#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:32:24 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179250 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/70/4317085.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_4317085
loop_
_publ_author_name
'David Martin'
'Matthieu Rouffet'
'Seth M. Cohen'
_publ_section_title
;
 Illuminating Metal-Ion Sensors: Benzimidazolesulfonamide Metal Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              10226
_journal_page_last               10228
_journal_paper_doi               10.1021/ic101700t
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C46 H44 N8 Ni O6 S2'
_chemical_formula_weight         927.72
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 95.1570(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.1240(12)
_cell_length_b                   16.2677(12)
_cell_length_c                   15.5935(11)
_cell_measurement_reflns_used    3971
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.42
_cell_measurement_theta_min      1.73
_cell_volume                     4326.3(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_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  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18376
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.42
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  0.8886
_exptl_absorpt_correction_T_min  0.8635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0448
_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)+(0.0556P)²+12.7395P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1240
_reflns_number_gt                3339
_reflns_number_total             3971
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic101700t_si_001_3.cif
_cod_data_source_block           Ni(TPBI)2
_cod_database_code               4317085
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.0000 0.04443(3) 0.7500 0.01688(16) Uani 1 2 d S . .
S1 S 0.13365(4) 0.14269(4) 0.81503(4) 0.01754(18) Uani 1 1 d . . .
O1 O 0.06571(11) 0.14037(12) 0.86577(12) 0.0203(4) Uani 1 1 d . . .
O2 O 0.20801(12) 0.12391(13) 0.86233(13) 0.0229(5) Uani 1 1 d . . .
O3A O 0.5307(3) 0.1221(4) 0.8302(4) 0.052(2) Uani 0.456(7) 1 d P A 1
O3B O 0.5300(3) 0.0791(4) 0.9694(4) 0.0589(19) Uani 0.544(7) 1 d P A 2
N1 N 0.00450(13) -0.03351(14) 0.65455(15) 0.0181(5) Uani 1 1 d . . .
N2 N 0.03938(14) -0.09363(15) 0.53694(16) 0.0192(5) Uani 1 1 d . . .
H2N H 0.0621(19) -0.102(2) 0.493(2) 0.023 Uiso 1 1 d . . .
N3 N 0.10813(13) 0.08239(14) 0.73645(15) 0.0176(5) Uani 1 1 d . . .
N4 N 0.43531(18) 0.1681(2) 0.9116(2) 0.0441(8) Uani 1 1 d . A .
C1 C -0.05283(16) -0.09038(17) 0.62794(18) 0.0187(6) Uani 1 1 d . . .
C2 C -0.12225(17) -0.11287(19) 0.6626(2) 0.0241(7) Uani 1 1 d . . .
H2 H -0.1375 -0.0878 0.7120 0.029 Uiso 1 1 calc R . .
C3 C -0.16730(18) -0.17368(19) 0.6207(2) 0.0256(7) Uani 1 1 d . . .
H3 H -0.2136 -0.1900 0.6427 0.031 Uiso 1 1 calc R . .
C4 C -0.14478(18) -0.21127(19) 0.5458(2) 0.0258(7) Uani 1 1 d . . .
H4 H -0.1767 -0.2517 0.5191 0.031 Uiso 1 1 calc R . .
C5 C -0.07647(18) -0.18974(19) 0.51070(19) 0.0238(6) Uani 1 1 d . . .
H5 H -0.0615 -0.2149 0.4612 0.029 Uiso 1 1 calc R . .
C6 C -0.03126(16) -0.12868(17) 0.55303(18) 0.0187(6) Uani 1 1 d . . .
C7 C 0.05950(16) -0.03670(16) 0.59983(18) 0.0165(6) Uani 1 1 d . . .
C8 C 0.13331(16) 0.00927(17) 0.60429(17) 0.0178(6) Uani 1 1 d . . .
C9 C 0.15771(16) 0.06585(17) 0.67077(18) 0.0177(6) Uani 1 1 d . . .
C10 C 0.23107(17) 0.10374(18) 0.66852(18) 0.0210(6) Uani 1 1 d . . .
H10 H 0.2478 0.1410 0.7116 0.025 Uiso 1 1 calc R . .
C11 C 0.27917(17) 0.08725(19) 0.6041(2) 0.0245(7) Uani 1 1 d . . .
H11 H 0.3278 0.1128 0.6048 0.029 Uiso 1 1 calc R . .
C12 C 0.25542(18) 0.03281(19) 0.5386(2) 0.0253(7) Uani 1 1 d . . .
H12 H 0.2875 0.0222 0.4948 0.030 Uiso 1 1 calc R . .
C13 C 0.18373(17) -0.00520(18) 0.53917(18) 0.0213(6) Uani 1 1 d . . .
H13 H 0.1679 -0.0417 0.4951 0.026 Uiso 1 1 calc R . .
C14 C 0.13891(16) 0.24373(18) 0.77459(17) 0.0186(6) Uani 1 1 d . . .
C15 C 0.08584(18) 0.26828(19) 0.70718(19) 0.0260(7) Uani 1 1 d . . .
H15 H 0.0493 0.2313 0.6820 0.031 Uiso 1 1 calc R . .
C16 C 0.0878(2) 0.34873(19) 0.6776(2) 0.0284(7) Uani 1 1 d . . .
H16 H 0.0527 0.3650 0.6318 0.034 Uiso 1 1 calc R . .
C17 C 0.14084(18) 0.40513(18) 0.71488(19) 0.0241(7) Uani 1 1 d . . .
C18 C 0.19325(17) 0.37956(19) 0.78350(19) 0.0234(7) Uani 1 1 d . . .
H18 H 0.2289 0.4170 0.8097 0.028 Uiso 1 1 calc R . .
C19 C 0.19296(16) 0.29929(18) 0.81308(19) 0.0203(6) Uani 1 1 d . . .
H19 H 0.2286 0.2827 0.8583 0.024 Uiso 1 1 calc R . .
C20 C 0.1411(2) 0.4922(2) 0.6816(2) 0.0340(8) Uani 1 1 d . . .
H20A H 0.1814 0.5230 0.7140 0.051 Uiso 1 1 calc R . .
H20B H 0.0910 0.5171 0.6877 0.051 Uiso 1 1 calc R . .
H20C H 0.1508 0.4918 0.6220 0.051 Uiso 1 1 calc R . .
C21 C 0.4991(2) 0.1217(3) 0.9056(3) 0.0554(12) Uani 1 1 d . . .
C22 C 0.4046(2) 0.2214(3) 0.8394(3) 0.0491(10) Uani 1 1 d . . .
H22A H 0.3591 0.2502 0.8551 0.074 Uiso 1 1 calc R A .
H22B H 0.3907 0.1882 0.7894 0.074 Uiso 1 1 calc R . .
H22C H 0.4441 0.2604 0.8268 0.074 Uiso 1 1 calc R . .
C23 C 0.3932(2) 0.1657(3) 0.9878(3) 0.0606(13) Uani 1 1 d . . .
H23A H 0.3494 0.2026 0.9809 0.091 Uiso 1 1 calc R A .
H23B H 0.4276 0.1819 1.0369 0.091 Uiso 1 1 calc R . .
H23C H 0.3747 0.1108 0.9961 0.091 Uiso 1 1 calc R . .
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'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
N1 Ni1 N1 99.48(14) . 2_556 ?
N1 Ni1 N3 91.13(9) . . ?
N1 Ni1 N3 112.53(9) 2_556 . ?
N1 Ni1 N3 112.53(9) . 2_556 ?
N1 Ni1 N3 91.13(9) 2_556 2_556 ?
N3 Ni1 N3 143.68(14) . 2_556 ?
O2 S1 O1 115.14(12) . . ?
O2 S1 N3 115.38(12) . . ?
O1 S1 N3 102.85(12) . . ?
O2 S1 C14 107.95(13) . . ?
O1 S1 C14 106.58(12) . . ?
N3 S1 C14 108.45(13) . . ?
C7 N1 C1 107.8(2) . . ?
C7 N1 Ni1 126.25(19) . . ?
C1 N1 Ni1 125.72(19) . . ?
C7 N2 C6 108.5(2) . . ?
C9 N3 S1 122.1(2) . . ?
C9 N3 Ni1 130.23(19) . . ?
S1 N3 Ni1 107.64(12) . . ?
C21 N4 C23 120.8(4) . . ?
C21 N4 C22 121.0(4) . . ?
C23 N4 C22 118.2(3) . . ?
N1 C1 C2 131.6(3) . . ?
N1 C1 C6 108.3(2) . . ?
C2 C1 C6 120.2(3) . . ?
C3 C2 C1 117.5(3) . . ?
C2 C3 C4 121.5(3) . . ?
C5 C4 C3 121.7(3) . . ?
C4 C5 C6 116.7(3) . . ?
N2 C6 C5 132.0(3) . . ?
N2 C6 C1 105.6(2) . . ?
C5 C6 C1 122.4(3) . . ?
N1 C7 N2 109.8(2) . . ?
N1 C7 C8 127.5(3) . . ?
N2 C7 C8 122.6(2) . . ?
C13 C8 C9 118.3(3) . . ?
C13 C8 C7 117.5(3) . . ?
C9 C8 C7 124.1(2) . . ?
C10 C9 N3 122.1(3) . . ?
C10 C9 C8 118.1(3) . . ?
N3 C9 C8 119.7(2) . . ?
C11 C10 C9 121.8(3) . . ?
C10 C11 C12 120.4(3) . . ?
C13 C12 C11 119.0(3) . . ?
C12 C13 C8 122.3(3) . . ?
C15 C14 C19 120.4(3) . . ?
C15 C14 S1 119.2(2) . . ?
C19 C14 S1 120.3(2) . . ?
C14 C15 C16 119.3(3) . . ?
C17 C16 C15 121.4(3) . . ?
C16 C17 C18 118.5(3) . . ?
C16 C17 C20 120.0(3) . . ?
C18 C17 C20 121.4(3) . . ?
C19 C18 C17 121.0(3) . . ?
C18 C19 C14 119.4(3) . . ?
O3B C21 N4 122.1(5) . . ?
O3B C21 O3A 120.7(5) . . ?
N4 C21 O3A 117.1(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 1.962(2) . ?
Ni1 N1 1.962(2) 2_556 ?
Ni1 N3 1.981(2) . ?
Ni1 N3 1.981(2) 2_556 ?
S1 O2 1.446(2) . ?
S1 O1 1.465(2) . ?
S1 N3 1.600(2) . ?
S1 C14 1.766(3) . ?
O3A C21 1.338(7) . ?
O3B C21 1.287(7) . ?
N1 C7 1.328(4) . ?
N1 C1 1.385(4) . ?
N2 C7 1.370(4) . ?
N2 C6 1.381(4) . ?
N3 C9 1.414(3) . ?
N4 C21 1.338(5) . ?
N4 C23 1.445(5) . ?
N4 C22 1.479(5) . ?
C1 C2 1.398(4) . ?
C1 C6 1.403(4) . ?
C2 C3 1.382(4) . ?
C3 C4 1.403(4) . ?
C4 C5 1.380(4) . ?
C5 C6 1.389(4) . ?
C7 C8 1.465(4) . ?
C8 C13 1.411(4) . ?
C8 C9 1.421(4) . ?
C9 C10 1.403(4) . ?
C10 C11 1.381(4) . ?
C11 C12 1.386(4) . ?
C12 C13 1.375(4) . ?
C14 C15 1.385(4) . ?
C14 C19 1.391(4) . ?
C15 C16 1.389(4) . ?
C16 C17 1.382(4) . ?
C17 C18 1.397(4) . ?
C17 C20 1.508(4) . ?
C18 C19 1.385(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
_geom_hbond_site_symmetry_A
N2 H2N O1 0.84(3) 2.08(3) 2.850(3) 153(3) 6
