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_7150909
_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_absolute_configuration ad
_chemical_formula_moiety         'C20 H23 N5 O1'
_chemical_formula_sum            'C20 H23 N5 O'
_chemical_formula_weight         349.44
_chemical_name_common
9-Benzyl-6-(2-(diethylcarbamoyl)cyclopropyl)purine
_chemical_name_systematic
9-Benzyl-6-[2-(diethylcarbamoyl)cyclopropyl]purine
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             08-02-07
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.2791(2)
_cell_length_b                   16.20300(10)
_cell_length_c                   4.98
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     1797.72(2)
_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 0.996
_diffrn_measured_fraction_theta_max 0.990
_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  0.032
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            26954
_diffrn_reflns_theta_full        74.396
_diffrn_reflns_theta_max         76.697
_diffrn_reflns_theta_min         3.968
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
Analytical Absorption (De Meulenaer & Tompa, 1965)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.12
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details 'Flack (1983), 1507 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       24(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0836
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2807
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.000574
_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:
2.28 1.47 0.608
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0402
_refine_ls_wR_factor_gt          0.0328
_refine_ls_wR_factor_ref         0.0328
_reflns_limit_h_max              27
_reflns_limit_h_min              0
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              6
_reflns_limit_l_min              -5
_reflns_number_gt                2807
_reflns_number_total             3604
_reflns_threshold_expression     I>2.0\s(I)
_cod_data_source_file            b802833h.txt
_cod_data_source_block           CRYSTALS1_cif
_cod_original_formula_sum        'C20 H23 N5 O1'
_cod_database_code               7150909