# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_O20_004_Pna21
_database_code_depnum_ccdc_archive 'CCDC 2076253'
loop_
_audit_author_name
_audit_author_address
'Myoung Soo Lah'
;Ulsan National Institute of Science and Technology (UNIST)
South Korea
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'Ethyl (1S,2S,6S)-1-acetyl-2-hydroxy-5-oxo-6-(2-oxo-2-phenylethyl)cyclohex-3-ene-1-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 O6'
_chemical_formula_weight         344.35

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   21.521(4)
_cell_length_b                   11.299(2)
_cell_length_c                   6.7740(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1647.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    13398
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      27.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6682
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15743
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.893
_diffrn_reflns_theta_max         27.473
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3760
_reflns_number_gt                3218
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.999

_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       'Rigaku Rapid Auto'
_computing_cell_refinement       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0692P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1105 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3760
_refine_ls_number_parameters     307
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.32248(11) 0.0823(2) 0.2674(4) 0.0347(7) Uani 1 1 d . . . . .
C1 C 0.32339(14) 0.1297(3) 0.4281(6) 0.0238(7) Uani 1 1 d . . . . .
C2 C 0.26564(16) 0.1511(3) 0.5378(6) 0.0292(8) Uani 1 1 d . . . . .
H2 H 0.229(2) 0.129(3) 0.483(6) 0.034(11) Uiso 1 1 d . . . . .
C3 C 0.26530(15) 0.2032(3) 0.7126(5) 0.0269(8) Uani 1 1 d . . . . .
H3 H 0.2296(18) 0.213(3) 0.779(6) 0.031(10) Uiso 1 1 d . . . . .
O2 O 0.30728(11) 0.3434(2) 0.9359(4) 0.0286(6) Uani 1 1 d . . . . .
H1O H 0.327(2) 0.343(4) 1.022(7) 0.029(12) Uiso 1 1 d . . . . .
C4 C 0.32296(13) 0.2467(3) 0.8129(5) 0.0207(7) Uani 1 1 d . . . . .
H4 H 0.3396(18) 0.184(4) 0.897(6) 0.034(11) Uiso 1 1 d . . . . .
C5 C 0.37298(12) 0.2787(3) 0.6553(5) 0.0168(6) Uani 1 1 d . . . . .
C6 C 0.38392(13) 0.1642(3) 0.5324(5) 0.0202(7) Uani 1 1 d . . . . .
H6 H 0.3862(18) 0.098(4) 0.618(7) 0.034(11) Uiso 1 1 d . . . . .
O3 O 0.44041(10) 0.3019(2) 0.9390(4) 0.0303(6) Uani 1 1 d . . . . .
O4 O 0.47016(10) 0.3769(2) 0.6472(4) 0.0290(6) Uani 1 1 d . . . . .
C7 C 0.43139(13) 0.3177(3) 0.7674(5) 0.0198(7) Uani 1 1 d . . . . .
C8 C 0.5267(2) 0.4282(7) 0.7323(8) 0.0603(18) Uani 1 1 d . . . . .
H81 H 0.527(2) 0.432(5) 0.862(8) 0.053(14) Uiso 1 1 d . . . . .
H82 H 0.536(3) 0.356(5) 0.793(10) 0.07(2) Uiso 1 1 d . . . . .
C9 C 0.57911(17) 0.4094(4) 0.6012(7) 0.0365(10) Uani 1 1 d . . . . .
H91 H 0.6164(19) 0.443(3) 0.652(6) 0.030(10) Uiso 1 1 d . . . . .
H92 H 0.578(3) 0.413(6) 0.467(12) 0.10(2) Uiso 1 1 d . . . . .
H93 H 0.595(4) 0.330(9) 0.600(14) 0.14(3) Uiso 1 1 d . . . . .
O5 O 0.34292(11) 0.3624(2) 0.3466(4) 0.0267(6) Uani 1 1 d . . . . .
C10 C 0.35110(13) 0.3805(3) 0.5196(5) 0.0197(7) Uani 1 1 d . . . . .
C11 C 0.33857(18) 0.4999(3) 0.6065(6) 0.0306(8) Uani 1 1 d . . . . .
H111 H 0.295(2) 0.500(4) 0.661(8) 0.062(14) Uiso 1 1 d . . . . .
H112 H 0.362(2) 0.519(5) 0.723(9) 0.061(15) Uiso 1 1 d . . . . .
H113 H 0.341(2) 0.556(5) 0.509(9) 0.072(17) Uiso 1 1 d . . . . .
C12 C 0.43911(14) 0.1628(3) 0.3911(5) 0.0211(7) Uani 1 1 d . . . . .
H121 H 0.4283(18) 0.099(4) 0.297(6) 0.036(11) Uiso 1 1 d . . . . .
H122 H 0.4435(17) 0.237(4) 0.326(6) 0.032(10) Uiso 1 1 d . . . . .
O6 O 0.50249(11) 0.1081(2) 0.6650(4) 0.0311(6) Uani 1 1 d . . . . .
C13 C 0.50000(13) 0.1313(3) 0.4895(5) 0.0198(7) Uani 1 1 d . . . . .
C14 C 0.55753(14) 0.1296(3) 0.3661(5) 0.0195(7) Uani 1 1 d . . . . .
C15 C 0.55767(16) 0.1607(3) 0.1674(5) 0.0256(7) Uani 1 1 d . . . . .
H15 H 0.5241(18) 0.181(3) 0.101(6) 0.027(9) Uiso 1 1 d . . . . .
C16 C 0.61319(17) 0.1620(3) 0.0635(6) 0.0326(9) Uani 1 1 d . . . . .
H16 H 0.616(2) 0.187(4) -0.071(8) 0.049(13) Uiso 1 1 d . . . . .
C17 C 0.66831(16) 0.1328(3) 0.1540(7) 0.0330(9) Uani 1 1 d . . . . .
H17 H 0.706(2) 0.135(4) 0.088(7) 0.041(12) Uiso 1 1 d . . . . .
C18 C 0.66836(15) 0.0991(3) 0.3500(6) 0.0302(8) Uani 1 1 d . . . . .
H18 H 0.705(2) 0.075(4) 0.410(7) 0.041(12) Uiso 1 1 d . . . . .
C19 C 0.61335(15) 0.0969(3) 0.4567(6) 0.0234(7) Uani 1 1 d . . . . .
H19 H 0.6136(16) 0.076(3) 0.592(6) 0.022(9) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.213(4) . ?
C1 C2 1.468(5) . ?
C1 C6 1.532(4) . ?
C2 C3 1.322(5) . ?
C2 H2 0.90(4) . ?
C3 C4 1.497(5) . ?
C3 H3 0.90(4) . ?
O2 C4 1.415(4) . ?
O2 H1O 0.72(5) . ?
C4 C5 1.559(4) . ?
C4 H4 0.98(4) . ?
C5 C7 1.533(4) . ?
C5 C10 1.546(4) . ?
C5 C6 1.557(4) . ?
C6 C12 1.525(4) . ?
C6 H6 0.95(5) . ?
O3 C7 1.192(4) . ?
O4 C7 1.344(4) . ?
O4 C8 1.465(5) . ?
C8 C9 1.452(6) . ?
C8 H81 0.88(6) . ?
C8 H82 0.94(5) . ?
C9 H91 0.95(4) . ?
C9 H92 0.91(8) . ?
C9 H93 0.96(10) . ?
O5 C10 1.202(4) . ?
C10 C11 1.496(5) . ?
C11 H111 1.00(5) . ?
C11 H112 0.95(6) . ?
C11 H113 0.92(6) . ?
C12 C13 1.513(4) . ?
C12 H121 0.99(4) . ?
C12 H122 0.95(4) . ?
O6 C13 1.219(4) . ?
C13 C14 1.494(4) . ?
C14 C15 1.391(5) . ?
C14 C19 1.398(4) . ?
C15 C16 1.387(5) . ?
C15 H15 0.88(4) . ?
C16 C17 1.375(6) . ?
C16 H16 0.96(5) . ?
C17 C18 1.381(6) . ?
C17 H17 0.93(5) . ?
C18 C19 1.387(5) . ?
C18 H18 0.92(4) . ?
C19 H19 0.95(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
O1 C1 C2 120.9(3) . . ?
O1 C1 C6 122.6(3) . . ?
C2 C1 C6 116.4(3) . . ?
C3 C2 C1 122.1(3) . . ?
C3 C2 H2 119(3) . . ?
C1 C2 H2 119(3) . . ?
C2 C3 C4 123.2(3) . . ?
C2 C3 H3 121(3) . . ?
C4 C3 H3 116(3) . . ?
C4 O2 H1O 109(4) . . ?
O2 C4 C3 108.8(2) . . ?
O2 C4 C5 112.9(3) . . ?
C3 C4 C5 109.8(3) . . ?
O2 C4 H4 108(2) . . ?
C3 C4 H4 109(2) . . ?
C5 C4 H4 108(2) . . ?
C7 C5 C10 109.3(2) . . ?
C7 C5 C6 112.3(2) . . ?
C10 C5 C6 110.3(3) . . ?
C7 C5 C4 107.1(2) . . ?
C10 C5 C4 111.7(2) . . ?
C6 C5 C4 106.1(2) . . ?
C12 C6 C1 111.7(3) . . ?
C12 C6 C5 117.5(3) . . ?
C1 C6 C5 109.2(2) . . ?
C12 C6 H6 110(2) . . ?
C1 C6 H6 97(2) . . ?
C5 C6 H6 110(3) . . ?
C7 O4 C8 118.3(3) . . ?
O3 C7 O4 124.4(3) . . ?
O3 C7 C5 125.0(3) . . ?
O4 C7 C5 110.6(3) . . ?
C9 C8 O4 110.3(4) . . ?
C9 C8 H81 128(3) . . ?
O4 C8 H81 115(3) . . ?
C9 C8 H82 88(4) . . ?
O4 C8 H82 91(4) . . ?
H81 C8 H82 67(4) . . ?
C8 C9 H91 112(2) . . ?
C8 C9 H92 125(4) . . ?
H91 C9 H92 112(5) . . ?
C8 C9 H93 114(5) . . ?
H91 C9 H93 95(5) . . ?
H92 C9 H93 92(6) . . ?
O5 C10 C11 120.7(3) . . ?
O5 C10 C5 119.9(3) . . ?
C11 C10 C5 119.4(3) . . ?
C10 C11 H111 108(3) . . ?
C10 C11 H112 116(3) . . ?
H111 C11 H112 100(4) . . ?
C10 C11 H113 109(4) . . ?
H111 C11 H113 109(4) . . ?
H112 C11 H113 114(5) . . ?
C13 C12 C6 113.6(3) . . ?
C13 C12 H121 109(2) . . ?
C6 C12 H121 103(2) . . ?
C13 C12 H122 109(2) . . ?
C6 C12 H122 111(2) . . ?
H121 C12 H122 111(3) . . ?
O6 C13 C14 120.4(3) . . ?
O6 C13 C12 121.3(3) . . ?
C14 C13 C12 118.3(3) . . ?
C15 C14 C19 119.3(3) . . ?
C15 C14 C13 122.7(3) . . ?
C19 C14 C13 118.0(3) . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 116(3) . . ?
C14 C15 H15 124(3) . . ?
C17 C16 C15 121.0(4) . . ?
C17 C16 H16 117(3) . . ?
C15 C16 H16 122(3) . . ?
C16 C17 C18 119.7(3) . . ?
C16 C17 H17 122(3) . . ?
C18 C17 H17 118(3) . . ?
C17 C18 C19 120.3(4) . . ?
C17 C18 H18 120(3) . . ?
C19 C18 H18 119(3) . . ?
C18 C19 C14 120.0(3) . . ?
C18 C19 H19 120(2) . . ?
C14 C19 H19 120(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H1O O3 0.72(5) 2.54(4) 2.903(3) 113(4) . yes
O2 H1O O5 0.72(5) 2.24(5) 2.894(4) 152(4) 1_556 yes

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.059






















_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_O20_006_P21
_database_code_depnum_ccdc_archive 'CCDC 2076252'
loop_
_audit_author_name
_audit_author_address
'Myoung Soo Lah'
;Ulsan National Institute of Science and Technology (UNIST)
South Korea
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'Ethyl (1R,2S,6S)-1-acetyl-2-hydroxy-6-(2-(naphthalen-2-yl)-2-oxoethyl)-5-oxocyclohex-3-ene-1-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C92 H88 O24 (C23 H22 O6)'
_chemical_formula_weight         1577.62

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   7.6292(15)
_cell_length_b                   18.955(4)
_cell_length_c                   27.164(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.56(3)
_cell_angle_gamma                90
_cell_volume                     3926.7(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    22857
_cell_measurement_theta_min      2.995
_cell_measurement_theta_max      27.595

_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             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5514
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38414
_diffrn_reflns_av_unetI/netI     0.1973
_diffrn_reflns_av_R_equivalents  0.1575
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.994
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.930
_reflns_number_total             16439
_reflns_number_gt                8364
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_max     0.823
_reflns_Friedel_fraction_full    0.859

_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       'Rigaku Rapid Auto'
_computing_cell_refinement       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.1081P)²+3.7016P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2069 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.9(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         16439
_refine_ls_number_parameters     1059
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2201
_refine_ls_R_factor_gt           0.1254
_refine_ls_wR_factor_ref         0.2908
_refine_ls_wR_factor_gt          0.2485
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.003
_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 0.3320(13) 0.6550(4) 0.4591(3) 0.056(2) Uani 1 1 d . . . . .
C1 C 0.4052(17) 0.5995(6) 0.4511(3) 0.040(3) Uani 1 1 d . . . . .
C2 C 0.3386(18) 0.5321(6) 0.4679(4) 0.044(3) Uani 1 1 d . . . . .
H2 H 0.236772 0.531113 0.485993 0.053 Uiso 1 1 calc R U . . .
C3 C 0.4185(16) 0.4728(6) 0.4582(4) 0.039(3) Uani 1 1 d . . . . .
H3 H 0.368779 0.430856 0.468820 0.047 Uiso 1 1 calc R U . . .
O2 O 0.6151(11) 0.4017(4) 0.4113(3) 0.040(2) Uani 1 1 d . . . . .
H2O H 0.531999 0.390407 0.393197 0.060 Uiso 1 1 calc R U . . .
C4 C 0.5848(14) 0.4694(5) 0.4311(3) 0.027(2) Uani 1 1 d . . . . .
H4 H 0.679392 0.477786 0.455546 0.032 Uiso 1 1 calc R U . . .
C5 C 0.5924(13) 0.5304(5) 0.3942(3) 0.024(2) Uani 1 1 d . . . . .
C6 C 0.5778(16) 0.5994(5) 0.4250(4) 0.033(3) Uani 1 1 d . . . . .
H6 H 0.671561 0.598194 0.450402 0.040 Uiso 1 1 calc R U . . .
O3 O 0.3415(10) 0.5722(4) 0.3474(3) 0.0367(19) Uani 1 1 d . . . . .
O4 O 0.4409(9) 0.4636(3) 0.3330(2) 0.0311(17) Uani 1 1 d . . . . .
C7 C 0.4421(14) 0.5265(6) 0.3559(4) 0.029(2) Uani 1 1 d . . . . .
C8 C 0.3096(16) 0.4571(6) 0.2941(4) 0.038(3) Uani 1 1 d . . . . .
H8A H 0.326650 0.492885 0.269214 0.045 Uiso 1 1 calc R U . . .
H8B H 0.193316 0.462790 0.307178 0.045 Uiso 1 1 calc R U . . .
C9 C 0.3290(17) 0.3848(7) 0.2724(4) 0.053(4) Uani 1 1 d . . . . .
H9A H 0.442848 0.380491 0.258445 0.080 Uiso 1 1 calc R U . . .
H9B H 0.240391 0.377763 0.247088 0.080 Uiso 1 1 calc R U . . .
H9C H 0.316341 0.349946 0.297662 0.080 Uiso 1 1 calc R U . . .
O5 O 0.7702(12) 0.5421(5) 0.3240(3) 0.053(2) Uani 1 1 d . . . . .
C10 C 0.7678(15) 0.5305(5) 0.3679(4) 0.033(3) Uani 1 1 d . . . . .
C11 C 0.9303(17) 0.5210(9) 0.3970(6) 0.070(4) Uani 1 1 d . . . . .
H11A H 1.028971 0.527799 0.376343 0.105 Uiso 1 1 calc R U . . .
H11B H 0.933785 0.474118 0.410448 0.105 Uiso 1 1 calc R U . . .
H11C H 0.934819 0.554728 0.423359 0.105 Uiso 1 1 calc R U . . .
C12 C 0.5986(15) 0.6689(5) 0.3957(3) 0.027(2) Uani 1 1 d . . . . .
H12A H 0.681846 0.661521 0.369819 0.032 Uiso 1 1 calc R U . . .
H12B H 0.486718 0.681280 0.380180 0.032 Uiso 1 1 calc R U . . .
O6 O 0.7136(14) 0.7191(4) 0.4695(3) 0.062(3) Uani 1 1 d . . . . .
C13 C 0.6605(16) 0.7290(6) 0.4277(4) 0.039(3) Uani 1 1 d . . . . .
C14 C 0.6576(13) 0.8017(5) 0.4069(4) 0.026(2) Uani 1 1 d . . . . .
C15 C 0.5846(14) 0.8162(6) 0.3611(4) 0.033(3) Uani 1 1 d . . . . .
H15 H 0.535995 0.779555 0.342531 0.040 Uiso 1 1 calc R U . . .
C16 C 0.5815(16) 0.8847(6) 0.3417(4) 0.039(3) Uani 1 1 d . . . . .
C17 C 0.5145(19) 0.9004(7) 0.2944(5) 0.059(4) Uani 1 1 d . . . . .
H17 H 0.465218 0.864593 0.275097 0.070 Uiso 1 1 calc R U . . .
C18 C 0.520(2) 0.9655(9) 0.2766(6) 0.072(4) Uani 1 1 d . . . . .
H18 H 0.476061 0.974479 0.245018 0.086 Uiso 1 1 calc R U . . .
C19 C 0.5936(19) 1.0222(8) 0.3054(6) 0.066(4) Uani 1 1 d . . . . .
H19 H 0.599684 1.067286 0.292071 0.079 Uiso 1 1 calc R U . . .
C20 C 0.6530(18) 1.0103(6) 0.3513(5) 0.049(3) Uani 1 1 d . . . . .
H20 H 0.695378 1.047718 0.370286 0.058 Uiso 1 1 calc R U . . .
C21 C 0.6525(16) 0.9408(6) 0.3716(4) 0.038(3) Uani 1 1 d . . . . .
C22 C 0.7227(15) 0.9220(5) 0.4178(4) 0.030(2) Uani 1 1 d . . . . .
H22 H 0.771511 0.957568 0.437345 0.036 Uiso 1 1 calc R U . . .
C23 C 0.7245(15) 0.8580(6) 0.4354(3) 0.034(3) Uani 1 1 d . . . . .
H23 H 0.770202 0.849522 0.466945 0.040 Uiso 1 1 calc R U . . .
O31 O -0.1079(16) 0.0954(6) 0.4432(4) 0.093(4) Uani 1 1 d . . . . .
C31 C -0.0245(19) 0.1484(6) 0.4381(4) 0.048(3) Uani 1 1 d . . . . .
C32 C -0.082(2) 0.2172(8) 0.4534(4) 0.061(4) Uani 1 1 d . . . . .
H32 H -0.188582 0.220756 0.468966 0.073 Uiso 1 1 calc R U . . .
C33 C 0.0094(18) 0.2761(7) 0.4464(4) 0.049(3) Uani 1 1 d . . . . .
H33 H -0.033837 0.319034 0.457324 0.059 Uiso 1 1 calc R U . . .
O32 O 0.2250(12) 0.3398(4) 0.3988(3) 0.048(2) Uani 1 1 d . . . . .
H32O H 0.144535 0.352446 0.380245 0.072 Uiso 1 1 calc R U . . .
C34 C 0.1801(18) 0.2737(6) 0.4213(4) 0.042(3) Uani 1 1 d . . . . .
H34 H 0.270459 0.264079 0.446772 0.050 Uiso 1 1 calc R U . . .
C35 C 0.1818(15) 0.2108(6) 0.3848(4) 0.035(3) Uani 1 1 d . . . . .
C36 C 0.1564(16) 0.1439(6) 0.4149(4) 0.040(3) Uani 1 1 d . . . . .
H36 H 0.242858 0.145845 0.442260 0.048 Uiso 1 1 calc R U . . .
O33 O -0.0460(14) 0.1693(4) 0.3300(3) 0.057(3) Uani 1 1 d . . . . .
O34 O 0.0169(11) 0.2815(4) 0.3287(3) 0.042(2) Uani 1 1 d . . . . .
C37 C 0.0377(15) 0.2167(5) 0.3444(3) 0.028(2) Uani 1 1 d . . . . .
C38 C -0.1078(19) 0.2938(7) 0.2895(5) 0.057(4) Uani 1 1 d . . . . .
H38A H -0.209286 0.263648 0.293463 0.068 Uiso 1 1 calc R U . . .
H38B H -0.056098 0.282538 0.258227 0.068 Uiso 1 1 calc R U . . .
C39 C -0.1631(18) 0.3699(7) 0.2900(5) 0.058(4) Uani 1 1 d . . . . .
H39A H -0.222041 0.379776 0.319984 0.087 Uiso 1 1 calc R U . . .
H39B H -0.240987 0.378963 0.262376 0.087 Uiso 1 1 calc R U . . .
H39C H -0.061416 0.399463 0.287923 0.087 Uiso 1 1 calc R U . . .
O35 O 0.3612(17) 0.2038(6) 0.3139(5) 0.095(4) Uani 1 1 d . . . . .
C40 C 0.3563(18) 0.2072(6) 0.3578(8) 0.067(5) Uani 1 1 d . . . . .
C41 C 0.5323(19) 0.2063(8) 0.3871(8) 0.104(7) Uani 1 1 d . . . . .
H41A H 0.626669 0.199900 0.364828 0.156 Uiso 1 1 calc R U . . .
H41B H 0.532365 0.168124 0.410345 0.156 Uiso 1 1 calc R U . . .
H41C H 0.547519 0.250134 0.404323 0.156 Uiso 1 1 calc R U . . .
C42 C 0.1819(16) 0.0743(6) 0.3900(4) 0.039(3) Uani 1 1 d . . . . .
H42A H 0.078869 0.064123 0.369499 0.047 Uiso 1 1 calc R U . . .
H42B H 0.281078 0.078008 0.368521 0.047 Uiso 1 1 calc R U . . .
O36 O 0.261(2) 0.0269(5) 0.4664(4) 0.111(5) Uani 1 1 d . . . . .
C43 C 0.213(2) 0.0145(6) 0.4244(4) 0.050(4) Uani 1 1 d . . . . .
C44 C 0.1832(14) -0.0593(5) 0.4082(4) 0.030(2) Uani 1 1 d . . . . .
C45 C 0.1151(15) -0.0751(5) 0.3618(4) 0.034(3) Uani 1 1 d . . . . .
H45 H 0.092924 -0.038869 0.339458 0.041 Uiso 1 1 calc R U . . .
C46 C 0.0787(14) -0.1456(6) 0.3480(3) 0.031(3) Uani 1 1 d . . . . .
C47 C 0.0104(16) -0.1629(7) 0.3016(4) 0.042(3) Uani 1 1 d . . . . .
H47 H -0.010376 -0.127390 0.278555 0.051 Uiso 1 1 calc R U . . .
C48 C -0.0268(17) -0.2313(6) 0.2892(4) 0.043(3) Uani 1 1 d . . . . .
H48 H -0.080872 -0.241625 0.259006 0.051 Uiso 1 1 calc R U . . .
C49 C 0.0170(17) -0.2863(7) 0.3226(4) 0.046(3) Uani 1 1 d . . . . .
H49 H -0.005317 -0.332904 0.313797 0.055 Uiso 1 1 calc R U . . .
C50 C 0.0928(15) -0.2710(6) 0.3680(4) 0.038(3) Uani 1 1 d . . . . .
H50 H 0.122867 -0.307330 0.389626 0.045 Uiso 1 1 calc R U . . .
C51 C 0.1250(15) -0.1996(6) 0.3819(4) 0.036(3) Uani 1 1 d . . . . .
C52 C 0.1954(17) -0.1835(5) 0.4281(4) 0.039(3) Uani 1 1 d . . . . .
H52 H 0.221274 -0.219591 0.450393 0.047 Uiso 1 1 calc R U . . .
C53 C 0.2270(17) -0.1148(6) 0.4412(4) 0.047(3) Uani 1 1 d . . . . .
H53 H 0.277601 -0.104533 0.471859 0.056 Uiso 1 1 calc R U . . .
O61 O -0.0958(14) 0.3576(6) 0.0513(3) 0.074(3) Uani 1 1 d . . . . .
C61 C -0.0102(18) 0.4101(6) 0.0589(4) 0.040(3) Uani 1 1 d . . . . .
C62 C -0.0757(19) 0.4817(8) 0.0452(4) 0.055(4) Uani 1 1 d . . . . .
H62 H -0.185116 0.486067 0.029549 0.066 Uiso 1 1 calc R U . . .
C63 C 0.0174(17) 0.5391(7) 0.0548(4) 0.049(3) Uani 1 1 d . . . . .
H63 H -0.030586 0.582550 0.045916 0.059 Uiso 1 1 calc R U . . .
O62 O 0.2396(13) 0.6018(4) 0.1010(3) 0.054(2) Uani 1 1 d . . . . .
H62O H 0.172094 0.610433 0.123134 0.081 Uiso 1 1 calc R U . . .
C64 C 0.1925(15) 0.5380(6) 0.0786(4) 0.036(3) Uani 1 1 d . . . . .
H64 H 0.275788 0.530342 0.052278 0.043 Uiso 1 1 calc R U . . .
C65 C 0.2083(14) 0.4721(5) 0.1134(3) 0.025(2) Uani 1 1 d . . . . .
C66 C 0.1740(15) 0.4079(5) 0.0820(3) 0.031(3) Uani 1 1 d . . . . .
H66 H 0.256554 0.409475 0.054992 0.037 Uiso 1 1 calc R U . . .
O63 O -0.0056(13) 0.4279(5) 0.1695(3) 0.058(3) Uani 1 1 d . . . . .
O64 O 0.0655(14) 0.5411(4) 0.1731(3) 0.066(3) Uani 1 1 d . . . . .
C67 C 0.0757(16) 0.4761(6) 0.1551(4) 0.036(3) Uani 1 1 d . . . . .
C68 C -0.059(3) 0.5506(8) 0.2139(6) 0.091(7) Uani 1 1 d . . . . .
H68 H -0.062616 0.521793 0.241548 0.109 Uiso 1 1 calc R U . . .
C69 C -0.161(2) 0.6040(13) 0.2059(6) 0.128(10) Uani 1 1 d . . . . .
H69A H -0.150864 0.630663 0.177367 0.153 Uiso 1 1 calc R U . . .
H69B H -0.245544 0.615704 0.228612 0.153 Uiso 1 1 calc R U . . .
O65 O 0.4178(13) 0.4732(6) 0.1805(3) 0.068(3) Uani 1 1 d . . . . .
C70 C 0.3949(14) 0.4709(5) 0.1354(4) 0.033(3) Uani 1 1 d . . . . .
C71 C 0.5431(16) 0.4671(8) 0.1033(5) 0.057(4) Uani 1 1 d . . . . .
H71A H 0.554332 0.510896 0.085924 0.086 Uiso 1 1 calc R U . . .
H71B H 0.525055 0.429443 0.079998 0.086 Uiso 1 1 calc R U . . .
H71C H 0.648116 0.458289 0.122555 0.086 Uiso 1 1 calc R U . . .
C72 C 0.2001(16) 0.3365(6) 0.1082(4) 0.036(3) Uani 1 1 d . . . . .
H72A H 0.301050 0.339937 0.130532 0.043 Uiso 1 1 calc R U . . .
H72B H 0.098307 0.326980 0.127704 0.043 Uiso 1 1 calc R U . . .
O66 O 0.2676(16) 0.2861(4) 0.0322(3) 0.078(4) Uani 1 1 d . . . . .
C73 C 0.2265(16) 0.2766(6) 0.0743(4) 0.037(3) Uani 1 1 d . . . . .
C74 C 0.2050(14) 0.2035(5) 0.0934(4) 0.030(3) Uani 1 1 d . . . . .
C75 C 0.1430(13) 0.1894(6) 0.1392(4) 0.032(3) Uani 1 1 d . . . . .
H75 H 0.116756 0.226709 0.159993 0.038 Uiso 1 1 calc R U . . .
C76 C 0.1179(14) 0.1193(6) 0.1557(4) 0.031(2) Uani 1 1 d . . . . .
C77 C 0.0557(16) 0.1038(7) 0.2036(4) 0.045(3) Uani 1 1 d . . . . .
H77 H 0.028723 0.140265 0.225072 0.054 Uiso 1 1 calc R U . . .
C78 C 0.0358(19) 0.0348(7) 0.2179(5) 0.059(4) Uani 1 1 d . . . . .
H78 H -0.007951 0.024695 0.248759 0.071 Uiso 1 1 calc R U . . .
C79 C 0.0800(19) -0.0198(6) 0.1870(4) 0.052(4) Uani 1 1 d . . . . .
H79 H 0.068388 -0.066120 0.197757 0.063 Uiso 1 1 calc R U . . .
C80 C 0.1405(16) -0.0074(6) 0.1409(5) 0.046(3) Uani 1 1 d . . . . .
H80 H 0.166804 -0.045123 0.120485 0.055 Uiso 1 1 calc R U . . .
C81 C 0.1634(14) 0.0624(6) 0.1241(4) 0.036(3) Uani 1 1 d . . . . .
C82 C 0.2229(15) 0.0775(5) 0.0772(4) 0.035(3) Uani 1 1 d . . . . .
H82 H 0.247830 0.040732 0.055859 0.042 Uiso 1 1 calc R U . . .
C83 C 0.2455(15) 0.1460(5) 0.0620(4) 0.033(3) Uani 1 1 d . . . . .
H83 H 0.287620 0.154930 0.030794 0.039 Uiso 1 1 calc R U . . .
O91 O 0.3600(15) 0.9159(5) 0.0431(4) 0.074(3) Uani 1 1 d . . . . .
C91 C 0.4314(18) 0.8593(7) 0.0521(4) 0.048(3) Uani 1 1 d . . . . .
C92 C 0.3505(17) 0.7935(6) 0.0335(4) 0.044(3) Uani 1 1 d . . . . .
H92 H 0.247552 0.794798 0.014425 0.053 Uiso 1 1 calc R U . . .
C93 C 0.4268(18) 0.7328(6) 0.0445(4) 0.045(3) Uani 1 1 d . . . . .
H93 H 0.367176 0.691652 0.035668 0.054 Uiso 1 1 calc R U . . .
O92 O 0.6236(13) 0.6572(4) 0.0900(3) 0.048(2) Uani 1 1 d . . . . .
H92O H 0.534(15) 0.660(5) 0.109(4) 0.03(3) Uiso 1 1 d . . . . .
C94 C 0.5958(15) 0.7255(5) 0.0690(4) 0.028(2) Uani 1 1 d . . . . .
H94 H 0.685414 0.732778 0.044360 0.034 Uiso 1 1 calc R U . . .
C95 C 0.6151(15) 0.7861(6) 0.1078(3) 0.034(3) Uani 1 1 d . . . . .
C96 C 0.6036(14) 0.8543(5) 0.0776(3) 0.024(2) Uani 1 1 d . . . . .
H96 H 0.691165 0.850584 0.051971 0.028 Uiso 1 1 calc R U . . .
O93 O 0.3832(14) 0.8329(5) 0.1546(3) 0.061(3) Uani 1 1 d . . . . .
O94 O 0.4659(11) 0.7224(4) 0.1677(2) 0.043(2) Uani 1 1 d . . . . .
C97 C 0.4742(17) 0.7829(6) 0.1449(4) 0.038(3) Uani 1 1 d . . . . .
C98 C 0.3367(19) 0.7176(8) 0.2068(4) 0.063(4) Uani 1 1 d . . . . .
H98A H 0.324275 0.763128 0.222594 0.076 Uiso 1 1 calc R U . . .
H98B H 0.223377 0.703994 0.192737 0.076 Uiso 1 1 calc R U . . .
C99 C 0.393(3) 0.6674(13) 0.2414(7) 0.143(11) Uani 1 1 d . . . . .
H99A H 0.391431 0.621452 0.226498 0.214 Uiso 1 1 calc R U . . .
H99B H 0.317109 0.667886 0.268887 0.214 Uiso 1 1 calc R U . . .
H99C H 0.510813 0.678380 0.252497 0.214 Uiso 1 1 calc R U . . .
O95 O 0.8084(15) 0.7922(6) 0.1785(4) 0.081(3) Uani 1 1 d . . . . .
C100 C 0.7991(18) 0.7831(6) 0.1340(5) 0.050(3) Uani 1 1 d . . . . .
C101 C 0.9547(19) 0.7714(9) 0.1039(7) 0.084(5) Uani 1 1 d . . . . .
H10B H 0.938085 0.794325 0.072608 0.126 Uiso 1 1 calc R U . . .
H10A H 0.970739 0.721721 0.098932 0.126 Uiso 1 1 calc R U . . .
H10C H 1.056415 0.790585 0.120633 0.126 Uiso 1 1 calc R U . . .
C102 C 0.6435(17) 0.9240(5) 0.1062(4) 0.036(3) Uani 1 1 d . . . . .
H10E H 0.539083 0.938909 0.122947 0.043 Uiso 1 1 calc R U . . .
H10D H 0.734800 0.915266 0.131025 0.043 Uiso 1 1 calc R U . . .
O96 O 0.7512(15) 0.9691(4) 0.0314(3) 0.068(3) Uani 1 1 d . . . . .
C103 C 0.7017(15) 0.9824(6) 0.0724(4) 0.032(3) Uani 1 1 d . . . . .
C104 C 0.6988(14) 1.0558(5) 0.0909(3) 0.027(2) Uani 1 1 d . . . . .
C105 C 0.6260(15) 1.0726(6) 0.1352(3) 0.032(3) Uani 1 1 d . . . . .
H105 H 0.579625 1.037197 0.154649 0.038 Uiso 1 1 calc R U . . .
C106 C 0.6215(14) 1.1439(6) 0.1513(3) 0.030(2) Uani 1 1 d . . . . .
C107 C 0.5532(14) 1.1645(6) 0.1960(3) 0.030(2) Uani 1 1 d . . . . .
H107 H 0.512493 1.130399 0.217471 0.036 Uiso 1 1 calc R U . . .
C108 C 0.5450(18) 1.2335(7) 0.2086(4) 0.050(3) Uani 1 1 d . . . . .
H108 H 0.492277 1.246183 0.237721 0.060 Uiso 1 1 calc R U . . .
C109 C 0.6138(18) 1.2859(6) 0.1788(4) 0.047(3) Uani 1 1 d . . . . .
H109 H 0.609969 1.332747 0.188785 0.056 Uiso 1 1 calc R U . . .
C110 C 0.6880(15) 1.2686(6) 0.1345(4) 0.038(3) Uani 1 1 d . . . . .
H110 H 0.736276 1.303548 0.115063 0.045 Uiso 1 1 calc R U . . .
C111 C 0.6898(14) 1.1975(5) 0.1190(4) 0.030(2) Uani 1 1 d . . . . .
C112 C 0.7578(16) 1.1755(6) 0.0735(4) 0.036(3) Uani 1 1 d . . . . .
H112 H 0.798192 1.209404 0.051805 0.043 Uiso 1 1 calc R U . . .
C113 C 0.7655(15) 1.1083(5) 0.0609(4) 0.033(3) Uani 1 1 d . . . . .
H113 H 0.816544 1.095899 0.031396 0.039 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.213(13) . ?
C1 C2 1.453(16) . ?
C1 C6 1.513(17) . ?
C2 C3 1.309(16) . ?
C2 H2 0.9300 . ?
C3 C4 1.486(15) . ?
C3 H3 0.9300 . ?
O2 C4 1.413(12) . ?
O2 H2O 0.8200 . ?
C4 C5 1.534(13) . ?
C4 H4 0.9800 . ?
C5 C7 1.529(15) . ?
C5 C10 1.534(15) . ?
C5 C6 1.558(13) . ?
C6 C12 1.551(14) . ?
C6 H6 0.9800 . ?
O3 C7 1.176(12) . ?
O4 C7 1.344(12) . ?
O4 C8 1.440(12) . ?
C8 C9 1.501(16) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
O5 C10 1.214(12) . ?
C10 C11 1.463(17) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.501(15) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O6 C13 1.211(12) . ?
C13 C14 1.489(15) . ?
C14 C15 1.377(14) . ?
C14 C23 1.406(14) . ?
C15 C16 1.400(15) . ?
C15 H15 0.9300 . ?
C16 C17 1.403(16) . ?
C16 C21 1.435(16) . ?
C17 C18 1.325(19) . ?
C17 H17 0.9300 . ?
C18 C19 1.43(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.334(18) . ?
C19 H19 0.9300 . ?
C20 C21 1.427(15) . ?
C20 H20 0.9300 . ?
C21 C22 1.398(15) . ?
C22 C23 1.304(14) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
O31 C31 1.199(14) . ?
C31 C32 1.442(18) . ?
C31 C36 1.534(18) . ?
C32 C33 1.332(17) . ?
C32 H32 0.9300 . ?
C33 C34 1.487(18) . ?
C33 H33 0.9300 . ?
O32 C34 1.439(13) . ?
O32 H32O 0.8200 . ?
C34 C35 1.551(16) . ?
C34 H34 0.9800 . ?
C35 C36 1.524(14) . ?
C35 C37 1.537(15) . ?
C35 C40 1.540(19) . ?
C36 C42 1.499(16) . ?
C36 H36 0.9800 . ?
O33 C37 1.164(12) . ?
O34 C37 1.307(12) . ?
O34 C38 1.428(14) . ?
C38 C39 1.503(17) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
O35 C40 1.20(2) . ?
C40 C41 1.54(2) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 C43 1.483(15) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
O36 C43 1.213(14) . ?
C43 C44 1.482(15) . ?
C44 C45 1.383(14) . ?
C44 C53 1.415(15) . ?
C45 C46 1.413(15) . ?
C45 H45 0.9300 . ?
C46 C47 1.390(15) . ?
C46 C51 1.417(15) . ?
C47 C48 1.366(16) . ?
C47 H47 0.9300 . ?
C48 C49 1.415(17) . ?
C48 H48 0.9300 . ?
C49 C50 1.380(16) . ?
C49 H49 0.9300 . ?
C50 C51 1.424(16) . ?
C50 H50 0.9300 . ?
C51 C52 1.385(15) . ?
C52 C53 1.370(16) . ?
C52 H52 0.9300 . ?
C53 H53 0.9300 . ?
O61 C61 1.205(14) . ?
C61 C62 1.489(18) . ?
C61 C66 1.524(17) . ?
C62 C63 1.322(19) . ?
C62 H62 0.9300 . ?
C63 C64 1.469(17) . ?
C63 H63 0.9300 . ?
O62 C64 1.396(13) . ?
O62 H62O 0.8200 . ?
C64 C65 1.570(15) . ?
C64 H64 0.9800 . ?
C65 C66 1.505(14) . ?
C65 C70 1.528(15) . ?
C65 C67 1.541(14) . ?
C66 C72 1.538(14) . ?
C66 H66 0.9800 . ?
O63 C67 1.177(13) . ?
O64 C67 1.327(14) . ?
O64 C68 1.490(14) . ?
C68 C69 1.29(2) . ?
C68 H68 0.9300 . ?
C69 H69A 0.9300 . ?
C69 H69B 0.9300 . ?
O65 C70 1.233(13) . ?
C70 C71 1.449(16) . ?
C71 H71A 0.9600 . ?
C71 H71B 0.9600 . ?
C71 H71C 0.9600 . ?
C72 C73 1.479(14) . ?
C72 H72A 0.9700 . ?
C72 H72B 0.9700 . ?
O66 C73 1.209(13) . ?
C73 C74 1.489(15) . ?
C74 C75 1.371(14) . ?
C74 C83 1.422(15) . ?
C75 C76 1.416(15) . ?
C75 H75 0.9300 . ?
C76 C77 1.428(15) . ?
C76 C81 1.428(15) . ?
C77 C78 1.375(17) . ?
C77 H77 0.9300 . ?
C78 C79 1.381(18) . ?
C78 H78 0.9300 . ?
C79 C80 1.366(17) . ?
C79 H79 0.9300 . ?
C80 C81 1.412(16) . ?
C80 H80 0.9300 . ?
C81 C82 1.394(15) . ?
C82 C83 1.375(14) . ?
C82 H82 0.9300 . ?
C83 H83 0.9300 . ?
O91 C91 1.224(14) . ?
C91 C96 1.471(16) . ?
C91 C92 1.474(17) . ?
C92 C93 1.321(16) . ?
C92 H92 0.9300 . ?
C93 C94 1.442(16) . ?
C93 H93 0.9300 . ?
O92 C94 1.428(12) . ?
O92 H92O 0.86(11) . ?
C94 C95 1.563(14) . ?
C94 H94 0.9800 . ?
C95 C97 1.494(16) . ?
C95 C96 1.533(14) . ?
C95 C100 1.557(17) . ?
C96 C102 1.558(14) . ?
C96 H96 0.9800 . ?
O93 C97 1.208(14) . ?
O94 C97 1.308(13) . ?
O94 C98 1.471(14) . ?
C98 C99 1.40(2) . ?
C98 H98A 0.9700 . ?
C98 H98B 0.9700 . ?
C99 H99A 0.9600 . ?
C99 H99B 0.9600 . ?
C99 H99C 0.9600 . ?
O95 C100 1.221(15) . ?
C100 C101 1.48(2) . ?
C101 H10B 0.9600 . ?
C101 H10A 0.9600 . ?
C101 H10C 0.9600 . ?
C102 C103 1.513(14) . ?
C102 H10E 0.9700 . ?
C102 H10D 0.9700 . ?
O96 C103 1.213(12) . ?
C103 C104 1.480(14) . ?
C104 C105 1.377(14) . ?
C104 C113 1.392(14) . ?
C105 C106 1.421(15) . ?
C105 H105 0.9300 . ?
C106 C107 1.389(13) . ?
C106 C111 1.449(15) . ?
C107 C108 1.354(15) . ?
C107 H107 0.9300 . ?
C108 C109 1.392(17) . ?
C108 H108 0.9300 . ?
C109 C110 1.383(15) . ?
C109 H109 0.9300 . ?
C110 C111 1.412(15) . ?
C110 H110 0.9300 . ?
C111 C112 1.417(14) . ?
C112 C113 1.320(15) . ?
C112 H112 0.9300 . ?
C113 H113 0.9300 . ?

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
O1 C1 C2 122.6(12) . . ?
O1 C1 C6 119.8(11) . . ?
C2 C1 C6 117.5(10) . . ?
C3 C2 C1 121.5(11) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 123.1(11) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C4 O2 H2O 109.5 . . ?
O2 C4 C3 112.3(9) . . ?
O2 C4 C5 115.3(8) . . ?
C3 C4 C5 109.8(8) . . ?
O2 C4 H4 106.3 . . ?
C3 C4 H4 106.3 . . ?
C5 C4 H4 106.3 . . ?
C7 C5 C4 111.6(8) . . ?
C7 C5 C10 109.3(8) . . ?
C4 C5 C10 110.7(8) . . ?
C7 C5 C6 110.1(8) . . ?
C4 C5 C6 106.0(7) . . ?
C10 C5 C6 109.0(8) . . ?
C1 C6 C12 110.0(9) . . ?
C1 C6 C5 109.2(9) . . ?
C12 C6 C5 115.3(8) . . ?
C1 C6 H6 107.3 . . ?
C12 C6 H6 107.3 . . ?
C5 C6 H6 107.3 . . ?
C7 O4 C8 114.3(8) . . ?
O3 C7 O4 124.5(10) . . ?
O3 C7 C5 124.8(10) . . ?
O4 C7 C5 110.7(9) . . ?
O4 C8 C9 107.0(9) . . ?
O4 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
O4 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O5 C10 C11 121.2(11) . . ?
O5 C10 C5 119.6(10) . . ?
C11 C10 C5 119.1(11) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C6 112.5(8) . . ?
C13 C12 H12A 109.1 . . ?
C6 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C6 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
O6 C13 C14 120.1(11) . . ?
O6 C13 C12 121.2(10) . . ?
C14 C13 C12 118.8(9) . . ?
C15 C14 C23 118.6(9) . . ?
C15 C14 C13 121.9(10) . . ?
C23 C14 C13 119.5(9) . . ?
C14 C15 C16 121.8(10) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C17 122.9(11) . . ?
C15 C16 C21 118.2(10) . . ?
C17 C16 C21 118.9(10) . . ?
C18 C17 C16 121.0(13) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 121.1(13) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 120.0(13) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.8(13) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C22 C21 C20 125.3(11) . . ?
C22 C21 C16 116.6(10) . . ?
C20 C21 C16 118.1(11) . . ?
C23 C22 C21 124.6(10) . . ?
C23 C22 H22 117.7 . . ?
C21 C22 H22 117.7 . . ?
C22 C23 C14 120.2(10) . . ?
C22 C23 H23 119.9 . . ?
C14 C23 H23 119.9 . . ?
O31 C31 C32 124.0(14) . . ?
O31 C31 C36 119.2(12) . . ?
C32 C31 C36 116.8(11) . . ?
C33 C32 C31 123.6(13) . . ?
C33 C32 H32 118.2 . . ?
C31 C32 H32 118.2 . . ?
C32 C33 C34 120.5(13) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C34 O32 H32O 109.5 . . ?
O32 C34 C33 112.9(10) . . ?
O32 C34 C35 113.0(9) . . ?
C33 C34 C35 109.8(10) . . ?
O32 C34 H34 106.9 . . ?
C33 C34 H34 106.9 . . ?
C35 C34 H34 106.9 . . ?
C36 C35 C37 110.2(9) . . ?
C36 C35 C40 110.2(10) . . ?
C37 C35 C40 105.8(11) . . ?
C36 C35 C34 107.0(8) . . ?
C37 C35 C34 112.5(9) . . ?
C40 C35 C34 111.2(11) . . ?
C42 C36 C35 118.0(9) . . ?
C42 C36 C31 111.3(9) . . ?
C35 C36 C31 107.7(10) . . ?
C42 C36 H36 106.4 . . ?
C35 C36 H36 106.4 . . ?
C31 C36 H36 106.4 . . ?
C37 O34 C38 117.9(9) . . ?
O33 C37 O34 123.7(10) . . ?
O33 C37 C35 124.0(10) . . ?
O34 C37 C35 112.3(9) . . ?
O34 C38 C39 109.3(10) . . ?
O34 C38 H38A 109.8 . . ?
C39 C38 H38A 109.8 . . ?
O34 C38 H38B 109.8 . . ?
C39 C38 H38B 109.8 . . ?
H38A C38 H38B 108.3 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O35 C40 C35 122.0(15) . . ?
O35 C40 C41 117.6(16) . . ?
C35 C40 C41 120.4(17) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C43 C42 C36 114.0(9) . . ?
C43 C42 H42A 108.7 . . ?
C36 C42 H42A 108.7 . . ?
C43 C42 H42B 108.7 . . ?
C36 C42 H42B 108.7 . . ?
H42A C42 H42B 107.6 . . ?
O36 C43 C44 120.0(11) . . ?
O36 C43 C42 119.0(11) . . ?
C44 C43 C42 121.0(10) . . ?
C45 C44 C53 119.4(10) . . ?
C45 C44 C43 121.7(10) . . ?
C53 C44 C43 118.9(9) . . ?
C44 C45 C46 120.9(10) . . ?
C44 C45 H45 119.5 . . ?
C46 C45 H45 119.5 . . ?
C47 C46 C45 122.1(11) . . ?
C47 C46 C51 120.0(11) . . ?
C45 C46 C51 117.8(10) . . ?
C48 C47 C46 121.2(11) . . ?
C48 C47 H47 119.4 . . ?
C46 C47 H47 119.4 . . ?
C47 C48 C49 119.9(11) . . ?
C47 C48 H48 120.1 . . ?
C49 C48 H48 120.1 . . ?
C50 C49 C48 120.2(11) . . ?
C50 C49 H49 119.9 . . ?
C48 C49 H49 119.9 . . ?
C49 C50 C51 120.1(11) . . ?
C49 C50 H50 119.9 . . ?
C51 C50 H50 119.9 . . ?
C52 C51 C46 121.0(10) . . ?
C52 C51 C50 120.6(10) . . ?
C46 C51 C50 118.4(10) . . ?
C53 C52 C51 120.2(10) . . ?
C53 C52 H52 119.9 . . ?
C51 C52 H52 119.9 . . ?
C52 C53 C44 120.5(10) . . ?
C52 C53 H53 119.8 . . ?
C44 C53 H53 119.8 . . ?
O61 C61 C62 122.2(13) . . ?
O61 C61 C66 122.5(11) . . ?
C62 C61 C66 115.3(11) . . ?
C63 C62 C61 121.8(13) . . ?
C63 C62 H62 119.1 . . ?
C61 C62 H62 119.1 . . ?
C62 C63 C64 123.5(12) . . ?
C62 C63 H63 118.2 . . ?
C64 C63 H63 118.2 . . ?
C64 O62 H62O 109.5 . . ?
O62 C64 C63 113.6(10) . . ?
O62 C64 C65 114.3(9) . . ?
C63 C64 C65 109.3(10) . . ?
O62 C64 H64 106.3 . . ?
C63 C64 H64 106.3 . . ?
C65 C64 H64 106.3 . . ?
C66 C65 C70 110.8(8) . . ?
C66 C65 C67 110.5(9) . . ?
C70 C65 C67 109.7(8) . . ?
C66 C65 C64 107.0(8) . . ?
C70 C65 C64 107.6(8) . . ?
C67 C65 C64 111.2(8) . . ?
C65 C66 C61 110.8(9) . . ?
C65 C66 C72 115.5(8) . . ?
C61 C66 C72 108.7(9) . . ?
C65 C66 H66 107.1 . . ?
C61 C66 H66 107.1 . . ?
C72 C66 H66 107.1 . . ?
C67 O64 C68 115.5(11) . . ?
O63 C67 O64 124.2(10) . . ?
O63 C67 C65 124.6(10) . . ?
O64 C67 C65 111.2(10) . . ?
C69 C68 O64 111.3(13) . . ?
C69 C68 H68 124.3 . . ?
O64 C68 H68 124.3 . . ?
C68 C69 H69A 120.0 . . ?
C68 C69 H69B 120.0 . . ?
H69A C69 H69B 120.0 . . ?
O65 C70 C71 120.5(11) . . ?
O65 C70 C65 119.5(10) . . ?
C71 C70 C65 120.0(10) . . ?
C70 C71 H71A 109.5 . . ?
C70 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
C70 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C73 C72 C66 114.0(8) . . ?
C73 C72 H72A 108.7 . . ?
C66 C72 H72A 108.7 . . ?
C73 C72 H72B 108.7 . . ?
C66 C72 H72B 108.7 . . ?
H72A C72 H72B 107.6 . . ?
O66 C73 C72 121.1(10) . . ?
O66 C73 C74 120.2(10) . . ?
C72 C73 C74 118.7(9) . . ?
C75 C74 C83 118.8(9) . . ?
C75 C74 C73 122.8(10) . . ?
C83 C74 C73 118.4(9) . . ?
C74 C75 C76 121.6(10) . . ?
C74 C75 H75 119.2 . . ?
C76 C75 H75 119.2 . . ?
C75 C76 C77 122.2(10) . . ?
C75 C76 C81 118.8(9) . . ?
C77 C76 C81 119.0(10) . . ?
C78 C77 C76 119.7(11) . . ?
C78 C77 H77 120.2 . . ?
C76 C77 H77 120.2 . . ?
C77 C78 C79 120.7(11) . . ?
C77 C78 H78 119.6 . . ?
C79 C78 H78 119.6 . . ?
C80 C79 C78 121.5(11) . . ?
C80 C79 H79 119.2 . . ?
C78 C79 H79 119.2 . . ?
C79 C80 C81 120.3(12) . . ?
C79 C80 H80 119.8 . . ?
C81 C80 H80 119.8 . . ?
C82 C81 C80 122.3(11) . . ?
C82 C81 C76 119.0(10) . . ?
C80 C81 C76 118.7(10) . . ?
C83 C82 C81 121.0(10) . . ?
C83 C82 H82 119.5 . . ?
C81 C82 H82 119.5 . . ?
C82 C83 C74 120.8(9) . . ?
C82 C83 H83 119.6 . . ?
C74 C83 H83 119.6 . . ?
O91 C91 C96 122.5(12) . . ?
O91 C91 C92 119.5(12) . . ?
C96 C91 C92 117.8(10) . . ?
C93 C92 C91 118.9(11) . . ?
C93 C92 H92 120.6 . . ?
C91 C92 H92 120.6 . . ?
C92 C93 C94 124.8(11) . . ?
C92 C93 H93 117.6 . . ?
C94 C93 H93 117.6 . . ?
C94 O92 H92O 94(7) . . ?
O92 C94 C93 113.1(9) . . ?
O92 C94 C95 112.8(8) . . ?
C93 C94 C95 107.9(9) . . ?
O92 C94 H94 107.6 . . ?
C93 C94 H94 107.6 . . ?
C95 C94 H94 107.6 . . ?
C97 C95 C96 111.3(10) . . ?
C97 C95 C100 110.3(9) . . ?
C96 C95 C100 108.2(9) . . ?
C97 C95 C94 111.7(9) . . ?
C96 C95 C94 104.9(7) . . ?
C100 C95 C94 110.4(10) . . ?
C91 C96 C95 110.0(9) . . ?
C91 C96 C102 109.9(9) . . ?
C95 C96 C102 116.1(7) . . ?
C91 C96 H96 106.8 . . ?
C95 C96 H96 106.8 . . ?
C102 C96 H96 106.8 . . ?
C97 O94 C98 116.0(11) . . ?
O93 C97 O94 123.3(12) . . ?
O93 C97 C95 123.0(10) . . ?
O94 C97 C95 113.6(11) . . ?
C99 C98 O94 109.0(13) . . ?
C99 C98 H98A 109.9 . . ?
O94 C98 H98A 109.9 . . ?
C99 C98 H98B 109.9 . . ?
O94 C98 H98B 109.9 . . ?
H98A C98 H98B 108.3 . . ?
C98 C99 H99A 109.5 . . ?
C98 C99 H99B 109.5 . . ?
H99A C99 H99B 109.5 . . ?
C98 C99 H99C 109.5 . . ?
H99A C99 H99C 109.5 . . ?
H99B C99 H99C 109.5 . . ?
O95 C100 C101 122.9(14) . . ?
O95 C100 C95 118.3(12) . . ?
C101 C100 C95 118.8(12) . . ?
C100 C101 H10B 109.5 . . ?
C100 C101 H10A 109.5 . . ?
H10B C101 H10A 109.5 . . ?
C100 C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
C103 C102 C96 111.9(8) . . ?
C103 C102 H10E 109.2 . . ?
C96 C102 H10E 109.2 . . ?
C103 C102 H10D 109.2 . . ?
C96 C102 H10D 109.2 . . ?
H10E C102 H10D 107.9 . . ?
O96 C103 C104 121.0(10) . . ?
O96 C103 C102 120.7(9) . . ?
C104 C103 C102 118.4(8) . . ?
C105 C104 C113 120.6(10) . . ?
C105 C104 C103 121.6(9) . . ?
C113 C104 C103 117.7(9) . . ?
C104 C105 C106 120.2(10) . . ?
C104 C105 H105 119.9 . . ?
C106 C105 H105 119.9 . . ?
C107 C106 C105 123.3(10) . . ?
C107 C106 C111 118.8(9) . . ?
C105 C106 C111 117.9(9) . . ?
C108 C107 C106 120.9(11) . . ?
C108 C107 H107 119.6 . . ?
C106 C107 H107 119.6 . . ?
C107 C108 C109 121.4(11) . . ?
C107 C108 H108 119.3 . . ?
C109 C108 H108 119.3 . . ?
C110 C109 C108 120.4(11) . . ?
C110 C109 H109 119.8 . . ?
C108 C109 H109 119.8 . . ?
C109 C110 C111 119.6(11) . . ?
C109 C110 H110 120.2 . . ?
C111 C110 H110 120.2 . . ?
C110 C111 C112 123.3(10) . . ?
C110 C111 C106 118.8(10) . . ?
C112 C111 C106 117.9(9) . . ?
C113 C112 C111 122.1(10) . . ?
C113 C112 H112 119.0 . . ?
C111 C112 H112 119.0 . . ?
C112 C113 C104 121.2(10) . . ?
C112 C113 H113 119.4 . . ?
C104 C113 H113 119.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2O O4 0.82 2.24 2.742(10) 119.7 . yes
O2 H2O O32 0.82 2.54 3.208(13) 139.6 . yes
O32 H32O O34 0.82 2.15 2.683(11) 122.3 . yes
O62 H62O O64 0.82 2.07 2.658(11) 128.3 . yes
O92 H92O O62 0.86(11) 2.50(11) 3.134(14) 130(9) . yes
O92 H92O O94 0.86(11) 2.07(11) 2.751(12) 135(9) . yes

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.072






















_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_O20_003_P2(1)n
_database_code_depnum_ccdc_archive 'CCDC 2076254'
loop_
_audit_author_name
_audit_author_address
'Myoung Soo Lah'
;Ulsan National Institute of Science and Technology (UNIST)
South Korea
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'Ethyl (2R,3aR,4S,5S)-4-acetyl-2-(4-nitrophenyl)-6-oxohexahydro-2,5-methanobenzo[d][1,3]dioxole-4-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 N O8'
_chemical_formula_weight         389.35

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

_space_group_crystal_system      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                   7.9677(16)
_cell_length_b                   8.9993(18)
_cell_length_c                   24.879(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.37(3)
_cell_angle_gamma                90
_cell_volume                     1764.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    13187
_cell_measurement_theta_min      2.265
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.515
_exptl_crystal_size_min          0.343
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6946
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16531
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.410
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4049
_reflns_number_gt                3180
_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       'Rigaku Rapid Auto'
_computing_cell_refinement       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0445P)²+1.2447P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4049
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7733(3) 0.4072(2) 0.31384(9) 0.0312(5) Uani 1 1 d . . . . .
O1 O 0.9029(2) 0.3427(2) 0.30918(7) 0.0488(5) Uani 1 1 d . . . . .
C2 C 0.6696(3) 0.4916(3) 0.26782(9) 0.0337(5) Uani 1 1 d . . . . .
H21 H 0.594(3) 0.418(3) 0.2461(10) 0.038(7) Uiso 1 1 d . . . . .
H22 H 0.743(3) 0.529(3) 0.2441(10) 0.037(7) Uiso 1 1 d . . . . .
O2 O 0.69466(19) 0.71388(16) 0.32177(5) 0.0294(3) Uani 1 1 d . . . . .
C3 C 0.5724(3) 0.6161(2) 0.29040(9) 0.0294(5) Uani 1 1 d . . . . .
H3 H 0.509(3) 0.675(3) 0.2613(10) 0.038(7) Uiso 1 1 d . . . . .
O3 O 0.49602(17) 0.67185(15) 0.37534(6) 0.0257(3) Uani 1 1 d . . . . .
C4 C 0.4578(3) 0.5659(2) 0.33230(8) 0.0254(4) Uani 1 1 d . . . . .
H4 H 0.335(3) 0.572(2) 0.3182(9) 0.027(6) Uiso 1 1 d . . . . .
C5 C 0.6746(3) 0.6925(2) 0.37718(8) 0.0246(4) Uani 1 1 d . . . . .
C6 C 0.7679(3) 0.5526(2) 0.39997(8) 0.0253(4) Uani 1 1 d . . . . .
H61 H 0.751(3) 0.540(2) 0.4379(8) 0.016(5) Uiso 1 1 d . . . . .
H62 H 0.887(3) 0.565(2) 0.3997(8) 0.022(5) Uiso 1 1 d . . . . .
C7 C 0.7034(3) 0.4110(2) 0.36753(8) 0.0256(4) Uani 1 1 d . . . . .
H7 H 0.743(3) 0.324(2) 0.3880(8) 0.018(5) Uiso 1 1 d . . . . .
C8 C 0.5080(3) 0.4123(2) 0.35666(8) 0.0241(4) Uani 1 1 d . . . . .
O4 O 0.3165(2) 0.30635(17) 0.28227(6) 0.0378(4) Uani 1 1 d . . . . .
O5 O 0.4990(2) 0.15788(16) 0.33442(6) 0.0354(4) Uani 1 1 d . . . . .
C9 C 0.4303(3) 0.2880(2) 0.31919(8) 0.0260(4) Uani 1 1 d . . . . .
C10 C 0.4145(3) 0.0258(2) 0.30848(10) 0.0341(5) Uani 1 1 d . . . . .
H101 H 0.381(3) 0.046(3) 0.2705(10) 0.031(6) Uiso 1 1 d . . . . .
H102 H 0.503(3) -0.049(3) 0.3155(10) 0.039(7) Uiso 1 1 d . . . . .
C11 C 0.2660(4) -0.0152(3) 0.33574(11) 0.0437(6) Uani 1 1 d . . . . .
H111 H 0.182(3) 0.064(3) 0.3326(10) 0.043(7) Uiso 1 1 d . . . . .
H112 H 0.221(3) -0.108(3) 0.3196(11) 0.049(8) Uiso 1 1 d . . . . .
H113 H 0.303(4) -0.031(3) 0.3754(14) 0.066(9) Uiso 1 1 d . . . . .
O6 O 0.5239(2) 0.3406(2) 0.45017(6) 0.0437(4) Uani 1 1 d . . . . .
C12 C 0.4339(3) 0.3879(2) 0.41077(9) 0.0292(5) Uani 1 1 d . . . . .
C13 C 0.2508(3) 0.4221(3) 0.41050(12) 0.0397(6) Uani 1 1 d . . . . .
H131 H 0.238(4) 0.530(4) 0.4136(12) 0.062(9) Uiso 1 1 d . . . . .
H132 H 0.189(4) 0.378(3) 0.3777(13) 0.058(9) Uiso 1 1 d . . . . .
H133 H 0.213(4) 0.376(4) 0.4408(14) 0.073(10) Uiso 1 1 d . . . . .
C14 C 0.7256(2) 0.8295(2) 0.41001(8) 0.0242(4) Uani 1 1 d . . . . .
C15 C 0.8373(3) 0.9326(2) 0.39364(9) 0.0279(4) Uani 1 1 d . . . . .
H15 H 0.881(3) 0.916(2) 0.3626(9) 0.024(6) Uiso 1 1 d . . . . .
C16 C 0.8833(3) 1.0581(2) 0.42443(8) 0.0269(4) Uani 1 1 d . . . . .
H16 H 0.961(3) 1.129(3) 0.4139(10) 0.034(6) Uiso 1 1 d . . . . .
O1N O 0.9521(2) 1.30407(18) 0.48805(7) 0.0408(4) Uani 1 1 d . . . . .
O2N O 0.8096(2) 1.22067(19) 0.54904(7) 0.0422(4) Uani 1 1 d . . . . .
N1 N 0.8625(2) 1.21025(19) 0.50541(8) 0.0304(4) Uani 1 1 d . . . . .
C17 C 0.8152(3) 1.0777(2) 0.47208(8) 0.0256(4) Uani 1 1 d . . . . .
C18 C 0.7066(3) 0.9757(2) 0.48980(9) 0.0291(5) Uani 1 1 d . . . . .
H18 H 0.667(3) 0.993(3) 0.5224(10) 0.037(6) Uiso 1 1 d . . . . .
C19 C 0.6611(3) 0.8515(2) 0.45862(9) 0.0292(5) Uani 1 1 d . . . . .
H19 H 0.586(3) 0.778(3) 0.4694(10) 0.041(7) 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
C1 O1 1.205(3) . ?
C1 C2 1.515(3) . ?
C1 C7 1.521(3) . ?
C2 C3 1.516(3) . ?
C2 H21 1.00(3) . ?
C2 H22 0.95(3) . ?
O2 C5 1.424(2) . ?
O2 C3 1.453(3) . ?
C3 C4 1.550(3) . ?
C3 H3 0.98(3) . ?
O3 C5 1.429(2) . ?
O3 C4 1.433(2) . ?
C4 C8 1.539(3) . ?
C4 H4 0.99(2) . ?
C5 C14 1.502(3) . ?
C5 C6 1.529(3) . ?
C6 C7 1.555(3) . ?
C6 H61 0.98(2) . ?
C6 H62 0.95(2) . ?
C7 C8 1.541(3) . ?
C7 H7 0.96(2) . ?
C8 C9 1.528(3) . ?
C8 C12 1.562(3) . ?
O4 C9 1.205(3) . ?
O5 C9 1.324(2) . ?
O5 C10 1.468(3) . ?
C10 C11 1.493(4) . ?
C10 H101 0.96(2) . ?
C10 H102 0.97(3) . ?
C11 H111 0.97(3) . ?
C11 H112 0.97(3) . ?
C11 H113 1.00(3) . ?
O6 C12 1.205(3) . ?
C12 C13 1.490(3) . ?
C13 H131 0.98(3) . ?
C13 H132 0.97(3) . ?
C13 H133 0.95(3) . ?
C14 C15 1.387(3) . ?
C14 C19 1.395(3) . ?
C15 C16 1.384(3) . ?
C15 H15 0.91(2) . ?
C16 C17 1.385(3) . ?
C16 H16 0.95(3) . ?
O1N N1 1.225(2) . ?
O2N N1 1.224(2) . ?
N1 C17 1.470(3) . ?
C17 C18 1.377(3) . ?
C18 C19 1.379(3) . ?
C18 H18 0.92(3) . ?
C19 H19 0.96(3) . ?

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
O1 C1 C2 123.3(2) . . ?
O1 C1 C7 121.6(2) . . ?
C2 C1 C7 115.07(18) . . ?
C1 C2 C3 110.01(17) . . ?
C1 C2 H21 107.2(14) . . ?
C3 C2 H21 112.9(15) . . ?
C1 C2 H22 109.4(15) . . ?
C3 C2 H22 111.0(15) . . ?
H21 C2 H22 106(2) . . ?
C5 O2 C3 106.10(15) . . ?
O2 C3 C2 107.96(19) . . ?
O2 C3 C4 103.27(15) . . ?
C2 C3 C4 114.63(18) . . ?
O2 C3 H3 107.5(14) . . ?
C2 C3 H3 111.3(14) . . ?
C4 C3 H3 111.5(14) . . ?
C5 O3 C4 102.27(15) . . ?
O3 C4 C8 106.78(15) . . ?
O3 C4 C3 103.13(16) . . ?
C8 C4 C3 112.44(17) . . ?
O3 C4 H4 108.5(13) . . ?
C8 C4 H4 112.1(13) . . ?
C3 C4 H4 113.3(13) . . ?
O2 C5 O3 103.79(15) . . ?
O2 C5 C14 110.86(16) . . ?
O3 C5 C14 108.27(16) . . ?
O2 C5 C6 110.70(16) . . ?
O3 C5 C6 109.43(16) . . ?
C14 C5 C6 113.33(16) . . ?
C5 C6 C7 112.11(17) . . ?
C5 C6 H61 108.8(12) . . ?
C7 C6 H61 109.0(12) . . ?
C5 C6 H62 109.5(13) . . ?
C7 C6 H62 110.0(13) . . ?
H61 C6 H62 107.3(17) . . ?
C1 C7 C8 109.63(17) . . ?
C1 C7 C6 109.79(17) . . ?
C8 C7 C6 109.48(16) . . ?
C1 C7 H7 108.0(12) . . ?
C8 C7 H7 110.3(12) . . ?
C6 C7 H7 109.6(12) . . ?
C9 C8 C4 111.01(16) . . ?
C9 C8 C7 114.22(16) . . ?
C4 C8 C7 105.92(16) . . ?
C9 C8 C12 104.61(16) . . ?
C4 C8 C12 110.89(16) . . ?
C7 C8 C12 110.28(17) . . ?
C9 O5 C10 116.50(17) . . ?
O4 C9 O5 124.97(19) . . ?
O4 C9 C8 123.90(19) . . ?
O5 C9 C8 111.05(17) . . ?
O5 C10 C11 110.1(2) . . ?
O5 C10 H101 108.8(14) . . ?
C11 C10 H101 111.5(14) . . ?
O5 C10 H102 102.1(15) . . ?
C11 C10 H102 110.3(15) . . ?
H101 C10 H102 114(2) . . ?
C10 C11 H111 111.4(16) . . ?
C10 C11 H112 107.0(16) . . ?
H111 C11 H112 113(2) . . ?
C10 C11 H113 110.0(18) . . ?
H111 C11 H113 107(2) . . ?
H112 C11 H113 109(2) . . ?
O6 C12 C13 122.9(2) . . ?
O6 C12 C8 119.7(2) . . ?
C13 C12 C8 117.36(19) . . ?
C12 C13 H131 108.5(18) . . ?
C12 C13 H132 107.3(18) . . ?
H131 C13 H132 115(3) . . ?
C12 C13 H133 109(2) . . ?
H131 C13 H133 109(3) . . ?
H132 C13 H133 108(3) . . ?
C15 C14 C19 119.52(19) . . ?
C15 C14 C5 121.58(18) . . ?
C19 C14 C5 118.89(18) . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 120.5(14) . . ?
C14 C15 H15 118.7(14) . . ?
C15 C16 C17 118.2(2) . . ?
C15 C16 H16 121.7(15) . . ?
C17 C16 H16 120.1(15) . . ?
O2N N1 O1N 123.64(19) . . ?
O2N N1 C17 117.99(18) . . ?
O1N N1 C17 118.37(18) . . ?
C18 C17 C16 122.13(19) . . ?
C18 C17 N1 118.79(19) . . ?
C16 C17 N1 119.07(19) . . ?
C17 C18 C19 119.1(2) . . ?
C17 C18 H18 118.8(16) . . ?
C19 C18 H18 122.1(16) . . ?
C18 C19 C14 120.2(2) . . ?
C18 C19 H19 121.9(15) . . ?
C14 C19 H19 117.9(15) . . ?

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.050










































_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
