Synthesis and Antisense Properties of Fluoro Cyclohexenyl Nucleic Acid (F-CeNA), a Nuclease Stable Mimic of 2'-Fluoro RNA
Punit P. Seth; Jinghua Yu; Ali Jazayeri; Pradeep S. Pallan; Charles R Allerson; Michael E. Østergaard; Fengwu Liu; Piet Herdewijn; Martin Egli; Eric E. Swayze; Journal of Organic Chemistry 77 (2012) 5074–5085; doi:10.1021/jo300594b

data_4027233
_publ_section_title
;
 Synthesis and Antisense Properties of Fluoro Cyclohexenyl Nucleic Acid
 (F-CeNA), a Nuclease Stable Mimic of 2'-Fluoro RNA
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5074
_journal_page_last               5085
_journal_paper_doi               10.1021/jo300594b
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C12 H15 F N2 O4'
_chemical_formula_weight         270.26
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_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                 95.392(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.0342(7)
_cell_length_b                   8.4347(3)
_cell_length_c                   6.9512(2)
_cell_measurement_reflns_used    3506
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      66.23
_cell_measurement_theta_min      4.43
_cell_volume                     1169.43(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3915
_diffrn_reflns_theta_full        55.00
_diffrn_reflns_theta_max         66.62
_diffrn_reflns_theta_min         4.43
_exptl_absorpt_coefficient_mu    1.077
_exptl_absorpt_correction_T_max  0.913
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.23(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         1802
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+0.4220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0645
_refine_ls_wR_factor_ref         0.0649
_reflns_number_gt                1771
_reflns_number_total             1802
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300594b_si_003.cif
_cod_data_source_block           isis11
_cod_database_code               4027233