#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:16:12 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179474 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/71/4337197.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_4337197
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
'C102 H150 N63 Ni9 O6, 2(Cl O4), 2(C H4 O), N3'
_chemical_formula_sum            'C104 H154 Cl2 N66 Ni9 O16'
_chemical_formula_weight         3184.22
_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                   17.7920(5)
_cell_length_b                   17.7920(5)
_cell_length_c                   72.826(3)
_cell_measurement_reflns_used    9699
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.18
_cell_measurement_theta_min      2.29
_cell_volume                     19964.9(11)
_computing_cell_refinement       'BRUKER APEX2'
_computing_data_collection       'BRUKER APEX2'
_computing_data_reduction        'BRUKER APEX2'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0150
_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       92
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4748
_diffrn_reflns_theta_full        26.80
_diffrn_reflns_theta_max         26.80
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    1.370
_exptl_absorpt_correction_T_max  0.8320
_exptl_absorpt_correction_T_min  0.6564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             9924
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.112
_refine_diff_density_min         -1.065
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4748
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0452
_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)+(0.0542P)²+169.7484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1266
_reflns_number_gt                3874
_reflns_number_total             4748
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic402651k_si_001.cif
_cod_data_source_block           af37fua1n
_cod_original_sg_symbol_H-M      R-3c
_cod_database_code               4337197
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 1.00565(3) 0.3333 0.0833 0.02384(15) Uani 1 2 d S . .
Ni2 Ni 0.95768(3) 0.47353(3) 0.058322(5) 0.02947(13) Uani 1 1 d . . .
O1 O 1.02422(15) 0.41940(16) 0.04667(3) 0.0321(5) Uani 1 1 d . . .
N1 N 1.1350(2) 0.4031(3) 0.01994(5) 0.0548(9) Uani 1 1 d U . .
N2 N 1.02873(17) 0.35690(18) 0.05570(4) 0.0276(6) Uani 1 1 d . . .
N3 N 1.04067(16) 0.24334(17) 0.07615(4) 0.0266(5) Uani 1 1 d . . .
N4 N 0.84255(18) 0.35770(19) 0.05591(4) 0.0314(6) Uani 1 1 d . . .
H4A H 0.8433 0.3206 0.0642 0.038 Uiso 1 1 calc R . .
H4B H 0.7993 0.3674 0.0591 0.038 Uiso 1 1 calc R . .
N5 N 0.9454(2) 0.5161(2) 0.03198(4) 0.0412(7) Uani 1 1 d U . .
H5N H 0.9048 0.5325 0.0335 0.049 Uiso 1 1 calc R . .
N6 N 1.0762(2) 0.5907(2) 0.06169(5) 0.0492(8) Uani 1 1 d U . .
H6A H 1.0885 0.5971 0.0738 0.059 Uiso 1 1 calc R . .
H6B H 1.1177 0.5841 0.0561 0.059 Uiso 1 1 calc R . .
N7 N 0.97131(18) 0.43084(18) 0.08521(4) 0.0292(6) Uani 1 1 d . . .
N8 N 1.00568(18) 0.48418(19) 0.09733(4) 0.0302(6) Uani 1 1 d . . .
N9 N 1.0382(2) 0.5342(2) 0.10885(4) 0.0400(7) Uani 1 1 d . . .
N10 N 0.8857(3) 0.5301(3) 0.06814(4) 0.0525(9) Uani 1 1 d . . .
N11 N 0.8748(2) 0.5415(2) 0.0833 0.0291(8) Uani 1 2 d S . .
N12 N 0.6667 0.3333 0.06710(8) 0.0391(12) Uani 1 3 d S . .
N13 N 0.6667 0.3333 0.0833 0.0310(15) Uani 1 6 d S . .
C1 C 1.1580(3) 0.4071(3) 0.00146(6) 0.0555(12) Uani 1 1 d . . .
H1 H 1.1962 0.4603 -0.0039 0.067 Uiso 1 1 calc R . .
C2 C 1.1241(3) 0.3324(4) -0.00882(6) 0.0643(14) Uani 1 1 d . . .
H2 H 1.1399 0.3341 -0.0210 0.077 Uiso 1 1 calc R . .
C3 C 1.0661(3) 0.2549(4) -0.00061(6) 0.0609(13) Uani 1 1 d . . .
H3 H 1.0414 0.2048 -0.0077 0.073 Uiso 1 1 calc R . .
C4 C 1.0437(2) 0.2484(3) 0.01710(4) 0.0383(8) Uani 1 1 d U . .
H4 H 1.0053 0.1949 0.0223 0.046 Uiso 1 1 calc R . .
C5 C 1.0781(2) 0.3210(3) 0.02712(4) 0.0350(7) Uani 1 1 d U . .
C6 C 1.0545(2) 0.3100(2) 0.04695(4) 0.0293(7) Uani 1 1 d . . .
C7 C 1.0630(2) 0.2460(2) 0.05833(4) 0.0291(7) Uani 1 1 d . . .
C8 C 1.0942(2) 0.1932(2) 0.05184(5) 0.0367(8) Uani 1 1 d . . .
H8 H 1.1111 0.1967 0.0396 0.044 Uiso 1 1 calc R . .
C9 C 1.0998(2) 0.1352(2) 0.06372(5) 0.0403(8) Uani 1 1 d . . .
H9 H 1.1209 0.0999 0.0596 0.048 Uiso 1 1 calc R . .
C10 C 1.0737(2) 0.1305(2) 0.08177(5) 0.0332(7) Uani 1 1 d . . .
H10 H 1.0752 0.0909 0.0899 0.040 Uiso 1 1 calc R . .
C11 C 1.0453(2) 0.1863(2) 0.08747(5) 0.0291(7) Uani 1 1 d . . .
H11 H 1.0287 0.1842 0.0997 0.035 Uiso 1 1 calc R . .
C12 C 0.8201(3) 0.3134(3) 0.03799(5) 0.0405(8) Uani 1 1 d . . .
H12A H 0.7629 0.2621 0.0387 0.049 Uiso 1 1 calc R . .
H12B H 0.8615 0.2951 0.0349 0.049 Uiso 1 1 calc R . .
C13 C 0.8206(3) 0.3736(3) 0.02301(5) 0.0479(10) Uani 1 1 d . . .
H13A H 0.7950 0.3396 0.0120 0.057 Uiso 1 1 calc R . .
H13B H 0.7838 0.3965 0.0269 0.057 Uiso 1 1 calc R . .
C14 C 0.9085(3) 0.4488(3) 0.01817(5) 0.0495(10) Uani 1 1 d . . .
H14A H 0.9481 0.4270 0.0161 0.059 Uiso 1 1 calc R . .
H14B H 0.9038 0.4742 0.0067 0.059 Uiso 1 1 calc R . .
C15 C 1.0239(4) 0.5962(3) 0.02571(7) 0.0689(8) Uani 1 1 d U . .
H15A H 1.0131 0.6101 0.0135 0.083 Uiso 1 1 calc R . .
H15B H 1.0714 0.5843 0.0248 0.083 Uiso 1 1 calc R . .
C16 C 1.0520(4) 0.6736(3) 0.03758(7) 0.0689(8) Uani 1 1 d . . .
H16A H 1.0964 0.7236 0.0310 0.083 Uiso 1 1 calc R . .
H16B H 1.0028 0.6825 0.0391 0.083 Uiso 1 1 calc R . .
C17 C 1.0843(4) 0.6727(3) 0.05502(7) 0.0689(8) Uani 1 1 d U . .
H17A H 1.0554 0.6908 0.0638 0.083 Uiso 1 1 calc R . .
H17B H 1.1454 0.7164 0.0552 0.083 Uiso 1 1 calc R . .
Cl1 Cl 0.0000 0.0000 0.131935(19) 0.0353(3) Uani 1 3 d S . .
O2 O 0.0000 0.0000 0.15115(7) 0.096(3) Uani 1 3 d S . .
O3 O 0.0853(2) 0.0281(2) 0.12505(5) 0.0700(10) Uani 1 1 d . . .
C18 C 0.0000 0.0000 0.0232(2) 0.122(5) Uani 1 3 d SDU . .
O4 O -0.0425(6) 0.0526(6) 0.02311(16) 0.087(3) Uani 0.33 1 d PDU A 1
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'
Cl Cl 0.1484 0.1585 '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'
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 168.77(15) 18_554 .
N2 Ni1 N3 78.59(10) 18_554 18_554
N2 Ni1 N3 93.57(10) . 18_554
N2 Ni1 N3 93.57(10) 18_554 .
N2 Ni1 N3 78.58(10) . .
N3 Ni1 N3 92.30(14) 18_554 .
N2 Ni1 N7 90.36(10) 18_554 18_554
N2 Ni1 N7 97.51(10) . 18_554
N3 Ni1 N7 168.91(10) 18_554 18_554
N3 Ni1 N7 89.33(10) . 18_554
N2 Ni1 N7 97.51(10) 18_554 .
N2 Ni1 N7 90.36(10) . .
N3 Ni1 N7 89.34(10) 18_554 .
N3 Ni1 N7 168.90(10) . .
N7 Ni1 N7 91.17(15) 18_554 .
O1 Ni2 N4 90.78(10) . .
O1 Ni2 N6 89.18(13) . .
N4 Ni2 N6 178.03(12) . .
O1 Ni2 N10 175.29(11) . .
N4 Ni2 N10 88.23(14) . .
N6 Ni2 N10 91.97(16) . .
O1 Ni2 N5 88.87(11) . .
N4 Ni2 N5 92.95(12) . .
N6 Ni2 N5 89.02(13) . .
N10 Ni2 N5 86.58(13) . .
O1 Ni2 N7 90.99(9) . .
N4 Ni2 N7 87.47(11) . .
N6 Ni2 N7 90.55(12) . .
N10 Ni2 N7 93.57(11) . .
N5 Ni2 N7 179.55(14) . .
N2 O1 Ni2 118.68(18) . .
C5 N1 C1 117.0(4) . .
C6 N2 O1 118.8(3) . .
C6 N2 Ni1 116.6(2) . .
O1 N2 Ni1 124.5(2) . .
C11 N3 C7 119.2(3) . .
C11 N3 Ni1 126.2(2) . .
C7 N3 Ni1 114.6(2) . .
C12 N4 Ni2 118.6(2) . .
C12 N4 H4A 107.7 . .
Ni2 N4 H4A 107.7 . .
C12 N4 H4B 107.7 . .
Ni2 N4 H4B 107.7 . .
H4A N4 H4B 107.1 . .
C14 N5 C15 113.6(3) . .
C14 N5 Ni2 114.9(2) . .
C15 N5 Ni2 114.0(3) . .
C14 N5 H5N 104.2 . .
C15 N5 H5N 104.2 . .
Ni2 N5 H5N 104.2 . .
C17 N6 Ni2 119.6(3) . .
C17 N6 H6A 107.4 . .
Ni2 N6 H6A 107.4 . .
C17 N6 H6B 107.4 . .
Ni2 N6 H6B 107.4 . .
H6A N6 H6B 106.9 . .
N8 N7 Ni1 116.7(2) . .
N8 N7 Ni2 119.1(2) . .
Ni1 N7 Ni2 111.09(11) . .
N9 N8 N7 179.5(4) . .
N11 N10 Ni2 127.0(2) . .
N10 N11 N10 179.5(8) 16_544 .
N12 N13 N12 180.0 16_544 .
C2 C1 N1 120.0(4) . .
C2 C1 H1 120.0 . .
N1 C1 H1 120.0 . .
C1 C2 C3 118.6(4) . .
C1 C2 H2 120.7 . .
C3 C2 H2 120.7 . .
C4 C3 C2 123.1(5) . .
C4 C3 H3 118.4 . .
C2 C3 H3 118.4 . .
C5 C4 C3 118.0(4) . .
C5 C4 H4 121.0 . .
C3 C4 H4 121.0 . .
C4 C5 N1 123.3(3) . .
C4 C5 C6 116.0(3) . .
N1 C5 C6 120.7(3) . .
N2 C6 C7 115.1(3) . .
N2 C6 C5 123.8(3) . .
C7 C6 C5 121.0(3) . .
N3 C7 C8 120.9(3) . .
N3 C7 C6 115.1(3) . .
C8 C7 C6 124.1(3) . .
C9 C8 C7 119.4(3) . .
C9 C8 H8 120.3 . .
C7 C8 H8 120.3 . .
C10 C9 C8 119.4(3) . .
C10 C9 H9 120.3 . .
C8 C9 H9 120.3 . .
C9 C10 C11 118.2(3) . .
C9 C10 H10 120.9 . .
C11 C10 H10 120.9 . .
N3 C11 C10 122.8(3) . .
N3 C11 H11 118.6 . .
C10 C11 H11 118.6 . .
N4 C12 C13 110.7(3) . .
N4 C12 H12A 109.5 . .
C13 C12 H12A 109.5 . .
N4 C12 H12B 109.5 . .
C13 C12 H12B 109.5 . .
H12A C12 H12B 108.1 . .
C14 C13 C12 115.5(3) . .
C14 C13 H13A 108.4 . .
C12 C13 H13A 108.4 . .
C14 C13 H13B 108.4 . .
C12 C13 H13B 108.4 . .
H13A C13 H13B 107.5 . .
N5 C14 C13 114.3(3) . .
N5 C14 H14A 108.7 . .
C13 C14 H14A 108.7 . .
N5 C14 H14B 108.7 . .
C13 C14 H14B 108.7 . .
H14A C14 H14B 107.6 . .
N5 C15 C16 115.5(5) . .
N5 C15 H15A 108.4 . .
C16 C15 H15A 108.4 . .
N5 C15 H15B 108.4 . .
C16 C15 H15B 108.4 . .
H15A C15 H15B 107.5 . .
C17 C16 C15 117.9(5) . .
C17 C16 H16A 107.8 . .
C15 C16 H16A 107.8 . .
C17 C16 H16B 107.8 . .
C15 C16 H16B 107.8 . .
H16A C16 H16B 107.2 . .
C16 C17 N6 118.2(4) . .
C16 C17 H17A 107.8 . .
N6 C17 H17A 107.8 . .
C16 C17 H17B 107.8 . .
N6 C17 H17B 107.8 . .
H17A C17 H17B 107.1 . .
O2 Cl1 O3 110.53(16) . 3
O2 Cl1 O3 110.53(16) . 2
O3 Cl1 O3 108.39(17) 3 2
O2 Cl1 O3 110.53(16) . .
O3 Cl1 O3 108.39(17) 3 .
O3 Cl1 O3 108.39(17) 2 .
O4 C18 O4 120.00(2) 2 3
O4 C18 O4 120.00(2) 2 .
O4 C18 O4 120.00(2) 3 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N2 2.054(3) 18_554
Ni1 N2 2.055(3) .
Ni1 N3 2.055(3) 18_554
Ni1 N3 2.055(3) .
Ni1 N7 2.112(3) 18_554
Ni1 N7 2.112(3) .
Ni2 O1 2.047(2) .
Ni2 N4 2.062(3) .
Ni2 N6 2.110(3) .
Ni2 N10 2.110(3) .
Ni2 N5 2.114(3) .
Ni2 N7 2.158(3) .
O1 N2 1.328(3) .
N1 C5 1.398(5) .
N1 C1 1.398(5) .
N2 C6 1.303(4) .
N3 C11 1.342(4) .
N3 C7 1.351(4) .
N4 C12 1.473(4) .
N4 H4A 0.9000 .
N4 H4B 0.9000 .
N5 C14 1.445(5) .
N5 C15 1.484(6) .
N5 H5N 0.9100 .
N6 C17 1.475(6) .
N6 H6A 0.9000 .
N6 H6B 0.9000 .
N7 N8 1.213(4) .
N8 N9 1.147(4) .
N10 N11 1.158(3) .
N11 N10 1.158(3) 16_544
N12 N13 1.182(6) .
N13 N12 1.182(6) 16_544
C1 C2 1.375(7) .
C1 H1 0.9300 .
C2 C3 1.378(7) .
C2 H2 0.9300 .
C3 C4 1.338(5) .
C3 H3 0.9300 .
C4 C5 1.336(5) .
C4 H4 0.9300 .
C5 C6 1.489(4) .
C6 C7 1.476(5) .
C7 C8 1.390(5) .
C8 C9 1.387(5) .
C8 H8 0.9300 .
C9 C10 1.383(5) .
C9 H9 0.9300 .
C10 C11 1.384(5) .
C10 H10 0.9300 .
C11 H11 0.9300 .
C12 C13 1.526(5) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.507(6) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C16 1.485(7) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.398(6) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
Cl1 O2 1.399(5) .
Cl1 O3 1.430(3) 3
Cl1 O3 1.430(3) 2
Cl1 O3 1.430(3) .
C18 O4 1.468(6) 2
C18 O4 1.468(6) 3
C18 O4 1.468(6) .
