#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/89/1508901.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_1508901
loop_
_publ_author_name
'Tran, Tuan P.'
'Mullins, Patrick B.'
'Am Ende, Christopher W.'
'Pettersson, Martin'
_publ_section_title
;
 Synthesis of Pyridopyrazine-1,6-diones from 6-Hydroxypicolinic Acids via
 a One-Pot Coupling/Cyclization Reaction.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              642
_journal_page_last               645
_journal_paper_doi               10.1021/ol303463e
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28
_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                 107.622(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2153(16)
_cell_length_b                   7.6831(8)
_cell_length_c                   12.8817(18)
_cell_measurement_reflns_used    1920
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      64.27
_cell_measurement_theta_min      3.51
_cell_volume                     1246.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.585
_diffrn_measured_fraction_theta_max 0.585
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2700
_diffrn_reflns_theta_full        64.69
_diffrn_reflns_theta_max         64.69
_diffrn_reflns_theta_min         3.51
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  0.8081
_exptl_absorpt_correction_T_min  0.6645
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.100
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0398
_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
'calc w=1/[σ²(Fo²)+(0.0614P)²+0.2315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                1136
_reflns_number_total             1228
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303463e_si_002.cif
_cod_data_source_block           z049
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1508901
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.58564(15) 0.6184(2) 0.1956(3) 0.0376(8) Uani 1 1 d .
C2 C 0.56622(16) 0.7776(2) 0.1340(2) 0.0460(8) Uani 1 1 d .
H2 H 0.5367 0.8719 0.1597 0.055 Uiso 1 1 calc R
C3 C 0.58977(16) 0.7928(2) 0.0400(2) 0.0476(8) Uani 1 1 d .
H3 H 0.5759 0.8972 0.0018 0.057 Uiso 1 1 calc R
C4 C 0.63496(14) 0.6542(2) -0.00169(17) 0.0407(7) Uani 1 1 d .
H4 H 0.6507 0.6661 -0.0670 0.049 Uiso 1 1 calc R
C5 C 0.65528(13) 0.5027(2) 0.0550(2) 0.0300(7) Uani 1 1 d .
C6 C 0.64715(15) 0.3161(2) 0.20592(18) 0.0455(7) Uani 1 1 d .
H6A H 0.5870 0.2409 0.1733 0.055 Uiso 1 1 calc R
H6B H 0.6523 0.3322 0.2821 0.055 Uiso 1 1 calc R
C7 C 0.74669(15) 0.2327(2) 0.1971(2) 0.0452(7) Uani 1 1 d .
H7A H 0.8076 0.2988 0.2399 0.054 Uiso 1 1 calc R
H7B H 0.7524 0.1159 0.2270 0.054 Uiso 1 1 calc R
C8 C 0.71081(14) 0.3583(2) 0.0160(2) 0.0372(8) Uani 1 1 d .
C9 C 0.81736(15) 0.0943(2) 0.05759(19) 0.0488(7) Uani 1 1 d .
H9A H 0.7950 0.0775 -0.0207 0.059 Uiso 1 1 calc R
H9B H 0.8096 -0.0159 0.0911 0.059 Uiso 1 1 calc R
C10 C 0.93264(15) 0.1472(2) 0.09472(19) 0.0436(7) Uani 1 1 d .
C11 C 0.99751(17) 0.1066(2) 0.19789(19) 0.0582(8) Uani 1 1 d .
H11 H 0.9705 0.0426 0.2448 0.070 Uiso 1 1 calc R
C12 C 1.10247(19) 0.1606(3) 0.2319(2) 0.0702(9) Uani 1 1 d .
H12 H 1.1452 0.1335 0.3018 0.084 Uiso 1 1 calc R
C13 C 1.14369(19) 0.2535(3) 0.1636(3) 0.0743(10) Uani 1 1 d .
H13 H 1.2143 0.2890 0.1865 0.089 Uiso 1 1 calc R
C14 C 1.08041(19) 0.2934(3) 0.0616(2) 0.0731(9) Uani 1 1 d .
H14 H 1.1081 0.3567 0.0149 0.088 Uiso 1 1 calc R
C15 C 0.97558(17) 0.2409(3) 0.0268(2) 0.0584(8) Uani 1 1 d .
H15 H 0.9334 0.2691 -0.0431 0.070 Uiso 1 1 calc R
N1 N 0.63082(11) 0.48555(16) 0.15025(16) 0.0310(6) Uani 1 1 d .
N2 N 0.74808(11) 0.22410(16) 0.08534(17) 0.0370(6) Uani 1 1 d .
O1 O 0.56571(13) 0.59587(18) 0.28210(18) 0.0555(6) Uani 1 1 d .
O2 O 0.72376(12) 0.36816(17) -0.07418(18) 0.0550(6) Uani 1 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
O1 C1 N1 120.8(2)
O1 C1 C2 124.6(2)
N1 C1 C2 114.7(3)
C3 C2 C1 121.4(2)
C2 C3 C4 121.31(18)
C5 C4 C3 118.8(2)
C4 C5 N1 120.24(19)
C4 C5 C8 119.4(2)
N1 C5 C8 120.23(17)
N1 C6 C7 110.16(18)
N2 C7 C6 111.75(16)
O2 C8 N2 123.0(2)
O2 C8 C5 119.69(18)
N2 C8 C5 117.3(3)
N2 C9 C10 112.60(13)
C15 C10 C11 118.2(2)
C15 C10 C9 120.60(19)
C11 C10 C9 121.2(2)
C10 C11 C12 120.5(2)
C13 C12 C11 120.5(2)
C14 C13 C12 119.4(2)
C13 C14 C15 120.7(3)
C14 C15 C10 120.7(2)
C5 N1 C1 123.55(17)
C5 N1 C6 118.91(16)
C1 N1 C6 117.5(2)
C8 N2 C7 120.65(18)
C8 N2 C9 119.0(2)
C7 N2 C9 118.01(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.232(3)
C1 N1 1.397(3)
C1 C2 1.438(3)
C2 C3 1.343(3)
C3 C4 1.405(3)
C4 C5 1.358(2)
C5 N1 1.366(3)
C5 C8 1.498(3)
C6 N1 1.470(2)
C6 C7 1.498(3)
C7 N2 1.447(3)
C8 O2 1.226(3)
C8 N2 1.356(3)
C9 N2 1.469(2)
C9 C10 1.508(3)
C10 C15 1.381(3)
C10 C11 1.381(3)
C11 C12 1.386(3)
C12 C13 1.368(4)
C13 C14 1.361(4)
C14 C15 1.381(3)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 30652104 ChemSpider
