Triazolyl Donor/Acceptor Chromophore Decorated Unnatural Nucleosides and Oligonucleotides with Duplex Stability Comparable to That of a Natural Adenine/Thymine Pair
Subhendu Sekhar Bag; Sangita Talukdar; Katsuhiko Matsumoto; Rajen Kundu; Journal of Organic Chemistry 78 (2013) 278–291; doi:10.1021/jo302033f

data_4027848
_publ_section_title
;
 Triazolyl Donor/Acceptor Chromophore Decorated Unnatural Nucleosides and
 Oligonucleotides with Duplex Stability Comparable to That of a Natural
 Adenine/Thymine Pair
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              278
_journal_page_last               291
_journal_paper_doi               10.1021/jo302033f
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         C21H19N3O3
_chemical_formula_sum            'C21 H19 N3 O3'
_chemical_formula_weight         361.39
_chemical_name_common            Nucleoside
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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            4
_cell_length_a                   10.054(3)
_cell_length_b                   12.268(3)
_cell_length_c                   14.045(3)
_cell_measurement_reflns_used    1833
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      16.78
_cell_measurement_theta_min      2.62
_cell_volume                     1732.3(8)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_sigmaI/netI    0.0886
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17216
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.000
_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^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1184
_reflns_number_gt                1789
_reflns_number_total             3116
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302033f_si_002.cif
_cod_data_source_block           SSBST_TPhenBDo
_cod_original_cell_volume        1732.4(7)
_cod_database_code               4027848