 -84.00   0.50    0.33    --  -95.43 -50.00 -30.00  148
 37  ω   -163.00 -95.00   0.50    0.33    --  -95.43 -55.00 -84.00  136
 38  ω   -164.00 -74.00   0.50    0.33    --  -95.43 -17.00-180.00  180
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0300504000
_diffrn_orient_matrix_UB_12      0.1224145000
_diffrn_orient_matrix_UB_13      0.0514749000
_diffrn_orient_matrix_UB_21      -0.0816189000
_diffrn_orient_matrix_UB_22      -0.0279108000
_diffrn_orient_matrix_UB_23      0.0263209000
_diffrn_orient_matrix_UB_31      0.0415810000
_diffrn_orient_matrix_UB_32      -0.1427637000
_diffrn_orient_matrix_UB_33      0.0388870000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2515
_reflns_number_total             2635
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.00084(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2635
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.068
_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)+(0.0430P)²+1.7649P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0883
_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:
 C009(H009), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N)
;
_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
O001 O 0.13748(6) 0.94362(11) 0.51607(4) 0.0386(3) Uani 1 1 d . . . . .
O002 O 0.07322(6) 0.78592(12) 0.44630(4) 0.0429(3) Uani 1 1 d . . . . .
N1 N 0.11947(6) 0.80707(12) 0.49420(5) 0.0277(2) Uani 1 1 d . . . . .
C004 C 0.23823(7) 0.00469(14) 0.69327(5) 0.0221(2) Uani 1 1 d . . . . .
C005 C 0.25642(7) 0.24163(14) 0.62789(5) 0.0214(2) Uani 1 1 d . . . . .
C006 C 0.37572(7) 0.06272(14) 0.66662(5) 0.0229(3) Uani 1 1 d . . . . .
C007 C 0.34241(7) 0.20450(13) 0.63248(5) 0.0219(2) Uani 1 1 d . . . . .
C008 C 0.20349(7) 0.14351(14) 0.65796(5) 0.0214(2) Uani 1 1 d . . . . .
C009 C 0.39926(7) 0.30231(14) 0.60409(5) 0.0241(3) Uani 1 1 d . . . . .
H009 H 0.378940 0.396858 0.581349 0.029 Uiso 1 1 calc R U . . .
C00A C 0.15569(7) 0.66159(14) 0.52781(5) 0.0233(3) Uani 1 1 d . . . . .
C00B C 0.32292(7) -0.03300(14) 0.69641(5) 0.0233(3) Uani 1 1 d . . . . .
H00B H 0.345167 -0.125882 0.719342 0.028 Uiso 1 1 calc R U . . .
C00C C 0.22156(7) 0.38923(14) 0.59245(5) 0.0218(2) Uani 1 1 d . . . . .
C00D C 0.11640(7) 0.17836(14) 0.65702(5) 0.0237(3) Uani 1 1 d . . . . .
H00D H 0.091626 0.268237 0.633533 0.028 Uiso 1 1 calc R U . . .
C00E C 0.24487(7) 0.54876(14) 0.61221(5) 0.0237(3) Uani 1 1 d . . . . .
H00E H 0.283669 0.563096 0.648198 0.028 Uiso 1 1 calc R U . . .
C00F C 0.18518(7) -0.09080(14) 0.72543(5) 0.0251(3) Uani 1 1 d . . . . .
H00F H 0.207616 -0.183766 0.748229 0.030 Uiso 1 1 calc R U . . .
C00G C 0.13134(7) 0.50601(15) 0.50654(5) 0.0259(3) Uani 1 1 d . . . . .
H00G H 0.092781 0.492715 0.470365 0.031 Uiso 1 1 calc R U . . .
C00H C 0.16466(7) 0.36969(14) 0.53935(5) 0.0250(3) Uani 1 1 d . . . . .
H00H H 0.148561 0.261797 0.525528 0.030 Uiso 1 1 calc R U . . .
C00I C 0.48164(8) 0.26250(15) 0.60907(5) 0.0272(3) Uani 1 1 d . . . . .
H00I H 0.518096 0.330274 0.590198 0.033 Uiso 1 1 calc R U . . .
C00J C 0.21221(7) 0.68631(14) 0.58005(5) 0.0243(3) Uani 1 1 d . . . . .
H00J H 0.228174 0.794604 0.593484 0.029 Uiso 1 1 calc R U . . .
C00K C 0.46241(7) 0.02444(15) 0.66982(5) 0.0268(3) Uani 1 1 d . . . . .
H00K H 0.484471 -0.070218 0.691747 0.032 Uiso 1 1 calc R U . . .
C00L C 0.06854(7) 0.08544(15) 0.68903(5) 0.0273(3) Uani 1 1 d . . . . .
H00L H 0.011127 0.112087 0.688031 0.033 Uiso 1 1 calc R U . . .
C00M C 0.10347(8) -0.05139(15) 0.72405(5) 0.0278(3) Uani 1 1 d . . . . .
H00M H 0.069495 -0.115055 0.746453 0.033 Uiso 1 1 calc R U . . .
C00N C 0.51404(8) 0.12077(16) 0.64213(5) 0.0291(3) Uani 1 1 d . . . . .
H00N H 0.571638 0.093482 0.644850 0.035 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
O001 N1 1.2263(13) . ?
O002 N1 1.2225(14) . ?
N1 C00A 1.4707(14) . ?
C004 C008 1.4384(15) . ?
C004 C00B 1.3942(16) . ?
C004 C00F 1.4279(16) . ?
C005 C007 1.4109(16) . ?
C005 C008 1.4112(16) . ?
C005 C00C 1.4965(15) . ?
C006 C007 1.4377(15) . ?
C006 C00B 1.3954(16) . ?
C006 C00K 1.4266(16) . ?
C007 C009 1.4329(16) . ?
C008 C00D 1.4330(16) . ?
C009 H009 0.9500 . ?
C009 C00I 1.3585(17) . ?
C00A C00G 1.3827(16) . ?
C00A C00J 1.3849(16) . ?
C00B H00B 0.9500 . ?
C00C C00E 1.3986(16) . ?
C00C C00H 1.3971(16) . ?
C00D H00D 0.9500 . ?
C00D C00L 1.3589(17) . ?
C00E H00E 0.9500 . ?
C00E C00J 1.3864(16) . ?
C00F H00F 0.9500 . ?
C00F C00M 1.3549(17) . ?
C00G H00G 0.9500 . ?
C00G C00H 1.3886(16) . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
C00I C00N 1.4219(18) . ?
C00J H00J 0.9500 . ?
C00K H00K 0.9500 . ?
C00K C00N 1.3589(18) . ?
C00L H00L 0.9500 . ?
C00L C00M 1.4236(17) . ?
C00M H00M 0.9500 . ?
C00N H00N 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
O001 N1 C00A 117.79(10) . . ?
O002 N1 O001 123.57(10) . . ?
O002 N1 C00A 118.65(10) . . ?
C00B C004 C008 119.83(10) . . ?
C00B C004 C00F 121.09(10) . . ?
C00F C004 C008 119.07(10) . . ?
C007 C005 C008 120.49(10) . . ?
C007 C005 C00C 119.77(10) . . ?
C008 C005 C00C 119.70(10) . . ?
C00B C006 C007 119.38(10) . . ?
C00B C006 C00K 121.53(10) . . ?
C00K C006 C007 119.09(10) . . ?
C005 C007 C006 119.64(10) . . ?
C005 C007 C009 122.76(10) . . ?
C009 C007 C006 117.60(10) . . ?
C005 C008 C004 119.18(10) . . ?
C005 C008 C00D 123.21(10) . . ?
C00D C008 C004 117.58(10) . . ?
C007 C009 H009 119.4 . . ?
C00I C009 C007 121.29(11) . . ?
C00I C009 H009 119.4 . . ?
C00G C00A N1 118.90(10) . . ?
C00G C00A C00J 122.64(10) . . ?
C00J C00A N1 118.46(10) . . ?
C004 C00B C006 121.44(10) . . ?
C004 C00B H00B 119.3 . . ?
C006 C00B H00B 119.3 . . ?
C00E C00C C005 120.56(10) . . ?
C00H C00C C005 120.45(10) . . ?
C00H C00C C00E 118.99(10) . . ?
C008 C00D H00D 119.3 . . ?
C00L C00D C008 121.33(11) . . ?
C00L C00D H00D 119.3 . . ?
C00C C00E H00E 119.5 . . ?
C00J C00E C00C 120.99(10) . . ?
C00J C00E H00E 119.5 . . ?
C004 C00F H00F 119.4 . . ?
C00M C00F C004 121.27(11) . . ?
C00M C00F H00F 119.4 . . ?
C00A C00G H00G 120.8 . . ?
C00A C00G C00H 118.35(10) . . ?
C00H C00G H00G 120.8 . . ?
C00C C00H H00H 119.6 . . ?
C00G C00H C00C 120.83(11) . . ?
C00G C00H H00H 119.6 . . ?
C009 C00I H00I 119.6 . . ?
C009 C00I C00N 120.89(11) . . ?
C00N C00I H00I 119.6 . . ?
C00A C00J C00E 118.21(10) . . ?
C00A C00J H00J 120.9 . . ?
C00E C00J H00J 120.9 . . ?
C006 C00K H00K 119.4 . . ?
C00N C00K C006 121.28(11) . . ?
C00N C00K H00K 119.4 . . ?
C00D C00L H00L 119.6 . . ?
C00D C00L C00M 120.75(11) . . ?
C00M C00L H00L 119.6 . . ?
C00F C00M C00L 119.99(11) . . ?
C00F C00M H00M 120.0 . . ?
C00L C00M H00M 120.0 . . ?
C00I C00N H00N 120.1 . . ?
C00K C00N C00I 119.83(11) . . ?
C00K C00N H00N 120.1 . . ?

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
O001 N1 C00A C00G 175.07(11) . . . . ?
O001 N1 C00A C00J -4.16(16) . . . . ?
O002 N1 C00A C00G -4.83(16) . . . . ?
O002 N1 C00A C00J 175.94(11) . . . . ?
N1 C00A C00G C00H -178.68(10) . . . . ?
N1 C00A C00J C00E 178.73(10) . . . . ?
C004 C008 C00D C00L 1.02(16) . . . . ?
C004 C00F C00M C00L 1.35(18) . . . . ?
C005 C007 C009 C00I -179.54(10) . . . . ?
C005 C008 C00D C00L -176.71(10) . . . . ?
C005 C00C C00E C00J -179.28(10) . . . . ?
C005 C00C C00H C00G 179.33(10) . . . . ?
C006 C007 C009 C00I 0.16(16) . . . . ?
C006 C00K C00N C00I -0.16(18) . . . . ?
C007 C005 C008 C004 -0.18(15) . . . . ?
C007 C005 C008 C00D 177.51(10) . . . . ?
C007 C005 C00C C00E -66.83(14) . . . . ?
C007 C005 C00C C00H 113.69(12) . . . . ?
C007 C006 C00B C004 0.74(16) . . . . ?
C007 C006 C00K C00N 1.08(17) . . . . ?
C007 C009 C00I C00N 0.77(17) . . . . ?
C008 C004 C00B C006 0.94(16) . . . . ?
C008 C004 C00F C00M -1.11(16) . . . . ?
C008 C005 C007 C006 1.86(16) . . . . ?
C008 C005 C007 C009 -178.45(10) . . . . ?
C008 C005 C00C C00E 111.26(12) . . . . ?
C008 C005 C00C C00H -68.22(14) . . . . ?
C008 C00D C00L C00M -0.81(17) . . . . ?
C009 C00I C00N C00K -0.78(18) . . . . ?
C00A C00G C00H C00C -0.19(17) . . . . ?
C00B C004 C008 C005 -1.23(15) . . . . ?
C00B C004 C008 C00D -179.05(10) . . . . ?
C00B C004 C00F C00M 177.86(11) . . . . ?
C00B C006 C007 C005 -2.14(15) . . . . ?
C00B C006 C007 C009 178.15(10) . . . . ?
C00B C006 C00K C00N -178.12(11) . . . . ?
C00C C005 C007 C006 179.93(9) . . . . ?
C00C C005 C007 C009 -0.38(16) . . . . ?
C00C C005 C008 C004 -178.26(9) . . . . ?
C00C C005 C008 C00D -0.56(16) . . . . ?
C00C C00E C00J C00A 0.10(17) . . . . ?
C00D C00L C00M C00F -0.39(18) . . . . ?
C00E C00C C00H C00G -0.16(17) . . . . ?
C00F C004 C008 C005 177.75(10) . . . . ?
C00F C004 C008 C00D -0.07(15) . . . . ?
C00F C004 C00B C006 -178.02(10) . . . . ?
C00G C00A C00J C00E -0.48(17) . . . . ?
C00H C00C C00E C00J 0.20(17) . . . . ?
C00J C00A C00G C00H 0.52(17) . . . . ?
C00K C006 C007 C005 178.64(10) . . . . ?
C00K C006 C007 C009 -1.07(15) . . . . ?
C00K C006 C00B C004 179.94(10) . . . . ?

_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 1.223
_oxdiff_exptl_absorpt_empirical_full_min 0.850
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_exp_98
_database_code_depnum_ccdc_archive 'CCDC 2165150'
loop_
_audit_author_name
_audit_author_address
'Masaru Tanioka'
;AICHI GAKUIN University
Japan
;
_audit_update_record             
;
2022-04-07 deposited with the CCDC.	2022-06-15 downloaded from the CCDC.
;
_audit_creation_date             2021-02-16
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            1-(4-nitrophenyl)pyrene
_chemical_name_systematic        1-(4-nitrophenyl)pyrene
_chemical_formula_moiety         'C22 H13 N O2'
_chemical_formula_sum            'C22 H13 N O2'
_chemical_formula_weight         323.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C88 H52 N4 O8 '
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 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.6037(4)
_cell_length_b                   11.9960(5)
_cell_length_c                   13.4769(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.696(4)
_cell_angle_gamma                90
_cell_volume                     1538.63(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3726
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      68.2740
_cell_measurement_theta_min      3.3220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 3 8 0.0715
0 0 -9 0.1064
1 -8 1 0.0296
-4 3 6 0.0609
-5 -1 -3 0.0444
5 2 4 0.0442
6 0 1 0.0723
0 -3 -8 0.1030
-3 4 -5 0.0497
-1 -7 -1 0.0337
2 7 -3 0.0600
-5 1 6 0.0649
4 -2 6 0.0478
-4 6 3 0.0540
-1 8 0 0.0362
3 7 1 0.0379
3 6 -1 0.0391

_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.071
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
-0.1677 2.7458 8.1468 -0.0640 0.0713 0.9954
-0.0462 -0.3965 -8.6519 0.2589 -0.3000 -0.9181
0.6917 -7.6539 1.1057 -0.6170 0.7243 -0.3077
-4.4060 2.9157 6.0350 0.6007 0.3237 0.7310
-5.3464 -1.1067 -3.2831 0.7744 0.4213 -0.4720
4.8074 1.5967 4.3259 -0.7023 -0.3825 0.6004
6.0359 0.0778 1.0310 -0.8628 -0.4684 0.1900
0.4129 -3.4554 -7.8322 -0.0251 -0.0108 -0.9996
-3.3533 4.0312 -5.1261 0.8841 -0.3127 -0.3472
-1.4834 -7.4722 -1.0332 -0.2360 0.8030 -0.5472
1.9088 6.8654 -3.4627 0.2830 -0.9576 0.0534
-5.2015 0.5663 5.7178 0.5717 0.6038 0.5555
3.8784 -2.2459 5.5748 -0.8578 0.1146 0.5010
-3.9735 5.6963 2.8337 0.8201 -0.1070 0.5621
-1.3007 7.5896 -0.3842 0.6740 -0.6390 0.3707
2.9128 6.6819 1.3170 -0.0209 -0.8344 0.5508
3.4201 6.4989 -1.1104 -0.0248 -0.9549 0.2959

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7975
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.171
_diffrn_reflns_theta_min         4.956
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  28.00   0.50    1.66    --  -41.44  21.00 -90.00   88
  2  ω    -17.00  20.00   0.50    1.66    --  -41.44  87.00-178.00   74
  3  ω    -24.00   3.00   0.50    1.66    --  -41.44  11.00-180.00   54
  4  ω      6.00  32.00   0.50    1.66    --  -41.44  11.00-180.00   52
  5  ω    -21.00   5.00   0.50    1.66    --   41.75 -21.00 -60.00   52
  6  ω    -26.00  18.00   0.50    1.66    --   41.75 -11.00 -90.00   88
  7  ω    -26.00  23.00   0.50    1.66    --   41.75 -11.00-180.00   98
  8  ω     29.00  54.00   0.50    6.66    --   95.75 -50.00 -90.00   50
  9  ω     46.00  79.00   0.50    6.66    --   95.75 -68.00 -60.00   66
 10  ω     29.00  55.00   0.50    6.66    --   95.75 -50.00 -30.00   52
 11  ω     40.00  83.00   0.50    6.66    --   95.75 -87.00  64.00   86
 12  ω     31.00  56.00   0.50    6.66    --   95.75 -50.00  60.00   50
 13  ω     28.00  53.00   0.50    6.66    --   95.75 -59.00  60.00   50
 14  ω     19.00  72.00   0.50    1.66    --   41.75 -87.00  64.00  106
 15  ω    -26.00  -1.00   0.50    1.66    --   41.75 -87.00  64.00   50
 16  ω    -33.00  18.00   0.50    1.66    --  -41.44  32.00 120.00  102
 17  ω    -57.00 -32.00   0.50    6.66    --  -95.43  50.00  30.00   50
 18  ω    -57.00 -32.00   0.50    6.66    --  -95.43  50.00   0.00   50
 19  ω   -106.00 -27.00   0.50    6.66    --  -95.43  77.00  30.00  158
 20  ω    -83.00 -29.00   0.50    6.66    --  -95.43  68.00 150.00  108
 21  ω   -144.00-118.00   0.50    6.66    --  -95.43 -87.00  64.00   52
 22  ω   -148.00 -89.00   0.50    6.66    --  -95.43 -86.00  30.00  118
 23  ω   -102.00 -77.00   0.50    1.66    --  -41.44-138.00 -30.00   50
 24  ω   -159.00 -77.00   0.50    6.66    --  -95.43 -68.00-120.00  164
 25  ω    -57.00 -31.00   0.50    6.66    --  -95.43  50.00-180.00   52
 26  ω    -52.00 -27.00   0.50    6.66    --  -95.43  59.00-180.00   50
 27  ω    -68.00 -25.00   0.50    6.66    --  -95.43  87.00-178.00   86
 28  ω    -52.00 -27.00   0.50    1.66    --  -41.44  87.00-178.00   50
 29  ω     81.00 107.00   0.50    1.66    --   41.75 138.00 -60.00   52
 30  ω     64.00  89.00   0.50    1.66    --   41.75 138.00-150.00   50
 31  ω    124.00 155.00   0.50    6.66    --   95.75  87.00-178.00   62
 32  ω     79.00 104.00   0.50    6.66    --   95.75  87.00-178.00   50
 33  ω    -20.00   6.00   0.50    1.66    --   41.75 -11.00-120.00   52
 34  ω     79.00 162.00   0.50    6.66    --   95.75  68.00 120.00  166
 35  ω    -79.00 -48.00   0.50    6.66    --  -95.43  68.00-180.00   62
 36  ω   -107.00 -72.00   0.50    6.66    --  -95.43  87.00-178.00   70
 37  ω   -160.00 -86.00   0.50    6.66    --  -95.43 -33.00 150.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1382838000
_diffrn_orient_matrix_UB_12      0.0634805000
_diffrn_orient_matrix_UB_13      -0.0320925000
_diffrn_orient_matrix_UB_21      -0.0831196000
_diffrn_orient_matrix_UB_22      -0.0964342000
_diffrn_orient_matrix_UB_23      0.0395392000
_diffrn_orient_matrix_UB_31      0.0130821000
_diffrn_orient_matrix_UB_32      0.0563285000
_diffrn_orient_matrix_UB_33      0.1034683000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2356
_reflns_number_total             2792
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2792
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.068
_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)+(0.0882P)²+0.3592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1442
_refine_ls_wR_factor_ref         0.1513
_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:
 C004(H004), C007(H007), C009(H009), C00D(H00D), C00F(H00F), C00G(H00G),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P)
;
_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
O001 O 1.20231(13) 0.85170(12) 0.53402(9) 0.0540(4) Uani 1 1 d . . . . .
O002 O 1.25293(15) 0.71716(14) 0.43871(12) 0.0717(5) Uani 1 1 d . . . . .
N1 N 1.17318(15) 0.78911(13) 0.46210(11) 0.0471(4) Uani 1 1 d . . . . .
C004 C 0.56266(17) 0.65160(15) 0.26809(13) 0.0430(4) Uani 1 1 d . . . . .
H004 H 0.649538 0.639636 0.309425 0.052 Uiso 1 1 calc R U . . .
C005 C 1.03585(17) 0.80174(14) 0.40131(12) 0.0408(4) Uani 1 1 d . . . . .
C006 C 0.77819(17) 0.82798(15) 0.28704(12) 0.0419(4) Uani 1 1 d . . . . .
C007 C 0.80986(17) 0.88541(14) 0.37701(12) 0.0428(4) Uani 1 1 d . . . . .
H007 H 0.742091 0.934198 0.398690 0.051 Uiso 1 1 calc R U . . .
C008 C 0.53876(17) 0.75684(14) 0.21719(12) 0.0409(4) Uani 1 1 d . . . . .
C009 C 0.93812(17) 0.87235(14) 0.43490(12) 0.0425(4) Uani 1 1 d . . . . .
H009 H 0.959183 0.910972 0.496624 0.051 Uiso 1 1 calc R U . . .
C00A C 0.30339(17) 0.68770(17) 0.14944(12) 0.0481(5) Uani 1 1 d . . . . .
C00B C 0.63830(17) 0.84262(15) 0.22586(13) 0.0440(4) Uani 1 1 d . . . . .
C00C C 0.33230(17) 0.58376(17) 0.19820(13) 0.0480(4) Uani 1 1 d . . . . .
C00D C 1.00842(18) 0.74344(15) 0.31217(13) 0.0460(4) Uani 1 1 d . . . . .
H00D H 1.076943 0.695287 0.290613 0.055 Uiso 1 1 calc R U . . .
C00E C 0.40565(17) 0.77393(16) 0.15762(12) 0.0449(4) Uani 1 1 d . . . . .
C00F C 0.46568(18) 0.56932(16) 0.25903(13) 0.0479(4) Uani 1 1 d . . . . .
H00F H 0.486050 0.500904 0.293430 0.057 Uiso 1 1 calc R U . . .
C00G C 0.87897(17) 0.75715(16) 0.25554(13) 0.0466(4) Uani 1 1 d . . . . .
H00G H 0.858051 0.717818 0.194177 0.056 Uiso 1 1 calc R U . . .
C00H C 0.37580(19) 0.87704(17) 0.10768(13) 0.0518(5) Uani 1 1 d . . . . .
C00I C 0.16990(18) 0.7045(2) 0.09065(13) 0.0575(5) Uani 1 1 d . . . . .
C00J C 0.6052(2) 0.94372(16) 0.17666(15) 0.0548(5) Uani 1 1 d . . . . .
H00J H 0.672071 1.002487 0.183547 0.066 Uiso 1 1 calc R U . . .
C00K C 0.2304(2) 0.4995(2) 0.18717(15) 0.0605(6) Uani 1 1 d . . . . .
H00K H 0.250026 0.429814 0.219499 0.073 Uiso 1 1 calc R U . . .
C00L C 0.1415(2) 0.8089(2) 0.04227(15) 0.0673(7) Uani 1 1 d . . . . .
H00L H 0.052133 0.821093 0.004241 0.081 Uiso 1 1 calc R U . . .
C00M C 0.4772(2) 0.95998(18) 0.11822(15) 0.0605(5) Uani 1 1 d . . . . .
H00M H 0.458371 1.029132 0.084736 0.073 Uiso 1 1 calc R U . . .
C00N C 0.0725(2) 0.6175(3) 0.08308(16) 0.0708(7) Uani 1 1 d . . . . .
H00N H -0.016786 0.627950 0.044499 0.085 Uiso 1 1 calc R U . . .
C00O C 0.2380(2) 0.8911(2) 0.04891(15) 0.0660(6) Uani 1 1 d . . . . .
H00O H 0.215820 0.959421 0.014723 0.079 Uiso 1 1 calc R U . . .
C00P C 0.1031(2) 0.5163(3) 0.13047(17) 0.0708(7) Uani 1 1 d . . . . .
H00P H 0.035248 0.458259 0.123547 0.085 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
O001 N1 1.2283(19) . ?
O002 N1 1.223(2) . ?
N1 C005 1.464(2) . ?
C004 H004 0.9500 . ?
C004 C008 1.440(2) . ?
C004 C00F 1.351(2) . ?
C005 C009 1.385(2) . ?
C005 C00D 1.384(2) . ?
C006 C007 1.392(2) . ?
C006 C00B 1.490(2) . ?
C006 C00G 1.396(2) . ?
C007 H007 0.9500 . ?
C007 C009 1.376(2) . ?
C008 C00B 1.399(2) . ?
C008 C00E 1.430(2) . ?
C009 H009 0.9500 . ?
C00A C00C 1.419(3) . ?
C00A C00E 1.420(3) . ?
C00A C00I 1.428(2) . ?
C00B C00J 1.398(3) . ?
C00C C00F 1.436(2) . ?
C00C C00K 1.401(3) . ?
C00D H00D 0.9500 . ?
C00D C00G 1.379(2) . ?
C00E C00H 1.419(3) . ?
C00F H00F 0.9500 . ?
C00G H00G 0.9500 . ?
C00H C00M 1.386(3) . ?
C00H C00O 1.458(3) . ?
C00I C00L 1.421(4) . ?
C00I C00N 1.396(3) . ?
C00J H00J 0.9500 . ?
C00J C00M 1.382(3) . ?
C00K H00K 0.9500 . ?
C00K C00P 1.367(3) . ?
C00L H00L 0.9500 . ?
C00L C00O 1.348(3) . ?
C00M H00M 0.9500 . ?
C00N H00N 0.9500 . ?
C00N C00P 1.385(4) . ?
C00O H00O 0.9500 . ?
C00P H00P 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
O001 N1 C005 118.11(15) . . ?
O002 N1 O001 123.40(15) . . ?
O002 N1 C005 118.49(14) . . ?
C008 C004 H004 118.9 . . ?
C00F C004 H004 118.9 . . ?
C00F C004 C008 122.22(16) . . ?
C009 C005 N1 118.65(14) . . ?
C00D C005 N1 119.06(15) . . ?
C00D C005 C009 122.29(16) . . ?
C007 C006 C00B 119.96(15) . . ?
C007 C006 C00G 119.10(15) . . ?
C00G C006 C00B 120.94(15) . . ?
C006 C007 H007 119.6 . . ?
C009 C007 C006 120.80(15) . . ?
C009 C007 H007 119.6 . . ?
C00B C008 C004 122.78(15) . . ?
C00B C008 C00E 119.40(16) . . ?
C00E C008 C004 117.80(15) . . ?
C005 C009 H009 120.7 . . ?
C007 C009 C005 118.61(15) . . ?
C007 C009 H009 120.7 . . ?
C00C C00A C00E 120.89(15) . . ?
C00C C00A C00I 119.10(18) . . ?
C00E C00A C00I 120.00(19) . . ?
C008 C00B C006 121.01(15) . . ?
C00J C00B C006 119.72(16) . . ?
C00J C00B C008 119.27(16) . . ?
C00A C00C C00F 118.33(16) . . ?
C00K C00C C00A 119.61(18) . . ?
C00K C00C C00F 122.05(19) . . ?
C005 C00D H00D 120.9 . . ?
C00G C00D C005 118.21(16) . . ?
C00G C00D H00D 120.9 . . ?
C00A C00E C008 119.72(17) . . ?
C00H C00E C008 119.98(16) . . ?
C00H C00E C00A 120.29(16) . . ?
C004 C00F C00C 120.99(17) . . ?
C004 C00F H00F 119.5 . . ?
C00C C00F H00F 119.5 . . ?
C006 C00G H00G 119.5 . . ?
C00D C00G C006 120.98(15) . . ?
C00D C00G H00G 119.5 . . ?
C00E C00H C00O 118.01(19) . . ?
C00M C00H C00E 118.86(17) . . ?
C00M C00H C00O 123.12(19) . . ?
C00L C00I C00A 118.81(19) . . ?
C00N C00I C00A 118.5(2) . . ?
C00N C00I C00L 122.67(19) . . ?
C00B C00J H00J 119.3 . . ?
C00M C00J C00B 121.41(19) . . ?
C00M C00J H00J 119.3 . . ?
C00C C00K H00K 119.6 . . ?
C00P C00K C00C 120.8(2) . . ?
C00P C00K H00K 119.6 . . ?
C00I C00L H00L 119.1 . . ?
C00O C00L C00I 121.74(18) . . ?
C00O C00L H00L 119.1 . . ?
C00H C00M H00M 119.5 . . ?
C00J C00M C00H 121.06(19) . . ?
C00J C00M H00M 119.5 . . ?
C00I C00N H00N 119.2 . . ?
C00P C00N C00I 121.55(19) . . ?
C00P C00N H00N 119.2 . . ?
C00H C00O H00O 119.4 . . ?
C00L C00O C00H 121.1(2) . . ?
C00L C00O H00O 119.4 . . ?
C00K C00P C00N 120.4(2) . . ?
C00K C00P H00P 119.8 . . ?
C00N C00P H00P 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
O001 N1 C005 C009 -8.7(2) . . . . ?
O001 N1 C005 C00D 170.91(16) . . . . ?
O002 N1 C005 C009 171.42(16) . . . . ?
O002 N1 C005 C00D -9.0(2) . . . . ?
N1 C005 C009 C007 179.07(14) . . . . ?
N1 C005 C00D C00G -179.45(15) . . . . ?
C004 C008 C00B C006 1.8(2) . . . . ?
C004 C008 C00B C00J -177.87(15) . . . . ?
C004 C008 C00E C00A -0.8(2) . . . . ?
C004 C008 C00E C00H 178.66(15) . . . . ?
C005 C00D C00G C006 0.1(3) . . . . ?
C006 C007 C009 C005 0.7(2) . . . . ?
C006 C00B C00J C00M 179.19(17) . . . . ?
C007 C006 C00B C008 -109.40(19) . . . . ?
C007 C006 C00B C00J 70.2(2) . . . . ?
C007 C006 C00G C00D 0.1(3) . . . . ?
C008 C004 C00F C00C -0.6(2) . . . . ?
C008 C00B C00J C00M -1.2(3) . . . . ?
C008 C00E C00H C00M -0.3(3) . . . . ?
C008 C00E C00H C00O -179.18(15) . . . . ?
C009 C005 C00D C00G 0.1(3) . . . . ?
C00A C00C C00F C004 -1.4(2) . . . . ?
C00A C00C C00K C00P -0.4(3) . . . . ?
C00A C00E C00H C00M 179.18(16) . . . . ?
C00A C00E C00H C00O 0.3(2) . . . . ?
C00A C00I C00L C00O 1.3(3) . . . . ?
C00A C00I C00N C00P -0.4(3) . . . . ?
C00B C006 C007 C009 179.53(15) . . . . ?
C00B C006 C00G C00D -179.92(16) . . . . ?
C00B C008 C00E C00A -179.23(14) . . . . ?
C00B C008 C00E C00H 0.2(2) . . . . ?
C00B C00J C00M C00H 1.1(3) . . . . ?
C00C C00A C00E C008 -1.1(2) . . . . ?
C00C C00A C00E C00H 179.39(15) . . . . ?
C00C C00A C00I C00L 179.82(15) . . . . ?
C00C C00A C00I C00N -0.2(2) . . . . ?
C00C C00K C00P C00N -0.2(3) . . . . ?
C00D C005 C009 C007 -0.5(3) . . . . ?
C00E C008 C00B C006 -179.89(14) . . . . ?
C00E C008 C00B C00J 0.5(2) . . . . ?
C00E C00A C00C C00F 2.2(2) . . . . ?
C00E C00A C00C C00K -178.74(15) . . . . ?
C00E C00A C00I C00L -0.9(2) . . . . ?
C00E C00A C00I C00N 179.12(15) . . . . ?
C00E C00H C00M C00J -0.4(3) . . . . ?
C00E C00H C00O C00L 0.2(3) . . . . ?
C00F C004 C008 C00B -179.94(15) . . . . ?
C00F C004 C008 C00E 1.7(2) . . . . ?
C00F C00C C00K C00P 178.61(16) . . . . ?
C00G C006 C007 C009 -0.5(3) . . . . ?
C00G C006 C00B C008 70.6(2) . . . . ?
C00G C006 C00B C00J -109.8(2) . . . . ?
C00I C00A C00C C00F -178.45(14) . . . . ?
C00I C00A C00C C00K 0.6(2) . . . . ?
C00I C00A C00E C008 179.55(14) . . . . ?
C00I C00A C00E C00H 0.1(2) . . . . ?
C00I C00L C00O C00H -1.0(3) . . . . ?
C00I C00N C00P C00K 0.6(3) . . . . ?
C00K C00C C00F C004 179.62(16) . . . . ?
C00L C00I C00N C00P 179.60(18) . . . . ?
C00M C00H C00O C00L -178.70(19) . . . . ?
C00N C00I C00L C00O -178.66(18) . . . . ?
C00O C00H C00M C00J 178.45(18) . . . . ?

_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 1.362
_oxdiff_exptl_absorpt_empirical_full_min 0.697
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_exp_133
_database_code_depnum_ccdc_archive 'CCDC 2165152'
loop_
_audit_author_name
_audit_author_address
'Masaru Tanioka'
;AICHI GAKUIN University
Japan
;
_audit_update_record             
;
2022-04-07 deposited with the CCDC.	2022-06-15 downloaded from the CCDC.
;
_audit_creation_date             2021-04-13
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            1-(4-nitrophenyl)perylene
_chemical_name_systematic        1-(4-nitrophenyl)perylene
_chemical_formula_moiety         '2(C26 H15 N O2)'
_chemical_formula_sum            'C52 H30 N2 O4'
_chemical_formula_weight         746.78
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.1091(2)
_cell_length_b                   13.4501(2)
_cell_length_c                   43.2055(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7036.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13433
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      67.8910
_cell_measurement_theta_min      4.0980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
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            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3104
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -8 -2 0.1268
-7 1 -10 0.0691
-6 2 -19 0.0599
-3 -3 -25 0.0522
3 -7 -16 0.0974
-2 6 18 0.0957
0 -1 -28 0.0151
-6 5 -6 0.0731
6 6 -1 0.0776
8 -1 3 0.1028
1 0 28 0.0191
1 2 -27 0.0305
-2 -2 26 0.0509
-5 1 21 0.0653

_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.041
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
3.2363 -7.9303 -1.9739 -0.1170 -0.4953 0.8608
-7.2571 0.8193 -10.4352 -0.1306 -0.5339 -0.8354
-5.6164 1.5318 -18.9935 0.2396 -0.5844 -0.7753
-2.8445 -2.6814 -24.6834 0.3703 -0.8968 -0.2423
2.6904 -6.5040 -16.0437 0.3006 -0.7228 0.6223
-1.9412 6.2428 18.3295 -0.3285 0.7908 -0.5164
-0.0538 -0.8443 -27.9183 0.7200 -0.6844 -0.1152
-6.0463 5.2072 -6.4098 0.0419 -0.0432 -0.9982
5.8072 5.8662 -1.4728 0.6803 0.7167 0.1536
7.7812 -0.8364 2.8646 0.3696 0.3920 0.8424
0.6055 0.3399 27.9466 -0.7100 0.6738 0.2049
1.3799 2.4170 -26.5084 0.9249 -0.3276 -0.1931
-1.8583 -2.0398 26.4630 -0.9358 0.3316 0.1194
-5.0599 1.1445 21.1466 -0.8410 0.2995 -0.4506

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            37300
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.408
_diffrn_reflns_theta_min         4.093
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00  23.00   0.50    2.80    --   40.52 -12.00 -30.00  116
  2  ω     45.00  71.00   0.50    2.80    --   40.52  52.00 -68.00   52
  3  ω    128.00 160.00   0.50   11.20    --   96.04  52.00 -68.00   64
  4  ω    139.00 164.00   0.50   11.20    --   96.04 114.00   6.00   50
  5  ω     85.00 118.00   0.50   11.20    --   96.04  70.00 124.00   66
  6  ω     80.00 161.00   0.50   11.20    --   96.04 144.00 -30.00  162
  7  ω     82.00 119.00   0.50   11.20    --   96.04  52.00 -68.00   74
  8  ω     52.00  77.00   0.50   11.20    --   96.04 -70.00  -6.00   50
  9  ω     44.00  84.00   0.50    2.80    --   40.52-114.00 -84.00   80
 10  ω     52.00  77.00   0.50    2.80    --   40.52-171.00 134.00   50
 11  ω    -23.00  59.00   0.50    2.80    --   40.52 -70.00  -6.00  164
 12  ω     90.00 115.00   0.50   11.20    --   96.04-171.00 134.00   50
 13  ω     33.00  63.00   0.50   11.20    --   96.04 -59.00 150.00   60
 14  ω     28.00  53.00   0.50   11.20    --   96.04 -52.00 145.00   50
 15  ω     -4.00  60.00   0.50    2.80    --   40.52 -52.00 145.00  128
 16  ω    -24.00  41.00   0.50    2.80    --   40.52 -37.00  60.00  130
 17  ω     50.00  87.00   0.50    2.80    --   40.52  70.00 124.00   74
 18  ω    -24.00  28.00   0.50    2.80    --  -40.83  12.00 -60.00  104
 19  ω    -35.00  -2.00   0.50    2.80    --   40.52 -12.00  30.00   66
 20  ω    -20.00  23.00   0.50    2.80    --   40.52 -12.00 150.00   86
 21  ω    -44.00 -19.00   0.50    2.80    --  -40.83  70.00 124.00   50
 22  ω    -56.00 -31.00   0.50    2.80    --  -40.83 114.00   6.00   50
 23  ω    -57.00 -32.00   0.50   11.20    --  -96.35  52.00 -68.00   50
 24  ω    -57.00 -32.00   0.50   11.20    --  -96.35  50.00 -30.00   50
 25  ω    -68.00 -31.00   0.50   11.20    --  -96.35  59.00 -30.00   74
 26  ω    -56.00 -30.00   0.50   11.20    --  -96.35  50.00  60.00   52
 27  ω    -57.00 -31.00   0.50   11.20    --  -96.35  50.00  90.00   52
 28  ω    -56.00 -30.00   0.50   11.20    --  -96.35  50.00 120.00   52
 29  ω    -83.00 -29.00   0.50   11.20    --  -96.35  68.00 150.00  108
 30  ω    -76.00 -51.00   0.50    2.80    --  -40.83 171.00 148.00   50
 31  ω   -110.00 -29.00   0.50   11.20    --  -96.35 117.00 120.00  162
 32  ω    -46.00 -21.00   0.50    2.80    --  -40.83 -52.00 145.00   50
 33  ω    -72.00 -47.00   0.50    2.80    --  -40.83 -70.00  -6.00   50
 34  ω   -103.00 -78.00   0.50   11.20    --  -96.35-117.00-120.00   50
 35  ω   -130.00 -92.00   0.50   11.20    --  -96.35-114.00 -84.00   76
 36  ω   -124.00 -74.00   0.50   11.20    --  -96.35 -70.00  -6.00  100
 37  ω   -102.00 -77.00   0.50    2.80    --  -40.83-171.00 134.00   50
 38  ω   -165.00 -72.00   0.50   11.20    --  -96.35 -17.00   0.00  186
 39  ω   -126.00 -86.00   0.50   11.20    --  -96.35 -42.00-150.00   80
 40  ω   -161.00-135.00   0.50   11.20    --  -96.35 -42.00-150.00   52
 41  ω   -163.00-117.00   0.50   11.20    --  -96.35-117.00-120.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0626249000
_diffrn_orient_matrix_UB_12      0.0471094000
_diffrn_orient_matrix_UB_13      -0.0273346000
_diffrn_orient_matrix_UB_21      0.0506000000
_diffrn_orient_matrix_UB_22      0.0776194000
_diffrn_orient_matrix_UB_23      0.0220680000
_diffrn_orient_matrix_UB_31      0.0985339000
_diffrn_orient_matrix_UB_32      -0.0698380000
_diffrn_orient_matrix_UB_33      0.0060477000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5840
_reflns_number_total             6425
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.00016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         6425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      1.156
_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)+(0.0443P)²+7.5344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1410
_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:
 C12(H12), C52(H52), C36(H36), C13(H13), C54(H54), C31(H31), C15(H15),
 C32(H32), C34(H34), C23(H23), C24(H24), C53(H53), C6(H6), C7(H7), C29(H29),
 C41(H41), C16(H16), C35(H35), C5(H5), C27(H27), C3(H3), C25(H25), C56(H56),
 C2(H2), C42(H42), C44(H44), C58(H58), C45(H45), C28(H28), C57(H57)
;
_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
O19 O 0.73493(16) 0.84720(14) 0.22502(4) 0.0416(5) Uani 1 1 d . . . . .
O48 O 0.52134(18) 0.59106(16) 0.21093(4) 0.0514(5) Uani 1 1 d . . . . .
O47 O 0.34524(19) 0.59816(15) 0.20298(4) 0.0513(5) Uani 1 1 d . . . . .
N17 N 0.78723(17) 0.84777(15) 0.24908(5) 0.0344(5) Uani 1 1 d . . . . .
N46 N 0.4263(2) 0.59375(16) 0.22009(5) 0.0383(5) Uani 1 1 d . . . . .
O18 O 0.88862(16) 0.8473(2) 0.24987(5) 0.0618(6) Uani 1 1 d . . . . .
C10 C 0.56489(17) 0.83557(15) 0.39149(5) 0.0220(4) Uani 1 1 d . . . . .
C37 C 0.41190(17) 0.52378(16) 0.43094(5) 0.0234(5) Uani 1 1 d . . . . .
C21 C 0.64097(17) 0.70211(16) 0.42636(5) 0.0230(5) Uani 1 1 d . . . . .
C49 C 0.41403(17) 0.44538(15) 0.36890(5) 0.0219(4) Uani 1 1 d . . . . .
C38 C 0.37272(17) 0.58275(16) 0.40581(5) 0.0224(4) Uani 1 1 d . . . . .
C51 C 0.46939(18) 0.42956(16) 0.42413(5) 0.0238(5) Uani 1 1 d . . . . .
C39 C 0.38072(17) 0.55020(16) 0.37440(5) 0.0228(5) Uani 1 1 d . . . . .
C22 C 0.61802(18) 0.73744(16) 0.39578(5) 0.0232(5) Uani 1 1 d . . . . .
C9 C 0.51631(17) 0.88172(16) 0.41816(5) 0.0233(5) Uani 1 1 d . . . . .
C1 C 0.55437(18) 0.88430(16) 0.36299(5) 0.0236(5) Uani 1 1 d . . . . .
C8 C 0.53496(18) 0.84406(16) 0.44862(5) 0.0239(5) Uani 1 1 d . . . . .
C50 C 0.46596(17) 0.39165(16) 0.39342(5) 0.0233(5) Uani 1 1 d . . . . .
C12 C 0.73166(18) 0.85980(16) 0.33353(5) 0.0245(5) Uani 1 1 d . . . . .
H12 H 0.771450 0.863114 0.352455 0.029 Uiso 1 1 calc R U . . .
C11 C 0.61600(18) 0.86083(15) 0.33408(5) 0.0233(5) Uani 1 1 d . . . . .
C52 C 0.39568(18) 0.39707(16) 0.34111(5) 0.0258(5) Uani 1 1 d . . . . .
H52 H 0.352344 0.428698 0.325653 0.031 Uiso 1 1 calc R U . . .
C36 C 0.39750(18) 0.55742(16) 0.46099(5) 0.0263(5) Uani 1 1 d . . . . .
H36 H 0.422905 0.517594 0.477696 0.032 Uiso 1 1 calc R U . . .
C4 C 0.44746(18) 0.96696(16) 0.41470(5) 0.0255(5) Uani 1 1 d . . . . .
C55 C 0.51226(18) 0.29597(16) 0.38711(5) 0.0264(5) Uani 1 1 d . . . . .
C20 C 0.60635(17) 0.75700(16) 0.45299(5) 0.0239(5) Uani 1 1 d . . . . .
C13 C 0.78881(19) 0.85404(16) 0.30589(5) 0.0281(5) Uani 1 1 d . . . . .
H13 H 0.867252 0.854229 0.305595 0.034 Uiso 1 1 calc R U . . .
C33 C 0.32558(18) 0.67826(16) 0.41263(5) 0.0255(5) Uani 1 1 d . . . . .
C26 C 0.69614(18) 0.60950(16) 0.43054(5) 0.0273(5) Uani 1 1 d . . . . .
C54 C 0.50051(19) 0.25395(16) 0.35728(5) 0.0278(5) Uani 1 1 d . . . . .
H54 H 0.534835 0.192254 0.352587 0.033 Uiso 1 1 calc R U . . .
C14 C 0.72902(19) 0.84800(17) 0.27867(5) 0.0272(5) Uani 1 1 d . . . . .
C31 C 0.31312(18) 0.71247(17) 0.35813(6) 0.0276(5) Uani 1 1 d . . . . .
H31 H 0.295995 0.757329 0.341835 0.033 Uiso 1 1 calc R U . . .
C15 C 0.61471(18) 0.84453(17) 0.27817(5) 0.0272(5) Uani 1 1 d . . . . .
H15 H 0.575698 0.837795 0.259209 0.033 Uiso 1 1 calc R U . . .
C30 C 0.35640(18) 0.61721(16) 0.35072(5) 0.0256(5) Uani 1 1 d . . . . .
C32 C 0.29553(18) 0.74117(16) 0.38789(5) 0.0272(5) Uani 1 1 d . . . . .
H32 H 0.262815 0.803960 0.392062 0.033 Uiso 1 1 calc R U . . .
C34 C 0.31201(18) 0.70840(17) 0.44363(5) 0.0277(5) Uani 1 1 d . . . . .
H34 H 0.278662 0.770718 0.448079 0.033 Uiso 1 1 calc R U . . .
C23 C 0.64241(19) 0.67523(16) 0.37118(5) 0.0270(5) Uani 1 1 d . . . . .
H23 H 0.622857 0.695421 0.350831 0.032 Uiso 1 1 calc R U . . .
C24 C 0.6952(2) 0.58308(17) 0.37536(6) 0.0299(5) Uani 1 1 d . . . . .
H24 H 0.711812 0.542846 0.357898 0.036 Uiso 1 1 calc R U . . .
C53 C 0.43982(19) 0.30202(17) 0.33522(5) 0.0272(5) Uani 1 1 d . . . . .
H53 H 0.427297 0.271124 0.315759 0.033 Uiso 1 1 calc R U . . .
C6 C 0.41322(19) 0.97149(17) 0.46952(5) 0.0292(5) Uani 1 1 d . . . . .
H6 H 0.377839 1.000437 0.486949 0.035 Uiso 1 1 calc R U . . .
C7 C 0.48164(19) 0.88909(17) 0.47338(5) 0.0280(5) Uani 1 1 d . . . . .
H7 H 0.492138 0.862918 0.493592 0.034 Uiso 1 1 calc R U . . .
C40 C 0.37458(19) 0.60121(16) 0.31696(5) 0.0278(5) Uani 1 1 d . . . . .
C29 C 0.63728(19) 0.72332(18) 0.48200(5) 0.0292(5) Uani 1 1 d . . . . .
H29 H 0.617984 0.761347 0.499723 0.035 Uiso 1 1 calc R U . . .
C41 C 0.47940(19) 0.57955(16) 0.30485(6) 0.0280(5) Uani 1 1 d . . . . .
H41 H 0.539254 0.567366 0.318546 0.034 Uiso 1 1 calc R U . . .
C16 C 0.55870(19) 0.85115(17) 0.30614(5) 0.0275(5) Uani 1 1 d . . . . .
H16 H 0.480278 0.849083 0.306294 0.033 Uiso 1 1 calc R U . . .
C35 C 0.34643(19) 0.64870(17) 0.46738(6) 0.0294(5) Uani 1 1 d . . . . .
H35 H 0.335734 0.669106 0.488219 0.035 Uiso 1 1 calc R U . . .
C5 C 0.39699(19) 1.01058(17) 0.44079(6) 0.0289(5) Uani 1 1 d . . . . .
H5 H 0.351422 1.067529 0.438325 0.035 Uiso 1 1 calc R U . . .
C27 C 0.7238(2) 0.57754(17) 0.46071(6) 0.0310(5) Uani 1 1 d . . . . .
H27 H 0.761494 0.516306 0.463597 0.037 Uiso 1 1 calc R U . . .
C3 C 0.43053(19) 1.00741(17) 0.38494(5) 0.0288(5) Uani 1 1 d . . . . .
H3 H 0.381488 1.061833 0.382198 0.035 Uiso 1 1 calc R U . . .
C25 C 0.7229(2) 0.55094(17) 0.40436(6) 0.0301(5) Uani 1 1 d . . . . .
H25 H 0.760115 0.489314 0.406946 0.036 Uiso 1 1 calc R U . . .
C56 C 0.5670(2) 0.24411(17) 0.41106(6) 0.0313(5) Uani 1 1 d . . . . .
H56 H 0.599362 0.181188 0.406910 0.038 Uiso 1 1 calc R U . . .
C2 C 0.48477(19) 0.96812(17) 0.36015(5) 0.0282(5) Uani 1 1 d . . . . .
H2 H 0.475515 0.997971 0.340393 0.034 Uiso 1 1 calc R U . . .
C42 C 0.4966(2) 0.57573(17) 0.27343(6) 0.0317(5) Uani 1 1 d . . . . .
H42 H 0.567966 0.562320 0.265319 0.038 Uiso 1 1 calc R U . . .
C44 C 0.3029(2) 0.60997(19) 0.26482(6) 0.0337(5) Uani 1 1 d . . . . .
H44 H 0.242705 0.618232 0.250963 0.040 Uiso 1 1 calc R U . . .
C58 C 0.5240(2) 0.37539(18) 0.44676(6) 0.0316(5) Uani 1 1 d . . . . .
H58 H 0.527824 0.401075 0.467213 0.038 Uiso 1 1 calc R U . . .
C45 C 0.2869(2) 0.61596(18) 0.29642(6) 0.0330(5) Uani 1 1 d . . . . .
H45 H 0.215426 0.630286 0.304299 0.040 Uiso 1 1 calc R U . . .
C43 C 0.4076(2) 0.59185(17) 0.25373(6) 0.0331(5) Uani 1 1 d . . . . .
C28 C 0.6962(2) 0.63476(18) 0.48589(6) 0.0314(5) Uani 1 1 d . . . . .
H28 H 0.717312 0.614060 0.506068 0.038 Uiso 1 1 calc R U . . .
C57 C 0.5737(2) 0.28368(18) 0.44018(6) 0.0352(6) Uani 1 1 d . . . . .
H57 H 0.612161 0.248870 0.455987 0.042 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
O19 N17 1.217(3) . ?
O48 N46 1.217(3) . ?
O47 N46 1.231(3) . ?
N17 O18 1.228(3) . ?
N17 C14 1.460(3) . ?
N46 C43 1.471(3) . ?
C10 C22 1.480(3) . ?
C10 C9 1.435(3) . ?
C10 C1 1.401(3) . ?
C37 C38 1.426(3) . ?
C37 C51 1.475(3) . ?
C37 C36 1.386(3) . ?
C21 C22 1.432(3) . ?
C21 C20 1.430(3) . ?
C21 C26 1.425(3) . ?
C49 C39 1.486(3) . ?
C49 C50 1.428(3) . ?
C49 C52 1.383(3) . ?
C38 C39 1.429(3) . ?
C38 C33 1.436(3) . ?
C51 C50 1.422(3) . ?
C51 C58 1.387(3) . ?
C39 C30 1.395(3) . ?
C22 C23 1.385(3) . ?
C9 C8 1.428(3) . ?
C9 C4 1.425(3) . ?
C1 C11 1.489(3) . ?
C1 C2 1.413(3) . ?
C8 C20 1.468(3) . ?
C8 C7 1.389(3) . ?
C50 C55 1.430(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.401(3) . ?
C12 C13 1.382(3) . ?
C11 C16 1.398(3) . ?
C52 H52 0.9500 . ?
C52 C53 1.409(3) . ?
C36 H36 0.9500 . ?
C36 C35 1.402(3) . ?
C4 C5 1.410(3) . ?
C4 C3 1.411(3) . ?
C55 C54 1.414(3) . ?
C55 C56 1.413(3) . ?
C20 C29 1.385(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(3) . ?
C33 C32 1.411(3) . ?
C33 C34 1.409(3) . ?
C26 C27 1.413(3) . ?
C26 C25 1.416(3) . ?
C54 H54 0.9500 . ?
C54 C53 1.366(3) . ?
C14 C15 1.385(3) . ?
C31 H31 0.9500 . ?
C31 C30 1.421(3) . ?
C31 C32 1.360(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(3) . ?
C30 C40 1.491(3) . ?
C32 H32 0.9500 . ?
C34 H34 0.9500 . ?
C34 C35 1.368(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.406(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.367(3) . ?
C53 H53 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.394(3) . ?
C6 C5 1.362(3) . ?
C7 H7 0.9500 . ?
C40 C41 1.403(3) . ?
C40 C45 1.397(3) . ?
C29 H29 0.9500 . ?
C29 C28 1.399(3) . ?
C41 H41 0.9500 . ?
C41 C42 1.374(3) . ?
C16 H16 0.9500 . ?
C35 H35 0.9500 . ?
C5 H5 0.9500 . ?
C27 H27 0.9500 . ?
C27 C28 1.374(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.363(3) . ?
C25 H25 0.9500 . ?
C56 H56 0.9500 . ?
C56 C57 1.369(4) . ?
C2 H2 0.9500 . ?
C42 H42 0.9500 . ?
C42 C43 1.390(4) . ?
C44 H44 0.9500 . ?
C44 C45 1.382(3) . ?
C44 C43 1.376(4) . ?
C58 H58 0.9500 . ?
C58 C57 1.402(3) . ?
C45 H45 0.9500 . ?
C28 H28 0.9500 . ?
C57 H57 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
O19 N17 O18 122.9(2) . . ?
O19 N17 C14 119.8(2) . . ?
O18 N17 C14 117.3(2) . . ?
O48 N46 O47 124.1(2) . . ?
O48 N46 C43 117.8(2) . . ?
O47 N46 C43 118.1(2) . . ?
C9 C10 C22 117.62(19) . . ?
C1 C10 C22 124.5(2) . . ?
C1 C10 C9 117.79(19) . . ?
C38 C37 C51 118.9(2) . . ?
C36 C37 C38 119.3(2) . . ?
C36 C37 C51 121.8(2) . . ?
C20 C21 C22 121.0(2) . . ?
C26 C21 C22 119.9(2) . . ?
C26 C21 C20 119.1(2) . . ?
C50 C49 C39 118.75(19) . . ?
C52 C49 C39 122.8(2) . . ?
C52 C49 C50 118.5(2) . . ?
C37 C38 C39 122.0(2) . . ?
C37 C38 C33 118.3(2) . . ?
C39 C38 C33 119.7(2) . . ?
C50 C51 C37 118.69(19) . . ?
C58 C51 C37 122.4(2) . . ?
C58 C51 C50 118.9(2) . . ?
C38 C39 C49 117.45(19) . . ?
C30 C39 C49 123.6(2) . . ?
C30 C39 C38 119.0(2) . . ?
C21 C22 C10 119.74(19) . . ?
C23 C22 C10 122.4(2) . . ?
C23 C22 C21 117.8(2) . . ?
C8 C9 C10 121.4(2) . . ?
C4 C9 C10 120.2(2) . . ?
C4 C9 C8 118.3(2) . . ?
C10 C1 C11 126.35(19) . . ?
C10 C1 C2 120.2(2) . . ?
C2 C1 C11 113.30(19) . . ?
C9 C8 C20 119.6(2) . . ?
C7 C8 C9 118.8(2) . . ?
C7 C8 C20 121.5(2) . . ?
C49 C50 C55 119.1(2) . . ?
C51 C50 C49 121.57(19) . . ?
C51 C50 C55 119.3(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C13 C12 C11 121.0(2) . . ?
C12 C11 C1 121.2(2) . . ?
C16 C11 C1 119.7(2) . . ?
C16 C11 C12 118.7(2) . . ?
C49 C52 H52 119.3 . . ?
C49 C52 C53 121.5(2) . . ?
C53 C52 H52 119.3 . . ?
C37 C36 H36 119.1 . . ?
C37 C36 C35 121.7(2) . . ?
C35 C36 H36 119.1 . . ?
C5 C4 C9 120.3(2) . . ?
C5 C4 C3 120.3(2) . . ?
C3 C4 C9 119.4(2) . . ?
C54 C55 C50 119.6(2) . . ?
C56 C55 C50 119.2(2) . . ?
C56 C55 C54 121.1(2) . . ?
C21 C20 C8 118.8(2) . . ?
C29 C20 C21 118.7(2) . . ?
C29 C20 C8 122.5(2) . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C14 118.4(2) . . ?
C14 C13 H13 120.8 . . ?
C32 C33 C38 118.9(2) . . ?
C34 C33 C38 119.9(2) . . ?
C34 C33 C32 121.2(2) . . ?
C27 C26 C21 119.6(2) . . ?
C27 C26 C25 120.9(2) . . ?
C25 C26 C21 119.5(2) . . ?
C55 C54 H54 120.0 . . ?
C53 C54 C55 120.0(2) . . ?
C53 C54 H54 120.0 . . ?
C13 C14 N17 119.5(2) . . ?
C13 C14 C15 122.6(2) . . ?
C15 C14 N17 118.0(2) . . ?
C30 C31 H31 119.1 . . ?
C32 C31 H31 119.1 . . ?
C32 C31 C30 121.8(2) . . ?
C14 C15 H15 120.9 . . ?
C14 C15 C16 118.2(2) . . ?
C16 C15 H15 120.9 . . ?
C39 C30 C31 119.7(2) . . ?
C39 C30 C40 126.4(2) . . ?
C31 C30 C40 113.9(2) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 C33 120.4(2) . . ?
C31 C32 H32 119.8 . . ?
C33 C34 H34 119.7 . . ?
C35 C34 C33 120.6(2) . . ?
C35 C34 H34 119.7 . . ?
C22 C23 H23 119.0 . . ?
C22 C23 C24 122.1(2) . . ?
C24 C23 H23 119.0 . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.5(2) . . ?
C25 C24 H24 119.7 . . ?
C52 C53 H53 119.8 . . ?
C54 C53 C52 120.5(2) . . ?
C54 C53 H53 119.8 . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.1(2) . . ?
C8 C7 C6 122.1(2) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C41 C40 C30 121.9(2) . . ?
C45 C40 C30 119.2(2) . . ?
C45 C40 C41 118.7(2) . . ?
C20 C29 H29 119.1 . . ?
C20 C29 C28 121.7(2) . . ?
C28 C29 H29 119.1 . . ?
C40 C41 H41 119.6 . . ?
C42 C41 C40 120.9(2) . . ?
C42 C41 H41 119.6 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 121.0(2) . . ?
C15 C16 H16 119.5 . . ?
C36 C35 H35 120.0 . . ?
C34 C35 C36 120.0(2) . . ?
C34 C35 H35 120.0 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.2(2) . . ?
C28 C27 H27 119.9 . . ?
C4 C3 H3 120.1 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 C26 120.0(2) . . ?
C24 C25 H25 120.0 . . ?
C55 C56 H56 119.7 . . ?
C57 C56 C55 120.6(2) . . ?
C57 C56 H56 119.7 . . ?
C1 C2 H2 119.0 . . ?
C3 C2 C1 121.9(2) . . ?
C3 C2 H2 119.0 . . ?
C41 C42 H42 120.6 . . ?
C41 C42 C43 118.8(2) . . ?
C43 C42 H42 120.6 . . ?
C45 C44 H44 120.5 . . ?
C43 C44 H44 120.5 . . ?
C43 C44 C45 118.9(2) . . ?
C51 C58 H58 119.2 . . ?
C51 C58 C57 121.6(2) . . ?
C57 C58 H58 119.2 . . ?
C40 C45 H45 119.6 . . ?
C44 C45 C40 120.8(2) . . ?
C44 C45 H45 119.6 . . ?
C42 C43 N46 119.2(2) . . ?
C44 C43 N46 118.9(2) . . ?
C44 C43 C42 121.9(2) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 C29 120.4(2) . . ?
C27 C28 H28 119.8 . . ?
C56 C57 C58 120.2(2) . . ?
C56 C57 H57 119.9 . . ?
C58 C57 H57 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O19 N17 C14 C13 -176.6(2) . . . . ?
O19 N17 C14 C15 1.9(3) . . . . ?
O48 N46 C43 C42 -7.3(3) . . . . ?
O48 N46 C43 C44 170.2(2) . . . . ?
O47 N46 C43 C42 172.9(2) . . . . ?
O47 N46 C43 C44 -9.6(3) . . . . ?
N17 C14 C15 C16 -175.9(2) . . . . ?
O18 N17 C14 C13 4.1(3) . . . . ?
O18 N17 C14 C15 -177.4(2) . . . . ?
C10 C22 C23 C24 178.5(2) . . . . ?
C10 C9 C8 C20 0.8(3) . . . . ?
C10 C9 C8 C7 -177.1(2) . . . . ?
C10 C9 C4 C5 178.1(2) . . . . ?
C10 C9 C4 C3 -2.1(3) . . . . ?
C10 C1 C11 C12 -55.8(3) . . . . ?
C10 C1 C11 C16 131.9(2) . . . . ?
C10 C1 C2 C3 3.4(3) . . . . ?
C37 C38 C39 C49 10.1(3) . . . . ?
C37 C38 C39 C30 -170.4(2) . . . . ?
C37 C38 C33 C32 174.40(19) . . . . ?
C37 C38 C33 C34 -4.4(3) . . . . ?
C37 C51 C50 C49 3.7(3) . . . . ?
C37 C51 C50 C55 -174.14(19) . . . . ?
C37 C51 C58 C57 176.9(2) . . . . ?
C37 C36 C35 C34 -1.8(3) . . . . ?
C21 C22 C23 C24 -4.5(3) . . . . ?
C21 C20 C29 C28 -3.4(3) . . . . ?
C21 C26 C27 C28 0.9(3) . . . . ?
C21 C26 C25 C24 -0.4(3) . . . . ?
C49 C39 C30 C31 172.81(19) . . . . ?
C49 C39 C30 C40 -9.3(3) . . . . ?
C49 C50 C55 C54 -3.5(3) . . . . ?
C49 C50 C55 C56 177.9(2) . . . . ?
C49 C52 C53 C54 1.4(3) . . . . ?
C38 C37 C51 C50 -11.5(3) . . . . ?
C38 C37 C51 C58 170.3(2) . . . . ?
C38 C37 C36 C35 -0.7(3) . . . . ?
C38 C39 C30 C31 -6.7(3) . . . . ?
C38 C39 C30 C40 171.2(2) . . . . ?
C38 C33 C32 C31 -1.3(3) . . . . ?
C38 C33 C34 C35 2.0(3) . . . . ?
C51 C37 C38 C39 4.4(3) . . . . ?
C51 C37 C38 C33 -174.66(18) . . . . ?
C51 C37 C36 C35 177.6(2) . . . . ?
C51 C50 C55 C54 174.4(2) . . . . ?
C51 C50 C55 C56 -4.2(3) . . . . ?
C51 C58 C57 C56 -1.6(4) . . . . ?
C39 C49 C50 C51 10.9(3) . . . . ?
C39 C49 C50 C55 -171.24(19) . . . . ?
C39 C49 C52 C53 172.2(2) . . . . ?
C39 C38 C33 C32 -4.6(3) . . . . ?
C39 C38 C33 C34 176.6(2) . . . . ?
C39 C30 C40 C41 -57.7(3) . . . . ?
C39 C30 C40 C45 127.5(2) . . . . ?
C22 C10 C9 C8 10.9(3) . . . . ?
C22 C10 C9 C4 -168.92(19) . . . . ?
C22 C10 C1 C11 -16.0(3) . . . . ?
C22 C10 C1 C2 168.0(2) . . . . ?
C22 C21 C20 C8 7.4(3) . . . . ?
C22 C21 C20 C29 -175.5(2) . . . . ?
C22 C21 C26 C27 176.7(2) . . . . ?
C22 C21 C26 C25 -3.1(3) . . . . ?
C22 C23 C24 C25 1.1(4) . . . . ?
C9 C10 C22 C21 -13.6(3) . . . . ?
C9 C10 C22 C23 163.4(2) . . . . ?
C9 C10 C1 C11 167.1(2) . . . . ?
C9 C10 C1 C2 -8.9(3) . . . . ?
C9 C8 C20 C21 -10.1(3) . . . . ?
C9 C8 C20 C29 172.9(2) . . . . ?
C9 C8 C7 C6 -1.9(3) . . . . ?
C9 C4 C5 C6 -0.2(3) . . . . ?
C9 C4 C3 C2 -3.6(3) . . . . ?
C1 C10 C22 C21 169.5(2) . . . . ?
C1 C10 C22 C23 -13.6(3) . . . . ?
C1 C10 C9 C8 -171.91(19) . . . . ?
C1 C10 C9 C4 8.2(3) . . . . ?
C1 C11 C16 C15 170.0(2) . . . . ?
C8 C9 C4 C5 -1.8(3) . . . . ?
C8 C9 C4 C3 178.1(2) . . . . ?
C8 C20 C29 C28 173.6(2) . . . . ?
C50 C49 C39 C38 -17.7(3) . . . . ?
C50 C49 C39 C30 162.8(2) . . . . ?
C50 C49 C52 C53 -8.6(3) . . . . ?
C50 C51 C58 C57 -1.3(3) . . . . ?
C50 C55 C54 C53 -3.8(3) . . . . ?
C50 C55 C56 C57 1.4(3) . . . . ?
C12 C11 C16 C15 -2.5(3) . . . . ?
C12 C13 C14 N17 176.4(2) . . . . ?
C12 C13 C14 C15 -2.0(3) . . . . ?
C11 C1 C2 C3 -173.1(2) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C52 C49 C39 C38 161.5(2) . . . . ?
C52 C49 C39 C30 -18.0(3) . . . . ?
C52 C49 C50 C51 -168.3(2) . . . . ?
C52 C49 C50 C55 9.5(3) . . . . ?
C36 C37 C38 C39 -177.2(2) . . . . ?
C36 C37 C38 C33 3.8(3) . . . . ?
C36 C37 C51 C50 170.1(2) . . . . ?
C36 C37 C51 C58 -8.1(3) . . . . ?
C4 C9 C8 C20 -179.38(19) . . . . ?
C4 C9 C8 C7 2.8(3) . . . . ?
C4 C3 C2 C1 3.0(4) . . . . ?
C55 C54 C53 C52 4.9(3) . . . . ?
C55 C56 C57 C58 1.5(4) . . . . ?
C20 C21 C22 C10 4.5(3) . . . . ?
C20 C21 C22 C23 -172.6(2) . . . . ?
C20 C21 C26 C27 -5.2(3) . . . . ?
C20 C21 C26 C25 175.0(2) . . . . ?
C20 C8 C7 C6 -179.7(2) . . . . ?
C20 C29 C28 C27 -1.0(4) . . . . ?
C13 C12 C11 C1 -169.4(2) . . . . ?
C13 C12 C11 C16 3.0(3) . . . . ?
C13 C14 C15 C16 2.5(4) . . . . ?
C33 C38 C39 C49 -170.91(18) . . . . ?
C33 C38 C39 C30 8.6(3) . . . . ?
C33 C34 C35 C36 1.1(3) . . . . ?
C26 C21 C22 C10 -177.47(19) . . . . ?
C26 C21 C22 C23 5.4(3) . . . . ?
C26 C21 C20 C8 -170.67(19) . . . . ?
C26 C21 C20 C29 6.4(3) . . . . ?
C26 C27 C28 C29 2.2(4) . . . . ?
C54 C55 C56 C57 -177.2(2) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
C31 C30 C40 C41 120.2(2) . . . . ?
C31 C30 C40 C45 -54.5(3) . . . . ?
C30 C31 C32 C33 3.4(3) . . . . ?
C30 C40 C41 C42 -172.9(2) . . . . ?
C30 C40 C45 C44 174.5(2) . . . . ?
C32 C33 C34 C35 -176.8(2) . . . . ?
C32 C31 C30 C39 0.7(3) . . . . ?
C32 C31 C30 C40 -177.4(2) . . . . ?
C34 C33 C32 C31 177.5(2) . . . . ?
C23 C24 C25 C26 1.5(4) . . . . ?
C7 C8 C20 C21 167.6(2) . . . . ?
C7 C8 C20 C29 -9.3(3) . . . . ?
C7 C6 C5 C4 1.2(3) . . . . ?
C40 C41 C42 C43 -1.2(3) . . . . ?
C41 C40 C45 C44 -0.4(4) . . . . ?
C41 C42 C43 N46 176.4(2) . . . . ?
C41 C42 C43 C44 -1.0(4) . . . . ?
C5 C4 C3 C2 176.2(2) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C27 C26 C25 C24 179.8(2) . . . . ?
C3 C4 C5 C6 179.9(2) . . . . ?
C25 C26 C27 C28 -179.3(2) . . . . ?
C56 C55 C54 C53 174.8(2) . . . . ?
C2 C1 C11 C12 120.4(2) . . . . ?
C2 C1 C11 C16 -51.9(3) . . . . ?
C58 C51 C50 C49 -178.0(2) . . . . ?
C58 C51 C50 C55 4.1(3) . . . . ?
C45 C40 C41 C42 1.9(3) . . . . ?
C45 C44 C43 N46 -175.0(2) . . . . ?
C45 C44 C43 C42 2.5(4) . . . . ?
C43 C44 C45 C40 -1.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.469
_oxdiff_exptl_absorpt_empirical_full_min 0.752
_exptl_crystal_preparation       Luminescent
