#------------------------------------------------------------------------------
#$Date: 2018-09-23 20:13:03 +0300 (Sun, 23 Sep 2018) $
#$Revision: 211129 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/46/4504657.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4504657
loop_
_publ_author_name
'Hulme, Ashley T.'
'Tocher, Derek A.'
_publ_section_title
;
 The Discovery of New Crystal Forms of 5-Fluorocytosine Consistent with
 the Results of Computational Crystal Structure Prediction
;
_journal_coden_ASTM              CGDEFU
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              481
_journal_page_last               487
_journal_paper_doi               10.1021/cg050398g
_journal_volume                  6
_journal_year                    2006
_chemical_formula_moiety         'C4 H4 F N3 O, H2 0'
_chemical_formula_sum            'C4 H6 F N3 O2'
_chemical_formula_weight         147.12
_chemical_name_systematic
;
 5-fluorocytosine monohydrate II
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.036(2)
_cell_angle_beta                 100.460(2)
_cell_angle_gamma                96.710(2)
_cell_formula_units_Z            2
_cell_length_a                   4.1026(5)
_cell_length_b                   8.2731(10)
_cell_length_c                   9.9191(12)
_cell_measurement_reflns_used    1629
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.9925
_cell_measurement_theta_min      2.249
_cell_volume                     305.14(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0117
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2672
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_correction_T_min  0.9413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             152
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1381
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0368
_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)+(0.0706P)²+0.0554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1096
_reflns_number_gt                1278
_reflns_number_total             1381
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg050398gsi20050809_092746.cif
_cod_data_source_block           str0312
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4504657
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F5 F 0.96187(17) 1.07169(8) 0.15065(7) 0.0276(2) Uani 1 1 d .
O2 O 0.0751(2) 0.57917(10) 0.19429(8) 0.0255(2) Uani 1 1 d .
N4 N 0.7980(2) 1.11235(12) 0.41271(10) 0.0234(2) Uani 1 1 d .
H2 H 0.729(4) 1.122(2) 0.4928(19) 0.029(3) Uiso 1 1 d .
H3 H 0.927(4) 1.188(2) 0.4027(19) 0.036(4) Uiso 1 1 d .
N3 N 0.4353(2) 0.84333(11) 0.30838(9) 0.0195(2) Uani 1 1 d .
N1 N 0.3456(2) 0.68191(11) 0.05245(9) 0.0192(2) Uani 1 1 d .
H1 H 0.217(4) 0.591(2) -0.025(2) 0.037(4) Uiso 1 1 d .
C6 C 0.5730(3) 0.80392(14) 0.03689(11) 0.0199(2) Uani 1 1 d .
H6 H 0.603(4) 0.782(2) -0.0599(18) 0.030(4) Uiso 1 1 d .
C5 C 0.7321(3) 0.94504(13) 0.15685(11) 0.0196(2) Uani 1 1 d .
C4 C 0.6544(3) 0.96786(13) 0.29663(11) 0.0183(2) Uani 1 1 d .
C2 C 0.2817(3) 0.69865(13) 0.18762(11) 0.0187(2) Uani 1 1 d .
O3 O 0.1913(3) 0.43298(14) 0.40690(12) 0.0555(4) Uani 1 1 d D
H7 H 0.171(5) 0.476(3) 0.338(2) 0.072(6) Uiso 1 1 d D
H8B H 0.0000 0.5000 0.5000 0.108(13) Uiso 1 2 d S
H8A H 0.402(3) 0.469(4) 0.448(3) 0.025(7) Uiso 0.50 1 d PD
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F5 0.0300(4) 0.0263(4) 0.0229(4) 0.0079(3) 0.0087(3) -0.0081(3)
O2 0.0316(4) 0.0225(4) 0.0170(4) 0.0063(3) 0.0030(3) -0.0076(3)
N4 0.0300(5) 0.0181(4) 0.0178(5) 0.0045(3) 0.0055(4) -0.0044(4)
N3 0.0233(5) 0.0180(4) 0.0148(4) 0.0047(3) 0.0043(3) -0.0004(3)
N1 0.0226(4) 0.0174(4) 0.0144(4) 0.0036(3) 0.0036(3) -0.0001(3)
C6 0.0216(5) 0.0219(5) 0.0168(5) 0.0073(4) 0.0067(4) 0.0032(4)
C5 0.0195(5) 0.0197(5) 0.0203(5) 0.0089(4) 0.0057(4) 0.0005(4)
C4 0.0196(5) 0.0174(5) 0.0170(5) 0.0063(4) 0.0033(4) 0.0023(4)
C2 0.0212(5) 0.0179(5) 0.0161(5) 0.0063(4) 0.0035(4) 0.0016(4)
O3 0.0793(9) 0.0387(6) 0.0355(6) 0.0216(5) -0.0119(5) -0.0215(5)
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'
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'
F F 0.0171 0.0103 '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
C4 N4 H2 115.5(10)
C4 N4 H3 118.9(12)
H2 N4 H3 125.3(16)
C4 N3 C2 119.88(9)
C6 N1 C2 121.79(9)
C6 N1 H1 121.9(11)
C2 N1 H1 116.1(11)
C5 C6 N1 118.40(9)
C5 C6 H6 125.3(9)
N1 C6 H6 116.3(9)
C6 C5 F5 121.99(9)
C6 C5 C4 120.14(10)
F5 C5 C4 117.85(9)
N4 C4 N3 120.47(9)
N4 C4 C5 119.80(10)
N3 C4 C5 119.72(9)
O2 C2 N3 121.72(9)
O2 C2 N1 118.32(9)
N3 C2 N1 119.95(9)
H7 O3 H8B 110.0
H7 O3 H8A 101(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F5 C5 1.3507(11)
O2 C2 1.2526(13)
N4 C4 1.3220(13)
N4 H2 0.872(17)
N4 H3 0.814(18)
N3 C4 1.3368(13)
N3 C2 1.3535(13)
N1 C6 1.3608(13)
N1 C2 1.3765(13)
N1 H1 0.896(19)
C6 C5 1.3391(15)
C6 H6 0.948(16)
C5 C4 1.4335(15)
O3 H7 0.87(2)
O3 H8B 1.3379
O3 H8A 0.856(10)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H2 N3 0.872(17) 2.137(17) 3.0087(14) 178.0(14) 2_676
N4 H3 O3 0.814(18) 2.170(18) 2.9633(14) 164.9(16) 1_665
N1 H1 O2 0.896(19) 1.867(19) 2.7581(12) 173.1(15) 2_565
O3 H7 O2 0.87(2) 1.90(2) 2.7668(13) 173(2) .
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
C2 N1 C6 C5 -1.28(15)
N1 C6 C5 F5 179.80(8)
N1 C6 C5 C4 -1.92(15)
C2 N3 C4 N4 177.84(9)
C2 N3 C4 C5 -1.70(15)
C6 C5 C4 N4 -176.07(10)
F5 C5 C4 N4 2.28(15)
C6 C5 C4 N3 3.47(15)
F5 C5 C4 N3 -178.18(8)
C4 N3 C2 O2 179.97(9)
C4 N3 C2 N1 -1.45(15)
C6 N1 C2 O2 -178.31(9)
C6 N1 C2 N3 3.06(15)
