#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/51/2215189.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_2215189
loop_
_publ_author_name
'Bi-Rong Lian'
'Jun-Xia Li'
'Yi-Min Jiang'
'Bo-Lin Liang'
_publ_section_title
(2,2'-Bipyridine-κ²N,N')(1-formyl-2-naphtholato-κ²O,O')(nitrato-κO)copper(II)
_journal_coeditor_code           KP2125
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2358
_journal_page_last               m2358
_journal_paper_doi               10.1107/S1600536807039669
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu (C11 H7 O2) (N O3) (C10 H8 N2)]'
_chemical_formula_moiety         'C21 H15 Cu N3 O5'
_chemical_formula_sum            'C21 H15 Cu N3 O5'
_chemical_formula_weight         452.90
_chemical_name_systematic
;
(2,2'-Bipyridine-κ²N,N')(1-formyl-2-naphtholato-κ²O,O')(nitrato-\
\kO)copper(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 108.850(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.428(3)
_cell_length_b                   9.167(2)
_cell_length_c                   17.245(6)
_cell_measurement_reflns_used    38
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15.24
_cell_measurement_theta_min      4.61
_cell_volume                     1859.3(9)
_computing_cell_refinement       'XSCANS (Siemens, 1994)'
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        'SHELXTL (Siemens, 1994)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1994)'
_computing_publication_material  'SHELXTL (Siemens, 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3797
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.73
_diffrn_standards_decay_%        1.37
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.216
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_correction_T_min  0.7671
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.387
_refine_ls_extinction_coef       0.00014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0340
_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)+(0.0535P)²+0.0639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0932
_reflns_number_gt                2552
_reflns_number_total             3261
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2125.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2215189
_cod_database_fobs_code          2215189
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cu Cu 0.69710(3) 0.56548(4) 0.01255(2) 0.04165(14) Uani d . 1
O O1 0.57130(15) 0.6902(2) -0.03875(11) 0.0465(5) Uani d . 1
O O2 0.64002(17) 0.5217(2) 0.10181(12) 0.0488(5) Uani d . 1
O O3 0.8122(2) 0.7602(3) 0.05872(16) 0.0885(9) Uani d . 1
O O4 0.8697(3) 0.6778(3) 0.18001(17) 0.1045(10) Uani d . 1
O O5 0.9546(2) 0.8586(3) 0.14903(16) 0.0751(7) Uani d . 1
N N1 0.73773(19) 0.5505(3) -0.08999(14) 0.0424(5) Uani d . 1
N N2 0.81823(18) 0.4139(2) 0.04854(14) 0.0412(5) Uani d . 1
N N3 0.8786(2) 0.7689(3) 0.12895(18) 0.0549(7) Uani d . 1
C C1 0.5021(2) 0.7470(3) -0.00535(17) 0.0408(6) Uani d . 1
C C2 0.4219(2) 0.8518(3) -0.05254(18) 0.0473(7) Uani d . 1
H H2 0.4195 0.8722 -0.1059 0.057 Uiso calc R 1
C C3 0.3493(2) 0.9216(3) -0.02088(19) 0.0488(7) Uani d . 1
H H3 0.2982 0.9886 -0.0534 0.059 Uiso calc R 1
C C4 0.3487(2) 0.8958(3) 0.06057(18) 0.0448(7) Uani d . 1
C C5 0.2758(3) 0.9761(4) 0.0928(2) 0.0590(9) Uani d . 1
H H5 0.2281 1.0469 0.0609 0.071 Uiso calc R 1
C C6 0.2749(3) 0.9502(4) 0.1705(2) 0.0664(10) Uani d . 1
H H6 0.2272 1.0038 0.1915 0.080 Uiso calc R 1
C C7 0.3455(3) 0.8437(4) 0.2182(2) 0.0573(8) Uani d . 1
H H7 0.3438 0.8252 0.2708 0.069 Uiso calc R 1
C C8 0.4175(2) 0.7658(3) 0.18808(18) 0.0492(7) Uani d . 1
H H8 0.4647 0.6959 0.2212 0.059 Uiso calc R 1
C C9 0.4220(2) 0.7884(3) 0.10894(17) 0.0413(6) Uani d . 1
C C10 0.4987(2) 0.7101(3) 0.07414(17) 0.0390(6) Uani d . 1
C C11 0.5631(2) 0.5932(3) 0.11747(18) 0.0445(7) Uani d . 1
H H11 0.5467 0.5645 0.1642 0.053 Uiso calc R 1
C C12 0.6931(3) 0.6285(4) -0.15859(19) 0.0550(8) Uani d . 1
H H12 0.6364 0.6959 -0.1606 0.066 Uiso calc R 1
C C13 0.7278(3) 0.6129(4) -0.2256(2) 0.0678(10) Uani d . 1
H H13 0.6947 0.6684 -0.2724 0.081 Uiso calc R 1
C C14 0.8112(3) 0.5152(4) -0.2232(2) 0.0660(10) Uani d . 1
H H14 0.8362 0.5042 -0.2682 0.079 Uiso calc R 1
C C15 0.8582(3) 0.4327(3) -0.1540(2) 0.0563(8) Uani d . 1
H H15 0.9147 0.3647 -0.1518 0.068 Uiso calc R 1
C C16 0.8204(2) 0.4523(3) -0.08780(17) 0.0401(6) Uani d . 1
C C17 0.8641(2) 0.3727(3) -0.00911(17) 0.0418(6) Uani d . 1
C C18 0.9466(2) 0.2650(3) 0.0066(2) 0.0554(8) Uani d . 1
H H18 0.9769 0.2364 -0.0338 0.066 Uiso calc R 1
C C19 0.9828(3) 0.2011(4) 0.0830(2) 0.0625(9) Uani d . 1
H H19 1.0378 0.1282 0.0945 0.075 Uiso calc R 1
C C20 0.9380(3) 0.2448(4) 0.1418(2) 0.0585(8) Uani d . 1
H H20 0.9626 0.2031 0.1937 0.070 Uiso calc R 1
C C21 0.8559(2) 0.3514(3) 0.12283(18) 0.0506(7) Uani d . 1
H H21 0.8253 0.3814 0.1629 0.061 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
_geom_angle_publ_flag
O1 Cu O2 92.12(8) yes
O1 Cu N1 91.97(9) yes
O2 Cu N1 162.68(9) ?
O1 Cu N2 169.98(9) yes
O2 Cu N2 92.40(9) yes
N1 Cu N2 81.15(9) yes
O1 Cu O3 91.16(9) yes
O2 Cu O3 103.65(10) ?
N1 Cu O3 93.08(10) ?
N2 Cu O3 96.45(10) yes
C1 O1 Cu 126.84(18) ?
C11 O2 Cu 124.22(19) ?
N3 O3 Cu 123.0(2) ?
C12 N1 C16 118.2(2) ?
C12 N1 Cu 126.5(2) ?
C16 N1 Cu 115.28(18) ?
C21 N2 C17 119.0(2) ?
C21 N2 Cu 126.1(2) ?
C17 N2 Cu 114.94(18) ?
O5 N3 O3 122.5(3) ?
O5 N3 O4 119.4(3) ?
O3 N3 O4 118.0(3) ?
O1 C1 C10 124.4(2) ?
O1 C1 C2 117.3(3) ?
C10 C1 C2 118.2(2) ?
C3 C2 C1 121.3(3) ?
C3 C2 H2 119.4 ?
C1 C2 H2 119.4 ?
C2 C3 C4 122.3(3) ?
C2 C3 H3 118.9 ?
C4 C3 H3 118.9 ?
C5 C4 C9 120.2(3) ?
C5 C4 C3 120.6(3) ?
C9 C4 C3 119.2(3) ?
C6 C5 C4 120.4(3) ?
C6 C5 H5 119.8 ?
C4 C5 H5 119.8 ?
C5 C6 C7 120.0(3) ?
C5 C6 H6 120.0 ?
C7 C6 H6 120.0 ?
C8 C7 C6 120.4(3) ?
C8 C7 H7 119.8 ?
C6 C7 H7 119.8 ?
C7 C8 C9 121.9(3) ?
C7 C8 H8 119.1 ?
C9 C8 H8 119.1 ?
C8 C9 C4 117.2(3) ?
C8 C9 C10 124.2(3) ?
C4 C9 C10 118.6(3) ?
C11 C10 C1 120.3(2) ?
C11 C10 C9 119.4(3) ?
C1 C10 C9 120.2(2) ?
O2 C11 C10 128.8(3) ?
O2 C11 H11 115.6 ?
C10 C11 H11 115.6 ?
N1 C12 C13 122.6(3) ?
N1 C12 H12 118.7 ?
C13 C12 H12 118.7 ?
C14 C13 C12 119.3(3) ?
C14 C13 H13 120.4 ?
C12 C13 H13 120.4 ?
C13 C14 C15 119.6(3) ?
C13 C14 H14 120.2 ?
C15 C14 H14 120.2 ?
C14 C15 C16 119.0(3) ?
C14 C15 H15 120.5 ?
C16 C15 H15 120.5 ?
N1 C16 C15 121.4(3) ?
N1 C16 C17 113.8(2) ?
C15 C16 C17 124.9(3) ?
N2 C17 C18 121.2(3) ?
N2 C17 C16 114.8(2) ?
C18 C17 C16 124.0(3) ?
C19 C18 C17 118.8(3) ?
C19 C18 H18 120.6 ?
C17 C18 H18 120.6 ?
C20 C19 C18 120.0(3) ?
C20 C19 H19 120.0 ?
C18 C19 H19 120.0 ?
C19 C20 C21 118.8(3) ?
C19 C20 H20 120.6 ?
C21 C20 H20 120.6 ?
N2 C21 C20 122.2(3) ?
N2 C21 H21 118.9 ?
C20 C21 H21 118.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu O1 1.9082(18) yes
Cu O2 1.934(2) yes
Cu N1 1.994(2) yes
Cu N2 1.995(2) yes
Cu O3 2.265(3) yes
O1 C1 1.289(3) ?
O2 C11 1.259(3) ?
O3 N3 1.228(3) ?
O4 N3 1.244(4) ?
O5 N3 1.215(3) ?
N1 C12 1.339(4) ?
N1 C16 1.357(3) ?
N2 C21 1.342(4) ?
N2 C17 1.350(3) ?
C1 C10 1.426(4) ?
C1 C2 1.434(4) ?
C2 C3 1.356(4) ?
C2 H2 0.9300 ?
C3 C4 1.427(4) ?
C3 H3 0.9300 ?
C4 C5 1.414(4) ?
C4 C9 1.415(4) ?
C5 C6 1.363(5) ?
C5 H5 0.9300 ?
C6 C7 1.390(5) ?
C6 H6 0.9300 ?
C7 C8 1.372(4) ?
C7 H7 0.9300 ?
C8 C9 1.399(4) ?
C8 H8 0.9300 ?
C9 C10 1.468(4) ?
C10 C11 1.400(4) ?
C11 H11 0.9300 ?
C12 C13 1.365(4) ?
C12 H12 0.9300 ?
C13 C14 1.360(4) ?
C13 H13 0.9300 ?
C14 C15 1.374(4) ?
C14 H14 0.9300 ?
C15 C16 1.379(4) ?
C15 H15 0.9300 ?
C16 C17 1.481(4) ?
C17 C18 1.385(4) ?
C18 C19 1.378(4) ?
C18 H18 0.9300 ?
C19 C20 1.365(4) ?
C19 H19 0.9300 ?
C20 C21 1.375(4) ?
C20 H20 0.9300 ?
C21 H21 0.9300 ?
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
O2 Cu O1 C1 17.3(2)
N1 Cu O1 C1 -179.5(2)
N2 Cu O1 C1 134.1(4)
O3 Cu O1 C1 -86.4(2)
O1 Cu O2 C11 -14.7(2)
N1 Cu O2 C11 -118.3(3)
N2 Cu O2 C11 174.2(2)
O3 Cu O2 C11 77.0(2)
O1 Cu O3 N3 135.3(3)
O2 Cu O3 N3 42.8(3)
N1 Cu O3 N3 -132.7(3)
N2 Cu O3 N3 -51.3(3)
O1 Cu N1 C12 9.0(3)
O2 Cu N1 C12 112.6(3)
N2 Cu N1 C12 -178.3(3)
O3 Cu N1 C12 -82.3(3)
O1 Cu N1 C16 -172.13(19)
O2 Cu N1 C16 -68.5(4)
N2 Cu N1 C16 0.55(19)
O3 Cu N1 C16 96.6(2)
O1 Cu N2 C21 -134.5(4)
O2 Cu N2 C21 -17.7(2)
N1 Cu N2 C21 178.5(2)
O3 Cu N2 C21 86.3(2)
O1 Cu N2 C17 45.2(6)
O2 Cu N2 C17 161.98(19)
N1 Cu N2 C17 -1.86(18)
O3 Cu N2 C17 -94.0(2)
Cu O3 N3 O5 165.6(2)
Cu O3 N3 O4 -11.3(4)
Cu O1 C1 C10 -8.8(4)
Cu O1 C1 C2 172.60(18)
O1 C1 C2 C3 -177.1(3)
C10 C1 C2 C3 4.3(4)
C1 C2 C3 C4 0.2(4)
C2 C3 C4 C5 176.8(3)
C2 C3 C4 C9 -3.3(4)
C9 C4 C5 C6 -0.4(5)
C3 C4 C5 C6 179.5(3)
C4 C5 C6 C7 -0.5(5)
C5 C6 C7 C8 1.1(5)
C6 C7 C8 C9 -0.8(5)
C7 C8 C9 C4 0.0(4)
C7 C8 C9 C10 178.9(3)
C5 C4 C9 C8 0.6(4)
C3 C4 C9 C8 -179.3(3)
C5 C4 C9 C10 -178.3(3)
C3 C4 C9 C10 1.7(4)
O1 C1 C10 C11 -8.3(4)
C2 C1 C10 C11 170.3(2)
O1 C1 C10 C9 175.7(2)
C2 C1 C10 C9 -5.7(4)
C8 C9 C10 C11 7.8(4)
C4 C9 C10 C11 -173.3(2)
C8 C9 C10 C1 -176.1(3)
C4 C9 C10 C1 2.7(4)
Cu O2 C11 C10 3.8(4)
C1 C10 C11 O2 11.0(4)
C9 C10 C11 O2 -173.0(3)
C16 N1 C12 C13 -0.1(5)
Cu N1 C12 C13 178.7(3)
N1 C12 C13 C14 -0.3(6)
C12 C13 C14 C15 0.7(6)
C13 C14 C15 C16 -0.7(5)
C12 N1 C16 C15 0.1(4)
Cu N1 C16 C15 -178.8(2)
C12 N1 C16 C17 179.7(3)
Cu N1 C16 C17 0.7(3)
C14 C15 C16 N1 0.3(5)
C14 C15 C16 C17 -179.2(3)
C21 N2 C17 C18 1.8(4)
Cu N2 C17 C18 -177.9(2)
C21 N2 C17 C16 -177.5(2)
Cu N2 C17 C16 2.8(3)
N1 C16 C17 N2 -2.3(3)
C15 C16 C17 N2 177.2(3)
N1 C16 C17 C18 178.4(3)
C15 C16 C17 C18 -2.1(5)
N2 C17 C18 C19 -0.9(5)
C16 C17 C18 C19 178.3(3)
C17 C18 C19 C20 -0.4(5)
C18 C19 C20 C21 0.8(5)
C17 N2 C21 C20 -1.3(4)
Cu N2 C21 C20 178.3(2)
C19 C20 C21 N2 0.1(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168309293
