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_7158768
_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         'C22 H18 O2'
_chemical_formula_sum            'C22 H18 O2'
_chemical_formula_weight         314.36
_chemical_name_systematic
2-hydroxy-5-methyl-2,3-diphenyl-2,3-dihydro-1H-inden-1-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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-15 deposited with the CCDC.	2022-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.300(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6355(11)
_cell_length_b                   6.4732(8)
_cell_length_c                   30.237(3)
_cell_measurement_reflns_used    3990
_cell_measurement_temperature    301.41(10)
_cell_measurement_theta_max      28.3910
_cell_measurement_theta_min      3.2000
_cell_volume                     1689.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.41(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.879
_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   8.00   0.25   19.72    --   -7.60  26.00  35.00  100
  2  \w    -29.00  -4.00   0.25   19.72    --   -7.60 -26.00-128.00  100
  3  \w     56.00  96.00   0.25   19.72    --    7.20  77.00  60.00  160
  4  \w    -67.00  14.00   0.25   19.72    --    7.20 -57.00-180.00  324
  5  \w     51.00  90.00   0.25   19.72    --    7.20  77.00-180.00  156
  6  \w     62.00  89.00   0.25   19.72    --    7.20  77.00  90.00  108
  7  \w     -1.00  42.00   0.25   19.72    --    7.20 -82.00-180.00  172
  8  \w    -62.00  19.00   0.25   19.72    --   -7.60 -82.00 -90.00  324
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB 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      0.0532685000
_diffrn_orient_matrix_UB_12      0.0248989000
_diffrn_orient_matrix_UB_13      0.0174041000
_diffrn_orient_matrix_UB_21      -0.0562952000
_diffrn_orient_matrix_UB_22      -0.0264785000
_diffrn_orient_matrix_UB_23      0.0157433000
_diffrn_orient_matrix_UB_31      0.0272651000
_diffrn_orient_matrix_UB_32      -0.1033475000
_diffrn_orient_matrix_UB_33      0.0000601000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1080
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            15595
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.030
_diffrn_reflns_theta_min         3.072
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             664
_exptl_crystal_preparation       xx
_exptl_crystal_recrystallization_method yy
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1370
_refine_ls_R_factor_gt           0.1093
_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^)+(0.0985P)^2^+3.4825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2831
_refine_ls_wR_factor_ref         0.2979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2688
_reflns_number_total             3961
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00595f2.cif
_cod_data_source_block           aj1223
_cod_depositor_comments
'Adding full bibliography for 7158767--7158769.cif.'
_cod_original_cell_volume        1689.8(4)
_cod_database_code               7158768
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHO
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 99.60
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C21(H21), C15(H15), C17(H17), C11(H11), C20(H20),
 C14(H14), C19(H19), C13(H13), C18(H18), C12(H12)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_smtbx_masks_special_details
'A solvent mask was calculated and 2 electrons were found in a volume of 34\%A^3^ in 1 void per unit cell. This is consistent with the presence of 0.05[H2O] per Formula Unit which account for 2 electrons per unit cell.'
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              95139
_shelx_fab_checksum              24752
_olex2_exptl_crystal_mounting_method 'In a cryloop with mineral oil'
_olex2_submission_original_sample_id 'JTK Hydroxy'
_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 1.457
_oxdiff_exptl_absorpt_empirical_full_min 0.582