# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_Compound_3
_database_code_depnum_ccdc_archive 'CCDC 1954077'
loop_
_audit_author_name
_audit_author_address
'Yasuhide Inokuma'
;Graduate School of Engineering, Hokkaido University
Japan
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-11-26 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 O2'
_chemical_formula_sum            'C14 H16 O2'
_chemical_formula_weight         216.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.8117(5)
_cell_length_b                   5.8923(3)
_cell_length_c                   11.6496(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.722(5)
_cell_angle_gamma                90
_cell_volume                     592.25(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2643
_cell_measurement_theta_min      2.3940
_cell_measurement_theta_max      28.3900

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.75756
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4752
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.862
_diffrn_reflns_theta_max         26.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1219
_reflns_number_gt                1086
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²+0.2214P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1219
_refine_ls_number_parameters     75
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0933
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.69733(12) 0.53678(19) 0.47748(9) 0.0170(3) Uani 1 1 d . . . . .
C2 C 0.52786(12) 0.57286(18) 0.46449(9) 0.0163(3) Uani 1 1 d . . . . .
C3 C 0.40921(12) 0.71811(19) 0.39651(9) 0.0173(3) Uani 1 1 d . . . . .
C4 C 0.25474(12) 0.64257(19) 0.42535(9) 0.0171(3) Uani 1 1 d . . . . .
C5 C 0.43102(14) 0.8849(2) 0.32463(11) 0.0253(3) Uani 1 1 d . . . . .
H1 H 0.532556 0.918875 0.313774 0.030 Uiso 1 1 calc R U . . .
H2 H 0.345073 0.970013 0.284147 0.030 Uiso 1 1 calc R U . . .
C6 C 0.15104(13) 0.5259(2) 0.31950(10) 0.0245(3) Uani 1 1 d . . . . .
H3 H 0.122728 0.635517 0.255459 0.037 Uiso 1 1 calc R U . . .
H4 H 0.056915 0.468929 0.342277 0.037 Uiso 1 1 calc R U . . .
H5 H 0.207467 0.398992 0.293390 0.037 Uiso 1 1 calc R U . . .
C7 C 0.16668(14) 0.8369(2) 0.46994(11) 0.0251(3) Uani 1 1 d . . . . .
H6 H 0.232870 0.907026 0.538545 0.038 Uiso 1 1 calc R U . . .
H7 H 0.072700 0.777204 0.491847 0.038 Uiso 1 1 calc R U . . .
H8 H 0.138146 0.950651 0.407960 0.038 Uiso 1 1 calc R U . . .
O1 O 0.78350(9) 0.62702(14) 0.42217(7) 0.0242(2) 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
C1 O1 1.2138(14) . ?
C1 C2 1.4853(14) . ?
C1 C4 1.5435(15) 3_666 ?
C2 C2 1.352(2) 3_666 ?
C2 C3 1.4547(15) . ?
C3 C5 1.3301(17) . ?
C3 C4 1.5328(15) . ?
C4 C7 1.5317(15) . ?
C4 C6 1.5396(15) . ?

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
O1 C1 C2 127.42(10) . . ?
O1 C1 C4 125.57(10) . 3_666 ?
C2 C1 C4 107.00(9) . 3_666 ?
C2 C2 C3 113.36(12) 3_666 . ?
C2 C2 C1 109.23(12) 3_666 . ?
C3 C2 C1 137.40(10) . . ?
C5 C3 C2 126.69(11) . . ?
C5 C3 C4 126.93(10) . . ?
C2 C3 C4 106.37(9) . . ?
C7 C4 C3 113.01(9) . . ?
C7 C4 C6 110.26(9) . . ?
C3 C4 C6 111.29(9) . . ?
C7 C4 C1 110.18(9) . 3_666 ?
C3 C4 C1 103.69(8) . 3_666 ?
C6 C4 C1 108.13(9) . 3_666 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C2 175.02(12) . . . 3_666 ?
C4 C1 C2 C2 -4.11(15) 3_666 . . 3_666 ?
O1 C1 C2 C3 -4.2(2) . . . . ?
C4 C1 C2 C3 176.65(12) 3_666 . . . ?
C2 C2 C3 C5 176.09(13) 3_666 . . . ?
C1 C2 C3 C5 -4.7(2) . . . . ?
C2 C2 C3 C4 -3.25(15) 3_666 . . . ?
C1 C2 C3 C4 175.98(12) . . . . ?
C5 C3 C4 C7 -54.66(15) . . . . ?
C2 C3 C4 C7 124.68(10) . . . . ?
C5 C3 C4 C6 70.04(15) . . . . ?
C2 C3 C4 C6 -110.63(10) . . . . ?
C5 C3 C4 C1 -173.95(11) . . . 3_666 ?
C2 C3 C4 C1 5.39(11) . . . 3_666 ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_Compound_5
_database_code_depnum_ccdc_archive 'CCDC 1954078'
loop_
_audit_author_name
_audit_author_address
'Yasuhide Inokuma'
;Graduate School of Engineering, Hokkaido University
Japan
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H34 O4'
_chemical_formula_sum            'C28 H34 O4'
_chemical_formula_weight         434.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.6894(4)
_cell_length_b                   5.8144(3)
_cell_length_c                   23.4264(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.837(5)
_cell_angle_gamma                90
_cell_volume                     1166.19(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    7677
_cell_measurement_theta_min      2.6640
_cell_measurement_theta_max      29.0110

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.69741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15983
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.647
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2775
_reflns_number_gt                2397
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1242P)²+2.1589P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2775
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.2395
_refine_ls_wR_factor_gt          0.2267
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.2798(3) 0.6942(5) 0.39103(13) 0.0184(6) Uani 1 1 d . . . . .
C2 C 0.2430(3) 0.5176(5) 0.34075(12) 0.0186(6) Uani 1 1 d . . . . .
C3 C 0.4037(3) 0.4535(5) 0.32782(12) 0.0185(6) Uani 1 1 d . . . . .
C4 C 0.5136(3) 0.5812(5) 0.36077(12) 0.0170(6) Uani 1 1 d . . . . .
C5 C 0.6836(3) 0.6239(5) 0.36855(12) 0.0175(6) Uani 1 1 d . . . . .
C6 C 0.7211(3) 0.8052(5) 0.41743(12) 0.0177(6) Uani 1 1 d . . . . .
C7 C 0.5614(3) 0.8669(5) 0.43181(12) 0.0170(6) Uani 1 1 d . . . . .
C8 C 0.4510(3) 0.7356(5) 0.39991(12) 0.0171(6) Uani 1 1 d . . . . .
C9 C 0.1532(4) 0.3117(5) 0.35976(14) 0.0241(7) Uani 1 1 d . . . . .
H1 H 0.128165 0.203431 0.327438 0.036 Uiso 1 1 calc R U . . .
H2 H 0.056354 0.365787 0.371407 0.036 Uiso 1 1 calc R U . . .
H3 H 0.217845 0.234366 0.392565 0.036 Uiso 1 1 calc R U . . .
C10 C 0.1436(4) 0.6390(6) 0.28858(14) 0.0252(7) Uani 1 1 d . . . . .
H4 H 0.199879 0.774113 0.277892 0.038 Uiso 1 1 calc R U . . .
H5 H 0.044017 0.687516 0.298999 0.038 Uiso 1 1 calc R U . . .
H6 H 0.123823 0.532629 0.255702 0.038 Uiso 1 1 calc R U . . .
C11 C 0.4263(4) 0.2754(6) 0.28443(14) 0.0271(7) Uani 1 1 d . . . . .
H7 H 0.534443 0.280173 0.277655 0.041 Uiso 1 1 calc R U . . .
H8 H 0.355173 0.305571 0.248009 0.041 Uiso 1 1 calc R U . . .
H9 H 0.404094 0.123197 0.299048 0.041 Uiso 1 1 calc R U . . .
C12 C 0.8045(4) 1.0114(5) 0.39565(14) 0.0232(6) Uani 1 1 d . . . . .
H10 H 0.737610 1.078989 0.361894 0.035 Uiso 1 1 calc R U . . .
H11 H 0.902874 0.960344 0.384676 0.035 Uiso 1 1 calc R U . . .
H12 H 0.826278 1.126822 0.426467 0.035 Uiso 1 1 calc R U . . .
C13 C 0.8266(4) 0.6943(6) 0.46951(13) 0.0249(7) Uani 1 1 d . . . . .
H13 H 0.845855 0.804774 0.501529 0.037 Uiso 1 1 calc R U . . .
H14 H 0.926114 0.649739 0.458390 0.037 Uiso 1 1 calc R U . . .
H15 H 0.774930 0.557594 0.481836 0.037 Uiso 1 1 calc R U . . .
C14 C 0.5417(4) 1.0457(5) 0.47606(12) 0.0207(6) Uani 1 1 d . . . . .
H16 H 0.481262 1.176208 0.456466 0.025 Uiso 1 1 calc R U . . .
H17 H 0.645900 1.104386 0.493811 0.025 Uiso 1 1 calc R U . . .
O1 O 0.1836(2) 0.7765(4) 0.41697(10) 0.0244(5) Uani 1 1 d . . . . .
O2 O 0.7780(2) 0.5419(4) 0.34154(9) 0.0238(5) 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
C1 O1 1.213(4) . ?
C1 C8 1.486(4) . ?
C1 C2 1.554(4) . ?
C2 C3 1.525(4) . ?
C2 C9 1.536(4) . ?
C2 C10 1.542(4) . ?
C3 C4 1.344(4) . ?
C3 C11 1.487(4) . ?
C4 C8 1.453(4) . ?
C4 C5 1.478(4) . ?
C5 O2 1.216(4) . ?
C5 C6 1.549(4) . ?
C6 C7 1.525(4) . ?
C6 C12 1.533(4) . ?
C6 C13 1.537(4) . ?
C7 C8 1.348(4) . ?
C7 C14 1.498(4) . ?
C9 H1 0.9800 . ?
C9 H2 0.9800 . ?
C9 H3 0.9800 . ?
C10 H4 0.9800 . ?
C10 H5 0.9800 . ?
C10 H6 0.9800 . ?
C11 H7 0.9800 . ?
C11 H8 0.9800 . ?
C11 H9 0.9800 . ?
C12 H10 0.9800 . ?
C12 H11 0.9800 . ?
C12 H12 0.9800 . ?
C13 H13 0.9800 . ?
C13 H14 0.9800 . ?
C13 H15 0.9800 . ?
C14 C14 1.531(6) 3_676 ?
C14 H16 0.9900 . ?
C14 H17 0.9900 . ?

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
O1 C1 C8 128.7(3) . . ?
O1 C1 C2 124.8(3) . . ?
C8 C1 C2 106.5(2) . . ?
C3 C2 C9 113.3(2) . . ?
C3 C2 C10 111.2(2) . . ?
C9 C2 C10 110.1(2) . . ?
C3 C2 C1 103.6(2) . . ?
C9 C2 C1 110.1(2) . . ?
C10 C2 C1 108.2(2) . . ?
C4 C3 C11 127.8(3) . . ?
C4 C3 C2 109.6(2) . . ?
C11 C3 C2 122.6(3) . . ?
C3 C4 C8 113.5(2) . . ?
C3 C4 C5 139.5(3) . . ?
C8 C4 C5 107.0(2) . . ?
O2 C5 C4 128.2(3) . . ?
O2 C5 C6 125.2(3) . . ?
C4 C5 C6 106.6(2) . . ?
C7 C6 C12 112.9(2) . . ?
C7 C6 C13 111.4(2) . . ?
C12 C6 C13 109.9(2) . . ?
C7 C6 C5 103.8(2) . . ?
C12 C6 C5 109.8(2) . . ?
C13 C6 C5 108.8(2) . . ?
C8 C7 C14 128.4(3) . . ?
C8 C7 C6 109.4(2) . . ?
C14 C7 C6 122.1(2) . . ?
C7 C8 C4 113.1(2) . . ?
C7 C8 C1 140.4(3) . . ?
C4 C8 C1 106.5(2) . . ?
C2 C9 H1 109.5 . . ?
C2 C9 H2 109.5 . . ?
H1 C9 H2 109.5 . . ?
C2 C9 H3 109.5 . . ?
H1 C9 H3 109.5 . . ?
H2 C9 H3 109.5 . . ?
C2 C10 H4 109.5 . . ?
C2 C10 H5 109.5 . . ?
H4 C10 H5 109.5 . . ?
C2 C10 H6 109.5 . . ?
H4 C10 H6 109.5 . . ?
H5 C10 H6 109.5 . . ?
C3 C11 H7 109.5 . . ?
C3 C11 H8 109.5 . . ?
H7 C11 H8 109.5 . . ?
C3 C11 H9 109.5 . . ?
H7 C11 H9 109.5 . . ?
H8 C11 H9 109.5 . . ?
C6 C12 H10 109.5 . . ?
C6 C12 H11 109.5 . . ?
H10 C12 H11 109.5 . . ?
C6 C12 H12 109.5 . . ?
H10 C12 H12 109.5 . . ?
H11 C12 H12 109.5 . . ?
C6 C13 H13 109.5 . . ?
C6 C13 H14 109.5 . . ?
H13 C13 H14 109.5 . . ?
C6 C13 H15 109.5 . . ?
H13 C13 H15 109.5 . . ?
H14 C13 H15 109.5 . . ?
C7 C14 C14 113.0(3) . 3_676 ?
C7 C14 H16 109.0 . . ?
C14 C14 H16 109.0 3_676 . ?
C7 C14 H17 109.0 . . ?
C14 C14 H17 109.0 3_676 . ?
H16 C14 H17 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -174.7(3) . . . . ?
C8 C1 C2 C3 4.9(3) . . . . ?
O1 C1 C2 C9 -53.2(4) . . . . ?
C8 C1 C2 C9 126.4(3) . . . . ?
O1 C1 C2 C10 67.2(4) . . . . ?
C8 C1 C2 C10 -113.3(3) . . . . ?
C9 C2 C3 C4 -123.5(3) . . . . ?
C10 C2 C3 C4 111.9(3) . . . . ?
C1 C2 C3 C4 -4.2(3) . . . . ?
C9 C2 C3 C11 56.8(4) . . . . ?
C10 C2 C3 C11 -67.8(4) . . . . ?
C1 C2 C3 C11 176.1(3) . . . . ?
C11 C3 C4 C8 -178.5(3) . . . . ?
C2 C3 C4 C8 1.8(4) . . . . ?
C11 C3 C4 C5 5.1(6) . . . . ?
C2 C3 C4 C5 -174.6(3) . . . . ?
C3 C4 C5 O2 1.7(6) . . . . ?
C8 C4 C5 O2 -174.8(3) . . . . ?
C3 C4 C5 C6 179.5(4) . . . . ?
C8 C4 C5 C6 3.0(3) . . . . ?
O2 C5 C6 C7 174.2(3) . . . . ?
C4 C5 C6 C7 -3.7(3) . . . . ?
O2 C5 C6 C12 53.2(4) . . . . ?
C4 C5 C6 C12 -124.7(2) . . . . ?
O2 C5 C6 C13 -67.1(4) . . . . ?
C4 C5 C6 C13 115.0(3) . . . . ?
C12 C6 C7 C8 122.1(3) . . . . ?
C13 C6 C7 C8 -113.7(3) . . . . ?
C5 C6 C7 C8 3.3(3) . . . . ?
C12 C6 C7 C14 -58.9(4) . . . . ?
C13 C6 C7 C14 65.3(4) . . . . ?
C5 C6 C7 C14 -177.7(2) . . . . ?
C14 C7 C8 C4 179.5(3) . . . . ?
C6 C7 C8 C4 -1.6(3) . . . . ?
C14 C7 C8 C1 -0.5(6) . . . . ?
C6 C7 C8 C1 178.4(3) . . . . ?
C3 C4 C8 C7 -178.5(3) . . . . ?
C5 C4 C8 C7 -1.0(3) . . . . ?
C3 C4 C8 C1 1.5(3) . . . . ?
C5 C4 C8 C1 179.1(2) . . . . ?
O1 C1 C8 C7 -4.5(6) . . . . ?
C2 C1 C8 C7 176.0(4) . . . . ?
O1 C1 C8 C4 175.5(3) . . . . ?
C2 C1 C8 C4 -4.0(3) . . . . ?
C8 C7 C14 C14 54.9(5) . . . 3_676 ?
C6 C7 C14 C14 -123.9(3) . . . 3_676 ?

_refine_diff_density_max         0.553
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.107

####################################################################### 
# 
# 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_Compound_6
_database_code_depnum_ccdc_archive 'CCDC 1954079'
loop_
_audit_author_name
_audit_author_address
'Yasuhide Inokuma'
;Graduate School of Engineering, Hokkaido University
Japan
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H30 O4'
_chemical_formula_sum            'C28 H30 O4'
_chemical_formula_weight         430.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.7961(6)
_cell_length_b                   5.8385(4)
_cell_length_c                   22.8947(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.317(6)
_cell_angle_gamma                90
_cell_volume                     1160.27(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3082
_cell_measurement_theta_min      3.5670
_cell_measurement_theta_max      28.7300

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.77501
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7069
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.647
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2191
_reflns_number_gt                1718
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0878P)²+2.6245P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2191
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0814
_refine_ls_wR_factor_ref         0.2250
_refine_ls_wR_factor_gt          0.2146
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.6838(4) 0.6130(6) 0.36861(14) 0.0184(8) Uani 1 1 d . . . . .
C2 C 0.7273(4) 0.7829(6) 0.42012(15) 0.0212(8) Uani 1 1 d . . . . .
C3 C 0.5750(4) 0.8349(6) 0.44034(16) 0.0232(9) Uani 1 1 d . . . . .
C4 C 0.4560(4) 0.7046(6) 0.40215(15) 0.0207(8) Uani 1 1 d . . . . .
C5 C 0.2867(4) 0.6690(6) 0.39299(15) 0.0212(8) Uani 1 1 d . . . . .
C6 C 0.2462(4) 0.5019(7) 0.33981(15) 0.0224(8) Uani 1 1 d . . . . .
C7 C 0.4037(4) 0.4396(6) 0.32460(15) 0.0206(8) Uani 1 1 d . . . . .
C8 C 0.5160(4) 0.5755(6) 0.36221(14) 0.0179(8) Uani 1 1 d . . . . .
C9 C 0.8425(5) 0.6643(8) 0.46870(16) 0.0318(10) Uani 1 1 d . . . . .
H1 H 0.871563 0.770209 0.501836 0.048 Uiso 1 1 calc R U . . .
H2 H 0.934690 0.619664 0.452478 0.048 Uiso 1 1 calc R U . . .
H3 H 0.794577 0.527621 0.482663 0.048 Uiso 1 1 calc R U . . .
C10 C 0.8010(5) 0.9957(7) 0.39742(19) 0.0323(10) Uani 1 1 d . . . . .
H4 H 0.729079 1.064568 0.365003 0.048 Uiso 1 1 calc R U . . .
H5 H 0.895958 0.951978 0.383041 0.048 Uiso 1 1 calc R U . . .
H6 H 0.825088 1.106830 0.429668 0.048 Uiso 1 1 calc R U . . .
C11 C 0.5668(5) 0.9749(7) 0.48784(17) 0.0289(9) Uani 1 1 d . . . . .
H7 H 0.660050 1.044649 0.506107 0.035 Uiso 1 1 calc R U . . .
C12 C 0.1593(5) 0.2948(7) 0.35933(19) 0.0316(10) Uani 1 1 d . . . . .
H8 H 0.135605 0.187276 0.326243 0.047 Uiso 1 1 calc R U . . .
H9 H 0.063291 0.346610 0.371577 0.047 Uiso 1 1 calc R U . . .
H10 H 0.223603 0.218388 0.392626 0.047 Uiso 1 1 calc R U . . .
C13 C 0.1468(5) 0.6297(8) 0.28905(18) 0.0319(10) Uani 1 1 d . . . . .
H11 H 0.201641 0.766727 0.279045 0.048 Uiso 1 1 calc R U . . .
H12 H 0.049355 0.674874 0.301257 0.048 Uiso 1 1 calc R U . . .
H13 H 0.125877 0.529433 0.254357 0.048 Uiso 1 1 calc R U . . .
C14 C 0.4310(5) 0.2851(7) 0.28394(16) 0.0286(9) Uani 1 1 d . . . . .
H14 H 0.533563 0.256715 0.277769 0.034 Uiso 1 1 calc R U . . .
H15 H 0.347712 0.204497 0.261394 0.034 Uiso 1 1 calc R U . . .
O1 O 0.7728(3) 0.5318(5) 0.33884(11) 0.0264(7) Uani 1 1 d . . . . .
O2 O 0.1917(3) 0.7528(5) 0.41988(12) 0.0307(7) 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
C1 O1 1.215(4) . ?
C1 C8 1.476(5) . ?
C1 C2 1.541(5) . ?
C2 C3 1.518(5) . ?
C2 C10 1.531(5) . ?
C2 C9 1.542(5) . ?
C3 C11 1.371(5) . ?
C3 C4 1.463(5) . ?
C4 C8 1.356(5) . ?
C4 C5 1.485(5) . ?
C5 O2 1.218(4) . ?
C5 C6 1.556(5) . ?
C6 C7 1.526(5) . ?
C6 C13 1.531(5) . ?
C6 C12 1.535(5) . ?
C7 C14 1.345(5) . ?
C7 C8 1.439(5) . ?
C9 H1 0.9800 . ?
C9 H2 0.9800 . ?
C9 H3 0.9800 . ?
C10 H4 0.9800 . ?
C10 H5 0.9800 . ?
C10 H6 0.9800 . ?
C11 C11 1.410(8) 3_676 ?
C11 H7 0.9500 . ?
C12 H8 0.9800 . ?
C12 H9 0.9800 . ?
C12 H10 0.9800 . ?
C13 H11 0.9800 . ?
C13 H12 0.9800 . ?
C13 H13 0.9800 . ?
C14 H14 0.9500 . ?
C14 H15 0.9500 . ?

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
O1 C1 C8 127.7(3) . . ?
O1 C1 C2 125.3(3) . . ?
C8 C1 C2 107.0(3) . . ?
C3 C2 C10 112.6(3) . . ?
C3 C2 C1 103.9(3) . . ?
C10 C2 C1 109.2(3) . . ?
C3 C2 C9 112.3(3) . . ?
C10 C2 C9 110.1(3) . . ?
C1 C2 C9 108.4(3) . . ?
C11 C3 C4 131.3(4) . . ?
C11 C3 C2 121.6(3) . . ?
C4 C3 C2 107.1(3) . . ?
C8 C4 C3 111.9(3) . . ?
C8 C4 C5 108.5(3) . . ?
C3 C4 C5 139.5(3) . . ?
O2 C5 C4 128.8(3) . . ?
O2 C5 C6 123.9(3) . . ?
C4 C5 C6 107.2(3) . . ?
C7 C6 C13 111.8(3) . . ?
C7 C6 C12 113.1(3) . . ?
C13 C6 C12 110.8(3) . . ?
C7 C6 C5 103.1(3) . . ?
C13 C6 C5 108.6(3) . . ?
C12 C6 C5 109.1(3) . . ?
C14 C7 C8 127.0(3) . . ?
C14 C7 C6 126.0(3) . . ?
C8 C7 C6 107.0(3) . . ?
C4 C8 C7 114.0(3) . . ?
C4 C8 C1 110.0(3) . . ?
C7 C8 C1 136.0(3) . . ?
C2 C9 H1 109.5 . . ?
C2 C9 H2 109.5 . . ?
H1 C9 H2 109.5 . . ?
C2 C9 H3 109.5 . . ?
H1 C9 H3 109.5 . . ?
H2 C9 H3 109.5 . . ?
C2 C10 H4 109.5 . . ?
C2 C10 H5 109.5 . . ?
H4 C10 H5 109.5 . . ?
C2 C10 H6 109.5 . . ?
H4 C10 H6 109.5 . . ?
H5 C10 H6 109.5 . . ?
C3 C11 C11 126.2(5) . 3_676 ?
C3 C11 H7 116.9 . . ?
C11 C11 H7 116.9 3_676 . ?
C6 C12 H8 109.5 . . ?
C6 C12 H9 109.5 . . ?
H8 C12 H9 109.5 . . ?
C6 C12 H10 109.5 . . ?
H8 C12 H10 109.5 . . ?
H9 C12 H10 109.5 . . ?
C6 C13 H11 109.5 . . ?
C6 C13 H12 109.5 . . ?
H11 C13 H12 109.5 . . ?
C6 C13 H13 109.5 . . ?
H11 C13 H13 109.5 . . ?
H12 C13 H13 109.5 . . ?
C7 C14 H14 120.0 . . ?
C7 C14 H15 120.0 . . ?
H14 C14 H15 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 178.2(3) . . . . ?
C8 C1 C2 C3 -0.4(4) . . . . ?
O1 C1 C2 C10 57.8(5) . . . . ?
C8 C1 C2 C10 -120.8(3) . . . . ?
O1 C1 C2 C9 -62.2(5) . . . . ?
C8 C1 C2 C9 119.2(3) . . . . ?
C10 C2 C3 C11 -64.7(5) . . . . ?
C1 C2 C3 C11 177.3(3) . . . . ?
C9 C2 C3 C11 60.3(5) . . . . ?
C10 C2 C3 C4 117.5(3) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C9 C2 C3 C4 -117.5(3) . . . . ?
C11 C3 C4 C8 -176.0(4) . . . . ?
C2 C3 C4 C8 1.5(4) . . . . ?
C11 C3 C4 C5 4.3(8) . . . . ?
C2 C3 C4 C5 -178.2(4) . . . . ?
C8 C4 C5 O2 179.6(4) . . . . ?
C3 C4 C5 O2 -0.7(7) . . . . ?
C8 C4 C5 C6 -1.5(4) . . . . ?
C3 C4 C5 C6 178.2(4) . . . . ?
O2 C5 C6 C7 -177.3(3) . . . . ?
C4 C5 C6 C7 3.8(4) . . . . ?
O2 C5 C6 C13 64.0(4) . . . . ?
C4 C5 C6 C13 -114.9(3) . . . . ?
O2 C5 C6 C12 -56.8(5) . . . . ?
C4 C5 C6 C12 124.2(3) . . . . ?
C13 C6 C7 C14 -68.7(5) . . . . ?
C12 C6 C7 C14 57.1(5) . . . . ?
C5 C6 C7 C14 174.8(4) . . . . ?
C13 C6 C7 C8 111.8(3) . . . . ?
C12 C6 C7 C8 -122.4(3) . . . . ?
C5 C6 C7 C8 -4.7(4) . . . . ?
C3 C4 C8 C7 178.5(3) . . . . ?
C5 C4 C8 C7 -1.7(4) . . . . ?
C3 C4 C8 C1 -1.8(4) . . . . ?
C5 C4 C8 C1 178.0(3) . . . . ?
C14 C7 C8 C4 -175.3(4) . . . . ?
C6 C7 C8 C4 4.2(4) . . . . ?
C14 C7 C8 C1 5.2(7) . . . . ?
C6 C7 C8 C1 -175.3(4) . . . . ?
O1 C1 C8 C4 -177.2(4) . . . . ?
C2 C1 C8 C4 1.4(4) . . . . ?
O1 C1 C8 C7 2.4(7) . . . . ?
C2 C1 C8 C7 -179.0(4) . . . . ?
C4 C3 C11 C11 0.7(9) . . . 3_676 ?
C2 C3 C11 C11 -176.5(5) . . . 3_676 ?

_refine_diff_density_max         0.672
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.102

####################################################################### 
# 
# 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_Compound_7
_database_code_depnum_ccdc_archive 'CCDC 1954080'
loop_
_audit_author_name
_audit_author_address
'Yasuhide Inokuma'
;Graduate School of Engineering, Hokkaido University
Japan
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H30 O4'
_chemical_formula_sum            'C28 H30 O4'
_chemical_formula_weight         430.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.6447(4)
_cell_length_b                   17.9325(5)
_cell_length_c                   10.8014(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.228(3)
_cell_angle_gamma                90
_cell_volume                     2384.24(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    18649
_cell_measurement_theta_min      2.5070
_cell_measurement_theta_max      29.3670

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.680
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63387
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36065
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.245
_diffrn_reflns_theta_max         26.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4934
_reflns_number_gt                4438
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²+0.9047P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4934
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.28699(9) 0.39178(7) 0.06750(11) 0.0223(2) Uani 1 1 d . . . . .
C2 C 0.26283(9) 0.46762(7) -0.00045(11) 0.0229(2) Uani 1 1 d . . . . .
C3 C 0.35157(9) 0.51848(7) 0.07308(11) 0.0228(2) Uani 1 1 d . . . . .
C4 C 0.41183(9) 0.47490(6) 0.17889(11) 0.0199(2) Uani 1 1 d . . . . .
C5 C 0.49881(9) 0.49157(6) 0.29126(11) 0.0203(2) Uani 1 1 d . . . . .
C6 C 0.52683(9) 0.41657(6) 0.36193(11) 0.0198(2) Uani 1 1 d . . . . .
H1 H 0.527932 0.421683 0.454411 0.024 Uiso 1 1 calc R U . . .
C7 C 0.43629(9) 0.36344(6) 0.29548(11) 0.0202(2) Uani 1 1 d . . . . .
C8 C 0.37750(9) 0.40340(6) 0.18255(10) 0.0193(2) Uani 1 1 d . . . . .
C9 C 0.26516(13) 0.45944(8) -0.14062(12) 0.0367(3) Uani 1 1 d . . . . .
H2 H 0.250351 0.507876 -0.183055 0.055 Uiso 1 1 calc R U . . .
H3 H 0.209673 0.423458 -0.181295 0.055 Uiso 1 1 calc R U . . .
H4 H 0.336931 0.441726 -0.147407 0.055 Uiso 1 1 calc R U . . .
C10 C 0.14950(10) 0.49333(8) 0.01175(13) 0.0327(3) Uani 1 1 d . . . . .
H5 H 0.147949 0.496543 0.101891 0.049 Uiso 1 1 calc R U . . .
H6 H 0.094812 0.457370 -0.030896 0.049 Uiso 1 1 calc R U . . .
H7 H 0.133599 0.542430 -0.027970 0.049 Uiso 1 1 calc R U . . .
C11 C 0.36996(11) 0.58926(8) 0.04889(13) 0.0343(3) Uani 1 1 d . . . . .
H8 H 0.427071 0.615848 0.103581 0.041 Uiso 1 1 calc R U . . .
H9 H 0.326010 0.613350 -0.023118 0.041 Uiso 1 1 calc R U . . .
C12 C 0.41911(9) 0.29585(7) 0.34218(11) 0.0237(2) Uani 1 1 d . . . . .
C13 C 0.33431(11) 0.24209(8) 0.27671(14) 0.0342(3) Uani 1 1 d . . . . .
H10 H 0.291900 0.264709 0.198372 0.051 Uiso 1 1 calc R U . . .
H11 H 0.286049 0.229771 0.332975 0.051 Uiso 1 1 calc R U . . .
H12 H 0.369370 0.196538 0.255841 0.051 Uiso 1 1 calc R U . . .
C14 C 0.48614(11) 0.27039(7) 0.46886(13) 0.0326(3) Uani 1 1 d . . . . .
H13 H 0.563122 0.269962 0.466366 0.049 Uiso 1 1 calc R U . . .
H14 H 0.463702 0.220028 0.487086 0.049 Uiso 1 1 calc R U . . .
H15 H 0.475195 0.304610 0.535561 0.049 Uiso 1 1 calc R U . . .
C15 C 0.63550(9) 0.39066(6) 0.34244(11) 0.0197(2) Uani 1 1 d . . . . .
H16 H 0.634463 0.367809 0.262823 0.024 Uiso 1 1 calc R U . . .
C16 C 0.73304(9) 0.39567(6) 0.42259(10) 0.0192(2) Uani 1 1 d . . . . .
C17 C 0.76693(9) 0.42712(6) 0.55799(11) 0.0211(2) Uani 1 1 d . . . . .
C18 C 0.89263(9) 0.42029(7) 0.59040(11) 0.0222(2) Uani 1 1 d . . . . .
C19 C 0.92206(9) 0.37827(6) 0.48538(11) 0.0206(2) Uani 1 1 d . . . . .
C20 C 1.01893(9) 0.34558(6) 0.45733(11) 0.0211(2) Uani 1 1 d . . . . .
C21 C 0.98467(9) 0.31242(7) 0.32377(11) 0.0227(2) Uani 1 1 d . . . . .
C22 C 0.86195(9) 0.32917(6) 0.28388(11) 0.0212(2) Uani 1 1 d . . . . .
C23 C 0.83193(9) 0.36783(6) 0.39208(10) 0.0197(2) Uani 1 1 d . . . . .
C24 C 0.73628(10) 0.50886(7) 0.56885(12) 0.0260(3) Uani 1 1 d . . . . .
H17 H 0.657216 0.513209 0.555478 0.039 Uiso 1 1 calc R U . . .
H18 H 0.761028 0.538231 0.504357 0.039 Uiso 1 1 calc R U . . .
H19 H 0.770938 0.527567 0.653676 0.039 Uiso 1 1 calc R U . . .
C25 C 0.72647(10) 0.37814(7) 0.65464(11) 0.0263(3) Uani 1 1 d . . . . .
H20 H 0.761688 0.393886 0.741134 0.039 Uiso 1 1 calc R U . . .
H21 H 0.744401 0.325870 0.642631 0.039 Uiso 1 1 calc R U . . .
H22 H 0.647568 0.383480 0.641718 0.039 Uiso 1 1 calc R U . . .
C26 C 1.11709(10) 0.34217(7) 0.53473(12) 0.0275(3) Uani 1 1 d . . . . .
H23 H 1.128955 0.362513 0.617986 0.033 Uiso 1 1 calc R U . . .
H24 H 1.175346 0.319388 0.506778 0.033 Uiso 1 1 calc R U . . .
C27 C 1.00022(11) 0.22787(7) 0.32378(14) 0.0339(3) Uani 1 1 d . . . . .
H25 H 1.077694 0.216084 0.351945 0.051 Uiso 1 1 calc R U . . .
H26 H 0.972501 0.208503 0.237612 0.051 Uiso 1 1 calc R U . . .
H27 H 0.960451 0.204827 0.381780 0.051 Uiso 1 1 calc R U . . .
C28 C 1.04244(11) 0.35057(9) 0.23040(12) 0.0339(3) Uani 1 1 d . . . . .
H28 H 1.030898 0.404565 0.232033 0.051 Uiso 1 1 calc R U . . .
H29 H 1.012875 0.331635 0.144323 0.051 Uiso 1 1 calc R U . . .
H30 H 1.120438 0.339863 0.255231 0.051 Uiso 1 1 calc R U . . .
O1 O 0.23994(8) 0.33470(5) 0.02927(9) 0.0333(2) Uani 1 1 d . . . . .
O2 O 0.53961(7) 0.55150(5) 0.32460(8) 0.0273(2) Uani 1 1 d . . . . .
O3 O 0.95272(7) 0.44542(5) 0.68469(8) 0.0314(2) Uani 1 1 d . . . . .
O4 O 0.80314(7) 0.31329(5) 0.18207(8) 0.0293(2) 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
C1 O1 1.2082(15) . ?
C1 C8 1.4990(15) . ?
C1 C2 1.5424(17) . ?
C2 C3 1.5211(16) . ?
C2 C9 1.5281(16) . ?
C2 C10 1.5394(17) . ?
C3 C11 1.3271(18) . ?
C3 C4 1.4488(16) . ?
C4 C8 1.3571(16) . ?
C4 C5 1.4701(15) . ?
C5 O2 1.2107(14) . ?
C5 C6 1.5471(15) . ?
C6 C15 1.5102(15) . ?
C6 C7 1.5354(15) . ?
C7 C12 1.3494(17) . ?
C7 C8 1.4625(16) . ?
C12 C13 1.4940(17) . ?
C12 C14 1.5061(17) . ?
C15 C16 1.3379(16) . ?
C16 C23 1.4526(15) . ?
C16 C17 1.5343(15) . ?
C17 C24 1.5274(16) . ?
C17 C25 1.5386(17) . ?
C17 C18 1.5522(15) . ?
C18 O3 1.2097(14) . ?
C18 C19 1.4786(16) . ?
C19 C23 1.3505(16) . ?
C19 C20 1.4512(16) . ?
C20 C26 1.3298(17) . ?
C20 C21 1.5286(16) . ?
C21 C27 1.5288(17) . ?
C21 C28 1.5349(17) . ?
C21 C22 1.5421(15) . ?
C22 O4 1.2121(14) . ?
C22 C23 1.4811(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
O1 C1 C8 128.61(11) . . ?
O1 C1 C2 123.78(10) . . ?
C8 C1 C2 107.60(9) . . ?
C3 C2 C9 113.31(10) . . ?
C3 C2 C10 111.45(10) . . ?
C9 C2 C10 110.05(10) . . ?
C3 C2 C1 103.78(9) . . ?
C9 C2 C1 109.88(10) . . ?
C10 C2 C1 108.07(10) . . ?
C11 C3 C4 125.95(11) . . ?
C11 C3 C2 127.75(11) . . ?
C4 C3 C2 106.28(10) . . ?
C8 C4 C3 114.75(10) . . ?
C8 C4 C5 110.60(10) . . ?
C3 C4 C5 134.48(11) . . ?
O2 C5 C4 127.84(11) . . ?
O2 C5 C6 126.23(10) . . ?
C4 C5 C6 105.92(9) . . ?
C15 C6 C7 110.42(9) . . ?
C15 C6 C5 108.16(9) . . ?
C7 C6 C5 104.28(9) . . ?
C12 C7 C8 131.09(11) . . ?
C12 C7 C6 123.31(10) . . ?
C8 C7 C6 105.56(9) . . ?
C4 C8 C7 112.48(10) . . ?
C4 C8 C1 107.21(10) . . ?
C7 C8 C1 140.29(10) . . ?
C7 C12 C13 124.21(11) . . ?
C7 C12 C14 120.44(11) . . ?
C13 C12 C14 115.34(11) . . ?
C16 C15 C6 128.51(10) . . ?
C15 C16 C23 122.96(10) . . ?
C15 C16 C17 131.03(10) . . ?
C23 C16 C17 105.99(9) . . ?
C24 C17 C16 113.93(10) . . ?
C24 C17 C25 111.47(10) . . ?
C16 C17 C25 111.91(9) . . ?
C24 C17 C18 108.85(9) . . ?
C16 C17 C18 103.55(9) . . ?
C25 C17 C18 106.51(9) . . ?
O3 C18 C19 128.01(11) . . ?
O3 C18 C17 125.03(11) . . ?
C19 C18 C17 106.95(9) . . ?
C23 C19 C20 113.37(10) . . ?
C23 C19 C18 109.00(10) . . ?
C20 C19 C18 137.62(10) . . ?
C26 C20 C19 126.75(11) . . ?
C26 C20 C21 126.70(11) . . ?
C19 C20 C21 106.48(9) . . ?
C20 C21 C27 112.15(10) . . ?
C20 C21 C28 111.84(10) . . ?
C27 C21 C28 111.19(11) . . ?
C20 C21 C22 103.75(9) . . ?
C27 C21 C22 108.33(10) . . ?
C28 C21 C22 109.23(10) . . ?
O4 C22 C23 127.67(11) . . ?
O4 C22 C21 125.24(10) . . ?
C23 C22 C21 107.09(9) . . ?
C19 C23 C16 113.97(10) . . ?
C19 C23 C22 109.20(10) . . ?
C16 C23 C22 136.82(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -172.69(11) . . . . ?
C8 C1 C2 C3 6.21(12) . . . . ?
O1 C1 C2 C9 -51.23(16) . . . . ?
C8 C1 C2 C9 127.68(11) . . . . ?
O1 C1 C2 C10 68.87(15) . . . . ?
C8 C1 C2 C10 -112.22(10) . . . . ?
C9 C2 C3 C11 57.57(18) . . . . ?
C10 C2 C3 C11 -67.21(17) . . . . ?
C1 C2 C3 C11 176.71(13) . . . . ?
C9 C2 C3 C4 -124.00(11) . . . . ?
C10 C2 C3 C4 111.21(11) . . . . ?
C1 C2 C3 C4 -4.86(12) . . . . ?
C11 C3 C4 C8 -179.73(13) . . . . ?
C2 C3 C4 C8 1.81(13) . . . . ?
C11 C3 C4 C5 5.5(2) . . . . ?
C2 C3 C4 C5 -172.91(12) . . . . ?
C8 C4 C5 O2 -171.69(11) . . . . ?
C3 C4 C5 O2 3.2(2) . . . . ?
C8 C4 C5 C6 6.95(12) . . . . ?
C3 C4 C5 C6 -178.17(12) . . . . ?
O2 C5 C6 C15 -74.18(14) . . . . ?
C4 C5 C6 C15 107.16(10) . . . . ?
O2 C5 C6 C7 168.29(11) . . . . ?
C4 C5 C6 C7 -10.37(11) . . . . ?
C15 C6 C7 C12 76.24(13) . . . . ?
C5 C6 C7 C12 -167.80(11) . . . . ?
C15 C6 C7 C8 -105.81(10) . . . . ?
C5 C6 C7 C8 10.15(11) . . . . ?
C3 C4 C8 C7 -176.26(9) . . . . ?
C5 C4 C8 C7 -0.28(13) . . . . ?
C3 C4 C8 C1 2.26(13) . . . . ?
C5 C4 C8 C1 178.24(9) . . . . ?
C12 C7 C8 C4 171.18(12) . . . . ?
C6 C7 C8 C4 -6.55(12) . . . . ?
C12 C7 C8 C1 -6.6(2) . . . . ?
C6 C7 C8 C1 175.66(13) . . . . ?
O1 C1 C8 C4 173.48(12) . . . . ?
C2 C1 C8 C4 -5.36(12) . . . . ?
O1 C1 C8 C7 -8.7(2) . . . . ?
C2 C1 C8 C7 172.50(13) . . . . ?
C8 C7 C12 C13 5.1(2) . . . . ?
C6 C7 C12 C13 -177.56(11) . . . . ?
C8 C7 C12 C14 -174.00(12) . . . . ?
C6 C7 C12 C14 3.38(17) . . . . ?
C7 C6 C15 C16 -145.63(12) . . . . ?
C5 C6 C15 C16 100.86(13) . . . . ?
C6 C15 C16 C23 179.58(11) . . . . ?
C6 C15 C16 C17 1.1(2) . . . . ?
C15 C16 C17 C24 -58.07(17) . . . . ?
C23 C16 C17 C24 123.28(10) . . . . ?
C15 C16 C17 C25 69.54(16) . . . . ?
C23 C16 C17 C25 -109.12(10) . . . . ?
C15 C16 C17 C18 -176.13(12) . . . . ?
C23 C16 C17 C18 5.21(11) . . . . ?
C24 C17 C18 O3 51.15(16) . . . . ?
C16 C17 C18 O3 172.69(12) . . . . ?
C25 C17 C18 O3 -69.15(15) . . . . ?
C24 C17 C18 C19 -128.74(10) . . . . ?
C16 C17 C18 C19 -7.20(12) . . . . ?
C25 C17 C18 C19 110.95(10) . . . . ?
O3 C18 C19 C23 -173.11(12) . . . . ?
C17 C18 C19 C23 6.78(13) . . . . ?
O3 C18 C19 C20 7.7(2) . . . . ?
C17 C18 C19 C20 -172.41(13) . . . . ?
C23 C19 C20 C26 -174.64(12) . . . . ?
C18 C19 C20 C26 4.5(2) . . . . ?
C23 C19 C20 C21 2.63(13) . . . . ?
C18 C19 C20 C21 -178.21(13) . . . . ?
C26 C20 C21 C27 59.89(16) . . . . ?
C19 C20 C21 C27 -117.38(11) . . . . ?
C26 C20 C21 C28 -65.82(16) . . . . ?
C19 C20 C21 C28 116.91(11) . . . . ?
C26 C20 C21 C22 176.58(12) . . . . ?
C19 C20 C21 C22 -0.69(12) . . . . ?
C20 C21 C22 O4 178.51(11) . . . . ?
C27 C21 C22 O4 -62.15(16) . . . . ?
C28 C21 C22 O4 59.11(16) . . . . ?
C20 C21 C22 C23 -1.20(12) . . . . ?
C27 C21 C22 C23 118.14(11) . . . . ?
C28 C21 C22 C23 -120.61(11) . . . . ?
C20 C19 C23 C16 175.90(9) . . . . ?
C18 C19 C23 C16 -3.50(14) . . . . ?
C20 C19 C23 C22 -3.48(14) . . . . ?
C18 C19 C23 C22 177.12(9) . . . . ?
C15 C16 C23 C19 179.89(11) . . . . ?
C17 C16 C23 C19 -1.32(13) . . . . ?
C15 C16 C23 C22 -1.0(2) . . . . ?
C17 C16 C23 C22 177.82(13) . . . . ?
O4 C22 C23 C19 -176.86(12) . . . . ?
C21 C22 C23 C19 2.84(13) . . . . ?
O4 C22 C23 C16 4.0(2) . . . . ?
C21 C22 C23 C16 -176.33(12) . . . . ?

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.040

