#------------------------------------------------------------------------------
#$Date: 2019-11-28 21:05:23 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244617 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/92/7239253.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_7239253
loop_
_publ_author_name
'Shankar, Krapa'
'Das, Babulal'
'Baruah, Jubaraj B.'
_publ_section_title
;
 Organic cations controlling the nuclearity of copper(ii)
 2,5-pyridinedicarboxylates
;
_journal_issue                   48
_journal_name_full               'RSC Advances'
_journal_page_first              26220
_journal_paper_doi               10.1039/c3ra44008g
_journal_volume                  3
_journal_year                    2013
_chemical_formula_sum            'C20 H34 Cu N4 O13'
_chemical_formula_weight         602.05
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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
_cell_angle_alpha                107.296(7)
_cell_angle_beta                 108.463(8)
_cell_angle_gamma                97.992(6)
_cell_formula_units_Z            2
_cell_length_a                   8.6201(7)
_cell_length_b                   13.1040(7)
_cell_length_c                   13.3617(13)
_cell_measurement_temperature    296(2)
_cell_volume                     1320.8(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0797
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8992
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.898
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             630
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.093
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.831
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         4660
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.830
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0597
_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)+(0.1501P)²+2.0124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.2132
_reflns_number_gt                3262
_reflns_number_total             4660
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra44008g.txt
_cod_data_source_block           cupdctmda
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1320.79(18)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7239253
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
Cu1 Cu 0.42445(8) 0.81868(5) 0.05487(5) 0.0379(3) Uani 1 1 d .
O1 O 0.3595(5) 0.7381(3) -0.1063(3) 0.0434(9) Uani 1 1 d .
O3 O 0.8815(5) 0.6847(3) 0.3621(3) 0.0475(10) Uani 1 1 d .
O7 O 0.0357(5) 0.9804(3) -0.2518(3) 0.0537(11) Uani 1 1 d .
O5 O 0.5183(5) 0.9105(3) 0.2151(3) 0.0470(10) Uani 1 1 d .
O2 O 0.3957(6) 0.5939(4) -0.2275(3) 0.0603(12) Uani 1 1 d .
N1 N 0.5654(5) 0.7119(3) 0.0704(3) 0.0320(9) Uani 1 1 d .
O4 O 1.0043(5) 0.5778(3) 0.2656(3) 0.0534(11) Uani 1 1 d .
O6 O 0.5308(5) 1.0742(3) 0.3351(3) 0.0493(10) Uani 1 1 d .
O8 O -0.0183(6) 1.1315(3) -0.1562(3) 0.0604(12) Uani 1 1 d .
N3 N 0.9011(5) 0.3470(3) 0.4578(4) 0.0344(10) Uani 1 1 d .
N2 N 0.3333(5) 0.9470(3) 0.0380(3) 0.0334(9) Uani 1 1 d .
O9 O 0.1767(5) 0.7276(3) 0.0584(4) 0.0530(10) Uani 1 1 d D
N4 N 0.1699(6) 1.0036(4) 0.4382(4) 0.0466(12) Uani 1 1 d .
O13 O 0.0523(7) 0.3700(5) 0.1688(5) 0.0906(19) Uani 1 1 d D
O12 O 0.3256(7) 0.3772(5) 0.3686(7) 0.0972(19) Uani 1 1 d D
O11 O 0.6847(7) 0.3330(5) 0.7412(6) 0.0928(19) Uani 1 1 d D
C7 C 0.8978(6) 0.6317(4) 0.2726(4) 0.0350(11) Uani 1 1 d .
C12 C 0.1664(6) 1.0478(4) -0.0527(4) 0.0323(11) Uani 1 1 d .
C5 C 0.7766(6) 0.6339(4) 0.1632(4) 0.0325(11) Uani 1 1 d .
C2 C 0.5553(6) 0.6445(4) -0.0310(4) 0.0363(11) Uani 1 1 d .
C14 C 0.0521(6) 1.0547(4) -0.1627(4) 0.0357(11) Uani 1 1 d .
C6 C 0.6709(6) 0.7058(4) 0.1648(4) 0.0319(11) Uani 1 1 d .
H6 H 0.6742 0.7509 0.2343 0.038 Uiso 1 1 calc R
O10 O 0.4545(9) 0.4163(7) 0.6071(6) 0.107(2) Uani 1 1 d .
C1 C 0.4268(7) 0.6578(4) -0.1322(4) 0.0408(13) Uani 1 1 d .
C9 C 0.3711(6) 1.0265(4) 0.1399(4) 0.0325(11) Uani 1 1 d .
C11 C 0.2037(6) 1.1281(4) 0.0520(4) 0.0365(12) Uani 1 1 d .
H11 H 0.1575 1.1886 0.0568 0.044 Uiso 1 1 calc R
C8 C 0.4828(7) 1.0049(4) 0.2394(4) 0.0395(12) Uani 1 1 d .
C13 C 0.2334(6) 0.9575(4) -0.0558(4) 0.0350(11) Uani 1 1 d .
H13 H 0.2082 0.9022 -0.1254 0.042 Uiso 1 1 calc R
C4 C 0.7672(7) 0.5673(4) 0.0575(4) 0.0381(12) Uani 1 1 d .
H4 H 0.8375 0.5198 0.0529 0.046 Uiso 1 1 calc R
C16 C 0.9786(6) 0.4503(4) 0.4466(4) 0.0364(12) Uani 1 1 d .
H16A H 0.9001 0.4613 0.3827 0.044 Uiso 1 1 calc R
H16B H 1.0807 0.4429 0.4322 0.044 Uiso 1 1 calc R
C10 C 0.3087(7) 1.1190(4) 0.1487(4) 0.0396(12) Uani 1 1 d .
H10 H 0.3373 1.1742 0.2190 0.047 Uiso 1 1 calc R
C20 C 0.2547(7) 0.9154(5) 0.4086(5) 0.0520(15) Uani 1 1 d .
H20A H 0.3256 0.9350 0.3708 0.078 Uiso 1 1 calc R
H20B H 0.1711 0.8473 0.3593 0.078 Uiso 1 1 calc R
H20C H 0.3227 0.9066 0.4763 0.078 Uiso 1 1 calc R
C15 C 0.7308(6) 0.3439(5) 0.4653(5) 0.0434(13) Uani 1 1 d .
H15A H 0.7421 0.4019 0.5331 0.065 Uiso 1 1 calc R
H15B H 0.6851 0.2736 0.4670 0.065 Uiso 1 1 calc R
H15C H 0.6562 0.3542 0.4005 0.065 Uiso 1 1 calc R
C18 C 0.2957(8) 1.1125(5) 0.5005(6) 0.0613(17) Uani 1 1 d .
H18A H 0.3725 1.1125 0.5706 0.092 Uiso 1 1 calc R
H18B H 0.2384 1.1695 0.5159 0.092 Uiso 1 1 calc R
H18C H 0.3579 1.1258 0.4554 0.092 Uiso 1 1 calc R
C3 C 0.6542(7) 0.5710(4) -0.0407(4) 0.0391(12) Uani 1 1 d .
H3 H 0.6453 0.5251 -0.1115 0.047 Uiso 1 1 calc R
C17 C 0.8913(8) 0.2499(4) 0.3596(5) 0.0489(14) Uani 1 1 d .
H17A H 0.8241 0.2559 0.2900 0.073 Uiso 1 1 calc R
H17B H 0.8402 0.1827 0.3648 0.073 Uiso 1 1 calc R
H17C H 1.0032 0.2490 0.3613 0.073 Uiso 1 1 calc R
C19 C 0.0655(8) 0.9703(6) 0.4997(6) 0.0644(18) Uani 1 1 d .
H19A H 0.0128 0.8914 0.4637 0.077 Uiso 1 1 calc R
H19B H 0.1388 0.9849 0.5771 0.077 Uiso 1 1 calc R
H8AA H 0.260(7) 0.730(6) 0.127(3) 0.097 Uiso 1 1 d D
H8AB H 0.125(8) 0.777(5) 0.097(5) 0.097 Uiso 1 1 d D
H9AA H 0.794(5) 0.371(5) 0.751(7) 0.097 Uiso 1 1 d D
H9AB H 0.650(8) 0.398(3) 0.766(7) 0.097 Uiso 1 1 d D
H0BA H 0.455(12) 0.377(7) 0.636(7) 0.097 Uiso 1 1 d D
H0BB H 0.373(11) 0.402(7) 0.543(7) 0.097 Uiso 1 1 d D
H3N H 0.973(7) 0.342(4) 0.519(5) 0.038(15) Uiso 1 1 d .
H4N H 0.098(8) 1.010(5) 0.372(6) 0.065(19) Uiso 1 1 d .
H12A H 0.31(3) 0.319(13) 0.397(19) 0.34(12) Uiso 1 1 d D
H13B H 0.047(10) 0.442(3) 0.206(6) 0.09(3) Uiso 1 1 d D
H13A H -0.03(2) 0.321(15) 0.096(10) 0.41(14) Uiso 1 1 d D
H12B H 0.26(3) 0.382(18) 0.298(9) 0.38(14) 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
O1 Cu1 O5 171.84(17) . .
O1 Cu1 N1 83.24(15) . .
O5 Cu1 N1 95.38(15) . .
O1 Cu1 N2 96.01(15) . .
O5 Cu1 N2 83.35(15) . .
N1 Cu1 N2 165.91(17) . .
O1 Cu1 O9 93.17(16) . .
O5 Cu1 O9 94.98(17) . .
N1 Cu1 O9 101.44(16) . .
N2 Cu1 O9 92.65(15) . .
C1 O1 Cu1 115.8(3) . .
C8 O5 Cu1 115.3(3) . .
C6 N1 C2 119.4(4) . .
C6 N1 Cu1 128.6(3) . .
C2 N1 Cu1 111.9(3) . .
C16 N3 C15 113.8(4) . .
C16 N3 C17 108.3(4) . .
C15 N3 C17 110.9(4) . .
C13 N2 C9 119.7(4) . .
C13 N2 Cu1 128.8(3) . .
C9 N2 Cu1 111.3(3) . .
C20 N4 C18 110.3(4) . .
C20 N4 C19 107.1(5) . .
C18 N4 C19 115.5(5) . .
O4 C7 O3 126.0(5) . .
O4 C7 C5 117.3(5) . .
O3 C7 C5 116.8(4) . .
C11 C12 C13 117.9(4) . .
C11 C12 C14 122.4(4) . .
C13 C12 C14 119.7(4) . .
C4 C5 C6 117.0(4) . .
C4 C5 C7 122.2(4) . .
C6 C5 C7 120.8(4) . .
N1 C2 C3 122.2(5) . .
N1 C2 C1 114.1(4) . .
C3 C2 C1 123.7(5) . .
O8 C14 O7 125.8(5) . .
O8 C14 C12 118.0(4) . .
O7 C14 C12 116.2(4) . .
N1 C6 C5 122.5(4) . .
O2 C1 O1 125.8(5) . .
O2 C1 C2 119.6(5) . .
O1 C1 C2 114.5(4) . .
N2 C9 C10 121.0(5) . .
N2 C9 C8 114.8(4) . .
C10 C9 C8 124.1(4) . .
C10 C11 C12 120.4(4) . .
O6 C8 O5 124.9(5) . .
O6 C8 C9 120.0(5) . .
O5 C8 C9 115.1(4) . .
N2 C13 C12 122.1(4) . .
C3 C4 C5 120.7(4) . .
N3 C16 C16 110.8(5) . 2_766
C11 C10 C9 118.9(5) . .
C2 C3 C4 118.3(5) . .
C19 C19 N4 112.0(7) 2_576 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.946(3) .
Cu1 O5 1.946(4) .
Cu1 N1 1.990(4) .
Cu1 N2 1.994(4) .
Cu1 O9 2.318(4) .
O1 C1 1.282(6) .
O3 C7 1.254(6) .
O7 C14 1.245(6) .
O5 C8 1.287(6) .
O2 C1 1.217(6) .
N1 C6 1.334(6) .
N1 C2 1.348(6) .
O4 C7 1.243(6) .
O6 C8 1.224(6) .
O8 C14 1.241(6) .
N3 C16 1.495(6) .
N3 C15 1.498(7) .
N3 C17 1.501(6) .
N2 C13 1.335(6) .
N2 C9 1.351(6) .
N4 C20 1.474(7) .
N4 C18 1.482(8) .
N4 C19 1.500(8) .
C7 C5 1.516(7) .
C12 C11 1.383(7) .
C12 C13 1.383(7) .
C12 C14 1.525(7) .
C5 C4 1.392(7) .
C5 C6 1.398(6) .
C2 C3 1.376(7) .
C2 C1 1.527(7) .
C9 C10 1.382(7) .
C9 C8 1.505(7) .
C11 C10 1.373(7) .
C4 C3 1.384(7) .
C16 C16 1.516(9) 2_766
C19 C19 1.459(12) 2_576
