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#$Date: 2024-01-05 14:56:28 +0200 (Fri, 05 Jan 2024) $
#$Revision: 288699 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/97/7159753.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7159753
loop_
_publ_author_name
'Huo, Shou-Chih'
'Indurmuddam, Ranadheer Reddy'
'Hong, Bor-Cherng'
'Lu, Chuan-Fu'
'Chien, Su-Ying'
_publ_section_title
;
 The hamburger-shape photocatalyst: thioxanthone-based chiral
 [2.2]paracyclophane for enantioselective visible-light photocatalysis of
 3-methylquinoxalin-2(1H)-one and styrenes.
;
_journal_issue                   47
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9330
_journal_page_last               9336
_journal_paper_doi               10.1039/d3ob01580g
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C32 H23 N O4 S'
_chemical_formula_weight         517.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-07-10 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9527(2)
_cell_length_b                   12.7611(3)
_cell_length_c                   17.1116(4)
_cell_measurement_reflns_used    14357
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      78.2920
_cell_measurement_theta_min      3.3540
_cell_volume                     2391.66(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.2496
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22373
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.993
_diffrn_reflns_theta_min         4.322
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.547
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49552
_exptl_absorpt_correction_type   multi-scan
_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_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       columnar
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.079
_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)
_refine_ls_extinction_coef       0.0022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4354
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1057P)²+0.1736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1364
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4226
_reflns_number_total             4354
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01580g2.cif
_cod_data_source_block           ic21653
_cod_database_code               7159753
_shelx_shelxl_version_number     2019/1
_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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 . . . . .
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'
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) . . ?
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) . ?
