#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:15:59 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301787 $
#$URL: svn://www.crystallography.net/cod/cif/1/56/08/1560862.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_1560862
loop_
_publ_author_name
'Shiryaev, Alexey A.'
'Burkhanova, Tatyana M.'
'Mitoraj, Mariusz P.'
'Kukulka, Mercedes'
'Sagan, Filip'
'Mahmoudi, Ghodrat'
'Babashkina, Maria G.'
'Bolte, Michael'
'Safin, Damir A.'
_publ_section_title
;
 Supramolecular structures of NiII and CuII with the sterically demanding
 Schiff base dyes driven by cooperative action of preagostic and other
 non-covalent interactions
;
_journal_issue                   3
_journal_name_full               IUCrJ
_journal_paper_doi               10.1107/S2052252521000610
_journal_volume                  8
_journal_year                    2021
_chemical_formula_moiety         'C26 H32 Cu N2 O2'
_chemical_formula_sum            'C26 H32 Cu N2 O2'
_chemical_formula_weight         468.07
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                97.647(5)
_cell_angle_beta                 101.861(5)
_cell_angle_gamma                105.261(5)
_cell_formula_units_Z            1
_cell_length_a                   6.4641(4)
_cell_length_b                   7.7224(5)
_cell_length_c                   11.9925(7)
_cell_measurement_reflns_used    12420
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.98
_cell_measurement_theta_min      3.38
_cell_volume                     553.99(6)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12420
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.579
_diffrn_reflns_theta_min         3.375
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    1.011
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             247
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         3073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0251
_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)+(0.0362P)²+0.2633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0693
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3052
_reflns_number_total             3073
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ed5022.cif
_cod_data_source_block           ba36
_cod_database_code               1560862
_shelx_shelxl_version_number     2016/6
_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   0.765
_shelx_estimated_absorpt_t_max   0.871
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Cu1 Cu 0.500000 0.000000 0.500000 0.01445(7) Uani 1 2 d S . P . .
O1 O 0.62861(15) 0.10824(14) 0.65936(8) 0.02276(18) Uani 1 1 d . . . . .
N1 N 0.28645(16) 0.15003(13) 0.49196(8) 0.01533(17) Uani 1 1 d . . . . .
C1 C 0.52316(19) 0.15818(15) 0.73405(10) 0.0172(2) Uani 1 1 d . . . . .
C2 C 0.32425(19) 0.20477(15) 0.70143(10) 0.0165(2) Uani 1 1 d . . . . .
C3 C 0.2205(2) 0.25847(17) 0.78688(11) 0.0209(2) Uani 1 1 d . . . . .
H3 H 0.087226 0.289211 0.763784 0.025 Uiso 1 1 calc R U . . .
C4 C 0.3080(2) 0.2674(2) 0.90304(11) 0.0263(3) Uani 1 1 d . . . . .
H4 H 0.235524 0.302308 0.959692 0.032 Uiso 1 1 calc R U . . .
C5 C 0.5068(2) 0.2237(2) 0.93612(11) 0.0268(3) Uani 1 1 d . . . . .
H5 H 0.569738 0.230612 1.016079 0.032 Uiso 1 1 calc R U . . .
C6 C 0.6119(2) 0.17110(18) 0.85437(11) 0.0231(2) Uani 1 1 d . . . . .
H6 H 0.746454 0.142915 0.879114 0.028 Uiso 1 1 calc R U . . .
C7 C 0.22891(18) 0.21071(15) 0.58270(10) 0.0165(2) Uani 1 1 d . . . . .
H7 H 0.112088 0.264683 0.570066 0.020 Uiso 1 1 calc R U . . .
C11 C 0.18580(18) 0.18372(15) 0.37711(9) 0.01557(19) Uani 1 1 d . . . . .
H11 H 0.126641 0.062772 0.321933 0.019 Uiso 1 1 calc R U . . .
C12 C 0.36967(19) 0.30361(18) 0.33374(10) 0.0198(2) Uani 1 1 d . . . . .
H12A H 0.427589 0.427010 0.384201 0.024 Uiso 1 1 calc R U . . .
H12B H 0.493098 0.249291 0.338095 0.024 Uiso 1 1 calc R U . . .
C13 C 0.2817(2) 0.31991(18) 0.20825(11) 0.0214(2) Uani 1 1 d . . . . .
H13A H 0.400704 0.402576 0.182950 0.026 Uiso 1 1 calc R U . . .
H13B H 0.236701 0.197982 0.156725 0.026 Uiso 1 1 calc R U . . .
C14 C 0.0840(2) 0.39460(18) 0.19761(11) 0.0232(2) Uani 1 1 d . . . . .
H14A H 0.022288 0.394243 0.114856 0.028 Uiso 1 1 calc R U . . .
H14B H 0.133805 0.522831 0.240863 0.028 Uiso 1 1 calc R U . . .
C15 C -0.0962(2) 0.28056(19) 0.24529(11) 0.0225(2) Uani 1 1 d . . . . .
H15A H -0.157909 0.155905 0.196509 0.027 Uiso 1 1 calc R U . . .
H15B H -0.217828 0.336929 0.241562 0.027 Uiso 1 1 calc R U . . .
C16 C -0.00449(19) 0.26762(17) 0.37146(10) 0.0192(2) Uani 1 1 d . . . . .
H16A H 0.049283 0.391204 0.421615 0.023 Uiso 1 1 calc R U . . .
H16B H -0.123098 0.190565 0.399938 0.023 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'
Cu Cu 0.3201 1.2651 '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'
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 Cu1 O1 180.0 2_656 . ?
O1 Cu1 N1 89.42(4) 2_656 . ?
O1 Cu1 N1 90.58(4) . . ?
O1 Cu1 N1 90.58(4) 2_656 2_656 ?
O1 Cu1 N1 89.42(4) . 2_656 ?
N1 Cu1 N1 180.0 . 2_656 ?
C1 O1 Cu1 125.74(8) . . ?
C7 N1 C11 119.42(9) . . ?
C7 N1 Cu1 121.86(8) . . ?
C11 N1 Cu1 118.66(7) . . ?
O1 C1 C2 123.30(10) . . ?
O1 C1 C6 119.35(11) . . ?
C2 C1 C6 117.33(11) . . ?
C3 C2 C1 120.14(11) . . ?
C3 C2 C7 117.71(10) . . ?
C1 C2 C7 122.03(10) . . ?
C4 C3 C2 121.49(11) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 118.65(12) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 121.06(12) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 121.32(12) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
N1 C7 C2 126.51(10) . . ?
N1 C7 H7 116.7 . . ?
C2 C7 H7 116.7 . . ?
N1 C11 C16 116.76(9) . . ?
N1 C11 C12 108.36(9) . . ?
C16 C11 C12 109.78(9) . . ?
N1 C11 H11 107.2 . . ?
C16 C11 H11 107.2 . . ?
C12 C11 H11 107.2 . . ?
C13 C12 C11 110.60(9) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 110.78(10) . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C15 111.43(10) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 111.20(10) . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C11 C16 C15 109.20(10) . . ?
C11 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
C11 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
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
Cu1 O1 1.8969(9) 2_656 ?
Cu1 O1 1.8969(9) . ?
Cu1 N1 2.0184(9) . ?
Cu1 N1 2.0185(9) 2_656 ?
O1 C1 1.3089(14) . ?
N1 C7 1.2902(14) . ?
N1 C11 1.4846(14) . ?
C1 C2 1.4177(16) . ?
C1 C6 1.4186(16) . ?
C2 C3 1.4098(16) . ?
C2 C7 1.4424(15) . ?
C3 C4 1.3767(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3788(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C11 C16 1.5278(15) . ?
C11 C12 1.5308(16) . ?
C11 H11 1.0000 . ?
C12 C13 1.5297(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5241(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5258(17) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5341(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
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 Cu1 O1 C1 34.25(10) . . . . ?
N1 Cu1 O1 C1 -145.75(10) 2_656 . . . ?
Cu1 O1 C1 C2 -25.23(17) . . . . ?
Cu1 O1 C1 C6 156.19(9) . . . . ?
O1 C1 C2 C3 -179.60(11) . . . . ?
C6 C1 C2 C3 -1.00(17) . . . . ?
O1 C1 C2 C7 -3.64(18) . . . . ?
C6 C1 C2 C7 174.96(11) . . . . ?
C1 C2 C3 C4 0.06(19) . . . . ?
C7 C2 C3 C4 -176.07(12) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
O1 C1 C6 C5 179.79(12) . . . . ?
C2 C1 C6 C5 1.12(19) . . . . ?
C11 N1 C7 C2 -173.96(10) . . . . ?
Cu1 N1 C7 C2 8.86(16) . . . . ?
C3 C2 C7 N1 -172.55(11) . . . . ?
C1 C2 C7 N1 11.39(19) . . . . ?
C7 N1 C11 C16 -7.89(15) . . . . ?
Cu1 N1 C11 C16 169.38(8) . . . . ?
C7 N1 C11 C12 116.64(11) . . . . ?
Cu1 N1 C11 C12 -66.09(10) . . . . ?
N1 C11 C12 C13 171.81(9) . . . . ?
C16 C11 C12 C13 -59.61(13) . . . . ?
C11 C12 C13 C14 56.44(14) . . . . ?
C12 C13 C14 C15 -54.34(14) . . . . ?
C13 C14 C15 C16 55.61(15) . . . . ?
N1 C11 C16 C15 -176.38(10) . . . . ?
C12 C11 C16 C15 59.83(12) . . . . ?
C14 C15 C16 C11 -58.06(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 154702779
