# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_ic22359
_database_code_depnum_ccdc_archive 'CCDC 2382209'
loop_
_audit_author_name
_audit_author_address
'Su-Ying Chien'
;Instrumentation Center, National Taiwan University, Taipei, Taiwan
Taiwan
;
_audit_update_record             
;
2024-09-06 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 O4'
_chemical_formula_weight         352.41

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.3493(7)
_cell_length_b                   10.3182(8)
_cell_length_c                   12.4869(10)
_cell_angle_alpha                111.527(3)
_cell_angle_beta                 96.606(3)
_cell_angle_gamma                104.002(3)
_cell_volume                     945.89(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2296
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      22.23

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.134
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7947
_exptl_absorpt_correction_T_max  0.9602
_exptl_absorpt_process_details   
; 
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19902
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.219
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5523
_reflns_number_gt                3186
_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       'Bruker Instrument Service vV6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker APEX4'
_computing_publication_material  'Bruker APEX4'
_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)+(0.0860P)²+0.0271P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5523
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1925
_refine_ls_wR_factor_gt          0.1580
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
O1 O 0.59896(14) 0.44708(12) 0.16843(9) 0.0375(3) Uani 1 1 d . . . . .
O2 O 0.85214(19) 0.60708(15) 0.45419(11) 0.0590(4) Uani 1 1 d . . . . .
O3 O 0.4341(2) 0.14129(16) 0.28830(16) 0.0737(5) Uani 1 1 d . . . . .
O4 O 0.48606(17) 0.62689(14) 0.27286(11) 0.0471(3) Uani 1 1 d . . . . .
C1 C 0.6844(2) 0.42787(18) 0.26549(14) 0.0355(4) Uani 1 1 d . . . . .
C2 C 0.5447(2) 0.39475(18) 0.33481(15) 0.0392(4) Uani 1 1 d . . . . .
H2 H 0.570891 0.480326 0.412644 0.047 Uiso 1 1 calc R U . . .
C3 C 0.3838(2) 0.3871(2) 0.25891(16) 0.0457(4) Uani 1 1 d . . . . .
H3A H 0.321191 0.284842 0.203414 0.055 Uiso 1 1 calc R U . . .
H3B H 0.308713 0.427901 0.308558 0.055 Uiso 1 1 calc R U . . .
C4 C 0.4463(2) 0.47868(19) 0.19308(15) 0.0408(4) Uani 1 1 d . . . . .
C5 C 0.8273(2) 0.57018(19) 0.34740(15) 0.0405(4) Uani 1 1 d . . . . .
C6 C 0.9365(2) 0.66007(18) 0.29739(15) 0.0378(4) Uani 1 1 d . . . . .
C7 C 0.9472(2) 0.60802(19) 0.17967(15) 0.0421(4) Uani 1 1 d . . . . .
H7 H 0.881928 0.511199 0.126451 0.051 Uiso 1 1 calc R U . . .
C8 C 1.0529(2) 0.6972(2) 0.14001(17) 0.0476(5) Uani 1 1 d . . . . .
H8 H 1.060569 0.661135 0.059627 0.057 Uiso 1 1 calc R U . . .
C9 C 1.1470(3) 0.8381(2) 0.21632(18) 0.0507(5) Uani 1 1 d . . . . .
H9 H 1.218903 0.899041 0.188517 0.061 Uiso 1 1 calc R U . . .
C10 C 1.1367(3) 0.8903(2) 0.33284(18) 0.0546(5) Uani 1 1 d . . . . .
H10 H 1.201365 0.987524 0.385411 0.066 Uiso 1 1 calc R U . . .
C11 C 1.0326(2) 0.8020(2) 0.37377(16) 0.0479(5) Uani 1 1 d . . . . .
H11 H 1.026875 0.838431 0.454541 0.058 Uiso 1 1 calc R U . . .
C12 C 0.7604(2) 0.30345(18) 0.21457(14) 0.0371(4) Uani 1 1 d . . . . .
C13 C 0.8947(2) 0.2906(2) 0.28232(17) 0.0465(4) Uani 1 1 d . . . . .
H13 H 0.945398 0.363701 0.359954 0.056 Uiso 1 1 calc R U . . .
C14 C 0.9556(3) 0.1729(2) 0.2383(2) 0.0562(5) Uani 1 1 d . . . . .
H14 H 1.047026 0.165109 0.285941 0.067 Uiso 1 1 calc R U . . .
C15 C 0.8838(3) 0.0665(2) 0.1253(2) 0.0602(6) Uani 1 1 d . . . . .
H15 H 0.924636 -0.015092 0.095272 0.072 Uiso 1 1 calc R U . . .
C16 C 0.7528(3) 0.0795(2) 0.05652(19) 0.0575(5) Uani 1 1 d . . . . .
H16 H 0.704845 0.007426 -0.021829 0.069 Uiso 1 1 calc R U . . .
C17 C 0.6899(3) 0.19658(19) 0.10017(16) 0.0460(4) Uani 1 1 d . . . . .
H17 H 0.598731 0.203905 0.052033 0.055 Uiso 1 1 calc R U . . .
C18 C 0.5301(3) 0.2580(2) 0.35700(17) 0.0475(5) Uani 1 1 d . . . . .
C19 C 0.6382(3) 0.2759(2) 0.46903(18) 0.0618(6) Uani 1 1 d . . . . .
H19A H 0.578352 0.301537 0.533119 0.093 Uiso 1 1 calc R U . . .
H19B H 0.745063 0.353939 0.489136 0.093 Uiso 1 1 calc R U . . .
H19C H 0.661804 0.183891 0.458131 0.093 Uiso 1 1 calc R U . . .
C20 C 0.3275(3) 0.4398(2) 0.07731(18) 0.0557(5) Uani 1 1 d . . . . .
H20A H 0.379345 0.500598 0.038249 0.083 Uiso 1 1 calc R U . . .
H20B H 0.220380 0.457327 0.092466 0.083 Uiso 1 1 calc R U . . .
H20C H 0.305775 0.336301 0.026170 0.083 Uiso 1 1 calc R U . . .
C21 C 0.5509(3) 0.7340(2) 0.22851(18) 0.0515(5) Uani 1 1 d . . . . .
H21A H 0.459376 0.735539 0.171499 0.062 Uiso 1 1 calc R U . . .
H21B H 0.641356 0.710041 0.187462 0.062 Uiso 1 1 calc R U . . .
C22 C 0.6205(3) 0.8801(2) 0.3311(2) 0.0664(6) Uani 1 1 d . . . . .
H22A H 0.530473 0.902274 0.371696 0.100 Uiso 1 1 calc R U . . .
H22B H 0.663889 0.955607 0.302599 0.100 Uiso 1 1 calc R U . . .
H22C H 0.712674 0.878185 0.386063 0.100 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.430(2) . ?
O1 C1 1.4363(19) . ?
O2 C5 1.221(2) . ?
O3 C18 1.202(2) . ?
O4 C4 1.415(2) . ?
O4 C21 1.432(2) . ?
C1 C12 1.530(2) . ?
C1 C5 1.547(2) . ?
C1 C2 1.576(2) . ?
C2 C18 1.515(2) . ?
C2 C3 1.520(3) . ?
C3 C4 1.507(2) . ?
C4 C20 1.512(3) . ?
C5 C6 1.493(2) . ?
C6 C11 1.389(2) . ?
C6 C7 1.390(2) . ?
C7 C8 1.383(3) . ?
C8 C9 1.377(3) . ?
C9 C10 1.375(3) . ?
C10 C11 1.381(3) . ?
C12 C13 1.388(3) . ?
C12 C17 1.393(2) . ?
C13 C14 1.382(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.376(3) . ?
C16 C17 1.386(3) . ?
C18 C19 1.498(3) . ?
C21 C22 1.496(3) . ?

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 109.61(12) . . ?
C4 O4 C21 116.23(14) . . ?
O1 C1 C12 107.94(12) . . ?
O1 C1 C5 110.39(13) . . ?
C12 C1 C5 109.68(14) . . ?
O1 C1 C2 105.20(13) . . ?
C12 C1 C2 114.02(13) . . ?
C5 C1 C2 109.50(13) . . ?
C18 C2 C3 113.06(15) . . ?
C18 C2 C1 114.45(15) . . ?
C3 C2 C1 103.36(13) . . ?
C4 C3 C2 104.04(14) . . ?
O4 C4 O1 109.33(14) . . ?
O4 C4 C3 106.85(14) . . ?
O1 C4 C3 103.61(14) . . ?
O4 C4 C20 113.62(16) . . ?
O1 C4 C20 108.46(14) . . ?
C3 C4 C20 114.44(16) . . ?
O2 C5 C6 120.03(16) . . ?
O2 C5 C1 119.07(15) . . ?
C6 C5 C1 120.88(14) . . ?
C11 C6 C7 119.16(16) . . ?
C11 C6 C5 117.59(16) . . ?
C7 C6 C5 123.26(15) . . ?
C8 C7 C6 119.97(17) . . ?
C9 C8 C7 120.41(18) . . ?
C10 C9 C8 119.88(18) . . ?
C9 C10 C11 120.29(18) . . ?
C10 C11 C6 120.28(18) . . ?
C13 C12 C17 118.66(17) . . ?
C13 C12 C1 121.19(15) . . ?
C17 C12 C1 120.08(16) . . ?
C14 C13 C12 120.88(18) . . ?
C15 C14 C13 120.1(2) . . ?
C16 C15 C14 119.6(2) . . ?
C15 C16 C17 120.8(2) . . ?
C16 C17 C12 120.01(19) . . ?
O3 C18 C19 121.95(18) . . ?
O3 C18 C2 121.14(19) . . ?
C19 C18 C2 116.90(17) . . ?
O4 C21 C22 108.03(16) . . ?

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_ic22557
_database_code_depnum_ccdc_archive 'CCDC 2382211'
loop_
_audit_author_name
_audit_author_address
'Su-Ying Chien'
;Instrumentation Center, National Taiwan University, Taipei, Taiwan
Taiwan
;
_audit_update_record             
;
2024-09-06 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 F2 O4'
_chemical_formula_weight         374.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   17.2464(4)
_cell_length_b                   9.1025(2)
_cell_length_c                   25.1237(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.7066(8)
_cell_angle_gamma                90
_cell_volume                     3713.06(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9683
_cell_measurement_theta_min      5.58
_cell_measurement_theta_max      74.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.154
_exptl_absorpt_coefficient_mu    0.886
_shelx_estimated_absorpt_T_min   0.804
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6840
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_process_details   
; 
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53373
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.737
_diffrn_reflns_theta_max         74.599
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3790
_reflns_number_gt                3634
_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       'Bruker Instrument Service vV6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker APEX4'
_computing_publication_material  'Bruker APEX4'
_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)+(0.0600P)²+1.9298P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3790
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1050
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.32423(5) 0.38615(11) 0.87275(3) 0.0560(2) Uani 1 1 d . . . . .
F2 F 0.53087(7) 0.96070(10) 0.68857(5) 0.0747(3) Uani 1 1 d . . . . .
O1 O 0.23786(4) 0.51395(8) 0.60600(3) 0.02974(18) Uani 1 1 d . . . . .
O2 O 0.37595(7) 0.23401(9) 0.64429(4) 0.0520(3) Uani 1 1 d . . . . .
O3 O 0.38941(7) 0.58128(12) 0.50863(5) 0.0639(3) Uani 1 1 d . . . . .
O4 O 0.16536(5) 0.31849(9) 0.55135(4) 0.0406(2) Uani 1 1 d . . . . .
C1 C 0.32154(6) 0.47316(11) 0.61302(4) 0.0260(2) Uani 1 1 d . . . . .
C2 C 0.31943(7) 0.42330(12) 0.55271(4) 0.0306(2) Uani 1 1 d . . . . .
H2 H 0.316570 0.313607 0.550934 0.037 Uiso 1 1 calc R U . . .
C3 C 0.23745(7) 0.48458(13) 0.51450(5) 0.0350(3) Uani 1 1 d . . . . .
H3A H 0.242772 0.588436 0.504555 0.042 Uiso 1 1 calc R U . . .
H3B H 0.215199 0.426147 0.479389 0.042 Uiso 1 1 calc R U . . .
C4 C 0.18403(7) 0.47019(12) 0.55121(5) 0.0323(2) Uani 1 1 d . . . . .
C5 C 0.34665(7) 0.34527(11) 0.65604(5) 0.0309(2) Uani 1 1 d . . . . .
C6 C 0.33792(6) 0.36213(11) 0.71298(4) 0.0298(2) Uani 1 1 d . . . . .
C7 C 0.29530(8) 0.47657(14) 0.72769(5) 0.0382(3) Uani 1 1 d . . . . .
H7 H 0.269727 0.550145 0.700652 0.046 Uiso 1 1 calc R U . . .
C8 C 0.28995(8) 0.48380(15) 0.78151(5) 0.0435(3) Uani 1 1 d . . . . .
H8 H 0.260424 0.560950 0.791539 0.052 Uiso 1 1 calc R U . . .
C9 C 0.32835(7) 0.37679(15) 0.81998(5) 0.0403(3) Uani 1 1 d . . . . .
C10 C 0.37124(8) 0.26287(14) 0.80744(5) 0.0427(3) Uani 1 1 d . . . . .
H10 H 0.397051 0.190606 0.835002 0.051 Uiso 1 1 calc R U . . .
C11 C 0.37598(7) 0.25585(12) 0.75358(5) 0.0365(3) Uani 1 1 d . . . . .
H11 H 0.405466 0.177787 0.744074 0.044 Uiso 1 1 calc R U . . .
C12 C 0.37735(6) 0.60496(11) 0.63574(4) 0.0271(2) Uani 1 1 d . . . . .
C13 C 0.45984(7) 0.58591(12) 0.66825(5) 0.0338(2) Uani 1 1 d . . . . .
H13 H 0.480807 0.489535 0.678308 0.041 Uiso 1 1 calc R U . . .
C14 C 0.51188(7) 0.70579(15) 0.68616(5) 0.0424(3) Uani 1 1 d . . . . .
H14 H 0.568221 0.692817 0.708261 0.051 Uiso 1 1 calc R U . . .
C15 C 0.47980(9) 0.84309(14) 0.67111(6) 0.0458(3) Uani 1 1 d . . . . .
C16 C 0.39875(9) 0.86730(13) 0.63965(6) 0.0469(3) Uani 1 1 d . . . . .
H16 H 0.378333 0.964281 0.630328 0.056 Uiso 1 1 calc R U . . .
C17 C 0.34735(7) 0.74673(12) 0.62179(5) 0.0363(3) Uani 1 1 d . . . . .
H17 H 0.291084 0.761143 0.599793 0.044 Uiso 1 1 calc R U . . .
C18 C 0.39308(8) 0.47271(14) 0.53692(5) 0.0396(3) Uani 1 1 d . . . . .
C19 C 0.46820(8) 0.37836(18) 0.55659(6) 0.0510(3) Uani 1 1 d . . . . .
H19A H 0.460064 0.291264 0.532387 0.077 Uiso 1 1 calc R U . . .
H19B H 0.478096 0.347839 0.595735 0.077 Uiso 1 1 calc R U . . .
H19C H 0.515754 0.434047 0.554556 0.077 Uiso 1 1 calc R U . . .
C20 C 0.12212(9) 0.27539(16) 0.58822(6) 0.0514(3) Uani 1 1 d . . . . .
H20A H 0.147307 0.322310 0.625153 0.077 Uiso 1 1 calc R U . . .
H20B H 0.124957 0.168396 0.592792 0.077 Uiso 1 1 calc R U . . .
H20C H 0.064396 0.305855 0.572036 0.077 Uiso 1 1 calc R U . . .
C21 C 0.10915(7) 0.56817(15) 0.53608(6) 0.0449(3) Uani 1 1 d . . . . .
H21A H 0.070362 0.539354 0.499098 0.067 Uiso 1 1 calc R U . . .
H21B H 0.125902 0.670523 0.534553 0.067 Uiso 1 1 calc R U . . .
H21C H 0.082565 0.558271 0.564758 0.067 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
F1 C9 1.3542(14) . ?
F2 C15 1.3616(14) . ?
O1 C4 1.4331(12) . ?
O1 C1 1.4423(12) . ?
O2 C5 1.2119(14) . ?
O3 C18 1.2064(17) . ?
O4 C4 1.4181(13) . ?
O4 C20 1.4260(16) . ?
C1 C12 1.5235(14) . ?
C1 C5 1.5476(14) . ?
C1 C2 1.5702(14) . ?
C2 C18 1.5209(16) . ?
C2 C3 1.5218(16) . ?
C3 C4 1.5132(16) . ?
C4 C21 1.5088(16) . ?
C5 C6 1.4959(15) . ?
C6 C7 1.3948(16) . ?
C6 C11 1.3985(15) . ?
C7 C8 1.3874(17) . ?
C8 C9 1.3747(18) . ?
C9 C10 1.371(2) . ?
C10 C11 1.3843(18) . ?
C12 C17 1.3905(14) . ?
C12 C13 1.3920(15) . ?
C13 C14 1.3879(17) . ?
C14 C15 1.368(2) . ?
C15 C16 1.372(2) . ?
C16 C17 1.3869(17) . ?
C18 C19 1.4927(19) . ?

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 110.08(8) . . ?
C4 O4 C20 116.00(10) . . ?
O1 C1 C12 108.83(8) . . ?
O1 C1 C5 108.17(8) . . ?
C12 C1 C5 109.76(8) . . ?
O1 C1 C2 105.05(8) . . ?
C12 C1 C2 113.29(8) . . ?
C5 C1 C2 111.50(8) . . ?
C18 C2 C3 114.02(9) . . ?
C18 C2 C1 114.62(9) . . ?
C3 C2 C1 102.54(8) . . ?
C4 C3 C2 102.18(9) . . ?
O4 C4 O1 110.02(9) . . ?
O4 C4 C21 113.61(10) . . ?
O1 C4 C21 107.45(9) . . ?
O4 C4 C3 105.74(9) . . ?
O1 C4 C3 103.36(8) . . ?
C21 C4 C3 116.14(10) . . ?
O2 C5 C6 120.22(10) . . ?
O2 C5 C1 120.00(10) . . ?
C6 C5 C1 119.73(9) . . ?
C7 C6 C11 118.88(11) . . ?
C7 C6 C5 124.20(10) . . ?
C11 C6 C5 116.92(10) . . ?
C8 C7 C6 120.52(11) . . ?
C9 C8 C7 118.49(12) . . ?
F1 C9 C10 118.89(11) . . ?
F1 C9 C8 118.17(12) . . ?
C10 C9 C8 122.94(12) . . ?
C9 C10 C11 118.29(11) . . ?
C10 C11 C6 120.88(11) . . ?
C17 C12 C13 118.91(10) . . ?
C17 C12 C1 120.13(9) . . ?
C13 C12 C1 120.88(9) . . ?
C14 C13 C12 120.90(11) . . ?
C15 C14 C13 118.15(11) . . ?
F2 C15 C14 118.16(12) . . ?
F2 C15 C16 118.83(12) . . ?
C14 C15 C16 123.01(11) . . ?
C15 C16 C17 118.38(11) . . ?
C16 C17 C12 120.66(11) . . ?
O3 C18 C19 122.25(12) . . ?
O3 C18 C2 120.89(12) . . ?
C19 C18 C2 116.84(11) . . ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049



####################################################################### 
# 
# 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_ic22493
_database_code_depnum_ccdc_archive 'CCDC 2382210'
loop_
_audit_author_name
_audit_author_address
'Su-Ying Chien'
;Instrumentation Center, National Taiwan University, Taipei, Taiwan
Taiwan
;
_audit_update_record             
;
2024-09-06 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H22 O4'
_chemical_formula_weight         338.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   17.4908(4)
_cell_length_b                   8.9534(2)
_cell_length_c                   24.3196(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.5396(8)
_cell_angle_gamma                90
_cell_volume                     3610.85(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9801
_cell_measurement_theta_min      3.83
_cell_measurement_theta_max      74.44

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.181
_exptl_absorpt_coefficient_mu    0.691
_shelx_estimated_absorpt_T_min   0.772
_shelx_estimated_absorpt_T_max   0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8673
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_process_details   
; 
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39618
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.834
_diffrn_reflns_theta_max         74.425
_diffrn_reflns_theta_full        67.679
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3684
_reflns_number_gt                3486
_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       'Bruker Instrument Service vV6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker APEX4'
_computing_publication_material  'Bruker APEX4'
_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)+(0.0565P)²+1.9216P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3684
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
O1 O 0.38744(4) 0.74024(9) 0.39187(3) 0.03143(19) Uani 1 1 d . . . . .
O2 O 0.37096(5) 0.94543(10) 0.44629(4) 0.0423(2) Uani 1 1 d . . . . .
O3 O 0.62843(6) 0.66823(13) 0.49881(6) 0.0715(4) Uani 1 1 d . . . . .
O4 O 0.50403(6) 0.99356(10) 0.34740(4) 0.0486(2) Uani 1 1 d . . . . .
C1 C 0.38676(7) 0.78958(13) 0.44765(5) 0.0347(3) Uani 1 1 d . . . . .
C2 C 0.47337(7) 0.77117(13) 0.48543(5) 0.0374(3) Uani 1 1 d . . . . .
H2A H 0.485680 0.665636 0.497029 0.045 Uiso 1 1 calc R U . . .
H2B H 0.485550 0.834013 0.520665 0.045 Uiso 1 1 calc R U . . .
C3 C 0.51980(7) 0.82331(12) 0.44588(5) 0.0329(2) Uani 1 1 d . . . . .
H3 H 0.520217 0.935001 0.446011 0.039 Uiso 1 1 calc R U . . .
C4 C 0.46469(6) 0.76964(11) 0.38464(4) 0.0273(2) Uani 1 1 d . . . . .
C5 C 0.32552(9) 0.69673(18) 0.46410(6) 0.0508(3) Uani 1 1 d . . . . .
H5A H 0.272367 0.709886 0.435019 0.076 Uiso 1 1 calc R U . . .
H5B H 0.323355 0.728705 0.502117 0.076 Uiso 1 1 calc R U . . .
H5C H 0.341027 0.591219 0.465872 0.076 Uiso 1 1 calc R U . . .
C6 C 0.29439(9) 0.99113(18) 0.40845(7) 0.0574(4) Uani 1 1 d . . . . .
H6A H 0.252455 0.964286 0.425474 0.086 Uiso 1 1 calc R U . . .
H6B H 0.283633 0.941039 0.370920 0.086 Uiso 1 1 calc R U . . .
H6C H 0.294353 1.099543 0.402894 0.086 Uiso 1 1 calc R U . . .
C7 C 0.60675(7) 0.76940(15) 0.46456(6) 0.0442(3) Uani 1 1 d . . . . .
C8 C 0.66407(8) 0.8526(2) 0.44178(7) 0.0578(4) Uani 1 1 d . . . . .
H8A H 0.714210 0.795488 0.449630 0.087 Uiso 1 1 calc R U . . .
H8B H 0.675779 0.950140 0.460886 0.087 Uiso 1 1 calc R U . . .
H8C H 0.639916 0.866793 0.399858 0.087 Uiso 1 1 calc R U . . .
C9 C 0.45461(6) 0.89385(11) 0.33875(5) 0.0310(2) Uani 1 1 d . . . . .
C10 C 0.38505(7) 0.89007(12) 0.28368(5) 0.0324(2) Uani 1 1 d . . . . .
C11 C 0.37587(9) 1.01256(16) 0.24683(6) 0.0475(3) Uani 1 1 d . . . . .
H11 H 0.413412 1.092592 0.256971 0.057 Uiso 1 1 calc R U . . .
C12 C 0.31236(10) 1.0181(2) 0.19555(7) 0.0615(4) Uani 1 1 d . . . . .
H12 H 0.306139 1.102581 0.170867 0.074 Uiso 1 1 calc R U . . .
C13 C 0.25827(9) 0.9026(2) 0.18008(6) 0.0599(4) Uani 1 1 d . . . . .
H13 H 0.214705 0.907186 0.144803 0.072 Uiso 1 1 calc R U . . .
C14 C 0.26723(9) 0.7798(2) 0.21584(6) 0.0553(4) Uani 1 1 d . . . . .
H14 H 0.229906 0.699543 0.204977 0.066 Uiso 1 1 calc R U . . .
C15 C 0.33045(8) 0.77282(15) 0.26758(5) 0.0423(3) Uani 1 1 d . . . . .
H15 H 0.336402 0.687872 0.291994 0.051 Uiso 1 1 calc R U . . .
C16 C 0.49455(6) 0.62613(11) 0.36428(4) 0.0294(2) Uani 1 1 d . . . . .
C17 C 0.47199(8) 0.48839(13) 0.38071(5) 0.0397(3) Uani 1 1 d . . . . .
H17 H 0.436743 0.484269 0.403399 0.048 Uiso 1 1 calc R U . . .
C18 C 0.50061(10) 0.35728(14) 0.36418(6) 0.0506(3) Uani 1 1 d . . . . .
H18 H 0.484620 0.263682 0.375345 0.061 Uiso 1 1 calc R U . . .
C19 C 0.55230(10) 0.36216(15) 0.33154(6) 0.0530(4) Uani 1 1 d . . . . .
H19 H 0.572012 0.272059 0.320395 0.064 Uiso 1 1 calc R U . . .
C20 C 0.57531(9) 0.49818(16) 0.31509(6) 0.0496(3) Uani 1 1 d . . . . .
H20 H 0.611077 0.501437 0.292778 0.060 Uiso 1 1 calc R U . . .
C21 C 0.54636(7) 0.63032(13) 0.33106(5) 0.0378(3) Uani 1 1 d . . . . .
H21 H 0.561918 0.723586 0.319310 0.045 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4304(13) . ?
O1 C4 1.4410(12) . ?
O2 C1 1.4208(14) . ?
O2 C6 1.4226(16) . ?
O3 C7 1.2072(18) . ?
O4 C9 1.2136(14) . ?
C1 C5 1.5070(18) . ?
C1 C2 1.5103(16) . ?
C2 C3 1.5163(17) . ?
C3 C7 1.5209(16) . ?
C3 C4 1.5701(14) . ?
C4 C16 1.5276(14) . ?
C4 C9 1.5455(14) . ?
C7 C8 1.490(2) . ?
C9 C10 1.4963(15) . ?
C10 C15 1.3891(17) . ?
C10 C11 1.3929(17) . ?
C11 C12 1.382(2) . ?
C12 C13 1.371(3) . ?
C13 C14 1.380(2) . ?
C14 C15 1.3875(18) . ?
C16 C17 1.3916(16) . ?
C16 C21 1.3930(16) . ?
C17 C18 1.3849(17) . ?
C18 C19 1.381(2) . ?
C19 C20 1.381(2) . ?
C20 C21 1.3900(17) . ?

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
C1 O1 C4 110.50(8) . . ?
C1 O2 C6 115.70(11) . . ?
O2 C1 O1 109.97(9) . . ?
O2 C1 C5 113.49(10) . . ?
O1 C1 C5 107.60(10) . . ?
O2 C1 C2 105.75(9) . . ?
O1 C1 C2 103.54(9) . . ?
C5 C1 C2 115.99(11) . . ?
C1 C2 C3 102.49(9) . . ?
C2 C3 C7 113.53(10) . . ?
C2 C3 C4 102.50(9) . . ?
C7 C3 C4 116.11(9) . . ?
O1 C4 C16 108.45(8) . . ?
O1 C4 C9 108.87(8) . . ?
C16 C4 C9 110.08(8) . . ?
O1 C4 C3 104.88(8) . . ?
C16 C4 C3 113.26(8) . . ?
C9 C4 C3 111.07(8) . . ?
O3 C7 C8 122.05(12) . . ?
O3 C7 C3 120.61(13) . . ?
C8 C7 C3 117.23(12) . . ?
O4 C9 C10 120.23(10) . . ?
O4 C9 C4 119.52(10) . . ?
C10 C9 C4 120.25(9) . . ?
C15 C10 C11 119.04(12) . . ?
C15 C10 C9 124.04(10) . . ?
C11 C10 C9 116.92(11) . . ?
C12 C11 C10 120.26(14) . . ?
C13 C12 C11 120.46(14) . . ?
C12 C13 C14 119.87(13) . . ?
C13 C14 C15 120.36(14) . . ?
C14 C15 C10 119.99(13) . . ?
C17 C16 C21 119.11(10) . . ?
C17 C16 C4 119.66(10) . . ?
C21 C16 C4 121.19(10) . . ?
C18 C17 C16 120.41(12) . . ?
C19 C18 C17 120.21(13) . . ?
C18 C19 C20 119.93(11) . . ?
C19 C20 C21 120.27(13) . . ?
C20 C21 C16 120.07(12) . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.045



