Quantitative analysis of hydrogen and chalcogen bonds in two pyrimidine-5-carbonitrile derivatives, potential DHFR inhibitors: an integrated crystallographic and theoretical study
Al-Wahaibi, Lamya H.; Chakraborty, Kushumita; Al-Shaalan, Nora H.; Syed Majeed, Mohamed Yehya Annavi; Blacque, Olivier; Al-Mutairi, Aamal A.; El-Emam, Ali A.; Percino, M. Judith; Thamotharan, Subbiah; RSC Advances 10 (2020) 36806–36817; doi:10.1039/D0RA07215J

data_7241372
_publ_section_title
;
 Quantitative analysis of hydrogen and chalcogen bonds in two
 pyrimidine-5-carbonitrile derivatives, potential DHFR inhibitors: an
 integrated crystallographic and theoretical study
;
_journal_issue                   60
_journal_name_full               'RSC Advances'
_journal_page_first              36806
_journal_page_last               36817
_journal_paper_doi               10.1039/D0RA07215J
_journal_volume                  10
_journal_year                    2020
_chemical_formula_sum            'C13 H11 N3 O S'
_chemical_formula_weight         257.31
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-08-08 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                94.308(2)
_cell_angle_beta                 93.766(2)
_cell_angle_gamma                100.924(3)
_cell_formula_units_Z            2
_cell_length_a                   4.6908(2)
_cell_length_b                   9.2376(3)
_cell_length_c                   14.6613(3)
_cell_measurement_reflns_used    7574
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      77.7
_cell_measurement_theta_min      3.0
_cell_volume                     619.95(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      160(1)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13068
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.464
_diffrn_reflns_theta_min         3.033
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.248
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       needle
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0485P)^2^+0.1743P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0888
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2219
_reflns_number_total             2524
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra07215j2.cif
_cod_data_source_block           shelx_CCDC1
_cod_database_code               7241372
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.759
_shelx_estimated_absorpt_t_max   0.956
_shelx_res_checksum              11550