#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:16:12 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179474 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/71/4337196.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_4337196
loop_
_publ_author_name
'Esteban, Jordi'
'Font-Bardia, Mercè'
'Escuer, Albert'
_publ_section_title
;
 Anionic guests in prismatic cavities generated by enneanuclear nickel
 metallacycles.
;
_journal_issue                   2
_journal_name_full               'Inorganic chemistry'
_journal_page_first              1113
_journal_page_last               1121
_journal_paper_doi               10.1021/ic402651k
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         'C108 H156 N57 Ni9 O6, 2(H2 O), 3(I)'
_chemical_formula_sum            'C108 H160 I3 N57 Ni9 O8'
_chemical_formula_weight         3294.02
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           167
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3 2"c'
_symmetry_space_group_name_H-M   'R -3 c :H'
_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                120.00
_cell_formula_units_Z            6
_cell_length_a                   17.9113(12)
_cell_length_b                   17.9113(12)
_cell_length_c                   72.574(5)
_cell_measurement_reflns_used    1995
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.34
_cell_measurement_theta_min      2.42
_cell_volume                     20163(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       90
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4598
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    1.995
_exptl_absorpt_correction_T_max  0.71
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             10092
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.153
_refine_diff_density_min         -2.239
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4598
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0545
_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)+(0.1108P)²+83.3892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1679
_refine_ls_wR_factor_ref         0.1883
_reflns_number_gt                3332
_reflns_number_total             4598
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic402651k_si_001.cif
_cod_data_source_block           af06fua1na
_cod_original_cell_volume        20164(2)
_cod_original_sg_symbol_H-M      R-3c
_cod_database_code               4337196
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'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'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'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'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-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'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-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'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
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 0.32550(4) 0.3333 0.0833 0.0245(2) Uani 1 2 d S
Ni2 Ni 0.51404(4) 0.47526(4) 0.058528(9) 0.0314(2) Uani 1 1 d .
I1 I 0.6667 0.3333 0.0833 0.0836(5) Uani 1 6 d S
I2 I 0.0000 0.0000 0.127771(13) 0.0716(3) Uani 1 3 d S
O1 O 0.3950(2) 0.4210(2) 0.04667(5) 0.0330(8) Uani 1 1 d .
N1 N 0.2009(2) 0.2440(2) 0.07568(5) 0.0282(8) Uani 1 1 d .
N2 N 0.3282(2) 0.3590(3) 0.05551(6) 0.0283(9) Uani 1 1 d .
N3 N 0.5142(3) 0.3607(3) 0.05631(6) 0.0347(10) Uani 1 1 d .
H3A H 0.5667 0.3706 0.0597 0.042 Uiso 1 1 calc R
H3B H 0.4762 0.3237 0.0645 0.042 Uiso 1 1 calc R
N4 N 0.5677(3) 0.5165(3) 0.03216(7) 0.0486(11) Uani 1 1 d U
H4O H 0.6240 0.5321 0.0340 0.058 Uiso 1 1 calc R
N5 N 0.5089(4) 0.5892(3) 0.06163(8) 0.0539(13) Uani 1 1 d .
H5A H 0.4581 0.5782 0.0568 0.065 Uiso 1 1 calc R
H5B H 0.5053 0.5959 0.0738 0.065 Uiso 1 1 calc R
N6 N 0.3589(3) 0.2352(3) 0.08126(5) 0.0298(9) Uani 1 1 d .
N7 N 0.3236(3) 0.1826(3) 0.06908(6) 0.0304(9) Uani 1 1 d .
N8 N 0.2889(3) 0.1322(3) 0.05743(7) 0.0422(11) Uani 1 1 d .
N9 N 0.6413(3) 0.5351(4) 0.06835(8) 0.0538(13) Uani 1 1 d .
N10 N 0.6667 0.5476(3) 0.0833 0.0362(14) Uani 1 2 d S
C1 C 0.1389(3) 0.1858(3) 0.08650(7) 0.0311(10) Uani 1 1 d .
H1 H 0.1515 0.1826 0.0988 0.037 Uiso 1 1 calc R
C2 C 0.0576(3) 0.1308(3) 0.08018(8) 0.0356(11) Uani 1 1 d .
H2 H 0.0161 0.0907 0.0881 0.043 Uiso 1 1 calc R
C3 C 0.0373(3) 0.1350(3) 0.06197(8) 0.0385(12) Uani 1 1 d .
H3 H -0.0181 0.0990 0.0575 0.046 Uiso 1 1 calc R
C4 C 0.1034(3) 0.1959(4) 0.05018(8) 0.0355(11) Uani 1 1 d .
H4 H 0.0924 0.2005 0.0378 0.043 Uiso 1 1 calc R
C5 C 0.1847(3) 0.2482(3) 0.05759(7) 0.0292(10) Uani 1 1 d .
C6 C 0.2576(3) 0.3120(3) 0.04655(6) 0.0285(10) Uani 1 1 d .
C7 C 0.2472(3) 0.3211(4) 0.02658(7) 0.0359(11) Uani 1 1 d .
C8 C 0.2250(4) 0.2533(4) 0.01510(8) 0.0520(15) Uani 1 1 d .
H8 H 0.2194 0.2019 0.0195 0.062 Uiso 1 1 calc R
C9 C 0.2102(5) 0.2631(6) -0.00453(11) 0.075(2) Uani 1 1 d U
H9 H 0.1949 0.2175 -0.0127 0.090 Uiso 1 1 calc R
C10 C 0.2185(5) 0.3358(6) -0.01048(11) 0.076(2) Uani 1 1 d U
H10 H 0.2052 0.3398 -0.0227 0.091 Uiso 1 1 calc R
C11 C 0.2465(5) 0.4072(5) 0.00095(10) 0.0643(19) Uani 1 1 d .
H11 H 0.2562 0.4594 -0.0039 0.077 Uiso 1 1 calc R
C12 C 0.2601(4) 0.4008(4) 0.01938(8) 0.0483(14) Uani 1 1 d .
H12 H 0.2775 0.4481 0.0271 0.058 Uiso 1 1 calc R
C13 C 0.4941(4) 0.3174(4) 0.03842(8) 0.0479(14) Uani 1 1 d .
H13A H 0.4354 0.3006 0.0350 0.058 Uiso 1 1 calc R
H13B H 0.4983 0.2656 0.0393 0.058 Uiso 1 1 calc R
C14 C 0.5556(4) 0.3761(4) 0.02363(9) 0.0555(16) Uani 1 1 d .
H14A H 0.5484 0.3425 0.0126 0.067 Uiso 1 1 calc R
H14B H 0.6144 0.3991 0.0279 0.067 Uiso 1 1 calc R
C15 C 0.5412(4) 0.4506(4) 0.01879(9) 0.0560(17) Uani 1 1 d .
H15A H 0.5716 0.4764 0.0074 0.067 Uiso 1 1 calc R
H15B H 0.4802 0.4274 0.0165 0.067 Uiso 1 1 calc R
C16 C 0.5740(6) 0.5992(5) 0.02582(11) 0.078(2) Uani 1 1 d U
H16A H 0.5162 0.5901 0.0244 0.094 Uiso 1 1 calc R
H16B H 0.6016 0.6140 0.0138 0.094 Uiso 1 1 calc R
C18 C 0.5736(6) 0.6745(5) 0.05455(11) 0.082(2) Uani 1 1 d D
H18A H 0.5443 0.7058 0.0512 0.098 Uiso 1 1 calc R
H18B H 0.6133 0.7062 0.0645 0.098 Uiso 1 1 calc R
C17 C 0.6234(6) 0.6740(5) 0.03873(11) 0.080(2) Uani 1 1 d D
H17A H 0.6738 0.6724 0.0431 0.096 Uiso 1 1 calc R
H17B H 0.6435 0.7273 0.0319 0.096 Uiso 1 1 calc R
O1W O 0.0000 0.0000 0.0050(7) 0.195(18) Uani 1 3 d S
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'
I I -0.4742 1.8119 '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
N2 Ni1 N2 169.9(2) 17_554 .
N2 Ni1 N1 78.81(15) 17_554 17_554
N2 Ni1 N1 94.16(15) . 17_554
N2 Ni1 N1 94.16(15) 17_554 .
N2 Ni1 N1 78.80(15) . .
N1 Ni1 N1 92.3(2) 17_554 .
N2 Ni1 N6 89.54(15) 17_554 .
N2 Ni1 N6 97.47(15) . .
N1 Ni1 N6 168.34(15) 17_554 .
N1 Ni1 N6 89.01(15) . .
N2 Ni1 N6 97.48(15) 17_554 17_554
N2 Ni1 N6 89.54(15) . 17_554
N1 Ni1 N6 89.01(15) 17_554 17_554
N1 Ni1 N6 168.33(15) . 17_554
N6 Ni1 N6 92.0(2) . 17_554
O1 Ni2 N3 90.85(15) . .
O1 Ni2 N9 174.79(18) . .
N3 Ni2 N9 89.6(2) . .
O1 Ni2 N5 87.95(19) . .
N3 Ni2 N5 177.32(19) . .
N9 Ni2 N5 91.8(2) . .
O1 Ni2 N4 88.22(17) . .
N3 Ni2 N4 92.88(19) . .
N9 Ni2 N4 86.6(2) . .
N5 Ni2 N4 89.5(2) . .
O1 Ni2 N6 90.92(14) . 17_554
N3 Ni2 N6 86.84(16) . 17_554
N9 Ni2 N6 94.28(19) . 17_554
N5 Ni2 N6 90.78(18) . 17_554
N4 Ni2 N6 179.10(19) . 17_554
N2 O1 Ni2 119.1(3) . .
C1 N1 C5 119.8(4) . .
C1 N1 Ni1 126.9(3) . .
C5 N1 Ni1 113.3(3) . .
C6 N2 O1 118.9(4) . .
C6 N2 Ni1 116.1(3) . .
O1 N2 Ni1 124.9(3) . .
C13 N3 Ni2 118.4(4) . .
C13 N3 H3A 107.7 . .
Ni2 N3 H3A 107.7 . .
C13 N3 H3B 107.7 . .
Ni2 N3 H3B 107.7 . .
H3A N3 H3B 107.1 . .
C15 N4 C16 116.2(6) . .
C15 N4 Ni2 115.3(4) . .
C16 N4 Ni2 114.9(4) . .
C15 N4 H4O 102.5 . .
C16 N4 H4O 102.5 . .
Ni2 N4 H4O 102.5 . .
C18 N5 Ni2 125.2(5) . .
C18 N5 H5A 106.0 . .
Ni2 N5 H5A 106.0 . .
C18 N5 H5B 106.0 . .
Ni2 N5 H5B 106.0 . .
H5A N5 H5B 106.3 . .
N7 N6 Ni1 116.1(3) . .
N7 N6 Ni2 119.0(3) . 17_554
Ni1 N6 Ni2 111.34(17) . 17_554
N8 N7 N6 179.3(5) . .
N10 N9 Ni2 129.7(4) . .
N9 N10 N9 179.7(8) 18_654 .
N1 C1 C2 122.4(5) . .
N1 C1 H1 118.8 . .
C2 C1 H1 118.8 . .
C1 C2 C3 119.7(5) . .
C1 C2 H2 120.1 . .
C3 C2 H2 120.1 . .
C2 C3 C4 118.4(5) . .
C2 C3 H3 120.8 . .
C4 C3 H3 120.8 . .
C5 C4 C3 118.3(5) . .
C5 C4 H4 120.9 . .
C3 C4 H4 120.9 . .
N1 C5 C4 121.4(5) . .
N1 C5 C6 116.1(4) . .
C4 C5 C6 122.5(5) . .
N2 C6 C5 115.6(4) . .
N2 C6 C7 123.9(4) . .
C5 C6 C7 120.5(4) . .
C8 C7 C12 119.9(5) . .
C8 C7 C6 119.9(5) . .
C12 C7 C6 120.2(5) . .
C7 C8 C9 118.3(7) . .
C7 C8 H8 120.8 . .
C9 C8 H8 120.8 . .
C10 C9 C8 120.0(8) . .
C10 C9 H9 120.0 . .
C8 C9 H9 120.0 . .
C9 C10 C11 121.8(8) . .
C9 C10 H10 119.1 . .
C11 C10 H10 119.1 . .
C12 C11 C10 120.1(7) . .
C12 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
C11 C12 C7 119.6(6) . .
C11 C12 H12 120.2 . .
C7 C12 H12 120.2 . .
N3 C13 C14 111.0(5) . .
N3 C13 H13A 109.4 . .
C14 C13 H13A 109.4 . .
N3 C13 H13B 109.4 . .
C14 C13 H13B 109.4 . .
H13A C13 H13B 108.0 . .
C13 C14 C15 112.8(5) . .
C13 C14 H14A 109.0 . .
C15 C14 H14A 109.0 . .
C13 C14 H14B 109.0 . .
C15 C14 H14B 109.0 . .
H14A C14 H14B 107.8 . .
N4 C15 C14 116.1(6) . .
N4 C15 H15A 108.3 . .
C14 C15 H15A 108.3 . .
N4 C15 H15B 108.3 . .
C14 C15 H15B 108.3 . .
H15A C15 H15B 107.4 . .
N4 C16 C17 114.0(7) . .
N4 C16 H16A 108.7 . .
C17 C16 H16A 108.7 . .
N4 C16 H16B 108.7 . .
C17 C16 H16B 108.7 . .
H16A C16 H16B 107.6 . .
C17 C18 N5 115.7(7) . .
C17 C18 H18A 108.3 . .
N5 C18 H18A 108.3 . .
C17 C18 H18B 108.3 . .
N5 C18 H18B 108.3 . .
H18A C18 H18B 107.4 . .
C18 C17 C16 113.9(8) . .
C18 C17 H17A 108.8 . .
C16 C17 H17A 108.8 . .
C18 C17 H17B 108.8 . .
C16 C17 H17B 108.8 . .
H17A C17 H17B 107.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N2 2.066(4) 17_554
Ni1 N2 2.066(4) .
Ni1 N1 2.069(4) 17_554
Ni1 N1 2.069(4) .
Ni1 N6 2.126(4) .
Ni1 N6 2.126(4) 17_554
Ni2 O1 2.040(3) .
Ni2 N3 2.059(4) .
Ni2 N9 2.100(5) .
Ni2 N5 2.100(5) .
Ni2 N4 2.103(5) .
Ni2 N6 2.159(4) 17_554
O1 N2 1.322(5) .
N1 C1 1.334(6) .
N1 C5 1.354(6) .
N2 C6 1.291(6) .
N3 C13 1.462(7) .
N3 H3A 0.9000 .
N3 H3B 0.9000 .
N4 C15 1.414(8) .
N4 C16 1.501(9) .
N4 H4O 0.9100 .
N5 C18 1.474(9) .
N5 H5A 0.9000 .
N5 H5B 0.9000 .
N6 N7 1.215(6) .
N6 Ni2 2.159(4) 17_554
N7 N8 1.164(6) .
N9 N10 1.156(6) .
N10 N9 1.156(6) 18_654
C1 C2 1.366(7) .
C1 H1 0.9300 .
C2 C3 1.383(8) .
C2 H2 0.9300 .
C3 C4 1.426(8) .
C3 H3 0.9300 .
C4 C5 1.386(7) .
C4 H4 0.9300 .
C5 C6 1.470(7) .
C6 C7 1.480(7) .
C7 C8 1.359(8) .
C7 C12 1.426(8) .
C8 C9 1.476(10) .
C8 H8 0.9300 .
C9 C10 1.308(11) .
C9 H9 0.9300 .
C10 C11 1.392(11) .
C10 H10 0.9300 .
C11 C12 1.374(9) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 C14 1.521(8) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.521(10) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.507(11) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C18 C17 1.458(8) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
O1W O1W 0.73(10) 19
