#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/35/2223525.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_2223525
loop_
_publ_author_name
'Parrish, Damon'
'Glass, Brian'
'Rehberg, Gretchen M.'
'Kastner, Margaret E.'
_publ_section_title
;
 4,5-Dichloro-2H-1,3-oxazine-2,6(3H)-dione
;
_journal_coeditor_code           PV2198
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2356
_journal_paper_doi               10.1107/S1600536809034606
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C4 H Cl2 N O3'
_chemical_formula_moiety         'C4 H Cl2 N O3'
_chemical_formula_sum            'C4 H Cl2 N O3'
_chemical_formula_weight         181.96
_chemical_name_common            4,5-dichloro-3-oxauracil
_chemical_name_systematic
;
4,5-Dichloro-2H-1,3-oxazine-2,6(3H)-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.359(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2290(16)
_cell_length_b                   5.2549(8)
_cell_length_c                   12.2766(16)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10.
_cell_volume                     610.28(16)
_computing_cell_refinement       'XSCANS (Bruker, 1996)'
_computing_data_collection       'XSCANS (Bruker, 1996)'
_computing_data_reduction        'XSCANS (Bruker, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens R3m/V'
_diffrn_measurement_method       θ-2θ
_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  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0137
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            1566
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.996
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.980
_exptl_crystal_density_meas      1.92
_exptl_crystal_density_method    floatation
_exptl_crystal_description       plates
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.380
_refine_ls_extinction_coef       0.042(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1405
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0341
_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)+(0.0666P)²+0.3617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                1235
_reflns_number_total             1405
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2198.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223525
_cod_database_fobs_code          2223525
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_disorder_assembly
_atom_site_disorder_group
O O1 0.89484(14) 0.7547(3) 0.20549(12) 0.0405(4) Uani d . 1 . .
C C2 0.9358(2) 0.6588(4) 0.12050(17) 0.0362(4) Uani d . 1 . .
O O2 1.03514(16) 0.7544(3) 0.10600(14) 0.0474(4) Uani d . 1 . .
N N3 0.86084(17) 0.4586(3) 0.05845(14) 0.0363(4) Uani d . 1 . .
H H3 0.8864 0.3892 0.0062 0.044 Uiso calc R 1 . .
C C4 0.74604(19) 0.3625(3) 0.07572(15) 0.0325(4) Uani d . 1 . .
Cl Cl4 0.66660(6) 0.11274(10) -0.01234(4) 0.0453(2) Uani d . 1 . .
C C5 0.7009(2) 0.4611(4) 0.15609(16) 0.0347(4) Uani d . 1 . .
Cl Cl5 0.55557(6) 0.35198(11) 0.17764(5) 0.0491(2) Uani d . 1 . .
C C6 0.7780(2) 0.6694(4) 0.22914(17) 0.0366(4) Uani d . 1 . .
O O6 0.75456(18) 0.7746(3) 0.30575(15) 0.0533(4) Uani d . 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
O1 0.0479(8) 0.0401(8) 0.0369(7) -0.0084(6) 0.0199(6) -0.0094(6)
C2 0.0401(10) 0.0363(9) 0.0321(9) -0.0007(8) 0.0138(8) 0.0003(7)
O2 0.0479(8) 0.0484(9) 0.0515(9) -0.0126(7) 0.0251(7) -0.0079(7)
N3 0.0405(8) 0.0411(9) 0.0317(8) -0.0050(7) 0.0188(6) -0.0060(7)
C4 0.0366(9) 0.0333(9) 0.0256(8) -0.0020(7) 0.0097(7) 0.0002(7)
Cl4 0.0530(3) 0.0453(3) 0.0375(3) -0.0132(2) 0.0172(2) -0.0125(2)
C5 0.0387(9) 0.0387(10) 0.0286(8) -0.0019(8) 0.0148(7) 0.0005(7)
Cl5 0.0526(3) 0.0587(4) 0.0464(3) -0.0136(2) 0.0303(3) -0.0082(2)
C6 0.0442(10) 0.0362(9) 0.0317(9) -0.0008(8) 0.0171(8) -0.0007(7)
O6 0.0691(10) 0.0521(9) 0.0484(9) -0.0073(8) 0.0334(8) -0.0166(7)
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C2 O1 C6 . . 125.02(15) ?
O2 C2 N3 . . 124.69(18) ?
O2 C2 O1 . . 118.79(18) ?
N3 C2 O1 . . 116.51(16) ?
C2 N3 C4 . . 122.41(16) ?
C2 N3 H3 . . 118.8 ?
C4 N3 H3 . . 118.8 ?
C5 C4 N3 . . 121.82(17) ?
C5 C4 Cl4 . . 123.46(15) ?
N3 C4 Cl4 . . 114.72(14) ?
C4 C5 C6 . . 119.33(17) ?
C4 C5 Cl5 . . 123.23(15) ?
C6 C5 Cl5 . . 117.44(14) ?
O6 C6 O1 . . 117.20(18) ?
O6 C6 C5 . . 127.99(19) ?
O1 C6 C5 . . 114.81(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.360(2) ?
O1 C6 . 1.406(2) ?
C2 O2 . 1.206(2) ?
C2 N3 . 1.353(3) ?
N3 C4 . 1.367(2) ?
N3 H3 . 0.8600 ?
C4 C5 . 1.342(3) ?
C4 Cl4 . 1.698(2) ?
C5 C6 . 1.444(3) ?
C5 Cl5 . 1.706(2) ?
C6 O6 . 1.192(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
N3 H3 O2 3_765 0.86 1.99 2.845(2) 174.1
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 O1 C2 O2 . . . . 177.41(18) ?
C6 O1 C2 N3 . . . . -3.1(3) ?
O2 C2 N3 C4 . . . . -177.81(19) ?
O1 C2 N3 C4 . . . . 2.7(3) ?
C2 N3 C4 C5 . . . . -0.3(3) ?
C2 N3 C4 Cl4 . . . . 179.47(15) ?
N3 C4 C5 C6 . . . . -2.0(3) ?
Cl4 C4 C5 C6 . . . . 178.29(14) ?
N3 C4 C5 Cl5 . . . . 178.26(14) ?
Cl4 C4 C5 Cl5 . . . . -1.5(3) ?
C2 O1 C6 O6 . . . . -179.15(19) ?
C2 O1 C6 C5 . . . . 1.0(3) ?
C4 C5 C6 O6 . . . . -178.2(2) ?
Cl5 C5 C6 O6 . . . . 1.5(3) ?
C4 C5 C6 O1 . . . . 1.6(3) ?
Cl5 C5 C6 O1 . . . . -178.62(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743216
