#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/99/2019921.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_2019921
loop_
_publ_author_name
'Chen, Xiaocui'
'Wang, Yue'
'Han, Shumin'
'Wei, Yongju'
'Wang, Ruiyao'
_publ_section_title
;
 4,4'-Bipyridine-1,1'-diium acetylenedicarboxylate: a new member of the
 (H₂bipy)[Cu(ox)₂] (bipy is 4,4'-bipyridine and ox is oxalate) family
;
_journal_coeditor_code           EG3178
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229615006336
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C10 H12 N2 2+ , C4 O4 2-'
_chemical_formula_moiety         'C10 H12 N2 2+, C4 O4 2-'
_chemical_formula_sum            'C14 H10 N2 O4'
_chemical_formula_weight         270.24
_chemical_name_systematic
;
4,4'-Bipyridine-1,1'-diium ethynedicarboxylate
;
_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
_audit_creation_method           SHELXL97
_cell_angle_alpha                114.334(3)
_cell_angle_beta                 96.159(3)
_cell_angle_gamma                98.995(3)
_cell_formula_units_Z            1
_cell_length_a                   3.8050(3)
_cell_length_b                   8.6739(7)
_cell_length_c                   9.9138(8)
_cell_measurement_reflns_used    3272
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      4.18
_cell_volume                     289.05(4)
_computing_cell_refinement       'APEX2 (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'APEX2 (Bruker, 2013)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
DIAMOND (Brandenburg, 1999) and
Mercury (Macrae et al, 2006)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
;
Bruker D8 Venture diffractometer with a PHOTON 100 CMOS detector
;
_diffrn_measurement_method       'φ and ω 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  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5593
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         4.18
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_correction_T_min  0.9659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             140
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1291
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0384
_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)+(0.0632P)²+0.0825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                1147
_reflns_number_total             1291
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            eg3178sup1.cif
_cod_data_source_block           I
_cod_database_code               2019921
_cod_database_fobs_code          2019921
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
_atom_site_symmetry_multiplicity
N N1 0.2778(3) 0.38063(13) 0.24637(11) 0.0213(3) Uani d D 1 1
H H1N 0.210(4) 0.4767(14) 0.3075(15) 0.026 Uiso d D 1 1
C C1 0.3057(3) 0.25583(15) 0.28971(13) 0.0238(3) Uani d . 1 1
H H1A 0.2642 0.2713 0.3868 0.029 Uiso calc R 1 1
C C2 0.3942(3) 0.10455(15) 0.19538(13) 0.0227(3) Uani d . 1 1
H H2A 0.4137 0.0166 0.2276 0.027 Uiso calc R 1 1
C C3 0.4546(3) 0.08125(13) 0.05294(12) 0.0173(3) Uani d . 1 1
C C4 0.4219(3) 0.21391(16) 0.01106(14) 0.0242(3) Uani d . 1 1
H H4A 0.4609 0.2026 -0.0853 0.029 Uiso calc R 1 1
C C5 0.3326(4) 0.36181(16) 0.11060(15) 0.0262(3) Uani d . 1 1
H H5A 0.3098 0.4521 0.0817 0.031 Uiso calc R 1 1
C C6 0.0882(3) 0.76011(15) 0.36049(13) 0.0215(3) Uani d . 1 1
C C7 0.0243(3) 0.93075(16) 0.45982(14) 0.0231(3) Uani d . 1 1
O O1 0.1344(3) 0.73297(12) 0.23308(11) 0.0369(3) Uani d . 1 1
O O2 0.0909(3) 0.65538(11) 0.41973(10) 0.0303(3) Uani d . 1 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'
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
C5 N1 C1 . . 120.75(10)
C5 N1 H1N . . 119.3(10)
C1 N1 H1N . . 119.9(10)
N1 C1 C2 . . 120.86(11)
N1 C1 H1A . . 119.6
C2 C1 H1A . . 119.6
C1 C2 C3 . . 119.77(11)
C1 C2 H2A . . 120.1
C3 C2 H2A . . 120.1
C2 C3 C4 . . 117.87(10)
C2 C3 C3 . 2_655 121.36(13)
C4 C3 C3 . 2_655 120.76(12)
C5 C4 C3 . . 119.48(11)
C5 C4 H4A . . 120.3
C3 C4 H4A . . 120.3
N1 C5 C4 . . 121.27(11)
N1 C5 H5A . . 119.4
C4 C5 H5A . . 119.4
O1 C6 O2 . . 126.61(11)
O1 C6 C7 . . 118.78(11)
O2 C6 C7 . . 114.61(10)
C7 C7 C6 2_576 . 179.44(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C5 . 1.3311(16)
N1 C1 . 1.3331(16)
N1 H1N . 0.902(9)
C1 C2 . 1.3799(16)
C1 H1A . 0.9500
C2 C3 . 1.3918(16)
C2 H2A . 0.9500
C3 C4 . 1.3926(16)
C3 C3 2_655 1.489(2)
C4 C5 . 1.3784(16)
C4 H4A . 0.9500
C5 H5A . 0.9500
C6 O1 . 1.2237(15)
C6 O2 . 1.2695(15)
C6 C7 . 1.4773(16)
C7 C7 2_576 1.193(2)
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
C1 H1A O2 2_566 0.95 2.39 3.2612(15) 151.7
C2 H2A O1 1_545 0.95 2.55 3.4030(16) 149.9
C4 H4A O1 2_665 0.95 2.39 3.2363(16) 147.9
C5 H5A O1 . 0.95 2.52 3.1847(15) 127.2
N1 H1N O2 . 0.902(9) 1.659(9) 2.5605(13) 179.1(14)
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_site_symmetry_4
_geom_torsion
C5 N1 C1 C2 . . 0.38(18)
N1 C1 C2 C3 . . -0.11(19)
C1 C2 C3 C4 . . -0.12(18)
C1 C2 C3 C3 . 2_655 -179.10(12)
C2 C3 C4 C5 . . 0.09(18)
C3 C3 C4 C5 2_655 . 179.08(13)
C1 N1 C5 C4 . . -0.41(19)
C3 C4 C5 N1 . . 0.2(2)
O1 C6 C7 C7 . 2_576 -71(18)
O2 C6 C7 C7 . 2_576 109(18)
