#------------------------------------------------------------------------------
#$Date: 2016-03-23 14:49:44 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179308 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/05/4320583.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_4320583
loop_
_publ_author_name
'Paolo Dapporto'
'Mauro Formica'
'Vieri Fusi'
'Luca Giorgi'
'Mauro Micheloni'
'Paola Paoli'
'Roberto Pontellini'
'Patrizia Rossi'
_publ_contact_author
;
    Prof. Vieri Fusi
    Institute of Chemical Sciences
    Univeristy of Urbino
    P.zza Rinascimento 6
    I-61029 Urbino ITALY
;
_publ_contact_author_email       vieri@chim.uniurb.it
_publ_section_title
;
 Addition of Small Molecules by Zn(II) and Cu(II) Dinuclear Complexes
 Obtained by an Amino-Phenolic Ligand. Crystal Structures of the Dinuclear
 Zinc Complex Assembling Butanolate and Azide Anions
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6186
_journal_page_last               6192
_journal_paper_doi               10.1021/ic0105415
_journal_volume                  40
_journal_year                    2001
_chemical_formula_moiety
'C16 H31 N6 O 1-,(Zn 2+)2,C4 H9 O 1-,(Cl O4 1-)2'
_chemical_formula_sum            'C20 H40 Cl2 N6 O10 Zn2'
_chemical_formula_weight         726.22
_chemical_name_systematic
;
   ?
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P -2bc 2a'
_symmetry_space_group_name_H-M   'P 21 n b'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   11.483(5)
_cell_length_b                   14.166(5)
_cell_length_c                   18.279(5)
_cell_measurement_temperature    200
_cell_volume                     2973.4(19)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP (Johnson, 1971)'
_computing_publication_material  'PARST97 (Nardelli,1983)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Siemens/SMART CCD'
_diffrn_radiation_monochromator  'Gobel mirrors'
_diffrn_radiation_source         'Siemens Cu rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7961
_diffrn_reflns_theta_full        56.37
_diffrn_reflns_theta_max         56.37
_diffrn_reflns_theta_min         3.95
_exptl_absorpt_coefficient_mu    4.165
_exptl_absorpt_correction_type   'SADABS, SHELDRICK'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.30
_refine_diff_density_max         1.526
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.145
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.40(4)
_refine_ls_extinction_coef       0.00008(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0617
_refine_ls_shift/su_max          0.119
_refine_ls_shift/su_mean         0.014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1379P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1528
_refine_ls_wR_factor_ref         0.1611
_reflns_number_gt                2593
_reflns_number_total             2957
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0105415_1.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'orthorombic' was replaced with
'orthorhombic' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4320583
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, -z'
'x+1/2, -y+1/2, z+1/2'
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn -0.06122(11) 0.16019(9) 0.90433(6) 0.0338(4) Uani 1 1 d . . .
Zn2 Zn 0.13763(12) 0.30668(9) 0.90668(6) 0.0344(4) Uani 1 1 d . . .
Cl1 Cl 0.3304(2) 0.03708(19) 0.90197(14) 0.0464(7) Uani 1 1 d . . .
Cl2 Cl -0.2608(3) 0.45444(19) 0.92994(18) 0.0578(8) Uani 1 1 d . . .
O1 O 0.0270(6) 0.2425(4) 0.8320(3) 0.0278(14) Uani 1 1 d . . .
O2 O 0.2644(11) -0.0391(7) 0.9258(8) 0.127(5) Uani 1 1 d . . .
O3 O 0.4162(11) 0.0026(11) 0.8533(6) 0.131(5) Uani 1 1 d . . .
O4 O 0.3912(9) 0.0829(6) 0.9607(4) 0.076(3) Uani 1 1 d . . .
O5 O 0.2561(8) 0.1008(5) 0.8655(4) 0.060(2) Uani 1 1 d . . .
O6 O -0.1936(9) 0.3989(7) 0.8798(5) 0.085(3) Uani 1 1 d . . .
O7 O -0.3257(16) 0.3989(9) 0.9757(7) 0.182(8) Uani 1 1 d . . .
O8 O -0.1885(13) 0.5191(9) 0.9644(9) 0.169(8) Uani 1 1 d . . .
O9 O -0.333(3) 0.510(2) 0.8944(19) 0.339(19) Uani 1 1 d . . .
O10 O 0.0509(7) 0.2204(5) 0.9718(3) 0.0453(18) Uani 1 1 d . . .
N1 N -0.1795(7) 0.1146(5) 0.8185(4) 0.0309(18) Uani 1 1 d . . .
N2 N -0.0117(8) 0.0184(7) 0.9011(5) 0.050(3) Uani 1 1 d . . .
H1N2 H 0.0623 0.0141 0.8853 0.058(5) Uiso 1 1 calc R . .
H2N2 H -0.0150 -0.0060 0.9465 0.058(5) Uiso 1 1 calc R . .
N3 N -0.2167(8) 0.1882(6) 0.9588(4) 0.043(2) Uani 1 1 d . . .
H1N3 H -0.2246 0.1479 0.9966 0.058(5) Uiso 1 1 calc R . .
H2N3 H -0.2148 0.2472 0.9770 0.058(5) Uiso 1 1 calc R . .
N4 N 0.2323(7) 0.3658(5) 0.8134(4) 0.0297(17) Uani 1 1 d . . .
N5 N 0.3060(8) 0.2965(5) 0.9509(5) 0.041(2) Uani 1 1 d . . .
H1N5 H 0.3152 0.3399 0.9864 0.058(5) Uiso 1 1 calc R . .
H2N5 H 0.3163 0.2389 0.9707 0.058(5) Uiso 1 1 calc R . .
N6 N 0.0663(9) 0.4410(7) 0.9118(5) 0.054(3) Uani 1 1 d . . .
H1N6 H -0.0097 0.4386 0.9000 0.058(5) Uiso 1 1 calc R . .
H2N6 H 0.0724 0.4636 0.9577 0.058(5) Uiso 1 1 calc R . .
C1 C 0.0258(8) 0.2406(6) 0.7583(5) 0.027(2) Uani 1 1 d . . .
C2 C -0.0760(8) 0.2117(6) 0.7205(5) 0.029(2) Uani 1 1 d . . .
C3 C -0.0773(9) 0.2087(6) 0.6444(5) 0.033(2) Uani 1 1 d . . .
H3 H -0.1434 0.1877 0.6200 0.058(5) Uiso 1 1 calc R . .
C4 C 0.0189(10) 0.2365(7) 0.6054(5) 0.039(3) Uani 1 1 d . . .
H4 H 0.0170 0.2357 0.5545 0.058(5) Uiso 1 1 calc R . .
C5 C 0.1177(9) 0.2657(6) 0.6409(5) 0.038(3) Uani 1 1 d . . .
H5 H 0.1824 0.2835 0.6136 0.058(5) Uiso 1 1 calc R . .
C6 C 0.1234(8) 0.2693(5) 0.7182(5) 0.026(2) Uani 1 1 d . . .
C7 C -0.1886(9) 0.1883(7) 0.7604(5) 0.037(2) Uani 1 1 d . . .
H7A H -0.2182 0.2458 0.7825 0.058(5) Uiso 1 1 calc R . .
H7B H -0.2455 0.1676 0.7246 0.058(5) Uiso 1 1 calc R . .
C8 C -0.1311(10) 0.0253(6) 0.7916(5) 0.042(3) Uani 1 1 d . . .
H8A H -0.0678 0.0386 0.7581 0.058(5) Uiso 1 1 calc R . .
H8B H -0.1908 -0.0086 0.7648 0.058(5) Uiso 1 1 calc R . .
C9 C -0.0870(9) -0.0357(7) 0.8529(6) 0.046(3) Uani 1 1 d . . .
H9A H -0.1523 -0.0605 0.8805 0.058(5) Uiso 1 1 calc R . .
H9B H -0.0440 -0.0887 0.8328 0.058(5) Uiso 1 1 calc R . .
C10 C -0.2931(9) 0.0981(7) 0.8541(6) 0.042(3) Uani 1 1 d . . .
H10A H -0.2921 0.0379 0.8794 0.058(5) Uiso 1 1 calc R . .
H10B H -0.3542 0.0963 0.8175 0.058(5) Uiso 1 1 calc R . .
C11 C -0.3177(11) 0.1786(9) 0.9094(6) 0.050(3) Uani 1 1 d . . .
H11A H -0.3306 0.2374 0.8834 0.058(5) Uiso 1 1 calc R . .
H11B H -0.3871 0.1642 0.9375 0.058(5) Uiso 1 1 calc R . .
C12 C 0.2389(9) 0.2951(6) 0.7529(5) 0.035(2) Uani 1 1 d . . .
H12A H 0.2745 0.2380 0.7717 0.058(5) Uiso 1 1 calc R . .
H12B H 0.2897 0.3199 0.7151 0.058(5) Uiso 1 1 calc R . .
C13 C 0.3481(9) 0.3889(7) 0.8392(6) 0.045(3) Uani 1 1 d . . .
H13A H 0.3463 0.4492 0.8643 0.058(5) Uiso 1 1 calc R . .
H13B H 0.4003 0.3946 0.7977 0.058(5) Uiso 1 1 calc R . .
C14 C 0.3944(11) 0.3124(8) 0.8916(6) 0.044(3) Uani 1 1 d . . .
H14A H 0.4078 0.2542 0.8651 0.058(5) Uiso 1 1 calc R . .
H14B H 0.4676 0.3327 0.9130 0.058(5) Uiso 1 1 calc R . .
C15 C 0.1677(10) 0.4509(6) 0.7932(5) 0.040(3) Uani 1 1 d . . .
H15A H 0.1002 0.4334 0.7643 0.058(5) Uiso 1 1 calc R . .
H15B H 0.2168 0.4912 0.7635 0.058(5) Uiso 1 1 calc R . .
C16 C 0.1284(11) 0.5045(7) 0.8605(6) 0.047(3) Uani 1 1 d . . .
H16A H 0.1956 0.5318 0.8848 0.058(5) Uiso 1 1 calc R . .
H16B H 0.0771 0.5557 0.8460 0.058(5) Uiso 1 1 calc R . .
C17 C 0.0880(11) 0.1786(8) 1.0371(6) 0.053(3) Uani 1 1 d . . .
H17A H 0.1667 0.1552 1.0305 0.058(5) Uiso 1 1 calc R . .
H17B H 0.0383 0.1250 1.0477 0.058(5) Uiso 1 1 calc R . .
C18 C 0.0861(13) 0.2466(11) 1.1032(7) 0.073(4) Uani 1 1 d . . .
H18A H 0.1077 0.2124 1.1471 0.058(5) Uiso 1 1 calc R . .
H18B H 0.1428 0.2964 1.0957 0.058(5) Uiso 1 1 calc R . .
C19 C -0.0295(13) 0.2883(12) 1.1129(7) 0.076(4) Uani 1 1 d . . .
H19A H -0.0873 0.2386 1.1170 0.058(5) Uiso 1 1 calc R . .
H19B H -0.0488 0.3267 1.0707 0.058(5) Uiso 1 1 calc R . .
C20 C -0.0307(15) 0.3487(10) 1.1816(8) 0.083(5) Uani 1 1 d . . .
H20A H -0.0080 0.3110 1.2228 0.058(5) Uiso 1 1 calc R . .
H20B H -0.1077 0.3731 1.1894 0.058(5) Uiso 1 1 calc R . .
H20C H 0.0229 0.4002 1.1759 0.058(5) Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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
_geom_angle_publ_flag
O10 Zn1 O1 80.4(3) . . ?
O10 Zn1 N3 100.2(3) . . ?
O1 Zn1 N3 129.0(3) . . ?
O10 Zn1 N2 104.8(3) . . ?
O1 Zn1 N2 113.4(3) . . ?
N3 Zn1 N2 115.5(3) . . ?
O10 Zn1 N1 170.4(3) . . ?
O1 Zn1 N1 90.7(3) . . ?
N3 Zn1 N1 82.3(3) . . ?
N2 Zn1 N1 82.2(3) . . ?
O10 Zn1 Zn2 38.65(18) . . ?
O1 Zn1 Zn2 41.83(16) . . ?
N3 Zn1 Zn2 120.0(2) . . ?
N2 Zn1 Zn2 116.5(3) . . ?
N1 Zn1 Zn2 132.3(2) . . ?
O10 Zn2 O1 79.4(3) . . ?
O10 Zn2 N6 110.0(4) . . ?
O1 Zn2 N6 101.0(3) . . ?
O10 Zn2 N5 100.9(3) . . ?
O1 Zn2 N5 141.9(3) . . ?
N6 Zn2 N5 114.1(4) . . ?
O10 Zn2 N4 163.0(3) . . ?
O1 Zn2 N4 87.7(2) . . ?
N6 Zn2 N4 83.1(3) . . ?
N5 Zn2 N4 82.4(3) . . ?
O10 Zn2 Zn1 38.67(19) . . ?
O1 Zn2 Zn1 40.80(16) . . ?
N6 Zn2 Zn1 109.0(3) . . ?
N5 Zn2 Zn1 129.8(2) . . ?
N4 Zn2 Zn1 127.87(19) . . ?
O2 Cl1 O3 108.0(9) . . ?
O2 Cl1 O5 108.4(6) . . ?
O3 Cl1 O5 110.2(6) . . ?
O2 Cl1 O4 112.5(7) . . ?
O3 Cl1 O4 106.7(7) . . ?
O5 Cl1 O4 111.0(5) . . ?
O9 Cl2 O7 107.5(17) . . ?
O9 Cl2 O8 101.9(17) . . ?
O7 Cl2 O8 115.3(9) . . ?
O9 Cl2 O6 110.7(17) . . ?
O7 Cl2 O6 111.6(6) . . ?
O8 Cl2 O6 109.3(7) . . ?
C1 O1 Zn1 129.3(5) . . ?
C1 O1 Zn2 132.3(6) . . ?
Zn1 O1 Zn2 97.4(2) . . ?
C17 O10 Zn2 128.5(7) . . ?
C17 O10 Zn1 123.3(6) . . ?
Zn2 O10 Zn1 102.7(3) . . ?
C8 N1 C10 110.3(8) . . ?
C8 N1 C7 113.1(7) . . ?
C10 N1 C7 111.2(7) . . ?
C8 N1 Zn1 105.2(6) . . ?
C10 N1 Zn1 106.3(6) . . ?
C7 N1 Zn1 110.4(6) . . ?
C9 N2 Zn1 111.3(6) . . ?
C11 N3 Zn1 111.3(6) . . ?
C13 N4 C15 111.2(7) . . ?
C13 N4 C12 110.2(8) . . ?
C15 N4 C12 113.0(7) . . ?
C13 N4 Zn2 106.8(6) . . ?
C15 N4 Zn2 105.1(6) . . ?
C12 N4 Zn2 110.3(5) . . ?
C14 N5 Zn2 109.6(6) . . ?
C16 N6 Zn2 109.8(7) . . ?
O1 C1 C6 120.6(8) . . ?
O1 C1 C2 120.1(8) . . ?
C6 C1 C2 119.3(8) . . ?
C3 C2 C1 120.3(9) . . ?
C3 C2 C7 117.6(8) . . ?
C1 C2 C7 122.0(8) . . ?
C4 C3 C2 120.1(9) . . ?
C5 C4 C3 120.4(9) . . ?
C4 C5 C6 121.5(9) . . ?
C1 C6 C5 118.3(9) . . ?
C1 C6 C12 123.6(8) . . ?
C5 C6 C12 117.8(8) . . ?
N1 C7 C2 115.7(8) . . ?
N1 C8 C9 112.0(8) . . ?
N2 C9 C8 110.4(8) . . ?
N1 C10 C11 109.5(9) . . ?
N3 C11 C10 108.9(9) . . ?
N4 C12 C6 115.3(8) . . ?
N4 C13 C14 111.1(9) . . ?
N5 C14 C13 108.8(9) . . ?
N4 C15 C16 111.1(7) . . ?
N6 C16 C15 110.6(8) . . ?
O10 C17 C18 113.6(10) . . ?
C19 C18 C17 111.0(11) . . ?
C18 C19 C20 109.6(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O10 1.976(7) . ?
Zn1 O1 2.033(6) . ?
Zn1 N3 2.083(9) . ?
Zn1 N2 2.088(10) . ?
Zn1 N1 2.174(7) . ?
Zn1 Zn2 3.0858(19) . ?
Zn2 O10 1.975(7) . ?
Zn2 O1 2.075(6) . ?
Zn2 N6 2.074(10) . ?
Zn2 N5 2.100(8) . ?
Zn2 N4 2.188(8) . ?
Cl1 O2 1.389(10) . ?
Cl1 O3 1.415(11) . ?
Cl1 O5 1.410(7) . ?
Cl1 O4 1.435(8) . ?
Cl2 O9 1.32(2) . ?
Cl2 O7 1.369(11) . ?
Cl2 O8 1.387(12) . ?
Cl2 O6 1.434(9) . ?
O1 C1 1.348(10) . ?
O10 C17 1.399(12) . ?
N1 C8 1.465(11) . ?
N1 C10 1.477(12) . ?
N1 C7 1.494(12) . ?
N2 C9 1.453(14) . ?
N3 C11 1.476(14) . ?
N4 C13 1.449(13) . ?
N4 C15 1.463(12) . ?
N4 C12 1.494(11) . ?
N5 C14 1.501(14) . ?
N6 C16 1.482(15) . ?
C1 C6 1.399(13) . ?
C1 C2 1.417(13) . ?
C2 C3 1.391(12) . ?
C2 C7 1.521(13) . ?
C3 C4 1.373(15) . ?
C4 C5 1.371(15) . ?
C5 C6 1.416(13) . ?
C6 C12 1.515(14) . ?
C8 C9 1.503(14) . ?
C10 C11 1.548(14) . ?
C13 C14 1.541(14) . ?
C15 C16 1.514(14) . ?
C17 C18 1.545(16) . ?
C18 C19 1.464(19) . ?
C19 C20 1.519(19) . ?
