Acridine Photocatalysis: Insights into the Mechanism and Development of a Dual-Catalytic Direct Decarboxylative Conjugate Addition
Dang, Hang T.; Haug, Graham C.; Nguyen, Vu T.; Vuong, Ngan T. H.; Nguyen, Viet D.; Arman, Hadi D.; Larionov, Oleg V.; ACS Catalysis 10 (2020) 11448–11457; doi:10.1021/acscatal.0c03440

data_4518056
_publ_section_title
;
 Acridine Photocatalysis: Insights into the Mechanism and Development of a
 Dual-Catalytic Direct Decarboxylative Conjugate Addition
;
_journal_issue                   19
_journal_name_full               'ACS Catalysis'
_journal_page_first              11448
_journal_page_last               11457
_journal_paper_doi               10.1021/acscatal.0c03440
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C20 H24 O5 S2'
_chemical_formula_sum            'C20 H24 O5 S2'
_chemical_formula_weight         408.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-06-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.16970(10)
_cell_length_b                   8.54580(10)
_cell_length_c                   33.8861(3)
_cell_measurement_reflns_used    12020
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.8520
_cell_measurement_theta_min      2.6040
_cell_volume                     3813.73(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     83.00 120.00   0.50    0.28    --   46.87  57.00 120.00   74
  2  \w     34.00  89.00   0.50    1.14    --  106.69 -72.00 162.00  110
  3  \w     34.00 109.00   0.50    1.14    --  106.69 -79.00  47.00  150
  4  \w     42.00  69.00   0.50    1.14    --  106.69 -61.00  90.00   54
  5  \w     37.00  70.00   0.50    1.14    --  106.69 -61.00 -30.00   66
  6  \w     70.00 108.00   0.50    1.14    --  106.69-125.00-180.00   76
  7  \w     34.00  65.00   0.50    1.14    --  106.69-125.00-180.00   62
  8  \w   -120.00 -83.00   0.50    0.28    --  -46.87 -57.00   0.00   74
  9  \w   -120.00 -83.00   0.50    0.28    --  -46.87 -57.00  60.00   74
 10  \w   -120.00 -83.00   0.50    0.28    --  -46.87 -57.00 120.00   74
 11  \w   -120.00 -87.00   0.50    0.28    --  -46.87-125.00 150.00   66
 12  \w   -120.00 -87.00   0.50    0.28    --  -46.87-125.00 -30.00   66
 13  \w   -160.00 -67.00   0.50    1.14    --  -88.50 -70.00 -73.00  186
 14  \w    -51.00 -26.00   0.50    1.14    --  -88.50  45.00 -90.00   50
 15  \w    -65.00 -19.00   0.50    1.14    --  -88.50  61.00 -90.00   92
 16  \w    -89.00 -15.00   0.50    1.14    --  -88.50  72.00 -67.00  148
 17  \w    107.00 150.00   0.50    1.14    --  106.69 125.00-150.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0638436000
_diffrn_orient_matrix_UB_12      -0.1413680000
_diffrn_orient_matrix_UB_13      0.0134087000
_diffrn_orient_matrix_UB_21      0.0693371000
_diffrn_orient_matrix_UB_22      0.0201697000
_diffrn_orient_matrix_UB_23      -0.0362848000
_diffrn_orient_matrix_UB_31      0.0693021000
_diffrn_orient_matrix_UB_32      0.1100582000
_diffrn_orient_matrix_UB_33      0.0238679000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            19244
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.389
_diffrn_reflns_theta_min         2.608
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.784
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       plate
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.00020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0282P)^2^+2.8094P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0767
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3474
_reflns_number_total             3799
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03440_si_002.cif
_cod_data_source_block           hpd118
_cod_depositor_comments
'Adding full bibliography for 4518056--4518062.cif.'
_cod_database_code               4518056
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O S'
_chemical_oxdiff_usercomment     HO223-3
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B), C19(H19A,H19B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C9(H9), C11(H11), C3(H3), C7(H7), C10(H10), C12(H12), C4(H4),
 C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              41152
_shelx_hkl_checksum              87780
_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.219
_oxdiff_exptl_absorpt_empirical_full_min 0.853