Photocatalytic C-H amination of electron-rich arenes by novel fused quinoline-based photocatalysts.
Shu, Qian; Li, Dinghao; Zheng, Siyu; Lu, Xue-Lian; Sun, Bing; Zhang, Fang-Lin; Organic & biomolecular chemistry  (2026) –; doi:10.1039/d6ob00270f

data_7161095
_publ_section_title
;
 Photocatalytic C-H amination of electron-rich arenes by novel fused
 quinoline-based photocatalysts.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3318
_journal_page_last               3322
_journal_paper_doi               10.1039/d6ob00270f
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C27 H19 N O'
_chemical_formula_sum            'C27 H19 N O'
_chemical_formula_weight         373.43
_chemical_name_systematic        yzl
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2026-02-14 deposited with the CCDC.	2026-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.736(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6548(6)
_cell_length_b                   18.6047(8)
_cell_length_c                   8.5036(4)
_cell_measurement_reflns_used    4190
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.5150
_cell_measurement_theta_min      4.0530
_cell_volume                     2129.17(17)
_computing_cell_refinement       'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.49a (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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_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    -43.00  27.00   0.50    0.24    --   39.95 -19.00   0.00  140
  2  \w    106.00 167.00   0.50    0.97    --  108.87 102.00  75.00  122
  3  \w     95.00 172.00   0.50    0.97    --  108.87 125.00  30.00  154
  4  \w    -34.00  16.00   0.50    0.24    --   39.95 -19.00-150.00  100
  5  \w     37.00  64.00   0.50    0.97    --  108.87 -61.00  90.00   54
  6  \w     36.00  67.00   0.50    0.97    --  108.87 -61.00 120.00   62
  7  \w     40.00  66.00   0.50    0.97    --  108.87 -61.00  60.00   52
  8  \w     39.00  64.00   0.50    0.97    --  108.87 -61.00   0.00   50
  9  \w     39.00  65.00   0.50    0.97    --  108.87 -61.00-150.00   52
 10  \w     34.00  71.00   0.50    0.97    --  108.87 -61.00-180.00   74
 11  \w     36.00  66.00   0.50    0.97    --  108.87 -61.00 -30.00   60
 12  \w     30.00  55.00   0.50    0.97    --  108.87 -94.00  30.00   50
 13  \w     35.00 100.00   0.50    0.97    --  108.87-125.00  90.00  130
 14  \w     60.00 101.00   0.50    0.97    --  108.87 -94.00  30.00   82
 15  \w     65.00 102.00   0.50    0.97    --  108.87-102.00 -27.00   74
 16  \w     28.00  86.00   0.50    0.24    --   39.95-102.00 -27.00  116
 17  \w    -27.00  43.00   0.50    0.24    --  -39.95  19.00-180.00  140
 18  \w      4.00  41.00   0.50    0.24    --  -39.95  37.00 -60.00   74
 19  \w    -42.00  -1.00   0.50    0.24    --  -39.95  37.00 -60.00   82
 20  \w    -62.00 -36.00   0.50    0.97    --  -94.50  61.00-150.00   52
 21  \w    -70.00 -19.00   0.50    0.97    --  -94.50  61.00-180.00  102
 22  \w    -50.00 -22.00   0.50    0.97    --  -94.50  45.00-180.00   56
 23  \w    -51.00 -17.00   0.50    0.97    --  -94.50  45.00-120.00   68
 24  \w    -47.00 -15.00   0.50    0.97    --  -94.50  45.00 -90.00   64
 25  \w    -51.00 -19.00   0.50    0.97    --  -94.50  45.00 -60.00   64
 26  \w    -49.00 -15.00   0.50    0.97    --  -94.50  45.00  30.00   68
 27  \w    -51.00 -25.00   0.50    0.97    --  -94.50  45.00  60.00   52
 28  \w    -44.00 -13.00   0.50    0.24    --  -39.95 102.00  75.00   62
 29  \w    -72.00 -46.00   0.50    0.97    --  -94.50 102.00  75.00   52
 30  \w   -130.00 -86.00   0.50    0.97    --  -94.50-102.00 -27.00   88
;
_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      0.0228670000
_diffrn_orient_matrix_UB_12      -0.0736287000
_diffrn_orient_matrix_UB_13      -0.0684111000
_diffrn_orient_matrix_UB_21      -0.0996094000
_diffrn_orient_matrix_UB_22      -0.0293661000
_diffrn_orient_matrix_UB_23      0.0349403000
_diffrn_orient_matrix_UB_31      -0.0515170000
_diffrn_orient_matrix_UB_32      0.0240063000
_diffrn_orient_matrix_UB_33      -0.1669886000
_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  0.1280
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4805
_diffrn_reflns_point_group_measured_fraction_full 0.579
_diffrn_reflns_point_group_measured_fraction_max 0.579
_diffrn_reflns_theta_full        63.637
_diffrn_reflns_theta_max         63.637
_diffrn_reflns_theta_min         4.054
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.49a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_preparation       293
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.0(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.261
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2031
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.260
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.1031
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2696
_refine_ls_wR_factor_ref         0.2856
_reflns_Friedel_coverage         0.202
_reflns_Friedel_fraction_full    0.196
_reflns_Friedel_fraction_max     0.196
_reflns_number_gt                1804
_reflns_number_total             2031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00270f2.cif
_cod_data_source_block           yzl-3-20
_cod_depositor_comments          'Adding full bibliography for 7161095.cif.'
_cod_database_code               7161095
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N'
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.937
_reflns_odcompleteness_completeness 96.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C006-C009
 1.47 with sigma of 0.01
 C00E-C00A
 1.47 with sigma of 0.01
 C008-C00X
 1.49 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C005) = Uanis(C006) = Uanis(C00G) = Uanis(C00W) = Uanis(C00O) =
Uanis(C00M)
4. Rigid body (RIGU) restrains
 C008, C00X
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Fixed X: N002(-0.45635)
 Fixed Y: N002(-0.59967)
 Fixed Z: N002(-0.62024)
6.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00F(H00F), C00H(H00H), C00R(H00R), C00G(H00G), C00C(H00C),
 C00V(H00V), C00P(H00P), C00O(H00O), C00W(H00W), C00I(H00I), C00J(H00J),
 C00L(H00L)
6.b Fitted hexagon refined as free rotating group:
 C00F(C008,C00H,C00D,C00T,C00R)
6.c Idealised Me refined as rotating group:
 C00X(H00A,H00D,H00E), C00Y(H00K,H00M,H00N)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              88220
_shelx_fab_checksum              10053
_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 7.544
_oxdiff_exptl_absorpt_empirical_full_min 0.115