#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/01/4300170.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_4300170
loop_
_publ_author_name
'Pamela A. Lord'
'Marilyn M. Olmstead'
'Alan L. Balch'
_publ_section_title
;
Redox Characteristics of Nickel and Palladium Complexes of the Open-Chain
Tetrapyrrole Octaethylbilindione: A Biliverdin Model
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1128
_journal_page_last               1134
_journal_paper_doi               10.1021/ic9910209
_journal_volume                  39
_journal_year                    2000
_chemical_formula_sum            'C35 H43 I3 N4 Ni O2'
_chemical_formula_weight         991.14
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.121(3)
_cell_length_b                   16.777(3)
_cell_length_c                   14.628(3)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      29.9
_cell_measurement_theta_min      5.2
_cell_volume                     3710.9(12)
_computing_cell_refinement       'Siemens P3'
_computing_data_collection       'Siemens P3'
_computing_data_reduction        'Siemens XDISK'
_computing_molecular_graphics    'SHELXTL 5.03, XP (Sheldrick, 1994)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Syntex P2₁'
_diffrn_measurement_method       2θ-ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            4964
_diffrn_reflns_theta_full        67.03
_diffrn_reflns_theta_max         67.03
_diffrn_reflns_theta_min         3.94
_diffrn_standards_decay_%        <0.1
_diffrn_standards_interval_count 198
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    20.624
_exptl_absorpt_correction_T_max  0.2892
_exptl_absorpt_correction_T_min  0.0540
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;XABS2: an empirical absorption correction program. Parkin, S.; Moezzi,
 B.; Hope, H. J. Appl. Cryst. 1995, 28, 53-56.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.680
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0688P)²+7.0729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1359
_reflns_number_gt                2643
_reflns_number_total             3311
_reflns_threshold_expression     >2sigma(I)
_cod_original_cell_volume        3710.9(13)
_cod_database_code               4300170
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni 0.5000 0.40213(7) 0.2500 0.0134(3) Uani 1 2 d S . .
I1 I 0.0000 0.42818(3) 0.2500 0.0387(2) Uani 1 2 d S . .
I2 I 0.18487(4) 0.42659(3) 0.31086(4) 0.04739(19) Uani 1 1 d . . .
C1 C 0.4081(4) 0.5554(3) 0.2818(4) 0.0178(12) Uani 1 1 d . . .
C2 C 0.3753(4) 0.6028(3) 0.3601(4) 0.0178(12) Uani 1 1 d . . .
C3 C 0.3786(4) 0.5569(3) 0.4347(4) 0.0170(11) Uani 1 1 d . . .
C4 C 0.4180(3) 0.4792(3) 0.4057(4) 0.0159(11) Uani 1 1 d . . .
C5 C 0.4256(4) 0.4125(3) 0.4632(4) 0.0164(11) Uani 1 1 d . . .
H5 H 0.4144 0.4182 0.5268 0.020 Uiso 1 1 calc R . .
C6 C 0.4489(4) 0.3386(3) 0.4290(4) 0.0164(11) Uani 1 1 d . . .
C7 C 0.4500(4) 0.2641(3) 0.4815(4) 0.0180(12) Uani 1 1 d . . .
C8 C 0.4697(4) 0.2053(3) 0.4203(4) 0.0163(12) Uani 1 1 d . . .
C9 C 0.4834(3) 0.2431(3) 0.3318(4) 0.0152(12) Uani 1 1 d . . .
C10 C 0.5000 0.2043(4) 0.2500 0.0144(15) Uani 1 2 d S . .
H10 H 0.5000 0.1476 0.2500 0.017 Uiso 1 2 calc SR . .
C11 C 0.3385(4) 0.6860(3) 0.3470(5) 0.0214(13) Uani 1 1 d . . .
H11A H 0.3736 0.7140 0.2998 0.026 Uiso 1 1 calc R . .
H11B H 0.3441 0.7161 0.4049 0.026 Uiso 1 1 calc R . .
C12 C 0.2416(4) 0.6844(4) 0.3180(6) 0.0357(17) Uani 1 1 d . . .
H12A H 0.2356 0.6540 0.2612 0.054 Uiso 1 1 calc R . .
H12B H 0.2208 0.7391 0.3081 0.054 Uiso 1 1 calc R . .
H12C H 0.2061 0.6592 0.3661 0.054 Uiso 1 1 calc R . .
C13 C 0.3465(4) 0.5733(3) 0.5304(4) 0.0206(12) Uani 1 1 d . . .
H13A H 0.3421 0.6316 0.5400 0.025 Uiso 1 1 calc R . .
H13B H 0.3895 0.5518 0.5750 0.025 Uiso 1 1 calc R . .
C14 C 0.2550(4) 0.5345(4) 0.5463(5) 0.0257(14) Uani 1 1 d . . .
H14A H 0.2118 0.5578 0.5040 0.039 Uiso 1 1 calc R . .
H14B H 0.2361 0.5443 0.6094 0.039 Uiso 1 1 calc R . .
H14C H 0.2591 0.4770 0.5356 0.039 Uiso 1 1 calc R . .
C15 C 0.4213(4) 0.2564(3) 0.5787(4) 0.0237(13) Uani 1 1 d . . .
H15A H 0.4432 0.3028 0.6138 0.028 Uiso 1 1 calc R . .
H15B H 0.4481 0.2078 0.6054 0.028 Uiso 1 1 calc R . .
C16 C 0.3217(5) 0.2516(5) 0.5880(6) 0.0397(18) Uani 1 1 d . . .
H16A H 0.2953 0.3023 0.5692 0.059 Uiso 1 1 calc R . .
H16B H 0.3062 0.2405 0.6518 0.059 Uiso 1 1 calc R . .
H16C H 0.2992 0.2087 0.5489 0.059 Uiso 1 1 calc R . .
C17 C 0.4802(4) 0.1177(3) 0.4380(5) 0.0198(13) Uani 1 1 d . . .
H17A H 0.4464 0.0875 0.3915 0.024 Uiso 1 1 calc R . .
H17B H 0.4553 0.1048 0.4988 0.024 Uiso 1 1 calc R . .
C18 C 0.5772(4) 0.0919(4) 0.4348(5) 0.0314(15) Uani 1 1 d . . .
H18A H 0.6015 0.1030 0.3740 0.047 Uiso 1 1 calc R . .
H18B H 0.5814 0.0347 0.4475 0.047 Uiso 1 1 calc R . .
H18C H 0.6109 0.1216 0.4808 0.047 Uiso 1 1 calc R . .
O1 O 0.4071(3) 0.5716(2) 0.2021(3) 0.0217(9) Uani 1 1 d . . .
N1 N 0.4396(3) 0.4790(3) 0.3181(4) 0.0154(10) Uani 1 1 d . . .
N2 N 0.4723(3) 0.3248(3) 0.3384(3) 0.0153(10) Uani 1 1 d . . .
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'
O O 0.0492 0.0322 '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'
I I -0.3257 6.8362 '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
N1 Ni N1 92.7(3) 3_655 . ?
N1 Ni N2 90.0(2) 3_655 3_655 ?
N1 Ni N2 162.3(2) . 3_655 ?
N1 Ni N2 162.3(2) 3_655 . ?
N1 Ni N2 90.0(2) . . ?
N2 Ni N2 92.7(3) 3_655 . ?
I2 I1 I2 178.95(3) 3 . ?
O1 C1 N1 123.6(5) . . ?
O1 C1 C2 128.9(5) . . ?
N1 C1 C2 107.4(5) . . ?
C3 C2 C1 108.0(5) . . ?
C3 C2 C11 130.5(6) . . ?
C1 C2 C11 121.3(5) . . ?
C2 C3 C4 106.6(5) . . ?
C2 C3 C13 129.8(5) . . ?
C4 C3 C13 123.5(5) . . ?
N1 C4 C5 123.9(5) . . ?
N1 C4 C3 112.1(5) . . ?
C5 C4 C3 123.9(5) . . ?
C6 C5 C4 121.3(6) . . ?
C5 C6 N2 123.9(5) . . ?
C5 C6 C7 125.3(6) . . ?
N2 C6 C7 110.7(5) . . ?
C8 C7 C6 106.0(5) . . ?
C8 C7 C15 128.7(5) . . ?
C6 C7 C15 124.7(5) . . ?
C7 C8 C9 107.4(5) . . ?
C7 C8 C17 128.2(6) . . ?
C9 C8 C17 124.3(5) . . ?
N2 C9 C10 123.3(6) . . ?
N2 C9 C8 110.6(5) . . ?
C10 C9 C8 126.1(5) . . ?
C9 C10 C9 123.9(7) 3_655 . ?
C2 C11 C12 111.9(5) . . ?
C3 C13 C14 110.6(5) . . ?
C7 C15 C16 112.2(6) . . ?
C8 C17 C18 111.9(5) . . ?
C4 N1 C1 105.5(5) . . ?
C4 N1 Ni 129.8(4) . . ?
C1 N1 Ni 124.7(4) . . ?
C9 N2 C6 105.2(5) . . ?
C9 N2 Ni 127.5(4) . . ?
C6 N2 Ni 126.7(4) . . ?
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 N1 1.867(5) 3_655 ?
Ni N1 1.867(5) . ?
Ni N2 1.879(5) 3_655 ?
Ni N2 1.879(5) . ?
I1 I2 2.9338(8) 3 ?
I1 I2 2.9338(8) . ?
C1 O1 1.198(7) . ?
C1 N1 1.468(7) . ?
C1 C2 1.481(8) . ?
C2 C3 1.337(8) . ?
C2 C11 1.513(7) . ?
C3 C4 1.495(7) . ?
C3 C13 1.506(8) . ?
C4 N1 1.322(8) . ?
C4 C5 1.405(8) . ?
C5 C6 1.382(8) . ?
C6 N2 1.392(8) . ?
C6 C7 1.466(8) . ?
C7 C8 1.365(8) . ?
C7 C15 1.493(8) . ?
C8 C9 1.457(8) . ?
C8 C17 1.501(7) . ?
C9 N2 1.384(7) . ?
C9 C10 1.385(7) . ?
C10 C9 1.385(7) 3_655 ?
C11 C12 1.525(9) . ?
C13 C14 1.547(8) . ?
C15 C16 1.514(9) . ?
C17 C18 1.530(8) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139126118
