#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/42/2204297.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_2204297
loop_
_publ_author_name
'Hulme, Ashley T.'
'Tocher, Derek A.'
_publ_section_title
;
 5-Fluorouracil--1,4-dioxane (4/1)
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1781
_journal_page_last               o1782
_journal_paper_doi               10.1107/S1600536804022251
_journal_volume                  60
_journal_year                    2004
_chemical_formula_moiety         'C4 H8 O2, 4C4 H3 F N2 O2'
_chemical_formula_sum            'C20 H20 F4 N8 O10'
_chemical_formula_weight         608.44
_chemical_name_systematic
;
5-Fluorouracil 1,4-dioxane (4/1)
;
_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   'found from delta F'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.128(3)
_cell_angle_beta                 96.913(3)
_cell_angle_gamma                99.785(3)
_cell_formula_units_Z            1
_cell_length_a                   7.0847(11)
_cell_length_b                   8.4733(13)
_cell_length_c                   10.2291(15)
_cell_measurement_reflns_used    1082
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.6805
_cell_measurement_theta_min      2.4735
_cell_volume                     592.45(16)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.927
_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  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5320
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.9953
_exptl_absorpt_correction_T_min  0.9471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.325
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0457P)²+0.1655P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1142
_reflns_number_gt                2131
_reflns_number_total             2741
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ci6440.cif
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2204297
_cod_database_fobs_code          2204297
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_occupancy
_atom_site_type_symbol
F9 0.37304(19) 0.84841(15) 0.16434(12) 0.0278(3) Uani d 1 F
O7 0.0566(2) 0.69895(17) 0.59096(14) 0.0232(4) Uani d 1 O
O8 0.1991(2) 0.53627(17) 0.17616(14) 0.0234(4) Uani d 1 O
N1 0.2094(3) 0.8886(2) 0.48334(18) 0.0196(4) Uani d 1 N
H1 0.207(4) 0.966(3) 0.543(3) 0.035(7) Uiso d 1 H
N3 0.1319(2) 0.6192(2) 0.38430(16) 0.0172(4) Uani d 1 N
H3 0.075(3) 0.515(3) 0.389(2) 0.025(6) Uiso d 1 H
C2 0.1276(3) 0.7343(2) 0.4933(2) 0.0175(4) Uani d 1 C
C4 0.2065(3) 0.6469(2) 0.2685(2) 0.0172(4) Uani d 1 C
C5 0.2912(3) 0.8144(2) 0.2720(2) 0.0182(4) Uani d 1 C
C6 0.2897(3) 0.9295(3) 0.3745(2) 0.0206(5) Uani d 1 C
H6 0.341(3) 1.040(3) 0.377(2) 0.016(5) Uiso d 1 H
F19 0.47754(18) 0.80432(14) 0.86893(12) 0.0258(3) Uani d 1 F
O17 0.2285(2) 0.17889(17) 0.65744(14) 0.0222(4) Uani d 1 O
O18 0.5329(2) 0.68229(17) 0.61498(14) 0.0214(3) Uani d 1 O
N11 0.2653(2) 0.3825(2) 0.83458(16) 0.0162(4) Uani d 1 N
H11 0.203(3) 0.311(3) 0.881(2) 0.026(6) Uiso d 1 H
N13 0.3790(3) 0.4320(2) 0.63923(17) 0.0167(4) Uani d 1 N
H13 0.399(3) 0.398(3) 0.561(2) 0.021(6) Uiso d 1 H
C12 0.2873(3) 0.3209(2) 0.70817(19) 0.0158(4) Uani d 1 C
C14 0.4501(3) 0.5943(2) 0.6848(2) 0.0161(4) Uani d 1 C
C15 0.4153(3) 0.6458(2) 0.8187(2) 0.0169(4) Uani d 1 C
C16 0.3266(3) 0.5434(2) 0.8892(2) 0.0171(4) Uani d 1 C
H16 0.304(3) 0.576(3) 0.976(2) 0.020(6) Uiso d 1 H
O21 0.0777(2) 0.14345(17) 0.95410(15) 0.0241(4) Uani d 1 O
C21 0.1347(3) -0.0087(3) 0.9117(2) 0.0230(5) Uani d 1 C
H21A 0.162(3) -0.009(3) 0.819(2) 0.021(6) Uiso d 1 H
H21B 0.255(3) -0.013(3) 0.973(2) 0.021(6) Uiso d 1 H
C22 0.0271(4) 0.1472(3) 1.0864(2) 0.0237(5) Uani d 1 C
H22A 0.143(3) 0.138(3) 1.150(2) 0.031(7) Uiso d 1 H
H22B -0.012(3) 0.249(3) 1.109(2) 0.019(6) Uiso d 1 H
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 N1 C6 . . 123.56(18)
C2 N1 H1 . . 120.8(18)
C6 N1 H1 . . 115.6(18)
C2 N3 C4 . . 126.62(18)
C2 N3 H3 . . 115.6(15)
C4 N3 H3 . . 117.7(15)
O7 C2 N1 . . 123.09(19)
O7 C2 N3 . . 122.19(19)
N1 C2 N3 . . 114.72(18)
O8 C4 N3 . . 121.43(19)
O8 C4 C5 . . 125.64(19)
N3 C4 C5 . . 112.93(17)
C6 C5 F9 . . 121.62(18)
C6 C5 C4 . . 122.52(19)
F9 C5 C4 . . 115.86(17)
C5 C6 N1 . . 119.60(19)
C5 C6 H6 . . 123.6(13)
N1 C6 H6 . . 116.8(13)
C12 N11 C16 . . 122.96(17)
C12 N11 H11 . . 116.2(15)
C16 N11 H11 . . 120.8(14)
C14 N13 C12 . . 127.10(18)
C14 N13 H13 . . 115.1(15)
C12 N13 H13 . . 117.7(15)
O17 C12 N11 . . 123.41(18)
O17 C12 N13 . . 121.69(18)
N11 C12 N13 . . 114.89(17)
O18 C14 N13 . . 121.64(18)
O18 C14 C15 . . 125.45(18)
N13 C14 C15 . . 112.90(17)
C16 C15 F19 . . 121.57(18)
C16 C15 C14 . . 122.27(19)
F19 C15 C14 . . 116.16(17)
C15 C16 N11 . . 119.84(19)
C15 C16 H16 . . 122.7(14)
N11 C16 H16 . . 117.5(14)
C22 O21 C21 . . 109.42(16)
O21 C21 C22 . 2_557 110.12(18)
O21 C21 H21A . . 107.1(13)
C22 C21 H21A 2_557 . 109.0(13)
O21 C21 H21B . . 107.8(12)
C22 C21 H21B 2_557 . 112.2(12)
H21A C21 H21B . . 110.5(17)
O21 C22 C21 . 2_557 110.23(18)
O21 C22 H22A . . 109.5(14)
C21 C22 H22A 2_557 . 109.2(14)
O21 C22 H22B . . 106.3(13)
C21 C22 H22B 2_557 . 110.9(13)
H22A C22 H22B . . 110.6(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
F9 C5 . 1.349(2)
O7 C2 . 1.223(2)
O8 C4 . 1.223(2)
N1 C2 . 1.360(3)
N1 C6 . 1.371(3)
N1 H1 . 0.83(3)
N3 C2 . 1.380(3)
N3 C4 . 1.387(3)
N3 H3 . 0.91(2)
C4 C5 . 1.437(3)
C5 C6 . 1.330(3)
C6 H6 . 0.94(2)
F19 C15 . 1.346(2)
O17 C12 . 1.222(2)
O18 C14 . 1.230(2)
N11 C12 . 1.362(2)
N11 C16 . 1.372(3)
N11 H11 . 0.91(2)
N13 C14 . 1.374(3)
N13 C12 . 1.376(3)
N13 H13 . 0.85(2)
C14 C15 . 1.441(3)
C15 C16 . 1.330(3)
C16 H16 . 0.93(2)
O21 C22 . 1.439(2)
O21 C21 . 1.440(3)
C21 C22 2_557 1.499(3)
C21 H21A . 0.99(2)
C21 H21B . 1.00(2)
C22 C21 2_557 1.499(3)
C22 H22A . 1.00(2)
C22 H22B . 0.96(2)
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 O17 1_565 0.83(3) 1.98(3) 2.798(2) 167(2)
N3 H3 O7 2_566 0.91(2) 1.95(2) 2.857(2) 176(2)
N11 H11 O21 . 0.91(2) 1.84(2) 2.746(2) 171(2)
N13 H13 O18 2_666 0.85(2) 1.98(2) 2.824(2) 175(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_site_symmetry_4
_geom_torsion
C6 N1 C2 O7 . 179.8(2)
C6 N1 C2 N3 . 0.3(3)
C4 N3 C2 O7 . 179.2(2)
C4 N3 C2 N1 . -1.3(3)
C2 N3 C4 O8 . -178.30(19)
C2 N3 C4 C5 . 2.3(3)
O8 C4 C5 C6 . 178.1(2)
N3 C4 C5 C6 . -2.4(3)
O8 C4 C5 F9 . -1.8(3)
N3 C4 C5 F9 . 177.60(17)
F9 C5 C6 N1 . -178.30(19)
C4 C5 C6 N1 . 1.7(3)
C2 N1 C6 C5 . -0.6(3)
C16 N11 C12 O17 . -178.0(2)
C16 N11 C12 N13 . 1.0(3)
C14 N13 C12 O17 . 179.6(2)
C14 N13 C12 N11 . 0.7(3)
C12 N13 C14 O18 . 178.74(19)
C12 N13 C14 C15 . -1.7(3)
O18 C14 C15 C16 . -179.2(2)
N13 C14 C15 C16 . 1.3(3)
O18 C14 C15 F19 . 0.9(3)
N13 C14 C15 F19 . -178.66(17)
F19 C15 C16 N11 . -179.98(18)
C14 C15 C16 N11 . 0.1(3)
C12 N11 C16 C15 . -1.3(3)
C22 O21 C21 C22 2_557 58.7(3)
C21 O21 C22 C21 2_557 -58.8(3)
