#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/81/2218121.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_2218121
loop_
_publ_author_name
'Nirmala, S.'
'Kamala, E. Theboral Sugi'
'Sudha, L.'
'Raj, A. R. Naresh'
'Huq, C. A. M. A.'
_publ_section_title
;
 1-Allyl-3,3-diphenylindolin-2-one
;
_journal_coeditor_code           GW2038
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o834
_journal_paper_doi               10.1107/S1600536808009446
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C23 H19 N O'
_chemical_formula_moiety         'C23 H19 N O'
_chemical_formula_sum            'C23 H19 N O'
_chemical_formula_weight         325.39
_chemical_name_systematic
;
1-Allyl-3,3-diphenylindolin-2-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8449(3)
_cell_length_b                   12.3879(4)
_cell_length_c                   16.0377(4)
_cell_measurement_reflns_used    4984
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.3
_cell_measurement_theta_min      2.54
_cell_volume                     1757.25(9)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Kappa APEX2'
_diffrn_measurement_method       'ω and φ'
_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  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14793
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.63
_diffrn_reflns_theta_min         2.54
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_correction_T_min  0.9779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0502
_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)+(0.0653P)²+0.2107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1415
_reflns_number_gt                2611
_reflns_number_total             3559
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gw2038.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     'p 2ac 2ab'
_cod_database_code               2218121
_cod_database_fobs_code          2218121
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
C C2 0.7623(2) 0.14099(15) 0.09508(12) 0.0367(4) Uani d . 1
C C3 0.7846(2) 0.02597(14) 0.13122(10) 0.0331(3) Uani d . 1
C C4 0.8751(2) -0.02725(15) 0.06249(11) 0.0349(4) Uani d . 1
C C5 0.9240(3) -0.13195(17) 0.05340(13) 0.0454(5) Uani d . 1
H H5 0.9017 -0.1836 0.0937 0.055 Uiso calc R 1
C C6 1.0075(3) -0.1595(2) -0.01711(14) 0.0523(5) Uani d . 1
H H6 1.0420 -0.2299 -0.0239 0.063 Uiso calc R 1
C C7 1.0390(3) -0.0829(2) -0.07656(14) 0.0570(6) Uani d . 1
H H7 1.0952 -0.1025 -0.1231 0.068 Uiso calc R 1
C C8 0.9897(3) 0.0220(2) -0.06920(13) 0.0517(5) Uani d . 1
H H8 1.0119 0.0733 -0.1097 0.062 Uiso calc R 1
C C9 0.9059(2) 0.04807(16) 0.00085(11) 0.0387(4) Uani d . 1
C C10 0.8516(3) 0.24727(19) -0.02570(15) 0.0543(6) Uani d . 1
H H10A 0.9527 0.2513 -0.0490 0.065 Uiso calc R 1
H H10B 0.8404 0.3073 0.0126 0.065 Uiso calc R 1
C C11 0.7411(3) 0.2612(2) -0.09456(17) 0.0675(7) Uani d . 1
H H11 0.7486 0.3252 -0.1246 0.081 Uiso calc R 1
C C12 0.6406(4) 0.1988(3) -0.1170(2) 0.0792(9) Uani d . 1
H H12A 0.6272 0.1334 -0.0894 0.095 Uiso calc R 1
H H12B 0.5781 0.2170 -0.1614 0.095 Uiso calc R 1
C C13 0.8731(2) 0.03991(15) 0.21273(11) 0.0363(4) Uani d . 1
C C14 0.8029(3) 0.08647(16) 0.28170(13) 0.0439(4) Uani d . 1
H H14 0.7018 0.1067 0.2784 0.053 Uiso calc R 1
C C15 0.8814(3) 0.10282(19) 0.35467(14) 0.0534(6) Uani d . 1
H H15 0.8327 0.1333 0.4004 0.064 Uiso calc R 1
C C16 1.0312(3) 0.0745(2) 0.36051(15) 0.0643(7) Uani d . 1
H H16 1.0845 0.0863 0.4097 0.077 Uiso calc R 1
C C17 1.1015(3) 0.0285(3) 0.29290(17) 0.0782(9) Uani d . 1
H H17 1.2028 0.0090 0.2964 0.094 Uiso calc R 1
C C18 1.0225(3) 0.0110(3) 0.21964(15) 0.0597(6) Uani d . 1
H H18 1.0713 -0.0208 0.1745 0.072 Uiso calc R 1
C C19 0.6328(2) -0.03049(15) 0.14321(11) 0.0347(4) Uani d . 1
C C20 0.5121(2) -0.00927(18) 0.09117(14) 0.0446(5) Uani d . 1
H H20 0.5221 0.0426 0.0496 0.054 Uiso calc R 1
C C21 0.3761(3) -0.0640(2) 0.09980(17) 0.0548(6) Uani d . 1
H H21 0.2957 -0.0484 0.0645 0.066 Uiso calc R 1
C C22 0.3604(3) -0.1413(2) 0.16061(17) 0.0572(6) Uani d . 1
H H22 0.2690 -0.1775 0.1669 0.069 Uiso calc R 1
C C23 0.4792(3) -0.1650(2) 0.21185(15) 0.0596(6) Uani d . 1
H H23 0.4688 -0.2178 0.2526 0.072 Uiso calc R 1
C C24 0.6155(3) -0.11038(18) 0.20325(13) 0.0500(5) Uani d . 1
H H24 0.6961 -0.1275 0.2381 0.060 Uiso calc R 1
N N1 0.8393(2) 0.14731(13) 0.02162(10) 0.0414(4) Uani d . 1
O O1 0.69142(19) 0.21379(12) 0.12636(10) 0.0505(4) Uani d . 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_publ_flag
O1 C2 N1 125.14(18) yes
O1 C2 C3 126.65(17) yes
N1 C2 C3 108.20(15) yes
C4 C3 C19 110.95(15) ?
C4 C3 C13 113.58(15) ?
C19 C3 C13 113.16(14) ?
C4 C3 C2 101.25(14) ?
C19 C3 C2 110.88(15) ?
C13 C3 C2 106.26(14) ?
C5 C4 C9 119.81(17) yes
C5 C4 C3 130.89(17) ?
C9 C4 C3 109.29(16) ?
C4 C5 C6 118.9(2) ?
C4 C5 H5 120.5 ?
C6 C5 H5 120.5 ?
C7 C6 C5 120.1(2) ?
C7 C6 H6 119.9 ?
C5 C6 H6 119.9 ?
C6 C7 C8 121.9(2) ?
C6 C7 H7 119.0 ?
C8 C7 H7 119.0 ?
C7 C8 C9 117.4(2) ?
C7 C8 H8 121.3 ?
C9 C8 H8 121.3 ?
C8 C9 C4 121.79(19) yes
C8 C9 N1 128.49(18) yes
C4 C9 N1 109.72(16) yes
N1 C10 C11 115.9(2) yes
N1 C10 H10A 108.3 ?
C11 C10 H10A 108.3 ?
N1 C10 H10B 108.3 ?
C11 C10 H10B 108.3 ?
H10A C10 H10B 107.4 ?
C12 C11 C10 128.2(3) ?
C12 C11 H11 115.9 ?
C10 C11 H11 115.9 ?
C11 C12 H12A 120.0 ?
C11 C12 H12B 120.0 ?
H12A C12 H12B 120.0 ?
C18 C13 C14 118.21(19) ?
C18 C13 C3 122.03(18) ?
C14 C13 C3 119.73(17) ?
C15 C14 C13 120.7(2) ?
C15 C14 H14 119.6 ?
C13 C14 H14 119.6 ?
C16 C15 C14 120.5(2) ?
C16 C15 H15 119.8 ?
C14 C15 H15 119.8 ?
C17 C16 C15 119.2(2) ?
C17 C16 H16 120.4 ?
C15 C16 H16 120.4 ?
C16 C17 C18 120.5(2) ?
C16 C17 H17 119.8 ?
C18 C17 H17 119.8 ?
C13 C18 C17 120.8(2) ?
C13 C18 H18 119.6 ?
C17 C18 H18 119.6 ?
C20 C19 C24 118.03(18) ?
C20 C19 C3 121.12(16) ?
C24 C19 C3 120.69(18) ?
C19 C20 C21 121.1(2) ?
C19 C20 H20 119.4 ?
C21 C20 H20 119.4 ?
C22 C21 C20 119.9(2) ?
C22 C21 H21 120.0 ?
C20 C21 H21 120.0 ?
C23 C22 C21 119.9(2) ?
C23 C22 H22 120.0 ?
C21 C22 H22 120.0 ?
C22 C23 C24 120.2(2) ?
C22 C23 H23 119.9 ?
C24 C23 H23 119.9 ?
C19 C24 C23 120.7(2) ?
C19 C24 H24 119.6 ?
C23 C24 H24 119.6 ?
C2 N1 C9 111.39(15) yes
C2 N1 C10 122.46(18) yes
C9 N1 C10 126.12(17) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C2 O1 1.207(2) yes
C2 N1 1.363(2) yes
C2 C3 1.551(3) ?
C3 C4 1.513(2) ?
C3 C19 1.526(3) ?
C3 C13 1.533(2) ?
C4 C5 1.375(3) ?
C4 C9 1.387(3) ?
C5 C6 1.393(3) ?
C5 H5 0.9300 ?
C6 C7 1.374(3) ?
C6 H6 0.9300 ?
C7 C8 1.375(4) ?
C7 H7 0.9300 ?
C8 C9 1.384(3) ?
C8 H8 0.9300 ?
C9 N1 1.404(3) yes
C10 N1 1.456(3) yes
C10 C11 1.485(4) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 C12 1.232(4) ?
C11 H11 0.9300 ?
C12 H12A 0.9300 ?
C12 H12B 0.9300 ?
C13 C18 1.374(3) ?
C13 C14 1.393(3) ?
C14 C15 1.376(3) ?
C14 H14 0.9300 ?
C15 C16 1.374(4) ?
C15 H15 0.9300 ?
C16 C17 1.373(4) ?
C16 H16 0.9300 ?
C17 C18 1.384(3) ?
C17 H17 0.9300 ?
C18 H18 0.9300 ?
C19 C20 1.380(3) ?
C19 C24 1.389(3) ?
C20 C21 1.388(3) ?
C20 H20 0.9300 ?
C21 C22 1.374(4) ?
C21 H21 0.9300 ?
C22 C23 1.366(4) ?
C22 H22 0.9300 ?
C23 C24 1.390(3) ?
C23 H23 0.9300 ?
C24 H24 0.9300 ?
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
C12 H12A N1 . 0.93 2.59 2.905(4) 100 yes
C10 H10A O1 4_555 0.97 2.49 3.446(3) 170 yes
C23 H23 O1 3_645 0.93 2.55 3.356(3) 146 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
O1 C2 C3 C4 177.4(2)
N1 C2 C3 C4 -3.70(18)
O1 C2 C3 C19 59.6(2)
N1 C2 C3 C19 -121.48(16)
O1 C2 C3 C13 -63.8(2)
N1 C2 C3 C13 115.17(16)
C19 C3 C4 C5 -57.8(3)
C13 C3 C4 C5 71.0(3)
C2 C3 C4 C5 -175.6(2)
C19 C3 C4 C9 120.96(17)
C13 C3 C4 C9 -110.24(17)
C2 C3 C4 C9 3.23(18)
C9 C4 C5 C6 1.6(3)
C3 C4 C5 C6 -179.68(19)
C4 C5 C6 C7 -0.5(3)
C5 C6 C7 C8 -0.3(4)
C6 C7 C8 C9 -0.2(4)
C7 C8 C9 C4 1.4(3)
C7 C8 C9 N1 -177.8(2)
C5 C4 C9 C8 -2.2(3)
C3 C4 C9 C8 178.88(19)
C5 C4 C9 N1 177.21(18)
C3 C4 C9 N1 -1.7(2)
N1 C10 C11 C12 -0.3(4)
C4 C3 C13 C18 3.0(3)
C19 C3 C13 C18 130.7(2)
C2 C3 C13 C18 -107.4(2)
C4 C3 C13 C14 -179.13(17)
C19 C3 C13 C14 -51.5(2)
C2 C3 C13 C14 70.4(2)
C18 C13 C14 C15 -0.1(3)
C3 C13 C14 C15 -177.99(18)
C13 C14 C15 C16 0.7(4)
C14 C15 C16 C17 -0.7(4)
C15 C16 C17 C18 0.1(5)
C14 C13 C18 C17 -0.6(4)
C3 C13 C18 C17 177.3(3)
C16 C17 C18 C13 0.6(5)
C4 C3 C19 C20 -80.4(2)
C13 C3 C19 C20 150.58(17)
C2 C3 C19 C20 31.3(2)
C4 C3 C19 C24 95.0(2)
C13 C3 C19 C24 -34.0(2)
C2 C3 C19 C24 -153.30(18)
C24 C19 C20 C21 1.6(3)
C3 C19 C20 C21 177.17(19)
C19 C20 C21 C22 -0.5(4)
C20 C21 C22 C23 -0.7(4)
C21 C22 C23 C24 0.6(4)
C20 C19 C24 C23 -1.7(3)
C3 C19 C24 C23 -177.3(2)
C22 C23 C24 C19 0.6(4)
O1 C2 N1 C9 -178.1(2)
C3 C2 N1 C9 3.0(2)
O1 C2 N1 C10 3.8(3)
C3 C2 N1 C10 -175.20(18)
C8 C9 N1 C2 178.5(2)
C4 C9 N1 C2 -0.8(2)
C8 C9 N1 C10 -3.4(4)
C4 C9 N1 C10 177.25(19)
C11 C10 N1 C2 -96.5(3)
C11 C10 N1 C9 85.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9834589
