# Electronic Supplementary Material (ESI) for Green 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_Ga393
_database_code_depnum_ccdc_archive 'CCDC 2207558'
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             
;
2022-09-15 deposited with the CCDC.	2023-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'Dimethyl 1-hydroxy-1,3,3a,3a1,5a,5a1,6,8,8a,10a-decahydro-3a,5a:8a,10adiepoxyisochromeno[ 6,5,4-def]isochromene-4,5-dicarboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 O9'
_chemical_formula_sum            'C18 H18 O9'

_chemical_formula_weight         378.32

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   18.6508(3)
_cell_length_b                   5.87960(10)
_cell_length_c                   14.7464(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.7151(7)
_cell_angle_gamma                90
_cell_volume                     1611.61(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9847
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      31.47

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8256
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 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            51521
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.772
_diffrn_reflns_theta_max         31.523
_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             5388
_reflns_number_gt                4465
_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, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    
'SHELXT, 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 (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_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)+(0.0300P)²+0.3913P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5388
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0707
_refine_ls_wR_factor_gt          0.0647
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_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 0.69727(3) 0.81935(9) 0.29507(4) 0.01230(12) Uani 1 1 d . . . . .
O2 O 0.64602(3) 0.45665(10) 0.59978(4) 0.01288(12) Uani 1 1 d . . . . .
O3 O 0.60480(3) 0.56604(9) 0.41060(4) 0.01023(11) Uani 1 1 d . . . . .
O4 O 0.74344(3) 0.56910(9) 0.46036(4) 0.01010(11) Uani 1 1 d . . . . .
O5 O 0.63916(3) 0.61823(10) 0.17319(4) 0.01427(12) Uani 1 1 d . . . . .
H5 H 0.6411(8) 0.750(3) 0.1363(10) 0.048(4) Uiso 1 1 d . . . . .
O6 O 0.83421(4) -0.02276(12) 0.59414(4) 0.01953(14) Uani 1 1 d . . . . .
O7 O 0.89528(3) -0.03906(11) 0.46834(4) 0.01553(13) Uani 1 1 d . . . . .
O8 O 0.93413(3) 0.38711(12) 0.33979(4) 0.02027(14) Uani 1 1 d . . . . .
O9 O 0.85912(3) 0.13089(11) 0.26950(4) 0.01702(13) Uani 1 1 d . . . . .
C1 C 0.63454(4) 0.69873(13) 0.26185(5) 0.01084(14) Uani 1 1 d . . . . .
H1 H 0.5948(6) 0.8187(19) 0.2653(7) 0.015(3) Uiso 1 1 d . . . . .
C2 C 0.62129(4) 0.49488(13) 0.32130(5) 0.00892(14) Uani 1 1 d . . . . .
C3 C 0.56070(4) 0.32546(14) 0.29772(5) 0.01159(14) Uani 1 1 d . . . . .
H3 H 0.5412(6) 0.279(2) 0.2335(8) 0.028(3) Uiso 1 1 d . . . . .
C4 C 0.54749(4) 0.22914(14) 0.37714(5) 0.01188(15) Uani 1 1 d . . . . .
H4 H 0.5151(7) 0.093(2) 0.3885(8) 0.029(3) Uiso 1 1 d . . . . .
C5 C 0.60023(4) 0.34053(13) 0.44841(5) 0.00926(14) Uani 1 1 d . . . . .
C6 C 0.58793(4) 0.34460(14) 0.54802(5) 0.01206(14) Uani 1 1 d . . . . .
H6A H 0.5435(6) 0.434(2) 0.5601(8) 0.018(3) Uiso 1 1 d . . . . .
H6B H 0.5816(6) 0.179(2) 0.5706(8) 0.019(3) Uiso 1 1 d . . . . .
C7 C 0.71536(4) 0.35306(14) 0.59507(5) 0.01206(15) Uani 1 1 d . . . . .
H7A H 0.7142(6) 0.194(2) 0.6194(8) 0.021(3) Uiso 1 1 d . . . . .
H7B H 0.7496(6) 0.452(2) 0.6355(7) 0.017(3) Uiso 1 1 d . . . . .
C8 C 0.73536(4) 0.34511(13) 0.49805(5) 0.00902(14) Uani 1 1 d . . . . .
C9 C 0.80535(4) 0.23428(13) 0.47160(5) 0.01026(14) Uani 1 1 d . . . . .
C10 C 0.81814(4) 0.33070(13) 0.39173(5) 0.00959(14) Uani 1 1 d . . . . .
C11 C 0.75602(4) 0.49747(12) 0.36997(5) 0.00863(13) Uani 1 1 d . . . . .
C12 C 0.76291(4) 0.69198(13) 0.30529(5) 0.01172(14) Uani 1 1 d . . . . .
H12A H 0.8020(6) 0.803(2) 0.3307(8) 0.021(3) Uiso 1 1 d . . . . .
H12B H 0.7772(6) 0.630(2) 0.2438(8) 0.021(3) Uiso 1 1 d . . . . .
C13 C 0.68985(4) 0.34700(12) 0.34180(5) 0.00801(13) Uani 1 1 d . . . . .
H13 H 0.6986(5) 0.2369(19) 0.2916(7) 0.012(2) Uiso 1 1 d . . . . .
C14 C 0.67493(4) 0.23834(13) 0.43279(5) 0.00848(13) Uani 1 1 d . . . . .
H14 H 0.6746(6) 0.0629(19) 0.4356(7) 0.014(3) Uiso 1 1 d . . . . .
C15 C 0.84474(4) 0.04565(14) 0.51894(5) 0.01116(14) Uani 1 1 d . . . . .
C16 C 0.93755(5) -0.22322(16) 0.50888(7) 0.01919(17) Uani 1 1 d . . . . .
H16A H 0.9734(7) -0.260(2) 0.4632(9) 0.037(4) Uiso 1 1 d . . . . .
H16B H 0.9050(7) -0.362(2) 0.5190(9) 0.038(4) Uiso 1 1 d . . . . .
H16C H 0.9627(7) -0.173(2) 0.5694(9) 0.032(3) Uiso 1 1 d . . . . .
C17 C 0.87742(4) 0.28741(13) 0.33235(5) 0.01077(14) Uani 1 1 d . . . . .
C18 C 0.91516(6) 0.0642(2) 0.21290(8) 0.0284(2) Uani 1 1 d . . . . .
H18A H 0.8940(9) -0.062(3) 0.1735(11) 0.061(5) Uiso 1 1 d . . . . .
H18B H 0.9597(8) 0.016(3) 0.2528(10) 0.042(4) Uiso 1 1 d . . . . .
H18C H 0.9281(8) 0.197(3) 0.1730(9) 0.041(4) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4205(9) . ?
O1 C12 1.4324(10) . ?
O2 C6 1.4333(10) . ?
O2 C7 1.4363(10) . ?
O3 C2 1.4389(9) . ?
O3 C5 1.4436(9) . ?
O4 C11 1.4355(9) . ?
O4 C8 1.4421(9) . ?
O5 C1 1.3997(9) . ?
O5 H5 0.947(16) . ?
O6 C15 1.2107(10) . ?
O7 C15 1.3450(10) . ?
O7 C16 1.4402(10) . ?
O8 C17 1.2064(10) . ?
O9 C17 1.3306(10) . ?
O9 C18 1.4443(11) . ?
C1 C2 1.5172(11) . ?
C1 H1 1.027(11) . ?
C2 C3 1.5250(11) . ?
C2 C13 1.5552(10) . ?
C3 C4 1.3418(11) . ?
C3 H3 1.023(12) . ?
C4 C5 1.5268(11) . ?
C4 H4 1.023(13) . ?
C5 C6 1.5053(11) . ?
C5 C14 1.5517(10) . ?
C6 H6A 1.008(12) . ?
C6 H6B 1.037(12) . ?
C7 C8 1.5087(10) . ?
C7 H7A 1.004(12) . ?
C7 H7B 1.019(11) . ?
C8 C9 1.5375(10) . ?
C8 C14 1.5531(10) . ?
C9 C10 1.3460(10) . ?
C9 C15 1.4741(11) . ?
C10 C17 1.4876(10) . ?
C10 C11 1.5315(10) . ?
C11 C12 1.5014(11) . ?
C11 C13 1.5474(10) . ?
C12 H12A 1.028(12) . ?
C12 H12B 1.033(12) . ?
C13 C14 1.5321(10) . ?
C13 H13 1.006(11) . ?
C14 H14 1.032(11) . ?
C16 H16A 1.011(14) . ?
C16 H16B 1.033(14) . ?
C16 H16C 1.017(13) . ?
C18 H18A 1.004(18) . ?
C18 H18B 1.018(15) . ?
C18 H18C 1.020(15) . ?

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 O1 C12 116.61(6) . . ?
C6 O2 C7 115.06(6) . . ?
C2 O3 C5 96.33(5) . . ?
C11 O4 C8 96.90(5) . . ?
C1 O5 H5 105.6(9) . . ?
C15 O7 C16 115.65(7) . . ?
C17 O9 C18 115.72(7) . . ?
O5 C1 O1 112.25(6) . . ?
O5 C1 C2 107.34(6) . . ?
O1 C1 C2 111.33(6) . . ?
O5 C1 H1 112.2(6) . . ?
O1 C1 H1 102.6(6) . . ?
C2 C1 H1 111.2(6) . . ?
O3 C2 C1 110.88(6) . . ?
O3 C2 C3 100.86(6) . . ?
C1 C2 C3 122.49(6) . . ?
O3 C2 C13 102.64(6) . . ?
C1 C2 C13 112.56(6) . . ?
C3 C2 C13 105.14(6) . . ?
C4 C3 C2 105.22(7) . . ?
C4 C3 H3 128.2(7) . . ?
C2 C3 H3 125.8(7) . . ?
C3 C4 C5 105.40(7) . . ?
C3 C4 H4 128.8(7) . . ?
C5 C4 H4 125.3(7) . . ?
O3 C5 C6 112.38(6) . . ?
O3 C5 C4 100.56(6) . . ?
C6 C5 C4 122.50(6) . . ?
O3 C5 C14 102.48(6) . . ?
C6 C5 C14 111.21(6) . . ?
C4 C5 C14 105.50(6) . . ?
O2 C6 C5 110.96(6) . . ?
O2 C6 H6A 105.3(7) . . ?
C5 C6 H6A 112.0(6) . . ?
O2 C6 H6B 111.2(6) . . ?
C5 C6 H6B 109.2(6) . . ?
H6A C6 H6B 108.2(9) . . ?
O2 C7 C8 110.66(6) . . ?
O2 C7 H7A 109.4(7) . . ?
C8 C7 H7A 108.9(7) . . ?
O2 C7 H7B 104.6(6) . . ?
C8 C7 H7B 112.4(6) . . ?
H7A C7 H7B 110.8(9) . . ?
O4 C8 C7 112.27(6) . . ?
O4 C8 C9 99.88(6) . . ?
C7 C8 C9 122.35(6) . . ?
O4 C8 C14 102.93(6) . . ?
C7 C8 C14 112.13(6) . . ?
C9 C8 C14 105.04(6) . . ?
C10 C9 C15 127.88(7) . . ?
C10 C9 C8 105.00(6) . . ?
C15 C9 C8 126.81(6) . . ?
C9 C10 C17 129.55(7) . . ?
C9 C10 C11 105.52(6) . . ?
C17 C10 C11 124.90(6) . . ?
O4 C11 C12 113.30(6) . . ?
O4 C11 C10 99.90(6) . . ?
C12 C11 C10 121.20(6) . . ?
O4 C11 C13 103.25(6) . . ?
C12 C11 C13 111.90(6) . . ?
C10 C11 C13 105.26(6) . . ?
O1 C12 C11 110.37(6) . . ?
O1 C12 H12A 106.2(7) . . ?
C11 C12 H12A 110.4(7) . . ?
O1 C12 H12B 111.8(6) . . ?
C11 C12 H12B 109.3(7) . . ?
H12A C12 H12B 108.7(9) . . ?
C14 C13 C11 101.63(6) . . ?
C14 C13 C2 101.41(6) . . ?
C11 C13 C2 110.94(6) . . ?
C14 C13 H13 115.3(6) . . ?
C11 C13 H13 113.1(6) . . ?
C2 C13 H13 113.4(6) . . ?
C13 C14 C5 101.44(6) . . ?
C13 C14 C8 101.50(6) . . ?
C5 C14 C8 111.48(6) . . ?
C13 C14 H14 117.0(6) . . ?
C5 C14 H14 111.9(6) . . ?
C8 C14 H14 112.6(6) . . ?
O6 C15 O7 123.98(7) . . ?
O6 C15 C9 124.87(7) . . ?
O7 C15 C9 111.13(6) . . ?
O7 C16 H16A 104.6(8) . . ?
O7 C16 H16B 110.1(8) . . ?
H16A C16 H16B 111.0(11) . . ?
O7 C16 H16C 110.0(8) . . ?
H16A C16 H16C 111.4(10) . . ?
H16B C16 H16C 109.7(10) . . ?
O8 C17 O9 124.90(7) . . ?
O8 C17 C10 123.49(7) . . ?
O9 C17 C10 111.58(6) . . ?
O9 C18 H18A 105.5(9) . . ?
O9 C18 H18B 109.7(8) . . ?
H18A C18 H18B 112.9(13) . . ?
O9 C18 H18C 110.0(8) . . ?
H18A C18 H18C 109.6(12) . . ?
H18B C18 H18C 109.1(11) . . ?

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
C12 O1 C1 O5 -63.76(8) . . . . ?
C12 O1 C1 C2 56.61(8) . . . . ?
C5 O3 C2 C1 -176.65(6) . . . . ?
C5 O3 C2 C3 52.16(6) . . . . ?
C5 O3 C2 C13 -56.23(6) . . . . ?
O5 C1 C2 O3 -171.10(6) . . . . ?
O1 C1 C2 O3 65.68(8) . . . . ?
O5 C1 C2 C3 -52.29(9) . . . . ?
O1 C1 C2 C3 -175.51(6) . . . . ?
O5 C1 C2 C13 74.56(8) . . . . ?
O1 C1 C2 C13 -48.66(8) . . . . ?
O3 C2 C3 C4 -33.09(8) . . . . ?
C1 C2 C3 C4 -156.62(7) . . . . ?
C13 C2 C3 C4 73.33(7) . . . . ?
C2 C3 C4 C5 -0.07(8) . . . . ?
C2 O3 C5 C6 176.05(6) . . . . ?
C2 O3 C5 C4 -52.06(6) . . . . ?
C2 O3 C5 C14 56.59(6) . . . . ?
C3 C4 C5 O3 33.06(8) . . . . ?
C3 C4 C5 C6 158.37(7) . . . . ?
C3 C4 C5 C14 -73.19(8) . . . . ?
C7 O2 C6 C5 -60.59(8) . . . . ?
O3 C5 C6 O2 -60.99(8) . . . . ?
C4 C5 C6 O2 179.19(7) . . . . ?
C14 C5 C6 O2 53.24(8) . . . . ?
C6 O2 C7 C8 59.23(9) . . . . ?
C11 O4 C8 C7 -175.76(6) . . . . ?
C11 O4 C8 C9 53.08(6) . . . . ?
C11 O4 C8 C14 -54.99(6) . . . . ?
O2 C7 C8 O4 64.02(8) . . . . ?
O2 C7 C8 C9 -177.38(6) . . . . ?
O2 C7 C8 C14 -51.30(8) . . . . ?
O4 C8 C9 C10 -33.03(7) . . . . ?
C7 C8 C9 C10 -157.47(7) . . . . ?
C14 C8 C9 C10 73.35(7) . . . . ?
O4 C8 C9 C15 153.04(7) . . . . ?
C7 C8 C9 C15 28.60(12) . . . . ?
C14 C8 C9 C15 -100.58(8) . . . . ?
C15 C9 C10 C17 -4.70(14) . . . . ?
C8 C9 C10 C17 -178.54(7) . . . . ?
C15 C9 C10 C11 173.52(7) . . . . ?
C8 C9 C10 C11 -0.32(8) . . . . ?
C8 O4 C11 C12 176.37(6) . . . . ?
C8 O4 C11 C10 -53.27(6) . . . . ?
C8 O4 C11 C13 55.13(6) . . . . ?
C9 C10 C11 O4 33.75(7) . . . . ?
C17 C10 C11 O4 -147.92(7) . . . . ?
C9 C10 C11 C12 158.85(7) . . . . ?
C17 C10 C11 C12 -22.82(11) . . . . ?
C9 C10 C11 C13 -73.04(7) . . . . ?
C17 C10 C11 C13 105.29(8) . . . . ?
C1 O1 C12 C11 -59.28(8) . . . . ?
O4 C11 C12 O1 -62.55(8) . . . . ?
C10 C11 C12 O1 178.79(6) . . . . ?
C13 C11 C12 O1 53.69(8) . . . . ?
O4 C11 C13 C14 -33.78(7) . . . . ?
C12 C11 C13 C14 -155.96(6) . . . . ?
C10 C11 C13 C14 70.53(7) . . . . ?
O4 C11 C13 C2 73.38(7) . . . . ?
C12 C11 C13 C2 -48.80(8) . . . . ?
C10 C11 C13 C2 177.69(6) . . . . ?
O3 C2 C13 C14 34.17(7) . . . . ?
C1 C2 C13 C14 153.42(6) . . . . ?
C3 C2 C13 C14 -70.95(7) . . . . ?
O3 C2 C13 C11 -73.14(7) . . . . ?
C1 C2 C13 C11 46.11(8) . . . . ?
C3 C2 C13 C11 -178.25(6) . . . . ?
C11 C13 C14 C5 114.95(6) . . . . ?
C2 C13 C14 C5 0.50(7) . . . . ?
C11 C13 C14 C8 -0.04(7) . . . . ?
C2 C13 C14 C8 -114.49(6) . . . . ?
O3 C5 C14 C13 -34.90(7) . . . . ?
C6 C5 C14 C13 -155.18(6) . . . . ?
C4 C5 C14 C13 69.94(7) . . . . ?
O3 C5 C14 C8 72.46(7) . . . . ?
C6 C5 C14 C8 -47.83(8) . . . . ?
C4 C5 C14 C8 177.29(6) . . . . ?
O4 C8 C14 C13 33.64(7) . . . . ?
C7 C8 C14 C13 154.51(6) . . . . ?
C9 C8 C14 C13 -70.48(7) . . . . ?
O4 C8 C14 C5 -73.68(7) . . . . ?
C7 C8 C14 C5 47.19(8) . . . . ?
C9 C8 C14 C5 -177.80(6) . . . . ?
C16 O7 C15 O6 0.52(12) . . . . ?
C16 O7 C15 C9 179.36(7) . . . . ?
C10 C9 C15 O6 174.06(8) . . . . ?
C8 C9 C15 O6 -13.38(13) . . . . ?
C10 C9 C15 O7 -4.77(12) . . . . ?
C8 C9 C15 O7 167.79(7) . . . . ?
C18 O9 C17 O8 6.23(12) . . . . ?
C18 O9 C17 C10 -175.40(8) . . . . ?
C9 C10 C17 O8 -89.19(11) . . . . ?
C11 C10 C17 O8 92.91(10) . . . . ?
C9 C10 C17 O9 92.41(10) . . . . ?
C11 C10 C17 O9 -85.49(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5 O2 0.947(16) 1.814(17) 2.7311(8) 162.3(13) 4_575 yes

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_gf632
_database_code_depnum_ccdc_archive 'CCDC 2207565'
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             
;
2022-09-15 deposited with the CCDC.	2023-01-02 downloaded from the CCDC.
;
_audit_creation_date             2022-04-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'(5-Benzoyl-4-(methoxycarbonyl)-3a1,6a-dihydro-1H,3H,6H,7H-3a,6:7,9adiepoxybenzo[ de]isochromene-6,7-diyl)bis(methylene) dibenzoate'
_chemical_formula_moiety         'C37 H30 O10'
_chemical_formula_sum            'C37 H30 O10'
_chemical_formula_weight         634.61
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     GF632
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.3610(2)
_cell_length_b                   13.3550(3)
_cell_length_c                   13.4649(3)
_cell_angle_alpha                62.271(2)
_cell_angle_beta                 70.487(2)
_cell_angle_gamma                70.729(2)
_cell_volume                     1520.04(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14975
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.8870
_cell_measurement_theta_min      3.7970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.840
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21798
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.670
_diffrn_reflns_theta_min         3.798
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -47.00   0.50    0.50    --  -48.76-165.00  11.00  146
  2  ω    -97.00 -72.00   0.50    0.50    --  -48.76 165.00  34.00   50
  3  ω    -61.00 -35.00   0.50    0.50    --  -48.76 116.00-113.00   52
  4  ω     71.00  96.00   0.50    0.50    --   48.76 165.00  34.00   50
  5  ω     59.00  88.00   0.50    0.50    --   48.76-116.00 158.00   58
  6  ω     64.00  89.00   0.50    0.50    --   48.76-165.00  11.00   50
  7  ω   -144.00-119.00   0.50    1.50    --  -90.00-116.00 158.00   50
  8  ω   -117.00 -92.00   0.50    1.50    --  -90.00-165.00  11.00   50
  9  ω    114.00 139.00   0.50    1.50    --  111.50-165.00  11.00   50
 10  ω    115.00 140.00   0.50    1.50    --  111.50 116.00-113.00   50
 11  ω     72.00 109.00   0.50    1.50    --  111.50-116.00 158.00   74
 12  ω     44.00  69.00   0.50    1.50    --  111.50-116.00 158.00   50
 13  ω    -18.00  24.00   0.50    0.50    --  -48.76  19.00   0.00   84
 14  ω   -117.00 -76.00   0.50    0.50    --  -48.76-125.00-150.00   82
 15  ω   -120.00 -76.00   0.50    0.50    --  -48.76-125.00 -90.00   88
 16  ω    -26.00  25.00   0.50    0.50    --  -48.76  19.00 -90.00  102
 17  ω    -24.00  12.00   0.50    0.50    --  -48.76  19.00 -30.00   72
 18  ω    -51.00 -25.00   0.50    1.50    --  -90.00  45.00 120.00   52
 19  ω    -47.00 -22.00   0.50    1.50    --  -90.00  45.00 150.00   50
 20  ω    141.00 167.00   0.50    1.50    --  111.50  45.00  30.00   52
 21  ω     79.00 105.00   0.50    1.50    --  111.50 -95.00 166.27   52
 22  ω    106.00 132.00   0.50    1.50    --  111.50  45.00  30.00   52
 23  ω     42.00  70.00   0.50    1.50    --  111.50 -61.00  60.00   56
 24  ω    102.00 178.00   0.50    1.50    --  111.50  45.00  90.00  152
 25  ω     41.00 107.00   0.50    1.50    --  111.50-102.00  -0.85  132
 26  ω     62.00 107.00   0.50    1.50    --  111.50-125.00-120.00   90
 27  ω     46.00  72.00   0.50    1.50    --  111.50 -87.00-167.66   52
 28  ω     74.00 104.00   0.50    1.50    --  111.50 -95.00 -30.00   60
 29  ω     48.00  77.00   0.50    1.50    --  111.50 -68.00 148.46   58
 30  ω     77.00 103.00   0.50    1.50    --  111.50 -95.00 150.00   52
 31  ω     40.00  71.00   0.50    1.50    --  111.50 -61.00-120.00   62
 32  ω     43.00  68.00   0.50    1.50    --  111.50 -77.00-120.00   50
 33  ω     42.00  72.00   0.50    1.50    --  111.50 -77.00  90.00   60
 34  ω     95.00 121.00   0.50    1.50    --  111.50 -87.00-167.66   52
 35  ω     84.00 109.00   0.50    1.50    --  111.50-125.00   0.00   50
 36  ω     94.00 137.00   0.50    1.50    --  111.50  70.00 -89.41   86
 37  ω    152.00 178.00   0.50    1.50    --  111.50  70.00 -89.41   52
 38  ω    102.00 154.00   0.50    1.50    --  111.50  30.00  90.00  104
 39  ω     58.00 107.00   0.50    1.50    --  111.50-110.00-107.52   98
 40  ω     48.00  74.00   0.50    1.50    --  111.50-125.00 -60.00   52
 41  ω     48.00  74.00   0.50    1.50    --  111.50 -81.00   2.67   52
 42  ω     90.00 135.00   0.50    1.50    --  111.50 -81.00   2.67   90
 43  ω    102.00 171.00   0.50    1.50    --  111.50  15.00   0.00  138
 44  ω     40.00  69.00   0.50    1.50    --  111.50 -95.00 -30.00   58
 45  ω     41.00  70.00   0.50    1.50    --  111.50 -61.00  90.00   58
 46  ω    141.00 167.00   0.50    1.50    --  111.50  77.00-150.00   52
 47  ω     91.00 117.00   0.50    1.50    --  111.50  77.00-150.00   52
 48  ω     73.00 108.00   0.50    1.50    --  111.50-109.00 -91.54   70
 49  ω     69.00 111.00   0.50    1.50    --  111.50-125.00  90.00   84
 50  ω     94.00 139.00   0.50    1.50    --  111.50  70.00-179.51   90
 51  ω    153.00 178.00   0.50    1.50    --  111.50  70.00-179.51   50
 52  ω     87.00 113.00   0.50    1.50    --  111.50 -85.00 137.79   52
 53  ω    145.00 171.00   0.50    1.50    --  111.50  91.00 -71.76   52
 54  ω     51.00  91.00   0.50    1.50    --  111.50 -77.00 -90.00   80
 55  ω     46.00  71.00   0.50    1.50    --  111.50 -61.00   0.00   50
 56  ω     69.00 105.00   0.50    1.50    --  111.50 -95.00-120.00   72
 57  ω     72.00  97.00   0.50    1.50    --  111.50 -95.00  30.00   50
 58  ω     46.00  71.00   0.50    1.50    --  111.50-125.00   0.00   50
 59  ω     42.00  67.00   0.50    1.50    --  111.50 -61.00 -30.00   50
 60  ω    133.00 178.00   0.50    1.50    --  111.50  45.00 120.00   90
 61  ω    114.00 147.00   0.50    1.50    --  111.50  61.00 -30.00   66
 62  ω    102.00 176.00   0.50    1.50    --  111.50  77.00 150.00  148
 63  ω     90.00 116.00   0.50    1.50    --  111.50 -85.00 -91.93   52
 64  ω     88.00 113.00   0.50    1.50    --  111.50 165.00  34.00   50
;
_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      0.0219006000
_diffrn_orient_matrix_UB_12      0.0714388000
_diffrn_orient_matrix_UB_13      -0.1307350000
_diffrn_orient_matrix_UB_21      -0.1022237000
_diffrn_orient_matrix_UB_22      0.1056803000
_diffrn_orient_matrix_UB_23      0.0206763000
_diffrn_orient_matrix_UB_31      0.1228770000
_diffrn_orient_matrix_UB_32      0.0385924000
_diffrn_orient_matrix_UB_33      0.0029212000
_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                5872
_reflns_number_total             6239
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (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         0.383
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         6239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1120P)²+0.6411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1665
_refine_ls_wR_factor_ref         0.1688
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B), C13(H13A,H13B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C16(H16), C17(H17), C19(H19), C18(H18), C20(H20), C24(H24),
 C25(H25), C26(H26), C27(H27), C28(H28), C31(H31), C32(H32), C33(H33), C34(H34),
  C35(H35)
2.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.48253(12) 0.57577(10) 0.74747(10) 0.0273(3) Uani 1 1 d . . . . .
C1 C 0.59511(17) 0.47913(15) 0.77949(14) 0.0263(3) Uani 1 1 d . . . . .
H1A H 0.557248 0.408079 0.828621 0.032 Uiso 1 1 calc R U . . .
H1B H 0.643063 0.490410 0.824839 0.032 Uiso 1 1 calc R U . . .
O2 O 0.63962(11) 0.43619(10) 0.61083(9) 0.0223(2) Uani 1 1 d . . . . .
C2 C 0.69936(16) 0.46418(14) 0.67553(13) 0.0224(3) Uani 1 1 d . . . . .
O3 O 0.55524(11) 0.66984(10) 0.49984(9) 0.0215(2) Uani 1 1 d . . . . .
C3 C 0.83346(16) 0.37198(14) 0.68762(14) 0.0261(3) Uani 1 1 d . . . . .
H3 H 0.877980 0.333940 0.750926 0.031 Uiso 1 1 calc R U . . .
O4 O 0.84144(11) 0.43198(10) 0.33178(10) 0.0245(3) Uani 1 1 d . . . . .
C4 C 0.87497(16) 0.35611(14) 0.59028(14) 0.0256(3) Uani 1 1 d . . . . .
H4 H 0.957731 0.306171 0.568519 0.031 Uiso 1 1 calc R U . . .
C5 C 0.76238(15) 0.43463(14) 0.52006(13) 0.0224(3) Uani 1 1 d . . . . .
O5 O 0.99191(16) 0.25928(13) 0.38096(13) 0.0458(4) Uani 1 1 d . . . . .
O6 O 0.53332(12) 0.77797(10) 0.27453(10) 0.0255(3) Uani 1 1 d . . . . .
C6 C 0.78506(15) 0.56129(13) 0.47040(13) 0.0202(3) Uani 1 1 d . . . . .
H6 H 0.883497 0.567969 0.427553 0.024 Uiso 1 1 calc R U . . .
C7 C 0.67462(15) 0.66530(13) 0.40750(13) 0.0205(3) Uani 1 1 d . . . . .
O7 O 0.52622(13) 0.75649(10) 0.12024(10) 0.0287(3) Uani 1 1 d . . . . .
O8 O 0.89785(12) 0.78191(10) 0.21557(10) 0.0261(3) Uani 1 1 d . . . . .
C8 C 0.72264(15) 0.77556(13) 0.37938(13) 0.0207(3) Uani 1 1 d . . . . .
O9 O 0.65953(14) 0.88969(12) 0.59243(11) 0.0336(3) Uani 1 1 d . . . . .
C9 C 0.68890(15) 0.78704(13) 0.47931(13) 0.0213(3) Uani 1 1 d . . . . .
C10 C 0.62392(15) 0.68301(14) 0.56834(13) 0.0213(3) Uani 1 1 d . . . . .
O10 O 0.80879(13) 0.93245(11) 0.42002(10) 0.0309(3) Uani 1 1 d . . . . .
C11 C 0.52807(17) 0.68268(14) 0.68080(14) 0.0256(3) Uani 1 1 d . . . . .
H11A H 0.578044 0.694455 0.724400 0.031 Uiso 1 1 calc R U . . .
H11B H 0.445712 0.747256 0.665717 0.031 Uiso 1 1 calc R U . . .
C12 C 0.74818(15) 0.57768(13) 0.58456(13) 0.0207(3) Uani 1 1 d . . . . .
H12 H 0.828840 0.589840 0.599670 0.025 Uiso 1 1 calc R U . . .
C13 C 0.74233(16) 0.39250(14) 0.44023(14) 0.0245(3) Uani 1 1 d . . . . .
H13A H 0.758821 0.306978 0.474432 0.029 Uiso 1 1 calc R U . . .
H13B H 0.645433 0.423813 0.427887 0.029 Uiso 1 1 calc R U . . .
C14 C 0.96242(17) 0.35800(15) 0.31375(15) 0.0267(3) Uani 1 1 d . . . . .
C15 C 1.05520(16) 0.41294(15) 0.20047(14) 0.0250(3) Uani 1 1 d . . . . .
C16 C 1.17979(18) 0.34355(16) 0.16676(15) 0.0299(4) Uani 1 1 d . . . . .
H16 H 1.206194 0.265428 0.217397 0.036 Uiso 1 1 calc R U . . .
C17 C 1.26544(18) 0.38851(18) 0.05915(16) 0.0332(4) Uani 1 1 d . . . . .
H17 H 1.348963 0.340343 0.035569 0.040 Uiso 1 1 calc R U . . .
C19 C 1.1070(2) 0.57307(16) 0.02139(17) 0.0353(4) Uani 1 1 d . . . . .
H19 H 1.083019 0.652149 -0.027937 0.042 Uiso 1 1 calc R U . . .
C18 C 1.22962(18) 0.50319(17) -0.01388(16) 0.0329(4) Uani 1 1 d . . . . .
H18 H 1.288242 0.533911 -0.087430 0.039 Uiso 1 1 calc R U . . .
C20 C 1.01924(18) 0.52845(16) 0.12794(16) 0.0308(4) Uani 1 1 d . . . . .
H20 H 0.935264 0.576520 0.151076 0.037 Uiso 1 1 calc R U . . .
C21 C 0.63114(16) 0.66861(14) 0.30961(13) 0.0231(3) Uani 1 1 d . . . . .
H21A H 0.712796 0.665213 0.245876 0.028 Uiso 1 1 calc R U . . .
H21B H 0.585816 0.603360 0.335403 0.028 Uiso 1 1 calc R U . . .
C22 C 0.48241(16) 0.80781(14) 0.18241(13) 0.0226(3) Uani 1 1 d . . . . .
C23 C 0.36715(16) 0.91259(14) 0.16871(14) 0.0236(3) Uani 1 1 d . . . . .
C24 C 0.32585(18) 0.97501(15) 0.06379(14) 0.0273(3) Uani 1 1 d . . . . .
H24 H 0.370296 0.950244 0.002481 0.033 Uiso 1 1 calc R U . . .
C25 C 0.21954(19) 1.07346(16) 0.04925(16) 0.0316(4) Uani 1 1 d . . . . .
H25 H 0.192126 1.116766 -0.022456 0.038 Uiso 1 1 calc R U . . .
C26 C 0.1538(2) 1.10840(18) 0.13878(18) 0.0362(4) Uani 1 1 d . . . . .
H26 H 0.080482 1.175361 0.128613 0.043 Uiso 1 1 calc R U . . .
C27 C 0.1938(2) 1.04652(19) 0.24385(17) 0.0368(4) Uani 1 1 d . . . . .
H27 H 0.147922 1.071174 0.305129 0.044 Uiso 1 1 calc R U . . .
C28 C 0.30074(18) 0.94875(16) 0.25898(15) 0.0297(4) Uani 1 1 d . . . . .
H28 H 0.328767 0.906498 0.330473 0.036 Uiso 1 1 calc R U . . .
C29 C 0.80250(15) 0.83899(14) 0.26315(13) 0.0213(3) Uani 1 1 d . . . . .
C30 C 0.76013(15) 0.96630(14) 0.20397(13) 0.0213(3) Uani 1 1 d . . . . .
C31 C 0.85957(17) 1.02687(15) 0.11674(14) 0.0250(3) Uani 1 1 d . . . . .
H31 H 0.953528 0.987177 0.100252 0.030 Uiso 1 1 calc R U . . .
C32 C 0.82146(19) 1.14449(16) 0.05436(15) 0.0306(4) Uani 1 1 d . . . . .
H32 H 0.889407 1.185807 -0.004200 0.037 Uiso 1 1 calc R U . . .
C33 C 0.6826(2) 1.20246(15) 0.07771(16) 0.0312(4) Uani 1 1 d . . . . .
H33 H 0.655839 1.283030 0.034270 0.037 Uiso 1 1 calc R U . . .
C34 C 0.58369(18) 1.14207(15) 0.16458(15) 0.0280(3) Uani 1 1 d . . . . .
H34 H 0.489325 1.181533 0.179903 0.034 Uiso 1 1 calc R U . . .
C35 C 0.62192(16) 1.02499(14) 0.22872(14) 0.0234(3) Uani 1 1 d . . . . .
H35 H 0.554658 0.984511 0.289366 0.028 Uiso 1 1 calc R U . . .
C36 C 0.71588(16) 0.87341(14) 0.50568(13) 0.0231(3) Uani 1 1 d . . . . .
C37 C 0.8304(3) 1.02808(19) 0.43094(18) 0.0423(5) Uani 1 1 d . . . . .
H37A H 0.878138 1.078052 0.356418 0.063 Uiso 1 1 calc R U . . .
H37B H 0.887927 0.998323 0.487567 0.063 Uiso 1 1 calc R U . . .
H37C H 0.739636 1.072735 0.456250 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
O1 C1 1.427(2) . ?
O1 C11 1.4269(19) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.508(2) . ?
O2 C2 1.4483(18) . ?
O2 C5 1.4421(17) . ?
C2 C3 1.519(2) . ?
C2 C12 1.555(2) . ?
O3 C7 1.4396(17) . ?
O3 C10 1.4354(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.330(2) . ?
O4 C13 1.4505(18) . ?
O4 C14 1.345(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.537(2) . ?
C5 C6 1.571(2) . ?
C5 C13 1.518(2) . ?
O5 C14 1.208(2) . ?
O6 C21 1.4437(19) . ?
O6 C22 1.3468(19) . ?
C6 H6 1.0000 . ?
C6 C7 1.568(2) . ?
C6 C12 1.556(2) . ?
C7 C8 1.549(2) . ?
C7 C21 1.507(2) . ?
O7 C22 1.205(2) . ?
O8 C29 1.226(2) . ?
C8 C9 1.341(2) . ?
C8 C29 1.488(2) . ?
O9 C36 1.204(2) . ?
C9 C10 1.533(2) . ?
C9 C36 1.482(2) . ?
C10 C11 1.507(2) . ?
C10 C12 1.546(2) . ?
O10 C36 1.3386(19) . ?
O10 C37 1.445(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.494(2) . ?
C15 C16 1.393(2) . ?
C15 C20 1.391(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(3) . ?
C19 H19 0.9500 . ?
C19 C18 1.392(3) . ?
C19 C20 1.389(2) . ?
C18 H18 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.491(2) . ?
C23 C24 1.395(2) . ?
C23 C28 1.397(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.378(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.391(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.387(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.483(2) . ?
C30 C31 1.397(2) . ?
C30 C35 1.400(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.383(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.399(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.391(2) . ?
C34 H34 0.9500 . ?
C34 C35 1.382(2) . ?
C35 H35 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 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
C11 O1 C1 112.74(12) . . ?
O1 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
O1 C1 C2 111.48(13) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
C5 O2 C2 96.49(11) . . ?
C1 C2 C3 121.12(14) . . ?
C1 C2 C12 112.93(13) . . ?
O2 C2 C1 112.41(12) . . ?
O2 C2 C3 101.23(12) . . ?
O2 C2 C12 102.31(12) . . ?
C3 C2 C12 104.66(12) . . ?
C10 O3 C7 97.28(10) . . ?
C2 C3 H3 127.5 . . ?
C4 C3 C2 105.00(14) . . ?
C4 C3 H3 127.5 . . ?
C14 O4 C13 118.17(13) . . ?
C3 C4 H4 126.8 . . ?
C3 C4 C5 106.32(14) . . ?
C5 C4 H4 126.8 . . ?
O2 C5 C4 100.78(12) . . ?
O2 C5 C6 101.56(12) . . ?
O2 C5 C13 111.02(12) . . ?
C4 C5 C6 106.31(12) . . ?
C13 C5 C4 115.96(14) . . ?
C13 C5 C6 118.83(13) . . ?
C22 O6 C21 117.17(12) . . ?
C5 C6 H6 112.4 . . ?
C7 C6 C5 119.31(12) . . ?
C7 C6 H6 112.4 . . ?
C12 C6 C5 99.51(11) . . ?
C12 C6 H6 112.4 . . ?
C12 C6 C7 99.20(11) . . ?
O3 C7 C6 103.08(11) . . ?
O3 C7 C8 99.92(11) . . ?
O3 C7 C21 110.51(11) . . ?
C8 C7 C6 105.47(11) . . ?
C21 C7 C6 121.41(13) . . ?
C21 C7 C8 113.87(13) . . ?
C9 C8 C7 105.65(13) . . ?
C9 C8 C29 132.47(14) . . ?
C29 C8 C7 121.57(13) . . ?
C8 C9 C10 105.08(13) . . ?
C8 C9 C36 129.71(14) . . ?
C36 C9 C10 125.04(13) . . ?
O3 C10 C9 100.57(11) . . ?
O3 C10 C11 111.89(12) . . ?
O3 C10 C12 102.42(12) . . ?
C9 C10 C12 104.97(11) . . ?
C11 C10 C9 122.08(13) . . ?
C11 C10 C12 112.60(13) . . ?
C36 O10 C37 115.95(14) . . ?
O1 C11 C10 110.65(13) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C2 C12 C6 102.49(12) . . ?
C2 C12 H12 113.0 . . ?
C6 C12 H12 113.0 . . ?
C10 C12 C2 111.30(12) . . ?
C10 C12 C6 103.08(12) . . ?
C10 C12 H12 113.0 . . ?
O4 C13 C5 108.10(12) . . ?
O4 C13 H13A 110.1 . . ?
O4 C13 H13B 110.1 . . ?
C5 C13 H13A 110.1 . . ?
C5 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
O4 C14 C15 111.67(14) . . ?
O5 C14 O4 123.98(15) . . ?
O5 C14 C15 124.35(15) . . ?
C16 C15 C14 117.80(15) . . ?
C20 C15 C14 122.30(15) . . ?
C20 C15 C16 119.88(16) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.07(17) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.31(16) . . ?
C18 C17 H17 119.8 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C20 C19 C18 120.74(18) . . ?
C17 C18 C19 119.43(17) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C15 C20 H20 120.2 . . ?
C19 C20 C15 119.54(16) . . ?
C19 C20 H20 120.2 . . ?
O6 C21 C7 103.93(12) . . ?
O6 C21 H21A 111.0 . . ?
O6 C21 H21B 111.0 . . ?
C7 C21 H21A 111.0 . . ?
C7 C21 H21B 111.0 . . ?
H21A C21 H21B 109.0 . . ?
O6 C22 C23 110.44(13) . . ?
O7 C22 O6 123.88(15) . . ?
O7 C22 C23 125.67(14) . . ?
C24 C23 C22 119.07(15) . . ?
C24 C23 C28 119.93(15) . . ?
C28 C23 C22 121.00(14) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.80(16) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.05(16) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C27 120.60(17) . . ?
C27 C26 H26 119.7 . . ?
C26 C27 H27 120.1 . . ?
C28 C27 C26 119.85(18) . . ?
C28 C27 H27 120.1 . . ?
C23 C28 H28 120.1 . . ?
C27 C28 C23 119.77(16) . . ?
C27 C28 H28 120.1 . . ?
O8 C29 C8 117.82(14) . . ?
O8 C29 C30 121.43(14) . . ?
C30 C29 C8 120.58(13) . . ?
C31 C30 C29 118.50(14) . . ?
C31 C30 C35 119.89(15) . . ?
C35 C30 C29 121.48(14) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 C30 120.13(15) . . ?
C32 C31 H31 119.9 . . ?
C31 C32 H32 120.1 . . ?
C31 C32 C33 119.83(16) . . ?
C33 C32 H32 120.1 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 C32 119.98(16) . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 119.8 . . ?
C35 C34 C33 120.39(16) . . ?
C35 C34 H34 119.8 . . ?
C30 C35 H35 120.1 . . ?
C34 C35 C30 119.75(15) . . ?
C34 C35 H35 120.1 . . ?
O9 C36 C9 124.21(14) . . ?
O9 C36 O10 124.31(15) . . ?
O10 C36 C9 111.48(13) . . ?
O10 C37 H37A 109.5 . . ?
O10 C37 H37B 109.5 . . ?
O10 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 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 C1 C2 O2 -64.55(17) . . . . ?
O1 C1 C2 C3 175.78(13) . . . . ?
O1 C1 C2 C12 50.59(17) . . . . ?
C1 O1 C11 C10 63.26(17) . . . . ?
C1 C2 C3 C4 159.65(14) . . . . ?
C1 C2 C12 C6 -151.78(13) . . . . ?
C1 C2 C12 C10 -42.20(17) . . . . ?
O2 C2 C3 C4 34.63(15) . . . . ?
O2 C2 C12 C6 -30.72(14) . . . . ?
O2 C2 C12 C10 78.86(14) . . . . ?
O2 C5 C6 C7 -67.01(16) . . . . ?
O2 C5 C6 C12 39.25(13) . . . . ?
O2 C5 C13 O4 159.26(12) . . . . ?
C2 O2 C5 C4 49.71(13) . . . . ?
C2 O2 C5 C6 -59.60(13) . . . . ?
C2 O2 C5 C13 173.10(13) . . . . ?
C2 C3 C4 C5 -2.63(16) . . . . ?
O3 C7 C8 C9 31.58(15) . . . . ?
O3 C7 C8 C29 -154.10(13) . . . . ?
O3 C7 C21 O6 60.88(15) . . . . ?
O3 C10 C11 O1 60.99(17) . . . . ?
O3 C10 C12 C2 -76.58(14) . . . . ?
O3 C10 C12 C6 32.62(13) . . . . ?
C3 C2 C12 C6 74.54(14) . . . . ?
C3 C2 C12 C10 -175.88(12) . . . . ?
C3 C4 C5 O2 -30.21(15) . . . . ?
C3 C4 C5 C6 75.35(15) . . . . ?
C3 C4 C5 C13 -150.12(13) . . . . ?
O4 C14 C15 C16 -175.35(14) . . . . ?
O4 C14 C15 C20 2.9(2) . . . . ?
C4 C5 C6 C7 -172.00(12) . . . . ?
C4 C5 C6 C12 -65.74(14) . . . . ?
C4 C5 C13 O4 -86.55(16) . . . . ?
C5 O2 C2 C1 177.37(13) . . . . ?
C5 O2 C2 C3 -51.95(13) . . . . ?
C5 O2 C2 C12 55.96(13) . . . . ?
C5 C6 C7 O3 71.09(16) . . . . ?
C5 C6 C7 C8 175.44(12) . . . . ?
C5 C6 C7 C21 -53.19(19) . . . . ?
C5 C6 C12 C2 -4.78(13) . . . . ?
C5 C6 C12 C10 -120.47(12) . . . . ?
O5 C14 C15 C16 4.5(3) . . . . ?
O5 C14 C15 C20 -177.27(18) . . . . ?
O6 C22 C23 C24 163.20(14) . . . . ?
O6 C22 C23 C28 -16.7(2) . . . . ?
C6 C5 C13 O4 42.10(18) . . . . ?
C6 C7 C8 C9 -75.09(14) . . . . ?
C6 C7 C8 C29 99.23(15) . . . . ?
C6 C7 C21 O6 -178.35(12) . . . . ?
C7 O3 C10 C9 52.85(13) . . . . ?
C7 O3 C10 C11 -176.05(13) . . . . ?
C7 O3 C10 C12 -55.22(13) . . . . ?
C7 C6 C12 C2 117.22(12) . . . . ?
C7 C6 C12 C10 1.54(13) . . . . ?
C7 C8 C9 C10 1.29(15) . . . . ?
C7 C8 C9 C36 176.71(15) . . . . ?
C7 C8 C29 O8 -43.7(2) . . . . ?
C7 C8 C29 C30 131.62(14) . . . . ?
O7 C22 C23 C24 -16.2(2) . . . . ?
O7 C22 C23 C28 163.94(16) . . . . ?
O8 C29 C30 C31 -26.3(2) . . . . ?
O8 C29 C30 C35 149.72(15) . . . . ?
C8 C7 C21 O6 -50.62(15) . . . . ?
C8 C9 C10 O3 -33.98(15) . . . . ?
C8 C9 C10 C11 -158.37(14) . . . . ?
C8 C9 C10 C12 72.06(14) . . . . ?
C8 C9 C36 O9 165.65(17) . . . . ?
C8 C9 C36 O10 -13.2(2) . . . . ?
C8 C29 C30 C31 158.55(14) . . . . ?
C8 C29 C30 C35 -25.5(2) . . . . ?
C9 C8 C29 O8 128.84(18) . . . . ?
C9 C8 C29 C30 -55.8(2) . . . . ?
C9 C10 C11 O1 -179.97(13) . . . . ?
C9 C10 C12 C2 178.75(12) . . . . ?
C9 C10 C12 C6 -72.06(13) . . . . ?
C10 O3 C7 C6 57.05(13) . . . . ?
C10 O3 C7 C8 -51.53(13) . . . . ?
C10 O3 C7 C21 -171.79(12) . . . . ?
C10 C9 C36 O9 -19.8(2) . . . . ?
C10 C9 C36 O10 161.40(14) . . . . ?
C11 O1 C1 C2 -61.81(17) . . . . ?
C11 C10 C12 C2 43.77(17) . . . . ?
C11 C10 C12 C6 152.97(12) . . . . ?
C12 C2 C3 C4 -71.42(15) . . . . ?
C12 C6 C7 O3 -35.34(13) . . . . ?
C12 C6 C7 C8 69.00(13) . . . . ?
C12 C6 C7 C21 -159.63(13) . . . . ?
C12 C10 C11 O1 -53.74(17) . . . . ?
C13 O4 C14 O5 2.4(2) . . . . ?
C13 O4 C14 C15 -177.76(13) . . . . ?
C13 C5 C6 C7 55.03(18) . . . . ?
C13 C5 C6 C12 161.29(13) . . . . ?
C14 O4 C13 C5 97.27(16) . . . . ?
C14 C15 C16 C17 175.93(16) . . . . ?
C14 C15 C20 C19 -177.06(17) . . . . ?
C15 C16 C17 C18 1.8(3) . . . . ?
C16 C15 C20 C19 1.2(3) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C18 C19 C20 C15 0.6(3) . . . . ?
C20 C15 C16 C17 -2.4(3) . . . . ?
C20 C19 C18 C17 -1.2(3) . . . . ?
C21 O6 C22 O7 -9.6(2) . . . . ?
C21 O6 C22 C23 171.06(12) . . . . ?
C21 C7 C8 C9 149.37(13) . . . . ?
C21 C7 C8 C29 -36.31(19) . . . . ?
C22 O6 C21 C7 176.24(12) . . . . ?
C22 C23 C24 C25 -179.38(14) . . . . ?
C22 C23 C28 C27 -179.97(16) . . . . ?
C23 C24 C25 C26 -0.9(3) . . . . ?
C24 C23 C28 C27 0.1(3) . . . . ?
C24 C25 C26 C27 0.6(3) . . . . ?
C25 C26 C27 C28 0.0(3) . . . . ?
C26 C27 C28 C23 -0.4(3) . . . . ?
C28 C23 C24 C25 0.5(2) . . . . ?
C29 C8 C9 C10 -172.15(16) . . . . ?
C29 C8 C9 C36 3.3(3) . . . . ?
C29 C30 C31 C32 175.62(14) . . . . ?
C29 C30 C35 C34 -174.17(14) . . . . ?
C30 C31 C32 C33 -0.9(3) . . . . ?
C31 C30 C35 C34 1.8(2) . . . . ?
C31 C32 C33 C34 0.9(3) . . . . ?
C32 C33 C34 C35 0.4(3) . . . . ?
C33 C34 C35 C30 -1.8(2) . . . . ?
C35 C30 C31 C32 -0.4(2) . . . . ?
C36 C9 C10 O3 150.32(14) . . . . ?
C36 C9 C10 C11 25.9(2) . . . . ?
C36 C9 C10 C12 -103.63(16) . . . . ?
C37 O10 C36 O9 -5.8(2) . . . . ?
C37 O10 C36 C9 173.01(15) . . . . ?

_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 4.400
_oxdiff_exptl_absorpt_empirical_full_min 0.525
####################################################################### 
# 
# 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_GA-416
_database_code_depnum_ccdc_archive 'CCDC 2207563'
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             
;
2022-09-15 deposited with the CCDC.	2023-01-02 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'Dimethyl 6-(acetoxymethyl)-7-(hydroxy(methoxy)methyl)-3a1,6a-dihydro- 1H,3H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isochromene-4,5-dicarboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H24 O11'
_chemical_formula_sum            'C21 H24 O11'
_chemical_formula_weight         452.40

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.5648(3)
_cell_length_b                   16.2470(5)
_cell_length_c                   12.4776(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.3080(10)
_cell_angle_gamma                90
_cell_volume                     2008.60(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9867
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      34.96
_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.510
_exptl_crystal_size_min          0.440
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6954
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_power             50
_diffrn_source_current           30
_diffrn_source_size              '0.6 mm, fine-focus'
_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            67798
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.145
_diffrn_reflns_theta_max         34.970
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8808
_reflns_number_gt                6915
_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, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_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)+(0.0347P)²+0.5667P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8808
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_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 0.17501(6) 0.59075(4) 0.71730(6) 0.01849(12) Uani 1 1 d . . . . .
H1 H 0.5237(16) 0.3463(10) 1.0506(14) 0.046(4) Uiso 1 1 d . . . . .
O2 O 0.04222(7) 0.53106(5) 0.80150(6) 0.02359(15) Uani 1 1 d . . . . .
O3 O 0.47538(6) 0.61592(4) 0.80729(5) 0.01324(11) Uani 1 1 d . . . . .
O4 O 0.38227(6) 0.33804(4) 0.80114(5) 0.01583(12) Uani 1 1 d . . . . .
O5 O 0.53792(6) 0.33023(4) 0.98508(5) 0.01704(12) Uani 1 1 d . . . . .
O6 O 0.63551(6) 0.49137(4) 0.93316(5) 0.01352(11) Uani 1 1 d . . . . .
O7 O 0.74570(6) 0.65895(4) 0.92829(5) 0.01766(12) Uani 1 1 d . . . . .
O8 O 0.62310(6) 0.70860(4) 0.55621(5) 0.01966(13) Uani 1 1 d . . . . .
O9 O 0.42103(7) 0.67110(5) 0.42997(5) 0.02339(15) Uani 1 1 d . . . . .
O10 O 0.16509(6) 0.63380(4) 0.47887(5) 0.01867(13) Uani 1 1 d . . . . .
O11 O 0.21947(8) 0.49926(4) 0.48825(7) 0.02909(17) Uani 1 1 d . . . . .
C1 C 0.39687(7) 0.55154(5) 0.73601(6) 0.01232(13) Uani 1 1 d . . . . .
C2 C 0.50402(8) 0.48312(5) 0.74126(6) 0.01237(13) Uani 1 1 d . . . . .
H2 H 0.4704(12) 0.4478(8) 0.6700(11) 0.020(3) Uiso 1 1 d . . . . .
C3 C 0.56195(8) 0.43021(5) 0.85213(6) 0.01274(13) Uani 1 1 d . . . . .
C4 C 0.67700(8) 0.37957(5) 0.83778(7) 0.01590(14) Uani 1 1 d . . . . .
H4 H 0.6697(12) 0.3206(8) 0.8129(11) 0.021(3) Uiso 1 1 d . . . . .
C5 C 0.78077(8) 0.43089(6) 0.85628(7) 0.01668(15) Uani 1 1 d . . . . .
H5 H 0.8715(13) 0.4214(8) 0.8492(11) 0.024(3) Uiso 1 1 d . . . . .
C6 C 0.72652(8) 0.51454(5) 0.87442(7) 0.01385(14) Uani 1 1 d . . . . .
C7 C 0.62813(8) 0.53849(5) 0.75339(6) 0.01289(13) Uani 1 1 d . . . . .
H7 H 0.6716(12) 0.5305(7) 0.6925(10) 0.015(3) Uiso 1 1 d . . . . .
C8 C 0.57186(8) 0.62634(5) 0.74985(6) 0.01269(13) Uani 1 1 d . . . . .
C9 C 0.47507(8) 0.63820(5) 0.62637(6) 0.01317(13) Uani 1 1 d . . . . .
C10 C 0.36709(8) 0.59195(5) 0.61848(6) 0.01324(13) Uani 1 1 d . . . . .
C11 C 0.27652(8) 0.52937(5) 0.76859(7) 0.01505(14) Uani 1 1 d . . . . .
H11A H 0.2410(13) 0.4724(8) 0.7377(11) 0.024(3) Uiso 1 1 d . . . . .
H11B H 0.3016(13) 0.5299(8) 0.8550(11) 0.022(3) Uiso 1 1 d . . . . .
C12 C 0.05950(8) 0.58363(5) 0.73938(7) 0.01642(15) Uani 1 1 d . . . . .
C13 C -0.04010(9) 0.64812(6) 0.67779(9) 0.02196(17) Uani 1 1 d . . . . .
H13A H -0.0174(19) 0.6713(12) 0.6160(17) 0.065(6) Uiso 1 1 d . . . . .
H13B H -0.038(2) 0.6928(14) 0.7295(19) 0.081(7) Uiso 1 1 d . . . . .
H13C H -0.1304(16) 0.6257(10) 0.6516(14) 0.044(4) Uiso 1 1 d . . . . .
C14 C 0.46527(8) 0.38319(5) 0.89573(6) 0.01343(13) Uani 1 1 d . . . . .
H14 H 0.4105(12) 0.4227(7) 0.9254(10) 0.018(3) Uiso 1 1 d . . . . .
C15 C 0.27389(9) 0.29704(6) 0.82252(8) 0.01957(16) Uani 1 1 d . . . . .
H15A H 0.2074(15) 0.3390(9) 0.8345(12) 0.035(4) Uiso 1 1 d . . . . .
H15B H 0.3088(13) 0.2603(9) 0.8932(12) 0.029(3) Uiso 1 1 d . . . . .
H15C H 0.2271(14) 0.2615(9) 0.7521(12) 0.030(3) Uiso 1 1 d . . . . .
C16 C 0.81844(8) 0.58396(6) 0.93419(7) 0.01743(15) Uani 1 1 d . . . . .
H16A H 0.8643(14) 0.5713(8) 1.0172(12) 0.030(3) Uiso 1 1 d . . . . .
H16B H 0.8916(13) 0.5908(8) 0.8982(11) 0.026(3) Uiso 1 1 d . . . . .
C17 C 0.67941(9) 0.68742(5) 0.81452(7) 0.01610(15) Uani 1 1 d . . . . .
H17A H 0.7454(13) 0.6950(8) 0.7732(11) 0.024(3) Uiso 1 1 d . . . . .
H17B H 0.6366(12) 0.7435(8) 0.8211(11) 0.022(3) Uiso 1 1 d . . . . .
C18 C 0.50039(8) 0.67443(5) 0.52674(7) 0.01441(14) Uani 1 1 d . . . . .
C19 C 0.65674(11) 0.74066(7) 0.46117(8) 0.0262(2) Uani 1 1 d . . . . .
H19A H 0.6380(15) 0.6995(10) 0.3982(14) 0.042(4) Uiso 1 1 d . . . . .
H19B H 0.7550(15) 0.7568(9) 0.4930(13) 0.038(4) Uiso 1 1 d . . . . .
H19C H 0.5959(17) 0.7904(11) 0.4283(14) 0.050(5) Uiso 1 1 d . . . . .
C20 C 0.24522(8) 0.56957(5) 0.51997(7) 0.01625(15) Uani 1 1 d . . . . .
C21 C 0.03532(10) 0.61490(7) 0.39495(9) 0.0281(2) Uani 1 1 d . . . . .
H21A H -0.0147(16) 0.6694(10) 0.3818(13) 0.044(4) Uiso 1 1 d . . . . .
H21B H -0.0158(16) 0.5727(10) 0.4252(13) 0.041(4) Uiso 1 1 d . . . . .
H21C H 0.0489(15) 0.5953(10) 0.3239(14) 0.042(4) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.3460(10) . ?
O1 C11 1.4414(10) . ?
O2 C12 1.2091(11) . ?
O3 C1 1.4356(10) . ?
O3 C8 1.4450(9) . ?
O4 C14 1.4076(10) . ?
O4 C15 1.4277(11) . ?
O5 C14 1.4066(10) . ?
O5 H1 0.919(17) . ?
O6 C3 1.4381(10) . ?
O6 C6 1.4466(10) . ?
O7 C17 1.4245(10) . ?
O7 C16 1.4287(11) . ?
O8 C18 1.3392(10) . ?
O8 C19 1.4478(11) . ?
O9 C18 1.2088(10) . ?
O10 C20 1.3294(11) . ?
O10 C21 1.4401(11) . ?
O11 C20 1.2086(11) . ?
C1 C11 1.5068(11) . ?
C1 C10 1.5364(11) . ?
C1 C2 1.5716(11) . ?
C2 C7 1.5537(11) . ?
C2 C3 1.5619(11) . ?
C2 H2 1.014(13) . ?
C3 C14 1.5194(11) . ?
C3 C4 1.5289(11) . ?
C4 C5 1.3322(12) . ?
C4 H4 1.002(13) . ?
C5 C6 1.5222(12) . ?
C5 H5 1.004(13) . ?
C6 C16 1.5062(12) . ?
C6 C7 1.5566(11) . ?
C7 C8 1.5408(11) . ?
C7 H7 1.023(12) . ?
C8 C17 1.5135(11) . ?
C8 C9 1.5372(11) . ?
C9 C10 1.3407(11) . ?
C9 C18 1.4813(11) . ?
C10 C20 1.4840(11) . ?
C11 H11A 1.023(13) . ?
C11 H11B 1.018(13) . ?
C12 C13 1.4948(12) . ?
C13 H13A 0.96(2) . ?
C13 H13B 0.97(2) . ?
C13 H13C 0.966(16) . ?
C14 H14 1.016(12) . ?
C15 H15A 1.027(15) . ?
C15 H15B 1.023(14) . ?
C15 H15C 1.023(14) . ?
C16 H16A 1.001(14) . ?
C16 H16B 1.026(13) . ?
C17 H17A 1.008(13) . ?
C17 H17B 1.033(13) . ?
C19 H19A 0.998(16) . ?
C19 H19B 1.008(15) . ?
C19 H19C 1.026(17) . ?
C21 H21A 1.015(16) . ?
C21 H21B 1.022(16) . ?
C21 H21C 0.998(16) . ?

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
C12 O1 C11 115.94(7) . . ?
C1 O3 C8 97.67(5) . . ?
C14 O4 C15 113.15(6) . . ?
C14 O5 H1 108.5(10) . . ?
C3 O6 C6 96.64(5) . . ?
C17 O7 C16 113.44(6) . . ?
C18 O8 C19 114.44(7) . . ?
C20 O10 C21 115.54(8) . . ?
O3 C1 C11 111.55(6) . . ?
O3 C1 C10 99.37(6) . . ?
C11 C1 C10 116.57(6) . . ?
O3 C1 C2 103.68(6) . . ?
C11 C1 C2 118.86(7) . . ?
C10 C1 C2 104.35(6) . . ?
C7 C2 C3 100.04(6) . . ?
C7 C2 C1 99.55(6) . . ?
C3 C2 C1 118.77(6) . . ?
C7 C2 H2 116.1(7) . . ?
C3 C2 H2 112.1(7) . . ?
C1 C2 H2 109.6(7) . . ?
O6 C3 C14 111.23(6) . . ?
O6 C3 C4 101.33(6) . . ?
C14 C3 C4 115.59(7) . . ?
O6 C3 C2 101.10(6) . . ?
C14 C3 C2 119.24(6) . . ?
C4 C3 C2 105.99(6) . . ?
C5 C4 C3 106.43(7) . . ?
C5 C4 H4 128.5(7) . . ?
C3 C4 H4 124.9(7) . . ?
C4 C5 C6 104.77(7) . . ?
C4 C5 H5 129.9(7) . . ?
C6 C5 H5 124.8(7) . . ?
O6 C6 C16 111.83(6) . . ?
O6 C6 C5 101.17(6) . . ?
C16 C6 C5 122.07(7) . . ?
O6 C6 C7 102.66(6) . . ?
C16 C6 C7 113.07(7) . . ?
C5 C6 C7 103.77(6) . . ?
C8 C7 C2 103.26(6) . . ?
C8 C7 C6 112.36(6) . . ?
C2 C7 C6 101.92(6) . . ?
C8 C7 H7 111.3(7) . . ?
C2 C7 H7 115.8(7) . . ?
C6 C7 H7 111.6(7) . . ?
O3 C8 C17 109.91(6) . . ?
O3 C8 C9 99.99(6) . . ?
C17 C8 C9 124.56(7) . . ?
O3 C8 C7 102.06(6) . . ?
C17 C8 C7 112.41(6) . . ?
C9 C8 C7 105.11(6) . . ?
C10 C9 C18 123.91(7) . . ?
C10 C9 C8 104.86(7) . . ?
C18 C9 C8 129.78(7) . . ?
C9 C10 C20 132.04(7) . . ?
C9 C10 C1 106.39(6) . . ?
C20 C10 C1 121.15(7) . . ?
O1 C11 C1 106.40(6) . . ?
O1 C11 H11A 109.9(7) . . ?
C1 C11 H11A 110.4(8) . . ?
O1 C11 H11B 110.2(7) . . ?
C1 C11 H11B 110.5(7) . . ?
H11A C11 H11B 109.5(10) . . ?
O2 C12 O1 122.76(8) . . ?
O2 C12 C13 126.08(8) . . ?
O1 C12 C13 111.16(7) . . ?
C12 C13 H13A 111.1(11) . . ?
C12 C13 H13B 109.6(13) . . ?
H13A C13 H13B 106.8(17) . . ?
C12 C13 H13C 110.2(10) . . ?
H13A C13 H13C 111.7(15) . . ?
H13B C13 H13C 107.4(15) . . ?
O5 C14 O4 110.83(7) . . ?
O5 C14 C3 109.98(6) . . ?
O4 C14 C3 105.21(6) . . ?
O5 C14 H14 108.7(7) . . ?
O4 C14 H14 111.5(7) . . ?
C3 C14 H14 110.6(7) . . ?
O4 C15 H15A 110.5(8) . . ?
O4 C15 H15B 111.2(8) . . ?
H15A C15 H15B 108.9(11) . . ?
O4 C15 H15C 106.4(8) . . ?
H15A C15 H15C 110.4(11) . . ?
H15B C15 H15C 109.5(11) . . ?
O7 C16 C6 111.73(7) . . ?
O7 C16 H16A 106.7(8) . . ?
C6 C16 H16A 110.8(8) . . ?
O7 C16 H16B 111.0(7) . . ?
C6 C16 H16B 108.6(7) . . ?
H16A C16 H16B 108.0(11) . . ?
O7 C17 C8 109.69(7) . . ?
O7 C17 H17A 111.2(7) . . ?
C8 C17 H17A 109.3(7) . . ?
O7 C17 H17B 106.5(7) . . ?
C8 C17 H17B 110.6(7) . . ?
H17A C17 H17B 109.5(10) . . ?
O9 C18 O8 124.24(8) . . ?
O9 C18 C9 123.77(8) . . ?
O8 C18 C9 111.96(7) . . ?
O8 C19 H19A 111.4(9) . . ?
O8 C19 H19B 106.4(9) . . ?
H19A C19 H19B 112.3(12) . . ?
O8 C19 H19C 108.3(9) . . ?
H19A C19 H19C 106.7(13) . . ?
H19B C19 H19C 111.6(12) . . ?
O11 C20 O10 125.08(8) . . ?
O11 C20 C10 122.33(8) . . ?
O10 C20 C10 112.36(7) . . ?
O10 C21 H21A 104.0(9) . . ?
O10 C21 H21B 111.5(9) . . ?
H21A C21 H21B 109.4(12) . . ?
O10 C21 H21C 108.7(9) . . ?
H21A C21 H21C 111.2(13) . . ?
H21B C21 H21C 111.8(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 O3 C1 C11 -175.75(6) . . . . ?
C8 O3 C1 C10 -52.21(6) . . . . ?
C8 O3 C1 C2 55.18(6) . . . . ?
O3 C1 C2 C7 -32.50(7) . . . . ?
C11 C1 C2 C7 -156.96(7) . . . . ?
C10 C1 C2 C7 71.11(7) . . . . ?
O3 C1 C2 C3 74.60(8) . . . . ?
C11 C1 C2 C3 -49.86(10) . . . . ?
C10 C1 C2 C3 178.21(6) . . . . ?
C6 O6 C3 C14 172.53(6) . . . . ?
C6 O6 C3 C4 49.13(7) . . . . ?
C6 O6 C3 C2 -59.87(6) . . . . ?
C7 C2 C3 O6 40.57(7) . . . . ?
C1 C2 C3 O6 -66.26(8) . . . . ?
C7 C2 C3 C14 162.75(7) . . . . ?
C1 C2 C3 C14 55.93(10) . . . . ?
C7 C2 C3 C4 -64.77(7) . . . . ?
C1 C2 C3 C4 -171.60(7) . . . . ?
O6 C3 C4 C5 -29.16(8) . . . . ?
C14 C3 C4 C5 -149.52(7) . . . . ?
C2 C3 C4 C5 76.01(8) . . . . ?
C3 C4 C5 C6 -3.58(8) . . . . ?
C3 O6 C6 C16 176.88(7) . . . . ?
C3 O6 C6 C5 -51.67(7) . . . . ?
C3 O6 C6 C7 55.37(7) . . . . ?
C4 C5 C6 O6 35.09(8) . . . . ?
C4 C5 C6 C16 159.90(8) . . . . ?
C4 C5 C6 C7 -71.07(8) . . . . ?
C3 C2 C7 C8 -123.13(6) . . . . ?
C1 C2 C7 C8 -1.43(7) . . . . ?
C3 C2 C7 C6 -6.44(7) . . . . ?
C1 C2 C7 C6 115.26(6) . . . . ?
O6 C6 C7 C8 80.72(7) . . . . ?
C16 C6 C7 C8 -39.93(9) . . . . ?
C5 C6 C7 C8 -174.24(6) . . . . ?
O6 C6 C7 C2 -29.17(7) . . . . ?
C16 C6 C7 C2 -149.83(7) . . . . ?
C5 C6 C7 C2 75.86(7) . . . . ?
C1 O3 C8 C17 -174.85(6) . . . . ?
C1 O3 C8 C9 52.58(7) . . . . ?
C1 O3 C8 C7 -55.37(6) . . . . ?
C2 C7 C8 O3 34.54(7) . . . . ?
C6 C7 C8 O3 -74.52(7) . . . . ?
C2 C7 C8 C17 152.24(6) . . . . ?
C6 C7 C8 C17 43.18(9) . . . . ?
C2 C7 C8 C9 -69.43(7) . . . . ?
C6 C7 C8 C9 -178.48(6) . . . . ?
O3 C8 C9 C10 -32.57(8) . . . . ?
C17 C8 C9 C10 -155.34(8) . . . . ?
C7 C8 C9 C10 72.93(8) . . . . ?
O3 C8 C9 C18 161.03(8) . . . . ?
C17 C8 C9 C18 38.25(13) . . . . ?
C7 C8 C9 C18 -93.47(9) . . . . ?
C18 C9 C10 C20 -5.16(14) . . . . ?
C8 C9 C10 C20 -172.59(8) . . . . ?
C18 C9 C10 C1 167.27(7) . . . . ?
C8 C9 C10 C1 -0.15(8) . . . . ?
O3 C1 C10 C9 33.01(8) . . . . ?
C11 C1 C10 C9 152.93(7) . . . . ?
C2 C1 C10 C9 -73.83(8) . . . . ?
O3 C1 C10 C20 -153.55(7) . . . . ?
C11 C1 C10 C20 -33.63(11) . . . . ?
C2 C1 C10 C20 99.61(8) . . . . ?
C12 O1 C11 C1 -177.91(7) . . . . ?
O3 C1 C11 O1 80.20(8) . . . . ?
C10 C1 C11 O1 -32.96(9) . . . . ?
C2 C1 C11 O1 -159.26(6) . . . . ?
C11 O1 C12 O2 2.53(12) . . . . ?
C11 O1 C12 C13 -177.49(7) . . . . ?
C15 O4 C14 O5 68.07(8) . . . . ?
C15 O4 C14 C3 -173.09(7) . . . . ?
O6 C3 C14 O5 -71.95(8) . . . . ?
C4 C3 C14 O5 42.87(9) . . . . ?
C2 C3 C14 O5 171.05(6) . . . . ?
O6 C3 C14 O4 168.65(6) . . . . ?
C4 C3 C14 O4 -76.53(8) . . . . ?
C2 C3 C14 O4 51.64(9) . . . . ?
C17 O7 C16 C6 -61.47(9) . . . . ?
O6 C6 C16 O7 -67.51(8) . . . . ?
C5 C6 C16 O7 172.68(7) . . . . ?
C7 C6 C16 O7 47.77(9) . . . . ?
C16 O7 C17 C8 64.29(9) . . . . ?
O3 C8 C17 O7 58.73(8) . . . . ?
C9 C8 C17 O7 176.99(7) . . . . ?
C7 C8 C17 O7 -54.21(9) . . . . ?
C19 O8 C18 O9 -1.38(13) . . . . ?
C19 O8 C18 C9 176.44(8) . . . . ?
C10 C9 C18 O9 6.03(14) . . . . ?
C8 C9 C18 O9 170.15(9) . . . . ?
C10 C9 C18 O8 -171.80(8) . . . . ?
C8 C9 C18 O8 -7.69(12) . . . . ?
C21 O10 C20 O11 3.77(13) . . . . ?
C21 O10 C20 C10 -170.86(8) . . . . ?
C9 C10 C20 O11 116.98(11) . . . . ?
C1 C10 C20 O11 -54.54(12) . . . . ?
C9 C10 C20 O10 -68.22(12) . . . . ?
C1 C10 C20 O10 120.26(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H1 O3 0.919(17) 1.873(17) 2.7839(8) 170.6(15) 3_667 yes

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_ga-465
_database_code_depnum_ccdc_archive 'CCDC 2207564'
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             
;
2022-09-15 deposited with the CCDC.	2023-01-02 downloaded from the CCDC.
;
_audit_creation_date             2021-11-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6394)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'Dimethyl 6,7-bis((benzoyloxy)methyl)-2-benzyl-2,3,3a1,6a-tetrahydro-1H,6H,7H- 3a,6:7,9a-diepoxybenzo[de]isoquinoline-4,5-dicarboxylate'
_chemical_formula_moiety         'C39 H35 N O10'
_chemical_formula_sum            'C39 H35 N O10'
_chemical_formula_weight         677.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C39 H35 N O10'
_chemical_oxdiff_usercomment     GA-465
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                   9.19560(10)
_cell_length_b                   33.6799(5)
_cell_length_c                   10.50800(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.8130(10)
_cell_angle_gamma                90
_cell_volume                     3224.19(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17610
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.3560
_cell_measurement_theta_min      2.6160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.836
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.106a (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    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            33004
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.693
_diffrn_reflns_theta_min         2.624
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -38.00   0.40    1.50    --  -48.51 -44.00 -72.00  205
  2  ω    -50.00  22.00   0.40    1.50    --  -48.51  44.00  78.00  180
  3  ω     38.00 120.00   0.40    1.50    --   48.51  44.00  78.00  205
  4  ω    -23.00  49.00   0.40    1.50    --   48.51 -44.00 -72.00  180
  5  ω   -161.00 -79.00   0.40    1.50    --  -90.00 -44.00 -72.00  205
  6  ω    -50.00 -20.00   0.40    1.50    --  -90.00  44.00  78.00   75
  7  ω    101.00 177.00   0.40    1.50    --  111.50  44.00  78.00  190
  8  ω   -120.00 -74.00   0.40    1.50    --  -48.51-125.00  90.00  115
  9  ω    -25.00  25.00   0.40    1.50    --   48.51 -19.00-180.00  125
 10  ω    -71.00 -19.00   0.40    1.50    --  -90.00  61.00-120.00  130
 11  ω     40.00 104.00   0.40    1.50    --  111.50 -77.00-180.00  160
 12  ω     40.00  70.00   0.40    1.50    --  111.50 -61.00 -90.00   75
 13  ω     40.00  70.00   0.40    1.50    --  111.50 -61.00  90.00   75
 14  ω     40.00  70.00   0.40    1.50    --  111.50 -61.00 -60.00   75
 15  ω     40.00 104.00   0.40    1.50    --  111.50 -95.00-180.00  160
 16  ω     40.00  70.00   0.40    1.50    --  111.50 -61.00 -30.00   75
 17  ω     40.00  70.00   0.40    1.50    --  111.50 -61.00-150.00   75
 18  ω    101.00 177.00   0.40    1.50    --  111.50  30.00 120.00  190
 19  ω    101.00 177.00   0.40    1.50    --  111.50  45.00 120.00  190
 20  ω     40.00 104.00   0.40    1.50    --  111.50 -95.00  60.00  160
 21  ω    101.00 177.00   0.40    1.50    --  111.50  45.00 150.00  190
 22  ω    101.00 177.00   0.40    1.50    --  111.50  15.00-150.00  190
 23  ω     40.00 104.00   0.40    1.50    --  111.50 -95.00 -30.00  160
 24  ω     95.00 177.00   0.40    1.50    --  111.50 125.00   0.00  205
 25  ω     95.00 177.00   0.40    1.50    --  111.50 125.00 -30.00  205
 26  ω     40.00 104.00   0.40    1.50    --  111.50 -77.00   0.00  160
 27  ω     27.00  63.00   0.40    1.50    --   48.51  77.00 -30.00   90
;
_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      -0.0110601000
_diffrn_orient_matrix_UB_12      -0.0251610000
_diffrn_orient_matrix_UB_13      0.1208231000
_diffrn_orient_matrix_UB_21      0.1687513000
_diffrn_orient_matrix_UB_22      -0.0013131000
_diffrn_orient_matrix_UB_23      0.0287575000
_diffrn_orient_matrix_UB_31      -0.0013911000
_diffrn_orient_matrix_UB_32      0.0381860000
_diffrn_orient_matrix_UB_33      0.0803937000
_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                6100
_reflns_number_total             6867
_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 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_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         0.391
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.00065(11)
_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   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         6867
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0640
_refine_ls_restrained_S_all      1.089
_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)+(0.0457P)²+6.5162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1588
_refine_ls_wR_factor_ref         0.1613
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C5(H5A,H5B), C13(H13A,H13B), C20(H20A,H20B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C23(H23),
 C24(H24), C25(H25), C26(H26), C27(H27), C31(H31), C32(H32), C33(H33), C34(H34),
  C35(H35)
2.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C39(H39A,H39B,H39C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N1 N 0.5667(2) 0.71440(6) 0.7907(2) 0.0241(4) Uani 1 1 d . . . . .
C1 C 0.6474(3) 0.68364(7) 0.8699(2) 0.0229(5) Uani 1 1 d . . . . .
H1A H 0.598818 0.678852 0.947012 0.027 Uiso 1 1 calc R U . . .
H1B H 0.748394 0.693102 0.899134 0.027 Uiso 1 1 calc R U . . .
O2 O 0.74639(17) 0.64753(5) 0.69678(15) 0.0199(3) Uani 1 1 d . . . . .
C2 C 0.6546(3) 0.64518(7) 0.7973(2) 0.0212(5) Uani 1 1 d . . . . .
O3 O 0.4393(2) 0.65250(5) 0.27008(16) 0.0252(4) Uani 1 1 d . . . . .
C3 C 0.5047(3) 0.63131(7) 0.7254(2) 0.0210(5) Uani 1 1 d . . . . .
H3 H 0.446608 0.615323 0.780908 0.025 Uiso 1 1 calc R U . . .
O4 O 0.3172(2) 0.59669(6) 0.20292(18) 0.0327(4) Uani 1 1 d . . . . .
C4 C 0.4164(3) 0.66616(7) 0.6581(2) 0.0224(5) Uani 1 1 d . . . . .
O5 O 0.95920(18) 0.58642(5) 0.62116(16) 0.0245(4) Uani 1 1 d . . . . .
C5 C 0.4159(3) 0.70205(8) 0.7431(3) 0.0273(5) Uani 1 1 d . . . . .
H5A H 0.363606 0.724086 0.694041 0.033 Uiso 1 1 calc R U . . .
H5B H 0.363154 0.695806 0.816665 0.033 Uiso 1 1 calc R U . . .
O6 O 1.0113(2) 0.54976(6) 0.45419(17) 0.0316(4) Uani 1 1 d . . . . .
C6 C 0.2740(3) 0.64705(7) 0.5967(2) 0.0250(5) Uani 1 1 d . . . . .
H6 H 0.179745 0.649494 0.623420 0.030 Uiso 1 1 calc R U . . .
O7 O 0.7381(2) 0.52183(6) 0.67018(17) 0.0312(4) Uani 1 1 d . . . . .
C7 C 0.3091(3) 0.62632(7) 0.4983(2) 0.0238(5) Uani 1 1 d . . . . .
H7 H 0.245566 0.610332 0.440627 0.029 Uiso 1 1 calc R U . . .
O8 O 0.8450(2) 0.52482(5) 0.87495(17) 0.0306(4) Uani 1 1 d . . . . .
C8 C 0.4732(3) 0.63340(7) 0.4965(2) 0.0226(5) Uani 1 1 d . . . . .
O9 O 0.6005(2) 0.60167(7) 1.05391(19) 0.0402(5) Uani 1 1 d . . . . .
C9 C 0.5494(3) 0.60712(7) 0.6110(2) 0.0208(5) Uani 1 1 d . . . . .
H9 H 0.509455 0.579472 0.608189 0.025 Uiso 1 1 calc R U . . .
O10 O 0.8442(2) 0.59280(6) 1.06760(16) 0.0288(4) Uani 1 1 d . . . . .
C10 C 0.7203(3) 0.60798(7) 0.6477(2) 0.0206(5) Uani 1 1 d . . . . .
C11 C 0.7502(3) 0.58360(7) 0.7728(2) 0.0210(5) Uani 1 1 d . . . . .
C12 C 0.7171(3) 0.60743(7) 0.8667(2) 0.0214(5) Uani 1 1 d . . . . .
C13 C 0.5711(3) 0.75192(8) 0.8630(3) 0.0275(5) Uani 1 1 d . . . . .
H13A H 0.557043 0.746339 0.952967 0.033 Uiso 1 1 calc R U . . .
H13B H 0.489891 0.769299 0.824829 0.033 Uiso 1 1 calc R U . . .
C14 C 0.7157(3) 0.77312(7) 0.8610(2) 0.0253(5) Uani 1 1 d . . . . .
C15 C 0.7652(3) 0.78108(8) 0.7445(3) 0.0333(6) Uani 1 1 d . . . . .
H15 H 0.706784 0.773363 0.666821 0.040 Uiso 1 1 calc R U . . .
C16 C 0.8979(4) 0.80001(9) 0.7392(3) 0.0379(7) Uani 1 1 d . . . . .
H16 H 0.929501 0.805263 0.658434 0.046 Uiso 1 1 calc R U . . .
O1 O 0.48988(19) 0.67283(5) 0.54721(16) 0.0226(4) Uani 1 1 d . . . . .
C17 C 0.9853(3) 0.81140(9) 0.8527(3) 0.0360(6) Uani 1 1 d . . . . .
H17 H 1.078085 0.823616 0.850515 0.043 Uiso 1 1 calc R U . . .
C18 C 0.9330(3) 0.80438(8) 0.9689(3) 0.0313(6) Uani 1 1 d . . . . .
H18 H 0.989867 0.812648 1.046713 0.038 Uiso 1 1 calc R U . . .
C19 C 0.8005(3) 0.78570(8) 0.9735(2) 0.0271(5) Uani 1 1 d . . . . .
H19 H 0.766935 0.781379 1.053914 0.033 Uiso 1 1 calc R U . . .
C20 C 0.5308(3) 0.63030(8) 0.3685(2) 0.0248(5) Uani 1 1 d . . . . .
H20A H 0.632405 0.640699 0.377283 0.030 Uiso 1 1 calc R U . . .
H20B H 0.533237 0.602059 0.342758 0.030 Uiso 1 1 calc R U . . .
C21 C 0.3377(3) 0.63163(8) 0.1925(2) 0.0242(5) Uani 1 1 d . . . . .
C22 C 0.2536(3) 0.65777(8) 0.0935(2) 0.0253(5) Uani 1 1 d . . . . .
C23 C 0.2773(3) 0.69827(9) 0.0879(3) 0.0346(6) Uani 1 1 d . . . . .
H23 H 0.352770 0.710175 0.146257 0.042 Uiso 1 1 calc R U . . .
C24 C 0.1922(4) 0.72169(9) -0.0020(3) 0.0373(7) Uani 1 1 d . . . . .
H24 H 0.208312 0.749523 -0.004326 0.045 Uiso 1 1 calc R U . . .
C25 C 0.0825(3) 0.70401(9) -0.0892(3) 0.0327(6) Uani 1 1 d . . . . .
H25 H 0.022647 0.719846 -0.150241 0.039 Uiso 1 1 calc R U . . .
C26 C 0.0619(3) 0.66370(9) -0.0860(3) 0.0321(6) Uani 1 1 d . . . . .
H26 H -0.009733 0.651555 -0.147500 0.039 Uiso 1 1 calc R U . . .
C27 C 0.1449(3) 0.64035(9) 0.0065(2) 0.0290(6) Uani 1 1 d . . . . .
H27 H 0.127101 0.612615 0.010134 0.035 Uiso 1 1 calc R U . . .
C28 C 0.8192(3) 0.59745(8) 0.5496(2) 0.0232(5) Uani 1 1 d . . . . .
H28A H 0.777540 0.575035 0.495536 0.028 Uiso 1 1 calc R U . . .
H28B H 0.830956 0.620474 0.493307 0.028 Uiso 1 1 calc R U . . .
C29 C 1.0404(3) 0.55989(7) 0.5652(2) 0.0233(5) Uani 1 1 d . . . . .
C30 C 1.1679(3) 0.54495(7) 0.6552(2) 0.0229(5) Uani 1 1 d . . . . .
C31 C 1.1933(3) 0.55707(9) 0.7833(2) 0.0304(6) Uani 1 1 d . . . . .
H31 H 1.127107 0.574824 0.815894 0.036 Uiso 1 1 calc R U . . .
C32 C 1.3157(3) 0.54308(10) 0.8630(3) 0.0366(7) Uani 1 1 d . . . . .
H32 H 1.333945 0.551583 0.949955 0.044 Uiso 1 1 calc R U . . .
C33 C 1.4110(3) 0.51676(9) 0.8157(3) 0.0359(6) Uani 1 1 d . . . . .
H33 H 1.494154 0.507092 0.870472 0.043 Uiso 1 1 calc R U . . .
C34 C 1.3852(3) 0.50442(9) 0.6881(3) 0.0330(6) Uani 1 1 d . . . . .
H34 H 1.450444 0.486269 0.656066 0.040 Uiso 1 1 calc R U . . .
C35 C 1.2641(3) 0.51865(8) 0.6078(3) 0.0287(6) Uani 1 1 d . . . . .
H35 H 1.246951 0.510442 0.520512 0.034 Uiso 1 1 calc R U . . .
C36 C 0.7767(3) 0.54072(7) 0.7672(2) 0.0222(5) Uani 1 1 d . . . . .
C37 C 0.8774(4) 0.48282(8) 0.8632(3) 0.0411(7) Uani 1 1 d . . . . .
H37A H 0.927922 0.472959 0.945274 0.062 Uiso 1 1 calc R U . . .
H37B H 0.940550 0.479112 0.796159 0.062 Uiso 1 1 calc R U . . .
H37C H 0.785689 0.468092 0.840349 0.062 Uiso 1 1 calc R U . . .
C38 C 0.7107(3) 0.59972(7) 1.0051(2) 0.0238(5) Uani 1 1 d . . . . .
C39 C 0.8527(3) 0.58726(9) 1.2053(2) 0.0350(6) Uani 1 1 d . . . . .
H39A H 0.955935 0.585974 1.243551 0.052 Uiso 1 1 calc R U . . .
H39B H 0.803291 0.562473 1.222791 0.052 Uiso 1 1 calc R U . . .
H39C H 0.804774 0.609594 1.242527 0.052 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
N1 C1 1.467(3) . ?
N1 C5 1.468(3) . ?
N1 C13 1.472(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.509(3) . ?
O2 C2 1.441(3) . ?
O2 C10 1.437(3) . ?
C2 C3 1.551(3) . ?
C2 C12 1.538(3) . ?
O3 C20 1.450(3) . ?
O3 C21 1.350(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.543(3) . ?
C3 C9 1.553(3) . ?
O4 C21 1.199(3) . ?
C4 C5 1.503(4) . ?
C4 C6 1.522(3) . ?
C4 O1 1.442(3) . ?
O5 C28 1.448(3) . ?
O5 C29 1.350(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
O6 C29 1.209(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.324(4) . ?
O7 C36 1.213(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.530(3) . ?
O8 C36 1.330(3) . ?
O8 C37 1.454(3) . ?
C8 C9 1.578(3) . ?
C8 O1 1.432(3) . ?
C8 C20 1.515(4) . ?
O9 C38 1.198(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.567(3) . ?
O10 C38 1.332(3) . ?
O10 C39 1.450(3) . ?
C10 C11 1.542(3) . ?
C10 C28 1.507(3) . ?
C11 C12 1.339(3) . ?
C11 C36 1.467(3) . ?
C12 C38 1.486(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.511(4) . ?
C14 C15 1.390(4) . ?
C14 C19 1.390(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.398(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.393(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.378(4) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.496(3) . ?
C22 C23 1.384(4) . ?
C22 C27 1.389(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.387(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.401(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.372(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.395(4) . ?
C27 H27 0.9500 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.491(3) . ?
C30 C31 1.395(4) . ?
C30 C35 1.391(4) . ?
C31 H31 0.9500 . ?
C31 C32 1.391(4) . ?
C32 H32 0.9500 . ?
C32 C33 1.385(4) . ?
C33 H33 0.9500 . ?
C33 C34 1.393(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.388(4) . ?
C35 H35 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 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 N1 C5 112.0(2) . . ?
C1 N1 C13 109.68(19) . . ?
C5 N1 C13 112.2(2) . . ?
N1 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
N1 C1 C2 111.86(19) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
C10 O2 C2 97.24(17) . . ?
C1 C2 C3 114.1(2) . . ?
C1 C2 C12 120.6(2) . . ?
O2 C2 C1 113.2(2) . . ?
O2 C2 C3 103.29(18) . . ?
O2 C2 C12 100.05(18) . . ?
C12 C2 C3 103.42(19) . . ?
C21 O3 C20 116.69(19) . . ?
C2 C3 H3 112.8 . . ?
C2 C3 C9 102.93(19) . . ?
C4 C3 C2 111.79(19) . . ?
C4 C3 H3 112.8 . . ?
C4 C3 C9 102.85(18) . . ?
C9 C3 H3 112.8 . . ?
C5 C4 C3 112.6(2) . . ?
C5 C4 C6 121.3(2) . . ?
C6 C4 C3 103.97(19) . . ?
O1 C4 C3 102.36(18) . . ?
O1 C4 C5 113.2(2) . . ?
O1 C4 C6 101.20(19) . . ?
C29 O5 C28 116.66(18) . . ?
N1 C5 C4 110.6(2) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C4 C6 H6 127.3 . . ?
C7 C6 C4 105.5(2) . . ?
C7 C6 H6 127.3 . . ?
C6 C7 H7 127.1 . . ?
C6 C7 C8 105.9(2) . . ?
C8 C7 H7 127.1 . . ?
C36 O8 C37 113.5(2) . . ?
C7 C8 C9 103.85(19) . . ?
O1 C8 C7 101.29(19) . . ?
O1 C8 C9 102.87(18) . . ?
O1 C8 C20 111.2(2) . . ?
C20 C8 C7 117.7(2) . . ?
C20 C8 C9 117.7(2) . . ?
C3 C9 C8 99.15(18) . . ?
C3 C9 H9 112.1 . . ?
C3 C9 C10 99.31(18) . . ?
C8 C9 H9 112.1 . . ?
C10 C9 C8 120.25(19) . . ?
C10 C9 H9 112.1 . . ?
C38 O10 C39 115.8(2) . . ?
O2 C10 C9 102.63(18) . . ?
O2 C10 C11 100.74(18) . . ?
O2 C10 C28 112.12(19) . . ?
C11 C10 C9 104.91(19) . . ?
C28 C10 C9 120.4(2) . . ?
C28 C10 C11 113.8(2) . . ?
C12 C11 C10 106.1(2) . . ?
C12 C11 C36 132.4(2) . . ?
C36 C11 C10 120.1(2) . . ?
C11 C12 C2 104.7(2) . . ?
C11 C12 C38 131.3(2) . . ?
C38 C12 C2 123.1(2) . . ?
N1 C13 H13A 109.4 . . ?
N1 C13 H13B 109.4 . . ?
N1 C13 C14 111.2(2) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 C19 118.5(3) . . ?
C19 C14 C13 121.7(2) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.4(3) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C8 O1 C4 96.77(17) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 C16 118.3(3) . . ?
C18 C17 H17 120.8 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.3(3) . . ?
C19 C18 H18 119.3 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
O3 C20 C8 111.0(2) . . ?
O3 C20 H20A 109.4 . . ?
O3 C20 H20B 109.4 . . ?
C8 C20 H20A 109.4 . . ?
C8 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
O3 C21 C22 111.3(2) . . ?
O4 C21 O3 124.1(2) . . ?
O4 C21 C22 124.6(2) . . ?
C23 C22 C21 122.7(2) . . ?
C23 C22 C27 119.5(2) . . ?
C27 C22 C21 117.8(2) . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.8(3) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.6(3) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.6(3) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 119.6 . . ?
C25 C26 C27 120.7(2) . . ?
C27 C26 H26 119.6 . . ?
C22 C27 C26 119.8(3) . . ?
C22 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
O5 C28 C10 106.35(18) . . ?
O5 C28 H28A 110.5 . . ?
O5 C28 H28B 110.5 . . ?
C10 C28 H28A 110.5 . . ?
C10 C28 H28B 110.5 . . ?
H28A C28 H28B 108.7 . . ?
O5 C29 C30 112.4(2) . . ?
O6 C29 O5 123.0(2) . . ?
O6 C29 C30 124.6(2) . . ?
C31 C30 C29 121.8(2) . . ?
C35 C30 C29 118.1(2) . . ?
C35 C30 C31 120.0(2) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 C30 119.9(3) . . ?
C32 C31 H31 120.1 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 120.0(3) . . ?
C33 C32 H32 120.0 . . ?
C32 C33 H33 119.9 . . ?
C32 C33 C34 120.2(3) . . ?
C34 C33 H33 119.9 . . ?
C33 C34 H34 120.0 . . ?
C35 C34 C33 120.0(3) . . ?
C35 C34 H34 120.0 . . ?
C30 C35 H35 120.1 . . ?
C34 C35 C30 119.9(3) . . ?
C34 C35 H35 120.1 . . ?
O7 C36 O8 123.7(2) . . ?
O7 C36 C11 121.2(2) . . ?
O8 C36 C11 115.1(2) . . ?
O8 C37 H37A 109.5 . . ?
O8 C37 H37B 109.5 . . ?
O8 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O9 C38 O10 125.1(2) . . ?
O9 C38 C12 123.9(2) . . ?
O10 C38 C12 110.9(2) . . ?
O10 C39 H39A 109.5 . . ?
O10 C39 H39B 109.5 . . ?
O10 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 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
N1 C1 C2 O2 69.4(3) . . . . ?
N1 C1 C2 C3 -48.3(3) . . . . ?
N1 C1 C2 C12 -172.3(2) . . . . ?
N1 C13 C14 C15 53.6(3) . . . . ?
N1 C13 C14 C19 -127.5(3) . . . . ?
C1 N1 C5 C4 -62.2(3) . . . . ?
C1 N1 C13 C14 79.6(3) . . . . ?
C1 C2 C3 C4 42.1(3) . . . . ?
C1 C2 C3 C9 151.8(2) . . . . ?
C1 C2 C12 C11 -161.1(2) . . . . ?
C1 C2 C12 C38 28.6(3) . . . . ?
O2 C2 C3 C4 -81.2(2) . . . . ?
O2 C2 C3 C9 28.6(2) . . . . ?
O2 C2 C12 C11 -36.4(2) . . . . ?
O2 C2 C12 C38 153.3(2) . . . . ?
O2 C10 C11 C12 28.7(2) . . . . ?
O2 C10 C11 C36 -163.1(2) . . . . ?
O2 C10 C28 O5 80.4(2) . . . . ?
C2 O2 C10 C9 57.80(19) . . . . ?
C2 O2 C10 C11 -50.30(19) . . . . ?
C2 O2 C10 C28 -171.64(18) . . . . ?
C2 C3 C4 C5 -45.6(3) . . . . ?
C2 C3 C4 C6 -178.7(2) . . . . ?
C2 C3 C4 O1 76.2(2) . . . . ?
C2 C3 C9 C8 -117.18(19) . . . . ?
C2 C3 C9 C10 5.7(2) . . . . ?
C2 C12 C38 O9 51.7(4) . . . . ?
C2 C12 C38 O10 -124.5(2) . . . . ?
O3 C21 C22 C23 -1.8(4) . . . . ?
O3 C21 C22 C27 -180.0(2) . . . . ?
C3 C2 C12 C11 70.0(2) . . . . ?
C3 C2 C12 C38 -100.3(3) . . . . ?
C3 C4 C5 N1 55.6(3) . . . . ?
C3 C4 C6 C7 -72.8(2) . . . . ?
C3 C4 O1 C8 56.3(2) . . . . ?
C3 C9 C10 O2 -38.8(2) . . . . ?
C3 C9 C10 C11 66.1(2) . . . . ?
C3 C9 C10 C28 -164.1(2) . . . . ?
O4 C21 C22 C23 177.6(3) . . . . ?
O4 C21 C22 C27 -0.6(4) . . . . ?
C4 C3 C9 C8 -0.9(2) . . . . ?
C4 C3 C9 C10 122.04(19) . . . . ?
C4 C6 C7 C8 -1.4(3) . . . . ?
O5 C29 C30 C31 1.8(3) . . . . ?
O5 C29 C30 C35 -177.3(2) . . . . ?
C5 N1 C1 C2 58.4(3) . . . . ?
C5 N1 C13 C14 -155.2(2) . . . . ?
C5 C4 C6 C7 159.3(2) . . . . ?
C5 C4 O1 C8 177.8(2) . . . . ?
O6 C29 C30 C31 -178.3(3) . . . . ?
O6 C29 C30 C35 2.6(4) . . . . ?
C6 C4 C5 N1 179.6(2) . . . . ?
C6 C4 O1 C8 -50.8(2) . . . . ?
C6 C7 C8 C9 75.4(2) . . . . ?
C6 C7 C8 O1 -31.0(2) . . . . ?
C6 C7 C8 C20 -152.4(2) . . . . ?
C7 C8 C9 C3 -69.8(2) . . . . ?
C7 C8 C9 C10 -176.3(2) . . . . ?
C7 C8 O1 C4 49.8(2) . . . . ?
C7 C8 C20 O3 47.8(3) . . . . ?
C8 C9 C10 O2 67.6(2) . . . . ?
C8 C9 C10 C11 172.5(2) . . . . ?
C8 C9 C10 C28 -57.8(3) . . . . ?
C9 C3 C4 C5 -155.4(2) . . . . ?
C9 C3 C4 C6 71.5(2) . . . . ?
C9 C3 C4 O1 -33.5(2) . . . . ?
C9 C8 O1 C4 -57.4(2) . . . . ?
C9 C8 C20 O3 173.32(19) . . . . ?
C9 C10 C11 C12 -77.6(2) . . . . ?
C9 C10 C11 C36 90.6(2) . . . . ?
C9 C10 C28 O5 -158.8(2) . . . . ?
C10 O2 C2 C1 -177.15(19) . . . . ?
C10 O2 C2 C3 -53.3(2) . . . . ?
C10 O2 C2 C12 53.21(19) . . . . ?
C10 C11 C12 C2 4.6(2) . . . . ?
C10 C11 C12 C38 173.8(2) . . . . ?
C10 C11 C36 O7 -20.0(4) . . . . ?
C10 C11 C36 O8 159.9(2) . . . . ?
C11 C10 C28 O5 -33.1(3) . . . . ?
C11 C12 C38 O9 -115.8(3) . . . . ?
C11 C12 C38 O10 68.0(4) . . . . ?
C12 C2 C3 C4 174.91(19) . . . . ?
C12 C2 C3 C9 -75.4(2) . . . . ?
C12 C11 C36 O7 144.6(3) . . . . ?
C12 C11 C36 O8 -35.5(4) . . . . ?
C13 N1 C1 C2 -176.3(2) . . . . ?
C13 N1 C5 C4 173.9(2) . . . . ?
C13 C14 C15 C16 -179.2(3) . . . . ?
C13 C14 C19 C18 178.9(2) . . . . ?
C14 C15 C16 C17 0.3(5) . . . . ?
C15 C14 C19 C18 -2.2(4) . . . . ?
C15 C16 C17 C18 -2.1(5) . . . . ?
C16 C17 C18 C19 1.8(4) . . . . ?
O1 C4 C5 N1 -59.9(3) . . . . ?
O1 C4 C6 C7 33.1(2) . . . . ?
O1 C8 C9 C3 35.5(2) . . . . ?
O1 C8 C9 C10 -71.0(3) . . . . ?
O1 C8 C20 O3 -68.4(2) . . . . ?
C17 C18 C19 C14 0.4(4) . . . . ?
C19 C14 C15 C16 1.9(4) . . . . ?
C20 O3 C21 O4 2.1(4) . . . . ?
C20 O3 C21 C22 -178.6(2) . . . . ?
C20 C8 C9 C3 158.1(2) . . . . ?
C20 C8 C9 C10 51.6(3) . . . . ?
C20 C8 O1 C4 175.67(19) . . . . ?
C21 O3 C20 C8 -97.8(2) . . . . ?
C21 C22 C23 C24 -177.1(3) . . . . ?
C21 C22 C27 C26 178.9(2) . . . . ?
C22 C23 C24 C25 -0.9(5) . . . . ?
C23 C22 C27 C26 0.6(4) . . . . ?
C23 C24 C25 C26 -1.0(4) . . . . ?
C24 C25 C26 C27 2.7(4) . . . . ?
C25 C26 C27 C22 -2.5(4) . . . . ?
C27 C22 C23 C24 1.1(4) . . . . ?
C28 O5 C29 O6 10.6(4) . . . . ?
C28 O5 C29 C30 -169.5(2) . . . . ?
C28 C10 C11 C12 148.9(2) . . . . ?
C28 C10 C11 C36 -42.9(3) . . . . ?
C29 O5 C28 C10 150.8(2) . . . . ?
C29 C30 C31 C32 -178.5(3) . . . . ?
C29 C30 C35 C34 179.2(2) . . . . ?
C30 C31 C32 C33 -0.9(4) . . . . ?
C31 C30 C35 C34 0.1(4) . . . . ?
C31 C32 C33 C34 0.4(5) . . . . ?
C32 C33 C34 C35 0.3(4) . . . . ?
C33 C34 C35 C30 -0.6(4) . . . . ?
C35 C30 C31 C32 0.6(4) . . . . ?
C36 C11 C12 C2 -161.6(2) . . . . ?
C36 C11 C12 C38 7.6(5) . . . . ?
C37 O8 C36 O7 3.6(4) . . . . ?
C37 O8 C36 C11 -176.3(2) . . . . ?
C39 O10 C38 O9 0.2(4) . . . . ?
C39 O10 C38 C12 176.4(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 1.410
_oxdiff_exptl_absorpt_empirical_full_min 0.766
