#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/06/2220621.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_2220621
loop_
_publ_author_name
'Huang, Qun-Zeng'
'Shi, Heng-Zhen'
_publ_section_title
;
 1,2-Di-2-pyridylethylene--phenylsuccinic acid (1/1)
;
_journal_coeditor_code           SI2134
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o182
_journal_paper_doi               10.1107/S1600536808040245
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H10 O4, C12 H10 N2'
_chemical_formula_moiety         'C10 H10 O4, C12 H10 N2'
_chemical_formula_sum            'C22 H20 N2 O4'
_chemical_formula_weight         376.40
_chemical_name_systematic
;
1,2-Di-2-pyridylethylene--phenylsuccinic acid (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           SHELXL-97
_cell_angle_alpha                80.801(2)
_cell_angle_beta                 69.696(2)
_cell_angle_gamma                77.663(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6707(13)
_cell_length_b                   10.9714(17)
_cell_length_c                   11.2013(17)
_cell_measurement_reflns_used    1614
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      2.54
_cell_volume                     972.0(3)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART 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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7261
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.54
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9745
_exptl_absorpt_correction_T_min  0.9569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.195
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0469
_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)+(0.0553P)²+0.1924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1332
_reflns_number_gt                2369
_reflns_number_total             3605
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            si2134.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               2220621
_cod_database_fobs_code          2220621
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_disorder_assembly
_atom_site_disorder_group
O O1 0.47679(18) 0.96437(13) -0.17709(14) 0.0637(5) Uani d . 1 . .
H H1 0.5453 0.9815 -0.2464 0.096 Uiso calc R 1 . .
O O2 0.6712(2) 0.79683(17) -0.17226(16) 0.0896(7) Uani d . 1 . .
O O3 0.27415(18) 0.75636(14) 0.27577(13) 0.0620(4) Uani d . 1 . .
O O4 0.45071(18) 0.57475(13) 0.26650(13) 0.0618(4) Uani d . 1 . .
H H4 0.3867 0.5601 0.3387 0.093 Uiso calc R 1 . .
N N1 0.2501(2) 0.51408(15) 0.50443(15) 0.0485(4) Uani d . 1 . .
N N2 0.66326(19) 0.01005(14) 0.57849(15) 0.0454(4) Uani d . 1 . .
C C1 0.1106(3) 0.5966(2) 0.5536(2) 0.0546(6) Uani d . 1 . .
H H1A 0.0995 0.6764 0.5110 0.065 Uiso calc R 1 . .
C C2 -0.0168(3) 0.5695(2) 0.6635(2) 0.0567(6) Uani d . 1 . .
H H2 -0.1108 0.6295 0.6947 0.068 Uiso calc R 1 . .
C C3 -0.0007(3) 0.4507(2) 0.7260(2) 0.0561(6) Uani d . 1 . .
H H3 -0.0845 0.4289 0.7999 0.067 Uiso calc R 1 . .
C C4 0.1410(3) 0.3649(2) 0.6774(2) 0.0531(5) Uani d . 1 . .
H H4A 0.1531 0.2846 0.7187 0.064 Uiso calc R 1 . .
C C5 0.2663(2) 0.39814(18) 0.56644(18) 0.0434(5) Uani d . 1 . .
C C6 0.4216(3) 0.31193(19) 0.5089(2) 0.0503(5) Uani d . 1 . .
H H6 0.4894 0.3386 0.4284 0.060 Uiso calc R 1 . .
C C7 0.4745(2) 0.20028(18) 0.56004(19) 0.0470(5) Uani d . 1 . .
H H7 0.4071 0.1742 0.6409 0.056 Uiso calc R 1 . .
C C8 0.6279(2) 0.11358(18) 0.50279(18) 0.0440(5) Uani d . 1 . .
C C9 0.7339(3) 0.1334(2) 0.3775(2) 0.0657(7) Uani d . 1 . .
H H9 0.7090 0.2046 0.3256 0.079 Uiso calc R 1 . .
C C10 0.8761(3) 0.0464(2) 0.3313(2) 0.0720(7) Uani d . 1 . .
H H10 0.9480 0.0595 0.2485 0.086 Uiso calc R 1 . .
C C11 0.9108(3) -0.0587(2) 0.4075(2) 0.0624(6) Uani d . 1 . .
H H11 1.0050 -0.1187 0.3775 0.075 Uiso calc R 1 . .
C C12 0.8017(3) -0.07322(19) 0.5304(2) 0.0549(6) Uani d . 1 . .
H H12 0.8252 -0.1445 0.5827 0.066 Uiso calc R 1 . .
C C13 0.5369(2) 0.85814(19) -0.12306(19) 0.0462(5) Uani d . 1 . .
C C14 0.4165(2) 0.81888(18) 0.00741(18) 0.0427(5) Uani d . 1 . .
H H14 0.3682 0.8931 0.0550 0.051 Uiso calc R 1 . .
C C15 0.2750(2) 0.77139(17) -0.01329(17) 0.0399(5) Uani d . 1 . .
C C16 0.1120(2) 0.83595(19) 0.02700(19) 0.0488(5) Uani d . 1 . .
H H16 0.0881 0.9074 0.0694 0.059 Uiso calc R 1 . .
C C17 -0.0154(3) 0.7948(2) 0.0046(2) 0.0588(6) Uani d . 1 . .
H H17 -0.1236 0.8394 0.0316 0.071 Uiso calc R 1 . .
C C18 0.0169(3) 0.6883(2) -0.0573(2) 0.0635(6) Uani d . 1 . .
H H18 -0.0688 0.6612 -0.0723 0.076 Uiso calc R 1 . .
C C19 0.1789(3) 0.6220(2) -0.0970(2) 0.0603(6) Uani d . 1 . .
H H19 0.2018 0.5498 -0.1381 0.072 Uiso calc R 1 . .
C C20 0.3064(3) 0.66335(19) -0.07542(19) 0.0497(5) Uani d . 1 . .
H H20 0.4145 0.6186 -0.1026 0.060 Uiso calc R 1 . .
C C21 0.5086(2) 0.7212(2) 0.08432(18) 0.0501(5) Uani d . 1 . .
H H21A 0.5541 0.6462 0.0396 0.060 Uiso calc R 1 . .
H H21B 0.6013 0.7538 0.0899 0.060 Uiso calc R 1 . .
C C22 0.3968(2) 0.68718(19) 0.21791(18) 0.0438(5) Uani d . 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
_geom_angle_publ_flag
C13 O1 H1 . . 109.5 ?
C22 O4 H4 . . 109.5 ?
C1 N1 C5 . . 118.17(17) ?
C12 N2 C8 . . 118.53(17) ?
N1 C1 C2 . . 123.70(19) ?
N1 C1 H1A . . 118.1 ?
C2 C1 H1A . . 118.1 ?
C1 C2 C3 . . 118.01(19) ?
C1 C2 H2 . . 121.0 ?
C3 C2 H2 . . 121.0 ?
C4 C3 C2 . . 119.24(19) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C3 C4 C5 . . 120.13(19) ?
C3 C4 H4A . . 119.9 ?
C5 C4 H4A . . 119.9 ?
N1 C5 C4 . . 120.74(17) ?
N1 C5 C6 . . 115.87(17) ?
C4 C5 C6 . . 123.39(18) ?
C7 C6 C5 . . 126.66(19) ?
C7 C6 H6 . . 116.7 ?
C5 C6 H6 . . 116.7 ?
C6 C7 C8 . . 126.93(19) ?
C6 C7 H7 . . 116.5 ?
C8 C7 H7 . . 116.5 ?
N2 C8 C9 . . 120.45(18) ?
N2 C8 C7 . . 116.06(17) ?
C9 C8 C7 . . 123.49(18) ?
C10 C9 C8 . . 119.6(2) ?
C10 C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C11 C10 C9 . . 119.9(2) ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C10 C11 C12 . . 118.0(2) ?
C10 C11 H11 . . 121.0 ?
C12 C11 H11 . . 121.0 ?
N2 C12 C11 . . 123.6(2) ?
N2 C12 H12 . . 118.2 ?
C11 C12 H12 . . 118.2 ?
O2 C13 O1 . . 123.53(18) ?
O2 C13 C14 . . 123.50(18) ?
O1 C13 C14 . . 112.95(16) ?
C15 C14 C13 . . 108.73(16) ?
C15 C14 C21 . . 112.41(16) ?
C13 C14 C21 . . 110.86(15) ?
C15 C14 H14 . . 108.2 ?
C13 C14 H14 . . 108.2 ?
C21 C14 H14 . . 108.2 ?
C16 C15 C20 . . 118.20(19) ?
C16 C15 C14 . . 120.81(18) ?
C20 C15 C14 . . 120.98(17) ?
C17 C16 C15 . . 120.7(2) ?
C17 C16 H16 . . 119.6 ?
C15 C16 H16 . . 119.6 ?
C18 C17 C16 . . 120.7(2) ?
C18 C17 H17 . . 119.7 ?
C16 C17 H17 . . 119.7 ?
C17 C18 C19 . . 119.3(2) ?
C17 C18 H18 . . 120.4 ?
C19 C18 H18 . . 120.4 ?
C20 C19 C18 . . 120.1(2) ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C19 C20 C15 . . 121.01(19) ?
C19 C20 H20 . . 119.5 ?
C15 C20 H20 . . 119.5 ?
C22 C21 C14 . . 112.58(16) ?
C22 C21 H21A . . 109.1 ?
C14 C21 H21A . . 109.1 ?
C22 C21 H21B . . 109.1 ?
C14 C21 H21B . . 109.1 ?
H21A C21 H21B . . 107.8 ?
O3 C22 O4 . . 123.46(18) ?
O3 C22 C21 . . 123.82(18) ?
O4 C22 C21 . . 112.68(16) ?
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
O1 C13 . 1.315(2) ?
O1 H1 . 0.8200 ?
O2 C13 . 1.204(2) ?
O3 C22 . 1.209(2) ?
O4 C22 . 1.324(2) ?
O4 H4 . 0.8200 ?
N1 C1 . 1.347(2) ?
N1 C5 . 1.352(2) ?
N2 C12 . 1.344(2) ?
N2 C8 . 1.352(2) ?
C1 C2 . 1.380(3) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.381(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.378(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.395(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.474(3) ?
C6 C7 . 1.326(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.465(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.398(3) ?
C9 C10 . 1.382(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.365(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.380(3) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C14 . 1.531(3) ?
C14 C15 . 1.529(3) ?
C14 C21 . 1.532(3) ?
C14 H14 . 0.9800 ?
C15 C16 . 1.391(3) ?
C15 C20 . 1.399(3) ?
C16 C17 . 1.389(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.383(3) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.390(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.387(3) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
C21 C22 . 1.513(3) ?
C21 H21A . 0.9700 ?
C21 H21B . 0.9700 ?
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
O4 H4 N1 . 0.82 1.88 2.699(2) 176 y
O1 H1 N2 1_564 0.82 1.88 2.683(2) 165 y
C2 H2 O2 1_456 0.93 2.56 3.472(3) 164 y
C11 H11 O3 1_645 0.93 2.43 3.350(3) 170 y
C3 H3 Cg1 2_566 0.93 2.86 3.650(4) 143 y
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . -0.1(3) ?
N1 C1 C2 C3 . . . . -0.5(3) ?
C1 C2 C3 C4 . . . . 0.6(3) ?
C2 C3 C4 C5 . . . . 0.0(3) ?
C1 N1 C5 C4 . . . . 0.7(3) ?
C1 N1 C5 C6 . . . . -179.70(18) ?
C3 C4 C5 N1 . . . . -0.6(3) ?
C3 C4 C5 C6 . . . . 179.8(2) ?
N1 C5 C6 C7 . . . . 171.0(2) ?
C4 C5 C6 C7 . . . . -9.4(3) ?
C5 C6 C7 C8 . . . . 179.33(19) ?
C12 N2 C8 C9 . . . . -0.3(3) ?
C12 N2 C8 C7 . . . . 179.38(18) ?
C6 C7 C8 N2 . . . . 173.9(2) ?
C6 C7 C8 C9 . . . . -6.4(4) ?
N2 C8 C9 C10 . . . . -0.2(3) ?
C7 C8 C9 C10 . . . . -179.9(2) ?
C8 C9 C10 C11 . . . . 0.9(4) ?
C9 C10 C11 C12 . . . . -0.9(4) ?
C8 N2 C12 C11 . . . . 0.3(3) ?
C10 C11 C12 N2 . . . . 0.4(4) ?
O2 C13 C14 C15 . . . . -104.5(2) ?
O1 C13 C14 C15 . . . . 74.0(2) ?
O2 C13 C14 C21 . . . . 19.5(3) ?
O1 C13 C14 C21 . . . . -161.95(18) ?
C13 C14 C15 C16 . . . . -114.07(19) ?
C21 C14 C15 C16 . . . . 122.80(19) ?
C13 C14 C15 C20 . . . . 64.7(2) ?
C21 C14 C15 C20 . . . . -58.5(2) ?
C20 C15 C16 C17 . . . . -0.8(3) ?
C14 C15 C16 C17 . . . . 178.00(17) ?
C15 C16 C17 C18 . . . . 0.5(3) ?
C16 C17 C18 C19 . . . . 0.2(3) ?
C17 C18 C19 C20 . . . . -0.5(3) ?
C18 C19 C20 C15 . . . . 0.3(3) ?
C16 C15 C20 C19 . . . . 0.4(3) ?
C14 C15 C20 C19 . . . . -178.39(18) ?
C15 C14 C21 C22 . . . . -62.5(2) ?
C13 C14 C21 C22 . . . . 175.58(17) ?
C14 C21 C22 O3 . . . . -26.4(3) ?
C14 C21 C22 O4 . . . . 155.70(18) ?
