Role of strong intramolecular N—H···N hydrogen bonds in determining the conformation of adenosine-receptor antagonists
V. Ferretti; L. Pretto; M. A. Tabrizi; P. Gilli; Acta Crystallographica Section B 62 (2006) 634–641; doi:10.1107/S0108768106013966

data_2100544
_publ_section_title
;
 Role of strong intramolecular N---H&#x00B7;&#x00B7;&#x00B7;N hydrogen
 bonds in determining the conformation of adenosine-receptor
 antagonists
;
_journal_coeditor_code           DE5026
_journal_date_accepted           2006-04-18
_journal_date_recd_electronic    2006-01-20
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              634
_journal_page_last               641
_journal_paper_category          FA
_journal_paper_doi               10.1107/S0108768106013966
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         '(C22 H22 N8 O3), 0.5(C4 H8 O2)'
_chemical_formula_sum            'C26 H30 N8 O5'
_chemical_formula_weight         490.53
_chemical_name_systematic
;
N-[8-butyl-2-(2-furyl)-8H-pyrazolo[4,3-e][1,2,4]
triazolo[1,5-c]pyrimidin-5-yl]N-(2-methoxyphenyl)urea
0.5 dioxane solvate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.8670(7)
_cell_angle_beta                 71.3280(7)
_cell_angle_gamma                70.6350(9)
_cell_formula_units_Z            4
_cell_length_a                   12.6218(2)
_cell_length_b                   14.0932(3)
_cell_length_c                   15.6948(4)
_cell_measurement_reflns_used    15610
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      2.0
_cell_volume                     2439.15(9)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Kappa CCD server software (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPIII(Burnett & Johnson, 1996)'
_computing_publication_material
;
SHELXL-97 (Sheldrick, 1997); PARST (Nardelli, 1983, 1995);
WINGX (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Nonius Kappa CCD'
_diffrn_measurement_method       '\f scans and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0518
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15610
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.199
_refine_ls_extinction_coef       0.054(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     889
_refine_ls_number_reflns         10558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0609
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0836P)^2^+0.5314P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1480
_refine_ls_wR_factor_ref         0.1829
_reflns_number_gt                6467
_reflns_number_total             10558
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            de5026.cif
_cod_data_source_block           compound3
_cod_original_cell_volume        2439.16(9)
_cod_database_code               2100544