#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/39/7203995.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_7203995
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            'C14 H10 N2 O2'
_chemical_formula_weight         238.24
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.2600(10)
_cell_angle_beta                 101.0860(10)
_cell_angle_gamma                101.8710(10)
_cell_formula_units_Z            2
_cell_length_a                   6.52870(10)
_cell_length_b                   7.30040(10)
_cell_length_c                   12.07350(10)
_cell_measurement_reflns_used    4409
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.90
_cell_volume                     542.483(13)
_computing_cell_refinement       'Siemens SMART (Siemens, 1994a)'
_computing_data_collection       'Siemens SMART (Siemens, 1994a)'
_computing_data_reduction        'Siemens SHELXTL (Siemens, 1994b)'
_computing_molecular_graphics    'Siemens SHELXTL (Siemens, 1994b)'
_computing_publication_material  'Siemens SHELXTL (Siemens, 1994b)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.894
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       'ω scans'
_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  0.0134
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2396
_diffrn_reflns_theta_full        28.21
_diffrn_reflns_theta_max         28.21
_diffrn_reflns_theta_min         2.90
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.9489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0660P)²+0.0657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1062
_reflns_number_gt                2074
_reflns_number_total             2396
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b003933k.txt
_cod_data_source_block           olate
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0660P)^2^+0.0657P] 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^)+(0.0660P)^2^+0.0657P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        542.482(12)
_cod_database_code               7203995
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N5 N 0.44237(13) 0.70468(12) 0.06193(7) 0.0229(2) Uani 1 d . . .
O2 O 0.80912(11) 0.96997(12) -0.12774(6) 0.0288(2) Uani 1 d . . .
C6 C 0.31796(18) 0.62897(16) 0.13204(10) 0.0279(2) Uani 1 d . . .
H6 H 0.172(2) 0.587(2) 0.0980(12) 0.038(4) Uiso 1 d . . .
N1 N 0.77046(14) 0.85365(13) 0.03134(7) 0.0248(2) Uani 1 d . . .
H1 H 0.915(3) 0.912(2) 0.0618(13) 0.043(4) Uiso 1 d . . .
O4 O 0.13803(12) 0.62955(13) -0.08250(7) 0.0362(2) Uani 1 d . . .
C7 C 0.40966(19) 0.61769(17) 0.24080(10) 0.0312(3) Uani 1 d . . .
H7 H 0.319(2) 0.564(2) 0.2852(12) 0.041(4) Uiso 1 d . . .
C8 C 0.6345(2) 0.68213(18) 0.28164(10) 0.0327(3) Uani 1 d . . .
H8 H 0.702(3) 0.668(2) 0.3602(14) 0.050(4) Uiso 1 d . . .
C9 C 0.75697(18) 0.75911(17) 0.21298(9) 0.0291(3) Uani 1 d . . .
H9 H 0.909(2) 0.805(2) 0.2352(12) 0.034(3) Uiso 1 d . . .
C10 C 0.65805(16) 0.77347(14) 0.10094(9) 0.0235(2) Uani 1 d . . .
C2 C 0.68316(16) 0.87599(15) -0.07948(9) 0.0229(2) Uani 1 d . . .
C3 C 0.45999(16) 0.79117(15) -0.12627(9) 0.0225(2) Uani 1 d . . .
C4 C 0.33042(17) 0.70508(15) -0.05785(9) 0.0249(2) Uani 1 d . . .
C11 C 0.36159(16) 0.78968(15) -0.24843(9) 0.0239(2) Uani 1 d . . .
C12 C 0.48678(18) 0.79781(18) -0.33055(10) 0.0324(3) Uani 1 d . . .
H12 H 0.643(2) 0.807(2) -0.3076(12) 0.042(4) Uiso 1 d . . .
C13 C 0.3967(2) 0.7935(2) -0.44473(11) 0.0434(3) Uani 1 d . . .
H13 H 0.492(3) 0.801(2) -0.4988(13) 0.050(4) Uiso 1 d . . .
C14 C 0.1789(2) 0.7812(3) -0.48111(11) 0.0496(4) Uani 1 d . . .
H14 H 0.119(3) 0.781(3) -0.5620(17) 0.069(5) Uiso 1 d . . .
C15 C 0.0529(2) 0.7732(2) -0.40163(11) 0.0449(3) Uani 1 d . . .
H15 H -0.104(3) 0.765(3) -0.4250(14) 0.059(5) Uiso 1 d . . .
C16 C 0.14131(18) 0.77692(18) -0.28679(10) 0.0314(3) Uani 1 d . . .
H16 H 0.048(2) 0.774(2) -0.2322(12) 0.035(3) Uiso 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 N5 C6 120.83(9) . . ?
C10 N5 C4 122.01(9) . . ?
C6 N5 C4 117.16(8) . . ?
C7 C6 N5 120.48(10) . . ?
C7 C6 H6 124.9(9) . . ?
N5 C6 H6 114.6(9) . . ?
C10 N1 C2 125.13(9) . . ?
C10 N1 H1 117.7(9) . . ?
C2 N1 H1 116.8(9) . . ?
C6 C7 C8 119.58(10) . . ?
C6 C7 H7 117.5(9) . . ?
C8 C7 H7 122.9(9) . . ?
C9 C8 C7 119.94(10) . . ?
C9 C8 H8 120.6(10) . . ?
C7 C8 H8 119.5(10) . . ?
C8 C9 C10 119.64(10) . . ?
C8 C9 H9 124.2(8) . . ?
C10 C9 H9 116.1(8) . . ?
N1 C10 N5 118.56(9) . . ?
N1 C10 C9 121.97(9) . . ?
N5 C10 C9 119.47(10) . . ?
O2 C2 N1 116.22(9) . . ?
O2 C2 C3 126.31(9) . . ?
N1 C2 C3 117.46(9) . . ?
C4 C3 C2 120.45(9) . . ?
C4 C3 C11 119.13(9) . . ?
C2 C3 C11 120.42(9) . . ?
O4 C4 C3 129.37(10) . . ?
O4 C4 N5 114.63(9) . . ?
C3 C4 N5 116.00(9) . . ?
C12 C11 C16 117.22(9) . . ?
C12 C11 C3 120.76(9) . . ?
C16 C11 C3 122.01(9) . . ?
C13 C12 C11 121.35(10) . . ?
C13 C12 H12 118.5(8) . . ?
C11 C12 H12 120.2(8) . . ?
C12 C13 C14 120.66(11) . . ?
C12 C13 H13 118.2(9) . . ?
C14 C13 H13 121.2(9) . . ?
C15 C14 C13 118.88(11) . . ?
C15 C14 H14 121.9(11) . . ?
C13 C14 H14 119.2(11) . . ?
C14 C15 C16 121.01(11) . . ?
C14 C15 H15 120.9(10) . . ?
C16 C15 H15 118.1(10) . . ?
C15 C16 C11 120.87(11) . . ?
C15 C16 H16 119.0(8) . . ?
C11 C16 H16 120.1(8) . . ?
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
N5 C10 1.3575(13) . ?
N5 C6 1.3770(13) . ?
N5 C4 1.4903(13) . ?
O2 C2 1.2464(12) . ?
C6 C7 1.3558(16) . ?
C6 H6 0.929(15) . ?
N1 C10 1.3376(13) . ?
N1 C2 1.3961(13) . ?
N1 H1 0.929(17) . ?
O4 C4 1.2225(13) . ?
C7 C8 1.4107(17) . ?
C7 H7 0.939(16) . ?
C8 C9 1.3588(16) . ?
C8 H8 0.994(17) . ?
C9 C10 1.4108(15) . ?
C9 H9 0.951(14) . ?
C2 C3 1.4273(14) . ?
C3 C4 1.4115(14) . ?
C3 C11 1.4887(14) . ?
C11 C12 1.4012(15) . ?
C11 C16 1.4028(14) . ?
C12 C13 1.3839(16) . ?
C12 H12 0.989(15) . ?
C13 C14 1.3857(19) . ?
C13 H13 0.983(16) . ?
C14 C15 1.3784(19) . ?
C14 H14 0.979(19) . ?
C15 C16 1.3897(16) . ?
C15 H15 0.999(18) . ?
C16 H16 0.977(14) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N5 C6 C7 -1.55(17) . . . . ?
C4 N5 C6 C7 177.69(10) . . . . ?
N5 C6 C7 C8 -0.72(18) . . . . ?
C6 C7 C8 C9 1.57(19) . . . . ?
C7 C8 C9 C10 -0.19(18) . . . . ?
C2 N1 C10 N5 1.11(16) . . . . ?
C2 N1 C10 C9 -178.73(10) . . . . ?
C6 N5 C10 N1 -176.92(9) . . . . ?
C4 N5 C10 N1 3.87(15) . . . . ?
C6 N5 C10 C9 2.93(16) . . . . ?
C4 N5 C10 C9 -176.28(9) . . . . ?
C8 C9 C10 N1 177.80(10) . . . . ?
C8 C9 C10 N5 -2.04(17) . . . . ?
C10 N1 C2 O2 173.44(9) . . . . ?
C10 N1 C2 C3 -6.14(16) . . . . ?
O2 C2 C3 C4 -173.40(10) . . . . ?
N1 C2 C3 C4 6.14(15) . . . . ?
O2 C2 C3 C11 7.55(16) . . . . ?
N1 C2 C3 C11 -172.91(9) . . . . ?
C2 C3 C4 O4 178.53(11) . . . . ?
C11 C3 C4 O4 -2.41(18) . . . . ?
C2 C3 C4 N5 -1.67(15) . . . . ?
C11 C3 C4 N5 177.39(8) . . . . ?
C10 N5 C4 O4 176.32(10) . . . . ?
C6 N5 C4 O4 -2.91(15) . . . . ?
C10 N5 C4 C3 -3.50(15) . . . . ?
C6 N5 C4 C3 177.27(9) . . . . ?
C4 C3 C11 C12 -153.38(11) . . . . ?
C2 C3 C11 C12 25.68(15) . . . . ?
C4 C3 C11 C16 25.51(16) . . . . ?
C2 C3 C11 C16 -155.43(11) . . . . ?
C16 C11 C12 C13 0.02(18) . . . . ?
C3 C11 C12 C13 178.97(12) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C11 0.3(2) . . . . ?
C12 C11 C16 C15 -0.20(18) . . . . ?
C3 C11 C16 C15 -179.13(12) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 362931
