#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:33:07 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301779 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/39/1543945.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_1543945
loop_
_publ_author_name
'Na Xing'
'Li Ting Xu'
'Feng Ying Bai'
'Hui Shan'
'Yong Heng Xing'
'Zhan Shi'
_publ_section_title
;
 Synthesis and characterization of novel transition metal complexes with
 indole acetic acid ligands: Evaluation of their catalytic activity for
 the oxidation of cyclohexane
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              360
_journal_page_last               366
_journal_paper_doi               10.1016/j.ica.2013.09.004
_journal_volume                  409B
_journal_year                    2014
_chemical_formula_sum            'C32 H26 N4 Ni O5'
_chemical_formula_weight         605.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 103.91(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.097(3)
_cell_length_b                   12.836(3)
_cell_length_c                   16.875(3)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      3.06
_cell_volume                     2753.7(11)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_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  0.0618
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26412
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  0.9149
_exptl_absorpt_correction_T_min  0.8576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         6264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0352P)²+1.4291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.1002
_reflns_number_gt                4673
_reflns_number_total             6264
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2014-409B-360-366-1.cif
_cod_data_source_block           bai-736
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 4624 2016-04-14 12:54:50Z antanas 

The following automatic conversions were performed:

'_journal_paper_doi' value
'http://dx.doi.org/10.1016/j.ica.2013.09.004' was changed to
'10.1016/j.ica.2013.09.004'.

Automatic conversion script
Id: cif_fix_values 6433 2018-09-21 13:16:33Z andrius 
;
_cod_original_cell_volume        2753.7(10)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1543945
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H4A H 0.217(3) 0.351(3) 0.669(3) 0.101(14) Uiso 1 1 d . . .
H3A H 0.806(3) -0.299(3) 0.704(2) 0.084(13) Uiso 1 1 d . . .
Ni1 Ni 0.67282(2) 0.08353(2) 0.971415(17) 0.02544(9) Uani 1 1 d . . .
O1 O 0.54713(11) -0.01756(13) 0.91134(10) 0.0311(4) Uani 1 1 d . . .
O2 O 0.69330(12) -0.00567(15) 0.87091(11) 0.0382(4) Uani 1 1 d . . .
O3 O 0.62538(13) 0.20866(14) 0.89594(10) 0.0372(4) Uani 1 1 d . . .
O4 O 0.51304(15) 0.28559(17) 0.95763(12) 0.0531(6) Uani 1 1 d . . .
O5W O 0.60508(12) 0.14445(14) 1.05948(10) 0.0304(4) Uani 1 1 d . . .
H5WA H 0.5686 0.1947 1.0408 0.046 Uiso 1 1 calc R . .
H5WB H 0.560(3) 0.100(3) 1.070(2) 0.066(11) Uiso 1 1 d . . .
N1 N 0.82481(14) 0.13895(17) 1.00945(12) 0.0314(5) Uani 1 1 d . . .
N2 N 0.73943(15) -0.03535(16) 1.05138(12) 0.0311(5) Uani 1 1 d . . .
N3 N 0.7718(2) -0.2872(2) 0.73782(17) 0.0543(7) Uani 1 1 d . . .
N4 N 0.2711(2) 0.3741(2) 0.71551(16) 0.0586(7) Uani 1 1 d . . .
C1 C 0.8654(2) 0.2261(2) 0.98761(18) 0.0456(7) Uani 1 1 d . . .
H1A H 0.8207 0.2746 0.9560 0.055 Uiso 1 1 calc R . .
C2 C 0.9735(2) 0.2475(3) 1.0105(2) 0.0628(10) Uani 1 1 d . . .
H2A H 0.9996 0.3087 0.9935 0.075 Uiso 1 1 calc R . .
C3 C 1.0398(2) 0.1783(3) 1.0579(2) 0.0633(10) Uani 1 1 d . . .
H3B H 1.1116 0.1919 1.0727 0.076 Uiso 1 1 calc R . .
C4 C 1.00060(19) 0.0869(3) 1.08424(18) 0.0499(8) Uani 1 1 d . . .
C5 C 1.0623(2) 0.0111(3) 1.1375(2) 0.0637(11) Uani 1 1 d . . .
H5A H 1.1346 0.0206 1.1554 0.076 Uiso 1 1 calc R . .
C6 C 1.0177(2) -0.0730(3) 1.1617(2) 0.0656(10) Uani 1 1 d . . .
H6A H 1.0598 -0.1196 1.1974 0.079 Uiso 1 1 calc R . .
C7 C 0.9071(2) -0.0938(3) 1.13451(17) 0.0488(8) Uani 1 1 d . . .
C8 C 0.8550(3) -0.1812(3) 1.1569(2) 0.0642(9) Uani 1 1 d . . .
H8A H 0.8930 -0.2308 1.1922 0.077 Uiso 1 1 calc R . .
C9 C 0.7502(3) -0.1935(3) 1.1274(2) 0.0588(8) Uani 1 1 d . . .
H9A H 0.7158 -0.2509 1.1422 0.071 Uiso 1 1 calc R . .
C10 C 0.6948(2) -0.1186(2) 1.07445(17) 0.0423(6) Uani 1 1 d . . .
H10A H 0.6227 -0.1276 1.0543 0.051 Uiso 1 1 calc R . .
C11 C 0.84473(18) -0.0225(2) 1.08119(15) 0.0332(6) Uani 1 1 d . . .
C12 C 0.89079(18) 0.0696(2) 1.05725(15) 0.0337(6) Uani 1 1 d . . .
C13 C 0.60598(18) -0.0486(2) 0.86571(15) 0.0326(6) Uani 1 1 d . . .
C14 C 0.5689(2) -0.1350(2) 0.80502(18) 0.0481(7) Uani 1 1 d . . .
H14A H 0.5156 -0.1750 0.8228 0.058 Uiso 1 1 calc R . .
H14B H 0.5358 -0.1041 0.7527 0.058 Uiso 1 1 calc R . .
C15 C 0.6533(2) -0.2081(2) 0.79327(17) 0.0412(7) Uani 1 1 d . . .
C16 C 0.6998(2) -0.2086(2) 0.72929(18) 0.0500(8) Uani 1 1 d . . .
H16A H 0.6846 -0.1620 0.6859 0.060 Uiso 1 1 calc R . .
C17 C 0.7740(2) -0.3389(2) 0.80870(19) 0.0482(7) Uani 1 1 d . . .
C18 C 0.8353(3) -0.4216(3) 0.8457(3) 0.0732(10) Uani 1 1 d . . .
H18A H 0.8836 -0.4534 0.8211 0.088 Uiso 1 1 calc R . .
C19 C 0.8220(4) -0.4556(3) 0.9210(3) 0.0910(14) Uani 1 1 d . . .
H19A H 0.8625 -0.5107 0.9474 0.109 Uiso 1 1 calc R . .
C20 C 0.7493(4) -0.4083(3) 0.9573(3) 0.0882(13) Uani 1 1 d . . .
H20A H 0.7428 -0.4320 1.0080 0.106 Uiso 1 1 calc R . .
C21 C 0.6875(3) -0.3286(3) 0.9209(2) 0.0654(10) Uani 1 1 d . . .
H21A H 0.6379 -0.2992 0.9454 0.079 Uiso 1 1 calc R . .
C22 C 0.6999(2) -0.2912(2) 0.84568(17) 0.0436(7) Uani 1 1 d . . .
C23 C 0.56121(19) 0.2808(2) 0.90285(16) 0.0380(6) Uani 1 1 d . . .
C24 C 0.5449(2) 0.3686(3) 0.8395(2) 0.0561(9) Uani 1 1 d . . .
H24A H 0.5770 0.4318 0.8656 0.067 Uiso 1 1 calc R . .
H24B H 0.5805 0.3503 0.7972 0.067 Uiso 1 1 calc R . .
C25 C 0.4318(2) 0.3894(2) 0.80086(17) 0.0425(7) Uani 1 1 d . . .
C26 C 0.3734(3) 0.3386(3) 0.73460(19) 0.0565(8) Uani 1 1 d . . .
H26A H 0.3991 0.2869 0.7060 0.068 Uiso 1 1 calc R . .
C27 C 0.2634(2) 0.4512(2) 0.76950(18) 0.0452(7) Uani 1 1 d . . .
C28 C 0.1776(2) 0.5111(3) 0.7759(3) 0.0688(11) Uani 1 1 d . . .
H28A H 0.1127 0.5031 0.7391 0.083 Uiso 1 1 calc R . .
C29 C 0.1911(3) 0.5816(3) 0.8374(3) 0.0836(13) Uani 1 1 d . . .
H29A H 0.1337 0.6205 0.8439 0.100 Uiso 1 1 calc R . .
C30 C 0.2879(3) 0.5971(3) 0.8906(3) 0.0778(12) Uani 1 1 d . . .
H30A H 0.2947 0.6482 0.9306 0.093 Uiso 1 1 calc R . .
C31 C 0.3749(3) 0.5387(3) 0.8861(2) 0.0569(8) Uani 1 1 d . . .
H31A H 0.4396 0.5493 0.9227 0.068 Uiso 1 1 calc R . .
C32 C 0.3628(2) 0.4625(2) 0.82442(16) 0.0380(6) 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 0.0033 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'
N N 0.0061 0.0033 '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
O3 Ni1 O5W 91.83(7) . .
O3 Ni1 N1 92.79(8) . .
O5W Ni1 N1 101.26(7) . .
O3 Ni1 N2 172.94(7) . .
O5W Ni1 N2 89.81(7) . .
N1 Ni1 N2 80.15(8) . .
O3 Ni1 O2 90.22(7) . .
O5W Ni1 O2 160.63(7) . .
N1 Ni1 O2 97.88(7) . .
N2 Ni1 O2 90.51(8) . .
O3 Ni1 O1 95.54(7) . .
O5W Ni1 O1 98.95(6) . .
N1 Ni1 O1 157.85(7) . .
N2 Ni1 O1 90.99(8) . .
O2 Ni1 O1 61.68(6) . .
C13 O1 Ni1 88.15(13) . .
C13 O2 Ni1 90.26(14) . .
C23 O3 Ni1 128.32(16) . .
C1 N1 C12 118.4(2) . .
C1 N1 Ni1 128.63(19) . .
C12 N1 Ni1 112.69(16) . .
C10 N2 C11 118.1(2) . .
C10 N2 Ni1 129.56(17) . .
C11 N2 Ni1 112.35(17) . .
C17 N3 C16 108.7(2) . .
C27 N4 C26 107.9(3) . .
N1 C1 C2 122.2(3) . .
C3 C2 C1 119.7(3) . .
C2 C3 C4 120.3(3) . .
C3 C4 C12 116.8(3) . .
C3 C4 C5 125.1(3) . .
C12 C4 C5 118.0(3) . .
C6 C5 C4 121.2(3) . .
C5 C6 C7 122.3(3) . .
C11 C7 C8 116.6(3) . .
C11 C7 C6 118.1(3) . .
C8 C7 C6 125.3(3) . .
C9 C8 C7 120.5(3) . .
C8 C9 C10 118.9(3) . .
N2 C10 C9 123.2(3) . .
N2 C11 C7 122.8(3) . .
N2 C11 C12 117.1(2) . .
C7 C11 C12 120.1(2) . .
N1 C12 C4 122.5(3) . .
N1 C12 C11 117.2(2) . .
C4 C12 C11 120.2(3) . .
O2 C13 O1 119.6(2) . .
O2 C13 C14 120.7(2) . .
O1 C13 C14 119.7(2) . .
C15 C14 C13 115.0(2) . .
C16 C15 C22 106.4(3) . .
C16 C15 C14 126.3(3) . .
C22 C15 C14 127.2(2) . .
C15 C16 N3 110.5(3) . .
N3 C17 C18 131.1(3) . .
N3 C17 C22 107.7(3) . .
C18 C17 C22 121.2(3) . .
C17 C18 C19 117.7(4) . .
C20 C19 C18 121.0(4) . .
C21 C20 C19 121.8(4) . .
C20 C21 C22 118.8(4) . .
C21 C22 C17 119.5(3) . .
C21 C22 C15 133.8(3) . .
C17 C22 C15 106.7(2) . .
O4 C23 O3 124.7(2) . .
O4 C23 C24 118.3(2) . .
O3 C23 C24 117.0(2) . .
C25 C24 C23 113.2(2) . .
C26 C25 C32 106.0(3) . .
C26 C25 C24 125.2(3) . .
C32 C25 C24 128.8(3) . .
C25 C26 N4 110.9(3) . .
N4 C27 C28 130.1(3) . .
N4 C27 C32 107.9(3) . .
C28 C27 C32 121.9(3) . .
C29 C28 C27 118.0(3) . .
C28 C29 C30 121.6(4) . .
C29 C30 C31 121.8(4) . .
C30 C31 C32 118.0(3) . .
C31 C32 C27 118.6(3) . .
C31 C32 C25 134.2(3) . .
C27 C32 C25 107.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O3 2.0513(18) .
Ni1 O5W 2.0595(16) .
Ni1 N1 2.0654(19) .
Ni1 N2 2.084(2) .
Ni1 O2 2.1161(17) .
Ni1 O1 2.1492(17) .
O1 C13 1.277(3) .
O2 C13 1.253(3) .
O3 C23 1.275(3) .
O4 C23 1.240(3) .
N1 C1 1.329(3) .
N1 C12 1.362(3) .
N2 C10 1.321(3) .
N2 C11 1.360(3) .
N3 C17 1.363(4) .
N3 C16 1.364(4) .
N4 C27 1.365(4) .
N4 C26 1.378(4) .
C1 C2 1.401(4) .
C2 C3 1.359(5) .
C3 C4 1.396(5) .
C4 C12 1.418(3) .
C4 C5 1.434(5) .
C5 C6 1.338(5) .
C6 C7 1.436(4) .
C7 C11 1.400(4) .
C7 C8 1.411(5) .
C8 C9 1.352(5) .
C9 C10 1.392(4) .
C11 C12 1.429(4) .
C13 C14 1.509(4) .
C14 C15 1.499(4) .
C15 C16 1.361(4) .
C15 C22 1.425(4) .
C17 C18 1.385(5) .
C17 C22 1.414(4) .
C18 C19 1.394(6) .
C19 C20 1.390(6) .
C20 C21 1.356(5) .
C21 C22 1.403(4) .
C23 C24 1.532(4) .
C24 C25 1.492(4) .
C25 C26 1.360(4) .
C25 C32 1.425(4) .
C27 C28 1.387(4) .
C27 C32 1.412(4) .
C28 C29 1.356(6) .
C29 C30 1.381(6) .
C30 C31 1.382(5) .
C31 C32 1.410(4) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5W H5WA O4 0.8200 1.8400 2.587(3) 152.00 . yes
O5W H5WB O1 0.87(4) 1.84(4) 2.710(2) 173(4) 3_657 yes
N3 H3A O3 0.82(4) 2.10(4) 2.894(3) 165(4) 2_646 yes
N4 H4A O5W 0.97(5) 2.07(5) 2.994(3) 160(3) 4_454 yes
C5 H5A O2 0.9300 2.4100 3.239(3) 149.00 3_757 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168302660
