# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
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data_11
_audit_block_doi                 10.5517/ccdc.csd.cc2fgnp8
_database_code_depnum_ccdc_archive 'CCDC 2248420'
loop_
_audit_author_name
_audit_author_address
'chengyu yu' 'shihezhi University'
_audit_update_record             
;
2023-03-14 deposited with the CCDC.	2023-10-06 downloaded from the CCDC.
;
_audit_creation_date             2023-02-28
_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         'C17 H21 N O5'
_chemical_formula_sum            'C17 H21 N O5'
_chemical_formula_weight         319.35
_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'
N N 0.0311 0.0180 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2667(3)
_cell_length_b                   9.3632(3)
_cell_length_c                   10.5150(3)
_cell_angle_alpha                99.5740(10)
_cell_angle_beta                 114.0520(10)
_cell_angle_gamma                97.0690(10)
_cell_volume                     802.86(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.47
_cell_measurement_theta_min      4.74
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.889
_exptl_absorpt_coefficient_mu    0.806
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1105 before and 0.0840 after correction. The Ratio of minimum to maximum transmission is 0.9030. The λ/2 correction factor is Not present.'
_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    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19171
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.044
_diffrn_reflns_theta_min         4.742
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2754
_reflns_number_total             3124
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3124
_refine_ls_number_restraints     128
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      1.060
_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)+(0.0727P)²+0.6399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.1608
_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. Restrained distances
 O2A-C2 \\sim O2-C2
 with sigma of 0.02
 O2A-C1A \\sim O2-C1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C1 \\sim C1A \\sim C2 \\sim O1 \\sim O1A \\sim O2 \\sim O2A: within 3.8A with
sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(O1A)=Sof(O2A)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(O1)=Sof(O2)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C11(H11)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
5.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C1A(H1AA,H1AB,H1AC), C3(H3A,H3B,H3C), C8(H8A,H8B,H8C)
5.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1315(15) 1.1271(12) 0.9199(14) 0.049(2) Uani 0.783(13) 1 d D U P A 1
H1A H 0.079462 1.156699 0.829426 0.074 Uiso 0.783(13) 1 calc GR . P A 1
H1B H 0.215383 1.210472 0.991843 0.074 Uiso 0.783(13) 1 calc GR . P A 1
H1C H 0.050512 1.098414 0.953597 0.074 Uiso 0.783(13) 1 calc GR . P A 1
C1A C 0.147(5) 1.142(4) 0.937(4) 0.034(4) Uani 0.217(13) 1 d D U P A 2
H1AA H 0.155980 1.212919 0.880266 0.052 Uiso 0.217(13) 1 calc GR . P A 2
H1AB H 0.215920 1.187390 1.038995 0.052 Uiso 0.217(13) 1 calc GR . P A 2
H1AC H 0.034700 1.114798 0.921060 0.052 Uiso 0.217(13) 1 calc GR . P A 2
C2 C 0.3051(3) 1.0242(2) 0.8370(3) 0.0360(5) Uani 1 1 d D U . . .
C3 C 0.5780(3) 0.9933(3) 0.7327(3) 0.0483(6) Uani 1 1 d . . . . .
H3A H 0.531928 1.082088 0.725464 0.072 Uiso 1 1 calc GR . . . .
H3B H 0.582858 0.953279 0.642665 0.072 Uiso 1 1 calc GR . . . .
H3C H 0.687264 1.019293 0.811632 0.072 Uiso 1 1 calc GR . . . .
C4 C 0.4748(3) 0.8802(2) 0.7606(2) 0.0323(5) Uani 1 1 d . . . . .
C5 C 0.3552(2) 0.8878(2) 0.8012(2) 0.0291(4) Uani 1 1 d . . . . .
C6 C 0.2781(2) 0.73272(19) 0.7947(2) 0.0249(4) Uani 1 1 d . . . . .
H6 H 0.257083 0.730894 0.880454 0.030 Uiso 1 1 calc R . . . .
C7 C 0.4173(2) 0.65521(19) 0.8014(2) 0.0258(4) Uani 1 1 d . . . . .
H7 H 0.490983 0.665549 0.904707 0.031 Uiso 1 1 calc R . . . .
C8 C -0.1031(3) 0.7409(3) 0.7234(3) 0.0468(6) Uani 1 1 d . . . . .
H8A H -0.178748 0.644532 0.679285 0.070 Uiso 1 1 calc GR . . . .
H8B H -0.163721 0.819811 0.721561 0.070 Uiso 1 1 calc GR . . . .
H8C H -0.030456 0.743905 0.822910 0.070 Uiso 1 1 calc GR . . . .
C9 C -0.0060(3) 0.7628(3) 0.6415(2) 0.0368(5) Uani 1 1 d . . . . .
C10 C 0.1203(2) 0.6718(2) 0.6541(2) 0.0332(5) Uani 1 1 d . . . . .
H10A H 0.145912 0.669752 0.571258 0.040 Uiso 1 1 calc R . . . .
H10B H 0.075548 0.568626 0.650125 0.040 Uiso 1 1 calc R . . . .
C11 C 0.3774(2) 0.4928(2) 0.7248(2) 0.0269(4) Uani 1 1 d . . . . .
H11 H 0.303461 0.479950 0.621112 0.032 Uiso 1 1 calc R . . . .
C12 C 0.5278(2) 0.43638(19) 0.7375(2) 0.0270(4) Uani 1 1 d . . . . .
C13 C 0.5428(3) 0.3736(2) 0.6154(2) 0.0331(5) Uani 1 1 d . . . . .
H13 H 0.457184 0.363980 0.523302 0.040 Uiso 1 1 calc R . . . .
C14 C 0.6822(3) 0.3247(3) 0.6272(3) 0.0428(5) Uani 1 1 d . . . . .
H14 H 0.691221 0.281515 0.543046 0.051 Uiso 1 1 calc R . . . .
C15 C 0.8078(3) 0.3385(3) 0.7604(3) 0.0464(6) Uani 1 1 d . . . . .
H15 H 0.904171 0.307246 0.768057 0.056 Uiso 1 1 calc R . . . .
C16 C 0.7923(3) 0.3983(3) 0.8828(3) 0.0419(5) Uani 1 1 d . . . . .
H16 H 0.877573 0.406121 0.974683 0.050 Uiso 1 1 calc R . . . .
C17 C 0.6533(3) 0.4466(2) 0.8719(2) 0.0330(5) Uani 1 1 d . . . . .
H17 H 0.643281 0.486862 0.956347 0.040 Uiso 1 1 calc R . . . .
N1 N -0.0131(3) 0.8612(3) 0.5668(2) 0.0488(5) Uani 1 1 d . . . . .
O1 O 0.3600(5) 1.1481(3) 0.8309(6) 0.0408(10) Uani 0.783(13) 1 d . U P A 1
O1A O 0.296(2) 1.1173(13) 0.758(2) 0.042(3) Uani 0.217(13) 1 d . U P A 2
O2 O 0.2039(19) 1.0032(14) 0.897(2) 0.0328(13) Uani 0.783(13) 1 d D U P A 1
O2A O 0.199(7) 1.012(5) 0.894(8) 0.036(4) Uani 0.217(13) 1 d D U P A 2
O3 O 0.50511(17) 0.74146(14) 0.74146(16) 0.0315(3) Uani 1 1 d . . . . .
O4 O -0.1273(3) 0.9487(3) 0.5680(2) 0.0683(6) Uani 1 1 d . . . . .
H4 H -0.128001 1.010656 0.518552 0.102 Uiso 1 1 calc GR . . . .
O5 O 0.29263(18) 0.41919(15) 0.79051(17) 0.0352(4) Uani 1 1 d . . . . .
H5 H 0.300224 0.329940 0.780169 0.053 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 O2 1.443(6) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
C1A O2A 1.438(17) . ?
C2 C5 1.455(3) . ?
C2 O1 1.230(3) . ?
C2 O1A 1.289(11) . ?
C2 O2 1.343(5) . ?
C2 O2A 1.345(16) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3 C4 1.485(3) . ?
C4 C5 1.346(3) . ?
C4 O3 1.363(2) . ?
C5 C6 1.515(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.539(2) . ?
C6 C10 1.550(3) . ?
C7 H7 1.0000 . ?
C7 C11 1.520(3) . ?
C7 O3 1.462(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 C9 1.496(3) . ?
C9 C10 1.506(3) . ?
C9 N1 1.298(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11 1.0000 . ?
C11 C12 1.514(3) . ?
C11 O5 1.427(2) . ?
C12 C13 1.389(3) . ?
C12 C17 1.395(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(3) . ?
C17 H17 0.9500 . ?
N1 O4 1.418(3) . ?
O4 H4 0.8400 . ?
O5 H5 0.8400 . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
O2A C1A H1AA 109.5 . . ?
O2A C1A H1AB 109.5 . . ?
O2A C1A H1AC 109.5 . . ?
O1 C2 C5 126.2(2) . . ?
O1 C2 O2 122.2(6) . . ?
O1A C2 C5 117.9(5) . . ?
O1A C2 O2A 119(3) . . ?
O2 C2 C5 111.0(5) . . ?
O2A C2 C5 115(2) . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
C5 C4 C3 132.29(19) . . ?
C5 C4 O3 112.92(17) . . ?
O3 C4 C3 114.79(18) . . ?
C2 C5 C6 126.70(18) . . ?
C4 C5 C2 124.18(18) . . ?
C4 C5 C6 109.03(17) . . ?
C5 C6 H6 110.9 . . ?
C5 C6 C7 98.89(14) . . ?
C5 C6 C10 110.66(16) . . ?
C7 C6 H6 110.9 . . ?
C7 C6 C10 114.00(15) . . ?
C10 C6 H6 110.9 . . ?
C6 C7 H7 107.9 . . ?
C11 C7 C6 118.99(16) . . ?
C11 C7 H7 107.9 . . ?
O3 C7 C6 105.09(13) . . ?
O3 C7 H7 107.9 . . ?
O3 C7 C11 108.67(15) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
C8 C9 C10 118.2(2) . . ?
N1 C9 C8 125.6(2) . . ?
N1 C9 C10 116.1(2) . . ?
C6 C10 H10A 109.0 . . ?
C6 C10 H10B 109.0 . . ?
C9 C10 C6 112.81(16) . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C7 C11 H11 109.2 . . ?
C12 C11 C7 111.91(16) . . ?
C12 C11 H11 109.2 . . ?
O5 C11 C7 104.20(15) . . ?
O5 C11 H11 109.2 . . ?
O5 C11 C12 113.01(15) . . ?
C13 C12 C11 120.44(18) . . ?
C13 C12 C17 119.01(19) . . ?
C17 C12 C11 120.56(18) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.5(2) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.3(2) . . ?
C16 C17 H17 119.9 . . ?
C9 N1 O4 112.6(2) . . ?
C2 O2 C1 114.9(10) . . ?
C2 O2A C1A 119(3) . . ?
C4 O3 C7 106.38(14) . . ?
N1 O4 H4 109.5 . . ?
C11 O5 H5 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
C2 C5 C6 C7 -162.4(2) . . . . ?
C2 C5 C6 C10 77.7(3) . . . . ?
C3 C4 C5 C2 -4.1(4) . . . . ?
C3 C4 C5 C6 172.8(2) . . . . ?
C3 C4 O3 C7 168.67(19) . . . . ?
C4 C5 C6 C7 20.9(2) . . . . ?
C4 C5 C6 C10 -99.1(2) . . . . ?
C5 C2 O2 C1 -172.4(11) . . . . ?
C5 C2 O2A C1A 178(4) . . . . ?
C5 C4 O3 C7 -11.6(2) . . . . ?
C5 C6 C7 C11 -148.62(17) . . . . ?
C5 C6 C7 O3 -26.72(18) . . . . ?
C5 C6 C10 C9 -61.7(2) . . . . ?
C6 C7 C11 C12 177.69(15) . . . . ?
C6 C7 C11 O5 -59.9(2) . . . . ?
C6 C7 O3 C4 24.69(19) . . . . ?
C7 C6 C10 C9 -172.11(16) . . . . ?
C7 C11 C12 C13 -123.27(19) . . . . ?
C7 C11 C12 C17 56.8(2) . . . . ?
C8 C9 C10 C6 -79.0(2) . . . . ?
C8 C9 N1 O4 -0.7(3) . . . . ?
C10 C6 C7 C11 -31.2(2) . . . . ?
C10 C6 C7 O3 90.70(18) . . . . ?
C10 C9 N1 O4 -176.04(19) . . . . ?
C11 C7 O3 C4 153.07(16) . . . . ?
C11 C12 C13 C14 178.64(18) . . . . ?
C11 C12 C17 C16 -178.32(18) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C12 C17 C16 1.7(3) . . . . ?
C13 C14 C15 C16 1.6(4) . . . . ?
C14 C15 C16 C17 -1.3(4) . . . . ?
C15 C16 C17 C12 -0.4(3) . . . . ?
C17 C12 C13 C14 -1.4(3) . . . . ?
N1 C9 C10 C6 96.7(2) . . . . ?
O1 C2 C5 C4 2.5(5) . . . . ?
O1 C2 C5 C6 -173.8(4) . . . . ?
O1 C2 O2 C1 16(2) . . . . ?
O1A C2 C5 C4 41.3(10) . . . . ?
O1A C2 C5 C6 -135.0(10) . . . . ?
O1A C2 O2A C1A -35(7) . . . . ?
O2 C2 C5 C4 -169.1(10) . . . . ?
O2 C2 C5 C6 14.6(10) . . . . ?
O2A C2 C5 C4 -171(4) . . . . ?
O2A C2 C5 C6 13(4) . . . . ?
O3 C4 C5 C2 176.21(19) . . . . ?
O3 C4 C5 C6 -6.9(3) . . . . ?
O3 C7 C11 C12 57.6(2) . . . . ?
O3 C7 C11 O5 -179.95(14) . . . . ?
O5 C11 C12 C13 119.46(19) . . . . ?
O5 C11 C12 C17 -60.5(2) . . . . ?

_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_11_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2206605'
loop_
_audit_author_name
_audit_author_address
'chengyu yu'
;shihezhi University
China
;
_audit_update_record             
;
2022-09-12 deposited with the CCDC.	2023-10-06 downloaded from the CCDC.
;
_audit_creation_date             2022-06-07
_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         'C23 H24 O5'
_chemical_formula_sum            'C23 H24 O5'
_chemical_formula_weight         380.42
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2814(3)
_cell_length_b                   10.4848(3)
_cell_length_c                   11.7654(3)
_cell_angle_alpha                64.1770(10)
_cell_angle_beta                 78.3730(10)
_cell_angle_gamma                76.2590(10)
_cell_volume                     994.79(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.194
_cell_measurement_theta_min      4.897
_shelx_estimated_absorpt_T_max   0.912
_shelx_estimated_absorpt_T_min   0.863
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1071 before and 0.0620 after correction.
The Ratio of minimum to maximum transmission is 0.8936.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25216
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.265
_diffrn_reflns_theta_min         4.897
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3150
_reflns_number_total             3608
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3608
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.203
_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)+(0.0585P)²+0.4045P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1252
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C23) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C22(H22A,H22B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C23(H23A,H23B,H23C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
C1 C 0.58886(17) 0.19654(16) 0.55584(15) 0.0330(3) Uani 1 1 d . . . . .
C2 C 0.5850(2) 0.23579(19) 0.65507(17) 0.0427(4) Uani 1 1 d . . . . .
H2 H 0.533801 0.327696 0.650096 0.051 Uiso 1 1 calc R . . . .
C3 C 0.6559(2) 0.1410(2) 0.76140(18) 0.0505(5) Uani 1 1 d . . . . .
H3 H 0.651591 0.168004 0.829471 0.061 Uiso 1 1 calc R . . . .
C4 C 0.7326(2) 0.00768(19) 0.76937(17) 0.0473(4) Uani 1 1 d . . . . .
H4 H 0.781578 -0.056335 0.842195 0.057 Uiso 1 1 calc R . . . .
C5 C 0.7376(2) -0.03172(18) 0.67137(17) 0.0435(4) Uani 1 1 d . . . . .
H5 H 0.790896 -0.122848 0.675891 0.052 Uiso 1 1 calc R . . . .
C6 C 0.66484(18) 0.06140(17) 0.56609(16) 0.0381(4) Uani 1 1 d . . . . .
H6 H 0.666894 0.032427 0.499619 0.046 Uiso 1 1 calc R . . . .
C7 C 0.51915(17) 0.29824(16) 0.43554(15) 0.0332(3) Uani 1 1 d . . . . .
H7 H 0.535149 0.248208 0.377391 0.040 Uiso 1 1 calc R . . . .
C8 C 0.35357(16) 0.35345(16) 0.45526(15) 0.0318(3) Uani 1 1 d . . . . .
H8 H 0.338911 0.412336 0.505770 0.038 Uiso 1 1 calc R . . . .
C9 C 0.27479(16) 0.44340(16) 0.33421(14) 0.0318(3) Uani 1 1 d . . . . .
H9 H 0.268421 0.548629 0.309069 0.038 Uiso 1 1 calc R . . . .
C10 C 0.12265(17) 0.39895(18) 0.38539(15) 0.0358(4) Uani 1 1 d . . . . .
C11 C 0.13477(17) 0.27592(18) 0.48964(15) 0.0365(4) Uani 1 1 d . . . . .
C12 C 0.0258(2) 0.1796(2) 0.57023(19) 0.0528(5) Uani 1 1 d . . . . .
H12A H -0.072577 0.222128 0.539784 0.079 Uiso 1 1 calc GR . . . .
H12B H 0.019619 0.167200 0.658481 0.079 Uiso 1 1 calc GR . . . .
H12C H 0.058515 0.085763 0.565597 0.079 Uiso 1 1 calc GR . . . .
C13 C 0.34848(17) 0.40090(17) 0.22273(15) 0.0350(4) Uani 1 1 d . . . . .
H13A H 0.446777 0.432651 0.192420 0.042 Uiso 1 1 calc R . . . .
H13B H 0.366383 0.294776 0.254625 0.042 Uiso 1 1 calc R . . . .
C14 C 0.25764(18) 0.46362(17) 0.11123(15) 0.0371(4) Uani 1 1 d . . . . .
C15 C 0.27615(18) 0.60672(17) 0.00660(15) 0.0376(4) Uani 1 1 d . . . . .
C16 C 0.1902(2) 0.6610(2) -0.09426(17) 0.0479(4) Uani 1 1 d . . . . .
H16 H 0.121486 0.607102 -0.094857 0.057 Uiso 1 1 calc R . . . .
C17 C 0.2049(3) 0.7932(2) -0.19364(18) 0.0576(5) Uani 1 1 d . . . . .
H17 H 0.146942 0.829139 -0.262571 0.069 Uiso 1 1 calc R . . . .
C18 C 0.3027(3) 0.8725(2) -0.19295(18) 0.0593(6) Uani 1 1 d . . . . .
H18 H 0.311430 0.963581 -0.260861 0.071 Uiso 1 1 calc R . . . .
C19 C 0.3885(2) 0.8203(2) -0.09383(19) 0.0543(5) Uani 1 1 d . . . . .
H19 H 0.456183 0.875409 -0.093722 0.065 Uiso 1 1 calc R . . . .
C20 C 0.3760(2) 0.68731(19) 0.00581(17) 0.0431(4) Uani 1 1 d . . . . .
H20 H 0.435769 0.651345 0.073565 0.052 Uiso 1 1 calc R . . . .
C21 C -0.01376(19) 0.4722(2) 0.32692(18) 0.0481(4) Uani 1 1 d . . . . .
C22 C -0.1306(3) 0.6881(3) 0.1735(3) 0.0873(9) Uani 1 1 d . . . . .
H22A H -0.220334 0.690718 0.234882 0.105 Uiso 1 1 calc R . . . .
H22B H -0.149157 0.645494 0.118518 0.105 Uiso 1 1 calc R . . . .
C23 C -0.0958(4) 0.8365(3) 0.0949(3) 0.0976(9) Uani 1 1 d . U . . .
H23A H -0.012767 0.833294 0.029348 0.146 Uiso 1 1 calc GR . . . .
H23B H -0.067884 0.873297 0.149556 0.146 Uiso 1 1 calc GR . . . .
H23C H -0.183903 0.899856 0.054445 0.146 Uiso 1 1 calc GR . . . .
O1 O 0.57937(12) 0.42787(12) 0.37024(12) 0.0428(3) Uani 1 1 d . . . . .
H1 H 0.673011 0.408298 0.364273 0.064 Uiso 1 1 calc GR . . . .
O2 O 0.27441(12) 0.23119(12) 0.52760(10) 0.0377(3) Uani 1 1 d . . . . .
O3 O 0.17022(15) 0.39525(14) 0.10749(13) 0.0526(4) Uani 1 1 d . . . . .
O4 O -0.00108(14) 0.60489(15) 0.23971(13) 0.0543(4) Uani 1 1 d . . . . .
O5 O -0.12720(16) 0.4228(2) 0.35329(17) 0.0899(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.389(2) . ?
C1 C6 1.389(2) . ?
C1 C7 1.512(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.517(2) . ?
C7 O1 1.4241(19) . ?
C8 H8 1.0000 . ?
C8 C9 1.541(2) . ?
C8 O2 1.4671(18) . ?
C9 H9 1.0000 . ?
C9 C10 1.516(2) . ?
C9 C13 1.546(2) . ?
C10 C11 1.338(2) . ?
C10 C21 1.447(2) . ?
C11 C12 1.486(2) . ?
C11 O2 1.3642(19) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.515(2) . ?
C14 C15 1.491(2) . ?
C14 O3 1.222(2) . ?
C15 C16 1.395(2) . ?
C15 C20 1.391(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.372(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.380(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(3) . ?
C20 H20 0.9500 . ?
C21 O4 1.337(2) . ?
C21 O5 1.209(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.498(4) . ?
C22 O4 1.450(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O1 H1 0.8400 . ?

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
C2 C1 C6 118.49(15) . . ?
C2 C1 C7 122.12(14) . . ?
C6 C1 C7 119.33(14) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.09(16) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.68(17) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.60(16) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.95(16) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.17(16) . . ?
C5 C6 H6 119.4 . . ?
C1 C7 H7 108.7 . . ?
C1 C7 C8 114.86(13) . . ?
C8 C7 H7 108.7 . . ?
O1 C7 C1 113.36(12) . . ?
O1 C7 H7 108.7 . . ?
O1 C7 C8 102.35(12) . . ?
C7 C8 H8 108.5 . . ?
C7 C8 C9 116.35(13) . . ?
C9 C8 H8 108.5 . . ?
O2 C8 C7 109.38(12) . . ?
O2 C8 H8 108.5 . . ?
O2 C8 C9 105.27(11) . . ?
C8 C9 H9 111.1 . . ?
C8 C9 C13 112.54(12) . . ?
C10 C9 C8 98.69(12) . . ?
C10 C9 H9 111.1 . . ?
C10 C9 C13 111.74(12) . . ?
C13 C9 H9 111.1 . . ?
C11 C10 C9 109.54(13) . . ?
C11 C10 C21 124.63(15) . . ?
C21 C10 C9 125.72(15) . . ?
C10 C11 C12 132.18(15) . . ?
C10 C11 O2 113.17(13) . . ?
O2 C11 C12 114.65(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 108.7 . . ?
C9 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 C9 114.42(13) . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C15 C14 C13 120.21(14) . . ?
O3 C14 C13 119.32(15) . . ?
O3 C14 C15 120.46(15) . . ?
C16 C15 C14 118.49(16) . . ?
C20 C15 C14 122.47(15) . . ?
C20 C15 C16 119.03(16) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.19(19) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.33(19) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.14(18) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.9 . . ?
C19 C20 C15 120.14(18) . . ?
C19 C20 H20 119.9 . . ?
O4 C21 C10 111.65(15) . . ?
O5 C21 C10 125.30(19) . . ?
O5 C21 O4 123.04(17) . . ?
H22A C22 H22B 108.7 . . ?
C23 C22 H22A 110.5 . . ?
C23 C22 H22B 110.5 . . ?
O4 C22 H22A 110.5 . . ?
O4 C22 H22B 110.5 . . ?
O4 C22 C23 106.2(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C7 O1 H1 109.5 . . ?
C11 O2 C8 105.97(11) . . ?
C21 O4 C22 116.58(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C12 H12A O5 0.98 2.33 3.017(3) 126.7 . yes
C13 H13A O1 0.99 2.61 3.146(2) 114.1 . yes
O1 H1 O5 0.84 1.87 2.6797(18) 161.3 1_655 yes

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
C1 C2 C3 C4 0.9(3) . . . . ?
C1 C7 C8 C9 -173.27(12) . . . . ?
C1 C7 C8 O2 -54.21(17) . . . . ?
C2 C1 C6 C5 -1.1(2) . . . . ?
C2 C1 C7 C8 -58.2(2) . . . . ?
C2 C1 C7 O1 59.0(2) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 1.5(3) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C6 C1 C7 C8 124.53(16) . . . . ?
C6 C1 C7 O1 -118.29(16) . . . . ?
C7 C1 C2 C3 -177.32(16) . . . . ?
C7 C1 C6 C5 176.22(15) . . . . ?
C7 C8 C9 C10 147.26(13) . . . . ?
C7 C8 C9 C13 29.27(18) . . . . ?
C7 C8 O2 C11 -150.51(13) . . . . ?
C8 C9 C10 C11 -19.54(16) . . . . ?
C8 C9 C10 C21 164.13(17) . . . . ?
C8 C9 C13 C14 168.01(13) . . . . ?
C9 C8 O2 C11 -24.79(15) . . . . ?
C9 C10 C11 C12 -174.10(19) . . . . ?
C9 C10 C11 O2 5.4(2) . . . . ?
C9 C10 C21 O4 -16.2(3) . . . . ?
C9 C10 C21 O5 164.8(2) . . . . ?
C9 C13 C14 C15 89.25(17) . . . . ?
C9 C13 C14 O3 -91.38(19) . . . . ?
C10 C9 C13 C14 58.03(17) . . . . ?
C10 C11 O2 C8 12.62(18) . . . . ?
C10 C21 O4 C22 179.23(18) . . . . ?
C11 C10 C21 O4 168.04(16) . . . . ?
C11 C10 C21 O5 -10.9(3) . . . . ?
C12 C11 O2 C8 -167.81(15) . . . . ?
C13 C9 C10 C11 99.04(16) . . . . ?
C13 C9 C10 C21 -77.3(2) . . . . ?
C13 C14 C15 C16 -179.86(15) . . . . ?
C13 C14 C15 C20 0.4(2) . . . . ?
C14 C15 C16 C17 -179.63(16) . . . . ?
C14 C15 C20 C19 -179.77(15) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C16 C15 C20 C19 0.5(3) . . . . ?
C16 C17 C18 C19 0.7(3) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C18 C19 C20 C15 -0.5(3) . . . . ?
C20 C15 C16 C17 0.1(3) . . . . ?
C21 C10 C11 C12 2.3(3) . . . . ?
C21 C10 C11 O2 -178.26(16) . . . . ?
C23 C22 O4 C21 172.79(19) . . . . ?
O1 C7 C8 C9 63.44(16) . . . . ?
O1 C7 C8 O2 -177.49(11) . . . . ?
O2 C8 C9 C10 25.98(14) . . . . ?
O2 C8 C9 C13 -92.00(14) . . . . ?
O3 C14 C15 C16 0.8(2) . . . . ?
O3 C14 C15 C20 -178.96(16) . . . . ?
O5 C21 O4 C22 -1.8(3) . . . . ?

_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_11_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2206567'
loop_
_audit_author_name
_audit_author_address
'chengyu yu'
;shihezhi university
China
;
_audit_update_record             
;
2022-09-12 deposited with the CCDC.	2023-10-06 downloaded from the CCDC.
;
_audit_creation_date             2021-12-30
_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         'C18 H22 O5'
_chemical_formula_sum            'C18 H22 O5'
_chemical_formula_weight         318.35
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2088(4)
_cell_length_b                   9.7622(4)
_cell_length_c                   21.0942(8)
_cell_angle_alpha                78.302(2)
_cell_angle_beta                 89.303(2)
_cell_angle_gamma                64.9750(10)
_cell_volume                     1676.82(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.15
_cell_measurement_theta_min      5.32
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.902
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.7042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0841 before and 0.0567 after correction. The Ratio of minimum to maximum transmission is 0.9351. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40488
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.200
_diffrn_reflns_theta_min         2.146
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5571
_reflns_number_total             6072
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       APEX3
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         6072
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.031
_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)+(0.0432P)²+0.6225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0961
_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:
 C7(H7), C8(H8), C9(H9), C25(H25), C26(H26), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C17(H17A,H17B), C30(H30A,H30B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6A), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C32(H32A,H32B,
 H32C), C34(H34A,H34B,H34C), C36(H36A,H36B,H36C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O6(H6)
;
_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
C1 C 0.36546(15) 0.52017(15) 0.34764(6) 0.0289(3) Uani 1 1 d . . . . .
C2 C 0.33483(17) 0.67444(16) 0.34259(7) 0.0356(3) Uani 1 1 d . . . . .
H2 H 0.268076 0.730914 0.371778 0.043 Uiso 1 1 calc R . . . .
C3 C 0.4010(2) 0.74655(19) 0.29525(8) 0.0458(4) Uani 1 1 d . . . . .
H3 H 0.378916 0.852137 0.291964 0.055 Uiso 1 1 calc R . . . .
C4 C 0.4990(2) 0.6649(2) 0.25296(8) 0.0524(4) Uani 1 1 d . . . . .
H4 H 0.544007 0.714319 0.220474 0.063 Uiso 1 1 calc R . . . .
C5 C 0.5313(2) 0.5119(2) 0.25792(8) 0.0503(4) Uani 1 1 d . . . . .
H5 H 0.599782 0.455271 0.229192 0.060 Uiso 1 1 calc R . . . .
C6 C 0.46396(17) 0.44005(18) 0.30480(7) 0.0375(3) Uani 1 1 d . . . . .
H6A H 0.485683 0.334744 0.307530 0.045 Uiso 1 1 calc R . . . .
C7 C 0.29403(15) 0.44173(15) 0.39973(6) 0.0277(3) Uani 1 1 d . . . . .
H7 H 0.318508 0.336623 0.392100 0.033 Uiso 1 1 calc R . . . .
C8 C 0.36973(14) 0.42163(15) 0.46726(6) 0.0262(3) Uani 1 1 d . . . . .
H8 H 0.360912 0.523919 0.473103 0.031 Uiso 1 1 calc R . . . .
C9 C 0.29812(15) 0.35164(14) 0.52437(6) 0.0268(3) Uani 1 1 d . . . . .
H9 H 0.202194 0.341611 0.508225 0.032 Uiso 1 1 calc R . . . .
C10 C 0.43628(15) 0.19263(14) 0.54782(6) 0.0281(3) Uani 1 1 d . . . . .
C11 C 0.56586(16) 0.18336(15) 0.51606(6) 0.0289(3) Uani 1 1 d . . . . .
C12 C 0.25402(16) 0.44449(15) 0.57766(6) 0.0295(3) Uani 1 1 d . . . . .
H12A H 0.211985 0.391301 0.612960 0.035 Uiso 1 1 calc R . . . .
H12B H 0.353650 0.442357 0.595936 0.035 Uiso 1 1 calc R . . . .
C13 C 0.13284(15) 0.61037(15) 0.55747(7) 0.0307(3) Uani 1 1 d . . . . .
C14 C 0.0894(2) 0.70050(18) 0.60973(8) 0.0451(4) Uani 1 1 d . . . . .
H14A H 0.052626 0.810937 0.590270 0.068 Uiso 1 1 calc GR . . . .
H14B H 0.183933 0.665418 0.640218 0.068 Uiso 1 1 calc GR . . . .
H14C H 0.003273 0.684247 0.632961 0.068 Uiso 1 1 calc GR . . . .
C15 C 0.42901(16) 0.06925(15) 0.59778(7) 0.0311(3) Uani 1 1 d . . . . .
C16 C 0.73230(17) 0.05831(17) 0.52263(8) 0.0381(3) Uani 1 1 d . . . . .
H16A H 0.752043 0.015738 0.483452 0.057 Uiso 1 1 calc GR . . . .
H16B H 0.745172 -0.024008 0.560538 0.057 Uiso 1 1 calc GR . . . .
H16C H 0.809347 0.100805 0.528226 0.057 Uiso 1 1 calc GR . . . .
C17 C 0.25076(19) -0.01002(18) 0.66011(8) 0.0419(4) Uani 1 1 d . . . . .
H17A H 0.307376 -0.031081 0.703056 0.050 Uiso 1 1 calc R . . . .
H17B H 0.291330 -0.107438 0.644302 0.050 Uiso 1 1 calc R . . . .
C18 C 0.0729(2) 0.0512(2) 0.66522(9) 0.0479(4) Uani 1 1 d . . . . .
H18A H 0.018516 0.072097 0.622344 0.072 Uiso 1 1 calc GR . . . .
H18B H 0.034629 0.147241 0.681092 0.072 Uiso 1 1 calc GR . . . .
H18C H 0.049350 -0.025726 0.695560 0.072 Uiso 1 1 calc GR . . . .
O1 O 0.12331(11) 0.52724(12) 0.39634(5) 0.0344(2) Uani 1 1 d . . . . .
H1 H 0.099143 0.581255 0.424527 0.052 Uiso 1 1 calc GR . . . .
O2 O 0.54061(10) 0.31322(10) 0.47024(4) 0.0304(2) Uani 1 1 d . . . . .
O3 O 0.53936(13) -0.05421(11) 0.62208(5) 0.0426(3) Uani 1 1 d . . . . .
O4 O 0.27714(12) 0.10821(11) 0.61453(5) 0.0360(2) Uani 1 1 d . . . . .
O5 O 0.07271(12) 0.67150(11) 0.50188(5) 0.0369(2) Uani 1 1 d . . . . .
C19 C 0.89893(16) 0.44535(15) 0.15445(6) 0.0282(3) Uani 1 1 d . . . . .
C20 C 0.93878(18) 0.51568(18) 0.19793(7) 0.0375(3) Uani 1 1 d . . . . .
H20 H 0.872394 0.621244 0.197905 0.045 Uiso 1 1 calc R . . . .
C21 C 1.0744(2) 0.4339(2) 0.24152(8) 0.0489(4) Uani 1 1 d . . . . .
H21 H 1.100750 0.484024 0.270663 0.059 Uiso 1 1 calc R . . . .
C22 C 1.1707(2) 0.2806(2) 0.24260(8) 0.0505(4) Uani 1 1 d . . . . .
H22 H 1.262647 0.224442 0.272798 0.061 Uiso 1 1 calc R . . . .
C23 C 1.13299(19) 0.20826(19) 0.19949(8) 0.0453(4) Uani 1 1 d . . . . .
H23 H 1.199406 0.102479 0.199926 0.054 Uiso 1 1 calc R . . . .
C24 C 0.99825(17) 0.29060(16) 0.15574(7) 0.0350(3) Uani 1 1 d . . . . .
H24 H 0.973331 0.240556 0.126162 0.042 Uiso 1 1 calc R . . . .
C25 C 0.75366(15) 0.53331(15) 0.10534(6) 0.0266(3) Uani 1 1 d . . . . .
H25 H 0.685733 0.634193 0.117263 0.032 Uiso 1 1 calc R . . . .
C26 C 0.80555(14) 0.56738(14) 0.03682(6) 0.0244(3) Uani 1 1 d . . . . .
H26 H 0.885214 0.468372 0.026571 0.029 Uiso 1 1 calc R . . . .
C27 C 0.66709(15) 0.64941(14) -0.01769(6) 0.0246(3) Uani 1 1 d . . . . .
H27 H 0.563065 0.657903 -0.000035 0.029 Uiso 1 1 calc R . . . .
C28 C 0.66668(15) 0.80811(14) -0.03660(6) 0.0260(3) Uani 1 1 d . . . . .
C29 C 0.79255(15) 0.80814(14) -0.00568(6) 0.0269(3) Uani 1 1 d . . . . .
C30 C 0.69847(16) 0.57022(14) -0.07547(6) 0.0274(3) Uani 1 1 d . . . . .
H30A H 0.606896 0.631221 -0.108805 0.033 Uiso 1 1 calc R . . . .
H30B H 0.795605 0.574155 -0.094695 0.033 Uiso 1 1 calc R . . . .
C31 C 0.72168(15) 0.40485(15) -0.06097(6) 0.0283(3) Uani 1 1 d . . . . .
C32 C 0.7556(2) 0.32654(17) -0.11716(7) 0.0405(3) Uani 1 1 d . . . . .
H32A H 0.872073 0.268907 -0.118065 0.061 Uiso 1 1 calc GR . . . .
H32B H 0.711757 0.404625 -0.157746 0.061 Uiso 1 1 calc GR . . . .
H32C H 0.705219 0.254857 -0.112441 0.061 Uiso 1 1 calc GR . . . .
C33 C 0.55067(16) 0.94022(15) -0.08323(6) 0.0290(3) Uani 1 1 d . . . . .
C34 C 0.85306(18) 0.92858(16) -0.01033(7) 0.0363(3) Uani 1 1 d . . . . .
H34A H 0.773791 1.017436 0.004911 0.054 Uiso 1 1 calc GR . . . .
H34B H 0.870549 0.962173 -0.055633 0.054 Uiso 1 1 calc GR . . . .
H34C H 0.954732 0.885558 0.016651 0.054 Uiso 1 1 calc GR . . . .
C35 C 0.30675(18) 1.03176(17) -0.14848(8) 0.0396(3) Uani 1 1 d . . . . .
H35A H 0.351138 1.057151 -0.189870 0.048 Uiso 1 1 calc R . . . .
H35B H 0.258200 1.125904 -0.130408 0.048 Uiso 1 1 calc R . . . .
C36 C 0.1831(2) 0.97496(19) -0.15952(8) 0.0452(4) Uani 1 1 d . . . . .
H36A H 0.094803 1.056147 -0.189845 0.068 Uiso 1 1 calc GR . . . .
H36B H 0.141219 0.949140 -0.118103 0.068 Uiso 1 1 calc GR . . . .
H36C H 0.232543 0.882506 -0.177823 0.068 Uiso 1 1 calc GR . . . .
O6 O 0.65970(11) 0.44831(11) 0.10666(4) 0.0326(2) Uani 1 1 d . . . . .
H6 H 0.677493 0.405510 0.074820 0.049 Uiso 1 1 calc GR . . . .
O7 O 0.88291(10) 0.67182(10) 0.03668(4) 0.0281(2) Uani 1 1 d . . . . .
O8 O 0.55411(13) 1.06442(11) -0.10269(5) 0.0416(3) Uani 1 1 d . . . . .
O9 O 0.43187(11) 0.90817(10) -0.10309(5) 0.0340(2) Uani 1 1 d . . . . .
O10 O 0.71688(12) 0.33477(11) -0.00653(5) 0.0341(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.391(2) . ?
C1 C6 1.385(2) . ?
C1 C7 1.5145(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(2) . ?
C6 H6A 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.5326(17) . ?
C7 O1 1.4289(15) . ?
C8 H8 1.0000 . ?
C8 C9 1.5431(18) . ?
C8 O2 1.4720(15) . ?
C9 H9 1.0000 . ?
C9 C10 1.5186(17) . ?
C9 C12 1.5298(18) . ?
C10 C11 1.3397(19) . ?
C10 C15 1.4553(19) . ?
C11 C16 1.4874(18) . ?
C11 O2 1.3619(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5007(18) . ?
C13 C14 1.495(2) . ?
C13 O5 1.2207(17) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 O3 1.2140(17) . ?
C15 O4 1.3482(17) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.498(2) . ?
C17 O4 1.4482(17) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O1 H1 0.8400 . ?
C19 C20 1.387(2) . ?
C19 C24 1.3909(19) . ?
C19 C25 1.5171(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.375(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(2) . ?
C24 H24 0.9500 . ?
C25 H25 1.0000 . ?
C25 C26 1.5332(17) . ?
C25 O6 1.4266(15) . ?
C26 H26 1.0000 . ?
C26 C27 1.5452(17) . ?
C26 O7 1.4698(14) . ?
C27 H27 1.0000 . ?
C27 C28 1.5178(16) . ?
C27 C30 1.5332(18) . ?
C28 C29 1.3371(19) . ?
C28 C33 1.4552(18) . ?
C29 C34 1.4862(18) . ?
C29 O7 1.3641(15) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.5016(17) . ?
C31 C32 1.4978(19) . ?
C31 O10 1.2224(16) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 O8 1.2124(16) . ?
C33 O9 1.3506(16) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.500(2) . ?
C35 O9 1.4430(16) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
O6 H6 0.8400 . ?

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
C2 C1 C7 120.31(12) . . ?
C6 C1 C2 118.64(13) . . ?
C6 C1 C7 121.04(12) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.54(15) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.04(16) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.89(15) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.15(16) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.73(15) . . ?
C1 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C1 C7 H7 108.2 . . ?
C1 C7 C8 110.65(10) . . ?
C8 C7 H7 108.2 . . ?
O1 C7 C1 110.85(10) . . ?
O1 C7 H7 108.2 . . ?
O1 C7 C8 110.55(10) . . ?
C7 C8 H8 109.3 . . ?
C7 C8 C9 114.95(10) . . ?
C9 C8 H8 109.3 . . ?
O2 C8 C7 107.30(10) . . ?
O2 C8 H8 109.3 . . ?
O2 C8 C9 106.45(9) . . ?
C8 C9 H9 110.3 . . ?
C10 C9 C8 101.07(10) . . ?
C10 C9 H9 110.3 . . ?
C10 C9 C12 111.76(10) . . ?
C12 C9 C8 112.88(10) . . ?
C12 C9 H9 110.3 . . ?
C11 C10 C9 109.94(11) . . ?
C11 C10 C15 125.15(12) . . ?
C15 C10 C9 124.92(12) . . ?
C10 C11 C16 131.66(13) . . ?
C10 C11 O2 113.85(11) . . ?
O2 C11 C16 114.48(12) . . ?
C9 C12 H12A 108.2 . . ?
C9 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
C13 C12 C9 116.20(11) . . ?
C13 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
C14 C13 C12 116.05(12) . . ?
O5 C13 C12 123.27(12) . . ?
O5 C13 C14 120.67(12) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 C10 127.28(13) . . ?
O3 C15 O4 122.24(13) . . ?
O4 C15 C10 110.47(11) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H17A C17 H17B 108.6 . . ?
C18 C17 H17A 110.4 . . ?
C18 C17 H17B 110.4 . . ?
O4 C17 H17A 110.4 . . ?
O4 C17 H17B 110.4 . . ?
O4 C17 C18 106.65(12) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 O1 H1 109.5 . . ?
C11 O2 C8 107.88(10) . . ?
C15 O4 C17 116.07(11) . . ?
C20 C19 C24 118.23(13) . . ?
C20 C19 C25 121.87(12) . . ?
C24 C19 C25 119.89(12) . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 120.91(15) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.20(16) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.77(14) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.86(15) . . ?
C24 C23 H23 120.1 . . ?
C19 C24 H24 119.5 . . ?
C23 C24 C19 121.04(14) . . ?
C23 C24 H24 119.5 . . ?
C19 C25 H25 108.4 . . ?
C19 C25 C26 110.78(10) . . ?
C26 C25 H25 108.4 . . ?
O6 C25 C19 110.59(10) . . ?
O6 C25 H25 108.4 . . ?
O6 C25 C26 110.29(10) . . ?
C25 C26 H26 109.2 . . ?
C25 C26 C27 115.10(10) . . ?
C27 C26 H26 109.2 . . ?
O7 C26 C25 107.52(10) . . ?
O7 C26 H26 109.2 . . ?
O7 C26 C27 106.50(9) . . ?
C26 C27 H27 110.4 . . ?
C28 C27 C26 101.00(9) . . ?
C28 C27 H27 110.4 . . ?
C28 C27 C30 111.26(10) . . ?
C30 C27 C26 113.00(10) . . ?
C30 C27 H27 110.4 . . ?
C29 C28 C27 110.02(11) . . ?
C29 C28 C33 124.40(11) . . ?
C33 C28 C27 125.55(11) . . ?
C28 C29 C34 131.52(12) . . ?
C28 C29 O7 113.86(11) . . ?
O7 C29 C34 114.60(11) . . ?
C27 C30 H30A 108.2 . . ?
C27 C30 H30B 108.2 . . ?
H30A C30 H30B 107.4 . . ?
C31 C30 C27 116.26(11) . . ?
C31 C30 H30A 108.2 . . ?
C31 C30 H30B 108.2 . . ?
C32 C31 C30 116.24(11) . . ?
O10 C31 C30 122.97(12) . . ?
O10 C31 C32 120.77(12) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O8 C33 C28 126.88(12) . . ?
O8 C33 O9 122.47(12) . . ?
O9 C33 C28 110.65(10) . . ?
C29 C34 H34A 109.5 . . ?
C29 C34 H34B 109.5 . . ?
C29 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
H35A C35 H35B 108.6 . . ?
C36 C35 H35A 110.4 . . ?
C36 C35 H35B 110.4 . . ?
O9 C35 H35A 110.4 . . ?
O9 C35 H35B 110.4 . . ?
O9 C35 C36 106.70(12) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C25 O6 H6 109.5 . . ?
C29 O7 C26 107.88(9) . . ?
C33 O9 C35 116.02(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
