# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_hy-20231201_auto
_database_code_depnum_ccdc_archive 'CCDC 2325618'
loop_
_audit_author_name
_audit_author_address
'Yan He'
;Henan Normal University 
China
;
_audit_update_record             
;
2024-01-15 deposited with the CCDC.	2025-01-08 downloaded from the CCDC.
;
_audit_creation_date             2023-12-05
_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         'C21 H29 O4'
_chemical_formula_sum            'C21 H29 O4'
_chemical_formula_weight         345.44
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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                   6.09540(10)
_cell_length_b                   12.03060(10)
_cell_length_c                   26.9927(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1979.41(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12881
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2160
_cell_measurement_theta_min      4.9040
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.858
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            26116
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.463
_diffrn_reflns_theta_min         4.023
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00 106.00   1.00    1.56    --   35.62  13.00 -39.00  113
  2  ω     54.00 109.00   1.00    1.56    --   35.62-174.00-132.00   55
  3  ω     40.00 109.00   1.00    6.24    --  106.81-114.00   6.00   69
  4  ω     92.00 175.00   1.00    6.24    --  106.81 136.00  -5.00   83
  5  ω     64.00 177.00   1.00    6.24    --  106.81  13.00 -39.00  113
  6  ω   -105.00 -17.00   1.00    1.56    --  -35.62 -38.00 -90.00   88
  7  ω      6.00  74.00   1.00    1.56    --   35.62 -99.00-180.00   68
  8  ω     61.00 108.00   1.00    1.56    --   35.62 178.00-180.00   47
  9  ω    103.00 174.00   1.00    6.24    --  106.81  77.00  30.00   71
 10  ω     37.00 107.00   1.00    6.24    --  106.81 -95.00  30.00   70
 11  ω     38.00 124.00   1.00    6.24    --  106.81 -45.00  30.00   86
 12  ω     37.00 128.00   1.00    6.24    --  106.81 -30.00 -60.00   91
 13  ω     40.00 125.00   1.00    6.24    --  106.81 -61.00-120.00   85
 14  ω   -105.00 -17.00   1.00    1.56    --  -35.62 -38.00   0.00   88
 15  ω   -103.00 -19.00   1.00    1.56    --  -35.62 -57.00-180.00   84
 16  ω   -105.00 -17.00   1.00    1.56    --  -35.62 -38.00  90.00   88
 17  ω     58.00 108.00   1.00    1.56    --   35.62-178.00  30.00   50
 18  ω     85.00 177.00   1.00    6.24    --  106.81  30.00  90.00   92
 19  ω     85.00 177.00   1.00    6.24    --  106.81  30.00-150.00   92
 20  ω     89.00 175.00   1.00    6.24    --  106.81  45.00   0.00   86
 21  ω     89.00 175.00   1.00    6.24    --  106.81  45.00 150.00   86
 22  ω     85.00 177.00   1.00    6.24    --  106.81  30.00 120.00   92
 23  ω     89.00 175.00   1.00    6.24    --  106.81  45.00-120.00   86
 24  ω     85.00 177.00   1.00    6.24    --  106.81  30.00  60.00   92
 25  ω     61.00 146.00   1.00    6.24    --  106.81 178.00 -90.00   85
 26  ω   -103.00 -19.00   1.00    1.56    --  -35.62 -57.00-120.00   84
 27  ω   -103.00 -19.00   1.00    1.56    --  -35.62 -57.00 -30.00   84
 28  ω   -108.00 -39.00   1.00    1.56    --  -35.62-178.00-120.00   69
 29  ω   -108.00 -37.00   1.00    1.56    --  -35.62 178.00 150.00   71
 30  ω     89.00 174.00   1.00    6.24    --  106.81  61.00 150.00   85
 31  ω     89.00 175.00   1.00    6.24    --  106.81  45.00 120.00   86
 32  ω     89.00 175.00   1.00    6.24    --  106.81  45.00 -30.00   86
 33  ω     89.00 144.00   1.00    6.24    --  106.81  45.00-150.00   55
 34  ω     37.00 107.00   1.00    6.24    --  106.81 -95.00  90.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0253923000
_diffrn_orient_matrix_UB_12      -0.0774213000
_diffrn_orient_matrix_UB_13      0.0451084000
_diffrn_orient_matrix_UB_21      0.0384829000
_diffrn_orient_matrix_UB_22      -0.0993157000
_diffrn_orient_matrix_UB_23      -0.0349649000
_diffrn_orient_matrix_UB_31      0.2484622000
_diffrn_orient_matrix_UB_32      0.0232813000
_diffrn_orient_matrix_UB_33      0.0008221000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3660
_reflns_number_total             3832
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 1417 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3832
_refine_ls_number_restraints     972
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0807
_refine_ls_restrained_S_all      1.219
_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)+(0.1469P)²+1.1771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2370
_refine_ls_wR_factor_ref         0.2405
_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. Uiso/Uaniso restraints and constraints
C004 \\sim C005 \\sim C006 \\sim C008 \\sim C009 \\sim C00A \\sim C00B \\sim
C00C \\sim C00D \\sim C00E \\sim C00F \\sim C00G \\sim C00H \\sim C00I \\sim
C00J \\sim C00K \\sim C00L \\sim C00M \\sim C00N \\sim C00O \\sim C00P: within
6.3A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 6.3A
3.a Ternary CH refined with riding coordinates:
 C005(H005), C00A(H00A), C00D(H00D)
3.b Secondary CH2 refined with riding coordinates:
 C00E(H00B,H00C), C00F(H00E,H00F), C00L(H00O,H00P)
3.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00G(H00G), C00I(H00K)
3.d Idealised Me refined as rotating group:
 C00H(H00H,H00I,H00J), C00J(H00L,H00M,H00N), C00M(H00Q,H00R,H00S), C00O(H00T,
 H00U,H00V), C00P(H00W,H00X,H00Y)
3.e Idealised tetrahedral OH refined as rotating group:
 O002(H002), O003(H003)
;
_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
O001 O 0.2466(6) -0.0699(3) 0.43916(14) 0.0642(10) Uani 1 1 d . . . . .
O002 O -0.0066(8) 0.1186(3) 0.47285(13) 0.0690(11) Uani 1 1 d . . . . .
H002 H 0.115813 0.100389 0.482512 0.103 Uiso 1 1 calc R U . . .
O003 O 0.3658(9) 0.2215(3) 0.45854(14) 0.0766(13) Uani 1 1 d . . . . .
H003 H 0.448507 0.270005 0.468837 0.115 Uiso 1 1 calc R U . . .
C004 C 0.2114(7) 0.2783(3) 0.34090(15) 0.0406(8) Uani 1 1 d . U . . .
C005 C 0.0798(6) 0.1067(3) 0.38396(14) 0.0355(7) Uani 1 1 d . U . . .
H005 H 0.235993 0.091258 0.389058 0.043 Uiso 1 1 calc R U . . .
C006 C 0.0690(7) 0.1750(3) 0.33519(15) 0.0395(8) Uani 1 1 d . U . . .
O007 O -0.0844(9) -0.1451(4) 0.4475(2) 0.1062(19) Uani 1 1 d . . . . .
C008 C 0.2505(8) 0.3254(3) 0.38748(17) 0.0476(9) Uani 1 1 d . U . . .
C009 C 0.2981(8) 0.3341(4) 0.30031(18) 0.0534(10) Uani 1 1 d . U . . .
H009 H 0.277465 0.305181 0.268687 0.064 Uiso 1 1 calc R U . . .
C00A C 0.0130(8) 0.1799(3) 0.42758(16) 0.0472(9) Uani 1 1 d . U . . .
H00A H -0.129246 0.213998 0.420082 0.057 Uiso 1 1 calc R U . . .
C00B C -0.0328(7) -0.0097(3) 0.38260(18) 0.0462(9) Uani 1 1 d . U . . .
C00C C 0.0352(8) -0.0812(4) 0.4271(2) 0.0562(11) Uani 1 1 d . U . . .
C00D C 0.1811(9) 0.2719(4) 0.43478(18) 0.0535(10) Uani 1 1 d . U . . .
H00D H 0.119397 0.328708 0.456761 0.064 Uiso 1 1 calc R U . . .
C00E C 0.1567(9) 0.1012(4) 0.29279(17) 0.0524(10) Uani 1 1 d . U . . .
H00B H 0.139595 0.140220 0.261586 0.063 Uiso 1 1 calc R U . . .
H00C H 0.312024 0.087901 0.297852 0.063 Uiso 1 1 calc R U . . .
C00F C 0.0577(9) -0.0736(4) 0.3377(2) 0.0574(10) Uani 1 1 d . U . . .
H00E H 0.210967 -0.090800 0.343575 0.069 Uiso 1 1 calc R U . . .
H00F H -0.020913 -0.143299 0.334573 0.069 Uiso 1 1 calc R U . . .
C00G C 0.3674(9) 0.4255(4) 0.3919(2) 0.0610(11) Uani 1 1 d . U . . .
H00G H 0.389101 0.455065 0.423354 0.073 Uiso 1 1 calc R U . . .
C00H C -0.1623(8) 0.2199(4) 0.3214(2) 0.0583(12) Uani 1 1 d . U . . .
H00H H -0.221650 0.260509 0.348946 0.087 Uiso 1 1 calc R U . . .
H00I H -0.257379 0.158719 0.313594 0.087 Uiso 1 1 calc R U . . .
H00J H -0.150820 0.268150 0.293218 0.087 Uiso 1 1 calc R U . . .
C00I C 0.4158(9) 0.4329(4) 0.3062(2) 0.0629(11) Uani 1 1 d . U . . .
H00K H 0.473226 0.467988 0.278409 0.075 Uiso 1 1 calc R U . . .
C00J C -0.2863(8) -0.0044(5) 0.3823(3) 0.0693(14) Uani 1 1 d . U . . .
H00L H -0.335384 0.044421 0.408168 0.104 Uiso 1 1 calc R U . . .
H00M H -0.344899 -0.077481 0.387760 0.104 Uiso 1 1 calc R U . . .
H00N H -0.335893 0.023070 0.350876 0.104 Uiso 1 1 calc R U . . .
C00K C 0.4492(9) 0.4801(4) 0.3528(2) 0.0648(12) Uani 1 1 d . U . . .
C00L C 0.0379(10) -0.0098(4) 0.2898(2) 0.0632(11) Uani 1 1 d . U . . .
H00O H -0.115824 0.002994 0.282473 0.076 Uiso 1 1 calc R U . . .
H00P H 0.099631 -0.053551 0.263014 0.076 Uiso 1 1 calc R U . . .
C00M C 0.3305(13) -0.1424(6) 0.4772(3) 0.0885(19) Uani 1 1 d . U . . .
H00Q H 0.322123 -0.218056 0.466050 0.133 Uiso 1 1 calc R U . . .
H00R H 0.244698 -0.133731 0.506730 0.133 Uiso 1 1 calc R U . . .
H00S H 0.480552 -0.123646 0.484010 0.133 Uiso 1 1 calc R U . . .
C00N C 0.5751(12) 0.5896(5) 0.3596(3) 0.0842(15) Uani 1 1 d . U . . .
C00O C 0.8068(14) 0.5725(7) 0.3663(4) 0.106(2) Uani 1 1 d . U . . .
H00T H 0.830246 0.514067 0.389889 0.159 Uiso 1 1 calc R U . . .
H00U H 0.872915 0.639849 0.378170 0.159 Uiso 1 1 calc R U . . .
H00V H 0.871911 0.552270 0.335166 0.159 Uiso 1 1 calc R U . . .
C00P C 0.4738(18) 0.6817(6) 0.3361(4) 0.116(3) Uani 1 1 d . U . . .
H00W H 0.405276 0.657558 0.305921 0.173 Uiso 1 1 calc R U . . .
H00X H 0.582675 0.736913 0.328665 0.173 Uiso 1 1 calc R U . . .
H00Y H 0.365059 0.712901 0.357710 0.173 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
O001 C00C 1.336(7) . ?
O001 C00M 1.440(7) . ?
O002 H002 0.8200 . ?
O002 C00A 1.432(5) . ?
O003 H003 0.8200 . ?
O003 C00D 1.431(7) . ?
C004 C006 1.524(5) . ?
C004 C008 1.400(6) . ?
C004 C009 1.389(6) . ?
C005 H005 0.9800 . ?
C005 C006 1.553(5) . ?
C005 C00A 1.526(5) . ?
C005 C00B 1.560(5) . ?
C006 C00E 1.544(6) . ?
C006 C00H 1.555(6) . ?
O007 C00C 1.194(6) . ?
C008 C00D 1.491(7) . ?
C008 C00G 1.404(6) . ?
C009 H009 0.9300 . ?
C009 C00I 1.398(7) . ?
C00A H00A 0.9800 . ?
C00A C00D 1.521(7) . ?
C00B C00C 1.534(7) . ?
C00B C00F 1.536(6) . ?
C00B C00J 1.547(6) . ?
C00D H00D 0.9800 . ?
C00E H00B 0.9700 . ?
C00E H00C 0.9700 . ?
C00E C00L 1.520(7) . ?
C00F H00E 0.9700 . ?
C00F H00F 0.9700 . ?
C00F C00L 1.510(8) . ?
C00G H00G 0.9300 . ?
C00G C00K 1.340(8) . ?
C00H H00H 0.9600 . ?
C00H H00I 0.9600 . ?
C00H H00J 0.9600 . ?
C00I H00K 0.9300 . ?
C00I C00K 1.395(9) . ?
C00J H00L 0.9600 . ?
C00J H00M 0.9600 . ?
C00J H00N 0.9600 . ?
C00K C00N 1.535(8) . ?
C00L H00O 0.9700 . ?
C00L H00P 0.9700 . ?
C00M H00Q 0.9600 . ?
C00M H00R 0.9600 . ?
C00M H00S 0.9600 . ?
C00N C00O 1.438(11) . ?
C00N C00P 1.419(11) . ?
C00O H00T 0.9600 . ?
C00O H00U 0.9600 . ?
C00O H00V 0.9600 . ?
C00P H00W 0.9600 . ?
C00P H00X 0.9600 . ?
C00P H00Y 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
C00C O001 C00M 117.0(4) . . ?
C00A O002 H002 109.5 . . ?
C00D O003 H003 109.5 . . ?
C008 C004 C006 121.2(4) . . ?
C009 C004 C006 122.1(4) . . ?
C009 C004 C008 116.6(4) . . ?
C006 C005 H005 105.1 . . ?
C006 C005 C00B 115.9(3) . . ?
C00A C005 H005 105.1 . . ?
C00A C005 C006 109.7(3) . . ?
C00A C005 C00B 114.8(3) . . ?
C00B C005 H005 105.1 . . ?
C004 C006 C005 108.8(3) . . ?
C004 C006 C00E 110.3(3) . . ?
C004 C006 C00H 104.9(3) . . ?
C005 C006 C00H 115.1(4) . . ?
C00E C006 C005 108.0(3) . . ?
C00E C006 C00H 109.7(4) . . ?
C004 C008 C00D 123.1(4) . . ?
C004 C008 C00G 120.7(4) . . ?
C00G C008 C00D 116.2(4) . . ?
C004 C009 H009 119.5 . . ?
C004 C009 C00I 121.1(5) . . ?
C00I C009 H009 119.5 . . ?
O002 C00A C005 112.5(3) . . ?
O002 C00A H00A 108.5 . . ?
O002 C00A C00D 108.8(4) . . ?
C005 C00A H00A 108.5 . . ?
C00D C00A C005 109.8(3) . . ?
C00D C00A H00A 108.5 . . ?
C00C C00B C005 111.5(4) . . ?
C00C C00B C00F 103.9(4) . . ?
C00C C00B C00J 107.3(4) . . ?
C00F C00B C005 108.0(3) . . ?
C00F C00B C00J 112.0(4) . . ?
C00J C00B C005 113.7(4) . . ?
O001 C00C C00B 113.2(4) . . ?
O007 C00C O001 122.9(5) . . ?
O007 C00C C00B 123.9(5) . . ?
O003 C00D C008 110.1(5) . . ?
O003 C00D C00A 106.2(4) . . ?
O003 C00D H00D 109.0 . . ?
C008 C00D C00A 113.3(4) . . ?
C008 C00D H00D 109.0 . . ?
C00A C00D H00D 109.0 . . ?
C006 C00E H00B 109.1 . . ?
C006 C00E H00C 109.1 . . ?
H00B C00E H00C 107.9 . . ?
C00L C00E C006 112.3(4) . . ?
C00L C00E H00B 109.1 . . ?
C00L C00E H00C 109.1 . . ?
C00B C00F H00E 108.9 . . ?
C00B C00F H00F 108.9 . . ?
H00E C00F H00F 107.8 . . ?
C00L C00F C00B 113.2(4) . . ?
C00L C00F H00E 108.9 . . ?
C00L C00F H00F 108.9 . . ?
C008 C00G H00G 118.6 . . ?
C00K C00G C008 122.9(5) . . ?
C00K C00G H00G 118.6 . . ?
C006 C00H H00H 109.5 . . ?
C006 C00H H00I 109.5 . . ?
C006 C00H H00J 109.5 . . ?
H00H C00H H00I 109.5 . . ?
H00H C00H H00J 109.5 . . ?
H00I C00H H00J 109.5 . . ?
C009 C00I H00K 119.2 . . ?
C00K C00I C009 121.7(5) . . ?
C00K C00I H00K 119.2 . . ?
C00B C00J H00L 109.5 . . ?
C00B C00J H00M 109.5 . . ?
C00B C00J H00N 109.5 . . ?
H00L C00J H00M 109.5 . . ?
H00L C00J H00N 109.5 . . ?
H00M C00J H00N 109.5 . . ?
C00G C00K C00I 117.1(5) . . ?
C00G C00K C00N 120.8(6) . . ?
C00I C00K C00N 122.1(5) . . ?
C00E C00L H00O 109.4 . . ?
C00E C00L H00P 109.4 . . ?
C00F C00L C00E 111.3(4) . . ?
C00F C00L H00O 109.4 . . ?
C00F C00L H00P 109.4 . . ?
H00O C00L H00P 108.0 . . ?
O001 C00M H00Q 109.5 . . ?
O001 C00M H00R 109.5 . . ?
O001 C00M H00S 109.5 . . ?
H00Q C00M H00R 109.5 . . ?
H00Q C00M H00S 109.5 . . ?
H00R C00M H00S 109.5 . . ?
C00O C00N C00K 112.5(6) . . ?
C00P C00N C00K 113.5(6) . . ?
C00P C00N C00O 126.5(7) . . ?
C00N C00O H00T 109.5 . . ?
C00N C00O H00U 109.5 . . ?
C00N C00O H00V 109.5 . . ?
H00T C00O H00U 109.5 . . ?
H00T C00O H00V 109.5 . . ?
H00U C00O H00V 109.5 . . ?
C00N C00P H00W 109.5 . . ?
C00N C00P H00X 109.5 . . ?
C00N C00P H00Y 109.5 . . ?
H00W C00P H00X 109.5 . . ?
H00W C00P H00Y 109.5 . . ?
H00X C00P H00Y 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
O002 C00A C00D O003 46.6(5) . . . . ?
O002 C00A C00D C008 167.5(4) . . . . ?
C004 C006 C00E C00L 172.8(4) . . . . ?
C004 C008 C00D O003 103.0(5) . . . . ?
C004 C008 C00D C00A -15.8(6) . . . . ?
C004 C008 C00G C00K -0.7(8) . . . . ?
C004 C009 C00I C00K -0.7(8) . . . . ?
C005 C006 C00E C00L 54.0(5) . . . . ?
C005 C00A C00D O003 -77.0(5) . . . . ?
C005 C00A C00D C008 44.0(5) . . . . ?
C005 C00B C00C O001 -38.9(5) . . . . ?
C005 C00B C00C O007 144.8(6) . . . . ?
C005 C00B C00F C00L -53.3(5) . . . . ?
C006 C004 C008 C00D 7.7(6) . . . . ?
C006 C004 C008 C00G -174.9(4) . . . . ?
C006 C004 C009 C00I 175.6(4) . . . . ?
C006 C005 C00A O002 172.8(4) . . . . ?
C006 C005 C00A C00D -65.8(4) . . . . ?
C006 C005 C00B C00C 165.8(4) . . . . ?
C006 C005 C00B C00F 52.2(5) . . . . ?
C006 C005 C00B C00J -72.8(5) . . . . ?
C006 C00E C00L C00F -58.3(6) . . . . ?
C008 C004 C006 C005 -27.1(5) . . . . ?
C008 C004 C006 C00E -145.4(4) . . . . ?
C008 C004 C006 C00H 96.6(4) . . . . ?
C008 C004 C009 C00I -0.7(7) . . . . ?
C008 C00G C00K C00I -0.7(8) . . . . ?
C008 C00G C00K C00N 179.7(5) . . . . ?
C009 C004 C006 C005 156.7(4) . . . . ?
C009 C004 C006 C00E 38.4(5) . . . . ?
C009 C004 C006 C00H -79.6(5) . . . . ?
C009 C004 C008 C00D -175.9(4) . . . . ?
C009 C004 C008 C00G 1.4(6) . . . . ?
C009 C00I C00K C00G 1.4(8) . . . . ?
C009 C00I C00K C00N -179.0(5) . . . . ?
C00A C005 C006 C004 55.4(4) . . . . ?
C00A C005 C006 C00E 175.2(3) . . . . ?
C00A C005 C006 C00H -61.9(5) . . . . ?
C00A C005 C00B C00C -64.6(5) . . . . ?
C00A C005 C00B C00F -178.2(4) . . . . ?
C00A C005 C00B C00J 56.8(6) . . . . ?
C00B C005 C006 C004 -172.6(3) . . . . ?
C00B C005 C006 C00E -52.8(4) . . . . ?
C00B C005 C006 C00H 70.1(4) . . . . ?
C00B C005 C00A O002 40.3(5) . . . . ?
C00B C005 C00A C00D 161.6(4) . . . . ?
C00B C00F C00L C00E 58.1(6) . . . . ?
C00C C00B C00F C00L -171.8(4) . . . . ?
C00D C008 C00G C00K 176.8(5) . . . . ?
C00F C00B C00C O001 77.2(5) . . . . ?
C00F C00B C00C O007 -99.1(6) . . . . ?
C00G C008 C00D O003 -74.5(5) . . . . ?
C00G C008 C00D C00A 166.8(4) . . . . ?
C00G C00K C00N C00O 90.1(9) . . . . ?
C00G C00K C00N C00P -118.1(9) . . . . ?
C00H C006 C00E C00L -72.2(5) . . . . ?
C00I C00K C00N C00O -89.5(8) . . . . ?
C00I C00K C00N C00P 62.3(10) . . . . ?
C00J C00B C00C O001 -164.0(5) . . . . ?
C00J C00B C00C O007 19.7(8) . . . . ?
C00J C00B C00F C00L 72.8(6) . . . . ?
C00M O001 C00C O007 2.7(9) . . . . ?
C00M O001 C00C C00B -173.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.430
_oxdiff_exptl_absorpt_empirical_full_min 0.445
####################################################################### 
# 
# 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_20240102
_database_code_depnum_ccdc_archive 'CCDC 2325639'
loop_
_audit_author_name
_audit_author_address
'Yan He'
;Henan Normal University 
China
;
_audit_update_record             
;
2024-01-15 deposited with the CCDC.	2025-01-08 downloaded from the CCDC.
;
_audit_creation_date             2024-01-02
_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         'C21 H30 O4, C H4 O'
_chemical_formula_sum            'C22 H34 O5'
_chemical_formula_weight         378.49
_chemical_absolute_configuration ad
_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                   13.6015(7)
_cell_length_b                   6.0925(2)
_cell_length_c                   13.7972(7)
_cell_angle_alpha                90
_cell_angle_beta                 116.481(7)
_cell_angle_gamma                90
_cell_volume                     1023.38(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6693
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.5490
_cell_measurement_theta_min      3.5610
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9110
_diffrn_reflns_point_group_measured_fraction_full 0.898
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.070
_diffrn_reflns_theta_min         3.579
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00 -28.00   0.50    0.17    --  -42.21  57.00 -90.00   76
  2  ω    -22.00  26.00   0.50    0.17    --  -42.21  57.00 -90.00   96
  3  ω    -26.00  34.00   0.50    0.17    --  -42.21  19.00 -60.00  120
  4  ω     72.00 116.00   0.50    1.20    --  113.62-125.00 150.00   88
  5  ω     44.00  70.00   0.50    1.20    --  113.62-125.00 150.00   52
  6  ω     41.00 103.00   0.50    1.20    --  113.62 -95.00 150.00  124
  7  ω     54.00 113.00   0.50    1.20    --  113.62-125.00  90.00  118
  8  ω     83.00 116.00   0.50    1.20    --  113.62-125.00 -30.00   66
  9  ω     52.00 115.00   0.50    1.20    --  113.62-125.00 -90.00  126
 10  ω     37.00  89.00   0.50    1.20    --  113.62 -95.00 -30.00  104
 11  ω    -36.00  41.00   0.50    0.17    --   42.21 -38.00  90.00  154
 12  ω     53.00 103.00   0.50    1.20    --  113.62 -77.00 150.00  100
 13  ω     43.00  70.00   0.50    1.20    --  113.62 -61.00   0.00   54
 14  ω     41.00  68.00   0.50    1.20    --  113.62 -61.00 -30.00   54
 15  ω     61.00 177.00   0.50    1.20    --  113.62  15.00-120.00  232
 16  ω    135.00 164.00   0.50    1.20    --  113.62  45.00 -60.00   58
 17  ω     89.00 121.00   0.50    1.20    --  113.62  45.00 -60.00   64
 18  ω     89.00 149.00   0.50    1.20    --  113.62  45.00  90.00  120
 19  ω     92.00 164.00   0.50    1.20    --  113.62 125.00  60.00  144
 20  ω     74.00 113.00   0.50    0.17    --   42.21 178.00  90.00   78
 21  ω     60.00  91.00   0.50    0.17    --   42.21 178.00  60.00   62
 22  ω   -104.00 -47.00   0.50    1.20    --  -96.00  77.00  90.00  114
 23  ω    -71.00 -23.00   0.50    1.20    --  -96.00  61.00 -60.00   96
 24  ω    -71.00 -29.00   0.50    1.20    --  -96.00  61.00 -90.00   84
 25  ω   -176.00 -51.00   0.50    1.20    --  -96.00 -15.00   0.00  250
 26  ω   -143.00 -70.00   0.50    1.20    --  -96.00 -45.00 -30.00  146
 27  ω   -162.00-109.00   0.50    1.20    --  -96.00 -95.00  60.00  106
 28  ω   -122.00  -2.00   0.50    0.17    --  -42.21 -19.00 120.00  240
 29  ω    -85.00 -39.00   0.50    1.20    --  -96.00 125.00  60.00   92
 30  ω    -80.00 -25.00   0.50    1.20    --  -96.00 125.00  90.00  110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1024179000
_diffrn_orient_matrix_UB_12      -0.1271820000
_diffrn_orient_matrix_UB_13      0.0107477000
_diffrn_orient_matrix_UB_21      0.0649228000
_diffrn_orient_matrix_UB_22      0.0875840000
_diffrn_orient_matrix_UB_23      0.1162150000
_diffrn_orient_matrix_UB_31      -0.0363437000
_diffrn_orient_matrix_UB_32      -0.2002739000
_diffrn_orient_matrix_UB_33      0.0439604000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.577
_reflns_Friedel_fraction_full    0.773
_reflns_Friedel_fraction_max     0.679
_reflns_number_gt                3476
_reflns_number_total             3636
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1234 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3636
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.074
_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)+(0.0649P)²+0.1127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1037
_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:
 C006(H006), C008(H008), C00B(H00B), C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00D), C00J(H00E,H00F), C00P(H00U,H00V)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00C), C00I(H00I)
2.d Idealised Me refined as rotating group:
 C00K(H00H,H00J,H00K), C00L(H00L,H00M,H00N), C00N(H00O,H00P,H00Q), C00O(H00R,
 H00S,H00T), C00Q(H00Z,H,HA), C00R(H00W,H00X,H00Y)
2.e Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002)
;
_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
O001 O 0.48283(11) 0.5781(3) 0.42865(12) 0.0216(3) Uani 1 1 d . . . . .
H001 H 0.491755 0.696333 0.402221 0.032 Uiso 1 1 calc R U . . .
O002 O 0.36527(12) 0.7638(3) 0.53788(11) 0.0212(3) Uani 1 1 d . . . . .
H002 H 0.416274 0.856293 0.556900 0.032 Uiso 1 1 calc R U . . .
O003 O 0.19571(14) 0.5348(3) 0.57388(13) 0.0270(4) Uani 1 1 d . . . . .
O004 O 0.19849(14) 0.8822(3) 0.62688(13) 0.0281(4) Uani 1 1 d . . . . .
O005 O 0.53907(14) 0.8966(3) 0.32790(13) 0.0289(4) Uani 1 1 d . . . . .
C006 C 0.36817(16) 0.5422(4) 0.39400(16) 0.0194(4) Uani 1 1 d . . . . .
H006 H 0.361159 0.412633 0.434962 0.023 Uiso 1 1 calc R U . . .
C007 C 0.18195(17) 0.7270(4) 0.55173(18) 0.0227(4) Uani 1 1 d . . . . .
C008 C 0.31628(16) 0.7374(4) 0.42284(15) 0.0185(4) Uani 1 1 d . . . . .
H008 H 0.328106 0.873421 0.388858 0.022 Uiso 1 1 calc R U . . .
C009 C 0.36175(17) 0.3563(4) 0.22905(17) 0.0211(4) Uani 1 1 d . . . . .
H009 H 0.433927 0.305768 0.274468 0.025 Uiso 1 1 calc R U . . .
C00A C 0.19984(17) 0.5557(3) 0.20938(17) 0.0201(4) Uani 1 1 d . . . . .
C00B C 0.19258(16) 0.6920(3) 0.37754(17) 0.0195(4) Uani 1 1 d . . . . .
H00B H 0.187003 0.533568 0.393428 0.023 Uiso 1 1 calc R U . . .
C00C C 0.20702(18) 0.3722(4) 0.05556(17) 0.0237(4) Uani 1 1 d . . . . .
H00C H 0.172128 0.336022 -0.019263 0.028 Uiso 1 1 calc R U . . .
C00D C 0.31337(18) 0.2988(4) 0.12041(17) 0.0223(4) Uani 1 1 d . . . . .
C00E C 0.30747(16) 0.4867(3) 0.27409(16) 0.0192(4) Uani 1 1 d . . . . .
C00F C 0.01271(17) 0.7487(4) 0.38455(18) 0.0254(4) Uani 1 1 d . . . . .
H00A H 0.007742 0.594888 0.405076 0.030 Uiso 1 1 calc R U . . .
H00D H -0.026862 0.841968 0.414405 0.030 Uiso 1 1 calc R U . . .
C00G C 0.37435(18) 0.1563(4) 0.07452(17) 0.0243(5) Uani 1 1 d . . . . .
H00G H 0.450603 0.133901 0.133092 0.029 Uiso 1 1 calc R U . . .
C00H C 0.13741(16) 0.7085(3) 0.25137(17) 0.0201(4) Uani 1 1 d . . . . .
C00I C 0.15142(17) 0.4982(4) 0.09952(18) 0.0237(4) Uani 1 1 d . . . . .
H00I H 0.078854 0.546365 0.053902 0.028 Uiso 1 1 calc R U . . .
C00J C 0.01696(16) 0.6318(4) 0.21067(17) 0.0243(4) Uani 1 1 d . . . . .
H00E H -0.021825 0.645768 0.130857 0.029 Uiso 1 1 calc R U . . .
H00F H 0.016060 0.475110 0.229208 0.029 Uiso 1 1 calc R U . . .
C00K C 0.1474(2) 1.0678(4) 0.43621(19) 0.0262(5) Uani 1 1 d . . . . .
H00H H 0.119562 1.133331 0.484006 0.039 Uiso 1 1 calc R U . . .
H00J H 0.105228 1.123914 0.362482 0.039 Uiso 1 1 calc R U . . .
H00K H 0.225036 1.105977 0.462209 0.039 Uiso 1 1 calc R U . . .
C00L C 0.13832(18) 0.9384(4) 0.20398(17) 0.0244(4) Uani 1 1 d . . . . .
H00L H 0.213314 0.996908 0.237316 0.037 Uiso 1 1 calc R U . . .
H00M H 0.089999 1.037252 0.219117 0.037 Uiso 1 1 calc R U . . .
H00N H 0.112237 0.926700 0.125521 0.037 Uiso 1 1 calc R U . . .
C00M C 0.13546(17) 0.8186(4) 0.43609(18) 0.0214(4) Uani 1 1 d . . . . .
C00N C 0.3211(2) -0.0688(4) 0.0411(2) 0.0317(5) Uani 1 1 d . . . . .
H00O H 0.320691 -0.142379 0.104131 0.048 Uiso 1 1 calc R U . . .
H00P H 0.362822 -0.157270 0.012977 0.048 Uiso 1 1 calc R U . . .
H00Q H 0.245426 -0.051673 -0.015202 0.048 Uiso 1 1 calc R U . . .
C00O C 0.3833(2) 0.2699(4) -0.0203(2) 0.0314(5) Uani 1 1 d . . . . .
H00R H 0.309669 0.288688 -0.080210 0.047 Uiso 1 1 calc R U . . .
H00S H 0.427887 0.179794 -0.044371 0.047 Uiso 1 1 calc R U . . .
H00T H 0.417898 0.413938 0.003066 0.047 Uiso 1 1 calc R U . . .
C00P C -0.04371(17) 0.7674(4) 0.26112(19) 0.0276(5) Uani 1 1 d . . . . .
H00U H -0.045628 0.923276 0.240099 0.033 Uiso 1 1 calc R U . . .
H00V H -0.120417 0.714845 0.232843 0.033 Uiso 1 1 calc R U . . .
C00Q C 0.5913(2) 0.7730(4) 0.2762(2) 0.0312(5) Uani 1 1 d . . . . .
H00Z H 0.606130 0.868643 0.227148 0.047 Uiso 1 1 calc R U . . .
H H 0.543005 0.652628 0.234788 0.047 Uiso 1 1 calc R U . . .
HA H 0.660565 0.712643 0.331084 0.047 Uiso 1 1 calc R U . . .
C00R C 0.2423(3) 0.8018(5) 0.7362(2) 0.0386(6) Uani 1 1 d . . . . .
H00W H 0.191715 0.693500 0.741674 0.058 Uiso 1 1 calc R U . . .
H00X H 0.251120 0.924380 0.785452 0.058 Uiso 1 1 calc R U . . .
H00Y H 0.313793 0.732930 0.756008 0.058 Uiso 1 1 calc R U . . .
H005 H 0.579(3) 1.002(7) 0.368(3) 0.044(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 H001 0.8400 . ?
O001 C006 1.430(2) . ?
O002 H002 0.8400 . ?
O002 C008 1.430(2) . ?
O003 C007 1.203(3) . ?
O004 C007 1.346(3) . ?
O004 C00R 1.438(3) . ?
O005 C00Q 1.426(3) . ?
O005 H005 0.86(4) . ?
C006 H006 1.0000 . ?
C006 C008 1.523(3) . ?
C006 C00E 1.522(3) . ?
C007 C00M 1.535(3) . ?
C008 H008 1.0000 . ?
C008 C00B 1.536(3) . ?
C009 H009 0.9500 . ?
C009 C00D 1.387(3) . ?
C009 C00E 1.404(3) . ?
C00A C00E 1.397(3) . ?
C00A C00H 1.537(3) . ?
C00A C00I 1.401(3) . ?
C00B H00B 1.0000 . ?
C00B C00H 1.562(3) . ?
C00B C00M 1.553(3) . ?
C00C H00C 0.9500 . ?
C00C C00D 1.393(3) . ?
C00C C00I 1.392(3) . ?
C00D C00G 1.520(3) . ?
C00F H00A 0.9900 . ?
C00F H00D 0.9900 . ?
C00F C00M 1.554(3) . ?
C00F C00P 1.529(3) . ?
C00G H00G 1.0000 . ?
C00G C00N 1.524(3) . ?
C00G C00O 1.532(3) . ?
C00H C00J 1.548(3) . ?
C00H C00L 1.548(3) . ?
C00I H00I 0.9500 . ?
C00J H00E 0.9900 . ?
C00J H00F 0.9900 . ?
C00J C00P 1.536(3) . ?
C00K H00H 0.9800 . ?
C00K H00J 0.9800 . ?
C00K H00K 0.9800 . ?
C00K C00M 1.527(3) . ?
C00L H00L 0.9800 . ?
C00L H00M 0.9800 . ?
C00L H00N 0.9800 . ?
C00N H00O 0.9800 . ?
C00N H00P 0.9800 . ?
C00N H00Q 0.9800 . ?
C00O H00R 0.9800 . ?
C00O H00S 0.9800 . ?
C00O H00T 0.9800 . ?
C00P H00U 0.9900 . ?
C00P H00V 0.9900 . ?
C00Q H00Z 0.9800 . ?
C00Q H 0.9800 . ?
C00Q HA 0.9800 . ?
C00R H00W 0.9800 . ?
C00R H00X 0.9800 . ?
C00R H00Y 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
C006 O001 H001 109.5 . . ?
C008 O002 H002 109.5 . . ?
C007 O004 C00R 114.7(2) . . ?
C00Q O005 H005 114(2) . . ?
O001 C006 H006 107.3 . . ?
O001 C006 C008 110.89(17) . . ?
O001 C006 C00E 112.31(15) . . ?
C008 C006 H006 107.3 . . ?
C00E C006 H006 107.3 . . ?
C00E C006 C008 111.57(16) . . ?
O003 C007 O004 122.3(2) . . ?
O003 C007 C00M 124.3(2) . . ?
O004 C007 C00M 113.3(2) . . ?
O002 C008 C006 109.68(16) . . ?
O002 C008 H008 109.5 . . ?
O002 C008 C00B 110.82(15) . . ?
C006 C008 H008 109.5 . . ?
C006 C008 C00B 107.71(16) . . ?
C00B C008 H008 109.5 . . ?
C00D C009 H009 118.9 . . ?
C00D C009 C00E 122.12(19) . . ?
C00E C009 H009 118.9 . . ?
C00E C00A C00H 122.63(19) . . ?
C00E C00A C00I 117.96(19) . . ?
C00I C00A C00H 119.16(18) . . ?
C008 C00B H00B 105.1 . . ?
C008 C00B C00H 109.67(16) . . ?
C008 C00B C00M 114.22(17) . . ?
C00H C00B H00B 105.1 . . ?
C00M C00B H00B 105.1 . . ?
C00M C00B C00H 116.40(16) . . ?
C00D C00C H00C 119.7 . . ?
C00I C00C H00C 119.7 . . ?
C00I C00C C00D 120.51(19) . . ?
C009 C00D C00C 118.02(19) . . ?
C009 C00D C00G 120.70(19) . . ?
C00C C00D C00G 121.28(18) . . ?
C009 C00E C006 118.01(18) . . ?
C00A C00E C006 122.26(18) . . ?
C00A C00E C009 119.71(19) . . ?
H00A C00F H00D 107.8 . . ?
C00M C00F H00A 109.0 . . ?
C00M C00F H00D 109.0 . . ?
C00P C00F H00A 109.0 . . ?
C00P C00F H00D 109.0 . . ?
C00P C00F C00M 113.12(17) . . ?
C00D C00G H00G 107.7 . . ?
C00D C00G C00N 111.45(18) . . ?
C00D C00G C00O 111.31(19) . . ?
C00N C00G H00G 107.7 . . ?
C00N C00G C00O 110.9(2) . . ?
C00O C00G H00G 107.7 . . ?
C00A C00H C00B 108.03(16) . . ?
C00A C00H C00J 110.71(17) . . ?
C00A C00H C00L 106.20(16) . . ?
C00J C00H C00B 106.83(16) . . ?
C00L C00H C00B 116.03(17) . . ?
C00L C00H C00J 109.05(17) . . ?
C00A C00I H00I 119.2 . . ?
C00C C00I C00A 121.65(19) . . ?
C00C C00I H00I 119.2 . . ?
C00H C00J H00E 109.3 . . ?
C00H C00J H00F 109.3 . . ?
H00E C00J H00F 108.0 . . ?
C00P C00J C00H 111.64(18) . . ?
C00P C00J H00E 109.3 . . ?
C00P C00J H00F 109.3 . . ?
H00H C00K H00J 109.5 . . ?
H00H C00K H00K 109.5 . . ?
H00J C00K H00K 109.5 . . ?
C00M C00K H00H 109.5 . . ?
C00M C00K H00J 109.5 . . ?
C00M C00K H00K 109.5 . . ?
C00H C00L H00L 109.5 . . ?
C00H C00L H00M 109.5 . . ?
C00H C00L H00N 109.5 . . ?
H00L C00L H00M 109.5 . . ?
H00L C00L H00N 109.5 . . ?
H00M C00L H00N 109.5 . . ?
C007 C00M C00B 106.87(17) . . ?
C007 C00M C00F 103.69(17) . . ?
C00B C00M C00F 108.09(17) . . ?
C00K C00M C007 111.47(19) . . ?
C00K C00M C00B 114.64(17) . . ?
C00K C00M C00F 111.40(19) . . ?
C00G C00N H00O 109.5 . . ?
C00G C00N H00P 109.5 . . ?
C00G C00N H00Q 109.5 . . ?
H00O C00N H00P 109.5 . . ?
H00O C00N H00Q 109.5 . . ?
H00P C00N H00Q 109.5 . . ?
C00G C00O H00R 109.5 . . ?
C00G C00O H00S 109.5 . . ?
C00G C00O H00T 109.5 . . ?
H00R C00O H00S 109.5 . . ?
H00R C00O H00T 109.5 . . ?
H00S C00O H00T 109.5 . . ?
C00F C00P C00J 111.13(18) . . ?
C00F C00P H00U 109.4 . . ?
C00F C00P H00V 109.4 . . ?
C00J C00P H00U 109.4 . . ?
C00J C00P H00V 109.4 . . ?
H00U C00P H00V 108.0 . . ?
O005 C00Q H00Z 109.5 . . ?
O005 C00Q H 109.5 . . ?
O005 C00Q HA 109.5 . . ?
H00Z C00Q H 109.5 . . ?
H00Z C00Q HA 109.5 . . ?
H C00Q HA 109.5 . . ?
O004 C00R H00W 109.5 . . ?
O004 C00R H00X 109.5 . . ?
O004 C00R H00Y 109.5 . . ?
H00W C00R H00X 109.5 . . ?
H00W C00R H00Y 109.5 . . ?
H00X C00R H00Y 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
O001 C006 C008 O002 -62.4(2) . . . . ?
O001 C006 C008 C00B 176.89(16) . . . . ?
O001 C006 C00E C009 36.8(3) . . . . ?
O001 C006 C00E C00A -145.02(19) . . . . ?
O002 C008 C00B C00H 169.21(16) . . . . ?
O002 C008 C00B C00M 36.5(2) . . . . ?
O003 C007 C00M C00B -43.7(3) . . . . ?
O003 C007 C00M C00F 70.4(3) . . . . ?
O003 C007 C00M C00K -169.7(2) . . . . ?
O004 C007 C00M C00B 141.14(17) . . . . ?
O004 C007 C00M C00F -104.8(2) . . . . ?
O004 C007 C00M C00K 15.2(3) . . . . ?
C006 C008 C00B C00H -70.8(2) . . . . ?
C006 C008 C00B C00M 156.46(17) . . . . ?
C008 C006 C00E C009 162.01(18) . . . . ?
C008 C006 C00E C00A -19.8(3) . . . . ?
C008 C00B C00H C00A 53.7(2) . . . . ?
C008 C00B C00H C00J 172.79(17) . . . . ?
C008 C00B C00H C00L -65.4(2) . . . . ?
C008 C00B C00M C007 -66.7(2) . . . . ?
C008 C00B C00M C00F -177.74(18) . . . . ?
C008 C00B C00M C00K 57.4(2) . . . . ?
C009 C00D C00G C00N 112.0(2) . . . . ?
C009 C00D C00G C00O -123.6(2) . . . . ?
C00A C00H C00J C00P 174.05(18) . . . . ?
C00B C00H C00J C00P 56.7(2) . . . . ?
C00C C00D C00G C00N -66.9(3) . . . . ?
C00C C00D C00G C00O 57.5(3) . . . . ?
C00D C009 C00E C006 -179.45(19) . . . . ?
C00D C009 C00E C00A 2.3(3) . . . . ?
C00D C00C C00I C00A 0.1(3) . . . . ?
C00E C006 C008 O002 171.57(16) . . . . ?
C00E C006 C008 C00B 50.9(2) . . . . ?
C00E C009 C00D C00C -0.8(3) . . . . ?
C00E C009 C00D C00G -179.7(2) . . . . ?
C00E C00A C00H C00B -21.6(3) . . . . ?
C00E C00A C00H C00J -138.3(2) . . . . ?
C00E C00A C00H C00L 103.5(2) . . . . ?
C00E C00A C00I C00C 1.4(3) . . . . ?
C00H C00A C00E C006 5.1(3) . . . . ?
C00H C00A C00E C009 -176.70(18) . . . . ?
C00H C00A C00I C00C 175.7(2) . . . . ?
C00H C00B C00M C007 163.86(17) . . . . ?
C00H C00B C00M C00F 52.8(2) . . . . ?
C00H C00B C00M C00K -72.1(2) . . . . ?
C00H C00J C00P C00F -59.6(3) . . . . ?
C00I C00A C00E C006 179.33(19) . . . . ?
C00I C00A C00E C009 -2.5(3) . . . . ?
C00I C00A C00H C00B 164.24(18) . . . . ?
C00I C00A C00H C00J 47.6(3) . . . . ?
C00I C00A C00H C00L -70.6(2) . . . . ?
C00I C00C C00D C009 -0.4(3) . . . . ?
C00I C00C C00D C00G 178.5(2) . . . . ?
C00L C00H C00J C00P -69.5(2) . . . . ?
C00M C00B C00H C00A -174.76(17) . . . . ?
C00M C00B C00H C00J -55.6(2) . . . . ?
C00M C00B C00H C00L 66.2(2) . . . . ?
C00M C00F C00P C00J 56.7(3) . . . . ?
C00P C00F C00M C007 -164.59(19) . . . . ?
C00P C00F C00M C00B -51.4(2) . . . . ?
C00P C00F C00M C00K 75.4(2) . . . . ?
C00R O004 C007 O003 4.9(3) . . . . ?
C00R O004 C007 C00M -179.87(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.987
_oxdiff_exptl_absorpt_empirical_full_min 0.266
