#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/81/2218120.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_2218120
loop_
_publ_author_name
'Nirmala, S.'
'Theboral Sugi Kamala, E.'
'Sudha, L.'
'Naresh Raj, A. R.'
'Huq, C. A. M. A.'
_publ_section_title
;
 1-Allyl-3,3-di-p-tolylindolin-2-one
;
_journal_coeditor_code           GW2036
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o879
_journal_paper_doi               10.1107/S1600536808010088
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C25 H23 N O'
_chemical_formula_moiety         'C25 H23 N O'
_chemical_formula_sum            'C25 H23 N O'
_chemical_formula_weight         353.44
_chemical_name_systematic
;
1-Allyl-3,3-di-p-tolylindolin-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                92.1630(10)
_cell_angle_beta                 103.1920(10)
_cell_angle_gamma                101.5200(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3311(2)
_cell_length_b                   9.5793(2)
_cell_length_c                   11.5736(2)
_cell_measurement_reflns_used    9112
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      2.30
_cell_volume                     983.15(3)
_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 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_diffrn_measurement_method       'ω and φ scan'
_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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25969
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         31.01
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_correction_T_min  0.9815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         6260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0514
_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)+(0.0731P)²+0.1889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1560
_reflns_number_gt                4310
_reflns_number_total             6260
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gw2036.cif
_cod_data_source_block           I
_cod_database_code               2218120
_cod_database_fobs_code          2218120
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
C C2 0.21981(13) 0.10769(13) 0.14416(10) 0.0403(2) Uani d . 1
C C3 0.29661(11) 0.03653(12) 0.25302(9) 0.0361(2) Uani d . 1
C C4 0.45434(12) 0.05217(12) 0.23447(10) 0.0391(2) Uani d . 1
C C5 0.57669(13) 0.00390(15) 0.29710(12) 0.0497(3) Uani d . 1
H H5 0.5699 -0.0478 0.3628 0.060 Uiso calc R 1
C C6 0.71037(15) 0.03411(17) 0.26019(15) 0.0602(4) Uani d . 1
H H6 0.7938 0.0024 0.3018 0.072 Uiso calc R 1
C C7 0.72086(16) 0.10999(18) 0.16332(16) 0.0629(4) Uani d . 1
H H7 0.8116 0.1295 0.1405 0.075 Uiso calc R 1
C C8 0.59809(17) 0.15830(17) 0.09859(14) 0.0587(4) Uani d . 1
H H8 0.6049 0.2096 0.0327 0.070 Uiso calc R 1
C C9 0.46580(14) 0.12724(13) 0.13582(11) 0.0443(3) Uani d . 1
C C10 0.29599(19) 0.24323(18) -0.01709(12) 0.0614(4) Uani d . 1
H H10A 0.1917 0.2102 -0.0604 0.074 Uiso calc R 1
H H10B 0.3589 0.2267 -0.0701 0.074 Uiso calc R 1
C C11 0.32409(19) 0.39967(19) 0.01642(16) 0.0658(4) Uani d . 1
H H11 0.3133 0.4583 -0.0458 0.079 Uiso calc R 1
C C12 0.3620(2) 0.4623(2) 0.12318(19) 0.0749(5) Uani d . 1
H H12A 0.3742 0.4084 0.1885 0.090 Uiso calc R 1
H H12B 0.3770 0.5612 0.1347 0.090 Uiso calc R 1
C C13 0.22090(12) -0.12027(12) 0.25034(10) 0.0391(2) Uani d . 1
C C14 0.24490(16) -0.19198(15) 0.35239(13) 0.0541(3) Uani d . 1
H H14 0.3029 -0.1423 0.4237 0.065 Uiso calc R 1
C C15 0.18392(18) -0.33608(16) 0.34970(16) 0.0626(4) Uani d . 1
H H15 0.2020 -0.3818 0.4194 0.075 Uiso calc R 1
C C16 0.09700(17) -0.41371(15) 0.24620(16) 0.0592(4) Uani d . 1
C C17 0.07309(17) -0.34194(16) 0.14492(15) 0.0603(4) Uani d . 1
H H17 0.0145 -0.3920 0.0739 0.072 Uiso calc R 1
C C18 0.13362(15) -0.19778(14) 0.14583(12) 0.0490(3) Uani d . 1
H H18 0.1156 -0.1526 0.0759 0.059 Uiso calc R 1
C C19 0.0294(3) -0.57073(17) 0.2435(2) 0.0907(6) Uani d . 1
H H19A -0.0262 -0.6064 0.1639 0.136 Uiso calc R 1
H H19B -0.0372 -0.5842 0.2963 0.136 Uiso calc R 1
H H19C 0.1083 -0.6216 0.2686 0.136 Uiso calc R 1
C C20 0.28928(12) 0.12652(12) 0.36267(10) 0.0372(2) Uani d . 1
C C21 0.40937(13) 0.23204(14) 0.42458(11) 0.0445(3) Uani d . 1
H H21 0.5003 0.2467 0.4020 0.053 Uiso calc R 1
C C22 0.39541(16) 0.31600(15) 0.51984(12) 0.0530(3) Uani d . 1
H H22 0.4778 0.3858 0.5605 0.064 Uiso calc R 1
C C23 0.26275(17) 0.29871(17) 0.55575(12) 0.0553(3) Uani d . 1
C C24 0.14184(16) 0.19372(17) 0.49283(13) 0.0561(3) Uani d . 1
H H24 0.0506 0.1801 0.5150 0.067 Uiso calc R 1
C C25 0.15471(14) 0.10923(15) 0.39803(12) 0.0483(3) Uani d . 1
H H25 0.0721 0.0398 0.3573 0.058 Uiso calc R 1
C C26 0.2485(3) 0.3901(3) 0.65992(18) 0.0932(7) Uani d . 1
H H26A 0.1485 0.3626 0.6718 0.140 Uiso calc R 1
H H26B 0.2675 0.4889 0.6439 0.140 Uiso calc R 1
H H26C 0.3204 0.3771 0.7304 0.140 Uiso calc R 1
N N1 0.32609(13) 0.15965(12) 0.08421(9) 0.0484(3) Uani d . 1
O O1 0.08971(10) 0.11949(10) 0.11825(8) 0.0515(2) 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 0.0016 '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_publ_flag
O1 C2 N1 125.45(11) yes
O1 C2 C3 126.57(11) yes
N1 C2 C3 107.95(9) yes
C4 C3 C13 111.14(9) ?
C4 C3 C20 113.55(9) ?
C13 C3 C20 112.94(9) ?
C4 C3 C2 101.28(9) ?
C13 C3 C2 111.74(9) ?
C20 C3 C2 105.46(9) ?
C5 C4 C9 119.89(11) yes
C5 C4 C3 130.70(11) ?
C9 C4 C3 109.40(9) ?
C4 C5 C6 118.68(13) ?
C4 C5 H5 120.7 ?
C6 C5 H5 120.7 ?
C7 C6 C5 120.88(13) ?
C7 C6 H6 119.6 ?
C5 C6 H6 119.6 ?
C6 C7 C8 121.13(13) ?
C6 C7 H7 119.4 ?
C8 C7 H7 119.4 ?
C9 C8 C7 117.48(14) ?
C9 C8 H8 121.3 ?
C7 C8 H8 121.3 ?
C8 C9 C4 121.93(12) yes
C8 C9 N1 128.51(12) yes
C4 C9 N1 109.54(10) yes
N1 C10 C11 113.55(13) yes
N1 C10 H10A 108.9 ?
C11 C10 H10A 108.9 ?
N1 C10 H10B 108.9 ?
C11 C10 H10B 108.9 ?
H10A C10 H10B 107.7 ?
C12 C11 C10 126.66(15) ?
C12 C11 H11 116.7 ?
C10 C11 H11 116.7 ?
C11 C12 H12A 120.0 ?
C11 C12 H12B 120.0 ?
H12A C12 H12B 120.0 ?
C18 C13 C14 117.85(12) ?
C18 C13 C3 121.72(11) ?
C14 C13 C3 120.33(10) ?
C15 C14 C13 120.95(13) ?
C15 C14 H14 119.5 ?
C13 C14 H14 119.5 ?
C16 C15 C14 121.51(14) ?
C16 C15 H15 119.2 ?
C14 C15 H15 119.2 ?
C15 C16 C17 117.38(13) ?
C15 C16 C19 121.49(17) ?
C17 C16 C19 121.13(17) ?
C16 C17 C18 121.93(14) ?
C16 C17 H17 119.0 ?
C18 C17 H17 119.0 ?
C17 C18 C13 120.39(13) ?
C17 C18 H18 119.8 ?
C13 C18 H18 119.8 ?
C16 C19 H19A 109.5 ?
C16 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C16 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C21 C20 C25 117.95(11) ?
C21 C20 C3 122.56(10) ?
C25 C20 C3 119.36(10) ?
C20 C21 C22 120.67(12) ?
C20 C21 H21 119.7 ?
C22 C21 H21 119.7 ?
C23 C22 C21 121.62(13) ?
C23 C22 H22 119.2 ?
C21 C22 H22 119.2 ?
C22 C23 C24 117.66(13) ?
C22 C23 C26 121.35(15) ?
C24 C23 C26 120.99(15) ?
C25 C24 C23 121.17(13) ?
C25 C24 H24 119.4 ?
C23 C24 H24 119.4 ?
C24 C25 C20 120.91(12) ?
C24 C25 H25 119.5 ?
C20 C25 H25 119.5 ?
C23 C26 H26A 109.5 ?
C23 C26 H26B 109.5 ?
H26A C26 H26B 109.5 ?
C23 C26 H26C 109.5 ?
H26A C26 H26C 109.5 ?
H26B C26 H26C 109.5 ?
C2 N1 C9 111.71(10) yes
C2 N1 C10 122.67(11) yes
C9 N1 C10 125.57(12) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C2 O1 1.2114(14) yes
C2 N1 1.3621(16) yes
C2 C3 1.5535(15) ?
C3 C4 1.5143(15) ?
C3 C13 1.5228(16) ?
C3 C20 1.5294(16) ?
C4 C5 1.3788(16) ?
C4 C9 1.3853(17) ?
C5 C6 1.3895(19) ?
C5 H5 0.9300 ?
C6 C7 1.371(2) ?
C6 H6 0.9300 ?
C7 C8 1.391(2) ?
C7 H7 0.9300 ?
C8 C9 1.3798(19) ?
C8 H8 0.9300 ?
C9 N1 1.4046(16) yes
C10 N1 1.4508(16) yes
C10 C11 1.489(2) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 C12 1.293(3) ?
C11 H11 0.9300 ?
C12 H12A 0.9300 ?
C12 H12B 0.9300 ?
C13 C18 1.3852(17) ?
C13 C14 1.3853(17) ?
C14 C15 1.380(2) ?
C14 H14 0.9300 ?
C15 C16 1.376(2) ?
C15 H15 0.9300 ?
C16 C17 1.378(2) ?
C16 C19 1.507(2) ?
C17 C18 1.382(2) ?
C17 H17 0.9300 ?
C18 H18 0.9300 ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 0.9600 ?
C20 C21 1.3847(16) ?
C20 C25 1.3885(16) ?
C21 C22 1.3857(19) ?
C21 H21 0.9300 ?
C22 C23 1.375(2) ?
C22 H22 0.9300 ?
C23 C24 1.390(2) ?
C23 C26 1.509(2) ?
C24 C25 1.380(2) ?
C24 H24 0.9300 ?
C25 H25 0.9300 ?
C26 H26A 0.9600 ?
C26 H26B 0.9600 ?
C26 H26C 0.9600 ?
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
C5 H5 Cg 2_656 0.93 2.94 3.740(2) 145 yes
C12 H12A N1 . 0.93 2.54 2.858(2) 100 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 178.68(12)
N1 C2 C3 C4 -3.41(12)
O1 C2 C3 C13 60.29(16)
N1 C2 C3 C13 -121.80(11)
O1 C2 C3 C20 -62.78(15)
N1 C2 C3 C20 115.14(10)
C13 C3 C4 C5 -57.30(16)
C20 C3 C4 C5 71.33(16)
C2 C3 C4 C5 -176.12(13)
C13 C3 C4 C9 121.92(11)
C20 C3 C4 C9 -109.45(11)
C2 C3 C4 C9 3.10(12)
C9 C4 C5 C6 1.0(2)
C3 C4 C5 C6 -179.88(12)
C4 C5 C6 C7 -0.2(2)
C5 C6 C7 C8 -0.4(2)
C6 C7 C8 C9 0.2(2)
C7 C8 C9 C4 0.7(2)
C7 C8 C9 N1 -177.86(14)
C5 C4 C9 C8 -1.2(2)
C3 C4 C9 C8 179.45(12)
C5 C4 C9 N1 177.52(12)
C3 C4 C9 N1 -1.79(14)
N1 C10 C11 C12 -4.5(3)
C4 C3 C13 C18 -91.47(13)
C20 C3 C13 C18 139.57(11)
C2 C3 C13 C18 20.86(15)
C4 C3 C13 C14 84.82(14)
C20 C3 C13 C14 -44.14(14)
C2 C3 C13 C14 -162.84(11)
C18 C13 C14 C15 0.1(2)
C3 C13 C14 C15 -176.30(13)
C13 C14 C15 C16 -0.2(2)
C14 C15 C16 C17 0.0(2)
C14 C15 C16 C19 -179.48(16)
C15 C16 C17 C18 0.2(2)
C19 C16 C17 C18 179.68(15)
C16 C17 C18 C13 -0.2(2)
C14 C13 C18 C17 0.1(2)
C3 C13 C18 C17 176.45(12)
C4 C3 C20 C21 11.87(15)
C13 C3 C20 C21 139.58(11)
C2 C3 C20 C21 -98.13(12)
C4 C3 C20 C25 -172.36(10)
C13 C3 C20 C25 -44.66(14)
C2 C3 C20 C25 77.64(13)
C25 C20 C21 C22 0.88(18)
C3 C20 C21 C22 176.71(11)
C20 C21 C22 C23 -0.5(2)
C21 C22 C23 C24 -0.2(2)
C21 C22 C23 C26 179.75(16)
C22 C23 C24 C25 0.4(2)
C26 C23 C24 C25 -179.55(16)
C23 C24 C25 C20 0.1(2)
C21 C20 C25 C24 -0.69(19)
C3 C20 C25 C24 -176.65(12)
O1 C2 N1 C9 -179.43(12)
C3 C2 N1 C9 2.63(14)
O1 C2 N1 C10 3.1(2)
C3 C2 N1 C10 -174.88(12)
C8 C9 N1 C2 178.07(13)
C4 C9 N1 C2 -0.58(15)
C8 C9 N1 C10 -4.5(2)
C4 C9 N1 C10 176.83(13)
C11 C10 N1 C2 88.62(17)
C11 C10 N1 C9 -88.53(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21117957
