# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_KIK-0017-2
_database_code_depnum_ccdc_archive 'CCDC 2007772'
loop_
_audit_author_name
_audit_author_address
'Takeshi Yasui'
;Nagoya University
Japan
;
_audit_update_record             
;
2020-06-03 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21 H16 O3'
_chemical_formula_moiety         'C21 H16 O3'
_chemical_formula_weight         316.36
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,+Z
7 +X,-1/2-Y,-1/2+Z
8 -1/2+X,+Y,-1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.8744(6)
_cell_length_b                   11.4021(7)
_cell_length_c                   60.208(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     6092.2(7)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    7422
_cell_measurement_theta_min      3.94
_cell_measurement_theta_max      68.00
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2656.00
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.601
_exptl_absorpt_correction_T_max  0.929

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            62519
_diffrn_reflns_av_R_equivalents  0.1638
_diffrn_reflns_theta_max         68.203
_diffrn_reflns_theta_min         4.406
_diffrn_reflns_theta_full        67.687
_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
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -69
_diffrn_reflns_limit_l_max       72
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5578
_reflns_number_gt                2997
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1600
_refine_ls_R_factor_gt           0.1092
_refine_ls_wR_factor_ref         0.3326
_refine_ls_wR_factor_gt          0.2772
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5578
_refine_ls_number_parameters     434
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1606P)²+3.6736P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00063(17)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.6303(4) 0.4049(3) 0.49064(6) 0.0559(10) Uani 1 1 d . . . . .
O2 O 0.6816(4) 0.5866(3) 0.47893(6) 0.0568(10) Uani 1 1 d . . . . .
O3 O 0.7013(4) -0.0287(3) 0.40457(6) 0.0577(10) Uani 1 1 d . . . . .
O4 O 0.4849(4) 0.2838(3) 0.35816(6) 0.0577(11) Uani 1 1 d . . . . .
O5 O 0.4826(5) 0.1271(4) 0.33584(7) 0.0712(13) Uani 1 1 d . . . . .
O6 O 0.2474(5) 0.7953(3) 0.29975(6) 0.0665(12) Uani 1 1 d . . . . .
C1 C 0.5435(7) 0.3033(5) 0.48283(8) 0.0530(14) Uani 1 1 d . . . . .
H1A H 0.4472 0.2987 0.4904 0.064 Uiso 1 1 calc R U . . .
H1B H 0.5985 0.2311 0.4854 0.064 Uiso 1 1 calc R U . . .
C2 C 0.5211(6) 0.3238(5) 0.45826(8) 0.0467(13) Uani 1 1 d . . . . .
C3 C 0.5419(6) 0.4504(5) 0.45532(8) 0.0488(13) Uani 1 1 d . . . . .
C4 C 0.6259(6) 0.4915(6) 0.47541(9) 0.0530(14) Uani 1 1 d . . . . .
C5 C 0.5137(6) 0.2363(5) 0.44303(8) 0.0442(12) Uani 1 1 d . . . . .
C6 C 0.4985(6) 0.1119(5) 0.44960(8) 0.0481(13) Uani 1 1 d . . . . .
C7 C 0.4097(6) 0.0782(5) 0.46791(8) 0.0514(14) Uani 1 1 d . . . . .
H7 H 0.3545 0.1345 0.4756 0.062 Uiso 1 1 calc R U . . .
C8 C 0.4035(7) -0.0381(5) 0.47468(9) 0.0562(15) Uani 1 1 d . . . . .
H8 H 0.3450 -0.0585 0.4869 0.067 Uiso 1 1 calc R U . . .
C9 C 0.4835(7) -0.1246(5) 0.46340(9) 0.0588(16) Uani 1 1 d . . . . .
H9 H 0.4831 -0.2017 0.4684 0.071 Uiso 1 1 calc R U . . .
C10 C 0.5634(6) -0.0935(5) 0.44467(9) 0.0528(14) Uani 1 1 d . . . . .
H10 H 0.6144 -0.1512 0.4367 0.063 Uiso 1 1 calc R U . . .
C11 C 0.5696(6) 0.0220(5) 0.43740(8) 0.0446(12) Uani 1 1 d . . . . .
C12 C 0.6461(6) 0.0491(5) 0.41612(9) 0.0495(13) Uani 1 1 d . . . . .
C13 C 0.6536(6) 0.1747(5) 0.40879(8) 0.0491(13) Uani 1 1 d . . . . .
H13A H 0.6468 0.1769 0.3927 0.059 Uiso 1 1 calc R U . . .
H13B H 0.7514 0.2060 0.4129 0.059 Uiso 1 1 calc R U . . .
C14 C 0.5309(6) 0.2556(5) 0.41844(8) 0.0503(13) Uani 1 1 d . . . . .
H14A H 0.5576 0.3368 0.4157 0.060 Uiso 1 1 calc R U . . .
H14B H 0.4357 0.2400 0.4111 0.060 Uiso 1 1 calc R U . . .
C15 C 0.4978(6) 0.5354(5) 0.44095(8) 0.0489(13) Uani 1 1 d . . . . .
H15 H 0.5408 0.6081 0.4440 0.059 Uiso 1 1 calc R U . . .
C16 C 0.3975(6) 0.5374(5) 0.42179(8) 0.0458(13) Uani 1 1 d . . . . .
C17 C 0.4029(6) 0.6347(5) 0.40766(8) 0.0500(13) Uani 1 1 d . . . . .
H17 H 0.4707 0.6949 0.4107 0.060 Uiso 1 1 calc R U . . .
C18 C 0.3099(6) 0.6434(5) 0.38938(9) 0.0518(14) Uani 1 1 d . . . . .
H18 H 0.3181 0.7070 0.3798 0.062 Uiso 1 1 calc R U . . .
C19 C 0.2035(6) 0.5558(5) 0.38543(9) 0.0512(14) Uani 1 1 d . . . . .
H19 H 0.1391 0.5610 0.3733 0.061 Uiso 1 1 calc R U . . .
C20 C 0.1944(6) 0.4609(5) 0.39974(9) 0.0515(14) Uani 1 1 d . . . . .
H20 H 0.1236 0.4024 0.3971 0.062 Uiso 1 1 calc R U . . .
C21 C 0.2878(6) 0.4520(5) 0.41764(9) 0.0480(13) Uani 1 1 d . . . . .
H21 H 0.2784 0.3885 0.4272 0.058 Uiso 1 1 calc R U . . .
C22 C 0.5325(7) 0.4073(5) 0.35736(9) 0.0529(14) Uani 1 1 d . . . . .
H22A H 0.6248 0.4190 0.3657 0.063 Uiso 1 1 calc R U . . .
H22B H 0.4549 0.4583 0.3633 0.063 Uiso 1 1 calc R U . . .
C23 C 0.5573(6) 0.4305(5) 0.33288(8) 0.0443(12) Uani 1 1 d . . . . .
C24 C 0.5791(6) 0.3157(5) 0.32273(8) 0.0488(13) Uani 1 1 d . . . . .
C25 C 0.5104(7) 0.2288(6) 0.33842(9) 0.0585(15) Uani 1 1 d . . . . .
C26 C 0.5306(6) 0.5344(5) 0.32248(8) 0.0445(12) Uani 1 1 d . . . . .
C27 C 0.5217(6) 0.6463(5) 0.33445(8) 0.0462(13) Uani 1 1 d . . . . .
C28 C 0.6095(6) 0.6679(5) 0.35314(8) 0.0468(13) Uani 1 1 d . . . . .
H28 H 0.6665 0.6076 0.3593 0.056 Uiso 1 1 calc R U . . .
C29 C 0.6132(6) 0.7787(5) 0.36279(9) 0.0512(14) Uani 1 1 d . . . . .
H29 H 0.6744 0.7920 0.3751 0.061 Uiso 1 1 calc R U . . .
C30 C 0.5267(7) 0.8694(5) 0.35432(9) 0.0564(15) Uani 1 1 d . . . . .
H30 H 0.5302 0.9434 0.3608 0.068 Uiso 1 1 calc R U . . .
C31 C 0.4353(6) 0.8490(5) 0.33622(9) 0.0524(14) Uani 1 1 d . . . . .
H31 H 0.3758 0.9094 0.3307 0.063 Uiso 1 1 calc R U . . .
C32 C 0.4310(6) 0.7387(5) 0.32611(8) 0.0481(13) Uani 1 1 d . . . . .
C33 C 0.3351(6) 0.7198(5) 0.30607(9) 0.0510(14) Uani 1 1 d . . . . .
C34 C 0.3503(6) 0.6047(5) 0.29429(9) 0.0528(14) Uani 1 1 d . . . . .
H34A H 0.3369 0.6176 0.2785 0.063 Uiso 1 1 calc R U . . .
H34B H 0.2701 0.5531 0.2992 0.063 Uiso 1 1 calc R U . . .
C35 C 0.5023(6) 0.5427(5) 0.29801(8) 0.0488(13) Uani 1 1 d . . . . .
H35A H 0.4997 0.4648 0.2915 0.059 Uiso 1 1 calc R U . . .
H35B H 0.5825 0.5868 0.2909 0.059 Uiso 1 1 calc R U . . .
C36 C 0.6530(6) 0.2757(5) 0.30471(8) 0.0506(14) Uani 1 1 d . . . . .
H36 H 0.6362 0.1969 0.3016 0.061 Uiso 1 1 calc R U . . .
C37 C 0.7546(6) 0.3341(5) 0.28921(8) 0.0501(13) Uani 1 1 d . . . . .
C38 C 0.7794(7) 0.2849(5) 0.26835(9) 0.0562(15) Uani 1 1 d . . . . .
H38 H 0.7260 0.2180 0.2643 0.067 Uiso 1 1 calc R U . . .
C39 C 0.8805(7) 0.3321(6) 0.25348(9) 0.0623(17) Uani 1 1 d . . . . .
H39 H 0.8920 0.2997 0.2394 0.075 Uiso 1 1 calc R U . . .
C40 C 0.9650(7) 0.4288(6) 0.25982(10) 0.0635(16) Uani 1 1 d . . . . .
H40 H 1.0356 0.4602 0.2501 0.076 Uiso 1 1 calc R U . . .
C41 C 0.9448(7) 0.4787(5) 0.28056(9) 0.0577(15) Uani 1 1 d . . . . .
H41 H 1.0022 0.5433 0.2847 0.069 Uiso 1 1 calc R U . . .
C42 C 0.8402(6) 0.4333(5) 0.29500(9) 0.0516(14) Uani 1 1 d . . . . .
H42 H 0.8259 0.4685 0.3088 0.062 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C4 1.348(6) . ?
O1 C1 1.468(6) . ?
O2 C4 1.211(6) . ?
O3 C12 1.229(6) . ?
O4 C25 1.362(7) . ?
O4 C22 1.471(6) . ?
O5 C25 1.196(7) . ?
O6 C33 1.222(6) . ?
C1 C2 1.511(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C5 1.356(7) . ?
C2 C3 1.467(7) . ?
C3 C15 1.357(7) . ?
C3 C4 1.496(7) . ?
C5 C6 1.479(7) . ?
C5 C14 1.504(7) . ?
C6 C7 1.409(7) . ?
C6 C11 1.410(7) . ?
C7 C8 1.388(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.390(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.482(7) . ?
C12 C13 1.500(7) . ?
C13 C14 1.541(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.457(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.399(7) . ?
C16 C21 1.400(7) . ?
C17 C18 1.379(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.395(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.386(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.363(7) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.514(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C26 1.361(7) . ?
C23 C24 1.457(7) . ?
C24 C36 1.347(7) . ?
C24 C25 1.499(8) . ?
C26 C27 1.467(7) . ?
C26 C35 1.498(7) . ?
C27 C28 1.391(7) . ?
C27 C32 1.418(7) . ?
C28 C29 1.390(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.386(7) . ?
C29 H29 0.9300 . ?
C30 C31 1.378(8) . ?
C30 H30 0.9300 . ?
C31 C32 1.398(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.492(7) . ?
C33 C34 1.498(7) . ?
C34 C35 1.539(7) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.459(7) . ?
C36 H36 0.9300 . ?
C37 C38 1.393(7) . ?
C37 C42 1.406(7) . ?
C38 C39 1.377(8) . ?
C38 H38 0.9300 . ?
C39 C40 1.387(8) . ?
C39 H39 0.9300 . ?
C40 C41 1.384(8) . ?
C40 H40 0.9300 . ?
C41 C42 1.372(8) . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?

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
C4 O1 C1 110.2(4) . . ?
C25 O4 C22 111.3(4) . . ?
O1 C1 C2 105.1(4) . . ?
O1 C1 H1A 110.7 . . ?
C2 C1 H1A 110.7 . . ?
O1 C1 H1B 110.7 . . ?
C2 C1 H1B 110.7 . . ?
H1A C1 H1B 108.8 . . ?
C5 C2 C3 130.4(5) . . ?
C5 C2 C1 123.7(5) . . ?
C3 C2 C1 104.7(4) . . ?
C15 C3 C2 138.1(5) . . ?
C15 C3 C4 115.9(5) . . ?
C2 C3 C4 105.8(5) . . ?
O2 C4 O1 121.7(5) . . ?
O2 C4 C3 128.7(5) . . ?
O1 C4 C3 109.6(5) . . ?
C2 C5 C6 121.9(5) . . ?
C2 C5 C14 123.6(5) . . ?
C6 C5 C14 114.4(4) . . ?
C7 C6 C11 117.4(5) . . ?
C7 C6 C5 121.5(5) . . ?
C11 C6 C5 121.1(5) . . ?
C8 C7 C6 120.8(5) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.9(5) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 118.6(6) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C9 C10 C11 121.4(5) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C6 120.5(5) . . ?
C10 C11 C12 119.2(5) . . ?
C6 C11 C12 120.3(5) . . ?
O3 C12 C11 121.4(5) . . ?
O3 C12 C13 120.3(5) . . ?
C11 C12 C13 118.3(5) . . ?
C12 C13 C14 115.4(4) . . ?
C12 C13 H13A 108.4 . . ?
C14 C13 H13A 108.4 . . ?
C12 C13 H13B 108.4 . . ?
C14 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C5 C14 C13 110.8(4) . . ?
C5 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C3 C15 C16 133.8(5) . . ?
C3 C15 H15 113.1 . . ?
C16 C15 H15 113.1 . . ?
C17 C16 C21 117.8(5) . . ?
C17 C16 C15 118.2(5) . . ?
C21 C16 C15 123.7(5) . . ?
C18 C17 C16 121.5(5) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 119.3(5) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C20 C19 C18 119.5(5) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C21 C20 C19 120.9(5) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C16 120.8(5) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
O4 C22 C23 103.9(4) . . ?
O4 C22 H22A 111.0 . . ?
C23 C22 H22A 111.0 . . ?
O4 C22 H22B 111.0 . . ?
C23 C22 H22B 111.0 . . ?
H22A C22 H22B 109.0 . . ?
C26 C23 C24 127.8(5) . . ?
C26 C23 C22 125.1(5) . . ?
C24 C23 C22 105.7(4) . . ?
C36 C24 C23 134.9(5) . . ?
C36 C24 C25 118.8(5) . . ?
C23 C24 C25 106.0(5) . . ?
O5 C25 O4 121.7(5) . . ?
O5 C25 C24 130.0(6) . . ?
O4 C25 C24 108.3(5) . . ?
C23 C26 C27 122.7(5) . . ?
C23 C26 C35 122.4(5) . . ?
C27 C26 C35 114.8(4) . . ?
C28 C27 C32 118.2(5) . . ?
C28 C27 C26 121.4(5) . . ?
C32 C27 C26 120.2(5) . . ?
C29 C28 C27 120.8(5) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C30 C29 C28 120.8(5) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C31 C30 C29 119.4(5) . . ?
C31 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
C30 C31 C32 120.8(5) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C31 C32 C27 119.9(5) . . ?
C31 C32 C33 119.8(5) . . ?
C27 C32 C33 120.2(5) . . ?
O6 C33 C32 120.9(5) . . ?
O6 C33 C34 121.9(5) . . ?
C32 C33 C34 117.2(5) . . ?
C33 C34 C35 114.4(5) . . ?
C33 C34 H34A 108.7 . . ?
C35 C34 H34A 108.7 . . ?
C33 C34 H34B 108.7 . . ?
C35 C34 H34B 108.7 . . ?
H34A C34 H34B 107.6 . . ?
C26 C35 C34 108.6(4) . . ?
C26 C35 H35A 110.0 . . ?
C34 C35 H35A 110.0 . . ?
C26 C35 H35B 110.0 . . ?
C34 C35 H35B 110.0 . . ?
H35A C35 H35B 108.4 . . ?
C24 C36 C37 131.4(5) . . ?
C24 C36 H36 114.3 . . ?
C37 C36 H36 114.3 . . ?
C38 C37 C42 117.5(5) . . ?
C38 C37 C36 119.4(5) . . ?
C42 C37 C36 122.9(5) . . ?
C39 C38 C37 122.1(6) . . ?
C39 C38 H38 118.9 . . ?
C37 C38 H38 118.9 . . ?
C38 C39 C40 118.9(5) . . ?
C38 C39 H39 120.5 . . ?
C40 C39 H39 120.5 . . ?
C41 C40 C39 120.4(6) . . ?
C41 C40 H40 119.8 . . ?
C39 C40 H40 119.8 . . ?
C42 C41 C40 120.2(6) . . ?
C42 C41 H41 119.9 . . ?
C40 C41 H41 119.9 . . ?
C41 C42 C37 120.8(5) . . ?
C41 C42 H42 119.6 . . ?
C37 C42 H42 119.6 . . ?

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
C4 O1 C1 C2 15.6(6) . . . . ?
O1 C1 C2 C5 147.5(5) . . . . ?
O1 C1 C2 C3 -21.3(5) . . . . ?
C5 C2 C3 C15 37.7(10) . . . . ?
C1 C2 C3 C15 -154.6(7) . . . . ?
C5 C2 C3 C4 -148.4(5) . . . . ?
C1 C2 C3 C4 19.3(5) . . . . ?
C1 O1 C4 O2 175.1(5) . . . . ?
C1 O1 C4 C3 -3.5(6) . . . . ?
C15 C3 C4 O2 -13.5(9) . . . . ?
C2 C3 C4 O2 171.1(5) . . . . ?
C15 C3 C4 O1 165.0(5) . . . . ?
C2 C3 C4 O1 -10.5(6) . . . . ?
C3 C2 C5 C6 177.3(5) . . . . ?
C1 C2 C5 C6 11.6(8) . . . . ?
C3 C2 C5 C14 1.8(9) . . . . ?
C1 C2 C5 C14 -163.9(5) . . . . ?
C2 C5 C6 C7 37.1(7) . . . . ?
C14 C5 C6 C7 -147.0(5) . . . . ?
C2 C5 C6 C11 -144.5(5) . . . . ?
C14 C5 C6 C11 31.4(7) . . . . ?
C11 C6 C7 C8 5.3(8) . . . . ?
C5 C6 C7 C8 -176.2(5) . . . . ?
C6 C7 C8 C9 -0.7(9) . . . . ?
C7 C8 C9 C10 -3.2(9) . . . . ?
C8 C9 C10 C11 2.3(9) . . . . ?
C9 C10 C11 C6 2.5(8) . . . . ?
C9 C10 C11 C12 -174.8(5) . . . . ?
C7 C6 C11 C10 -6.2(7) . . . . ?
C5 C6 C11 C10 175.3(5) . . . . ?
C7 C6 C11 C12 171.1(5) . . . . ?
C5 C6 C11 C12 -7.4(7) . . . . ?
C10 C11 C12 O3 1.6(8) . . . . ?
C6 C11 C12 O3 -175.7(5) . . . . ?
C10 C11 C12 C13 -179.0(5) . . . . ?
C6 C11 C12 C13 3.7(7) . . . . ?
O3 C12 C13 C14 155.7(5) . . . . ?
C11 C12 C13 C14 -23.8(7) . . . . ?
C2 C5 C14 C13 126.6(5) . . . . ?
C6 C5 C14 C13 -49.3(6) . . . . ?
C12 C13 C14 C5 46.0(6) . . . . ?
C2 C3 C15 C16 4.3(11) . . . . ?
C4 C3 C15 C16 -169.1(5) . . . . ?
C3 C15 C16 C17 -166.0(6) . . . . ?
C3 C15 C16 C21 19.3(9) . . . . ?
C21 C16 C17 C18 -4.0(8) . . . . ?
C15 C16 C17 C18 -179.1(5) . . . . ?
C16 C17 C18 C19 2.9(8) . . . . ?
C17 C18 C19 C20 -0.9(8) . . . . ?
C18 C19 C20 C21 0.1(8) . . . . ?
C19 C20 C21 C16 -1.3(8) . . . . ?
C17 C16 C21 C20 3.2(8) . . . . ?
C15 C16 C21 C20 178.0(5) . . . . ?
C25 O4 C22 C23 12.9(6) . . . . ?
O4 C22 C23 C26 146.2(5) . . . . ?
O4 C22 C23 C24 -20.8(5) . . . . ?
C26 C23 C24 C36 40.9(10) . . . . ?
C22 C23 C24 C36 -152.5(6) . . . . ?
C26 C23 C24 C25 -145.4(5) . . . . ?
C22 C23 C24 C25 21.1(5) . . . . ?
C22 O4 C25 O5 178.2(6) . . . . ?
C22 O4 C25 C24 0.0(6) . . . . ?
C36 C24 C25 O5 -16.7(10) . . . . ?
C23 C24 C25 O5 168.4(6) . . . . ?
C36 C24 C25 O4 161.2(5) . . . . ?
C23 C24 C25 O4 -13.6(6) . . . . ?
C24 C23 C26 C27 -175.3(5) . . . . ?
C22 C23 C26 C27 20.6(8) . . . . ?
C24 C23 C26 C35 7.0(8) . . . . ?
C22 C23 C26 C35 -157.1(5) . . . . ?
C23 C26 C27 C28 33.7(7) . . . . ?
C35 C26 C27 C28 -148.4(5) . . . . ?
C23 C26 C27 C32 -151.2(5) . . . . ?
C35 C26 C27 C32 26.7(7) . . . . ?
C32 C27 C28 C29 -2.7(7) . . . . ?
C26 C27 C28 C29 172.4(5) . . . . ?
C27 C28 C29 C30 1.5(8) . . . . ?
C28 C29 C30 C31 0.5(8) . . . . ?
C29 C30 C31 C32 -1.1(8) . . . . ?
C30 C31 C32 C27 -0.2(8) . . . . ?
C30 C31 C32 C33 -178.0(5) . . . . ?
C28 C27 C32 C31 2.1(8) . . . . ?
C26 C27 C32 C31 -173.2(4) . . . . ?
C28 C27 C32 C33 179.9(5) . . . . ?
C26 C27 C32 C33 4.6(7) . . . . ?
C31 C32 C33 O6 -8.1(8) . . . . ?
C27 C32 C33 O6 174.1(5) . . . . ?
C31 C32 C33 C34 172.3(5) . . . . ?
C27 C32 C33 C34 -5.5(7) . . . . ?
O6 C33 C34 C35 156.5(5) . . . . ?
C32 C33 C34 C35 -23.9(7) . . . . ?
C23 C26 C35 C34 124.1(5) . . . . ?
C27 C26 C35 C34 -53.7(6) . . . . ?
C33 C34 C35 C26 52.4(6) . . . . ?
C23 C24 C36 C37 6.9(11) . . . . ?
C25 C24 C36 C37 -166.1(5) . . . . ?
C24 C36 C37 C38 -160.2(6) . . . . ?
C24 C36 C37 C42 25.6(9) . . . . ?
C42 C37 C38 C39 -1.7(8) . . . . ?
C36 C37 C38 C39 -176.2(5) . . . . ?
C37 C38 C39 C40 2.8(9) . . . . ?
C38 C39 C40 C41 -1.7(9) . . . . ?
C39 C40 C41 C42 -0.4(9) . . . . ?
C40 C41 C42 C37 1.4(8) . . . . ?
C38 C37 C42 C41 -0.4(8) . . . . ?
C36 C37 C42 C41 173.9(5) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_KIK-0607-3
_database_code_depnum_ccdc_archive 'CCDC 2007775'
loop_
_audit_author_name
_audit_author_address
'Takeshi Yasui'
;Nagoya University
Japan
;
_audit_update_record             
;
2020-06-03 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H20 O3'
_chemical_formula_moiety         'C24 H20 O3'
_chemical_formula_weight         356.42
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   13.0170(6)
_cell_length_b                   10.8103(5)
_cell_length_c                   13.8173(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 110.376(2)
_cell_angle_gamma                90.0000
_cell_volume                     1822.68(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8208
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      67.95
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752.00
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.433
_exptl_absorpt_correction_T_max  0.934

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            19341
_diffrn_reflns_av_R_equivalents  0.1361
_diffrn_reflns_theta_max         68.230
_diffrn_reflns_theta_min         4.020
_diffrn_reflns_theta_full        67.687
_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
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3332
_reflns_number_gt                1156
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1887
_refine_ls_R_factor_gt           0.1038
_refine_ls_wR_factor_ref         0.3372
_refine_ls_wR_factor_gt          0.2601
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3332
_refine_ls_number_parameters     245
_refine_ls_goodness_of_fit_ref   0.881
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1829P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.3800(3) 0.0184(4) 0.3532(3) 0.0687(13) Uani 1 1 d . . . . .
O2 O 0.3075(3) -0.1686(5) 0.3503(3) 0.0708(13) Uani 1 1 d . . . . .
O4 O 0.4789(3) 0.2037(4) 0.6711(3) 0.0721(13) Uani 1 1 d . . . . .
H4 H 0.5320 0.2123 0.6504 0.086 Uiso 1 1 calc R U . . .
C1 C 0.2563(5) 0.4151(7) 0.4177(5) 0.0638(18) Uani 1 1 d . . . . .
H1 H 0.2010 0.3787 0.3603 0.077 Uiso 1 1 calc R U . . .
C2 C 0.3136(5) -0.0621(8) 0.3802(5) 0.0688(19) Uani 1 1 d . . . . .
C3 C 0.3743(5) 0.1398(6) 0.3937(5) 0.0662(18) Uani 1 1 d . . . . .
H3A H 0.3459 0.2006 0.3371 0.079 Uiso 1 1 calc R U . . .
H3B H 0.4475 0.1671 0.4400 0.079 Uiso 1 1 calc R U . . .
C4 C 0.2975(4) 0.1265(6) 0.4522(4) 0.0587(17) Uani 1 1 d . . . . .
C5 C 0.1557(4) 0.0467(6) 0.5465(4) 0.0526(16) Uani 1 1 d . . . . .
H5 H 0.1063 0.0209 0.5794 0.063 Uiso 1 1 calc R U . . .
C6 C 0.1898(4) -0.0393(6) 0.4896(4) 0.0538(16) Uani 1 1 d . . . . .
C7 C 0.1913(4) 0.1712(6) 0.5578(4) 0.0521(16) Uani 1 1 d . . . . .
C8 C 0.3030(5) 0.3447(6) 0.5073(5) 0.0604(17) Uani 1 1 d . . . . .
C9 C 0.2625(4) 0.2126(6) 0.5078(4) 0.0572(17) Uani 1 1 d . . . . .
C10 C 0.2624(4) 0.0053(6) 0.4439(4) 0.0563(17) Uani 1 1 d . . . . .
C11 C 0.1502(4) 0.2566(6) 0.6223(5) 0.0582(17) Uani 1 1 d . . . . .
C12 C 0.1462(4) 0.2151(6) 0.7159(4) 0.0591(17) Uani 1 1 d . . . . .
H12 H 0.1682 0.1330 0.7381 0.071 Uiso 1 1 calc R U . . .
C13 C 0.1100(5) 0.2936(6) 0.7777(5) 0.0622(18) Uani 1 1 d . . . . .
H13 H 0.1078 0.2657 0.8421 0.075 Uiso 1 1 calc R U . . .
C14 C 0.0773(5) 0.4131(7) 0.7435(5) 0.0669(19) Uani 1 1 d . . . . .
H14 H 0.0536 0.4670 0.7859 0.080 Uiso 1 1 calc R U . . .
C15 C 0.0782(4) 0.4553(6) 0.6500(5) 0.0582(17) Uani 1 1 d . . . . .
H15 H 0.0549 0.5370 0.6273 0.070 Uiso 1 1 calc R U . . .
C16 C 0.1140(4) 0.3761(6) 0.5893(4) 0.0594(17) Uani 1 1 d . . . . .
H16 H 0.1139 0.4038 0.5240 0.071 Uiso 1 1 calc R U . . .
C17 C 0.2876(5) 0.5354(7) 0.4096(5) 0.074(2) Uani 1 1 d . . . . .
H17 H 0.2529 0.5826 0.3490 0.088 Uiso 1 1 calc R U . . .
C18 C 0.3715(5) 0.5856(6) 0.4929(5) 0.0687(18) Uani 1 1 d . . . . .
H18 H 0.3955 0.6679 0.4892 0.082 Uiso 1 1 calc R U . . .
C19 C 0.4212(5) 0.5145(6) 0.5830(5) 0.0595(17) Uani 1 1 d . . . . .
H19 H 0.4789 0.5492 0.6393 0.071 Uiso 1 1 calc R U . . .
C20 C 0.3867(5) 0.3946(6) 0.5902(5) 0.0590(17) Uani 1 1 d . . . . .
C21 C 0.4407(5) 0.3202(7) 0.6869(5) 0.0631(18) Uani 1 1 d . . . . .
C22 C 0.5048(5) 0.3830(6) 0.7856(5) 0.0640(17) Uani 1 1 d . . . . .
H22A H 0.5088 0.4745 0.7857 0.077 Uiso 1 1 calc R U . . .
H22B H 0.5715 0.3411 0.8318 0.077 Uiso 1 1 calc R U . . .
C23 C 0.3951(5) 0.3240(7) 0.7712(4) 0.071(2) Uani 1 1 d . . . . .
H23A H 0.3947 0.2461 0.8088 0.086 Uiso 1 1 calc R U . . .
H23B H 0.3320 0.3794 0.7627 0.086 Uiso 1 1 calc R U . . .
C24 C 0.1447(5) -0.1696(6) 0.4763(5) 0.0644(18) Uani 1 1 d . . . . .
H24A H 0.1775 -0.2175 0.4342 0.077 Uiso 1 1 calc R U . . .
H24B H 0.1624 -0.2088 0.5441 0.077 Uiso 1 1 calc R U . . .
H24C H 0.0649 -0.1671 0.4419 0.077 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.367(7) . ?
O1 C3 1.439(6) . ?
O2 C2 1.217(7) . ?
O4 C21 1.398(7) . ?
O4 H4 0.8400 . ?
C1 C17 1.379(8) . ?
C1 C8 1.400(8) . ?
C1 H1 0.9500 . ?
C2 C10 1.469(8) . ?
C3 C4 1.494(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C10 1.380(8) . ?
C4 C9 1.381(7) . ?
C5 C6 1.386(7) . ?
C5 C7 1.414(7) . ?
C5 H5 0.9500 . ?
C6 C10 1.392(7) . ?
C6 C24 1.513(7) . ?
C7 C9 1.408(7) . ?
C7 C11 1.505(8) . ?
C8 C20 1.386(8) . ?
C8 C9 1.523(8) . ?
C11 C12 1.387(7) . ?
C11 C16 1.397(7) . ?
C12 C13 1.396(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.375(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.392(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.414(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.507(8) . ?
C21 C23 1.481(8) . ?
C21 C22 1.492(8) . ?
C22 C23 1.514(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C3 110.6(5) . . ?
C21 O4 H4 109.5 . . ?
C17 C1 C8 122.3(6) . . ?
C17 C1 H1 118.9 . . ?
C8 C1 H1 118.9 . . ?
O2 C2 O1 118.9(6) . . ?
O2 C2 C10 133.1(6) . . ?
O1 C2 C10 108.1(6) . . ?
O1 C3 C4 104.9(5) . . ?
O1 C3 H3A 110.8 . . ?
C4 C3 H3A 110.8 . . ?
O1 C3 H3B 110.8 . . ?
C4 C3 H3B 110.8 . . ?
H3A C3 H3B 108.8 . . ?
C10 C4 C9 121.4(5) . . ?
C10 C4 C3 108.1(5) . . ?
C9 C4 C3 130.4(6) . . ?
C6 C5 C7 122.9(5) . . ?
C6 C5 H5 118.5 . . ?
C7 C5 H5 118.5 . . ?
C5 C6 C10 115.2(6) . . ?
C5 C6 C24 120.4(5) . . ?
C10 C6 C24 124.3(6) . . ?
C9 C7 C5 119.7(6) . . ?
C9 C7 C11 121.7(6) . . ?
C5 C7 C11 118.6(5) . . ?
C20 C8 C1 119.6(6) . . ?
C20 C8 C9 122.3(6) . . ?
C1 C8 C9 118.0(6) . . ?
C4 C9 C7 117.4(6) . . ?
C4 C9 C8 116.6(5) . . ?
C7 C9 C8 126.0(6) . . ?
C4 C10 C6 123.3(6) . . ?
C4 C10 C2 108.3(5) . . ?
C6 C10 C2 128.4(6) . . ?
C12 C11 C16 119.0(6) . . ?
C12 C11 C7 119.4(6) . . ?
C16 C11 C7 121.6(6) . . ?
C11 C12 C13 120.3(6) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.1(6) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C13 121.7(6) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 118.5(6) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C15 C16 C11 121.4(6) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C1 C17 C18 118.1(7) . . ?
C1 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C17 C18 C19 120.2(6) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 120.7(6) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C8 C20 C19 119.1(6) . . ?
C8 C20 C21 121.0(6) . . ?
C19 C20 C21 120.0(6) . . ?
O4 C21 C23 114.2(6) . . ?
O4 C21 C22 115.9(5) . . ?
C23 C21 C22 61.2(4) . . ?
O4 C21 C20 115.1(5) . . ?
C23 C21 C20 119.4(5) . . ?
C22 C21 C20 120.5(6) . . ?
C21 C22 C23 59.0(4) . . ?
C21 C22 H22A 117.9 . . ?
C23 C22 H22A 117.9 . . ?
C21 C22 H22B 117.9 . . ?
C23 C22 H22B 117.9 . . ?
H22A C22 H22B 115.0 . . ?
C21 C23 C22 59.7(4) . . ?
C21 C23 H23A 117.8 . . ?
C22 C23 H23A 117.8 . . ?
C21 C23 H23B 117.8 . . ?
C22 C23 H23B 117.8 . . ?
H23A C23 H23B 114.9 . . ?
C6 C24 H24A 109.5 . . ?
C6 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C6 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 O1 C2 O2 178.7(6) . . . . ?
C3 O1 C2 C10 -1.5(7) . . . . ?
C2 O1 C3 C4 1.2(6) . . . . ?
O1 C3 C4 C10 -0.4(6) . . . . ?
O1 C3 C4 C9 179.2(6) . . . . ?
C7 C5 C6 C10 0.1(8) . . . . ?
C7 C5 C6 C24 -177.1(5) . . . . ?
C6 C5 C7 C9 1.5(8) . . . . ?
C6 C5 C7 C11 -179.3(5) . . . . ?
C17 C1 C8 C20 -2.6(9) . . . . ?
C17 C1 C8 C9 -179.8(5) . . . . ?
C10 C4 C9 C7 1.3(8) . . . . ?
C3 C4 C9 C7 -178.2(6) . . . . ?
C10 C4 C9 C8 -177.3(5) . . . . ?
C3 C4 C9 C8 3.2(9) . . . . ?
C5 C7 C9 C4 -2.2(8) . . . . ?
C11 C7 C9 C4 178.6(5) . . . . ?
C5 C7 C9 C8 176.4(5) . . . . ?
C11 C7 C9 C8 -2.8(9) . . . . ?
C20 C8 C9 C4 -102.6(7) . . . . ?
C1 C8 C9 C4 74.5(7) . . . . ?
C20 C8 C9 C7 78.8(8) . . . . ?
C1 C8 C9 C7 -104.1(7) . . . . ?
C9 C4 C10 C6 0.3(9) . . . . ?
C3 C4 C10 C6 179.9(5) . . . . ?
C9 C4 C10 C2 179.9(5) . . . . ?
C3 C4 C10 C2 -0.5(7) . . . . ?
C5 C6 C10 C4 -1.0(8) . . . . ?
C24 C6 C10 C4 176.1(5) . . . . ?
C5 C6 C10 C2 179.4(6) . . . . ?
C24 C6 C10 C2 -3.4(9) . . . . ?
O2 C2 C10 C4 -179.0(7) . . . . ?
O1 C2 C10 C4 1.2(7) . . . . ?
O2 C2 C10 C6 0.6(12) . . . . ?
O1 C2 C10 C6 -179.2(5) . . . . ?
C9 C7 C11 C12 -137.6(6) . . . . ?
C5 C7 C11 C12 43.2(7) . . . . ?
C9 C7 C11 C16 43.7(8) . . . . ?
C5 C7 C11 C16 -135.5(6) . . . . ?
C16 C11 C12 C13 -2.2(8) . . . . ?
C7 C11 C12 C13 179.0(5) . . . . ?
C11 C12 C13 C14 0.6(8) . . . . ?
C12 C13 C14 C15 0.9(9) . . . . ?
C13 C14 C15 C16 -0.7(8) . . . . ?
C14 C15 C16 C11 -1.1(8) . . . . ?
C12 C11 C16 C15 2.5(8) . . . . ?
C7 C11 C16 C15 -178.7(5) . . . . ?
C8 C1 C17 C18 2.4(9) . . . . ?
C1 C17 C18 C19 -0.8(9) . . . . ?
C17 C18 C19 C20 -0.6(9) . . . . ?
C1 C8 C20 C19 1.1(8) . . . . ?
C9 C8 C20 C19 178.2(5) . . . . ?
C1 C8 C20 C21 -178.5(5) . . . . ?
C9 C8 C20 C21 -1.4(8) . . . . ?
C18 C19 C20 C8 0.4(8) . . . . ?
C18 C19 C20 C21 180.0(5) . . . . ?
C8 C20 C21 O4 52.1(7) . . . . ?
C19 C20 C21 O4 -127.5(6) . . . . ?
C8 C20 C21 C23 -89.4(8) . . . . ?
C19 C20 C21 C23 91.1(7) . . . . ?
C8 C20 C21 C22 -161.3(5) . . . . ?
C19 C20 C21 C22 19.1(8) . . . . ?
O4 C21 C22 C23 -104.6(6) . . . . ?
C20 C21 C22 C23 109.1(6) . . . . ?
O4 C21 C23 C22 107.4(6) . . . . ?
C20 C21 C23 C22 -110.8(7) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O4 H4 O2 . . 3_656 2.922(7) 0.840 2.145 153.6 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_KIK-0522
_database_code_depnum_ccdc_archive 'CCDC 2007773'
loop_
_audit_author_name
_audit_author_address
'Takeshi Yasui'
;Nagoya University
Japan
;
_audit_update_record             
;
2020-06-03 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C19 H20 O3'
_chemical_formula_moiety         'C19 H20 O3'
_chemical_formula_weight         296.37
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.6683(12)
_cell_length_b                   8.3860(10)
_cell_length_c                   11.3586(14)
_cell_angle_alpha                90.0000
_cell_angle_beta                 110.379(8)
_cell_angle_gamma                90.0000
_cell_volume                     774.01(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2392
_cell_measurement_theta_min      4.15
_cell_measurement_theta_max      67.71
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316.00
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_T_max  0.934

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            8864
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_theta_max         68.208
_diffrn_reflns_theta_min         4.152
_diffrn_reflns_theta_full        67.687
_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 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2669
_reflns_number_gt                2179
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_max     0.877
_reflns_Friedel_fraction_full    0.881

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.0976
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2669
_refine_ls_number_parameters     200
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0558P)²+0.0150P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0080(18)
_refine_ls_abs_structure_details 
;
 Flack x determined using 770 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(13)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.6203(3) 1.0248(3) 0.1912(2) 0.0377(6) Uani 1 1 d . . . . .
O2 O 0.6690(3) 1.0340(3) 0.3981(2) 0.0432(7) Uani 1 1 d . . . . .
O3 O 1.3255(3) 0.7021(4) 0.0987(2) 0.0450(7) Uani 1 1 d . . . . .
C1 C 0.6333(4) 0.9082(4) 0.0992(3) 0.0324(8) Uani 1 1 d . . . . .
H1A H 0.6761 0.9585 0.0379 0.039 Uiso 1 1 calc R U . . .
H1B H 0.5251 0.8591 0.0534 0.039 Uiso 1 1 calc R U . . .
C2 C 0.7524(4) 0.7864(4) 0.1778(3) 0.0299(8) Uani 1 1 d . . . . .
C3 C 0.7316(4) 0.7940(4) 0.3007(3) 0.0296(8) Uani 1 1 d . . . . .
C4 C 0.6750(4) 0.9598(5) 0.3082(3) 0.0349(8) Uani 1 1 d . . . . .
C5 C 0.8756(4) 0.7169(4) 0.1489(3) 0.0280(7) Uani 1 1 d . . . . .
C6 C 0.8819(4) 0.7169(4) 0.0207(3) 0.0309(8) Uani 1 1 d . . . . .
C7 C 0.7389(5) 0.7103(5) -0.0854(3) 0.0349(8) Uani 1 1 d . . . . .
H7 H 0.6347 0.7106 -0.0752 0.042 Uiso 1 1 calc R U . . .
C8 C 0.7461(5) 0.7034(5) -0.2048(3) 0.0393(9) Uani 1 1 d . . . . .
H8 H 0.6474 0.6988 -0.2757 0.047 Uiso 1 1 calc R U . . .
C9 C 0.8975(5) 0.7031(5) -0.2216(3) 0.0396(9) Uani 1 1 d . . . . .
H9 H 0.9020 0.7010 -0.3040 0.048 Uiso 1 1 calc R U . . .
C10 C 1.0415(5) 0.7059(5) -0.1184(3) 0.0380(8) Uani 1 1 d . . . . .
H10 H 1.1448 0.7033 -0.1300 0.046 Uiso 1 1 calc R U . . .
C11 C 1.0352(4) 0.7125(5) 0.0028(3) 0.0311(8) Uani 1 1 d . . . . .
C12 C 1.1924(4) 0.7135(4) 0.1123(3) 0.0341(8) Uani 1 1 d . . . . .
C13 C 1.1791(4) 0.7300(5) 0.2396(3) 0.0345(8) Uani 1 1 d . . . . .
H13A H 1.1750 0.8445 0.2594 0.041 Uiso 1 1 calc R U . . .
H13B H 1.2782 0.6834 0.3032 0.041 Uiso 1 1 calc R U . . .
C14 C 1.0263(4) 0.6471(4) 0.2469(3) 0.0316(8) Uani 1 1 d . . . . .
H14A H 1.0324 0.5313 0.2322 0.038 Uiso 1 1 calc R U . . .
H14B H 1.0197 0.6622 0.3315 0.038 Uiso 1 1 calc R U . . .
C15 C 0.7261(4) 0.6883(4) 0.3875(3) 0.0300(8) Uani 1 1 d . . . . .
H15 H 0.7214 0.7354 0.4623 0.036 Uiso 1 1 calc R U . . .
C16 C 0.7259(4) 0.5075(4) 0.3890(3) 0.0302(8) Uani 1 1 d . . . . .
C17 C 0.6796(4) 0.4353(4) 0.2575(3) 0.0361(9) Uani 1 1 d . . . . .
H17A H 0.6814 0.3187 0.2637 0.043 Uiso 1 1 calc R U . . .
H17B H 0.5691 0.4708 0.2059 0.043 Uiso 1 1 calc R U . . .
H17C H 0.7589 0.4701 0.2189 0.043 Uiso 1 1 calc R U . . .
C18 C 0.8923(4) 0.4386(5) 0.4752(3) 0.0379(9) Uani 1 1 d . . . . .
H18A H 0.8869 0.3219 0.4734 0.045 Uiso 1 1 calc R U . . .
H18B H 0.9801 0.4742 0.4455 0.045 Uiso 1 1 calc R U . . .
H18C H 0.9153 0.4762 0.5613 0.045 Uiso 1 1 calc R U . . .
C19 C 0.5947(4) 0.4579(5) 0.4443(3) 0.0372(9) Uani 1 1 d . . . . .
H19A H 0.5896 0.3413 0.4473 0.045 Uiso 1 1 calc R U . . .
H19B H 0.6235 0.5011 0.5295 0.045 Uiso 1 1 calc R U . . .
H19C H 0.4873 0.4997 0.3915 0.045 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C4 1.359(4) . ?
O1 C1 1.464(4) . ?
O2 C4 1.212(4) . ?
O3 C12 1.220(4) . ?
C1 C2 1.504(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C5 1.354(4) . ?
C2 C3 1.470(4) . ?
C3 C15 1.339(4) . ?
C3 C4 1.487(5) . ?
C5 C6 1.475(4) . ?
C5 C14 1.509(4) . ?
C6 C7 1.397(4) . ?
C6 C11 1.414(5) . ?
C7 C8 1.381(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.397(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.491(4) . ?
C12 C13 1.496(5) . ?
C13 C14 1.524(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.516(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.529(4) . ?
C16 C19 1.536(5) . ?
C16 C18 1.546(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C4 O1 C1 110.1(3) . . ?
O1 C1 C2 103.7(3) . . ?
O1 C1 H1A 111.0 . . ?
C2 C1 H1A 111.0 . . ?
O1 C1 H1B 111.0 . . ?
C2 C1 H1B 111.0 . . ?
H1A C1 H1B 109.0 . . ?
C5 C2 C3 128.1(3) . . ?
C5 C2 C1 125.8(3) . . ?
C3 C2 C1 104.4(3) . . ?
C15 C3 C2 135.9(3) . . ?
C15 C3 C4 118.7(3) . . ?
C2 C3 C4 104.3(3) . . ?
O2 C4 O1 121.0(4) . . ?
O2 C4 C3 129.8(3) . . ?
O1 C4 C3 109.2(3) . . ?
C2 C5 C6 122.9(3) . . ?
C2 C5 C14 122.8(3) . . ?
C6 C5 C14 114.1(3) . . ?
C7 C6 C11 118.1(3) . . ?
C7 C6 C5 121.6(3) . . ?
C11 C6 C5 120.1(3) . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 120.2(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.2(4) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C6 120.3(3) . . ?
C10 C11 C12 119.0(3) . . ?
C6 C11 C12 120.7(3) . . ?
O3 C12 C11 121.5(3) . . ?
O3 C12 C13 121.6(3) . . ?
C11 C12 C13 116.8(3) . . ?
C12 C13 C14 111.8(3) . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C5 C14 C13 109.2(3) . . ?
C5 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
C5 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
C3 C15 C16 132.1(3) . . ?
C3 C15 H15 114.0 . . ?
C16 C15 H15 114.0 . . ?
C15 C16 C17 112.7(3) . . ?
C15 C16 C19 106.2(3) . . ?
C17 C16 C19 108.2(3) . . ?
C15 C16 C18 112.1(3) . . ?
C17 C16 C18 109.9(3) . . ?
C19 C16 C18 107.4(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C4 O1 C1 C2 -18.2(4) . . . . ?
O1 C1 C2 C5 -138.0(3) . . . . ?
O1 C1 C2 C3 27.9(3) . . . . ?
C5 C2 C3 C15 -54.7(6) . . . . ?
C1 C2 C3 C15 139.8(4) . . . . ?
C5 C2 C3 C4 138.2(4) . . . . ?
C1 C2 C3 C4 -27.3(3) . . . . ?
C1 O1 C4 O2 -177.1(3) . . . . ?
C1 O1 C4 C3 1.1(4) . . . . ?
C15 C3 C4 O2 25.1(6) . . . . ?
C2 C3 C4 O2 -165.1(4) . . . . ?
C15 C3 C4 O1 -152.9(3) . . . . ?
C2 C3 C4 O1 16.9(4) . . . . ?
C3 C2 C5 C6 179.7(3) . . . . ?
C1 C2 C5 C6 -17.7(5) . . . . ?
C3 C2 C5 C14 -6.4(6) . . . . ?
C1 C2 C5 C14 156.1(3) . . . . ?
C2 C5 C6 C7 -33.5(5) . . . . ?
C14 C5 C6 C7 152.2(4) . . . . ?
C2 C5 C6 C11 150.9(3) . . . . ?
C14 C5 C6 C11 -23.4(5) . . . . ?
C11 C6 C7 C8 -1.5(6) . . . . ?
C5 C6 C7 C8 -177.2(3) . . . . ?
C6 C7 C8 C9 -0.1(6) . . . . ?
C7 C8 C9 C10 1.6(6) . . . . ?
C8 C9 C10 C11 -1.4(6) . . . . ?
C9 C10 C11 C6 -0.2(6) . . . . ?
C9 C10 C11 C12 179.3(4) . . . . ?
C7 C6 C11 C10 1.6(6) . . . . ?
C5 C6 C11 C10 177.4(3) . . . . ?
C7 C6 C11 C12 -177.9(3) . . . . ?
C5 C6 C11 C12 -2.2(5) . . . . ?
C10 C11 C12 O3 -3.1(6) . . . . ?
C6 C11 C12 O3 176.4(4) . . . . ?
C10 C11 C12 C13 176.6(3) . . . . ?
C6 C11 C12 C13 -3.8(5) . . . . ?
O3 C12 C13 C14 -145.9(4) . . . . ?
C11 C12 C13 C14 34.3(4) . . . . ?
C2 C5 C14 C13 -121.4(3) . . . . ?
C6 C5 C14 C13 52.9(4) . . . . ?
C12 C13 C14 C5 -58.2(4) . . . . ?
C2 C3 C15 C16 -5.9(7) . . . . ?
C4 C3 C15 C16 159.9(4) . . . . ?
C3 C15 C16 C17 -17.9(5) . . . . ?
C3 C15 C16 C19 -136.3(4) . . . . ?
C3 C15 C16 C18 106.7(4) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_KIK-0575-pro
_database_code_depnum_ccdc_archive 'CCDC 2007774'
loop_
_audit_author_name
_audit_author_address
'Takeshi Yasui'
;Nagoya University
Japan
;
_audit_update_record             
;
2020-06-03 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21 H16 O3'
_chemical_formula_moiety         'C21 H16 O3'
_chemical_formula_weight         316.36
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.6092(3)
_cell_length_b                   8.1201(3)
_cell_length_c                   10.9799(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 116.4260(18)
_cell_angle_gamma                90.0000
_cell_volume                     767.22(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7311
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332.00
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.734
_exptl_absorpt_correction_T_max  0.929

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            8943
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_theta_max         68.214
_diffrn_reflns_theta_min         4.497
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2701
_reflns_number_gt                2602
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_max     0.912
_reflns_Friedel_fraction_full    0.920

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0800
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2701
_refine_ls_number_parameters     218
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0378P)²+0.1740P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0050(11)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1098 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(8)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.63014(19) 0.3835(3) 0.21277(16) 0.0360(4) Uani 1 1 d . . . . .
O2 O 0.4884(2) 0.4638(3) -0.00032(18) 0.0358(4) Uani 1 1 d . . . . .
O3 O -0.0226(2) -0.0351(2) -0.31130(18) 0.0407(5) Uani 1 1 d . . . . .
C1 C 0.6119(3) 0.2982(4) 0.3205(2) 0.0346(6) Uani 1 1 d . . . . .
H1A H 0.6517 0.3662 0.4040 0.042 Uiso 1 1 calc R U . . .
H1B H 0.6689 0.1923 0.3417 0.042 Uiso 1 1 calc R U . . .
C2 C 0.4399(3) 0.2691(3) 0.2673(2) 0.0293(5) Uani 1 1 d . . . . .
C3 C 0.3699(3) 0.3084(3) 0.1218(2) 0.0285(5) Uani 1 1 d . . . . .
C4 C 0.4929(3) 0.3966(3) 0.0987(2) 0.0312(5) Uani 1 1 d . . . . .
C5 C 0.2306(3) 0.2591(3) 0.0211(2) 0.0275(5) Uani 1 1 d . . . . .
C6 C 0.1562(2) 0.3316(3) -0.1164(2) 0.0264(5) Uani 1 1 d . . . . .
C7 C 0.1595(3) 0.5015(3) -0.1382(3) 0.0299(5) Uani 1 1 d . . . . .
H7 H 0.2169 0.5714 -0.0631 0.036 Uiso 1 1 calc R U . . .
C8 C 0.0812(3) 0.5693(3) -0.2662(3) 0.0319(6) Uani 1 1 d . . . . .
H8 H 0.0847 0.6849 -0.2781 0.038 Uiso 1 1 calc R U . . .
C9 C -0.0033(3) 0.4689(4) -0.3783(3) 0.0342(6) Uani 1 1 d . . . . .
H9 H -0.0555 0.5153 -0.4668 0.041 Uiso 1 1 calc R U . . .
C10 C -0.0103(3) 0.3019(3) -0.3594(2) 0.0311(6) Uani 1 1 d . . . . .
H10 H -0.0678 0.2330 -0.4353 0.037 Uiso 1 1 calc R U . . .
C11 C 0.0662(3) 0.2329(3) -0.2300(2) 0.0268(5) Uani 1 1 d . . . . .
C12 C 0.0493(3) 0.0527(3) -0.2132(2) 0.0287(5) Uani 1 1 d . . . . .
C13 C 0.1234(3) -0.0143(3) -0.0711(2) 0.0300(5) Uani 1 1 d . . . . .
H13A H 0.2267 -0.0596 -0.0521 0.036 Uiso 1 1 calc R U . . .
H13B H 0.0590 -0.1063 -0.0652 0.036 Uiso 1 1 calc R U . . .
C14 C 0.1434(3) 0.1135(3) 0.0388(2) 0.0297(5) Uani 1 1 d . . . . .
H14A H 0.0405 0.1491 0.0293 0.036 Uiso 1 1 calc R U . . .
H14B H 0.2023 0.0650 0.1304 0.036 Uiso 1 1 calc R U . . .
C15 C 0.3644(3) 0.2459(3) 0.3438(2) 0.0311(6) Uani 1 1 d . . . . .
H15 H 0.2547 0.2337 0.2963 0.037 Uiso 1 1 calc R U . . .
C16 C 0.4330(3) 0.2374(3) 0.4928(2) 0.0292(5) Uani 1 1 d . . . . .
C17 C 0.3435(3) 0.2932(3) 0.5564(2) 0.0314(5) Uani 1 1 d . . . . .
H17 H 0.2386 0.3249 0.5022 0.038 Uiso 1 1 calc R U . . .
C18 C 0.4054(3) 0.3028(3) 0.6966(2) 0.0319(6) Uani 1 1 d . . . . .
H18 H 0.3440 0.3437 0.7380 0.038 Uiso 1 1 calc R U . . .
C19 C 0.5564(3) 0.2528(3) 0.7764(2) 0.0325(6) Uani 1 1 d . . . . .
H19 H 0.5997 0.2608 0.8726 0.039 Uiso 1 1 calc R U . . .
C20 C 0.6447(3) 0.1911(4) 0.7157(3) 0.0358(6) Uani 1 1 d . . . . .
H20 H 0.7476 0.1537 0.7707 0.043 Uiso 1 1 calc R U . . .
C21 C 0.5839(3) 0.1835(3) 0.5751(2) 0.0343(6) Uani 1 1 d . . . . .
H21 H 0.6456 0.1411 0.5346 0.041 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C4 1.360(3) . ?
O1 C1 1.447(3) . ?
O2 C4 1.200(3) . ?
O3 C12 1.217(3) . ?
C1 C2 1.507(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C15 1.346(3) . ?
C2 C3 1.466(3) . ?
C3 C5 1.363(3) . ?
C3 C4 1.497(3) . ?
C5 C6 1.476(3) . ?
C5 C14 1.511(4) . ?
C6 C7 1.403(4) . ?
C6 C11 1.409(3) . ?
C7 C8 1.380(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.493(4) . ?
C12 C13 1.500(3) . ?
C13 C14 1.538(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.468(3) . ?
C15 H15 0.9500 . ?
C16 C21 1.395(4) . ?
C16 C17 1.402(3) . ?
C17 C18 1.385(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 H21 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
C4 O1 C1 111.68(18) . . ?
O1 C1 C2 105.63(19) . . ?
O1 C1 H1A 110.6 . . ?
C2 C1 H1A 110.6 . . ?
O1 C1 H1B 110.6 . . ?
C2 C1 H1B 110.6 . . ?
H1A C1 H1B 108.7 . . ?
C15 C2 C3 126.7(2) . . ?
C15 C2 C1 125.7(2) . . ?
C3 C2 C1 106.27(19) . . ?
C5 C3 C2 128.9(2) . . ?
C5 C3 C4 124.5(2) . . ?
C2 C3 C4 106.0(2) . . ?
O2 C4 O1 119.9(2) . . ?
O2 C4 C3 131.2(2) . . ?
O1 C4 C3 108.8(2) . . ?
C3 C5 C6 124.5(2) . . ?
C3 C5 C14 121.7(2) . . ?
C6 C5 C14 113.6(2) . . ?
C7 C6 C11 117.4(2) . . ?
C7 C6 C5 122.0(2) . . ?
C11 C6 C5 120.3(2) . . ?
C8 C7 C6 121.5(2) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 120.3(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 119.3(2) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.7(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C6 120.7(2) . . ?
C10 C11 C12 118.9(2) . . ?
C6 C11 C12 120.4(2) . . ?
O3 C12 C11 121.0(2) . . ?
O3 C12 C13 121.9(2) . . ?
C11 C12 C13 117.2(2) . . ?
C12 C13 C14 114.0(2) . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C5 C14 C13 108.03(19) . . ?
C5 C14 H14A 110.1 . . ?
C13 C14 H14A 110.1 . . ?
C5 C14 H14B 110.1 . . ?
C13 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
C2 C15 C16 127.1(2) . . ?
C2 C15 H15 116.5 . . ?
C16 C15 H15 116.5 . . ?
C21 C16 C17 118.0(2) . . ?
C21 C16 C15 123.9(2) . . ?
C17 C16 C15 117.9(2) . . ?
C18 C17 C16 121.2(2) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 119.9(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 119.8(2) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 120.4(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.6(2) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?

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
C4 O1 C1 C2 -5.1(3) . . . . ?
O1 C1 C2 C15 -156.1(3) . . . . ?
O1 C1 C2 C3 11.3(3) . . . . ?
C15 C2 C3 C5 -33.9(4) . . . . ?
C1 C2 C3 C5 158.8(3) . . . . ?
C15 C2 C3 C4 154.2(3) . . . . ?
C1 C2 C3 C4 -13.0(3) . . . . ?
C1 O1 C4 O2 -179.7(2) . . . . ?
C1 O1 C4 C3 -3.2(3) . . . . ?
C5 C3 C4 O2 14.0(5) . . . . ?
C2 C3 C4 O2 -173.7(3) . . . . ?
C5 C3 C4 O1 -162.0(2) . . . . ?
C2 C3 C4 O1 10.3(3) . . . . ?
C2 C3 C5 C6 166.9(2) . . . . ?
C4 C3 C5 C6 -22.6(4) . . . . ?
C2 C3 C5 C14 -17.7(4) . . . . ?
C4 C3 C5 C14 152.8(2) . . . . ?
C3 C5 C6 C7 -39.5(3) . . . . ?
C14 C5 C6 C7 144.8(2) . . . . ?
C3 C5 C6 C11 146.6(2) . . . . ?
C14 C5 C6 C11 -29.2(3) . . . . ?
C11 C6 C7 C8 -1.7(3) . . . . ?
C5 C6 C7 C8 -175.8(2) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C7 C8 C9 C10 1.3(4) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 C6 -2.0(3) . . . . ?
C9 C10 C11 C12 177.1(2) . . . . ?
C7 C6 C11 C10 2.8(3) . . . . ?
C5 C6 C11 C10 177.1(2) . . . . ?
C7 C6 C11 C12 -176.2(2) . . . . ?
C5 C6 C11 C12 -2.0(3) . . . . ?
C10 C11 C12 O3 4.1(3) . . . . ?
C6 C11 C12 O3 -176.8(2) . . . . ?
C10 C11 C12 C13 -175.5(2) . . . . ?
C6 C11 C12 C13 3.7(3) . . . . ?
O3 C12 C13 C14 -154.1(2) . . . . ?
C11 C12 C13 C14 25.4(3) . . . . ?
C3 C5 C14 C13 -120.3(2) . . . . ?
C6 C5 C14 C13 55.6(3) . . . . ?
C12 C13 C14 C5 -54.0(3) . . . . ?
C3 C2 C15 C16 -167.5(3) . . . . ?
C1 C2 C15 C16 -2.7(4) . . . . ?
C2 C15 C16 C21 -28.4(4) . . . . ?
C2 C15 C16 C17 148.9(3) . . . . ?
C21 C16 C17 C18 3.3(4) . . . . ?
C15 C16 C17 C18 -174.1(2) . . . . ?
C16 C17 C18 C19 -1.7(4) . . . . ?
C17 C18 C19 C20 -0.9(4) . . . . ?
C18 C19 C20 C21 1.8(4) . . . . ?
C19 C20 C21 C16 -0.2(4) . . . . ?
C17 C16 C21 C20 -2.4(4) . . . . ?
C15 C16 C21 C20 174.9(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_KIK-0744
_database_code_depnum_ccdc_archive 'CCDC 2007776'
loop_
_audit_author_name
_audit_author_address
'Takeshi Yasui'
;Nagoya University
Japan
;
_audit_update_record             
;
2020-06-03 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C22 H18 O3'
_chemical_formula_moiety         'C22 H18 O3'
_chemical_formula_weight         330.38
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   15.8736(5)
_cell_length_b                   9.6592(3)
_cell_length_c                   10.7426(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.450(2)
_cell_angle_gamma                90.0000
_cell_volume                     1644.14(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10728
_cell_measurement_theta_min      4.13
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696.00
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.406
_exptl_absorpt_correction_T_max  0.868

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            17148
_diffrn_reflns_av_R_equivalents  0.1009
_diffrn_reflns_theta_max         68.224
_diffrn_reflns_theta_min         5.364
_diffrn_reflns_theta_full        67.687
_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
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3013
_reflns_number_gt                2014
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0773
_refine_ls_wR_factor_ref         0.3302
_refine_ls_wR_factor_gt          0.2382
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3013
_refine_ls_number_parameters     226
_refine_ls_goodness_of_fit_ref   1.268
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1852P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.49
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.06008(17) 0.3856(3) 0.4474(2) 0.0410(8) Uani 1 1 d . . . . .
O2 O 0.12444(18) 0.3301(3) 0.6305(2) 0.0443(8) Uani 1 1 d . . . . .
O3 O 0.32518(17) 0.3083(3) -0.0364(2) 0.0423(8) Uani 1 1 d . . . . .
C1 C 0.0762(2) 0.4720(4) 0.3395(4) 0.0372(10) Uani 1 1 d . . . . .
H1A H 0.0443 0.5600 0.3418 0.045 Uiso 1 1 calc R U . . .
H1B H 0.0599 0.4231 0.2607 0.045 Uiso 1 1 calc R U . . .
C2 C 0.1706(2) 0.4988(4) 0.3509(3) 0.0329(9) Uani 1 1 d . . . . .
C3 C 0.1957(2) 0.4722(4) 0.4833(3) 0.0326(9) Uani 1 1 d . . . . .
C4 C 0.1271(3) 0.3894(4) 0.5315(3) 0.0378(10) Uani 1 1 d . . . . .
C5 C 0.2182(2) 0.5129(4) 0.2516(3) 0.0304(9) Uani 1 1 d . . . . .
C6 C 0.1803(2) 0.5280(4) 0.1228(3) 0.0339(9) Uani 1 1 d . . . . .
C7 C 0.1109(2) 0.6121(4) 0.0944(4) 0.0373(10) Uani 1 1 d . . . . .
H7 H 0.0863 0.6619 0.1592 0.045 Uiso 1 1 calc R U . . .
C8 C 0.0766(3) 0.6247(4) -0.0275(4) 0.0414(11) Uani 1 1 d . . . . .
H8 H 0.0296 0.6840 -0.0457 0.050 Uiso 1 1 calc R U . . .
C9 C 0.1114(3) 0.5502(4) -0.1226(3) 0.0392(10) Uani 1 1 d . . . . .
H9 H 0.0882 0.5575 -0.2059 0.047 Uiso 1 1 calc R U . . .
C10 C 0.1798(2) 0.4657(4) -0.0952(3) 0.0357(10) Uani 1 1 d . . . . .
H10 H 0.2026 0.4137 -0.1603 0.043 Uiso 1 1 calc R U . . .
C11 C 0.2164(2) 0.4543(4) 0.0250(3) 0.0297(9) Uani 1 1 d . . . . .
C12 C 0.2935(2) 0.3715(4) 0.0478(3) 0.0317(9) Uani 1 1 d . . . . .
C13 C 0.3328(2) 0.3680(4) 0.1802(3) 0.0335(9) Uani 1 1 d . . . . .
H13A H 0.3948 0.3601 0.1771 0.040 Uiso 1 1 calc R U . . .
H13B H 0.3126 0.2842 0.2225 0.040 Uiso 1 1 calc R U . . .
C14 C 0.3126(2) 0.4953(4) 0.2579(3) 0.0336(9) Uani 1 1 d . . . . .
H14A H 0.3342 0.4822 0.3455 0.040 Uiso 1 1 calc R U . . .
H14B H 0.3396 0.5785 0.2244 0.040 Uiso 1 1 calc R U . . .
C15 C 0.2604(2) 0.5142(4) 0.5617(3) 0.0341(9) Uani 1 1 d . . . . .
H15 H 0.2622 0.4723 0.6418 0.041 Uiso 1 1 calc R U . . .
C16 C 0.3284(2) 0.6138(4) 0.5438(3) 0.0341(9) Uani 1 1 d . . . . .
C17 C 0.4098(3) 0.5932(4) 0.6036(3) 0.0362(10) Uani 1 1 d . . . . .
C18 C 0.4708(3) 0.6917(4) 0.5852(3) 0.0412(10) Uani 1 1 d . . . . .
H18 H 0.5255 0.6794 0.6244 0.049 Uiso 1 1 calc R U . . .
C19 C 0.4553(3) 0.8070(4) 0.5121(4) 0.0434(10) Uani 1 1 d . . . . .
H19 H 0.4988 0.8728 0.5016 0.052 Uiso 1 1 calc R U . . .
C20 C 0.3753(3) 0.8269(4) 0.4534(4) 0.0409(10) Uani 1 1 d . . . . .
H20 H 0.3642 0.9055 0.4017 0.049 Uiso 1 1 calc R U . . .
C21 C 0.3126(3) 0.7314(4) 0.4713(3) 0.0389(10) Uani 1 1 d . . . . .
H21 H 0.2577 0.7461 0.4335 0.047 Uiso 1 1 calc R U . . .
C22 C 0.4309(3) 0.4657(4) 0.6791(4) 0.0458(11) Uani 1 1 d . . . . .
H22A H 0.3804 0.4077 0.6824 0.055 Uiso 1 1 calc R U . . .
H22B H 0.4753 0.4137 0.6402 0.055 Uiso 1 1 calc R U . . .
H22C H 0.4506 0.4926 0.7638 0.055 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C4 1.355(4) . ?
O1 C1 1.463(4) . ?
O2 C4 1.211(4) . ?
O3 C12 1.224(4) . ?
C1 C2 1.519(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C5 1.351(6) . ?
C2 C3 1.476(5) . ?
C3 C15 1.351(5) . ?
C3 C4 1.470(5) . ?
C5 C6 1.483(5) . ?
C5 C14 1.504(5) . ?
C6 C7 1.387(5) . ?
C6 C11 1.419(5) . ?
C7 C8 1.393(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.470(5) . ?
C12 C13 1.519(4) . ?
C13 C14 1.531(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.467(5) . ?
C15 H15 0.9500 . ?
C16 C21 1.392(5) . ?
C16 C17 1.421(5) . ?
C17 C18 1.381(6) . ?
C17 C22 1.501(5) . ?
C18 C19 1.377(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.396(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.380(6) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C4 O1 C1 110.2(3) . . ?
O1 C1 C2 104.6(3) . . ?
O1 C1 H1A 110.8 . . ?
C2 C1 H1A 110.8 . . ?
O1 C1 H1B 110.8 . . ?
C2 C1 H1B 110.8 . . ?
H1A C1 H1B 108.9 . . ?
C5 C2 C3 130.3(4) . . ?
C5 C2 C1 123.4(3) . . ?
C3 C2 C1 104.8(3) . . ?
C15 C3 C4 119.7(3) . . ?
C15 C3 C2 134.4(4) . . ?
C4 C3 C2 105.7(3) . . ?
O2 C4 O1 120.3(4) . . ?
O2 C4 C3 129.3(3) . . ?
O1 C4 C3 110.4(3) . . ?
C2 C5 C6 122.1(3) . . ?
C2 C5 C14 123.8(3) . . ?
C6 C5 C14 113.6(3) . . ?
C7 C6 C11 118.8(3) . . ?
C7 C6 C5 122.4(3) . . ?
C11 C6 C5 118.8(3) . . ?
C6 C7 C8 121.3(4) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 119.6(4) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 121.8(4) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C6 118.9(3) . . ?
C10 C11 C12 119.7(3) . . ?
C6 C11 C12 121.3(3) . . ?
O3 C12 C11 121.6(3) . . ?
O3 C12 C13 121.1(3) . . ?
C11 C12 C13 117.3(3) . . ?
C12 C13 C14 113.9(3) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C5 C14 C13 107.9(3) . . ?
C5 C14 H14A 110.1 . . ?
C13 C14 H14A 110.1 . . ?
C5 C14 H14B 110.1 . . ?
C13 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
C3 C15 C16 130.8(4) . . ?
C3 C15 H15 114.6 . . ?
C16 C15 H15 114.6 . . ?
C21 C16 C17 119.7(4) . . ?
C21 C16 C15 119.9(3) . . ?
C17 C16 C15 120.3(3) . . ?
C18 C17 C16 117.7(4) . . ?
C18 C17 C22 120.5(4) . . ?
C16 C17 C22 121.7(4) . . ?
C19 C18 C17 122.4(4) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C18 C19 C20 119.7(4) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 119.3(4) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C16 121.1(4) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C4 O1 C1 C2 15.0(4) . . . . ?
O1 C1 C2 C5 146.9(4) . . . . ?
O1 C1 C2 C3 -20.4(4) . . . . ?
C5 C2 C3 C15 37.7(7) . . . . ?
C1 C2 C3 C15 -156.2(4) . . . . ?
C5 C2 C3 C4 -147.5(4) . . . . ?
C1 C2 C3 C4 18.6(4) . . . . ?
C1 O1 C4 O2 176.2(4) . . . . ?
C1 O1 C4 C3 -3.4(4) . . . . ?
C15 C3 C4 O2 -13.9(7) . . . . ?
C2 C3 C4 O2 170.4(4) . . . . ?
C15 C3 C4 O1 165.7(3) . . . . ?
C2 C3 C4 O1 -10.0(4) . . . . ?
C3 C2 C5 C6 174.8(3) . . . . ?
C1 C2 C5 C6 10.9(6) . . . . ?
C3 C2 C5 C14 3.6(6) . . . . ?
C1 C2 C5 C14 -160.2(4) . . . . ?
C2 C5 C6 C7 42.7(6) . . . . ?
C14 C5 C6 C7 -145.3(4) . . . . ?
C2 C5 C6 C11 -137.6(4) . . . . ?
C14 C5 C6 C11 34.4(5) . . . . ?
C11 C6 C7 C8 0.1(6) . . . . ?
C5 C6 C7 C8 179.8(4) . . . . ?
C6 C7 C8 C9 1.1(6) . . . . ?
C7 C8 C9 C10 -0.5(6) . . . . ?
C8 C9 C10 C11 -1.2(6) . . . . ?
C9 C10 C11 C6 2.3(6) . . . . ?
C9 C10 C11 C12 -175.0(4) . . . . ?
C7 C6 C11 C10 -1.7(5) . . . . ?
C5 C6 C11 C10 178.5(3) . . . . ?
C7 C6 C11 C12 175.6(3) . . . . ?
C5 C6 C11 C12 -4.2(5) . . . . ?
C10 C11 C12 O3 -2.4(6) . . . . ?
C6 C11 C12 O3 -179.6(3) . . . . ?
C10 C11 C12 C13 177.4(3) . . . . ?
C6 C11 C12 C13 0.1(5) . . . . ?
O3 C12 C13 C14 154.0(4) . . . . ?
C11 C12 C13 C14 -25.8(5) . . . . ?
C2 C5 C14 C13 114.2(4) . . . . ?
C6 C5 C14 C13 -57.7(4) . . . . ?
C12 C13 C14 C5 53.3(4) . . . . ?
C4 C3 C15 C16 -169.0(4) . . . . ?
C2 C3 C15 C16 5.2(8) . . . . ?
C3 C15 C16 C21 35.4(6) . . . . ?
C3 C15 C16 C17 -146.7(4) . . . . ?
C21 C16 C17 C18 -0.9(5) . . . . ?
C15 C16 C17 C18 -178.8(3) . . . . ?
C21 C16 C17 C22 -177.8(4) . . . . ?
C15 C16 C17 C22 4.3(6) . . . . ?
C16 C17 C18 C19 0.0(6) . . . . ?
C22 C17 C18 C19 177.0(4) . . . . ?
C17 C18 C19 C20 -0.1(6) . . . . ?
C18 C19 C20 C21 1.0(6) . . . . ?
C19 C20 C21 C16 -1.8(6) . . . . ?
C17 C16 C21 C20 1.8(6) . . . . ?
C15 C16 C21 C20 179.7(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
