Structure and Synthesis of 6-(Substituted-imidazol-1-yl)purines: Versatile Substrates for Regiospecific Alkylation and Glycosylation at N9
Minghong Zhong; Ireneusz Nowak; John F. Cannon; Morris J. Robins; Journal of Organic Chemistry 71 (2006) 4216–4221; doi:10.1021/jo060340o

data_4021705
_publ_contact_author_address
;Department of Chemistry and Biochemistry
Brigham Young University
Provo, Utah 84602-5700
USA
;
_publ_contact_author_email       morris_robins@byu.edu
_publ_contact_author_fax         '01 (801) 4220153'
_publ_contact_author_name        'Morris J. Robins'
_publ_contact_author_phone       '01 (801) 4226272'
_publ_section_title
;
 Structure and Synthesis of 6-(Substituted-imidazol-1-yl)purines:
 Versatile Substrates for Regiospecific Alkylation and
 Glycosylation at N9
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4216
_journal_page_last               4221
_journal_paper_doi               10.1021/jo060340o
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration unk
_chemical_formula_sum            'C15 H16 N6 O5'
_chemical_formula_weight         360.34
_chemical_name_systematic
; 
 9-(5-O-acetyl-\b-D-ribofuranosyl)-6-(imidazol-1-yl)purine 
;
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.6769(8)
_cell_length_b                   14.8384(14)
_cell_length_c                   25.297(2)
_cell_measurement_reflns_used    8335
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      2.72
_cell_volume                     3257.0(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Nonius Apex II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Montel 200 mirrors'
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0171
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19050
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_correction_T_min  0.9602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2003'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+1.2120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0782
_reflns_number_gt                3283
_reflns_number_total             3328
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060340osi20060222_024704.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4021705