The hamburger-shape photocatalyst: thioxanthone-based chiral [2.2]paracyclophane for enantioselective visible-light photocatalysis of 3-methylquinoxalin-2(1<i>H</i>)-one and styrenes.
Huo, Shou-Chih; Indurmuddam, Ranadheer Reddy; Hong, Bor-Cherng; Lu, Chuan-Fu; Chien, Su-Ying; Organic & biomolecular chemistry 21 (2023) 9330–9336; doi:10.1039/d3ob01580g

data_7159655
_publ_section_title
;
 The hamburger-shape photocatalyst: thioxanthone-based chiral
 [2.2]paracyclophane for enantioselective visible-light photocatalysis of
 3-methylquinoxalin-2(1<i>H</i>)-one and styrenes.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; 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            'C16 H20 N4 O6'
_chemical_formula_weight         364.36
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc2f1qfn
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-01-13 deposited with the CCDC.	2023-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                74.980(12)
_cell_angle_beta                 85.102(12)
_cell_angle_gamma                79.447(12)
_cell_formula_units_Z            2
_cell_length_a                   4.8265(7)
_cell_length_b                   11.8034(18)
_cell_length_c                   16.146(2)
_cell_measurement_reflns_used    2200
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      73.1660
_cell_measurement_theta_min      4.1900
_cell_volume                     872.7(2)
_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_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.2496
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1226
_diffrn_reflns_av_unetI/netI     0.0977
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10899
_diffrn_reflns_point_group_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.980
_diffrn_reflns_theta_min         3.933
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41539
_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            yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.159
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   0.3(9)
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.376
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     482
_refine_ls_number_reflns         5724
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.379
_refine_ls_R_factor_all          0.1726
_refine_ls_R_factor_gt           0.1206
_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/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2821
_refine_ls_wR_factor_ref         0.3346
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.812
_reflns_Friedel_fraction_max     0.811
_reflns_number_gt                2944
_reflns_number_total             5724
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01580g2.cif
_cod_data_source_block           ic21707
_cod_depositor_comments
;
Adding full bibliography for 7159654--7159657.cif.

2024-09-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C32 H40 N8 O12'
_cod_original_formula_weight         728.72
_cod_original_formula_units_Z            1
_cod_database_code               7159655
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.611
_shelx_estimated_absorpt_t_max   0.869
_shelx_res_checksum              30917
_shelx_hkl_checksum              24873