# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_pm02as230519
_database_code_depnum_ccdc_archive 'CCDC 2094087'
loop_
_audit_author_name
_audit_author_address
'Saranphong Yimklan'
;Department of Chemistry, Faculty of Science, Chiang Mai University
Thailand
;
_audit_update_record             
;
2021-07-02 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;
_audit_creation_date             2021-07-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H26 O4'
_chemical_formula_sum            'C24 H26 O4'
_chemical_formula_weight         378.45
_chemical_absolute_configuration rm
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.0685(3)
_cell_length_b                   10.1743(3)
_cell_length_c                   20.3368(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2083.30(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8934
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9420
_cell_measurement_theta_min      2.2370
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.207
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16394
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.426
_diffrn_reflns_theta_min         2.238
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00   3.00   0.50    8.00    --   -9.67 -42.00  -1.00  150
  2  ω    -44.00  36.00   0.50    8.00    --   10.38 -79.00-156.00  160
  3  ω    -21.00  54.00   0.50    8.00    --   -9.67  37.00 -60.00  150
  4  ω    -56.00  -9.00   0.50    8.00    --   -9.67 125.00  30.00   94
  5  ω    -47.00 -19.00   0.50    8.00    --   -9.67 124.00-147.00   56
  6  ω    -51.00  -7.00   0.50    8.00    --   -9.67 -57.00 150.00   88
  7  ω    -52.00  22.00   0.50    8.00    --   10.38 -42.00  -1.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0097203000
_diffrn_orient_matrix_UB_12      0.0054350000
_diffrn_orient_matrix_UB_13      -0.0344413000
_diffrn_orient_matrix_UB_21      -0.0354611000
_diffrn_orient_matrix_UB_22      0.0594954000
_diffrn_orient_matrix_UB_23      0.0047703000
_diffrn_orient_matrix_UB_31      0.0600820000
_diffrn_orient_matrix_UB_32      0.0359329000
_diffrn_orient_matrix_UB_33      -0.0027704000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.899
_reflns_number_gt                3034
_reflns_number_total             4382
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1003 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(6)
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4382
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0523
_refine_ls_restrained_S_all      1.029
_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)+(0.0812P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1456
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C1'(H1')
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B), C3'(H3'A,H3'B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C4(H4), C7(H7), C1(H1), C6(H6), C3(H3), C2(H2)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C2'(H2'A,H2'B,H2'C), C4'(H4'A,H4'B,H4'C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.06936(19) 0.4474(2) 0.45716(11) 0.0646(6) Uani 1 1 d . . . . .
O2 O 0.3526(2) 0.51094(19) 0.65983(10) 0.0616(6) Uani 1 1 d . . . . .
O1 O 0.3343(2) 0.3071(2) 0.62013(11) 0.0711(7) Uani 1 1 d . . . . .
O3 O 0.1072(2) 0.5058(3) 0.56057(12) 0.0837(8) Uani 1 1 d . . . . .
C14 C 0.1471(3) 0.4656(3) 0.50942(15) 0.0497(7) Uani 1 1 d . . . . .
C8A C 0.5662(2) 0.4651(3) 0.45848(14) 0.0473(7) Uani 1 1 d . . . . .
C11 C 0.3904(2) 0.4768(3) 0.54436(13) 0.0435(6) Uani 1 1 d . . . . .
C16 C 0.3546(3) 0.4225(3) 0.61164(14) 0.0495(7) Uani 1 1 d . . . . .
C5A C 0.5771(3) 0.6013(3) 0.45573(14) 0.0490(7) Uani 1 1 d . . . . .
C13 C 0.2877(3) 0.4249(3) 0.49505(14) 0.0526(8) Uani 1 1 d . . . . .
H13A H 0.311376 0.455790 0.451471 0.063 Uiso 1 1 calc R U . . .
H13B H 0.292090 0.329674 0.494522 0.063 Uiso 1 1 calc R U . . .
C1A C 0.6298(3) 0.4677(3) 0.57330(13) 0.0512(7) Uani 1 1 d . . . . .
C9 C 0.5491(3) 0.6655(3) 0.52081(15) 0.0511(8) Uani 1 1 d . . . . .
H9 H 0.560765 0.761002 0.518534 0.061 Uiso 1 1 calc R U . . .
C4A C 0.6418(3) 0.6041(3) 0.57068(14) 0.0538(8) Uani 1 1 d . . . . .
C8 C 0.6114(3) 0.6622(4) 0.39749(15) 0.0619(9) Uani 1 1 d . . . . .
H8 H 0.618801 0.753246 0.395324 0.074 Uiso 1 1 calc R U . . .
C12 C 0.4057(3) 0.6282(3) 0.54113(15) 0.0502(7) Uani 1 1 d . . . . .
H12A H 0.343262 0.663830 0.509466 0.060 Uiso 1 1 calc R U . . .
H12B H 0.385650 0.665991 0.583790 0.060 Uiso 1 1 calc R U . . .
C5 C 0.5881(3) 0.3887(4) 0.40237(16) 0.0617(9) Uani 1 1 d . . . . .
H5 H 0.578980 0.297802 0.403647 0.074 Uiso 1 1 calc R U . . .
C10 C 0.5290(3) 0.4143(3) 0.52610(14) 0.0464(7) Uani 1 1 d . . . . .
H10 H 0.525899 0.318048 0.527206 0.056 Uiso 1 1 calc R U . . .
C4 C 0.7092(3) 0.3939(4) 0.61579(15) 0.0658(9) Uani 1 1 d . . . . .
H4 H 0.699956 0.303155 0.618562 0.079 Uiso 1 1 calc R U . . .
C7 C 0.6348(4) 0.5856(4) 0.34224(17) 0.0744(10) Uani 1 1 d . . . . .
H7 H 0.658188 0.625845 0.302854 0.089 Uiso 1 1 calc R U . . .
C15 C -0.0716(3) 0.4748(4) 0.4657(2) 0.0740(10) Uani 1 1 d . . . . .
H15A H -0.122263 0.420194 0.436540 0.111 Uiso 1 1 calc R U . . .
H15B H -0.088581 0.565571 0.455890 0.111 Uiso 1 1 calc R U . . .
H15C H -0.096721 0.456806 0.510342 0.111 Uiso 1 1 calc R U . . .
C1 C 0.7340(4) 0.6678(4) 0.61023(16) 0.0736(11) Uani 1 1 d . . . . .
H1 H 0.741160 0.758965 0.609397 0.088 Uiso 1 1 calc R U . . .
C6 C 0.6239(3) 0.4523(4) 0.34485(17) 0.0747(10) Uani 1 1 d . . . . .
H6 H 0.640818 0.403041 0.307261 0.090 Uiso 1 1 calc R U . . .
C3 C 0.8026(4) 0.4603(5) 0.65393(17) 0.0845(12) Uani 1 1 d . . . . .
H3 H 0.857391 0.412635 0.681973 0.101 Uiso 1 1 calc R U . . .
C1' C 0.3151(4) 0.4657(4) 0.72623(16) 0.0757(10) Uani 1 1 d . . . . .
H1' H 0.348591 0.376432 0.733518 0.091 Uiso 1 1 calc R U . . .
C2 C 0.8153(4) 0.5938(5) 0.65099(18) 0.0898(13) Uani 1 1 d . . . . .
H2 H 0.879221 0.635553 0.676580 0.108 Uiso 1 1 calc R U . . .
C3' C 0.3802(7) 0.5583(8) 0.7727(2) 0.148(2) Uani 1 1 d . . . . .
H3'A H 0.348693 0.646270 0.763053 0.178 Uiso 1 1 calc R U . . .
H3'B H 0.351001 0.536663 0.816881 0.178 Uiso 1 1 calc R U . . .
C2' C 0.1662(5) 0.4668(7) 0.7314(3) 0.146(2) Uani 1 1 d . . . . .
H2'A H 0.135007 0.555983 0.731241 0.219 Uiso 1 1 calc R U . . .
H2'B H 0.139704 0.424744 0.771563 0.219 Uiso 1 1 calc R U . . .
H2'C H 0.128791 0.420456 0.694697 0.219 Uiso 1 1 calc R U . . .
C4' C 0.5205(7) 0.5603(9) 0.7723(3) 0.187(3) Uani 1 1 d . . . . .
H4'A H 0.551165 0.599081 0.732031 0.281 Uiso 1 1 calc R U . . .
H4'B H 0.553602 0.472090 0.775670 0.281 Uiso 1 1 calc R U . . .
H4'C H 0.551956 0.611130 0.808880 0.281 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C14 1.333(3) . ?
O4 C15 1.456(4) . ?
O2 C16 1.331(3) . ?
O2 C1' 1.476(4) . ?
O1 C16 1.204(3) . ?
O3 C14 1.188(3) . ?
C14 C13 1.504(4) . ?
C8A C5A 1.391(4) . ?
C8A C5 1.398(4) . ?
C8A C10 1.516(4) . ?
C11 C16 1.519(4) . ?
C11 C13 1.535(4) . ?
C11 C12 1.550(4) . ?
C11 C10 1.577(4) . ?
C5A C9 1.503(4) . ?
C5A C8 1.381(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C1A C4A 1.394(4) . ?
C1A C10 1.499(4) . ?
C1A C4 1.396(4) . ?
C9 H9 0.9800 . ?
C9 C4A 1.513(4) . ?
C9 C12 1.549(4) . ?
C4A C1 1.389(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.388(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C6 1.384(5) . ?
C10 H10 0.9800 . ?
C4 H4 0.9300 . ?
C4 C3 1.393(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.361(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C1 H1 0.9300 . ?
C1 C2 1.387(5) . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.366(6) . ?
C1' H1' 0.9800 . ?
C1' C3' 1.487(7) . ?
C1' C2' 1.503(6) . ?
C2 H2 0.9300 . ?
C3' H3'A 0.9700 . ?
C3' H3'B 0.9700 . ?
C3' C4' 1.413(9) . ?
C2' H2'A 0.9600 . ?
C2' H2'B 0.9600 . ?
C2' H2'C 0.9600 . ?
C4' H4'A 0.9600 . ?
C4' H4'B 0.9600 . ?
C4' H4'C 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
C14 O4 C15 116.8(3) . . ?
C16 O2 C1' 117.8(3) . . ?
O4 C14 C13 111.1(3) . . ?
O3 C14 O4 123.2(3) . . ?
O3 C14 C13 125.7(3) . . ?
C5A C8A C5 120.5(3) . . ?
C5A C8A C10 113.3(2) . . ?
C5 C8A C10 126.2(3) . . ?
C16 C11 C13 107.7(2) . . ?
C16 C11 C12 115.0(2) . . ?
C16 C11 C10 106.0(2) . . ?
C13 C11 C12 112.4(2) . . ?
C13 C11 C10 107.7(2) . . ?
C12 C11 C10 107.7(2) . . ?
O2 C16 C11 114.9(2) . . ?
O1 C16 O2 123.5(3) . . ?
O1 C16 C11 121.6(3) . . ?
C8A C5A C9 112.5(2) . . ?
C8 C5A C8A 120.1(3) . . ?
C8 C5A C9 127.4(3) . . ?
C14 C13 C11 114.4(2) . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C11 C13 H13A 108.7 . . ?
C11 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C4A C1A C10 113.3(3) . . ?
C4A C1A C4 120.6(3) . . ?
C4 C1A C10 126.1(3) . . ?
C5A C9 H9 111.5 . . ?
C5A C9 C4A 107.2(2) . . ?
C5A C9 C12 107.7(2) . . ?
C4A C9 H9 111.5 . . ?
C4A C9 C12 107.2(2) . . ?
C12 C9 H9 111.5 . . ?
C1A C4A C9 112.5(3) . . ?
C1 C4A C1A 120.0(3) . . ?
C1 C4A C9 127.4(3) . . ?
C5A C8 H8 120.5 . . ?
C5A C8 C7 119.0(3) . . ?
C7 C8 H8 120.5 . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C9 C12 C11 110.3(2) . . ?
C9 C12 H12A 109.6 . . ?
C9 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C8A C5 H5 120.9 . . ?
C6 C5 C8A 118.1(3) . . ?
C6 C5 H5 120.9 . . ?
C8A C10 C11 107.1(2) . . ?
C8A C10 H10 111.7 . . ?
C11 C10 H10 111.7 . . ?
C1A C10 C8A 106.9(2) . . ?
C1A C10 C11 107.6(2) . . ?
C1A C10 H10 111.7 . . ?
C1A C4 H4 121.0 . . ?
C3 C4 C1A 118.1(4) . . ?
C3 C4 H4 121.0 . . ?
C8 C7 H7 119.5 . . ?
C6 C7 C8 121.0(3) . . ?
C6 C7 H7 119.5 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4A C1 H1 120.4 . . ?
C2 C1 C4A 119.1(4) . . ?
C2 C1 H1 120.4 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.3(3) . . ?
C7 C6 H6 119.4 . . ?
C4 C3 H3 119.3 . . ?
C2 C3 C4 121.4(4) . . ?
C2 C3 H3 119.3 . . ?
O2 C1' H1' 109.8 . . ?
O2 C1' C3' 105.8(3) . . ?
O2 C1' C2' 108.5(3) . . ?
C3' C1' H1' 109.8 . . ?
C3' C1' C2' 113.0(4) . . ?
C2' C1' H1' 109.8 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.6 . . ?
C1' C3' H3'A 108.2 . . ?
C1' C3' H3'B 108.2 . . ?
H3'A C3' H3'B 107.3 . . ?
C4' C3' C1' 116.5(6) . . ?
C4' C3' H3'A 108.2 . . ?
C4' C3' H3'B 108.2 . . ?
C1' C2' H2'A 109.5 . . ?
C1' C2' H2'B 109.5 . . ?
C1' C2' H2'C 109.5 . . ?
H2'A C2' H2'B 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?
C3' C4' H4'A 109.5 . . ?
C3' C4' H4'B 109.5 . . ?
C3' C4' H4'C 109.5 . . ?
H4'A C4' H4'B 109.5 . . ?
H4'A C4' H4'C 109.5 . . ?
H4'B C4' H4'C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C14 C13 C11 163.9(2) . . . . ?
O2 C1' C3' C4' -63.3(8) . . . . ?
O3 C14 C13 C11 -17.9(5) . . . . ?
C8A C5A C9 C4A 55.3(3) . . . . ?
C8A C5A C9 C12 -59.7(3) . . . . ?
C8A C5A C8 C7 -0.1(5) . . . . ?
C8A C5 C6 C7 -1.4(5) . . . . ?
C16 O2 C1' C3' 153.8(4) . . . . ?
C16 O2 C1' C2' -84.8(5) . . . . ?
C16 C11 C13 C14 60.7(3) . . . . ?
C16 C11 C12 C9 118.4(3) . . . . ?
C16 C11 C10 C8A 179.0(2) . . . . ?
C16 C11 C10 C1A -66.4(3) . . . . ?
C5A C8A C5 C6 1.5(4) . . . . ?
C5A C8A C10 C11 60.0(3) . . . . ?
C5A C8A C10 C1A -55.0(3) . . . . ?
C5A C9 C4A C1A -55.8(3) . . . . ?
C5A C9 C4A C1 122.5(3) . . . . ?
C5A C9 C12 C11 57.4(3) . . . . ?
C5A C8 C7 C6 0.2(5) . . . . ?
C13 C11 C16 O2 -131.8(2) . . . . ?
C13 C11 C16 O1 50.6(4) . . . . ?
C13 C11 C12 C9 -117.9(3) . . . . ?
C13 C11 C10 C8A 64.0(3) . . . . ?
C13 C11 C10 C1A 178.6(3) . . . . ?
C1A C4A C1 C2 1.4(5) . . . . ?
C1A C4 C3 C2 1.1(5) . . . . ?
C9 C5A C8 C7 179.4(3) . . . . ?
C9 C4A C1 C2 -176.9(3) . . . . ?
C4A C1A C10 C8A 54.6(3) . . . . ?
C4A C1A C10 C11 -60.2(3) . . . . ?
C4A C1A C4 C3 -1.7(4) . . . . ?
C4A C9 C12 C11 -57.6(3) . . . . ?
C4A C1 C2 C3 -2.0(6) . . . . ?
C8 C5A C9 C4A -124.2(3) . . . . ?
C8 C5A C9 C12 120.8(3) . . . . ?
C8 C7 C6 C5 0.6(6) . . . . ?
C12 C11 C16 O2 -5.6(3) . . . . ?
C12 C11 C16 O1 176.8(3) . . . . ?
C12 C11 C13 C14 -67.0(3) . . . . ?
C12 C11 C10 C8A -57.4(3) . . . . ?
C12 C11 C10 C1A 57.2(3) . . . . ?
C12 C9 C4A C1A 59.5(3) . . . . ?
C12 C9 C4A C1 -122.1(3) . . . . ?
C5 C8A C5A C9 179.6(2) . . . . ?
C5 C8A C5A C8 -0.8(4) . . . . ?
C5 C8A C10 C11 -119.7(3) . . . . ?
C5 C8A C10 C1A 125.3(3) . . . . ?
C10 C8A C5A C9 -0.1(3) . . . . ?
C10 C8A C5A C8 179.5(2) . . . . ?
C10 C8A C5 C6 -178.8(3) . . . . ?
C10 C11 C16 O2 113.2(3) . . . . ?
C10 C11 C16 O1 -64.4(3) . . . . ?
C10 C11 C13 C14 174.6(3) . . . . ?
C10 C11 C12 C9 0.5(3) . . . . ?
C10 C1A C4A C9 0.3(3) . . . . ?
C10 C1A C4A C1 -178.2(3) . . . . ?
C10 C1A C4 C3 176.8(3) . . . . ?
C4 C1A C4A C9 179.0(2) . . . . ?
C4 C1A C4A C1 0.5(4) . . . . ?
C4 C1A C10 C8A -124.0(3) . . . . ?
C4 C1A C10 C11 121.2(3) . . . . ?
C4 C3 C2 C1 0.8(6) . . . . ?
C15 O4 C14 O3 -2.2(5) . . . . ?
C15 O4 C14 C13 176.1(3) . . . . ?
C1' O2 C16 O1 -4.0(4) . . . . ?
C1' O2 C16 C11 178.5(2) . . . . ?
C2' C1' C3' C4' 178.2(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.688
_oxdiff_exptl_absorpt_empirical_full_min 0.468
####################################################################### 
# 
# 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_pm10as040419
_database_code_depnum_ccdc_archive 'CCDC 1873119'
loop_
_audit_author_name
_audit_author_address
'Saranphong Yimklan'
;Department of Chemistry, Faculty of Science, Chiang Mai University
Thailand
;
_audit_update_record             
;
2021-07-06 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;
_audit_creation_date             2021-07-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H26 O4'
_chemical_formula_sum            'C24 H25 O4'
_chemical_formula_weight         377.44
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.1003(3)
_cell_length_b                   10.1984(3)
_cell_length_c                   20.2551(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2086.42(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13440
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9750
_cell_measurement_theta_min      2.2210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.202
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23892
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.408
_diffrn_reflns_theta_min         2.011
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00  -2.00   0.50   11.70    --   -9.67 -27.00 -24.00  150
  2  ω    -12.00  48.00   0.50   11.70    --   10.38-107.00 140.00  120
  3  ω    -13.00  48.00   0.50   11.70    --   10.38-106.00-126.00  122
  4  ω    -58.00  -3.00   0.50   11.70    --   -9.67 125.00 -30.00  110
  5  ω      3.00  59.00   0.50   11.70    --   10.38-125.00 -60.00  112
  6  ω    -54.00  23.00   0.50   11.70    --   10.38 -37.00 -60.00  154
  7  ω    -54.00  23.00   0.50   11.70    --   10.38 -37.00 -90.00  154
  8  ω      3.00  74.00   0.50   11.70    --   10.38  27.00 138.00  142
  9  ω     -2.00  75.00   0.50   11.70    --   10.38  37.00 -30.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0132594000
_diffrn_orient_matrix_UB_12      0.0665211000
_diffrn_orient_matrix_UB_13      -0.0077934000
_diffrn_orient_matrix_UB_21      -0.0205915000
_diffrn_orient_matrix_UB_22      0.0111916000
_diffrn_orient_matrix_UB_23      0.0330011000
_diffrn_orient_matrix_UB_31      0.0658187000
_diffrn_orient_matrix_UB_32      0.0168939000
_diffrn_orient_matrix_UB_33      0.0087615000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                3251
_reflns_number_total             4502
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 1089 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4502
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0625
_refine_ls_restrained_S_all      1.067
_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)+(0.1234P)²+0.0401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1803
_refine_ls_wR_factor_ref         0.1969
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00P(H00R)
2.b Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B), C00H(H00C,H00H), C00Q(H00S,H00T)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00G(H00G), C00I(H00I), C00K(H00M), C00L(H00N), C00M(H00O),
 C00N(H00P), C00O(H00Q)
2.d Idealised Me refined as rotating group:
 C00J(H00J,H00K,H00L), C00R(H00U,H00V,H00W), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.8915(2) 0.4455(3) 0.53856(12) 0.0655(7) Uani 1 1 d . . . . .
O002 O 0.5969(3) 0.5084(3) 0.33616(13) 0.0725(8) Uani 1 1 d . . . . .
O003 O 0.6208(3) 0.3051(3) 0.37407(14) 0.0822(9) Uani 1 1 d . . . . .
O004 O 0.8523(3) 0.5072(3) 0.43601(15) 0.0890(10) Uani 1 1 d . . . . .
C005 C 0.8137(3) 0.4638(3) 0.48683(17) 0.0553(8) Uani 1 1 d . . . . .
C006 C 0.6011(3) 0.4189(4) 0.38399(17) 0.0575(8) Uani 1 1 d . . . . .
C007 C 0.6753(3) 0.4190(4) 0.50130(17) 0.0576(8) Uani 1 1 d . . . . .
H00A H 0.651924 0.445987 0.545722 0.069 Uiso 1 1 calc R U . . .
H00B H 0.673000 0.323947 0.499992 0.069 Uiso 1 1 calc R U . . .
C008 C 0.5705(3) 0.4728(3) 0.45290(16) 0.0516(8) Uani 1 1 d . . . . .
C009 C 0.3310(3) 0.4652(4) 0.42551(16) 0.0569(8) Uani 1 1 d . . . . .
C00A C 0.3877(3) 0.5972(3) 0.54333(17) 0.0569(8) Uani 1 1 d . . . . .
C00B C 0.3985(3) 0.4599(3) 0.54060(16) 0.0559(8) Uani 1 1 d . . . . .
C00C C 0.3210(3) 0.6015(4) 0.42885(17) 0.0602(9) Uani 1 1 d . . . . .
C00D C 0.3566(4) 0.6568(5) 0.60253(19) 0.0720(10) Uani 1 1 d . . . . .
H00D H 0.351316 0.747714 0.605114 0.086 Uiso 1 1 calc R U . . .
C00E C 0.4323(3) 0.4106(3) 0.47236(16) 0.0521(8) Uani 1 1 d . . . . .
H00E H 0.434919 0.314551 0.470791 0.063 Uiso 1 1 calc R U . . .
C00F C 0.4139(4) 0.6623(4) 0.47803(17) 0.0597(9) Uani 1 1 d . . . . .
H00F H 0.402653 0.757620 0.480545 0.072 Uiso 1 1 calc R U . . .
C00G C 0.3762(4) 0.3844(4) 0.59587(17) 0.0637(9) Uani 1 1 d . . . . .
H00G H 0.384007 0.293603 0.594006 0.076 Uiso 1 1 calc R U . . .
C00H C 0.5572(3) 0.6238(3) 0.4580(2) 0.0601(9) Uani 1 1 d . . . . .
H00C H 0.578724 0.663325 0.415757 0.072 Uiso 1 1 calc R U . . .
H00H H 0.619087 0.656916 0.490569 0.072 Uiso 1 1 calc R U . . .
C00I C 0.2512(4) 0.3940(5) 0.38279(18) 0.0696(11) Uani 1 1 d . . . . .
H00I H 0.259846 0.303475 0.379333 0.084 Uiso 1 1 calc R U . . .
C00J C 1.0309(4) 0.4743(4) 0.5302(2) 0.0768(11) Uani 1 1 d . . . . .
H00J H 1.062131 0.434650 0.490129 0.115 Uiso 1 1 calc R U . . .
H00K H 1.079618 0.439898 0.566987 0.115 Uiso 1 1 calc R U . . .
H00L H 1.043223 0.567543 0.527868 0.115 Uiso 1 1 calc R U . . .
C00K C 0.3415(5) 0.4468(5) 0.65481(19) 0.0804(12) Uani 1 1 d . . . . .
H00M H 0.323847 0.396854 0.692189 0.096 Uiso 1 1 calc R U . . .
C00L C 0.3332(5) 0.5808(5) 0.6582(2) 0.0838(12) Uani 1 1 d . . . . .
H00N H 0.311716 0.621009 0.698031 0.101 Uiso 1 1 calc R U . . .
C00M C 0.2298(5) 0.6663(5) 0.3890(2) 0.0807(12) Uani 1 1 d . . . . .
H00O H 0.223750 0.757248 0.390396 0.097 Uiso 1 1 calc R U . . .
C00N C 0.1577(5) 0.4615(7) 0.3451(2) 0.0968(17) Uani 1 1 d . . . . .
H00P H 0.100312 0.414870 0.317957 0.116 Uiso 1 1 calc R U . . .
C00O C 0.1491(5) 0.5963(6) 0.3476(2) 0.0949(15) Uani 1 1 d . . . . .
H00Q H 0.088146 0.639957 0.321124 0.114 Uiso 1 1 calc R U . . .
C00P C 0.6126(6) 0.4617(6) 0.2676(2) 0.1062(17) Uani 1 1 d . . . . .
H00R H 0.632648 0.367771 0.265112 0.127 Uiso 1 1 calc R U . . .
C00Q C 0.7120(11) 0.5410(16) 0.2368(5) 0.233(6) Uani 1 1 d . . . . .
H00S H 0.717805 0.507763 0.192023 0.280 Uiso 1 1 calc R U . . .
H00T H 0.671866 0.627111 0.233147 0.280 Uiso 1 1 calc R U . . .
C00R C 0.8202(13) 0.5615(16) 0.2518(5) 0.230(6) Uani 1 1 d . . . . .
H00U H 0.875347 0.560767 0.213192 0.346 Uiso 1 1 calc R U . . .
H00V H 0.849702 0.494955 0.281957 0.346 Uiso 1 1 calc R U . . .
H00W H 0.825755 0.645730 0.272762 0.346 Uiso 1 1 calc R U . . .
C1 C 0.4907(11) 0.4956(19) 0.2339(4) 0.339(13) Uani 1 1 d . . . . .
H1A H 0.416644 0.462674 0.258526 0.509 Uiso 1 1 calc R U . . .
H1B H 0.490689 0.457437 0.190556 0.509 Uiso 1 1 calc R U . . .
H1C H 0.484024 0.589244 0.230241 0.509 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C005 1.324(4) . ?
O001 C00J 1.448(4) . ?
O002 C006 1.332(4) . ?
O002 C00P 1.478(6) . ?
O003 C006 1.194(4) . ?
O004 C005 1.186(4) . ?
C005 C007 1.500(5) . ?
C006 C008 1.532(5) . ?
C007 H00A 0.9700 . ?
C007 H00B 0.9700 . ?
C007 C008 1.543(4) . ?
C008 C00E 1.583(4) . ?
C008 C00H 1.550(5) . ?
C009 C00C 1.395(5) . ?
C009 C00E 1.503(5) . ?
C009 C00I 1.388(5) . ?
C00A C00B 1.406(5) . ?
C00A C00D 1.381(5) . ?
C00A C00F 1.503(5) . ?
C00B C00E 1.510(5) . ?
C00B C00G 1.377(5) . ?
C00C C00F 1.502(5) . ?
C00C C00M 1.392(5) . ?
C00D H00D 0.9300 . ?
C00D C00L 1.389(6) . ?
C00E H00E 0.9800 . ?
C00F H00F 0.9800 . ?
C00F C00H 1.554(5) . ?
C00G H00G 0.9300 . ?
C00G C00K 1.398(6) . ?
C00H H00C 0.9700 . ?
C00H H00H 0.9700 . ?
C00I H00I 0.9300 . ?
C00I C00N 1.396(7) . ?
C00J H00J 0.9600 . ?
C00J H00K 0.9600 . ?
C00J H00L 0.9600 . ?
C00K H00M 0.9300 . ?
C00K C00L 1.370(7) . ?
C00L H00N 0.9300 . ?
C00M H00O 0.9300 . ?
C00M C00O 1.370(7) . ?
C00N H00P 0.9300 . ?
C00N C00O 1.378(7) . ?
C00O H00Q 0.9300 . ?
C00P H00R 0.9800 . ?
C00P C00Q 1.432(12) . ?
C00P C1 1.450(11) . ?
C00Q H00S 0.9700 . ?
C00Q H00T 0.9700 . ?
C00Q C00R 1.154(13) . ?
C00R H00U 0.9600 . ?
C00R H00V 0.9600 . ?
C00R H00W 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C005 O001 C00J 117.1(3) . . ?
C006 O002 C00P 117.3(3) . . ?
O001 C005 C007 110.8(3) . . ?
O004 C005 O001 123.0(3) . . ?
O004 C005 C007 126.2(3) . . ?
O002 C006 C008 114.2(3) . . ?
O003 C006 O002 123.3(4) . . ?
O003 C006 C008 122.4(3) . . ?
C005 C007 H00A 108.8 . . ?
C005 C007 H00B 108.8 . . ?
C005 C007 C008 114.0(3) . . ?
H00A C007 H00B 107.7 . . ?
C008 C007 H00A 108.8 . . ?
C008 C007 H00B 108.8 . . ?
C006 C008 C007 108.2(3) . . ?
C006 C008 C00E 105.1(3) . . ?
C006 C008 C00H 115.8(3) . . ?
C007 C008 C00E 107.7(3) . . ?
C007 C008 C00H 111.8(3) . . ?
C00H C008 C00E 107.8(3) . . ?
C00C C009 C00E 112.8(3) . . ?
C00I C009 C00C 120.7(3) . . ?
C00I C009 C00E 126.5(4) . . ?
C00B C00A C00F 113.1(3) . . ?
C00D C00A C00B 119.4(3) . . ?
C00D C00A C00F 127.6(3) . . ?
C00A C00B C00E 112.7(3) . . ?
C00G C00B C00A 120.8(3) . . ?
C00G C00B C00E 126.5(3) . . ?
C009 C00C C00F 113.5(3) . . ?
C00M C00C C009 119.5(4) . . ?
C00M C00C C00F 127.0(4) . . ?
C00A C00D H00D 120.1 . . ?
C00A C00D C00L 119.9(4) . . ?
C00L C00D H00D 120.1 . . ?
C008 C00E H00E 111.6 . . ?
C009 C00E C008 107.1(3) . . ?
C009 C00E C00B 107.5(3) . . ?
C009 C00E H00E 111.6 . . ?
C00B C00E C008 107.1(3) . . ?
C00B C00E H00E 111.6 . . ?
C00A C00F H00F 111.8 . . ?
C00A C00F C00H 106.4(3) . . ?
C00C C00F C00A 106.9(3) . . ?
C00C C00F H00F 111.8 . . ?
C00C C00F C00H 107.7(3) . . ?
C00H C00F H00F 111.8 . . ?
C00B C00G H00G 120.6 . . ?
C00B C00G C00K 118.7(4) . . ?
C00K C00G H00G 120.6 . . ?
C008 C00H C00F 110.4(3) . . ?
C008 C00H H00C 109.6 . . ?
C008 C00H H00H 109.6 . . ?
C00F C00H H00C 109.6 . . ?
C00F C00H H00H 109.6 . . ?
H00C C00H H00H 108.1 . . ?
C009 C00I H00I 120.8 . . ?
C009 C00I C00N 118.4(5) . . ?
C00N C00I H00I 120.8 . . ?
O001 C00J H00J 109.5 . . ?
O001 C00J H00K 109.5 . . ?
O001 C00J H00L 109.5 . . ?
H00J C00J H00K 109.5 . . ?
H00J C00J H00L 109.5 . . ?
H00K C00J H00L 109.5 . . ?
C00G C00K H00M 119.6 . . ?
C00L C00K C00G 120.9(4) . . ?
C00L C00K H00M 119.6 . . ?
C00D C00L H00N 119.8 . . ?
C00K C00L C00D 120.3(4) . . ?
C00K C00L H00N 119.8 . . ?
C00C C00M H00O 120.0 . . ?
C00O C00M C00C 120.1(5) . . ?
C00O C00M H00O 120.0 . . ?
C00I C00N H00P 119.5 . . ?
C00O C00N C00I 121.0(5) . . ?
C00O C00N H00P 119.5 . . ?
C00M C00O C00N 120.3(4) . . ?
C00M C00O H00Q 119.8 . . ?
C00N C00O H00Q 119.8 . . ?
O002 C00P H00R 112.7 . . ?
C00Q C00P O002 107.6(6) . . ?
C00Q C00P H00R 112.7 . . ?
C00Q C00P C1 104.8(8) . . ?
C1 C00P O002 105.9(6) . . ?
C1 C00P H00R 112.7 . . ?
C00P C00Q H00S 104.6 . . ?
C00P C00Q H00T 104.6 . . ?
H00S C00Q H00T 105.7 . . ?
C00R C00Q C00P 130.7(16) . . ?
C00R C00Q H00S 104.6 . . ?
C00R C00Q H00T 104.6 . . ?
C00Q C00R H00U 109.5 . . ?
C00Q C00R H00V 109.5 . . ?
C00Q C00R H00W 109.5 . . ?
H00U C00R H00V 109.5 . . ?
H00U C00R H00W 109.5 . . ?
H00V C00R H00W 109.5 . . ?
C00P C1 H1A 109.5 . . ?
C00P C1 H1B 109.5 . . ?
C00P C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C005 C007 C008 162.9(3) . . . . ?
O002 C006 C008 C007 -133.8(3) . . . . ?
O002 C006 C008 C00E 111.3(3) . . . . ?
O002 C006 C008 C00H -7.5(4) . . . . ?
O002 C00P C00Q C00R 56.3(19) . . . . ?
O003 C006 C008 C007 49.6(4) . . . . ?
O003 C006 C008 C00E -65.3(4) . . . . ?
O003 C006 C008 C00H 175.9(3) . . . . ?
O004 C005 C007 C008 -18.9(6) . . . . ?
C005 C007 C008 C006 63.7(4) . . . . ?
C005 C007 C008 C00E 176.9(3) . . . . ?
C005 C007 C008 C00H -64.9(4) . . . . ?
C006 O002 C00P C00Q -129.8(8) . . . . ?
C006 O002 C00P C1 118.5(9) . . . . ?
C006 C008 C00E C009 -65.6(3) . . . . ?
C006 C008 C00E C00B 179.4(3) . . . . ?
C006 C008 C00H C00F 115.7(3) . . . . ?
C007 C008 C00E C009 179.2(3) . . . . ?
C007 C008 C00E C00B 64.1(3) . . . . ?
C007 C008 C00H C00F -119.8(3) . . . . ?
C009 C00C C00F C00A -55.2(4) . . . . ?
C009 C00C C00F C00H 58.8(4) . . . . ?
C009 C00C C00M C00O 1.1(6) . . . . ?
C009 C00I C00N C00O 3.3(6) . . . . ?
C00A C00B C00E C008 60.5(3) . . . . ?
C00A C00B C00E C009 -54.3(4) . . . . ?
C00A C00B C00G C00K 0.5(6) . . . . ?
C00A C00D C00L C00K 0.4(7) . . . . ?
C00A C00F C00H C008 58.9(4) . . . . ?
C00B C00A C00D C00L -1.6(6) . . . . ?
C00B C00A C00F C00C 55.1(4) . . . . ?
C00B C00A C00F C00H -59.7(4) . . . . ?
C00B C00G C00K C00L -1.7(7) . . . . ?
C00C C009 C00E C008 -60.2(3) . . . . ?
C00C C009 C00E C00B 54.6(4) . . . . ?
C00C C009 C00I C00N -2.3(5) . . . . ?
C00C C00F C00H C008 -55.4(4) . . . . ?
C00C C00M C00O C00N -0.1(7) . . . . ?
C00D C00A C00B C00E 179.7(3) . . . . ?
C00D C00A C00B C00G 1.1(5) . . . . ?
C00D C00A C00F C00C -125.3(4) . . . . ?
C00D C00A C00F C00H 119.8(4) . . . . ?
C00E C008 C00H C00F -1.7(4) . . . . ?
C00E C009 C00C C00F 0.3(4) . . . . ?
C00E C009 C00C C00M -179.1(3) . . . . ?
C00E C009 C00I C00N 176.8(3) . . . . ?
C00E C00B C00G C00K -177.9(3) . . . . ?
C00F C00A C00B C00E -0.7(4) . . . . ?
C00F C00A C00B C00G -179.3(3) . . . . ?
C00F C00A C00D C00L 178.9(4) . . . . ?
C00F C00C C00M C00O -178.2(4) . . . . ?
C00G C00B C00E C008 -121.0(4) . . . . ?
C00G C00B C00E C009 124.2(4) . . . . ?
C00G C00K C00L C00D 1.3(7) . . . . ?
C00H C008 C00E C009 58.5(4) . . . . ?
C00H C008 C00E C00B -56.6(3) . . . . ?
C00I C009 C00C C00F 179.5(3) . . . . ?
C00I C009 C00C C00M 0.1(5) . . . . ?
C00I C009 C00E C008 120.6(4) . . . . ?
C00I C009 C00E C00B -124.6(3) . . . . ?
C00I C00N C00O C00M -2.1(7) . . . . ?
C00J O001 C005 O004 -3.2(5) . . . . ?
C00J O001 C005 C007 175.1(3) . . . . ?
C00M C00C C00F C00A 124.1(4) . . . . ?
C00M C00C C00F C00H -121.9(4) . . . . ?
C00P O002 C006 O003 2.3(6) . . . . ?
C00P O002 C006 C008 -174.3(4) . . . . ?
C1 C00P C00Q C00R 168.7(18) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.056 0.278 0.269 7.1 0.6 ?
2 0.056 0.778 0.231 7.1 0.6 ?
3 0.444 0.222 0.731 7.1 0.6 ?
4 0.556 0.722 0.769 7.1 0.6 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.719
_oxdiff_exptl_absorpt_empirical_full_min 0.730
####################################################################### 
# 
# 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_pm04as290519
_database_code_depnum_ccdc_archive 'CCDC 2094086'
loop_
_audit_author_name
_audit_author_address
'Saranphong Yimklan'
;Department of Chemistry, Faculty of Science, Chiang Mai University
Thailand
;
_audit_update_record             
;
2021-07-05 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;
_audit_creation_date             2021-07-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H26 O4'
_chemical_formula_sum            'C24 H26 O4'
_chemical_formula_weight         378.45
_chemical_absolute_configuration rm
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.1047(2)
_cell_length_b                   10.1997(3)
_cell_length_c                   20.2588(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2087.97(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14098
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9470
_cell_measurement_theta_min      2.0000
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26461
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.457
_diffrn_reflns_theta_min         2.010
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  74.00   0.50    8.00    --   10.38  64.00-102.00  168
  2  ω    -53.00  28.00   0.50    8.00    --   10.38 -57.00 -76.00  162
  3  ω     -3.00  54.00   0.50    8.00    --   10.38-118.00  49.00  114
  4  ω    -58.00  -3.00   0.50    8.00    --   -9.67 125.00  90.00  110
  5  ω    -19.00  44.00   0.50    8.00    --   10.38 -99.00  30.00  126
  6  ω     -7.00  74.00   0.50    8.00    --   10.38  57.00-120.00  162
  7  ω    -53.00  28.00   0.50    8.00    --   10.38 -57.00  60.00  162
  8  ω    -60.00  23.00   0.50    8.00    --   10.38 -19.00 150.00  166
  9  ω    -15.00  69.00   0.50    8.00    --   10.38  77.00  60.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0475936000
_diffrn_orient_matrix_UB_12      0.0509933000
_diffrn_orient_matrix_UB_13      0.0015619000
_diffrn_orient_matrix_UB_21      -0.0047917000
_diffrn_orient_matrix_UB_22      0.0086176000
_diffrn_orient_matrix_UB_23      -0.0346662000
_diffrn_orient_matrix_UB_31      -0.0513786000
_diffrn_orient_matrix_UB_32      0.0464695000
_diffrn_orient_matrix_UB_33      0.0046937000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                3170
_reflns_number_total             4494
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1072 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_coef       0.012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0604
_refine_ls_restrained_S_all      1.079
_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)+(0.1198P)²+0.0195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1758
_refine_ls_wR_factor_ref         0.1937
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C9(H9), C1'(H1')
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C10(H10A,H10B), C3'(H3'A,H3'B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1), C5(H5), C8(H8), C6(H6), C3(H3), C2(H2), C7(H7)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C2'(H2'A,H2'B,H2'C), C4'(H4'A,H4'B,H4'C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.1084(2) 0.5543(3) 0.53846(12) 0.0683(7) Uani 1 1 d . . . . .
O4 O 0.4033(3) 0.4913(3) 0.33628(14) 0.0749(8) Uani 1 1 d . . . . .
O3 O 0.3791(3) 0.6947(3) 0.37441(14) 0.0835(9) Uani 1 1 d . . . . .
O1 O 0.1481(3) 0.4924(3) 0.43590(15) 0.0912(10) Uani 1 1 d . . . . .
C14 C 0.1862(3) 0.5362(3) 0.48627(18) 0.0571(8) Uani 1 1 d . . . . .
C16 C 0.3984(3) 0.5811(3) 0.38443(17) 0.0579(8) Uani 1 1 d . . . . .
C5A C 0.6687(3) 0.5350(4) 0.42522(16) 0.0586(8) Uani 1 1 d . . . . .
C11 C 0.4292(3) 0.5277(3) 0.45240(16) 0.0523(8) Uani 1 1 d . . . . .
C13 C 0.3248(3) 0.5810(4) 0.50105(17) 0.0596(9) Uani 1 1 d . . . . .
H13A H 0.348107 0.553279 0.545353 0.072 Uiso 1 1 calc R U . . .
H13B H 0.327125 0.676006 0.500075 0.072 Uiso 1 1 calc R U . . .
C4A C 0.6120(3) 0.4027(3) 0.54305(16) 0.0580(8) Uani 1 1 d . . . . .
C8A C 0.6786(3) 0.3982(4) 0.42880(17) 0.0629(9) Uani 1 1 d . . . . .
C4 C 0.6434(4) 0.3431(4) 0.60227(19) 0.0741(10) Uani 1 1 d . . . . .
H4 H 0.649385 0.252221 0.604893 0.089 Uiso 1 1 calc R U . . .
C12 C 0.5672(3) 0.5894(3) 0.47240(16) 0.0534(8) Uani 1 1 d . . . . .
H12 H 0.564578 0.685403 0.470920 0.064 Uiso 1 1 calc R U . . .
C1A C 0.6015(3) 0.5401(3) 0.54067(16) 0.0577(8) Uani 1 1 d . . . . .
C9 C 0.5861(4) 0.3379(3) 0.47829(17) 0.0623(9) Uani 1 1 d . . . . .
H9 H 0.597297 0.242656 0.480950 0.075 Uiso 1 1 calc R U . . .
C10 C 0.4424(3) 0.3762(3) 0.4577(2) 0.0618(9) Uani 1 1 d . . . . .
H10A H 0.421327 0.336416 0.415542 0.074 Uiso 1 1 calc R U . . .
H10B H 0.380239 0.343283 0.490237 0.074 Uiso 1 1 calc R U . . .
C15 C -0.0312(3) 0.5259(4) 0.5302(2) 0.0773(11) Uani 1 1 d . . . . .
H15A H -0.064111 0.571415 0.492116 0.116 Uiso 1 1 calc R U . . .
H15B H -0.078736 0.554346 0.568673 0.116 Uiso 1 1 calc R U . . .
H15C H -0.043168 0.433294 0.524414 0.116 Uiso 1 1 calc R U . . .
C1 C 0.6240(4) 0.6153(4) 0.59575(17) 0.0667(10) Uani 1 1 d . . . . .
H1 H 0.616685 0.706063 0.593780 0.080 Uiso 1 1 calc R U . . .
C5 C 0.7487(4) 0.6056(5) 0.38262(18) 0.0723(11) Uani 1 1 d . . . . .
H5 H 0.740161 0.696236 0.379554 0.087 Uiso 1 1 calc R U . . .
C8 C 0.7698(5) 0.3333(5) 0.3886(2) 0.0818(12) Uani 1 1 d . . . . .
H8 H 0.776040 0.242319 0.389638 0.098 Uiso 1 1 calc R U . . .
C6 C 0.8413(5) 0.5402(7) 0.3446(2) 0.0968(15) Uani 1 1 d . . . . .
H6 H 0.897735 0.587268 0.317196 0.116 Uiso 1 1 calc R U . . .
C3 C 0.6660(5) 0.4193(5) 0.6577(2) 0.0854(12) Uani 1 1 d . . . . .
H3 H 0.686979 0.379288 0.697562 0.103 Uiso 1 1 calc R U . . .
C2 C 0.6578(5) 0.5537(5) 0.65429(19) 0.0794(11) Uani 1 1 d . . . . .
H2 H 0.675094 0.603720 0.691691 0.095 Uiso 1 1 calc R U . . .
C7 C 0.8504(5) 0.4050(6) 0.3473(2) 0.0970(15) Uani 1 1 d . . . . .
H7 H 0.911890 0.361958 0.320929 0.116 Uiso 1 1 calc R U . . .
C1' C 0.3869(6) 0.5389(6) 0.2676(2) 0.1096(17) Uani 1 1 d . . . . .
H1' H 0.367375 0.632857 0.265124 0.132 Uiso 1 1 calc R U . . .
C3' C 0.2905(11) 0.4603(16) 0.2354(5) 0.236(6) Uani 1 1 d . . . . .
H3'A H 0.286518 0.494262 0.190700 0.283 Uiso 1 1 calc R U . . .
H3'B H 0.330803 0.374287 0.231885 0.283 Uiso 1 1 calc R U . . .
C2' C 0.5074(12) 0.5037(19) 0.2343(4) 0.362(14) Uani 1 1 d . . . . .
H2'A H 0.510494 0.410408 0.228422 0.543 Uiso 1 1 calc R U . . .
H2'B H 0.581801 0.531315 0.260321 0.543 Uiso 1 1 calc R U . . .
H2'C H 0.510388 0.546043 0.192026 0.543 Uiso 1 1 calc R U . . .
C4' C 0.1803(13) 0.4399(15) 0.2498(5) 0.232(5) Uani 1 1 d . . . . .
H4'A H 0.149170 0.508207 0.278414 0.347 Uiso 1 1 calc R U . . .
H4'B H 0.174429 0.357079 0.272099 0.347 Uiso 1 1 calc R U . . .
H4'C H 0.126942 0.437585 0.210584 0.347 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C14 1.330(4) . ?
O2 C15 1.450(4) . ?
O4 C16 1.339(4) . ?
O4 C1' 1.483(6) . ?
O3 C16 1.193(4) . ?
O1 C14 1.178(4) . ?
C14 C13 1.503(5) . ?
C16 C11 1.513(5) . ?
C5A C8A 1.401(5) . ?
C5A C12 1.508(4) . ?
C5A C5 1.385(5) . ?
C11 C13 1.543(4) . ?
C11 C12 1.583(4) . ?
C11 C10 1.555(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C4A C4 1.382(5) . ?
C4A C1A 1.406(5) . ?
C4A C9 1.492(5) . ?
C8A C9 1.502(5) . ?
C8A C8 1.398(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.385(6) . ?
C12 H12 0.9800 . ?
C12 C1A 1.512(5) . ?
C1A C1 1.373(5) . ?
C9 H9 0.9800 . ?
C9 C10 1.559(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C1 H1 0.9300 . ?
C1 C2 1.385(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(7) . ?
C8 H8 0.9300 . ?
C8 C7 1.378(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.382(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.374(6) . ?
C2 H2 0.9300 . ?
C7 H7 0.9300 . ?
C1' H1' 0.9800 . ?
C1' C3' 1.420(11) . ?
C1' C2' 1.437(11) . ?
C3' H3'A 0.9700 . ?
C3' H3'B 0.9700 . ?
C3' C4' 1.170(13) . ?
C2' H2'A 0.9600 . ?
C2' H2'B 0.9600 . ?
C2' H2'C 0.9600 . ?
C4' H4'A 0.9600 . ?
C4' H4'B 0.9600 . ?
C4' H4'C 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
C14 O2 C15 117.1(3) . . ?
C16 O4 C1' 117.1(3) . . ?
O2 C14 C13 110.5(3) . . ?
O1 C14 O2 123.3(3) . . ?
O1 C14 C13 126.3(3) . . ?
O4 C16 C11 114.2(3) . . ?
O3 C16 O4 123.1(4) . . ?
O3 C16 C11 122.6(3) . . ?
C8A C5A C12 112.5(3) . . ?
C5 C5A C8A 120.6(3) . . ?
C5 C5A C12 126.9(3) . . ?
C16 C11 C13 108.3(3) . . ?
C16 C11 C12 105.7(3) . . ?
C16 C11 C10 116.0(3) . . ?
C13 C11 C12 107.4(2) . . ?
C13 C11 C10 111.4(3) . . ?
C10 C11 C12 107.6(2) . . ?
C14 C13 C11 113.8(3) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C11 C13 H13A 108.8 . . ?
C11 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C4 C4A C1A 119.1(3) . . ?
C4 C4A C9 127.5(3) . . ?
C1A C4A C9 113.4(3) . . ?
C5A C8A C9 113.4(3) . . ?
C8 C8A C5A 119.3(4) . . ?
C8 C8A C9 127.3(4) . . ?
C4A C4 H4 120.2 . . ?
C4A C4 C3 119.6(4) . . ?
C3 C4 H4 120.2 . . ?
C5A C12 C11 106.9(2) . . ?
C5A C12 H12 111.5 . . ?
C5A C12 C1A 107.5(3) . . ?
C11 C12 H12 111.5 . . ?
C1A C12 C11 107.7(3) . . ?
C1A C12 H12 111.5 . . ?
C4A C1A C12 112.3(3) . . ?
C1 C1A C4A 121.1(3) . . ?
C1 C1A C12 126.6(3) . . ?
C4A C9 C8A 107.2(3) . . ?
C4A C9 H9 111.7 . . ?
C4A C9 C10 106.7(3) . . ?
C8A C9 H9 111.7 . . ?
C8A C9 C10 107.4(3) . . ?
C10 C9 H9 111.7 . . ?
C11 C10 C9 110.3(3) . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1A C1 H1 120.5 . . ?
C1A C1 C2 118.9(4) . . ?
C2 C1 H1 120.5 . . ?
C5A C5 H5 120.3 . . ?
C6 C5 C5A 119.4(4) . . ?
C6 C5 H5 120.3 . . ?
C8A C8 H8 120.3 . . ?
C7 C8 C8A 119.5(4) . . ?
C7 C8 H8 120.3 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.3(5) . . ?
C7 C6 H6 119.9 . . ?
C4 C3 H3 119.7 . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 H3 119.7 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 H2 119.7 . . ?
C8 C7 C6 121.0(4) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
O4 C1' H1' 113.0 . . ?
C3' C1' O4 108.9(6) . . ?
C3' C1' H1' 113.0 . . ?
C3' C1' C2' 103.0(8) . . ?
C2' C1' O4 105.3(6) . . ?
C2' C1' H1' 113.0 . . ?
C1' C3' H3'A 104.9 . . ?
C1' C3' H3'B 104.9 . . ?
H3'A C3' H3'B 105.8 . . ?
C4' C3' C1' 129.7(15) . . ?
C4' C3' H3'A 104.9 . . ?
C4' C3' H3'B 104.9 . . ?
C1' C2' H2'A 109.5 . . ?
C1' C2' H2'B 109.5 . . ?
C1' C2' H2'C 109.5 . . ?
H2'A C2' H2'B 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?
C3' C4' H4'A 109.5 . . ?
C3' C4' H4'B 109.5 . . ?
C3' C4' H4'C 109.5 . . ?
H4'A C4' H4'B 109.5 . . ?
H4'A C4' H4'C 109.5 . . ?
H4'B C4' H4'C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C14 C13 C11 163.0(3) . . . . ?
O4 C16 C11 C13 -134.1(3) . . . . ?
O4 C16 C11 C12 111.0(3) . . . . ?
O4 C16 C11 C10 -8.1(4) . . . . ?
O4 C1' C3' C4' 57.4(19) . . . . ?
O3 C16 C11 C13 50.0(4) . . . . ?
O3 C16 C11 C12 -64.8(4) . . . . ?
O3 C16 C11 C10 176.1(3) . . . . ?
O1 C14 C13 C11 -18.0(5) . . . . ?
C16 O4 C1' C3' -130.6(8) . . . . ?
C16 O4 C1' C2' 119.5(9) . . . . ?
C16 C11 C13 C14 63.3(4) . . . . ?
C16 C11 C12 C5A -65.4(3) . . . . ?
C16 C11 C12 C1A 179.3(2) . . . . ?
C16 C11 C10 C9 116.2(3) . . . . ?
C5A C8A C9 C4A -55.1(4) . . . . ?
C5A C8A C9 C10 59.2(4) . . . . ?
C5A C8A C8 C7 1.5(6) . . . . ?
C5A C12 C1A C4A -54.6(3) . . . . ?
C5A C12 C1A C1 124.0(3) . . . . ?
C5A C5 C6 C7 2.5(6) . . . . ?
C11 C12 C1A C4A 60.3(3) . . . . ?
C11 C12 C1A C1 -121.1(4) . . . . ?
C13 C11 C12 C5A 179.1(3) . . . . ?
C13 C11 C12 C1A 63.8(3) . . . . ?
C13 C11 C10 C9 -119.3(3) . . . . ?
C4A C4 C3 C2 -0.2(7) . . . . ?
C4A C1A C1 C2 0.2(6) . . . . ?
C4A C9 C10 C11 58.9(4) . . . . ?
C8A C5A C12 C11 -60.8(3) . . . . ?
C8A C5A C12 C1A 54.6(3) . . . . ?
C8A C5A C5 C6 -1.7(5) . . . . ?
C8A C9 C10 C11 -55.8(4) . . . . ?
C8A C8 C7 C6 -0.7(7) . . . . ?
C4 C4A C1A C12 179.8(3) . . . . ?
C4 C4A C1A C1 1.0(5) . . . . ?
C4 C4A C9 C8A -125.1(4) . . . . ?
C4 C4A C9 C10 120.1(4) . . . . ?
C4 C3 C2 C1 1.4(7) . . . . ?
C12 C5A C8A C9 0.2(4) . . . . ?
C12 C5A C8A C8 -179.2(3) . . . . ?
C12 C5A C5 C6 177.0(3) . . . . ?
C12 C11 C13 C14 177.1(3) . . . . ?
C12 C11 C10 C9 -1.9(4) . . . . ?
C12 C1A C1 C2 -178.4(3) . . . . ?
C1A C4A C4 C3 -1.0(6) . . . . ?
C1A C4A C9 C8A 55.1(4) . . . . ?
C1A C4A C9 C10 -59.7(4) . . . . ?
C1A C1 C2 C3 -1.4(6) . . . . ?
C9 C4A C4 C3 179.2(4) . . . . ?
C9 C4A C1A C12 -0.4(4) . . . . ?
C9 C4A C1A C1 -179.2(3) . . . . ?
C9 C8A C8 C7 -177.8(4) . . . . ?
C10 C11 C13 C14 -65.4(4) . . . . ?
C10 C11 C12 C5A 59.1(3) . . . . ?
C10 C11 C12 C1A -56.2(3) . . . . ?
C15 O2 C14 O1 -4.1(5) . . . . ?
C15 O2 C14 C13 175.0(3) . . . . ?
C5 C5A C8A C9 179.1(3) . . . . ?
C5 C5A C8A C8 -0.3(5) . . . . ?
C5 C5A C12 C11 120.4(4) . . . . ?
C5 C5A C12 C1A -124.2(3) . . . . ?
C5 C6 C7 C8 -1.3(7) . . . . ?
C8 C8A C9 C4A 124.2(4) . . . . ?
C8 C8A C9 C10 -121.4(4) . . . . ?
C1' O4 C16 O3 1.6(5) . . . . ?
C1' O4 C16 C11 -174.3(4) . . . . ?
C2' C1' C3' C4' 168.8(18) . . . . ?

_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 1.690
_oxdiff_exptl_absorpt_empirical_full_min 0.453


# start Validation Reply Form

_vrf_PLAT360_pm04as290519        
;
PROBLEM: Short  C(sp3)-C(sp3) Bond  C3'      - C4'      .       1.17 Ang.  
RESPONSE: This alert is genertated due to the severe disorder 
in the particular alkyl group.
;
_vrf_PLAT220_pm04as290519        
;
PROBLEM: NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        7.0 Ratio 
RESPONSE: This alert is genertated due to the severe disorder 
in the particular alkyl group.
;
_vrf_PLAT241_pm04as290519        
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of        C3' Check 
RESPONSE: This alert is genertated due to the severe disorder 
in the particular alkyl group.
;
_vrf_PLAT242_pm04as290519        
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        C1' Check 
RESPONSE: This alert is genertated due to the severe disorder 
in the particular alkyl group.
;
_vrf_PLAT412_pm04as290519        
;
PROBLEM: Short Intra XH3 .. XHn     H3'A     ..H4'C     .       1.76 Ang.  
RESPONSE: This alert is genertated due to the severe disorder 
in the particular alkyl group.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_pm01as210619r1
_database_code_depnum_ccdc_archive 'CCDC 2094178'
loop_
_audit_author_name
_audit_author_address
'Saranphong Yimklan'
;Department of Chemistry, Faculty of Science, Chiang Mai University
Thailand
;
_audit_update_record             
;
2021-07-03 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;
_audit_creation_date             2019-07-01
_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         'C24 H26 O4'
_chemical_formula_sum            'C24 H26 O4'
_chemical_formula_weight         378.45
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.0659(2)
_cell_length_b                   10.1740(3)
_cell_length_c                   20.3251(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2081.50(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12369
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4620
_cell_measurement_theta_min      2.2210
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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             808
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23193
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.443
_diffrn_reflns_theta_min         2.239
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00  10.00   0.50    6.10    --   -9.67 110.00 -41.00  118
  2  ω    -50.00   8.00   0.50    6.10    --   -9.67 112.00-134.00  116
  3  ω      0.00  80.00   0.50    6.10    --   10.38  21.00 131.00  160
  4  ω      3.00  59.00   0.50    6.10    --   10.38-125.00  90.00  112
  5  ω      3.00  59.00   0.50    6.10    --   10.38-125.00 -60.00  112
  6  ω    -15.00  75.00   0.50    6.10    --   10.38  77.00-120.00  180
  7  ω    -54.00  23.00   0.50    6.10    --   10.38 -37.00 -60.00  154
  8  ω    -15.00  37.00   0.50    6.10    --   10.38  77.00   0.00  104
  9  ω    -60.00  23.00   0.50    6.10    --   10.38 -19.00 120.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0131667000
_diffrn_orient_matrix_UB_12      0.0017875000
_diffrn_orient_matrix_UB_13      -0.0342644000
_diffrn_orient_matrix_UB_21      0.0147782000
_diffrn_orient_matrix_UB_22      -0.0681661000
_diffrn_orient_matrix_UB_23      0.0005041000
_diffrn_orient_matrix_UB_31      -0.0676371000
_diffrn_orient_matrix_UB_32      -0.0145566000
_diffrn_orient_matrix_UB_33      -0.0065533000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                3228
_reflns_number_total             4427
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1087 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.059
_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)+(0.0722P)²+0.1176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1412
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C1'(H1')
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B), C3'(H3'A,H3'B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1), C8(H8), C5(H5), C3(H3), C2(H2), C7(H7), C6(H6)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C2'(H2'A,H2'B,H2'C), C4'(H4'A,H4'B,H4'C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.93078(19) 0.4478(2) 0.45716(11) 0.0640(6) Uani 1 1 d . . . . .
O4 O 0.6478(2) 0.5110(2) 0.65960(10) 0.0600(6) Uani 1 1 d . . . . .
O3 O 0.6662(2) 0.3070(3) 0.62005(11) 0.0701(7) Uani 1 1 d . . . . .
O1 O 0.8929(2) 0.5062(3) 0.56043(12) 0.0821(8) Uani 1 1 d . . . . .
C14 C 0.8533(3) 0.4656(3) 0.50935(14) 0.0480(7) Uani 1 1 d . . . . .
C16 C 0.6463(3) 0.4230(3) 0.61169(14) 0.0478(7) Uani 1 1 d . . . . .
C11 C 0.6100(2) 0.4769(3) 0.54421(13) 0.0429(6) Uani 1 1 d . . . . .
C1A C 0.4343(2) 0.4642(3) 0.45833(14) 0.0462(7) Uani 1 1 d . . . . .
C4A C 0.4230(3) 0.6013(3) 0.45564(14) 0.0487(7) Uani 1 1 d . . . . .
C8A C 0.3705(3) 0.4678(4) 0.57327(13) 0.0503(7) Uani 1 1 d . . . . .
C9 C 0.4511(3) 0.6662(3) 0.52086(14) 0.0509(7) Uani 1 1 d . . . . .
H9 H 0.439274 0.761673 0.518564 0.061 Uiso 1 1 calc R . . . .
C13 C 0.7126(3) 0.4243(3) 0.49509(15) 0.0516(7) Uani 1 1 d . . . . .
H13A H 0.708351 0.329082 0.494977 0.062 Uiso 1 1 calc R . . . .
H13B H 0.688794 0.454453 0.451370 0.062 Uiso 1 1 calc R . . . .
C5A C 0.3580(3) 0.6042(3) 0.57062(14) 0.0530(8) Uani 1 1 d . . . . .
C12 C 0.5946(3) 0.6287(3) 0.54085(16) 0.0494(7) Uani 1 1 d . . . . .
H12A H 0.615134 0.666643 0.583445 0.059 Uiso 1 1 calc R . . . .
H12B H 0.656763 0.664210 0.508983 0.059 Uiso 1 1 calc R . . . .
C4 C 0.3890(3) 0.6624(4) 0.39751(15) 0.0611(9) Uani 1 1 d . . . . .
H4 H 0.382366 0.753426 0.395327 0.073 Uiso 1 1 calc R . . . .
C10 C 0.4713(3) 0.4138(3) 0.52598(14) 0.0454(7) Uani 1 1 d . . . . .
H10 H 0.474430 0.317541 0.527263 0.054 Uiso 1 1 calc R . . . .
C1 C 0.4125(3) 0.3893(4) 0.40258(15) 0.0601(9) Uani 1 1 d . . . . .
H1 H 0.422270 0.298387 0.403808 0.072 Uiso 1 1 calc R . . . .
C8 C 0.2910(3) 0.3944(4) 0.61578(15) 0.0649(9) Uani 1 1 d . . . . .
H8 H 0.300455 0.303680 0.618612 0.078 Uiso 1 1 calc R . . . .
C5 C 0.2660(4) 0.6677(5) 0.61007(16) 0.0725(11) Uani 1 1 d . . . . .
H5 H 0.258565 0.758763 0.609157 0.087 Uiso 1 1 calc R . . . .
C3 C 0.3647(4) 0.5859(5) 0.34230(17) 0.0742(10) Uani 1 1 d . . . . .
H3 H 0.340425 0.626376 0.303066 0.089 Uiso 1 1 calc R . . . .
C2 C 0.3758(3) 0.4524(5) 0.34460(17) 0.0727(10) Uani 1 1 d . . . . .
H2 H 0.358590 0.403028 0.307042 0.087 Uiso 1 1 calc R . . . .
C15 C 1.0717(3) 0.4744(4) 0.4661(2) 0.0735(10) Uani 1 1 d . . . . .
H15A H 1.122576 0.417101 0.438339 0.110 Uiso 1 1 calc GR . . . .
H15B H 1.095442 0.459463 0.511269 0.110 Uiso 1 1 calc GR . . . .
H15C H 1.089929 0.564156 0.454743 0.110 Uiso 1 1 calc GR . . . .
C7 C 0.1974(4) 0.4599(6) 0.65380(17) 0.0834(12) Uani 1 1 d . . . . .
H7 H 0.142100 0.412154 0.681607 0.100 Uiso 1 1 calc R . . . .
C6 C 0.1853(4) 0.5936(6) 0.65089(18) 0.0867(13) Uani 1 1 d . . . . .
H6 H 0.121945 0.635413 0.676757 0.104 Uiso 1 1 calc R . . . .
C1' C 0.6848(4) 0.4651(4) 0.72605(16) 0.0734(10) Uani 1 1 d . . . . .
H1' H 0.651617 0.375696 0.733219 0.088 Uiso 1 1 calc R . . . .
C3' C 0.6198(7) 0.5583(8) 0.7731(2) 0.145(2) Uani 1 1 d . . . . .
H3'A H 0.648126 0.535676 0.817281 0.174 Uiso 1 1 calc R . . . .
H3'B H 0.652292 0.646130 0.763871 0.174 Uiso 1 1 calc R . . . .
C2' C 0.8343(5) 0.4672(8) 0.7311(3) 0.147(2) Uani 1 1 d . . . . .
H2'A H 0.871898 0.422441 0.693913 0.221 Uiso 1 1 calc GR . . . .
H2'B H 0.861336 0.424013 0.770861 0.221 Uiso 1 1 calc GR . . . .
H2'C H 0.864765 0.556649 0.731642 0.221 Uiso 1 1 calc GR . . . .
C4' C 0.4807(7) 0.5616(11) 0.7722(3) 0.196(4) Uani 1 1 d . . . . .
H4'A H 0.450906 0.598993 0.731372 0.294 Uiso 1 1 calc GR . . . .
H4'B H 0.449169 0.614259 0.808117 0.294 Uiso 1 1 calc GR . . . .
H4'C H 0.446614 0.473879 0.776341 0.294 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
O2 C14 1.329(3) . ?
O2 C15 1.455(4) . ?
O4 C16 1.323(3) . ?
O4 C1' 1.477(4) . ?
O3 C16 1.209(4) . ?
O1 C14 1.186(3) . ?
C14 C13 1.505(4) . ?
C16 C11 1.521(4) . ?
C11 C13 1.532(4) . ?
C11 C12 1.554(4) . ?
C11 C10 1.581(4) . ?
C1A C4A 1.401(4) . ?
C1A C10 1.514(4) . ?
C1A C1 1.383(4) . ?
C4A C9 1.507(4) . ?
C4A C4 1.378(4) . ?
C8A C5A 1.394(5) . ?
C8A C10 1.502(4) . ?
C8A C8 1.394(4) . ?
C9 C5A 1.516(4) . ?
C9 C12 1.549(4) . ?
C5A C5 1.385(5) . ?
C4 C3 1.387(5) . ?
C1 C2 1.392(5) . ?
C8 C7 1.389(5) . ?
C5 C6 1.384(6) . ?
C3 C2 1.364(6) . ?
C7 C6 1.366(6) . ?
C1' C3' 1.497(7) . ?
C1' C2' 1.508(7) . ?
C3' C4' 1.401(9) . ?

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
C14 O2 C15 116.5(3) . . ?
C16 O4 C1' 117.5(3) . . ?
O2 C14 C13 111.1(3) . . ?
O1 C14 O2 123.3(3) . . ?
O1 C14 C13 125.6(3) . . ?
O4 C16 C11 115.0(3) . . ?
O3 C16 O4 123.7(3) . . ?
O3 C16 C11 121.2(3) . . ?
C16 C11 C13 107.5(2) . . ?
C16 C11 C12 114.9(2) . . ?
C16 C11 C10 106.1(2) . . ?
C13 C11 C12 112.7(2) . . ?
C13 C11 C10 107.5(2) . . ?
C12 C11 C10 107.8(2) . . ?
C4A C1A C10 113.1(2) . . ?
C1 C1A C4A 120.3(3) . . ?
C1 C1A C10 126.6(3) . . ?
C1A C4A C9 112.7(3) . . ?
C4 C4A C1A 120.2(3) . . ?
C4 C4A C9 127.1(3) . . ?
C5A C8A C10 113.6(3) . . ?
C8 C8A C5A 120.3(3) . . ?
C8 C8A C10 126.0(3) . . ?
C4A C9 C5A 106.8(2) . . ?
C4A C9 C12 107.3(2) . . ?
C5A C9 C12 107.4(2) . . ?
C14 C13 C11 114.3(2) . . ?
C8A C5A C9 112.6(3) . . ?
C5 C5A C8A 120.1(3) . . ?
C5 C5A C9 127.3(3) . . ?
C9 C12 C11 110.4(2) . . ?
C4A C4 C3 119.0(4) . . ?
C1A C10 C11 107.0(2) . . ?
C8A C10 C11 107.4(2) . . ?
C8A C10 C1A 106.9(2) . . ?
C1A C1 C2 118.8(3) . . ?
C7 C8 C8A 118.5(4) . . ?
C6 C5 C5A 119.0(4) . . ?
C2 C3 C4 121.1(4) . . ?
C3 C2 C1 120.7(3) . . ?
C6 C7 C8 120.9(4) . . ?
C7 C6 C5 121.1(4) . . ?
O4 C1' C3' 105.9(4) . . ?
O4 C1' C2' 108.0(4) . . ?
C3' C1' C2' 112.6(5) . . ?
C4' C3' C1' 116.3(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.888
_oxdiff_exptl_absorpt_empirical_full_min 0.519


# start Validation Reply Form
_vrf_PLAT230_pm01as210619r1      
;
PROBLEM: Hirshfeld Test Diff for    C1'      --C3'      .        7.6 s.u.  
RESPONSE: This alert was generated because of disorder 
in this particular part of the molecule.
;
# end Validation Reply Form
