# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
# 
# 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. 
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data_mjp_kd_ad00128_0m
_database_code_depnum_ccdc_archive 'CCDC 2373295'
loop_
_audit_author_name
_audit_author_address
'Milosz Pawlicki'
;Faculty of Chemistry, Jagiellonian University
Poland
;
_audit_update_record             
;
2024-07-24 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_audit_creation_date             2024-04-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
''
krzysztof.dzieszkowski@uj.edu.pl
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H16 N2 O4'
_chemical_formula_sum            'C28 H16 N2 O4'
_chemical_formula_weight         444.43
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.6584(3)
_cell_length_b                   16.7506(6)
_cell_length_c                   16.0779(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.8020(10)
_cell_angle_gamma                90
_cell_volume                     2011.25(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0449 before and 0.0356 after correction.
The Ratio of minimum to maximum transmission is 0.8385.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             920
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'slow evaporation from DCM/hexane mixture'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9321
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         2.598
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'D8Quest Eco Photon50'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_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                3547
_reflns_number_total             4272
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.117
_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)+(0.0445P)²+1.4461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1222
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C81(H81), C16(H16), C10(H10), C61(H61), C131(H131), C17(H17), C72(H72),
 C141(H141), C19(H19), C3(H3), C62(H62), C4(H4), C71(H71), C142(H142),
 C132(H132)
;
_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
O3 O 0.06637(16) 0.33293(7) 0.49433(8) 0.0176(3) Uani 1 1 d . . . . .
O2 O 0.28033(18) 0.55171(8) 0.22334(8) 0.0237(3) Uani 1 1 d . . . . .
O4 O 0.0020(2) 0.27318(8) 0.32916(9) 0.0320(4) Uani 1 1 d . . . . .
N1 N 0.3192(2) 0.56480(9) 0.36846(9) 0.0178(3) Uani 1 1 d . . . . .
N2 N 0.15527(19) 0.41452(9) 0.61055(9) 0.0166(3) Uani 1 1 d . . . . .
C81 C 0.3641(2) 0.60490(10) 0.59249(11) 0.0175(4) Uani 1 1 d . . . . .
H81 H 0.410855 0.647059 0.630446 0.021 Uiso 1 1 calc R U . . .
C15 C 0.0710(2) 0.34516(10) 0.57774(11) 0.0167(4) Uani 1 1 d . . . . .
C16 C -0.0129(2) 0.28387(11) 0.61073(12) 0.0192(4) Uani 1 1 d . . . . .
H16 H -0.026887 0.278204 0.667694 0.023 Uiso 1 1 calc R U . . .
C7 C 0.4399(2) 0.66726(10) 0.45710(11) 0.0178(4) Uani 1 1 d . . . . .
C10 C 0.2174(2) 0.47878(10) 0.47742(11) 0.0171(4) Uani 1 1 d . . . . .
H10 H 0.166693 0.437586 0.438975 0.021 Uiso 1 1 calc R U . . .
C9 C 0.2960(2) 0.54591(10) 0.45113(11) 0.0169(4) Uani 1 1 d . . . . .
C11 C 0.2177(2) 0.47573(10) 0.56369(11) 0.0171(4) Uani 1 1 d . . . . .
C18 C -0.0245(2) 0.26205(10) 0.47216(12) 0.0191(4) Uani 1 1 d . . . . .
C61 C 0.4631(2) 0.68327(11) 0.30904(12) 0.0212(4) Uani 1 1 d . . . . .
H61 H 0.443126 0.664377 0.251999 0.025 Uiso 1 1 calc R U . . .
C13 C 0.2703(2) 0.51335(11) 0.70495(11) 0.0186(4) Uani 1 1 d . . . . .
C5 C 0.2664(2) 0.51707(11) 0.29740(11) 0.0194(4) Uani 1 1 d . . . . .
C12 C 0.2884(2) 0.53757(10) 0.62092(11) 0.0173(4) Uani 1 1 d . . . . .
C131 C 0.3186(3) 0.54963(12) 0.78427(12) 0.0239(4) Uani 1 1 d . . . . .
H131 H 0.368758 0.601747 0.789581 0.029 Uiso 1 1 calc R U . . .
C17 C -0.0737(2) 0.23132(11) 0.54177(12) 0.0195(4) Uani 1 1 d . . . . .
H17 H -0.137669 0.183014 0.543685 0.023 Uiso 1 1 calc R U . . .
C6 C 0.4088(2) 0.63953(11) 0.37270(12) 0.0187(4) Uani 1 1 d . . . . .
C14 C 0.1919(2) 0.43742(11) 0.69752(11) 0.0186(4) Uani 1 1 d . . . . .
C8 C 0.3689(2) 0.60842(10) 0.50682(12) 0.0175(4) Uani 1 1 d . . . . .
C72 C 0.5758(2) 0.78458(11) 0.41599(13) 0.0241(4) Uani 1 1 d . . . . .
H72 H 0.631856 0.834959 0.429515 0.029 Uiso 1 1 calc R U . . .
C141 C 0.1657(3) 0.39552(11) 0.76856(12) 0.0220(4) Uani 1 1 d . . . . .
H141 H 0.113528 0.343786 0.763333 0.026 Uiso 1 1 calc R U . . .
C19 C -0.0525(3) 0.23749(11) 0.38494(12) 0.0241(4) Uani 1 1 d . . . . .
H19 H -0.118550 0.189773 0.369044 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1719(3) 0.42849(13) 0.19585(12) 0.0268(4) Uani 1 1 d . . . . .
H3 H 0.125496 0.381258 0.166337 0.032 Uiso 1 1 calc R U . . .
C62 C 0.5475(3) 0.75561(11) 0.33289(13) 0.0247(4) Uani 1 1 d . . . . .
H62 H 0.587320 0.786456 0.291100 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2006(3) 0.44109(12) 0.28397(13) 0.0255(4) Uani 1 1 d . . . . .
H4 H 0.179006 0.404504 0.325709 0.031 Uiso 1 1 calc R U . . .
C71 C 0.5230(2) 0.74070(11) 0.47896(12) 0.0215(4) Uani 1 1 d . . . . .
H71 H 0.542902 0.760130 0.535800 0.026 Uiso 1 1 calc R U . . .
C142 C 0.2188(3) 0.43242(13) 0.84703(12) 0.0278(4) Uani 1 1 d . . . . .
H142 H 0.204518 0.404818 0.896707 0.033 Uiso 1 1 calc R U . . .
C2 C 0.2219(3) 0.49555(12) 0.16012(12) 0.0266(4) Uani 1 1 d . . . . .
C132 C 0.2930(3) 0.50908(12) 0.85560(12) 0.0276(4) Uani 1 1 d . . . . .
H132 H 0.325716 0.533269 0.910291 0.033 Uiso 1 1 calc R U . . .
C1 C 0.2274(3) 0.51641(14) 0.07462(14) 0.0359(5) Uani 1 1 d . . . . .
O1 O 0.2782(3) 0.58024(10) 0.05132(10) 0.0499(5) Uani 1 1 d . . . . .
H1 H 0.177(3) 0.4717(13) 0.0343(13) 0.025(5) Uiso 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
O3 C15 1.349(2) . ?
O3 C18 1.382(2) . ?
O2 C5 1.350(2) . ?
O2 C2 1.384(2) . ?
O4 C19 1.226(2) . ?
N1 C9 1.415(2) . ?
N1 C5 1.380(2) . ?
N1 C6 1.422(2) . ?
N2 C15 1.376(2) . ?
N2 C11 1.417(2) . ?
N2 C14 1.417(2) . ?
C81 H81 0.9500 . ?
C81 C12 1.391(2) . ?
C81 C8 1.387(3) . ?
C15 C16 1.378(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.411(3) . ?
C7 C6 1.404(3) . ?
C7 C8 1.449(2) . ?
C7 C71 1.394(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.385(2) . ?
C10 C11 1.388(2) . ?
C9 C8 1.410(2) . ?
C11 C12 1.411(2) . ?
C18 C17 1.359(3) . ?
C18 C19 1.431(3) . ?
C61 H61 0.9500 . ?
C61 C6 1.395(3) . ?
C61 C62 1.387(3) . ?
C13 C12 1.447(2) . ?
C13 C131 1.387(3) . ?
C13 C14 1.400(3) . ?
C5 C4 1.368(3) . ?
C131 H131 0.9500 . ?
C131 C132 1.384(3) . ?
C17 H17 0.9500 . ?
C14 C141 1.392(3) . ?
C72 H72 0.9500 . ?
C72 C62 1.393(3) . ?
C72 C71 1.382(3) . ?
C141 H141 0.9500 . ?
C141 C142 1.383(3) . ?
C19 H19 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.401(3) . ?
C3 C2 1.355(3) . ?
C62 H62 0.9500 . ?
C4 H4 0.9500 . ?
C71 H71 0.9500 . ?
C142 H142 0.9500 . ?
C142 C132 1.398(3) . ?
C2 C1 1.428(3) . ?
C132 H132 0.9500 . ?
C1 O1 1.225(3) . ?
C1 H1 1.01(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O3 C18 106.71(13) . . ?
C5 O2 C2 106.24(15) . . ?
C9 N1 C6 108.16(14) . . ?
C5 N1 C9 124.99(15) . . ?
C5 N1 C6 126.84(15) . . ?
C15 N2 C11 126.30(15) . . ?
C15 N2 C14 125.47(15) . . ?
C11 N2 C14 108.22(14) . . ?
C12 C81 H81 121.1 . . ?
C8 C81 H81 121.1 . . ?
C8 C81 C12 117.73(16) . . ?
O3 C15 N2 114.59(15) . . ?
O3 C15 C16 110.95(15) . . ?
N2 C15 C16 134.46(17) . . ?
C15 C16 H16 127.4 . . ?
C15 C16 C17 105.24(16) . . ?
C17 C16 H16 127.4 . . ?
C6 C7 C8 107.73(16) . . ?
C71 C7 C6 120.38(17) . . ?
C71 C7 C8 131.88(17) . . ?
C9 C10 H10 122.3 . . ?
C9 C10 C11 115.49(16) . . ?
C11 C10 H10 122.3 . . ?
C10 C9 N1 128.44(16) . . ?
C10 C9 C8 123.15(16) . . ?
C8 C9 N1 108.41(15) . . ?
C10 C11 N2 129.21(16) . . ?
C10 C11 C12 122.69(16) . . ?
C12 C11 N2 108.09(15) . . ?
O3 C18 C19 117.21(16) . . ?
C17 C18 O3 109.18(15) . . ?
C17 C18 C19 133.58(17) . . ?
C6 C61 H61 121.5 . . ?
C62 C61 H61 121.5 . . ?
C62 C61 C6 116.90(18) . . ?
C131 C13 C12 132.43(18) . . ?
C131 C13 C14 119.90(17) . . ?
C14 C13 C12 107.65(15) . . ?
O2 C5 N1 114.55(16) . . ?
O2 C5 C4 111.04(16) . . ?
C4 C5 N1 134.42(17) . . ?
C81 C12 C11 120.58(16) . . ?
C81 C12 C13 131.89(17) . . ?
C11 C12 C13 107.49(16) . . ?
C13 C131 H131 120.4 . . ?
C132 C131 C13 119.28(18) . . ?
C132 C131 H131 120.4 . . ?
C16 C17 H17 126.0 . . ?
C18 C17 C16 107.91(16) . . ?
C18 C17 H17 126.0 . . ?
C7 C6 N1 108.31(15) . . ?
C61 C6 N1 130.27(17) . . ?
C61 C6 C7 121.43(17) . . ?
C13 C14 N2 108.51(15) . . ?
C141 C14 N2 129.80(17) . . ?
C141 C14 C13 121.66(17) . . ?
C81 C8 C7 132.26(16) . . ?
C81 C8 C9 120.34(16) . . ?
C9 C8 C7 107.40(16) . . ?
C62 C72 H72 119.7 . . ?
C71 C72 H72 119.7 . . ?
C71 C72 C62 120.59(18) . . ?
C14 C141 H141 121.4 . . ?
C142 C141 C14 117.15(18) . . ?
C142 C141 H141 121.4 . . ?
O4 C19 C18 125.12(18) . . ?
O4 C19 H19 117.4 . . ?
C18 C19 H19 117.4 . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
C2 C3 C4 107.94(18) . . ?
C61 C62 C72 122.25(18) . . ?
C61 C62 H62 118.9 . . ?
C72 C62 H62 118.9 . . ?
C5 C4 C3 105.64(18) . . ?
C5 C4 H4 127.2 . . ?
C3 C4 H4 127.2 . . ?
C7 C71 H71 120.8 . . ?
C72 C71 C7 118.43(18) . . ?
C72 C71 H71 120.8 . . ?
C141 C142 H142 118.9 . . ?
C141 C142 C132 122.10(18) . . ?
C132 C142 H142 118.9 . . ?
O2 C2 C1 117.83(19) . . ?
C3 C2 O2 109.14(17) . . ?
C3 C2 C1 133.0(2) . . ?
C131 C132 C142 119.87(18) . . ?
C131 C132 H132 120.1 . . ?
C142 C132 H132 120.1 . . ?
C2 C1 H1 110.3(12) . . ?
O1 C1 C2 126.0(2) . . ?
O1 C1 H1 123.7(12) . . ?

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
O3 C15 C16 C17 -0.50(19) . . . . ?
O3 C18 C17 C16 0.0(2) . . . . ?
O3 C18 C19 O4 2.1(3) . . . . ?
O2 C5 C4 C3 -0.2(2) . . . . ?
O2 C2 C1 O1 -0.6(3) . . . . ?
N1 C9 C8 C81 -179.90(15) . . . . ?
N1 C9 C8 C7 -0.31(19) . . . . ?
N1 C5 C4 C3 179.36(19) . . . . ?
N2 C15 C16 C17 179.00(18) . . . . ?
N2 C11 C12 C81 178.29(15) . . . . ?
N2 C11 C12 C13 0.48(19) . . . . ?
N2 C14 C141 C142 178.33(18) . . . . ?
C15 O3 C18 C17 -0.33(19) . . . . ?
C15 O3 C18 C19 177.85(16) . . . . ?
C15 N2 C11 C10 -3.5(3) . . . . ?
C15 N2 C11 C12 177.48(16) . . . . ?
C15 N2 C14 C13 -176.96(16) . . . . ?
C15 N2 C14 C141 5.1(3) . . . . ?
C15 C16 C17 C18 0.3(2) . . . . ?
C10 C9 C8 C81 -0.1(3) . . . . ?
C10 C9 C8 C7 179.45(16) . . . . ?
C10 C11 C12 C81 -0.8(3) . . . . ?
C10 C11 C12 C13 -178.60(16) . . . . ?
C9 N1 C5 O2 171.60(15) . . . . ?
C9 N1 C5 C4 -8.0(3) . . . . ?
C9 N1 C6 C7 -0.47(18) . . . . ?
C9 N1 C6 C61 179.52(18) . . . . ?
C9 C10 C11 N2 -177.16(16) . . . . ?
C9 C10 C11 C12 1.7(2) . . . . ?
C11 N2 C15 O3 7.1(2) . . . . ?
C11 N2 C15 C16 -172.42(18) . . . . ?
C11 N2 C14 C13 2.14(19) . . . . ?
C11 N2 C14 C141 -175.80(18) . . . . ?
C11 C10 C9 N1 178.46(16) . . . . ?
C11 C10 C9 C8 -1.3(2) . . . . ?
C18 O3 C15 N2 -179.08(14) . . . . ?
C18 O3 C15 C16 0.52(18) . . . . ?
C13 C131 C132 C142 -0.1(3) . . . . ?
C13 C14 C141 C142 0.6(3) . . . . ?
C5 O2 C2 C3 0.6(2) . . . . ?
C5 O2 C2 C1 -178.36(17) . . . . ?
C5 N1 C9 C10 -0.6(3) . . . . ?
C5 N1 C9 C8 179.14(16) . . . . ?
C5 N1 C6 C7 -179.10(16) . . . . ?
C5 N1 C6 C61 0.9(3) . . . . ?
C12 C81 C8 C7 -178.35(17) . . . . ?
C12 C81 C8 C9 1.1(2) . . . . ?
C12 C13 C131 C132 -176.16(19) . . . . ?
C12 C13 C14 N2 -1.82(19) . . . . ?
C12 C13 C14 C141 176.31(16) . . . . ?
C131 C13 C12 C81 1.5(3) . . . . ?
C131 C13 C12 C11 178.95(19) . . . . ?
C131 C13 C14 N2 179.78(16) . . . . ?
C131 C13 C14 C141 -2.1(3) . . . . ?
C17 C18 C19 O4 179.8(2) . . . . ?
C6 N1 C9 C10 -179.26(17) . . . . ?
C6 N1 C9 C8 0.49(18) . . . . ?
C6 N1 C5 O2 -10.0(2) . . . . ?
C6 N1 C5 C4 170.4(2) . . . . ?
C6 C7 C8 C81 179.54(18) . . . . ?
C6 C7 C8 C9 0.02(19) . . . . ?
C6 C7 C71 C72 -0.9(3) . . . . ?
C6 C61 C62 C72 -0.8(3) . . . . ?
C14 N2 C15 O3 -174.01(15) . . . . ?
C14 N2 C15 C16 6.5(3) . . . . ?
C14 N2 C11 C10 177.40(17) . . . . ?
C14 N2 C11 C12 -1.60(18) . . . . ?
C14 C13 C12 C81 -176.63(18) . . . . ?
C14 C13 C12 C11 0.83(19) . . . . ?
C14 C13 C131 C132 1.8(3) . . . . ?
C14 C141 C142 C132 1.1(3) . . . . ?
C8 C81 C12 C11 -0.7(2) . . . . ?
C8 C81 C12 C13 176.52(18) . . . . ?
C8 C7 C6 N1 0.27(19) . . . . ?
C8 C7 C6 C61 -179.71(16) . . . . ?
C8 C7 C71 C72 -179.42(18) . . . . ?
C141 C142 C132 C131 -1.4(3) . . . . ?
C19 C18 C17 C16 -177.74(19) . . . . ?
C3 C2 C1 O1 -179.2(2) . . . . ?
C62 C61 C6 N1 179.44(17) . . . . ?
C62 C61 C6 C7 -0.6(3) . . . . ?
C62 C72 C71 C7 -0.5(3) . . . . ?
C4 C3 C2 O2 -0.8(2) . . . . ?
C4 C3 C2 C1 178.0(2) . . . . ?
C71 C7 C6 N1 -178.59(15) . . . . ?
C71 C7 C6 C61 1.4(3) . . . . ?
C71 C7 C8 C81 -1.8(3) . . . . ?
C71 C7 C8 C9 178.71(18) . . . . ?
C71 C72 C62 C61 1.3(3) . . . . ?
C2 O2 C5 N1 -179.90(15) . . . . ?
C2 O2 C5 C4 -0.2(2) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?

_olex2_date_sample_completion    2023-07-11
_olex2_date_sample_data_collection 2023-07-10
_olex2_date_sample_submission    2023-07-10
_olex2_exptl_crystal_mounting_method 
'mounting on a cryo-loop using paratone oil'
_olex2_submission_original_sample_id MJP_KD_AD00128
_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_mjp_kd_ad00130_mono_2_0ma
_database_code_depnum_ccdc_archive 'CCDC 2373296'
loop_
_audit_author_name
_audit_author_address
'Milosz Pawlicki'
;Faculty of Chemistry, Jagiellonian University
Poland
;
_audit_update_record             
;
2024-07-24 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_audit_creation_date             2024-04-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
''
krzysztof.dzieszkowski@uj.edu.pl
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H16 N2 O2'
_chemical_formula_sum            'C28 H16 N2 O2'
_chemical_formula_weight         412.43
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   23.5151(6)
_cell_length_b                   10.1202(2)
_cell_length_c                   7.7223(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1837.73(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      3.29
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0652 before and 0.0436 after correction.
The Ratio of minimum to maximum transmission is 0.9512.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'slow evaporation from DCM/hexane mixture'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            18575
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_min         3.287
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8Quest Eco Photon50'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           10.0
_diffrn_source_power             0.4
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.914
_reflns_number_gt                2193
_reflns_number_total             2239
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 902 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2239
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.129
_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)+(0.0377P)²+2.4679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0960
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C81(H81), C10(H10), C61(H61), C71(H71), C3(H3), C62(H62), C4(H4), C72(H72),
 C1(H1)
;
_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 0.55998(6) 0.48716(15) 0.4235(2) 0.0135(4) Uani 1 1 d . . . . .
N1 N 0.60342(8) 0.69272(18) 0.3997(3) 0.0124(4) Uani 1 1 d . . . . .
C7 C 0.61022(10) 0.8919(2) 0.5431(3) 0.0115(5) Uani 1 1 d . . . . .
C9 C 0.54909(9) 0.7507(2) 0.4039(3) 0.0120(4) Uani 1 1 d . . . . .
C81 C 0.500000 0.9341(3) 0.5409(5) 0.0119(6) Uani 1 2 d S T P . .
H81 H 0.500001 1.017368 0.597726 0.014 Uiso 1 2 calc R U P . .
C10 C 0.500000 0.6952(3) 0.3402(4) 0.0115(7) Uani 1 2 d S T P . .
H10 H 0.500000 0.624610 0.259078 0.014 Uiso 1 2 calc R U P . .
C61 C 0.69882(10) 0.7660(2) 0.5165(3) 0.0146(5) Uani 1 1 d . . . . .
H61 H 0.719015 0.690091 0.478437 0.018 Uiso 1 1 calc R U . . .
C6 C 0.64100(10) 0.7799(2) 0.4859(3) 0.0130(5) Uani 1 1 d . . . . .
C5 C 0.60918(10) 0.5554(2) 0.3932(3) 0.0131(5) Uani 1 1 d . . . . .
C71 C 0.63848(10) 0.9925(3) 0.6290(3) 0.0143(5) Uani 1 1 d . . . . .
H71 H 0.618461 1.068897 0.666329 0.017 Uiso 1 1 calc R U . . .
C2 C 0.57277(10) 0.3545(2) 0.4105(3) 0.0135(5) Uani 1 1 d . . . . .
C3 C 0.62975(10) 0.3417(2) 0.3815(4) 0.0152(5) Uani 1 1 d . . . . .
H3 H 0.650095 0.260883 0.372149 0.018 Uiso 1 1 calc R U . . .
C62 C 0.72609(10) 0.8675(3) 0.6048(4) 0.0161(5) Uani 1 1 d . . . . .
H62 H 0.765625 0.860197 0.628243 0.019 Uiso 1 1 calc R U . . .
C4 C 0.65326(10) 0.4710(2) 0.3678(4) 0.0157(5) Uani 1 1 d . . . . .
H4 H 0.691792 0.493464 0.345412 0.019 Uiso 1 1 calc R U . . .
C72 C 0.69672(10) 0.9803(3) 0.6600(4) 0.0169(5) Uani 1 1 d . . . . .
H72 H 0.716503 1.048772 0.718842 0.020 Uiso 1 1 calc R U . . .
C8 C 0.55071(10) 0.8707(2) 0.4976(3) 0.0118(5) Uani 1 1 d . . . . .
C1 C 0.52881(10) 0.2557(2) 0.4135(4) 0.0144(5) Uani 1 1 d . . . . .
H1 H 0.543969 0.168675 0.416058 0.017 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 1.367(3) . ?
O1 C2 1.379(3) . ?
N1 C9 1.406(3) . ?
N1 C6 1.415(3) . ?
N1 C5 1.398(3) . ?
C7 C6 1.416(3) . ?
C7 C71 1.385(4) . ?
C7 C8 1.459(3) . ?
C9 C10 1.375(3) . ?
C9 C8 1.414(3) . ?
C81 H81 0.9500 . ?
C81 C8 1.395(3) . ?
C81 C8 1.395(3) 4_655 ?
C10 H10 0.9500 . ?
C61 H61 0.9500 . ?
C61 C6 1.387(3) . ?
C61 C62 1.389(4) . ?
C5 C4 1.357(3) . ?
C71 H71 0.9500 . ?
C71 C72 1.396(3) . ?
C2 C3 1.365(3) . ?
C2 C1 1.439(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.425(3) . ?
C62 H62 0.9500 . ?
C62 C72 1.401(4) . ?
C4 H4 0.9500 . ?
C72 H72 0.9500 . ?
C1 C1 1.355(5) 4_655 ?
C1 H1 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
C5 O1 C2 107.12(17) . . ?
C9 N1 C6 107.24(19) . . ?
C5 N1 C9 120.26(18) . . ?
C5 N1 C6 125.2(2) . . ?
C6 C7 C8 107.3(2) . . ?
C71 C7 C6 119.5(2) . . ?
C71 C7 C8 133.1(2) . . ?
N1 C9 C8 110.2(2) . . ?
C10 C9 N1 125.7(2) . . ?
C10 C9 C8 123.8(2) . . ?
C8 C81 H81 121.2 . . ?
C8 C81 H81 121.2 4_655 . ?
C8 C81 C8 117.5(3) . 4_655 ?
C9 C10 C9 114.2(3) 4_655 . ?
C9 C10 H10 122.9 . . ?
C9 C10 H10 122.9 4_655 . ?
C6 C61 H61 121.3 . . ?
C6 C61 C62 117.5(2) . . ?
C62 C61 H61 121.3 . . ?
N1 C6 C7 109.1(2) . . ?
C61 C6 N1 129.0(2) . . ?
C61 C6 C7 121.9(2) . . ?
O1 C5 N1 114.46(19) . . ?
C4 C5 O1 110.7(2) . . ?
C4 C5 N1 134.8(2) . . ?
C7 C71 H71 120.4 . . ?
C7 C71 C72 119.2(2) . . ?
C72 C71 H71 120.4 . . ?
O1 C2 C1 121.3(2) . . ?
C3 C2 O1 108.6(2) . . ?
C3 C2 C1 129.9(2) . . ?
C2 C3 H3 126.1 . . ?
C2 C3 C4 107.8(2) . . ?
C4 C3 H3 126.1 . . ?
C61 C62 H62 119.2 . . ?
C61 C62 C72 121.6(2) . . ?
C72 C62 H62 119.2 . . ?
C5 C4 C3 105.7(2) . . ?
C5 C4 H4 127.1 . . ?
C3 C4 H4 127.1 . . ?
C71 C72 C62 120.2(2) . . ?
C71 C72 H72 119.9 . . ?
C62 C72 H72 119.9 . . ?
C9 C8 C7 106.0(2) . . ?
C81 C8 C7 134.0(2) . . ?
C81 C8 C9 119.7(2) . . ?
C2 C1 H1 112.0 . . ?
C1 C1 C2 135.93(13) 4_655 . ?
C1 C1 H1 112.0 4_655 . ?

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 C4 C3 0.6(3) . . . . ?
O1 C2 C3 C4 -2.7(3) . . . . ?
O1 C2 C1 C1 6.3(4) . . . 4_655 ?
N1 C9 C10 C9 161.49(18) . . . 4_655 ?
N1 C9 C8 C7 4.1(3) . . . . ?
N1 C9 C8 C81 -170.0(2) . . . . ?
N1 C5 C4 C3 178.6(3) . . . . ?
C7 C71 C72 C62 0.0(4) . . . . ?
C9 N1 C6 C7 -0.2(3) . . . . ?
C9 N1 C6 C61 179.5(3) . . . . ?
C9 N1 C5 O1 -11.4(4) . . . . ?
C9 N1 C5 C4 170.6(3) . . . . ?
C10 C9 C8 C7 178.9(3) . . . . ?
C10 C9 C8 C81 4.8(4) . . . . ?
C61 C62 C72 C71 0.8(4) . . . . ?
C6 N1 C9 C10 -177.2(3) . . . . ?
C6 N1 C9 C8 -2.5(3) . . . . ?
C6 N1 C5 O1 134.8(2) . . . . ?
C6 N1 C5 C4 -43.1(5) . . . . ?
C6 C7 C71 C72 -1.1(4) . . . . ?
C6 C7 C8 C9 -4.1(3) . . . . ?
C6 C7 C8 C81 168.8(3) . . . . ?
C6 C61 C62 C72 -0.5(4) . . . . ?
C5 O1 C2 C3 3.0(3) . . . . ?
C5 O1 C2 C1 -172.0(2) . . . . ?
C5 N1 C9 C10 -25.6(4) . . . . ?
C5 N1 C9 C8 149.1(2) . . . . ?
C5 N1 C6 C7 -150.0(2) . . . . ?
C5 N1 C6 C61 29.7(4) . . . . ?
C71 C7 C6 N1 -178.9(2) . . . . ?
C71 C7 C6 C61 1.4(4) . . . . ?
C71 C7 C8 C9 177.8(3) . . . . ?
C71 C7 C8 C81 -9.3(5) . . . . ?
C2 O1 C5 N1 179.3(2) . . . . ?
C2 O1 C5 C4 -2.2(3) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C2 C1 C1 -167.48(19) . . . 4_655 ?
C62 C61 C6 N1 179.8(3) . . . . ?
C62 C61 C6 C7 -0.6(4) . . . . ?
C8 C7 C6 N1 2.7(3) . . . . ?
C8 C7 C6 C61 -177.0(2) . . . . ?
C8 C7 C71 C72 176.9(3) . . . . ?
C8 C9 C10 C9 -12.6(5) . . . 4_655 ?
C8 C81 C8 C7 -168.32(18) 4_655 . . . ?
C8 C81 C8 C9 3.8(5) 4_655 . . . ?
C1 C2 C3 C4 171.7(3) . . . . ?

_olex2_date_sample_completion    2023-10-13
_olex2_date_sample_data_collection 2023-10-12
_olex2_date_sample_submission    2023-10-12
_olex2_exptl_crystal_mounting_method 
'mounting on a cryo-loop using paratone oil'
_olex2_submission_original_sample_id AD00130
_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_mf008
_database_code_depnum_ccdc_archive 'CCDC 2373297'
loop_
_audit_author_name
_audit_author_address
'Milosz Pawlicki'
;Faculty of Chemistry, Jagiellonian University
Poland
;
_audit_update_record             
;
2024-07-24 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_audit_creation_date             2024-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H20 N2 O4'
_chemical_formula_sum            'C28 H20 N2 O4'
_chemical_formula_weight         448.46
_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                   10.0117(3)
_cell_length_b                   14.9714(4)
_cell_length_c                   15.3960(3)
_cell_angle_alpha                91.5050(18)
_cell_angle_beta                 105.123(2)
_cell_angle_gamma                95.377(2)
_cell_volume                     2214.88(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3832
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      28.5674
_cell_measurement_theta_min      2.9939
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.38
_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  0.0409
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22636
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.813
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean 8.3359
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -74.00   70.75   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -79.0000    0.0000 193

#__ type_ start__ end____ width___ exp.time_
  2 omega  -74.00   -3.50   0.7500   30.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -79.0000   90.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0517221000
_diffrn_orient_matrix_UB_12      -0.0303914000
_diffrn_orient_matrix_UB_13      0.0074291000
_diffrn_orient_matrix_UB_21      -0.0417167000
_diffrn_orient_matrix_UB_22      -0.0295230000
_diffrn_orient_matrix_UB_23      0.0200585000
_diffrn_orient_matrix_UB_31      -0.0323597000
_diffrn_orient_matrix_UB_32      -0.0219586000
_diffrn_orient_matrix_UB_33      -0.0428122000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7973
_reflns_number_total             10060
_reflns_odcompleteness_completeness 59.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.57
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         10060
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0556
_refine_ls_restrained_S_all      1.033
_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)+(0.0853P)²+0.6498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1584
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C235(H235), C21(H21), C71(H71), C1(H1), C27(H27), C8(H8), C241(H241),
 C231(H231), C292(H292), C26(H26), C3(H3), C291(H291), C293(H293), C25(H25),
 C125(H125), C232(H232), C4(H4), C9(H9), C122(H122), C31(H31), C295(H295),
 C14(H14), C234(H234), C15(H15), C121(H121), C20(H20), C18(H18), C10(H10),
 C294(H294), C233(H233), C34(H34), C32(H32), C65(H65), C124(H124), C123(H123),
 C17(H17), C61(H61), C62(H62), C64(H64), C63(H63)
;
_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
O3 O 0.19344(13) 0.52159(8) 0.19884(8) 0.0239(3) Uani 1 1 d . . . . .
O6 O 0.23995(12) 0.11886(8) 0.02818(8) 0.0211(3) Uani 1 1 d . . . . .
O7 O 0.18417(12) 0.02268(7) 0.36061(8) 0.0214(3) Uani 1 1 d . . . . .
O2 O 0.21574(13) 0.65663(8) 0.55219(8) 0.0244(3) Uani 1 1 d . . . . .
O1 O 0.40455(14) 0.67540(9) 0.72465(9) 0.0327(3) Uani 1 1 d . . . . .
O8 O 0.45136(14) 0.11161(9) 0.37195(9) 0.0324(3) Uani 1 1 d . . . . .
O5 O 0.44243(14) 0.08948(10) -0.06416(9) 0.0360(3) Uani 1 1 d . . . . .
N3 N 0.03430(14) 0.13274(9) 0.06915(10) 0.0206(3) Uani 1 1 d . . . . .
N1 N -0.04181(15) 0.47523(9) 0.14556(10) 0.0226(3) Uani 1 1 d . . . . .
O4 O 0.45195(16) 0.61995(10) 0.27847(11) 0.0422(4) Uani 1 1 d . . . . .
N4 N -0.05240(15) -0.01604(9) 0.33202(10) 0.0213(3) Uani 1 1 d . . . . .
N2 N 0.01690(15) 0.64226(10) 0.43381(10) 0.0235(3) Uani 1 1 d . . . . .
C23 C -0.04526(17) 0.13922(11) -0.02174(11) 0.0206(3) Uani 1 1 d . . . . .
C5 C 0.15938(18) 0.65372(11) 0.46193(12) 0.0219(3) Uani 1 1 d . . . . .
C24 C -0.03556(17) 0.12596(10) 0.13958(11) 0.0193(3) Uani 1 1 d . . . . .
C29 C -0.16981(17) -0.07194(10) 0.34432(12) 0.0204(3) Uani 1 1 d . . . . .
C2 C 0.35901(18) 0.67181(11) 0.56580(13) 0.0249(4) Uani 1 1 d . . . . .
C11 C -0.07607(18) 0.54566(10) 0.19807(12) 0.0215(3) Uani 1 1 d . . . . .
C30 C 0.07926(17) -0.03895(10) 0.36710(11) 0.0198(3) Uani 1 1 d . . . . .
C235 C -0.17843(18) 0.09340(11) -0.04924(12) 0.0221(3) Uani 1 1 d . . . . .
H235 H -0.212935 0.057344 -0.008391 0.027 Uiso 1 1 calc R U . . .
C28 C -0.07625(17) 0.05320(10) 0.26864(11) 0.0199(3) Uani 1 1 d . . . . .
C7 C -0.04913(18) 0.62701(11) 0.33903(12) 0.0224(4) Uani 1 1 d . . . . .
C21 C 0.27173(18) 0.14799(11) 0.17742(12) 0.0227(4) Uani 1 1 d . . . . .
H21 H 0.253330 0.160645 0.233719 0.027 Uiso 1 1 calc R U . . .
C71 C -0.01120(18) 0.55878(11) 0.28966(12) 0.0227(4) Uani 1 1 d . . . . .
H71 H 0.057876 0.521879 0.318205 0.027 Uiso 1 1 calc R U . . .
C1 C 0.44425(19) 0.68396(12) 0.65636(13) 0.0271(4) Uani 1 1 d . . . . .
H1 H 0.540854 0.700225 0.664252 0.033 Uiso 1 1 calc R U . . .
C27 C -0.16755(18) 0.11558(11) 0.27782(12) 0.0220(3) Uani 1 1 d . . . . .
H27 H -0.211795 0.112171 0.325404 0.026 Uiso 1 1 calc R U . . .
C22 C 0.17679(17) 0.13487(10) 0.09435(12) 0.0200(3) Uani 1 1 d . . . . .
C8 C -0.15388(18) 0.67909(11) 0.29894(12) 0.0241(4) Uani 1 1 d . . . . .
H8 H -0.179927 0.724700 0.333402 0.029 Uiso 1 1 calc R U . . .
C241 C -0.01236(17) 0.05669(11) 0.19873(11) 0.0201(3) Uani 1 1 d . . . . .
H241 H 0.046427 0.012450 0.191290 0.024 Uiso 1 1 calc R U . . .
C231 C 0.00508(18) 0.19159(11) -0.08240(12) 0.0231(4) Uani 1 1 d . . . . .
H231 H 0.095355 0.223399 -0.064161 0.028 Uiso 1 1 calc R U . . .
C292 C -0.39441(18) -0.15244(11) 0.28007(13) 0.0248(4) Uani 1 1 d . . . . .
H292 H -0.469903 -0.170695 0.229087 0.030 Uiso 1 1 calc R U . . .
C26 C -0.19325(18) 0.18286(11) 0.21665(12) 0.0232(4) Uani 1 1 d . . . . .
H26 H -0.256479 0.224925 0.221870 0.028 Uiso 1 1 calc R U . . .
C19 C 0.38156(17) 0.12184(11) 0.07085(12) 0.0221(3) Uani 1 1 d . . . . .
C3 C 0.38773(19) 0.67565(12) 0.48376(13) 0.0265(4) Uani 1 1 d . . . . .
H3 H 0.477734 0.684486 0.473915 0.032 Uiso 1 1 calc R U . . .
C291 C -0.27933(18) -0.09924(11) 0.26919(12) 0.0224(3) Uani 1 1 d . . . . .
H291 H -0.275347 -0.081618 0.211011 0.027 Uiso 1 1 calc R U . . .
C293 C -0.40025(19) -0.17924(11) 0.36481(13) 0.0271(4) Uani 1 1 d . . . . .
H293 H -0.479004 -0.216158 0.371602 0.033 Uiso 1 1 calc R U . . .
C6 C -0.06861(19) 0.63700(11) 0.49554(12) 0.0242(4) Uani 1 1 d . . . . .
C25 C -0.12655(17) 0.18863(11) 0.14788(12) 0.0215(3) Uani 1 1 d . . . . .
H25 H -0.142997 0.235125 0.106772 0.026 Uiso 1 1 calc R U . . .
C125 C -0.14800(19) 0.39445(11) -0.00101(12) 0.0230(4) Uani 1 1 d . . . . .
H125 H -0.068937 0.414501 -0.021224 0.028 Uiso 1 1 calc R U . . .
C232 C -0.0777(2) 0.19692(12) -0.16975(12) 0.0265(4) Uani 1 1 d . . . . .
H232 H -0.042916 0.231635 -0.211375 0.032 Uiso 1 1 calc R U . . .
C4 C 0.26098(19) 0.66425(11) 0.41659(13) 0.0260(4) Uani 1 1 d . . . . .
H4 H 0.248142 0.663895 0.353228 0.031 Uiso 1 1 calc R U . . .
C9 C -0.22002(19) 0.66367(11) 0.20791(13) 0.0265(4) Uani 1 1 d . . . . .
H9 H -0.293256 0.698039 0.180331 0.032 Uiso 1 1 calc R U . . .
C122 C -0.3808(2) 0.33672(12) 0.05733(14) 0.0293(4) Uani 1 1 d . . . . .
H122 H -0.460621 0.317247 0.077013 0.035 Uiso 1 1 calc R U . . .
C31 C 0.13087(18) -0.11319(11) 0.40995(12) 0.0231(4) Uani 1 1 d . . . . .
H31 H 0.078923 -0.164695 0.423848 0.028 Uiso 1 1 calc R U . . .
C295 C -0.17514(19) -0.09765(11) 0.42992(12) 0.0228(4) Uani 1 1 d . . . . .
H295 H -0.100657 -0.078305 0.481139 0.027 Uiso 1 1 calc R U . . .
C14 C 0.14988(19) 0.38192(11) 0.13297(13) 0.0262(4) Uani 1 1 d . . . . .
H14 H 0.101413 0.327193 0.103633 0.031 Uiso 1 1 calc R U . . .
C234 C -0.26068(19) 0.10037(11) -0.13614(12) 0.0246(4) Uani 1 1 d . . . . .
H234 H -0.351704 0.069606 -0.154326 0.029 Uiso 1 1 calc R U . . .
C15 C 0.2952(2) 0.40443(12) 0.16073(13) 0.0276(4) Uani 1 1 d . . . . .
H15 H 0.363586 0.367239 0.153186 0.033 Uiso 1 1 calc R U . . .
C121 C -0.26998(19) 0.39006(11) 0.11532(13) 0.0248(4) Uani 1 1 d . . . . .
H121 H -0.273693 0.406689 0.174549 0.030 Uiso 1 1 calc R U . . .
C20 C 0.40204(18) 0.13864(11) 0.16116(12) 0.0238(4) Uani 1 1 d . . . . .
H20 H 0.488951 0.143237 0.205370 0.029 Uiso 1 1 calc R U . . .
C33 C 0.30783(18) -0.01433(11) 0.39748(12) 0.0230(4) Uani 1 1 d . . . . .
C18 C 0.47471(19) 0.10510(12) 0.01766(13) 0.0270(4) Uani 1 1 d . . . . .
H18 H 0.570416 0.106151 0.048400 0.032 Uiso 1 1 calc R U . . .
C10 C -0.18003(19) 0.59825(11) 0.15659(12) 0.0245(4) Uani 1 1 d . . . . .
H10 H -0.223255 0.589548 0.093827 0.029 Uiso 1 1 calc R U . . .
C13 C 0.09288(18) 0.45583(11) 0.15724(12) 0.0215(3) Uani 1 1 d . . . . .
C294 C -0.29059(19) -0.15190(11) 0.43959(13) 0.0260(4) Uani 1 1 d . . . . .
H294 H -0.294405 -0.170302 0.497561 0.031 Uiso 1 1 calc R U . . .
C233 C -0.21052(19) 0.15204(12) -0.19652(12) 0.0266(4) Uani 1 1 d . . . . .
H233 H -0.266943 0.156660 -0.255970 0.032 Uiso 1 1 calc R U . . .
C16 C 0.32005(19) 0.48911(12) 0.20037(13) 0.0260(4) Uani 1 1 d . . . . .
C34 C 0.43598(19) 0.03451(12) 0.39536(12) 0.0261(4) Uani 1 1 d . . . . .
H34 H 0.517397 0.004443 0.413864 0.031 Uiso 1 1 calc R U . . .
C32 C 0.27658(19) -0.09661(11) 0.42874(12) 0.0245(4) Uani 1 1 d . . . . .
H32 H 0.341921 -0.135571 0.457975 0.029 Uiso 1 1 calc R U . . .
C65 C -0.1817(2) 0.57185(12) 0.47814(15) 0.0320(4) Uani 1 1 d . . . . .
H65 H -0.201777 0.532523 0.425899 0.038 Uiso 1 1 calc R U . . .
C12 C -0.15407(18) 0.41867(10) 0.08570(12) 0.0214(3) Uani 1 1 d . . . . .
C124 C -0.2590(2) 0.34052(11) -0.05781(13) 0.0279(4) Uani 1 1 d . . . . .
H124 H -0.255103 0.323175 -0.116820 0.033 Uiso 1 1 calc R U . . .
C123 C -0.3750(2) 0.31201(12) -0.02894(14) 0.0305(4) Uani 1 1 d . . . . .
H123 H -0.450544 0.275530 -0.068181 0.037 Uiso 1 1 calc R U . . .
C17 C 0.4452(2) 0.54510(13) 0.24305(14) 0.0320(4) Uani 1 1 d . . . . .
H17 H 0.530712 0.521970 0.243911 0.038 Uiso 1 1 calc R U . . .
C61 C -0.0408(2) 0.69652(14) 0.57055(13) 0.0311(4) Uani 1 1 d . . . . .
H61 H 0.033245 0.743395 0.580559 0.037 Uiso 1 1 calc R U . . .
C62 C -0.1227(2) 0.68645(17) 0.63060(15) 0.0422(5) Uani 1 1 d . . . . .
H62 H -0.102184 0.725208 0.683269 0.051 Uiso 1 1 calc R U . . .
C64 C -0.2652(2) 0.56428(15) 0.53707(17) 0.0416(5) Uani 1 1 d . . . . .
H64 H -0.343846 0.520632 0.524684 0.050 Uiso 1 1 calc R U . . .
C63 C -0.2335(2) 0.62076(17) 0.61445(16) 0.0460(6) Uani 1 1 d . . . . .
H63 H -0.288342 0.614029 0.656218 0.055 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
O3 C13 1.356(2) . ?
O3 C16 1.394(2) . ?
O6 C22 1.359(2) . ?
O6 C19 1.394(2) . ?
O7 C30 1.357(2) . ?
O7 C33 1.393(2) . ?
O2 C5 1.354(2) . ?
O2 C2 1.390(2) . ?
O1 C1 1.223(2) . ?
O8 C34 1.226(2) . ?
O5 C18 1.226(2) . ?
N3 C23 1.429(2) . ?
N3 C24 1.436(2) . ?
N3 C22 1.374(2) . ?
N1 C11 1.432(2) . ?
N1 C13 1.373(2) . ?
N1 C12 1.439(2) . ?
O4 C17 1.222(2) . ?
N4 C29 1.435(2) . ?
N4 C30 1.367(2) . ?
N4 C28 1.436(2) . ?
N2 C5 1.371(2) . ?
N2 C7 1.438(2) . ?
N2 C6 1.435(2) . ?
C23 C235 1.395(2) . ?
C23 C231 1.397(2) . ?
C5 C4 1.376(2) . ?
C24 C241 1.394(2) . ?
C24 C25 1.393(2) . ?
C29 C291 1.392(2) . ?
C29 C295 1.395(2) . ?
C2 C1 1.429(3) . ?
C2 C3 1.368(3) . ?
C11 C71 1.390(2) . ?
C11 C10 1.394(2) . ?
C30 C31 1.381(2) . ?
C235 H235 0.9500 . ?
C235 C234 1.388(2) . ?
C28 C27 1.396(2) . ?
C28 C241 1.388(2) . ?
C7 C71 1.396(2) . ?
C7 C8 1.389(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.377(2) . ?
C21 C20 1.410(2) . ?
C71 H71 0.9500 . ?
C1 H1 0.9500 . ?
C27 H27 0.9500 . ?
C27 C26 1.393(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(3) . ?
C241 H241 0.9500 . ?
C231 H231 0.9500 . ?
C231 C232 1.392(2) . ?
C292 H292 0.9500 . ?
C292 C291 1.388(2) . ?
C292 C293 1.389(3) . ?
C26 H26 0.9500 . ?
C26 C25 1.392(2) . ?
C19 C20 1.364(2) . ?
C19 C18 1.426(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.405(3) . ?
C291 H291 0.9500 . ?
C293 H293 0.9500 . ?
C293 C294 1.389(3) . ?
C6 C65 1.388(3) . ?
C6 C61 1.392(3) . ?
C25 H25 0.9500 . ?
C125 H125 0.9500 . ?
C125 C12 1.392(2) . ?
C125 C124 1.393(3) . ?
C232 H232 0.9500 . ?
C232 C233 1.386(3) . ?
C4 H4 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.394(2) . ?
C122 H122 0.9500 . ?
C122 C121 1.395(3) . ?
C122 C123 1.387(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.408(2) . ?
C295 H295 0.9500 . ?
C295 C294 1.392(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.410(3) . ?
C14 C13 1.377(2) . ?
C234 H234 0.9500 . ?
C234 C233 1.387(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.365(3) . ?
C121 H121 0.9500 . ?
C121 C12 1.390(3) . ?
C20 H20 0.9500 . ?
C33 C34 1.425(3) . ?
C33 C32 1.373(2) . ?
C18 H18 0.9500 . ?
C10 H10 0.9500 . ?
C294 H294 0.9500 . ?
C233 H233 0.9500 . ?
C16 C17 1.432(3) . ?
C34 H34 0.9500 . ?
C32 H32 0.9500 . ?
C65 H65 0.9500 . ?
C65 C64 1.385(3) . ?
C124 H124 0.9500 . ?
C124 C123 1.383(3) . ?
C123 H123 0.9500 . ?
C17 H17 0.9500 . ?
C61 H61 0.9500 . ?
C61 C62 1.389(3) . ?
C62 H62 0.9500 . ?
C62 C63 1.378(4) . ?
C64 H64 0.9500 . ?
C64 C63 1.391(4) . ?
C63 H63 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
C13 O3 C16 106.32(13) . . ?
C22 O6 C19 105.91(13) . . ?
C30 O7 C33 106.64(13) . . ?
C5 O2 C2 106.45(14) . . ?
C23 N3 C24 119.40(13) . . ?
C22 N3 C23 123.54(14) . . ?
C22 N3 C24 117.04(14) . . ?
C11 N1 C12 118.10(14) . . ?
C13 N1 C11 121.70(14) . . ?
C13 N1 C12 119.92(14) . . ?
C29 N4 C28 118.73(13) . . ?
C30 N4 C29 119.99(13) . . ?
C30 N4 C28 120.19(14) . . ?
C5 N2 C7 118.66(14) . . ?
C5 N2 C6 122.59(15) . . ?
C6 N2 C7 118.52(14) . . ?
C235 C23 N3 118.46(15) . . ?
C235 C23 C231 119.56(16) . . ?
C231 C23 N3 121.96(15) . . ?
O2 C5 N2 115.91(15) . . ?
O2 C5 C4 111.16(16) . . ?
N2 C5 C4 132.93(17) . . ?
C241 C24 N3 119.86(14) . . ?
C25 C24 N3 119.58(14) . . ?
C25 C24 C241 120.56(16) . . ?
C291 C29 N4 118.63(15) . . ?
C291 C29 C295 120.54(16) . . ?
C295 C29 N4 120.82(15) . . ?
O2 C2 C1 118.15(16) . . ?
C3 C2 O2 108.74(16) . . ?
C3 C2 C1 133.04(17) . . ?
C71 C11 N1 120.57(15) . . ?
C71 C11 C10 120.55(15) . . ?
C10 C11 N1 118.81(15) . . ?
O7 C30 N4 115.74(14) . . ?
O7 C30 C31 110.96(15) . . ?
N4 C30 C31 133.30(15) . . ?
C23 C235 H235 119.9 . . ?
C234 C235 C23 120.17(16) . . ?
C234 C235 H235 119.9 . . ?
C27 C28 N4 118.44(15) . . ?
C241 C28 N4 120.69(15) . . ?
C241 C28 C27 120.86(15) . . ?
C71 C7 N2 120.07(15) . . ?
C8 C7 N2 118.80(15) . . ?
C8 C7 C71 121.09(16) . . ?
C22 C21 H21 127.3 . . ?
C22 C21 C20 105.35(15) . . ?
C20 C21 H21 127.3 . . ?
C11 C71 C7 118.98(16) . . ?
C11 C71 H71 120.5 . . ?
C7 C71 H71 120.5 . . ?
O1 C1 C2 126.14(17) . . ?
O1 C1 H1 116.9 . . ?
C2 C1 H1 116.9 . . ?
C28 C27 H27 120.3 . . ?
C26 C27 C28 119.45(16) . . ?
C26 C27 H27 120.3 . . ?
O6 C22 N3 117.00(14) . . ?
O6 C22 C21 111.46(14) . . ?
N3 C22 C21 131.51(16) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.19(15) . . ?
C9 C8 H8 120.4 . . ?
C24 C241 H241 120.4 . . ?
C28 C241 C24 119.14(15) . . ?
C28 C241 H241 120.4 . . ?
C23 C231 H231 120.2 . . ?
C232 C231 C23 119.66(16) . . ?
C232 C231 H231 120.2 . . ?
C291 C292 H292 119.7 . . ?
C291 C292 C293 120.61(17) . . ?
C293 C292 H292 119.7 . . ?
C27 C26 H26 119.9 . . ?
C25 C26 C27 120.18(15) . . ?
C25 C26 H26 119.9 . . ?
O6 C19 C18 118.56(15) . . ?
C20 C19 O6 109.20(15) . . ?
C20 C19 C18 132.21(17) . . ?
C2 C3 H3 125.9 . . ?
C2 C3 C4 108.14(17) . . ?
C4 C3 H3 125.9 . . ?
C29 C291 H291 120.3 . . ?
C292 C291 C29 119.36(16) . . ?
C292 C291 H291 120.3 . . ?
C292 C293 H293 120.1 . . ?
C292 C293 C294 119.81(17) . . ?
C294 C293 H293 120.1 . . ?
C65 C6 N2 118.48(16) . . ?
C65 C6 C61 120.41(18) . . ?
C61 C6 N2 121.10(16) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.74(15) . . ?
C26 C25 H25 120.1 . . ?
C12 C125 H125 120.3 . . ?
C12 C125 C124 119.32(17) . . ?
C124 C125 H125 120.3 . . ?
C231 C232 H232 119.7 . . ?
C233 C232 C231 120.60(17) . . ?
C233 C232 H232 119.7 . . ?
C5 C4 C3 105.49(17) . . ?
C5 C4 H4 127.3 . . ?
C3 C4 H4 127.3 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.63(16) . . ?
C10 C9 H9 119.7 . . ?
C121 C122 H122 119.9 . . ?
C123 C122 H122 119.9 . . ?
C123 C122 C121 120.26(18) . . ?
C30 C31 H31 127.2 . . ?
C30 C31 C32 105.60(15) . . ?
C32 C31 H31 127.2 . . ?
C29 C295 H295 120.3 . . ?
C294 C295 C29 119.41(17) . . ?
C294 C295 H295 120.3 . . ?
C15 C14 H14 127.2 . . ?
C13 C14 H14 127.2 . . ?
C13 C14 C15 105.66(16) . . ?
C235 C234 H234 119.9 . . ?
C233 C234 C235 120.29(17) . . ?
C233 C234 H234 119.9 . . ?
C14 C15 H15 126.1 . . ?
C16 C15 C14 107.88(16) . . ?
C16 C15 H15 126.1 . . ?
C122 C121 H121 120.3 . . ?
C12 C121 C122 119.44(17) . . ?
C12 C121 H121 120.3 . . ?
C21 C20 H20 126.0 . . ?
C19 C20 C21 108.08(16) . . ?
C19 C20 H20 126.0 . . ?
O7 C33 C34 118.79(15) . . ?
C32 C33 O7 108.65(15) . . ?
C32 C33 C34 132.55(17) . . ?
O5 C18 C19 125.90(17) . . ?
O5 C18 H18 117.0 . . ?
C19 C18 H18 117.0 . . ?
C11 C10 H10 120.3 . . ?
C9 C10 C11 119.48(16) . . ?
C9 C10 H10 120.3 . . ?
O3 C13 N1 116.05(14) . . ?
O3 C13 C14 111.07(15) . . ?
N1 C13 C14 132.85(16) . . ?
C293 C294 C295 120.26(17) . . ?
C293 C294 H294 119.9 . . ?
C295 C294 H294 119.9 . . ?
C232 C233 C234 119.71(17) . . ?
C232 C233 H233 120.1 . . ?
C234 C233 H233 120.1 . . ?
O3 C16 C17 117.99(16) . . ?
C15 C16 O3 109.07(16) . . ?
C15 C16 C17 132.90(18) . . ?
O8 C34 C33 126.29(17) . . ?
O8 C34 H34 116.9 . . ?
C33 C34 H34 116.9 . . ?
C31 C32 H32 125.9 . . ?
C33 C32 C31 108.11(15) . . ?
C33 C32 H32 125.9 . . ?
C6 C65 H65 120.1 . . ?
C64 C65 C6 119.9(2) . . ?
C64 C65 H65 120.1 . . ?
C125 C12 N1 120.63(16) . . ?
C121 C12 N1 118.83(16) . . ?
C121 C12 C125 120.53(16) . . ?
C125 C124 H124 119.8 . . ?
C123 C124 C125 120.49(18) . . ?
C123 C124 H124 119.8 . . ?
C122 C123 H123 120.0 . . ?
C124 C123 C122 119.96(18) . . ?
C124 C123 H123 120.0 . . ?
O4 C17 C16 125.84(19) . . ?
O4 C17 H17 117.1 . . ?
C16 C17 H17 117.1 . . ?
C6 C61 H61 120.5 . . ?
C62 C61 C6 119.1(2) . . ?
C62 C61 H61 120.5 . . ?
C61 C62 H62 119.7 . . ?
C63 C62 C61 120.6(2) . . ?
C63 C62 H62 119.7 . . ?
C65 C64 H64 120.1 . . ?
C65 C64 C63 119.8(2) . . ?
C63 C64 H64 120.1 . . ?
C62 C63 C64 120.1(2) . . ?
C62 C63 H63 120.0 . . ?
C64 C63 H63 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C16 C17 O4 -0.4(3) . . . . ?
O6 C19 C20 C21 -0.81(19) . . . . ?
O6 C19 C18 O5 1.4(3) . . . . ?
O7 C30 C31 C32 -1.52(19) . . . . ?
O7 C33 C34 O8 7.8(3) . . . . ?
O7 C33 C32 C31 1.2(2) . . . . ?
O2 C5 C4 C3 -0.88(19) . . . . ?
O2 C2 C1 O1 6.1(3) . . . . ?
O2 C2 C3 C4 0.97(19) . . . . ?
N3 C23 C235 C234 177.92(15) . . . . ?
N3 C23 C231 C232 -178.80(15) . . . . ?
N3 C24 C241 C28 177.40(14) . . . . ?
N3 C24 C25 C26 -179.29(15) . . . . ?
N1 C11 C71 C7 -178.80(15) . . . . ?
N1 C11 C10 C9 176.38(16) . . . . ?
N4 C29 C291 C292 -179.24(14) . . . . ?
N4 C29 C295 C294 179.97(15) . . . . ?
N4 C30 C31 C32 179.22(18) . . . . ?
N4 C28 C27 C26 -179.43(15) . . . . ?
N4 C28 C241 C24 -178.65(15) . . . . ?
N2 C5 C4 C3 178.27(17) . . . . ?
N2 C7 C71 C11 -179.70(15) . . . . ?
N2 C7 C8 C9 -178.76(16) . . . . ?
N2 C6 C65 C64 179.16(17) . . . . ?
N2 C6 C61 C62 -177.23(16) . . . . ?
C23 N3 C24 C241 127.63(16) . . . . ?
C23 N3 C24 C25 -52.1(2) . . . . ?
C23 N3 C22 O6 -17.6(2) . . . . ?
C23 N3 C22 C21 164.75(17) . . . . ?
C23 C235 C234 C233 0.7(3) . . . . ?
C23 C231 C232 C233 1.2(3) . . . . ?
C5 O2 C2 C1 175.86(14) . . . . ?
C5 O2 C2 C3 -1.49(18) . . . . ?
C5 N2 C7 C71 52.6(2) . . . . ?
C5 N2 C7 C8 -129.67(17) . . . . ?
C5 N2 C6 C65 -136.44(18) . . . . ?
C5 N2 C6 C61 44.6(2) . . . . ?
C24 N3 C23 C235 -34.0(2) . . . . ?
C24 N3 C23 C231 144.35(16) . . . . ?
C24 N3 C22 O6 164.10(13) . . . . ?
C24 N3 C22 C21 -13.6(3) . . . . ?
C29 N4 C30 O7 -173.12(14) . . . . ?
C29 N4 C30 C31 6.1(3) . . . . ?
C29 N4 C28 C27 54.5(2) . . . . ?
C29 N4 C28 C241 -124.06(17) . . . . ?
C29 C295 C294 C293 -0.8(2) . . . . ?
C2 O2 C5 N2 -177.84(14) . . . . ?
C2 O2 C5 C4 1.48(18) . . . . ?
C2 C3 C4 C5 -0.08(19) . . . . ?
C11 N1 C13 O3 -19.7(2) . . . . ?
C11 N1 C13 C14 162.19(19) . . . . ?
C11 N1 C12 C125 137.14(16) . . . . ?
C11 N1 C12 C121 -41.6(2) . . . . ?
C30 O7 C33 C34 176.82(15) . . . . ?
C30 O7 C33 C32 -2.09(18) . . . . ?
C30 N4 C29 C291 -129.04(17) . . . . ?
C30 N4 C29 C295 51.7(2) . . . . ?
C30 N4 C28 C27 -137.43(17) . . . . ?
C30 N4 C28 C241 44.0(2) . . . . ?
C30 C31 C32 C33 0.2(2) . . . . ?
C235 C23 C231 C232 -0.5(3) . . . . ?
C235 C234 C233 C232 -0.1(3) . . . . ?
C28 N4 C29 C291 39.0(2) . . . . ?
C28 N4 C29 C295 -140.21(16) . . . . ?
C28 N4 C30 O7 19.0(2) . . . . ?
C28 N4 C30 C31 -161.80(18) . . . . ?
C28 C27 C26 C25 -1.1(3) . . . . ?
C7 N2 C5 O2 -172.10(13) . . . . ?
C7 N2 C5 C4 8.8(3) . . . . ?
C7 N2 C6 C65 37.9(2) . . . . ?
C7 N2 C6 C61 -141.06(17) . . . . ?
C7 C8 C9 C10 -1.5(3) . . . . ?
C71 C11 C10 C9 -0.8(3) . . . . ?
C71 C7 C8 C9 -1.0(3) . . . . ?
C1 C2 C3 C4 -175.84(18) . . . . ?
C27 C28 C241 C24 2.8(2) . . . . ?
C27 C26 C25 C24 1.0(3) . . . . ?
C22 O6 C19 C20 0.49(17) . . . . ?
C22 O6 C19 C18 178.55(15) . . . . ?
C22 N3 C23 C235 147.72(16) . . . . ?
C22 N3 C23 C231 -33.9(2) . . . . ?
C22 N3 C24 C241 -54.0(2) . . . . ?
C22 N3 C24 C25 126.30(17) . . . . ?
C22 C21 C20 C19 0.79(19) . . . . ?
C8 C7 C71 C11 2.6(3) . . . . ?
C8 C9 C10 C11 2.4(3) . . . . ?
C241 C24 C25 C26 1.0(3) . . . . ?
C241 C28 C27 C26 -0.9(3) . . . . ?
C231 C23 C235 C234 -0.5(2) . . . . ?
C231 C232 C233 C234 -0.9(3) . . . . ?
C292 C293 C294 C295 0.1(3) . . . . ?
C19 O6 C22 N3 -178.12(13) . . . . ?
C19 O6 C22 C21 0.02(17) . . . . ?
C3 C2 C1 O1 -177.28(19) . . . . ?
C291 C29 C295 C294 0.7(2) . . . . ?
C291 C292 C293 C294 0.6(3) . . . . ?
C293 C292 C291 C29 -0.7(2) . . . . ?
C6 N2 C5 O2 2.3(2) . . . . ?
C6 N2 C5 C4 -176.84(17) . . . . ?
C6 N2 C7 C71 -122.02(17) . . . . ?
C6 N2 C7 C8 55.7(2) . . . . ?
C6 C65 C64 C63 -1.4(3) . . . . ?
C6 C61 C62 C63 -2.6(3) . . . . ?
C25 C24 C241 C28 -2.9(2) . . . . ?
C125 C124 C123 C122 -0.4(3) . . . . ?
C122 C121 C12 N1 178.69(15) . . . . ?
C122 C121 C12 C125 -0.1(2) . . . . ?
C295 C29 C291 C292 0.0(2) . . . . ?
C14 C15 C16 O3 0.1(2) . . . . ?
C14 C15 C16 C17 177.7(2) . . . . ?
C15 C14 C13 O3 -0.7(2) . . . . ?
C15 C14 C13 N1 177.53(19) . . . . ?
C15 C16 C17 O4 -177.8(2) . . . . ?
C121 C122 C123 C124 -0.2(3) . . . . ?
C20 C21 C22 O6 -0.50(18) . . . . ?
C20 C21 C22 N3 177.29(17) . . . . ?
C20 C19 C18 O5 178.91(19) . . . . ?
C33 O7 C30 N4 -178.35(14) . . . . ?
C33 O7 C30 C31 2.24(18) . . . . ?
C18 C19 C20 C21 -178.50(18) . . . . ?
C10 C11 C71 C7 -1.7(3) . . . . ?
C13 O3 C16 C15 -0.5(2) . . . . ?
C13 O3 C16 C17 -178.52(16) . . . . ?
C13 N1 C11 C71 -40.8(2) . . . . ?
C13 N1 C11 C10 142.04(17) . . . . ?
C13 N1 C12 C125 -48.8(2) . . . . ?
C13 N1 C12 C121 132.44(17) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C16 O3 C13 N1 -177.79(15) . . . . ?
C16 O3 C13 C14 0.7(2) . . . . ?
C34 C33 C32 C31 -177.51(18) . . . . ?
C32 C33 C34 O8 -173.58(19) . . . . ?
C65 C6 C61 C62 3.8(3) . . . . ?
C65 C64 C63 C62 2.6(3) . . . . ?
C12 N1 C11 C71 133.14(17) . . . . ?
C12 N1 C11 C10 -44.0(2) . . . . ?
C12 N1 C13 O3 166.51(14) . . . . ?
C12 N1 C13 C14 -11.6(3) . . . . ?
C12 C125 C124 C123 0.7(3) . . . . ?
C124 C125 C12 N1 -179.22(15) . . . . ?
C124 C125 C12 C121 -0.5(2) . . . . ?
C123 C122 C121 C12 0.4(3) . . . . ?
C61 C6 C65 C64 -1.8(3) . . . . ?
C61 C62 C63 C64 -0.6(3) . . . . ?

_olex2_date_sample_data_collection 2019-10-22
_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_mjp_mf9
_database_code_depnum_ccdc_archive 'CCDC 2373299'
loop_
_audit_author_name
_audit_author_address
'Milosz Pawlicki'
;Faculty of Chemistry, Jagiellonian University
Poland
;
_audit_update_record             
;
2024-07-24 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_audit_creation_date             2024-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H20 N2 O2'
_chemical_formula_sum            'C28 H20 N2 O2'
_chemical_formula_weight         416.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

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

_cell_length_a                   8.20060(10)
_cell_length_b                   25.6429(3)
_cell_length_c                   9.61100(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.6740(10)
_cell_angle_gamma                90
_cell_volume                     2014.35(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6477
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      77.8403
_cell_measurement_theta_min      1.7228
_shelx_estimated_absorpt_T_max   0.861
_shelx_estimated_absorpt_T_min   0.715
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.5192
_exptl_crystal_size_mid          0.2677
_exptl_crystal_size_min          0.2238
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9406
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.841
_diffrn_reflns_theta_min         3.447
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean 8.1956
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -106.00  -53.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6143  -37.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
  2 omega -100.00   -9.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6143  -77.0000  120.0000 91

#__ type_ start__ end____ width___ exp.time_
  3 omega    0.00   85.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6143 -125.0000  -30.0000 85

#__ type_ start__ end____ width___ exp.time_
  4 omega   40.00   71.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
  5 omega   41.00   77.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega   51.00   76.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   41.00   77.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
  8 omega   95.00  121.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  135.00  161.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00  115.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -46.0000 78

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00   85.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
 12 omega  101.00  134.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 13 omega   90.00  116.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   90.00  124.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
 15 omega  145.00  177.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
 16 omega   86.00  173.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 87

#__ type_ start__ end____ width___ exp.time_
 17 omega   73.00  102.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -107.0000  162.0000 29
;
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0206796000
_diffrn_orient_matrix_UB_12      -0.0588319000
_diffrn_orient_matrix_UB_13      -0.0288761000
_diffrn_orient_matrix_UB_21      0.1654813000
_diffrn_orient_matrix_UB_22      -0.0008598000
_diffrn_orient_matrix_UB_23      -0.0653551000
_diffrn_orient_matrix_UB_31      0.0879765000
_diffrn_orient_matrix_UB_32      -0.0121273000
_diffrn_orient_matrix_UB_33      0.1440198000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3836
_reflns_number_total             4210
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         4210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0654
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1315P)²+0.3445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1723
_refine_ls_wR_factor_ref         0.1800
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 -0.66318(13) 0.13015(4) 2.38341(11) 0.0220(3) Uani 1 1 d . . . . .
O2 O -0.94587(14) 0.06947(4) 2.33306(11) 0.0248(3) Uani 1 1 d . . . . .
N1 N -0.64370(15) 0.20627(5) 2.25130(13) 0.0221(3) Uani 1 1 d . . . . .
N2 N -1.13188(17) 0.10288(5) 2.15720(14) 0.0283(3) Uani 1 1 d . . . . .
C7 C -0.56001(17) 0.25363(5) 2.22293(15) 0.0215(3) Uani 1 1 d . . . . .
C12 C -1.05956(18) 0.15292(6) 2.16473(14) 0.0222(3) Uani 1 1 d . . . . .
C17 C -0.87125(19) 0.02261(6) 2.37072(16) 0.0245(3) Uani 1 1 d . . . . .
C3 C -0.56792(18) 0.10109(6) 2.48146(14) 0.0228(3) Uani 1 1 d . . . . .
C14 C -1.04577(19) 0.06026(6) 2.21448(16) 0.0252(3) Uani 1 1 d . . . . .
C4 C -0.42027(19) 0.12515(6) 2.50521(15) 0.0249(3) Uani 1 1 d . . . . .
C6 C -0.57043(18) 0.17161(5) 2.34829(14) 0.0207(3) Uani 1 1 d . . . . .
C75 C -0.54930(19) 0.26767(6) 2.08414(16) 0.0243(3) Uani 1 1 d . . . . .
C8 C -0.81531(18) 0.20439(5) 2.21288(14) 0.0205(3) Uani 1 1 d . . . . .
C72 C -0.4275(2) 0.33407(6) 2.29675(17) 0.0267(3) Uani 1 1 d . . . . .
C81 C -0.88875(18) 0.15701(5) 2.17743(14) 0.0210(3) Uani 1 1 d . . . . .
C2 C -0.62549(19) 0.05248(6) 2.53199(15) 0.0247(3) Uani 1 1 d . . . . .
C11 C -1.15519(19) 0.19786(6) 2.16723(15) 0.0244(3) Uani 1 1 d . . . . .
C9 C -0.90972(19) 0.24978(5) 2.21681(15) 0.0229(3) Uani 1 1 d . . . . .
C71 C -0.49721(19) 0.28641(6) 2.32982(16) 0.0248(3) Uani 1 1 d . . . . .
C5 C -0.41957(19) 0.17004(6) 2.41921(15) 0.0246(3) Uani 1 1 d . . . . .
C13 C -1.28998(19) 0.09438(6) 2.08842(16) 0.0249(3) Uani 1 1 d . . . . .
C10 C -1.07902(19) 0.24592(6) 2.18980(15) 0.0235(3) Uani 1 1 d . . . . .
C74 C -0.47996(19) 0.31512(6) 2.05198(16) 0.0257(3) Uani 1 1 d . . . . .
C15 C -1.0413(2) 0.00943(6) 2.17775(17) 0.0293(4) Uani 1 1 d . . . . .
C1 C -0.7489(2) 0.01974(6) 2.48710(17) 0.0271(3) Uani 1 1 d . . . . .
C73 C -0.41888(19) 0.34852(6) 2.15844(17) 0.0269(3) Uani 1 1 d . . . . .
C16 C -0.9308(2) -0.01508(6) 2.28071(19) 0.0301(4) Uani 1 1 d . . . . .
C131 C -1.3290(2) 0.11556(7) 1.95613(17) 0.0296(4) Uani 1 1 d . . . . .
C135 C -1.4063(2) 0.06508(6) 2.15233(17) 0.0271(3) Uani 1 1 d . . . . .
C134 C -1.5594(2) 0.05640(6) 2.08391(19) 0.0310(4) Uani 1 1 d . . . . .
C132 C -1.4839(2) 0.10765(7) 1.88953(17) 0.0321(4) Uani 1 1 d . . . . .
C133 C -1.5987(2) 0.07748(6) 1.9522(2) 0.0326(4) Uani 1 1 d . . . . .
H9 H -0.859(3) 0.2838(8) 2.237(2) 0.024(5) Uiso 1 1 d . . . . .
H1 H -0.748(3) -0.0136(8) 2.532(2) 0.027(5) Uiso 1 1 d . . . . .
H74 H -0.473(3) 0.3234(8) 1.958(2) 0.025(5) Uiso 1 1 d . . . . .
H73 H -0.382(3) 0.3829(8) 2.134(2) 0.025(5) Uiso 1 1 d . . . . .
H2 H -0.549(3) 0.0399(8) 2.613(2) 0.029(5) Uiso 1 1 d . . . . .
H71 H -0.505(2) 0.2757(7) 2.422(2) 0.022(4) Uiso 1 1 d . . . . .
H75 H -0.590(3) 0.2451(8) 2.014(2) 0.025(5) Uiso 1 1 d . . . . .
H10 H -1.142(3) 0.2774(9) 2.189(2) 0.031(5) Uiso 1 1 d . . . . .
H81 H -0.821(3) 0.1247(8) 2.1696(19) 0.024(4) Uiso 1 1 d . . . . .
H16 H -0.903(3) -0.0513(9) 2.288(2) 0.037(6) Uiso 1 1 d . . . . .
H15 H -1.097(3) -0.0056(10) 2.090(3) 0.044(6) Uiso 1 1 d . . . . .
H132 H -1.508(3) 0.1224(8) 1.801(2) 0.033(5) Uiso 1 1 d . . . . .
H72 H -0.382(3) 0.3573(10) 2.364(3) 0.044(6) Uiso 1 1 d . . . . .
H4 H -0.330(3) 0.1144(8) 2.570(2) 0.032(5) Uiso 1 1 d . . . . .
H134 H -1.627(3) 0.0362(9) 2.134(2) 0.034(5) Uiso 1 1 d . . . . .
H133 H -1.711(3) 0.0700(9) 1.905(2) 0.041(6) Uiso 1 1 d . . . . .
H135 H -1.375(3) 0.0511(8) 2.245(2) 0.033(5) Uiso 1 1 d . . . . .
H131 H -1.254(3) 0.1363(9) 1.911(2) 0.034(5) Uiso 1 1 d . . . . .
H11 H -1.281(3) 0.1936(9) 2.147(2) 0.036(6) Uiso 1 1 d . . . . .
H5 H -0.330(3) 0.1967(9) 2.417(2) 0.033(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3906(17) . ?
O1 C6 1.3656(17) . ?
O2 C17 1.3832(17) . ?
O2 C14 1.3689(18) . ?
N1 C7 1.4320(18) . ?
N1 C6 1.3887(18) . ?
N1 C8 1.4263(18) . ?
N2 C12 1.4132(19) . ?
N2 C14 1.390(2) . ?
N2 C13 1.423(2) . ?
C7 C75 1.391(2) . ?
C7 C71 1.393(2) . ?
C12 C81 1.400(2) . ?
C12 C11 1.395(2) . ?
C17 C1 1.442(2) . ?
C17 C16 1.361(2) . ?
C3 C4 1.362(2) . ?
C3 C2 1.432(2) . ?
C14 C15 1.352(2) . ?
C4 C5 1.418(2) . ?
C4 H4 0.97(2) . ?
C6 C5 1.364(2) . ?
C75 C74 1.389(2) . ?
C75 H75 0.93(2) . ?
C8 C81 1.386(2) . ?
C8 C9 1.400(2) . ?
C72 C71 1.397(2) . ?
C72 C73 1.387(2) . ?
C72 H72 0.94(3) . ?
C81 H81 1.00(2) . ?
C2 C1 1.358(2) . ?
C2 H2 1.01(2) . ?
C11 C10 1.391(2) . ?
C11 H11 1.04(2) . ?
C9 C10 1.395(2) . ?
C9 H9 0.98(2) . ?
C71 H71 0.94(2) . ?
C5 H5 1.00(2) . ?
C13 C131 1.396(2) . ?
C13 C135 1.395(2) . ?
C10 H10 0.96(2) . ?
C74 C73 1.396(2) . ?
C74 H74 0.93(2) . ?
C15 C16 1.432(2) . ?
C15 H15 1.00(3) . ?
C1 H1 0.96(2) . ?
C73 H73 0.97(2) . ?
C16 H16 0.96(2) . ?
C131 C132 1.390(2) . ?
C131 H131 0.95(2) . ?
C135 C134 1.387(2) . ?
C135 H135 0.98(2) . ?
C134 C133 1.390(3) . ?
C134 H134 0.92(2) . ?
C132 C133 1.392(3) . ?
C132 H132 0.94(2) . ?
C133 H133 1.01(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
C6 O1 C3 106.94(11) . . ?
C14 O2 C17 106.85(12) . . ?
C6 N1 C7 118.85(12) . . ?
C6 N1 C8 121.06(12) . . ?
C8 N1 C7 117.22(11) . . ?
C12 N2 C13 121.70(13) . . ?
C14 N2 C12 119.74(13) . . ?
C14 N2 C13 118.53(13) . . ?
C75 C7 N1 118.08(13) . . ?
C75 C7 C71 120.15(14) . . ?
C71 C7 N1 121.70(13) . . ?
C81 C12 N2 119.02(13) . . ?
C11 C12 N2 121.12(14) . . ?
C11 C12 C81 119.77(13) . . ?
O2 C17 C1 120.82(13) . . ?
C16 C17 O2 108.82(14) . . ?
C16 C17 C1 130.35(14) . . ?
O1 C3 C2 120.92(13) . . ?
C4 C3 O1 108.27(13) . . ?
C4 C3 C2 130.62(14) . . ?
O2 C14 N2 116.37(13) . . ?
C15 C14 O2 110.91(14) . . ?
C15 C14 N2 132.71(15) . . ?
C3 C4 C5 108.43(13) . . ?
C3 C4 H4 127.1(13) . . ?
C5 C4 H4 124.5(13) . . ?
O1 C6 N1 116.42(12) . . ?
C5 C6 O1 110.75(12) . . ?
C5 C6 N1 132.83(14) . . ?
C7 C75 H75 119.0(13) . . ?
C74 C75 C7 119.95(14) . . ?
C74 C75 H75 121.1(13) . . ?
C81 C8 N1 119.54(12) . . ?
C81 C8 C9 120.34(14) . . ?
C9 C8 N1 120.07(13) . . ?
C71 C72 H72 123.0(15) . . ?
C73 C72 C71 120.36(14) . . ?
C73 C72 H72 116.6(16) . . ?
C12 C81 H81 119.1(12) . . ?
C8 C81 C12 119.91(13) . . ?
C8 C81 H81 120.8(12) . . ?
C3 C2 H2 109.8(13) . . ?
C1 C2 C3 133.49(14) . . ?
C1 C2 H2 116.4(13) . . ?
C12 C11 H11 117.5(13) . . ?
C10 C11 C12 119.25(14) . . ?
C10 C11 H11 123.2(12) . . ?
C8 C9 H9 121.2(12) . . ?
C10 C9 C8 118.70(13) . . ?
C10 C9 H9 120.1(12) . . ?
C7 C71 C72 119.59(14) . . ?
C7 C71 H71 118.2(12) . . ?
C72 C71 H71 122.2(12) . . ?
C4 C5 H5 127.2(13) . . ?
C6 C5 C4 105.60(13) . . ?
C6 C5 H5 127.0(13) . . ?
C131 C13 N2 119.74(14) . . ?
C135 C13 N2 120.50(14) . . ?
C135 C13 C131 119.76(15) . . ?
C11 C10 C9 121.29(13) . . ?
C11 C10 H10 120.5(14) . . ?
C9 C10 H10 118.2(14) . . ?
C75 C74 C73 120.23(14) . . ?
C75 C74 H74 118.2(12) . . ?
C73 C74 H74 121.6(13) . . ?
C14 C15 C16 105.77(14) . . ?
C14 C15 H15 124.8(15) . . ?
C16 C15 H15 129.2(15) . . ?
C17 C1 H1 112.0(13) . . ?
C2 C1 C17 131.93(14) . . ?
C2 C1 H1 115.5(13) . . ?
C72 C73 C74 119.69(14) . . ?
C72 C73 H73 121.4(11) . . ?
C74 C73 H73 118.6(11) . . ?
C17 C16 C15 107.55(14) . . ?
C17 C16 H16 125.0(14) . . ?
C15 C16 H16 127.4(14) . . ?
C13 C131 H131 122.0(14) . . ?
C132 C131 C13 119.73(16) . . ?
C132 C131 H131 118.3(14) . . ?
C13 C135 H135 117.4(13) . . ?
C134 C135 C13 120.16(15) . . ?
C134 C135 H135 122.4(13) . . ?
C135 C134 C133 120.20(16) . . ?
C135 C134 H134 113.9(14) . . ?
C133 C134 H134 125.9(14) . . ?
C131 C132 C133 120.43(16) . . ?
C131 C132 H132 118.5(14) . . ?
C133 C132 H132 121.1(14) . . ?
C134 C133 C132 119.68(16) . . ?
C134 C133 H133 118.2(14) . . ?
C132 C133 H133 122.1(14) . . ?

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 C3 C4 C5 -0.95(17) . . . . ?
O1 C3 C2 C1 15.2(3) . . . . ?
O1 C6 C5 C4 -0.94(17) . . . . ?
O2 C17 C1 C2 -39.4(3) . . . . ?
O2 C17 C16 C15 3.01(18) . . . . ?
O2 C14 C15 C16 0.05(19) . . . . ?
N1 C7 C75 C74 175.24(13) . . . . ?
N1 C7 C71 C72 -175.20(14) . . . . ?
N1 C6 C5 C4 178.92(15) . . . . ?
N1 C8 C81 C12 168.23(12) . . . . ?
N1 C8 C9 C10 -174.79(12) . . . . ?
N2 C12 C81 C8 -167.08(13) . . . . ?
N2 C12 C11 C10 173.12(13) . . . . ?
N2 C14 C15 C16 -178.79(17) . . . . ?
N2 C13 C131 C132 -179.42(15) . . . . ?
N2 C13 C135 C134 -179.17(14) . . . . ?
C7 N1 C6 O1 172.62(12) . . . . ?
C7 N1 C6 C5 -7.2(2) . . . . ?
C7 N1 C8 C81 150.95(13) . . . . ?
C7 N1 C8 C9 -31.75(19) . . . . ?
C7 C75 C74 C73 0.9(2) . . . . ?
C12 N2 C14 O2 34.6(2) . . . . ?
C12 N2 C14 C15 -146.58(18) . . . . ?
C12 N2 C13 C131 47.0(2) . . . . ?
C12 N2 C13 C135 -132.88(16) . . . . ?
C12 C11 C10 C9 -3.2(2) . . . . ?
C17 O2 C14 N2 -179.18(13) . . . . ?
C17 O2 C14 C15 1.77(18) . . . . ?
C3 O1 C6 N1 -179.50(12) . . . . ?
C3 O1 C6 C5 0.38(16) . . . . ?
C3 C4 C5 C6 1.15(17) . . . . ?
C3 C2 C1 C17 -1.2(3) . . . . ?
C14 O2 C17 C1 175.73(14) . . . . ?
C14 O2 C17 C16 -2.97(17) . . . . ?
C14 N2 C12 C81 24.9(2) . . . . ?
C14 N2 C12 C11 -151.64(15) . . . . ?
C14 N2 C13 C131 -131.07(16) . . . . ?
C14 N2 C13 C135 49.0(2) . . . . ?
C14 C15 C16 C17 -1.89(19) . . . . ?
C4 C3 C2 C1 -159.23(18) . . . . ?
C6 O1 C3 C4 0.37(16) . . . . ?
C6 O1 C3 C2 -175.15(13) . . . . ?
C6 N1 C7 C75 132.73(14) . . . . ?
C6 N1 C7 C71 -50.3(2) . . . . ?
C6 N1 C8 C81 -48.41(19) . . . . ?
C6 N1 C8 C9 128.88(14) . . . . ?
C75 C7 C71 C72 1.7(2) . . . . ?
C75 C74 C73 C72 0.1(2) . . . . ?
C8 N1 C7 C75 -66.19(18) . . . . ?
C8 N1 C7 C71 110.79(16) . . . . ?
C8 N1 C6 O1 12.29(19) . . . . ?
C8 N1 C6 C5 -167.56(15) . . . . ?
C8 C9 C10 C11 3.7(2) . . . . ?
C81 C12 C11 C10 -3.4(2) . . . . ?
C81 C8 C9 C10 2.5(2) . . . . ?
C2 C3 C4 C5 173.99(15) . . . . ?
C11 C12 C81 C8 9.5(2) . . . . ?
C9 C8 C81 C12 -9.1(2) . . . . ?
C71 C7 C75 C74 -1.8(2) . . . . ?
C71 C72 C73 C74 -0.2(2) . . . . ?
C13 N2 C12 C81 -153.21(14) . . . . ?
C13 N2 C12 C11 30.3(2) . . . . ?
C13 N2 C14 O2 -147.21(14) . . . . ?
C13 N2 C14 C15 31.6(3) . . . . ?
C13 C131 C132 C133 -1.9(3) . . . . ?
C13 C135 C134 C133 -1.0(2) . . . . ?
C1 C17 C16 C15 -175.52(16) . . . . ?
C73 C72 C71 C7 -0.7(2) . . . . ?
C16 C17 C1 C2 139.0(2) . . . . ?
C131 C13 C135 C134 0.9(2) . . . . ?
C131 C132 C133 C134 1.8(3) . . . . ?
C135 C13 C131 C132 0.5(2) . . . . ?
C135 C134 C133 C132 -0.4(3) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4 -5 4 0.0944 3.7665 -4.6299 3.6839 0.0881 0.3865 0.9181
-5 5 1 0.1077 -5.0680 5.0746 0.5781 -0.2104 -0.8808 -0.4242
5 -5 2 0.0920 4.5272 -5.1059 2.2282 0.1424 0.6079 0.7811
-1 -16 1 0.0860 -1.2167 -16.1406 0.6498 0.9560 -0.2299 0.1823
2 -2 5 0.1681 2.2526 -2.1637 5.3641 -0.0742 0.0240 0.9970
-2 2 -5 0.1534 -2.2931 1.7097 -5.3596 0.1016 -0.0307 -0.9944
-2 -16 0 0.0863 -1.6552 -15.7482 -0.3885 0.9719 -0.2350 -0.0106
0 1 -6 0.1760 0.0131 1.4679 -6.1976 0.0923 0.4059 -0.9092
-5 5 -1 0.1223 -4.8459 5.3461 -1.1616 -0.1808 -0.7306 -0.6585
2 -3 5 0.1660 2.0627 -3.4988 5.3885 0.0076 -0.0078 0.9999
-2 0 -5 0.1583 -2.3758 -0.0570 -5.3401 0.2067 -0.0441 -0.9774
2 15 1 0.1117 2.0193 14.7804 1.4156 -0.9522 0.2289 0.2023

_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_ad00130_dimer_auto
_database_code_depnum_ccdc_archive 'CCDC 2373301'
loop_
_audit_author_name
_audit_author_address
'Milosz Pawlicki'
;Faculty of Chemistry, Jagiellonian University
Poland
;
_audit_update_record             
;
2024-07-24 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_audit_creation_date             2024-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C56 H32 N4 O4'
_chemical_formula_sum            'C56 H32 N4 O4'
_chemical_formula_weight         824.85
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.55069(18)
_cell_length_b                   28.1034(4)
_cell_length_c                   12.47602(19)
_cell_angle_alpha                90
_cell_angle_beta                 107.3208(17)
_cell_angle_gamma                90
_cell_volume                     3866.23(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12786
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.2340
_cell_measurement_theta_min      3.1550
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            52809
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.667
_diffrn_reflns_theta_min         3.145
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00  71.00   0.50    8.00    --   62.47-107.00 120.00   80
  2  ω    -63.00 -32.00   0.50    8.00    --  -63.45 107.00-141.00   62
  3  ω    -87.00 -62.00   0.50    8.00    --  -74.78 107.00-141.00   50
  4  ω     40.00  65.00   0.50    8.00    --   75.82-107.00 120.00   50
  5  ω     41.00  66.00   0.50    8.00    --   76.76-107.00 120.00   50
  6  ω    -92.00 -65.00   0.50    8.00    --  -76.84 107.00-141.00   54
  7  ω     25.00  71.00   0.50    8.00    --   62.47 -95.00-180.00   92
  8  ω     43.00  77.00   0.50    8.00    --   62.47   0.00 -90.00   68
  9  ω     30.00  56.00   0.50    8.00    --   62.47 -95.00  60.00   52
 10  ω     26.00  63.00   0.50    8.00    --   62.47 -95.00 -30.00   74
 11  ω    -84.00 -28.00   0.50    8.00    --  -63.45   0.00 -30.00  112
 12  ω   -112.00 -38.00   0.50    8.00    --  -74.78   0.00-120.00  148
 13  ω    -97.00 -68.00   0.50    8.00    --  -74.78 126.00 150.00   58
 14  ω    -62.00 -37.00   0.50    8.00    --  -74.78 126.00 150.00   50
 15  ω   -119.00 -94.00   0.50    8.00    --  -76.84-126.00 120.00   50
 16  ω   -112.00 -87.00   0.50    8.00    --  -76.84-126.00  60.00   50
 17  ω   -107.00 -61.00   0.50    8.00    --  -79.25 130.00 141.81   92
 18  ω    -71.00 -46.00   0.50    8.00    --  -79.25  66.00-147.42   50
 19  ω    -70.00 -42.00   0.50    8.00    --  -79.25 100.00-168.84   56
 20  ω    -68.00 -40.00   0.50    8.00    --  -79.25  64.00 149.82   56
 21  ω    -67.00 -41.00   0.50    8.00    --  -79.25 121.00 139.29   52
 22  ω    -61.00 -36.00   0.50    8.00    --  -79.25  56.00-162.85   50
 23  ω    -83.00 -47.00   0.50    8.00    --  -79.25 124.00 104.53   72
 24  ω    -95.00 -69.00   0.50    8.00    --  -79.25 121.00 139.29   52
 25  ω   -119.00 -93.00   0.50    8.00    --  -79.25 144.00  62.85   52
 26  ω    -94.00 -40.00   0.50    8.00    --  -79.25 111.00-126.09  108
 27  ω   -124.00 -98.00   0.50    8.00    --  -79.25 -42.00 146.35   52
 28  ω   -114.00 -89.00   0.50    8.00    --  -79.25 -77.00  64.74   50
 29  ω   -114.00 -88.00   0.50    8.00    --  -79.25 136.00 133.99   52
 30  ω   -105.00 -64.00   0.50    8.00    --  -79.25 130.00 101.83   82
 31  ω    -88.00 -63.00   0.50    8.00    --  -79.25 116.00-154.74   50
 32  ω   -115.00 -90.00   0.50    8.00    --  -79.25 -76.00-135.42   50
 33  ω   -114.00 -89.00   0.50    8.00    --  -79.25 -78.00 114.79   50
 34  ω     71.00 119.00   0.50    8.00    --   80.75   1.00 143.58   96
 35  ω     74.00 125.00   0.50    8.00    --   80.75  19.00 -88.44  102
 36  ω     48.00 102.00   0.50    8.00    --   80.75   1.00-145.26  108
 37  ω     39.00  69.00   0.50    8.00    --   80.75 -61.00 113.65   60
 38  ω     45.00  91.00   0.50    8.00    --   80.75   4.00 -60.17   92
 39  ω     65.00 122.00   0.50    8.00    --   80.75  20.00-153.62  114
 40  ω     43.00  90.00   0.50    8.00    --   80.75-110.00 114.93   94
 41  ω     71.00 106.00   0.50    8.00    --   80.75  22.00-120.40   70
 42  ω     50.00 125.00   0.50    8.00    --   80.75  13.00  44.32  150
 43  ω     66.00 107.00   0.50    8.00    --   80.75  14.00-174.21   82
 44  ω     94.00 124.00   0.50    8.00    --   80.75  43.00 -89.76   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0124407000
_diffrn_orient_matrix_UB_12      0.0524140000
_diffrn_orient_matrix_UB_13      0.0310130000
_diffrn_orient_matrix_UB_21      0.0872615000
_diffrn_orient_matrix_UB_22      -0.0090158000
_diffrn_orient_matrix_UB_23      0.1182854000
_diffrn_orient_matrix_UB_31      0.1083767000
_diffrn_orient_matrix_UB_32      0.0132904000
_diffrn_orient_matrix_UB_33      -0.0421263000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5525
_reflns_number_total             7927
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         7927
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.010
_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)+(0.0498P)²+1.3340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1116
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C81(H81), C1(H1), C11(H11), C82(H82), C2(H2), C24(H24), C30(H30),
 C5(H5), C342(H342), C17(H17), C142(H142), C4(H4), C72(H72), C18(H18), C21(H21),
  C262(H262), C91(H91), C152(H152), C20(H20), C37(H37), C271(H271), C331(H331),
 C71(H71), C36(H36), C141(H141), C341(H341), C151(H151), C272(H272), C332(H332),
  C281(H281), C261(H261)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O4 O 0.20585(11) 0.60570(4) 0.14122(10) 0.0308(3) Uani 1 1 d . . . . .
O2 O 0.65228(11) 0.53293(4) 0.14992(10) 0.0317(3) Uani 1 1 d . . . . .
O1 O 0.16490(11) 0.55597(5) 0.30546(10) 0.0332(3) Uani 1 1 d . . . . .
O3 O 0.70140(11) 0.58759(5) -0.00439(10) 0.0330(3) Uani 1 1 d . . . . .
N1 N 0.29958(14) 0.57017(6) 0.48352(12) 0.0317(3) Uani 1 1 d . . . . .
N4 N 0.36911(13) 0.65806(5) 0.18752(12) 0.0295(3) Uani 1 1 d . . . . .
N3 N 0.72545(14) 0.66866(6) 0.03849(13) 0.0351(4) Uani 1 1 d . . . . .
N2 N 0.64160(13) 0.56832(5) 0.31578(12) 0.0299(3) Uani 1 1 d . . . . .
C6 C 0.20912(17) 0.54155(7) 0.41524(16) 0.0344(4) Uani 1 1 d . . . . .
C23 C 0.71866(18) 0.58343(8) -0.17777(17) 0.0406(5) Uani 1 1 d . . . . .
H23 H 0.723859 0.571295 -0.247252 0.049 Uiso 1 1 calc R U . . .
C25 C 0.71454(17) 0.63277(7) -0.04057(16) 0.0352(4) Uani 1 1 d . . . . .
C81 C 0.39358(18) 0.66292(7) 0.69066(15) 0.0359(4) Uani 1 1 d . . . . .
H81 H 0.464187 0.681709 0.720660 0.043 Uiso 1 1 calc R U . . .
C35 C 0.27452(16) 0.63756(6) 0.10388(15) 0.0295(4) Uani 1 1 d . . . . .
C1 C 0.02140(17) 0.55889(7) 0.05564(17) 0.0376(5) Uani 1 1 d . . . . .
H1 H -0.041924 0.555575 -0.012899 0.045 Uiso 1 1 calc R U . . .
C3 C 0.07153(17) 0.52565(7) 0.25374(17) 0.0366(4) Uani 1 1 d . . . . .
C16 C 0.62636(16) 0.52777(7) 0.24949(14) 0.0299(4) Uani 1 1 d . . . . .
C10 C 0.41252(16) 0.57999(7) 0.46758(15) 0.0302(4) Uani 1 1 d . . . . .
C22 C 0.70345(17) 0.55751(7) -0.09086(15) 0.0347(4) Uani 1 1 d . . . . .
C11 C 0.46161(17) 0.56008(7) 0.38863(15) 0.0316(4) Uani 1 1 d . . . . .
H11 H 0.421956 0.535659 0.338421 0.038 Uiso 1 1 calc R U . . .
C8 C 0.38915(17) 0.62849(7) 0.60816(15) 0.0324(4) Uani 1 1 d . . . . .
C31 C 0.48137(16) 0.67187(6) 0.17450(15) 0.0299(4) Uani 1 1 d . . . . .
C82 C 0.29275(18) 0.66884(8) 0.72724(16) 0.0392(5) Uani 1 1 d . . . . .
H82 H 0.293820 0.692304 0.782334 0.047 Uiso 1 1 calc R U . . .
C2 C 0.00478(18) 0.53138(7) 0.13865(17) 0.0386(5) Uani 1 1 d . . . . .
H2 H -0.065619 0.511961 0.115492 0.046 Uiso 1 1 calc R U . . .
C24 C 0.72531(19) 0.63194(8) -0.14529(17) 0.0425(5) Uani 1 1 d . . . . .
H24 H 0.735340 0.658553 -0.188637 0.051 Uiso 1 1 calc R U . . .
C30 C 0.53639(16) 0.65616(6) 0.09607(15) 0.0312(4) Uani 1 1 d . . . . .
H30 H 0.500120 0.633307 0.040011 0.037 Uiso 1 1 calc R U . . .
C5 C 0.1476(2) 0.50336(8) 0.43466(19) 0.0456(5) Uani 1 1 d . . . . .
H5 H 0.161434 0.486624 0.503490 0.055 Uiso 1 1 calc R U . . .
C342 C 0.26456(18) 0.70733(7) 0.42088(16) 0.0362(4) Uani 1 1 d . . . . .
H342 H 0.199923 0.706634 0.453385 0.043 Uiso 1 1 calc R U . . .
C17 C 0.59280(17) 0.48303(7) 0.26320(16) 0.0330(4) Uani 1 1 d . . . . .
H17 H 0.568218 0.471033 0.324225 0.040 Uiso 1 1 calc R U . . .
C12 C 0.57309(16) 0.57871(6) 0.38898(14) 0.0291(4) Uani 1 1 d . . . . .
C15 C 0.74613(16) 0.59723(6) 0.34494(15) 0.0294(4) Uani 1 1 d . . . . .
C29 C 0.64893(17) 0.67654(7) 0.10610(16) 0.0317(4) Uani 1 1 d . . . . .
C38 C 0.11261(16) 0.59183(7) 0.04760(16) 0.0333(4) Uani 1 1 d . . . . .
C33 C 0.45460(17) 0.71103(6) 0.32770(15) 0.0314(4) Uani 1 1 d . . . . .
C19 C 0.63755(17) 0.48815(7) 0.10070(16) 0.0326(4) Uani 1 1 d . . . . .
C142 C 0.93082(17) 0.66114(7) 0.43104(17) 0.0382(5) Uani 1 1 d . . . . .
H142 H 0.995240 0.683054 0.459660 0.046 Uiso 1 1 calc R U . . .
C4 C 0.0578(2) 0.49317(8) 0.33132(19) 0.0475(5) Uani 1 1 d . . . . .
H4 H -0.000825 0.468446 0.318352 0.057 Uiso 1 1 calc R U . . .
C72 C 0.18940(19) 0.64091(8) 0.68459(17) 0.0408(5) Uani 1 1 d . . . . .
H72 H 0.121545 0.645806 0.711498 0.049 Uiso 1 1 calc R U . . .
C27 C 0.81920(17) 0.72331(7) 0.17196(17) 0.0368(4) Uani 1 1 d . . . . .
C18 C 0.60145(17) 0.45727(7) 0.16812(16) 0.0353(4) Uani 1 1 d . . . . .
H18 H 0.584966 0.424355 0.154135 0.042 Uiso 1 1 calc R U . . .
C13 C 0.63429(16) 0.61471(7) 0.46426(15) 0.0298(4) Uani 1 1 d . . . . .
C21 C 0.68872(17) 0.50732(7) -0.08147(16) 0.0364(4) Uani 1 1 d . . . . .
H21 H 0.701092 0.489818 -0.142275 0.044 Uiso 1 1 calc R U . . .
C14 C 0.74353(16) 0.62618(7) 0.43582(15) 0.0305(4) Uani 1 1 d . . . . .
C262 C 1.02727(19) 0.72775(8) 0.1059(2) 0.0485(6) Uani 1 1 d . . . . .
H262 H 1.099308 0.729813 0.084222 0.058 Uiso 1 1 calc R U . . .
C91 C 0.58275(17) 0.63334(7) 0.54300(15) 0.0321(4) Uani 1 1 d . . . . .
H91 H 0.622858 0.657455 0.593953 0.039 Uiso 1 1 calc R U . . .
C152 C 0.93169(17) 0.63183(7) 0.34114(17) 0.0373(5) Uani 1 1 d . . . . .
H152 H 0.997167 0.634077 0.309957 0.045 Uiso 1 1 calc R U . . .
C20 C 0.66087(17) 0.47957(7) -0.00414(16) 0.0360(4) Uani 1 1 d . . . . .
H20 H 0.655543 0.446827 -0.023895 0.043 Uiso 1 1 calc R U . . .
C37 C 0.12732(18) 0.61403(7) -0.04394(16) 0.0393(5) Uani 1 1 d . . . . .
H37 H 0.076902 0.610403 -0.119037 0.047 Uiso 1 1 calc R U . . .
C271 C 0.91500(18) 0.75239(7) 0.23128(19) 0.0426(5) Uani 1 1 d . . . . .
H271 H 0.909351 0.770561 0.293739 0.051 Uiso 1 1 calc R U . . .
C331 C 0.46075(18) 0.73810(7) 0.42315(16) 0.0363(4) Uani 1 1 d . . . . .
H331 H 0.529270 0.757588 0.456309 0.044 Uiso 1 1 calc R U . . .
C71 C 0.18296(18) 0.60622(7) 0.60403(16) 0.0366(4) Uani 1 1 d . . . . .
H71 H 0.112806 0.586990 0.575879 0.044 Uiso 1 1 calc R U . . .
C7 C 0.28342(17) 0.60094(7) 0.56664(15) 0.0315(4) Uani 1 1 d . . . . .
C36 C 0.23098(18) 0.64357(7) -0.00800(16) 0.0388(5) Uani 1 1 d . . . . .
H36 H 0.263221 0.663544 -0.053530 0.047 Uiso 1 1 calc R U . . .
C141 C 0.83724(17) 0.65874(7) 0.47924(16) 0.0361(4) Uani 1 1 d . . . . .
H141 H 0.836818 0.678789 0.540436 0.043 Uiso 1 1 calc R U . . .
C341 C 0.25698(17) 0.67974(7) 0.32674(16) 0.0333(4) Uani 1 1 d . . . . .
H341 H 0.188811 0.659944 0.294536 0.040 Uiso 1 1 calc R U . . .
C151 C 0.83965(17) 0.59956(7) 0.29622(16) 0.0337(4) Uani 1 1 d . . . . .
H151 H 0.840317 0.579801 0.234624 0.040 Uiso 1 1 calc R U . . .
C272 C 1.01796(19) 0.75410(8) 0.1970(2) 0.0488(6) Uani 1 1 d . . . . .
H272 H 1.083820 0.773713 0.236555 0.059 Uiso 1 1 calc R U . . .
C332 C 0.36494(18) 0.73599(7) 0.46858(16) 0.0381(5) Uani 1 1 d . . . . .
H332 H 0.367878 0.754386 0.533224 0.046 Uiso 1 1 calc R U . . .
C28 C 0.70457(17) 0.71076(7) 0.18890(16) 0.0339(4) Uani 1 1 d . . . . .
C281 C 0.64833(17) 0.72461(7) 0.26736(16) 0.0346(4) Uani 1 1 d . . . . .
H281 H 0.685599 0.746942 0.324349 0.042 Uiso 1 1 calc R U . . .
C26 C 0.83055(17) 0.69668(7) 0.08064(17) 0.0367(4) Uani 1 1 d . . . . .
C9 C 0.47113(17) 0.61568(7) 0.54489(15) 0.0305(4) Uani 1 1 d . . . . .
C34 C 0.35294(16) 0.68225(6) 0.28164(15) 0.0302(4) Uani 1 1 d . . . . .
C32 C 0.53581(16) 0.70505(6) 0.26082(15) 0.0307(4) Uani 1 1 d . . . . .
C261 C 0.93405(18) 0.69853(8) 0.04577(19) 0.0429(5) Uani 1 1 d . . . . .
H261 H 0.940543 0.680517 -0.016614 0.051 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
O4 C35 1.367(2) . ?
O4 C38 1.388(2) . ?
O2 C16 1.369(2) . ?
O2 C19 1.388(2) . ?
O1 C6 1.373(2) . ?
O1 C3 1.375(2) . ?
O3 C25 1.371(2) . ?
O3 C22 1.376(2) . ?
N1 C6 1.391(2) . ?
N1 C10 1.404(2) . ?
N1 C7 1.405(2) . ?
N4 C35 1.391(2) . ?
N4 C31 1.409(2) . ?
N4 C34 1.417(2) . ?
N3 C25 1.390(3) . ?
N3 C29 1.409(2) . ?
N3 C26 1.411(2) . ?
N2 C16 1.388(2) . ?
N2 C12 1.406(2) . ?
N2 C15 1.410(2) . ?
C6 C5 1.348(3) . ?
C23 H23 0.9500 . ?
C23 C22 1.360(3) . ?
C23 C24 1.418(3) . ?
C25 C24 1.349(3) . ?
C81 H81 0.9500 . ?
C81 C8 1.402(3) . ?
C81 C82 1.382(3) . ?
C35 C36 1.346(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.351(3) . ?
C1 C38 1.428(3) . ?
C3 C2 1.422(3) . ?
C3 C4 1.374(3) . ?
C16 C17 1.342(3) . ?
C10 C11 1.392(2) . ?
C10 C9 1.416(3) . ?
C22 C21 1.430(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(3) . ?
C8 C7 1.408(3) . ?
C8 C9 1.447(2) . ?
C31 C30 1.388(2) . ?
C31 C32 1.422(3) . ?
C82 H82 0.9500 . ?
C82 C72 1.395(3) . ?
C2 H2 0.9500 . ?
C24 H24 0.9500 . ?
C30 H30 0.9500 . ?
C30 C29 1.392(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.422(3) . ?
C342 H342 0.9500 . ?
C342 C341 1.388(3) . ?
C342 C332 1.392(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.418(3) . ?
C12 C13 1.418(3) . ?
C15 C14 1.403(2) . ?
C15 C151 1.390(3) . ?
C29 C28 1.418(3) . ?
C38 C37 1.356(3) . ?
C33 C331 1.397(3) . ?
C33 C34 1.400(3) . ?
C33 C32 1.439(3) . ?
C19 C18 1.358(3) . ?
C19 C20 1.432(2) . ?
C142 H142 0.9500 . ?
C142 C152 1.394(3) . ?
C142 C141 1.386(3) . ?
C4 H4 0.9500 . ?
C72 H72 0.9500 . ?
C72 C71 1.386(3) . ?
C27 C271 1.397(3) . ?
C27 C28 1.445(3) . ?
C27 C26 1.401(3) . ?
C18 H18 0.9500 . ?
C13 C14 1.445(2) . ?
C13 C91 1.394(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.352(3) . ?
C14 C141 1.398(3) . ?
C262 H262 0.9500 . ?
C262 C272 1.388(3) . ?
C262 C261 1.384(3) . ?
C91 H91 0.9500 . ?
C91 C9 1.388(3) . ?
C152 H152 0.9500 . ?
C152 C151 1.383(3) . ?
C20 H20 0.9500 . ?
C37 H37 0.9500 . ?
C37 C36 1.416(3) . ?
C271 H271 0.9500 . ?
C271 C272 1.379(3) . ?
C331 H331 0.9500 . ?
C331 C332 1.387(3) . ?
C71 H71 0.9500 . ?
C71 C7 1.381(3) . ?
C36 H36 0.9500 . ?
C141 H141 0.9500 . ?
C341 H341 0.9500 . ?
C341 C34 1.386(3) . ?
C151 H151 0.9500 . ?
C272 H272 0.9500 . ?
C332 H332 0.9500 . ?
C28 C281 1.382(3) . ?
C281 H281 0.9500 . ?
C281 C32 1.391(3) . ?
C26 C261 1.390(3) . ?
C261 H261 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
C35 O4 C38 106.30(14) . . ?
C16 O2 C19 105.92(14) . . ?
C6 O1 C3 106.99(15) . . ?
C25 O3 C22 106.34(14) . . ?
C6 N1 C10 125.95(15) . . ?
C6 N1 C7 124.57(15) . . ?
C10 N1 C7 108.47(15) . . ?
C35 N4 C31 124.89(15) . . ?
C35 N4 C34 123.55(15) . . ?
C31 N4 C34 108.44(14) . . ?
C25 N3 C29 126.75(16) . . ?
C25 N3 C26 123.76(16) . . ?
C29 N3 C26 108.22(16) . . ?
C16 N2 C12 124.16(15) . . ?
C16 N2 C15 125.00(15) . . ?
C12 N2 C15 108.49(14) . . ?
O1 C6 N1 115.40(16) . . ?
C5 C6 O1 110.77(17) . . ?
C5 C6 N1 133.66(18) . . ?
C22 C23 H23 126.4 . . ?
C22 C23 C24 107.22(18) . . ?
C24 C23 H23 126.4 . . ?
O3 C25 N3 115.71(16) . . ?
C24 C25 O3 110.73(18) . . ?
C24 C25 N3 133.23(19) . . ?
C8 C81 H81 120.8 . . ?
C82 C81 H81 120.8 . . ?
C82 C81 C8 118.38(19) . . ?
O4 C35 N4 114.92(15) . . ?
C36 C35 O4 111.11(16) . . ?
C36 C35 N4 133.90(18) . . ?
C2 C1 H1 112.8 . . ?
C2 C1 C38 134.50(19) . . ?
C38 C1 H1 112.8 . . ?
O1 C3 C2 121.16(18) . . ?
C4 C3 O1 108.66(18) . . ?
C4 C3 C2 130.17(19) . . ?
O2 C16 N2 115.50(15) . . ?
C17 C16 O2 111.37(16) . . ?
C17 C16 N2 133.12(17) . . ?
N1 C10 C9 108.58(15) . . ?
C11 C10 N1 127.78(17) . . ?
C11 C10 C9 123.63(17) . . ?
O3 C22 C21 120.76(17) . . ?
C23 C22 O3 109.41(18) . . ?
C23 C22 C21 129.82(19) . . ?
C10 C11 H11 122.6 . . ?
C12 C11 C10 114.77(17) . . ?
C12 C11 H11 122.6 . . ?
C81 C8 C7 119.18(17) . . ?
C81 C8 C9 133.24(19) . . ?
C7 C8 C9 107.42(16) . . ?
N4 C31 C32 107.95(16) . . ?
C30 C31 N4 128.61(17) . . ?
C30 C31 C32 123.41(17) . . ?
C81 C82 H82 119.5 . . ?
C81 C82 C72 121.07(19) . . ?
C72 C82 H82 119.5 . . ?
C1 C2 C3 132.88(19) . . ?
C1 C2 H2 113.6 . . ?
C3 C2 H2 113.6 . . ?
C23 C24 H24 126.8 . . ?
C25 C24 C23 106.30(18) . . ?
C25 C24 H24 126.8 . . ?
C31 C30 H30 122.7 . . ?
C31 C30 C29 114.65(17) . . ?
C29 C30 H30 122.7 . . ?
C6 C5 H5 126.9 . . ?
C6 C5 C4 106.16(19) . . ?
C4 C5 H5 126.9 . . ?
C341 C342 H342 119.3 . . ?
C341 C342 C332 121.32(19) . . ?
C332 C342 H342 119.3 . . ?
C16 C17 H17 127.0 . . ?
C16 C17 C18 106.06(16) . . ?
C18 C17 H17 127.0 . . ?
N2 C12 C13 108.20(15) . . ?
C11 C12 N2 128.35(17) . . ?
C11 C12 C13 123.37(16) . . ?
C14 C15 N2 108.66(15) . . ?
C151 C15 N2 129.16(17) . . ?
C151 C15 C14 122.17(17) . . ?
N3 C29 C28 108.28(16) . . ?
C30 C29 N3 128.10(17) . . ?
C30 C29 C28 123.61(17) . . ?
O4 C38 C1 121.77(17) . . ?
C37 C38 O4 108.62(16) . . ?
C37 C38 C1 129.61(18) . . ?
C331 C33 C34 119.20(17) . . ?
C331 C33 C32 132.95(18) . . ?
C34 C33 C32 107.84(16) . . ?
O2 C19 C20 121.65(17) . . ?
C18 C19 O2 108.97(16) . . ?
C18 C19 C20 129.37(18) . . ?
C152 C142 H142 119.5 . . ?
C141 C142 H142 119.5 . . ?
C141 C142 C152 120.92(19) . . ?
C3 C4 C5 107.40(19) . . ?
C3 C4 H4 126.3 . . ?
C5 C4 H4 126.3 . . ?
C82 C72 H72 119.1 . . ?
C71 C72 C82 121.83(18) . . ?
C71 C72 H72 119.1 . . ?
C271 C27 C28 132.9(2) . . ?
C271 C27 C26 119.46(18) . . ?
C26 C27 C28 107.47(17) . . ?
C17 C18 H18 126.2 . . ?
C19 C18 C17 107.64(17) . . ?
C19 C18 H18 126.2 . . ?
C12 C13 C14 107.23(15) . . ?
C91 C13 C12 120.11(17) . . ?
C91 C13 C14 132.60(17) . . ?
C22 C21 H21 113.3 . . ?
C20 C21 C22 133.40(18) . . ?
C20 C21 H21 113.3 . . ?
C15 C14 C13 107.42(16) . . ?
C141 C14 C15 119.51(17) . . ?
C141 C14 C13 133.07(17) . . ?
C272 C262 H262 119.2 . . ?
C261 C262 H262 119.2 . . ?
C261 C262 C272 121.5(2) . . ?
C13 C91 H91 120.9 . . ?
C9 C91 C13 118.13(17) . . ?
C9 C91 H91 120.9 . . ?
C142 C152 H152 119.2 . . ?
C151 C152 C142 121.65(18) . . ?
C151 C152 H152 119.2 . . ?
C19 C20 H20 112.6 . . ?
C21 C20 C19 134.77(19) . . ?
C21 C20 H20 112.6 . . ?
C38 C37 H37 126.0 . . ?
C38 C37 C36 108.02(17) . . ?
C36 C37 H37 126.0 . . ?
C27 C271 H271 120.8 . . ?
C272 C271 C27 118.4(2) . . ?
C272 C271 H271 120.8 . . ?
C33 C331 H331 120.6 . . ?
C332 C331 C33 118.74(19) . . ?
C332 C331 H331 120.6 . . ?
C72 C71 H71 121.6 . . ?
C7 C71 C72 116.82(19) . . ?
C7 C71 H71 121.6 . . ?
N1 C7 C8 108.58(15) . . ?
C71 C7 N1 128.68(18) . . ?
C71 C7 C8 122.72(18) . . ?
C35 C36 C37 105.94(17) . . ?
C35 C36 H36 127.0 . . ?
C37 C36 H36 127.0 . . ?
C142 C141 C14 118.52(18) . . ?
C142 C141 H141 120.7 . . ?
C14 C141 H141 120.7 . . ?
C342 C341 H341 121.4 . . ?
C34 C341 C342 117.28(18) . . ?
C34 C341 H341 121.4 . . ?
C15 C151 H151 121.4 . . ?
C152 C151 C15 117.23(18) . . ?
C152 C151 H151 121.4 . . ?
C262 C272 H272 119.3 . . ?
C271 C272 C262 121.3(2) . . ?
C271 C272 H272 119.3 . . ?
C342 C332 H332 119.5 . . ?
C331 C332 C342 120.98(18) . . ?
C331 C332 H332 119.5 . . ?
C29 C28 C27 107.17(17) . . ?
C281 C28 C29 120.02(17) . . ?
C281 C28 C27 132.78(18) . . ?
C28 C281 H281 120.8 . . ?
C28 C281 C32 118.37(17) . . ?
C32 C281 H281 120.8 . . ?
C27 C26 N3 108.83(16) . . ?
C261 C26 N3 129.0(2) . . ?
C261 C26 C27 122.14(19) . . ?
C10 C9 C8 106.85(16) . . ?
C91 C9 C10 119.98(16) . . ?
C91 C9 C8 133.01(18) . . ?
C33 C34 N4 108.42(16) . . ?
C341 C34 N4 129.10(17) . . ?
C341 C34 C33 122.48(17) . . ?
C31 C32 C33 107.35(16) . . ?
C281 C32 C31 119.89(17) . . ?
C281 C32 C33 132.76(17) . . ?
C262 C261 C26 117.1(2) . . ?
C262 C261 H261 121.4 . . ?
C26 C261 H261 121.4 . . ?

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
O4 C35 C36 C37 0.6(2) . . . . ?
O4 C38 C37 C36 -1.2(2) . . . . ?
O2 C16 C17 C18 2.0(2) . . . . ?
O2 C19 C18 C17 0.0(2) . . . . ?
O2 C19 C20 C21 -6.3(3) . . . . ?
O1 C6 C5 C4 -0.7(2) . . . . ?
O1 C3 C2 C1 10.0(3) . . . . ?
O1 C3 C4 C5 -1.0(2) . . . . ?
O3 C25 C24 C23 0.0(2) . . . . ?
O3 C22 C21 C20 6.9(3) . . . . ?
N1 C6 C5 C4 174.2(2) . . . . ?
N1 C10 C11 C12 176.72(17) . . . . ?
N1 C10 C9 C8 -1.2(2) . . . . ?
N1 C10 C9 C91 -177.16(16) . . . . ?
N4 C35 C36 C37 -176.1(2) . . . . ?
N4 C31 C30 C29 -179.37(17) . . . . ?
N4 C31 C32 C33 0.4(2) . . . . ?
N4 C31 C32 C281 -179.89(16) . . . . ?
N3 C25 C24 C23 172.9(2) . . . . ?
N3 C29 C28 C27 -1.0(2) . . . . ?
N3 C29 C28 C281 -179.36(17) . . . . ?
N3 C26 C261 C262 -176.88(19) . . . . ?
N2 C16 C17 C18 -176.58(19) . . . . ?
N2 C12 C13 C14 -0.3(2) . . . . ?
N2 C12 C13 C91 177.01(16) . . . . ?
N2 C15 C14 C13 0.3(2) . . . . ?
N2 C15 C14 C141 -179.03(16) . . . . ?
N2 C15 C151 C152 179.30(18) . . . . ?
C6 O1 C3 C2 179.17(17) . . . . ?
C6 O1 C3 C4 0.5(2) . . . . ?
C6 N1 C10 C11 -6.7(3) . . . . ?
C6 N1 C10 C9 171.69(17) . . . . ?
C6 N1 C7 C8 -172.41(17) . . . . ?
C6 N1 C7 C71 6.1(3) . . . . ?
C6 C5 C4 C3 1.0(3) . . . . ?
C23 C22 C21 C20 -171.9(2) . . . . ?
C25 O3 C22 C23 0.6(2) . . . . ?
C25 O3 C22 C21 -178.43(17) . . . . ?
C25 N3 C29 C30 -12.1(3) . . . . ?
C25 N3 C29 C28 169.19(17) . . . . ?
C25 N3 C26 C27 -169.75(17) . . . . ?
C25 N3 C26 C261 7.9(3) . . . . ?
C81 C8 C7 N1 178.44(16) . . . . ?
C81 C8 C7 C71 -0.2(3) . . . . ?
C81 C8 C9 C10 -175.9(2) . . . . ?
C81 C8 C9 C91 -0.7(4) . . . . ?
C81 C82 C72 C71 -0.1(3) . . . . ?
C35 O4 C38 C1 -179.09(17) . . . . ?
C35 O4 C38 C37 1.5(2) . . . . ?
C35 N4 C31 C30 -21.8(3) . . . . ?
C35 N4 C31 C32 160.35(17) . . . . ?
C35 N4 C34 C33 -160.97(16) . . . . ?
C35 N4 C34 C341 19.6(3) . . . . ?
C1 C38 C37 C36 179.5(2) . . . . ?
C3 O1 C6 N1 -175.80(16) . . . . ?
C3 O1 C6 C5 0.1(2) . . . . ?
C16 O2 C19 C18 1.2(2) . . . . ?
C16 O2 C19 C20 -178.04(17) . . . . ?
C16 N2 C12 C11 -19.2(3) . . . . ?
C16 N2 C12 C13 163.80(16) . . . . ?
C16 N2 C15 C14 -163.62(16) . . . . ?
C16 N2 C15 C151 17.1(3) . . . . ?
C16 C17 C18 C19 -1.2(2) . . . . ?
C10 N1 C6 O1 -60.0(2) . . . . ?
C10 N1 C6 C5 125.2(2) . . . . ?
C10 N1 C7 C8 -3.3(2) . . . . ?
C10 N1 C7 C71 175.21(19) . . . . ?
C10 C11 C12 N2 -175.70(17) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C22 O3 C25 N3 -174.62(15) . . . . ?
C22 O3 C25 C24 -0.3(2) . . . . ?
C22 C23 C24 C25 0.4(2) . . . . ?
C22 C21 C20 C19 -1.8(4) . . . . ?
C11 C10 C9 C8 177.27(17) . . . . ?
C11 C10 C9 C91 1.3(3) . . . . ?
C11 C12 C13 C14 -177.47(17) . . . . ?
C11 C12 C13 C91 -0.1(3) . . . . ?
C8 C81 C82 C72 0.9(3) . . . . ?
C31 N4 C35 O4 147.38(16) . . . . ?
C31 N4 C35 C36 -36.0(3) . . . . ?
C31 N4 C34 C33 -0.2(2) . . . . ?
C31 N4 C34 C341 -179.61(18) . . . . ?
C31 C30 C29 N3 -178.72(17) . . . . ?
C31 C30 C29 C28 -0.2(3) . . . . ?
C82 C81 C8 C7 -0.7(3) . . . . ?
C82 C81 C8 C9 173.9(2) . . . . ?
C82 C72 C71 C7 -0.8(3) . . . . ?
C2 C1 C38 O4 -7.2(3) . . . . ?
C2 C1 C38 C37 172.0(2) . . . . ?
C2 C3 C4 C5 -179.4(2) . . . . ?
C24 C23 C22 O3 -0.6(2) . . . . ?
C24 C23 C22 C21 178.31(19) . . . . ?
C30 C31 C32 C33 -177.62(17) . . . . ?
C30 C31 C32 C281 2.1(3) . . . . ?
C30 C29 C28 C27 -179.82(17) . . . . ?
C30 C29 C28 C281 1.8(3) . . . . ?
C342 C341 C34 N4 179.60(17) . . . . ?
C342 C341 C34 C33 0.2(3) . . . . ?
C12 N2 C16 O2 149.44(16) . . . . ?
C12 N2 C16 C17 -32.0(3) . . . . ?
C12 N2 C15 C14 -0.5(2) . . . . ?
C12 N2 C15 C151 -179.75(18) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C12 C13 C14 C141 179.2(2) . . . . ?
C12 C13 C91 C9 -0.1(3) . . . . ?
C15 N2 C16 O2 -50.0(2) . . . . ?
C15 N2 C16 C17 128.6(2) . . . . ?
C15 N2 C12 C11 177.46(18) . . . . ?
C15 N2 C12 C13 0.49(19) . . . . ?
C15 C14 C141 C142 -0.4(3) . . . . ?
C29 N3 C25 O3 -50.2(3) . . . . ?
C29 N3 C25 C24 137.1(2) . . . . ?
C29 N3 C26 C27 -1.9(2) . . . . ?
C29 N3 C26 C261 175.76(19) . . . . ?
C29 C28 C281 C32 -1.5(3) . . . . ?
C38 O4 C35 N4 176.06(15) . . . . ?
C38 O4 C35 C36 -1.3(2) . . . . ?
C38 C1 C2 C3 2.4(4) . . . . ?
C38 C37 C36 C35 0.4(2) . . . . ?
C33 C331 C332 C342 0.4(3) . . . . ?
C19 O2 C16 N2 176.86(15) . . . . ?
C19 O2 C16 C17 -2.0(2) . . . . ?
C142 C152 C151 C15 -0.4(3) . . . . ?
C4 C3 C2 C1 -171.7(2) . . . . ?
C72 C71 C7 N1 -177.39(18) . . . . ?
C72 C71 C7 C8 1.0(3) . . . . ?
C27 C271 C272 C262 0.0(3) . . . . ?
C27 C28 C281 C32 -179.36(19) . . . . ?
C27 C26 C261 C262 0.5(3) . . . . ?
C18 C19 C20 C21 174.7(2) . . . . ?
C13 C14 C141 C142 -179.49(19) . . . . ?
C13 C91 C9 C10 -0.5(3) . . . . ?
C13 C91 C9 C8 -175.21(19) . . . . ?
C14 C15 C151 C152 0.1(3) . . . . ?
C14 C13 C91 C9 176.47(19) . . . . ?
C91 C13 C14 C15 -176.83(19) . . . . ?
C91 C13 C14 C141 2.3(4) . . . . ?
C152 C142 C141 C14 0.1(3) . . . . ?
C20 C19 C18 C17 179.14(19) . . . . ?
C271 C27 C28 C29 -175.3(2) . . . . ?
C271 C27 C28 C281 2.8(4) . . . . ?
C271 C27 C26 N3 177.14(17) . . . . ?
C271 C27 C26 C261 -0.7(3) . . . . ?
C331 C33 C34 N4 -179.06(16) . . . . ?
C331 C33 C34 C341 0.4(3) . . . . ?
C331 C33 C32 C31 178.9(2) . . . . ?
C331 C33 C32 C281 -0.8(4) . . . . ?
C7 N1 C6 O1 107.19(19) . . . . ?
C7 N1 C6 C5 -67.6(3) . . . . ?
C7 N1 C10 C11 -175.59(18) . . . . ?
C7 N1 C10 C9 2.8(2) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
C7 C8 C9 C91 174.4(2) . . . . ?
C141 C142 C152 C151 0.3(3) . . . . ?
C341 C342 C332 C331 0.3(3) . . . . ?
C151 C15 C14 C13 179.61(17) . . . . ?
C151 C15 C14 C141 0.3(3) . . . . ?
C272 C262 C261 C26 0.0(3) . . . . ?
C332 C342 C341 C34 -0.6(3) . . . . ?
C28 C27 C271 C272 175.1(2) . . . . ?
C28 C27 C26 N3 1.2(2) . . . . ?
C28 C27 C26 C261 -176.60(18) . . . . ?
C28 C281 C32 C31 -0.3(3) . . . . ?
C28 C281 C32 C33 179.31(19) . . . . ?
C26 N3 C25 O3 115.33(19) . . . . ?
C26 N3 C25 C24 -57.3(3) . . . . ?
C26 N3 C29 C30 -179.48(18) . . . . ?
C26 N3 C29 C28 1.8(2) . . . . ?
C26 C27 C271 C272 0.4(3) . . . . ?
C26 C27 C28 C29 -0.1(2) . . . . ?
C26 C27 C28 C281 177.9(2) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
C9 C8 C7 N1 2.6(2) . . . . ?
C9 C8 C7 C71 -176.09(17) . . . . ?
C34 N4 C35 O4 -55.0(2) . . . . ?
C34 N4 C35 C36 121.7(2) . . . . ?
C34 N4 C31 C30 177.72(18) . . . . ?
C34 N4 C31 C32 -0.16(19) . . . . ?
C34 C33 C331 C332 -0.7(3) . . . . ?
C34 C33 C32 C31 -0.5(2) . . . . ?
C34 C33 C32 C281 179.85(19) . . . . ?
C32 C31 C30 C29 -1.8(3) . . . . ?
C32 C33 C331 C332 179.99(19) . . . . ?
C32 C33 C34 N4 0.4(2) . . . . ?
C32 C33 C34 C341 179.90(17) . . . . ?
C261 C262 C272 C271 -0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.461
_oxdiff_exptl_absorpt_empirical_full_min 0.841
####################################################################### 
# 
# 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_MJP_KD_AD00143_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2373298'
loop_
_audit_author_name
_audit_author_address
'Milosz Pawlicki'
;Faculty of Chemistry, Jagiellonian University
Poland
;
_audit_update_record             
;
2024-07-24 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_audit_creation_date             2024-04-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
loop_
_audit_author_email
''
krzysztof.dzieszkowski@uj.edu.pl
_chemical_formula_moiety         'C34 H28 N2 O4'
_chemical_formula_sum            'C34 H28 N2 O4'
_chemical_formula_weight         528.612
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   10.0198(3)
_cell_length_b                   11.0048(3)
_cell_length_c                   12.9519(4)
_cell_angle_alpha                94.415(1)
_cell_angle_beta                 94.158(1)
_cell_angle_gamma                113.090(1)
_cell_volume                     1301.61(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9151
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      36.39
_cell_measurement_theta_min      2.71
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.6499
_exptl_absorpt_correction_T_min  0.6090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0818 before and 0.0407 after correction.
The Ratio of minimum to maximum transmission is 0.9371.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       prism
_exptl_crystal_F_000             556.353
_exptl_crystal_recrystallization_method 
'slow evaporation from DCM/hexane mixture'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.9781
_diffrn_reflns_Laue_measured_fraction_max 0.9896
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            48454
_diffrn_reflns_point_group_measured_fraction_full 0.9781
_diffrn_reflns_point_group_measured_fraction_max 0.9896
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         33.14
_diffrn_reflns_theta_min         2.71
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.9781
_diffrn_measured_fraction_theta_max 0.9896
_diffrn_measurement_device_type  'D8Quest Eco Photon50'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                9020
_reflns_number_total             9800
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.1927
_refine_diff_density_min         -0.1945
_refine_diff_density_rms         0.0266
_refine_ls_d_res_high            0.6500
_refine_ls_d_res_low             7.5075
_refine_ls_goodness_of_fit_ref   1.0908
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     445
_refine_ls_number_reflns         9800
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0190
_refine_ls_restrained_S_all      1.0908
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0132P)²+0.0812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0410
_refine_ls_wR_factor_ref         0.0421
_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
;
_olex2_refine_details            
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      cc-pVDZ
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2023-08-21_15-20-50
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O001 O 0.46675(3) 0.82250(3) 0.50998(2) 0.01360(5) Uani 1.000000 .
O002 O 0.46290(3) 0.79469(3) 0.07055(2) 0.01499(5) Uani 1.000000 .
O003 O 0.19258(3) 0.76925(3) 0.40364(2) 0.02084(6) Uani 1.000000 .
O004 O 0.34102(4) 0.88929(4) -0.09252(2) 0.02715(7) Uani 1.000000 .
N005 N 0.70083(3) 0.83921(3) 0.55611(2) 0.01194(5) Uani 1.000000 .
N006 N 0.61350(3) 0.73056(3) 0.17741(2) 0.01220(5) Uani 1.000000 .
C007 C 0.69903(4) 0.75948(3) 0.46348(2) 0.01034(5) Uani 1.000000 .
C008 C 0.88109(4) 0.77656(3) 0.64430(2) 0.01051(5) Uani 1.000000 .
C009 C 0.65287(4) 0.78375(3) 0.36649(2) 0.01138(5) Uani 1.000000 .
H009 H 0.6165(6) 0.8625(5) 0.3603(4) 0.01366(7) Uiso 1.000000 R
C00A C 0.75543(3) 0.66259(3) 0.47348(2) 0.01019(5) Uani 1.000000 .
C00B C 0.76423(4) 0.59070(3) 0.38292(3) 0.01157(5) Uani 1.000000 .
H00B H 0.8079(6) 0.5168(5) 0.3895(4) 0.01388(7) Uiso 1.000000 R
C00C C 0.57948(4) 0.85479(3) 0.58454(3) 0.01213(6) Uani 1.000000 .
C00D C 0.69629(4) 0.71614(3) 0.09578(2) 0.01226(6) Uani 1.000000 .
C00E C 0.82371(4) 0.87223(3) 0.63193(2) 0.01123(5) Uani 1.000000 .
C00F C 0.71320(4) 0.60857(3) 0.28451(2) 0.01094(5) Uani 1.000000 .
C00G C 0.75198(4) 0.61762(4) 0.09957(3) 0.01317(6) Uani 1.000000 .
C00H C 1.07352(4) 0.93878(4) 0.76840(3) 0.01517(6) Uani 1.000000 .
H00H H 1.1703(6) 0.9635(6) 0.8206(4) 0.01820(7) Uiso 1.000000 R
C00I C 0.48824(4) 0.75217(3) 0.16145(3) 0.01256(6) Uani 1.000000 .
C00J C 1.00836(4) 0.81277(4) 0.71247(3) 0.01312(6) Uani 1.000000 .
H00J H 1.0567(6) 0.7431(5) 0.7224(4) 0.01574(7) Uiso 1.000000 R
C00K C 0.79928(4) 0.63980(3) 0.58312(2) 0.01087(5) Uani 1.000000 .
C00L C 0.65683(4) 0.70572(3) 0.27790(2) 0.01075(5) Uani 1.000000 .
C00M C 0.88796(4) 0.99864(3) 0.68686(3) 0.01459(6) Uani 1.000000 .
H00M H 0.8442(6) 1.0707(6) 0.6731(4) 0.01750(7) Uiso 1.000000 R
C00N C 0.71218(4) 0.52549(3) 0.18464(3) 0.01258(6) Uani 1.000000 .
C00O C 0.72842(4) 0.80167(4) 0.01833(3) 0.01602(6) Uani 1.000000 .
H00O H 0.6885(6) 0.8784(6) 0.0186(4) 0.01922(8) Uiso 1.000000 R
C00P C 1.01216(4) 1.03093(4) 0.75632(3) 0.01602(6) Uani 1.000000 .
H00P H 1.0622(6) 1.1286(6) 0.7984(4) 0.01922(8) Uiso 1.000000 R
C00Q C 0.27731(4) 0.77397(4) 0.16419(3) 0.01825(7) Uani 1.000000 .
H00Q H 0.1768(7) 0.7741(6) 0.1875(5) 0.02190(8) Uiso 1.000000 R
C00R C 0.54715(4) 0.89740(4) 0.67898(3) 0.01681(6) Uani 1.000000 .
H00R H 0.6155(6) 0.9268(6) 0.7510(5) 0.02017(8) Uiso 1.000000 R
C00S C 0.88928(4) 0.55573(4) 0.58338(3) 0.01622(6) Uani 1.000000 .
H00A H 0.9883(7) 0.6020(6) 0.5472(5) 0.02433(9) Uiso 1.000000 R
H00C H 0.8267(7) 0.4586(6) 0.5416(5) 0.02433(9) Uiso 1.000000 R
H00D H 0.9165(7) 0.5410(6) 0.6626(5) 0.02433(9) Uiso 1.000000 R
C00T C 0.33227(4) 0.80872(4) 0.07178(3) 0.01685(6) Uani 1.000000 .
C00U C 0.35764(4) 0.84607(4) 0.55640(3) 0.01558(6) Uani 1.000000 .
C00V C 0.65871(4) 0.56523(4) 0.63349(3) 0.01608(6) Uani 1.000000 .
H00E H 0.6854(7) 0.5519(6) 0.7129(5) 0.02412(9) Uiso 1.000000 R
H00F H 0.5999(7) 0.4706(6) 0.5912(5) 0.02412(9) Uiso 1.000000 R
H00G H 0.5885(7) 0.6182(6) 0.6353(5) 0.02412(9) Uiso 1.000000 R
C00W C 0.22371(4) 0.81986(4) 0.49409(3) 0.01745(7) Uani 1.000000 .
H00W H 0.1479(6) 0.8499(6) 0.5354(4) 0.02094(8) Uiso 1.000000 R
C00X C 0.83711(4) 0.60542(4) 0.02209(3) 0.02010(7) Uani 1.000000 .
H00X H 0.8785(7) 0.5303(6) 0.0223(5) 0.02412(9) Uiso 1.000000 R
C00Y C 0.37693(4) 0.73745(4) 0.22296(3) 0.01685(6) Uani 1.000000 .
H00Y H 0.3671(6) 0.7062(6) 0.2987(5) 0.02023(8) Uiso 1.000000 R
C00Z C 0.81561(5) 0.45478(4) 0.19916(3) 0.01930(7) Uani 1.000000 .
H00I H 0.9265(7) 0.5261(6) 0.2213(5) 0.02895(10) Uiso 1.000000 R
H00K H 0.8125(7) 0.3954(6) 0.1279(5) 0.02895(10) Uiso 1.000000 R
H00L H 0.7809(7) 0.3862(6) 0.2565(5) 0.02895(10) Uiso 1.000000 R
C010 C 0.55630(4) 0.41925(4) 0.15256(3) 0.01835(7) Uani 1.000000 .
H01A H 0.5224(7) 0.3525(6) 0.2118(5) 0.02753(10) Uiso 1.000000 R
H01B H 0.5524(7) 0.3607(6) 0.0809(5) 0.02753(10) Uiso 1.000000 R
H01C H 0.4782(7) 0.4646(6) 0.1394(5) 0.02753(10) Uiso 1.000000 R
C011 C 0.81197(4) 0.78617(4) -0.05858(3) 0.02119(7) Uani 1.000000 .
H011 H 0.8360(7) 0.8524(6) -0.1184(5) 0.02542(9) Uiso 1.000000 R
C012 C 0.40449(4) 0.89167(4) 0.65975(3) 0.01787(7) Uani 1.000000 .
H012 H 0.3449(6) 0.9158(6) 0.7162(5) 0.02144(8) Uiso 1.000000 R
C013 C 0.28087(5) 0.85877(4) -0.01427(3) 0.02068(7) Uani 1.000000 .
H013 H 0.1777(7) 0.8682(6) -0.0020(5) 0.02482(9) Uiso 1.000000 R
C014 C 0.86584(5) 0.68768(5) -0.05702(3) 0.02431(8) Uani 1.000000 .
H014 H 0.9306(7) 0.6751(6) -0.1170(5) 0.02917(10) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00C 1.3449(4) . ?
O001 C00U 1.3848(4) . ?
O002 C00I 1.3432(4) . ?
O002 C00T 1.3778(4) . ?
O003 C00W 1.2207(5) . ?
O004 C013 1.2188(5) . ?
N005 C007 1.4254(4) . ?
N005 C00C 1.3647(4) . ?
N005 C00E 1.4252(4) . ?
N006 C00D 1.4268(4) . ?
N006 C00I 1.3706(4) . ?
N006 C00L 1.4224(4) . ?
C007 C009 1.3883(4) . ?
C007 C00A 1.3987(4) . ?
C008 C00E 1.3971(5) . ?
C008 C00J 1.3959(5) . ?
C008 C00K 1.5229(5) . ?
C009 H009 1.069(5) . ?
C009 C00L 1.3918(4) . ?
C00A C00B 1.3914(4) . ?
C00A C00K 1.5243(4) . ?
C00B H00B 1.069(5) . ?
C00B C00F 1.3956(5) . ?
C00C C00R 1.3817(5) . ?
C00D C00G 1.4029(5) . ?
C00D C00O 1.3965(5) . ?
C00E C00M 1.3909(5) . ?
C00F C00L 1.3965(5) . ?
C00F C00N 1.5224(5) . ?
C00G C00N 1.5230(5) . ?
C00G C00X 1.3949(5) . ?
C00H H00H 1.068(6) . ?
C00H C00J 1.3931(5) . ?
C00H C00P 1.3894(5) . ?
C00I C00Y 1.3827(5) . ?
C00J H00J 1.066(5) . ?
C00K C00S 1.5244(5) . ?
C00K C00V 1.5466(5) . ?
C00M H00M 1.066(5) . ?
C00M C00P 1.3877(5) . ?
C00N C00Z 1.5302(5) . ?
C00N C010 1.5420(5) . ?
C00O H00O 1.066(6) . ?
C00O C011 1.3888(5) . ?
C00P H00P 1.072(6) . ?
C00Q H00Q 1.072(6) . ?
C00Q C00T 1.3721(5) . ?
C00Q C00Y 1.4103(5) . ?
C00R H00R 1.063(6) . ?
C00R C012 1.4088(5) . ?
C00S H00A 1.082(6) . ?
C00S H00C 1.079(6) . ?
C00S H00D 1.083(6) . ?
C00T C013 1.4299(5) . ?
C00U C00W 1.4278(5) . ?
C00U C012 1.3728(5) . ?
C00V H00E 1.079(6) . ?
C00V H00F 1.057(6) . ?
C00V H00G 1.076(6) . ?
C00W H00W 1.096(6) . ?
C00X H00X 1.061(6) . ?
C00X C014 1.3905(6) . ?
C00Y H00Y 1.063(6) . ?
C00Z H00I 1.081(6) . ?
C00Z H00K 1.080(6) . ?
C00Z H00L 1.077(6) . ?
C010 H01A 1.083(6) . ?
C010 H01B 1.078(6) . ?
C010 H01C 1.091(6) . ?
C011 H011 1.080(6) . ?
C011 C014 1.3882(6) . ?
C012 H012 1.058(6) . ?
C013 H013 1.100(6) . ?
C014 H014 1.082(6) . ?

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
C00U O001 C00C 106.63(3) . . ?
C00T O002 C00I 107.07(3) . . ?
C00C N005 C007 122.74(3) . . ?
C00E N005 C007 115.82(3) . . ?
C00E N005 C00C 119.32(3) . . ?
C00I N006 C00D 123.63(3) . . ?
C00L N006 C00D 116.58(3) . . ?
C00L N006 C00I 119.40(3) . . ?
C009 C007 N005 121.09(3) . . ?
C00A C007 N005 117.37(3) . . ?
C00A C007 C009 121.39(3) . . ?
C00J C008 C00E 117.71(3) . . ?
C00K C008 C00E 117.55(3) . . ?
C00K C008 C00J 124.74(3) . . ?
H009 C009 C007 120.1(3) . . ?
C00L C009 C007 119.09(3) . . ?
C00L C009 H009 120.8(3) . . ?
C00B C00A C007 117.96(3) . . ?
C00K C00A C007 117.84(3) . . ?
C00K C00A C00B 124.17(3) . . ?
H00B C00B C00A 118.7(3) . . ?
C00F C00B C00A 122.16(3) . . ?
C00F C00B H00B 119.1(3) . . ?
N005 C00C O001 116.93(3) . . ?
C00R C00C O001 111.25(3) . . ?
C00R C00C N005 131.81(3) . . ?
C00G C00D N006 117.45(3) . . ?
C00O C00D N006 121.51(3) . . ?
C00O C00D C00G 120.93(3) . . ?
C008 C00E N005 117.81(3) . . ?
C00M C00E N005 120.26(3) . . ?
C00M C00E C008 121.83(3) . . ?
C00L C00F C00B 118.06(3) . . ?
C00N C00F C00B 123.50(3) . . ?
C00N C00F C00L 118.42(3) . . ?
C00N C00G C00D 119.00(3) . . ?
C00X C00G C00D 117.99(3) . . ?
C00X C00G C00N 122.96(3) . . ?
C00J C00H H00H 119.5(3) . . ?
C00P C00H H00H 120.6(3) . . ?
C00P C00H C00J 119.95(3) . . ?
N006 C00I O002 117.33(3) . . ?
C00Y C00I O002 111.01(3) . . ?
C00Y C00I N006 131.66(3) . . ?
C00H C00J C008 121.08(3) . . ?
H00J C00J C008 119.8(3) . . ?
H00J C00J C00H 119.2(3) . . ?
C00A C00K C008 106.79(3) . . ?
C00S C00K C008 112.31(3) . . ?
C00S C00K C00A 112.51(3) . . ?
C00V C00K C008 108.85(3) . . ?
C00V C00K C00A 108.36(3) . . ?
C00V C00K C00S 107.91(3) . . ?
C009 C00L N006 120.24(3) . . ?
C00F C00L N006 118.39(3) . . ?
C00F C00L C009 121.20(3) . . ?
H00M C00M C00E 119.9(3) . . ?
C00P C00M C00E 119.31(3) . . ?
C00P C00M H00M 120.7(3) . . ?
C00G C00N C00F 107.60(3) . . ?
C00Z C00N C00F 111.64(3) . . ?
C00Z C00N C00G 112.09(3) . . ?
C010 C00N C00F 109.02(3) . . ?
C010 C00N C00G 108.01(3) . . ?
C010 C00N C00Z 108.38(3) . . ?
H00O C00O C00D 119.8(3) . . ?
C011 C00O C00D 119.80(4) . . ?
C011 C00O H00O 120.4(3) . . ?
C00M C00P C00H 120.08(3) . . ?
H00P C00P C00H 120.5(3) . . ?
H00P C00P C00M 119.4(3) . . ?
C00T C00Q H00Q 126.4(3) . . ?
C00Y C00Q H00Q 126.2(3) . . ?
C00Y C00Q C00T 107.48(3) . . ?
H00R C00R C00C 126.9(3) . . ?
C012 C00R C00C 105.48(3) . . ?
C012 C00R H00R 127.6(3) . . ?
H00A C00S C00K 111.3(3) . . ?
H00C C00S C00K 110.3(3) . . ?
H00C C00S H00A 108.5(5) . . ?
H00D C00S C00K 109.9(3) . . ?
H00D C00S H00A 109.6(5) . . ?
H00D C00S H00C 107.1(5) . . ?
C00Q C00T O002 109.09(3) . . ?
C013 C00T O002 119.25(3) . . ?
C013 C00T C00Q 131.60(4) . . ?
C00W C00U O001 118.52(3) . . ?
C012 C00U O001 109.18(3) . . ?
C012 C00U C00W 132.30(3) . . ?
H00E C00V C00K 110.5(3) . . ?
H00F C00V C00K 109.7(3) . . ?
H00F C00V H00E 108.5(5) . . ?
H00G C00V C00K 112.3(3) . . ?
H00G C00V H00E 107.3(5) . . ?
H00G C00V H00F 108.4(5) . . ?
C00U C00W O003 125.15(3) . . ?
H00W C00W O003 121.5(3) . . ?
H00W C00W C00U 113.3(3) . . ?
H00X C00X C00G 119.4(3) . . ?
C014 C00X C00G 121.33(4) . . ?
C014 C00X H00X 119.3(3) . . ?
C00Q C00Y C00I 105.34(3) . . ?
H00Y C00Y C00I 128.2(3) . . ?
H00Y C00Y C00Q 126.4(3) . . ?
H00I C00Z C00N 110.7(3) . . ?
H00K C00Z C00N 110.6(3) . . ?
H00K C00Z H00I 108.6(5) . . ?
H00L C00Z C00N 110.3(3) . . ?
H00L C00Z H00I 110.7(5) . . ?
H00L C00Z H00K 105.8(5) . . ?
H01A C010 C00N 110.6(3) . . ?
H01B C010 C00N 110.3(3) . . ?
H01B C010 H01A 107.9(5) . . ?
H01C C010 C00N 111.4(3) . . ?
H01C C010 H01A 109.3(5) . . ?
H01C C010 H01B 107.3(5) . . ?
H011 C011 C00O 119.4(3) . . ?
C014 C011 C00O 119.99(4) . . ?
C014 C011 H011 120.6(3) . . ?
C00U C012 C00R 107.44(3) . . ?
H012 C012 C00R 125.3(3) . . ?
H012 C012 C00U 127.2(3) . . ?
C00T C013 O004 126.01(4) . . ?
H013 C013 O004 122.3(3) . . ?
H013 C013 C00T 111.7(3) . . ?
C011 C014 C00X 119.92(4) . . ?
H014 C014 C00X 119.9(3) . . ?
H014 C014 C011 120.2(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C00C N005 C007 -17.43(4) . . . . ?
O001 C00C N005 C00E 179.85(3) . . . . ?
O001 C00C C00R C012 -0.62(3) . . . . ?
O001 C00U C00W O003 5.27(4) . . . . ?
O001 C00U C012 C00R 0.18(3) . . . . ?
O002 C00I N006 C00D -17.22(4) . . . . ?
O002 C00I N006 C00L 170.27(3) . . . . ?
O002 C00I C00Y C00Q 0.03(3) . . . . ?
O002 C00T C00Q C00Y 0.23(3) . . . . ?
O002 C00T C013 O004 1.48(4) . . . . ?
O003 C00W C00U C012 -174.03(4) . . . . ?
O004 C013 C00T C00Q 178.32(4) . . . . ?
N005 C007 C009 C00L 178.21(3) . . . . ?
N005 C007 C00A C00B -175.38(3) . . . . ?
N005 C007 C00A C00K 6.33(3) . . . . ?
N005 C00C C00R C012 -179.70(4) . . . . ?
N005 C00E C008 C00J 174.95(3) . . . . ?
N005 C00E C008 C00K -5.61(3) . . . . ?
N005 C00E C00M C00P -176.61(3) . . . . ?
N006 C00D C00G C00N 4.56(4) . . . . ?
N006 C00D C00G C00X -177.95(3) . . . . ?
N006 C00D C00O C011 178.62(3) . . . . ?
N006 C00I C00Y C00Q -179.52(5) . . . . ?
N006 C00L C009 C007 -178.48(3) . . . . ?
N006 C00L C00F C00B 175.93(3) . . . . ?
N006 C00L C00F C00N -5.62(4) . . . . ?
C007 C009 C00L C00F -3.33(4) . . . . ?
C007 C00A C00B C00F -2.81(4) . . . . ?
C007 C00A C00K C008 -43.54(3) . . . . ?
C007 C00A C00K C00S -167.20(3) . . . . ?
C007 C00A C00K C00V 73.56(3) . . . . ?
C008 C00E C00M C00P -0.29(4) . . . . ?
C008 C00J C00H C00P -0.34(4) . . . . ?
C008 C00K C00A C00B 138.28(3) . . . . ?
C009 C00L C00F C00B 0.70(4) . . . . ?
C009 C00L C00F C00N 179.15(3) . . . . ?
C00A C00B C00F C00L 2.44(4) . . . . ?
C00A C00B C00F C00N -175.92(3) . . . . ?
C00B C00F C00N C00G -141.92(3) . . . . ?
C00B C00F C00N C00Z -18.53(4) . . . . ?
C00B C00F C00N C010 101.18(4) . . . . ?
C00C C00R C012 C00U 0.26(3) . . . . ?
C00D C00G C00N C00F -39.25(3) . . . . ?
C00D C00G C00N C00Z -162.37(3) . . . . ?
C00D C00G C00N C010 78.31(3) . . . . ?
C00D C00G C00X C014 -0.28(4) . . . . ?
C00D C00O C011 C014 -1.36(4) . . . . ?
C00E C00M C00P C00H 1.76(4) . . . . ?
C00F C00N C00G C00X 143.38(3) . . . . ?
C00G C00X C014 C011 1.40(5) . . . . ?
C00I C00Y C00Q C00T -0.16(4) . . . . ?
C00O C011 C014 C00X -0.56(5) . . . . ?
C00R C012 C00U C00W 179.53(3) . . . . ?


_olex2_exptl_crystal_mounting_method 
'mounting on a cryo-loop using paratone oil'
_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_MJP_KD_AD00144_monomer_0m
_database_code_depnum_ccdc_archive 'CCDC 2373300'
loop_
_audit_author_name
_audit_author_address
'Milosz Pawlicki'
;Faculty of Chemistry, Jagiellonian University
Poland
;
_audit_update_record             
;
2024-07-24 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_audit_creation_date             2024-04-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
loop_
_audit_author_email
''
krzysztof.dzieszkowski@uj.edu.pl
_chemical_formula_moiety         'C34 H30 N2 O2'
_chemical_formula_sum            'C34 H30 N2 O2'
_chemical_formula_weight         498.629
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   9.7988(3)
_cell_length_b                   22.1962(7)
_cell_length_c                   23.7615(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5168.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      2.69
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0705 before and 0.0581 after correction.
The Ratio of minimum to maximum transmission is 0.9358.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       prism
_exptl_crystal_F_000             2113.227
_exptl_crystal_recrystallization_method 
'slow evaporation from DCM/hexane mixture'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.9974
_diffrn_reflns_Laue_measured_fraction_max 0.9883
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            71596
_diffrn_reflns_point_group_measured_fraction_full 0.9974
_diffrn_reflns_point_group_measured_fraction_max 0.9883
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.43
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_measured_fraction_theta_max 0.9883
_diffrn_measurement_device_type  'D8Quest Eco Photon50'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              0
_reflns_limit_k_max              29
_reflns_limit_k_min              0
_reflns_limit_l_max              31
_reflns_limit_l_min              0
_reflns_number_gt                5598
_reflns_number_total             6340
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.5245
_refine_diff_density_min         -0.4949
_refine_diff_density_rms         0.1147
_refine_ls_d_res_high            0.7500
_refine_ls_d_res_low             8.3872
_refine_ls_goodness_of_fit_ref   1.0503
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    57
_refine_ls_number_parameters     366
_refine_ls_number_reflns         6340
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0839
_refine_ls_restrained_S_all      1.0495
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0273P)²+15.2125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1573
_refine_ls_wR_factor_ref         0.1628
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C21-C1 \\sim C3-C2A
 with sigma of 0.02
 C21-C1A \\sim C3-C2
 with sigma of 0.02
 C2-C1 \\sim C2A-C1A
 with sigma of 0.02
 C21-C2 \\sim C3-C1A
 with sigma of 0.04
 C21-C2A \\sim C3-C1
 with sigma of 0.04
3. Others
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C2)=Sof(H2A)=Sof(H2B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C2A(H2AA,H2AB), C1A(H1AA,H1AB)
4.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C101(H101), C161(H161), C172(H172), C71(H71), C19(H19), C81(H81),
 C171(H171), C162(H162), C72(H72), C82(H82), C20(H20), C5(H5), C4(H4)
4.c Idealised Me refined as rotating group:
 C151(H15A,H15B,H15C), C152(H15D,H15E,H15F), C91(H91A,H91B,H91C), C92(H92A,
 H92B,H92C)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
O2 O 0.84640(17) 0.16693(7) 0.68022(7) 0.0165(3) Uani 1.000000 . . .
N2 N 0.72319(19) 0.16604(8) 0.59453(8) 0.0125(4) Uani 1.000000 . . .
N1 N 0.7822(2) 0.37411(9) 0.65000(8) 0.0153(4) Uani 1.000000 . . .
O1 O 0.8809(2) 0.31136(8) 0.71885(7) 0.0269(4) Uani 1.000000 . . .
C17 C 0.6210(2) 0.12067(10) 0.59692(9) 0.0132(4) Uani 1.000000 . . .
C12 C 0.7573(2) 0.27202(10) 0.61483(9) 0.0117(4) Uani 1.000000 . . .
H12 H 0.8455(2) 0.26270(10) 0.62888(9) 0.0140(5) Uiso 1.000000 R . .
C13 C 0.6780(2) 0.22701(10) 0.59127(9) 0.0102(4) Uani 1.000000 . . .
C10 C 0.5846(2) 0.34630(10) 0.59272(9) 0.0143(4) Uani 1.000000 . . .
C16 C 0.4930(2) 0.13207(10) 0.57220(9) 0.0143(4) Uani 1.000000 . . .
C11 C 0.7088(2) 0.33062(10) 0.61809(9) 0.0132(4) Uani 1.000000 . . .
C7 C 0.7038(2) 0.42103(10) 0.67507(10) 0.0167(5) Uani 1.000000 . . .
C151 C 0.3202(2) 0.20612(11) 0.53252(10) 0.0178(5) Uani 1.000000 . . .
H15A H 0.2721(4) 0.1731(4) 0.5137(7) 0.0268(7) Uiso 1.000000 GR . .
H15B H 0.2808(5) 0.2126(8) 0.56993(11) 0.0268(7) Uiso 1.000000 GR . .
H15C H 0.3110(3) 0.2430(5) 0.5102(6) 0.0268(7) Uiso 1.000000 GR . .
C8 C 0.5841(2) 0.43999(10) 0.64842(10) 0.0173(5) Uani 1.000000 . . .
C14 C 0.5517(2) 0.24027(10) 0.56715(9) 0.0111(4) Uani 1.000000 . . .
C18 C 0.8472(2) 0.15697(9) 0.62285(9) 0.0119(4) Uani 1.000000 . . .
C152 C 0.5316(3) 0.17936(11) 0.47889(9) 0.0186(5) Uani 1.000000 . . .
H15D H 0.6278(6) 0.1678(8) 0.48211(10) 0.0279(7) Uiso 1.000000 GR . .
H15E H 0.4807(12) 0.1471(6) 0.4602(3) 0.0279(7) Uiso 1.000000 GR . .
H15F H 0.5242(17) 0.2165(3) 0.4568(3) 0.0279(7) Uiso 1.000000 GR . .
C101 C 0.5093(2) 0.30050(10) 0.56772(9) 0.0137(4) Uani 1.000000 . . .
H101 H 0.4252(2) 0.31052(10) 0.55019(9) 0.0165(5) Uiso 1.000000 R . .
C9 C 0.5463(2) 0.41328(10) 0.59132(10) 0.0165(5) Uani 1.000000 . . .
C21 C 0.9809(3) 0.16575(11) 0.69717(12) 0.0250(6) Uani 1.000000 D . .
C15 C 0.4717(2) 0.19001(10) 0.53841(9) 0.0129(4) Uani 1.000000 . . .
C161 C 0.3937(3) 0.08761(12) 0.57605(11) 0.0221(5) Uani 1.000000 . . .
H161 H 0.3061(3) 0.09480(12) 0.56029(11) 0.0266(6) Uiso 1.000000 R . .
C172 C 0.5463(3) 0.02235(11) 0.62566(12) 0.0258(6) Uani 1.000000 . . .
H172 H 0.5644(3) -0.01519(11) 0.64335(12) 0.0310(7) Uiso 1.000000 R . .
C71 C 0.7477(3) 0.44740(11) 0.72509(10) 0.0209(5) Uani 1.000000 . . .
H71 H 0.8295(3) 0.43404(11) 0.74258(10) 0.0251(6) Uiso 1.000000 R . .
C19 C 0.9755(2) 0.14828(11) 0.60450(11) 0.0187(5) Uani 1.000000 . . .
H19 H 1.0036(2) 0.14012(11) 0.56700(11) 0.0224(6) Uiso 1.000000 R . .
C6 C 0.9004(3) 0.35340(10) 0.67705(10) 0.0178(5) Uani 1.000000 . . .
C91 C 0.3952(3) 0.42251(12) 0.57667(12) 0.0238(6) Uani 1.000000 . . .
H91A H 0.3755(5) 0.4038(7) 0.5402(4) 0.0357(8) Uiso 1.000000 GR . .
H91B H 0.3382(3) 0.4039(8) 0.6058(4) 0.0357(8) Uiso 1.000000 GR . .
H91C H 0.3754(5) 0.46573(12) 0.5746(8) 0.0357(8) Uiso 1.000000 GR . .
C81 C 0.5095(3) 0.48615(11) 0.67405(11) 0.0226(5) Uani 1.000000 . . .
H81 H 0.4277(3) 0.49991(11) 0.65680(11) 0.0271(6) Uiso 1.000000 R . .
C92 C 0.6335(3) 0.44505(11) 0.54595(10) 0.0202(5) Uani 1.000000 . . .
H92A H 0.7305(3) 0.4381(7) 0.5537(4) 0.0304(8) Uiso 1.000000 GR . .
H92B H 0.6106(14) 0.4288(6) 0.50880(13) 0.0304(8) Uiso 1.000000 GR . .
H92C H 0.6147(14) 0.48842(15) 0.5466(5) 0.0304(8) Uiso 1.000000 GR . .
C171 C 0.6469(2) 0.06584(11) 0.62341(10) 0.0181(5) Uani 1.000000 . . .
H171 H 0.7336(2) 0.05839(11) 0.63989(10) 0.0217(6) Uiso 1.000000 R . .
C162 C 0.4192(3) 0.03312(12) 0.60229(12) 0.0267(6) Uani 1.000000 . . .
H162 H 0.3499(3) 0.00326(12) 0.60425(12) 0.0320(7) Uiso 1.000000 R . .
C72 C 0.6716(3) 0.49316(11) 0.74915(12) 0.0258(6) Uani 1.000000 . . .
H72 H 0.7017(3) 0.51151(11) 0.78307(12) 0.0310(7) Uiso 1.000000 R . .
C82 C 0.5520(3) 0.51229(11) 0.72412(12) 0.0263(6) Uani 1.000000 . . .
H82 H 0.4991(3) 0.54322(11) 0.74110(12) 0.0315(7) Uiso 1.000000 R . .
C20 C 1.0612(3) 0.15388(12) 0.65320(13) 0.0271(6) Uani 1.000000 . . .
H20 H 1.1578(3) 0.14987(12) 0.65398(13) 0.0325(7) Uiso 1.000000 R . .
C5 C 1.0338(3) 0.36084(12) 0.66652(13) 0.0275(6) Uani 1.000000 . . .
H5 H 1.0736(3) 0.38747(12) 0.63987(13) 0.0330(7) Uiso 1.000000 R . .
C1 C 0.9752(12) 0.1876(5) 0.7625(4) 0.023(2) Uani 0.439(15) D P 1
H1A H 0.8788(12) 0.1934(5) 0.7738(4) 0.027(2) Uiso 0.439(15) R P 1
H1B H 1.0146(12) 0.1558(5) 0.7868(4) 0.027(2) Uiso 0.439(15) R P 1
C3 C 1.0084(4) 0.29129(13) 0.73343(13) 0.0433(10) Uani 1.000000 D . .
C4 C 1.1035(4) 0.32086(15) 0.70324(17) 0.0478(10) Uani 1.000000 . . .
H4 H 1.1995(4) 0.31589(15) 0.70601(17) 0.0573(12) Uiso 1.000000 R . .
C2 C 1.0537(11) 0.2467(3) 0.7719(3) 0.020(2) Uani 0.439(15) D P 1
H2A H 1.0391(11) 0.2609(3) 0.8109(3) 0.024(2) Uiso 0.439(15) R P 1
H2B H 1.1526(11) 0.2396(3) 0.7666(3) 0.024(2) Uiso 0.439(15) R P 1
C2A C 0.9780(9) 0.2371(2) 0.7778(2) 0.0240(18) Uani 0.561(15) D P 2
H2AA H 1.0250(9) 0.2456(2) 0.8138(2) 0.029(2) Uiso 0.561(15) R P 2
H2AB H 0.8788(9) 0.2349(2) 0.7853(2) 0.029(2) Uiso 0.561(15) R P 2
C1A C 1.0280(9) 0.1760(3) 0.7541(3) 0.0198(14) Uani 0.561(15) D P 2
H1AA H 0.9948(9) 0.1431(3) 0.7786(3) 0.0238(17) Uiso 0.561(15) R P 2
H1AB H 1.1290(9) 0.1752(3) 0.7547(3) 0.0238(17) Uiso 0.561(15) R P 2


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
O2 C18 1.381(3) . ?
O2 C21 1.378(3) . ?
N2 C17 1.421(3) . ?
N2 C13 1.426(3) . ?
N2 C18 1.404(3) . ?
N1 C11 1.422(3) . ?
N1 C7 1.425(3) . ?
N1 C6 1.402(3) . ?
O1 C6 1.376(3) . ?
O1 C3 1.371(4) . ?
C17 C16 1.408(3) . ?
C17 C171 1.393(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(3) . ?
C12 C11 1.387(3) . ?
C13 C14 1.396(3) . ?
C10 C11 1.402(3) . ?
C10 C101 1.390(3) . ?
C10 C9 1.534(3) . ?
C16 C15 1.531(3) . ?
C16 C161 1.389(3) . ?
C7 C8 1.398(3) . ?
C7 C71 1.393(3) . ?
C151 H15A 0.9800 . ?
C151 H15B 0.9800 . ?
C151 H15C 0.9800 . ?
C151 C15 1.533(3) . ?
C8 C9 1.526(3) . ?
C8 C81 1.399(3) . ?
C14 C101 1.400(3) . ?
C14 C15 1.525(3) . ?
C18 C19 1.344(3) . ?
C152 H15D 0.9800 . ?
C152 H15E 0.9800 . ?
C152 H15F 0.9800 . ?
C152 C15 1.550(3) . ?
C101 H101 0.9500 . ?
C9 C91 1.535(3) . ?
C9 C92 1.546(3) . ?
C21 C20 1.335(4) . ?
C21 C1 1.628(10) . ?
C21 C1A 1.448(7) . ?
C161 H161 0.9500 . ?
C161 C162 1.384(4) . ?
C172 H172 0.9500 . ?
C172 C171 1.381(3) . ?
C172 C162 1.384(4) . ?
C71 H71 0.9500 . ?
C71 C72 1.384(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.436(4) . ?
C6 C5 1.340(4) . ?
C91 H91A 0.9800 . ?
C91 H91B 0.9800 . ?
C91 H91C 0.9800 . ?
C81 H81 0.9500 . ?
C81 C82 1.388(4) . ?
C92 H92A 0.9800 . ?
C92 H92B 0.9800 . ?
C92 H92C 0.9800 . ?
C171 H171 0.9500 . ?
C162 H162 0.9500 . ?
C72 H72 0.9500 . ?
C72 C82 1.381(4) . ?
C82 H82 0.9500 . ?
C20 H20 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.419(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.536(11) . ?
C3 C4 1.347(6) . ?
C3 C2 1.419(6) . ?
C3 C2A 1.627(7) . ?
C4 H4 0.9500 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C1A 1.547(9) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O2 C18 106.26(19) . . ?
C13 N2 C17 117.13(18) . . ?
C18 N2 C17 119.29(18) . . ?
C18 N2 C13 115.53(18) . . ?
C7 N1 C11 116.53(19) . . ?
C6 N1 C11 116.06(19) . . ?
C6 N1 C7 119.56(19) . . ?
C3 O1 C6 106.0(2) . . ?
C16 C17 N2 118.9(2) . . ?
C171 C17 N2 120.6(2) . . ?
C171 C17 C16 120.5(2) . . ?
C13 C12 H12 119.74(13) . . ?
C11 C12 H12 119.74(13) . . ?
C11 C12 C13 120.5(2) . . ?
C12 C13 N2 119.27(19) . . ?
C14 C13 N2 119.85(19) . . ?
C14 C13 C12 120.8(2) . . ?
C101 C10 C11 117.6(2) . . ?
C9 C10 C11 117.5(2) . . ?
C9 C10 C101 124.8(2) . . ?
C15 C16 C17 119.5(2) . . ?
C161 C16 C17 118.0(2) . . ?
C161 C16 C15 122.4(2) . . ?
C12 C11 N1 119.6(2) . . ?
C10 C11 N1 120.0(2) . . ?
C10 C11 C12 120.4(2) . . ?
C8 C7 N1 118.9(2) . . ?
C71 C7 N1 119.8(2) . . ?
C71 C7 C8 121.3(2) . . ?
H15B C151 H15A 109.5 . . ?
H15C C151 H15A 109.5 . . ?
H15C C151 H15B 109.5 . . ?
C15 C151 H15A 109.5 . . ?
C15 C151 H15B 109.5 . . ?
C15 C151 H15C 109.5 . . ?
C9 C8 C7 119.3(2) . . ?
C81 C8 C7 117.5(2) . . ?
C81 C8 C9 123.0(2) . . ?
C101 C14 C13 117.4(2) . . ?
C15 C14 C13 119.06(19) . . ?
C15 C14 C101 123.4(2) . . ?
N2 C18 O2 116.45(19) . . ?
C19 C18 O2 110.4(2) . . ?
C19 C18 N2 132.4(2) . . ?
H15E C152 H15D 109.5 . . ?
H15F C152 H15D 109.5 . . ?
H15F C152 H15E 109.5 . . ?
C15 C152 H15D 109.5 . . ?
C15 C152 H15E 109.5 . . ?
C15 C152 H15F 109.5 . . ?
C14 C101 C10 123.1(2) . . ?
H101 C101 C10 118.46(13) . . ?
H101 C101 C14 118.46(13) . . ?
C8 C9 C10 107.33(19) . . ?
C91 C9 C10 111.7(2) . . ?
C91 C9 C8 112.6(2) . . ?
C92 C9 C10 108.80(19) . . ?
C92 C9 C8 107.98(19) . . ?
C92 C9 C91 108.3(2) . . ?
C20 C21 O2 109.8(2) . . ?
C1 C21 O2 103.9(5) . . ?
C1 C21 C20 145.7(5) . . ?
C1A C21 O2 125.1(4) . . ?
C1A C21 C20 125.1(4) . . ?
C1A C21 C1 22.0(3) . . ?
C151 C15 C16 112.10(19) . . ?
C14 C15 C16 108.03(17) . . ?
C14 C15 C151 111.59(19) . . ?
C152 C15 C16 107.38(19) . . ?
C152 C15 C151 108.60(18) . . ?
C152 C15 C14 109.00(18) . . ?
H161 C161 C16 119.21(14) . . ?
C162 C161 C16 121.6(2) . . ?
C162 C161 H161 119.21(15) . . ?
C171 C172 H172 119.80(15) . . ?
C162 C172 H172 119.80(15) . . ?
C162 C172 C171 120.4(2) . . ?
H71 C71 C7 120.18(15) . . ?
C72 C71 C7 119.6(3) . . ?
C72 C71 H71 120.18(17) . . ?
H19 C19 C18 127.06(14) . . ?
C20 C19 C18 105.9(2) . . ?
C20 C19 H19 127.06(15) . . ?
O1 C6 N1 116.0(2) . . ?
C5 C6 N1 132.8(2) . . ?
C5 C6 O1 110.7(2) . . ?
H91A C91 C9 109.5 . . ?
H91B C91 C9 109.5 . . ?
H91B C91 H91A 109.5 . . ?
H91C C91 C9 109.5 . . ?
H91C C91 H91A 109.5 . . ?
H91C C91 H91B 109.5 . . ?
H81 C81 C8 119.25(16) . . ?
C82 C81 C8 121.5(3) . . ?
C82 C81 H81 119.25(16) . . ?
H92A C92 C9 109.5 . . ?
H92B C92 C9 109.5 . . ?
H92B C92 H92A 109.5 . . ?
H92C C92 C9 109.5 . . ?
H92C C92 H92A 109.5 . . ?
H92C C92 H92B 109.5 . . ?
C172 C171 C17 119.9(2) . . ?
H171 C171 C17 120.06(14) . . ?
H171 C171 C172 120.06(15) . . ?
C172 C162 C161 119.6(2) . . ?
H162 C162 C161 120.18(15) . . ?
H162 C162 C172 120.18(15) . . ?
H72 C72 C71 119.83(17) . . ?
C82 C72 C71 120.3(3) . . ?
C82 C72 H72 119.83(15) . . ?
C72 C82 C81 119.7(2) . . ?
H82 C82 C81 120.15(16) . . ?
H82 C82 C72 120.15(15) . . ?
C19 C20 C21 107.6(2) . . ?
H20 C20 C21 126.19(15) . . ?
H20 C20 C19 126.19(15) . . ?
H5 C5 C6 126.95(17) . . ?
C4 C5 C6 106.1(3) . . ?
C4 C5 H5 126.9(2) . . ?
H1A C1 C21 109.2(4) . . ?
H1B C1 C21 109.2(4) . . ?
H1B C1 H1A 107.9 . . ?
C2 C1 C21 112.1(7) . . ?
C2 C1 H1A 109.2(7) . . ?
C2 C1 H1B 109.2(5) . . ?
C4 C3 O1 109.7(3) . . ?
C2 C3 O1 132.4(6) . . ?
C2 C3 C4 117.8(5) . . ?
C2A C3 O1 103.7(4) . . ?
C2A C3 C4 146.3(4) . . ?
C2A C3 C2 28.8(3) . . ?
C3 C4 C5 107.4(3) . . ?
H4 C4 C5 126.3(2) . . ?
H4 C4 C3 126.30(18) . . ?
C3 C2 C1 110.2(7) . . ?
H2A C2 C1 109.6(5) . . ?
H2A C2 C3 109.6(3) . . ?
H2B C2 C1 109.6(7) . . ?
H2B C2 C3 109.6(5) . . ?
H2B C2 H2A 108.1 . . ?
H2AA C2A C3 109.5(2) . . ?
H2AB C2A C3 109.5(3) . . ?
H2AB C2A H2AA 108.1 . . ?
C1A C2A C3 110.7(6) . . ?
C1A C2A H2AA 109.5(3) . . ?
C1A C2A H2AB 109.5(6) . . ?
C2A C1A C21 112.1(5) . . ?
H1AA C1A C21 109.2(3) . . ?
H1AA C1A C2A 109.2(5) . . ?
H1AB C1A C21 109.2(4) . . ?
H1AB C1A C2A 109.2(6) . . ?
H1AB C1A H1AA 107.9 . . ?

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
O2 C18 N2 C17 -79.1(2) . . . . ?
O2 C18 N2 C13 68.8(2) . . . . ?
O2 C18 C19 C20 -0.8(2) . . . . ?
O2 C21 C20 C19 1.3(2) . . . . ?
O2 C21 C1 C2 -117.5(6) . . . . ?
O2 C21 C1A C2A -55.4(6) . . . . ?
N2 C17 C16 C15 6.1(2) . . . . ?
N2 C17 C16 C161 -178.7(2) . . . . ?
N2 C17 C171 C172 179.6(2) . . . . ?
N2 C13 C12 C11 -172.50(19) . . . . ?
N2 C13 C14 C101 176.73(19) . . . . ?
N2 C13 C14 C15 -7.2(2) . . . . ?
N2 C18 C19 C20 168.7(3) . . . . ?
N1 C11 C12 C13 170.35(19) . . . . ?
N1 C11 C10 C101 -172.6(2) . . . . ?
N1 C11 C10 C9 11.2(2) . . . . ?
N1 C7 C8 C9 -4.4(2) . . . . ?
N1 C7 C8 C81 -180.0(2) . . . . ?
N1 C7 C71 C72 179.7(2) . . . . ?
N1 C6 O1 C3 171.4(2) . . . . ?
N1 C6 C5 C4 -170.7(3) . . . . ?
O1 C6 C5 C4 0.6(2) . . . . ?
O1 C3 C4 C5 -1.4(2) . . . . ?
O1 C3 C2 C1 49.6(7) . . . . ?
O1 C3 C2A C1A 115.9(5) . . . . ?
C17 C16 C15 C151 -159.9(2) . . . . ?
C17 C16 C15 C14 -36.5(2) . . . . ?
C17 C16 C15 C152 80.9(2) . . . . ?
C17 C16 C161 C162 -1.3(3) . . . . ?
C17 C171 C172 C162 -0.7(3) . . . . ?
C12 C13 C14 C101 0.2(2) . . . . ?
C12 C13 C14 C15 176.22(19) . . . . ?
C12 C11 C10 C101 4.0(2) . . . . ?
C12 C11 C10 C9 -172.2(2) . . . . ?
C13 C14 C101 C10 -2.4(2) . . . . ?
C13 C14 C15 C16 37.0(2) . . . . ?
C13 C14 C15 C151 160.6(2) . . . . ?
C13 C14 C15 C152 -79.4(2) . . . . ?
C10 C101 C14 C15 -178.2(2) . . . . ?
C10 C9 C8 C7 38.4(2) . . . . ?
C10 C9 C8 C81 -146.33(19) . . . . ?
C16 C15 C14 C101 -147.25(18) . . . . ?
C16 C161 C162 C172 0.4(3) . . . . ?
C7 C8 C9 C91 161.7(2) . . . . ?
C7 C8 C9 C92 -78.8(2) . . . . ?
C7 C8 C81 C82 -0.1(3) . . . . ?
C7 C71 C72 C82 0.6(3) . . . . ?
C151 C15 C14 C101 -23.6(2) . . . . ?
C8 C81 C82 C72 0.9(3) . . . . ?
C18 C19 C20 C21 -0.3(2) . . . . ?
C21 C1 C2 C3 52.8(8) . . . . ?
C21 C1A C2A C3 -49.4(6) . . . . ?
C161 C162 C172 C171 0.6(3) . . . . ?
C71 C72 C82 C81 -1.1(3) . . . . ?
C6 C5 C4 C3 0.5(3) . . . . ?
C5 C4 C3 C2 177.6(3) . . . . ?
C5 C4 C3 C2A 171.5(3) . . . . ?
C1 C2 C3 C4 -129.1(9) . . . . ?
C1 C2 C3 C2A 43.9(10) . . . . ?


_olex2_date_sample_completion    2023-06-02
_olex2_date_sample_data_collection 2023-06-01
_olex2_date_sample_submission    2023-06-01
_olex2_exptl_crystal_mounting_method 
'mounting on a cryo-loop using paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'
_radiation_monochromator         Triumph
loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
C21 C1 1 1
C21 C2 1 4
C21 C2A 1 5
C21 C1A 1 2
C3 C1 1 5
C3 C2 1 2
C3 C2A 1 1
C3 C1A 1 4
C2 C1 1 3
C2A C1A 1 3

loop_
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
_restr_equal_distance_class_average
_restr_equal_distance_class_esd
_restr_equal_distance_class_diff_max
1 0.0200 1.6276 0.0003 0.0003
2 0.0200 1.4334 0.0144 0.0144
3 0.0200 1.5416 0.0055 0.0055
4 0.0400 2.6185 0.0060 0.0060
5 0.0400 2.4550 0.0304 0.0304

