#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:33:36 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179976 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/70/7027071.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_7027071
loop_
_publ_author_name
'Weyhermüller, Thomas'
'Weighardt, Karl'
'Chaudhuri, Phalguni'
_publ_section_title
;
 Nitrogen versus oxygen co-ordination of carboxamide-functionalized
 triazacyclononane ligands in transition metal ion complexes
;
_journal_issue                   22
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              3805
_journal_paper_doi               10.1039/a806466k
_journal_year                    1998
_chemical_formula_structural     '[C12 H24 N6 Ni O3]2+, 2 (ClO4)-'
_chemical_formula_sum            'C12 H24 Cl2 N6 Ni O11'
_chemical_formula_weight         557.98
_chemical_name_systematic
; 
 ? 
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 106.43(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.034(1)
_cell_length_b                   11.874(1)
_cell_length_c                   10.573(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.95
_cell_measurement_theta_min      18.45
_cell_volume                     2171.6(5)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Nonius CAD4'
_diffrn_measurement_method       2θ/ω-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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0645
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4541
_diffrn_reflns_theta_max         26.29
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.207
_exptl_absorpt_correction_type   'not measured'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_description       'transparent block'
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          1.12
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.928
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.042
_refine_ls_goodness_of_fit_obs   1.091
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_restrained_S_obs      1.091
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_obs          0.0662
_refine_ls_shift/esd_max         0.006
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1160P)²+3.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2126
_refine_ls_wR_factor_obs         0.1768
_reflns_number_observed          2799
_reflns_number_total             4306
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            806466Ksup1.cif
_cod_data_source_block           9
_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 2.4.2 from 2011-04-26.

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

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1160P)^2^+3.5000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1160P)^2^+3.5000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7027071
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
Ni Ni 0.25103(4) 0.60639(5) 0.31636(6) 0.0409(3) Uani 1 d .
O1 O 0.2637(2) 0.6268(3) 0.5135(4) 0.0473(9) Uani 1 d .
O2 O 0.1510(3) 0.6942(4) 0.2535(5) 0.0757(15) Uani 1 d .
O3 O 0.3150(2) 0.7502(3) 0.3099(4) 0.0490(9) Uani 1 d .
N1 N 0.2124(3) 0.4495(4) 0.3550(4) 0.0476(11) Uani 1 d .
N2 N 0.2227(5) 0.5558(5) 0.1231(6) 0.080(2) Uani 1 d .
N3 N 0.3558(3) 0.5312(4) 0.3349(5) 0.0588(13) Uani 1 d .
N4 N 0.2283(4) 0.5520(5) 0.6823(6) 0.064(2) Uani 1 d .
H4C H 0.1831(51) 0.5666(75) 0.6535(88) 0.083 Uiso 1 d .
H4D H 0.2475(49) 0.6089(68) 0.7280(89) 0.083 Uiso 1 d .
N5 N 0.0674(4) 0.7683(9) 0.0730(10) 0.148(5) Uani 1 d .
N6 N 0.4363(5) 0.8120(7) 0.3560(11) 0.110(3) Uani 1 d .
H6C H 0.4150(72) 0.8764(104) 0.3383(136) 0.143 Uiso 1 d .
H6D H 0.4889(67) 0.8141(102) 0.3839(115) 0.143 Uiso 1 d .
C1 C 0.1540(5) 0.4203(6) 0.2306(7) 0.077(2) Uani 1 d .
H1A H 0.1083(5) 0.4664(6) 0.2202(7) 0.092 Uiso 1 calc R
H1B H 0.1392(5) 0.3419(6) 0.2327(7) 0.092 Uiso 1 calc R
C2 C 0.1874(7) 0.4398(7) 0.1141(7) 0.099(3) Uani 1 d .
H2A H 0.2265(7) 0.3834(7) 0.1150(7) 0.119 Uiso 1 calc R
H2B H 0.1467(7) 0.4325(7) 0.0319(7) 0.119 Uiso 1 calc R
C3 C 0.2990(7) 0.5529(7) 0.0941(8) 0.101(3) Uani 1 d .
H3A H 0.3159(7) 0.6293(7) 0.0853(8) 0.122 Uiso 1 calc R
H3B H 0.2934(7) 0.5143(7) 0.0111(8) 0.122 Uiso 1 calc R
C4 C 0.3589(6) 0.4937(7) 0.2017(9) 0.091(3) Uani 1 d .
H4A H 0.3503(6) 0.4130(7) 0.1935(9) 0.110 Uiso 1 calc R
H4B H 0.4098(6) 0.5091(7) 0.1921(9) 0.110 Uiso 1 calc R
C5 C 0.3560(4) 0.4347(6) 0.4253(8) 0.068(2) Uani 1 d .
H5A H 0.3659(4) 0.4624(6) 0.5149(8) 0.081 Uiso 1 calc R
H5B H 0.3972(4) 0.3830(6) 0.4229(8) 0.081 Uiso 1 calc R
C6 C 0.2802(4) 0.3731(5) 0.3870(7) 0.062(2) Uani 1 d .
H6A H 0.2779(4) 0.3261(5) 0.3110(7) 0.075 Uiso 1 calc R
H6B H 0.2774(4) 0.3241(5) 0.4590(7) 0.075 Uiso 1 calc R
C7 C 0.1809(4) 0.4646(5) 0.4661(6) 0.0538(15) Uani 1 d .
H7A H 0.1827(4) 0.3938(5) 0.5127(6) 0.065 Uiso 1 calc R
H7B H 0.1273(4) 0.4884(5) 0.4347(6) 0.065 Uiso 1 calc R
C8 C 0.2285(4) 0.5541(5) 0.5597(6) 0.0480(13) Uani 1 d .
C9 C 0.1695(7) 0.6408(8) 0.0448(8) 0.109(4) Uani 1 d .
H9A H 0.1323(7) 0.6045(8) -0.0283(8) 0.131 Uiso 1 calc R
H9B H 0.1985(7) 0.6950(8) 0.0090(8) 0.131 Uiso 1 calc R
C10 C 0.1274(5) 0.7012(8) 0.1316(10) 0.096(3) Uani 1 d .
C11 C 0.4147(4) 0.6153(6) 0.3929(8) 0.069(2) Uani 1 d .
H11A H 0.4611(4) 0.6002(6) 0.3666(8) 0.083 Uiso 1 calc R
H11B H 0.4278(4) 0.6112(6) 0.4883(8) 0.083 Uiso 1 calc R
C12 C 0.3848(4) 0.7320(5) 0.3475(7) 0.058(2) Uani 1 d .
Cl1 Cl 0.41153(11) 0.14056(14) 0.3073(2) 0.0641(5) Uani 1 d .
O11 O 0.4703(6) 0.2186(8) 0.3207(10) 0.165(4) Uani 1 d .
O12 O 0.3941(5) 0.1331(8) 0.4241(8) 0.140(3) Uani 1 d .
O13 O 0.3488(6) 0.1887(6) 0.2079(7) 0.148(4) Uani 1 d .
O14 O 0.4349(5) 0.0395(5) 0.2605(8) 0.117(2) Uani 1 d .
Cl2 Cl 0.05979(11) 0.1061(2) 0.2439(2) 0.0679(5) Uani 1 d .
O21 O 0.0329(5) 0.0433(10) 0.3288(12) 0.207(6) Uani 1 d .
O22 O 0.0223(5) 0.2068(8) 0.2248(13) 0.182(5) Uani 1 d .
O23 O 0.0387(8) 0.0554(16) 0.1229(11) 0.274(9) Uani 1 d .
O24 O 0.1401(4) 0.1141(5) 0.2856(6) 0.092(2) Uani 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'
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'
Ni Ni 0.3393 1.1124 '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
O2 Ni O1 96.1(2)
O2 Ni N3 165.3(2)
O1 Ni N3 96.9(2)
O2 Ni N2 82.9(3)
O1 Ni N2 167.0(2)
N3 Ni N2 86.0(3)
O2 Ni N1 102.1(2)
O1 Ni N1 81.5(2)
N3 Ni N1 86.6(2)
N2 Ni N1 86.0(2)
O2 Ni O3 91.0(2)
O1 Ni O3 91.9(2)
N3 Ni O3 81.7(2)
N2 Ni O3 101.1(2)
N1 Ni O3 165.8(2)
C8 O1 Ni 113.1(4)
C10 O2 Ni 112.8(6)
C12 O3 Ni 111.9(4)
C7 N1 C1 113.9(6)
C7 N1 C6 112.2(5)
C1 N1 C6 113.2(5)
C7 N1 Ni 106.2(3)
C1 N1 Ni 103.3(4)
C6 N1 Ni 107.1(4)
C9 N2 C3 113.0(7)
C9 N2 C2 113.2(7)
C3 N2 C2 111.3(8)
C9 N2 Ni 107.3(6)
C3 N2 Ni 103.2(5)
C2 N2 Ni 108.2(4)
C11 N3 C5 112.8(6)
C11 N3 C4 112.6(6)
C5 N3 C4 112.4(6)
C11 N3 Ni 106.4(4)
C5 N3 Ni 103.4(4)
C4 N3 Ni 108.6(5)
N1 C1 C2 109.7(7)
N2 C2 C1 110.0(6)
N2 C3 C4 111.2(6)
N3 C4 C3 111.3(7)
N3 C5 C6 111.4(6)
N1 C6 C5 113.1(5)
N1 C7 C8 109.3(5)
O1 C8 N4 123.3(6)
O1 C8 C7 118.6(5)
N4 C8 C7 118.1(6)
N2 C9 C10 109.9(7)
O2 C10 N5 120.9(12)
O2 C10 C9 120.7(8)
N5 C10 C9 118.3(9)
N3 C11 C12 110.0(6)
O3 C12 N6 122.4(7)
O3 C12 C11 120.3(6)
N6 C12 C11 117.3(7)
O12 Cl1 O11 108.5(6)
O12 Cl1 O14 115.6(5)
O11 Cl1 O14 108.0(5)
O12 Cl1 O13 110.9(5)
O11 Cl1 O13 103.4(7)
O14 Cl1 O13 109.6(5)
O21 Cl2 O22 109.0(7)
O21 Cl2 O23 108.7(11)
O22 Cl2 O23 104.7(8)
O21 Cl2 O24 111.2(5)
O22 Cl2 O24 114.6(5)
O23 Cl2 O24 108.3(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ni O2 2.026(5)
Ni O1 2.046(4)
Ni N3 2.049(5)
Ni N2 2.051(6)
Ni N1 2.070(5)
Ni O3 2.073(4)
O1 C8 1.250(7)
O2 C10 1.240(10)
O3 C12 1.227(8)
N1 C7 1.453(8)
N1 C1 1.475(8)
N1 C6 1.482(8)
N2 C9 1.476(12)
N2 C3 1.491(13)
N2 C2 1.509(9)
N3 C11 1.461(9)
N3 C5 1.492(8)
N3 C4 1.493(9)
N4 C8 1.298(8)
N5 C10 1.345(11)
N6 C12 1.314(9)
C1 C2 1.535(13)
C3 C4 1.504(13)
C5 C6 1.501(10)
C7 C8 1.538(8)
C9 C10 1.53(2)
C11 C12 1.514(9)
Cl1 O12 1.360(7)
Cl1 O11 1.385(8)
Cl1 O14 1.408(6)
Cl1 O13 1.428(7)
Cl2 O21 1.357(9)
Cl2 O22 1.360(9)
Cl2 O23 1.367(10)
Cl2 O24 1.393(6)
