# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_p16_collect
_audit_block_doi                 10.5517/ccdc.csd.cc2d9ysg
_database_code_depnum_ccdc_archive 'CCDC 2214106'
loop_
_audit_author_name
_audit_author_address
'weihao chen'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-10-20 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
_audit_creation_date             2021-03-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 O5'
_chemical_formula_sum            'C18 H20 O5'
_chemical_formula_weight         316.34
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C72 H80 O20 '
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                   5.4408(6)
_cell_length_b                   10.6295(14)
_cell_length_c                   26.948(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1558.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2116
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.2900
_cell_measurement_theta_min      5.3010
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
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    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0862
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7480
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.246
_diffrn_reflns_theta_min         3.280
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00 -43.00   0.50    3.00    --    0.00 -19.00 -60.00   74
  2  ω    -10.00  30.00   0.50    3.00    --    0.00 -82.00-150.00   80
  3  ω    -40.00  14.00   0.50    3.00    --    0.00 -19.00 -60.00  108
  4  ω     11.00 109.00   0.50   20.50    --   95.80 -30.00-120.00  196
  5  ω     10.00  73.00   0.50   20.50    --   95.80 -77.00   0.00  126
  6  ω     96.00 131.00   0.50   20.50    --   95.80  82.00 -90.00   70
  7  ω      6.00  92.00   0.50   20.50    --   95.80 -61.00 150.00  172
  8  ω      8.00 110.00   0.50   20.50    --   95.80 -45.00-150.00  204
  9  ω      8.00 124.00   0.50   20.50    --   95.80 -82.00 150.00  232
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1655413000
_diffrn_orient_matrix_UB_12      0.0849037000
_diffrn_orient_matrix_UB_13      -0.0320820000
_diffrn_orient_matrix_UB_21      -0.2206754000
_diffrn_orient_matrix_UB_22      -0.0314661000
_diffrn_orient_matrix_UB_23      0.0335309000
_diffrn_orient_matrix_UB_31      0.0631090000
_diffrn_orient_matrix_UB_32      0.1132130000
_diffrn_orient_matrix_UB_33      0.0334137000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_reflns_Friedel_coverage         0.663
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                2264
_reflns_number_total             3064
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details 
;
 Flack x determined using 699 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0784
_refine_ls_restrained_S_all      1.107
_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)+(0.1195P)²+2.3705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2248
_refine_ls_wR_factor_ref         0.2448
_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:
 C7(H7), C15(H15), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C18(H18A,H18B,H18C), C17(H17A,H17B,
 H17C)
;
_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 0.1601(9) 0.1131(4) 0.42868(17) 0.0258(11) Uani 1 1 d . . . . .
O1 O 0.9252(9) 0.2698(5) 0.28010(17) 0.0277(11) Uani 1 1 d . . . . .
O4 O 0.0479(10) 0.2877(5) 0.46918(18) 0.0332(12) Uani 1 1 d . . . . .
O2 O 0.0910(10) -0.0875(5) 0.36264(19) 0.0327(12) Uani 1 1 d . . . . .
O5 O 0.1460(10) 0.4488(5) 0.3685(2) 0.0362(13) Uani 1 1 d . . . . .
C8 C 0.5978(14) 0.1908(6) 0.3288(2) 0.0249(14) Uani 1 1 d . . . . .
C2 C 0.9137(14) 0.1649(6) 0.2503(2) 0.0256(14) Uani 1 1 d . . . . .
C1 C 0.7566(13) 0.2801(7) 0.3177(2) 0.0260(15) Uani 1 1 d . . . . .
H1 H 0.7544 0.3538 0.3364 0.031 Uiso 1 1 calc R U . . .
C7 C 0.3939(13) 0.2034(6) 0.3663(2) 0.0230(14) Uani 1 1 d . . . . .
H7 H 0.2441 0.2191 0.3471 0.028 Uiso 1 1 calc R U . . .
C10 C 0.1852(14) 0.2385(7) 0.4399(2) 0.0284(16) Uani 1 1 d . . . . .
C6 C 0.3517(13) 0.0795(7) 0.3932(2) 0.0240(14) Uani 1 1 d . . . . .
C12 C 0.3262(14) 0.4323(7) 0.3941(2) 0.0258(15) Uani 1 1 d . . . . .
C15 C 0.4900(13) 0.5369(6) 0.4115(3) 0.0274(15) Uani 1 1 d . . . . .
H15 H 0.6604 0.5126 0.4047 0.033 Uiso 1 1 calc R U . . .
C14 C 0.5702(14) 0.0271(7) 0.4214(3) 0.0293(15) Uani 1 1 d . . . . .
H14A H 0.6164 0.0848 0.4472 0.044 Uiso 1 1 calc R U . . .
H14B H 0.7058 0.0158 0.3991 0.044 Uiso 1 1 calc R U . . .
H14C H 0.5269 -0.0524 0.4359 0.044 Uiso 1 1 calc R U . . .
C11 C 0.3890(14) 0.2975(6) 0.4093(2) 0.0254(14) Uani 1 1 d . . . . .
H11 H 0.5447 0.2954 0.4276 0.031 Uiso 1 1 calc R U . . .
C5 C 0.2627(14) -0.0161(7) 0.3545(3) 0.0278(16) Uani 1 1 d . . . . .
C9 C 0.5820(13) 0.0752(6) 0.2997(2) 0.0246(14) Uani 1 1 d . . . . .
C16 C 0.4600(15) 0.5484(6) 0.4679(3) 0.0309(16) Uani 1 1 d . . . . .
H16A H 0.2949 0.5774 0.4752 0.037 Uiso 1 1 calc R U . . .
H16B H 0.4797 0.4659 0.4828 0.037 Uiso 1 1 calc R U . . .
C3 C 0.7542(14) 0.0711(7) 0.2591(3) 0.0291(16) Uani 1 1 d . . . . .
H3 H 0.7548 0.0013 0.2383 0.035 Uiso 1 1 calc R U . . .
C13 C 1.1028(15) 0.1704(7) 0.2105(3) 0.0315(16) Uani 1 1 d . . . . .
H13A H 1.0800 0.2454 0.1912 0.047 Uiso 1 1 calc R U . . .
H13B H 1.0869 0.0981 0.1894 0.047 Uiso 1 1 calc R U . . .
H13C H 1.2635 0.1712 0.2251 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4165(14) -0.0167(7) 0.3102(3) 0.0286(15) Uani 1 1 d . . . . .
H4 H 0.4003 -0.0832 0.2880 0.034 Uiso 1 1 calc R U . . .
C18 C 0.4389(17) 0.6585(7) 0.3842(3) 0.0341(17) Uani 1 1 d . . . . .
H18A H 0.4390 0.6431 0.3491 0.051 Uiso 1 1 calc R U . . .
H18B H 0.5638 0.7190 0.3922 0.051 Uiso 1 1 calc R U . . .
H18C H 0.2813 0.6906 0.3941 0.051 Uiso 1 1 calc R U . . .
C17 C 0.6428(16) 0.6380(8) 0.4912(3) 0.0395(19) Uani 1 1 d . . . . .
H17A H 0.6146 0.7215 0.4789 0.059 Uiso 1 1 calc R U . . .
H17B H 0.8067 0.6120 0.4829 0.059 Uiso 1 1 calc R U . . .
H17C H 0.6230 0.6372 0.5266 0.059 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
O3 C10 1.373(9) . ?
O3 C6 1.459(8) . ?
O1 C2 1.376(8) . ?
O1 C1 1.372(8) . ?
O4 C10 1.206(8) . ?
O2 C5 1.223(9) . ?
O5 C12 1.212(8) . ?
C8 C1 1.318(10) . ?
C8 C7 1.505(9) . ?
C8 C9 1.461(9) . ?
C2 C3 1.343(10) . ?
C2 C13 1.487(10) . ?
C1 H1 0.9300 . ?
C7 H7 0.9800 . ?
C7 C6 1.522(9) . ?
C7 C11 1.532(9) . ?
C10 C11 1.518(10) . ?
C6 C14 1.516(10) . ?
C6 C5 1.534(10) . ?
C12 C15 1.500(10) . ?
C12 C11 1.529(9) . ?
C15 H15 0.9800 . ?
C15 C16 1.534(10) . ?
C15 C18 1.513(10) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C11 H11 0.9800 . ?
C5 C4 1.460(10) . ?
C9 C3 1.441(10) . ?
C9 C4 1.358(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.512(11) . ?
C3 H3 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C4 H4 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C10 O3 C6 108.1(5) . . ?
C1 O1 C2 117.8(5) . . ?
C1 C8 C7 124.8(6) . . ?
C1 C8 C9 121.5(6) . . ?
C9 C8 C7 113.1(6) . . ?
O1 C2 C13 111.0(6) . . ?
C3 C2 O1 121.8(6) . . ?
C3 C2 C13 127.2(6) . . ?
O1 C1 H1 118.4 . . ?
C8 C1 O1 123.2(6) . . ?
C8 C1 H1 118.4 . . ?
C8 C7 H7 105.9 . . ?
C8 C7 C6 110.7(5) . . ?
C8 C7 C11 125.3(6) . . ?
C6 C7 H7 105.9 . . ?
C6 C7 C11 101.6(5) . . ?
C11 C7 H7 105.9 . . ?
O3 C10 C11 110.8(6) . . ?
O4 C10 O3 120.2(7) . . ?
O4 C10 C11 128.9(7) . . ?
O3 C6 C7 102.0(5) . . ?
O3 C6 C14 108.8(5) . . ?
O3 C6 C5 112.4(6) . . ?
C7 C6 C5 107.3(5) . . ?
C14 C6 C7 116.0(6) . . ?
C14 C6 C5 110.2(6) . . ?
O5 C12 C15 123.5(7) . . ?
O5 C12 C11 118.0(6) . . ?
C15 C12 C11 118.5(6) . . ?
C12 C15 H15 107.9 . . ?
C12 C15 C16 107.8(6) . . ?
C12 C15 C18 111.8(6) . . ?
C16 C15 H15 107.9 . . ?
C18 C15 H15 107.9 . . ?
C18 C15 C16 113.2(6) . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C11 H11 110.5 . . ?
C10 C11 C7 98.8(5) . . ?
C10 C11 C12 111.7(6) . . ?
C10 C11 H11 110.5 . . ?
C12 C11 C7 114.4(5) . . ?
C12 C11 H11 110.5 . . ?
O2 C5 C6 122.1(6) . . ?
O2 C5 C4 125.5(7) . . ?
C4 C5 C6 112.2(6) . . ?
C3 C9 C8 113.3(6) . . ?
C4 C9 C8 122.2(6) . . ?
C4 C9 C3 124.5(6) . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 C15 113.0(7) . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C2 C3 C9 122.2(7) . . ?
C2 C3 H3 118.9 . . ?
C9 C3 H3 118.9 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C4 H4 118.4 . . ?
C9 C4 C5 123.2(7) . . ?
C9 C4 H4 118.4 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O3 C10 C11 C7 22.6(7) . . . . ?
O3 C10 C11 C12 143.3(6) . . . . ?
O3 C6 C5 O2 -24.4(9) . . . . ?
O3 C6 C5 C4 159.8(6) . . . . ?
O1 C2 C3 C9 1.2(11) . . . . ?
O4 C10 C11 C7 -154.4(8) . . . . ?
O4 C10 C11 C12 -33.7(10) . . . . ?
O2 C5 C4 C9 170.4(7) . . . . ?
O5 C12 C15 C16 112.0(8) . . . . ?
O5 C12 C15 C18 -13.0(10) . . . . ?
O5 C12 C11 C7 50.1(9) . . . . ?
O5 C12 C11 C10 -61.1(8) . . . . ?
C8 C7 C6 O3 177.3(5) . . . . ?
C8 C7 C6 C14 59.3(7) . . . . ?
C8 C7 C6 C5 -64.3(7) . . . . ?
C8 C7 C11 C10 -164.5(6) . . . . ?
C8 C7 C11 C12 76.7(8) . . . . ?
C8 C9 C3 C2 1.0(10) . . . . ?
C8 C9 C4 C5 -8.1(11) . . . . ?
C2 O1 C1 C8 5.2(9) . . . . ?
C1 O1 C2 C3 -4.2(9) . . . . ?
C1 O1 C2 C13 178.1(6) . . . . ?
C1 C8 C7 C6 -144.9(7) . . . . ?
C1 C8 C7 C11 -22.7(10) . . . . ?
C1 C8 C9 C3 0.0(10) . . . . ?
C1 C8 C9 C4 -178.9(7) . . . . ?
C7 C8 C1 O1 -173.5(6) . . . . ?
C7 C8 C9 C3 171.4(6) . . . . ?
C7 C8 C9 C4 -7.4(9) . . . . ?
C7 C6 C5 O2 -135.8(7) . . . . ?
C7 C6 C5 C4 48.5(8) . . . . ?
C10 O3 C6 C7 -28.8(7) . . . . ?
C10 O3 C6 C14 94.3(6) . . . . ?
C10 O3 C6 C5 -143.4(6) . . . . ?
C6 O3 C10 O4 -179.1(6) . . . . ?
C6 O3 C10 C11 3.7(7) . . . . ?
C6 C7 C11 C10 -38.4(6) . . . . ?
C6 C7 C11 C12 -157.2(6) . . . . ?
C6 C5 C4 C9 -14.0(10) . . . . ?
C12 C15 C16 C17 171.6(6) . . . . ?
C15 C12 C11 C7 -129.9(6) . . . . ?
C15 C12 C11 C10 118.9(7) . . . . ?
C14 C6 C5 O2 97.1(8) . . . . ?
C14 C6 C5 C4 -78.7(7) . . . . ?
C11 C7 C6 O3 42.2(6) . . . . ?
C11 C7 C6 C14 -75.9(7) . . . . ?
C11 C7 C6 C5 160.5(6) . . . . ?
C11 C12 C15 C16 -68.0(8) . . . . ?
C11 C12 C15 C18 167.0(6) . . . . ?
C9 C8 C1 O1 -3.1(11) . . . . ?
C9 C8 C7 C6 43.9(7) . . . . ?
C9 C8 C7 C11 166.1(6) . . . . ?
C3 C9 C4 C5 173.2(7) . . . . ?
C13 C2 C3 C9 178.5(7) . . . . ?
C4 C9 C3 C2 179.7(7) . . . . ?
C18 C15 C16 C17 -64.1(9) . . . . ?

_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 1.688
_oxdiff_exptl_absorpt_empirical_full_min 0.719
####################################################################### 
# 
# 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_chenweihao_l-p18_collect
_audit_block_doi                 10.5517/ccdc.csd.cc2d9yth
_database_code_depnum_ccdc_archive 'CCDC 2214107'
loop_
_audit_author_name
_audit_author_address
'weihao chen'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-10-20 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
_audit_creation_date             2021-03-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C17 H22 O4)'
_chemical_formula_sum            'C34 H44 O8'
_chemical_formula_weight         580.69
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C70 H90 O14 '
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                   5.6306(2)
_cell_length_b                   22.6115(8)
_cell_length_c                   12.1140(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.781(4)
_cell_angle_gamma                90
_cell_volume                     1538.95(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6171
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.9520
_cell_measurement_theta_min      3.9460
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.870
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
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    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15141
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.349
_diffrn_reflns_theta_min         3.657
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  29.00   0.50    1.00    --    0.00 -77.00 150.00  148
  2  ω    -12.00  13.00   0.50    1.00    --    0.00  38.00 -90.00   50
  3  ω     31.00  87.00   0.50    1.00    --    0.00  38.00 -90.00  112
  4  ω      2.00  30.00   0.50    1.00    --    0.00 -82.00  90.00   56
  5  ω     32.00  86.00   0.50    1.00    --    0.00  38.00 -30.00  108
  6  ω    -33.00   7.00   0.50    1.00    --    0.00 -82.00 -90.00   80
  7  ω     73.00 124.00   0.50    8.00    --   95.80  61.00 -60.00  102
  8  ω     80.00 183.00   0.50    8.00    --   95.80  45.00-180.00  206
  9  ω     19.00 103.00   0.50    8.00    --   95.80 -77.00 150.00  168
 10  ω     10.00  48.00   0.50    8.00    --   95.80 -30.00-120.00   76
 11  ω     59.00 111.00   0.50    8.00    --   95.80 -30.00-120.00  104
 12  ω     37.00 118.00   0.50    8.00    --   95.80 -61.00 -30.00  162
 13  ω    105.00 183.00   0.50    8.00    --   95.80  77.00 -60.00  156
 14  ω     58.00  94.00   0.50    8.00    --   95.80 -77.00 -30.00   72
 15  ω     69.00 106.00   0.50    8.00    --   95.80 -30.00 150.00   74
 16  ω     87.00 173.00   0.50    8.00    --   95.80  30.00 150.00  172
 17  ω      8.00 115.00   0.50    8.00    --   95.80 -61.00-150.00  214
 18  ω     59.00 105.00   0.50    8.00    --   95.80 -77.00-120.00   92
 19  ω      8.00  35.00   0.50    8.00    --   95.80 -77.00 -30.00   54
 20  ω     73.00 132.00   0.50    8.00    --   95.80  61.00 -30.00  118
 21  ω    157.00 184.00   0.50    8.00    --   95.80  61.00 -30.00   54
 22  ω     90.00 115.00   0.50    8.00    --   95.80  82.00  60.00   50
 23  ω    136.00 161.00   0.50    8.00    --   95.80  82.00  60.00   50
 24  ω    120.00 178.00   0.50    8.00    --   95.80   0.00 120.00  116
 25  ω     26.00  63.00   0.50    8.00    --   95.80   0.00 120.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0438456000
_diffrn_orient_matrix_UB_12      0.0408944000
_diffrn_orient_matrix_UB_13      0.0982798000
_diffrn_orient_matrix_UB_21      -0.1766490000
_diffrn_orient_matrix_UB_22      -0.0453711000
_diffrn_orient_matrix_UB_23      0.0426801000
_diffrn_orient_matrix_UB_31      0.2049934000
_diffrn_orient_matrix_UB_32      -0.0302053000
_diffrn_orient_matrix_UB_33      0.0690367000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                5422
_reflns_number_total             5999
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 2304 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         5999
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0613
_refine_ls_restrained_S_all      1.040
_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)+(0.1165P)²+0.4546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.1740
_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:
 C14'(H14'), C7(H7), C7'(H7'), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10C,H10D), C10'(H10A,H10B), C15'(H15A,H15B), C15(H15C,H15D)
2.c Aromatic/amide H refined with riding coordinates:
 C4'(H4'), C3'(H3'A), C4(H4), C3(H3), C1'(H1'), C1(H1)
2.d Idealised Me refined as rotating group:
 C12(H12D,H12E,H12F), C11(H11D,H11E,H11F), C12'(H12A,H12B,H12C), C16'(H16A,
 H16B,H16C), C11'(H11A,H11B,H11C), C17'(H17A,H17B,H17C), C17(H17D,H17E,H17F),
 C16(H16D,H16E,H16F)
2.e Idealised tetrahedral OH refined as rotating group:
 O3'(H3')
;
_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 0.5321(6) 0.64626(14) 0.9196(3) 0.0309(7) Uani 1 1 d . . . . .
O2 O 0.2153(5) 0.47173(15) 0.3919(3) 0.0310(7) Uani 1 1 d . . . . .
O3 O 0.1332(5) 0.50420(14) 0.5932(3) 0.0302(7) Uani 1 1 d . . . . .
O4 O 1.0566(5) 0.34746(13) 0.6364(3) 0.0282(6) Uani 1 1 d . . . . .
O1 O 0.5235(6) 0.29268(13) 0.3606(3) 0.0339(7) Uani 1 1 d . . . . .
O4' O 0.0174(7) 0.69792(15) 1.1935(3) 0.0400(8) Uani 1 1 d . . . . .
O2' O -0.3540(5) 0.48122(15) 0.9666(3) 0.0339(7) Uani 1 1 d . . . . .
O3' O -0.2226(5) 0.51793(15) 1.1678(3) 0.0322(7) Uani 1 1 d . . . . .
H3' H -0.3258 0.4943 1.1458 0.048 Uiso 1 1 calc R U . . .
C9' C 0.1325(7) 0.57214(18) 0.8924(3) 0.0256(8) Uani 1 1 d . . . . .
C5 C 0.3217(7) 0.47656(18) 0.5873(4) 0.0257(8) Uani 1 1 d . . . . .
C4' C -0.0572(8) 0.53421(19) 0.8790(4) 0.0280(9) Uani 1 1 d . . . . .
H4' H -0.1127 0.5229 0.8082 0.034 Uiso 1 1 calc R U . . .
C5' C -0.1706(7) 0.51191(19) 0.9725(4) 0.0270(9) Uani 1 1 d . . . . .
C13 C 0.6260(8) 0.3312(2) 0.3132(4) 0.0305(9) Uani 1 1 d . . . . .
C2' C 0.4578(8) 0.62571(19) 0.8172(4) 0.0294(9) Uani 1 1 d . . . . .
C8' C 0.2093(7) 0.59666(17) 0.9990(3) 0.0249(8) Uani 1 1 d . . . . .
C9 C 0.6547(7) 0.41817(18) 0.6659(3) 0.0238(8) Uani 1 1 d . . . . .
C3' C 0.2657(8) 0.59110(19) 0.8019(4) 0.0286(9) Uani 1 1 d . . . . .
H3'A H 0.2172 0.5790 0.7306 0.034 Uiso 1 1 calc R U . . .
C2 C 1.0042(7) 0.36497(19) 0.7398(4) 0.0257(8) Uani 1 1 d . . . . .
C8 C 0.7048(7) 0.39476(17) 0.5589(3) 0.0236(8) Uani 1 1 d . . . . .
C4 C 0.4665(7) 0.45507(18) 0.6805(4) 0.0255(8) Uani 1 1 d . . . . .
H4 H 0.4323 0.4663 0.7516 0.031 Uiso 1 1 calc R U . . .
C14' C 0.2933(8) 0.68254(19) 1.3499(4) 0.0286(9) Uani 1 1 d . . . . .
H14' H 0.3905 0.6492 1.3784 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4135(7) 0.46756(18) 0.4722(4) 0.0251(8) Uani 1 1 d . . . . .
C13' C 0.1503(8) 0.66345(19) 1.2449(4) 0.0271(9) Uani 1 1 d . . . . .
C3 C 0.8145(7) 0.39848(18) 0.7569(4) 0.0259(8) Uani 1 1 d . . . . .
H3 H 0.7847 0.4094 0.8287 0.031 Uiso 1 1 calc R U . . .
C7 C 0.5244(7) 0.40622(18) 0.4621(4) 0.0254(8) Uani 1 1 d . . . . .
H7 H 0.3953 0.3777 0.4693 0.030 Uiso 1 1 calc R U . . .
C1' C 0.4015(8) 0.63212(19) 1.0067(4) 0.0286(9) Uani 1 1 d . . . . .
H1' H 0.4481 0.6480 1.0756 0.034 Uiso 1 1 calc R U . . .
C1 C 0.8979(7) 0.36198(19) 0.5498(4) 0.0265(8) Uani 1 1 d . . . . .
H1 H 0.9278 0.3479 0.4800 0.032 Uiso 1 1 calc R U . . .
C7' C 0.0541(7) 0.58592(19) 1.0951(4) 0.0268(9) Uani 1 1 d . . . . .
H7' H -0.0812 0.6130 1.0847 0.032 Uiso 1 1 calc R U . . .
C12 C 0.5890(8) 0.51781(19) 0.4529(4) 0.0282(9) Uani 1 1 d . . . . .
H12D H 0.6343 0.5164 0.3779 0.042 Uiso 1 1 calc R U . . .
H12E H 0.7280 0.5134 0.5025 0.042 Uiso 1 1 calc R U . . .
H12F H 0.5148 0.5551 0.4661 0.042 Uiso 1 1 calc R U . . .
C10 C 0.6188(8) 0.39552(19) 0.3487(4) 0.0280(9) Uani 1 1 d . . . . .
H10C H 0.5201 0.4173 0.2940 0.034 Uiso 1 1 calc R U . . .
H10D H 0.7786 0.4116 0.3488 0.034 Uiso 1 1 calc R U . . .
C6' C -0.0496(7) 0.52293(19) 1.0877(3) 0.0263(8) Uani 1 1 d . . . . .
C10' C 0.1746(8) 0.59986(19) 1.2085(3) 0.0274(8) Uani 1 1 d . . . . .
H10A H 0.1076 0.5744 1.2629 0.033 Uiso 1 1 calc R U . . .
H10B H 0.3426 0.5904 1.2075 0.033 Uiso 1 1 calc R U . . .
C11 C 1.1827(8) 0.3424(2) 0.8265(4) 0.0312(9) Uani 1 1 d . . . . .
H11D H 1.1621 0.3006 0.8354 0.047 Uiso 1 1 calc R U . . .
H11E H 1.1604 0.3620 0.8954 0.047 Uiso 1 1 calc R U . . .
H11F H 1.3404 0.3503 0.8045 0.047 Uiso 1 1 calc R U . . .
C12' C 0.1394(8) 0.4745(2) 1.1087(4) 0.0285(9) Uani 1 1 d . . . . .
H12A H 0.2056 0.4771 1.1836 0.043 Uiso 1 1 calc R U . . .
H12B H 0.2635 0.4798 1.0589 0.043 Uiso 1 1 calc R U . . .
H12C H 0.0673 0.4364 1.0966 0.043 Uiso 1 1 calc R U . . .
C15' C 0.1210(9) 0.7010(2) 1.4375(4) 0.0330(9) Uani 1 1 d . . . . .
H15A H 0.2128 0.7161 1.5020 0.040 Uiso 1 1 calc R U . . .
H15B H 0.0208 0.7329 1.4078 0.040 Uiso 1 1 calc R U . . .
C16' C -0.0367(10) 0.6511(2) 1.4732(4) 0.0401(11) Uani 1 1 d . . . . .
H16A H -0.1391 0.6383 1.4113 0.060 Uiso 1 1 calc R U . . .
H16B H -0.1315 0.6647 1.5312 0.060 Uiso 1 1 calc R U . . .
H16C H 0.0608 0.6186 1.4998 0.060 Uiso 1 1 calc R U . . .
C11' C 0.6115(9) 0.6465(2) 0.7297(4) 0.0343(10) Uani 1 1 d . . . . .
H11A H 0.5843 0.6879 0.7164 0.051 Uiso 1 1 calc R U . . .
H11B H 0.5737 0.6247 0.6627 0.051 Uiso 1 1 calc R U . . .
H11C H 0.7756 0.6402 0.7534 0.051 Uiso 1 1 calc R U . . .
C17' C 0.4565(9) 0.7338(2) 1.3231(5) 0.0373(11) Uani 1 1 d . . . . .
H17A H 0.5654 0.7211 1.2702 0.056 Uiso 1 1 calc R U . . .
H17B H 0.5444 0.7465 1.3895 0.056 Uiso 1 1 calc R U . . .
H17C H 0.3625 0.7661 1.2928 0.056 Uiso 1 1 calc R U . . .
C14 C 0.7616(9) 0.3176(2) 0.2119(4) 0.0387(11) Uani 1 1 d . . . . .
H14 H 0.8518 0.3526 0.1919 0.046 Uiso 1 1 calc R U . . .
C15 C 0.5838(10) 0.3010(3) 0.1157(4) 0.0431(12) Uani 1 1 d . . . . .
H15C H 0.5042 0.2646 0.1339 0.052 Uiso 1 1 calc R U . . .
H15D H 0.4637 0.3318 0.1071 0.052 Uiso 1 1 calc R U . . .
C17 C 0.9360(10) 0.2658(3) 0.2394(5) 0.0508(14) Uani 1 1 d . . . . .
H17D H 1.0459 0.2770 0.2998 0.076 Uiso 1 1 calc R U . . .
H17E H 1.0222 0.2569 0.1757 0.076 Uiso 1 1 calc R U . . .
H17F H 0.8480 0.2316 0.2597 0.076 Uiso 1 1 calc R U . . .
C16 C 0.6960(15) 0.2929(3) 0.0065(5) 0.0615(17) Uani 1 1 d . . . . .
H16D H 0.5756 0.2821 -0.0496 0.092 Uiso 1 1 calc R U . . .
H16E H 0.8139 0.2622 0.0138 0.092 Uiso 1 1 calc R U . . .
H16F H 0.7699 0.3292 -0.0138 0.092 Uiso 1 1 calc R U . . .
H2 H 0.120(12) 0.487(3) 0.440(6) 0.045(17) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1' C2' 1.365(6) . ?
O1' C1' 1.363(5) . ?
O2 C6 1.435(5) . ?
O2 H2 0.89(7) . ?
O3 C5 1.238(5) . ?
O4 C2 1.365(5) . ?
O4 C1 1.372(5) . ?
O1 C13 1.211(6) . ?
O4' C13' 1.222(5) . ?
O2' C5' 1.242(5) . ?
O3' H3' 0.8200 . ?
O3' C6' 1.424(5) . ?
C9' C4' 1.371(6) . ?
C9' C8' 1.445(6) . ?
C9' C3' 1.434(6) . ?
C5 C4 1.433(6) . ?
C5 C6 1.532(6) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.429(6) . ?
C5' C6' 1.533(6) . ?
C13 C10 1.517(6) . ?
C13 C14 1.519(6) . ?
C2' C3' 1.338(7) . ?
C2' C11' 1.488(6) . ?
C8' C1' 1.345(6) . ?
C8' C7' 1.520(6) . ?
C9 C8 1.445(6) . ?
C9 C4 1.369(6) . ?
C9 C3 1.446(6) . ?
C3' H3'A 0.9300 . ?
C2 C3 1.336(6) . ?
C2 C11 1.495(6) . ?
C8 C7 1.522(6) . ?
C8 C1 1.327(6) . ?
C4 H4 0.9300 . ?
C14' H14' 0.9800 . ?
C14' C13' 1.523(6) . ?
C14' C15' 1.542(6) . ?
C14' C17' 1.528(6) . ?
C6 C7 1.529(6) . ?
C6 C12 1.534(6) . ?
C13' C10' 1.513(6) . ?
C3 H3 0.9300 . ?
C7 H7 0.9800 . ?
C7 C10 1.525(6) . ?
C1' H1' 0.9300 . ?
C1 H1 0.9300 . ?
C7' H7' 0.9800 . ?
C7' C6' 1.540(6) . ?
C7' C10' 1.524(6) . ?
C12 H12D 0.9600 . ?
C12 H12E 0.9600 . ?
C12 H12F 0.9600 . ?
C10 H10C 0.9700 . ?
C10 H10D 0.9700 . ?
C6' C12' 1.536(6) . ?
C10' H10A 0.9700 . ?
C10' H10B 0.9700 . ?
C11 H11D 0.9600 . ?
C11 H11E 0.9600 . ?
C11 H11F 0.9600 . ?
C12' H12A 0.9600 . ?
C12' H12B 0.9600 . ?
C12' H12C 0.9600 . ?
C15' H15A 0.9700 . ?
C15' H15B 0.9700 . ?
C15' C16' 1.518(7) . ?
C16' H16A 0.9600 . ?
C16' H16B 0.9600 . ?
C16' H16C 0.9600 . ?
C11' H11A 0.9600 . ?
C11' H11B 0.9600 . ?
C11' H11C 0.9600 . ?
C17' H17A 0.9600 . ?
C17' H17B 0.9600 . ?
C17' H17C 0.9600 . ?
C14 H14 0.9800 . ?
C14 C15 1.532(7) . ?
C14 C17 1.549(8) . ?
C15 H15C 0.9700 . ?
C15 H15D 0.9700 . ?
C15 C16 1.514(8) . ?
C17 H17D 0.9600 . ?
C17 H17E 0.9600 . ?
C17 H17F 0.9600 . ?
C16 H16D 0.9600 . ?
C16 H16E 0.9600 . ?
C16 H16F 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
C1' O1' C2' 118.4(4) . . ?
C6 O2 H2 93(4) . . ?
C2 O4 C1 117.6(3) . . ?
C6' O3' H3' 109.5 . . ?
C4' C9' C8' 122.0(4) . . ?
C4' C9' C3' 122.7(4) . . ?
C3' C9' C8' 115.3(4) . . ?
O3 C5 C4 124.8(4) . . ?
O3 C5 C6 117.5(4) . . ?
C4 C5 C6 117.6(3) . . ?
C9' C4' H4' 119.6 . . ?
C9' C4' C5' 120.9(4) . . ?
C5' C4' H4' 119.6 . . ?
O2' C5' C4' 124.4(4) . . ?
O2' C5' C6' 117.5(4) . . ?
C4' C5' C6' 118.0(4) . . ?
O1 C13 C10 122.2(4) . . ?
O1 C13 C14 121.1(4) . . ?
C10 C13 C14 116.6(4) . . ?
O1' C2' C11' 112.5(4) . . ?
C3' C2' O1' 121.4(4) . . ?
C3' C2' C11' 126.1(4) . . ?
C9' C8' C7' 118.0(4) . . ?
C1' C8' C9' 118.8(4) . . ?
C1' C8' C7' 122.9(4) . . ?
C8 C9 C3 115.0(4) . . ?
C4 C9 C8 122.5(4) . . ?
C4 C9 C3 122.5(4) . . ?
C9' C3' H3'A 119.1 . . ?
C2' C3' C9' 121.9(4) . . ?
C2' C3' H3'A 119.1 . . ?
O4 C2 C11 111.7(4) . . ?
C3 C2 O4 122.0(4) . . ?
C3 C2 C11 126.3(4) . . ?
C9 C8 C7 118.0(4) . . ?
C1 C8 C9 119.2(4) . . ?
C1 C8 C7 122.7(4) . . ?
C5 C4 H4 119.7 . . ?
C9 C4 C5 120.7(4) . . ?
C9 C4 H4 119.7 . . ?
C13' C14' H14' 109.2 . . ?
C13' C14' C15' 109.2(4) . . ?
C13' C14' C17' 109.3(4) . . ?
C15' C14' H14' 109.2 . . ?
C17' C14' H14' 109.2 . . ?
C17' C14' C15' 110.8(4) . . ?
O2 C6 C5 108.3(3) . . ?
O2 C6 C7 108.0(3) . . ?
O2 C6 C12 109.1(3) . . ?
C5 C6 C12 107.5(3) . . ?
C7 C6 C5 111.0(3) . . ?
C7 C6 C12 112.9(3) . . ?
O4' C13' C14' 121.1(4) . . ?
O4' C13' C10' 121.5(4) . . ?
C10' C13' C14' 117.4(4) . . ?
C9 C3 H3 119.3 . . ?
C2 C3 C9 121.3(4) . . ?
C2 C3 H3 119.3 . . ?
C8 C7 C6 110.4(3) . . ?
C8 C7 H7 106.3 . . ?
C8 C7 C10 114.4(4) . . ?
C6 C7 H7 106.3 . . ?
C10 C7 C6 112.6(3) . . ?
C10 C7 H7 106.3 . . ?
O1' C1' H1' 118.0 . . ?
C8' C1' O1' 124.0(4) . . ?
C8' C1' H1' 118.0 . . ?
O4 C1 H1 117.7 . . ?
C8 C1 O4 124.5(4) . . ?
C8 C1 H1 117.7 . . ?
C8' C7' H7' 106.4 . . ?
C8' C7' C6' 109.8(3) . . ?
C8' C7' C10' 114.4(4) . . ?
C6' C7' H7' 106.4 . . ?
C10' C7' H7' 106.4 . . ?
C10' C7' C6' 112.8(3) . . ?
C6 C12 H12D 109.5 . . ?
C6 C12 H12E 109.5 . . ?
C6 C12 H12F 109.5 . . ?
H12D C12 H12E 109.5 . . ?
H12D C12 H12F 109.5 . . ?
H12E C12 H12F 109.5 . . ?
C13 C10 C7 115.1(3) . . ?
C13 C10 H10C 108.5 . . ?
C13 C10 H10D 108.5 . . ?
C7 C10 H10C 108.5 . . ?
C7 C10 H10D 108.5 . . ?
H10C C10 H10D 107.5 . . ?
O3' C6' C5' 108.9(3) . . ?
O3' C6' C7' 107.9(3) . . ?
O3' C6' C12' 109.2(3) . . ?
C5' C6' C7' 110.3(3) . . ?
C5' C6' C12' 107.2(3) . . ?
C12' C6' C7' 113.2(3) . . ?
C13' C10' C7' 114.5(4) . . ?
C13' C10' H10A 108.6 . . ?
C13' C10' H10B 108.6 . . ?
C7' C10' H10A 108.6 . . ?
C7' C10' H10B 108.6 . . ?
H10A C10' H10B 107.6 . . ?
C2 C11 H11D 109.5 . . ?
C2 C11 H11E 109.5 . . ?
C2 C11 H11F 109.5 . . ?
H11D C11 H11E 109.5 . . ?
H11D C11 H11F 109.5 . . ?
H11E C11 H11F 109.5 . . ?
C6' C12' H12A 109.5 . . ?
C6' C12' H12B 109.5 . . ?
C6' C12' H12C 109.5 . . ?
H12A C12' H12B 109.5 . . ?
H12A C12' H12C 109.5 . . ?
H12B C12' H12C 109.5 . . ?
C14' C15' H15A 108.8 . . ?
C14' C15' H15B 108.8 . . ?
H15A C15' H15B 107.7 . . ?
C16' C15' C14' 113.6(4) . . ?
C16' C15' H15A 108.8 . . ?
C16' C15' H15B 108.8 . . ?
C15' C16' H16A 109.5 . . ?
C15' C16' H16B 109.5 . . ?
C15' C16' H16C 109.5 . . ?
H16A C16' H16B 109.5 . . ?
H16A C16' H16C 109.5 . . ?
H16B C16' H16C 109.5 . . ?
C2' C11' H11A 109.5 . . ?
C2' C11' H11B 109.5 . . ?
C2' C11' H11C 109.5 . . ?
H11A C11' H11B 109.5 . . ?
H11A C11' H11C 109.5 . . ?
H11B C11' H11C 109.5 . . ?
C14' C17' H17A 109.5 . . ?
C14' C17' H17B 109.5 . . ?
C14' C17' H17C 109.5 . . ?
H17A C17' H17B 109.5 . . ?
H17A C17' H17C 109.5 . . ?
H17B C17' H17C 109.5 . . ?
C13 C14 H14 109.4 . . ?
C13 C14 C15 109.1(4) . . ?
C13 C14 C17 109.0(4) . . ?
C15 C14 H14 109.4 . . ?
C15 C14 C17 110.6(4) . . ?
C17 C14 H14 109.4 . . ?
C14 C15 H15C 108.8 . . ?
C14 C15 H15D 108.8 . . ?
H15C C15 H15D 107.7 . . ?
C16 C15 C14 113.9(5) . . ?
C16 C15 H15C 108.8 . . ?
C16 C15 H15D 108.8 . . ?
C14 C17 H17D 109.5 . . ?
C14 C17 H17E 109.5 . . ?
C14 C17 H17F 109.5 . . ?
H17D C17 H17E 109.5 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
C15 C16 H16D 109.5 . . ?
C15 C16 H16E 109.5 . . ?
C15 C16 H16F 109.5 . . ?
H16D C16 H16E 109.5 . . ?
H16D C16 H16F 109.5 . . ?
H16E C16 H16F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1' C2' C3' C9' -2.1(6) . . . . ?
O2 C6 C7 C8 -169.3(3) . . . . ?
O2 C6 C7 C10 61.6(4) . . . . ?
O3 C5 C4 C9 171.1(4) . . . . ?
O3 C5 C6 O2 -23.7(5) . . . . ?
O3 C5 C6 C7 -142.1(4) . . . . ?
O3 C5 C6 C12 94.1(4) . . . . ?
O4 C2 C3 C9 -0.2(6) . . . . ?
O1 C13 C10 C7 13.6(6) . . . . ?
O1 C13 C14 C15 68.8(6) . . . . ?
O1 C13 C14 C17 -52.0(6) . . . . ?
O4' C13' C10' C7' 9.5(6) . . . . ?
O2' C5' C6' O3' -25.4(5) . . . . ?
O2' C5' C6' C7' -143.7(4) . . . . ?
O2' C5' C6' C12' 92.6(4) . . . . ?
C9' C4' C5' O2' 174.1(4) . . . . ?
C9' C4' C5' C6' -10.2(6) . . . . ?
C9' C8' C1' O1' -0.7(6) . . . . ?
C9' C8' C7' C6' 37.9(5) . . . . ?
C9' C8' C7' C10' 165.9(4) . . . . ?
C5 C6 C7 C8 -50.7(4) . . . . ?
C5 C6 C7 C10 -179.9(3) . . . . ?
C4' C9' C8' C1' 177.9(4) . . . . ?
C4' C9' C8' C7' -8.0(6) . . . . ?
C4' C9' C3' C2' -176.5(4) . . . . ?
C4' C5' C6' O3' 158.6(4) . . . . ?
C4' C5' C6' C7' 40.3(5) . . . . ?
C4' C5' C6' C12' -83.4(5) . . . . ?
C13 C14 C15 C16 173.7(5) . . . . ?
C2' O1' C1' C8' 3.3(6) . . . . ?
C8' C9' C4' C5' -7.2(6) . . . . ?
C8' C9' C3' C2' 4.6(6) . . . . ?
C8' C7' C6' O3' -170.7(3) . . . . ?
C8' C7' C6' C5' -51.8(4) . . . . ?
C8' C7' C6' C12' 68.3(4) . . . . ?
C8' C7' C10' C13' 87.8(4) . . . . ?
C9 C8 C7 C6 35.7(5) . . . . ?
C9 C8 C7 C10 163.9(3) . . . . ?
C9 C8 C1 O4 0.9(6) . . . . ?
C3' C9' C4' C5' 173.9(4) . . . . ?
C3' C9' C8' C1' -3.1(6) . . . . ?
C3' C9' C8' C7' 171.0(4) . . . . ?
C2 O4 C1 C8 4.2(6) . . . . ?
C8 C9 C4 C5 -5.7(6) . . . . ?
C8 C9 C3 C2 5.1(6) . . . . ?
C8 C7 C10 C13 79.6(5) . . . . ?
C4 C5 C6 O2 159.4(3) . . . . ?
C4 C5 C6 C7 41.1(5) . . . . ?
C4 C5 C6 C12 -82.8(4) . . . . ?
C4 C9 C8 C7 -7.1(6) . . . . ?
C4 C9 C8 C1 176.2(4) . . . . ?
C4 C9 C3 C2 -176.5(4) . . . . ?
C14' C13' C10' C7' -172.1(4) . . . . ?
C6 C5 C4 C9 -12.3(6) . . . . ?
C6 C7 C10 C13 -153.4(4) . . . . ?
C13' C14' C15' C16' 63.1(5) . . . . ?
C3 C9 C8 C7 171.3(3) . . . . ?
C3 C9 C8 C1 -5.4(6) . . . . ?
C3 C9 C4 C5 176.0(4) . . . . ?
C7 C8 C1 O4 -175.6(4) . . . . ?
C1' O1' C2' C3' -1.9(6) . . . . ?
C1' O1' C2' C11' 177.7(4) . . . . ?
C1' C8' C7' C6' -148.2(4) . . . . ?
C1' C8' C7' C10' -20.3(6) . . . . ?
C1 O4 C2 C3 -4.5(6) . . . . ?
C1 O4 C2 C11 175.8(3) . . . . ?
C1 C8 C7 C6 -147.7(4) . . . . ?
C1 C8 C7 C10 -19.5(6) . . . . ?
C7' C8' C1' O1' -174.5(4) . . . . ?
C12 C6 C7 C8 70.0(4) . . . . ?
C12 C6 C7 C10 -59.2(5) . . . . ?
C10 C13 C14 C15 -109.0(5) . . . . ?
C10 C13 C14 C17 130.2(5) . . . . ?
C6' C7' C10' C13' -145.8(4) . . . . ?
C10' C7' C6' O3' 60.4(4) . . . . ?
C10' C7' C6' C5' 179.3(3) . . . . ?
C10' C7' C6' C12' -60.5(5) . . . . ?
C11 C2 C3 C9 179.4(4) . . . . ?
C15' C14' C13' O4' 61.5(5) . . . . ?
C15' C14' C13' C10' -117.0(4) . . . . ?
C11' C2' C3' C9' 178.3(4) . . . . ?
C17' C14' C13' O4' -59.8(5) . . . . ?
C17' C14' C13' C10' 121.7(4) . . . . ?
C17' C14' C15' C16' -176.5(4) . . . . ?
C14 C13 C10 C7 -168.6(4) . . . . ?
C17 C14 C15 C16 -66.5(6) . . . . ?

_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 1.845
_oxdiff_exptl_absorpt_empirical_full_min 0.464
