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_1571692
_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         'C20 H25 N'
_chemical_formula_sum            'C20 H25 N'
_chemical_formula_weight         279.41
_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             2021-02-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2024-03-14 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.2646(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.64642(5)
_cell_length_b                   20.42415(18)
_cell_length_c                   13.59672(11)
_cell_measurement_reflns_used    20513
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3620
_cell_measurement_theta_min      3.8730
_cell_volume                     1566.79(2)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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 1.000
_diffrn_measured_fraction_theta_max 0.988
_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    -75.00  26.00   0.50    0.17    --  -46.75  88.00 -47.00  202
  2  \w    -21.00  76.00   0.50    0.17    --   46.75 -88.00-164.00  194
  3  \w   -117.00 -15.00   0.50    0.66    --  -88.50  88.00 -47.00  204
  4  \w   -160.00 -79.00   0.50    0.66    --  -88.50 -88.00-164.00  162
  5  \w    101.00 178.00   0.50    0.66    --  106.69  88.00 -47.00  154
  6  \w     34.00 135.00   0.50    0.66    --  106.69 -88.00-164.00  202
  7  \w   -121.00 -32.00   0.50    0.17    --  -46.75 -37.00  60.00  178
  8  \w   -119.00 -83.00   0.50    0.17    --  -46.75 -57.00   0.00   72
  9  \w    -70.00  26.00   0.50    0.17    --  -46.75  77.00  60.00  192
 10  \w   -119.00 -83.00   0.50    0.17    --  -46.75 -57.00 -90.00   72
 11  \w   -119.00 -83.00   0.50    0.17    --  -46.75 -57.00 -60.00   72
 12  \w     83.00 119.00   0.50    0.17    --   46.75  57.00 -30.00   72
 13  \w     83.00 119.00   0.50    0.17    --   46.75  57.00 -60.00   72
 14  \w    -29.00  30.00   0.50    0.17    --   46.75 -19.00-180.00  118
 15  \w    -51.00 -16.00   0.50    0.66    --  -88.50  45.00  30.00   70
 16  \w   -160.00-100.00   0.50    0.66    --  -88.50 -94.00-150.00  120
 17  \w   -160.00-100.00   0.50    0.66    --  -88.50 -94.00 150.00  120
 18  \w    -51.00 -16.00   0.50    0.66    --  -88.50  45.00-120.00   70
 19  \w   -160.00-101.00   0.50    0.66    --  -88.50 -77.00-150.00  118
 20  \w    -51.00 -16.00   0.50    0.66    --  -88.50  45.00 150.00   70
 21  \w    -71.00 -15.00   0.50    0.66    --  -88.50  61.00-120.00  112
 22  \w    -51.00 -16.00   0.50    0.66    --  -88.50  45.00 -30.00   70
 23  \w    -51.00 -16.00   0.50    0.66    --  -88.50  45.00  90.00   70
 24  \w   -163.00 -73.00   0.50    0.66    --  -88.50 -30.00  30.00  180
 25  \w     34.00  71.00   0.50    0.66    --  106.69 -61.00-150.00   74
 26  \w     34.00 105.00   0.50    0.66    --  106.69 -94.00 -90.00  142
 27  \w     34.00 101.00   0.50    0.66    --  106.69 -77.00  90.00  134
 28  \w     92.00 178.00   0.50    0.66    --  106.69  45.00   0.00  172
 29  \w     91.00 178.00   0.50    0.66    --  106.69  30.00 -90.00  174
 30  \w     92.00 178.00   0.50    0.66    --  106.69  45.00 -90.00  172
 31  \w     91.00 178.00   0.50    0.66    --  106.69  30.00  60.00  174
 32  \w     91.00 178.00   0.50    0.66    --  106.69  30.00  90.00  174
 33  \w     34.00 101.00   0.50    0.66    --  106.69 -77.00 -30.00  134
 34  \w     34.00 101.00   0.50    0.66    --  106.69 -77.00 150.00  134
 35  \w     34.00 105.00   0.50    0.66    --  106.69 -94.00 150.00  142
 36  \w     34.00 105.00   0.50    0.66    --  106.69 -94.00 120.00  142
 37  \w     34.00 105.00   0.50    0.66    --  106.69 -94.00 -60.00  142
 38  \w     34.00  71.00   0.50    0.66    --  106.69 -61.00  30.00   74
 39  \w   -121.00 -32.00   0.50    0.17    --  -46.75 -37.00 150.00  178
 40  \w     32.00 121.00   0.50    0.17    --   46.75  37.00-150.00  178
 41  \w     32.00 121.00   0.50    0.17    --   46.75  37.00 150.00  178
 42  \w     32.00 121.00   0.50    0.17    --   46.75  37.00  90.00  178
 43  \w     32.00 121.00   0.50    0.17    --   46.75  37.00 -30.00  178
 44  \w     32.00 121.00   0.50    0.17    --   46.75  37.00-120.00  178
 45  \w     32.00 121.00   0.50    0.17    --   46.75  37.00 -60.00  178
 46  \w     32.00 121.00   0.50    0.17    --   46.75  37.00  30.00  178
 47  \w     91.00 130.00   0.50    0.66    --  106.69  30.00 -30.00   78
 48  \w     91.00 178.00   0.50    0.66    --  106.69  30.00-150.00  174
;
_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      -0.0152136000
_diffrn_orient_matrix_UB_12      -0.0185065000
_diffrn_orient_matrix_UB_13      0.1094334000
_diffrn_orient_matrix_UB_21      -0.1180164000
_diffrn_orient_matrix_UB_22      -0.0654718000
_diffrn_orient_matrix_UB_23      -0.0296982000
_diffrn_orient_matrix_UB_31      0.2456949000
_diffrn_orient_matrix_UB_32      -0.0325554000
_diffrn_orient_matrix_UB_33      -0.0025631000
_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  0.0455
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35340
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.664
_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    0.507
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.465
_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    1.185
_exptl_crystal_description       plank
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0017(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   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0472P)^2^+0.7000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3003
_reflns_number_total             3256
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02356k2.cif
_cod_data_source_block           hpd291
_cod_depositor_comments
'Adding full bibliography for 1571691--1571695.cif.'
_cod_database_code               1571692
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     'Sample 123-4'
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.884
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C12(H12), C9(H9), C15(H15), C20(H20), C14(H14), C18(H18), C10(H10),
 C17(H17), C11(H11)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              80747
_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 1.379
_oxdiff_exptl_absorpt_empirical_full_min 0.770