#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/89/1508903.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_1508903
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            'C16 H15 Br N2 O2'
_chemical_formula_weight         347.21
_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                 95.3630(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.8197(5)
_cell_length_b                   12.6493(4)
_cell_length_c                   7.2819(2)
_cell_measurement_reflns_used    7286
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      69.95
_cell_measurement_theta_min      2.81
_cell_volume                     1450.79(8)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_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  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8069
_diffrn_reflns_theta_full        70.16
_diffrn_reflns_theta_max         70.16
_diffrn_reflns_theta_min         2.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.916
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_correction_T_min  0.3672
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.674
_refine_diff_density_min         -1.093
_refine_diff_density_rms         0.242
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.204
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0469
_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)+(0.0775P)²+0.8009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1220
_reflns_number_gt                2576
_reflns_number_total             2618
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303463e_si_004.cif
_cod_data_source_block           z080
_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               1508903
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
Br1 Br -0.153796(17) 0.81099(2) 0.22359(4) 0.02323(17) Uani 1 1 d .
C1 C 0.01285(16) 0.88193(19) 0.3357(3) 0.0182(5) Uani 1 1 d .
C2 C -0.04100(17) 0.7888(2) 0.3205(3) 0.0194(5) Uani 1 1 d .
C3 C -0.0122(2) 0.69034(18) 0.3665(4) 0.0200(6) Uani 1 1 d .
H3 H -0.0484 0.6324 0.3510 0.024 Uiso 1 1 calc R
C4 C 0.0730(2) 0.6766(2) 0.4377(4) 0.0192(6) Uani 1 1 d .
H4 H 0.0936 0.6093 0.4680 0.023 Uiso 1 1 calc R
C5 C 0.12506(16) 0.7623(2) 0.4620(3) 0.0177(5) Uani 1 1 d .
C6 C 0.21567(17) 0.7472(2) 0.5386(3) 0.0190(5) Uani 1 1 d .
C7 C 0.21525(17) 0.9364(2) 0.6026(4) 0.0217(5) Uani 1 1 d .
H7A H 0.2564 0.9935 0.6118 0.026 Uiso 1 1 calc R
H7B H 0.1846 0.9380 0.7118 0.026 Uiso 1 1 calc R
C8 C 0.15412(16) 0.95198(19) 0.4336(3) 0.0202(5) Uani 1 1 d .
H8A H 0.1227 1.0172 0.4446 0.024 Uiso 1 1 calc R
H8B H 0.1851 0.9570 0.3251 0.024 Uiso 1 1 calc R
C9 C 0.34772(19) 0.8287(2) 0.6723(4) 0.0227(6) Uani 1 1 d .
H9A H 0.3648 0.7551 0.6813 0.027 Uiso 1 1 calc R
H9B H 0.3525 0.8582 0.7959 0.027 Uiso 1 1 calc R
C10 C 0.40682(17) 0.8885(2) 0.5546(3) 0.0235(6) Uani 1 1 d .
H10A H 0.4026 0.8580 0.4319 0.028 Uiso 1 1 calc R
H10B H 0.3885 0.9616 0.5432 0.028 Uiso 1 1 calc R
C11 C 0.49791(16) 0.8852(2) 0.6345(3) 0.0210(5) Uani 1 1 d .
C12 C 0.5556(2) 0.8158(2) 0.5658(4) 0.0288(7) Uani 1 1 d .
H12 H 0.5373 0.7689 0.4720 0.035 Uiso 1 1 calc R
C13 C 0.6402(2) 0.8159(2) 0.6363(5) 0.0334(7) Uani 1 1 d .
H13 H 0.6781 0.7693 0.5885 0.040 Uiso 1 1 calc R
C14 C 0.66912(19) 0.8844(2) 0.7767(4) 0.0282(6) Uani 1 1 d .
H14 H 0.7259 0.8840 0.8234 0.034 Uiso 1 1 calc R
C15 C 0.61188(18) 0.9538(2) 0.8468(4) 0.0252(6) Uani 1 1 d .
H15 H 0.6303 1.0001 0.9413 0.030 Uiso 1 1 calc R
C16 C 0.52770(18) 0.9539(2) 0.7764(3) 0.0236(6) Uani 1 1 d .
H16 H 0.4901 1.0007 0.8243 0.028 Uiso 1 1 calc R
N1 N 0.09483(14) 0.86187(16) 0.4143(3) 0.0179(4) Uani 1 1 d .
N2 N 0.25934(15) 0.83539(19) 0.5932(3) 0.0206(5) Uani 1 1 d .
O1 O -0.00904(11) 0.97094(14) 0.2836(2) 0.0229(4) Uani 1 1 d .
O2 O 0.24583(12) 0.65743(16) 0.5482(3) 0.0231(4) 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'
Br Br -0.6763 1.2805 '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 121.3(2)
O1 C1 C2 125.0(2)
N1 C1 C2 113.6(2)
C3 C2 C1 123.0(2)
C3 C2 Br1 121.0(2)
C1 C2 Br1 115.92(19)
C2 C3 C4 119.5(2)
C5 C4 C3 119.7(2)
C4 C5 N1 120.1(2)
C4 C5 C6 119.5(2)
N1 C5 C6 120.4(2)
O2 C6 N2 124.0(3)
O2 C6 C5 119.3(2)
N2 C6 C5 116.7(2)
N2 C7 C8 110.5(2)
N1 C8 C7 109.3(2)
N2 C9 C10 111.3(2)
C11 C10 C9 112.6(2)
C12 C11 C16 118.1(3)
C12 C11 C10 121.0(2)
C16 C11 C10 120.9(2)
C13 C12 C11 120.5(3)
C14 C13 C12 120.9(3)
C13 C14 C15 119.0(3)
C16 C15 C14 120.1(3)
C15 C16 C11 121.4(2)
C5 N1 C1 123.9(2)
C5 N1 C8 118.6(2)
C1 N1 C8 117.3(2)
C6 N2 C7 120.2(2)
C6 N2 C9 120.7(2)
C7 N2 C9 118.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.878(3)
C1 O1 1.227(3)
C1 N1 1.391(3)
C1 C2 1.452(4)
C2 C3 1.357(4)
C3 C4 1.409(4)
C4 C5 1.363(4)
C5 N1 1.380(3)
C5 C6 1.501(4)
C6 O2 1.231(3)
C6 N2 1.352(4)
C7 N2 1.460(3)
C7 C8 1.505(4)
C8 N1 1.475(3)
C9 N2 1.464(4)
C9 C10 1.526(4)
C10 C11 1.503(4)
C11 C12 1.393(4)
C11 C16 1.397(4)
C12 C13 1.388(5)
C13 C14 1.384(4)
C14 C15 1.392(4)
C15 C16 1.382(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652106
