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_7158993
_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         'C9 H14 F2 O4'
_chemical_formula_sum            'C9 H14 F2 O4'
_chemical_formula_weight         224.20
_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                   12.3659(5)
_cell_length_b                   12.3659(5)
_cell_length_c                   5.8839(4)
_cell_measurement_reflns_used    4123
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      3.295
_cell_volume                     779.20(7)
_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  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0334
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9224
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         3.295
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6801
_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 0.0533 before and 0.0490 after correction.
The Ratio of minimum to maximum transmission is 0.9122.
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    1.433
_exptl_crystal_description       plate
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 928 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2375
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0359P)^2^+0.0750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0714
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2110
_reflns_number_total             2375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01761j2.cif
_cod_data_source_block           16
_cod_original_cell_volume        779.20(8)
_cod_database_code               7158993
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.959
_olex2_refinement_description
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1. Others
 Fixed Uiso: H2(0.025) H3(0.026) H4A(0.027) H5(0.024) H6A(0.027) H6B(0.027)
 H9A(0.061) H9B(0.061) H9C(0.061) H1(0.061) H4(0.061) H8A(0.069) H8B(0.069)
 H8C(0.069)
 Fixed X: H2(0.4707) H3(0.6524) H4A(0.5232) H5(0.4245) H6A(0.3105) H6B(0.233)
 H9A(0.9218) H9B(0.8592) H9C(0.8324) H8A(0.6806) H8B(0.7747) H8C(0.8264)
 Fixed Y: H2(0.3336) H3(0.5086) H4A(0.5909) H5(0.5747) H6A(0.4148) H6B(0.4161)
 H9A(0.7897) H9B(0.8678) H9C(0.7427) H8A(0.707) H8B(0.8445) H8C(0.7536)
 Fixed Z: H2(0.2948) H3(0.1823) H4A(0.1483) H5(0.5733) H6A(0.1858) H6B(0.4032)
 H9A(0.4085) H9B(0.3189) H9C(0.1907) H8A(0.8182) H8B(0.7262) H8C(0.7961)
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_shelx_res_checksum              56568
_olex2_submission_special_instructions 'No special instructions were received'