Acridine photocatalysis enables tricomponent direct decarboxylative amine construction.
Sui, Xianwei; Dang, Hang T.; Porey, Arka; Trevino, Ramon; Das, Arko; Fremin, Seth O.; Hughes, William B.; Thompson, William T.; Dhakal, Shree Krishna; Arman, Hadi D.; Larionov, Oleg V.; Chemical science 15 (2024) 9582–9590; doi:10.1039/d4sc02356k

data_1571695
_publ_section_title
;
 Acridine photocatalysis enables tricomponent direct decarboxylative amine
 construction.
;
_journal_issue                   25
_journal_name_full               'Chemical science'
_journal_page_first              9582
_journal_page_last               9590
_journal_paper_doi               10.1039/d4sc02356k
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C23 H29 N O3'
_chemical_formula_sum            'C23 H29 N O3'
_chemical_formula_weight         367.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-21
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-03-14 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                112.739(2)
_cell_angle_beta                 90.306(2)
_cell_angle_gamma                103.676(2)
_cell_formula_units_Z            4
_cell_length_a                   8.8935(2)
_cell_length_b                   14.9861(4)
_cell_length_c                   16.6162(3)
_cell_measurement_reflns_used    14708
_cell_measurement_temperature    100.01(15)
_cell_measurement_theta_max      76.2220
_cell_measurement_theta_min      2.9160
_cell_volume                     1972.96(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_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    -60.00  26.00   0.50    3.00    --  -46.89  53.00   6.00  172
  2  \w   -119.00 -31.00   0.50    3.00    --  -46.89 -53.00-138.00  176
  3  \w     32.00 119.00   0.50    3.00    --   46.89  53.00   6.00  174
  4  \w   -164.00 -76.00   0.50   12.00    --  -91.75 -53.00-138.00  176
  5  \w    -60.00 -19.00   0.50   12.00    --  -91.75  53.00   6.00   82
  6  \w     34.00  60.00   0.50   12.00    --  106.92 -53.00-138.00   52
  7  \w     92.00 178.00   0.50   12.00    --  106.92  53.00   6.00  172
  8  \w    -85.00 -13.00   0.50    3.00    --  -46.89 125.00-180.00  144
  9  \w     83.00 119.00   0.50    3.00    --   46.89  57.00 -30.00   72
 10  \w    -25.00  60.00   0.50    3.00    --   46.89 -53.00-138.00  170
 11  \w     34.00  94.00   0.50    3.00    --   46.89-125.00-120.00  120
 12  \w    -28.00  30.00   0.50    3.00    --   46.89 -19.00 -90.00  116
 13  \w     83.00 119.00   0.50    3.00    --   46.89  57.00-180.00   72
 14  \w    -51.00 -19.00   0.50   12.00    --  -91.75  45.00 120.00   64
 15  \w   -164.00 -78.00   0.50   12.00    --  -91.75 -56.00 -75.14  172
 16  \w   -101.00 -19.00   0.50   12.00    --  -91.75  77.00-180.00  164
 17  \w   -164.00-101.00   0.50   12.00    --  -91.75 -77.00-180.00  126
 18  \w   -164.00 -83.00   0.50   12.00    --  -91.75 -57.00 -87.57  162
 19  \w   -164.00-101.00   0.50   12.00    --  -91.75 -77.00 -30.00  126
 20  \w    -71.00 -19.00   0.50   12.00    --  -91.75  61.00-180.00  104
 21  \w     34.00 106.00   0.50   12.00    --  106.92 -94.00 150.00  144
 22  \w     34.00  71.00   0.50   12.00    --  106.92 -61.00  90.00   74
 23  \w     34.00 106.00   0.50   12.00    --  106.92 -94.00   0.00  144
 24  \w     34.00 101.00   0.50   12.00    --  106.92 -77.00   0.00  134
 25  \w     34.00  71.00   0.50   12.00    --  106.92 -61.00  30.00   74
 26  \w     37.00 112.00   0.50   12.00    --  106.92-125.00 -90.00  150
 27  \w     37.00 112.00   0.50   12.00    --  106.92-125.00 120.00  150
 28  \w     34.00 106.00   0.50   12.00    --  106.92 -94.00-120.00  144
 29  \w     34.00 106.00   0.50   12.00    --  106.92 -94.00 -60.00  144
 30  \w     34.00  71.00   0.50   12.00    --  106.92 -61.00-150.00   74
 31  \w     92.00 178.00   0.50   12.00    --  106.92  30.00-150.00  172
 32  \w     38.00 109.00   0.50   12.00    --  106.92-116.00   9.29  142
 33  \w    101.00 178.00   0.50   12.00    --  106.92  77.00 -60.00  154
 34  \w     93.00 178.00   0.50   12.00    --  106.92  45.00  90.00  170
 35  \w     37.00 112.00   0.50   12.00    --  106.92-125.00 150.00  150
 36  \w     37.00 112.00   0.50   12.00    --  106.92-125.00   0.00  150
 37  \w     34.00 106.00   0.50   12.00    --  106.92 -94.00-180.00  144
 38  \w     34.00  71.00   0.50   12.00    --  106.92 -61.00   0.00   74
 39  \w   -119.00 -83.00   0.50    3.00    --  -46.89 -57.00 -30.00   72
 40  \w     31.00 119.00   0.50    3.00    --   46.89  55.00-178.70  176
 41  \w     31.00 119.00   0.50    3.00    --   46.89  55.00 102.38  176
;
_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      -0.0830345000
_diffrn_orient_matrix_UB_12      -0.1114223000
_diffrn_orient_matrix_UB_13      -0.0263716000
_diffrn_orient_matrix_UB_21      0.1249626000
_diffrn_orient_matrix_UB_22      -0.0086435000
_diffrn_orient_matrix_UB_23      0.0591676000
_diffrn_orient_matrix_UB_31      -0.0982193000
_diffrn_orient_matrix_UB_32      0.0287201000
_diffrn_orient_matrix_UB_33      0.0776451000
_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  0.0614
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            37064
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.326
_diffrn_reflns_theta_min         2.900
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
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    1.237
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         8018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0783
_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^)+(0.0100P)^2^+5.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1685
_refine_ls_wR_factor_ref         0.1732
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6789
_reflns_number_total             8018
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02356k2.cif
_cod_data_source_block           hpd801b_auto
_cod_depositor_comments
'Adding full bibliography for 1571691--1571695.cif.'
_cod_original_cell_volume        1972.96(8)
_cod_database_code               1571695
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'MCR -11'
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.876
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H11,H1,H2} of C11, All C(H,H) groups
 At 1.5 times of:
  {H23A,H23B,H23C} of C23, {H39A,H39B,H39C} of C39, {H16A,H16B,H16C} of C16,
  {H46A,H46B,H46C} of C46
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C30(H30A,H30B), C27(H27A,H27B), C7(H7A,H7B), C28(H28A,H28B),
 C3(H3A,H3B), C15(H15A,H15B), C38(H38A,H38B), C4(H4A,H4B), C6(H6A,H6B),
 C29(H29A,H29B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C45(H45), C21(H21), C18(H18), C41(H41), C42(H42), C44(H44),
 C36(H36), C19(H19), C32(H32), C9(H9), C13(H13), C35(H35), C33(H33), C34(H34),
 C12(H12), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C16(H16A,H16B,H16C), C46(H46A,H46B,H46C), C23(H23A,H23B,
 H23C)
;
_shelx_res_checksum              23022
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.662
_oxdiff_exptl_absorpt_empirical_full_min 0.428