#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:26:29 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180039 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/33/7033346.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_7033346
loop_
_publ_author_name
'Medina-Molner, Alfredo'
'Rohner, Melanie'
'Pandiarajan, Devaraj'
'Spingler, Bernhard'
_publ_section_title
;
 Mono- and dinuclear metal complexes containing the
 1,5,9-triazacyclododecane ([12]aneN3) unit and their interaction with
 DNA.
;
_journal_issue                   8
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3664
_journal_page_last               3672
_journal_paper_doi               10.1039/c4dt02713b
_journal_volume                  44
_journal_year                    2015
_chemical_formula_sum            'C28 H60 N6 Ni2 O10'
_chemical_formula_weight         758.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-08-28 deposited with the CCDC.
2014-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                102.060(18)
_cell_angle_beta                 105.113(18)
_cell_angle_gamma                94.828(18)
_cell_formula_units_Z            1
_cell_length_a                   8.6958(13)
_cell_length_b                   8.7403(13)
_cell_length_c                   12.3998(19)
_cell_measurement_reflns_used    7998
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      30.4
_cell_measurement_theta_min      3.2
_cell_volume                     880.1(3)
_computing_cell_refinement       'IPDS (Stoe, 1999)'
_computing_data_collection       'IPDS (Stoe, 1999)'
_computing_data_reduction        'X-RED (Stoe, 1999)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.905
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'φ oscillation 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  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15881
_diffrn_reflns_theta_full        30.42
_diffrn_reflns_theta_max         30.42
_diffrn_reflns_theta_min         3.40
_diffrn_standards_interval_count 'every image'
_diffrn_standards_interval_time  8
_diffrn_standards_number         50-200
_exptl_absorpt_coefficient_mu    1.130
_exptl_absorpt_correction_T_max  0.8433
_exptl_absorpt_correction_T_min  0.7265
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(Coppens et al., 1965)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             406
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0725P)²+0.2519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                4373
_reflns_number_total             4836
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4dt02713b2.cif
_cod_data_source_block           am050406
_cod_depositor_comments
'Adding full bibliography for 7033345--7033348.cif.'
_cod_original_cell_volume        880.1(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7033346
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Ni1 Ni 0.00373(2) 0.16065(2) 0.784761(16) 0.01956(8) Uani 1 1 d .
C1 C 0.1179(2) -0.1373(2) 0.84169(14) 0.0251(3) Uani 1 1 d .
H1A H 0.0025 -0.1826 0.8154 0.030 Uiso 1 1 calc R
H1B H 0.1734 -0.1939 0.8984 0.030 Uiso 1 1 calc R
C2 C 0.1857(2) -0.1700(2) 0.73818(15) 0.0264(3) Uani 1 1 d .
H2A H 0.2977 -0.1146 0.7622 0.032 Uiso 1 1 calc R
H2B H 0.1898 -0.2848 0.7159 0.032 Uiso 1 1 calc R
C3 C 0.0911(2) -0.1193(2) 0.63240(14) 0.0254(3) Uani 1 1 d .
H3A H 0.1357 -0.1578 0.5677 0.030 Uiso 1 1 calc R
H3B H -0.0224 -0.1702 0.6102 0.030 Uiso 1 1 calc R
C4 C 0.2427(2) 0.1309(2) 0.63265(15) 0.0281(3) Uani 1 1 d .
H4A H 0.2394 0.0941 0.5508 0.034 Uiso 1 1 calc R
H4B H 0.3380 0.0965 0.6797 0.034 Uiso 1 1 calc R
C5 C 0.2620(2) 0.3108(2) 0.66394(16) 0.0314(4) Uani 1 1 d .
H5A H 0.1579 0.3442 0.6298 0.038 Uiso 1 1 calc R
H5B H 0.3420 0.3524 0.6293 0.038 Uiso 1 1 calc R
C6 C 0.3159(2) 0.3849(3) 0.79393(17) 0.0331(4) Uani 1 1 d .
H6A H 0.4104 0.3388 0.8302 0.040 Uiso 1 1 calc R
H6B H 0.3497 0.5000 0.8072 0.040 Uiso 1 1 calc R
C7 C 0.2526(2) 0.3919(2) 0.97708(15) 0.0304(4) Uani 1 1 d .
H7B H 0.1620 0.3946 1.0116 0.036 Uiso 1 1 calc R
H7A H 0.3197 0.4973 1.0060 0.036 Uiso 1 1 calc R
C8 C 0.3545(2) 0.2675(3) 1.01606(15) 0.0308(4) Uani 1 1 d .
H8A H 0.4681 0.3041 1.0226 0.037 Uiso 1 1 calc R
H8B H 0.3486 0.2624 1.0939 0.037 Uiso 1 1 calc R
C9 C 0.3074(2) 0.1006(2) 0.93876(15) 0.0268(3) Uani 1 1 d .
H9A H 0.3425 0.1000 0.8689 0.032 Uiso 1 1 calc R
H9B H 0.3685 0.0289 0.9797 0.032 Uiso 1 1 calc R
C10 C 0.08354(19) 0.0436(2) 1.01029(14) 0.0231(3) Uani 1 1 d .
H10A H 0.0869 0.1563 1.0473 0.028 Uiso 1 1 calc R
H10B H 0.1622 -0.0008 1.0642 0.028 Uiso 1 1 calc R
C20 C -0.3344(2) -0.0221(2) 0.70994(15) 0.0265(3) Uani 1 1 d .
C21 C -0.4532(2) -0.1532(3) 0.6194(2) 0.0436(5) Uani 1 1 d .
H21A H -0.4856 -0.2350 0.6557 0.065 Uiso 1 1 calc R
H21B H -0.4025 -0.1995 0.5608 0.065 Uiso 1 1 calc R
H21C H -0.5484 -0.1097 0.5833 0.065 Uiso 1 1 calc R
C30 C -0.1494(2) 0.4185(2) 0.68200(17) 0.0318(4) Uani 1 1 d .
C31 C -0.2245(4) 0.4835(3) 0.5799(2) 0.0535(7) Uani 1 1 d .
H31A H -0.3407 0.4466 0.5530 0.080 Uiso 1 1 calc R
H31B H -0.1762 0.4465 0.5178 0.080 Uiso 1 1 calc R
H31C H -0.2052 0.5993 0.6026 0.080 Uiso 1 1 calc R
N1 N 0.13327(16) 0.03371(18) 0.90173(11) 0.0206(3) Uani 1 1 d .
N2 N 0.09490(16) 0.05471(18) 0.65077(12) 0.0215(3) Uani 1 1 d .
H2 H 0.0157 0.0624 0.5861 0.026 Uiso 1 1 calc R
N3 N 0.18746(19) 0.3599(2) 0.85015(13) 0.0270(3) Uani 1 1 d .
H3 H 0.1306 0.4439 0.8402 0.032 Uiso 1 1 calc R
O1 O -0.12218(17) 0.27404(18) 0.89519(11) 0.0273(3) Uani 1 1 d .
H33 H -0.124(4) 0.358(5) 0.871(3) 0.063(10) Uiso 1 1 d .
H32 H -0.208(4) 0.216(5) 0.863(3) 0.063(10) Uiso 1 1 d .
O20 O -0.18858(15) -0.01884(16) 0.70939(11) 0.0258(3) Uani 1 1 d .
O21 O -0.38666(16) 0.0717(2) 0.77885(13) 0.0358(3) Uani 1 1 d .
O30 O -0.11530(17) 0.27913(17) 0.66072(11) 0.0282(3) Uani 1 1 d .
O31 O -0.1225(2) 0.50679(19) 0.78115(14) 0.0451(4) 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 0.0033 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O20 Ni1 N2 84.74(6) . .
O20 Ni1 O1 90.47(6) . .
N2 Ni1 O1 169.59(5) . .
O20 Ni1 N3 173.66(5) . .
N2 Ni1 N3 95.13(6) . .
O1 Ni1 N3 88.60(6) . .
O20 Ni1 O30 85.72(6) . .
N2 Ni1 O30 82.83(5) . .
O1 Ni1 O30 87.60(5) . .
N3 Ni1 O30 87.98(6) . .
O20 Ni1 N1 94.39(6) . .
N2 Ni1 N1 93.09(5) . .
O1 Ni1 N1 96.50(5) . .
N3 Ni1 N1 91.94(6) . .
O30 Ni1 N1 175.90(5) . .
N1 C1 C2 115.76(14) . .
N1 C1 H1A 108.3 . .
C2 C1 H1A 108.3 . .
N1 C1 H1B 108.3 . .
C2 C1 H1B 108.3 . .
H1A C1 H1B 107.4 . .
C3 C2 C1 115.19(13) . .
C3 C2 H2A 108.5 . .
C1 C2 H2A 108.5 . .
C3 C2 H2B 108.5 . .
C1 C2 H2B 108.5 . .
H2A C2 H2B 107.5 . .
N2 C3 C2 113.54(14) . .
N2 C3 H3A 108.9 . .
C2 C3 H3A 108.9 . .
N2 C3 H3B 108.9 . .
C2 C3 H3B 108.9 . .
H3A C3 H3B 107.7 . .
N2 C4 C5 113.27(14) . .
N2 C4 H4A 108.9 . .
C5 C4 H4A 108.9 . .
N2 C4 H4B 108.9 . .
C5 C4 H4B 108.9 . .
H4A C4 H4B 107.7 . .
C4 C5 C6 114.03(16) . .
C4 C5 H5A 108.7 . .
C6 C5 H5A 108.7 . .
C4 C5 H5B 108.7 . .
C6 C5 H5B 108.7 . .
H5A C5 H5B 107.6 . .
N3 C6 C5 113.02(16) . .
N3 C6 H6A 109.0 . .
C5 C6 H6A 109.0 . .
N3 C6 H6B 109.0 . .
C5 C6 H6B 109.0 . .
H6A C6 H6B 107.8 . .
N3 C7 C8 112.85(15) . .
N3 C7 H7B 109.0 . .
C8 C7 H7B 109.0 . .
N3 C7 H7A 109.0 . .
C8 C7 H7A 109.0 . .
H7B C7 H7A 107.8 . .
C9 C8 C7 116.21(15) . .
C9 C8 H8A 108.2 . .
C7 C8 H8A 108.2 . .
C9 C8 H8B 108.2 . .
C7 C8 H8B 108.2 . .
H8A C8 H8B 107.4 . .
N1 C9 C8 116.71(14) . .
N1 C9 H9A 108.1 . .
C8 C9 H9A 108.1 . .
N1 C9 H9B 108.1 . .
C8 C9 H9B 108.1 . .
H9A C9 H9B 107.3 . .
N1 C10 C10 113.28(17) . 2_557
N1 C10 H10A 108.9 . .
C10 C10 H10A 108.9 2_557 .
N1 C10 H10B 108.9 . .
C10 C10 H10B 108.9 2_557 .
H10A C10 H10B 107.7 . .
O21 C20 O20 125.81(18) . .
O21 C20 C21 118.40(16) . .
O20 C20 C21 115.78(16) . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
O31 C30 O30 124.90(18) . .
O31 C30 C31 118.09(19) . .
O30 C30 C31 117.00(19) . .
C30 C31 H31A 109.5 . .
C30 C31 H31B 109.5 . .
H31A C31 H31B 109.5 . .
C30 C31 H31C 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
C9 N1 C1 107.57(13) . .
C9 N1 C10 106.26(13) . .
C1 N1 C10 108.86(13) . .
C9 N1 Ni1 108.74(10) . .
C1 N1 Ni1 110.02(10) . .
C10 N1 Ni1 115.08(10) . .
C3 N2 C4 111.29(13) . .
C3 N2 Ni1 115.01(10) . .
C4 N2 Ni1 121.26(11) . .
C3 N2 H2 101.9 . .
C4 N2 H2 101.9 . .
Ni1 N2 H2 101.9 . .
C7 N3 C6 112.01(15) . .
C7 N3 Ni1 111.45(12) . .
C6 N3 Ni1 122.10(13) . .
C7 N3 H3 102.8 . .
C6 N3 H3 102.8 . .
Ni1 N3 H3 102.8 . .
Ni1 O1 H33 96(2) . .
Ni1 O1 H32 96(2) . .
H33 O1 H32 109(3) . .
C20 O20 Ni1 129.87(13) . .
C30 O30 Ni1 125.88(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O20 2.0644(15) .
Ni1 N2 2.1009(14) .
Ni1 O1 2.1102(13) .
Ni1 N3 2.1235(17) .
Ni1 O30 2.1272(13) .
Ni1 N1 2.1528(14) .
C1 N1 1.502(2) .
C1 C2 1.532(2) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C3 1.528(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 N2 1.486(2) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 N2 1.488(2) .
C4 C5 1.523(3) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.535(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 N3 1.486(2) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 N3 1.484(2) .
C7 C8 1.536(3) .
C7 H7B 0.9900 .
C7 H7A 0.9900 .
C8 C9 1.525(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 N1 1.491(2) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 N1 1.5058(19) .
C10 C10 1.515(3) 2_557
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C20 O21 1.257(2) .
C20 O20 1.268(2) .
C20 C21 1.516(3) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C30 O31 1.259(3) .
C30 O30 1.269(2) .
C30 C31 1.511(3) .
C31 H31A 0.9800 .
C31 H31B 0.9800 .
C31 H31C 0.9800 .
N2 H2 0.9300 .
N3 H3 0.9300 .
O1 H33 0.85(4) .
O1 H32 0.81(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
N3 H3 O31 0.93 2.28 3.080(2) 143.3
O1 H33 O31 0.85(4) 1.88(4) 2.709(2) 164(3)
O1 H32 O21 0.81(4) 1.84(4) 2.649(2) 172(4)
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
_geom_torsion_site_symmetry_1
N1 C1 C2 C3 -69.8(2) .
C1 C2 C3 N2 65.9(2) .
N2 C4 C5 C6 74.9(2) .
C4 C5 C6 N3 -71.7(2) .
N3 C7 C8 C9 -30.5(2) .
C7 C8 C9 N1 -48.1(2) .
C8 C9 N1 C1 -171.94(14) .
C8 C9 N1 C10 -55.48(18) .
C8 C9 N1 Ni1 68.94(16) .
C2 C1 N1 C9 -57.13(17) .
C2 C1 N1 C10 -171.88(14) .
C2 C1 N1 Ni1 61.16(16) .
C10 C10 N1 C9 -170.62(17) 2_557
C10 C10 N1 C1 -55.0(2) 2_557
C10 C10 N1 Ni1 69.0(2) 2_557
O20 Ni1 N1 C9 157.61(11) .
N2 Ni1 N1 C9 72.65(11) .
O1 Ni1 N1 C9 -111.41(11) .
N3 Ni1 N1 C9 -22.59(11) .
O30 Ni1 N1 C9 66.2(7) .
O20 Ni1 N1 C1 40.04(11) .
N2 Ni1 N1 C1 -44.92(11) .
O1 Ni1 N1 C1 131.02(10) .
N3 Ni1 N1 C1 -140.17(11) .
O30 Ni1 N1 C1 -51.3(7) .
O20 Ni1 N1 C10 -83.36(12) .
N2 Ni1 N1 C10 -168.31(12) .
O1 Ni1 N1 C10 7.62(12) .
N3 Ni1 N1 C10 96.44(12) .
O30 Ni1 N1 C10 -174.7(7) .
C2 C3 N2 C4 83.92(16) .
C2 C3 N2 Ni1 -58.87(16) .
C5 C4 N2 C3 -173.30(14) .
C5 C4 N2 Ni1 -33.18(18) .
O20 Ni1 N2 C3 -48.40(11) .
O1 Ni1 N2 C3 -111.3(3) .
N3 Ni1 N2 C3 137.96(11) .
O30 Ni1 N2 C3 -134.73(12) .
N1 Ni1 N2 C3 45.73(11) .
O20 Ni1 N2 C4 172.85(12) .
O1 Ni1 N2 C4 109.9(3) .
N3 Ni1 N2 C4 -0.79(13) .
O30 Ni1 N2 C4 86.52(13) .
N1 Ni1 N2 C4 -93.02(12) .
C8 C7 N3 C6 -69.8(2) .
C8 C7 N3 Ni1 70.93(17) .
C5 C6 N3 C7 164.25(17) .
C5 C6 N3 Ni1 28.3(2) .
O20 Ni1 N3 C7 138.3(4) .
N2 Ni1 N3 C7 -133.12(12) .
O1 Ni1 N3 C7 56.61(12) .
O30 Ni1 N3 C7 144.26(12) .
N1 Ni1 N3 C7 -39.84(12) .
O20 Ni1 N3 C6 -85.5(5) .
N2 Ni1 N3 C6 3.08(15) .
O1 Ni1 N3 C6 -167.18(14) .
O30 Ni1 N3 C6 -79.53(14) .
N1 Ni1 N3 C6 96.36(14) .
O21 C20 O20 Ni1 -17.6(3) .
C21 C20 O20 Ni1 163.24(16) .
N2 Ni1 O20 C20 -152.34(16) .
O1 Ni1 O20 C20 18.40(16) .
N3 Ni1 O20 C20 -63.2(5) .
O30 Ni1 O20 C20 -69.16(16) .
N1 Ni1 O20 C20 114.95(16) .
O31 C30 O30 Ni1 -2.6(3) .
C31 C30 O30 Ni1 176.00(17) .
O20 Ni1 O30 C30 127.14(17) .
N2 Ni1 O30 C30 -147.63(17) .
O1 Ni1 O30 C30 36.48(17) .
N3 Ni1 O30 C30 -52.20(17) .
N1 Ni1 O30 C30 -141.2(7) .
