#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:28:49 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179665 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/18/4511826.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_4511826
loop_
_publ_author_name
'da Silva, Cecília C. P.'
'Pepino, Rebeka de O.'
'de Melo, Cristiane C.'
'Tenorio, Juan C.'
'Ellena, Javier'
_publ_section_title
;
 Controlled Synthesis of New 5-Fluorocytosine Cocrystals Based on the
 pKaRule
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4383
_journal_paper_doi               10.1021/cg500502j
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C4 H4 F N3 O, 0.5(C8 H6 O4)'
_chemical_formula_sum            'C8 H7 F N3 O3'
_chemical_formula_weight         212.17
_chemical_name_common            'Cocrystal 5FC tereftalic acid'
_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
_cell_angle_alpha                107.812(5)
_cell_angle_beta                 92.036(4)
_cell_angle_gamma                96.844(4)
_cell_formula_units_Z            2
_cell_length_a                   3.6265(3)
_cell_length_b                   9.5274(8)
_cell_length_c                   13.7902(12)
_cell_measurement_temperature    100.0(2)
_cell_volume                     449.09(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.974
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7867
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         30.24
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
   R. H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38.  
;
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             218
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0501P)²+0.2329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                2035
_reflns_number_total             2602
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg500502j_si_001.cif
_cod_data_source_block           TEREPHTALIC
_cod_depositor_comments
'Adding full bibliography for 4511824--4511829.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4511826
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
C2 0.8252(4) 0.19087(16) 0.48066(11) 0.0131(3) Uani d . 1 C
C4 0.7015(4) 0.33371(16) 0.37637(11) 0.0119(3) Uani d . 1 C
C5 0.8023(4) 0.22096(16) 0.29073(11) 0.0139(3) Uani d . 1 C
C6 0.9047(4) 0.09593(16) 0.30203(11) 0.0133(3) Uani d . 1 C
H6 0.9663 0.0209 0.2463 0.016 Uiso calc R 1 H
F51 0.7850(3) 0.24281(10) 0.19829(7) 0.0216(2) Uani d . 1 F
N1 0.9159(4) 0.08190(13) 0.39743(9) 0.0131(3) Uani d . 1 N
H1 0.9891 0.0058 0.4103 0.02 Uiso d R 1 H
N3 0.7135(3) 0.31571(13) 0.46899(9) 0.0129(3) Uani d . 1 N
N41 0.5929(4) 0.45554(14) 0.36430(10) 0.0152(3) Uani d . 1 N
H41A 0.53 0.5231 0.4159 0.018 Uiso calc R 1 H
H41B 0.5852 0.4671 0.3048 0.018 Uiso calc R 1 H
O21 0.8498(3) 0.17051(12) 0.56653(8) 0.0183(3) Uani d . 1 O
C7 0.3271(4) 0.69921(16) 0.19171(11) 0.0131(3) Uani d . 1 C
C8 0.4159(4) 0.59425(16) 0.09295(11) 0.0122(3) Uani d . 1 C
C9 0.5511(4) 0.65308(16) 0.01827(11) 0.0139(3) Uani d . 1 C
H9 0.5848 0.7555 0.0307 0.017 Uiso calc R 1 H
C10 0.3644(4) 0.44060(16) 0.07446(11) 0.0136(3) Uani d . 1 C
H10 0.2736 0.4011 0.1242 0.016 Uiso calc R 1 H
O3 0.2416(3) 0.63398(12) 0.26179(8) 0.0189(3) Uani d . 1 O
H3 0.2214 0.7079 0.324 0.028 Uiso d R 1 H
O4 0.3347(3) 0.83162(12) 0.20598(8) 0.0194(3) Uani d . 1 O
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 0 '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 0.006 '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
_geom_angle_site_symmetry_1
O21 C2 N3 121.97(13) .
O21 C2 N1 118.03(13) .
N3 C2 N1 120.00(13) .
N41 C4 N3 120.02(13) .
N41 C4 C5 120.05(13) .
N3 C4 C5 119.93(13) .
C6 C5 F51 121.41(13) .
C6 C5 C4 120.35(13) .
F51 C5 C4 118.23(13) .
C5 C6 N1 118.08(13) .
C5 C6 H6 121 .
N1 C6 H6 121 .
C6 N1 C2 121.99(13) .
C6 N1 H1 122.6 .
C2 N1 H1 115.3 .
C4 N3 C2 119.62(12) .
C4 N41 H41A 120 .
C4 N41 H41B 120 .
H41A N41 H41B 120 .
O4 C7 O3 123.51(13) .
O4 C7 C8 122.78(13) .
O3 C7 C8 113.71(12) .
C9 C8 C10 120.01(13) .
C9 C8 C7 118.43(13) .
C10 C8 C7 121.55(13) .
C10 C9 C8 120.19(13) 2_665
C10 C9 H9 119.9 2_665
C8 C9 H9 119.9 .
C9 C10 C8 119.80(13) 2_665
C9 C10 H10 120.1 2_665
C8 C10 H10 120.1 .
C7 O3 H3 108.8 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C2 O21 . 1.2590(18)
C2 N3 . 1.3533(19)
C2 N1 . 1.3721(18)
C4 N41 . 1.3239(19)
C4 N3 . 1.3396(19)
C4 C5 . 1.4250(19)
C5 C6 . 1.340(2)
C5 F51 . 1.3535(17)
C6 N1 . 1.3622(18)
C6 H6 . 0.93
N1 H1 . 0.8654
N41 H41A . 0.86
N41 H41B . 0.86
C7 O4 . 1.2126(18)
C7 O3 . 1.3263(18)
C7 C8 . 1.4944(19)
C8 C9 . 1.392(2)
C8 C10 . 1.395(2)
C9 C10 2_665 1.3858(19)
C9 H9 . 0.93
C10 C9 2_665 1.3858(19)
C10 H10 . 0.93
O3 H3 . 0.94
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
_geom_torsion_site_symmetry_4
N41 C4 C5 C6 -178.54(14) .
N3 C4 C5 C6 0.9(2) .
N41 C4 C5 F51 0.3(2) .
N3 C4 C5 F51 179.70(13) .
F51 C5 C6 N1 179.95(13) .
C4 C5 C6 N1 -1.3(2) .
C5 C6 N1 C2 0.2(2) .
O21 C2 N1 C6 -178.62(13) .
N3 C2 N1 C6 1.3(2) .
N41 C4 N3 C2 -179.95(14) .
C5 C4 N3 C2 0.6(2) .
O21 C2 N3 C4 178.24(14) .
N1 C2 N3 C4 -1.7(2) .
O4 C7 C8 C9 7.0(2) .
O3 C7 C8 C9 -172.67(13) .
O4 C7 C8 C10 -172.61(15) .
O3 C7 C8 C10 7.7(2) .
C10 C8 C9 C10 -0.1(2) 2_665
C7 C8 C9 C10 -179.78(14) 2_665
C9 C8 C10 C9 0.1(2) 2_665
C7 C8 C10 C9 179.77(14) 2_665
