#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/27/2012751.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_2012751
loop_
_publ_author_name
'Zavalij, Peter Y.'
'Burton, Benjamin L.'
'Jones Jr, Wayne E.'
_publ_section_title
;
 New structures in the bipyridine--copper(II) nitrate--methanol system:
 [(bpy)₂Cu(NO₃)]NO₃·CH₃OH and [(bpy)₂Cu(NO₃)]NO₃
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m330
_journal_page_last               m333
_journal_paper_doi               10.1107/S010827010200690X
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          '[Cu (N O3) (C10 H8 N2)2] (N O3), C H4 O'
_chemical_formula_moiety         'C20 H16 Cu N5 O3 1+, N1 O3 1-, C1 H4 O1'
_chemical_formula_sum            'C21 H20 Cu N6 O7'
_chemical_formula_weight         531.97
_chemical_name_common            I
_chemical_name_systematic
;
bis(2,2'-bipyridine)nitrocopper(II) nitrate methanol solvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-97 and ZCIF by Peter Y. Zavalij'
_cell_angle_alpha                109.492(3)
_cell_angle_beta                 92.902(4)
_cell_angle_gamma                101.347(4)
_cell_formula_units_Z            2
_cell_length_a                   7.6862(6)
_cell_length_b                   11.8902(9)
_cell_length_c                   13.3644(11)
_cell_measurement_reflns_used    6220
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.09
_cell_measurement_theta_min      2.74
_cell_volume                     1119.90(16)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Materials Studio (Accelrys, 2001)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Smart CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22064
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         1.63
_diffrn_standards_decay_%        -0.78
_exptl_absorpt_coefficient_mu    1.032
_exptl_absorpt_correction_T_max  0.7041
_exptl_absorpt_correction_T_min  0.6340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             546
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6676
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0637P)²+0.0117P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1001
_reflns_number_gt                5643
_reflns_number_total             6676
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fr1363.cif
_cod_data_source_block           I
_cod_original_cell_volume        1119.9(2)
_cod_database_code               2012751
_cod_database_fobs_code          2012751
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
Cu1 0.23697(2) 0.84996(2) 0.72600(2) 0.01783(7) Uani d . 1 . . Cu
N1 0.20965(17) 0.90586(11) 0.60414(10) 0.0176(2) Uani d . 1 . . N
N2 0.03918(17) 0.70911(11) 0.63335(10) 0.0178(2) Uani d . 1 . . N
C1 0.3068(2) 1.00953(13) 0.59701(13) 0.0204(3) Uani d D 1 . . C
H1 0.383(2) 1.0646(13) 0.6562(11) 0.016(4) Uiso d D 1 . . H
C2 0.2943(2) 1.03614(14) 0.50417(13) 0.0225(3) Uani d D 1 . . C
H2 0.359(2) 1.1072(13) 0.5014(16) 0.023(5) Uiso d D 1 . . H
C3 0.1821(2) 0.95205(15) 0.41525(13) 0.0246(3) Uani d D 1 . . C
H3 0.180(3) 0.9696(18) 0.3529(11) 0.025(5) Uiso d D 1 . . H
C4 0.0809(2) 0.84512(14) 0.42264(12) 0.0223(3) Uani d D 1 . . C
H4 0.004(2) 0.7905(15) 0.3646(12) 0.026(5) Uiso d D 1 . . H
C5 0.0959(2) 0.82492(13) 0.51849(12) 0.0173(3) Uani d . 1 . . C
C6 -0.0085(2) 0.71725(12) 0.53801(12) 0.0174(3) Uani d . 1 . . C
C7 -0.1515(2) 0.63364(14) 0.46644(13) 0.0211(3) Uani d D 1 . . C
H7 -0.186(3) 0.641(2) 0.4030(12) 0.039(6) Uiso d D 1 . . H
C8 -0.2482(2) 0.54013(14) 0.49463(13) 0.0236(3) Uani d D 1 . . C
H8 -0.3473(19) 0.4880(15) 0.4492(13) 0.021(5) Uiso d D 1 . . H
C9 -0.2005(2) 0.53210(14) 0.59280(14) 0.0244(3) Uani d D 1 . . C
H9 -0.267(3) 0.4715(16) 0.6124(17) 0.037(6) Uiso d D 1 . . H
C10 -0.0561(2) 0.61838(14) 0.66021(13) 0.0211(3) Uani d D 1 . . C
H10 -0.018(2) 0.6158(17) 0.7257(11) 0.024(5) Uiso d D 1 . . H
N3 0.20821(17) 1.00164(11) 0.85517(10) 0.0187(2) Uani d . 1 . . N
N4 0.28029(17) 0.79062(11) 0.84546(10) 0.0188(2) Uani d . 1 . . N
C11 0.1674(2) 1.10588(14) 0.85359(13) 0.0219(3) Uani d D 1 . . C
H11 0.153(3) 1.1169(17) 0.7885(11) 0.025(5) Uiso d D 1 . . H
C12 0.1542(2) 1.20003(14) 0.94589(14) 0.0245(3) Uani d D 1 . . C
H12 0.134(3) 1.2717(14) 0.9415(18) 0.037(6) Uiso d D 1 . . H
C13 0.1819(2) 1.18545(15) 1.04342(14) 0.0242(3) Uani d D 1 . . C
H13 0.179(3) 1.2488(14) 1.1031(12) 0.031(5) Uiso d D 1 . . H
C14 0.2227(2) 1.07764(14) 1.04623(12) 0.0216(3) Uani d D 1 . . C
H14 0.234(2) 1.0618(16) 1.1091(10) 0.015(4) Uiso d D 1 . . H
C15 0.23571(19) 0.98758(13) 0.95023(12) 0.0179(3) Uani d . 1 . . C
C16 0.2819(2) 0.87042(13) 0.94511(12) 0.0184(3) Uani d . 1 . . C
C17 0.3268(2) 0.84372(15) 1.03520(13) 0.0223(3) Uani d D 1 . . C
H17 0.331(3) 0.9019(15) 1.1019(11) 0.031(5) Uiso d D 1 . . H
C18 0.3707(2) 0.73237(15) 1.02250(14) 0.0249(3) Uani d D 1 . . C
H18 0.389(3) 0.7073(19) 1.0788(13) 0.036(6) Uiso d D 1 . . H
C19 0.3713(2) 0.65154(15) 0.92011(14) 0.0253(3) Uani d D 1 . . C
H19 0.404(3) 0.5799(15) 0.913(2) 0.048(7) Uiso d D 1 . . H
C20 0.3259(2) 0.68346(14) 0.83389(13) 0.0225(3) Uani d D 1 . . C
H20 0.326(3) 0.6331(15) 0.7651(10) 0.021(5) Uiso d D 1 . . H
N5 0.58575(18) 0.83052(11) 0.68538(10) 0.0197(3) Uani d . 1 . . N
O1 0.52226(15) 0.91958(10) 0.74332(9) 0.0207(2) Uani d . 1 . . O
O2 0.47839(17) 0.73615(10) 0.62568(10) 0.0312(3) Uani d . 1 . . O
O3 0.74983(15) 0.84163(11) 0.69178(10) 0.0256(2) Uani d . 1 . . O
N6 0.4511(2) 0.33854(12) 0.73714(11) 0.0259(3) Uani d . 1 . . N
O4 0.28982(18) 0.29812(13) 0.74079(12) 0.0384(3) Uani d . 1 . . O
O5 0.50345(19) 0.44698(11) 0.74038(12) 0.0365(3) Uani d . 1 . . O
O6 0.55977(19) 0.27295(12) 0.73075(13) 0.0410(3) Uani d . 1 . . O
C1M 0.9560(3) 0.43745(17) 0.84539(18) 0.0343(4) Uani d D 1 . . C
H1M 0.888(3) 0.3582(14) 0.8351(17) 0.029(5) Uiso d D 1 . . H
H2M 1.043(3) 0.461(2) 0.9044(17) 0.062(8) Uiso d D 1 . . H
H3M 1.011(3) 0.434(2) 0.7825(15) 0.053(7) Uiso d D 1 . . H
O1M 0.8485(2) 0.52427(12) 0.86747(12) 0.0354(3) Uani d . 1 . . O
H4M 0.764(3) 0.497(2) 0.831(2) 0.039(7) Uiso d . 1 . . H
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_3
_geom_angle
N1 Cu1 N4 . 176.01(5)
N1 Cu1 N2 . 81.64(5)
N4 Cu1 N2 . 99.45(5)
N1 Cu1 N3 . 102.09(5)
N4 Cu1 N3 . 80.39(5)
N2 Cu1 N3 . 126.64(5)
N1 Cu1 O1 . 89.43(5)
N4 Cu1 O1 . 87.35(5)
N2 Cu1 O1 . 141.56(4)
N3 Cu1 O1 . 91.77(4)
N1 Cu1 O2 . 86.76(5)
N4 Cu1 O2 . 89.39(5)
N2 Cu1 O2 . 89.82(4)
N3 Cu1 O2 . 143.16(4)
O1 Cu1 O2 . 52.22(4)
C1 N1 C5 . 119.51(13)
C1 N1 Cu1 . 125.07(10)
C5 N1 Cu1 . 115.05(10)
C10 N2 C6 . 118.67(13)
C10 N2 Cu1 . 127.46(11)
C6 N2 Cu1 . 113.58(10)
N1 C1 C2 . 121.83(14)
N1 C1 H1 . 118.8(11)
C2 C1 H1 . 119.4(11)
C1 C2 C3 . 118.95(15)
C1 C2 H2 . 120.5(13)
C3 C2 H2 . 120.6(13)
C2 C3 C4 . 119.28(15)
C2 C3 H3 . 117.8(13)
C4 C3 H3 . 123.0(12)
C5 C4 C3 . 119.10(14)
C5 C4 H4 . 121.5(13)
C3 C4 H4 . 119.4(13)
N1 C5 C4 . 121.29(14)
N1 C5 C6 . 114.23(13)
C4 C5 C6 . 124.47(13)
N2 C6 C7 . 121.99(14)
N2 C6 C5 . 114.86(12)
C7 C6 C5 . 123.07(14)
C8 C7 C6 . 118.90(15)
C8 C7 H7 . 119.4(14)
C6 C7 H7 . 121.7(14)
C7 C8 C9 . 119.26(15)
C7 C8 H8 . 118.8(12)
C9 C8 H8 . 121.9(12)
C8 C9 C10 . 118.84(15)
C8 C9 H9 . 119.1(14)
C10 C9 H9 . 122.0(14)
N2 C10 C9 . 122.34(15)
N2 C10 H10 . 115.8(12)
C9 C10 H10 . 121.9(12)
C11 N3 C15 . 118.67(13)
C20 N4 C16 . 118.93(13)
N3 C11 C12 . 122.64(15)
N3 C11 H11 . 118.7(12)
C12 C11 H11 . 118.6(12)
Cu1 C11 H11 . 87.0(12)
C13 C12 C11 . 118.68(15)
C13 C12 H12 . 121.5(15)
C11 C12 H12 . 119.8(15)
C12 C13 C14 . 119.32(14)
C12 C13 H13 . 117.9(13)
C14 C13 H13 . 122.7(13)
C13 C14 C15 . 118.77(15)
C13 C14 H14 . 122.1(11)
C15 C14 H14 . 119.0(11)
N3 C15 C14 . 121.91(14)
N3 C15 C16 . 115.31(12)
C14 C15 C16 . 122.78(14)
N4 C16 C17 . 121.47(14)
N4 C16 C15 . 115.23(13)
C17 C16 C15 . 123.29(13)
C16 C17 C18 . 119.20(14)
C16 C17 H17 . 118.9(13)
C18 C17 H17 . 121.8(13)
C19 C18 C17 . 119.10(15)
C19 C18 H18 . 118.4(14)
C17 C18 H18 . 122.3(14)
C20 C19 C18 . 118.95(15)
C20 C19 H19 . 123.0(16)
C18 C19 H19 . 118.0(16)
N4 C20 C19 . 122.34(15)
N4 C20 H20 . 116.0(12)
C19 C20 H20 . 121.6(12)
O3 N5 O2 . 122.87(13)
O3 N5 O1 . 118.98(12)
O2 N5 O1 . 118.14(13)
N5 O1 Cu1 . 106.06(9)
N5 O2 Cu1 . 83.01(8)
N5 O3 Cu1 1_655 173.72(10)
O6 N6 O4 . 120.52(15)
O6 N6 O5 . 119.88(15)
O4 N6 O5 . 119.60(15)
O1m C1m H1m . 111.5(13)
O1m C1m H2m . 107.6(17)
H1m C1m H2m . 109(2)
O1m C1m H3m . 110.6(16)
H1m C1m H3m . 108(2)
H2m C1m H3m . 110(2)
C1m O1m H4m . 108(2)
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 N1 . 1.9700(10) yes
Cu1 N4 . 1.9870(10) yes
Cu1 N2 . 2.0180(10) yes
Cu1 N3 . 2.0980(10) yes
Cu1 O1 . 2.1570(10) yes
Cu1 O2 . 2.6650(10) yes
N1 C1 . 1.345(2) ?
N1 C5 . 1.354(2) ?
N2 C10 . 1.343(2) ?
N2 C6 . 1.348(2) ?
C1 C2 . 1.382(2) ?
C1 H1 . 0.924(10) ?
C2 C3 . 1.386(2) ?
C2 H2 . 0.905(11) ?
C3 C4 . 1.391(2) ?
C3 H3 . 0.925(11) ?
C4 C5 . 1.383(2) ?
C4 H4 . 0.915(11) ?
C5 C6 . 1.480(2) ?
C6 C7 . 1.393(2) ?
C7 C8 . 1.383(2) ?
C7 H7 . 0.914(11) ?
C8 C9 . 1.383(2) ?
C8 H8 . 0.921(10) ?
C9 C10 . 1.389(2) ?
C9 H9 . 0.920(11) ?
C10 H10 . 0.921(10) ?
N3 C11 . 1.3435(19) ?
N3 C15 . 1.347(2) ?
N4 C20 . 1.3491(19) ?
N4 C16 . 1.3507(19) ?
C11 C12 . 1.386(2) ?
C11 H11 . 0.926(11) ?
C12 C13 . 1.383(3) ?
C12 H12 . 0.916(11) ?
C13 C14 . 1.390(2) ?
C13 H13 . 0.902(11) ?
C14 C15 . 1.393(2) ?
C14 H14 . 0.924(10) ?
C15 C16 . 1.485(2) ?
C16 C17 . 1.388(2) ?
C17 C18 . 1.388(2) ?
C17 H17 . 0.922(11) ?
C18 C19 . 1.386(2) ?
C18 H18 . 0.911(11) ?
C19 C20 . 1.377(2) ?
C19 H19 . 0.911(11) ?
C20 H20 . 0.914(10) ?
N5 O3 . 1.2374(17) ?
N5 O2 . 1.2442(17) ?
N5 O1 . 1.2860(16) ?
N6 O6 . 1.2376(19) ?
N6 O4 . 1.248(2) ?
N6 O5 . 1.2582(18) ?
C1M O1M . 1.412(2) ?
C1M H1M . 0.944(14) ?
C1M H2M . 0.933(15) ?
C1M H3M . 0.952(15) ?
O1M H4M . 0.74(3) ?
Cu1 Cu1 1_655 7.6862(6) yes
Cu1 Cu1 1_455 7.6862(6) ?
Cu1 Cu1 2_677 7.5234(6) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1m H4m O5 . 0.74(3) 2.15(3) 2.882(2) 170(3) yes
C1m H3m O4 1_655 0.95(2) 2.90(2) 3.431(3) 116(2) yes
C1m H1m O6 . 0.940(10) 2.65(2) 3.261(3) 123(2) yes
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_publ_flag
N1 C5 C6 N2 -7.04(18) yes
C4 C5 C6 C7 -9.5(2) yes
N3 C15 C16 N4 -3.58(19) yes
C14 C15 C16 C17 -4.1(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139058582
