#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:36:54 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179669 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/22/4512287.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_4512287
loop_
_publ_author_name
'Aitipamula, Srinivasulu'
'Chow, Pui Shan'
'Tan, Reginald B. H.'
_publ_section_title
;
 Crystal Engineering of Tegafur Cocrystals: Structural Analysis and
 Physicochemical Properties
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              6557
_journal_paper_doi               10.1021/cg501469r
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C14 H15 F N4 O4'
_chemical_formula_weight         322.30
_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                77.78(3)
_cell_angle_beta                 89.74(3)
_cell_angle_gamma                77.45(3)
_cell_formula_units_Z            2
_cell_length_a                   5.0825(10)
_cell_length_b                   9.7492(19)
_cell_length_c                   15.148(3)
_cell_measurement_reflns_used    2672
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      30.9295
_cell_measurement_theta_min      2.1918
_cell_volume                     715.4(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       'ω scans'
_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  0.0594
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9583
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9740
_exptl_absorpt_correction_T_min  0.9490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst. 1995 A51, 33-38'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.199
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0905
_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)+(0.1590P)²+0.2172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2628
_refine_ls_wR_factor_ref         0.2711
_reflns_number_gt                3205
_reflns_number_total             3440
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg501469r_si_002.cif
_cod_data_source_block           TG-NA
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4512287--4512291.cif.
;
_cod_original_cell_volume        715.4(2)
_cod_database_code               4512287
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
F1 F 0.3283(3) -0.14998(16) 0.51173(9) 0.0362(4) Uani 1 1 d .
N1 N 0.7257(4) -0.1316(2) 0.70283(12) 0.0288(4) Uani 1 1 d .
O1 O 0.8220(4) -0.28367(19) 0.60469(12) 0.0381(4) Uani 1 1 d .
O2 O 0.6326(3) 0.00813(17) 0.80778(10) 0.0324(4) Uani 1 1 d .
O4 O 0.8122(3) 0.7466(2) 1.03820(12) 0.0419(5) Uani 1 1 d .
N2 N 0.3288(4) 0.0489(2) 0.68769(12) 0.0288(4) Uani 1 1 d .
N4 N 0.2035(4) 0.7254(2) 0.80587(13) 0.0313(5) Uani 1 1 d .
O3 O -0.0933(3) 0.21617(17) 0.66884(11) 0.0332(4) Uani 1 1 d .
C3 C 0.2507(4) 0.0044(2) 0.61330(14) 0.0284(5) Uani 1 1 d .
H3 H 0.0844 0.0533 0.5817 0.034 Uiso 1 1 calc R
C2 C 0.4053(5) -0.1065(2) 0.58460(14) 0.0298(5) Uani 1 1 d .
C4 C 0.5664(4) -0.0224(2) 0.73725(14) 0.0275(5) Uani 1 1 d .
C13 C 0.2652(5) 0.7670(2) 0.88064(15) 0.0298(5) Uani 1 1 d .
H13 H 0.1418 0.8435 0.8984 0.036 Uiso 1 1 calc R
C10 C 0.6806(5) 0.5893(3) 0.90771(16) 0.0338(5) Uani 1 1 d .
H10 H 0.8448 0.5440 0.9416 0.041 Uiso 1 1 calc R
N3 N 0.3619(4) 0.8232(2) 1.05621(14) 0.0367(5) Uani 1 1 d .
C5 C 0.1473(4) 0.1691(2) 0.72271(14) 0.0294(5) Uani 1 1 d .
H5 H 0.1068 0.1337 0.7871 0.035 Uiso 1 1 calc R
C14 C 0.5731(5) 0.7588(3) 1.01461(15) 0.0325(5) Uani 1 1 d .
C8 C -0.0871(5) 0.3516(2) 0.60447(16) 0.0345(5) Uani 1 1 d .
H8A H -0.2268 0.4317 0.6179 0.041 Uiso 1 1 calc R
H8B H -0.1202 0.3428 0.5418 0.041 Uiso 1 1 calc R
C1 C 0.6671(4) -0.1832(2) 0.62848(14) 0.0283(5) Uani 1 1 d .
C11 C 0.6154(5) 0.5425(3) 0.83188(17) 0.0351(5) Uani 1 1 d .
H11 H 0.7315 0.4636 0.8141 0.042 Uiso 1 1 calc R
C9 C 0.5034(4) 0.7031(2) 0.93391(14) 0.0298(5) Uani 1 1 d .
C6 C 0.2737(4) 0.2990(2) 0.71446(15) 0.0307(5) Uani 1 1 d .
H6A H 0.4722 0.2695 0.7245 0.037 Uiso 1 1 calc R
H6B H 0.1980 0.3591 0.7576 0.037 Uiso 1 1 calc R
C12 C 0.3765(5) 0.6136(3) 0.78248(15) 0.0329(5) Uani 1 1 d .
H12 H 0.3332 0.5822 0.7302 0.039 Uiso 1 1 calc R
C7 C 0.1936(5) 0.3785(2) 0.61615(15) 0.0331(5) Uani 1 1 d .
H7A H 0.1885 0.4826 0.6076 0.040 Uiso 1 1 calc R
H7B H 0.3191 0.3376 0.5734 0.040 Uiso 1 1 calc R
H4 H 0.185(6) 0.815(3) 1.041(2) 0.041(8) Uiso 1 1 d .
H2 H 0.380(6) 0.855(4) 1.102(2) 0.045(8) Uiso 1 1 d .
H1 H 0.888(7) -0.179(4) 0.740(2) 0.051(9) Uiso 1 1 d .
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 N1 C1 127.52(19)
C4 N1 H1 112(2)
C1 N1 H1 120(2)
C3 N2 C4 121.07(18)
C3 N2 C5 121.08(18)
C4 N2 C5 117.65(18)
C13 N4 C12 118.0(2)
C5 O3 C8 109.72(17)
C2 C3 N2 121.3(2)
C2 C3 H3 119.4
N2 C3 H3 119.4
C3 C2 F1 121.2(2)
C3 C2 C1 122.0(2)
F1 C2 C1 116.79(19)
O2 C4 N1 121.7(2)
O2 C4 N2 122.7(2)
N1 C4 N2 115.67(19)
N4 C13 C9 123.2(2)
N4 C13 H13 118.4
C9 C13 H13 118.4
C11 C10 C9 119.6(2)
C11 C10 H10 120.2
C9 C10 H10 120.2
C14 N3 H4 119.0(19)
C14 N3 H2 123(2)
H4 N3 H2 117(3)
O3 C5 N2 108.60(17)
O3 C5 C6 106.46(17)
N2 C5 C6 111.56(17)
O3 C5 H5 110.0
N2 C5 H5 110.0
C6 C5 H5 110.0
O4 C14 N3 123.7(2)
O4 C14 C9 120.6(2)
N3 C14 C9 115.7(2)
O3 C8 C7 106.00(18)
O3 C8 H8A 110.5
C7 C8 H8A 110.5
O3 C8 H8B 110.5
C7 C8 H8B 110.5
H8A C8 H8B 108.7
O1 C1 N1 122.2(2)
O1 C1 C2 125.6(2)
N1 C1 C2 112.23(19)
C10 C11 C12 118.7(2)
C10 C11 H11 120.6
C12 C11 H11 120.6
C10 C9 C13 117.7(2)
C10 C9 C14 120.7(2)
C13 C9 C14 121.6(2)
C5 C6 C7 101.79(18)
C5 C6 H6A 111.4
C7 C6 H6A 111.4
C5 C6 H6B 111.4
C7 C6 H6B 111.4
H6A C6 H6B 109.3
N4 C12 C11 122.7(2)
N4 C12 H12 118.6
C11 C12 H12 118.6
C8 C7 C6 102.02(18)
C8 C7 H7A 111.4
C6 C7 H7A 111.4
C8 C7 H7B 111.4
C6 C7 H7B 111.4
H7A C7 H7B 109.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C2 1.351(3)
N1 C4 1.384(3)
N1 C1 1.385(3)
N1 H1 0.97(4)
O1 C1 1.233(3)
O2 C4 1.235(3)
O4 C14 1.242(3)
N2 C3 1.379(3)
N2 C4 1.389(3)
N2 C5 1.514(3)
N4 C13 1.341(3)
N4 C12 1.353(3)
O3 C5 1.407(3)
O3 C8 1.472(3)
C3 C2 1.343(3)
C3 H3 0.9500
C2 C1 1.462(3)
C13 C9 1.405(3)
C13 H13 0.9500
C10 C11 1.388(3)
C10 C9 1.396(3)
C10 H10 0.9500
N3 C14 1.346(3)
N3 H4 0.95(3)
N3 H2 0.83(4)
C5 C6 1.523(3)
C5 H5 1.0000
C14 C9 1.511(3)
C8 C7 1.523(3)
C8 H8A 0.9900
C8 H8B 0.9900
C11 C12 1.392(3)
C11 H11 0.9500
C6 C7 1.538(3)
C6 H6A 0.9900
C6 H6B 0.9900
C12 H12 0.9500
C7 H7A 0.9900
C7 H7B 0.9900
