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#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/04/1520461.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_1520461
loop_
_publ_author_name
'Onyeabo, Romanus O.'
'Edwards, Mark'
'Spencer, John'
'Tizzard, Graham J.'
'Coles, Simon J.'
_publ_section_title
;
 Nitro oxindole
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              1325
_journal_year                    2010
_chemical_formula_moiety         'C15 H10 N2 O3'
_chemical_formula_sum            'C15 H10 N2 O3'
_chemical_formula_weight         266.25
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 104.340(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9484(11)
_cell_length_b                   7.9134(10)
_cell_length_c                   16.013(2)
_cell_measurement_reflns_used    17573
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1221.4(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics
'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 66.065
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5492
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9979
_exptl_absorpt_correction_T_min  0.9837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0623
_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)+(0.0169P)²+2.7321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1497
_reflns_number_gt                1475
_reflns_number_total             2062
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-1325.cif
_cod_data_source_block           2010src0794a
_cod_depositor_comments
;
Citation :
Onyeabo, Romanus O and Edwards, Mark and Spencer, John and 
Tizzard, Graham J and Coles, Simon J (2010) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/1325)

More at:
http://ecrystals.chem.soton.ac.uk/1325/
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1520461
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3935(3) 0.7057(4) 0.0215(2) 0.0265(8) Uani 1 1 d . . .
C2 C 0.3223(3) 0.8745(4) 0.0188(2) 0.0257(8) Uani 1 1 d . . .
C3 C 0.3330(3) 0.9528(4) -0.0628(2) 0.0261(8) Uani 1 1 d . . .
C4 C 0.2857(3) 1.1022(4) -0.1065(2) 0.0282(8) Uani 1 1 d . . .
H4 H 0.2396 1.1846 -0.0805 0.034 Uiso 1 1 calc R . .
C5 C 0.3058(4) 1.1302(4) -0.1876(2) 0.0310(8) Uani 1 1 d . . .
H5 H 0.2736 1.2322 -0.2171 0.037 Uiso 1 1 calc R . .
C6 C 0.3730(3) 1.0101(5) -0.2269(2) 0.0315(9) Uani 1 1 d . . .
H6 H 0.3865 1.0319 -0.2826 0.038 Uiso 1 1 calc R . .
C7 C 0.4205(3) 0.8593(4) -0.1855(2) 0.0287(8) Uani 1 1 d . . .
H7 H 0.4648 0.7763 -0.2122 0.034 Uiso 1 1 calc R . .
C8 C 0.4009(3) 0.8349(4) -0.1044(2) 0.0250(8) Uani 1 1 d . . .
C9 C 0.2579(3) 0.9104(4) 0.0811(2) 0.0270(8) Uani 1 1 d . . .
H9 H 0.2631 0.8241 0.1230 0.032 Uiso 1 1 calc R . .
C10 C 0.1806(3) 1.0618(4) 0.0948(2) 0.0263(8) Uani 1 1 d . . .
C11 C 0.2182(3) 1.2238(4) 0.0746(2) 0.0281(8) Uani 1 1 d . . .
H11 H 0.2960 1.2377 0.0508 0.034 Uiso 1 1 calc R . .
C12 C 0.1442(3) 1.3646(4) 0.0887(2) 0.0273(8) Uani 1 1 d . . .
H12 H 0.1708 1.4747 0.0753 0.033 Uiso 1 1 calc R . .
C13 C 0.0308(3) 1.3409(4) 0.1225(2) 0.0271(8) Uani 1 1 d . . .
C14 C -0.0082(3) 1.1833(4) 0.1454(2) 0.0286(8) Uani 1 1 d . . .
H14 H -0.0854 1.1711 0.1699 0.034 Uiso 1 1 calc R . .
C15 C 0.0677(3) 1.0438(4) 0.1319(2) 0.0294(8) Uani 1 1 d . . .
H15 H 0.0430 0.9348 0.1480 0.035 Uiso 1 1 calc R . .
N1 N 0.4382(3) 0.6926(3) -0.05165(18) 0.0268(7) Uani 1 1 d . . .
H1 H 0.4847 0.6058 -0.0644 0.032 Uiso 1 1 calc R . .
N2 N -0.0483(3) 1.4891(4) 0.13815(19) 0.0329(8) Uani 1 1 d . . .
O1 O 0.4080(2) 0.5980(3) 0.07886(16) 0.0326(6) Uani 1 1 d . . .
O2 O 0.0013(3) 1.6293(3) 0.13161(19) 0.0475(8) Uani 1 1 d . . .
O3 O -0.1589(3) 1.4673(3) 0.1568(2) 0.0504(8) 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 0.0033 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
O1 C1 N1 126.0(3) . .
O1 C1 C2 126.9(3) . .
N1 C1 C2 107.2(3) . .
C9 C2 C3 136.2(3) . .
C9 C2 C1 118.3(3) . .
C3 C2 C1 105.1(3) . .
C4 C3 C8 117.7(3) . .
C4 C3 C2 135.4(3) . .
C8 C3 C2 106.8(3) . .
C5 C4 C3 119.9(3) . .
C5 C4 H4 120.0 . .
C3 C4 H4 120.0 . .
C4 C5 C6 120.7(3) . .
C4 C5 H5 119.6 . .
C6 C5 H5 119.6 . .
C7 C6 C5 120.9(3) . .
C7 C6 H6 119.6 . .
C5 C6 H6 119.6 . .
C8 C7 C6 117.4(3) . .
C8 C7 H7 121.3 . .
C6 C7 H7 121.3 . .
C7 C8 N1 127.2(3) . .
C7 C8 C3 123.4(3) . .
N1 C8 C3 109.4(3) . .
C2 C9 C10 130.4(3) . .
C2 C9 H9 114.8 . .
C10 C9 H9 114.8 . .
C11 C10 C15 118.7(3) . .
C11 C10 C9 122.2(3) . .
C15 C10 C9 119.0(3) . .
C12 C11 C10 121.2(3) . .
C12 C11 H11 119.4 . .
C10 C11 H11 119.4 . .
C13 C12 C11 118.3(3) . .
C13 C12 H12 120.9 . .
C11 C12 H12 120.9 . .
C14 C13 C12 122.5(3) . .
C14 C13 N2 118.5(3) . .
C12 C13 N2 118.9(3) . .
C13 C14 C15 118.6(3) . .
C13 C14 H14 120.7 . .
C15 C14 H14 120.7 . .
C14 C15 C10 120.7(3) . .
C14 C15 H15 119.7 . .
C10 C15 H15 119.7 . .
C1 N1 C8 111.4(3) . .
C1 N1 H1 124.3 . .
C8 N1 H1 124.3 . .
O3 N2 O2 123.6(3) . .
O3 N2 C13 118.8(3) . .
O2 N2 C13 117.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.234(4) .
C1 N1 1.356(4) .
C1 C2 1.508(5) .
C2 C9 1.343(5) .
C2 C3 1.475(5) .
C3 C4 1.395(5) .
C3 C8 1.412(5) .
C4 C5 1.379(5) .
C4 H4 0.9500 .
C5 C6 1.398(5) .
C5 H5 0.9500 .
C6 C7 1.390(5) .
C6 H6 0.9500 .
C7 C8 1.373(5) .
C7 H7 0.9500 .
C8 N1 1.402(4) .
C9 C10 1.470(5) .
C9 H9 0.9500 .
C10 C11 1.396(5) .
C10 C15 1.402(5) .
C11 C12 1.384(5) .
C11 H11 0.9500 .
C12 C13 1.380(5) .
C12 H12 0.9500 .
C13 C14 1.382(5) .
C13 N2 1.469(4) .
C14 C15 1.384(5) .
C14 H14 0.9500 .
C15 H15 0.9500 .
N1 H1 0.8800 .
N2 O3 1.221(4) .
N2 O2 1.229(4) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.88 1.98 2.855(4) 173.3 3_665
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 5713403
