#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2223861.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_2223861
loop_
_publ_author_name
'Zhang, Hongming'
'Ankati, Haribabu'
'Biehl, Ed'
_publ_section_title
;
 (<i>E</i>)-3-(2,6-Dichlorobenzylidene)indolin-2-one
;
_journal_coeditor_code           IM2152
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2887
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H9 Cl2 N O'
_chemical_formula_moiety         'C15 H9 Cl2 N O'
_chemical_formula_sum            'C15 H9 Cl2 N O'
_chemical_formula_weight         290.13
_chemical_name_systematic
;
(<i>E</i>)-3-(2,6-Dichlorobenzylidene)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                99.3340(10)
_cell_angle_beta                 91.1880(10)
_cell_angle_gamma                96.3380(10)
_cell_formula_units_Z            4
_cell_length_a                   8.3908(5)
_cell_length_b                   12.6079(7)
_cell_length_c                   12.7635(7)
_cell_measurement_reflns_used    6257
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.79
_cell_volume                     1323.21(13)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       '\f and \w'
_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  0.024
_diffrn_reflns_av_sigmaI/netI    0.030
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16946
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.480
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         6459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.074
_refine_ls_R_factor_gt           0.052
_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/[\s^2^(Fo^2^)+(0.0619P)^2^+0.2428P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.121
_refine_ls_wR_factor_ref         0.134
_reflns_number_gt                4669
_reflns_number_total             6459
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    im2152.cif
_[local]_cod_data_source_block   I
_cod_original_cell_volume        1323.20(10)
_cod_database_code               2223861
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
N N1 0.8867(2) 0.59180(14) 0.44745(13) 0.0561(4) Uani d . 1
H H1 0.9144 0.5842 0.5108 0.067 Uiso calc R 1
C C2 0.9182(3) 0.52439(18) 0.35853(16) 0.0548(5) Uani d . 1
O O2 0.9914(2) 0.44512(13) 0.35421(12) 0.0729(5) Uani d . 1
C C3 0.8476(2) 0.56692(16) 0.26602(15) 0.0480(5) Uani d . 1
C C4 0.6896(3) 0.73604(17) 0.27271(17) 0.0537(5) Uani d . 1
H H4 0.6677 0.7285 0.2000 0.064 Uiso calc R 1
C C5 0.6374(3) 0.82040(18) 0.3414(2) 0.0609(6) Uani d . 1
H H5 0.5800 0.8698 0.3146 0.073 Uiso calc R 1
C C6 0.6698(3) 0.83215(18) 0.44947(19) 0.0613(6) Uani d . 1
H H6 0.6343 0.8898 0.4944 0.074 Uiso calc R 1
C C7 0.7538(3) 0.76009(18) 0.49217(17) 0.0575(5) Uani d . 1
H H7 0.7760 0.7684 0.5649 0.069 Uiso calc R 1
C C8 0.8033(2) 0.67554(16) 0.42338(16) 0.0487(5) Uani d . 1
C C9 0.7750(2) 0.66252(16) 0.31353(15) 0.0461(4) Uani d . 1
C C10 0.8627(3) 0.51431(17) 0.16770(16) 0.0520(5) Uani d . 1
H H10 0.9152 0.4526 0.1636 0.062 Uiso calc R 1
C C11 0.8090(2) 0.53923(16) 0.06520(15) 0.0478(5) Uani d . 1
C C12 0.8584(2) 0.63401(17) 0.02580(16) 0.0511(5) Uani d . 1
Cl Cl12 0.99044(8) 0.73448(5) 0.10073(5) 0.07059(19) Uani d . 1
C C13 0.8105(3) 0.6502(2) -0.07446(18) 0.0665(6) Uani d . 1
H H13 0.8441 0.7148 -0.0979 0.080 Uiso calc R 1
C C14 0.7137(3) 0.5705(3) -0.13847(19) 0.0764(8) Uani d . 1
H H14 0.6818 0.5810 -0.2059 0.092 Uiso calc R 1
C C15 0.6628(3) 0.4751(2) -0.10437(19) 0.0747(7) Uani d . 1
H H15 0.5965 0.4211 -0.1482 0.090 Uiso calc R 1
C C16 0.7111(3) 0.46028(18) -0.00474(17) 0.0570(5) Uani d . 1
Cl Cl16 0.64687(9) 0.33919(5) 0.03774(6) 0.0858(2) Uani d . 1
N N21 0.6215(2) 0.38621(13) 0.51019(13) 0.0534(4) Uani d . 1
H H21 0.6146 0.4447 0.5543 0.064 Uiso calc R 1
C C22 0.5593(3) 0.36652(16) 0.40938(16) 0.0513(5) Uani d . 1
O O22 0.4820(2) 0.42554(12) 0.36706(12) 0.0687(5) Uani d . 1
C C23 0.6022(2) 0.25727(15) 0.36049(15) 0.0461(4) Uani d . 1
C C24 0.7577(3) 0.12452(17) 0.44962(18) 0.0558(5) Uani d . 1
H H24 0.7547 0.0704 0.3904 0.067 Uiso calc R 1
C C25 0.8278(3) 0.1109(2) 0.5444(2) 0.0666(6) Uani d . 1
H H25 0.8720 0.0473 0.5491 0.080 Uiso calc R 1
C C26 0.8328(3) 0.1911(2) 0.6324(2) 0.0684(6) Uani d . 1
H H26 0.8808 0.1805 0.6957 0.082 Uiso calc R 1
C C27 0.7682(3) 0.28678(19) 0.62897(17) 0.0602(6) Uani d . 1
H H27 0.7717 0.3405 0.6885 0.072 Uiso calc R 1
C C28 0.6985(2) 0.29923(16) 0.53382(16) 0.0491(5) Uani d . 1
C C29 0.6920(2) 0.21915(15) 0.44319(15) 0.0461(4) Uani d . 1
C C30 0.5491(2) 0.21366(15) 0.26238(15) 0.0481(5) Uani d . 1
H H30 0.4870 0.2549 0.2276 0.058 Uiso calc R 1
C C31 0.5768(2) 0.10769(15) 0.20232(14) 0.0461(4) Uani d . 1
C C32 0.4491(3) 0.02878(16) 0.16894(16) 0.0518(5) Uani d . 1
Cl Cl32 0.25656(7) 0.05641(5) 0.20230(6) 0.0764(2) Uani d . 1
C C33 0.4683(3) -0.07053(18) 0.10949(18) 0.0655(6) Uani d . 1
H H33 0.3801 -0.1218 0.0890 0.079 Uiso calc R 1
C C34 0.6194(4) -0.0920(2) 0.08132(18) 0.0710(7) Uani d . 1
H H34 0.6337 -0.1587 0.0415 0.085 Uiso calc R 1
C C35 0.7498(3) -0.0170(2) 0.11093(19) 0.0692(7) Uani d . 1
H H35 0.8519 -0.0322 0.0910 0.083 Uiso calc R 1
C C36 0.7281(3) 0.08203(18) 0.17090(17) 0.0562(5) Uani d . 1
Cl Cl36 0.89345(8) 0.17731(6) 0.20621(6) 0.0860(2) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0754(12) 0.0573(11) 0.0375(9) 0.0106(9) -0.0024(8) 0.0117(8)
C2 0.0685(14) 0.0529(12) 0.0444(11) 0.0080(10) -0.0019(10) 0.0122(9)
O2 0.1095(14) 0.0638(10) 0.0513(9) 0.0352(10) -0.0080(9) 0.0110(7)
C3 0.0548(11) 0.0485(11) 0.0418(10) 0.0073(9) -0.0001(8) 0.0099(8)
C4 0.0568(12) 0.0541(12) 0.0520(12) 0.0080(10) 0.0024(9) 0.0128(10)
C5 0.0615(13) 0.0540(13) 0.0704(15) 0.0139(10) 0.0091(11) 0.0136(11)
C6 0.0663(14) 0.0517(12) 0.0647(15) 0.0066(11) 0.0176(11) 0.0042(11)
C7 0.0677(14) 0.0572(13) 0.0451(11) 0.0011(11) 0.0086(10) 0.0043(10)
C8 0.0525(11) 0.0490(11) 0.0443(11) -0.0009(9) 0.0015(8) 0.0116(9)
C9 0.0490(11) 0.0462(11) 0.0434(10) 0.0035(8) 0.0030(8) 0.0095(8)
C10 0.0614(13) 0.0488(11) 0.0481(11) 0.0164(10) -0.0007(9) 0.0084(9)
C11 0.0518(11) 0.0534(12) 0.0386(10) 0.0184(9) 0.0017(8) 0.0004(8)
C12 0.0529(12) 0.0584(12) 0.0437(11) 0.0180(10) 0.0048(9) 0.0053(9)
Cl12 0.0724(4) 0.0672(4) 0.0680(4) -0.0048(3) 0.0039(3) 0.0073(3)
C13 0.0767(16) 0.0827(17) 0.0482(13) 0.0330(14) 0.0112(11) 0.0175(12)
C14 0.0839(18) 0.109(2) 0.0389(12) 0.0392(17) -0.0063(11) 0.0035(13)
C15 0.0667(15) 0.097(2) 0.0513(14) 0.0177(14) -0.0086(11) -0.0180(14)
C16 0.0572(12) 0.0594(13) 0.0507(12) 0.0134(10) 0.0053(10) -0.0062(10)
Cl16 0.0954(5) 0.0576(4) 0.0953(5) -0.0016(3) 0.0205(4) -0.0090(3)
N21 0.0712(11) 0.0381(9) 0.0460(10) 0.0049(8) -0.0040(8) -0.0062(7)
C22 0.0656(13) 0.0391(10) 0.0470(11) 0.0052(9) 0.0022(9) 0.0009(8)
O22 0.1060(13) 0.0475(8) 0.0536(9) 0.0290(9) -0.0097(8) -0.0010(7)
C23 0.0558(11) 0.0354(9) 0.0457(11) 0.0053(8) 0.0030(9) 0.0020(8)
C24 0.0636(13) 0.0454(11) 0.0568(13) 0.0091(10) -0.0043(10) 0.0029(9)
C25 0.0698(15) 0.0580(14) 0.0739(16) 0.0116(11) -0.0136(12) 0.0158(12)
C26 0.0715(15) 0.0714(16) 0.0608(14) 0.0008(12) -0.0205(12) 0.0145(12)
C27 0.0659(14) 0.0593(13) 0.0485(12) -0.0037(11) -0.0092(10) -0.0024(10)
C28 0.0502(11) 0.0421(10) 0.0509(11) -0.0026(8) -0.0017(9) 0.0019(8)
C29 0.0488(11) 0.0423(10) 0.0454(10) 0.0008(8) -0.0010(8) 0.0046(8)
C30 0.0578(12) 0.0420(10) 0.0450(11) 0.0141(9) 0.0004(9) 0.0038(8)
C31 0.0609(12) 0.0435(10) 0.0346(9) 0.0146(9) -0.0012(8) 0.0030(8)
C32 0.0658(13) 0.0482(11) 0.0414(10) 0.0149(10) -0.0065(9) 0.0028(9)
Cl32 0.0616(4) 0.0763(4) 0.0860(5) 0.0078(3) -0.0018(3) -0.0020(3)
C33 0.0947(18) 0.0446(12) 0.0544(13) 0.0137(12) -0.0129(12) -0.0020(10)
C34 0.115(2) 0.0513(13) 0.0489(13) 0.0359(15) -0.0008(13) -0.0040(10)
C35 0.0865(18) 0.0728(16) 0.0558(13) 0.0412(14) 0.0129(12) 0.0105(12)
C36 0.0642(13) 0.0562(12) 0.0503(12) 0.0174(10) 0.0042(10) 0.0082(10)
Cl36 0.0609(4) 0.0907(5) 0.1046(6) 0.0068(3) 0.0163(4) 0.0106(4)
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'
Cl Cl 0.1484 0.1585 '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
C2 N1 C8 111.47(17)
C2 N1 H1 124.3
C8 N1 H1 124.3
O2 C2 N1 126.48(19)
O2 C2 C3 126.87(19)
N1 C2 C3 106.64(18)
C10 C3 C9 136.10(19)
C10 C3 C2 118.73(18)
C9 C3 C2 105.17(17)
C5 C4 C9 119.3(2)
C5 C4 H4 120.4
C9 C4 H4 120.4
C4 C5 C6 120.6(2)
C4 C5 H5 119.7
C6 C5 H5 119.7
C7 C6 C5 121.3(2)
C7 C6 H6 119.3
C5 C6 H6 119.3
C8 C7 C6 117.7(2)
C8 C7 H7 121.2
C6 C7 H7 121.2
C7 C8 C9 122.4(2)
C7 C8 N1 128.23(19)
C9 C8 N1 109.37(17)
C4 C9 C8 118.71(19)
C4 C9 C3 133.96(19)
C8 C9 C3 107.33(17)
C3 C10 C11 129.73(19)
C3 C10 H10 115.1
C11 C10 H10 115.1
C12 C11 C16 115.33(19)
C12 C11 C10 125.09(19)
C16 C11 C10 119.4(2)
C13 C12 C11 122.4(2)
C13 C12 Cl12 117.53(19)
C11 C12 Cl12 120.03(16)
C14 C13 C12 119.5(2)
C14 C13 H13 120.3
C12 C13 H13 120.3
C13 C14 C15 120.7(2)
C13 C14 H14 119.7
C15 C14 H14 119.7
C14 C15 C16 119.2(2)
C14 C15 H15 120.4
C16 C15 H15 120.4
C15 C16 C11 122.9(2)
C15 C16 Cl16 118.9(2)
C11 C16 Cl16 118.12(17)
C22 N21 C28 111.48(16)
C22 N21 H21 124.3
C28 N21 H21 124.3
O22 C22 N21 126.61(19)
O22 C22 C23 126.87(19)
N21 C22 C23 106.52(18)
C30 C23 C29 133.96(18)
C30 C23 C22 120.05(18)
C29 C23 C22 105.84(16)
C25 C24 C29 119.5(2)
C25 C24 H24 120.2
C29 C24 H24 120.2
C24 C25 C26 120.4(2)
C24 C25 H25 119.8
C26 C25 H25 119.8
C25 C26 C27 121.7(2)
C25 C26 H26 119.2
C27 C26 H26 119.2
C28 C27 C26 117.3(2)
C28 C27 H27 121.4
C26 C27 H27 121.4
C27 C28 C29 122.23(19)
C27 C28 N21 128.52(19)
C29 C28 N21 109.23(17)
C24 C29 C28 118.90(18)
C24 C29 C23 134.09(18)
C28 C29 C23 106.90(17)
C23 C30 C31 127.71(18)
C23 C30 H30 116.1
C31 C30 H30 116.1
C32 C31 C36 116.07(18)
C32 C31 C30 120.65(18)
C36 C31 C30 123.21(19)
C33 C32 C31 122.9(2)
C33 C32 Cl32 118.52(19)
C31 C32 Cl32 118.61(15)
C34 C33 C32 118.8(2)
C34 C33 H33 120.6
C32 C33 H33 120.6
C33 C34 C35 121.0(2)
C33 C34 H34 119.5
C35 C34 H34 119.5
C34 C35 C36 119.3(2)
C34 C35 H35 120.3
C36 C35 H35 120.3
C35 C36 C31 122.0(2)
C35 C36 Cl36 118.96(19)
C31 C36 Cl36 119.08(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.353(3)
N1 C8 1.399(3)
N1 H1 0.8600
C2 O2 1.224(2)
C2 C3 1.510(3)
C3 C10 1.336(3)
C3 C9 1.460(3)
C4 C5 1.381(3)
C4 C9 1.390(3)
C4 H4 0.9300
C5 C6 1.381(3)
C5 H5 0.9300
C6 C7 1.380(3)
C6 H6 0.9300
C7 C8 1.375(3)
C7 H7 0.9300
C8 C9 1.397(3)
C10 C11 1.468(3)
C10 H10 0.9300
C11 C12 1.395(3)
C11 C16 1.401(3)
C12 C13 1.386(3)
C12 Cl12 1.732(2)
C13 C14 1.365(4)
C13 H13 0.9300
C14 C15 1.372(4)
C14 H14 0.9300
C15 C16 1.374(3)
C15 H15 0.9300
C16 Cl16 1.736(3)
N21 C22 1.353(3)
N21 C28 1.403(3)
N21 H21 0.8600
C22 O22 1.220(3)
C22 C23 1.502(3)
C23 C30 1.330(3)
C23 C29 1.457(3)
C24 C25 1.378(3)
C24 C29 1.382(3)
C24 H24 0.9300
C25 C26 1.381(3)
C25 H25 0.9300
C26 C27 1.383(3)
C26 H26 0.9300
C27 C28 1.376(3)
C27 H27 0.9300
C28 C29 1.402(3)
C30 C31 1.473(3)
C30 H30 0.9300
C31 C32 1.389(3)
C31 C36 1.395(3)
C32 C33 1.382(3)
C32 Cl32 1.737(2)
C33 C34 1.369(4)
C33 H33 0.9300
C34 C35 1.369(4)
C34 H34 0.9300
C35 C36 1.387(3)
C35 H35 0.9300
C36 Cl36 1.733(2)
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
N21 H21 O22 2_666 0.86 2.03 2.854(2) 159.2
N1 H1 O2 2_766 0.86 1.99 2.837(2) 170.5