Fluorinated enamines of nucleobases as precursors of nucleoside analogues. Synthesis, spectroscopic and structural studies
Wójtowicz-Rajchel, Hanna; Pasikowska, Magda; Olejniczak, Anna; Katrusiak, Andrzej; Koroniak, Henryk; New Journal of Chemistry 34 (2010) 894–; doi:10.1039/b9nj00617f

data_7053391
_publ_section_title
;
 Fluorinated enamines of nucleobases as precursors of nucleoside
 analogues. Synthesis, spectroscopic and structural studies
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              894
_journal_paper_doi               10.1039/b9nj00617f
_journal_volume                  34
_journal_year                    2010
_chemical_formula_moiety         'C14 H9 F4 N3 O2 '
_chemical_formula_sum            'C14 H9 F4 N3 O2'
_chemical_formula_weight         327.24
_chemical_name_common
;
N-(2-oxo-1-((1Z)-1,3,3,3-tetrafluoroprop-1-en-1-yl) -1,2-
dihydropyrimidin-4-yl)benzamide
;
_chemical_name_systematic
;
N-{2-oxo-1-[(1Z)-1,3,3,3-tetrafluoroprop-1-en-1-yl]
-1,2-dihydropyrimidin-4-yl}benzamide
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 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                 105.596(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.050(2)
_cell_length_b                   12.1206(19)
_cell_length_c                   15.425(2)
_cell_measurement_reflns_used    17292
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.28
_cell_measurement_theta_min      2.74
_cell_volume                     2710.2(7)
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_molecular_graphics
;X-Seed (Barbour, 2001)
and POV-Ray (Persistence of Vision, 2004)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.912
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  'Kuma KM4CCD \k geometry'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17292
_diffrn_reflns_theta_full        29.28
_diffrn_reflns_theta_max         29.28
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.750
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_coef       0.0027(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     874
_refine_ls_number_reflns         8467
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0822
_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^)+(0.1784P)^2^+1.0769P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2454
_refine_ls_wR_factor_ref         0.2706
_reflns_number_gt                6499
_reflns_number_total             8467
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b9nj00617f.txt
_cod_data_source_block           C14H9F4N3O2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2710.1(7)
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               7053391