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_2100543
_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'
_chemical_formula_sum            'C22 H22 N8 O3'
_chemical_formula_weight         446.48
_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-(3-methoxyphenyl)-urea
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.9170(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2816(2)
_cell_length_b                   24.0888(5)
_cell_length_c                   8.1651(3)
_cell_measurement_reflns_used    9542
_cell_measurement_temperature    295
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.7
_cell_volume                     2153.81(10)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0851
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9542
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
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_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.07
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_refine_diff_density_min         -0.243
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         5159
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_refine_ls_R_factor_all          0.1458
_refine_ls_R_factor_gt           0.0598
_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^)+(0.0509P)^2^+0.3032P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1410
_reflns_number_gt                2594
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_reflns_threshold_expression     I>2sigma(I)
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_cod_database_code               2100543