# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 2255492'
loop_
_audit_author_name
_audit_author_address
'Konstantin Lyssenko'
;Chemical Department MSU
Russia
;
_audit_update_record             
;
2023-04-11 deposited with the CCDC.	2023-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 O4'
_chemical_formula_sum            'C18 H16 O4'
_chemical_formula_weight         296.31

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                   8.7095(4)
_cell_length_b                   8.6086(4)
_cell_length_c                   19.3283(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.799(2)
_cell_angle_gamma                90
_cell_volume                     1445.99(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    2670
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      30.2


_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7650
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 Quest with Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13735
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.112
_diffrn_reflns_theta_max         28.991
_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             3843
_reflns_number_gt                2727
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+1.2524P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3843
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1263
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.25262(15) 0.90433(16) 0.51469(7) 0.0187(3) Uani 1 1 d . . . . .
C1 C 0.3089(2) 0.7152(2) 0.60318(9) 0.0122(3) Uani 1 1 d . . . . .
O2 O 0.15309(15) 0.93233(15) 0.61821(7) 0.0161(3) Uani 1 1 d . . . . .
C2 C 0.2339(2) 0.5801(2) 0.60779(9) 0.0124(3) Uani 1 1 d . . . . .
O3 O 0.00267(15) 0.66395(16) 0.54480(7) 0.0190(3) Uani 1 1 d . . . . .
C3 C 0.4714(2) 0.7426(2) 0.62911(9) 0.0124(3) Uani 1 1 d . . . . .
O4 O -0.00399(15) 0.45708(16) 0.61540(7) 0.0191(3) Uani 1 1 d . . . . .
C4 C 0.5729(2) 0.8217(2) 0.58857(10) 0.0149(4) Uani 1 1 d . . . . .
H4A H 0.539417 0.853948 0.543030 0.018 Uiso 1 1 calc R U . . .
C5 C 0.7218(2) 0.8537(2) 0.61415(11) 0.0185(4) Uani 1 1 d . . . . .
H5A H 0.790430 0.905816 0.585776 0.022 Uiso 1 1 calc R U . . .
C6 C 0.7712(2) 0.8100(2) 0.68075(11) 0.0214(4) Uani 1 1 d . . . . .
H6A H 0.873013 0.833134 0.698372 0.026 Uiso 1 1 calc R U . . .
C7 C 0.6709(2) 0.7321(2) 0.72191(10) 0.0200(4) Uani 1 1 d . . . . .
H7A H 0.704423 0.701900 0.767731 0.024 Uiso 1 1 calc R U . . .
C8 C 0.5226(2) 0.6984(2) 0.69624(10) 0.0162(4) Uani 1 1 d . . . . .
H8A H 0.454997 0.644730 0.724530 0.019 Uiso 1 1 calc R U . . .
C9 C 0.3129(2) 0.4347(2) 0.63233(9) 0.0127(4) Uani 1 1 d . . . . .
C10 C 0.2877(2) 0.3681(2) 0.69657(10) 0.0155(4) Uani 1 1 d . . . . .
H10A H 0.216741 0.414614 0.725572 0.019 Uiso 1 1 calc R U . . .
C11 C 0.3657(2) 0.2347(2) 0.71809(10) 0.0156(4) Uani 1 1 d . . . . .
H11A H 0.349867 0.191856 0.762333 0.019 Uiso 1 1 calc R U . . .
C12 C 0.4669(2) 0.1631(2) 0.67567(10) 0.0162(4) Uani 1 1 d . . . . .
H12A H 0.518599 0.070400 0.690348 0.019 Uiso 1 1 calc R U . . .
C13 C 0.4919(2) 0.2277(2) 0.61175(10) 0.0159(4) Uani 1 1 d . . . . .
H13A H 0.561131 0.179451 0.582414 0.019 Uiso 1 1 calc R U . . .
C14 C 0.4158(2) 0.3630(2) 0.59057(10) 0.0148(4) Uani 1 1 d . . . . .
H14A H 0.434387 0.407201 0.546878 0.018 Uiso 1 1 calc R U . . .
C15 C 0.2324(2) 0.8586(2) 0.57192(10) 0.0135(4) Uani 1 1 d . . . . .
C16 C 0.0852(2) 1.0792(2) 0.59478(11) 0.0198(4) Uani 1 1 d . . . . .
H16A H 0.028997 1.125012 0.632020 0.030 Uiso 1 1 calc R U . . .
H16B H 0.014208 1.061119 0.554110 0.030 Uiso 1 1 calc R U . . .
H16C H 0.166843 1.150416 0.582414 0.030 Uiso 1 1 calc R U . . .
C17 C 0.0661(2) 0.5738(2) 0.58486(9) 0.0143(4) Uani 1 1 d . . . . .
C18 C -0.1667(2) 0.4373(2) 0.59724(11) 0.0209(4) Uani 1 1 d . . . . .
H18A H -0.2161(8) 0.4022(17) 0.6364(6) 0.031 Uiso 1 1 calc R U . . .
H18B H -0.1806(3) 0.3636(16) 0.5612(8) 0.031 Uiso 1 1 calc R U . . .
H18C H -0.2097(8) 0.5334(14) 0.5823(8) 0.031 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 C15 1.198(2) . ?
C1 C2 1.340(2) . ?
C1 C3 1.489(2) . ?
C1 C15 1.510(2) . ?
O2 C15 1.327(2) . ?
O2 C16 1.455(2) . ?
C2 C9 1.490(2) . ?
C2 C17 1.500(2) . ?
O3 C17 1.204(2) . ?
C3 C8 1.397(3) . ?
C3 C4 1.397(3) . ?
O4 C17 1.333(2) . ?
O4 C18 1.448(2) . ?
C4 C5 1.385(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.382(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.392(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.383(3) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 C14 1.390(3) . ?
C9 C10 1.398(3) . ?
C10 C11 1.384(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.387(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.385(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 H18A 0.945(13) . ?
C18 H18B 0.945(13) . ?
C18 H18C 0.945(13) . ?

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
C2 C1 C3 124.89(16) . . ?
C2 C1 C15 122.16(16) . . ?
C3 C1 C15 112.93(15) . . ?
C15 O2 C16 115.10(15) . . ?
C1 C2 C9 122.25(16) . . ?
C1 C2 C17 118.78(16) . . ?
C9 C2 C17 118.93(15) . . ?
C8 C3 C4 118.63(16) . . ?
C8 C3 C1 120.50(16) . . ?
C4 C3 C1 120.75(16) . . ?
C17 O4 C18 116.78(15) . . ?
C5 C4 C3 120.60(17) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C6 C5 C4 120.30(18) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C7 119.71(18) . . ?
C5 C6 H6A 120.1 . . ?
C7 C6 H6A 120.1 . . ?
C8 C7 C6 120.13(18) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C7 C8 C3 120.63(18) . . ?
C7 C8 H8A 119.7 . . ?
C3 C8 H8A 119.7 . . ?
C14 C9 C10 118.60(16) . . ?
C14 C9 C2 119.35(16) . . ?
C10 C9 C2 122.05(16) . . ?
C11 C10 C9 120.28(18) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C10 C11 C12 120.65(18) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C13 C12 C11 119.47(17) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C12 C13 C14 119.97(18) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C13 C14 C9 121.01(17) . . ?
C13 C14 H14A 119.5 . . ?
C9 C14 H14A 119.5 . . ?
O1 C15 O2 125.46(17) . . ?
O1 C15 C1 123.37(17) . . ?
O2 C15 C1 110.90(15) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O4 124.51(17) . . ?
O3 C17 C2 124.25(17) . . ?
O4 C17 C2 111.22(15) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C3 C1 C2 C9 -7.6(3) . . . . ?
C15 C1 C2 C9 174.00(16) . . . . ?
C3 C1 C2 C17 174.76(16) . . . . ?
C15 C1 C2 C17 -3.6(3) . . . . ?
C2 C1 C3 C8 -49.2(3) . . . . ?
C15 C1 C3 C8 129.25(18) . . . . ?
C2 C1 C3 C4 134.9(2) . . . . ?
C15 C1 C3 C4 -46.6(2) . . . . ?
C8 C3 C4 C5 0.9(3) . . . . ?
C1 C3 C4 C5 176.84(17) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C3 -0.3(3) . . . . ?
C4 C3 C8 C7 -0.2(3) . . . . ?
C1 C3 C8 C7 -176.10(18) . . . . ?
C1 C2 C9 C14 -70.1(2) . . . . ?
C17 C2 C9 C14 107.4(2) . . . . ?
C1 C2 C9 C10 109.4(2) . . . . ?
C17 C2 C9 C10 -73.0(2) . . . . ?
C14 C9 C10 C11 0.9(3) . . . . ?
C2 C9 C10 C11 -178.65(17) . . . . ?
C9 C10 C11 C12 -1.6(3) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C9 -0.7(3) . . . . ?
C10 C9 C14 C13 0.3(3) . . . . ?
C2 C9 C14 C13 179.80(16) . . . . ?
C16 O2 C15 O1 1.0(3) . . . . ?
C16 O2 C15 C1 175.18(14) . . . . ?
C2 C1 C15 O1 -102.7(2) . . . . ?
C3 C1 C15 O1 78.7(2) . . . . ?
C2 C1 C15 O2 82.9(2) . . . . ?
C3 C1 C15 O2 -95.60(18) . . . . ?
C18 O4 C17 O3 1.4(3) . . . . ?
C18 O4 C17 C2 -179.53(16) . . . . ?
C1 C2 C17 O3 22.6(3) . . . . ?
C9 C2 C17 O3 -155.04(18) . . . . ?
C1 C2 C17 O4 -156.40(17) . . . . ?
C9 C2 C17 O4 25.9(2) . . . . ?

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 2255493'
loop_
_audit_author_name
_audit_author_address
'Konstantin Lyssenko'
;Chemical Department MSU
Russia
;
_audit_update_record             
;
2023-04-11 deposited with the CCDC.	2023-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 O5'
_chemical_formula_sum            'C20 H18 O5'
_chemical_formula_weight         338.34

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

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

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

_cell_length_a                   7.3855(18)
_cell_length_b                   10.729(3)
_cell_length_c                   12.101(4)
_cell_angle_alpha                65.688(10)
_cell_angle_beta                 78.414(11)
_cell_angle_gamma                71.301(9)
_cell_volume                     825.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    1936
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      31.23

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7650
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 Quest with Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8082
_diffrn_reflns_av_unetI/netI     0.0749
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.853
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4343
_reflns_number_gt                3137
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0552P)²+0.3679P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4343
_refine_ls_number_parameters     281
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.1743
_refine_ls_wR_factor_gt          0.1592
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

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 -0.0828(2) 0.3552(2) 0.89235(15) 0.0618(5) Uani 1 1 d . . . . .
O2 O 0.2205(2) 0.29066(15) 0.93839(12) 0.0406(3) Uani 1 1 d . . . . .
O3 O 0.5248(2) 0.03732(19) 0.81589(18) 0.0666(6) Uani 1 1 d . . . . .
O4 O 0.21580(19) 0.05990(14) 0.87556(12) 0.0373(3) Uani 1 1 d . . . . .
C1 C 0.2993(2) 0.24923(19) 0.70648(16) 0.0306(4) Uani 1 1 d . . . . .
C2 C 0.1722(2) 0.3577(2) 0.73473(16) 0.0306(4) Uani 1 1 d . . . . .
C3 C 0.1215(2) 0.49841(19) 0.64541(17) 0.0315(4) Uani 1 1 d . . . . .
C8 C 0.2065(3) 0.5253(2) 0.52511(17) 0.0352(4) Uani 1 1 d . . . . .
C9 C 0.3326(3) 0.4091(2) 0.49296(17) 0.0355(4) Uani 1 1 d . . . . .
C14 C 0.3777(2) 0.2715(2) 0.58374(17) 0.0330(4) Uani 1 1 d . . . . .
C17 C 0.0857(3) 0.3339(2) 0.86212(18) 0.0385(4) Uani 1 1 d . . . . .
C18 C 0.1497(4) 0.2625(3) 1.0646(2) 0.0645(8) Uani 1 1 d . . . . .
H18A H 0.2558(19) 0.233(2) 1.1131(9) 0.097 Uiso 1 1 calc R U . . .
H18B H 0.085(3) 0.188(2) 1.0927(8) 0.097 Uiso 1 1 calc R U . . .
H18C H 0.061(3) 0.3476(16) 1.0719(4) 0.097 Uiso 1 1 calc R U . . .
C19 C 0.3610(3) 0.1057(2) 0.80352(19) 0.0395(4) Uani 1 1 d . . . . .
C20 C 0.2686(4) -0.0779(2) 0.9719(2) 0.0538(6) Uani 1 1 d . . . . .
H20A H 0.1561(19) -0.0998(10) 1.0212(13) 0.081 Uiso 1 1 calc R U . . .
H20B H 0.354(3) -0.0768(6) 1.0208(13) 0.081 Uiso 1 1 calc R U . . .
H20C H 0.330(3) -0.1481(12) 0.9373(6) 0.081 Uiso 1 1 calc R U . . .
C4 C 0.0071(11) 0.6173(10) 0.6611(5) 0.0303(10) Uani 0.5898(18) 1 d . . P A 1
H4A H -0.052978 0.608351 0.740188 0.036 Uiso 0.5898(18) 1 calc R U P A 1
C5 C -0.0291(6) 0.7511(5) 0.5707(4) 0.0317(8) Uani 0.5898(18) 1 d . . P A 1
H5A H -0.115907 0.829049 0.588161 0.038 Uiso 0.5898(18) 1 calc R U P A 1
C6 C 0.0614(5) 0.7725(4) 0.4536(3) 0.0286(7) Uani 0.5898(18) 1 d D . P A 1
C7 C 0.1787(7) 0.6574(5) 0.4291(4) 0.0269(7) Uani 0.5898(18) 1 d . . P A 1
H7A H 0.238786 0.666890 0.349964 0.032 Uiso 0.5898(18) 1 calc R U P A 1
C11 C 0.5348(6) 0.2918(5) 0.3503(3) 0.0300(8) Uani 0.5898(18) 1 d D . P A 1
C10 C 0.4221(7) 0.4100(4) 0.3736(5) 0.0284(8) Uani 0.5898(18) 1 d . . P A 1
H10A H 0.401161 0.498607 0.307005 0.034 Uiso 0.5898(18) 1 calc R U P A 1
C12 C 0.5695(8) 0.1588(4) 0.4445(4) 0.0336(9) Uani 0.5898(18) 1 d . . P A 1
H12A H 0.641870 0.075102 0.430462 0.040 Uiso 0.5898(18) 1 calc R U P A 1
C13 C 0.494(3) 0.156(2) 0.5575(18) 0.040(2) Uani 0.5898(18) 1 d . . P A 1
H13A H 0.523073 0.066937 0.623599 0.048 Uiso 0.5898(18) 1 calc R U P A 1
O5 O 0.6137(3) 0.2951(3) 0.2375(2) 0.0386(4) Uani 0.5898(18) 1 d D . P A 1
C15 C 0.5788(6) 0.4297(4) 0.1384(4) 0.0434(8) Uani 0.5898(18) 1 d D . P A 1
H15A H 0.637(4) 0.4159(6) 0.059(2) 0.065 Uiso 0.5898(18) 1 calc R U P A 1
H15B H 0.640(4) 0.495(2) 0.1516(13) 0.065 Uiso 0.5898(18) 1 calc R U P A 1
H15C H 0.435(4) 0.4741(18) 0.1341(16) 0.065 Uiso 0.5898(18) 1 calc R U P A 1
C16 C 0.0263(6) 0.9199(4) 0.3564(4) 0.0392(7) Uani 0.5898(18) 1 d D . P A 1
H16A H 0.128(3) 0.9229(9) 0.293(2) 0.059 Uiso 0.5898(18) 1 calc R U P A 1
H16B H 0.021(4) 0.9864(18) 0.3912(12) 0.059 Uiso 0.5898(18) 1 calc R U P A 1
H16C H -0.093(4) 0.9436(13) 0.323(2) 0.059 Uiso 0.5898(18) 1 calc R U P A 1
C4' C -0.0220(19) 0.6064(16) 0.6947(8) 0.0303(10) Uani 0.4102(18) 1 d . . P A 2
H4'A H -0.077682 0.578170 0.776090 0.036 Uiso 0.4102(18) 1 calc R U P A 2
C5' C -0.0656(9) 0.7425(8) 0.6179(6) 0.0317(8) Uani 0.4102(18) 1 d . . P A 2
H5'A H -0.149447 0.813483 0.645766 0.038 Uiso 0.4102(18) 1 calc R U P A 2
C6' C 0.0117(8) 0.7803(5) 0.4974(6) 0.0286(7) Uani 0.4102(18) 1 d D . P A 2
C7' C 0.1379(11) 0.6813(9) 0.4564(7) 0.0269(7) Uani 0.4102(18) 1 d . . P A 2
H7'A H 0.188416 0.715755 0.374134 0.032 Uiso 0.4102(18) 1 calc R U P A 2
C10' C 0.3875(12) 0.4588(6) 0.3703(9) 0.0284(8) Uani 0.4102(18) 1 d . . P A 2
H10B H 0.347857 0.555660 0.318330 0.034 Uiso 0.4102(18) 1 calc R U P A 2
C11' C 0.5047(9) 0.3551(6) 0.3306(5) 0.0300(8) Uani 0.4102(18) 1 d D . P A 2
C12' C 0.5573(12) 0.2146(7) 0.4133(8) 0.0336(9) Uani 0.4102(18) 1 d . . P A 2
H12B H 0.643958 0.147443 0.382115 0.040 Uiso 0.4102(18) 1 calc R U P A 2
C13' C 0.497(4) 0.163(3) 0.535(2) 0.050(6) Uani 0.4102(18) 1 d . . P A 2
H13B H 0.530296 0.065082 0.584225 0.060 Uiso 0.4102(18) 1 calc R U P A 2
O5' O -0.0483(5) 0.9214(3) 0.4291(3) 0.0386(4) Uani 0.4102(18) 1 d D . P A 2
C15' C 0.0332(10) 0.9687(7) 0.3061(4) 0.0434(8) Uani 0.4102(18) 1 d D . P A 2
H15D H -0.028(5) 1.072(4) 0.264(2) 0.065 Uiso 0.4102(18) 1 calc R U P A 2
H15E H 0.010(5) 0.914(3) 0.263(2) 0.065 Uiso 0.4102(18) 1 calc R U P A 2
H15F H 0.174(5) 0.953(4) 0.3057(4) 0.065 Uiso 0.4102(18) 1 calc R U P A 2
C16' C 0.5786(8) 0.3893(7) 0.1986(5) 0.0392(7) Uani 0.4102(18) 1 d D . P A 2
H16D H 0.566(5) 0.492(4) 0.1582(17) 0.059 Uiso 0.4102(18) 1 calc R U P A 2
H16E H 0.504(5) 0.361(4) 0.1584(18) 0.059 Uiso 0.4102(18) 1 calc R U P A 2
H16F H 0.714(5) 0.337(4) 0.1932(5) 0.059 Uiso 0.4102(18) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.199(2) . ?
O2 C17 1.333(2) . ?
O2 C18 1.448(3) . ?
O3 C19 1.199(2) . ?
O4 C19 1.327(2) . ?
O4 C20 1.446(2) . ?
C1 C2 1.360(2) . ?
C1 C14 1.432(3) . ?
C1 C19 1.495(3) . ?
C2 C3 1.430(3) . ?
C2 C17 1.495(3) . ?
C3 C4 1.350(9) . ?
C3 C8 1.414(3) . ?
C3 C4' 1.532(12) . ?
C8 C7 1.398(5) . ?
C8 C9 1.443(3) . ?
C8 C7' 1.494(9) . ?
C9 C10' 1.377(10) . ?
C9 C14 1.412(3) . ?
C9 C10 1.460(6) . ?
C14 C13 1.38(2) . ?
C14 C13' 1.47(3) . ?
C18 H18A 0.965(17) . ?
C18 H18B 0.965(17) . ?
C18 H18C 0.965(17) . ?
C20 H20A 0.955(16) . ?
C20 H20B 0.955(16) . ?
C20 H20C 0.955(16) . ?
C4 C5 1.381(10) . ?
C4 H4A 0.9500 . ?
C5 C6 1.400(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.370(4) . ?
C6 C16 1.509(5) . ?
C7 H7A 0.9500 . ?
C11 O5 1.363(4) . ?
C11 C10 1.380(5) . ?
C11 C12 1.394(5) . ?
C10 H10A 0.9500 . ?
C12 C13 1.36(2) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
O5 C15 1.432(4) . ?
C15 H15A 1.02(3) . ?
C15 H15B 1.02(3) . ?
C15 H15C 1.02(3) . ?
C16 H16A 0.95(3) . ?
C16 H16B 0.95(2) . ?
C16 H16C 0.95(3) . ?
C4' C5' 1.342(17) . ?
C4' H4'A 0.9500 . ?
C5' C6' 1.394(7) . ?
C5' H5'A 0.9500 . ?
C6' C7' 1.362(7) . ?
C6' O5' 1.363(4) . ?
C7' H7'A 0.9500 . ?
C10' C11' 1.369(6) . ?
C10' H10B 0.9500 . ?
C11' C12' 1.402(7) . ?
C11' C16' 1.510(5) . ?
C12' C13' 1.38(3) . ?
C12' H12B 0.9500 . ?
C13' H13B 0.9500 . ?
O5' C15' 1.431(4) . ?
C15' H15D 1.00(4) . ?
C15' H15E 1.00(4) . ?
C15' H15F 1.00(4) . ?
C16' H16D 0.98(4) . ?
C16' H16E 0.98(4) . ?
C16' H16F 0.98(4) . ?

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
C17 O2 C18 114.87(18) . . ?
C19 O4 C20 115.38(16) . . ?
C2 C1 C14 120.46(17) . . ?
C2 C1 C19 120.42(17) . . ?
C14 C1 C19 119.12(16) . . ?
C1 C2 C3 121.56(16) . . ?
C1 C2 C17 120.64(17) . . ?
C3 C2 C17 117.78(16) . . ?
C4 C3 C8 112.5(3) . . ?
C4 C3 C2 128.3(3) . . ?
C8 C3 C2 119.07(16) . . ?
C8 C3 C4' 127.0(5) . . ?
C2 C3 C4' 114.0(5) . . ?
C7 C8 C3 126.0(2) . . ?
C7 C8 C9 114.4(2) . . ?
C3 C8 C9 119.56(17) . . ?
C3 C8 C7' 106.7(3) . . ?
C9 C8 C7' 133.8(3) . . ?
C10' C9 C14 131.3(3) . . ?
C10' C9 C8 109.2(3) . . ?
C14 C9 C8 119.43(16) . . ?
C14 C9 C10 111.7(2) . . ?
C8 C9 C10 128.9(2) . . ?
C13 C14 C9 121.9(8) . . ?
C13 C14 C1 118.4(8) . . ?
C9 C14 C1 119.70(17) . . ?
C9 C14 C13' 112.8(11) . . ?
C1 C14 C13' 127.4(11) . . ?
O1 C17 O2 123.79(18) . . ?
O1 C17 C2 125.08(18) . . ?
O2 C17 C2 111.09(16) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 O4 122.68(19) . . ?
O3 C19 C1 124.00(18) . . ?
O4 C19 C1 113.33(15) . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 C4 C5 124.8(3) . . ?
C3 C4 H4A 117.6 . . ?
C5 C4 H4A 117.6 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C7 C6 C5 118.7(3) . . ?
C7 C6 C16 121.2(4) . . ?
C5 C6 C16 120.1(3) . . ?
C6 C7 C8 117.4(3) . . ?
C6 C7 H7A 121.3 . . ?
C8 C7 H7A 121.3 . . ?
O5 C11 C10 123.8(4) . . ?
O5 C11 C12 116.2(4) . . ?
C10 C11 C12 120.0(4) . . ?
C11 C10 C9 124.9(4) . . ?
C11 C10 H10A 117.5 . . ?
C9 C10 H10A 117.5 . . ?
C13 C12 C11 116.3(9) . . ?
C13 C12 H12A 121.9 . . ?
C11 C12 H12A 121.8 . . ?
C12 C13 C14 125.1(15) . . ?
C12 C13 H13A 117.4 . . ?
C14 C13 H13A 117.5 . . ?
C11 O5 C15 117.6(3) . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6 C16 H16A 109.5 . . ?
C6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5' C4' C3 117.1(5) . . ?
C5' C4' H4'A 121.4 . . ?
C3 C4' H4'A 121.4 . . ?
C4' C5' C6' 120.3(6) . . ?
C4' C5' H5'A 119.8 . . ?
C6' C5' H5'A 119.8 . . ?
C7' C6' O5' 125.0(6) . . ?
C7' C6' C5' 121.0(5) . . ?
O5' C6' C5' 114.0(6) . . ?
C6' C7' C8 127.8(5) . . ?
C6' C7' H7'A 116.1 . . ?
C8 C7' H7'A 116.1 . . ?
C11' C10' C9 113.5(6) . . ?
C11' C10' H10B 123.2 . . ?
C9 C10' H10B 123.2 . . ?
C10' C11' C12' 119.7(6) . . ?
C10' C11' C16' 121.1(6) . . ?
C12' C11' C16' 119.2(6) . . ?
C13' C12' C11' 127.0(14) . . ?
C13' C12' H12B 116.4 . . ?
C11' C12' H12B 116.6 . . ?
C12' C13' C14 115(2) . . ?
C12' C13' H13B 122.4 . . ?
C14 C13' H13B 122.2 . . ?
C6' O5' C15' 116.9(5) . . ?
O5' C15' H15D 109.5 . . ?
O5' C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
O5' C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
C11' C16' H16D 109.5 . . ?
C11' C16' H16E 109.5 . . ?
H16D C16' H16E 109.5 . . ?
C11' C16' H16F 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 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
C14 C1 C2 C3 -3.8(2) . . . . ?
C19 C1 C2 C3 175.35(15) . . . . ?
C14 C1 C2 C17 178.25(16) . . . . ?
C19 C1 C2 C17 -2.6(2) . . . . ?
C1 C2 C3 C4 -175.9(5) . . . . ?
C17 C2 C3 C4 2.1(5) . . . . ?
C1 C2 C3 C8 -0.4(2) . . . . ?
C17 C2 C3 C8 177.68(15) . . . . ?
C1 C2 C3 C4' -179.4(6) . . . . ?
C17 C2 C3 C4' -1.4(6) . . . . ?
C4 C3 C8 C7 -0.8(5) . . . . ?
C2 C3 C8 C7 -177.0(3) . . . . ?
C4 C3 C8 C9 -179.8(4) . . . . ?
C2 C3 C8 C9 4.0(2) . . . . ?
C4' C3 C8 C9 -177.1(7) . . . . ?
C2 C3 C8 C7' -175.8(3) . . . . ?
C4' C3 C8 C7' 3.1(8) . . . . ?
C3 C8 C9 C10' 176.0(4) . . . . ?
C7' C8 C9 C10' -4.3(6) . . . . ?
C7 C8 C9 C14 177.4(3) . . . . ?
C3 C8 C9 C14 -3.5(2) . . . . ?
C7' C8 C9 C14 176.2(4) . . . . ?
C7 C8 C9 C10 -4.8(4) . . . . ?
C3 C8 C9 C10 174.3(3) . . . . ?
C8 C9 C14 C13 178.3(11) . . . . ?
C10 C9 C14 C13 0.2(11) . . . . ?
C10' C9 C14 C1 -179.9(5) . . . . ?
C8 C9 C14 C1 -0.6(2) . . . . ?
C10 C9 C14 C1 -178.7(3) . . . . ?
C10' C9 C14 C13' -3.2(15) . . . . ?
C8 C9 C14 C13' 176.1(14) . . . . ?
C2 C1 C14 C13 -174.7(10) . . . . ?
C19 C1 C14 C13 6.2(11) . . . . ?
C2 C1 C14 C9 4.2(2) . . . . ?
C19 C1 C14 C9 -174.91(15) . . . . ?
C2 C1 C14 C13' -171.9(16) . . . . ?
C19 C1 C14 C13' 8.9(16) . . . . ?
C18 O2 C17 O1 3.5(3) . . . . ?
C18 O2 C17 C2 -178.93(18) . . . . ?
C1 C2 C17 O1 -121.6(2) . . . . ?
C3 C2 C17 O1 60.4(3) . . . . ?
C1 C2 C17 O2 60.9(2) . . . . ?
C3 C2 C17 O2 -117.16(18) . . . . ?
C20 O4 C19 O3 0.9(3) . . . . ?
C20 O4 C19 C1 -179.28(18) . . . . ?
C2 C1 C19 O3 -132.0(2) . . . . ?
C14 C1 C19 O3 47.1(3) . . . . ?
C2 C1 C19 O4 48.2(2) . . . . ?
C14 C1 C19 O4 -132.70(17) . . . . ?
C8 C3 C4 C5 1.5(9) . . . . ?
C2 C3 C4 C5 177.3(5) . . . . ?
C3 C4 C5 C6 -2.8(11) . . . . ?
C4 C5 C6 C7 3.2(7) . . . . ?
C4 C5 C6 C16 -177.9(5) . . . . ?
C5 C6 C7 C8 -2.5(6) . . . . ?
C16 C6 C7 C8 178.6(3) . . . . ?
C3 C8 C7 C6 1.4(5) . . . . ?
C9 C8 C7 C6 -179.6(3) . . . . ?
O5 C11 C10 C9 178.7(4) . . . . ?
C12 C11 C10 C9 0.4(7) . . . . ?
C14 C9 C10 C11 0.9(6) . . . . ?
C8 C9 C10 C11 -177.0(3) . . . . ?
O5 C11 C12 C13 178.8(11) . . . . ?
C10 C11 C12 C13 -2.8(12) . . . . ?
C11 C12 C13 C14 4(2) . . . . ?
C9 C14 C13 C12 -3(2) . . . . ?
C1 C14 C13 C12 176.1(13) . . . . ?
C10 C11 O5 C15 0.8(6) . . . . ?
C12 C11 O5 C15 179.2(4) . . . . ?
C8 C3 C4' C5' -3.5(14) . . . . ?
C2 C3 C4' C5' 175.4(8) . . . . ?
C3 C4' C5' C6' 2.8(15) . . . . ?
C4' C5' C6' C7' -2.5(12) . . . . ?
C4' C5' C6' O5' 178.5(9) . . . . ?
O5' C6' C7' C8 -178.6(5) . . . . ?
C5' C6' C7' C8 2.5(11) . . . . ?
C3 C8 C7' C6' -2.7(8) . . . . ?
C9 C8 C7' C6' 177.6(5) . . . . ?
C14 C9 C10' C11' 0.8(10) . . . . ?
C8 C9 C10' C11' -178.7(5) . . . . ?
C9 C10' C11' C12' -0.3(11) . . . . ?
C9 C10' C11' C16' 179.7(5) . . . . ?
C10' C11' C12' C13' 3(2) . . . . ?
C16' C11' C12' C13' -176.9(18) . . . . ?
C11' C12' C13' C14 -6(3) . . . . ?
C9 C14 C13' C12' 5(3) . . . . ?
C1 C14 C13' C12' -178.5(12) . . . . ?
C7' C6' O5' C15' -2.1(8) . . . . ?
C5' C6' O5' C15' 176.8(5) . . . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 2255496'
loop_
_audit_author_name
_audit_author_address
'Konstantin Lyssenko'
;Chemical Department MSU
Russia
;
_audit_update_record             
;
2023-04-11 deposited with the CCDC.	2023-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 O4'
_chemical_formula_sum            'C19 H16 O4'
_chemical_formula_weight         308.32

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   9.0013(18)
_cell_length_b                   16.186(3)
_cell_length_c                   21.094(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3073.3(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    2291
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      50.24

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7088
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 Quest with Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21024
_diffrn_reflns_av_unetI/netI     0.0703
_diffrn_reflns_av_R_equivalents  0.0969
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.931
_diffrn_reflns_theta_max         26.999
_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             3355
_reflns_number_gt                2331
_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          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+2.9206P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3355
_refine_ls_number_parameters     213
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1741
_refine_ls_wR_factor_gt          0.1560
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4679(3) 0.50000(12) 0.60227(9) 0.0419(5) Uani 1 1 d . . . . .
C1 C 0.5224(3) 0.62700(15) 0.65554(12) 0.0286(6) Uani 1 1 d . . . . .
C11 C 0.4608(3) 0.56972(17) 0.85033(12) 0.0372(7) Uani 1 1 d D . . . .
H11A H 0.446697 0.557100 0.894390 0.045 Uiso 0.812(5) 1 d R U P A 1
O2 O 0.3613(2) 0.61770(11) 0.56784(9) 0.0343(5) Uani 1 1 d . . . . .
C2 C 0.6056(3) 0.69365(16) 0.63778(12) 0.0297(6) Uani 1 1 d . . . . .
O3 O 0.5698(2) 0.78868(12) 0.55227(10) 0.0442(5) Uani 1 1 d . . . . .
C3 C 0.6888(3) 0.74124(16) 0.68351(12) 0.0294(6) Uani 1 1 d . . . . .
O4 O 0.6604(2) 0.66202(12) 0.53138(9) 0.0394(5) Uani 1 1 d . . . . .
C4 C 0.7860(3) 0.80567(17) 0.66523(14) 0.0359(6) Uani 1 1 d . . . . .
H4A H 0.796732 0.818737 0.621565 0.043 Uiso 1 1 calc R U . . .
C5 C 0.8649(3) 0.84955(17) 0.70937(15) 0.0388(7) Uani 1 1 d . . . . .
H5A H 0.930437 0.892167 0.696053 0.047 Uiso 1 1 calc R U . . .
C6 C 0.8496(3) 0.83202(16) 0.77361(15) 0.0389(7) Uani 1 1 d D . . . .
H6A H 0.903225 0.863732 0.804516 0.047 Uiso 0.188(5) 1 d R U P A 2
C7 C 0.7572(3) 0.76870(16) 0.79258(13) 0.0339(6) Uani 1 1 d . . . . .
H7A H 0.748719 0.756703 0.836512 0.041 Uiso 1 1 calc R U . . .
C8 C 0.6747(3) 0.72110(15) 0.74883(13) 0.0288(6) Uani 1 1 d . . . . .
C9 C 0.5776(3) 0.65336(15) 0.76795(12) 0.0286(6) Uani 1 1 d . . . . .
C10 C 0.5530(3) 0.63334(16) 0.83232(12) 0.0327(6) Uani 1 1 d . . . . .
H10A H 0.601696 0.664798 0.864161 0.039 Uiso 1 1 calc R U . . .
C12 C 0.3879(3) 0.52385(18) 0.80363(14) 0.0388(7) Uani 1 1 d . . . . .
H12A H 0.323501 0.480117 0.815755 0.047 Uiso 1 1 calc R U . . .
C13 C 0.4078(3) 0.54097(16) 0.74079(13) 0.0330(6) Uani 1 1 d . . . . .
H13A H 0.356767 0.509312 0.709749 0.040 Uiso 1 1 calc R U . . .
C14 C 0.5041(3) 0.60555(15) 0.72151(12) 0.0278(5) Uani 1 1 d . . . . .
C15 C 0.4495(3) 0.57337(16) 0.60680(12) 0.0305(6) Uani 1 1 d . . . . .
C16 C 0.2998(4) 0.57099(18) 0.51546(14) 0.0459(8) Uani 1 1 d . . . . .
H16A H 0.237670 0.607284 0.489372 0.069 Uiso 1 1 calc R U . . .
H16B H 0.239289 0.525481 0.531978 0.069 Uiso 1 1 calc R U . . .
H16C H 0.380753 0.548600 0.489586 0.069 Uiso 1 1 calc R U . . .
C17 C 0.6088(3) 0.72112(17) 0.56973(13) 0.0342(6) Uani 1 1 d . . . . .
C18 C 0.6637(4) 0.6831(2) 0.46461(13) 0.0509(9) Uani 1 1 d . . . . .
H18A H 0.703080 0.636315 0.440344 0.076 Uiso 1 1 calc R U . . .
H18B H 0.727543 0.731431 0.458228 0.076 Uiso 1 1 calc R U . . .
H18C H 0.562839 0.695736 0.450114 0.076 Uiso 1 1 calc R U . . .
C19' C 0.4367(5) 0.5478(2) 0.91921(15) 0.0438(9) Uani 0.812(5) 1 d D . P A 1
H19A H 0.494541 0.585329 0.946044 0.066 Uiso 0.812(5) 1 calc R U P A 1
H19B H 0.468815 0.490802 0.926703 0.066 Uiso 0.812(5) 1 calc R U P A 1
H19C H 0.330949 0.553119 0.929562 0.066 Uiso 0.812(5) 1 calc R U P A 1
C19 C 0.9117(18) 0.8830(8) 0.8274(5) 0.0438(9) Uani 0.188(5) 1 d D . P A 2
H19D H 0.884411 0.857507 0.867943 0.066 Uiso 0.188(5) 1 calc R U P A 2
H19E H 0.870735 0.939008 0.825391 0.066 Uiso 0.188(5) 1 calc R U P A 2
H19F H 1.020129 0.885443 0.823872 0.066 Uiso 0.188(5) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.203(3) . ?
C1 C2 1.366(4) . ?
C1 C14 1.444(3) . ?
C1 C15 1.497(4) . ?
C11 C10 1.376(4) . ?
C11 C12 1.397(4) . ?
C11 C19' 1.511(4) . ?
C11 H11A 0.9600 . ?
O2 C15 1.349(3) . ?
O2 C16 1.449(3) . ?
C2 C3 1.444(4) . ?
C2 C17 1.503(4) . ?
O3 C17 1.206(3) . ?
C3 C4 1.415(4) . ?
C3 C8 1.421(4) . ?
O4 C17 1.336(3) . ?
O4 C18 1.449(3) . ?
C4 C5 1.369(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.391(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.379(4) . ?
C6 C19 1.510(4) . ?
C6 H6A 0.9600 . ?
C7 C8 1.413(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.460(4) . ?
C9 C14 1.413(4) . ?
C9 C10 1.413(4) . ?
C10 H10A 0.9500 . ?
C12 C13 1.366(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.417(4) . ?
C13 H13A 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19' H11A 0.5522 . ?
C19' H19A 0.9800 . ?
C19' H19B 0.9800 . ?
C19' H19C 0.9800 . ?
C19 H6A 0.5799 . ?
C19 H19D 0.9800 . ?
C19 H19E 0.9800 . ?
C19 H19F 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
C2 C1 C14 121.1(2) . . ?
C2 C1 C15 120.7(2) . . ?
C14 C1 C15 118.2(2) . . ?
C10 C11 C12 119.1(2) . . ?
C10 C11 C19' 121.9(3) . . ?
C12 C11 C19' 119.0(3) . . ?
C10 C11 H11A 120.4 . . ?
C12 C11 H11A 120.5 . . ?
C19' C11 H11A 1.5 . . ?
C15 O2 C16 114.3(2) . . ?
C1 C2 C3 121.5(2) . . ?
C1 C2 C17 120.4(2) . . ?
C3 C2 C17 118.1(2) . . ?
C4 C3 C8 119.2(2) . . ?
C4 C3 C2 122.1(2) . . ?
C8 C3 C2 118.6(2) . . ?
C17 O4 C18 115.3(2) . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4A 119.4 . . ?
C3 C4 H4A 119.4 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C7 C6 C5 119.6(3) . . ?
C7 C6 C19 114.2(6) . . ?
C5 C6 C19 125.7(6) . . ?
C7 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
C19 C6 H6A 8.7 . . ?
C6 C7 C8 122.2(3) . . ?
C6 C7 H7A 118.9 . . ?
C8 C7 H7A 118.9 . . ?
C7 C8 C3 117.5(2) . . ?
C7 C8 C9 123.0(2) . . ?
C3 C8 C9 119.6(2) . . ?
C14 C9 C10 117.9(2) . . ?
C14 C9 C8 120.0(2) . . ?
C10 C9 C8 122.1(2) . . ?
C11 C10 C9 122.1(2) . . ?
C11 C10 H10A 119.0 . . ?
C9 C10 H10A 119.0 . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13A 119.7 . . ?
C14 C13 H13A 119.7 . . ?
C9 C14 C13 119.4(2) . . ?
C9 C14 C1 118.9(2) . . ?
C13 C14 C1 121.6(2) . . ?
O1 C15 O2 123.9(2) . . ?
O1 C15 C1 124.5(2) . . ?
O2 C15 C1 111.6(2) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O4 124.4(3) . . ?
O3 C17 C2 123.7(3) . . ?
O4 C17 C2 111.9(2) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C19' H11A 2.5 . . ?
C11 C19' H19A 109.5 . . ?
H11A C19' H19A 107.0 . . ?
C11 C19' H19B 109.5 . . ?
H11A C19' H19B 111.1 . . ?
H19A C19' H19B 109.5 . . ?
C11 C19' H19C 109.5 . . ?
H11A C19' H19C 110.3 . . ?
H19A C19' H19C 109.5 . . ?
H19B C19' H19C 109.5 . . ?
C6 C19 H6A 14.5 . . ?
C6 C19 H19D 109.5 . . ?
H6A C19 H19D 117.9 . . ?
C6 C19 H19E 109.5 . . ?
H6A C19 H19E 114.3 . . ?
H19D C19 H19E 109.5 . . ?
C6 C19 H19F 109.5 . . ?
H6A C19 H19F 95.1 . . ?
H19D C19 H19F 109.5 . . ?
H19E C19 H19F 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
C14 C1 C2 C3 5.3(4) . . . . ?
C15 C1 C2 C3 -173.7(2) . . . . ?
C14 C1 C2 C17 -172.7(2) . . . . ?
C15 C1 C2 C17 8.3(4) . . . . ?
C1 C2 C3 C4 174.2(2) . . . . ?
C17 C2 C3 C4 -7.8(4) . . . . ?
C1 C2 C3 C8 -4.4(4) . . . . ?
C17 C2 C3 C8 173.7(2) . . . . ?
C8 C3 C4 C5 -0.9(4) . . . . ?
C2 C3 C4 C5 -179.4(3) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 C7 1.6(4) . . . . ?
C4 C5 C6 C19 -170.5(8) . . . . ?
C5 C6 C7 C8 -1.0(4) . . . . ?
C19 C6 C7 C8 172.1(7) . . . . ?
C6 C7 C8 C3 -0.6(4) . . . . ?
C6 C7 C8 C9 179.4(2) . . . . ?
C4 C3 C8 C7 1.5(4) . . . . ?
C2 C3 C8 C7 -179.9(2) . . . . ?
C4 C3 C8 C9 -178.5(2) . . . . ?
C2 C3 C8 C9 0.1(4) . . . . ?
C7 C8 C9 C14 -176.8(2) . . . . ?
C3 C8 C9 C14 3.2(4) . . . . ?
C7 C8 C9 C10 3.4(4) . . . . ?
C3 C8 C9 C10 -176.6(2) . . . . ?
C12 C11 C10 C9 -0.6(4) . . . . ?
C19' C11 C10 C9 179.1(3) . . . . ?
C14 C9 C10 C11 -0.1(4) . . . . ?
C8 C9 C10 C11 179.7(2) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C19' C11 C12 C13 -179.3(3) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C10 C9 C14 C13 1.0(4) . . . . ?
C8 C9 C14 C13 -178.8(2) . . . . ?
C10 C9 C14 C1 177.4(2) . . . . ?
C8 C9 C14 C1 -2.4(4) . . . . ?
C12 C13 C14 C9 -1.2(4) . . . . ?
C12 C13 C14 C1 -177.5(3) . . . . ?
C2 C1 C14 C9 -1.8(4) . . . . ?
C15 C1 C14 C9 177.2(2) . . . . ?
C2 C1 C14 C13 174.5(2) . . . . ?
C15 C1 C14 C13 -6.5(4) . . . . ?
C16 O2 C15 O1 -5.5(4) . . . . ?
C16 O2 C15 C1 173.8(2) . . . . ?
C2 C1 C15 O1 123.7(3) . . . . ?
C14 C1 C15 O1 -55.3(4) . . . . ?
C2 C1 C15 O2 -55.6(3) . . . . ?
C14 C1 C15 O2 125.3(2) . . . . ?
C18 O4 C17 O3 -1.7(4) . . . . ?
C18 O4 C17 C2 178.6(2) . . . . ?
C1 C2 C17 O3 120.1(3) . . . . ?
C3 C2 C17 O3 -57.9(4) . . . . ?
C1 C2 C17 O4 -60.3(3) . . . . ?
C3 C2 C17 O4 121.7(3) . . . . ?

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_b_a
_database_code_depnum_ccdc_archive 'CCDC 2257444'
loop_
_audit_author_name
_audit_author_address
'Konstantin Lyssenko'
;Chemical Department MSU
Russia
;
_audit_update_record             
;
2023-04-19 deposited with the CCDC.	2023-08-18 downloaded from the CCDC.
;
_audit_creation_date             2023-04-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 N O5'
_chemical_formula_sum            'C22 H19 N O5'
_chemical_formula_weight         377.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   10.4074(6)
_cell_length_b                   18.1894(10)
_cell_length_c                   9.8502(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.929(2)
_cell_angle_gamma                90
_cell_volume                     1830.87(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4288
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.7843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1718 before and 0.0668 after correction.
The Ratio of minimum to maximum transmission is 0.9096.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0764
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26142
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_min         1.993
_diffrn_ambient_temperature      101.00
_diffrn_detector                 'Photon III detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4029
_reflns_number_total             4868
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4868
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0548
_refine_ls_restrained_S_all      1.052
_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)+(0.0681P)²+0.7556P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1431
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.33509(10) 0.41909(6) 0.78853(11) 0.0198(2) Uani 1 1 d . . . . .
O1 O 0.31722(11) 0.25095(6) 0.72839(11) 0.0210(2) Uani 1 1 d . . . . .
O2 O 0.22017(10) 0.40333(6) 0.57288(12) 0.0220(2) Uani 1 1 d . . . . .
O5 O 0.47280(11) 0.53692(6) 0.70338(12) 0.0236(2) Uani 1 1 d . . . . .
O4 O 0.63039(12) 0.48761(7) 0.86418(13) 0.0319(3) Uani 1 1 d . . . . .
N1 N 0.34342(12) 0.26625(7) 0.50864(13) 0.0161(2) Uani 1 1 d . . . . .
C11 C 0.27787(14) 0.24031(8) 0.60376(15) 0.0158(3) Uani 1 1 d . . . . .
C12 C 0.15687(14) 0.19685(8) 0.55320(15) 0.0172(3) Uani 1 1 d . . . . .
C3 C 0.55725(14) 0.42075(8) 0.65719(15) 0.0173(3) Uani 1 1 d . . . . .
C2 C 0.44862(14) 0.37678(8) 0.62018(14) 0.0162(3) Uani 1 1 d . . . . .
C9 C 0.68156(14) 0.33890(8) 0.53325(15) 0.0182(3) Uani 1 1 d . . . . .
C13 C 0.07779(15) 0.20858(9) 0.42458(16) 0.0203(3) Uani 1 1 d . . . . .
C10 C 0.57187(14) 0.29029(8) 0.50520(15) 0.0171(3) Uani 1 1 d . . . . .
C4 C 0.67524(14) 0.40437(8) 0.60977(15) 0.0183(3) Uani 1 1 d . . . . .
C1 C 0.45671(14) 0.31122(8) 0.54363(14) 0.0160(3) Uani 1 1 d . . . . .
C20 C 0.55810(14) 0.48452(8) 0.75342(17) 0.0208(3) Uani 1 1 d . . . . .
C5 C 0.78320(15) 0.45293(9) 0.63210(17) 0.0218(3) Uani 1 1 d . . . . .
C18 C 0.32127(14) 0.40013(8) 0.65503(15) 0.0172(3) Uani 1 1 d . . . . .
C6 C 0.89367(15) 0.43717(9) 0.58158(17) 0.0244(3) Uani 1 1 d . . . . .
C22 C 0.58468(15) 0.21849(9) 0.43393(17) 0.0213(3) Uani 1 1 d . . . . .
C19 C 0.22265(15) 0.45556(10) 0.82418(18) 0.0244(3) Uani 1 1 d . . . . .
C14 C -0.03624(15) 0.16760(9) 0.38554(18) 0.0244(3) Uani 1 1 d . . . . .
C8 C 0.79859(15) 0.32389(9) 0.48482(17) 0.0237(3) Uani 1 1 d . . . . .
C17 C 0.12212(16) 0.14408(9) 0.64188(17) 0.0240(3) Uani 1 1 d . . . . .
C7 C 0.90210(16) 0.37197(10) 0.50825(18) 0.0257(3) Uani 1 1 d . . . . .
C15 C -0.06959(16) 0.11433(10) 0.4735(2) 0.0287(4) Uani 1 1 d . . . . .
C16 C 0.00930(17) 0.10240(10) 0.6007(2) 0.0302(4) Uani 1 1 d . . . . .
C21 C 0.4621(2) 0.59543(9) 0.7999(2) 0.0312(4) Uani 1 1 d . . . . .
H1 H 0.3171(19) 0.2567(10) 0.422(2) 0.022(5) Uiso 1 1 d . . . . .
H19A H 0.145(2) 0.4230(11) 0.800(2) 0.027(5) Uiso 1 1 d . . . . .
H22A H 0.509(2) 0.1869(11) 0.432(2) 0.031(5) Uiso 1 1 d . . . . .
H14 H -0.090(2) 0.1750(12) 0.300(2) 0.034(6) Uiso 1 1 d . . . . .
H5 H 0.7801(19) 0.4977(12) 0.682(2) 0.028(5) Uiso 1 1 d . . . . .
H7 H 0.981(2) 0.3599(12) 0.474(2) 0.032(5) Uiso 1 1 d . . . . .
H13 H 0.1032(18) 0.2445(11) 0.363(2) 0.021(5) Uiso 1 1 d . . . . .
H6 H 0.9660(19) 0.4705(11) 0.597(2) 0.024(5) Uiso 1 1 d . . . . .
H19B H 0.247(2) 0.4642(12) 0.921(2) 0.034(6) Uiso 1 1 d . . . . .
H17 H 0.1787(19) 0.1381(11) 0.732(2) 0.027(5) Uiso 1 1 d . . . . .
H21A H 0.540(2) 0.6231(14) 0.813(2) 0.045(6) Uiso 1 1 d . . . . .
H22B H 0.599(2) 0.2243(12) 0.336(2) 0.032(5) Uiso 1 1 d . . . . .
H19C H 0.205(2) 0.5026(13) 0.768(2) 0.038(6) Uiso 1 1 d . . . . .
H22C H 0.6606(19) 0.1904(11) 0.483(2) 0.024(5) Uiso 1 1 d . . . . .
H21B H 0.387(3) 0.6256(14) 0.754(3) 0.051(7) Uiso 1 1 d . . . . .
H16 H -0.014(2) 0.0642(14) 0.659(3) 0.043(6) Uiso 1 1 d . . . . .
H21C H 0.447(2) 0.5751(13) 0.892(3) 0.044(6) Uiso 1 1 d . . . . .
H15 H -0.145(2) 0.0843(12) 0.446(2) 0.037(6) Uiso 1 1 d . . . . .
H8 H 0.8051(19) 0.2793(12) 0.434(2) 0.027(5) 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
O3 C18 1.3406(18) . ?
O3 C19 1.4451(18) . ?
O1 C11 1.2336(18) . ?
O2 C18 1.2009(18) . ?
O5 C20 1.3319(19) . ?
O5 C21 1.445(2) . ?
O4 C20 1.2034(19) . ?
N1 C11 1.3447(18) . ?
N1 C1 1.4227(18) . ?
N1 H1 0.86(2) . ?
C11 C12 1.4903(19) . ?
C12 C13 1.390(2) . ?
C12 C17 1.391(2) . ?
C3 C2 1.3764(19) . ?
C3 C4 1.426(2) . ?
C3 C20 1.497(2) . ?
C2 C1 1.422(2) . ?
C2 C18 1.492(2) . ?
C9 C10 1.429(2) . ?
C9 C4 1.418(2) . ?
C9 C8 1.416(2) . ?
C13 C14 1.392(2) . ?
C13 H13 0.96(2) . ?
C10 C1 1.3772(19) . ?
C10 C22 1.501(2) . ?
C4 C5 1.413(2) . ?
C5 C6 1.367(2) . ?
C5 H5 0.96(2) . ?
C6 C7 1.400(2) . ?
C6 H6 0.96(2) . ?
C22 H22A 0.97(2) . ?
C22 H22B 1.01(2) . ?
C22 H22C 0.99(2) . ?
C19 H19A 1.00(2) . ?
C19 H19B 0.95(2) . ?
C19 H19C 1.01(2) . ?
C14 C15 1.387(3) . ?
C14 H14 0.93(2) . ?
C8 C7 1.373(2) . ?
C8 H8 0.96(2) . ?
C17 C16 1.392(2) . ?
C17 H17 0.98(2) . ?
C7 H7 0.97(2) . ?
C15 C16 1.379(3) . ?
C15 H15 0.95(2) . ?
C16 H16 0.97(3) . ?
C21 H21A 0.95(3) . ?
C21 H21B 0.99(3) . ?
C21 H21C 1.02(2) . ?

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
C18 O3 C19 114.53(12) . . ?
C20 O5 C21 114.37(13) . . ?
C11 N1 C1 122.65(12) . . ?
C11 N1 H1 120.6(13) . . ?
C1 N1 H1 116.7(13) . . ?
O1 C11 N1 121.46(13) . . ?
O1 C11 C12 121.05(13) . . ?
N1 C11 C12 117.48(13) . . ?
C13 C12 C11 122.68(13) . . ?
C13 C12 C17 119.91(14) . . ?
C17 C12 C11 117.39(13) . . ?
C2 C3 C4 120.47(13) . . ?
C2 C3 C20 121.59(13) . . ?
C4 C3 C20 117.87(13) . . ?
C3 C2 C1 119.97(13) . . ?
C3 C2 C18 119.63(13) . . ?
C1 C2 C18 120.34(12) . . ?
C4 C9 C10 120.45(13) . . ?
C8 C9 C10 121.48(14) . . ?
C8 C9 C4 118.07(14) . . ?
C12 C13 C14 119.73(15) . . ?
C12 C13 H13 119.5(11) . . ?
C14 C13 H13 120.7(11) . . ?
C9 C10 C22 119.37(13) . . ?
C1 C10 C9 118.74(13) . . ?
C1 C10 C22 121.89(13) . . ?
C9 C4 C3 118.65(13) . . ?
C5 C4 C3 121.82(14) . . ?
C5 C4 C9 119.48(14) . . ?
C2 C1 N1 118.75(12) . . ?
C10 C1 N1 119.93(13) . . ?
C10 C1 C2 121.31(13) . . ?
O5 C20 C3 113.37(13) . . ?
O4 C20 O5 124.08(14) . . ?
O4 C20 C3 122.55(14) . . ?
C4 C5 H5 120.7(12) . . ?
C6 C5 C4 120.74(15) . . ?
C6 C5 H5 118.6(12) . . ?
O3 C18 C2 111.35(12) . . ?
O2 C18 O3 124.46(14) . . ?
O2 C18 C2 124.17(14) . . ?
C5 C6 C7 120.32(15) . . ?
C5 C6 H6 120.0(12) . . ?
C7 C6 H6 119.7(12) . . ?
C10 C22 H22A 112.3(12) . . ?
C10 C22 H22B 113.5(12) . . ?
C10 C22 H22C 110.7(11) . . ?
H22A C22 H22B 108.2(17) . . ?
H22A C22 H22C 105.8(16) . . ?
H22B C22 H22C 106.0(17) . . ?
O3 C19 H19A 109.3(12) . . ?
O3 C19 H19B 104.2(13) . . ?
O3 C19 H19C 109.4(13) . . ?
H19A C19 H19B 112.9(18) . . ?
H19A C19 H19C 108.2(17) . . ?
H19B C19 H19C 112.8(18) . . ?
C13 C14 H14 120.9(13) . . ?
C15 C14 C13 120.17(16) . . ?
C15 C14 H14 119.0(13) . . ?
C9 C8 H8 119.2(12) . . ?
C7 C8 C9 121.21(15) . . ?
C7 C8 H8 119.6(12) . . ?
C12 C17 C16 119.87(16) . . ?
C12 C17 H17 117.8(12) . . ?
C16 C17 H17 122.3(12) . . ?
C6 C7 H7 120.9(13) . . ?
C8 C7 C6 120.16(15) . . ?
C8 C7 H7 118.9(13) . . ?
C14 C15 H15 120.8(14) . . ?
C16 C15 C14 120.07(15) . . ?
C16 C15 H15 119.1(14) . . ?
C17 C16 H16 120.8(14) . . ?
C15 C16 C17 120.23(16) . . ?
C15 C16 H16 118.9(14) . . ?
O5 C21 H21A 108.1(15) . . ?
O5 C21 H21B 105.2(15) . . ?
O5 C21 H21C 111.2(14) . . ?
H21A C21 H21B 111(2) . . ?
H21A C21 H21C 110(2) . . ?
H21B C21 H21C 111(2) . . ?

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 C11 C12 C13 151.20(15) . . . . ?
O1 C11 C12 C17 -27.1(2) . . . . ?
N1 C11 C12 C13 -29.9(2) . . . . ?
N1 C11 C12 C17 151.77(14) . . . . ?
C11 N1 C1 C2 -54.99(19) . . . . ?
C11 N1 C1 C10 124.01(15) . . . . ?
C11 C12 C13 C14 -177.94(14) . . . . ?
C11 C12 C17 C16 179.32(15) . . . . ?
C12 C13 C14 C15 -1.2(2) . . . . ?
C12 C17 C16 C15 -1.4(3) . . . . ?
C3 C2 C1 N1 179.04(13) . . . . ?
C3 C2 C1 C10 0.1(2) . . . . ?
C3 C2 C18 O3 -50.10(18) . . . . ?
C3 C2 C18 O2 128.05(16) . . . . ?
C3 C4 C5 C6 -177.77(15) . . . . ?
C2 C3 C4 C9 -5.0(2) . . . . ?
C2 C3 C4 C5 172.39(14) . . . . ?
C2 C3 C20 O5 -63.71(19) . . . . ?
C2 C3 C20 O4 117.04(18) . . . . ?
C9 C10 C1 N1 175.73(13) . . . . ?
C9 C10 C1 C2 -5.3(2) . . . . ?
C9 C4 C5 C6 -0.4(2) . . . . ?
C9 C8 C7 C6 0.2(3) . . . . ?
C13 C12 C17 C16 1.0(2) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C10 C9 C4 C3 -0.4(2) . . . . ?
C10 C9 C4 C5 -177.77(14) . . . . ?
C10 C9 C8 C7 177.86(15) . . . . ?
C4 C3 C2 C1 5.2(2) . . . . ?
C4 C3 C2 C18 -171.95(13) . . . . ?
C4 C3 C20 O5 119.37(15) . . . . ?
C4 C3 C20 O4 -59.9(2) . . . . ?
C4 C9 C10 C1 5.4(2) . . . . ?
C4 C9 C10 C22 -175.14(13) . . . . ?
C4 C9 C8 C7 -1.5(2) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C1 N1 C11 O1 -4.1(2) . . . . ?
C1 N1 C11 C12 177.05(12) . . . . ?
C1 C2 C18 O3 132.78(14) . . . . ?
C1 C2 C18 O2 -49.1(2) . . . . ?
C20 C3 C2 C1 -171.66(13) . . . . ?
C20 C3 C2 C18 11.2(2) . . . . ?
C20 C3 C4 C9 171.99(13) . . . . ?
C20 C3 C4 C5 -10.7(2) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C18 C2 C1 N1 -3.8(2) . . . . ?
C18 C2 C1 C10 177.17(13) . . . . ?
C22 C10 C1 N1 -3.7(2) . . . . ?
C22 C10 C1 C2 175.25(13) . . . . ?
C19 O3 C18 O2 -9.5(2) . . . . ?
C19 O3 C18 C2 168.63(12) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C8 C9 C10 C1 -173.92(14) . . . . ?
C8 C9 C10 C22 5.5(2) . . . . ?
C8 C9 C4 C3 178.98(14) . . . . ?
C8 C9 C4 C5 1.6(2) . . . . ?
C17 C12 C13 C14 0.3(2) . . . . ?
C21 O5 C20 O4 -6.8(2) . . . . ?
C21 O5 C20 C3 173.91(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2255495'
loop_
_audit_author_name
_audit_author_address
'Konstantin Lyssenko'
;Chemical Department MSU
Russia
;
_audit_update_record             
;
2023-04-11 deposited with the CCDC.	2023-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 O4'
_chemical_formula_sum            'C19 H18 O4'
_chemical_formula_weight         310.33

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                   10.583(8)
_cell_length_b                   7.649(6)
_cell_length_c                   20.107(14)
_cell_angle_alpha                90
_cell_angle_beta                 104.03(2)
_cell_angle_gamma                90
_cell_volume                     1579(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    542
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      18.22

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6238
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 Quest with Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11685
_diffrn_reflns_av_unetI/netI     0.1840
_diffrn_reflns_av_R_equivalents  0.1686
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.005
_diffrn_reflns_theta_max         25.997
_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             3098
_reflns_number_gt                1559
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0785P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3098
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1618
_refine_ls_R_factor_gt           0.0893
_refine_ls_wR_factor_ref         0.2582
_refine_ls_wR_factor_gt          0.2088
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6525(3) 0.1411(4) 0.44814(15) 0.0342(8) Uani 1 1 d . . . . .
C1 C 0.6772(4) 0.4520(6) 0.4415(2) 0.0296(11) Uani 1 1 d . . . . .
O2 O 0.6156(3) 0.3103(4) 0.53218(15) 0.0345(8) Uani 1 1 d . . . . .
C2 C 0.6180(4) 0.4858(6) 0.3756(2) 0.0307(11) Uani 1 1 d . . . . .
O3 O 0.7727(3) 0.6415(4) 0.32646(17) 0.0395(9) Uani 1 1 d . . . . .
C3 C 0.7769(4) 0.5614(6) 0.4875(2) 0.0292(11) Uani 1 1 d . . . . .
O4 O 0.5714(3) 0.7499(4) 0.31693(16) 0.0346(8) Uani 1 1 d . . . . .
C4 C 0.8746(4) 0.4851(6) 0.5384(2) 0.0330(11) Uani 1 1 d . . . . .
H4A H 0.876770 0.361618 0.543614 0.040 Uiso 1 1 calc R U . . .
C5 C 0.9679(4) 0.5851(6) 0.5813(2) 0.0338(11) Uani 1 1 d . . . . .
H5A H 1.032946 0.529462 0.615639 0.041 Uiso 1 1 calc R U . . .
C6 C 0.9689(4) 0.7656(7) 0.5753(2) 0.0333(11) Uani 1 1 d . . . . .
C7 C 0.8706(4) 0.8425(6) 0.5254(2) 0.0302(10) Uani 1 1 d . . . . .
H7A H 0.868991 0.966104 0.520575 0.036 Uiso 1 1 calc R U . . .
C8 C 0.7760(4) 0.7449(6) 0.4830(2) 0.0293(11) Uani 1 1 d . . . . .
H8A H 0.708912 0.801713 0.450092 0.035 Uiso 1 1 calc R U . . .
C9 C 1.0716(5) 0.8745(7) 0.6219(2) 0.0407(13) Uani 1 1 d . . . . .
H9A H 1.132480 0.797915 0.653321 0.061 Uiso 1 1 calc R U . . .
H9B H 1.030222 0.954374 0.648376 0.061 Uiso 1 1 calc R U . . .
H9C H 1.118973 0.942359 0.594431 0.061 Uiso 1 1 calc R U . . .
C10 C 0.5050(4) 0.3879(5) 0.3341(2) 0.0277(10) Uani 1 1 d . . . . .
C11 C 0.4983(5) 0.3450(6) 0.2657(2) 0.0324(11) Uani 1 1 d . . . . .
H11A H 0.568128 0.375511 0.245910 0.039 Uiso 1 1 calc R U . . .
C12 C 0.3913(5) 0.2587(6) 0.2269(3) 0.0369(12) Uani 1 1 d . . . . .
H12A H 0.388355 0.229088 0.180629 0.044 Uiso 1 1 calc R U . . .
C13 C 0.2885(5) 0.2152(6) 0.2547(3) 0.0362(12) Uani 1 1 d . . . . .
H13A H 0.214623 0.156845 0.227521 0.043 Uiso 1 1 calc R U . . .
C14 C 0.2931(5) 0.2566(6) 0.3222(3) 0.0363(12) Uani 1 1 d . . . . .
H14A H 0.222967 0.225081 0.341657 0.044 Uiso 1 1 calc R U . . .
C15 C 0.4002(4) 0.3444(6) 0.3614(2) 0.0318(11) Uani 1 1 d . . . . .
H15A H 0.402133 0.375105 0.407460 0.038 Uiso 1 1 calc R U . . .
C16 C 0.6456(4) 0.2819(6) 0.4727(2) 0.0292(11) Uani 1 1 d . . . . .
C17 C 0.5997(5) 0.1546(6) 0.5714(2) 0.0392(12) Uani 1 1 d . . . . .
H17A H 0.577448 0.189685 0.614075 0.059 Uiso 1 1 calc R U . . .
H17B H 0.681173 0.087988 0.582224 0.059 Uiso 1 1 calc R U . . .
H17C H 0.529690 0.081809 0.544293 0.059 Uiso 1 1 calc R U . . .
C18 C 0.6662(4) 0.6325(6) 0.3379(2) 0.0305(11) Uani 1 1 d . . . . .
C19 C 0.6051(5) 0.9040(6) 0.2827(3) 0.0423(13) Uani 1 1 d . . . . .
H19A H 0.528771 0.980428 0.269341 0.063 Uiso 1 1 calc R U . . .
H19B H 0.633145 0.868501 0.241656 0.063 Uiso 1 1 calc R U . . .
H19C H 0.675944 0.967061 0.313837 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 C16 1.195(5) . ?
C1 C2 1.346(6) . ?
C1 C3 1.482(6) . ?
C1 C16 1.517(6) . ?
O2 C16 1.327(5) . ?
O2 C17 1.460(6) . ?
C2 C10 1.484(6) . ?
C2 C18 1.511(6) . ?
O3 C18 1.206(5) . ?
C3 C4 1.395(6) . ?
C3 C8 1.406(6) . ?
O4 C18 1.335(5) . ?
O4 C19 1.453(5) . ?
C4 C5 1.374(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.386(7) . ?
C5 H5A 0.9500 . ?
C6 C7 1.389(6) . ?
C6 C9 1.503(6) . ?
C7 C8 1.369(6) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.392(6) . ?
C10 C11 1.399(6) . ?
C11 C12 1.378(6) . ?
C11 H11A 0.9500 . ?
C12 C13 1.380(7) . ?
C12 H12A 0.9500 . ?
C13 C14 1.383(7) . ?
C13 H13A 0.9500 . ?
C14 C15 1.388(6) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C2 C1 C3 126.7(4) . . ?
C2 C1 C16 118.4(4) . . ?
C3 C1 C16 114.9(4) . . ?
C16 O2 C17 115.9(4) . . ?
C1 C2 C10 125.1(4) . . ?
C1 C2 C18 120.2(4) . . ?
C10 C2 C18 114.6(4) . . ?
C4 C3 C8 117.2(4) . . ?
C4 C3 C1 120.7(4) . . ?
C8 C3 C1 122.0(4) . . ?
C18 O4 C19 116.3(4) . . ?
C5 C4 C3 121.3(5) . . ?
C5 C4 H4A 119.4 . . ?
C3 C4 H4A 119.4 . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C5 C6 C7 117.7(4) . . ?
C5 C6 C9 121.2(4) . . ?
C7 C6 C9 121.2(5) . . ?
C8 C7 C6 121.7(4) . . ?
C8 C7 H7A 119.1 . . ?
C6 C7 H7A 119.1 . . ?
C7 C8 C3 120.8(4) . . ?
C7 C8 H8A 119.6 . . ?
C3 C8 H8A 119.6 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.4(4) . . ?
C15 C10 C2 120.6(4) . . ?
C11 C10 C2 120.9(4) . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C11 C12 C13 120.4(5) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C12 C13 C14 120.0(5) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C13 C14 C15 119.9(5) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C14 C15 C10 120.7(4) . . ?
C14 C15 H15A 119.6 . . ?
C10 C15 H15A 119.6 . . ?
O1 C16 O2 124.9(4) . . ?
O1 C16 C1 124.0(4) . . ?
O2 C16 C1 111.0(4) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 O4 124.5(4) . . ?
O3 C18 C2 125.6(4) . . ?
O4 C18 C2 109.8(4) . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C3 C1 C2 C10 -170.4(4) . . . . ?
C16 C1 C2 C10 12.5(7) . . . . ?
C3 C1 C2 C18 10.0(7) . . . . ?
C16 C1 C2 C18 -167.1(4) . . . . ?
C2 C1 C3 C4 -147.8(5) . . . . ?
C16 C1 C3 C4 29.4(6) . . . . ?
C2 C1 C3 C8 33.6(7) . . . . ?
C16 C1 C3 C8 -149.2(4) . . . . ?
C8 C3 C4 C5 -1.6(6) . . . . ?
C1 C3 C4 C5 179.8(4) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
C4 C5 C6 C7 1.3(6) . . . . ?
C4 C5 C6 C9 -179.6(4) . . . . ?
C5 C6 C7 C8 -0.4(6) . . . . ?
C9 C6 C7 C8 -179.5(4) . . . . ?
C6 C7 C8 C3 -1.5(7) . . . . ?
C4 C3 C8 C7 2.5(6) . . . . ?
C1 C3 C8 C7 -178.9(4) . . . . ?
C1 C2 C10 C15 44.5(7) . . . . ?
C18 C2 C10 C15 -135.9(4) . . . . ?
C1 C2 C10 C11 -138.7(5) . . . . ?
C18 C2 C10 C11 40.9(6) . . . . ?
C15 C10 C11 C12 -1.2(7) . . . . ?
C2 C10 C11 C12 -178.0(4) . . . . ?
C10 C11 C12 C13 0.7(7) . . . . ?
C11 C12 C13 C14 -0.6(7) . . . . ?
C12 C13 C14 C15 1.0(7) . . . . ?
C13 C14 C15 C10 -1.5(7) . . . . ?
C11 C10 C15 C14 1.5(7) . . . . ?
C2 C10 C15 C14 178.4(4) . . . . ?
C17 O2 C16 O1 4.7(7) . . . . ?
C17 O2 C16 C1 -172.4(4) . . . . ?
C2 C1 C16 O1 52.9(6) . . . . ?
C3 C1 C16 O1 -124.6(5) . . . . ?
C2 C1 C16 O2 -130.0(4) . . . . ?
C3 C1 C16 O2 52.5(5) . . . . ?
C19 O4 C18 O3 -4.8(7) . . . . ?
C19 O4 C18 C2 177.0(4) . . . . ?
C1 C2 C18 O3 62.1(7) . . . . ?
C10 C2 C18 O3 -117.6(5) . . . . ?
C1 C2 C18 O4 -119.8(5) . . . . ?
C10 C2 C18 O4 60.6(5) . . . . ?

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_a_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2255494'
loop_
_audit_author_name
_audit_author_address
'Konstantin Lyssenko'
;Chemical Department MSU
Russia
;
_audit_update_record             
;
2023-04-11 deposited with the CCDC.	2023-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 O5'
_chemical_formula_sum            'C19 H18 O5'
_chemical_formula_weight         326.33

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                   9.538(2)
_cell_length_b                   10.289(2)
_cell_length_c                   16.613(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.677(10)
_cell_angle_gamma                90
_cell_volume                     1625.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    139(2)
_cell_measurement_reflns_used    1661
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      28.12

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.992

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8238
_exptl_absorpt_correction_T_max  0.9622
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      139(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 Quest with Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12180
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.330
_diffrn_reflns_theta_max         27.500
_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             3739
_reflns_number_gt                2695
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0352P)²+0.8335P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3739
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1416
_refine_ls_wR_factor_gt          0.1283
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.99988(16) 0.73189(16) 0.70052(10) 0.0285(4) Uani 1 1 d . . . . .
O2 O 0.34641(17) 0.66336(18) 0.65676(10) 0.0329(4) Uani 1 1 d . . . . .
O3 O 0.27623(16) 0.55464(15) 0.54372(9) 0.0257(4) Uani 1 1 d . . . . .
O4 O 0.62731(17) 0.73695(17) 0.39185(10) 0.0342(4) Uani 1 1 d . . . . .
O5 O 0.51701(16) 0.92833(15) 0.39386(10) 0.0293(4) Uani 1 1 d . . . . .
C1 C 0.4601(2) 0.7037(2) 0.53697(13) 0.0221(5) Uani 1 1 d . . . . .
C2 C 0.4214(2) 0.7566(2) 0.46445(13) 0.0217(5) Uani 1 1 d . . . . .
C3 C 0.6048(2) 0.7120(2) 0.57656(12) 0.0204(4) Uani 1 1 d . . . . .
C4 C 0.6706(2) 0.6029(2) 0.61334(13) 0.0233(5) Uani 1 1 d . . . . .
H4A H 0.623172 0.521618 0.611352 0.028 Uiso 1 1 calc R U . . .
C5 C 0.8031(2) 0.6122(2) 0.65227(13) 0.0238(5) Uani 1 1 d . . . . .
H5A H 0.847947 0.537010 0.675465 0.029 Uiso 1 1 calc R U . . .
C6 C 0.8718(2) 0.7322(2) 0.65770(13) 0.0214(5) Uani 1 1 d . . . . .
C7 C 0.8078(2) 0.8414(2) 0.62251(13) 0.0229(5) Uani 1 1 d . . . . .
H7A H 0.853777 0.923310 0.626180 0.028 Uiso 1 1 calc R U . . .
C8 C 0.6759(2) 0.8294(2) 0.58198(13) 0.0237(5) Uani 1 1 d . . . . .
H8A H 0.632791 0.904022 0.557066 0.028 Uiso 1 1 calc R U . . .
C9 C 1.0729(2) 0.8530(2) 0.70937(15) 0.0315(6) Uani 1 1 d . . . . .
H9A H 1.163020 0.839850 0.741089 0.047 Uiso 1 1 calc R U . . .
H9B H 1.015880 0.915257 0.737165 0.047 Uiso 1 1 calc R U . . .
H9C H 1.090003 0.887005 0.655934 0.047 Uiso 1 1 calc R U . . .
C10 C 0.2749(2) 0.7730(2) 0.42821(13) 0.0214(4) Uani 1 1 d . . . . .
C11 C 0.1652(2) 0.8105(2) 0.47392(14) 0.0262(5) Uani 1 1 d . . . . .
H11A H 0.184009 0.828026 0.529904 0.031 Uiso 1 1 calc R U . . .
C12 C 0.0298(2) 0.8223(2) 0.43876(15) 0.0296(5) Uani 1 1 d . . . . .
H12A H -0.043836 0.846825 0.470854 0.036 Uiso 1 1 calc R U . . .
C13 C 0.0004(2) 0.7989(2) 0.35724(15) 0.0287(5) Uani 1 1 d . . . . .
H13A H -0.093205 0.806370 0.333301 0.034 Uiso 1 1 calc R U . . .
C14 C 0.1082(2) 0.7646(2) 0.31100(14) 0.0281(5) Uani 1 1 d . . . . .
H14A H 0.088999 0.749689 0.254747 0.034 Uiso 1 1 calc R U . . .
C15 C 0.2444(2) 0.7518(2) 0.34605(13) 0.0246(5) Uani 1 1 d . . . . .
H15A H 0.317755 0.728229 0.313508 0.029 Uiso 1 1 calc R U . . .
C16 C 0.3551(2) 0.6404(2) 0.58656(13) 0.0227(5) Uani 1 1 d . . . . .
C17 C 0.1643(2) 0.4948(2) 0.58352(16) 0.0315(5) Uani 1 1 d . . . . .
H17A H 0.113523 0.433667 0.546489 0.047 Uiso 1 1 calc R U . . .
H17B H 0.099307 0.562012 0.599623 0.047 Uiso 1 1 calc R U . . .
H17C H 0.203768 0.448121 0.631538 0.047 Uiso 1 1 calc R U . . .
C18 C 0.5350(2) 0.8036(2) 0.41369(13) 0.0212(5) Uani 1 1 d . . . . .
C19 C 0.6203(2) 0.9818(2) 0.34444(15) 0.0321(6) Uani 1 1 d . . . . .
H19A H 0.598721 1.073442 0.333182 0.048 Uiso 1 1 calc R U . . .
H19B H 0.618356 0.933587 0.293478 0.048 Uiso 1 1 calc R U . . .
H19C H 0.713946 0.974660 0.373056 0.048 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 C6 1.362(3) . ?
O1 C9 1.430(3) . ?
O2 C16 1.199(3) . ?
O3 C16 1.328(3) . ?
O3 C17 1.439(3) . ?
O4 C18 1.196(3) . ?
O5 C18 1.333(3) . ?
O5 C19 1.442(3) . ?
C1 C2 1.346(3) . ?
C1 C3 1.482(3) . ?
C1 C16 1.497(3) . ?
C2 C10 1.485(3) . ?
C2 C18 1.506(3) . ?
C3 C8 1.385(3) . ?
C3 C4 1.402(3) . ?
C4 C5 1.375(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.397(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.386(3) . ?
C7 C8 1.383(3) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.389(3) . ?
C10 C11 1.397(3) . ?
C11 C12 1.378(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.382(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.379(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C6 O1 C9 117.43(18) . . ?
C16 O3 C17 116.55(18) . . ?
C18 O5 C19 115.35(17) . . ?
C2 C1 C3 123.5(2) . . ?
C2 C1 C16 121.4(2) . . ?
C3 C1 C16 114.93(18) . . ?
C1 C2 C10 126.1(2) . . ?
C1 C2 C18 118.25(19) . . ?
C10 C2 C18 115.64(18) . . ?
C8 C3 C4 118.1(2) . . ?
C8 C3 C1 120.80(19) . . ?
C4 C3 C1 121.0(2) . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
O1 C6 C7 124.6(2) . . ?
O1 C6 C5 115.32(19) . . ?
C7 C6 C5 120.1(2) . . ?
C6 C7 C8 119.0(2) . . ?
C6 C7 H7A 120.5 . . ?
C8 C7 H7A 120.5 . . ?
C3 C8 C7 122.0(2) . . ?
C3 C8 H8A 119.0 . . ?
C7 C8 H8A 119.0 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.1(2) . . ?
C15 C10 C2 119.71(19) . . ?
C11 C10 C2 122.2(2) . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 H13A 120.4 . . ?
C12 C13 H13A 120.4 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C14 C15 C10 120.8(2) . . ?
C14 C15 H15A 119.6 . . ?
C10 C15 H15A 119.6 . . ?
O2 C16 O3 124.8(2) . . ?
O2 C16 C1 123.5(2) . . ?
O3 C16 C1 111.68(18) . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 O5 124.1(2) . . ?
O4 C18 C2 124.6(2) . . ?
O5 C18 C2 111.31(17) . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C3 C1 C2 C10 -168.2(2) . . . . ?
C16 C1 C2 C10 6.9(3) . . . . ?
C3 C1 C2 C18 12.3(3) . . . . ?
C16 C1 C2 C18 -172.55(19) . . . . ?
C2 C1 C3 C8 47.9(3) . . . . ?
C16 C1 C3 C8 -127.5(2) . . . . ?
C2 C1 C3 C4 -135.6(2) . . . . ?
C16 C1 C3 C4 49.0(3) . . . . ?
C8 C3 C4 C5 -1.2(3) . . . . ?
C1 C3 C4 C5 -177.9(2) . . . . ?
C3 C4 C5 C6 2.0(3) . . . . ?
C9 O1 C6 C7 -0.2(3) . . . . ?
C9 O1 C6 C5 -178.60(19) . . . . ?
C4 C5 C6 O1 177.22(19) . . . . ?
C4 C5 C6 C7 -1.3(3) . . . . ?
O1 C6 C7 C8 -178.62(19) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C4 C3 C8 C7 -0.3(3) . . . . ?
C1 C3 C8 C7 176.3(2) . . . . ?
C6 C7 C8 C3 1.1(3) . . . . ?
C1 C2 C10 C15 -140.8(2) . . . . ?
C18 C2 C10 C15 38.7(3) . . . . ?
C1 C2 C10 C11 39.8(3) . . . . ?
C18 C2 C10 C11 -140.7(2) . . . . ?
C15 C10 C11 C12 1.9(3) . . . . ?
C2 C10 C11 C12 -178.7(2) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C15 1.0(4) . . . . ?
C13 C14 C15 C10 0.1(3) . . . . ?
C11 C10 C15 C14 -1.5(3) . . . . ?
C2 C10 C15 C14 179.1(2) . . . . ?
C17 O3 C16 O2 6.1(3) . . . . ?
C17 O3 C16 C1 -175.42(18) . . . . ?
C2 C1 C16 O2 -131.1(2) . . . . ?
C3 C1 C16 O2 44.4(3) . . . . ?
C2 C1 C16 O3 50.4(3) . . . . ?
C3 C1 C16 O3 -134.07(19) . . . . ?
C19 O5 C18 O4 -1.4(3) . . . . ?
C19 O5 C18 C2 -179.42(18) . . . . ?
C1 C2 C18 O4 58.0(3) . . . . ?
C10 C2 C18 O4 -121.5(2) . . . . ?
C1 C2 C18 O5 -124.0(2) . . . . ?
C10 C2 C18 O5 56.4(2) . . . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.057

