# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_115MGL18
_database_code_depnum_ccdc_archive 'CCDC 1995525'
loop_
_audit_author_name
_audit_author_address
'Simon '
;UNAM
Mexico
;
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H36 N2 O4'
_chemical_formula_sum            'C33 H36 N2 O4'
_chemical_formula_weight         524.64

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.0933(12)
_cell_length_b                   16.561(3)
_cell_length_c                   19.628(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2956.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9942
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      68.35

_exptl_crystal_description       Prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.616
_shelx_estimated_absorpt_T_min   0.837
_shelx_estimated_absorpt_T_max   0.887
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.8232
_exptl_absorpt_correction_T_max  0.8643
_exptl_absorpt_process_details   'SHELXTL (Sheldrick, 2014)'
_exptl_absorpt_special_details   'face indexed-numerical'
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_measurement_device_type  
;Bruker D8 Venture κ-geometry diffractometer 208039-01
;
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            19335
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.492
_diffrn_reflns_theta_max         68.320
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5397
_reflns_number_gt                4678
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; Isopropylphenyl fragment is disordered and was refined 
anisotropically and modeled in two contributors using a 
variable site occupational factor (SOF).
The ratio of SOF was 50/50 for disorderd atoms.
308 restrictions were appplied as follow:
246 for SIMU, 40 for DELU, 20 for SAME/SADI and 2 for
DFIX intructions.

 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       'APEX3 v2016.1 (Bruker, 2014)'
_computing_cell_refinement       'APEX3 v2016.1 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.37A  (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2014 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
; 
Ortep-3 Ver 2.02 L.J. Farrugia (1997) J. Appl. Cryst. 30, 565 
;
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0786P)²+0.4113P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1681 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.01(13)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5397
_refine_ls_number_parameters     436
_refine_ls_number_restraints     308
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1505
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0142(3) 0.27247(13) 0.27020(12) 0.0691(6) Uani 1 1 d . . . . .
O2 O 0.6637(3) 0.42031(18) 0.27521(17) 0.0910(9) Uani 1 1 d . . . . .
O3 O 0.6244(3) 0.34393(14) 0.65494(12) 0.0654(6) Uani 1 1 d D . . . .
H3 H 0.611(5) 0.2967(12) 0.669(2) 0.078 Uiso 1 1 d D U . . .
O4 O 0.7886(3) 0.21283(16) 0.63050(13) 0.0753(7) Uani 1 1 d . . . . .
C1 C 0.8995(4) 0.47855(19) 0.25080(17) 0.0606(8) Uani 1 1 d . . . . .
H1 H 0.9318 0.5158 0.2150 0.073 Uiso 1 1 calc R U . . .
N2 N 0.9603(3) 0.39847(16) 0.23594(13) 0.0614(7) Uani 1 1 d . . . . .
C3 C 0.9776(4) 0.34181(19) 0.28490(16) 0.0587(7) Uani 1 1 d . . . . .
C4 C 0.9484(4) 0.36849(19) 0.35622(16) 0.0575(7) Uani 1 1 d . . . . .
C5 C 1.0232(5) 0.4828(2) 0.4343(2) 0.0759(10) Uani 1 1 d . . . . .
H5 H 1.0403 0.4464 0.4696 0.091 Uiso 1 1 calc R U . . .
C6 C 1.0468(6) 0.5641(3) 0.4444(2) 0.0920(13) Uani 1 1 d . . . . .
H6 H 1.0794 0.5824 0.4866 0.110 Uiso 1 1 calc R U . . .
C7 C 1.0223(6) 0.6190(3) 0.3923(3) 0.0943(14) Uani 1 1 d . . . . .
H7 H 1.0363 0.6740 0.3997 0.113 Uiso 1 1 calc R U . . .
C8 C 0.9771(5) 0.5915(2) 0.3294(2) 0.0788(10) Uani 1 1 d . . . . .
H8 H 0.9617 0.6281 0.2942 0.095 Uiso 1 1 calc R U . . .
C9 C 0.9546(4) 0.5100(2) 0.31843(18) 0.0625(8) Uani 1 1 d . . . . .
C10 C 0.9735(4) 0.45478(19) 0.37093(17) 0.0609(8) Uani 1 1 d . . . . .
C11 C 0.7304(4) 0.4768(2) 0.25109(18) 0.0655(8) Uani 1 1 d . . . . .
N12 N 0.6691(4) 0.54191(18) 0.22370(17) 0.0707(8) Uani 1 1 d D . . . .
H12 H 0.726(4) 0.5834(19) 0.210(2) 0.085 Uiso 1 1 d D U . . .
C13 C 0.5142(5) 0.5530(3) 0.2149(2) 0.0804(11) Uani 1 1 d . . . . .
H13 H 0.4635 0.5266 0.2529 0.096 Uiso 1 1 calc R U . . .
C14 C 0.4753(5) 0.6420(3) 0.2159(3) 0.0919(12) Uani 1 1 d . . . . .
H14A H 0.5021 0.6644 0.2599 0.110 Uiso 1 1 calc R U . . .
H14B H 0.5323 0.6697 0.1814 0.110 Uiso 1 1 calc R U . . .
C15 C 0.3159(7) 0.6570(4) 0.2035(4) 0.127(2) Uani 1 1 d . . . . .
H15A H 0.2981 0.7146 0.2010 0.152 Uiso 1 1 calc R U . . .
H15B H 0.2588 0.6355 0.2411 0.152 Uiso 1 1 calc R U . . .
C16 C 0.2669(7) 0.6171(4) 0.1371(4) 0.133(2) Uani 1 1 d . . . . .
H16A H 0.1616 0.6241 0.1316 0.160 Uiso 1 1 calc R U . . .
H16B H 0.3151 0.6435 0.0990 0.160 Uiso 1 1 calc R U . . .
C17 C 0.3023(8) 0.5299(4) 0.1360(5) 0.150(3) Uani 1 1 d . . . . .
H17A H 0.2448 0.5026 0.1706 0.180 Uiso 1 1 calc R U . . .
H17B H 0.2749 0.5076 0.0921 0.180 Uiso 1 1 calc R U . . .
C18 C 0.4603(6) 0.5145(3) 0.1483(3) 0.1072(16) Uani 1 1 d . . . . .
H18A H 0.5169 0.5360 0.1105 0.129 Uiso 1 1 calc R U . . .
H18B H 0.4770 0.4567 0.1501 0.129 Uiso 1 1 calc R U . . .
C19 C 0.9709(5) 0.3769(2) 0.16481(17) 0.0698(8) Uani 1 1 d D U . . .
C20 C 0.8389(10) 0.3742(8) 0.1298(4) 0.089(3) Uani 0.500(10) 1 d D U P A 1
H20 H 0.7506 0.3802 0.1532 0.107 Uiso 0.500(10) 1 calc R U P A 1
C21 C 0.8385(13) 0.3626(8) 0.0595(4) 0.094(2) Uani 0.500(10) 1 d D U P A 1
H21 H 0.7497 0.3645 0.0361 0.112 Uiso 0.500(10) 1 calc R U P A 1
C22 C 0.9664(14) 0.3483(8) 0.0238(3) 0.088(2) Uani 0.500(10) 1 d D U P A 1
C23 C 1.0946(12) 0.3421(10) 0.0607(4) 0.090(2) Uani 0.500(10) 1 d D U P A 1
H23 H 1.1811 0.3280 0.0383 0.108 Uiso 0.500(10) 1 calc R U P A 1
C24 C 1.0984(10) 0.3566(11) 0.1314(4) 0.082(3) Uani 0.500(10) 1 d D U P A 1
H24 H 1.1864 0.3524 0.1552 0.098 Uiso 0.500(10) 1 calc R U P A 1
C25 C 0.9637(12) 0.3384(6) -0.0535(3) 0.101(3) Uani 0.500(10) 1 d D U P A 1
H25 H 0.8638 0.3361 -0.0722 0.122 Uiso 0.500(10) 1 calc R U P A 1
C26 C 1.0624(18) 0.4149(7) -0.0849(7) 0.115(4) Uani 0.500(10) 1 d D U P A 1
H26A H 1.0742 0.4079 -0.1332 0.172 Uiso 0.500(10) 1 calc R U P A 1
H26B H 1.1574 0.4157 -0.0635 0.172 Uiso 0.500(10) 1 calc R U P A 1
H26C H 1.0126 0.4649 -0.0761 0.172 Uiso 0.500(10) 1 calc R U P A 1
C27 C 1.0580(19) 0.2689(7) -0.0761(7) 0.123(4) Uani 0.500(10) 1 d D U P A 1
H27A H 1.0515 0.2631 -0.1246 0.185 Uiso 0.500(10) 1 calc R U P A 1
H27B H 1.0244 0.2202 -0.0546 0.185 Uiso 0.500(10) 1 calc R U P A 1
H27C H 1.1583 0.2789 -0.0634 0.185 Uiso 0.500(10) 1 calc R U P A 1
C20A C 0.8665(11) 0.3953(7) 0.1171(4) 0.083(3) Uani 0.500(10) 1 d D U P A 2
H20A H 0.7780 0.4187 0.1304 0.100 Uiso 0.500(10) 1 calc R U P A 2
C21A C 0.8926(14) 0.3790(7) 0.0481(4) 0.091(2) Uani 0.500(10) 1 d D U P A 2
H21A H 0.8189 0.3891 0.0164 0.109 Uiso 0.500(10) 1 calc R U P A 2
C22A C 1.0250(15) 0.3484(8) 0.0263(3) 0.091(2) Uani 0.500(10) 1 d D U P A 2
C23A C 1.1285(12) 0.3292(9) 0.0751(4) 0.089(2) Uani 0.500(10) 1 d D U P A 2
H23A H 1.2176 0.3067 0.0616 0.106 Uiso 0.500(10) 1 calc R U P A 2
C24A C 1.1023(11) 0.3427(11) 0.1449(4) 0.081(3) Uani 0.500(10) 1 d D U P A 2
H24A H 1.1728 0.3288 0.1771 0.097 Uiso 0.500(10) 1 calc R U P A 2
C25A C 1.0559(13) 0.3365(6) -0.0497(3) 0.103(3) Uani 0.500(10) 1 d D U P A 2
H25A H 1.1606 0.3308 -0.0605 0.124 Uiso 0.500(10) 1 calc R U P A 2
C26A C 0.975(2) 0.4150(8) -0.0888(7) 0.140(5) Uani 0.500(10) 1 d D U P A 2
H26D H 0.9958 0.4127 -0.1368 0.209 Uiso 0.500(10) 1 calc R U P A 2
H26E H 1.0132 0.4645 -0.0704 0.209 Uiso 0.500(10) 1 calc R U P A 2
H26F H 0.8710 0.4127 -0.0817 0.209 Uiso 0.500(10) 1 calc R U P A 2
C27A C 0.961(2) 0.2695(8) -0.0784(7) 0.133(5) Uani 0.500(10) 1 d D U P A 2
H27D H 0.9794 0.2643 -0.1264 0.199 Uiso 0.500(10) 1 calc R U P A 2
H27E H 0.8595 0.2820 -0.0710 0.199 Uiso 0.500(10) 1 calc R U P A 2
H27F H 0.9850 0.2196 -0.0560 0.199 Uiso 0.500(10) 1 calc R U P A 2
C28 C 0.8981(4) 0.3124(2) 0.39945(16) 0.0593(8) Uani 1 1 d . . . . .
H28 H 0.9075 0.2593 0.3846 0.071 Uiso 1 1 calc R U . . .
C29 C 0.8300(4) 0.32214(18) 0.46708(16) 0.0570(7) Uani 1 1 d . . . . .
C30 C 0.8467(4) 0.26158(19) 0.51589(17) 0.0595(8) Uani 1 1 d . . . . .
H30 H 0.9049 0.2168 0.5062 0.071 Uiso 1 1 calc R U . . .
C31 C 0.7777(4) 0.26732(19) 0.57878(16) 0.0572(7) Uani 1 1 d . . . . .
C32 C 0.6884(4) 0.33390(18) 0.59275(16) 0.0549(7) Uani 1 1 d . . . . .
C33 C 0.6690(4) 0.39268(19) 0.54384(18) 0.0626(8) Uani 1 1 d . . . . .
H33 H 0.6081 0.4366 0.5528 0.075 Uiso 1 1 calc R U . . .
C34 C 0.7391(4) 0.3870(2) 0.48155(18) 0.0643(8) Uani 1 1 d . . . . .
H34 H 0.7251 0.4271 0.4490 0.077 Uiso 1 1 calc R U . . .
C35 C 0.8833(7) 0.1464(3) 0.6219(3) 0.115(2) Uani 1 1 d . . . . .
H35A H 0.8514 0.1150 0.5835 0.172 Uiso 1 1 calc R U . . .
H35B H 0.8815 0.1135 0.6621 0.172 Uiso 1 1 calc R U . . .
H35C H 0.9817 0.1653 0.6141 0.172 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 C3 1.230(4) . ?
O2 C11 1.212(4) . ?
O3 C32 1.363(4) . ?
O3 H3 0.838(14) . ?
O4 C31 1.362(4) . ?
O4 C35 1.408(5) . ?
C1 N2 1.466(4) . ?
C1 C9 1.511(5) . ?
C1 C11 1.538(5) . ?
C1 H1 0.9800 . ?
N2 C3 1.352(4) . ?
N2 C19 1.444(4) . ?
C3 C4 1.492(5) . ?
C4 C28 1.339(5) . ?
C4 C10 1.476(5) . ?
C5 C6 1.378(6) . ?
C5 C10 1.403(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.387(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(5) . ?
C11 N12 1.327(4) . ?
N12 C13 1.431(5) . ?
N12 H12 0.895(14) . ?
C13 C14 1.516(6) . ?
C13 C18 1.535(7) . ?
C13 H13 0.9800 . ?
C14 C15 1.490(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.528(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.479(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.479(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20A 1.369(8) . ?
C19 C24 1.374(9) . ?
C19 C24A 1.379(9) . ?
C19 C20 1.383(9) . ?
C20 C21 1.393(10) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(12) . ?
C21 H21 0.9300 . ?
C22 C23 1.377(11) . ?
C22 C25 1.527(8) . ?
C23 C24 1.409(9) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C27 1.502(12) . ?
C25 C26 1.670(12) . ?
C25 H25 0.9800 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C20A C21A 1.401(10) . ?
C20A H20A 0.9300 . ?
C21A C22A 1.375(12) . ?
C21A H21A 0.9300 . ?
C22A C23A 1.380(11) . ?
C22A C25A 1.531(9) . ?
C23A C24A 1.408(10) . ?
C23A H23A 0.9300 . ?
C24A H24A 0.9300 . ?
C25A C27A 1.513(12) . ?
C25A C26A 1.677(12) . ?
C25A H25A 0.9800 . ?
C26A H26D 0.9600 . ?
C26A H26E 0.9600 . ?
C26A H26F 0.9600 . ?
C27A H27D 0.9600 . ?
C27A H27E 0.9600 . ?
C27A H27F 0.9600 . ?
C28 C29 1.474(5) . ?
C28 H28 0.9300 . ?
C29 C34 1.384(5) . ?
C29 C30 1.395(4) . ?
C30 C31 1.388(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.397(5) . ?
C32 C33 1.379(5) . ?
C33 C34 1.382(5) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?

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
C32 O3 H3 104(3) . . ?
C31 O4 C35 118.2(3) . . ?
N2 C1 C9 111.2(3) . . ?
N2 C1 C11 111.2(3) . . ?
C9 C1 C11 109.5(3) . . ?
N2 C1 H1 108.3 . . ?
C9 C1 H1 108.3 . . ?
C11 C1 H1 108.3 . . ?
C3 N2 C19 120.5(3) . . ?
C3 N2 C1 122.0(3) . . ?
C19 N2 C1 116.1(3) . . ?
O1 C3 N2 120.8(3) . . ?
O1 C3 C4 123.0(3) . . ?
N2 C3 C4 116.2(3) . . ?
C28 C4 C10 126.9(3) . . ?
C28 C4 C3 116.7(3) . . ?
C10 C4 C3 116.3(3) . . ?
C6 C5 C10 120.1(4) . . ?
C6 C5 H5 120.0 . . ?
C10 C5 H5 120.0 . . ?
C5 C6 C7 120.7(4) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 119.5(4) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 120.4(4) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 C1 121.5(3) . . ?
C10 C9 C1 117.8(3) . . ?
C9 C10 C5 118.7(3) . . ?
C9 C10 C4 118.3(3) . . ?
C5 C10 C4 122.9(3) . . ?
O2 C11 N12 125.2(4) . . ?
O2 C11 C1 121.1(3) . . ?
N12 C11 C1 113.8(3) . . ?
C11 N12 C13 124.5(3) . . ?
C11 N12 H12 120(3) . . ?
C13 N12 H12 116(3) . . ?
N12 C13 C14 110.7(4) . . ?
N12 C13 C18 111.4(4) . . ?
C14 C13 C18 109.9(4) . . ?
N12 C13 H13 108.3 . . ?
C14 C13 H13 108.3 . . ?
C18 C13 H13 108.3 . . ?
C15 C14 C13 112.7(5) . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 110.6(5) . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 111.7(6) . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 C16 112.2(5) . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 C13 112.2(6) . . ?
C17 C18 H18A 109.2 . . ?
C13 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
C13 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C20A C19 C24A 119.9(5) . . ?
C24 C19 C20 119.1(5) . . ?
C20A C19 N2 124.1(5) . . ?
C24 C19 N2 125.3(5) . . ?
C24A C19 N2 115.7(5) . . ?
C20 C19 N2 115.5(5) . . ?
C19 C20 C21 119.9(7) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 121.7(8) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C23 C22 C21 117.4(6) . . ?
C23 C22 C25 121.9(8) . . ?
C21 C22 C25 120.7(9) . . ?
C22 C23 C24 121.7(7) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C19 C24 C23 119.4(7) . . ?
C19 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C27 C25 C22 111.5(7) . . ?
C27 C25 C26 99.5(8) . . ?
C22 C25 C26 106.0(6) . . ?
C27 C25 H25 112.9 . . ?
C22 C25 H25 112.9 . . ?
C26 C25 H25 112.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C19 C20A C21A 120.1(7) . . ?
C19 C20A H20A 120.0 . . ?
C21A C20A H20A 120.0 . . ?
C22A C21A C20A 121.4(7) . . ?
C22A C21A H21A 119.3 . . ?
C20A C21A H21A 119.3 . . ?
C21A C22A C23A 117.7(6) . . ?
C21A C22A C25A 120.8(8) . . ?
C23A C22A C25A 121.5(9) . . ?
C22A C23A C24A 121.6(7) . . ?
C22A C23A H23A 119.2 . . ?
C24A C23A H23A 119.2 . . ?
C19 C24A C23A 119.2(7) . . ?
C19 C24A H24A 120.4 . . ?
C23A C24A H24A 120.4 . . ?
C27A C25A C22A 110.6(7) . . ?
C27A C25A C26A 98.7(8) . . ?
C22A C25A C26A 105.4(6) . . ?
C27A C25A H25A 113.6 . . ?
C22A C25A H25A 113.6 . . ?
C26A C25A H25A 113.6 . . ?
C25A C26A H26D 109.5 . . ?
C25A C26A H26E 109.5 . . ?
H26D C26A H26E 109.5 . . ?
C25A C26A H26F 109.5 . . ?
H26D C26A H26F 109.5 . . ?
H26E C26A H26F 109.5 . . ?
C25A C27A H27D 109.5 . . ?
C25A C27A H27E 109.5 . . ?
H27D C27A H27E 109.5 . . ?
C25A C27A H27F 109.5 . . ?
H27D C27A H27F 109.5 . . ?
H27E C27A H27F 109.5 . . ?
C4 C28 C29 129.7(3) . . ?
C4 C28 H28 115.2 . . ?
C29 C28 H28 115.2 . . ?
C34 C29 C30 118.8(3) . . ?
C34 C29 C28 121.4(3) . . ?
C30 C29 C28 119.6(3) . . ?
C31 C30 C29 120.8(3) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
O4 C31 C30 125.8(3) . . ?
O4 C31 C32 114.8(3) . . ?
C30 C31 C32 119.5(3) . . ?
O3 C32 C33 118.9(3) . . ?
O3 C32 C31 121.4(3) . . ?
C33 C32 C31 119.7(3) . . ?
C32 C33 C34 120.6(3) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C33 C34 C29 120.7(3) . . ?
C33 C34 H34 119.7 . . ?
C29 C34 H34 119.7 . . ?
O4 C35 H35A 109.5 . . ?
O4 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O4 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 N2 C3 38.9(4) . . . . ?
C11 C1 N2 C3 -83.4(4) . . . . ?
C9 C1 N2 C19 -154.1(3) . . . . ?
C11 C1 N2 C19 83.6(4) . . . . ?
C19 N2 C3 O1 5.9(5) . . . . ?
C1 N2 C3 O1 172.3(3) . . . . ?
C19 N2 C3 C4 -173.6(3) . . . . ?
C1 N2 C3 C4 -7.2(5) . . . . ?
O1 C3 C4 C28 -29.5(5) . . . . ?
N2 C3 C4 C28 150.0(3) . . . . ?
O1 C3 C4 C10 152.5(3) . . . . ?
N2 C3 C4 C10 -28.0(5) . . . . ?
C10 C5 C6 C7 -0.2(8) . . . . ?
C5 C6 C7 C8 -1.4(8) . . . . ?
C6 C7 C8 C9 0.7(8) . . . . ?
C7 C8 C9 C10 1.7(7) . . . . ?
C7 C8 C9 C1 177.6(4) . . . . ?
N2 C1 C9 C8 147.4(4) . . . . ?
C11 C1 C9 C8 -89.3(4) . . . . ?
N2 C1 C9 C10 -36.5(4) . . . . ?
C11 C1 C9 C10 86.8(4) . . . . ?
C8 C9 C10 C5 -3.3(6) . . . . ?
C1 C9 C10 C5 -179.4(4) . . . . ?
C8 C9 C10 C4 -179.8(4) . . . . ?
C1 C9 C10 C4 4.1(5) . . . . ?
C6 C5 C10 C9 2.6(6) . . . . ?
C6 C5 C10 C4 178.9(4) . . . . ?
C28 C4 C10 C9 -148.5(4) . . . . ?
C3 C4 C10 C9 29.2(5) . . . . ?
C28 C4 C10 C5 35.1(6) . . . . ?
C3 C4 C10 C5 -147.2(4) . . . . ?
N2 C1 C11 O2 39.2(5) . . . . ?
C9 C1 C11 O2 -84.0(4) . . . . ?
N2 C1 C11 N12 -141.4(3) . . . . ?
C9 C1 C11 N12 95.4(4) . . . . ?
O2 C11 N12 C13 -3.9(7) . . . . ?
C1 C11 N12 C13 176.7(4) . . . . ?
C11 N12 C13 C14 152.2(4) . . . . ?
C11 N12 C13 C18 -85.2(5) . . . . ?
N12 C13 C14 C15 177.1(4) . . . . ?
C18 C13 C14 C15 53.7(6) . . . . ?
C13 C14 C15 C16 -54.6(7) . . . . ?
C14 C15 C16 C17 54.7(8) . . . . ?
C15 C16 C17 C18 -55.4(10) . . . . ?
C16 C17 C18 C13 55.1(10) . . . . ?
N12 C13 C18 C17 -176.3(5) . . . . ?
C14 C13 C18 C17 -53.3(7) . . . . ?
C3 N2 C19 C20A 127.8(7) . . . . ?
C1 N2 C19 C20A -39.4(8) . . . . ?
C3 N2 C19 C24 -71.6(11) . . . . ?
C1 N2 C19 C24 121.3(11) . . . . ?
C3 N2 C19 C24A -58.7(10) . . . . ?
C1 N2 C19 C24A 134.2(9) . . . . ?
C3 N2 C19 C20 105.8(8) . . . . ?
C1 N2 C19 C20 -61.3(8) . . . . ?
C24 C19 C20 C21 -9.3(16) . . . . ?
N2 C19 C20 C21 173.1(9) . . . . ?
C19 C20 C21 C22 4.3(18) . . . . ?
C20 C21 C22 C23 3.0(19) . . . . ?
C20 C21 C22 C25 -178.1(11) . . . . ?
C21 C22 C23 C24 -5(2) . . . . ?
C25 C22 C23 C24 175.7(13) . . . . ?
C20 C19 C24 C23 7.0(19) . . . . ?
N2 C19 C24 C23 -175.7(10) . . . . ?
C22 C23 C24 C19 0(2) . . . . ?
C23 C22 C25 C27 42.8(16) . . . . ?
C21 C22 C25 C27 -136.0(13) . . . . ?
C23 C22 C25 C26 -64.5(15) . . . . ?
C21 C22 C25 C26 116.6(13) . . . . ?
C24A C19 C20A C21A 0.4(15) . . . . ?
N2 C19 C20A C21A 173.7(7) . . . . ?
C19 C20A C21A C22A -3.4(16) . . . . ?
C20A C21A C22A C23A 4.2(18) . . . . ?
C20A C21A C22A C25A -175.6(10) . . . . ?
C21A C22A C23A C24A -2(2) . . . . ?
C25A C22A C23A C24A 177.7(13) . . . . ?
C20A C19 C24A C23A 1.6(19) . . . . ?
N2 C19 C24A C23A -172.3(11) . . . . ?
C22A C23A C24A C19 -1(2) . . . . ?
C21A C22A C25A C27A -68.8(14) . . . . ?
C23A C22A C25A C27A 111.5(15) . . . . ?
C21A C22A C25A C26A 37.0(15) . . . . ?
C23A C22A C25A C26A -142.8(15) . . . . ?
C10 C4 C28 C29 12.3(6) . . . . ?
C3 C4 C28 C29 -165.4(3) . . . . ?
C4 C28 C29 C34 35.3(6) . . . . ?
C4 C28 C29 C30 -150.3(4) . . . . ?
C34 C29 C30 C31 -2.2(5) . . . . ?
C28 C29 C30 C31 -176.7(3) . . . . ?
C35 O4 C31 C30 3.4(6) . . . . ?
C35 O4 C31 C32 -176.4(4) . . . . ?
C29 C30 C31 O4 -178.6(3) . . . . ?
C29 C30 C31 C32 1.1(5) . . . . ?
O4 C31 C32 O3 3.0(4) . . . . ?
C30 C31 C32 O3 -176.7(3) . . . . ?
O4 C31 C32 C33 -179.7(3) . . . . ?
C30 C31 C32 C33 0.5(5) . . . . ?
O3 C32 C33 C34 176.2(3) . . . . ?
C31 C32 C33 C34 -1.1(5) . . . . ?
C32 C33 C34 C29 0.1(5) . . . . ?
C30 C29 C34 C33 1.6(5) . . . . ?
C28 C29 C34 C33 176.0(3) . . . . ?

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
O3 H3 O1 0.838(14) 1.87(3) 2.623(3) 148(4) 2_456
O3 H3 O4 0.838(14) 2.26(4) 2.679(4) 111(3) .
C1 H1 O3 0.98 2.65 3.497(4) 144.3 4_664
N12 H12 O3 0.895(14) 2.12(2) 2.987(4) 162(4) 4_664

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM-MeOH'
