#------------------------------------------------------------------------------
#$Date: 2012-09-06 14:56:02 +0100 (Thu, 06 Sep 2012) $
#$Revision: 65858 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/51/2105166.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_2105166
loop_
_publ_author_name
'Tutughamiarso, Maya'
'Egert, Ernst'
_publ_section_title
;
 Cocrystals of 5-fluorocytosine. II. Coformers with variable
 hydrogen-bonding sites
;
_journal_coeditor_code           GP5053
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              444
_journal_page_last               452
_journal_volume                  68
_journal_year                    2012
_chemical_formula_moiety         'C4 H4 F N3 O, C2 H5 N3 O2, C2 H6 O S'
_chemical_formula_sum            'C8 H15 F N6 O4 S'
_chemical_formula_weight         310.32
_chemical_name_systematic
;
 ;
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.163(15)
_cell_angle_beta                 96.337(15)
_cell_angle_gamma                105.703(16)
_cell_formula_units_Z            2
_cell_length_a                   8.4065(17)
_cell_length_b                   8.9045(18)
_cell_length_c                   10.6441(19)
_cell_measurement_reflns_used    4300
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.87
_cell_measurement_theta_min      3.39
_cell_volume                     695.8(3)
_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 (Macrae et al., 2008) and XP (Sheldrick, 2008);'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       \w
_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  0.1437
_diffrn_reflns_av_sigmaI/netI    0.1509
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4530
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.74
_diffrn_reflns_theta_min         3.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  0.9483
_exptl_absorpt_correction_T_min  0.8557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULABS (Blessing, 1995; Spek, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.852
_refine_ls_extinction_coef       0.07(2)
_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   0.970
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2617
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.1310
_refine_ls_R_factor_gt           0.0943
_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^)+(0.1896P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2447
_refine_ls_wR_factor_ref         0.2820
_reflns_number_gt                1669
_reflns_number_total             2617
_reflns_threshold_expression     I>2\s(I)
_iucr_refine_instructions_details
;
TITL mt7-53 in P-1
CELL 0.71073   8.4065   8.9045  10.6441 111.163  96.337 105.703
ZERR    2.00   0.0017   0.0018   0.0019   0.015   0.015   0.016
LATT  1
SFAC C H N O F S
UNIT 16 30 12 8 2 2
REM gelbe Nadel
SIZE 0.2 0.3 0.6
ACTA 50
L.S. 10
BOND $H
CONF
FMAP 2
PLAN 10
TEMP -100
DFIX 0.88 0.02 N1 H11 N1 H12
DFIX 0.88 0.02 N3 H3 N1' H1'
DFIX 0.88 0.02 N5 H51 N5 H52
DFIX 0.88 0.02 N41' H41 N41' H42
EQIV $1 x+1, y, z
EQIV $2 x-1, y, z
EQIV $3 -x+1, -y, -z+2
HTAB N1' O21_$1
HTAB N41' O21
HTAB N41' O1A
HTAB N1 O21'_$2
HTAB N1 O41
HTAB N3 N3'
HTAB N5 O41_$3
HTAB N5 O21'
WGHT    0.189600
EXTI    0.066558
FVAR       0.56843
N1'   3    0.871570    0.255742    0.540471    11.00000    0.02334    0.04820 =
         0.02680    0.01964    0.00751    0.01167
H1'   2    0.967159    0.238747    0.557195    11.00000   -1.20000
C2'   1    0.755591    0.220978    0.616781    11.00000    0.02138    0.04449 =
         0.02875    0.01967    0.00480    0.00788
O21'  4    0.798157    0.187252    0.716771    11.00000    0.02942    0.06016 =
         0.03675    0.03330    0.01083    0.02078
N3'   3    0.597905    0.231429    0.585202    11.00000    0.01944    0.03450 =
         0.02988    0.01504    0.00164    0.00719
C4'   1    0.557198    0.273801    0.480487    11.00000    0.02416    0.03144 =
         0.02768    0.01392    0.00594    0.00945
N41'  3    0.402934    0.282295    0.451962    11.00000    0.02512    0.05506 =
         0.03570    0.03056    0.00712    0.01663
H41   2    0.360384    0.298023    0.380799    11.00000   -1.20000
H42   2    0.346726    0.288088    0.518507    11.00000   -1.20000
C5'   1    0.681409    0.315446    0.404977    11.00000    0.03167    0.04128 =
         0.02542    0.02012    0.00615    0.01222
F51'  5    0.635890    0.362507    0.301987    11.00000    0.04015    0.05547 =
         0.03857    0.03339    0.01115    0.01911
C6'   1    0.835484    0.303983    0.435237    11.00000    0.02850    0.03575 =
         0.02503    0.01560    0.00720    0.00280
AFIX  43
H6'   2    0.917904    0.328793    0.384765    11.00000   -1.20000
AFIX   0
N1    3    0.068261    0.064143    0.751745    11.00000    0.02459    0.05325 =
         0.03912    0.03017    0.00799    0.01413
H11   2    0.080596    0.014918    0.808647    11.00000   -1.20000
H12   2   -0.029425    0.079459    0.728612    11.00000   -1.20000
C2    1    0.195929    0.130556    0.701985    11.00000    0.02127    0.03448 =
         0.02513    0.01324    0.00291    0.00863
O21   4    0.178447    0.195473    0.618685    11.00000    0.02454    0.05965 =
         0.04127    0.03466    0.01009    0.01359
N3    3    0.354478    0.119753    0.742411    11.00000    0.01775    0.04378 =
         0.02832    0.02317    0.00264    0.00607
H3    2    0.420923    0.151194    0.691010    11.00000   -1.20000
C4    1    0.402765    0.061117    0.840335    11.00000    0.02978    0.03268 =
         0.02279    0.01326    0.00136    0.00890
O41   4    0.303547    0.008804    0.906284    11.00000    0.02911    0.05335 =
         0.03489    0.03039    0.01034    0.01683
N5    3    0.563946    0.064698    0.858611    11.00000    0.02027    0.06201 =
         0.03715    0.03145    0.00251    0.00920
H51   2    0.587274    0.027666    0.921933    11.00000   -1.20000
H52   2    0.616877    0.075942    0.794926    11.00000   -1.20000
S1A   6    0.120390    0.278304    0.122865    11.00000    0.04795    0.04195 =
         0.03839    0.01998    0.01088    0.01085
O1A   4    0.164692    0.339486    0.278510    11.00000    0.04266    0.08632 =
         0.04065    0.03983    0.01132    0.03038
C1A   1   -0.044288    0.358718    0.088054    11.00000    0.03749    0.05842 =
         0.03742    0.02741   -0.01069    0.00027
AFIX 137
H1A1  2   -0.147714    0.299067    0.108473    11.00000   -1.50000
H1A2  2   -0.066928    0.339865   -0.009724    11.00000   -1.50000
H1A3  2   -0.008702    0.481405    0.146287    11.00000   -1.50000
AFIX   0
C2A   1    0.288428    0.416042    0.083822    11.00000    0.04841    0.05450 =
         0.03604    0.01510    0.01498    0.00640
AFIX 137
H2A1  2    0.309386    0.535317    0.145613    11.00000   -1.50000
H2A2  2    0.255417    0.400174   -0.012545    11.00000   -1.50000
H2A3  2    0.392079    0.387714    0.097115    11.00000   -1.50000
HKLF 4
REM  mt7-53 in P-1
REM R1 =  0.0943 for   1669 Fo > 4sig(Fo)  and  0.1310 for all   2617 data
REM    208 parameters refined using      8 restraints
END
;
_[local]_cod_data_source_file    gp5053.cif
_[local]_cod_data_source_block   I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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        695.8(2)
_cod_database_code               2105166
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
N N1' 0.8716(5) 0.2557(6) 0.5405(4) 0.0314(10) Uani d D 1 1
H H1' 0.967(4) 0.239(7) 0.557(6) 0.038 Uiso d D 1 1
C C2' 0.7556(6) 0.2210(7) 0.6168(5) 0.0309(11) Uani d . 1 1
O O21' 0.7982(4) 0.1873(5) 0.7168(3) 0.0365(9) Uani d . 1 1
N N3' 0.5979(5) 0.2314(5) 0.5852(4) 0.0281(9) Uani d . 1 1
C C4' 0.5572(6) 0.2738(6) 0.4805(5) 0.0272(10) Uani d . 1 1
N N41' 0.4029(5) 0.2823(6) 0.4520(4) 0.0343(10) Uani d D 1 1
H H41 0.360(7) 0.298(7) 0.381(4) 0.041 Uiso d D 1 1
H H42 0.347(7) 0.288(8) 0.519(4) 0.041 Uiso d D 1 1
C C5' 0.6814(6) 0.3154(7) 0.4050(5) 0.0309(11) Uani d . 1 1
F F51' 0.6359(4) 0.3625(4) 0.3020(3) 0.0396(8) Uani d . 1 1
C C6' 0.8355(6) 0.3040(6) 0.4352(5) 0.0305(11) Uani d . 1 1
H H6' 0.9179 0.3288 0.3848 0.037 Uiso calc R 1 1
N N1 0.0683(5) 0.0641(6) 0.7517(4) 0.0353(10) Uani d D 1 1
H H11 0.081(8) 0.015(7) 0.809(5) 0.042 Uiso d D 1 1
H H12 -0.029(5) 0.079(7) 0.729(6) 0.042 Uiso d D 1 1
C C2 0.1959(6) 0.1306(6) 0.7020(4) 0.0270(10) Uani d . 1 1
O O21 0.1784(4) 0.1955(5) 0.6187(3) 0.0375(9) Uani d . 1 1
N N3 0.3545(5) 0.1198(5) 0.7424(4) 0.0286(9) Uani d D 1 1
H H3 0.421(6) 0.151(7) 0.691(5) 0.034 Uiso d D 1 1
C C4 0.4028(6) 0.0611(6) 0.8403(4) 0.0286(10) Uani d . 1 1
O O41 0.3035(4) 0.0088(5) 0.9063(3) 0.0345(9) Uani d . 1 1
N N5 0.5639(5) 0.0647(6) 0.8586(4) 0.0378(11) Uani d D 1 1
H H51 0.587(8) 0.028(7) 0.922(5) 0.045 Uiso d D 1 1
H H52 0.617(7) 0.076(8) 0.795(5) 0.045 Uiso d D 1 1
S S1A 0.12039(19) 0.27830(19) 0.12286(14) 0.0425(5) Uani d . 1 1
O O1A 0.1647(5) 0.3395(6) 0.2785(4) 0.0503(11) Uani d . 1 1
C C1A -0.0443(7) 0.3587(8) 0.0881(6) 0.0472(15) Uani d . 1 1
H H1A1 -0.1477 0.2991 0.1085 0.071 Uiso calc R 1 1
H H1A2 -0.0669 0.3399 -0.0097 0.071 Uiso calc R 1 1
H H1A3 -0.0087 0.4814 0.1463 0.071 Uiso calc R 1 1
C C2A 0.2884(8) 0.4160(8) 0.0838(6) 0.0493(15) Uani d . 1 1
H H2A1 0.3094 0.5353 0.1456 0.074 Uiso calc R 1 1
H H2A2 0.2554 0.4002 -0.0125 0.074 Uiso calc R 1 1
H H2A3 0.3921 0.3877 0.0971 0.074 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1' 0.023(2) 0.048(3) 0.0268(19) 0.0117(18) 0.0075(15) 0.0196(19)
C2' 0.021(2) 0.044(3) 0.029(2) 0.008(2) 0.0048(17) 0.020(2)
O21' 0.0294(19) 0.060(2) 0.0368(18) 0.0208(17) 0.0108(14) 0.0333(18)
N3' 0.0194(19) 0.034(2) 0.0299(19) 0.0072(16) 0.0016(15) 0.0150(17)
C4' 0.024(2) 0.031(3) 0.028(2) 0.0095(19) 0.0059(17) 0.0139(19)
N41' 0.025(2) 0.055(3) 0.036(2) 0.017(2) 0.0071(17) 0.031(2)
C5' 0.032(3) 0.041(3) 0.025(2) 0.012(2) 0.0062(18) 0.020(2)
F51' 0.0402(17) 0.055(2) 0.0386(15) 0.0191(14) 0.0112(12) 0.0334(15)
C6' 0.028(2) 0.036(3) 0.025(2) 0.003(2) 0.0072(17) 0.016(2)
N1 0.025(2) 0.053(3) 0.039(2) 0.014(2) 0.0080(17) 0.030(2)
C2 0.021(2) 0.034(3) 0.025(2) 0.0086(19) 0.0029(16) 0.0132(19)
O21 0.0245(18) 0.060(2) 0.0413(19) 0.0136(16) 0.0101(14) 0.0347(18)
N3 0.0177(19) 0.044(3) 0.0283(19) 0.0061(17) 0.0026(14) 0.0232(19)
C4 0.030(3) 0.033(3) 0.023(2) 0.009(2) 0.0014(17) 0.0133(19)
O41 0.0291(18) 0.053(2) 0.0349(17) 0.0168(16) 0.0103(14) 0.0304(17)
N5 0.020(2) 0.062(3) 0.037(2) 0.0092(19) 0.0025(16) 0.031(2)
S1A 0.0480(9) 0.0420(9) 0.0384(8) 0.0108(6) 0.0109(6) 0.0200(6)
O1A 0.043(2) 0.086(3) 0.041(2) 0.030(2) 0.0113(17) 0.040(2)
C1A 0.037(3) 0.058(4) 0.037(3) 0.000(3) -0.011(2) 0.027(3)
C2A 0.048(3) 0.055(4) 0.036(3) 0.006(3) 0.015(2) 0.015(3)
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'
S S 0.1246 0.1234 '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
C6' N1' C2' 122.1(4)
C6' N1' H1' 120(4)
C2' N1' H1' 118(4)
O21' C2' N3' 121.1(4)
O21' C2' N1' 119.6(4)
N3' C2' N1' 119.3(4)
C4' N3' C2' 120.0(4)
N41' C4' N3' 118.6(4)
N41' C4' C5' 121.3(4)
N3' C4' C5' 120.0(4)
C4' N41' H41 126(4)
C4' N41' H42 115(4)
H41 N41' H42 119(5)
C6' C5' F51' 122.1(4)
C6' C5' C4' 119.9(4)
F51' C5' C4' 118.0(4)
C5' C6' N1' 118.6(4)
C5' C6' H6' 120.7
N1' C6' H6' 120.7
C2 N1 H11 123(4)
C2 N1 H12 116(4)
H11 N1 H12 121(6)
O21 C2 N1 123.2(4)
O21 C2 N3 118.7(4)
N1 C2 N3 118.0(4)
C4 N3 C2 127.6(4)
C4 N3 H3 124(4)
C2 N3 H3 108(4)
O41 C4 N5 122.3(4)
O41 C4 N3 122.8(4)
N5 C4 N3 114.9(4)
C4 N5 H51 111(4)
C4 N5 H52 117(4)
H51 N5 H52 130(6)
O1A S1A C1A 104.9(3)
O1A S1A C2A 105.4(3)
C1A S1A C2A 98.5(3)
S1A C1A H1A1 109.5
S1A C1A H1A2 109.5
H1A1 C1A H1A2 109.5
S1A C1A H1A3 109.5
H1A1 C1A H1A3 109.5
H1A2 C1A H1A3 109.5
S1A C2A H2A1 109.5
S1A C2A H2A2 109.5
H2A1 C2A H2A2 109.5
S1A C2A H2A3 109.5
H2A1 C2A H2A3 109.5
H2A2 C2A H2A3 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1' C6' 1.369(6)
N1' C2' 1.378(6)
N1' H1' 0.87(2)
C2' O21' 1.247(5)
C2' N3' 1.367(6)
N3' C4' 1.338(6)
C4' N41' 1.328(6)
C4' C5' 1.437(7)
N41' H41 0.87(2)
N41' H42 0.89(2)
C5' C6' 1.340(7)
C5' F51' 1.360(5)
C6' H6' 0.9500
N1 C2 1.338(6)
N1 H11 0.88(2)
N1 H12 0.89(2)
C2 O21 1.237(5)
C2 N3 1.394(6)
N3 C4 1.392(6)
N3 H3 0.88(2)
C4 O41 1.249(6)
C4 N5 1.337(6)
N5 H51 0.88(2)
N5 H52 0.87(2)
S1A O1A 1.511(4)
S1A C1A 1.784(6)
S1A C2A 1.798(6)
C1A H1A1 0.9800
C1A H1A2 0.9800
C1A H1A3 0.9800
C2A H2A1 0.9800
C2A H2A2 0.9800
C2A H2A3 0.9800
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
N1' H1' O21 1_655 0.87(2) 2.01(2) 2.870(5) 172(5)
N41' H42 O21 . 0.89(2) 2.04(3) 2.872(5) 156(6)
N41' H41 O1A . 0.87(2) 2.06(4) 2.845(5) 149(5)
N1 H12 O21' 1_455 0.89(2) 1.96(3) 2.820(5) 162(5)
N1 H11 O41 . 0.88(2) 2.06(5) 2.694(5) 128(5)
N3 H3 N3' . 0.88(2) 2.09(2) 2.972(5) 174(5)
N5 H51 O41 2_657 0.88(2) 2.12(3) 2.982(5) 166(6)
N5 H52 O21' . 0.87(2) 2.01(3) 2.834(6) 156(6)
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
C6' N1' C2' O21' -175.8(5)
C6' N1' C2' N3' 1.3(7)
O21' C2' N3' C4' 177.6(5)
N1' C2' N3' C4' 0.5(7)
C2' N3' C4' N41' 179.8(5)
C2' N3' C4' C5' -2.7(7)
N41' C4' C5' C6' -179.3(5)
N3' C4' C5' C6' 3.2(8)
N41' C4' C5' F51' -0.6(7)
N3' C4' C5' F51' -178.1(4)
F51' C5' C6' N1' 180.0(4)
C4' C5' C6' N1' -1.4(8)
C2' N1' C6' C5' -0.8(8)
O21 C2 N3 C4 175.9(4)
N1 C2 N3 C4 -6.5(8)
C2 N3 C4 O41 0.0(8)
C2 N3 C4 N5 179.9(5)