#------------------------------------------------------------------------------
#$Date: 2021-12-09 11:47:29 +0100 (Thu 09 de Dec de 2021) $
#$Revision: 271310 $
#$URL: svn://www.crystallography.net/cod/cif/1/56/56/1565639.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_1565639
loop_
_publ_author_name
'Layek, Samaresh'
'Agrahari, Bhumika'
'Kumar, Akash'
'Dege, Necmi'
'Pathak, Devendra D.'
_publ_section_title
;
 Synthesis and X-ray crystal structures of three new nickel(II) complexes
 of benzoylhydrazones: Catalytic applications in the synthesis of
 2-arylbenzoxazoles
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119222
_journal_paper_doi               10.1016/j.ica.2019.119222
_journal_volume                  500
_journal_year                    2020
_chemical_formula_sum            'C24 H19 N3 Ni O2'
_chemical_formula_weight         440.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 95.678(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1370(8)
_cell_length_b                   6.0223(3)
_cell_length_c                   21.6711(10)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      66.2627
_cell_measurement_theta_min      3.4088
_cell_volume                     1965.84(17)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Bruker AXS Inc., 2015)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0870
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            31918
_diffrn_reflns_theta_full        66.46
_diffrn_reflns_theta_max         66.46
_diffrn_reflns_theta_min         3.41
_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_source_type              'Bruker Kappa Duo APEX2'
_exptl_absorpt_coefficient_mu    1.639
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.570
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0313
_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)+(0.0660P)²+0.3588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                2898
_reflns_number_total             3435
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ICA-2020-500-119222.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_database_code               1565639
loop_
_space_group_symop_operation_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_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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni1 0.42645(2) 0.32380(4) 0.23640(2) 0.03665(15) Uani d . . . 1 . .
C C1 0.52708(13) -0.0276(3) 0.24207(9) 0.0378(4) Uani d . . . 1 . .
C C2 0.58472(13) -0.2049(3) 0.22092(9) 0.0381(5) Uani d . . . 1 . .
C C3 0.61100(15) -0.1966(3) 0.16138(10) 0.0494(6) Uani d . . . 1 . .
H H3 0.5919 -0.0806 0.135 0.059 Uiso calc U . R 1 . .
C C4 0.66533(16) -0.3598(4) 0.14119(11) 0.0592(6) Uani d . . . 1 . .
H H4 0.6834 -0.3518 0.1015 0.071 Uiso calc U . R 1 . .
C C5 0.69287(16) -0.5338(4) 0.17926(11) 0.0583(6) Uani d . . . 1 . .
H H5 0.7291 -0.6441 0.1653 0.07 Uiso calc U . R 1 . .
C C6 0.66646(16) -0.5441(3) 0.23842(11) 0.0543(6) Uani d . . . 1 . .
H H6 0.6853 -0.6611 0.2645 0.065 Uiso calc U . R 1 . .
C C7 0.61232(14) -0.3817(3) 0.25898(9) 0.0448(5) Uani d . . . 1 . .
H H7 0.5942 -0.3909 0.2987 0.054 Uiso calc U . R 1 . .
C C8 0.44248(13) 0.2179(3) 0.36370(9) 0.0389(4) Uani d . . . 1 . .
H H8 0.4638 0.1217 0.3953 0.047 Uiso calc U . R 1 . .
C C9 0.39235(12) 0.4057(3) 0.37999(8) 0.0363(4) Uani d . . . 1 . .
C C10 0.35745(12) 0.5537(3) 0.33371(9) 0.0390(5) Uani d . . . 1 . .
C C11 0.31428(13) 0.7521(3) 0.35098(9) 0.0443(5) Uani d . . . 1 . .
H H11 0.2896 0.848 0.3203 0.053 Uiso calc U . R 1 . .
C C12 0.30895(14) 0.8021(3) 0.41138(10) 0.0442(5) Uani d . . . 1 . .
H H12 0.283 0.9355 0.4215 0.053 Uiso calc U . R 1 . .
C C13 0.34199(14) 0.6564(3) 0.45977(10) 0.0408(5) Uani d . . . 1 . .
C C14 0.33527(14) 0.7103(3) 0.52252(10) 0.0480(5) Uani d . . . 1 . .
H H14 0.3104 0.8455 0.5323 0.058 Uiso calc U . R 1 . .
C C15 0.36426(15) 0.5691(4) 0.56890(9) 0.0535(6) Uani d . . . 1 . .
H H15 0.3595 0.6078 0.61 0.064 Uiso calc U . R 1 . .
C C16 0.40136(16) 0.3647(4) 0.55461(10) 0.0522(6) Uani d . . . 1 . .
H H16 0.4203 0.2663 0.5862 0.063 Uiso calc U . R 1 . .
C C17 0.40984(14) 0.3092(3) 0.49388(9) 0.0458(5) Uani d . . . 1 . .
H H17 0.4348 0.173 0.4852 0.055 Uiso calc U . R 1 . .
C C18 0.38176(12) 0.4530(3) 0.44442(9) 0.0379(4) Uani d . . . 1 . .
C C19 0.36384(14) 0.6809(3) 0.15400(10) 0.0419(5) Uani d . . . 1 . .
H H19 0.3466 0.7454 0.1899 0.05 Uiso calc U . R 1 . .
C C20 0.34999(15) 0.7965(3) 0.09952(10) 0.0446(5) Uani d . . . 1 . .
H H20 0.3243 0.9368 0.0994 0.054 Uiso calc U . R 1 . .
C C21 0.37372(14) 0.7077(3) 0.04455(10) 0.0440(5) Uani d . . . 1 . .
C C22 0.3605(2) 0.8319(4) -0.01579(11) 0.0680(7) Uani d . . . 1 . .
H H22A 0.4 0.7738 -0.0439 0.102 Uiso calc U . R 1 . .
H H22B 0.373 0.9866 -0.0085 0.102 Uiso calc U . R 1 . .
H H22C 0.3002 0.8148 -0.0335 0.102 Uiso calc U . R 1 . .
C C23 0.41079(14) 0.4967(3) 0.04876(9) 0.0474(5) Uani d . . . 1 . .
H H23 0.4271 0.4276 0.0132 0.057 Uiso calc U . R 1 . .
C C24 0.42362(14) 0.3893(3) 0.10445(9) 0.0441(5) Uani d . . . 1 . .
H H24 0.4489 0.2485 0.1056 0.053 Uiso calc U . R 1 . .
N N1 0.46036(11) 0.1721(2) 0.30766(7) 0.0370(4) Uani d . . . 1 . .
N N2 0.51532(11) -0.0125(2) 0.30098(7) 0.0412(4) Uani d . . . 1 . .
N N3 0.40118(10) 0.4787(2) 0.15790(7) 0.0367(4) Uani d . . . 1 . .
O O1 0.49154(9) 0.1104(2) 0.20052(6) 0.0416(3) Uani d . . . 1 . .
O O2 0.36162(9) 0.5268(2) 0.27392(6) 0.0452(4) Uani d . . . 1 . .
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'
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
O2 Ni1 N1 . . 94.45(6)
O2 Ni1 O1 . . 177.91(5)
N1 Ni1 O1 . . 83.70(6)
O2 Ni1 N3 . . 90.02(6)
N1 Ni1 N3 . . 174.60(6)
O1 Ni1 N3 . . 91.88(6)
O1 C1 N2 . . 122.90(16)
O1 C1 C2 . . 117.52(16)
N2 C1 C2 . . 119.56(17)
C7 C2 C3 . . 118.94(17)
C7 C2 C1 . . 121.48(16)
C3 C2 C1 . . 119.57(17)
C4 C3 C2 . . 120.2(2)
C5 C4 C3 . . 120.5(2)
C4 C5 C6 . . 119.56(19)
C7 C6 C5 . . 120.3(2)
C6 C7 C2 . . 120.45(18)
N1 C8 C9 . . 124.38(18)
C10 C9 C8 . . 119.88(16)
C10 C9 C18 . . 119.55(16)
C8 C9 C18 . . 120.46(17)
O2 C10 C9 . . 125.06(16)
O2 C10 C11 . . 115.41(17)
C9 C10 C11 . . 119.52(16)
C12 C11 C10 . . 120.77(19)
C11 C12 C13 . . 121.78(17)
C14 C13 C18 . . 119.81(19)
C14 C13 C12 . . 121.05(17)
C18 C13 C12 . . 119.14(18)
C15 C14 C13 . . 121.41(18)
C14 C15 C16 . . 119.65(19)
C17 C16 C15 . . 120.2(2)
C16 C17 C18 . . 121.85(18)
C17 C18 C13 . . 117.05(17)
C17 C18 C9 . . 123.89(16)
C13 C18 C9 . . 119.05(18)
N3 C19 C20 . . 122.92(18)
C19 C20 C21 . . 120.99(17)
C20 C21 C23 . . 115.74(18)
C20 C21 C22 . . 122.19(18)
C23 C21 C22 . . 122.07(19)
C24 C23 C21 . . 120.84(18)
N3 C24 C23 . . 122.89(17)
C8 N1 N2 . . 116.37(16)
C8 N1 Ni1 . . 128.17(13)
N2 N1 Ni1 . . 115.42(11)
C1 N2 N1 . . 107.13(15)
C19 N3 C24 . . 116.61(17)
C19 N3 Ni1 . . 122.39(13)
C24 N3 Ni1 . . 120.96(13)
C1 O1 Ni1 . . 110.84(11)
C10 O2 Ni1 . . 127.40(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Ni1 O2 . 1.8104(12)
Ni1 N1 . 1.8236(16)
Ni1 O1 . 1.8382(12)
Ni1 N3 . 1.9447(15)
C1 O1 . 1.302(2)
C1 N2 . 1.309(2)
C1 C2 . 1.480(2)
C2 C7 . 1.386(3)
C2 C3 . 1.388(3)
C3 C4 . 1.380(3)
C4 C5 . 1.373(3)
C5 C6 . 1.381(3)
C6 C7 . 1.378(3)
C8 N1 . 1.300(2)
C8 C9 . 1.426(3)
C9 C10 . 1.406(3)
C9 C18 . 1.449(2)
C10 O2 . 1.313(2)
C10 C11 . 1.429(3)
C11 C12 . 1.353(3)
C12 C13 . 1.420(3)
C13 C14 . 1.411(3)
C13 C18 . 1.419(3)
C14 C15 . 1.356(3)
C15 C16 . 1.400(3)
C16 C17 . 1.376(3)
C17 C18 . 1.411(3)
C19 N3 . 1.342(2)
C19 C20 . 1.369(3)
C20 C21 . 1.385(3)
C21 C23 . 1.388(3)
C21 C22 . 1.503(3)
C23 C24 . 1.366(3)
C24 N3 . 1.351(2)
N1 N2 . 1.405(2)
