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_2100542
_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         '(C18 H13 O2 N8 Cl1),0.5(H2 O)'
_chemical_formula_sum            'C18 H14 Cl N8 O2.5'
_chemical_formula_weight         417.82
_chemical_name_systematic
;
N-(8-methyl-2-(2-furyl)-8H-pyrazolo(4,3-e)(1,2,4)triazolo(1,5-c)
pyrimidin-5-yl)N-(2-chloro phenyl)-urea hemihydrate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.2320(9)
_cell_angle_beta                 95.9060(10)
_cell_angle_gamma                100.5670(10)
_cell_formula_units_Z            4
_cell_length_a                   6.98250(10)
_cell_length_b                   15.7877(3)
_cell_length_c                   17.8780(4)
_cell_measurement_reflns_used    14447
_cell_measurement_temperature    295
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      3.37
_cell_volume                     1887.81(6)
_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 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14447
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.37
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.391
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     644
_refine_ls_number_reflns         8951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0603P)^2^+0.4454P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1381
_reflns_number_gt                6646
_reflns_number_total             8951
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            de5026.cif
_cod_data_source_block           compound1
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C18 H14 Cl1 N8 O2.5'
_cod_database_code               2100542