# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1968485'
loop_
_audit_author_name
_audit_author_address
'Sadik Metin Ceyhan'
;Gebze Technical University
Turkey
;
_audit_update_record             
;
2019-11-27 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C27 H19 N O4, C27 H17 N O4'
_chemical_formula_sum            'C27 H18 N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         420.42

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   9.3467(10)
_cell_length_b                   15.2593(17)
_cell_length_c                   16.6257(18)
_cell_angle_alpha                66.179(7)
_cell_angle_beta                 79.925(8)
_cell_angle_gamma                88.526(9)
_cell_volume                     2133.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1966
_cell_measurement_theta_min      2.5138
_cell_measurement_theta_max      17.9948
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.178
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             876

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            28845
_diffrn_reflns_av_R_equivalents  0.0889
_diffrn_reflns_av_unetI/netI     0.0917
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             7498
_reflns_number_gt                3305
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1897
_refine_ls_R_factor_gt           0.0946
_refine_ls_wR_factor_gt          0.2608
_refine_ls_wR_factor_ref         0.3321
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_number_reflns         7498
_refine_ls_number_parameters     579
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1630P)²+0.3882P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.768
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.012(3)

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'

_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.8979(7) 0.6254(5) -0.0272(5) 0.106(2) Uani d . . . 1 . .
H H1A 0.8704 0.6427 -0.0845 0.159 Uiso calc U . R 1 . .
H H1B 0.9928 0.5999 -0.0281 0.159 Uiso calc U . R 1 . .
H H1C 0.8995 0.6812 -0.0142 0.159 Uiso calc U . R 1 . .
C C2 0.7944(6) 0.5541(4) 0.0404(4) 0.0866(18) Uani d . . . 1 . .
H H2A 0.8251 0.5331 0.0979 0.104 Uiso calc U . R 1 . .
H H2B 0.7884 0.4989 0.026 0.104 Uiso calc U . R 1 . .
C C3 0.5496(5) 0.5450(4) 0.1117(4) 0.0599(13) Uani d . . . 1 . .
C C4 0.4174(5) 0.5989(3) 0.1149(3) 0.0566(12) Uani d . . . 1 . .
C C5 0.4051(5) 0.6940(3) 0.0946(3) 0.0540(12) Uani d . . . 1 . .
C C6 0.5223(5) 0.7647(3) 0.0743(3) 0.0555(12) Uani d . . . 1 . .
C C7 0.6397(5) 0.7410(4) 0.1197(4) 0.0674(14) Uani d . . . 1 . .
H H7 0.6427 0.6794 0.1632 0.081 Uiso calc U . R 1 . .
C C8 0.7506(6) 0.8075(5) 0.1009(4) 0.0834(17) Uani d . . . 1 . .
H H8 0.8278 0.7911 0.1319 0.1 Uiso calc U . R 1 . .
C C9 0.7472(6) 0.8982(4) 0.0363(5) 0.0825(18) Uani d . . . 1 . .
H H9 0.8232 0.9428 0.0228 0.099 Uiso calc U . R 1 . .
C C10 0.6336(6) 0.9234(4) -0.0082(4) 0.0770(17) Uani d . . . 1 . .
H H10 0.6325 0.9852 -0.0518 0.092 Uiso calc U . R 1 . .
C C11 0.5195(5) 0.8580(3) 0.0107(4) 0.0683(15) Uani d . . . 1 . .
H H11 0.4412 0.8764 -0.0191 0.082 Uiso calc U . R 1 . .
C C12 0.2746(5) 0.5490(4) 0.1439(3) 0.0651(14) Uani d . . . 1 . .
C C13 0.1662(6) 0.6256(3) 0.1362(3) 0.0637(14) Uani d . . . 1 . .
C C14 0.2497(5) 0.7218(3) 0.0899(3) 0.0624(14) Uani d . . . 1 . .
C C15 0.2192(5) 0.7682(4) -0.0063(4) 0.0649(14) Uani d . . . 1 . .
C C16 0.2591(6) 0.7428(4) -0.0772(4) 0.0733(15) Uani d . . . 1 . .
H H16 0.3178 0.6914 -0.0725 0.088 Uiso calc U . R 1 . .
C C17 0.2097(7) 0.7957(5) -0.1555(4) 0.0873(18) Uani d . . . 1 . .
H H17 0.2336 0.7794 -0.2043 0.105 Uiso calc U . R 1 . .
C C18 0.1238(7) 0.8735(5) -0.1615(4) 0.094(2) Uani d . . . 1 . .
H H18 0.0888 0.9082 -0.2139 0.112 Uiso calc U . R 1 . .
C C19 0.0905(6) 0.8995(4) -0.0900(4) 0.0810(17) Uani d . . . 1 . .
H H19 0.0353 0.9521 -0.0937 0.097 Uiso calc U . R 1 . .
C C20 0.1420(5) 0.8446(4) -0.0133(4) 0.0662(14) Uani d . . . 1 . .
C C21 0.1823(5) 0.7949(4) 0.1221(4) 0.0628(14) Uani d . . . 1 . .
C C22 0.1739(6) 0.7852(4) 0.2152(3) 0.0664(14) Uani d . . . 1 . .
C C23 0.0827(7) 0.8429(4) 0.2472(4) 0.0919(19) Uani d . . . 1 . .
H H23 0.0316 0.8901 0.2093 0.11 Uiso calc U . R 1 . .
C C24 0.0694(10) 0.8292(6) 0.3349(6) 0.116(2) Uani d . . . 1 . .
H H24 0.0076 0.8671 0.3559 0.139 Uiso calc U . R 1 . .
C C25 0.1418(9) 0.7636(6) 0.3908(5) 0.105(2) Uani d . . . 1 . .
H H25 0.1314 0.7566 0.4497 0.126 Uiso calc U . R 1 . .
C C26 0.2276(8) 0.7087(5) 0.3630(4) 0.0926(19) Uani d . . . 1 . .
H H26 0.2773 0.6627 0.403 0.111 Uiso calc U . R 1 . .
C C27 0.2465(6) 0.7170(4) 0.2760(4) 0.0751(15) Uani d . . . 1 . .
H H27 0.3081 0.6768 0.2582 0.09 Uiso calc U . R 1 . .
C C28 0.9213(12) 0.5168(9) 0.3927(9) 0.206(6) Uani d . . . 1 . .
H H28A 0.9391 0.4523 0.4084 0.248 Uiso calc U . R 1 . .
H H28B 0.9979 0.561 0.3795 0.248 Uiso calc U . R 1 . .
C C29 0.7974(15) 0.5437(7) 0.3892(10) 0.209(6) Uani d . . . 1 . .
H H29 0.7717 0.6069 0.374 0.251 Uiso calc U . R 1 . .
C C30 0.5982(9) 0.4803(5) 0.3596(5) 0.099(2) Uani d . . . 1 . .
C C31 0.5012(7) 0.3958(4) 0.3791(4) 0.0755(16) Uani d . . . 1 . .
C C32 0.3460(8) 0.4075(5) 0.3879(5) 0.094(2) Uani d . . . 1 . .
C C33 0.2778(7) 0.3075(4) 0.4202(4) 0.0855(18) Uani d . . . 1 . .
C C35 0.5362(5) 0.3060(3) 0.3913(3) 0.0657(14) Uani d . . . 1 . .
C C36 0.6811(5) 0.2716(4) 0.3740(3) 0.0627(13) Uani d . . . 1 . .
C C37 0.7878(6) 0.3347(4) 0.3100(4) 0.0715(15) Uani d . . . 1 . .
H H37 0.7658 0.3974 0.2767 0.086 Uiso calc U . R 1 . .
C C38 0.9256(7) 0.3054(6) 0.2956(4) 0.0901(19) Uani d . . . 1 . .
H H38 0.9984 0.3487 0.2543 0.108 Uiso calc U . R 1 . .
C C39 0.9564(6) 0.2117(6) 0.3425(5) 0.093(2) Uani d . . . 1 . .
H H39 1.0506 0.192 0.3335 0.111 Uiso calc U . R 1 . .
C C40 0.8491(6) 0.1472(5) 0.4024(4) 0.0838(17) Uani d . . . 1 . .
H H40 0.87 0.0833 0.4316 0.101 Uiso calc U . R 1 . .
C C41 0.7123(5) 0.1757(4) 0.4195(4) 0.0686(15) Uani d . . . 1 . .
H H41 0.6402 0.132 0.4611 0.082 Uiso calc U . R 1 . .
C C43 0.4174(9) 0.2194(5) 0.6045(5) 0.108(2) Uani d . . . 1 . .
H H43 0.4294 0.2859 0.5799 0.13 Uiso calc U . R 1 . .
C C44 0.4178(8) 0.1657(9) 0.6998(7) 0.166(5) Uani d . . . 1 . .
H H44A 0.3387 0.1842 0.735 0.199 Uiso calc U . R 1 . .
H H44B 0.5088 0.1784 0.7145 0.199 Uiso calc U . R 1 . .
C C45 0.3979(7) 0.0530(7) 0.7205(5) 0.120(3) Uani d . . . 1 . .
H H45 0.402 0.005 0.7765 0.144 Uiso calc U . R 1 . .
C C46 0.3754(9) 0.0332(6) 0.6526(5) 0.110(3) Uani d . . . 1 . .
C C47 0.4013(9) 0.1777(9) 0.5552(7) 0.118(3) Uani d . . . 1 . .
C C48 0.3723(9) 0.0951(10) 0.5768(8) 0.137(3) Uani d . . . 1 . .
C C49 0.3724(7) 0.1531(6) 0.4431(10) 0.183(7) Uani d . . . 1 . .
C C50 0.3554(7) 0.1629(9) 0.3433(5) 0.146(5) Uani d . . . 1 . .
C C51 0.3832(6) 0.2464(4) 0.2546(5) 0.0762(16) Uani d . . . 1 . .
H H51 0.4234 0.3033 0.2509 0.091 Uiso calc U . R 1 . .
C C52 0.3556(10) 0.2432(10) 0.1871(7) 0.141(4) Uani d . . . 1 . .
H H52 0.3683 0.2994 0.1353 0.169 Uiso calc U . R 1 . .
C C53 0.3150(14) 0.1754(8) 0.1835(9) 0.148(4) Uani d . . . 1 . .
H H53 0.3008 0.181 0.1276 0.178 Uiso calc U . R 1 . .
C C54 0.2865(8) 0.0922(5) 0.2478(5) 0.097(2) Uani d . . . 1 . .
H H54 0.255 0.0433 0.2342 0.116 Uiso calc U . R 1 . .
C C55 0.2983(7) 0.0704(5) 0.3315(5) 0.098(2) Uani d . . . 1 . .
H H55 0.2766 0.0099 0.3776 0.118 Uiso calc U . R 1 . .
N N1 0.1188(4) 0.8607(3) 0.0688(3) 0.0721(13) Uani d . . . 1 . .
N N2 0.3416(5) 0.0751(4) 0.4844(3) 0.0871(15) Uani d . . . 1 . .
O O1 0.0364(4) 0.6115(3) 0.1603(3) 0.0868(12) Uani d . . . 1 . .
O O2 0.2416(4) 0.4661(3) 0.1656(3) 0.0934(13) Uani d . . . 1 . .
O O3 0.5599(4) 0.4647(3) 0.1620(3) 0.0915(13) Uani d . . . 1 . .
O O4 0.6530(4) 0.5957(2) 0.0448(2) 0.0696(10) Uani d . . . 1 . .
O O5 0.6928(6) 0.4610(3) 0.4129(4) 0.1148(16) Uani d . . . 1 . .
O O6 0.5823(8) 0.5572(3) 0.3050(4) 0.159(3) Uani d . . . 1 . .
O O7 0.2791(6) 0.4776(4) 0.3751(4) 0.146(2) Uani d . . . 1 . .
O O8 0.1525(5) 0.2876(3) 0.4404(3) 0.1107(16) Uani d . . . 1 . .
C C34 0.4042(6) 0.2401(4) 0.4256(6) 0.122(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.438(8) ?
C1 H1A . 0.96 ?
C1 H1B . 0.96 ?
C1 H1C . 0.96 ?
C2 O4 . 1.454(6) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C3 O3 . 1.186(5) ?
C3 O4 . 1.318(6) ?
C3 C4 . 1.472(7) ?
C4 C5 . 1.357(6) ?
C4 C12 . 1.457(6) ?
C5 C6 . 1.454(6) ?
C5 C14 . 1.509(6) ?
C6 C11 . 1.392(6) ?
C6 C7 . 1.398(7) ?
C7 C8 . 1.374(7) ?
C7 H7 . 0.93 ?
C8 C9 . 1.371(8) ?
C8 H8 . 0.93 ?
C9 C10 . 1.359(8) ?
C9 H9 . 0.93 ?
C10 C11 . 1.384(7) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C12 O2 . 1.199(5) ?
C12 C13 . 1.508(7) ?
C13 O1 . 1.206(5) ?
C13 C14 . 1.514(7) ?
C14 C21 . 1.502(7) ?
C14 C15 . 1.542(7) ?
C15 C20 . 1.331(7) ?
C15 C16 . 1.373(7) ?
C16 C17 . 1.379(8) ?
C16 H16 . 0.93 ?
C17 C18 . 1.396(9) ?
C17 H17 . 0.93 ?
C18 C19 . 1.382(9) ?
C18 H18 . 0.93 ?
C19 C20 . 1.376(7) ?
C19 H19 . 0.93 ?
C20 N1 . 1.461(7) ?
C21 N1 . 1.258(6) ?
C21 C22 . 1.482(7) ?
C22 C27 . 1.386(7) ?
C22 C23 . 1.402(8) ?
C23 C24 . 1.369(10) ?
C23 H23 . 0.93 ?
C24 C25 . 1.325(10) ?
C24 H24 . 0.93 ?
C25 C26 . 1.307(9) ?
C25 H25 . 0.93 ?
C26 C27 . 1.379(8) ?
C26 H26 . 0.93 ?
C27 H27 . 0.93 ?
C28 C29 . 1.222(13) ?
C28 H28A . 0.93 ?
C28 H28B . 0.93 ?
C29 O5 . 1.493(11) ?
C29 H29 . 0.93 ?
C30 O6 . 1.183(7) ?
C30 O5 . 1.304(8) ?
C30 C31 . 1.487(8) ?
C31 C35 . 1.343(7) ?
C31 C32 . 1.446(8) ?
C32 O7 . 1.186(7) ?
C32 C33 . 1.513(9) ?
C33 O8 . 1.173(7) ?
C33 C34 . 1.537(8) ?
C35 C36 . 1.464(7) ?
C35 C34 . 1.487(8) ?
C36 C37 . 1.380(7) ?
C36 C41 . 1.399(7) ?
C37 C38 . 1.365(8) ?
C37 H37 . 0.93 ?
C38 C39 . 1.376(8) ?
C38 H38 . 0.93 ?
C39 C40 . 1.369(8) ?
C39 H39 . 0.93 ?
C40 C41 . 1.360(7) ?
C40 H40 . 0.93 ?
C41 H41 . 0.93 ?
C43 C47 . 1.251(11) ?
C43 C44 . 1.462(11) ?
C43 H43 . 0.93 ?
C44 C45 . 1.621(12) ?
C44 H44A . 0.97 ?
C44 H44B . 0.97 ?
C45 C46 . 1.330(11) ?
C45 H45 . 0.93 ?
C46 C48 . 1.238(12) ?
C47 C48 . 1.187(12) ?
C47 C34 . 1.969(13) ?
C48 N2 . 1.753(13) ?
C49 N2 . 1.122(9) ?
C49 C34 . 1.270(9) ?
C49 C50 . 1.640(15) ?
C50 C51 . 1.493(11) ?
C50 C55 . 1.618(12) ?
C51 C52 . 1.215(11) ?
C51 H51 . 0.93 ?
C52 C53 . 1.138(12) ?
C52 H52 . 0.93 ?
C53 C54 . 1.284(12) ?
C53 H53 . 0.93 ?
C54 C55 . 1.318(9) ?
C54 H54 . 0.93 ?
C55 H55 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C1 C2 O4 . . 108.9(5) ?
C1 C2 H2A . . 109.9 ?
O4 C2 H2A . . 109.9 ?
C1 C2 H2B . . 109.9 ?
O4 C2 H2B . . 109.9 ?
H2A C2 H2B . . 108.3 ?
O3 C3 O4 . . 124.2(5) ?
O3 C3 C4 . . 123.8(5) ?
O4 C3 C4 . . 112.0(4) ?
C5 C4 C12 . . 111.0(4) ?
C5 C4 C3 . . 129.1(4) ?
C12 C4 C3 . . 120.0(4) ?
C4 C5 C6 . . 127.1(4) ?
C4 C5 C14 . . 111.1(4) ?
C6 C5 C14 . . 121.8(4) ?
C11 C6 C7 . . 118.2(4) ?
C11 C6 C5 . . 121.2(4) ?
C7 C6 C5 . . 120.6(4) ?
C8 C7 C6 . . 120.9(5) ?
C8 C7 H7 . . 119.6 ?
C6 C7 H7 . . 119.6 ?
C9 C8 C7 . . 119.8(5) ?
C9 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
C10 C9 C8 . . 120.5(5) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C9 C10 C11 . . 120.7(5) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C10 C11 C6 . . 119.9(5) ?
C10 C11 H11 . . 120.0 ?
C6 C11 H11 . . 120.0 ?
O2 C12 C4 . . 130.3(5) ?
O2 C12 C13 . . 123.9(5) ?
C4 C12 C13 . . 105.6(4) ?
O1 C13 C12 . . 125.4(4) ?
O1 C13 C14 . . 127.1(5) ?
C12 C13 C14 . . 107.6(4) ?
C21 C14 C5 . . 122.8(4) ?
C21 C14 C13 . . 112.3(4) ?
C5 C14 C13 . . 102.4(4) ?
C21 C14 C15 . . 98.1(4) ?
C5 C14 C15 . . 113.4(4) ?
C13 C14 C15 . . 107.5(4) ?
C20 C15 C16 . . 121.8(5) ?
C20 C15 C14 . . 107.4(5) ?
C16 C15 C14 . . 130.7(5) ?
C15 C16 C17 . . 118.1(6) ?
C15 C16 H16 . . 121.0 ?
C17 C16 H16 . . 121.0 ?
C16 C17 C18 . . 120.0(6) ?
C16 C17 H17 . . 120.0 ?
C18 C17 H17 . . 120.0 ?
C19 C18 C17 . . 120.4(6) ?
C19 C18 H18 . . 119.8 ?
C17 C18 H18 . . 119.8 ?
C20 C19 C18 . . 117.6(6) ?
C20 C19 H19 . . 121.2 ?
C18 C19 H19 . . 121.2 ?
C15 C20 C19 . . 122.0(6) ?
C15 C20 N1 . . 112.3(5) ?
C19 C20 N1 . . 125.6(6) ?
N1 C21 C22 . . 120.4(5) ?
N1 C21 C14 . . 116.6(5) ?
C22 C21 C14 . . 122.6(5) ?
C27 C22 C23 . . 116.6(5) ?
C27 C22 C21 . . 123.2(5) ?
C23 C22 C21 . . 120.1(5) ?
C24 C23 C22 . . 119.4(6) ?
C24 C23 H23 . . 120.3 ?
C22 C23 H23 . . 120.3 ?
C25 C24 C23 . . 122.1(7) ?
C25 C24 H24 . . 119.0 ?
C23 C24 H24 . . 119.0 ?
C26 C25 C24 . . 120.0(7) ?
C26 C25 H25 . . 120.0 ?
C24 C25 H25 . . 120.0 ?
C25 C26 C27 . . 121.8(7) ?
C25 C26 H26 . . 119.1 ?
C27 C26 H26 . . 119.1 ?
C26 C27 C22 . . 120.0(6) ?
C26 C27 H27 . . 120.0 ?
C22 C27 H27 . . 120.0 ?
C29 C28 H28A . . 120.0 ?
C29 C28 H28B . . 120.0 ?
H28A C28 H28B . . 120.0 ?
C28 C29 O5 . . 110.7(10) ?
C28 C29 H29 . . 124.7 ?
O5 C29 H29 . . 124.7 ?
O6 C30 O5 . . 125.2(7) ?
O6 C30 C31 . . 122.0(7) ?
O5 C30 C31 . . 112.7(6) ?
C35 C31 C32 . . 112.6(5) ?
C35 C31 C30 . . 129.1(6) ?
C32 C31 C30 . . 118.3(6) ?
O7 C32 C31 . . 130.3(7) ?
O7 C32 C33 . . 124.4(6) ?
C31 C32 C33 . . 105.4(5) ?
O8 C33 C32 . . 125.1(6) ?
O8 C33 C34 . . 128.4(6) ?
C32 C33 C34 . . 106.5(5) ?
C31 C35 C36 . . 127.6(5) ?
C31 C35 C34 . . 111.0(5) ?
C36 C35 C34 . . 121.4(5) ?
C37 C36 C41 . . 119.6(5) ?
C37 C36 C35 . . 119.1(5) ?
C41 C36 C35 . . 121.3(4) ?
C38 C37 C36 . . 120.1(6) ?
C38 C37 H37 . . 119.9 ?
C36 C37 H37 . . 119.9 ?
C37 C38 C39 . . 119.8(6) ?
C37 C38 H38 . . 120.1 ?
C39 C38 H38 . . 120.1 ?
C40 C39 C38 . . 120.4(6) ?
C40 C39 H39 . . 119.8 ?
C38 C39 H39 . . 119.8 ?
C41 C40 C39 . . 120.6(6) ?
C41 C40 H40 . . 119.7 ?
C39 C40 H40 . . 119.7 ?
C40 C41 C36 . . 119.4(5) ?
C40 C41 H41 . . 120.3 ?
C36 C41 H41 . . 120.3 ?
C47 C43 C44 . . 121.4(8) ?
C47 C43 H43 . . 119.3 ?
C44 C43 H43 . . 119.3 ?
C43 C44 C45 . . 106.9(6) ?
C43 C44 H44A . . 110.3 ?
C45 C44 H44A . . 110.3 ?
C43 C44 H44B . . 110.3 ?
C45 C44 H44B . . 110.3 ?
H44A C44 H44B . . 108.6 ?
C46 C45 C44 . . 116.1(7) ?
C46 C45 H45 . . 122.0 ?
C44 C45 H45 . . 122.0 ?
C48 C46 C45 . . 123.7(10) ?
C48 C47 C43 . . 127.9(12) ?
C48 C47 C34 . . 106.1(9) ?
C43 C47 C34 . . 125.9(10) ?
C47 C48 C46 . . 123.2(13) ?
C47 C48 N2 . . 110.1(11) ?
C46 C48 N2 . . 126.5(11) ?
N2 C49 C34 . . 158.5(15) ?
N2 C49 C50 . . 101.4(9) ?
C34 C49 C50 . . 99.8(10) ?
C51 C50 C55 . . 109.5(5) ?
C51 C50 C49 . . 131.2(9) ?
C55 C50 C49 . . 119.3(8) ?
C52 C51 C50 . . 122.9(9) ?
C52 C51 H51 . . 118.6 ?
C50 C51 H51 . . 118.6 ?
C53 C52 C51 . . 123.9(15) ?
C53 C52 H52 . . 118.1 ?
C51 C52 H52 . . 118.1 ?
C52 C53 C54 . . 127.3(15) ?
C52 C53 H53 . . 116.3 ?
C54 C53 H53 . . 116.3 ?
C53 C54 C55 . . 125.3(8) ?
C53 C54 H54 . . 117.4 ?
C55 C54 H54 . . 117.4 ?
C54 C55 C50 . . 111.0(6) ?
C54 C55 H55 . . 124.5 ?
C50 C55 H55 . . 124.5 ?
C21 N1 C20 . . 105.3(5) ?
C49 N2 C48 . . 87.1(9) ?
C3 O4 C2 . . 117.0(4) ?
C30 O5 C29 . . 112.8(6) ?
C49 C34 C35 . . 137.9(6) ?
C49 C34 C33 . . 117.3(6) ?
C35 C34 C33 . . 103.8(5) ?
C49 C34 C47 . . 77.9(8) ?
C35 C34 C47 . . 103.6(6) ?
C33 C34 C47 . . 102.0(5) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O3 C3 C4 C5 . . . . 146.6(6) ?
O4 C3 C4 C5 . . . . -35.4(7) ?
O3 C3 C4 C12 . . . . -32.8(8) ?
O4 C3 C4 C12 . . . . 145.2(5) ?
C12 C4 C5 C6 . . . . 171.6(5) ?
C3 C4 C5 C6 . . . . -7.9(9) ?
C12 C4 C5 C14 . . . . -11.6(6) ?
C3 C4 C5 C14 . . . . 168.9(5) ?
C4 C5 C6 C11 . . . . 143.8(5) ?
C14 C5 C6 C11 . . . . -32.7(7) ?
C4 C5 C6 C7 . . . . -37.4(8) ?
C14 C5 C6 C7 . . . . 146.1(5) ?
C11 C6 C7 C8 . . . . -1.1(8) ?
C5 C6 C7 C8 . . . . -180.0(5) ?
C6 C7 C8 C9 . . . . -0.5(8) ?
C7 C8 C9 C10 . . . . 1.2(9) ?
C8 C9 C10 C11 . . . . -0.2(9) ?
C9 C10 C11 C6 . . . . -1.6(8) ?
C7 C6 C11 C10 . . . . 2.2(8) ?
C5 C6 C11 C10 . . . . -179.0(5) ?
C5 C4 C12 O2 . . . . 178.5(6) ?
C3 C4 C12 O2 . . . . -2.0(9) ?
C5 C4 C12 C13 . . . . 2.2(6) ?
C3 C4 C12 C13 . . . . -178.2(4) ?
O2 C12 C13 O1 . . . . 9.2(9) ?
C4 C12 C13 O1 . . . . -174.3(5) ?
O2 C12 C13 C14 . . . . -168.8(5) ?
C4 C12 C13 C14 . . . . 7.8(5) ?
C4 C5 C14 C21 . . . . 142.8(5) ?
C6 C5 C14 C21 . . . . -40.2(7) ?
C4 C5 C14 C13 . . . . 15.7(5) ?
C6 C5 C14 C13 . . . . -167.3(4) ?
C4 C5 C14 C15 . . . . -99.8(5) ?
C6 C5 C14 C15 . . . . 77.2(6) ?
O1 C13 C14 C21 . . . . 34.9(7) ?
C12 C13 C14 C21 . . . . -147.2(4) ?
O1 C13 C14 C5 . . . . 168.5(5) ?
C12 C13 C14 C5 . . . . -13.7(5) ?
O1 C13 C14 C15 . . . . -71.9(7) ?
C12 C13 C14 C15 . . . . 106.0(5) ?
C21 C14 C15 C20 . . . . -4.0(5) ?
C5 C14 C15 C20 . . . . -135.1(4) ?
C13 C14 C15 C20 . . . . 112.5(5) ?
C21 C14 C15 C16 . . . . 175.5(5) ?
C5 C14 C15 C16 . . . . 44.4(7) ?
C13 C14 C15 C16 . . . . -68.0(6) ?
C20 C15 C16 C17 . . . . -3.7(7) ?
C14 C15 C16 C17 . . . . 176.8(5) ?
C15 C16 C17 C18 . . . . 1.1(8) ?
C16 C17 C18 C19 . . . . 1.4(9) ?
C17 C18 C19 C20 . . . . -1.5(9) ?
C16 C15 C20 C19 . . . . 3.8(8) ?
C14 C15 C20 C19 . . . . -176.7(4) ?
C16 C15 C20 N1 . . . . -177.0(4) ?
C14 C15 C20 N1 . . . . 2.6(5) ?
C18 C19 C20 C15 . . . . -1.1(8) ?
C18 C19 C20 N1 . . . . 179.8(5) ?
C5 C14 C21 N1 . . . . 129.3(5) ?
C13 C14 C21 N1 . . . . -108.1(5) ?
C15 C14 C21 N1 . . . . 4.7(5) ?
C5 C14 C21 C22 . . . . -58.0(6) ?
C13 C14 C21 C22 . . . . 64.7(6) ?
C15 C14 C21 C22 . . . . 177.4(4) ?
N1 C21 C22 C27 . . . . -177.1(5) ?
C14 C21 C22 C27 . . . . 10.4(7) ?
N1 C21 C22 C23 . . . . 6.7(7) ?
C14 C21 C22 C23 . . . . -165.8(5) ?
C27 C22 C23 C24 . . . . -0.3(9) ?
C21 C22 C23 C24 . . . . 176.1(6) ?
C22 C23 C24 C25 . . . . 0.9(12) ?
C23 C24 C25 C26 . . . . -0.9(13) ?
C24 C25 C26 C27 . . . . 0.3(11) ?
C25 C26 C27 C22 . . . . 0.2(9) ?
C23 C22 C27 C26 . . . . -0.2(8) ?
C21 C22 C27 C26 . . . . -176.5(5) ?
O6 C30 C31 C35 . . . . 136.0(8) ?
O5 C30 C31 C35 . . . . -48.4(9) ?
O6 C30 C31 C32 . . . . -44.8(10) ?
O5 C30 C31 C32 . . . . 130.8(7) ?
C35 C31 C32 O7 . . . . -173.9(7) ?
C30 C31 C32 O7 . . . . 6.8(11) ?
C35 C31 C32 C33 . . . . 7.2(7) ?
C30 C31 C32 C33 . . . . -172.1(5) ?
O7 C32 C33 O8 . . . . -4.1(12) ?
C31 C32 C33 O8 . . . . 174.9(7) ?
O7 C32 C33 C34 . . . . 179.0(7) ?
C31 C32 C33 C34 . . . . -2.0(7) ?
C32 C31 C35 C36 . . . . 169.7(5) ?
C30 C31 C35 C36 . . . . -11.1(10) ?
C32 C31 C35 C34 . . . . -9.7(8) ?
C30 C31 C35 C34 . . . . 169.6(7) ?
C31 C35 C36 C37 . . . . -26.8(8) ?
C34 C35 C36 C37 . . . . 152.6(6) ?
C31 C35 C36 C41 . . . . 154.8(6) ?
C34 C35 C36 C41 . . . . -25.9(8) ?
C41 C36 C37 C38 . . . . -4.5(8) ?
C35 C36 C37 C38 . . . . 177.0(5) ?
C36 C37 C38 C39 . . . . 2.6(9) ?
C37 C38 C39 C40 . . . . 1.1(10) ?
C38 C39 C40 C41 . . . . -3.1(9) ?
C39 C40 C41 C36 . . . . 1.2(9) ?
C37 C36 C41 C40 . . . . 2.5(8) ?
C35 C36 C41 C40 . . . . -179.0(5) ?
C47 C43 C44 C45 . . . . 1.1(10) ?
C43 C44 C45 C46 . . . . -4.7(9) ?
C44 C45 C46 C48 . . . . 1.6(12) ?
C44 C43 C47 C48 . . . . 7.1(15) ?
C44 C43 C47 C34 . . . . -178.1(6) ?
C43 C47 C48 C46 . . . . -11.7(18) ?
C34 C47 C48 C46 . . . . 172.7(8) ?
C43 C47 C48 N2 . . . . 173.3(8) ?
C34 C47 C48 N2 . . . . -2.3(9) ?
C45 C46 C48 C47 . . . . 6.5(16) ?
C45 C46 C48 N2 . . . . -179.3(7) ?
N2 C49 C50 C51 . . . . -178.0(6) ?
C34 C49 C50 C51 . . . . 5.6(8) ?
N2 C49 C50 C55 . . . . 2.5(7) ?
C34 C49 C50 C55 . . . . -173.9(5) ?
C55 C50 C51 C52 . . . . 4.6(9) ?
C49 C50 C51 C52 . . . . -174.9(7) ?
C50 C51 C52 C53 . . . . -5.2(16) ?
C51 C52 C53 C54 . . . . 2.(2) ?
C52 C53 C54 C55 . . . . 1.(2) ?
C53 C54 C55 C50 . . . . -0.5(11) ?
C51 C50 C55 C54 . . . . -1.8(7) ?
C49 C50 C55 C54 . . . . 177.8(5) ?
C22 C21 N1 C20 . . . . -176.3(4) ?
C14 C21 N1 C20 . . . . -3.4(5) ?
C15 C20 N1 C21 . . . . 0.3(6) ?
C19 C20 N1 C21 . . . . 179.5(5) ?
C34 C49 N2 C48 . . . . -9.7(19) ?
C50 C49 N2 C48 . . . . 180.0(5) ?
C47 C48 N2 C49 . . . . 3.9(9) ?
C46 C48 N2 C49 . . . . -170.9(9) ?
O3 C3 O4 C2 . . . . -8.6(8) ?
C4 C3 O4 C2 . . . . 173.4(4) ?
C1 C2 O4 C3 . . . . -170.6(5) ?
O6 C30 O5 C29 . . . . -8.8(13) ?
C31 C30 O5 C29 . . . . 175.8(8) ?
C28 C29 O5 C30 . . . . -136.3(12) ?
N2 C49 C34 C35 . . . . 105.(2) ?
C50 C49 C34 C35 . . . . -84.4(13) ?
N2 C49 C34 C33 . . . . -89.(2) ?
C50 C49 C34 C33 . . . . 81.4(9) ?
N2 C49 C34 C47 . . . . 8.4(18) ?
C50 C49 C34 C47 . . . . 178.7(4) ?
C31 C35 C34 C49 . . . . 174.7(14) ?
C36 C35 C34 C49 . . . . -4.7(18) ?
C31 C35 C34 C33 . . . . 7.7(8) ?
C36 C35 C34 C33 . . . . -171.7(5) ?
C31 C35 C34 C47 . . . . -98.5(6) ?
C36 C35 C34 C47 . . . . 82.1(7) ?
O8 C33 C34 C49 . . . . 9.9(15) ?
C32 C33 C34 C49 . . . . -173.3(10) ?
O8 C33 C34 C35 . . . . -179.8(7) ?
C32 C33 C34 C35 . . . . -3.1(8) ?
O8 C33 C34 C47 . . . . -72.5(9) ?
C32 C33 C34 C47 . . . . 104.3(6) ?

