#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:20:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180501 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/70/7217044.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_7217044
loop_
_publ_author_name
'Li, Song'
'Chen, Jia-Mei'
'Lu, Tong-Bu'
_publ_section_title
;
 Synthon polymorphs of 1 : 1 co-crystal of 5-fluorouracil
 and 4-hydroxybenzoic acid: their relative stability and solvent polarity
 dependence of grinding outcomes
;
_journal_issue                   28
_journal_name_full               CrystEngComm
_journal_page_first              6450
_journal_paper_doi               10.1039/c4ce00221k
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C11 H9 F N2 O5'
_chemical_formula_weight         268.20
_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                67.906(10)
_cell_angle_beta                 86.057(8)
_cell_angle_gamma                78.308(8)
_cell_formula_units_Z            2
_cell_length_a                   6.8225(6)
_cell_length_b                   8.6115(9)
_cell_length_c                   10.7203(12)
_cell_measurement_reflns_used    1192
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      64.7560
_cell_measurement_theta_min      4.4330
_cell_volume                     571.46(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 10.5058
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3293
_diffrn_reflns_theta_full        62.94
_diffrn_reflns_theta_max         62.94
_diffrn_reflns_theta_min         4.45
_exptl_absorpt_coefficient_mu    1.176
_exptl_absorpt_correction_T_max  0.8915
_exptl_absorpt_correction_T_min  0.7989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0687P)²+0.0355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1266
_reflns_number_gt                1387
_reflns_number_total             1808
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00221k2.cif
_cod_data_source_block           exp_6273
_cod_original_cell_volume        571.46(10)
_cod_database_code               7217044
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
N1 N 0.1213(3) 0.2884(2) 0.62119(18) 0.0225(4) Uani 1 1 d .
F1 F 0.3539(2) -0.12438(15) 0.84625(14) 0.0383(4) Uani 1 1 d .
O2 O 0.2544(2) 0.51082(18) 0.47665(15) 0.0273(4) Uani 1 1 d .
O1 O -0.0215(2) 0.07212(19) 0.76358(16) 0.0313(4) Uani 1 1 d .
N2 N 0.4630(3) 0.2682(2) 0.60408(19) 0.0256(5) Uani 1 1 d .
C4 C 0.3332(3) 0.0356(3) 0.7537(2) 0.0264(5) Uani 1 1 d .
C2 C 0.2784(3) 0.3638(3) 0.5626(2) 0.0224(5) Uani 1 1 d .
C3 C 0.4906(3) 0.1053(3) 0.6993(2) 0.0272(5) Uani 1 1 d .
H3A H 0.6194 0.0439 0.7256 0.033 Uiso 1 1 calc R
C1 C 0.1315(3) 0.1261(3) 0.7180(2) 0.0240(5) Uani 1 1 d .
H2 H 0.567(4) 0.326(3) 0.569(3) 0.053(8) Uiso 1 1 d .
H1 H -0.002(4) 0.355(3) 0.593(3) 0.042(7) Uiso 1 1 d .
O3 O -0.2224(2) -0.1269(2) 0.95668(17) 0.0398(5) Uani 1 1 d .
H3 H -0.1214 -0.0924 0.9206 0.060 Uiso 1 1 calc R
C8 C -0.0860(3) -0.6102(3) 1.2503(2) 0.0259(5) Uani 1 1 d .
O5 O -0.1848(2) -0.84788(19) 1.42293(16) 0.0342(4) Uani 1 1 d .
O4 O 0.1419(2) -0.84906(19) 1.38619(16) 0.0323(4) Uani 1 1 d .
H4 H 0.1502 -0.9445 1.4450 0.049 Uiso 1 1 calc R
C5 C -0.1700(3) -0.2862(3) 1.0504(2) 0.0290(6) Uani 1 1 d .
C11 C -0.0476(3) -0.7781(3) 1.3589(2) 0.0268(5) Uani 1 1 d .
C10 C -0.3257(4) -0.3677(3) 1.1136(2) 0.0311(6) Uani 1 1 d .
H10 H -0.4577 -0.3142 1.0893 0.037 Uiso 1 1 calc R
C7 C 0.0689(3) -0.5268(3) 1.1847(2) 0.0281(5) Uani 1 1 d .
H7 H 0.2012 -0.5803 1.2081 0.034 Uiso 1 1 calc R
C9 C -0.2836(3) -0.5284(3) 1.2128(2) 0.0294(6) Uani 1 1 d .
H9 H -0.3880 -0.5830 1.2552 0.035 Uiso 1 1 calc R
C6 C 0.0277(3) -0.3658(3) 1.0853(2) 0.0295(6) Uani 1 1 d .
H6 H 0.1315 -0.3111 1.0421 0.035 Uiso 1 1 calc R
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
C2 N1 C1 126.64(19)
C2 N1 H1 114.8(15)
C1 N1 H1 118.5(15)
C2 N2 C3 122.42(19)
C2 N2 H2 114.1(17)
C3 N2 H2 123.2(17)
C3 C4 F1 121.8(2)
C3 C4 C1 122.2(2)
F1 C4 C1 116.01(18)
O2 C2 N2 122.15(19)
O2 C2 N1 122.03(19)
N2 C2 N1 115.83(19)
C4 C3 N2 120.0(2)
C4 C3 H3A 120.0
N2 C3 H3A 120.0
O1 C1 N1 120.59(19)
O1 C1 C4 126.4(2)
N1 C1 C4 112.97(18)
C5 O3 H3 109.5
C9 C8 C7 118.8(2)
C9 C8 C11 119.2(2)
C7 C8 C11 122.0(2)
C11 O4 H4 109.5
O3 C5 C10 116.5(2)
O3 C5 C6 123.0(2)
C10 C5 C6 120.5(2)
O5 C11 O4 122.1(2)
O5 C11 C8 122.2(2)
O4 C11 C8 115.71(19)
C9 C10 C5 119.6(2)
C9 C10 H10 120.2
C5 C10 H10 120.2
C6 C7 C8 120.7(2)
C6 C7 H7 119.7
C8 C7 H7 119.7
C10 C9 C8 120.8(2)
C10 C9 H9 119.6
C8 C9 H9 119.6
C7 C6 C5 119.6(2)
C7 C6 H6 120.2
C5 C6 H6 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.359(3)
N1 C1 1.384(3)
N1 H1 0.92(3)
F1 C4 1.347(2)
O2 C2 1.240(2)
O1 C1 1.224(2)
N2 C2 1.358(3)
N2 C3 1.374(3)
N2 H2 0.93(3)
C4 C3 1.328(3)
C4 C1 1.436(3)
C3 H3A 0.9300
O3 C5 1.354(3)
O3 H3 0.8200
C8 C9 1.397(3)
C8 C7 1.398(3)
C8 C11 1.462(3)
O5 C11 1.240(3)
O4 C11 1.314(3)
O4 H4 0.8200
C5 C10 1.387(3)
C5 C6 1.390(3)
C10 C9 1.380(3)
C10 H10 0.9300
C7 C6 1.381(3)
C7 H7 0.9300
C9 H9 0.9300
C6 H6 0.9300
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
N2 H2 O2 0.93(3) 1.94(3) 2.847(2) 164(2) 2_666
N1 H1 O2 0.92(3) 1.89(3) 2.805(2) 176(2) 2_566
O3 H3 O1 0.82 1.94 2.645(2) 144.3 .
O4 H4 O5 0.82 1.80 2.615(2) 176.1 2_538
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
C3 N2 C2 O2 180.0(2)
C3 N2 C2 N1 0.0(3)
C1 N1 C2 O2 -179.7(2)
C1 N1 C2 N2 0.3(3)
F1 C4 C3 N2 179.28(19)
C1 C4 C3 N2 -1.0(4)
C2 N2 C3 C4 0.4(3)
C2 N1 C1 O1 179.9(2)
C2 N1 C1 C4 -0.8(3)
C3 C4 C1 O1 -179.6(2)
F1 C4 C1 O1 0.2(3)
C3 C4 C1 N1 1.2(3)
F1 C4 C1 N1 -179.09(18)
C9 C8 C11 O5 -3.0(3)
C7 C8 C11 O5 175.5(2)
C9 C8 C11 O4 178.3(2)
C7 C8 C11 O4 -3.3(3)
O3 C5 C10 C9 -178.2(2)
C6 C5 C10 C9 0.6(4)
C9 C8 C7 C6 0.6(3)
C11 C8 C7 C6 -177.9(2)
C5 C10 C9 C8 0.0(4)
C7 C8 C9 C10 -0.6(3)
C11 C8 C9 C10 178.0(2)
C8 C7 C6 C5 -0.1(3)
O3 C5 C6 C7 178.2(2)
C10 C5 C6 C7 -0.5(3)
