#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/55/2235556.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_2235556
loop_
_publ_author_name
'Asiri, Abdullah M.'
'Zayed, Mohie E. M.'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 3-[(E)-Benzylidene]indolin-2-one
;
_journal_coeditor_code           MW2072
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2020
_journal_paper_doi               10.1107/S1600536812024762
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C15 H11 N O'
_chemical_formula_moiety         'C15 H11 N O'
_chemical_formula_sum            'C15 H11 N O'
_chemical_formula_weight         221.25
_chemical_name_systematic
;
3-[(E)-Benzylidene]indolin-2-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.0270(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.9796(3)
_cell_length_b                   22.2266(19)
_cell_length_c                   12.2484(10)
_cell_measurement_reflns_used    3166
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.5
_cell_volume                     1079.24(15)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ω
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6831
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2460
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0633P)²+0.2809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                2153
_reflns_number_total             2460
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            mw2072.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2235556
_cod_database_fobs_code          2235556
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.5372(2) 0.58258(4) 0.53379(7) 0.0236(2) Uani d . 1 1
N N1 0.7366(3) 0.52725(4) 0.39388(8) 0.0183(2) Uani d D 1 1
H H1N 0.668(4) 0.4920(5) 0.4133(12) 0.032(4) Uiso d D 1 1
C C1 0.8893(3) 0.53924(5) 0.29780(9) 0.0167(2) Uani d . 1 1
C C2 0.9905(3) 0.49792(5) 0.22291(10) 0.0194(3) Uani d . 1 1
H H2 0.9556 0.4560 0.2321 0.023 Uiso calc R 1 1
C C3 1.1456(3) 0.52014(6) 0.13341(10) 0.0211(3) Uani d . 1 1
H H3 1.2194 0.4929 0.0808 0.025 Uiso calc R 1 1
C C4 1.1938(3) 0.58149(6) 0.11990(10) 0.0207(3) Uani d . 1 1
H H4 1.2987 0.5956 0.0580 0.025 Uiso calc R 1 1
C C5 1.0897(3) 0.62256(5) 0.19619(9) 0.0184(2) Uani d . 1 1
H H5 1.1241 0.6645 0.1866 0.022 Uiso calc R 1 1
C C6 0.9350(3) 0.60162(5) 0.28646(9) 0.0159(2) Uani d . 1 1
C C7 0.8052(3) 0.62991(5) 0.38267(9) 0.0167(2) Uani d . 1 1
C C8 0.6761(3) 0.57888(5) 0.44818(9) 0.0180(3) Uani d . 1 1
C C9 0.7925(3) 0.68631(5) 0.42166(9) 0.0176(2) Uani d . 1 1
H H9 0.7175 0.6901 0.4929 0.021 Uiso calc R 1 1
C C10 0.8793(3) 0.74284(5) 0.36866(9) 0.0167(2) Uani d . 1 1
C C11 0.7759(3) 0.75418(5) 0.25856(9) 0.0179(2) Uani d . 1 1
H H11 0.6540 0.7243 0.2161 0.021 Uiso calc R 1 1
C C12 0.8496(3) 0.80862(5) 0.21070(10) 0.0194(3) Uani d . 1 1
H H12 0.7756 0.8160 0.1360 0.023 Uiso calc R 1 1
C C13 1.0311(3) 0.85235(5) 0.27155(10) 0.0199(3) Uani d . 1 1
H H13 1.0862 0.8892 0.2382 0.024 Uiso calc R 1 1
C C14 1.1317(3) 0.84202(5) 0.38124(10) 0.0203(3) Uani d . 1 1
H H14 1.2557 0.8719 0.4231 0.024 Uiso calc R 1 1
C C15 1.0516(3) 0.78813(5) 0.43000(9) 0.0191(3) Uani d . 1 1
H H15 1.1145 0.7819 0.5058 0.023 Uiso calc R 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
C8 N1 C1 111.10(9)
C8 N1 H1N 123.7(11)
C1 N1 H1N 124.9(11)
C2 C1 N1 127.28(11)
C2 C1 C6 122.79(11)
N1 C1 C6 109.93(10)
C1 C2 C3 117.44(11)
C1 C2 H2 121.3
C3 C2 H2 121.3
C4 C3 C2 121.10(11)
C4 C3 H3 119.4
C2 C3 H3 119.4
C3 C4 C5 120.69(11)
C3 C4 H4 119.7
C5 C4 H4 119.7
C4 C5 C6 119.42(11)
C4 C5 H5 120.3
C6 C5 H5 120.3
C5 C6 C1 118.55(10)
C5 C6 C7 134.85(11)
C1 C6 C7 106.56(10)
C9 C7 C6 135.33(11)
C9 C7 C8 119.22(10)
C6 C7 C8 105.40(9)
O1 C8 N1 125.86(10)
O1 C8 C7 127.13(10)
N1 C8 C7 106.99(10)
C7 C9 C10 128.54(10)
C7 C9 H9 115.7
C10 C9 H9 115.7
C11 C10 C15 118.50(10)
C11 C10 C9 121.32(10)
C15 C10 C9 120.08(10)
C12 C11 C10 120.65(11)
C12 C11 H11 119.7
C10 C11 H11 119.7
C13 C12 C11 120.20(11)
C13 C12 H12 119.9
C11 C12 H12 119.9
C14 C13 C12 119.78(11)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C14 C15 120.12(11)
C13 C14 H14 119.9
C15 C14 H14 119.9
C14 C15 C10 120.67(11)
C14 C15 H15 119.7
C10 C15 H15 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.2302(14)
N1 C8 1.3585(15)
N1 C1 1.3968(14)
N1 H1N 0.870(10)
C1 C2 1.3825(16)
C1 C6 1.4068(16)
C2 C3 1.3946(17)
C2 H2 0.9500
C3 C4 1.3890(18)
C3 H3 0.9500
C4 C5 1.3950(16)
C4 H4 0.9500
C5 C6 1.3919(15)
C5 H5 0.9500
C6 C7 1.4689(15)
C7 C9 1.3439(16)
C7 C8 1.5054(15)
C9 C10 1.4693(15)
C9 H9 0.9500
C10 C11 1.3978(16)
C10 C15 1.3993(16)
C11 C12 1.3871(16)
C11 H11 0.9500
C12 C13 1.3884(17)
C12 H12 0.9500
C13 C14 1.3871(17)
C13 H13 0.9500
C14 C15 1.3881(16)
C14 H14 0.9500
C15 H15 0.9500
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
_geom_hbond_publ_flag
N1 H1N O1 3_666 0.870(10) 1.983(9) 2.8460(10) 172.3(15) yes
C13 H13 O1 4_675 0.95 2.57 3.2535(15) 129 yes
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
C8 N1 C1 C2 179.20(11)
C8 N1 C1 C6 0.09(13)
N1 C1 C2 C3 -178.59(11)
C6 C1 C2 C3 0.41(16)
C1 C2 C3 C4 -0.48(17)
C2 C3 C4 C5 0.40(17)
C3 C4 C5 C6 -0.23(17)
C4 C5 C6 C1 0.15(16)
C4 C5 C6 C7 177.75(11)
C2 C1 C6 C5 -0.25(16)
N1 C1 C6 C5 178.91(10)
C2 C1 C6 C7 -178.47(10)
N1 C1 C6 C7 0.68(12)
C5 C6 C7 C9 -1.8(2)
C1 C6 C7 C9 175.99(13)
C5 C6 C7 C8 -178.91(12)
C1 C6 C7 C8 -1.11(11)
C1 N1 C8 O1 178.19(11)
C1 N1 C8 C7 -0.80(13)
C9 C7 C8 O1 4.54(18)
C6 C7 C8 O1 -177.79(11)
C9 C7 C8 N1 -176.49(10)
C6 C7 C8 N1 1.18(12)
C6 C7 C9 C10 8.2(2)
C8 C7 C9 C10 -175.00(11)
C7 C9 C10 C11 43.93(18)
C7 C9 C10 C15 -139.89(13)
C15 C10 C11 C12 1.47(17)
C9 C10 C11 C12 177.71(10)
C10 C11 C12 C13 0.77(17)
C11 C12 C13 C14 -1.57(17)
C12 C13 C14 C15 0.09(18)
C13 C14 C15 C10 2.20(18)
C11 C10 C15 C14 -2.95(17)
C9 C10 C15 C14 -179.24(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 663730
