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_4518058
_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         'C15 H20 O2'
_chemical_formula_sum            'C15 H20 O2'
_chemical_formula_weight         232.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-17
_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                 93.8866(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.46515(12)
_cell_length_b                   7.56208(15)
_cell_length_c                   26.4823(6)
_cell_measurement_reflns_used    6622
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.7200
_cell_measurement_theta_min      3.3500
_cell_volume                     1291.74(5)
_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 0.999
_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     31.00 120.00   0.50    0.14    --   46.87  55.00 -42.00  178
  2  \w     91.00 178.00   0.50    0.56    --  106.69  55.00 -42.00  174
  3  \w     95.00 178.00   0.50    0.56    --  106.69 125.00-150.00  166
  4  \w     91.00 178.00   0.50    0.56    --  106.69  61.00  30.00  174
  5  \w     34.00  63.00   0.50    0.56    --  106.69 -55.00 174.00   58
  6  \w    -25.00  63.00   0.50    0.14    --   46.87 -55.00 174.00  176
  7  \w     34.00  71.00   0.50    0.56    --  106.69 -61.00 -30.00   74
  8  \w     34.00 111.00   0.50    0.56    --  106.69-125.00-180.00  154
  9  \w     34.00 101.00   0.50    0.56    --  106.69 -77.00-180.00  134
 10  \w    -62.00  26.00   0.50    0.14    --  -46.87  55.00 -42.00  176
 11  \w    -51.00 -16.00   0.50    0.56    --  -88.50  45.00-180.00   70
 12  \w    -51.00 -16.00   0.50    0.56    --  -88.50  45.00 -90.00   70
 13  \w    -63.00 -15.00   0.50    0.56    --  -88.50  55.00 -42.00   96
 14  \w    -51.00 -16.00   0.50    0.56    --  -88.50  45.00  60.00   70
 15  \w    -51.00 -16.00   0.50    0.56    --  -88.50  45.00  90.00   70
 16  \w    -51.00 -16.00   0.50    0.56    --  -88.50  45.00 150.00   70
 17  \w    -51.00 -16.00   0.50    0.56    --  -88.50  45.00 120.00   70
 18  \w   -120.00 -31.00   0.50    0.14    --  -46.87 -55.00 174.00  178
 19  \w   -120.00 -87.00   0.50    0.14    --  -46.87-125.00  30.00   66
 20  \w   -120.00 -87.00   0.50    0.14    --  -46.87-125.00 -60.00   66
 21  \w   -121.00 -92.00   0.50    0.14    --  -46.87 -37.00  60.00   58
 22  \w   -160.00 -73.00   0.50    0.56    --  -88.50 -55.00 174.00  174
 23  \w   -160.00-101.00   0.50    0.56    --  -88.50 -77.00  90.00  118
 24  \w   -160.00-101.00   0.50    0.56    --  -88.50 -77.00 -60.00  118
;
_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      0.0194594000
_diffrn_orient_matrix_UB_12      0.0557930000
_diffrn_orient_matrix_UB_13      0.0560637000
_diffrn_orient_matrix_UB_21      0.1818874000
_diffrn_orient_matrix_UB_22      0.1231713000
_diffrn_orient_matrix_UB_23      -0.0107869000
_diffrn_orient_matrix_UB_31      -0.1536148000
_diffrn_orient_matrix_UB_32      0.1523709000
_diffrn_orient_matrix_UB_33      -0.0118059000
_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  0.0379
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12463
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.536
_diffrn_reflns_theta_min         3.345
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.683
_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    1.195
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.109
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0291P)^2^+0.7448P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0963
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2293
_reflns_number_total             2575
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03440_si_007.cif
_cod_data_source_block           hpd120
_cod_depositor_comments
'Adding full bibliography for 4518056--4518062.cif.'
_cod_original_cell_volume        1291.74(4)
_cod_database_code               4518058
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_chemical_oxdiff_usercomment     'HDA 834-3'
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.936
_reflns_odcompleteness_completeness 99.96
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C13(H13A,H13B), C5(H5A,H5B), C14(H14A,H14B), C3(H3A,
 H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8), C11(H11), C10(H10), C9(H9)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 1.172
_oxdiff_exptl_absorpt_empirical_full_min 0.833