#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/97/2209713.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_2209713
loop_
_publ_author_name
'Xing-You Xu'
'Tong-Tao Xu'
'Shuai-Shuai Ni'
'Jian Gao'
'Da-Qi Wang'
_publ_section_title
;
 Bis{2-[1-(benzylimino)ethyl]-5-methoxyphenol}dichlorozinc(II)
;
_journal_coeditor_code           XU2055
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1548
_journal_page_last               m1549
_journal_paper_doi               10.1107/S1600536806021829
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Zn Cl2 (C16 H17 N1 O2)2]'
_chemical_formula_moiety         'C32 H34 Cl2 N2 O4 Zn'
_chemical_formula_sum            'C32 H34 Cl2 N2 O4 Zn'
_chemical_formula_weight         646.88
_chemical_name_systematic
;
Bis{2-[1-(benzylimino)ethyl]-5-methoxyphenol}dichlorozinc(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 97.928(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1785(18)
_cell_length_b                   16.082(3)
_cell_length_c                   17.555(3)
_cell_measurement_reflns_used    3722
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.7
_cell_measurement_theta_min      2.2
_cell_volume                     3125.7(9)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Bruker APEX area-dectector'
_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  0.053
_diffrn_reflns_av_sigmaI/netI    0.063
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16847
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         1.7
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.995
_exptl_absorpt_correction_T_max  0.670
_exptl_absorpt_correction_T_min  0.618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.093
_refine_ls_R_factor_gt           0.042
_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)+(0.0436P)²+1.2861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.091
_refine_ls_wR_factor_ref         0.119
_reflns_number_gt                3546
_reflns_number_total             5827
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2055.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209713
_cod_database_fobs_code          2209713
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.29374(4) 0.09695(2) 0.23116(2) 0.04291(15) Uani d . 1
Cl Cl1 0.47070(9) 0.10392(6) 0.18634(6) 0.0641(3) Uani d . 1
Cl Cl2 0.12456(10) 0.11924(6) 0.15182(6) 0.0697(3) Uani d . 1
N N1 0.4291(3) 0.30481(18) 0.36804(18) 0.0508(8) Uani d . 1
H H1 0.3970 0.2574 0.3378 0.076 Uiso d R 1
N N2 0.1462(3) -0.14823(19) 0.2369(2) 0.0589(9) Uani d . 1
H H2 0.1585 -0.0890 0.2300 0.088 Uiso d R 1
O O1 0.3161(2) 0.17401(14) 0.31878(13) 0.0501(6) Uani d . 1
O O2 -0.0102(3) 0.0823(2) 0.44542(18) 0.0821(9) Uani d . 1
O O3 0.2675(2) -0.01628(13) 0.27106(14) 0.0507(7) Uani d . 1
O O4 0.6306(3) -0.0392(2) 0.44718(18) 0.0862(10) Uani d . 1
C C1 0.3787(4) 0.3823(2) 0.4771(2) 0.0674(12) Uani d . 1
H H1A 0.4350 0.4208 0.4600 0.101 Uiso calc R 1
H H1B 0.4101 0.3619 0.5273 0.101 Uiso calc R 1
H H1C 0.3031 0.4099 0.4793 0.101 Uiso calc R 1
C C2 0.3596(3) 0.3109(2) 0.4219(2) 0.0466(9) Uani d . 1
C C3 0.2677(3) 0.2492(2) 0.4269(2) 0.0437(9) Uani d . 1
C C4 0.2475(3) 0.1829(2) 0.3732(2) 0.0441(9) Uani d . 1
C C5 0.1533(3) 0.1272(2) 0.3791(2) 0.0527(10) Uani d . 1
H H5 0.1379 0.0847 0.3431 0.063 Uiso calc R 1
C C6 0.0835(4) 0.1337(3) 0.4365(2) 0.0584(11) Uani d . 1
C C7 0.1044(4) 0.1975(3) 0.4915(2) 0.0615(11) Uani d . 1
H H7 0.0574 0.2015 0.5312 0.074 Uiso calc R 1
C C8 0.1932(4) 0.2526(3) 0.4860(2) 0.0552(10) Uani d . 1
H H8 0.2063 0.2947 0.5224 0.066 Uiso calc R 1
C C9 -0.0315(5) 0.0133(3) 0.3932(3) 0.1003(18) Uani d . 1
H H9A -0.0497 0.0337 0.3415 0.150 Uiso calc R 1
H H9B -0.0984 -0.0189 0.4060 0.150 Uiso calc R 1
H H9C 0.0394 -0.0211 0.3974 0.150 Uiso calc R 1
C C10 0.5236(4) 0.3619(2) 0.3527(2) 0.0612(11) Uani d . 1
H H10A 0.4939 0.4184 0.3550 0.073 Uiso calc R 1
H H10B 0.5414 0.3523 0.3009 0.073 Uiso calc R 1
C C11 0.6385(3) 0.3537(2) 0.4079(2) 0.0541(10) Uani d . 1
C C12 0.7082(4) 0.4230(3) 0.4273(3) 0.0667(12) Uani d . 1
H H12 0.6829 0.4746 0.4072 0.080 Uiso calc R 1
C C13 0.8150(4) 0.4163(3) 0.4762(3) 0.0816(14) Uani d . 1
H H13 0.8616 0.4636 0.4883 0.098 Uiso calc R 1
C C14 0.8534(4) 0.3423(4) 0.5069(3) 0.0909(16) Uani d . 1
H H14 0.9254 0.3386 0.5403 0.109 Uiso calc R 1
C C15 0.7849(5) 0.2733(4) 0.4882(4) 0.113(2) Uani d . 1
H H15 0.8103 0.2221 0.5090 0.135 Uiso calc R 1
C C16 0.6782(4) 0.2790(3) 0.4387(3) 0.0879(16) Uani d . 1
H H16 0.6328 0.2313 0.4260 0.105 Uiso calc R 1
C C17 0.2157(5) -0.2843(3) 0.2825(3) 0.1030(19) Uani d . 1
H H17A 0.1588 -0.2986 0.3166 0.155 Uiso calc R 1
H H17B 0.2928 -0.3085 0.3009 0.155 Uiso calc R 1
H H17C 0.1876 -0.3053 0.2320 0.155 Uiso calc R 1
C C18 0.2281(4) -0.1907(2) 0.2792(2) 0.0557(10) Uani d . 1
C C19 0.3291(3) -0.1488(2) 0.3218(2) 0.0501(10) Uani d . 1
C C20 0.3453(3) -0.0610(2) 0.3166(2) 0.0428(9) Uani d . 1
C C21 0.4466(3) -0.0241(2) 0.3592(2) 0.0488(9) Uani d . 1
H H21 0.4572 0.0331 0.3565 0.059 Uiso calc R 1
C C22 0.5298(4) -0.0706(3) 0.4045(2) 0.0601(11) Uani d . 1
C C23 0.5165(4) -0.1559(3) 0.4092(3) 0.0762(14) Uani d . 1
H H23 0.5747 -0.1874 0.4393 0.091 Uiso calc R 1
C C24 0.4189(4) -0.1931(3) 0.3699(3) 0.0715(13) Uani d . 1
H H24 0.4103 -0.2503 0.3747 0.086 Uiso calc R 1
C C25 0.6517(4) 0.0472(3) 0.4445(3) 0.0897(16) Uani d . 1
H H25A 0.6615 0.0630 0.3930 0.135 Uiso calc R 1
H H25B 0.7236 0.0608 0.4787 0.135 Uiso calc R 1
H H25C 0.5842 0.0765 0.4601 0.135 Uiso calc R 1
C C26 0.0353(4) -0.1775(3) 0.1897(3) 0.0787(14) Uani d . 1
H H26A 0.0240 -0.2362 0.1991 0.094 Uiso calc R 1
H H26B 0.0427 -0.1705 0.1357 0.094 Uiso calc R 1
C C27 -0.0723(4) -0.1297(2) 0.2084(2) 0.0524(10) Uani d . 1
C C28 -0.1043(5) -0.0562(3) 0.1728(3) 0.0766(14) Uani d . 1
H H28 -0.0586 -0.0351 0.1368 0.092 Uiso calc R 1
C C29 -0.2036(7) -0.0129(4) 0.1895(4) 0.108(2) Uani d . 1
H H29 -0.2262 0.0366 0.1640 0.129 Uiso calc R 1
C C30 -0.2680(6) -0.0427(5) 0.2434(5) 0.120(3) Uani d . 1
H H30 -0.3344 -0.0133 0.2555 0.144 Uiso calc R 1
C C31 -0.2362(5) -0.1154(5) 0.2796(3) 0.0990(19) Uani d . 1
H H31 -0.2811 -0.1358 0.3163 0.119 Uiso calc R 1
C C32 -0.1388(5) -0.1587(3) 0.2624(3) 0.0704(13) Uani d . 1
H H32 -0.1174 -0.2084 0.2877 0.085 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'
Zn Zn 0.2839 1.4301 '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
_geom_angle_publ_flag
O1 Zn1 O3 108.13(10) y
O1 Zn1 Cl2 113.27(8) y
O3 Zn1 Cl2 102.41(7) y
O1 Zn1 Cl1 102.80(8) y
O3 Zn1 Cl1 110.58(8) y
Cl1 Zn1 Cl2 119.42(5) y
C2 N1 C10 127.3(3) ?
C2 N1 H1 104.2 ?
C10 N1 H1 128.2 ?
C18 N2 C26 129.1(4) ?
C18 N2 H2 119.2 ?
C26 N2 H2 111.5 ?
C4 O1 Zn1 127.9(2) ?
C6 O2 C9 117.3(4) ?
C20 O3 Zn1 126.8(2) ?
C22 O4 C25 118.5(3) ?
C2 C1 H1A 109.5 ?
C2 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
C2 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
N1 C2 C3 119.4(3) ?
N1 C2 C1 118.7(4) ?
C3 C2 C1 121.9(4) ?
C8 C3 C4 117.3(4) ?
C8 C3 C2 120.9(3) ?
C4 C3 C2 121.8(3) ?
O1 C4 C5 120.4(3) ?
O1 C4 C3 120.6(3) ?
C5 C4 C3 118.9(4) ?
C6 C5 C4 121.4(4) ?
C6 C5 H5 119.3 ?
C4 C5 H5 119.3 ?
C5 C6 O2 124.5(4) ?
C5 C6 C7 120.5(4) ?
O2 C6 C7 114.9(4) ?
C8 C7 C6 119.0(4) ?
C8 C7 H7 120.5 ?
C6 C7 H7 120.5 ?
C7 C8 C3 122.8(4) ?
C7 C8 H8 118.6 ?
C3 C8 H8 118.6 ?
O2 C9 H9A 109.5 ?
O2 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
O2 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
N1 C10 C11 113.7(3) ?
N1 C10 H10A 108.8 ?
C11 C10 H10A 108.8 ?
N1 C10 H10B 108.8 ?
C11 C10 H10B 108.8 ?
H10A C10 H10B 107.7 ?
C16 C11 C12 118.3(4) ?
C16 C11 C10 122.3(4) ?
C12 C11 C10 119.4(4) ?
C13 C12 C11 120.2(4) ?
C13 C12 H12 119.9 ?
C11 C12 H12 119.9 ?
C14 C13 C12 121.3(5) ?
C14 C13 H13 119.4 ?
C12 C13 H13 119.4 ?
C13 C14 C15 118.9(5) ?
C13 C14 H14 120.5 ?
C15 C14 H14 120.5 ?
C14 C15 C16 120.5(5) ?
C14 C15 H15 119.8 ?
C16 C15 H15 119.8 ?
C11 C16 C15 120.8(4) ?
C11 C16 H16 119.6 ?
C15 C16 H16 119.6 ?
C18 C17 H17A 109.5 ?
C18 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C18 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
N2 C18 C19 119.7(3) ?
N2 C18 C17 119.1(4) ?
C19 C18 C17 121.2(4) ?
C24 C19 C20 116.8(4) ?
C24 C19 C18 121.2(4) ?
C20 C19 C18 122.0(3) ?
O3 C20 C21 120.9(3) ?
O3 C20 C19 120.1(3) ?
C21 C20 C19 119.0(3) ?
C22 C21 C20 121.1(4) ?
C22 C21 H21 119.4 ?
C20 C21 H21 119.4 ?
C21 C22 O4 124.4(4) ?
C21 C22 C23 120.6(4) ?
O4 C22 C23 115.0(4) ?
C24 C23 C22 119.7(4) ?
C24 C23 H23 120.2 ?
C22 C23 H23 120.2 ?
C23 C24 C19 122.8(4) ?
C23 C24 H24 118.6 ?
C19 C24 H24 118.6 ?
O4 C25 H25A 109.5 ?
O4 C25 H25B 109.5 ?
H25A C25 H25B 109.5 ?
O4 C25 H25C 109.5 ?
H25A C25 H25C 109.5 ?
H25B C25 H25C 109.5 ?
N2 C26 C27 110.6(3) ?
N2 C26 H26A 109.5 ?
C27 C26 H26A 109.5 ?
N2 C26 H26B 109.5 ?
C27 C26 H26B 109.5 ?
H26A C26 H26B 108.1 ?
C28 C27 C32 118.8(4) ?
C28 C27 C26 120.8(4) ?
C32 C27 C26 120.5(4) ?
C27 C28 C29 120.7(5) ?
C27 C28 H28 119.6 ?
C29 C28 H28 119.6 ?
C30 C29 C28 119.4(6) ?
C30 C29 H29 120.3 ?
C28 C29 H29 120.3 ?
C29 C30 C31 120.3(7) ?
C29 C30 H30 119.9 ?
C31 C30 H30 119.9 ?
C30 C31 C32 120.2(6) ?
C30 C31 H31 119.9 ?
C32 C31 H31 119.9 ?
C31 C32 C27 120.6(5) ?
C31 C32 H32 119.7 ?
C27 C32 H32 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Zn1 O1 1.964(2) y
Zn1 O3 1.987(2) y
Zn1 Cl1 2.2303(12) y
Zn1 Cl2 2.2178(11) y
N1 C2 1.308(5) y
N1 C10 1.453(5) y
N1 H1 0.9693 ?
N2 C18 1.292(5) y
N2 C26 1.470(5) y
N2 H2 0.9717 ?
O1 C4 1.312(4) ?
O2 C6 1.361(5) ?
O2 C9 1.438(5) ?
O3 C20 1.312(4) ?
O4 C22 1.361(5) ?
O4 C25 1.411(5) ?
C1 C2 1.498(5) ?
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 C3 1.440(5) ?
C3 C8 1.418(5) ?
C3 C4 1.421(5) ?
C4 C5 1.398(5) ?
C5 C6 1.360(5) ?
C5 H5 0.9300 ?
C6 C7 1.406(5) ?
C7 C8 1.344(5) ?
C7 H7 0.9300 ?
C8 H8 0.9300 ?
C9 H9A 0.9600 ?
C9 H9B 0.9600 ?
C9 H9C 0.9600 ?
C10 C11 1.506(5) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 C16 1.366(5) ?
C11 C12 1.376(5) ?
C12 C13 1.375(6) ?
C12 H12 0.9300 ?
C13 C14 1.352(7) ?
C13 H13 0.9300 ?
C14 C15 1.362(7) ?
C14 H14 0.9300 ?
C15 C16 1.379(6) ?
C15 H15 0.9300 ?
C16 H16 0.9300 ?
C17 C18 1.514(5) ?
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
C18 C19 1.433(5) ?
C19 C24 1.412(5) ?
C19 C20 1.428(5) ?
C20 C21 1.400(5) ?
C21 C22 1.361(5) ?
C21 H21 0.9300 ?
C22 C23 1.383(6) ?
C23 C24 1.348(6) ?
C23 H23 0.9300 ?
C24 H24 0.9300 ?
C25 H25A 0.9600 ?
C25 H25B 0.9600 ?
C25 H25C 0.9600 ?
C26 C27 1.501(6) ?
C26 H26A 0.9700 ?
C26 H26B 0.9700 ?
C27 C28 1.361(6) ?
C27 C32 1.365(6) ?
C28 C29 1.376(8) ?
C28 H28 0.9300 ?
C29 C30 1.353(9) ?
C29 H29 0.9300 ?
C30 C31 1.354(9) ?
C30 H30 0.9300 ?
C31 C32 1.361(7) ?
C31 H31 0.9300 ?
C32 H32 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 0.97 1.63 2.543(4) 156 y
N2 H2 O3 0.97 1.77 2.545(4) 134 y
