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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/1/52/04/1520463.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_1520463
loop_
_publ_author_name
'Onyeabo, Romanus O.'
'Edwards, Mark'
'Spencer, John'
'Tizzard, Graham J.'
'Coles, Simon J.'
_publ_section_title
;
 Methoxy oxindole
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              1327
_journal_year                    2010
_chemical_formula_moiety         'C16 H13 N O2'
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.27
_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
_cell_angle_alpha                62.708(3)
_cell_angle_beta                 86.495(4)
_cell_angle_gamma                86.546(4)
_cell_formula_units_Z            2
_cell_length_a                   4.1302(2)
_cell_length_b                   12.9513(9)
_cell_length_c                   13.0829(9)
_cell_measurement_reflns_used    13752
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     620.35(7)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0706
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10272
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.01
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_correction_T_min  0.9859
_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    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.1415
_refine_ls_R_factor_gt           0.0877
_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)+(0.0000P)²+1.1296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1633
_reflns_number_gt                1847
_reflns_number_total             2830
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-1327.cif
_cod_data_source_block           2010src0796a
_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/1327)

More at:
http://ecrystals.chem.soton.ac.uk/1327/
;
_cod_database_code               1520463
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 -0.2601(8) 0.4371(3) 0.3998(3) 0.0351(8) Uani 1 1 d . . .
C2 C -0.0776(7) 0.3595(3) 0.3567(3) 0.0287(7) Uani 1 1 d . . .
C3 C 0.0744(7) 0.2665(3) 0.4578(3) 0.0284(7) Uani 1 1 d . . .
C4 C 0.2812(7) 0.1712(3) 0.4773(3) 0.0319(7) Uani 1 1 d . . .
H4 H 0.3467 0.1541 0.4157 0.038 Uiso 1 1 calc R . .
C5 C 0.3916(8) 0.1012(3) 0.5867(3) 0.0341(8) Uani 1 1 d . . .
H5 H 0.5314 0.0356 0.6000 0.041 Uiso 1 1 calc R . .
C6 C 0.3000(8) 0.1259(3) 0.6770(3) 0.0337(8) Uani 1 1 d . . .
H6 H 0.3761 0.0764 0.7517 0.040 Uiso 1 1 calc R . .
C7 C 0.0984(8) 0.2218(3) 0.6601(3) 0.0350(8) Uani 1 1 d . . .
H7 H 0.0395 0.2399 0.7216 0.042 Uiso 1 1 calc R . .
C8 C -0.0126(7) 0.2896(3) 0.5516(3) 0.0312(7) Uani 1 1 d . . .
C9 C -0.0705(8) 0.3881(3) 0.2445(3) 0.0312(7) Uani 1 1 d . . .
H9 H -0.1669 0.4617 0.1955 0.037 Uiso 1 1 calc R . .
C10 C 0.0692(7) 0.3191(3) 0.1878(3) 0.0303(7) Uani 1 1 d . . .
C11 C 0.0231(8) 0.1996(3) 0.2343(3) 0.0310(7) Uani 1 1 d . . .
H11 H -0.0976 0.1611 0.3050 0.037 Uiso 1 1 calc R . .
C12 C 0.1502(8) 0.1371(3) 0.1790(3) 0.0321(7) Uani 1 1 d . . .
H12 H 0.1158 0.0562 0.2114 0.039 Uiso 1 1 calc R . .
C13 C 0.3274(8) 0.1918(3) 0.0767(3) 0.0329(8) Uani 1 1 d . . .
C14 C 0.3686(8) 0.3097(3) 0.0270(3) 0.0329(8) Uani 1 1 d . . .
H14 H 0.4853 0.3478 -0.0446 0.039 Uiso 1 1 calc R . .
C15 C 0.2367(8) 0.3722(3) 0.0831(3) 0.0320(7) Uani 1 1 d . . .
H15 H 0.2626 0.4538 0.0483 0.038 Uiso 1 1 calc R . .
C16 C 0.6325(9) 0.1717(4) -0.0760(3) 0.0489(10) Uani 1 1 d . . .
H16A H 0.5014 0.2336 -0.1348 0.073 Uiso 1 1 calc R . .
H16B H 0.6962 0.1124 -0.1009 0.073 Uiso 1 1 calc R . .
H16C H 0.8273 0.2045 -0.0650 0.073 Uiso 1 1 calc R . .
N1 N -0.2123(6) 0.3895(2) 0.5148(2) 0.0327(6) Uani 1 1 d . . .
H1 H -0.2971 0.4183 0.5601 0.039 Uiso 1 1 calc R . .
O1 O -0.4289(6) 0.5251(2) 0.3436(2) 0.0422(6) Uani 1 1 d . . .
O2 O 0.4465(6) 0.1201(2) 0.0300(2) 0.0429(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 0.0033 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 125.9(3) . .
O1 C1 C2 127.3(3) . .
N1 C1 C2 106.7(3) . .
C9 C2 C3 134.7(3) . .
C9 C2 C1 119.9(3) . .
C3 C2 C1 105.4(3) . .
C4 C3 C8 118.1(3) . .
C4 C3 C2 135.1(3) . .
C8 C3 C2 106.8(3) . .
C5 C4 C3 119.9(3) . .
C5 C4 H4 120.1 . .
C3 C4 H4 120.1 . .
C6 C5 C4 120.6(3) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C5 C6 C7 121.0(3) . .
C5 C6 H6 119.5 . .
C7 C6 H6 119.5 . .
C8 C7 C6 117.7(3) . .
C8 C7 H7 121.1 . .
C6 C7 H7 121.1 . .
C7 C8 N1 127.7(3) . .
C7 C8 C3 122.6(3) . .
N1 C8 C3 109.7(3) . .
C2 C9 C10 127.7(3) . .
C2 C9 H9 116.1 . .
C10 C9 H9 116.1 . .
C15 C10 C11 117.7(3) . .
C15 C10 C9 120.5(3) . .
C11 C10 C9 121.7(3) . .
C12 C11 C10 120.9(3) . .
C12 C11 H11 119.6 . .
C10 C11 H11 119.6 . .
C11 C12 C13 120.1(3) . .
C11 C12 H12 119.9 . .
C13 C12 H12 119.9 . .
C14 C13 C12 120.4(3) . .
C14 C13 O2 124.6(3) . .
C12 C13 O2 115.0(3) . .
C13 C14 C15 119.0(3) . .
C13 C14 H14 120.5 . .
C15 C14 H14 120.5 . .
C10 C15 C14 121.9(3) . .
C10 C15 H15 119.1 . .
C14 C15 H15 119.1 . .
O2 C16 H16A 109.5 . .
O2 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
O2 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C1 N1 C8 111.5(3) . .
C1 N1 H1 124.3 . .
C8 N1 H1 124.3 . .
C13 O2 C16 117.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.235(4) .
C1 N1 1.361(4) .
C1 C2 1.508(4) .
C2 C9 1.338(4) .
C2 C3 1.465(4) .
C3 C4 1.389(4) .
C3 C8 1.412(4) .
C4 C5 1.386(5) .
C4 H4 0.9500 .
C5 C6 1.385(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 1.391(4) .
C9 C10 1.475(4) .
C9 H9 0.9500 .
C10 C15 1.381(4) .
C10 C11 1.399(4) .
C11 C12 1.376(4) .
C11 H11 0.9500 .
C12 C13 1.379(5) .
C12 H12 0.9500 .
C13 C14 1.375(5) .
C13 O2 1.381(4) .
C14 C15 1.391(4) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 O2 1.429(4) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
N1 H1 0.8800 .
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 2.00 2.864(3) 168.9 2_466
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 727515
