# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_renpl_1005
_audit_block_doi                 10.5517/ccdc.csd.cc251stv
_database_code_depnum_ccdc_archive 'CCDC 1997727'
loop_
_audit_author_name
_audit_author_address
'Panlong Ren'
;Lanzhou University
China
;
_audit_update_record             
;
2020-04-18 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_audit_creation_date             2020-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H12 O3'
_chemical_formula_sum            'C11 H12 O3'
_chemical_formula_weight         192.21
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.5792(5)
_cell_length_b                   17.2620(8)
_cell_length_c                   7.5865(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.065(5)
_cell_angle_gamma                90
_cell_volume                     988.68(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1488
_cell_measurement_temperature    293.61(10)
_cell_measurement_theta_max      68.3540
_cell_measurement_theta_min      5.1110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5226
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        66.568
_diffrn_reflns_theta_max         66.568
_diffrn_reflns_theta_min         5.124
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.61(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  69.00   1.00    1.00    --    0.00  57.00 120.00   90
  2  ω    -47.00  12.00   1.00    1.00    --    0.00 108.00 -68.00   59
  3  ω     33.00 123.00   1.00    1.00    --   54.00  57.00-150.00   90
  4  ω     23.00 111.00   1.00    1.00    --   54.00-125.00 -90.00   88
  5  ω     10.00 127.00   1.00    1.00    --   54.00  19.00 -30.00  117
  6  ω     38.00 138.00   1.00    1.00    --  108.00 -77.00  90.00  100
  7  ω     36.00 116.00   1.00    1.00    --  108.00-111.00  60.00   80
  8  ω     86.00 178.00   1.00    1.00    --  108.00  50.00 -60.00   92
  9  ω     86.00 178.00   1.00    1.00    --  108.00  50.00-180.00   92
 10  ω     57.00 151.00   1.00    1.00    --  108.00 178.00  60.00   94
 11  ω    100.00 178.00   1.00    1.00    --  108.00 111.00-150.00   78
 12  ω     57.00 151.00   1.00    1.00    --  108.00 178.00   0.00   94
 13  ω    -21.00  69.00   1.00    1.00    --    0.00  57.00-150.00   90
 14  ω    -70.00  30.00   1.00    1.00    --    0.00 -77.00  90.00  100
 15  ω     24.00 124.00   1.00    1.00    --   54.00  77.00  90.00  100
 16  ω    -15.00  16.00   1.00    1.00    --   54.00 -57.00 -30.00   31
 17  ω     33.00 123.00   1.00    1.00    --   54.00  57.00  30.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0911488000
_diffrn_orient_matrix_UB_12      -0.0780468000
_diffrn_orient_matrix_UB_13      0.0294328000
_diffrn_orient_matrix_UB_21      -0.0696438000
_diffrn_orient_matrix_UB_22      0.0318698000
_diffrn_orient_matrix_UB_23      0.1705158000
_diffrn_orient_matrix_UB_31      -0.1689822000
_diffrn_orient_matrix_UB_32      0.0289885000
_diffrn_orient_matrix_UB_33      -0.1078926000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1357
_reflns_number_total             1716
_reflns_odcompleteness_completeness 98.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1716
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.033
_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)+(0.0635P)²+0.2287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1279
_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 Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C11(H11), C12(H12), C1AA(H1AA)
2.c Idealised Me refined as rotating group:
 C0AA(H0AA,H0AB,H0AC)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.09843(17) 0.20791(7) 0.66652(15) 0.0516(4) Uani 1 1 d . . . . .
H1 H 0.158918 0.228637 0.748237 0.077 Uiso 1 1 calc GR . . . .
O2 O -0.1942(2) 0.22264(8) 0.43479(19) 0.0646(4) Uani 1 1 d . . . . .
C3 C -0.2458(2) 0.15668(11) 0.5376(2) 0.0503(5) Uani 1 1 d . . . . .
C4 C 0.0442(2) 0.13196(10) 0.7211(2) 0.0427(4) Uani 1 1 d . . . . .
C5 C -0.0882(2) 0.10268(10) 0.5737(2) 0.0444(4) Uani 1 1 d . . . . .
H5A H -0.028891 0.096942 0.466268 0.053 Uiso 1 1 calc R . . . .
H5B H -0.130513 0.051995 0.605680 0.053 Uiso 1 1 calc R . . . .
C6 C -0.0489(3) 0.13984(11) 0.8870(2) 0.0524(5) Uani 1 1 d . . . . .
C7 C 0.2064(3) 0.08304(12) 0.7434(3) 0.0632(5) Uani 1 1 d . . . . .
H7 H 0.262710 0.070255 0.643296 0.076 Uiso 1 1 calc R . . . .
C8 C -0.2212(3) 0.17684(14) 0.8634(3) 0.0716(6) Uani 1 1 d . . . . .
H8 H -0.271613 0.195170 0.962746 0.086 Uiso 1 1 calc R . . . .
O9 O 0.2568(3) 0.04928(13) 1.2053(3) 0.1297(10) Uani 1 1 d . . . . .
C10 C 0.1910(4) 0.07177(15) 1.0610(3) 0.0851(9) Uani 1 1 d . . . . .
C11 C 0.0247(3) 0.11370(14) 1.0424(3) 0.0744(7) Uani 1 1 d . . . . .
H11 H -0.033573 0.122855 1.143257 0.089 Uiso 1 1 calc R . . . .
C12 C -0.3096(3) 0.18559(13) 0.7067(3) 0.0677(6) Uani 1 1 d . . . . .
H12 H -0.417865 0.211239 0.701097 0.081 Uiso 1 1 calc R . . . .
C0AA C -0.3952(3) 0.11753(14) 0.4234(3) 0.0772(7) Uani 1 1 d . . . . .
H0AA H -0.490458 0.153633 0.398297 0.116 Uiso 1 1 calc GR . . . .
H0AB H -0.437136 0.073673 0.485359 0.116 Uiso 1 1 calc GR . . . .
H0AC H -0.352227 0.100595 0.314499 0.116 Uiso 1 1 calc GR . . . .
C1AA C 0.2741(3) 0.05693(15) 0.8986(4) 0.0839(8) Uani 1 1 d . . . . .
H1AA H 0.378124 0.028142 0.904153 0.101 Uiso 1 1 calc R . . . .
H2 H -0.104(3) 0.2424(15) 0.498(3) 0.089(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C4 1.445(2) . ?
O2 C3 1.453(2) . ?
O2 H2 0.87(3) . ?
C3 C5 1.521(2) . ?
C3 C12 1.496(3) . ?
C3 C0AA 1.522(3) . ?
C4 C5 1.522(2) . ?
C4 C6 1.503(2) . ?
C4 C7 1.488(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C8 1.451(3) . ?
C6 C11 1.337(3) . ?
C7 H7 0.9300 . ?
C7 C1AA 1.321(3) . ?
C8 H8 0.9300 . ?
C8 C12 1.321(3) . ?
O9 C10 1.226(2) . ?
C10 C11 1.450(4) . ?
C10 C1AA 1.455(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C0AA H0AA 0.9600 . ?
C0AA H0AB 0.9600 . ?
C0AA H0AC 0.9600 . ?
C1AA H1AA 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 H1 109.5 . . ?
C3 O2 H2 104.4(17) . . ?
O2 C3 C5 109.41(14) . . ?
O2 C3 C12 108.76(16) . . ?
O2 C3 C0AA 105.34(16) . . ?
C5 C3 C0AA 111.30(17) . . ?
C12 C3 C5 110.99(16) . . ?
C12 C3 C0AA 110.84(17) . . ?
O1 C4 C5 106.05(13) . . ?
O1 C4 C6 108.93(14) . . ?
O1 C4 C7 107.11(14) . . ?
C6 C4 C5 108.52(14) . . ?
C7 C4 C5 112.31(15) . . ?
C7 C4 C6 113.60(16) . . ?
C3 C5 C4 112.67(14) . . ?
C3 C5 H5A 109.1 . . ?
C3 C5 H5B 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C8 C6 C4 114.87(16) . . ?
C11 C6 C4 121.2(2) . . ?
C11 C6 C8 124.0(2) . . ?
C4 C7 H7 118.4 . . ?
C1AA C7 C4 123.1(2) . . ?
C1AA C7 H7 118.4 . . ?
C6 C8 H8 118.6 . . ?
C12 C8 C6 122.76(18) . . ?
C12 C8 H8 118.6 . . ?
O9 C10 C11 121.8(3) . . ?
O9 C10 C1AA 121.9(3) . . ?
C11 C10 C1AA 116.31(18) . . ?
C6 C11 C10 123.1(2) . . ?
C6 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C3 C12 H12 118.1 . . ?
C8 C12 C3 123.86(19) . . ?
C8 C12 H12 118.1 . . ?
C3 C0AA H0AA 109.5 . . ?
C3 C0AA H0AB 109.5 . . ?
C3 C0AA H0AC 109.5 . . ?
H0AA C0AA H0AB 109.5 . . ?
H0AA C0AA H0AC 109.5 . . ?
H0AB C0AA H0AC 109.5 . . ?
C7 C1AA C10 122.1(2) . . ?
C7 C1AA H1AA 119.0 . . ?
C10 C1AA H1AA 119.0 . . ?

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 C4 C5 C3 -57.58(18) . . . . ?
O1 C4 C6 C8 69.9(2) . . . . ?
O1 C4 C6 C11 -110.51(19) . . . . ?
O1 C4 C7 C1AA 112.5(2) . . . . ?
O2 C3 C5 C4 77.71(18) . . . . ?
O2 C3 C12 C8 -108.9(2) . . . . ?
C4 C6 C8 C12 16.1(3) . . . . ?
C4 C6 C11 C10 -4.3(3) . . . . ?
C4 C7 C1AA C10 2.3(4) . . . . ?
C5 C3 C12 C8 11.5(3) . . . . ?
C5 C4 C6 C8 -45.2(2) . . . . ?
C5 C4 C6 C11 134.46(19) . . . . ?
C5 C4 C7 C1AA -131.5(2) . . . . ?
C6 C4 C5 C3 59.31(19) . . . . ?
C6 C4 C7 C1AA -7.8(3) . . . . ?
C6 C8 C12 C3 1.9(4) . . . . ?
C7 C4 C5 C3 -174.26(15) . . . . ?
C7 C4 C6 C8 -170.85(17) . . . . ?
C7 C4 C6 C11 8.8(3) . . . . ?
C8 C6 C11 C10 175.3(2) . . . . ?
O9 C10 C11 C6 179.0(2) . . . . ?
O9 C10 C1AA C7 -177.9(2) . . . . ?
C11 C6 C8 C12 -163.5(2) . . . . ?
C11 C10 C1AA C7 2.9(4) . . . . ?
C12 C3 C5 C4 -42.3(2) . . . . ?
C0AA C3 C5 C4 -166.29(16) . . . . ?
C0AA C3 C12 C8 135.8(2) . . . . ?
C1AA C10 C11 C6 -1.8(3) . . . . ?

_olex2_date_sample_data_collection 2020-01-07
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.261
_oxdiff_exptl_absorpt_empirical_full_min 0.734
####################################################################### 
# 
# 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_renpl_1204
_database_code_depnum_ccdc_archive 'CCDC 1997730'
loop_
_audit_author_name
_audit_author_address
'Panlong Ren'
;Lanzhou University
China
;
_audit_update_record             
;
2020-04-18 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_audit_creation_date             2019-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H20 O4, H2 O'
_chemical_formula_sum            'C16 H22 O5'
_chemical_formula_weight         294.33
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     'nature product'
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           54
_space_group_name_H-M_alt        'P c c a'
_space_group_name_Hall           '-P 2a 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'x+1/2, -y, -z+1/2'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'-x-1/2, y, z-1/2'
'x, -y, z-1/2'

_cell_length_a                   32.6901(5)
_cell_length_b                   12.36143(17)
_cell_length_c                   7.35394(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2971.70(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8065
_cell_measurement_temperature    294.04(10)
_cell_measurement_theta_max      69.5770
_cell_measurement_theta_min      7.4840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            24301
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.581
_diffrn_reflns_theta_max         66.581
_diffrn_reflns_theta_min         3.576
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.04(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  69.00   1.00    1.00    --    0.00  57.00 -90.00   90
  2  ω    -21.00  69.00   1.00    1.00    --    0.00  57.00   0.00   90
  3  ω     24.00 124.00   1.00    2.00    --   54.00  77.00  30.00  100
  4  ω    -15.00  75.00   1.00    2.00    --   54.00 -57.00 -30.00   90
  5  ω     33.00 123.00   1.00    2.00    --   54.00  57.00-180.00   90
  6  ω    -16.00  84.00   1.00    2.00    --   54.00 -77.00 -90.00  100
  7  ω     36.00 116.00   1.00    3.00    --  108.00-111.00 150.00   80
  8  ω     35.00 178.00   1.00    3.00    --  108.00 -12.00   0.00  143
  9  ω     36.00 146.00   1.00    3.00    --  108.00 -91.00   0.00  110
 10  ω     38.00 130.00   1.00    3.00    --  108.00 -50.00 -30.00   92
 11  ω     35.00 142.00   1.00    3.00    --  108.00 -25.00 -90.00  107
 12  ω    -55.00   1.00   1.00    1.00    --    0.00 121.00 135.00   56
 13  ω     77.00 123.00   1.00    2.00    --   54.00 153.00 -65.00   46
 14  ω     33.00 123.00   1.00    2.00    --   54.00  57.00 -60.00   90
 15  ω     36.00 119.00   1.00    3.00    --  108.00-119.00 -39.00   83
 16  ω     38.00 130.00   1.00    3.00    --  108.00 -50.00 120.00   92
 17  ω     74.00 178.00   1.00    3.00    --  108.00  25.00-180.00  104
 18  ω     74.00 178.00   1.00    3.00    --  108.00  25.00  90.00  104
 19  ω    -70.00  30.00   1.00    1.00    --    0.00 -77.00 -60.00  100
 20  ω     24.00 124.00   1.00    2.00    --   54.00  77.00-120.00  100
 21  ω     33.00 123.00   1.00    2.00    --   54.00  57.00 120.00   90
 22  ω     74.00 101.00   1.00    3.00    --  108.00  25.00 -90.00   27
 23  ω     78.00 178.00   1.00    3.00    --  108.00  77.00  90.00  100
 24  ω     74.00 178.00   1.00    3.00    --  108.00  25.00   0.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0467156000
_diffrn_orient_matrix_UB_12      0.0071642000
_diffrn_orient_matrix_UB_13      0.0246830000
_diffrn_orient_matrix_UB_21      -0.0020219000
_diffrn_orient_matrix_UB_22      -0.1235702000
_diffrn_orient_matrix_UB_23      0.0259904000
_diffrn_orient_matrix_UB_31      0.0058325000
_diffrn_orient_matrix_UB_32      0.0146367000
_diffrn_orient_matrix_UB_33      0.2063998000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2312
_reflns_number_total             2633
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2633
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.028
_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)+(0.0548P)²+1.0401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1081
_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, All O(H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H2A(0.5) H2B(0.5)
3.a Free rotating group:
 O1(H1A,H1B), O2(H2A,H2B)
3.b Ternary CH refined with riding coordinates:
 C6BA(H6BA), C4AA(H4AA), C6AA(H6AA)
3.c Secondary CH2 refined with riding coordinates:
 C7AA(H7AA,H7AB), C21(H21A,H21B)
3.d Aromatic/amide H refined with riding coordinates:
 C1AA(H1AA), C2AA(H2AA)
3.e Idealised Me refined as rotating group:
 C9AA(H9AA,H9AB,H9AC), C0BA(H0BA,H0BB,H0BC), C22(H22A,H22B,H22C)
3.f Idealised tetrahedral OH refined as rotating group:
 O1BA(H1BA), O3BA(H3BA)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1BA O 0.45780(3) 0.39182(10) 0.07864(16) 0.0445(3) Uani 1 1 d . . . . .
H1BA H 0.468118 0.441881 0.135624 0.067 Uiso 1 1 calc GR . . . .
O2BA O 0.41905(3) 0.07869(8) -0.26754(16) 0.0442(3) Uani 1 1 d . . . . .
O3BA O 0.29215(3) 0.36564(10) 0.21097(18) 0.0483(3) Uani 1 1 d . . . . .
H3BA H 0.286355 0.404946 0.297028 0.072 Uiso 1 1 calc GR . . . .
O4BA O 0.43717(3) 0.25462(8) -0.22856(15) 0.0415(3) Uani 1 1 d . . . . .
C5BA C 0.35196(4) 0.29551(11) 0.0612(2) 0.0331(3) Uani 1 1 d . . . . .
C6BA C 0.41896(5) 0.21696(12) -0.0607(2) 0.0343(3) Uani 1 1 d . . . . .
H6BA H 0.440865 0.192343 0.020338 0.041 Uiso 1 1 calc R . . . .
C7BA C 0.39460(4) 0.30312(11) 0.03606(19) 0.0308(3) Uani 1 1 d . . . . .
C0AA C 0.41654(4) 0.38880(12) 0.11215(19) 0.0330(3) Uani 1 1 d . . . . .
C1AA C 0.39736(5) 0.46645(12) 0.2163(2) 0.0386(4) Uani 1 1 d . . . . .
H1AA H 0.412107 0.524348 0.263484 0.046 Uiso 1 1 calc R . . . .
C2AA C 0.35600(5) 0.45699(12) 0.2496(2) 0.0387(4) Uani 1 1 d . . . . .
H2AA H 0.342960 0.507662 0.322934 0.046 Uiso 1 1 calc R . . . .
C3AA C 0.32746(5) 0.20292(12) -0.0276(2) 0.0397(4) Uani 1 1 d . . . . .
C4AA C 0.35235(5) 0.15378(12) -0.1875(2) 0.0386(4) Uani 1 1 d . . . . .
H4AA H 0.337959 0.088864 -0.229421 0.046 Uiso 1 1 calc R . . . .
C5AA C 0.33378(5) 0.37310(11) 0.1751(2) 0.0353(3) Uani 1 1 d . . . . .
C6AA C 0.39449(5) 0.11945(11) -0.1213(2) 0.0371(4) Uani 1 1 d . . . . .
H6AA H 0.392296 0.066138 -0.023190 0.044 Uiso 1 1 calc R . . . .
C7AA C 0.35580(5) 0.23185(13) -0.3490(2) 0.0437(4) Uani 1 1 d . . . . .
H7AA H 0.330640 0.228890 -0.418667 0.052 Uiso 1 1 calc R . . . .
H7AB H 0.358747 0.304962 -0.302861 0.052 Uiso 1 1 calc R . . . .
C8AA C 0.42900(5) 0.17403(13) -0.3671(2) 0.0431(4) Uani 1 1 d . . . . .
C9AA C 0.28593(5) 0.23979(15) -0.1071(3) 0.0520(5) Uani 1 1 d . . . . .
H9AA H 0.266970 0.252497 -0.009694 0.078 Uiso 1 1 calc GR . . . .
H9AB H 0.275365 0.184443 -0.185663 0.078 Uiso 1 1 calc GR . . . .
H9AC H 0.289688 0.305312 -0.175112 0.078 Uiso 1 1 calc GR . . . .
C0BA C 0.31898(6) 0.11725(14) 0.1188(3) 0.0555(5) Uani 1 1 d . . . . .
H0BA H 0.344449 0.090321 0.165486 0.083 Uiso 1 1 calc GR . . . .
H0BB H 0.303688 0.058695 0.066556 0.083 Uiso 1 1 calc GR . . . .
H0BC H 0.303513 0.149173 0.215929 0.083 Uiso 1 1 calc GR . . . .
C21 C 0.39175(6) 0.20704(15) -0.4753(2) 0.0505(4) Uani 1 1 d . . . . .
H21A H 0.384252 0.149133 -0.557850 0.061 Uiso 1 1 calc R . . . .
H21B H 0.398105 0.270602 -0.547350 0.061 Uiso 1 1 calc R . . . .
C22 C 0.46671(6) 0.15475(18) -0.4804(3) 0.0625(5) Uani 1 1 d . . . . .
H22A H 0.488245 0.127500 -0.404348 0.094 Uiso 1 1 calc GR . . . .
H22B H 0.475239 0.221542 -0.535162 0.094 Uiso 1 1 calc GR . . . .
H22C H 0.460687 0.102913 -0.573846 0.094 Uiso 1 1 calc GR . . . .
O1 O 0.500000 0.44233(13) -0.250000 0.0420(4) Uani 1 2 d S T P . .
H1A H 0.490958 0.414055 -0.152637 0.063 Uiso 0.5 1 d G . . . .
H1B H 0.516851 0.396093 -0.291366 0.063 Uiso 0.5 1 d G . . . .
O2 O 0.250000 0.500000 -0.0425(2) 0.0514(4) Uani 1 2 d S T P . .
H2A H 0.234426 0.535447 0.028297 0.077 Uiso 0.5 1 d G . . . .
H2B H 0.259824 0.449984 0.023687 0.077 Uiso 0.5 1 d G . . . .


_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
O1BA H1BA 0.8200 . ?
O1BA C0AA 1.3716(18) . ?
O2BA C6AA 1.4334(19) . ?
O2BA C8AA 1.425(2) . ?
O3BA H3BA 0.8200 . ?
O3BA C5AA 1.3892(18) . ?
O4BA C6BA 1.4473(19) . ?
O4BA C8AA 1.4499(19) . ?
C5BA C7BA 1.409(2) . ?
C5BA C3AA 1.542(2) . ?
C5BA C5AA 1.405(2) . ?
C6BA H6BA 0.9800 . ?
C6BA C7BA 1.508(2) . ?
C6BA C6AA 1.514(2) . ?
C7BA C0AA 1.396(2) . ?
C0AA C1AA 1.379(2) . ?
C1AA H1AA 0.9300 . ?
C1AA C2AA 1.379(2) . ?
C2AA H2AA 0.9300 . ?
C2AA C5AA 1.380(2) . ?
C3AA C4AA 1.553(2) . ?
C3AA C9AA 1.547(2) . ?
C3AA C0BA 1.535(2) . ?
C4AA H4AA 0.9800 . ?
C4AA C6AA 1.521(2) . ?
C4AA C7AA 1.534(2) . ?
C6AA H6AA 0.9800 . ?
C7AA H7AA 0.9700 . ?
C7AA H7AB 0.9700 . ?
C7AA C21 1.529(3) . ?
C8AA C21 1.511(2) . ?
C8AA C22 1.507(2) . ?
C9AA H9AA 0.9600 . ?
C9AA H9AB 0.9600 . ?
C9AA H9AC 0.9600 . ?
C0BA H0BA 0.9600 . ?
C0BA H0BB 0.9600 . ?
C0BA H0BC 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O1 H1A 0.85(3) 4_654 ?
O1 H1A 0.8498 . ?
O1 H1B 0.85(5) 4_654 ?
O1 H1B 0.8501 . ?
O2 H2A 0.8501 . ?
O2 H2A 0.85(11) 2_565 ?
O2 H2B 0.85(10) 2_565 ?
O2 H2B 0.8501 . ?

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
C0AA O1BA H1BA 109.5 . . ?
C8AA O2BA C6AA 102.86(11) . . ?
C5AA O3BA H3BA 109.5 . . ?
C6BA O4BA C8AA 107.62(11) . . ?
C7BA C5BA C3AA 120.50(13) . . ?
C5AA C5BA C7BA 116.82(13) . . ?
C5AA C5BA C3AA 122.64(13) . . ?
O4BA C6BA H6BA 108.5 . . ?
O4BA C6BA C7BA 113.10(12) . . ?
O4BA C6BA C6AA 102.84(12) . . ?
C7BA C6BA H6BA 108.5 . . ?
C7BA C6BA C6AA 114.97(13) . . ?
C6AA C6BA H6BA 108.5 . . ?
C5BA C7BA C6BA 122.49(12) . . ?
C0AA C7BA C5BA 120.40(13) . . ?
C0AA C7BA C6BA 116.98(13) . . ?
O1BA C0AA C7BA 116.98(13) . . ?
O1BA C0AA C1AA 121.87(13) . . ?
C1AA C0AA C7BA 121.15(14) . . ?
C0AA C1AA H1AA 120.5 . . ?
C2AA C1AA C0AA 119.03(14) . . ?
C2AA C1AA H1AA 120.5 . . ?
C1AA C2AA H2AA 119.7 . . ?
C1AA C2AA C5AA 120.64(14) . . ?
C5AA C2AA H2AA 119.7 . . ?
C5BA C3AA C4AA 109.81(13) . . ?
C5BA C3AA C9AA 113.40(13) . . ?
C9AA C3AA C4AA 106.80(14) . . ?
C0BA C3AA C5BA 107.97(14) . . ?
C0BA C3AA C4AA 110.83(13) . . ?
C0BA C3AA C9AA 108.04(14) . . ?
C3AA C4AA H4AA 107.9 . . ?
C6AA C4AA C3AA 109.95(13) . . ?
C6AA C4AA H4AA 107.9 . . ?
C6AA C4AA C7AA 110.88(13) . . ?
C7AA C4AA C3AA 112.23(12) . . ?
C7AA C4AA H4AA 107.9 . . ?
O3BA C5AA C5BA 118.83(13) . . ?
C2AA C5AA O3BA 119.36(14) . . ?
C2AA C5AA C5BA 121.80(14) . . ?
O2BA C6AA C6BA 101.81(12) . . ?
O2BA C6AA C4AA 111.44(13) . . ?
O2BA C6AA H6AA 110.9 . . ?
C6BA C6AA C4AA 110.52(12) . . ?
C6BA C6AA H6AA 110.9 . . ?
C4AA C6AA H6AA 110.9 . . ?
C4AA C7AA H7AA 108.8 . . ?
C4AA C7AA H7AB 108.8 . . ?
H7AA C7AA H7AB 107.7 . . ?
C21 C7AA C4AA 113.62(14) . . ?
C21 C7AA H7AA 108.8 . . ?
C21 C7AA H7AB 108.8 . . ?
O2BA C8AA O4BA 104.42(12) . . ?
O2BA C8AA C21 108.07(14) . . ?
O2BA C8AA C22 109.87(15) . . ?
O4BA C8AA C21 109.45(13) . . ?
O4BA C8AA C22 110.27(14) . . ?
C22 C8AA C21 114.27(16) . . ?
C3AA C9AA H9AA 109.5 . . ?
C3AA C9AA H9AB 109.5 . . ?
C3AA C9AA H9AC 109.5 . . ?
H9AA C9AA H9AB 109.5 . . ?
H9AA C9AA H9AC 109.5 . . ?
H9AB C9AA H9AC 109.5 . . ?
C3AA C0BA H0BA 109.5 . . ?
C3AA C0BA H0BB 109.5 . . ?
C3AA C0BA H0BC 109.5 . . ?
H0BA C0BA H0BB 109.5 . . ?
H0BA C0BA H0BC 109.5 . . ?
H0BB C0BA H0BC 109.5 . . ?
C7AA C21 H21A 109.5 . . ?
C7AA C21 H21B 109.5 . . ?
C8AA C21 C7AA 110.70(14) . . ?
C8AA C21 H21A 109.5 . . ?
C8AA C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C8AA C22 H22A 109.5 . . ?
C8AA C22 H22B 109.5 . . ?
C8AA C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H1A O1 H1A 131.4 . 4_654 ?
H1A O1 H1B 104.5 . . ?
H1A O1 H1B 104.5 4_654 4_654 ?
H1A O1 H1B 36.5 . 4_654 ?
H1B O1 H1A 36.5 . 4_654 ?
H1B O1 H1B 95.5 . 4_654 ?
H2A O2 H2A 104.4 . 2_565 ?
H2A O2 H2B 104.5 2_565 2_565 ?
H2A O2 H2B 17.8 . 2_565 ?
H2A O2 H2B 104.5 . . ?
H2B O2 H2A 17.8 . 2_565 ?
H2B O2 H2B 110.1 . 2_565 ?

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
O1BA C0AA C1AA C2AA -178.03(14) . . . . ?
O2BA C8AA C21 C7AA 60.97(17) . . . . ?
O4BA C6BA C7BA C5BA 115.13(15) . . . . ?
O4BA C6BA C7BA C0AA -69.18(17) . . . . ?
O4BA C6BA C6AA O2BA 32.76(14) . . . . ?
O4BA C6BA C6AA C4AA -85.73(14) . . . . ?
O4BA C8AA C21 C7AA -52.16(19) . . . . ?
C5BA C7BA C0AA O1BA -178.74(13) . . . . ?
C5BA C7BA C0AA C1AA 1.4(2) . . . . ?
C5BA C3AA C4AA C6AA 54.44(16) . . . . ?
C5BA C3AA C4AA C7AA -69.47(16) . . . . ?
C6BA O4BA C8AA O2BA -18.86(15) . . . . ?
C6BA O4BA C8AA C21 96.63(15) . . . . ?
C6BA O4BA C8AA C22 -136.84(15) . . . . ?
C6BA C7BA C0AA O1BA 5.5(2) . . . . ?
C6BA C7BA C0AA C1AA -174.43(13) . . . . ?
C7BA C5BA C3AA C4AA -19.68(19) . . . . ?
C7BA C5BA C3AA C9AA -139.06(16) . . . . ?
C7BA C5BA C3AA C0BA 101.27(17) . . . . ?
C7BA C5BA C5AA O3BA -176.91(13) . . . . ?
C7BA C5BA C5AA C2AA 4.1(2) . . . . ?
C7BA C6BA C6AA O2BA 156.14(12) . . . . ?
C7BA C6BA C6AA C4AA 37.64(18) . . . . ?
C7BA C0AA C1AA C2AA 1.9(2) . . . . ?
C0AA C1AA C2AA C5AA -2.1(2) . . . . ?
C1AA C2AA C5AA O3BA -179.99(14) . . . . ?
C1AA C2AA C5AA C5BA -1.0(2) . . . . ?
C3AA C5BA C7BA C6BA -6.4(2) . . . . ?
C3AA C5BA C7BA C0AA 178.09(14) . . . . ?
C3AA C5BA C5AA O3BA 0.7(2) . . . . ?
C3AA C5BA C5AA C2AA -178.29(14) . . . . ?
C3AA C4AA C6AA O2BA -177.08(11) . . . . ?
C3AA C4AA C6AA C6BA -64.63(16) . . . . ?
C3AA C4AA C7AA C21 158.52(14) . . . . ?
C4AA C7AA C21 C8AA -39.65(19) . . . . ?
C5AA C5BA C7BA C6BA 171.33(13) . . . . ?
C5AA C5BA C7BA C0AA -4.2(2) . . . . ?
C5AA C5BA C3AA C4AA 162.78(13) . . . . ?
C5AA C5BA C3AA C9AA 43.4(2) . . . . ?
C5AA C5BA C3AA C0BA -76.28(18) . . . . ?
C6AA O2BA C8AA O4BA 40.23(14) . . . . ?
C6AA O2BA C8AA C21 -76.23(15) . . . . ?
C6AA O2BA C8AA C22 158.48(14) . . . . ?
C6AA C6BA C7BA C5BA -2.6(2) . . . . ?
C6AA C6BA C7BA C0AA 173.11(13) . . . . ?
C6AA C4AA C7AA C21 35.12(18) . . . . ?
C7AA C4AA C6AA O2BA -52.38(16) . . . . ?
C7AA C4AA C6AA C6BA 60.06(17) . . . . ?
C8AA O2BA C6AA C6BA -45.14(14) . . . . ?
C8AA O2BA C6AA C4AA 72.70(14) . . . . ?
C8AA O4BA C6BA C7BA -133.26(13) . . . . ?
C8AA O4BA C6BA C6AA -8.65(15) . . . . ?
C9AA C3AA C4AA C6AA 177.79(13) . . . . ?
C9AA C3AA C4AA C7AA 53.87(16) . . . . ?
C0BA C3AA C4AA C6AA -64.76(17) . . . . ?
C0BA C3AA C4AA C7AA 171.32(13) . . . . ?
C22 C8AA C21 C7AA -176.38(15) . . . . ?

_olex2_date_sample_data_collection 2019-12-04
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.553
_oxdiff_exptl_absorpt_empirical_full_min 0.537
####################################################################### 
# 
# 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_renpl_1025
_database_code_depnum_ccdc_archive 'CCDC 1997728'
loop_
_audit_author_name
_audit_author_address
'Panlong Ren'
;Lanzhou University
China
;
_audit_update_record             
;
2020-04-18 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_audit_creation_date             2019-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H26 O4'
_chemical_formula_sum            'C19 H26 O4'
_chemical_formula_weight         318.40
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.2175(5)
_cell_length_b                   13.7827(5)
_cell_length_c                   12.9330(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.529(5)
_cell_angle_gamma                90
_cell_volume                     1694.22(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2082
_cell_measurement_temperature    293.83(10)
_cell_measurement_theta_max      69.6930
_cell_measurement_theta_min      7.7630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5449
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        66.593
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         4.879
_diffrn_ambient_temperature      293.83(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  -30.0000 40

#__ type_ start__ end____ width___ exp.time_
  2 omega  -76.00  -42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -50.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
  3 omega  -28.00    4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -50.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -76.00  -51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega   32.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -30.0000 89

#__ type_ start__ end____ width___ exp.time_
  6 omega  -12.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega   24.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
  8 omega   43.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   63.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 31

#__ type_ start__ end____ width___ exp.time_
 10 omega   53.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 54

#__ type_ start__ end____ width___ exp.time_
 12 omega   41.00  132.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  150.0000 91

#__ type_ start__ end____ width___ exp.time_
 13 omega   36.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   92.0000 55

#__ type_ start__ end____ width___ exp.time_
 14 omega   46.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   90.0000 38

#__ type_ start__ end____ width___ exp.time_
 15 omega   43.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
 16 omega   82.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -120.0000 93
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0274455000
_diffrn_orient_matrix_UB_12      -0.0367787000
_diffrn_orient_matrix_UB_13      0.1027670000
_diffrn_orient_matrix_UB_21      -0.1596824000
_diffrn_orient_matrix_UB_22      0.0037534000
_diffrn_orient_matrix_UB_23      -0.0662694000
_diffrn_orient_matrix_UB_31      0.0038053000
_diffrn_orient_matrix_UB_32      -0.1054640000
_diffrn_orient_matrix_UB_33      -0.0381161000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2322
_reflns_number_total             2913
_reflns_odcompleteness_completeness 96.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2913
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.065
_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)+(0.0741P)²+0.3329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1469
_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:
 C2(H2), C3(H3), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C18(H18)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.48825(13) 0.04869(10) 0.30579(10) 0.0467(3) Uani 1 1 d . . . . .
C2 C 0.38011(18) 0.11092(13) 0.31443(14) 0.0408(4) Uani 1 1 d . . . . .
H2 H 0.314638 0.127027 0.239481 0.049 Uiso 1 1 calc R . . . .
C3 C 0.29966(19) 0.06346(13) 0.37738(14) 0.0412(4) Uani 1 1 d . . . . .
H3 H 0.364834 0.047812 0.452573 0.049 Uiso 1 1 calc R . . . .
C4 C 0.44819(19) 0.20307(13) 0.37246(14) 0.0424(4) Uani 1 1 d . . . . .
O5 O 0.14494(17) -0.01031(10) 0.20912(11) 0.0617(4) Uani 1 1 d . . . . .
H5 H 0.115709 -0.062036 0.177854 0.092 Uiso 1 1 calc GR . . . .
O6 O 0.63282(19) 0.17676(13) 0.29916(15) 0.0758(5) Uani 1 1 d . . . . .
C7 C 0.3977(2) 0.25561(13) 0.44365(14) 0.0442(4) Uani 1 1 d . . . . .
C8 C 0.4772(2) 0.33613(14) 0.49930(16) 0.0532(5) Uani 1 1 d . . . . .
C9 C 0.5723(2) 0.23035(15) 0.35939(16) 0.0517(5) Uani 1 1 d . . . . .
O10 O 0.43359(19) 0.38783(12) 0.57198(14) 0.0710(5) Uani 1 1 d . . . . .
H10 H 0.497303 0.423598 0.609804 0.106 Uiso 1 1 calc GR . . . .
C11 C 0.5621(2) 0.09119(16) 0.24393(16) 0.0505(5) Uani 1 1 d . . . . .
C12 C 0.1947(2) 0.13985(15) 0.38479(15) 0.0487(5) Uani 1 1 d . . . . .
H12 H 0.150684 0.167462 0.310146 0.058 Uiso 1 1 calc R . . . .
C13 C 0.2642(2) 0.22503(15) 0.46292(15) 0.0492(5) Uani 1 1 d . . . . .
C14 C 0.6454(2) 0.31219(17) 0.41230(19) 0.0610(6) Uani 1 1 d . . . . .
H14 H 0.726277 0.331660 0.400967 0.073 Uiso 1 1 calc R . . . .
C15 C 0.2100(2) -0.02620(14) 0.32713(14) 0.0463(4) Uani 1 1 d . . . . .
C16 C 0.1561(2) 0.30844(18) 0.4350(2) 0.0664(6) Uani 1 1 d . . . . .
H16A H 0.192238 0.360399 0.487192 0.100 Uiso 1 1 calc GR . . . .
H16B H 0.069616 0.285213 0.439317 0.100 Uiso 1 1 calc GR . . . .
H16C H 0.139003 0.331608 0.361209 0.100 Uiso 1 1 calc GR . . . .
C17 C 0.2900(2) -0.12037(15) 0.34791(17) 0.0605(6) Uani 1 1 d . . . . .
H17A H 0.361819 -0.117093 0.316683 0.091 Uiso 1 1 calc GR . . . .
H17B H 0.226560 -0.172536 0.313813 0.091 Uiso 1 1 calc GR . . . .
H17C H 0.332579 -0.131563 0.426500 0.091 Uiso 1 1 calc GR . . . .
C18 C 0.5970(2) 0.36423(15) 0.48173(18) 0.0602(6) Uani 1 1 d . . . . .
H18 H 0.645696 0.419159 0.517361 0.072 Uiso 1 1 calc R . . . .
C19 C 0.6762(3) 0.0219(2) 0.2461(2) 0.0777(7) Uani 1 1 d . . . . .
H19A H 0.733497 0.007070 0.321727 0.117 Uiso 1 1 calc GR . . . .
H19B H 0.733404 0.050991 0.209887 0.117 Uiso 1 1 calc GR . . . .
H19C H 0.634824 -0.036712 0.207929 0.117 Uiso 1 1 calc GR . . . .
C20 C 0.3059(3) 0.19505(18) 0.58649(17) 0.0642(6) Uani 1 1 d . . . . .
H20A H 0.358773 0.135747 0.599668 0.096 Uiso 1 1 calc GR . . . .
H20B H 0.222404 0.185609 0.602858 0.096 Uiso 1 1 calc GR . . . .
H20C H 0.362204 0.245235 0.633408 0.096 Uiso 1 1 calc GR . . . .
C21 C 0.0997(3) -0.0232(2) 0.3813(3) 0.0826(8) Uani 1 1 d . . . . .
H21A H 0.011424 -0.050006 0.331051 0.099 Uiso 1 1 calc R . . . .
H21B H 0.131049 -0.061455 0.448965 0.099 Uiso 1 1 calc R . . . .
C22 C 0.4681(3) 0.1175(3) 0.12718(19) 0.0878(10) Uani 1 1 d . . . . .
H22A H 0.412683 0.062178 0.091825 0.132 Uiso 1 1 calc GR . . . .
H22B H 0.524695 0.137509 0.085937 0.132 Uiso 1 1 calc GR . . . .
H22C H 0.406909 0.169723 0.129387 0.132 Uiso 1 1 calc GR . . . .
C23 C 0.0798(3) 0.0807(2) 0.4072(2) 0.0737(7) Uani 1 1 d . . . . .
H23A H 0.089175 0.087252 0.484251 0.088 Uiso 1 1 calc R . . . .
H23B H -0.012929 0.103302 0.360226 0.088 Uiso 1 1 calc R . . . .


_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 1.435(2) . ?
O1 C11 1.413(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.503(2) . ?
C2 C4 1.509(2) . ?
C3 H3 0.9800 . ?
C3 C12 1.531(3) . ?
C3 C15 1.533(2) . ?
C4 C7 1.410(3) . ?
C4 C9 1.391(3) . ?
O5 H5 0.8200 . ?
O5 C15 1.440(2) . ?
O6 C9 1.374(3) . ?
O6 C11 1.430(3) . ?
C7 C8 1.407(3) . ?
C7 C13 1.532(3) . ?
C8 O10 1.377(3) . ?
C8 C18 1.380(3) . ?
C9 C14 1.387(3) . ?
O10 H10 0.8200 . ?
C11 C19 1.500(3) . ?
C11 C22 1.507(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.542(3) . ?
C12 C23 1.542(3) . ?
C13 C16 1.543(3) . ?
C13 C20 1.551(3) . ?
C14 H14 0.9300 . ?
C14 C18 1.375(3) . ?
C15 C17 1.504(3) . ?
C15 C21 1.530(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C23 1.501(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C2 112.50(14) . . ?
O1 C2 H2 108.9 . . ?
O1 C2 C3 111.83(15) . . ?
O1 C2 C4 108.31(14) . . ?
C3 C2 H2 108.9 . . ?
C3 C2 C4 109.93(14) . . ?
C4 C2 H2 108.9 . . ?
C2 C3 H3 109.0 . . ?
C2 C3 C12 105.64(15) . . ?
C2 C3 C15 118.80(14) . . ?
C12 C3 H3 109.0 . . ?
C12 C3 C15 104.92(15) . . ?
C15 C3 H3 109.0 . . ?
C7 C4 C2 123.01(16) . . ?
C9 C4 C2 116.20(17) . . ?
C9 C4 C7 120.60(18) . . ?
C15 O5 H5 109.5 . . ?
C9 O6 C11 118.44(16) . . ?
C4 C7 C13 121.73(16) . . ?
C8 C7 C4 117.27(18) . . ?
C8 C7 C13 120.98(17) . . ?
O10 C8 C7 119.1(2) . . ?
O10 C8 C18 119.72(19) . . ?
C18 C8 C7 121.2(2) . . ?
O6 C9 C4 122.92(18) . . ?
O6 C9 C14 116.34(19) . . ?
C14 C9 C4 120.7(2) . . ?
C8 O10 H10 109.5 . . ?
O1 C11 O6 109.65(15) . . ?
O1 C11 C19 107.39(18) . . ?
O1 C11 C22 113.02(17) . . ?
O6 C11 C19 105.59(19) . . ?
O6 C11 C22 108.7(2) . . ?
C19 C11 C22 112.2(2) . . ?
C3 C12 H12 106.5 . . ?
C3 C12 C13 113.57(16) . . ?
C3 C12 C23 104.31(18) . . ?
C13 C12 H12 106.5 . . ?
C13 C12 C23 118.63(17) . . ?
C23 C12 H12 106.5 . . ?
C7 C13 C12 109.04(15) . . ?
C7 C13 C16 111.15(17) . . ?
C7 C13 C20 108.48(17) . . ?
C12 C13 C16 107.20(17) . . ?
C12 C13 C20 111.01(17) . . ?
C16 C13 C20 109.96(17) . . ?
C9 C14 H14 120.4 . . ?
C18 C14 C9 119.2(2) . . ?
C18 C14 H14 120.4 . . ?
O5 C15 C3 107.35(14) . . ?
O5 C15 C17 109.25(16) . . ?
O5 C15 C21 110.46(19) . . ?
C17 C15 C3 114.75(16) . . ?
C17 C15 C21 112.60(19) . . ?
C21 C15 C3 102.15(16) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 C18 H18 119.5 . . ?
C14 C18 C8 120.97(19) . . ?
C14 C18 H18 119.5 . . ?
C11 C19 H19A 109.5 . . ?
C11 C19 H19B 109.5 . . ?
C11 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C20 H20A 109.5 . . ?
C13 C20 H20B 109.5 . . ?
C13 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C21 H21A 110.1 . . ?
C15 C21 H21B 110.1 . . ?
H21A C21 H21B 108.4 . . ?
C23 C21 C15 108.08(19) . . ?
C23 C21 H21A 110.1 . . ?
C23 C21 H21B 110.1 . . ?
C11 C22 H22A 109.5 . . ?
C11 C22 H22B 109.5 . . ?
C11 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C12 C23 H23A 110.4 . . ?
C12 C23 H23B 110.4 . . ?
C21 C23 C12 106.72(18) . . ?
C21 C23 H23A 110.4 . . ?
C21 C23 H23B 110.4 . . ?
H23A C23 H23B 108.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C12 177.11(13) . . . . ?
O1 C2 C3 C15 -65.6(2) . . . . ?
O1 C2 C4 C7 -146.45(16) . . . . ?
O1 C2 C4 C9 28.5(2) . . . . ?
C2 O1 C11 O6 62.8(2) . . . . ?
C2 O1 C11 C19 177.05(16) . . . . ?
C2 O1 C11 C22 -58.7(2) . . . . ?
C2 C3 C12 C13 -70.39(19) . . . . ?
C2 C3 C12 C23 159.00(16) . . . . ?
C2 C3 C15 O5 -38.7(2) . . . . ?
C2 C3 C15 C17 82.9(2) . . . . ?
C2 C3 C15 C21 -155.0(2) . . . . ?
C2 C4 C7 C8 175.17(16) . . . . ?
C2 C4 C7 C13 -3.0(3) . . . . ?
C2 C4 C9 O6 -1.1(3) . . . . ?
C2 C4 C9 C14 -177.90(17) . . . . ?
C3 C2 C4 C7 -24.0(2) . . . . ?
C3 C2 C4 C9 150.94(17) . . . . ?
C3 C12 C13 C7 42.7(2) . . . . ?
C3 C12 C13 C16 163.10(16) . . . . ?
C3 C12 C13 C20 -76.8(2) . . . . ?
C3 C12 C23 C21 -15.0(3) . . . . ?
C3 C15 C21 C23 28.1(3) . . . . ?
C4 C2 C3 C12 56.75(18) . . . . ?
C4 C2 C3 C15 174.08(15) . . . . ?
C4 C7 C8 O10 -178.22(17) . . . . ?
C4 C7 C8 C18 2.2(3) . . . . ?
C4 C7 C13 C12 -6.0(2) . . . . ?
C4 C7 C13 C16 -123.93(19) . . . . ?
C4 C7 C13 C20 115.06(19) . . . . ?
C4 C9 C14 C18 2.6(3) . . . . ?
O5 C15 C21 C23 -85.8(2) . . . . ?
O6 C9 C14 C18 -174.4(2) . . . . ?
C7 C4 C9 O6 173.93(18) . . . . ?
C7 C4 C9 C14 -2.8(3) . . . . ?
C7 C8 C18 C14 -2.4(3) . . . . ?
C8 C7 C13 C12 175.93(16) . . . . ?
C8 C7 C13 C16 58.0(2) . . . . ?
C8 C7 C13 C20 -63.1(2) . . . . ?
C9 C4 C7 C8 0.4(3) . . . . ?
C9 C4 C7 C13 -177.73(17) . . . . ?
C9 O6 C11 O1 -31.9(3) . . . . ?
C9 O6 C11 C19 -147.3(2) . . . . ?
C9 O6 C11 C22 92.2(2) . . . . ?
C9 C14 C18 C8 0.0(3) . . . . ?
O10 C8 C18 C14 177.95(19) . . . . ?
C11 O1 C2 C3 178.22(14) . . . . ?
C11 O1 C2 C4 -60.49(18) . . . . ?
C11 O6 C9 C4 2.5(3) . . . . ?
C11 O6 C9 C14 179.42(19) . . . . ?
C12 C3 C15 O5 78.96(18) . . . . ?
C12 C3 C15 C17 -159.41(16) . . . . ?
C12 C3 C15 C21 -37.3(2) . . . . ?
C13 C7 C8 O10 0.0(3) . . . . ?
C13 C7 C8 C18 -179.65(18) . . . . ?
C13 C12 C23 C21 -142.5(2) . . . . ?
C15 C3 C12 C13 163.29(15) . . . . ?
C15 C3 C12 C23 32.68(19) . . . . ?
C15 C21 C23 C12 -8.4(3) . . . . ?
C17 C15 C21 C23 151.7(2) . . . . ?
C23 C12 C13 C7 165.73(19) . . . . ?
C23 C12 C13 C16 -73.8(2) . . . . ?
C23 C12 C13 C20 46.3(3) . . . . ?

_olex2_date_sample_data_collection 2019-10-25
_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_tangt_0107
_database_code_depnum_ccdc_archive 'CCDC 1997731'
loop_
_audit_author_name
_audit_author_address
'Panlong Ren'
;Lanzhou University
China
;
_audit_update_record             
;
2020-04-18 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_audit_creation_date             2019-05-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H22 O4'
_chemical_formula_sum            'C16 H22 O4'
_chemical_formula_weight         278.33
_chemical_absolute_configuration unk
_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.3946(2)
_cell_length_b                   11.4810(3)
_cell_length_c                   15.2872(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1473.35(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2251
_cell_measurement_temperature    292.64(10)
_cell_measurement_theta_max      69.7020
_cell_measurement_theta_min      7.1230
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.881
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4707
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        66.582
_diffrn_reflns_theta_max         66.582
_diffrn_reflns_theta_min         4.817
_diffrn_ambient_temperature      292.64(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -22.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega  -74.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega  -73.00  -42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  150.0000 31

#__ type_ start__ end____ width___ exp.time_
  4 omega  -68.00  -40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega  -64.00  -24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  125.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
  6 omega   40.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
  7 omega   89.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   29.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000    4.8064 47

#__ type_ start__ end____ width___ exp.time_
  9 omega   49.00   75.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   44.00  128.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   90.0000 84

#__ type_ start__ end____ width___ exp.time_
 11 omega   76.00  110.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
 12 omega   46.00   72.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega  127.00  176.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000 -150.0000 49

#__ type_ start__ end____ width___ exp.time_
 14 omega   38.00   85.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
 15 omega   45.00   93.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
 16 omega   36.00   83.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 47

#__ type_ start__ end____ width___ exp.time_
 17 omega   37.00   90.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
 18 omega   45.00   93.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
 19 omega   37.00   70.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 33
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0436449000
_diffrn_orient_matrix_UB_12      0.1066294000
_diffrn_orient_matrix_UB_13      0.0562846000
_diffrn_orient_matrix_UB_21      -0.0257804000
_diffrn_orient_matrix_UB_22      0.0800031000
_diffrn_orient_matrix_UB_23      -0.0796391000
_diffrn_orient_matrix_UB_31      -0.1763942000
_diffrn_orient_matrix_UB_32      0.0146770000
_diffrn_orient_matrix_UB_33      0.0255845000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    0.943
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                2297
_reflns_number_total             2480
_reflns_odcompleteness_completeness 96.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 
;
 Flack x determined using 889 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.14(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2480
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.053
_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)+(0.0354P)²+0.0658P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0718
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5509(2) -0.18982(15) 0.88509(11) 0.0559(5) Uani 1 1 d . . . . .
H1 H 0.610733 -0.226927 0.853156 0.084 Uiso 1 1 calc GR . . . .
O2 O 0.24709(18) 0.16493(12) 0.70690(9) 0.0353(3) Uani 1 1 d . . . . .
O3 O 0.17005(17) 0.10844(13) 0.97964(9) 0.0358(3) Uani 1 1 d . . . . .
H3 H 0.250074 0.136314 1.002187 0.054 Uiso 1 1 calc GR . . . .
O4 O -0.08564(19) 0.25734(13) 0.95892(10) 0.0430(4) Uani 1 1 d . . . . .
H4 H -0.008680 0.240931 0.989565 0.065 Uiso 1 1 calc GR . . . .
C1 C 0.3222(2) 0.07461(16) 0.75195(14) 0.0313(4) Uani 1 1 d . . . . .
C2 C 0.4330(3) 0.00719(19) 0.70815(15) 0.0397(5) Uani 1 1 d . . . . .
H2 H 0.453540 0.021389 0.649324 0.048 Uiso 1 1 calc R . . . .
C3 C 0.5140(3) -0.08142(19) 0.75102(16) 0.0408(5) Uani 1 1 d . . . . .
H3A H 0.589665 -0.125771 0.721616 0.049 Uiso 1 1 calc R . . . .
C4 C 0.4804(3) -0.10277(18) 0.83819(15) 0.0377(5) Uani 1 1 d . . . . .
C5 C 0.3707(2) -0.03404(18) 0.88246(14) 0.0348(5) Uani 1 1 d . . . . .
H5 H 0.350321 -0.048365 0.941278 0.042 Uiso 1 1 calc R . . . .
C6 C 0.2912(2) 0.05559(16) 0.84028(13) 0.0292(4) Uani 1 1 d . . . . .
C7 C 0.1717(2) 0.13130(15) 0.88785(12) 0.0278(4) Uani 1 1 d . . . . .
H7 H 0.202468 0.212844 0.879253 0.033 Uiso 1 1 calc R . . . .
C8 C 0.0036(2) 0.11484(16) 0.85048(12) 0.0267(4) Uani 1 1 d . . . . .
H8 H -0.011472 0.032028 0.837331 0.032 Uiso 1 1 calc R . . . .
C9 C -0.1351(2) 0.15533(18) 0.91033(14) 0.0326(4) Uani 1 1 d . . . . .
C10 C -0.2666(3) 0.1952(2) 0.84697(16) 0.0440(5) Uani 1 1 d . . . . .
H10A H -0.361616 0.148367 0.854906 0.053 Uiso 1 1 calc R . . . .
H10B H -0.293602 0.276126 0.857749 0.053 Uiso 1 1 calc R . . . .
C11 C -0.2024(3) 0.1806(2) 0.75442(15) 0.0474(6) Uani 1 1 d . . . . .
H11A H -0.238595 0.243337 0.716835 0.057 Uiso 1 1 calc R . . . .
H11B H -0.235910 0.106865 0.729554 0.057 Uiso 1 1 calc R . . . .
C12 C -0.0211(2) 0.18442(17) 0.76584(13) 0.0312(4) Uani 1 1 d . . . . .
H12 H 0.006664 0.265415 0.779177 0.037 Uiso 1 1 calc R . . . .
C13 C 0.0757(3) 0.15006(18) 0.68534(13) 0.0338(4) Uani 1 1 d . . . . .
C14 C 0.0455(3) 0.0270(2) 0.65331(16) 0.0443(5) Uani 1 1 d . . . . .
H14A H 0.120886 0.007963 0.608282 0.066 Uiso 1 1 calc GR . . . .
H14B H -0.060572 0.021631 0.630239 0.066 Uiso 1 1 calc GR . . . .
H14C H 0.057190 -0.026529 0.701135 0.066 Uiso 1 1 calc GR . . . .
C15 C 0.0498(3) 0.2380(2) 0.61181(16) 0.0527(6) Uani 1 1 d . . . . .
H15A H 0.073352 0.314924 0.632771 0.079 Uiso 1 1 calc GR . . . .
H15B H -0.059100 0.234746 0.592769 0.079 Uiso 1 1 calc GR . . . .
H15C H 0.118778 0.219664 0.563665 0.079 Uiso 1 1 calc GR . . . .
C16 C -0.1933(3) 0.0621(2) 0.97352(17) 0.0499(6) Uani 1 1 d . . . . .
H16A H -0.104956 0.033336 1.007052 0.075 Uiso 1 1 calc GR . . . .
H16B H -0.240203 -0.000775 0.941142 0.075 Uiso 1 1 calc GR . . . .
H16C H -0.271310 0.095002 1.012207 0.075 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C4 1.365(3) . ?
O2 C1 1.395(2) . ?
O2 C13 1.486(2) . ?
O3 H3 0.8200 . ?
O3 C7 1.428(2) . ?
O4 H4 0.8200 . ?
O4 C9 1.448(2) . ?
C1 C2 1.383(3) . ?
C1 C6 1.392(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(3) . ?
C3 H3A 0.9300 . ?
C3 C4 1.384(3) . ?
C4 C5 1.389(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(3) . ?
C6 C7 1.513(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.534(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.552(3) . ?
C8 C12 1.535(3) . ?
C9 C10 1.538(3) . ?
C9 C16 1.522(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.523(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.533(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.527(3) . ?
C13 C14 1.517(3) . ?
C13 C15 1.527(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C4 O1 H1 109.5 . . ?
C1 O2 C13 117.50(15) . . ?
C7 O3 H3 109.5 . . ?
C9 O4 H4 109.5 . . ?
C2 C1 O2 118.75(19) . . ?
C2 C1 C6 120.50(19) . . ?
C6 C1 O2 120.70(17) . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 C2 119.0(2) . . ?
C4 C3 H3A 120.5 . . ?
O1 C4 C3 123.18(19) . . ?
O1 C4 C5 116.59(19) . . ?
C3 C4 C5 120.2(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 120.00(17) . . ?
C5 C6 C1 118.52(18) . . ?
C5 C6 C7 121.48(18) . . ?
O3 C7 C6 111.92(16) . . ?
O3 C7 H7 108.1 . . ?
O3 C7 C8 109.53(16) . . ?
C6 C7 H7 108.1 . . ?
C6 C7 C8 111.09(15) . . ?
C8 C7 H7 108.1 . . ?
C7 C8 H8 108.3 . . ?
C7 C8 C9 115.71(15) . . ?
C7 C8 C12 111.95(16) . . ?
C9 C8 H8 108.3 . . ?
C12 C8 H8 108.3 . . ?
C12 C8 C9 103.88(16) . . ?
O4 C9 C8 109.23(16) . . ?
O4 C9 C10 106.73(17) . . ?
O4 C9 C16 109.59(19) . . ?
C10 C9 C8 104.85(17) . . ?
C16 C9 C8 113.83(18) . . ?
C16 C9 C10 112.28(18) . . ?
C9 C10 H10A 110.2 . . ?
C9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C11 C10 C9 107.36(18) . . ?
C11 C10 H10A 110.2 . . ?
C11 C10 H10B 110.2 . . ?
C10 C11 H11A 111.0 . . ?
C10 C11 H11B 111.0 . . ?
C10 C11 C12 104.03(18) . . ?
H11A C11 H11B 109.0 . . ?
C12 C11 H11A 111.0 . . ?
C12 C11 H11B 111.0 . . ?
C8 C12 H12 106.6 . . ?
C11 C12 C8 102.43(17) . . ?
C11 C12 H12 106.6 . . ?
C13 C12 C8 118.25(17) . . ?
C13 C12 C11 115.43(18) . . ?
C13 C12 H12 106.6 . . ?
O2 C13 C12 107.87(16) . . ?
O2 C13 C14 109.91(17) . . ?
O2 C13 C15 103.03(18) . . ?
C12 C13 C15 110.28(18) . . ?
C14 C13 C12 114.34(18) . . ?
C14 C13 C15 110.77(19) . . ?
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 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C4 C5 C6 -179.13(19) . . . . ?
O2 C1 C2 C3 178.15(18) . . . . ?
O2 C1 C6 C5 -178.97(17) . . . . ?
O2 C1 C6 C7 1.6(3) . . . . ?
O3 C7 C8 C9 37.2(2) . . . . ?
O3 C7 C8 C12 155.92(15) . . . . ?
O4 C9 C10 C11 114.4(2) . . . . ?
C1 O2 C13 C12 82.7(2) . . . . ?
C1 O2 C13 C14 -42.5(2) . . . . ?
C1 O2 C13 C15 -160.63(17) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C1 C6 C7 O3 -172.84(16) . . . . ?
C1 C6 C7 C8 64.4(2) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
C2 C1 C6 C7 178.94(18) . . . . ?
C2 C3 C4 O1 178.3(2) . . . . ?
C2 C3 C4 C5 -1.9(3) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 C7 -179.82(18) . . . . ?
C5 C6 C7 O3 7.7(3) . . . . ?
C5 C6 C7 C8 -115.1(2) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C6 C7 C8 C9 161.31(16) . . . . ?
C6 C7 C8 C12 -79.9(2) . . . . ?
C7 C8 C9 O4 34.9(2) . . . . ?
C7 C8 C9 C10 149.00(17) . . . . ?
C7 C8 C9 C16 -87.9(2) . . . . ?
C7 C8 C12 C11 -166.04(16) . . . . ?
C7 C8 C12 C13 65.8(2) . . . . ?
C8 C9 C10 C11 -1.4(2) . . . . ?
C8 C12 C13 O2 -61.3(2) . . . . ?
C8 C12 C13 C14 61.3(2) . . . . ?
C8 C12 C13 C15 -173.09(19) . . . . ?
C9 C8 C12 C11 -40.5(2) . . . . ?
C9 C8 C12 C13 -168.63(17) . . . . ?
C9 C10 C11 C12 -23.7(2) . . . . ?
C10 C11 C12 C8 39.6(2) . . . . ?
C10 C11 C12 C13 169.49(18) . . . . ?
C11 C12 C13 O2 177.00(18) . . . . ?
C11 C12 C13 C14 -60.4(3) . . . . ?
C11 C12 C13 C15 65.2(3) . . . . ?
C12 C8 C9 O4 -88.20(19) . . . . ?
C12 C8 C9 C10 25.9(2) . . . . ?
C12 C8 C9 C16 148.96(18) . . . . ?
C13 O2 C1 C2 109.3(2) . . . . ?
C13 O2 C1 C6 -73.2(2) . . . . ?
C16 C9 C10 C11 -125.5(2) . . . . ?

_olex2_date_sample_data_collection 2019-01-07
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tangt_k1b_9_3_3_6
_database_code_depnum_ccdc_archive 'CCDC 1997729'
loop_
_audit_author_name
_audit_author_address
'Panlong Ren'
;Lanzhou University
China
;
_audit_update_record             
;
2020-04-18 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_audit_creation_date             2018-11-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H24 O4'
_chemical_formula_sum            'C17 H24 O4'
_chemical_formula_weight         292.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   27.5479(8)
_cell_length_b                   6.3331(2)
_cell_length_c                   18.4336(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.280(3)
_cell_angle_gamma                90
_cell_volume                     3215.22(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4993
_cell_measurement_temperature    292.10(10)
_cell_measurement_theta_max      69.6200
_cell_measurement_theta_min      7.1430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13038
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         4.799
_diffrn_ambient_temperature      292.10(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -47.00   25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   25.0000  -30.0000 72

#__ type_ start__ end____ width___ exp.time_
  2 omega  -55.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -50.0000  -30.0000 47

#__ type_ start__ end____ width___ exp.time_
  3 omega   -5.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   38.0000    0.0000 69

#__ type_ start__ end____ width___ exp.time_
  4 omega   33.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 72

#__ type_ start__ end____ width___ exp.time_
  5 omega   27.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
  6 omega   40.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   30.0000 80

#__ type_ start__ end____ width___ exp.time_
  7 omega   28.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
  8 omega  -14.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -60.0000 79

#__ type_ start__ end____ width___ exp.time_
  9 omega   81.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   85.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
 11 omega  118.00  144.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   86.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000    0.0000 63

#__ type_ start__ end____ width___ exp.time_
 13 omega   86.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   85.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
 15 omega  100.00  170.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 70

#__ type_ start__ end____ width___ exp.time_
 16 omega   76.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   81.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   76.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   76.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   89.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -108.0000  -56.0000 25

#__ type_ start__ end____ width___ exp.time_
 21 omega   76.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega   82.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
 23 omega   84.00  168.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
 24 omega   35.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 80

#__ type_ start__ end____ width___ exp.time_
 25 omega   77.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 26 omega   75.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 27 omega  110.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 66

#__ type_ start__ end____ width___ exp.time_
 28 omega  131.00  170.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 39

#__ type_ start__ end____ width___ exp.time_
 29 omega   81.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   81.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
 31 omega   85.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 32 omega   84.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 33 omega   76.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   54.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
 35 omega   82.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 36 omega   75.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 37 omega  112.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 51

#__ type_ start__ end____ width___ exp.time_
 38 omega   89.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 39 omega  106.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 72

#__ type_ start__ end____ width___ exp.time_
 40 omega   62.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 41 omega  153.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    8.0373 25

#__ type_ start__ end____ width___ exp.time_
 42 omega   82.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 43 omega   76.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 44 omega  114.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 45 omega   76.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 46 omega   76.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    8.0373 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0538204000
_diffrn_orient_matrix_UB_12      0.0596967000
_diffrn_orient_matrix_UB_13      0.0080524000
_diffrn_orient_matrix_UB_21      0.0080064000
_diffrn_orient_matrix_UB_22      0.0208226000
_diffrn_orient_matrix_UB_23      0.0826850000
_diffrn_orient_matrix_UB_31      0.0129994000
_diffrn_orient_matrix_UB_32      0.2348410000
_diffrn_orient_matrix_UB_33      -0.0093870000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2491
_reflns_number_total             2807
_reflns_odcompleteness_completeness 98.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2807
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.057
_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)+(0.0581P)²+1.2866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1114
_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:
 C6(H6), C10(H10), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C1AA(H1AA,H1AB,H1AC), C2AA(H2AA,H2AB,H2AC), C0AA(H0AA,
 H0AB,H0AC)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.23646(3) 0.04469(18) 0.60025(5) 0.0478(3) Uani 1 1 d . . . . .
H1 H 0.244061 0.105624 0.562930 0.072 Uiso 1 1 calc GR . . . .
O2 O 0.28797(3) 0.36140(15) 0.54156(5) 0.0428(2) Uani 1 1 d . . . . .
O3 O 0.36042(3) 0.27557(18) 0.41241(5) 0.0480(3) Uani 1 1 d . . . . .
H3 H 0.334748 0.340067 0.407491 0.072 Uiso 1 1 calc GR . . . .
O4 O 0.39045(4) -0.0381(3) 0.79401(6) 0.0750(4) Uani 1 1 d . . . . .
H4 H 0.381515 -0.109955 0.828223 0.113 Uiso 1 1 calc GR . . . .
C5 C 0.27633(5) 0.0319(2) 0.64665(7) 0.0379(3) Uani 1 1 d . . . . .
C6 C 0.32711(4) 0.2135(2) 0.55467(6) 0.0342(3) Uani 1 1 d . . . . .
H6 H 0.323892 0.103591 0.517460 0.041 Uiso 1 1 calc R . . . .
C7 C 0.30688(6) -0.0851(3) 0.76094(8) 0.0538(4) Uani 1 1 d . . . . .
H7 H 0.301626 -0.146023 0.805998 0.065 Uiso 1 1 calc R . . . .
C8 C 0.32251(5) 0.1040(2) 0.62787(6) 0.0356(3) Uani 1 1 d . . . . .
C9 C 0.39039(5) 0.3779(2) 0.46654(7) 0.0447(3) Uani 1 1 d . . . . .
C10 C 0.37618(5) 0.3139(2) 0.54546(6) 0.0374(3) Uani 1 1 d . . . . .
H10 H 0.377875 0.440485 0.575992 0.045 Uiso 1 1 calc R . . . .
C11 C 0.26857(5) -0.0624(2) 0.71243(8) 0.0471(3) Uani 1 1 d . . . . .
H11 H 0.237798 -0.110421 0.724051 0.056 Uiso 1 1 calc R . . . .
C12 C 0.35307(6) -0.0189(3) 0.74384(8) 0.0509(4) Uani 1 1 d . . . . .
C13 C 0.36264(5) 0.0698(2) 0.67574(7) 0.0412(3) Uani 1 1 d . . . . .
C14 C 0.41513(5) 0.1229(3) 0.65434(8) 0.0482(4) Uani 1 1 d . . . . .
C15 C 0.41517(5) 0.1612(2) 0.57201(7) 0.0433(3) Uani 1 1 d . . . . .
H15 H 0.408083 0.025106 0.548826 0.052 Uiso 1 1 calc R . . . .
C16 C 0.44187(5) 0.2874(3) 0.45904(9) 0.0604(4) Uani 1 1 d . . . . .
H16A H 0.440970 0.156593 0.431658 0.073 Uiso 1 1 calc R . . . .
H16B H 0.462564 0.387106 0.434442 0.073 Uiso 1 1 calc R . . . .
C17 C 0.46067(5) 0.2483(3) 0.53644(9) 0.0594(4) Uani 1 1 d . . . . .
H17A H 0.471598 0.378058 0.559473 0.071 Uiso 1 1 calc R . . . .
H17B H 0.486907 0.146097 0.537668 0.071 Uiso 1 1 calc R . . . .
C18 C 0.43282(7) 0.3161(3) 0.69782(9) 0.0699(5) Uani 1 1 d . . . . .
H18A H 0.412215 0.434615 0.686815 0.105 Uiso 1 1 calc GR . . . .
H18B H 0.465561 0.348879 0.685050 0.105 Uiso 1 1 calc GR . . . .
H18C H 0.431737 0.285503 0.748764 0.105 Uiso 1 1 calc GR . . . .
C1AA C 0.28510(6) 0.5343(3) 0.59095(9) 0.0575(4) Uani 1 1 d . . . . .
H1AA H 0.310131 0.634836 0.580736 0.086 Uiso 1 1 calc GR . . . .
H1AB H 0.289329 0.483560 0.639753 0.086 Uiso 1 1 calc GR . . . .
H1AC H 0.253925 0.600931 0.585576 0.086 Uiso 1 1 calc GR . . . .
C2AA C 0.38814(8) 0.6135(3) 0.45486(10) 0.0738(6) Uani 1 1 d . . . . .
H2AA H 0.396919 0.645631 0.405972 0.111 Uiso 1 1 calc GR . . . .
H2AB H 0.410327 0.682161 0.488113 0.111 Uiso 1 1 calc GR . . . .
H2AC H 0.355757 0.662609 0.463048 0.111 Uiso 1 1 calc GR . . . .
C0AA C 0.44957(6) -0.0652(4) 0.66877(11) 0.0744(6) Uani 1 1 d . . . . .
H0AA H 0.451167 -0.094522 0.719856 0.112 Uiso 1 1 calc GR . . . .
H0AB H 0.481409 -0.030838 0.652220 0.112 Uiso 1 1 calc GR . . . .
H0AC H 0.437567 -0.187176 0.643203 0.112 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C5 1.3792(15) . ?
O2 C6 1.4443(15) . ?
O2 C1AA 1.4276(18) . ?
O3 H3 0.8200 . ?
O3 C9 1.4354(16) . ?
O4 H4 0.8200 . ?
O4 C12 1.3740(17) . ?
C5 C8 1.4022(18) . ?
C5 C11 1.3728(19) . ?
C6 H6 0.9800 . ?
C6 C8 1.5250(16) . ?
C6 C10 1.5070(17) . ?
C7 H7 0.9300 . ?
C7 C11 1.375(2) . ?
C7 C12 1.383(2) . ?
C8 C13 1.4157(18) . ?
C9 C10 1.5682(17) . ?
C9 C16 1.539(2) . ?
C9 C2AA 1.509(2) . ?
C10 H10 0.9800 . ?
C10 C15 1.5179(19) . ?
C11 H11 0.9300 . ?
C12 C13 1.406(2) . ?
C13 C14 1.5444(19) . ?
C14 C15 1.5370(19) . ?
C14 C18 1.536(2) . ?
C14 C0AA 1.542(2) . ?
C15 H15 0.9800 . ?
C15 C17 1.5301(19) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.527(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C1AA H1AA 0.9600 . ?
C1AA H1AB 0.9600 . ?
C1AA H1AC 0.9600 . ?
C2AA H2AA 0.9600 . ?
C2AA H2AB 0.9600 . ?
C2AA H2AC 0.9600 . ?
C0AA H0AA 0.9600 . ?
C0AA H0AB 0.9600 . ?
C0AA H0AC 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 H1 109.5 . . ?
C1AA O2 C6 116.26(10) . . ?
C9 O3 H3 109.5 . . ?
C12 O4 H4 109.5 . . ?
O1 C5 C8 122.82(11) . . ?
C11 C5 O1 115.84(12) . . ?
C11 C5 C8 121.31(12) . . ?
O2 C6 H6 106.7 . . ?
O2 C6 C8 111.51(10) . . ?
O2 C6 C10 112.07(10) . . ?
C8 C6 H6 106.7 . . ?
C10 C6 H6 106.7 . . ?
C10 C6 C8 112.59(10) . . ?
C11 C7 H7 119.4 . . ?
C11 C7 C12 121.11(13) . . ?
C12 C7 H7 119.4 . . ?
C5 C8 C6 117.41(11) . . ?
C5 C8 C13 119.77(11) . . ?
C13 C8 C6 122.81(11) . . ?
O3 C9 C10 112.13(11) . . ?
O3 C9 C16 106.64(12) . . ?
O3 C9 C2AA 109.03(14) . . ?
C16 C9 C10 103.70(12) . . ?
C2AA C9 C10 112.19(13) . . ?
C2AA C9 C16 112.99(14) . . ?
C6 C10 C9 117.17(10) . . ?
C6 C10 H10 108.2 . . ?
C6 C10 C15 108.97(11) . . ?
C9 C10 H10 108.2 . . ?
C15 C10 C9 105.91(11) . . ?
C15 C10 H10 108.2 . . ?
C5 C11 C7 119.17(13) . . ?
C5 C11 H11 120.4 . . ?
C7 C11 H11 120.4 . . ?
O4 C12 C7 119.96(13) . . ?
O4 C12 C13 118.94(13) . . ?
C7 C12 C13 121.10(13) . . ?
C8 C13 C14 122.01(12) . . ?
C12 C13 C8 117.29(12) . . ?
C12 C13 C14 120.70(12) . . ?
C15 C14 C13 107.94(11) . . ?
C15 C14 C0AA 106.15(14) . . ?
C18 C14 C13 109.17(13) . . ?
C18 C14 C15 112.47(13) . . ?
C18 C14 C0AA 109.78(14) . . ?
C0AA C14 C13 111.31(13) . . ?
C10 C15 C14 113.75(12) . . ?
C10 C15 H15 106.7 . . ?
C10 C15 C17 102.30(12) . . ?
C14 C15 H15 106.7 . . ?
C17 C15 C14 119.91(12) . . ?
C17 C15 H15 106.7 . . ?
C9 C16 H16A 110.6 . . ?
C9 C16 H16B 110.6 . . ?
H16A C16 H16B 108.7 . . ?
C17 C16 C9 105.69(13) . . ?
C17 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
C15 C17 H17A 111.5 . . ?
C15 C17 H17B 111.5 . . ?
C16 C17 C15 101.24(12) . . ?
C16 C17 H17A 111.5 . . ?
C16 C17 H17B 111.5 . . ?
H17A C17 H17B 109.3 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C1AA H1AA 109.5 . . ?
O2 C1AA H1AB 109.5 . . ?
O2 C1AA H1AC 109.5 . . ?
H1AA C1AA H1AB 109.5 . . ?
H1AA C1AA H1AC 109.5 . . ?
H1AB C1AA H1AC 109.5 . . ?
C9 C2AA H2AA 109.5 . . ?
C9 C2AA H2AB 109.5 . . ?
C9 C2AA H2AC 109.5 . . ?
H2AA C2AA H2AB 109.5 . . ?
H2AA C2AA H2AC 109.5 . . ?
H2AB C2AA H2AC 109.5 . . ?
C14 C0AA H0AA 109.5 . . ?
C14 C0AA H0AB 109.5 . . ?
C14 C0AA H0AC 109.5 . . ?
H0AA C0AA H0AB 109.5 . . ?
H0AA C0AA H0AC 109.5 . . ?
H0AB C0AA H0AC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C5 C8 C6 4.10(19) . . . . ?
O1 C5 C8 C13 -174.68(12) . . . . ?
O1 C5 C11 C7 178.58(14) . . . . ?
O2 C6 C8 C5 43.98(15) . . . . ?
O2 C6 C8 C13 -137.27(12) . . . . ?
O2 C6 C10 C9 -69.14(14) . . . . ?
O2 C6 C10 C15 170.71(10) . . . . ?
O3 C9 C10 C6 -17.12(18) . . . . ?
O3 C9 C10 C15 104.64(13) . . . . ?
O3 C9 C16 C17 -137.18(13) . . . . ?
O4 C12 C13 C8 -174.62(15) . . . . ?
O4 C12 C13 C14 6.5(2) . . . . ?
C5 C8 C13 C12 -5.9(2) . . . . ?
C5 C8 C13 C14 173.01(13) . . . . ?
C6 C8 C13 C12 175.41(13) . . . . ?
C6 C8 C13 C14 -5.7(2) . . . . ?
C6 C10 C15 C14 -67.64(14) . . . . ?
C6 C10 C15 C17 161.55(11) . . . . ?
C7 C12 C13 C8 5.0(2) . . . . ?
C7 C12 C13 C14 -173.93(15) . . . . ?
C8 C5 C11 C7 0.5(2) . . . . ?
C8 C6 C10 C9 164.19(11) . . . . ?
C8 C6 C10 C15 44.04(14) . . . . ?
C8 C13 C14 C15 -13.32(19) . . . . ?
C8 C13 C14 C18 109.22(15) . . . . ?
C8 C13 C14 C0AA -129.43(15) . . . . ?
C9 C10 C15 C14 165.48(11) . . . . ?
C9 C10 C15 C17 34.67(14) . . . . ?
C9 C16 C17 C15 40.08(18) . . . . ?
C10 C6 C8 C5 170.95(11) . . . . ?
C10 C6 C8 C13 -10.30(17) . . . . ?
C10 C9 C16 C17 -18.66(16) . . . . ?
C10 C15 C17 C16 -45.75(16) . . . . ?
C11 C5 C8 C6 -177.91(13) . . . . ?
C11 C5 C8 C13 3.3(2) . . . . ?
C11 C7 C12 O4 178.23(16) . . . . ?
C11 C7 C12 C13 -1.4(3) . . . . ?
C12 C7 C11 C5 -1.5(3) . . . . ?
C12 C13 C14 C15 165.52(14) . . . . ?
C12 C13 C14 C18 -71.94(19) . . . . ?
C12 C13 C14 C0AA 49.4(2) . . . . ?
C13 C14 C15 C10 49.76(16) . . . . ?
C13 C14 C15 C17 171.19(14) . . . . ?
C14 C15 C17 C16 -172.69(15) . . . . ?
C16 C9 C10 C6 -131.78(13) . . . . ?
C16 C9 C10 C15 -10.02(14) . . . . ?
C18 C14 C15 C10 -70.74(17) . . . . ?
C18 C14 C15 C17 50.7(2) . . . . ?
C1AA O2 C6 C8 62.57(15) . . . . ?
C1AA O2 C6 C10 -64.68(14) . . . . ?
C2AA C9 C10 C6 105.98(16) . . . . ?
C2AA C9 C10 C15 -132.27(15) . . . . ?
C2AA C9 C16 C17 103.06(16) . . . . ?
C0AA C14 C15 C10 169.19(13) . . . . ?
C0AA C14 C15 C17 -69.37(19) . . . . ?

_olex2_date_sample_data_collection 2018-11-29
_olex2_submission_special_instructions 'No special instructions were received'
