#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/15/2211558.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_2211558
loop_
_publ_author_name
'Ji-Lin Lu'
'Da-Shun Zhang'
'Lin Li'
'Bei-Ping Liu'
_publ_section_title
;
 Bis(dimethylammonium) bis(pyridine-2,5-dicarboxylato)copper(II)
;
_journal_coeditor_code           OB2094
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m3321
_journal_page_last               m3322
_journal_paper_doi               10.1107/S1600536806047180
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '(C2 H8 N)2 [Cu (C7 H3 N O4)2]'
_chemical_formula_moiety         '2C2 H8 N + , C14 H6 Cu N2 O8 2-'
_chemical_formula_sum            'C18 H22 Cu N4 O8'
_chemical_formula_weight         485.94
_chemical_name_systematic
;
Bis(dimethylammonium) bis(pyridine-2,5-dicarboxylato)copper(II)
;
_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                103.232(4)
_cell_angle_beta                 92.484(4)
_cell_angle_gamma                108.439(4)
_cell_formula_units_Z            1
_cell_length_a                   5.2516(13)
_cell_length_b                   8.216(2)
_cell_length_c                   12.290(3)
_cell_measurement_reflns_used    1119
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.81
_cell_volume                     485.8(2)
_computing_cell_refinement       'SAINT (Bruker,1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD area-detector'
_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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2504
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    1.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.655247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             251
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.321
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0372
_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)+(0.0491P)²+0.0557P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0919
_reflns_number_gt                1450
_reflns_number_total             1715
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob2094.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2211558
_cod_database_fobs_code          2211558
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 Cu1 1.0000 1.0000 0.0000 0.0275(2) Uani d S 1
O O1 1.2263(4) 0.8976(3) -0.09590(17) 0.0315(5) Uani d . 1
O O2 1.4979(5) 0.7359(3) -0.09340(18) 0.0402(6) Uani d . 1
O O3 0.9241(4) 0.5701(3) 0.39638(19) 0.0384(6) Uani d . 1
O O4 0.7079(5) 0.7585(3) 0.3789(2) 0.0466(6) Uani d . 1
N N1 1.0489(4) 0.8428(3) 0.09188(19) 0.0221(5) Uani d . 1
C C1 1.3254(6) 0.7966(4) -0.0557(2) 0.0256(6) Uani d . 1
C C2 1.2137(5) 0.7537(4) 0.0504(2) 0.0218(6) Uani d . 1
C C3 1.2705(6) 0.6339(4) 0.1009(2) 0.0270(7) Uani d . 1
H H3 1.3837 0.5729 0.0708 0.032 Uiso calc R 1
C C4 1.1566(6) 0.6056(4) 0.1973(2) 0.0277(7) Uani d . 1
H H4 1.1924 0.5248 0.2324 0.033 Uiso calc R 1
C C5 0.9893(5) 0.6978(4) 0.2412(2) 0.0219(6) Uani d . 1
C C6 0.9386(5) 0.8153(4) 0.1853(2) 0.0233(6) Uani d . 1
H H6 0.8244 0.8769 0.2135 0.028 Uiso calc R 1
C C7 0.8623(6) 0.6727(4) 0.3482(2) 0.0275(7) Uani d . 1
N N2 0.5206(5) 0.2761(3) 0.4280(2) 0.0299(6) Uani d . 1
H H2A 0.4629 0.2766 0.4960 0.036 Uiso calc R 1
H H2B 0.6663 0.3740 0.4362 0.036 Uiso calc R 1
C C8 0.3058(7) 0.2813(5) 0.3497(3) 0.0454(9) Uani d . 1
H H8A 0.3715 0.2902 0.2789 0.068 Uiso calc R 1
H H8B 0.2529 0.3824 0.3806 0.068 Uiso calc R 1
H H8C 0.1526 0.1749 0.3385 0.068 Uiso calc R 1
C C9 0.5987(7) 0.1174(4) 0.3880(3) 0.0432(9) Uani d . 1
H H9A 0.4474 0.0129 0.3850 0.065 Uiso calc R 1
H H9B 0.7465 0.1222 0.4388 0.065 Uiso calc R 1
H H9C 0.6530 0.1139 0.3142 0.065 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O1 2_775 . 180.0 ?
O1 Cu1 N1 2_775 . 96.56(9) ?
O1 Cu1 N1 . . 83.44(9) yes
O1 Cu1 N1 2_775 2_775 83.44(9) ?
O1 Cu1 N1 . 2_775 96.56(9) ?
N1 Cu1 N1 . 2_775 180.0 ?
O1 Cu1 O2 . 1_455 97.55(8) yes
O1 Cu1 O2 . 2_875 82.45(8) no
O2 Cu1 N1 1_455 . 86.99(8) yes
O2 Cu1 N1 2_875 . 93.01(8) no
O1 Cu1 O2 2_775 1_455 82.45(8) no
O2 Cu1 N1 1_455 2_775 93.01(8) no
O2 Cu1 O2 1_455 2_875 180.00 no
O1 Cu1 O2 2_775 2_875 97.55(8) no
O2 Cu1 N1 2_875 2_775 86.99(8) no
C1 O1 Cu1 . . 114.99(18) ?
C6 N1 C2 . . 119.3(2) ?
C6 N1 Cu1 . . 128.35(19) ?
C2 N1 Cu1 . . 112.37(18) ?
O2 C1 O1 . . 126.6(3) ?
O2 C1 C2 . . 119.0(3) ?
O1 C1 C2 . . 114.4(2) ?
N1 C2 C3 . . 121.7(3) ?
N1 C2 C1 . . 114.1(2) ?
C3 C2 C1 . . 124.2(3) ?
C2 C3 C4 . . 119.0(3) ?
C2 C3 H3 . . 120.5 ?
C4 C3 H3 . . 120.5 ?
C5 C4 C3 . . 119.8(3) ?
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
C4 C5 C6 . . 118.2(3) ?
C4 C5 C7 . . 121.6(3) ?
C6 C5 C7 . . 120.2(2) ?
N1 C6 C5 . . 122.1(3) ?
N1 C6 H6 . . 119.0 ?
C5 C6 H6 . . 119.0 ?
O3 C7 O4 . . 126.7(3) ?
O3 C7 C5 . . 116.9(3) ?
O4 C7 C5 . . 116.4(2) ?
C8 N2 C9 . . 111.8(3) ?
C8 N2 H2A . . 109.2 ?
C9 N2 H2A . . 109.2 ?
C8 N2 H2B . . 109.2 ?
C9 N2 H2B . . 109.2 ?
H2A N2 H2B . . 107.9 ?
N2 C8 H8A . . 109.5 ?
N2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
N2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N2 C9 H9A . . 109.5 ?
N2 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
N2 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
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 . 1.965(2) yes
Cu1 N1 2_775 1.965(2) ?
Cu1 O1 2_775 1.952(2) ?
Cu1 O1 . 1.952(2) yes
Cu1 O2 1_455 2.821(2) yes
Cu1 O2 2_875 2.821(2) no
O1 C1 . 1.282(3) ?
O2 C1 . 1.225(3) ?
O3 C7 . 1.246(3) ?
O4 C7 . 1.250(4) ?
N1 C6 . 1.341(3) ?
N1 C2 . 1.347(4) ?
C1 C2 . 1.521(4) ?
C2 C3 . 1.375(4) ?
C3 C4 . 1.383(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.383(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.388(4) ?
C5 C7 . 1.526(4) ?
C6 H6 . 0.9300 ?
N2 C8 . 1.468(4) ?
N2 C9 . 1.474(4) ?
N2 H2A . 0.9000 ?
N2 H2B . 0.9000 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
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
N2 H2B O3 . 0.90 1.92 2.782(3) 158.5
N2 H2A O4 2_666 0.90 1.85 2.737(3) 169.5
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_site_symmetry_1
_geom_torsion
_geom_torsion_publ_flag
O1 Cu1 O1 C1 2_775 -9E1(10) ?
N1 Cu1 O1 C1 . -6.8(2) ?
N1 Cu1 O1 C1 2_775 173.2(2) ?
O1 Cu1 N1 C6 2_775 3.8(3) ?
O1 Cu1 N1 C6 . -176.2(3) ?
N1 Cu1 N1 C6 2_775 -4E1(10) ?
O1 Cu1 N1 C2 2_775 -177.08(19) ?
O1 Cu1 N1 C2 . 2.92(19) ?
N1 Cu1 N1 C2 2_775 14E1(10) ?
O2 Cu1 O1 C1 1_455 -92.9(2) no
O2 Cu1 O1 C1 2_875 87.1(2) no
O2 Cu1 N1 C2 1_455 100.88(19) no
O2 Cu1 N1 C2 2_875 -79.12(19) no
O2 Cu1 N1 C6 1_455 -78.2(2) no
O2 Cu1 N1 C6 2_875 101.8(2) no
Cu1 O1 C1 O2 . -170.3(2) ?
Cu1 O1 C1 C2 . 8.8(3) ?
C6 N1 C2 C3 . 0.5(4) ?
Cu1 N1 C2 C3 . -178.7(2) ?
C6 N1 C2 C1 . 180.0(2) ?
Cu1 N1 C2 C1 . 0.8(3) ?
O2 C1 C2 N1 . 172.8(3) ?
O1 C1 C2 N1 . -6.4(4) ?
O2 C1 C2 C3 . -7.7(4) ?
O1 C1 C2 C3 . 173.1(3) ?
N1 C2 C3 C4 . -0.5(4) ?
C1 C2 C3 C4 . -179.9(3) ?
C2 C3 C4 C5 . -0.2(4) ?
C3 C4 C5 C6 . 0.8(4) ?
C3 C4 C5 C7 . -179.2(3) ?
C2 N1 C6 C5 . 0.2(4) ?
Cu1 N1 C6 C5 . 179.3(2) ?
C4 C5 C6 N1 . -0.9(4) ?
C7 C5 C6 N1 . 179.2(2) ?
C4 C5 C7 O3 . 2.6(4) ?
C6 C5 C7 O3 . -177.5(3) ?
C4 C5 C7 O4 . -178.0(3) ?
C6 C5 C7 O4 . 2.0(4) ?
