Access to fused π-extended acridone derivatives through a regioselective oxidative demethylation.
Ding, Weiwei; Zhang, Gang; Organic & biomolecular chemistry 19 (2021) 6985–6989; doi:10.1039/d1ob01249e

data_7158198
_publ_section_title
;
 Access to fused \p-extended acridone derivatives through a regioselective
 oxidative demethylation.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6985
_journal_page_last               6989
_journal_paper_doi               10.1039/d1ob01249e
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C25 H25 N O3'
_chemical_formula_sum            'C25 H25 N O3'
_chemical_formula_weight         387.46
_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     dual
_audit_creation_date             2020-12-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-06-11 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                117.309(13)
_cell_angle_beta                 91.977(11)
_cell_angle_gamma                96.236(10)
_cell_formula_units_Z            2
_cell_length_a                   8.6227(10)
_cell_length_b                   11.3588(12)
_cell_length_c                   11.8411(17)
_cell_measurement_reflns_used    2308
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.3650
_cell_measurement_theta_min      4.1440
_cell_volume                     1019.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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     28.00  69.00   1.00    2.00    --   40.73 -57.00 120.00   41
  2  \w     27.00 109.00   1.00    4.00    --  107.58 -95.00 150.00   82
  3  \w     36.00 105.00   1.00    4.00    --  107.58 -95.00  60.00   69
  4  \w    111.00 136.00   1.00    4.00    --  107.58 -61.00 -30.00   25
  5  \w     66.00 108.00   1.00    4.00    --  107.58 -95.00 -60.00   42
  6  \w     59.00  87.00   1.00    4.00    --  107.58 -61.00 -30.00   28
  7  \w     57.00 104.00   1.00    4.00    --  107.58 -95.00-120.00   47
  8  \w     54.00  81.00   1.00    2.00    --   40.73-125.00 -60.00   27
  9  \w     42.00 129.00   1.00    4.00    --  107.58 -45.00-120.00   87
 10  \w    112.00 172.00   1.00    4.00    --  107.58  45.00-180.00   60
 11  \w     80.00 140.00   1.00    4.00    --  107.58  61.00 -90.00   60
 12  \w     36.00 132.00   1.00    4.00    --  107.58 -45.00 120.00   96
 13  \w     26.00 155.00   1.00    4.00    --  107.58 -15.00   0.00  129
 14  \w     18.00  68.00   1.00    2.00    --   40.73  38.00-180.00   50
 15  \w    -94.00  -3.00   1.00    2.00    --  -40.73 125.00  30.00   91
 16  \w   -114.00 -28.00   1.00    2.00    --  -40.73 -38.00 -30.00   86
 17  \w   -108.00 -13.00   1.00    2.00    --  -40.73 -57.00-120.00   95
 18  \w     17.00  43.00   1.00    8.00    --   40.98  38.00-180.00   26
 19  \w     85.00 110.00   1.00   10.00    --  107.58 -95.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0379989000
_diffrn_orient_matrix_UB_12      -0.1208842000
_diffrn_orient_matrix_UB_13      0.0255010000
_diffrn_orient_matrix_UB_21      -0.0297539000
_diffrn_orient_matrix_UB_22      0.0948920000
_diffrn_orient_matrix_UB_23      0.1381082000
_diffrn_orient_matrix_UB_31      -0.1739921000
_diffrn_orient_matrix_UB_32      -0.0122513000
_diffrn_orient_matrix_UB_33      -0.0437550000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6322
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.597
_diffrn_reflns_theta_max         66.597
_diffrn_reflns_theta_min         4.221
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0936
_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^)+(0.1783P)^2^+1.1515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2981
_refine_ls_wR_factor_ref         0.3188
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2716
_reflns_number_total             3591
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01249e2.cif
_cod_data_source_block           dw-190_2
_cod_depositor_comments
'Adding full bibliography for 7158198--7158200.cif.'
_cod_original_cell_volume        1019.7(2)
_cod_database_code               7158198
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C13(H13), C17(H17), C18(H18),
 C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              1500
_olex2_date_sample_data_collection 2020-12-25
_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 1.662
_oxdiff_exptl_absorpt_empirical_full_min 0.383