#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/47/2014725.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_2014725
loop_
_publ_author_name
'Bortoluzzi, Adailton J.'
'Joussef, Antonio C.'
'Silva, Luiz E.'
'Rebelo, Ricardo A.'
_publ_section_title
;
 4,5,6,8,9-Pentachloropyrimido[1,2-a][1,8]naphthyridin-10-one
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o1
_journal_page_last               o3
_journal_paper_doi               10.1107/S0108270104031713
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C11 H2 Cl5 N3 O'
_chemical_formula_moiety         'C11 H2 Cl5 N3 O'
_chemical_formula_sum            'C11 H2 Cl5 N3 O'
_chemical_formula_weight         369.41
_chemical_name_systematic
;
4,5,6,8,9-Pentachloropyrimido[1,2a][1,8]naphthyridin-10-one
;
_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                 107.26(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.453(3)
_cell_length_b                   7.1730(10)
_cell_length_c                   22.368(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      14.01
_cell_measurement_theta_min      10.03
_cell_volume                     2520.9(7)
_computing_cell_refinement
;
SET4 in CAD4 EXPRESS
;
_computing_data_collection       'CAD4-EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'HELENA (Spek, 1996)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997)
;
_computing_publication_material
;
SHELXL97
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4 diffractometer'
_diffrn_measurement_method       ω--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  0.0888
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4607
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         1.30
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.145
_exptl_absorpt_correction_T_max  0.7766
_exptl_absorpt_correction_T_min  0.5973
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.406
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0353
_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)+(0.0703P)²+2.546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1113
_reflns_number_gt                3857
_reflns_number_total             4476
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk1788.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014725
_cod_database_fobs_code          2014725
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_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
_atom_site_type_symbol
C1A 0.75977(17) 0.7134(4) 0.56516(13) 0.0176(5) Uani d . 1 . . C
C2 0.90251(18) 0.6646(4) 0.60516(14) 0.0245(6) Uani d . 1 . . C
H2 0.9524 0.6660 0.6400 0.029 Uiso calc R 1 . . H
C3 0.91034(18) 0.6200(4) 0.54716(14) 0.0242(6) Uani d . 1 . . C
H3 0.9645 0.5924 0.5423 0.029 Uiso calc R 1 . . H
C4 0.83810(18) 0.6160(4) 0.49616(13) 0.0211(6) Uani d . 1 . . C
C4A 0.75803(17) 0.6707(4) 0.50275(12) 0.0179(6) Uani d . 1 . . C
C5 0.67701(18) 0.6784(4) 0.45435(12) 0.0205(6) Uani d . 1 . . C
C6 0.60410(17) 0.7005(4) 0.47013(12) 0.0196(6) Uani d . 1 . . C
C6A 0.60449(17) 0.7389(4) 0.53376(13) 0.0196(6) Uani d . 1 . . C
C8 0.53175(18) 0.8082(4) 0.60275(14) 0.0234(6) Uani d . 1 . . C
C9 0.60317(18) 0.8618(4) 0.64815(13) 0.0218(6) Uani d . 1 . . C
C10 0.68507(17) 0.8530(4) 0.63736(12) 0.0197(6) Uani d . 1 . . C
N1 0.82829(14) 0.7057(3) 0.61462(11) 0.0215(5) Uani d . 1 . . N
N7 0.53147(15) 0.7565(4) 0.54511(11) 0.0240(5) Uani d . 1 . . N
N10A 0.68302(14) 0.7648(3) 0.57859(10) 0.0179(5) Uani d . 1 . . N
O1 0.74979(12) 0.9158(3) 0.67339(9) 0.0258(5) Uani d . 1 . . O
Cl1 0.85216(5) 0.53137(12) 0.42775(3) 0.0303(2) Uani d . 1 . . Cl
Cl2 0.66924(5) 0.66533(13) 0.37632(3) 0.0329(2) Uani d . 1 . . Cl
Cl3 0.50657(4) 0.69676(11) 0.41527(3) 0.02813(19) Uani d . 1 . . Cl
Cl4 0.43414(5) 0.81213(14) 0.61592(4) 0.0369(2) Uani d . 1 . . Cl
Cl5 0.60123(5) 0.95300(11) 0.71853(3) 0.02978(19) Uani d . 1 . . Cl
C11A 0.07727(17) 0.7403(4) 0.30104(12) 0.0177(5) Uani d . 1 . . C
C12 -0.06641(18) 0.7132(4) 0.26181(13) 0.0230(6) Uani d . 1 . . C
H12 -0.1150 0.6736 0.2293 0.028 Uiso calc R 1 . . H
C13 -0.07854(17) 0.7903(4) 0.31505(13) 0.0211(6) Uani d . 1 . . C
H13 -0.1344 0.8114 0.3177 0.025 Uiso calc R 1 . . H
C14 -0.00813(18) 0.8365(4) 0.36449(12) 0.0193(6) Uani d . 1 . . C
C14A 0.07479(17) 0.8033(4) 0.36041(12) 0.0177(6) Uani d . 1 . . C
C15 0.15543(17) 0.8095(4) 0.41023(12) 0.0198(6) Uani d . 1 . . C
C16 0.22768(17) 0.7500(4) 0.39953(12) 0.0191(6) Uani d . 1 . . C
C16A 0.23084(17) 0.6974(4) 0.33785(13) 0.0179(6) Uani d . 1 . . C
C18 0.30526(17) 0.6132(4) 0.27137(13) 0.0208(6) Uani d . 1 . . C
C19 0.23984(18) 0.6529(4) 0.21984(13) 0.0207(6) Uani d . 1 . . C
C20 0.16181(17) 0.7304(4) 0.22555(12) 0.0198(6) Uani d . 1 . . C
N11 0.01005(15) 0.6918(4) 0.25380(11) 0.0209(5) Uani d . 1 . . N
N17 0.30359(15) 0.6425(4) 0.33061(11) 0.0223(5) Uani d . 1 . . N
N20A 0.15679(14) 0.7166(3) 0.28922(10) 0.0181(5) Uani d . 1 . . N
O2 0.10672(12) 0.8050(3) 0.18439(9) 0.0271(5) Uani d . 1 . . O
Cl6 -0.02940(5) 0.93633(13) 0.42822(3) 0.0336(2) Uani d . 1 . . Cl
Cl7 0.16148(4) 0.88150(11) 0.48464(3) 0.02616(18) Uani d . 1 . . Cl
Cl8 0.32331(4) 0.74718(11) 0.45735(3) 0.02521(18) Uani d . 1 . . Cl
Cl9 0.40059(4) 0.53309(12) 0.26428(3) 0.0308(2) Uani d . 1 . . Cl
Cl10 0.24718(5) 0.63364(12) 0.14515(3) 0.0305(2) Uani d . 1 . . Cl
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
_geom_angle_publ_flag
N1 C1A C4A 125.1(3) ?
N1 C1A N10A 114.9(2) ?
C4A C1A N10A 120.0(2) ?
N1 C2 C3 123.1(3) ?
N1 C2 H2 118.4 ?
C3 C2 H2 118.4 ?
C2 C3 C4 118.9(3) ?
C2 C3 H3 120.5 ?
C4 C3 H3 120.5 ?
C3 C4 C4A 120.3(3) ?
C3 C4 Cl1 115.5(2) ?
C4A C4 Cl1 124.1(2) ?
C1A C4A C4 114.3(2) y
C1A C4A C5 118.2(2) y
C4 C4A C5 127.5(2) y
C6 C5 C4A 119.9(2) ?
C6 C5 Cl2 117.8(2) ?
C4A C5 Cl2 122.2(2) ?
C5 C6 C6A 122.1(2) ?
C5 C6 Cl3 121.8(2) ?
C6A C6 Cl3 116.0(2) ?
N7 C6A N10A 123.9(3) y
N7 C6A C6 118.3(2) y
N10A C6A C6 117.8(2) y
N7 C8 C9 123.5(3) ?
N7 C8 Cl4 115.7(2) ?
C9 C8 Cl4 120.8(2) ?
C8 C9 C10 120.4(3) ?
C8 C9 Cl5 123.1(2) ?
C10 C9 Cl5 116.4(2) ?
O1 C10 C9 123.5(3) ?
O1 C10 N10A 122.9(2) ?
C9 C10 N10A 113.6(2) ?
C1A N1 C2 118.0(2) y
C6A N7 C8 118.2(2) y
C6A N10A C1A 120.2(2) y
C6A N10A C10 118.5(2) y
C1A N10A C10 121.2(2) y
N11 C11A C14A 125.5(2) ?
N11 C11A N20A 114.6(2) ?
C14A C11A N20A 119.9(2) ?
N11 C12 C13 123.1(3) ?
N11 C12 H12 118.4 ?
C13 C12 H12 118.4 ?
C12 C13 C14 119.0(3) ?
C12 C13 H13 120.5 ?
C14 C13 H13 120.5 ?
C13 C14 C14A 120.2(2) ?
C13 C14 Cl6 115.7(2) ?
C14A C14 Cl6 124.1(2) ?
C14 C14A C11A 114.3(2) ?
C14 C14A C15 128.4(2) ?
C11A C14A C15 117.0(2) ?
C16 C15 C14A 120.3(2) ?
C16 C15 Cl7 117.8(2) ?
C14A C15 Cl7 121.9(2) ?
C15 C16 C16A 122.3(2) ?
C15 C16 Cl8 122.0(2) ?
C16A C16 Cl8 115.6(2) ?
N17 C16A N20A 123.8(2) ?
N17 C16A C16 119.2(2) ?
N20A C16A C16 117.0(2) ?
N17 C18 C19 124.1(3) ?
N17 C18 Cl9 115.3(2) ?
C19 C18 Cl9 120.5(2) ?
C18 C19 C20 120.7(2) ?
C18 C19 Cl10 123.0(2) ?
C20 C19 Cl10 116.1(2) ?
O2 C20 C19 126.2(2) ?
O2 C20 N20A 121.9(2) ?
C19 C20 N20A 111.8(2) ?
C11A N11 C12 117.4(2) y
C16A N17 C18 116.9(2) y
C16A N20A C11A 120.8(2) y
C16A N20A C20 119.1(2) y
C11A N20A C20 119.8(2) y
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
C1A N1 . 1.326(4) ?
C1A C4A . 1.421(4) ?
C1A N10A . 1.430(4) y
C2 N1 . 1.333(4) ?
C2 C3 . 1.379(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.382(4) ?
C3 H3 . 0.9500 ?
C4 C4A . 1.423(4) ?
C4 Cl1 . 1.724(3) ?
C4A C5 . 1.448(4) ?
C5 C6 . 1.357(4) ?
C5 Cl2 . 1.714(3) ?
C6 C6A . 1.448(4) ?
C6 Cl3 . 1.707(3) ?
C6A N7 . 1.306(4) y
C6A N10A . 1.393(3) y
C8 N7 . 1.340(4) y
C8 C9 . 1.361(4) ?
C8 Cl4 . 1.717(3) ?
C9 C10 . 1.439(4) ?
C9 Cl5 . 1.714(3) ?
C10 O1 . 1.215(3) ?
C10 N10A . 1.450(4) y
C11A N11 . 1.329(4) ?
C11A C14A . 1.415(4) ?
C11A N20A . 1.420(3) y
C12 N11 . 1.331(4) ?
C12 C13 . 1.380(4) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.384(4) ?
C13 H13 . 0.9500 ?
C14 C14A . 1.414(4) ?
C14 Cl6 . 1.721(3) ?
C14A C15 . 1.458(4) ?
C15 C16 . 1.350(4) ?
C15 Cl7 . 1.717(3) ?
C16 C16A . 1.446(4) ?
C16 Cl8 . 1.715(3) ?
C16A N17 . 1.315(4) y
C16A N20A . 1.378(3) y
C18 N17 . 1.350(4) y
C18 C19 . 1.354(4) ?
C18 Cl9 . 1.721(3) ?
C19 C20 . 1.439(4) ?
C19 Cl10 . 1.716(3) ?
C20 O2 . 1.209(3) ?
C20 N20A . 1.454(3) ?
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
C2 H2 O2 4_676 0.95 2.45 3.308(3) 151
C12 H12 O1 4_475 0.95 2.30 3.219(3) 164
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28550955
