Solvent controlled synthesis of 2,3-diarylepoxy indenones and α-hydroxy diarylindanones and their evaluation as inhibitors of DNA alkylation repair.
Negi, Rollania; Jena, Tapan Kumar; Jyoti, ?; Tuti, Nikhil Kumar; Anindya, Roy; Khan, Faiz Ahmed; Organic & biomolecular chemistry 20 (2022) 5820–5835; doi:10.1039/d2ob00595f

data_7158769
_publ_section_title
;
 Solvent controlled synthesis of 2,3-diarylepoxy indenones and \a-hydroxy
 diarylindanones and their evaluation as inhibitors of DNA alkylation
 repair.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5820
_journal_page_last               5835
_journal_paper_doi               10.1039/d2ob00595f
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C24 H20 O2'
_chemical_formula_sum            'C24 H20 O2'
_chemical_formula_weight         340.43
_chemical_name_systematic
1a,6a-di-m-tolyl-1a,6a-dihydro-6H-indeno[1,2-b]oxiren-6-one
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-15 deposited with the CCDC.	2022-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.691(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.013(2)
_cell_length_b                   10.9258(16)
_cell_length_c                   19.1838(15)
_cell_measurement_reflns_used    3467
_cell_measurement_temperature    293
_cell_measurement_theta_max      29.0538
_cell_measurement_theta_min      2.9295
_cell_volume                     3767.7(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.9608
_diffrn_measured_fraction_theta_max 0.9608
_diffrn_measurement_details
;
  1 omega  -37.00   -2.00   1.0000   34.7600
omega____ theta____ kappa____ phi______ frames
    -      -17.7643   57.0000  -90.0000 35

  2 omega   39.00   94.00   1.0000   34.7600
omega____ theta____ kappa____ phi______ frames
    -       19.6393  178.0000  150.0000 55

  3 omega  -13.00   25.00   1.0000   34.7600
omega____ theta____ kappa____ phi______ frames
    -       19.6393  -99.0000  -90.0000 38

  4 omega   35.00   62.00   1.0000   34.7600
omega____ theta____ kappa____ phi______ frames
    -       19.6393  -99.0000   90.0000 27

  5 omega  -29.00   91.00   1.0000   34.7600
omega____ theta____ kappa____ phi______ frames
    -       19.6393    0.0000   60.0000 120
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0336985000
_diffrn_orient_matrix_UB_12      0.0037307000
_diffrn_orient_matrix_UB_13      0.0211193000
_diffrn_orient_matrix_UB_21      -0.0174686000
_diffrn_orient_matrix_UB_22      0.0391779000
_diffrn_orient_matrix_UB_23      0.0235165000
_diffrn_orient_matrix_UB_31      -0.0107299000
_diffrn_orient_matrix_UB_32      -0.0516997000
_diffrn_orient_matrix_UB_33      0.0193392000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19874
_diffrn_reflns_theta_full        29.1048
_diffrn_reflns_theta_max         29.10
_diffrn_reflns_theta_min         2.93
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pinkish pink'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   pinkish
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.2002
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1440.6802
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.3543
_refine_diff_density_min         -0.6391
_refine_diff_density_rms         0.1156
_refine_ls_d_res_high            0.7306
_refine_ls_d_res_low             6.9411
_refine_ls_goodness_of_fit_ref   1.1824
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    68
_refine_ls_number_parameters     475
_refine_ls_number_reflns         8706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1824
_refine_ls_R_factor_all          0.2157
_refine_ls_R_factor_gt           0.1190
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3577
_refine_ls_wR_factor_ref         0.4399
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -24
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              -15
_reflns_number_gt                3591
_reflns_number_total             8706
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2ob00595f2.cif
_cod_data_source_block           exp_8187
_cod_depositor_comments
'Adding full bibliography for 7158767--7158769.cif.'
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7158769
_chemical_oxdiff_formula         'C20 H20 O4 Br'
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C21(H21), C0ba(H0ba), C1ba(H1ba), C17(H17), C11(H11), C0aa(H0aa), C19(H19),
 C7(H7), C4(H4), C15(H15), C31(H31), C32(H32), C13(H13), C37(H37), C14(H14),
 C40(H40), C41(H41), C6(H6), C43(H43), C47(H47), C18(H18), C44(H44)
2.b Idealised Me refined as rotating group:
 C36(H36a,H36b,H36c), C22(H22a,H22b,H22c), C23(H23a,H23b,H23c), C24(H24a,H24b,
 H24c), C3aa(H3aa,H3ab,H3ac), C2aa(H2aa,H2ab,H2ac)
;
_olex2_submission_special_instructions 'No special instructions were received'