# Electronic Supplementary Material (ESI) for Inorganic 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_210513b_a
_database_code_depnum_ccdc_archive 'CCDC 2205391'
loop_
_audit_author_name
_audit_author_address
'Yanhong Liu'
;Tongji University
China
;
_audit_update_record             
;
2022-09-05 deposited with the CCDC.	2023-12-27 downloaded from the CCDC.
;
_audit_creation_method           
;
FinalCif V85 by Daniel Kratzert, Freiburg 2021,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C41 H30 N4 O4'
_chemical_formula_moiety         ?
_chemical_formula_weight         642.69
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   22.5474(12)
_cell_length_b                   12.5664(8)
_cell_length_c                   22.7995(14)
_cell_angle_alpha                90
_cell_angle_beta                 100.306(2)
_cell_angle_gamma                90
_cell_volume                     6355.8(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      2.714
_cell_measurement_theta_max      25.352
_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6972
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.996
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            53862
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_theta_min         2.714
_diffrn_reflns_theta_max         25.376
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5844
_reflns_number_gt                4345
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40A'
_computing_data_reduction        'SAINT V8.40A'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0341P)²+5.7521P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5844
_refine_ls_number_parameters     443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00052(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

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'

_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_
_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 0.58527(7) -0.00175(11) 0.72260(6) 0.0359(4) Uani 1 1 d . . . . .
O2 O 0.57755(7) -0.58793(11) 0.72682(7) 0.0408(4) Uani 1 1 d . . . . .
O3 O 0.53513(6) -0.06164(10) 0.63533(6) 0.0310(3) Uani 1 1 d . . . . .
H3A H 0.531939 0.003624 0.627428 0.046 Uiso 1 1 calc R U . . .
O4 O 0.64055(6) -0.52866(10) 0.80715(5) 0.0279(3) Uani 1 1 d . . . . .
H4A H 0.641895 -0.593212 0.816868 0.042 Uiso 1 1 calc R U . . .
N1 N 0.51380(7) 0.13127(12) 0.59817(7) 0.0264(4) Uani 1 1 d . . . . .
N2 N 0.34470(6) 0.70275(11) 0.45431(6) 0.0198(3) Uani 1 1 d . . . . .
N3 N 0.16988(7) 0.70890(14) 0.08970(7) 0.0290(4) Uani 1 1 d . . . . .
N4 N 0.34938(6) 1.28117(12) 0.64863(7) 0.0232(4) Uani 1 1 d . . . . .
C1 C 0.46145(7) 0.32285(14) 0.55228(8) 0.0186(4) Uani 1 1 d . . . . .
C2 C 0.45807(8) 0.23128(14) 0.51733(8) 0.0213(4) Uani 1 1 d . . . . .
H2 H 0.437911 0.232723 0.477009 0.026 Uiso 1 1 calc R U . . .
C3 C 0.48423(8) 0.13880(15) 0.54185(9) 0.0254(4) Uani 1 1 d . . . . .
H3 H 0.481159 0.076937 0.517540 0.031 Uiso 1 1 calc R U . . .
C4 C 0.51722(8) 0.21878(15) 0.63179(9) 0.0256(4) Uani 1 1 d . . . . .
H4 H 0.537933 0.214747 0.671853 0.031 Uiso 1 1 calc R U . . .
C5 C 0.49207(8) 0.31496(15) 0.61110(8) 0.0226(4) Uani 1 1 d . . . . .
H5 H 0.495563 0.375231 0.636636 0.027 Uiso 1 1 calc R U . . .
C6 C 0.43286(7) 0.42299(14) 0.52768(8) 0.0180(4) Uani 1 1 d . . . . .
C7 C 0.40736(7) 0.49379(14) 0.56314(8) 0.0197(4) Uani 1 1 d . . . . .
H7 H 0.410213 0.479267 0.604446 0.024 Uiso 1 1 calc R U . . .
C8 C 0.37799(8) 0.58476(14) 0.53935(8) 0.0200(4) Uani 1 1 d . . . . .
H8 H 0.359817 0.630637 0.564138 0.024 Uiso 1 1 calc R U . . .
C9 C 0.37478(7) 0.60988(14) 0.47907(8) 0.0183(4) Uani 1 1 d . . . . .
C10 C 0.40143(7) 0.54094(14) 0.44373(8) 0.0185(4) Uani 1 1 d . . . . .
H10 H 0.400495 0.557275 0.402896 0.022 Uiso 1 1 calc R U . . .
C11 C 0.42923(7) 0.44887(14) 0.46765(8) 0.0184(4) Uani 1 1 d . . . . .
H11 H 0.446338 0.401940 0.442570 0.022 Uiso 1 1 calc R U . . .
C12 C 0.31650(7) 0.70294(14) 0.39308(8) 0.0186(4) Uani 1 1 d . . . . .
C13 C 0.27897(8) 0.61937(14) 0.36968(8) 0.0202(4) Uani 1 1 d . . . . .
H13 H 0.271983 0.561875 0.394633 0.024 Uiso 1 1 calc R U . . .
C14 C 0.25189(8) 0.61983(14) 0.31033(8) 0.0203(4) Uani 1 1 d . . . . .
H14 H 0.226969 0.561750 0.294800 0.024 Uiso 1 1 calc R U . . .
C15 C 0.26042(7) 0.70398(14) 0.27271(8) 0.0189(4) Uani 1 1 d . . . . .
C16 C 0.29800(8) 0.78748(14) 0.29699(8) 0.0188(4) Uani 1 1 d . . . . .
H16 H 0.304328 0.845794 0.272314 0.023 Uiso 1 1 calc R U . . .
C17 C 0.32610(8) 0.78704(14) 0.35598(8) 0.0193(4) Uani 1 1 d . . . . .
H17 H 0.351985 0.844025 0.371301 0.023 Uiso 1 1 calc R U . . .
C18 C 0.34374(8) 0.79674(14) 0.48838(8) 0.0188(4) Uani 1 1 d . . . . .
C19 C 0.29368(8) 0.86424(14) 0.47773(8) 0.0194(4) Uani 1 1 d . . . . .
H19 H 0.259658 0.845692 0.448569 0.023 Uiso 1 1 calc R U . . .
C20 C 0.29354(8) 0.95786(14) 0.50949(7) 0.0189(4) Uani 1 1 d . . . . .
H20 H 0.259661 1.003868 0.500999 0.023 Uiso 1 1 calc R U . . .
C21 C 0.34213(8) 0.98643(14) 0.55386(7) 0.0190(4) Uani 1 1 d . . . . .
C22 C 0.39120(8) 0.91682(14) 0.56497(8) 0.0206(4) Uani 1 1 d . . . . .
H22 H 0.424333 0.933343 0.595612 0.025 Uiso 1 1 calc R U . . .
C23 C 0.39254(8) 0.82461(14) 0.53238(8) 0.0205(4) Uani 1 1 d . . . . .
H23 H 0.426980 0.779752 0.539968 0.025 Uiso 1 1 calc R U . . .
C24 C 0.22974(7) 0.70502(14) 0.20953(8) 0.0194(4) Uani 1 1 d . . . . .
C25 C 0.21387(8) 0.80056(15) 0.17961(8) 0.0224(4) Uani 1 1 d . . . . .
H25 H 0.222737 0.866635 0.199489 0.027 Uiso 1 1 calc R U . . .
C26 C 0.18514(8) 0.79810(16) 0.12079(8) 0.0262(4) Uani 1 1 d . . . . .
H26 H 0.175570 0.864155 0.101100 0.031 Uiso 1 1 calc R U . . .
C27 C 0.18473(8) 0.61795(16) 0.11902(8) 0.0264(4) Uani 1 1 d . . . . .
H27 H 0.174019 0.553140 0.098375 0.032 Uiso 1 1 calc R U . . .
C28 C 0.21464(8) 0.61187(15) 0.17738(8) 0.0223(4) Uani 1 1 d . . . . .
H28 H 0.224803 0.544582 0.195393 0.027 Uiso 1 1 calc R U . . .
C29 C 0.34315(7) 1.08770(14) 0.58708(8) 0.0188(4) Uani 1 1 d . . . . .
C30 C 0.31724(8) 1.17991(14) 0.55984(8) 0.0204(4) Uani 1 1 d . . . . .
H30 H 0.296988 1.178428 0.519553 0.024 Uiso 1 1 calc R U . . .
C31 C 0.32130(8) 1.27353(15) 0.59204(8) 0.0222(4) Uani 1 1 d . . . . .
H31 H 0.303185 1.335666 0.572946 0.027 Uiso 1 1 calc R U . . .
C32 C 0.37437(8) 1.19288(15) 0.67505(8) 0.0240(4) Uani 1 1 d . . . . .
H32 H 0.394640 1.197231 0.715261 0.029 Uiso 1 1 calc R U . . .
C33 C 0.37201(8) 1.09592(15) 0.64652(8) 0.0225(4) Uani 1 1 d . . . . .
H33 H 0.389908 1.034962 0.667120 0.027 Uiso 1 1 calc R U . . .
C34 C 0.56379(8) -0.07454(15) 0.69050(8) 0.0241(4) Uani 1 1 d . . . . .
C35 C 0.56910(8) -0.18863(14) 0.70924(8) 0.0213(4) Uani 1 1 d . . . . .
C36 C 0.60279(8) -0.21459(15) 0.76440(8) 0.0221(4) Uani 1 1 d . . . . .
H36 H 0.618937 -0.159619 0.791161 0.026 Uiso 1 1 calc R U . . .
C37 C 0.61305(8) -0.31988(15) 0.78076(8) 0.0226(4) Uani 1 1 d . . . . .
H37 H 0.636970 -0.336881 0.818260 0.027 Uiso 1 1 calc R U . . .
C38 C 0.58849(8) -0.40083(14) 0.74254(8) 0.0208(4) Uani 1 1 d . . . . .
C39 C 0.55217(8) -0.37474(15) 0.68847(8) 0.0234(4) Uani 1 1 d . . . . .
H39 H 0.533640 -0.429646 0.662936 0.028 Uiso 1 1 calc R U . . .
C40 C 0.54290(8) -0.26978(15) 0.67169(8) 0.0239(4) Uani 1 1 d . . . . .
H40 H 0.518556 -0.252745 0.634415 0.029 Uiso 1 1 calc R U . . .
C41 C 0.60095(8) -0.51557(15) 0.75759(8) 0.0236(4) Uani 1 1 d . . . . .


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 C34 1.217(2) . ?
O2 C41 1.210(2) . ?
O3 C34 1.317(2) . ?
O3 H3A 0.8400 . ?
O4 C41 1.319(2) . ?
O4 H4A 0.8400 . ?
N1 C4 1.335(3) . ?
N1 C3 1.340(2) . ?
N2 C9 1.416(2) . ?
N2 C18 1.416(2) . ?
N2 C12 1.427(2) . ?
N3 C27 1.336(3) . ?
N3 C26 1.338(3) . ?
N4 C31 1.335(2) . ?
N4 C32 1.338(2) . ?
C1 C2 1.394(2) . ?
C1 C5 1.398(2) . ?
C1 C6 1.478(2) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.394(2) . ?
C6 C11 1.395(2) . ?
C7 C8 1.383(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.399(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(2) . ?
C10 C11 1.381(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.394(2) . ?
C12 C17 1.395(2) . ?
C13 C14 1.381(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.396(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.399(2) . ?
C15 C24 1.482(2) . ?
C16 C17 1.380(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.395(2) . ?
C18 C19 1.398(2) . ?
C19 C20 1.382(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.399(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.398(2) . ?
C21 C29 1.479(2) . ?
C22 C23 1.380(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C28 1.391(2) . ?
C24 C25 1.396(2) . ?
C25 C26 1.381(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.382(2) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.393(2) . ?
C29 C33 1.398(2) . ?
C30 C31 1.381(2) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C33 1.378(3) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C35 1.495(3) . ?
C35 C36 1.387(3) . ?
C35 C40 1.393(3) . ?
C36 C37 1.383(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.389(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.392(2) . ?
C38 C41 1.497(3) . ?
C39 C40 1.379(3) . ?
C39 H39 0.9500 . ?
C40 H40 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
C34 O3 H3A 109.5 . . ?
C41 O4 H4A 109.5 . . ?
C4 N1 C3 117.37(16) . . ?
C9 N2 C18 121.47(14) . . ?
C9 N2 C12 119.30(14) . . ?
C18 N2 C12 119.19(14) . . ?
C27 N3 C26 115.72(16) . . ?
C31 N4 C32 117.65(16) . . ?
C2 C1 C5 117.20(16) . . ?
C2 C1 C6 120.68(16) . . ?
C5 C1 C6 122.11(16) . . ?
C3 C2 C1 119.30(17) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
N1 C3 C2 123.54(18) . . ?
N1 C3 H3 118.2 . . ?
C2 C3 H3 118.2 . . ?
N1 C4 C5 123.14(18) . . ?
N1 C4 H4 118.4 . . ?
C5 C4 H4 118.4 . . ?
C4 C5 C1 119.45(18) . . ?
C4 C5 H5 120.3 . . ?
C1 C5 H5 120.3 . . ?
C7 C6 C11 117.55(16) . . ?
C7 C6 C1 121.36(16) . . ?
C11 C6 C1 121.07(16) . . ?
C8 C7 C6 121.24(16) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 120.59(16) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 118.47(16) . . ?
C10 C9 N2 120.56(15) . . ?
C8 C9 N2 120.97(16) . . ?
C11 C10 C9 120.39(16) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C6 121.72(16) . . ?
C10 C11 H11 119.1 . . ?
C6 C11 H11 119.1 . . ?
C13 C12 C17 119.23(16) . . ?
C13 C12 N2 120.47(16) . . ?
C17 C12 N2 120.30(16) . . ?
C14 C13 C12 120.24(17) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 121.30(17) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C16 117.72(16) . . ?
C14 C15 C24 120.79(16) . . ?
C16 C15 C24 121.48(16) . . ?
C17 C16 C15 121.49(17) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C12 120.01(16) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
C23 C18 C19 118.77(16) . . ?
C23 C18 N2 121.10(15) . . ?
C19 C18 N2 120.13(15) . . ?
C20 C19 C18 120.20(16) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 121.52(16) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C22 C21 C20 117.56(16) . . ?
C22 C21 C29 120.43(16) . . ?
C20 C21 C29 121.99(16) . . ?
C23 C22 C21 121.40(16) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C22 C23 C18 120.51(16) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
C28 C24 C25 116.69(16) . . ?
C28 C24 C15 122.18(16) . . ?
C25 C24 C15 121.13(16) . . ?
C26 C25 C24 119.35(18) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
N3 C26 C25 124.37(18) . . ?
N3 C26 H26 117.8 . . ?
C25 C26 H26 117.8 . . ?
N3 C27 C28 124.37(18) . . ?
N3 C27 H27 117.8 . . ?
C28 C27 H27 117.8 . . ?
C27 C28 C24 119.49(18) . . ?
C27 C28 H28 120.3 . . ?
C24 C28 H28 120.3 . . ?
C30 C29 C33 117.13(16) . . ?
C30 C29 C21 121.39(16) . . ?
C33 C29 C21 121.45(16) . . ?
C31 C30 C29 119.28(17) . . ?
C31 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?
N4 C31 C30 123.36(17) . . ?
N4 C31 H31 118.3 . . ?
C30 C31 H31 118.3 . . ?
N4 C32 C33 122.91(17) . . ?
N4 C32 H32 118.5 . . ?
C33 C32 H32 118.5 . . ?
C32 C33 C29 119.67(17) . . ?
C32 C33 H33 120.2 . . ?
C29 C33 H33 120.2 . . ?
O1 C34 O3 123.80(18) . . ?
O1 C34 C35 123.12(17) . . ?
O3 C34 C35 113.04(16) . . ?
C36 C35 C40 119.23(17) . . ?
C36 C35 C34 119.19(16) . . ?
C40 C35 C34 121.54(16) . . ?
C37 C36 C35 120.51(17) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C36 C37 C38 120.20(17) . . ?
C36 C37 H37 119.9 . . ?
C38 C37 H37 119.9 . . ?
C37 C38 C39 119.26(17) . . ?
C37 C38 C41 121.63(16) . . ?
C39 C38 C41 119.11(16) . . ?
C40 C39 C38 120.47(17) . . ?
C40 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C39 C40 C35 120.21(17) . . ?
C39 C40 H40 119.9 . . ?
C35 C40 H40 119.9 . . ?
O2 C41 O4 124.12(17) . . ?
O2 C41 C38 123.11(17) . . ?
O4 C41 C38 112.76(16) . . ?

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
C5 C1 C2 C3 0.3(3) . . . . ?
C6 C1 C2 C3 -178.85(16) . . . . ?
C4 N1 C3 C2 0.5(3) . . . . ?
C1 C2 C3 N1 -0.6(3) . . . . ?
C3 N1 C4 C5 -0.2(3) . . . . ?
N1 C4 C5 C1 -0.1(3) . . . . ?
C2 C1 C5 C4 0.0(3) . . . . ?
C6 C1 C5 C4 179.17(16) . . . . ?
C2 C1 C6 C7 145.75(17) . . . . ?
C5 C1 C6 C7 -33.4(2) . . . . ?
C2 C1 C6 C11 -32.8(2) . . . . ?
C5 C1 C6 C11 148.08(17) . . . . ?
C11 C6 C7 C8 1.9(2) . . . . ?
C1 C6 C7 C8 -176.71(16) . . . . ?
C6 C7 C8 C9 -2.0(3) . . . . ?
C7 C8 C9 C10 0.4(2) . . . . ?
C7 C8 C9 N2 179.88(16) . . . . ?
C18 N2 C9 C10 -147.98(16) . . . . ?
C12 N2 C9 C10 29.8(2) . . . . ?
C18 N2 C9 C8 32.6(2) . . . . ?
C12 N2 C9 C8 -149.65(16) . . . . ?
C8 C9 C10 C11 1.3(2) . . . . ?
N2 C9 C10 C11 -178.14(15) . . . . ?
C9 C10 C11 C6 -1.5(3) . . . . ?
C7 C6 C11 C10 -0.1(2) . . . . ?
C1 C6 C11 C10 178.48(15) . . . . ?
C9 N2 C12 C13 48.1(2) . . . . ?
C18 N2 C12 C13 -134.08(17) . . . . ?
C9 N2 C12 C17 -132.07(17) . . . . ?
C18 N2 C12 C17 45.8(2) . . . . ?
C17 C12 C13 C14 0.3(3) . . . . ?
N2 C12 C13 C14 -179.86(16) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C13 C14 C15 C24 -178.25(16) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C24 C15 C16 C17 179.34(16) . . . . ?
C15 C16 C17 C12 -1.1(3) . . . . ?
C13 C12 C17 C16 0.8(3) . . . . ?
N2 C12 C17 C16 -179.07(15) . . . . ?
C9 N2 C18 C23 33.4(2) . . . . ?
C12 N2 C18 C23 -144.37(17) . . . . ?
C9 N2 C18 C19 -147.46(16) . . . . ?
C12 N2 C18 C19 34.8(2) . . . . ?
C23 C18 C19 C20 1.4(3) . . . . ?
N2 C18 C19 C20 -177.72(16) . . . . ?
C18 C19 C20 C21 -1.7(3) . . . . ?
C19 C20 C21 C22 0.1(3) . . . . ?
C19 C20 C21 C29 178.41(16) . . . . ?
C20 C21 C22 C23 1.7(3) . . . . ?
C29 C21 C22 C23 -176.59(16) . . . . ?
C21 C22 C23 C18 -2.0(3) . . . . ?
C19 C18 C23 C22 0.4(3) . . . . ?
N2 C18 C23 C22 179.52(16) . . . . ?
C14 C15 C24 C28 -29.3(3) . . . . ?
C16 C15 C24 C28 151.69(17) . . . . ?
C14 C15 C24 C25 149.82(17) . . . . ?
C16 C15 C24 C25 -29.2(3) . . . . ?
C28 C24 C25 C26 -0.6(3) . . . . ?
C15 C24 C25 C26 -179.78(16) . . . . ?
C27 N3 C26 C25 -0.6(3) . . . . ?
C24 C25 C26 N3 1.4(3) . . . . ?
C26 N3 C27 C28 -0.9(3) . . . . ?
N3 C27 C28 C24 1.6(3) . . . . ?
C25 C24 C28 C27 -0.8(3) . . . . ?
C15 C24 C28 C27 178.42(16) . . . . ?
C22 C21 C29 C30 143.68(17) . . . . ?
C20 C21 C29 C30 -34.5(3) . . . . ?
C22 C21 C29 C33 -34.0(3) . . . . ?
C20 C21 C29 C33 147.78(17) . . . . ?
C33 C29 C30 C31 0.2(2) . . . . ?
C21 C29 C30 C31 -177.57(16) . . . . ?
C32 N4 C31 C30 -0.4(3) . . . . ?
C29 C30 C31 N4 0.4(3) . . . . ?
C31 N4 C32 C33 -0.2(3) . . . . ?
N4 C32 C33 C29 0.9(3) . . . . ?
C30 C29 C33 C32 -0.8(3) . . . . ?
C21 C29 C33 C32 176.99(16) . . . . ?
O1 C34 C35 C36 -3.7(3) . . . . ?
O3 C34 C35 C36 174.41(16) . . . . ?
O1 C34 C35 C40 178.73(18) . . . . ?
O3 C34 C35 C40 -3.2(3) . . . . ?
C40 C35 C36 C37 3.5(3) . . . . ?
C34 C35 C36 C37 -174.15(16) . . . . ?
C35 C36 C37 C38 -1.5(3) . . . . ?
C36 C37 C38 C39 -1.8(3) . . . . ?
C36 C37 C38 C41 177.19(17) . . . . ?
C37 C38 C39 C40 3.0(3) . . . . ?
C41 C38 C39 C40 -175.97(17) . . . . ?
C38 C39 C40 C35 -1.0(3) . . . . ?
C36 C35 C40 C39 -2.2(3) . . . . ?
C34 C35 C40 C39 175.33(17) . . . . ?
C37 C38 C41 O2 175.72(19) . . . . ?
C39 C38 C41 O2 -5.3(3) . . . . ?
C37 C38 C41 O4 -5.2(2) . . . . ?
C39 C38 C41 O4 173.74(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3A N1 0.84 1.76 2.584(2) 167.9 . yes
O4 H4A N4 0.84 1.76 2.588(2) 168.7 2_636 yes

####################################################################### 
# 
# 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_mo_0425_10_0m_sq
_database_code_depnum_ccdc_archive 'CCDC 2205392'
loop_
_audit_author_name
_audit_author_address
'Yanhong Liu'
;Tongji University
China
;
_audit_update_record             
;
2022-09-05 deposited with the CCDC.	2023-12-27 downloaded from the CCDC.
;
_audit_creation_date             2021-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 O6, C33 H24 N4'
_chemical_formula_sum            'C42 H30 N4 O6'
_chemical_formula_weight         686.70
_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                   11.6130(6)
_cell_length_b                   13.3303(7)
_cell_length_c                   15.7331(7)
_cell_angle_alpha                93.2781(19)
_cell_angle_beta                 102.0221(18)
_cell_angle_gamma                106.5566(19)
_cell_volume                     2265.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7608
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0840 before and 0.0710 after correction.
The Ratio of minimum to maximum transmission is 0.4058.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.007
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0855
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_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            61020
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.422
_diffrn_reflns_theta_min         2.035
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6350
_reflns_number_total             9238
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         9238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0587
_refine_ls_restrained_S_all      1.049
_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)+(0.1179P)²+0.1556P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1829
_refine_ls_wR_factor_ref         0.2016
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C40(H40), C38(H38), C36(H36), C17(H17), C25(H25), C24(H24), C27(H27),
 C21(H21), C30(H30), C8(H8), C20(H20), C33(H33), C11(H11), C14(H14), C10(H10),
 C28(H28), C13(H13), C16(H16), C22(H22), C32(H32), C7(H7), C2(H2), C19(H19),
 C31(H31), C4(H4), C5(H5), C1(H1)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O5(H5A), O4(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 1.14287(14) 0.25536(12) -0.05325(10) 0.0428(4) Uani 1 1 d . . . . .
O1 O 1.29795(14) 0.32620(11) 0.06440(9) 0.0386(3) Uani 1 1 d . . . . .
H1A H 1.277215 0.264822 0.078318 0.058 Uiso 1 1 calc GR . . . .
O3 O 1.56319(14) 0.69755(12) 0.08882(10) 0.0417(4) Uani 1 1 d . . . . .
O5 O 1.08469(16) 0.46383(15) -0.29363(11) 0.0525(4) Uani 1 1 d . . . . .
H5A H 1.038638 0.477066 -0.337402 0.079 Uiso 1 1 calc GR . . . .
O4 O 1.50415(15) 0.79504(12) -0.01307(12) 0.0497(4) Uani 1 1 d . . . . .
H4A H 1.565696 0.843030 0.016751 0.075 Uiso 1 1 calc GR . . . .
O6 O 1.18122(18) 0.63628(15) -0.27962(11) 0.0577(5) Uani 1 1 d . . . . .
N3 N 1.25872(19) 1.14137(15) 0.11824(13) 0.0442(4) Uani 1 1 d . . . . .
C35 C 1.26427(19) 0.43475(16) -0.04481(13) 0.0338(4) Uani 1 1 d . . . . .
C40 C 1.20018(19) 0.44509(17) -0.12711(13) 0.0354(4) Uani 1 1 d . . . . .
H40 H 1.134104 0.387009 -0.159628 0.042 Uiso 1 1 calc R . . . .
N2 N 1.27506(16) 0.53017(14) 0.23490(12) 0.0391(4) Uani 1 1 d . . . . .
C39 C 1.23171(19) 0.53944(18) -0.16233(14) 0.0375(5) Uani 1 1 d . . . . .
C38 C 1.32839(19) 0.62528(17) -0.11416(14) 0.0370(5) Uani 1 1 d . . . . .
H38 H 1.350198 0.690175 -0.137828 0.044 Uiso 1 1 calc R . . . .
C36 C 1.36071(19) 0.52002(16) 0.00317(13) 0.0341(4) Uani 1 1 d . . . . .
H36 H 1.404853 0.513294 0.059505 0.041 Uiso 1 1 calc R . . . .
C37 C 1.39235(19) 0.61531(16) -0.03166(14) 0.0351(4) Uani 1 1 d . . . . .
C23 C 1.17438(19) 0.43687(17) 0.20572(14) 0.0367(5) Uani 1 1 d . . . . .
C9 C 1.38753(19) 0.52330(17) 0.28912(14) 0.0371(5) Uani 1 1 d . . . . .
C18 C 1.2534(2) 0.93878(18) 0.15967(14) 0.0406(5) Uani 1 1 d . . . . .
C41 C 1.49620(19) 0.70677(17) 0.02148(15) 0.0370(5) Uani 1 1 d . . . . .
N4 N 0.68102(19) -0.03815(15) 0.06161(14) 0.0482(5) Uani 1 1 d . . . . .
C17 C 1.1564(2) 0.65553(18) 0.20722(16) 0.0427(5) Uani 1 1 d . . . . .
H17 H 1.084718 0.604975 0.215722 0.051 Uiso 1 1 calc R . . . .
C34 C 1.22790(19) 0.32927(16) -0.01211(13) 0.0347(4) Uani 1 1 d . . . . .
C25 C 1.0638(2) 0.26142(18) 0.22782(15) 0.0420(5) Uani 1 1 d . . . . .
H25 H 1.056462 0.205241 0.262862 0.050 Uiso 1 1 calc R . . . .
C26 C 0.97780(19) 0.24901(17) 0.14908(14) 0.0380(5) Uani 1 1 d . . . . .
C29 C 0.8746(2) 0.14998(17) 0.11995(15) 0.0395(5) Uani 1 1 d . . . . .
C12 C 1.2661(2) 0.63007(16) 0.21446(14) 0.0367(5) Uani 1 1 d . . . . .
C24 C 1.1601(2) 0.35399(18) 0.25627(15) 0.0412(5) Uani 1 1 d . . . . .
H24 H 1.216915 0.360968 0.310894 0.049 Uiso 1 1 calc R . . . .
C27 C 0.9925(2) 0.33269(18) 0.09845(15) 0.0400(5) Uani 1 1 d . . . . .
H27 H 0.934999 0.325920 0.044177 0.048 Uiso 1 1 calc R . . . .
C21 C 1.1554(2) 1.05878(18) 0.09161(15) 0.0430(5) Uani 1 1 d . . . . .
H21 H 1.083746 1.070548 0.057564 0.052 Uiso 1 1 calc R . . . .
C15 C 1.2561(2) 0.83138(17) 0.17784(14) 0.0400(5) Uani 1 1 d . . . . .
C30 C 0.8838(2) 0.05431(18) 0.14691(16) 0.0447(5) Uani 1 1 d . . . . .
H30 H 0.957082 0.052007 0.186037 0.054 Uiso 1 1 calc R . . . .
C8 C 1.4420(2) 0.59107(18) 0.36689(14) 0.0412(5) Uani 1 1 d . . . . .
H8 H 1.405307 0.642038 0.383486 0.049 Uiso 1 1 calc R . . . .
C20 C 1.3575(2) 1.12341(19) 0.16665(16) 0.0487(6) Uani 1 1 d . . . . .
H20 H 1.430558 1.181238 0.186926 0.058 Uiso 1 1 calc R . . . .
C42 C 1.1634(2) 0.5514(2) -0.25141(15) 0.0432(5) Uani 1 1 d . . . . .
C33 C 0.7642(2) 0.14802(18) 0.06311(16) 0.0437(5) Uani 1 1 d . . . . .
H33 H 0.752809 0.211246 0.043167 0.052 Uiso 1 1 calc R . . . .
C3 C 1.7171(2) 0.4991(2) 0.45706(14) 0.0432(5) Uani 1 1 d . . . . .
C11 C 1.5473(2) 0.44045(18) 0.32009(14) 0.0417(5) Uani 1 1 d . . . . .
H11 H 1.582075 0.387768 0.304202 0.050 Uiso 1 1 calc R . . . .
C14 C 1.3651(2) 0.80482(18) 0.18547(15) 0.0435(5) Uani 1 1 d . . . . .
H14 H 1.437425 0.855965 0.178522 0.052 Uiso 1 1 calc R . . . .
C10 C 1.4414(2) 0.44929(18) 0.26588(14) 0.0409(5) Uani 1 1 d . . . . .
H10 H 1.405357 0.404036 0.212219 0.049 Uiso 1 1 calc R . . . .
C28 C 1.0890(2) 0.42490(17) 0.12587(14) 0.0393(5) Uani 1 1 d . . . . .
H28 H 1.097401 0.480555 0.090286 0.047 Uiso 1 1 calc R . . . .
N1 N 1.92430(19) 0.4839(2) 0.57549(13) 0.0522(5) Uani 1 1 d . . . . .
C6 C 1.6036(2) 0.50827(19) 0.39798(14) 0.0407(5) Uani 1 1 d . . . . .
C13 C 1.3701(2) 0.70591(18) 0.20288(15) 0.0419(5) Uani 1 1 d . . . . .
H13 H 1.445291 0.689356 0.207013 0.050 Uiso 1 1 calc R . . . .
C16 C 1.1519(2) 0.75420(18) 0.18770(16) 0.0444(5) Uani 1 1 d . . . . .
H16 H 1.075835 0.769729 0.180843 0.053 Uiso 1 1 calc R . . . .
C22 C 1.1482(2) 0.95821(18) 0.11116(15) 0.0422(5) Uani 1 1 d . . . . .
H22 H 1.072751 0.902634 0.091929 0.051 Uiso 1 1 calc R . . . .
C32 C 0.6717(2) 0.05346(19) 0.03617(17) 0.0479(6) Uani 1 1 d . . . . .
H32 H 0.597186 0.053581 -0.002669 0.057 Uiso 1 1 calc R . . . .
C7 C 1.5498(2) 0.58389(19) 0.41991(15) 0.0448(5) Uani 1 1 d . . . . .
H7 H 1.587766 0.631425 0.472193 0.054 Uiso 1 1 calc R . . . .
C2 C 1.7358(2) 0.4024(2) 0.46908(16) 0.0503(6) Uani 1 1 d . . . . .
H2 H 1.677603 0.339699 0.436606 0.060 Uiso 1 1 calc R . . . .
C19 C 1.3595(2) 1.02595(19) 0.18889(16) 0.0483(6) Uani 1 1 d . . . . .
H19 H 1.432506 1.017442 0.223929 0.058 Uiso 1 1 calc R . . . .
C31 C 0.7869(2) -0.03738(19) 0.11697(17) 0.0487(6) Uani 1 1 d . . . . .
H31 H 0.795130 -0.101857 0.136050 0.058 Uiso 1 1 calc R . . . .
C4 C 1.8081(2) 0.5889(2) 0.50457(15) 0.0500(6) Uani 1 1 d . . . . .
H4 H 1.800329 0.657060 0.497073 0.060 Uiso 1 1 calc R . . . .
C5 C 1.9098(2) 0.5774(2) 0.56280(15) 0.0541(6) Uani 1 1 d . . . . .
H5 H 1.971263 0.638838 0.594716 0.065 Uiso 1 1 calc R . . . .
C1 C 1.8394(2) 0.3974(2) 0.52849(17) 0.0538(6) Uani 1 1 d . . . . .
H1 H 1.850879 0.330496 0.536282 0.065 Uiso 1 1 calc R . . . .


_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
O2 C34 1.213(2) . ?
O1 H1A 0.8400 . ?
O1 C34 1.315(2) . ?
O3 C41 1.212(3) . ?
O5 H5A 0.8400 . ?
O5 C42 1.300(3) . ?
O4 H4A 0.8400 . ?
O4 C41 1.312(3) . ?
O6 C42 1.217(3) . ?
N3 C21 1.346(3) . ?
N3 C20 1.329(3) . ?
C35 C40 1.388(3) . ?
C35 C36 1.393(3) . ?
C35 C34 1.502(3) . ?
C40 H40 0.9500 . ?
C40 C39 1.387(3) . ?
N2 C23 1.417(3) . ?
N2 C9 1.433(3) . ?
N2 C12 1.415(3) . ?
C39 C38 1.399(3) . ?
C39 C42 1.501(3) . ?
C38 H38 0.9500 . ?
C38 C37 1.389(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.395(3) . ?
C37 C41 1.505(3) . ?
C23 C24 1.390(3) . ?
C23 C28 1.398(3) . ?
C9 C8 1.392(3) . ?
C9 C10 1.380(3) . ?
C18 C15 1.484(3) . ?
C18 C22 1.398(3) . ?
C18 C19 1.403(3) . ?
N4 C32 1.333(3) . ?
N4 C31 1.347(3) . ?
C17 H17 0.9500 . ?
C17 C12 1.392(3) . ?
C17 C16 1.381(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.388(3) . ?
C25 C24 1.384(3) . ?
C26 C29 1.480(3) . ?
C26 C27 1.399(3) . ?
C29 C30 1.392(3) . ?
C29 C33 1.395(3) . ?
C12 C13 1.390(3) . ?
C24 H24 0.9500 . ?
C27 H27 0.9500 . ?
C27 C28 1.380(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.376(3) . ?
C15 C14 1.393(3) . ?
C15 C16 1.390(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.383(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.384(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.370(3) . ?
C33 H33 0.9500 . ?
C33 C32 1.378(3) . ?
C3 C6 1.487(3) . ?
C3 C2 1.384(4) . ?
C3 C4 1.398(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.383(3) . ?
C11 C6 1.396(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.377(3) . ?
C10 H10 0.9500 . ?
C28 H28 0.9500 . ?
N1 C5 1.326(4) . ?
N1 C1 1.341(4) . ?
C6 C7 1.390(3) . ?
C13 H13 0.9500 . ?
C16 H16 0.9500 . ?
C22 H22 0.9500 . ?
C32 H32 0.9500 . ?
C7 H7 0.9500 . ?
C2 H2 0.9500 . ?
C2 C1 1.382(3) . ?
C19 H19 0.9500 . ?
C31 H31 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C5 H5 0.9500 . ?
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
C34 O1 H1A 109.5 . . ?
C42 O5 H5A 109.5 . . ?
C41 O4 H4A 109.5 . . ?
C20 N3 C21 117.31(19) . . ?
C40 C35 C36 119.77(19) . . ?
C40 C35 C34 117.72(18) . . ?
C36 C35 C34 122.50(18) . . ?
C35 C40 H40 119.7 . . ?
C39 C40 C35 120.62(19) . . ?
C39 C40 H40 119.7 . . ?
C23 N2 C9 118.91(17) . . ?
C12 N2 C23 121.79(17) . . ?
C12 N2 C9 119.27(17) . . ?
C40 C39 C38 119.70(19) . . ?
C40 C39 C42 121.1(2) . . ?
C38 C39 C42 119.20(19) . . ?
C39 C38 H38 120.1 . . ?
C37 C38 C39 119.81(19) . . ?
C37 C38 H38 120.1 . . ?
C35 C36 H36 120.1 . . ?
C35 C36 C37 119.88(19) . . ?
C37 C36 H36 120.1 . . ?
C38 C37 C36 120.22(19) . . ?
C38 C37 C41 120.70(19) . . ?
C36 C37 C41 119.08(19) . . ?
C24 C23 N2 119.90(19) . . ?
C24 C23 C28 118.56(19) . . ?
C28 C23 N2 121.53(19) . . ?
C8 C9 N2 119.6(2) . . ?
C10 C9 N2 120.82(19) . . ?
C10 C9 C8 119.6(2) . . ?
C22 C18 C15 122.6(2) . . ?
C22 C18 C19 116.8(2) . . ?
C19 C18 C15 120.6(2) . . ?
O3 C41 O4 125.1(2) . . ?
O3 C41 C37 122.37(19) . . ?
O4 C41 C37 112.55(18) . . ?
C32 N4 C31 117.7(2) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C12 120.0(2) . . ?
O2 C34 O1 124.43(19) . . ?
O2 C34 C35 122.59(18) . . ?
O1 C34 C35 112.98(17) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C24 C25 C26 121.3(2) . . ?
C25 C26 C29 120.7(2) . . ?
C25 C26 C27 117.84(19) . . ?
C27 C26 C29 121.5(2) . . ?
C30 C29 C26 121.6(2) . . ?
C30 C29 C33 117.0(2) . . ?
C33 C29 C26 121.4(2) . . ?
C17 C12 N2 121.93(19) . . ?
C13 C12 N2 119.2(2) . . ?
C13 C12 C17 118.9(2) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.6(2) . . ?
C25 C24 H24 119.7 . . ?
C26 C27 H27 119.4 . . ?
C28 C27 C26 121.2(2) . . ?
C28 C27 H27 119.4 . . ?
N3 C21 H21 118.3 . . ?
N3 C21 C22 123.4(2) . . ?
C22 C21 H21 118.3 . . ?
C14 C15 C18 120.2(2) . . ?
C16 C15 C18 122.1(2) . . ?
C16 C15 C14 117.7(2) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 C29 120.3(2) . . ?
C31 C30 H30 119.8 . . ?
C9 C8 H8 120.1 . . ?
C7 C8 C9 119.7(2) . . ?
C7 C8 H8 120.1 . . ?
N3 C20 H20 118.2 . . ?
N3 C20 C19 123.5(2) . . ?
C19 C20 H20 118.2 . . ?
O5 C42 C39 113.7(2) . . ?
O6 C42 O5 124.4(2) . . ?
O6 C42 C39 121.9(2) . . ?
C29 C33 H33 120.3 . . ?
C32 C33 C29 119.3(2) . . ?
C32 C33 H33 120.3 . . ?
C2 C3 C6 121.9(2) . . ?
C2 C3 C4 117.4(2) . . ?
C4 C3 C6 120.7(2) . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C6 120.6(2) . . ?
C6 C11 H11 119.7 . . ?
C15 C14 H14 119.4 . . ?
C13 C14 C15 121.3(2) . . ?
C13 C14 H14 119.4 . . ?
C9 C10 C11 120.5(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C23 C28 H28 119.8 . . ?
C27 C28 C23 120.4(2) . . ?
C27 C28 H28 119.8 . . ?
C5 N1 C1 118.8(2) . . ?
C11 C6 C3 121.1(2) . . ?
C7 C6 C3 120.5(2) . . ?
C7 C6 C11 118.4(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.7 . . ?
C17 C16 C15 121.6(2) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C18 C22 H22 120.4 . . ?
C21 C22 C18 119.2(2) . . ?
C21 C22 H22 120.4 . . ?
N4 C32 C33 123.6(2) . . ?
N4 C32 H32 118.2 . . ?
C33 C32 H32 118.2 . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C3 C2 H2 120.1 . . ?
C1 C2 C3 119.8(2) . . ?
C1 C2 H2 120.1 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.7(2) . . ?
C20 C19 H19 120.1 . . ?
N4 C31 C30 122.1(2) . . ?
N4 C31 H31 119.0 . . ?
C30 C31 H31 119.0 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 122.4(3) . . ?
N1 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
N1 C1 C2 122.2(3) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?

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
N3 C21 C22 C18 -1.3(4) . . . . ?
N3 C20 C19 C18 0.3(4) . . . . ?
C35 C40 C39 C38 -0.5(3) . . . . ?
C35 C40 C39 C42 179.8(2) . . . . ?
C35 C36 C37 C38 -0.3(3) . . . . ?
C35 C36 C37 C41 179.55(19) . . . . ?
C40 C35 C36 C37 0.0(3) . . . . ?
C40 C35 C34 O2 -2.7(3) . . . . ?
C40 C35 C34 O1 176.86(19) . . . . ?
C40 C39 C38 C37 0.2(3) . . . . ?
C40 C39 C42 O5 -7.1(3) . . . . ?
C40 C39 C42 O6 172.4(2) . . . . ?
N2 C23 C24 C25 -178.6(2) . . . . ?
N2 C23 C28 C27 179.2(2) . . . . ?
N2 C9 C8 C7 179.3(2) . . . . ?
N2 C9 C10 C11 -177.6(2) . . . . ?
N2 C12 C13 C14 -178.1(2) . . . . ?
C39 C38 C37 C36 0.2(3) . . . . ?
C39 C38 C37 C41 -179.7(2) . . . . ?
C38 C39 C42 O5 173.1(2) . . . . ?
C38 C39 C42 O6 -7.4(3) . . . . ?
C38 C37 C41 O3 -171.1(2) . . . . ?
C38 C37 C41 O4 9.2(3) . . . . ?
C36 C35 C40 C39 0.4(3) . . . . ?
C36 C35 C34 O2 179.0(2) . . . . ?
C36 C35 C34 O1 -1.4(3) . . . . ?
C36 C37 C41 O3 9.0(3) . . . . ?
C36 C37 C41 O4 -170.61(19) . . . . ?
C23 N2 C9 C8 -129.7(2) . . . . ?
C23 N2 C9 C10 49.2(3) . . . . ?
C23 N2 C12 C17 33.9(3) . . . . ?
C23 N2 C12 C13 -147.4(2) . . . . ?
C9 N2 C23 C24 29.1(3) . . . . ?
C9 N2 C23 C28 -149.8(2) . . . . ?
C9 N2 C12 C17 -143.9(2) . . . . ?
C9 N2 C12 C13 34.8(3) . . . . ?
C9 C8 C7 C6 -1.5(4) . . . . ?
C18 C15 C14 C13 179.6(2) . . . . ?
C18 C15 C16 C17 -178.0(2) . . . . ?
C17 C12 C13 C14 0.7(3) . . . . ?
C34 C35 C40 C39 -178.0(2) . . . . ?
C34 C35 C36 C37 178.31(19) . . . . ?
C25 C26 C29 C30 -26.4(3) . . . . ?
C25 C26 C29 C33 154.5(2) . . . . ?
C25 C26 C27 C28 -0.3(3) . . . . ?
C26 C25 C24 C23 -1.1(4) . . . . ?
C26 C29 C30 C31 -178.5(2) . . . . ?
C26 C29 C33 C32 178.5(2) . . . . ?
C26 C27 C28 C23 -0.3(4) . . . . ?
C29 C26 C27 C28 -180.0(2) . . . . ?
C29 C30 C31 N4 -0.2(4) . . . . ?
C29 C33 C32 N4 0.2(4) . . . . ?
C12 N2 C23 C24 -148.7(2) . . . . ?
C12 N2 C23 C28 32.4(3) . . . . ?
C12 N2 C9 C8 48.1(3) . . . . ?
C12 N2 C9 C10 -132.9(2) . . . . ?
C12 C17 C16 C15 -2.3(4) . . . . ?
C24 C23 C28 C27 0.2(3) . . . . ?
C24 C25 C26 C29 -179.3(2) . . . . ?
C24 C25 C26 C27 1.0(3) . . . . ?
C27 C26 C29 C30 153.2(2) . . . . ?
C27 C26 C29 C33 -25.8(3) . . . . ?
C21 N3 C20 C19 1.3(4) . . . . ?
C15 C18 C22 C21 -175.3(2) . . . . ?
C15 C18 C19 C20 175.8(2) . . . . ?
C15 C14 C13 C12 -0.8(4) . . . . ?
C30 C29 C33 C32 -0.6(3) . . . . ?
C8 C9 C10 C11 1.4(3) . . . . ?
C20 N3 C21 C22 -0.8(4) . . . . ?
C42 C39 C38 C37 180.0(2) . . . . ?
C33 C29 C30 C31 0.6(3) . . . . ?
C3 C6 C7 C8 -177.9(2) . . . . ?
C3 C2 C1 N1 -0.3(4) . . . . ?
C3 C4 C5 N1 -0.1(4) . . . . ?
C11 C6 C7 C8 1.1(4) . . . . ?
C14 C15 C16 C17 2.1(4) . . . . ?
C10 C9 C8 C7 0.3(3) . . . . ?
C10 C11 C6 C3 179.6(2) . . . . ?
C10 C11 C6 C7 0.6(3) . . . . ?
C28 C23 C24 C25 0.4(3) . . . . ?
C6 C3 C2 C1 -176.3(2) . . . . ?
C6 C3 C4 C5 176.5(2) . . . . ?
C6 C11 C10 C9 -1.9(3) . . . . ?
C16 C17 C12 N2 179.6(2) . . . . ?
C16 C17 C12 C13 0.9(3) . . . . ?
C16 C15 C14 C13 -0.5(4) . . . . ?
C22 C18 C15 C14 148.1(2) . . . . ?
C22 C18 C15 C16 -31.8(3) . . . . ?
C22 C18 C19 C20 -2.3(4) . . . . ?
C32 N4 C31 C30 -0.3(4) . . . . ?
C2 C3 C6 C11 -36.1(3) . . . . ?
C2 C3 C6 C7 142.8(3) . . . . ?
C2 C3 C4 C5 -1.9(4) . . . . ?
C19 C18 C15 C14 -29.9(3) . . . . ?
C19 C18 C15 C16 150.1(2) . . . . ?
C19 C18 C22 C21 2.8(3) . . . . ?
C31 N4 C32 C33 0.3(4) . . . . ?
C4 C3 C6 C11 145.5(2) . . . . ?
C4 C3 C6 C7 -35.5(3) . . . . ?
C4 C3 C2 C1 2.1(4) . . . . ?
C5 N1 C1 C2 -1.8(4) . . . . ?
C1 N1 C5 C4 2.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
