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_7247358
_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         'C25 H18 N2 O2'
_chemical_formula_sum            'C25 H18 N2 O2'
_chemical_formula_weight         378.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-13
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.1217(2)
_cell_length_b                   17.3684(4)
_cell_length_c                   23.9176(6)
_cell_measurement_reflns_used    21489
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9600
_cell_measurement_theta_min      1.7240
_cell_volume                     3789.25(15)
_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 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    -17.00 100.00   0.50   21.63    --   10.60  82.00 150.00  234
  2  \w    -17.00 100.00   0.50   21.63    --   10.60  82.00-180.00  234
  3  \w   -100.00  15.00   0.50   21.63    --  -10.90 -77.00-150.00  230
  4  \w   -100.00  17.00   0.50   21.63    --  -10.90 -82.00  90.00  234
  5  \w   -100.00  20.00   0.50   21.63    --  -10.90 -57.00-150.00  240
  6  \w    -35.00  39.00   0.50   21.63    --  -10.90  66.00 128.93  148
;
_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      -0.0037169000
_diffrn_orient_matrix_UB_12      0.0260732000
_diffrn_orient_matrix_UB_13      -0.0278121000
_diffrn_orient_matrix_UB_21      0.0019639000
_diffrn_orient_matrix_UB_22      0.0732338000
_diffrn_orient_matrix_UB_23      0.0098559000
_diffrn_orient_matrix_UB_31      0.0406268000
_diffrn_orient_matrix_UB_32      -0.0011708000
_diffrn_orient_matrix_UB_33      -0.0029915000
_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  0.0853
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            37185
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.068
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45457
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         6443
_refine_ls_number_restraints     1663
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0621
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1215P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1582
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                5747
_reflns_number_total             6443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02364h2.cif
_cod_data_source_block           k11008-jjw-f(nc-en-a2c)
_cod_depositor_comments
;
Adding full bibliography for 7247352--7247359.cif.

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C11.76 H8.47 N0.94 O0.94'
_cod_original_formula_weight         178.08
_cod_original_formula_moiety         '0.47(C25 H18 N2 O2)'
_cod_original_formula_units_Z            17
_cod_database_code               7247358
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.979
_diffrn_oxdiff_digest_frames
;
01a28e717088c294ea381bee1f025fc726000251fd6
;
_diffrn_oxdiff_digest_hkl
;
0176f2c6d99a6258b4b550f6df3dec45d31ce2
;
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 3(2)
 -2(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33
\\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41
\\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49
\\sim C50 \\sim N1 \\sim N2 \\sim N3 \\sim N4 \\sim O1 \\sim O2 \\sim O3 \\sim
O4: within 3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C10(H10), C35(H35)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C34(H34A,H34B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), N3(H3),
 C29(H29), C30(H30), C31(H31), C32(H32), C37(H37), C38(H38), C39(H39), C40(H40),
  C41(H41), C45(H45), C46(H46), C47(H47), C48(H48), C49(H49)
;
_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 2.775
_oxdiff_exptl_absorpt_empirical_full_min 0.605