#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/39/7203999.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7203999
loop_
_publ_author_name
'Plüg, Carsten'
'Wallfisch, Bianca'
'Gade Andersen, Heidi'
'Bernhardt, Paul V.'
'Baker, Lisa-Jane'
'Clark, George R.'
'Wah Wong, Ming'
'Wentrup, Curt'
_publ_section_title
;
 Mesoionic pyridopyrimidinylium and pyridooxazinylium olates and
 non-mesoionic pyridopyrimidinones. Structures in the solid state,
 solution, and matrices †
;
_journal_issue                   10
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              2096
_journal_paper_doi               10.1039/b003933k
_journal_year                    2000
_chemical_formula_sum            'C13 H10 N4 O'
_chemical_formula_weight         238.25
_chemical_name_systematic
; 
 ? 
;
_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                 100.670(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.868(3)
_cell_length_b                   8.7030(10)
_cell_length_c                   11.834(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_volume                     1100.0(5)
_computing_cell_refinement       'SET4 in CAD4'
_computing_data_collection       CAD4
_computing_data_reduction        XTAL3.2
_computing_molecular_graphics    PLATON
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2036
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.91
_diffrn_standards_interval_time  7200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_type   \y-scans
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0596P)²+0.1856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                1432
_reflns_number_total             1929
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b003933k.txt
_cod_data_source_block           1617ha1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.1856P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.1856P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 2 1 / c'
_cod_database_code               7203999
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.30538(13) -0.17127(16) 1.10261(11) 0.0401(4) Uani 1 d . . .
C2 C 0.25622(14) -0.25903(18) 1.00981(13) 0.0352(4) Uani 1 d . . .
N2 N 0.22536(13) -0.40258(15) 1.04308(11) 0.0413(4) Uani 1 d . . .
H2 H 0.2376 -0.4174 1.1200 0.050 Uiso 1 d R . .
C3 C 0.24198(16) -0.2070(2) 0.89811(14) 0.0409(4) Uani 1 d . . .
H3 H 0.2069 -0.2714 0.8380 0.049 Uiso 1 calc R . .
C4 C 0.27933(15) -0.0596(2) 0.87403(13) 0.0390(4) Uani 1 d . . .
O4 O 0.27349(13) 0.00203(14) 0.77898(10) 0.0530(4) Uani 1 d . . .
N5 N 0.33369(12) 0.02941(15) 0.97399(11) 0.0358(3) Uani 1 d . . .
C6 C 0.37717(16) 0.1746(2) 0.95670(16) 0.0433(4) Uani 1 d . . .
H6 H 0.3684 0.2130 0.8823 0.052 Uiso 1 calc R . .
C7 C 0.43193(17) 0.2614(2) 1.04556(16) 0.0487(5) Uani 1 d . . .
H7 H 0.4619 0.3587 1.0327 0.058 Uiso 1 calc R . .
C8 C 0.44368(18) 0.2044(2) 1.15827(16) 0.0510(5) Uani 1 d . . .
H8 H 0.4827 0.2633 1.2202 0.061 Uiso 1 calc R . .
C9 C 0.39820(18) 0.0643(2) 1.17618(15) 0.0477(5) Uani 1 d . . .
H9 H 0.4030 0.0291 1.2511 0.057 Uiso 1 calc R . .
C10 C 0.34310(15) -0.03076(19) 1.08310(13) 0.0365(4) Uani 1 d . . .
C11 C 0.16285(15) -0.52278(18) 0.97963(13) 0.0376(4) Uani 1 d . . .
C12 C 0.12456(16) -0.6463(2) 1.03895(15) 0.0436(4) Uani 1 d . . .
H12 H 0.1407 -0.6482 1.1189 0.052 Uiso 1 calc R . .
C13 C 0.06259(17) -0.7651(2) 0.97740(17) 0.0505(5) Uani 1 d . . .
H13 H 0.0362 -0.8491 1.0152 0.061 Uiso 1 calc R . .
C14 C 0.03968(19) -0.7594(2) 0.85945(18) 0.0582(6) Uani 1 d . . .
H14 H -0.0026 -0.8384 0.8157 0.070 Uiso 1 calc R . .
C15 C 0.0808(2) -0.6348(2) 0.80916(17) 0.0664(6) Uani 1 d . . .
H15 H 0.0652 -0.6312 0.7292 0.080 Uiso 1 calc R . .
N3 N 0.14213(17) -0.51616(17) 0.86565(12) 0.0567(5) Uani 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C2 117.71(14) . . ?
N1 C2 N2 111.09(13) . . ?
N1 C2 C3 123.12(15) . . ?
N2 C2 C3 125.79(15) . . ?
C2 N2 C11 130.72(14) . . ?
C2 N2 H2 114.9 . . ?
C11 N2 H2 113.8 . . ?
C2 C3 C4 120.93(15) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
O4 C4 C3 128.21(15) . . ?
O4 C4 N5 117.12(15) . . ?
C3 C4 N5 114.66(14) . . ?
C6 N5 C10 121.28(14) . . ?
C6 N5 C4 118.00(14) . . ?
C10 N5 C4 120.71(14) . . ?
C7 C6 N5 120.99(16) . . ?
C7 C6 H6 119.5 . . ?
N5 C6 H6 119.5 . . ?
C6 C7 C8 119.60(17) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 119.79(17) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 121.34(17) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
N1 C10 N5 122.84(14) . . ?
N1 C10 C9 120.21(15) . . ?
N5 C10 C9 116.94(15) . . ?
N3 C11 C12 122.48(15) . . ?
N3 C11 N2 119.38(15) . . ?
C12 C11 N2 118.15(15) . . ?
C13 C12 C11 118.67(17) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C14 119.54(19) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 117.65(18) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
N3 C15 C14 124.98(19) . . ?
N3 C15 H15 117.5 . . ?
C14 C15 H15 117.5 . . ?
C11 N3 C15 116.69(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C10 1.324(2) . ?
N1 C2 1.363(2) . ?
C2 N2 1.370(2) . ?
C2 C3 1.379(2) . ?
N2 C11 1.390(2) . ?
N2 H2 0.9048 . ?
C3 C4 1.391(2) . ?
C3 H3 0.9300 . ?
C4 O4 1.2373(19) . ?
C4 N5 1.446(2) . ?
N5 C6 1.377(2) . ?
N5 C10 1.380(2) . ?
C6 C7 1.342(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.406(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.348(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.418(2) . ?
C9 H9 0.9300 . ?
C11 N3 1.327(2) . ?
C11 C12 1.389(2) . ?
C12 C13 1.368(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.352(3) . ?
C14 H14 0.9300 . ?
C15 N3 1.339(2) . ?
C15 H15 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O4 0.93 2.34 2.659(2) 99.8 .
N2 H2 O4 0.90 1.99 2.877(2) 166.0 4_556
C3 H3 N3 0.93 2.29 2.900(2) 123.1 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10197738
