#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:37:18 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179980 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/74/7027443.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7027443
loop_
_publ_author_name
'Cronin, Leroy'
'Mount, Andrew R.'
'Parsons, Simon'
'Robertson, Neil'
_publ_section_title
;
 A new class of macrocycle capable of binding exogenous metals: synthesis,
 structure, magnetic and electrochemical properties of a Cu(II) trinuclear
 complex based upon 1,4,8,11-tetraazacyclotetradecane-2,3-dione
 [exoO2]cyclam †
;
_journal_issue                   12
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              1925
_journal_paper_doi               10.1039/a902792k
_journal_year                    1999
_chemical_formula_moiety         '2 (Cl O4) C20 H44 Cu3 N8 O6'
_chemical_formula_sum            'C20 H44 Cl2 Cu3 N8 O16'
_chemical_formula_weight         914.16
_chemical_name_common            {Cu[exoO₂cyclam]}₂Cu(ClO4)₂2H₂O
_chemical_name_systematic
;[((1,4,8,11-tetraaza-κ⁴N)-cyclotetradecane-2,3-
dione-(hydrato-/kO)copper(II))2-κ⁴O-copper(II))]
bis perchlorate dihydrate
;
_chemical_temperature_decomposition_gt 160
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 106.208(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6599(17)
_cell_length_b                   16.907(4)
_cell_length_c                   12.784(2)
_cell_measurement_reflns_used    56
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      66
_cell_measurement_theta_min      60
_cell_volume                     1797.3(6)
_computing_molecular_graphics    'WINGX PACKAGE (L. J. Farrugia, 1998)'
_computing_publication_material  'WINGX PACKAGE (L. J. Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (A. Guagliardi, 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'Stoe Stadi-4B'
_diffrn_measurement_method       ωθ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3746
_diffrn_reflns_theta_full        70.07
_diffrn_reflns_theta_max         70.07
_diffrn_reflns_theta_min         4.45
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.113
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_correction_T_min  0.653
_exptl_absorpt_correction_type   'empirical via \y scans'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             938
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       'none refined'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3171
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0555
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0987P)²+0.9945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1532
_reflns_number_gt                2553
_reflns_number_total             3171
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            902792ksup1.cif
_cod_data_source_block           lc112f
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition_gt' since the value was
specified 'more than' ('>') a certain temperature. The value '>160
(dec.)' was changed to '160' - it should be numeric and without a
unit designator.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1797.4(6)
_cod_original_sg_symbol_H-M      'P 21 / n'
_cod_database_code               7027443
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Cu1 Cu 1.0000 0.5000 0.5000 0.0402(3) Uani 1 2 d S
Cu2 Cu 1.46797(6) 0.34872(4) 0.76150(4) 0.0376(2) Uani 1 1 d .
O1 O 1.2031(3) 0.45600(17) 0.4935(2) 0.0400(6) Uani 1 1 d .
O2 O 1.0338(3) 0.44284(18) 0.6355(2) 0.0427(7) Uani 1 1 d .
O3 O 1.6165(5) 0.4762(2) 0.8326(4) 0.0701(11) Uani 1 1 d .
HC H 1.564(10) 0.508(5) 0.834(8) 0.105 Uiso 1 1 d .
N1 N 1.2523(4) 0.3859(2) 0.7585(2) 0.0367(7) Uani 1 1 d .
N2 N 1.4126(4) 0.3881(2) 0.6117(2) 0.0357(7) Uani 1 1 d .
N3 N 1.6563(4) 0.2841(3) 0.7488(3) 0.0501(9) Uani 1 1 d .
HA H 1.639(7) 0.236(4) 0.722(5) 0.075 Uiso 1 1 d .
N4 N 1.5358(5) 0.3170(2) 0.9191(3) 0.0477(9) Uani 1 1 d .
HB H 1.595(7) 0.361(3) 0.954(5) 0.072 Uiso 1 1 d .
C1 C 1.1776(4) 0.4160(2) 0.6659(3) 0.0340(8) Uani 1 1 d .
C2 C 1.2733(4) 0.4211(2) 0.5834(3) 0.0317(7) Uani 1 1 d .
C3 C 1.5194(5) 0.3922(3) 0.5414(3) 0.0433(9) Uani 1 1 d .
H3A H 1.5803 0.4410 0.5559 0.052 Uiso 1 1 calc R
H3B H 1.4551 0.3931 0.4659 0.052 Uiso 1 1 calc R
C4 C 1.6344(6) 0.3236(4) 0.5580(4) 0.0624(14) Uani 1 1 d .
H4A H 1.7015 0.3299 0.5092 0.075 Uiso 1 1 calc R
H4B H 1.5726 0.2754 0.5371 0.075 Uiso 1 1 calc R
C5 C 1.7426(5) 0.3134(4) 0.6727(4) 0.0569(13) Uani 1 1 d .
H5A H 1.8280 0.2766 0.6714 0.068 Uiso 1 1 calc R
H5B H 1.7917 0.3639 0.6987 0.068 Uiso 1 1 calc R
C6 C 1.7585(6) 0.2687(3) 0.8583(4) 0.0553(12) Uani 1 1 d .
H6A H 1.8276 0.3138 0.8844 0.066 Uiso 1 1 calc R
H6B H 1.8260 0.2230 0.8576 0.066 Uiso 1 1 calc R
C7 C 1.6537(6) 0.2535(3) 0.9323(4) 0.0540(11) Uani 1 1 d .
H7A H 1.5991 0.2031 0.9144 0.065 Uiso 1 1 calc R
H7B H 1.7193 0.2514 1.0074 0.065 Uiso 1 1 calc R
C8 C 1.4057(5) 0.3024(3) 0.9698(3) 0.0506(11) Uani 1 1 d .
H8A H 1.4523 0.2922 1.0468 0.061 Uiso 1 1 calc R
H8B H 1.3471 0.2555 0.9376 0.061 Uiso 1 1 calc R
C9 C 1.2905(6) 0.3704(3) 0.9565(4) 0.0528(11) Uani 1 1 d .
H9A H 1.3520 0.4190 0.9724 0.063 Uiso 1 1 calc R
H9B H 1.2308 0.3650 1.0100 0.063 Uiso 1 1 calc R
C10 C 1.1711(5) 0.3779(3) 0.8444(3) 0.0476(10) Uani 1 1 d .
H10A H 1.1026 0.3314 0.8301 0.057 Uiso 1 1 calc R
H10B H 1.1033 0.4237 0.8433 0.057 Uiso 1 1 calc R
Cl1 Cl 1.29098(18) 0.63432(8) 0.75475(11) 0.0683(4) Uani 1 1 d D
O4 O 1.3306(6) 0.5753(3) 0.8382(4) 0.0870(13) Uani 1 1 d D
O5 O 1.1916(6) 0.6048(3) 0.6552(4) 0.0954(14) Uani 1 1 d D
O6 O 1.2171(10) 0.6982(3) 0.7917(5) 0.144(3) Uani 1 1 d D
O7A O 1.4346(15) 0.6674(9) 0.7433(12) 0.130(6) Uani 0.70 1 d PD
O7B O 1.427(2) 0.651(3) 0.719(3) 0.144(17) Uani 0.30 1 d PD
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'
Cu Cu -1.9646 0.5888 '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
O2 Cu1 O2 180.000(1) . 3_766
O2 Cu1 O1 86.24(11) . .
O2 Cu1 O1 93.76(11) 3_766 .
O2 Cu1 O1 93.76(11) . 3_766
O2 Cu1 O1 86.24(11) 3_766 3_766
O1 Cu1 O1 180.000(1) . 3_766
N2 Cu2 N1 84.28(13) . .
N2 Cu2 N3 95.06(14) . .
N1 Cu2 N3 164.59(17) . .
N2 Cu2 N4 175.02(16) . .
N1 Cu2 N4 96.62(15) . .
N3 Cu2 N4 85.37(16) . .
N2 Cu2 O3 91.31(15) . .
N1 Cu2 O3 96.84(14) . .
N3 Cu2 O3 98.57(16) . .
N4 Cu2 O3 83.72(16) . .
C2 O1 Cu1 110.3(2) . .
C1 O2 Cu1 109.9(2) . .
C1 N1 C10 120.2(3) . .
C1 N1 Cu2 112.1(2) . .
C10 N1 Cu2 127.5(3) . .
C2 N2 C3 120.8(3) . .
C2 N2 Cu2 112.2(2) . .
C3 N2 Cu2 126.5(2) . .
C6 N3 C5 114.4(4) . .
C6 N3 Cu2 108.0(3) . .
C5 N3 Cu2 116.4(3) . .
C7 N4 C8 115.0(4) . .
C7 N4 Cu2 108.2(3) . .
C8 N4 Cu2 116.2(3) . .
O2 C1 N1 128.1(3) . .
O2 C1 C2 116.3(3) . .
N1 C1 C2 115.6(3) . .
O1 C2 N2 128.6(3) . .
O1 C2 C1 115.8(3) . .
N2 C2 C1 115.6(3) . .
N2 C3 C4 112.6(4) . .
C3 C4 C5 115.5(4) . .
N3 C5 C4 112.9(4) . .
N3 C6 C7 108.9(4) . .
N4 C7 C6 109.1(4) . .
N4 C8 C9 112.9(4) . .
C8 C9 C10 115.2(4) . .
N1 C10 C9 111.8(3) . .
O6 Cl1 O7B 117.2(19) . .
O6 Cl1 O7A 103.2(8) . .
O7B Cl1 O7A 17(2) . .
O6 Cl1 O5 110.8(4) . .
O7B Cl1 O5 97.8(16) . .
O7A Cl1 O5 112.4(7) . .
O6 Cl1 O4 108.8(3) . .
O7B Cl1 O4 109.4(15) . .
O7A Cl1 O4 108.7(6) . .
O5 Cl1 O4 112.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.933(3) .
Cu1 O2 1.933(3) 3_766
Cu1 O1 1.933(3) .
Cu1 O1 1.933(3) 3_766
Cu2 N2 1.957(3) .
Cu2 N1 1.961(3) .
Cu2 N3 2.007(4) .
Cu2 N4 2.007(4) .
Cu2 O3 2.545(4) .
O1 C2 1.284(4) .
O2 C1 1.280(5) .
N1 C1 1.285(5) .
N1 C10 1.466(5) .
N2 C2 1.287(5) .
N2 C3 1.460(5) .
N3 C6 1.456(5) .
N3 C5 1.468(6) .
N4 C7 1.459(6) .
N4 C8 1.469(6) .
C1 C2 1.515(5) .
C3 C4 1.505(7) .
C4 C5 1.513(6) .
C6 C7 1.505(7) .
C8 C9 1.500(7) .
C9 C10 1.520(6) .
Cl1 O6 1.402(5) .
Cl1 O7B 1.402(14) .
Cl1 O7A 1.408(9) .
Cl1 O5 1.414(4) .
Cl1 O4 1.431(4) .
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
O3 HC O4 0.71(8) 2.34(8) 3.007(6) 160(9)
