#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/92/4509242.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4509242
loop_
_publ_author_name
'Siegler, Maxime A.'
'Lutz, Martin'
_publ_section_title
;
 Ni(salen): a System That Forms Many Solvates with Interacting Ni Atoms
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1194
_journal_paper_doi               10.1021/cg801109n
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         'C16 H14 N2 Ni O2, C H Cl3'
_chemical_formula_sum            'C17 H15 Cl3 N2 Ni O2'
_chemical_formula_weight         444.37
_space_group_IT_number           58
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2 2n'
_symmetry_space_group_name_H-M   'P n n m'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.2272(4)
_cell_length_b                   6.9948(3)
_cell_length_c                   18.3352(4)
_cell_measurement_reflns_used    6557
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.84
_cell_measurement_theta_min      1.81
_cell_volume                     1824.65(10)
_computing_cell_refinement       'PEAKREF (Schreurs, 2005)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'DIRDIF08 (Beurskens et al., 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0120
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30822
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    1.515
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_correction_T_min  0.485
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2006)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1669
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0614
_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)+(0.0438P)²+3.0078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1184
_reflns_number_gt                1362
_reflns_number_total             1669
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg801109nsup1.cif
_cod_data_source_block           2b
_cod_database_code               4509242
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'-x-1/2, y-1/2, z-1/2'
'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_group
Ni1 Ni 0.53356(4) 0.28221(9) 0.5000 0.0499(2) Uani 1 2 d S .
O1 O 0.62582(17) 0.3367(4) 0.56773(14) 0.0593(7) Uani 1 1 d . .
N1 N 0.4429(2) 0.2246(5) 0.5681(2) 0.0622(9) Uani 1 1 d D .
C1 C 0.6186(3) 0.3297(5) 0.6390(2) 0.0594(10) Uani 1 1 d . .
C2 C 0.5379(3) 0.2648(5) 0.6755(2) 0.0645(11) Uani 1 1 d . .
C3 C 0.5381(5) 0.2552(7) 0.7526(3) 0.0875(16) Uani 1 1 d . .
H3 H 0.4854 0.2088 0.7769 0.105 Uiso 1 1 calc R .
C4 C 0.6136(6) 0.3124(9) 0.7916(3) 0.105(2) Uani 1 1 d . .
H4 H 0.6133 0.3022 0.8422 0.126 Uiso 1 1 calc R .
C5 C 0.6910(5) 0.3859(9) 0.7561(3) 0.0987(18) Uani 1 1 d . .
H5 H 0.7416 0.4308 0.7833 0.118 Uiso 1 1 calc R .
C6 C 0.6945(3) 0.3940(7) 0.6812(2) 0.0791(13) Uani 1 1 d . .
H6 H 0.7477 0.4426 0.6583 0.095 Uiso 1 1 calc R .
C7 C 0.4540(3) 0.2184(6) 0.6379(3) 0.0705(12) Uani 1 1 d . .
H7 H 0.4027 0.1804 0.6658 0.085 Uiso 1 1 calc R .
C8 C 0.3532(5) 0.1471(15) 0.5404(5) 0.072(3) Uani 0.50 1 d PDU -1
H8A H 0.3007 0.1911 0.5697 0.086 Uiso 0.50 1 calc PR -1
H8B H 0.3539 0.0084 0.5404 0.086 Uiso 0.50 1 calc PR -1
C8' C 0.3475(5) 0.2243(16) 0.4642(6) 0.076(3) Uani 0.50 1 d PDU -1
H8'1 H 0.3059 0.1454 0.4351 0.092 Uiso 0.50 1 calc PR -1
H8'2 H 0.3226 0.3533 0.4650 0.092 Uiso 0.50 1 calc PR -1
Cl1 Cl 0.88090(15) 0.1780(4) 0.57614(9) 0.1549(9) Uani 1 1 d . .
Cl2 Cl 0.87309(14) 0.5330(4) 0.5000 0.1368(10) Uani 1 2 d S .
C9 C 0.8392(5) 0.2941(11) 0.5000 0.0808(19) Uani 1 2 d S .
H9 H 0.7704 0.2875 0.5000 0.097 Uiso 1 2 calc SR .
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'
Cl Cl 0.1484 0.1585 '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'
Ni Ni 0.3393 1.1124 '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'
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
N1 Ni1 N1 85.4(2) 6_556 .
N1 Ni1 O1 179.03(14) 6_556 .
N1 Ni1 O1 95.02(14) . .
N1 Ni1 O1 95.02(14) 6_556 6_556
N1 Ni1 O1 179.03(14) . 6_556
O1 Ni1 O1 84.53(16) . 6_556
C1 O1 Ni1 127.4(3) . .
C7 N1 C8 115.7(5) . .
C7 N1 C8' 120.6(6) . 6_556
C7 N1 Ni1 126.5(3) . .
C8 N1 Ni1 117.0(5) . .
C8' N1 Ni1 111.8(5) 6_556 .
O1 C1 C6 118.5(4) . .
O1 C1 C2 123.3(4) . .
C6 C1 C2 118.1(4) . .
C1 C2 C7 122.1(4) . .
C1 C2 C3 119.2(5) . .
C7 C2 C3 118.5(5) . .
C4 C3 C2 121.1(5) . .
C4 C3 H3 119.4 . .
C2 C3 H3 119.4 . .
C3 C4 C5 119.7(5) . .
C3 C4 H4 120.1 . .
C5 C4 H4 120.1 . .
C6 C5 C4 121.0(6) . .
C6 C5 H5 119.5 . .
C4 C5 H5 119.5 . .
C5 C6 C1 120.6(5) . .
C5 C6 H6 119.7 . .
C1 C6 H6 119.7 . .
N1 C7 C2 125.3(4) . .
N1 C7 H7 117.3 . .
C2 C7 H7 117.3 . .
N1 C8 C8' 103.5(7) . .
N1 C8 H8A 111.1 . .
C8' C8 H8A 111.1 . .
N1 C8 H8B 111.1 . .
C8' C8 H8B 111.1 . .
H8A C8 H8B 109.0 . .
N1 C8' C8 108.9(8) 6_556 .
N1 C8' H8'1 109.9 6_556 .
C8 C8' H8'1 109.9 . .
N1 C8' H8'2 109.9 6_556 .
C8 C8' H8'2 109.9 . .
H8'1 C8' H8'2 108.3 . .
Cl1 C9 Cl1 108.5(4) . 6_556
Cl1 C9 Cl2 111.0(3) . .
Cl1 C9 Cl2 111.0(3) 6_556 .
Cl1 C9 H9 108.8 . .
Cl1 C9 H9 108.8 6_556 .
Cl2 C9 H9 108.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1 1.840(3) 6_556
Ni1 N1 1.840(3) .
Ni1 O1 1.847(3) .
Ni1 O1 1.847(3) 6_556
O1 C1 1.312(4) .
N1 C7 1.291(6) .
N1 C8 1.476(6) .
N1 C8' 1.480(6) 6_556
C1 C6 1.402(6) .
C1 C2 1.405(6) .
C2 C7 1.416(6) .
C2 C3 1.416(7) .
C3 C4 1.350(8) .
C3 H3 0.9300 .
C4 C5 1.378(8) .
C4 H4 0.9300 .
C5 C6 1.376(7) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 C8' 1.501(10) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C8' N1 1.480(6) 6_556
C8' H8'1 0.9700 .
C8' H8'2 0.9700 .
Cl1 C9 1.720(4) .
Cl2 C9 1.740(8) .
C9 Cl1 1.720(4) 6_556
C9 H9 0.9800 .
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
C9 H9 O1 0.98 2.43 3.294(7) 147.1
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_4
N1 Ni1 O1 C1 0.2(3) . .
O1 Ni1 O1 C1 -179.0(3) 6_556 .
N1 Ni1 N1 C7 175.1(3) 6_556 .
O1 Ni1 N1 C7 -4.0(4) . .
N1 Ni1 N1 C8 6.0(6) 6_556 .
O1 Ni1 N1 C8 -173.2(5) . .
N1 Ni1 N1 C8' -17.0(6) 6_556 6_556
O1 Ni1 N1 C8' 163.8(5) . 6_556
Ni1 O1 C1 C6 -174.1(3) . .
Ni1 O1 C1 C2 4.5(5) . .
O1 C1 C2 C7 -6.1(6) . .
C6 C1 C2 C7 172.4(4) . .
O1 C1 C2 C3 177.5(4) . .
C6 C1 C2 C3 -4.0(6) . .
C1 C2 C3 C4 1.9(7) . .
C7 C2 C3 C4 -174.7(4) . .
C2 C3 C4 C5 1.6(8) . .
C3 C4 C5 C6 -3.0(9) . .
C4 C5 C6 C1 0.8(8) . .
O1 C1 C6 C5 -178.7(4) . .
C2 C1 C6 C5 2.7(7) . .
C8 N1 C7 C2 172.6(6) . .
C8' N1 C7 C2 -163.5(6) 6_556 .
Ni1 N1 C7 C2 3.4(6) . .
C1 C2 C7 N1 2.1(6) . .
C3 C2 C7 N1 178.5(4) . .
C7 N1 C8 C8' 163.7(6) . .
C8' N1 C8 C8' 55(2) 6_556 .
Ni1 N1 C8 C8' -25.9(9) . .
N1 C8 C8' N1 37.4(10) . 6_556
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139067410
