# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

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

data_3a
_database_code_depnum_ccdc_archive 'CCDC 2077430'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan'
;Yangzhou University
China
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C50 H39 F N2 O3'
_chemical_formula_sum            'C50 H39 F N2 O3'
_chemical_formula_weight         734.83

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.874(3)
_cell_length_b                   13.417(3)
_cell_length_c                   14.271(3)
_cell_angle_alpha                62.751(6)
_cell_angle_beta                 75.230(7)
_cell_angle_gamma                82.876(6)
_cell_volume                     1954.4(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5116
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      23.42

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             772
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22269
_diffrn_reflns_av_unetI/netI     0.1114
_diffrn_reflns_av_R_equivalents  0.1010
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.216
_diffrn_reflns_theta_max         24.712
_diffrn_reflns_theta_full        24.712
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             6468
_reflns_number_gt                3363
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0920P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6468
_refine_ls_number_parameters     509
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1620
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1796
_refine_ls_wR_factor_gt          0.1273
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1079(3) 0.3589(3) 0.0242(3) 0.0688(11) Uani 1 1 d . . . . .
H1 H 0.0684 0.3096 0.0927 0.083 Uiso 1 1 calc R U . . .
C2 C 0.1282(4) 0.3297(4) -0.0595(5) 0.0904(14) Uani 1 1 d . . . . .
H2 H 0.1018 0.2613 -0.0469 0.108 Uiso 1 1 calc R U . . .
C3 C 0.1864(4) 0.3999(6) -0.1605(5) 0.1009(17) Uani 1 1 d . . . . .
H3 H 0.1990 0.3804 -0.2171 0.121 Uiso 1 1 calc R U . . .
C4 C 0.2262(4) 0.4995(5) -0.1776(4) 0.1007(15) Uani 1 1 d . . . . .
H4 H 0.2680 0.5472 -0.2458 0.121 Uiso 1 1 calc R U . . .
C5 C 0.2050(3) 0.5298(4) -0.0944(3) 0.0732(11) Uani 1 1 d . . . . .
H5 H 0.2314 0.5985 -0.1076 0.088 Uiso 1 1 calc R U . . .
C6 C 0.1455(3) 0.4603(3) 0.0076(3) 0.0509(9) Uani 1 1 d . . . . .
C7 C 0.1202(3) 0.4958(3) 0.0970(3) 0.0512(8) Uani 1 1 d . . . . .
H7A H 0.1417 0.5737 0.0666 0.061 Uiso 1 1 calc R U . . .
H7B H 0.0372 0.4901 0.1285 0.061 Uiso 1 1 calc R U . . .
C8 C 0.2935(3) 0.4527(2) 0.1763(2) 0.0388(7) Uani 1 1 d . . . . .
C9 C 0.3323(2) 0.3627(2) 0.2781(2) 0.0340(7) Uani 1 1 d . . . . .
C10 C 0.2294(2) 0.2840(2) 0.3338(2) 0.0363(7) Uani 1 1 d . . . . .
C11 C 0.2108(3) 0.1872(2) 0.4298(2) 0.0458(8) Uani 1 1 d . . . . .
H11 H 0.2688 0.1551 0.4684 0.055 Uiso 1 1 calc R U . . .
C12 C 0.1018(3) 0.1406(3) 0.4657(3) 0.0578(9) Uani 1 1 d . . . . .
C13 C 0.0145(3) 0.1847(3) 0.4110(3) 0.0649(10) Uani 1 1 d . . . . .
H13 H -0.0577 0.1502 0.4392 0.078 Uiso 1 1 calc R U . . .
C14 C 0.0338(3) 0.2807(3) 0.3141(3) 0.0564(9) Uani 1 1 d . . . . .
H14 H -0.0242 0.3117 0.2753 0.068 Uiso 1 1 calc R U . . .
C15 C 0.1424(2) 0.3288(3) 0.2767(2) 0.0417(8) Uani 1 1 d . . . . .
C16 C 0.3502(2) 0.4247(2) 0.3449(2) 0.0350(7) Uani 1 1 d . . . . .
H16 H 0.3977 0.4913 0.2951 0.042 Uiso 1 1 calc R U . . .
C17 C 0.2304(2) 0.4638(2) 0.3883(2) 0.0404(7) Uani 1 1 d . . . . .
C18 C 0.1818(3) 0.5759(2) 0.3232(2) 0.0418(7) Uani 1 1 d . . . . .
C19 C 0.2500(3) 0.6654(3) 0.2448(3) 0.0525(8) Uani 1 1 d . . . . .
H19 H 0.3305 0.6566 0.2293 0.063 Uiso 1 1 calc R U . . .
C20 C 0.2005(3) 0.7684(3) 0.1886(3) 0.0596(9) Uani 1 1 d . . . . .
H20 H 0.2480 0.8278 0.1362 0.072 Uiso 1 1 calc R U . . .
C21 C 0.0816(3) 0.7833(3) 0.2099(3) 0.0607(9) Uani 1 1 d . . . . .
C22 C 0.0247(4) 0.8948(3) 0.1492(4) 0.0947(14) Uani 1 1 d . . . . .
H22A H 0.0838 0.9479 0.0977 0.142 Uiso 1 1 calc R U . . .
H22B H -0.0189 0.9220 0.1995 0.142 Uiso 1 1 calc R U . . .
H22C H -0.0266 0.8849 0.1119 0.142 Uiso 1 1 calc R U . . .
C23 C 0.0131(3) 0.6928(3) 0.2884(3) 0.0753(11) Uani 1 1 d . . . . .
H23 H -0.0674 0.7011 0.3032 0.090 Uiso 1 1 calc R U . . .
C24 C 0.0626(3) 0.5906(3) 0.3449(3) 0.0636(10) Uani 1 1 d . . . . .
H24 H 0.0152 0.5313 0.3980 0.076 Uiso 1 1 calc R U . . .
C25 C 0.4337(3) 0.3080(3) 0.0777(3) 0.0537(9) Uani 1 1 d . . . . .
H25A H 0.3507 0.3037 0.1041 0.080 Uiso 1 1 calc R U . . .
H25B H 0.4596 0.2530 0.0512 0.080 Uiso 1 1 calc R U . . .
H25C H 0.4543 0.3814 0.0202 0.080 Uiso 1 1 calc R U . . .
C26 C 0.5967(2) 0.2333(2) 0.1758(2) 0.0402(7) Uani 1 1 d . . . . .
C27 C 0.6765(3) 0.2060(3) 0.1011(3) 0.0519(8) Uani 1 1 d . . . . .
H27 H 0.6606 0.2191 0.0359 0.062 Uiso 1 1 calc R U . . .
C28 C 0.7807(3) 0.1585(3) 0.1279(3) 0.0613(10) Uani 1 1 d . . . . .
H28 H 0.8366 0.1397 0.0795 0.074 Uiso 1 1 calc R U . . .
C29 C 0.8036(3) 0.1379(3) 0.2267(3) 0.0621(10) Uani 1 1 d . . . . .
H29 H 0.8739 0.1044 0.2432 0.074 Uiso 1 1 calc R U . . .
C30 C 0.7245(3) 0.1663(3) 0.2999(3) 0.0498(8) Uani 1 1 d . . . . .
H30 H 0.7410 0.1522 0.3652 0.060 Uiso 1 1 calc R U . . .
C31 C 0.6186(2) 0.2169(2) 0.2745(2) 0.0382(7) Uani 1 1 d . . . . .
C32 C 0.5207(2) 0.2654(2) 0.3232(2) 0.0359(7) Uani 1 1 d . . . . .
C33 C 0.4461(2) 0.3072(2) 0.2541(2) 0.0359(7) Uani 1 1 d . . . . .
C34 C 0.5514(3) 0.0928(2) 0.5585(2) 0.0470(8) Uani 1 1 d . . . . .
H34 H 0.4937 0.0604 0.5481 0.056 Uiso 1 1 calc R U . . .
C35 C 0.6196(3) 0.0260(3) 0.6291(3) 0.0561(9) Uani 1 1 d . . . . .
H35 H 0.6061 -0.0507 0.6669 0.067 Uiso 1 1 calc R U . . .
C36 C 0.7077(3) 0.0700(3) 0.6454(3) 0.0534(9) Uani 1 1 d . . . . .
C37 C 0.7852(4) -0.0039(3) 0.7218(3) 0.0868(13) Uani 1 1 d . . . . .
H37A H 0.8533 0.0370 0.7077 0.130 Uiso 1 1 calc R U . . .
H37B H 0.8081 -0.0696 0.7107 0.130 Uiso 1 1 calc R U . . .
H37C H 0.7431 -0.0258 0.7952 0.130 Uiso 1 1 calc R U . . .
C38 C 0.7239(3) 0.1848(3) 0.5899(3) 0.0518(9) Uani 1 1 d . . . . .
H38 H 0.7825 0.2165 0.5999 0.062 Uiso 1 1 calc R U . . .
C39 C 0.6544(3) 0.2536(2) 0.5195(2) 0.0428(8) Uani 1 1 d . . . . .
H39 H 0.6662 0.3306 0.4837 0.051 Uiso 1 1 calc R U . . .
C40 C 0.5674(2) 0.2080(2) 0.5024(2) 0.0353(7) Uani 1 1 d . . . . .
C41 C 0.4951(2) 0.2773(2) 0.4230(2) 0.0353(7) Uani 1 1 d . . . . .
C42 C 0.4121(2) 0.3522(2) 0.4352(2) 0.0336(7) Uani 1 1 d . . . . .
C43 C 0.3907(2) 0.3845(2) 0.5246(2) 0.0375(7) Uani 1 1 d . . . . .
C44 C 0.3886(2) 0.2999(2) 0.6378(2) 0.0369(7) Uani 1 1 d . . . . .
C45 C 0.3311(3) 0.2010(3) 0.6831(3) 0.0562(9) Uani 1 1 d . . . . .
H45 H 0.2980 0.1829 0.6405 0.067 Uiso 1 1 calc R U . . .
C46 C 0.3209(3) 0.1269(3) 0.7917(3) 0.0712(11) Uani 1 1 d . . . . .
H46 H 0.2804 0.0603 0.8213 0.085 Uiso 1 1 calc R U . . .
C47 C 0.3707(3) 0.1519(3) 0.8562(3) 0.0689(10) Uani 1 1 d . . . . .
C48 C 0.3539(4) 0.0722(4) 0.9759(3) 0.1208(19) Uani 1 1 d . . . . .
H48A H 0.4102 0.0880 1.0049 0.181 Uiso 1 1 calc R U . . .
H48B H 0.3640 -0.0037 0.9852 0.181 Uiso 1 1 calc R U . . .
H48C H 0.2768 0.0817 1.0132 0.181 Uiso 1 1 calc R U . . .
C49 C 0.4289(3) 0.2498(4) 0.8104(3) 0.0743(11) Uani 1 1 d . . . . .
H49 H 0.4634 0.2673 0.8526 0.089 Uiso 1 1 calc R U . . .
C50 C 0.4381(3) 0.3240(3) 0.7031(3) 0.0604(10) Uani 1 1 d . . . . .
H50 H 0.4780 0.3909 0.6741 0.073 Uiso 1 1 calc R U . . .
F1 F 0.08047(19) 0.04621(18) 0.56135(17) 0.0921(7) Uani 1 1 d . . . . .
N1 N 0.1829(2) 0.4278(2) 0.18233(19) 0.0419(6) Uani 1 1 d . . . . .
N2 N 0.4893(2) 0.28643(19) 0.16546(18) 0.0397(6) Uani 1 1 d . . . . .
O1 O 0.35055(18) 0.53220(17) 0.10412(16) 0.0510(6) Uani 1 1 d . . . . .
O2 O 0.17165(18) 0.39944(18) 0.47444(18) 0.0576(6) Uani 1 1 d . . . . .
O3 O 0.3718(2) 0.48352(17) 0.50413(17) 0.0558(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
C1 C2 1.377(6) . ?
C1 C6 1.382(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.361(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.507(4) . ?
C7 N1 1.464(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.214(3) . ?
C8 N1 1.367(4) . ?
C8 C9 1.543(4) . ?
C9 C33 1.499(4) . ?
C9 C10 1.516(4) . ?
C9 C16 1.587(4) . ?
C10 C11 1.378(4) . ?
C10 C15 1.385(4) . ?
C11 C12 1.378(4) . ?
C11 H11 0.9300 . ?
C12 F1 1.361(4) . ?
C12 C13 1.367(5) . ?
C13 C14 1.380(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(4) . ?
C14 H14 0.9300 . ?
C15 N1 1.414(4) . ?
C16 C42 1.518(4) . ?
C16 C17 1.531(4) . ?
C16 H16 0.9800 . ?
C17 O2 1.218(3) . ?
C17 C18 1.496(4) . ?
C18 C19 1.378(4) . ?
C18 C24 1.379(4) . ?
C19 C20 1.386(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(5) . ?
C20 H20 0.9300 . ?
C21 C23 1.387(5) . ?
C21 C22 1.518(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.380(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 N2 1.459(3) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.387(4) . ?
C26 N2 1.389(3) . ?
C26 C31 1.411(4) . ?
C27 C28 1.380(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.400(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.376(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.403(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.439(4) . ?
C32 C33 1.374(4) . ?
C32 C41 1.457(4) . ?
C33 N2 1.378(3) . ?
C34 C35 1.372(4) . ?
C34 C40 1.389(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.378(4) . ?
C35 H35 0.9300 . ?
C36 C38 1.384(4) . ?
C36 C37 1.522(4) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 C39 1.387(4) . ?
C38 H38 0.9300 . ?
C39 C40 1.387(4) . ?
C39 H39 0.9300 . ?
C40 C41 1.489(4) . ?
C41 C42 1.355(4) . ?
C42 C43 1.481(4) . ?
C43 O3 1.227(3) . ?
C43 C44 1.485(4) . ?
C44 C45 1.363(4) . ?
C44 C50 1.387(4) . ?
C45 C46 1.389(5) . ?
C45 H45 0.9300 . ?
C46 C47 1.385(5) . ?
C46 H46 0.9300 . ?
C47 C49 1.357(5) . ?
C47 C48 1.519(5) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 C50 1.376(5) . ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.9(4) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.1(5) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 120.5(5) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 121.1(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 117.8(3) . . ?
C5 C6 C7 120.5(3) . . ?
C1 C6 C7 121.7(3) . . ?
N1 C7 C6 112.8(2) . . ?
N1 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O1 C8 N1 126.1(3) . . ?
O1 C8 C9 126.1(3) . . ?
N1 C8 C9 107.8(2) . . ?
C33 C9 C10 114.0(2) . . ?
C33 C9 C8 113.8(2) . . ?
C10 C9 C8 102.1(2) . . ?
C33 C9 C16 106.7(2) . . ?
C10 C9 C16 113.2(2) . . ?
C8 C9 C16 106.9(2) . . ?
C11 C10 C15 120.6(3) . . ?
C11 C10 C9 130.3(3) . . ?
C15 C10 C9 108.9(2) . . ?
C10 C11 C12 116.5(3) . . ?
C10 C11 H11 121.7 . . ?
C12 C11 H11 121.7 . . ?
F1 C12 C13 118.8(3) . . ?
F1 C12 C11 117.7(3) . . ?
C13 C12 C11 123.6(3) . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 117.5(3) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C14 C15 C10 121.9(3) . . ?
C14 C15 N1 128.5(3) . . ?
C10 C15 N1 109.5(2) . . ?
C42 C16 C17 111.6(2) . . ?
C42 C16 C9 112.9(2) . . ?
C17 C16 C9 107.8(2) . . ?
C42 C16 H16 108.1 . . ?
C17 C16 H16 108.1 . . ?
C9 C16 H16 108.1 . . ?
O2 C17 C18 119.9(3) . . ?
O2 C17 C16 118.9(3) . . ?
C18 C17 C16 121.0(3) . . ?
C19 C18 C24 118.6(3) . . ?
C19 C18 C17 123.4(3) . . ?
C24 C18 C17 117.9(3) . . ?
C18 C19 C20 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C23 118.3(3) . . ?
C20 C21 C22 121.7(4) . . ?
C23 C21 C22 120.0(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C21 121.1(3) . . ?
C24 C23 H23 119.4 . . ?
C21 C23 H23 119.4 . . ?
C18 C24 C23 120.4(3) . . ?
C18 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 N2 127.9(3) . . ?
C27 C26 C31 123.1(3) . . ?
N2 C26 C31 108.8(2) . . ?
C28 C27 C26 117.1(3) . . ?
C28 C27 H27 121.5 . . ?
C26 C27 H27 121.5 . . ?
C27 C28 C29 121.2(3) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 H28 119.4 . . ?
C30 C29 C28 121.5(3) . . ?
C30 C29 H29 119.3 . . ?
C28 C29 H29 119.3 . . ?
C29 C30 C31 119.0(3) . . ?
C29 C30 H30 120.5 . . ?
C31 C30 H30 120.5 . . ?
C30 C31 C26 118.1(3) . . ?
C30 C31 C32 135.7(3) . . ?
C26 C31 C32 106.1(2) . . ?
C33 C32 C31 107.0(2) . . ?
C33 C32 C41 121.2(2) . . ?
C31 C32 C41 131.8(2) . . ?
C32 C33 N2 110.4(2) . . ?
C32 C33 C9 122.8(2) . . ?
N2 C33 C9 126.7(2) . . ?
C35 C34 C40 120.9(3) . . ?
C35 C34 H34 119.6 . . ?
C40 C34 H34 119.5 . . ?
C34 C35 C36 121.5(3) . . ?
C34 C35 H35 119.2 . . ?
C36 C35 H35 119.2 . . ?
C35 C36 C38 117.8(3) . . ?
C35 C36 C37 121.7(3) . . ?
C38 C36 C37 120.4(3) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 C39 121.3(3) . . ?
C36 C38 H38 119.4 . . ?
C39 C38 H38 119.4 . . ?
C40 C39 C38 120.4(3) . . ?
C40 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C39 C40 C34 118.1(3) . . ?
C39 C40 C41 122.4(3) . . ?
C34 C40 C41 119.5(2) . . ?
C42 C41 C32 118.6(2) . . ?
C42 C41 C40 125.2(2) . . ?
C32 C41 C40 116.1(2) . . ?
C41 C42 C43 123.6(2) . . ?
C41 C42 C16 120.5(2) . . ?
C43 C42 C16 114.9(2) . . ?
O3 C43 C42 118.6(3) . . ?
O3 C43 C44 119.7(2) . . ?
C42 C43 C44 121.7(2) . . ?
C45 C44 C50 118.0(3) . . ?
C45 C44 C43 121.8(3) . . ?
C50 C44 C43 120.0(3) . . ?
C44 C45 C46 121.3(3) . . ?
C44 C45 H45 119.3 . . ?
C46 C45 H45 119.3 . . ?
C47 C46 C45 120.2(4) . . ?
C47 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?
C49 C47 C46 118.3(3) . . ?
C49 C47 C48 122.3(4) . . ?
C46 C47 C48 119.3(4) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C47 C49 C50 121.7(3) . . ?
C47 C49 H49 119.2 . . ?
C50 C49 H49 119.2 . . ?
C49 C50 C44 120.5(3) . . ?
C49 C50 H50 119.7 . . ?
C44 C50 H50 119.7 . . ?
C8 N1 C15 111.5(2) . . ?
C8 N1 C7 122.1(2) . . ?
C15 N1 C7 126.4(2) . . ?
C33 N2 C26 107.6(2) . . ?
C33 N2 C25 128.4(2) . . ?
C26 N2 C25 123.9(2) . . ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_A2
_database_code_depnum_ccdc_archive 'CCDC 2077433'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan'
;Yangzhou University
China
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H20 N2 O3'
_chemical_formula_sum            'C25 H20 N2 O3'
_chemical_formula_weight         396.43

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   17.8914(19)
_cell_length_b                   5.5286(6)
_cell_length_c                   20.497(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.686(3)
_cell_angle_gamma                90
_cell_volume                     2025.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3543
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      21.08

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6594
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20401
_diffrn_reflns_av_unetI/netI     0.1353
_diffrn_reflns_av_R_equivalents  0.1054
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.339
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3920
_reflns_number_gt                1734
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0541P)²+0.7016P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3920
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1938
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_ref         0.1544
_refine_ls_wR_factor_gt          0.1172
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.07027(17) 1.2687(6) -0.00070(15) 0.0555(10) Uani 1 1 d . . . . .
H1A H 0.0358 1.2599 0.0337 0.083 Uiso 1 1 calc R U . . .
H1B H 0.0439 1.2423 -0.0419 0.083 Uiso 1 1 calc R U . . .
H1C H 0.0933 1.4256 -0.0006 0.083 Uiso 1 1 calc R U . . .
C2 C 0.18415(16) 1.0374(6) -0.03247(13) 0.0411(8) Uani 1 1 d . . . . .
C3 C 0.19824(17) 1.1507(7) -0.09127(14) 0.0543(10) Uani 1 1 d . . . . .
H3 H 0.1687 1.2783 -0.1070 0.065 Uiso 1 1 calc R U . . .
C4 C 0.25709(19) 1.0677(8) -0.12507(15) 0.0661(11) Uani 1 1 d . . . . .
H4 H 0.2682 1.1402 -0.1644 0.079 Uiso 1 1 calc R U . . .
C5 C 0.30044(19) 0.8765(8) -0.10130(16) 0.0709(12) Uani 1 1 d . . . . .
H5 H 0.3395 0.8209 -0.1257 0.085 Uiso 1 1 calc R U . . .
C6 C 0.28764(17) 0.7672(7) -0.04313(14) 0.0582(10) Uani 1 1 d . . . . .
H6 H 0.3180 0.6407 -0.0281 0.070 Uiso 1 1 calc R U . . .
C7 C 0.22861(15) 0.8466(6) -0.00634(13) 0.0424(8) Uani 1 1 d . . . . .
C8 C 0.19810(15) 0.7868(6) 0.05600(13) 0.0375(8) Uani 1 1 d . . . . .
C9 C 0.13698(16) 0.9352(6) 0.06135(14) 0.0420(8) Uani 1 1 d . . . . .
H9 H 0.1059 0.9332 0.0964 0.050 Uiso 1 1 calc R U . . .
C10 C 0.4051(2) 0.0046(8) 0.19065(17) 0.0746(12) Uani 1 1 d . . . . .
H10 H 0.3917 0.0378 0.2330 0.090 Uiso 1 1 calc R U . . .
C11 C 0.4581(2) -0.1703(9) 0.1803(2) 0.0896(15) Uani 1 1 d . . . . .
H11 H 0.4801 -0.2512 0.2160 0.108 Uiso 1 1 calc R U . . .
C12 C 0.47914(19) -0.2284(7) 0.1188(2) 0.0678(11) Uani 1 1 d . . . . .
C13 C 0.5378(2) -0.4193(8) 0.1077(2) 0.1040(16) Uani 1 1 d . . . . .
H13A H 0.5864 -0.3558 0.1197 0.156 Uiso 1 1 calc R U . . .
H13B H 0.5359 -0.4643 0.0624 0.156 Uiso 1 1 calc R U . . .
H13C H 0.5283 -0.5588 0.1339 0.156 Uiso 1 1 calc R U . . .
C14 C 0.4444(2) -0.1082(8) 0.0679(2) 0.0740(12) Uani 1 1 d . . . . .
H14 H 0.4566 -0.1476 0.0255 0.089 Uiso 1 1 calc R U . . .
C15 C 0.39146(18) 0.0714(7) 0.07705(16) 0.0608(10) Uani 1 1 d . . . . .
H15 H 0.3693 0.1511 0.0412 0.073 Uiso 1 1 calc R U . . .
C16 C 0.37175(15) 0.1313(6) 0.13929(15) 0.0452(9) Uani 1 1 d . . . . .
C17 C 0.31495(15) 0.3189(6) 0.15456(15) 0.0440(9) Uani 1 1 d . . . . .
C18 C 0.28233(16) 0.4697(6) 0.10194(14) 0.0457(9) Uani 1 1 d . . . . .
H18 H 0.3034 0.4592 0.0614 0.055 Uiso 1 1 calc R U . . .
C19 C 0.22435(15) 0.6223(6) 0.10731(13) 0.0379(8) Uani 1 1 d . . . . .
C20 C 0.18224(15) 0.6353(6) 0.16915(13) 0.0365(8) Uani 1 1 d . . . . .
C21 C 0.19395(17) 0.8232(6) 0.21192(14) 0.0531(10) Uani 1 1 d . . . . .
H21 H 0.2292 0.9411 0.2033 0.064 Uiso 1 1 calc R U . . .
C22 C 0.15413(18) 0.8393(7) 0.26757(14) 0.0544(10) Uani 1 1 d . . . . .
H22 H 0.1623 0.9672 0.2965 0.065 Uiso 1 1 calc R U . . .
C23 C 0.10260(15) 0.6655(6) 0.27977(13) 0.0397(8) Uani 1 1 d . . . . .
C24 C 0.08958(16) 0.4762(7) 0.23806(14) 0.0504(9) Uani 1 1 d . . . . .
H24 H 0.0544 0.3584 0.2471 0.060 Uiso 1 1 calc R U . . .
C25 C 0.12960(16) 0.4627(6) 0.18210(14) 0.0490(9) Uani 1 1 d . . . . .
H25 H 0.1208 0.3358 0.1530 0.059 Uiso 1 1 calc R U . . .
N1 N 0.12772(12) 1.0841(5) 0.00940(11) 0.0426(7) Uani 1 1 d . . . . .
N2 N 0.05958(16) 0.6774(7) 0.33904(13) 0.0568(8) Uani 1 1 d . . . . .
O1 O 0.29734(12) 0.3423(4) 0.21123(10) 0.0615(7) Uani 1 1 d . . . . .
O2 O 0.01520(14) 0.5172(6) 0.34900(11) 0.0778(9) Uani 1 1 d . . . . .
O3 O 0.06995(15) 0.8489(6) 0.37539(12) 0.0910(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.456(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.380(3) . ?
C2 C3 1.392(4) . ?
C2 C7 1.411(4) . ?
C3 C4 1.367(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.397(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.451(4) . ?
C8 C9 1.376(4) . ?
C8 C19 1.452(4) . ?
C9 N1 1.350(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(5) . ?
C10 C16 1.377(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(5) . ?
C11 H11 0.9300 . ?
C12 C14 1.363(5) . ?
C12 C13 1.513(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.392(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.495(4) . ?
C17 O1 1.225(3) . ?
C17 C18 1.463(4) . ?
C18 C19 1.346(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.506(4) . ?
C20 C21 1.369(4) . ?
C20 C25 1.375(4) . ?
C21 C22 1.376(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.363(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.364(4) . ?
C23 N2 1.470(4) . ?
C24 C25 1.382(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
N2 O2 1.213(4) . ?
N2 O3 1.215(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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 128.4(3) . . ?
N1 C2 C7 108.7(2) . . ?
C3 C2 C7 122.9(3) . . ?
C4 C3 C2 117.6(3) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 122.0(3) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C2 117.2(3) . . ?
C6 C7 C8 136.8(3) . . ?
C2 C7 C8 106.0(2) . . ?
C9 C8 C7 105.5(3) . . ?
C9 C8 C19 123.2(3) . . ?
C7 C8 C19 131.2(3) . . ?
N1 C9 C8 111.7(3) . . ?
N1 C9 H9 124.2 . . ?
C8 C9 H9 124.2 . . ?
C11 C10 C16 121.1(3) . . ?
C11 C10 H10 119.5 . . ?
C16 C10 H10 119.5 . . ?
C12 C11 C10 121.8(4) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C14 C12 C11 117.1(4) . . ?
C14 C12 C13 121.2(4) . . ?
C11 C12 C13 121.7(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C15 122.2(3) . . ?
C12 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C10 C16 C15 117.7(3) . . ?
C10 C16 C17 117.9(3) . . ?
C15 C16 C17 124.5(3) . . ?
O1 C17 C18 121.9(3) . . ?
O1 C17 C16 118.6(3) . . ?
C18 C17 C16 119.5(3) . . ?
C19 C18 C17 125.4(3) . . ?
C19 C18 H18 117.3 . . ?
C17 C18 H18 117.3 . . ?
C18 C19 C8 123.9(2) . . ?
C18 C19 C20 121.1(3) . . ?
C8 C19 C20 115.0(3) . . ?
C21 C20 C25 119.2(3) . . ?
C21 C20 C19 120.5(3) . . ?
C25 C20 C19 120.2(3) . . ?
C20 C21 C22 120.7(3) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 119.2(3) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C24 121.5(3) . . ?
C22 C23 N2 120.3(3) . . ?
C24 C23 N2 118.1(3) . . ?
C23 C24 C25 118.8(3) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?
C20 C25 C24 120.6(3) . . ?
C20 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C9 N1 C2 108.1(2) . . ?
C9 N1 C1 126.8(2) . . ?
C2 N1 C1 125.1(3) . . ?
O2 N2 O3 123.3(3) . . ?
O2 N2 C23 118.6(3) . . ?
O3 N2 C23 118.1(3) . . ?

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_5b
_database_code_depnum_ccdc_archive 'CCDC 2077432'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan'
;Yangzhou University
China
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H33 N3 O4'
_chemical_formula_sum            'C39 H33 N3 O4'
_chemical_formula_weight         607.68

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   12.362(4)
_cell_length_b                   14.904(4)
_cell_length_c                   18.652(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.489(9)
_cell_angle_gamma                90
_cell_volume                     3259.3(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5523
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      22.73

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6531
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15073
_diffrn_reflns_av_unetI/netI     0.0716
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.210
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             6274
_reflns_number_gt                3562
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+1.1252P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0090(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6274
_refine_ls_number_parameters     421
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3952(2) 0.58186(18) 0.38784(15) 0.0656(8) Uani 1 1 d . . . . .
H1A H 0.4293 0.5494 0.4340 0.098 Uiso 1 1 calc R U . . .
H1B H 0.3551 0.6331 0.3978 0.098 Uiso 1 1 calc R U . . .
H1C H 0.4537 0.6014 0.3677 0.098 Uiso 1 1 calc R U . . .
C2 C 0.2024(2) 0.51230(15) 0.32889(13) 0.0444(6) Uani 1 1 d . . . . .
C3 C 0.1445(2) 0.54749(17) 0.37563(14) 0.0568(7) Uani 1 1 d . . . . .
H3 H 0.1801 0.5869 0.4147 0.068 Uiso 1 1 calc R U . . .
C4 C 0.0332(2) 0.52189(19) 0.36190(15) 0.0647(8) Uani 1 1 d . . . . .
H4 H -0.0074 0.5440 0.3924 0.078 Uiso 1 1 calc R U . . .
C5 C -0.0199(2) 0.46346(17) 0.30323(15) 0.0580(7) Uani 1 1 d . . . . .
H5 H -0.0953 0.4470 0.2953 0.070 Uiso 1 1 calc R U . . .
C6 C 0.03653(19) 0.42964(15) 0.25683(13) 0.0471(6) Uani 1 1 d . . . . .
H6 H -0.0006 0.3911 0.2175 0.057 Uiso 1 1 calc R U . . .
C7 C 0.15035(18) 0.45351(14) 0.26889(12) 0.0390(5) Uani 1 1 d . . . . .
C8 C 0.23725(18) 0.42815(14) 0.23685(12) 0.0393(5) Uani 1 1 d . . . . .
C9 C 0.33543(18) 0.47023(15) 0.27879(13) 0.0420(6) Uani 1 1 d . . . . .
C10 C 0.09033(19) 0.25899(15) 0.09906(13) 0.0475(6) Uani 1 1 d . . . . .
H10 H 0.1394 0.2129 0.1226 0.057 Uiso 1 1 calc R U . . .
C11 C -0.0123(2) 0.23873(16) 0.04480(14) 0.0576(7) Uani 1 1 d . . . . .
H11 H -0.0300 0.1790 0.0319 0.069 Uiso 1 1 calc R U . . .
C12 C -0.0891(2) 0.30441(17) 0.00929(14) 0.0566(7) Uani 1 1 d . . . . .
C13 C -0.2006(3) 0.2815(2) -0.05034(18) 0.1005(12) Uani 1 1 d . . . . .
H13A H -0.1859 0.2471 -0.0897 0.151 Uiso 1 1 calc R U . . .
H13B H -0.2398 0.3358 -0.0712 0.151 Uiso 1 1 calc R U . . .
H13C H -0.2472 0.2471 -0.0279 0.151 Uiso 1 1 calc R U . . .
C14 C -0.0598(2) 0.39156(16) 0.03078(13) 0.0508(6) Uani 1 1 d . . . . .
H14 H -0.1103 0.4374 0.0085 0.061 Uiso 1 1 calc R U . . .
C15 C 0.04237(19) 0.41281(15) 0.08443(13) 0.0446(6) Uani 1 1 d . . . . .
H15 H 0.0591 0.4725 0.0980 0.054 Uiso 1 1 calc R U . . .
C16 C 0.12073(17) 0.34681(14) 0.11865(12) 0.0383(5) Uani 1 1 d . . . . .
C17 C 0.23401(18) 0.37166(14) 0.17228(12) 0.0389(5) Uani 1 1 d . . . . .
C18 C 0.33407(18) 0.34440(14) 0.16440(12) 0.0407(6) Uani 1 1 d . . . . .
C19 C 0.34143(19) 0.27812(15) 0.10650(13) 0.0448(6) Uani 1 1 d . . . . .
C20 C 0.28262(19) 0.29322(15) 0.02506(13) 0.0459(6) Uani 1 1 d . . . . .
C21 C 0.2635(3) 0.22163(17) -0.02452(16) 0.0687(8) Uani 1 1 d . . . . .
H21 H 0.2956 0.1661 -0.0073 0.082 Uiso 1 1 calc R U . . .
C22 C 0.1977(3) 0.2313(2) -0.09903(16) 0.0779(9) Uani 1 1 d . . . . .
H22 H 0.1853 0.1818 -0.1310 0.093 Uiso 1 1 calc R U . . .
C23 C 0.1501(2) 0.31224(18) -0.12726(14) 0.0596(7) Uani 1 1 d . . . . .
C24 C 0.0716(3) 0.3208(2) -0.20742(15) 0.0895(10) Uani 1 1 d . . . . .
H24A H 0.0352 0.2641 -0.2240 0.134 Uiso 1 1 calc R U . . .
H24B H 0.1149 0.3382 -0.2397 0.134 Uiso 1 1 calc R U . . .
H24C H 0.0146 0.3654 -0.2096 0.134 Uiso 1 1 calc R U . . .
C25 C 0.1758(2) 0.38511(17) -0.07919(14) 0.0564(7) Uani 1 1 d . . . . .
H25 H 0.1491 0.4416 -0.0978 0.068 Uiso 1 1 calc R U . . .
C26 C 0.2403(2) 0.37614(16) -0.00409(14) 0.0503(6) Uani 1 1 d . . . . .
H26 H 0.2554 0.4263 0.0272 0.060 Uiso 1 1 calc R U . . .
C27 C 0.6409(2) 0.3005(2) 0.24597(17) 0.0738(8) Uani 1 1 d . U . . .
H27 H 0.6363 0.2751 0.2905 0.089 Uiso 1 1 calc R U . . .
C28 C 0.7376(3) 0.2863(3) 0.2247(2) 0.0982(10) Uani 1 1 d . U . . .
H28 H 0.7973 0.2516 0.2548 0.118 Uiso 1 1 calc R U . . .
C29 C 0.7450(3) 0.3233(3) 0.1596(2) 0.1024(11) Uani 1 1 d . U . . .
H29 H 0.8099 0.3137 0.1456 0.123 Uiso 1 1 calc R U . . .
C30 C 0.6586(3) 0.3740(2) 0.1151(2) 0.0910(9) Uani 1 1 d . U . . .
H30 H 0.6644 0.3991 0.0708 0.109 Uiso 1 1 calc R U . . .
C31 C 0.5614(2) 0.38826(19) 0.13577(17) 0.0698(7) Uani 1 1 d . U . . .
H31 H 0.5022 0.4228 0.1049 0.084 Uiso 1 1 calc R U . . .
C32 C 0.5517(2) 0.35177(17) 0.20168(15) 0.0552(6) Uani 1 1 d . U . . .
C33 C 0.44624(18) 0.36538(15) 0.22541(13) 0.0446(6) Uani 1 1 d . . . . .
H33 H 0.4525 0.3214 0.2656 0.054 Uiso 1 1 calc R U . . .
C34 C 0.44768(18) 0.46112(15) 0.26402(13) 0.0435(6) Uani 1 1 d . . . . .
C35 C 0.4577(2) 0.53444(16) 0.21010(15) 0.0521(6) Uani 1 1 d . . . . .
C36 C 0.5769(3) 0.6374(2) 0.16632(18) 0.0880(10) Uani 1 1 d . . . . .
H36A H 0.6038 0.6054 0.1307 0.132 Uiso 1 1 calc R U . . .
H36B H 0.6315 0.6826 0.1908 0.132 Uiso 1 1 calc R U . . .
H36C H 0.5052 0.6654 0.1403 0.132 Uiso 1 1 calc R U . . .
C37 C 0.6564(2) 0.55813(18) 0.28571(18) 0.0626(8) Uani 1 1 d . . . . .
C38 C 0.7413(2) 0.4932(2) 0.41046(17) 0.0878(10) Uani 1 1 d . . . . .
H38A H 0.7918 0.4482 0.4024 0.132 Uiso 1 1 calc R U . . .
H38B H 0.7154 0.4756 0.4518 0.132 Uiso 1 1 calc R U . . .
H38C H 0.7810 0.5494 0.4221 0.132 Uiso 1 1 calc R U . . .
C39 C 0.5469(2) 0.45490(17) 0.33700(15) 0.0529(6) Uani 1 1 d . . . . .
N1 N 0.31545(16) 0.52348(12) 0.33318(11) 0.0469(5) Uani 1 1 d . . . . .
N2 N 0.64278(16) 0.50306(15) 0.34168(12) 0.0585(6) Uani 1 1 d . . . . .
N3 N 0.56189(18) 0.57450(13) 0.22321(13) 0.0572(6) Uani 1 1 d . . . . .
O1 O 0.39734(14) 0.20939(11) 0.12830(10) 0.0608(5) Uani 1 1 d . . . . .
O2 O 0.37740(16) 0.55455(12) 0.15556(11) 0.0751(6) Uani 1 1 d . . . . .
O3 O 0.74779(17) 0.59207(14) 0.29208(13) 0.0905(7) Uani 1 1 d . . . . .
O4 O 0.54219(15) 0.40669(14) 0.38820(11) 0.0737(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
C1 N1 1.460(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.384(3) . ?
C2 C3 1.394(3) . ?
C2 C7 1.406(3) . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.399(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.436(3) . ?
C8 C9 1.370(3) . ?
C8 C17 1.459(3) . ?
C9 N1 1.371(3) . ?
C9 C34 1.504(3) . ?
C10 C16 1.379(3) . ?
C10 C11 1.382(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(3) . ?
C11 H11 0.9300 . ?
C12 C14 1.374(3) . ?
C12 C13 1.511(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.377(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.487(3) . ?
C17 C18 1.354(3) . ?
C18 C19 1.488(3) . ?
C18 C33 1.521(3) . ?
C19 O1 1.231(3) . ?
C19 C20 1.478(3) . ?
C20 C21 1.382(3) . ?
C20 C26 1.384(3) . ?
C21 C22 1.377(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.372(4) . ?
C22 H22 0.9300 . ?
C23 C25 1.380(3) . ?
C23 C24 1.508(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.381(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C32 1.381(3) . ?
C27 C28 1.390(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.363(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.355(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.390(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.384(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.517(3) . ?
C33 C34 1.596(3) . ?
C33 H33 0.9800 . ?
C34 C35 1.517(3) . ?
C34 C39 1.519(3) . ?
C35 O2 1.212(3) . ?
C35 N3 1.370(3) . ?
C36 N3 1.471(3) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 O3 1.209(3) . ?
C37 N2 1.380(3) . ?
C37 N3 1.385(3) . ?
C38 N2 1.470(3) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 O4 1.211(3) . ?
C39 N2 1.365(3) . ?

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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 128.9(2) . . ?
N1 C2 C7 108.65(19) . . ?
C3 C2 C7 122.4(2) . . ?
C4 C3 C2 117.5(2) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 121.1(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 119.5(2) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C2 118.0(2) . . ?
C6 C7 C8 135.5(2) . . ?
C2 C7 C8 106.34(19) . . ?
C9 C8 C7 106.63(19) . . ?
C9 C8 C17 121.5(2) . . ?
C7 C8 C17 131.83(20) . . ?
C8 C9 N1 110.7(2) . . ?
C8 C9 C34 123.8(2) . . ?
N1 C9 C34 125.53(19) . . ?
C16 C10 C11 120.7(2) . . ?
C16 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 121.9(2) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C14 C12 C11 117.0(2) . . ?
C14 C12 C13 121.5(2) . . ?
C11 C12 C13 121.5(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C15 121.7(2) . . ?
C12 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C16 121.2(2) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C10 C16 C15 117.4(2) . . ?
C10 C16 C17 122.30(19) . . ?
C15 C16 C17 120.30(19) . . ?
C18 C17 C8 118.42(19) . . ?
C18 C17 C16 123.39(19) . . ?
C8 C17 C16 118.19(19) . . ?
C17 C18 C19 123.14(19) . . ?
C17 C18 C33 120.30(19) . . ?
C19 C18 C33 115.37(19) . . ?
O1 C19 C20 120.5(2) . . ?
O1 C19 C18 118.0(2) . . ?
C20 C19 C18 121.42(19) . . ?
C21 C20 C26 117.6(2) . . ?
C21 C20 C19 119.6(2) . . ?
C26 C20 C19 122.8(2) . . ?
C22 C21 C20 121.0(3) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C21 121.6(3) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C22 C23 C25 117.4(2) . . ?
C22 C23 C24 121.2(3) . . ?
C25 C23 C24 121.4(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 C26 121.5(2) . . ?
C23 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C25 C26 C20 120.6(2) . . ?
C25 C26 H26 119.7 . . ?
C20 C26 H26 119.7 . . ?
C32 C27 C28 120.6(3) . . ?
C32 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C29 C28 C27 120.0(3) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C30 C29 C28 120.5(3) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C31 119.9(3) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C32 C31 C30 120.9(3) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C27 C32 C31 118.1(3) . . ?
C27 C32 C33 119.8(2) . . ?
C31 C32 C33 122.1(2) . . ?
C32 C33 C18 114.70(19) . . ?
C32 C33 C34 111.31(18) . . ?
C18 C33 C34 113.48(17) . . ?
C32 C33 H33 105.5 . . ?
C18 C33 H33 105.5 . . ?
C34 C33 H33 105.5 . . ?
C9 C34 C35 109.28(18) . . ?
C9 C34 C39 111.8(2) . . ?
C35 C34 C39 115.2(2) . . ?
C9 C34 C33 106.53(17) . . ?
C35 C34 C33 109.68(19) . . ?
C39 C34 C33 103.90(18) . . ?
O2 C35 N3 121.0(2) . . ?
O2 C35 C34 121.2(2) . . ?
N3 C35 C34 117.7(2) . . ?
N3 C36 H36A 109.5 . . ?
N3 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N3 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O3 C37 N2 120.6(3) . . ?
O3 C37 N3 121.4(3) . . ?
N2 C37 N3 118.0(2) . . ?
N2 C38 H38A 109.5 . . ?
N2 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
N2 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O4 C39 N2 121.3(2) . . ?
O4 C39 C34 121.1(2) . . ?
N2 C39 C34 117.6(2) . . ?
C9 N1 C2 107.64(18) . . ?
C9 N1 C1 128.4(2) . . ?
C2 N1 C1 123.9(2) . . ?
C39 N2 C37 125.2(2) . . ?
C39 N2 C38 117.8(2) . . ?
C37 N2 C38 117.0(2) . . ?
C35 N3 C37 124.6(2) . . ?
C35 N3 C36 118.4(2) . . ?
C37 N3 C36 117.0(2) . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 2077431'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan'
;Yangzhou University
China
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C49 H37 Cl N2 O4'
_chemical_formula_sum            'C49 H37 Cl N2 O4'
_chemical_formula_weight         753.25

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.3059(11)
_cell_length_b                   12.9944(10)
_cell_length_c                   13.5855(11)
_cell_angle_alpha                99.021(2)
_cell_angle_beta                 99.217(3)
_cell_angle_gamma                110.717(3)
_cell_volume                     1951.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    5290
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      24.42

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             788
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.147
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27540
_diffrn_reflns_av_unetI/netI     0.1226
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.960
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             7613
_reflns_number_gt                3622
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0897P)²+0.4700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7613
_refine_ls_number_parameters     508
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1978
_refine_ls_R_factor_gt           0.0749
_refine_ls_wR_factor_ref         0.2031
_refine_ls_wR_factor_gt          0.1648
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0113(3) 0.1205(3) 0.6035(3) 0.0640(10) Uani 1 1 d . . . . .
H1A H 0.0692 0.1115 0.5670 0.096 Uiso 1 1 calc R U . . .
H1B H -0.0578 0.1158 0.5557 0.096 Uiso 1 1 calc R U . . .
H1C H -0.0116 0.0617 0.6401 0.096 Uiso 1 1 calc R U . . .
C2 C 0.0288(3) 0.2510(3) 0.7663(2) 0.0495(9) Uani 1 1 d . . . . .
C3 C -0.0656(4) 0.1825(4) 0.8006(3) 0.0753(12) Uani 1 1 d . . . . .
H3 H -0.1169 0.1112 0.7613 0.090 Uiso 1 1 calc R U . . .
C4 C -0.0803(4) 0.2241(4) 0.8946(3) 0.0893(14) Uani 1 1 d . . . . .
H4 H -0.1421 0.1794 0.9197 0.107 Uiso 1 1 calc R U . . .
C5 C -0.0064(4) 0.3298(4) 0.9526(3) 0.0792(13) Uani 1 1 d . . . . .
H5 H -0.0195 0.3549 1.0158 0.095 Uiso 1 1 calc R U . . .
C6 C 0.0866(3) 0.3995(3) 0.9195(2) 0.0588(10) Uani 1 1 d . . . . .
H6 H 0.1353 0.4713 0.9593 0.071 Uiso 1 1 calc R U . . .
C7 C 0.1068(3) 0.3599(3) 0.8239(2) 0.0463(8) Uani 1 1 d . . . . .
C8 C 0.1902(3) 0.4053(2) 0.7633(2) 0.0398(8) Uani 1 1 d . . . . .
C9 C 0.1578(3) 0.3241(2) 0.6742(2) 0.0390(8) Uani 1 1 d . . . . .
C10 C 0.3776(3) 0.5755(3) 0.9730(2) 0.0508(9) Uani 1 1 d . . . . .
H10 H 0.3905 0.5090 0.9716 0.061 Uiso 1 1 calc R U . . .
C11 C 0.4131(3) 0.6540(3) 1.0635(3) 0.0599(10) Uani 1 1 d . . . . .
H11 H 0.4532 0.6429 1.1224 0.072 Uiso 1 1 calc R U . . .
C12 C 0.3890(4) 0.7495(3) 1.0664(3) 0.0657(11) Uani 1 1 d . . . . .
C13 C 0.3316(4) 0.7675(3) 0.9795(3) 0.0707(12) Uani 1 1 d . . . . .
H13 H 0.3144 0.8319 0.9822 0.085 Uiso 1 1 calc R U . . .
C14 C 0.3002(3) 0.6896(3) 0.8890(2) 0.0561(10) Uani 1 1 d . . . . .
H14 H 0.2626 0.7024 0.8299 0.067 Uiso 1 1 calc R U . . .
C15 C 0.3227(3) 0.5925(3) 0.8833(2) 0.0418(8) Uani 1 1 d . . . . .
C16 C 0.2908(3) 0.5125(2) 0.7823(2) 0.0421(8) Uani 1 1 d . . . . .
C17 C 0.3476(3) 0.5400(2) 0.7069(2) 0.0465(9) Uani 1 1 d . . . . .
C18 C 0.4412(4) 0.6503(3) 0.7099(3) 0.0624(11) Uani 1 1 d . . . . .
C19 C 0.5336(3) 0.7222(3) 0.8014(3) 0.0550(9) Uani 1 1 d . . . . .
C20 C 0.5662(4) 0.8392(3) 0.8186(3) 0.0701(11) Uani 1 1 d . . . . .
H20 H 0.5288 0.8691 0.7726 0.084 Uiso 1 1 calc R U . . .
C21 C 0.6514(5) 0.9090(3) 0.9014(4) 0.0962(15) Uani 1 1 d . . . . .
H21 H 0.6735 0.9868 0.9112 0.115 Uiso 1 1 calc R U . . .
C22 C 0.7063(4) 0.8659(4) 0.9721(4) 0.1005(16) Uani 1 1 d . . . . .
C23 C 0.8241(8) 0.9013(6) 1.1419(7) 0.246(6) Uani 1 1 d . . . . .
H23A H 0.7566 0.8480 1.1584 0.369 Uiso 1 1 calc R U . . .
H23B H 0.8679 0.9625 1.2008 0.369 Uiso 1 1 calc R U . . .
H23C H 0.8750 0.8644 1.1220 0.369 Uiso 1 1 calc R U . . .
C24 C 0.6821(4) 0.7541(4) 0.9541(4) 0.0917(15) Uani 1 1 d . . . . .
H24 H 0.7239 0.7255 0.9981 0.110 Uiso 1 1 calc R U . . .
C25 C 0.5942(4) 0.6824(3) 0.8691(3) 0.0702(11) Uani 1 1 d . . . . .
H25 H 0.5759 0.6050 0.8578 0.084 Uiso 1 1 calc R U . . .
C26 C 0.3507(4) -0.0281(4) 0.4339(3) 0.0738(12) Uani 1 1 d . . . . .
H26 H 0.3763 -0.0073 0.3765 0.089 Uiso 1 1 calc R U . . .
C27 C 0.3001(5) -0.1416(4) 0.4354(5) 0.0989(16) Uani 1 1 d . . . . .
H27 H 0.2907 -0.1965 0.3782 0.119 Uiso 1 1 calc R U . . .
C28 C 0.2646(5) -0.1732(4) 0.5184(5) 0.1073(18) Uani 1 1 d . . . . .
H28 H 0.2324 -0.2495 0.5190 0.129 Uiso 1 1 calc R U . . .
C29 C 0.2756(5) -0.0944(4) 0.6007(4) 0.1037(16) Uani 1 1 d . . . . .
H29 H 0.2507 -0.1161 0.6580 0.124 Uiso 1 1 calc R U . . .
C30 C 0.3243(4) 0.0200(3) 0.5998(3) 0.0738(12) Uani 1 1 d . . . . .
H30 H 0.3304 0.0740 0.6565 0.089 Uiso 1 1 calc R U . . .
C31 C 0.3629(3) 0.0537(3) 0.5174(3) 0.0509(9) Uani 1 1 d . . . . .
C32 C 0.4195(3) 0.1776(3) 0.5217(3) 0.0572(10) Uani 1 1 d . . . . .
H32A H 0.4869 0.2131 0.5806 0.069 Uiso 1 1 calc R U . . .
H32B H 0.4495 0.1879 0.4607 0.069 Uiso 1 1 calc R U . . .
C33 C 0.3296(3) 0.2920(2) 0.6182(3) 0.0425(8) Uani 1 1 d . . . . .
C34 C 0.2293(3) 0.3366(2) 0.5937(2) 0.0381(8) Uani 1 1 d . . . . .
C35 C 0.1710(3) 0.2748(2) 0.4828(2) 0.0406(8) Uani 1 1 d . . . . .
C36 C 0.0735(3) 0.2739(3) 0.4161(2) 0.0496(9) Uani 1 1 d . . . . .
H36 H 0.0243 0.3070 0.4403 0.060 Uiso 1 1 calc R U . . .
C37 C 0.0489(4) 0.2231(3) 0.3124(3) 0.0594(10) Uani 1 1 d . . . . .
C38 C -0.0530(4) 0.2294(4) 0.2371(3) 0.0923(15) Uani 1 1 d . . . . .
H38A H -0.0237 0.2585 0.1816 0.138 Uiso 1 1 calc R U . . .
H38B H -0.0849 0.2785 0.2714 0.138 Uiso 1 1 calc R U . . .
H38C H -0.1146 0.1551 0.2107 0.138 Uiso 1 1 calc R U . . .
C39 C 0.1223(4) 0.1735(3) 0.2796(3) 0.0697(12) Uani 1 1 d . . . . .
H39 H 0.1070 0.1409 0.2102 0.084 Uiso 1 1 calc R U . . .
C40 C 0.2190(4) 0.1701(3) 0.3463(3) 0.0604(10) Uani 1 1 d . . . . .
H40 H 0.2664 0.1340 0.3231 0.073 Uiso 1 1 calc R U . . .
C41 C 0.2417(3) 0.2225(3) 0.4482(2) 0.0448(8) Uani 1 1 d . . . . .
C42 C 0.2968(3) 0.4662(2) 0.5988(2) 0.0464(8) Uani 1 1 d . . . . .
H42 H 0.3642 0.4734 0.5667 0.056 Uiso 1 1 calc R U . . .
C43 C 0.2188(3) 0.5144(3) 0.5393(2) 0.0511(9) Uani 1 1 d . . . . .
C44 C 0.2238(3) 0.5249(3) 0.4313(2) 0.0494(9) Uani 1 1 d . . . . .
C45 C 0.3182(4) 0.5274(3) 0.3910(3) 0.0665(11) Uani 1 1 d . . . . .
H45 H 0.3839 0.5215 0.4306 0.080 Uiso 1 1 calc R U . . .
C46 C 0.3176(4) 0.5386(4) 0.2914(3) 0.0838(13) Uani 1 1 d . . . . .
H46 H 0.3834 0.5417 0.2646 0.101 Uiso 1 1 calc R U . . .
C47 C 0.2212(5) 0.5452(4) 0.2326(3) 0.0850(14) Uani 1 1 d . . . . .
H47 H 0.2198 0.5507 0.1650 0.102 Uiso 1 1 calc R U . . .
C48 C 0.1266(4) 0.5439(3) 0.2732(3) 0.0788(13) Uani 1 1 d . . . . .
H48 H 0.0608 0.5496 0.2336 0.095 Uiso 1 1 calc R U . . .
C49 C 0.1283(4) 0.5342(3) 0.3728(3) 0.0626(10) Uani 1 1 d . . . . .
H49 H 0.0638 0.5340 0.4004 0.075 Uiso 1 1 calc R U . . .
Cl1 Cl 0.43326(15) 0.84961(11) 1.18103(8) 0.1210(6) Uani 1 1 d . . . . .
N1 N 0.0629(2) 0.2302(2) 0.67561(19) 0.0463(7) Uani 1 1 d . . . . .
N2 N 0.3351(2) 0.2335(2) 0.5292(2) 0.0464(7) Uani 1 1 d . . . . .
O1 O 0.4411(3) 0.6817(2) 0.6291(2) 0.1074(12) Uani 1 1 d . . . . .
O2 O 0.7836(4) 0.9445(3) 1.0593(3) 0.169(2) Uani 1 1 d . . . . .
O3 O 0.3919(2) 0.3073(2) 0.70255(18) 0.0621(7) Uani 1 1 d . . . . .
O4 O 0.1487(2) 0.5422(2) 0.58001(18) 0.0704(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.455(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.381(4) . ?
C2 C3 1.390(5) . ?
C2 C7 1.410(5) . ?
C3 C4 1.372(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.414(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.439(4) . ?
C8 C9 1.372(4) . ?
C8 C16 1.452(4) . ?
C9 N1 1.364(4) . ?
C9 C34 1.503(4) . ?
C10 C11 1.365(4) . ?
C10 C15 1.385(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(5) . ?
C12 Cl1 1.734(3) . ?
C13 C14 1.366(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.486(4) . ?
C16 C17 1.354(4) . ?
C17 C18 1.477(5) . ?
C17 C42 1.519(4) . ?
C18 O1 1.230(4) . ?
C18 C19 1.464(5) . ?
C19 C25 1.369(5) . ?
C19 C20 1.398(5) . ?
C20 C21 1.347(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.387(6) . ?
C21 H21 0.9300 . ?
C22 C24 1.348(6) . ?
C22 O2 1.387(5) . ?
C23 O2 1.427(7) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.386(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C31 1.377(5) . ?
C26 C27 1.388(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.345(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.345(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.395(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.359(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.498(5) . ?
C32 N2 1.470(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 O3 1.216(3) . ?
C33 N2 1.349(4) . ?
C33 C34 1.551(4) . ?
C34 C35 1.514(4) . ?
C34 C42 1.576(4) . ?
C35 C41 1.375(4) . ?
C35 C36 1.378(4) . ?
C36 C37 1.394(4) . ?
C36 H36 0.9300 . ?
C37 C39 1.371(5) . ?
C37 C38 1.521(5) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.394(5) . ?
C39 H39 0.9300 . ?
C40 C41 1.379(4) . ?
C40 H40 0.9300 . ?
C41 N2 1.408(4) . ?
C42 C43 1.518(5) . ?
C42 H42 0.9800 . ?
C43 O4 1.220(4) . ?
C43 C44 1.504(4) . ?
C44 C45 1.354(5) . ?
C44 C49 1.363(5) . ?
C45 C46 1.384(5) . ?
C45 H45 0.9300 . ?
C46 C47 1.357(6) . ?
C46 H46 0.9300 . ?
C47 C48 1.361(6) . ?
C47 H47 0.9300 . ?
C48 C49 1.376(5) . ?
C48 H48 0.9300 . ?
C49 H49 0.9300 . ?

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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 129.2(3) . . ?
N1 C2 C7 108.5(3) . . ?
C3 C2 C7 122.3(3) . . ?
C4 C3 C2 117.5(4) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C5 C4 C3 121.9(4) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 121.6(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C7 118.8(4) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C2 C7 C6 118.0(3) . . ?
C2 C7 C8 106.3(3) . . ?
C6 C7 C8 135.7(3) . . ?
C9 C8 C7 106.3(3) . . ?
C9 C8 C16 122.0(3) . . ?
C7 C8 C16 131.8(3) . . ?
N1 C9 C8 110.9(3) . . ?
N1 C9 C34 126.4(3) . . ?
C8 C9 C34 122.3(3) . . ?
C11 C10 C15 121.5(3) . . ?
C11 C10 H10 119.2 . . ?
C15 C10 H10 119.2 . . ?
C10 C11 C12 119.1(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 Cl1 119.5(3) . . ?
C13 C12 Cl1 119.6(3) . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 121.6(3) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C10 117.7(3) . . ?
C14 C15 C16 119.5(3) . . ?
C10 C15 C16 122.8(3) . . ?
C17 C16 C8 120.0(3) . . ?
C17 C16 C15 122.0(3) . . ?
C8 C16 C15 117.9(3) . . ?
C16 C17 C18 126.5(3) . . ?
C16 C17 C42 120.1(3) . . ?
C18 C17 C42 111.9(3) . . ?
O1 C18 C19 118.8(3) . . ?
O1 C18 C17 116.9(3) . . ?
C19 C18 C17 124.3(3) . . ?
C25 C19 C20 117.6(4) . . ?
C25 C19 C18 124.0(3) . . ?
C20 C19 C18 118.3(3) . . ?
C21 C20 C19 120.5(4) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.6(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C24 C22 C21 120.0(4) . . ?
C24 C22 O2 124.5(5) . . ?
C21 C22 O2 115.5(4) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 C25 119.1(4) . . ?
C22 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C19 C25 C24 121.9(4) . . ?
C19 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C31 C26 C27 119.9(4) . . ?
C31 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C28 C27 C26 120.9(5) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C29 119.9(5) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C30 119.9(5) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C31 C30 C29 121.0(4) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C30 C31 C26 118.3(4) . . ?
C30 C31 C32 119.1(3) . . ?
C26 C31 C32 122.6(3) . . ?
N2 C32 C31 112.2(3) . . ?
N2 C32 H32A 109.2 . . ?
C31 C32 H32A 109.2 . . ?
N2 C32 H32B 109.2 . . ?
C31 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?
O3 C33 N2 126.4(3) . . ?
O3 C33 C34 126.1(3) . . ?
N2 C33 C34 107.6(3) . . ?
C9 C34 C35 120.8(3) . . ?
C9 C34 C33 110.0(2) . . ?
C35 C34 C33 101.7(2) . . ?
C9 C34 C42 109.2(2) . . ?
C35 C34 C42 108.9(2) . . ?
C33 C34 C42 105.0(2) . . ?
C41 C35 C36 120.3(3) . . ?
C41 C35 C34 108.0(3) . . ?
C36 C35 C34 131.4(3) . . ?
C35 C36 C37 119.9(3) . . ?
C35 C36 H36 120.1 . . ?
C37 C36 H36 120.1 . . ?
C39 C37 C36 118.6(3) . . ?
C39 C37 C38 121.2(4) . . ?
C36 C37 C38 120.1(4) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 C40 122.5(3) . . ?
C37 C39 H39 118.7 . . ?
C40 C39 H39 118.7 . . ?
C41 C40 C39 117.3(4) . . ?
C41 C40 H40 121.4 . . ?
C39 C40 H40 121.4 . . ?
C35 C41 C40 121.4(3) . . ?
C35 C41 N2 110.5(3) . . ?
C40 C41 N2 128.1(3) . . ?
C43 C42 C17 108.0(3) . . ?
C43 C42 C34 112.4(3) . . ?
C17 C42 C34 114.2(2) . . ?
C43 C42 H42 107.3 . . ?
C17 C42 H42 107.3 . . ?
C34 C42 H42 107.3 . . ?
O4 C43 C44 120.0(3) . . ?
O4 C43 C42 118.6(3) . . ?
C44 C43 C42 121.4(3) . . ?
C45 C44 C49 119.3(3) . . ?
C45 C44 C43 123.4(3) . . ?
C49 C44 C43 117.3(3) . . ?
C44 C45 C46 120.4(4) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C47 C46 C45 120.1(4) . . ?
C47 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?
C46 C47 C48 119.7(4) . . ?
C46 C47 H47 120.2 . . ?
C48 C47 H47 120.2 . . ?
C47 C48 C49 120.0(4) . . ?
C47 C48 H48 120.0 . . ?
C49 C48 H48 120.0 . . ?
C44 C49 C48 120.5(4) . . ?
C44 C49 H49 119.7 . . ?
C48 C49 H49 119.7 . . ?
C9 N1 C2 108.0(3) . . ?
C9 N1 C1 128.5(3) . . ?
C2 N1 C1 123.2(3) . . ?
C33 N2 C41 111.2(3) . . ?
C33 N2 C32 123.5(3) . . ?
C41 N2 C32 124.9(3) . . ?
C22 O2 C23 116.9(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
N1 C2 C3 C4 -179.7(4) . . . . ?
C7 C2 C3 C4 -0.8(6) . . . . ?
C2 C3 C4 C5 1.0(7) . . . . ?
C3 C4 C5 C6 -0.2(7) . . . . ?
C4 C5 C6 C7 -0.8(6) . . . . ?
N1 C2 C7 C6 178.9(3) . . . . ?
C3 C2 C7 C6 -0.1(5) . . . . ?
N1 C2 C7 C8 0.4(4) . . . . ?
C3 C2 C7 C8 -178.7(3) . . . . ?
C5 C6 C7 C2 1.0(5) . . . . ?
C5 C6 C7 C8 179.0(4) . . . . ?
C2 C7 C8 C9 0.8(3) . . . . ?
C6 C7 C8 C9 -177.3(3) . . . . ?
C2 C7 C8 C16 -179.4(3) . . . . ?
C6 C7 C8 C16 2.4(6) . . . . ?
C7 C8 C9 N1 -1.8(3) . . . . ?
C16 C8 C9 N1 178.5(3) . . . . ?
C7 C8 C9 C34 -175.6(3) . . . . ?
C16 C8 C9 C34 4.6(4) . . . . ?
C15 C10 C11 C12 3.0(6) . . . . ?
C10 C11 C12 C13 -1.1(6) . . . . ?
C10 C11 C12 Cl1 179.8(3) . . . . ?
C11 C12 C13 C14 -1.0(6) . . . . ?
Cl1 C12 C13 C14 178.2(3) . . . . ?
C12 C13 C14 C15 1.2(6) . . . . ?
C13 C14 C15 C10 0.7(5) . . . . ?
C13 C14 C15 C16 -177.7(3) . . . . ?
C11 C10 C15 C14 -2.8(5) . . . . ?
C11 C10 C15 C16 175.5(3) . . . . ?
C9 C8 C16 C17 7.3(4) . . . . ?
C7 C8 C16 C17 -172.4(3) . . . . ?
C9 C8 C16 C15 -176.9(3) . . . . ?
C7 C8 C16 C15 3.4(5) . . . . ?
C14 C15 C16 C17 67.3(4) . . . . ?
C10 C15 C16 C17 -111.0(4) . . . . ?
C14 C15 C16 C8 -108.4(3) . . . . ?
C10 C15 C16 C8 73.3(4) . . . . ?
C8 C16 C17 C18 172.2(3) . . . . ?
C15 C16 C17 C18 -3.5(5) . . . . ?
C8 C16 C17 C42 7.8(5) . . . . ?
C15 C16 C17 C42 -167.8(3) . . . . ?
C16 C17 C18 O1 -144.4(4) . . . . ?
C42 C17 C18 O1 21.0(5) . . . . ?
C16 C17 C18 C19 36.7(6) . . . . ?
C42 C17 C18 C19 -157.9(3) . . . . ?
O1 C18 C19 C25 -136.9(4) . . . . ?
C17 C18 C19 C25 41.9(6) . . . . ?
O1 C18 C19 C20 40.0(6) . . . . ?
C17 C18 C19 C20 -141.1(4) . . . . ?
C25 C19 C20 C21 -2.4(6) . . . . ?
C18 C19 C20 C21 -179.6(4) . . . . ?
C19 C20 C21 C22 -1.4(7) . . . . ?
C20 C21 C22 C24 5.7(8) . . . . ?
C20 C21 C22 O2 -173.7(5) . . . . ?
C21 C22 C24 C25 -5.8(8) . . . . ?
O2 C22 C24 C25 173.5(5) . . . . ?
C20 C19 C25 C24 2.2(6) . . . . ?
C18 C19 C25 C24 179.2(4) . . . . ?
C22 C24 C25 C19 1.9(7) . . . . ?
C31 C26 C27 C28 -1.2(7) . . . . ?
C26 C27 C28 C29 1.4(8) . . . . ?
C27 C28 C29 C30 -0.3(8) . . . . ?
C28 C29 C30 C31 -1.0(7) . . . . ?
C29 C30 C31 C26 1.2(6) . . . . ?
C29 C30 C31 C32 -177.3(4) . . . . ?
C27 C26 C31 C30 -0.1(6) . . . . ?
C27 C26 C31 C32 178.4(4) . . . . ?
C30 C31 C32 N2 -64.7(4) . . . . ?
C26 C31 C32 N2 116.8(4) . . . . ?
N1 C9 C34 C35 32.1(4) . . . . ?
C8 C9 C34 C35 -155.1(3) . . . . ?
N1 C9 C34 C33 -85.8(3) . . . . ?
C8 C9 C34 C33 87.1(3) . . . . ?
N1 C9 C34 C42 159.5(3) . . . . ?
C8 C9 C34 C42 -27.6(4) . . . . ?
O3 C33 C34 C9 -41.4(4) . . . . ?
N2 C33 C34 C9 138.7(3) . . . . ?
O3 C33 C34 C35 -170.5(3) . . . . ?
N2 C33 C34 C35 9.6(3) . . . . ?
O3 C33 C34 C42 75.9(4) . . . . ?
N2 C33 C34 C42 -103.9(3) . . . . ?
C9 C34 C35 C41 -131.5(3) . . . . ?
C33 C34 C35 C41 -9.5(3) . . . . ?
C42 C34 C35 C41 101.0(3) . . . . ?
C9 C34 C35 C36 55.6(4) . . . . ?
C33 C34 C35 C36 177.5(3) . . . . ?
C42 C34 C35 C36 -72.0(4) . . . . ?
C41 C35 C36 C37 -2.2(5) . . . . ?
C34 C35 C36 C37 170.0(3) . . . . ?
C35 C36 C37 C39 0.9(5) . . . . ?
C35 C36 C37 C38 -175.4(3) . . . . ?
C36 C37 C39 C40 1.3(6) . . . . ?
C38 C37 C39 C40 177.6(3) . . . . ?
C37 C39 C40 C41 -2.1(5) . . . . ?
C36 C35 C41 C40 1.4(5) . . . . ?
C34 C35 C41 C40 -172.5(3) . . . . ?
C36 C35 C41 N2 -179.6(3) . . . . ?
C34 C35 C41 N2 6.5(3) . . . . ?
C39 C40 C41 C35 0.8(5) . . . . ?
C39 C40 C41 N2 -178.0(3) . . . . ?
C16 C17 C42 C43 93.6(3) . . . . ?
C18 C17 C42 C43 -72.8(4) . . . . ?
C16 C17 C42 C34 -32.3(4) . . . . ?
C18 C17 C42 C34 161.2(3) . . . . ?
C9 C34 C42 C43 -84.0(3) . . . . ?
C35 C34 C42 C43 49.9(3) . . . . ?
C33 C34 C42 C43 158.2(3) . . . . ?
C9 C34 C42 C17 39.7(4) . . . . ?
C35 C34 C42 C17 173.5(3) . . . . ?
C33 C34 C42 C17 -78.2(3) . . . . ?
C17 C42 C43 O4 -45.4(4) . . . . ?
C34 C42 C43 O4 81.6(4) . . . . ?
C17 C42 C43 C44 136.6(3) . . . . ?
C34 C42 C43 C44 -96.4(4) . . . . ?
O4 C43 C44 C45 160.5(4) . . . . ?
C42 C43 C44 C45 -21.5(5) . . . . ?
O4 C43 C44 C49 -18.3(5) . . . . ?
C42 C43 C44 C49 159.8(3) . . . . ?
C49 C44 C45 C46 -0.4(6) . . . . ?
C43 C44 C45 C46 -179.1(4) . . . . ?
C44 C45 C46 C47 -1.2(7) . . . . ?
C45 C46 C47 C48 1.8(7) . . . . ?
C46 C47 C48 C49 -1.0(7) . . . . ?
C45 C44 C49 C48 1.2(5) . . . . ?
C43 C44 C49 C48 -179.9(3) . . . . ?
C47 C48 C49 C44 -0.6(6) . . . . ?
C8 C9 N1 C2 2.0(3) . . . . ?
C34 C9 N1 C2 175.6(3) . . . . ?
C8 C9 N1 C1 -171.1(3) . . . . ?
C34 C9 N1 C1 2.4(5) . . . . ?
C3 C2 N1 C9 177.5(4) . . . . ?
C7 C2 N1 C9 -1.4(3) . . . . ?
C3 C2 N1 C1 -8.9(5) . . . . ?
C7 C2 N1 C1 172.1(3) . . . . ?
O3 C33 N2 C41 173.7(3) . . . . ?
C34 C33 N2 C41 -6.4(3) . . . . ?
O3 C33 N2 C32 0.5(5) . . . . ?
C34 C33 N2 C32 -179.6(3) . . . . ?
C35 C41 N2 C33 0.0(4) . . . . ?
C40 C41 N2 C33 179.0(3) . . . . ?
C35 C41 N2 C32 173.2(3) . . . . ?
C40 C41 N2 C32 -7.9(5) . . . . ?
C31 C32 N2 C33 98.5(4) . . . . ?
C31 C32 N2 C41 -73.8(4) . . . . ?
C24 C22 O2 C23 -10.8(10) . . . . ?
C21 C22 O2 C23 168.5(7) . . . . ?

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.045

