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_4518061
_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_absolute_configuration ad
_chemical_formula_moiety         'C37 H56 O3 S'
_chemical_formula_sum            'C37 H56 O3 S'
_chemical_formula_weight         580.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.7103(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.75517(10)
_cell_length_b                   11.91670(8)
_cell_length_c                   18.31913(11)
_cell_measurement_reflns_used    37143
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.0710
_cell_measurement_theta_min      2.4250
_cell_volume                     3214.35(4)
_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  (Sheldrick, 2015)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.974
_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    -37.00  28.00   0.50    0.45    --  -46.87  30.00 -50.00  130
  2  \w    -43.00  27.00   0.50    0.45    --  -46.87  37.00   0.00  140
  3  \w    -51.00 -16.00   0.50    1.78    --  -88.50  45.00  90.00   70
  4  \w    -51.00 -17.00   0.50    1.78    --  -88.50  45.00  60.00   68
  5  \w    -68.00 -16.00   0.50    1.78    --  -88.50  61.00 120.00  104
  6  \w    -98.00 -72.00   0.50    1.78    --  -88.50 -54.00 -11.44   52
  7  \w   -101.00 -75.00   0.50    1.78    --  -88.50 -52.00  34.85   52
  8  \w    -99.00 -73.00   0.50    1.78    --  -88.50 -53.00   9.50   52
  9  \w   -101.00 -75.00   0.50    1.78    --  -88.50 -52.00 -23.99   52
 10  \w   -103.00 -74.00   0.50    1.78    --  -88.50 -53.00 -17.12   58
 11  \w    -99.00 -73.00   0.50    1.78    --  -88.50 -55.00  27.06   52
 12  \w    -97.00 -72.00   0.50    1.78    --  -88.50 -54.00  55.29   50
 13  \w    -99.00 -73.00   0.50    1.78    --  -88.50 -54.00  20.42   52
 14  \w    -98.00 -73.00   0.50    1.78    --  -88.50 -53.00  66.60   50
 15  \w    -98.00 -72.00   0.50    1.78    --  -88.50 -54.00  82.93   52
 16  \w    -98.00 -72.00   0.50    1.78    --  -88.50 -51.00  32.96   52
 17  \w    -98.00 -72.00   0.50    1.78    --  -88.50 -54.00  31.99   52
 18  \w   -100.00 -74.00   0.50    1.78    --  -88.50 -54.00  50.41   52
 19  \w   -101.00 -75.00   0.50    1.78    --  -88.50 -53.00  -4.12   52
 20  \w   -104.00 -73.00   0.50    1.78    --  -88.50 -55.00 -32.75   62
 21  \w   -113.00 -72.00   0.50    1.78    --  -88.50 -51.00  50.99   82
 22  \w   -116.00 -73.00   0.50    1.78    --  -88.50 -50.00  64.41   86
 23  \w   -112.00 -73.00   0.50    1.78    --  -88.50 -54.00  89.36   78
 24  \w   -121.00 -32.00   0.50    0.45    --  -46.87 -30.00 148.00  178
 25  \w     33.00 122.00   0.50    0.45    --   46.87  30.00 -50.00  178
 26  \w     91.00 178.00   0.50    1.78    --  106.69  30.00 -50.00  174
 27  \w    131.00 175.00   0.50    1.78    --  106.69  45.00 -30.00   88
 28  \w     92.00 123.00   0.50    1.78    --  106.69  45.00  60.00   62
 29  \w     94.00 175.00   0.50    1.78    --  106.69  61.00  30.00  162
 30  \w     92.00 125.00   0.50    1.78    --  106.69  45.00 -30.00   66
 31  \w     95.00 178.00   0.50    1.78    --  106.69  45.00  11.73  166
 32  \w     91.00 162.00   0.50    1.78    --  106.69  61.00  60.00  142
 33  \w     76.00 101.00   0.50    1.78    --  106.69 -77.00-120.00   50
 34  \w     35.00  70.00   0.50    1.78    --  106.69 -61.00-120.00   70
 35  \w     40.00  66.00   0.50    1.78    --  106.69 -77.00-120.00   52
 36  \w     35.00  99.00   0.50    1.78    --  106.69 -77.00-180.00  128
 37  \w     34.00  69.00   0.50    1.78    --  106.69 -61.00 -90.00   70
 38  \w     40.00  66.00   0.50    1.78    --  106.69 -61.00 -30.00   52
 39  \w     36.00 100.00   0.50    1.78    --  106.69 -77.00  30.00  128
 40  \w     41.00  67.00   0.50    1.78    --  106.69 -61.00  30.00   52
 41  \w     34.00  62.00   0.50    1.78    --  106.69 -61.00   0.00   56
 42  \w     34.00  96.00   0.50    1.78    --  106.69-125.00  30.00  124
 43  \w     34.00  70.00   0.50    1.78    --  106.69 -61.00 120.00   72
 44  \w     35.00  63.00   0.50    1.78    --  106.69 -61.00 150.00   56
 45  \w     32.00 121.00   0.50    0.45    --   46.87  37.00  30.00  178
 46  \w     31.00 120.00   0.50    0.45    --   46.87  55.00  48.54  178
 47  \w     32.00 120.00   0.50    0.45    --   46.87  54.00  89.32  176
 48  \w     31.00 120.00   0.50    0.45    --   46.87  55.00 128.09  178
 49  \w     31.00 120.00   0.50    0.45    --   46.87  55.00 111.40  178
 50  \w     34.00  59.00   0.50    1.78    --  106.69 -61.00-150.00   50
 51  \w     34.00  66.00   0.50    1.78    --  106.69 -61.00-180.00   64
 52  \w    -28.00  37.00   0.50    0.45    --   46.87 -30.00 148.00  130
 53  \w   -120.00 -83.00   0.50    0.45    --  -46.87 -57.00-150.00   74
 54  \w   -120.00 -87.00   0.50    0.45    --  -46.87-125.00 -60.00   66
 55  \w   -139.00-113.00   0.50    1.78    --  -88.50 -54.00  31.99   52
 56  \w   -140.00 -74.00   0.50    1.78    --  -88.50 -52.00  60.14  132
 57  \w   -149.00-123.00   0.50    1.78    --  -88.50 -54.00  50.41   52
 58  \w   -160.00 -73.00   0.50    1.78    --  -88.50 -55.00  30.14  174
 59  \w   -156.00-131.00   0.50    1.78    --  -88.50 -50.00  64.41   50
 60  \w   -160.00 -73.00   0.50    1.78    --  -88.50 -52.00  73.58  174
 61  \w   -163.00 -73.00   0.50    1.78    --  -88.50 -30.00 148.00  180
 62  \w   -160.00-123.50   0.50    1.78    --  -88.50 -54.00 -28.17   73
;
_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      -0.1005613000
_diffrn_orient_matrix_UB_12      -0.0332458000
_diffrn_orient_matrix_UB_13      -0.0139513000
_diffrn_orient_matrix_UB_21      0.0187638000
_diffrn_orient_matrix_UB_22      -0.0379058000
_diffrn_orient_matrix_UB_23      -0.0780187000
_diffrn_orient_matrix_UB_31      0.0220604000
_diffrn_orient_matrix_UB_32      -0.1189896000
_diffrn_orient_matrix_UB_33      0.0286823000
_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  0.0415
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            66189
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.626
_diffrn_reflns_theta_min         2.417
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.150
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.551
_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    1.200
_exptl_crystal_description       plate
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.039
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 5318 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     755
_refine_ls_number_reflns         12679
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0529P)^2^+0.4511P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0859
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.895
_reflns_number_gt                12165
_reflns_number_total             12679
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03440_si_005.cif
_cod_data_source_block           hpd153
_cod_depositor_comments
'Adding full bibliography for 4518056--4518062.cif.'
_cod_database_code               4518061
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N S O'
_chemical_oxdiff_usercomment     HD6205-6
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.791
_reflns_odcompleteness_completeness 100.00
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C51(H51), C47(H47), C45(H45), C8(H8), C10(H10), C18(H18), C55(H55)
2.b Secondary CH2 refined with riding coordinates:
 C48(H48A,H48B), C49(H49A,H49B), C19(H19A,H19B), C23(H23A,H23B), C22(H22A,
 H22B), C3(H3A,H3B), C21(H21A,H21B), C44(H44A,H44B), C39(H39A,H39B), C60(H60A,
 H60B), C12(H12A,H12B), C7(H7A,H7B), C11(H11A,H11B), C52(H52A,H52B), C40(H40A,
 H40B), C59(H59A,H59B), C56(H56A,H56B), C43(H43A,H43B), C58(H58A,H58B),
 C15(H15A,H15B), C6(H6A,H6B), C2(H2A,H2B), C24(H24A,H24B), C61(H61A,H61B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C53(H53), C63(H63), C30(H30), C28(H28), C26(H26), C27(H27),
 C67(H67), C64(H64), C29(H29), C66(H66), C65(H65)
2.d Idealised Me refined as rotating group:
 C69(H69A,H69B,H69C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C68(H68A,H68B,
 H68C), C32(H32A,H32B,H32C), C72(H72A,H72B,H72C), C70(H70A,H70B,H70C), C36(H36A,
 H36B,H36C), C37(H37A,H37B,H37C), C71(H71A,H71B,H71C), C35(H35A,H35B,H35C),
 C34(H34A,H34B,H34C), C73(H73A,H73B,H73C), C74(H74A,H74B,H74C)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O3(H3)
;
_shelx_res_checksum              37752
_shelx_hkl_checksum              29471
_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 1.377
_oxdiff_exptl_absorpt_empirical_full_min 0.739