#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/75/2217536.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_2217536
loop_
_publ_author_name
'Ali, Hapipah M.'
'Mohamed Mustafa, M. I'
'Rizal, Mohd. Razali'
'Ng, Seik Weng'
_publ_section_title
Bis{4-chloro-2-[2-(1H-indol-3-yl)ethyliminomethyl]phenolato-κ²N,O}zinc(II)
_journal_coeditor_code           HG2370
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m421
_journal_page_last               m421
_journal_paper_doi               10.1107/S1600536808002213
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Zn (C17 H14 Cl N2 O)2]'
_chemical_formula_moiety         'C34 H28 Cl2 N4 O2 Zn'
_chemical_formula_sum            'C34 H28 Cl2 N4 O2 Zn'
_chemical_formula_weight         660.87
_chemical_name_systematic
;
Bis{4-chloro-2-[2-(1H-indol-3-yl)ethyliminomethyl]phenolato-
κ²N,O}zinc(II)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 91.8010(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.8989(3)
_cell_length_b                   5.49600(10)
_cell_length_c                   20.6138(3)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    128(2)
_cell_measurement_theta_max      31.2
_cell_measurement_theta_min      2.5
_cell_volume                     2932.73(8)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      139(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'medium-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17664
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.059
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_correction_T_min  0.714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.558
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3352
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.206
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0632P)²+1.1156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0997
_reflns_number_gt                3023
_reflns_number_total             3352
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2370.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2217536
_cod_database_fobs_code          2217536
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'
'-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
Zn Zn1 0.5000 0.49480(5) 0.7500 0.01823(11) Uani d S 1
Cl Cl1 0.39490(2) 0.33657(10) 0.42675(2) 0.03469(14) Uani d . 1
O O1 0.46240(5) 0.6771(2) 0.68555(6) 0.0256(3) Uani d . 1
N N1 0.53085(5) 0.2579(3) 0.68736(6) 0.0167(3) Uani d . 1
C C1 0.45075(6) 0.5975(3) 0.62688(7) 0.0175(3) Uani d . 1
N N2 0.71557(6) -0.2875(3) 0.76815(7) 0.0235(3) Uani d D 1
C C2 0.41428(7) 0.7308(3) 0.58836(8) 0.0226(3) Uani d D 1
C C3 0.39787(7) 0.6548(3) 0.52766(8) 0.0230(3) Uani d D 1
C C4 0.41765(7) 0.4409(4) 0.50234(8) 0.0216(3) Uani d . 1
C C5 0.45433(7) 0.3096(3) 0.53648(8) 0.0206(3) Uani d D 1
C C6 0.47188(6) 0.3836(3) 0.59882(7) 0.0167(3) Uani d . 1
C C7 0.51092(6) 0.2301(3) 0.63013(8) 0.0181(3) Uani d D 1
C C8 0.56967(6) 0.0809(3) 0.71064(8) 0.0186(3) Uani d D 1
C C9 0.62386(7) 0.1885(4) 0.70984(11) 0.0305(4) Uani d D 1
C C10 0.66211(7) 0.0247(3) 0.74448(10) 0.0233(4) Uani d . 1
C C11 0.68435(7) -0.1805(3) 0.72056(9) 0.0245(4) Uani d D 1
C C12 0.68028(6) 0.0477(3) 0.81090(9) 0.0209(3) Uani d . 1
C C13 0.67219(7) 0.2182(4) 0.86012(10) 0.0296(4) Uani d D 1
C C15 0.69689(9) 0.1852(4) 0.91969(10) 0.0359(5) Uani d D 1
C C16 0.72995(9) -0.0135(4) 0.93160(11) 0.0344(5) Uani d D 1
C C17 0.73904(7) -0.1845(4) 0.88415(9) 0.0279(4) Uani d D 1
C C18 0.71359(6) -0.1517(3) 0.82397(8) 0.0205(3) Uani d . 1
H H2N 0.7331(9) -0.421(3) 0.7639(13) 0.042(7) Uiso d D 1
H H2 0.3996(9) 0.884(3) 0.6056(11) 0.036(6) Uiso d D 1
H H3 0.3712(7) 0.753(4) 0.5031(10) 0.033(6) Uiso d D 1
H H5 0.4670(8) 0.155(3) 0.5170(11) 0.036(6) Uiso d D 1
H H7 0.5240(7) 0.097(3) 0.6024(8) 0.017(5) Uiso d D 1
H H81 0.5617(8) 0.033(3) 0.7554(6) 0.018(5) Uiso d D 1
H H82 0.5676(9) -0.067(3) 0.6831(10) 0.028(5) Uiso d D 1
H H91 0.6237(11) 0.351(3) 0.7316(12) 0.052(8) Uiso d D 1
H H92 0.6344(10) 0.217(5) 0.6640(6) 0.048(8) Uiso d D 1
H H11 0.6818(9) -0.251(4) 0.6764(6) 0.034(6) Uiso d D 1
H H13 0.6501(8) 0.365(3) 0.8521(11) 0.038(6) Uiso d D 1
H H15 0.6893(9) 0.299(4) 0.9553(9) 0.037(6) Uiso d D 1
H H16 0.7477(10) -0.026(5) 0.9748(8) 0.045(8) Uiso d D 1
H H17 0.7634(8) -0.323(3) 0.8917(12) 0.041(7) Uiso d 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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
O1 Zn1 O1 . 2_656 116.62(8) yes
O1 Zn1 N1 . . 95.57(5) yes
O1 Zn1 N1 . 2_656 125.55(6) yes
O1 Zn1 N1 2_656 . 125.55(6) ?
O1 Zn1 N1 2_656 2_656 95.57(5) ?
N1 Zn1 N1 . 2_656 99.56(8) yes
C1 O1 Zn1 . . 124.38(11) ?
C7 N1 C8 . . 118.25(14) ?
C7 N1 Zn1 . . 120.68(11) ?
C8 N1 Zn1 . . 119.96(10) ?
O1 C1 C2 . . 118.25(15) ?
O1 C1 C6 . . 124.63(15) ?
C2 C1 C6 . . 117.12(14) ?
C18 N2 C11 . . 109.06(15) ?
C18 N2 H2N . . 125.3(18) ?
C11 N2 H2N . . 125.7(18) ?
C3 C2 C1 . . 122.28(16) ?
C3 C2 H2 . . 118.2(14) ?
C1 C2 H2 . . 119.6(14) ?
C2 C3 C4 . . 119.47(15) ?
C2 C3 H3 . . 119.0(14) ?
C4 C3 H3 . . 121.5(14) ?
C5 C4 C3 . . 120.68(16) ?
C5 C4 Cl1 . . 119.65(14) ?
C3 C4 Cl1 . . 119.66(13) ?
C4 C5 C6 . . 120.98(16) ?
C4 C5 H5 . . 118.2(14) ?
C6 C5 H5 . . 120.8(14) ?
C5 C6 C1 . . 119.38(14) ?
C5 C6 C7 . . 115.93(14) ?
C1 C6 C7 . . 124.69(14) ?
N1 C7 C6 . . 126.44(15) ?
N1 C7 H7 . . 118.8(12) ?
C6 C7 H7 . . 114.6(12) ?
N1 C8 C9 . . 111.15(14) ?
N1 C8 H81 . . 108.7(12) ?
C9 C8 H81 . . 109.5(12) ?
N1 C8 H82 . . 109.4(14) ?
C9 C8 H82 . . 110.3(13) ?
H81 C8 H82 . . 107.8(18) ?
C10 C9 C8 . . 110.87(15) ?
C10 C9 H91 . . 109.5(17) ?
C8 C9 H91 . . 109.0(16) ?
C10 C9 H92 . . 110.3(16) ?
C8 C9 H92 . . 110.3(15) ?
H91 C9 H92 . . 107(2) ?
C11 C10 C12 . . 106.68(16) ?
C11 C10 C9 . . 127.04(19) ?
C12 C10 C9 . . 126.20(17) ?
C10 C11 N2 . . 109.81(16) ?
C10 C11 H11 . . 129.7(14) ?
N2 C11 H11 . . 120.4(14) ?
C13 C12 C18 . . 118.94(17) ?
C13 C12 C10 . . 134.06(17) ?
C18 C12 C10 . . 106.99(15) ?
C15 C13 C12 . . 118.76(19) ?
C15 C13 H13 . . 120.0(14) ?
C12 C13 H13 . . 121.2(14) ?
C13 C15 C16 . . 121.40(19) ?
C13 C15 H15 . . 118.7(15) ?
C16 C15 H15 . . 119.8(15) ?
C17 C16 C15 . . 121.4(2) ?
C17 C16 H16 . . 120.4(16) ?
C15 C16 H16 . . 118.2(16) ?
C16 C17 C18 . . 117.02(18) ?
C16 C17 H17 . . 121.9(15) ?
C18 C17 H17 . . 121.1(15) ?
N2 C18 C17 . . 130.10(17) ?
N2 C18 C12 . . 107.45(15) ?
C17 C18 C12 . . 122.43(17) ?
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
Zn1 O1 . 1.9070(10) yes
Zn1 O1 2_656 1.9070(10) ?
Zn1 N1 . 2.0160(10) yes
Zn1 N1 2_656 2.0160(10) ?
Cl1 C4 . 1.745(2) ?
O1 C1 . 1.312(2) ?
N1 C7 . 1.282(2) ?
N1 C8 . 1.469(2) ?
C1 C2 . 1.419(2) ?
C1 C6 . 1.427(2) ?
N2 C18 . 1.374(2) ?
N2 C11 . 1.383(2) ?
N2 H2N . 0.870(10) ?
C2 C3 . 1.374(2) ?
C2 H2 . 0.994(10) ?
C3 C4 . 1.391(3) ?
C3 H3 . 1.001(10) ?
C4 C5 . 1.370(2) ?
C5 C6 . 1.410(2) ?
C5 H5 . 0.999(10) ?
C6 C7 . 1.453(2) ?
C7 H7 . 0.994(9) ?
C8 C9 . 1.523(2) ?
C8 H81 . 0.989(9) ?
C8 H82 . 0.994(10) ?
C9 C10 . 1.502(2) ?
C9 H91 . 0.998(10) ?
C9 H92 . 1.004(10) ?
C10 C11 . 1.366(3) ?
C10 C12 . 1.439(3) ?
C11 H11 . 0.990(10) ?
C12 C13 . 1.402(3) ?
C12 C18 . 1.415(2) ?
C13 C15 . 1.379(3) ?
C13 H13 . 0.998(10) ?
C15 C16 . 1.405(3) ?
C15 H15 . 0.990(10) ?
C16 C17 . 1.382(3) ?
C16 H16 . 0.992(10) ?
C17 C18 . 1.398(2) ?
C17 H17 . 0.996(10) ?
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
O1 Zn1 O1 C1 2_656 153.77(15)
N1 Zn1 O1 C1 . 19.16(14)
N1 Zn1 O1 C1 2_656 -86.78(15)
O1 Zn1 N1 C7 . -18.84(14)
O1 Zn1 N1 C7 2_656 -147.38(12)
N1 Zn1 N1 C7 2_656 108.67(14)
O1 Zn1 N1 C8 . 173.41(12)
O1 Zn1 N1 C8 2_656 44.87(14)
N1 Zn1 N1 C8 2_656 -59.09(10)
Zn1 O1 C1 C2 . 167.80(12)
Zn1 O1 C1 C6 . -11.6(2)
O1 C1 C2 C3 . -176.76(17)
C6 C1 C2 C3 . 2.7(3)
C1 C2 C3 C4 . -0.4(3)
C2 C3 C4 C5 . -1.9(3)
C2 C3 C4 Cl1 . 177.25(14)
C3 C4 C5 C6 . 1.8(3)
Cl1 C4 C5 C6 . -177.31(13)
C4 C5 C6 C1 . 0.5(3)
C4 C5 C6 C7 . -179.84(16)
O1 C1 C6 C5 . 176.72(16)
C2 C1 C6 C5 . -2.7(2)
O1 C1 C6 C7 . -2.9(3)
C2 C1 C6 C7 . 177.69(15)
C8 N1 C7 C6 . 179.43(15)
Zn1 N1 C7 C6 . 11.5(2)
C5 C6 C7 N1 . -177.31(16)
C1 C6 C7 N1 . 2.3(3)
C7 N1 C8 C9 . 104.80(18)
Zn1 N1 C8 C9 . -87.15(16)
N1 C8 C9 C10 . 169.91(16)
C8 C9 C10 C11 . 79.8(2)
C8 C9 C10 C12 . -96.6(2)
C12 C10 C11 N2 . -0.1(2)
C9 C10 C11 N2 . -177.12(16)
C18 N2 C11 C10 . 0.3(2)
C11 C10 C12 C13 . 178.99(19)
C9 C10 C12 C13 . -4.0(3)
C11 C10 C12 C18 . -0.05(19)
C9 C10 C12 C18 . 176.96(16)
C18 C12 C13 C15 . -0.2(3)
C10 C12 C13 C15 . -179.14(19)
C12 C13 C15 C16 . 0.4(3)
C13 C15 C16 C17 . -0.1(3)
C15 C16 C17 C18 . -0.4(3)
C11 N2 C18 C17 . -178.80(18)
C11 N2 C18 C12 . -0.31(19)
C16 C17 C18 N2 . 178.95(18)
C16 C17 C18 C12 . 0.7(3)
C13 C12 C18 N2 . -178.99(16)
C10 C12 C18 N2 . 0.22(19)
C13 C12 C18 C17 . -0.4(3)
C10 C12 C18 C17 . 178.85(16)
