#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/70/2227078.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_2227078
loop_
_publ_author_name
'Ji, Xiao-Hui'
'Lu, Jiu-Fu'
_publ_section_title
;
 Bis[2-(cyclopentyliminomethyl)-5-methoxyphenolato]copper(II)
;
_journal_coeditor_code           SJ5030
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m881
_journal_paper_doi               10.1107/S1600536810025481
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Cu (C13 H16 N O2)2]'
_chemical_formula_moiety         'C26 H32 Cu N2 O4'
_chemical_formula_sum            'C26 H32 Cu N2 O4'
_chemical_formula_weight         500.08
_chemical_name_systematic
;
Bis[2-(cyclopentyliminomethyl)-5-methoxyphenolato]copper(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.236(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4960(10)
_cell_length_b                   14.054(2)
_cell_length_c                   20.442(2)
_cell_measurement_reflns_used    3695
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      2.5
_cell_volume                     2402.0(5)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_sigmaI/netI    0.0770
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12222
_diffrn_reflns_theta_full        25.28
_diffrn_reflns_theta_max         25.28
_diffrn_reflns_theta_min         1.77
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.944
_exptl_absorpt_correction_T_max  0.8264
_exptl_absorpt_correction_T_min  0.8122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1052
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.687
_refine_diff_density_min         -1.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0574
_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)+(0.0973P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1629
_reflns_number_gt                3131
_reflns_number_total             4333
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5030.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2227078
_cod_database_fobs_code          2227078
loop_
_symmetry_equiv_pos_as_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 -0.00311(5) 0.84349(3) 0.75910(2) 0.0392(2) Uani d . 1 . .
N N1 -0.0266(3) 0.8673(2) 0.85224(14) 0.0387(7) Uani d . 1 . .
N N2 0.0215(3) 0.8950(2) 0.67202(13) 0.0367(7) Uani d . 1 . .
O O1 0.2109(3) 0.80068(19) 0.77995(11) 0.0460(6) Uani d . 1 . .
O O2 0.6781(3) 0.6732(2) 0.91142(15) 0.0597(8) Uani d . 1 . .
O O3 -0.2181(3) 0.8050(2) 0.73199(11) 0.0487(7) Uani d . 1 . .
O O4 -0.6953(3) 0.7268(2) 0.58341(13) 0.0608(8) Uani d . 1 . .
C C1 0.2376(4) 0.8058(3) 0.89943(16) 0.0387(8) Uani d . 1 . .
C C2 0.2940(4) 0.7847(2) 0.83963(16) 0.0376(8) Uani d . 1 . .
C C3 0.4436(4) 0.7414(2) 0.84350(17) 0.0408(8) Uani d . 1 . .
H H3 0.4817 0.7276 0.8047 0.049 Uiso calc R 1 . .
C C4 0.5355(4) 0.7190(3) 0.90438(18) 0.0438(9) Uani d . 1 . .
C C5 0.4826(5) 0.7423(3) 0.96339(18) 0.0510(10) Uani d . 1 . .
H H5 0.5457 0.7289 1.0044 0.061 Uiso calc R 1 . .
C C6 0.3390(4) 0.7843(3) 0.96003(18) 0.0481(10) Uani d . 1 . .
H H6 0.3051 0.7999 0.9995 0.058 Uiso calc R 1 . .
C C7 0.7322(5) 0.6397(3) 0.8541(2) 0.0614(12) Uani d . 1 . .
H H7A 0.6525 0.5990 0.8293 0.092 Uiso calc R 1 . .
H H7B 0.8297 0.6046 0.8671 0.092 Uiso calc R 1 . .
H H7C 0.7513 0.6928 0.8270 0.092 Uiso calc R 1 . .
C C8 0.0844(4) 0.8467(2) 0.90186(18) 0.0404(9) Uani d . 1 . .
H H8 0.0625 0.8599 0.9439 0.049 Uiso calc R 1 . .
C C9 -0.1767(4) 0.9093(3) 0.86370(17) 0.0414(8) Uani d . 1 . .
H H9 -0.2630 0.8665 0.8436 0.050 Uiso calc R 1 . .
C C10 -0.2091(5) 1.0059(3) 0.8299(2) 0.0653(12) Uani d . 1 . .
H H10A -0.1117 1.0433 0.8349 0.078 Uiso calc R 1 . .
H H10B -0.2508 0.9980 0.7828 0.078 Uiso calc R 1 . .
C C11 -0.3317(6) 1.0539(4) 0.8645(3) 0.0819(16) Uani d . 1 . .
H H11A -0.2954 1.1169 0.8796 0.098 Uiso calc R 1 . .
H H11B -0.4332 1.0599 0.8344 0.098 Uiso calc R 1 . .
C C12 -0.3499(5) 0.9915(3) 0.9232(2) 0.0670(13) Uani d . 1 . .
H H12A -0.4458 0.9529 0.9131 0.080 Uiso calc R 1 . .
H H12B -0.3555 1.0298 0.9622 0.080 Uiso calc R 1 . .
C C13 -0.2011(5) 0.9294(3) 0.9345(2) 0.0563(11) Uani d . 1 . .
H H13A -0.2186 0.8711 0.9575 0.068 Uiso calc R 1 . .
H H13B -0.1102 0.9629 0.9596 0.068 Uiso calc R 1 . .
C C14 -0.2496(4) 0.8557(2) 0.61796(17) 0.0393(9) Uani d . 1 . .
C C15 -0.3019(4) 0.8089(3) 0.67175(17) 0.0390(8) Uani d . 1 . .
C C16 -0.4528(4) 0.7646(3) 0.66019(17) 0.0432(9) Uani d . 1 . .
H H16 -0.4880 0.7324 0.6947 0.052 Uiso calc R 1 . .
C C17 -0.5492(4) 0.7683(3) 0.59848(18) 0.0448(9) Uani d . 1 . .
C C18 -0.4993(5) 0.8175(3) 0.54602(19) 0.0540(11) Uani d . 1 . .
H H18 -0.5656 0.8213 0.5047 0.065 Uiso calc R 1 . .
C C19 -0.3540(4) 0.8592(3) 0.55627(18) 0.0497(10) Uani d . 1 . .
H H19 -0.3216 0.8916 0.5213 0.060 Uiso calc R 1 . .
C C20 -0.7465(6) 0.6658(3) 0.6315(3) 0.0699(14) Uani d . 1 . .
H H20A -0.6642 0.6202 0.6469 0.105 Uiso calc R 1 . .
H H20B -0.8423 0.6332 0.6115 0.105 Uiso calc R 1 . .
H H20C -0.7675 0.7032 0.6683 0.105 Uiso calc R 1 . .
C C21 -0.0928(4) 0.8941(2) 0.62103(17) 0.0400(8) Uani d . 1 . .
H H21 -0.0707 0.9215 0.5822 0.048 Uiso calc R 1 . .
C C22 0.1781(4) 0.9340(2) 0.66504(17) 0.0386(8) Uani d . 1 . .
H H22 0.2540 0.8808 0.6702 0.046 Uiso calc R 1 . .
C C23 0.1945(4) 0.9857(3) 0.60076(18) 0.0472(9) Uani d . 1 . .
H H23A 0.1985 0.9408 0.5651 0.057 Uiso calc R 1 . .
H H23B 0.1057 1.0290 0.5873 0.057 Uiso calc R 1 . .
C C24 0.3521(5) 1.0401(3) 0.6185(2) 0.0557(11) Uani d . 1 . .
H H24A 0.3421 1.1032 0.5989 0.067 Uiso calc R 1 . .
H H24B 0.4372 1.0065 0.6022 0.067 Uiso calc R 1 . .
C C25 0.3882(5) 1.0467(3) 0.6946(2) 0.0631(12) Uani d . 1 . .
H H25A 0.4823 1.0096 0.7124 0.076 Uiso calc R 1 . .
H H25B 0.4067 1.1123 0.7087 0.076 Uiso calc R 1 . .
C C26 0.2415(5) 1.0072(3) 0.71846(19) 0.0493(10) Uani d . 1 . .
H H26A 0.1632 1.0567 0.7208 0.059 Uiso calc R 1 . .
H H26B 0.2703 0.9774 0.7617 0.059 Uiso calc R 1 . .
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'
Cu Cu 0.3201 1.2651 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O3 . . 144.60(13) y
O1 Cu1 N2 . . 93.93(11) y
O3 Cu1 N2 . . 95.32(11) y
O1 Cu1 N1 . . 95.40(11) y
O3 Cu1 N1 . . 94.20(11) y
N2 Cu1 N1 . . 148.66(12) y
C8 N1 C9 . . 120.1(3) ?
C8 N1 Cu1 . . 122.4(2) ?
C9 N1 Cu1 . . 117.6(2) ?
C21 N2 C22 . . 119.3(3) ?
C21 N2 Cu1 . . 122.7(2) ?
C22 N2 Cu1 . . 118.0(2) ?
C2 O1 Cu1 . . 126.8(2) ?
C4 O2 C7 . . 119.1(3) ?
C15 O3 Cu1 . . 126.8(2) ?
C17 O4 C20 . . 118.7(3) ?
C6 C1 C2 . . 117.6(3) ?
C6 C1 C8 . . 118.2(3) ?
C2 C1 C8 . . 124.1(3) ?
O1 C2 C3 . . 117.4(3) ?
O1 C2 C1 . . 123.7(3) ?
C3 C2 C1 . . 118.9(3) ?
C4 C3 C2 . . 120.8(3) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
O2 C4 C3 . . 123.7(4) ?
O2 C4 C5 . . 115.9(3) ?
C3 C4 C5 . . 120.4(3) ?
C6 C5 C4 . . 119.1(3) ?
C6 C5 H5 . . 120.5 ?
C4 C5 H5 . . 120.5 ?
C5 C6 C1 . . 123.1(4) ?
C5 C6 H6 . . 118.5 ?
C1 C6 H6 . . 118.5 ?
O2 C7 H7A . . 109.5 ?
O2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N1 C8 C1 . . 127.2(3) ?
N1 C8 H8 . . 116.4 ?
C1 C8 H8 . . 116.4 ?
N1 C9 C13 . . 119.8(3) ?
N1 C9 C10 . . 112.2(3) ?
C13 C9 C10 . . 102.8(3) ?
N1 C9 H9 . . 107.1 ?
C13 C9 H9 . . 107.1 ?
C10 C9 H9 . . 107.1 ?
C11 C10 C9 . . 105.5(3) ?
C11 C10 H10A . . 110.6 ?
C9 C10 H10A . . 110.6 ?
C11 C10 H10B . . 110.6 ?
C9 C10 H10B . . 110.6 ?
H10A C10 H10B . . 108.8 ?
C12 C11 C10 . . 106.7(4) ?
C12 C11 H11A . . 110.4 ?
C10 C11 H11A . . 110.4 ?
C12 C11 H11B . . 110.4 ?
C10 C11 H11B . . 110.4 ?
H11A C11 H11B . . 108.6 ?
C11 C12 C13 . . 104.6(3) ?
C11 C12 H12A . . 110.8 ?
C13 C12 H12A . . 110.8 ?
C11 C12 H12B . . 110.8 ?
C13 C12 H12B . . 110.8 ?
H12A C12 H12B . . 108.9 ?
C12 C13 C9 . . 102.3(3) ?
C12 C13 H13A . . 111.3 ?
C9 C13 H13A . . 111.3 ?
C12 C13 H13B . . 111.3 ?
C9 C13 H13B . . 111.3 ?
H13A C13 H13B . . 109.2 ?
C19 C14 C15 . . 118.5(3) ?
C19 C14 C21 . . 117.4(3) ?
C15 C14 C21 . . 124.0(3) ?
O3 C15 C16 . . 117.8(3) ?
O3 C15 C14 . . 123.7(3) ?
C16 C15 C14 . . 118.5(3) ?
C17 C16 C15 . . 120.8(3) ?
C17 C16 H16 . . 119.6 ?
C15 C16 H16 . . 119.6 ?
O4 C17 C16 . . 124.2(3) ?
O4 C17 C18 . . 115.3(3) ?
C16 C17 C18 . . 120.5(3) ?
C19 C18 C17 . . 119.2(3) ?
C19 C18 H18 . . 120.4 ?
C17 C18 H18 . . 120.4 ?
C18 C19 C14 . . 122.5(4) ?
C18 C19 H19 . . 118.8 ?
C14 C19 H19 . . 118.8 ?
O4 C20 H20A . . 109.5 ?
O4 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
O4 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
N2 C21 C14 . . 126.9(3) ?
N2 C21 H21 . . 116.5 ?
C14 C21 H21 . . 116.5 ?
N2 C22 C26 . . 113.1(3) ?
N2 C22 C23 . . 118.9(3) ?
C26 C22 C23 . . 102.7(3) ?
N2 C22 H22 . . 107.2 ?
C26 C22 H22 . . 107.2 ?
C23 C22 H22 . . 107.2 ?
C24 C23 C22 . . 104.1(3) ?
C24 C23 H23A . . 110.9 ?
C22 C23 H23A . . 110.9 ?
C24 C23 H23B . . 110.9 ?
C22 C23 H23B . . 110.9 ?
H23A C23 H23B . . 109.0 ?
C23 C24 C25 . . 106.2(3) ?
C23 C24 H24A . . 110.5 ?
C25 C24 H24A . . 110.5 ?
C23 C24 H24B . . 110.5 ?
C25 C24 H24B . . 110.5 ?
H24A C24 H24B . . 108.7 ?
C26 C25 C24 . . 106.0(3) ?
C26 C25 H25A . . 110.5 ?
C24 C25 H25A . . 110.5 ?
C26 C25 H25B . . 110.5 ?
C24 C25 H25B . . 110.5 ?
H25A C25 H25B . . 108.7 ?
C25 C26 C22 . . 102.8(3) ?
C25 C26 H26A . . 111.2 ?
C22 C26 H26A . . 111.2 ?
C25 C26 H26B . . 111.2 ?
C22 C26 H26B . . 111.2 ?
H26A C26 H26B . . 109.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 . 1.890(2) y
Cu1 O3 . 1.891(2) y
Cu1 N2 . 1.967(3) y
Cu1 N1 . 1.978(3) y
N1 C8 . 1.289(4) ?
N1 C9 . 1.462(4) ?
N2 C21 . 1.292(4) ?
N2 C22 . 1.469(4) ?
O1 C2 . 1.316(4) ?
O2 C4 . 1.356(4) ?
O2 C7 . 1.414(5) ?
O3 C15 . 1.309(4) ?
O4 C17 . 1.356(4) ?
O4 C20 . 1.429(5) ?
C1 C6 . 1.410(5) ?
C1 C2 . 1.421(5) ?
C1 C8 . 1.432(5) ?
C2 C3 . 1.398(5) ?
C3 C4 . 1.383(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.399(5) ?
C5 C6 . 1.346(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 H8 . 0.9300 ?
C9 C13 . 1.524(5) ?
C9 C10 . 1.527(5) ?
C9 H9 . 0.9800 ?
C10 C11 . 1.518(6) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.516(6) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.520(6) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C19 . 1.408(5) ?
C14 C15 . 1.419(5) ?
C14 C21 . 1.428(5) ?
C15 C16 . 1.407(5) ?
C16 C17 . 1.378(5) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.403(5) ?
C18 C19 . 1.349(5) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C21 H21 . 0.9300 ?
C22 C26 . 1.527(5) ?
C22 C23 . 1.529(5) ?
C22 H22 . 0.9800 ?
C23 C24 . 1.529(5) ?
C23 H23A . 0.9700 ?
C23 H23B . 0.9700 ?
C24 C25 . 1.535(6) ?
C24 H24A . 0.9700 ?
C24 H24B . 0.9700 ?
C25 C26 . 1.522(5) ?
C25 H25A . 0.9700 ?
C25 H25B . 0.9700 ?
C26 H26A . 0.9700 ?
C26 H26B . 0.9700 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079426
