Triazole- and Tetrazole-Bridged Nucleic Acids: Synthesis, Duplex Stability, Nuclease Resistance, and in Vitro and in Vivo Antisense Potency.
Mitsuoka, Yasunori; Yamamoto, Tsuyoshi; Kugimiya, Akira; Waki, Reiko; Wada, Fumito; Tahara, Saori; Sawamura, Motoki; Noda, Mio; Fujimura, Yuko; Kato, Yuki; Hari, Yoshiyuki; Obika, Satoshi; The Journal of organic chemistry 82 (2017) 12–24; doi:10.1021/acs.joc.6b02417

data_4032104
_publ_section_title
;
 Triazole- and Tetrazole-Bridged Nucleic Acids: Synthesis, Duplex
 Stability, Nuclease Resistance, and in Vitro and in Vivo Antisense
 Potency.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12
_journal_page_last               24
_journal_paper_doi               10.1021/acs.joc.6b02417
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C12 H13 N5 O5, H2 O'
_chemical_formula_sum            'C12 H15 N5 O6'
_chemical_formula_weight         325.29
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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                   6.56614(12)
_cell_length_b                   12.6523(2)
_cell_length_c                   16.1928(3)
_cell_measurement_reflns_used    12050
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      3.50
_cell_volume                     1345.25(4)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, 2010)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0111
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15873
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         4.43
_exptl_absorpt_coefficient_mu    1.123
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2446
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0269
_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^)+(0.0327P)^2^+0.6019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0678
_reflns_number_gt                2383
_reflns_number_total             2446
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02417_si_002.cif
_cod_data_source_block           TrNA-T(8)
_cod_depositor_comments
'Adding full bibliography for 4032104--4032105.cif.'
_cod_original_cell_volume        1345.24(4)
_cod_database_code               4032104
_shelx_hkl_checksum              14354