# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_3301
_database_code_depnum_ccdc_archive 'CCDC 2340392'
loop_
_audit_author_name
_audit_author_address
'Pengyang Jing'
;Hunan Normal University
China
;
_audit_update_record             
;
2024-03-14 deposited with the CCDC.	2024-12-19 downloaded from the CCDC.
;
_audit_creation_date             2023-08-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H21 Cl N2 O3'
_chemical_formula_sum            'C31 H21 Cl N2 O3'
_chemical_formula_weight         504.95
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C100 H100 N1 Cl1 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'
Cl Cl 0.3639 0.7018 '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                   11.7884(3)
_cell_length_b                   17.5725(4)
_cell_length_c                   24.1043(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4993.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    16577
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.3570
_cell_measurement_theta_min      2.4670
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.637
_exptl_absorpt_coefficient_mu    1.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0948
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            66058
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         3.667
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     12.00  96.00   1.00    2.00    --   34.73  77.00 120.00   84
  2  ω    104.00 140.00   1.00    8.00    --  105.88 111.00  90.00   36
  3  ω     88.00 115.00   1.00    8.00    --  105.88 -30.00   0.00   27
  4  ω     41.00  66.00   1.00    8.00    --  105.88 -30.00   0.00   25
  5  ω     41.00 124.00   1.00    8.00    --  105.88 -61.00 -60.00   83
  6  ω     43.00  70.00   1.00    2.00    --   34.73-125.00-180.00   27
  7  ω      8.00  92.00   1.00    2.00    --   34.73  77.00   0.00   84
  8  ω     42.00 120.00   1.00    8.00    --  105.88 -77.00-180.00   78
  9  ω      4.00  39.00   1.00    2.00    --   34.73 -99.00  60.00   35
 10  ω     51.00 107.00   1.00    8.00    --  105.88 -94.00  60.00   56
 11  ω    -88.00  -2.00   1.00    2.00    --  -34.73 125.00-120.00   86
 12  ω     60.00  96.00   1.00    2.00    --   34.73  57.00  90.00   36
 13  ω     42.00  88.00   1.00    2.00    --   34.73-125.00  90.00   46
 14  ω     69.00 102.00   1.00    2.00    --   34.73  77.00-120.00   33
 15  ω    -33.00  26.00   1.00    2.00    --   34.73 -77.00-120.00   59
 16  ω     69.00  96.00   1.00    2.00    --   34.73  77.00 -90.00   27
 17  ω      8.00  68.00   1.00    2.00    --   34.73  77.00-180.00   60
 18  ω    -33.00  44.00   1.00    2.00    --   34.73 -57.00 -30.00   77
 19  ω     16.00  48.00   1.00    2.00    --   34.73  38.00  30.00   32
 20  ω      8.00  54.00   1.00    2.00    --   34.73  77.00-120.00   46
 21  ω     38.00  64.00   1.00    2.00    --   34.73  77.00 -30.00   26
 22  ω    -21.00  50.00   1.00    2.00    --   34.73 -57.00 150.00   71
 23  ω     10.00  36.00   1.00    2.00    --   34.73  77.00 -30.00   26
 24  ω     19.00  47.00   1.00    2.00    --   34.73  57.00  90.00   28
 25  ω     15.00  60.00   1.00    2.00    --   34.73  77.00 -90.00   45
 26  ω    -34.00  34.00   1.00    2.00    --   34.73 -38.00  90.00   68
 27  ω      8.00 106.00   1.00    2.00    --   34.73  19.00 -90.00   98
 28  ω     36.00  61.00   1.00    2.00    --   34.73 -77.00-120.00   25
 29  ω      8.00  53.00   1.00    2.00    --   34.73  77.00  90.00   45
 30  ω     57.00 102.00   1.00    2.00    --   34.73  38.00  30.00   45
 31  ω     77.00 102.00   1.00    2.00    --   34.73  77.00  90.00   25
 32  ω     79.00 104.00   1.00    8.00    --  105.25  77.00-180.00   25
 33  ω     87.00 113.00   1.00    8.00    --  105.25  61.00  30.00   26
 34  ω     79.00 104.00   1.00    8.00    --  105.25  77.00-120.00   25
 35  ω    133.00 172.00   1.00    8.00    --  105.25  77.00  60.00   39
 36  ω     79.00 105.00   1.00    8.00    --  105.25  77.00  60.00   26
 37  ω     79.00 104.00   1.00    8.00    --  105.25  77.00 -30.00   25
 38  ω    123.00 167.00   1.00    8.00    --  105.25  77.00 -30.00   44
 39  ω     36.00  74.00   1.00    8.00    --  105.25 -94.00 120.00   38
 40  ω     87.00 124.00   1.00    8.00    --  105.25  61.00 120.00   37
 41  ω    110.00 172.00   1.00    8.00    --  105.25  77.00 150.00   62
 42  ω     87.00 113.00   1.00    8.00    --  105.25  61.00 -30.00   26
 43  ω    132.00 160.00   1.00    8.00    --  105.25  77.00 120.00   28
 44  ω     79.00 104.00   1.00    8.00    --  105.25  77.00 150.00   25
 45  ω    148.00 173.00   1.00    8.00    --  105.25  77.00  90.00   25
 46  ω     87.00 113.00   1.00    8.00    --  105.25  61.00   0.00   26
 47  ω    122.00 173.00   1.00    8.00    --  105.25  77.00   0.00   51
 48  ω     79.00 104.00   1.00    8.00    --  105.25  77.00  90.00   25
 49  ω     79.00 104.00   1.00    8.00    --  105.25  77.00   0.00   25
 50  ω     87.00 113.00   1.00    8.00    --  105.25  61.00-150.00   26
 51  ω     87.00 112.00   1.00    8.00    --  105.25  61.00 150.00   25
 52  ω    115.00 173.00   1.00    8.00    --  105.25  77.00-150.00   58
 53  ω     79.00 105.00   1.00    8.00    --  105.25  77.00 -90.00   26
 54  ω     87.00 112.00   1.00    8.00    --  105.25  61.00  90.00   25
 55  ω     87.00 113.00   1.00    8.00    --  105.25  61.00 -60.00   26
 56  ω     79.00 104.00   1.00    8.00    --  105.25  77.00 120.00   25
 57  ω     79.00 104.00   1.00    8.00    --  105.25  77.00-150.00   25
 58  ω     87.00 112.00   1.00    8.00    --  105.25  61.00-120.00   25
 59  ω     87.00 113.00   1.00    8.00    --  105.25  61.00-180.00   26
 60  ω    147.00 172.00   1.00    8.00    --  105.25  61.00-180.00   25
 61  ω     87.00 121.00   1.00    8.00    --  105.25  61.00  60.00   34
 62  ω     86.00 112.00   1.00    8.00    --  105.25  30.00 -90.00   26
 63  ω    118.00 152.00   1.00    8.00    --  105.25  30.00 -90.00   34
 64  ω     84.00 109.00   1.00    8.00    --  105.25  30.00  30.00   25
 65  ω     84.00 165.00   1.00    8.00    --  105.25  30.00  60.00   81
 66  ω     85.00 137.00   1.00    8.00    --  105.25  30.00 120.00   52
 67  ω     84.00 118.00   1.00    8.00    --  105.25  30.00-120.00   34
 68  ω     84.00 117.00   1.00    8.00    --  105.25  30.00-180.00   33
 69  ω     87.00 165.00   1.00    8.00    --  105.25  61.00 -90.00   78
 70  ω    147.00 172.00   1.00    8.00    --  105.25  77.00  30.00   25
 71  ω     36.00 114.00   1.00    8.00    --  105.25-111.00-180.00   78
 72  ω     84.00 109.00   1.00    8.00    --  105.25  30.00-150.00   25
 73  ω     79.00 104.00   1.00    8.00    --  105.25  77.00  30.00   25
 74  ω     84.00 110.00   1.00    8.00    --  105.25  30.00   0.00   26
 75  ω    128.00 154.00   1.00    8.00    --  105.25  30.00-150.00   26
 76  ω     53.00 115.00   1.00    8.00    --  105.25-111.00 -30.00   62
 77  ω    129.00 154.00   1.00    8.00    --  105.25  77.00-120.00   25
 78  ω     79.00 170.00   1.00    8.00    --  105.25  77.00 -60.00   91
 79  ω     64.00  90.00   1.00    8.00    --  105.25-111.00  30.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0807823000
_diffrn_orient_matrix_UB_12      -0.0443314000
_diffrn_orient_matrix_UB_13      -0.0384682000
_diffrn_orient_matrix_UB_21      0.0826334000
_diffrn_orient_matrix_UB_22      -0.0678508000
_diffrn_orient_matrix_UB_23      0.0000435000
_diffrn_orient_matrix_UB_31      -0.0609327000
_diffrn_orient_matrix_UB_32      -0.0334620000
_diffrn_orient_matrix_UB_33      0.0510516000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3614
_reflns_number_total             4399
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         1.407
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0819
_refine_ls_restrained_S_all      1.050
_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)+(0.1578P)²+2.3423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2224
_refine_ls_wR_factor_ref         0.2321
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C8(H8), C10(H10), C11(H11), C19(H19), C21(H21),
 C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_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
O1 O 0.8264(3) 0.48551(16) 0.67381(10) 0.0656(7) Uani 1 1 d . . . . .
O2 O 0.9025(2) 0.29305(12) 0.55607(10) 0.0548(6) Uani 1 1 d . . . . .
O3 O 0.9769(2) 0.50900(18) 0.42496(14) 0.0757(9) Uani 1 1 d . . . . .
N1 N 0.8584(2) 0.38640(14) 0.61579(9) 0.0396(6) Uani 1 1 d . . . . .
N2 N 0.7169(2) 0.34512(13) 0.48960(11) 0.0403(6) Uani 1 1 d . . . . .
C1 C 0.6491(3) 0.61130(18) 0.55977(14) 0.0559(9) Uani 1 1 d . . . . .
H1 H 0.614675 0.656866 0.569883 0.067 Uiso 1 1 calc R . . . .
C2 C 0.7081(3) 0.56926(18) 0.59833(13) 0.0521(8) Uani 1 1 d . . . . .
H2 H 0.715784 0.587006 0.634480 0.063 Uiso 1 1 calc R . . . .
C3 C 0.7562(3) 0.50015(15) 0.58299(11) 0.0352(6) Uani 1 1 d . . . . .
C4 C 0.7489(2) 0.47215(14) 0.52911(11) 0.0340(6) Uani 1 1 d . . . . .
C5 C 0.6900(2) 0.51569(15) 0.48938(11) 0.0352(6) Uani 1 1 d . . . . .
C6 C 0.6414(3) 0.58509(17) 0.50592(13) 0.0471(7) Uani 1 1 d . . . . .
H6 H 0.602964 0.614253 0.479790 0.057 Uiso 1 1 calc R . . . .
C7 C 0.6864(2) 0.49943(14) 0.42872(11) 0.0337(6) Uani 1 1 d . . . . .
C8 C 0.5888(3) 0.51189(16) 0.39825(13) 0.0419(7) Uani 1 1 d . . . . .
H8 H 0.520172 0.520585 0.416185 0.050 Uiso 1 1 calc R . . . .
C9 C 0.5938(3) 0.51133(17) 0.34088(13) 0.0460(7) Uani 1 1 d . . . . .
C10 C 0.6937(3) 0.49980(19) 0.31255(13) 0.0502(8) Uani 1 1 d . . . . .
H10 H 0.695753 0.501199 0.273991 0.060 Uiso 1 1 calc R . . . .
C11 C 0.7905(3) 0.48616(19) 0.34283(14) 0.0486(7) Uani 1 1 d . . . . .
H11 H 0.858870 0.478023 0.324532 0.058 Uiso 1 1 calc R . . . .
C12 C 0.7873(2) 0.48441(16) 0.40025(12) 0.0378(6) Uani 1 1 d . . . . .
C13 C 0.8941(2) 0.46997(17) 0.43198(12) 0.0412(7) Uani 1 1 d . . . . .
C14 C 0.8982(2) 0.40048(16) 0.46898(12) 0.0379(6) Uani 1 1 d . . . . .
H14 H 0.973143 0.395850 0.486265 0.046 Uiso 1 1 calc R . . . .
C15 C 0.8023(2) 0.39649(15) 0.51449(11) 0.0324(6) Uani 1 1 d . . . . .
C16 C 0.8587(2) 0.35451(15) 0.56403(12) 0.0377(6) Uani 1 1 d . . . . .
C17 C 0.8164(3) 0.45862(17) 0.62794(12) 0.0432(7) Uani 1 1 d . . . . .
C18 C 0.9198(3) 0.3451(2) 0.65993(13) 0.0501(8) Uani 1 1 d . . . . .
H18A H 0.949122 0.381496 0.686567 0.060 Uiso 1 1 calc R . . . .
H18B H 0.983774 0.318491 0.643727 0.060 Uiso 1 1 calc R . . . .
C19 C 0.7388(4) 0.3079(3) 0.7077(3) 0.108(2) Uani 1 1 d . . . . .
H19 H 0.712114 0.356844 0.701003 0.129 Uiso 1 1 calc R . . . .
C20 C 0.8449(3) 0.28845(19) 0.68973(13) 0.0498(8) Uani 1 1 d . . . . .
C21 C 0.8839(4) 0.2168(2) 0.70220(15) 0.0595(9) Uani 1 1 d . . . . .
H21 H 0.955941 0.201880 0.690894 0.071 Uiso 1 1 calc R . . . .
C22 C 0.8156(5) 0.1664(2) 0.73172(17) 0.0745(12) Uani 1 1 d . . . . .
H22 H 0.843294 0.118361 0.740483 0.089 Uiso 1 1 calc R . . . .
C23 C 0.6704(5) 0.2572(4) 0.7354(3) 0.129(3) Uani 1 1 d . . . . .
H23 H 0.597342 0.271442 0.745608 0.155 Uiso 1 1 calc R . . . .
C24 C 0.7092(5) 0.1861(3) 0.7480(2) 0.0899(15) Uani 1 1 d . . . . .
H24 H 0.663839 0.151869 0.767272 0.108 Uiso 1 1 calc R . . . .
C25 C 0.8727(3) 0.33042(17) 0.43379(12) 0.0463(7) Uani 1 1 d . . . . .
C26 C 0.9365(4) 0.2976(2) 0.39204(15) 0.0669(11) Uani 1 1 d . . . . .
H26 H 1.006293 0.317734 0.381703 0.080 Uiso 1 1 calc R . . . .
C27 C 0.8921(6) 0.2330(3) 0.36584(17) 0.0866(16) Uani 1 1 d . . . . .
H27 H 0.933402 0.209328 0.337860 0.104 Uiso 1 1 calc R . . . .
C28 C 0.7873(5) 0.2038(2) 0.3811(2) 0.0845(15) Uani 1 1 d . . . . .
H28 H 0.759570 0.160760 0.363272 0.101 Uiso 1 1 calc R . . . .
C29 C 0.7235(4) 0.2373(2) 0.42217(17) 0.0659(10) Uani 1 1 d . . . . .
H29 H 0.653077 0.217923 0.432216 0.079 Uiso 1 1 calc R . . . .
C30 C 0.7684(3) 0.30144(16) 0.44816(13) 0.0443(7) Uani 1 1 d . . . . .
C31 C 0.6336(3) 0.3110(2) 0.52635(18) 0.0589(9) Uani 1 1 d . . . . .
H31A H 0.669089 0.271725 0.547949 0.088 Uiso 1 1 calc GR . . . .
H31B H 0.573255 0.289369 0.504731 0.088 Uiso 1 1 calc GR . . . .
H31C H 0.603426 0.349215 0.550651 0.088 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.47030(9) 0.53026(7) 0.30308(4) 0.0751(4) Uani 1 1 d . . . A 1


_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
O1 C17 1.208(4) . ?
O2 C16 1.213(4) . ?
O3 C13 1.205(4) . ?
N1 C16 1.368(4) . ?
N1 C17 1.393(4) . ?
N1 C18 1.477(4) . ?
N2 C15 1.480(3) . ?
N2 C30 1.399(4) . ?
N2 C31 1.452(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.376(5) . ?
C1 C6 1.380(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(4) . ?
C3 C4 1.391(4) . ?
C3 C17 1.487(4) . ?
C4 C5 1.409(4) . ?
C4 C15 1.513(4) . ?
C5 C6 1.405(4) . ?
C5 C7 1.490(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(4) . ?
C7 C12 1.399(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.384(5) . ?
C9 C10 1.376(5) . ?
C9 Cl1 1.750(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(5) . ?
C12 C13 1.494(4) . ?
C13 C14 1.513(4) . ?
C14 H14 0.9800 . ?
C14 C15 1.577(4) . ?
C14 C25 1.525(4) . ?
C15 C16 1.553(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C20 1.512(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.367(6) . ?
C19 C23 1.374(7) . ?
C20 C21 1.374(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.392(6) . ?
C22 H22 0.9300 . ?
C22 C24 1.358(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.365(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.382(5) . ?
C25 C30 1.376(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.401(7) . ?
C27 H27 0.9300 . ?
C27 C28 1.388(8) . ?
C28 H28 0.9300 . ?
C28 C29 1.374(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.393(5) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?

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
C16 N1 C17 124.4(2) . . ?
C16 N1 C18 117.1(3) . . ?
C17 N1 C18 118.0(3) . . ?
C30 N2 C15 109.2(2) . . ?
C30 N2 C31 120.2(3) . . ?
C31 N2 C15 117.7(3) . . ?
C2 C1 H1 120.4 . . ?
C2 C1 C6 119.3(3) . . ?
C6 C1 H1 120.4 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.7(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 122.1(3) . . ?
C2 C3 C17 115.4(3) . . ?
C4 C3 C17 122.4(3) . . ?
C3 C4 C5 118.2(2) . . ?
C3 C4 C15 120.2(2) . . ?
C5 C4 C15 121.6(2) . . ?
C4 C5 C7 125.3(2) . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 C7 115.7(3) . . ?
C1 C6 C5 122.0(3) . . ?
C1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C8 C7 C5 121.0(3) . . ?
C8 C7 C12 118.5(3) . . ?
C12 C7 C5 119.6(3) . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 Cl1 118.9(3) . . ?
C10 C9 C8 122.2(3) . . ?
C10 C9 Cl1 118.8(2) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.2(3) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 C13 119.8(3) . . ?
C11 C12 C7 120.6(3) . . ?
C11 C12 C13 119.5(3) . . ?
O3 C13 C12 120.9(3) . . ?
O3 C13 C14 121.1(3) . . ?
C12 C13 C14 117.8(2) . . ?
C13 C14 H14 110.3 . . ?
C13 C14 C15 115.0(2) . . ?
C13 C14 C25 108.5(2) . . ?
C15 C14 H14 110.3 . . ?
C25 C14 H14 110.3 . . ?
C25 C14 C15 102.1(2) . . ?
N2 C15 C4 110.3(2) . . ?
N2 C15 C14 103.5(2) . . ?
N2 C15 C16 108.3(2) . . ?
C4 C15 C14 114.9(2) . . ?
C4 C15 C16 114.6(2) . . ?
C16 C15 C14 104.4(2) . . ?
O2 C16 N1 120.7(3) . . ?
O2 C16 C15 118.9(3) . . ?
N1 C16 C15 120.4(2) . . ?
O1 C17 N1 120.9(3) . . ?
O1 C17 C3 121.4(3) . . ?
N1 C17 C3 117.6(3) . . ?
N1 C18 H18A 109.1 . . ?
N1 C18 H18B 109.1 . . ?
N1 C18 C20 112.3(3) . . ?
H18A C18 H18B 107.9 . . ?
C20 C18 H18A 109.1 . . ?
C20 C18 H18B 109.1 . . ?
C20 C19 H19 119.0 . . ?
C20 C19 C23 121.9(5) . . ?
C23 C19 H19 119.0 . . ?
C19 C20 C18 121.3(3) . . ?
C19 C20 C21 117.7(4) . . ?
C21 C20 C18 120.8(3) . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.1(4) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 119.4 . . ?
C24 C22 C21 121.3(4) . . ?
C24 C22 H22 119.4 . . ?
C19 C23 H23 119.9 . . ?
C24 C23 C19 120.3(5) . . ?
C24 C23 H23 119.9 . . ?
C22 C24 C23 118.6(4) . . ?
C22 C24 H24 120.7 . . ?
C23 C24 H24 120.7 . . ?
C26 C25 C14 129.4(3) . . ?
C30 C25 C14 109.6(2) . . ?
C30 C25 C26 121.0(3) . . ?
C25 C26 H26 121.2 . . ?
C25 C26 C27 117.6(4) . . ?
C27 C26 H26 121.2 . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.8(4) . . ?
C28 C27 H27 119.6 . . ?
C27 C28 H28 119.3 . . ?
C29 C28 C27 121.3(4) . . ?
C29 C28 H28 119.3 . . ?
C28 C29 H29 121.2 . . ?
C28 C29 C30 117.5(5) . . ?
C30 C29 H29 121.2 . . ?
C25 C30 N2 111.4(3) . . ?
C25 C30 C29 121.7(3) . . ?
C29 C30 N2 126.9(3) . . ?
N2 C31 H31A 109.5 . . ?
N2 C31 H31B 109.5 . . ?
N2 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.004
_oxdiff_exptl_absorpt_empirical_full_min 0.498
####################################################################### 
# 
# 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_2521
_database_code_depnum_ccdc_archive 'CCDC 2359843'
loop_
_audit_author_name
_audit_author_address
'Jing Pengyang'
;University
China
;
_audit_update_record             
;
2024-06-01 deposited with the CCDC.	2024-12-19 downloaded from the CCDC.
;
_audit_creation_date             2022-09-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H20 N2 O2'
_chemical_formula_sum            'C31 H20 N2 O2'
_chemical_formula_weight         452.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   23.3443(12)
_cell_length_b                   9.3993(3)
_cell_length_c                   23.0066(11)
_cell_angle_alpha                90
_cell_angle_beta                 117.957(7)
_cell_angle_gamma                90
_cell_volume                     4459.0(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3146
_cell_measurement_temperature    293(10)
_cell_measurement_theta_max      69.5070
_cell_measurement_theta_min      3.8320
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.823
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16302
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.598
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         2.143
_diffrn_ambient_temperature      293(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  27.00   1.00    2.00    --  -34.73  57.00  30.00   26
  2  ω      5.00  46.00   1.00    2.00    --   34.73  19.00 -90.00   41
  3  ω     56.00 105.00   1.00    2.00    --   34.73  19.00 -90.00   49
  4  ω    101.00 171.00   1.00    8.00    --  105.25  45.00  30.00   70
  5  ω    140.00 166.00   1.00    8.00    --  105.25 111.00 -30.00   26
  6  ω    109.00 174.00   1.00    8.00    --  105.25 111.00 -60.00   65
  7  ω     84.00 175.00   1.00    8.00    --  105.25  30.00 -60.00   91
  8  ω     87.00 112.00   1.00    8.00    --  105.25-111.00 150.00   25
  9  ω     44.00 123.00   1.00    8.00    --  105.25 -61.00   0.00   79
 10  ω     50.00 104.00   1.00    8.00    --  105.25 -94.00-120.00   54
 11  ω     38.00  64.00   1.00    2.00    --   34.73-125.00-150.00   26
 12  ω     25.00  82.00   1.00    2.00    --   34.73-125.00   0.00   57
 13  ω    -26.00  63.00   1.00    2.00    --   34.73 -19.00  60.00   89
 14  ω    -51.00 -15.00   1.00    2.00    --  -34.73  57.00 -90.00   36
 15  ω    -49.00 -23.00   1.00    2.00    --  -34.73  57.00  30.00   26
 16  ω     57.00 141.00   1.00    8.00    --  105.25 178.00  60.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0703709000
_diffrn_orient_matrix_UB_12      0.0364245000
_diffrn_orient_matrix_UB_13      0.0163643000
_diffrn_orient_matrix_UB_21      -0.0239453000
_diffrn_orient_matrix_UB_22      0.1356366000
_diffrn_orient_matrix_UB_23      -0.0422453000
_diffrn_orient_matrix_UB_31      0.0081755000
_diffrn_orient_matrix_UB_32      0.0845288000
_diffrn_orient_matrix_UB_33      0.0607214000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5164
_reflns_number_total             7877
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.163
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     633
_refine_ls_number_reflns         7877
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      1.027
_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)+(0.0672P)²+0.0293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1619
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18), C00V(H00V)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C28(H28), C29(H29), C30(H30),
  C32(H32), C33(H33), C34(H34), C35(H35), C38(H38), C41(H41), C42(H42),
 C43(H43), C51(H51), C52(H52), C53(H53), C54(H54), C56(H56), C57(H57), C58(H58),
  C59(H59)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C48(H48A,H48B,H48C)
;
_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
O1 O 0.54403(13) 0.6936(2) 0.37496(16) 0.0937(8) Uani 1 1 d . . . . .
O2 O 0.75464(12) 0.4249(3) 0.48810(11) 0.0912(8) Uani 1 1 d . . . . .
N1 N 0.56618(11) 0.4540(2) 0.30779(11) 0.0558(5) Uani 1 1 d . . . . .
N2 N 0.48851(11) 0.5271(2) 0.39817(11) 0.0551(5) Uani 1 1 d . . . . .
C1 C 0.37114(17) 0.8107(4) 0.38445(18) 0.0841(10) Uani 1 1 d . . . . .
H1 H 0.359744 0.905295 0.373107 0.101 Uiso 1 1 calc R . . . .
C2 C 0.33537(17) 0.7277(5) 0.40579(19) 0.0848(10) Uani 1 1 d . . . . .
H2 H 0.300005 0.767770 0.407972 0.102 Uiso 1 1 calc R . . . .
C3 C 0.35082(16) 0.5885(4) 0.42368(17) 0.0787(10) Uani 1 1 d . . . . .
H3 H 0.326726 0.534691 0.438375 0.094 Uiso 1 1 calc R . . . .
C4 C 0.40365(13) 0.5288(4) 0.41941(14) 0.0619(7) Uani 1 1 d . . . . .
C5 C 0.43926(13) 0.6135(3) 0.39795(13) 0.0593(7) Uani 1 1 d . . . . .
C6 C 0.42356(16) 0.7537(4) 0.37992(16) 0.0716(8) Uani 1 1 d . . . . .
H6 H 0.447420 0.808242 0.365187 0.086 Uiso 1 1 calc R . . . .
C7 C 0.43244(14) 0.3906(3) 0.43299(14) 0.0630(7) Uani 1 1 d . . . . .
H7 H 0.418621 0.313346 0.448444 0.076 Uiso 1 1 calc R . . . .
C8 C 0.48331(13) 0.3903(3) 0.41965(13) 0.0544(6) Uani 1 1 d . . . . .
C9 C 0.52809(13) 0.2798(3) 0.42195(13) 0.0548(6) Uani 1 1 d . . . . .
C10 C 0.52279(16) 0.1430(3) 0.44350(15) 0.0658(8) Uani 1 1 d . . . . .
H10 H 0.493024 0.126082 0.458911 0.079 Uiso 1 1 calc R . . . .
C11 C 0.56071(17) 0.0353(3) 0.44202(17) 0.0747(9) Uani 1 1 d . . . . .
H11 H 0.557980 -0.053812 0.458110 0.090 Uiso 1 1 calc R . . . .
C12 C 0.60362(16) 0.0568(3) 0.41670(16) 0.0688(8) Uani 1 1 d . . . . .
H12 H 0.628076 -0.018930 0.414316 0.083 Uiso 1 1 calc R . . . .
C13 C 0.61027(14) 0.1914(3) 0.39480(14) 0.0557(6) Uani 1 1 d . . . . .
C14 C 0.57380(13) 0.3051(3) 0.39982(12) 0.0508(6) Uani 1 1 d . . . . .
C15 C 0.58078(13) 0.4550(3) 0.37756(13) 0.0499(6) Uani 1 1 d . . . . .
C16 C 0.50670(18) 0.4004(5) 0.25789(16) 0.0942(12) Uani 1 1 d . . . . .
H16A H 0.479631 0.478087 0.233017 0.141 Uiso 1 1 calc GR . . . .
H16B H 0.485181 0.347247 0.277621 0.141 Uiso 1 1 calc GR . . . .
H16C H 0.514981 0.339339 0.229192 0.141 Uiso 1 1 calc GR . . . .
C17 C 0.53696(15) 0.5697(3) 0.38398(15) 0.0616(7) Uani 1 1 d . . . . .
C18 C 0.65097(13) 0.5199(3) 0.41263(13) 0.0528(6) Uani 1 1 d . . . . .
H18 H 0.656199 0.584354 0.448259 0.063 Uiso 1 1 calc R . . . .
C19 C 0.65386(13) 0.6005(3) 0.35678(14) 0.0524(6) Uani 1 1 d . . . . .
C20 C 0.60401(13) 0.5543(3) 0.29773(14) 0.0527(6) Uani 1 1 d . . . . .
C21 C 0.59844(17) 0.6041(3) 0.23833(16) 0.0693(8) Uani 1 1 d . . . . .
H21 H 0.564816 0.574373 0.198292 0.083 Uiso 1 1 calc R . . . .
C22 C 0.64458(19) 0.6992(4) 0.2410(2) 0.0817(10) Uani 1 1 d . . . . .
H22 H 0.641780 0.733856 0.201922 0.098 Uiso 1 1 calc R . . . .
C23 C 0.69423(19) 0.7440(4) 0.2993(2) 0.0851(11) Uani 1 1 d . . . . .
H23 H 0.724784 0.807796 0.299511 0.102 Uiso 1 1 calc R . . . .
C24 C 0.69912(16) 0.6944(3) 0.35822(18) 0.0720(9) Uani 1 1 d . . . . .
H24 H 0.732759 0.724593 0.398150 0.086 Uiso 1 1 calc R . . . .
C25 C 0.70652(14) 0.4150(3) 0.43560(13) 0.0585(7) Uani 1 1 d . . . . .
C26 C 0.70246(13) 0.3091(3) 0.38550(13) 0.0550(6) Uani 1 1 d . . . . .
C27 C 0.74358(15) 0.3196(3) 0.35731(16) 0.0661(8) Uani 1 1 d . . . . .
H27 H 0.775536 0.389348 0.371654 0.079 Uiso 1 1 calc R . . . .
C28 C 0.73709(18) 0.2269(3) 0.30826(18) 0.0759(9) Uani 1 1 d . . . . .
H28 H 0.764040 0.235106 0.288834 0.091 Uiso 1 1 calc R . . . .
C29 C 0.69061(18) 0.1224(4) 0.28814(17) 0.0759(9) Uani 1 1 d . . . . .
H29 H 0.685626 0.060475 0.254560 0.091 Uiso 1 1 calc R . . . .
C30 C 0.65151(16) 0.1092(3) 0.31752(16) 0.0698(8) Uani 1 1 d . . . . .
H30 H 0.622150 0.034212 0.305275 0.084 Uiso 1 1 calc R . . . .
C31 C 0.65452(13) 0.2047(3) 0.36512(13) 0.0544(6) Uani 1 1 d . . . . .
O3 O 0.70577(11) 0.7274(3) 0.56649(14) 0.0937(8) Uani 1 1 d . . . . .
O4 O 0.93043(14) 0.4704(3) 0.63573(11) 0.0914(8) Uani 1 1 d . . . . .
N3 N 0.91797(11) 0.7443(3) 0.67462(10) 0.0538(5) Uani 1 1 d . . . . .
N4 N 0.90137(11) 0.5471(3) 0.53285(10) 0.0553(6) Uani 1 1 d . . . . .
C00V C 0.81429(14) 0.6361(3) 0.61476(13) 0.0544(6) Uani 1 1 d . . . . .
H00V H 0.795628 0.550985 0.587820 0.065 Uiso 1 1 calc R . . . .
C011 C 0.76328(14) 0.7490(3) 0.60204(15) 0.0625(7) Uani 1 1 d . . . . .
C32 C 0.92983(17) 0.3717(5) 0.41098(16) 0.0817(11) Uani 1 1 d . . . . .
H32 H 0.924681 0.394910 0.369511 0.098 Uiso 1 1 calc R . . . .
C33 C 0.95375(18) 0.2423(5) 0.43825(19) 0.0876(12) Uani 1 1 d . . . . .
H33 H 0.965380 0.177352 0.415106 0.105 Uiso 1 1 calc R . . . .
C34 C 0.96108(17) 0.2054(4) 0.49921(18) 0.0851(11) Uani 1 1 d . . . . .
H34 H 0.977168 0.115873 0.516222 0.102 Uiso 1 1 calc R . . . .
C35 C 0.94497(16) 0.2992(4) 0.53588(16) 0.0715(8) Uani 1 1 d . . . . .
H35 H 0.949860 0.274401 0.577089 0.086 Uiso 1 1 calc R . . . .
C36 C 0.92161(13) 0.4295(3) 0.50881(13) 0.0584(7) Uani 1 1 d . . . . .
C37 C 0.91319(14) 0.4687(4) 0.44659(14) 0.0676(8) Uani 1 1 d . . . . .
C38 C 0.88784(16) 0.6087(4) 0.43356(14) 0.0703(9) Uani 1 1 d . . . . .
H38 H 0.877266 0.660169 0.395320 0.084 Uiso 1 1 calc R . . . .
C39 C 0.88153(13) 0.6554(3) 0.48603(13) 0.0576(7) Uani 1 1 d . . . . .
C40 C 0.86080(13) 0.7904(3) 0.49938(13) 0.0586(7) Uani 1 1 d . . . . .
C41 C 0.84526(17) 0.9023(4) 0.45424(16) 0.0773(9) Uani 1 1 d . . . . .
H41 H 0.848200 0.887989 0.415727 0.093 Uiso 1 1 calc R . . . .
C42 C 0.82599(19) 1.0313(4) 0.46543(18) 0.0872(11) Uani 1 1 d . . . . .
H42 H 0.816302 1.104447 0.435004 0.105 Uiso 1 1 calc R . . . .
C43 C 0.82086(17) 1.0534(4) 0.52200(18) 0.0770(9) Uani 1 1 d . . . . .
H43 H 0.807068 1.141554 0.529049 0.092 Uiso 1 1 calc R . . . .
C44 C 0.83579(14) 0.9472(3) 0.56857(15) 0.0624(7) Uani 1 1 d . . . . .
C45 C 0.85672(13) 0.8135(3) 0.55792(13) 0.0546(6) Uani 1 1 d . . . . .
C46 C 0.87413(13) 0.6939(3) 0.60813(12) 0.0523(6) Uani 1 1 d . . . . .
C47 C 0.90499(14) 0.5606(3) 0.59409(13) 0.0595(7) Uani 1 1 d . . . . .
C48 C 0.98157(15) 0.7971(4) 0.69149(16) 0.0802(10) Uani 1 1 d . . . . .
H48A H 1.010332 0.718467 0.698449 0.120 Uiso 1 1 calc GR . . . .
H48B H 0.997349 0.852700 0.731005 0.120 Uiso 1 1 calc GR . . . .
H48C H 0.979553 0.855308 0.656301 0.120 Uiso 1 1 calc GR . . . .
C49 C 0.90390(14) 0.6736(3) 0.71936(12) 0.0518(6) Uani 1 1 d . . . . .
C50 C 0.84474(14) 0.6032(3) 0.68785(13) 0.0535(6) Uani 1 1 d . . . . .
C51 C 0.81980(17) 0.5313(3) 0.72281(15) 0.0664(8) Uani 1 1 d . . . . .
H51 H 0.779630 0.486650 0.701379 0.080 Uiso 1 1 calc R . . . .
C52 C 0.85576(19) 0.5266(4) 0.79068(15) 0.0740(9) Uani 1 1 d . . . . .
H52 H 0.840505 0.475233 0.815165 0.089 Uiso 1 1 calc R . . . .
C53 C 0.91370(18) 0.5972(4) 0.82193(14) 0.0738(9) Uani 1 1 d . . . . .
H53 H 0.936617 0.595002 0.867638 0.089 Uiso 1 1 calc R . . . .
C54 C 0.93934(16) 0.6723(3) 0.78709(14) 0.0653(8) Uani 1 1 d . . . . .
H54 H 0.978803 0.719679 0.808703 0.078 Uiso 1 1 calc R . . . .
C55 C 0.82554(15) 0.9758(3) 0.62651(15) 0.0646(7) Uani 1 1 d . . . . .
C56 C 0.84840(18) 1.0996(4) 0.66407(18) 0.0797(9) Uani 1 1 d . . . . .
H56 H 0.872455 1.165071 0.654233 0.096 Uiso 1 1 calc R . . . .
C57 C 0.8353(2) 1.1246(4) 0.7157(2) 0.0941(12) Uani 1 1 d . . . . .
H57 H 0.851434 1.206009 0.741255 0.113 Uiso 1 1 calc R . . . .
C58 C 0.7985(2) 1.0299(5) 0.7298(2) 0.1001(13) Uani 1 1 d . . . . .
H58 H 0.791350 1.045581 0.765826 0.120 Uiso 1 1 calc R . . . .
C59 C 0.77244(19) 0.9132(4) 0.69097(19) 0.0833(10) Uani 1 1 d . . . . .
H59 H 0.745124 0.852868 0.698648 0.100 Uiso 1 1 calc R . . . .
C60 C 0.78670(15) 0.8848(3) 0.64024(15) 0.0625(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
O1 C17 1.208(4) . ?
O2 C25 1.207(3) . ?
N1 C15 1.476(3) . ?
N1 C16 1.416(4) . ?
N1 C20 1.384(3) . ?
N2 C5 1.406(4) . ?
N2 C8 1.403(3) . ?
N2 C17 1.376(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.390(5) . ?
C1 C6 1.384(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.400(4) . ?
C4 C5 1.398(4) . ?
C4 C7 1.429(4) . ?
C5 C6 1.378(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.359(4) . ?
C8 C9 1.457(4) . ?
C9 C10 1.405(4) . ?
C9 C14 1.402(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.355(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.398(4) . ?
C13 C14 1.404(4) . ?
C13 C31 1.487(4) . ?
C14 C15 1.533(4) . ?
C15 C17 1.540(4) . ?
C15 C18 1.571(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18 0.9800 . ?
C18 C19 1.520(4) . ?
C18 C25 1.513(4) . ?
C19 C20 1.381(4) . ?
C19 C24 1.365(4) . ?
C20 C21 1.392(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.364(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.387(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.492(4) . ?
C26 C27 1.391(4) . ?
C26 C31 1.394(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.376(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.373(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.373(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.392(4) . ?
O3 C011 1.218(4) . ?
O4 C47 1.206(4) . ?
N3 C46 1.464(3) . ?
N3 C48 1.435(4) . ?
N3 C49 1.388(3) . ?
N4 C36 1.412(4) . ?
N4 C39 1.394(4) . ?
N4 C47 1.377(3) . ?
C00V H00V 0.9800 . ?
C00V C011 1.518(4) . ?
C00V C46 1.571(4) . ?
C00V C50 1.519(4) . ?
C011 C60 1.500(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.362(6) . ?
C32 C37 1.397(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.375(5) . ?
C34 H34 0.9300 . ?
C34 C35 1.389(4) . ?
C35 H35 0.9300 . ?
C35 C36 1.367(5) . ?
C36 C37 1.400(4) . ?
C37 C38 1.416(5) . ?
C38 H38 0.9300 . ?
C38 C39 1.356(4) . ?
C39 C40 1.441(4) . ?
C40 C41 1.401(4) . ?
C40 C45 1.411(4) . ?
C41 H41 0.9300 . ?
C41 C42 1.360(5) . ?
C42 H42 0.9300 . ?
C42 C43 1.377(5) . ?
C43 H43 0.9300 . ?
C43 C44 1.384(4) . ?
C44 C45 1.411(4) . ?
C44 C55 1.485(4) . ?
C45 C46 1.524(4) . ?
C46 C47 1.553(4) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 C50 1.390(4) . ?
C49 C54 1.380(4) . ?
C50 C51 1.372(4) . ?
C51 H51 0.9300 . ?
C51 C52 1.384(4) . ?
C52 H52 0.9300 . ?
C52 C53 1.369(5) . ?
C53 H53 0.9300 . ?
C53 C54 1.396(4) . ?
C54 H54 0.9300 . ?
C55 C56 1.397(4) . ?
C55 C60 1.387(4) . ?
C56 H56 0.9300 . ?
C56 C57 1.380(5) . ?
C57 H57 0.9300 . ?
C57 C58 1.377(6) . ?
C58 H58 0.9300 . ?
C58 C59 1.365(5) . ?
C59 H59 0.9300 . ?
C59 C60 1.382(4) . ?

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
C16 N1 C15 121.5(2) . . ?
C20 N1 C15 109.7(2) . . ?
C20 N1 C16 124.6(3) . . ?
C8 N2 C5 109.0(2) . . ?
C17 N2 C5 126.4(3) . . ?
C17 N2 C8 124.5(2) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C6 C1 C2 120.6(4) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.7(3) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.6(3) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C7 133.5(3) . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 C7 107.4(3) . . ?
C4 C5 N2 106.9(3) . . ?
C6 C5 N2 130.9(3) . . ?
C6 C5 C4 122.2(3) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 C1 117.8(3) . . ?
C5 C6 H6 121.1 . . ?
C4 C7 H7 125.6 . . ?
C8 C7 C4 108.9(3) . . ?
C8 C7 H7 125.6 . . ?
N2 C8 C9 119.1(2) . . ?
C7 C8 N2 107.9(3) . . ?
C7 C8 C9 132.9(3) . . ?
C10 C9 C8 119.0(3) . . ?
C14 C9 C8 121.4(2) . . ?
C14 C9 C10 119.4(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C14 119.0(3) . . ?
C12 C13 C31 117.4(3) . . ?
C14 C13 C31 123.5(2) . . ?
C9 C14 C13 119.7(2) . . ?
C9 C14 C15 119.7(2) . . ?
C13 C14 C15 120.5(2) . . ?
N1 C15 C14 110.5(2) . . ?
N1 C15 C17 106.5(2) . . ?
N1 C15 C18 102.4(2) . . ?
C14 C15 C17 115.6(2) . . ?
C14 C15 C18 115.7(2) . . ?
C17 C15 C18 105.0(2) . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 N2 121.0(3) . . ?
O1 C17 C15 120.5(3) . . ?
N2 C17 C15 118.4(2) . . ?
C15 C18 H18 111.1 . . ?
C19 C18 C15 102.0(2) . . ?
C19 C18 H18 111.1 . . ?
C25 C18 C15 116.3(2) . . ?
C25 C18 H18 111.1 . . ?
C25 C18 C19 104.5(2) . . ?
C20 C19 C18 108.9(2) . . ?
C24 C19 C18 130.0(3) . . ?
C24 C19 C20 120.9(3) . . ?
N1 C20 C21 128.3(3) . . ?
C19 C20 N1 111.1(2) . . ?
C19 C20 C21 120.6(3) . . ?
C20 C21 H21 121.2 . . ?
C22 C21 C20 117.5(3) . . ?
C22 C21 H21 121.2 . . ?
C21 C22 H22 119.0 . . ?
C23 C22 C21 122.0(3) . . ?
C23 C22 H22 119.0 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 119.9(3) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C23 119.1(3) . . ?
C19 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
O2 C25 C18 122.8(3) . . ?
O2 C25 C26 121.1(3) . . ?
C26 C25 C18 115.5(2) . . ?
C27 C26 C25 120.3(3) . . ?
C27 C26 C31 120.9(3) . . ?
C31 C26 C25 118.7(3) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.2(3) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 120.2 . . ?
C29 C28 C27 119.7(3) . . ?
C29 C28 H28 120.2 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.1(3) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 119.0 . . ?
C29 C30 C31 121.9(3) . . ?
C31 C30 H30 119.0 . . ?
C26 C31 C13 121.7(3) . . ?
C30 C31 C13 121.2(3) . . ?
C30 C31 C26 117.1(3) . . ?
C48 N3 C46 121.5(2) . . ?
C49 N3 C46 109.1(2) . . ?
C49 N3 C48 122.6(2) . . ?
C39 N4 C36 108.6(2) . . ?
C47 N4 C36 126.9(3) . . ?
C47 N4 C39 124.2(3) . . ?
C011 C00V H00V 111.9 . . ?
C011 C00V C46 113.1(2) . . ?
C011 C00V C50 105.8(2) . . ?
C46 C00V H00V 111.9 . . ?
C50 C00V H00V 111.9 . . ?
C50 C00V C46 101.6(2) . . ?
O3 C011 C00V 122.1(3) . . ?
O3 C011 C60 121.3(3) . . ?
C60 C011 C00V 116.4(2) . . ?
C33 C32 H32 120.7 . . ?
C33 C32 C37 118.6(3) . . ?
C37 C32 H32 120.7 . . ?
C32 C33 H33 119.2 . . ?
C32 C33 C34 121.5(3) . . ?
C34 C33 H33 119.2 . . ?
C33 C34 H34 119.3 . . ?
C33 C34 C35 121.3(4) . . ?
C35 C34 H34 119.3 . . ?
C34 C35 H35 121.4 . . ?
C36 C35 C34 117.1(3) . . ?
C36 C35 H35 121.4 . . ?
C35 C36 N4 131.2(3) . . ?
C35 C36 C37 122.4(3) . . ?
C37 C36 N4 106.4(3) . . ?
C32 C37 C36 118.9(4) . . ?
C32 C37 C38 133.3(3) . . ?
C36 C37 C38 107.8(3) . . ?
C37 C38 H38 125.6 . . ?
C39 C38 C37 108.7(3) . . ?
C39 C38 H38 125.6 . . ?
N4 C39 C40 120.1(2) . . ?
C38 C39 N4 108.4(3) . . ?
C38 C39 C40 131.5(3) . . ?
C41 C40 C39 119.9(3) . . ?
C41 C40 C45 118.8(3) . . ?
C45 C40 C39 121.2(3) . . ?
C40 C41 H41 119.2 . . ?
C42 C41 C40 121.5(3) . . ?
C42 C41 H41 119.2 . . ?
C41 C42 H42 120.1 . . ?
C41 C42 C43 119.8(3) . . ?
C43 C42 H42 120.1 . . ?
C42 C43 H43 119.3 . . ?
C42 C43 C44 121.4(3) . . ?
C44 C43 H43 119.3 . . ?
C43 C44 C45 119.4(3) . . ?
C43 C44 C55 118.4(3) . . ?
C45 C44 C55 122.1(3) . . ?
C40 C45 C44 119.1(3) . . ?
C40 C45 C46 119.8(3) . . ?
C44 C45 C46 121.1(2) . . ?
N3 C46 C00V 103.21(19) . . ?
N3 C46 C45 111.1(2) . . ?
N3 C46 C47 108.3(2) . . ?
C45 C46 C00V 113.3(2) . . ?
C45 C46 C47 115.0(2) . . ?
C47 C46 C00V 105.2(2) . . ?
O4 C47 N4 121.3(3) . . ?
O4 C47 C46 120.3(2) . . ?
N4 C47 C46 118.4(2) . . ?
N3 C48 H48A 109.5 . . ?
N3 C48 H48B 109.5 . . ?
N3 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
N3 C49 C50 111.3(2) . . ?
C54 C49 N3 128.1(3) . . ?
C54 C49 C50 120.5(3) . . ?
C49 C50 C00V 108.4(2) . . ?
C51 C50 C00V 130.0(3) . . ?
C51 C50 C49 121.3(3) . . ?
C50 C51 H51 120.7 . . ?
C50 C51 C52 118.5(3) . . ?
C52 C51 H51 120.7 . . ?
C51 C52 H52 119.9 . . ?
C53 C52 C51 120.3(3) . . ?
C53 C52 H52 119.9 . . ?
C52 C53 H53 119.1 . . ?
C52 C53 C54 121.8(3) . . ?
C54 C53 H53 119.1 . . ?
C49 C54 C53 117.5(3) . . ?
C49 C54 H54 121.3 . . ?
C53 C54 H54 121.3 . . ?
C56 C55 C44 122.0(3) . . ?
C60 C55 C44 119.4(3) . . ?
C60 C55 C56 118.3(3) . . ?
C55 C56 H56 120.0 . . ?
C57 C56 C55 120.0(4) . . ?
C57 C56 H56 120.0 . . ?
C56 C57 H57 119.8 . . ?
C58 C57 C56 120.5(4) . . ?
C58 C57 H57 119.8 . . ?
C57 C58 H58 120.0 . . ?
C59 C58 C57 120.1(4) . . ?
C59 C58 H58 120.0 . . ?
C58 C59 H59 120.0 . . ?
C58 C59 C60 119.9(4) . . ?
C60 C59 H59 120.0 . . ?
C55 C60 C011 119.3(3) . . ?
C59 C60 C011 119.6(3) . . ?
C59 C60 C55 121.0(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 1.748
_oxdiff_exptl_absorpt_empirical_full_min 0.752
