#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/73/2237396.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_2237396
loop_
_publ_author_name
'Topno, Nishith Saurav'
'Tangeti, Venkataswamy'
'Rao, H. Surya Prakash'
'Krishna, R.'
_publ_section_title
;
 (Z)-3-(1-Hydroxy-3-oxobut-1-enyl)-6-nitro-2H-chromen-2-one
;
_journal_coeditor_code           SJ5289
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o284
_journal_paper_doi               10.1107/S1600536812051872
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C13 H9 N O6'
_chemical_formula_moiety         'C13 H9 N O6'
_chemical_formula_sum            'C13 H9 N O6'
_chemical_formula_weight         275.21
_chemical_name_systematic
;
(Z)-3-(1-Hydroxy-3-oxobut-1-enyl)-6-nitro-2H-chromen-2-one
;
_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                85.202(17)
_cell_angle_beta                 77.346(15)
_cell_angle_gamma                89.278(17)
_cell_formula_units_Z            2
_cell_length_a                   7.4591(13)
_cell_length_b                   8.2178(19)
_cell_length_c                   10.0087(18)
_cell_measurement_reflns_used    2257
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1142
_cell_measurement_theta_min      3.1006
_cell_volume                     596.5(2)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4789
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.11
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.199
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0479
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1696
_reflns_number_gt                1395
_reflns_number_total             2093
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5289.cif
_cod_data_source_block           I
_cod_database_code               2237396
_cod_database_fobs_code          2237396
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.25449(19) 0.17075(18) 0.16604(16) 0.0422(5) Uani d . 1 1
C C4 0.5804(3) 0.1391(2) 0.1024(2) 0.0306(5) Uani d . 1 1
C C2 0.4261(3) 0.3162(2) -0.0432(2) 0.0318(5) Uani d . 1 1
C C5 0.7376(3) 0.0665(2) 0.1335(2) 0.0350(6) Uani d . 1 1
H H5 0.8525 0.0887 0.0766 0.042 Uiso calc R 1 1
C C3 0.5812(3) 0.2510(2) -0.0161(2) 0.0329(5) Uani d . 1 1
H H3 0.6927 0.2791 -0.0757 0.040 Uiso calc R 1 1
C C9 0.4119(3) 0.1020(3) 0.1911(2) 0.0337(5) Uani d . 1 1
O O3 0.6017(2) 0.4703(2) -0.23192(17) 0.0497(5) Uani d . 1 1
H H3A 0.5984 0.5364 -0.2974 0.075 Uiso calc R 1 1
O O4 0.4619(3) 0.6406(2) -0.40237(18) 0.0584(6) Uani d . 1 1
C C11 0.2837(3) 0.4849(3) -0.2152(2) 0.0417(6) Uani d . 1 1
H H11 0.1660 0.4551 -0.1668 0.050 Uiso calc R 1 1
C C6 0.7191(3) -0.0382(3) 0.2494(2) 0.0367(6) Uani d . 1 1
C C8 0.3959(3) -0.0051(3) 0.3076(2) 0.0402(6) Uani d . 1 1
H H8 0.2815 -0.0284 0.3648 0.048 Uiso calc R 1 1
O O2 0.1007(2) 0.3272(2) 0.04475(19) 0.0620(6) Uani d . 1 1
C C10 0.4319(3) 0.4287(2) -0.1671(2) 0.0344(6) Uani d . 1 1
N N1 0.8848(3) -0.1149(2) 0.2826(2) 0.0474(6) Uani d . 1 1
C C7 0.5514(3) -0.0762(3) 0.3373(2) 0.0393(6) Uani d . 1 1
H H7 0.5444 -0.1485 0.4149 0.047 Uiso calc R 1 1
C C1 0.2494(3) 0.2775(3) 0.0523(2) 0.0394(6) Uani d . 1 1
O O6 0.8773(3) -0.1692(3) 0.3998(2) 0.0900(8) Uani d . 1 1
O O5 1.0203(2) -0.1232(2) 0.1907(2) 0.0639(6) Uani d . 1 1
C C13 0.1405(4) 0.6402(4) -0.3939(3) 0.0728(9) Uani d . 1 1
H H13A 0.1784 0.6891 -0.4863 0.109 Uiso calc R 1 1
H H13B 0.0716 0.7180 -0.3369 0.109 Uiso calc R 1 1
H H13C 0.0651 0.5462 -0.3932 0.109 Uiso calc R 1 1
C C12 0.3071(4) 0.5893(3) -0.3397(3) 0.0474(6) Uani d . 1 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_site_symmetry_1
_geom_angle
C9 O1 C1 . 123.35(17)
C9 C4 C5 . 118.4(2)
C9 C4 C3 . 117.68(19)
C5 C4 C3 . 123.93(19)
C3 C2 C1 . 119.73(19)
C3 C2 C10 . 120.49(19)
C1 C2 C10 . 119.77(18)
C6 C5 C4 . 118.5(2)
C6 C5 H5 . 120.8
C4 C5 H5 . 120.8
C2 C3 C4 . 121.97(19)
C2 C3 H3 . 119.0
C4 C3 H3 . 119.0
O1 C9 C8 . 117.09(19)
O1 C9 C4 . 120.68(19)
C8 C9 C4 . 122.2(2)
C10 O3 H3A . 109.5
O4 O4 C12 1 0(10)
C10 C11 C12 . 120.7(2)
C10 C11 H11 . 119.7
C12 C11 H11 . 119.7
C5 C6 C7 . 123.2(2)
C5 C6 N1 . 118.6(2)
C7 C6 N1 . 118.2(2)
C7 C8 C9 . 119.0(2)
C7 C8 H8 . 120.5
C9 C8 H8 . 120.5
O2 O2 C1 1 0(10)
O3 C10 C11 . 121.5(2)
O3 C10 C2 . 112.69(18)
C11 C10 C2 . 125.8(2)
O6 N1 O5 . 123.5(2)
O6 N1 C6 . 118.0(2)
O5 N1 C6 . 118.4(2)
C8 C7 C6 . 118.7(2)
C8 C7 H7 . 120.7
C6 C7 H7 . 120.7
O2 C1 O2 1 0.00(18)
O2 C1 O1 1 115.3(2)
O2 C1 O1 . 115.3(2)
O2 C1 C2 1 128.1(2)
O2 C1 C2 . 128.1(2)
O1 C1 C2 . 116.55(18)
C12 C13 H13A . 109.5
C12 C13 H13B . 109.5
H13A C13 H13B . 109.5
C12 C13 H13C . 109.5
H13A C13 H13C . 109.5
H13B C13 H13C . 109.5
O4 C12 O4 1 0.0(2)
O4 C12 C11 1 121.4(2)
O4 C12 C11 . 121.4(2)
O4 C12 C13 1 119.6(2)
O4 C12 C13 . 119.6(2)
C11 C12 C13 . 119.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C9 . 1.360(3)
O1 C1 . 1.385(3)
C4 C9 . 1.391(3)
C4 C5 . 1.392(3)
C4 C3 . 1.438(3)
C2 C3 . 1.341(3)
C2 C1 . 1.470(3)
C2 C10 . 1.476(3)
C5 C6 . 1.368(3)
C5 H5 . 0.9300
C3 H3 . 0.9300
C9 C8 . 1.385(3)
O3 C10 . 1.325(3)
O3 H3A . 0.8200
O4 O4 1 0.000(5)
O4 C12 . 1.247(3)
C11 C10 . 1.361(3)
C11 C12 . 1.432(3)
C11 H11 . 0.9300
C6 C7 . 1.384(3)
C6 N1 . 1.470(3)
C8 C7 . 1.370(3)
C8 H8 . 0.9300
O2 O2 1 0.0000
O2 C1 . 1.192(3)
N1 O6 . 1.210(3)
N1 O5 . 1.214(2)
C7 H7 . 0.9300
C1 O2 1 1.192(3)
C13 C12 . 1.502(4)
C13 H13A . 0.9600
C13 H13B . 0.9600
C13 H13C . 0.9600
C12 O4 1 1.247(3)
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
O3 H3A O4 1 0.82 1.78 2.510(2) 147.3
C11 H11 O2 1 0.93 2.24 2.870(3) 124.5
C3 H3 O5 2_755 0.93 2.58 3.308(3) 135.7
C7 H7 O4 1_546 0.93 2.39 3.304(3) 165.9
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C9 C4 C5 C6 . . 0.2(3)
C3 C4 C5 C6 . . 180.0(2)
C1 C2 C3 C4 . . 2.1(3)
C10 C2 C3 C4 . . -179.02(19)
C9 C4 C3 C2 . . -1.2(3)
C5 C4 C3 C2 . . 178.94(19)
C1 O1 C9 C8 . . -178.8(2)
C1 O1 C9 C4 . . 1.2(3)
C5 C4 C9 O1 . . 179.40(19)
C3 C4 C9 O1 . . -0.4(3)
C5 C4 C9 C8 . . -0.6(3)
C3 C4 C9 C8 . . 179.6(2)
C4 C5 C6 C7 . . 0.3(4)
C4 C5 C6 N1 . . -179.93(18)
O1 C9 C8 C7 . . -179.48(18)
C4 C9 C8 C7 . . 0.5(4)
C12 C11 C10 O3 . . 1.0(4)
C12 C11 C10 C2 . . -177.7(2)
C3 C2 C10 O3 . . -8.2(3)
C1 C2 C10 O3 . . 170.69(19)
C3 C2 C10 C11 . . 170.6(2)
C1 C2 C10 C11 . . -10.5(3)
C5 C6 N1 O6 . . 160.0(2)
C7 C6 N1 O6 . . -20.2(4)
C5 C6 N1 O5 . . -21.4(3)
C7 C6 N1 O5 . . 158.3(2)
C9 C8 C7 C6 . . 0.0(4)
C5 C6 C7 C8 . . -0.4(4)
N1 C6 C7 C8 . . 179.8(2)
O2 O2 C1 O1 1 . 0.00(3)
O2 O2 C1 C2 1 . 0.00(10)
C9 O1 C1 O2 . 1 179.87(19)
C9 O1 C1 O2 . . 179.87(19)
C9 O1 C1 C2 . . -0.4(3)
C3 C2 C1 O2 . 1 178.4(2)
C10 C2 C1 O2 . 1 -0.5(4)
C3 C2 C1 O2 . . 178.4(2)
C10 C2 C1 O2 . . -0.5(4)
C3 C2 C1 O1 . . -1.2(3)
C10 C2 C1 O1 . . 179.84(19)
O4 O4 C12 C11 1 . 0.00(14)
O4 O4 C12 C13 1 . 0.00(10)
C10 C11 C12 O4 . 1 -4.9(4)
C10 C11 C12 O4 . . -4.9(4)
C10 C11 C12 C13 . . 176.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 129845374
