#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:10:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178692 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/03/4080390.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_4080390
loop_
_publ_author_name
'Brun, Sandra'
'Torres, Óscar'
'Pla-Quintana, Anna'
'Roglans, Anna'
'Goddard, Richard'
'Pörschke, Klaus-Richard'
_publ_section_title
;
 Nickel(0) Complexes of Acyclic Polyunsaturated Aza Ligands
;
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              1710
_journal_paper_doi               10.1021/om301160m
_journal_volume                  32
_journal_year                    2013
_chemical_compound_source        tetrahydrofuran
_chemical_formula_moiety         '2(C25 H32 N2 Ni O4 S2), C4 H8 O'
_chemical_formula_sum            'C54 H72 N4 Ni2 O9 S4'
_chemical_formula_weight         1166.82
_chemical_name_systematic
;
 N,N'-bis(4-tolylsulfonyl)-
 4,9-diazatrideca-1,6-diene-11-yne-nickel hemi-tetrahydrofuran solute
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                BMW-BB-238-01
_audit_creation_date             2011-10-25
_cell_angle_alpha                90.00
_cell_angle_beta                 105.413(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7565(18)
_cell_length_b                   15.921(3)
_cell_length_c                   16.427(3)
_cell_measurement_reflns_used    9725
_cell_measurement_temperature    100
_cell_measurement_theta_max      36.4109
_cell_measurement_theta_min      2.3439
_cell_volume                     2712.0(8)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (G. M. Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (G. M. Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0130
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            103280
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         36.51
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_T_max  0.92264
_exptl_absorpt_correction_T_min  0.84663
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.095
_refine_diff_density_max         3.688
_refine_diff_density_min         -1.011
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         13159
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0457
_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)+(0.0686P)²+2.8405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1323
_reflns_number_gt                11646
_reflns_number_total             13159
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om301160m_si_002.cif
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4080390
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.43702(14) 0.63957(10) 0.48654(9) 0.0213(2) Uani 1 1 d . . .
H1A H 0.4883 0.6159 0.5408 0.026 Uiso 1 1 calc R . .
H1B H 0.4562 0.6994 0.4787 0.026 Uiso 1 1 calc R . .
C2 C 0.30826(13) 0.61585(9) 0.46037(8) 0.0190(2) Uani 1 1 d . . .
H2A H 0.2812 0.5748 0.4984 0.023 Uiso 1 1 calc R . .
C3 C 0.20572(13) 0.67724(9) 0.41799(9) 0.0198(2) Uani 1 1 d . . .
H3A H 0.1758 0.7088 0.4611 0.024 Uiso 1 1 calc R . .
H3B H 0.2414 0.7179 0.3846 0.024 Uiso 1 1 calc R . .
C4 C 0.13168(12) 0.58973(9) 0.29145(8) 0.0181(2) Uani 1 1 d . . .
H4A H 0.1648 0.6321 0.2583 0.022 Uiso 1 1 calc R . .
H4B H 0.0537 0.5640 0.2537 0.022 Uiso 1 1 calc R . .
C5 C 0.23225(12) 0.52299(8) 0.32142(8) 0.01728(19) Uani 1 1 d . . .
H5 H 0.2021 0.4722 0.3465 0.021 Uiso 1 1 calc R . .
C6 C 0.31976(12) 0.50687(8) 0.27394(8) 0.0176(2) Uani 1 1 d . . .
H6 H 0.3075 0.5442 0.2235 0.021 Uiso 1 1 calc R . .
C7 C 0.36290(13) 0.41976(9) 0.25913(9) 0.0199(2) Uani 1 1 d . . .
H7A H 0.3768 0.3862 0.3115 0.024 Uiso 1 1 calc R . .
H7B H 0.2955 0.3918 0.2144 0.024 Uiso 1 1 calc R . .
C8 C 0.59582(13) 0.45746(10) 0.29844(9) 0.0214(2) Uani 1 1 d . . .
H8A H 0.6593 0.4805 0.2704 0.026 Uiso 1 1 calc R . .
H8B H 0.6376 0.4104 0.3349 0.026 Uiso 1 1 calc R . .
C9 C 0.56161(12) 0.52364(8) 0.35200(8) 0.0177(2) Uani 1 1 d . . .
C10 C 0.60070(12) 0.57683(8) 0.40925(8) 0.0181(2) Uani 1 1 d . . .
C11 C 0.70320(13) 0.62622(10) 0.46684(9) 0.0222(2) Uani 1 1 d . . .
H11A H 0.6882 0.6862 0.4545 0.033 Uiso 1 1 calc R . .
H11B H 0.7871 0.6101 0.4589 0.033 Uiso 1 1 calc R . .
H11C H 0.7023 0.6152 0.5254 0.033 Uiso 1 1 calc R . .
C12 C -0.02470(13) 0.75894(9) 0.26209(8) 0.0195(2) Uani 1 1 d . . .
C13 C -0.06046(15) 0.73973(9) 0.17608(9) 0.0219(2) Uani 1 1 d . . .
H13 H -0.1020 0.6881 0.1567 0.026 Uiso 1 1 calc R . .
C14 C -0.03428(15) 0.79744(9) 0.11924(9) 0.0215(2) Uani 1 1 d . . .
H14 H -0.0578 0.7848 0.0606 0.026 Uiso 1 1 calc R . .
C15 C 0.02623(13) 0.87386(9) 0.14723(8) 0.0191(2) Uani 1 1 d . . .
C16 C 0.06142(14) 0.89161(9) 0.23363(9) 0.0208(2) Uani 1 1 d . . .
H16 H 0.1026 0.9434 0.2532 0.025 Uiso 1 1 calc R . .
C17 C 0.03678(14) 0.83436(9) 0.29124(9) 0.0209(2) Uani 1 1 d . . .
H17 H 0.0616 0.8465 0.3500 0.025 Uiso 1 1 calc R . .
C18 C 0.05141(16) 0.93632(10) 0.08489(10) 0.0244(3) Uani 1 1 d . . .
H18A H 0.0528 0.9073 0.0325 0.037 Uiso 1 1 calc R . .
H18B H 0.1348 0.9636 0.1087 0.037 Uiso 1 1 calc R . .
H18C H -0.0170 0.9788 0.0728 0.037 Uiso 1 1 calc R . .
C19 C 0.54172(15) 0.26003(10) 0.25549(10) 0.0234(2) Uani 1 1 d . . .
C20 C 0.66438(15) 0.24711(10) 0.30969(10) 0.0241(2) Uani 1 1 d . . .
H20 H 0.7363 0.2777 0.3022 0.029 Uiso 1 1 calc R . .
C21 C 0.6798(2) 0.18900(11) 0.37454(11) 0.0311(3) Uani 1 1 d . . .
H21 H 0.7629 0.1799 0.4117 0.037 Uiso 1 1 calc R . .
C22 C 0.5738(3) 0.14348(12) 0.38579(13) 0.0379(4) Uani 1 1 d . . .
C23 C 0.4534(2) 0.15640(13) 0.32936(15) 0.0387(4) Uani 1 1 d . . .
H23 H 0.3817 0.1246 0.3356 0.046 Uiso 1 1 calc R . .
C24 C 0.43552(18) 0.21453(12) 0.26431(13) 0.0320(3) Uani 1 1 d . . .
H24 H 0.3527 0.2231 0.2266 0.038 Uiso 1 1 calc R . .
C25 C 0.5905(4) 0.08052(16) 0.45608(17) 0.0571(8) Uani 1 1 d . . .
H25A H 0.5788 0.0237 0.4323 0.086 Uiso 1 1 calc R . .
H25B H 0.5264 0.0910 0.4875 0.086 Uiso 1 1 calc R . .
H25C H 0.6773 0.0858 0.4942 0.086 Uiso 1 1 calc R . .
C26 C 0.0049(13) 0.4349(7) -0.0254(8) 0.112(4) Uiso 0.50 1 d PD A -2
H26A H 0.0587 0.4078 -0.0583 0.134 Uiso 0.50 1 calc PR A -2
H26B H -0.0535 0.3924 -0.0116 0.134 Uiso 0.50 1 calc PR A -2
C27 C 0.0956(9) 0.4790(6) 0.0613(6) 0.0732(11) Uiso 0.50 1 d PD A -2
H27A H 0.1355 0.4388 0.1067 0.088 Uiso 0.50 1 calc PR A -2
H27B H 0.1593 0.5199 0.0514 0.088 Uiso 0.50 1 calc PR A -2
C28 C -0.0359(11) 0.5198(8) 0.0697(7) 0.110(4) Uiso 0.50 1 d PD A -2
H28A H -0.0985 0.4753 0.0735 0.132 Uiso 0.50 1 calc PR A -2
H28B H -0.0200 0.5551 0.1210 0.132 Uiso 0.50 1 calc PR A -2
C29 C -0.0844(10) 0.5692(6) -0.0034(6) 0.082(2) Uiso 0.50 1 d PD A -2
H29A H -0.0326 0.6206 -0.0034 0.098 Uiso 0.50 1 calc PR A -2
H29B H -0.1761 0.5844 -0.0114 0.098 Uiso 0.50 1 calc PR A -2
N1 N 0.09645(11) 0.63183(8) 0.36210(7) 0.01874(19) Uani 1 1 d . . .
H1 H 0.0814 0.5877 0.3953 0.022 Uiso 1 1 calc R . .
N2 N 0.48389(12) 0.42474(8) 0.23325(8) 0.0209(2) Uani 1 1 d . . .
H2 H 0.4673 0.4669 0.1926 0.025 Uiso 1 1 calc R . .
Ni1 Ni 0.411112(16) 0.564346(11) 0.383497(10) 0.01513(4) Uani 1 1 d . . .
O1 O -0.13799(11) 0.62296(8) 0.29242(8) 0.0279(2) Uani 1 1 d . . .
O2 O -0.05613(13) 0.72417(9) 0.40969(8) 0.0293(2) Uani 1 1 d . . .
O3 O 0.40434(14) 0.32529(10) 0.11456(8) 0.0351(3) Uani 1 1 d . . .
O4 O 0.63718(13) 0.36035(9) 0.16302(8) 0.0292(2) Uani 1 1 d . . .
O5 O -0.0657(6) 0.5026(4) -0.0706(4) 0.0732(11) Uiso 0.50 1 d PD A -2
S1 S -0.04208(3) 0.68222(2) 0.33519(2) 0.02123(7) Uani 1 1 d . . .
S2 S 0.51717(4) 0.34258(3) 0.18181(2) 0.02373(7) Uani 1 1 d . . .
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'
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 1.00 0.0970
0.00 1.00 -1.00 0.0940
-1.00 3.00 2.00 0.0950
1.00 -3.00 -2.00 0.0920
3.00 0.00 -1.00 0.0400
-3.00 0.00 1.00 0.0550
0.00 1.00 2.00 0.1170
0.00 -1.00 -3.00 0.1070
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 C1 Ni1 71.16(8) y
C1 C2 C3 121.10(13) y
C1 C2 Ni1 69.13(8) y
C3 C2 Ni1 115.09(9) y
N1 C3 C2 109.62(12) y
N1 C4 C5 112.14(11) y
C6 C5 C4 118.70(11) y
C6 C5 Ni1 69.58(7) y
C4 C5 Ni1 115.99(9) y
C5 C6 C7 122.88(12) y
C5 C6 Ni1 70.16(8) y
C7 C6 Ni1 117.59(9) y
N2 C7 C6 109.33(12) y
N2 C8 C9 113.47(11) y
C10 C9 C8 147.21(13) y
C10 C9 Ni1 73.19(9) y
C8 C9 Ni1 138.94(10) y
C9 C10 C11 152.50(14) y
C9 C10 Ni1 69.54(8) y
C11 C10 Ni1 137.97(11) y
C17 C12 C13 120.98(12) y
C17 C12 S1 119.43(10) y
C13 C12 S1 119.24(11) y
C14 C13 C12 118.95(14) y
C13 C14 C15 120.89(13) y
C16 C15 C14 119.12(12) y
C16 C15 C18 120.61(14) y
C14 C15 C18 120.27(13) y
C17 C16 C15 120.67(14) y
C16 C17 C12 119.37(13) y
C24 C19 C20 121.27(17) y
C24 C19 S2 118.90(14) y
C20 C19 S2 119.49(12) y
C21 C20 C19 119.19(16) y
C20 C21 C22 120.62(19) y
C23 C22 C21 118.70(18) y
C23 C22 C25 120.7(2) y
C21 C22 C25 120.6(2) y
C24 C23 C22 121.65(18) y
C23 C24 C19 118.53(19) y
O5 C26 C27 104.0(8) y
C28 C27 C26 85.0(8) y
C29 C28 C27 106.8(9) y
C28 C29 O5 97.6(8) y
C3 N1 C4 112.58(10) y
C3 N1 S1 116.31(10) y
C4 N1 S1 114.45(9) y
C7 N2 C8 114.95(11) y
C7 N2 S2 115.71(10) y
C8 N2 S2 113.92(10) y
C9 Ni1 C10 37.27(6) y
C9 Ni1 C6 81.61(5) y
C10 Ni1 C6 117.66(6) y
C9 Ni1 C1 118.71(6) y
C10 Ni1 C1 81.80(6) y
C6 Ni1 C1 159.00(6) y
C9 Ni1 C5 120.28(6) y
C10 Ni1 C5 157.46(6) y
C6 Ni1 C5 40.26(5) y
C1 Ni1 C5 120.73(6) y
C9 Ni1 C2 157.06(6) y
C10 Ni1 C2 121.35(6) y
C6 Ni1 C2 120.83(6) y
C1 Ni1 C2 39.71(6) y
C5 Ni1 C2 81.11(6) y
C26 O5 C29 107.2(7) y
O1 S1 O2 119.83(8) y
O1 S1 N1 107.01(7) y
O2 S1 N1 106.88(7) y
O1 S1 C12 108.39(7) y
O2 S1 C12 108.26(7) y
N1 S1 C12 105.62(6) y
O4 S2 O3 119.90(8) y
O4 S2 N2 106.54(7) y
O3 S2 N2 107.03(8) y
O4 S2 C19 108.46(8) y
O3 S2 C19 109.17(9) y
N2 S2 C19 104.70(7) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.389(2) y
C1 Ni1 2.0313(14) y
C2 C3 1.4995(19) y
C2 Ni1 2.0576(13) y
C3 N1 1.4743(19) y
C4 N1 1.4743(18) y
C4 C5 1.5029(18) y
C5 C6 1.3966(19) y
C5 Ni1 2.0328(13) y
C6 C7 1.503(2) y
C6 Ni1 2.0253(13) y
C7 N2 1.4747(19) y
C8 N2 1.4772(19) y
C8 C9 1.481(2) y
C9 C10 1.2522(19) y
C9 Ni1 1.9374(13) y
C10 C11 1.4746(19) y
C10 Ni1 1.9796(13) y
C12 C17 1.393(2) y
C12 C13 1.396(2) y
C12 S1 1.7573(13) y
C13 C14 1.391(2) y
C14 C15 1.399(2) y
C15 C16 1.397(2) y
C15 C18 1.5028(19) y
C16 C17 1.389(2) y
C19 C24 1.392(2) y
C19 C20 1.397(2) y
C19 S2 1.7585(17) y
C20 C21 1.387(2) y
C21 C22 1.405(3) y
C22 C23 1.393(4) y
C22 C25 1.503(3) y
C23 C24 1.388(3) y
C26 O5 1.410(12) y
C26 C27 1.653(13) y
C27 C28 1.596(12) y
C28 C29 1.414(12) y
C29 O5 1.582(10) y
N1 S1 1.6460(12) y
N2 S2 1.6475(13) y
O1 S1 1.4362(14) y
O2 S1 1.4370(13) y
O3 S2 1.4340(13) y
O4 S2 1.4330(13) y
