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_4518059
_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 H30 B N O4'
_chemical_formula_sum            'C20 H30 B N O4'
_chemical_formula_weight         359.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.160(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4325(4)
_cell_length_b                   9.9472(3)
_cell_length_c                   15.5089(5)
_cell_measurement_reflns_used    12554
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      28.0200
_cell_measurement_theta_min      2.4190
_cell_volume                     2033.05(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -96.00  17.00   1.00   58.00    --   -7.50 -38.00  30.00  113
  2  \w    -37.00  81.00   1.00   58.00    --   -7.50  57.00-180.00  118
  3  \w    -32.00  81.00   1.00   58.00    --   -7.50  38.00 -90.00  113
  4  \w    -46.00  81.00   1.00   58.00    --   -7.50  19.00  30.00  127
  5  \w    -96.00  25.00   1.00   58.00    --   -7.50 -72.00-120.00  121
  6  \w    -37.00  81.00   1.00   58.00    --   -7.50  57.00  30.00  118
  7  \w    -37.00  11.00   1.00   58.00    --   -7.50  57.00 -30.00   48
  8  \w    -32.00  81.00   1.00   58.00    --   -7.50  38.00 120.00  113
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0531995000
_diffrn_orient_matrix_UB_12      0.0090356000
_diffrn_orient_matrix_UB_13      -0.0128658000
_diffrn_orient_matrix_UB_21      0.0082519000
_diffrn_orient_matrix_UB_22      0.0575194000
_diffrn_orient_matrix_UB_23      -0.0246955000
_diffrn_orient_matrix_UB_31      -0.0001493000
_diffrn_orient_matrix_UB_32      -0.0411516000
_diffrn_orient_matrix_UB_33      -0.0373801000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            50780
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.446
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
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    1.174
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0578
_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^)+(0.0273P)^2^+1.7500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1092
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3580
_reflns_number_total             4006
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03440_si_008.cif
_cod_data_source_block           cd1937b
_cod_depositor_comments
'Adding full bibliography for 4518056--4518062.cif.'
_cod_database_code               4518059
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         B2O2N2C20H20
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.984
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C15(H15A,H15B), C14(H14A,H14B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C4(H4), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C12(H12A,H12B,H12C), C20(H20A,H20B,H20C), C10(H10A,H10B,
 H10C), C11(H11A,H11B,H11C)
;
_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 1.054
_oxdiff_exptl_absorpt_empirical_full_min 0.928