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_1571694
_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         'C21 H23 N O'
_chemical_formula_sum            'C21 H23 N O'
_chemical_formula_weight         305.40
_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             2023-11-07
_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                90
_cell_angle_beta                 99.380(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.71447(11)
_cell_length_b                   17.9506(3)
_cell_length_c                   16.3618(3)
_cell_measurement_reflns_used    9444
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7690
_cell_measurement_theta_min      3.6670
_cell_volume                     1655.92(5)
_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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.917
_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     34.00 101.00   0.50    1.04    --  106.92 -77.00 -60.00  134
  2  \w     34.00  71.00   0.50    1.04    --  106.92 -61.00 -60.00   74
  3  \w     34.00 101.00   0.50    1.04    --  106.92 -77.00  30.00  134
  4  \w     34.00  71.00   0.50    1.04    --  106.92 -61.00  60.00   74
  5  \w     34.00  71.00   0.50    1.04    --  106.92 -61.00 120.00   74
  6  \w    -26.00  49.00   0.50    0.26    --   46.89 -43.00  59.00  150
  7  \w     32.00  95.00   0.50    0.26    --   46.89  37.00 -60.00  126
  8  \w     92.00 178.00   0.50    1.04    --  106.92  43.00-149.00  172
  9  \w     33.00 120.00   0.50    0.26    --   46.89  43.00-149.00  174
 10  \w    -51.00 -19.00   0.50    1.04    --  -91.75  45.00-180.00   64
 11  \w    -51.00 -19.00   0.50    1.04    --  -91.75  45.00 -60.00   64
 12  \w    -49.00 -18.00   0.50    1.04    --  -91.75  43.00-149.00   62
 13  \w    -49.00  27.00   0.50    0.26    --  -46.89  43.00-149.00  152
 14  \w    -51.00 -19.00   0.50    1.04    --  -91.75  45.00  30.00   64
 15  \w    -71.00 -19.00   0.50    1.04    --  -91.75  61.00  30.00  104
 16  \w    -51.00 -19.00   0.50    1.04    --  -91.75  45.00 150.00   64
 17  \w   -164.00 -76.00   0.50    1.04    --  -91.75 -43.00  59.00  176
 18  \w   -164.00-101.00   0.50    1.04    --  -91.75 -77.00 120.00  126
 19  \w   -164.00-101.00   0.50    1.04    --  -91.75 -77.00 150.00  126
 20  \w   -119.00 -32.00   0.50    0.26    --  -46.89 -43.00  59.00  174
 21  \w   -164.00 -91.00   0.50    1.04    --  -91.75 -61.00   0.00  146
 22  \w   -164.00-101.00   0.50    1.04    --  -91.75 -77.00-180.00  126
 23  \w    -85.00 -13.00   0.50    0.26    --  -46.89 125.00 -90.00  144
;
_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      0.0823881000
_diffrn_orient_matrix_UB_12      0.0765273000
_diffrn_orient_matrix_UB_13      0.0363804000
_diffrn_orient_matrix_UB_21      -0.2434548000
_diffrn_orient_matrix_UB_22      0.0333977000
_diffrn_orient_matrix_UB_23      -0.0358722000
_diffrn_orient_matrix_UB_31      -0.0927028000
_diffrn_orient_matrix_UB_32      -0.0196948000
_diffrn_orient_matrix_UB_33      0.0806554000
_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  0.0386
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15461
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.736
_diffrn_reflns_theta_min         3.682
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.536
_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    1.225
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0450P)^2^+0.6768P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1053
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2778
_reflns_number_total             3206
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02356k2.cif
_cod_data_source_block           hpd805_auto
_cod_depositor_comments
'Adding full bibliography for 1571691--1571695.cif.'
_cod_original_cell_volume        1655.93(6)
_cod_database_code               1571694
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'MCR 3'
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.903
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C21(H21A,H21B), C20(H20A,H20B), C19(H19A,H19B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C11(H11), C14(H14), C13(H13), C5(H5), C15(H15), C12(H12),
 C6(H6), C8(H8), C7(H7)
;
_shelx_res_checksum              98020
_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 1.630
_oxdiff_exptl_absorpt_empirical_full_min 0.639