# Electronic Supplementary Material (ESI) for ChemComm.
# 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_koyama_reduction_auto
_database_code_depnum_ccdc_archive 'CCDC 2324188'
loop_
_audit_author_name
_audit_author_address
'keiji mori'
;tokyo university of agriculture and technology
Japan
;
_audit_update_record             
;
2024-01-09 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_audit_creation_date             2023-09-20
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H26 O4'
_chemical_formula_sum            'C20 H26 O4'
_chemical_formula_weight         330.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H26O4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.10830(10)
_cell_length_b                   14.7871(2)
_cell_length_c                   22.9034(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.1990(10)
_cell_angle_gamma                90
_cell_volume                     3422.68(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7044
_cell_measurement_temperature    100.00(16)
_cell_measurement_theta_max      68.0520
_cell_measurement_theta_min      3.5450
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.816
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.479
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 -4 1 0.0981
-5 5 6 0.1126
1 9 4 0.1780
5 -5 -6 0.1348
0 -9 -5 0.1270
-5 -6 3 0.0968
0 -9 2 0.1147
5 -6 0 0.1388
-1 0 15 0.0474
-1 0 -15 0.0578
-5 -5 6 0.0973
-5 4 -7 0.0854
3 7 -9 0.1310
1 -7 10 0.1114
-6 -5 2 0.0974
0 -9 2 0.1113
1 9 -3 0.1659
-6 -5 -1 0.0979
-2 -8 -7 0.1133
1 -8 -9 0.1276
4 -5 -8 0.1316
1 8 7 0.1710
-5 4 8 0.1081
4 7 -2 0.1458
6 1 4 0.1460
5 6 3 0.1552
4 7 5 0.1505
3 4 -11 0.1178
-3 3 -12 0.0689
0 5 -13 0.0948
2 -1 14 0.0852
3 4 11 0.1234

_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.13
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.9294 -4.0693 1.1389 0.0799 0.1233 0.9891
-5.0135 5.0480 5.7931 -0.4102 -0.6762 0.6119
1.2877 8.9688 4.3531 -0.4724 -0.7702 -0.4286
5.2590 -4.5566 -5.6565 0.3887 0.6414 -0.6614
0.0997 -8.9969 -5.1774 0.5089 0.8315 0.2230
-5.2122 -5.6292 2.5828 0.0042 0.3249 0.9457
0.3714 -9.4693 2.2629 0.0228 0.9659 0.2581
4.9884 -6.2231 0.4064 0.0232 0.8524 -0.5223
-0.8270 -0.1512 14.7835 -0.9623 0.1243 0.2421
-0.5742 -0.4896 -14.7611 0.9914 -0.1290 -0.0202
-4.6940 -5.4453 6.2804 -0.2503 0.3692 0.8950
-5.1359 3.6447 -7.0885 0.4682 -0.6752 0.5700
3.0196 6.5839 -8.5192 0.3991 -0.5838 -0.7071
0.5098 -6.9119 10.2261 -0.5527 0.8031 0.2226
-5.6168 -4.7526 2.4576 0.0015 0.2185 0.9758
0.0025 -9.4777 2.3490 0.0222 0.9498 0.3121
1.2167 9.2896 -2.5801 -0.0197 -0.8750 -0.4837
-5.5523 -5.0839 -0.5615 0.2062 0.2235 0.9527
-1.7776 -8.1814 -6.5610 0.6100 0.6473 0.4570
1.4948 -7.5722 -8.5544 0.6866 0.7254 -0.0491
4.4117 -4.8670 -8.2259 0.5754 0.6050 -0.5503
0.8545 8.2353 7.3432 -0.6503 -0.6892 -0.3195
-4.7036 4.4132 8.0147 -0.5491 -0.5768 0.6048
4.2032 7.2839 -1.9224 -0.0653 -0.5285 -0.8464
6.2663 1.2462 3.6625 -0.3486 0.2172 -0.9118
4.6493 6.4899 2.7677 -0.3661 -0.3820 -0.8485
4.0147 6.8525 4.8644 -0.5029 -0.4269 -0.7516
3.4175 4.3166 -10.9461 0.5965 -0.3676 -0.7135
-3.2768 3.1461 -11.7673 0.7617 -0.5841 0.2803
-0.0439 4.6612 -12.9924 0.7712 -0.5887 -0.2421
1.5240 -1.1695 14.2726 -0.9408 0.3319 -0.0690
3.1835 4.3113 10.9994 -0.8493 -0.1567 -0.5041

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9586
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.214
_diffrn_reflns_theta_min         3.558
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(16)
_diffrn_detector                 'Rigaku HyPix-Bantam area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00 -16.00   0.50    0.20    --  -80.25  42.00 120.00   52
  2  ω    -28.00  23.00   0.50    0.20    --  -42.87  32.00 -30.00  102
  3  ω    -68.00 -16.00   0.50    0.20    --  -80.25  59.00 -60.00  104
  4  ω    -47.00 -14.00   0.50    0.20    --  -80.25  42.00-180.00   66
  5  ω    -28.00  20.00   0.50    0.20    --  -42.87  21.00-150.00   96
  6  ω    -17.00   9.00   0.50    0.20    --  -42.87  11.00-120.00   52
  7  ω    -28.00  21.00   0.50    0.20    --  -42.87  21.00 -90.00   98
  8  ω    -24.00  30.00   0.50    0.20    --  -42.87  11.00 150.00  108
  9  ω    -57.00  19.00   0.50    0.20    --  -42.87 101.00 -48.00  152
 10  ω   -103.00 -64.00   0.50    0.20    --  -42.87-138.00 150.00   78
 11  ω   -149.00-116.00   0.50    0.20    --  -80.25-101.00-152.00   66
 12  ω    -75.00 -47.00   0.50    0.20    --  -80.25 101.00 -48.00   56
 13  ω     26.00  53.00   0.50    0.20    --   42.87-101.00-152.00   54
 14  ω     85.00 122.00   0.50    0.20    --   94.32 -87.00-120.00   74
 15  ω     59.00 106.00   0.50    0.20    --   94.32-101.00-152.00   94
 16  ω     26.00  74.00   0.50    0.20    --   94.32 -87.00-120.00   96
 17  ω     77.00 103.00   0.50    0.20    --   94.32 -96.00 120.00   52
 18  ω     25.00  69.00   0.50    0.20    --   94.32 -96.00 120.00   88
 19  ω     -1.00  24.00   0.50    0.20    --   42.87 -11.00 150.00   50
 20  ω     30.00  61.00   0.50    0.20    --   94.32 -59.00 150.00   62
 21  ω     28.00  53.00   0.50    0.20    --   94.32 -59.00 120.00   50
 22  ω     28.00  53.00   0.50    0.20    --   94.32 -59.00  60.00   50
 23  ω     29.00  61.00   0.50    0.20    --   94.32 -59.00 -60.00   64
 24  ω     29.00  55.00   0.50    0.20    --   94.32 -50.00 -60.00   52
 25  ω     37.00  63.00   0.50    0.20    --   94.32 -59.00 -90.00   52
 26  ω     48.00  80.00   0.50    0.20    --   94.32 -68.00-120.00   64
 27  ω     36.00  61.00   0.50    0.20    --   94.32 -59.00-180.00   50
 28  ω     28.00  53.00   0.50    0.20    --   94.32 -50.00-120.00   50
 29  ω     28.00  53.00   0.50    0.20    --   94.32 -50.00 -30.00   50
 30  ω     28.00  53.00   0.50    0.20    --   94.32 -50.00  30.00   50
 31  ω     28.00  53.00   0.50    0.20    --   94.32 -50.00  60.00   50
 32  ω     28.00  53.00   0.50    0.20    --   94.32 -50.00 120.00   50
 33  ω     28.00  55.00   0.50    0.20    --   94.32 -50.00  90.00   54
 34  ω     88.00 161.00   0.50    0.20    --   94.32  25.00 -30.00  146
 35  ω     82.00 161.00   0.50    0.20    --   94.32  50.00 -90.00  158
 36  ω    120.00 146.00   0.50    0.20    --   94.32 101.00 -48.00   52
 37  ω    101.00 143.00   0.50    0.20    --   94.32 117.00 150.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-i'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0133193000
_diffrn_orient_matrix_UB_12      -0.0187110000
_diffrn_orient_matrix_UB_13      -0.0660272000
_diffrn_orient_matrix_UB_21      0.0481871000
_diffrn_orient_matrix_UB_22      -0.0976954000
_diffrn_orient_matrix_UB_23      0.0101020000
_diffrn_orient_matrix_UB_31      -0.1440151000
_diffrn_orient_matrix_UB_32      -0.0309886000
_diffrn_orient_matrix_UB_33      0.0080009000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-i
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2913
_reflns_number_total             3123
_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 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+2.1700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0899
_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:
 C00H(H00K)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00D(H00D,H00E), C00F(H00G,H00H), C00G(H00I,H00J), C00K(H00P,
 H00Q), C00M(H00S,H00T)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00F), C00I(H00L), C00L(H00R)
2.d Idealised Me refined as rotating group:
 C00J(H00M,H00N,H00O), C00N(H00U,H00V,H00W), C00O(H00X,H00Y,H)
;
_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 0.35482(8) 0.68369(6) 0.68658(4) 0.0201(2) Uani 1 1 d . . . . .
O002 O 0.51516(8) 0.71875(6) 0.75172(3) 0.01827(19) Uani 1 1 d . . . . .
O003 O 0.40020(8) 0.88785(5) 0.72009(4) 0.0191(2) Uani 1 1 d . . . . .
O004 O 0.58921(8) 0.94695(6) 0.68632(4) 0.0218(2) Uani 1 1 d . . . . .
C005 C 0.61400(11) 0.64546(8) 0.59028(5) 0.0150(2) Uani 1 1 d . . . . .
C006 C 0.70176(11) 0.67888(8) 0.63341(5) 0.0151(2) Uani 1 1 d . . . . .
C007 C 0.45423(11) 0.72473(8) 0.69914(5) 0.0152(2) Uani 1 1 d . . . . .
C008 C 0.47889(10) 0.79370(7) 0.59482(5) 0.0138(2) Uani 1 1 d . . . . .
C009 C 0.52947(10) 0.79265(8) 0.66070(5) 0.0141(2) Uani 1 1 d . . . . .
C00A C 0.33288(11) 0.82723(8) 0.59001(5) 0.0170(2) Uani 1 1 d . . . . .
H00A H 0.292577 0.800958 0.554084 0.020 Uiso 1 1 calc R U . . .
H00B H 0.284651 0.802006 0.623486 0.020 Uiso 1 1 calc R U . . .
C00B C 0.51217(11) 0.88524(8) 0.68980(5) 0.0157(2) Uani 1 1 d . . . . .
C00C C 0.81345(11) 0.62849(8) 0.65005(5) 0.0183(3) Uani 1 1 d . . . . .
H00C H 0.872292 0.651699 0.679260 0.022 Uiso 1 1 calc R U . . .
C00D C 0.67744(10) 0.76812(8) 0.66323(5) 0.0150(2) Uani 1 1 d . . . . .
H00D H 0.728877 0.816151 0.643911 0.018 Uiso 1 1 calc R U . . .
H00E H 0.708058 0.764418 0.704502 0.018 Uiso 1 1 calc R U . . .
C00E C 0.64198(12) 0.56064(8) 0.56625(5) 0.0201(3) Uani 1 1 d . . . . .
H00F H 0.582851 0.536122 0.537612 0.024 Uiso 1 1 calc R U . . .
C00F C 0.46049(11) 0.68988(8) 0.50508(5) 0.0179(3) Uani 1 1 d . . . . .
H00G H 0.474427 0.626957 0.491779 0.021 Uiso 1 1 calc R U . . .
H00H H 0.366844 0.705688 0.496689 0.021 Uiso 1 1 calc R U . . .
C00G C 0.56950(11) 0.85408(8) 0.55761(5) 0.0175(2) Uani 1 1 d . . . . .
H00I H 0.561591 0.917531 0.570876 0.021 Uiso 1 1 calc R U . . .
H00J H 0.662571 0.835096 0.564097 0.021 Uiso 1 1 calc R U . . .
C00H C 0.48633(11) 0.69441(7) 0.57178(5) 0.0146(2) Uani 1 1 d . . . . .
H00K H 0.412190 0.660795 0.590199 0.018 Uiso 1 1 calc R U . . .
C00I C 0.84004(12) 0.54568(9) 0.62490(5) 0.0219(3) Uani 1 1 d . . . . .
H00L H 0.916954 0.512608 0.636234 0.026 Uiso 1 1 calc R U . . .
C00J C 0.30840(12) 0.92965(8) 0.58860(6) 0.0234(3) Uani 1 1 d . . . . .
H00M H 0.335762 0.954036 0.550944 0.035 Uiso 1 1 calc R U . . .
H00N H 0.359777 0.958636 0.620167 0.035 Uiso 1 1 calc R U . . .
H00O H 0.214032 0.941670 0.593790 0.035 Uiso 1 1 calc R U . . .
C00K C 0.54855(12) 0.75247(9) 0.47036(5) 0.0215(3) Uani 1 1 d . . . . .
H00P H 0.522678 0.749635 0.428468 0.026 Uiso 1 1 calc R U . . .
H00Q H 0.641774 0.732527 0.474467 0.026 Uiso 1 1 calc R U . . .
C00L C 0.75271(13) 0.51153(9) 0.58283(5) 0.0236(3) Uani 1 1 d . . . . .
H00R H 0.769122 0.454392 0.565450 0.028 Uiso 1 1 calc R U . . .
C00M C 0.53586(12) 0.84944(9) 0.49220(5) 0.0217(3) Uani 1 1 d . . . . .
H00S H 0.444341 0.871204 0.485007 0.026 Uiso 1 1 calc R U . . .
H00T H 0.596625 0.889129 0.470558 0.026 Uiso 1 1 calc R U . . .
C00N C 0.43957(13) 0.67323(9) 0.79601(5) 0.0237(3) Uani 1 1 d . . . . .
H00U H 0.421346 0.610935 0.783668 0.036 Uiso 1 1 calc R U . . .
H00V H 0.355848 0.705278 0.801418 0.036 Uiso 1 1 calc R U . . .
H00W H 0.490381 0.672703 0.832927 0.036 Uiso 1 1 calc R U . . .
C00O C 0.37173(12) 0.97106(9) 0.75089(6) 0.0236(3) Uani 1 1 d . . . . .
H00X H 0.342424 1.017307 0.722831 0.035 Uiso 1 1 calc R U . . .
H00Y H 0.451785 0.991964 0.771653 0.035 Uiso 1 1 calc R U . . .
H H 0.301730 0.960151 0.779007 0.035 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 C007 1.2036(14) . ?
O002 C007 1.3439(14) . ?
O002 C00N 1.4487(14) . ?
O003 C00B 1.3403(14) . ?
O003 C00O 1.4502(14) . ?
O004 C00B 1.2034(14) . ?
C005 C006 1.4037(16) . ?
C005 C00E 1.4008(16) . ?
C005 C00H 1.5318(15) . ?
C006 C00C 1.3989(16) . ?
C006 C00D 1.5084(16) . ?
C007 C009 1.5462(15) . ?
C008 C009 1.5831(15) . ?
C008 C00A 1.5587(15) . ?
C008 C00G 1.5476(15) . ?
C008 C00H 1.5625(15) . ?
C009 C00B 1.5344(15) . ?
C009 C00D 1.5390(15) . ?
C00A C00J 1.5348(16) . ?
C00C C00I 1.3821(17) . ?
C00E C00L 1.3808(17) . ?
C00F C00H 1.5458(15) . ?
C00F C00K 1.5202(17) . ?
C00G C00M 1.5308(16) . ?
C00I C00L 1.3882(18) . ?
C00K C00M 1.5249(18) . ?

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
C007 O002 C00N 114.81(9) . . ?
C00B O003 C00O 117.03(9) . . ?
C006 C005 C00H 123.00(10) . . ?
C00E C005 C006 117.52(10) . . ?
C00E C005 C00H 119.35(10) . . ?
C005 C006 C00D 121.34(10) . . ?
C00C C006 C005 119.91(11) . . ?
C00C C006 C00D 118.74(10) . . ?
O001 C007 O002 123.07(10) . . ?
O001 C007 C009 127.56(10) . . ?
O002 C007 C009 109.35(9) . . ?
C00A C008 C009 110.90(9) . . ?
C00A C008 C00H 109.10(9) . . ?
C00G C008 C009 110.33(9) . . ?
C00G C008 C00A 110.37(9) . . ?
C00G C008 C00H 108.84(9) . . ?
C00H C008 C009 107.21(9) . . ?
C007 C009 C008 113.34(9) . . ?
C00B C009 C007 105.69(9) . . ?
C00B C009 C008 111.59(9) . . ?
C00B C009 C00D 108.27(9) . . ?
C00D C009 C007 108.34(9) . . ?
C00D C009 C008 109.42(9) . . ?
C00J C00A C008 117.86(10) . . ?
O003 C00B C009 110.83(9) . . ?
O004 C00B O003 124.55(10) . . ?
O004 C00B C009 124.62(10) . . ?
C00I C00C C006 121.42(11) . . ?
C006 C00D C009 110.89(9) . . ?
C00L C00E C005 122.14(11) . . ?
C00K C00F C00H 113.70(9) . . ?
C00M C00G C008 113.03(9) . . ?
C005 C00H C008 113.38(9) . . ?
C005 C00H C00F 112.14(9) . . ?
C00F C00H C008 111.48(9) . . ?
C00C C00I C00L 119.03(11) . . ?
C00F C00K C00M 110.29(10) . . ?
C00E C00L C00I 119.97(11) . . ?
C00K C00M C00G 110.16(10) . . ?

_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 1.134
_oxdiff_exptl_absorpt_empirical_full_min 0.824
####################################################################### 
# 
# 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_koyamadiol_auto
_database_code_depnum_ccdc_archive 'CCDC 2338653'
loop_
_audit_author_name
_audit_author_address
'keiji mori'
;tokyo university of agriculture and technology
Japan
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_audit_creation_date             2024-03-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H24 O2'
_chemical_formula_sum            'C18 H24 O2'
_chemical_formula_weight         272.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H24O2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.86400(10)
_cell_length_b                   9.86560(10)
_cell_length_c                   16.5931(2)
_cell_angle_alpha                105.1650(10)
_cell_angle_beta                 97.0650(10)
_cell_angle_gamma                105.2950(10)
_cell_volume                     1470.99(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18573
_cell_measurement_temperature    101(1)
_cell_measurement_theta_max      68.0500
_cell_measurement_theta_min      2.8180
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.888
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -2 -1 0.0946
-1 4 6 0.0673
-6 2 5 0.0784
-5 -1 -3 0.0968
4 1 5 0.0930
-1 -1 11 0.0374
-1 6 1 0.0822
-1 -5 7 0.0799
0 -5 8 0.0684
6 -2 4 0.0882
1 -6 -1 0.0814
5 -5 -1 0.0905
1 0 -10 0.0357
3 0 -10 0.0371
-5 5 -2 0.0959
-1 6 -2 0.0774
1 -3 -8 0.0470
5 -1 -7 0.0476
0 2 -11 0.0289
1 2 -11 0.0274

_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.3993 -2.4995 -1.4213 -0.0726 -0.2877 0.9550
-0.7234 4.1828 5.7049 0.2177 0.9062 -0.3624
-5.7848 2.1245 5.1265 0.1750 0.7449 0.6438
-4.9855 -1.0242 -2.8136 -0.2719 -0.1438 0.9515
4.3298 0.7146 4.9584 0.4442 0.2381 -0.8637
-1.0705 -1.0067 10.7085 0.8775 0.4783 0.0363
-0.7444 5.9130 0.7834 -0.2625 0.8756 -0.4055
-1.1178 -5.2547 7.2800 0.8274 -0.2896 0.4813
0.3821 -5.4101 7.9066 0.9160 -0.3218 0.2395
5.5719 -1.7183 3.9736 0.5191 -0.1865 -0.8341
0.5683 -5.8811 -0.7569 0.2592 -0.8645 0.4306
5.3511 -4.6175 -1.2290 0.2546 -0.8610 -0.4403
1.2934 -0.4022 -10.1972 -0.7588 -0.6502 0.0384
3.0023 0.0739 -9.9523 -0.7290 -0.6230 -0.2835
-5.4023 4.6771 -1.6770 -0.4886 0.7122 0.5040
-1.1088 6.3623 -2.3171 -0.5387 0.7791 -0.3207
1.1322 -2.5064 -8.3892 -0.5091 -0.8352 0.2080
5.0795 -1.0120 -7.3947 -0.4271 -0.6949 -0.5786
0.2639 1.5240 -10.7206 -0.9221 -0.3838 0.0496
1.2638 1.7738 -10.7305 -0.9153 -0.3801 -0.1331

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30651
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.314
_diffrn_reflns_theta_min         2.820
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      101(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00 -40.00   0.50    0.20    --  -42.87 110.00  82.00   52
  2  ω     23.00  48.00   0.50    0.20    --   42.87-110.00 -12.00   50
  3  ω   -124.00 -98.00   0.50    0.52    --  -80.25-110.00 -12.00   52
  4  ω    -82.00 -48.00   0.50    0.52    --  -80.25 110.00  82.00   68
  5  ω     59.00  94.00   0.50    0.52    --   94.32-110.00 -12.00   70
  6  ω    113.00 140.00   0.50    0.52    --   94.32 110.00  82.00   54
  7  ω    -52.00 -12.00   0.50    0.20    --   -8.00 124.00 117.69   80
  8  ω    -47.00  -9.00   0.50    0.20    --   -8.00 119.00  42.34   76
  9  ω    -30.00  -5.00   0.50    0.20    --    8.00 113.00 -35.83   50
 10  ω    -72.00 -24.00   0.50    0.20    --  -12.00 143.00-161.58   96
 11  ω    -13.00  13.00   0.50    0.20    --   20.00 102.00 130.23   52
 12  ω     -5.00  21.00   0.50    0.20    --   24.00  98.00-129.26   52
 13  ω     -4.00  21.00   0.50    0.20    --   28.00  98.00 -75.64   50
 14  ω     -4.00  21.00   0.50    0.20    --   28.00  99.00   9.48   50
 15  ω      0.00  25.00   0.50    0.20    --   32.00  98.00-163.05   50
 16  ω      0.00  25.00   0.50    0.20    --   32.00  98.00 -78.42   50
 17  ω      5.00  30.00   0.50    0.20    --   36.00  94.00  78.50   50
 18  ω      4.00  29.00   0.50    0.20    --   36.00  95.00 -35.96   50
 19  ω      9.00  34.00   0.50    0.20    --   40.00  94.00 111.52   50
 20  ω      9.00  34.00   0.50    0.20    --   40.00  94.00-154.28   50
 21  ω     11.00  38.00   0.50    0.20    --   40.00  88.00   1.46   54
 22  ω     54.00  90.00   0.50    0.20    --   42.87-138.00-180.00   72
 23  ω     15.00  40.00   0.50    0.20    --   44.00  88.00  98.41   50
 24  ω     14.00  39.00   0.50    0.20    --   44.00  91.00 -44.37   50
 25  ω     14.00  39.00   0.50    0.20    --   44.00  92.00  30.33   50
 26  ω     14.00  39.00   0.50    0.20    --   44.00  90.00 154.10   50
 27  ω     14.00  39.00   0.50    0.20    --   44.00  92.00 -97.02   50
 28  ω     14.00  39.00   0.50    0.20    --   44.00  92.00-140.59   50
 29  ω    -72.00 -27.00   0.50    0.20    --  -52.00 -77.00  59.77   90
 30  ω    -54.00 -29.00   0.50    0.20    --  -52.00 -71.00 -17.28   50
 31  ω    -56.00 -29.00   0.50    0.20    --  -52.00 -69.00 140.86   54
 32  ω    -54.00 -28.00   0.50    0.20    --  -52.00 -72.00-117.16   52
 33  ω   -108.00 -82.00   0.50    0.20    --  -52.00 -77.00  59.77   52
 34  ω     27.00  52.00   0.50    0.20    --   52.00  77.00 -82.77   50
 35  ω    -63.00 -37.00   0.50    0.20    --  -56.00 -63.00-166.38   52
 36  ω    -62.00 -33.00   0.50    0.20    --  -56.00 -71.00-130.17   58
 37  ω   -107.00 -81.00   0.50    0.20    --  -56.00 -71.00-130.17   52
 38  ω    -60.00 -34.00   0.50    0.20    --  -56.00 -73.00 104.90   52
 39  ω   -122.00 -91.00   0.50    0.20    --  -56.00 -73.00 130.56   62
 40  ω   -116.00 -91.00   0.50    0.20    --  -56.00 -72.00  25.67   50
 41  ω    -57.00 -32.00   0.50    0.20    --  -56.00 -72.00  25.67   50
 42  ω    -60.00 -32.00   0.50    0.20    --  -56.00 -73.00 130.56   56
 43  ω     31.00  57.00   0.50    0.20    --   56.00  77.00-126.55   52
 44  ω    -67.00 -37.00   0.50    0.20    --  -60.00 -72.00 -64.15   60
 45  ω   -112.00 -87.00   0.50    0.20    --  -60.00 -72.00 -64.15   50
 46  ω   -125.00-100.00   0.50    0.20    --  -60.00 -74.00 -70.73   50
 47  ω    -70.00 -36.00   0.50    0.20    --  -60.00 -74.00 -70.73   68
 48  ω   -106.00 -36.00   0.50    0.20    --  -60.00 -74.00 -15.25  140
 49  ω     40.00  70.00   0.50    0.20    --   64.00  76.00 128.87   60
 50  ω    -71.00 -41.00   0.50    0.20    --  -64.00 -76.00  21.52   60
 51  ω     94.00 128.00   0.50    0.20    --   64.00  76.00 128.87   68
 52  ω    -75.00 -43.00   0.50    0.20    --  -64.00 -69.00 -97.43   64
 53  ω    -65.00 -40.00   0.50    0.20    --  -64.00 -72.00 -41.12   50
 54  ω    -67.00 -40.00   0.50    0.20    --  -64.00 -76.00-153.53   54
 55  ω     47.00  73.00   0.50    0.20    --   68.00  77.00 -92.65   52
 56  ω    -74.00 -48.00   0.50    0.52    --  -72.00 -75.00-172.70   52
 57  ω    -74.00 -48.00   0.50    0.52    --  -72.00 -77.00  -5.53   52
 58  ω    -74.00 -47.00   0.50    0.52    --  -72.00 -77.00 -54.20   54
 59  ω   -119.00 -80.00   0.50    0.52    --  -72.00 -77.00 -54.20   78
 60  ω    -84.00 -47.00   0.50    0.52    --  -72.00 -76.00  13.06   74
 61  ω    -83.00 -51.00   0.50    0.52    --  -76.00 -76.00  39.14   64
 62  ω    -92.00 -51.00   0.50    0.52    --  -76.00 -76.00 126.71   82
 63  ω   -122.00 -96.00   0.50    0.52    --  -76.00 -76.00 126.71   52
 64  ω    -91.00 -51.00   0.50    0.52    --  -76.00 -76.00 148.94   80
 65  ω    -87.00 -52.00   0.50    0.52    --  -76.00 -74.00  51.41   70
 66  ω   -113.00 -55.00   0.50    0.52    --  -80.25 -77.00 120.00  116
 67  ω   -146.00 -56.00   0.50    0.52    --  -80.25 -77.00-180.00  180
 68  ω    -94.00 -55.00   0.50    0.52    --  -80.25 -77.00 -30.00   78
 69  ω    -91.00 -55.00   0.50    0.52    --  -80.25 -76.00 -72.07   72
 70  ω    -92.00 -57.00   0.50    0.52    --  -80.25 -77.00   0.00   70
 71  ω   -142.00-102.00   0.50    0.52    --  -80.25 -77.00   0.00   80
 72  ω    -86.00 -58.00   0.50    0.52    --  -80.25 -68.00  60.00   56
 73  ω    -90.00 -58.00   0.50    0.52    --  -80.25 -75.00  21.28   64
 74  ω    -84.00 -55.00   0.50    0.52    --  -80.25 -77.00 150.00   58
 75  ω   -141.00 -92.00   0.50    0.52    --  -80.25 -77.00-120.00   98
 76  ω    -81.00 -55.00   0.50    0.52    --  -80.25 -77.00-150.00   52
 77  ω   -142.00-116.00   0.50    0.52    --  -80.25 -77.00-150.00   52
 78  ω   -147.00 -55.00   0.50    0.52    --  -80.25 -77.00  90.00  184
 79  ω    -99.00 -55.00   0.50    0.52    --  -80.25 -77.00 -90.00   88
 80  ω    -85.00 -55.00   0.50    0.52    --  -80.25 -77.00-120.00   60
 81  ω   -128.00-102.00   0.50    0.52    --  -80.25 -77.00 -90.00   52
 82  ω     60.00  90.00   0.50    0.52    --   84.00  75.00   9.23   60
 83  ω     30.00  82.00   0.50    0.52    --   94.32 -68.00-120.00  104
 84  ω    108.00 159.00   0.50    0.52    --   94.32  68.00  55.95  102
 85  ω     72.00 104.00   0.50    0.52    --   94.32  68.00  55.95   64
 86  ω    114.00 158.00   0.50    0.52    --   94.32  42.00  90.00   88
 87  ω     35.00  60.00   0.50    0.52    --   94.32-117.00 -90.00   50
 88  ω     75.00 101.00   0.50    0.52    --   94.32  68.00 150.00   52
 89  ω     99.00 142.00   0.50    0.52    --   94.32 117.00-120.00   86
 90  ω     52.00 103.00   0.50    0.52    --   94.32-145.00-180.00  102
 91  ω     70.00 107.00   0.50    0.52    --   94.32  77.00 -90.00   74
 92  ω     70.00  95.00   0.50    0.52    --   94.32  77.00-150.00   50
 93  ω     72.00 157.00   0.50    0.52    --   94.32  77.00 150.00  170
 94  ω     26.00 104.00   0.50    0.52    --   94.32 -77.00   0.00  156
 95  ω     58.00 105.00   0.50    0.52    --   94.32 -96.00 150.00   94
 96  ω     70.00 156.00   0.50    0.52    --   94.32  77.00 120.00  172
 97  ω     72.00 161.00   0.50    0.52    --   94.32  68.00-180.00  178
 98  ω     72.00 115.00   0.50    0.52    --   94.32  77.00  90.00   86
 99  ω     72.00 108.00   0.50    0.52    --   94.32  68.00  30.00   72
100  ω    112.00 155.00   0.50    0.52    --   94.32  42.00  30.00   86
101  ω     36.00  69.00   0.50    0.52    --   94.32-117.00  90.00   66
102  ω    128.00 161.00   0.50    0.52    --   94.32  77.00  30.00   66
103  ω     35.00  80.00   0.50    0.52    --   94.32 -68.00 150.00   90
104  ω     71.00 119.00   0.50    0.52    --   94.32  77.00  30.00   96
105  ω     70.00 101.00   0.50    0.52    --   94.32  77.00 -30.00   62
106  ω    136.00 161.00   0.50    0.52    --   94.32  77.00  60.00   50
107  ω     70.00 112.00   0.50    0.52    --   94.32  77.00  60.00   84
108  ω     82.00 108.00   0.50    0.52    --   94.32-117.00  90.00   52
109  ω     29.00  68.00   0.50    0.52    --   94.32 -59.00 -90.00   78
110  ω     75.00 128.00   0.50    0.52    --   94.32  59.00 120.00  106
111  ω    102.00 155.00   0.50    0.52    --   94.32  68.00 -30.00  106
112  ω     30.00  55.00   0.50    0.52    --   94.32 -50.00   0.00   50
113  ω     31.00  56.00   0.50    0.52    --   94.32 -50.00  60.00   50
114  ω     70.00 134.00   0.50    0.52    --   94.32  77.00-120.00  128
115  ω     85.00 110.00   0.50    0.52    --   94.32-117.00-180.00   50
116  ω     30.00  60.00   0.50    0.52    --   94.32 -59.00  60.00   60
117  ω     72.00  98.00   0.50    0.52    --   94.32  68.00 -30.00   52
118  ω    116.00 154.00   0.50    0.52    --   94.32  77.00-150.00   76
119  ω     33.00  66.00   0.50    0.52    --   94.32-117.00-180.00   66
120  ω     34.00  78.00   0.50    0.52    --   94.32 -68.00-150.00   88
121  ω    104.00 137.00   0.50    0.52    --   94.32 117.00 -30.00   66
122  ω     78.00 136.00   0.50    0.52    --   94.32  59.00-150.00  116
123  ω    122.00 148.00   0.50    0.52    --   94.32  77.00 -60.00   52
124  ω     70.00 120.00   0.50    0.52    --   94.32  77.00 -60.00  100
125  ω    113.00 138.00   0.50    0.52    --   94.32  68.00 150.00   50
126  ω     61.00 108.00   0.50    0.52    --   94.32-117.00  30.00   94
127  ω     82.00 153.00   0.50    0.52    --   94.32  42.00 -60.00  142
128  ω    120.00 153.00   0.50    0.52    --   94.32  59.00-120.00   66
129  ω     79.00 108.00   0.50    0.52    --   94.32  59.00-120.00   58
130  ω     28.00  56.00   0.50    0.52    --   94.32 -50.00 -60.00   56
131  ω     93.00 119.00   0.50    0.52    --   94.32 -87.00-150.00   52
132  ω     30.00  79.00   0.50    0.52    --   94.32 -87.00-150.00   98
133  ω     75.00 154.00   0.50    0.52    --   94.32  68.00   0.00  158
134  ω     77.00 110.00   0.50    0.52    --   94.32-117.00 -90.00   66
135  ω    109.00 155.00   0.50    0.52    --   94.32  96.00 -60.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0206422000
_diffrn_orient_matrix_UB_12      -0.0522667000
_diffrn_orient_matrix_UB_13      0.0790902000
_diffrn_orient_matrix_UB_21      -0.0300927000
_diffrn_orient_matrix_UB_22      0.1370695000
_diffrn_orient_matrix_UB_23      0.0545406000
_diffrn_orient_matrix_UB_31      -0.1614000000
_diffrn_orient_matrix_UB_32      -0.0861329000
_diffrn_orient_matrix_UB_33      -0.0208411000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4831
_reflns_number_total             5350
_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 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         5350
_refine_ls_number_restraints     52
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.026
_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)+(0.0524P)²+0.4879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1024
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H2A-O1
 2 with sigma of 0.02
 O2-C16 \\sim O2A-C16A
 with sigma of 0.02
 O4-C34 \\sim O4A-C34A
 with sigma of 0.02
 C19-C34 \\sim C19-C34A
 with sigma of 0.02
 O2-C1 \\sim O2A-C1
 with sigma of 0.04
 O4-C19 \\sim O4A-C19
 with sigma of 0.04
 C1-C16 \\sim C1-C16A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C19 \\sim C34A \\sim O4A: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
C1 \\sim C16A \\sim O2A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
Uanis(C34A) \\sim Ueq, Uanis(O4A) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
4. Rigid body (RIGU) restrains
 C1, C16A, O2A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C16A)=Sof(H16C)=Sof(H16D)=Sof(O2A)=Sof(H2A)=1-FVAR(1)
 Sof(O2)=Sof(H2)=Sof(C16)=Sof(H16A)=Sof(H16B)=FVAR(1)
 Sof(C34A)=Sof(H34C)=Sof(H34D)=Sof(O4A)=Sof(H4AA)=1-FVAR(2)
 Sof(O4)=Sof(H4)=Sof(C34)=Sof(H34A)=Sof(H34B)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C6(H6), C24(H24)
6.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C32(H32A,H32B), C16(H16A,H16B), C33(H33A,
 H33B), C5(H5A,H5B), C4(H4A,H4B), C3(H3A,H3B), C34(H34A,H34B), C35(H35A,H35B),
 C21(H21A,H21B), C17(H17A,H17B), C23(H23A,H23B), C22(H22A,H22B), C16A(H16C,
 H16D), C34A(H34C,H34D)
6.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C30(H30), C28(H28), C29(H29), C12(H12), C10(H10), C11(H11), C9(H9)
6.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C36(H36A,H36B,H36C)
6.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4), O2A(H2A), O4A(H4AA)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.39888(9) 0.58197(10) 0.52612(5) 0.0279(2) Uani 1 1 d D . . . .
H1 H 0.321415 0.602237 0.520387 0.042 Uiso 1 1 calc R U . . .
O2 O 0.74257(9) 0.67926(10) 0.59814(6) 0.0246(3) Uani 0.937(3) 1 d D . P A 1
H2 H 0.684773 0.605816 0.559868 0.037 Uiso 0.937(3) 1 calc R U P A 1
O3 O 0.12986(10) 0.59171(11) 0.48666(6) 0.0317(2) Uani 1 1 d . . . . .
H3 H 0.090900 0.638741 0.521501 0.048 Uiso 1 1 calc R U . . .
O4 O -0.01589(10) 0.78558(12) 0.53429(6) 0.0283(3) Uani 0.894(3) 1 d D . P B 1
H4 H -0.087624 0.757479 0.555223 0.042 Uiso 0.894(3) 1 calc R U P B 1
C31 C 0.30555(13) 0.81957(13) 0.38019(8) 0.0228(3) Uani 1 1 d . . . . .
C2 C 0.58136(13) 0.71028(13) 0.75720(7) 0.0224(3) Uani 1 1 d . . . . .
C7 C 0.49611(13) 0.72834(13) 0.81477(7) 0.0231(3) Uani 1 1 d . . . . .
C27 C 0.36448(13) 0.74756(13) 0.24201(8) 0.0246(3) Uani 1 1 d . . . . .
H27 H 0.337518 0.716503 0.181515 0.029 Uiso 1 1 calc R U . . .
C25 C 0.10704(13) 0.73259(13) 0.25245(8) 0.0234(3) Uani 1 1 d . . . . .
C26 C 0.26113(13) 0.76818(13) 0.29078(7) 0.0221(3) Uani 1 1 d . . . . .
C8 C 0.36774(13) 0.77580(13) 0.79591(7) 0.0235(3) Uani 1 1 d . . . . .
C13 C 0.35081(13) 0.83091(13) 0.72651(7) 0.0231(3) Uani 1 1 d . . . . .
C30 C 0.44532(14) 0.83810(13) 0.41760(8) 0.0258(3) Uani 1 1 d . . . . .
H30 H 0.473043 0.867882 0.478024 0.031 Uiso 1 1 calc R U . . .
C14 C 0.46868(14) 0.85015(13) 0.67776(8) 0.0239(3) Uani 1 1 d . . . . .
H14A H 0.541452 0.947647 0.706647 0.029 Uiso 1 1 calc R U . . .
H14B H 0.428546 0.849391 0.619889 0.029 Uiso 1 1 calc R U . . .
C19 C 0.05169(13) 0.72999(14) 0.39551(8) 0.0247(3) Uani 1 1 d D U . . .
C15 C 0.43873(13) 0.58016(13) 0.61141(7) 0.0229(3) Uani 1 1 d . . . . .
H15A H 0.485202 0.502455 0.610717 0.028 Uiso 1 1 calc R U . . .
H15B H 0.351169 0.555042 0.634921 0.028 Uiso 1 1 calc R U . . .
C32 C 0.19626(14) 0.85152(14) 0.43193(8) 0.0255(3) Uani 1 1 d . . . . .
H32A H 0.184198 0.947781 0.431365 0.031 Uiso 1 1 calc R U . . .
H32B H 0.230576 0.857911 0.491846 0.031 Uiso 1 1 calc R U . . .
C20 C 0.00666(13) 0.71459(14) 0.30080(8) 0.0250(3) Uani 1 1 d . . . . .
C28 C 0.50531(14) 0.77162(14) 0.28032(8) 0.0274(3) Uani 1 1 d . . . . .
H28 H 0.574234 0.759057 0.246102 0.033 Uiso 1 1 calc R U . . .
C1 C 0.54223(13) 0.72969(13) 0.66979(7) 0.0217(3) Uani 1 1 d D U . . .
C16 C 0.67033(19) 0.7843(2) 0.62896(12) 0.0236(4) Uani 0.937(3) 1 d D . P A 1
H16A H 0.635189 0.816283 0.580793 0.028 Uiso 0.937(3) 1 calc R U P A 1
H16B H 0.741138 0.872160 0.671764 0.028 Uiso 0.937(3) 1 calc R U P A 1
C29 C 0.54575(14) 0.81387(14) 0.36826(8) 0.0273(3) Uani 1 1 d . . . . .
H29 H 0.641155 0.826200 0.394642 0.033 Uiso 1 1 calc R U . . .
C6 C 0.52125(14) 0.69502(14) 0.89900(8) 0.0251(3) Uani 1 1 d . . . . .
H6 H 0.426077 0.635373 0.905027 0.030 Uiso 1 1 calc R U . . .
C12 C 0.22852(14) 0.86965(14) 0.70528(8) 0.0279(3) Uani 1 1 d . . . . .
H12 H 0.217891 0.905267 0.657681 0.033 Uiso 1 1 calc R U . . .
C33 C 0.06832(14) 0.58167(14) 0.40168(8) 0.0270(3) Uani 1 1 d . . . . .
H33A H -0.027123 0.505507 0.383012 0.032 Uiso 1 1 calc R U . . .
H33B H 0.130188 0.550243 0.362643 0.032 Uiso 1 1 calc R U . . .
C5 C 0.62130(15) 0.59999(14) 0.89897(8) 0.0287(3) Uani 1 1 d . . . . .
H5A H 0.652406 0.599548 0.957917 0.034 Uiso 1 1 calc R U . . .
H5B H 0.568802 0.497058 0.863572 0.034 Uiso 1 1 calc R U . . .
C4 C 0.75241(14) 0.65883(15) 0.86403(8) 0.0290(3) Uani 1 1 d . . . . .
H4A H 0.805311 0.761544 0.899625 0.035 Uiso 1 1 calc R U . . .
H4B H 0.817328 0.598110 0.866688 0.035 Uiso 1 1 calc R U . . .
C3 C 0.70851(14) 0.65528(15) 0.77229(8) 0.0269(3) Uani 1 1 d . . . . .
H3A H 0.791188 0.716613 0.756211 0.032 Uiso 1 1 calc R U . . .
H3B H 0.684813 0.552592 0.734566 0.032 Uiso 1 1 calc R U . . .
C34 C -0.0625(3) 0.7678(3) 0.44567(15) 0.0251(6) Uani 0.894(3) 1 d D . P B 1
H34A H -0.077447 0.860185 0.439352 0.030 Uiso 0.894(3) 1 calc R U P B 1
H34B H -0.155039 0.687629 0.422407 0.030 Uiso 0.894(3) 1 calc R U P B 1
C10 C 0.13868(15) 0.80690(16) 0.82224(9) 0.0343(3) Uani 1 1 d . . . . .
H10 H 0.066940 0.799679 0.855589 0.041 Uiso 1 1 calc R U . . .
C35 C 0.10840(15) 0.86149(15) 0.14042(8) 0.0315(3) Uani 1 1 d . . . . .
H35A H 0.046189 0.918086 0.165201 0.038 Uiso 1 1 calc R U . . .
H35B H 0.208905 0.917665 0.170139 0.038 Uiso 1 1 calc R U . . .
C21 C -0.15243(14) 0.66734(16) 0.26334(8) 0.0319(3) Uani 1 1 d . . . . .
H21A H -0.197068 0.730668 0.300818 0.038 Uiso 1 1 calc R U . . .
H21B H -0.196164 0.564456 0.262848 0.038 Uiso 1 1 calc R U . . .
C11 C 0.12196(15) 0.85705(16) 0.75255(9) 0.0331(3) Uani 1 1 d . . . . .
H11 H 0.038281 0.882665 0.737149 0.040 Uiso 1 1 calc R U . . .
C17 C 0.57304(15) 0.83629(14) 0.97621(8) 0.0302(3) Uani 1 1 d . . . . .
H17A H 0.679119 0.875297 0.987240 0.036 Uiso 1 1 calc R U . . .
H17B H 0.533951 0.911943 0.962211 0.036 Uiso 1 1 calc R U . . .
C9 C 0.25992(14) 0.76687(15) 0.84391(8) 0.0297(3) Uani 1 1 d . . . . .
H9 H 0.269954 0.732818 0.892166 0.036 Uiso 1 1 calc R U . . .
C23 C -0.08863(14) 0.61773(15) 0.11988(8) 0.0318(3) Uani 1 1 d . . . . .
H23A H -0.115496 0.619674 0.060808 0.038 Uiso 1 1 calc R U . . .
H23B H -0.100111 0.514039 0.117833 0.038 Uiso 1 1 calc R U . . .
C24 C 0.06821(14) 0.71135(14) 0.15745(8) 0.0268(3) Uani 1 1 d . . . . .
H24 H 0.128852 0.654662 0.129104 0.032 Uiso 1 1 calc R U . . .
C22 C -0.18708(14) 0.67588(16) 0.17333(9) 0.0328(3) Uani 1 1 d . . . . .
H22A H -0.288230 0.616948 0.146652 0.039 Uiso 1 1 calc R U . . .
H22B H -0.175409 0.779678 0.175555 0.039 Uiso 1 1 calc R U . . .
C18 C 0.52755(18) 0.81052(17) 1.05689(8) 0.0374(3) Uani 1 1 d . . . . .
H18A H 0.423010 0.787198 1.049579 0.056 Uiso 1 1 calc R U . . .
H18B H 0.574012 0.899847 1.105449 0.056 Uiso 1 1 calc R U . . .
H18C H 0.556378 0.727960 1.067513 0.056 Uiso 1 1 calc R U . . .
C36 C 0.09394(19) 0.8502(2) 0.04674(10) 0.0501(4) Uani 1 1 d . . . . .
H36A H -0.007016 0.803240 0.017683 0.075 Uiso 1 1 calc R U . . .
H36B H 0.151969 0.790840 0.020933 0.075 Uiso 1 1 calc R U . . .
H36C H 0.127506 0.949354 0.041009 0.075 Uiso 1 1 calc R U . . .
C16A C 0.685(2) 0.748(4) 0.6351(16) 0.023(4) Uani 0.063(3) 1 d D U P A 2
H16C H 0.761544 0.833612 0.675565 0.028 Uiso 0.063(3) 1 calc R U P A 2
H16D H 0.714653 0.658705 0.630617 0.028 Uiso 0.063(3) 1 calc R U P A 2
O2A O 0.6647(18) 0.7698(19) 0.5542(9) 0.039(4) Uani 0.063(3) 1 d D U P A 2
H2A H 0.576468 0.743495 0.533154 0.058 Uiso 0.063(3) 1 calc DR U P A 2
C34A C -0.028(2) 0.806(3) 0.4605(18) 0.048(8) Uani 0.106(3) 1 d D U P B 2
H34C H 0.030565 0.842289 0.519321 0.057 Uiso 0.106(3) 1 calc R U P B 2
H34D H -0.050045 0.889519 0.445533 0.057 Uiso 0.106(3) 1 calc R U P B 2
O4A O -0.1556(13) 0.6893(15) 0.4520(8) 0.070(5) Uani 0.106(3) 1 d D U P B 2
H4AA H -0.185855 0.704822 0.497673 0.105 Uiso 0.106(3) 1 calc R U P B 2


_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 C15 1.4275(14) . ?
O2 C16 1.4301(18) . ?
O3 C33 1.4322(15) . ?
O4 C34 1.436(3) . ?
C31 C26 1.4069(17) . ?
C31 C30 1.3845(18) . ?
C31 C32 1.5047(16) . ?
C2 C7 1.3561(16) . ?
C2 C1 1.5284(16) . ?
C2 C3 1.5109(17) . ?
C7 C8 1.4875(17) . ?
C7 C6 1.5235(16) . ?
C27 C26 1.4007(16) . ?
C27 C28 1.3856(18) . ?
C25 C26 1.4839(17) . ?
C25 C20 1.3537(17) . ?
C25 C24 1.5205(16) . ?
C8 C13 1.4063(17) . ?
C8 C9 1.4033(17) . ?
C13 C14 1.4957(16) . ?
C13 C12 1.3908(18) . ?
C30 C29 1.3895(18) . ?
C14 C1 1.5338(16) . ?
C19 C32 1.5308(18) . ?
C19 C20 1.5355(16) . ?
C19 C33 1.5425(17) . ?
C19 C34 1.546(2) . ?
C19 C34A 1.559(17) . ?
C15 C1 1.5400(17) . ?
C20 C21 1.5129(18) . ?
C28 C29 1.3832(18) . ?
C1 C16 1.5454(19) . ?
C1 C16A 1.566(18) . ?
C6 C5 1.5300(17) . ?
C6 C17 1.5408(17) . ?
C12 C11 1.3858(18) . ?
C5 C4 1.5199(18) . ?
C4 C3 1.5191(17) . ?
C10 C11 1.380(2) . ?
C10 C9 1.3903(19) . ?
C35 C24 1.5388(19) . ?
C35 C36 1.5151(19) . ?
C21 C22 1.5201(18) . ?
C17 C18 1.5244(18) . ?
C23 C24 1.5306(18) . ?
C23 C22 1.5160(19) . ?
C16A O2A 1.413(18) . ?
C34A O4A 1.430(16) . ?

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
C26 C31 C32 117.67(11) . . ?
C30 C31 C26 120.00(11) . . ?
C30 C31 C32 122.32(11) . . ?
C7 C2 C1 120.47(11) . . ?
C7 C2 C3 122.11(11) . . ?
C3 C2 C1 117.12(10) . . ?
C2 C7 C8 120.60(11) . . ?
C2 C7 C6 122.69(11) . . ?
C8 C7 C6 116.65(10) . . ?
C28 C27 C26 121.25(11) . . ?
C26 C25 C24 117.29(10) . . ?
C20 C25 C26 120.21(11) . . ?
C20 C25 C24 122.45(11) . . ?
C31 C26 C25 118.98(10) . . ?
C27 C26 C31 118.03(11) . . ?
C27 C26 C25 122.94(11) . . ?
C13 C8 C7 119.45(11) . . ?
C9 C8 C7 122.99(11) . . ?
C9 C8 C13 117.56(11) . . ?
C8 C13 C14 118.46(11) . . ?
C12 C13 C8 120.47(11) . . ?
C12 C13 C14 121.05(11) . . ?
C31 C30 C29 121.12(11) . . ?
C13 C14 C1 113.08(10) . . ?
C32 C19 C20 108.40(10) . . ?
C32 C19 C33 109.57(10) . . ?
C32 C19 C34 110.33(14) . . ?
C32 C19 C34A 94.5(7) . . ?
C20 C19 C33 108.12(10) . . ?
C20 C19 C34 111.01(13) . . ?
C20 C19 C34A 118.6(13) . . ?
C33 C19 C34 109.35(13) . . ?
C33 C19 C34A 116.4(12) . . ?
O1 C15 C1 112.23(10) . . ?
C31 C32 C19 110.53(10) . . ?
C25 C20 C19 120.12(11) . . ?
C25 C20 C21 122.18(11) . . ?
C21 C20 C19 117.52(10) . . ?
C29 C28 C27 120.15(11) . . ?
C2 C1 C14 109.82(9) . . ?
C2 C1 C15 106.76(9) . . ?
C2 C1 C16 115.60(11) . . ?
C2 C1 C16A 104.4(8) . . ?
C14 C1 C15 110.32(10) . . ?
C14 C1 C16 103.37(11) . . ?
C14 C1 C16A 119.6(11) . . ?
C15 C1 C16 110.95(11) . . ?
C15 C1 C16A 105.1(13) . . ?
O2 C16 C1 115.74(13) . . ?
C28 C29 C30 119.28(12) . . ?
C7 C6 C5 111.97(10) . . ?
C7 C6 C17 112.17(10) . . ?
C5 C6 C17 111.94(11) . . ?
C11 C12 C13 120.96(12) . . ?
O3 C33 C19 112.07(10) . . ?
C4 C5 C6 110.90(10) . . ?
C3 C4 C5 110.74(11) . . ?
C2 C3 C4 113.66(10) . . ?
O4 C34 C19 109.82(16) . . ?
C11 C10 C9 120.38(12) . . ?
C36 C35 C24 114.06(12) . . ?
C20 C21 C22 114.00(11) . . ?
C10 C11 C12 119.31(12) . . ?
C18 C17 C6 112.91(11) . . ?
C10 C9 C8 121.29(12) . . ?
C22 C23 C24 110.67(11) . . ?
C25 C24 C35 110.36(10) . . ?
C25 C24 C23 111.30(10) . . ?
C23 C24 C35 113.90(11) . . ?
C23 C22 C21 110.51(11) . . ?
O2A C16A C1 110.7(15) . . ?
O4A C34A C19 102.7(12) . . ?

_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 1.213
_oxdiff_exptl_absorpt_empirical_full_min 0.870
