Synthesis of fluorinated carbocyclic pyrimidine nucleoside analogues
Benckendorff, Caecilie M. M.; Slyusarchuk, Valentyna; Huang, Ningwu; Lima, Marcelo A.; Smith, Mark; Miller, Gavin John; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01761J

data_7158991
_publ_section_title
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 Synthesis of fluorinated carbocyclic pyrimidine nucleoside analogues
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_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01761J
_journal_year                    2022
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C10 H15 F O3'
_chemical_formula_sum            'C10 H15 F O3'
_chemical_formula_weight         202.22
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-19
_audit_creation_method
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Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
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_audit_update_record
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2022-07-27 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   11.884(3)
_cell_length_b                   11.884(3)
_cell_length_c                   6.298(2)
_cell_measurement_reflns_used    3645
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      25.298
_cell_measurement_theta_min      3.429
_cell_volume                     770.3(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0742
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15475
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.522
_diffrn_reflns_theta_min         3.429
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0645 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.9256.
The \l/2 correction factor is Not present.
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_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 767 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         3119
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0296P)^2^+0.0876P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0896
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2179
_reflns_number_total             3119
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01761j2.cif
_cod_data_source_block           8
_cod_original_cell_volume        770.2(4)
_cod_database_code               7158991
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
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1. Others
 Fixed Uiso: H2(0.025) H3(0.023) H4(0.025) H5(0.03) H6(0.038) H7A(0.056)
 H7B(0.056) H1(0.069) H1A(0.029) H10A(0.051) H10B(0.051) H10C(0.051) H9A(0.048)
 H9B(0.048) H9C(0.048)
 Fixed X: H2(-0.008215) H3(0.133916) H4(0.268729) H5(0.276467) H6(0.079506)
 H7A(0.153134) H7B(0.057262) H1A(0.049649) H10A(0.35579) H10B(0.413731)
 H10C(0.504266) H9A(0.54954) H9B(0.453169) H9C(0.428743)
 Fixed Y: H2(0.212486) H3(0.182417) H4(0.402198) H5(0.508008) H6(0.51265)
 H7A(0.466891) H7B(0.526648) H1A(0.343358) H10A(0.248236) H10B(0.164586)
 H10C(0.31839) H9A(0.331502) H9B(0.178332) H9C(0.277647)
 Fixed Z: H2(0.424265) H3(0.226254) H4(0.203132) H5(0.578672) H6(0.476395)
 H7A(0.086989) H7B(0.136174) H1A(0.715272) H10A(0.101075) H10B(0.203271)
 H10C(0.176164) H9A(0.579264) H9B(0.602093) H9C(0.7388)
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_shelx_res_checksum              45998
_olex2_submission_special_instructions 'No special instructions were received'