#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:13:21 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179472 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/69/4336953.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_4336953
loop_
_publ_author_name
'Derek Isrow'
'Nathan J. DeYonker'
'Anjaneyulu Koppaka'
'Perry J. Pellechia'
'Charles Edwin Webster'
'Burjor Captain'
_publ_section_title
;
 Metal-Ligand Synergistic Effects in the Complex Ni(η2-TEMPO)2:
 Synthesis, Structures, and Reactivity
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              13882
_journal_page_last               13893
_journal_paper_doi               10.1021/ic401296f
_journal_volume                  52
_journal_year                    2013
_chemical_formula_sum            'C58 H90 N4 Ni2 O4'
_chemical_formula_weight         1024.76
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.3960(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.7972(7)
_cell_length_b                   10.8726(6)
_cell_length_c                   18.9646(9)
_cell_measurement_reflns_used    6347
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.17
_cell_volume                     2788.8(2)
_computing_cell_refinement       'SAINT+  V7.46A (Bruker, 2007)'
_computing_data_collection       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_data_reduction        'SAINT+  V7.46A (Bruker, 2007)'
_computing_molecular_graphics    'XSHELL v4.02 (Bruker, 2000)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega 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  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            27734
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS 2007/4 Bruker)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1108
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.247
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         6729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0438P)²+2.0458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                5391
_reflns_number_total             6729
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic401296f_si_002_8.cif
_cod_data_source_block           compound_9
_cod_database_code               4336953
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
Ni1 Ni 0.736629(16) 0.29875(2) 0.780415(12) 0.01364(7) Uani 1 1 d .
O1 O 0.69546(9) 0.42599(12) 0.71418(7) 0.0161(3) Uani 1 1 d .
O2 O 0.62035(9) 0.21138(11) 0.78746(7) 0.0163(3) Uani 1 1 d .
N1 N 0.79715(11) 0.42706(14) 0.73979(8) 0.0149(3) Uani 1 1 d .
N2 N 0.63229(11) 0.09545(14) 0.82156(8) 0.0145(3) Uani 1 1 d .
H2 H 0.6981 0.0891 0.8404 0.017 Uiso 1 1 calc R
C1 C 0.82678(13) 0.20769(17) 0.84573(10) 0.0171(4) Uani 1 1 d .
C2 C 0.87973(14) 0.14501(18) 0.89080(10) 0.0187(4) Uani 1 1 d .
C3 C 0.94048(13) 0.07191(18) 0.94592(10) 0.0169(4) Uani 1 1 d .
C4 C 0.92838(13) -0.05632(18) 0.94827(10) 0.0179(4) Uani 1 1 d .
H4 H 0.8805 -0.0945 0.9138 0.022 Uiso 1 1 calc R
C5 C 1.01328(14) 0.12658(18) 0.99883(10) 0.0186(4) Uani 1 1 d .
H5 H 1.0225 0.2113 0.9984 0.022 Uiso 1 1 calc R
C11 C 0.83604(15) 0.4848(2) 0.61922(11) 0.0240(4) Uani 1 1 d .
H11A H 0.7669 0.5042 0.6072 0.036 Uiso 1 1 calc R
H11B H 0.8565 0.4493 0.5782 0.036 Uiso 1 1 calc R
H11C H 0.8732 0.5585 0.6332 0.036 Uiso 1 1 calc R
C12 C 0.81886(15) 0.26690(19) 0.65187(11) 0.0230(4) Uani 1 1 d .
H12A H 0.8276 0.2080 0.6903 0.035 Uiso 1 1 calc R
H12B H 0.8564 0.2418 0.6168 0.035 Uiso 1 1 calc R
H12C H 0.7501 0.2716 0.6297 0.035 Uiso 1 1 calc R
C13 C 0.81058(15) 0.66019(18) 0.74499(12) 0.0236(4) Uani 1 1 d .
H13A H 0.8577 0.6707 0.7144 0.035 Uiso 1 1 calc R
H13B H 0.8161 0.7274 0.7784 0.035 Uiso 1 1 calc R
H13C H 0.7450 0.6584 0.7162 0.035 Uiso 1 1 calc R
C14 C 0.77400(15) 0.5408(2) 0.84798(11) 0.0236(4) Uani 1 1 d .
H14A H 0.7052 0.5551 0.8287 0.035 Uiso 1 1 calc R
H14B H 0.7992 0.6054 0.8811 0.035 Uiso 1 1 calc R
H14C H 0.7817 0.4632 0.8726 0.035 Uiso 1 1 calc R
C15 C 0.85456(14) 0.39277(18) 0.68172(10) 0.0186(4) Uani 1 1 d .
C16 C 0.96387(14) 0.38337(19) 0.71827(11) 0.0224(4) Uani 1 1 d .
H16A H 0.9724 0.3127 0.7501 0.027 Uiso 1 1 calc R
H16B H 1.0028 0.3693 0.6817 0.027 Uiso 1 1 calc R
C17 C 1.00332(15) 0.4970(2) 0.76136(12) 0.0255(4) Uani 1 1 d .
H17A H 1.0718 0.4841 0.7845 0.031 Uiso 1 1 calc R
H17B H 1.0004 0.5673 0.7295 0.031 Uiso 1 1 calc R
C18 C 0.94153(14) 0.52188(19) 0.81786(11) 0.0224(4) Uani 1 1 d .
H18A H 0.9663 0.5954 0.8444 0.027 Uiso 1 1 calc R
H18B H 0.9496 0.4539 0.8516 0.027 Uiso 1 1 calc R
C19 C 0.83130(14) 0.53877(18) 0.78662(11) 0.0188(4) Uani 1 1 d .
C20 C 0.68893(15) -0.0013(2) 0.71995(11) 0.0232(4) Uani 1 1 d .
H20A H 0.6839 -0.0716 0.6888 0.035 Uiso 1 1 calc R
H20B H 0.7531 0.0000 0.7508 0.035 Uiso 1 1 calc R
H20C H 0.6797 0.0724 0.6916 0.035 Uiso 1 1 calc R
C21 C 0.50789(14) 0.00795(19) 0.71758(11) 0.0213(4) Uani 1 1 d .
H21A H 0.5031 -0.0420 0.6753 0.032 Uiso 1 1 calc R
H21B H 0.4988 0.0928 0.7038 0.032 Uiso 1 1 calc R
H21C H 0.4577 -0.0163 0.7434 0.032 Uiso 1 1 calc R
C22 C 0.63600(15) 0.18762(19) 0.93975(11) 0.0217(4) Uani 1 1 d .
H22A H 0.6289 0.2679 0.9183 0.033 Uiso 1 1 calc R
H22B H 0.7048 0.1663 0.9518 0.033 Uiso 1 1 calc R
H22C H 0.6087 0.1877 0.9826 0.033 Uiso 1 1 calc R
C23 C 0.47300(14) 0.13052(19) 0.86492(11) 0.0210(4) Uani 1 1 d .
H23A H 0.4458 0.1424 0.9073 0.031 Uiso 1 1 calc R
H23B H 0.4370 0.0668 0.8359 0.031 Uiso 1 1 calc R
H23C H 0.4679 0.2057 0.8379 0.031 Uiso 1 1 calc R
C24 C 0.60971(14) -0.00901(17) 0.76560(10) 0.0174(4) Uani 1 1 d .
C25 C 0.61933(15) -0.13145(18) 0.80658(11) 0.0215(4) Uani 1 1 d .
H25A H 0.5981 -0.1974 0.7726 0.026 Uiso 1 1 calc R
H25B H 0.6885 -0.1451 0.8276 0.026 Uiso 1 1 calc R
C26 C 0.55977(16) -0.13798(18) 0.86579(11) 0.0231(4) Uani 1 1 d .
H26A H 0.5694 -0.2172 0.8896 0.028 Uiso 1 1 calc R
H26B H 0.4899 -0.1284 0.8455 0.028 Uiso 1 1 calc R
C27 C 0.59415(15) -0.03552(18) 0.91966(11) 0.0208(4) Uani 1 1 d .
H27A H 0.6634 -0.0482 0.9407 0.025 Uiso 1 1 calc R
H27B H 0.5573 -0.0406 0.9581 0.025 Uiso 1 1 calc R
C28 C 0.58121(14) 0.09367(18) 0.88661(10) 0.0173(4) Uani 1 1 d .
C31 C 0.35106(17) 0.4820(2) 0.99257(12) 0.0306(5) Uani 1 1 d .
H31 H 0.4068 0.5281 1.0118 0.037 Uiso 1 1 calc R
C32 C 0.3600(2) 0.3614(2) 0.97747(14) 0.0403(6) Uani 1 1 d .
H32 H 0.4219 0.3244 0.9878 0.048 Uiso 1 1 calc R
C33 C 0.2793(2) 0.2934(2) 0.94726(15) 0.0410(6) Uani 1 1 d .
H33 H 0.2865 0.2109 0.9364 0.049 Uiso 1 1 calc R
C34 C 0.18591(19) 0.3481(3) 0.93272(13) 0.0374(6) Uani 1 1 d .
H34 H 0.1308 0.3018 0.9123 0.045 Uiso 1 1 calc R
C35 C 0.17557(19) 0.4667(3) 0.94804(13) 0.0392(6) Uani 1 1 d .
H35 H 0.1132 0.5027 0.9379 0.047 Uiso 1 1 calc R
C36 C 0.2575(2) 0.5370(2) 0.97913(13) 0.0386(6) Uani 1 1 d .
H36 H 0.2501 0.6192 0.9907 0.046 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'
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
C1 Ni1 N1 112.20(7) .
C1 Ni1 O1 155.76(7) .
N1 Ni1 O1 43.58(6) .
C1 Ni1 O2 98.67(7) .
N1 Ni1 O2 149.13(6) .
O1 Ni1 O2 105.56(5) .
N1 O1 Ni1 67.79(8) .
N2 O2 Ni1 117.19(10) .
O1 N1 C19 112.62(13) .
O1 N1 C15 112.20(14) .
C19 N1 C15 118.11(14) .
O1 N1 Ni1 68.63(8) .
C19 N1 Ni1 117.83(12) .
C15 N1 Ni1 116.98(12) .
O2 N2 C28 110.39(13) .
O2 N2 C24 110.65(13) .
C28 N2 C24 118.70(14) .
O2 N2 H2 105.3 .
C28 N2 H2 105.3 .
C24 N2 H2 105.3 .
C2 C1 Ni1 174.95(17) .
C1 C2 C3 178.1(2) .
C5 C3 C4 118.03(17) .
C5 C3 C2 121.06(18) .
C4 C3 C2 120.91(18) .
C5 C4 C3 120.94(18) 3_757
C5 C4 H4 119.5 3_757
C3 C4 H4 119.5 .
C4 C5 C3 121.03(18) 3_757
C4 C5 H5 119.5 3_757
C3 C5 H5 119.5 .
C15 C11 H11A 109.5 .
C15 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
C15 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
C15 C12 H12A 109.5 .
C15 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C15 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C19 C13 H13A 109.5 .
C19 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
C19 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
C19 C14 H14A 109.5 .
C19 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
C19 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
N1 C15 C12 108.17(15) .
N1 C15 C11 111.58(15) .
C12 C15 C11 107.84(17) .
N1 C15 C16 107.14(15) .
C12 C15 C16 108.94(16) .
C11 C15 C16 113.05(16) .
C17 C16 C15 113.83(16) .
C17 C16 H16A 108.8 .
C15 C16 H16A 108.8 .
C17 C16 H16B 108.8 .
C15 C16 H16B 108.8 .
H16A C16 H16B 107.7 .
C18 C17 C16 109.39(16) .
C18 C17 H17A 109.8 .
C16 C17 H17A 109.8 .
C18 C17 H17B 109.8 .
C16 C17 H17B 109.8 .
H17A C17 H17B 108.2 .
C17 C18 C19 113.67(17) .
C17 C18 H18A 108.8 .
C19 C18 H18A 108.8 .
C17 C18 H18B 108.8 .
C19 C18 H18B 108.8 .
H18A C18 H18B 107.7 .
N1 C19 C18 107.41(15) .
N1 C19 C14 107.94(15) .
C18 C19 C14 109.30(16) .
N1 C19 C13 112.40(16) .
C18 C19 C13 111.84(16) .
C14 C19 C13 107.86(16) .
C24 C20 H20A 109.5 .
C24 C20 H20B 109.5 .
H20A C20 H20B 109.5 .
C24 C20 H20C 109.5 .
H20A C20 H20C 109.5 .
H20B C20 H20C 109.5 .
C24 C21 H21A 109.5 .
C24 C21 H21B 109.5 .
H21A C21 H21B 109.5 .
C24 C21 H21C 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
C28 C22 H22A 109.5 .
C28 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
C28 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
C28 C23 H23A 109.5 .
C28 C23 H23B 109.5 .
H23A C23 H23B 109.5 .
C28 C23 H23C 109.5 .
H23A C23 H23C 109.5 .
H23B C23 H23C 109.5 .
C20 C24 C21 109.45(16) .
C20 C24 C25 109.59(16) .
C21 C24 C25 112.60(16) .
C20 C24 N2 106.26(15) .
C21 C24 N2 110.99(15) .
C25 C24 N2 107.74(15) .
C26 C25 C24 114.20(16) .
C26 C25 H25A 108.7 .
C24 C25 H25A 108.7 .
C26 C25 H25B 108.7 .
C24 C25 H25B 108.7 .
H25A C25 H25B 107.6 .
C25 C26 C27 108.64(16) .
C25 C26 H26A 110.0 .
C27 C26 H26A 110.0 .
C25 C26 H26B 110.0 .
C27 C26 H26B 110.0 .
H26A C26 H26B 108.3 .
C26 C27 C28 113.58(16) .
C26 C27 H27A 108.8 .
C28 C27 H27A 108.8 .
C26 C27 H27B 108.8 .
C28 C27 H27B 108.8 .
H27A C27 H27B 107.7 .
C23 C28 C22 109.49(16) .
C23 C28 C27 112.34(16) .
C22 C28 C27 109.91(16) .
C23 C28 N2 111.15(15) .
C22 C28 N2 106.01(14) .
C27 C28 N2 107.74(15) .
C32 C31 C36 119.7(2) .
C32 C31 H31 120.2 .
C36 C31 H31 120.2 .
C31 C32 C33 120.9(3) .
C31 C32 H32 119.6 .
C33 C32 H32 119.6 .
C32 C33 C34 119.8(3) .
C32 C33 H33 120.1 .
C34 C33 H33 120.1 .
C35 C34 C33 120.1(2) .
C35 C34 H34 119.9 .
C33 C34 H34 119.9 .
C34 C35 C36 120.6(2) .
C34 C35 H35 119.7 .
C36 C35 H35 119.7 .
C35 C36 C31 118.9(2) .
C35 C36 H36 120.5 .
C31 C36 H36 120.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 C1 1.8582(19) .
Ni1 N1 1.8685(16) .
Ni1 O1 1.8795(13) .
Ni1 O2 1.8918(13) .
O1 N1 1.3912(19) .
O2 N2 1.4114(19) .
N1 C19 1.523(2) .
N1 C15 1.524(2) .
N2 C28 1.537(2) .
N2 C24 1.544(2) .
N2 H2 0.9100 .
C1 C2 1.217(3) .
C2 C3 1.443(3) .
C3 C5 1.404(3) .
C3 C4 1.406(3) .
C4 C5 1.385(3) 3_757
C4 H4 0.9300 .
C5 C4 1.385(3) 3_757
C5 H5 0.9300 .
C11 C15 1.534(3) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C15 1.525(3) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 C19 1.536(3) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 C19 1.531(3) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 C16 1.534(3) .
C16 C17 1.522(3) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18 1.519(3) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 C19 1.530(3) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C20 C24 1.525(3) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 C24 1.527(3) .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C22 C28 1.526(3) .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C23 C28 1.522(3) .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C24 C25 1.534(3) .
C25 C26 1.518(3) .
C25 H25A 0.9700 .
C25 H25B 0.9700 .
C26 C27 1.522(3) .
C26 H26A 0.9700 .
C26 H26B 0.9700 .
C27 C28 1.534(3) .
C27 H27A 0.9700 .
C27 H27B 0.9700 .
C31 C32 1.353(3) .
C31 C36 1.400(3) .
C31 H31 0.9300 .
C32 C33 1.365(4) .
C32 H32 0.9300 .
C33 C34 1.396(4) .
C33 H33 0.9300 .
C34 C35 1.336(4) .
C34 H34 0.9300 .
C35 C36 1.396(3) .
C35 H35 0.9300 .
C36 H36 0.9300 .
