Substituted pyrazolo[3,4-b]pyridines as human A1 adenosine antagonists: Developments in understanding the receptor stereoselectivity
Tuccinardi, Tiziano; Zizzari, Alessandra Tania; Brullo, Chiara; Daniele, Simona; Musumeci, Francesca; Schenone, Silvia; Trincavelli, Maria Letizia; Martini, Claudia; Martinelli, Adriano; Giorgi, Gianluca; Botta, Maurizio; Organic & Biomolecular Chemistry 9 (2011) 4448–; doi:10.1039/c0ob01064b

data_7151811
_publ_section_title
;
 Substituted pyrazolo[3,4-b]pyridines as human A1 adenosine
 antagonists: Developments in understanding the receptor
 stereoselectivity
;
_journal_issue                   12
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              4448
_journal_paper_doi               10.1039/c0ob01064b
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C25 H25 Cl N4 O3'
_chemical_formula_sum            'C25 H25 Cl N4 O3'
_chemical_formula_weight         464.94
_chemical_name_systematic
;
1-((R)-2-chloro-2-phenylethyl)-5-(2-hydroxy-1-methoxyethyl)-N-
-(4-methoxyphenethyl)-1H-pyrazolo[3,4-b]pyridin-4-amine
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.5930(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   5.4217(2)
_cell_length_b                   20.2401(9)
_cell_length_c                   40.7250(17)
_cell_measurement_reflns_used    45898
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     4467.3(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1101
_diffrn_reflns_av_sigmaI/netI    0.1818
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            40945
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.15(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1197
_refine_ls_number_reflns         19200
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.2048
_refine_ls_R_factor_gt           0.1084
_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^)+(0.0000P)^2^+15.5803P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1798
_refine_ls_wR_factor_ref         0.2254
_reflns_number_gt                10310
_reflns_number_total             19200
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c0ob01064b.txt
_cod_data_source_block           2008acc1217
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7151811