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_7244045
_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         'C18 H13 N3'
_chemical_formula_sum            'C18 H13 N3'
_chemical_formula_weight         271.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-07-10
_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                90
_cell_angle_beta                 103.542(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.9525(3)
_cell_length_b                   12.9657(4)
_cell_length_c                   20.7069(7)
_cell_measurement_reflns_used    2094
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7080
_cell_measurement_theta_min      5.3600
_cell_volume                     2858.77(16)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -104.00 -11.00   1.00    2.00    --  -33.50 -37.00 120.00   93
  2  \w   -101.00 -34.00   1.00    2.00    --  -33.50 178.00  90.00   67
  3  \w     51.00 100.00   1.00    2.00    --   36.47  19.00-180.00   49
  4  \w    -31.00   7.00   1.00    2.00    --   36.47 -57.00  60.00   38
  5  \w     59.00  85.00   1.00    2.00    --   36.47 178.00   0.00   26
  6  \w     63.00  90.00   1.00    2.00    --   36.47 178.00 -30.00   27
  7  \w     58.00 108.00   1.00    2.00    --   36.47 178.00  60.00   50
  8  \w     20.00  55.00   1.00    2.00    --   36.47 -57.00  60.00   35
  9  \w      6.00  38.00   1.00    2.00    --   36.47  19.00-180.00   32
 10  \w     54.00  81.00   1.00    5.00    --  108.00 -94.00   0.00   27
 11  \w     39.00 133.00   1.00    5.00    --  108.00 -30.00-180.00   94
 12  \w    103.00 141.00   1.00    5.00    --  108.00  61.00  30.00   38
 13  \w     39.00 101.00   1.00    5.00    --  108.00 -45.00  60.00   62
 14  \w     57.00 109.00   1.00    5.00    --  108.00 -94.00  90.00   52
 15  \w     89.00 173.00   1.00    5.00    --  108.00  45.00   0.00   84
 16  \w    122.00 148.00   1.00    5.00    --  108.00  45.00 -60.00   26
 17  \w    127.00 178.00   1.00    5.00    --  108.00 111.00  90.00   51
 18  \w    100.00 150.00   1.00    5.00    --  108.00 111.00-150.00   50
;
_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      0.0299199000
_diffrn_orient_matrix_UB_12      -0.0113615000
_diffrn_orient_matrix_UB_13      0.0761446000
_diffrn_orient_matrix_UB_21      -0.1171140000
_diffrn_orient_matrix_UB_22      -0.0684518000
_diffrn_orient_matrix_UB_23      -0.0059173000
_diffrn_orient_matrix_UB_31      0.0795031000
_diffrn_orient_matrix_UB_32      -0.0964873000
_diffrn_orient_matrix_UB_33      -0.0047284000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5277
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         4.393
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96158
_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    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0574P)^2^+0.7675P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1230
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2064
_reflns_number_total             2555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc03587h2.cif
_cod_data_source_block           20200787
_cod_depositor_comments
'Adding full bibliography for 7244045--7244047.cif.'
_cod_original_cell_volume        2858.76(16)
_cod_database_code               7244045
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C14H15N2
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.900
_reflns_odcompleteness_completeness 99.96
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16)
;
_shelx_res_checksum              93776
_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 1.142
_oxdiff_exptl_absorpt_empirical_full_min 0.845