#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/81/2228130.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_2228130
loop_
_publ_author_name
'Zhang, Yong-Fang'
'Zhang, Qing-Fu'
'Jin, Juan'
'Sun, De-Zhi'
'Wang, Da-Qi'
_publ_section_title
;
 5-(Pyridin-4-yl)isophthalic acid
;
_journal_coeditor_code           XU5043
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2928
_journal_paper_doi               10.1107/S1600536810039474
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H9 N O4'
_chemical_formula_moiety         'C13 H9 N O4'
_chemical_formula_sum            'C13 H9 N O4'
_chemical_formula_weight         243.21
_chemical_name_systematic
;
5-(Pyridin-4-yl)isophthalic acid
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   15.5362(16)
_cell_length_b                   37.371(3)
_cell_length_c                   7.1716(9)
_cell_measurement_reflns_used    1601
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.52
_cell_measurement_theta_min      2.83
_cell_volume                     4163.9(8)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens SMART 1000 CCD area-detector'
_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  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4224
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.18
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.212
_refine_ls_extinction_coef       0.0010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1004
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0390
_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)+(0.0701P)²+2.9125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1069
_reflns_number_gt                879
_reflns_number_total             1004
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            xu5043.cif
_cod_data_source_block           I
_cod_database_code               2228130
_cod_database_fobs_code          2228130
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
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 0.70913(15) 0.16593(6) 0.0729(5) 0.0455(7) Uani d . 1 . .
O O2 0.81725(15) 0.13320(6) -0.0349(5) 0.0401(7) Uani d . 1 . .
H H2A 0.8354 0.1528 -0.0678 0.060 Uiso calc R 1 . .
O O3 0.45574(15) 0.10618(6) 0.3114(4) 0.0450(8) Uani d . 1 . .
H H3A 0.4068 0.1054 0.3541 0.068 Uiso calc R 1 . .
O O4 0.45297(14) 0.04779(6) 0.3757(4) 0.0451(8) Uani d . 1 . .
N N1 0.85168(17) -0.05737(7) 0.1930(5) 0.0351(7) Uani d . 1 . .
C C1 0.74454(19) 0.13706(8) 0.0469(5) 0.0290(8) Uani d . 1 . .
C C2 0.4902(2) 0.07358(8) 0.3152(6) 0.0294(8) Uani d . 1 . .
C C3 0.70358(19) 0.10312(8) 0.1149(5) 0.0265(7) Uani d . 1 . .
C C4 0.74860(19) 0.07115(8) 0.1188(5) 0.0274(8) Uani d . 1 . .
H H4 0.8058 0.0707 0.0807 0.033 Uiso calc R 1 . .
C C5 0.70940(18) 0.03966(8) 0.1790(5) 0.0257(7) Uani d . 1 . .
C C6 0.62393(19) 0.04072(8) 0.2376(5) 0.0283(8) Uani d . 1 . .
H H6 0.5966 0.0198 0.2755 0.034 Uiso calc R 1 . .
C C7 0.57949(19) 0.07292(8) 0.2395(5) 0.0270(8) Uani d . 1 . .
C C8 0.6192(2) 0.10389(8) 0.1779(5) 0.0268(8) Uani d . 1 . .
H H8 0.5891 0.1254 0.1788 0.032 Uiso calc R 1 . .
C C9 0.7591(2) 0.00577(8) 0.1821(5) 0.0276(8) Uani d . 1 . .
C C10 0.8478(2) 0.00577(8) 0.2122(6) 0.0330(9) Uani d . 1 . .
H H10 0.8772 0.0272 0.2282 0.040 Uiso calc R 1 . .
C C11 0.8915(2) -0.02631(9) 0.2179(6) 0.0374(9) Uani d . 1 . .
H H11 0.9505 -0.0262 0.2399 0.045 Uiso calc R 1 . .
C C12 0.7669(2) -0.05810(9) 0.1627(6) 0.0361(9) Uani d . 1 . .
H H12 0.7397 -0.0800 0.1450 0.043 Uiso calc R 1 . .
C C13 0.7191(2) -0.02726(8) 0.1570(5) 0.0319(8) Uani d . 1 . .
H H13 0.6601 -0.0284 0.1364 0.038 Uiso calc R 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
C1 O2 H2A . . 109.5 ?
C2 O3 H3A . . 109.5 ?
C11 N1 C12 . . 120.0(3) ?
O1 C1 O2 . . 124.4(3) ?
O1 C1 C3 . . 120.3(3) ?
O2 C1 C3 . . 115.3(3) ?
O4 C2 O3 . . 123.1(3) ?
O4 C2 C7 . . 124.4(3) ?
O3 C2 C7 . . 112.5(3) ?
C4 C3 C8 . . 119.3(3) ?
C4 C3 C1 . . 121.4(3) ?
C8 C3 C1 . . 119.3(3) ?
C3 C4 C5 . . 120.9(3) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C6 C5 C4 . . 119.1(3) ?
C6 C5 C9 . . 121.1(3) ?
C4 C5 C9 . . 119.9(3) ?
C7 C6 C5 . . 120.2(3) ?
C7 C6 H6 . . 119.9 ?
C5 C6 H6 . . 119.9 ?
C8 C7 C6 . . 120.0(3) ?
C8 C7 C2 . . 121.2(3) ?
C6 C7 C2 . . 118.8(3) ?
C7 C8 C3 . . 120.6(3) ?
C7 C8 H8 . . 119.7 ?
C3 C8 H8 . . 119.7 ?
C10 C9 C13 . . 117.4(3) ?
C10 C9 C5 . . 121.1(3) ?
C13 C9 C5 . . 121.5(3) ?
C11 C10 C9 . . 119.4(3) ?
C11 C10 H10 . . 120.3 ?
C9 C10 H10 . . 120.3 ?
N1 C11 C10 . . 121.8(3) ?
N1 C11 H11 . . 119.1 ?
C10 C11 H11 . . 119.1 ?
N1 C12 C13 . . 121.5(3) ?
N1 C12 H12 . . 119.3 ?
C13 C12 H12 . . 119.3 ?
C12 C13 C9 . . 119.9(3) ?
C12 C13 H13 . . 120.0 ?
C9 C13 H13 . . 120.0 ?
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 C1 . 1.225(4) ?
O2 C1 . 1.281(4) ?
O2 H2A . 0.8200 ?
O3 C2 . 1.331(4) ?
O3 H3A . 0.8200 ?
O4 C2 . 1.205(4) ?
N1 C11 . 1.327(4) ?
N1 C12 . 1.335(4) ?
C1 C3 . 1.501(4) ?
C2 C7 . 1.489(4) ?
C3 C4 . 1.385(4) ?
C3 C8 . 1.386(4) ?
C4 C5 . 1.394(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.393(4) ?
C5 C9 . 1.483(4) ?
C6 C7 . 1.387(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.384(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.395(4) ?
C9 C13 . 1.394(5) ?
C10 C11 . 1.378(5) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.372(5) ?
C12 H12 . 0.9300 ?
C13 H13 . 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
_geom_hbond_publ_flag
O2 H2A N1 11_654 0.82 1.78 2.558(3) 157 y
O3 H3A O2 9_455 0.82 1.91 2.620(3) 144 y
C10 H10 O1 4_555 0.93 2.57 3.491(4) 172 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656319
