#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/07/2220743.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_2220743
loop_
_publ_author_name
'Gainsford, Graeme J.'
'Clinch, Keith'
_publ_section_title
;
 3-Benzoyl-5-chlorouracil
;
_journal_coeditor_code           CI2757
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o342
_journal_paper_doi               10.1107/S1600536809001287
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H7 Cl N2 O3'
_chemical_formula_moiety         'C11 H7 Cl N2 O3'
_chemical_formula_sum            'C11 H7 Cl N2 O3'
_chemical_formula_weight         250.64
_chemical_name_systematic
;
3-Benzoyl-5-chloro-pyrimidine-2,4(1H,3H)-dione
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 113.169(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.9357(9)
_cell_length_b                   5.4020(2)
_cell_length_c                   19.9642(9)
_cell_measurement_reflns_used    6298
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.65
_cell_measurement_theta_min      2.22
_cell_volume                     2174.89(16)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics
;
ORTEP in WinGX (Farrugia, 1999) and Mercury (Bruno et al.,
2002)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Bruker--Nonius APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_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  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            24616
_diffrn_reflns_theta_full        29.01
_diffrn_reflns_theta_max         29.01
_diffrn_reflns_theta_min         3.54
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Blessing, 1995; Bruker, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.417
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0407
_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)+(0.0468P)²+2.9413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1100
_reflns_number_gt                2189
_reflns_number_total             2899
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2757.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      'C 2/c'
_cod_database_code               2220743
_cod_database_fobs_code          2220743
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, 1/2-z'
'-x, -y, -z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'1/2-x, 1/2+y, 1/2-z'
'1/2-x, 1/2-y, -z'
'1/2+ x, 1/2-y, 1/2+z'
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
Cl Cl16 0.72366(2) 0.47956(9) 0.28923(3) 0.03151(14) Uani d . 1 . .
O O14 0.68050(6) 1.0941(2) 0.50072(7) 0.0230(3) Uani d . 1 . .
O O15 0.61273(7) 0.4522(3) 0.34170(8) 0.0316(3) Uani d . 1 . .
O O17 0.60738(6) 0.5865(3) 0.49746(7) 0.0259(3) Uani d . 1 . .
N N1 0.73929(7) 1.0080(3) 0.43155(8) 0.0196(3) Uani d . 1 . .
H H1N 0.7670(11) 1.123(5) 0.4545(12) 0.034(6) Uiso d . 1 . .
N N3 0.64590(6) 0.7803(3) 0.41885(8) 0.0185(3) Uani d . 1 . .
C C2 0.68836(8) 0.9710(3) 0.45337(9) 0.0178(3) Uani d . 1 . .
C C4 0.65184(8) 0.6191(3) 0.36658(10) 0.0212(4) Uani d . 1 . .
C C5 0.70867(8) 0.6748(3) 0.34898(10) 0.0206(3) Uani d . 1 . .
C C6 0.74965(8) 0.8616(3) 0.38121(10) 0.0204(3) Uani d . 1 . .
H H6 0.7865(11) 0.905(4) 0.3704(11) 0.025(5) Uiso d . 1 . .
C C7 0.59307(8) 0.7215(3) 0.44632(10) 0.0189(3) Uani d . 1 . .
C C8 0.52873(8) 0.8413(3) 0.40703(10) 0.0204(4) Uani d . 1 . .
C C9 0.51969(9) 1.0174(4) 0.35368(11) 0.0280(4) Uani d . 1 . .
H H9 0.5554 1.0604 0.3403 0.034 Uiso calc R 1 . .
C C10 0.45871(10) 1.1310(4) 0.31977(12) 0.0367(5) Uani d . 1 . .
H H10 0.4524 1.2524 0.2832 0.044 Uiso calc R 1 . .
C C11 0.40709(10) 1.0666(5) 0.33943(13) 0.0398(5) Uani d . 1 . .
H H11 0.3650 1.1426 0.3156 0.048 Uiso calc R 1 . .
C C12 0.41587(10) 0.8944(5) 0.39288(14) 0.0458(6) Uani d . 1 . .
H H12 0.3800 0.8527 0.4061 0.055 Uiso calc R 1 . .
C C13 0.47664(10) 0.7816(4) 0.42752(13) 0.0375(5) Uani d . 1 . .
H H13 0.4830 0.6640 0.4651 0.045 Uiso calc R 1 . .
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 N1 C6 . . 122.97(15) ?
C2 N1 H1N . . 115.5(15) ?
C6 N1 H1N . . 121.3(15) ?
C2 N3 C4 . . 126.39(14) ?
C2 N3 C7 . . 116.31(14) ?
C4 N3 C7 . . 116.87(13) ?
O14 C2 N1 . . 123.34(15) ?
O14 C2 N3 . . 121.36(14) ?
N1 C2 N3 . . 115.29(15) ?
O15 C4 N3 . . 120.65(15) ?
O15 C4 C5 . . 126.35(17) ?
N3 C4 C5 . . 113.00(15) ?
C6 C5 C4 . . 121.21(16) ?
C6 C5 Cl16 . . 121.45(13) ?
C4 C5 Cl16 . . 117.23(13) ?
C5 C6 N1 . . 121.09(16) ?
C5 C6 H6 . . 123.4(13) ?
N1 C6 H6 . . 115.4(13) ?
O17 C7 C8 . . 126.97(15) ?
O17 C7 N3 . . 117.53(15) ?
C8 C7 N3 . . 115.49(14) ?
C9 C8 C13 . . 119.96(17) ?
C9 C8 C7 . . 122.09(15) ?
C13 C8 C7 . . 117.87(16) ?
C10 C9 C8 . . 120.02(17) ?
C10 C9 H9 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C11 C10 C9 . . 119.52(19) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
C12 C11 C10 . . 120.82(19) ?
C12 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
C11 C12 C13 . . 120.15(19) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C12 C13 C8 . . 119.51(19) ?
C12 C13 H13 . . 120.2 ?
C8 C13 H13 . . 120.2 ?
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
Cl16 C5 . 1.7179(18) ?
O14 C2 . 1.222(2) ?
O15 C4 . 1.209(2) ?
O17 C7 . 1.192(2) ?
N1 C2 . 1.364(2) ?
N1 C6 . 1.366(2) ?
N1 H1N . 0.87(3) ?
N3 C2 . 1.378(2) ?
N3 C4 . 1.404(2) ?
N3 C7 . 1.498(2) ?
C4 C5 . 1.453(2) ?
C5 C6 . 1.336(2) ?
C6 H6 . 0.94(2) ?
C7 C8 . 1.468(2) ?
C8 C9 . 1.383(3) ?
C8 C13 . 1.394(2) ?
C9 C10 . 1.382(3) ?
C9 H9 . 0.95 ?
C10 C11 . 1.381(3) ?
C10 H10 . 0.95 ?
C11 C12 . 1.371(3) ?
C11 H11 . 0.95 ?
C12 C13 . 1.379(3) ?
C12 H12 . 0.95 ?
C13 H13 . 0.95 ?
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
_geom_hbond_publ_flag
N1 H1N O14 7_676 0.86(3) 1.91(3) 2.770(2) 173(3) yes
C9 H9 O15 1_565 0.95 2.46 3.182(3) 133 yes
C10 H10 O15 2_665 0.95 2.57 3.447(3) 153 yes
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 N1 C2 O14 . . . . 176.60(17) ?
C6 N1 C2 N3 . . . . -2.5(2) ?
C4 N3 C2 O14 . . . . -176.59(17) ?
C7 N3 C2 O14 . . . . -4.3(2) ?
C4 N3 C2 N1 . . . . 2.6(2) ?
C7 N3 C2 N1 . . . . 174.86(14) ?
C2 N3 C4 O15 . . . . 177.38(17) ?
C7 N3 C4 O15 . . . . 5.1(3) ?
C2 N3 C4 C5 . . . . -1.5(2) ?
C7 N3 C4 C5 . . . . -173.75(15) ?
O15 C4 C5 C6 . . . . -178.47(19) ?
N3 C4 C5 C6 . . . . 0.3(3) ?
O15 C4 C5 Cl16 . . . . -2.2(3) ?
N3 C4 C5 Cl16 . . . . 176.58(12) ?
C4 C5 C6 N1 . . . . -0.4(3) ?
Cl16 C5 C6 N1 . . . . -176.52(14) ?
C2 N1 C6 C5 . . . . 1.6(3) ?
C2 N3 C7 O17 . . . . -84.6(2) ?
C4 N3 C7 O17 . . . . 88.4(2) ?
C2 N3 C7 C8 . . . . 94.63(18) ?
C4 N3 C7 C8 . . . . -92.32(19) ?
O17 C7 C8 C9 . . . . 172.27(19) ?
N3 C7 C8 C9 . . . . -6.9(3) ?
O17 C7 C8 C13 . . . . -4.6(3) ?
N3 C7 C8 C13 . . . . 176.25(18) ?
C13 C8 C9 C10 . . . . -1.2(3) ?
C7 C8 C9 C10 . . . . -177.94(19) ?
C8 C9 C10 C11 . . . . -0.2(4) ?
C9 C10 C11 C12 . . . . 1.0(4) ?
C10 C11 C12 C13 . . . . -0.4(4) ?
C11 C12 C13 C8 . . . . -0.9(4) ?
C9 C8 C13 C12 . . . . 1.7(4) ?
C7 C8 C13 C12 . . . . 178.6(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741578
