Hydrogen bonding in nitroaniline analogues: a hydrogen-bonded chain of rings in 2-amino-4-butylamino-6-methoxy-5-nitropyrimidine
Glidewell, Christopher; Low, John N.; Melguizo, Manuel; Quesada, Antonio; Acta Crystallographica Section C 59 (2003) o19–o21; doi:10.1107/S0108270102020991

data_2013201
_publ_section_title
;
 Hydrogen bonding in nitroaniline analogues: a hydrogen-bonded chain of
 rings in 2-amino-4-butylamino-6-methoxy-5-nitropyrimidine
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o19
_journal_page_last               o21
_journal_paper_doi               10.1107/S0108270102020991
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C9 H15 N5 O3'
_chemical_formula_sum            'C9 H15 N5 O3'
_chemical_formula_weight         241.26
_chemical_name_systematic
;
2-Amino-4-butylamino-6-methoxy-5-nitropyrimidine
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 109.810(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.5825(13)
_cell_length_b                   8.8102(4)
_cell_length_c                   13.0289(11)
_cell_measurement_reflns_used    2482
_cell_measurement_temperature    120.0(10)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      3.22
_cell_volume                     2222.8(3)
_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      120.0(10)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.124
_diffrn_reflns_av_sigmaI/netI    0.102
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16040
_diffrn_reflns_theta_full        27.38
_diffrn_reflns_theta_max         27.38
_diffrn_reflns_theta_min         3.22
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO-SMN; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2482
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      0.931
_refine_ls_R_factor_all          0.170
_refine_ls_R_factor_gt           0.063
_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^)+(0.0759P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.127
_refine_ls_wR_factor_ref         0.163
_reflns_number_gt                1151
_reflns_number_total             2482
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk1600.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      'C 2/c'
_cod_database_code               2013201
_cod_database_fobs_code          2013201