#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:56:45 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179136 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/98/4309870.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_4309870
loop_
_publ_author_name
'Abel Tamayo'
'Carlos Lodeiro'
'Lluis Escriche'
'Jaume Casabó'
'Berta Covelo'
'Pablo González'
_publ_contact_author_address
; REQUIMTE-CQTB
  Departamento de Química
  Faculdade de Ciências e Tecnologia
  Universidade Nova de Lisboa
  2829-516 Monte de Caparica
  Portugal
;
_publ_contact_author_email
;       
'lodeiro@dq.fct.unl.pt (CL) & lluis.escriche@uab.es (LE)'
;
_publ_contact_author_fax
;
'00 351 21 2948385 (CL) & 00 34 93 5812497 (LE)'
;
_publ_contact_author_name        'Dr. Carlos Lodeiro & Dr. Lluis Escriche'
_publ_contact_author_phone       '00 351 21 2948300 (CL)'
_publ_section_title
;
New Fluorescence PET Systems Based on N2S2 Pyridine-Anthracene-Containing
Macrocyclic Ligands. Spectrophotometric, Spectrofluorimetric, and Metal Ion
Binding Studies
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8105
_journal_page_last               8115
_journal_paper_doi               10.1021/ic050926d
_journal_volume                  44
_journal_year                    2005
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C28 H30 Cl1 Cu1 N2 O4 S2, Cl O4'
_chemical_formula_sum            'C28 H30 Cl2 Cu N2 O8 S2'
_chemical_formula_weight         721.10
_chemical_name_systematic
;
 7-(9-anthracenylmethyl)-3,11-dithia-7,17-
 diazabicyclo[11.3.1]heptadeca-1(17),13,15-triene-?4S,N,S',N'-
 perchloratocopper(II) perchlorate
;
_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                 95.403(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.901(3)
_cell_length_b                   9.145(3)
_cell_length_c                   35.075(10)
_cell_measurement_temperature    293(2)
_cell_volume                     2842.4(16)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF ( Beurskens et al., 1996)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_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  0.0748
_diffrn_reflns_av_sigmaI/netI    0.0739
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            23500
_diffrn_reflns_theta_full        26.46
_diffrn_reflns_theta_max         26.46
_diffrn_reflns_theta_min         1.17
_exptl_absorpt_coefficient_mu    1.160
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1484
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.813
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0485
_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)+(0.0589P)²+5.6273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1421
_reflns_number_gt                3741
_reflns_number_total             5843
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic050926drom20050608_021110_1.cif
_cod_data_source_block           culan
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4309870
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
Cu Cu 0.25445(6) 0.18920(6) 0.351348(16) 0.01626(16) Uani 1 1 d . A .
C1 C 0.1437(5) 0.1384(5) 0.42688(13) 0.0191(10) Uani 1 1 d . . .
H1 H 0.1462 0.0571 0.4110 0.023 Uiso 1 1 calc R . .
C2 C 0.0126(5) 0.2137(5) 0.42803(14) 0.0222(11) Uani 1 1 d . . .
H2 H -0.0729 0.1832 0.4128 0.027 Uiso 1 1 calc R . .
C3 C 0.0036(5) 0.3370(6) 0.45173(15) 0.0269(12) Uani 1 1 d . . .
H3 H -0.0842 0.3926 0.4505 0.032 Uiso 1 1 calc R . .
C4 C 0.1243(5) 0.3741(6) 0.47646(14) 0.0236(11) Uani 1 1 d . . .
H4 H 0.1160 0.4514 0.4934 0.028 Uiso 1 1 calc R . .
C5 C 0.2627(5) 0.2969(5) 0.47695(13) 0.0165(10) Uani 1 1 d . . .
C6 C 0.2779(5) 0.1824(5) 0.44969(13) 0.0167(10) Uani 1 1 d . . .
C7 C 0.4210(5) 0.1185(5) 0.44599(13) 0.0153(10) Uani 1 1 d . . .
C8 C 0.5432(5) 0.1505(5) 0.47393(13) 0.0165(10) Uani 1 1 d . . .
C9 C 0.5223(5) 0.2568(5) 0.50290(13) 0.0195(10) Uani 1 1 d . . .
C10 C 0.3856(5) 0.3305(5) 0.50303(13) 0.0190(10) Uani 1 1 d . . .
H10 H 0.3760 0.4039 0.5210 0.023 Uiso 1 1 calc R . .
C11 C 0.6464(6) 0.2911(6) 0.53053(14) 0.0249(11) Uani 1 1 d . . .
H11 H 0.6343 0.3613 0.5492 0.030 Uiso 1 1 calc R . .
C12 C 0.7817(6) 0.2222(6) 0.52986(15) 0.0280(12) Uani 1 1 d . . .
H12 H 0.8610 0.2444 0.5481 0.034 Uiso 1 1 calc R . .
C13 C 0.8006(5) 0.1177(6) 0.50154(15) 0.0277(12) Uani 1 1 d . . .
H13 H 0.8934 0.0711 0.5014 0.033 Uiso 1 1 calc R . .
C14 C 0.6882(5) 0.0823(5) 0.47433(14) 0.0212(11) Uani 1 1 d . . .
H14 H 0.7053 0.0132 0.4558 0.025 Uiso 1 1 calc R . .
C15 C 0.4417(5) 0.0243(5) 0.41212(12) 0.0178(10) Uani 1 1 d . . .
H15A H 0.3561 -0.0414 0.4081 0.021 Uiso 1 1 calc R . .
H15B H 0.5313 -0.0352 0.4178 0.021 Uiso 1 1 calc R . .
N16 N 0.4572(4) 0.1079(4) 0.37536(11) 0.0170(8) Uani 1 1 d . . .
C17 C 0.5176(6) 0.0026(5) 0.34703(14) 0.0228(11) Uani 1 1 d . . .
H17A H 0.5244 0.0555 0.3233 0.027 Uiso 1 1 calc R . .
H17B H 0.6197 -0.0232 0.3568 0.027 Uiso 1 1 calc R . .
C18 C 0.4335(6) -0.1381(5) 0.33732(14) 0.0250(12) Uani 1 1 d . . .
H18A H 0.4056 -0.1818 0.3608 0.030 Uiso 1 1 calc R . .
H18B H 0.5009 -0.2055 0.3260 0.030 Uiso 1 1 calc R . .
C19 C 0.2923(6) -0.1198(5) 0.31000(14) 0.0241(11) Uani 1 1 d . . .
H19A H 0.2584 -0.2137 0.2996 0.029 Uiso 1 1 calc R . .
H19B H 0.3116 -0.0556 0.2890 0.029 Uiso 1 1 calc R . .
S20 S 0.15135(14) -0.04056(13) 0.33807(3) 0.0196(3) Uani 1 1 d . . .
C21 C -0.0020(6) 0.0133(6) 0.30338(14) 0.0246(11) Uani 1 1 d . . .
H21A H 0.0275 -0.0034 0.2778 0.030 Uiso 1 1 calc R . .
H21B H -0.0892 -0.0475 0.3066 0.030 Uiso 1 1 calc R . .
C22 C -0.0447(5) 0.1704(5) 0.30719(12) 0.0183(10) Uani 1 1 d . . .
C23 C -0.1836(6) 0.2208(6) 0.29188(13) 0.0226(11) Uani 1 1 d . . .
H23 H -0.2542 0.1565 0.2801 0.027 Uiso 1 1 calc R . .
C24 C -0.2163(6) 0.3670(6) 0.29428(14) 0.0256(12) Uani 1 1 d . . .
H24 H -0.3107 0.4019 0.2848 0.031 Uiso 1 1 calc R . .
C25 C -0.1089(5) 0.4617(6) 0.31069(14) 0.0243(11) Uani 1 1 d . . .
H25 H -0.1293 0.5612 0.3122 0.029 Uiso 1 1 calc R . .
C26 C 0.0289(5) 0.4073(5) 0.32483(13) 0.0195(10) Uani 1 1 d . . .
N27 N 0.0603(4) 0.2631(4) 0.32433(11) 0.0181(9) Uani 1 1 d . . .
C28 C 0.1564(6) 0.5058(5) 0.34016(14) 0.0236(11) Uani 1 1 d . . .
H28A H 0.1160 0.5974 0.3486 0.028 Uiso 1 1 calc R . .
H28B H 0.2209 0.5270 0.3201 0.028 Uiso 1 1 calc R . .
S29 S 0.26489(13) 0.41755(13) 0.37972(3) 0.0185(3) Uani 1 1 d . . .
C30 C 0.4566(5) 0.4733(6) 0.37467(14) 0.0236(11) Uani 1 1 d . . .
H30A H 0.4770 0.4686 0.3480 0.028 Uiso 1 1 calc R . .
H30B H 0.4728 0.5729 0.3836 0.028 Uiso 1 1 calc R . .
C31 C 0.5599(6) 0.3691(6) 0.39864(14) 0.0242(11) Uani 1 1 d . . .
H31A H 0.6578 0.4152 0.4038 0.029 Uiso 1 1 calc R . .
H31B H 0.5189 0.3545 0.4230 0.029 Uiso 1 1 calc R . .
C32 C 0.5821(5) 0.2213(5) 0.38086(14) 0.0203(11) Uani 1 1 d . . .
H32A H 0.6657 0.1751 0.3961 0.024 Uiso 1 1 calc R . .
H32B H 0.6159 0.2394 0.3558 0.024 Uiso 1 1 calc R . .
Cl1 Cl 0.83122(13) -0.24232(13) 0.38997(4) 0.0232(3) Uani 1 1 d . . .
O1 O 0.8038(5) -0.2333(5) 0.34932(11) 0.0450(11) Uani 1 1 d . . .
O2 O 0.9419(5) -0.3513(5) 0.39987(12) 0.0497(12) Uani 1 1 d . . .
O3 O 0.8825(5) -0.1038(5) 0.40445(15) 0.0545(13) Uani 1 1 d . . .
O4 O 0.6921(4) -0.2764(4) 0.40574(12) 0.0401(10) Uani 1 1 d . . .
Cl2 Cl 0.3408(8) 0.2757(6) 0.25870(15) 0.0160(13) Uani 0.65 1 d P A 1
O5 O 0.3623(10) 0.4154(9) 0.2420(2) 0.049(2) Uani 0.65 1 d P A 1
O6 O 0.4443(10) 0.1720(9) 0.2418(2) 0.048(2) Uani 0.65 1 d P A 1
O7 O 0.1900(12) 0.2254(13) 0.2488(4) 0.045(3) Uani 0.65 1 d P A 1
Cl2B Cl 0.3490(19) 0.2864(18) 0.2600(5) 0.052(5) Uani 0.35 1 d P A 2
O5B O 0.2764(18) 0.4263(15) 0.2573(4) 0.052(4) Uani 0.35 1 d P A 2
O6B O 0.4724(15) 0.278(2) 0.2414(4) 0.057(5) Uani 0.35 1 d P A 2
O7B O 0.238(2) 0.173(2) 0.2524(6) 0.027(4) Uani 0.35 1 d P A 2
O8 O 0.3845(4) 0.2774(4) 0.30027(10) 0.0307(9) Uani 1 1 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'
Cu Cu 0.3201 1.2651 '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'
S S 0.1246 0.1234 '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
N27 Cu N16 175.95(15) . . ?
N27 Cu S29 84.09(12) . . ?
N16 Cu S29 98.76(12) . . ?
N27 Cu S20 84.47(12) . . ?
N16 Cu S20 94.00(12) . . ?
S29 Cu S20 154.53(5) . . ?
N27 Cu O8 89.36(14) . . ?
N16 Cu O8 87.72(14) . . ?
S29 Cu O8 90.89(10) . . ?
S20 Cu O8 111.66(10) . . ?
C2 C1 C6 121.0(5) . . ?
C1 C2 C3 121.4(5) . . ?
C4 C3 C2 119.4(5) . . ?
C3 C4 C5 121.2(5) . . ?
C10 C5 C4 121.7(4) . . ?
C10 C5 C6 118.8(4) . . ?
C4 C5 C6 119.4(4) . . ?
C7 C6 C1 122.8(4) . . ?
C7 C6 C5 120.3(4) . . ?
C1 C6 C5 116.9(4) . . ?
C6 C7 C8 119.1(4) . . ?
C6 C7 C15 119.3(4) . . ?
C8 C7 C15 121.5(4) . . ?
C7 C8 C9 119.1(4) . . ?
C7 C8 C14 123.1(4) . . ?
C9 C8 C14 117.8(4) . . ?
C10 C9 C8 120.2(4) . . ?
C10 C9 C11 120.7(5) . . ?
C8 C9 C11 119.0(4) . . ?
C9 C10 C5 121.6(4) . . ?
C12 C11 C9 120.9(5) . . ?
C11 C12 C13 119.6(5) . . ?
C14 C13 C12 122.2(5) . . ?
C13 C14 C8 120.5(5) . . ?
C7 C15 N16 114.4(4) . . ?
C15 N16 C17 107.6(4) . . ?
C15 N16 C32 111.1(4) . . ?
C17 N16 C32 102.5(3) . . ?
C15 N16 Cu 112.6(3) . . ?
C17 N16 Cu 108.2(3) . . ?
C32 N16 Cu 114.1(3) . . ?
C18 C17 N16 119.3(4) . . ?
C17 C18 C19 114.3(4) . . ?
C18 C19 S20 106.0(3) . . ?
C21 S20 C19 105.1(2) . . ?
C21 S20 Cu 98.48(17) . . ?
C19 S20 Cu 100.94(17) . . ?
C22 C21 S20 112.6(3) . . ?
N27 C22 C23 121.1(4) . . ?
N27 C22 C21 117.9(4) . . ?
C23 C22 C21 120.8(4) . . ?
C24 C23 C22 119.3(5) . . ?
C23 C24 C25 119.7(5) . . ?
C26 C25 C24 119.1(5) . . ?
N27 C26 C25 121.9(5) . . ?
N27 C26 C28 116.1(4) . . ?
C25 C26 C28 121.9(4) . . ?
C26 N27 C22 118.8(4) . . ?
C26 N27 Cu 119.5(3) . . ?
C22 N27 Cu 121.6(3) . . ?
C26 C28 S29 109.7(3) . . ?
C28 S29 C30 103.9(2) . . ?
C28 S29 Cu 94.35(17) . . ?
C30 S29 Cu 102.29(17) . . ?
C31 C30 S29 107.2(3) . . ?
C32 C31 C30 115.4(4) . . ?
C31 C32 N16 122.7(4) . . ?
O2 Cl1 O3 110.2(3) . . ?
O2 Cl1 O1 109.5(2) . . ?
O3 Cl1 O1 108.9(3) . . ?
O2 Cl1 O4 110.9(3) . . ?
O3 Cl1 O4 108.4(2) . . ?
O1 Cl1 O4 108.9(3) . . ?
O5 Cl2 O7 110.3(7) . . ?
O5 Cl2 O8 111.4(5) . . ?
O7 Cl2 O8 113.4(7) . . ?
O5 Cl2 O6 107.2(6) . . ?
O7 Cl2 O6 107.5(7) . . ?
O8 Cl2 O6 106.6(5) . . ?
O6B Cl2B O8 111.6(13) . . ?
O6B Cl2B O5B 113.9(17) . . ?
O8 Cl2B O5B 100.1(12) . . ?
O6B Cl2B O7B 116.8(17) . . ?
O8 Cl2B O7B 103.1(13) . . ?
O5B Cl2B O7B 109.5(14) . . ?
Cl2B O8 Cl2 4.6(9) . . ?
Cl2B O8 Cu 133.9(7) . . ?
Cl2 O8 Cu 130.1(3) . . ?
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
Cu N27 2.008(4) . ?
Cu N16 2.057(4) . ?
Cu S29 2.3114(15) . ?
Cu S20 2.3223(15) . ?
Cu O8 2.364(3) . ?
C1 C2 1.358(7) . ?
C1 C6 1.432(6) . ?
C2 C3 1.407(7) . ?
C3 C4 1.359(7) . ?
C4 C5 1.419(6) . ?
C5 C10 1.392(6) . ?
C5 C6 1.433(7) . ?
C6 C7 1.419(6) . ?
C7 C8 1.424(6) . ?
C7 C15 1.493(6) . ?
C8 C9 1.431(7) . ?
C8 C14 1.432(6) . ?
C9 C10 1.391(7) . ?
C9 C11 1.434(7) . ?
C11 C12 1.361(7) . ?
C12 C13 1.400(8) . ?
C13 C14 1.356(7) . ?
C15 N16 1.516(6) . ?
N16 C17 1.518(6) . ?
N16 C32 1.520(6) . ?
C17 C18 1.511(7) . ?
C18 C19 1.516(7) . ?
C19 S20 1.817(5) . ?
S20 C21 1.809(5) . ?
C21 C22 1.495(7) . ?
C22 N27 1.360(6) . ?
C22 C23 1.380(7) . ?
C23 C24 1.373(7) . ?
C24 C25 1.376(7) . ?
C25 C26 1.372(6) . ?
C26 N27 1.348(6) . ?
C26 C28 1.507(7) . ?
C28 S29 1.805(5) . ?
S29 C30 1.806(5) . ?
C30 C31 1.521(7) . ?
C31 C32 1.509(7) . ?
Cl1 O2 1.421(4) . ?
Cl1 O3 1.424(4) . ?
Cl1 O1 1.426(4) . ?
Cl1 O4 1.437(4) . ?
Cl2 O5 1.426(9) . ?
Cl2 O7 1.430(14) . ?
Cl2 O8 1.474(7) . ?
Cl2 O6 1.483(9) . ?
Cl2B O6B 1.332(19) . ?
Cl2B O8 1.420(16) . ?
Cl2B O5B 1.43(2) . ?
Cl2B O7B 1.44(3) . ?
