# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2024

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

data_230653lt_auto
_database_code_depnum_ccdc_archive 'CCDC 2323184'
loop_
_audit_author_name
_audit_author_address
'Pei-Lin Chen'
;NTHU
Taiwan
;
_audit_update_record             
;
2024-01-03 deposited with the CCDC.	2024-10-02 downloaded from the CCDC.
;
_audit_creation_date             2023-06-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 O4'
_chemical_formula_sum            'C16 H18 O4'
_chemical_formula_weight         274.30
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.7049(3)
_cell_length_b                   14.6860(3)
_cell_length_c                   8.72913(18)
_cell_angle_alpha                90
_cell_angle_beta                 110.758(2)
_cell_angle_gamma                90
_cell_volume                     1403.13(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5622
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.6280
_cell_measurement_theta_min      4.0270
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.875
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9347
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.910
_diffrn_reflns_theta_min         4.039
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.948
_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 -52.00   0.50    0.06    --  -72.13  91.00-112.00   50
  2  ω    -76.00 -50.00   0.50    0.06    --  -75.32  91.00-112.00   52
  3  ω    -52.00 -19.00   0.50    0.06    --  -59.44  91.00-112.00   66
  4  ω    -92.00 -43.00   0.50    0.06    --  -75.32 111.00  30.00   98
  5  ω     78.00 106.00   0.50    0.06    --   56.25  15.00-180.00   56
  6  ω     47.00  74.00   0.50    0.06    --   56.25  15.00-180.00   54
  7  ω     50.00 133.00   0.50    0.06    --   83.87  15.00-120.00  166
  8  ω     62.00 106.00   0.50    0.06    --   56.25  15.00 -60.00   88
  9  ω     56.00 131.00   0.50    0.06    --   83.87  15.00 -30.00  150
 10  ω     42.00 120.00   0.50    0.06    --   75.94  15.00  90.00  156
 11  ω     56.00  85.00   0.50    0.06    --   83.87 -91.00 133.00   58
 12  ω     38.00  90.00   0.50    0.06    --   75.94-111.00 120.00  104
 13  ω     50.00  75.00   0.50    0.06    --   83.87-111.00  60.00   50
 14  ω     58.00  83.00   0.50    0.06    --   56.25-125.00  30.00   50
 15  ω     21.00  47.00   0.50    0.06    --   56.25-125.00  30.00   52
 16  ω     22.00  48.00   0.50    0.06    --   56.25 -91.00 133.00   52
 17  ω     52.00  91.00   0.50    0.06    --   83.87 -95.00 -60.00   78
 18  ω     46.00  76.00   0.50    0.06    --   75.94 -95.00 -90.00   60
 19  ω     47.00  83.00   0.50    0.06    --   83.87-111.00-150.00   72
 20  ω     34.00  82.00   0.50    0.06    --   75.94 -95.00-150.00   96
 21  ω     28.00  53.00   0.50    0.06    --   69.31 -91.00 133.00   50
 22  ω     48.00  77.00   0.50    0.06    --   75.94 -91.00 133.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0236149000
_diffrn_orient_matrix_UB_12      0.0945550000
_diffrn_orient_matrix_UB_13      -0.0592369000
_diffrn_orient_matrix_UB_21      -0.1386987000
_diffrn_orient_matrix_UB_22      0.0172669000
_diffrn_orient_matrix_UB_23      -0.0730862000
_diffrn_orient_matrix_UB_31      0.0042406000
_diffrn_orient_matrix_UB_32      0.0419583000
_diffrn_orient_matrix_UB_33      0.1637005000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2351
_reflns_number_total             2744
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0016(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   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2744
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.058
_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)+(0.0634P)²+1.1147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1386
_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 Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C)
;
_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
C2 C 0.22985(17) 0.06856(12) 0.5997(2) 0.0231(4) Uani 1 1 d . . . . .
C3 C 0.19656(18) -0.01172(13) 0.6447(2) 0.0267(4) Uani 1 1 d . . . . .
C4 C 0.12538(17) -0.07372(12) 0.5144(2) 0.0244(4) Uani 1 1 d . . . . .
C5 C 0.08683(19) -0.16000(13) 0.5458(2) 0.0289(4) Uani 1 1 d . . . . .
H5 H 0.110643 -0.181286 0.655470 0.035 Uiso 1 1 calc R U . . .
C6 C 0.01459(18) -0.21436(13) 0.4191(2) 0.0289(4) Uani 1 1 d . . . . .
H6 H -0.009453 -0.272959 0.442500 0.035 Uiso 1 1 calc R U . . .
C7 C -0.02314(17) -0.18429(13) 0.2580(2) 0.0256(4) Uani 1 1 d . . . . .
H7 H -0.074997 -0.221259 0.172181 0.031 Uiso 1 1 calc R U . . .
C8 C 0.01492(17) -0.10057(12) 0.2232(2) 0.0242(4) Uani 1 1 d . . . . .
H8 H -0.009187 -0.080121 0.113047 0.029 Uiso 1 1 calc R U . . .
C9 C 0.08924(16) -0.04578(12) 0.3508(2) 0.0219(4) Uani 1 1 d . . . . .
C10 C 0.12530(16) 0.04341(12) 0.3103(2) 0.0231(4) Uani 1 1 d . . . . .
C11 C 0.29979(17) 0.14284(13) 0.7108(2) 0.0251(4) Uani 1 1 d . . . . .
C13 C 0.35543(19) 0.29792(13) 0.7246(3) 0.0314(5) Uani 1 1 d . . . . .
H13A H 0.336126 0.352863 0.656497 0.047 Uiso 1 1 calc R U . . .
H13B H 0.443767 0.287140 0.763941 0.047 Uiso 1 1 calc R U . . .
H13C H 0.328984 0.306049 0.818412 0.047 Uiso 1 1 calc R U . . .
C16 C 0.22234(18) -0.03813(14) 0.8209(2) 0.0299(4) Uani 1 1 d . . . . .
H16A H 0.149491 -0.068708 0.829531 0.036 Uiso 1 1 calc R U . . .
H16B H 0.237665 0.017601 0.888999 0.036 Uiso 1 1 calc R U . . .
C17 C 0.33228(19) -0.10152(15) 0.8871(3) 0.0335(5) Uani 1 1 d . . . . .
H17A H 0.407615 -0.067135 0.898501 0.040 Uiso 1 1 calc R U . . .
H17B H 0.324319 -0.151368 0.807587 0.040 Uiso 1 1 calc R U . . .
C18 C 0.3438(2) -0.14263(15) 1.0541(3) 0.0349(5) Uani 1 1 d . . . . .
H18A H 0.267189 -0.175354 1.042156 0.042 Uiso 1 1 calc R U . . .
H18B H 0.410746 -0.187973 1.085164 0.042 Uiso 1 1 calc R U . . .
C19 C 0.3690(2) -0.07315(15) 1.1934(2) 0.0335(5) Uani 1 1 d . . . . .
H19A H 0.440981 -0.035993 1.199025 0.040 Uiso 1 1 calc R U . . .
H19B H 0.298058 -0.031744 1.169042 0.040 Uiso 1 1 calc R U . . .
C20 C 0.3927(2) -0.11814(18) 1.3589(3) 0.0458(6) Uani 1 1 d . . . . .
H20A H 0.321501 -0.154687 1.354399 0.069 Uiso 1 1 calc R U . . .
H20B H 0.407089 -0.071139 1.443410 0.069 Uiso 1 1 calc R U . . .
H20C H 0.464678 -0.157556 1.385580 0.069 Uiso 1 1 calc R U . . .
O1 O 0.19748(12) 0.09513(8) 0.43812(15) 0.0249(3) Uani 1 1 d . . . . .
O12 O 0.29232(13) 0.22041(9) 0.62819(16) 0.0287(3) Uani 1 1 d . . . . .
O14 O 0.35484(13) 0.13329(9) 0.85513(16) 0.0315(4) Uani 1 1 d . . . . .
O15 O 0.09862(13) 0.07571(9) 0.17459(16) 0.0306(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C3 1.343(3) . ?
C2 C11 1.496(3) . ?
C2 O1 1.381(2) . ?
C3 C4 1.465(3) . ?
C3 C16 1.509(3) . ?
C4 C5 1.404(3) . ?
C4 C9 1.399(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.378(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.399(3) . ?
C9 C10 1.458(2) . ?
C10 O1 1.367(2) . ?
C10 O15 1.210(2) . ?
C11 O12 1.335(2) . ?
C11 O14 1.202(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 O12 1.452(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.526(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.539(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.534(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.522(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C11 126.81(17) . . ?
C3 C2 O1 122.93(17) . . ?
O1 C2 C11 110.20(15) . . ?
C2 C3 C4 117.56(17) . . ?
C2 C3 C16 123.34(17) . . ?
C4 C3 C16 119.00(17) . . ?
C5 C4 C3 122.88(17) . . ?
C9 C4 C3 119.55(17) . . ?
C9 C4 C5 117.52(17) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.81(18) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.76(18) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.71(18) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.73(17) . . ?
C9 C8 H8 120.1 . . ?
C4 C9 C8 121.43(17) . . ?
C4 C9 C10 120.16(16) . . ?
C8 C9 C10 118.37(16) . . ?
O1 C10 C9 116.71(15) . . ?
O15 C10 C9 126.41(17) . . ?
O15 C10 O1 116.87(16) . . ?
O12 C11 C2 110.84(15) . . ?
O14 C11 C2 124.12(17) . . ?
O14 C11 O12 125.04(17) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O12 C13 H13A 109.5 . . ?
O12 C13 H13B 109.5 . . ?
O12 C13 H13C 109.5 . . ?
C3 C16 H16A 109.1 . . ?
C3 C16 H16B 109.1 . . ?
C3 C16 C17 112.32(17) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C16 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C16 C17 C18 112.15(17) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C17 C18 H18A 108.6 . . ?
C17 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 C17 114.70(18) . . ?
C19 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C18 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 C18 112.53(19) . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 O1 C2 122.92(14) . . ?
C11 O12 C13 115.68(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C4 C5 179.02(18) . . . . ?
C2 C3 C4 C9 -3.5(3) . . . . ?
C2 C3 C16 C17 -100.8(2) . . . . ?
C2 C11 O12 C13 179.05(15) . . . . ?
C3 C2 C11 O12 -165.30(18) . . . . ?
C3 C2 C11 O14 14.6(3) . . . . ?
C3 C2 O1 C10 2.3(3) . . . . ?
C3 C4 C5 C6 176.77(18) . . . . ?
C3 C4 C9 C8 -176.05(17) . . . . ?
C3 C4 C9 C10 1.8(3) . . . . ?
C3 C16 C17 C18 -169.21(17) . . . . ?
C4 C3 C16 C17 83.0(2) . . . . ?
C4 C5 C6 C7 -1.1(3) . . . . ?
C4 C9 C10 O1 1.9(2) . . . . ?
C4 C9 C10 O15 -178.94(18) . . . . ?
C5 C4 C9 C8 1.6(3) . . . . ?
C5 C4 C9 C10 179.40(17) . . . . ?
C5 C6 C7 C8 2.1(3) . . . . ?
C6 C7 C8 C9 -1.3(3) . . . . ?
C7 C8 C9 C4 -0.5(3) . . . . ?
C7 C8 C9 C10 -178.42(16) . . . . ?
C8 C9 C10 O1 179.76(15) . . . . ?
C8 C9 C10 O15 -1.0(3) . . . . ?
C9 C4 C5 C6 -0.8(3) . . . . ?
C9 C10 O1 C2 -4.0(2) . . . . ?
C11 C2 C3 C4 178.50(17) . . . . ?
C11 C2 C3 C16 2.2(3) . . . . ?
C11 C2 O1 C10 -175.07(15) . . . . ?
C16 C3 C4 C5 -4.6(3) . . . . ?
C16 C3 C4 C9 172.92(17) . . . . ?
C16 C17 C18 C19 -64.4(2) . . . . ?
C17 C18 C19 C20 -174.06(19) . . . . ?
O1 C2 C3 C4 1.6(3) . . . . ?
O1 C2 C3 C16 -174.69(17) . . . . ?
O1 C2 C11 O12 12.0(2) . . . . ?
O1 C2 C11 O14 -168.17(17) . . . . ?
O14 C11 O12 C13 -0.8(3) . . . . ?
O15 C10 O1 C2 176.74(16) . . . . ?

_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 1.204
_oxdiff_exptl_absorpt_empirical_full_min 0.823
####################################################################### 
# 
# 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_240370lt_auto
_database_code_depnum_ccdc_archive 'CCDC 2343594'
loop_
_audit_author_name
_audit_author_address
'Pei-Lin Chen'
;NTHU
Taiwan
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-10-02 downloaded from the CCDC.
;
_audit_creation_date             2024-03-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H22 O4'
_chemical_formula_sum            'C20 H22 O4'
_chemical_formula_weight         326.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.4776(2)
_cell_length_b                   9.1826(2)
_cell_length_c                   12.9115(3)
_cell_angle_alpha                83.847(2)
_cell_angle_beta                 78.595(2)
_cell_angle_gamma                81.772(2)
_cell_volume                     857.25(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7485
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      72.0950
_cell_measurement_theta_min      3.4880
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10200
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.068
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         3.504
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     59.00 120.00   0.50    0.05    --   69.38  15.00-180.00  122
  2  ω     39.00 117.00   0.50    0.05    --   69.38  15.00 -90.00  156
  3  ω     37.00 106.00   0.50    0.05    --   56.15  15.00  30.00  138
  4  ω     46.00 126.00   0.50    0.05    --   80.61  15.00 -60.00  160
  5  ω     46.00  71.00   0.50    0.05    --   80.61  15.00  30.00   50
  6  ω     74.00 110.00   0.50    0.05    --   80.61  15.00  30.00   72
  7  ω     73.00 121.00   0.50    0.05    --   80.61  15.00  60.00   96
  8  ω     66.00 107.00   0.50    0.05    --   80.61  15.00 150.00   82
  9  ω     39.00  74.00   0.50    0.05    --   80.61-111.00  30.00   70
 10  ω     68.00  93.00   0.50    0.05    --   80.00-105.00-121.25   50
 11  ω     41.00  67.00   0.50    0.05    --   80.00-105.00-121.25   52
 12  ω     60.00  86.00   0.50    0.05    --   80.61-100.00-146.00   52
 13  ω     54.00  80.00   0.50    0.05    --   69.38-100.00-146.00   52
 14  ω     14.00  53.00   0.50    0.05    --   56.15-100.00-146.00   78
 15  ω     39.00  64.00   0.50    0.05    --   80.61 -95.00-120.00   50
 16  ω     40.00  65.00   0.50    0.05    --   80.61 -95.00 -30.00   50
 17  ω     18.00  51.00   0.50    0.05    --   56.15 -95.00  30.00   66
 18  ω     13.00  41.00   0.50    0.05    --   56.15 -95.00  90.00   56
 19  ω     38.00  66.00   0.50    0.05    --   80.61 -95.00  90.00   56
 20  ω     43.00  88.00   0.50    0.05    --   80.61 -95.00  60.00   90
 21  ω     27.00  57.00   0.50    0.05    --   69.38 -95.00 -90.00   60
 22  ω    -56.00 -30.00   0.50    0.05    --  -59.22 100.00 -42.00   52
 23  ω    -97.00 -70.00   0.50    0.05    --  -81.00 114.00-123.49   54
 24  ω    -97.00 -72.00   0.50    0.05    --  -81.00 116.00 -52.33   50
 25  ω    -66.00 -35.00   0.50    0.05    --  -81.00 114.00-123.49   62
 26  ω    -97.00 -35.00   0.50    0.05    --  -81.00 115.00 -17.34  124
 27  ω    -95.00 -36.00   0.50    0.05    --  -81.00 114.00  70.98  118
 28  ω    -97.00 -39.00   0.50    0.05    --  -81.00 116.00 133.85  116
 29  ω    -98.00 -42.00   0.50    0.05    --  -81.00 118.00  98.49  112
 30  ω    -90.00 -50.00   0.50    0.05    --  -76.67 111.00 150.00   80
 31  ω    -92.00 -43.00   0.50    0.05    --  -76.67 111.00  90.00   98
 32  ω    -79.00 -54.00   0.50    0.05    --  -71.82 100.00 -42.00   50
 33  ω    -77.00 -51.00   0.50    0.05    --  -76.67 100.00 -42.00   52
 34  ω    -88.00 -32.00   0.50    0.05    --  -76.67 111.00 -90.00  112
 35  ω   -126.00 -44.00   0.50    0.05    --  -76.67 -15.00  90.00  164
 36  ω   -115.00 -41.00   0.50    0.05    --  -76.67 -15.00   0.00  148
 37  ω   -112.00 -87.00   0.50    0.05    --  -76.67 -15.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1178349000
_diffrn_orient_matrix_UB_12      -0.1516670000
_diffrn_orient_matrix_UB_13      -0.0093659000
_diffrn_orient_matrix_UB_21      -0.0244194000
_diffrn_orient_matrix_UB_22      0.0019977000
_diffrn_orient_matrix_UB_23      -0.1158774000
_diffrn_orient_matrix_UB_31      0.1743382000
_diffrn_orient_matrix_UB_32      0.0769395000
_diffrn_orient_matrix_UB_33      -0.0374070000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2797
_reflns_number_total             3011
_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 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3011
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.069
_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)+(0.0438P)²+0.3614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0943
_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 Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C)
;
_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
O1 O 0.44867(11) 0.47857(9) 0.62625(6) 0.0172(2) Uani 1 1 d . . . . .
O16 O 0.15357(13) 0.11120(10) 0.71891(7) 0.0250(2) Uani 1 1 d . . . . .
O18 O 0.34463(15) 0.23426(11) 0.77891(8) 0.0313(3) Uani 1 1 d . . . . .
O19 O 0.67602(11) 0.52156(10) 0.70436(7) 0.0228(2) Uani 1 1 d . . . . .
C2 C 0.51263(16) 0.52678(13) 0.70669(9) 0.0166(3) Uani 1 1 d . . . . .
C3 C 0.35367(16) 0.58019(13) 0.78659(9) 0.0155(3) Uani 1 1 d . . . . .
C4 C 0.34728(16) 0.63947(13) 0.88469(9) 0.0163(3) Uani 1 1 d . . . . .
C5 C 0.50248(17) 0.66840(15) 0.92240(10) 0.0231(3) Uani 1 1 d . . . . .
H5 H 0.621898 0.647462 0.881179 0.028 Uiso 1 1 calc R U . . .
C6 C 0.48183(19) 0.72653(16) 1.01818(11) 0.0273(3) Uani 1 1 d . . . . .
H6 H 0.587232 0.746697 1.042216 0.033 Uiso 1 1 calc R U . . .
C7 C 0.30660(19) 0.75674(15) 1.08137(10) 0.0253(3) Uani 1 1 d . . . . .
H7 H 0.294282 0.795647 1.148045 0.030 Uiso 1 1 calc R U . . .
C8 C 0.15456(18) 0.73000(15) 1.04662(10) 0.0229(3) Uani 1 1 d . . . . .
H8 H 0.036676 0.750498 1.089662 0.027 Uiso 1 1 calc R U . . .
C9 C 0.16936(17) 0.67218(13) 0.94742(9) 0.0181(3) Uani 1 1 d . . . . .
C10 C 0.01101(17) 0.64703(14) 0.90967(10) 0.0213(3) Uani 1 1 d . . . . .
H10 H -0.106601 0.668161 0.952866 0.026 Uiso 1 1 calc R U . . .
C11 C 0.02193(17) 0.59340(14) 0.81324(10) 0.0192(3) Uani 1 1 d . . . . .
H11 H -0.085487 0.579562 0.788516 0.023 Uiso 1 1 calc R U . . .
C12 C 0.19796(16) 0.55971(13) 0.75239(9) 0.0156(3) Uani 1 1 d . . . . .
C13 C 0.24818(16) 0.49949(13) 0.64524(9) 0.0163(3) Uani 1 1 d . . . . .
C14 C 0.18101(17) 0.35083(13) 0.64119(10) 0.0191(3) Uani 1 1 d . . . . .
H14A H 0.045039 0.365913 0.652083 0.023 Uiso 1 1 calc R U . . .
H14B H 0.227084 0.317201 0.569301 0.023 Uiso 1 1 calc R U . . .
C15 C 0.23840(17) 0.22964(14) 0.72109(9) 0.0193(3) Uani 1 1 d . . . . .
C17 C 0.2012(2) -0.01456(15) 0.79067(11) 0.0295(3) Uani 1 1 d . . . . .
H17A H 0.332207 -0.050539 0.770734 0.044 Uiso 1 1 calc R U . . .
H17B H 0.127924 -0.093330 0.786456 0.044 Uiso 1 1 calc R U . . .
H17C H 0.175808 0.015184 0.863334 0.044 Uiso 1 1 calc R U . . .
C20 C 0.18456(16) 0.60825(14) 0.55655(9) 0.0181(3) Uani 1 1 d . . . . .
H20A H 0.214801 0.558778 0.489692 0.022 Uiso 1 1 calc R U . . .
H20B H 0.049121 0.631456 0.573971 0.022 Uiso 1 1 calc R U . . .
C21 C 0.26855(17) 0.75245(14) 0.53789(10) 0.0208(3) Uani 1 1 d . . . . .
H21A H 0.404054 0.730328 0.528309 0.025 Uiso 1 1 calc R U . . .
H21B H 0.225529 0.809100 0.601129 0.025 Uiso 1 1 calc R U . . .
C22 C 0.21766(17) 0.84645(14) 0.44086(10) 0.0207(3) Uani 1 1 d . . . . .
H22A H 0.082208 0.869620 0.451036 0.025 Uiso 1 1 calc R U . . .
H22B H 0.258781 0.788946 0.377939 0.025 Uiso 1 1 calc R U . . .
C23 C 0.30356(19) 0.99049(14) 0.42017(10) 0.0237(3) Uani 1 1 d . . . . .
H23A H 0.263547 1.047394 0.483444 0.028 Uiso 1 1 calc R U . . .
H23B H 0.439052 0.967210 0.409271 0.028 Uiso 1 1 calc R U . . .
C24 C 0.2514(2) 1.08562(16) 0.32393(12) 0.0314(3) Uani 1 1 d . . . . .
H24A H 0.295740 1.031716 0.260398 0.047 Uiso 1 1 calc R U . . .
H24B H 0.307586 1.177313 0.315362 0.047 Uiso 1 1 calc R U . . .
H24C H 0.117373 1.109046 0.334129 0.047 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
O1 C2 1.3635(14) . ?
O1 C13 1.4583(14) . ?
O16 C15 1.3406(15) . ?
O16 C17 1.4500(15) . ?
O18 C15 1.2005(16) . ?
O19 C2 1.2103(15) . ?
C2 C3 1.4746(16) . ?
C3 C4 1.4211(16) . ?
C3 C12 1.3674(17) . ?
C4 C5 1.4120(17) . ?
C4 C9 1.4240(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3714(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.4075(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.3636(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.4168(17) . ?
C9 C10 1.4226(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.3708(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.4044(17) . ?
C12 C13 1.5033(16) . ?
C13 C14 1.5298(17) . ?
C13 C20 1.5394(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5097(17) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.5217(17) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.5238(17) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.5274(18) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5233(18) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C13 110.95(9) . . ?
C15 O16 C17 115.29(10) . . ?
O1 C2 C3 108.42(10) . . ?
O19 C2 O1 120.89(11) . . ?
O19 C2 C3 130.69(11) . . ?
C4 C3 C2 130.25(11) . . ?
C12 C3 C2 107.57(10) . . ?
C12 C3 C4 122.16(11) . . ?
C3 C4 C9 116.23(11) . . ?
C5 C4 C3 124.79(11) . . ?
C5 C4 C9 118.97(11) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.39(12) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.89(12) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.83(12) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.14(12) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C4 118.76(11) . . ?
C8 C9 C10 121.43(11) . . ?
C10 C9 C4 119.81(11) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 C9 122.40(11) . . ?
C11 C10 H10 118.8 . . ?
C10 C11 H11 121.3 . . ?
C10 C11 C12 117.46(11) . . ?
C12 C11 H11 121.3 . . ?
C3 C12 C11 121.90(11) . . ?
C3 C12 C13 109.89(10) . . ?
C11 C12 C13 128.20(11) . . ?
O1 C13 C12 103.03(9) . . ?
O1 C13 C14 108.59(10) . . ?
O1 C13 C20 108.60(9) . . ?
C12 C13 C14 114.24(10) . . ?
C12 C13 C20 113.15(10) . . ?
C14 C13 C20 108.90(9) . . ?
C13 C14 H14A 108.4 . . ?
C13 C14 H14B 108.4 . . ?
H14A C14 H14B 107.5 . . ?
C15 C14 C13 115.50(10) . . ?
C15 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
O16 C15 C14 110.08(10) . . ?
O18 C15 O16 123.31(12) . . ?
O18 C15 C14 126.62(12) . . ?
O16 C17 H17A 109.5 . . ?
O16 C17 H17B 109.5 . . ?
O16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C20 H20A 108.5 . . ?
C13 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C21 C20 C13 115.04(10) . . ?
C21 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
C20 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
C20 C21 C22 112.13(10) . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C21 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
C21 C22 C23 112.69(10) . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
C22 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 C22 112.89(11) . . ?
C24 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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 C2 C3 C4 179.31(11) . . . . ?
O1 C2 C3 C12 1.13(13) . . . . ?
O1 C13 C14 C15 59.76(13) . . . . ?
O1 C13 C20 C21 -51.71(13) . . . . ?
O19 C2 C3 C4 -0.8(2) . . . . ?
O19 C2 C3 C12 -179.02(13) . . . . ?
C2 O1 C13 C12 -3.13(12) . . . . ?
C2 O1 C13 C14 -124.62(10) . . . . ?
C2 O1 C13 C20 117.10(10) . . . . ?
C2 C3 C4 C5 4.6(2) . . . . ?
C2 C3 C4 C9 -176.01(11) . . . . ?
C2 C3 C12 C11 177.10(11) . . . . ?
C2 C3 C12 C13 -3.13(13) . . . . ?
C3 C4 C5 C6 179.68(12) . . . . ?
C3 C4 C9 C8 179.31(11) . . . . ?
C3 C4 C9 C10 -0.92(17) . . . . ?
C3 C12 C13 O1 3.84(12) . . . . ?
C3 C12 C13 C14 121.42(11) . . . . ?
C3 C12 C13 C20 -113.22(11) . . . . ?
C4 C3 C12 C11 -1.27(18) . . . . ?
C4 C3 C12 C13 178.50(10) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C4 C9 C10 C11 -0.83(19) . . . . ?
C5 C4 C9 C8 -1.23(17) . . . . ?
C5 C4 C9 C10 178.55(11) . . . . ?
C5 C6 C7 C8 -0.9(2) . . . . ?
C6 C7 C8 C9 -0.1(2) . . . . ?
C7 C8 C9 C4 1.15(19) . . . . ?
C7 C8 C9 C10 -178.62(12) . . . . ?
C8 C9 C10 C11 178.94(12) . . . . ?
C9 C4 C5 C6 0.26(19) . . . . ?
C9 C10 C11 C12 1.57(19) . . . . ?
C10 C11 C12 C3 -0.54(18) . . . . ?
C10 C11 C12 C13 179.73(12) . . . . ?
C11 C12 C13 O1 -176.41(11) . . . . ?
C11 C12 C13 C14 -58.83(16) . . . . ?
C11 C12 C13 C20 66.53(15) . . . . ?
C12 C3 C4 C5 -177.48(12) . . . . ?
C12 C3 C4 C9 1.95(17) . . . . ?
C12 C13 C14 C15 -54.59(14) . . . . ?
C12 C13 C20 C21 62.03(13) . . . . ?
C13 O1 C2 O19 -178.46(11) . . . . ?
C13 O1 C2 C3 1.42(13) . . . . ?
C13 C14 C15 O16 172.40(10) . . . . ?
C13 C14 C15 O18 -8.00(19) . . . . ?
C13 C20 C21 C22 173.15(10) . . . . ?
C14 C13 C20 C21 -169.79(10) . . . . ?
C17 O16 C15 O18 -1.09(18) . . . . ?
C17 O16 C15 C14 178.52(11) . . . . ?
C20 C13 C14 C15 177.84(10) . . . . ?
C20 C21 C22 C23 -179.10(10) . . . . ?
C21 C22 C23 C24 -179.38(11) . . . . ?

_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 1.482
_oxdiff_exptl_absorpt_empirical_full_min 0.683
