#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/13/2231384.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_2231384
loop_
_publ_author_name
'Yuan, Maosen'
'Wang, Qi'
'Zhang, Shujun'
'Gao, Peng'
'Wang, Junru'
_publ_section_title
;
 3-(Diphenylmethylidene)indolin-2-one
;
_journal_coeditor_code           ZS2123
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2098
_journal_paper_doi               10.1107/S1600536811028467
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H15 N O'
_chemical_formula_moiety         'C21 H15 N O'
_chemical_formula_sum            'C21 H15 N O'
_chemical_formula_weight         297.34
_chemical_name_systematic
;
3-(Diphenylmethylidene)indolin-2-one
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 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                   11.0679(11)
_cell_length_b                   17.6465(16)
_cell_length_c                   7.8835(6)
_cell_measurement_reflns_used    1702
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.023
_cell_measurement_theta_min      2.83
_cell_volume                     1539.7(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0496
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9094
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.47
_diffrn_reflns_theta_min         2.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9707
_exptl_absorpt_correction_T_min  0.9647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.151
_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     208
_refine_ls_number_reflns         2072
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0374
_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)+(0.0323P)²+0.1729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                1105
_reflns_number_total             2072
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2123.cif
_cod_data_source_block           I
_cod_database_code               2231384
_cod_database_fobs_code          2231384
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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
N N1 0.4749(2) 0.42487(13) 0.0945(4) 0.0564(7) Uani d . 1 1
H H1 0.4439 0.4611 0.0361 0.068 Uiso calc R 1 1
O O1 0.5893(2) 0.49677(11) 0.2730(3) 0.0631(6) Uani d . 1 1
C C1 0.5549(3) 0.43506(16) 0.2223(4) 0.0481(8) Uani d . 1 1
C C2 0.5846(3) 0.35719(15) 0.2880(4) 0.0415(7) Uani d . 1 1
C C3 0.5159(2) 0.30486(15) 0.1807(4) 0.0424(7) Uani d . 1 1
C C4 0.4489(3) 0.34850(16) 0.0692(4) 0.0500(8) Uani d . 1 1
C C5 0.3681(3) 0.3183(2) -0.0444(5) 0.0695(10) Uani d . 1 1
H H5 0.3233 0.3490 -0.1167 0.083 Uiso calc R 1 1
C C6 0.3564(3) 0.2406(2) -0.0468(5) 0.0728(11) Uani d . 1 1
H H6 0.3012 0.2184 -0.1206 0.087 Uiso calc R 1 1
C C7 0.4244(3) 0.19516(18) 0.0577(5) 0.0612(9) Uani d . 1 1
H H7 0.4163 0.1428 0.0513 0.073 Uiso calc R 1 1
C C8 0.5051(3) 0.22649(16) 0.1725(5) 0.0523(8) Uani d . 1 1
H H8 0.5511 0.1956 0.2428 0.063 Uiso calc R 1 1
C C9 0.6510(2) 0.34259(15) 0.4264(4) 0.0432(7) Uani d . 1 1
C C10 0.6611(2) 0.26418(15) 0.4946(4) 0.0413(7) Uani d . 1 1
C C11 0.7606(3) 0.22020(16) 0.4565(4) 0.0549(9) Uani d . 1 1
H H11 0.8228 0.2403 0.3912 0.066 Uiso calc R 1 1
C C12 0.7683(3) 0.14681(17) 0.5144(5) 0.0624(10) Uani d . 1 1
H H12 0.8355 0.1176 0.4873 0.075 Uiso calc R 1 1
C C13 0.6788(3) 0.11674(17) 0.6108(5) 0.0607(9) Uani d . 1 1
H H13 0.6844 0.0671 0.6496 0.073 Uiso calc R 1 1
C C14 0.5802(3) 0.15989(18) 0.6504(5) 0.0643(10) Uani d . 1 1
H H14 0.5187 0.1393 0.7162 0.077 Uiso calc R 1 1
C C15 0.5712(3) 0.23353(16) 0.5939(4) 0.0553(8) Uani d . 1 1
H H15 0.5042 0.2626 0.6230 0.066 Uiso calc R 1 1
C C16 0.7198(3) 0.40090(16) 0.5234(4) 0.0458(8) Uani d . 1 1
C C17 0.6978(3) 0.41196(17) 0.6938(4) 0.0562(9) Uani d . 1 1
H H17 0.6395 0.3828 0.7480 0.067 Uiso calc R 1 1
C C18 0.7609(4) 0.46540(19) 0.7850(5) 0.0704(10) Uani d . 1 1
H H18 0.7447 0.4725 0.8997 0.085 Uiso calc R 1 1
C C19 0.8472(3) 0.50795(19) 0.7065(6) 0.0702(11) Uani d . 1 1
H H19 0.8891 0.5445 0.7677 0.084 Uiso calc R 1 1
C C20 0.8726(3) 0.49722(19) 0.5391(6) 0.0711(11) Uani d . 1 1
H H20 0.9326 0.5258 0.4868 0.085 Uiso calc R 1 1
C C21 0.8093(3) 0.44404(17) 0.4473(5) 0.0611(9) Uani d . 1 1
H H21 0.8267 0.4370 0.3330 0.073 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 0.0000 '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
C1 N1 C4 111.7(2)
C1 N1 H1 124.1
C4 N1 H1 124.1
O1 C1 N1 124.5(3)
O1 C1 C2 129.3(3)
N1 C1 C2 106.1(3)
C9 C2 C3 129.3(2)
C9 C2 C1 125.1(3)
C3 C2 C1 105.3(2)
C4 C3 C8 118.6(3)
C4 C3 C2 107.1(2)
C8 C3 C2 134.4(3)
C5 C4 C3 123.2(3)
C5 C4 N1 127.1(3)
C3 C4 N1 109.7(3)
C4 C5 C6 117.2(3)
C4 C5 H5 121.4
C6 C5 H5 121.4
C7 C6 C5 121.4(3)
C7 C6 H6 119.3
C5 C6 H6 119.3
C6 C7 C8 120.8(3)
C6 C7 H7 119.6
C8 C7 H7 119.6
C7 C8 C3 118.9(3)
C7 C8 H8 120.6
C3 C8 H8 120.6
C2 C9 C10 120.9(3)
C2 C9 C16 124.4(3)
C10 C9 C16 114.7(3)
C15 C10 C11 118.7(3)
C15 C10 C9 121.1(2)
C11 C10 C9 120.3(3)
C12 C11 C10 120.4(3)
C12 C11 H11 119.8
C10 C11 H11 119.8
C13 C12 C11 120.6(3)
C13 C12 H12 119.7
C11 C12 H12 119.7
C12 C13 C14 119.5(3)
C12 C13 H13 120.2
C14 C13 H13 120.2
C13 C14 C15 120.7(3)
C13 C14 H14 119.7
C15 C14 H14 119.7
C10 C15 C14 120.1(3)
C10 C15 H15 119.9
C14 C15 H15 119.9
C17 C16 C21 118.0(3)
C17 C16 C9 120.5(3)
C21 C16 C9 121.5(3)
C18 C17 C16 121.1(3)
C18 C17 H17 119.4
C16 C17 H17 119.4
C19 C18 C17 119.7(4)
C19 C18 H18 120.1
C17 C18 H18 120.1
C20 C19 C18 120.5(4)
C20 C19 H19 119.8
C18 C19 H19 119.8
C19 C20 C21 119.9(4)
C19 C20 H20 120.0
C21 C20 H20 120.0
C20 C21 C16 120.7(4)
C20 C21 H21 119.6
C16 C21 H21 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.353(4)
N1 C4 1.392(4)
N1 H1 0.8600
O1 C1 1.221(3)
C1 C2 1.505(4)
C2 C9 1.341(4)
C2 C3 1.465(4)
C3 C4 1.384(4)
C3 C8 1.390(4)
C4 C5 1.374(4)
C5 C6 1.377(5)
C5 H5 0.9300
C6 C7 1.374(5)
C6 H6 0.9300
C7 C8 1.386(4)
C7 H7 0.9300
C8 H8 0.9300
C9 C10 1.489(4)
C9 C16 1.491(4)
C10 C15 1.377(4)
C10 C11 1.380(4)
C11 C12 1.376(4)
C11 H11 0.9300
C12 C13 1.356(4)
C12 H12 0.9300
C13 C14 1.366(4)
C13 H13 0.9300
C14 C15 1.377(4)
C14 H14 0.9300
C15 H15 0.9300
C16 C17 1.379(4)
C16 C21 1.386(4)
C17 C18 1.376(4)
C17 H17 0.9300
C18 C19 1.364(5)
C18 H18 0.9300
C19 C20 1.363(6)
C19 H19 0.9300
C20 C21 1.377(5)
C20 H20 0.9300
C21 H21 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
N1 H1 O1 2_664 0.86 2.23 2.974(3) 144 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
C4 N1 C1 O1 -177.5(3)
C4 N1 C1 C2 -0.1(3)
O1 C1 C2 C9 4.6(5)
N1 C1 C2 C9 -172.6(3)
O1 C1 C2 C3 178.8(3)
N1 C1 C2 C3 1.6(3)
C9 C2 C3 C4 171.4(3)
C1 C2 C3 C4 -2.5(3)
C9 C2 C3 C8 -7.5(6)
C1 C2 C3 C8 178.6(3)
C8 C3 C4 C5 2.9(5)
C2 C3 C4 C5 -176.2(3)
C8 C3 C4 N1 -178.4(3)
C2 C3 C4 N1 2.5(3)
C1 N1 C4 C5 177.1(3)
C1 N1 C4 C3 -1.6(4)
C3 C4 C5 C6 -1.1(5)
N1 C4 C5 C6 -179.5(3)
C4 C5 C6 C7 -1.3(6)
C5 C6 C7 C8 1.8(6)
C6 C7 C8 C3 0.1(5)
C4 C3 C8 C7 -2.4(5)
C2 C3 C8 C7 176.4(3)
C3 C2 C9 C10 -1.3(5)
C1 C2 C9 C10 171.5(3)
C3 C2 C9 C16 178.4(3)
C1 C2 C9 C16 -8.8(4)
C2 C9 C10 C15 -80.4(4)
C16 C9 C10 C15 99.8(3)
C2 C9 C10 C11 98.5(3)
C16 C9 C10 C11 -81.3(3)
C15 C10 C11 C12 1.1(4)
C9 C10 C11 C12 -177.8(3)
C10 C11 C12 C13 -0.5(5)
C11 C12 C13 C14 0.0(5)
C12 C13 C14 C15 -0.2(5)
C11 C10 C15 C14 -1.3(4)
C9 C10 C15 C14 177.5(3)
C13 C14 C15 C10 0.9(5)
C2 C9 C16 C17 122.6(3)
C10 C9 C16 C17 -57.6(4)
C2 C9 C16 C21 -59.1(4)
C10 C9 C16 C21 120.6(3)
C21 C16 C17 C18 1.5(5)
C9 C16 C17 C18 179.8(3)
C16 C17 C18 C19 -0.5(5)
C17 C18 C19 C20 -0.8(6)
C18 C19 C20 C21 1.2(6)
C19 C20 C21 C16 -0.1(5)
C17 C16 C21 C20 -1.2(5)
C9 C16 C21 C20 -179.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2033558
