#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/61/2226182.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226182
loop_
_publ_author_name
'Mendoza, Angel'
'Sosa-Rivadeneyra, Martha'
'Sartillo-Piscil, Fernando'
'Quintero, Leticia'
'Flores-Alamo, Marcos'
_publ_section_title
;
 5-Fluoro-1-[(4S,5R)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]pyrimidine-2,4(1H,3H)-dione
;
_journal_coeditor_code           IS2543
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1317
_journal_paper_doi               10.1107/S1600536810016065
_journal_volume                  66
_journal_year                    2010
_chemical_formula_moiety         'C11 H15 F N2 O5'
_chemical_formula_sum            'C11 H15 F N2 O5'
_chemical_formula_weight         274.25
_chemical_name_common
;
5-Fluoro-1-[(1S,2R)-4-hydroxy-1,2-O-
isopropylidenebutyl]uracil
;
_chemical_name_systematic
;
5-Fluoro-1-[(4S,5R)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-
dioxolan-4-yl]pyrimidine-2,4(1H,3H)-dione
;
_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                 126.297(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.8905(8)
_cell_length_b                   5.57510(10)
_cell_length_c                   13.5639(5)
_cell_measurement_reflns_used    4215
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      67.9856
_cell_measurement_theta_min      4.0405
_cell_volume                     1273.21(12)
_computing_cell_refinement
'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_data_collection
'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Oxford Diffraction Gemini Atlas CCD diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0128
_diffrn_reflns_av_sigmaI/netI    0.0089
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4606
_diffrn_reflns_theta_full        68.10
_diffrn_reflns_theta_max         68.10
_diffrn_reflns_theta_min         4.04
_diffrn_standards_number         4614
_exptl_absorpt_coefficient_mu    1.056
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.3956
_exptl_crystal_size_mid          0.1147
_exptl_crystal_size_min          0.0770
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.195
_refine_ls_abs_structure_details 'Flack (1983), 498 Friedel pairs'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.0075(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1786
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0274
_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/[σ²(Fo²)+(0.0380P)²+0.4768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0711
_reflns_number_gt                1732
_reflns_number_total             1786
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2543.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2226182
_cod_database_fobs_code          2226182
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.69200(8) 0.0051(3) 0.95722(12) 0.0519(4) Uani d . 1 . .
N N1 0.66380(8) 0.2920(3) 0.81679(12) 0.0339(3) Uani d . 1 . .
O O4 0.72382(7) 0.3751(3) 0.65042(11) 0.0438(3) Uani d . 1 . .
F F1 0.52029(9) 0.7673(3) 0.69645(15) 0.0816(5) Uani d . 1 . .
O O5 0.90402(9) 0.7069(3) 0.88915(13) 0.0478(4) Uani d . 1 . .
O O2 0.49424(9) 0.5250(3) 0.84757(15) 0.0627(5) Uani d . 1 . .
C C5 0.72230(11) 0.1894(4) 0.80156(17) 0.0403(4) Uani d . 1 . .
H H5 0.7609 0.0950 0.8745 0.048 Uiso calc R 1 . .
N N2 0.59707(9) 0.2801(4) 0.90550(15) 0.0434(4) Uani d . 1 . .
C C1 0.61955(10) 0.4901(4) 0.75175(16) 0.0418(4) Uani d . 1 . .
H H1 0.6291 0.5673 0.7009 0.050 Uiso calc R 1 . .
O O3 0.68552(11) 0.0402(3) 0.69943(16) 0.0681(5) Uani d . 1 . .
C C4 0.65428(10) 0.1784(4) 0.89752(15) 0.0362(4) Uani d . 1 . .
C C6 0.76688(9) 0.3754(4) 0.78102(14) 0.0350(4) Uani d . 1 . .
H H6 0.7625 0.5332 0.8084 0.042 Uiso calc R 1 . .
C C2 0.56349(11) 0.5732(4) 0.76007(18) 0.0466(5) Uani d . 1 . .
C C3 0.54650(10) 0.4653(4) 0.83818(17) 0.0435(5) Uani d . 1 . .
C C8 0.89973(11) 0.4915(4) 0.83002(18) 0.0469(5) Uani d . 1 . .
H H8A 0.9528 0.4318 0.8649 0.056 Uiso calc R 1 . .
H H8B 0.8733 0.5206 0.7435 0.056 Uiso calc R 1 . .
C C7 0.85368(10) 0.3099(4) 0.84748(17) 0.0437(5) Uani d . 1 . .
H H7A 0.8779 0.2948 0.9342 0.052 Uiso calc R 1 . .
H H7B 0.8572 0.1551 0.8184 0.052 Uiso calc R 1 . .
C C9 0.68429(13) 0.1521(4) 0.60232(19) 0.0533(6) Uani d . 1 . .
C C10 0.72705(17) -0.0147(5) 0.5721(2) 0.0689(7) Uani d . 1 . .
H H10A 0.6979 -0.1621 0.5400 0.103 Uiso calc R 1 . .
H H10B 0.7793 -0.0473 0.6448 0.103 Uiso calc R 1 . .
H H10C 0.7313 0.0588 0.5121 0.103 Uiso calc R 1 . .
C C11 0.60061(17) 0.2034(8) 0.4934(3) 0.1094(13) Uani d . 1 . .
H H11A 0.5725 0.0550 0.4592 0.164 Uiso calc R 1 . .
H H11B 0.6016 0.2893 0.4330 0.164 Uiso calc R 1 . .
H H11C 0.5743 0.2986 0.5185 0.164 Uiso calc R 1 . .
H H1N 0.5950(12) 0.236(5) 0.9622(19) 0.048(6) Uiso d . 1 . .
H H1O 0.9348(15) 0.789(6) 0.896(2) 0.072(9) Uiso d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C4 . . 121.43(14) ?
C1 N1 C5 . . 121.47(14) ?
C4 N1 C5 . . 117.10(15) ?
C9 O4 C6 . . 109.72(14) ?
C8 O5 H1O . . 110(2) ?
O3 C5 N1 . . 110.92(16) ?
O3 C5 C6 . . 105.14(14) ?
N1 C5 C6 . . 114.14(16) ?
O3 C5 H5 . . 108.8 ?
N1 C5 H5 . . 108.8 ?
C6 C5 H5 . . 108.8 ?
C3 N2 C4 . . 128.17(16) ?
C3 N2 H1N . . 113.4(16) ?
C4 N2 H1N . . 118.1(16) ?
C2 C1 N1 . . 121.28(17) ?
C2 C1 H1 . . 119.4 ?
N1 C1 H1 . . 119.4 ?
C5 O3 C9 . . 110.51(16) ?
O1 C4 N1 . . 123.91(16) ?
O1 C4 N2 . . 121.80(16) ?
N1 C4 N2 . . 114.29(16) ?
O4 C6 C7 . . 112.88(14) ?
O4 C6 C5 . . 102.72(13) ?
C7 C6 C5 . . 111.86(15) ?
O4 C6 H6 . . 109.7 ?
C7 C6 H6 . . 109.7 ?
C5 C6 H6 . . 109.7 ?
C1 C2 F1 . . 121.20(18) ?
C1 C2 C3 . . 122.28(19) ?
F1 C2 C3 . . 116.51(17) ?
O2 C3 N2 . . 121.46(18) ?
O2 C3 C2 . . 126.3(2) ?
N2 C3 C2 . . 112.25(16) ?
O5 C8 C7 . . 108.20(15) ?
O5 C8 H8A . . 110.1 ?
C7 C8 H8A . . 110.1 ?
O5 C8 H8B . . 110.1 ?
C7 C8 H8B . . 110.1 ?
H8A C8 H8B . . 108.4 ?
C8 C7 C6 . . 113.23(17) ?
C8 C7 H7A . . 108.9 ?
C6 C7 H7A . . 108.9 ?
C8 C7 H7B . . 108.9 ?
C6 C7 H7B . . 108.9 ?
H7A C7 H7B . . 107.7 ?
O4 C9 O3 . . 105.54(16) ?
O4 C9 C11 . . 107.9(2) ?
O3 C9 C11 . . 111.2(2) ?
O4 C9 C10 . . 112.88(19) ?
O3 C9 C10 . . 106.8(2) ?
C11 C9 C10 . . 112.5(2) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C9 C11 H11A . . 109.5 ?
C9 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C9 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.206(2) ?
N1 C1 . 1.373(3) ?
N1 C4 . 1.378(2) ?
N1 C5 . 1.471(2) ?
O4 C9 . 1.419(3) ?
O4 C6 . 1.435(2) ?
F1 C2 . 1.345(2) ?
O5 C8 . 1.417(3) ?
O5 H1O . 0.75(3) ?
O2 C3 . 1.218(2) ?
C5 O3 . 1.393(3) ?
C5 C6 . 1.526(3) ?
C5 H5 . 0.9800 ?
N2 C3 . 1.369(3) ?
N2 C4 . 1.384(2) ?
N2 H1N . 0.83(2) ?
C1 C2 . 1.325(3) ?
C1 H1 . 0.9300 ?
O3 C9 . 1.444(3) ?
C6 C7 . 1.516(2) ?
C6 H6 . 0.9800 ?
C2 C3 . 1.434(3) ?
C8 C7 . 1.509(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C9 C11 . 1.504(4) ?
C9 C10 . 1.505(3) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H1N O5 4_647 0.83(2) 2.01(2) 2.828(2) 167(3)
O5 H1O O2 3 0.75(3) 2.16(3) 2.876(2) 160(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 C5 O3 . . . . -82.0(2) ?
C4 N1 C5 O3 . . . . 96.83(19) ?
C1 N1 C5 C6 . . . . 36.5(2) ?
C4 N1 C5 C6 . . . . -144.63(16) ?
C4 N1 C1 C2 . . . . -3.0(3) ?
C5 N1 C1 C2 . . . . 175.8(2) ?
N1 C5 O3 C9 . . . . 107.78(18) ?
C6 C5 O3 C9 . . . . -16.1(2) ?
C1 N1 C4 O1 . . . . -179.53(18) ?
C5 N1 C4 O1 . . . . 1.6(3) ?
C1 N1 C4 N2 . . . . 0.4(3) ?
C5 N1 C4 N2 . . . . -178.50(15) ?
C3 N2 C4 O1 . . . . -175.3(2) ?
C3 N2 C4 N1 . . . . 4.8(3) ?
C9 O4 C6 C7 . . . . 96.42(19) ?
C9 O4 C6 C5 . . . . -24.21(19) ?
O3 C5 C6 O4 . . . . 24.16(19) ?
N1 C5 C6 O4 . . . . -97.61(16) ?
O3 C5 C6 C7 . . . . -97.17(18) ?
N1 C5 C6 C7 . . . . 141.06(16) ?
N1 C1 C2 F1 . . . . 179.91(19) ?
N1 C1 C2 C3 . . . . 1.0(3) ?
C4 N2 C3 O2 . . . . 173.9(2) ?
C4 N2 C3 C2 . . . . -6.5(3) ?
C1 C2 C3 O2 . . . . -177.1(2) ?
F1 C2 C3 O2 . . . . 4.0(3) ?
C1 C2 C3 N2 . . . . 3.3(3) ?
F1 C2 C3 N2 . . . . -175.64(18) ?
O5 C8 C7 C6 . . . . 67.2(2) ?
O4 C6 C7 C8 . . . . 65.3(2) ?
C5 C6 C7 C8 . . . . -179.47(16) ?
C6 O4 C9 O3 . . . . 15.2(2) ?
C6 O4 C9 C11 . . . . 134.1(2) ?
C6 O4 C9 C10 . . . . -101.1(2) ?
C5 O3 C9 O4 . . . . 1.4(2) ?
C5 O3 C9 C11 . . . . -115.3(2) ?
C5 O3 C9 C10 . . . . 121.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745015
