#------------------------------------------------------------------------------
#$Date: 2016-08-13 04:39:23 +0300 (Sat, 13 Aug 2016) $
#$Revision: 185790 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/38/1543886.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_1543886
loop_
_publ_author_name
'Bargavi, Srinivasan'
'Nataraj, Poomathi'
'Perumal, Paramasivam T.'
'Lakshmi, Srinivasakannan'
_publ_section_title
;
 5-(2-Hydroxy-5-methoxybenzoyl)-1-methyl-3-nitropyridin-2(1H)-one
;
_journal_issue                   8
_journal_name_full               IUCrData
_journal_page_first              x161235
_journal_paper_doi               10.1107/S2414314616012359
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C14 H12 N2 O6'
_chemical_formula_moiety         'C14 H12 N2 O6'
_chemical_formula_sum            'C14 H12 N2 O6'
_chemical_formula_weight         304.26
_chemical_name_systematic
5-(2-Hydroxy-5-methoxybenzoyl)-1-methyl-3-nitropyridin-2(1H)-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 100.4660(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5891(4)
_cell_length_b                   7.7739(2)
_cell_length_c                   14.1240(4)
_cell_measurement_reflns_used    2062
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.999
_cell_measurement_theta_min      1.995
_cell_volume                     1359.27(7)
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10209
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.788
_diffrn_reflns_theta_min         1.995
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.396
_refine_ls_extinction_coef       0.0065(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2603
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0409
_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)+(0.0549P)²+0.5029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                2210
_reflns_number_total             2603
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su4066sup1.cif
_cod_data_source_block           I
_cod_database_code               1543886
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.34903(10) 0.35190(18) 0.14070(9) 0.0491(4) Uani d 1 . .
H H1O 0.3954(19) 0.328(3) 0.1083(17) 0.073(7) Uiso d 1 . .
O O2 0.52579(9) 0.72712(18) 0.46370(9) 0.0506(3) Uani d 1 . .
O O3 0.15540(9) 0.52987(17) 0.17871(8) 0.0450(3) Uani d 1 . .
O O4 0.00621(11) 0.1998(2) 0.53725(10) 0.0699(5) Uani d 1 . .
O O5 -0.17278(12) 0.3564(3) 0.44625(13) 0.0941(6) Uani d 1 . .
O O6A -0.1779(5) 0.4205(9) 0.2961(4) 0.097(2) Uani d 0.6 A 1
O O6B -0.1684(7) 0.4936(10) 0.3255(5) 0.077(2) Uani d 0.4 A 2
N N1 0.15383(10) 0.24178(17) 0.47099(9) 0.0345(3) Uani d 1 . .
N N2 -0.12793(12) 0.3882(2) 0.37995(13) 0.0554(4) Uani d 1 . .
C C1 0.36915(12) 0.5983(2) 0.36290(10) 0.0326(3) Uani d 1 . .
H H1 0.3237 0.6360 0.4037 0.039 Uiso calc 1 . .
C C2 0.47843(12) 0.6343(2) 0.38467(11) 0.0373(4) Uani d 1 . .
C C3 0.54549(12) 0.5717(2) 0.32474(12) 0.0442(4) Uani d 1 . .
H H3 0.6192 0.5939 0.3394 0.053 Uiso calc 1 . .
C C4 0.50445(13) 0.4774(2) 0.24408(12) 0.0428(4) Uani d 1 . .
H H4 0.5509 0.4351 0.2054 0.051 Uiso calc 1 . .
C C5 0.39424(12) 0.4444(2) 0.21954(11) 0.0350(4) Uani d 1 . .
C C6 0.32676(11) 0.50583(19) 0.28016(10) 0.0301(3) Uani d 1 . .
C C7 0.20704(11) 0.48412(19) 0.25570(10) 0.0310(3) Uani d 1 . .
C C8 0.15132(11) 0.40964(19) 0.33026(10) 0.0303(3) Uani d 1 . .
C C9 0.03961(12) 0.4296(2) 0.32247(11) 0.0355(4) Uani d 1 . .
H H9 0.0005 0.4898 0.2707 0.043 Uiso calc 1 . .
C C10 -0.01181(12) 0.3610(2) 0.39050(12) 0.0387(4) Uani d 1 . .
C C11 0.04319(13) 0.2634(2) 0.47101(12) 0.0406(4) Uani d 1 . .
C C12 0.20469(11) 0.31358(19) 0.40519(10) 0.0310(3) Uani d 1 . .
H H12 0.2788 0.2975 0.4107 0.037 Uiso calc 1 . .
C C13 0.21453(15) 0.1356(3) 0.54895(13) 0.0497(5) Uani d 1 . .
H H13A 0.2888 0.1289 0.5417 0.075 Uiso calc 1 . .
H H13B 0.1841 0.0220 0.5459 0.075 Uiso calc 1 . .
H H13C 0.2102 0.1866 0.6100 0.075 Uiso calc 1 . .
C C14 0.45551(15) 0.7941(3) 0.52332(12) 0.0505(5) Uani d 1 . .
H H14A 0.4037 0.8696 0.4862 0.076 Uiso calc 1 . .
H H14B 0.4970 0.8567 0.5759 0.076 Uiso calc 1 . .
H H14C 0.4185 0.7010 0.5480 0.076 Uiso calc 1 . .
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
C5 O1 H1O 110.0(16)
C2 O2 C14 116.63(12)
C12 N1 C11 123.28(13)
C12 N1 C13 120.16(13)
C11 N1 C13 116.56(13)
O6B N2 O5 116.3(4)
O5 N2 O6A 123.1(3)
O6B N2 C10 118.4(4)
O5 N2 C10 119.62(17)
O6A N2 C10 116.4(3)
C2 C1 C6 120.33(14)
C2 C1 H1 119.8
C6 C1 H1 119.8
O2 C2 C1 123.73(15)
O2 C2 C3 117.28(14)
C1 C2 C3 118.98(15)
C4 C3 C2 120.92(14)
C4 C3 H3 119.5
C2 C3 H3 119.5
C3 C4 C5 120.85(15)
C3 C4 H4 119.6
C5 C4 H4 119.6
O1 C5 C4 123.47(14)
O1 C5 C6 118.19(13)
C4 C5 C6 118.33(14)
C1 C6 C5 120.55(13)
C1 C6 C7 117.98(13)
C5 C6 C7 121.38(13)
O3 C7 C8 120.28(13)
O3 C7 C6 121.85(13)
C8 C7 C6 117.83(12)
C12 C8 C9 117.83(14)
C12 C8 C7 122.20(13)
C9 C8 C7 119.90(13)
C10 C9 C8 120.08(15)
C10 C9 H9 120.0
C8 C9 H9 120.0
C9 C10 C11 122.90(14)
C9 C10 N2 117.90(15)
C11 C10 N2 119.20(15)
O4 C11 N1 117.87(16)
O4 C11 C10 128.61(16)
N1 C11 C10 113.53(13)
N1 C12 C8 122.26(13)
N1 C12 H12 118.9
C8 C12 H12 118.9
N1 C13 H13A 109.5
N1 C13 H13B 109.5
H13A C13 H13B 109.5
N1 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
O2 C14 H14A 109.5
O2 C14 H14B 109.5
H14A C14 H14B 109.5
O2 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.3602(19)
O1 H1O 0.83(2)
O2 C2 1.3714(19)
O2 C14 1.426(2)
O3 C7 1.2144(18)
O4 C11 1.223(2)
O5 N2 1.204(2)
O6A N2 1.261(6)
O6B N2 1.174(8)
N1 C12 1.3421(19)
N1 C11 1.403(2)
N1 C13 1.474(2)
N2 C10 1.458(2)
C1 C2 1.383(2)
C1 C6 1.393(2)
C1 H1 0.9300
C2 C3 1.388(2)
C3 C4 1.374(2)
C3 H3 0.9300
C4 C5 1.392(2)
C4 H4 0.9300
C5 C6 1.395(2)
C6 C7 1.493(2)
C7 C8 1.485(2)
C8 C12 1.368(2)
C8 C9 1.399(2)
C9 C10 1.361(2)
C9 H9 0.9300
C10 C11 1.436(2)
C12 H12 0.9300
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
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
O1 H1O O4 4_665 0.83(2) 1.87(2) 2.6948(17) 173(2)
C4 H4 O4 4_665 0.93 2.56 3.233(2) 129
C14 H14B O3 4_676 0.96 2.41 3.319(2) 158
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
C14 O2 C2 C1 -2.5(2)
C14 O2 C2 C3 178.54(15)
C6 C1 C2 O2 178.76(14)
C6 C1 C2 C3 -2.2(2)
O2 C2 C3 C4 179.98(15)
C1 C2 C3 C4 0.9(2)
C2 C3 C4 C5 1.0(3)
C3 C4 C5 O1 -179.97(16)
C3 C4 C5 C6 -1.5(2)
C2 C1 C6 C5 1.7(2)
C2 C1 C6 C7 -174.70(14)
O1 C5 C6 C1 178.72(14)
C4 C5 C6 C1 0.2(2)
O1 C5 C6 C7 -5.0(2)
C4 C5 C6 C7 176.48(14)
C1 C6 C7 O3 123.47(16)
C5 C6 C7 O3 -52.9(2)
C1 C6 C7 C8 -54.42(19)
C5 C6 C7 C8 129.20(15)
O3 C7 C8 C12 161.23(15)
C6 C7 C8 C12 -20.9(2)
O3 C7 C8 C9 -15.5(2)
C6 C7 C8 C9 162.38(14)
C12 C8 C9 C10 2.9(2)
C7 C8 C9 C10 179.79(14)
C8 C9 C10 C11 -1.4(2)
C8 C9 C10 N2 178.91(15)
O6B N2 C10 C9 -14.6(5)
O5 N2 C10 C9 -167.08(19)
O6A N2 C10 C9 22.9(4)
O6B N2 C10 C11 165.7(4)
O5 N2 C10 C11 13.2(3)
O6A N2 C10 C11 -156.8(4)
C12 N1 C11 O4 -176.21(16)
C13 N1 C11 O4 3.1(2)
C12 N1 C11 C10 3.6(2)
C13 N1 C11 C10 -177.08(14)
C9 C10 C11 O4 178.07(19)
N2 C10 C11 O4 -2.3(3)
C9 C10 C11 N1 -1.7(2)
N2 C10 C11 N1 177.93(14)
C11 N1 C12 C8 -2.3(2)
C13 N1 C12 C8 178.38(15)
C9 C8 C12 N1 -1.1(2)
C7 C8 C12 N1 -177.92(13)

_cod_database_fobs_code 1543886
