#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/19/2201932.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_2201932
loop_
_publ_author_name
'Wolska, Irena'
'Herold, Franciszek'
'Maj, Marta'
_publ_section_title
;
 4-(2-Pyridyl)-1H,2H-pyrido[1,2-c]pyrimidine-1,3-dione
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o511
_journal_page_last               o513
_journal_paper_doi               10.1107/S1600536803004999
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C13 H9 N3 O2'
_chemical_formula_moiety         'C13 H9 N3 O2'
_chemical_formula_sum            'C13 H9 N3 O2'
_chemical_formula_weight         239.23
_chemical_name_systematic
;
4-(2-pyridyl)-1H,3H-pyrido[1,2-c]pyrimidine-1,3-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                 103.51(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.631(2)
_cell_length_b                   8.041(2)
_cell_length_c                   16.054(3)
_cell_measurement_reflns_used    5139
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.121
_cell_measurement_theta_min      1.990
_cell_volume                     1083.3(4)
_computing_cell_refinement       'CrysAlisRED (Kuma, 2001)'
_computing_data_collection       'CrysAlisCCD (Kuma, 2001)'
_computing_data_reduction        CrysAlisRED
_computing_molecular_graphics    'Stereochemical Workstation (Siemens, 1989)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Kuma KM-4 CCD'
_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  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6578
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.64
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.225
_refine_ls_extinction_coef       0.079(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2608
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0711P)²+0.2921P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1271
_reflns_number_gt                2374
_reflns_number_total             2608
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6173.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2201932
_cod_database_fobs_code          2201932
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
C1 0.66728(14) 0.37519(16) 0.02778(7) 0.0300(3) Uani d . 1 . . C
N2 0.81401(12) 0.44383(14) 0.03738(6) 0.0319(3) Uani d . 1 . . N
H2 0.8434(18) 0.464(2) -0.0114(11) 0.038(4) Uiso d . 1 . . H
C3 0.92808(14) 0.46936(17) 0.11354(7) 0.0310(3) Uani d . 1 . . C
C4 0.88079(13) 0.42448(15) 0.19022(7) 0.0270(3) Uani d . 1 . . C
C4a 0.73298(13) 0.35177(14) 0.18474(7) 0.0251(2) Uani d . 1 . . C
C5 0.68228(15) 0.28362(16) 0.25680(7) 0.0316(3) Uani d . 1 . . C
H5 0.7501 0.2907 0.3110 0.041(4) Uiso calc R 1 . . H
C6 0.53887(16) 0.20962(18) 0.24799(8) 0.0382(3) Uani d . 1 . . C
H6 0.5106 0.1641 0.2956 0.049(5) Uiso calc R 1 . . H
C7 0.43085(15) 0.20087(19) 0.16639(9) 0.0393(3) Uani d . 1 . . C
H7 0.3304 0.1540 0.1606 0.056(5) Uiso calc R 1 . . H
C8 0.47598(14) 0.26122(18) 0.09789(8) 0.0342(3) Uani d . 1 . . C
H8 0.4059 0.2555 0.0443 0.045(4) Uiso calc R 1 . . H
N9 0.62590(11) 0.33244(13) 0.10541(6) 0.0275(2) Uani d . 1 . . N
O10 0.57679(11) 0.34905(14) -0.04136(6) 0.0416(3) Uani d . 1 . . O
O11 1.05933(11) 0.52654(16) 0.10936(6) 0.0468(3) Uani d . 1 . . O
C1' 0.99499(13) 0.44937(15) 0.27416(7) 0.0267(3) Uani d . 1 . . C
C2' 1.14888(15) 0.38492(18) 0.29000(8) 0.0360(3) Uani d . 1 . . C
H2' 1.1833 0.3273 0.2474 0.051(5) Uiso calc R 1 . . H
C3' 1.25007(16) 0.40770(19) 0.36993(9) 0.0414(3) Uani d . 1 . . C
H3' 1.3526 0.3638 0.3822 0.058(5) Uiso calc R 1 . . H
C4' 1.19598(17) 0.49666(18) 0.43100(8) 0.0400(3) Uani d . 1 . . C
H4' 1.2610 0.5138 0.4853 0.053(5) Uiso calc R 1 . . H
C5' 1.04281(17) 0.55966(17) 0.40952(8) 0.0362(3) Uani d . 1 . . C
H5' 1.0077 0.6214 0.4505 0.044(4) Uiso calc R 1 . . H
N6' 0.94195(12) 0.53711(13) 0.33324(6) 0.0310(3) Uani d . 1 . . N
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O10 C1 N2 123.84(11)
O10 C1 N9 121.36(11)
N2 C1 N9 114.79(10)
C1 N2 C3 127.49(10)
C1 N2 H2 114.9(10)
C3 N2 H2 117.2(10)
O11 C3 N2 118.32(10)
O11 C3 C4 126.06(11)
N2 C3 C4 115.62(10)
C4a C4 C3 119.65(10)
C4a C4 C1' 121.32(10)
C3 C4 C1' 118.97(10)
C4 C4a N9 120.50(10)
C4 C4a C5 123.91(10)
N9 C4a C5 115.49(10)
C6 C5 C4a 121.83(11)
C6 C5 H5 119.1
C4a C5 H5 119.1
C5 C6 C7 120.41(11)
C5 C6 H6 119.8
C7 C6 H6 119.8
C8 C7 C6 118.98(11)
C8 C7 H7 120.5
C6 C7 H7 120.5
C7 C8 N9 121.30(12)
C7 C8 H8 119.4
N9 C8 H8 119.4
C8 N9 C4a 121.85(10)
C8 N9 C1 116.31(10)
C4a N9 C1 121.74(9)
N6' C1' C2' 122.24(11)
N6' C1' C4 116.57(10)
C2' C1' C4 121.19(10)
C3' C2' C1' 119.20(12)
C3' C2' H2' 120.4
C1' C2' H2' 120.4
C4' C3' C2' 118.81(12)
C4' C3' H3' 120.6
C2' C3' H3' 120.6
C3' C4' C5' 118.38(12)
C3' C4' H4' 120.8
C5' C4' H4' 120.8
N6' C5' C4' 123.93(12)
N6' C5' H5' 118.0
C4' C5' H5' 118.0
C5' N6' C1' 117.41(10)
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
C1 O10 . 1.2171(15) yes
C1 N2 . 1.3568(16) ?
C1 N9 . 1.4166(15) ?
N2 C3 . 1.3943(16) ?
N2 H2 . 0.892(17) ?
C3 O11 . 1.2388(15) yes
C3 C4 . 1.4307(16) ?
C4 C4a . 1.3873(15) yes
C4 C1' . 1.4856(16) ?
C4a N9 . 1.3966(14) ?
C4a C5 . 1.4377(15) yes
C5 C6 . 1.3506(18) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.421(2) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.3403(19) ?
C7 H7 . 0.9300 ?
C8 N9 . 1.3942(15) ?
C8 H8 . 0.9300 ?
C1' N6' . 1.3452(15) ?
C1' C2' . 1.3928(17) ?
C2' C3' . 1.3854(18) ?
C2' H2' . 0.9300 ?
C3' C4' . 1.380(2) ?
C3' H3' . 0.9300 ?
C4' C5' . 1.382(2) ?
C4' H4' . 0.9300 ?
C5' N6' . 1.3388(16) ?
C5' H5' . 0.9300 ?
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
C5 H5 N6' . 0.93 2.55 3.0658(18) 115
N2 H2 O11 3_765 0.892(17) 1.950(17) 2.8293(15) 168.4(15)
C5 H5 O11 2_745 0.93 2.81 3.4095(18) 124
C2' H2' N6' 2_745 0.93 2.76 3.4097(18) 127
C6 H6 O10 4_566 0.93 2.55 3.3539(17) 145
C7 H7 N6' 2_645 0.93 2.55 3.4780(18) 172
C3' H3' O10 4_666 0.93 2.66 3.5165(19) 154
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
O10 C1 N2 C3 -176.11(13)
N9 C1 N2 C3 2.97(19)
C1 N2 C3 O11 176.41(13)
C1 N2 C3 C4 -3.10(19)
O11 C3 C4 C4a -175.89(13)
N2 C3 C4 C4a 3.57(18)
O11 C3 C4 C1' 1.1(2)
N2 C3 C4 C1' -179.42(11)
C3 C4 C4a N9 -4.36(17)
C1' C4 C4a N9 178.70(10)
C3 C4 C4a C5 171.99(11)
C1' C4 C4a C5 -4.95(18)
C4 C4a C5 C6 -178.03(12)
N9 C4a C5 C6 -1.52(18)
C4a C5 C6 C7 -1.7(2)
C5 C6 C7 C8 2.6(2)
C6 C7 C8 N9 -0.2(2)
C7 C8 N9 C4a -3.2(2)
C7 C8 N9 C1 173.25(13)
C4 C4a N9 C8 -179.42(11)
C5 C4a N9 C8 3.94(16)
C4 C4a N9 C1 4.34(17)
C5 C4a N9 C1 -172.30(11)
O10 C1 N9 C8 -0.75(18)
N2 C1 N9 C8 -179.86(11)
O10 C1 N9 C4a 175.68(11)
N2 C1 N9 C4a -3.43(17)
C4a C4 C1' N6' -56.11(16)
C3 C4 C1' N6' 126.93(12)
C4a C4 C1' C2' 124.05(13)
C3 C4 C1' C2' -52.91(17)
N6' C1' C2' C3' 1.7(2)
C4 C1' C2' C3' -178.43(12)
C1' C2' C3' C4' -1.3(2)
C2' C3' C4' C5' -0.2(2)
C3' C4' C5' N6' 1.3(2)
C4' C5' N6' C1' -0.84(19)
C2' C1' N6' C5' -0.69(18)
C4 C1' N6' C5' 179.47(10)
