# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_leixx_0507
_database_code_depnum_ccdc_archive 'CCDC 2009364'
loop_
_audit_author_name
_audit_author_address
Acylation
;Lanzhou University
China
;
_audit_update_record             
;
2020-06-12 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_audit_creation_date             2019-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 O7'
_chemical_formula_sum            'C22 H22 O7'
_chemical_formula_weight         398.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.9676(18)
_cell_length_b                   10.3052(9)
_cell_length_c                   24.087(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.230(12)
_cell_angle_gamma                90
_cell_volume                     4067.0(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1356
_cell_measurement_temperature    292.90(10)
_cell_measurement_theta_max      23.5930
_cell_measurement_theta_min      4.0640
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7403
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.518
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.90(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -100.00  -59.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  178.0000 -150.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega  -35.00   80.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000 -120.0000 115

#__ type_ start__ end____ width___ exp.time_
  3 omega   -6.00   63.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000   60.0000 69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0053416000
_diffrn_orient_matrix_UB_12      -0.0638752000
_diffrn_orient_matrix_UB_13      -0.0087298000
_diffrn_orient_matrix_UB_21      -0.0245226000
_diffrn_orient_matrix_UB_22      -0.0245710000
_diffrn_orient_matrix_UB_23      0.0143399000
_diffrn_orient_matrix_UB_31      -0.0352739000
_diffrn_orient_matrix_UB_32      0.0074638000
_diffrn_orient_matrix_UB_33      -0.0275919000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2351
_reflns_number_total             3999
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3999
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0626
_refine_ls_restrained_S_all      1.096
_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)+(0.0286P)²+5.6092P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1511
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C20(H20), C24(H24), C25(H25), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C22(H22A,H22B,H22C), C28(H28A,H28B,H28C), C0AA(H0AA,H0AB,
 H0AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.16128(11) 0.7268(2) 0.09884(8) 0.0464(5) Uani 1 1 d . . . . .
O2 O 0.17279(14) 0.8483(2) -0.00327(10) 0.0569(6) Uani 1 1 d . . . . .
O3 O 0.12495(15) 0.4915(3) 0.29200(9) 0.0628(7) Uani 1 1 d . . . . .
O4 O -0.00635(14) 0.7455(2) -0.04641(9) 0.0613(7) Uani 1 1 d . . . . .
C5 C 0.14656(17) 0.6691(3) 0.14516(12) 0.0386(7) Uani 1 1 d . . . . .
C6 C 0.07011(17) 0.6647(3) 0.14679(12) 0.0400(7) Uani 1 1 d . . . . .
C7 C 0.09401(17) 0.7865(3) 0.04997(12) 0.0390(7) Uani 1 1 d . . . . .
O8 O 0.07727(14) 0.5788(3) -0.00151(11) 0.0646(7) Uani 1 1 d . . . . .
C9 C -0.00210(16) 0.7273(3) 0.09588(12) 0.0417(7) Uani 1 1 d . . . . .
H9 H -0.025328 0.662671 0.063432 0.050 Uiso 1 1 calc R . . . .
O10 O 0.13454(15) 1.0074(2) 0.04259(11) 0.0655(7) Uani 1 1 d . . . . .
C11 C 0.03038(18) 0.8388(3) 0.07046(13) 0.0441(8) Uani 1 1 d . . . . .
H11A H -0.014022 0.878299 0.036286 0.053 Uiso 1 1 calc R . . . .
H11B H 0.054568 0.904477 0.101546 0.053 Uiso 1 1 calc R . . . .
C12 C 0.13514(18) 0.8955(3) 0.02950(12) 0.0434(7) Uani 1 1 d . . . . .
C13 C 0.21481(18) 0.6182(3) 0.19174(12) 0.0442(7) Uani 1 1 d . . . . .
H13 H 0.265356 0.625374 0.189921 0.053 Uiso 1 1 calc R . . . .
C14 C 0.06505(19) 0.6016(3) 0.19594(12) 0.0470(8) Uani 1 1 d . . . . .
H14 H 0.014768 0.595759 0.198273 0.056 Uiso 1 1 calc R . . . .
C15 C 0.20945(19) 0.5566(3) 0.24109(13) 0.0480(8) Uani 1 1 d . . . . .
C16 C 0.1325(2) 0.5477(3) 0.24122(13) 0.0496(8) Uani 1 1 d . . . . .
C17 C -0.06942(18) 0.7689(3) 0.11466(12) 0.0449(8) Uani 1 1 d . . . . .
C18 C 0.05578(19) 0.6878(4) -0.00198(14) 0.0457(8) Uani 1 1 d . . . . .
C19 C 0.2175(2) 0.9406(4) -0.02330(17) 0.0673(10) Uani 1 1 d . . . . .
H19A H 0.243831 0.895882 -0.045229 0.101 Uiso 1 1 calc GR . . . .
H19B H 0.257803 0.983280 0.011465 0.101 Uiso 1 1 calc GR . . . .
H19C H 0.180327 1.003932 -0.049407 0.101 Uiso 1 1 calc GR . . . .
C20 C -0.0557(2) 0.8595(4) 0.16025(15) 0.0666(11) Uani 1 1 d . . . . .
H20 H -0.004451 0.897587 0.179404 0.080 Uiso 1 1 calc R . . . .
O21 O 0.10491(19) 0.2954(3) 0.24845(12) 0.0880(9) Uani 1 1 d . . . . .
C22 C 0.2844(2) 0.5024(4) 0.29232(14) 0.0687(11) Uani 1 1 d . . . . .
H22A H 0.285040 0.409678 0.288679 0.103 Uiso 1 1 calc GR . . . .
H22B H 0.283325 0.524831 0.330668 0.103 Uiso 1 1 calc GR . . . .
H22C H 0.332466 0.538240 0.290164 0.103 Uiso 1 1 calc GR . . . .
C23 C 0.1137(2) 0.3622(4) 0.29117(16) 0.0619(10) Uani 1 1 d . . . . .
C24 C -0.1932(2) 0.8382(4) 0.14993(18) 0.0713(11) Uani 1 1 d . . . . .
H24 H -0.234343 0.860013 0.162193 0.086 Uiso 1 1 calc R . . . .
C25 C -0.1457(2) 0.7159(4) 0.08722(16) 0.0599(9) Uani 1 1 d . . . . .
H25 H -0.156159 0.655171 0.056348 0.072 Uiso 1 1 calc R . . . .
C26 C -0.1177(2) 0.8940(5) 0.17759(16) 0.0760(13) Uani 1 1 d . . . . .
H26 H -0.108021 0.955324 0.208124 0.091 Uiso 1 1 calc R . . . .
C27 C -0.2078(2) 0.7503(4) 0.1043(2) 0.0737(12) Uani 1 1 d . . . . .
H27 H -0.259339 0.713585 0.084699 0.088 Uiso 1 1 calc R . . . .
C28 C -0.0580(2) 0.6657(5) -0.09716(16) 0.0858(14) Uani 1 1 d . . . . .
H28A H -0.093185 0.720364 -0.129568 0.129 Uiso 1 1 calc GR . . . .
H28B H -0.090366 0.609350 -0.084248 0.129 Uiso 1 1 calc GR . . . .
H28C H -0.024537 0.614589 -0.111272 0.129 Uiso 1 1 calc GR . . . .
C0AA C 0.1156(3) 0.3155(5) 0.35035(17) 0.0888(14) Uani 1 1 d . . . . .
H0AA H 0.170620 0.293474 0.377174 0.133 Uiso 1 1 calc GR . . . .
H0AB H 0.081486 0.240235 0.343488 0.133 Uiso 1 1 calc GR . . . .
H0AC H 0.095983 0.382717 0.368487 0.133 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.383(3) . ?
O1 C7 1.434(3) . ?
O2 C12 1.325(4) . ?
O2 C19 1.450(4) . ?
O3 C16 1.409(4) . ?
O3 C23 1.347(5) . ?
O4 C18 1.328(4) . ?
O4 C28 1.449(4) . ?
C5 C6 1.391(4) . ?
C5 C13 1.381(4) . ?
C6 C9 1.515(4) . ?
C6 C14 1.386(4) . ?
C7 C11 1.518(4) . ?
C7 C12 1.533(4) . ?
C7 C18 1.538(4) . ?
O8 C18 1.187(4) . ?
C9 H9 0.9800 . ?
C9 C11 1.526(4) . ?
C9 C17 1.517(4) . ?
O10 C12 1.196(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 H13 0.9300 . ?
C13 C15 1.385(4) . ?
C14 H14 0.9300 . ?
C14 C16 1.372(4) . ?
C15 C16 1.387(4) . ?
C15 C22 1.512(4) . ?
C17 C20 1.384(4) . ?
C17 C25 1.368(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C26 1.389(5) . ?
O21 C23 1.194(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C0AA 1.491(5) . ?
C24 H24 0.9300 . ?
C24 C26 1.368(5) . ?
C24 C27 1.364(5) . ?
C25 H25 0.9300 . ?
C25 C27 1.383(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C0AA H0AA 0.9600 . ?
C0AA H0AB 0.9600 . ?
C0AA H0AC 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
C5 O1 C7 118.1(2) . . ?
C12 O2 C19 116.4(3) . . ?
C23 O3 C16 117.4(3) . . ?
C18 O4 C28 117.5(3) . . ?
O1 C5 C6 123.7(2) . . ?
C13 C5 O1 114.8(3) . . ?
C13 C5 C6 121.5(3) . . ?
C5 C6 C9 119.4(3) . . ?
C14 C6 C5 116.8(3) . . ?
C14 C6 C9 123.8(3) . . ?
O1 C7 C11 112.3(2) . . ?
O1 C7 C12 102.9(2) . . ?
O1 C7 C18 109.2(2) . . ?
C11 C7 C12 111.8(3) . . ?
C11 C7 C18 110.8(2) . . ?
C12 C7 C18 109.6(2) . . ?
C6 C9 H9 107.4 . . ?
C6 C9 C11 107.7(2) . . ?
C6 C9 C17 113.7(2) . . ?
C11 C9 H9 107.4 . . ?
C17 C9 H9 107.4 . . ?
C17 C9 C11 112.9(3) . . ?
C7 C11 C9 109.1(2) . . ?
C7 C11 H11A 109.9 . . ?
C7 C11 H11B 109.9 . . ?
C9 C11 H11A 109.9 . . ?
C9 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
O2 C12 C7 110.7(3) . . ?
O10 C12 O2 125.0(3) . . ?
O10 C12 C7 124.3(3) . . ?
C5 C13 H13 119.3 . . ?
C5 C13 C15 121.3(3) . . ?
C15 C13 H13 119.3 . . ?
C6 C14 H14 119.2 . . ?
C16 C14 C6 121.6(3) . . ?
C16 C14 H14 119.2 . . ?
C13 C15 C16 116.9(3) . . ?
C13 C15 C22 121.2(3) . . ?
C16 C15 C22 121.9(3) . . ?
C14 C16 O3 119.2(3) . . ?
C14 C16 C15 121.8(3) . . ?
C15 C16 O3 118.7(3) . . ?
C20 C17 C9 121.5(3) . . ?
C25 C17 C9 120.4(3) . . ?
C25 C17 C20 118.0(3) . . ?
O4 C18 C7 107.9(3) . . ?
O8 C18 O4 126.4(3) . . ?
O8 C18 C7 125.7(3) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20 119.8 . . ?
C17 C20 C26 120.5(3) . . ?
C26 C20 H20 119.8 . . ?
C15 C22 H22A 109.5 . . ?
C15 C22 H22B 109.5 . . ?
C15 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 C0AA 111.1(4) . . ?
O21 C23 O3 123.3(3) . . ?
O21 C23 C0AA 125.5(4) . . ?
C26 C24 H24 120.1 . . ?
C27 C24 H24 120.1 . . ?
C27 C24 C26 119.8(3) . . ?
C17 C25 H25 119.2 . . ?
C17 C25 C27 121.6(3) . . ?
C27 C25 H25 119.2 . . ?
C20 C26 H26 119.9 . . ?
C24 C26 C20 120.2(4) . . ?
C24 C26 H26 119.9 . . ?
C24 C27 C25 119.8(4) . . ?
C24 C27 H27 120.1 . . ?
C25 C27 H27 120.1 . . ?
O4 C28 H28A 109.5 . . ?
O4 C28 H28B 109.5 . . ?
O4 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C23 C0AA H0AA 109.5 . . ?
C23 C0AA H0AB 109.5 . . ?
C23 C0AA H0AC 109.5 . . ?
H0AA C0AA H0AB 109.5 . . ?
H0AA C0AA H0AC 109.5 . . ?
H0AB C0AA H0AC 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 C5 C6 C9 -0.7(4) . . . . ?
O1 C5 C6 C14 179.1(3) . . . . ?
O1 C5 C13 C15 -179.6(3) . . . . ?
O1 C7 C11 C9 -59.5(3) . . . . ?
O1 C7 C12 O2 76.6(3) . . . . ?
O1 C7 C12 O10 -102.0(3) . . . . ?
O1 C7 C18 O4 179.8(2) . . . . ?
O1 C7 C18 O8 1.3(4) . . . . ?
C5 O1 C7 C11 29.9(4) . . . . ?
C5 O1 C7 C12 150.3(2) . . . . ?
C5 O1 C7 C18 -93.3(3) . . . . ?
C5 C6 C9 C11 -28.5(4) . . . . ?
C5 C6 C9 C17 -154.4(3) . . . . ?
C5 C6 C14 C16 0.9(5) . . . . ?
C5 C13 C15 C16 0.5(5) . . . . ?
C5 C13 C15 C22 -179.3(3) . . . . ?
C6 C5 C13 C15 2.2(5) . . . . ?
C6 C9 C11 C7 56.6(3) . . . . ?
C6 C9 C17 C20 60.9(4) . . . . ?
C6 C9 C17 C25 -118.2(3) . . . . ?
C6 C14 C16 O3 176.2(3) . . . . ?
C6 C14 C16 C15 1.9(5) . . . . ?
C7 O1 C5 C6 0.5(4) . . . . ?
C7 O1 C5 C13 -177.6(3) . . . . ?
C9 C6 C14 C16 -179.3(3) . . . . ?
C9 C17 C20 C26 -178.6(3) . . . . ?
C9 C17 C25 C27 178.7(3) . . . . ?
C11 C7 C12 O2 -162.8(2) . . . . ?
C11 C7 C12 O10 18.7(4) . . . . ?
C11 C7 C18 O4 55.7(3) . . . . ?
C11 C7 C18 O8 -122.8(3) . . . . ?
C11 C9 C17 C20 -62.2(4) . . . . ?
C11 C9 C17 C25 118.8(3) . . . . ?
C12 C7 C11 C9 -174.6(2) . . . . ?
C12 C7 C18 O4 -68.2(3) . . . . ?
C12 C7 C18 O8 113.3(4) . . . . ?
C13 C5 C6 C9 177.3(3) . . . . ?
C13 C5 C6 C14 -2.9(4) . . . . ?
C13 C15 C16 O3 -176.9(3) . . . . ?
C13 C15 C16 C14 -2.6(5) . . . . ?
C14 C6 C9 C11 151.7(3) . . . . ?
C14 C6 C9 C17 25.8(4) . . . . ?
C16 O3 C23 O21 -4.7(5) . . . . ?
C16 O3 C23 C0AA 174.0(3) . . . . ?
C17 C9 C11 C7 -177.1(2) . . . . ?
C17 C20 C26 C24 0.3(6) . . . . ?
C17 C25 C27 C24 -0.7(6) . . . . ?
C18 C7 C11 C9 62.8(3) . . . . ?
C18 C7 C12 O2 -39.5(3) . . . . ?
C18 C7 C12 O10 142.0(3) . . . . ?
C19 O2 C12 C7 -177.3(2) . . . . ?
C19 O2 C12 O10 1.2(4) . . . . ?
C20 C17 C25 C27 -0.4(5) . . . . ?
C22 C15 C16 O3 2.9(5) . . . . ?
C22 C15 C16 C14 177.3(3) . . . . ?
C23 O3 C16 C14 96.4(4) . . . . ?
C23 O3 C16 C15 -89.2(4) . . . . ?
C25 C17 C20 C26 0.5(5) . . . . ?
C26 C24 C27 C25 1.5(6) . . . . ?
C27 C24 C26 C20 -1.4(6) . . . . ?
C28 O4 C18 C7 -172.5(3) . . . . ?
C28 O4 C18 O8 5.9(5) . . . . ?

_olex2_date_sample_data_collection 2019-05-07
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_leixx_0526
_database_code_depnum_ccdc_archive 'CCDC 2009365'
loop_
_audit_author_name
_audit_author_address
Oxidation
;Lanzhou University
China
;
_audit_update_record             
;
2020-06-12 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_audit_creation_date             2020-06-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 O6'
_chemical_formula_sum            'C20 H20 O6'
_chemical_formula_weight         356.36
_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.4049(3)
_cell_length_b                   8.66607(17)
_cell_length_c                   26.3242(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.968(2)
_cell_angle_gamma                90
_cell_volume                     3674.04(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3155
_cell_measurement_temperature    293.29(10)
_cell_measurement_theta_max      69.5170
_cell_measurement_theta_min      6.2770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6990
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.714
_diffrn_reflns_theta_min         3.420
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.29(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_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     31.00  59.00   1.00    1.00    --   54.00 -57.00   0.00   28
  2  ω     34.00  60.00   1.00    1.00    --   54.00-125.00 -30.00   26
  3  ω     80.00 133.00   1.00    1.00    --  108.00 -91.00 -30.00   53
  4  ω     55.00 117.00   1.00    1.00    --  108.00 -50.00-180.00   62
  5  ω     35.00  88.00   1.00    1.00    --  108.00 -25.00-120.00   53
  6  ω     36.00  65.00   1.00    1.00    --  108.00 -91.00 -30.00   29
  7  ω      4.00  93.00   1.00    1.00    --   54.00 -99.00-120.00   89
  8  ω      5.00  67.00   1.00    1.00    --    0.00  38.00 -30.00   62
  9  ω     29.00 125.00   1.00    1.00    --   54.00  38.00  30.00   96
 10  ω     95.00 122.00   1.00    1.00    --   54.00  57.00 120.00   27
 11  ω     80.00 119.00   1.00    1.00    --  108.00  25.00 150.00   39
 12  ω    104.00 178.00   1.00    1.00    --  108.00  38.00  60.00   74
 13  ω    104.00 178.00   1.00    1.00    --  108.00 111.00 -60.00   74
 14  ω    145.00 176.00   1.00    1.00    --  108.00 111.00-120.00   31
 15  ω     88.00 177.00   1.00    1.00    --  108.00  50.00   0.00   89
 16  ω     32.00  61.00   1.00    1.00    --    0.00  57.00-150.00   29
 17  ω    -19.00  21.00   1.00    1.00    --    0.00  57.00-150.00   40
 18  ω     33.00  87.00   1.00    1.00    --   54.00  57.00 120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0904016000
_diffrn_orient_matrix_UB_12      -0.0582631000
_diffrn_orient_matrix_UB_13      0.0103849000
_diffrn_orient_matrix_UB_21      0.0194590000
_diffrn_orient_matrix_UB_22      0.1068384000
_diffrn_orient_matrix_UB_23      -0.0429205000
_diffrn_orient_matrix_UB_31      0.0246170000
_diffrn_orient_matrix_UB_32      0.1294783000
_diffrn_orient_matrix_UB_33      0.0400629000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2932
_reflns_number_total             3402
_reflns_odcompleteness_completeness 99.74
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3402
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²+2.1222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1393
_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:
 C10(H10), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C17(H17), C19(H19), C18(H18), C3(H3), C16(H16), C20(H20)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.00155(8) 0.23283(15) 0.12202(5) 0.0576(4) Uani 1 1 d . . . . .
O5 O -0.15205(10) 0.2539(3) -0.00936(8) 0.1126(8) Uani 1 1 d . . . . .
O3 O 0.04386(9) 0.47329(17) 0.11632(7) 0.0818(5) Uani 1 1 d . . . . .
O2 O -0.40681(10) 0.19294(18) 0.17061(7) 0.0742(4) Uani 1 1 d . . . . .
O6 O -0.01679(8) 0.2724(2) 0.00662(5) 0.0680(4) Uani 1 1 d . . . . .
O1 O -0.17099(10) 0.6020(2) 0.23175(6) 0.0807(5) Uani 1 1 d . . . . .
C10 C -0.08686(9) 0.39494(19) 0.06558(6) 0.0423(4) Uani 1 1 d . . . . .
H10 H -0.089923 0.503285 0.054719 0.051 Uiso 1 1 calc R U . . .
C4 C -0.35479(13) 0.3865(3) 0.23114(7) 0.0610(5) Uani 1 1 d . . . . .
C15 C -0.19064(10) 0.64045(18) 0.11198(6) 0.0401(4) Uani 1 1 d . . . . .
C9 C -0.16203(10) 0.36333(19) 0.09086(7) 0.0433(4) Uani 1 1 d . . . . .
H9A H -0.212181 0.367290 0.064548 0.052 Uiso 1 1 calc R U . . .
H9B H -0.157408 0.260124 0.105384 0.052 Uiso 1 1 calc R U . . .
C2 C -0.22812(12) 0.5145(2) 0.21590(7) 0.0543(5) Uani 1 1 d . . . . .
C8 C -0.16940(10) 0.47911(18) 0.13354(6) 0.0403(4) Uani 1 1 d . . . . .
H8 H -0.115201 0.484770 0.156787 0.048 Uiso 1 1 calc R U . . .
C12 C 0.07546(13) 0.1985(3) 0.16022(9) 0.0715(6) Uani 1 1 d . . . . .
H12A H 0.123905 0.222432 0.146224 0.107 Uiso 1 1 calc R U . . .
H12B H 0.075919 0.090967 0.169022 0.107 Uiso 1 1 calc R U . . .
H12C H 0.075464 0.259412 0.190680 0.107 Uiso 1 1 calc R U . . .
C6 C -0.29245(11) 0.3274(2) 0.15183(7) 0.0479(4) Uani 1 1 d . . . . .
H6 H -0.294659 0.273597 0.121027 0.057 Uiso 1 1 calc R U . . .
C13 C -0.09036(11) 0.2977(2) 0.01741(7) 0.0490(4) Uani 1 1 d . . . . .
C17 C -0.15541(14) 0.9076(2) 0.10345(8) 0.0628(5) Uani 1 1 d . . . . .
H17 H -0.117578 0.988004 0.111467 0.075 Uiso 1 1 calc R U . . .
C19 C -0.28568(14) 0.8153(3) 0.05978(9) 0.0684(6) Uani 1 1 d . . . . .
H19 H -0.336738 0.833127 0.038299 0.082 Uiso 1 1 calc R U . . .
C18 C -0.23040(15) 0.9340(2) 0.07160(8) 0.0652(6) Uani 1 1 d . . . . .
H18 H -0.243632 1.031960 0.058099 0.078 Uiso 1 1 calc R U . . .
C3 C -0.29381(14) 0.4874(3) 0.24553(7) 0.0650(6) Uani 1 1 d . . . . .
H3 H -0.292776 0.543284 0.275801 0.078 Uiso 1 1 calc R U . . .
C7 C -0.42397(17) 0.3591(4) 0.26003(10) 0.0929(9) Uani 1 1 d . . . . .
H7A H -0.476036 0.384792 0.238245 0.139 Uiso 1 1 calc R U . . .
H7B H -0.415782 0.422603 0.290474 0.139 Uiso 1 1 calc R U . . .
H7C H -0.424347 0.252513 0.269871 0.139 Uiso 1 1 calc R U . . .
C1 C -0.23266(10) 0.43156(19) 0.16556(6) 0.0418(4) Uani 1 1 d . . . . .
C16 C -0.13553(12) 0.7619(2) 0.12381(7) 0.0522(4) Uani 1 1 d . . . . .
H16 H -0.084641 0.745591 0.145653 0.063 Uiso 1 1 calc R U . . .
C14 C -0.01407(16) 0.1858(3) -0.04003(8) 0.0786(7) Uani 1 1 d . . . . .
H14A H -0.037610 0.246641 -0.069689 0.118 Uiso 1 1 calc R U . . .
H14B H -0.045334 0.092229 -0.039943 0.118 Uiso 1 1 calc R U . . .
H14C H 0.042522 0.161244 -0.041407 0.118 Uiso 1 1 calc R U . . .
C11 C -0.00580(10) 0.37404(19) 0.10351(7) 0.0445(4) Uani 1 1 d . . . . .
C5 C -0.35526(11) 0.2941(2) 0.18360(7) 0.0537(5) Uani 1 1 d . . . . .
C20 C -0.26627(11) 0.6683(2) 0.07960(8) 0.0548(5) Uani 1 1 d . . . . .
H20 H -0.304195 0.588293 0.071094 0.066 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
O4 C12 1.451(2) . ?
O4 C11 1.314(2) . ?
O5 C13 1.181(2) . ?
O3 C11 1.189(2) . ?
O2 C5 1.221(2) . ?
O6 C13 1.310(2) . ?
O6 C14 1.447(3) . ?
O1 C2 1.216(2) . ?
C10 H10 0.9800 . ?
C10 C9 1.533(2) . ?
C10 C13 1.514(2) . ?
C10 C11 1.514(2) . ?
C4 C3 1.328(3) . ?
C4 C7 1.500(3) . ?
C4 C5 1.484(3) . ?
C15 C8 1.524(2) . ?
C15 C16 1.384(2) . ?
C15 C20 1.386(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.528(2) . ?
C2 C3 1.465(3) . ?
C2 C1 1.497(3) . ?
C8 H8 0.9800 . ?
C8 C1 1.513(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C6 H6 0.9300 . ?
C6 C1 1.331(2) . ?
C6 C5 1.474(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.370(3) . ?
C17 C16 1.386(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.367(3) . ?
C19 C20 1.391(3) . ?
C18 H18 0.9300 . ?
C3 H3 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C16 H16 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O4 C12 116.96(16) . . ?
C13 O6 C14 116.70(16) . . ?
C9 C10 H10 107.3 . . ?
C13 C10 H10 107.3 . . ?
C13 C10 C9 111.01(13) . . ?
C11 C10 H10 107.3 . . ?
C11 C10 C9 111.74(14) . . ?
C11 C10 C13 111.98(13) . . ?
C3 C4 C7 124.1(2) . . ?
C3 C4 C5 118.58(18) . . ?
C5 C4 C7 117.3(2) . . ?
C16 C15 C8 121.37(14) . . ?
C16 C15 C20 118.43(16) . . ?
C20 C15 C8 120.21(15) . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C8 C9 C10 112.61(13) . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
O1 C2 C3 120.96(18) . . ?
O1 C2 C1 120.57(18) . . ?
C3 C2 C1 118.47(17) . . ?
C15 C8 C9 111.89(13) . . ?
C15 C8 H8 107.6 . . ?
C9 C8 H8 107.6 . . ?
C1 C8 C15 108.95(13) . . ?
C1 C8 C9 112.91(13) . . ?
C1 C8 H8 107.6 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C6 H6 118.8 . . ?
C1 C6 C5 122.48(17) . . ?
C5 C6 H6 118.8 . . ?
O5 C13 O6 122.48(18) . . ?
O5 C13 C10 124.79(17) . . ?
O6 C13 C10 112.65(15) . . ?
C18 C17 H17 119.8 . . ?
C18 C17 C16 120.42(19) . . ?
C16 C17 H17 119.8 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.61(19) . . ?
C20 C19 H19 119.7 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.57(18) . . ?
C19 C18 H18 120.2 . . ?
C4 C3 C2 122.98(19) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C1 C8 116.01(14) . . ?
C6 C1 C2 118.42(16) . . ?
C6 C1 C8 125.53(15) . . ?
C15 C16 C17 120.68(18) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
O6 C14 H14A 109.5 . . ?
O6 C14 H14B 109.5 . . ?
O6 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C11 C10 111.28(14) . . ?
O3 C11 O4 123.99(16) . . ?
O3 C11 C10 124.69(16) . . ?
O2 C5 C4 121.06(18) . . ?
O2 C5 C6 120.21(19) . . ?
C6 C5 C4 118.73(17) . . ?
C15 C20 C19 120.29(18) . . ?
C15 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?

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 C4 -176.2(2) . . . . ?
O1 C2 C1 C8 -7.6(3) . . . . ?
O1 C2 C1 C6 174.52(19) . . . . ?
C10 C9 C8 C15 67.84(17) . . . . ?
C10 C9 C8 C1 -168.80(13) . . . . ?
C15 C8 C1 C2 -70.48(17) . . . . ?
C15 C8 C1 C6 107.20(18) . . . . ?
C9 C10 C13 O5 28.8(3) . . . . ?
C9 C10 C13 O6 -154.31(15) . . . . ?
C9 C10 C11 O4 59.67(19) . . . . ?
C9 C10 C11 O3 -118.1(2) . . . . ?
C9 C8 C1 C2 164.54(14) . . . . ?
C9 C8 C1 C6 -17.8(2) . . . . ?
C8 C15 C16 C17 179.31(17) . . . . ?
C8 C15 C20 C19 -179.84(18) . . . . ?
C12 O4 C11 O3 -0.3(3) . . . . ?
C12 O4 C11 C10 -178.05(16) . . . . ?
C13 C10 C9 C8 -169.50(13) . . . . ?
C13 C10 C11 O4 -65.58(19) . . . . ?
C13 C10 C11 O3 116.6(2) . . . . ?
C18 C17 C16 C15 0.6(3) . . . . ?
C18 C19 C20 C15 0.5(3) . . . . ?
C3 C4 C5 O2 175.2(2) . . . . ?
C3 C4 C5 C6 -5.3(3) . . . . ?
C3 C2 C1 C8 172.57(16) . . . . ?
C3 C2 C1 C6 -5.3(3) . . . . ?
C7 C4 C3 C2 -178.5(2) . . . . ?
C7 C4 C5 O2 -4.7(3) . . . . ?
C7 C4 C5 C6 174.80(19) . . . . ?
C1 C2 C3 C4 3.6(3) . . . . ?
C1 C6 C5 O2 -176.85(18) . . . . ?
C1 C6 C5 C4 3.6(3) . . . . ?
C16 C15 C8 C9 -114.70(17) . . . . ?
C16 C15 C8 C1 119.73(17) . . . . ?
C16 C15 C20 C19 -0.1(3) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C14 O6 C13 O5 -0.5(3) . . . . ?
C14 O6 C13 C10 -177.48(18) . . . . ?
C11 C10 C9 C8 64.71(18) . . . . ?
C11 C10 C13 O5 154.4(2) . . . . ?
C11 C10 C13 O6 -28.6(2) . . . . ?
C5 C4 C3 C2 1.6(3) . . . . ?
C5 C6 C1 C2 1.7(3) . . . . ?
C5 C6 C1 C8 -175.98(15) . . . . ?
C20 C15 C8 C9 65.0(2) . . . . ?
C20 C15 C8 C1 -60.5(2) . . . . ?
C20 C15 C16 C17 -0.4(3) . . . . ?
C20 C19 C18 C17 -0.3(3) . . . . ?

_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 1.130
_oxdiff_exptl_absorpt_empirical_full_min 0.804
####################################################################### 
# 
# 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_wangyang_0512_auto
_database_code_depnum_ccdc_archive 'CCDC 2172704'
loop_
_audit_author_name
_audit_author_address
'Jia-Lu '
;Lanzhou University 
China
;
_audit_update_record             
;
2022-05-14 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_audit_creation_date             2022-05-13
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 O6'
_chemical_formula_sum            'C21 H20 O6'
_chemical_formula_weight         368.37
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.0449(2)
_cell_length_b                   7.77050(10)
_cell_length_c                   27.9991(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.6420(10)
_cell_angle_gamma                90
_cell_volume                     3666.30(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10448
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.9520
_cell_measurement_theta_min      1.6210
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.888
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
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    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11635
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.429
_diffrn_reflns_theta_min         5.723
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00 -30.00   50
  2  ω     42.00 100.00   0.50    0.05    --  107.75 -77.00-180.00  116
  3  ω     35.00  63.00   0.50    0.05    --  107.75 -57.00-150.00   56
  4  ω     35.00  61.00   0.50    0.05    --  107.75 -57.00-120.00   52
  5  ω    -26.00  35.00   0.50    0.05    --   47.45 -37.00  30.00  122
  6  ω     95.00 156.00   0.50    0.05    --  107.75  57.00 -90.00  122
  7  ω     85.00 167.00   0.50    0.05    --  107.75  97.00 -68.00  164
  8  ω    -40.00 -14.00   0.50    0.05    --  -47.45  97.00 -68.00   52
  9  ω    -96.00 -58.00   0.50    0.05    -- -100.00  97.00 -68.00   76
 10  ω    -93.00 -35.00   0.50    0.05    -- -100.00 125.00  60.00  116
 11  ω    -65.00 -29.00   0.50    0.05    -- -100.00  57.00 150.00   72
 12  ω    -68.00 -28.00   0.50    0.05    -- -100.00  57.00 120.00   80
 13  ω    -62.00 -35.00   0.50    0.05    -- -100.00  57.00  90.00   54
 14  ω    -68.00 -27.00   0.50    0.05    -- -100.00  57.00  60.00   82
 15  ω    -55.00 -28.00   0.50    0.05    -- -100.00  57.00 -90.00   54
 16  ω   -120.00 -33.00   0.50    0.05    --  -47.45 -77.00  30.00  174
 17  ω   -168.00 -97.00   0.50    0.05    -- -100.00 -97.00-176.00  142
 18  ω    -14.00  80.00   0.50    0.05    --   47.45 -97.00-176.00  188
 19  ω     60.00 106.00   0.50    0.05    --  107.75 -97.00-176.00   92
 20  ω     42.00  84.00   0.50    0.05    --  107.75 -99.00  60.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0725825000
_diffrn_orient_matrix_UB_12      0.0992706000
_diffrn_orient_matrix_UB_13      -0.0123373000
_diffrn_orient_matrix_UB_21      -0.0528227000
_diffrn_orient_matrix_UB_22      0.1580926000
_diffrn_orient_matrix_UB_23      -0.0144741000
_diffrn_orient_matrix_UB_31      0.0171215000
_diffrn_orient_matrix_UB_32      0.0670451000
_diffrn_orient_matrix_UB_33      0.0522977000
_diffrn_radiation_monochromator  mirror
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3549
_reflns_number_total             3641
_reflns_odcompleteness_completeness 98.50
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3641
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+3.3998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.0996
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C7(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H15), C21(H31), C22(H33), C34(H40), C38(H47), C32(H39)
2.c Idealised Me refined as rotating group:
 C10(H18,H19,H20), C17(H28,H29,H30), C35(H41,H42,H43), C36(H44,H45,H46)
2.d Idealised tetrahedral OH refined as rotating group:
 O27(H37)
;
_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 0.60547(5) 0.19273(11) 0.57134(3) 0.0229(2) Uani 1 1 d . . . . .
O002 O 0.60979(5) 0.61803(12) 0.62527(3) 0.0258(2) Uani 1 1 d . . . . .
O003 O 0.86979(5) -0.06833(14) 0.50913(3) 0.0335(2) Uani 1 1 d . . . . .
H003 H 0.909460 -0.055014 0.530544 0.050 Uiso 1 1 calc GR . . . .
O004 O 0.49764(5) 0.50372(14) 0.58623(4) 0.0346(2) Uani 1 1 d . . . . .
O005 O 0.46684(7) 0.35107(14) 0.67942(4) 0.0430(3) Uani 1 1 d . . . . .
O006 O 0.49746(7) 0.08972(14) 0.65415(5) 0.0517(3) Uani 1 1 d . . . . .
C007 C 0.71364(7) 0.18749(15) 0.62963(4) 0.0213(3) Uani 1 1 d . . . . .
C008 C 0.76638(7) 0.21087(16) 0.67591(4) 0.0221(3) Uani 1 1 d . . . . .
C009 C 0.73604(7) 0.11790(16) 0.58564(4) 0.0214(3) Uani 1 1 d . . . . .
C00A C 0.58298(7) 0.33375(16) 0.64546(4) 0.0231(3) Uani 1 1 d . . . . .
H00A H 0.615632 0.373559 0.676153 0.028 Uiso 1 1 calc R . . . .
C00B C 0.66818(7) 0.12343(16) 0.55143(4) 0.0217(3) Uani 1 1 d . . . . .
C00C C 0.63595(7) 0.22973(16) 0.61864(4) 0.0217(3) Uani 1 1 d . . . . .
C00D C 0.55667(7) 0.49406(16) 0.61549(4) 0.0227(3) Uani 1 1 d . . . . .
C00E C 0.80604(7) 0.05155(17) 0.57249(4) 0.0236(3) Uani 1 1 d . . . . .
H00E H 0.853499 0.044794 0.595053 0.028 Uiso 1 1 calc R . . . .
C00F C 0.73338(7) -0.00008(16) 0.49110(4) 0.0239(3) Uani 1 1 d . . . . .
C00G C 0.80341(7) -0.00378(16) 0.52535(5) 0.0244(3) Uani 1 1 d . . . . .
C00H C 0.84160(8) 0.28301(18) 0.67653(5) 0.0273(3) Uani 1 1 d . . . . .
H00H H 0.857874 0.319016 0.647106 0.033 Uiso 1 1 calc R . . . .
C00I C 0.66330(7) 0.06557(16) 0.50418(4) 0.0234(3) Uani 1 1 d . . . . .
C00J C 0.74412(8) 0.15763(17) 0.71966(5) 0.0256(3) Uani 1 1 d . . . . .
H00J H 0.693378 0.107373 0.719905 0.031 Uiso 1 1 calc R . . . .
C00K C 0.51100(8) 0.23970(18) 0.65905(5) 0.0292(3) Uani 1 1 d . . . . .
C00L C 0.58662(8) 0.0773(2) 0.46988(5) 0.0304(3) Uani 1 1 d . . . . .
H00B H 0.567765 -0.038780 0.460538 0.046 Uiso 1 1 calc GR . . . .
H00C H 0.595282 0.141642 0.441023 0.046 Uiso 1 1 calc GR . . . .
H00D H 0.546852 0.136756 0.485740 0.046 Uiso 1 1 calc GR . . . .
C00M C 0.73628(8) -0.06791(19) 0.44110(5) 0.0301(3) Uani 1 1 d . . . . .
H00F H 0.770402 0.006321 0.424753 0.045 Uiso 1 1 calc GR . . . .
H00G H 0.682602 -0.069126 0.422727 0.045 Uiso 1 1 calc GR . . . .
H00I H 0.757731 -0.185136 0.443228 0.045 Uiso 1 1 calc GR . . . .
C00N C 0.59464(9) 0.77527(18) 0.59719(5) 0.0335(3) Uani 1 1 d . . . . .
H00K H 0.590369 0.748247 0.562703 0.050 Uiso 1 1 calc GR . . . .
H00L H 0.638407 0.856294 0.606236 0.050 Uiso 1 1 calc GR . . . .
H00M H 0.544927 0.827181 0.603702 0.050 Uiso 1 1 calc GR . . . .
C00O C 0.79553(8) 0.17755(19) 0.76278(5) 0.0308(3) Uani 1 1 d . . . . .
H00O H 0.779713 0.141629 0.792341 0.037 Uiso 1 1 calc R . . . .
C00P C 0.86995(8) 0.2499(2) 0.76270(5) 0.0337(3) Uani 1 1 d . . . . .
H00P H 0.905184 0.263120 0.792150 0.040 Uiso 1 1 calc R . . . .
C00Q C 0.89274(8) 0.3027(2) 0.71957(5) 0.0329(3) Uani 1 1 d . . . . .
H00Q H 0.943617 0.352499 0.719499 0.039 Uiso 1 1 calc R . . . .
C00R C 0.39513(11) 0.2846(2) 0.69432(8) 0.0534(5) Uani 1 1 d . . . . .
H00N H 0.361079 0.235471 0.666332 0.080 Uiso 1 1 calc GR . . . .
H00R H 0.366877 0.378233 0.707911 0.080 Uiso 1 1 calc GR . . . .
H00S H 0.408785 0.195196 0.718837 0.080 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00B 1.3867(14) . ?
O001 C00C 1.3783(14) . ?
O002 C00D 1.3222(15) . ?
O002 C00N 1.4549(16) . ?
O003 C00G 1.3757(15) . ?
O004 C00D 1.2006(15) . ?
O005 C00K 1.3304(17) . ?
O005 C00R 1.4449(18) . ?
O006 C00K 1.1920(18) . ?
C007 C008 1.4730(17) . ?
C007 C009 1.4479(17) . ?
C007 C00C 1.3540(17) . ?
C008 C00H 1.3971(18) . ?
C008 C00J 1.3983(17) . ?
C009 C00B 1.3872(17) . ?
C009 C00E 1.3990(17) . ?
C00A C00C 1.4954(17) . ?
C00A C00D 1.5311(17) . ?
C00A C00K 1.5247(17) . ?
C00B C00I 1.3879(17) . ?
C00E C00G 1.3825(18) . ?
C00F C00G 1.4146(18) . ?
C00F C00I 1.3973(18) . ?
C00F C00M 1.5037(17) . ?
C00H C00Q 1.3855(19) . ?
C00I C00L 1.5038(17) . ?
C00J C00O 1.3900(19) . ?
C00O C00P 1.388(2) . ?
C00P C00Q 1.385(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00C O001 C00B 105.38(9) . . ?
C00D O002 C00N 116.07(10) . . ?
C00K O005 C00R 116.69(12) . . ?
C009 C007 C008 126.17(11) . . ?
C00C C007 C008 128.08(11) . . ?
C00C C007 C009 105.73(10) . . ?
C00H C008 C007 119.87(11) . . ?
C00H C008 C00J 118.49(11) . . ?
C00J C008 C007 121.61(11) . . ?
C00B C009 C007 106.07(10) . . ?
C00B C009 C00E 119.03(11) . . ?
C00E C009 C007 134.91(11) . . ?
C00C C00A C00D 108.28(10) . . ?
C00C C00A C00K 115.82(11) . . ?
C00K C00A C00D 110.26(10) . . ?
O001 C00B C009 110.34(10) . . ?
O001 C00B C00I 124.73(11) . . ?
C009 C00B C00I 124.93(11) . . ?
O001 C00C C00A 115.24(10) . . ?
C007 C00C O001 112.49(11) . . ?
C007 C00C C00A 131.34(11) . . ?
O002 C00D C00A 110.13(10) . . ?
O004 C00D O002 124.99(12) . . ?
O004 C00D C00A 124.84(12) . . ?
C00G C00E C009 117.34(11) . . ?
C00G C00F C00M 118.79(11) . . ?
C00I C00F C00G 119.82(11) . . ?
C00I C00F C00M 121.40(11) . . ?
O003 C00G C00E 121.21(11) . . ?
O003 C00G C00F 115.83(11) . . ?
C00E C00G C00F 122.95(11) . . ?
C00Q C00H C008 120.75(12) . . ?
C00B C00I C00F 115.91(11) . . ?
C00B C00I C00L 120.72(11) . . ?
C00F C00I C00L 123.37(11) . . ?
C00O C00J C008 120.63(12) . . ?
O005 C00K C00A 108.88(11) . . ?
O006 C00K O005 124.97(13) . . ?
O006 C00K C00A 126.09(12) . . ?
C00P C00O C00J 120.04(12) . . ?
C00Q C00P C00O 119.85(12) . . ?
C00P C00Q C00H 120.23(13) . . ?

_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 1.810
_oxdiff_exptl_absorpt_empirical_full_min 0.702
