#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:19:42 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179241 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/61/4316135.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_4316135
loop_
_publ_author_name
'Kate R. Edelman'
'Bradley J. Holliday'
_publ_section_title
;
 Metal-Interrupted Perylene Diimide: Toward a New Class of Tunable n-Type
 Inorganic-Organic Hybrid Semiconductors
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6787
_journal_page_last               6789
_journal_paper_doi               10.1021/ic100785r
_journal_volume                  49
_journal_year                    2010
_chemical_formula_moiety
'C51, H46, N4, Ni, O6', 'C3, H7, N, O', 'H2, O'
_chemical_formula_sum            'C54 H55 N5 Ni O8'
_chemical_formula_weight         960.734
_chemical_melting_point          347.6
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.225(2)
_cell_angle_beta                 94.799(3)
_cell_angle_gamma                104.624(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6700(4)
_cell_length_b                   14.0580(7)
_cell_length_c                   18.1070(10)
_cell_measurement_reflns_used    5724
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      1.0
_cell_volume                     2241.2(2)
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_data_reduction
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_molecular_graphics    'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1657
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7735
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.498
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.8856
_exptl_absorpt_process_details
;
(see. N.W. Alcock (1970). Cryst. Computing, p271)
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.925
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     574
_refine_ls_number_reflns         7735
_refine_ls_number_restraints     392
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.1727
_refine_ls_R_factor_gt           0.0816
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1086P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1909
_refine_ls_wR_factor_ref         0.2209
_reflns_number_gt                3838
_reflns_number_total             7735
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic100785r_si_002.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        2241.24(19)
_cod_database_code               4316135
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.29195(8) 0.01547(6) -0.02400(4) 0.0367(3) Uani 1 1 d U . .
O1 O -0.5242(5) -0.1954(4) 0.3926(2) 0.0536(12) Uani 1 1 d U . .
O2 O -0.1573(4) -0.2070(3) 0.5595(2) 0.0442(11) Uani 1 1 d U . .
O3 O 0.2623(4) 0.0805(3) 0.0757(2) 0.0373(10) Uani 1 1 d U . .
O4 O 0.4062(4) 0.1462(3) -0.0138(2) 0.0459(11) Uani 1 1 d U . .
O5 O 1.1766(7) 0.4066(4) -0.3545(3) 0.0925(19) Uani 1 1 d U . .
O6 O 1.4759(6) 0.5302(5) -0.1223(3) 0.0850(18) Uani 1 1 d U . .
N1 N -0.3415(5) -0.2034(4) 0.4758(3) 0.0371(12) Uani 1 1 d U . .
N2 N 0.1288(5) -0.1003(3) -0.0416(3) 0.0323(11) Uani 1 1 d U . .
N3 N 0.3708(5) -0.0523(4) -0.1086(3) 0.0349(12) Uani 1 1 d U . .
N4 N 1.3220(7) 0.4701(5) -0.2388(4) 0.0694(18) Uani 1 1 d U . .
C1 C -0.5459(8) -0.2278(6) 0.6429(4) 0.068(2) Uani 1 1 d DU . .
H1A H -0.6438 -0.2665 0.6134 0.103 Uiso 1 1 calc R . .
H1B H -0.5522 -0.1779 0.6925 0.103 Uiso 1 1 calc R . .
H1C H -0.4966 -0.2764 0.6536 0.103 Uiso 1 1 calc R . .
C2 C -0.5343(8) -0.0943(5) 0.5771(4) 0.064(2) Uani 1 1 d DU . .
H2A H -0.4794 -0.0593 0.5446 0.096 Uiso 1 1 calc R . .
H2B H -0.5379 -0.0425 0.6263 0.096 Uiso 1 1 calc R . .
H2C H -0.6331 -0.1323 0.5487 0.096 Uiso 1 1 calc R . .
C3 C -0.4610(6) -0.1697(4) 0.5949(3) 0.0409(16) Uani 1 1 d DU . .
H3 H -0.3619 -0.1296 0.6258 0.049 Uiso 1 1 calc R . .
C4 C -0.4461(7) -0.2473(5) 0.5204(3) 0.0463(17) Uani 1 1 d DU . .
H4A H -0.4159 -0.3032 0.5339 0.056 Uiso 1 1 calc R . .
H4B H -0.5424 -0.2795 0.4862 0.056 Uiso 1 1 calc R . .
C5 C -0.3962(7) -0.1841(5) 0.4092(3) 0.0369(15) Uani 1 1 d U . .
C6 C -0.2911(6) -0.1520(4) 0.3604(3) 0.0330(14) Uani 1 1 d U . .
C7 C -0.1402(6) -0.1275(4) 0.3865(3) 0.0313(14) Uani 1 1 d U . .
C8 C -0.0901(6) -0.1434(4) 0.4558(3) 0.0316(14) Uani 1 1 d U . .
C9 C -0.1953(7) -0.1877(5) 0.5018(3) 0.0385(15) Uani 1 1 d U . .
C10 C -0.3396(6) -0.1434(5) 0.2893(3) 0.0384(15) Uani 1 1 d U . .
H10 H -0.4407 -0.1614 0.2706 0.046 Uiso 1 1 calc R . .
C11 C -0.2391(6) -0.1079(5) 0.2448(3) 0.0380(15) Uani 1 1 d U . .
H11 H -0.2742 -0.1043 0.1954 0.046 Uiso 1 1 calc R . .
C12 C -0.0934(6) -0.0786(4) 0.2695(3) 0.0298(13) Uani 1 1 d U . .
C13 C -0.0383(6) -0.0889(4) 0.3418(3) 0.0324(14) Uani 1 1 d U . .
C14 C 0.1109(6) -0.0688(5) 0.3700(3) 0.0367(15) Uani 1 1 d U . .
H14 H 0.1807 -0.0444 0.3408 0.044 Uiso 1 1 calc R . .
C15 C 0.1568(6) -0.0837(5) 0.4378(3) 0.0391(15) Uani 1 1 d U . .
H15 H 0.2577 -0.0686 0.4555 0.047 Uiso 1 1 calc R . .
C16 C 0.0568(6) -0.1211(5) 0.4816(3) 0.0392(15) Uani 1 1 d U . .
H16 H 0.0898 -0.1312 0.5289 0.047 Uiso 1 1 calc R . .
C17 C 0.0041(6) -0.0400(5) 0.2185(3) 0.0319(14) Uani 1 1 d U . .
C18 C -0.0165(6) -0.0940(5) 0.1385(3) 0.0316(14) Uani 1 1 d U . .
H18 H -0.0927 -0.1573 0.1166 0.038 Uiso 1 1 calc R . .
C19 C 0.0727(6) -0.0574(4) 0.0892(3) 0.0304(13) Uani 1 1 d U . .
C20 C 0.1819(6) 0.0377(5) 0.1193(3) 0.0324(14) Uani 1 1 d U . .
C21 C 0.2020(6) 0.0940(5) 0.2015(3) 0.0345(14) Uani 1 1 d U . .
H21 H 0.2751 0.1588 0.2235 0.041 Uiso 1 1 calc R . .
C22 C 0.1160(6) 0.0544(5) 0.2486(3) 0.0344(14) Uani 1 1 d U . .
H22 H 0.1327 0.0921 0.3031 0.041 Uiso 1 1 calc R . .
C23 C 0.0455(6) -0.1165(4) 0.0072(3) 0.0312(13) Uani 1 1 d U . .
H23 H -0.0417 -0.1722 -0.0124 0.037 Uiso 1 1 calc R . .
C24 C 0.0766(6) -0.1598(4) -0.1264(3) 0.0327(14) Uani 1 1 d U . .
H24A H 0.0688 -0.1103 -0.1546 0.039 Uiso 1 1 calc R . .
H24B H -0.0218 -0.2073 -0.1329 0.039 Uiso 1 1 calc R . .
C25 C 0.1737(6) -0.2235(4) -0.1644(3) 0.0358(14) Uani 1 1 d U . .
C26 C 0.3333(6) -0.1653(5) -0.1296(4) 0.0400(15) Uani 1 1 d U . .
H26A H 0.3587 -0.1826 -0.0820 0.048 Uiso 1 1 calc R . .
H26B H 0.3936 -0.1911 -0.1680 0.048 Uiso 1 1 calc R . .
C27 C 0.1392(7) -0.3287(5) -0.1497(4) 0.0554(19) Uani 1 1 d U . .
H27A H 0.1450 -0.3168 -0.0933 0.083 Uiso 1 1 calc R . .
H27B H 0.2095 -0.3651 -0.1696 0.083 Uiso 1 1 calc R . .
H27C H 0.0412 -0.3712 -0.1770 0.083 Uiso 1 1 calc R . .
C28 C 0.1427(7) -0.2421(6) -0.2526(3) 0.0544(19) Uani 1 1 d U . .
H28A H 0.0391 -0.2766 -0.2725 0.082 Uiso 1 1 calc R . .
H28B H 0.1991 -0.2863 -0.2797 0.082 Uiso 1 1 calc R . .
H28C H 0.1701 -0.1752 -0.2621 0.082 Uiso 1 1 calc R . .
C29 C 0.4764(6) -0.0070(5) -0.1381(3) 0.0329(14) Uani 1 1 d U . .
H29 H 0.5151 -0.0511 -0.1759 0.039 Uiso 1 1 calc R . .
C30 C 0.5394(6) 0.1024(4) -0.1189(3) 0.0295(13) Uani 1 1 d U . .
C31 C 0.6530(6) 0.1404(5) -0.1580(3) 0.0375(15) Uani 1 1 d U . .
H31 H 0.6828 0.0915 -0.1971 0.045 Uiso 1 1 calc R . .
C32 C 0.7199(6) 0.2438(5) -0.1412(3) 0.0403(15) Uani 1 1 d U . .
C33 C 0.6729(7) 0.3146(5) -0.0818(4) 0.0475(17) Uani 1 1 d U . .
H33 H 0.7160 0.3873 -0.0695 0.057 Uiso 1 1 calc R . .
C34 C 0.5676(7) 0.2808(5) -0.0422(4) 0.0489(17) Uani 1 1 d U . .
H34 H 0.5390 0.3305 -0.0032 0.059 Uiso 1 1 calc R . .
C35 C 0.4998(6) 0.1737(5) -0.0575(3) 0.0385(15) Uani 1 1 d U . .
C36 C 0.8433(6) 0.2853(5) -0.1791(3) 0.0391(15) Uani 1 1 d U . .
C37 C 0.8219(7) 0.2769(5) -0.2578(4) 0.0460(16) Uani 1 1 d U . .
H37 H 0.7285 0.2428 -0.2892 0.055 Uiso 1 1 calc R . .
C38 C 0.9368(8) 0.3182(5) -0.2904(4) 0.0555(19) Uani 1 1 d U . .
H38 H 0.9206 0.3117 -0.3444 0.067 Uiso 1 1 calc R . .
C39 C 1.0719(7) 0.3678(5) -0.2480(4) 0.0481(17) Uani 1 1 d U . .
C40 C 1.0985(7) 0.3764(4) -0.1694(4) 0.0405(16) Uani 1 1 d U . .
C41 C 1.2350(7) 0.4254(5) -0.1252(4) 0.0493(17) Uani 1 1 d U . .
C42 C 1.2637(7) 0.4319(5) -0.0477(4) 0.0541(18) Uani 1 1 d U . .
H42 H 1.3597 0.4636 -0.0192 0.065 Uiso 1 1 calc R . .
C43 C 1.1507(7) 0.3917(5) -0.0103(4) 0.0521(18) Uani 1 1 d U . .
H43 H 1.1696 0.3959 0.0431 0.062 Uiso 1 1 calc R . .
C44 C 1.0145(7) 0.3469(4) -0.0531(3) 0.0389(15) Uani 1 1 d U . .
H44 H 0.9381 0.3215 -0.0278 0.047 Uiso 1 1 calc R . .
C45 C 0.9811(6) 0.3364(4) -0.1326(3) 0.0353(14) Uani 1 1 d U . .
C46 C 1.1906(9) 0.4127(6) -0.2854(4) 0.068(2) Uani 1 1 d U . .
C47 C 1.3549(8) 0.4782(7) -0.1590(5) 0.071(2) Uani 1 1 d U . .
C48 C 1.4296(8) 0.5331(6) -0.2745(4) 0.074(2) Uani 1 1 d DU . .
H48A H 1.3772 0.5607 -0.3087 0.089 Uiso 1 1 calc R . .
H48B H 1.4971 0.5930 -0.2321 0.089 Uiso 1 1 calc R . .
C49 C 1.5149(9) 0.4696(7) -0.3217(5) 0.088(3) Uani 1 1 d DU . .
H49 H 1.4471 0.4044 -0.3604 0.105 Uiso 1 1 calc R . .
C50 C 1.6044(12) 0.5342(9) -0.3653(7) 0.142(4) Uani 1 1 d DU . .
H50A H 1.5416 0.5627 -0.3925 0.214 Uiso 1 1 calc R . .
H50B H 1.6469 0.4900 -0.4037 0.214 Uiso 1 1 calc R . .
H50C H 1.6820 0.5915 -0.3276 0.214 Uiso 1 1 calc R . .
C51 C 1.6147(11) 0.4421(8) -0.2678(6) 0.122(4) Uani 1 1 d DU . .
H51A H 1.6946 0.5043 -0.2382 0.183 Uiso 1 1 calc R . .
H51B H 1.6540 0.3885 -0.2991 0.183 Uiso 1 1 calc R . .
H51C H 1.5603 0.4156 -0.2312 0.183 Uiso 1 1 calc R . .
O1W O 0.2853(6) 0.2920(5) 0.1181(3) 0.0881(18) Uani 1 1 d U . .
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'
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
O4 Ni1 O3 83.60(17) . . ?
O4 Ni1 N3 94.37(19) . . ?
O3 Ni1 N3 163.24(19) . . ?
O4 Ni1 N2 162.0(2) . . ?
O3 Ni1 N2 92.89(18) . . ?
N3 Ni1 N2 93.91(19) . . ?
C20 O3 Ni1 127.4(4) . . ?
C35 O4 Ni1 128.7(4) . . ?
C9 N1 C5 124.9(5) . . ?
C9 N1 C4 117.0(5) . . ?
C5 N1 C4 118.1(5) . . ?
C23 N2 C24 118.7(5) . . ?
C23 N2 Ni1 126.8(4) . . ?
C24 N2 Ni1 112.4(3) . . ?
C29 N3 C26 117.4(5) . . ?
C29 N3 Ni1 125.3(4) . . ?
C26 N3 Ni1 115.7(4) . . ?
C46 N4 C47 123.3(6) . . ?
C46 N4 C48 116.6(6) . . ?
C47 N4 C48 120.0(6) . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C2 111.0(5) . . ?
C4 C3 C1 109.0(4) . . ?
C2 C3 C1 110.8(5) . . ?
C4 C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
C1 C3 H3 108.7 . . ?
N1 C4 C3 114.6(5) . . ?
N1 C4 H4A 108.6 . . ?
C3 C4 H4A 108.6 . . ?
N1 C4 H4B 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
O1 C5 N1 120.8(5) . . ?
O1 C5 C6 122.2(5) . . ?
N1 C5 C6 117.0(5) . . ?
C10 C6 C7 119.5(5) . . ?
C10 C6 C5 120.0(5) . . ?
C7 C6 C5 120.6(5) . . ?
C8 C7 C6 119.9(5) . . ?
C8 C7 C13 119.7(5) . . ?
C6 C7 C13 120.4(5) . . ?
C16 C8 C7 120.7(5) . . ?
C16 C8 C9 118.8(5) . . ?
C7 C8 C9 120.5(5) . . ?
O2 C9 N1 120.7(5) . . ?
O2 C9 C8 122.7(6) . . ?
N1 C9 C8 116.5(5) . . ?
C6 C10 C11 119.8(5) . . ?
C6 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 122.6(5) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12 C13 119.5(5) . . ?
C11 C12 C17 118.4(5) . . ?
C13 C12 C17 122.1(5) . . ?
C14 C13 C7 117.5(5) . . ?
C14 C13 C12 124.3(5) . . ?
C7 C13 C12 118.1(5) . . ?
C15 C14 C13 121.7(5) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C16 120.7(6) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C8 C16 C15 119.7(5) . . ?
C8 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C22 117.6(5) . . ?
C18 C17 C12 121.0(5) . . ?
C22 C17 C12 121.3(5) . . ?
C17 C18 C19 121.7(5) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C20 C19 C18 120.2(5) . . ?
C20 C19 C23 120.7(5) . . ?
C18 C19 C23 119.0(5) . . ?
O3 C20 C19 123.6(5) . . ?
O3 C20 C21 118.3(5) . . ?
C19 C20 C21 118.0(5) . . ?
C22 C21 C20 120.3(6) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C17 122.1(5) . . ?
C21 C22 H22 119.0 . . ?
C17 C22 H22 119.0 . . ?
N2 C23 C19 125.3(5) . . ?
N2 C23 H23 117.3 . . ?
C19 C23 H23 117.3 . . ?
N2 C24 C25 114.2(4) . . ?
N2 C24 H24A 108.7 . . ?
C25 C24 H24A 108.7 . . ?
N2 C24 H24B 108.7 . . ?
C25 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C24 C25 C28 106.9(5) . . ?
C24 C25 C26 110.3(4) . . ?
C28 C25 C26 111.6(5) . . ?
C24 C25 C27 110.8(4) . . ?
C28 C25 C27 109.6(5) . . ?
C26 C25 C27 107.7(5) . . ?
N3 C26 C25 115.1(5) . . ?
N3 C26 H26A 108.5 . . ?
C25 C26 H26A 108.5 . . ?
N3 C26 H26B 108.5 . . ?
C25 C26 H26B 108.5 . . ?
H26A C26 H26B 107.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C29 C30 126.2(5) . . ?
N3 C29 H29 116.9 . . ?
C30 C29 H29 116.9 . . ?
C35 C30 C29 120.9(5) . . ?
C35 C30 C31 119.4(5) . . ?
C29 C30 C31 119.6(5) . . ?
C32 C31 C30 122.5(5) . . ?
C32 C31 H31 118.8 . . ?
C30 C31 H31 118.8 . . ?
C31 C32 C33 117.2(5) . . ?
C31 C32 C36 123.4(5) . . ?
C33 C32 C36 119.4(6) . . ?
C34 C33 C32 121.7(6) . . ?
C34 C33 H33 119.2 . . ?
C32 C33 H33 119.2 . . ?
C33 C34 C35 121.9(6) . . ?
C33 C34 H34 119.1 . . ?
C35 C34 H34 119.1 . . ?
O4 C35 C30 123.9(5) . . ?
O4 C35 C34 118.8(5) . . ?
C30 C35 C34 117.3(5) . . ?
C37 C36 C45 120.1(5) . . ?
C37 C36 C32 121.3(6) . . ?
C45 C36 C32 118.6(5) . . ?
C38 C37 C36 119.8(6) . . ?
C38 C37 H37 120.1 . . ?
C36 C37 H37 120.1 . . ?
C39 C38 C37 122.3(6) . . ?
C39 C38 H38 118.8 . . ?
C37 C38 H38 118.8 . . ?
C38 C39 C40 119.7(6) . . ?
C38 C39 C46 120.2(6) . . ?
C40 C39 C46 120.1(6) . . ?
C41 C40 C39 121.0(6) . . ?
C41 C40 C45 119.1(6) . . ?
C39 C40 C45 119.8(6) . . ?
C42 C41 C40 121.6(6) . . ?
C42 C41 C47 117.9(6) . . ?
C40 C41 C47 120.4(6) . . ?
C41 C42 C43 120.4(6) . . ?
C41 C42 H42 119.8 . . ?
C43 C42 H42 119.8 . . ?
C44 C43 C42 118.1(6) . . ?
C44 C43 H43 120.9 . . ?
C42 C43 H43 120.9 . . ?
C43 C44 C45 123.3(6) . . ?
C43 C44 H44 118.3 . . ?
C45 C44 H44 118.3 . . ?
C44 C45 C36 124.4(5) . . ?
C44 C45 C40 117.4(5) . . ?
C36 C45 C40 118.1(5) . . ?
O5 C46 N4 117.8(7) . . ?
O5 C46 C39 124.0(7) . . ?
N4 C46 C39 118.1(6) . . ?
O6 C47 N4 118.6(7) . . ?
O6 C47 C41 124.7(7) . . ?
N4 C47 C41 116.6(7) . . ?
C49 C48 N4 111.9(6) . . ?
C49 C48 H48A 109.2 . . ?
N4 C48 H48A 109.2 . . ?
C49 C48 H48B 109.2 . . ?
N4 C48 H48B 109.2 . . ?
H48A C48 H48B 107.9 . . ?
C48 C49 C51 109.8(6) . . ?
C48 C49 C50 108.3(6) . . ?
C51 C49 C50 109.8(7) . . ?
C48 C49 H49 109.6 . . ?
C51 C49 H49 109.6 . . ?
C50 C49 H49 109.6 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C49 C51 H51A 109.5 . . ?
C49 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C49 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
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 O4 1.836(4) . ?
Ni1 O3 1.849(4) . ?
Ni1 N3 1.880(4) . ?
Ni1 N2 1.885(4) . ?
O1 C5 1.208(7) . ?
O2 C9 1.207(7) . ?
O3 C20 1.318(6) . ?
O4 C35 1.311(6) . ?
O5 C46 1.222(8) . ?
O6 C47 1.223(8) . ?
N1 C9 1.393(8) . ?
N1 C5 1.403(7) . ?
N1 C4 1.474(7) . ?
N2 C23 1.274(6) . ?
N2 C24 1.487(6) . ?
N3 C29 1.303(7) . ?
N3 C26 1.459(7) . ?
N4 C46 1.370(9) . ?
N4 C47 1.417(10) . ?
N4 C48 1.507(9) . ?
C1 C3 1.516(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.507(7) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.506(7) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.473(8) . ?
C6 C10 1.383(8) . ?
C6 C7 1.416(8) . ?
C7 C8 1.408(8) . ?
C7 C13 1.429(8) . ?
C8 C16 1.383(8) . ?
C8 C9 1.498(8) . ?
C10 C11 1.403(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.358(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.434(8) . ?
C12 C17 1.490(7) . ?
C13 C14 1.417(8) . ?
C14 C15 1.362(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.400(8) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.393(8) . ?
C17 C22 1.405(8) . ?
C18 C19 1.408(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.399(8) . ?
C19 C23 1.435(7) . ?
C20 C21 1.432(8) . ?
C21 C22 1.377(8) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.525(7) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C28 1.529(8) . ?
C25 C26 1.531(8) . ?
C25 C27 1.539(9) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.426(8) . ?
C29 H29 0.9500 . ?
C30 C35 1.411(8) . ?
C30 C31 1.431(8) . ?
C31 C32 1.362(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.425(8) . ?
C32 C36 1.503(8) . ?
C33 C34 1.362(8) . ?
C33 H33 0.9500 . ?
C34 C35 1.413(9) . ?
C34 H34 0.9500 . ?
C36 C37 1.388(8) . ?
C36 C45 1.405(8) . ?
C37 C38 1.380(9) . ?
C37 H37 0.9500 . ?
C38 C39 1.355(9) . ?
C38 H38 0.9500 . ?
C39 C40 1.388(9) . ?
C39 C46 1.480(9) . ?
C40 C41 1.377(9) . ?
C40 C45 1.441(8) . ?
C41 C42 1.377(9) . ?
C41 C47 1.492(10) . ?
C42 C43 1.418(9) . ?
C42 H42 0.9500 . ?
C43 C44 1.362(9) . ?
C43 H43 0.9500 . ?
C44 C45 1.403(8) . ?
C44 H44 0.9500 . ?
C48 C49 1.498(8) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 C51 1.512(8) . ?
C49 C50 1.530(8) . ?
C49 H49 1.0000 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 Ni1 O3 C20 179.9(5) . . . . ?
N3 Ni1 O3 C20 -96.2(8) . . . . ?
N2 Ni1 O3 C20 17.7(5) . . . . ?
O3 Ni1 O4 C35 167.2(5) . . . . ?
N3 Ni1 O4 C35 3.9(5) . . . . ?
N2 Ni1 O4 C35 -113.2(7) . . . . ?
O4 Ni1 N2 C23 -81.4(8) . . . . ?
O3 Ni1 N2 C23 -3.2(5) . . . . ?
N3 Ni1 N2 C23 161.4(5) . . . . ?
O4 Ni1 N2 C24 81.7(7) . . . . ?
O3 Ni1 N2 C24 159.9(4) . . . . ?
N3 Ni1 N2 C24 -35.5(4) . . . . ?
O4 Ni1 N3 C29 3.1(5) . . . . ?
O3 Ni1 N3 C29 -79.2(9) . . . . ?
N2 Ni1 N3 C29 167.1(5) . . . . ?
O4 Ni1 N3 C26 168.1(4) . . . . ?
O3 Ni1 N3 C26 85.8(8) . . . . ?
N2 Ni1 N3 C26 -27.9(4) . . . . ?
C9 N1 C4 C3 80.1(6) . . . . ?
C5 N1 C4 C3 -102.2(6) . . . . ?
C2 C3 C4 N1 69.4(7) . . . . ?
C1 C3 C4 N1 -168.3(5) . . . . ?
C9 N1 C5 O1 -176.6(6) . . . . ?
C4 N1 C5 O1 5.9(8) . . . . ?
C9 N1 C5 C6 4.5(8) . . . . ?
C4 N1 C5 C6 -173.0(5) . . . . ?
O1 C5 C6 C10 -6.2(9) . . . . ?
N1 C5 C6 C10 172.6(5) . . . . ?
O1 C5 C6 C7 172.3(6) . . . . ?
N1 C5 C6 C7 -8.8(8) . . . . ?
C10 C6 C7 C8 -175.2(5) . . . . ?
C5 C6 C7 C8 6.2(8) . . . . ?
C10 C6 C7 C13 3.3(8) . . . . ?
C5 C6 C7 C13 -175.3(5) . . . . ?
C6 C7 C8 C16 179.2(5) . . . . ?
C13 C7 C8 C16 0.7(8) . . . . ?
C6 C7 C8 C9 0.9(8) . . . . ?
C13 C7 C8 C9 -177.7(5) . . . . ?
C5 N1 C9 O2 -179.4(5) . . . . ?
C4 N1 C9 O2 -1.8(8) . . . . ?
C5 N1 C9 C8 2.2(8) . . . . ?
C4 N1 C9 C8 179.7(4) . . . . ?
C16 C8 C9 O2 -1.8(8) . . . . ?
C7 C8 C9 O2 176.5(5) . . . . ?
C16 C8 C9 N1 176.6(5) . . . . ?
C7 C8 C9 N1 -5.1(7) . . . . ?
C7 C6 C10 C11 -1.7(9) . . . . ?
C5 C6 C10 C11 176.9(6) . . . . ?
C6 C10 C11 C12 -1.7(9) . . . . ?
C10 C11 C12 C13 3.4(9) . . . . ?
C10 C11 C12 C17 -178.7(5) . . . . ?
C8 C7 C13 C14 0.4(8) . . . . ?
C6 C7 C13 C14 -178.2(5) . . . . ?
C8 C7 C13 C12 176.9(5) . . . . ?
C6 C7 C13 C12 -1.6(8) . . . . ?
C11 C12 C13 C14 174.6(6) . . . . ?
C17 C12 C13 C14 -3.2(9) . . . . ?
C11 C12 C13 C7 -1.7(8) . . . . ?
C17 C12 C13 C7 -179.4(5) . . . . ?
C7 C13 C14 C15 -1.2(9) . . . . ?
C12 C13 C14 C15 -177.5(5) . . . . ?
C13 C14 C15 C16 1.0(9) . . . . ?
C7 C8 C16 C15 -0.9(9) . . . . ?
C9 C8 C16 C15 177.4(5) . . . . ?
C14 C15 C16 C8 0.1(9) . . . . ?
C11 C12 C17 C18 -47.7(8) . . . . ?
C13 C12 C17 C18 130.1(6) . . . . ?
C11 C12 C17 C22 129.4(6) . . . . ?
C13 C12 C17 C22 -52.8(8) . . . . ?
C22 C17 C18 C19 1.3(8) . . . . ?
C12 C17 C18 C19 178.5(5) . . . . ?
C17 C18 C19 C20 -2.7(8) . . . . ?
C17 C18 C19 C23 -179.8(5) . . . . ?
Ni1 O3 C20 C19 -19.2(8) . . . . ?
Ni1 O3 C20 C21 164.1(4) . . . . ?
C18 C19 C20 O3 -174.9(5) . . . . ?
C23 C19 C20 O3 2.2(8) . . . . ?
C18 C19 C20 C21 1.9(8) . . . . ?
C23 C19 C20 C21 178.9(5) . . . . ?
O3 C20 C21 C22 177.1(5) . . . . ?
C19 C20 C21 C22 0.2(8) . . . . ?
C20 C21 C22 C17 -1.5(8) . . . . ?
C18 C17 C22 C21 0.8(8) . . . . ?
C12 C17 C22 C21 -176.4(5) . . . . ?
C24 N2 C23 C19 -172.4(5) . . . . ?
Ni1 N2 C23 C19 -10.3(8) . . . . ?
C20 C19 C23 N2 13.1(9) . . . . ?
C18 C19 C23 N2 -169.8(5) . . . . ?
C23 N2 C24 C25 -122.4(5) . . . . ?
Ni1 N2 C24 C25 73.0(5) . . . . ?
N2 C24 C25 C28 -157.6(5) . . . . ?
N2 C24 C25 C26 -36.1(6) . . . . ?
N2 C24 C25 C27 83.1(6) . . . . ?
C29 N3 C26 C25 -125.8(5) . . . . ?
Ni1 N3 C26 C25 68.0(6) . . . . ?
C24 C25 C26 N3 -34.8(7) . . . . ?
C28 C25 C26 N3 83.8(6) . . . . ?
C27 C25 C26 N3 -155.8(5) . . . . ?
C26 N3 C29 C30 -173.2(5) . . . . ?
Ni1 N3 C29 C30 -8.4(8) . . . . ?
N3 C29 C30 C35 6.8(9) . . . . ?
N3 C29 C30 C31 -178.5(5) . . . . ?
C35 C30 C31 C32 -3.7(9) . . . . ?
C29 C30 C31 C32 -178.5(5) . . . . ?
C30 C31 C32 C33 0.4(9) . . . . ?
C30 C31 C32 C36 177.5(5) . . . . ?
C31 C32 C33 C34 1.3(10) . . . . ?
C36 C32 C33 C34 -175.9(6) . . . . ?
C32 C33 C34 C35 0.3(10) . . . . ?
Ni1 O4 C35 C30 -6.0(9) . . . . ?
Ni1 O4 C35 C34 175.0(4) . . . . ?
C29 C30 C35 O4 0.8(9) . . . . ?
C31 C30 C35 O4 -173.9(5) . . . . ?
C29 C30 C35 C34 179.8(5) . . . . ?
C31 C30 C35 C34 5.1(8) . . . . ?
C33 C34 C35 O4 175.6(6) . . . . ?
C33 C34 C35 C30 -3.5(10) . . . . ?
C31 C32 C36 C37 69.3(8) . . . . ?
C33 C32 C36 C37 -113.7(7) . . . . ?
C31 C32 C36 C45 -112.9(7) . . . . ?
C33 C32 C36 C45 64.1(8) . . . . ?
C45 C36 C37 C38 0.6(9) . . . . ?
C32 C36 C37 C38 178.3(6) . . . . ?
C36 C37 C38 C39 -0.2(10) . . . . ?
C37 C38 C39 C40 1.3(10) . . . . ?
C37 C38 C39 C46 -178.7(7) . . . . ?
C38 C39 C40 C41 179.3(6) . . . . ?
C46 C39 C40 C41 -0.7(10) . . . . ?
C38 C39 C40 C45 -2.6(9) . . . . ?
C46 C39 C40 C45 177.4(6) . . . . ?
C39 C40 C41 C42 -178.2(6) . . . . ?
C45 C40 C41 C42 3.6(9) . . . . ?
C39 C40 C41 C47 5.2(10) . . . . ?
C45 C40 C41 C47 -173.0(6) . . . . ?
C40 C41 C42 C43 -2.6(10) . . . . ?
C47 C41 C42 C43 174.1(6) . . . . ?
C41 C42 C43 C44 0.0(10) . . . . ?
C42 C43 C44 C45 1.6(9) . . . . ?
C43 C44 C45 C36 176.2(6) . . . . ?
C43 C44 C45 C40 -0.5(9) . . . . ?
C37 C36 C45 C44 -178.5(6) . . . . ?
C32 C36 C45 C44 3.7(9) . . . . ?
C37 C36 C45 C40 -1.8(8) . . . . ?
C32 C36 C45 C40 -179.6(5) . . . . ?
C41 C40 C45 C44 -2.1(8) . . . . ?
C39 C40 C45 C44 179.8(5) . . . . ?
C41 C40 C45 C36 -179.0(6) . . . . ?
C39 C40 C45 C36 2.9(8) . . . . ?
C47 N4 C46 O5 -176.2(8) . . . . ?
C48 N4 C46 O5 8.5(11) . . . . ?
C47 N4 C46 C39 7.9(12) . . . . ?
C48 N4 C46 C39 -167.4(6) . . . . ?
C38 C39 C46 O5 -1.4(12) . . . . ?
C40 C39 C46 O5 178.6(7) . . . . ?
C38 C39 C46 N4 174.2(7) . . . . ?
C40 C39 C46 N4 -5.8(11) . . . . ?
C46 N4 C47 O6 179.0(8) . . . . ?
C48 N4 C47 O6 -5.8(11) . . . . ?
C46 N4 C47 C41 -3.6(11) . . . . ?
C48 N4 C47 C41 171.6(6) . . . . ?
C42 C41 C47 O6 -2.7(12) . . . . ?
C40 C41 C47 O6 174.1(7) . . . . ?
C42 C41 C47 N4 -179.9(7) . . . . ?
C40 C41 C47 N4 -3.2(10) . . . . ?
C46 N4 C48 C49 -84.6(8) . . . . ?
C47 N4 C48 C49 99.9(8) . . . . ?
N4 C48 C49 C51 -68.4(9) . . . . ?
N4 C48 C49 C50 171.7(8) . . . . ?
