Arylbiamidines: synthesis and structural studies en route to anticancer applications
Grytsai, Oleksandr; Gonçalves, Leticia Christina Pires; Bardovskyi, Rostyslav; Hamouda-Tekaya, Nedra; Rocchi, Stéphane; Ronco, Cyril; Benhida, Rachid; New Journal of Chemistry 45 (2021) 11893–11897; doi:10.1039/D1NJ01943K

data_7060704
_publ_section_title
;
 Arylbiamidines: synthesis and structural studies en route to anticancer
 applications
;
_journal_issue                   27
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11893
_journal_page_last               11897
_journal_paper_doi               10.1039/D1NJ01943K
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C13 H15 N5 S'
_chemical_formula_sum            'C13 H15 N5 S'
_chemical_formula_weight         273.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-06-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-05 deposited with the CCDC.	2021-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.519(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8884(4)
_cell_length_b                   10.9455(5)
_cell_length_c                   12.6252(5)
_cell_measurement_reflns_used    4566
_cell_measurement_temperature    295
_cell_measurement_theta_max      72.3470
_cell_measurement_theta_min      4.4220
_cell_volume                     1365.99(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.79a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.79a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.79a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_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   -115.00 -48.00   1.00    1.00    --  -40.16 -37.00  40.00   67
  2  \w    -60.00  31.00   1.00    1.00    --  -40.16  37.00-163.00   91
  3  \w     -9.00  16.00   1.00    1.00    --   40.16 -37.00  40.00   25
  4  \w     70.00 115.00   1.00    1.00    --   40.16  37.00-163.00   45
  5  \w    129.00 174.00   1.00   20.00    --  105.59  37.00-163.00   45
  6  \w     62.00 122.00   1.00   20.00    --  105.59 -37.00  40.00   60
  7  \w    -82.00 -51.00   1.00    1.00    --  -40.16 -38.00-150.00   31
  8  \w    -59.00 -22.00   1.00    1.00    --  -40.16 -38.00 -60.00   37
  9  \w    -63.00 -35.00   1.00    1.00    --  -40.16 -19.00 -90.00   28
 10  \w   -111.00 -13.00   1.00    1.00    --  -40.16 -57.00 -90.00   98
 11  \w     35.00  60.00   1.00    1.00    --   40.16  38.00 -30.00   25
 12  \w     23.00  86.00   1.00    1.00    --   40.16-125.00 -90.00   63
 13  \w     27.00  94.00   1.00    1.00    --   40.16-125.00-180.00   67
 14  \w     74.00 102.00   1.00   20.00    --  105.59  77.00 -60.00   28
 15  \w    146.00 177.00   1.00   20.00    --  105.59  61.00-120.00   31
 16  \w     25.00 109.00   1.00   20.00    --  105.59 -94.00  90.00   84
 17  \w    110.00 137.00   1.00   20.00    --  105.59 125.00-180.00   27
 18  \w     96.00 124.00   1.00   20.00    --  105.59 125.00  90.00   28
 19  \w     76.00 103.00   1.00   20.00    --  105.59  61.00 -90.00   27
 20  \w     77.00 105.00   1.00   20.00    --  105.59  61.00 -60.00   28
 21  \w     76.00 104.00   1.00   20.00    --  105.59  61.00 -30.00   28
 22  \w     74.00 100.00   1.00   20.00    --  105.59  77.00 -90.00   26
 23  \w     76.00 145.00   1.00   20.00    --  105.59  61.00-120.00   69
 24  \w     77.00 105.00   1.00   20.00    --  105.59  58.00 -78.99   28
 25  \w     75.00 100.00   1.00   20.00    --  105.59  77.00-150.00   25
 26  \w    118.00 143.00   1.00   20.00    --  105.59  77.00-150.00   25
 27  \w     75.00 103.00   1.00   20.00    --  105.59  75.00 -67.53   28
 28  \w     80.00 130.00   1.00   20.00    --  105.59  45.00   0.00   50
 29  \w     74.00 102.00   1.00   20.00    --  105.59  77.00-120.00   28
 30  \w    149.00 178.00   1.00   20.00    --  105.59 125.00  30.00   29
 31  \w     23.00  95.00   1.00   20.00    --  105.59 -94.00-150.00   72
 32  \w     73.00 100.00   1.00   20.00    --  105.59  77.00 -30.00   27
 33  \w     79.00 107.00   1.00   20.00    --  105.59  30.00 -30.00   28
 34  \w     81.00 176.00   1.00   20.00    --  105.59  45.00 -90.00   95
 35  \w     83.00 116.00   1.00   20.00    --  105.59  45.00 -30.00   33
 36  \w    122.00 163.00   1.00   20.00    --  105.59  45.00 -30.00   41
 37  \w     81.00 106.00   1.00   20.00    --  105.59  45.00 -36.04   25
 38  \w    113.00 138.00   1.00   20.00    --  105.59  77.00 -60.00   25
 39  \w    115.00 178.00   1.00   20.00    --  105.59  61.00   0.00   63
 40  \w     33.00 111.00   1.00   20.00    --  105.59 -45.00-150.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0680615000
_diffrn_orient_matrix_UB_12      -0.0301162000
_diffrn_orient_matrix_UB_13      0.1053017000
_diffrn_orient_matrix_UB_21      -0.1321597000
_diffrn_orient_matrix_UB_22      0.0594253000
_diffrn_orient_matrix_UB_23      -0.0418839000
_diffrn_orient_matrix_UB_31      -0.0468496000
_diffrn_orient_matrix_UB_32      -0.1238932000
_diffrn_orient_matrix_UB_33      -0.0455128000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12086
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.626
_diffrn_reflns_theta_min         4.473
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.054
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.79a (Rigaku Oxford Diffraction, 2020)
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    1.329
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0723P)^2^+0.2669P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1294
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2062
_reflns_number_total             2689
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj01943k2.cif
_cod_data_source_block           mtf303
_cod_depositor_comments          'Adding full bibliography for 7060704.cif.'
_cod_original_cell_volume        1365.98(10)
_cod_database_code               7060704
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.887
_shelx_estimated_absorpt_t_min   0.735
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Others
 Fixed Sof: H12A(0.5) H12B(0.5) H12C(0.5) H12D(0.5) H12E(0.5) H12F(0.5)
 H13A(0.5) H13B(0.5) H13C(0.5) H13D(0.5) H13E(0.5) H13F(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
3.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N3(H3A,H3B)
3.c Disordered Me refined as rotating group:
 C12(H12A,H12B,H12C,H12D,H12E,H12F), C13(H13A,H13B,H13C,H13D,H13E,H13F)
;
_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 1.204
_oxdiff_exptl_absorpt_empirical_full_min 0.823