Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines
Živković, Marijana B; Matić, Ivana Z; Rodić, Marko V; Novaković, Irena T; Sladić, Dušan; Krstic, Natalija; RSC Adv.  (2016) –; doi:10.1039/C6RA01516F

data_7224700
_publ_section_title
;
 Synthesis, characterization and in vitro cytotoxic activities of new
 steroidal thiosemicarbazones and thiadiazolines
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA01516F
_journal_year                    2016
_chemical_absolute_configuration rm
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C23 H31 N3 O3 S'
_chemical_formula_structural     'C23 H31 N3 O3 S'
_chemical_formula_sum            'C23 H31 N3 O3 S'
_chemical_formula_weight         429.57
_chemical_melting_point          468
_chemical_name_common
N-(3'-acetyl-17-oxospiro[19-norandrost-4-ene-3,2'-[1,3,4]-thiadiazoline]-5'-yl)acetamide
_chemical_name_systematic
N-(3'-acetyl-17-oxospiro[19-norandrost-4-ene-3,2'-[1,3,4]-thiadiazoline]-5'-yl)acetamide
_space_group_IT_number           79
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      79
_symmetry_space_group_name_Hall  'I 4'
_symmetry_space_group_name_H-M   'I 4'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_creation_date             2014-12-06T15:40:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2014-12-06 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.9810(3)
_cell_length_b                   21.9810(3)
_cell_length_c                   10.9904(3)
_cell_measurement_reflns_used    6189
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.449
_cell_measurement_theta_min      3.81
_cell_volume                     5310.17(18)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXLE (H\"ubschle et al., 2011)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 16.328
_diffrn_detector_type            'Sapphire3 (Agilent Technologies)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Agilent Technologies)'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_orient_matrix_UB_11      0.0218708
_diffrn_orient_matrix_UB_12      0.0188137
_diffrn_orient_matrix_UB_13      0.028911
_diffrn_orient_matrix_UB_21      0.0231871
_diffrn_orient_matrix_UB_22      -0.0211092
_diffrn_orient_matrix_UB_23      -0.0152089
_diffrn_orient_matrix_UB_31      0.0050224
_diffrn_orient_matrix_UB_32      0.0155421
_diffrn_orient_matrix_UB_33      -0.0556679
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15692
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.86
_diffrn_reflns_theta_full        26.32
_diffrn_reflns_theta_max         29.119
_diffrn_reflns_theta_min         3.342
_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) (Agilent Technologies)'
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.97466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;  Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm using CrysAlisPro 
 (Agilent Technologies, 2014).
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.075
_exptl_crystal_description       prism
_exptl_crystal_F_000             1840
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Absolute structure was assigned to match known absolute configuration 
 of the steroid core.

 Flack x = 0.05(12) determined by conventional TWIN/BASF refinement 
 (Flack, 1983).

 Flack x = 0.03(3) determined using post-refinement Parsons quotient 
 method (1931 quotients) (Parsons, Flack and Wagner, 2013) 

 Hooft y = 0.04(3) determined using 2769 Bijvoet pairs (9 outliers) 
 (Hooft, Stravera and Spek, 2008) using optimized Student's t-probability
 plot (\n = 99, corr. coeff. = 0.999) (Hooft, Stravera and Spek, 2009)
;
_refine_ls_abs_structure_Flack   0.05(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         6161
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0940P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1486
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.814
_reflns_number_gt                4874
_reflns_number_total             6161
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra01516f2.cif
_cod_data_source_block           4
_cod_original_cell_volume        5310.2(2)
_cod_database_code               7224700
_platon_squeeze_void_probe_radius 1.20
_shelx_res_checksum              31393