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_7158200
_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         '2(C H Cl3), C34 H27 N3 O2'
_chemical_formula_sum            'C36 H29 Cl6 N3 O2'
_chemical_formula_weight         748.32
_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             2021-01-16
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-06-11 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                101.203(4)
_cell_angle_beta                 101.376(3)
_cell_angle_gamma                103.039(3)
_cell_formula_units_Z            2
_cell_length_a                   11.5804(4)
_cell_length_b                   12.1813(6)
_cell_length_c                   12.9925(5)
_cell_measurement_reflns_used    5571
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.3910
_cell_measurement_theta_min      3.5610
_cell_volume                     1694.85(13)
_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-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.966
_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    -60.00  29.00   1.00    1.00    --  -40.73  57.00  60.00   89
  2  \w     31.00  74.00   1.00    1.00    --   40.73-125.00 -30.00   43
  3  \w     27.00  54.00   1.00    1.00    --   40.73-125.00-120.00   27
  4  \w     28.00  93.00   1.00    1.00    --   40.73-125.00-180.00   65
  5  \w     41.00 130.00   1.00    1.00    --  107.58 -61.00-180.00   89
  6  \w     84.00 116.00   1.00    1.00    --  107.58-125.00 -60.00   32
  7  \w     42.00 138.00   1.00    1.00    --  107.58 -77.00 -60.00   96
  8  \w     83.00 117.00   1.00    1.00    --  107.58  45.00  90.00   34
  9  \w    140.00 172.00   1.00    1.00    --  107.58  45.00  90.00   32
 10  \w     99.00 147.00   1.00    1.00    --  107.58  45.00 150.00   48
 11  \w     60.00 107.00   1.00    1.00    --  107.58 -94.00 150.00   47
 12  \w     69.00 121.00   1.00    1.00    --  107.58-125.00 120.00   52
 13  \w     35.00 132.00   1.00    1.00    --  107.58 -45.00  60.00   97
 14  \w     39.00 136.00   1.00    1.00    --  107.58 -30.00 -90.00   97
 15  \w     39.00 155.00   1.00    1.00    --  107.58 -15.00 120.00  116
 16  \w   -129.00  35.00   1.00    1.00    --  -40.73   0.00-120.00  164
;
_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      0.0634279000
_diffrn_orient_matrix_UB_12      -0.0119165000
_diffrn_orient_matrix_UB_13      -0.0936561000
_diffrn_orient_matrix_UB_21      0.0053484000
_diffrn_orient_matrix_UB_22      -0.1228141000
_diffrn_orient_matrix_UB_23      0.0100311000
_diffrn_orient_matrix_UB_31      -0.1259462000
_diffrn_orient_matrix_UB_32      -0.0524479000
_diffrn_orient_matrix_UB_33      -0.0820491000
_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  0.0314
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11542
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.963
_diffrn_reflns_theta_min         3.584
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.935
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57483
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         6648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0558P)^2^+0.9297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1267
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5534
_reflns_number_total             6648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01249e2.cif
_cod_data_source_block           dw218
_cod_depositor_comments
'Adding full bibliography for 7158198--7158200.cif.'
_cod_database_code               7158200
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.98
_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 Ternary CH refined with riding coordinates:
 C35(H35), C36(H36)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C20(H20), C26(H26), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              74037
_olex2_date_sample_data_collection 2021-01-16
_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 2.192
_oxdiff_exptl_absorpt_empirical_full_min 0.760