#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/50/2225095.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2225095
loop_
_publ_author_name
'Zhang, Zhong'
'Lu, Jianqi'
'Wu, Difeng'
_publ_section_title
;Tris(propionitrile-κN)[1,4,7-tris(cyanomethyl)-1,4,7-triazacyclononane-κ³N¹,N⁴,N⁷]copper(II)
 bis(perchlorate) dihydrate
;
_journal_coeditor_code           RK2185
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m235
_journal_page_last               m236
_journal_paper_doi               10.1107/S1600536810003211
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac
'[Cu (C3 H5 N)3 (C12 H18 N6)] (Cl O4)2, 2H2 O'
_chemical_formula_moiety         'C21 H33 Cu N9 2+, 2(Cl O4 -), 2(H2 O)'
_chemical_formula_sum            'C21 H37 Cl2 Cu N9 O10'
_chemical_formula_weight         710.05
_chemical_name_systematic
;Tris(propionitrile-κN)[1,4,7-tris(cyanomethyl)-1,4,7-triazacyclononane-
κ³N¹,N⁴,N⁷]copper(II)
 bis(perchlorate) dihydrate
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   9.962(2)
_cell_length_b                   9.962(2)
_cell_length_c                   61.623(18)
_cell_measurement_reflns_used    1799
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.92
_cell_measurement_theta_min      2.38
_cell_volume                     5296(2)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       64
_diffrn_reflns_limit_l_min       -75
_diffrn_reflns_number            9484
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  0.887
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2214
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.438
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0510
_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)+(0.0959P)²+1.4800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1438
_reflns_number_gt                1837
_reflns_number_total             2327
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2185.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               2225095
_cod_database_fobs_code          2225095
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.8592(4) 0.4740(4) 0.02573(6) 0.0412(8) Uani d . 1 . .
H H1A 0.9682 0.5407 0.0224 0.049 Uiso calc R 1 . .
H H1B 0.8078 0.4188 0.0126 0.049 Uiso calc R 1 . .
C C2 0.7901(4) 0.5749(4) 0.03281(5) 0.0336(7) Uani d . 1 . .
H H2A 0.8615 0.6547 0.0427 0.040 Uiso calc R 1 . .
H H2B 0.7778 0.6258 0.0202 0.040 Uiso calc R 1 . .
C C3 0.5888(4) 0.5827(4) 0.05172(5) 0.0379(8) Uani d . 1 . .
H H3A 0.6568 0.6427 0.0635 0.045 Uiso calc R 1 . .
H H3B 0.4873 0.5155 0.0580 0.045 Uiso calc R 1 . .
C C4 0.5751(4) 0.6906(4) 0.03705(5) 0.0360(7) Uani d . 1 . .
C C5 0.4092(4) 0.2743(4) 0.09939(5) 0.0394(8) Uani d . 1 . .
C C6 0.3004(4) 0.2578(4) 0.11629(5) 0.0389(8) Uani d . 1 . .
H H6A 0.1959 0.2111 0.1105 0.047 Uiso calc R 1 . .
H H6B 0.3281 0.3578 0.1225 0.047 Uiso calc R 1 . .
C C7 0.3123(5) 0.1525(4) 0.13332(5) 0.0404(8) Uani d . 1 . .
H H7A 0.3651 0.1029 0.1272 0.061 Uiso calc R 1 . .
H H7B 0.2101 0.0751 0.1378 0.061 Uiso calc R 1 . .
H H7C 0.3691 0.2133 0.1456 0.061 Uiso calc R 1 . .
Cl Cl1 1.0000 1.0000 0.07171(2) 0.0373(3) Uani d S 1 . .
Cl Cl2 0.3333 0.6667 0.09665(2) 0.0383(3) Uani d S 1 . .
Cu Cu1 0.6667 0.3333 0.063982(10) 0.0316(2) Uani d S 1 . .
N N1 0.6443(3) 0.4868(3) 0.04321(4) 0.0335(6) Uani d . 1 . .
N N2 0.5838(3) 0.7880(3) 0.02473(4) 0.0385(7) Uani d . 1 . .
N N3 0.4964(4) 0.3039(3) 0.08486(5) 0.0423(7) Uani d . 1 . .
O O1 0.3333 0.6667 0.1667 0.0247(10) Uani d S 1 . .
H H1C 0.3300 0.6081 0.1769 0.037 Uiso d PR 0.16667 . .
H H1D 0.3867 0.7608 0.1706 0.037 Uiso d PR 0.16667 . .
O O2 0.6667 0.3333 0.14060(6) 0.0353(8) Uani d S 1 . .
H H2C 0.6152 0.3741 0.1454 0.042 Uiso d PR 0.33333 . .
H H2D 0.6160 0.2696 0.1305 0.042 Uiso d PR 0.33333 . .
O O3 1.0000 1.0000 0.0000 0.0544(16) Uani d S 1 . .
H H3D 1.0241 1.0481 0.0120 0.065 Uiso d PR 0.16667 . .
H H3C 0.9020 0.9506 -0.0014 0.082 Uiso d PR 0.16667 . .
O O11 0.8501(3) 0.9383(3) 0.06411(4) 0.0473(7) Uani d . 1 . .
O O12 1.0000 1.0000 0.09409(6) 0.0442(10) Uani d S 1 . .
O O21 0.3333 0.6667 0.07487(7) 0.0413(10) Uani d S 1 . .
O O22 0.3579(3) 0.8074(3) 0.10312(4) 0.0379(5) Uani d . 1 . .
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 N1 . 3_665 112.9(3) ?
C2 C1 H1A . . 109.0 ?
N1 C1 H1A 3_665 . 109.0 ?
C2 C1 H1B . . 109.0 ?
N1 C1 H1B 3_665 . 109.0 ?
H1A C1 H1B . . 107.8 ?
N1 C2 C1 . . 112.2(3) ?
N1 C2 H2A . . 109.2 ?
C1 C2 H2A . . 109.2 ?
N1 C2 H2B . . 109.2 ?
C1 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
N1 C3 C4 . . 118.5(3) ?
N1 C3 H3A . . 107.7 ?
C4 C3 H3A . . 107.7 ?
N1 C3 H3B . . 107.7 ?
C4 C3 H3B . . 107.7 ?
H3A C3 H3B . . 107.1 ?
N2 C4 C3 . . 171.7(4) ?
N3 C5 C6 . . 171.5(4) ?
C5 C6 C7 . . 105.1(3) ?
C5 C6 H6A . . 110.7 ?
C7 C6 H6A . . 110.7 ?
C5 C6 H6B . . 110.7 ?
C7 C6 H6B . . 110.7 ?
H6A C6 H6B . . 108.8 ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O12 Cl1 O11 . 2_765 109.83(11) ?
O12 Cl1 O11 . . 109.83(11) ?
O11 Cl1 O11 2_765 . 109.11(11) ?
O12 Cl1 O11 . 3_675 109.83(11) ?
O11 Cl1 O11 2_765 3_675 109.11(11) ?
O11 Cl1 O11 . 3_675 109.11(11) ?
O21 Cl2 O22 . . 107.08(11) ?
O21 Cl2 O22 . 2_665 107.08(11) ?
O22 Cl2 O22 . 2_665 111.75(10) ?
O21 Cl2 O22 . 3_565 107.08(11) ?
O22 Cl2 O22 . 3_565 111.75(10) ?
O22 Cl2 O22 2_665 3_565 111.75(10) ?
N3 Cu1 N3 2_655 3_665 84.13(13) ?
N3 Cu1 N3 2_655 . 84.13(13) ?
N3 Cu1 N3 3_665 . 84.13(13) ?
N3 Cu1 N1 2_655 2_655 96.12(11) ?
N3 Cu1 N1 3_665 2_655 177.46(11) ?
N3 Cu1 N1 . 2_655 93.37(12) ?
N3 Cu1 N1 2_655 3_665 93.37(12) ?
N3 Cu1 N1 3_665 3_665 96.12(11) ?
N3 Cu1 N1 . 3_665 177.46(11) ?
N1 Cu1 N1 2_655 3_665 86.40(11) ?
N3 Cu1 N1 2_655 . 177.46(11) ?
N3 Cu1 N1 3_665 . 93.37(12) ?
N3 Cu1 N1 . . 96.12(11) ?
N1 Cu1 N1 2_655 . 86.40(11) ?
N1 Cu1 N1 3_665 . 86.40(11) ?
C2 N1 C3 . . 111.9(2) ?
C2 N1 C1 . 2_655 107.5(2) ?
C3 N1 C1 . 2_655 105.8(3) ?
C2 N1 Cu1 . . 106.2(2) ?
C3 N1 Cu1 . . 119.0(2) ?
C1 N1 Cu1 2_655 . 105.87(19) ?
C5 N3 Cu1 . . 167.5(3) ?
H1C O1 H1D . . 109.4 ?
H2C O2 H2D . . 109.5 ?
H3D O3 H3C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.538(5) ?
C1 N1 3_665 1.543(4) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 N1 . 1.420(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 N1 . 1.422(5) ?
C3 C4 . 1.462(5) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 N2 . 1.200(5) ?
C5 N3 . 1.178(5) ?
C5 C6 . 1.452(5) ?
C6 C7 . 1.529(4) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
Cl1 O12 . 1.379(4) ?
Cl1 O11 2_765 1.382(3) ?
Cl1 O11 . 1.382(3) ?
Cl1 O11 3_675 1.382(3) ?
Cl2 O21 . 1.342(4) ?
Cl2 O22 . 1.357(3) ?
Cl2 O22 2_665 1.357(3) ?
Cl2 O22 3_565 1.357(3) ?
Cu1 N3 2_655 2.030(3) ?
Cu1 N3 3_665 2.030(3) ?
Cu1 N3 . 2.030(3) ?
Cu1 N1 2_655 2.089(3) ?
Cu1 N1 3_665 2.089(3) ?
Cu1 N1 . 2.089(3) ?
N1 C1 2_655 1.543(4) ?
O1 H1C . 0.8500 ?
O1 H1D . 0.8500 ?
O2 H2C . 0.8500 ?
O2 H2D . 0.8500 ?
O3 H3D . 0.8500 ?
O3 H3C . 0.8500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1 H1A N2 2_765 0.97 2.49 3.371(5) 151
C3 H3A O11 . 0.97 2.59 3.269(4) 127
C6 H6A O12 1_445 0.97 2.27 3.120(4) 146
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 N1 3_665 . . . -43.3(4) ?
C1 C2 N1 C3 . . . . 173.9(3) ?
C1 C2 N1 C1 . . . 2_655 -70.5(4) ?
C1 C2 N1 Cu1 . . . . 42.5(3) ?
C4 C3 N1 C2 . . . . 54.9(4) ?
C4 C3 N1 C1 . . . 2_655 -61.8(3) ?
C4 C3 N1 Cu1 . . . . 179.4(2) ?
N3 Cu1 N1 C2 3_665 . . . 71.0(2) ?
N3 Cu1 N1 C2 . . . . 155.4(2) ?
N1 Cu1 N1 C2 2_655 . . . -111.58(15) ?
N1 Cu1 N1 C2 3_665 . . . -25.0(2) ?
N3 Cu1 N1 C3 3_665 . . . -56.3(2) ?
N3 Cu1 N1 C3 . . . . 28.2(2) ?
N1 Cu1 N1 C3 2_655 . . . 121.2(3) ?
N1 Cu1 N1 C3 3_665 . . . -152.2(3) ?
N3 Cu1 N1 C1 3_665 . . 2_655 -175.0(2) ?
N3 Cu1 N1 C1 . . . 2_655 -90.6(2) ?
N1 Cu1 N1 C1 2_655 . . 2_655 2.44(19) ?
N1 Cu1 N1 C1 3_665 . . 2_655 89.05(15) ?
N3 Cu1 N3 C5 2_655 . . . 10.1(14) ?
N3 Cu1 N3 C5 3_665 . . . -74.6(13) ?
N1 Cu1 N3 C5 2_655 . . . 105.9(14) ?
N1 Cu1 N3 C5 . . . . -167.3(14) ?
