#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/23/8102356.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_8102356
loop_
_publ_author_name
'Lu-Fang Ma'
'Zhao-Lian Yu'
'Xiao-Yi Yang'
_publ_section_title
;
 Crystal structure of 1,3-bi(4-pyridyl)propane -
 5-methylbenzene-1,3-dicarboxylic acid (1:1), C13H14N2 · C9H8O4
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              463
_journal_volume                  223
_journal_year                    2008
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.0650(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8190(11)
_cell_length_b                   11.4122(13)
_cell_length_c                   17.596(2)
_cell_measurement_reflns_used    3353
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      23.27
_cell_measurement_theta_min      2.74
_cell_volume                     1971.4(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13955
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_correction_T_min  0.9580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0597P)²+0.3761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1242
_reflns_number_gt                2683
_reflns_number_total             3657
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2426.cff
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to
'constr' 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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               8102356
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.64316(14) 0.05534(12) 1.10985(7) 0.0634(4) Uani 1 1 d . . .
H1D H 0.6637 0.0848 1.0561 0.095 Uiso 1 1 d R . .
O2 O 0.81074(16) -0.07148(15) 1.09255(9) 0.0877(5) Uani 1 1 d . . .
O3 O 0.40972(16) 0.06825(12) 1.35628(8) 0.0750(4) Uani 1 1 d . . .
O4 O 0.41888(14) -0.08934(12) 1.42953(7) 0.0701(4) Uani 1 1 d . . .
H4D H 0.3436 -0.0386 1.4595 0.105 Uiso 1 1 d R . .
N1 N 1.23925(15) 0.02762(14) 0.50731(8) 0.0572(4) Uani 1 1 d . . .
N2 N 0.70071(16) 0.13315(14) 0.97348(8) 0.0564(4) Uani 1 1 d . . .
C1 C 0.71778(18) -0.03444(16) 1.12998(10) 0.0514(4) Uani 1 1 d . . .
C2 C 0.67835(16) -0.08970(15) 1.20352(9) 0.0448(4) Uani 1 1 d . . .
C3 C 0.72961(17) -0.19946(15) 1.22253(10) 0.0501(4) Uani 1 1 d . . .
H3 H 0.7904 -0.2357 1.1901 0.060 Uiso 1 1 calc R . .
C4 C 0.69248(18) -0.25634(15) 1.28864(10) 0.0511(4) Uani 1 1 d . . .
C5 C 0.60153(17) -0.20047(15) 1.33597(10) 0.0495(4) Uani 1 1 d . . .
H5 H 0.5744 -0.2378 1.3802 0.059 Uiso 1 1 calc R . .
C6 C 0.55015(16) -0.09003(14) 1.31878(9) 0.0442(4) Uani 1 1 d . . .
C7 C 0.58813(16) -0.03465(15) 1.25196(9) 0.0441(4) Uani 1 1 d . . .
H7 H 0.5533 0.0389 1.2398 0.053 Uiso 1 1 calc R . .
C8 C 0.45323(17) -0.02904(15) 1.36989(9) 0.0485(4) Uani 1 1 d . . .
C9 C 0.7474(2) -0.37628(17) 1.30845(13) 0.0698(6) Uani 1 1 d . . .
H9A H 0.7030 -0.4340 1.2770 0.105 Uiso 1 1 calc R . .
H9B H 0.7303 -0.3929 1.3609 0.105 Uiso 1 1 calc R . .
H9C H 0.8437 -0.3782 1.3001 0.105 Uiso 1 1 calc R . .
C10 C 1.1664(2) -0.02432(18) 0.56054(10) 0.0621(5) Uani 1 1 d . . .
H10 H 1.1848 -0.1024 0.5718 0.075 Uiso 1 1 calc R . .
C11 C 1.0655(2) 0.03118(17) 0.59973(10) 0.0595(5) Uani 1 1 d . . .
H11 H 1.0176 -0.0095 0.6364 0.071 Uiso 1 1 calc R . .
C12 C 1.03488(17) 0.14753(16) 0.58481(9) 0.0479(4) Uani 1 1 d . . .
C13 C 1.11155(18) 0.20186(16) 0.52940(9) 0.0528(4) Uani 1 1 d . . .
H13 H 1.0958 0.2801 0.5172 0.063 Uiso 1 1 calc R . .
C14 C 1.21078(18) 0.13985(18) 0.49254(10) 0.0566(5) Uani 1 1 d . . .
H14 H 1.2605 0.1780 0.4555 0.068 Uiso 1 1 calc R . .
C15 C 0.92363(19) 0.21275(17) 0.62504(10) 0.0557(5) Uani 1 1 d . . .
H15A H 0.8400 0.2059 0.5952 0.067 Uiso 1 1 calc R . .
H15B H 0.9476 0.2952 0.6272 0.067 Uiso 1 1 calc R . .
C16 C 0.89710(19) 0.17043(17) 0.70496(10) 0.0562(5) Uani 1 1 d . . .
H16A H 0.8603 0.0916 0.7024 0.067 Uiso 1 1 calc R . .
H16B H 0.9830 0.1668 0.7330 0.067 Uiso 1 1 calc R . .
C17 C 0.8001(2) 0.24695(18) 0.74783(10) 0.0586(5) Uani 1 1 d . . .
H17A H 0.7160 0.2534 0.7183 0.070 Uiso 1 1 calc R . .
H17B H 0.8390 0.3249 0.7519 0.070 Uiso 1 1 calc R . .
C18 C 0.76634(17) 0.20505(14) 0.82664(9) 0.0457(4) Uani 1 1 d . . .
C19 C 0.63831(18) 0.22295(16) 0.85558(10) 0.0519(4) Uani 1 1 d . . .
H19 H 0.5711 0.2593 0.8260 0.062 Uiso 1 1 calc R . .
C20 C 0.61028(19) 0.18698(17) 0.92818(10) 0.0594(5) Uani 1 1 d . . .
H20 H 0.5236 0.2009 0.9466 0.071 Uiso 1 1 calc R . .
C21 C 0.82450(19) 0.11493(16) 0.94551(9) 0.0541(4) Uani 1 1 d . . .
H21 H 0.8889 0.0765 0.9758 0.065 Uiso 1 1 calc R . .
C22 C 0.86117(18) 0.15032(16) 0.87403(9) 0.0516(4) Uani 1 1 d . . .
H22 H 0.9494 0.1376 0.8575 0.062 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'
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
_geom_angle_publ_flag
C1 O1 H1D 112.8 . . ?
C8 O4 H4D 107.3 . . ?
C10 N1 C14 116.85(16) . . ?
C20 N2 C21 116.88(15) . . ?
O2 C1 O1 123.46(17) . . ?
O2 C1 C2 122.18(17) . . ?
O1 C1 C2 114.36(14) . . ?
C3 C2 C7 119.47(15) . . ?
C3 C2 C1 119.33(15) . . ?
C7 C2 C1 121.16(16) . . ?
C4 C3 C2 121.64(16) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 118.07(16) . . ?
C3 C4 C9 121.32(17) . . ?
C5 C4 C9 120.60(17) . . ?
C4 C5 C6 121.43(16) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C7 119.61(15) . . ?
C5 C6 C8 121.64(15) . . ?
C7 C6 C8 118.74(15) . . ?
C2 C7 C6 119.76(16) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
O3 C8 O4 123.15(16) . . ?
O3 C8 C6 122.28(15) . . ?
O4 C8 C6 114.57(15) . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 123.46(18) . . ?
N1 C10 H10 118.3 . . ?
C11 C10 H10 118.3 . . ?
C10 C11 C12 120.21(16) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 116.25(16) . . ?
C11 C12 C15 122.71(15) . . ?
C13 C12 C15 121.04(17) . . ?
C14 C13 C12 119.93(17) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
N1 C14 C13 123.29(16) . . ?
N1 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
C12 C15 C16 114.64(15) . . ?
C12 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
C12 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 C15 113.69(16) . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 C18 115.37(16) . . ?
C16 C17 H17A 108.4 . . ?
C18 C17 H17A 108.4 . . ?
C16 C17 H17B 108.4 . . ?
C18 C17 H17B 108.4 . . ?
H17A C17 H17B 107.5 . . ?
C19 C18 C22 116.79(15) . . ?
C19 C18 C17 120.60(16) . . ?
C22 C18 C17 122.59(15) . . ?
C20 C19 C18 119.88(17) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
N2 C20 C19 123.44(17) . . ?
N2 C20 H20 118.3 . . ?
C19 C20 H20 118.3 . . ?
N2 C21 C22 123.14(17) . . ?
N2 C21 H21 118.4 . . ?
C22 C21 H21 118.4 . . ?
C21 C22 C18 119.85(16) . . ?
C21 C22 H22 120.1 . . ?
C18 C22 H22 120.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.305(2) . ?
O1 H1D 1.0276 . ?
O2 C1 1.212(2) . ?
O3 C8 1.212(2) . ?
O4 C8 1.304(2) . ?
O4 H4D 1.0832 . ?
N1 C10 1.328(2) . ?
N1 C14 1.335(2) . ?
N2 C20 1.332(2) . ?
N2 C21 1.336(2) . ?
C1 C2 1.497(2) . ?
C2 C3 1.389(2) . ?
C2 C7 1.391(2) . ?
C3 C4 1.387(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(2) . ?
C4 C9 1.510(3) . ?
C5 C6 1.389(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.392(2) . ?
C6 C8 1.494(2) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.373(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(2) . ?
C12 C15 1.509(2) . ?
C13 C14 1.376(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.514(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.505(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.510(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.380(2) . ?
C18 C22 1.387(2) . ?
C19 C20 1.374(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.375(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
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
O1 H1D N2 1.03 1.60 2.6298(19) 177.9 .
O4 H4D N1 1.08 1.54 2.618(2) 175.6 1_456
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 -13.3(3) . . . . ?
O1 C1 C2 C3 166.11(15) . . . . ?
O2 C1 C2 C7 168.64(18) . . . . ?
O1 C1 C2 C7 -11.9(2) . . . . ?
C7 C2 C3 C4 0.4(2) . . . . ?
C1 C2 C3 C4 -177.66(16) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C2 C3 C4 C9 179.27(16) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C9 C4 C5 C6 179.87(16) . . . . ?
C4 C5 C6 C7 1.3(3) . . . . ?
C4 C5 C6 C8 -179.42(15) . . . . ?
C3 C2 C7 C6 -0.1(2) . . . . ?
C1 C2 C7 C6 177.96(15) . . . . ?
C5 C6 C7 C2 -0.8(2) . . . . ?
C8 C6 C7 C2 179.94(15) . . . . ?
C5 C6 C8 O3 178.54(18) . . . . ?
C7 C6 C8 O3 -2.2(3) . . . . ?
C5 C6 C8 O4 -2.0(2) . . . . ?
C7 C6 C8 O4 177.26(15) . . . . ?
C14 N1 C10 C11 0.2(3) . . . . ?
N1 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C10 C11 C12 C15 178.98(18) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C15 C12 C13 C14 -178.81(16) . . . . ?
C10 N1 C14 C13 0.0(3) . . . . ?
C12 C13 C14 N1 -0.3(3) . . . . ?
C11 C12 C15 C16 29.4(3) . . . . ?
C13 C12 C15 C16 -151.48(17) . . . . ?
C12 C15 C16 C17 171.93(16) . . . . ?
C15 C16 C17 C18 177.57(16) . . . . ?
C16 C17 C18 C19 -145.61(18) . . . . ?
C16 C17 C18 C22 36.1(3) . . . . ?
C22 C18 C19 C20 0.0(3) . . . . ?
C17 C18 C19 C20 -178.32(17) . . . . ?
C21 N2 C20 C19 0.4(3) . . . . ?
C18 C19 C20 N2 -0.8(3) . . . . ?
C20 N2 C21 C22 0.9(3) . . . . ?
N2 C21 C22 C18 -1.7(3) . . . . ?
C19 C18 C22 C21 1.2(3) . . . . ?
C17 C18 C22 C21 179.48(17) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653950
