#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:58:00 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178542 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/48/4064864.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_4064864
loop_
_publ_author_name
'Weismann, Daniel'
'Saurenz, Dirk'
'Boese, Roland'
'Bläser, Dieter'
'Wolmershäuser, Gotthelf'
'Sun, Yu'
'Sitzmann, Helmut'
_publ_section_title
;
 Cyclopentadiene Alkylation and Nickel Complexes with Tri-, Tetra-, or
 Pentaisopropylcyclopentadienide or an Even Bulkier Lithium
 Alkylcyclopentadienide
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              6351
_journal_paper_doi               10.1021/om200372j
_journal_volume                  30
_journal_year                    2011
_chemical_formula_sum            'C50 H76 Ni2 O2'
_chemical_formula_weight         826.53
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 93.878(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.4040(8)
_cell_length_b                   14.2093(8)
_cell_length_c                   15.6601(12)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      1.9
_cell_volume                     2309.8(3)
_computing_cell_refinement       'Stoe IPDS V2.63'
_computing_data_collection       'Stoe IPDS V2.63'
_computing_data_reduction        'Stoe IPDS V2.63'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.725
_diffrn_measured_fraction_theta_max 0.725
_diffrn_measurement_device       'Stoe IPDS'
_diffrn_measurement_method       Phi-Oscillation
_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  0.1105
_diffrn_reflns_av_sigmaI/netI    0.0815
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13311
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.851
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent polyhedron'
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.914
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.046
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0689P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1179
_reflns_number_gt                2317
_reflns_number_total             3440
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om200372j_si_005.cif
_cod_data_source_block           2032
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0689P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0689P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4064864
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_calc_flag
_atom_site_refinement_flags
Ni1 Ni 0.20735(4) 0.63973(3) 0.26605(3) 0.03145(16) Uani 1 d .
O1 O 0.2607(4) 0.7500 0.1996(2) 0.0393(8) Uani 1 d S
O2 O 0.1687(4) 0.7500 0.3379(2) 0.0386(8) Uani 1 d S
C1 C 0.2357(4) 0.5072(2) 0.3385(3) 0.0341(9) Uani 1 d .
C2 C 0.3052(4) 0.5019(2) 0.2617(3) 0.0336(8) Uani 1 d .
C3 C 0.2123(3) 0.5081(2) 0.1888(2) 0.0356(8) Uani 1 d .
C4 C 0.0884(4) 0.5210(2) 0.2215(2) 0.0360(8) Uani 1 d .
C5 C 0.1032(4) 0.5204(3) 0.3118(3) 0.0371(9) Uani 1 d .
H5 H 0.0368 0.5275 0.3483 0.045 Uiso 1 calc R
C11 C 0.2832(4) 0.4890(3) 0.4311(2) 0.0418(9) Uani 1 d .
H11 H 0.3578 0.5294 0.4458 0.050 Uiso 1 calc R
C12 C 0.1805(4) 0.5083(3) 0.4933(3) 0.0494(10) Uani 1 d .
H12A H 0.1465 0.5705 0.4837 0.074 Uiso 1 calc R
H12B H 0.2177 0.5035 0.5509 0.074 Uiso 1 calc R
H12C H 0.1123 0.4631 0.4846 0.074 Uiso 1 calc R
C13 C 0.3243(5) 0.3856(3) 0.4420(3) 0.0631(13) Uani 1 d .
H13A H 0.2570 0.3456 0.4179 0.095 Uiso 1 calc R
H13B H 0.3402 0.3717 0.5018 0.095 Uiso 1 calc R
H13C H 0.4015 0.3751 0.4131 0.095 Uiso 1 calc R
C20 C -0.0821(7) 0.7500 0.4014(5) 0.0624(19) Uani 1 d S
H20A H -0.0671 0.7825 0.3492 0.094 Uiso 0.50 calc PR
H20B H -0.1493 0.7812 0.4295 0.094 Uiso 0.50 calc PR
H20C H -0.1074 0.6863 0.3886 0.094 Uiso 0.50 calc PR
C21 C 0.4498(5) 0.4846(3) 0.2542(3) 0.0459(12) Uani 1 d .
H21 H 0.4731 0.5192 0.2033 0.055 Uiso 1 calc R
C22 C 0.5391(4) 0.5204(3) 0.3280(3) 0.0579(11) Uani 1 d .
H22A H 0.5181 0.5847 0.3401 0.087 Uiso 1 calc R
H22B H 0.6267 0.5168 0.3126 0.087 Uiso 1 calc R
H22C H 0.5287 0.4825 0.3778 0.087 Uiso 1 calc R
C23 C 0.4756(5) 0.3798(3) 0.2362(4) 0.0672(14) Uani 1 d .
H23A H 0.4521 0.3425 0.2839 0.101 Uiso 1 calc R
H23B H 0.5654 0.3709 0.2279 0.101 Uiso 1 calc R
H23C H 0.4252 0.3606 0.1855 0.101 Uiso 1 calc R
C24 C 0.1600(6) 0.7500 0.4251(3) 0.0399(13) Uani 1 d S
C25 C 0.0389(6) 0.7500 0.4588(4) 0.0440(13) Uani 1 d S
C26 C 0.0345(8) 0.7500 0.5480(5) 0.0608(19) Uani 1 d S
H26 H -0.0448 0.7500 0.5721 0.073 Uiso 1 calc SR
C27 C 0.1464(9) 0.7500 0.6005(4) 0.075(2) Uani 1 d S
H27 H 0.1421 0.7500 0.6596 0.090 Uiso 1 calc SR
C28 C 0.2614(8) 0.7500 0.5666(4) 0.0666(19) Uani 1 d S
H28 H 0.3359 0.7500 0.6030 0.080 Uiso 1 calc SR
C29 C 0.2726(6) 0.7500 0.4781(4) 0.0504(15) Uani 1 d S
C30 C 0.4007(6) 0.7500 0.4408(5) 0.0652(18) Uani 1 d S
H30A H 0.4017 0.7028 0.3970 0.098 Uiso 0.50 calc PR
H30B H 0.4667 0.7366 0.4850 0.098 Uiso 0.50 calc PR
H30C H 0.4161 0.8106 0.4165 0.098 Uiso 0.50 calc PR
C31 C 0.2258(5) 0.4923(3) 0.0942(3) 0.0477(11) Uani 1 d .
H31 H 0.1628 0.5336 0.0636 0.057 Uiso 1 calc R
C32 C 0.3550(5) 0.5112(3) 0.0569(3) 0.0576(12) Uani 1 d .
H32A H 0.3880 0.5708 0.0772 0.086 Uiso 1 calc R
H32B H 0.3435 0.5124 -0.0045 0.086 Uiso 1 calc R
H32C H 0.4147 0.4623 0.0744 0.086 Uiso 1 calc R
C33 C 0.1855(5) 0.3906(3) 0.0711(3) 0.0672(13) Uani 1 d .
H33A H 0.1970 0.3793 0.0117 0.101 Uiso 1 calc R
H33B H 0.0965 0.3817 0.0819 0.101 Uiso 1 calc R
H33C H 0.2377 0.3474 0.1055 0.101 Uiso 1 calc R
C40 C 0.1040(7) 0.7500 0.0450(5) 0.070(2) Uani 1 d S
H40A H 0.0755 0.7012 0.0816 0.105 Uiso 0.50 calc PR
H40B H 0.0698 0.7390 -0.0126 0.105 Uiso 0.50 calc PR
H40C H 0.0744 0.8099 0.0642 0.105 Uiso 0.50 calc PR
C41 C -0.0423(4) 0.5226(3) 0.1725(3) 0.0471(11) Uani 1 d .
H41 H -0.0281 0.5274 0.1115 0.057 Uiso 1 calc R
C42 C -0.1262(4) 0.6050(4) 0.1955(3) 0.0642(12) Uani 1 d .
H42A H -0.1494 0.5983 0.2535 0.096 Uiso 1 calc R
H42B H -0.2029 0.6060 0.1578 0.096 Uiso 1 calc R
H42C H -0.0796 0.6627 0.1898 0.096 Uiso 1 calc R
C43 C -0.1143(4) 0.4295(3) 0.1866(4) 0.0758(15) Uani 1 d .
H43A H -0.0581 0.3774 0.1774 0.114 Uiso 1 calc R
H43B H -0.1887 0.4258 0.1470 0.114 Uiso 1 calc R
H43C H -0.1408 0.4274 0.2441 0.114 Uiso 1 calc R
C44 C 0.3202(5) 0.7500 0.1242(3) 0.0396(12) Uani 1 d S
C45 C 0.4559(6) 0.7500 0.1272(4) 0.0510(15) Uani 1 d S
C46 C 0.5146(8) 0.7500 0.0505(5) 0.066(2) Uani 1 d S
H46 H 0.6041 0.7500 0.0516 0.079 Uiso 1 calc SR
C47 C 0.4459(9) 0.7500 -0.0259(5) 0.069(2) Uani 1 d S
H47 H 0.4879 0.7500 -0.0765 0.083 Uiso 1 calc SR
C48 C 0.3134(9) 0.7500 -0.0282(4) 0.069(2) Uani 1 d S
H48 H 0.2664 0.7500 -0.0809 0.083 Uiso 1 calc SR
C49 C 0.2472(6) 0.7500 0.0476(4) 0.0465(14) Uani 1 d S
C50 C 0.5343(6) 0.7500 0.2110(5) 0.0678(19) Uani 1 d S
H50A H 0.6114 0.7861 0.2057 0.102 Uiso 0.50 calc PR
H50B H 0.5568 0.6865 0.2267 0.102 Uiso 0.50 calc PR
H50C H 0.4850 0.7774 0.2543 0.102 Uiso 0.50 calc PR
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'
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
_geom_angle_site_symmetry_3
O1 Ni1 O2 75.42(11) . .
O1 Ni1 C5 163.67(16) . .
O2 Ni1 C5 107.82(14) . .
O1 Ni1 C4 128.10(15) . .
O2 Ni1 C4 131.30(14) . .
C5 Ni1 C4 38.01(15) . .
O1 Ni1 C1 155.79(14) . .
O2 Ni1 C1 114.04(13) . .
C5 Ni1 C1 38.06(14) . .
C4 Ni1 C1 63.74(14) . .
O1 Ni1 C2 122.56(13) . .
O2 Ni1 C2 145.90(14) . .
C5 Ni1 C2 63.74(15) . .
C4 Ni1 C2 63.72(14) . .
C1 Ni1 C2 38.23(13) . .
O1 Ni1 C3 111.14(13) . .
O2 Ni1 C3 169.14(14) . .
C5 Ni1 C3 63.40(15) . .
C4 Ni1 C3 37.84(13) . .
C1 Ni1 C3 63.64(15) . .
C2 Ni1 C3 38.05(14) . .
C44 O1 Ni1 127.74(8) . .
C44 O1 Ni1 127.74(8) . 4_575
Ni1 O1 Ni1 104.52(16) . 4_575
C24 O2 Ni1 126.30(11) . 4_575
C24 O2 Ni1 126.30(11) . .
Ni1 O2 Ni1 104.20(15) 4_575 .
C2 C1 C5 107.0(4) . .
C2 C1 C11 129.4(3) . .
C5 C1 C11 123.1(4) . .
C2 C1 Ni1 71.0(2) . .
C5 C1 Ni1 69.2(2) . .
C11 C1 Ni1 131.1(3) . .
C1 C2 C3 107.9(3) . .
C1 C2 C21 128.2(4) . .
C3 C2 C21 123.7(4) . .
C1 C2 Ni1 70.8(2) . .
C3 C2 Ni1 71.71(19) . .
C21 C2 Ni1 126.8(3) . .
C4 C3 C2 107.2(3) . .
C4 C3 C31 120.9(3) . .
C2 C3 C31 131.4(3) . .
C4 C3 Ni1 69.15(18) . .
C2 C3 Ni1 70.24(19) . .
C31 C3 Ni1 131.5(3) . .
C5 C4 C3 108.5(3) . .
C5 C4 C41 122.7(4) . .
C3 C4 C41 128.4(3) . .
C5 C4 Ni1 70.3(2) . .
C3 C4 Ni1 73.01(19) . .
C41 C4 Ni1 128.4(3) . .
C4 C5 C1 109.4(4) . .
C4 C5 Ni1 71.7(2) . .
C1 C5 Ni1 72.7(2) . .
C1 C11 C12 112.5(3) . .
C1 C11 C13 109.7(3) . .
C12 C11 C13 107.7(3) . .
C2 C21 C22 116.1(4) . .
C2 C21 C23 110.5(4) . .
C22 C21 C23 111.0(4) . .
O2 C24 C29 118.9(5) . .
O2 C24 C25 119.7(5) . .
C29 C24 C25 121.3(5) . .
C24 C25 C26 117.9(6) . .
C24 C25 C20 121.1(5) . .
C26 C25 C20 121.1(6) . .
C27 C26 C25 120.8(6) . .
C28 C27 C26 120.2(7) . .
C27 C28 C29 121.9(7) . .
C24 C29 C28 117.9(6) . .
C24 C29 C30 120.4(6) . .
C28 C29 C30 121.6(6) . .
C32 C31 C3 119.4(4) . .
C32 C31 C33 108.0(4) . .
C3 C31 C33 109.1(4) . .
C4 C41 C42 113.8(4) . .
C4 C41 C43 110.0(4) . .
C42 C41 C43 109.5(4) . .
C49 C44 O1 119.8(5) . .
C49 C44 C45 121.4(5) . .
O1 C44 C45 118.8(5) . .
C46 C45 C44 118.1(7) . .
C46 C45 C50 121.0(6) . .
C44 C45 C50 120.9(5) . .
C47 C46 C45 122.0(7) . .
C46 C47 C48 119.5(7) . .
C47 C48 C49 121.5(7) . .
C44 C49 C48 117.5(6) . .
C44 C49 C40 121.0(6) . .
C48 C49 C40 121.4(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O1 1.981(2) .
Ni1 O2 1.986(2) .
Ni1 C5 2.161(4) .
Ni1 C4 2.179(3) .
Ni1 C1 2.207(4) .
Ni1 C2 2.210(3) .
Ni1 C3 2.230(3) .
O1 C44 1.368(6) .
O1 Ni1 1.981(2) 4_575
O2 C24 1.376(6) .
O2 Ni1 1.986(2) 4_575
C1 C2 1.447(5) .
C1 C5 1.425(6) .
C1 C11 1.524(5) .
C2 C3 1.448(5) .
C2 C21 1.537(6) .
C3 C4 1.430(5) .
C3 C31 1.515(6) .
C4 C5 1.413(6) .
C4 C41 1.515(6) .
C11 C12 1.519(6) .
C11 C13 1.536(5) .
C20 C25 1.497(9) .
C21 C22 1.520(6) .
C21 C23 1.544(6) .
C24 C29 1.389(8) .
C24 C25 1.398(8) .
C25 C26 1.401(9) .
C26 C27 1.379(11) .
C27 C28 1.342(11) .
C28 C29 1.398(9) .
C29 C30 1.491(9) .
C31 C32 1.525(6) .
C31 C33 1.540(6) .
C40 C49 1.488(9) .
C41 C42 1.518(6) .
C41 C43 1.543(6) .
C44 C49 1.376(8) .
C44 C45 1.410(8) .
C45 C46 1.383(9) .
C45 C50 1.498(10) .
C46 C47 1.351(12) .
C47 C48 1.377(11) .
C48 C49 1.411(9) .
