Adjusting the Structure of 2'-Modified Nucleosides and Oligonucleotides via C4'-α-F or C4'-α-OMe Substitution: Synthesis and Conformational Analysis.
Malek-Adamian, Elise; Patrascu, Mihai Burai; Jana, Sunit Kumar; Martínez-Montero, Saúl; Moitessier, Nicolas; Damha, Masad J.; The Journal of organic chemistry 83 (2018) 9839–9849; doi:10.1021/acs.joc.8b01329

data_4035102
_publ_section_title
;
 Adjusting the Structure of 2'-Modified Nucleosides and Oligonucleotides
 via C4'-\a-F or C4'-\a-OMe Substitution: Synthesis and Conformational
 Analysis.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9839
_journal_page_last               9849
_journal_paper_doi               10.1021/acs.joc.8b01329
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C10 H13 F N2 O6, H2 O'
_chemical_formula_sum            'C10 H15 F N2 O7'
_chemical_formula_weight         294.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.9540(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.0065(15)
_cell_length_b                   6.5012(3)
_cell_length_c                   13.4207(7)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.647
_cell_measurement_theta_min      2.710
_cell_volume                     2476.1(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24248
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.615
_diffrn_reflns_theta_min         3.029
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    0.802
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0962 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.8840. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.128
_refine_ls_abs_structure_details
;
 Flack x determined using 2485 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_extinction_coef       0.0205(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         5593
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0747P)^2^+2.2968P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1285
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                5562
_reflns_number_total             5593
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01329_si_005.cif
_cod_data_source_block           damha25
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4035102
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.869
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O31-H31A \\sim O31-H31B \\sim O32-H32A \\sim O32-H32B
 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2B), C3(H3), C11(H11), C12(H12B), C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C17(H17), C18(H18)
3.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              94831
_shelx_hkl_checksum              17300
_olex2_submission_special_instructions 'No special instructions were received'