#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/39/2213972.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_2213972
loop_
_publ_author_name
'Susanta K. Nayak'
'Anirudha Jena'
'Gururaj M. Neelgund'
'S. A. Shivashankar'
'T. N. Guru Row'
_publ_section_title
;
 Bis(tert-butyl-3-oxobutanoato)dipyridinenickel(II) benzene
 solvate
;
_journal_coeditor_code           SJ2312
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1604
_journal_page_last               m1604
_journal_paper_doi               10.1107/S1600536807021496
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Ni (C8 H13 O3)2 (C5 H5 N)2] , C6 H6'
_chemical_formula_moiety         'C26 H36 N2 Ni O6 , C6 H6'
_chemical_formula_sum            'C32 H42 N2 Ni O6'
_chemical_formula_weight         609.37
_chemical_melting_point          124
_chemical_name_systematic
;
Bis(tert-butyl-3-oxobutanoato)dipyridinenickel(II) benzene solvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                99.205(2)
_cell_angle_beta                 93.504(2)
_cell_angle_gamma                117.338(2)
_cell_formula_units_Z            1
_cell_length_a                   8.3748(11)
_cell_length_b                   8.8057(12)
_cell_length_c                   12.5949(17)
_cell_measurement_reflns_used    622
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      27.983
_cell_measurement_theta_min      0.924
_cell_volume                     804.81(19)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2006) and CAMERON (Watkin et al.,
1993)
;
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8193
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.66
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  0.8763
_exptl_absorpt_correction_T_min  0.7218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'pale blue'
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.316
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3031
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0314
_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)+(0.0481P)²+0.1788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0859
_reflns_number_gt                2913
_reflns_number_total             3031
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2312.cif
_cod_data_source_block           I
_cod_database_code               2213972
_cod_database_fobs_code          2213972
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Ni Ni1 0.0000 0.0000 0.0000 0.03488(11) Uani d S 1
O O1 0.23256(15) 0.17167(15) -0.04472(10) 0.0424(3) Uani d . 1
O O2 0.14118(16) 0.04802(16) 0.15216(10) 0.0437(3) Uani d . 1
N N1 0.06342(19) -0.20147(18) -0.05506(12) 0.0405(3) Uani d . 1
O O3 0.16353(19) 0.06159(19) 0.33340(10) 0.0563(3) Uani d . 1
C C9 0.0652(2) 0.0073(2) 0.23278(14) 0.0415(4) Uani d . 1
C C6 0.2545(2) 0.1808(2) -0.14322(15) 0.0411(4) Uani d . 1
C C8 -0.1222(3) -0.0968(2) 0.23407(15) 0.0482(4) Uani d . 1
H H8 -0.1596 -0.1099 0.3016 0.058 Uiso calc R 1
C C5 -0.0671(3) -0.3621(2) -0.10124(16) 0.0500(4) Uani d . 1
H H5 -0.1875 -0.3844 -0.1075 0.060 Uiso calc R 1
C C1 0.2349(2) -0.1730(3) -0.04644(16) 0.0496(4) Uani d . 1
H H1 0.3272 -0.0617 -0.0136 0.059 Uiso calc R 1
C C11 0.3635(3) 0.1579(3) 0.35310(17) 0.0591(5) Uani d . 1
C C2 0.2816(3) -0.3003(3) -0.08382(19) 0.0611(5) Uani d . 1
H H2 0.4028 -0.2755 -0.0770 0.073 Uiso calc R 1
C C4 -0.0311(3) -0.4962(3) -0.1399(2) 0.0661(6) Uani d . 1
H H4 -0.1256 -0.6070 -0.1716 0.079 Uiso calc R 1
C C7 0.4466(3) 0.3003(3) -0.15884(19) 0.0603(5) Uani d . 1
H H7A 0.4866 0.4157 -0.1164 0.090 Uiso calc R 1
H H7B 0.4496 0.3050 -0.2344 0.090 Uiso calc R 1
H H7C 0.5256 0.2563 -0.1357 0.090 Uiso calc R 1
C C12 0.4337(4) 0.3310(3) 0.3181(2) 0.0760(7) Uani d . 1
H H12A 0.4097 0.3104 0.2402 0.114 Uiso calc R 1
H H12B 0.5624 0.3991 0.3423 0.114 Uiso calc R 1
H H12C 0.3736 0.3933 0.3497 0.114 Uiso calc R 1
C C14 0.4380(4) 0.0438(4) 0.2969(2) 0.0771(7) Uani d . 1
H H14A 0.3888 -0.0649 0.3209 0.116 Uiso calc R 1
H H14B 0.5682 0.1029 0.3148 0.116 Uiso calc R 1
H H14C 0.4041 0.0210 0.2196 0.116 Uiso calc R 1
C C3 0.1455(4) -0.4647(3) -0.1313(2) 0.0699(6) Uani d . 1
H H3 0.1728 -0.5536 -0.1574 0.084 Uiso calc R 1
C C13 0.4045(4) 0.1869(4) 0.4768(2) 0.0907(9) Uani d . 1
H H13A 0.3537 0.2568 0.5107 0.136 Uiso calc R 1
H H13B 0.5338 0.2461 0.4994 0.136 Uiso calc R 1
H H13C 0.3519 0.0760 0.4980 0.136 Uiso calc R 1
C C16 0.9918(6) 0.3375(5) 0.4840(3) 0.1279(14) Uani d D 1
H H16 0.9844 0.2273 0.4716 0.153 Uiso calc R 1
C C17 0.9913(8) 0.4253(8) 0.5856(3) 0.155(2) Uani d D 1
H H17 0.9879 0.3752 0.6457 0.186 Uiso calc R 1
C C18 1.0046(8) 0.4301(8) 0.4024(3) 0.155(2) Uani d D 1
H H18 1.0105 0.3795 0.3330 0.186 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 '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
O1 Ni1 O1 . 2 180.00(7)
O1 Ni1 O2 . 2 90.70(5)
O1 Ni1 O2 2 2 89.30(5)
O1 Ni1 O2 . . 89.30(5)
O1 Ni1 O2 2 . 90.70(5)
O2 Ni1 O2 2 . 180.00(8)
O1 Ni1 N1 . . 89.06(5)
O1 Ni1 N1 2 . 90.94(5)
O2 Ni1 N1 2 . 89.84(5)
O2 Ni1 N1 . . 90.16(5)
O1 Ni1 N1 . 2 90.94(5)
O1 Ni1 N1 2 2 89.06(5)
O2 Ni1 N1 2 2 90.16(5)
O2 Ni1 N1 . 2 89.84(5)
N1 Ni1 N1 . 2 180.00(7)
C6 O1 Ni1 . . 123.90(11)
C9 O2 Ni1 . . 123.11(11)
C5 N1 C1 . . 117.60(16)
C5 N1 Ni1 . . 120.88(12)
C1 N1 Ni1 . . 121.52(12)
C9 O3 C11 . . 122.78(15)
O2 C9 O3 . . 120.71(16)
O2 C9 C8 . . 127.34(16)
O3 C9 C8 . . 111.94(15)
O1 C6 C8 . 2 126.91(16)
O1 C6 C7 . . 114.90(16)
C8 C6 C7 2 . 118.18(17)
C6 C8 C9 2 . 125.26(17)
C6 C8 H8 2 . 117.4
C9 C8 H8 . . 117.4
N1 C5 C4 . . 122.65(19)
N1 C5 H5 . . 118.7
C4 C5 H5 . . 118.7
N1 C1 C2 . . 123.11(18)
N1 C1 H1 . . 118.4
C2 C1 H1 . . 118.4
O3 C11 C12 . . 111.15(18)
O3 C11 C14 . . 109.53(18)
C12 C11 C14 . . 112.4(2)
O3 C11 C13 . . 101.87(19)
C12 C11 C13 . . 110.6(2)
C14 C11 C13 . . 110.8(2)
C3 C2 C1 . . 118.5(2)
C3 C2 H2 . . 120.8
C1 C2 H2 . . 120.8
C3 C4 C5 . . 119.1(2)
C3 C4 H4 . . 120.4
C5 C4 H4 . . 120.4
C6 C7 H7A . . 109.5
C6 C7 H7B . . 109.5
H7A C7 H7B . . 109.5
C6 C7 H7C . . 109.5
H7A C7 H7C . . 109.5
H7B C7 H7C . . 109.5
C11 C12 H12A . . 109.5
C11 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
C11 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
C11 C14 H14A . . 109.5
C11 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
C11 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
C4 C3 C2 . . 119.06(19)
C4 C3 H3 . . 120.5
C2 C3 H3 . . 120.5
C11 C13 H13A . . 109.5
C11 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
C11 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
C17 C16 C18 . . 113.6(4)
C17 C16 H16 . . 123.2
C18 C16 H16 . . 123.2
C18 C17 C16 2_766 . 120.9(4)
C18 C17 H17 2_766 . 119.5
C16 C17 H17 . . 119.5
C17 C18 C16 2_766 . 125.4(4)
C17 C18 H18 2_766 . 117.3
C16 C18 H18 . . 117.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Ni1 O1 . 2.0243(11)
Ni1 O1 2 2.0243(11)
Ni1 O2 2 2.0626(12)
Ni1 O2 . 2.0626(12)
Ni1 N1 . 2.1041(14)
Ni1 N1 2 2.1041(14)
O1 C6 . 1.275(2)
O2 C9 . 1.245(2)
N1 C5 . 1.332(2)
N1 C1 . 1.333(2)
O3 C9 . 1.353(2)
O3 C11 . 1.470(3)
C9 C8 . 1.411(3)
C6 C8 2 1.380(3)
C6 C7 . 1.512(2)
C8 C6 2 1.380(3)
C8 H8 . 0.9300
C5 C4 . 1.371(3)
C5 H5 . 0.9300
C1 C2 . 1.375(3)
C1 H1 . 0.9300
C11 C12 . 1.512(3)
C11 C14 . 1.517(3)
C11 C13 . 1.529(3)
C2 C3 . 1.370(3)
C2 H2 . 0.9300
C4 C3 . 1.368(3)
C4 H4 . 0.9300
C7 H7A . 0.9600
C7 H7B . 0.9600
C7 H7C . 0.9600
C12 H12A . 0.9600
C12 H12B . 0.9600
C12 H12C . 0.9600
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 0.9600
C3 H3 . 0.9300
C13 H13A . 0.9600
C13 H13B . 0.9600
C13 H13C . 0.9600
C16 C17 . 1.387(6)
C16 C18 . 1.391(6)
C16 H16 . 0.9300
C17 C18 2_766 1.243(6)
C17 H17 . 0.9300
C18 C17 2_766 1.243(6)
C18 H18 . 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
O2 Ni1 O1 C6 2 . -16.16(13)
O2 Ni1 O1 C6 . . 163.84(13)
N1 Ni1 O1 C6 . . 73.67(13)
N1 Ni1 O1 C6 2 . -106.33(13)
O1 Ni1 O2 C9 . . 163.87(13)
O1 Ni1 O2 C9 2 . -16.13(13)
N1 Ni1 O2 C9 . . -107.07(13)
N1 Ni1 O2 C9 2 . 72.93(13)
O1 Ni1 N1 C5 . . -144.94(14)
O1 Ni1 N1 C5 2 . 35.06(14)
O2 Ni1 N1 C5 2 . -54.24(14)
O2 Ni1 N1 C5 . . 125.76(14)
O1 Ni1 N1 C1 . . 34.18(14)
O1 Ni1 N1 C1 2 . -145.82(14)
O2 Ni1 N1 C1 2 . 124.88(14)
O2 Ni1 N1 C1 . . -55.12(14)
Ni1 O2 C9 O3 . . -171.36(12)
Ni1 O2 C9 C8 . . 9.6(2)
C11 O3 C9 O2 . . -5.1(3)
C11 O3 C9 C8 . . 174.11(17)
Ni1 O1 C6 C8 . 2 9.6(2)
Ni1 O1 C6 C7 . . -171.77(12)
O2 C9 C8 C6 . 2 3.9(3)
O3 C9 C8 C6 . 2 -175.27(17)
C1 N1 C5 C4 . . -0.4(3)
Ni1 N1 C5 C4 . . 178.80(16)
C5 N1 C1 C2 . . 0.7(3)
Ni1 N1 C1 C2 . . -178.42(16)
C9 O3 C11 C12 . . 62.2(2)
C9 O3 C11 C14 . . -62.7(2)
C9 O3 C11 C13 . . 179.96(19)
N1 C1 C2 C3 . . -0.6(3)
N1 C5 C4 C3 . . -0.2(3)
C5 C4 C3 C2 . . 0.3(4)
C1 C2 C3 C4 . . 0.0(4)
C18 C16 C17 C18 . 2_766 2.4(10)
C17 C16 C18 C17 . 2_766 -2.6(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139072343
