Six closely related 4,6-disubstituted 2-amino-5-formylpyrimidines: different ring conformations, polarized electronic structures, and hydrogen-bonded assembly in zero, one, two and three dimensions
Acosta, Lina M.; Yepes, Andrés F.; Palma, Alirio; Cobo, Justo; Glidewell, Christopher; Acta Crystallographica Section C 69 (2013) 162–171; doi:10.1107/S0108270112051049

data_2018802
_publ_section_title
;
 Six closely related 4,6-disubstituted 2-amino-5-formylpyrimidines:
 different ring conformations, polarized electronic structures, and
 hydrogen-bonded assembly in zero, one, two and three dimensions
;
_journal_coeditor_code           YF3022
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              162
_journal_page_last               171
_journal_paper_doi               10.1107/S0108270112051049
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C16 H19 N5 O3'
_chemical_formula_moiety         'C16 H19 N5 O3'
_chemical_formula_sum            'C16 H19 N5 O3'
_chemical_formula_weight         329.36
_chemical_name_systematic
;
Ethyl
<i>N</i>-{2-amino-5-formyl-6-[methyl(phenyl)amino]pyrimidin-4-yl}glycinate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_cell_angle_alpha                73.30(2)
_cell_angle_beta                 82.680(14)
_cell_angle_gamma                72.693(13)
_cell_formula_units_Z            2
_cell_length_a                   7.3990(5)
_cell_length_b                   9.609(3)
_cell_length_c                   12.449(3)
_cell_measurement_reflns_used    3718
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.16
_cell_volume                     808.5(3)
_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, 2009)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla <i>et al.</i>, 2005)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_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  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18365
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.16
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.166
_refine_ls_extinction_coef       0.033(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0562P)^2^+0.2215P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                2054
_reflns_number_total             3006
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            yf3022.cif
_cod_data_source_block           I
_cod_database_code               2018802
_cod_database_fobs_code          2018802