#------------------------------------------------------------------------------
#$Date: 2020-12-31 02:19:04 +0200 (Thu, 31 Dec 2020) $
#$Revision: 260274 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/98/1559886.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_1559886
loop_
_publ_author_name
'Collett, Joel D.'
'Krause, Jeanette A.'
'Guan, Hairong'
_publ_section_title
;
 Multiweek Experiments for an Inorganic Chemistry Laboratory Course:
 Synthesis of Nickel Complexes Supported by a Tetradentate Ligand with a
 N2O2 Donor Set
;
_journal_name_full               'Journal of Chemical Education'
_journal_paper_doi               10.1021/acs.jchemed.0c01117
_journal_year                    2020
_chemical_formula_moiety         'C44 H44 N4 O8 Ni2, 2(C2 H3 N)'
_chemical_formula_sum            'C48 H50 N6 Ni2 O8'
_chemical_formula_weight         956.36
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 91.4245(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.8061(5)
_cell_length_b                   10.1122(4)
_cell_length_c                   15.8955(6)
_cell_measurement_reflns_used    9753
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.39
_cell_volume                     2218.49(15)
_computing_cell_refinement       'Bruker SAINT v8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker APEX3 v2019.2-37 (Bruker, 2019)'
_computing_data_reduction        'Bruker SAINT v8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  'Bruker SHELXTL v6.14'
_computing_structure_refinement
'SHELXL-2017/1 (Sheldrick, 2018, G.M. Sheldrick (2015) Acta Cryst., C71, 3-8)'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture Photon-II'
_diffrn_measurement_method       'ω-φ scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            75810
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.313
_diffrn_reflns_theta_min         2.497
_diffrn_source                   'Incoatec Mo-microfocus 3.0'
_exptl_absorpt_coefficient_mu    0.911
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS 2016/2 (L.Krause, et al. J. Appl. Cryst. (2015), 48, 3-10)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       rod
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         5511
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0320
_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)+(0.0154P)²+2.1278P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0679
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4695
_reflns_number_total             5511
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ed0c01117_si_011.cif
_cod_data_source_block           Ni(salophen)(HOAc)-dimer
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1559886
_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   0.887
_shelx_estimated_absorpt_t_max   0.982
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_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
Ni Ni 0.48915(2) 0.35587(2) 0.52945(2) 0.01498(6) Uani 1 1 d . . . . .
O1 O 0.59656(8) 0.48109(11) 0.49230(7) 0.0169(2) Uani 1 1 d . . . . .
O2 O 0.38026(9) 0.22514(12) 0.56706(7) 0.0191(2) Uani 1 1 d . . . . .
H3 H 0.3881(14) 0.161(2) 0.5301(13) 0.023 Uiso 1 1 d . U . . .
O3 O 0.46554(9) 0.28866(11) 0.40713(7) 0.0195(2) Uani 1 1 d . . . . .
O4 O 0.41061(10) 0.08801(12) 0.44050(8) 0.0251(3) Uani 1 1 d . . . . .
N1 N 0.59162(10) 0.21305(14) 0.56282(9) 0.0172(3) Uani 1 1 d . . . . .
H1 H 0.5695(14) 0.131(2) 0.5604(12) 0.021 Uiso 1 1 d . U . . .
N2 N 0.50837(10) 0.41678(14) 0.65301(9) 0.0172(3) Uani 1 1 d . . . . .
H2 H 0.5233(14) 0.498(2) 0.6488(12) 0.021 Uiso 1 1 d . U . . .
C1 C 0.69158(11) 0.46704(16) 0.51074(10) 0.0164(3) Uani 1 1 d . . . . .
C2 C 0.75221(12) 0.57593(17) 0.52567(10) 0.0198(3) Uani 1 1 d . . . . .
H2A H 0.725700 0.662578 0.523186 0.024 Uiso 1 1 calc R U . . .
C3 C 0.85026(12) 0.55975(18) 0.54404(11) 0.0236(4) Uani 1 1 d . . . . .
H3A H 0.889804 0.635400 0.553641 0.028 Uiso 1 1 calc R U . . .
C4 C 0.89138(13) 0.43473(19) 0.54859(12) 0.0258(4) Uani 1 1 d . . . . .
H4A H 0.958575 0.423961 0.561023 0.031 Uiso 1 1 calc R U . . .
C5 C 0.83210(13) 0.32579(18) 0.53456(11) 0.0232(4) Uani 1 1 d . . . . .
H5A H 0.859307 0.239617 0.538127 0.028 Uiso 1 1 calc R U . . .
C6 C 0.73366(12) 0.33973(16) 0.51538(10) 0.0178(3) Uani 1 1 d . . . . .
C7 C 0.67270(12) 0.21875(16) 0.50189(11) 0.0196(3) Uani 1 1 d . . . . .
H7A H 0.713740 0.139019 0.508815 0.024 Uiso 1 1 calc R U . . .
H7B H 0.645454 0.218955 0.443688 0.024 Uiso 1 1 calc R U . . .
C8 C 0.62583(12) 0.23679(16) 0.64889(10) 0.0176(3) Uani 1 1 d . . . . .
C9 C 0.69780(12) 0.15874(17) 0.68658(11) 0.0219(3) Uani 1 1 d . . . . .
H9A H 0.723697 0.085654 0.657064 0.026 Uiso 1 1 calc R U . . .
C10 C 0.73149(13) 0.18804(19) 0.76721(11) 0.0262(4) Uani 1 1 d . . . . .
H10A H 0.779678 0.133812 0.793378 0.031 Uiso 1 1 calc R U . . .
C11 C 0.69525(13) 0.29617(19) 0.81003(11) 0.0266(4) Uani 1 1 d . . . . .
H11A H 0.720002 0.317267 0.864690 0.032 Uiso 1 1 calc R U . . .
C12 C 0.62292(13) 0.37346(18) 0.77308(11) 0.0223(4) Uani 1 1 d . . . . .
H12A H 0.597600 0.446932 0.802601 0.027 Uiso 1 1 calc R U . . .
C13 C 0.58744(12) 0.34304(16) 0.69244(10) 0.0177(3) Uani 1 1 d . . . . .
C14 C 0.41652(12) 0.40735(17) 0.70028(11) 0.0208(3) Uani 1 1 d . . . . .
H14A H 0.364682 0.455057 0.668643 0.025 Uiso 1 1 calc R U . . .
H14B H 0.425714 0.451528 0.755484 0.025 Uiso 1 1 calc R U . . .
C15 C 0.38467(12) 0.26665(17) 0.71438(11) 0.0199(3) Uani 1 1 d . . . . .
C16 C 0.36980(14) 0.21962(19) 0.79542(11) 0.0266(4) Uani 1 1 d . . . . .
H16A H 0.382396 0.276352 0.842054 0.032 Uiso 1 1 calc R U . . .
C17 C 0.33695(14) 0.0916(2) 0.80984(12) 0.0299(4) Uani 1 1 d . . . . .
H17A H 0.327381 0.061491 0.865630 0.036 Uiso 1 1 calc R U . . .
C18 C 0.31833(13) 0.00858(19) 0.74192(12) 0.0265(4) Uani 1 1 d . . . . .
H18A H 0.294925 -0.078441 0.751115 0.032 Uiso 1 1 calc R U . . .
C19 C 0.33377(12) 0.05209(17) 0.66068(11) 0.0220(4) Uani 1 1 d . . . . .
H19A H 0.321579 -0.005425 0.614363 0.026 Uiso 1 1 calc R U . . .
C20 C 0.36706(12) 0.17981(16) 0.64688(10) 0.0180(3) Uani 1 1 d . . . . .
C21 C 0.44142(12) 0.17180(16) 0.38803(10) 0.0187(3) Uani 1 1 d . . . . .
C22 C 0.44948(14) 0.12977(19) 0.29745(11) 0.0262(4) Uani 1 1 d . . . . .
H22A H 0.497705 0.184903 0.269901 0.039 Uiso 1 1 calc R U . . .
H22B H 0.386479 0.140213 0.268432 0.039 Uiso 1 1 calc R U . . .
H22C H 0.469480 0.036883 0.295143 0.039 Uiso 1 1 calc R U . . .
N3 N 0.63020(19) 0.4660(2) 0.98952(17) 0.0652(7) Uani 1 1 d . . . . .
C23 C 0.61535(18) 0.3987(2) 1.04519(17) 0.0465(6) Uani 1 1 d . . . . .
C24 C 0.5974(2) 0.3120(3) 1.11569(16) 0.0534(7) Uani 1 1 d . . . . .
H24A H 0.615652 0.221332 1.101117 0.080 Uiso 1 1 calc R U . . .
H24B H 0.528408 0.314656 1.128778 0.080 Uiso 1 1 calc R U . . .
H24C H 0.635899 0.341271 1.164841 0.080 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 Ni O1 82.73(5) . 3_666 ?
O1 Ni N2 90.74(5) . . ?
O1 Ni N2 88.89(5) 3_666 . ?
O1 Ni O3 91.73(4) . . ?
O1 Ni O3 91.64(5) 3_666 . ?
N2 Ni O3 177.51(5) . . ?
O1 Ni N1 90.58(5) . . ?
O1 Ni N1 170.13(5) 3_666 . ?
N2 Ni N1 83.94(5) . . ?
O3 Ni N1 95.82(5) . . ?
O1 Ni O2 179.17(5) . . ?
O1 Ni O2 98.03(5) 3_666 . ?
N2 Ni O2 89.60(5) . . ?
O3 Ni O2 87.92(5) . . ?
N1 Ni O2 88.71(5) . . ?
C1 O1 Ni 125.54(10) . . ?
C1 O1 Ni 132.57(10) . 3_666 ?
Ni O1 Ni 97.27(5) . 3_666 ?
C20 O2 Ni 126.08(10) . . ?
C21 O3 Ni 124.43(11) . . ?
C8 N1 C7 111.75(13) . . ?
C8 N1 Ni 109.12(10) . . ?
C7 N1 Ni 108.80(10) . . ?
C13 N2 C14 112.88(13) . . ?
C13 N2 Ni 109.53(10) . . ?
C14 N2 Ni 111.61(10) . . ?
O1 C1 C2 122.00(15) . . ?
O1 C1 C6 120.34(14) . . ?
C2 C1 C6 117.66(15) . . ?
C3 C2 C1 121.27(16) . . ?
C4 C3 C2 120.96(17) . . ?
C3 C4 C5 118.45(16) . . ?
C4 C5 C6 121.57(16) . . ?
C5 C6 C1 120.08(15) . . ?
C5 C6 C7 119.39(15) . . ?
C1 C6 C7 120.51(14) . . ?
C6 C7 N1 111.40(13) . . ?
C13 C8 C9 120.03(15) . . ?
C13 C8 N1 118.46(14) . . ?
C9 C8 N1 121.47(15) . . ?
C10 C9 C8 119.78(17) . . ?
C9 C10 C11 120.37(17) . . ?
C12 C11 C10 120.06(17) . . ?
C11 C12 C13 119.83(17) . . ?
C8 C13 C12 119.90(15) . . ?
C8 C13 N2 118.29(14) . . ?
C12 C13 N2 121.77(15) . . ?
N2 C14 C15 112.94(13) . . ?
C16 C15 C20 117.82(16) . . ?
C16 C15 C14 120.66(16) . . ?
C20 C15 C14 121.51(15) . . ?
C17 C16 C15 121.72(17) . . ?
C18 C17 C16 119.31(17) . . ?
C19 C18 C17 120.23(17) . . ?
C18 C19 C20 120.08(17) . . ?
O2 C20 C19 120.71(15) . . ?
O2 C20 C15 118.42(15) . . ?
C19 C20 C15 120.83(15) . . ?
O3 C21 O4 123.86(15) . . ?
O3 C21 C22 117.91(15) . . ?
O4 C21 C22 118.23(15) . . ?
N3 C23 C24 179.3(3) . . ?
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 O1 2.0481(11) . ?
Ni O1 2.0536(11) 3_666 ?
Ni N2 2.0690(14) . ?
Ni O3 2.0779(11) . ?
Ni N1 2.0811(14) . ?
Ni O2 2.1000(12) . ?
O1 C1 1.3446(19) . ?
O2 C20 1.3655(19) . ?
O3 C21 1.263(2) . ?
O4 C21 1.270(2) . ?
N1 C8 1.456(2) . ?
N1 C7 1.499(2) . ?
N2 C13 1.451(2) . ?
N2 C14 1.493(2) . ?
C1 C2 1.400(2) . ?
C1 C6 1.414(2) . ?
C2 C3 1.387(2) . ?
C3 C4 1.387(3) . ?
C4 C5 1.387(3) . ?
C5 C6 1.393(2) . ?
C6 C7 1.497(2) . ?
C8 C13 1.390(2) . ?
C8 C9 1.393(2) . ?
C9 C10 1.385(3) . ?
C10 C11 1.388(3) . ?
C11 C12 1.387(3) . ?
C12 C13 1.395(2) . ?
C14 C15 1.508(2) . ?
C15 C16 1.393(2) . ?
C15 C20 1.403(2) . ?
C16 C17 1.392(3) . ?
C17 C18 1.387(3) . ?
C18 C19 1.386(2) . ?
C19 C20 1.390(2) . ?
C21 C22 1.508(2) . ?
N3 C23 1.139(3) . ?
C23 C24 1.450(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
N1 H1 O4 0.88(2) 2.24(2) 3.0449(19) 152.6(17) 3_656 yes
N2 H2 O3 0.85(2) 2.34(2) 3.1516(18) 159.9(18) 3_666 yes
O2 H3 O4 0.89(2) 1.64(2) 2.4876(17) 159.3(19) . yes
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
Ni O1 C1 C2 -144.75(13) . . . . ?
Ni O1 C1 C2 5.4(2) 3_666 . . . ?
Ni O1 C1 C6 35.4(2) . . . . ?
Ni O1 C1 C6 -174.40(11) 3_666 . . . ?
O1 C1 C2 C3 -179.54(15) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C4 C5 C6 C7 -179.23(16) . . . . ?
O1 C1 C6 C5 -179.96(14) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
O1 C1 C6 C7 -1.5(2) . . . . ?
C2 C1 C6 C7 178.72(15) . . . . ?
C5 C6 C7 N1 120.84(16) . . . . ?
C1 C6 C7 N1 -57.7(2) . . . . ?
C8 N1 C7 C6 -48.53(18) . . . . ?
Ni N1 C7 C6 72.02(14) . . . . ?
C7 N1 C8 C13 120.57(16) . . . . ?
Ni N1 C8 C13 0.19(17) . . . . ?
C7 N1 C8 C9 -57.1(2) . . . . ?
Ni N1 C8 C9 -177.51(13) . . . . ?
C13 C8 C9 C10 -0.5(3) . . . . ?
N1 C8 C9 C10 177.12(15) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C10 C11 C12 1.8(3) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C9 C8 C13 C12 1.7(2) . . . . ?
N1 C8 C13 C12 -176.04(15) . . . . ?
C9 C8 C13 N2 -176.19(15) . . . . ?
N1 C8 C13 N2 6.1(2) . . . . ?
C11 C12 C13 C8 -1.1(3) . . . . ?
C11 C12 C13 N2 176.72(15) . . . . ?
C14 N2 C13 C8 116.03(16) . . . . ?
Ni N2 C13 C8 -8.99(17) . . . . ?
C14 N2 C13 C12 -61.8(2) . . . . ?
Ni N2 C13 C12 173.17(13) . . . . ?
C13 N2 C14 C15 -55.42(18) . . . . ?
Ni N2 C14 C15 68.46(15) . . . . ?
N2 C14 C15 C16 123.31(17) . . . . ?
N2 C14 C15 C20 -58.1(2) . . . . ?
C20 C15 C16 C17 -1.1(3) . . . . ?
C14 C15 C16 C17 177.59(17) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
Ni O2 C20 C19 -145.25(13) . . . . ?
Ni O2 C20 C15 36.9(2) . . . . ?
C18 C19 C20 O2 -178.34(15) . . . . ?
C18 C19 C20 C15 -0.6(3) . . . . ?
C16 C15 C20 O2 179.24(15) . . . . ?
C14 C15 C20 O2 0.6(2) . . . . ?
C16 C15 C20 C19 1.4(2) . . . . ?
C14 C15 C20 C19 -177.25(15) . . . . ?
Ni O3 C21 O4 14.1(2) . . . . ?
Ni O3 C21 C22 -166.07(11) . . . . ?
