Hydrogen bonding in nitroaniline analogues: hydrogen-bonded sheets in 2-amino-4,6-dimethoxy-5-nitropyrimidine and π-stacked hydrogen-bonded sheets in 4-amino-2,6-dimethoxy-5-nitropyrimidine
Glidewell, Christopher; Low, John N.; Melguizo, Manuel; Quesada, Antonio; Acta Crystallographica Section C 59 (2003) o14–o18; doi:10.1107/S0108270102020322

data_2013199
_publ_section_title
;
 Hydrogen bonding in nitroaniline analogues: hydrogen-bonded sheets in
 2-amino-4,6-dimethoxy-5-nitropyrimidine and \p-stacked hydrogen-bonded
 sheets in 4-amino-2,6-dimethoxy-5-nitropyrimidine
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o14
_journal_page_last               o18
_journal_paper_doi               10.1107/S0108270102020322
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C6 H8 N4 O4'
_chemical_formula_sum            'C6 H8 N4 O4'
_chemical_formula_weight         200.16
_chemical_name_systematic
;
2-Amino-4,6-dimethoxy-5-nitropyrimidine
;
_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
_cell_angle_beta                 109.9470(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3443(2)
_cell_length_b                   7.8437(2)
_cell_length_c                   14.9129(4)
_cell_measurement_reflns_used    1835
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.95
_cell_volume                     807.54(4)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_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           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_av_sigmaI/netI    0.048
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6065
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         2.95
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO-SMN; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.048
_refine_ls_R_factor_gt           0.040
_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^)+(0.0617P)^2^+0.2772P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.104
_refine_ls_wR_factor_ref         0.110
_reflns_number_gt                1569
_reflns_number_total             1835
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk1599.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2013199
_cod_database_fobs_code          2013199