#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/17/2011769.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_2011769
loop_
_publ_author_name
'Lin, Jun'
'Zhang, Jun-Yong'
'Xu, Yan'
'Ke, Xiao-Kang'
'Guo, Zijian'
_publ_section_title
;
 N,N'-(1,2-phenylene)bis(pyridine-2-carboxamide) and
 N,N'-(1,2-cyclohexanediyl)bis(pyridine-2-carboxamide)
 toluene hemisolvate
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              192
_journal_page_last               194
_journal_paper_doi               10.1107/S0108270100016395
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C18 H14 N4 O2'
_chemical_formula_sum            'C18 H14 N4 O2'
_chemical_formula_weight         318.33
_chemical_name_systematic
;
N,N'-(1,2-phenylene)bis(pyridine-2-carboxamide)
;
_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'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 95.200(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.346(2)
_cell_length_b                   5.5670(10)
_cell_length_c                   22.578(6)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.44
_cell_measurement_theta_min      4.92
_cell_volume                     1545.4(6)
_computing_cell_refinement       'please provide details'
_computing_data_collection       'please provide details'
_computing_data_reduction        'please provide details'
_computing_molecular_graphics    'please provide details'
_computing_publication_material  'please provide details'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '2θ/ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .078
_diffrn_reflns_av_sigmaI/netI    .077
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            3821
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        5.38
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_refine_diff_density_max         .16
_refine_diff_density_min         -.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          .104
_refine_ls_R_factor_gt           .053
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.048P)²+0.282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .139
_reflns_number_gt                1624
_reflns_number_total             2726
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na1486.cif
_cod_data_source_block           I
_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.

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 '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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2011769
_cod_database_fobs_code          2011769
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_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
_atom_site_type_symbol
N1 .1424(2) .9104(5) .41840(10) .0663(7) Uani d . 1 . . N
N2 .2666(2) .5723(4) .37461(9) .0519(6) Uani d . 1 . . N
H2B .2668 .6217 .4107 .062 Uiso calc R 1 . . H
N3 .3395(2) .2482(4) .46983(8) .0475(6) Uani d . 1 . . N
H3B .3125 .1202 .4839 .057 Uiso calc R 1 . . H
N4 .2551(2) .1948(4) .57402(9) .0573(6) Uani d . 1 . . N
O1 .1829(2) .6341(5) .28131(8) .0814(7) Uani d . 1 . . O
O2 .3731(2) .6428(4) .49015(7) .0623(6) Uani d . 1 . . O
C1 .0860(3) 1.0908(7) .4398(2) .0810(10) Uani d . 1 . . C
H1A .0922 1.1138 .4808 .097 Uiso calc R 1 . . H
C2 .0195(3) 1.2442(7) .4057(2) .0840(10) Uani d . 1 . . C
H2A -.0177 1.3673 .4229 .100 Uiso calc R 1 . . H
C3 .0095(3) 1.2105(7) .3454(2) .0870(10) Uani d . 1 . . C
H3A -.0347 1.3106 .3207 .104 Uiso calc R 1 . . H
C4 .0660(3) 1.0265(6) .32220(10) .0730(10) Uani d . 1 . . C
H4A .0598 .9995 .2814 .087 Uiso calc R 1 . . H
C5 .1315(2) .8821(5) .35920(10) .0527(7) Uani d . 1 . . C
C6 .1961(2) .6858(6) .33440(10) .0545(7) Uani d . 1 . . C
C7 .3394(2) .3848(5) .36520(10) .0448(6) Uani d . 1 . . C
C8 .3767(2) .3474(6) .30950(10) .0550(7) Uani d . 1 . . C
H8A .3565 .4534 .2787 .066 Uiso calc R 1 . . H
C9 .4429(2) .1564(6) .29970(10) .0603(8) Uani d . 1 . . C
H9A .4654 .1323 .2619 .072 Uiso calc R 1 . . H
C10 .4764(2) -.0002(5) .34490(10) .0599(8) Uani d . 1 . . C
H10A .5206 -.1305 .3378 .072 Uiso calc R 1 . . H
C11 .4431(2) .0398(5) .40100(10) .0511(7) Uani d . 1 . . C
H11A .4664 -.0629 .4321 .061 Uiso calc R 1 . . H
C12 .3756(2) .2309(5) .41148(9) .0436(6) Uani d . 1 . . C
C13 .3435(2) .4438(5) .50480(10) .0453(6) Uani d . 1 . . C
C14 .3034(2) .4023(5) .56530(10) .0420(6) Uani d . 1 . . C
C15 .3183(2) .5781(5) .60780(10) .0596(8) Uani d . 1 . . C
H15A .3527 .7214 .5997 .072 Uiso calc R 1 . . H
C16 .2813(3) .5383(6) .66280(10) .0655(9) Uani d . 1 . . C
H16A .2915 .6528 .6928 .079 Uiso calc R 1 . . H
C17 .2296(2) .3282(6) .67220(10) .0605(8) Uani d . 1 . . C
H17A .2024 .2979 .7086 .073 Uiso calc R 1 . . H
C18 .2181(3) .1619(6) .62750(10) .0676(9) Uani d . 1 . . C
H18A .1828 .0185 .6346 .081 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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_publ_flag
C1 N1 C5 116.2(3) yes
C6 N2 C7 128.7(2) yes
C6 N2 H2B 115.7 ?
C7 N2 H2B 115.7 ?
C13 N3 C12 126.7(2) yes
C13 N3 H3B 116.7 ?
C12 N3 H3B 116.7 ?
C14 N4 C18 116.6(2) yes
N1 C1 C2 124.6(3) ?
N1 C1 H1A 117.7 ?
C2 C1 H1A 117.7 ?
C3 C2 C1 118.0(3) ?
C3 C2 H2A 121.0 ?
C1 C2 H2A 121.0 ?
C4 C3 C2 118.7(3) ?
C4 C3 H3A 120.6 ?
C2 C3 H3A 120.6 ?
C3 C4 C5 119.9(3) ?
C3 C4 H4A 120.1 ?
C5 C4 H4A 120.1 ?
N1 C5 C4 122.7(3) ?
N1 C5 C6 116.9(2) ?
C4 C5 C6 120.4(3) ?
O1 C6 N2 124.4(3) yes
O1 C6 C5 120.7(3) yes
N2 C6 C5 115.0(2) ?
C12 C7 C8 118.3(3) ?
C12 C7 N2 120.6(2) ?
C8 C7 N2 121.0(2) ?
C9 C8 C7 120.9(3) ?
C9 C8 H8A 119.6 ?
C7 C8 H8A 119.6 ?
C8 C9 C10 120.9(2) ?
C8 C9 H9A 119.5 ?
C10 C9 H9A 119.5 ?
C9 C10 C11 118.8(3) ?
C9 C10 H10A 120.6 ?
C11 C10 H10A 120.6 ?
C12 C11 C10 120.8(3) ?
C12 C11 H11A 119.6 ?
C10 C11 H11A 119.6 ?
C11 C12 C7 120.1(2) ?
C11 C12 N3 116.8(2) ?
C7 C12 N3 122.9(2) ?
O2 C13 N3 124.9(2) yes
O2 C13 C14 120.9(2) yes
N3 C13 C14 114.2(2) ?
N4 C14 C15 123.5(2) ?
N4 C14 C13 117.2(2) ?
C15 C14 C13 119.3(2) ?
C14 C15 C16 118.8(3) ?
C14 C15 H15A 120.6 ?
C16 C15 H15A 120.6 ?
C17 C16 C15 118.5(3) ?
C17 C16 H16A 120.7 ?
C15 C16 H16A 120.7 ?
C16 C17 C18 119.1(3) ?
C16 C17 H17A 120.4 ?
C18 C17 H17A 120.4 ?
N4 C18 C17 123.4(3) ?
N4 C18 H18A 118.3 ?
C17 C18 H18A 118.3 ?
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
N1 C1 . 1.338(4) yes
N1 C5 . 1.340(3) yes
N2 C6 . 1.356(3) yes
N2 C7 . 1.406(3) yes
N2 H2B . .8600 ?
N3 C13 . 1.343(3) yes
N3 C12 . 1.432(3) yes
N3 H3B . .8600 ?
N4 C14 . 1.324(3) yes
N4 C18 . 1.342(3) yes
O1 C6 . 1.229(3) yes
O2 C13 . 1.222(3) yes
C1 C2 . 1.373(5) ?
C1 H1A . .9300 ?
C2 C3 . 1.368(4) ?
C2 H2A . .9300 ?
C3 C4 . 1.370(5) ?
C3 H3A . .9300 ?
C4 C5 . 1.370(4) ?
C4 H4A . .9300 ?
C5 C6 . 1.491(4) ?
C7 C12 . 1.394(3) ?
C7 C8 . 1.393(3) ?
C8 C9 . 1.372(4) ?
C8 H8A . .9300 ?
C9 C10 . 1.377(4) ?
C9 H9A . .9300 ?
C10 C11 . 1.386(4) ?
C10 H10A . .9300 ?
C11 C12 . 1.384(4) ?
C11 H11A . .9300 ?
C13 C14 . 1.512(3) ?
C14 C15 . 1.371(3) ?
C15 C16 . 1.381(4) ?
C15 H15A . .9300 ?
C16 C17 . 1.358(4) ?
C16 H16A . .9300 ?
C17 C18 . 1.368(4) ?
C17 H17A . .9300 ?
C18 H18A . .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
N2 H2B O2 1_555 .86 2.13 2.840(3) 140 yes
N2 H2B N1 1_555 .86 2.24 2.673(4) 111 yes
N3 H3B N4 1_555 .86 2.25 2.674(3) 110 yes
C8 H8A O1 1_555 .93 2.37 2.898(4) 116 yes
C11 H11A O2 1_545 .93 2.45 3.161(3) 133 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9093083
