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#$Date: 2016-03-21 19:19:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178845 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/99/4109998.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_4109998
loop_
_publ_author_name
'Sean A. Dalrymple'
'George K. H. Shimizu'
_publ_contact_author_address
;University of Calgary
2500 University Drive
Calgary Alberta
T2N 1N4
;
_publ_contact_author_email       gshimizu@ucalgary.ca
_publ_contact_author_name        G.K.H.Shimizu
_publ_section_title
;
 Crystal Engineering of a Permanently Porous Network Sustained Exclusively
 by Charge-Assisted Hydrogen Bonds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12114
_journal_page_last               12116
_journal_paper_doi               10.1021/ja076094v
_journal_volume                  129
_journal_year                    2007
_chemical_formula_moiety         'C10 H29.94 N6 Ni, 2(C8 H5 O3 S)'
_chemical_formula_sum            'C26 H39.94 N6 Ni O6 S2'
_chemical_formula_weight         655.41
_chemical_name_common            '[Ni(tame)2]1(PES)2'
_chemical_name_systematic
; 
 bis(1,1,1-tris(aminomethyl)ethane)nickel(II)di(2-phenylethynesulfonate) 
;
_space_group_IT_number           147
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      147
_symmetry_space_group_name_Hall  '-P 3'
_symmetry_space_group_name_H-M   'P -3'
_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                   13.862(5)
_cell_length_b                   13.862(5)
_cell_length_c                   13.784(5)
_cell_measurement_reflns_used    3488
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.39
_cell_volume                     2293.8(14)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6703
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.39
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_T_max  0.8869
_exptl_absorpt_correction_T_min  0.8402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick 2002)'
_exptl_crystal_colour            Purple
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1037.8
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0398
_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)+(0.0569P)²+0.0358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1127
_reflns_number_gt                2444
_reflns_number_total             3488
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja076094vsi20070817_075835.cif
_cod_data_source_block           import
_cod_database_code               4109998
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
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 0.3333 0.6667 0.01103(4) 0.0228(2) Uani 1 3 d S
N1 N 0.2118(2) 0.6688(3) -0.08021(18) 0.0279(5) Uani 1 1 d .
H1A H 0.1435 0.6098 -0.0630 0.033 Uiso 1 1 calc R
H1B H 0.2099 0.7329 -0.0674 0.033 Uiso 1 1 calc R
N2 N 0.2097(2) 0.54485(19) 0.10321(18) 0.0297(5) Uani 1 1 d .
H2A H 0.1426 0.5396 0.0880 0.036 Uiso 1 1 calc R
H2B H 0.2037 0.4772 0.0889 0.036 Uiso 1 1 calc R
C1 C 0.2252(3) 0.6630(4) -0.1863(2) 0.0328(7) Uani 1 1 d .
H1C H 0.2224 0.7260 -0.2173 0.039 Uiso 1 1 calc R
H1D H 0.1613 0.5933 -0.2110 0.039 Uiso 1 1 calc R
C2 C 0.3333 0.6667 -0.2173(4) 0.0301(10) Uani 1 3 d S
C3 C 0.3333 0.6667 -0.3299(4) 0.0388(12) Uani 1 3 d S
H3A H 0.2653 0.6015 -0.3536 0.058 Uiso 0.33 1 calc PR
H3B H 0.3985 0.6638 -0.3536 0.058 Uiso 0.33 1 calc PR
H3C H 0.3362 0.7347 -0.3536 0.058 Uiso 0.33 1 calc PR
C4 C 0.2266(3) 0.5627(3) 0.2086(2) 0.0443(8) Uani 1 1 d .
H4A H 0.2260 0.4969 0.2374 0.053 Uiso 1 1 calc R
H4B H 0.1625 0.5663 0.2360 0.053 Uiso 1 1 calc R
C5 C 0.3333 0.6667 0.2401(4) 0.0341(11) Uani 1 3 d S
C6 C 0.3333 0.6667 0.3525(4) 0.0502(14) Uani 1 3 d S
H6A H 0.4096 0.7137 0.3762 0.075 Uiso 0.33 1 calc PR
H6B H 0.3041 0.5904 0.3762 0.075 Uiso 0.33 1 calc PR
H6C H 0.2863 0.6959 0.3762 0.075 Uiso 0.33 1 calc PR
Ni2 Ni 0.0000 0.0000 0.0000 0.0227(3) Uani 1 6 d S
N3 N 0.0013(3) 0.1235(2) 0.0913(3) 0.0281(8) Uani 1 1 d .
H3D H 0.0616 0.1911 0.0746 0.034 Uiso 1 1 calc R
H3E H -0.0617 0.1275 0.0784 0.034 Uiso 1 1 calc R
C7 C 0.0060(4) 0.1085(3) 0.1974(4) 0.0399(11) Uani 1 1 d .
H7A H -0.0563 0.1127 0.2282 0.048 Uiso 1 1 calc R
H7B H 0.0761 0.1716 0.2225 0.048 Uiso 1 1 calc R
C8 C 0.0000 0.0000 0.2297(6) 0.0324(16) Uani 1 3 d S
C9 C 0.0000 0.0000 0.3401(7) 0.050(2) Uani 1 3 d S
H9A H -0.0554 0.0186 0.3638 0.076 Uiso 0.33 1 calc PR
H9B H 0.0740 0.0554 0.3638 0.076 Uiso 0.33 1 calc PR
H9C H -0.0186 -0.0740 0.3638 0.076 Uiso 0.33 1 calc PR
S1 S 0.33421(7) 0.33287(7) 0.12189(4) 0.02512(15) Uani 1 1 d .
O1 O 0.3312(2) 0.23179(17) 0.09013(14) 0.0368(5) Uani 1 1 d .
O2 O 0.23341(17) 0.3353(2) 0.10019(15) 0.0371(5) Uani 1 1 d .
O3 O 0.43489(18) 0.43349(18) 0.0951(2) 0.0361(6) Uani 1 1 d .
C10 C 0.3385(3) 0.3291(3) 0.24753(19) 0.0317(5) Uani 1 1 d .
C11 C 0.3385(3) 0.3261(3) 0.33379(18) 0.0342(6) Uani 1 1 d .
C12 C 0.3388(3) 0.3263(3) 0.43909(16) 0.0339(6) Uani 1 1 d .
C15 C 0.3349(3) 0.3263(3) 0.6406(2) 0.0447(7) Uani 1 1 d .
H15 H 0.3331 0.3264 0.7095 0.054 Uiso 1 1 calc R
C16 C 0.3059(3) 0.2296(3) 0.5907(2) 0.0507(10) Uani 1 1 d .
H16 H 0.2847 0.1628 0.6255 0.061 Uiso 1 1 calc R
C17 C 0.3072(3) 0.2288(3) 0.4906(2) 0.0456(9) Uani 1 1 d .
H17 H 0.2865 0.1614 0.4569 0.055 Uiso 1 1 calc R
C13 C 0.3681(3) 0.4231(3) 0.4894(2) 0.0491(9) Uani 1 1 d .
H13 H 0.3894 0.4903 0.4552 0.059 Uiso 1 1 calc R
C14 C 0.3665(3) 0.4224(3) 0.5898(2) 0.0522(10) Uani 1 1 d .
H14 H 0.3876 0.4896 0.6240 0.063 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'
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'
S S 0.1246 0.1234 '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'
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
N1 Ni1 N1 88.24(9) 2_665 3_565
N1 Ni1 N1 88.24(9) 2_665 .
N1 Ni1 N1 88.24(9) 3_565 .
N1 Ni1 N2 91.87(10) 2_665 .
N1 Ni1 N2 179.72(8) 3_565 .
N1 Ni1 N2 92.02(11) . .
N1 Ni1 N2 179.72(9) 2_665 3_565
N1 Ni1 N2 92.02(11) 3_565 3_565
N1 Ni1 N2 91.87(10) . 3_565
N2 Ni1 N2 87.87(9) . 3_565
N1 Ni1 N2 92.02(11) 2_665 2_665
N1 Ni1 N2 91.87(10) 3_565 2_665
N1 Ni1 N2 179.72(8) . 2_665
N2 Ni1 N2 87.87(9) . 2_665
N2 Ni1 N2 87.87(9) 3_565 2_665
C1 N1 Ni1 117.7(3) . .
C1 N1 H1A 107.9 . .
Ni1 N1 H1A 107.9 . .
C1 N1 H1B 107.9 . .
Ni1 N1 H1B 107.9 . .
H1A N1 H1B 107.2 . .
C4 N2 Ni1 117.36(15) . .
C4 N2 H2A 108.0 . .
Ni1 N2 H2A 108.0 . .
C4 N2 H2B 108.0 . .
Ni1 N2 H2B 108.0 . .
H2A N2 H2B 107.2 . .
N1 C1 C2 114.8(3) . .
N1 C1 H1C 108.6 . .
C2 C1 H1C 108.6 . .
N1 C1 H1D 108.6 . .
C2 C1 H1D 108.6 . .
H1C C1 H1D 107.5 . .
C1 C2 C1 112.56(18) 3_565 .
C1 C2 C1 112.56(18) 3_565 2_665
C1 C2 C1 112.56(18) . 2_665
C1 C2 C3 106.2(2) 3_565 .
C1 C2 C3 106.2(2) . .
C1 C2 C3 106.2(2) 2_665 .
C2 C3 H3A 109.5 . .
C2 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
C2 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
N2 C4 C5 116.0(3) . .
N2 C4 H4A 108.3 . .
C5 C4 H4A 108.3 . .
N2 C4 H4B 108.3 . .
C5 C4 H4B 108.3 . .
H4A C4 H4B 107.4 . .
C4 C5 C4 112.2(2) 2_665 .
C4 C5 C4 112.2(2) 2_665 3_565
C4 C5 C4 112.2(2) . 3_565
C4 C5 C6 106.6(2) 2_665 .
C4 C5 C6 106.6(2) . .
C4 C5 C6 106.6(2) 3_565 .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N3 Ni2 N3 88.28(13) 3 2
N3 Ni2 N3 88.28(13) 3 .
N3 Ni2 N3 88.28(13) 2 .
N3 Ni2 N3 91.72(13) 3 4
N3 Ni2 N3 91.72(13) 2 4
N3 Ni2 N3 180.0 . 4
N3 Ni2 N3 180.0 3 6
N3 Ni2 N3 91.72(13) 2 6
N3 Ni2 N3 91.72(13) . 6
N3 Ni2 N3 88.28(13) 4 6
N3 Ni2 N3 91.72(13) 3 5
N3 Ni2 N3 180.0 2 5
N3 Ni2 N3 91.72(13) . 5
N3 Ni2 N3 88.28(13) 4 5
N3 Ni2 N3 88.28(13) 6 5
C7 N3 Ni2 117.1(2) . .
C7 N3 H3D 108.0 . .
Ni2 N3 H3D 108.0 . .
C7 N3 H3E 108.0 . .
Ni2 N3 H3E 108.0 . .
H3D N3 H3E 107.3 . .
N3 C7 C8 116.1(4) . .
N3 C7 H7A 108.3 . .
C8 C7 H7A 108.3 . .
N3 C7 H7B 108.3 . .
C8 C7 H7B 108.3 . .
H7A C7 H7B 107.4 . .
C9 C8 C7 106.9(3) . 2
C9 C8 C7 106.9(3) . 3
C7 C8 C7 111.9(3) 2 3
C9 C8 C7 106.9(3) . .
C7 C8 C7 111.9(3) 2 .
C7 C8 C7 111.9(3) 3 .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
O3 S1 O2 113.80(10) . .
O3 S1 O1 113.83(11) . .
O2 S1 O1 113.51(14) . .
O3 S1 C10 104.7(2) . .
O2 S1 C10 104.81(13) . .
O1 S1 C10 104.91(13) . .
C11 C10 S1 178.1(3) . .
C10 C11 C12 178.0(4) . .
C13 C12 C17 119.0(2) . .
C13 C12 C11 120.3(3) . .
C17 C12 C11 120.7(3) . .
C14 C15 C16 119.2(3) . .
C14 C15 H15 120.4 . .
C16 C15 H15 120.4 . .
C15 C16 C17 120.6(3) . .
C15 C16 H16 119.7 . .
C17 C16 H16 119.7 . .
C16 C17 C12 120.1(3) . .
C16 C17 H17 119.9 . .
C12 C17 H17 119.9 . .
C12 C13 C14 120.0(3) . .
C12 C13 H13 120.0 . .
C14 C13 H13 120.0 . .
C15 C14 C13 121.0(3) . .
C15 C14 H14 119.5 . .
C13 C14 H14 119.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1 2.114(2) 2_665
Ni1 N1 2.114(2) 3_565
Ni1 N1 2.114(2) .
Ni1 N2 2.123(2) .
Ni1 N2 2.123(2) 3_565
Ni1 N2 2.123(2) 2_665
N1 C1 1.481(4) .
N1 H1A 0.9200 .
N1 H1B 0.9200 .
N2 C4 1.472(4) .
N2 H2A 0.9200 .
N2 H2B 0.9200 .
C1 C2 1.535(3) .
C1 H1C 0.9900 .
C1 H1D 0.9900 .
C2 C1 1.535(3) 3_565
C2 C1 1.535(3) 2_665
C2 C3 1.552(7) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C4 C5 1.524(3) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C4 1.524(3) 2_665
C5 C4 1.524(3) 3_565
C5 C6 1.550(8) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
Ni2 N3 2.118(3) 3
Ni2 N3 2.118(3) 2
Ni2 N3 2.118(3) .
Ni2 N3 2.118(3) 4
Ni2 N3 2.118(3) 6
Ni2 N3 2.118(3) 5
N3 C7 1.482(6) .
N3 H3D 0.9200 .
N3 H3E 0.9200 .
C7 C8 1.530(4) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.522(13) .
C8 C7 1.530(4) 2
C8 C7 1.530(4) 3
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
S1 O3 1.443(2) .
S1 O2 1.4455(18) .
S1 O1 1.4483(18) .
S1 C10 1.735(3) .
C10 C11 1.190(4) .
C11 C12 1.451(3) .
C12 C13 1.380(4) .
C12 C17 1.389(4) .
C15 C14 1.368(4) .
C15 C16 1.375(4) .
C15 H15 0.9500 .
C16 C17 1.380(4) .
C16 H16 0.9500 .
C17 H17 0.9500 .
C13 C14 1.384(4) .
C13 H13 0.9500 .
C14 H14 0.9500 .
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
N1 H1A O3 0.92 2.28 3.099(4) 148.7 6
N1 H1B O1 0.92 2.21 3.088(5) 159.0 5_565
N2 H2A O3 0.92 2.20 3.079(5) 160.2 3_565
N2 H2B O2 0.92 2.21 3.083(4) 158.5 .
N3 H3D O2 0.92 2.24 3.089(4) 152.5 .
N3 H3E O1 0.92 2.19 3.077(4) 160.6 2
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N1 Ni1 N1 C1 -41.3(3) 2_665 .
N1 Ni1 N1 C1 47.0(3) 3_565 .
N2 Ni1 N1 C1 -133.1(3) . .
N2 Ni1 N1 C1 139.0(3) 3_565 .
N1 Ni1 N2 C4 136.6(4) 2_665 .
N1 Ni1 N2 C4 -135.1(4) . .
N2 Ni1 N2 C4 -43.4(4) 3_565 .
N2 Ni1 N2 C4 44.6(4) 2_665 .
Ni1 N1 C1 C2 -5.2(5) . .
N1 C1 C2 C1 -61.0(4) . 3_565
N1 C1 C2 C1 67.5(4) . 2_665
N1 C1 C2 C3 -176.8(3) . .
Ni1 N2 C4 C5 -1.1(7) . .
N2 C4 C5 C4 -63.0(5) . 2_665
N2 C4 C5 C4 64.4(5) . 3_565
N2 C4 C5 C6 -179.3(4) . .
N3 Ni2 N3 C7 -41.6(3) 3 .
N3 Ni2 N3 C7 46.7(3) 2 .
N3 Ni2 N3 C7 138.4(3) 6 .
N3 Ni2 N3 C7 -133.3(3) 5 .
Ni2 N3 C7 C8 -4.7(5) . .
N3 C7 C8 C9 -177.1(3) . .
N3 C7 C8 C7 -60.3(5) . 2
N3 C7 C8 C7 66.2(5) . 3
C14 C15 C16 C17 -0.7(5) . .
C15 C16 C17 C12 0.4(5) . .
C13 C12 C17 C16 -0.3(5) . .
C11 C12 C17 C16 -178.8(3) . .
C17 C12 C13 C14 0.4(5) . .
C11 C12 C13 C14 179.0(3) . .
C16 C15 C14 C13 0.9(5) . .
C12 C13 C14 C15 -0.7(5) . .
