Molecular Editing of NSC-666719 Enabling Discovery of benzodithiazinedioxide-guanidines as Anticancer Agents
Krishna Rao, Vajja; Paul, Subarno; Gulkis, Mitchell; Shen, Zhihang; Nair, Haritha; Singh, Amandeep; Li, Chenglong; Sharma, Arun K.; Çağlayan, Melike; Das, Chinmay; Das, Biswajit; Kundu, Chanakya Nath; Narayan, Satya; Guchhait, Sankar Kumar; RSC Medicinal Chemistry  (2024) –; doi:10.1039/D3MD00648D

data_7248059
_publ_section_title
;
 Molecular Editing of NSC-666719 Enabling Discovery of
 benzodithiazinedioxide-guanidines as Anticancer Agents
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D3MD00648D
_journal_year                    2024
_chemical_formula_moiety         'C16 H15 Cl N4 O3 S2'
_chemical_formula_sum            'C16 H15 Cl N4 O3 S2'
_chemical_formula_weight         410.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-05-04
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_audit_update_record
;
2023-06-14 deposited with the CCDC.	2024-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.120(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.8739(6)
_cell_length_b                   9.36039(17)
_cell_length_c                   14.3273(3)
_cell_measurement_reflns_used    8244
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1180
_cell_measurement_theta_min      3.4390
_cell_volume                     3460.96(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.945
_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    -38.00  14.00   0.50   12.00    --   -9.95 103.00 -66.00  104
  2  \w     -9.00  16.00   0.50   12.00    --   10.22-103.00-169.00   50
  3  \w    -58.00  -3.00   0.50   12.00    --   -9.95 125.00  30.00  110
  4  \w    -47.00  -4.00   0.50   12.00    --   -9.95 125.00  60.00   86
  5  \w    -68.00 -10.00   0.50   12.00    --   -9.95 -38.00-180.00  116
  6  \w    -57.00  -5.00   0.50   12.00    --   -9.95 125.00-120.00  104
  7  \w    -23.00  49.00   0.50   12.00    --   -9.95  38.00-180.00  144
  8  \w    -28.00  -3.00   0.50   12.00    --   -9.95 125.00   0.00   50
  9  \w      7.00  78.00   0.50   12.00    --   10.22  19.00  90.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13987
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         3.158
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_description       rod
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3343
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0463P)^2^+1.2171P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2807
_reflns_number_total             3343
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3md00648d2.cif
_cod_data_source_block           ex-skg-66-2
_cod_database_code               7248059
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C6(H6), C3(H3A), C10(H10), C14(H14), C13(H13), C11(H11)
2.b X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C15(H15A,H15B,H15C)
;
_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
;