Synthesis, structure, and antitumor activity of 2,9-disubstituted perhydro 2,3a,7b,9,10a,14b-hexaazadibenzotetracenes
Rakhimova, Elena B.; Kirsanov, Victor Yu.; Tret'yakova, Elena V.; Khalilov, Leonard M.; Ibragimov, Askhat G.; Dzhemileva, Lilya U.; D'yakonov, Vladimir A.; Dzhemilev, Usein M.; RSC Advances 10 (2020) 21039–21048; doi:10.1039/D0RA03209C

data_7240635
_publ_section_title
;
 Synthesis, structure, and antitumor activity of 2,9-disubstituted
 perhydro 2,3a,7b,9,10a,14b-hexaazadibenzotetracenes
;
_journal_issue                   36
_journal_name_full               'RSC Advances'
_journal_page_first              21039
_journal_page_last               21048
_journal_paper_doi               10.1039/D0RA03209C
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C32 H56 N6, 2(C H Cl3)'
_chemical_formula_sum            'C34 H58 Cl6 N6'
_chemical_formula_weight         763.56
_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     direct
_audit_creation_date             2019-07-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-23 deposited with the CCDC.	2020-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                78.370(9)
_cell_angle_beta                 85.218(8)
_cell_angle_gamma                72.376(9)
_cell_formula_units_Z            2
_cell_length_a                   10.1228(10)
_cell_length_b                   10.5481(11)
_cell_length_c                   19.5768(19)
_cell_measurement_reflns_used    1756
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.0750
_cell_measurement_theta_min      2.1040
_cell_volume                     1950.8(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1709
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega    1.00   81.00   1.0000   18.8550
omega____ theta____ kappa____ phi______ frames
    -       16.8699   57.0000  120.0000 80

  2 omega  -20.00   22.00   1.0000   18.8550
omega____ theta____ kappa____ phi______ frames
    -      -16.0886  -99.0000  -60.0000 42

  3 omega  -37.00   29.00   1.0000   18.8550
omega____ theta____ kappa____ phi______ frames
    -       16.8699  -57.0000 -150.0000 66

  4 omega   23.00   58.00   1.0000   18.8550
omega____ theta____ kappa____ phi______ frames
    -       16.8699   57.0000 -180.0000 35

  5 omega  -51.00   44.00   1.0000   18.8550
omega____ theta____ kappa____ phi______ frames
    -       16.8699  -77.0000    0.0000 95

  6 omega  -89.00  -32.00   1.0000   18.8550
omega____ theta____ kappa____ phi______ frames
    -      -16.0886  178.0000 -180.0000 57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0180795000
_diffrn_orient_matrix_UB_12      0.0707657000
_diffrn_orient_matrix_UB_13      -0.0009860000
_diffrn_orient_matrix_UB_21      -0.0519370000
_diffrn_orient_matrix_UB_22      -0.0051928000
_diffrn_orient_matrix_UB_23      0.0261704000
_diffrn_orient_matrix_UB_31      0.0488256000
_diffrn_orient_matrix_UB_32      -0.0110050000
_diffrn_orient_matrix_UB_33      0.0261394000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_unetI/netI     0.2015
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16427
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.249
_diffrn_reflns_theta_min         2.112
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'Agilent XCalibur (EOS, Gemini)'
_exptl_absorpt_coefficient_mu    0.473
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       plank
_exptl_crystal_F_000             812.0
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.872
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         8968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.872
_refine_ls_R_factor_all          0.2600
_refine_ls_R_factor_gt           0.0751
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1721
_refine_ls_wR_factor_ref         0.2723
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2594
_reflns_number_total             8968
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra03209c2.cif
_cod_data_source_block           kvy-83-24
_cod_depositor_comments          'Adding full bibliography for 7240635.cif.'
_cod_database_code               7240635
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C14E(H14E), C14D(H14D), C10B(H10C), C14A(H14A), C3B(H3B),
 C1''(H1''), C7A(H7A), C1'(H1'), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C8(H8A,H8B), C3(H3A,H3C), C1(H1A,H1B), C7(H7B,H7C), C11(H11A,
 H11B), C14(H14B,H14C), C7'(H7'A,H7'B), C13(H13A,H13B), C7''(H7'C,H7'D),
 C12(H12A,H12B), C6(H6A,H6B), C4(H4A,H4B), C2'(H2'A,H2'B), C5(H5A,H5B),
 C6''(H6'A,H6'B), C2''(H2'C,H2'D), C3''(H3'A,H3'B), C3'(H3'C,H3'D), C4''(H4'A,
 H4'B), C6'(H6'C,H6'D), C5'(H5'A,H5'B), C4'(H4'C,H4'D), C5''(H5'C,H5'D)
;