#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/74/2017405.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_2017405
loop_
_publ_author_name
'Tutughamiarso, Maya'
'Bolte, Michael'
'Egert, Ernst'
_publ_section_title
;
 New pseudopolymorphs of 5-fluorocytosine
;
_journal_coeditor_code           SK3347
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o574
_journal_page_last               o578
_journal_paper_doi               10.1107/S010827010903950X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C4 H4 F N3 O , 0.5H2 O'
_chemical_formula_moiety         'C4 H4 F N3 O , 0.5H2 O'
_chemical_formula_sum            'C4 H5 F N3 O1.5'
_chemical_formula_weight         138.11
_chemical_name_systematic
;
5-fluorocytosine hemihydrate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.474(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   14.7039(13)
_cell_length_b                   12.4546(10)
_cell_length_c                   13.7921(14)
_cell_measurement_reflns_used    2945
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.76
_cell_measurement_theta_min      3.38
_cell_volume                     2280.2(4)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics
;
Mercury (Version 2.2; Macrae et al.,  2008) and XP (Sheldrick,
2008)
;
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       ω
_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  0.1041
_diffrn_reflns_av_sigmaI/netI    0.0662
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14246
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.666
_diffrn_reflns_theta_min         3.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.323
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.875
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         2141
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.873
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0375
_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)+(0.0397P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0779
_reflns_number_gt                1631
_reflns_number_total             2141
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3347.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'C c'
_cod_original_formula_sum        'C4 H5 F1 N3 O1.5'
_cod_database_code               2017405
_cod_database_fobs_code          2017405
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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
N N1A 0.7211(3) 0.6651(3) 0.5596(3) 0.0215(8) Uani d . 1 . .
H H1A 0.7418 0.7315 0.5602 0.026 Uiso calc R 1 . .
C C2A 0.6239(3) 0.6470(3) 0.5445(3) 0.0204(10) Uani d . 1 . .
N N3A 0.5915(3) 0.5442(3) 0.5449(3) 0.0204(8) Uani d . 1 . .
C C4A 0.6545(3) 0.4629(4) 0.5575(3) 0.0193(10) Uani d . 1 . .
C C5A 0.7542(3) 0.4821(4) 0.5719(4) 0.0232(10) Uani d . 1 . .
C C6A 0.7862(3) 0.5826(4) 0.5737(3) 0.0245(10) Uani d . 1 . .
H H6A 0.8535 0.5963 0.5847 0.029 Uiso calc R 1 . .
O O21A 0.5662(2) 0.7255(2) 0.5311(3) 0.0263(8) Uani d . 1 . .
N N41A 0.6204(3) 0.3632(3) 0.5544(3) 0.0262(9) Uani d . 1 . .
H H41A 0.5578 0.3524 0.5442 0.031 Uiso calc R 1 . .
H H41B 0.6605 0.3081 0.5625 0.031 Uiso calc R 1 . .
F F51A 0.8156(2) 0.3962(2) 0.5869(2) 0.0375(7) Uani d . 1 . .
N N1B 0.3981(3) 0.5036(3) 0.5387(3) 0.0202(8) Uani d . 1 . .
H H1B 0.4572 0.5148 0.5389 0.024 Uiso calc R 1 . .
C C2B 0.3681(3) 0.4000(3) 0.5427(3) 0.0179(9) Uani d . 1 . .
N N3B 0.2762(3) 0.3810(3) 0.5405(3) 0.0185(8) Uani d . 1 . .
C C4B 0.2158(3) 0.4628(4) 0.5338(3) 0.0199(10) Uani d . 1 . .
C C5B 0.2488(3) 0.5692(4) 0.5322(3) 0.0216(10) Uani d . 1 . .
C C6B 0.3397(3) 0.5890(4) 0.5344(3) 0.0210(10) Uani d . 1 . .
H H6B 0.3619 0.6604 0.5330 0.025 Uiso calc R 1 . .
O O21B 0.4265(2) 0.3249(2) 0.5486(3) 0.0258(7) Uani d . 1 . .
N N41B 0.1242(3) 0.4449(3) 0.5280(3) 0.0249(9) Uani d . 1 . .
H H41C 0.1036 0.3787 0.5286 0.030 Uiso calc R 1 . .
H H41D 0.0844 0.4993 0.5235 0.030 Uiso calc R 1 . .
F F51B 0.1859(2) 0.6524(2) 0.5265(2) 0.0332(7) Uani d . 1 . .
N N1C 0.6303(3) 0.3450(3) 0.7936(3) 0.0227(9) Uani d . 1 . .
H H1C 0.6110 0.4105 0.7995 0.027 Uiso calc R 1 . .
C C2C 0.7256(3) 0.3297(3) 0.8011(3) 0.0190(9) Uani d . 1 . .
N N3C 0.7559(3) 0.2280(3) 0.7933(3) 0.0195(8) Uani d . 1 . .
C C4C 0.6945(3) 0.1450(4) 0.7797(3) 0.0188(9) Uani d . 1 . .
C C5C 0.5955(3) 0.1631(4) 0.7710(4) 0.0254(11) Uani d . 1 . .
C C6C 0.5644(3) 0.2621(4) 0.7771(3) 0.0231(10) Uani d . 1 . .
H H6C 0.4982 0.2749 0.7703 0.028 Uiso calc R 1 . .
O O21C 0.7820(2) 0.4093(2) 0.8153(2) 0.0271(7) Uani d . 1 . .
N N41C 0.7259(3) 0.0468(3) 0.7751(3) 0.0252(9) Uani d . 1 . .
H H41E 0.7872 0.0363 0.7810 0.030 Uiso calc R 1 . .
H H41F 0.6855 -0.0082 0.7661 0.030 Uiso calc R 1 . .
F F51C 0.5349(2) 0.0759(2) 0.7559(2) 0.0350(7) Uani d . 1 . .
N N1D 0.9455(3) 0.1854(3) 0.7892(3) 0.0206(8) Uani d . 1 . .
H H1D 0.8864 0.1970 0.7890 0.025 Uiso calc R 1 . .
C C2D 0.9780(3) 0.0815(3) 0.7928(3) 0.0199(10) Uani d . 1 . .
N N3D 1.0713(3) 0.0633(3) 0.7972(3) 0.0196(8) Uani d . 1 . .
C C4D 1.1291(3) 0.1473(4) 0.7975(3) 0.0189(9) Uani d . 1 . .
C C5D 1.0911(3) 0.2535(4) 0.7884(4) 0.0249(11) Uani d . 1 . .
C C6D 1.0015(3) 0.2710(4) 0.7860(4) 0.0247(10) Uani d . 1 . .
H H6D 0.9767 0.3421 0.7820 0.030 Uiso calc R 1 . .
O O21D 0.9219(2) 0.0058(3) 0.7924(3) 0.0259(7) Uani d . 1 . .
N N41D 1.2219(3) 0.1290(3) 0.8066(3) 0.0233(9) Uani d . 1 . .
H H41G 1.2445 0.0627 0.8122 0.028 Uiso calc R 1 . .
H H41H 1.2605 0.1831 0.8069 0.028 Uiso calc R 1 . .
F F51D 1.1519(2) 0.3343(2) 0.7862(2) 0.0371(7) Uani d . 1 . .
O O1W 0.9690(2) 0.3874(3) 0.9907(3) 0.0337(8) Uani d D 1 . .
H H1WA 0.970(4) 0.324(2) 1.018(3) 0.040 Uiso d D 1 . .
H H1WB 0.918(3) 0.390(4) 0.924(2) 0.040 Uiso d D 1 . .
O O2W 0.3804(2) 0.7076(3) 0.3471(3) 0.0314(8) Uani d D 1 . .
H H2WA 0.433(3) 0.712(4) 0.412(2) 0.038 Uiso d D 1 . .
H H2WB 0.387(4) 0.648(3) 0.317(3) 0.038 Uiso d 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 0.0033 0.0016 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C6A N1A C2A . . 121.4(4) ?
C6A N1A H1A . . 119.3 ?
C2A N1A H1A . . 119.3 ?
O21A C2A N3A . . 121.0(4) ?
O21A C2A N1A . . 119.2(4) ?
N3A C2A N1A . . 119.8(4) ?
C4A N3A C2A . . 119.2(4) ?
N3A C4A N41A . . 118.3(4) ?
N3A C4A C5A . . 120.7(4) ?
N41A C4A C5A . . 121.0(4) ?
C6A C5A F51A . . 122.1(4) ?
C6A C5A C4A . . 119.8(4) ?
F51A C5A C4A . . 118.1(4) ?
C5A C6A N1A . . 119.1(4) ?
C5A C6A H6A . . 120.5 ?
N1A C6A H6A . . 120.5 ?
C4A N41A H41A . . 120.0 ?
C4A N41A H41B . . 120.0 ?
H41A N41A H41B . . 120.0 ?
C6B N1B C2B . . 122.2(4) ?
C6B N1B H1B . . 118.9 ?
C2B N1B H1B . . 118.9 ?
O21B C2B N3B . . 121.3(4) ?
O21B C2B N1B . . 118.9(4) ?
N3B C2B N1B . . 119.8(4) ?
C4B N3B C2B . . 119.7(4) ?
N3B C4B N41B . . 120.3(4) ?
N3B C4B C5B . . 119.7(4) ?
N41B C4B C5B . . 120.0(4) ?
C6B C5B F51B . . 120.2(4) ?
C6B C5B C4B . . 121.0(4) ?
F51B C5B C4B . . 118.8(4) ?
C5B C6B N1B . . 117.5(4) ?
C5B C6B H6B . . 121.3 ?
N1B C6B H6B . . 121.3 ?
C4B N41B H41C . . 120.0 ?
C4B N41B H41D . . 120.0 ?
H41C N41B H41D . . 120.0 ?
C6C N1C C2C . . 122.4(4) ?
C6C N1C H1C . . 118.8 ?
C2C N1C H1C . . 118.8 ?
O21C C2C N3C . . 122.1(4) ?
O21C C2C N1C . . 119.2(4) ?
N3C C2C N1C . . 118.7(4) ?
C4C N3C C2C . . 120.5(4) ?
N41C C4C N3C . . 119.8(4) ?
N41C C4C C5C . . 120.5(4) ?
N3C C4C C5C . . 119.7(4) ?
C6C C5C F51C . . 121.9(4) ?
C6C C5C C4C . . 120.4(4) ?
F51C C5C C4C . . 117.6(4) ?
C5C C6C N1C . . 118.2(4) ?
C5C C6C H6C . . 120.9 ?
N1C C6C H6C . . 120.9 ?
C4C N41C H41E . . 120.0 ?
C4C N41C H41F . . 120.0 ?
H41E N41C H41F . . 120.0 ?
C6D N1D C2D . . 122.3(4) ?
C6D N1D H1D . . 118.9 ?
C2D N1D H1D . . 118.9 ?
O21D C2D N3D . . 121.5(4) ?
O21D C2D N1D . . 119.5(4) ?
N3D C2D N1D . . 119.0(4) ?
C4D N3D C2D . . 119.5(4) ?
N41D C4D N3D . . 119.1(4) ?
N41D C4D C5D . . 121.0(4) ?
N3D C4D C5D . . 119.9(4) ?
C6D C5D F51D . . 122.5(4) ?
C6D C5D C4D . . 120.4(4) ?
F51D C5D C4D . . 117.1(4) ?
C5D C6D N1D . . 118.8(4) ?
C5D C6D H6D . . 120.6 ?
N1D C6D H6D . . 120.6 ?
C4D N41D H41G . . 120.0 ?
C4D N41D H41H . . 120.0 ?
H41G N41D H41H . . 120.0 ?
H1WA O1W H1WB . . 109(4) ?
H2WA O2W H2WB . . 107(3) ?
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
N1A C6A . 1.361(6) ?
N1A C2A . 1.371(5) ?
N1A H1A . 0.8800 ?
C2A O21A . 1.256(5) ?
C2A N3A . 1.366(5) ?
N3A C4A . 1.332(5) ?
C4A N41A . 1.333(6) ?
C4A C5A . 1.413(6) ?
C5A C6A . 1.334(7) ?
C5A F51A . 1.357(5) ?
C6A H6A . 0.9500 ?
N41A H41A . 0.8800 ?
N41A H41B . 0.8800 ?
N1B C6B . 1.353(6) ?
N1B C2B . 1.372(5) ?
N1B H1B . 0.8800 ?
C2B O21B . 1.249(5) ?
C2B N3B . 1.359(5) ?
N3B C4B . 1.328(6) ?
C4B N41B . 1.333(5) ?
C4B C5B . 1.415(6) ?
C5B C6B . 1.346(6) ?
C5B F51B . 1.369(5) ?
C6B H6B . 0.9500 ?
N41B H41C . 0.8800 ?
N41B H41D . 0.8800 ?
N1C C6C . 1.366(6) ?
N1C C2C . 1.373(5) ?
N1C H1C . 0.8800 ?
C2C O21C . 1.252(5) ?
C2C N3C . 1.362(5) ?
N3C C4C . 1.331(5) ?
C4C N41C . 1.318(6) ?
C4C C5C . 1.427(6) ?
C5C C6C . 1.330(7) ?
C5C F51C . 1.362(5) ?
C6C H6C . 0.9500 ?
N41C H41E . 0.8800 ?
N41C H41F . 0.8800 ?
N1D C6D . 1.360(6) ?
N1D C2D . 1.373(6) ?
N1D H1D . 0.8800 ?
C2D O21D . 1.251(5) ?
C2D N3D . 1.366(6) ?
N3D C4D . 1.347(6) ?
C4D N41D . 1.335(5) ?
C4D C5D . 1.421(6) ?
C5D C6D . 1.321(6) ?
C5D F51D . 1.355(5) ?
C6D H6D . 0.9500 ?
N41D H41G . 0.8800 ?
N41D H41H . 0.8800 ?
O1W H1WA . 0.87(2) ?
O1W H1WB . 0.90(2) ?
O2W H2WA . 0.90(2) ?
O2W H2WB . 0.88(2) ?
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
N1A H1A N3B 3 0.88 1.98 2.853(5) 172
N41A H41A O21B . 0.88 1.99 2.858(5) 170
N1B H1B N3A . 0.88 1.97 2.854(5) 177
N41B H41C O21A 3_445 0.88 1.99 2.869(5) 176
N41B H41D O1W 2_464 0.88 2.10 2.972(5) 170
N1C H1C N3D 3_455 0.88 1.99 2.861(5) 173
N41C H41E O21D . 0.88 1.95 2.834(5) 177
N1D H1D N3C . 0.88 1.98 2.862(5) 178
N41D H41G O21C 3_545 0.88 1.98 2.862(5) 175
N41D H41H O2W 2_665 0.88 2.10 2.961(5) 164
O1W H1WA O21B 4 0.87(2) 2.06(3) 2.906(5) 163(4)
O1W H1WB O21C . 0.90(2) 1.93(3) 2.786(5) 158(5)
O2W H2WA O21A . 0.90(2) 1.95(2) 2.826(5) 166(5)
O2W H2WB O21D 4_454 0.88(2) 2.05(3) 2.898(5) 163(4)
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
C6A N1A C2A O21A . . . . -179.5(4) ?
C6A N1A C2A N3A . . . . 0.8(6) ?
O21A C2A N3A C4A . . . . 178.8(4) ?
N1A C2A N3A C4A . . . . -1.6(6) ?
C2A N3A C4A N41A . . . . -178.0(4) ?
C2A N3A C4A C5A . . . . 0.9(6) ?
N3A C4A C5A C6A . . . . 0.5(7) ?
N41A C4A C5A C6A . . . . 179.4(4) ?
N3A C4A C5A F51A . . . . 178.4(4) ?
N41A C4A C5A F51A . . . . -2.7(6) ?
F51A C5A C6A N1A . . . . -179.1(4) ?
C4A C5A C6A N1A . . . . -1.2(7) ?
C2A N1A C6A C5A . . . . 0.6(6) ?
C6B N1B C2B O21B . . . . -178.7(4) ?
C6B N1B C2B N3B . . . . 1.2(6) ?
O21B C2B N3B C4B . . . . -179.7(4) ?
N1B C2B N3B C4B . . . . 0.4(6) ?
C2B N3B C4B N41B . . . . 177.8(4) ?
C2B N3B C4B C5B . . . . -1.9(6) ?
N3B C4B C5B C6B . . . . 1.9(7) ?
N41B C4B C5B C6B . . . . -177.8(4) ?
N3B C4B C5B F51B . . . . -179.2(4) ?
N41B C4B C5B F51B . . . . 1.1(6) ?
F51B C5B C6B N1B . . . . -179.2(4) ?
C4B C5B C6B N1B . . . . -0.3(6) ?
C2B N1B C6B C5B . . . . -1.2(6) ?
C6C N1C C2C O21C . . . . 179.4(4) ?
C6C N1C C2C N3C . . . . -0.9(6) ?
O21C C2C N3C C4C . . . . 179.1(4) ?
N1C C2C N3C C4C . . . . -0.7(6) ?
C2C N3C C4C N41C . . . . -178.2(4) ?
C2C N3C C4C C5C . . . . 1.4(6) ?
N41C C4C C5C C6C . . . . 179.1(4) ?
N3C C4C C5C C6C . . . . -0.5(6) ?
N41C C4C C5C F51C . . . . -1.2(6) ?
N3C C4C C5C F51C . . . . 179.2(4) ?
F51C C5C C6C N1C . . . . 179.3(4) ?
C4C C5C C6C N1C . . . . -1.0(7) ?
C2C N1C C6C C5C . . . . 1.7(6) ?
C6D N1D C2D O21D . . . . -177.8(4) ?
C6D N1D C2D N3D . . . . 2.4(6) ?
O21D C2D N3D C4D . . . . -180.0(4) ?
N1D C2D N3D C4D . . . . -0.2(6) ?
C2D N3D C4D N41D . . . . 177.1(4) ?
C2D N3D C4D C5D . . . . -2.9(6) ?
N41D C4D C5D C6D . . . . -175.9(4) ?
N3D C4D C5D C6D . . . . 4.0(7) ?
N41D C4D C5D F51D . . . . 1.8(6) ?
N3D C4D C5D F51D . . . . -178.2(4) ?
F51D C5D C6D N1D . . . . -179.5(4) ?
C4D C5D C6D N1D . . . . -1.9(7) ?
C2D N1D C6D C5D . . . . -1.3(7) ?
