# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_cxy1850_0m
_database_code_depnum_ccdc_archive 'CCDC 2294530'
loop_
_audit_author_name
_audit_author_address
'Pengfei Li'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2023-09-12 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_audit_creation_date             2021-12-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H19 N O2'
_chemical_formula_sum            'C27 H19 N O2'
_chemical_formula_weight         389.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   8.0198(3)
_cell_length_b                   9.4799(4)
_cell_length_c                   13.7043(6)
_cell_angle_alpha                103.446(2)
_cell_angle_beta                 97.519(2)
_cell_angle_gamma                102.443(2)
_cell_volume                     971.41(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7787
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0801 before and 0.0549 after correction.
The Ratio of minimum to maximum transmission is 0.9586.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18544
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         2.284
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3334
_reflns_number_total             4454
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4454
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.038
_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)+(0.0506P)²+0.6448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1274
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.73922(17) 0.86669(14) 0.42618(10) 0.0232(3) Uani 1 1 d . . . . .
O2 O 0.17169(15) 0.40562(13) 0.05727(9) 0.0172(3) Uani 1 1 d . . . . .
N1 N 0.41685(19) 0.48461(16) 0.18532(10) 0.0158(3) Uani 1 1 d . . . . .
C1 C 1.0326(2) 0.6375(2) 0.66860(13) 0.0226(4) Uani 1 1 d . . . . .
H1 H 1.096839 0.617482 0.724860 0.027 Uiso 1 1 calc R U . . .
C2 C 1.0795(2) 0.7765(2) 0.64975(14) 0.0228(4) Uani 1 1 d . . . . .
H2 H 1.176999 0.850992 0.692412 0.027 Uiso 1 1 calc R U . . .
C3 C 0.9845(2) 0.8073(2) 0.56873(13) 0.0182(4) Uani 1 1 d . . . . .
H3 H 1.016903 0.902761 0.555810 0.022 Uiso 1 1 calc R U . . .
C4 C 0.8414(2) 0.6979(2) 0.50633(12) 0.0162(4) Uani 1 1 d . . . . .
C5 C 0.7368(2) 0.7357(2) 0.42240(13) 0.0178(4) Uani 1 1 d . . . . .
C6 C 0.6384(2) 0.6105(2) 0.33438(13) 0.0187(4) Uani 1 1 d . . . . .
H6 H 0.684141 0.525120 0.319204 0.022 Uiso 1 1 calc R U . . .
C7 C 0.4901(2) 0.60515(18) 0.27324(12) 0.0153(3) Uani 1 1 d . . . . .
C8 C 0.5058(2) 0.3720(2) 0.14855(13) 0.0179(4) Uani 1 1 d . . . . .
C9 C 0.6412(2) 0.41295(19) 0.09483(13) 0.0171(4) Uani 1 1 d . . . . .
H9 H 0.663725 0.507506 0.079959 0.020 Uiso 1 1 calc R U . . .
C10 C 0.7379(2) 0.3145(2) 0.06514(13) 0.0195(4) Uani 1 1 d . . . . .
H10 H 0.829453 0.341320 0.030113 0.023 Uiso 1 1 calc R U . . .
C11 C 0.7036(2) 0.17257(19) 0.08589(13) 0.0180(4) Uani 1 1 d . . . . .
C12 C 0.8057(2) 0.0698(2) 0.05701(13) 0.0208(4) Uani 1 1 d . . . . .
H12 H 0.900290 0.096933 0.024190 0.025 Uiso 1 1 calc R U . . .
C13 C 0.7687(2) -0.0679(2) 0.07617(13) 0.0210(4) Uani 1 1 d . . . . .
H13 H 0.836473 -0.136464 0.056063 0.025 Uiso 1 1 calc R U . . .
C14 C 0.3649(2) 0.69925(18) 0.27996(12) 0.0137(3) Uani 1 1 d . . . . .
C15 C 0.2265(2) 0.63232(18) 0.19767(12) 0.0132(3) Uani 1 1 d . . . . .
C16 C 0.2589(2) 0.49454(18) 0.13530(12) 0.0143(3) Uani 1 1 d . . . . .
C17 C 0.4642(2) 0.2362(2) 0.16940(13) 0.0179(4) Uani 1 1 d . . . . .
C18 C 0.5644(2) 0.1307(2) 0.13648(13) 0.0180(4) Uani 1 1 d . . . . .
C19 C 0.6309(2) -0.1072(2) 0.12537(14) 0.0222(4) Uani 1 1 d . . . . .
H19 H 0.606300 -0.202680 0.138789 0.027 Uiso 1 1 calc R U . . .
C20 C 0.5314(2) -0.0117(2) 0.15441(14) 0.0219(4) Uani 1 1 d . . . . .
H20 H 0.438002 -0.041721 0.187368 0.026 Uiso 1 1 calc R U . . .
C21 C 0.3216(2) 0.1958(2) 0.22524(15) 0.0229(4) Uani 1 1 d . . . . .
H21A H 0.275399 0.283004 0.248178 0.034 Uiso 1 1 calc R U . . .
H21B H 0.366964 0.164882 0.284623 0.034 Uiso 1 1 calc R U . . .
H21C H 0.228508 0.113070 0.179680 0.034 Uiso 1 1 calc R U . . .
C22 C 0.0820(2) 0.68855(19) 0.18443(13) 0.0171(4) Uani 1 1 d . . . . .
H22 H -0.009341 0.643436 0.126660 0.020 Uiso 1 1 calc R U . . .
C23 C 0.0763(2) 0.8140(2) 0.25937(14) 0.0204(4) Uani 1 1 d . . . . .
H23 H -0.021591 0.854993 0.253318 0.024 Uiso 1 1 calc R U . . .
C24 C 0.2120(2) 0.8802(2) 0.34297(13) 0.0198(4) Uani 1 1 d . . . . .
H24 H 0.203991 0.964488 0.393770 0.024 Uiso 1 1 calc R U . . .
C25 C 0.3591(2) 0.82569(19) 0.35382(13) 0.0168(4) Uani 1 1 d . . . . .
H25 H 0.452803 0.873363 0.410010 0.020 Uiso 1 1 calc R U . . .
C26 C 0.7965(2) 0.5574(2) 0.52485(13) 0.0178(4) Uani 1 1 d . . . . .
H26 H 0.700064 0.481969 0.481963 0.021 Uiso 1 1 calc R U . . .
C27 C 0.8928(2) 0.5279(2) 0.60592(14) 0.0211(4) Uani 1 1 d . . . . .
H27 H 0.862413 0.432037 0.618383 0.025 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 C5 1.227(2) . ?
O2 C16 1.214(2) . ?
N1 C7 1.410(2) . ?
N1 C8 1.441(2) . ?
N1 C16 1.392(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.383(3) . ?
C1 C27 1.381(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(2) . ?
C4 C5 1.492(2) . ?
C4 C26 1.393(3) . ?
C5 C6 1.472(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.347(2) . ?
C7 C14 1.477(2) . ?
C8 C9 1.426(2) . ?
C8 C17 1.364(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.362(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.416(2) . ?
C11 C12 1.424(2) . ?
C11 C18 1.423(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.369(3) . ?
C13 H13 0.9500 . ?
C13 C19 1.396(3) . ?
C14 C15 1.394(2) . ?
C14 C25 1.391(2) . ?
C15 C16 1.480(2) . ?
C15 C22 1.384(2) . ?
C17 C18 1.442(2) . ?
C17 C21 1.489(2) . ?
C18 C20 1.404(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.357(3) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22 0.9500 . ?
C22 C23 1.393(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.391(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.390(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.386(3) . ?
C27 H27 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C8 122.45(14) . . ?
C16 N1 C7 112.59(13) . . ?
C16 N1 C8 124.77(14) . . ?
C2 C1 H1 119.9 . . ?
C27 C1 H1 119.9 . . ?
C27 C1 C2 120.22(17) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.18(17) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.79(17) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 118.84(16) . . ?
C26 C4 C3 119.71(16) . . ?
C26 C4 C5 121.43(16) . . ?
O1 C5 C4 120.50(16) . . ?
O1 C5 C6 122.29(16) . . ?
C6 C5 C4 117.16(15) . . ?
C5 C6 H6 116.8 . . ?
C7 C6 C5 126.41(16) . . ?
C7 C6 H6 116.8 . . ?
N1 C7 C14 105.37(14) . . ?
C6 C7 N1 121.00(15) . . ?
C6 C7 C14 133.45(15) . . ?
C9 C8 N1 116.75(15) . . ?
C17 C8 N1 120.07(16) . . ?
C17 C8 C9 123.12(16) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.01(16) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.77(17) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 121.33(17) . . ?
C10 C11 C18 119.79(16) . . ?
C18 C11 C12 118.88(16) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.47(17) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C19 119.77(16) . . ?
C19 C13 H13 120.1 . . ?
C15 C14 C7 107.90(14) . . ?
C25 C14 C7 132.01(15) . . ?
C25 C14 C15 119.87(15) . . ?
C14 C15 C16 109.05(14) . . ?
C22 C15 C14 122.53(15) . . ?
C22 C15 C16 128.35(16) . . ?
O2 C16 N1 125.14(15) . . ?
O2 C16 C15 129.78(16) . . ?
N1 C16 C15 105.08(13) . . ?
C8 C17 C18 117.95(16) . . ?
C8 C17 C21 122.08(16) . . ?
C18 C17 C21 119.97(16) . . ?
C11 C18 C17 119.31(16) . . ?
C20 C18 C11 118.55(16) . . ?
C20 C18 C17 122.13(17) . . ?
C13 C19 H19 119.3 . . ?
C20 C19 C13 121.34(18) . . ?
C20 C19 H19 119.3 . . ?
C18 C20 H20 119.5 . . ?
C19 C20 C18 120.99(17) . . ?
C19 C20 H20 119.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C15 C22 H22 121.4 . . ?
C15 C22 C23 117.21(16) . . ?
C23 C22 H22 121.4 . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.82(16) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.48(16) . . ?
C25 C24 H24 119.3 . . ?
C14 C25 H25 121.0 . . ?
C24 C25 C14 118.04(16) . . ?
C24 C25 H25 121.0 . . ?
C4 C26 H26 120.0 . . ?
C27 C26 C4 119.92(17) . . ?
C27 C26 H26 120.0 . . ?
C1 C27 C26 120.17(18) . . ?
C1 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C5 C6 C7 -30.8(3) . . . . ?
N1 C7 C14 C15 -0.12(18) . . . . ?
N1 C7 C14 C25 174.27(18) . . . . ?
N1 C8 C9 C10 175.17(15) . . . . ?
N1 C8 C17 C18 -176.15(14) . . . . ?
N1 C8 C17 C21 3.2(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C1 C27 C26 -1.2(3) . . . . ?
C2 C3 C4 C5 177.44(15) . . . . ?
C2 C3 C4 C26 -1.0(2) . . . . ?
C3 C4 C5 O1 -22.4(2) . . . . ?
C3 C4 C5 C6 155.06(16) . . . . ?
C3 C4 C26 C27 0.9(2) . . . . ?
C4 C5 C6 C7 151.81(18) . . . . ?
C4 C26 C27 C1 0.2(2) . . . . ?
C5 C4 C26 C27 -177.55(15) . . . . ?
C5 C6 C7 N1 173.89(16) . . . . ?
C5 C6 C7 C14 -11.7(3) . . . . ?
C6 C7 C14 C15 -175.18(19) . . . . ?
C6 C7 C14 C25 -0.8(3) . . . . ?
C7 N1 C8 C9 -77.2(2) . . . . ?
C7 N1 C8 C17 100.1(2) . . . . ?
C7 N1 C16 O2 179.03(16) . . . . ?
C7 N1 C16 C15 -1.02(19) . . . . ?
C7 C14 C15 C16 -0.49(18) . . . . ?
C7 C14 C15 C22 176.61(16) . . . . ?
C7 C14 C25 C24 -173.15(17) . . . . ?
C8 N1 C7 C6 -8.2(3) . . . . ?
C8 N1 C7 C14 175.95(15) . . . . ?
C8 N1 C16 O2 3.9(3) . . . . ?
C8 N1 C16 C15 -176.10(15) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C8 C17 C18 C11 1.2(2) . . . . ?
C8 C17 C18 C20 179.99(16) . . . . ?
C9 C8 C17 C18 0.9(3) . . . . ?
C9 C8 C17 C21 -179.72(16) . . . . ?
C9 C10 C11 C12 -178.80(16) . . . . ?
C9 C10 C11 C18 1.3(3) . . . . ?
C10 C11 C12 C13 -178.88(16) . . . . ?
C10 C11 C18 C17 -2.3(2) . . . . ?
C10 C11 C18 C20 178.86(16) . . . . ?
C11 C12 C13 C19 -0.7(3) . . . . ?
C11 C18 C20 C19 0.8(3) . . . . ?
C12 C11 C18 C17 177.75(15) . . . . ?
C12 C11 C18 C20 -1.1(2) . . . . ?
C12 C13 C19 C20 0.4(3) . . . . ?
C13 C19 C20 C18 -0.4(3) . . . . ?
C14 C15 C16 O2 -179.14(17) . . . . ?
C14 C15 C16 N1 0.91(18) . . . . ?
C14 C15 C22 C23 -2.1(3) . . . . ?
C15 C14 C25 C24 0.7(2) . . . . ?
C15 C22 C23 C24 0.8(3) . . . . ?
C16 N1 C7 C6 176.55(16) . . . . ?
C16 N1 C7 C14 0.73(19) . . . . ?
C16 N1 C8 C9 97.4(2) . . . . ?
C16 N1 C8 C17 -85.3(2) . . . . ?
C16 C15 C22 C23 174.36(17) . . . . ?
C17 C8 C9 C10 -2.0(3) . . . . ?
C17 C18 C20 C19 -178.02(16) . . . . ?
C18 C11 C12 C13 1.0(3) . . . . ?
C21 C17 C18 C11 -178.14(16) . . . . ?
C21 C17 C18 C20 0.6(3) . . . . ?
C22 C15 C16 O2 4.0(3) . . . . ?
C22 C15 C16 N1 -175.97(17) . . . . ?
C22 C23 C24 C25 1.3(3) . . . . ?
C23 C24 C25 C14 -2.0(3) . . . . ?
C25 C14 C15 C16 -175.68(15) . . . . ?
C25 C14 C15 C22 1.4(3) . . . . ?
C26 C4 C5 O1 156.08(16) . . . . ?
C26 C4 C5 C6 -26.5(2) . . . . ?
C27 C1 C2 C3 1.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cxy1959_0m
_database_code_depnum_ccdc_archive 'CCDC 2294537'
loop_
_audit_author_name
_audit_author_address
'Pengfei Li'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2023-09-12 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_audit_creation_date             2022-07-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H19 N O2, C1.5 H3 O0.5'
_chemical_formula_sum            'C28.50 H22 N O2.50'
_chemical_formula_weight         418.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.218(2)
_cell_length_b                   10.8756(7)
_cell_length_c                   17.0557(12)
_cell_angle_alpha                90
_cell_angle_beta                 124.150(2)
_cell_angle_gamma                90
_cell_volume                     4331.7(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8495
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1525 before and 0.0681 after correction.
The Ratio of minimum to maximum transmission is 0.9194.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23405
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_min         2.222
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3496
_reflns_number_total             4998
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2014'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4998
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.025
_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)+(0.0508P)²+3.6210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1219
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C24(H24), C23(H23), C14(H14), C26(H26), C17(H17), C27(H27), C5(H5),
 C20(H20), C25(H25), C8(H8), C6(H6), C7(H7), C19(H19), C18(H18)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.49824(5) 1.05653(10) 0.60282(8) 0.0193(3) Uani 1 1 d . . . . .
O2 O 0.24870(5) 0.59514(10) 0.30357(8) 0.0190(3) Uani 1 1 d . . . . .
N1 N 0.45091(6) 0.89579(12) 0.49851(10) 0.0173(3) Uani 1 1 d . . . . .
H1 H 0.468349 0.899549 0.469026 0.021 Uiso 1 1 d R U . . .
C22 C 0.37960(7) 0.50580(14) 0.37143(12) 0.0148(3) Uani 1 1 d . . . . .
C12 C 0.25377(7) 0.60465(14) 0.23706(12) 0.0146(3) Uani 1 1 d . . . . .
C15 C 0.27063(7) 0.60007(14) 0.08414(11) 0.0160(4) Uani 1 1 d . . . . .
C1 C 0.46282(7) 0.97224(14) 0.57107(11) 0.0163(4) Uani 1 1 d . . . . .
C3 C 0.39039(7) 0.83756(15) 0.54152(11) 0.0162(4) Uani 1 1 d . . . . .
C9 C 0.38682(7) 0.72342(15) 0.41166(12) 0.0167(4) Uani 1 1 d . . . . .
C4 C 0.42416(7) 0.93450(14) 0.59965(11) 0.0160(3) Uani 1 1 d . . . . .
C13 C 0.20848(7) 0.56856(14) 0.14081(11) 0.0161(4) Uani 1 1 d . . . . .
H13 H 0.172261 0.544797 0.127492 0.019 Uiso 1 1 calc R U . . .
C2 C 0.40742(7) 0.81005(14) 0.47620(11) 0.0160(4) Uani 1 1 d . . . . .
C24 C 0.36702(7) 0.28987(15) 0.33246(12) 0.0180(4) Uani 1 1 d . . . . .
H24 H 0.345801 0.225769 0.288507 0.022 Uiso 1 1 calc R U . . .
C23 C 0.34955(7) 0.41082(14) 0.30719(12) 0.0150(3) Uani 1 1 d . . . . .
H23 H 0.316917 0.429106 0.245734 0.018 Uiso 1 1 calc R U . . .
C10 C 0.35993(7) 0.63611(14) 0.34881(11) 0.0146(3) Uani 1 1 d . . . . .
C16 C 0.31597(7) 0.64439(14) 0.17250(12) 0.0153(3) Uani 1 1 d . . . . .
C11 C 0.30667(7) 0.66815(14) 0.25074(11) 0.0143(3) Uani 1 1 d . . . . .
C14 C 0.21670(7) 0.56811(14) 0.07080(12) 0.0179(4) Uani 1 1 d . . . . .
H14 H 0.185516 0.545632 0.009068 0.021 Uiso 1 1 calc R U . . .
C26 C 0.44580(7) 0.35514(16) 0.48513(12) 0.0208(4) Uani 1 1 d . . . . .
H26 H 0.479050 0.336434 0.545802 0.025 Uiso 1 1 calc R U . . .
C17 C 0.36732(7) 0.67531(16) 0.18382(12) 0.0211(4) Uani 1 1 d . . . . .
H17 H 0.398183 0.706052 0.243023 0.025 Uiso 1 1 calc R U . . .
C21 C 0.29153(7) 0.80650(14) 0.24520(12) 0.0178(4) Uani 1 1 d . . . . .
H21A H 0.256422 0.824229 0.183222 0.027 Uiso 1 1 calc R U . . .
H21B H 0.322986 0.856497 0.253674 0.027 Uiso 1 1 calc R U . . .
H21C H 0.285631 0.826111 0.295222 0.027 Uiso 1 1 calc R U . . .
C27 C 0.42803(7) 0.47585(15) 0.46068(12) 0.0183(4) Uani 1 1 d . . . . .
H27 H 0.449082 0.539447 0.505266 0.022 Uiso 1 1 calc R U . . .
C5 C 0.41745(7) 0.98187(15) 0.66849(12) 0.0196(4) Uani 1 1 d . . . . .
H5 H 0.440905 1.047027 0.708853 0.023 Uiso 1 1 calc R U . . .
C20 C 0.27825(8) 0.58610(15) 0.01047(12) 0.0211(4) Uani 1 1 d . . . . .
H20 H 0.247763 0.555036 -0.048956 0.025 Uiso 1 1 calc R U . . .
C25 C 0.41498(7) 0.26148(15) 0.42091(12) 0.0203(4) Uani 1 1 d . . . . .
H25 H 0.426759 0.178363 0.437615 0.024 Uiso 1 1 calc R U . . .
C8 C 0.34816(7) 0.78592(15) 0.54923(12) 0.0194(4) Uani 1 1 d . . . . .
H8 H 0.325115 0.719878 0.509556 0.023 Uiso 1 1 calc R U . . .
C6 C 0.37532(8) 0.93053(16) 0.67604(12) 0.0223(4) Uani 1 1 d . . . . .
H6 H 0.369665 0.961297 0.722333 0.027 Uiso 1 1 calc R U . . .
C7 C 0.34091(7) 0.83436(16) 0.61699(12) 0.0221(4) Uani 1 1 d . . . . .
H7 H 0.312040 0.801628 0.623420 0.026 Uiso 1 1 calc R U . . .
C19 C 0.32949(8) 0.61683(17) 0.02293(13) 0.0251(4) Uani 1 1 d . . . . .
H19 H 0.334279 0.607269 -0.027596 0.030 Uiso 1 1 calc R U . . .
C18 C 0.37394(8) 0.66180(18) 0.10982(13) 0.0261(4) Uani 1 1 d . . . . .
H18 H 0.409235 0.683526 0.118626 0.031 Uiso 1 1 calc R U . . .
O3 O 0.500000 0.5587(2) 0.250000 0.0791(10) Uani 1 2 d S T P . .
C28 C 0.500000 0.4480(3) 0.250000 0.0334(7) Uani 1 2 d S T P . .
C29 C 0.47212(10) 0.3751(2) 0.28741(16) 0.0476(6) Uani 1 1 d . . . . .
H29A H 0.457195 0.430941 0.313769 0.071 Uiso 1 1 calc R U . . .
H29B H 0.500266 0.319490 0.337164 0.071 Uiso 1 1 calc R U . . .
H29C H 0.440551 0.327008 0.235919 0.071 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 C1 1.2350(19) . ?
O2 C12 1.2248(19) . ?
N1 H1 0.8800 . ?
N1 C1 1.367(2) . ?
N1 C2 1.413(2) . ?
C22 C23 1.394(2) . ?
C22 C10 1.492(2) . ?
C22 C27 1.398(2) . ?
C12 C13 1.458(2) . ?
C12 C11 1.539(2) . ?
C15 C16 1.406(2) . ?
C15 C14 1.449(2) . ?
C15 C20 1.397(2) . ?
C1 C4 1.481(2) . ?
C3 C4 1.393(2) . ?
C3 C2 1.471(2) . ?
C3 C8 1.389(2) . ?
C9 C2 1.311(2) . ?
C9 C10 1.309(2) . ?
C4 C5 1.389(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.338(2) . ?
C24 H24 0.9500 . ?
C24 C23 1.386(2) . ?
C24 C25 1.382(2) . ?
C23 H23 0.9500 . ?
C10 C11 1.535(2) . ?
C16 C11 1.520(2) . ?
C16 C17 1.391(2) . ?
C11 C21 1.552(2) . ?
C14 H14 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.383(2) . ?
C26 C25 1.387(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C27 H27 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.383(2) . ?
C20 H20 0.9500 . ?
C20 C19 1.379(3) . ?
C25 H25 0.9500 . ?
C8 H8 0.9500 . ?
C8 C7 1.386(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.398(2) . ?
C7 H7 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.386(3) . ?
C18 H18 0.9500 . ?
O3 C28 1.204(3) . ?
C28 C29 1.489(3) . ?
C28 C29 1.489(3) 2_655 ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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
C1 N1 H1 123.8 . . ?
C1 N1 C2 112.34(14) . . ?
C2 N1 H1 123.8 . . ?
C23 C22 C10 121.80(14) . . ?
C23 C22 C27 118.32(15) . . ?
C27 C22 C10 119.82(14) . . ?
O2 C12 C13 122.39(15) . . ?
O2 C12 C11 120.34(14) . . ?
C13 C12 C11 116.99(14) . . ?
C16 C15 C14 119.62(15) . . ?
C20 C15 C16 119.64(15) . . ?
C20 C15 C14 120.74(15) . . ?
O1 C1 N1 125.14(16) . . ?
O1 C1 C4 128.74(15) . . ?
N1 C1 C4 106.10(14) . . ?
C4 C3 C2 108.01(14) . . ?
C8 C3 C4 121.27(16) . . ?
C8 C3 C2 130.70(15) . . ?
C10 C9 C2 171.46(17) . . ?
C3 C4 C1 108.14(14) . . ?
C5 C4 C1 130.58(15) . . ?
C5 C4 C3 121.25(16) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.62(15) . . ?
C14 C13 H13 119.2 . . ?
N1 C2 C3 105.40(13) . . ?
C9 C2 N1 127.52(16) . . ?
C9 C2 C3 127.08(15) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C25 C24 C23 120.72(16) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.38(15) . . ?
C24 C23 H23 119.8 . . ?
C22 C10 C11 119.48(13) . . ?
C9 C10 C22 121.13(15) . . ?
C9 C10 C11 119.38(14) . . ?
C15 C16 C11 119.85(14) . . ?
C17 C16 C15 118.81(16) . . ?
C17 C16 C11 121.12(15) . . ?
C12 C11 C21 102.44(12) . . ?
C10 C11 C12 109.66(13) . . ?
C10 C11 C21 110.74(13) . . ?
C16 C11 C12 114.93(13) . . ?
C16 C11 C10 111.84(13) . . ?
C16 C11 C21 106.77(13) . . ?
C15 C14 H14 118.3 . . ?
C13 C14 C15 123.49(15) . . ?
C13 C14 H14 118.3 . . ?
C27 C26 H26 120.1 . . ?
C27 C26 C25 119.89(16) . . ?
C25 C26 H26 120.1 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.74(16) . . ?
C18 C17 H17 119.6 . . ?
C11 C21 H21A 109.5 . . ?
C11 C21 H21B 109.5 . . ?
C11 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 C27 H27 119.4 . . ?
C26 C27 C22 121.11(16) . . ?
C26 C27 H27 119.4 . . ?
C4 C5 H5 121.3 . . ?
C6 C5 C4 117.45(16) . . ?
C6 C5 H5 121.3 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.82(16) . . ?
C19 C20 H20 119.6 . . ?
C24 C25 C26 119.57(15) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C3 C8 H8 121.3 . . ?
C7 C8 C3 117.48(16) . . ?
C7 C8 H8 121.3 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.39(17) . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 121.15(17) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C20 C19 H19 120.3 . . ?
C20 C19 C18 119.43(17) . . ?
C18 C19 H19 120.3 . . ?
C17 C18 C19 120.55(17) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
O3 C28 C29 122.16(14) . 2_655 ?
O3 C28 C29 122.15(14) . . ?
C29 C28 C29 115.7(3) 2_655 . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
O1 C1 C4 C3 177.84(16) . . . . ?
O1 C1 C4 C5 -0.3(3) . . . . ?
O2 C12 C13 C14 -173.32(15) . . . . ?
O2 C12 C11 C10 37.33(19) . . . . ?
O2 C12 C11 C16 164.32(14) . . . . ?
O2 C12 C11 C21 -80.31(17) . . . . ?
N1 C1 C4 C3 -0.68(17) . . . . ?
N1 C1 C4 C5 -178.85(16) . . . . ?
C22 C10 C11 C12 63.61(18) . . . . ?
C22 C10 C11 C16 -65.11(18) . . . . ?
C22 C10 C11 C21 175.94(14) . . . . ?
C12 C13 C14 C15 1.4(2) . . . . ?
C15 C16 C11 C12 18.0(2) . . . . ?
C15 C16 C11 C10 143.91(14) . . . . ?
C15 C16 C11 C21 -94.81(16) . . . . ?
C15 C16 C17 C18 -0.6(2) . . . . ?
C15 C20 C19 C18 0.2(3) . . . . ?
C1 N1 C2 C3 0.58(17) . . . . ?
C1 N1 C2 C9 -178.85(16) . . . . ?
C1 C4 C5 C6 176.89(16) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C3 C8 C7 C6 -0.8(2) . . . . ?
C9 C10 C11 C12 -115.37(16) . . . . ?
C9 C10 C11 C16 115.91(17) . . . . ?
C9 C10 C11 C21 -3.0(2) . . . . ?
C4 C3 C2 N1 -1.00(17) . . . . ?
C4 C3 C2 C9 178.44(16) . . . . ?
C4 C3 C8 C7 -0.1(2) . . . . ?
C4 C5 C6 C7 0.2(2) . . . . ?
C13 C12 C11 C10 -148.59(13) . . . . ?
C13 C12 C11 C16 -21.60(19) . . . . ?
C13 C12 C11 C21 93.77(16) . . . . ?
C2 N1 C1 O1 -178.56(15) . . . . ?
C2 N1 C1 C4 0.03(17) . . . . ?
C2 C3 C4 C1 1.04(17) . . . . ?
C2 C3 C4 C5 179.41(14) . . . . ?
C2 C3 C8 C7 -178.06(16) . . . . ?
C23 C22 C10 C9 176.28(16) . . . . ?
C23 C22 C10 C11 -2.7(2) . . . . ?
C23 C22 C27 C26 -0.2(2) . . . . ?
C23 C24 C25 C26 0.2(3) . . . . ?
C10 C22 C23 C24 -176.12(15) . . . . ?
C10 C22 C27 C26 177.11(15) . . . . ?
C16 C15 C14 C13 -5.7(2) . . . . ?
C16 C15 C20 C19 -0.9(2) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C11 C12 C13 C14 12.7(2) . . . . ?
C11 C16 C17 C18 -175.19(15) . . . . ?
C14 C15 C16 C11 -4.9(2) . . . . ?
C14 C15 C16 C17 -179.62(15) . . . . ?
C14 C15 C20 C19 179.80(15) . . . . ?
C17 C16 C11 C12 -167.38(14) . . . . ?
C17 C16 C11 C10 -41.5(2) . . . . ?
C17 C16 C11 C21 79.77(18) . . . . ?
C27 C22 C23 C24 1.1(2) . . . . ?
C27 C22 C10 C9 -0.9(2) . . . . ?
C27 C22 C10 C11 -179.88(15) . . . . ?
C27 C26 C25 C24 0.7(3) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C20 C15 C16 C11 175.78(14) . . . . ?
C20 C15 C16 C17 1.1(2) . . . . ?
C20 C15 C14 C13 173.58(15) . . . . ?
C20 C19 C18 C17 0.3(3) . . . . ?
C25 C24 C23 C22 -1.2(2) . . . . ?
C25 C26 C27 C22 -0.7(3) . . . . ?
C8 C3 C4 C1 -177.37(14) . . . . ?
C8 C3 C4 C5 1.0(2) . . . . ?
C8 C3 C2 N1 177.20(16) . . . . ?
C8 C3 C2 C9 -3.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cxy1938_0m
_database_code_depnum_ccdc_archive 'CCDC 2294540'
loop_
_audit_author_name
_audit_author_address
'Pengfei Li'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2023-09-12 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_audit_creation_date             2022-06-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H19 N O2'
_chemical_formula_sum            'C27 H19 N O2'
_chemical_formula_weight         389.43
_chemical_absolute_configuration ad
_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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   7.8226(5)
_cell_length_b                   9.8700(6)
_cell_length_c                   13.4677(8)
_cell_angle_alpha                72.435(2)
_cell_angle_beta                 82.536(2)
_cell_angle_gamma                83.621(2)
_cell_volume                     980.10(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9824
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      74.72
_cell_measurement_theta_min      3.46
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0855 before and 0.0563 after correction. The Ratio of minimum to maximum transmission is 0.9146. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            38301
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.726
_diffrn_reflns_theta_min         3.460
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                7449
_reflns_number_total             7748
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2014'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 3501 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_coef       0.0114(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         7748
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.031
_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)+(0.0459P)²+0.1830P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0797
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C23(H23), C27(H27), C7(H7), C11(H11), C17(H17), C22(H22), C25(H25),
 C16(H16), C14(H14), C15(H15), C24(H24), C8(H8), C26(H26), C10(H10), C9(H9),
 C51(H51), C50(H50), C35(H35), C38(H38), C37(H37), C39(H39), C45(H45), C42(H42),
  C36(H36), C32(H32), C43(H43), C52(H52), C55(H55), C44(H44), C54(H54), C53(H53)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C56(H56A,H56B,H56C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1197(2) 0.61918(16) 0.72718(12) 0.0257(3) Uani 1 1 d . . . . .
O2 O 0.4873(2) -0.01504(17) 0.85522(13) 0.0281(4) Uani 1 1 d . . . . .
N1 N 0.2379(2) 0.38838(19) 0.79819(13) 0.0199(4) Uani 1 1 d . . . . .
C6 C 0.1971(3) 0.0485(2) 0.82029(16) 0.0201(4) Uani 1 1 d . . . . .
C12 C 0.2698(3) 0.4020(2) 0.96264(16) 0.0194(4) Uani 1 1 d . . . . .
C13 C 0.1964(3) 0.5328(2) 0.90695(16) 0.0197(4) Uani 1 1 d . . . . .
C3 C 0.2931(3) 0.3066(2) 0.89553(16) 0.0185(4) Uani 1 1 d . . . . .
C4 C 0.3534(3) 0.1687(2) 0.92312(16) 0.0213(4) Uani 1 1 d . . . . .
H4 H 0.398510 0.133571 0.989102 0.026 Uiso 1 1 calc R U . . .
C1 C 0.1751(3) 0.5270(2) 0.80067(16) 0.0208(4) Uani 1 1 d . . . . .
C23 C 0.4829(3) 0.3357(2) 0.68062(17) 0.0246(4) Uani 1 1 d . . . . .
H23 H 0.556805 0.344473 0.728674 0.030 Uiso 1 1 calc R U . . .
C27 C 0.1554(3) 0.3068(2) 0.46298(16) 0.0230(4) Uani 1 1 d . . . . .
H27 H 0.033590 0.324954 0.473849 0.028 Uiso 1 1 calc R U . . .
C7 C 0.0350(3) 0.0740(2) 0.87127(17) 0.0235(4) Uani 1 1 d . . . . .
H7 H 0.026101 0.112522 0.928577 0.028 Uiso 1 1 calc R U . . .
C11 C 0.2095(3) -0.0034(2) 0.73385(18) 0.0256(5) Uani 1 1 d . . . . .
H11 H 0.319552 -0.021150 0.699024 0.031 Uiso 1 1 calc R U . . .
C17 C 0.3061(3) 0.3767(2) 1.06522(17) 0.0225(4) Uani 1 1 d . . . . .
H17 H 0.352694 0.286081 1.104311 0.027 Uiso 1 1 calc R U . . .
C22 C 0.5516(3) 0.3022(2) 0.59182(17) 0.0268(5) Uani 1 1 d . . . . .
H22 H 0.673247 0.285747 0.578894 0.032 Uiso 1 1 calc R U . . .
C28 C -0.0027(3) 0.3697(2) 0.65677(17) 0.0230(4) Uani 1 1 d . . . . .
H28A H -0.029186 0.382692 0.726609 0.034 Uiso 1 1 calc R U . . .
H28B H -0.055314 0.285031 0.654885 0.034 Uiso 1 1 calc R U . . .
H28C H -0.049077 0.453693 0.604637 0.034 Uiso 1 1 calc R U . . .
C19 C 0.1886(3) 0.3508(2) 0.63271(16) 0.0207(4) Uani 1 1 d . . . . .
C18 C 0.3004(3) 0.3574(2) 0.70115(16) 0.0208(4) Uani 1 1 d . . . . .
C25 C 0.4063(3) 0.2438(2) 0.35681(18) 0.0266(5) Uani 1 1 d . . . . .
H25 H 0.453906 0.218170 0.295814 0.032 Uiso 1 1 calc R U . . .
C16 C 0.2714(3) 0.4895(3) 1.10812(17) 0.0255(5) Uani 1 1 d . . . . .
H16 H 0.296820 0.476306 1.177643 0.031 Uiso 1 1 calc R U . . .
C14 C 0.1588(3) 0.6450(2) 0.95020(18) 0.0235(4) Uani 1 1 d . . . . .
H14 H 0.107122 0.733977 0.912006 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3577(3) 0.0654(2) 0.86277(16) 0.0202(4) Uani 1 1 d . . . . .
C15 C 0.1998(3) 0.6220(2) 1.05132(19) 0.0269(5) Uani 1 1 d . . . . .
H15 H 0.178817 0.697425 1.082546 0.032 Uiso 1 1 calc R U . . .
C21 C 0.4426(3) 0.2918(2) 0.51885(17) 0.0234(4) Uani 1 1 d . . . . .
C24 C 0.5132(3) 0.2547(2) 0.42655(17) 0.0271(5) Uani 1 1 d . . . . .
H24 H 0.634722 0.237469 0.413406 0.033 Uiso 1 1 calc R U . . .
C20 C 0.2606(3) 0.3178(2) 0.53778(17) 0.0206(4) Uani 1 1 d . . . . .
C8 C -0.1129(3) 0.0431(3) 0.8383(2) 0.0298(5) Uani 1 1 d . . . . .
H8 H -0.222884 0.056775 0.874603 0.036 Uiso 1 1 calc R U . . .
C26 C 0.2264(3) 0.2705(2) 0.37523(17) 0.0257(5) Uani 1 1 d . . . . .
H26 H 0.153300 0.263254 0.326254 0.031 Uiso 1 1 calc R U . . .
C10 C 0.0605(3) -0.0290(3) 0.6990(2) 0.0316(5) Uani 1 1 d . . . . .
H10 H 0.068010 -0.061052 0.638678 0.038 Uiso 1 1 calc R U . . .
C9 C -0.0995(3) -0.0079(3) 0.7521(2) 0.0329(6) Uani 1 1 d . . . . .
H9 H -0.200812 -0.028556 0.729240 0.039 Uiso 1 1 calc R U . . .
O4 O 0.50896(19) 1.00381(17) 0.16252(13) 0.0261(3) Uani 1 1 d . . . . .
O3 O 0.8685(2) 0.36380(16) 0.26998(12) 0.0242(3) Uani 1 1 d . . . . .
N2 N 0.7655(2) 0.59940(18) 0.20495(13) 0.0182(4) Uani 1 1 d . . . . .
C49 C 0.7681(3) 0.7028(2) 0.48698(16) 0.0201(4) Uani 1 1 d . . . . .
C51 C 0.9200(3) 0.6363(2) 0.33894(16) 0.0195(4) Uani 1 1 d . . . . .
H51 H 1.025014 0.614814 0.300659 0.023 Uiso 1 1 calc R U . . .
C31 C 0.7037(3) 0.6890(2) 0.11179(16) 0.0184(4) Uani 1 1 d . . . . .
C33 C 0.6419(3) 0.9288(2) 0.15148(16) 0.0196(4) Uani 1 1 d . . . . .
C29 C 0.8143(3) 0.4605(2) 0.19893(16) 0.0194(4) Uani 1 1 d . . . . .
C46 C 0.7602(3) 0.6326(2) 0.30211(15) 0.0180(4) Uani 1 1 d . . . . .
C48 C 0.6076(3) 0.6937(2) 0.45150(16) 0.0197(4) Uani 1 1 d . . . . .
C41 C 0.7804(3) 0.4621(2) 0.09335(16) 0.0197(4) Uani 1 1 d . . . . .
C50 C 0.9240(3) 0.6705(2) 0.42919(16) 0.0206(4) Uani 1 1 d . . . . .
H50 H 1.031950 0.672843 0.453615 0.025 Uiso 1 1 calc R U . . .
C47 C 0.6040(3) 0.6559(2) 0.35719(15) 0.0177(4) Uani 1 1 d . . . . .
C35 C 0.9634(3) 0.9218(2) 0.13960(17) 0.0203(4) Uani 1 1 d . . . . .
H35 H 0.970191 0.883744 0.082186 0.024 Uiso 1 1 calc R U . . .
C40 C 0.7118(3) 0.5978(2) 0.04185(16) 0.0191(4) Uani 1 1 d . . . . .
C38 C 0.9439(3) 1.0278(2) 0.31020(17) 0.0238(4) Uani 1 1 d . . . . .
H38 H 0.937820 1.062017 0.369454 0.029 Uiso 1 1 calc R U . . .
C37 C 1.1037(3) 1.0031(2) 0.25762(19) 0.0251(5) Uani 1 1 d . . . . .
H37 H 1.206174 1.022219 0.280195 0.030 Uiso 1 1 calc R U . . .
C39 C 0.7934(3) 1.0028(2) 0.27670(17) 0.0215(4) Uani 1 1 d . . . . .
H39 H 0.684287 1.022181 0.311776 0.026 Uiso 1 1 calc R U . . .
C56 C 0.4335(3) 0.6420(2) 0.32175(17) 0.0221(4) Uani 1 1 d . . . . .
H56A H 0.370413 0.736043 0.300910 0.033 Uiso 1 1 calc R U . . .
H56B H 0.364915 0.577905 0.379296 0.033 Uiso 1 1 calc R U . . .
H56C H 0.454283 0.603114 0.261988 0.033 Uiso 1 1 calc R U . . .
C34 C 0.8026(3) 0.9489(2) 0.19122(16) 0.0188(4) Uani 1 1 d . . . . .
C45 C 0.6684(3) 0.6295(2) -0.06029(16) 0.0224(4) Uani 1 1 d . . . . .
H45 H 0.622364 0.721975 -0.096211 0.027 Uiso 1 1 calc R U . . .
C42 C 0.8074(3) 0.3529(2) 0.04654(17) 0.0232(4) Uani 1 1 d . . . . .
H42 H 0.854066 0.260694 0.082527 0.028 Uiso 1 1 calc R U . . .
C36 C 1.1139(3) 0.9505(2) 0.17193(17) 0.0228(4) Uani 1 1 d . . . . .
H36 H 1.223086 0.934255 0.135662 0.027 Uiso 1 1 calc R U . . .
C32 C 0.6456(3) 0.8269(2) 0.08888(16) 0.0196(4) Uani 1 1 d . . . . .
H32 H 0.600277 0.865190 0.023137 0.024 Uiso 1 1 calc R U . . .
C43 C 0.7634(3) 0.3839(2) -0.05498(18) 0.0256(5) Uani 1 1 d . . . . .
H43 H 0.779755 0.311604 -0.089270 0.031 Uiso 1 1 calc R U . . .
C52 C 0.7703(3) 0.7421(2) 0.57983(17) 0.0255(5) Uani 1 1 d . . . . .
H52 H 0.877556 0.747832 0.603739 0.031 Uiso 1 1 calc R U . . .
C55 C 0.4529(3) 0.7227(2) 0.51227(17) 0.0256(5) Uani 1 1 d . . . . .
H55 H 0.344046 0.715686 0.490851 0.031 Uiso 1 1 calc R U . . .
C44 C 0.6951(3) 0.5205(2) -0.10761(18) 0.0256(5) Uani 1 1 d . . . . .
H44 H 0.666342 0.538999 -0.177120 0.031 Uiso 1 1 calc R U . . .
C54 C 0.4595(3) 0.7608(3) 0.60156(19) 0.0310(5) Uani 1 1 d . . . . .
H54 H 0.354976 0.779938 0.641195 0.037 Uiso 1 1 calc R U . . .
C53 C 0.6184(3) 0.7719(3) 0.63515(18) 0.0296(5) Uani 1 1 d . . . . .
H53 H 0.620653 0.800123 0.696416 0.036 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 C1 1.215(3) . ?
O2 C5 1.229(3) . ?
N1 C3 1.410(3) . ?
N1 C1 1.410(3) . ?
N1 C18 1.443(3) . ?
C6 C7 1.396(3) . ?
C6 C11 1.395(3) . ?
C6 C5 1.492(3) . ?
C12 C13 1.386(3) . ?
C12 C3 1.474(3) . ?
C12 C17 1.389(3) . ?
C13 C1 1.481(3) . ?
C13 C14 1.387(3) . ?
C3 C4 1.345(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.479(3) . ?
C23 H23 0.9500 . ?
C23 C22 1.364(3) . ?
C23 C18 1.424(3) . ?
C27 H27 0.9500 . ?
C27 C20 1.416(3) . ?
C27 C26 1.369(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.386(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.388(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.414(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C28 C19 1.492(3) . ?
C19 C18 1.370(3) . ?
C19 C20 1.443(3) . ?
C25 H25 0.9500 . ?
C25 C24 1.370(3) . ?
C25 C26 1.407(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.398(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9500 . ?
C21 C24 1.427(3) . ?
C21 C20 1.422(3) . ?
C24 H24 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.386(4) . ?
C26 H26 0.9500 . ?
C10 H10 0.9500 . ?
C10 C9 1.385(4) . ?
C9 H9 0.9500 . ?
O4 C33 1.227(3) . ?
O3 C29 1.213(3) . ?
N2 C31 1.408(3) . ?
N2 C29 1.406(3) . ?
N2 C46 1.436(2) . ?
C49 C48 1.421(3) . ?
C49 C50 1.418(3) . ?
C49 C52 1.419(3) . ?
C51 H51 0.9500 . ?
C51 C46 1.412(3) . ?
C51 C50 1.361(3) . ?
C31 C40 1.478(3) . ?
C31 C32 1.341(3) . ?
C33 C34 1.483(3) . ?
C33 C32 1.491(3) . ?
C29 C41 1.475(3) . ?
C46 C47 1.379(3) . ?
C48 C47 1.432(3) . ?
C48 C55 1.422(3) . ?
C41 C40 1.393(3) . ?
C41 C42 1.388(3) . ?
C50 H50 0.9500 . ?
C47 C56 1.507(3) . ?
C35 H35 0.9500 . ?
C35 C34 1.396(3) . ?
C35 C36 1.392(3) . ?
C40 C45 1.394(3) . ?
C38 H38 0.9500 . ?
C38 C37 1.389(3) . ?
C38 C39 1.386(3) . ?
C37 H37 0.9500 . ?
C37 C36 1.391(3) . ?
C39 H39 0.9500 . ?
C39 C34 1.397(3) . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
C45 H45 0.9500 . ?
C45 C44 1.392(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.389(3) . ?
C36 H36 0.9500 . ?
C32 H32 0.9500 . ?
C43 H43 0.9500 . ?
C43 C44 1.402(3) . ?
C52 H52 0.9500 . ?
C52 C53 1.371(3) . ?
C55 H55 0.9500 . ?
C55 C54 1.372(3) . ?
C44 H44 0.9500 . ?
C54 H54 0.9500 . ?
C54 C53 1.402(4) . ?
C53 H53 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C1 111.00(17) . . ?
C3 N1 C18 122.94(17) . . ?
C1 N1 C18 121.67(17) . . ?
C7 C6 C5 120.29(19) . . ?
C11 C6 C7 119.9(2) . . ?
C11 C6 C5 119.65(19) . . ?
C13 C12 C3 108.42(18) . . ?
C13 C12 C17 121.37(19) . . ?
C17 C12 C3 130.2(2) . . ?
C12 C13 C1 108.58(17) . . ?
C12 C13 C14 121.67(19) . . ?
C14 C13 C1 129.7(2) . . ?
N1 C3 C12 106.17(17) . . ?
C4 C3 N1 127.49(19) . . ?
C4 C3 C12 126.3(2) . . ?
C3 C4 H4 116.2 . . ?
C3 C4 C5 127.6(2) . . ?
C5 C4 H4 116.2 . . ?
O1 C1 N1 124.55(19) . . ?
O1 C1 C13 129.7(2) . . ?
N1 C1 C13 105.76(17) . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C18 119.9(2) . . ?
C18 C23 H23 120.1 . . ?
C20 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C26 C27 C20 121.0(2) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.0(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C11 H11 120.2 . . ?
C10 C11 C6 119.7(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C17 H17 121.5 . . ?
C16 C17 C12 117.1(2) . . ?
C16 C17 H17 121.5 . . ?
C23 C22 H22 119.8 . . ?
C23 C22 C21 120.4(2) . . ?
C21 C22 H22 119.8 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C19 C28 H28A 109.5 . . ?
C19 C28 H28B 109.5 . . ?
C19 C28 H28C 109.5 . . ?
C18 C19 C28 121.71(19) . . ?
C18 C19 C20 118.02(18) . . ?
C20 C19 C28 120.20(18) . . ?
C23 C18 N1 116.42(18) . . ?
C19 C18 N1 121.21(19) . . ?
C19 C18 C23 122.37(19) . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.2(2) . . ?
C26 C25 H25 119.9 . . ?
C17 C16 H16 119.3 . . ?
C17 C16 C15 121.5(2) . . ?
C15 C16 H16 119.3 . . ?
C13 C14 H14 121.3 . . ?
C15 C14 C13 117.3(2) . . ?
C15 C14 H14 121.3 . . ?
O2 C5 C6 119.65(19) . . ?
O2 C5 C4 120.65(19) . . ?
C4 C5 C6 119.38(18) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C22 C21 C24 120.7(2) . . ?
C22 C21 C20 119.76(19) . . ?
C20 C21 C24 119.51(19) . . ?
C25 C24 C21 120.2(2) . . ?
C25 C24 H24 119.9 . . ?
C21 C24 H24 119.9 . . ?
C27 C20 C19 122.15(19) . . ?
C27 C20 C21 118.27(19) . . ?
C21 C20 C19 119.57(18) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8 120.2 . . ?
C27 C26 C25 120.7(2) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 C11 120.1(2) . . ?
C9 C10 H10 120.0 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C31 N2 C46 126.55(17) . . ?
C29 N2 C31 112.06(16) . . ?
C29 N2 C46 120.85(17) . . ?
C50 C49 C48 119.10(18) . . ?
C50 C49 C52 121.08(19) . . ?
C52 C49 C48 119.81(19) . . ?
C46 C51 H51 119.9 . . ?
C50 C51 H51 119.9 . . ?
C50 C51 C46 120.14(19) . . ?
N2 C31 C40 105.27(17) . . ?
C32 C31 N2 128.97(19) . . ?
C32 C31 C40 125.74(19) . . ?
O4 C33 C34 120.35(19) . . ?
O4 C33 C32 119.50(19) . . ?
C34 C33 C32 119.90(18) . . ?
O3 C29 N2 124.19(19) . . ?
O3 C29 C41 130.3(2) . . ?
N2 C29 C41 105.50(17) . . ?
C51 C46 N2 117.23(17) . . ?
C47 C46 N2 120.45(18) . . ?
C47 C46 C51 122.30(18) . . ?
C49 C48 C47 120.27(17) . . ?
C49 C48 C55 118.12(19) . . ?
C55 C48 C47 121.61(19) . . ?
C40 C41 C29 108.57(17) . . ?
C42 C41 C29 129.3(2) . . ?
C42 C41 C40 122.1(2) . . ?
C49 C50 H50 119.8 . . ?
C51 C50 C49 120.43(19) . . ?
C51 C50 H50 119.8 . . ?
C46 C47 C48 117.63(18) . . ?
C46 C47 C56 122.36(18) . . ?
C48 C47 C56 120.01(17) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C36 C35 C34 120.2(2) . . ?
C41 C40 C31 108.56(18) . . ?
C41 C40 C45 120.72(19) . . ?
C45 C40 C31 130.7(2) . . ?
C37 C38 H38 119.8 . . ?
C39 C38 H38 119.8 . . ?
C39 C38 C37 120.4(2) . . ?
C38 C37 H37 119.9 . . ?
C38 C37 C36 120.1(2) . . ?
C36 C37 H37 119.9 . . ?
C38 C39 H39 120.1 . . ?
C38 C39 C34 119.9(2) . . ?
C34 C39 H39 120.1 . . ?
C47 C56 H56A 109.5 . . ?
C47 C56 H56B 109.5 . . ?
C47 C56 H56C 109.5 . . ?
H56A C56 H56B 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C35 C34 C33 120.04(19) . . ?
C35 C34 C39 119.67(19) . . ?
C39 C34 C33 120.19(18) . . ?
C40 C45 H45 121.3 . . ?
C44 C45 C40 117.4(2) . . ?
C44 C45 H45 121.3 . . ?
C41 C42 H42 121.3 . . ?
C41 C42 C43 117.3(2) . . ?
C43 C42 H42 121.3 . . ?
C35 C36 H36 120.2 . . ?
C37 C36 C35 119.7(2) . . ?
C37 C36 H36 120.2 . . ?
C31 C32 C33 129.47(19) . . ?
C31 C32 H32 115.3 . . ?
C33 C32 H32 115.3 . . ?
C42 C43 H43 119.5 . . ?
C42 C43 C44 120.9(2) . . ?
C44 C43 H43 119.5 . . ?
C49 C52 H52 119.8 . . ?
C53 C52 C49 120.3(2) . . ?
C53 C52 H52 119.8 . . ?
C48 C55 H55 119.7 . . ?
C54 C55 C48 120.6(2) . . ?
C54 C55 H55 119.7 . . ?
C45 C44 C43 121.5(2) . . ?
C45 C44 H44 119.3 . . ?
C43 C44 H44 119.3 . . ?
C55 C54 H54 119.5 . . ?
C55 C54 C53 121.0(2) . . ?
C53 C54 H54 119.5 . . ?
C52 C53 C54 120.2(2) . . ?
C52 C53 H53 119.9 . . ?
C54 C53 H53 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C3 C4 C5 -7.7(4) . . . . ?
C6 C7 C8 C9 -2.5(3) . . . . ?
C6 C11 C10 C9 -2.3(3) . . . . ?
C12 C13 C1 O1 -178.2(2) . . . . ?
C12 C13 C1 N1 0.4(2) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C12 C3 C4 C5 171.59(19) . . . . ?
C12 C17 C16 C15 1.2(3) . . . . ?
C13 C12 C3 N1 2.5(2) . . . . ?
C13 C12 C3 C4 -176.8(2) . . . . ?
C13 C12 C17 C16 -2.2(3) . . . . ?
C13 C14 C15 C16 -1.8(3) . . . . ?
C3 N1 C1 O1 179.9(2) . . . . ?
C3 N1 C1 C13 1.3(2) . . . . ?
C3 N1 C18 C23 -49.2(3) . . . . ?
C3 N1 C18 C19 131.3(2) . . . . ?
C3 C12 C13 C1 -1.8(2) . . . . ?
C3 C12 C13 C14 179.94(19) . . . . ?
C3 C12 C17 C16 179.4(2) . . . . ?
C3 C4 C5 O2 135.7(2) . . . . ?
C3 C4 C5 C6 -50.7(3) . . . . ?
C1 N1 C3 C12 -2.3(2) . . . . ?
C1 N1 C3 C4 177.0(2) . . . . ?
C1 N1 C18 C23 105.1(2) . . . . ?
C1 N1 C18 C19 -74.3(3) . . . . ?
C1 C13 C14 C15 -177.1(2) . . . . ?
C23 C22 C21 C24 -179.0(2) . . . . ?
C23 C22 C21 C20 0.6(3) . . . . ?
C7 C6 C11 C10 0.1(3) . . . . ?
C7 C6 C5 O2 144.7(2) . . . . ?
C7 C6 C5 C4 -28.9(3) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C11 C6 C7 C8 2.3(3) . . . . ?
C11 C6 C5 O2 -30.4(3) . . . . ?
C11 C6 C5 C4 155.9(2) . . . . ?
C11 C10 C9 C8 2.0(4) . . . . ?
C17 C12 C13 C1 179.54(19) . . . . ?
C17 C12 C13 C14 1.3(3) . . . . ?
C17 C12 C3 N1 -178.9(2) . . . . ?
C17 C12 C3 C4 1.7(4) . . . . ?
C17 C16 C15 C14 0.8(4) . . . . ?
C22 C23 C18 N1 178.3(2) . . . . ?
C22 C23 C18 C19 -2.3(3) . . . . ?
C22 C21 C24 C25 179.5(2) . . . . ?
C22 C21 C20 C27 179.9(2) . . . . ?
C22 C21 C20 C19 -1.6(3) . . . . ?
C28 C19 C18 N1 -2.4(3) . . . . ?
C28 C19 C18 C23 178.2(2) . . . . ?
C28 C19 C20 C27 2.2(3) . . . . ?
C28 C19 C20 C21 -176.28(18) . . . . ?
C18 N1 C3 C12 154.42(18) . . . . ?
C18 N1 C3 C4 -26.2(3) . . . . ?
C18 N1 C1 O1 22.8(3) . . . . ?
C18 N1 C1 C13 -155.81(18) . . . . ?
C18 C23 C22 C21 1.3(3) . . . . ?
C18 C19 C20 C27 179.14(19) . . . . ?
C18 C19 C20 C21 0.7(3) . . . . ?
C14 C13 C1 O1 -0.1(4) . . . . ?
C14 C13 C1 N1 178.5(2) . . . . ?
C5 C6 C7 C8 -172.9(2) . . . . ?
C5 C6 C11 C10 175.32(19) . . . . ?
C24 C25 C26 C27 -0.4(3) . . . . ?
C24 C21 C20 C27 -0.5(3) . . . . ?
C24 C21 C20 C19 178.0(2) . . . . ?
C20 C27 C26 C25 -0.3(3) . . . . ?
C20 C19 C18 N1 -179.37(18) . . . . ?
C20 C19 C18 C23 1.3(3) . . . . ?
C20 C21 C24 C25 -0.2(3) . . . . ?
C26 C27 C20 C19 -177.70(19) . . . . ?
C26 C27 C20 C21 0.8(3) . . . . ?
C26 C25 C24 C21 0.6(3) . . . . ?
O4 C33 C34 C35 -148.5(2) . . . . ?
O4 C33 C34 C39 27.8(3) . . . . ?
O4 C33 C32 C31 -132.6(2) . . . . ?
O3 C29 C41 C40 177.5(2) . . . . ?
O3 C29 C41 C42 -2.2(4) . . . . ?
N2 C31 C40 C41 -1.5(2) . . . . ?
N2 C31 C40 C45 -179.4(2) . . . . ?
N2 C31 C32 C33 5.3(4) . . . . ?
N2 C29 C41 C40 -0.9(2) . . . . ?
N2 C29 C41 C42 179.3(2) . . . . ?
N2 C46 C47 C48 -177.74(17) . . . . ?
N2 C46 C47 C56 2.6(3) . . . . ?
C49 C48 C47 C46 -1.5(3) . . . . ?
C49 C48 C47 C56 178.12(18) . . . . ?
C49 C48 C55 C54 1.1(3) . . . . ?
C49 C52 C53 C54 1.3(3) . . . . ?
C51 C46 C47 C48 4.0(3) . . . . ?
C51 C46 C47 C56 -175.68(18) . . . . ?
C31 N2 C29 O3 -178.7(2) . . . . ?
C31 N2 C29 C41 -0.1(2) . . . . ?
C31 N2 C46 C51 -117.2(2) . . . . ?
C31 N2 C46 C47 64.4(3) . . . . ?
C31 C40 C45 C44 178.2(2) . . . . ?
C29 N2 C31 C40 1.0(2) . . . . ?
C29 N2 C31 C32 179.8(2) . . . . ?
C29 N2 C46 C51 72.0(2) . . . . ?
C29 N2 C46 C47 -106.4(2) . . . . ?
C29 C41 C40 C31 1.5(2) . . . . ?
C29 C41 C40 C45 179.66(19) . . . . ?
C29 C41 C42 C43 179.9(2) . . . . ?
C46 N2 C31 C40 -170.57(18) . . . . ?
C46 N2 C31 C32 8.2(3) . . . . ?
C46 N2 C29 O3 -6.6(3) . . . . ?
C46 N2 C29 C41 172.02(17) . . . . ?
C46 C51 C50 C49 0.0(3) . . . . ?
C48 C49 C50 C51 2.3(3) . . . . ?
C48 C49 C52 C53 -0.3(3) . . . . ?
C48 C55 C54 C53 -0.1(3) . . . . ?
C41 C40 C45 C44 0.5(3) . . . . ?
C41 C42 C43 C44 0.2(3) . . . . ?
C50 C49 C48 C47 -1.5(3) . . . . ?
C50 C49 C48 C55 178.30(19) . . . . ?
C50 C49 C52 C53 -179.5(2) . . . . ?
C50 C51 C46 N2 178.36(18) . . . . ?
C50 C51 C46 C47 -3.3(3) . . . . ?
C47 C48 C55 C54 -179.0(2) . . . . ?
C40 C31 C32 C33 -176.1(2) . . . . ?
C40 C41 C42 C43 0.2(3) . . . . ?
C40 C45 C44 C43 -0.2(3) . . . . ?
C38 C37 C36 C35 -0.4(3) . . . . ?
C38 C39 C34 C33 -176.8(2) . . . . ?
C38 C39 C34 C35 -0.6(3) . . . . ?
C37 C38 C39 C34 1.7(3) . . . . ?
C39 C38 C37 C36 -1.2(3) . . . . ?
C34 C33 C32 C31 53.2(3) . . . . ?
C34 C35 C36 C37 1.5(3) . . . . ?
C42 C41 C40 C31 -178.67(19) . . . . ?
C42 C41 C40 C45 -0.5(3) . . . . ?
C42 C43 C44 C45 -0.2(4) . . . . ?
C36 C35 C34 C33 175.25(19) . . . . ?
C36 C35 C34 C39 -1.0(3) . . . . ?
C32 C31 C40 C41 179.6(2) . . . . ?
C32 C31 C40 C45 1.7(4) . . . . ?
C32 C33 C34 C35 25.7(3) . . . . ?
C32 C33 C34 C39 -158.08(19) . . . . ?
C52 C49 C48 C47 179.20(18) . . . . ?
C52 C49 C48 C55 -1.0(3) . . . . ?
C52 C49 C50 C51 -178.43(19) . . . . ?
C55 C48 C47 C46 178.6(2) . . . . ?
C55 C48 C47 C56 -1.7(3) . . . . ?
C55 C54 C53 C52 -1.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
