# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

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

data_zhangmch_220317_auto
_database_code_depnum_ccdc_archive 'CCDC 2218806'
loop_
_audit_author_name
_audit_author_address
'MC zhang'
;sysu
China
;
_audit_update_record             
;
2022-11-10 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;
_audit_creation_date             2022-03-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H26 N2 O3'
_chemical_formula_sum            'C31 H26 N2 O3'
_chemical_formula_weight         474.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
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                   10.81370(10)
_cell_length_b                   19.1942(3)
_cell_length_c                   11.7185(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.9290(10)
_cell_angle_gamma                90
_cell_volume                     2430.92(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12421
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.3550
_cell_measurement_theta_min      2.2830
_shelx_estimated_absorpt_T_max   0.825
_shelx_estimated_absorpt_T_min   0.753
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16069
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.319
_diffrn_reflns_theta_min         4.090
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     89.00 178.00   0.50    0.05    --  104.88  61.00 -30.00  178
  2  ω    127.00 167.00   0.50    0.05    --  104.88  45.00  30.00   80
  3  ω     86.00 178.00   0.50    0.05    --  104.88  85.00  69.00  184
  4  ω     80.00 109.00   0.50    0.05    --  104.88 125.00   0.00   58
  5  ω    136.00 163.00   0.50    0.05    --  104.88 125.00   0.00   54
  6  ω   -103.00 -27.00   0.50    0.05    -- -100.00  77.00  30.00  152
  7  ω   -107.00 -51.00   0.50    0.05    -- -100.00  85.00  69.00  112
  8  ω    -67.00 -36.00   0.50    0.05    -- -100.00  61.00  30.00   62
  9  ω    -23.00  27.00   0.50    0.05    --  -45.56  85.00  69.00  100
 10  ω    -68.00 -27.00   0.50    0.05    -- -100.00  61.00 -90.00   82
 11  ω   -173.00-129.00   0.50    0.05    -- -100.00 -85.00 -49.00   88
 12  ω   -173.00 -84.00   0.50    0.05    -- -100.00 -45.00  30.00  178
 13  ω    -23.00  32.00   0.50    0.05    --  -45.56  19.00  60.00  110
 14  ω    -22.00  27.00   0.50    0.05    --  -45.56  38.00 -60.00   98
 15  ω    -41.00  29.00   0.50    0.05    --  -45.56  38.00-180.00  140
 16  ω     12.00  54.00   0.50    0.05    --   45.56 -85.00 -49.00   84
 17  ω     58.00  83.00   0.50    0.05    --  104.88 -85.00 -49.00   50
 18  ω     33.00  64.00   0.50    0.05    --  104.88 -61.00-150.00   62
 19  ω     32.00  67.00   0.50    0.05    --  104.88 -61.00-120.00   70
 20  ω     36.00  73.00   0.50    0.05    --  104.88 -61.00  90.00   74
 21  ω     48.00  73.00   0.50    0.05    --  104.88 -61.00 120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0681277000
_diffrn_orient_matrix_UB_12      0.0702457000
_diffrn_orient_matrix_UB_13      -0.0080298000
_diffrn_orient_matrix_UB_21      -0.0153540000
_diffrn_orient_matrix_UB_22      0.0117021000
_diffrn_orient_matrix_UB_23      0.1288311000
_diffrn_orient_matrix_UB_31      0.1242497000
_diffrn_orient_matrix_UB_32      -0.0370053000
_diffrn_orient_matrix_UB_33      0.0254376000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4518
_reflns_number_total             4808
_reflns_odcompleteness_completeness 99.89
_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 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.115
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4808
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      1.147
_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)+(0.0366P)²+3.5108P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1466
_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 Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C25(H25), C2(H2), C5(H5), C36(H36), C28(H28), C3(H3), C4(H4),
 C22(H22), C27(H27), C32(H32), C26(H26), C18(H18), C21(H21), C20(H20), C19(H19),
  C35(H35), C33(H33), C34(H34)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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
O14 O 0.27550(15) 0.09866(8) 0.50462(15) 0.0285(4) Uani 1 1 d . . . . .
O23 O 0.75387(16) 0.33392(9) 0.51559(15) 0.0328(4) Uani 1 1 d . . . . .
O30 O 0.53654(17) 0.28263(10) 0.67815(14) 0.0356(4) Uani 1 1 d . . . . .
N24 N 0.57155(17) 0.23204(10) 0.50489(15) 0.0217(4) Uani 1 1 d . . . . .
N9 N 0.68874(17) 0.43640(10) 0.43195(16) 0.0246(4) Uani 1 1 d . . . . .
C7 C 0.5422(2) 0.34912(12) 0.43557(18) 0.0221(4) Uani 1 1 d . . . . .
C10 C 0.4968(2) 0.28394(12) 0.44611(18) 0.0221(4) Uani 1 1 d . . . . .
C11 C 0.3816(2) 0.26189(11) 0.38896(18) 0.0231(5) Uani 1 1 d . . . . .
H11 H 0.360736 0.287161 0.321313 0.028 Uiso 1 1 calc R U . . .
C1 C 0.5786(2) 0.46278(12) 0.38218(18) 0.0241(5) Uani 1 1 d . . . . .
C29 C 0.5942(2) 0.23794(12) 0.62274(18) 0.0243(5) Uani 1 1 d . . . . .
C6 C 0.4865(2) 0.41085(12) 0.38259(18) 0.0233(5) Uani 1 1 d . . . . .
C8 C 0.6729(2) 0.36919(12) 0.46933(19) 0.0243(5) Uani 1 1 d . . . . .
C12 C 0.2993(2) 0.21202(12) 0.41494(19) 0.0236(5) Uani 1 1 d . . . . .
C25 C 0.6275(2) 0.18285(12) 0.43790(19) 0.0246(5) Uani 1 1 d . . . . .
H25 H 0.610249 0.181827 0.357888 0.030 Uiso 1 1 calc R U . . .
C13 C 0.2985(2) 0.17054(12) 0.52438(19) 0.0255(5) Uani 1 1 d . . . . .
H13A H 0.379490 0.175903 0.565420 0.031 Uiso 1 1 calc R U . . .
H13B H 0.234028 0.189408 0.573785 0.031 Uiso 1 1 calc R U . . .
C2 C 0.5552(2) 0.52945(13) 0.3427(2) 0.0297(5) Uani 1 1 d . . . . .
H2 H 0.618367 0.563873 0.343417 0.036 Uiso 1 1 calc R U . . .
C5 C 0.3678(2) 0.42735(12) 0.34152(19) 0.0259(5) Uani 1 1 d . . . . .
H5 H 0.303973 0.393342 0.341450 0.031 Uiso 1 1 calc R U . . .
C17 C 0.8909(2) 0.46089(12) 0.3474(2) 0.0255(5) Uani 1 1 d . . . . .
C31 C 0.1953(2) 0.19953(11) 0.3316(2) 0.0257(5) Uani 1 1 d . . . . .
C16 C 0.8069(2) 0.47323(13) 0.4461(2) 0.0276(5) Uani 1 1 d . . . . .
H16A H 0.849351 0.457579 0.517711 0.033 Uiso 1 1 calc R U . . .
H16B H 0.790782 0.523802 0.452922 0.033 Uiso 1 1 calc R U . . .
C36 C 0.2186(2) 0.19503(12) 0.2151(2) 0.0277(5) Uani 1 1 d . . . . .
H36 H 0.301356 0.196911 0.190494 0.033 Uiso 1 1 calc R U . . .
C28 C 0.6802(2) 0.18869(13) 0.6703(2) 0.0280(5) Uani 1 1 d . . . . .
H28 H 0.700442 0.190468 0.749807 0.034 Uiso 1 1 calc R U . . .
C3 C 0.4353(2) 0.54450(13) 0.3015(2) 0.0325(5) Uani 1 1 d . . . . .
H3 H 0.416515 0.589930 0.273803 0.039 Uiso 1 1 calc R U . . .
C4 C 0.3437(2) 0.49433(13) 0.3005(2) 0.0298(5) Uani 1 1 d . . . . .
H4 H 0.263064 0.505625 0.271423 0.036 Uiso 1 1 calc R U . . .
C22 C 0.8999(2) 0.50940(12) 0.2603(2) 0.0298(5) Uani 1 1 d . . . . .
H22 H 0.853443 0.551341 0.262859 0.036 Uiso 1 1 calc R U . . .
C27 C 0.7340(2) 0.13927(13) 0.6054(2) 0.0314(5) Uani 1 1 d . . . . .
H27 H 0.789879 0.106821 0.640078 0.038 Uiso 1 1 calc R U . . .
C32 C 0.0725(2) 0.19466(13) 0.3659(2) 0.0316(5) Uani 1 1 d . . . . .
H32 H 0.055136 0.195246 0.444824 0.038 Uiso 1 1 calc R U . . .
C26 C 0.7074(2) 0.13577(13) 0.4866(2) 0.0305(5) Uani 1 1 d . . . . .
H26 H 0.744765 0.101067 0.441359 0.037 Uiso 1 1 calc R U . . .
C18 C 0.9595(2) 0.39932(13) 0.3418(2) 0.0297(5) Uani 1 1 d . . . . .
H18 H 0.954059 0.365551 0.400733 0.036 Uiso 1 1 calc R U . . .
C21 C 0.9766(2) 0.49718(13) 0.1691(2) 0.0332(6) Uani 1 1 d . . . . .
H21 H 0.982369 0.530848 0.110101 0.040 Uiso 1 1 calc R U . . .
C20 C 1.0441(2) 0.43631(14) 0.1643(2) 0.0332(6) Uani 1 1 d . . . . .
H20 H 1.096272 0.428011 0.102087 0.040 Uiso 1 1 calc R U . . .
C19 C 1.0356(2) 0.38723(14) 0.2507(2) 0.0335(6) Uani 1 1 d . . . . .
H19 H 1.081893 0.345257 0.247489 0.040 Uiso 1 1 calc R U . . .
C35 C 0.1211(2) 0.18780(13) 0.1349(2) 0.0346(6) Uani 1 1 d . . . . .
H35 H 0.137830 0.184349 0.056024 0.041 Uiso 1 1 calc R U . . .
C33 C -0.0234(2) 0.18900(14) 0.2850(3) 0.0395(6) Uani 1 1 d . . . . .
H33 H -0.106451 0.187398 0.308906 0.047 Uiso 1 1 calc R U . . .
C34 C 0.0005(3) 0.18565(14) 0.1699(3) 0.0416(7) Uani 1 1 d . . . . .
H34 H -0.065929 0.181893 0.115024 0.050 Uiso 1 1 calc R U . . .
C15 C 0.3797(3) 0.06396(14) 0.4632(3) 0.0463(7) Uani 1 1 d . . . . .
H15A H 0.407587 0.087801 0.394711 0.069 Uiso 1 1 calc R U . . .
H15B H 0.357546 0.015743 0.444044 0.069 Uiso 1 1 calc R U . . .
H15C H 0.446345 0.064201 0.521923 0.069 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
O14 C13 1.419(3) . ?
O14 C15 1.409(3) . ?
O23 C8 1.219(3) . ?
O30 C29 1.255(3) . ?
N24 C10 1.443(3) . ?
N24 C29 1.399(3) . ?
N24 C25 1.380(3) . ?
N9 C1 1.403(3) . ?
N9 C8 1.375(3) . ?
N9 C16 1.465(3) . ?
C7 C10 1.351(3) . ?
C7 C6 1.459(3) . ?
C7 C8 1.505(3) . ?
C10 C11 1.458(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.349(3) . ?
C1 C6 1.410(3) . ?
C1 C2 1.381(3) . ?
C29 C28 1.426(3) . ?
C6 C5 1.392(3) . ?
C12 C13 1.510(3) . ?
C12 C31 1.484(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.362(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C2 H2 0.9500 . ?
C2 C3 1.399(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.394(3) . ?
C17 C16 1.513(3) . ?
C17 C22 1.387(3) . ?
C17 C18 1.398(3) . ?
C31 C36 1.399(3) . ?
C31 C32 1.403(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C36 H36 0.9500 . ?
C36 C35 1.395(3) . ?
C28 H28 0.9500 . ?
C28 C27 1.359(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9500 . ?
C22 H22 0.9500 . ?
C22 C21 1.395(3) . ?
C27 H27 0.9500 . ?
C27 C26 1.413(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.386(4) . ?
C26 H26 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.390(4) . ?
C21 H21 0.9500 . ?
C21 C20 1.380(4) . ?
C20 H20 0.9500 . ?
C20 C19 1.388(4) . ?
C19 H19 0.9500 . ?
C35 H35 0.9500 . ?
C35 C34 1.382(4) . ?
C33 H33 0.9500 . ?
C33 C34 1.384(4) . ?
C34 H34 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O14 C13 112.19(19) . . ?
C29 N24 C10 119.47(18) . . ?
C25 N24 C10 116.72(18) . . ?
C25 N24 C29 123.45(19) . . ?
C1 N9 C16 126.71(19) . . ?
C8 N9 C1 110.98(18) . . ?
C8 N9 C16 122.3(2) . . ?
C10 C7 C6 130.2(2) . . ?
C10 C7 C8 123.6(2) . . ?
C6 C7 C8 105.96(18) . . ?
N24 C10 C11 118.37(19) . . ?
C7 C10 N24 118.93(19) . . ?
C7 C10 C11 122.3(2) . . ?
C10 C11 H11 114.2 . . ?
C12 C11 C10 131.5(2) . . ?
C12 C11 H11 114.2 . . ?
N9 C1 C6 109.49(19) . . ?
C2 C1 N9 128.1(2) . . ?
C2 C1 C6 122.3(2) . . ?
O30 C29 N24 119.5(2) . . ?
O30 C29 C28 125.4(2) . . ?
N24 C29 C28 115.0(2) . . ?
C1 C6 C7 107.08(19) . . ?
C5 C6 C7 134.0(2) . . ?
C5 C6 C1 118.8(2) . . ?
O23 C8 N9 124.6(2) . . ?
O23 C8 C7 128.9(2) . . ?
N9 C8 C7 106.40(19) . . ?
C11 C12 C13 126.0(2) . . ?
C11 C12 C31 117.2(2) . . ?
C31 C12 C13 116.64(19) . . ?
N24 C25 H25 120.0 . . ?
C26 C25 N24 120.0(2) . . ?
C26 C25 H25 120.0 . . ?
O14 C13 C12 112.33(18) . . ?
O14 C13 H13A 109.1 . . ?
O14 C13 H13B 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C1 C2 H2 121.2 . . ?
C1 C2 C3 117.7(2) . . ?
C3 C2 H2 121.2 . . ?
C6 C5 H5 120.4 . . ?
C6 C5 C4 119.3(2) . . ?
C4 C5 H5 120.4 . . ?
C22 C17 C16 121.0(2) . . ?
C22 C17 C18 118.9(2) . . ?
C18 C17 C16 120.1(2) . . ?
C36 C31 C12 119.6(2) . . ?
C36 C31 C32 118.6(2) . . ?
C32 C31 C12 121.7(2) . . ?
N9 C16 C17 112.47(18) . . ?
N9 C16 H16A 109.1 . . ?
N9 C16 H16B 109.1 . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C31 C36 H36 119.8 . . ?
C35 C36 C31 120.4(2) . . ?
C35 C36 H36 119.8 . . ?
C29 C28 H28 119.0 . . ?
C27 C28 C29 121.9(2) . . ?
C27 C28 H28 119.0 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C5 C4 H4 119.5 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4 119.5 . . ?
C17 C22 H22 119.7 . . ?
C17 C22 C21 120.6(2) . . ?
C21 C22 H22 119.7 . . ?
C28 C27 H27 119.7 . . ?
C28 C27 C26 120.6(2) . . ?
C26 C27 H27 119.7 . . ?
C31 C32 H32 119.9 . . ?
C33 C32 C31 120.2(3) . . ?
C33 C32 H32 119.9 . . ?
C25 C26 C27 119.1(2) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 H26 120.5 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C22 C21 H21 119.9 . . ?
C20 C21 C22 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C21 C20 H20 120.1 . . ?
C21 C20 C19 119.8(2) . . ?
C19 C20 H20 120.1 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C36 C35 H35 119.9 . . ?
C34 C35 C36 120.2(3) . . ?
C34 C35 H35 119.9 . . ?
C32 C33 H33 119.6 . . ?
C34 C33 C32 120.7(3) . . ?
C34 C33 H33 119.6 . . ?
C35 C34 C33 119.8(2) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
O30 C29 C28 C27 176.3(2) . . . . ?
N24 C10 C11 C12 33.5(4) . . . . ?
N24 C29 C28 C27 -1.0(3) . . . . ?
N24 C25 C26 C27 -1.5(4) . . . . ?
N9 C1 C6 C7 0.1(2) . . . . ?
N9 C1 C6 C5 177.11(19) . . . . ?
N9 C1 C2 C3 -176.7(2) . . . . ?
C7 C10 C11 C12 -153.8(2) . . . . ?
C7 C6 C5 C4 176.5(2) . . . . ?
C10 N24 C29 O30 9.4(3) . . . . ?
C10 N24 C29 C28 -173.20(19) . . . . ?
C10 N24 C25 C26 174.6(2) . . . . ?
C10 C7 C6 C1 -172.7(2) . . . . ?
C10 C7 C6 C5 10.9(4) . . . . ?
C10 C7 C8 O23 -4.7(4) . . . . ?
C10 C7 C8 N9 172.1(2) . . . . ?
C10 C11 C12 C13 8.8(4) . . . . ?
C10 C11 C12 C31 -175.1(2) . . . . ?
C11 C12 C13 O14 -136.5(2) . . . . ?
C11 C12 C31 C36 45.2(3) . . . . ?
C11 C12 C31 C32 -132.3(2) . . . . ?
C1 N9 C8 O23 179.8(2) . . . . ?
C1 N9 C8 C7 2.9(2) . . . . ?
C1 N9 C16 C17 -92.6(3) . . . . ?
C1 C6 C5 C4 0.5(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C29 N24 C10 C7 68.9(3) . . . . ?
C29 N24 C10 C11 -118.2(2) . . . . ?
C29 N24 C25 C26 1.5(3) . . . . ?
C29 C28 C27 C26 1.0(4) . . . . ?
C6 C7 C10 N24 -179.0(2) . . . . ?
C6 C7 C10 C11 8.4(4) . . . . ?
C6 C7 C8 O23 -179.5(2) . . . . ?
C6 C7 C8 N9 -2.7(2) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C6 C5 C4 C3 -0.8(3) . . . . ?
C8 N9 C1 C6 -2.0(3) . . . . ?
C8 N9 C1 C2 174.8(2) . . . . ?
C8 N9 C16 C17 88.3(3) . . . . ?
C8 C7 C10 N24 7.6(3) . . . . ?
C8 C7 C10 C11 -165.1(2) . . . . ?
C8 C7 C6 C1 1.6(2) . . . . ?
C8 C7 C6 C5 -174.8(2) . . . . ?
C12 C31 C36 C35 -175.9(2) . . . . ?
C12 C31 C32 C33 174.4(2) . . . . ?
C25 N24 C10 C7 -104.5(2) . . . . ?
C25 N24 C10 C11 68.4(3) . . . . ?
C25 N24 C29 O30 -177.7(2) . . . . ?
C25 N24 C29 C28 -0.3(3) . . . . ?
C13 C12 C31 C36 -138.4(2) . . . . ?
C13 C12 C31 C32 44.1(3) . . . . ?
C2 C1 C6 C7 -176.9(2) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C17 C22 C21 C20 0.3(4) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C31 C12 C13 O14 47.4(3) . . . . ?
C31 C36 C35 C34 0.6(4) . . . . ?
C31 C32 C33 C34 2.2(4) . . . . ?
C16 N9 C1 C6 178.8(2) . . . . ?
C16 N9 C1 C2 -4.4(4) . . . . ?
C16 N9 C8 O23 -0.9(3) . . . . ?
C16 N9 C8 C7 -177.86(19) . . . . ?
C16 C17 C22 C21 -179.3(2) . . . . ?
C16 C17 C18 C19 179.1(2) . . . . ?
C36 C31 C32 C33 -3.1(4) . . . . ?
C36 C35 C34 C33 -1.6(4) . . . . ?
C28 C27 C26 C25 0.3(4) . . . . ?
C22 C17 C16 N9 99.2(3) . . . . ?
C22 C17 C18 C19 0.2(4) . . . . ?
C22 C21 C20 C19 -0.1(4) . . . . ?
C32 C31 C36 C35 1.8(3) . . . . ?
C32 C33 C34 C35 0.2(4) . . . . ?
C18 C17 C16 N9 -79.7(3) . . . . ?
C18 C17 C22 C21 -0.3(4) . . . . ?
C21 C20 C19 C18 -0.1(4) . . . . ?
C15 O14 C13 C12 75.5(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 2.115
_oxdiff_exptl_absorpt_empirical_full_min 0.469
####################################################################### 
# 
# 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_20221010-zmc-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2218836'
loop_
_audit_author_name
_audit_author_address
'MC zhang'
;sysu
China
;
_audit_update_record             
;
2022-11-10 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;
_audit_creation_date             2022-10-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H26 Br2 N2 O3'
_chemical_formula_sum            'C32 H26 Br2 N2 O3'
_chemical_formula_weight         646.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Br'
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'
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      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                   8.44480(10)
_cell_length_b                   12.1329(2)
_cell_length_c                   13.4054(2)
_cell_angle_alpha                86.2290(10)
_cell_angle_beta                 88.8050(10)
_cell_angle_gamma                71.450(2)
_cell_volume                     1299.34(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14189
_cell_measurement_temperature    99.97(17)
_cell_measurement_theta_max      74.7760
_cell_measurement_theta_min      3.8140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.272
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.60a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16026
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.345
_diffrn_reflns_theta_min         3.304
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(17)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     65.00 103.00   0.50    0.15    --   44.84-145.00 -31.00   76
  2  ω     98.00 127.00   0.50    0.15    --  105.85-145.00 -31.00   58
  3  ω     70.00  97.00   0.50    0.15    --  105.85-125.00 135.00   54
  4  ω     42.00  67.00   0.50    0.15    --  105.85-125.00 135.00   50
  5  ω     21.00  95.00   0.50    0.15    --   44.84-125.00 135.00  148
  6  ω     33.00 105.00   0.50    0.15    --  105.85 -94.00 150.00  144
  7  ω     77.00 102.00   0.50    0.15    --  105.85-125.00   0.00   50
  8  ω     41.00  73.00   0.50    0.15    --  105.85-125.00   0.00   64
  9  ω     87.00 112.00   0.50    0.15    --  105.85-125.00-150.00   50
 10  ω     39.00 106.00   0.50    0.15    --  105.85 -94.00-120.00  134
 11  ω     39.00 102.00   0.50    0.15    --  105.85 -77.00 -30.00  126
 12  ω     39.00  67.00   0.50    0.15    --  105.85 -61.00 -30.00   56
 13  ω     33.00  73.00   0.50    0.15    --  105.85 -61.00 -90.00   80
 14  ω     33.00  70.00   0.50    0.15    --  105.85 -61.00-180.00   74
 15  ω    -31.00  25.00   0.50    0.15    --   44.84 -19.00-120.00  112
 16  ω    104.00 129.00   0.50    0.15    --  105.85 125.00-147.00   50
 17  ω     89.00 122.00   0.50    0.15    --  105.85 145.00  19.00   66
 18  ω     67.00  92.00   0.50    0.15    --   44.84 145.00  19.00   50
 19  ω     81.00 177.00   0.50    0.15    --  105.85  15.00  90.00  192
 20  ω    124.00 178.00   0.50    0.15    --  105.85  45.00-150.00  108
 21  ω     20.00 118.00   0.50    0.15    --   44.84  77.00-150.00  196
 22  ω     -2.00  23.00   0.50    0.15    --  -44.84  19.00-180.00   50
 23  ω    -23.00  32.00   0.50    0.15    --  -44.84  19.00-150.00  110
 24  ω    -58.00 -26.00   0.50    0.15    -- -100.00  61.00-180.00   64
 25  ω    -84.00 -58.00   0.50    0.15    -- -100.00  77.00-120.00   52
 26  ω    -24.00  32.00   0.50    0.15    --  -44.84  19.00  90.00  112
 27  ω   -108.00 -47.00   0.50    0.15    -- -100.00 110.00 148.42  122
 28  ω    -89.00 -64.00   0.50    0.15    --  -44.84 145.00  19.00   50
 29  ω   -123.00 -57.00   0.50    0.15    -- -100.00 145.00  19.00  132
 30  ω   -108.00 -67.00   0.50    0.15    -- -100.00 125.00   0.00   82
 31  ω    -79.00 -54.00   0.50    0.15    --  -44.84 125.00-147.00   50
 32  ω   -112.00 -81.00   0.50    0.15    -- -100.00 125.00-147.00   62
 33  ω   -173.00 -81.00   0.50    0.15    -- -100.00 -61.00-150.00  184
 34  ω   -173.00-127.00   0.50    0.15    -- -100.00 -30.00-180.00   92
 35  ω   -112.00 -82.00   0.50    0.15    -- -100.00 -30.00-180.00   60
 36  ω   -171.00 -83.00   0.50    0.15    -- -100.00 -45.00  30.00  176
 37  ω   -173.00 -96.00   0.50    0.15    -- -100.00 -94.00   0.00  154
 38  ω   -139.00-114.00   0.50    0.15    -- -100.00-145.00 -31.00   50
 39  ω    -91.00 -66.00   0.50    0.15    --  -44.84-145.00 -31.00   50
 40  ω   -159.00-105.00   0.50    0.15    -- -100.00-125.00 135.00  108
 41  ω   -171.00-139.00   0.50    0.15    -- -100.00 -94.00 150.00   64
 42  ω   -135.00-104.00   0.50    0.15    -- -100.00 -94.00 150.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0204147000
_diffrn_orient_matrix_UB_12      -0.0046558000
_diffrn_orient_matrix_UB_13      -0.1142636000
_diffrn_orient_matrix_UB_21      0.0764276000
_diffrn_orient_matrix_UB_22      -0.1335752000
_diffrn_orient_matrix_UB_23      0.0119301000
_diffrn_orient_matrix_UB_31      -0.1754133000
_diffrn_orient_matrix_UB_32      -0.0119983000
_diffrn_orient_matrix_UB_33      -0.0081096000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5048
_reflns_number_total             5119
_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 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         2.210
_refine_diff_density_min         -1.122
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         5119
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0449
_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)+(0.0695P)²+3.8826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1275
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28), C30(H30)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C27(H27A,H27B,H27C)
;
_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
Br Br -0.03030(4) 0.19444(3) 0.17006(3) 0.02548(13) Uani 1 1 d . . . . .
Br1 Br 0.56773(5) 0.14881(3) -0.04860(3) 0.03248(14) Uani 1 1 d . . . . .
O1 O 0.6167(3) 0.1819(2) 0.29234(19) 0.0297(6) Uani 1 1 d . . . . .
O2 O 0.1167(3) 0.3513(2) 0.2845(2) 0.0325(6) Uani 1 1 d . . . . .
O3 O 0.3129(4) 0.5241(3) 0.0167(2) 0.0372(6) Uani 1 1 d . . . . .
N1 N 0.7440(3) 0.2753(3) 0.3931(2) 0.0241(6) Uani 1 1 d . . . . .
N2 N 0.3462(3) 0.3401(2) 0.1866(2) 0.0185(5) Uani 1 1 d . . . . .
C1 C 0.7222(4) 0.3899(3) 0.4168(2) 0.0231(7) Uani 1 1 d . . . . .
C2 C 0.8136(4) 0.4300(4) 0.4824(3) 0.0295(8) Uani 1 1 d . . . . .
H2 H 0.9068 0.3778 0.5176 0.035 Uiso 1 1 calc R U . . .
C3 C 0.7642(5) 0.5490(4) 0.4949(3) 0.0318(8) Uani 1 1 d . . . . .
H3 H 0.8229 0.5781 0.5408 0.038 Uiso 1 1 calc R U . . .
C4 C 0.6315(5) 0.6258(4) 0.4418(3) 0.0315(8) Uani 1 1 d . . . . .
C5 C 0.6411(6) 0.7433(4) 0.4762(4) 0.0495(11) Uani 1 1 d . . . . .
H5A H 0.6195 0.7473 0.5482 0.074 Uiso 1 1 calc R U . . .
H5B H 0.5573 0.8079 0.4401 0.074 Uiso 1 1 calc R U . . .
H5C H 0.7527 0.7489 0.4619 0.074 Uiso 1 1 calc R U . . .
C6 C 0.5428(4) 0.5857(3) 0.3738(3) 0.0250(7) Uani 1 1 d . . . . .
H6 H 0.4542 0.6390 0.3358 0.030 Uiso 1 1 calc R U . . .
C7 C 0.5857(4) 0.4666(3) 0.3625(2) 0.0207(6) Uani 1 1 d . . . . .
C8 C 0.5181(4) 0.3949(3) 0.3028(2) 0.0199(6) Uani 1 1 d . . . . .
C9 C 0.6275(4) 0.2709(3) 0.3253(2) 0.0226(7) Uani 1 1 d . . . . .
C10 C 0.8719(4) 0.1701(3) 0.4341(3) 0.0287(8) Uani 1 1 d . . . . .
H10A H 0.9691 0.1910 0.4563 0.034 Uiso 1 1 calc R U . . .
H10B H 0.9103 0.1145 0.3810 0.034 Uiso 1 1 calc R U . . .
C11 C 0.8060(4) 0.1119(3) 0.5216(3) 0.0248(7) Uani 1 1 d . . . . .
C12 C 0.7305(5) 0.0283(4) 0.5057(3) 0.0355(9) Uani 1 1 d . . . . .
H12 H 0.7233 0.0058 0.4399 0.043 Uiso 1 1 calc R U . . .
C13 C 0.6650(6) -0.0231(4) 0.5856(4) 0.0430(10) Uani 1 1 d . . . . .
H13 H 0.6149 -0.0810 0.5741 0.052 Uiso 1 1 calc R U . . .
C14 C 0.6731(5) 0.0104(4) 0.6811(3) 0.0394(10) Uani 1 1 d . . . . .
H14 H 0.6248 -0.0221 0.7354 0.047 Uiso 1 1 calc R U . . .
C15 C 0.7515(5) 0.0913(4) 0.6976(3) 0.0379(9) Uani 1 1 d . . . . .
H15 H 0.7606 0.1126 0.7637 0.045 Uiso 1 1 calc R U . . .
C16 C 0.8171(5) 0.1415(3) 0.6186(3) 0.0313(8) Uani 1 1 d . . . . .
H16 H 0.8706 0.1973 0.6309 0.038 Uiso 1 1 calc R U . . .
C17 C 0.3802(4) 0.4265(3) 0.2444(2) 0.0189(6) Uani 1 1 d . . . . .
C18 C 0.2547(4) 0.5416(3) 0.2401(2) 0.0208(6) Uani 1 1 d . . . . .
H18 H 0.2395 0.5820 0.2997 0.025 Uiso 1 1 calc R U . . .
C19 C 0.1577(4) 0.5978(3) 0.1625(3) 0.0232(7) Uani 1 1 d . . . . .
C20 C 0.0240(4) 0.7090(3) 0.1786(3) 0.0243(7) Uani 1 1 d . . . . .
C21 C -0.0924(5) 0.7158(3) 0.2554(3) 0.0337(8) Uani 1 1 d . . . . .
H21 H -0.0877 0.6486 0.2973 0.040 Uiso 1 1 calc R U . . .
C22 C -0.2153(5) 0.8212(4) 0.2702(4) 0.0450(11) Uani 1 1 d . . . . .
H22 H -0.2957 0.8246 0.3215 0.054 Uiso 1 1 calc R U . . .
C23 C -0.2230(5) 0.9201(4) 0.2125(4) 0.0445(11) Uani 1 1 d . . . . .
H23 H -0.3054 0.9920 0.2249 0.053 Uiso 1 1 calc R U . . .
C24 C -0.1089(6) 0.9137(3) 0.1358(3) 0.0387(10) Uani 1 1 d . . . . .
H24 H -0.1139 0.9818 0.0951 0.046 Uiso 1 1 calc R U . . .
C25 C 0.0133(5) 0.8089(3) 0.1174(3) 0.0291(8) Uani 1 1 d . . . . .
H25 H 0.0891 0.8053 0.0634 0.035 Uiso 1 1 calc R U . . .
C26 C 0.1522(5) 0.5547(4) 0.0592(3) 0.0357(9) Uani 1 1 d . . . . .
H26A H 0.1122 0.4862 0.0643 0.043 Uiso 1 1 calc R U . . .
H26B H 0.0736 0.6166 0.0161 0.043 Uiso 1 1 calc R U . . .
C27 C 0.3040(6) 0.4799(4) -0.0801(3) 0.0421(10) Uani 1 1 d . . . . .
H27A H 0.2507 0.4189 -0.0730 0.063 Uiso 1 1 calc R U . . .
H27B H 0.4170 0.4474 -0.1069 0.063 Uiso 1 1 calc R U . . .
H27C H 0.2382 0.5435 -0.1259 0.063 Uiso 1 1 calc R U . . .
C28 C 0.4561(4) 0.2908(3) 0.1128(2) 0.0202(6) Uani 1 1 d . . . . .
H28 H 0.5548 0.3114 0.1011 0.024 Uiso 1 1 calc R U . . .
C29 C 0.4214(4) 0.2120(3) 0.0567(2) 0.0229(7) Uani 1 1 d . . . . .
C30 C 0.2753(4) 0.1815(3) 0.0727(2) 0.0218(7) Uani 1 1 d . . . . .
H30 H 0.2513 0.1272 0.0324 0.026 Uiso 1 1 calc R U . . .
C31 C 0.1689(4) 0.2308(3) 0.1465(2) 0.0204(6) Uani 1 1 d . . . . .
C32 C 0.2008(4) 0.3111(3) 0.2118(2) 0.0189(6) 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
Br C31 1.885(3) . ?
Br1 C29 1.890(3) . ?
O1 C9 1.223(4) . ?
O2 C32 1.226(4) . ?
O3 C26 1.407(5) . ?
O3 C27 1.449(5) . ?
N1 C1 1.400(5) . ?
N1 C9 1.369(4) . ?
N1 C10 1.468(4) . ?
N2 C17 1.446(4) . ?
N2 C28 1.373(4) . ?
N2 C32 1.410(4) . ?
C1 C2 1.389(5) . ?
C1 C7 1.410(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(6) . ?
C4 C5 1.553(6) . ?
C4 C6 1.396(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6 0.9500 . ?
C6 C7 1.391(5) . ?
C7 C8 1.466(5) . ?
C8 C9 1.508(4) . ?
C8 C17 1.353(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.515(5) . ?
C11 C12 1.388(6) . ?
C11 C16 1.385(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.395(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.459(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.344(5) . ?
C19 C20 1.483(5) . ?
C19 C26 1.518(5) . ?
C20 C21 1.396(6) . ?
C20 C25 1.398(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.369(7) . ?
C23 H23 0.9500 . ?
C23 C24 1.383(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.392(6) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28 0.9500 . ?
C28 C29 1.359(5) . ?
C29 C30 1.406(5) . ?
C30 H30 0.9500 . ?
C30 C31 1.358(5) . ?
C31 C32 1.441(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
C26 O3 C27 108.0(3) . . ?
C1 N1 C10 126.4(3) . . ?
C9 N1 C1 111.4(3) . . ?
C9 N1 C10 122.2(3) . . ?
C28 N2 C17 119.0(3) . . ?
C28 N2 C32 124.4(3) . . ?
C32 N2 C17 116.6(3) . . ?
N1 C1 C7 109.5(3) . . ?
C2 C1 N1 128.8(3) . . ?
C2 C1 C7 121.7(3) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.8(3) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 100.1(3) . . ?
C3 C4 C6 120.7(4) . . ?
C6 C4 C5 139.0(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6 120.4 . . ?
C7 C6 C4 119.2(3) . . ?
C7 C6 H6 120.4 . . ?
C1 C7 C8 106.9(3) . . ?
C6 C7 C1 119.2(3) . . ?
C6 C7 C8 133.9(3) . . ?
C7 C8 C9 105.8(3) . . ?
C17 C8 C7 129.5(3) . . ?
C17 C8 C9 124.5(3) . . ?
O1 C9 N1 125.2(3) . . ?
O1 C9 C8 128.4(3) . . ?
N1 C9 C8 106.4(3) . . ?
N1 C10 H10A 109.3 . . ?
N1 C10 H10B 109.3 . . ?
N1 C10 C11 111.8(3) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C12 C11 C10 120.4(3) . . ?
C16 C11 C10 121.2(4) . . ?
C16 C11 C12 118.4(4) . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.7(4) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.9(4) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.7(4) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.3(4) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 121.0(4) . . ?
C15 C16 H16 119.5 . . ?
N2 C17 C18 116.5(3) . . ?
C8 C17 N2 119.0(3) . . ?
C8 C17 C18 124.4(3) . . ?
C17 C18 H18 115.9 . . ?
C19 C18 C17 128.2(3) . . ?
C19 C18 H18 115.9 . . ?
C18 C19 C20 118.8(3) . . ?
C18 C19 C26 127.7(3) . . ?
C20 C19 C26 113.1(3) . . ?
C21 C20 C19 120.7(3) . . ?
C21 C20 C25 118.9(3) . . ?
C25 C20 C19 120.4(3) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.8(4) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.4(4) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 120.5 . . ?
C22 C23 C24 119.0(4) . . ?
C24 C23 H23 120.5 . . ?
C23 C24 H24 119.5 . . ?
C23 C24 C25 121.0(4) . . ?
C25 C24 H24 119.5 . . ?
C20 C25 H25 120.1 . . ?
C24 C25 C20 119.7(4) . . ?
C24 C25 H25 120.1 . . ?
O3 C26 C19 109.5(3) . . ?
O3 C26 H26A 109.8 . . ?
O3 C26 H26B 109.8 . . ?
C19 C26 H26A 109.8 . . ?
C19 C26 H26B 109.8 . . ?
H26A C26 H26B 108.2 . . ?
O3 C27 H27A 109.5 . . ?
O3 C27 H27B 109.5 . . ?
O3 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N2 C28 H28 120.6 . . ?
C29 C28 N2 118.9(3) . . ?
C29 C28 H28 120.6 . . ?
C28 C29 Br1 119.0(3) . . ?
C28 C29 C30 121.1(3) . . ?
C30 C29 Br1 119.8(3) . . ?
C29 C30 H30 120.5 . . ?
C31 C30 C29 119.0(3) . . ?
C31 C30 H30 120.5 . . ?
C30 C31 Br 120.8(3) . . ?
C30 C31 C32 123.0(3) . . ?
C32 C31 Br 116.2(2) . . ?
O2 C32 N2 120.5(3) . . ?
O2 C32 C31 126.1(3) . . ?
N2 C32 C31 113.4(3) . . ?

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
Br C31 C32 O2 5.2(4) . . . . ?
Br C31 C32 N2 -176.4(2) . . . . ?
Br1 C29 C30 C31 -177.8(2) . . . . ?
N1 C1 C2 C3 -178.5(3) . . . . ?
N1 C1 C7 C6 -179.2(3) . . . . ?
N1 C1 C7 C8 0.8(4) . . . . ?
N1 C10 C11 C12 89.6(4) . . . . ?
N1 C10 C11 C16 -89.5(4) . . . . ?
N2 C17 C18 C19 -34.3(5) . . . . ?
N2 C28 C29 Br1 177.4(2) . . . . ?
N2 C28 C29 C30 0.5(5) . . . . ?
C1 N1 C9 O1 -179.3(3) . . . . ?
C1 N1 C9 C8 -0.3(4) . . . . ?
C1 N1 C10 C11 95.8(4) . . . . ?
C1 C2 C3 C4 -1.8(5) . . . . ?
C1 C7 C8 C9 -0.9(3) . . . . ?
C1 C7 C8 C17 174.5(3) . . . . ?
C2 C1 C7 C6 0.9(5) . . . . ?
C2 C1 C7 C8 -179.1(3) . . . . ?
C2 C3 C4 C5 -175.2(3) . . . . ?
C2 C3 C4 C6 0.0(6) . . . . ?
C3 C4 C6 C7 2.3(5) . . . . ?
C4 C6 C7 C1 -2.7(5) . . . . ?
C4 C6 C7 C8 177.3(3) . . . . ?
C5 C4 C6 C7 175.1(4) . . . . ?
C6 C7 C8 C9 179.1(4) . . . . ?
C6 C7 C8 C17 -5.5(6) . . . . ?
C7 C1 C2 C3 1.4(5) . . . . ?
C7 C8 C9 O1 179.7(3) . . . . ?
C7 C8 C9 N1 0.7(3) . . . . ?
C7 C8 C17 N2 175.4(3) . . . . ?
C7 C8 C17 C18 -8.8(6) . . . . ?
C8 C17 C18 C19 149.9(4) . . . . ?
C9 N1 C1 C2 179.6(3) . . . . ?
C9 N1 C1 C7 -0.3(4) . . . . ?
C9 N1 C10 C11 -83.5(4) . . . . ?
C9 C8 C17 N2 -10.0(5) . . . . ?
C9 C8 C17 C18 165.8(3) . . . . ?
C10 N1 C1 C2 0.2(6) . . . . ?
C10 N1 C1 C7 -179.7(3) . . . . ?
C10 N1 C9 O1 0.1(5) . . . . ?
C10 N1 C9 C8 179.1(3) . . . . ?
C10 C11 C12 C13 -178.0(3) . . . . ?
C10 C11 C16 C15 177.7(3) . . . . ?
C11 C12 C13 C14 0.9(6) . . . . ?
C12 C11 C16 C15 -1.4(6) . . . . ?
C12 C13 C14 C15 -2.4(6) . . . . ?
C13 C14 C15 C16 2.1(6) . . . . ?
C14 C15 C16 C11 -0.2(6) . . . . ?
C16 C11 C12 C13 1.0(6) . . . . ?
C17 N2 C28 C29 -178.1(3) . . . . ?
C17 N2 C32 O2 -5.7(4) . . . . ?
C17 N2 C32 C31 175.8(3) . . . . ?
C17 C8 C9 O1 4.0(6) . . . . ?
C17 C8 C9 N1 -174.9(3) . . . . ?
C17 C18 C19 C20 172.9(3) . . . . ?
C17 C18 C19 C26 1.1(6) . . . . ?
C18 C19 C20 C21 -52.5(5) . . . . ?
C18 C19 C20 C25 127.2(4) . . . . ?
C18 C19 C26 O3 -56.1(5) . . . . ?
C19 C20 C21 C22 179.1(4) . . . . ?
C19 C20 C25 C24 -177.6(3) . . . . ?
C20 C19 C26 O3 131.7(3) . . . . ?
C20 C21 C22 C23 -1.5(7) . . . . ?
C21 C20 C25 C24 2.2(5) . . . . ?
C21 C22 C23 C24 2.1(7) . . . . ?
C22 C23 C24 C25 -0.5(7) . . . . ?
C23 C24 C25 C20 -1.6(6) . . . . ?
C25 C20 C21 C22 -0.6(6) . . . . ?
C26 C19 C20 C21 120.4(4) . . . . ?
C26 C19 C20 C25 -59.8(4) . . . . ?
C27 O3 C26 C19 178.2(3) . . . . ?
C28 N2 C17 C8 -64.0(4) . . . . ?
C28 N2 C17 C18 120.0(3) . . . . ?
C28 N2 C32 O2 173.4(3) . . . . ?
C28 N2 C32 C31 -5.1(4) . . . . ?
C28 C29 C30 C31 -0.9(5) . . . . ?
C29 C30 C31 Br 179.2(2) . . . . ?
C29 C30 C31 C32 -1.8(5) . . . . ?
C30 C31 C32 O2 -173.9(3) . . . . ?
C30 C31 C32 N2 4.6(4) . . . . ?
C32 N2 C17 C8 115.2(3) . . . . ?
C32 N2 C17 C18 -60.9(4) . . . . ?
C32 N2 C28 C29 2.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.376
_oxdiff_exptl_absorpt_empirical_full_min 0.629
####################################################################### 
# 
# 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_zhangmch_220401_auto
_database_code_depnum_ccdc_archive 'CCDC 2218808'
loop_
_audit_author_name
_audit_author_address
'MC zhang'
;sysu
China
;
_audit_update_record             
;
2022-11-10 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;
_audit_creation_date             2022-04-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 N2 O2'
_chemical_formula_sum            'C30 H24 N2 O2'
_chemical_formula_weight         444.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.0303(6)
_cell_length_b                   11.8859(2)
_cell_length_c                   20.2655(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4583.9(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6479
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.1500
_cell_measurement_theta_min      4.3510
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16600
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.700
_diffrn_reflns_theta_min         4.363
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  30.00   0.50    0.50    --   45.81 -21.00  49.00  120
  2  ω   -118.00 -29.00   0.50    5.00    -- -100.00 144.00  82.00  178
  3  ω     92.00 147.00   0.50    5.00    --  104.88  21.00-144.00  110
  4  ω     98.00 174.00   0.50    5.00    --  104.88 104.00  16.00  152
  5  ω    -36.00   9.00   0.50    0.50    --  -45.81  38.00 -60.00   90
  6  ω   -112.00 -85.00   0.50    0.50    --  -45.81-125.00 150.00   54
  7  ω    -14.00  20.00   0.50    0.50    --   45.81 -19.00 -90.00   68
  8  ω    -69.00 -41.00   0.50    5.00    -- -100.00  61.00-120.00   56
  9  ω    -66.00 -39.00   0.50    5.00    -- -100.00  61.00 150.00   54
 10  ω     70.00 111.00   0.50    5.00    --  104.88-125.00 -30.00   82
 11  ω     81.00 106.00   0.50    5.00    --  104.88 -94.00-180.00   50
 12  ω     52.00  78.00   0.50    5.00    --  104.88 -94.00-180.00   52
 13  ω     32.00  65.00   0.50    5.00    --  104.88-125.00 -30.00   66
 14  ω     35.00  60.00   0.50    5.00    --  104.88 -61.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0646109000
_diffrn_orient_matrix_UB_12      -0.0249113000
_diffrn_orient_matrix_UB_13      0.0433397000
_diffrn_orient_matrix_UB_21      -0.0436770000
_diffrn_orient_matrix_UB_22      0.0254439000
_diffrn_orient_matrix_UB_23      0.0621997000
_diffrn_orient_matrix_UB_31      -0.0219754000
_diffrn_orient_matrix_UB_32      -0.1246763000
_diffrn_orient_matrix_UB_33      0.0041233000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3768
_reflns_number_total             4583
_reflns_odcompleteness_completeness 99.83
_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 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4583
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.046
_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)+(0.0632P)²+1.6393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1335
_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 Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C14(H14), C15(H15), C16(H16),
 C17(H17), C20(H20), C21(H21), C22(H22), C24(H24), C26(H26), C28(H28), C29(H29),
  C30(H30), C32(H32), C33(H33)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21264(8) 0.16181(9) 0.49805(6) 0.0280(3) Uani 1 1 d . . . . .
O2 O 0.17840(8) -0.00747(10) 0.60942(5) 0.0272(3) Uani 1 1 d . . . . .
N3 N 0.27231(9) -0.00577(10) 0.50157(6) 0.0203(3) Uani 1 1 d . . . . .
N4 N 0.07120(9) -0.08025(11) 0.57994(6) 0.0227(3) Uani 1 1 d . . . . .
C5 C 0.31459(12) -0.33915(16) 0.20839(9) 0.0310(4) Uani 1 1 d . . . . .
H5 H 0.318786 -0.393588 0.174291 0.037 Uiso 1 1 calc R U . . .
C6 C 0.06721(11) -0.15882(13) 0.40864(8) 0.0238(4) Uani 1 1 d . . . . .
H6 H 0.099057 -0.157693 0.372549 0.029 Uiso 1 1 calc R U . . .
C7 C 0.38102(12) 0.09648(14) 0.56672(8) 0.0292(4) Uani 1 1 d . . . . .
H7 H 0.418868 0.131847 0.589176 0.035 Uiso 1 1 calc R U . . .
C8 C -0.02862(11) -0.16118(13) 0.51493(8) 0.0253(4) Uani 1 1 d . . . . .
H8 H -0.060724 -0.162078 0.550827 0.030 Uiso 1 1 calc R U . . .
C9 C 0.15313(11) -0.07369(12) 0.49648(7) 0.0212(4) Uani 1 1 d . . . . .
C10 C 0.11169(11) -0.22225(15) 0.70390(8) 0.0278(4) Uani 1 1 d . . . . .
H10 H 0.150822 -0.172902 0.700796 0.033 Uiso 1 1 calc R U . . .
C11 C 0.03930(11) -0.12425(12) 0.52295(8) 0.0209(4) Uani 1 1 d . . . . .
C12 C 0.26467(11) 0.10930(13) 0.51682(8) 0.0228(4) Uani 1 1 d . . . . .
C13 C 0.29995(10) -0.17897(13) 0.30894(8) 0.0215(4) Uani 1 1 d . . . . .
C14 C 0.29924(11) -0.29398(14) 0.32355(8) 0.0234(4) Uani 1 1 d . . . . .
H14 H 0.293664 -0.318054 0.367944 0.028 Uiso 1 1 calc R U . . .
C15 C -0.00229(12) -0.36588(15) 0.71503(8) 0.0285(4) Uani 1 1 d . . . . .
H15 H -0.041586 -0.414649 0.719187 0.034 Uiso 1 1 calc R U . . .
C16 C 0.12016(12) -0.32794(16) 0.73160(9) 0.0317(4) Uani 1 1 d . . . . .
H16 H 0.164982 -0.350798 0.747298 0.038 Uiso 1 1 calc R U . . .
C17 C 0.33162(11) -0.06651(13) 0.51732(8) 0.0240(4) Uani 1 1 d . . . . .
H17 H 0.333872 -0.143998 0.506023 0.029 Uiso 1 1 calc R U . . .
C18 C 0.13895(11) -0.04590(12) 0.56780(7) 0.0221(4) Uani 1 1 d . . . . .
C19 C 0.33466(11) 0.00579(13) 0.36451(8) 0.0253(4) Uani 1 1 d . . . . .
H19A H 0.380539 -0.015270 0.382666 0.038 Uiso 1 1 calc R U . . .
H19B H 0.313361 0.064042 0.392285 0.038 Uiso 1 1 calc R U . . .
H19C H 0.340731 0.034808 0.319611 0.038 Uiso 1 1 calc R U . . .
C20 C 0.38660(12) -0.01832(14) 0.54845(9) 0.0286(4) Uani 1 1 d . . . . .
H20 H 0.427931 -0.060181 0.557861 0.034 Uiso 1 1 calc R U . . .
C21 C 0.32273(12) 0.15592(13) 0.55263(8) 0.0277(4) Uani 1 1 d . . . . .
H21 H 0.319954 0.231864 0.567008 0.033 Uiso 1 1 calc R U . . .
C22 C 0.06313(11) -0.40062(15) 0.73645(8) 0.0295(4) Uani 1 1 d . . . . .
H22 H 0.069117 -0.473822 0.754421 0.035 Uiso 1 1 calc R U . . .
C23 C 0.21700(11) -0.06366(12) 0.46748(7) 0.0210(4) Uani 1 1 d . . . . .
C24 C 0.23546(11) -0.11935(12) 0.40604(7) 0.0213(4) Uani 1 1 d . . . . .
H24 H 0.206567 -0.181476 0.394479 0.026 Uiso 1 1 calc R U . . .
C25 C 0.04663(11) -0.18786(13) 0.68066(7) 0.0229(4) Uani 1 1 d . . . . .
C26 C 0.30988(11) -0.14579(14) 0.24335(8) 0.0250(4) Uani 1 1 d . . . . .
H26 H 0.312218 -0.067999 0.232827 0.030 Uiso 1 1 calc R U . . .
C27 C 0.28752(10) -0.09600(13) 0.36295(8) 0.0208(4) Uani 1 1 d . . . . .
C28 C -0.04880(11) -0.19737(14) 0.45207(9) 0.0271(4) Uani 1 1 d . . . . .
H28 H -0.095596 -0.222348 0.444882 0.032 Uiso 1 1 calc R U . . .
C29 C 0.31637(11) -0.22547(15) 0.19329(9) 0.0290(4) Uani 1 1 d . . . . .
H29 H 0.322015 -0.201870 0.148815 0.035 Uiso 1 1 calc R U . . .
C30 C -0.01070(11) -0.25985(14) 0.68744(8) 0.0259(4) Uani 1 1 d . . . . .
H30 H -0.055861 -0.236203 0.673073 0.031 Uiso 1 1 calc R U . . .
C31 C 0.08859(11) -0.12198(12) 0.47084(8) 0.0210(4) Uani 1 1 d . . . . .
C32 C 0.30664(11) -0.37332(14) 0.27365(9) 0.0275(4) Uani 1 1 d . . . . .
H32 H 0.306264 -0.451219 0.284135 0.033 Uiso 1 1 calc R U . . .
C33 C -0.00134(12) -0.19728(14) 0.40000(9) 0.0275(4) Uani 1 1 d . . . . .
H33 H -0.015808 -0.223814 0.357923 0.033 Uiso 1 1 calc R U . . .
C34 C 0.03912(12) -0.07636(14) 0.64538(8) 0.0266(4) Uani 1 1 d . . . . .
H34A H -0.011338 -0.057493 0.641046 0.032 Uiso 1 1 calc R U . . .
H34B H 0.061848 -0.016540 0.671840 0.032 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
O1 C12 1.231(2) . ?
O2 C18 1.218(2) . ?
N3 C12 1.410(2) . ?
N3 C17 1.377(2) . ?
N3 C23 1.435(2) . ?
N4 C11 1.406(2) . ?
N4 C18 1.375(3) . ?
N4 C34 1.461(2) . ?
C5 H5 0.9500 . ?
C5 C29 1.386(3) . ?
C5 C32 1.392(3) . ?
C6 H6 0.9500 . ?
C6 C31 1.395(2) . ?
C6 C33 1.393(3) . ?
C7 H7 0.9500 . ?
C7 C20 1.418(2) . ?
C7 C21 1.346(3) . ?
C8 H8 0.9500 . ?
C8 C11 1.375(3) . ?
C8 C28 1.398(3) . ?
C9 C18 1.507(2) . ?
C9 C23 1.355(3) . ?
C9 C31 1.452(3) . ?
C10 H10 0.9500 . ?
C10 C16 1.385(3) . ?
C10 C25 1.386(3) . ?
C11 C31 1.413(2) . ?
C12 C21 1.433(3) . ?
C13 C14 1.399(2) . ?
C13 C26 1.399(2) . ?
C13 C27 1.492(2) . ?
C14 H14 0.9500 . ?
C14 C32 1.390(2) . ?
C15 H15 0.9500 . ?
C15 C22 1.382(3) . ?
C15 C30 1.388(2) . ?
C16 H16 0.9500 . ?
C16 C22 1.391(3) . ?
C17 H17 0.9500 . ?
C17 C20 1.349(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 C27 1.506(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.453(2) . ?
C24 H24 0.9500 . ?
C24 C27 1.349(3) . ?
C25 C30 1.393(3) . ?
C25 C34 1.513(2) . ?
C26 H26 0.9500 . ?
C26 C29 1.393(2) . ?
C28 H28 0.9500 . ?
C28 C33 1.389(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?

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
C12 N3 C23 119.69(15) . . ?
C17 N3 C12 122.84(16) . . ?
C17 N3 C23 117.47(13) . . ?
C11 N4 C34 125.26(16) . . ?
C18 N4 C11 111.62(14) . . ?
C18 N4 C34 123.03(15) . . ?
C29 C5 H5 120.1 . . ?
C29 C5 C32 119.80(16) . . ?
C32 C5 H5 120.1 . . ?
C31 C6 H6 120.3 . . ?
C33 C6 H6 120.3 . . ?
C33 C6 C31 119.32(17) . . ?
C20 C7 H7 119.6 . . ?
C21 C7 H7 119.6 . . ?
C21 C7 C20 120.77(18) . . ?
C11 C8 H8 121.2 . . ?
C11 C8 C28 117.66(17) . . ?
C28 C8 H8 121.2 . . ?
C23 C9 C18 123.85(17) . . ?
C23 C9 C31 129.66(15) . . ?
C31 C9 C18 106.17(16) . . ?
C16 C10 H10 119.7 . . ?
C16 C10 C25 120.59(19) . . ?
C25 C10 H10 119.7 . . ?
N4 C11 C31 108.69(16) . . ?
C8 C11 N4 128.46(16) . . ?
C8 C11 C31 122.82(15) . . ?
O1 C12 N3 120.47(17) . . ?
O1 C12 C21 125.50(15) . . ?
N3 C12 C21 113.99(16) . . ?
C14 C13 C26 118.55(15) . . ?
C14 C13 C27 119.28(14) . . ?
C26 C13 C27 122.14(14) . . ?
C13 C14 H14 119.7 . . ?
C32 C14 C13 120.53(16) . . ?
C32 C14 H14 119.7 . . ?
C22 C15 H15 119.9 . . ?
C22 C15 C30 120.13(18) . . ?
C30 C15 H15 119.9 . . ?
C10 C16 H16 120.0 . . ?
C10 C16 C22 120.1(2) . . ?
C22 C16 H16 120.0 . . ?
N3 C17 H17 119.3 . . ?
C20 C17 N3 121.42(15) . . ?
C20 C17 H17 119.3 . . ?
O2 C18 N4 124.44(15) . . ?
O2 C18 C9 129.50(18) . . ?
N4 C18 C9 105.93(15) . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C27 C19 H19A 109.5 . . ?
C27 C19 H19B 109.5 . . ?
C27 C19 H19C 109.5 . . ?
C7 C20 H20 120.9 . . ?
C17 C20 C7 118.20(19) . . ?
C17 C20 H20 120.9 . . ?
C7 C21 C12 122.67(15) . . ?
C7 C21 H21 118.7 . . ?
C12 C21 H21 118.7 . . ?
C15 C22 C16 119.69(17) . . ?
C15 C22 H22 120.2 . . ?
C16 C22 H22 120.2 . . ?
N3 C23 C24 116.98(17) . . ?
C9 C23 N3 119.43(14) . . ?
C9 C23 C24 123.24(16) . . ?
C23 C24 H24 115.2 . . ?
C27 C24 C23 129.66(16) . . ?
C27 C24 H24 115.2 . . ?
C10 C25 C30 118.99(16) . . ?
C10 C25 C34 120.22(17) . . ?
C30 C25 C34 120.72(18) . . ?
C13 C26 H26 119.6 . . ?
C29 C26 C13 120.80(16) . . ?
C29 C26 H26 119.6 . . ?
C13 C27 C19 116.86(15) . . ?
C24 C27 C13 117.08(15) . . ?
C24 C27 C19 126.06(15) . . ?
C8 C28 H28 119.6 . . ?
C33 C28 C8 120.89(19) . . ?
C33 C28 H28 119.6 . . ?
C5 C29 C26 119.98(16) . . ?
C5 C29 H29 120.0 . . ?
C26 C29 H29 120.0 . . ?
C15 C30 C25 120.47(19) . . ?
C15 C30 H30 119.8 . . ?
C25 C30 H30 119.8 . . ?
C6 C31 C9 133.97(17) . . ?
C6 C31 C11 118.41(18) . . ?
C11 C31 C9 107.56(14) . . ?
C5 C32 H32 119.9 . . ?
C14 C32 C5 120.29(16) . . ?
C14 C32 H32 119.9 . . ?
C6 C33 H33 119.5 . . ?
C28 C33 C6 120.90(17) . . ?
C28 C33 H33 119.5 . . ?
N4 C34 C25 111.22(13) . . ?
N4 C34 H34A 109.4 . . ?
N4 C34 H34B 109.4 . . ?
C25 C34 H34A 109.4 . . ?
C25 C34 H34B 109.4 . . ?
H34A C34 H34B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C12 C21 C7 -173.93(18) . . . . ?
N3 C12 C21 C7 3.9(3) . . . . ?
N3 C17 C20 C7 2.1(3) . . . . ?
N3 C23 C24 C27 -26.3(2) . . . . ?
N4 C11 C31 C6 -178.01(13) . . . . ?
N4 C11 C31 C9 -0.59(17) . . . . ?
C8 C11 C31 C6 0.0(2) . . . . ?
C8 C11 C31 C9 177.45(14) . . . . ?
C8 C28 C33 C6 -1.4(3) . . . . ?
C9 C23 C24 C27 160.56(17) . . . . ?
C10 C16 C22 C15 -1.6(3) . . . . ?
C10 C25 C30 C15 -2.1(2) . . . . ?
C10 C25 C34 N4 71.4(2) . . . . ?
C11 N4 C18 O2 -178.04(15) . . . . ?
C11 N4 C18 C9 -1.90(17) . . . . ?
C11 N4 C34 C25 82.0(2) . . . . ?
C11 C8 C28 C33 0.9(2) . . . . ?
C12 N3 C17 C20 -0.3(3) . . . . ?
C12 N3 C23 C9 -62.83(19) . . . . ?
C12 N3 C23 C24 123.74(16) . . . . ?
C13 C14 C32 C5 -0.2(3) . . . . ?
C13 C26 C29 C5 -1.4(3) . . . . ?
C14 C13 C26 C29 2.3(3) . . . . ?
C14 C13 C27 C19 136.58(18) . . . . ?
C14 C13 C27 C24 -43.0(3) . . . . ?
C16 C10 C25 C30 2.0(2) . . . . ?
C16 C10 C25 C34 -174.89(15) . . . . ?
C17 N3 C12 O1 175.32(16) . . . . ?
C17 N3 C12 C21 -2.6(2) . . . . ?
C17 N3 C23 C9 117.91(17) . . . . ?
C17 N3 C23 C24 -55.52(19) . . . . ?
C18 N4 C11 C8 -176.27(15) . . . . ?
C18 N4 C11 C31 1.63(17) . . . . ?
C18 N4 C34 C25 -94.32(19) . . . . ?
C18 C9 C23 N3 -11.3(2) . . . . ?
C18 C9 C23 C24 161.72(14) . . . . ?
C18 C9 C31 C6 176.31(17) . . . . ?
C18 C9 C31 C11 -0.53(16) . . . . ?
C20 C7 C21 C12 -2.3(3) . . . . ?
C21 C7 C20 C17 -0.8(3) . . . . ?
C22 C15 C30 C25 0.4(3) . . . . ?
C23 N3 C12 O1 -3.9(2) . . . . ?
C23 N3 C12 C21 178.19(14) . . . . ?
C23 N3 C17 C20 178.97(16) . . . . ?
C23 C9 C18 O2 3.2(3) . . . . ?
C23 C9 C18 N4 -172.65(14) . . . . ?
C23 C9 C31 C6 -10.0(3) . . . . ?
C23 C9 C31 C11 173.13(15) . . . . ?
C23 C24 C27 C13 171.17(17) . . . . ?
C23 C24 C27 C19 -8.4(3) . . . . ?
C25 C10 C16 C22 -0.1(3) . . . . ?
C26 C13 C14 C32 -1.5(3) . . . . ?
C26 C13 C27 C19 -45.8(3) . . . . ?
C26 C13 C27 C24 134.63(19) . . . . ?
C27 C13 C14 C32 176.29(18) . . . . ?
C27 C13 C26 C29 -175.38(19) . . . . ?
C28 C8 C11 N4 177.43(15) . . . . ?
C28 C8 C11 C31 -0.2(2) . . . . ?
C29 C5 C32 C14 1.1(3) . . . . ?
C30 C15 C22 C16 1.4(3) . . . . ?
C30 C25 C34 N4 -105.37(19) . . . . ?
C31 C6 C33 C28 1.2(2) . . . . ?
C31 C9 C18 O2 177.33(15) . . . . ?
C31 C9 C18 N4 1.47(16) . . . . ?
C31 C9 C23 N3 176.06(14) . . . . ?
C31 C9 C23 C24 -10.9(3) . . . . ?
C32 C5 C29 C26 -0.3(3) . . . . ?
C33 C6 C31 C9 -177.11(16) . . . . ?
C33 C6 C31 C11 -0.5(2) . . . . ?
C34 N4 C11 C8 7.0(3) . . . . ?
C34 N4 C11 C31 -175.06(14) . . . . ?
C34 N4 C18 O2 -1.3(2) . . . . ?
C34 N4 C18 C9 174.87(13) . . . . ?
C34 C25 C30 C15 174.72(15) . . . . ?

_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 3.745
_oxdiff_exptl_absorpt_empirical_full_min 0.175
####################################################################### 
# 
# 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_7241
_database_code_depnum_ccdc_archive 'CCDC 2248874'
loop_
_audit_author_name
_audit_author_address
'MC zhang'
;sysu
China
;
_audit_update_record             
;
2023-03-15 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;
_audit_creation_date             2023-03-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 N2 O4'
_chemical_formula_sum            'C24 H20 N2 O4'
_chemical_formula_weight         400.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   8.6150(3)
_cell_length_b                   9.0762(3)
_cell_length_c                   26.1585(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.231(3)
_cell_angle_gamma                90
_cell_volume                     2044.90(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6424
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.1930
_cell_measurement_theta_min      5.1330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12801
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.043
_diffrn_reflns_theta_max         67.043
_diffrn_reflns_theta_min         5.135
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00 -12.00   1.00    2.00    --  -40.45 125.00   0.00   27
  2  ω   -107.00 -21.00   1.00    2.00    --  -40.45 -38.00 -60.00   86
  3  ω   -115.00 -17.00   1.00    2.00    --  -40.45 -38.00-150.00   98
  4  ω    -85.00 -49.00   1.00    2.00    --  -40.45 125.00   0.00   36
  5  ω    -54.00 -12.00   1.00    2.00    --  -40.45 125.00  90.00   42
  6  ω     48.00  86.00   1.00    2.00    --   40.45-125.00 -90.00   38
  7  ω      9.00  35.00   1.00    2.00    --   40.45 -99.00  90.00   26
  8  ω     47.00  89.00   1.00    5.00    --  103.61-125.00 -90.00   42
  9  ω     21.00 101.00   1.00    5.00    --  103.61 -94.00  60.00   80
 10  ω    102.00 136.00   1.00    5.00    --  103.61 125.00 -30.00   34
 11  ω     54.00 126.00   1.00    5.00    --  103.61  15.00 -30.00   72
 12  ω    152.00 178.00   1.00    5.00    --  103.61  15.00 -30.00   26
 13  ω     77.00 113.00   1.00    5.00    --  103.61-125.00 -60.00   36
 14  ω     73.00 101.00   1.00    5.00    --  103.61 -94.00 -30.00   28
 15  ω     22.00  49.00   1.00    5.00    --  103.61 -94.00 -30.00   27
 16  ω     51.00 133.00   1.00    5.00    --  103.61 -61.00  60.00   82
 17  ω     71.00 100.00   1.00    5.00    --  103.61 -94.00 150.00   29
 18  ω    103.00 153.00   1.00    5.00    --  103.61  77.00 120.00   50
 19  ω     82.00 165.00   1.00    5.00    --  103.61  45.00  30.00   83
 20  ω     31.00 130.00   1.00    5.00    --  103.61 -61.00-120.00   99
 21  ω     39.00 113.00   1.00    5.00    --  103.61 -30.00   0.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1737532000
_diffrn_orient_matrix_UB_12      0.0073822000
_diffrn_orient_matrix_UB_13      0.0124614000
_diffrn_orient_matrix_UB_21      -0.0420646000
_diffrn_orient_matrix_UB_22      -0.0473142000
_diffrn_orient_matrix_UB_23      -0.0551389000
_diffrn_orient_matrix_UB_31      0.0043194000
_diffrn_orient_matrix_UB_32      -0.1628551000
_diffrn_orient_matrix_UB_33      0.0165980000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3148
_reflns_number_total             3644
_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 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3644
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0875P)²+0.4843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1518
_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. Restrained distances
 O19-C20 \\sim O19A-C20A
 with sigma of 0.02
 O22-C18 \\sim O22A-C18A
 with sigma of 0.02
 C17-C18 \\sim C17-C18A
 with sigma of 0.02
 C20-C21 \\sim C20A-C21A
 with sigma of 0.02
 O19-O22 \\sim O19A-O22A
 with sigma of 0.04
 O19-C17 \\sim O19A-C17
 with sigma of 0.04
 O19-C21 \\sim O19A-C21A
 with sigma of 0.04
 O22-C17 \\sim O22A-C17
 with sigma of 0.04
 C18-C20 \\sim C18A-C20A
 with sigma of 0.04
 C18A-C17 \\sim C18-C17
 with sigma of 0.02
 O22A-C18A \\sim O22-C18
 with sigma of 0.02
 O19-C18 \\sim O19A-C18A
 with sigma of 0.02
 O19A-C20A \\sim O19-C20
 with sigma of 0.02
 C21-C20 \\sim C21A-C20A
 with sigma of 0.02
3. Restrained planarity
 C17, C18A, O22A, O19A
 with sigma of 0.1
 C17, C18, O22, O19
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C20A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
2A
Uanis(C20A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 O22A, C18A, O19A, C20A, C21A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C18, O22, O19, C20, C21
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
6. Others
 Sof(O22A)=Sof(C18A)=Sof(O19A)=Sof(C20A)=Sof(H20C)=Sof(H20D)=Sof(C21A)=
 Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(1)
 Sof(O19)=Sof(O22)=Sof(C18)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)=
 Sof(H21B)=Sof(H21C)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C20(H20A,H20B), C20A(H20C,H20D)
7.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C8(H8), C5(H5), C12(H12), C7(H7), C16(H16), C6(H6), C28(H28),
 C27(H27), C26(H26), C15(H15), C14(H14), C13(H13)
7.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C21A(H21D,H21E,H21F)
;
_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
O23 O 0.18172(16) 0.10049(14) 0.49966(5) 0.0641(4) Uani 1 1 d . . . . .
O19 O 0.5244(3) 0.3836(3) 0.62963(8) 0.0596(6) Uani 0.856(5) 1 d D U P A 1
O30 O 0.19652(19) 0.26529(18) 0.64887(5) 0.0774(4) Uani 1 1 d . . . . .
N1 N 0.10266(17) 0.30074(16) 0.45272(5) 0.0522(4) Uani 1 1 d . . . . .
N24 N 0.35174(17) 0.18047(16) 0.58667(5) 0.0516(4) Uani 1 1 d . . . . .
O22 O 0.3633(4) 0.5652(3) 0.60388(12) 0.0898(10) Uani 0.856(5) 1 d D U P A 1
C3 C 0.27073(19) 0.35258(19) 0.52059(7) 0.0495(4) Uani 1 1 d . . . . .
C2 C 0.1837(2) 0.23227(19) 0.49130(6) 0.0497(4) Uani 1 1 d . . . . .
C9 C 0.13232(19) 0.45285(19) 0.45243(6) 0.0508(4) Uani 1 1 d . . . . .
C4 C 0.2382(2) 0.48912(19) 0.49206(7) 0.0512(4) Uani 1 1 d . . . . .
C29 C 0.2699(2) 0.1605(2) 0.63180(7) 0.0611(5) Uani 1 1 d . . . . .
C17 C 0.3432(2) 0.32561(19) 0.56551(7) 0.0518(4) Uani 1 1 d D . . . .
C11 C 0.0557(2) 0.1986(2) 0.36576(7) 0.0560(4) Uani 1 1 d . . . . .
C10 C -0.0073(2) 0.2251(2) 0.41829(7) 0.0568(4) Uani 1 1 d . . . . .
H10A H -0.1013 0.2835 0.4151 0.068 Uiso 1 1 calc R U . . .
H10B H -0.0348 0.1311 0.4333 0.068 Uiso 1 1 calc R U . . .
C25 C 0.4400(2) 0.0723(2) 0.56527(7) 0.0565(4) Uani 1 1 d . . . . .
H25 H 0.4929 0.0917 0.5354 0.068 Uiso 1 1 calc R U . . .
C8 C 0.0669(2) 0.5571(2) 0.42046(8) 0.0597(5) Uani 1 1 d . . . . .
H8 H -0.0034 0.5306 0.3946 0.072 Uiso 1 1 calc R U . . .
C5 C 0.2810(2) 0.6360(2) 0.49796(8) 0.0605(5) Uani 1 1 d . . . . .
H5 H 0.3532 0.6631 0.5232 0.073 Uiso 1 1 calc R U . . .
C12 C 0.1693(3) 0.0946(2) 0.35872(8) 0.0701(5) Uani 1 1 d . . . . .
H12 H 0.2078 0.0414 0.3866 0.084 Uiso 1 1 calc R U . . .
C18 C 0.4101(4) 0.4410(3) 0.60117(11) 0.0584(7) Uani 0.856(5) 1 d D U P A 1
C7 C 0.1093(2) 0.7029(2) 0.42800(9) 0.0661(5) Uani 1 1 d . . . . .
H7 H 0.0658 0.7756 0.4072 0.079 Uiso 1 1 calc R U . . .
C16 C -0.0006(3) 0.2757(3) 0.32351(8) 0.0714(6) Uani 1 1 d . . . . .
H16 H -0.0778 0.3462 0.3274 0.086 Uiso 1 1 calc R U . . .
C6 C 0.2150(2) 0.7417(2) 0.46591(9) 0.0667(5) Uani 1 1 d . . . . .
H6 H 0.2425 0.8401 0.4701 0.080 Uiso 1 1 calc R U . . .
C28 C 0.2819(3) 0.0159(3) 0.65303(8) 0.0736(6) Uani 1 1 d . . . . .
H28 H 0.2279 -0.0060 0.6825 0.088 Uiso 1 1 calc R U . . .
C27 C 0.3689(3) -0.0892(2) 0.63174(9) 0.0775(6) Uani 1 1 d . . . . .
H27 H 0.3750 -0.1818 0.6469 0.093 Uiso 1 1 calc R U . . .
C26 C 0.4510(3) -0.0616(2) 0.58692(9) 0.0683(5) Uani 1 1 d . . . . .
H26 H 0.5118 -0.1346 0.5725 0.082 Uiso 1 1 calc R U . . .
C15 C 0.0578(3) 0.2481(3) 0.27535(9) 0.0870(8) Uani 1 1 d . . . . .
H15 H 0.0199 0.3005 0.2472 0.104 Uiso 1 1 calc R U . . .
C20 C 0.5997(3) 0.4815(3) 0.66666(9) 0.0719(8) Uani 0.856(5) 1 d D U P A 1
H20A H 0.5226 0.5356 0.6856 0.086 Uiso 0.856(5) 1 calc R U P A 1
H20B H 0.6655 0.5517 0.6494 0.086 Uiso 0.856(5) 1 calc R U P A 1
C14 C 0.1705(4) 0.1445(4) 0.26917(9) 0.0942(8) Uani 1 1 d . . . . .
H14 H 0.2089 0.1257 0.2369 0.113 Uiso 1 1 calc R U . . .
C13 C 0.2268(4) 0.0682(3) 0.31071(10) 0.0922(8) Uani 1 1 d . . . . .
H13 H 0.3044 -0.0018 0.3066 0.111 Uiso 1 1 calc R U . . .
C21 C 0.6939(6) 0.3875(4) 0.70171(15) 0.1237(15) Uani 0.856(5) 1 d D U P A 1
H21A H 0.7579 0.3230 0.6821 0.186 Uiso 0.856(5) 1 calc R U P A 1
H21B H 0.6264 0.3299 0.7225 0.186 Uiso 0.856(5) 1 calc R U P A 1
H21C H 0.7586 0.4486 0.7232 0.186 Uiso 0.856(5) 1 calc R U P A 1
O22A O 0.441(2) 0.5683(17) 0.5892(7) 0.091(5) Uani 0.144(5) 1 d D U P A 2
C18A C 0.440(3) 0.436(2) 0.5941(8) 0.096(7) Uani 0.144(5) 1 d D U P A 2
O19A O 0.540(3) 0.384(3) 0.6288(9) 0.129(7) Uani 0.144(5) 1 d D U P A 2
C20A C 0.487(4) 0.386(3) 0.6801(9) 0.143(7) Uani 0.144(5) 1 d D U P A 2
H20C H 0.3746 0.3815 0.6791 0.172 Uiso 0.144(5) 1 calc R U P A 2
H20D H 0.5242 0.2971 0.6971 0.172 Uiso 0.144(5) 1 calc R U P A 2
C21A C 0.5320(17) 0.5065(19) 0.7098(6) 0.078(4) Uani 0.144(5) 1 d D U P A 2
H21D H 0.6120 0.5601 0.6929 0.117 Uiso 0.144(5) 1 calc R U P A 2
H21E H 0.5707 0.4729 0.7425 0.117 Uiso 0.144(5) 1 calc R U P A 2
H21F H 0.4442 0.5698 0.7146 0.117 Uiso 0.144(5) 1 calc R U P A 2


_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
O23 C2 1.216(2) . ?
O19 C18 1.328(3) . ?
O19 C20 1.457(3) . ?
O30 C29 1.231(2) . ?
N1 C2 1.364(2) . ?
N1 C9 1.404(2) . ?
N1 C10 1.464(2) . ?
N24 C29 1.400(2) . ?
N24 C17 1.430(2) . ?
N24 C25 1.369(2) . ?
O22 C18 1.200(3) . ?
C3 C2 1.522(2) . ?
C3 C4 1.470(2) . ?
C3 C17 1.341(3) . ?
C9 C4 1.405(2) . ?
C9 C8 1.375(3) . ?
C4 C5 1.391(3) . ?
C29 C28 1.428(3) . ?
C17 C18 1.508(3) . ?
C17 C18A 1.492(16) . ?
C11 C10 1.508(3) . ?
C11 C12 1.375(3) . ?
C11 C16 1.387(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C25 H25 0.9300 . ?
C25 C26 1.343(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.386(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.378(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.389(3) . ?
C6 H6 0.9300 . ?
C28 H28 0.9300 . ?
C28 C27 1.342(3) . ?
C27 H27 0.9300 . ?
C27 C26 1.404(3) . ?
C26 H26 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.363(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.482(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.369(4) . ?
C13 H13 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
O22A C18A 1.210(16) . ?
C18A O19A 1.325(17) . ?
O19A C20A 1.426(18) . ?
C20A H20C 0.9700 . ?
C20A H20D 0.9700 . ?
C20A C21A 1.394(18) . ?
C21A H21D 0.9600 . ?
C21A H21E 0.9600 . ?
C21A H21F 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
C18 O19 C20 116.6(2) . . ?
C2 N1 C9 111.20(14) . . ?
C2 N1 C10 123.74(15) . . ?
C9 N1 C10 124.98(15) . . ?
C29 N24 C17 115.03(15) . . ?
C25 N24 C29 123.09(17) . . ?
C25 N24 C17 121.81(15) . . ?
C4 C3 C2 105.23(14) . . ?
C17 C3 C2 121.68(16) . . ?
C17 C3 C4 132.72(16) . . ?
O23 C2 N1 124.90(15) . . ?
O23 C2 C3 128.58(16) . . ?
N1 C2 C3 106.51(14) . . ?
N1 C9 C4 109.98(15) . . ?
C8 C9 N1 127.40(16) . . ?
C8 C9 C4 122.58(17) . . ?
C9 C4 C3 106.89(15) . . ?
C5 C4 C3 134.78(17) . . ?
C5 C4 C9 118.21(17) . . ?
O30 C29 N24 118.52(19) . . ?
O30 C29 C28 127.1(2) . . ?
N24 C29 C28 114.42(18) . . ?
N24 C17 C18 112.61(17) . . ?
N24 C17 C18A 113.6(9) . . ?
C3 C17 N24 121.74(15) . . ?
C3 C17 C18 125.42(19) . . ?
C3 C17 C18A 124.1(9) . . ?
C12 C11 C10 120.17(17) . . ?
C12 C11 C16 118.52(19) . . ?
C16 C11 C10 121.30(19) . . ?
N1 C10 C11 113.24(14) . . ?
N1 C10 H10A 108.9 . . ?
N1 C10 H10B 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N24 C25 H25 119.6 . . ?
C26 C25 N24 120.77(19) . . ?
C26 C25 H25 119.6 . . ?
C9 C8 H8 121.1 . . ?
C9 C8 C7 117.84(19) . . ?
C7 C8 H8 121.1 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.44(19) . . ?
C6 C5 H5 120.3 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.7(2) . . ?
C13 C12 H12 119.6 . . ?
O19 C18 C17 110.1(2) . . ?
O22 C18 O19 125.5(2) . . ?
O22 C18 C17 124.4(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 C8 120.99(19) . . ?
C6 C7 H7 119.5 . . ?
C11 C16 H16 119.9 . . ?
C11 C16 C15 120.3(2) . . ?
C15 C16 H16 119.9 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 120.91(19) . . ?
C7 C6 H6 119.5 . . ?
C29 C28 H28 119.0 . . ?
C27 C28 C29 121.9(2) . . ?
C27 C28 H28 119.0 . . ?
C28 C27 H27 119.5 . . ?
C28 C27 C26 121.0(2) . . ?
C26 C27 H27 119.5 . . ?
C25 C26 C27 118.8(2) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 H26 120.6 . . ?
C16 C15 H15 119.9 . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.9 . . ?
O19 C20 H20A 110.3 . . ?
O19 C20 H20B 110.3 . . ?
O19 C20 C21 106.9(2) . . ?
H20A C20 H20B 108.6 . . ?
C21 C20 H20A 110.3 . . ?
C21 C20 H20B 110.3 . . ?
C15 C14 H14 120.1 . . ?
C15 C14 C13 119.7(2) . . ?
C13 C14 H14 120.1 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O22A C18A C17 128.2(18) . . ?
O22A C18A O19A 114.8(19) . . ?
O19A C18A C17 117.0(17) . . ?
C18A O19A C20A 115(2) . . ?
O19A C20A H20C 108.2 . . ?
O19A C20A H20D 108.2 . . ?
H20C C20A H20D 107.4 . . ?
C21A C20A O19A 116(2) . . ?
C21A C20A H20C 108.2 . . ?
C21A C20A H20D 108.2 . . ?
C20A C21A H21D 109.5 . . ?
C20A C21A H21E 109.5 . . ?
C20A C21A H21F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?

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
O30 C29 C28 C27 -178.3(2) . . . . ?
N1 C9 C4 C3 -3.05(19) . . . . ?
N1 C9 C4 C5 -179.61(15) . . . . ?
N1 C9 C8 C7 177.85(17) . . . . ?
N24 C29 C28 C27 1.9(3) . . . . ?
N24 C17 C18 O19 31.2(3) . . . . ?
N24 C17 C18 O22 -147.2(3) . . . . ?
N24 C17 C18A O22A -169.9(17) . . . . ?
N24 C17 C18A O19A 11.3(19) . . . . ?
N24 C25 C26 C27 0.7(3) . . . . ?
C3 C4 C5 C6 -173.42(19) . . . . ?
C3 C17 C18 O19 -154.2(2) . . . . ?
C3 C17 C18 O22 27.3(5) . . . . ?
C3 C17 C18A O22A 18(3) . . . . ?
C3 C17 C18A O19A -160.4(14) . . . . ?
C2 N1 C9 C4 0.40(19) . . . . ?
C2 N1 C9 C8 -177.30(17) . . . . ?
C2 N1 C10 C11 -104.70(19) . . . . ?
C2 C3 C4 C9 4.27(18) . . . . ?
C2 C3 C4 C5 179.99(19) . . . . ?
C2 C3 C17 N24 4.3(3) . . . . ?
C2 C3 C17 C18 -169.7(2) . . . . ?
C2 C3 C17 C18A 175.3(11) . . . . ?
C9 N1 C2 O23 -178.54(17) . . . . ?
C9 N1 C2 C3 2.34(18) . . . . ?
C9 N1 C10 C11 79.0(2) . . . . ?
C9 C4 C5 C6 1.9(3) . . . . ?
C9 C8 C7 C6 0.8(3) . . . . ?
C4 C3 C2 O23 176.87(18) . . . . ?
C4 C3 C2 N1 -4.06(17) . . . . ?
C4 C3 C17 N24 176.21(17) . . . . ?
C4 C3 C17 C18 2.2(4) . . . . ?
C4 C3 C17 C18A -12.8(11) . . . . ?
C4 C9 C8 C7 0.4(3) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C29 N24 C17 C3 -113.45(19) . . . . ?
C29 N24 C17 C18 61.3(2) . . . . ?
C29 N24 C17 C18A 74.7(10) . . . . ?
C29 N24 C25 C26 0.6(3) . . . . ?
C29 C28 C27 C26 -0.8(3) . . . . ?
C17 N24 C29 O30 1.3(2) . . . . ?
C17 N24 C29 C28 -178.83(16) . . . . ?
C17 N24 C25 C26 177.40(16) . . . . ?
C17 C3 C2 O23 -9.3(3) . . . . ?
C17 C3 C2 N1 169.76(16) . . . . ?
C17 C3 C4 C9 -168.58(19) . . . . ?
C17 C3 C4 C5 7.1(3) . . . . ?
C17 C18A O19A C20A -97(2) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C11 C16 C15 C14 0.3(4) . . . . ?
C10 N1 C2 O23 4.7(3) . . . . ?
C10 N1 C2 C3 -174.41(15) . . . . ?
C10 N1 C9 C4 177.11(15) . . . . ?
C10 N1 C9 C8 -0.6(3) . . . . ?
C10 C11 C12 C13 179.3(2) . . . . ?
C10 C11 C16 C15 -179.14(19) . . . . ?
C25 N24 C29 O30 178.30(17) . . . . ?
C25 N24 C29 C28 -1.9(2) . . . . ?
C25 N24 C17 C3 69.6(2) . . . . ?
C25 N24 C17 C18 -115.7(2) . . . . ?
C25 N24 C17 C18A -102.3(10) . . . . ?
C8 C9 C4 C3 174.78(16) . . . . ?
C8 C9 C4 C5 -1.8(3) . . . . ?
C8 C7 C6 C5 -0.6(3) . . . . ?
C12 C11 C10 N1 71.9(2) . . . . ?
C12 C11 C16 C15 -0.3(3) . . . . ?
C18 O19 C20 C21 166.6(3) . . . . ?
C16 C11 C10 N1 -109.3(2) . . . . ?
C16 C11 C12 C13 0.5(3) . . . . ?
C16 C15 C14 C13 -0.4(4) . . . . ?
C28 C27 C26 C25 -0.6(3) . . . . ?
C15 C14 C13 C12 0.6(4) . . . . ?
C20 O19 C18 O22 -0.8(5) . . . . ?
C20 O19 C18 C17 -179.2(3) . . . . ?
O22A C18A O19A C20A 84(3) . . . . ?
C18A O19A C20A C21A -96(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 1.454
_oxdiff_exptl_absorpt_empirical_full_min 0.558
