#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:28:45 +0100 (vie 25 de mar de 2016) $
#$Revision: 179792 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/88/7008885.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_7008885
loop_
_publ_author_name
'Senge, Mathias O.'
'Renner, Mark W.'
'Kalisch, Werner W.'
'Fajer, Jack'
_publ_section_title
;
 Molecular structure of
 (5,10,15,20-tetrabutyl-2,3,7,8,12,13,17,18-octaethylporphyrinato)nickel(II)---correlation
 of nonplanarity with frontier orbital shifts †
;
_journal_issue                   3
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              381
_journal_paper_doi               10.1039/a905927j
_journal_year                    2000
_chemical_formula_moiety         'C52 H76 N4 Ni'
_chemical_formula_sum            'C52 H76 N4 Ni'
_chemical_formula_weight         815.88
_chemical_name_common            Ni(II)TnBuOEP
_chemical_name_systematic
; 
 (5,10,15,20-Tetra(n-butyl)-2,3,7,8,12,13,17,18-
 octaethylporphyrinato)nickel(II) 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 119.62(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.581(11)
_cell_length_b                   7.566(2)
_cell_length_c                   25.967(12)
_cell_measurement_reflns_used    32
_cell_measurement_temperature    126(2)
_cell_measurement_theta_max      33
_cell_measurement_theta_min      24
_cell_volume                     4540(3)
_computing_cell_refinement       'Siemens, P3'
_computing_data_collection       'Siemens, P3'
_computing_data_reduction        'XDISK, Shelxtl-Plus, Siemens, 1994'
_computing_molecular_graphics    'XP, Shelxtl-Plus, Siemens, 1994'
_computing_publication_material  'XCIF, Shelxtl-Plus, Siemens, 1994'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      126(2)
_diffrn_detector_area_resol_mean n/a
_diffrn_measured_fraction_theta_full 0.457
_diffrn_measured_fraction_theta_max 0.457
_diffrn_measurement_device_type  'Syntex P21'
_diffrn_measurement_method       2theta-theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1080
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3431
_diffrn_reflns_theta_full        57.08
_diffrn_reflns_theta_max         57.08
_diffrn_reflns_theta_min         3.83
_diffrn_standards_decay_%        stable
_diffrn_standards_interval_count 198
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.897
_exptl_absorpt_correction_T_max  0.6153
_exptl_absorpt_correction_T_min  0.6153
_exptl_absorpt_correction_type   'empirical, XABS2'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.60
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       n/d
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0780P)²+15.2512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1469
_reflns_number_gt                2780
_reflns_number_total             3058
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            a905927j.txt
_cod_data_source_block           ms404
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/d' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0780P)^2^+15.2512P] 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^)+(0.0780P)^2^+15.2512P] 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      C2/c
_cod_database_code               7008885
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni 0.0000 0.59772(9) 0.2500 0.0106(2) Uani 1 d S . .
N21 N 0.03085(10) 0.5961(3) 0.33232(10) 0.0131(6) Uani 1 d . . .
N22 N 0.07480(10) 0.5940(3) 0.26022(11) 0.0143(6) Uani 1 d . . .
C1 C 0.00561(12) 0.6667(4) 0.36266(13) 0.0127(7) Uani 1 d . . .
C2 C 0.04358(13) 0.6395(4) 0.42560(13) 0.0148(7) Uani 1 d . . .
C3 C 0.08980(12) 0.5421(4) 0.43200(13) 0.0134(7) Uani 1 d . . .
C4 C 0.08224(12) 0.5178(4) 0.37289(13) 0.0127(7) Uani 1 d . . .
C5 C 0.12267(12) 0.4506(4) 0.35801(13) 0.0133(7) Uani 1 d . . .
C6 C 0.12195(12) 0.5107(4) 0.30638(13) 0.0120(7) Uani 1 d . . .
C7 C 0.17013(13) 0.5192(4) 0.29490(13) 0.0142(7) Uani 1 d . . .
C8 C 0.15218(13) 0.6175(4) 0.24448(13) 0.0146(7) Uani 1 d . . .
C9 C 0.09157(12) 0.6586(4) 0.22209(13) 0.0132(7) Uani 1 d . . .
C10 C 0.05244(13) 0.7267(4) 0.16581(13) 0.0150(7) Uani 1 d . . .
C21 C 0.03582(14) 0.6946(5) 0.47716(14) 0.0218(7) Uani 1 d . . .
H21A H 0.0534 0.6038 0.5086 0.026 Uiso 1 calc R . .
H21B H -0.0060 0.7000 0.4639 0.026 Uiso 1 calc R . .
C22 C 0.06314(15) 0.8735(5) 0.50294(16) 0.0350(10) Uani 1 d . . .
H22A H 0.0569 0.9024 0.5362 0.053 Uiso 1 calc R . .
H22B H 0.0453 0.9646 0.4723 0.053 Uiso 1 calc R . .
H22C H 0.1048 0.8685 0.5169 0.053 Uiso 1 calc R . .
C31 C 0.13995(13) 0.4873(4) 0.49090(13) 0.0195(7) Uani 1 d . . .
H31A H 0.1468 0.5804 0.5205 0.023 Uiso 1 calc R . .
H31B H 0.1751 0.4786 0.4871 0.023 Uiso 1 calc R . .
C32 C 0.13080(16) 0.3116(5) 0.51381(15) 0.0283(8) Uani 1 d . . .
H32A H 0.1649 0.2841 0.5520 0.042 Uiso 1 calc R . .
H32B H 0.1249 0.2178 0.4853 0.042 Uiso 1 calc R . .
H32C H 0.0967 0.3198 0.5188 0.042 Uiso 1 calc R . .
C51 C 0.16340(13) 0.3039(4) 0.39416(13) 0.0170(7) Uani 1 d . . .
H51A H 0.1593 0.2800 0.4294 0.020 Uiso 1 calc R . .
H51B H 0.2039 0.3405 0.4080 0.020 Uiso 1 calc R . .
C52 C 0.14973(14) 0.1351(4) 0.35650(14) 0.0213(7) Uani 1 d . . .
H52A H 0.1090 0.1016 0.3424 0.026 Uiso 1 calc R . .
H52B H 0.1534 0.1617 0.3212 0.026 Uiso 1 calc R . .
C53 C 0.18837(15) -0.0227(5) 0.38876(15) 0.0266(8) Uani 1 d D . .
H53A H 0.1785 -0.1211 0.3603 0.032 Uiso 1 calc R . .
H53B H 0.2291 0.0105 0.4027 0.032 Uiso 1 calc R . .
C54 C 0.18338(19) -0.0863(5) 0.44032(18) 0.0396(10) Uani 1 d D . .
H54A H 0.2092 -0.1874 0.4585 0.059 Uiso 1 calc R . .
H54B H 0.1434 -0.1224 0.4269 0.059 Uiso 1 calc R . .
H54C H 0.1942 0.0090 0.4695 0.059 Uiso 1 calc R . .
C71 C 0.23105(13) 0.4505(4) 0.33219(14) 0.0193(7) Uani 1 d . . .
H71A H 0.2485 0.4327 0.3065 0.023 Uiso 1 calc R . .
H71B H 0.2296 0.3341 0.3488 0.023 Uiso 1 calc R . .
C72 C 0.26950(14) 0.5741(5) 0.38272(16) 0.0300(9) Uani 1 d . . .
H72A H 0.3083 0.5231 0.4053 0.045 Uiso 1 calc R . .
H72B H 0.2530 0.5900 0.4089 0.045 Uiso 1 calc R . .
H72C H 0.2719 0.6889 0.3666 0.045 Uiso 1 calc R . .
C81 C 0.18805(14) 0.6498(5) 0.21528(15) 0.0244(8) Uani 1 d . . .
H81A H 0.2295 0.6534 0.2460 0.029 Uiso 1 calc R . .
H81B H 0.1777 0.7663 0.1953 0.029 Uiso 1 calc R . .
C82 C 0.17914(18) 0.5079(6) 0.17013(17) 0.0378(10) Uani 1 d . . .
H82A H 0.2032 0.5343 0.1522 0.057 Uiso 1 calc R . .
H82B H 0.1383 0.5053 0.1392 0.057 Uiso 1 calc R . .
H82C H 0.1901 0.3926 0.1898 0.057 Uiso 1 calc R . .
C101 C 0.07274(14) 0.8565(5) 0.13544(14) 0.0232(8) Uani 1 d . . .
H10A H 0.0391 0.8945 0.0976 0.028 Uiso 1 calc R . .
H10B H 0.1004 0.7963 0.1262 0.028 Uiso 1 calc R . .
C102 C 0.10211(14) 1.0207(5) 0.17362(15) 0.0253(8) Uani 1 d . . .
H10C H 0.1294 0.9810 0.2144 0.030 Uiso 1 calc R . .
H10D H 0.1251 1.0790 0.1580 0.030 Uiso 1 calc R . .
C103 C 0.0622(2) 1.1549(8) 0.1765(3) 0.0751(18) Uani 1 d D . .
H10E H 0.0870 1.2489 0.2037 0.090 Uiso 1 calc R A 1
H10F H 0.0408 1.2091 0.1367 0.090 Uiso 1 calc R A 1
C104 C 0.0193(3) 1.1122(9) 0.1940(3) 0.043(2) Uani 0.646(11) d PD B 1
H10G H -0.0017 1.2195 0.1930 0.065 Uiso 0.646(11) calc PR B 1
H10H H 0.0388 1.0636 0.2343 0.065 Uiso 0.646(11) calc PR B 1
H10I H -0.0079 1.0247 0.1666 0.065 Uiso 0.646(11) calc PR B 1
C10D C 0.0078(5) 1.179(2) 0.1382(7) 0.068(6) Uani 0.354(11) d P B 2
H10J H -0.0075 1.2758 0.1516 0.103 Uiso 0.354(11) calc PR B 2
H10K H -0.0138 1.0708 0.1344 0.103 Uiso 0.354(11) calc PR B 2
H10L H 0.0038 1.2098 0.0997 0.103 Uiso 0.354(11) calc PR B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N22 Ni N22 178.29(16) . 2 ?
N22 Ni N21 89.82(11) . 2 ?
N22 Ni N21 90.17(11) 2 2 ?
N22 Ni N21 90.17(11) . . ?
N22 Ni N21 89.82(11) 2 . ?
N21 Ni N21 179.26(16) 2 . ?
C1 N21 C4 108.0(2) . . ?
C1 N21 Ni 126.2(2) . . ?
C4 N21 Ni 125.7(2) . . ?
C9 N22 C6 108.1(2) . . ?
C9 N22 Ni 126.7(2) . . ?
C6 N22 Ni 124.9(2) . . ?
N21 C1 C10 122.8(3) . 2 ?
N21 C1 C2 109.1(3) . . ?
C10 C1 C2 127.3(3) 2 . ?
C3 C2 C1 107.2(3) . . ?
C3 C2 C21 123.2(3) . . ?
C1 C2 C21 129.5(3) . . ?
C2 C3 C4 106.9(3) . . ?
C2 C3 C31 124.1(3) . . ?
C4 C3 C31 128.8(3) . . ?
N21 C4 C5 123.3(3) . . ?
N21 C4 C3 108.6(3) . . ?
C5 C4 C3 127.5(3) . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 C51 120.4(3) . . ?
C6 C5 C51 119.8(3) . . ?
N22 C6 C5 123.5(3) . . ?
N22 C6 C7 108.3(2) . . ?
C5 C6 C7 127.7(3) . . ?
C8 C7 C6 107.1(3) . . ?
C8 C7 C71 123.8(3) . . ?
C6 C7 C71 128.9(3) . . ?
C7 C8 C9 107.0(3) . . ?
C7 C8 C81 124.2(3) . . ?
C9 C8 C81 128.2(3) . . ?
N22 C9 C10 123.2(3) . . ?
N22 C9 C8 109.2(3) . . ?
C10 C9 C8 126.8(3) . . ?
C9 C10 C1 118.7(3) . 2 ?
C9 C10 C101 120.5(3) . . ?
C1 C10 C101 120.8(3) 2 . ?
C2 C21 C22 112.9(3) . . ?
C3 C31 C32 113.8(3) . . ?
C5 C51 C52 110.1(2) . . ?
C53 C52 C51 114.6(3) . . ?
C54 C53 C52 114.3(3) . . ?
C7 C71 C72 113.1(3) . . ?
C8 C81 C82 112.3(3) . . ?
C10 C101 C102 112.6(3) . . ?
C103 C102 C101 115.7(3) . . ?
C10D C103 C102 127.3(7) . . ?
C104 C103 C102 123.2(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
Ni N22 1.872(2) . ?
Ni N22 1.872(2) 2 ?
Ni N21 1.873(3) 2 ?
Ni N21 1.873(3) . ?
N21 C1 1.371(4) . ?
N21 C4 1.380(4) . ?
N22 C9 1.362(4) . ?
N22 C6 1.386(4) . ?
C1 C10 1.416(4) 2 ?
C1 C2 1.450(4) . ?
C2 C3 1.370(4) . ?
C2 C21 1.510(4) . ?
C3 C4 1.458(4) . ?
C3 C31 1.508(4) . ?
C4 C5 1.405(4) . ?
C5 C6 1.407(4) . ?
C5 C51 1.510(4) . ?
C6 C7 1.453(4) . ?
C7 C8 1.370(4) . ?
C7 C71 1.510(4) . ?
C8 C9 1.451(4) . ?
C8 C81 1.503(4) . ?
C9 C10 1.407(4) . ?
C10 C1 1.416(4) 2 ?
C10 C101 1.516(4) . ?
C21 C22 1.526(5) . ?
C31 C32 1.524(5) . ?
C51 C52 1.539(5) . ?
C52 C53 1.527(5) . ?
C53 C54 1.489(5) . ?
C71 C72 1.522(5) . ?
C81 C82 1.520(5) . ?
C101 C102 1.540(5) . ?
C102 C103 1.497(6) . ?
C103 C10D 1.301(13) . ?
C103 C104 1.456(6) . ?
