#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:06:12 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179093 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/55/4305566.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_4305566
loop_
_publ_author_name
'Enrico Arturoni'
'Carla Bazzicalupi'
'Andrea Bencini'
'Claudia Caltagirone'
'Andrea Danesi'
'Alessandra Garau'
'Claudia Giorgi'
'Vito Lippolis'
'Barbara Valtancoli'
_publ_contact_author_address
;  Department of Chemistry
   University of Florence
   Via della Lastruccia 3
   50019 Sesto Fiorentino
   Florence
   Italy
;
_publ_contact_author_email       andrea.bencini@unifi.it
_publ_contact_author_fax         39(055)4573364
_publ_contact_author_phone       39(055)4573371
_publ_section_title
;
New Bis-Cresol-Bridged bis(1,4,7-Triazacyclononane) Ligand As Receptor for
Metal Cations and Phosphate Anions
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6551
_journal_page_last               6563
_journal_paper_doi               10.1021/ic800549e
_journal_volume                  47
_journal_year                    2008
_chemical_formula_sum            'C29 H48 Cu2 N8 O10'
_chemical_formula_weight         795.84
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           52
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2a 2bc'
_symmetry_space_group_name_H-M   'P n n a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.05230(10)
_cell_length_b                   28.3800(4)
_cell_length_c                   16.1372(2)
_cell_measurement_reflns_used    9788
_cell_measurement_temperature    298
_cell_measurement_theta_max      72.1834
_cell_measurement_theta_min      4.1469
_cell_volume                     3687.74(8)
_computing_cell_refinement       'Crysalis CCD - Oxford diffraction'
_computing_data_collection       'Crysalis CCD - Oxford diffraction'
_computing_data_reduction        'Crysalis CCD - Oxford diffraction'
_computing_molecular_graphics
;
ORTEP3 Ver. 1.01β (Farrugia, 1997) - Mercury 2001-2007
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla 2005)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 8.1241
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24113
_diffrn_reflns_theta_full        72.32
_diffrn_reflns_theta_max         72.32
_diffrn_reflns_theta_min         5.42
_diffrn_standards_interval_count infinity
_diffrn_standards_interval_time  infinity
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.953
_exptl_absorpt_correction_T_max  0.677
_exptl_absorpt_correction_T_min  0.374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.2 (release 07-07-2006 CrysAlis171 .NET)
(compiled Jul 10 2006,00:11:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.263
_refine_diff_density_min         -1.374
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.363
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3606
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.381
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0677
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1278P)²+0.9021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2081
_refine_ls_wR_factor_ref         0.2358
_reflns_number_gt                2682
_reflns_number_total             3606
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic800549e-file005.cif
_cod_data_source_block           '[Cu2L(NO3)2].2H2O'
_cod_database_code               4305566
loop_
_publ_contact_author_name
'Prof. Andrea Bencini'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z'
'x, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'-x, y-1/2, z-1/2'
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.65670(7) 0.115345(19) 0.27302(3) 0.0439(3) Uani 1 1 d . . .
O1 O 0.8236(3) 0.15988(10) 0.30707(19) 0.0480(7) Uani 1 1 d . . .
O3 O 0.7781(5) 0.09954(11) 0.17044(18) 0.0582(8) Uani 1 1 d . . .
N2 N 0.5230(4) 0.12311(12) 0.3813(2) 0.0478(8) Uani 1 1 d . . .
C9 C 0.8320(4) 0.24341(15) 0.3268(2) 0.0411(8) Uani 1 1 d . . .
C11 C 0.6820(5) 0.19310(15) 0.4230(2) 0.0472(9) Uani 1 1 d . . .
N3 N 0.5045(5) 0.05865(13) 0.2543(3) 0.0558(9) Uani 1 1 d . . .
H3 H 0.5688 0.0332 0.2419 0.067 Uiso 1 1 calc R . .
N1 N 0.4361(5) 0.15371(15) 0.2185(2) 0.0586(10) Uani 1 1 d . . .
H1 H 0.4678 0.1726 0.1758 0.070 Uiso 1 1 calc R . .
C12 C 0.7798(5) 0.19775(14) 0.3510(2) 0.0431(9) Uani 1 1 d . . .
C10 C 0.6819(5) 0.27802(16) 0.4442(3) 0.0511(10) Uani 1 1 d . . .
C3 C 0.3696(5) 0.15188(17) 0.3679(3) 0.0557(11) Uani 1 1 d . . .
H3A H 0.3522 0.1722 0.4155 0.067 Uiso 1 1 calc R . .
H3B H 0.2745 0.1310 0.3634 0.067 Uiso 1 1 calc R . .
C7 C 0.7804(5) 0.28186(15) 0.3735(2) 0.0471(9) Uani 1 1 d . . .
H7 H 0.8134 0.3118 0.3567 0.057 Uiso 1 1 calc R . .
C4 C 0.6289(6) 0.14452(16) 0.4474(2) 0.0518(10) Uani 1 1 d . . .
H4A H 0.7262 0.1250 0.4563 0.062 Uiso 1 1 calc R . .
H4B H 0.5670 0.1459 0.4989 0.062 Uiso 1 1 calc R . .
C5 C 0.6334(5) 0.23272(17) 0.4677(2) 0.0511(10) Uani 1 1 d . . .
H5 H 0.5671 0.2289 0.5144 0.061 Uiso 1 1 calc R . .
O2 O 0.9165(7) 0.03829(14) 0.2188(2) 0.0882(13) Uani 1 1 d . . .
C8 C 0.9361(7) 0.2500 0.2500 0.0472(13) Uani 1 2 d S . .
H8A H 1.0070 0.2227 0.2427 0.057 Uiso 0.50 1 calc PR . .
H8B H 1.0070 0.2773 0.2573 0.057 Uiso 0.50 1 calc PR . .
N4 N 0.8767(6) 0.06420(17) 0.1569(3) 0.0741(12) Uani 1 1 d D . .
C2 C 0.3815(6) 0.18193(18) 0.2899(3) 0.0608(12) Uani 1 1 d . . .
H2A H 0.2739 0.1957 0.2781 0.073 Uiso 1 1 calc R . .
H2B H 0.4597 0.2074 0.2991 0.073 Uiso 1 1 calc R . .
C1 C 0.3158(8) 0.11727(19) 0.1902(4) 0.0717(15) Uani 1 1 d . . .
H1C H 0.2686 0.1267 0.1374 0.086 Uiso 1 1 calc R . .
H1D H 0.2261 0.1146 0.2300 0.086 Uiso 1 1 calc R . .
C14 C 0.4092(6) 0.04800(17) 0.3304(3) 0.0611(12) Uani 1 1 d . . .
H14A H 0.4100 0.0143 0.3403 0.073 Uiso 1 1 calc R . .
H14B H 0.2947 0.0579 0.3232 0.073 Uiso 1 1 calc R . .
C15 C 0.4012(7) 0.0699(2) 0.1809(3) 0.0694(14) Uani 1 1 d . . .
H15A H 0.3181 0.0455 0.1736 0.083 Uiso 1 1 calc R . .
H15B H 0.4708 0.0703 0.1318 0.083 Uiso 1 1 calc R . .
C6 C 0.6289(8) 0.3207(2) 0.4930(4) 0.0759(16) Uani 1 1 d . . .
H6A H 0.5099 0.3216 0.4964 0.114 Uiso 1 1 calc R . .
H6B H 0.6680 0.3487 0.4658 0.114 Uiso 1 1 calc R . .
H6C H 0.6750 0.3191 0.5478 0.114 Uiso 1 1 calc R . .
C13 C 0.4841(7) 0.07330(16) 0.4041(3) 0.0624(12) Uani 1 1 d . . .
H13A H 0.4065 0.0728 0.4501 0.075 Uiso 1 1 calc R . .
H13B H 0.5848 0.0573 0.4214 0.075 Uiso 1 1 calc R . .
O4 O 0.9242(10) 0.0545(3) 0.0832(3) 0.158(3) Uani 1 1 d D . .
O5 O 0.9947(5) 0.08252(16) 0.3677(3) 0.0905(13) 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 0.0181 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'
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
_geom_angle_publ_flag
O1 Cu O3 92.45(14) . . ?
O1 Cu N3 167.73(15) . . ?
O3 Cu N3 89.66(16) . . ?
O1 Cu N2 93.00(13) . . ?
O3 Cu N2 172.92(14) . . ?
N3 Cu N2 84.07(15) . . ?
O1 Cu N1 110.08(14) . . ?
O3 Cu N1 99.93(14) . . ?
N3 Cu N1 81.41(15) . . ?
N2 Cu N1 82.41(15) . . ?
C12 O1 Cu 119.7(2) . . ?
N4 O3 Cu 128.3(3) . . ?
C4 N2 C3 110.7(3) . . ?
C4 N2 C13 109.2(3) . . ?
C3 N2 C13 112.3(4) . . ?
C4 N2 Cu 110.5(3) . . ?
C3 N2 Cu 111.5(3) . . ?
C13 N2 Cu 102.5(3) . . ?
C7 C9 C12 118.7(3) . . ?
C7 C9 C8 121.0(3) . . ?
C12 C9 C8 120.3(3) . . ?
C5 C11 C12 120.6(4) . . ?
C5 C11 C4 121.8(4) . . ?
C12 C11 C4 117.6(4) . . ?
C15 N3 C14 114.6(4) . . ?
C15 N3 Cu 106.6(3) . . ?
C14 N3 Cu 110.4(3) . . ?
C1 N1 C2 115.2(4) . . ?
C1 N1 Cu 107.2(3) . . ?
C2 N1 Cu 101.1(3) . . ?
O1 C12 C11 120.6(4) . . ?
O1 C12 C9 120.8(3) . . ?
C11 C12 C9 118.6(4) . . ?
C7 C10 C5 117.0(4) . . ?
C7 C10 C6 121.7(4) . . ?
C5 C10 C6 121.3(4) . . ?
N2 C3 C2 111.9(4) . . ?
C9 C7 C10 123.5(4) . . ?
N2 C4 C11 110.5(3) . . ?
C10 C5 C11 121.6(4) . . ?
C9 C8 C9 112.4(4) . 3 ?
O2 N4 O3 117.7(4) . . ?
O2 N4 O4 121.8(6) . . ?
O3 N4 O4 120.4(5) . . ?
N1 C2 C3 111.2(4) . . ?
N1 C1 C15 110.5(5) . . ?
N3 C14 C13 110.4(4) . . ?
N3 C15 C1 111.5(4) . . ?
N2 C13 C14 109.8(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
Cu O1 1.925(3) . ?
Cu O3 1.974(3) . ?
Cu N3 2.045(4) . ?
Cu N2 2.065(4) . ?
Cu N1 2.262(4) . ?
O1 C12 1.335(5) . ?
O3 N4 1.298(6) . ?
N2 C4 1.495(5) . ?
N2 C3 1.496(5) . ?
N2 C13 1.494(5) . ?
C9 C7 1.390(6) . ?
C9 C12 1.417(6) . ?
C9 C8 1.507(5) . ?
C11 C5 1.393(6) . ?
C11 C12 1.410(6) . ?
C11 C4 1.496(6) . ?
N3 C15 1.482(7) . ?
N3 C14 1.480(6) . ?
N1 C1 1.489(7) . ?
N1 C2 1.470(6) . ?
C10 C7 1.394(6) . ?
C10 C5 1.396(7) . ?
C10 C6 1.507(7) . ?
C3 C2 1.523(7) . ?
O2 N4 1.281(6) . ?
C8 C9 1.507(5) 3 ?
N4 O4 1.279(2) . ?
C1 C15 1.518(8) . ?
C14 C13 1.515(7) . ?
