Synthesis, crystal structure and cytotoxic activity of novel 5-methyl-4-thiopyrimidine derivatives
Stolarczyk, Marcin; Bryndal, Iwona; Matera-Witkiewicz, Agnieszka; Lis, Tadeusz; Królewska-Golińska, Karolina; Cieślak, Marcin; Kaźmierczak-Barańska, Julia; Cieplik, Jerzy; Acta Crystallographica Section C 74 (2018) 1138–1145; doi:10.1107/S2053229618012706

data_2021239
_publ_section_title
;
 Synthesis, crystal structure and cytotoxic activity of novel
 5-methyl-4-thiopyrimidine derivatives
;
_journal_coeditor_code           SK3706
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1138
_journal_page_last               1145
_journal_paper_doi               10.1107/S2053229618012706
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C21 H19 Cl N2 O2 S'
_chemical_formula_moiety         'C21 H19 Cl N2 O2 S'
_chemical_formula_sum            'C21 H19 Cl N2 O2 S'
_chemical_formula_weight         398.89
_chemical_melting_point          360
_chemical_name_systematic
;
Ethyl 4-[(4-chlorobenzyl)sulfanyl]-6-methyl-2-phenylpyrimidine-5-carboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                76.05(2)
_cell_angle_beta                 84.86(2)
_cell_angle_gamma                79.63(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8332(18)
_cell_length_b                   10.401(2)
_cell_length_c                   12.166(3)
_cell_measurement_reflns_used    6878
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.9951
_cell_measurement_theta_min      3.0625
_cell_volume                     945.1(4)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2012)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2014)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3359
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Agilent Xcalibur Sapphire2, large Be window'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8817
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.056
_diffrn_reflns_theta_min         3.069
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent, 2012),
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by Clark & Reid (1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.515
_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     246
_refine_ls_number_reflns         4461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0886P)^2^+0.4144P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1431
_reflns_number_gt                4002
_reflns_number_total             4461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3706sup1.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 2021239--2021241.cif.'
_cod_database_code               2021239
_cod_database_fobs_code          2021239
_shelx_estimated_absorpt_t_min   0.873
_shelx_estimated_absorpt_t_max   0.961
_shelx_hkl_checksum              8583
_shelx_res_checksum              98416