Photocatalyst- and transition-metal-free syntheses of furan-fused dihydroazepines by visible light
Gore, Babasaheb Sopan; Kuo, Chiao-Ying; Wang, Jeh-Jeng; Green Chemistry 25 (2023) 8074–8081; doi:10.1039/D3GC02364H

data_7247356
_publ_section_title
;
 Photocatalyst- and transition-metal-free syntheses of furan-fused
 dihydroazepines by visible light
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              8074
_journal_page_last               8081
_journal_paper_doi               10.1039/D3GC02364H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C35 H32 N2 O'
_chemical_formula_sum            'C35 H32 N2 O'
_chemical_formula_weight         496.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-28
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-06-29 deposited with the CCDC.	2023-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.405(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9969(6)
_cell_length_b                   12.1767(6)
_cell_length_c                   18.3724(11)
_cell_measurement_reflns_used    8272
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.8340
_cell_measurement_theta_min      1.8510
_cell_volume                     2610.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_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    -22.00  80.00   0.50   35.33    --   10.60  54.00-148.00  204
  2  \w    -24.00   7.00   0.50   35.33    --   10.60 -54.00  67.00   62
  3  \w     -5.00  27.00   0.50   35.33    --  -10.90  54.00-148.00   64
  4  \w    -45.00 -19.00   0.50   35.33    --  -10.90 -54.00  67.00   52
  5  \w      3.00  29.00   0.50   35.33    --   10.60  77.00 -60.00   52
  6  \w    -12.00 100.00   0.50   35.33    --   10.60  77.00 -90.00  224
  7  \w     -4.00  81.00   0.50   35.33    --   10.60  77.00 120.00  170
  8  \w     68.00  94.00   0.50   35.33    --   10.60  77.00 -60.00   52
  9  \w    -20.00 100.00   0.50   35.33    --   10.60  57.00 -90.00  240
 10  \w     70.00  96.00   0.50   35.33    --   10.60  77.00 -30.00   52
 11  \w    -36.00  76.00   0.50   35.33    --  -10.90  77.00 -30.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0417797000
_diffrn_orient_matrix_UB_12      -0.0160140000
_diffrn_orient_matrix_UB_13      0.0196228000
_diffrn_orient_matrix_UB_21      -0.0031277000
_diffrn_orient_matrix_UB_22      -0.0527423000
_diffrn_orient_matrix_UB_23      -0.0167653000
_diffrn_orient_matrix_UB_31      0.0440730000
_diffrn_orient_matrix_UB_32      -0.0188402000
_diffrn_orient_matrix_UB_33      0.0301314000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0796
_diffrn_reflns_av_unetI/netI     0.0654
_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       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28253
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.024
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
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    1.263
_exptl_crystal_description       plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4594
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0590
_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^)+(0.0913P)^2^+0.6101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1723
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3329
_reflns_number_total             4594
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02364h2.cif
_cod_data_source_block           k11104-jjw-c(nc-en-12)
_cod_depositor_comments
'Adding full bibliography for 7247352--7247359.cif.'
_cod_database_code               7247356
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C N O H'
_diffrn_oxdiff_digest_frames
;
0121bf957a523d67ac758c0c07c3b8505700025d594
;
_diffrn_oxdiff_digest_hkl
;
012fc926fc7b1d9e98f0c7f59199b2b7b1afc7
;
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
N1 \\sim N2 \\sim O1: within 3.8A with sigma of 0.01 and sigma for terminal
atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C19(H19), C28(H28), C30(H30), C32(H32)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C27(H27A,H27B), C29(H29A,H29B), C31(H31A,H31B), C33(H33A,
 H33B), C34(H34A,H34B), C35(H35A,H35B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_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 2.937
_oxdiff_exptl_absorpt_empirical_full_min 0.439