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_4518062
_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         'C16 H26 O2'
_chemical_formula_sum            'C16 H26 O2'
_chemical_formula_weight         250.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-07
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.4427(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.9880(3)
_cell_length_b                   6.72515(7)
_cell_length_c                   18.4587(2)
_cell_measurement_reflns_used    11723
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.6570
_cell_measurement_theta_min      2.5610
_cell_volume                     2808.00(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-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (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 0.998
_diffrn_measured_fraction_theta_max 0.957
_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    -58.00  26.00   0.50    0.20    --  -46.87  51.00 153.00  168
  2  \w   -120.00 -32.00   0.50    0.20    --  -46.87 -51.00   7.00  176
  3  \w    -25.00  58.00   0.50    0.20    --   46.87 -51.00   7.00  166
  4  \w   -160.00 -72.00   0.50    0.80    --  -88.50 -51.00   7.00  176
  5  \w    -58.00 -15.00   0.50    0.80    --  -88.50  51.00 153.00   86
  6  \w     91.00 178.00   0.50    0.80    --  106.69  51.00 153.00  174
  7  \w   -120.00 -87.00   0.50    0.20    --  -46.87-125.00-180.00   66
  8  \w   -120.00 -87.00   0.50    0.20    --  -46.87-125.00 150.00   66
  9  \w     32.00 120.00   0.50    0.20    --   46.87  51.00 153.00  176
 10  \w    -51.00 -16.00   0.50    0.80    --  -88.50  45.00  90.00   70
 11  \w    -71.00 -15.00   0.50    0.80    --  -88.50  61.00 -60.00  112
 12  \w    -51.00 -16.00   0.50    0.80    --  -88.50  45.00 -60.00   70
 13  \w    -51.00 -16.00   0.50    0.80    --  -88.50  45.00 -30.00   70
 14  \w   -160.00-101.00   0.50    0.80    --  -88.50 -77.00 120.00  118
 15  \w    -51.00 -16.00   0.50    0.80    --  -88.50  45.00   0.00   70
 16  \w    -51.00 -16.00   0.50    0.80    --  -88.50  45.00 120.00   70
 17  \w     34.00 101.00   0.50    0.80    --  106.69 -77.00 -60.00  134
 18  \w     34.00  71.00   0.50    0.80    --  106.69 -61.00 120.00   74
 19  \w     34.00 101.00   0.50    0.80    --  106.69 -77.00  90.00  134
 20  \w     89.00 178.00   0.50    0.80    --  106.69  15.00-120.00  178
 21  \w     95.00 178.00   0.50    0.80    --  106.69 125.00   0.00  166
 22  \w     34.00 101.00   0.50    0.80    --  106.69 -77.00  30.00  134
 23  \w     34.00  71.00   0.50    0.80    --  106.69 -61.00 150.00   74
 24  \w   -120.00 -83.00   0.50    0.20    --  -46.87 -57.00 120.00   74
 25  \w   -121.00 -32.00   0.50    0.20    --  -46.87 -37.00 150.00  178
 26  \w   -121.00 -32.00   0.50    0.20    --  -46.87 -37.00  60.00  178
 27  \w   -121.00 -56.00   0.50    0.20    --  -46.87 -37.00 -90.00  130
 28  \w   -121.00 -32.00   0.50    0.20    --  -46.87 -37.00-120.00  178
;
_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      0.0677552000
_diffrn_orient_matrix_UB_12      -0.0226529000
_diffrn_orient_matrix_UB_13      0.0310134000
_diffrn_orient_matrix_UB_21      -0.0030565000
_diffrn_orient_matrix_UB_22      -0.1408465000
_diffrn_orient_matrix_UB_23      -0.0670951000
_diffrn_orient_matrix_UB_31      0.0061222000
_diffrn_orient_matrix_UB_32      0.1792399000
_diffrn_orient_matrix_UB_33      -0.0487084000
_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  0.0239
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16406
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.424
_diffrn_reflns_theta_min         3.908
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.841
_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    1.184
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0390P)^2^+1.7997P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0883
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2609
_reflns_number_total             2832
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03440_si_003.cif
_cod_data_source_block           hpd062_try2
_cod_depositor_comments
'Adding full bibliography for 4518056--4518062.cif.'
_cod_database_code               4518062
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H20O1
_chemical_oxdiff_usercomment     HDA913-6
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.915
_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,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C8(H8), C5(H5), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C14(H14A,H14B), C7(H7A,H7B), C2(H2A,H2B), C12(H12A,H12B), C9(H9A,
 H9B), C10(H10A,H10B), C15(H15A,H15B), C4(H4A,H4B)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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 1.244
_oxdiff_exptl_absorpt_empirical_full_min 0.806