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_7244046
_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 Br N2 O2'
_chemical_formula_sum            'C19 H15 Br N2 O2'
_chemical_formula_weight         383.24
_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     iterative
_audit_creation_date             2020-12-18
_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                77.749(6)
_cell_angle_beta                 79.907(7)
_cell_angle_gamma                65.413(7)
_cell_formula_units_Z            2
_cell_length_a                   8.5331(6)
_cell_length_b                   9.1322(6)
_cell_length_c                   11.9513(10)
_cell_measurement_reflns_used    3198
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6930
_cell_measurement_theta_min      3.7860
_cell_volume                     823.62(12)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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     -3.00  25.00   1.00    1.00    --    0.00  57.00 120.00   28
  2  \w    -39.00  14.00   1.00    1.00    --    0.00 -57.00 -90.00   53
  3  \w    -52.00  -5.00   1.00    1.00    --  -33.50 -77.00 120.00   47
  4  \w   -101.00 -75.00   1.00    1.00    --  -33.50 -77.00 120.00   26
  5  \w    -34.00  -8.00   1.00    1.00    --  -33.50 -77.00-120.00   26
  6  \w    -82.00 -52.00   1.00    1.00    --  -33.50 -77.00-120.00   30
  7  \w     18.00  48.00   1.00    1.00    --   36.47 -57.00 120.00   30
  8  \w     -2.00  66.00   1.00    1.00    --   36.47 -99.00-120.00   68
  9  \w    -21.00   8.00   1.00    1.00    --   36.47 -57.00 120.00   29
 10  \w     23.00  74.00   1.00    1.00    --   36.47 -99.00 -90.00   51
 11  \w    -13.00  46.00   1.00    1.00    --   36.47 -77.00 -30.00   59
 12  \w     72.00 106.00   1.00    1.00    --   36.47 178.00-150.00   34
 13  \w      5.00  73.00   1.00    1.00    --   36.47 -99.00  60.00   68
 14  \w      7.00  32.00   1.00    1.00    --   44.00  92.00-114.94   25
 15  \w     16.00  41.00   1.00    1.00    --   48.00  83.00  -0.60   25
 16  \w     13.00  38.00   1.00    1.00    --   48.00  88.00  90.26   25
 17  \w     16.00  42.00   1.00    1.00    --   48.00  83.00-138.42   26
 18  \w     15.00  40.00   1.00    1.00    --   48.00  85.00 150.69   25
 19  \w     13.00  38.00   1.00    1.00    --   48.00  88.00  20.98   25
 20  \w     20.00  45.00   1.00    1.00    --   52.00  83.00 -84.39   25
 21  \w     20.00  45.00   1.00    1.00    --   52.00  84.00  54.03   25
 22  \w     30.00 122.00   1.00    1.00    --   56.00  77.00-173.41   92
 23  \w    100.00 125.00   1.00    1.00    --   56.00  77.00 104.21   25
 24  \w     30.00  71.00   1.00    1.00    --   56.00  79.00 -47.44   41
 25  \w     27.00  63.00   1.00    1.00    --   56.00  77.00 104.21   36
 26  \w     33.00  58.00   1.00    1.00    --   56.00  73.00-113.33   25
 27  \w     76.00 124.00   1.00    1.00    --   56.00  79.00 -47.44   48
 28  \w     87.00 124.00   1.00    1.00    --   56.00  73.00-113.33   37
 29  \w     29.00 125.00   1.00    1.00    --   56.00  76.00  11.37   96
 30  \w     34.00  69.00   1.00    1.00    --   60.00  73.00 149.16   35
 31  \w     32.00  74.00   1.00    1.00    --   60.00  75.00  71.39   42
 32  \w     90.00 128.00   1.00    1.00    --   60.00  75.00  71.39   38
 33  \w     35.00  74.00   1.00    1.00    --   60.00  72.00 -78.56   39
 34  \w     83.00 109.00   1.00    1.00    --   60.00  73.00 149.16   26
 35  \w     48.00  91.00   1.00    1.00    --   68.00  62.00 151.05   43
 36  \w    136.00 176.00   1.00    1.50    --  108.00  61.00 120.00   40
 37  \w     79.00 170.00   1.00    1.50    --  108.00  77.00  90.00   91
 38  \w     88.00 114.00   1.00    1.50    --  108.00  61.00 120.00   26
 39  \w     89.00 123.00   1.00    1.50    --  108.00  45.00 150.00   34
 40  \w     41.00 126.00   1.00    1.50    --  108.00 -61.00   0.00   85
 41  \w    121.00 147.00   1.00    1.50    --  108.00 178.00 150.00   26
 42  \w     88.00 130.00   1.00    1.50    --  108.00  61.00  60.00   42
 43  \w     79.00 105.00   1.00    1.50    --  108.00  77.00 -30.00   26
 44  \w     69.00  96.00   1.00    1.50    --  108.00 178.00 150.00   27
 45  \w     88.00 118.00   1.00    1.50    --  108.00  61.00 -30.00   30
 46  \w     88.00 157.00   1.00    1.50    --  108.00  61.00-180.00   69
 47  \w    116.00 174.00   1.00    1.50    --  108.00  77.00  60.00   58
 48  \w     80.00 106.00   1.00    1.50    --  108.00  77.00  60.00   26
 49  \w     81.00 107.00   1.00    1.50    --  108.00  77.00-120.00   26
 50  \w    120.00 171.00   1.00    1.50    --  108.00  77.00 -90.00   51
 51  \w    125.00 162.00   1.00    1.50    --  108.00  61.00 -30.00   37
 52  \w     81.00 107.00   1.00    1.50    --  108.00  77.00-150.00   26
 53  \w     80.00 106.00   1.00    1.50    --  108.00  77.00 -90.00   26
 54  \w     90.00 129.00   1.00    1.50    --  108.00  61.00 -90.00   39
 55  \w     53.00 110.00   1.00    1.50    --  108.00 -94.00 120.00   57
 56  \w     79.00 105.00   1.00    1.50    --  108.00  77.00  30.00   26
 57  \w     79.00 105.00   1.00    1.50    --  108.00  77.00 -60.00   26
 58  \w    116.00 177.00   1.00    1.50    --  108.00  77.00 -60.00   61
 59  \w     79.00 105.00   1.00    1.50    --  108.00  77.00   0.00   26
 60  \w     89.00 171.00   1.00    1.50    --  108.00  61.00-150.00   82
 61  \w     39.00  98.00   1.00    1.50    --  108.00 -94.00-150.00   59
 62  \w     53.00 110.00   1.00    1.50    --  108.00-111.00   0.00   57
 63  \w    123.00 168.00   1.00    1.50    --  108.00  77.00 150.00   45
 64  \w     79.00 105.00   1.00    1.50    --  108.00  77.00-180.00   26
 65  \w     79.00 117.00   1.00    1.50    --  108.00  77.00 150.00   38
 66  \w     88.00 176.00   1.00    1.50    --  108.00  61.00   0.00   88
 67  \w     90.00 116.00   1.00    1.50    --  108.00  61.00 -60.00   26
 68  \w     41.00  96.00   1.00    1.50    --  108.00 -94.00 -90.00   55
 69  \w     91.00 170.00   1.00    1.50    --  108.00  61.00  30.00   79
 70  \w     89.00 164.00   1.00    1.50    --  108.00  61.00-120.00   75
;
_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      0.0239514000
_diffrn_orient_matrix_UB_12      0.1534224000
_diffrn_orient_matrix_UB_13      -0.0689682000
_diffrn_orient_matrix_UB_21      -0.1968917000
_diffrn_orient_matrix_UB_22      0.0865054000
_diffrn_orient_matrix_UB_23      -0.0075430000
_diffrn_orient_matrix_UB_31      -0.0214373000
_diffrn_orient_matrix_UB_32      0.0651808000
_diffrn_orient_matrix_UB_33      0.1129351000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11170
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         3.803
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.514
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66985
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0326P)^2^+0.5982P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0907
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2418
_reflns_number_total             2930
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc03587h2.cif
_cod_data_source_block           202012308
_cod_depositor_comments
'Adding full bibliography for 7244045--7244047.cif.'
_cod_original_cell_volume        823.62(11)
_cod_database_code               7244046
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N2Br1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.720
_shelx_estimated_absorpt_t_min   0.621
_reflns_odcompleteness_completeness 99.73
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              61702
_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 1.613
_oxdiff_exptl_absorpt_empirical_full_min 0.818