# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_ic21619
_database_code_depnum_ccdc_archive 'CCDC 2280494'
loop_
_audit_author_name
_audit_author_address
'Su-Ying Chien'
;Instrumentation Center, National Taiwan University, Taipei, Taiwan
Taiwan
;
_audit_update_record             
;
2023-07-10 deposited with the CCDC.	2023-11-21 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            'C25 H25 N'
_chemical_formula_weight         339.46

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   7.7704(4)
_cell_length_b                   11.2784(5)
_cell_length_c                   11.4173(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.296(7)
_cell_angle_gamma                90
_cell_volume                     955.34(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4129
_cell_measurement_theta_min      4.0020
_cell_measurement_theta_max      78.3670

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.510
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.10453
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_reflns_number            10783
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.055
_diffrn_reflns_theta_max         67.993
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3500
_reflns_number_gt                2889
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1047P)²+0.0459P] 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     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1016 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.2(10)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3500
_refine_ls_number_parameters     237
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1947
_refine_ls_wR_factor_gt          0.1702
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
N1 N 0.2897(5) 0.5420(3) 0.2526(4) 0.0514(9) Uani 1 1 d . . . . .
C1 C 0.4549(5) 0.4155(4) 0.4939(4) 0.0461(9) Uani 1 1 d . . . . .
C2 C 0.3335(5) 0.5116(3) 0.4709(4) 0.0422(8) Uani 1 1 d . . . . .
C3 C 0.2688(5) 0.5523(4) 0.5649(4) 0.0445(9) Uani 1 1 d . . . . .
H3 H 0.186134 0.616620 0.548892 0.053 Uiso 1 1 calc R U . . .
C4 C 0.3209(6) 0.5019(4) 0.6815(4) 0.0498(10) Uani 1 1 d . . . . .
C5 C 0.4708(6) 0.4276(4) 0.7086(5) 0.0568(11) Uani 1 1 d . . . . .
H5 H 0.529174 0.405748 0.791213 0.068 Uiso 1 1 calc R U . . .
C6 C 0.5349(6) 0.3856(4) 0.6160(5) 0.0540(11) Uani 1 1 d . . . . .
H6 H 0.636974 0.334751 0.636456 0.065 Uiso 1 1 calc R U . . .
C7 C 0.4695(6) 0.3303(4) 0.3957(5) 0.0541(11) Uani 1 1 d . . . . .
H7A H 0.574501 0.277658 0.429601 0.065 Uiso 1 1 calc R U . . .
H7B H 0.490875 0.375595 0.327077 0.065 Uiso 1 1 calc R U . . .
C8 C 0.2940(7) 0.2515(5) 0.3446(5) 0.0602(12) Uani 1 1 d . . . . .
H8A H 0.223164 0.282173 0.263317 0.072 Uiso 1 1 calc R U . . .
H8B H 0.330328 0.169146 0.333187 0.072 Uiso 1 1 calc R U . . .
C9 C 0.1765(6) 0.2504(4) 0.4288(5) 0.0508(10) Uani 1 1 d . . . . .
C10 C 0.0295(5) 0.3266(4) 0.4075(5) 0.0519(10) Uani 1 1 d . . . . .
H10 H -0.029928 0.352117 0.326186 0.062 Uiso 1 1 calc R U . . .
C11 C -0.0321(5) 0.3662(4) 0.5039(5) 0.0542(11) Uani 1 1 d . . . . .
H11 H -0.133031 0.417853 0.487572 0.065 Uiso 1 1 calc R U . . .
C12 C 0.0531(6) 0.3306(5) 0.6225(5) 0.0581(12) Uani 1 1 d . . . . .
C13 C 0.1728(6) 0.2361(5) 0.6378(5) 0.0612(12) Uani 1 1 d . . . . .
H13 H 0.213645 0.198282 0.715510 0.073 Uiso 1 1 calc R U . . .
C14 C 0.2335(6) 0.1959(4) 0.5434(6) 0.0575(11) Uani 1 1 d . . . . .
H14 H 0.314607 0.130813 0.556317 0.069 Uiso 1 1 calc R U . . .
C15 C 0.0504(9) 0.4078(7) 0.7317(7) 0.0816(19) Uani 1 1 d . . . . .
H15A H 0.069285 0.356831 0.804981 0.098 Uiso 1 1 calc R U . . .
H15B H -0.069860 0.445069 0.714795 0.098 Uiso 1 1 calc R U . . .
C16 C 0.1968(7) 0.5070(5) 0.7603(5) 0.0604(12) Uani 1 1 d . . . . .
H16A H 0.136133 0.585185 0.749026 0.073 Uiso 1 1 calc R U . . .
H16B H 0.269658 0.500631 0.847423 0.073 Uiso 1 1 calc R U . . .
C17 C 0.2512(5) 0.5654(4) 0.3507(4) 0.0456(9) Uani 1 1 d . . . . .
H17 H 0.160385 0.623270 0.345455 0.055 Uiso 1 1 calc R U . . .
C18 C 0.1859(6) 0.6046(4) 0.1423(5) 0.0524(10) Uani 1 1 d . . . . .
H18 H 0.112860 0.668525 0.165316 0.063 Uiso 1 1 calc R U . . .
C19 C 0.0598(7) 0.5152(5) 0.0583(6) 0.0678(13) Uani 1 1 d . . . . .
H19A H 0.130520 0.448620 0.042138 0.102 Uiso 1 1 calc R U . . .
H19B H -0.004410 0.553813 -0.019245 0.102 Uiso 1 1 calc R U . . .
H19C H -0.027382 0.485927 0.098283 0.102 Uiso 1 1 calc R U . . .
C20 C 0.3089(6) 0.6586(4) 0.0762(4) 0.0496(9) Uani 1 1 d . . . . .
C21 C 0.4753(7) 0.6144(5) 0.0847(5) 0.0620(12) Uani 1 1 d . . . . .
H21 H 0.521346 0.549963 0.138436 0.074 Uiso 1 1 calc R U . . .
C22 C 0.5777(8) 0.6619(7) 0.0166(6) 0.0775(17) Uani 1 1 d . . . . .
H22 H 0.692624 0.628875 0.022968 0.093 Uiso 1 1 calc R U . . .
C23 C 0.5158(8) 0.7569(7) -0.0608(6) 0.0754(16) Uani 1 1 d . . . . .
H23 H 0.588025 0.790620 -0.106281 0.091 Uiso 1 1 calc R U . . .
C24 C 0.3477(9) 0.8015(6) -0.0707(6) 0.0761(16) Uani 1 1 d . . . . .
H24 H 0.301715 0.865725 -0.124782 0.091 Uiso 1 1 calc R U . . .
C25 C 0.2460(7) 0.7540(5) -0.0030(5) 0.0637(12) Uani 1 1 d . . . . .
H25 H 0.130604 0.786467 -0.009971 0.076 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
N1 C17 1.269(6) . ?
N1 C18 1.460(6) . ?
C1 C6 1.389(7) . ?
C1 C2 1.409(6) . ?
C1 C7 1.507(7) . ?
C2 C3 1.391(6) . ?
C2 C17 1.463(6) . ?
C3 C4 1.393(6) . ?
C4 C5 1.393(7) . ?
C4 C16 1.502(6) . ?
C5 C6 1.379(7) . ?
C7 C8 1.586(6) . ?
C8 C9 1.510(7) . ?
C9 C10 1.392(7) . ?
C9 C14 1.393(8) . ?
C10 C11 1.397(7) . ?
C11 C12 1.379(8) . ?
C12 C13 1.391(8) . ?
C12 C15 1.525(8) . ?
C13 C14 1.376(8) . ?
C15 C16 1.559(7) . ?
C18 C20 1.511(6) . ?
C18 C19 1.528(7) . ?
C20 C21 1.362(7) . ?
C20 C25 1.397(7) . ?
C21 C22 1.375(8) . ?
C22 C23 1.381(10) . ?
C23 C24 1.373(10) . ?
C24 C25 1.368(8) . ?

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
C17 N1 C18 116.5(4) . . ?
C6 C1 C2 116.7(4) . . ?
C6 C1 C7 118.8(4) . . ?
C2 C1 C7 123.1(4) . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 C17 115.4(4) . . ?
C1 C2 C17 125.2(4) . . ?
C2 C3 C4 122.3(4) . . ?
C3 C4 C5 116.3(4) . . ?
C3 C4 C16 120.1(4) . . ?
C5 C4 C16 122.2(4) . . ?
C6 C5 C4 120.4(5) . . ?
C5 C6 C1 122.0(4) . . ?
C1 C7 C8 112.6(4) . . ?
C9 C8 C7 112.7(4) . . ?
C10 C9 C14 116.9(5) . . ?
C10 C9 C8 120.3(5) . . ?
C14 C9 C8 121.2(4) . . ?
C9 C10 C11 121.0(5) . . ?
C12 C11 C10 120.3(4) . . ?
C11 C12 C13 117.0(5) . . ?
C11 C12 C15 121.2(6) . . ?
C13 C12 C15 120.4(6) . . ?
C14 C13 C12 121.8(5) . . ?
C13 C14 C9 120.2(5) . . ?
C12 C15 C16 113.2(4) . . ?
C4 C16 C15 113.9(4) . . ?
N1 C17 C2 126.1(4) . . ?
N1 C18 C20 110.9(4) . . ?
N1 C18 C19 108.0(4) . . ?
C20 C18 C19 109.6(4) . . ?
C21 C20 C25 118.0(5) . . ?
C21 C20 C18 123.0(4) . . ?
C25 C20 C18 118.8(4) . . ?
C20 C21 C22 120.9(5) . . ?
C21 C22 C23 120.9(6) . . ?
C24 C23 C22 118.6(5) . . ?
C25 C24 C23 120.3(6) . . ?
C24 C25 C20 121.2(5) . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_ic21545
_database_code_depnum_ccdc_archive 'CCDC 2280495'
loop_
_audit_author_name
_audit_author_address
'Su-Ying Chien'
;Instrumentation Center, National Taiwan University, Taipei, Taiwan
Taiwan
;
_audit_update_record             
;
2023-07-10 deposited with the CCDC.	2023-11-21 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            'C19 H18 O4'
_chemical_formula_weight         310.33

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.7133(2)
_cell_length_b                   11.0969(3)
_cell_length_c                   17.3223(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.5300(10)
_cell_angle_gamma                90
_cell_volume                     1481.23(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8538
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      30.44

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19568
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.180
_diffrn_reflns_theta_max         29.993
_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             4313
_reflns_number_gt                3009
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0747P)²+1.2808P] 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         4313
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1975
_refine_ls_wR_factor_gt          0.1569
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.4119(3) 0.62520(15) 0.53278(9) 0.0521(5) Uani 1 1 d . . . . .
O2 O 0.4892(2) 0.46272(13) 0.60232(9) 0.0458(4) Uani 1 1 d . . . . .
H2 H 0.513963 0.436822 0.558594 0.069 Uiso 1 1 calc R U . . .
O3 O 0.7480(3) 0.83926(18) 0.52944(11) 0.0632(5) Uani 1 1 d . . . . .
O4 O 0.8097(2) 0.66898(15) 0.59374(9) 0.0505(4) Uani 1 1 d . . . . .
C1 C 0.2765(3) 0.73026(18) 0.67486(12) 0.0365(4) Uani 1 1 d . . . . .
C2 C 0.3839(2) 0.62783(17) 0.67061(11) 0.0326(4) Uani 1 1 d . . . . .
C3 C 0.4658(3) 0.58109(17) 0.73773(11) 0.0323(4) Uani 1 1 d . . . . .
H3 H 0.540302 0.513356 0.733965 0.039 Uiso 1 1 calc R U . . .
C4 C 0.4407(3) 0.63160(17) 0.80994(12) 0.0356(4) Uani 1 1 d . . . . .
C5 C 0.3009(3) 0.7107(2) 0.81451(13) 0.0403(5) Uani 1 1 d . . . . .
H5 H 0.259517 0.731527 0.863607 0.048 Uiso 1 1 calc R U . . .
C6 C 0.2225(3) 0.75903(19) 0.74863(13) 0.0395(5) Uani 1 1 d . . . . .
H6 H 0.128635 0.813591 0.753422 0.047 Uiso 1 1 calc R U . . .
C7 C 0.2426(3) 0.8215(2) 0.61127(14) 0.0461(5) Uani 1 1 d . . . . .
H7A H 0.139906 0.870198 0.623656 0.055 Uiso 1 1 calc R U . . .
H7B H 0.214511 0.778157 0.562369 0.055 Uiso 1 1 calc R U . . .
C8 C 0.3996(3) 0.9088(2) 0.59877(15) 0.0513(6) Uani 1 1 d . . . . .
H8A H 0.453123 0.887992 0.549610 0.062 Uiso 1 1 calc R U . . .
H8B H 0.356059 0.992552 0.594456 0.062 Uiso 1 1 calc R U . . .
C9 C 0.5372(3) 0.90160(18) 0.66462(14) 0.0407(5) Uani 1 1 d . . . . .
C10 C 0.6788(3) 0.82229(18) 0.66293(12) 0.0361(4) Uani 1 1 d . . . . .
C11 C 0.7517(3) 0.77372(19) 0.73148(12) 0.0366(4) Uani 1 1 d . . . . .
H11 H 0.843910 0.717310 0.729092 0.044 Uiso 1 1 calc R U . . .
C12 C 0.6915(3) 0.8065(2) 0.80312(12) 0.0400(5) Uani 1 1 d . . . . .
C13 C 0.5800(3) 0.9058(2) 0.80380(14) 0.0462(5) Uani 1 1 d . . . . .
H13 H 0.556246 0.942572 0.851713 0.055 Uiso 1 1 calc R U . . .
C14 C 0.5037(3) 0.95155(19) 0.73651(15) 0.0455(5) Uani 1 1 d . . . . .
H14 H 0.426888 1.018236 0.739076 0.055 Uiso 1 1 calc R U . . .
C15 C 0.7169(3) 0.7240(3) 0.87189(13) 0.0508(6) Uani 1 1 d . . . . .
H15A H 0.712865 0.772479 0.919742 0.061 Uiso 1 1 calc R U . . .
H15B H 0.833566 0.686916 0.870799 0.061 Uiso 1 1 calc R U . . .
C16 C 0.5775(3) 0.6213(2) 0.87449(12) 0.0449(5) Uani 1 1 d . . . . .
H16A H 0.635957 0.542197 0.870974 0.054 Uiso 1 1 calc R U . . .
H16B H 0.520951 0.624617 0.924656 0.054 Uiso 1 1 calc R U . . .
C17 C 0.4290(3) 0.57357(18) 0.59563(12) 0.0369(4) Uani 1 1 d . . . . .
C18 C 0.7458(3) 0.7808(2) 0.58829(13) 0.0410(5) Uani 1 1 d . . . . .
C19 C 0.8811(5) 0.6216(3) 0.52547(16) 0.0673(8) Uani 1 1 d . . . . .
H19A H 0.807597 0.644888 0.480329 0.101 Uiso 1 1 calc R U . . .
H19B H 0.886352 0.533500 0.528952 0.101 Uiso 1 1 calc R U . . .
H19C H 0.998258 0.653791 0.520256 0.101 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 C17 1.232(3) . ?
O2 C17 1.318(2) . ?
O3 C18 1.209(3) . ?
O4 C18 1.337(3) . ?
O4 C19 1.427(3) . ?
C1 C6 1.398(3) . ?
C1 C2 1.410(3) . ?
C1 C7 1.511(3) . ?
C2 C3 1.398(3) . ?
C2 C17 1.487(3) . ?
C3 C4 1.392(3) . ?
C4 C5 1.396(3) . ?
C4 C16 1.507(3) . ?
C5 C6 1.377(3) . ?
C7 C8 1.573(4) . ?
C8 C9 1.526(3) . ?
C9 C14 1.398(3) . ?
C9 C10 1.404(3) . ?
C10 C11 1.399(3) . ?
C10 C18 1.486(3) . ?
C11 C12 1.392(3) . ?
C12 C13 1.399(3) . ?
C12 C15 1.508(3) . ?
C13 C14 1.379(4) . ?
C15 C16 1.569(4) . ?

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
C18 O4 C19 115.99(19) . . ?
C6 C1 C2 115.55(19) . . ?
C6 C1 C7 117.65(19) . . ?
C2 C1 C7 125.85(19) . . ?
C3 C2 C1 120.03(17) . . ?
C3 C2 C17 117.47(17) . . ?
C1 C2 C17 122.20(18) . . ?
C4 C3 C2 121.47(18) . . ?
C3 C4 C5 116.28(19) . . ?
C3 C4 C16 121.03(19) . . ?
C5 C4 C16 121.52(19) . . ?
C6 C5 C4 120.70(19) . . ?
C5 C6 C1 122.05(19) . . ?
C1 C7 C8 113.79(18) . . ?
C9 C8 C7 112.30(19) . . ?
C14 C9 C10 116.2(2) . . ?
C14 C9 C8 119.7(2) . . ?
C10 C9 C8 122.2(2) . . ?
C11 C10 C9 120.49(19) . . ?
C11 C10 C18 118.49(18) . . ?
C9 C10 C18 120.9(2) . . ?
C12 C11 C10 121.3(2) . . ?
C11 C12 C13 116.3(2) . . ?
C11 C12 C15 120.6(2) . . ?
C13 C12 C15 122.0(2) . . ?
C14 C13 C12 121.5(2) . . ?
C13 C14 C9 121.2(2) . . ?
C12 C15 C16 113.45(18) . . ?
C4 C16 C15 112.45(18) . . ?
O1 C17 O2 122.36(19) . . ?
O1 C17 C2 124.29(18) . . ?
O2 C17 C2 113.35(18) . . ?
O3 C18 O4 122.6(2) . . ?
O3 C18 C10 125.9(2) . . ?
O4 C18 C10 111.54(18) . . ?

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_ic21559
_database_code_depnum_ccdc_archive 'CCDC 2280497'
loop_
_audit_author_name
_audit_author_address
'Su-Ying Chien'
;Instrumentation Center, National Taiwan University, Taipei, Taiwan
Taiwan
;
_audit_update_record             
;
2023-07-10 deposited with the CCDC.	2023-11-21 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            'C19 H18 O4'
_chemical_formula_weight         310.33

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.8405(4)
_cell_length_b                   10.9929(6)
_cell_length_c                   17.4746(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1506.13(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3972
_cell_measurement_theta_min      4.5810
_cell_measurement_theta_max      77.0600

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.149
_exptl_absorpt_coefficient_mu    0.780
_shelx_estimated_absorpt_T_min   0.808
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_reflns_number            7840
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.752
_diffrn_reflns_theta_max         67.999
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2741
_reflns_number_gt                2362
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1272P)²+0.0460P] 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_abs_structure_details 
; 
 Flack x determined using 812 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.4(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2741
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0674
_refine_ls_wR_factor_ref         0.1917
_refine_ls_wR_factor_gt          0.1791
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.7731(7) 0.5806(5) 0.7332(2) 0.0753(14) Uani 1 1 d . . . . .
O2 O 0.7162(6) 0.7574(3) 0.6772(2) 0.0566(9) Uani 1 1 d . . . . .
H2A H 0.665077 0.769873 0.718713 0.085 Uiso 1 1 calc R U . . .
O3 O 0.4651(6) 0.3487(3) 0.7025(3) 0.0630(11) Uani 1 1 d . . . . .
O4 O 0.4095(5) 0.5396(3) 0.66464(18) 0.0469(8) Uani 1 1 d . . . . .
C1 C 0.9703(6) 0.5116(4) 0.5947(3) 0.0415(9) Uani 1 1 d . . . . .
C2 C 0.8598(6) 0.6110(4) 0.6024(3) 0.0390(9) Uani 1 1 d . . . . .
C3 C 0.8052(6) 0.6736(3) 0.5374(3) 0.0393(9) Uani 1 1 d . . . . .
H3A H 0.730575 0.741033 0.543309 0.047 Uiso 1 1 calc R U . . .
C4 C 0.8565(7) 0.6404(4) 0.4646(3) 0.0432(10) Uani 1 1 d . . . . .
C5 C 0.9957(7) 0.5616(4) 0.4603(3) 0.0472(11) Uani 1 1 d . . . . .
H5A H 1.053656 0.551349 0.412985 0.057 Uiso 1 1 calc R U . . .
C6 C 1.0498(6) 0.4987(4) 0.5239(3) 0.0461(10) Uani 1 1 d . . . . .
H6A H 1.144032 0.444865 0.519370 0.055 Uiso 1 1 calc R U . . .
C7 C 0.9824(7) 0.4068(5) 0.6500(3) 0.0535(12) Uani 1 1 d . . . . .
H7A H 0.984473 0.439338 0.702814 0.064 Uiso 1 1 calc R U . . .
H7B H 1.091322 0.363451 0.641227 0.064 Uiso 1 1 calc R U . . .
C8 C 0.8306(6) 0.3129(5) 0.6428(3) 0.0517(12) Uani 1 1 d . . . . .
H8A H 0.878250 0.230030 0.636737 0.062 Uiso 1 1 calc R U . . .
H8B H 0.763163 0.314176 0.690676 0.062 Uiso 1 1 calc R U . . .
C9 C 0.7128(6) 0.3396(4) 0.5757(3) 0.0398(9) Uani 1 1 d . . . . .
C10 C 0.5699(5) 0.4168(4) 0.5815(3) 0.0372(9) Uani 1 1 d . . . . .
C11 C 0.5185(6) 0.4857(4) 0.5187(2) 0.0382(9) Uani 1 1 d . . . . .
H11A H 0.427593 0.542093 0.524365 0.046 Uiso 1 1 calc R U . . .
C12 C 0.5977(6) 0.4735(4) 0.4475(2) 0.0410(10) Uani 1 1 d . . . . .
C13 C 0.7103(7) 0.3761(4) 0.4385(3) 0.0450(10) Uani 1 1 d . . . . .
H13A H 0.747732 0.353874 0.388722 0.054 Uiso 1 1 calc R U . . .
C14 C 0.7680(6) 0.3118(4) 0.5015(3) 0.0439(10) Uani 1 1 d . . . . .
H14A H 0.846920 0.247256 0.494254 0.053 Uiso 1 1 calc R U . . .
C15 C 0.5901(7) 0.5741(5) 0.3893(3) 0.0547(13) Uani 1 1 d . . . . .
H15A H 0.482173 0.619589 0.395985 0.066 Uiso 1 1 calc R U . . .
H15B H 0.589396 0.538051 0.337391 0.066 Uiso 1 1 calc R U . . .
C16 C 0.7440(9) 0.6654(5) 0.3957(3) 0.0568(14) Uani 1 1 d . . . . .
H16A H 0.813864 0.659921 0.348640 0.068 Uiso 1 1 calc R U . . .
H16B H 0.699044 0.749385 0.399250 0.068 Uiso 1 1 calc R U . . .
C17 C 0.7846(6) 0.6464(5) 0.6779(3) 0.0461(10) Uani 1 1 d . . . . .
C18 C 0.4789(6) 0.4302(4) 0.6557(3) 0.0419(10) Uani 1 1 d . . . . .
C19 C 0.3317(9) 0.5672(5) 0.7376(3) 0.0583(14) Uani 1 1 d . . . . .
H19A H 0.285743 0.650106 0.736502 0.087 Uiso 1 1 calc R U . . .
H19B H 0.239084 0.509479 0.747570 0.087 Uiso 1 1 calc R U . . .
H19C H 0.417501 0.560802 0.778167 0.087 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 C17 1.210(7) . ?
O2 C17 1.333(6) . ?
O3 C18 1.217(6) . ?
O4 C18 1.330(6) . ?
O4 C19 1.445(6) . ?
C1 C6 1.392(7) . ?
C1 C2 1.401(7) . ?
C1 C7 1.507(7) . ?
C2 C3 1.396(6) . ?
C2 C17 1.496(6) . ?
C3 C4 1.383(6) . ?
C4 C5 1.395(7) . ?
C4 C16 1.518(8) . ?
C5 C6 1.376(7) . ?
C7 C8 1.581(8) . ?
C8 C9 1.522(7) . ?
C9 C14 1.400(7) . ?
C9 C10 1.409(6) . ?
C10 C11 1.394(6) . ?
C10 C18 1.487(6) . ?
C11 C12 1.397(6) . ?
C12 C13 1.397(6) . ?
C12 C15 1.504(7) . ?
C13 C14 1.385(7) . ?
C15 C16 1.573(9) . ?

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
C18 O4 C19 117.8(4) . . ?
C6 C1 C2 116.2(4) . . ?
C6 C1 C7 117.6(4) . . ?
C2 C1 C7 125.0(4) . . ?
C3 C2 C1 119.7(4) . . ?
C3 C2 C17 117.9(4) . . ?
C1 C2 C17 122.1(4) . . ?
C4 C3 C2 122.0(4) . . ?
C3 C4 C5 116.2(5) . . ?
C3 C4 C16 120.8(4) . . ?
C5 C4 C16 121.6(4) . . ?
C6 C5 C4 120.6(4) . . ?
C5 C6 C1 121.9(4) . . ?
C1 C7 C8 113.6(4) . . ?
C9 C8 C7 113.1(4) . . ?
C14 C9 C10 116.4(4) . . ?
C14 C9 C8 118.9(4) . . ?
C10 C9 C8 122.9(4) . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 C18 119.7(4) . . ?
C9 C10 C18 120.3(4) . . ?
C10 C11 C12 121.4(4) . . ?
C11 C12 C13 117.0(4) . . ?
C11 C12 C15 121.0(4) . . ?
C13 C12 C15 120.8(4) . . ?
C14 C13 C12 120.6(4) . . ?
C13 C14 C9 121.6(4) . . ?
C12 C15 C16 113.0(4) . . ?
C4 C16 C15 112.7(4) . . ?
O1 C17 O2 121.7(5) . . ?
O1 C17 C2 125.3(5) . . ?
O2 C17 C2 112.8(4) . . ?
O3 C18 O4 123.4(4) . . ?
O3 C18 C10 123.8(4) . . ?
O4 C18 C10 112.8(4) . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_ic21653
_database_code_depnum_ccdc_archive 'CCDC 2280499'
loop_
_audit_author_name
_audit_author_address
'Su-Ying Chien'
;Instrumentation Center, National Taiwan University, Taipei, Taiwan
Taiwan
;
_audit_update_record             
;
2023-07-10 deposited with the CCDC.	2023-11-21 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            'C32 H23 N O4 S'
_chemical_formula_weight         517.57

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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   10.9527(2)
_cell_length_b                   12.7611(3)
_cell_length_c                   17.1116(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2391.66(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14357
_cell_measurement_theta_min      3.3540
_cell_measurement_theta_max      78.2920

_exptl_crystal_description       columnar
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    1.547
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.49552
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_reflns_number            22373
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.322
_diffrn_reflns_theta_max         67.993
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4354
_reflns_number_gt                4226
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1057P)²+0.1736P] 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     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1755 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.024(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4354
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1364
_refine_ls_wR_factor_gt          0.1351
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
S1 S 0.59215(8) 0.87660(6) 0.65198(5) 0.0390(2) Uani 1 1 d . . . . .
O1 O -0.0303(3) 0.5548(2) 0.68404(18) 0.0564(7) Uani 1 1 d . . . . .
O2 O 0.0072(3) 0.7272(2) 0.68092(15) 0.0473(6) Uani 1 1 d . . . . .
O3 O 0.2200(2) 0.78859(18) 0.81868(13) 0.0356(5) Uani 1 1 d . . . . .
O4 O 0.6106(3) 0.5303(2) 0.64303(16) 0.0504(7) Uani 1 1 d . . . . .
N1 N 0.2341(3) 0.6120(2) 0.81523(16) 0.0364(6) Uani 1 1 d . . . . .
C1 C -0.1974(3) 0.5900(3) 0.8137(2) 0.0406(7) Uani 1 1 d . . . . .
C2 C -0.1463(3) 0.6695(3) 0.76743(19) 0.0388(7) Uani 1 1 d . . . . .
C3 C -0.1735(3) 0.7742(3) 0.7831(2) 0.0416(8) Uani 1 1 d . . . . .
H3 H -0.136902 0.826364 0.753303 0.050 Uiso 1 1 calc R U . . .
C4 C -0.2547(3) 0.8024(3) 0.8425(2) 0.0450(8) Uani 1 1 d . . . . .
C5 C -0.3268(3) 0.7220(4) 0.8740(2) 0.0489(9) Uani 1 1 d . . . . .
H5 H -0.394723 0.738480 0.904273 0.059 Uiso 1 1 calc R U . . .
C6 C -0.2970(3) 0.6181(3) 0.8602(2) 0.0459(8) Uani 1 1 d . . . . .
H6 H -0.344659 0.565666 0.882382 0.055 Uiso 1 1 calc R U . . .
C7 C -0.1344(3) 0.4875(3) 0.8304(2) 0.0442(8) Uani 1 1 d . . . . .
H7A H -0.125016 0.448819 0.781976 0.053 Uiso 1 1 calc R U . . .
H7B H -0.185056 0.445994 0.865135 0.053 Uiso 1 1 calc R U . . .
C8 C -0.0041(3) 0.5032(3) 0.8693(2) 0.0444(8) Uani 1 1 d . . . . .
H8A H 0.012961 0.444597 0.903629 0.053 Uiso 1 1 calc R U . . .
H8B H 0.057720 0.504042 0.828675 0.053 Uiso 1 1 calc R U . . .
C9 C 0.0029(3) 0.6043(3) 0.9156(2) 0.0380(7) Uani 1 1 d . . . . .
C10 C 0.0656(3) 0.6959(3) 0.89097(17) 0.0342(7) Uani 1 1 d . . . . .
C11 C 0.0219(3) 0.7952(3) 0.91198(19) 0.0389(7) Uani 1 1 d . . . . .
H11 H 0.061917 0.854643 0.893822 0.047 Uiso 1 1 calc R U . . .
C12 C -0.0807(4) 0.8063(3) 0.9597(2) 0.0441(8) Uani 1 1 d . . . . .
C13 C -0.1196(3) 0.7167(4) 0.9991(2) 0.0471(8) Uani 1 1 d . . . . .
H13 H -0.174287 0.723169 1.040363 0.057 Uiso 1 1 calc R U . . .
C14 C -0.0782(3) 0.6182(3) 0.9776(2) 0.0461(8) Uani 1 1 d . . . . .
H14 H -0.105139 0.559842 1.005284 0.055 Uiso 1 1 calc R U . . .
C15 C -0.1590(4) 0.9032(3) 0.9570(2) 0.0539(10) Uani 1 1 d . . . . .
H15A H -0.106766 0.964505 0.958381 0.065 Uiso 1 1 calc R U . . .
H15B H -0.210658 0.904900 1.003013 0.065 Uiso 1 1 calc R U . . .
C16 C -0.2431(4) 0.9086(3) 0.8808(3) 0.0557(10) Uani 1 1 d . . . . .
H16A H -0.323583 0.933845 0.895136 0.067 Uiso 1 1 calc R U . . .
H16B H -0.208100 0.957779 0.843854 0.067 Uiso 1 1 calc R U . . .
C17 C -0.0519(3) 0.6421(3) 0.70801(19) 0.0387(7) Uani 1 1 d . . . . .
C18 C 0.0997(4) 0.7066(3) 0.6233(2) 0.0491(8) Uani 1 1 d . . . . .
H18A H 0.162324 0.663481 0.645751 0.074 Uiso 1 1 calc R U . . .
H18B H 0.134690 0.771644 0.606080 0.074 Uiso 1 1 calc R U . . .
H18C H 0.063858 0.671020 0.579498 0.074 Uiso 1 1 calc R U . . .
C19 C 0.1731(3) 0.6921(2) 0.83986(18) 0.0331(6) Uani 1 1 d . . . . .
C20 C 0.3306(3) 0.6556(2) 0.77210(18) 0.0328(6) Uani 1 1 d . . . . .
C21 C 0.4232(3) 0.6103(2) 0.72904(19) 0.0353(7) Uani 1 1 d . . . . .
H21 H 0.430757 0.537803 0.725714 0.042 Uiso 1 1 calc R U . . .
C22 C 0.5060(3) 0.6769(3) 0.69027(17) 0.0331(6) Uani 1 1 d . . . . .
C23 C 0.6021(3) 0.6246(3) 0.64331(18) 0.0373(7) Uani 1 1 d . . . . .
C24 C 0.6857(3) 0.6891(3) 0.59460(18) 0.0375(7) Uani 1 1 d . . . . .
C25 C 0.7682(3) 0.6350(3) 0.5458(2) 0.0448(8) Uani 1 1 d . . . . .
H25 H 0.769910 0.562151 0.546206 0.054 Uiso 1 1 calc R U . . .
C26 C 0.8467(4) 0.6899(4) 0.4973(2) 0.0549(11) Uani 1 1 d . . . . .
H26 H 0.899154 0.653976 0.464022 0.066 Uiso 1 1 calc R U . . .
C27 C 0.8468(4) 0.7976(4) 0.4983(2) 0.0532(10) Uani 1 1 d . . . . .
H27 H 0.900145 0.833909 0.465787 0.064 Uiso 1 1 calc R U . . .
C28 C 0.7687(3) 0.8534(3) 0.5471(2) 0.0464(9) Uani 1 1 d . . . . .
H28 H 0.770789 0.926267 0.548291 0.056 Uiso 1 1 calc R U . . .
C29 C 0.6866(3) 0.7977(3) 0.59454(18) 0.0374(7) Uani 1 1 d . . . . .
C30 C 0.4943(3) 0.7862(3) 0.69646(17) 0.0332(6) Uani 1 1 d . . . . .
C31 C 0.4001(3) 0.8330(3) 0.73980(18) 0.0354(6) Uani 1 1 d . . . . .
H31 H 0.391862 0.905350 0.744036 0.042 Uiso 1 1 calc R U . . .
C32 C 0.3212(3) 0.7646(3) 0.77546(17) 0.0320(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C29 1.746(4) . ?
S1 C30 1.749(3) . ?
O1 C17 1.211(5) . ?
O2 C17 1.346(5) . ?
O2 C18 1.439(4) . ?
O3 C32 1.367(4) . ?
O3 C19 1.383(4) . ?
O4 C23 1.208(5) . ?
N1 C19 1.291(4) . ?
N1 C20 1.404(4) . ?
C1 C6 1.396(5) . ?
C1 C2 1.404(5) . ?
C1 C7 1.507(5) . ?
C2 C3 1.395(5) . ?
C2 C17 1.492(5) . ?
C3 C4 1.398(5) . ?
C4 C5 1.402(6) . ?
C4 C16 1.510(6) . ?
C5 C6 1.386(6) . ?
C7 C8 1.587(5) . ?
C8 C9 1.516(5) . ?
C9 C14 1.396(5) . ?
C9 C10 1.419(5) . ?
C10 C11 1.401(5) . ?
C10 C19 1.468(4) . ?
C11 C12 1.397(5) . ?
C12 C13 1.393(6) . ?
C12 C15 1.505(5) . ?
C13 C14 1.387(6) . ?
C15 C16 1.598(6) . ?
C20 C21 1.381(5) . ?
C20 C32 1.396(4) . ?
C21 C22 1.409(5) . ?
C22 C30 1.405(5) . ?
C22 C23 1.483(4) . ?
C23 C24 1.486(5) . ?
C24 C29 1.385(5) . ?
C24 C25 1.411(5) . ?
C25 C26 1.385(6) . ?
C26 C27 1.375(7) . ?
C27 C28 1.391(6) . ?
C28 C29 1.405(5) . ?
C30 C31 1.404(5) . ?
C31 C32 1.372(5) . ?

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
C29 S1 C30 103.14(17) . . ?
C17 O2 C18 115.3(3) . . ?
C32 O3 C19 104.1(2) . . ?
C19 N1 C20 104.4(3) . . ?
C6 C1 C2 116.6(3) . . ?
C6 C1 C7 118.2(3) . . ?
C2 C1 C7 123.5(3) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 C17 120.2(3) . . ?
C1 C2 C17 119.5(3) . . ?
C2 C3 C4 121.5(3) . . ?
C3 C4 C5 116.7(4) . . ?
C3 C4 C16 119.6(4) . . ?
C5 C4 C16 122.5(3) . . ?
C6 C5 C4 120.1(3) . . ?
C5 C6 C1 121.8(4) . . ?
C1 C7 C8 112.4(3) . . ?
C9 C8 C7 111.9(3) . . ?
C14 C9 C10 115.4(3) . . ?
C14 C9 C8 118.2(3) . . ?
C10 C9 C8 124.8(3) . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 C19 117.2(3) . . ?
C9 C10 C19 122.5(3) . . ?
C12 C11 C10 121.1(3) . . ?
C13 C12 C11 116.4(4) . . ?
C13 C12 C15 121.0(4) . . ?
C11 C12 C15 121.6(4) . . ?
C14 C13 C12 121.1(3) . . ?
C13 C14 C9 121.6(3) . . ?
C12 C15 C16 112.9(3) . . ?
C4 C16 C15 111.3(3) . . ?
O1 C17 O2 122.2(3) . . ?
O1 C17 C2 125.6(4) . . ?
O2 C17 C2 112.3(3) . . ?
N1 C19 O3 115.3(3) . . ?
N1 C19 C10 129.5(3) . . ?
O3 C19 C10 115.1(3) . . ?
C21 C20 C32 119.6(3) . . ?
C21 C20 N1 131.9(3) . . ?
C32 C20 N1 108.5(3) . . ?
C20 C21 C22 118.1(3) . . ?
C30 C22 C21 120.3(3) . . ?
C30 C22 C23 123.5(3) . . ?
C21 C22 C23 116.2(3) . . ?
O4 C23 C22 120.3(3) . . ?
O4 C23 C24 120.2(3) . . ?
C22 C23 C24 119.5(3) . . ?
C29 C24 C25 119.0(3) . . ?
C29 C24 C23 123.9(3) . . ?
C25 C24 C23 117.1(3) . . ?
C26 C25 C24 120.3(4) . . ?
C27 C26 C25 119.9(4) . . ?
C26 C27 C28 121.2(4) . . ?
C27 C28 C29 118.8(4) . . ?
C24 C29 C28 120.8(4) . . ?
C24 C29 S1 124.9(3) . . ?
C28 C29 S1 114.3(3) . . ?
C31 C30 C22 122.0(3) . . ?
C31 C30 S1 113.5(3) . . ?
C22 C30 S1 124.5(3) . . ?
C32 C31 C30 115.3(3) . . ?
O3 C32 C31 127.5(3) . . ?
O3 C32 C20 107.8(3) . . ?
C31 C32 C20 124.7(3) . . ?

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.079

