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_1571691
_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         'C18 H21 N O'
_chemical_formula_sum            'C18 H21 N O'
_chemical_formula_weight         267.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.75307(9)
_cell_length_b                   16.23315(13)
_cell_length_c                   18.76027(18)
_cell_measurement_reflns_used    11784
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.8720
_cell_measurement_theta_min      3.5980
_cell_volume                     2970.18(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 (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 0.998
_diffrn_measured_fraction_theta_max 0.966
_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   -164.00 -74.00   0.50    0.34    --  -88.50 -26.00 -99.00  180
  2  \w    -82.00 -15.00   0.50    0.34    --  -88.50 109.00 160.00  134
  3  \w    105.00 178.00   0.50    0.34    --  106.69 106.00-104.00  146
  4  \w    -34.00  29.00   0.50    0.09    --  -46.75  26.00  64.00  126
  5  \w   -119.00 -88.00   0.50    0.09    --  -46.75-125.00-180.00   62
  6  \w   -119.00 -88.00   0.50    0.09    --  -46.75-125.00  30.00   62
  7  \w   -119.00 -83.00   0.50    0.09    --  -46.75 -57.00 -30.00   72
  8  \w    -30.00  29.00   0.50    0.09    --  -46.75  19.00-150.00  118
  9  \w    -51.00 -16.00   0.50    0.34    --  -88.50  45.00 -60.00   70
 10  \w    -51.00 -16.00   0.50    0.34    --  -88.50  45.00  60.00   70
 11  \w     34.00  71.00   0.50    0.34    --  106.69 -61.00   0.00   74
 12  \w     34.00 111.00   0.50    0.34    --  106.69-125.00 150.00  154
 13  \w     34.00  71.00   0.50    0.34    --  106.69 -61.00  30.00   74
 14  \w     34.00 105.00   0.50    0.34    --  106.69 -94.00  90.00  142
 15  \w     34.00  71.00   0.50    0.34    --  106.69 -61.00  60.00   74
 16  \w     34.00  71.00   0.50    0.34    --  106.69 -61.00 -30.00   74
 17  \w   -119.00 -94.00   0.50    0.09    --  -46.75 -57.00  60.00   50
 18  \w   -121.00 -32.00   0.50    0.09    --  -46.75 -37.00  90.00  178
;
_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      0.1375237000
_diffrn_orient_matrix_UB_12      -0.0302686000
_diffrn_orient_matrix_UB_13      0.0305408000
_diffrn_orient_matrix_UB_21      0.0666532000
_diffrn_orient_matrix_UB_22      0.0096482000
_diffrn_orient_matrix_UB_23      -0.0740077000
_diffrn_orient_matrix_UB_31      0.0394839000
_diffrn_orient_matrix_UB_32      0.0894914000
_diffrn_orient_matrix_UB_33      0.0182925000
_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  0.0306
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18036
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.115
_diffrn_reflns_theta_min         4.714
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.568
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.547
_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    1.196
_exptl_crystal_description       plank
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00061(9)
_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   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+1.0061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2725
_reflns_number_total             3000
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02356k2.cif
_cod_data_source_block           hpd289
_cod_depositor_comments
'Adding full bibliography for 1571691--1571695.cif.'
_cod_database_code               1571691
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     129-7
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.889
_reflns_odcompleteness_completeness 99.97
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C3(H3A,H3B), C5(H5A,H5B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C12(H12), C10(H10), C18(H18), C14(H14), C11(H11), C17(H17),
 C15(H15), C16(H16)
;
_shelx_res_checksum              43475
_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 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.868