Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3H)-ones, Driven under the Umbrella of Sustainable Chemistry
Janković, Nenad; Stefanović, Srđan; Petronijević, Jelena; Joksimović, Nenad; Novaković, Slađana B.; Bogdanović, Goran A.; Muškinja, Jovana; Vraneš, Milan; Ratković, Zoran; Bugarčić, Zorica; ACS Sustainable Chemistry & Engineering 6 (2018) 13358–; doi:10.1021/acssuschemeng.8b03127

data_4517031
_publ_section_title
;
 Water-Tuned Tautomer-Selective Tandem Synthesis of the
 5,6-Dihydropyrimidin-4(3H)-ones, Driven under the Umbrella of Sustainable
 Chemistry
;
_journal_issue                   10
_journal_name_full               'ACS Sustainable Chemistry &amp; Engineering'
_journal_page_first              13358
_journal_paper_doi               10.1021/acssuschemeng.8b03127
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C13 H13 Cl N2 O S'
_chemical_formula_sum            'C13 H13 Cl N2 O S'
_chemical_formula_weight         280.76
_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_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 101.545(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.9132(13)
_cell_length_b                   10.5411(5)
_cell_length_c                   10.4984(4)
_cell_measurement_reflns_used    5953
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.3560
_cell_measurement_theta_min      2.7890
_cell_volume                     2701.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.135
_diffrn_reflns_theta_min         2.553
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.426
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         6994
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0854
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0834P)^2^+6.7424P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2111
_refine_ls_wR_factor_ref         0.2210
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5554
_reflns_number_total             6994
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sc8b03127_si_005.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4517031
_oxdiff_exptl_absorpt_empirical_full_min 0.896
_oxdiff_exptl_absorpt_empirical_full_max 1.105
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelxl_version_number           2014/6
_shelx_res_checksum              14950
_shelx_hkl_checksum              29319