Harnessing visible-light energy for unbiased organic photoelectrocatalysis: synthesis of N-bearing fused rings
Gong, Ming; Huang, Mengmeng; Li, Yabo; Zhang, Jianye; Kim, Jung Keun; Kim, Jong Seung; Wu, Yangjie; Green Chemistry 24 (2022) 837–845; doi:10.1039/D1GC03587H

data_7244047
_publ_section_title
;
 Harnessing visible-light energy for unbiased organic
 photoelectrocatalysis: synthesis of N-bearing fused rings
;
_journal_issue                   2
_journal_name_full               'Green Chemistry'
_journal_page_first              837
_journal_page_last               845
_journal_paper_doi               10.1039/D1GC03587H
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C19 H15 N3 O'
_chemical_formula_sum            'C19 H15 N3 O'
_chemical_formula_weight         301.34
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-14 deposited with the CCDC.	2021-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                81.704(6)
_cell_angle_beta                 86.697(7)
_cell_angle_gamma                83.076(6)
_cell_formula_units_Z            2
_cell_length_a                   7.5372(7)
_cell_length_b                   7.8330(5)
_cell_length_c                   13.1572(11)
_cell_measurement_reflns_used    1651
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2770
_cell_measurement_theta_min      5.7350
_cell_volume                     762.41(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -52.00  35.00   1.00    1.00    --  -33.50  57.00  30.00   87
  2  \w    -71.00  39.00   1.00    1.00    --  -33.50  19.00 -30.00  110
  3  \w     57.00 110.00   1.00    1.00    --   36.47 178.00 -60.00   53
  4  \w     24.00  98.00   1.00    1.00    --   36.47-135.00  -0.00   74
  5  \w      8.00 106.00   1.00    1.00    --   36.47  77.00 150.00   98
  6  \w     57.00 110.00   1.00    1.00    --   36.47 178.00-180.00   53
  7  \w     57.00 110.00   1.00    1.00    --   36.47 178.00  30.00   53
  8  \w     18.00 105.00   1.00    1.00    --   36.47  57.00-180.00   87
  9  \w     57.00 110.00   1.00    1.00    --   36.47 178.00 150.00   53
 10  \w     57.00 110.00   1.00    1.00    --   36.47 178.00  90.00   53
 11  \w    -32.00  55.00   1.00    1.00    --   36.47 -57.00  90.00   87
 12  \w     38.00 124.00   1.00    1.00    --  108.00-134.00 178.00   86
 13  \w    104.00 178.00   1.00    1.00    --  108.00 111.00  30.00   74
 14  \w     79.00 108.00   1.00    1.00    --  108.00-111.00 -30.00   29
 15  \w     38.00  63.00   1.00    1.00    --  108.00-111.00 -30.00   25
 16  \w     50.00 119.00   1.00    1.00    --  108.00 -61.00  90.00   69
 17  \w     91.00 136.00   1.00    1.00    --  108.00 -77.00 -30.00   45
 18  \w    141.00 173.00   1.00    1.00    --  108.00  45.00 120.00   32
 19  \w     93.00 127.00   1.00    1.00    --  108.00  45.00 120.00   34
 20  \w    109.00 135.00   1.00    1.00    --  108.00 -15.00 150.00   26
 21  \w     40.00  75.00   1.00    1.00    --  108.00 -15.00 150.00   35
 22  \w     90.00 115.00   1.00    1.00    --  108.00  45.00-150.00   25
 23  \w    139.00 172.00   1.00    1.00    --  108.00  45.00-150.00   33
 24  \w     44.00 121.00   1.00    1.00    --  108.00 -45.00 -60.00   77
 25  \w     89.00 157.00   1.00    1.00    --  108.00  61.00  90.00   68
 26  \w     38.00  68.00   1.00    1.00    --  108.00 -94.00 -30.00   30
 27  \w     73.00 110.00   1.00    1.00    --  108.00 -94.00 -30.00   37
 28  \w     82.00 171.00   1.00    1.00    --  108.00  30.00-180.00   89
 29  \w     92.00 150.00   1.00    1.00    --  108.00 178.00 -30.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1173735000
_diffrn_orient_matrix_UB_12      0.0015659000
_diffrn_orient_matrix_UB_13      -0.0998668000
_diffrn_orient_matrix_UB_21      -0.1686706000
_diffrn_orient_matrix_UB_22      0.0466539000
_diffrn_orient_matrix_UB_23      -0.0636452000
_diffrn_orient_matrix_UB_31      0.0154307000
_diffrn_orient_matrix_UB_32      0.1945284000
_diffrn_orient_matrix_UB_33      -0.0008103000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5367
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.046
_diffrn_reflns_theta_max         67.046
_diffrn_reflns_theta_min         3.397
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'blackish colourless'
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0503P)^2^+0.0612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1220
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2010
_reflns_number_total             2719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc03587h2.cif
_cod_data_source_block           202011277
_cod_depositor_comments
'Adding full bibliography for 7244045--7244047.cif.'
_cod_original_cell_volume        762.42(11)
_cod_database_code               7244047
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N2
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.884
_reflns_odcompleteness_completeness 99.89
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.862