#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:23:19 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179325 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/22/4322200.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_4322200
loop_
_publ_author_name
'Carla Bazzicalupi'
'Andrea Bencini'
'Antonio Bianchi'
'Claudia Giorgi'
'Vieri Fusi'
'Barbara Valtancoli'
'M. Alexandra Bernardo'
'Fernando Pina'
_publ_section_title
;
 Effect of Protonation and Zn(II) Coordination on the Fluorescence
 Emission of a Phenanthroline-Containing Macrocycle. An Unusual Case of
 "Nonemissive" Zn(II) Complex
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3806
_journal_page_last               3813
_journal_paper_doi               10.1021/ic981374k
_journal_volume                  38
_journal_year                    1999
_chemical_formula_moiety
;
Zn 2+, C18 H21 N5, H2 O, (Cl O4 -)2
;
_chemical_formula_structural
;
(Zn) (C18 H21 N5) (H2 O) (Cl O4)2
;
_chemical_formula_sum            'C18 H23 Cl2 N5 O9 Zn'
_chemical_formula_weight         589.68
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 114.90(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.194(4)
_cell_length_b                   11.959(4)
_cell_length_c                   15.082(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      10.5
_cell_measurement_theta_min      8
_cell_volume                     2322.1(14)
_computing_cell_refinement       'ENRAF NONIUS CAD4'
_computing_data_collection       'ENRAF NONIUS CAD4'
_computing_data_reduction        'ENRAF NONIUS CAD4'
_computing_molecular_graphics    'ORTEP (Johson, 1971)'
_computing_publication_material
;
SHELXL-93 (Sheldrick, 1993), PARST93 (Nardelli, 1993)
;
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SIR92 (Altamore,1993)'
_diffrn_ambient_temperature      298
_diffrn_measurement_device       'ENRAF NONIUS CAD4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0831
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4234
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.72
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.348
_exptl_absorpt_correction_type   'refdelf (Walker and Stuart, 1983)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.023
_refine_ls_goodness_of_fit_obs   1.119
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_restrained_S_obs      1.119
_refine_ls_R_factor_all          0.1552
_refine_ls_R_factor_obs          0.0836
_refine_ls_shift/esd_max         -0.048
_refine_ls_shift/esd_mean        0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1032P)²+8.8527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2468
_refine_ls_wR_factor_obs         0.1961
_reflns_number_observed          2250
_reflns_number_total             4065
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic981374k_2.cif
_cod_data_source_block           '[ZnL(H2O)](ClO4)2'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1032P)^2^+8.8527P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1032P)^2^+8.8527P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4322200
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Zn Zn 0.27750(8) 0.11403(10) 0.18185(8) 0.0577(4) Uani 1 d . .
Cl1 Cl 0.2128(2) 0.0337(2) 0.4588(2) 0.0682(7) Uani 1 d . .
O11 O 0.2206(10) -0.0180(11) 0.3812(9) 0.167(5) Uani 1 d . .
O12 O 0.2900(11) 0.1089(11) 0.5036(11) 0.185(6) Uani 1 d . .
O13 O 0.1287(16) 0.0854(25) 0.4282(19) 0.368(18) Uani 1 d . .
O14 O 0.2016(23) -0.0327(13) 0.5177(13) 0.296(14) Uani 1 d . .
Cl2 Cl 0.3910(2) -0.3699(2) 0.3734(2) 0.0691(7) Uani 1 d . .
O21 O 0.3597(15) -0.4350(12) 0.2920(10) 0.219(8) Uani 1 d . .
O22 O 0.4848(7) -0.3277(13) 0.3934(11) 0.181(6) Uani 1 d . .
O23 O 0.3825(11) -0.4273(11) 0.4505(8) 0.159(5) Uani 1 d . .
O24 O 0.3232(11) -0.2835(13) 0.3572(15) 0.232(9) Uani 1 d . .
O1 O 0.3112(8) 0.1737(8) 0.0722(7) 0.068(2) Uani 1 d . .
HW1 H 0.3652(66) 0.1638(70) 0.0802(57) 0.031(25) Uiso 1 d . .
HW2 H 0.2849(99) 0.2095(115) 0.0407(95) 0.093(58) Uiso 1 d . .
N1 N 0.1243(6) 0.1640(7) 0.1607(5) 0.053(2) Uani 1 d . .
C1 C 0.0921(9) 0.2670(9) 0.1698(7) 0.071(3) Uani 1 d . .
C2 C -0.0079(11) 0.2868(11) 0.1609(8) 0.081(4) Uani 1 d . .
H2 H -0.0271(11) 0.3589(11) 0.1694(8) 0.123(20) Uiso 1 calc R .
C3 C -0.0757(10) 0.2054(13) 0.1407(8) 0.083(4) Uani 1 d . .
H3 H -0.1429(10) 0.2203(13) 0.1332(8) 0.123(20) Uiso 1 calc R .
C4 C -0.0461(7) 0.0935(11) 0.1302(6) 0.065(3) Uani 1 d . .
C5 C 0.0552(7) 0.0796(8) 0.1404(6) 0.052(2) Uani 1 d . .
C6 C 0.0925(6) -0.0297(8) 0.1318(6) 0.050(2) Uani 1 d . .
C7 C 0.0257(8) -0.1210(9) 0.1110(6) 0.061(3) Uani 1 d . .
C8 C -0.0774(8) -0.1039(12) 0.1013(7) 0.077(3) Uani 1 d . .
H8 H -0.1213(8) -0.1651(12) 0.0907(7) 0.123(20) Uiso 1 calc R .
C9 C -0.1127(9) -0.0015(14) 0.1072(8) 0.089(4) Uani 1 d . .
H9 H -0.1818(9) 0.0077(14) 0.0961(8) 0.123(20) Uiso 1 calc R .
C10 C 0.0666(10) -0.2232(10) 0.1040(7) 0.078(3) Uani 1 d . .
H10 H 0.0253(10) -0.2869(10) 0.0919(7) 0.123(20) Uiso 1 calc R .
C11 C 0.1660(11) -0.2328(9) 0.1143(8) 0.080(3) Uani 1 d . .
H11 H 0.1925(11) -0.3020(9) 0.1081(8) 0.123(20) Uiso 1 calc R .
C12 C 0.2287(8) -0.1354(8) 0.1348(7) 0.062(3) Uani 1 d . .
N2 N 0.1916(5) -0.0369(6) 0.1425(5) 0.050(2) Uani 1 d . .
C13 C 0.3371(9) -0.1376(11) 0.1421(9) 0.085(4) Uani 1 d . .
H13A H 0.3731(9) -0.2017(11) 0.1810(9) 0.093(18) Uiso 1 calc R .
H13B H 0.3342(9) -0.1472(11) 0.0772(9) 0.093(18) Uiso 1 calc R .
N3 N 0.3965(6) -0.0372(8) 0.1855(7) 0.074(3) Uani 1 d . .
C14 C 0.4514(19) -0.0499(21) 0.2995(21) 0.082(7) Uiso 0.60 d P .
C15 C 0.4779(13) 0.0630(16) 0.3463(13) 0.069(4) Uiso 0.60 d P .
C14' C 0.4751(27) -0.0459(30) 0.2740(27) 0.082(11) Uiso 0.40 d P .
C15' C 0.4360(26) -0.0257(32) 0.3460(27) 0.095(10) Uiso 0.40 d P .
N4 N 0.3784(7) 0.1121(10) 0.3291(6) 0.089(3) Uani 1 d . .
C16 C 0.4243(30) 0.1928(42) 0.3723(29) 0.098(12) Uiso 0.40 d P .
C16' C 0.4001(18) 0.2479(21) 0.3626(15) 0.070(5) Uiso 0.60 d P .
C17 C 0.3143(14) 0.3042(13) 0.3345(10) 0.111(5) Uani 1 d . .
N5 N 0.2765(10) 0.3152(9) 0.2295(8) 0.095(3) Uani 1 d . .
H5 H 0.3192(10) 0.3582(9) 0.2124(8) 0.110(45) Uiso 1 calc R .
C18 C 0.1708(14) 0.3571(10) 0.1885(10) 0.100(5) Uani 1 d . .
H18A H 0.1570(14) 0.3954(10) 0.1276(10) 0.093(18) Uiso 1 calc R .
H18B H 0.1637(14) 0.4113(10) 0.2332(10) 0.093(18) Uiso 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
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
O1 Zn N4 125.5(4) . . ?
O1 Zn N2 112.1(3) . . ?
N4 Zn N2 110.3(4) . . ?
O1 Zn N1 110.6(4) . . ?
N4 Zn N1 111.2(3) . . ?
N2 Zn N1 76.6(3) . . ?
O1 Zn N3 83.2(4) . . ?
N4 Zn N3 79.0(4) . . ?
N2 Zn N3 71.8(3) . . ?
N1 Zn N3 148.4(3) . . ?
O1 Zn N5 85.9(4) . . ?
N4 Zn N5 77.8(4) . . ?
N2 Zn N5 145.5(3) . . ?
N1 Zn N5 69.4(4) . . ?
N3 Zn N5 141.6(4) . . ?
O13 Cl1 O14 100.9(19) . . ?
O13 Cl1 O12 107.6(15) . . ?
O14 Cl1 O12 112.6(12) . . ?
O13 Cl1 O11 108.4(13) . . ?
O14 Cl1 O11 113.7(10) . . ?
O12 Cl1 O11 112.7(8) . . ?
O22 Cl2 O21 109.6(10) . . ?
O22 Cl2 O24 108.4(9) . . ?
O21 Cl2 O24 109.5(12) . . ?
O22 Cl2 O23 115.2(9) . . ?
O21 Cl2 O23 111.1(8) . . ?
O24 Cl2 O23 102.8(9) . . ?
C1 N1 C5 117.6(8) . . ?
C1 N1 Zn 127.5(7) . . ?
C5 N1 Zn 114.8(6) . . ?
N1 C1 C2 121.6(11) . . ?
N1 C1 C18 115.0(10) . . ?
C2 C1 C18 123.3(12) . . ?
C3 C2 C1 121.1(11) . . ?
C2 C3 C4 119.9(11) . . ?
C5 C4 C9 118.7(11) . . ?
C5 C4 C3 116.0(11) . . ?
C9 C4 C3 125.2(11) . . ?
N1 C5 C4 123.6(9) . . ?
N1 C5 C6 116.2(8) . . ?
C4 C5 C6 120.2(9) . . ?
N2 C6 C7 123.6(9) . . ?
N2 C6 C5 116.9(8) . . ?
C7 C6 C5 119.5(8) . . ?
C10 C7 C6 116.4(10) . . ?
C10 C7 C8 124.6(11) . . ?
C6 C7 C8 118.9(11) . . ?
C9 C8 C7 121.4(11) . . ?
C8 C9 C4 121.2(10) . . ?
C11 C10 C7 121.2(10) . . ?
C10 C11 C12 118.9(10) . . ?
N2 C12 C11 121.1(10) . . ?
N2 C12 C13 116.5(9) . . ?
C11 C12 C13 122.3(10) . . ?
C12 N2 C6 118.9(8) . . ?
C12 N2 Zn 125.7(6) . . ?
C6 N2 Zn 115.3(6) . . ?
N3 C13 C12 113.8(9) . . ?
C14' N3 C13 117.9(18) . . ?
C14' N3 C14 22.5(16) . . ?
C13 N3 C14 109.9(12) . . ?
C14' N3 Zn 110.9(17) . . ?
C13 N3 Zn 109.5(6) . . ?
C14 N3 Zn 96.6(11) . . ?
C14' C14 C15' 151.3(72) . . ?
C14' C14 C15 97.6(53) . . ?
C15' C14 C15 54.3(30) . . ?
C14' C14 N3 56.9(46) . . ?
C15' C14 N3 132.5(37) . . ?
C15 C14 N3 109.9(17) . . ?
C15' C15 N4 85.1(21) . . ?
C15' C15 C14 35.5(18) . . ?
N4 C15 C14 104.4(16) . . ?
C15' C15 C14' 56.4(22) . . ?
N4 C15 C14' 116.2(17) . . ?
C14 C15 C14' 21.0(14) . . ?
C14 C14' N3 100.6(53) . . ?
C14 C14' C15' 16.9(43) . . ?
N3 C14' C15' 108.5(27) . . ?
C14 C14' C15 61.5(47) . . ?
N3 C14' C15 111.6(24) . . ?
C15' C14' C15 44.9(17) . . ?
C14 C15' C15 90.2(38) . . ?
C14 C15' C14' 11.8(30) . . ?
C15 C15' C14' 78.7(25) . . ?
C14 C15' N4 116.3(38) . . ?
C15 C15' N4 52.9(17) . . ?
C14' C15' N4 110.1(24) . . ?
C16 N4 C15 87.9(22) . . ?
C16 N4 C15' 123.3(24) . . ?
C15 N4 C15' 42.0(12) . . ?
C16 N4 C16' 21.7(20) . . ?
C15 N4 C16' 107.2(14) . . ?
C15' N4 C16' 145.0(16) . . ?
C16 N4 Zn 123.3(21) . . ?
C15 N4 Zn 112.2(9) . . ?
C15' N4 Zn 103.2(13) . . ?
C16' N4 Zn 105.4(9) . . ?
C16' C16 N4 121.2(52) . . ?
C16' C16 C17 21.6(31) . . ?
N4 C16 C17 102.0(25) . . ?
C16 C16' C17 146.4(47) . . ?
C16 C16' N4 37.1(38) . . ?
C17 C16' N4 111.9(15) . . ?
C16' C17 N5 105.6(15) . . ?
C16' C17 C16 12.0(17) . . ?
N5 C17 C16 105.3(15) . . ?
C17 N5 C18 109.7(12) . . ?
C17 N5 Zn 100.5(9) . . ?
C18 N5 Zn 109.8(7) . . ?
N5 C18 C1 112.9(10) . . ?
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
Zn O1 2.034(8) . ?
Zn N4 2.075(9) . ?
Zn N2 2.118(7) . ?
Zn N1 2.145(7) . ?
Zn N3 2.460(8) . ?
Zn N5 2.512(10) . ?
Cl1 O13 1.25(2) . ?
Cl1 O14 1.251(12) . ?
Cl1 O12 1.358(11) . ?
Cl1 O11 1.369(10) . ?
Cl2 O22 1.335(10) . ?
Cl2 O21 1.361(12) . ?
Cl2 O24 1.362(12) . ?
Cl2 O23 1.398(11) . ?
N1 C1 1.341(12) . ?
N1 C5 1.351(12) . ?
C1 C2 1.39(2) . ?
C1 C18 1.49(2) . ?
C2 C3 1.31(2) . ?
C3 C4 1.43(2) . ?
C4 C5 1.390(12) . ?
C4 C9 1.42(2) . ?
C5 C6 1.436(13) . ?
C6 N2 1.351(10) . ?
C6 C7 1.392(13) . ?
C7 C10 1.376(15) . ?
C7 C8 1.423(15) . ?
C8 C9 1.34(2) . ?
C10 C11 1.36(2) . ?
C11 C12 1.418(15) . ?
C12 N2 1.315(11) . ?
C12 C13 1.495(15) . ?
C13 N3 1.454(14) . ?
N3 C14' 1.34(3) . ?
N3 C14 1.57(3) . ?
C14 C14' 0.61(4) . ?
C14 C15' 0.87(4) . ?
C14 C15 1.50(3) . ?
C15 C15' 1.21(4) . ?
C15 N4 1.45(2) . ?
C15 C14' 1.69(4) . ?
C14' C15' 1.43(5) . ?
C15' N4 1.81(4) . ?
N4 C16 1.19(4) . ?
N4 C16' 1.69(2) . ?
C16 C16' 0.73(4) . ?
C16 C17 1.95(4) . ?
C16' C17 1.30(2) . ?
C17 N5 1.45(2) . ?
N5 C18 1.45(2) . ?
