#------------------------------------------------------------------------------
#$Date: 2018-09-24 09:49:13 +0300 (Mon, 24 Sep 2018) $
#$Revision: 211137 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/39/1543961.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_1543961
loop_
_publ_author_name
'Fatih Semerci'
'Okan Zafer Yesilel'
'Halis Olmez'
'Orhan Buyukgungor'
_publ_section_title
;
 Supramolecular assemblies of copper(II)-pyridine-2,3-dicarboxylate
 complexes with N-donor ligands and clustered water molecules
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              407
_journal_page_last               417
_journal_paper_doi               10.1016/j.ica.2013.10.006
_journal_volume                  409B
_journal_year                    2014
_chemical_formula_sum            'C10 H15 Cu N3 O5'
_chemical_formula_weight         320.79
_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
_cell_angle_alpha                100.011(5)
_cell_angle_beta                 103.989(4)
_cell_angle_gamma                101.064(5)
_cell_formula_units_Z            2
_cell_length_a                   6.5531(4)
_cell_length_b                   8.1689(5)
_cell_length_c                   12.1297(7)
_cell_measurement_reflns_used    16451
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      1.78
_cell_volume                     601.59(7)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_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  0.0818
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9334
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    1.837
_exptl_absorpt_correction_T_max  0.7602
_exptl_absorpt_correction_T_min  0.3122
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             330
_exptl_crystal_size_max          0.760
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.675
_refine_diff_density_min         -1.234
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2492
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0449P)²+0.1151P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                2230
_reflns_number_total             2492
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2014-409B--407-417-4.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_journal_paper_doi' value
'http://dx.doi.org/10.1016/j.ica.2013.10.006' was changed to
'10.1016/j.ica.2013.10.006'.

Automatic conversion script
Id: cif_fix_values 6433 2018-09-21 13:16:33Z andrius 
;
_cod_original_cell_volume        601.59(6)
_cod_database_code               1543961
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1648(3) 0.1885(3) 0.97603(19) 0.0280(4) Uani 1 1 d . . .
H1 H 0.0802 0.1517 1.0227 0.034 Uiso 1 1 calc R . .
C2 C 0.2820(3) 0.0819(3) 0.9325(2) 0.0310(5) Uani 1 1 d . . .
H2 H 0.2773 -0.0253 0.9493 0.037 Uiso 1 1 calc R . .
C3 C 0.4058(3) 0.1397(3) 0.86356(18) 0.0297(5) Uani 1 1 d . . .
H3 H 0.4885 0.0714 0.8349 0.036 Uiso 1 1 calc R . .
C4 C 0.4093(3) 0.2979(3) 0.83622(16) 0.0244(4) Uani 1 1 d . . .
C5 C 0.2899(3) 0.3992(3) 0.88492(16) 0.0230(4) Uani 1 1 d . . .
C6 C 0.2816(3) 0.5784(3) 0.87095(17) 0.0257(4) Uani 1 1 d . . .
C7 C 0.5328(3) 0.3454(3) 0.75030(18) 0.0281(4) Uani 1 1 d . . .
C8 C 0.1127(4) 0.2009(4) 0.3502(3) 0.0489(7) Uani 1 1 d . . .
H8A H -0.0252 0.1731 0.2904 0.059 Uiso 1 1 calc R . .
H8B H 0.0870 0.1604 0.4174 0.059 Uiso 1 1 calc R . .
C9 C 0.2670(4) 0.1101(4) 0.3044(2) 0.0470(6) Uani 1 1 d . . .
H9A H 0.1997 -0.0118 0.2783 0.056 Uiso 1 1 calc R . .
H9B H 0.2930 0.1515 0.2376 0.056 Uiso 1 1 calc R . .
C10 C 0.4817(5) 0.1379(4) 0.3955(2) 0.0459(6) Uani 1 1 d . . .
H10A H 0.4548 0.1122 0.4666 0.055 Uiso 1 1 calc R . .
H10B H 0.5617 0.0593 0.3677 0.055 Uiso 1 1 calc R . .
N1 N 0.1703(2) 0.3407(3) 0.95290(15) 0.0240(4) Uani 1 1 d . . .
N2 N 0.1990(3) 0.3863(3) 0.3837(2) 0.0416(5) Uani 1 1 d . . .
H2A H 0.1025 0.4311 0.4127 0.050 Uiso 1 1 calc R . .
H2B H 0.1989 0.4215 0.3173 0.050 Uiso 1 1 calc R . .
N3 N 0.6143(3) 0.3142(3) 0.42207(17) 0.0353(5) Uani 1 1 d . . .
H3A H 0.6322 0.3380 0.3548 0.042 Uiso 1 1 calc R . .
H3B H 0.7462 0.3185 0.4682 0.042 Uiso 1 1 calc R . .
O1 O 0.1577(2) 0.6465(2) 0.92147(14) 0.0316(4) Uani 1 1 d . . .
O2 O 0.3940(3) 0.6502(2) 0.81738(15) 0.0357(4) Uani 1 1 d . . .
O3 O 0.4198(2) 0.3347(2) 0.64961(13) 0.0355(4) Uani 1 1 d . . .
O4 O 0.7354(2) 0.3807(3) 0.78595(15) 0.0424(5) Uani 1 1 d . . .
Cu1 Cu 0.0000 0.5000 1.0000 0.03093(13) Uani 1 2 d SU . .
Cu2 Cu 0.5000 0.5000 0.5000 0.03084(13) Uani 1 2 d S . .
O1W O 0.9768(3) 0.2943(4) 0.60857(17) 0.0626(7) Uani 1 1 d D . .
H1W H 1.1104(17) 0.317(6) 0.628(3) 0.094 Uiso 1 1 d D . .
H2W H 0.933(5) 0.306(6) 0.667(2) 0.094 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 C2 121.58(19) . .
N1 C1 H1 119.2 . .
C2 C1 H1 119.2 . .
C3 C2 C1 118.0(2) . .
C3 C2 H2 121.0 . .
C1 C2 H2 121.0 . .
C2 C3 C4 121.11(19) . .
C2 C3 H3 119.4 . .
C4 C3 H3 119.4 . .
C3 C4 C5 117.55(18) . .
C3 C4 C7 117.96(18) . .
C5 C4 C7 124.4(2) . .
N1 C5 C4 120.5(2) . .
N1 C5 C6 113.82(17) . .
C4 C5 C6 125.70(18) . .
O2 C6 O1 124.6(2) . .
O2 C6 C5 120.16(18) . .
O1 C6 C5 115.18(17) . .
O3 C7 O4 126.99(19) . .
O3 C7 C4 115.86(17) . .
O4 C7 C4 117.00(18) . .
N2 C8 C9 111.6(2) . .
N2 C8 H8A 109.3 . .
C9 C8 H8A 109.3 . .
N2 C8 H8B 109.3 . .
C9 C8 H8B 109.3 . .
H8A C8 H8B 108.0 . .
C10 C9 C8 112.6(2) . .
C10 C9 H9A 109.1 . .
C8 C9 H9A 109.1 . .
C10 C9 H9B 109.1 . .
C8 C9 H9B 109.1 . .
H9A C9 H9B 107.8 . .
N3 C10 C9 112.4(2) . .
N3 C10 H10A 109.1 . .
C9 C10 H10A 109.1 . .
N3 C10 H10B 109.1 . .
C9 C10 H10B 109.1 . .
H10A C10 H10B 107.9 . .
C1 N1 C5 121.27(18) . .
C1 N1 Cu1 126.29(14) . .
C5 N1 Cu1 112.32(15) . .
C8 N2 Cu2 122.15(18) . .
C8 N2 H2A 106.8 . .
Cu2 N2 H2A 106.8 . .
C8 N2 H2B 106.8 . .
Cu2 N2 H2B 106.8 . .
H2A N2 H2B 106.6 . .
C10 N3 Cu2 116.84(15) . .
C10 N3 H3A 108.1 . .
Cu2 N3 H3A 108.1 . .
C10 N3 H3B 108.1 . .
Cu2 N3 H3B 108.1 . .
H3A N3 H3B 107.3 . .
C6 O1 Cu1 115.02(14) . .
O1 Cu1 O1 180.000(1) . 2_567
O1 Cu1 N1 83.33(7) . .
O1 Cu1 N1 96.67(7) 2_567 .
O1 Cu1 N1 96.67(7) . 2_567
O1 Cu1 N1 83.33(7) 2_567 2_567
N1 Cu1 N1 180.00(10) . 2_567
N3 Cu2 N3 180.000(1) 2_666 .
N3 Cu2 N2 91.46(8) 2_666 .
N3 Cu2 N2 88.54(8) . .
N3 Cu2 N2 88.54(8) 2_666 2_666
N3 Cu2 N2 91.46(8) . 2_666
N2 Cu2 N2 180.0 . 2_666
H1W O1W H2W 110(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.317(3) .
C1 C2 1.386(3) .
C1 H1 0.9300 .
C2 C3 1.378(3) .
C2 H2 0.9300 .
C3 C4 1.386(3) .
C3 H3 0.9300 .
C4 C5 1.396(3) .
C4 C7 1.523(3) .
C5 N1 1.352(3) .
C5 C6 1.512(3) .
C6 O2 1.228(3) .
C6 O1 1.281(2) .
C7 O3 1.245(3) .
C7 O4 1.251(2) .
C8 N2 1.458(4) .
C8 C9 1.516(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.514(4) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 N3 1.468(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
N1 Cu1 1.9676(17) .
N2 Cu2 2.0590(19) .
N2 H2A 0.9000 .
N2 H2B 0.9000 .
N3 Cu2 2.009(2) .
N3 H3A 0.9000 .
N3 H3B 0.9000 .
O1 Cu1 1.9505(16) .
Cu1 O1 1.9505(16) 2_567
Cu1 N1 1.9676(17) 2_567
Cu2 N3 2.009(2) 2_666
Cu2 N2 2.059(2) 2_666
O1W H1W 0.824(10) .
O1W H2W 0.820(10) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O1W 0.90 2.44 3.043(3) 124.8 2_666
N2 H2B O4 0.90 2.25 3.085(3) 154.0 2_666
N3 H3A O2 0.90 2.07 2.957(3) 166.6 2_666
N3 H3B O1W 0.90 2.05 2.909(3) 159.0 .
O1W H1W O3 0.824(10) 1.954(12) 2.768(2) 169(4) 1_655
O1W H2W O4 0.820(10) 2.246(16) 3.029(3) 160(4) .
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
N1 C1 C2 C3 0.0(3) . . . .
C1 C2 C3 C4 -1.5(3) . . . .
C2 C3 C4 C5 2.5(3) . . . .
C2 C3 C4 C7 -174.28(19) . . . .
C3 C4 C5 N1 -2.2(3) . . . .
C7 C4 C5 N1 174.43(18) . . . .
C3 C4 C5 C6 176.74(18) . . . .
C7 C4 C5 C6 -6.7(3) . . . .
N1 C5 C6 O2 175.42(18) . . . .
C4 C5 C6 O2 -3.6(3) . . . .
N1 C5 C6 O1 -2.4(2) . . . .
C4 C5 C6 O1 178.66(17) . . . .
C3 C4 C7 O3 103.6(2) . . . .
C5 C4 C7 O3 -72.9(3) . . . .
C3 C4 C7 O4 -72.2(3) . . . .
C5 C4 C7 O4 111.2(2) . . . .
N2 C8 C9 C10 62.6(3) . . . .
C8 C9 C10 N3 -70.6(3) . . . .
C2 C1 N1 C5 0.4(3) . . . .
C2 C1 N1 Cu1 176.00(15) . . . .
C4 C5 N1 C1 0.7(3) . . . .
C6 C5 N1 C1 -178.29(18) . . . .
C4 C5 N1 Cu1 -175.42(13) . . . .
C6 C5 N1 Cu1 5.5(2) . . . .
C9 C8 N2 Cu2 -54.5(3) . . . .
C9 C10 N3 Cu2 66.1(2) . . . .
O2 C6 O1 Cu1 -179.82(17) . . . .
C5 C6 O1 Cu1 -2.1(2) . . . .
C6 O1 Cu1 O1 0(100) . . . 2_567
C6 O1 Cu1 N1 4.12(14) . . . .
C6 O1 Cu1 N1 -175.88(14) . . . 2_567
C1 N1 Cu1 O1 178.75(19) . . . .
C5 N1 Cu1 O1 -5.31(13) . . . .
C1 N1 Cu1 O1 -1.25(19) . . . 2_567
C5 N1 Cu1 O1 174.69(13) . . . 2_567
C1 N1 Cu1 N1 -16(100) . . . 2_567
C5 N1 Cu1 N1 160(100) . . . 2_567
C10 N3 Cu2 N3 0(100) . . . 2_666
C10 N3 Cu2 N2 -44.74(18) . . . .
C10 N3 Cu2 N2 135.26(18) . . . 2_666
C8 N2 Cu2 N3 -138.6(2) . . . 2_666
C8 N2 Cu2 N3 41.4(2) . . . .
C8 N2 Cu2 N2 -115(100) . . . 2_666
