#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:18:24 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257994 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/07/7240783.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_7240783
loop_
_publ_author_name
'Nasibipour, Mina'
'Safaei, Elham'
'Masoumpour, Marziyeh Sadat'
'Wojtczak, Andrzej'
_publ_section_title
;
 Ancillary ligand electro-activity effects towards phenyl acetylene
 homocoupling reaction by a nickel(ii) complex of a non-innocent O-amino
 phenol ligand: a mechanistic insight
;
_journal_issue                   41
_journal_name_full               'RSC Advances'
_journal_page_first              24176
_journal_page_last               24189
_journal_paper_doi               10.1039/D0RA04362A
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C42 H48 N4 Ni O2'
_chemical_formula_sum            'C42 H48 N4 Ni O2'
_chemical_formula_weight         699.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-12-28 deposited with the CCDC.	2020-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.733(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.469(2)
_cell_length_b                   8.1558(8)
_cell_length_c                   16.897(2)
_cell_measurement_reflns_used    6912
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0860
_cell_measurement_theta_min      2.4690
_cell_volume                     1990.1(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_publication_material  'CIFTAB-2017 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXS-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.2564
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13001
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.446
_diffrn_reflns_theta_min         2.412
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.529
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0462
_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)+(0.0569P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1146
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3204
_reflns_number_total             4554
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra04362a2.cif
_cod_data_source_block           e1365a
_cod_depositor_comments          'Adding full bibliography for 7240783.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7240783
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.769
_shelx_estimated_absorpt_t_max   0.939
_exptl_absorpt_special_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.000000 0.500000 0.000000 0.03184(13) Uani 1 2 d S . P . .
O1 O 0.11502(9) 0.40417(18) 0.05706(9) 0.0381(4) Uani 1 1 d . . . . .
C1 C 0.17645(13) 0.4750(2) 0.03948(13) 0.0325(5) Uani 1 1 d . . . . .
C2 C 0.26977(14) 0.4210(3) 0.07470(13) 0.0358(5) Uani 1 1 d . . . . .
C3 C 0.32289(15) 0.5101(3) 0.04716(15) 0.0413(5) Uani 1 1 d . . . . .
H3A H 0.383846 0.476681 0.068253 0.050 Uiso 1 1 calc R U . . .
C4 C 0.29194(14) 0.6494(3) -0.01111(14) 0.0398(5) Uani 1 1 d . . . . .
C5 C 0.20231(13) 0.6991(3) -0.04472(14) 0.0375(5) Uani 1 1 d . . . . .
H5A H 0.180293 0.789002 -0.083159 0.045 Uiso 1 1 calc R U . . .
C6 C 0.14302(13) 0.6119(2) -0.02038(13) 0.0316(4) Uani 1 1 d . . . . .
N1 N 0.05221(11) 0.6408(2) -0.04902(10) 0.0327(4) Uani 1 1 d . . . . .
C7 C 0.00601(13) 0.7737(2) -0.10836(13) 0.0309(4) Uani 1 1 d . . . . .
C8 C 0.02623(15) 0.9354(3) -0.08028(15) 0.0410(5) Uani 1 1 d . . . . .
H8A H 0.073043 0.958731 -0.022267 0.049 Uiso 1 1 calc R U . . .
C9 C -0.02270(18) 1.0623(3) -0.13792(18) 0.0514(6) Uani 1 1 d . . . . .
H9A H -0.008699 1.170347 -0.118392 0.062 Uiso 1 1 calc R U . . .
C10 C -0.09225(19) 1.0293(3) -0.22432(18) 0.0520(6) Uani 1 1 d . . . . .
H10A H -0.125411 1.114788 -0.262765 0.062 Uiso 1 1 calc R U . . .
C11 C -0.11214(15) 0.8702(3) -0.25308(15) 0.0454(6) Uani 1 1 d . . . . .
H11A H -0.158324 0.848273 -0.311589 0.054 Uiso 1 1 calc R U . . .
C12 C -0.06403(14) 0.7406(2) -0.19575(13) 0.0333(4) Uani 1 1 d . . . . .
C13 C -0.08496(15) 0.5729(3) -0.22554(14) 0.0395(5) Uani 1 1 d . . . . .
N2 N -0.10161(16) 0.4404(3) -0.24924(15) 0.0599(6) Uani 1 1 d . . . . .
C14 C 0.30808(14) 0.2773(3) 0.14142(15) 0.0433(5) Uani 1 1 d . . . . .
C15 C 0.40716(17) 0.2318(3) 0.16248(19) 0.0634(7) Uani 1 1 d . . . . .
H15A H 0.407020 0.198435 0.107932 0.076 Uiso 1 1 calc R U . . .
H15B H 0.446908 0.325225 0.187451 0.076 Uiso 1 1 calc R U . . .
H15C H 0.429365 0.143332 0.205210 0.076 Uiso 1 1 calc R U . . .
C16 C 0.31074(17) 0.3297(4) 0.22941(16) 0.0632(7) Uani 1 1 d . . . . .
H16A H 0.348749 0.425599 0.252609 0.076 Uiso 1 1 calc R U . . .
H16B H 0.249074 0.353856 0.218231 0.076 Uiso 1 1 calc R U . . .
H16C H 0.336082 0.242479 0.272715 0.076 Uiso 1 1 calc R U . . .
C17 C 0.24748(18) 0.1244(3) 0.1047(2) 0.0645(7) Uani 1 1 d . . . . .
H17A H 0.245700 0.091285 0.049343 0.077 Uiso 1 1 calc R U . . .
H17B H 0.272850 0.037366 0.148041 0.077 Uiso 1 1 calc R U . . .
H17C H 0.185841 0.148743 0.093557 0.077 Uiso 1 1 calc R U . . .
C18 C 0.36061(15) 0.7340(3) -0.03471(17) 0.0516(6) Uani 1 1 d . . . . .
C19 C 0.32378(19) 0.8957(4) -0.0836(2) 0.0854(11) Uani 1 1 d . . . . .
H19A H 0.311237 0.968341 -0.046052 0.103 Uiso 1 1 calc R U . . .
H19B H 0.369073 0.944489 -0.096620 0.103 Uiso 1 1 calc R U . . .
H19C H 0.267730 0.876419 -0.138939 0.103 Uiso 1 1 calc R U . . .
C20 C 0.45073(18) 0.7724(4) 0.0521(2) 0.0798(9) Uani 1 1 d . . . . .
H20A H 0.476223 0.672745 0.084981 0.096 Uiso 1 1 calc R U . . .
H20B H 0.494375 0.821553 0.036845 0.096 Uiso 1 1 calc R U . . .
H20C H 0.437911 0.846910 0.088680 0.096 Uiso 1 1 calc R U . . .
C21 C 0.3808(2) 0.6175(5) -0.0941(2) 0.0952(11) Uani 1 1 d . . . . .
H21A H 0.404038 0.515548 -0.062904 0.114 Uiso 1 1 calc R U . . .
H21B H 0.324809 0.597866 -0.149464 0.114 Uiso 1 1 calc R U . . .
H21C H 0.426152 0.665936 -0.107145 0.114 Uiso 1 1 calc R U . . .
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
_geom_angle_publ_flag
O1 Ni1 O1 180.0 . 3_565 ?
O1 Ni1 N1 85.13(6) . . ?
O1 Ni1 N1 94.87(6) 3_565 . ?
O1 Ni1 N1 94.87(6) . 3_565 ?
O1 Ni1 N1 85.13(6) 3_565 3_565 ?
N1 Ni1 N1 180.0 . 3_565 ?
C1 O1 Ni1 113.91(12) . . ?
O1 C1 C2 124.18(18) . . ?
O1 C1 C6 115.24(17) . . ?
C2 C1 C6 120.57(17) . . ?
C3 C2 C1 115.37(19) . . ?
C3 C2 C14 123.12(19) . . ?
C1 C2 C14 121.48(18) . . ?
C2 C3 C4 125.31(19) . . ?
C2 C3 H3A 117.3 . . ?
C4 C3 H3A 117.3 . . ?
C5 C4 C3 118.67(18) . . ?
C5 C4 C18 123.0(2) . . ?
C3 C4 C18 118.33(19) . . ?
C4 C5 C6 119.24(19) . . ?
C4 C5 H5A 120.4 . . ?
C6 C5 H5A 120.4 . . ?
N1 C6 C5 127.28(18) . . ?
N1 C6 C1 111.90(16) . . ?
C5 C6 C1 120.82(18) . . ?
C6 N1 C7 120.60(16) . . ?
C6 N1 Ni1 113.79(13) . . ?
C7 N1 Ni1 125.55(13) . . ?
C8 C7 C12 119.10(18) . . ?
C8 C7 N1 121.61(18) . . ?
C12 C7 N1 119.24(17) . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
C10 C11 C12 120.8(2) . . ?
C10 C11 H11A 119.6 . . ?
C12 C11 H11A 119.6 . . ?
C7 C12 C11 119.54(19) . . ?
C7 C12 C13 119.38(18) . . ?
C11 C12 C13 121.08(19) . . ?
N2 C13 C12 179.9(4) . . ?
C16 C14 C17 109.3(2) . . ?
C16 C14 C2 108.09(19) . . ?
C17 C14 C2 111.49(19) . . ?
C16 C14 C15 108.14(19) . . ?
C17 C14 C15 108.0(2) . . ?
C2 C14 C15 111.69(18) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C21 109.8(2) . . ?
C19 C18 C4 112.37(19) . . ?
C21 C18 C4 108.1(2) . . ?
C19 C18 C20 107.0(2) . . ?
C21 C18 C20 109.8(2) . . ?
C4 C18 C20 109.8(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
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
Ni1 O1 1.8365(13) . ?
Ni1 O1 1.8366(13) 3_565 ?
Ni1 N1 1.8516(15) . ?
Ni1 N1 1.8516(15) 3_565 ?
O1 C1 1.317(2) . ?
C1 C2 1.425(3) . ?
C1 C6 1.428(3) . ?
C2 C3 1.379(3) . ?
C2 C14 1.536(3) . ?
C3 C4 1.427(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.364(3) . ?
C4 C18 1.532(3) . ?
C5 C6 1.419(3) . ?
C5 H5A 0.9300 . ?
C6 N1 1.353(2) . ?
N1 C7 1.423(2) . ?
C7 C8 1.387(3) . ?
C7 C12 1.395(3) . ?
C8 C9 1.384(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.381(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.369(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.395(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.441(3) . ?
C13 N2 1.139(3) . ?
C14 C16 1.527(3) . ?
C14 C17 1.530(3) . ?
C14 C15 1.539(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.519(4) . ?
C18 C21 1.530(4) . ?
C18 C20 1.536(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Ni1 O1 C1 0.92(14) . . . . ?
N1 Ni1 O1 C1 -179.08(14) 3_565 . . . ?
Ni1 O1 C1 C2 -178.96(15) . . . . ?
Ni1 O1 C1 C6 -0.2(2) . . . . ?
O1 C1 C2 C3 179.02(19) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
O1 C1 C2 C14 -3.1(3) . . . . ?
C6 C1 C2 C14 178.12(19) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C14 C2 C3 C4 -176.8(2) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C2 C3 C4 C18 179.9(2) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C18 C4 C5 C6 179.0(2) . . . . ?
C4 C5 C6 N1 -178.0(2) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
O1 C1 C6 N1 -1.1(3) . . . . ?
C2 C1 C6 N1 177.79(17) . . . . ?
O1 C1 C6 C5 179.97(17) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
C5 C6 N1 C7 -1.9(3) . . . . ?
C1 C6 N1 C7 179.18(16) . . . . ?
C5 C6 N1 Ni1 -179.34(16) . . . . ?
C1 C6 N1 Ni1 1.8(2) . . . . ?
O1 Ni1 N1 C6 -1.52(14) . . . . ?
O1 Ni1 N1 C6 178.47(14) 3_565 . . . ?
O1 Ni1 N1 C7 -178.79(16) . . . . ?
O1 Ni1 N1 C7 1.21(16) 3_565 . . . ?
C6 N1 C7 C8 -68.7(2) . . . . ?
Ni1 N1 C7 C8 108.40(19) . . . . ?
C6 N1 C7 C12 114.0(2) . . . . ?
Ni1 N1 C7 C12 -68.9(2) . . . . ?
C12 C7 C8 C9 0.4(3) . . . . ?
N1 C7 C8 C9 -176.91(19) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
N1 C7 C12 C11 177.43(18) . . . . ?
C8 C7 C12 C13 179.59(18) . . . . ?
N1 C7 C12 C13 -3.1(3) . . . . ?
C10 C11 C12 C7 -0.8(3) . . . . ?
C10 C11 C12 C13 179.7(2) . . . . ?
C3 C2 C14 C16 111.0(2) . . . . ?
C1 C2 C14 C16 -66.6(3) . . . . ?
C3 C2 C14 C17 -128.8(2) . . . . ?
C1 C2 C14 C17 53.5(3) . . . . ?
C3 C2 C14 C15 -7.8(3) . . . . ?
C1 C2 C14 C15 174.5(2) . . . . ?
C5 C4 C18 C19 11.2(3) . . . . ?
C3 C4 C18 C19 -170.3(2) . . . . ?
C5 C4 C18 C21 -110.2(3) . . . . ?
C3 C4 C18 C21 68.4(3) . . . . ?
C5 C4 C18 C20 130.1(2) . . . . ?
C3 C4 C18 C20 -51.3(3) . . . . ?
