#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/81/2228132.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_2228132
loop_
_publ_author_name
'Shen, Fwu Ming'
'Lush, Shie Fu'
_publ_section_title
;
 4-Aminobenzoic acid--4,4'-(propane-1,3-diyl)dipyridine (1/1)
;
_journal_coeditor_code           XU5045
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2748
_journal_paper_doi               10.1107/S1600536810039528
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H14 N2, C7 H7 N O2'
_chemical_formula_moiety         'C13 H14 N2, C7 H7 N O2'
_chemical_formula_sum            'C20 H21 N3 O2'
_chemical_formula_weight         335.40
_chemical_name_systematic
;
4-Aminobenzoic acid--4,4'-(propane-1,3-diyl)dipyridine (1/1)
;
_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                 99.436(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6417(6)
_cell_length_b                   11.1708(9)
_cell_length_c                   20.8775(18)
_cell_measurement_reflns_used    2559
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.53
_cell_measurement_theta_min      2.69
_cell_volume                     1758.1(2)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 1000 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  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9816
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         1.98
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3470
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0443
_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)+(0.0618P)²+0.1063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                2055
_reflns_number_total             3470
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            xu5045.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228132
_cod_database_fobs_code          2228132
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_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 0.2978(2) 0.32540(12) 0.38052(6) 0.0690(4) Uani d . 1 . .
O O2 0.3140(2) 0.13738(12) 0.41752(7) 0.0628(4) Uani d D 1 . .
N N1 -0.0339(3) 0.04320(17) 0.12447(8) 0.0627(5) Uani d D 1 . .
C C1 0.1876(2) 0.24074(15) 0.25210(9) 0.0464(5) Uani d . 1 . .
H H1 0.2285 0.3192 0.2564 0.056 Uiso calc R 1 . .
C C2 0.1117(2) 0.19990(15) 0.19194(9) 0.0470(5) Uani d . 1 . .
H H2 0.1027 0.2507 0.1563 0.056 Uiso calc R 1 . .
C C3 0.0479(2) 0.08273(15) 0.18373(8) 0.0449(4) Uani d . 1 . .
C C4 0.0743(2) 0.00735(15) 0.23811(9) 0.0490(5) Uani d . 1 . .
H H4 0.0405 -0.0726 0.2334 0.059 Uiso calc R 1 . .
C C5 0.1492(2) 0.04932(15) 0.29817(8) 0.0450(4) Uani d . 1 . .
H H5 0.1630 -0.0021 0.3337 0.054 Uiso calc R 1 . .
C C6 0.2049(2) 0.16768(15) 0.30680(8) 0.0422(4) Uani d . 1 . .
C C7 0.2759(3) 0.21774(17) 0.37126(9) 0.0497(5) Uani d . 1 . .
N N2 0.4334(2) 0.23425(14) 0.53122(8) 0.0576(4) Uani d . 1 . .
N N3 0.8995(3) 0.22955(18) 1.01679(8) 0.0715(5) Uani d . 1 . .
C C8 0.4148(3) 0.35141(18) 0.53916(10) 0.0701(6) Uani d . 1 . .
H H8 0.3645 0.3966 0.5034 0.084 Uiso calc R 1 . .
C C9 0.4660(3) 0.40938(18) 0.59730(9) 0.0643(6) Uani d . 1 . .
H H9 0.4518 0.4918 0.5999 0.077 Uiso calc R 1 . .
C C10 0.5383(2) 0.34557(15) 0.65190(8) 0.0433(4) Uani d . 1 . .
C C11 0.5601(3) 0.22429(16) 0.64341(9) 0.0556(5) Uani d . 1 . .
H H11 0.6105 0.1771 0.6783 0.067 Uiso calc R 1 . .
C C12 0.5072(3) 0.17298(18) 0.58325(9) 0.0599(6) Uani d . 1 . .
H H12 0.5241 0.0911 0.5789 0.072 Uiso calc R 1 . .
C C13 0.5864(2) 0.40875(15) 0.71617(8) 0.0480(5) Uani d . 1 . .
H H13A 0.4796 0.4454 0.7268 0.058 Uiso calc R 1 . .
H H13B 0.6680 0.4730 0.7107 0.058 Uiso calc R 1 . .
C C14 0.6693(2) 0.33409(16) 0.77385(8) 0.0467(5) Uani d . 1 . .
H H14A 0.7819 0.3024 0.7659 0.056 Uiso calc R 1 . .
H H14B 0.5922 0.2670 0.7791 0.056 Uiso calc R 1 . .
C C15 0.6987(3) 0.40804(16) 0.83572(8) 0.0506(5) Uani d . 1 . .
H H15A 0.7788 0.4730 0.8299 0.061 Uiso calc R 1 . .
H H15B 0.5862 0.4436 0.8410 0.061 Uiso calc R 1 . .
C C16 0.7721(2) 0.34403(17) 0.89766(9) 0.0482(5) Uani d . 1 . .
C C17 0.7995(3) 0.22242(19) 0.90228(10) 0.0707(6) Uani d . 1 . .
H H17 0.7763 0.1750 0.8653 0.085 Uiso calc R 1 . .
C C18 0.8616(3) 0.1705(2) 0.96176(11) 0.0794(7) Uani d . 1 . .
H H18 0.8776 0.0879 0.9630 0.095 Uiso calc R 1 . .
C C19 0.8731(3) 0.3476(2) 1.01235(10) 0.0758(7) Uani d . 1 . .
H H19 0.8981 0.3926 1.0502 0.091 Uiso calc R 1 . .
C C20 0.8115(3) 0.4068(2) 0.95554(10) 0.0671(6) Uani d . 1 . .
H H20 0.7961 0.4894 0.9559 0.080 Uiso calc R 1 . .
H H1A -0.062(3) 0.0975(14) 0.0954(8) 0.081(8) Uiso d D 1 . .
H H1B -0.094(2) -0.0219(10) 0.1227(10) 0.078(8) Uiso d D 1 . .
H H2A 0.350(3) 0.167(2) 0.4531(6) 0.103(9) Uiso d 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
C7 O2 H2A . . 112.9(18) ?
C3 N1 H1A . . 115.9(15) ?
C3 N1 H1B . . 118.4(15) ?
H1A N1 H1B . . 120(2) ?
C2 C1 C6 . . 121.66(16) ?
C2 C1 H1 . . 119.2 ?
C6 C1 H1 . . 119.2 ?
C1 C2 C3 . . 120.68(17) ?
C1 C2 H2 . . 119.7 ?
C3 C2 H2 . . 119.7 ?
N1 C3 C2 . . 120.86(17) ?
N1 C3 C4 . . 121.59(17) ?
C2 C3 C4 . . 117.54(16) ?
C5 C4 C3 . . 121.20(16) ?
C5 C4 H4 . . 119.4 ?
C3 C4 H4 . . 119.4 ?
C4 C5 C6 . . 121.04(16) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C5 C6 C1 . . 117.71(16) ?
C5 C6 C7 . . 122.47(16) ?
C1 C6 C7 . . 119.81(16) ?
O1 C7 O2 . . 123.08(17) ?
O1 C7 C6 . . 122.41(17) ?
O2 C7 C6 . . 114.51(16) ?
C12 N2 C8 . . 116.41(17) ?
C18 N3 C19 . . 115.21(19) ?
N2 C8 C9 . . 123.57(19) ?
N2 C8 H8 . . 118.2 ?
C9 C8 H8 . . 118.2 ?
C8 C9 C10 . . 120.21(18) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
C11 C10 C9 . . 116.17(17) ?
C11 C10 C13 . . 123.86(17) ?
C9 C10 C13 . . 119.96(16) ?
C12 C11 C10 . . 120.10(18) ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
N2 C12 C11 . . 123.50(18) ?
N2 C12 H12 . . 118.2 ?
C11 C12 H12 . . 118.2 ?
C10 C13 C14 . . 117.31(15) ?
C10 C13 H13A . . 108.0 ?
C14 C13 H13A . . 108.0 ?
C10 C13 H13B . . 108.0 ?
C14 C13 H13B . . 108.0 ?
H13A C13 H13B . . 107.2 ?
C13 C14 C15 . . 111.15(15) ?
C13 C14 H14A . . 109.4 ?
C15 C14 H14A . . 109.4 ?
C13 C14 H14B . . 109.4 ?
C15 C14 H14B . . 109.4 ?
H14A C14 H14B . . 108.0 ?
C16 C15 C14 . . 117.08(16) ?
C16 C15 H15A . . 108.0 ?
C14 C15 H15A . . 108.0 ?
C16 C15 H15B . . 108.0 ?
C14 C15 H15B . . 108.0 ?
H15A C15 H15B . . 107.3 ?
C17 C16 C20 . . 115.43(19) ?
C17 C16 C15 . . 124.14(17) ?
C20 C16 C15 . . 120.40(18) ?
C16 C17 C18 . . 120.2(2) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
N3 C18 C17 . . 124.6(2) ?
N3 C18 H18 . . 117.7 ?
C17 C18 H18 . . 117.7 ?
N3 C19 C20 . . 124.3(2) ?
N3 C19 H19 . . 117.9 ?
C20 C19 H19 . . 117.9 ?
C19 C20 C16 . . 120.3(2) ?
C19 C20 H20 . . 119.9 ?
C16 C20 H20 . . 119.9 ?
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 C7 . 1.225(2) ?
O2 C7 . 1.316(2) ?
O2 H2A . 0.819(15) ?
N1 C3 . 1.365(2) ?
N1 H1A . 0.860(16) ?
N1 H1B . 0.858(13) ?
C1 C2 . 1.372(2) ?
C1 C6 . 1.392(2) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.398(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.401(2) ?
C4 C5 . 1.373(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.392(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.476(2) ?
N2 C12 . 1.329(2) ?
N2 C8 . 1.330(2) ?
N3 C18 . 1.316(3) ?
N3 C19 . 1.335(3) ?
C8 C9 . 1.375(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.381(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.380(2) ?
C10 C13 . 1.507(2) ?
C11 C12 . 1.379(3) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C14 . 1.515(2) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.519(2) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.503(2) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C17 . 1.376(3) ?
C16 C20 . 1.387(3) ?
C17 C18 . 1.382(3) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C19 C20 . 1.373(3) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
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
O2 H2A N2 . 0.819(15) 1.814(15) 2.632(2) 179(3)
N1 H1A N3 1_454 0.860(16) 2.190(16) 3.045(3) 172(2)
N1 H1B O1 2_545 0.858(13) 2.303(14) 3.151(3) 169.7(13)
C13 H13A Cg3 4_566 0.97 2.87 3.6606(17) 139
C14 H14A Cg3 4_666 0.97 2.88 3.6902(17) 142
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656321
