#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:13:32 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180417 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/86/7208641.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_7208641
loop_
_publ_author_name
'Chen, Xiaocui'
'Han, Shumin'
'Wang, Ruiyao'
_publ_section_title
;
 Crystal engineering through charge-assisted hydrogen bonds, multiple
 C--H⋯O bonds and π--π stacking: from (H2bipy)[Cu(ox)2] to
 (H2bipy)[NaH(ox)2] and (H2bipy)[H2(ox)2] (H2bipy =
 4,4′-bipyridin-1,1′-dium; ox = oxalate)
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              6400
_journal_paper_doi               10.1039/c2ce06516a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C14 H11 N2 Na O8'
_chemical_formula_weight         358.24
_chemical_name_systematic
;

?

;
_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           SHELXL-97
_cell_angle_alpha                109.230(3)
_cell_angle_beta                 100.133(3)
_cell_angle_gamma                99.271(3)
_cell_formula_units_Z            1
_cell_length_a                   3.6420(12)
_cell_length_b                   9.706(3)
_cell_length_c                   10.459(3)
_cell_measurement_reflns_used    1284
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      3.65
_cell_volume                     333.96(18)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0283
_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            3346
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.9659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             184
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1310
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0354
_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)+(0.0455P)²+0.1179P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0931
_reflns_number_gt                1097
_reflns_number_total             1310
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce06516a.txt
_cod_data_source_block           compound2
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        333.97(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7208641
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
Na1 Na 0.5000 0.0000 0.0000 0.0215(3) Uani 1 2 d S
O1 O 0.1794(4) 0.13176(13) 0.16053(13) 0.0221(3) Uani 1 1 d .
O2 O 0.4930(4) 0.23357(13) -0.01991(13) 0.0213(3) Uani 1 1 d .
O3 O 0.1994(4) 0.36853(14) 0.28937(13) 0.0240(3) Uani 1 1 d .
O4 O 0.3969(4) 0.45966(13) 0.09106(13) 0.0210(3) Uani 1 1 d D
H4O H 0.446(14) 0.483(6) 0.021(3) 0.025 Uiso 0.50 1 d PD
N1 N 0.1688(4) 0.64647(16) 0.34110(15) 0.0184(3) Uani 1 1 d .
H1A H 0.2074 0.5567 0.3009 0.022 Uiso 1 1 calc R
C1 C 0.2447(5) 0.26955(19) 0.18485(18) 0.0166(4) Uani 1 1 d .
C2 C 0.3932(5) 0.32272(19) 0.07401(17) 0.0161(4) Uani 1 1 d .
C3 C 0.1495(5) 0.69116(19) 0.47468(18) 0.0194(4) Uani 1 1 d .
H3A H 0.1814 0.6266 0.5250 0.023 Uiso 1 1 calc R
C4 C 0.0836(5) 0.82999(19) 0.53979(18) 0.0188(4) Uani 1 1 d .
H4A H 0.0692 0.8609 0.6346 0.023 Uiso 1 1 calc R
C5 C 0.0381(5) 0.92484(18) 0.46636(17) 0.0160(4) Uani 1 1 d .
C6 C 0.0658(5) 0.87499(19) 0.32757(18) 0.0176(4) Uani 1 1 d .
H6A H 0.0396 0.9377 0.2750 0.021 Uiso 1 1 calc R
C7 C 0.1310(5) 0.7349(2) 0.26720(18) 0.0189(4) Uani 1 1 d .
H7A H 0.1493 0.7009 0.1729 0.023 Uiso 1 1 calc R
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'
Na Na 0.0362 0.0249 '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
O2 Na1 O2 180.00(10) 2_655 .
O2 Na1 O1 70.94(4) 2_655 2_655
O2 Na1 O1 109.06(4) . 2_655
O2 Na1 O1 109.06(4) 2_655 .
O2 Na1 O1 70.94(4) . .
O1 Na1 O1 180.00(6) 2_655 .
O2 Na1 O1 94.92(4) 2_655 1_655
O2 Na1 O1 85.08(4) . 1_655
O1 Na1 O1 85.26(5) 2_655 1_655
O1 Na1 O1 94.74(5) . 1_655
O2 Na1 O1 85.08(4) 2_655 2
O2 Na1 O1 94.92(4) . 2
O1 Na1 O1 94.74(5) 2_655 2
O1 Na1 O1 85.26(5) . 2
O1 Na1 O1 180.00(6) 1_655 2
C1 O1 Na1 113.95(11) . .
C1 O1 Na1 110.20(11) . 1_455
Na1 O1 Na1 94.74(5) . 1_455
C2 O2 Na1 114.98(11) . .
C2 O4 H4O 113(3) . .
C7 N1 C3 121.63(15) . .
C7 N1 H1A 119.2 . .
C3 N1 H1A 119.2 . .
O1 C1 O3 126.10(17) . .
O1 C1 C2 116.84(15) . .
O3 C1 C2 117.06(15) . .
O2 C2 O4 126.00(16) . .
O2 C2 C1 119.32(15) . .
O4 C2 C1 114.69(14) . .
N1 C3 C4 120.51(16) . .
N1 C3 H3A 119.7 . .
C4 C3 H3A 119.7 . .
C3 C4 C5 119.77(16) . .
C3 C4 H4A 120.1 . .
C5 C4 H4A 120.1 . .
C4 C5 C6 118.02(16) . .
C4 C5 C5 120.97(19) . 2_576
C6 C5 C5 121.00(19) . 2_576
C7 C6 C5 119.91(16) . .
C7 C6 H6A 120.0 . .
C5 C6 H6A 120.0 . .
N1 C7 C6 120.15(16) . .
N1 C7 H7A 119.9 . .
C6 C7 H7A 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Na1 O2 2.3476(14) 2_655
Na1 O2 2.3476(14) .
Na1 O1 2.3610(13) 2_655
Na1 O1 2.3610(13) .
Na1 O1 2.5849(15) 1_655
Na1 O1 2.5849(15) 2
O1 C1 1.250(2) .
O1 Na1 2.5849(15) 1_455
O2 C2 1.230(2) .
O3 C1 1.252(2) .
O4 C2 1.279(2) .
O4 H4O 0.876(10) .
N1 C7 1.338(2) .
N1 C3 1.338(2) .
N1 H1A 0.8800 .
C1 C2 1.558(3) .
C3 C4 1.376(2) .
C3 H3A 0.9500 .
C4 C5 1.391(3) .
C4 H4A 0.9500 .
C5 C6 1.399(2) .
C5 C5 1.491(3) 2_576
C6 C7 1.377(2) .
C6 H6A 0.9500 .
C7 H7A 0.9500 .
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
N1 H1A O3 0.88 1.79 2.596(2) 152.0 .
N1 H1A O4 0.88 2.36 2.990(2) 128.9 .
O4 H4O O4 0.876(10) 1.602(13) 2.470(2) 171(5) 2_665
C3 H3A O3 0.95 2.90 3.147(2) 96.4 .
C3 H3A O3 0.95 2.57 3.138(2) 118.6 2_566
C4 H4A O1 0.95 2.45 3.359(2) 159.2 2_566
C4 H4A O3 0.95 2.70 3.201(2) 113.6 2_566
C6 H6A O1 0.95 2.58 3.496(2) 163.5 1_565
C7 H7A O4 0.95 2.58 3.112(2) 115.7 .
C7 H7A O2 0.95 2.41 3.208(2) 141.7 2_665
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_4
O2 Na1 O1 C1 162.29(12) 2_655 .
O2 Na1 O1 C1 -17.71(12) . .
O2 Na1 O1 Na1 -83.12(5) 2_655 1_455
O2 Na1 O1 Na1 96.88(5) . 1_455
O1 Na1 O2 C2 -168.09(12) 2_655 .
O1 Na1 O2 C2 11.91(12) . .
O1 Na1 O2 C2 -84.84(12) 1_655 .
O1 Na1 O2 C2 95.16(12) 2 .
Na1 O1 C1 O3 -159.57(15) . .
Na1 O1 C1 O3 95.37(19) 1_455 .
Na1 O1 C1 C2 20.94(19) . .
Na1 O1 C1 C2 -84.12(16) 1_455 .
Na1 O2 C2 O4 174.09(14) . .
Na1 O2 C2 C1 -6.2(2) . .
O1 C1 C2 O2 -10.6(2) . .
O3 C1 C2 O2 169.88(16) . .
O1 C1 C2 O4 169.18(15) . .
O3 C1 C2 O4 -10.4(2) . .
C7 N1 C3 C4 1.0(3) . .
N1 C3 C4 C5 -0.2(3) . .
C3 C4 C5 C6 -0.7(3) . .
C3 C4 C5 C5 179.29(19) . 2_576
C4 C5 C6 C7 0.9(3) . .
C5 C5 C6 C7 -179.11(19) 2_576 .
C3 N1 C7 C6 -0.8(3) . .
C5 C6 C7 N1 -0.1(3) . .
