Four products from the cyanoacetylation of pyrimidines: hydrogen-bonded dimers, π-stacked hydrogen-bonded chains and hydrogen-bonded chains of edge-fused rings
Trilleras, Jorge; Low, John N.; Cobo, Justo; Marchal, Antonio; Glidewell, Christopher; Acta Crystallographica Section C 64 (2008) o149–o154; doi:10.1107/S0108270108003557

data_2016481
_publ_section_title
;
 Four products from the cyanoacetylation of pyrimidines:
 hydrogen-bonded dimers, \p-stacked hydrogen-bonded chains and
 hydrogen-bonded chains of edge-fused rings
;
_journal_coeditor_code           GA3078
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o149
_journal_page_last               o154
_journal_paper_doi               10.1107/S0108270108003557
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C8 H7 Cl N4 O S'
_chemical_formula_moiety         'C8 H7 Cl N4 O S'
_chemical_formula_sum            'C8 H7 Cl N4 O S'
_chemical_formula_weight         242.69
_chemical_name_systematic
;
2-cyano-<i>N</i>-[6-chloro-2-(methylsulfanyl)pyrimidin-4-yl]acetamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 108.827(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8655(7)
_cell_length_b                   8.4390(2)
_cell_length_c                   9.9327(15)
_cell_measurement_reflns_used    2336
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      3.24
_cell_volume                     1020.71(18)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg <i>et al.</i>,  2000)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg <i>et al.</i>,  2003)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement
'OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla <i>et al.</i>,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22495
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         3.24
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.555
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.644
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0606
_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^)+(0.0836P)^2^+2.4077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1476
_refine_ls_wR_factor_ref         0.1750
_reflns_number_gt                1676
_reflns_number_total             2336
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ga3078.cif
_cod_data_source_block           IV
_cod_original_cell_volume        1020.72(18)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2016481
_cod_database_fobs_code          2016481