#------------------------------------------------------------------------------
#$Date: 2016-03-23 04:09:31 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179278 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/98/4319860.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_4319860
loop_
_publ_author_name
'Carlos Lodeiro'
'A. Jorge Parola'
'Fernando Pina'
'Carla Bazzicalupi'
'Andrea Bencini'
'Antonio Bianchi'
'Claudia Giorgi'
'Andrea Masotti'
'Barbara Valtancoli'
_publ_section_title
;
 Protonation and Zn(II) Coordination by Dipyridine-Containing Macrocycles
 with Different Molecular Architecture. A Case of pH-Controlled Metal
 Jumping Outside-Inside the Macrocyclic Cavity
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2968
_journal_page_last               2975
_journal_paper_doi               10.1021/ic001381k
_journal_volume                  40
_journal_year                    2001
_chemical_formula_moiety
;
C20 H31 N7, Zn, (Cl O4)2
;
_chemical_formula_sum            'C20 H31 Cl2 N7 O8 Zn'
_chemical_formula_weight         633.79
_chemical_name_systematic
;
 ?
;
_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                 94.010(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8480(10)
_cell_length_b                   11.2760(10)
_cell_length_c                   19.688(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      20
_cell_measurement_theta_min      12
_cell_volume                     2623.8(5)
_computing_cell_refinement       'XSCANS, SIEMENS'
_computing_data_collection       'XSCANS, SIEMENS'
_computing_data_reduction        'XSCANS, SIEMENS'
_computing_molecular_graphics    'ORTEP3 Ver. 1.01β (Farrugia, 1997)'
_computing_publication_material  'PARST93 (Nardelli, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1997)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'SIEMENS P4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5406
_diffrn_reflns_theta_full        64.18
_diffrn_reflns_theta_max         64.18
_diffrn_reflns_theta_min         3.74
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.694
_exptl_absorpt_correction_T_max  0.38
_exptl_absorpt_correction_T_min  0.25
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.00079(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         4239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1097P)²+2.2739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1707
_refine_ls_wR_factor_ref         0.1772
_reflns_number_gt                3704
_reflns_number_total             4239
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic001381k_1.cif
_cod_data_source_block           '[ZnL2](ClO4)2'
_cod_database_code               4319860
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_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 0.78710(4) 0.23071(5) 0.09600(3) 0.0514(2) Uani 1 1 d . . .
Cl2 Cl 0.99441(9) 0.19989(9) -0.11906(5) 0.0611(3) Uani 1 1 d . . .
O21 O 1.0965(5) 0.2156(6) -0.1465(5) 0.169(3) Uani 1 1 d . . .
O22 O 0.9165(5) 0.1503(6) -0.1682(3) 0.144(2) Uani 1 1 d . . .
O23 O 0.9452(6) 0.3030(4) -0.0962(3) 0.1313(19) Uani 1 1 d . . .
O24 O 1.0047(4) 0.1140(4) -0.0655(2) 0.1064(14) Uani 1 1 d . . .
Cl3 Cl 1.37094(10) 0.22222(11) -0.30483(7) 0.0745(4) Uani 1 1 d . . .
O31 O 1.4134(13) 0.3247(12) -0.2658(7) 0.137(4) Uani 0.50 1 d P . .
O31' O 1.3696(13) 0.2475(19) -0.2341(7) 0.154(6) Uani 0.50 1 d P . .
O32 O 1.3478(7) 0.2911(6) -0.3612(5) 0.202(4) Uani 1 1 d . . .
O33 O 1.4685(4) 0.1547(5) -0.3113(3) 0.1190(16) Uani 1 1 d . . .
O34 O 1.2809(17) 0.175(2) -0.2747(16) 0.259(16) Uani 0.50 1 d P . .
O34' O 1.2818(9) 0.1359(12) -0.3195(6) 0.102(4) Uani 0.50 1 d P . .
N1 N 0.7032(3) 0.4028(3) 0.06623(17) 0.0549(8) Uani 1 1 d . . .
C1 C 0.7076(4) 0.4957(4) 0.1086(3) 0.0673(11) Uani 1 1 d . . .
C2 C 0.6773(5) 0.6096(4) 0.0846(4) 0.0922(17) Uani 1 1 d . . .
H2 H 0.6799 0.6741 0.1141 0.111 Uiso 1 1 calc R . .
C3 C 0.6443(6) 0.6237(5) 0.0176(4) 0.106(2) Uani 1 1 d . . .
H3 H 0.6232 0.6984 0.0011 0.127 Uiso 1 1 calc R . .
C4 C 0.6418(5) 0.5290(5) -0.0258(3) 0.0928(17) Uani 1 1 d . . .
H4 H 0.6218 0.5392 -0.0720 0.111 Uiso 1 1 calc R . .
C5 C 0.6697(4) 0.4176(4) 0.0000(2) 0.0614(11) Uani 1 1 d . . .
C6 C 0.6668(3) 0.3087(4) -0.0426(2) 0.0573(10) Uani 1 1 d . . .
C7 C 0.6165(5) 0.3069(6) -0.1086(3) 0.0806(15) Uani 1 1 d . . .
H7 H 0.5843 0.3752 -0.1280 0.097 Uiso 1 1 calc R . .
C8 C 0.6152(5) 0.2026(7) -0.1445(3) 0.0888(18) Uani 1 1 d . . .
H8 H 0.5816 0.2000 -0.1886 0.107 Uiso 1 1 calc R . .
C9 C 0.6624(4) 0.1037(6) -0.1161(2) 0.0758(14) Uani 1 1 d . . .
H9 H 0.6636 0.0333 -0.1406 0.091 Uiso 1 1 calc R . .
C10 C 0.7092(3) 0.1092(4) -0.0494(2) 0.0607(11) Uani 1 1 d . . .
N2 N 0.7121(3) 0.2109(3) -0.01297(17) 0.0514(8) Uani 1 1 d . . .
C11 C 0.7582(5) 0.0002(4) -0.0163(3) 0.0793(14) Uani 1 1 d . . .
H11A H 0.7197 -0.0686 -0.0364 0.095 Uiso 1 1 calc R . .
H11B H 0.8373 -0.0054 -0.0255 0.095 Uiso 1 1 calc R . .
N3 N 0.7491(4) -0.0021(4) 0.0561(2) 0.0781(11) Uani 1 1 d . . .
C12 C 0.6333(6) -0.0185(7) 0.0762(3) 0.104(2) Uani 1 1 d . . .
C13 C 0.6196(13) 0.0342(13) 0.1512(8) 0.082(4) Uani 0.40 1 d P . .
C13' C 0.5810(7) 0.0766(8) 0.0999(6) 0.081(3) Uani 0.60 1 d P . .
N4 N 0.6602(4) 0.1548(3) 0.1535(2) 0.0770(12) Uani 1 1 d . . .
C14 C 0.747(2) 0.1418(15) 0.2309(8) 0.072(5) Uani 0.40 1 d P . .
C15 C 0.850(4) 0.066(4) 0.225(3) 0.123(15) Uani 0.40 1 d P . .
C14' C 0.6944(13) 0.1006(17) 0.2101(7) 0.110(5) Uani 0.60 1 d P . .
C15' C 0.824(2) 0.0938(19) 0.2230(12) 0.091(8) Uani 0.60 1 d P . .
N5 N 0.8917(4) 0.1140(4) 0.1621(3) 0.0851(13) Uani 1 1 d . . .
C16 C 1.0055(5) 0.1589(5) 0.1706(4) 0.094(2) Uani 1 1 d . . .
H16A H 1.0568 0.0959 0.1860 0.113 Uiso 1 1 calc R . .
H16B H 1.0099 0.2214 0.2046 0.113 Uiso 1 1 calc R . .
C17 C 1.0382(5) 0.2064(6) 0.1038(4) 0.097(2) Uani 1 1 d . . .
H17A H 1.1090 0.2494 0.1111 0.117 Uiso 1 1 calc R . .
H17B H 1.0508 0.1405 0.0736 0.117 Uiso 1 1 calc R . .
N6 N 0.9516(3) 0.2865(4) 0.0703(2) 0.0715(11) Uani 1 1 d . . .
H6 H 0.9545 0.2777 0.0245 0.086 Uiso 1 1 calc R . .
C18 C 0.9696(5) 0.4132(5) 0.0862(3) 0.0806(14) Uani 1 1 d . . .
H18A H 0.9189 0.4605 0.0564 0.097 Uiso 1 1 calc R . .
H18B H 1.0466 0.4347 0.0777 0.097 Uiso 1 1 calc R . .
C19 C 0.9491(5) 0.4408(5) 0.1593(3) 0.0781(14) Uani 1 1 d . . .
H19A H 1.0124 0.4113 0.1884 0.094 Uiso 1 1 calc R . .
H19B H 0.9463 0.5262 0.1650 0.094 Uiso 1 1 calc R . .
N7 N 0.8440(3) 0.3891(3) 0.18178(18) 0.0634(9) Uani 1 1 d . . .
C20 C 0.7499(5) 0.4721(4) 0.1800(3) 0.0789(14) Uani 1 1 d . . .
H20A H 0.7744 0.5458 0.2017 0.095 Uiso 1 1 calc R . .
H20B H 0.6894 0.4394 0.2049 0.095 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
N4 Zn1 N6 159.03(18) . . ?
N4 Zn1 N5 80.34(19) . . ?
N6 Zn1 N5 80.18(19) . . ?
N4 Zn1 N1 99.82(14) . . ?
N6 Zn1 N1 94.50(16) . . ?
N5 Zn1 N1 154.71(15) . . ?
N4 Zn1 N2 102.64(16) . . ?
N6 Zn1 N2 96.20(13) . . ?
N5 Zn1 N2 132.32(15) . . ?
N1 Zn1 N2 72.63(12) . . ?
N4 Zn1 N7 95.41(15) . . ?
N6 Zn1 N7 75.21(14) . . ?
N5 Zn1 N7 85.01(15) . . ?
N1 Zn1 N7 69.75(12) . . ?
N2 Zn1 N7 140.44(12) . . ?
O21 Cl2 O23 114.9(4) . . ?
O21 Cl2 O22 109.6(5) . . ?
O23 Cl2 O22 106.6(4) . . ?
O21 Cl2 O24 110.3(4) . . ?
O23 Cl2 O24 110.1(3) . . ?
O22 Cl2 O24 104.9(3) . . ?
O32 Cl3 O34 117.2(11) . . ?
O32 Cl3 O33 110.9(5) . . ?
O34 Cl3 O33 120.0(9) . . ?
O32 Cl3 O31' 131.7(9) . . ?
O34 Cl3 O31' 65.9(14) . . ?
O33 Cl3 O31' 105.3(6) . . ?
O32 Cl3 O34' 96.8(6) . . ?
O34 Cl3 O34' 40.8(15) . . ?
O33 Cl3 O34' 102.2(6) . . ?
O31' Cl3 O34' 105.8(9) . . ?
O32 Cl3 O31 91.1(7) . . ?
O34 Cl3 O31 109.6(15) . . ?
O33 Cl3 O31 102.9(6) . . ?
O31' Cl3 O31 49.6(8) . . ?
O34' Cl3 O31 149.0(8) . . ?
O31' O31 Cl3 63.7(9) . . ?
O31 O31' Cl3 66.7(10) . . ?
O31 O31' O34 115.1(16) . . ?
Cl3 O31' O34 55.2(8) . . ?
O34' O34 Cl3 74.3(13) . . ?
O34' O34 O31' 131.5(18) . . ?
Cl3 O34 O31' 58.8(10) . . ?
O34 O34' Cl3 65.0(14) . . ?
C1 N1 C5 120.1(4) . . ?
C1 N1 Zn1 121.2(3) . . ?
C5 N1 Zn1 117.2(3) . . ?
N1 C1 C2 120.6(5) . . ?
N1 C1 C20 116.5(4) . . ?
C2 C1 C20 122.9(5) . . ?
C3 C2 C1 118.8(5) . . ?
C2 C3 C4 120.5(5) . . ?
C3 C4 C5 119.0(5) . . ?
N1 C5 C4 121.0(5) . . ?
N1 C5 C6 115.9(4) . . ?
C4 C5 C6 123.1(4) . . ?
N2 C6 C7 121.8(5) . . ?
N2 C6 C5 116.2(4) . . ?
C7 C6 C5 122.0(4) . . ?
C8 C7 C6 118.8(5) . . ?
C9 C8 C7 120.3(5) . . ?
C8 C9 C10 118.7(5) . . ?
N2 C10 C9 122.1(5) . . ?
N2 C10 C11 118.3(4) . . ?
C9 C10 C11 119.6(4) . . ?
C6 N2 C10 118.2(4) . . ?
C6 N2 Zn1 116.6(3) . . ?
C10 N2 Zn1 125.3(3) . . ?
N3 C11 C10 113.2(4) . . ?
C11 N3 C12 113.9(4) . . ?
C13' C12 N3 117.2(6) . . ?
C13' C12 C13 46.0(7) . . ?
N3 C12 C13 110.9(6) . . ?
C13' C13 N4 75.7(10) . . ?
C13' C13 C14' 126.4(12) . . ?
N4 C13 C14' 50.8(7) . . ?
C13' C13 C12 54.8(8) . . ?
N4 C13 C12 108.8(10) . . ?
C14' C13 C12 138.9(11) . . ?
C13 C13' C12 79.2(10) . . ?
C13 C13' N4 59.5(8) . . ?
C12 C13' N4 113.7(7) . . ?
C14' N4 C13 70.6(12) . . ?
C14' N4 C13' 115.4(11) . . ?
C13 N4 C13' 44.8(6) . . ?
C14' N4 C14 27.0(10) . . ?
C13 N4 C14 96.9(9) . . ?
C13' N4 C14 141.5(7) . . ?
C14' N4 Zn1 116.9(7) . . ?
C13 N4 Zn1 127.6(7) . . ?
C13' N4 Zn1 105.7(4) . . ?
C14 N4 Zn1 95.9(7) . . ?
C14' C14 C15' 105(3) . . ?
C14' C14 C15 103(3) . . ?
C15' C14 C15 6(3) . . ?
C14' C14 N4 44.1(15) . . ?
C15' C14 N4 111.0(16) . . ?
C15 C14 N4 114(3) . . ?
N5 C15 C14 100(2) . . ?
N5 C15 C14' 100(2) . . ?
C14 C15 C14' 26.2(11) . . ?
C14 C14' N4 109(2) . . ?
C14 C14' C15' 43.0(19) . . ?
N4 C14' C15' 114.1(12) . . ?
C14 C14' C13 162(2) . . ?
N4 C14' C13 58.6(9) . . ?
C15' C14' C13 126.3(15) . . ?
C14 C14' C15 51(2) . . ?
N4 C14' C15 118.1(19) . . ?
C15' C14' C15 8.9(19) . . ?
C13 C14' C15 120(2) . . ?
C14 C15' N5 122.7(16) . . ?
C14 C15' C14' 32.4(11) . . ?
N5 C15' C14' 116.1(13) . . ?
C16 N5 C15 113.2(19) . . ?
C16 N5 C15' 120.4(9) . . ?
C15 N5 C15' 17(2) . . ?
C16 N5 Zn1 110.3(4) . . ?
C15 N5 Zn1 121.2(16) . . ?
C15' N5 Zn1 104.9(10) . . ?
N5 C16 C17 108.8(4) . . ?
N6 C17 C16 113.2(5) . . ?
C18 N6 C17 114.1(4) . . ?
C18 N6 Zn1 110.8(3) . . ?
C17 N6 Zn1 109.2(4) . . ?
N6 C18 C19 111.8(4) . . ?
N7 C19 C18 113.7(4) . . ?
C20 N7 C19 113.7(4) . . ?
C20 N7 Zn1 105.8(3) . . ?
C19 N7 Zn1 105.8(3) . . ?
N7 C20 C1 110.3(4) . . ?
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 N4 2.125(4) . ?
Zn1 N6 2.141(4) . ?
Zn1 N5 2.176(4) . ?
Zn1 N1 2.239(3) . ?
Zn1 N2 2.275(3) . ?
Zn1 N7 2.517(3) . ?
Cl2 O21 1.371(5) . ?
Cl2 O23 1.389(5) . ?
Cl2 O22 1.406(5) . ?
Cl2 O24 1.431(4) . ?
Cl3 O32 1.366(6) . ?
Cl3 O34 1.366(15) . ?
Cl3 O33 1.397(4) . ?
Cl3 O31' 1.423(12) . ?
Cl3 O34' 1.451(10) . ?
Cl3 O31 1.457(13) . ?
O31 O31' 1.21(2) . ?
O31' O34 1.52(3) . ?
O34 O34' 0.98(3) . ?
N1 C1 1.338(6) . ?
N1 C5 1.346(5) . ?
C1 C2 1.405(7) . ?
C1 C20 1.483(7) . ?
C2 C3 1.360(9) . ?
C3 C4 1.366(9) . ?
C4 C5 1.387(7) . ?
C5 C6 1.487(6) . ?
C6 N2 1.342(6) . ?
C6 C7 1.391(7) . ?
C7 C8 1.371(8) . ?
C8 C9 1.352(8) . ?
C9 C10 1.390(7) . ?
C10 N2 1.352(5) . ?
C10 C11 1.489(7) . ?
C11 N3 1.438(7) . ?
N3 C12 1.465(8) . ?
C12 C13' 1.339(11) . ?
C12 C13 1.611(16) . ?
C13 C13' 1.180(16) . ?
C13 N4 1.442(13) . ?
C13 C14' 1.60(2) . ?
C13' N4 1.622(11) . ?
N4 C14' 1.310(13) . ?
N4 C14 1.78(2) . ?
C14 C14' 0.856(18) . ?
C14 C15' 1.09(3) . ?
C14 C15 1.50(5) . ?
C15 N5 1.47(6) . ?
C15 C14' 1.89(5) . ?
C14' C15' 1.55(3) . ?
C15' N5 1.50(3) . ?
N5 C16 1.439(7) . ?
C16 C17 1.497(10) . ?
C17 N6 1.486(8) . ?
N6 C18 1.475(7) . ?
C18 C19 1.509(7) . ?
C19 N7 1.471(6) . ?
N7 C20 1.454(6) . ?
