#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:16:12 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179474 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/71/4337191.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_4337191
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(N O3), C2 H3 N, N3'
_chemical_formula_sum            'C110 H159 N63 Ni9 O12'
_chemical_formula_weight         3084.39
_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                   17.8824(3)
_cell_length_b                   17.8824(3)
_cell_length_c                   72.9661(14)
_cell_measurement_reflns_used    9846
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.4
_cell_measurement_theta_min      2.28
_cell_volume                     20207.1(6)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker X8 KappaAPEXII'
_diffrn_measurement_method       'omega and phi 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  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0147
_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       91
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            69558
_diffrn_reflns_theta_full        26.45
_diffrn_reflns_theta_max         26.45
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    1.310
_exptl_absorpt_correction_T_max  0.81
_exptl_absorpt_correction_T_min  0.51
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             9648
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4621
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0412P)²+28.1880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                3954
_reflns_number_total             4621
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic402651k_si_001.cif
_cod_data_source_block           af09tf1na
_cod_original_sg_symbol_H-M      R-3c
_cod_database_code               4337191
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 0.326232(18) 0.3333 0.0833 0.02210(9) Uani 1 2 d SU
Ni2 Ni 0.515097(16) 0.473769(16) 0.058577(3) 0.02900(9) Uani 1 1 d U
O1 O 0.39613(9) 0.42003(9) 0.046804(18) 0.0311(3) Uani 1 1 d .
N1 N 0.20175(10) 0.24427(10) 0.07584(2) 0.0242(3) Uani 1 1 d .
N2 N 0.32868(10) 0.35803(10) 0.05590(2) 0.0255(3) Uani 1 1 d U
N3 N 0.51566(11) 0.35902(11) 0.05638(2) 0.0321(4) Uani 1 1 d .
H3A H 0.5688 0.3694 0.0594 0.039 Uiso 1 1 calc R
H3B H 0.4789 0.3224 0.0648 0.039 Uiso 1 1 calc R
N4 N 0.56972(14) 0.51553(14) 0.03236(3) 0.0433(4) Uani 1 1 d U
H4N H 0.631(2) 0.540(2) 0.0342(4) 0.076(10) Uiso 1 1 d .
N5 N 0.51334(14) 0.58961(13) 0.06233(3) 0.0489(5) Uani 1 1 d U
H5A H 0.4660 0.5837 0.0566 0.059 Uiso 1 1 calc R
H5B H 0.5064 0.5949 0.0744 0.059 Uiso 1 1 calc R
N6 N 0.36037(10) 0.23592(10) 0.08116(2) 0.0275(3) Uani 1 1 d .
N7 N 0.32560(10) 0.18389(11) 0.06899(2) 0.0268(3) Uani 1 1 d .
N8 N 0.29152(12) 0.13414(12) 0.05748(3) 0.0377(4) Uani 1 1 d .
N9 N 0.64313(13) 0.53117(15) 0.06836(3) 0.0544(6) Uani 1 1 d U
N10 N 0.6667 0.54269(13) 0.0833 0.0310(5) Uani 1 2 d SU
C1 C 0.13926(12) 0.18675(12) 0.08676(3) 0.0287(4) Uani 1 1 d .
H1 H 0.1518 0.1841 0.0990 0.034 Uiso 1 1 calc R
C2 C 0.05634(13) 0.13096(14) 0.08043(3) 0.0340(4) Uani 1 1 d .
H2 H 0.0143 0.0912 0.0883 0.041 Uiso 1 1 calc R
C3 C 0.03761(14) 0.13561(14) 0.06240(3) 0.0363(5) Uani 1 1 d .
H3 H -0.0179 0.1001 0.0579 0.044 Uiso 1 1 calc R
C4 C 0.10240(13) 0.19395(14) 0.05092(3) 0.0325(4) Uani 1 1 d .
H4 H 0.0909 0.1975 0.0386 0.039 Uiso 1 1 calc R
C5 C 0.18491(12) 0.24715(12) 0.05795(3) 0.0256(4) Uani 1 1 d .
C6 C 0.25767(12) 0.31043(12) 0.04682(2) 0.0256(4) Uani 1 1 d .
C7 C 0.24793(13) 0.31912(15) 0.02683(3) 0.0337(4) Uani 1 1 d .
C8 C 0.22615(17) 0.24895(19) 0.01549(3) 0.0544(6) Uani 1 1 d U
H8 H 0.2213 0.1984 0.0202 0.065 Uiso 1 1 calc R
C9 C 0.2113(2) 0.2555(2) -0.00339(4) 0.0752(9) Uani 1 1 d U
H9 H 0.1968 0.2094 -0.0113 0.090 Uiso 1 1 calc R
C10 C 0.2189(2) 0.3321(3) -0.00988(4) 0.0780(9) Uani 1 1 d U
H10 H 0.2051 0.3352 -0.0220 0.094 Uiso 1 1 calc R
C11 C 0.2458(2) 0.4024(2) 0.00104(4) 0.0682(8) Uani 1 1 d U
H11 H 0.2549 0.4544 -0.0038 0.082 Uiso 1 1 calc R
C12 C 0.25937(17) 0.39581(18) 0.01931(3) 0.0504(6) Uani 1 1 d U
H12 H 0.2766 0.4436 0.0269 0.060 Uiso 1 1 calc R
C13 C 0.49254(15) 0.31424(15) 0.03843(3) 0.0400(5) Uani 1 1 d .
H13A H 0.4332 0.2970 0.0354 0.048 Uiso 1 1 calc R
H13B H 0.4974 0.2627 0.0391 0.048 Uiso 1 1 calc R
C14 C 0.55351(18) 0.37509(17) 0.02335(3) 0.0519(6) Uani 1 1 d .
H14A H 0.6127 0.3983 0.0274 0.062 Uiso 1 1 calc R
H14B H 0.5459 0.3413 0.0124 0.062 Uiso 1 1 calc R
C15 C 0.54016(18) 0.44868(18) 0.01846(3) 0.0536(7) Uani 1 1 d .
H15A H 0.5704 0.4742 0.0071 0.064 Uiso 1 1 calc R
H15B H 0.4791 0.4265 0.0163 0.064 Uiso 1 1 calc R
C16 C 0.5718(2) 0.5968(2) 0.02603(4) 0.0674(8) Uani 1 1 d U
H16A H 0.5970 0.6113 0.0139 0.081 Uiso 1 1 calc R
H16B H 0.5130 0.5857 0.0251 0.081 Uiso 1 1 calc R
C17 C 0.6219(2) 0.6730(2) 0.03843(5) 0.0752(9) Uani 1 1 d .
H17A H 0.6788 0.6798 0.0401 0.090 Uiso 1 1 calc R
H17B H 0.6297 0.7239 0.0320 0.090 Uiso 1 1 calc R
C18 C 0.5888(3) 0.6729(2) 0.05598(5) 0.0889(12) Uani 1 1 d U
H18A H 0.5721 0.7168 0.0562 0.107 Uiso 1 1 calc R
H18B H 0.6352 0.6900 0.0648 0.107 Uiso 1 1 calc R
N11 N 0.6667 0.3333 0.06585(5) 0.0502(9) Uani 1 3 d SD
N12 N 0.6667 0.3333 0.0833 0.0337(10) Uani 1 6 d SD
N13 N 0.0000 0.0000 0.12268(10) 0.113(2) Uani 1 3 d S
O12 O 0.0824(2) 0.0528(2) 0.12253(4) 0.1198(11) Uani 1 1 d .
N14 N 0.0000 0.0000 -0.01624(11) 0.120(3) Uani 0.50 3 d SP
C19 C 0.0000 0.0000 0.0000 0.116(5) Uani 1 6 d S
C20 C 0.0000 0.0000 -0.01624(11) 0.120(3) Uani 0.50 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'
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
N2 Ni1 N2 170.07(9) 18_554 .
N2 Ni1 N1 78.79(6) 18_554 18_554
N2 Ni1 N1 94.26(6) . 18_554
N2 Ni1 N1 94.27(6) 18_554 .
N2 Ni1 N1 78.78(6) . .
N1 Ni1 N1 92.12(9) 18_554 .
N2 Ni1 N6 90.04(6) 18_554 .
N2 Ni1 N6 96.91(6) . .
N1 Ni1 N6 168.81(6) 18_554 .
N1 Ni1 N6 89.35(6) . .
N2 Ni1 N6 96.91(6) 18_554 18_554
N2 Ni1 N6 90.04(6) . 18_554
N1 Ni1 N6 89.36(6) 18_554 18_554
N1 Ni1 N6 168.80(6) . 18_554
N6 Ni1 N6 91.35(9) . 18_554
O1 Ni2 N3 91.23(6) . .
O1 Ni2 N5 89.60(7) . .
N3 Ni2 N5 176.94(7) . .
O1 Ni2 N4 88.52(7) . .
N3 Ni2 N4 92.87(7) . .
N5 Ni2 N4 90.09(8) . .
O1 Ni2 N9 174.79(7) . .
N3 Ni2 N9 88.07(8) . .
N5 Ni2 N9 91.36(9) . .
N4 Ni2 N9 86.37(8) . .
O1 Ni2 N6 91.03(6) . 18_554
N3 Ni2 N6 87.36(6) . 18_554
N5 Ni2 N6 89.68(7) . 18_554
N4 Ni2 N6 179.49(7) . 18_554
N9 Ni2 N6 94.09(7) . 18_554
N2 O1 Ni2 118.59(10) . .
C1 N1 C5 119.34(16) . .
C1 N1 Ni1 126.87(13) . .
C5 N1 Ni1 113.80(12) . .
C6 N2 O1 118.02(15) . .
C6 N2 Ni1 116.65(13) . .
O1 N2 Ni1 125.31(11) . .
C13 N3 Ni2 117.85(13) . .
C13 N3 H3A 107.8 . .
Ni2 N3 H3A 107.8 . .
C13 N3 H3B 107.8 . .
Ni2 N3 H3B 107.8 . .
H3A N3 H3B 107.2 . .
C15 N4 C16 113.8(2) . .
C15 N4 Ni2 115.42(16) . .
C16 N4 Ni2 113.77(16) . .
C15 N4 H4N 109.8(19) . .
C16 N4 H4N 96.9(19) . .
Ni2 N4 H4N 105.0(19) . .
C18 N5 Ni2 119.3(2) . .
C18 N5 H5A 107.5 . .
Ni2 N5 H5A 107.5 . .
C18 N5 H5B 107.5 . .
Ni2 N5 H5B 107.5 . .
H5A N5 H5B 107.0 . .
N7 N6 Ni1 116.02(12) . .
N7 N6 Ni2 119.87(13) . 18_554
Ni1 N6 Ni2 110.89(7) . 18_554
N8 N7 N6 179.2(2) . .
N10 N9 Ni2 128.19(15) . .
N9 N10 N9 179.6(3) 17_654 .
N1 C1 C2 122.36(18) . .
N1 C1 H1 118.8 . .
C2 C1 H1 118.8 . .
C3 C2 C1 118.8(2) . .
C3 C2 H2 120.6 . .
C1 C2 H2 120.6 . .
C2 C3 C4 119.2(2) . .
C2 C3 H3 120.4 . .
C4 C3 H3 120.4 . .
C3 C4 C5 119.52(19) . .
C3 C4 H4 120.2 . .
C5 C4 H4 120.2 . .
N1 C5 C4 120.75(17) . .
N1 C5 C6 115.88(16) . .
C4 C5 C6 123.35(17) . .
N2 C6 C5 114.85(16) . .
N2 C6 C7 123.93(17) . .
C5 C6 C7 121.19(17) . .
C8 C7 C12 119.5(2) . .
C8 C7 C6 119.1(2) . .
C12 C7 C6 121.5(2) . .
C7 C8 C9 119.0(3) . .
C7 C8 H8 120.5 . .
C9 C8 H8 120.5 . .
C10 C9 C8 118.8(3) . .
C10 C9 H9 120.6 . .
C8 C9 H9 120.6 . .
C11 C10 C9 121.8(3) . .
C11 C10 H10 119.1 . .
C9 C10 H10 119.1 . .
C10 C11 C12 119.2(3) . .
C10 C11 H11 120.4 . .
C12 C11 H11 120.4 . .
C11 C12 C7 121.5(3) . .
C11 C12 H12 119.3 . .
C7 C12 H12 119.3 . .
N3 C13 C14 109.89(19) . .
N3 C13 H13A 109.7 . .
C14 C13 H13A 109.7 . .
N3 C13 H13B 109.7 . .
C14 C13 H13B 109.7 . .
H13A C13 H13B 108.2 . .
C15 C14 C13 115.0(2) . .
C15 C14 H14A 108.5 . .
C13 C14 H14A 108.5 . .
C15 C14 H14B 108.5 . .
C13 C14 H14B 108.5 . .
H14A C14 H14B 107.5 . .
N4 C15 C14 114.0(2) . .
N4 C15 H15A 108.8 . .
C14 C15 H15A 108.8 . .
N4 C15 H15B 108.8 . .
C14 C15 H15B 108.8 . .
H15A C15 H15B 107.7 . .
C17 C16 N4 113.9(3) . .
C17 C16 H16A 108.8 . .
N4 C16 H16A 108.8 . .
C17 C16 H16B 108.8 . .
N4 C16 H16B 108.8 . .
H16A C16 H16B 107.7 . .
C18 C17 C16 119.1(3) . .
C18 C17 H17A 107.5 . .
C16 C17 H17A 107.5 . .
C18 C17 H17B 107.5 . .
C16 C17 H17B 107.5 . .
H17A C17 H17B 107.0 . .
C17 C18 N5 116.7(3) . .
C17 C18 H18A 108.1 . .
N5 C18 H18A 108.1 . .
C17 C18 H18B 108.1 . .
N5 C18 H18B 108.1 . .
H18A C18 H18B 107.3 . .
N11 N12 N11 180.0 16_544 .
O12 N13 O12 119.994(18) . 3
O12 N13 O12 119.994(18) . 2
O12 N13 O12 119.994(18) 3 2
C20 C19 N14 180.0 19 .
N14 C19 N14 180.0 19 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N2 2.0451(15) 18_554
Ni1 N2 2.0453(15) .
Ni1 N1 2.0604(15) 18_554
Ni1 N1 2.0605(15) .
Ni1 N6 2.1204(16) .
Ni1 N6 2.1204(16) 18_554
Ni2 O1 2.0355(14) .
Ni2 N3 2.0632(17) .
Ni2 N5 2.105(2) .
Ni2 N4 2.1075(19) .
Ni2 N9 2.111(2) .
Ni2 N6 2.1714(16) 18_554
O1 N2 1.337(2) .
N1 C1 1.339(2) .
N1 C5 1.346(2) .
N2 C6 1.302(2) .
N3 C13 1.482(3) .
N3 H3A 0.9000 .
N3 H3B 0.9000 .
N4 C15 1.451(3) .
N4 C16 1.508(4) .
N4 H4N 0.96(3) .
N5 C18 1.499(4) .
N5 H5A 0.9000 .
N5 H5B 0.9000 .
N6 N7 1.209(2) .
N6 Ni2 2.1715(16) 18_554
N7 N8 1.152(2) .
N9 N10 1.152(2) .
N10 N9 1.152(2) 17_654
C1 C2 1.389(3) .
C1 H1 0.9300 .
C2 C3 1.371(3) .
C2 H2 0.9300 .
C3 C4 1.387(3) .
C3 H3 0.9300 .
C4 C5 1.393(3) .
C4 H4 0.9300 .
C5 C6 1.470(3) .
C6 C7 1.486(3) .
C7 C8 1.386(3) .
C7 C12 1.394(3) .
C8 C9 1.419(4) .
C8 H8 0.9300 .
C9 C10 1.390(5) .
C9 H9 0.9300 .
C10 C11 1.357(5) .
C10 H10 0.9300 .
C11 C12 1.370(4) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 C14 1.548(3) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.493(4) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.502(5) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18 1.411(4) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
N11 N12 1.275(4) .
N12 N11 1.275(4) 16_544
N13 O12 1.293(3) .
N13 O12 1.293(3) 3
N13 O12 1.293(3) 2
N14 C19 1.185(8) .
C19 C20 1.185(8) 19
C19 N14 1.185(8) 19
