#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:15:59 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301787 $
#$URL: svn://www.crystallography.net/cod/cif/1/56/08/1560864.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_1560864
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         'C34 H36 Cu N2 O2'
_chemical_formula_sum            'C34 H36 Cu N2 O2'
_chemical_formula_weight         568.19
_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
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 99.410(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0325(10)
_cell_length_b                   5.6889(3)
_cell_length_c                   21.554(2)
_cell_measurement_reflns_used    14124
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.98
_cell_measurement_theta_min      3.67
_cell_volume                     1334.59(19)
_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_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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  0.0317
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10452
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.588
_diffrn_reflns_theta_min         3.678
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            'green yellow'
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       needle
_exptl_crystal_F_000             598
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0373
_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)+(0.0357P)²+1.0752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0842
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2186
_reflns_number_total             2485
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ed5022.cif
_cod_data_source_block           ba41
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1560864
_shelx_shelxl_version_number     2018/3
_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   0.890
_shelx_estimated_absorpt_t_max   0.975
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
Cu1 Cu 0.500000 0.500000 0.000000 0.01558(12) Uani 1 2 d S . P . .
N1 N 0.41290(17) 0.4602(3) 0.07499(8) 0.0159(4) Uani 1 1 d . . . . .
O1 O 0.58807(15) 0.2180(3) 0.02154(7) 0.0214(4) Uani 1 1 d . . . . .
C1 C 0.5975(2) 0.0860(4) 0.07113(10) 0.0170(4) Uani 1 1 d . . . . .
C2 C 0.6759(2) -0.1170(4) 0.07234(10) 0.0193(5) Uani 1 1 d . . . . .
H2 H 0.718329 -0.144689 0.038089 0.023 Uiso 1 1 calc R U . . .
C3 C 0.6903(2) -0.2691(4) 0.12128(10) 0.0190(5) Uani 1 1 d . . . . .
H3 H 0.740333 -0.404370 0.120014 0.023 Uiso 1 1 calc R U . . .
C4 C 0.6319(2) -0.2305(4) 0.17460(10) 0.0175(5) Uani 1 1 d . . . . .
C5 C 0.6493(2) -0.3908(4) 0.22552(10) 0.0212(5) Uani 1 1 d . . . . .
H5 H 0.698762 -0.526297 0.223466 0.025 Uiso 1 1 calc R U . . .
C6 C 0.5957(2) -0.3534(4) 0.27782(11) 0.0257(5) Uani 1 1 d . . . . .
H6 H 0.606347 -0.463609 0.311374 0.031 Uiso 1 1 calc R U . . .
C7 C 0.5253(2) -0.1514(4) 0.28107(11) 0.0268(5) Uani 1 1 d . . . . .
H7 H 0.489679 -0.122793 0.317610 0.032 Uiso 1 1 calc R U . . .
C8 C 0.5066(2) 0.0077(5) 0.23201(10) 0.0235(5) Uani 1 1 d . . . . .
H8 H 0.458901 0.144505 0.235631 0.028 Uiso 1 1 calc R U . . .
C9 C 0.55700(19) -0.0289(4) 0.17647(10) 0.0169(4) Uani 1 1 d . . . . .
C10 C 0.5359(2) 0.1262(4) 0.12215(10) 0.0168(4) Uani 1 1 d . . . . .
C11 C 0.4448(2) 0.3090(4) 0.11920(10) 0.0165(4) Uani 1 1 d . . . . .
H11 H 0.402910 0.319525 0.154264 0.020 Uiso 1 1 calc R U . . .
C21 C 0.3120(2) 0.6264(4) 0.08202(10) 0.0181(5) Uani 1 1 d . . . . .
H21 H 0.341274 0.787134 0.072876 0.022 Uiso 1 1 calc R U . . .
C22 C 0.2713(2) 0.6386(4) 0.14648(11) 0.0250(5) Uani 1 1 d . . . . .
H22A H 0.343287 0.667974 0.179509 0.030 Uiso 1 1 calc R U . . .
H22B H 0.233598 0.487527 0.155834 0.030 Uiso 1 1 calc R U . . .
C23 C 0.1779(3) 0.8382(5) 0.14579(13) 0.0356(7) Uani 1 1 d . . . . .
H23A H 0.150456 0.846133 0.187223 0.043 Uiso 1 1 calc R U . . .
H23B H 0.217961 0.989461 0.138785 0.043 Uiso 1 1 calc R U . . .
C24 C 0.0667(3) 0.8032(6) 0.09463(14) 0.0395(7) Uani 1 1 d . . . . .
H24A H 0.019906 0.663996 0.104880 0.047 Uiso 1 1 calc R U . . .
H24B H 0.012226 0.942033 0.093257 0.047 Uiso 1 1 calc R U . . .
C25 C 0.1045(2) 0.7689(5) 0.03056(13) 0.0294(6) Uani 1 1 d . . . . .
H25A H 0.138871 0.917730 0.017153 0.035 Uiso 1 1 calc R U . . .
H25B H 0.031085 0.728971 -0.000593 0.035 Uiso 1 1 calc R U . . .
C26 C 0.2001(2) 0.5735(4) 0.03187(12) 0.0238(5) Uani 1 1 d . . . . .
H26A H 0.225971 0.561069 -0.009861 0.029 Uiso 1 1 calc R U . . .
H26B H 0.163447 0.421410 0.041280 0.029 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 . 3_665 ?
O1 Cu1 N1 89.94(7) . 3_665 ?
O1 Cu1 N1 90.06(7) 3_665 3_665 ?
O1 Cu1 N1 90.06(7) . . ?
O1 Cu1 N1 89.94(7) 3_665 . ?
N1 Cu1 N1 180.0 3_665 . ?
C11 N1 C21 117.86(18) . . ?
C11 N1 Cu1 123.86(15) . . ?
C21 N1 Cu1 118.12(13) . . ?
C1 O1 Cu1 131.44(15) . . ?
O1 C1 C10 124.6(2) . . ?
O1 C1 C2 116.53(19) . . ?
C10 C1 C2 118.9(2) . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C9 120.3(2) . . ?
C5 C4 C3 120.3(2) . . ?
C9 C4 C3 119.4(2) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 121.4(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C4 117.0(2) . . ?
C8 C9 C10 124.0(2) . . ?
C4 C9 C10 119.01(19) . . ?
C1 C10 C11 120.46(19) . . ?
C1 C10 C9 119.9(2) . . ?
C11 C10 C9 119.49(19) . . ?
N1 C11 C10 128.2(2) . . ?
N1 C11 H11 115.9 . . ?
C10 C11 H11 115.9 . . ?
N1 C21 C22 117.18(18) . . ?
N1 C21 C26 109.50(18) . . ?
C22 C21 C26 109.12(19) . . ?
N1 C21 H21 106.8 . . ?
C22 C21 H21 106.8 . . ?
C26 C21 H21 106.8 . . ?
C21 C22 C23 108.75(19) . . ?
C21 C22 H22A 109.9 . . ?
C23 C22 H22A 109.9 . . ?
C21 C22 H22B 109.9 . . ?
C23 C22 H22B 109.9 . . ?
H22A C22 H22B 108.3 . . ?
C24 C23 C22 111.8(2) . . ?
C24 C23 H23A 109.3 . . ?
C22 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 107.9 . . ?
C25 C24 C23 111.5(2) . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
C23 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 C26 111.5(2) . . ?
C24 C25 H25A 109.3 . . ?
C26 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
C26 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
C25 C26 C21 110.1(2) . . ?
C25 C26 H26A 109.6 . . ?
C21 C26 H26A 109.6 . . ?
C25 C26 H26B 109.6 . . ?
C21 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
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 1.8935(16) . ?
Cu1 O1 1.8935(16) 3_665 ?
Cu1 N1 2.0236(18) 3_665 ?
Cu1 N1 2.0236(18) . ?
N1 C11 1.289(3) . ?
N1 C21 1.487(3) . ?
O1 C1 1.297(3) . ?
C1 C10 1.403(3) . ?
C1 C2 1.440(3) . ?
C2 C3 1.354(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.423(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.416(3) . ?
C4 C9 1.418(3) . ?
C5 C6 1.372(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.415(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.454(3) . ?
C10 C11 1.441(3) . ?
C11 H11 0.9500 . ?
C21 C22 1.530(3) . ?
C21 C26 1.532(3) . ?
C21 H21 1.0000 . ?
C22 C23 1.532(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.523(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.519(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.529(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 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 170.4(2) 3_665 . . . ?
N1 Cu1 O1 C1 -9.6(2) . . . . ?
Cu1 O1 C1 C10 2.2(3) . . . . ?
Cu1 O1 C1 C2 -178.76(15) . . . . ?
O1 C1 C2 C3 -178.7(2) . . . . ?
C10 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 -2.2(3) . . . . ?
C2 C3 C4 C5 -179.4(2) . . . . ?
C2 C3 C4 C9 0.1(3) . . . . ?
C9 C4 C5 C6 -0.9(3) . . . . ?
C3 C4 C5 C6 178.6(2) . . . . ?
C4 C5 C6 C7 -1.4(4) . . . . ?
C5 C6 C7 C8 1.5(4) . . . . ?
C6 C7 C8 C9 0.6(4) . . . . ?
C7 C8 C9 C4 -2.7(3) . . . . ?
C7 C8 C9 C10 177.1(2) . . . . ?
C5 C4 C9 C8 2.8(3) . . . . ?
C3 C4 C9 C8 -176.7(2) . . . . ?
C5 C4 C9 C10 -176.9(2) . . . . ?
C3 C4 C9 C10 3.6(3) . . . . ?
O1 C1 C10 C11 7.1(3) . . . . ?
C2 C1 C10 C11 -171.9(2) . . . . ?
O1 C1 C10 C9 -177.7(2) . . . . ?
C2 C1 C10 C9 3.3(3) . . . . ?
C8 C9 C10 C1 175.0(2) . . . . ?
C4 C9 C10 C1 -5.3(3) . . . . ?
C8 C9 C10 C11 -9.8(3) . . . . ?
C4 C9 C10 C11 170.0(2) . . . . ?
C21 N1 C11 C10 177.6(2) . . . . ?
Cu1 N1 C11 C10 -7.1(3) . . . . ?
C1 C10 C11 N1 -4.0(4) . . . . ?
C9 C10 C11 N1 -179.3(2) . . . . ?
C11 N1 C21 C22 11.9(3) . . . . ?
Cu1 N1 C21 C22 -163.72(16) . . . . ?
C11 N1 C21 C26 -113.0(2) . . . . ?
Cu1 N1 C21 C26 71.4(2) . . . . ?
N1 C21 C22 C23 173.6(2) . . . . ?
C26 C21 C22 C23 -61.3(3) . . . . ?
C21 C22 C23 C24 58.3(3) . . . . ?
C22 C23 C24 C25 -54.1(3) . . . . ?
C23 C24 C25 C26 52.7(3) . . . . ?
C24 C25 C26 C21 -56.3(3) . . . . ?
N1 C21 C26 C25 -169.71(19) . . . . ?
C22 C21 C26 C25 60.8(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168307285
