# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_1
_audit_block_doi                 10.5517/ccdc.csd.cc2hyhkj
_database_code_depnum_ccdc_archive 'CCDC 2322258'
loop_
_audit_author_name
_audit_author_address
'xiaoliang xu'
;YNU
China
;
_audit_update_record             
;
2023-12-28 deposited with the CCDC.	2024-02-26 downloaded from the CCDC.
;
_audit_creation_date             2022-05-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H22 O4'
_chemical_formula_sum            'C16 H22 O4'
_chemical_formula_weight         278.33
_chemical_absolute_configuration AD
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.6552(16)
_cell_length_b                   5.6610(12)
_cell_length_c                   17.132(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.164(7)
_cell_angle_gamma                90
_cell_volume                     728.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7697
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      67.0956
_cell_measurement_theta_min      2.6289
_shelx_estimated_absorpt_T_max   0.805
_shelx_estimated_absorpt_T_min   0.768
_exptl_absorpt_coefficient_mu    0.733
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1508 before and 0.0909 after correction.
The Ratio of minimum to maximum transmission is 0.6931.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.31
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7551
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.090
_diffrn_reflns_theta_max         67.090
_diffrn_reflns_theta_min         2.629
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.924
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                2451
_reflns_number_total             2507
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1026 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2507
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0371
_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)+(0.0306P)²+0.2425P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0949
_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:
 C6(H6), C11(H11), C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3970(2) 0.5523(3) 0.42065(10) 0.0294(4) Uani 1 1 d . . . . .
O2 O 0.3176(2) 0.6992(3) 0.18835(10) 0.0304(4) Uani 1 1 d . . . . .
O3 O -0.0785(2) 0.3574(4) 0.30430(11) 0.0393(5) Uani 1 1 d . . . . .
O4 O 0.0960(2) 0.4667(3) 0.41722(10) 0.0312(4) Uani 1 1 d . . . . .
C1 C 0.2894(4) 0.5415(6) 0.54010(15) 0.0372(6) Uani 1 1 d . . . . .
H1A H 0.193377 0.590748 0.566928 0.056 Uiso 1 1 calc R U . . .
H1B H 0.400705 0.618606 0.565364 0.056 Uiso 1 1 calc R U . . .
H1C H 0.303950 0.369722 0.544213 0.056 Uiso 1 1 calc R U . . .
C2 C 0.2440(3) 0.6112(5) 0.45412(15) 0.0294(6) Uani 1 1 d . . . . .
C3 C 0.3650(3) 0.5546(5) 0.33945(14) 0.0263(5) Uani 1 1 d . . . . .
C4 C 0.2010(3) 0.5292(4) 0.29560(15) 0.0258(5) Uani 1 1 d . . . . .
C5 C 0.1747(3) 0.5513(5) 0.20504(14) 0.0276(5) Uani 1 1 d . . . . .
C6 C 0.2121(3) 0.3121(4) 0.16892(14) 0.0271(6) Uani 1 1 d . . . . .
H6 H 0.167326 0.179021 0.198028 0.033 Uiso 1 1 calc R U . . .
C7 C 0.1499(4) 0.2838(6) 0.07875(15) 0.0345(6) Uani 1 1 d . . . . .
H7A H 0.035832 0.196484 0.066306 0.041 Uiso 1 1 calc R U . . .
H7B H 0.134603 0.439647 0.052064 0.041 Uiso 1 1 calc R U . . .
C8 C 0.2992(3) 0.1439(5) 0.05305(15) 0.0340(6) Uani 1 1 d . . . . .
H8A H 0.294372 0.158556 -0.004909 0.041 Uiso 1 1 calc R U . . .
H8B H 0.293398 -0.025224 0.066982 0.041 Uiso 1 1 calc R U . . .
C9 C 0.2005(4) 0.8708(5) 0.44269(17) 0.0369(6) Uani 1 1 d . . . . .
H9A H 0.172895 0.907179 0.385707 0.055 Uiso 1 1 calc R U . . .
H9B H 0.303057 0.964877 0.468428 0.055 Uiso 1 1 calc R U . . .
H9C H 0.097411 0.908587 0.466530 0.055 Uiso 1 1 calc R U . . .
C10 C 0.5275(3) 0.5814(5) 0.30426(14) 0.0306(6) Uani 1 1 d . . . . .
H10A H 0.615488 0.458015 0.325574 0.037 Uiso 1 1 calc R U . . .
H10B H 0.582443 0.737807 0.318435 0.037 Uiso 1 1 calc R U . . .
C11 C 0.4753(3) 0.5586(5) 0.21429(14) 0.0275(5) Uani 1 1 d . . . . .
H11 H 0.574056 0.618473 0.189036 0.033 Uiso 1 1 calc R U . . .
C12 C 0.4203(3) 0.3093(4) 0.18286(15) 0.0270(5) Uani 1 1 d . . . . .
H12 H 0.471364 0.185203 0.222279 0.032 Uiso 1 1 calc R U . . .
C13 C 0.4666(3) 0.2607(5) 0.10052(14) 0.0293(6) Uani 1 1 d . . . . .
H13 H 0.480585 0.416962 0.075220 0.035 Uiso 1 1 calc R U . . .
C14 C 0.6389(4) 0.1245(5) 0.10397(17) 0.0369(6) Uani 1 1 d . . . . .
H14A H 0.624168 -0.036994 0.122312 0.055 Uiso 1 1 calc R U . . .
H14B H 0.735059 0.202836 0.140982 0.055 Uiso 1 1 calc R U . . .
H14C H 0.668498 0.119636 0.050852 0.055 Uiso 1 1 calc R U . . .
C15 C 0.0011(3) 0.6735(5) 0.16968(16) 0.0350(6) Uani 1 1 d . . . . .
H15A H -0.011097 0.817263 0.200012 0.052 Uiso 1 1 calc R U . . .
H15B H -0.098705 0.567072 0.172031 0.052 Uiso 1 1 calc R U . . .
H15C H 0.001025 0.714997 0.114137 0.052 Uiso 1 1 calc R U . . .
C16 C 0.0596(3) 0.4497(5) 0.33550(15) 0.0304(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
O1 C2 1.440(3) . ?
O1 C3 1.365(3) . ?
O2 C5 1.449(3) . ?
O2 C11 1.443(3) . ?
O3 C16 1.207(3) . ?
O4 C2 1.441(3) . ?
O4 C16 1.377(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.499(4) . ?
C2 C9 1.511(4) . ?
C3 C4 1.340(3) . ?
C3 C10 1.491(3) . ?
C4 C5 1.530(3) . ?
C4 C16 1.459(3) . ?
C5 C6 1.539(4) . ?
C5 C15 1.516(4) . ?
C6 H6 1.0000 . ?
C6 C7 1.534(3) . ?
C6 C12 1.565(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.524(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C13 1.529(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.521(3) . ?
C11 H11 1.0000 . ?
C11 C12 1.540(4) . ?
C12 H12 1.0000 . ?
C12 C13 1.544(4) . ?
C13 H13 1.0000 . ?
C13 C14 1.519(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 113.85(18) . . ?
C11 O2 C5 103.85(18) . . ?
C16 O4 C2 118.24(19) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 O4 108.97(19) . . ?
O1 C2 C1 106.2(2) . . ?
O1 C2 C9 110.5(2) . . ?
O4 C2 C1 107.2(2) . . ?
O4 C2 C9 111.2(2) . . ?
C1 C2 C9 112.7(2) . . ?
O1 C3 C10 114.4(2) . . ?
C4 C3 O1 122.3(2) . . ?
C4 C3 C10 123.3(2) . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 C16 118.1(2) . . ?
C16 C4 C5 122.4(2) . . ?
O2 C5 C4 106.92(19) . . ?
O2 C5 C6 102.86(19) . . ?
O2 C5 C15 107.1(2) . . ?
C4 C5 C6 109.7(2) . . ?
C15 C5 C4 112.0(2) . . ?
C15 C5 C6 117.2(2) . . ?
C5 C6 H6 110.7 . . ?
C5 C6 C12 102.18(19) . . ?
C7 C6 C5 116.8(2) . . ?
C7 C6 H6 110.7 . . ?
C7 C6 C12 105.14(19) . . ?
C12 C6 H6 110.7 . . ?
C6 C7 H7A 111.0 . . ?
C6 C7 H7B 111.0 . . ?
H7A C7 H7B 109.0 . . ?
C8 C7 C6 103.9(2) . . ?
C8 C7 H7A 111.0 . . ?
C8 C7 H7B 111.0 . . ?
C7 C8 H8A 111.2 . . ?
C7 C8 H8B 111.2 . . ?
C7 C8 C13 102.7(2) . . ?
H8A C8 H8B 109.1 . . ?
C13 C8 H8A 111.2 . . ?
C13 C8 H8B 111.2 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C10 H10A 109.9 . . ?
C3 C10 H10B 109.9 . . ?
C3 C10 C11 108.98(19) . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
O2 C11 C10 107.8(2) . . ?
O2 C11 H11 109.7 . . ?
O2 C11 C12 104.01(18) . . ?
C10 C11 H11 109.7 . . ?
C10 C11 C12 115.6(2) . . ?
C12 C11 H11 109.7 . . ?
C6 C12 H12 111.3 . . ?
C11 C12 C6 104.2(2) . . ?
C11 C12 H12 111.3 . . ?
C11 C12 C13 112.8(2) . . ?
C13 C12 C6 105.62(19) . . ?
C13 C12 H12 111.3 . . ?
C8 C13 C12 104.2(2) . . ?
C8 C13 H13 107.5 . . ?
C12 C13 H13 107.5 . . ?
C14 C13 C8 115.7(2) . . ?
C14 C13 C12 113.9(2) . . ?
C14 C13 H13 107.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 O4 117.9(2) . . ?
O3 C16 C4 126.3(2) . . ?
O4 C16 C4 115.6(2) . . ?

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
C10 H10A O3 0.99 2.50 3.272(3) 134.1 1_655 yes
C15 H15B O3 0.98 2.54 3.072(4) 114.3 . 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
O1 C3 C4 C5 175.7(2) . . . . ?
O1 C3 C4 C16 -12.6(4) . . . . ?
O1 C3 C10 C11 174.9(2) . . . . ?
O2 C5 C6 C7 -80.8(2) . . . . ?
O2 C5 C6 C12 33.3(2) . . . . ?
O2 C11 C12 C6 -20.9(2) . . . . ?
O2 C11 C12 C13 93.2(2) . . . . ?
C2 O1 C3 C4 -22.5(3) . . . . ?
C2 O1 C3 C10 158.9(2) . . . . ?
C2 O4 C16 O3 -169.5(2) . . . . ?
C2 O4 C16 C4 15.4(3) . . . . ?
C3 O1 C2 O4 51.0(3) . . . . ?
C3 O1 C2 C1 166.1(2) . . . . ?
C3 O1 C2 C9 -71.3(3) . . . . ?
C3 C4 C5 O2 -25.8(3) . . . . ?
C3 C4 C5 C6 85.0(3) . . . . ?
C3 C4 C5 C15 -142.9(3) . . . . ?
C3 C4 C16 O3 -158.3(3) . . . . ?
C3 C4 C16 O4 16.3(3) . . . . ?
C3 C10 C11 O2 45.4(3) . . . . ?
C3 C10 C11 C12 -70.4(3) . . . . ?
C4 C3 C10 C11 -3.7(4) . . . . ?
C4 C5 C6 C7 165.7(2) . . . . ?
C4 C5 C6 C12 -80.2(2) . . . . ?
C5 O2 C11 C10 -79.8(2) . . . . ?
C5 O2 C11 C12 43.4(2) . . . . ?
C5 C4 C16 O3 13.0(4) . . . . ?
C5 C4 C16 O4 -172.3(2) . . . . ?
C5 C6 C7 C8 141.0(2) . . . . ?
C5 C6 C12 C11 -7.5(2) . . . . ?
C5 C6 C12 C13 -126.6(2) . . . . ?
C6 C7 C8 C13 -42.4(3) . . . . ?
C6 C12 C13 C8 -21.7(3) . . . . ?
C6 C12 C13 C14 -148.8(2) . . . . ?
C7 C6 C12 C11 114.9(2) . . . . ?
C7 C6 C12 C13 -4.1(3) . . . . ?
C7 C8 C13 C12 39.6(3) . . . . ?
C7 C8 C13 C14 165.6(2) . . . . ?
C10 C3 C4 C5 -5.8(4) . . . . ?
C10 C3 C4 C16 165.9(2) . . . . ?
C10 C11 C12 C6 97.1(2) . . . . ?
C10 C11 C12 C13 -148.9(2) . . . . ?
C11 O2 C5 C4 66.9(2) . . . . ?
C11 O2 C5 C6 -48.7(2) . . . . ?
C11 O2 C5 C15 -172.9(2) . . . . ?
C11 C12 C13 C8 -134.9(2) . . . . ?
C11 C12 C13 C14 98.1(3) . . . . ?
C12 C6 C7 C8 28.6(3) . . . . ?
C15 C5 C6 C7 36.4(3) . . . . ?
C15 C5 C6 C12 150.5(2) . . . . ?
C16 O4 C2 O1 -48.3(3) . . . . ?
C16 O4 C2 C1 -162.7(2) . . . . ?
C16 O4 C2 C9 73.7(3) . . . . ?
C16 C4 C5 O2 162.8(2) . . . . ?
C16 C4 C5 C6 -86.3(3) . . . . ?
C16 C4 C5 C15 45.8(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_1_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc2j0kpt
_database_code_depnum_ccdc_archive 'CCDC 2324246'
loop_
_audit_author_name
_audit_author_address
'xiaoliang xu'
;yunnan university
China
;
_audit_update_record             
;
2024-01-09 deposited with the CCDC.	2024-02-26 downloaded from the CCDC.
;
_audit_creation_date             2024-01-09
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2024,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_diffrn_source_power             0.05500000000000001
_chemical_name_common            ?
_chemical_formula_sum            'C14 H18 O5'
_chemical_formula_moiety         'C14 H18 O5'
_chemical_formula_weight         266.28
_chemical_melting_point          ?
_exptl_crystal_colour_primary    colourless
_chemical_absolute_configuration ad
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C7(H7), C6(H6), C11(H11), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C3(H3A,H3B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.83220(10)
_cell_length_b                   6.90300(10)
_cell_length_c                   13.3006(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.2910(10)
_cell_angle_gamma                90
_cell_volume                     696.85(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298.00
_cell_measurement_reflns_used    9874
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      77.60
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6457
_exptl_absorpt_correction_T_max  0.7541
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0933 before and 0.0522 after correction.
The Ratio of minimum to maximum transmission is 0.8563.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.831
_shelx_estimated_absorpt_T_max   0.856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      298.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.1
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            19174
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_theta_min         3.429
_diffrn_reflns_theta_max         77.587
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2907
_reflns_number_gt                2858
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_max     0.963
_reflns_Friedel_fraction_full    0.988
_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.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0726P)²+0.0251P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2907
_refine_ls_number_parameters     176
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_Flack   0.09(3)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1258 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'

_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_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O -0.01268(14) 0.2896(2) 0.36270(10) 0.0610(3) Uani 1 1 d . . . . .
O3 O 0.59026(16) 0.2036(3) 0.48065(13) 0.0744(4) Uani 1 1 d . . . . .
H3 H 0.689981 0.241326 0.481764 0.112 Uiso 1 1 calc R U . . .
O1 O -0.05875(18) 0.2990(3) 0.52018(12) 0.0800(5) Uani 1 1 d . . . . .
O4 O 0.4438(2) 0.5549(3) 0.21236(13) 0.0857(5) Uani 1 1 d . . . . .
O5 O 0.1971(4) 0.5692(4) 0.00935(15) 0.1137(8) Uani 1 1 d . . . . .
C8 C 0.28912(19) 0.2069(2) 0.39862(14) 0.0539(4) Uani 1 1 d . . . . .
H8 H 0.292237 0.065340 0.393753 0.065 Uiso 1 1 calc R U . . .
C7 C 0.13332(19) 0.2826(3) 0.31281(13) 0.0511(3) Uani 1 1 d . . . . .
H7 H 0.106173 0.188708 0.255804 0.061 Uiso 1 1 calc R U . . .
C9 C 0.2390(2) 0.2608(3) 0.49863(14) 0.0590(4) Uani 1 1 d . . . . .
H9A H 0.271816 0.158873 0.550000 0.071 Uiso 1 1 calc R U . . .
H9B H 0.295845 0.380355 0.527204 0.071 Uiso 1 1 calc R U . . .
C6 C 0.1590(2) 0.4825(2) 0.26957(13) 0.0536(4) Uani 1 1 d . . . . .
H6 H 0.215652 0.569045 0.326462 0.064 Uiso 1 1 calc R U . . .
C10 C 0.0434(2) 0.2847(3) 0.46639(15) 0.0585(4) Uani 1 1 d . . . . .
C11 C 0.4680(2) 0.2860(3) 0.39351(15) 0.0587(4) Uani 1 1 d . . . . .
H11 H 0.468390 0.427390 0.400311 0.070 Uiso 1 1 calc R U . . .
C5 C 0.2720(3) 0.4703(3) 0.18999(14) 0.0646(5) Uani 1 1 d . . . . .
C2 C -0.0173(3) 0.5735(3) 0.20748(15) 0.0691(5) Uani 1 1 d . . . . .
H2 H -0.116437 0.525056 0.232966 0.083 Uiso 1 1 calc R U . . .
C13 C 0.4324(3) 0.3497(4) 0.19717(18) 0.0771(6) Uani 1 1 d . . . . .
C12 C 0.5136(2) 0.2305(4) 0.29234(18) 0.0771(6) Uani 1 1 d . . . . .
H12A H 0.640654 0.236759 0.303563 0.093 Uiso 1 1 calc R U . . .
H12B H 0.479265 0.096525 0.277310 0.093 Uiso 1 1 calc R U . . .
C4 C 0.1503(4) 0.5195(4) 0.08494(16) 0.0786(6) Uani 1 1 d . . . . .
C3 C -0.0325(4) 0.5068(4) 0.09587(16) 0.0812(6) Uani 1 1 d . . . . .
H3A H -0.076332 0.374990 0.085570 0.097 Uiso 1 1 calc R U . . .
H3B H -0.110161 0.591096 0.046652 0.097 Uiso 1 1 calc R U . . .
C1 C -0.0078(6) 0.7948(4) 0.2137(2) 0.1040(11) Uani 1 1 d . . . . .
H1A H 0.013248 0.834560 0.284918 0.156 Uiso 1 1 calc R U . . .
H1B H -0.117215 0.848762 0.174875 0.156 Uiso 1 1 calc R U . . .
H1C H 0.086442 0.839830 0.185375 0.156 Uiso 1 1 calc R U . . .
C14 C 0.4799(4) 0.2739(8) 0.1009(2) 0.1154(12) Uani 1 1 d . . . . .
H14A H 0.435731 0.360823 0.044118 0.173 Uiso 1 1 calc R U . . .
H14B H 0.428554 0.148069 0.084098 0.173 Uiso 1 1 calc R U . . .
H14C H 0.605738 0.264584 0.113393 0.173 Uiso 1 1 calc R U . . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C7 1.4577(19) . ?
O2 C10 1.341(2) . ?
O3 H3 0.8200 . ?
O3 C11 1.427(2) . ?
O1 C10 1.202(2) . ?
O4 C5 1.429(2) . ?
O4 C13 1.431(3) . ?
O5 C4 1.202(3) . ?
C8 H8 0.9800 . ?
C8 C7 1.542(2) . ?
C8 C9 1.523(3) . ?
C8 C11 1.520(2) . ?
C7 H7 0.9800 . ?
C7 C6 1.527(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.494(2) . ?
C6 H6 0.9800 . ?
C6 C5 1.540(3) . ?
C6 C2 1.556(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.524(3) . ?
C5 C13 1.490(4) . ?
C5 C4 1.523(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.531(3) . ?
C2 C1 1.530(4) . ?
C13 C12 1.512(4) . ?
C13 C14 1.512(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C4 C3 1.477(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 C7 111.88(12) . . ?
C11 O3 H3 109.5 . . ?
C5 O4 C13 62.81(15) . . ?
C7 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
C9 C8 C7 103.65(12) . . ?
C11 C8 H8 108.5 . . ?
C11 C8 C7 114.51(13) . . ?
C11 C8 C9 112.98(15) . . ?
O2 C7 C8 103.94(12) . . ?
O2 C7 H7 109.2 . . ?
O2 C7 C6 109.41(14) . . ?
C8 C7 H7 109.2 . . ?
C6 C7 C8 115.53(13) . . ?
C6 C7 H7 109.2 . . ?
C8 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
H9A C9 H9B 109.0 . . ?
C10 C9 C8 104.09(14) . . ?
C10 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
C7 C6 H6 109.7 . . ?
C7 C6 C5 111.15(14) . . ?
C7 C6 C2 112.50(15) . . ?
C5 C6 H6 109.7 . . ?
C5 C6 C2 104.03(15) . . ?
C2 C6 H6 109.7 . . ?
O2 C10 C9 110.52(14) . . ?
O1 C10 O2 120.86(14) . . ?
O1 C10 C9 128.62(16) . . ?
O3 C11 C8 105.16(14) . . ?
O3 C11 H11 109.6 . . ?
O3 C11 C12 111.11(16) . . ?
C8 C11 H11 109.6 . . ?
C8 C11 C12 111.63(16) . . ?
C12 C11 H11 109.6 . . ?
O4 C5 C6 120.37(15) . . ?
O4 C5 C13 58.64(16) . . ?
O4 C5 C4 116.35(16) . . ?
C13 C5 C6 127.19(17) . . ?
C13 C5 C4 120.67(19) . . ?
C4 C5 C6 106.42(18) . . ?
C6 C2 H2 110.7 . . ?
C3 C2 C6 103.87(17) . . ?
C3 C2 H2 110.7 . . ?
C1 C2 C6 110.5(2) . . ?
C1 C2 H2 110.7 . . ?
C1 C2 C3 110.2(2) . . ?
O4 C13 C5 58.55(15) . . ?
O4 C13 C12 114.9(2) . . ?
O4 C13 C14 116.2(3) . . ?
C5 C13 C12 122.11(17) . . ?
C5 C13 C14 121.3(2) . . ?
C12 C13 C14 112.3(3) . . ?
C11 C12 H12A 107.9 . . ?
C11 C12 H12B 107.9 . . ?
C13 C12 C11 117.41(19) . . ?
C13 C12 H12A 107.9 . . ?
C13 C12 H12B 107.9 . . ?
H12A C12 H12B 107.2 . . ?
O5 C4 C5 125.5(3) . . ?
O5 C4 C3 127.0(3) . . ?
C3 C4 C5 107.39(18) . . ?
C2 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C4 C3 C2 103.42(18) . . ?
C4 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
H3A C3 H3B 109.0 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
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 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C7 C6 C5 -163.39(13) . . . . ?
O2 C7 C6 C2 -47.19(18) . . . . ?
O3 C11 C12 C13 -162.64(18) . . . . ?
O4 C5 C13 C12 101.5(2) . . . . ?
O4 C5 C13 C14 -103.6(3) . . . . ?
O4 C5 C4 O5 24.2(4) . . . . ?
O4 C5 C4 C3 -152.3(2) . . . . ?
O4 C13 C12 C11 47.1(3) . . . . ?
O5 C4 C3 C2 -142.8(3) . . . . ?
C8 C7 C6 C5 79.78(18) . . . . ?
C8 C7 C6 C2 -164.02(15) . . . . ?
C8 C9 C10 O2 -12.2(2) . . . . ?
C8 C9 C10 O1 167.9(2) . . . . ?
C8 C11 C12 C13 80.3(2) . . . . ?
C7 O2 C10 O1 176.3(2) . . . . ?
C7 O2 C10 C9 -3.6(2) . . . . ?
C7 C8 C9 C10 21.75(18) . . . . ?
C7 C8 C11 O3 178.09(16) . . . . ?
C7 C8 C11 C12 -61.3(2) . . . . ?
C7 C6 C5 O4 -112.9(2) . . . . ?
C7 C6 C5 C13 -41.1(3) . . . . ?
C7 C6 C5 C4 111.92(17) . . . . ?
C7 C6 C2 C3 -91.0(2) . . . . ?
C7 C6 C2 C1 150.9(2) . . . . ?
C9 C8 C7 O2 -23.78(17) . . . . ?
C9 C8 C7 C6 96.08(16) . . . . ?
C9 C8 C11 O3 59.7(2) . . . . ?
C9 C8 C11 C12 -179.69(18) . . . . ?
C6 C5 C13 O4 -106.3(2) . . . . ?
C6 C5 C13 C12 -4.8(3) . . . . ?
C6 C5 C13 C14 150.1(3) . . . . ?
C6 C5 C4 O5 161.4(3) . . . . ?
C6 C5 C4 C3 -15.0(2) . . . . ?
C6 C2 C3 C4 -39.0(2) . . . . ?
C10 O2 C7 C8 17.6(2) . . . . ?
C10 O2 C7 C6 -106.34(17) . . . . ?
C11 C8 C7 O2 -147.31(16) . . . . ?
C11 C8 C7 C6 -27.4(2) . . . . ?
C11 C8 C9 C10 146.27(16) . . . . ?
C5 O4 C13 C12 -113.74(19) . . . . ?
C5 O4 C13 C14 112.1(3) . . . . ?
C5 C6 C2 C3 29.4(2) . . . . ?
C5 C6 C2 C1 -88.7(2) . . . . ?
C5 C13 C12 C11 -20.1(3) . . . . ?
C5 C4 C3 C2 33.6(2) . . . . ?
C2 C6 C5 O4 125.8(2) . . . . ?
C2 C6 C5 C13 -162.4(2) . . . . ?
C2 C6 C5 C4 -9.4(2) . . . . ?
C13 O4 C5 C6 117.6(2) . . . . ?
C13 O4 C5 C4 -111.4(2) . . . . ?
C13 C5 C4 O5 -43.4(4) . . . . ?
C13 C5 C4 C3 140.2(2) . . . . ?
C4 C5 C13 O4 104.1(2) . . . . ?
C4 C5 C13 C12 -154.4(2) . . . . ?
C4 C5 C13 C14 0.5(4) . . . . ?
C1 C2 C3 C4 79.3(3) . . . . ?
C14 C13 C12 C11 -177.0(2) . . . . ?

####################################################################### 
# 
# 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_1_CCDC2
_audit_block_doi                 10.5517/ccdc.csd.cc2j0kqv
_database_code_depnum_ccdc_archive 'CCDC 2324247'
loop_
_audit_author_name
_audit_author_address
'xiaoliang xu'
;yunnan university
China
;
_audit_update_record             
;
2024-01-09 deposited with the CCDC.	2024-02-26 downloaded from the CCDC.
;
_audit_creation_date             2024-01-08
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2024,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_diffrn_source_power             0.05500000000000001
_chemical_name_common            ?
_chemical_formula_sum            'C15 H20 O5'
_chemical_formula_moiety         'C15 H18 O4, H2 O'
_chemical_formula_weight         280.31
_chemical_melting_point          ?
_exptl_crystal_colour_primary    colourless
_chemical_absolute_configuration ad
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Ternary CH refined with riding coordinates:
 C7(H7), C12(H12), C9(H9), C8(H8), C6(H6)
2.c Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.e Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C1(H1A,H1B,H1C)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5642(3)
_cell_length_b                   7.7285(2)
_cell_length_c                   10.2740(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.7530(10)
_cell_angle_gamma                90
_cell_volume                     737.65(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298.00
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      7.24
_cell_measurement_theta_max      77.77
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5877
_exptl_absorpt_correction_T_max  0.7541
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1180 before and 0.0529 after correction.
The Ratio of minimum to maximum transmission is 0.7793.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.835
_shelx_estimated_absorpt_T_max   0.905
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      298.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.1
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            19587
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_theta_min         7.244
_diffrn_reflns_theta_max         77.763
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             3028
_reflns_number_gt                2986
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_max     0.922
_reflns_Friedel_fraction_full    0.955
_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.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0675P)²+0.0773P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3028
_refine_ls_number_parameters     188
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   -0.05(10)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1298 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'

_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_
_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 0.54224(18) 0.4157(3) 1.08062(14) 0.0630(5) Uani 1 1 d . . . . .
H4 H 0.463126 0.445782 1.090358 0.094 Uiso 1 1 calc R U . . .
O2 O 0.83757(17) 0.5861(3) 0.79898(16) 0.0694(6) Uani 1 1 d . . . . .
O5 O 0.28910(18) 0.5165(3) 0.14631(16) 0.0657(5) Uani 1 1 d G . . . .
H5A H 0.286903 0.500474 0.227653 0.098 Uiso 1 1 d G U . . .
H5B H 0.207189 0.501178 0.093174 0.098 Uiso 1 1 d G U . . .
O1 O 0.30350(19) 0.4479(4) 0.40998(16) 0.0830(7) Uani 1 1 d . . . . .
O3 O 1.04192(18) 0.5199(5) 0.9402(2) 0.0983(9) Uani 1 1 d . . . . .
C7 C 0.6837(2) 0.5686(3) 0.78495(19) 0.0472(4) Uani 1 1 d . . . . .
H7 H 0.637243 0.678963 0.753673 0.057 Uiso 1 1 calc R U . . .
C12 C 0.5422(2) 0.4207(3) 0.94103(17) 0.0458(4) Uani 1 1 d . . . . .
H12 H 0.558922 0.303361 0.911810 0.055 Uiso 1 1 calc R U . . .
C5 C 0.4583(2) 0.4441(3) 0.63542(18) 0.0469(4) Uani 1 1 d . . . . .
C9 C 0.8144(2) 0.4593(3) 0.99999(19) 0.0527(5) Uani 1 1 d . . . . .
H9 H 0.808284 0.332915 0.993330 0.063 Uiso 1 1 calc R U . . .
C8 C 0.6679(2) 0.5348(3) 0.92855(18) 0.0429(4) Uani 1 1 d . . . . .
H8 H 0.656929 0.646781 0.969732 0.052 Uiso 1 1 calc R U . . .
C10 C 0.9124(2) 0.5217(4) 0.9148(2) 0.0633(6) Uani 1 1 d . . . . .
C13 C 0.3967(2) 0.4830(3) 0.86006(19) 0.0521(5) Uani 1 1 d . . . . .
H13A H 0.323184 0.420118 0.891369 0.063 Uiso 1 1 calc R U . . .
H13B H 0.387379 0.603882 0.881832 0.063 Uiso 1 1 calc R U . . .
C6 C 0.6212(2) 0.4276(3) 0.68282(18) 0.0461(4) Uani 1 1 d . . . . .
H6 H 0.645332 0.313654 0.723803 0.055 Uiso 1 1 calc R U . . .
C14 C 0.3620(2) 0.4679(3) 0.7099(2) 0.0508(5) Uani 1 1 d . . . . .
C4 C 0.4235(2) 0.4473(4) 0.48680(19) 0.0567(5) Uani 1 1 d . . . . .
C2 C 0.6698(2) 0.4370(5) 0.5519(2) 0.0614(6) Uani 1 1 d . . . . .
C3 C 0.5589(3) 0.4469(5) 0.4464(2) 0.0657(6) Uani 1 1 d . . . . .
H3 H 0.566930 0.452824 0.358069 0.079 Uiso 1 1 calc R U . . .
C11 C 0.8724(3) 0.5069(7) 1.1456(2) 0.0942(13) Uani 1 1 d . . . . .
H11A H 0.881319 0.630359 1.153907 0.141 Uiso 1 1 calc R U . . .
H11B H 0.965096 0.454446 1.178197 0.141 Uiso 1 1 calc R U . . .
H11C H 0.807528 0.466080 1.197235 0.141 Uiso 1 1 calc R U . . .
C15 C 0.2030(3) 0.4871(6) 0.6504(3) 0.0809(10) Uani 1 1 d . . . . .
H15A H 0.187859 0.540084 0.563693 0.121 Uiso 1 1 calc R U . . .
H15B H 0.161382 0.558297 0.707906 0.121 Uiso 1 1 calc R U . . .
H15C H 0.158301 0.375089 0.641790 0.121 Uiso 1 1 calc R U . . .
C1 C 0.8241(3) 0.4253(9) 0.5459(3) 0.1060(15) Uani 1 1 d . . . . .
H1A H 0.871203 0.533502 0.573593 0.159 Uiso 1 1 calc R U . . .
H1B H 0.829637 0.400166 0.455721 0.159 Uiso 1 1 calc R U . . .
H1C H 0.870680 0.334875 0.604422 0.159 Uiso 1 1 calc R U . . .


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 H4 0.8200 . ?
O4 C12 1.435(2) . ?
O2 C7 1.450(2) . ?
O2 C10 1.331(3) . ?
O5 H5A 0.8501 . ?
O5 H5B 0.8500 . ?
O1 C4 1.229(3) . ?
O3 C10 1.203(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.541(3) . ?
C7 C6 1.532(3) . ?
C12 H12 0.9800 . ?
C12 C8 1.521(3) . ?
C12 C13 1.520(3) . ?
C5 C6 1.523(3) . ?
C5 C14 1.343(3) . ?
C5 C4 1.484(2) . ?
C9 H9 0.9800 . ?
C9 C8 1.534(3) . ?
C9 C10 1.506(3) . ?
C9 C11 1.512(3) . ?
C8 H8 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.504(3) . ?
C6 H6 0.9800 . ?
C6 C2 1.526(3) . ?
C14 C15 1.506(3) . ?
C4 C3 1.451(3) . ?
C2 C3 1.326(3) . ?
C2 C1 1.495(3) . ?
C3 H3 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C12 O4 H4 109.5 . . ?
C10 O2 C7 111.79(17) . . ?
H5A O5 H5B 112.1 . . ?
O2 C7 H7 108.8 . . ?
O2 C7 C8 104.43(15) . . ?
O2 C7 C6 110.87(17) . . ?
C8 C7 H7 108.8 . . ?
C6 C7 H7 108.8 . . ?
C6 C7 C8 115.08(17) . . ?
O4 C12 H12 108.7 . . ?
O4 C12 C8 106.69(16) . . ?
O4 C12 C13 109.78(17) . . ?
C8 C12 H12 108.7 . . ?
C13 C12 H12 108.7 . . ?
C13 C12 C8 114.17(18) . . ?
C14 C5 C6 128.12(17) . . ?
C14 C5 C4 124.60(19) . . ?
C4 C5 C6 107.01(16) . . ?
C8 C9 H9 108.3 . . ?
C10 C9 H9 108.3 . . ?
C10 C9 C8 102.98(18) . . ?
C10 C9 C11 111.4(2) . . ?
C11 C9 H9 108.3 . . ?
C11 C9 C8 117.3(2) . . ?
C7 C8 H8 108.0 . . ?
C12 C8 C7 116.03(15) . . ?
C12 C8 C9 112.93(17) . . ?
C12 C8 H8 108.0 . . ?
C9 C8 C7 103.65(15) . . ?
C9 C8 H8 108.0 . . ?
O2 C10 C9 111.24(18) . . ?
O3 C10 O2 120.4(2) . . ?
O3 C10 C9 128.4(2) . . ?
C12 C13 H13A 107.5 . . ?
C12 C13 H13B 107.5 . . ?
H13A C13 H13B 107.0 . . ?
C14 C13 C12 119.14(17) . . ?
C14 C13 H13A 107.5 . . ?
C14 C13 H13B 107.5 . . ?
C7 C6 H6 109.3 . . ?
C5 C6 C7 111.27(17) . . ?
C5 C6 H6 109.3 . . ?
C5 C6 C2 102.54(16) . . ?
C2 C6 C7 114.76(19) . . ?
C2 C6 H6 109.3 . . ?
C5 C14 C13 125.57(18) . . ?
C5 C14 C15 123.10(19) . . ?
C13 C14 C15 111.33(18) . . ?
O1 C4 C5 127.4(2) . . ?
O1 C4 C3 125.3(2) . . ?
C3 C4 C5 107.30(18) . . ?
C3 C2 C6 111.78(19) . . ?
C3 C2 C1 125.1(2) . . ?
C1 C2 C6 123.0(2) . . ?
C4 C3 H3 124.4 . . ?
C2 C3 C4 111.18(19) . . ?
C2 C3 H3 124.4 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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
O4 C12 C8 C7 -176.31(18) . . . . ?
O4 C12 C8 C9 64.2(2) . . . . ?
O4 C12 C13 C14 -169.0(2) . . . . ?
O2 C7 C8 C12 -148.27(18) . . . . ?
O2 C7 C8 C9 -23.9(2) . . . . ?
O2 C7 C6 C5 -162.67(17) . . . . ?
O2 C7 C6 C2 -46.8(3) . . . . ?
O1 C4 C3 C2 -176.7(3) . . . . ?
C7 O2 C10 O3 177.2(3) . . . . ?
C7 O2 C10 C9 -3.4(3) . . . . ?
C7 C6 C2 C3 -123.8(3) . . . . ?
C7 C6 C2 C1 59.6(5) . . . . ?
C12 C13 C14 C5 -17.5(4) . . . . ?
C12 C13 C14 C15 163.8(2) . . . . ?
C5 C6 C2 C3 -3.0(3) . . . . ?
C5 C6 C2 C1 -179.6(4) . . . . ?
C5 C4 C3 C2 2.4(4) . . . . ?
C8 C7 C6 C5 79.1(2) . . . . ?
C8 C7 C6 C2 -165.03(19) . . . . ?
C8 C12 C13 C14 71.3(3) . . . . ?
C8 C9 C10 O2 -12.3(3) . . . . ?
C8 C9 C10 O3 167.1(3) . . . . ?
C10 O2 C7 C8 17.5(3) . . . . ?
C10 O2 C7 C6 -107.0(2) . . . . ?
C10 C9 C8 C7 21.6(2) . . . . ?
C10 C9 C8 C12 147.99(19) . . . . ?
C13 C12 C8 C7 -54.9(2) . . . . ?
C13 C12 C8 C9 -174.33(17) . . . . ?
C6 C7 C8 C12 -26.5(2) . . . . ?
C6 C7 C8 C9 97.9(2) . . . . ?
C6 C5 C14 C13 -0.3(4) . . . . ?
C6 C5 C14 C15 178.3(3) . . . . ?
C6 C5 C4 O1 174.8(3) . . . . ?
C6 C5 C4 C3 -4.3(3) . . . . ?
C6 C2 C3 C4 0.5(4) . . . . ?
C14 C5 C6 C7 -46.7(3) . . . . ?
C14 C5 C6 C2 -169.9(3) . . . . ?
C14 C5 C4 O1 -10.7(5) . . . . ?
C14 C5 C4 C3 170.2(3) . . . . ?
C4 C5 C6 C7 127.5(2) . . . . ?
C4 C5 C6 C2 4.3(3) . . . . ?
C4 C5 C14 C13 -173.5(2) . . . . ?
C4 C5 C14 C15 5.1(4) . . . . ?
C11 C9 C8 C7 144.3(3) . . . . ?
C11 C9 C8 C12 -89.3(3) . . . . ?
C11 C9 C10 O2 -138.9(3) . . . . ?
C11 C9 C10 O3 40.5(5) . . . . ?
C1 C2 C3 C4 177.0(4) . . . . ?

####################################################################### 
# 
# 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_1_CCDC3
_audit_block_doi                 10.5517/ccdc.csd.cc2hyk23
_database_code_depnum_ccdc_archive 'CCDC 2322305'
loop_
_audit_author_name
_audit_author_address
'xiaoliang xu'
;yunnan university
China
;
_audit_update_record             
;
2023-12-28 deposited with the CCDC.	2024-02-26 downloaded from the CCDC.
;
_audit_creation_date             2022-05-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H22 O6'
_chemical_formula_sum            'C18 H22 O6'
_chemical_formula_weight         334.35
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.3182(12)
_cell_length_b                   11.8250(19)
_cell_length_c                   19.235(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1664.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9550
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.18
_cell_measurement_theta_min      4.60
_shelx_estimated_absorpt_T_max   0.760
_shelx_estimated_absorpt_T_min   0.722
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6807
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1276 before and 0.0732 after correction.
The Ratio of minimum to maximum transmission is 0.9039.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22371
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.178
_diffrn_reflns_theta_min         4.597
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3001
_reflns_number_total             3023
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1239 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3023
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0272
_refine_ls_restrained_S_all      1.024
_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)+(0.0464P)²+0.2874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0733
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C17(H17A,H17B)
2.c Tetrahedral OH refined with riding coordinates:
 O3(H3)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.67730(15) 0.50504(10) 0.51542(6) 0.0224(3) Uani 1 1 d . . . . .
O2 O 0.41715(17) 0.47688(11) 0.44637(6) 0.0272(3) Uani 1 1 d . . . . .
O3 O 0.11485(17) 0.31013(11) 0.74770(7) 0.0289(3) Uani 1 1 d . . . . .
H3 H 0.074075 0.279282 0.783847 0.043 Uiso 1 1 calc R U . . .
O4 O 1.0114(2) 0.64656(11) 0.64198(8) 0.0362(3) Uani 1 1 d . . . . .
O5 O 0.78399(17) 0.55646(10) 0.69459(7) 0.0272(3) Uani 1 1 d . . . . .
O6 O 0.19911(19) 0.35790(13) 0.47612(7) 0.0359(3) Uani 1 1 d . . . . .
C1 C 0.6504(3) 0.59899(16) 0.40791(10) 0.0313(4) Uani 1 1 d . . . . .
H1A H 0.712362 0.534682 0.386074 0.047 Uiso 1 1 calc R U . . .
H1B H 0.741232 0.655153 0.422355 0.047 Uiso 1 1 calc R U . . .
H1C H 0.565801 0.633351 0.374527 0.047 Uiso 1 1 calc R U . . .
C2 C 0.5453(2) 0.55863(15) 0.47066(9) 0.0241(4) Uani 1 1 d . . . . .
C3 C 0.6085(2) 0.43247(13) 0.56296(8) 0.0192(3) Uani 1 1 d . . . . .
C4 C 0.7440(2) 0.40005(13) 0.61857(9) 0.0216(3) Uani 1 1 d . . . . .
H4 H 0.754088 0.315810 0.621081 0.026 Uiso 1 1 calc R U . . .
C5 C 0.6907(2) 0.44717(14) 0.69034(9) 0.0213(3) Uani 1 1 d . . . . .
H5 H 0.738386 0.395871 0.727481 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4871(2) 0.46650(13) 0.70135(8) 0.0197(3) Uani 1 1 d . . . . .
H6 H 0.444810 0.530753 0.671626 0.024 Uiso 1 1 calc R U . . .
C7 C 0.4377(2) 0.48993(15) 0.77813(9) 0.0249(4) Uani 1 1 d . . . . .
H7 H 0.544932 0.523828 0.802706 0.030 Uiso 1 1 calc R U . . .
C8 C 0.3998(3) 0.37042(16) 0.80671(9) 0.0288(4) Uani 1 1 d . . . . .
H8A H 0.515176 0.333922 0.821520 0.035 Uiso 1 1 calc R U . . .
H8B H 0.316451 0.374280 0.847173 0.035 Uiso 1 1 calc R U . . .
C9 C 0.4485(3) 0.65299(16) 0.50953(11) 0.0334(4) Uani 1 1 d . . . . .
H9A H 0.365256 0.692433 0.477826 0.050 Uiso 1 1 calc R U . . .
H9B H 0.539085 0.706519 0.527557 0.050 Uiso 1 1 calc R U . . .
H9C H 0.378688 0.620928 0.548279 0.050 Uiso 1 1 calc R U . . .
C10 C 0.3373(2) 0.40569(15) 0.49369(9) 0.0243(4) Uani 1 1 d . . . . .
C11 C 0.4372(2) 0.38950(14) 0.55882(9) 0.0204(3) Uani 1 1 d . . . . .
C12 C 0.3607(2) 0.32177(14) 0.61697(9) 0.0209(3) Uani 1 1 d . . . . .
C13 C 0.2622(3) 0.21314(14) 0.60044(10) 0.0287(4) Uani 1 1 d . . . . .
H13A H 0.228890 0.174852 0.643815 0.043 Uiso 1 1 calc R U . . .
H13B H 0.342321 0.163965 0.573000 0.043 Uiso 1 1 calc R U . . .
H13C H 0.151403 0.229945 0.573774 0.043 Uiso 1 1 calc R U . . .
C14 C 0.3834(2) 0.35952(14) 0.68203(9) 0.0208(3) Uani 1 1 d . . . . .
C15 C 0.3115(2) 0.30351(15) 0.74750(9) 0.0250(4) Uani 1 1 d . . . . .
H15 H 0.351589 0.222714 0.749317 0.030 Uiso 1 1 calc R U . . .
C16 C 0.2730(3) 0.56837(17) 0.78422(10) 0.0325(4) Uani 1 1 d . . . . .
H16A H 0.298663 0.639406 0.759850 0.049 Uiso 1 1 calc R U . . .
H16B H 0.248687 0.584122 0.833371 0.049 Uiso 1 1 calc R U . . .
H16C H 0.165957 0.531991 0.763341 0.049 Uiso 1 1 calc R U . . .
C17 C 0.9335(2) 0.45154(15) 0.60891(10) 0.0251(4) Uani 1 1 d . . . . .
H17A H 1.029139 0.402398 0.629214 0.030 Uiso 1 1 calc R U . . .
H17B H 0.960744 0.464001 0.559086 0.030 Uiso 1 1 calc R U . . .
C18 C 0.9204(2) 0.56178(15) 0.64735(9) 0.0262(4) 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
O1 C2 1.441(2) . ?
O1 C3 1.351(2) . ?
O2 C2 1.426(2) . ?
O2 C10 1.371(2) . ?
O3 H3 0.8400 . ?
O3 C15 1.442(2) . ?
O4 C18 1.208(2) . ?
O5 C5 1.4638(19) . ?
O5 C18 1.352(2) . ?
O6 C10 1.207(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.509(3) . ?
C2 C9 1.518(2) . ?
C3 C4 1.508(2) . ?
C3 C11 1.355(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.539(2) . ?
C4 C17 1.526(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.522(2) . ?
C6 H6 1.0000 . ?
C6 C7 1.545(2) . ?
C6 C14 1.521(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.542(2) . ?
C7 C16 1.525(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C15 1.530(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.463(2) . ?
C11 C12 1.485(2) . ?
C12 C13 1.507(2) . ?
C12 C14 1.339(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.517(2) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.502(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
C3 O1 C2 115.71(13) . . ?
C10 O2 C2 118.64(13) . . ?
C15 O3 H3 109.5 . . ?
C18 O5 C5 110.36(13) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 105.99(14) . . ?
O1 C2 C9 109.98(14) . . ?
O2 C2 O1 109.79(13) . . ?
O2 C2 C1 106.72(14) . . ?
O2 C2 C9 110.67(15) . . ?
C1 C2 C9 113.53(16) . . ?
O1 C3 C4 113.36(14) . . ?
O1 C3 C11 122.90(15) . . ?
C11 C3 C4 123.68(15) . . ?
C3 C4 H4 109.6 . . ?
C3 C4 C5 112.20(13) . . ?
C3 C4 C17 114.18(14) . . ?
C5 C4 H4 109.6 . . ?
C17 C4 H4 109.6 . . ?
C17 C4 C5 101.24(13) . . ?
O5 C5 C4 104.58(13) . . ?
O5 C5 H5 109.5 . . ?
O5 C5 C6 108.42(13) . . ?
C4 C5 H5 109.5 . . ?
C6 C5 C4 115.28(13) . . ?
C6 C5 H5 109.5 . . ?
C5 C6 H6 109.7 . . ?
C5 C6 C7 112.89(14) . . ?
C7 C6 H6 109.7 . . ?
C14 C6 C5 109.23(13) . . ?
C14 C6 H6 109.7 . . ?
C14 C6 C7 105.41(13) . . ?
C6 C7 H7 109.9 . . ?
C8 C7 C6 102.62(13) . . ?
C8 C7 H7 109.9 . . ?
C16 C7 C6 111.55(14) . . ?
C16 C7 H7 109.9 . . ?
C16 C7 C8 112.83(15) . . ?
C7 C8 H8A 110.4 . . ?
C7 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
C15 C8 C7 106.53(13) . . ?
C15 C8 H8A 110.4 . . ?
C15 C8 H8B 110.4 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 C11 115.85(15) . . ?
O6 C10 O2 117.32(16) . . ?
O6 C10 C11 126.67(17) . . ?
C3 C11 C10 117.61(15) . . ?
C3 C11 C12 120.45(15) . . ?
C10 C11 C12 121.80(15) . . ?
C11 C12 C13 118.77(15) . . ?
C14 C12 C11 118.50(15) . . ?
C14 C12 C13 122.73(16) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C6 124.58(15) . . ?
C12 C14 C15 125.96(15) . . ?
C15 C14 C6 109.46(14) . . ?
O3 C15 C8 113.06(16) . . ?
O3 C15 C14 108.95(14) . . ?
O3 C15 H15 110.1 . . ?
C8 C15 H15 110.1 . . ?
C14 C15 C8 104.23(14) . . ?
C14 C15 H15 110.1 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C17 H17A 111.1 . . ?
C4 C17 H17B 111.1 . . ?
H17A C17 H17B 109.1 . . ?
C18 C17 C4 103.22(14) . . ?
C18 C17 H17A 111.1 . . ?
C18 C17 H17B 111.1 . . ?
O4 C18 O5 120.22(17) . . ?
O4 C18 C17 130.04(17) . . ?
O5 C18 C17 109.73(15) . . ?

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
O3 H3 O4 0.84 2.21 3.0163(19) 160.5 3_646 yes
C1 H1C O4 0.98 2.65 3.318(2) 125.5 2_466 yes
C15 H15 O5 1.00 2.45 3.204(2) 131.5 3_646 yes
C17 H17A O3 0.99 2.60 3.418(2) 139.6 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
O1 C3 C4 C5 112.23(15) . . . . ?
O1 C3 C4 C17 -2.22(19) . . . . ?
O1 C3 C11 C10 11.9(2) . . . . ?
O1 C3 C11 C12 -172.25(14) . . . . ?
O2 C10 C11 C3 -8.9(2) . . . . ?
O2 C10 C11 C12 175.29(14) . . . . ?
O5 C5 C6 C7 -75.05(17) . . . . ?
O5 C5 C6 C14 168.03(13) . . . . ?
O6 C10 C11 C3 166.32(17) . . . . ?
O6 C10 C11 C12 -9.5(3) . . . . ?
C2 O1 C3 C4 -166.54(13) . . . . ?
C2 O1 C3 C11 16.3(2) . . . . ?
C2 O2 C10 O6 161.77(16) . . . . ?
C2 O2 C10 C11 -22.5(2) . . . . ?
C3 O1 C2 O2 -44.86(18) . . . . ?
C3 O1 C2 C1 -159.77(14) . . . . ?
C3 O1 C2 C9 77.14(18) . . . . ?
C3 C4 C5 O5 -91.70(15) . . . . ?
C3 C4 C5 C6 27.2(2) . . . . ?
C3 C4 C17 C18 89.55(17) . . . . ?
C3 C11 C12 C13 -134.61(16) . . . . ?
C3 C11 C12 C14 44.9(2) . . . . ?
C4 C3 C11 C10 -164.96(15) . . . . ?
C4 C3 C11 C12 10.9(2) . . . . ?
C4 C5 C6 C7 168.15(13) . . . . ?
C4 C5 C6 C14 51.23(19) . . . . ?
C4 C17 C18 O4 -158.90(19) . . . . ?
C4 C17 C18 O5 22.09(18) . . . . ?
C5 O5 C18 O4 178.59(17) . . . . ?
C5 O5 C18 C17 -2.30(18) . . . . ?
C5 C4 C17 C18 -31.21(16) . . . . ?
C5 C6 C7 C8 -90.19(17) . . . . ?
C5 C6 C7 C16 148.75(15) . . . . ?
C5 C6 C14 C12 -71.6(2) . . . . ?
C5 C6 C14 C15 108.31(15) . . . . ?
C6 C7 C8 C15 -34.88(18) . . . . ?
C6 C14 C15 O3 112.69(15) . . . . ?
C6 C14 C15 C8 -8.26(18) . . . . ?
C7 C6 C14 C12 166.83(16) . . . . ?
C7 C6 C14 C15 -13.25(18) . . . . ?
C7 C8 C15 O3 -91.25(17) . . . . ?
C7 C8 C15 C14 26.92(18) . . . . ?
C10 O2 C2 O1 48.85(19) . . . . ?
C10 O2 C2 C1 163.29(15) . . . . ?
C10 O2 C2 C9 -72.74(19) . . . . ?
C10 C11 C12 C13 41.1(2) . . . . ?
C10 C11 C12 C14 -139.42(17) . . . . ?
C11 C3 C4 C5 -70.65(19) . . . . ?
C11 C3 C4 C17 174.90(15) . . . . ?
C11 C12 C14 C6 -1.6(2) . . . . ?
C11 C12 C14 C15 178.51(15) . . . . ?
C12 C14 C15 O3 -67.4(2) . . . . ?
C12 C14 C15 C8 171.66(17) . . . . ?
C13 C12 C14 C6 177.89(15) . . . . ?
C13 C12 C14 C15 -2.0(3) . . . . ?
C14 C6 C7 C8 28.97(17) . . . . ?
C14 C6 C7 C16 -92.10(16) . . . . ?
C16 C7 C8 C15 85.30(17) . . . . ?
C17 C4 C5 O5 30.45(15) . . . . ?
C17 C4 C5 C6 149.40(14) . . . . ?
C18 O5 C5 C4 -18.39(16) . . . . ?
C18 O5 C5 C6 -141.88(14) . . . . ?

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

data_1_CCDC4
_audit_block_doi                 10.5517/ccdc.csd.cc2hyhwv
_database_code_depnum_ccdc_archive 'CCDC 2322268'
loop_
_audit_author_name
_audit_author_address
'xiaoliang xu'
;YNU
China
;
_audit_update_record             
;
2023-12-28 deposited with the CCDC.	2024-02-26 downloaded from the CCDC.
;
_audit_creation_date             2023-07-07
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C14 H20 O4'
_diffrn_source_power             0.05500000000000001
_chemical_formula_moiety         'C14 H20 O4'
_chemical_formula_weight         252.30
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_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:
 C3(H3A), C4(H4A), C5(H5), C6(H6), C8(H8A), C12(H12), C17(H17), C18(H18),
 C19(H19), C20(H20), C23(H23), C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B), C11(H11A,H11B), C16(H16A,H16B), C22(H22A,H22B),
 C27(H27A,H27B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C26(H26A,H26B,
 H26C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O7(H7), O8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   9.3343(3)
_cell_length_b                   9.3343(3)
_cell_length_c                   26.7238(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2016.47(18)
_cell_formula_units_Z            6
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9810
_cell_measurement_theta_min      4.96
_cell_measurement_theta_max      77.38
_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6781
_exptl_absorpt_correction_T_max  0.7541
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1361 before and 0.0517 after correction.
The Ratio of minimum to maximum transmission is 0.8992.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.891
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.1
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            58155
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_theta_min         4.965
_diffrn_reflns_theta_max         77.371
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5704
_reflns_number_gt                5682
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.994
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.999
_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.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+0.3760P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5704
_refine_ls_number_parameters     333
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0773
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_abs_structure_details 
;
 Flack x determined using 2790 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'

_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_
_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 1.52031(19) 1.2087(3) 0.35851(7) 0.0557(6) Uani 1 1 d . . . . .
O2 O 1.24637(15) 1.05878(17) 0.34997(5) 0.0257(3) Uani 1 1 d . . . . .
O3 O 0.6496(2) 0.6955(2) 0.48055(6) 0.0534(6) Uani 1 1 d . . . . .
H3 H 0.705688 0.776170 0.499599 0.080 Uiso 1 1 calc R U . . .
O4 O 1.07796(18) 1.22719(15) 0.47102(5) 0.0276(3) Uani 1 1 d . . . . .
H4 H 1.168536 1.297767 0.483644 0.041 Uiso 1 1 calc R U . . .
C1 C 1.3860(2) 1.1915(3) 0.36747(7) 0.0360(5) Uani 1 1 d . . . . .
C2 C 1.3438(3) 1.3014(3) 0.39693(8) 0.0406(6) Uani 1 1 d . . . . .
H2A H 1.416353 1.418834 0.387635 0.049 Uiso 1 1 calc R U . . .
H2B H 1.354246 1.288563 0.433296 0.049 Uiso 1 1 calc R U . . .
C3 C 1.1653(3) 1.2422(2) 0.38268(7) 0.0261(4) Uani 1 1 d . . . . .
H3A H 1.167304 1.301480 0.351294 0.031 Uiso 1 1 calc R U . . .
C4 C 1.0993(2) 1.0600(2) 0.36875(6) 0.0177(3) Uani 1 1 d . . . . .
H4A H 1.017814 1.029466 0.340819 0.021 Uiso 1 1 calc R U . . .
C5 C 1.0188(2) 0.93679(19) 0.41123(6) 0.0167(3) Uani 1 1 d . . . . .
H5 H 1.085405 0.983436 0.442406 0.020 Uiso 1 1 calc R U . . .
C6 C 0.9979(3) 0.7647(2) 0.40100(8) 0.0324(5) Uani 1 1 d . . . . .
H6 H 0.964049 0.733550 0.365355 0.039 Uiso 1 1 calc R U . . .
C7 C 0.8530(4) 0.6526(3) 0.43527(10) 0.0500(7) Uani 1 1 d . . . . .
H7A H 0.797219 0.537056 0.423010 0.060 Uiso 1 1 calc R U . . .
H7B H 0.892561 0.654973 0.469805 0.060 Uiso 1 1 calc R U . . .
C8 C 0.7358(3) 0.7200(3) 0.43405(8) 0.0389(6) Uani 1 1 d . . . . .
H8A H 0.652935 0.662791 0.406829 0.047 Uiso 1 1 calc R U . . .
C9 C 0.8432(2) 0.9022(2) 0.42035(6) 0.0208(3) Uani 1 1 d . . . . .
C10 C 0.7837(2) 1.0053(3) 0.41698(6) 0.0297(4) Uani 1 1 d . . . . .
C11 C 0.8830(3) 1.1902(3) 0.40852(8) 0.0390(5) Uani 1 1 d . . . . .
H11A H 0.831941 1.242313 0.428453 0.047 Uiso 1 1 calc R U . . .
H11B H 0.872341 1.211715 0.372825 0.047 Uiso 1 1 calc R U . . .
C12 C 1.0656(3) 1.2762(2) 0.42123(7) 0.0311(4) Uani 1 1 d . . . . .
H12 H 1.108068 1.398070 0.421545 0.037 Uiso 1 1 calc R U . . .
C13 C 0.6013(3) 0.9443(5) 0.42409(9) 0.0583(9) Uani 1 1 d . . . . .
H13A H 0.537965 0.824617 0.418367 0.087 Uiso 1 1 calc R U . . .
H13B H 0.565928 1.000189 0.400232 0.087 Uiso 1 1 calc R U . . .
H13C H 0.581935 0.968575 0.458294 0.087 Uiso 1 1 calc R U . . .
C14 C 1.1515(5) 0.7526(4) 0.41156(11) 0.0617(9) Uani 1 1 d . . . . .
H14A H 1.240273 0.825751 0.388698 0.093 Uiso 1 1 calc R U . . .
H14B H 1.126226 0.638304 0.406606 0.093 Uiso 1 1 calc R U . . .
H14C H 1.187007 0.786071 0.446194 0.093 Uiso 1 1 calc R U . . .
O5 O 0.3972(2) 0.87640(18) 0.64155(6) 0.0397(4) Uani 1 1 d . . . . .
O6 O 0.24920(16) 0.60231(16) 0.65043(5) 0.0245(3) Uani 1 1 d . . . . .
O7 O 0.37834(16) 0.43859(16) 0.51935(5) 0.0255(3) Uani 1 1 d . . . . .
H7 H 0.454374 0.517944 0.503524 0.038 Uiso 1 1 calc R U . . .
O8 O -0.16348(17) -0.01554(16) 0.53252(5) 0.0282(3) Uani 1 1 d . . . . .
H8 H -0.103171 0.042549 0.508855 0.042 Uiso 1 1 calc R U . . .
C15 C 0.3753(3) 0.7423(2) 0.63060(7) 0.0302(4) Uani 1 1 d . . . . .
C16 C 0.4723(3) 0.6983(3) 0.59507(9) 0.0379(5) Uani 1 1 d . . . . .
H16A H 0.592767 0.772223 0.599804 0.045 Uiso 1 1 calc R U . . .
H16B H 0.443614 0.706036 0.559889 0.045 Uiso 1 1 calc R U . . .
C17 C 0.4210(2) 0.5211(2) 0.60873(7) 0.0266(4) Uani 1 1 d . . . . .
H17 H 0.492932 0.525465 0.637111 0.032 Uiso 1 1 calc R U . . .
C18 C 0.2456(2) 0.4550(2) 0.62975(6) 0.0191(3) Uani 1 1 d . . . . .
H18 H 0.227031 0.376036 0.657604 0.023 Uiso 1 1 calc R U . . .
C19 C 0.10723(19) 0.36964(19) 0.59150(6) 0.0162(3) Uani 1 1 d . . . . .
H19 H 0.143027 0.431591 0.559152 0.019 Uiso 1 1 calc R U . . .
C20 C -0.0598(2) 0.3525(2) 0.60747(6) 0.0214(3) Uani 1 1 d . . . . .
H20 H -0.075017 0.331509 0.644312 0.026 Uiso 1 1 calc R U . . .
C21 C -0.0771(3) 0.5024(3) 0.59474(9) 0.0358(5) Uani 1 1 d . . . . .
H21A H 0.003656 0.598144 0.614070 0.054 Uiso 1 1 calc R U . . .
H21B H -0.189112 0.478727 0.603058 0.054 Uiso 1 1 calc R U . . .
H21C H -0.056995 0.526556 0.558917 0.054 Uiso 1 1 calc R U . . .
C22 C -0.1873(2) 0.1974(2) 0.57942(7) 0.0271(4) Uani 1 1 d . . . . .
H22A H -0.294737 0.144757 0.597182 0.033 Uiso 1 1 calc R U . . .
H22B H -0.204112 0.226295 0.545114 0.033 Uiso 1 1 calc R U . . .
C23 C -0.1174(2) 0.0812(2) 0.57771(6) 0.0221(3) Uani 1 1 d . . . . .
H23 H -0.159992 0.004884 0.607125 0.027 Uiso 1 1 calc R U . . .
C24 C 0.0693(2) 0.1926(2) 0.58296(6) 0.0177(3) Uani 1 1 d . . . . .
C25 C 0.1742(2) 0.1354(2) 0.57965(6) 0.0223(3) Uani 1 1 d . . . . .
C26 C 0.1148(3) -0.0471(2) 0.57369(8) 0.0321(4) Uani 1 1 d . . . . .
H26A H 0.000453 -0.111919 0.585585 0.048 Uiso 1 1 calc R U . . .
H26B H 0.185638 -0.075747 0.593320 0.048 Uiso 1 1 calc R U . . .
H26C H 0.119853 -0.071899 0.538316 0.048 Uiso 1 1 calc R U . . .
C27 C 0.3617(3) 0.2383(3) 0.57908(8) 0.0297(4) Uani 1 1 d . . . . .
H27A H 0.402168 0.228419 0.612412 0.036 Uiso 1 1 calc R U . . .
H27B H 0.402885 0.187942 0.554536 0.036 Uiso 1 1 calc R U . . .
C28 C 0.4406(2) 0.4210(3) 0.56684(7) 0.0268(4) Uani 1 1 d . . . . .
H28 H 0.561877 0.464223 0.562591 0.032 Uiso 1 1 calc R U . . .


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 C1 1.205(3) . ?
O2 C1 1.356(2) . ?
O2 C4 1.467(2) . ?
O3 H3 0.8400 . ?
O3 C8 1.436(2) . ?
O4 H4 0.8400 . ?
O4 C12 1.431(2) . ?
C1 C2 1.493(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.518(3) . ?
C3 H3A 1.0000 . ?
C3 C4 1.537(2) . ?
C3 C12 1.525(3) . ?
C4 H4A 1.0000 . ?
C4 C5 1.521(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.543(2) . ?
C5 C9 1.523(2) . ?
C6 H6 1.0000 . ?
C6 C7 1.532(3) . ?
C6 C14 1.519(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.510(4) . ?
C8 H8A 1.0000 . ?
C8 C9 1.525(3) . ?
C9 C10 1.333(3) . ?
C10 C11 1.513(4) . ?
C10 C13 1.513(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.515(4) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O5 C15 1.199(3) . ?
O6 C15 1.355(2) . ?
O6 C18 1.467(2) . ?
O7 H7 0.8400 . ?
O7 C28 1.439(2) . ?
O8 H8 0.8400 . ?
O8 C23 1.439(2) . ?
C15 C16 1.504(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.519(3) . ?
C17 H17 1.0000 . ?
C17 C18 1.538(2) . ?
C17 C28 1.527(3) . ?
C18 H18 1.0000 . ?
C18 C19 1.523(2) . ?
C19 H19 1.0000 . ?
C19 C20 1.546(2) . ?
C19 C24 1.524(2) . ?
C20 H20 1.0000 . ?
C20 C21 1.525(3) . ?
C20 C22 1.533(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.520(3) . ?
C23 H23 1.0000 . ?
C23 C24 1.525(2) . ?
C24 C25 1.332(3) . ?
C25 C26 1.514(2) . ?
C25 C27 1.518(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.517(3) . ?
C28 H28 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C4 110.53(15) . . ?
C8 O3 H3 109.5 . . ?
C12 O4 H4 109.5 . . ?
O1 C1 O2 120.9(2) . . ?
O1 C1 C2 128.9(2) . . ?
O2 C1 C2 110.23(18) . . ?
C1 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
C1 C2 C3 103.67(16) . . ?
H2A C2 H2B 109.0 . . ?
C3 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C2 C3 H3A 107.2 . . ?
C2 C3 C4 102.91(17) . . ?
C2 C3 C12 115.34(17) . . ?
C4 C3 H3A 107.2 . . ?
C12 C3 H3A 107.2 . . ?
C12 C3 C4 116.45(15) . . ?
O2 C4 C3 103.44(14) . . ?
O2 C4 H4A 108.9 . . ?
O2 C4 C5 111.09(13) . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 C3 115.42(13) . . ?
C5 C4 H4A 108.9 . . ?
C4 C5 H5 109.2 . . ?
C4 C5 C6 114.38(14) . . ?
C4 C5 C9 110.64(14) . . ?
C6 C5 H5 109.2 . . ?
C9 C5 H5 109.2 . . ?
C9 C5 C6 104.19(14) . . ?
C5 C6 H6 109.2 . . ?
C7 C6 C5 102.36(16) . . ?
C7 C6 H6 109.2 . . ?
C14 C6 C5 114.3(2) . . ?
C14 C6 H6 109.2 . . ?
C14 C6 C7 112.4(2) . . ?
C6 C7 H7A 110.5 . . ?
C6 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C8 C7 C6 106.17(19) . . ?
C8 C7 H7A 110.5 . . ?
C8 C7 H7B 110.5 . . ?
O3 C8 C7 112.4(2) . . ?
O3 C8 H8A 108.8 . . ?
O3 C8 C9 112.86(16) . . ?
C7 C8 H8A 108.8 . . ?
C7 C8 C9 105.10(17) . . ?
C9 C8 H8A 108.8 . . ?
C5 C9 C8 108.20(17) . . ?
C10 C9 C5 128.94(17) . . ?
C10 C9 C8 122.85(19) . . ?
C9 C10 C11 126.47(18) . . ?
C9 C10 C13 121.1(2) . . ?
C13 C10 C11 112.4(2) . . ?
C10 C11 H11A 108.0 . . ?
C10 C11 H11B 108.0 . . ?
C10 C11 C12 117.16(16) . . ?
H11A C11 H11B 107.2 . . ?
C12 C11 H11A 108.0 . . ?
C12 C11 H11B 108.0 . . ?
O4 C12 C3 113.97(17) . . ?
O4 C12 C11 106.77(16) . . ?
O4 C12 H12 107.8 . . ?
C3 C12 H12 107.8 . . ?
C11 C12 C3 112.34(17) . . ?
C11 C12 H12 107.8 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 O6 C18 110.99(14) . . ?
C28 O7 H7 109.5 . . ?
C23 O8 H8 109.5 . . ?
O5 C15 O6 121.56(19) . . ?
O5 C15 C16 128.86(19) . . ?
O6 C15 C16 109.58(17) . . ?
C15 C16 H16A 111.0 . . ?
C15 C16 H16B 111.0 . . ?
C15 C16 C17 103.91(16) . . ?
H16A C16 H16B 109.0 . . ?
C17 C16 H16A 111.0 . . ?
C17 C16 H16B 111.0 . . ?
C16 C17 H17 107.3 . . ?
C16 C17 C18 102.54(16) . . ?
C16 C17 C28 114.91(17) . . ?
C18 C17 H17 107.3 . . ?
C28 C17 H17 107.3 . . ?
C28 C17 C18 116.86(15) . . ?
O6 C18 C17 103.95(13) . . ?
O6 C18 H18 109.0 . . ?
O6 C18 C19 111.05(14) . . ?
C17 C18 H18 109.0 . . ?
C19 C18 C17 114.77(14) . . ?
C19 C18 H18 109.0 . . ?
C18 C19 H19 109.1 . . ?
C18 C19 C20 114.63(13) . . ?
C18 C19 C24 110.15(13) . . ?
C20 C19 H19 109.1 . . ?
C24 C19 H19 109.1 . . ?
C24 C19 C20 104.67(13) . . ?
C19 C20 H20 109.2 . . ?
C21 C20 C19 114.04(16) . . ?
C21 C20 H20 109.2 . . ?
C21 C20 C22 111.64(16) . . ?
C22 C20 C19 103.26(14) . . ?
C22 C20 H20 109.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 110.5 . . ?
C20 C22 H22B 110.5 . . ?
H22A C22 H22B 108.7 . . ?
C23 C22 C20 106.32(15) . . ?
C23 C22 H22A 110.5 . . ?
C23 C22 H22B 110.5 . . ?
O8 C23 C22 111.88(15) . . ?
O8 C23 H23 109.0 . . ?
O8 C23 C24 112.71(14) . . ?
C22 C23 H23 109.0 . . ?
C22 C23 C24 105.20(14) . . ?
C24 C23 H23 109.0 . . ?
C19 C24 C23 108.67(14) . . ?
C25 C24 C19 128.71(16) . . ?
C25 C24 C23 122.61(16) . . ?
C24 C25 C26 121.96(18) . . ?
C24 C25 C27 126.37(16) . . ?
C26 C25 C27 111.63(17) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 107.8 . . ?
C25 C27 H27B 107.8 . . ?
H27A C27 H27B 107.1 . . ?
C28 C27 C25 118.16(16) . . ?
C28 C27 H27A 107.8 . . ?
C28 C27 H27B 107.8 . . ?
O7 C28 C17 113.44(16) . . ?
O7 C28 C27 108.75(15) . . ?
O7 C28 H28 107.1 . . ?
C17 C28 H28 107.1 . . ?
C27 C28 C17 112.97(16) . . ?
C27 C28 H28 107.1 . . ?

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
O3 H3 O8 0.84 1.92 2.7460(19) 169.4 1_665 yes
O4 H4 O7 0.84 1.97 2.8090(19) 172.1 1_665 yes
O7 H7 O3 0.84 1.85 2.6768(19) 167.5 . yes
O8 H8 O4 0.84 1.98 2.7941(18) 161.7 1_445 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
O1 C1 C2 C3 164.5(2) . . . . ?
O2 C1 C2 C3 -15.3(2) . . . . ?
O2 C4 C5 C6 -46.40(19) . . . . ?
O2 C4 C5 C9 -163.68(13) . . . . ?
O3 C8 C9 C5 125.6(2) . . . . ?
O3 C8 C9 C10 -55.3(3) . . . . ?
C1 O2 C4 C3 21.63(19) . . . . ?
C1 O2 C4 C5 -102.79(17) . . . . ?
C1 C2 C3 C4 27.18(19) . . . . ?
C1 C2 C3 C12 155.07(17) . . . . ?
C2 C3 C4 O2 -29.63(16) . . . . ?
C2 C3 C4 C5 91.93(17) . . . . ?
C2 C3 C12 O4 -49.1(2) . . . . ?
C2 C3 C12 C11 -170.74(18) . . . . ?
C3 C4 C5 C6 -163.74(17) . . . . ?
C3 C4 C5 C9 78.98(18) . . . . ?
C4 O2 C1 O1 176.0(2) . . . . ?
C4 O2 C1 C2 -4.2(2) . . . . ?
C4 C3 C12 O4 71.6(2) . . . . ?
C4 C3 C12 C11 -50.0(2) . . . . ?
C4 C5 C6 C7 -155.28(19) . . . . ?
C4 C5 C6 C14 82.9(2) . . . . ?
C4 C5 C9 C8 143.36(14) . . . . ?
C4 C5 C9 C10 -35.7(2) . . . . ?
C5 C6 C7 C8 37.1(2) . . . . ?
C5 C9 C10 C11 -7.3(3) . . . . ?
C5 C9 C10 C13 175.71(18) . . . . ?
C6 C5 C9 C8 19.98(18) . . . . ?
C6 C5 C9 C10 -159.07(18) . . . . ?
C6 C7 C8 O3 -148.02(18) . . . . ?
C6 C7 C8 C9 -24.9(2) . . . . ?
C7 C8 C9 C5 2.8(2) . . . . ?
C7 C8 C9 C10 -178.10(18) . . . . ?
C8 C9 C10 C11 173.78(18) . . . . ?
C8 C9 C10 C13 -3.2(3) . . . . ?
C9 C5 C6 C7 -34.4(2) . . . . ?
C9 C5 C6 C14 -156.22(18) . . . . ?
C9 C10 C11 C12 -21.0(3) . . . . ?
C10 C11 C12 O4 -51.2(2) . . . . ?
C10 C11 C12 C3 74.5(2) . . . . ?
C12 C3 C4 O2 -156.82(16) . . . . ?
C12 C3 C4 C5 -35.3(2) . . . . ?
C13 C10 C11 C12 156.26(18) . . . . ?
C14 C6 C7 C8 160.2(2) . . . . ?
O5 C15 C16 C17 163.2(2) . . . . ?
O6 C15 C16 C17 -17.2(2) . . . . ?
O6 C18 C19 C20 -44.26(19) . . . . ?
O6 C18 C19 C24 -161.97(13) . . . . ?
O8 C23 C24 C19 126.27(15) . . . . ?
O8 C23 C24 C25 -53.1(2) . . . . ?
C15 O6 C18 C17 19.70(19) . . . . ?
C15 O6 C18 C19 -104.24(17) . . . . ?
C15 C16 C17 C18 27.7(2) . . . . ?
C15 C16 C17 C28 155.58(16) . . . . ?
C16 C17 C18 O6 -28.86(18) . . . . ?
C16 C17 C18 C19 92.63(18) . . . . ?
C16 C17 C28 O7 -46.0(2) . . . . ?
C16 C17 C28 C27 -170.31(17) . . . . ?
C17 C18 C19 C20 -161.78(15) . . . . ?
C17 C18 C19 C24 80.51(18) . . . . ?
C18 O6 C15 O5 177.91(19) . . . . ?
C18 O6 C15 C16 -1.7(2) . . . . ?
C18 C17 C28 O7 74.3(2) . . . . ?
C18 C17 C28 C27 -50.1(2) . . . . ?
C18 C19 C20 C21 86.63(18) . . . . ?
C18 C19 C20 C22 -152.04(15) . . . . ?
C18 C19 C24 C23 140.82(14) . . . . ?
C18 C19 C24 C25 -39.8(2) . . . . ?
C19 C20 C22 C23 34.59(18) . . . . ?
C19 C24 C25 C26 176.75(17) . . . . ?
C19 C24 C25 C27 -5.9(3) . . . . ?
C20 C19 C24 C23 17.11(17) . . . . ?
C20 C19 C24 C25 -163.54(17) . . . . ?
C20 C22 C23 O8 -146.83(14) . . . . ?
C20 C22 C23 C24 -24.13(18) . . . . ?
C21 C20 C22 C23 157.53(16) . . . . ?
C22 C23 C24 C19 4.10(17) . . . . ?
C22 C23 C24 C25 -175.29(16) . . . . ?
C23 C24 C25 C26 -4.0(3) . . . . ?
C23 C24 C25 C27 173.35(17) . . . . ?
C24 C19 C20 C21 -152.60(15) . . . . ?
C24 C19 C20 C22 -31.26(17) . . . . ?
C24 C25 C27 C28 -18.1(3) . . . . ?
C25 C27 C28 O7 -55.4(2) . . . . ?
C25 C27 C28 C17 71.5(2) . . . . ?
C26 C25 C27 C28 159.44(17) . . . . ?
C28 C17 C18 O6 -155.46(17) . . . . ?
C28 C17 C18 C19 -34.0(2) . . . . ?

