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#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/76/1517649.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_1517649
loop_
_publ_author_name
'Ying-Ying Liu'
'Jie Liu'
'Jin Yang'
'Bo Liu'
'Jian-Fang Ma'
_publ_section_title
;
 Eight coordination compounds based on a reduced Schiff base
 tetraaminodiphenol macrocyclic ligand
;
_journal_name_full
;
Inorganica Chimica Acta
;
_journal_page_first              85
_journal_page_last               96
_journal_volume                  403
_journal_year                    2013
_chemical_formula_sum            'C16 H18 N2 O4 S Zn'
_chemical_formula_weight         399.75
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.739(2)
_cell_length_b                   9.557(4)
_cell_length_c                   20.295(4)
_cell_measurement_reflns_used    2651
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     3246.7(16)
_computing_cell_refinement       CrysAlis
_computing_data_collection       'CrysAlis (Oxford Diffraction, 2006)'
_computing_data_reduction        CrysAlis
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       'ω scan'
_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  0.0868
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            29462
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    1.665
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis (Oxford Diffraction, 2006)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3699
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0423
_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)+(0.0344P)²+3.0707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                2651
_reflns_number_total             3699
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2013-403-85-96-3.cif
_cod_data_source_block           3
_cod_database_code               1517649
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Zn1 Zn 0.93226(2) 0.00631(4) 0.054634(16) 0.02818(12) Uani 1 1 d .
C1 C 1.10445(18) 0.0558(3) 0.08727(14) 0.0301(7) Uani 1 1 d .
C2 C 1.09819(19) 0.0000(3) 0.15100(15) 0.0321(7) Uani 1 1 d .
C3 C 1.1531(2) 0.0421(4) 0.19842(15) 0.0366(8) Uani 1 1 d .
H3 H 1.1492 0.0061 0.2409 0.044 Uiso 1 1 calc R
C4 C 1.2135(2) 0.1361(4) 0.18408(15) 0.0370(8) Uani 1 1 d .
C5 C 1.21840(18) 0.1909(4) 0.12030(15) 0.0346(7) Uani 1 1 d .
H5 H 1.2588 0.2540 0.1101 0.042 Uiso 1 1 calc R
C6 C 1.16402(18) 0.1525(3) 0.07214(14) 0.0301(7) Uani 1 1 d .
C7 C 1.2747(2) 0.1779(4) 0.23558(16) 0.0514(10) Uani 1 1 d .
H7A H 1.3117 0.2433 0.2168 0.077 Uiso 1 1 calc R
H7B H 1.3030 0.0963 0.2502 0.077 Uiso 1 1 calc R
H7C H 1.2480 0.2205 0.2723 0.077 Uiso 1 1 calc R
C8 C 1.1615(2) 0.2311(4) 0.00703(15) 0.0369(8) Uani 1 1 d .
H8A H 1.1160 0.2940 0.0081 0.044 Uiso 1 1 calc R
H8B H 1.2091 0.2887 0.0043 0.044 Uiso 1 1 calc R
C9 C 1.1361(2) 0.2347(3) -0.11230(15) 0.0365(8) Uani 1 1 d .
H9A H 1.1814 0.2933 -0.1235 0.044 Uiso 1 1 calc R
H9B H 1.0916 0.2955 -0.1015 0.044 Uiso 1 1 calc R
C10 C 1.0334(2) -0.1049(3) 0.16635(16) 0.0366(8) Uani 1 1 d .
H10A H 1.0412 -0.1874 0.1393 0.044 Uiso 1 1 calc R
H10B H 1.0379 -0.1331 0.2121 0.044 Uiso 1 1 calc R
C11 C 0.8855(2) -0.1463(4) 0.17031(15) 0.0427(8) Uani 1 1 d .
H11A H 0.8391 -0.0930 0.1841 0.051 Uiso 1 1 calc R
H11B H 0.9013 -0.2062 0.2066 0.051 Uiso 1 1 calc R
C12 C 0.96994(18) 0.4030(3) 0.07630(14) 0.0273(6) Uani 1 1 d .
C13 C 1.0328(2) 0.4299(4) 0.11682(15) 0.0364(8) Uani 1 1 d .
H13 H 1.0338 0.3919 0.1590 0.044 Uiso 1 1 calc R
C14 C 1.0962(2) 0.5146(4) 0.09547(16) 0.0388(8) Uani 1 1 d .
H14 H 1.1388 0.5325 0.1237 0.047 Uiso 1 1 calc R
C15 C 1.09606(19) 0.5710(3) 0.03381(15) 0.0337(7) Uani 1 1 d .
H15 H 1.1380 0.6284 0.0207 0.040 Uiso 1 1 calc R
C16 C 1.03232(19) 0.5429(3) -0.01068(14) 0.0261(6) Uani 1 1 d .
O1 O 1.05021(13) 0.0185(3) 0.04191(10) 0.0409(6) Uani 1 1 d .
O2 O 0.87393(13) 0.1894(2) 0.06333(10) 0.0351(5) Uani 1 1 d .
O3 O 0.91532(14) 0.2567(2) 0.17329(10) 0.0407(6) Uani 1 1 d .
O4 O 0.82101(13) 0.3996(2) 0.11075(12) 0.0439(6) Uani 1 1 d .
S1 S 0.88870(5) 0.30596(8) 0.10961(4) 0.03088(19) Uani 1 1 d .
N1 N 1.15626(16) 0.1474(3) -0.05429(12) 0.0315(6) Uani 1 1 d D
H1N H 1.2019(14) 0.112(4) -0.0595(16) 0.047 Uiso 1 1 d D
N2 N 0.95171(17) -0.0490(3) 0.15459(12) 0.0326(6) Uani 1 1 d D
H2N H 0.944(2) 0.027(3) 0.1763(17) 0.049 Uiso 1 1 d D
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'
S S 0.1246 0.1234 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 Zn1 O1 74.59(10) . 5_755
O1 Zn1 O2 116.18(10) . .
O1 Zn1 O2 105.11(10) 5_755 .
O1 Zn1 N1 138.02(11) . 5_755
O1 Zn1 N1 91.01(10) 5_755 5_755
O2 Zn1 N1 105.56(10) . 5_755
O1 Zn1 N2 89.22(10) . .
O1 Zn1 N2 152.49(11) 5_755 .
O2 Zn1 N2 101.97(10) . .
N1 Zn1 N2 86.37(10) 5_755 .
O1 C1 C6 120.6(3) . .
O1 C1 C2 118.8(3) . .
C6 C1 C2 120.6(3) . .
C3 C2 C1 118.6(3) . .
C3 C2 C10 121.7(3) . .
C1 C2 C10 119.7(3) . .
C4 C3 C2 121.7(3) . .
C4 C3 H3 119.1 . .
C2 C3 H3 119.1 . .
C3 C4 C5 118.7(3) . .
C3 C4 C7 121.3(3) . .
C5 C4 C7 120.0(3) . .
C6 C5 C4 121.1(3) . .
C6 C5 H5 119.5 . .
C4 C5 H5 119.5 . .
C5 C6 C1 119.3(3) . .
C5 C6 C8 120.0(3) . .
C1 C6 C8 120.0(3) . .
C4 C7 H7A 109.5 . .
C4 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C4 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N1 C8 C6 117.7(3) . .
N1 C8 H8A 107.9 . .
C6 C8 H8A 107.9 . .
N1 C8 H8B 107.9 . .
C6 C8 H8B 107.9 . .
H8A C8 H8B 107.2 . .
N1 C9 C11 111.3(3) . 5_755
N1 C9 H9A 109.4 . .
C11 C9 H9A 109.4 5_755 .
N1 C9 H9B 109.4 . .
C11 C9 H9B 109.4 5_755 .
H9A C9 H9B 108.0 . .
N2 C10 C2 112.9(3) . .
N2 C10 H10A 109.0 . .
C2 C10 H10A 109.0 . .
N2 C10 H10B 109.0 . .
C2 C10 H10B 109.0 . .
H10A C10 H10B 107.8 . .
N2 C11 C9 111.5(3) . 5_755
N2 C11 H11A 109.3 . .
C9 C11 H11A 109.3 5_755 .
N2 C11 H11B 109.3 . .
C9 C11 H11B 109.3 5_755 .
H11A C11 H11B 108.0 . .
C13 C12 C16 121.0(3) . 5_765
C13 C12 S1 117.4(2) . .
C16 C12 S1 121.5(2) 5_765 .
C12 C13 C14 120.5(3) . .
C12 C13 H13 119.8 . .
C14 C13 H13 119.8 . .
C15 C14 C13 120.7(3) . .
C15 C14 H14 119.6 . .
C13 C14 H14 119.6 . .
C14 C15 C16 120.6(3) . .
C14 C15 H15 119.7 . .
C16 C15 H15 119.7 . .
C15 C16 C16 119.0(3) . 5_765
C15 C16 C12 122.9(3) . 5_765
C16 C16 C12 118.1(3) 5_765 5_765
C1 O1 Zn1 126.64(19) . .
C1 O1 Zn1 127.3(2) . 5_755
Zn1 O1 Zn1 105.41(10) . 5_755
S1 O2 Zn1 129.06(14) . .
O4 S1 O3 115.44(14) . .
O4 S1 O2 110.25(14) . .
O3 S1 O2 111.97(14) . .
O4 S1 C12 106.40(14) . .
O3 S1 C12 105.90(14) . .
O2 S1 C12 106.20(13) . .
C8 N1 C9 112.1(3) . .
C8 N1 Zn1 115.2(2) . 5_755
C9 N1 Zn1 103.40(19) . 5_755
C8 N1 H1N 106(2) . .
C9 N1 H1N 110(2) . .
Zn1 N1 H1N 111(3) 5_755 .
C11 N2 C10 115.3(3) . .
C11 N2 Zn1 104.34(19) . .
C10 N2 Zn1 112.58(19) . .
C11 N2 H2N 108(3) . .
C10 N2 H2N 111(3) . .
Zn1 N2 H2N 105(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1 1.995(2) .
Zn1 O1 1.995(2) 5_755
Zn1 O2 2.012(2) .
Zn1 N1 2.087(3) 5_755
Zn1 N2 2.121(3) .
C1 O1 1.341(4) .
C1 C6 1.394(4) .
C1 C2 1.403(4) .
C2 C3 1.391(4) .
C2 C10 1.510(5) .
C3 C4 1.384(5) .
C3 H3 0.9300 .
C4 C5 1.398(4) .
C4 C7 1.516(4) .
C5 C6 1.385(4) .
C5 H5 0.9300 .
C6 C8 1.521(4) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 N1 1.482(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 N1 1.482(4) .
C9 C11 1.494(4) 5_755
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 N2 1.487(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 N2 1.481(4) .
C11 C9 1.494(4) 5_755
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.360(4) .
C12 C16 1.429(4) 5_765
C12 S1 1.780(3) .
C13 C14 1.403(5) .
C13 H13 0.9300 .
C14 C15 1.362(4) .
C14 H14 0.9300 .
C15 C16 1.423(4) .
C15 H15 0.9300 .
C16 C16 1.425(6) 5_765
C16 C12 1.429(4) 5_765
O1 Zn1 1.995(2) 5_755
O2 S1 1.478(2) .
O3 S1 1.446(2) .
O4 S1 1.444(2) .
N1 Zn1 2.087(3) 5_755
N1 H1N 0.844(18) .
N2 H2N 0.861(18) .
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_site_symmetry_A
N1 H1N O4 0.844(18) 2.25(2) 3.020(4) 152(3) 3
N2 H2N O3 0.861(18) 2.25(3) 3.008(4) 148(3) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 -178.1(3) . .
C6 C1 C2 C3 -0.7(5) . .
O1 C1 C2 C10 2.7(5) . .
C6 C1 C2 C10 -179.9(3) . .
C1 C2 C3 C4 -0.4(5) . .
C10 C2 C3 C4 178.7(3) . .
C2 C3 C4 C5 0.7(5) . .
C2 C3 C4 C7 -178.1(3) . .
C3 C4 C5 C6 0.1(5) . .
C7 C4 C5 C6 178.9(3) . .
C4 C5 C6 C1 -1.2(5) . .
C4 C5 C6 C8 169.5(3) . .
O1 C1 C6 C5 178.9(3) . .
C2 C1 C6 C5 1.5(5) . .
O1 C1 C6 C8 8.1(5) . .
C2 C1 C6 C8 -169.3(3) . .
C5 C6 C8 N1 135.0(3) . .
C1 C6 C8 N1 -54.3(4) . .
C3 C2 C10 N2 121.6(3) . .
C1 C2 C10 N2 -59.3(4) . .
C16 C12 C13 C14 1.6(5) 5_765 .
S1 C12 C13 C14 -175.2(3) . .
C12 C13 C14 C15 -0.2(5) . .
C13 C14 C15 C16 -1.2(5) . .
C14 C15 C16 C16 1.3(6) . 5_765
C14 C15 C16 C12 -178.7(3) . 5_765
C6 C1 O1 Zn1 -133.0(3) . .
C2 C1 O1 Zn1 44.4(4) . .
C6 C1 O1 Zn1 36.3(4) . 5_755
C2 C1 O1 Zn1 -146.2(2) . 5_755
O1 Zn1 O1 C1 171.2(3) 5_755 .
O2 Zn1 O1 C1 71.7(3) . .
N1 Zn1 O1 C1 -115.0(3) 5_755 .
N2 Zn1 O1 C1 -31.3(3) . .
O1 Zn1 O1 Zn1 0.0 5_755 5_755
O2 Zn1 O1 Zn1 -99.54(12) . 5_755
N1 Zn1 O1 Zn1 73.79(17) 5_755 5_755
N2 Zn1 O1 Zn1 157.49(13) . 5_755
O1 Zn1 O2 S1 -54.46(19) . .
O1 Zn1 O2 S1 -134.44(16) 5_755 .
N1 Zn1 O2 S1 130.17(16) 5_755 .
N2 Zn1 O2 S1 40.63(18) . .
Zn1 O2 S1 O4 -164.90(15) . .
Zn1 O2 S1 O3 -34.9(2) . .
Zn1 O2 S1 C12 80.22(19) . .
C13 C12 S1 O4 114.3(3) . .
C16 C12 S1 O4 -62.5(3) 5_765 .
C13 C12 S1 O3 -9.0(3) . .
C16 C12 S1 O3 174.2(2) 5_765 .
C13 C12 S1 O2 -128.2(3) . .
C16 C12 S1 O2 55.0(3) 5_765 .
C6 C8 N1 C9 167.1(3) . .
C6 C8 N1 Zn1 49.3(3) . 5_755
C11 C9 N1 C8 -168.2(3) 5_755 .
C11 C9 N1 Zn1 -43.5(3) 5_755 5_755
C9 C11 N2 C10 -89.3(3) 5_755 .
C9 C11 N2 Zn1 34.7(3) 5_755 .
C2 C10 N2 C11 -178.6(3) . .
C2 C10 N2 Zn1 61.8(3) . .
O1 Zn1 N2 C11 -146.5(2) . .
O1 Zn1 N2 C11 -93.5(3) 5_755 .
O2 Zn1 N2 C11 96.9(2) . .
N1 Zn1 N2 C11 -8.3(2) 5_755 .
O1 Zn1 N2 C10 -20.8(2) . .
O1 Zn1 N2 C10 32.2(3) 5_755 .
O2 Zn1 N2 C10 -137.4(2) . .
N1 Zn1 N2 C10 117.4(2) 5_755 .
