Design, synthesis and evaluation of structurally diverse ortho-acylphenol-diindolylmethane hybrids as anticancer agents
Yin, Zhi-Gang; Liu, Xiong-Wei; Wang, Hui-Juan; Zhang, Min; Liu, Xiong-Li; Zhou, Ying; New Journal of Chemistry 46 (2022) 1295–1307; doi:10.1039/D1NJ05170A

data_7061166
_publ_section_title
;
 Design, synthesis and evaluation of structurally diverse
 ortho-acylphenol-diindolylmethane hybrids as anticancer agents
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1295
_journal_page_last               1307
_journal_paper_doi               10.1039/D1NJ05170A
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C25 H18 Br2 N2 O2'
_chemical_formula_sum            'C25 H18 Br2 N2 O2'
_chemical_formula_weight         538.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-17
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-08-27 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.854(2)
_cell_length_b                   22.397(2)
_cell_length_c                   5.6423(5)
_cell_measurement_reflns_used    2756
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.8420
_cell_measurement_theta_min      2.5810
_cell_volume                     2129.8(4)
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_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    -16.00  84.00   1.00    6.50    --   11.90  57.00 -30.00  100
  2  \w     36.00  62.00   1.00    6.50    --   11.90 178.00 150.00   26
  3  \w    -54.00  35.00   1.00    6.50    --   11.90 -57.00-180.00   89
  4  \w    -75.00 -25.00   1.00    6.50    --  -11.27 -77.00  60.00   50
;
_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      -0.0299660000
_diffrn_orient_matrix_UB_12      0.0179023000
_diffrn_orient_matrix_UB_13      0.0524297000
_diffrn_orient_matrix_UB_21      -0.0253645000
_diffrn_orient_matrix_UB_22      -0.0252330000
_diffrn_orient_matrix_UB_23      0.0062955000
_diffrn_orient_matrix_UB_31      0.0152027000
_diffrn_orient_matrix_UB_32      -0.0068032000
_diffrn_orient_matrix_UB_33      0.1140343000
_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  0.0504
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            12574
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.832
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37461
_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    1.679
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 773 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3466
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0279P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0802
_reflns_Friedel_coverage         0.666
_reflns_Friedel_fraction_full    0.834
_reflns_Friedel_fraction_max     0.834
_reflns_number_gt                2498
_reflns_number_total             3466
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj05170a2.cif
_cod_data_source_block           5-5-2
_cod_depositor_comments
'Adding full bibliography for 7061166--7061167.cif.'
_cod_database_code               7061166
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2B), C2(H2A), C4(H4), C5(H5), C8(H8), C11(H11), C14(H14),
 C15(H15), C17(H17), C21(H21), C22(H22), C23(H23), C24(H24)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              444
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.836
_oxdiff_exptl_absorpt_empirical_full_min 0.680