#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/24/2232442.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_2232442
loop_
_publ_author_name
'Liu, Dong'
'Li, Ni-Ya'
_publ_section_title
;
 Benzene-1,3-dicarboxylic acid--1,2-bis(4-pyridyl)ethene (1/1)
;
_journal_coeditor_code           RK2306
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3039
_journal_paper_doi               10.1107/S1600536811043418
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H10 N2, C8 H6 O4'
_chemical_formula_moiety         'C12 H10 N2, C8 H6 O4'
_chemical_formula_sum            'C20 H16 N2 O4'
_chemical_formula_weight         348.35
_chemical_name_systematic
;
Benzene-1,3-dicarboxylic acid111,2-bis(4-pyridyl)ethene (1/1)
;
_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                99.47(3)
_cell_angle_beta                 93.87(3)
_cell_angle_gamma                102.69(3)
_cell_formula_units_Z            2
_cell_length_a                   6.8331(14)
_cell_length_b                   6.8804(14)
_cell_length_c                   18.618(4)
_cell_measurement_reflns_used    2779
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.3491
_cell_measurement_theta_min      3.0724
_cell_volume                     837.4(3)
_computing_cell_refinement       'CrystalClear (Rigaku, 2001)'
_computing_data_collection       'CrystalClear (Rigaku, 2001)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_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  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8280
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9666
_exptl_absorpt_correction_T_min  0.9620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.194
_refine_ls_extinction_coef       0.028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0514
_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)+(0.0616P)²+0.1982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1365
_reflns_number_gt                2153
_reflns_number_total             3054
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2306.cif
_cod_data_source_block           I
_cod_database_code               2232442
_cod_database_fobs_code          2232442
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
O O1 -0.1898(3) 0.1743(2) 0.81468(9) 0.0437(5) Uani d . 1 1
H H1 -0.2835 0.1999 0.8378 0.065 Uiso calc R 1 1
O O2 -0.2446(3) -0.0994(3) 0.86694(10) 0.0528(5) Uani d . 1 1
O O3 0.5207(2) 0.0878(2) 0.62885(9) 0.0417(4) Uani d . 1 1
H H3 0.5796 0.1779 0.6079 0.063 Uiso calc R 1 1
O O4 0.4236(3) 0.3460(2) 0.69323(9) 0.0495(5) Uani d . 1 1
N N1 0.5203(3) 0.2721(3) 0.88516(10) 0.0348(5) Uani d . 1 1
N N2 0.6910(3) 0.3812(3) 0.56392(10) 0.0353(5) Uani d . 1 1
C C1 0.0121(3) -0.0583(3) 0.78717(11) 0.0306(5) Uani d . 1 1
C C2 0.1342(3) 0.0735(3) 0.75112(11) 0.0292(5) Uani d . 1 1
H H2 0.1109 0.2030 0.7507 0.035 Uiso calc R 1 1
C C3 0.2909(3) 0.0166(3) 0.71557(11) 0.0283(5) Uani d . 1 1
C C4 0.3240(3) -0.1741(3) 0.71652(11) 0.0346(5) Uani d . 1 1
H H4 0.4293 -0.2141 0.6925 0.041 Uiso calc R 1 1
C C5 0.2028(4) -0.3062(3) 0.75262(12) 0.0403(6) Uani d . 1 1
H H5 0.2260 -0.4357 0.7530 0.048 Uiso calc R 1 1
C C6 0.0478(4) -0.2489(3) 0.78806(12) 0.0369(6) Uani d . 1 1
H H6 -0.0337 -0.3389 0.8128 0.044 Uiso calc R 1 1
C C7 -0.1539(3) 0.0031(3) 0.82700(12) 0.0347(5) Uani d . 1 1
C C8 0.4193(3) 0.1663(3) 0.67866(11) 0.0327(5) Uani d . 1 1
C C9 0.4644(3) 0.4451(4) 0.88158(12) 0.0380(6) Uani d . 1 1
H H9 0.5339 0.5335 0.8533 0.046 Uiso calc R 1 1
C C10 0.3099(3) 0.4988(3) 0.91739(12) 0.0372(6) Uani d . 1 1
H H10 0.2752 0.6216 0.9132 0.045 Uiso calc R 1 1
C C11 0.2046(3) 0.3725(3) 0.95979(11) 0.0334(5) Uani d . 1 1
C C12 0.2643(3) 0.1941(4) 0.96377(12) 0.0390(6) Uani d . 1 1
H H12 0.1989 0.1041 0.9923 0.047 Uiso calc R 1 1
C C13 0.4199(3) 0.1495(4) 0.92569(12) 0.0379(6) Uani d . 1 1
H H13 0.4568 0.0270 0.9284 0.046 Uiso calc R 1 1
C C14 0.0399(3) 0.4214(4) 1.00081(13) 0.0391(6) Uani d . 1 1
H H14 -0.0139 0.3314 1.0313 0.047 Uiso calc R 1 1
C C15 0.7001(3) 0.3777(3) 0.49225(12) 0.0342(5) Uani d . 1 1
H H15 0.6506 0.2538 0.4597 0.041 Uiso calc R 1 1
C C16 0.7789(3) 0.5474(3) 0.46388(12) 0.0332(5) Uani d . 1 1
H H16 0.7805 0.5380 0.4130 0.040 Uiso calc R 1 1
C C17 0.8558(3) 0.7326(3) 0.51039(12) 0.0324(5) Uani d . 1 1
C C18 0.8411(3) 0.7367(4) 0.58473(12) 0.0383(6) Uani d . 1 1
H H18 0.8865 0.8590 0.6184 0.046 Uiso calc R 1 1
C C19 0.7600(3) 0.5615(4) 0.60859(12) 0.0404(6) Uani d . 1 1
H H19 0.7522 0.5677 0.6591 0.049 Uiso calc R 1 1
C C20 0.9500(3) 0.9104(3) 0.48071(12) 0.0353(5) Uani d . 1 1
H H20 0.9390 0.8969 0.4294 0.042 Uiso calc R 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
C7 O1 H1 . 109.5
C8 O3 H3 . 109.5
C13 N1 C9 . 117.51(19)
C15 N2 C19 . 116.9(2)
C2 C1 C6 . 119.4(2)
C2 C1 C7 . 121.13(19)
C6 C1 C7 . 119.4(2)
C1 C2 C3 . 120.74(19)
C1 C2 H2 . 119.6
C3 C2 H2 . 119.6
C4 C3 C2 . 119.2(2)
C4 C3 C8 . 122.45(19)
C2 C3 C8 . 118.30(18)
C5 C4 C3 . 120.3(2)
C5 C4 H4 . 119.9
C3 C4 H4 . 119.9
C6 C5 C4 . 120.3(2)
C6 C5 H5 . 119.9
C4 C5 H5 . 119.9
C5 C6 C1 . 120.1(2)
C5 C6 H6 . 120.0
C1 C6 H6 . 120.0
O2 C7 O1 . 124.3(2)
O2 C7 C1 . 121.9(2)
O1 C7 C1 . 113.81(19)
O4 C8 O3 . 123.6(2)
O4 C8 C3 . 121.53(19)
O3 C8 C3 . 114.84(18)
N1 C9 C10 . 122.7(2)
N1 C9 H9 . 118.6
C10 C9 H9 . 118.6
C9 C10 C11 . 120.2(2)
C9 C10 H10 . 119.9
C11 C10 H10 . 119.9
C10 C11 C12 . 116.8(2)
C10 C11 C14 . 123.4(2)
C12 C11 C14 . 119.8(2)
C13 C12 C11 . 119.7(2)
C13 C12 H12 . 120.2
C11 C12 H12 . 120.2
N1 C13 C12 . 123.1(2)
N1 C13 H13 . 118.5
C12 C13 H13 . 118.5
C14 C14 C11 2_567 126.6(3)
C14 C14 H14 2_567 116.7
C11 C14 H14 . 116.7
N2 C15 C16 . 123.0(2)
N2 C15 H15 . 118.5
C16 C15 H15 . 118.5
C15 C16 C17 . 120.1(2)
C15 C16 H16 . 120.0
C17 C16 H16 . 120.0
C16 C17 C18 . 116.7(2)
C16 C17 C20 . 120.1(2)
C18 C17 C20 . 123.1(2)
C19 C18 C17 . 119.6(2)
C19 C18 H18 . 120.2
C17 C18 H18 . 120.2
N2 C19 C18 . 123.7(2)
N2 C19 H19 . 118.2
C18 C19 H19 . 118.2
C20 C20 C17 2_776 126.3(3)
C20 C20 H20 2_776 116.8
C17 C20 H20 . 116.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C7 . 1.307(3)
O1 H1 . 0.8300
O2 C7 . 1.215(3)
O3 C8 . 1.310(2)
O3 H3 . 0.8300
O4 C8 . 1.215(3)
N1 C13 . 1.333(3)
N1 C9 . 1.338(3)
N2 C15 . 1.336(3)
N2 C19 . 1.343(3)
C1 C2 . 1.383(3)
C1 C6 . 1.387(3)
C1 C7 . 1.495(3)
C2 C3 . 1.390(3)
C2 H2 . 0.9400
C3 C4 . 1.383(3)
C3 C8 . 1.490(3)
C4 C5 . 1.382(3)
C4 H4 . 0.9400
C5 C6 . 1.381(3)
C5 H5 . 0.9400
C6 H6 . 0.9400
C9 C10 . 1.371(3)
C9 H9 . 0.9400
C10 C11 . 1.387(3)
C10 H10 . 0.9400
C11 C12 . 1.387(3)
C11 C14 . 1.470(3)
C12 C13 . 1.378(3)
C12 H12 . 0.9400
C13 H13 . 0.9400
C14 C14 2_567 1.318(5)
C14 H14 . 0.9400
C15 C16 . 1.378(3)
C15 H15 . 0.9400
C16 C17 . 1.390(3)
C16 H16 . 0.9400
C17 C18 . 1.390(3)
C17 C20 . 1.463(3)
C18 C19 . 1.369(3)
C18 H18 . 0.9400
C19 H19 . 0.9400
C20 C20 2_776 1.333(4)
C20 H20 . 0.9400
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
O1 H1 N1 1_455 0.83 1.77 2.597(2) 175.8
O3 H3 N2 . 0.83 1.79 2.618(2) 175.6
