Synthesis of substituted 6-cyclopropylpurine bases and nucleosides by cross-coupling reactions or cyclopropanations
Kuchař, Martin; Pohl, Radek; Klepetářová, Blanka; Votruba, Ivan; Hocek, Michal; Organic & Biomolecular Chemistry 6 (2008) 2377–2387; doi:10.1039/b802833h

data_7150908
_publ_section_title
;
 Synthesis of substituted 6-cyclopropylpurine bases and nucleosides by
 cross-coupling reactions or cyclopropanations
;
_journal_issue                   13
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              2377
_journal_page_last               2387
_journal_paper_doi               10.1039/b802833h
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C8 H8 N4'
_chemical_formula_sum            'C8 H8 N4'
_chemical_formula_weight         160.18
_chemical_name_common            6-cyclopropyl-9H-purine
_chemical_name_systematic        6-cyclopropyl-9H-purine
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      12
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             08-02-06
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 99.789(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6246(3)
_cell_length_b                   7.01430(10)
_cell_length_c                   7.8922(2)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      6
_cell_volume                     743.25(3)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11926
_diffrn_reflns_theta_full        69.294
_diffrn_reflns_theta_max         76.147
_diffrn_reflns_theta_min         5.689
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
Analytical Absorption (De Meulenaer & Tompa, 1965)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.29
_refine_ls_extinction_coef       52(7)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9440
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         723
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.000275
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
15.4 2.45 13.6
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0588
_refine_ls_wR_factor_gt          0.0577
_refine_ls_wR_factor_ref         0.0577
_reflns_limit_h_max              16
_reflns_limit_h_min              -17
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                723
_reflns_number_total             820
_reflns_threshold_expression     I>2.0\s(I)
_cod_data_source_file            b802833h.txt
_cod_data_source_block           CRYSTALS_cif
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7150908