# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_LA88
_database_code_depnum_ccdc_archive 'CCDC 2253860'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H34 N2 O6, 2(C3 H6 O)'
_chemical_formula_sum            'C44 H46 N2 O8'
_chemical_formula_weight         730.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.9695(4)
_cell_length_b                   10.9993(5)
_cell_length_c                   11.5562(5)
_cell_angle_alpha                62.1699(10)
_cell_angle_beta                 79.6611(10)
_cell_angle_gamma                79.0306(10)
_cell_volume                     984.41(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7989
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      33.09
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8335
_exptl_absorpt_correction_T_max  0.8751
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-Ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            24408
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.813
_diffrn_reflns_theta_max         29.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5739
_reflns_number_gt                4550
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    
;
SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_computing_structure_refinement  
;
SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)
;
_computing_molecular_graphics    'SHELXTL (Bruker, 2018)'
_computing_publication_material  'SHELXTL (Bruker, 2018)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.3917P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5739
_refine_ls_number_parameters     260
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1208
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.45142(12) 0.46405(11) 0.49648(11) 0.0136(2) Uani 1 1 d . . . . .
H1 H 0.351727 0.467248 0.540665 0.016 Uiso 1 1 calc R U . . .
C2 C 0.48744(12) 0.37686(11) 0.42309(10) 0.0127(2) Uani 1 1 d . . . . .
C3 C 0.41909(12) 0.24057(11) 0.50097(11) 0.0144(2) Uani 1 1 d . . . . .
C4 C 0.41376(13) 0.17154(12) 0.63750(12) 0.0185(2) Uani 1 1 d . . . . .
H4 H 0.451264 0.210320 0.683182 0.022 Uiso 1 1 calc R U . . .
C5 C 0.35373(15) 0.04592(13) 0.70738(13) 0.0243(3) Uani 1 1 d . . . . .
H5 H 0.350954 -0.000990 0.800546 0.029 Uiso 1 1 calc R U . . .
C6 C 0.29785(14) -0.01112(13) 0.64143(14) 0.0255(3) Uani 1 1 d . . . . .
H6 H 0.256406 -0.096653 0.689226 0.031 Uiso 1 1 calc R U . . .
C7 C 0.30288(14) 0.05712(13) 0.50620(14) 0.0239(3) Uani 1 1 d . . . . .
H7 H 0.264664 0.018325 0.460883 0.029 Uiso 1 1 calc R U . . .
C8 C 0.36338(13) 0.18213(12) 0.43568(13) 0.0185(2) Uani 1 1 d . . . . .
H8 H 0.366825 0.228046 0.342463 0.022 Uiso 1 1 calc R U . . .
C9 C 0.65811(12) 0.35125(11) 0.38296(11) 0.0134(2) Uani 1 1 d . . . . .
C10 C 0.75453(13) 0.26391(12) 0.47975(12) 0.0165(2) Uani 1 1 d . . . . .
H10 H 0.713813 0.222738 0.569495 0.020 Uiso 1 1 calc R U . . .
C11 C 0.90974(13) 0.23667(13) 0.44590(12) 0.0190(2) Uani 1 1 d . . . . .
H11 H 0.974339 0.177242 0.512569 0.023 Uiso 1 1 calc R U . . .
C12 C 0.97042(13) 0.29583(13) 0.31542(13) 0.0206(2) Uani 1 1 d . . . . .
H12 H 1.076074 0.275968 0.292185 0.025 Uiso 1 1 calc R U . . .
C13 C 0.87603(14) 0.38407(14) 0.21918(13) 0.0220(3) Uani 1 1 d . . . . .
H13 H 0.917314 0.425267 0.129591 0.026 Uiso 1 1 calc R U . . .
C14 C 0.72062(13) 0.41302(13) 0.25270(12) 0.0177(2) Uani 1 1 d . . . . .
H14 H 0.657207 0.475335 0.186045 0.021 Uiso 1 1 calc R U . . .
O1 O 0.42063(9) 0.45417(8) 0.29820(8) 0.01473(17) Uani 1 1 d . . . . .
N1 N 0.26932(10) 0.50806(10) 0.31813(10) 0.01539(19) Uani 1 1 d . . . . .
C15 C 0.20788(13) 0.56273(12) 0.21033(11) 0.0159(2) Uani 1 1 d . . . . .
C16 C 0.28675(13) 0.55727(13) 0.08510(11) 0.0187(2) Uani 1 1 d . . . . .
O2 O 0.28026(12) 0.45698(10) 0.06984(9) 0.0267(2) Uani 1 1 d . . . . .
C17 C 0.36649(16) 0.67823(15) -0.01056(13) 0.0281(3) Uani 1 1 d . . . . .
H17A H 0.446310 0.688326 0.031092 0.042 Uiso 1 1 calc R U . . .
H17B H 0.292911 0.762309 -0.038431 0.042 Uiso 1 1 calc R U . . .
H17C H 0.412822 0.663826 -0.087405 0.042 Uiso 1 1 calc R U . . .
C18 C 0.05047(13) 0.63783(13) 0.20645(12) 0.0206(2) Uani 1 1 d . . . . .
O3 O -0.00022(11) 0.69977(11) 0.10031(10) 0.0331(2) Uani 1 1 d . . . . .
C19 C -0.03597(14) 0.63268(15) 0.33081(14) 0.0262(3) Uani 1 1 d . . . . .
H19A H 0.028693 0.653988 0.377262 0.039 Uiso 1 1 calc R U . . .
H19B H -0.066191 0.539804 0.386571 0.039 Uiso 1 1 calc R U . . .
H19C H -0.127380 0.700859 0.310573 0.039 Uiso 1 1 calc R U . . .
C21 C 0.23208(18) -0.00018(17) 0.12091(16) 0.0349(3) Uani 1 1 d D . . . .
O4A O 0.2965(2) -0.1168(2) 0.1387(3) 0.0532(6) Uani 0.794(5) 1 d D . P A 1
C20A C 0.0737(3) 0.0184(6) 0.1814(4) 0.0395(9) Uani 0.794(5) 1 d D . P A 1
H20A H 0.076044 0.042786 0.252466 0.059 Uiso 0.794(5) 1 calc R U P A 1
H20B H 0.028333 -0.068047 0.217174 0.059 Uiso 0.794(5) 1 calc R U P A 1
H20C H 0.012363 0.092714 0.114462 0.059 Uiso 0.794(5) 1 calc R U P A 1
C22A C 0.3135(8) 0.1250(5) 0.0540(8) 0.0458(11) Uani 0.794(5) 1 d D . P A 1
H22A H 0.259285 0.196001 -0.020109 0.069 Uiso 0.794(5) 1 calc R U P A 1
H22B H 0.417749 0.100516 0.021657 0.069 Uiso 0.794(5) 1 calc R U P A 1
H22C H 0.316971 0.161092 0.116560 0.069 Uiso 0.794(5) 1 calc R U P A 1
O4B O 0.2643(10) -0.0795(9) 0.0728(11) 0.0532(6) Uani 0.206(5) 1 d D . P A 2
C20B C 0.0631(9) 0.015(3) 0.1550(19) 0.0395(9) Uani 0.206(5) 1 d D . P A 2
H20D H 0.031085 0.101123 0.163880 0.059 Uiso 0.206(5) 1 calc R U P A 2
H20E H 0.035359 -0.063816 0.238367 0.059 Uiso 0.206(5) 1 calc R U P A 2
H20F H 0.011908 0.018744 0.085231 0.059 Uiso 0.206(5) 1 calc R U P A 2
C22B C 0.327(4) 0.115(2) 0.074(4) 0.0458(11) Uani 0.206(5) 1 d D . P A 2
H22D H 0.262011 0.204020 0.036430 0.069 Uiso 0.206(5) 1 calc R U P A 2
H22E H 0.407837 0.109163 0.007463 0.069 Uiso 0.206(5) 1 calc R U P A 2
H22F H 0.372056 0.107697 0.148824 0.069 Uiso 0.206(5) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C1 1.319(2) 2_666 ?
C1 C2 1.5121(15) . ?
C1 H1 0.9500 . ?
C2 O1 1.4614(13) . ?
C2 C3 1.5249(15) . ?
C2 C9 1.5301(15) . ?
C3 C4 1.3915(16) . ?
C3 C8 1.3937(16) . ?
C4 C5 1.3915(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3886(17) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.3889(16) . ?
C9 C10 1.3963(15) . ?
C10 C11 1.3915(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.3846(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3832(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3954(16) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
O1 N1 1.3984(11) . ?
N1 C15 1.2798(15) . ?
C15 C18 1.4907(16) . ?
C15 C16 1.5152(17) . ?
C16 O2 1.2089(16) . ?
C16 C17 1.4862(18) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 O3 1.2154(15) . ?
C18 C19 1.4868(18) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 O4B 1.205(6) . ?
C21 O4A 1.239(2) . ?
C21 C22A 1.488(3) . ?
C21 C20A 1.489(3) . ?
C21 C22B 1.491(8) . ?
C21 C20B 1.494(8) . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C22A H22A 0.9800 . ?
C22A H22B 0.9800 . ?
C22A H22C 0.9800 . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?

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
C1 C1 C2 124.65(13) 2_666 . ?
C1 C1 H1 117.7 2_666 . ?
C2 C1 H1 117.7 . . ?
O1 C2 C1 108.29(8) . . ?
O1 C2 C3 108.45(8) . . ?
C1 C2 C3 111.16(9) . . ?
O1 C2 C9 104.21(8) . . ?
C1 C2 C9 113.45(9) . . ?
C3 C2 C9 110.92(9) . . ?
C4 C3 C8 119.04(11) . . ?
C4 C3 C2 120.76(10) . . ?
C8 C3 C2 120.19(10) . . ?
C3 C4 C5 120.27(12) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.24(12) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 119.60(12) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 120.51(12) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C3 120.34(12) . . ?
C7 C8 H8 119.8 . . ?
C3 C8 H8 119.8 . . ?
C14 C9 C10 118.77(10) . . ?
C14 C9 C2 121.92(10) . . ?
C10 C9 C2 119.31(10) . . ?
C11 C10 C9 120.57(11) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 120.27(11) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 119.49(11) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.49(11) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 120.37(11) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
N1 O1 C2 110.53(8) . . ?
C15 N1 O1 109.61(9) . . ?
N1 C15 C18 118.48(11) . . ?
N1 C15 C16 123.76(10) . . ?
C18 C15 C16 117.76(10) . . ?
O2 C16 C17 125.00(12) . . ?
O2 C16 C15 118.55(11) . . ?
C17 C16 C15 116.44(11) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 C19 123.66(12) . . ?
O3 C18 C15 117.35(12) . . ?
C19 C18 C15 118.99(11) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4A C21 C22A 122.4(4) . . ?
O4A C21 C20A 121.0(3) . . ?
C22A C21 C20A 116.1(5) . . ?
O4B C21 C22B 118.4(19) . . ?
O4B C21 C20B 108.7(10) . . ?
C22B C21 C20B 123.3(19) . . ?
C21 C20A H20A 109.5 . . ?
C21 C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C21 C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C21 C22A H22A 109.5 . . ?
C21 C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C21 C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C21 C20B H20D 109.5 . . ?
C21 C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C21 C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C21 C22B H22D 109.5 . . ?
C21 C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C21 C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 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
C1 C1 C2 O1 -101.78(15) 2_666 . . . ?
C1 C1 C2 C3 139.19(14) 2_666 . . . ?
C1 C1 C2 C9 13.38(19) 2_666 . . . ?
O1 C2 C3 C4 -155.26(10) . . . . ?
C1 C2 C3 C4 -36.32(13) . . . . ?
C9 C2 C3 C4 90.89(12) . . . . ?
O1 C2 C3 C8 25.89(13) . . . . ?
C1 C2 C3 C8 144.83(10) . . . . ?
C9 C2 C3 C8 -87.96(12) . . . . ?
C8 C3 C4 C5 0.07(17) . . . . ?
C2 C3 C4 C5 -178.80(10) . . . . ?
C3 C4 C5 C6 -0.37(18) . . . . ?
C4 C5 C6 C7 0.32(18) . . . . ?
C5 C6 C7 C8 0.04(18) . . . . ?
C6 C7 C8 C3 -0.35(18) . . . . ?
C4 C3 C8 C7 0.29(16) . . . . ?
C2 C3 C8 C7 179.16(10) . . . . ?
O1 C2 C9 C14 8.42(14) . . . . ?
C1 C2 C9 C14 -109.14(12) . . . . ?
C3 C2 C9 C14 124.92(11) . . . . ?
O1 C2 C9 C10 -171.92(10) . . . . ?
C1 C2 C9 C10 70.51(13) . . . . ?
C3 C2 C9 C10 -55.42(13) . . . . ?
C14 C9 C10 C11 -1.54(17) . . . . ?
C2 C9 C10 C11 178.79(10) . . . . ?
C9 C10 C11 C12 -0.13(18) . . . . ?
C10 C11 C12 C13 1.08(19) . . . . ?
C11 C12 C13 C14 -0.34(19) . . . . ?
C10 C9 C14 C13 2.28(17) . . . . ?
C2 C9 C14 C13 -178.07(11) . . . . ?
C12 C13 C14 C9 -1.36(19) . . . . ?
C1 C2 O1 N1 -47.57(11) . . . . ?
C3 C2 O1 N1 73.16(10) . . . . ?
C9 C2 O1 N1 -168.63(8) . . . . ?
C2 O1 N1 C15 -173.26(9) . . . . ?
O1 N1 C15 C18 -174.59(9) . . . . ?
O1 N1 C15 C16 4.61(15) . . . . ?
N1 C15 C16 O2 85.38(15) . . . . ?
C18 C15 C16 O2 -95.43(14) . . . . ?
N1 C15 C16 C17 -94.86(15) . . . . ?
C18 C15 C16 C17 84.33(14) . . . . ?
N1 C15 C18 O3 173.35(12) . . . . ?
C16 C15 C18 O3 -5.89(17) . . . . ?
N1 C15 C18 C19 -7.02(17) . . . . ?
C16 C15 C18 C19 173.74(11) . . . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_b699-1
_database_code_depnum_ccdc_archive 'CCDC 2253892'
loop_
_audit_author_name
_audit_author_address
'Egor Igorevich Tuzharov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-09-01 downloaded from the CCDC.
;
_audit_creation_date             2021-12-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 N2 O6'
_chemical_formula_sum            'C24 H24 N2 O6'
_chemical_formula_weight         436.45
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     B.699-1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.2566(2)
_cell_length_b                   5.41860(10)
_cell_length_c                   18.4668(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.9970(10)
_cell_angle_gamma                90
_cell_volume                     1124.84(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8909
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.7980
_cell_measurement_theta_min      3.9040
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.886
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12674
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.466
_diffrn_reflns_theta_min         3.932
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    104.00 130.00   0.50    0.23    --  111.50  30.00  60.00   52
  2  ω    107.00 138.00   0.50    0.23    --  111.50  45.00 -30.00   62
  3  ω     96.00 178.00   0.50    0.23    --  111.50  61.00 -60.00  164
  4  ω    102.00 128.00   0.50    0.23    --  111.50  45.00-150.00   52
  5  ω    124.00 164.00   0.50    0.23    --  111.50  15.00-120.00   80
  6  ω    101.00 178.00   0.50    0.23    --  111.50  30.00 -90.00  154
  7  ω     68.00 178.00   0.50    0.23    --  111.50   4.00  42.00  220
  8  ω    145.00 178.00   0.50    0.23    --  111.50  30.00  60.00   66
  9  ω    110.00 136.00   0.50    0.23    --  111.50  30.00 120.00   52
 10  ω      5.00 120.00   0.50    0.06    --   48.51   4.00  42.00  230
 11  ω    -44.00  23.00   0.50    0.06    --  -48.51   4.00  42.00  134
 12  ω    -44.00 -18.00   0.50    0.23    --  -90.00   4.00  42.00   52
 13  ω    -51.00 -18.00   0.50    0.23    --  -90.00  45.00 -30.00   66
 14  ω    -26.00  26.00   0.50    0.06    --  -48.51  19.00-120.00  104
 15  ω   -120.00 -31.00   0.50    0.06    --  -48.51  -4.00-135.00  178
 16  ω   -162.00 -72.00   0.50    0.23    --  -90.00  -4.00-135.00  180
 17  ω    131.00 165.00   0.50    0.23    --  111.50 125.00 -60.00   68
 18  ω     40.00  66.00   0.50    0.23    --  111.50 -61.00  30.00   52
 19  ω     41.00  66.00   0.50    0.23    --  111.50 -61.00 -30.00   50
 20  ω    -23.00  63.00   0.50    0.06    --   48.51 -57.00-180.00  172
 21  ω     43.00  69.00   0.50    0.23    --  111.50 -61.00-150.00   52
 22  ω     60.00  86.00   0.50    0.23    --  111.50 -77.00-120.00   52
 23  ω     41.00  97.00   0.50    0.23    --  111.50 -77.00 -90.00  112
 24  ω     40.00 114.00   0.50    0.23    --  111.50-129.00 -10.28  148
 25  ω     78.00 104.00   0.50    0.23    --  111.50 -95.00  90.00   52
 26  ω     40.00 105.00   0.50    0.23    --  111.50 -95.00 120.00  130
 27  ω     55.00  81.00   0.50    0.23    --  111.50 -86.00 -48.96   52
 28  ω     64.00 109.00   0.50    0.23    --  111.50-125.00 -60.00   90
 29  ω     40.00 111.00   0.50    0.23    --  111.50-125.00-120.00  142
 30  ω     40.00 105.00   0.50    0.23    --  111.50 -95.00-180.00  130
 31  ω     47.00  73.00   0.50    0.23    --  111.50 -95.00-150.00   52
 32  ω     85.00 111.00   0.50    0.23    --  111.50 -86.00 -48.96   52
 33  ω     55.00  81.00   0.50    0.23    --  111.50 -81.00 142.57   52
 34  ω     40.00 136.00   0.50    0.23    --  111.50 -82.00 147.63  192
 35  ω    108.00 135.00   0.50    0.23    --  111.50 -81.00 142.57   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1078615000
_diffrn_orient_matrix_UB_12      0.0092898000
_diffrn_orient_matrix_UB_13      0.0479577000
_diffrn_orient_matrix_UB_21      -0.0846250000
_diffrn_orient_matrix_UB_22      -0.0097497000
_diffrn_orient_matrix_UB_23      -0.0682257000
_diffrn_orient_matrix_UB_31      -0.0006361000
_diffrn_orient_matrix_UB_32      -0.2840576000
_diffrn_orient_matrix_UB_33      0.0039242000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2227
_reflns_number_total             2420
_reflns_odcompleteness_completeness 95.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     86.18
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0045(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2420
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.100
_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)+(0.0585P)²+0.4312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1223
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C9(H9), C11(H11), C10(H10)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.37545(8) 0.66443(18) 0.45992(5) 0.0296(3) Uani 1 1 d . . . . .
O1 O 0.00370(9) 0.7881(2) 0.36120(6) 0.0433(3) Uani 1 1 d . . . . .
O2 O 0.18641(11) 1.1155(2) 0.46374(7) 0.0453(3) Uani 1 1 d . . . . .
N1 N 0.29168(10) 0.6007(2) 0.40469(6) 0.0284(3) Uani 1 1 d . . . . .
C7 C 0.54349(11) 0.4822(3) 0.39905(7) 0.0269(3) Uani 1 1 d . . . . .
C3 C 0.19453(11) 0.7190(2) 0.41192(7) 0.0266(3) Uani 1 1 d . . . . .
C4 C 0.17347(11) 0.8975(3) 0.47312(8) 0.0302(3) Uani 1 1 d . . . . .
C2 C 0.09357(12) 0.6655(3) 0.35828(7) 0.0307(3) Uani 1 1 d . . . . .
C6 C 0.46670(11) 0.4741(3) 0.46376(7) 0.0274(3) Uani 1 1 d . . . . .
H6 H 0.427703 0.308624 0.465878 0.033 Uiso 1 1 calc R U . . .
C8 C 0.62442(12) 0.6726(3) 0.38958(7) 0.0309(3) Uani 1 1 d . . . . .
H8 H 0.631367 0.802881 0.423949 0.037 Uiso 1 1 calc R U . . .
C12 C 0.53303(12) 0.2950(3) 0.34762(8) 0.0307(3) Uani 1 1 d . . . . .
H12 H 0.477947 0.164709 0.353623 0.037 Uiso 1 1 calc R U . . .
C9 C 0.69509(13) 0.6726(3) 0.33003(8) 0.0341(3) Uani 1 1 d . . . . .
H9 H 0.751091 0.801291 0.324223 0.041 Uiso 1 1 calc R U . . .
C11 C 0.60246(13) 0.2967(3) 0.28744(8) 0.0342(3) Uani 1 1 d . . . . .
H11 H 0.594000 0.169215 0.252225 0.041 Uiso 1 1 calc R U . . .
C10 C 0.68385(13) 0.4845(3) 0.27905(8) 0.0335(3) Uani 1 1 d . . . . .
H10 H 0.732105 0.484846 0.238359 0.040 Uiso 1 1 calc R U . . .
C5 C 0.13528(15) 0.7846(3) 0.54164(8) 0.0417(4) Uani 1 1 d . . . . .
H5A H 0.124521 0.914451 0.577664 0.063 Uiso 1 1 calc R U . . .
H5B H 0.196226 0.668352 0.560194 0.063 Uiso 1 1 calc R U . . .
H5C H 0.059970 0.696790 0.532167 0.063 Uiso 1 1 calc R U . . .
C1 C 0.10660(15) 0.4611(3) 0.30529(9) 0.0422(4) Uani 1 1 d . . . . .
H1A H 0.101848 0.302228 0.330343 0.063 Uiso 1 1 calc R U . . .
H1B H 0.183784 0.474961 0.283423 0.063 Uiso 1 1 calc R U . . .
H1C H 0.042723 0.471639 0.267274 0.063 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 N1 1.3957(14) . ?
O3 C6 1.4547(16) . ?
O1 C2 1.2137(17) . ?
O2 C4 1.2034(19) . ?
N1 C3 1.2806(17) . ?
C7 C6 1.5117(18) . ?
C7 C8 1.3931(19) . ?
C7 C12 1.390(2) . ?
C3 C4 1.5158(19) . ?
C3 C2 1.4963(18) . ?
C4 C5 1.489(2) . ?
C2 C1 1.490(2) . ?
C6 C6 1.525(3) 3_666 ?
C6 H6 1.0000 . ?
C8 H8 0.9500 . ?
C8 C9 1.390(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.392(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.383(2) . ?
C10 H10 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O3 C6 107.97(9) . . ?
C3 N1 O3 110.36(11) . . ?
C8 C7 C6 121.71(12) . . ?
C12 C7 C6 119.15(12) . . ?
C12 C7 C8 119.13(12) . . ?
N1 C3 C4 124.40(12) . . ?
N1 C3 C2 117.21(12) . . ?
C2 C3 C4 118.31(11) . . ?
O2 C4 C3 119.61(13) . . ?
O2 C4 C5 124.62(14) . . ?
C5 C4 C3 115.77(13) . . ?
O1 C2 C3 118.07(13) . . ?
O1 C2 C1 123.14(13) . . ?
C1 C2 C3 118.76(12) . . ?
O3 C6 C7 111.85(10) . . ?
O3 C6 C6 103.05(13) . 3_666 ?
O3 C6 H6 109.1 . . ?
C7 C6 C6 114.39(13) . 3_666 ?
C7 C6 H6 109.1 . . ?
C6 C6 H6 109.1 3_666 . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.28(13) . . ?
C9 C8 H8 119.9 . . ?
C7 C12 H12 119.7 . . ?
C7 C12 C11 120.65(13) . . ?
C11 C12 H12 119.7 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.03(13) . . ?
C10 C9 H9 120.0 . . ?
C12 C11 H11 120.1 . . ?
C10 C11 C12 119.80(13) . . ?
C10 C11 H11 120.1 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.09(13) . . ?
C11 C10 H10 120.0 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
O3 N1 C3 C4 -1.47(18) . . . . ?
O3 N1 C3 C2 -178.02(11) . . . . ?
N1 O3 C6 C7 70.63(13) . . . . ?
N1 O3 C6 C6 -166.02(12) . . . 3_666 ?
N1 C3 C4 O2 96.94(17) . . . . ?
N1 C3 C4 C5 -84.07(17) . . . . ?
N1 C3 C2 O1 -174.97(13) . . . . ?
N1 C3 C2 C1 6.6(2) . . . . ?
C7 C8 C9 C10 1.0(2) . . . . ?
C7 C12 C11 C10 0.8(2) . . . . ?
C4 C3 C2 O1 8.3(2) . . . . ?
C4 C3 C2 C1 -170.13(13) . . . . ?
C2 C3 C4 O2 -86.54(17) . . . . ?
C2 C3 C4 C5 92.45(15) . . . . ?
C6 O3 N1 C3 161.80(11) . . . . ?
C6 C7 C8 C9 178.99(12) . . . . ?
C6 C7 C12 C11 -179.93(12) . . . . ?
C8 C7 C6 O3 70.63(15) . . . . ?
C8 C7 C6 C6 -46.0(2) . . . 3_666 ?
C8 C7 C12 C11 0.1(2) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C12 C7 C6 O3 -109.32(13) . . . . ?
C12 C7 C6 C6 134.00(15) . . . 3_666 ?
C12 C7 C8 C9 -1.1(2) . . . . ?
C12 C11 C10 C9 -0.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.587
_oxdiff_exptl_absorpt_empirical_full_min 0.582
####################################################################### 
# 
# 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_la-293
_database_code_depnum_ccdc_archive 'CCDC 2253861'
loop_
_audit_author_name
_audit_author_address
'Roman Alekseevich Dolotov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-09-01 downloaded from the CCDC.
;
_audit_creation_date             2022-11-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 N2 O5'
_chemical_formula_sum            'C24 H22 N2 O5'
_chemical_formula_weight         418.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.6766(3)
_cell_length_b                   15.1780(4)
_cell_length_c                   12.1389(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.950(2)
_cell_angle_gamma                90
_cell_volume                     2078.53(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15408
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      77.4360
_cell_measurement_theta_min      3.7450
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 -1 0.0340
1 -1 1 0.0773
1 1 1 0.0217
-1 -1 -1 0.0324
0 -1 1 0.0748
1 0 -1 0.0248
-1 0 1 0.0095
0 -1 0 0.0650
0 1 0 0.0512

_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1019
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25662
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.826
_diffrn_reflns_theta_min         4.686
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00   0.00   0.50    4.11    --  -48.70 103.00 121.00  162
  2  ω     31.00  57.00   0.50    4.11    --   48.70-103.00  18.00   52
  3  ω    -73.00 -48.00   0.50   17.87    --  -86.25 103.00 121.00   50
  4  ω   -120.00 -91.00   0.50   17.87    --  -86.25-103.00  18.00   58
  5  ω     64.00  90.00   0.50   17.87    --  107.75-103.00  18.00   52
  6  ω    135.00 161.00   0.50   17.87    --  107.75 103.00 121.00   52
  7  ω   -116.00 -74.00   0.50    4.11    --  -48.70-125.00 -60.00   84
  8  ω   -115.00 -74.00   0.50    4.11    --  -48.70-125.00-180.00   82
  9  ω    -26.00  25.00   0.50    4.11    --  -48.70  19.00  30.00  102
 10  ω   -107.00 -74.00   0.50    4.11    --  -48.70-125.00 150.00   66
 11  ω   -115.00 -74.00   0.50    4.11    --  -48.70-125.00 120.00   82
 12  ω     77.00 103.00   0.50   17.87    --  107.75 -95.00  30.00   52
 13  ω     76.00 101.00   0.50   17.87    --  107.75-107.00 132.60   50
 14  ω     36.00  61.00   0.50   17.87    --  107.75 -54.00  -3.08   50
 15  ω    116.00 158.00   0.50   17.87    --  107.75  77.00-180.00   84
 16  ω     38.00  65.00   0.50   17.87    --  107.75 -61.00 120.00   54
 17  ω     44.00 105.00   0.50   17.87    --  107.75 -77.00  90.00  122
 18  ω     36.00  70.00   0.50   17.87    --  107.75 -95.00  30.00   68
 19  ω     54.00  79.00   0.50   17.87    --  107.75-144.00  13.18   50
 20  ω     99.00 165.00   0.50   17.87    --  107.75  15.00-180.00  132
 21  ω     37.00  70.00   0.50   17.87    --  107.75 -61.00 -90.00   66
 22  ω    105.00 177.00   0.50   17.87    --  107.75  45.00   0.00  144
 23  ω     38.00  90.00   0.50   17.87    --  107.75 -77.00  30.00  104
 24  ω     39.00  71.00   0.50   17.87    --  107.75 -61.00 -60.00   64
 25  ω     49.00  78.00   0.50   17.87    --  107.75-125.00 120.00   58
 26  ω     86.00 111.00   0.50   17.87    --  107.75-125.00 120.00   50
 27  ω    135.00 163.00   0.50   17.87    --  107.75   0.00-180.00   56
 28  ω     93.00 139.00   0.50   17.87    --  107.75  61.00-150.00   92
 29  ω     38.00  63.00   0.50   17.87    --  107.75 -77.00   0.00   50
 30  ω     67.00  94.00   0.50   17.87    --  107.75 -77.00   0.00   54
 31  ω     58.00 108.00   0.50   17.87    --  107.75-107.00-138.08  100
 32  ω     63.00  97.00   0.50   17.87    --  107.75 -77.00  54.21   68
 33  ω     36.00  80.00   0.50   17.87    --  107.75   0.00-180.00   88
 34  ω     94.00 125.00   0.50   17.87    --  107.75-144.00  13.18   62
 35  ω    104.00 130.00   0.50   17.87    --  107.75  77.00  30.00   52
 36  ω     83.00 114.00   0.50   17.87    --  107.75 -82.00 132.39   62
 37  ω     56.00 107.00   0.50   17.87    --  107.75-125.00  90.00  102
 38  ω     36.00  72.00   0.50   17.87    --  107.75 -77.00-120.00   72
 39  ω     56.00  91.00   0.50   17.87    --  107.75 -95.00  60.00   70
 40  ω     38.00  70.00   0.50   17.87    --  107.75 -61.00  30.00   64
 41  ω     43.00  70.00   0.50   17.87    --  107.75 -77.00-150.00   54
 42  ω     37.00  92.00   0.50   17.87    --  107.75 -77.00 150.00  110
 43  ω     38.00  89.00   0.50   17.87    --  107.75 -95.00 -90.00  102
 44  ω     55.00  81.00   0.50   17.87    --  107.75-125.00-150.00   52
 45  ω    124.00 178.00   0.50   17.87    --  107.75  45.00 -60.00  108
 46  ω    100.00 164.00   0.50   17.87    --  107.75  45.00  90.00  128
 47  ω     40.00  82.00   0.50   17.87    --  107.75 -87.00 -86.11   84
 48  ω     85.00 111.00   0.50   17.87    --  107.75 -87.00 -86.11   52
 49  ω     36.00  69.00   0.50   17.87    --  107.75 -61.00-180.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3958
_reflns_number_total             4433
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4433
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0655
_refine_ls_restrained_S_all      1.042
_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)+(0.0741P)²+2.2397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1740
_refine_ls_wR_factor_ref         0.1776
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1-C8A \\sim C1-C8B
 with sigma of 0.003
 C8A-C9A \\sim C8B-C9B
 with sigma of 0.003
 C8A-C13A \\sim C8B-C13B
 with sigma of 0.003
 C9A-C10A \\sim C9B-C10B
 with sigma of 0.003
 C10A-C11A \\sim C10B-C11B
 with sigma of 0.003
 C11A-C12A \\sim C11B-C12B
 with sigma of 0.003
 C12A-C13A \\sim C12B-C13B
 with sigma of 0.003
 C1-C19A \\sim C1-C19B
 with sigma of 0.003
 O4A-C19A \\sim O4B-C19B
 with sigma of 0.003
 O4A-C20A \\sim O4B-C20B
 with sigma of 0.003
 C20A-C21A \\sim C20B-C21B
 with sigma of 0.003
 C21A-N2A \\sim C21B-N2B
 with sigma of 0.003
 C19A-N2A \\sim N2B-C19B
 with sigma of 0.003
 C20A-C22A \\sim C20B-C22B
 with sigma of 0.003
 O5A-C23A \\sim O5B-C23B
 with sigma of 0.003
 C21A-C23A \\sim C21B-C23B
 with sigma of 0.003
 C23A-C24A \\sim C23B-C24B
 with sigma of 0.003
3. Uiso/Uaniso restraints and constraints
Uanis(C19A) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(C8A) = Uanis(C8B)
Uanis(C9A) = Uanis(C9B)
Uanis(C10A) = Uanis(C10B)
Uanis(C11A) = Uanis(C11B)
Uanis(C12A) = Uanis(C12B)
Uanis(C13A) = Uanis(C13B)
Uanis(C19A) = Uanis(C19B)
Uanis(N2A) = Uanis(O4B)
Uanis(O4A) = Uanis(N2B)
Uanis(C20A) = Uanis(C20B)
Uanis(C21A) = Uanis(C21B)
Uanis(C24A) = Uanis(C22B)
Uanis(C24B) = Uanis(C22A)
Uanis(C23A) = Uanis(C23B)
Uanis(O5A) = Uanis(O5B)
4. Others
 Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=
 Sof(H12B)=Sof(C13B)=Sof(H13B)=1-FVAR(1)
 Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=
 Sof(H12A)=Sof(C13A)=Sof(H13A)=FVAR(1)
 Sof(O4B)=Sof(O5B)=Sof(N2B)=Sof(C19B)=Sof(C20B)=Sof(C21B)=Sof(C22B)=Sof(H22D)=
 Sof(H22E)=Sof(H22F)=Sof(C23B)=Sof(C24B)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(2)
 Sof(O4A)=Sof(O5A)=Sof(N2A)=Sof(C19A)=Sof(C20A)=Sof(C21A)=Sof(C22A)=Sof(H22A)=
 Sof(H22B)=Sof(H22C)=Sof(C23A)=Sof(C24A)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9A(H9A), C9B(H9B), C10A(H10A),
 C10B(H10B), C11A(H11A), C11B(H11B), C12A(H12A), C12B(H12B), C13A(H13A),
 C13B(H13B)
5.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C22A(H22A,H22B,H22C), C22B(H22D,
 H22E,H22F), C24A(H24A,H24B,H24C), C24B(H24D,H24E,H24F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.45324(12) 0.59889(9) 0.65277(13) 0.0274(3) Uani 1 1 d . . . . .
O2 O 0.49920(16) 0.87768(11) 0.53792(17) 0.0426(4) Uani 1 1 d . . . . .
O3 O 0.64777(15) 0.74889(13) 0.76524(14) 0.0399(4) Uani 1 1 d . . . . .
O4A O 0.2712(2) 0.5124(2) 0.4737(3) 0.0252(6) Uani 0.5796(18) 1 d D . P A 1
O4B O 0.1611(4) 0.6055(3) 0.6052(3) 0.0254(7) Uani 0.4204(18) 1 d D . P A 2
O5A O -0.0638(2) 0.6135(2) 0.2939(2) 0.0350(6) Uani 0.5796(18) 1 d D . P A 1
O5B O -0.0340(3) 0.5757(3) 0.2661(4) 0.0350(6) Uani 0.4204(18) 1 d D . P A 2
N1 N 0.39927(16) 0.67944(11) 0.61240(15) 0.0261(4) Uani 1 1 d . . . . .
N2A N 0.1580(4) 0.5864(3) 0.5620(3) 0.0254(7) Uani 0.5796(18) 1 d D . P A 1
N2B N 0.2317(4) 0.5231(5) 0.4847(5) 0.0252(6) Uani 0.4204(18) 1 d D . P A 2
C1 C 0.36338(17) 0.54108(13) 0.67802(17) 0.0244(4) Uani 1 1 d D . . . .
C2 C 0.41379(18) 0.44725(13) 0.68209(16) 0.0257(4) Uani 1 1 d . . . . .
C3 C 0.52030(19) 0.42955(15) 0.65476(19) 0.0318(5) Uani 1 1 d . . . . .
H3 H 0.562661 0.475757 0.630104 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5645(2) 0.34373(17) 0.6637(2) 0.0393(6) Uani 1 1 d . . . . .
H4 H 0.637737 0.331826 0.646266 0.047 Uiso 1 1 calc R U . . .
C5 C 0.5026(3) 0.27601(16) 0.6978(2) 0.0428(6) Uani 1 1 d . . . . .
H5 H 0.533456 0.217764 0.704378 0.051 Uiso 1 1 calc R U . . .
C6 C 0.3951(3) 0.29337(15) 0.7225(2) 0.0384(6) Uani 1 1 d . . . . .
H6 H 0.351616 0.246599 0.744407 0.046 Uiso 1 1 calc R U . . .
C7 C 0.3510(2) 0.37837(15) 0.71534(18) 0.0315(5) Uani 1 1 d . . . . .
H7 H 0.277750 0.389846 0.733097 0.038 Uiso 1 1 calc R U . . .
C8A C 0.3549(7) 0.5637(11) 0.7980(5) 0.0230(14) Uani 0.630(15) 1 d D . P A 1
C8B C 0.3330(11) 0.569(2) 0.7878(10) 0.0230(14) Uani 0.370(15) 1 d D . P A 2
C9A C 0.4585(7) 0.5920(7) 0.8764(6) 0.0281(12) Uani 0.630(15) 1 d D . P A 1
H9A H 0.530104 0.599278 0.853920 0.034 Uiso 0.630(15) 1 calc R U P A 1
C9B C 0.4275(11) 0.5901(13) 0.8813(10) 0.0281(12) Uani 0.370(15) 1 d D . P A 2
H9B H 0.504203 0.596068 0.868892 0.034 Uiso 0.370(15) 1 calc R U P A 2
C10A C 0.4546(8) 0.6092(6) 0.9872(5) 0.0369(15) Uani 0.630(15) 1 d D . P A 1
H10A H 0.524703 0.627044 1.041692 0.044 Uiso 0.630(15) 1 calc R U P A 1
C10B C 0.4157(13) 0.6025(12) 0.9907(10) 0.0369(15) Uani 0.370(15) 1 d D . P A 2
H10B H 0.483125 0.616241 1.051009 0.044 Uiso 0.370(15) 1 calc R U P A 2
C11A C 0.3506(10) 0.6007(5) 1.0199(7) 0.0375(17) Uani 0.630(15) 1 d D . P A 1
H11A H 0.350325 0.611529 1.096904 0.045 Uiso 0.630(15) 1 calc R U P A 1
C11B C 0.3059(13) 0.5950(10) 1.0118(14) 0.0375(17) Uani 0.370(15) 1 d D . P A 2
H11B H 0.293860 0.608642 1.084424 0.045 Uiso 0.370(15) 1 calc R U P A 2
C12A C 0.2467(10) 0.5768(9) 0.9417(8) 0.043(2) Uani 0.630(15) 1 d D . P A 1
H12A H 0.174535 0.573105 0.963884 0.051 Uiso 0.630(15) 1 calc R U P A 1
C12B C 0.2138(16) 0.5668(16) 0.9227(15) 0.043(2) Uani 0.370(15) 1 d D . P A 2
H12B H 0.138623 0.556722 0.937056 0.051 Uiso 0.370(15) 1 calc R U P A 2
C13A C 0.2493(9) 0.5581(14) 0.8303(9) 0.0335(15) Uani 0.630(15) 1 d D . P A 1
H13A H 0.178494 0.541334 0.775931 0.040 Uiso 0.630(15) 1 calc R U P A 1
C13B C 0.2256(16) 0.552(3) 0.8131(18) 0.0335(15) Uani 0.370(15) 1 d D . P A 2
H13B H 0.160196 0.530864 0.755417 0.040 Uiso 0.370(15) 1 calc R U P A 2
C14 C 0.47573(18) 0.74008(14) 0.61438(17) 0.0255(4) Uani 1 1 d . . . . .
C15 C 0.4287(2) 0.82521(14) 0.55668(18) 0.0289(4) Uani 1 1 d . . . . .
C16 C 0.2974(2) 0.83851(16) 0.5211(2) 0.0352(5) Uani 1 1 d . . . . .
H16A H 0.279758 0.898020 0.490014 0.053 Uiso 1 1 calc R U . . .
H16B H 0.264818 0.831156 0.587292 0.053 Uiso 1 1 calc R U . . .
H16C H 0.261489 0.795069 0.462631 0.053 Uiso 1 1 calc R U . . .
C17 C 0.60854(19) 0.73125(14) 0.66509(18) 0.0275(4) Uani 1 1 d . . . . .
C18 C 0.6812(2) 0.70325(16) 0.5880(2) 0.0344(5) Uani 1 1 d . . . . .
H18A H 0.764938 0.702251 0.630118 0.052 Uiso 1 1 calc R U . . .
H18B H 0.669950 0.744757 0.524310 0.052 Uiso 1 1 calc R U . . .
H18C H 0.656728 0.644174 0.558615 0.052 Uiso 1 1 calc R U . . .
C19A C 0.2586(6) 0.5506(9) 0.5743(6) 0.0214(13) Uani 0.5796(18) 1 d D U P A 1
C19B C 0.2470(9) 0.5478(13) 0.5871(9) 0.0214(13) Uani 0.4204(18) 1 d D . P A 2
C20A C 0.1701(3) 0.5345(2) 0.3920(3) 0.0252(6) Uani 0.5796(18) 1 d D . P A 1
C20B C 0.0797(4) 0.6085(3) 0.5012(4) 0.0252(6) Uani 0.4204(18) 1 d D . P A 2
C21A C 0.0990(4) 0.5793(4) 0.4461(3) 0.0221(11) Uani 0.5796(18) 1 d D . P A 1
C21B C 0.1219(6) 0.5589(6) 0.4269(4) 0.0221(11) Uani 0.4204(18) 1 d D . P A 2
C22A C 0.1600(5) 0.5056(5) 0.2731(4) 0.0379(12) Uani 0.5796(18) 1 d D . P A 1
H22A H 0.181924 0.554448 0.229728 0.057 Uiso 0.5796(18) 1 calc R U P A 1
H22B H 0.078226 0.487695 0.237556 0.057 Uiso 0.5796(18) 1 calc R U P A 1
H22C H 0.213381 0.455727 0.273435 0.057 Uiso 0.5796(18) 1 calc R U P A 1
C22B C -0.0286(6) 0.6616(7) 0.4952(9) 0.0377(11) Uani 0.4204(18) 1 d D . P A 2
H22D H -0.097293 0.622355 0.484160 0.057 Uiso 0.4204(18) 1 calc R U P A 2
H22E H -0.040835 0.702868 0.431141 0.057 Uiso 0.4204(18) 1 calc R U P A 2
H22F H -0.019186 0.694605 0.566393 0.057 Uiso 0.4204(18) 1 calc R U P A 2
C23A C -0.0164(3) 0.6196(2) 0.3956(3) 0.0277(6) Uani 0.5796(18) 1 d D . P A 1
C23B C 0.0650(4) 0.5457(3) 0.3059(4) 0.0277(6) Uani 0.4204(18) 1 d D . P A 2
C24A C -0.0717(4) 0.6671(5) 0.4757(6) 0.0377(11) Uani 0.5796(18) 1 d D . P A 1
H24A H -0.101558 0.624334 0.522032 0.057 Uiso 0.5796(18) 1 calc R U P A 1
H24B H -0.137527 0.703247 0.432314 0.057 Uiso 0.5796(18) 1 calc R U P A 1
H24C H -0.012514 0.705064 0.525603 0.057 Uiso 0.5796(18) 1 calc R U P A 1
C24B C 0.1318(8) 0.4979(8) 0.2359(6) 0.0379(12) Uani 0.4204(18) 1 d D . P A 2
H24D H 0.206373 0.528763 0.239418 0.057 Uiso 0.4204(18) 1 calc R U P A 2
H24E H 0.084284 0.495361 0.156565 0.057 Uiso 0.4204(18) 1 calc R U P A 2
H24F H 0.148958 0.437857 0.265340 0.057 Uiso 0.4204(18) 1 calc R U P A 2


_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 N1 1.405(2) . ?
O1 C1 1.460(2) . ?
O2 C15 1.209(3) . ?
O3 C17 1.213(3) . ?
O4A C19A 1.393(11) . ?
O4A C20A 1.373(4) . ?
O4B C19B 1.390(12) . ?
O4B C20B 1.371(4) . ?
O5A C23A 1.219(4) . ?
O5B C23B 1.220(4) . ?
N1 C14 1.278(3) . ?
N2A C19A 1.268(9) . ?
N2A C21A 1.403(4) . ?
N2B C19B 1.266(10) . ?
N2B C21B 1.403(4) . ?
C1 C2 1.537(3) . ?
C1 C8A 1.525(3) . ?
C1 C8B 1.525(4) . ?
C1 C19A 1.519(3) . ?
C1 C19B 1.517(3) . ?
C2 C3 1.394(3) . ?
C2 C7 1.395(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(3) . ?
C7 H7 0.9500 . ?
C8A C9A 1.400(4) . ?
C8A C13A 1.389(4) . ?
C8B C9B 1.401(5) . ?
C8B C13B 1.389(5) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.382(4) . ?
C9B H9B 0.9500 . ?
C9B C10B 1.383(5) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.376(6) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.376(6) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.382(6) . ?
C11B H11B 0.9500 . ?
C11B C12B 1.382(6) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.390(4) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.390(4) . ?
C13A H13A 0.9500 . ?
C13B H13B 0.9500 . ?
C14 C15 1.505(3) . ?
C14 C17 1.520(3) . ?
C15 C16 1.495(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.478(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20A C21A 1.365(5) . ?
C20A C22A 1.484(5) . ?
C20B C21B 1.361(5) . ?
C20B C22B 1.485(6) . ?
C21A C23A 1.462(4) . ?
C21B C23B 1.462(4) . ?
C22A H22A 0.9800 . ?
C22A H22B 0.9800 . ?
C22A H22C 0.9800 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?
C23A C24A 1.485(7) . ?
C23B C24B 1.483(7) . ?
C24A H24A 0.9800 . ?
C24A H24B 0.9800 . ?
C24A H24C 0.9800 . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 C1 108.32(14) . . ?
C20A O4A C19A 105.4(3) . . ?
C20B O4B C19B 103.5(4) . . ?
C14 N1 O1 111.83(16) . . ?
C19A N2A C21A 106.6(5) . . ?
C19B N2B C21B 104.8(5) . . ?
O1 C1 C2 105.88(16) . . ?
O1 C1 C8A 107.0(5) . . ?
O1 C1 C8B 111.0(9) . . ?
O1 C1 C19A 103.8(5) . . ?
O1 C1 C19B 111.4(8) . . ?
C8A C1 C2 107.3(7) . . ?
C8B C1 C2 113.8(12) . . ?
C19A C1 C2 109.5(5) . . ?
C19A C1 C8A 122.2(6) . . ?
C19B C1 C2 110.5(7) . . ?
C19B C1 C8B 104.5(8) . . ?
C3 C2 C1 121.94(19) . . ?
C3 C2 C7 119.5(2) . . ?
C7 C2 C1 118.55(19) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.1(2) . . ?
C6 C7 H7 120.0 . . ?
C9A C8A C1 117.4(5) . . ?
C13A C8A C1 122.5(6) . . ?
C13A C8A C9A 120.1(4) . . ?
C9B C8B C1 117.3(9) . . ?
C13B C8B C1 124.6(13) . . ?
C13B C8B C9B 115.5(11) . . ?
C8A C9A H9A 120.7 . . ?
C10A C9A C8A 118.6(4) . . ?
C10A C9A H9A 120.7 . . ?
C8B C9B H9B 118.1 . . ?
C10B C9B C8B 123.8(9) . . ?
C10B C9B H9B 118.1 . . ?
C9A C10A H10A 119.5 . . ?
C11A C10A C9A 121.1(5) . . ?
C11A C10A H10A 119.5 . . ?
C9B C10B H10B 120.1 . . ?
C11B C10B C9B 119.8(12) . . ?
C11B C10B H10B 120.1 . . ?
C10A C11A H11A 119.7 . . ?
C10A C11A C12A 120.6(7) . . ?
C12A C11A H11A 119.7 . . ?
C10B C11B H11B 121.5 . . ?
C10B C11B C12B 117.0(15) . . ?
C12B C11B H11B 121.5 . . ?
C11A C12A H12A 120.5 . . ?
C11A C12A C13A 119.1(8) . . ?
C13A C12A H12A 120.5 . . ?
C11B C12B H12B 118.3 . . ?
C11B C12B C13B 123.3(18) . . ?
C13B C12B H12B 118.3 . . ?
C8A C13A C12A 120.4(7) . . ?
C8A C13A H13A 119.8 . . ?
C12A C13A H13A 119.8 . . ?
C8B C13B C12B 120.0(15) . . ?
C8B C13B H13B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
N1 C14 C15 116.11(18) . . ?
N1 C14 C17 125.38(19) . . ?
C15 C14 C17 118.45(18) . . ?
O2 C15 C14 117.9(2) . . ?
O2 C15 C16 123.7(2) . . ?
C16 C15 C14 118.33(19) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 C14 117.9(2) . . ?
O3 C17 C18 124.6(2) . . ?
C18 C17 C14 117.47(18) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4A C19A C1 116.2(6) . . ?
N2A C19A O4A 112.3(3) . . ?
N2A C19A C1 131.4(8) . . ?
O4B C19B C1 118.4(8) . . ?
N2B C19B O4B 114.6(5) . . ?
N2B C19B C1 124.5(9) . . ?
O4A C20A C22A 117.9(4) . . ?
C21A C20A O4A 106.9(3) . . ?
C21A C20A C22A 135.2(3) . . ?
O4B C20B C22B 116.3(5) . . ?
C21B C20B O4B 107.9(4) . . ?
C21B C20B C22B 135.8(6) . . ?
N2A C21A C23A 123.3(3) . . ?
C20A C21A N2A 108.5(3) . . ?
C20A C21A C23A 128.0(3) . . ?
N2B C21B C23B 124.7(4) . . ?
C20B C21B N2B 108.8(4) . . ?
C20B C21B C23B 126.4(4) . . ?
C20A C22A H22A 109.5 . . ?
C20A C22A H22B 109.5 . . ?
C20A C22A H22C 109.5 . . ?
H22A C22A H22B 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C20B C22B H22D 109.5 . . ?
C20B C22B H22E 109.5 . . ?
C20B C22B H22F 109.5 . . ?
H22D C22B H22E 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
O5A C23A C21A 121.4(3) . . ?
O5A C23A C24A 122.6(4) . . ?
C21A C23A C24A 116.0(3) . . ?
O5B C23B C21B 119.0(4) . . ?
O5B C23B C24B 122.7(5) . . ?
C21B C23B C24B 118.2(4) . . ?
C23A C24A H24A 109.5 . . ?
C23A C24A H24B 109.5 . . ?
C23A C24A H24C 109.5 . . ?
H24A C24A H24B 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
C23B C24B H24D 109.5 . . ?
C23B C24B H24E 109.5 . . ?
C23B C24B H24F 109.5 . . ?
H24D C24B H24E 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 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
O1 N1 C14 C15 171.08(16) . . . . ?
O1 N1 C14 C17 -6.1(3) . . . . ?
O1 C1 C2 C3 -5.2(2) . . . . ?
O1 C1 C2 C7 174.12(17) . . . . ?
O1 C1 C8A C9A -32.2(14) . . . . ?
O1 C1 C8A C13A 147.1(16) . . . . ?
O1 C1 C8B C9B -45(3) . . . . ?
O1 C1 C8B C13B 154(3) . . . . ?
O1 C1 C19A O4A 71.0(10) . . . . ?
O1 C1 C19A N2A -110.4(13) . . . . ?
O1 C1 C19B O4B -94.8(14) . . . . ?
O1 C1 C19B N2B 66.3(19) . . . . ?
O4A C20A C21A N2A 1.2(6) . . . . ?
O4A C20A C21A C23A 177.4(5) . . . . ?
O4B C20B C21B N2B 0.4(10) . . . . ?
O4B C20B C21B C23B -178.4(8) . . . . ?
N1 O1 C1 C2 161.41(15) . . . . ?
N1 O1 C1 C8A -84.4(6) . . . . ?
N1 O1 C1 C8B -74.6(11) . . . . ?
N1 O1 C1 C19A 46.1(5) . . . . ?
N1 O1 C1 C19B 41.3(6) . . . . ?
N1 C14 C15 O2 -166.5(2) . . . . ?
N1 C14 C15 C16 10.8(3) . . . . ?
N1 C14 C17 O3 -89.0(3) . . . . ?
N1 C14 C17 C18 92.1(3) . . . . ?
N2A C21A C23A O5A 178.4(5) . . . . ?
N2A C21A C23A C24A -2.2(8) . . . . ?
N2B C21B C23B O5B 175.7(8) . . . . ?
N2B C21B C23B C24B -5.8(13) . . . . ?
C1 O1 N1 C14 164.32(17) . . . . ?
C1 C2 C3 C4 177.68(19) . . . . ?
C1 C2 C7 C6 -178.51(19) . . . . ?
C1 C8A C9A C10A -177.1(10) . . . . ?
C1 C8A C13A C12A 178.0(15) . . . . ?
C1 C8B C9B C10B -169.1(19) . . . . ?
C1 C8B C13B C12B 169(3) . . . . ?
C2 C1 C8A C9A 81.1(13) . . . . ?
C2 C1 C8A C13A -99.6(16) . . . . ?
C2 C1 C8B C9B 75(3) . . . . ?
C2 C1 C8B C13B -86(3) . . . . ?
C2 C1 C19A O4A -41.7(11) . . . . ?
C2 C1 C19A N2A 136.9(13) . . . . ?
C2 C1 C19B O4B 147.8(12) . . . . ?
C2 C1 C19B N2B -51(2) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C2 C7 C6 0.9(3) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C7 -1.3(4) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
C7 C2 C3 C4 -1.7(3) . . . . ?
C8A C1 C2 C3 -119.2(4) . . . . ?
C8A C1 C2 C7 60.1(4) . . . . ?
C8A C1 C19A O4A -168.3(10) . . . . ?
C8A C1 C19A N2A 10.3(19) . . . . ?
C8A C9A C10A C11A -1.5(16) . . . . ?
C8B C1 C2 C3 -127.4(6) . . . . ?
C8B C1 C2 C7 52.0(6) . . . . ?
C8B C1 C19B O4B 25(2) . . . . ?
C8B C1 C19B N2B -174(2) . . . . ?
C8B C9B C10B C11B 0(3) . . . . ?
C9A C8A C13A C12A -3(3) . . . . ?
C9A C10A C11A C12A -1.5(15) . . . . ?
C9B C8B C13B C12B 7(5) . . . . ?
C9B C10B C11B C12B 6(3) . . . . ?
C10A C11A C12A C13A 2(2) . . . . ?
C10B C11B C12B C13B -5(4) . . . . ?
C11A C12A C13A C8A 0(3) . . . . ?
C11B C12B C13B C8B -2(5) . . . . ?
C13A C8A C9A C10A 4(2) . . . . ?
C13B C8B C9B C10B -6(4) . . . . ?
C15 C14 C17 O3 93.8(2) . . . . ?
C15 C14 C17 C18 -85.1(2) . . . . ?
C17 C14 C15 O2 10.9(3) . . . . ?
C17 C14 C15 C16 -171.76(19) . . . . ?
C19A O4A C20A C21A -3.5(8) . . . . ?
C19A O4A C20A C22A 177.6(7) . . . . ?
C19A N2A C21A C20A 1.9(9) . . . . ?
C19A N2A C21A C23A -174.6(8) . . . . ?
C19A C1 C2 C3 106.1(5) . . . . ?
C19A C1 C2 C7 -74.6(5) . . . . ?
C19A C1 C8A C9A -151.3(11) . . . . ?
C19A C1 C8A C13A 28(2) . . . . ?
C19B O4B C20B C21B -3.4(11) . . . . ?
C19B O4B C20B C22B 176.3(11) . . . . ?
C19B N2B C21B C20B 3.1(14) . . . . ?
C19B N2B C21B C23B -178.1(12) . . . . ?
C19B C1 C2 C3 115.5(7) . . . . ?
C19B C1 C2 C7 -65.2(7) . . . . ?
C19B C1 C8B C9B -165(2) . . . . ?
C19B C1 C8B C13B 34(4) . . . . ?
C20A O4A C19A N2A 5.0(12) . . . . ?
C20A O4A C19A C1 -176.1(8) . . . . ?
C20A C21A C23A O5A 2.7(9) . . . . ?
C20A C21A C23A C24A -177.9(6) . . . . ?
C20B O4B C19B N2B 5.9(17) . . . . ?
C20B O4B C19B C1 168.8(12) . . . . ?
C20B C21B C23B O5B -5.8(13) . . . . ?
C20B C21B C23B C24B 172.8(10) . . . . ?
C21A N2A C19A O4A -4.3(12) . . . . ?
C21A N2A C19A C1 177.1(11) . . . . ?
C21B N2B C19B O4B -5.6(18) . . . . ?
C21B N2B C19B C1 -167.3(14) . . . . ?
C22A C20A C21A N2A 179.8(6) . . . . ?
C22A C20A C21A C23A -3.9(11) . . . . ?
C22B C20B C21B N2B -179.2(9) . . . . ?
C22B C20B C21B C23B 2.0(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
