#------------------------------------------------------------------------------
#$Date: 2018-02-15 09:29:17 +0200 (Thu, 15 Feb 2018) $
#$Revision: 206447 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/10/2021003.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_2021003
loop_
_publ_author_name
'Klongdee, Fatima'
'Boonmak, Jaursup'
'Youngme, Sujittra'
_publ_section_title
;
 Effect of pH on the charge-assisted hydrogen-bonded assembly of the
 anionic [Cu(oxalate)₂]^2{-^} building unit and
 N,N'-ditopic cations
;
_journal_coeditor_code           KU3215
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618002024
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          '(C12 H14 N2) [Cu (C2 O4)2]'
_chemical_formula_moiety         'C12 H14 N2 2+, C4 Cu O8 2-'
_chemical_formula_sum            'C16 H14 Cu N2 O8'
_chemical_formula_weight         425.83
_chemical_name_common
;
4,4'-(Ethane-1,2-diyl)dipyridinium
bis(oxalato-κ²O¹,O²)copper(II)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                109.382(2)
_cell_angle_beta                 95.641(2)
_cell_angle_gamma                97.930(2)
_cell_formula_units_Z            1
_cell_length_a                   3.84860(10)
_cell_length_b                   10.2380(3)
_cell_length_c                   10.6080(4)
_cell_measurement_reflns_used    5637
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.216
_cell_measurement_theta_min      3.4565
_cell_volume                     385.85(2)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
SHELXL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker D8 QUEST PHOTON 100
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11134
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.924
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.470
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_description       block
_exptl_crystal_F_000             217
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.359
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1515
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0423P)²+0.2752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0866
_reflns_number_gt                1370
_reflns_number_total             1515
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ku3215sup1.cif
_cod_data_source_block           compoundII
_cod_database_code               2021003
_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   0.351
_shelx_estimated_absorpt_t_max   0.957
loop_
_space_group_symop_operation_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_occupancy
Cu Cu1 0.0000 0.5000 0.0000 0.02811(17) Uani d 1
O O1 0.0783(5) 0.68107(18) 0.14009(17) 0.0323(4) Uani d 1
O O2 0.3594(5) 0.78730(19) 0.35205(18) 0.0358(4) Uani d 1
O O3 0.3273(5) 0.45021(18) 0.12059(17) 0.0338(4) Uani d 1
O O4 0.6076(5) 0.54334(19) 0.33262(18) 0.0355(4) Uani d 1
N N1 -0.1332(5) 0.7665(2) 0.5689(2) 0.0281(5) Uani d 1
H H1 -0.2503 0.7127 0.4888 0.034 Uiso calc 1
C C1 0.2779(6) 0.6865(2) 0.2468(2) 0.0245(5) Uani d 1
C C2 0.4187(6) 0.5490(3) 0.2350(2) 0.0263(5) Uani d 1
C C3 0.0221(7) 0.7072(3) 0.6474(3) 0.0303(6) Uani d 1
H H3 0.0060 0.6078 0.6165 0.036 Uiso calc 1
C C4 0.2072(7) 0.7888(3) 0.7739(3) 0.0284(5) Uani d 1
H H4 0.3163 0.7460 0.8303 0.034 Uiso calc 1
C C5 0.2320(6) 0.9337(3) 0.8176(2) 0.0234(5) Uani d 1
C C6 0.0655(6) 0.9909(3) 0.7315(3) 0.0273(5) Uani d 1
H H6 0.0786 1.0899 0.7587 0.033 Uiso calc 1
C C7 -0.1169(6) 0.9054(3) 0.6079(2) 0.0286(5) Uani d 1
H H7 -0.2321 0.9449 0.5497 0.034 Uiso calc 1
C C8 0.4292(6) 1.0343(3) 0.9522(2) 0.0260(5) Uani d 1
H H8A 0.2683 1.0964 0.9971 0.031 Uiso calc 1
H H8B 0.6310 1.0946 0.9358 0.031 Uiso calc 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_565 . 180.00(11) yes
O1 Cu1 O3 2_565 2_565 85.73(7) yes
O1 Cu1 O3 . 2_565 94.27(7) yes
O1 Cu1 O3 2_565 . 94.27(7) yes
O1 Cu1 O3 . . 85.73(7) yes
O3 Cu1 O3 2_565 . 180.0 yes
C1 O1 Cu1 . . 112.67(15) no
C2 O3 Cu1 . . 111.56(15) no
C3 N1 C7 . . 121.9(2) no
C3 N1 H1 . . 119.1 no
C7 N1 H1 . . 119.1 no
O2 C1 O1 . . 126.1(2) no
O2 C1 C2 . . 119.5(2) no
O1 C1 C2 . . 114.4(2) no
O4 C2 O3 . . 125.5(2) no
O4 C2 C1 . . 119.2(2) no
O3 C2 C1 . . 115.4(2) no
N1 C3 C4 . . 120.4(2) no
N1 C3 H3 . . 119.8 no
C4 C3 H3 . . 119.8 no
C3 C4 C5 . . 119.4(2) no
C3 C4 H4 . . 120.3 no
C5 C4 H4 . . 120.3 no
C4 C5 C6 . . 118.0(2) no
C4 C5 C8 . . 124.6(2) no
C6 C5 C8 . . 117.4(2) no
C7 C6 C5 . . 120.3(2) no
C7 C6 H6 . . 119.8 no
C5 C6 H6 . . 119.8 no
N1 C7 C6 . . 120.0(2) no
N1 C7 H7 . . 120.0 no
C6 C7 H7 . . 120.0 no
C5 C8 C8 . 2_677 115.2(3) no
C5 C8 H8A . . 108.5 no
C8 C8 H8A 2_677 . 108.5 no
C5 C8 H8B . . 108.5 no
C8 C8 H8B 2_677 . 108.5 no
H8A C8 H8B . . 107.5 no
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 O1 2_565 1.9145(16) yes
Cu1 O1 . 1.9145(16) yes
Cu1 O3 2_565 1.9431(17) yes
Cu1 O3 . 1.9432(17) yes
O1 C1 . 1.285(3) no
O2 C1 . 1.220(3) no
O3 C2 . 1.274(3) no
O4 C2 . 1.228(3) no
N1 C3 . 1.326(3) no
N1 C7 . 1.333(3) no
N1 H1 . 0.8800 no
C1 C2 . 1.548(3) no
C3 C4 . 1.382(4) no
C3 H3 . 0.9500 no
C4 C5 . 1.386(4) no
C4 H4 . 0.9500 no
C5 C6 . 1.390(3) no
C5 C8 . 1.506(3) no
C6 C7 . 1.366(4) no
C6 H6 . 0.9500 no
C7 H7 . 0.9500 no
C8 C8 2_677 1.513(5) no
C8 H8A . 0.9900 no
C8 H8B . 0.9900 no
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
N1 H1 O2 1_455 0.88 2.36 2.951(3) 125 yes
N1 H1 O4 1_455 0.88 1.92 2.753(3) 156 yes
C3 H3 O4 2_666 0.95 2.43 3.157(4) 133 yes
C6 H6 O1 2_576 0.95 2.42 3.326(4) 159 yes

_cod_database_fobs_code 2021003
