Efficient N-Arylation and N-Alkenylation of the Five DNA/RNA Nucleobases
Mikkel F. Jacobsen; Martin M. Knudsen; Kurt V. Gothelf; Journal of Organic Chemistry 71 (2006) 9183–9190; doi:10.1021/jo061694i

data_4022125
_publ_section_title
;
 Efficient N-Arylation and N-Alkenylation of the Five DNA/RNA
 Nucleobases
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9183
_journal_page_last               9190
_journal_paper_doi               10.1021/jo061694i
_journal_volume                  71
_journal_year                    2006
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C21 H24 I1 N5 O4'
_chemical_formula_sum            'C21 H24 I N5 O4'
_chemical_formula_weight         537.35
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2006-06-20T08:07:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 96.5590(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4196(3)
_cell_length_b                   11.3876(3)
_cell_length_c                   16.0345(4)
_cell_measurement_reflns_used    8127
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.25
_cell_measurement_theta_min      2.55
_cell_measurement_wavelength     0.71073
_cell_volume                     2252.91(10)
_computing_cell_refinement       'Saint+ (Bruker-Nonius, 2006)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2006)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2006)'
_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      100(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method       '\f-scans and \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            91448
_diffrn_reflns_theta_full        34
_diffrn_reflns_theta_max         36.32
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    1.458
_exptl_absorpt_correction_T_max  0.7896
_exptl_absorpt_correction_T_min  0.6688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.881
_refine_diff_density_min         -1.153
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         10329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.034
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0293P)^2^+0.8319P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0603
_refine_ls_wR_factor_ref         0.0631
_reflns_number_gt                8804
_reflns_number_total             10329
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061694isi20060815_013158.cif
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022125