#------------------------------------------------------------------------------
#$Date: 2026-04-08 03:20:30 +0200 (Wed 08 de Apr de 2026) $
#$Revision: 305479 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/18/7251864.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7251864
loop_
_publ_author_name
'Kuncová, Lucie'
'Lazarová, Jana'
'Kotek, Jan'
'Kubíček, Vojtěch'
'Hermann, Petr'
_publ_section_title
;
 Dipyridinophane ligands -- synthesis and coordination study
;
_journal_issue                   20
_journal_name_full               'RSC Advances'
_journal_page_first              18220
_journal_page_last               18231
_journal_paper_doi               10.1039/D6RA00469E
_journal_volume                  16
_journal_year                    2026
_chemical_formula_moiety         'C18 H18 Cu N4 O4, 2(H2 O)'
_chemical_formula_sum            'C18 H22 Cu N4 O6'
_chemical_formula_weight         453.93
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2026-02-20 deposited with the CCDC.	2026-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.1190(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.7157(12)
_cell_length_b                   9.7356(4)
_cell_length_c                   13.7443(6)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.2783
_cell_measurement_theta_min      2.5725
_cell_volume                     3756.9(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service v8.5.1.2 Release'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'XT, VERSION 2018/2'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 7.391
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            104898
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.298
_diffrn_reflns_theta_min         2.214
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'INCOATEC I\mS'
_exptl_absorpt_coefficient_mu    1.208
_exptl_absorpt_correction_T_max  0.78
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            green-blue
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_description       prism
_exptl_crystal_F_000             1880
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.214
_refine_diff_density_max         0.999
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4661
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0342P)²+6.8649P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0719
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4572
_reflns_number_total             4661
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6ra00469e2.cif
_cod_data_source_block           py2n2_karboxcu
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7251864
_shelx_shelxl_version_number     2017/1
_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   0.650
_shelx_estimated_absorpt_t_max   0.782
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.62705(2) 0.35480(2) 0.27201(2) 0.01659(6) Uani 1 1 d . . . . .
N1 N 0.66822(4) 0.26907(13) 0.40134(9) 0.0175(2) Uani 1 1 d . . . . .
C2 C 0.69069(5) 0.15000(15) 0.40196(11) 0.0199(3) Uani 1 1 d . . . . .
C3 C 0.68823(6) 0.08966(16) 0.29868(11) 0.0241(3) Uani 1 1 d . . . . .
H31 H 0.719076 0.105455 0.287449 0.029 Uiso 1 1 calc R U . . .
H32 H 0.683507 -0.010844 0.300525 0.029 Uiso 1 1 calc R U . . .
N4 N 0.64990(5) 0.14775(13) 0.21143(10) 0.0214(2) Uani 1 1 d . . . . .
C5 C 0.60695(6) 0.06224(15) 0.17810(12) 0.0247(3) Uani 1 1 d . . . . .
H51 H 0.615767 -0.034783 0.172471 0.030 Uiso 1 1 calc R U . . .
H52 H 0.585884 0.092874 0.109654 0.030 Uiso 1 1 calc R U . . .
C6 C 0.58113(5) 0.07486(15) 0.25653(11) 0.0220(3) Uani 1 1 d . . . . .
N7 N 0.57632(4) 0.20425(12) 0.28491(9) 0.0182(2) Uani 1 1 d . . . . .
C8 C 0.55774(5) 0.22989(15) 0.35920(11) 0.0188(3) Uani 1 1 d . . . . .
C9 C 0.55671(5) 0.37995(15) 0.38791(11) 0.0195(3) Uani 1 1 d . . . . .
H91 H 0.527062 0.422601 0.342255 0.023 Uiso 1 1 calc R U . . .
H92 H 0.556400 0.386526 0.459571 0.023 Uiso 1 1 calc R U . . .
N10 N 0.59829(4) 0.45677(12) 0.37903(9) 0.0161(2) Uani 1 1 d . . . . .
C11 C 0.63857(5) 0.45829(15) 0.47659(10) 0.0197(3) Uani 1 1 d . . . . .
H111 H 0.626412 0.470200 0.535072 0.024 Uiso 1 1 calc R U . . .
H112 H 0.659828 0.536611 0.476666 0.024 Uiso 1 1 calc R U . . .
C12 C 0.66625(5) 0.32544(16) 0.48929(10) 0.0189(3) Uani 1 1 d . . . . .
C13 C 0.71543(5) 0.08534(16) 0.49427(12) 0.0244(3) Uani 1 1 d . . . . .
H131 H 0.732466 0.002630 0.494759 0.029 Uiso 1 1 calc R U . . .
C14 C 0.71467(6) 0.14431(17) 0.58548(12) 0.0267(3) Uani 1 1 d . . . . .
H141 H 0.731654 0.102479 0.649426 0.032 Uiso 1 1 calc R U . . .
C15 C 0.68917(5) 0.26432(17) 0.58372(11) 0.0242(3) Uani 1 1 d . . . . .
H151 H 0.687463 0.303598 0.645684 0.029 Uiso 1 1 calc R U . . .
C16 C 0.56498(7) -0.03471(17) 0.29939(14) 0.0325(4) Uani 1 1 d . . . . .
H161 H 0.567654 -0.125949 0.277392 0.039 Uiso 1 1 calc R U . . .
C17 C 0.54465(7) -0.00889(19) 0.37564(17) 0.0383(4) Uani 1 1 d . . . . .
H171 H 0.533138 -0.082810 0.406004 0.046 Uiso 1 1 calc R U . . .
C18 C 0.54125(6) 0.12477(17) 0.40711(14) 0.0296(3) Uani 1 1 d . . . . .
H181 H 0.528029 0.144037 0.459895 0.036 Uiso 1 1 calc R U . . .
C20 C 0.66702(6) 0.20054(17) 0.13047(11) 0.0260(3) Uani 1 1 d . . . . .
H201 H 0.639595 0.219260 0.067758 0.031 Uiso 1 1 calc R U . . .
H202 H 0.687424 0.130792 0.113154 0.031 Uiso 1 1 calc R U . . .
C21 C 0.69551(6) 0.33269(17) 0.16613(11) 0.0241(3) Uani 1 1 d . . . . .
O211 O 0.68131(4) 0.41258(11) 0.22338(8) 0.0228(2) Uani 1 1 d . . . . .
O212 O 0.72997(5) 0.35671(15) 0.13682(11) 0.0372(3) Uani 1 1 d . . . . .
C30 C 0.58524(5) 0.59175(14) 0.32905(11) 0.0198(3) Uani 1 1 d . . . . .
H301 H 0.613364 0.653053 0.350184 0.024 Uiso 1 1 calc R U . . .
H302 H 0.560085 0.633932 0.351927 0.024 Uiso 1 1 calc R U . . .
C31 C 0.56725(5) 0.57779(15) 0.21159(11) 0.0197(3) Uani 1 1 d . . . . .
O311 O 0.58227(4) 0.47380(11) 0.17314(7) 0.0206(2) Uani 1 1 d . . . . .
O312 O 0.54087(5) 0.66734(12) 0.15999(9) 0.0312(3) Uani 1 1 d . . . . .
O1W O 0.80345(7) 0.1556(2) 0.15066(16) 0.0397(6) Uani 0.706(4) 1 d . . P A 1
H11W H 0.779234 0.209818 0.139502 0.048 Uiso 0.706(4) 1 d R U P A 1
H12W H 0.801034 0.080718 0.191302 0.048 Uiso 0.706(4) 1 d R U P A 1
O1V O 0.79792(18) 0.2269(6) 0.0881(4) 0.0442(16) Uani 0.294(4) 1 d D . P A 2
H11V H 0.774(2) 0.270(8) 0.102(6) 0.053 Uiso 0.294(4) 1 d D U P A 2
H12V H 0.785(3) 0.212(9) 0.020(2) 0.053 Uiso 0.294(4) 1 d D U P A 2
O2W O 0.46028(4) 0.70340(12) -0.00947(9) 0.0275(2) Uani 1 1 d D . . . .
H21W H 0.4856(7) 0.677(2) 0.0380(15) 0.037(6) Uiso 1 1 d D . . . .
H22W H 0.4533(8) 0.6399(19) -0.0542(15) 0.033(6) Uiso 1 1 d D . . . .
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
O311 Cu1 N1 163.44(5) . . ?
O311 Cu1 O211 92.33(4) . . ?
N1 Cu1 O211 95.11(4) . . ?
O311 Cu1 N7 97.24(5) . . ?
N1 Cu1 N7 83.25(5) . . ?
O211 Cu1 N7 151.06(5) . . ?
O311 Cu1 N10 82.51(4) . . ?
N1 Cu1 N10 81.32(5) . . ?
O211 Cu1 N10 129.23(4) . . ?
N7 Cu1 N10 79.25(4) . . ?
O311 Cu1 N4 118.17(4) . . ?
N1 Cu1 N4 78.03(5) . . ?
O211 Cu1 N4 76.59(5) . . ?
N7 Cu1 N4 74.80(5) . . ?
N10 Cu1 N4 148.40(4) . . ?
C2 N1 C12 121.09(12) . . ?
C2 N1 Cu1 122.10(10) . . ?
C12 N1 Cu1 115.98(10) . . ?
N1 C2 C13 120.80(14) . . ?
N1 C2 C3 117.35(12) . . ?
C13 C2 C3 121.85(13) . . ?
N4 C3 C2 113.68(12) . . ?
N4 C3 H31 108.8 . . ?
C2 C3 H31 108.8 . . ?
N4 C3 H32 108.8 . . ?
C2 C3 H32 108.8 . . ?
H31 C3 H32 107.7 . . ?
C20 N4 C5 116.53(12) . . ?
C20 N4 C3 112.76(12) . . ?
C5 N4 C3 113.53(12) . . ?
C20 N4 Cu1 100.38(9) . . ?
C5 N4 Cu1 105.86(9) . . ?
C3 N4 Cu1 106.02(9) . . ?
N4 C5 C6 108.83(12) . . ?
N4 C5 H51 109.9 . . ?
C6 C5 H51 109.9 . . ?
N4 C5 H52 109.9 . . ?
C6 C5 H52 109.9 . . ?
H51 C5 H52 108.3 . . ?
N7 C6 C16 121.18(15) . . ?
N7 C6 C5 114.16(13) . . ?
C16 C6 C5 124.62(14) . . ?
C8 N7 C6 120.60(13) . . ?
C8 N7 Cu1 114.37(9) . . ?
C6 N7 Cu1 118.17(10) . . ?
N7 C8 C18 121.56(14) . . ?
N7 C8 C9 115.35(12) . . ?
C18 C8 C9 123.08(14) . . ?
N10 C9 C8 112.09(11) . . ?
N10 C9 H91 109.2 . . ?
C8 C9 H91 109.2 . . ?
N10 C9 H92 109.2 . . ?
C8 C9 H92 109.2 . . ?
H91 C9 H92 107.9 . . ?
C30 N10 C11 115.18(11) . . ?
C30 N10 C9 112.86(11) . . ?
C11 N10 C9 112.31(11) . . ?
C30 N10 Cu1 101.19(8) . . ?
C11 N10 Cu1 103.79(8) . . ?
C9 N10 Cu1 110.43(8) . . ?
N10 C11 C12 110.17(11) . . ?
N10 C11 H111 109.6 . . ?
C12 C11 H111 109.6 . . ?
N10 C11 H112 109.6 . . ?
C12 C11 H112 109.6 . . ?
H111 C11 H112 108.1 . . ?
N1 C12 C15 120.86(14) . . ?
N1 C12 C11 115.28(12) . . ?
C15 C12 C11 123.85(13) . . ?
C14 C13 C2 118.50(14) . . ?
C14 C13 H131 120.7 . . ?
C2 C13 H131 120.7 . . ?
C13 C14 C15 120.22(14) . . ?
C13 C14 H141 119.9 . . ?
C15 C14 H141 119.9 . . ?
C12 C15 C14 118.38(14) . . ?
C12 C15 H151 120.8 . . ?
C14 C15 H151 120.8 . . ?
C6 C16 C17 118.63(16) . . ?
C6 C16 H161 120.7 . . ?
C17 C16 H161 120.7 . . ?
C18 C17 C16 119.88(16) . . ?
C18 C17 H171 120.1 . . ?
C16 C17 H171 120.1 . . ?
C17 C18 C8 118.07(16) . . ?
C17 C18 H181 121.0 . . ?
C8 C18 H181 121.0 . . ?
N4 C20 C21 110.26(12) . . ?
N4 C20 H201 109.6 . . ?
C21 C20 H201 109.6 . . ?
N4 C20 H202 109.6 . . ?
C21 C20 H202 109.6 . . ?
H201 C20 H202 108.1 . . ?
O212 C21 O211 124.22(16) . . ?
O212 C21 C20 118.96(15) . . ?
O211 C21 C20 116.82(13) . . ?
C21 O211 Cu1 119.83(10) . . ?
N10 C30 C31 111.08(11) . . ?
N10 C30 H301 109.4 . . ?
C31 C30 H301 109.4 . . ?
N10 C30 H302 109.4 . . ?
C31 C30 H302 109.4 . . ?
H301 C30 H302 108.0 . . ?
O312 C31 O311 124.17(13) . . ?
O312 C31 C30 118.78(13) . . ?
O311 C31 C30 117.02(12) . . ?
C31 O311 Cu1 115.58(9) . . ?
H11W O1W H12W 111.1 . . ?
H11V O1V H12V 102(4) . . ?
H21W O2W H22W 106(2) . . ?
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 O311 1.9430(10) . ?
Cu1 N1 1.9820(11) . ?
Cu1 O211 2.0171(11) . ?
Cu1 N7 2.1511(12) . ?
Cu1 N10 2.1685(11) . ?
Cu1 N4 2.3638(12) . ?
N1 C2 1.3364(18) . ?
N1 C12 1.3462(18) . ?
C2 C13 1.3911(19) . ?
C2 C3 1.516(2) . ?
C3 N4 1.4699(18) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
N4 C20 1.460(2) . ?
N4 C5 1.466(2) . ?
C5 C6 1.519(2) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
C6 N7 1.3401(19) . ?
C6 C16 1.379(2) . ?
N7 C8 1.3339(19) . ?
C8 C18 1.390(2) . ?
C8 C9 1.516(2) . ?
C9 N10 1.4833(17) . ?
C9 H91 0.9900 . ?
C9 H92 0.9900 . ?
N10 C30 1.4747(17) . ?
N10 C11 1.4763(17) . ?
C11 C12 1.512(2) . ?
C11 H111 0.9900 . ?
C11 H112 0.9900 . ?
C12 C15 1.3868(19) . ?
C13 C14 1.386(2) . ?
C13 H131 0.9500 . ?
C14 C15 1.389(2) . ?
C14 H141 0.9500 . ?
C15 H151 0.9500 . ?
C16 C17 1.393(3) . ?
C16 H161 0.9500 . ?
C17 C18 1.385(3) . ?
C17 H171 0.9500 . ?
C18 H181 0.9500 . ?
C20 C21 1.530(2) . ?
C20 H201 0.9900 . ?
C20 H202 0.9900 . ?
C21 O212 1.239(2) . ?
C21 O211 1.2728(19) . ?
C30 C31 1.5313(19) . ?
C30 H301 0.9900 . ?
C30 H302 0.9900 . ?
C31 O312 1.2301(18) . ?
C31 O311 1.2876(17) . ?
O1W H11W 0.8647 . ?
O1W H12W 0.9355 . ?
O1V H11V 0.90(2) . ?
O1V H12V 0.90(2) . ?
O2W H21W 0.859(16) . ?
O2W H22W 0.848(16) . ?
