#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/73/2227312.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_2227312
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Goh, Jia Hao'
'Yu, Haitao'
'Zhang, Yan'
_publ_section_title
;
 (Z)-1-Acetyl-3-[2-oxo-1-phenyl-2-(3-pyridyl)ethylidene]indolin-2-one
;
_journal_coeditor_code           CI5150
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2232
_journal_page_last               o2233
_journal_paper_doi               10.1107/S1600536810030874
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C23 H16 N2 O3'
_chemical_formula_moiety         'C23 H16 N2 O3'
_chemical_formula_sum            'C23 H16 N2 O3'
_chemical_formula_weight         368.38
_chemical_name_systematic
;
(Z)-1-Acetyl-3-[2-oxo-1-phenyl-2-(3-pyridyl)ethylidene]indolin-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                84.804(7)
_cell_angle_beta                 87.064(7)
_cell_angle_gamma                76.843(6)
_cell_formula_units_Z            2
_cell_length_a                   7.9259(19)
_cell_length_b                   9.086(2)
_cell_length_c                   12.431(3)
_cell_measurement_reflns_used    7658
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      32.12
_cell_measurement_theta_min      2.31
_cell_volume                     867.7(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
;
Bruker APEXII DUO CCD area-detector
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19600
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.65
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.163
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         5017
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0399
_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)+(0.0637P)²+0.2808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1156
_reflns_number_gt                4237
_reflns_number_total             5017
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5150.cif
_cod_data_source_block           I
_cod_database_code               2227312
_cod_database_fobs_code          2227312
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.74656(11) 0.64928(9) 0.08150(6) 0.01988(17) Uani d . 1 . .
O O2 0.94194(10) 0.51863(9) 0.29214(7) 0.01842(17) Uani d . 1 . .
O O3 0.61891(12) 0.98853(10) -0.16758(7) 0.02319(19) Uani d . 1 . .
N N1 0.72823(12) 0.89175(10) -0.00538(7) 0.01472(18) Uani d . 1 . .
N N2 0.48355(13) 0.38455(11) 0.38814(8) 0.0208(2) Uani d . 1 . .
C C1 0.80969(13) 1.00838(12) 0.13505(8) 0.01429(19) Uani d . 1 . .
C C2 0.86200(14) 1.12405(12) 0.18121(9) 0.0175(2) Uani d . 1 . .
H H2A 0.8958 1.1110 0.2526 0.021 Uiso calc R 1 . .
C C3 0.86325(15) 1.25906(13) 0.11949(10) 0.0200(2) Uani d . 1 . .
H H3A 0.8961 1.3375 0.1501 0.024 Uiso calc R 1 . .
C C4 0.81564(16) 1.27772(13) 0.01211(10) 0.0220(2) Uani d . 1 . .
H H4A 0.8160 1.3692 -0.0279 0.026 Uiso calc R 1 . .
C C5 0.76744(15) 1.16211(13) -0.03661(9) 0.0199(2) Uani d . 1 . .
H H5A 0.7379 1.1742 -0.1088 0.024 Uiso calc R 1 . .
C C6 0.76495(13) 1.02835(12) 0.02614(8) 0.0149(2) Uani d . 1 . .
C C7 0.75826(13) 0.77964(12) 0.08245(8) 0.01466(19) Uani d . 1 . .
C C8 0.79925(13) 0.85485(11) 0.17647(8) 0.01383(19) Uani d . 1 . .
C C9 0.80773(13) 0.78123(11) 0.27615(8) 0.01317(19) Uani d . 1 . .
C C10 0.80593(13) 0.61403(11) 0.29125(8) 0.01361(19) Uani d . 1 . .
C C11 0.63598(13) 0.57473(11) 0.31789(8) 0.01344(19) Uani d . 1 . .
C C12 0.47958(14) 0.67902(12) 0.29924(9) 0.0165(2) Uani d . 1 . .
H H12A 0.4784 0.7776 0.2711 0.020 Uiso calc R 1 . .
C C13 0.32642(14) 0.63324(13) 0.32333(9) 0.0187(2) Uani d . 1 . .
H H13A 0.2201 0.6996 0.3104 0.022 Uiso calc R 1 . .
C C14 0.33486(14) 0.48613(13) 0.36719(9) 0.0192(2) Uani d . 1 . .
H H14A 0.2312 0.4559 0.3831 0.023 Uiso calc R 1 . .
C C15 0.63067(14) 0.42976(12) 0.36275(9) 0.0170(2) Uani d . 1 . .
H H15A 0.7352 0.3606 0.3757 0.020 Uiso calc R 1 . .
C C16 0.80906(13) 0.84819(11) 0.38002(8) 0.01300(19) Uani d . 1 . .
C C17 0.90394(13) 0.76491(12) 0.46632(8) 0.0148(2) Uani d . 1 . .
H H17A 0.9728 0.6691 0.4568 0.018 Uiso calc R 1 . .
C C18 0.89565(14) 0.82461(12) 0.56573(9) 0.0164(2) Uani d . 1 . .
H H18A 0.9591 0.7688 0.6226 0.020 Uiso calc R 1 . .
C C19 0.79292(14) 0.96743(12) 0.58082(9) 0.0173(2) Uani d . 1 . .
H H19A 0.7894 1.0079 0.6472 0.021 Uiso calc R 1 . .
C C20 0.69532(14) 1.04977(12) 0.49644(9) 0.0169(2) Uani d . 1 . .
H H20A 0.6253 1.1448 0.5068 0.020 Uiso calc R 1 . .
C C21 0.70218(13) 0.99052(12) 0.39705(9) 0.0150(2) Uani d . 1 . .
H H21A 0.6355 1.0455 0.3412 0.018 Uiso calc R 1 . .
C C22 0.66296(14) 0.87655(13) -0.10556(9) 0.0168(2) Uani d . 1 . .
C C23 0.65025(17) 0.72265(14) -0.13229(10) 0.0238(2) Uani d . 1 . .
H H23D 0.6085 0.7288 -0.2041 0.036 Uiso calc R 1 . .
H H23A 0.5715 0.6849 -0.0817 0.036 Uiso calc R 1 . .
H H23B 0.7626 0.6552 -0.1283 0.036 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C22 N1 C7 . . 126.23(9) ?
C22 N1 C6 . . 124.62(9) ?
C7 N1 C6 . . 109.05(8) ?
C15 N2 C14 . . 116.88(10) ?
C2 C1 C6 . . 119.44(10) ?
C2 C1 C8 . . 132.38(10) ?
C6 C1 C8 . . 108.08(9) ?
C3 C2 C1 . . 119.30(10) ?
C3 C2 H2A . . 120.3 ?
C1 C2 H2A . . 120.3 ?
C2 C3 C4 . . 120.41(10) ?
C2 C3 H3A . . 119.8 ?
C4 C3 H3A . . 119.8 ?
C3 C4 C5 . . 121.29(10) ?
C3 C4 H4A . . 119.4 ?
C5 C4 H4A . . 119.4 ?
C6 C5 C4 . . 117.78(11) ?
C6 C5 H5A . . 121.1 ?
C4 C5 H5A . . 121.1 ?
C5 C6 C1 . . 121.74(10) ?
C5 C6 N1 . . 128.68(10) ?
C1 C6 N1 . . 109.51(9) ?
O1 C7 N1 . . 126.06(10) ?
O1 C7 C8 . . 127.05(10) ?
N1 C7 C8 . . 106.84(9) ?
C9 C8 C1 . . 133.76(10) ?
C9 C8 C7 . . 119.91(10) ?
C1 C8 C7 . . 106.16(9) ?
C8 C9 C16 . . 126.82(10) ?
C8 C9 C10 . . 120.64(9) ?
C16 C9 C10 . . 112.44(9) ?
O2 C10 C11 . . 122.38(10) ?
O2 C10 C9 . . 120.09(9) ?
C11 C10 C9 . . 117.10(9) ?
C15 C11 C12 . . 118.37(10) ?
C15 C11 C10 . . 119.66(9) ?
C12 C11 C10 . . 121.97(9) ?
C13 C12 C11 . . 118.78(10) ?
C13 C12 H12A . . 120.6 ?
C11 C12 H12A . . 120.6 ?
C12 C13 C14 . . 118.45(10) ?
C12 C13 H13A . . 120.8 ?
C14 C13 H13A . . 120.8 ?
N2 C14 C13 . . 123.95(10) ?
N2 C14 H14A . . 118.0 ?
C13 C14 H14A . . 118.0 ?
N2 C15 C11 . . 123.54(10) ?
N2 C15 H15A . . 118.2 ?
C11 C15 H15A . . 118.2 ?
C17 C16 C21 . . 118.84(10) ?
C17 C16 C9 . . 120.64(9) ?
C21 C16 C9 . . 120.24(9) ?
C18 C17 C16 . . 120.34(10) ?
C18 C17 H17A . . 119.8 ?
C16 C17 H17A . . 119.8 ?
C17 C18 C19 . . 120.29(10) ?
C17 C18 H18A . . 119.9 ?
C19 C18 H18A . . 119.9 ?
C18 C19 C20 . . 119.87(10) ?
C18 C19 H19A . . 120.1 ?
C20 C19 H19A . . 120.1 ?
C21 C20 C19 . . 120.17(10) ?
C21 C20 H20A . . 119.9 ?
C19 C20 H20A . . 119.9 ?
C20 C21 C16 . . 120.45(10) ?
C20 C21 H21A . . 119.8 ?
C16 C21 H21A . . 119.8 ?
O3 C22 N1 . . 119.12(10) ?
O3 C22 C23 . . 122.22(10) ?
N1 C22 C23 . . 118.65(10) ?
C22 C23 H23D . . 109.5 ?
C22 C23 H23A . . 109.5 ?
H23D C23 H23A . . 109.5 ?
C22 C23 H23B . . 109.5 ?
H23D C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.2100(13) ?
O2 C10 . 1.2196(13) ?
O3 C22 . 1.2146(14) ?
N1 C22 . 1.4027(14) ?
N1 C7 . 1.4146(13) ?
N1 C6 . 1.4293(14) ?
N2 C15 . 1.3360(15) ?
N2 C14 . 1.3421(15) ?
C1 C2 . 1.3920(15) ?
C1 C6 . 1.4025(15) ?
C1 C8 . 1.4614(14) ?
C2 C3 . 1.3884(16) ?
C2 H2A . 0.93 ?
C3 C4 . 1.3909(17) ?
C3 H3A . 0.93 ?
C4 C5 . 1.3920(17) ?
C4 H4A . 0.93 ?
C5 C6 . 1.3868(15) ?
C5 H5A . 0.93 ?
C7 C8 . 1.4911(14) ?
C8 C9 . 1.3510(14) ?
C9 C16 . 1.4779(14) ?
C9 C10 . 1.5169(15) ?
C10 C11 . 1.4844(15) ?
C11 C15 . 1.3919(15) ?
C11 C12 . 1.3940(14) ?
C12 C13 . 1.3807(15) ?
C12 H12A . 0.93 ?
C13 C14 . 1.3854(16) ?
C13 H13A . 0.93 ?
C14 H14A . 0.93 ?
C15 H15A . 0.93 ?
C16 C17 . 1.4020(14) ?
C16 C21 . 1.4026(14) ?
C17 C18 . 1.3866(15) ?
C17 H17A . 0.93 ?
C18 C19 . 1.3890(15) ?
C18 H18A . 0.93 ?
C19 C20 . 1.3914(15) ?
C19 H19A . 0.93 ?
C20 C21 . 1.3855(15) ?
C20 H20A . 0.93 ?
C21 H21A . 0.93 ?
C22 C23 . 1.4925(16) ?
C23 H23D . 0.96 ?
C23 H23A . 0.96 ?
C23 H23B . 0.96 ?
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 O3 2_675 0.93 2.37 3.2518(16) 158 yes
C14 H14A O2 1_455 0.93 2.53 3.2381(16) 133 yes
C20 H20A N2 1_565 0.93 2.58 3.3238(17) 137 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 2.16(16) ?
C8 C1 C2 C3 . . . . 177.86(11) ?
C1 C2 C3 C4 . . . . -1.10(17) ?
C2 C3 C4 C5 . . . . -0.66(18) ?
C3 C4 C5 C6 . . . . 1.30(17) ?
C4 C5 C6 C1 . . . . -0.20(17) ?
C4 C5 C6 N1 . . . . -176.92(10) ?
C2 C1 C6 C5 . . . . -1.54(16) ?
C8 C1 C6 C5 . . . . -178.19(10) ?
C2 C1 C6 N1 . . . . 175.75(9) ?
C8 C1 C6 N1 . . . . -0.91(12) ?
C22 N1 C6 C5 . . . . -9.52(17) ?
C7 N1 C6 C5 . . . . 173.99(11) ?
C22 N1 C6 C1 . . . . 173.44(9) ?
C7 N1 C6 C1 . . . . -3.05(12) ?
C22 N1 C7 O1 . . . . 6.86(17) ?
C6 N1 C7 O1 . . . . -176.72(10) ?
C22 N1 C7 C8 . . . . -170.80(9) ?
C6 N1 C7 C8 . . . . 5.61(11) ?
C2 C1 C8 C9 . . . . 13.1(2) ?
C6 C1 C8 C9 . . . . -170.79(11) ?
C2 C1 C8 C7 . . . . -171.80(11) ?
C6 C1 C8 C7 . . . . 4.26(11) ?
O1 C7 C8 C9 . . . . -7.79(17) ?
N1 C7 C8 C9 . . . . 169.84(9) ?
O1 C7 C8 C1 . . . . 176.33(11) ?
N1 C7 C8 C1 . . . . -6.04(11) ?
C1 C8 C9 C16 . . . . 8.63(19) ?
C7 C8 C9 C16 . . . . -165.88(9) ?
C1 C8 C9 C10 . . . . -175.20(10) ?
C7 C8 C9 C10 . . . . 10.28(15) ?
C8 C9 C10 O2 . . . . 91.78(13) ?
C16 C9 C10 O2 . . . . -91.54(12) ?
C8 C9 C10 C11 . . . . -95.54(12) ?
C16 C9 C10 C11 . . . . 81.14(11) ?
O2 C10 C11 C15 . . . . 10.99(16) ?
C9 C10 C11 C15 . . . . -161.52(10) ?
O2 C10 C11 C12 . . . . -168.92(10) ?
C9 C10 C11 C12 . . . . 18.58(15) ?
C15 C11 C12 C13 . . . . -1.65(16) ?
C10 C11 C12 C13 . . . . 178.26(10) ?
C11 C12 C13 C14 . . . . 1.31(16) ?
C15 N2 C14 C13 . . . . -1.21(18) ?
C12 C13 C14 N2 . . . . 0.14(18) ?
C14 N2 C15 C11 . . . . 0.83(17) ?
C12 C11 C15 N2 . . . . 0.58(17) ?
C10 C11 C15 N2 . . . . -179.33(10) ?
C8 C9 C16 C17 . . . . -146.10(11) ?
C10 C9 C16 C17 . . . . 37.46(13) ?
C8 C9 C16 C21 . . . . 40.03(15) ?
C10 C9 C16 C21 . . . . -136.40(10) ?
C21 C16 C17 C18 . . . . -1.83(15) ?
C9 C16 C17 C18 . . . . -175.78(9) ?
C16 C17 C18 C19 . . . . 0.13(16) ?
C17 C18 C19 C20 . . . . 1.24(16) ?
C18 C19 C20 C21 . . . . -0.87(17) ?
C19 C20 C21 C16 . . . . -0.86(16) ?
C17 C16 C21 C20 . . . . 2.19(15) ?
C9 C16 C21 C20 . . . . 176.17(10) ?
C7 N1 C22 O3 . . . . 168.91(10) ?
C6 N1 C22 O3 . . . . -6.97(16) ?
C7 N1 C22 C23 . . . . -11.15(16) ?
C6 N1 C22 C23 . . . . 172.96(10) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656200
