Hydrogen bonding in 2-amino-4-methoxy-6-methylpyrimidine, 2-benzylamino-4-benzyloxy-6-methylpyrimidine and 4-benzylamino-2,6-bis(benzyloxy)pyrimidine: π-stacked chains of fused <i>R</i>~2~^2^(8) rings, and centrosymmetric <i>R</i>~2~^2^(8) dimers
Glidewell, Christopher; Low, John N.; Melguizo, Manuel; Quesada, Antonio; Acta Crystallographica Section C 59 (2003) o9–o13; doi:10.1107/S0108270102020206

data_2013183
_publ_section_title
;
 Hydrogen bonding in 2-amino-4-methoxy-6-methylpyrimidine,
 2-benzylamino-4-benzyloxy-6-methylpyrimidine and
 4-benzylamino-2,6-bis(benzyloxy)pyrimidine: \p-stacked chains of fused
 <i>R</i>~2~^2^(8) rings, and centrosymmetric <i>R</i>~2~^2^(8) dimers
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o9
_journal_page_last               o13
_journal_paper_doi               10.1107/S0108270102020206
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C19 H19 N3 O'
_chemical_formula_moiety         'C19 H19 N3 O'
_chemical_formula_sum            'C19 H19 N3 O'
_chemical_formula_weight         305.38
_chemical_name_systematic
;
2-Benzylamino-4-benzyloxy-6-methylpyrimidine
;
_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                 98.704(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8932(2)
_cell_length_b                   18.2849(7)
_cell_length_c                   15.1175(7)
_cell_measurement_reflns_used    3667
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.94
_cell_volume                     1610.25(11)
_computing_cell_refinement       'DENZO--SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction        DENZO--SMN
_computing_molecular_graphics    'PLATON (Spek, 2002)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\f scans, and \w scans with \k offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.093
_diffrn_reflns_av_sigmaI/netI    0.0734
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12340
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.94
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO-SMN; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.278
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0662P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                2371
_reflns_number_total             3667
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            na1584.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2013183
_cod_database_fobs_code          2013183