#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:16:12 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179474 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/71/4337194.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_4337194
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         '2(C108 H156 N57 Ni9 O6), Cl4, 2(N3), (H2 O)'
_chemical_formula_sum            'C216 H314 Cl4 N120 Ni18 O13'
_chemical_formula_weight         5998.45
_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            3
_cell_length_a                   18.0085(9)
_cell_length_b                   18.0085(9)
_cell_length_c                   73.205(5)
_cell_measurement_reflns_used    1962
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.25
_cell_measurement_theta_min      2.26
_cell_volume                     20560(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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       90
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4756
_diffrn_reflns_theta_full        26.60
_diffrn_reflns_theta_max         26.60
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    1.319
_exptl_absorpt_correction_T_max  0.9100
_exptl_absorpt_correction_T_min  0.6814
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             9378
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4756
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0379
_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)+(0.0693P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                3058
_reflns_number_total             4756
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic402651k_si_001.cif
_cod_data_source_block           af03fua2na
_cod_original_sg_symbol_H-M      R-3c
_cod_database_code               4337194
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'-x, -x+y, -z+1/2'
'x-y, -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+2/3, -x+y+1/3, -z+5/6'
'x-y+2/3, -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+1/3, -x+y+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'x, x-y, z-1/2'
'-x+y, 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+2/3, x-y+1/3, z-1/6'
'-x+y+2/3, 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+1/3, x-y+2/3, z+1/6'
'-x+y+1/3, 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 0.32648(3) 0.3333 0.0833 0.04244(17) Uani 1 2 d S
Ni2 Ni 0.51428(3) 0.47105(3) 0.058743(6) 0.05092(16) Uani 1 1 d .
Cl1 Cl 0.3641(10) 0.5999(9) 0.04264(13) 0.137(4) Uani 0.17 1 d P
Cl1' Cl 0.4113(6) 0.6609(12) 0.04046(17) 0.193(9) Uani 0.17 1 d P
O1 O 0.39559(14) 0.41554(15) 0.04680(3) 0.0557(6) Uani 1 1 d .
N1 N 0.20286(16) 0.24443(17) 0.07610(4) 0.0476(6) Uani 1 1 d .
N2 N 0.32884(16) 0.35666(18) 0.05594(4) 0.0471(6) Uani 1 1 d .
N3 N 0.5133(2) 0.58655(19) 0.06214(5) 0.0828(10) Uani 1 1 d .
H3A H 0.4670 0.5812 0.0562 0.099 Uiso 1 1 calc R
H3B H 0.5057 0.5922 0.0741 0.099 Uiso 1 1 calc R
N4 N 0.5679(2) 0.5110(2) 0.03245(4) 0.0724(8) Uani 1 1 d U
H4 H 0.6239 0.5263 0.0340 0.087 Uiso 1 1 calc R
N5 N 0.51546(15) 0.35754(17) 0.05686(3) 0.0494(6) Uani 1 1 d .
H5A H 0.5682 0.3682 0.0600 0.059 Uiso 1 1 calc R
H5B H 0.4787 0.3213 0.0653 0.059 Uiso 1 1 calc R
N6 N 0.36055(16) 0.23695(16) 0.08122(3) 0.0450(6) Uani 1 1 d .
N7 N 0.32586(16) 0.18452(17) 0.06924(4) 0.0445(6) Uani 1 1 d .
N8 N 0.29154(17) 0.13511(19) 0.05779(4) 0.0567(7) Uani 1 1 d .
N9 N 0.6411(2) 0.5289(2) 0.06851(5) 0.0842(11) Uani 1 1 d U
N10 N 0.6667 0.5419(2) 0.0833 0.0545(10) Uani 1 2 d SU
N11 N 0.6667 0.3333 0.0833 0.0368(13) Uani 1 6 d S
N12 N 0.6667 0.3333 0.06707(9) 0.0679(15) Uani 1 3 d S
C1 C 0.1412(2) 0.1880(2) 0.08709(5) 0.0554(8) Uani 1 1 d .
H1 H 0.1545 0.1855 0.0993 0.066 Uiso 1 1 calc R
C2 C 0.0586(2) 0.1331(2) 0.08112(5) 0.0630(10) Uani 1 1 d .
H2 H 0.0170 0.0943 0.0891 0.076 Uiso 1 1 calc R
C3 C 0.0395(2) 0.1375(3) 0.06280(6) 0.0678(10) Uani 1 1 d .
H3 H -0.0156 0.1021 0.0583 0.081 Uiso 1 1 calc R
C4 C 0.1032(2) 0.1947(2) 0.05146(5) 0.0610(9) Uani 1 1 d .
H4A H 0.0913 0.1979 0.0392 0.073 Uiso 1 1 calc R
C5 C 0.1852(2) 0.2477(2) 0.05815(5) 0.0494(8) Uani 1 1 d .
C6 C 0.2578(2) 0.3096(2) 0.04700(4) 0.0493(8) Uani 1 1 d .
C7 C 0.2470(2) 0.3165(3) 0.02707(5) 0.0683(10) Uani 1 1 d U
C8 C 0.2542(4) 0.3906(4) 0.01993(6) 0.127(2) Uani 1 1 d U
H8 H 0.2688 0.4378 0.0274 0.152 Uiso 1 1 calc R
C9 C 0.2391(5) 0.3934(6) 0.00143(9) 0.181(4) Uani 1 1 d U
H9 H 0.2430 0.4428 -0.0035 0.218 Uiso 1 1 calc R
C10 C 0.2188(5) 0.3250(9) -0.00981(9) 0.193(4) Uani 1 1 d U
H10 H 0.2081 0.3273 -0.0222 0.231 Uiso 1 1 calc R
C11 C 0.2147(4) 0.2568(6) -0.00275(8) 0.172(4) Uani 1 1 d U
H11 H 0.2012 0.2101 -0.0103 0.206 Uiso 1 1 calc R
C12 C 0.2302(3) 0.2514(4) 0.01586(6) 0.1040(16) Uani 1 1 d .
H12 H 0.2287 0.2025 0.0204 0.125 Uiso 1 1 calc R
C13 C 0.5888(4) 0.6674(3) 0.05594(8) 0.148(3) Uani 1 1 d .
H13A H 0.5751 0.7130 0.0568 0.177 Uiso 1 1 calc R
H13B H 0.6358 0.6814 0.0643 0.177 Uiso 1 1 calc R
C14 C 0.6168(5) 0.6666(3) 0.03816(9) 0.137(3) Uani 1 1 d .
H14A H 0.6754 0.6781 0.0391 0.165 Uiso 1 1 calc R
H14B H 0.6193 0.7151 0.0318 0.165 Uiso 1 1 calc R
C15 C 0.5721(4) 0.5930(4) 0.02614(7) 0.1154(18) Uani 1 1 d U
H15A H 0.5999 0.6081 0.0143 0.138 Uiso 1 1 calc R
H15B H 0.5140 0.5819 0.0245 0.138 Uiso 1 1 calc R
C16 C 0.5383(3) 0.4447(3) 0.01877(5) 0.0873(12) Uani 1 1 d U
H16A H 0.5686 0.4694 0.0074 0.105 Uiso 1 1 calc R
H16B H 0.4778 0.4231 0.0166 0.105 Uiso 1 1 calc R
C17 C 0.5513(3) 0.3698(3) 0.02418(5) 0.0820(11) Uani 1 1 d U
H17A H 0.5422 0.3346 0.0134 0.098 Uiso 1 1 calc R
H17B H 0.6104 0.3928 0.0279 0.098 Uiso 1 1 calc R
C18 C 0.4939(2) 0.3128(2) 0.03928(5) 0.0651(10) Uani 1 1 d .
H18A H 0.4347 0.2942 0.0363 0.078 Uiso 1 1 calc R
H18B H 0.4998 0.2622 0.0402 0.078 Uiso 1 1 calc R
O1W O 0.0000 0.0000 0.0096(8) 0.32(4) Uani 0.25 3 d SP
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'
Ni Ni 0.3393 1.1124 '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'
O O 0.0106 0.0060 '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 170.60(14) 18_554 .
N2 Ni1 N1 79.11(11) 18_554 18_554
N2 Ni1 N1 94.33(10) . 18_554
N2 Ni1 N1 94.33(10) 18_554 .
N2 Ni1 N1 79.10(11) . .
N1 Ni1 N1 92.30(14) 18_554 .
N2 Ni1 N6 90.14(10) 18_554 .
N2 Ni1 N6 96.44(10) . .
N1 Ni1 N6 169.22(10) 18_554 .
N1 Ni1 N6 89.29(10) . .
N2 Ni1 N6 96.45(10) 18_554 18_554
N2 Ni1 N6 90.14(10) . 18_554
N1 Ni1 N6 89.29(10) 18_554 18_554
N1 Ni1 N6 169.21(10) . 18_554
N6 Ni1 N6 91.14(14) . 18_554
O1 Ni2 N5 90.75(9) . .
O1 Ni2 N3 90.59(13) . .
N5 Ni2 N3 177.06(12) . .
O1 Ni2 N9 174.54(11) . .
N5 Ni2 N9 88.13(12) . .
N3 Ni2 N9 90.78(15) . .
O1 Ni2 N4 88.00(11) . .
N5 Ni2 N4 92.69(12) . .
N3 Ni2 N4 89.98(13) . .
N9 Ni2 N4 86.72(13) . .
O1 Ni2 N6 90.89(9) . 18_554
N5 Ni2 N6 87.65(10) . 18_554
N3 Ni2 N6 89.71(11) . 18_554
N9 Ni2 N6 94.40(11) . 18_554
N4 Ni2 N6 178.84(11) . 18_554
Cl1' Cl1 Cl1' 111.4(11) . 3_565
Cl1 Cl1' Cl1 125.9(14) . 2_665
N2 O1 Ni2 118.98(17) . .
C1 N1 C5 119.4(3) . .
C1 N1 Ni1 127.0(2) . .
C5 N1 Ni1 113.6(2) . .
C6 N2 O1 118.1(3) . .
C6 N2 Ni1 116.5(2) . .
O1 N2 Ni1 125.40(19) . .
C13 N3 Ni2 118.6(3) . .
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 . .
C16 N4 C15 114.4(4) . .
C16 N4 Ni2 115.8(3) . .
C15 N4 Ni2 113.7(3) . .
C16 N4 H4 103.6 . .
C15 N4 H4 103.6 . .
Ni2 N4 H4 103.6 . .
C18 N5 Ni2 118.3(2) . .
C18 N5 H5A 107.7 . .
Ni2 N5 H5A 107.7 . .
C18 N5 H5B 107.7 . .
Ni2 N5 H5B 107.7 . .
H5A N5 H5B 107.1 . .
N7 N6 Ni1 116.44(19) . .
N7 N6 Ni2 119.5(2) . 18_554
Ni1 N6 Ni2 111.09(11) . 18_554
N8 N7 N6 178.5(3) . .
N10 N9 Ni2 130.0(2) . .
N9 N10 N9 179.6(6) 17_654 .
N12 N11 N12 180.0 16_544 .
N1 C1 C2 122.8(3) . .
N1 C1 H1 118.6 . .
C2 C1 H1 118.6 . .
C1 C2 C3 118.1(3) . .
C1 C2 H2 121.0 . .
C3 C2 H2 121.0 . .
C4 C3 C2 119.1(3) . .
C4 C3 H3 120.5 . .
C2 C3 H3 120.5 . .
C3 C4 C5 120.4(3) . .
C3 C4 H4A 119.8 . .
C5 C4 H4A 119.8 . .
N1 C5 C4 120.2(3) . .
N1 C5 C6 115.5(3) . .
C4 C5 C6 124.3(3) . .
N2 C6 C5 115.2(3) . .
N2 C6 C7 124.5(3) . .
C5 C6 C7 120.3(3) . .
C12 C7 C8 119.1(4) . .
C12 C7 C6 120.8(4) . .
C8 C7 C6 120.1(4) . .
C7 C8 C9 118.7(6) . .
C7 C8 H8 120.6 . .
C9 C8 H8 120.6 . .
C10 C9 C8 121.5(7) . .
C10 C9 H9 119.2 . .
C8 C9 H9 119.2 . .
C11 C10 C9 118.3(6) . .
C11 C10 H10 120.9 . .
C9 C10 H10 120.9 . .
C10 C11 C12 122.1(8) . .
C10 C11 H11 119.0 . .
C12 C11 H11 119.0 . .
C7 C12 C11 120.2(6) . .
C7 C12 H12 119.9 . .
C11 C12 H12 119.9 . .
C14 C13 N3 115.6(5) . .
C14 C13 H13A 108.4 . .
N3 C13 H13A 108.4 . .
C14 C13 H13B 108.4 . .
N3 C13 H13B 108.4 . .
H13A C13 H13B 107.4 . .
C13 C14 C15 122.4(5) . .
C13 C14 H14A 106.7 . .
C15 C14 H14A 106.7 . .
C13 C14 H14B 106.7 . .
C15 C14 H14B 106.7 . .
H14A C14 H14B 106.6 . .
C14 C15 N4 116.1(5) . .
C14 C15 H15A 108.3 . .
N4 C15 H15A 108.3 . .
C14 C15 H15B 108.3 . .
N4 C15 H15B 108.3 . .
H15A C15 H15B 107.4 . .
N4 C16 C17 113.2(4) . .
N4 C16 H16A 108.9 . .
C17 C16 H16A 108.9 . .
N4 C16 H16B 108.9 . .
C17 C16 H16B 108.9 . .
H16A C16 H16B 107.8 . .
C18 C17 C16 115.7(3) . .
C18 C17 H17A 108.4 . .
C16 C17 H17A 108.4 . .
C18 C17 H17B 108.4 . .
C16 C17 H17B 108.4 . .
H17A C17 H17B 107.4 . .
N5 C18 C17 111.5(3) . .
N5 C18 H18A 109.3 . .
C17 C18 H18A 109.3 . .
N5 C18 H18B 109.3 . .
C17 C18 H18B 109.3 . .
H18A C18 H18B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N2 2.044(3) 18_554
Ni1 N2 2.045(3) .
Ni1 N1 2.058(3) 18_554
Ni1 N1 2.058(3) .
Ni1 N6 2.116(2) .
Ni1 N6 2.116(2) 18_554
Ni2 O1 2.048(2) .
Ni2 N5 2.060(3) .
Ni2 N3 2.104(3) .
Ni2 N9 2.105(3) .
Ni2 N4 2.112(3) .
Ni2 N6 2.161(2) 18_554
Cl1 Cl1' 1.011(15) .
Cl1 Cl1' 1.975(19) 3_565
Cl1' Cl1 1.975(19) 2_665
O1 N2 1.320(3) .
N1 C1 1.335(4) .
N1 C5 1.360(4) .
N2 C6 1.304(4) .
N3 C13 1.482(6) .
N3 H3A 0.9000 .
N3 H3B 0.9000 .
N4 C16 1.440(5) .
N4 C15 1.514(6) .
N4 H4 0.9100 .
N5 C18 1.464(4) .
N5 H5A 0.9000 .
N5 H5B 0.9000 .
N6 N7 1.209(3) .
N6 Ni2 2.162(2) 18_554
N7 N8 1.152(4) .
N9 N10 1.156(3) .
N10 N9 1.156(3) 17_654
N11 N12 1.190(6) 16_544
N11 N12 1.190(6) .
C1 C2 1.383(5) .
C1 H1 0.9300 .
C2 C3 1.397(5) .
C2 H2 0.9300 .
C3 C4 1.373(5) .
C3 H3 0.9300 .
C4 C5 1.387(5) .
C4 H4A 0.9300 .
C5 C6 1.470(5) .
C6 C7 1.485(5) .
C7 C12 1.336(6) .
C7 C8 1.377(7) .
C8 C9 1.387(7) .
C8 H8 0.9300 .
C9 C10 1.370(13) .
C9 H9 0.9300 .
C10 C11 1.301(13) .
C10 H10 0.9300 .
C11 C12 1.403(7) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 C14 1.399(7) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.452(7) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.533(6) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18 1.510(5) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
O1W O1W 1.41(12) 19
