#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/46/2004604.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2004604
loop_
_publ_author_name
'Ficker, R.'
'Hiller, W.'
'Ossig, A.'
'Schurig, V.'
_publ_section_title
;
 Nickel(II) Bis(d-campholyl-l-campholylmethanate)
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              543
_journal_page_last               545
_journal_paper_doi               10.1107/S0108270195010663
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac          '[Ni1 (C21 H35 O2)2]'
_chemical_formula_moiety         'C42 H70 Ni O4'
_chemical_formula_sum            'C42 H70 Ni O4'
_chemical_formula_weight         697.69
_chemical_name_common            Nickel(II)-bis-[(d,l)-dicampholylmethanat]
_chemical_name_systematic
;
Nickel(II)-bis[1-((+)-(1'R,3'S)-1',2',2',3'-tetramethyl-cyclopent-1'yl)-
3-((-)-(1'S,3'R)-1',2',2',3'-tetramethyl-cyclopent-1'yl)-propan-1,3-
dionate]
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           'from SHELXL-93'
_cell_angle_alpha                114.805(9)
_cell_angle_beta                 98.699(9)
_cell_angle_gamma                100.923(9)
_cell_formula_units_Z            1
_cell_length_a                   7.3319(8)
_cell_length_b                   12.3885(9)
_cell_length_c                   12.8313(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      38
_cell_measurement_theta_min      16
_cell_volume                     1003.38(19)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CADHKL4 in CADSHEL (Kopf & Ruebcke, 1993)'
_computing_molecular_graphics    'SHELXTL/PC (Siemens, 1990)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  '0.016 (F)'
_diffrn_reflns_av_sigmaI/netI    0.0140
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3715
_diffrn_reflns_theta_max         65
_diffrn_reflns_theta_min         4
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.948
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.201
_exptl_absorpt_correction_type   'empirical (DIFABS; Walker & Stuart, 1983)'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_description       needles
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         .395
_refine_diff_density_min         -.274
_refine_ls_extinction_coef       0.0120(10)
_refine_ls_extinction_method     SHELXL93
_refine_ls_goodness_of_fit_all   1.119
_refine_ls_goodness_of_fit_obs   1.126
_refine_ls_hydrogen_treatment
;
H(2) refined freely, other H atoms refined as riding model
(SHELXL93; Sheldrick, 1993)
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         1432
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_restrained_S_obs      1.126
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_obs          0.0446
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.1130P)^2^ + 1.6245P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.1204
_refine_ls_wR_factor_obs         0.1163
_reflns_number_observed          1432
_reflns_number_total             3419
_reflns_observed_criterion       >4sigma(F)
_cod_data_source_file            fg1065.cif
_cod_data_source_block           ossig
_cod_original_cell_volume        1003.37(2)
_cod_original_formula_sum        'C42 H70 Ni1 O4'
_cod_database_code               2004604
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
Ni 1 0.5000 0.5000 0.5000 0.0373(5) Uani d S Ni
O1 1 0.3951(3) 0.6259(2) 0.5068(2) 0.0419(8) Uani d . O
O2 1 0.5421(3) 0.5471(2) 0.6589(2) 0.0402(7) Uani d . O
C1 1 0.3427(5) 0.6974(3) 0.5951(4) 0.038(1) Uani d . C
C2 1 0.3809(6) 0.7011(4) 0.7051(4) 0.043(1) Uani d . C
H2 1 0.349(4) 0.755(3) 0.761(3) 0.02(1) Uiso d . H
C3 1 0.4874(5) 0.6316(4) 0.7353(3) 0.039(1) Uani d . C
C4 1 0.2441(5) 0.7863(3) 0.5709(3) 0.040(1) Uani d . C
C5 1 0.1012(5) 0.7275(3) 0.4461(3) 0.044(1) Uani d . C
C6 1 -0.0192(5) 0.8208(4) 0.4629(3) 0.049(1) Uani d . C
H6 1 0.0603(5) 0.8939(4) 0.4628(3) 0.059 Uiso calc R H
C7 1 -0.0451(7) 0.8595(5) 0.5870(4) 0.078(2) Uani d . C
H7A 1 -0.1698(7) 0.8130(5) 0.5839(4) 0.093 Uiso calc R H
H7B 1 -0.0366(7) 0.9471(5) 0.6258(4) 0.093 Uiso calc R H
C8 1 0.1152(7) 0.8328(5) 0.6549(4) 0.073(2) Uani d . C
H8A 1 0.0616(7) 0.7702(5) 0.6771(4) 0.087 Uiso calc R H
H8B 1 0.1891(7) 0.9075(5) 0.7266(4) 0.087 Uiso calc R H
C13 1 0.5498(5) 0.6567(3) 0.8646(3) 0.039(1) Uani d . C
C14 1 0.7248(5) 0.7765(3) 0.9368(3) 0.045(1) Uani d . C
C15 1 0.8144(6) 0.7581(4) 1.0417(3) 0.054(1) Uani d . C
H15 1 0.7315(6) 0.7752(4) 1.0964(3) 0.065 Uiso calc R H
C16 1 0.7977(7) 0.6206(4) 0.9889(4) 0.078(2) Uani d . C
H16A 1 0.7722(7) 0.5901(4) 1.0451(4) 0.093 Uiso calc R H
H16B 1 0.9164(7) 0.6054(4) 0.9696(4) 0.093 Uiso calc R H
C17 1 0.6327(7) 0.5557(4) 0.8772(4) 0.064(1) Uani d . C
H17A 1 0.5345(7) 0.4960(4) 0.8837(4) 0.077 Uiso calc R H
H17B 1 0.6783(7) 0.5123(4) 0.8083(4) 0.077 Uiso calc R H
C12 1 0.4111(6) 0.8963(4) 0.5922(5) 0.079(2) Uani d . C
H12A 1 0.3599(6) 0.956(1) 0.578(3) 0.118 Uiso calc R H
H12B 1 0.490(3) 0.8668(6) 0.539(2) 0.118 Uiso calc R H
H12C 1 0.487(3) 0.934(2) 0.6729(8) 0.118 Uiso calc R H
C10 1 0.1978(8) 0.7147(5) 0.3452(4) 0.084(2) Uani d . C
H10A 1 0.268(4) 0.7953(6) 0.359(2) 0.125 Uiso calc R H
H10B 1 0.1014(9) 0.676(3) 0.2709(5) 0.125 Uiso calc R H
H10C 1 0.285(4) 0.665(3) 0.342(2) 0.125 Uiso calc R H
C9 1 -0.0245(6) 0.6006(4) 0.4171(4) 0.077(2) Uani d . C
H9A 1 0.053(1) 0.5444(8) 0.407(3) 0.116 Uiso calc R H
H9B 1 -.122(3) 0.570(1) 0.345(2) 0.116 Uiso calc R H
H9C 1 -.082(3) 0.6075(6) 0.481(1) 0.116 Uiso calc R H
C11 1 -0.2090(6) 0.7755(5) 0.3683(4) 0.076(1) Uani d . C
H11A 1 -.264(2) 0.8427(8) 0.383(2) 0.114 Uiso calc R H
H11B 1 -.295(2) 0.710(2) 0.372(2) 0.114 Uiso calc R H
H11C 1 -0.1850(9) 0.746(3) 0.2910(5) 0.114 Uiso calc R H
C18 1 0.3771(6) 0.6646(5) 0.9194(4) 0.068(1) Uani d . C
H18A 1 0.415(1) 0.675(3) 0.999(1) 0.103 Uiso calc R H
H18B 1 0.274(2) 0.590(1) 0.872(2) 0.103 Uiso calc R H
H18C 1 0.335(3) 0.734(2) 0.922(2) 0.103 Uiso calc R H
C20 1 0.6677(7) 0.8982(4) 0.9813(4) 0.080(2) Uani d . C
H20A 1 0.612(4) 0.908(2) 0.9145(4) 0.119 Uiso calc R H
H20B 1 0.780(1) 0.9665(5) 1.030(2) 0.119 Uiso calc R H
H20C 1 0.576(4) 0.896(1) 1.027(3) 0.119 Uiso calc R H
C19 1 0.8642(6) 0.7803(4) 0.8607(4) 0.068(1) Uani d . C
H19A 1 0.897(3) 0.703(1) 0.830(2) 0.101 Uiso calc R H
H19B 1 0.979(2) 0.847(2) 0.9085(7) 0.101 Uiso calc R H
H19C 1 0.805(2) 0.793(3) 0.796(2) 0.101 Uiso calc R H
C21 1 1.0186(6) 0.8405(5) 1.1136(4) 0.081(2) Uani d . C
H21A 1 1.052(2) 0.832(2) 1.184(1) 0.122 Uiso calc R H
H21B 1 1.024(1) 0.9254(6) 1.135(2) 0.122 Uiso calc R H
H21C 1 1.1075(8) 0.816(2) 1.067(1) 0.122 Uiso calc R H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 .5091 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 Ni O2 . 2_666 180.0 no
O2 Ni O1 . 2_666 85.30(10) no
O2 Ni O1 2_666 2_666 94.80(10) no
O2 Ni O1 . . 94.80(10) yes
O2 Ni O1 2_666 . 85.30(10) no
O1 Ni O1 2_666 . 180.0 no
C1 O1 Ni . . 125.9(2) yes
C3 O2 Ni . . 127.2(2) yes
O1 C1 C2 . . 123.8(4) yes
O1 C1 C4 . . 114.1(3) yes
C2 C1 C4 . . 122.1(4) yes
C1 C2 C3 . . 124.4(4) yes
O2 C3 C2 . . 122.7(4) yes
O2 C3 C13 . . 116.6(3) yes
C2 C3 C13 . . 120.6(4) yes
C1 C4 C8 . . 112.6(3) no
C1 C4 C12 . . 104.7(3) no
C8 C4 C12 . . 109.9(3) no
C1 C4 C5 . . 114.6(3) no
C8 C4 C5 . . 102.4(3) no
C12 C4 C5 . . 112.9(3) no
C9 C5 C10 . . 108.9(4) no
C9 C5 C6 . . 110.9(3) no
C10 C5 C6 . . 110.3(3) no
C9 C5 C4 . . 110.2(3) no
C10 C5 C4 . . 114.2(3) no
C6 C5 C4 . . 102.2(3) no
C7 C6 C11 . . 113.2(3) no
C7 C6 C5 . . 104.6(3) no
C11 C6 C5 . . 116.3(3) no
C6 C7 C8 . . 107.0(3) no
C7 C8 C4 . . 106.7(3) no
C3 C13 C18 . . 109.7(3) no
C3 C13 C17 . . 112.8(3) no
C18 C13 C17 . . 108.7(3) no
C3 C13 C14 . . 110.5(3) no
C18 C13 C14 . . 112.6(3) no
C17 C13 C14 . . 102.5(3) no
C19 C14 C15 . . 111.2(3) no
C19 C14 C20 . . 108.6(3) no
C15 C14 C20 . . 110.5(3) no
C19 C14 C13 . . 109.9(3) no
C15 C14 C13 . . 102.5(3) no
C20 C14 C13 . . 114.1(3) no
C16 C15 C14 . . 104.8(3) no
C16 C15 C21 . . 113.3(4) no
C14 C15 C21 . . 116.5(3) no
C15 C16 C17 . . 107.1(3) no
C16 C17 C13 . . 107.2(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni O2 . 1.826(2) yes
Ni O2 2_666 1.826(2) no
Ni O1 2_666 1.842(2) no
Ni O1 . 1.842(2) yes
O1 C1 . 1.279(4) yes
O2 C3 . 1.279(4) yes
C1 C2 . 1.375(5) yes
C1 C4 . 1.535(5) no
C2 C3 . 1.395(6) yes
C3 C13 . 1.531(5) no
C4 C8 . 1.543(5) no
C4 C12 . 1.544(5) no
C4 C5 . 1.555(5) no
C5 C9 . 1.521(6) no
C5 C10 . 1.534(6) no
C5 C6 . 1.549(5) no
C6 C7 . 1.511(6) no
C6 C11 . 1.532(6) no
C7 C8 . 1.526(6) no
C13 C18 . 1.537(5) no
C13 C17 . 1.546(5) no
C13 C14 . 1.572(5) no
C14 C19 . 1.524(5) no
C14 C15 . 1.530(5) no
C14 C20 . 1.536(5) no
C15 C16 . 1.518(6) no
C15 C21 . 1.532(6) no
C16 C17 . 1.518(6) no
