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#$Date: 2025-08-21 00:01:10 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301838 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/79/4327976.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_4327976
loop_
_publ_author_name
'Linda Tjioe'
'Tanmaya Joshi'
'Craig M. Forsyth'
'Boujemaa Moubaraki'
'Keith S. Murray'
'Joël Brugger'
'Bim Graham'
'Leone Spiccia'
_publ_contact_author_address
;Monash University
School of Chemistry
Wellington Rd
Clayton
Victoria, Australia, 3800
;
_publ_contact_author_email       leone.spiccia@monash.edu
_publ_contact_author_fax         +610399054597
_publ_contact_author_name        'Leone Spiccia'
_publ_contact_author_phone       +610399054526
_publ_section_title
;
 Phosphodiester Cleavage Properties of Copper(II) Complexes of
 1,4,7-Triazacyclononane Ligands Bearing Single Alkyl Guanidine Pendants
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              939
_journal_page_last               953
_journal_paper_doi               10.1021/ic2019814
_journal_volume                  51
_journal_year                    2012
_chemical_formula_moiety         'C18 H45 Cu2 N12 O1, 3(Cl O4)'
_chemical_formula_sum            'C18 H45 Cl3 Cu2 N12 O13'
_chemical_formula_weight         871.09
_chemical_name_common
(1-(2-Guanidinoethyl)-1,4,7-triazacyclononane)copper(II)perchlorate
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                   10.6042(11)
_cell_length_b                   17.6925(16)
_cell_length_c                   17.6100(17)
_cell_measurement_temperature    123(2)
_cell_volume                     3303.9(6)
_computing_cell_refinement       'Bruker apex2 v2.0'
_computing_data_collection       'Bruker apex2 v2.0'
_computing_data_reduction        'Bruker apex2 v2.0'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker X8 Apex CCD'
_diffrn_measurement_method       'thin slice phi scan'
_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  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10302
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.609
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_description       prism
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2728
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0366
_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)+(0.0545P)²+4.4641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.1019
_reflns_number_gt                2186
_reflns_number_total             2728
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic2019814_si_001_2.cif
_cod_data_source_block           C1
_cod_database_code               4327976
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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 0.90832(4) 0.17913(3) 0.16214(2) 0.01856(16) Uani 1 1 d .
Cl1 Cl 1.18075(9) 0.56372(6) 0.10044(5) 0.0288(2) Uani 1 1 d .
Cl2 Cl 0.5000 0.35457(8) 0.2500 0.0251(3) Uani 1 2 d S
O1 O 1.0000 0.1413(2) 0.2500 0.0219(8) Uani 1 2 d SD
H1 H 1.0000 0.0876 0.2500 0.026 Uiso 1 2 calc SRD
O2 O 1.2616(4) 0.5407(3) 0.16017(17) 0.0760(13) Uani 1 1 d .
O3 O 1.2522(3) 0.5605(3) 0.03288(18) 0.0752(13) Uani 1 1 d .
O4 O 1.1365(4) 0.6382(2) 0.1100(3) 0.103(2) Uani 1 1 d .
O5 O 1.0750(3) 0.51504(18) 0.0938(2) 0.0564(10) Uani 1 1 d .
O6 O 0.6085(3) 0.40008(18) 0.23559(19) 0.0450(8) Uani 1 1 d .
O7 O 0.4739(3) 0.30757(19) 0.18562(16) 0.0410(8) Uani 1 1 d .
N1 N 0.7906(3) 0.22346(18) 0.08271(16) 0.0222(7) Uani 1 1 d .
N2 N 0.7685(3) 0.10149(19) 0.17711(17) 0.0247(7) Uani 1 1 d D
N3 N 0.9602(3) 0.10186(19) 0.06586(17) 0.0258(7) Uani 1 1 d D
N4 N 0.9951(3) 0.27863(18) 0.15097(15) 0.0208(7) Uani 1 1 d .
N5 N 1.1574(3) 0.3677(2) 0.1585(2) 0.0344(9) Uani 1 1 d D
N6 N 1.1930(3) 0.2460(2) 0.19514(18) 0.0250(7) Uani 1 1 d D
C1 C 0.6634(3) 0.1864(2) 0.0875(2) 0.0270(9) Uani 1 1 d .
H1A H 0.6530 0.1505 0.0449 0.032 Uiso 1 1 calc R
H1B H 0.5964 0.2252 0.0836 0.032 Uiso 1 1 calc R
C2 C 0.6512(4) 0.1446(2) 0.1624(2) 0.0293(9) Uani 1 1 d .
H2A H 0.6365 0.1811 0.2041 0.035 Uiso 1 1 calc R
H2B H 0.5785 0.1096 0.1604 0.035 Uiso 1 1 calc R
C3 C 0.7837(4) 0.0342(2) 0.1265(2) 0.0295(9) Uani 1 1 d .
H3A H 0.7231 0.0378 0.0839 0.035 Uiso 1 1 calc R
H3B H 0.7639 -0.0122 0.1556 0.035 Uiso 1 1 calc R
C4 C 0.9163(4) 0.0285(2) 0.0951(2) 0.0299(9) Uani 1 1 d .
H4A H 0.9741 0.0111 0.1356 0.036 Uiso 1 1 calc R
H4B H 0.9181 -0.0093 0.0537 0.036 Uiso 1 1 calc R
C5 C 0.8925(4) 0.1302(2) -0.0024(2) 0.0313(10) Uani 1 1 d .
H5A H 0.8176 0.0982 -0.0120 0.038 Uiso 1 1 calc R
H5B H 0.9486 0.1266 -0.0471 0.038 Uiso 1 1 calc R
C6 C 0.8513(4) 0.2113(2) 0.00800(19) 0.0286(9) Uani 1 1 d .
H6A H 0.9256 0.2448 0.0035 0.034 Uiso 1 1 calc R
H6B H 0.7912 0.2249 -0.0328 0.034 Uiso 1 1 calc R
C7 C 0.7825(4) 0.3043(2) 0.1051(2) 0.0271(9) Uani 1 1 d .
H7A H 0.7317 0.3089 0.1521 0.033 Uiso 1 1 calc R
H7B H 0.7397 0.3333 0.0646 0.033 Uiso 1 1 calc R
C8 C 0.9135(4) 0.3370(2) 0.1187(2) 0.0282(9) Uani 1 1 d .
H8A H 0.9494 0.3552 0.0701 0.034 Uiso 1 1 calc R
H8B H 0.9079 0.3804 0.1540 0.034 Uiso 1 1 calc R
C9 C 1.1111(3) 0.2977(2) 0.16706(19) 0.0246(9) Uani 1 1 d .
H2 H 0.767(4) 0.084(2) 0.2231(11) 0.037(12) Uiso 1 1 d D
H3 H 1.0405(13) 0.098(2) 0.056(2) 0.025(10) Uiso 1 1 d D
H6D H 1.2735(13) 0.255(2) 0.187(2) 0.025(11) Uiso 1 1 d D
H5D H 1.2318(18) 0.379(2) 0.1771(19) 0.022(10) Uiso 1 1 d D
H5C H 1.107(4) 0.4054(18) 0.149(3) 0.047(15) Uiso 1 1 d D
H6C H 1.173(4) 0.1984(9) 0.188(2) 0.029(12) Uiso 1 1 d 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'
N N 0.0061 0.0033 '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'
Cu Cu 0.3201 1.2651 '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'
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
O1 Cu1 N4 98.71(12) . .
O1 Cu1 N1 170.70(9) . .
N4 Cu1 N1 82.82(12) . .
O1 Cu1 N2 91.64(11) . .
N4 Cu1 N2 160.47(13) . .
N1 Cu1 N2 84.41(12) . .
O1 Cu1 N3 105.57(11) . .
N4 Cu1 N3 110.46(12) . .
N1 Cu1 N3 82.28(12) . .
N2 Cu1 N3 82.27(13) . .
O4 Cl1 O3 108.5(3) . .
O4 Cl1 O2 112.5(3) . .
O3 Cl1 O2 106.8(2) . .
O4 Cl1 O5 108.3(2) . .
O3 Cl1 O5 109.3(2) . .
O2 Cl1 O5 111.4(2) . .
O6 Cl2 O6 111.3(3) . 4_655
O6 Cl2 O7 108.21(17) . 4_655
O6 Cl2 O7 110.01(18) 4_655 4_655
O6 Cl2 O7 110.01(18) . .
O6 Cl2 O7 108.21(17) 4_655 .
O7 Cl2 O7 109.1(3) 4_655 .
Cu1 O1 Cu1 139.8(2) 4_755 .
C6 N1 C7 113.7(3) . .
C6 N1 C1 112.1(3) . .
C7 N1 C1 110.7(3) . .
C6 N1 Cu1 106.8(2) . .
C7 N1 Cu1 103.0(2) . .
C1 N1 Cu1 110.1(2) . .
C2 N2 C3 113.3(3) . .
C2 N2 Cu1 104.0(2) . .
C3 N2 Cu1 112.4(2) . .
C4 N3 C5 115.4(3) . .
C4 N3 Cu1 101.3(2) . .
C5 N3 Cu1 106.6(2) . .
C9 N4 C8 117.3(3) . .
C9 N4 Cu1 129.9(3) . .
C8 N4 Cu1 112.8(2) . .
N1 C1 C2 109.8(3) . .
N2 C2 C1 109.3(3) . .
N2 C3 C4 111.7(3) . .
N3 C4 C3 111.3(3) . .
N3 C5 C6 111.3(3) . .
N1 C6 C5 111.8(3) . .
N1 C7 C8 110.7(3) . .
N4 C8 C7 109.4(3) . .
N4 C9 N5 124.0(4) . .
N4 C9 N6 120.5(4) . .
N5 C9 N6 115.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9461(13) .
Cu1 N4 1.996(3) .
Cu1 N1 2.032(3) .
Cu1 N2 2.038(3) .
Cu1 N3 2.246(3) .
Cl1 O4 1.409(4) .
Cl1 O3 1.412(3) .
Cl1 O2 1.417(4) .
Cl1 O5 1.419(3) .
Cl2 O6 1.427(3) .
Cl2 O6 1.427(3) 4_655
Cl2 O7 1.433(3) 4_655
Cl2 O7 1.433(3) .
O1 Cu1 1.9461(13) 4_755
N1 C6 1.480(4) .
N1 C7 1.486(5) .
N1 C1 1.503(5) .
N2 C2 1.482(5) .
N2 C3 1.495(5) .
N3 C4 1.471(5) .
N3 C5 1.487(5) .
N4 C9 1.307(5) .
N4 C8 1.462(5) .
N5 C9 1.340(5) .
N6 C9 1.355(5) .
C1 C2 1.518(5) .
C3 C4 1.515(6) .
C5 C6 1.509(6) .
C7 C8 1.524(5) .
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
_geom_hbond_site_symmetry_A
N2 H2 O2 0.870(10) 2.192(11) 3.062(4) 179(4) 6_556
N3 H3 O3 0.873(10) 2.330(14) 3.190(5) 168(3) 7_855
N5 H5C O5 0.873(10) 2.19(3) 2.976(5) 149(4) .
N5 H5D O6 0.877(10) 2.318(16) 3.158(5) 160(3) 4_755
N6 H6D O7 0.879(10) 2.319(15) 3.177(4) 165(4) 1_655
N6 H6C O1 0.878(10) 2.36(3) 2.925(4) 122(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139136841
