# 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_zz
_audit_block_doi                 10.5517/ccdc.csd.cc2dd858
_database_code_depnum_ccdc_archive 'CCDC 2216319'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1038/s41467-023-38154-9 2023
loop_
_audit_author_name
_audit_author_address
'Cheng-Yu Zheng'
;simm
China
;
_audit_update_record             
;
2022-11-23 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_audit_creation_date             2022-11-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H20 O4'
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   10.2733(2)
_cell_length_b                   10.3627(2)
_cell_length_c                   13.3957(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1426.09(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9274
_cell_measurement_temperature    170
_cell_measurement_theta_max      74.722
_cell_measurement_theta_min      5.397
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1177 before and 0.0652 after correction. The Ratio of minimum to maximum transmission is 0.8993. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14626
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.719
_diffrn_reflns_theta_min         5.397
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2791
_reflns_number_total             2912
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1137 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2912
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      1.066
_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)+(0.0481P)²+0.1788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0869
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C1(H1), C2(H2A)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O2 O 0.91711(13) 0.54135(14) 0.77283(11) 0.0313(3) Uani 1 1 d . . . . .
H2 H 0.857489 0.595232 0.783051 0.047 Uiso 1 1 calc R U . . .
O4 O 0.83051(15) 0.69873(14) 0.58314(12) 0.0348(3) Uani 1 1 d . . . . .
O1 O 0.28433(15) 0.21921(16) 0.67181(13) 0.0390(4) Uani 1 1 d . . . . .
O3 O 1.04779(16) 0.69194(17) 0.56827(13) 0.0444(4) Uani 1 1 d . . . . .
C7 C 0.82351(17) 0.43623(18) 0.62730(14) 0.0239(4) Uani 1 1 d . . . . .
C12 C 0.9444(2) 0.6378(2) 0.57165(14) 0.0286(4) Uani 1 1 d . . . . .
C11 C 0.92420(19) 0.49346(19) 0.55731(14) 0.0277(4) Uani 1 1 d . . . . .
H11 H 0.890891 0.480957 0.487839 0.033 Uiso 1 1 calc R U . . .
C4 C 0.48623(18) 0.31426(18) 0.63150(15) 0.0240(4) Uani 1 1 d . . . . .
C6 C 0.70866(18) 0.39327(18) 0.59320(14) 0.0227(4) Uani 1 1 d . . . . .
H6 H 0.687954 0.407406 0.524949 0.027 Uiso 1 1 calc R U . . .
C5 C 0.61379(18) 0.32592(17) 0.65541(14) 0.0227(4) Uani 1 1 d . . . . .
C8 C 0.86195(18) 0.42378(18) 0.73598(14) 0.0255(4) Uani 1 1 d . . . . .
H8 H 0.931473 0.356410 0.739739 0.031 Uiso 1 1 calc R U . . .
C9 C 0.74967(19) 0.37779(19) 0.80085(14) 0.0265(4) Uani 1 1 d . . . . .
H9A H 0.691252 0.451465 0.815212 0.032 Uiso 1 1 calc R U . . .
H9B H 0.784393 0.345800 0.865200 0.032 Uiso 1 1 calc R U . . .
C1 C 0.5703(2) 0.21877(19) 0.82007(15) 0.0321(4) Uani 1 1 d . . . . .
H1 H 0.596558 0.197271 0.886012 0.038 Uiso 1 1 calc R U . . .
C10 C 0.67075(19) 0.26918(18) 0.74996(14) 0.0256(4) Uani 1 1 d . . . . .
C3 C 0.39719(19) 0.24221(18) 0.69753(16) 0.0288(4) Uani 1 1 d . . . . .
C15 C 0.42354(19) 0.3740(2) 0.54136(15) 0.0299(4) Uani 1 1 d . . . . .
H15A H 0.372520 0.449420 0.561812 0.045 Uiso 1 1 calc R U . . .
H15B H 0.366122 0.310772 0.509426 0.045 Uiso 1 1 calc R U . . .
H15C H 0.491070 0.400827 0.494040 0.045 Uiso 1 1 calc R U . . .
C2 C 0.4459(2) 0.2021(2) 0.79552(17) 0.0358(5) Uani 1 1 d . . . . .
H2A H 0.387897 0.163814 0.842141 0.043 Uiso 1 1 calc R U . . .
C13 C 1.0556(2) 0.4242(2) 0.56349(18) 0.0381(5) Uani 1 1 d . . . . .
H13A H 1.095760 0.441449 0.628509 0.057 Uiso 1 1 calc R U . . .
H13B H 1.112868 0.455760 0.510282 0.057 Uiso 1 1 calc R U . . .
H13C H 1.042432 0.331105 0.555617 0.057 Uiso 1 1 calc R U . . .
C14 C 0.7588(2) 0.15222(19) 0.72423(17) 0.0331(5) Uani 1 1 d . . . . .
H14A H 0.705855 0.083596 0.694503 0.050 Uiso 1 1 calc R U . . .
H14B H 0.800225 0.120073 0.785267 0.050 Uiso 1 1 calc R U . . .
H14C H 0.826037 0.179106 0.676663 0.050 Uiso 1 1 calc R U . . .
C16 C 0.8352(3) 0.8359(2) 0.6013(2) 0.0446(6) Uani 1 1 d . . . . .
H16A H 0.912882 0.872352 0.569518 0.067 Uiso 1 1 calc R U . . .
H16B H 0.838638 0.851898 0.673344 0.067 Uiso 1 1 calc R U . . .
H16C H 0.757247 0.876733 0.573310 0.067 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
O2 H2 0.8400 . ?
O2 C8 1.431(2) . ?
O4 C12 1.338(3) . ?
O4 C16 1.443(3) . ?
O1 C3 1.233(3) . ?
O3 C12 1.203(3) . ?
C7 C11 1.517(3) . ?
C7 C6 1.341(3) . ?
C7 C8 1.514(3) . ?
C12 C11 1.522(3) . ?
C11 H11 1.0000 . ?
C11 C13 1.532(3) . ?
C4 C5 1.354(3) . ?
C4 C3 1.475(3) . ?
C4 C15 1.502(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.460(3) . ?
C5 C10 1.514(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.521(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.546(3) . ?
C1 H1 0.9500 . ?
C1 C10 1.490(3) . ?
C1 C2 1.331(3) . ?
C10 C14 1.551(3) . ?
C3 C2 1.465(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C2 H2A 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C8 O2 H2 109.5 . . ?
C12 O4 C16 117.08(18) . . ?
C6 C7 C11 121.28(17) . . ?
C6 C7 C8 121.92(17) . . ?
C8 C7 C11 116.73(16) . . ?
O4 C12 C11 111.06(17) . . ?
O3 C12 O4 123.81(19) . . ?
O3 C12 C11 125.0(2) . . ?
C7 C11 C12 113.52(16) . . ?
C7 C11 H11 106.9 . . ?
C7 C11 C13 112.63(17) . . ?
C12 C11 H11 106.9 . . ?
C12 C11 C13 109.49(17) . . ?
C13 C11 H11 106.9 . . ?
C5 C4 C3 120.21(18) . . ?
C5 C4 C15 124.63(18) . . ?
C3 C4 C15 115.14(17) . . ?
C7 C6 H6 118.3 . . ?
C7 C6 C5 123.47(17) . . ?
C5 C6 H6 118.3 . . ?
C4 C5 C6 123.61(17) . . ?
C4 C5 C10 122.49(17) . . ?
C6 C5 C10 113.90(16) . . ?
O2 C8 C7 111.24(16) . . ?
O2 C8 H8 107.1 . . ?
O2 C8 C9 111.71(16) . . ?
C7 C8 H8 107.1 . . ?
C7 C8 C9 112.23(15) . . ?
C9 C8 H8 107.1 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C8 C9 C10 111.97(15) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C10 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C2 C1 C10 123.69(19) . . ?
C5 C10 C9 106.80(14) . . ?
C5 C10 C14 110.06(15) . . ?
C9 C10 C14 111.16(16) . . ?
C1 C10 C5 113.32(16) . . ?
C1 C10 C9 109.91(16) . . ?
C1 C10 C14 105.67(16) . . ?
O1 C3 C4 120.89(19) . . ?
O1 C3 C2 121.11(19) . . ?
C2 C3 C4 117.97(18) . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C2 C3 120.84(19) . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 H2A 119.6 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O2 C8 C9 C10 167.48(14) . . . . ?
O4 C12 C11 C7 -43.0(2) . . . . ?
O4 C12 C11 C13 -169.78(17) . . . . ?
O1 C3 C2 C1 175.0(2) . . . . ?
O3 C12 C11 C7 140.5(2) . . . . ?
O3 C12 C11 C13 13.7(3) . . . . ?
C7 C6 C5 C4 160.78(18) . . . . ?
C7 C6 C5 C10 -19.4(3) . . . . ?
C7 C8 C9 C10 41.8(2) . . . . ?
C11 C7 C6 C5 173.72(17) . . . . ?
C11 C7 C8 O2 48.4(2) . . . . ?
C11 C7 C8 C9 174.40(16) . . . . ?
C4 C5 C10 C9 -130.24(18) . . . . ?
C4 C5 C10 C1 -9.1(2) . . . . ?
C4 C5 C10 C14 109.0(2) . . . . ?
C4 C3 C2 C1 -6.7(3) . . . . ?
C6 C7 C11 C12 111.1(2) . . . . ?
C6 C7 C11 C13 -123.79(19) . . . . ?
C6 C7 C8 O2 -134.71(18) . . . . ?
C6 C7 C8 C9 -8.7(2) . . . . ?
C6 C5 C10 C9 49.9(2) . . . . ?
C6 C5 C10 C1 171.09(16) . . . . ?
C6 C5 C10 C14 -70.9(2) . . . . ?
C5 C4 C3 O1 -172.34(19) . . . . ?
C5 C4 C3 C2 9.4(3) . . . . ?
C8 C7 C11 C12 -72.0(2) . . . . ?
C8 C7 C11 C13 53.1(2) . . . . ?
C8 C7 C6 C5 -3.0(3) . . . . ?
C8 C9 C10 C5 -62.16(19) . . . . ?
C8 C9 C10 C1 174.53(16) . . . . ?
C8 C9 C10 C14 57.9(2) . . . . ?
C10 C1 C2 C3 -4.5(3) . . . . ?
C3 C4 C5 C6 178.71(17) . . . . ?
C3 C4 C5 C10 -1.1(3) . . . . ?
C15 C4 C5 C6 -3.3(3) . . . . ?
C15 C4 C5 C10 176.89(18) . . . . ?
C15 C4 C3 O1 9.5(3) . . . . ?
C15 C4 C3 C2 -168.83(18) . . . . ?
C2 C1 C10 C5 12.1(3) . . . . ?
C2 C1 C10 C9 131.5(2) . . . . ?
C2 C1 C10 C14 -108.5(2) . . . . ?
C16 O4 C12 O3 -5.7(3) . . . . ?
C16 O4 C12 C11 177.71(18) . . . . ?

_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_dm16180
_database_code_depnum_ccdc_archive 'CCDC 2002618'
loop_
_audit_author_name
_audit_author_address
'Yao-Yue Fan'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-05-08 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_audit_creation_date             2016-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C25 H30 O6, 0.5(H2 O)'
_chemical_formula_sum            'C25 H31 O6.50'
_chemical_formula_weight         435.50
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
'-x, -y, z'

_cell_length_a                   12.4675(9)
_cell_length_b                   21.6679(15)
_cell_length_c                   9.6367(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2603.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6778
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.391
_cell_measurement_theta_min      4.080
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.881
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.4514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1519 before and 0.0666 after correction.
The Ratio of minimum to maximum transmission is 0.5993.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             932
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16866
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.450
_diffrn_reflns_theta_min         4.080
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                4428
_reflns_number_total             4730
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1765 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4730
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0643P)²+0.0822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1031
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H7A(0.5) H7B(0.5)
3.a Free rotating group:
 O7(H7A,H7B)
3.b Ternary CH refined with riding coordinates:
 C1(H1), C8(H8)
3.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C9(H9A,H9B), C13(H13A,H13B), C1'(H1'A,H1'B)
3.d Aromatic/amide H refined with riding coordinates:
 C5'(H5'), C6'(H6')
3.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C8'(H8'A,H8'B,H8'C), C9'(H9'A,H9'B,
 H9'C), C10'(H10A,H10B,H10C)
3.f Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.057
;
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 -0.59392(15) -0.79695(8) -0.57194(16) 0.0628(4) Uani 1 1 d . . . . .
O2 O -0.31302(11) -0.89193(6) -0.14048(13) 0.0414(3) Uani 1 1 d . . . . .
O3 O -0.11175(11) -0.82696(7) -0.22680(17) 0.0515(4) Uani 1 1 d . . . . .
O4 O -0.01376(12) -0.82817(9) -0.03482(19) 0.0668(5) Uani 1 1 d . . . . .
O5 O -0.3483(2) -0.78093(13) 0.3653(2) 0.0952(8) Uani 1 1 d . . . . .
O6 O -0.07770(14) -0.61232(7) -0.21690(18) 0.0597(4) Uani 1 1 d . . . . .
H6 H -0.0843 -0.6401 -0.2741 0.090 Uiso 1 1 calc GR . . . .
C1 C -0.45823(16) -0.87629(9) -0.2972(2) 0.0428(4) Uani 1 1 d . . . . .
H1 H -0.5054 -0.8967 -0.2300 0.051 Uiso 1 1 calc R . . . .
C2 C -0.51057(19) -0.87909(10) -0.4403(2) 0.0497(5) Uani 1 1 d . . . . .
H2A H -0.4605 -0.8946 -0.5090 0.060 Uiso 1 1 calc R . . . .
H2B H -0.5732 -0.9056 -0.4389 0.060 Uiso 1 1 calc R . . . .
C3 C -0.54186(16) -0.81311(9) -0.4722(2) 0.0453(4) Uani 1 1 d . . . . .
C4 C -0.49918(16) -0.77293(9) -0.3619(2) 0.0425(4) Uani 1 1 d . . . . .
C5 C -0.45402(14) -0.80840(9) -0.2643(2) 0.0395(4) Uani 1 1 d . . . . .
C6 C -0.39365(15) -0.79014(9) -0.1362(2) 0.0417(4) Uani 1 1 d . . . . .
H6A H -0.4357 -0.7994 -0.0542 0.050 Uiso 1 1 calc R . . . .
H6B H -0.3786 -0.7462 -0.1376 0.050 Uiso 1 1 calc R . . . .
C7 C -0.28819(15) -0.82706(8) -0.13431(19) 0.0367(4) Uani 1 1 d . . . . .
C8 C -0.22227(16) -0.81679(9) -0.2671(2) 0.0412(4) Uani 1 1 d . . . . .
H8 H -0.2332 -0.7754 -0.3056 0.049 Uiso 1 1 calc R . . . .
C9 C -0.26041(17) -0.86703(10) -0.3659(2) 0.0464(4) Uani 1 1 d . . . . .
H9A H -0.2014 -0.8936 -0.3930 0.056 Uiso 1 1 calc R . . . .
H9B H -0.2919 -0.8491 -0.4487 0.056 Uiso 1 1 calc R . . . .
C10 C -0.34462(17) -0.90327(8) -0.2832(2) 0.0429(4) Uani 1 1 d . . . . .
C11 C -0.20800(15) -0.81625(9) -0.0143(2) 0.0425(4) Uani 1 1 d . . . . .
C12 C -0.09952(17) -0.82415(9) -0.0885(2) 0.0469(5) Uani 1 1 d . . . . .
C13 C -0.2130(2) -0.86510(11) 0.1014(2) 0.0556(5) Uani 1 1 d . . . . .
H13A H -0.2174 -0.9059 0.0601 0.067 Uiso 1 1 calc R . . . .
H13B H -0.1478 -0.8632 0.1561 0.067 Uiso 1 1 calc R . . . .
C14 C -0.5069(2) -0.70463(11) -0.3740(3) 0.0587(6) Uani 1 1 d . . . . .
H14A H -0.4614 -0.6907 -0.4479 0.088 Uiso 1 1 calc GR . . . .
H14B H -0.4845 -0.6860 -0.2884 0.088 Uiso 1 1 calc GR . . . .
H14C H -0.5797 -0.6932 -0.3934 0.088 Uiso 1 1 calc GR . . . .
C15 C -0.3434(2) -0.97257(10) -0.3068(3) 0.0626(6) Uani 1 1 d . . . . .
H15A H -0.3903 -0.9922 -0.2412 0.094 Uiso 1 1 calc GR . . . .
H15B H -0.2718 -0.9879 -0.2947 0.094 Uiso 1 1 calc GR . . . .
H15C H -0.3674 -0.9814 -0.3993 0.094 Uiso 1 1 calc GR . . . .
C1' C -0.3076(2) -0.85514(14) 0.1939(3) 0.0670(7) Uani 1 1 d . . . . .
H1'A H -0.3054 -0.8847 0.2694 0.080 Uiso 1 1 calc R . . . .
H1'B H -0.3729 -0.8622 0.1416 0.080 Uiso 1 1 calc R . . . .
C2' C -0.30928(19) -0.79098(13) 0.2527(2) 0.0613(6) Uani 1 1 d . . . . .
C3' C -0.26161(16) -0.74006(11) 0.1704(2) 0.0480(5) Uani 1 1 d . . . . .
C4' C -0.21659(15) -0.75103(9) 0.04431(18) 0.0402(4) Uani 1 1 d . . . . .
C5' C -0.17375(15) -0.70146(9) -0.04434(19) 0.0420(4) Uani 1 1 d . . . . .
H5' H -0.1062 -0.7074 -0.0830 0.050 Uiso 1 1 calc R . . . .
C6' C -0.22386(18) -0.64911(10) -0.0734(2) 0.0489(5) Uani 1 1 d . . . . .
H6' H -0.2922 -0.6438 -0.0367 0.059 Uiso 1 1 calc R . . . .
C7' C -0.1795(2) -0.59729(10) -0.1611(2) 0.0568(5) Uani 1 1 d . . . . .
C8' C -0.2582(3) -0.58393(19) -0.2771(4) 0.0967(11) Uani 1 1 d . . . . .
H8'A H -0.2720 -0.6212 -0.3280 0.145 Uiso 1 1 calc GR . . . .
H8'B H -0.2283 -0.5535 -0.3383 0.145 Uiso 1 1 calc GR . . . .
H8'C H -0.3240 -0.5687 -0.2384 0.145 Uiso 1 1 calc GR . . . .
C9' C -0.1608(4) -0.54115(13) -0.0693(4) 0.0978(12) Uani 1 1 d . . . . .
H9'A H -0.1388 -0.5069 -0.1257 0.147 Uiso 1 1 calc GR . . . .
H9'B H -0.1059 -0.5503 -0.0027 0.147 Uiso 1 1 calc GR . . . .
H9'C H -0.2261 -0.5309 -0.0218 0.147 Uiso 1 1 calc GR . . . .
C10' C -0.2689(2) -0.67776(14) 0.2378(2) 0.0652(6) Uani 1 1 d . . . . .
H10A H -0.3389 -0.6607 0.2223 0.098 Uiso 1 1 calc GR . . . .
H10B H -0.2157 -0.6509 0.1986 0.098 Uiso 1 1 calc GR . . . .
H10C H -0.2566 -0.6818 0.3358 0.098 Uiso 1 1 calc GR . . . .
O7 O 0.0000 -0.5000 -0.3595(4) 0.132(2) Uani 1 2 d S T P . .
H7A H -0.0037 -0.5390 -0.3505 0.199 Uiso 0.5 1 d G . . . .
H7B H 0.0396 -0.4852 -0.2960 0.199 Uiso 0.5 1 d G . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.212(2) . ?
O2 C7 1.440(2) . ?
O2 C10 1.451(2) . ?
O3 C8 1.448(3) . ?
O3 C12 1.342(3) . ?
O4 C12 1.191(3) . ?
O5 C2' 1.209(3) . ?
O6 H6 0.8200 . ?
O6 C7' 1.416(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.527(3) . ?
C1 C5 1.506(3) . ?
C1 C10 1.538(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.513(3) . ?
C3 C4 1.473(3) . ?
C4 C5 1.339(3) . ?
C4 C14 1.488(3) . ?
C5 C6 1.499(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.539(3) . ?
C7 C8 1.537(2) . ?
C7 C11 1.547(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.523(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.535(3) . ?
C10 C15 1.519(3) . ?
C11 C12 1.540(3) . ?
C11 C13 1.539(3) . ?
C11 C4' 1.526(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C1' 1.494(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C1' H1'A 0.9700 . ?
C1' H1'B 0.9700 . ?
C1' C2' 1.501(4) . ?
C2' C3' 1.483(3) . ?
C3' C4' 1.359(3) . ?
C3' C10' 1.501(3) . ?
C4' C5' 1.473(3) . ?
C5' H5' 0.9300 . ?
C5' C6' 1.325(3) . ?
C6' H6' 0.9300 . ?
C6' C7' 1.510(3) . ?
C7' C8' 1.515(4) . ?
C7' C9' 1.522(4) . ?
C8' H8'A 0.9600 . ?
C8' H8'B 0.9600 . ?
C8' H8'C 0.9600 . ?
C9' H9'A 0.9600 . ?
C9' H9'B 0.9600 . ?
C9' H9'C 0.9600 . ?
C10' H10A 0.9600 . ?
C10' H10B 0.9600 . ?
C10' H10C 0.9600 . ?
O7 H7A 0.8500 . ?
O7 H7B 0.8498 . ?

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
C7 O2 C10 105.23(13) . . ?
C12 O3 C8 111.53(16) . . ?
C7' O6 H6 109.5 . . ?
C2 C1 H1 108.8 . . ?
C2 C1 C10 117.23(18) . . ?
C5 C1 H1 108.8 . . ?
C5 C1 C2 104.12(15) . . ?
C5 C1 C10 108.70(15) . . ?
C10 C1 H1 108.8 . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 C1 104.81(16) . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
O1 C3 C2 124.87(19) . . ?
O1 C3 C4 126.53(19) . . ?
C4 C3 C2 108.60(16) . . ?
C3 C4 C14 120.52(18) . . ?
C5 C4 C3 108.63(18) . . ?
C5 C4 C14 130.8(2) . . ?
C4 C5 C1 113.47(17) . . ?
C4 C5 C6 129.64(18) . . ?
C6 C5 C1 116.68(16) . . ?
C5 C6 H6A 110.2 . . ?
C5 C6 H6B 110.2 . . ?
C5 C6 C7 107.56(15) . . ?
H6A C6 H6B 108.5 . . ?
C7 C6 H6A 110.2 . . ?
C7 C6 H6B 110.2 . . ?
O2 C7 C6 108.85(14) . . ?
O2 C7 C8 102.82(14) . . ?
O2 C7 C11 108.51(14) . . ?
C6 C7 C11 118.85(15) . . ?
C8 C7 C6 111.81(15) . . ?
C8 C7 C11 104.77(14) . . ?
O3 C8 C7 105.30(15) . . ?
O3 C8 H8 111.9 . . ?
O3 C8 C9 110.86(16) . . ?
C7 C8 H8 111.9 . . ?
C9 C8 C7 104.50(15) . . ?
C9 C8 H8 111.9 . . ?
C8 C9 H9A 110.8 . . ?
C8 C9 H9B 110.8 . . ?
C8 C9 C10 104.72(15) . . ?
H9A C9 H9B 108.9 . . ?
C10 C9 H9A 110.8 . . ?
C10 C9 H9B 110.8 . . ?
O2 C10 C1 105.59(16) . . ?
O2 C10 C9 102.71(15) . . ?
O2 C10 C15 107.86(16) . . ?
C9 C10 C1 112.95(16) . . ?
C15 C10 C1 111.83(17) . . ?
C15 C10 C9 114.9(2) . . ?
C12 C11 C7 101.75(16) . . ?
C13 C11 C7 114.31(15) . . ?
C13 C11 C12 107.20(18) . . ?
C4' C11 C7 111.83(15) . . ?
C4' C11 C12 109.67(15) . . ?
C4' C11 C13 111.48(17) . . ?
O3 C12 C11 111.50(18) . . ?
O4 C12 O3 122.0(2) . . ?
O4 C12 C11 126.5(2) . . ?
C11 C13 H13A 109.3 . . ?
C11 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C1' C13 C11 111.4(2) . . ?
C1' C13 H13A 109.3 . . ?
C1' C13 H13B 109.3 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C1' H1'A 109.3 . . ?
C13 C1' H1'B 109.3 . . ?
C13 C1' C2' 111.7(2) . . ?
H1'A C1' H1'B 107.9 . . ?
C2' C1' H1'A 109.3 . . ?
C2' C1' H1'B 109.3 . . ?
O5 C2' C1' 120.7(2) . . ?
O5 C2' C3' 120.5(3) . . ?
C3' C2' C1' 118.81(19) . . ?
C2' C3' C10' 114.4(2) . . ?
C4' C3' C2' 120.9(2) . . ?
C4' C3' C10' 124.7(2) . . ?
C3' C4' C11 121.45(18) . . ?
C3' C4' C5' 122.74(18) . . ?
C5' C4' C11 115.81(15) . . ?
C4' C5' H5' 117.4 . . ?
C6' C5' C4' 125.18(19) . . ?
C6' C5' H5' 117.4 . . ?
C5' C6' H6' 117.2 . . ?
C5' C6' C7' 125.6(2) . . ?
C7' C6' H6' 117.2 . . ?
O6 C7' C6' 111.69(19) . . ?
O6 C7' C8' 110.1(2) . . ?
O6 C7' C9' 105.5(2) . . ?
C6' C7' C8' 108.5(2) . . ?
C6' C7' C9' 109.0(2) . . ?
C8' C7' C9' 112.0(3) . . ?
C7' C8' H8'A 109.5 . . ?
C7' C8' H8'B 109.5 . . ?
C7' C8' H8'C 109.5 . . ?
H8'A C8' H8'B 109.5 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?
C7' C9' H9'A 109.5 . . ?
C7' C9' H9'B 109.5 . . ?
C7' C9' H9'C 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
C3' C10' H10A 109.5 . . ?
C3' C10' H10B 109.5 . . ?
C3' C10' H10C 109.5 . . ?
H10A C10' H10B 109.5 . . ?
H10A C10' H10C 109.5 . . ?
H10B C10' H10C 109.5 . . ?
H7A O7 H7B 109.5 . . ?

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
O6 H6 O1 0.82 2.02 2.837(2) 174.6 2_534

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 C3 C4 C5 174.9(2) . . . . ?
O1 C3 C4 C14 -7.4(3) . . . . ?
O2 C7 C8 O3 -90.52(16) . . . . ?
O2 C7 C8 C9 26.35(18) . . . . ?
O2 C7 C11 C12 89.79(17) . . . . ?
O2 C7 C11 C13 -25.4(2) . . . . ?
O2 C7 C11 C4' -153.24(15) . . . . ?
O3 C8 C9 C10 112.33(17) . . . . ?
O5 C2' C3' C4' 179.3(2) . . . . ?
O5 C2' C3' C10' -1.1(3) . . . . ?
C1 C2 C3 O1 -173.4(2) . . . . ?
C1 C2 C3 C4 6.2(2) . . . . ?
C1 C5 C6 C7 44.2(2) . . . . ?
C2 C1 C5 C4 2.7(2) . . . . ?
C2 C1 C5 C6 -172.58(16) . . . . ?
C2 C1 C10 O2 177.31(15) . . . . ?
C2 C1 C10 C9 65.8(2) . . . . ?
C2 C1 C10 C15 -65.6(2) . . . . ?
C2 C3 C4 C5 -4.8(2) . . . . ?
C2 C3 C4 C14 173.0(2) . . . . ?
C3 C4 C5 C1 1.2(2) . . . . ?
C3 C4 C5 C6 175.74(18) . . . . ?
C4 C5 C6 C7 -130.2(2) . . . . ?
C5 C1 C2 C3 -5.3(2) . . . . ?
C5 C1 C10 O2 59.68(18) . . . . ?
C5 C1 C10 C9 -51.8(2) . . . . ?
C5 C1 C10 C15 176.73(18) . . . . ?
C5 C6 C7 O2 -56.57(19) . . . . ?
C5 C6 C7 C8 56.34(19) . . . . ?
C5 C6 C7 C11 178.60(15) . . . . ?
C6 C7 C8 O3 152.86(15) . . . . ?
C6 C7 C8 C9 -90.27(18) . . . . ?
C6 C7 C11 C12 -145.22(17) . . . . ?
C6 C7 C11 C13 99.6(2) . . . . ?
C6 C7 C11 C4' -28.2(2) . . . . ?
C7 O2 C10 C1 -75.04(17) . . . . ?
C7 O2 C10 C9 43.51(18) . . . . ?
C7 O2 C10 C15 165.26(18) . . . . ?
C7 C8 C9 C10 -0.6(2) . . . . ?
C7 C11 C12 O3 10.0(2) . . . . ?
C7 C11 C12 O4 -169.2(2) . . . . ?
C7 C11 C13 C1' -76.9(2) . . . . ?
C7 C11 C4' C3' 107.19(19) . . . . ?
C7 C11 C4' C5' -72.5(2) . . . . ?
C8 O3 C12 O4 -176.1(2) . . . . ?
C8 O3 C12 C11 4.6(2) . . . . ?
C8 C7 C11 C12 -19.49(17) . . . . ?
C8 C7 C11 C13 -134.66(18) . . . . ?
C8 C7 C11 C4' 97.48(17) . . . . ?
C8 C9 C10 O2 -25.07(19) . . . . ?
C8 C9 C10 C1 88.18(19) . . . . ?
C8 C9 C10 C15 -141.90(18) . . . . ?
C10 O2 C7 C6 74.75(17) . . . . ?
C10 O2 C7 C8 -43.96(18) . . . . ?
C10 O2 C7 C11 -154.56(15) . . . . ?
C10 C1 C2 C3 -125.34(19) . . . . ?
C10 C1 C5 C4 128.38(18) . . . . ?
C10 C1 C5 C6 -46.9(2) . . . . ?
C11 C7 C8 O3 22.85(17) . . . . ?
C11 C7 C8 C9 139.72(16) . . . . ?
C11 C13 C1' C2' -54.8(3) . . . . ?
C11 C4' C5' C6' 132.5(2) . . . . ?
C12 O3 C8 C7 -17.5(2) . . . . ?
C12 O3 C8 C9 -129.96(17) . . . . ?
C12 C11 C13 C1' 171.16(18) . . . . ?
C12 C11 C4' C3' -140.73(19) . . . . ?
C12 C11 C4' C5' 39.5(2) . . . . ?
C13 C11 C12 O3 130.31(18) . . . . ?
C13 C11 C12 O4 -48.9(3) . . . . ?
C13 C11 C4' C3' -22.2(2) . . . . ?
C13 C11 C4' C5' 158.11(18) . . . . ?
C13 C1' C2' O5 -149.8(2) . . . . ?
C13 C1' C2' C3' 29.8(3) . . . . ?
C14 C4 C5 C1 -176.2(2) . . . . ?
C14 C4 C5 C6 -1.7(4) . . . . ?
C1' C2' C3' C4' -0.3(3) . . . . ?
C1' C2' C3' C10' 179.2(2) . . . . ?
C2' C3' C4' C11 -3.2(3) . . . . ?
C2' C3' C4' C5' 176.50(19) . . . . ?
C3' C4' C5' C6' -47.2(3) . . . . ?
C4' C11 C12 O3 -108.51(18) . . . . ?
C4' C11 C12 O4 72.3(3) . . . . ?
C4' C11 C13 C1' 51.1(2) . . . . ?
C4' C5' C6' C7' 178.31(19) . . . . ?
C5' C6' C7' O6 3.2(3) . . . . ?
C5' C6' C7' C8' 124.8(3) . . . . ?
C5' C6' C7' C9' -113.0(3) . . . . ?
C10' C3' C4' C11 177.3(2) . . . . ?
C10' C3' C4' C5' -3.0(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.611 246.4 69.1 ?
2 0.500 0.500 -0.448 246.4 69.1 ?

_shelx_SHELXL_version_number     2014/7
_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_cu_dm16184_0m
_database_code_depnum_ccdc_archive 'CCDC 2002619'
loop_
_audit_author_name
_audit_author_address
'Yao-Yue Fan'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-05-08 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_audit_creation_date             2016-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H32 O5'
_chemical_formula_sum            'C25 H32 O5'
_chemical_formula_weight         412.50
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   9.1977(11)
_cell_length_b                   9.2073(11)
_cell_length_c                   26.829(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2272.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7062
_cell_measurement_temperature    296
_cell_measurement_theta_max      69.403
_cell_measurement_theta_min      5.079
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.924
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0856 before and 0.0430 after correction.
The Ratio of minimum to maximum transmission is 0.8815.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15484
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.067
_diffrn_reflns_theta_min         3.294
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                3934
_reflns_number_total             4104
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1576 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(7)
_refine_ls_extinction_coef       0.0047(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+0.2130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0939
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C8(H8), C4'(H4')
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C9(H9A,H9B), C13(H13A,H13B), C1'(H1'A,H1'B)
2.c Aromatic/amide H refined with riding coordinates:
 C2'(H2'), C5'(H5'), C6'(H6')
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C8'(H8'A,H8'B,H8'C), C9'(H9'A,H9'B,
 H9'C), C10'(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.7491(2) 0.9593(2) 0.48798(7) 0.0821(6) Uani 1 1 d . . . . .
O2 O 0.97293(15) 0.58330(16) 0.33604(5) 0.0496(3) Uani 1 1 d . . . . .
O3 O 0.87549(18) 0.32172(16) 0.39447(6) 0.0548(4) Uani 1 1 d . . . . .
O4 O 0.8832(3) 0.14982(18) 0.33656(8) 0.0837(6) Uani 1 1 d . . . . .
O5 O 0.3832(3) 0.4249(2) 0.42777(7) 0.0909(7) Uani 1 1 d . . . . .
H5 H 0.3438 0.4413 0.4546 0.136 Uiso 1 1 calc GR . . . .
C1 C 0.9277(2) 0.8056(2) 0.38067(8) 0.0468(5) Uani 1 1 d . . . . .
H1 H 0.9554 0.8629 0.3514 0.056 Uiso 1 1 calc R . . . .
C2 C 0.9377(2) 0.9012(3) 0.42763(9) 0.0574(6) Uani 1 1 d . . . . .
H2A H 1.0055 0.8600 0.4514 0.069 Uiso 1 1 calc R . . . .
H2B H 0.9694 0.9986 0.4191 0.069 Uiso 1 1 calc R . . . .
C3 C 0.7864(3) 0.9036(2) 0.44869(8) 0.0551(5) Uani 1 1 d . . . . .
C4 C 0.6901(2) 0.8222(2) 0.41530(8) 0.0475(5) Uani 1 1 d . . . . .
C5 C 0.7693(2) 0.7683(2) 0.37758(7) 0.0409(4) Uani 1 1 d . . . . .
C6 C 0.7252(2) 0.6609(2) 0.33881(7) 0.0426(4) Uani 1 1 d . . . . .
H6A H 0.7343 0.7029 0.3058 0.051 Uiso 1 1 calc R . . . .
H6B H 0.6251 0.6311 0.3438 0.051 Uiso 1 1 calc R . . . .
C7 C 0.8283(2) 0.5300(2) 0.34449(7) 0.0408(4) Uani 1 1 d . . . . .
C8 C 0.8379(2) 0.4740(2) 0.39887(7) 0.0436(4) Uani 1 1 d . . . . .
H8 H 0.7464 0.4880 0.4169 0.052 Uiso 1 1 calc R . . . .
C9 C 0.9623(2) 0.5586(2) 0.42240(9) 0.0547(5) Uani 1 1 d . . . . .
H9A H 1.0400 0.4939 0.4326 0.066 Uiso 1 1 calc R . . . .
H9B H 0.9290 0.6130 0.4512 0.066 Uiso 1 1 calc R . . . .
C10 C 1.0134(2) 0.6612(2) 0.38076(8) 0.0510(5) Uani 1 1 d . . . . .
C11 C 0.8022(2) 0.3923(2) 0.31304(7) 0.0476(5) Uani 1 1 d . . . . .
C12 C 0.8589(3) 0.2739(2) 0.34731(9) 0.0565(5) Uani 1 1 d . . . . .
C13 C 0.8857(3) 0.3914(3) 0.26304(9) 0.0636(6) Uani 1 1 d . . . . .
H13A H 0.9878 0.4106 0.2692 0.076 Uiso 1 1 calc R . . . .
H13B H 0.8777 0.2961 0.2478 0.076 Uiso 1 1 calc R . . . .
C14 C 0.5329(3) 0.8005(3) 0.42587(11) 0.0704(7) Uani 1 1 d . . . . .
H14A H 0.4763 0.8394 0.3989 0.106 Uiso 1 1 calc GR . . . .
H14B H 0.5077 0.8496 0.4562 0.106 Uiso 1 1 calc GR . . . .
H14C H 0.5131 0.6986 0.4293 0.106 Uiso 1 1 calc GR . . . .
C15 C 1.1765(2) 0.6873(3) 0.37949(13) 0.0750(8) Uani 1 1 d . . . . .
H15A H 1.2263 0.5958 0.3773 0.113 Uiso 1 1 calc GR . . . .
H15B H 1.2058 0.7368 0.4093 0.113 Uiso 1 1 calc GR . . . .
H15C H 1.2005 0.7456 0.3510 0.113 Uiso 1 1 calc GR . . . .
C1' C 0.8257(3) 0.5051(3) 0.22759(9) 0.0682(7) Uani 1 1 d . . . . .
H1'A H 0.8580 0.6004 0.2383 0.082 Uiso 1 1 calc R . . . .
H1'B H 0.8645 0.4878 0.1945 0.082 Uiso 1 1 calc R . . . .
C2' C 0.6651(3) 0.5038(3) 0.22522(8) 0.0635(7) Uani 1 1 d . . . . .
H2' H 0.6211 0.5528 0.1989 0.076 Uiso 1 1 calc R . . . .
C3' C 0.5786(3) 0.4372(2) 0.25810(8) 0.0553(6) Uani 1 1 d . . . . .
C4' C 0.6401(3) 0.3533(2) 0.30247(7) 0.0476(5) Uani 1 1 d . . . . .
H4' H 0.6399 0.2510 0.2925 0.057 Uiso 1 1 calc R . . . .
C5' C 0.5433(2) 0.3624(2) 0.34786(7) 0.0452(4) Uani 1 1 d . . . . .
H5' H 0.5003 0.4520 0.3541 0.054 Uiso 1 1 calc R . . . .
C6' C 0.5133(2) 0.2576(2) 0.37942(7) 0.0461(4) Uani 1 1 d . . . . .
H6' H 0.5540 0.1667 0.3736 0.055 Uiso 1 1 calc R . . . .
C7' C 0.4173(3) 0.2755(2) 0.42438(8) 0.0528(5) Uani 1 1 d . . . . .
C8' C 0.4952(4) 0.2285(4) 0.47115(9) 0.0829(9) Uani 1 1 d . . . . .
H8'A H 0.5762 0.2919 0.4771 0.124 Uiso 1 1 calc GR . . . .
H8'B H 0.5296 0.1307 0.4672 0.124 Uiso 1 1 calc GR . . . .
H8'C H 0.4295 0.2329 0.4989 0.124 Uiso 1 1 calc GR . . . .
C9' C 0.2788(4) 0.1889(5) 0.41656(15) 0.1080(13) Uani 1 1 d . . . . .
H9'A H 0.2165 0.2003 0.4450 0.162 Uiso 1 1 calc GR . . . .
H9'B H 0.3025 0.0881 0.4124 0.162 Uiso 1 1 calc GR . . . .
H9'C H 0.2297 0.2235 0.3873 0.162 Uiso 1 1 calc GR . . . .
C10' C 0.4165(3) 0.4362(3) 0.25276(11) 0.0771(8) Uani 1 1 d . . . . .
H10A H 0.3811 0.3387 0.2565 0.116 Uiso 1 1 calc GR . . . .
H10B H 0.3904 0.4724 0.2204 0.116 Uiso 1 1 calc GR . . . .
H10C H 0.3741 0.4969 0.2780 0.116 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.221(3) . ?
O2 C7 1.436(2) . ?
O2 C10 1.446(3) . ?
O3 C8 1.449(2) . ?
O3 C12 1.348(3) . ?
O4 C12 1.200(3) . ?
O5 H5 0.8200 . ?
O5 C7' 1.414(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.540(3) . ?
C1 C5 1.499(3) . ?
C1 C10 1.546(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.501(3) . ?
C3 C4 1.466(3) . ?
C4 C5 1.342(3) . ?
C4 C14 1.487(3) . ?
C5 C6 1.491(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.541(2) . ?
C7 C8 1.550(3) . ?
C7 C11 1.542(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.521(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.537(3) . ?
C10 C15 1.520(3) . ?
C11 C12 1.519(3) . ?
C11 C13 1.546(3) . ?
C11 C4' 1.559(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C1' 1.518(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C1' H1'A 0.9700 . ?
C1' H1'B 0.9700 . ?
C1' C2' 1.478(4) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.336(4) . ?
C3' C4' 1.528(3) . ?
C3' C10' 1.498(4) . ?
C4' H4' 0.9800 . ?
C4' C5' 1.511(3) . ?
C5' H5' 0.9300 . ?
C5' C6' 1.313(3) . ?
C6' H6' 0.9300 . ?
C6' C7' 1.504(3) . ?
C7' C8' 1.509(4) . ?
C7' C9' 1.518(4) . ?
C8' H8'A 0.9600 . ?
C8' H8'B 0.9600 . ?
C8' H8'C 0.9600 . ?
C9' H9'A 0.9600 . ?
C9' H9'B 0.9600 . ?
C9' H9'C 0.9600 . ?
C10' H10A 0.9600 . ?
C10' H10B 0.9600 . ?
C10' H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 C10 106.07(15) . . ?
C12 O3 C8 111.43(15) . . ?
C7' O5 H5 109.5 . . ?
C2 C1 H1 109.4 . . ?
C2 C1 C10 117.39(17) . . ?
C5 C1 H1 109.4 . . ?
C5 C1 C2 103.54(17) . . ?
C5 C1 C10 107.39(16) . . ?
C10 C1 H1 109.4 . . ?
C1 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 C1 105.14(17) . . ?
C3 C2 H2A 110.7 . . ?
C3 C2 H2B 110.7 . . ?
O1 C3 C2 126.3(2) . . ?
O1 C3 C4 124.9(2) . . ?
C4 C3 C2 108.80(19) . . ?
C3 C4 C14 122.7(2) . . ?
C5 C4 C3 108.80(19) . . ?
C5 C4 C14 128.43(19) . . ?
C4 C5 C1 113.63(18) . . ?
C4 C5 C6 128.62(19) . . ?
C6 C5 C1 117.02(17) . . ?
C5 C6 H6A 110.4 . . ?
C5 C6 H6B 110.4 . . ?
C5 C6 C7 106.41(15) . . ?
H6A C6 H6B 108.6 . . ?
C7 C6 H6A 110.4 . . ?
C7 C6 H6B 110.4 . . ?
O2 C7 C6 106.68(15) . . ?
O2 C7 C8 102.09(15) . . ?
O2 C7 C11 109.82(15) . . ?
C6 C7 C8 112.87(15) . . ?
C6 C7 C11 119.54(16) . . ?
C11 C7 C8 104.51(15) . . ?
O3 C8 C7 105.01(16) . . ?
O3 C8 H8 111.9 . . ?
O3 C8 C9 110.49(17) . . ?
C7 C8 H8 111.9 . . ?
C9 C8 C7 105.26(16) . . ?
C9 C8 H8 111.9 . . ?
C8 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
C8 C9 C10 104.06(16) . . ?
H9A C9 H9B 109.0 . . ?
C10 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
O2 C10 C1 107.09(15) . . ?
O2 C10 C9 102.69(17) . . ?
O2 C10 C15 108.3(2) . . ?
C9 C10 C1 111.96(18) . . ?
C15 C10 C1 111.6(2) . . ?
C15 C10 C9 114.54(19) . . ?
C7 C11 C13 113.73(19) . . ?
C7 C11 C4' 115.98(15) . . ?
C12 C11 C7 101.84(17) . . ?
C12 C11 C13 110.52(17) . . ?
C12 C11 C4' 105.87(18) . . ?
C13 C11 C4' 108.41(19) . . ?
O3 C12 C11 111.89(17) . . ?
O4 C12 O3 121.0(2) . . ?
O4 C12 C11 127.0(2) . . ?
C11 C13 H13A 109.4 . . ?
C11 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C1' C13 C11 111.04(19) . . ?
C1' C13 H13A 109.4 . . ?
C1' C13 H13B 109.4 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C1' H1'A 109.1 . . ?
C13 C1' H1'B 109.1 . . ?
H1'A C1' H1'B 107.8 . . ?
C2' C1' C13 112.6(2) . . ?
C2' C1' H1'A 109.1 . . ?
C2' C1' H1'B 109.1 . . ?
C1' C2' H2' 117.6 . . ?
C3' C2' C1' 124.8(2) . . ?
C3' C2' H2' 117.6 . . ?
C2' C3' C4' 121.7(2) . . ?
C2' C3' C10' 122.2(2) . . ?
C10' C3' C4' 116.1(2) . . ?
C11 C4' H4' 105.8 . . ?
C3' C4' C11 112.27(18) . . ?
C3' C4' H4' 105.8 . . ?
C5' C4' C11 113.82(16) . . ?
C5' C4' C3' 112.47(18) . . ?
C5' C4' H4' 105.8 . . ?
C4' C5' H5' 116.5 . . ?
C6' C5' C4' 127.09(18) . . ?
C6' C5' H5' 116.5 . . ?
C5' C6' H6' 118.0 . . ?
C5' C6' C7' 124.08(19) . . ?
C7' C6' H6' 118.0 . . ?
O5 C7' C6' 106.75(18) . . ?
O5 C7' C8' 109.3(2) . . ?
O5 C7' C9' 109.5(3) . . ?
C6' C7' C8' 110.9(2) . . ?
C6' C7' C9' 109.0(2) . . ?
C8' C7' C9' 111.3(3) . . ?
C7' C8' H8'A 109.5 . . ?
C7' C8' H8'B 109.5 . . ?
C7' C8' H8'C 109.5 . . ?
H8'A C8' H8'B 109.5 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?
C7' C9' H9'A 109.5 . . ?
C7' C9' H9'B 109.5 . . ?
C7' C9' H9'C 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
C3' C10' H10A 109.5 . . ?
C3' C10' H10B 109.5 . . ?
C3' C10' H10C 109.5 . . ?
H10A C10' H10B 109.5 . . ?
H10A C10' H10C 109.5 . . ?
H10B C10' H10C 109.5 . . ?

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
O5 H5 O1 0.82 1.99 2.787(2) 163.0 4_466

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 C3 C4 C5 -175.8(2) . . . . ?
O1 C3 C4 C14 0.9(4) . . . . ?
O2 C7 C8 O3 -92.59(17) . . . . ?
O2 C7 C8 C9 24.08(19) . . . . ?
O2 C7 C11 C12 87.07(18) . . . . ?
O2 C7 C11 C13 -31.8(2) . . . . ?
O2 C7 C11 C4' -158.55(15) . . . . ?
O3 C8 C9 C10 114.56(18) . . . . ?
C1 C2 C3 O1 174.6(2) . . . . ?
C1 C2 C3 C4 -3.0(2) . . . . ?
C1 C5 C6 C7 49.7(2) . . . . ?
C2 C1 C5 C4 -2.0(2) . . . . ?
C2 C1 C5 C6 -173.05(16) . . . . ?
C2 C1 C10 O2 172.98(17) . . . . ?
C2 C1 C10 C9 61.2(2) . . . . ?
C2 C1 C10 C15 -68.7(3) . . . . ?
C2 C3 C4 C5 1.9(3) . . . . ?
C2 C3 C4 C14 178.5(2) . . . . ?
C3 C4 C5 C1 0.2(2) . . . . ?
C3 C4 C5 C6 169.93(19) . . . . ?
C4 C5 C6 C7 -119.8(2) . . . . ?
C5 C1 C2 C3 2.9(2) . . . . ?
C5 C1 C10 O2 57.0(2) . . . . ?
C5 C1 C10 C9 -54.9(2) . . . . ?
C5 C1 C10 C15 175.3(2) . . . . ?
C5 C6 C7 O2 -60.74(19) . . . . ?
C5 C6 C7 C8 50.6(2) . . . . ?
C5 C6 C7 C11 174.05(17) . . . . ?
C6 C7 C8 O3 153.27(16) . . . . ?
C6 C7 C8 C9 -90.1(2) . . . . ?
C6 C7 C11 C12 -149.23(18) . . . . ?
C6 C7 C11 C13 91.9(2) . . . . ?
C6 C7 C11 C4' -34.8(2) . . . . ?
C7 O2 C10 C1 -73.58(17) . . . . ?
C7 O2 C10 C9 44.47(18) . . . . ?
C7 O2 C10 C15 165.98(17) . . . . ?
C7 C8 C9 C10 1.7(2) . . . . ?
C7 C11 C12 O3 15.3(2) . . . . ?
C7 C11 C12 O4 -167.4(3) . . . . ?
C7 C11 C13 C1' -68.6(3) . . . . ?
C7 C11 C4' C3' 83.3(2) . . . . ?
C7 C11 C4' C5' -45.9(2) . . . . ?
C8 O3 C12 O4 -179.1(2) . . . . ?
C8 O3 C12 C11 -1.5(3) . . . . ?
C8 C7 C11 C12 -21.79(19) . . . . ?
C8 C7 C11 C13 -140.69(18) . . . . ?
C8 C7 C11 C4' 92.60(19) . . . . ?
C8 C9 C10 O2 -26.8(2) . . . . ?
C8 C9 C10 C1 87.8(2) . . . . ?
C8 C9 C10 C15 -143.9(2) . . . . ?
C10 O2 C7 C6 75.73(17) . . . . ?
C10 O2 C7 C8 -42.89(17) . . . . ?
C10 O2 C7 C11 -153.35(15) . . . . ?
C10 C1 C2 C3 -115.2(2) . . . . ?
C10 C1 C5 C4 122.83(19) . . . . ?
C10 C1 C5 C6 -48.2(2) . . . . ?
C11 C7 C8 O3 21.8(2) . . . . ?
C11 C7 C8 C9 138.51(17) . . . . ?
C11 C13 C1' C2' -46.1(3) . . . . ?
C11 C4' C5' C6' -90.7(2) . . . . ?
C12 O3 C8 C7 -13.1(2) . . . . ?
C12 O3 C8 C9 -126.1(2) . . . . ?
C12 C11 C13 C1' 177.6(2) . . . . ?
C12 C11 C4' C3' -164.66(17) . . . . ?
C12 C11 C4' C5' 66.1(2) . . . . ?
C13 C11 C12 O3 136.4(2) . . . . ?
C13 C11 C12 O4 -46.2(4) . . . . ?
C13 C11 C4' C3' -46.1(2) . . . . ?
C13 C11 C4' C5' -175.28(17) . . . . ?
C13 C1' C2' C3' 15.1(4) . . . . ?
C14 C4 C5 C1 -176.3(2) . . . . ?
C14 C4 C5 C6 -6.5(4) . . . . ?
C1' C2' C3' C4' -0.2(4) . . . . ?
C1' C2' C3' C10' -178.1(2) . . . . ?
C2' C3' C4' C11 16.7(3) . . . . ?
C2' C3' C4' C5' 146.6(2) . . . . ?
C3' C4' C5' C6' 140.1(2) . . . . ?
C4' C11 C12 O3 -106.4(2) . . . . ?
C4' C11 C12 O4 71.0(3) . . . . ?
C4' C11 C13 C1' 62.0(3) . . . . ?
C4' C5' C6' C7' 179.1(2) . . . . ?
C5' C6' C7' O5 -6.3(3) . . . . ?
C5' C6' C7' C8' -125.3(3) . . . . ?
C5' C6' C7' C9' 111.8(3) . . . . ?
C10' C3' C4' C11 -165.3(2) . . . . ?
C10' C3' C4' C5' -35.3(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_mj20178_0m
_database_code_depnum_ccdc_archive 'CCDC 2002639'
loop_
_audit_author_name
_audit_author_address
'Cheng-Yu Zheng'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-05-08 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_audit_creation_date             2020-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H32 O5'
_chemical_formula_sum            'C25 H32 O5'
_chemical_formula_weight         412.50
_chemical_absolute_configuration rmad
_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 0.0148 0.0070 '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 0.0412 0.0250 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   9.1292(6)
_cell_length_b                   9.1825(6)
_cell_length_c                   26.7030(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2238.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      54.90
_cell_measurement_theta_min      2.88
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.435
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1337 before and 0.0828 after correction.
The Ratio of minimum to maximum transmission is 0.6141.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19853
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.067
_diffrn_reflns_theta_min         2.879
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                3445
_reflns_number_total             4207
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1223 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+1.0245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1352
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C8(H8), C4'(H4')
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C9(H9A,H9B), C13(H13A,H13B), C1'(H1'A,H1'B)
2.c Aromatic/amide H refined with riding coordinates:
 C2'(H2'), C5'(H5'), C6'(H6')
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C8'(H8'A,H8'B,H8'C), C9'(H9'A,H9'B,
 H9'C), C10'(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.7089(4) 0.5015(3) 0.73873(11) 0.0672(9) Uani 1 1 d . . . . .
O2 O 0.3328(3) 0.2764(3) 0.58555(9) 0.0434(6) Uani 1 1 d . . . . .
O3 O 0.0688(3) 0.3750(3) 0.64402(10) 0.0480(6) Uani 1 1 d . . . . .
O4 O -0.1038(3) 0.3672(4) 0.58551(12) 0.0683(9) Uani 1 1 d . . . . .
O5 O 0.1747(3) 0.8675(4) 0.67753(12) 0.0778(10) Uani 1 1 d . . . . .
H5 H 0.192377 0.905489 0.705495 0.117 Uiso 1 1 calc GR . . . .
C1 C 0.5561(4) 0.3220(4) 0.63091(14) 0.0413(8) Uani 1 1 d . . . . .
H1 H 0.615771 0.293465 0.601087 0.050 Uiso 1 1 calc R . . . .
C2 C 0.6512(4) 0.3118(4) 0.67798(15) 0.0496(10) Uani 1 1 d . . . . .
H2A H 0.608483 0.242305 0.702278 0.060 Uiso 1 1 calc R . . . .
H2B H 0.751594 0.279518 0.669429 0.060 Uiso 1 1 calc R . . . .
C3 C 0.6529(4) 0.4633(4) 0.69914(15) 0.0480(9) Uani 1 1 d . . . . .
C4 C 0.5720(4) 0.5603(4) 0.66549(14) 0.0415(8) Uani 1 1 d . . . . .
C5 C 0.5187(4) 0.4810(4) 0.62741(13) 0.0382(8) Uani 1 1 d . . . . .
C6 C 0.4112(4) 0.5249(4) 0.58816(13) 0.0400(8) Uani 1 1 d . . . . .
H6A H 0.454850 0.514919 0.554401 0.048 Uiso 1 1 calc R . . . .
H6B H 0.380833 0.627491 0.592999 0.048 Uiso 1 1 calc R . . . .
C7 C 0.2789(4) 0.4222(4) 0.59393(14) 0.0391(8) Uani 1 1 d . . . . .
C8 C 0.2222(4) 0.4126(4) 0.64844(13) 0.0390(8) Uani 1 1 d . . . . .
H8 H 0.236740 0.505973 0.667060 0.047 Uiso 1 1 calc R . . . .
C9 C 0.3072(4) 0.2871(4) 0.67208(15) 0.0490(9) Uani 1 1 d . . . . .
H9A H 0.240220 0.207617 0.682285 0.059 Uiso 1 1 calc R . . . .
H9B H 0.362600 0.320591 0.701788 0.059 Uiso 1 1 calc R . . . .
C10 C 0.4115(4) 0.2359(4) 0.63062(14) 0.0464(9) Uani 1 1 d . . . . .
C11 C 0.1409(4) 0.4482(4) 0.56222(13) 0.0422(9) Uani 1 1 d . . . . .
C12 C 0.0214(4) 0.3919(4) 0.59648(15) 0.0492(9) Uani 1 1 d . . . . .
C13 C 0.1405(5) 0.3649(5) 0.51229(15) 0.0552(11) Uani 1 1 d . . . . .
H13A H 0.159941 0.260442 0.518695 0.066 Uiso 1 1 calc R . . . .
H13B H 0.042684 0.373133 0.496558 0.066 Uiso 1 1 calc R . . . .
C14 C 0.5494(5) 0.7188(4) 0.67579(18) 0.0612(12) Uani 1 1 d . . . . .
H14A H 0.592875 0.776402 0.648704 0.092 Uiso 1 1 calc GR . . . .
H14B H 0.596228 0.744499 0.707611 0.092 Uiso 1 1 calc GR . . . .
H14C H 0.444222 0.739431 0.677811 0.092 Uiso 1 1 calc GR . . . .
C15 C 0.4368(5) 0.0724(4) 0.62926(19) 0.0623(12) Uani 1 1 d . . . . .
H15A H 0.342299 0.022086 0.627194 0.093 Uiso 1 1 calc GR . . . .
H15B H 0.488054 0.042076 0.659773 0.093 Uiso 1 1 calc GR . . . .
H15C H 0.496304 0.047550 0.599938 0.093 Uiso 1 1 calc GR . . . .
C1' C 0.2555(5) 0.4241(5) 0.47681(16) 0.0578(11) Uani 1 1 d . . . . .
H1'A H 0.353371 0.390430 0.487756 0.069 Uiso 1 1 calc R . . . .
H1'B H 0.237487 0.385021 0.442812 0.069 Uiso 1 1 calc R . . . .
C2' C 0.2546(4) 0.5864(5) 0.47478(15) 0.0538(11) Uani 1 1 d . . . . .
H2' H 0.305971 0.631847 0.448086 0.065 Uiso 1 1 calc R . . . .
C3' C 0.1870(4) 0.6721(5) 0.50759(14) 0.0475(10) Uani 1 1 d . . . . .
C4' C 0.1019(4) 0.6106(4) 0.55175(13) 0.0415(8) Uani 1 1 d . . . . .
H4' H -0.003302 0.611106 0.541353 0.050 Uiso 1 1 calc R . . . .
C5' C 0.1109(4) 0.7071(4) 0.59739(13) 0.0420(8) Uani 1 1 d . . . . .
H5' H 0.203112 0.751179 0.603854 0.050 Uiso 1 1 calc R . . . .
C6' C 0.0049(4) 0.7368(4) 0.62926(13) 0.0425(8) Uani 1 1 d . . . . .
H6' H -0.088875 0.695268 0.623415 0.051 Uiso 1 1 calc R . . . .
C7' C 0.0240(4) 0.8329(4) 0.67435(14) 0.0480(9) Uani 1 1 d . . . . .
C8' C -0.0640(7) 0.9719(5) 0.6669(2) 0.0859(16) Uani 1 1 d . . . . .
H8'A H -0.054698 1.033553 0.696698 0.129 Uiso 1 1 calc GR . . . .
H8'B H -0.167283 0.947232 0.661640 0.129 Uiso 1 1 calc GR . . . .
H8'C H -0.026667 1.024379 0.637623 0.129 Uiso 1 1 calc GR . . . .
C9' C -0.0231(6) 0.7545(6) 0.72128(15) 0.0683(13) Uani 1 1 d . . . . .
H9'A H -0.013912 0.820167 0.750048 0.102 Uiso 1 1 calc GR . . . .
H9'B H 0.039253 0.668965 0.726428 0.102 Uiso 1 1 calc GR . . . .
H9'C H -0.125352 0.723497 0.717875 0.102 Uiso 1 1 calc GR . . . .
C10' C 0.1861(6) 0.8353(5) 0.50245(17) 0.0632(12) Uani 1 1 d . . . . .
H10A H 0.086234 0.871724 0.507253 0.095 Uiso 1 1 calc GR . . . .
H10B H 0.220809 0.862271 0.468986 0.095 Uiso 1 1 calc GR . . . .
H10C H 0.250803 0.878071 0.527783 0.095 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.225(5) . ?
O2 C7 1.444(4) . ?
O2 C10 1.450(5) . ?
O3 C8 1.447(4) . ?
O3 C12 1.350(5) . ?
O4 C12 1.202(5) . ?
O5 H5 0.8400 . ?
O5 C7' 1.414(5) . ?
C1 H1 1.0000 . ?
C1 C2 1.530(5) . ?
C1 C5 1.502(5) . ?
C1 C10 1.539(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.502(5) . ?
C3 C4 1.465(5) . ?
C4 C5 1.342(5) . ?
C4 C14 1.496(5) . ?
C5 C6 1.491(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.540(5) . ?
C7 C8 1.548(5) . ?
C7 C11 1.536(5) . ?
C8 H8 1.0000 . ?
C8 C9 1.526(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.534(5) . ?
C10 C15 1.519(5) . ?
C11 C12 1.514(5) . ?
C11 C13 1.537(5) . ?
C11 C4' 1.558(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C1' 1.515(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C1' H1'A 0.9900 . ?
C1' H1'B 0.9900 . ?
C1' C2' 1.491(6) . ?
C2' H2' 0.9500 . ?
C2' C3' 1.329(6) . ?
C3' C4' 1.521(5) . ?
C3' C10' 1.505(6) . ?
C4' H4' 1.0000 . ?
C4' C5' 1.509(5) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.318(5) . ?
C6' H6' 0.9500 . ?
C6' C7' 1.503(5) . ?
C7' C8' 1.521(6) . ?
C7' C9' 1.508(6) . ?
C8' H8'A 0.9800 . ?
C8' H8'B 0.9800 . ?
C8' H8'C 0.9800 . ?
C9' H9'A 0.9800 . ?
C9' H9'B 0.9800 . ?
C9' H9'C 0.9800 . ?
C10' H10A 0.9800 . ?
C10' H10B 0.9800 . ?
C10' H10C 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
C7 O2 C10 106.1(3) . . ?
C12 O3 C8 111.1(3) . . ?
C7' O5 H5 109.5 . . ?
C2 C1 H1 109.2 . . ?
C2 C1 C10 117.3(3) . . ?
C5 C1 H1 109.2 . . ?
C5 C1 C2 103.9(3) . . ?
C5 C1 C10 107.7(3) . . ?
C10 C1 H1 109.2 . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 C1 105.0(3) . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
O1 C3 C2 126.4(4) . . ?
O1 C3 C4 124.5(4) . . ?
C4 C3 C2 109.1(3) . . ?
C3 C4 C14 123.2(3) . . ?
C5 C4 C3 108.6(3) . . ?
C5 C4 C14 128.1(3) . . ?
C4 C5 C1 113.4(3) . . ?
C4 C5 C6 128.7(3) . . ?
C6 C5 C1 117.2(3) . . ?
C5 C6 H6A 110.5 . . ?
C5 C6 H6B 110.5 . . ?
C5 C6 C7 106.3(3) . . ?
H6A C6 H6B 108.7 . . ?
C7 C6 H6A 110.5 . . ?
C7 C6 H6B 110.5 . . ?
O2 C7 C6 106.6(3) . . ?
O2 C7 C8 101.9(3) . . ?
O2 C7 C11 109.8(3) . . ?
C6 C7 C8 113.0(3) . . ?
C11 C7 C6 119.5(3) . . ?
C11 C7 C8 104.6(3) . . ?
O3 C8 C7 105.1(3) . . ?
O3 C8 H8 112.0 . . ?
O3 C8 C9 110.2(3) . . ?
C7 C8 H8 112.0 . . ?
C9 C8 C7 105.2(3) . . ?
C9 C8 H8 112.0 . . ?
C8 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
C8 C9 C10 104.4(3) . . ?
H9A C9 H9B 108.9 . . ?
C10 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
O2 C10 C1 107.3(3) . . ?
O2 C10 C9 102.3(3) . . ?
O2 C10 C15 108.0(3) . . ?
C9 C10 C1 111.8(3) . . ?
C15 C10 C1 112.2(3) . . ?
C15 C10 C9 114.5(3) . . ?
C7 C11 C13 113.7(3) . . ?
C7 C11 C4' 115.7(3) . . ?
C12 C11 C7 101.8(3) . . ?
C12 C11 C13 110.6(3) . . ?
C12 C11 C4' 105.7(3) . . ?
C13 C11 C4' 108.7(3) . . ?
O3 C12 C11 112.1(3) . . ?
O4 C12 O3 120.8(4) . . ?
O4 C12 C11 127.0(4) . . ?
C11 C13 H13A 109.4 . . ?
C11 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C1' C13 C11 111.2(3) . . ?
C1' C13 H13A 109.4 . . ?
C1' C13 H13B 109.4 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C1' H1'A 109.2 . . ?
C13 C1' H1'B 109.2 . . ?
H1'A C1' H1'B 107.9 . . ?
C2' C1' C13 112.2(4) . . ?
C2' C1' H1'A 109.2 . . ?
C2' C1' H1'B 109.2 . . ?
C1' C2' H2' 117.6 . . ?
C3' C2' C1' 124.8(4) . . ?
C3' C2' H2' 117.6 . . ?
C2' C3' C4' 121.9(4) . . ?
C2' C3' C10' 122.1(4) . . ?
C10' C3' C4' 116.0(4) . . ?
C11 C4' H4' 105.9 . . ?
C3' C4' C11 112.2(3) . . ?
C3' C4' H4' 105.9 . . ?
C5' C4' C11 113.9(3) . . ?
C5' C4' C3' 112.4(3) . . ?
C5' C4' H4' 105.9 . . ?
C4' C5' H5' 116.4 . . ?
C6' C5' C4' 127.1(3) . . ?
C6' C5' H5' 116.4 . . ?
C5' C6' H6' 118.2 . . ?
C5' C6' C7' 123.6(3) . . ?
C7' C6' H6' 118.2 . . ?
O5 C7' C6' 107.0(3) . . ?
O5 C7' C8' 109.5(4) . . ?
O5 C7' C9' 109.6(4) . . ?
C6' C7' C8' 109.1(3) . . ?
C6' C7' C9' 110.6(3) . . ?
C9' C7' C8' 111.0(4) . . ?
C7' C8' H8'A 109.5 . . ?
C7' C8' H8'B 109.5 . . ?
C7' C8' H8'C 109.5 . . ?
H8'A C8' H8'B 109.5 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?
C7' C9' H9'A 109.5 . . ?
C7' C9' H9'B 109.5 . . ?
C7' C9' H9'C 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
C3' C10' H10A 109.5 . . ?
C3' C10' H10B 109.5 . . ?
C3' C10' H10C 109.5 . . ?
H10A C10' H10B 109.5 . . ?
H10A C10' H10C 109.5 . . ?
H10B C10' H10C 109.5 . . ?

_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_cu_22020479_0m
_database_code_depnum_ccdc_archive 'CCDC 2022064'
loop_
_audit_author_name
_audit_author_address
'Cheng-Yu Zheng'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_audit_creation_date             2020-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 O4, 3(H2 O)'
_chemical_formula_sum            'C15 H26 O7'
_chemical_formula_weight         318.36
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   6.7959(2)
_cell_length_b                   10.8224(3)
_cell_length_c                   22.5827(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1660.91(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7367
_cell_measurement_temperature    170
_cell_measurement_theta_max      74.675
_cell_measurement_theta_min      3.915
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1724 before and 0.0815 after correction. The Ratio of minimum to maximum transmission is 0.7125. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14858
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.624
_diffrn_reflns_theta_min         3.915
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                3037
_reflns_number_total             3388
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 1159 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.051
_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)+(0.0715P)²+0.1682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1200
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O7-H7B = O7-H7A
 0.87 with sigma of 0.02
 O1-H1B
 0.87 with sigma of 0.02
3.a Free rotating group:
 O7(H7A), O5(H5A,H5B)
3.b Ternary CH refined with riding coordinates:
 C1(H1), C8(H8), C3(H3), C11(H11)
3.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B), C2(H2A,H2B)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
3.e Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O4 O 0.1193(3) 0.60228(17) 0.48025(8) 0.0249(4) Uani 1 1 d . . . . .
O6 O 0.3664(3) 0.61137(19) 0.23637(8) 0.0279(4) Uani 1 1 d . . . . .
H6 H 0.460788 0.593324 0.213979 0.042 Uiso 1 1 calc GR . . . .
O2 O -0.2079(2) 0.4332(2) 0.46052(9) 0.0326(5) Uani 1 1 d . . . . .
O3 O -0.2633(3) 0.3875(2) 0.55482(9) 0.0337(5) Uani 1 1 d . . . . .
O7 O 0.7262(3) 0.5791(2) 0.17828(10) 0.0371(5) Uani 1 1 d D . . . .
H7A H 0.723871 0.584597 0.139841 0.056 Uiso 1 1 d DG . . . .
O1 O -0.0217(3) 0.2625(2) 0.30156(12) 0.0402(5) Uani 1 1 d D . . . .
O5 O 0.0381(4) 0.4468(3) 0.21877(14) 0.0578(7) Uani 1 1 d . . . . .
H5A H 0.027101 0.388971 0.245256 0.087 Uiso 1 1 d G . . . .
H5B H 0.135146 0.495473 0.228108 0.087 Uiso 1 1 d G . . . .
C12 C -0.1472(4) 0.4053(3) 0.51537(12) 0.0258(5) Uani 1 1 d . . . . .
C7 C 0.1325(3) 0.4741(2) 0.46442(11) 0.0222(5) Uani 1 1 d . . . . .
C5 C 0.3626(3) 0.5341(2) 0.38568(12) 0.0242(5) Uani 1 1 d . . . . .
C1 C 0.2928(4) 0.6651(3) 0.39338(12) 0.0255(5) Uani 1 1 d . . . . .
H1 H 0.389473 0.710350 0.418772 0.031 Uiso 1 1 calc R . . . .
C10 C 0.0905(4) 0.6671(3) 0.42420(12) 0.0271(6) Uani 1 1 d . . . . .
C8 C -0.0410(3) 0.4592(3) 0.42115(12) 0.0266(5) Uani 1 1 d . . . . .
H8 H -0.018623 0.392098 0.391441 0.032 Uiso 1 1 calc R . . . .
C6 C 0.3322(3) 0.4472(3) 0.43650(13) 0.0276(6) Uani 1 1 d . . . . .
H6A H 0.437761 0.458524 0.466204 0.033 Uiso 1 1 calc R . . . .
H6B H 0.336554 0.360692 0.422301 0.033 Uiso 1 1 calc R . . . .
C4 C 0.4387(3) 0.5134(3) 0.33228(12) 0.0259(5) Uani 1 1 d . . . . .
C3 C 0.4383(4) 0.6299(2) 0.29577(12) 0.0261(5) Uani 1 1 d . . . . .
H3 H 0.574290 0.664939 0.294265 0.031 Uiso 1 1 calc R . . . .
C11 C 0.0756(3) 0.3963(3) 0.51746(12) 0.0258(5) Uani 1 1 d . . . . .
H11 H 0.112357 0.308750 0.508519 0.031 Uiso 1 1 calc R . . . .
C9 C -0.0634(4) 0.5856(3) 0.39271(12) 0.0308(6) Uani 1 1 d . . . . .
H9A H -0.197860 0.618400 0.398908 0.037 Uiso 1 1 calc R . . . .
H9B H -0.036887 0.581394 0.349648 0.037 Uiso 1 1 calc R . . . .
C2 C 0.3029(4) 0.7182(3) 0.33002(13) 0.0319(6) Uani 1 1 d . . . . .
H2A H 0.170349 0.720698 0.311870 0.038 Uiso 1 1 calc R . . . .
H2B H 0.358032 0.802853 0.330381 0.038 Uiso 1 1 calc R . . . .
C14 C 0.5249(4) 0.3970(3) 0.30846(15) 0.0370(7) Uani 1 1 d . . . . .
H14A H 0.508316 0.330527 0.337517 0.055 Uiso 1 1 calc GR . . . .
H14B H 0.665411 0.409297 0.300612 0.055 Uiso 1 1 calc GR . . . .
H14C H 0.457847 0.374517 0.271586 0.055 Uiso 1 1 calc GR . . . .
C13 C 0.1668(4) 0.4299(3) 0.57662(13) 0.0385(7) Uani 1 1 d . . . . .
H13A H 0.131769 0.515143 0.586799 0.058 Uiso 1 1 calc GR . . . .
H13B H 0.310248 0.422447 0.574003 0.058 Uiso 1 1 calc GR . . . .
H13C H 0.117261 0.373872 0.607277 0.058 Uiso 1 1 calc GR . . . .
C15 C 0.0229(6) 0.7966(3) 0.43747(16) 0.0452(8) Uani 1 1 d . . . . .
H15A H -0.097103 0.793569 0.461509 0.068 Uiso 1 1 calc GR . . . .
H15B H -0.004457 0.839989 0.400275 0.068 Uiso 1 1 calc GR . . . .
H15C H 0.126046 0.840569 0.459262 0.068 Uiso 1 1 calc GR . . . .
H1A H -0.121(8) 0.220(5) 0.292(2) 0.065(14) Uiso 1 1 d . . . . .
H7B H 0.815(5) 0.532(3) 0.1907(18) 0.040(10) Uiso 1 1 d D . . . .
H1B H 0.076(5) 0.211(3) 0.3054(19) 0.047(11) Uiso 1 1 d 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
O4 C7 1.436(3) . ?
O4 C10 1.460(3) . ?
O6 H6 0.8400 . ?
O6 C3 1.442(3) . ?
O2 C12 1.340(3) . ?
O2 C8 1.468(3) . ?
O3 C12 1.206(3) . ?
O7 H7A 0.8702 . ?
O7 H7B 0.84(2) . ?
O1 H1A 0.85(6) . ?
O1 H1B 0.87(2) . ?
O5 H5A 0.8690 . ?
O5 H5B 0.8700 . ?
C12 C11 1.518(3) . ?
C7 C8 1.540(3) . ?
C7 C6 1.524(3) . ?
C7 C11 1.514(4) . ?
C5 C1 1.506(4) . ?
C5 C6 1.498(4) . ?
C5 C4 1.331(4) . ?
C1 H1 1.0000 . ?
C1 C10 1.541(3) . ?
C1 C2 1.543(4) . ?
C10 C9 1.543(4) . ?
C10 C15 1.505(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.519(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C4 C3 1.506(4) . ?
C4 C14 1.490(4) . ?
C3 H3 1.0000 . ?
C3 C2 1.536(4) . ?
C11 H11 1.0000 . ?
C11 C13 1.517(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C7 O4 C10 104.90(19) . . ?
C3 O6 H6 109.5 . . ?
C12 O2 C8 111.39(18) . . ?
H7A O7 H7B 112.9 . . ?
H1A O1 H1B 107(4) . . ?
H5A O5 H5B 109.5 . . ?
O2 C12 C11 110.5(2) . . ?
O3 C12 O2 121.1(2) . . ?
O3 C12 C11 128.3(3) . . ?
O4 C7 C8 102.2(2) . . ?
O4 C7 C6 110.1(2) . . ?
O4 C7 C11 108.9(2) . . ?
C6 C7 C8 113.5(2) . . ?
C11 C7 C8 104.36(19) . . ?
C11 C7 C6 116.6(2) . . ?
C6 C5 C1 117.3(2) . . ?
C4 C5 C1 112.7(2) . . ?
C4 C5 C6 130.0(2) . . ?
C5 C1 H1 108.7 . . ?
C5 C1 C10 110.3(2) . . ?
C5 C1 C2 103.3(2) . . ?
C10 C1 H1 108.7 . . ?
C10 C1 C2 116.9(2) . . ?
C2 C1 H1 108.7 . . ?
O4 C10 C1 105.4(2) . . ?
O4 C10 C9 102.4(2) . . ?
O4 C10 C15 108.4(2) . . ?
C1 C10 C9 112.9(2) . . ?
C15 C10 C1 112.1(2) . . ?
C15 C10 C9 114.7(3) . . ?
O2 C8 C7 103.15(19) . . ?
O2 C8 H8 112.7 . . ?
O2 C8 C9 110.5(2) . . ?
C7 C8 H8 112.7 . . ?
C9 C8 C7 104.5(2) . . ?
C9 C8 H8 112.7 . . ?
C7 C6 H6A 110.0 . . ?
C7 C6 H6B 110.0 . . ?
C5 C6 C7 108.7(2) . . ?
C5 C6 H6A 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.3 . . ?
C5 C4 C3 110.8(2) . . ?
C5 C4 C14 128.5(3) . . ?
C14 C4 C3 120.7(2) . . ?
O6 C3 C4 113.2(2) . . ?
O6 C3 H3 109.5 . . ?
O6 C3 C2 110.6(2) . . ?
C4 C3 H3 109.5 . . ?
C4 C3 C2 104.3(2) . . ?
C2 C3 H3 109.5 . . ?
C12 C11 H11 107.7 . . ?
C7 C11 C12 101.2(2) . . ?
C7 C11 H11 107.7 . . ?
C7 C11 C13 117.3(2) . . ?
C13 C11 C12 114.8(2) . . ?
C13 C11 H11 107.7 . . ?
C10 C9 H9A 110.8 . . ?
C10 C9 H9B 110.8 . . ?
C8 C9 C10 104.6(2) . . ?
C8 C9 H9A 110.8 . . ?
C8 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
C1 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
C3 C2 C1 105.2(2) . . ?
C3 C2 H2A 110.7 . . ?
C3 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
O6 H6 O7 0.84 1.98 2.797(3) 163.4 . yes
O7 H7A O3 0.87 1.96 2.823(3) 169.8 2_564 yes
O5 H5A O1 0.87 1.90 2.764(4) 174.8 . yes
O5 H5B O6 0.87 2.02 2.882(3) 171.3 . yes
O7 H7B O5 0.84(2) 1.88(2) 2.716(3) 171(4) 1_655 yes
O1 H1B O7 0.87(2) 2.00(3) 2.859(3) 171(4) 3_645 yes

_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_cu_22020154_0m
_database_code_depnum_ccdc_archive 'CCDC 2002637'
loop_
_audit_author_name
_audit_author_address
'Cheng-Yu Zheng'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-05-08 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_audit_creation_date             2020-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H18 O4'
_chemical_formula_sum            'C15 H18 O4'
_chemical_formula_weight         262.29
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.4115(5)
_cell_length_b                   6.9501(5)
_cell_length_c                   15.4228(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.540(4)
_cell_angle_gamma                90
_cell_volume                     675.65(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    298
_cell_measurement_theta_max      74.462
_cell_measurement_theta_min      2.914
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.888
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1410 before and 0.0667 after correction. The Ratio of minimum to maximum transmission is 0.8895. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17282
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.793
_diffrn_reflns_theta_min         2.914
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                2647
_reflns_number_total             2732
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 
;
 Flack x determined using 1173 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2732
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.0743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0807
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C5(H5), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B), C4(H4A,H4B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O2 O 0.59723(19) 0.5097(2) 0.26137(8) 0.0440(3) Uani 1 1 d . . . . .
O3 O 0.4104(3) 0.8384(2) 0.33712(11) 0.0564(4) Uani 1 1 d . . . . .
O4 O 0.6901(3) 0.9188(2) 0.43834(12) 0.0652(4) Uani 1 1 d . . . . .
O1 O -0.1542(3) 0.1034(4) 0.07874(13) 0.0892(7) Uani 1 1 d . . . . .
C11 C 0.5793(3) 0.7947(3) 0.39996(13) 0.0490(5) Uani 1 1 d . . . . .
C6 C 0.2553(3) 0.2546(3) 0.24140(12) 0.0433(4) Uani 1 1 d . . . . .
C7 C 0.3720(3) 0.3048(3) 0.33150(12) 0.0435(4) Uani 1 1 d . . . . .
H7A H 0.482877 0.211005 0.350704 0.052 Uiso 1 1 calc R . . . .
H7B H 0.275348 0.303846 0.373089 0.052 Uiso 1 1 calc R . . . .
C8 C 0.4688(3) 0.5043(3) 0.32826(11) 0.0393(4) Uani 1 1 d . . . . .
C9 C 0.3075(3) 0.6642(3) 0.29819(13) 0.0461(4) Uani 1 1 d . . . . .
H9 H 0.171744 0.640772 0.317003 0.055 Uiso 1 1 calc R . . . .
C5 C 0.3539(3) 0.3156(3) 0.16383(13) 0.0502(5) Uani 1 1 d . . . . .
H5 H 0.470616 0.226925 0.159867 0.060 Uiso 1 1 calc R . . . .
C13 C 0.4471(3) 0.5192(3) 0.17854(12) 0.0485(4) Uani 1 1 d . . . . .
C2 C 0.0657(3) 0.1699(3) 0.21796(13) 0.0486(4) Uani 1 1 d . . . . .
C1 C -0.0740(4) 0.0828(4) 0.27458(16) 0.0605(5) Uani 1 1 d . . . . .
H1A H 0.006698 0.060100 0.332508 0.091 Uiso 1 1 calc GR . . . .
H1B H -0.129792 -0.036897 0.249262 0.091 Uiso 1 1 calc GR . . . .
H1C H -0.188844 0.169058 0.278470 0.091 Uiso 1 1 calc GR . . . .
C10 C 0.5955(3) 0.5805(3) 0.41377(12) 0.0450(4) Uani 1 1 d . . . . .
H10 H 0.516642 0.548607 0.460627 0.054 Uiso 1 1 calc R . . . .
C15 C 0.2846(4) 0.6683(3) 0.19809(14) 0.0552(5) Uani 1 1 d . . . . .
H15A H 0.316557 0.795081 0.177753 0.066 Uiso 1 1 calc R . . . .
H15B H 0.141934 0.632644 0.169915 0.066 Uiso 1 1 calc R . . . .
C12 C 0.8191(4) 0.5053(4) 0.44230(16) 0.0652(6) Uani 1 1 d . . . . .
H12A H 0.897934 0.525170 0.395776 0.098 Uiso 1 1 calc GR . . . .
H12B H 0.814477 0.370367 0.455020 0.098 Uiso 1 1 calc GR . . . .
H12C H 0.886822 0.572839 0.494178 0.098 Uiso 1 1 calc GR . . . .
C14 C 0.5681(4) 0.5796(5) 0.10709(15) 0.0700(7) Uani 1 1 d . . . . .
H14A H 0.636062 0.701133 0.122438 0.105 Uiso 1 1 calc GR . . . .
H14B H 0.471300 0.591510 0.051968 0.105 Uiso 1 1 calc GR . . . .
H14C H 0.673384 0.484364 0.101674 0.105 Uiso 1 1 calc GR . . . .
C4 C 0.1766(4) 0.2787(4) 0.08421(14) 0.0665(6) Uani 1 1 d . . . . .
H4A H 0.121947 0.399038 0.057329 0.080 Uiso 1 1 calc R . . . .
H4B H 0.228124 0.201160 0.040271 0.080 Uiso 1 1 calc R . . . .
C3 C 0.0073(4) 0.1728(4) 0.12125(14) 0.0599(5) Uani 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
O2 C8 1.433(2) . ?
O2 C13 1.454(2) . ?
O3 C11 1.349(3) . ?
O3 C9 1.455(2) . ?
O4 C11 1.203(3) . ?
O1 C3 1.219(3) . ?
C11 C10 1.505(3) . ?
C6 C7 1.494(3) . ?
C6 C5 1.513(3) . ?
C6 C2 1.339(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.523(3) . ?
C8 C9 1.532(2) . ?
C8 C10 1.513(2) . ?
C9 H9 0.9800 . ?
C9 C15 1.524(3) . ?
C5 H5 0.9800 . ?
C5 C13 1.537(3) . ?
C5 C4 1.535(3) . ?
C13 C15 1.538(3) . ?
C13 C14 1.518(3) . ?
C2 C1 1.489(3) . ?
C2 C3 1.470(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C10 H10 0.9800 . ?
C10 C12 1.514(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.507(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
C8 O2 C13 104.99(13) . . ?
C11 O3 C9 110.68(15) . . ?
O3 C11 C10 110.49(17) . . ?
O4 C11 O3 121.1(2) . . ?
O4 C11 C10 128.4(2) . . ?
C7 C6 C5 117.34(17) . . ?
C2 C6 C7 128.99(18) . . ?
C2 C6 C5 113.57(17) . . ?
C6 C7 H7A 110.0 . . ?
C6 C7 H7B 110.0 . . ?
C6 C7 C8 108.65(15) . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
O2 C8 C7 109.81(14) . . ?
O2 C8 C9 102.00(14) . . ?
O2 C8 C10 109.32(14) . . ?
C7 C8 C9 114.45(16) . . ?
C10 C8 C7 116.56(15) . . ?
C10 C8 C9 103.58(15) . . ?
O3 C9 C8 104.39(14) . . ?
O3 C9 H9 112.1 . . ?
O3 C9 C15 110.80(17) . . ?
C8 C9 H9 112.1 . . ?
C15 C9 C8 104.76(15) . . ?
C15 C9 H9 112.1 . . ?
C6 C5 H5 107.9 . . ?
C6 C5 C13 110.43(16) . . ?
C6 C5 C4 103.31(17) . . ?
C13 C5 H5 107.9 . . ?
C4 C5 H5 107.9 . . ?
C4 C5 C13 118.90(19) . . ?
O2 C13 C5 105.36(16) . . ?
O2 C13 C15 102.82(15) . . ?
O2 C13 C14 107.85(17) . . ?
C5 C13 C15 112.94(17) . . ?
C14 C13 C5 112.58(19) . . ?
C14 C13 C15 114.3(2) . . ?
C6 C2 C1 129.33(18) . . ?
C6 C2 C3 108.52(19) . . ?
C3 C2 C1 122.15(18) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C11 C10 C8 102.18(16) . . ?
C11 C10 H10 107.3 . . ?
C11 C10 C12 114.82(19) . . ?
C8 C10 H10 107.3 . . ?
C8 C10 C12 117.48(18) . . ?
C12 C10 H10 107.3 . . ?
C9 C15 C13 104.07(15) . . ?
C9 C15 H15A 110.9 . . ?
C9 C15 H15B 110.9 . . ?
C13 C15 H15A 110.9 . . ?
C13 C15 H15B 110.9 . . ?
H15A C15 H15B 109.0 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
H4A C4 H4B 108.8 . . ?
C3 C4 C5 104.93(17) . . ?
C3 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
O1 C3 C2 125.0(2) . . ?
O1 C3 C4 126.1(2) . . ?
C2 C3 C4 108.91(17) . . ?

_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_cu_22020155_0m
_database_code_depnum_ccdc_archive 'CCDC 2002638'
loop_
_audit_author_name
_audit_author_address
'Cheng-Yu Zheng'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-05-08 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_audit_creation_date             2020-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 O4'
_chemical_formula_sum            'C15 H16 O4'
_chemical_formula_weight         260.28
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   10.4619(19)
_cell_length_b                   10.6895(19)
_cell_length_c                   11.617(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1299.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9110
_cell_measurement_temperature    298
_cell_measurement_theta_max      75.224
_cell_measurement_theta_min      3.826
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_T_max  0.7448
_exptl_absorpt_correction_T_min  0.6466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1539 before and 0.0942 after correction. The Ratio of minimum to maximum transmission is 0.8682. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22909
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.908
_diffrn_reflns_theta_min         5.624
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2524
_reflns_number_total             2651
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 1023 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2651
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.053
_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)+(0.0737P)²+0.1307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1151
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C6(H6A,H6B), C10(H10A,H10B)
2.c X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.27283(15) 0.42452(15) 0.12758(13) 0.0405(4) Uani 1 1 d . . . . .
O2 O 0.54159(16) 0.42655(18) 0.24468(16) 0.0510(4) Uani 1 1 d . . . . .
O4 O 0.0045(2) 0.3412(2) 0.56143(18) 0.0613(6) Uani 1 1 d . . . . .
O1 O 0.6776(2) 0.3656(2) 0.1072(3) 0.0800(7) Uani 1 1 d . . . . .
C14 C 0.2582(2) 0.2240(2) 0.2234(2) 0.0412(5) Uani 1 1 d . . . . .
H14A H 0.212052 0.188122 0.158965 0.049 Uiso 1 1 calc R . . . .
H14B H 0.306310 0.158184 0.261174 0.049 Uiso 1 1 calc R . . . .
C13 C 0.1670(2) 0.2843(2) 0.3066(2) 0.0404(5) Uani 1 1 d . . . . .
C12 C 0.1357(2) 0.2485(2) 0.4138(2) 0.0433(5) Uani 1 1 d . . . . .
C11 C 0.0536(2) 0.3459(2) 0.4661(2) 0.0458(5) Uani 1 1 d . . . . .
C9 C 0.1112(2) 0.4101(2) 0.2732(2) 0.0421(5) Uani 1 1 d . . . . .
H9 H 0.046406 0.396370 0.213573 0.051 Uiso 1 1 calc R . . . .
C4 C 0.3477(2) 0.3281(2) 0.18228(18) 0.0357(4) Uani 1 1 d . . . . .
C5 C 0.4124(2) 0.3960(2) 0.2844(2) 0.0401(5) Uani 1 1 d . . . . .
H5 H 0.414547 0.343049 0.353278 0.048 Uiso 1 1 calc R . . . .
C2 C 0.4578(2) 0.2926(2) 0.1068(2) 0.0432(5) Uani 1 1 d . . . . .
C15 C 0.1719(3) 0.1324(3) 0.4757(3) 0.0562(7) Uani 1 1 d . . . . .
H15A H 0.114641 0.066107 0.454401 0.084 Uiso 1 1 calc GR . . . .
H15B H 0.166766 0.146307 0.557169 0.084 Uiso 1 1 calc GR . . . .
H15C H 0.257775 0.109494 0.455453 0.084 Uiso 1 1 calc GR . . . .
C3 C 0.5719(2) 0.3622(2) 0.1486(3) 0.0513(6) Uani 1 1 d . . . . .
C7 C 0.2172(2) 0.4945(2) 0.2226(2) 0.0419(5) Uani 1 1 d . . . . .
C6 C 0.3320(2) 0.5121(2) 0.3037(2) 0.0473(6) Uani 1 1 d . . . . .
H6A H 0.379512 0.587018 0.284071 0.057 Uiso 1 1 calc R . . . .
H6B H 0.304339 0.517730 0.383196 0.057 Uiso 1 1 calc R . . . .
C10 C 0.0435(3) 0.4542(3) 0.3831(2) 0.0513(6) Uani 1 1 d . . . . .
H10A H 0.085078 0.527945 0.414256 0.062 Uiso 1 1 calc R . . . .
H10B H -0.045310 0.474033 0.367476 0.062 Uiso 1 1 calc R . . . .
C1 C 0.4615(3) 0.2123(3) 0.0211(2) 0.0569(7) Uani 1 1 d . . . . .
H1A H 0.538304 0.196550 -0.016597 0.068 Uiso 1 1 calc R . . . .
H1B H 0.387430 0.171153 -0.001797 0.068 Uiso 1 1 calc R . . . .
C8 C 0.1637(3) 0.6154(3) 0.1744(3) 0.0644(8) Uani 1 1 d . . . . .
H8A H 0.232168 0.664877 0.143480 0.097 Uiso 1 1 calc GR . . . .
H8B H 0.121717 0.661079 0.234610 0.097 Uiso 1 1 calc GR . . . .
H8C H 0.103466 0.596701 0.114478 0.097 Uiso 1 1 calc GR . . . .


_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 C4 1.442(3) . ?
O3 C7 1.455(3) . ?
O2 C5 1.465(3) . ?
O2 C3 1.348(4) . ?
O4 C11 1.222(3) . ?
O1 C3 1.207(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.503(3) . ?
C14 C4 1.531(3) . ?
C13 C12 1.344(3) . ?
C13 C9 1.516(3) . ?
C12 C11 1.480(3) . ?
C12 C15 1.483(4) . ?
C11 C10 1.511(4) . ?
C9 H9 0.9800 . ?
C9 C7 1.546(3) . ?
C9 C10 1.535(3) . ?
C4 C5 1.547(3) . ?
C4 C2 1.496(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.515(3) . ?
C2 C3 1.488(4) . ?
C2 C1 1.315(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C7 C6 1.538(3) . ?
C7 C8 1.515(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C1 H1A 0.9300 . ?
C1 H1B 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O3 C7 104.50(15) . . ?
C3 O2 C5 111.33(19) . . ?
H14A C14 H14B 108.7 . . ?
C13 C14 H14A 110.5 . . ?
C13 C14 H14B 110.5 . . ?
C13 C14 C4 106.10(17) . . ?
C4 C14 H14A 110.5 . . ?
C4 C14 H14B 110.5 . . ?
C14 C13 C9 117.4(2) . . ?
C12 C13 C14 128.9(2) . . ?
C12 C13 C9 113.36(19) . . ?
C13 C12 C11 108.7(2) . . ?
C13 C12 C15 128.7(2) . . ?
C11 C12 C15 122.5(2) . . ?
O4 C11 C12 126.0(2) . . ?
O4 C11 C10 125.5(2) . . ?
C12 C11 C10 108.5(2) . . ?
C13 C9 H9 108.4 . . ?
C13 C9 C7 109.80(18) . . ?
C13 C9 C10 103.74(19) . . ?
C7 C9 H9 108.4 . . ?
C10 C9 H9 108.4 . . ?
C10 C9 C7 117.9(2) . . ?
O3 C4 C14 108.95(18) . . ?
O3 C4 C5 103.89(16) . . ?
O3 C4 C2 109.91(17) . . ?
C14 C4 C5 111.66(18) . . ?
C2 C4 C14 118.05(18) . . ?
C2 C4 C5 103.40(18) . . ?
O2 C5 C4 105.46(18) . . ?
O2 C5 H5 111.4 . . ?
O2 C5 C6 112.08(19) . . ?
C4 C5 H5 111.4 . . ?
C6 C5 C4 104.74(17) . . ?
C6 C5 H5 111.4 . . ?
C3 C2 C4 107.4(2) . . ?
C1 C2 C4 129.2(2) . . ?
C1 C2 C3 123.4(2) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C3 C2 109.7(2) . . ?
O1 C3 O2 122.0(3) . . ?
O1 C3 C2 128.3(3) . . ?
O3 C7 C9 105.98(18) . . ?
O3 C7 C6 102.39(17) . . ?
O3 C7 C8 107.76(19) . . ?
C6 C7 C9 113.53(19) . . ?
C8 C7 C9 112.0(2) . . ?
C8 C7 C6 114.2(2) . . ?
C5 C6 C7 104.09(18) . . ?
C5 C6 H6A 110.9 . . ?
C5 C6 H6B 110.9 . . ?
C7 C6 H6A 110.9 . . ?
C7 C6 H6B 110.9 . . ?
H6A C6 H6B 109.0 . . ?
C11 C10 C9 105.24(19) . . ?
C11 C10 H10A 110.7 . . ?
C11 C10 H10B 110.7 . . ?
C9 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_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_cu_22020436_0m
_database_code_depnum_ccdc_archive 'CCDC 2022065'
loop_
_audit_author_name
_audit_author_address
'Cheng-Yu Zheng'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_audit_creation_date             2020-07-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 O4'
_chemical_formula_sum            'C15 H20 O4'
_chemical_formula_weight         264.31
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   13.0969(2)
_cell_length_b                   13.0969(2)
_cell_length_c                   8.2344(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1412.44(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.289
_cell_measurement_theta_min      4.775
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1332 before and 0.0626 after correction. The Ratio of minimum to maximum transmission is 0.7456. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17538
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.281
_diffrn_reflns_theta_min         3.374
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                2698
_reflns_number_total             2714
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 1217 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2714
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.069
_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)+(0.0406P)²+0.1790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0716
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C1(H1A), C11(H11), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B), C2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O2 O 0.52731(8) 0.15605(8) 0.50762(14) 0.0239(3) Uani 1 1 d . . . . .
O3 O 0.48983(9) 0.36846(9) 0.41229(15) 0.0294(3) Uani 1 1 d . . . . .
O1 O 0.93110(10) 0.06157(10) 0.65761(17) 0.0355(3) Uani 1 1 d . . . . .
O4 O 0.34817(11) 0.34178(12) 0.2685(2) 0.0429(4) Uani 1 1 d . . . . .
C7 C 0.57167(12) 0.20967(12) 0.37240(19) 0.0216(3) Uani 1 1 d . . . . .
C6 C 0.67124(12) 0.15784(12) 0.3217(2) 0.0235(3) Uani 1 1 d . . . . .
H6A H 0.657138 0.088268 0.280353 0.028 Uiso 1 1 calc R . . . .
H6B H 0.704723 0.197520 0.234274 0.028 Uiso 1 1 calc R . . . .
C8 C 0.58699(12) 0.31729(12) 0.4420(2) 0.0243(3) Uani 1 1 d . . . . .
H8 H 0.645529 0.353696 0.389719 0.029 Uiso 1 1 calc R . . . .
C5 C 0.73959(12) 0.15248(12) 0.46801(19) 0.0231(3) Uani 1 1 d . . . . .
C12 C 0.43308(14) 0.31562(14) 0.3044(2) 0.0296(4) Uani 1 1 d . . . . .
C1 C 0.69061(12) 0.12599(12) 0.6283(2) 0.0242(3) Uani 1 1 d . . . . .
H1A H 0.675675 0.051118 0.630007 0.029 Uiso 1 1 calc R . . . .
C9 C 0.60359(13) 0.30130(12) 0.6232(2) 0.0265(3) Uani 1 1 d . . . . .
H9A H 0.552860 0.340120 0.687530 0.032 Uiso 1 1 calc R . . . .
H9B H 0.673067 0.322914 0.655852 0.032 Uiso 1 1 calc R . . . .
C11 C 0.49166(12) 0.22443(13) 0.2415(2) 0.0248(3) Uani 1 1 d . . . . .
H11 H 0.527682 0.245871 0.139980 0.030 Uiso 1 1 calc R . . . .
C10 C 0.58939(12) 0.18485(12) 0.6470(2) 0.0244(3) Uani 1 1 d . . . . .
C4 C 0.83905(12) 0.17281(12) 0.4815(2) 0.0270(4) Uani 1 1 d . . . . .
C2 C 0.77525(14) 0.14872(14) 0.7532(2) 0.0311(4) Uani 1 1 d . . . . .
H2A H 0.761658 0.213901 0.810127 0.037 Uiso 1 1 calc R . . . .
H2B H 0.779727 0.093305 0.834672 0.037 Uiso 1 1 calc R . . . .
C3 C 0.87446(13) 0.15560(13) 0.6539(2) 0.0296(4) Uani 1 1 d . . . . .
H3 H 0.917610 0.213838 0.692113 0.036 Uiso 1 1 calc R . . . .
C13 C 0.42499(14) 0.13348(15) 0.2000(2) 0.0329(4) Uani 1 1 d . . . . .
H13A H 0.467084 0.079596 0.151679 0.049 Uiso 1 1 calc GR . . . .
H13B H 0.372218 0.154394 0.122495 0.049 Uiso 1 1 calc GR . . . .
H13C H 0.392577 0.107648 0.299114 0.049 Uiso 1 1 calc GR . . . .
C15 C 0.53151(14) 0.15642(14) 0.7994(2) 0.0328(4) Uani 1 1 d . . . . .
H15A H 0.464613 0.189928 0.798764 0.049 Uiso 1 1 calc GR . . . .
H15B H 0.570215 0.178691 0.894892 0.049 Uiso 1 1 calc GR . . . .
H15C H 0.522225 0.082207 0.803267 0.049 Uiso 1 1 calc GR . . . .
C14 C 0.91288(15) 0.20176(16) 0.3509(3) 0.0392(4) Uani 1 1 d . . . . .
H14A H 0.879575 0.195672 0.244728 0.059 Uiso 1 1 calc GR . . . .
H14B H 0.972160 0.156171 0.354904 0.059 Uiso 1 1 calc GR . . . .
H14C H 0.935272 0.272400 0.367327 0.059 Uiso 1 1 calc GR . . . .
H1 H 0.970(2) 0.0609(19) 0.744(4) 0.049(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
O2 C7 1.4389(19) . ?
O2 C10 1.4559(19) . ?
O3 C8 1.459(2) . ?
O3 C12 1.349(2) . ?
O1 C3 1.438(2) . ?
O4 C12 1.201(2) . ?
C7 C6 1.528(2) . ?
C7 C8 1.535(2) . ?
C7 C11 1.516(2) . ?
C6 C5 1.503(2) . ?
C8 C9 1.523(2) . ?
C5 C1 1.508(2) . ?
C5 C4 1.334(2) . ?
C12 C11 1.511(2) . ?
C1 C10 1.541(2) . ?
C1 C2 1.541(2) . ?
C9 C10 1.549(2) . ?
C11 C13 1.516(2) . ?
C10 C15 1.513(2) . ?
C4 C3 1.510(3) . ?
C4 C14 1.495(3) . ?
C2 C3 1.538(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
C7 O2 C10 104.94(11) . . ?
C12 O3 C8 110.80(12) . . ?
O2 C7 C6 109.83(13) . . ?
O2 C7 C8 102.26(12) . . ?
O2 C7 C11 109.48(13) . . ?
C6 C7 C8 113.47(13) . . ?
C11 C7 C6 116.87(14) . . ?
C11 C7 C8 103.81(13) . . ?
C5 C6 C7 108.04(13) . . ?
O3 C8 C7 104.20(13) . . ?
O3 C8 C9 110.59(13) . . ?
C9 C8 C7 104.96(13) . . ?
C6 C5 C1 117.35(13) . . ?
C4 C5 C6 129.73(16) . . ?
C4 C5 C1 112.83(15) . . ?
O3 C12 C11 110.58(14) . . ?
O4 C12 O3 121.72(17) . . ?
O4 C12 C11 127.70(18) . . ?
C5 C1 C10 109.75(13) . . ?
C5 C1 C2 103.52(13) . . ?
C2 C1 C10 117.11(14) . . ?
C8 C9 C10 103.99(13) . . ?
C7 C11 C13 117.27(14) . . ?
C12 C11 C7 102.00(14) . . ?
C12 C11 C13 113.94(14) . . ?
O2 C10 C1 105.80(12) . . ?
O2 C10 C9 102.88(13) . . ?
O2 C10 C15 108.07(13) . . ?
C1 C10 C9 112.13(13) . . ?
C15 C10 C1 112.98(14) . . ?
C15 C10 C9 114.03(14) . . ?
C5 C4 C3 110.39(15) . . ?
C5 C4 C14 128.44(17) . . ?
C14 C4 C3 121.04(15) . . ?
C3 C2 C1 105.33(14) . . ?
O1 C3 C4 107.81(14) . . ?
O1 C3 C2 112.00(15) . . ?
C4 C3 C2 104.42(14) . . ?

_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_mj20335_0m
_database_code_depnum_ccdc_archive 'CCDC 2013505'
loop_
_audit_author_name
_audit_author_address
'Cheng-Yu Zheng '
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-07-02 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_audit_creation_date             2020-07-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H30 O6, 0.5(H2 O)'
_chemical_formula_sum            'C25 H31 O6.50'
_chemical_formula_weight         435.50
_chemical_absolute_configuration rmad
_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 0.0148 0.0070 '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 0.0412 0.0250 '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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.2867(14)
_cell_length_b                   21.497(3)
_cell_length_c                   9.6289(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2543.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.89
_cell_measurement_theta_min      5.37
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.429
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1372 before and 0.0544 after correction. The Ratio of minimum to maximum transmission is 0.8597. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             932
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            27725
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.865
_diffrn_reflns_theta_min         3.605
_diffrn_ambient_temperature      172.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4723
_reflns_number_total             4808
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 2022 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4808
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.086
_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)+(0.0406P)²+0.2961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0733
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H7A(0.5) H7B(0.5)
3.a Riding coordinates:
 O7(H7A,H7B)
3.b Ternary CH refined with riding coordinates:
 C1(H1), C8(H8)
3.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C9(H9A,H9B), C13(H13A,H13B), C1'(H1'A,H1'B)
3.d Aromatic/amide H refined with riding coordinates:
 C5'(H5'), C6'(H6')
3.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C8'(H8'A,H8'B,H8'C), C9'(H9'A,H9'B,
 H9'C), C10'(H10A,H10B,H10C)
3.f Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.40429(10) 0.20384(5) -0.07321(12) 0.0324(3) Uani 1 1 d . . . . .
O2 O 0.68733(8) 0.10633(4) 0.36060(10) 0.0210(2) Uani 1 1 d . . . . .
O3 O 0.89179(9) 0.17174(5) 0.27362(12) 0.0272(2) Uani 1 1 d . . . . .
O4 O 0.99146(9) 0.16991(6) 0.46681(14) 0.0353(3) Uani 1 1 d . . . . .
O5 O 0.65085(13) 0.21826(7) 0.86871(14) 0.0486(4) Uani 1 1 d . . . . .
O6 O 0.92285(9) 0.38817(5) 0.28063(12) 0.0290(3) Uani 1 1 d . . . . .
H6 H 0.914413 0.359587 0.222133 0.044 Uiso 1 1 calc GR . . . .
C1 C 0.54014(12) 0.12295(7) 0.20371(15) 0.0217(3) Uani 1 1 d . . . . .
H1 H 0.490843 0.102051 0.271913 0.026 Uiso 1 1 calc R . . . .
C2 C 0.48749(14) 0.12032(7) 0.05974(16) 0.0258(3) Uani 1 1 d . . . . .
H2A H 0.539493 0.104209 -0.010063 0.031 Uiso 1 1 calc R . . . .
H2B H 0.422283 0.093270 0.060728 0.031 Uiso 1 1 calc R . . . .
C3 C 0.45655(12) 0.18707(7) 0.02775(16) 0.0234(3) Uani 1 1 d . . . . .
C4 C 0.50034(12) 0.22737(7) 0.13846(15) 0.0220(3) Uani 1 1 d . . . . .
C5 C 0.54484(11) 0.19164(6) 0.23709(15) 0.0203(3) Uani 1 1 d . . . . .
C6 C 0.60659(12) 0.20918(7) 0.36560(15) 0.0214(3) Uani 1 1 d . . . . .
H6A H 0.562858 0.199572 0.449251 0.026 Uiso 1 1 calc R . . . .
H6B H 0.622737 0.254299 0.365176 0.026 Uiso 1 1 calc R . . . .
C7 C 0.71293(12) 0.17163(6) 0.36711(15) 0.0191(3) Uani 1 1 d . . . . .
C8 C 0.77941(12) 0.18198(7) 0.23352(16) 0.0219(3) Uani 1 1 d . . . . .
H8 H 0.768066 0.224611 0.194581 0.026 Uiso 1 1 calc R . . . .
C9 C 0.74038(13) 0.13143(7) 0.13354(16) 0.0249(3) Uani 1 1 d . . . . .
H9A H 0.801272 0.103988 0.105585 0.030 Uiso 1 1 calc R . . . .
H9B H 0.707548 0.149974 0.049273 0.030 Uiso 1 1 calc R . . . .
C10 C 0.65478(13) 0.09516(6) 0.21791(16) 0.0222(3) Uani 1 1 d . . . . .
C11 C 0.79458(12) 0.18211(6) 0.48730(15) 0.0213(3) Uani 1 1 d . . . . .
C12 C 0.90411(13) 0.17438(7) 0.41221(17) 0.0246(3) Uani 1 1 d . . . . .
C13 C 0.78998(14) 0.13311(7) 0.60306(17) 0.0284(4) Uani 1 1 d . . . . .
H13A H 0.785652 0.091129 0.561157 0.034 Uiso 1 1 calc R . . . .
H13B H 0.857522 0.135261 0.658917 0.034 Uiso 1 1 calc R . . . .
C14 C 0.49403(15) 0.29653(7) 0.12633(18) 0.0313(4) Uani 1 1 d . . . . .
H14A H 0.520343 0.315611 0.212451 0.047 Uiso 1 1 calc GR . . . .
H14B H 0.418356 0.308972 0.110141 0.047 Uiso 1 1 calc GR . . . .
H14C H 0.539267 0.310401 0.048426 0.047 Uiso 1 1 calc GR . . . .
C15 C 0.65495(15) 0.02563(7) 0.19283(18) 0.0318(4) Uani 1 1 d . . . . .
H15A H 0.728586 0.009272 0.206898 0.048 Uiso 1 1 calc GR . . . .
H15B H 0.631573 0.017120 0.097391 0.048 Uiso 1 1 calc GR . . . .
H15C H 0.604814 0.005478 0.257957 0.048 Uiso 1 1 calc GR . . . .
C1' C 0.69297(15) 0.14322(8) 0.69644(18) 0.0339(4) Uani 1 1 d . . . . .
H1'A H 0.625338 0.136102 0.642865 0.041 Uiso 1 1 calc R . . . .
H1'B H 0.694994 0.112666 0.773327 0.041 Uiso 1 1 calc R . . . .
C2' C 0.69148(13) 0.20774(8) 0.75550(17) 0.0317(4) Uani 1 1 d . . . . .
C3' C 0.74033(12) 0.25921(7) 0.67295(16) 0.0244(3) Uani 1 1 d . . . . .
C4' C 0.78548(12) 0.24809(7) 0.54658(15) 0.0206(3) Uani 1 1 d . . . . .
C5' C 0.82837(12) 0.29801(7) 0.45624(15) 0.0220(3) Uani 1 1 d . . . . .
H5' H 0.897246 0.291567 0.413782 0.026 Uiso 1 1 calc R . . . .
C6' C 0.77733(13) 0.35126(7) 0.43026(16) 0.0254(3) Uani 1 1 d . . . . .
H6' H 0.707761 0.356938 0.471399 0.030 Uiso 1 1 calc R . . . .
C7' C 0.82031(14) 0.40348(7) 0.34109(17) 0.0281(3) Uani 1 1 d . . . . .
C8' C 0.73843(18) 0.41856(11) 0.2273(2) 0.0498(5) Uani 1 1 d . . . . .
H8'A H 0.764589 0.454091 0.173022 0.075 Uiso 1 1 calc GR . . . .
H8'B H 0.668104 0.428891 0.269457 0.075 Uiso 1 1 calc GR . . . .
H8'C H 0.729883 0.382399 0.166328 0.075 Uiso 1 1 calc GR . . . .
C9' C 0.8421(2) 0.45960(8) 0.4343(2) 0.0466(5) Uani 1 1 d . . . . .
H9'A H 0.902979 0.450309 0.496735 0.070 Uiso 1 1 calc GR . . . .
H9'B H 0.776946 0.468798 0.489272 0.070 Uiso 1 1 calc GR . . . .
H9'C H 0.860425 0.495705 0.376722 0.070 Uiso 1 1 calc GR . . . .
C10' C 0.73228(15) 0.32183(8) 0.74102(18) 0.0327(4) Uani 1 1 d . . . . .
H10A H 0.786781 0.349823 0.700832 0.049 Uiso 1 1 calc GR . . . .
H10B H 0.745396 0.317524 0.840954 0.049 Uiso 1 1 calc GR . . . .
H10C H 0.659393 0.339038 0.725747 0.049 Uiso 1 1 calc GR . . . .
O7 O 1.000000 0.500000 0.1376(2) 0.0640(7) Uani 1 2 d S T P . .
H7A H 1.032100 0.525350 0.194756 0.096 Uiso 0.5 1 d R . . . .
H7B H 0.995300 0.465170 0.183126 0.096 Uiso 0.5 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.2195(19) . ?
O2 C7 1.4400(16) . ?
O2 C10 1.4510(18) . ?
O3 C8 1.4505(19) . ?
O3 C12 1.344(2) . ?
O4 C12 1.199(2) . ?
O5 C2' 1.220(2) . ?
O6 H6 0.8400 . ?
O6 C7' 1.426(2) . ?
C1 H1 1.0000 . ?
C1 C2 1.531(2) . ?
C1 C5 1.5123(19) . ?
C1 C10 1.536(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.516(2) . ?
C3 C4 1.475(2) . ?
C4 C5 1.338(2) . ?
C4 C14 1.493(2) . ?
C5 C6 1.500(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.536(2) . ?
C7 C8 1.540(2) . ?
C7 C11 1.548(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.529(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.541(2) . ?
C10 C15 1.514(2) . ?
C11 C12 1.537(2) . ?
C11 C13 1.535(2) . ?
C11 C4' 1.533(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C1' 1.509(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C1' H1'A 0.9900 . ?
C1' H1'B 0.9900 . ?
C1' C2' 1.499(3) . ?
C2' C3' 1.489(2) . ?
C3' C4' 1.359(2) . ?
C3' C10' 1.501(2) . ?
C4' C5' 1.478(2) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.329(2) . ?
C6' H6' 0.9500 . ?
C6' C7' 1.509(2) . ?
C7' C8' 1.522(3) . ?
C7' C9' 1.527(2) . ?
C8' H8'A 0.9800 . ?
C8' H8'B 0.9800 . ?
C8' H8'C 0.9800 . ?
C9' H9'A 0.9800 . ?
C9' H9'B 0.9800 . ?
C9' H9'C 0.9800 . ?
C10' H10A 0.9800 . ?
C10' H10B 0.9800 . ?
C10' H10C 0.9800 . ?
O7 H7A 0.8693 2_765 ?
O7 H7A 0.8693 . ?
O7 H7B 0.8697 2_765 ?
O7 H7B 0.8697 . ?

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
C7 O2 C10 105.23(10) . . ?
C12 O3 C8 111.41(12) . . ?
C7' O6 H6 109.5 . . ?
C2 C1 H1 108.8 . . ?
C2 C1 C10 116.99(13) . . ?
C5 C1 H1 108.8 . . ?
C5 C1 C2 104.16(12) . . ?
C5 C1 C10 109.01(11) . . ?
C10 C1 H1 108.8 . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 C1 104.78(12) . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
O1 C3 C2 125.02(14) . . ?
O1 C3 C4 126.47(14) . . ?
C4 C3 C2 108.51(13) . . ?
C3 C4 C14 120.61(13) . . ?
C5 C4 C3 108.95(13) . . ?
C5 C4 C14 130.40(14) . . ?
C4 C5 C1 113.20(13) . . ?
C4 C5 C6 130.39(13) . . ?
C6 C5 C1 116.12(12) . . ?
C5 C6 H6A 110.1 . . ?
C5 C6 H6B 110.1 . . ?
C5 C6 C7 107.82(11) . . ?
H6A C6 H6B 108.5 . . ?
C7 C6 H6A 110.1 . . ?
C7 C6 H6B 110.1 . . ?
O2 C7 C6 109.03(11) . . ?
O2 C7 C8 102.72(11) . . ?
O2 C7 C11 108.42(11) . . ?
C6 C7 C8 111.56(12) . . ?
C6 C7 C11 118.81(12) . . ?
C8 C7 C11 105.05(11) . . ?
O3 C8 C7 105.11(12) . . ?
O3 C8 H8 111.8 . . ?
O3 C8 C9 111.00(12) . . ?
C7 C8 H8 111.8 . . ?
C9 C8 C7 104.89(11) . . ?
C9 C8 H8 111.8 . . ?
C8 C9 H9A 111.0 . . ?
C8 C9 H9B 111.0 . . ?
C8 C9 C10 103.99(12) . . ?
H9A C9 H9B 109.0 . . ?
C10 C9 H9A 111.0 . . ?
C10 C9 H9B 111.0 . . ?
O2 C10 C1 105.82(12) . . ?
O2 C10 C9 103.15(11) . . ?
O2 C10 C15 108.30(12) . . ?
C1 C10 C9 112.47(12) . . ?
C15 C10 C1 111.77(13) . . ?
C15 C10 C9 114.49(14) . . ?
C12 C11 C7 101.54(12) . . ?
C13 C11 C7 114.78(12) . . ?
C13 C11 C12 107.45(12) . . ?
C4' C11 C7 111.45(11) . . ?
C4' C11 C12 109.82(11) . . ?
C4' C11 C13 111.22(12) . . ?
O3 C12 C11 111.90(13) . . ?
O4 C12 O3 122.19(15) . . ?
O4 C12 C11 125.89(15) . . ?
C11 C13 H13A 109.4 . . ?
C11 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C1' C13 C11 111.29(13) . . ?
C1' C13 H13A 109.4 . . ?
C1' C13 H13B 109.4 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C1' H1'A 109.3 . . ?
C13 C1' H1'B 109.3 . . ?
H1'A C1' H1'B 108.0 . . ?
C2' C1' C13 111.65(13) . . ?
C2' C1' H1'A 109.3 . . ?
C2' C1' H1'B 109.3 . . ?
O5 C2' C1' 121.02(16) . . ?
O5 C2' C3' 120.29(17) . . ?
C3' C2' C1' 118.69(14) . . ?
C2' C3' C10' 114.01(14) . . ?
C4' C3' C2' 120.80(14) . . ?
C4' C3' C10' 125.17(15) . . ?
C3' C4' C11 121.74(13) . . ?
C3' C4' C5' 123.01(13) . . ?
C5' C4' C11 115.25(12) . . ?
C4' C5' H5' 117.7 . . ?
C6' C5' C4' 124.60(14) . . ?
C6' C5' H5' 117.7 . . ?
C5' C6' H6' 117.2 . . ?
C5' C6' C7' 125.65(15) . . ?
C7' C6' H6' 117.2 . . ?
O6 C7' C6' 111.71(13) . . ?
O6 C7' C8' 109.83(15) . . ?
O6 C7' C9' 105.49(14) . . ?
C6' C7' C8' 109.67(15) . . ?
C6' C7' C9' 108.34(14) . . ?
C8' C7' C9' 111.75(16) . . ?
C7' C8' H8'A 109.5 . . ?
C7' C8' H8'B 109.5 . . ?
C7' C8' H8'C 109.5 . . ?
H8'A C8' H8'B 109.5 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?
C7' C9' H9'A 109.5 . . ?
C7' C9' H9'B 109.5 . . ?
C7' C9' H9'C 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
C3' C10' H10A 109.5 . . ?
C3' C10' H10B 109.5 . . ?
C3' C10' H10C 109.5 . . ?
H10A C10' H10B 109.5 . . ?
H10A C10' H10C 109.5 . . ?
H10B C10' H10C 109.5 . . ?
H7A O7 H7A 101.4 . 2_765 ?
H7A O7 H7B 27.2 . 2_765 ?
H7A O7 H7B 104.5 2_765 2_765 ?
H7A O7 H7B 104.5 . . ?
H7B O7 H7A 27.2 . 2_765 ?
H7B O7 H7B 119.4 . 2_765 ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.133 229.0 50.0 ?
2 0.500 0.500 -0.885 229.0 50.0 ?

_platon_squeeze_void_probe_radius 1.20
_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_cu_2022538_0m
_database_code_depnum_ccdc_archive 'CCDC 2181591'
loop_
_audit_author_name
_audit_author_address
'Yao-Yue Fan'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-06-24 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_audit_creation_date             2022-06-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H32 O5'
_chemical_formula_sum            'C25 H32 O5'
_chemical_formula_weight         412.50
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   6.9481(2)
_cell_length_b                   15.6259(4)
_cell_length_c                   20.1605(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2188.83(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9670
_cell_measurement_temperature    150
_cell_measurement_theta_max      79.73
_cell_measurement_theta_min      5.22
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.922
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1653 before and 0.0901 after correction. The Ratio of minimum to maximum transmission is 0.9023. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            38753
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.023
_diffrn_reflns_theta_min         3.579
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                4439
_reflns_number_total             4706
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1798 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4706
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.049
_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)+(0.0330P)²+0.4895P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0763
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C4'(H4'), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C6(H6A,H6B), C9(H9A,H9B), C1'(H1'A,H1'B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C5'(H5'), C6'(H6'), C2'(H2')
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C10'(H10A,H10B,H10C), C9'(H9'A,H9'B,H9'C), C8'(H8'A,H8'B,
 H8'C), C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.29269(18) 0.61026(7) 0.25890(6) 0.0196(3) Uani 1 1 d . . . . .
O4 O -0.07817(18) 0.73936(9) 0.15060(7) 0.0262(3) Uani 1 1 d . . . . .
O2 O 0.00780(18) 0.75077(9) 0.25632(6) 0.0256(3) Uani 1 1 d . . . . .
O5 O 0.6858(2) 0.40578(8) 0.12258(7) 0.0293(3) Uani 1 1 d . . . . .
H5 H 0.724091 0.391935 0.084541 0.044 Uiso 1 1 calc GR . . . .
O1 O 0.7090(2) 0.68567(10) 0.50515(7) 0.0376(4) Uani 1 1 d . . . . .
C12 C 0.0478(2) 0.73908(11) 0.19131(9) 0.0200(3) Uani 1 1 d . . . . .
C5' C 0.5022(2) 0.62355(11) 0.12574(8) 0.0177(3) Uani 1 1 d . . . . .
H5' H 0.610536 0.659995 0.120378 0.021 Uiso 1 1 calc R . . . .
C6' C 0.5320(3) 0.54075(12) 0.13452(9) 0.0207(4) Uani 1 1 d . . . . .
H6' H 0.421502 0.506298 0.142113 0.025 Uiso 1 1 calc R . . . .
C3' C 0.2727(3) 0.70240(12) 0.05536(8) 0.0208(3) Uani 1 1 d . . . . .
C8 C 0.1795(2) 0.74132(12) 0.29688(9) 0.0211(4) Uani 1 1 d . . . . .
H8 H 0.224838 0.797188 0.315356 0.025 Uiso 1 1 calc R . . . .
C11 C 0.2652(2) 0.72787(10) 0.18058(8) 0.0167(3) Uani 1 1 d . . . . .
C7 C 0.3288(2) 0.70026(10) 0.25036(8) 0.0171(3) Uani 1 1 d . . . . .
C4' C 0.3030(2) 0.66288(11) 0.12386(8) 0.0171(3) Uani 1 1 d . . . . .
H4' H 0.207804 0.615317 0.128850 0.021 Uiso 1 1 calc R . . . .
C5 C 0.5644(2) 0.69026(12) 0.34113(9) 0.0203(4) Uani 1 1 d . . . . .
C13 C 0.3521(3) 0.81580(11) 0.16268(9) 0.0217(4) Uani 1 1 d . . . . .
H13A H 0.328379 0.856358 0.199506 0.026 Uiso 1 1 calc R . . . .
H13B H 0.493111 0.809851 0.157276 0.026 Uiso 1 1 calc R . . . .
C6 C 0.5359(2) 0.72126(12) 0.27167(9) 0.0208(4) Uani 1 1 d . . . . .
H6A H 0.628639 0.692815 0.241600 0.025 Uiso 1 1 calc R . . . .
H6B H 0.557879 0.783798 0.269442 0.025 Uiso 1 1 calc R . . . .
C3 C 0.6316(3) 0.67419(13) 0.45151(9) 0.0269(4) Uani 1 1 d . . . . .
C7' C 0.7242(3) 0.49535(12) 0.13370(9) 0.0223(4) Uani 1 1 d . . . . .
C10 C 0.2723(3) 0.59841(12) 0.32996(8) 0.0228(4) Uani 1 1 d . . . . .
C9 C 0.1464(3) 0.67443(13) 0.35093(9) 0.0257(4) Uani 1 1 d . . . . .
H9A H 0.009067 0.657699 0.353023 0.031 Uiso 1 1 calc R . . . .
H9B H 0.186333 0.696548 0.394831 0.031 Uiso 1 1 calc R . . . .
C4 C 0.6495(3) 0.72933(12) 0.39276(9) 0.0225(4) Uani 1 1 d . . . . .
C1' C 0.2662(3) 0.85204(12) 0.09889(10) 0.0272(4) Uani 1 1 d . . . . .
H1'A H 0.134359 0.873091 0.107873 0.033 Uiso 1 1 calc R . . . .
H1'B H 0.344742 0.901189 0.083801 0.033 Uiso 1 1 calc R . . . .
C14 C 0.7518(3) 0.81330(13) 0.39569(9) 0.0275(4) Uani 1 1 d . . . . .
H14A H 0.767290 0.835977 0.350681 0.041 Uiso 1 1 calc GR . . . .
H14B H 0.878707 0.805340 0.415971 0.041 Uiso 1 1 calc GR . . . .
H14C H 0.676506 0.853692 0.422331 0.041 Uiso 1 1 calc GR . . . .
C2' C 0.2591(3) 0.78597(12) 0.04519(9) 0.0256(4) Uani 1 1 d . . . . .
H2' H 0.243818 0.805241 0.000810 0.031 Uiso 1 1 calc R . . . .
C1 C 0.4774(3) 0.60465(12) 0.35879(9) 0.0231(4) Uani 1 1 d . . . . .
H1 H 0.557840 0.558656 0.338287 0.028 Uiso 1 1 calc R . . . .
C10' C 0.2639(3) 0.63979(13) -0.00136(9) 0.0266(4) Uani 1 1 d . . . . .
H10A H 0.380041 0.604186 -0.001226 0.040 Uiso 1 1 calc GR . . . .
H10B H 0.255857 0.671157 -0.043358 0.040 Uiso 1 1 calc GR . . . .
H10C H 0.150151 0.603274 0.003607 0.040 Uiso 1 1 calc GR . . . .
C9' C 0.8564(3) 0.52967(12) 0.07997(10) 0.0263(4) Uani 1 1 d . . . . .
H9'A H 0.976480 0.496780 0.079722 0.039 Uiso 1 1 calc GR . . . .
H9'B H 0.884934 0.590031 0.088767 0.039 Uiso 1 1 calc GR . . . .
H9'C H 0.793070 0.524362 0.036727 0.039 Uiso 1 1 calc GR . . . .
C2 C 0.5004(3) 0.59957(13) 0.43440(9) 0.0289(4) Uani 1 1 d . . . . .
H2A H 0.374291 0.605417 0.456808 0.035 Uiso 1 1 calc R . . . .
H2B H 0.559523 0.544529 0.447656 0.035 Uiso 1 1 calc R . . . .
C8' C 0.8209(3) 0.50165(14) 0.20133(10) 0.0321(4) Uani 1 1 d . . . . .
H8'A H 0.732906 0.480379 0.235553 0.048 Uiso 1 1 calc GR . . . .
H8'B H 0.853345 0.561506 0.210566 0.048 Uiso 1 1 calc GR . . . .
H8'C H 0.938633 0.467114 0.201372 0.048 Uiso 1 1 calc GR . . . .
C15 C 0.1837(4) 0.51126(14) 0.34169(10) 0.0354(5) Uani 1 1 d . . . . .
H15A H 0.057572 0.508524 0.320054 0.053 Uiso 1 1 calc GR . . . .
H15B H 0.168353 0.501824 0.389455 0.053 Uiso 1 1 calc GR . . . .
H15C H 0.267898 0.466973 0.323164 0.053 Uiso 1 1 calc GR . . . .


_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 C7 1.439(2) . ?
O3 C10 1.451(2) . ?
O4 C12 1.200(2) . ?
O2 C12 1.352(2) . ?
O2 C8 1.454(2) . ?
O5 H5 0.8400 . ?
O5 C7' 1.442(2) . ?
O1 C3 1.221(2) . ?
C12 C11 1.536(2) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.322(2) . ?
C5' C4' 1.515(2) . ?
C6' H6' 0.9500 . ?
C6' C7' 1.513(3) . ?
C3' C4' 1.527(2) . ?
C3' C2' 1.325(3) . ?
C3' C10' 1.506(3) . ?
C8 H8 1.0000 . ?
C8 C7 1.538(2) . ?
C8 C9 1.527(3) . ?
C11 C7 1.536(2) . ?
C11 C4' 1.552(2) . ?
C11 C13 1.544(2) . ?
C7 C6 1.538(2) . ?
C4' H4' 1.0000 . ?
C5 C6 1.495(2) . ?
C5 C4 1.344(2) . ?
C5 C1 1.511(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C1' 1.527(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C3 C4 1.470(3) . ?
C3 C2 1.519(3) . ?
C7' C9' 1.518(3) . ?
C7' C8' 1.523(3) . ?
C10 C9 1.535(3) . ?
C10 C1 1.542(3) . ?
C10 C15 1.513(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C4 C14 1.494(3) . ?
C1' H1'A 0.9900 . ?
C1' H1'B 0.9900 . ?
C1' C2' 1.497(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C2' H2' 0.9500 . ?
C1 H1 1.0000 . ?
C1 C2 1.535(2) . ?
C10' H10A 0.9800 . ?
C10' H10B 0.9800 . ?
C10' H10C 0.9800 . ?
C9' H9'A 0.9800 . ?
C9' H9'B 0.9800 . ?
C9' H9'C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C8' H8'A 0.9800 . ?
C8' H8'B 0.9800 . ?
C8' H8'C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C7 O3 C10 105.06(12) . . ?
C12 O2 C8 111.25(13) . . ?
C7' O5 H5 109.5 . . ?
O4 C12 O2 120.82(16) . . ?
O4 C12 C11 128.43(16) . . ?
O2 C12 C11 110.74(14) . . ?
C6' C5' H5' 118.5 . . ?
C6' C5' C4' 122.91(16) . . ?
C4' C5' H5' 118.5 . . ?
C5' C6' H6' 116.7 . . ?
C5' C6' C7' 126.56(16) . . ?
C7' C6' H6' 116.7 . . ?
C2' C3' C4' 123.24(16) . . ?
C2' C3' C10' 121.31(17) . . ?
C10' C3' C4' 115.42(15) . . ?
O2 C8 H8 112.3 . . ?
O2 C8 C7 104.64(13) . . ?
O2 C8 C9 110.29(15) . . ?
C7 C8 H8 112.3 . . ?
C9 C8 H8 112.3 . . ?
C9 C8 C7 104.55(14) . . ?
C12 C11 C7 100.71(13) . . ?
C12 C11 C4' 110.17(13) . . ?
C12 C11 C13 108.43(14) . . ?
C7 C11 C4' 116.26(13) . . ?
C7 C11 C13 110.58(13) . . ?
C13 C11 C4' 110.12(14) . . ?
O3 C7 C8 102.55(13) . . ?
O3 C7 C11 109.50(13) . . ?
O3 C7 C6 109.77(13) . . ?
C11 C7 C8 104.32(13) . . ?
C11 C7 C6 117.72(14) . . ?
C6 C7 C8 111.82(14) . . ?
C5' C4' C3' 108.22(14) . . ?
C5' C4' C11 113.68(14) . . ?
C5' C4' H4' 107.5 . . ?
C3' C4' C11 112.23(14) . . ?
C3' C4' H4' 107.5 . . ?
C11 C4' H4' 107.5 . . ?
C6 C5 C1 117.06(15) . . ?
C4 C5 C6 129.54(17) . . ?
C4 C5 C1 113.31(16) . . ?
C11 C13 H13A 109.2 . . ?
C11 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C1' C13 C11 111.97(15) . . ?
C1' C13 H13A 109.2 . . ?
C1' C13 H13B 109.2 . . ?
C7 C6 H6A 110.0 . . ?
C7 C6 H6B 110.0 . . ?
C5 C6 C7 108.45(14) . . ?
C5 C6 H6A 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
O1 C3 C4 126.17(19) . . ?
O1 C3 C2 125.31(18) . . ?
C4 C3 C2 108.52(16) . . ?
O5 C7' C6' 107.07(15) . . ?
O5 C7' C9' 110.11(15) . . ?
O5 C7' C8' 106.46(15) . . ?
C6' C7' C9' 112.10(15) . . ?
C6' C7' C8' 110.44(15) . . ?
C9' C7' C8' 110.44(17) . . ?
O3 C10 C9 103.23(14) . . ?
O3 C10 C1 105.88(14) . . ?
O3 C10 C15 108.00(15) . . ?
C9 C10 C1 111.96(15) . . ?
C15 C10 C9 114.96(17) . . ?
C15 C10 C1 111.95(16) . . ?
C8 C9 C10 104.31(14) . . ?
C8 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
C10 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
C5 C4 C3 108.70(17) . . ?
C5 C4 C14 129.73(17) . . ?
C3 C4 C14 121.56(16) . . ?
C13 C1' H1'A 109.3 . . ?
C13 C1' H1'B 109.3 . . ?
H1'A C1' H1'B 108.0 . . ?
C2' C1' C13 111.48(15) . . ?
C2' C1' H1'A 109.3 . . ?
C2' C1' H1'B 109.3 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3' C2' C1' 124.43(17) . . ?
C3' C2' H2' 117.8 . . ?
C1' C2' H2' 117.8 . . ?
C5 C1 C10 109.69(14) . . ?
C5 C1 H1 108.4 . . ?
C5 C1 C2 103.79(15) . . ?
C10 C1 H1 108.4 . . ?
C2 C1 C10 117.86(16) . . ?
C2 C1 H1 108.4 . . ?
C3' C10' H10A 109.5 . . ?
C3' C10' H10B 109.5 . . ?
C3' C10' H10C 109.5 . . ?
H10A C10' H10B 109.5 . . ?
H10A C10' H10C 109.5 . . ?
H10B C10' H10C 109.5 . . ?
C7' C9' H9'A 109.5 . . ?
C7' C9' H9'B 109.5 . . ?
C7' C9' H9'C 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
C3 C2 C1 104.38(16) . . ?
C3 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C1 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C7' C8' H8'A 109.5 . . ?
C7' C8' H8'B 109.5 . . ?
C7' C8' H8'C 109.5 . . ?
H8'A C8' H8'B 109.5 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
