# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_TMBA
_database_code_depnum_ccdc_archive 'CCDC 1872162'
loop_
_audit_author_name
_audit_author_address
'Yasukazu HIRAO'
;Osaka University
Japan
;
_audit_update_record             
;
2018-10-09 deposited with the CCDC.	2019-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6


_chemical_name_systematic        
;
3,3',6,6'-tetramethoxy-10H,10'H-[9,9'-bianthracenylidene]-10,10'-dione
;
_chemical_name_common            3,3',6,6'-tetramethoxybianthrone
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H24 O6'
_chemical_formula_weight         504.51

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.5969(5)
_cell_length_b                   13.4458(6)
_cell_length_c                   15.9778(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.103(8)
_cell_angle_gamma                90
_cell_volume                     2381.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9036
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.46

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8348
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
Empirical Absorption Correction   March 2001 T. Higashi
    Rigaku Corporation, Tokyo, Japan
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus rotating anode'
_diffrn_measurement_device_type  
;
Rigaku MicroMax-007HF,VariMax-Mo and RAPID II
;
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11314
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.381
_diffrn_reflns_theta_max         27.458
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2727
_reflns_number_gt                2179
_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       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    Sir2014
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009)
;
_computing_publication_material  
;
Yadokari-XG 2009 (K. Wakita, T. 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)+(0.0570P)²+1.3489P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2727
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.1003
_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 0.29058(12) 0.47849(9) 0.10280(8) 0.0235(3) Uani 1 1 d . . . . .
C2 C 0.30219(11) 0.38782(9) 0.15809(8) 0.0228(3) Uani 1 1 d . . . . .
C3 C 0.33982(12) 0.39966(10) 0.24917(9) 0.0245(3) Uani 1 1 d . . . . .
H1 H 0.370518 0.461708 0.274561 0.029 Uiso 1 1 calc R U . . .
C4 C 0.33169(12) 0.31983(10) 0.30161(9) 0.0251(3) Uani 1 1 d . . . . .
C5 C 0.28596(12) 0.22872(10) 0.26332(9) 0.0265(3) Uani 1 1 d . . . . .
H2 H 0.275734 0.175147 0.299246 0.032 Uiso 1 1 calc R U . . .
C6 C 0.25579(12) 0.21647(10) 0.17390(9) 0.0250(3) Uani 1 1 d . . . . .
H3 H 0.228099 0.153494 0.149071 0.030 Uiso 1 1 calc R U . . .
C7 C 0.26523(11) 0.29527(9) 0.11892(8) 0.0226(3) Uani 1 1 d . . . . .
C8 C 0.23264(11) 0.28823(9) 0.02168(8) 0.0222(3) Uani 1 1 d . . . . .
C9 C 0.16496(12) 0.37729(9) -0.02214(8) 0.0224(3) Uani 1 1 d . . . . .
C10 C 0.06617(12) 0.37355(10) -0.09782(9) 0.0253(3) Uani 1 1 d . . . . .
H4 H 0.037076 0.310942 -0.122779 0.030 Uiso 1 1 calc R U . . .
C11 C 0.01052(12) 0.45972(10) -0.13661(9) 0.0274(3) Uani 1 1 d . . . . .
H5 H -0.057430 0.455549 -0.187176 0.033 Uiso 1 1 calc R U . . .
C12 C 0.05295(12) 0.55312(10) -0.10238(9) 0.0260(3) Uani 1 1 d . . . . .
C13 C 0.14674(12) 0.55865(9) -0.02521(9) 0.0245(3) Uani 1 1 d . . . . .
H6 H 0.174513 0.621463 -0.000038 0.029 Uiso 1 1 calc R U . . .
C14 C 0.20007(11) 0.47118(9) 0.01525(8) 0.0227(3) Uani 1 1 d . . . . .
O1 O 0.34355(9) 0.55613(7) 0.13051(6) 0.0307(2) Uani 1 1 d . . . . .
O2 O 0.36307(9) 0.32264(7) 0.39111(6) 0.0318(2) Uani 1 1 d . . . . .
C15 C 0.41741(14) 0.41220(11) 0.43183(9) 0.0339(3) Uani 1 1 d . . . . .
H7 H 0.491957 0.424576 0.416459 0.051 Uiso 1 1 calc R U . . .
H8 H 0.436082 0.405823 0.495529 0.051 Uiso 1 1 calc R U . . .
H9 H 0.361556 0.467820 0.411524 0.051 Uiso 1 1 calc R U . . .
O3 O -0.00507(9) 0.63273(7) -0.14803(7) 0.0329(3) Uani 1 1 d . . . . .
C16 C 0.04375(14) 0.72847(11) -0.11934(11) 0.0373(4) Uani 1 1 d . . . . .
H10 H 0.033139 0.742996 -0.061952 0.056 Uiso 1 1 calc R U . . .
H11 H 0.001737 0.778927 -0.161624 0.056 Uiso 1 1 calc R U . . .
H12 H 0.129893 0.729262 -0.114739 0.056 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
C1 O1 1.2261(15) . ?
C1 C14 1.4848(18) . ?
C1 C2 1.4882(17) . ?
C2 C3 1.3999(18) . ?
C2 C7 1.4021(17) . ?
C3 C4 1.3819(18) . ?
C3 H1 0.9500 . ?
C4 O2 1.3684(16) . ?
C4 C5 1.4019(18) . ?
C5 C6 1.3773(19) . ?
C5 H2 0.9500 . ?
C6 C7 1.4011(18) . ?
C6 H3 0.9500 . ?
C7 C8 1.4900(17) . ?
C8 C8 1.365(2) 7 ?
C8 C9 1.4889(17) . ?
C9 C10 1.4008(18) . ?
C9 C14 1.4048(17) . ?
C10 C11 1.3811(18) . ?
C10 H4 0.9500 . ?
C11 C12 1.4000(19) . ?
C11 H5 0.9500 . ?
C12 O3 1.3572(16) . ?
C12 C13 1.3857(19) . ?
C13 C14 1.3959(17) . ?
C13 H6 0.9500 . ?
O2 C15 1.4246(17) . ?
C15 H7 0.9800 . ?
C15 H8 0.9800 . ?
C15 H9 0.9800 . ?
O3 C16 1.4267(17) . ?
C16 H10 0.9800 . ?
C16 H11 0.9800 . ?
C16 H12 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C14 122.47(12) . . ?
O1 C1 C2 122.34(12) . . ?
C14 C1 C2 114.87(11) . . ?
C3 C2 C7 121.72(12) . . ?
C3 C2 C1 118.03(11) . . ?
C7 C2 C1 119.98(11) . . ?
C4 C3 C2 119.08(12) . . ?
C4 C3 H1 120.5 . . ?
C2 C3 H1 120.5 . . ?
O2 C4 C3 124.59(12) . . ?
O2 C4 C5 115.49(11) . . ?
C3 C4 C5 119.91(12) . . ?
C6 C5 C4 120.35(12) . . ?
C6 C5 H2 119.8 . . ?
C4 C5 H2 119.8 . . ?
C5 C6 C7 121.14(12) . . ?
C5 C6 H3 119.4 . . ?
C7 C6 H3 119.4 . . ?
C6 C7 C2 117.47(12) . . ?
C6 C7 C8 124.27(11) . . ?
C2 C7 C8 118.18(11) . . ?
C8 C8 C9 124.08(15) 7 . ?
C8 C8 C7 123.70(15) 7 . ?
C9 C8 C7 112.10(10) . . ?
C10 C9 C14 117.42(12) . . ?
C10 C9 C8 124.15(11) . . ?
C14 C9 C8 118.42(11) . . ?
C11 C10 C9 120.86(12) . . ?
C11 C10 H4 119.6 . . ?
C9 C10 H4 119.6 . . ?
C10 C11 C12 120.86(12) . . ?
C10 C11 H5 119.6 . . ?
C12 C11 H5 119.6 . . ?
O3 C12 C13 124.84(12) . . ?
O3 C12 C11 115.84(12) . . ?
C13 C12 C11 119.31(12) . . ?
C12 C13 C14 119.46(12) . . ?
C12 C13 H6 120.3 . . ?
C14 C13 H6 120.3 . . ?
C13 C14 C9 121.78(12) . . ?
C13 C14 C1 118.34(11) . . ?
C9 C14 C1 119.76(11) . . ?
C4 O2 C15 116.53(10) . . ?
O2 C15 H7 109.5 . . ?
O2 C15 H8 109.5 . . ?
H7 C15 H8 109.5 . . ?
O2 C15 H9 109.5 . . ?
H7 C15 H9 109.5 . . ?
H8 C15 H9 109.5 . . ?
C12 O3 C16 116.86(11) . . ?
O3 C16 H10 109.5 . . ?
O3 C16 H11 109.5 . . ?
H10 C16 H11 109.5 . . ?
O3 C16 H12 109.5 . . ?
H10 C16 H12 109.5 . . ?
H11 C16 H12 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 21.59(18) . . . . ?
C14 C1 C2 C3 -152.00(12) . . . . ?
O1 C1 C2 C7 -164.26(12) . . . . ?
C14 C1 C2 C7 22.15(17) . . . . ?
C7 C2 C3 C4 -4.98(19) . . . . ?
C1 C2 C3 C4 169.06(12) . . . . ?
C2 C3 C4 O2 -178.55(12) . . . . ?
C2 C3 C4 C5 -0.15(19) . . . . ?
O2 C4 C5 C6 -177.56(12) . . . . ?
C3 C4 C5 C6 3.9(2) . . . . ?
C4 C5 C6 C7 -2.6(2) . . . . ?
C5 C6 C7 C2 -2.32(19) . . . . ?
C5 C6 C7 C8 -179.05(12) . . . . ?
C3 C2 C7 C6 6.16(19) . . . . ?
C1 C2 C7 C6 -167.76(12) . . . . ?
C3 C2 C7 C8 -176.90(12) . . . . ?
C1 C2 C7 C8 9.17(18) . . . . ?
C6 C7 C8 C8 -46.3(2) . . . 7 ?
C2 C7 C8 C8 136.94(16) . . . 7 ?
C6 C7 C8 C9 137.40(12) . . . . ?
C2 C7 C8 C9 -39.31(16) . . . . ?
C8 C8 C9 C10 44.2(2) 7 . . . ?
C7 C8 C9 C10 -139.54(13) . . . . ?
C8 C8 C9 C14 -137.16(16) 7 . . . ?
C7 C8 C9 C14 39.07(15) . . . . ?
C14 C9 C10 C11 3.72(19) . . . . ?
C8 C9 C10 C11 -177.65(12) . . . . ?
C9 C10 C11 C12 1.3(2) . . . . ?
C10 C11 C12 O3 177.08(12) . . . . ?
C10 C11 C12 C13 -4.5(2) . . . . ?
O3 C12 C13 C14 -179.36(12) . . . . ?
C11 C12 C13 C14 2.32(19) . . . . ?
C12 C13 C14 C9 2.90(19) . . . . ?
C12 C13 C14 C1 -173.14(12) . . . . ?
C10 C9 C14 C13 -5.88(18) . . . . ?
C8 C9 C14 C13 175.41(11) . . . . ?
C10 C9 C14 C1 170.10(11) . . . . ?
C8 C9 C14 C1 -8.60(18) . . . . ?
O1 C1 C14 C13 -19.88(19) . . . . ?
C2 C1 C14 C13 153.71(11) . . . . ?
O1 C1 C14 C9 164.00(12) . . . . ?
C2 C1 C14 C9 -22.42(17) . . . . ?
C3 C4 O2 C15 -5.68(19) . . . . ?
C5 C4 O2 C15 175.85(12) . . . . ?
C13 C12 O3 C16 7.50(19) . . . . ?
C11 C12 O3 C16 -174.13(12) . . . . ?

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_DMA-Dimer
_database_code_depnum_ccdc_archive 'CCDC 1877284'
loop_
_audit_author_name
_audit_author_address
'Yasukazu HIRAO'
;Osaka University
Japan
;
_audit_update_record             
;
2018-11-06 deposited with the CCDC.	2019-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6

_chemical_name_systematic        
;
3,3',6,6'-tetramethoxy-[9,9'-bianthracene]-10,10'(9H,9'H)-dione
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H26 O6'
_chemical_formula_weight         506.53

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.4848(18)
_cell_length_b                   7.8190(6)
_cell_length_c                   13.9952(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.559(7)
_cell_angle_gamma                90
_cell_volume                     2786.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9513
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      27.46

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7563
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
Empirical Absorption Correction   March 2001 T. Higashi
    Rigaku Corporation, Tokyo, Japan
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus rotating anode'
_diffrn_measurement_device_type  
;
Rigaku MicroMax-007HF,VariMax-Mo and RAPID II
;
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13021
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.725
_diffrn_reflns_theta_max         27.456
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3190
_reflns_number_gt                2516
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    Sir2014
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009)
;
_computing_publication_material  
;
Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009)
;
_refine_special_details          
;The included THF solvent molecule are disordered.
Attempts to model disordered solvent molecules were unsuccessful. 
We therefore employed PLATON/SQUEEZE to make the solvent-free 
diffraction intensities.,SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3190
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1950
_refine_ls_wR_factor_gt          0.1725
_refine_ls_goodness_of_fit_ref   0.808
_refine_ls_restrained_S_all      0.808
_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 0.08214(6) 0.43456(19) 0.14526(11) 0.0384(3) Uani 1 1 d . . . . .
C2 C 0.02476(5) 0.40932(18) 0.12962(9) 0.0336(3) Uani 1 1 d . . . . .
C3 C 0.00677(6) 0.25200(19) 0.09472(11) 0.0385(3) Uani 1 1 d . . . . .
H1 H 0.031095 0.163077 0.083257 0.046 Uiso 1 1 calc R U . . .
C4 C -0.04638(6) 0.22487(19) 0.07672(10) 0.0386(3) Uani 1 1 d . . . . .
C5 C -0.08159(6) 0.3583(2) 0.08798(10) 0.0395(3) Uani 1 1 d . . . . .
H2 H -0.117943 0.342021 0.072694 0.047 Uiso 1 1 calc R U . . .
C6 C -0.06343(6) 0.51523(19) 0.12164(10) 0.0365(3) Uani 1 1 d . . . . .
H3 H -0.087706 0.606232 0.128150 0.044 Uiso 1 1 calc R U . . .
C7 C -0.01053(5) 0.54308(17) 0.14615(9) 0.0315(3) Uani 1 1 d . . . . .
C8 C 0.00757(5) 0.70566(17) 0.19467(9) 0.0308(3) Uani 1 1 d . . . . .
H4 H -0.011474 0.802857 0.162196 0.037 Uiso 1 1 calc R U . . .
C9 C 0.06546(5) 0.73853(18) 0.18915(9) 0.0319(3) Uani 1 1 d . . . . .
C10 C 0.08525(6) 0.90231(19) 0.21068(10) 0.0364(3) Uani 1 1 d . . . . .
H5 H 0.061628 0.991508 0.225404 0.044 Uiso 1 1 calc R U . . .
C11 C 0.13807(6) 0.9358(2) 0.21083(12) 0.0412(4) Uani 1 1 d . . . . .
H6 H 0.150633 1.048130 0.223967 0.049 Uiso 1 1 calc R U . . .
C12 C 0.17345(6) 0.8050(2) 0.19171(12) 0.0430(4) Uani 1 1 d . . . . .
C13 C 0.15521(6) 0.6422(2) 0.17045(12) 0.0410(4) Uani 1 1 d . . . . .
H7 H 0.179140 0.553066 0.157223 0.049 Uiso 1 1 calc R U . . .
C14 C 0.10107(5) 0.61010(18) 0.16862(10) 0.0345(3) Uani 1 1 d . . . . .
O1 O 0.11334(5) 0.31693(15) 0.13643(10) 0.0576(4) Uani 1 1 d . . . . .
O2 O -0.06036(5) 0.06322(14) 0.04707(9) 0.0506(3) Uani 1 1 d . . . . .
C15 C -0.11449(7) 0.0252(2) 0.03440(13) 0.0509(4) Uani 1 1 d . . . . .
H8 H -0.131721 0.043447 0.094776 0.076 Uiso 1 1 calc R U . . .
H9 H -0.118833 -0.094422 0.014627 0.076 Uiso 1 1 calc R U . . .
H10 H -0.130410 0.100100 -0.014973 0.076 Uiso 1 1 calc R U . . .
O3 O 0.22516(5) 0.85393(18) 0.19453(11) 0.0639(4) Uani 1 1 d . . . . .
C16 C 0.26274(7) 0.7295(3) 0.1702(2) 0.0859(9) Uani 1 1 d . . . . .
H11 H 0.260136 0.630304 0.212492 0.129 Uiso 1 1 calc R U . . .
H12 H 0.298070 0.778640 0.177556 0.129 Uiso 1 1 calc R U . . .
H13 H 0.256005 0.693631 0.103678 0.129 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
C1 O1 1.2256(19) . ?
C1 C2 1.482(2) . ?
C1 C14 1.486(2) . ?
C2 C3 1.394(2) . ?
C2 C7 1.405(2) . ?
C3 C4 1.383(2) . ?
C3 H1 0.9500 . ?
C4 O2 1.3724(18) . ?
C4 C5 1.389(2) . ?
C5 C6 1.387(2) . ?
C5 H2 0.9500 . ?
C6 C7 1.3932(19) . ?
C6 H3 0.9500 . ?
C7 C8 1.5039(19) . ?
C8 C9 1.5029(18) . ?
C8 C8 1.613(3) 2 ?
C8 H4 1.0000 . ?
C9 C14 1.392(2) . ?
C9 C10 1.404(2) . ?
C10 C11 1.371(2) . ?
C10 H5 0.9500 . ?
C11 C12 1.397(2) . ?
C11 H6 0.9500 . ?
C12 O3 1.3712(19) . ?
C12 C13 1.383(2) . ?
C13 C14 1.401(2) . ?
C13 H7 0.9500 . ?
O2 C15 1.415(2) . ?
C15 H8 0.9800 . ?
C15 H9 0.9800 . ?
C15 H10 0.9800 . ?
O3 C16 1.417(3) . ?
C16 H11 0.9800 . ?
C16 H12 0.9800 . ?
C16 H13 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 121.69(14) . . ?
O1 C1 C14 120.63(13) . . ?
C2 C1 C14 117.64(12) . . ?
C3 C2 C7 120.77(13) . . ?
C3 C2 C1 118.45(13) . . ?
C7 C2 C1 120.74(12) . . ?
C4 C3 C2 120.24(14) . . ?
C4 C3 H1 119.9 . . ?
C2 C3 H1 119.9 . . ?
O2 C4 C3 115.80(13) . . ?
O2 C4 C5 124.43(14) . . ?
C3 C4 C5 119.76(13) . . ?
C6 C5 C4 119.70(13) . . ?
C6 C5 H2 120.2 . . ?
C4 C5 H2 120.2 . . ?
C5 C6 C7 121.78(13) . . ?
C5 C6 H3 119.1 . . ?
C7 C6 H3 119.1 . . ?
C6 C7 C2 117.55(12) . . ?
C6 C7 C8 121.15(12) . . ?
C2 C7 C8 121.18(12) . . ?
C9 C8 C7 113.79(11) . . ?
C9 C8 C8 109.08(12) . 2 ?
C7 C8 C8 110.60(9) . 2 ?
C9 C8 H4 107.7 . . ?
C7 C8 H4 107.7 . . ?
C8 C8 H4 107.7 2 . ?
C14 C9 C10 118.09(13) . . ?
C14 C9 C8 122.53(12) . . ?
C10 C9 C8 119.27(12) . . ?
C11 C10 C9 121.18(14) . . ?
C11 C10 H5 119.4 . . ?
C9 C10 H5 119.4 . . ?
C10 C11 C12 120.11(14) . . ?
C10 C11 H6 119.9 . . ?
C12 C11 H6 119.9 . . ?
O3 C12 C13 125.21(15) . . ?
O3 C12 C11 114.69(14) . . ?
C13 C12 C11 120.09(14) . . ?
C12 C13 C14 119.35(14) . . ?
C12 C13 H7 120.3 . . ?
C14 C13 H7 120.3 . . ?
C9 C14 C13 121.15(13) . . ?
C9 C14 C1 120.21(12) . . ?
C13 C14 C1 118.64(13) . . ?
C4 O2 C15 118.04(13) . . ?
O2 C15 H8 109.5 . . ?
O2 C15 H9 109.5 . . ?
H8 C15 H9 109.5 . . ?
O2 C15 H10 109.5 . . ?
H8 C15 H10 109.5 . . ?
H9 C15 H10 109.5 . . ?
C12 O3 C16 117.42(15) . . ?
O3 C16 H11 109.5 . . ?
O3 C16 H12 109.5 . . ?
H11 C16 H12 109.5 . . ?
O3 C16 H13 109.5 . . ?
H11 C16 H13 109.5 . . ?
H12 C16 H13 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -6.6(2) . . . . ?
C14 C1 C2 C3 171.17(12) . . . . ?
O1 C1 C2 C7 175.83(15) . . . . ?
C14 C1 C2 C7 -6.4(2) . . . . ?
C7 C2 C3 C4 -0.6(2) . . . . ?
C1 C2 C3 C4 -178.26(12) . . . . ?
C2 C3 C4 O2 -176.87(13) . . . . ?
C2 C3 C4 C5 3.9(2) . . . . ?
O2 C4 C5 C6 177.73(13) . . . . ?
C3 C4 C5 C6 -3.1(2) . . . . ?
C4 C5 C6 C7 -1.0(2) . . . . ?
C5 C6 C7 C2 4.1(2) . . . . ?
C5 C6 C7 C8 -171.78(12) . . . . ?
C3 C2 C7 C6 -3.3(2) . . . . ?
C1 C2 C7 C6 174.24(12) . . . . ?
C3 C2 C7 C8 172.60(12) . . . . ?
C1 C2 C7 C8 -9.8(2) . . . . ?
C6 C7 C8 C9 -162.45(12) . . . . ?
C2 C7 C8 C9 21.78(18) . . . . ?
C6 C7 C8 C8 74.37(16) . . . 2 ?
C2 C7 C8 C8 -101.40(16) . . . 2 ?
C7 C8 C9 C14 -18.84(18) . . . . ?
C8 C8 C9 C14 105.17(12) 2 . . . ?
C7 C8 C9 C10 164.88(11) . . . . ?
C8 C8 C9 C10 -71.11(12) 2 . . . ?
C14 C9 C10 C11 0.5(2) . . . . ?
C8 C9 C10 C11 176.96(13) . . . . ?
C9 C10 C11 C12 -1.6(2) . . . . ?
C10 C11 C12 O3 -179.59(14) . . . . ?
C10 C11 C12 C13 1.5(2) . . . . ?
O3 C12 C13 C14 -179.03(15) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
C10 C9 C14 C13 0.8(2) . . . . ?
C8 C9 C14 C13 -175.56(12) . . . . ?
C10 C9 C14 C1 -179.92(12) . . . . ?
C8 C9 C14 C1 3.8(2) . . . . ?
C12 C13 C14 C9 -0.9(2) . . . . ?
C12 C13 C14 C1 179.76(13) . . . . ?
O1 C1 C14 C9 -172.72(14) . . . . ?
C2 C1 C14 C9 9.5(2) . . . . ?
O1 C1 C14 C13 6.6(2) . . . . ?
C2 C1 C14 C13 -171.14(12) . . . . ?
C3 C4 O2 C15 175.48(13) . . . . ?
C5 C4 O2 C15 -5.3(2) . . . . ?
C13 C12 O3 C16 2.5(3) . . . . ?
C11 C12 O3 C16 -176.35(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H6 O1 0.95 2.59 3.2099(19) 123.0 1_565

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.043



