#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:52:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180100 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/46/7054656.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_7054656
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Wijethunga, Tharanga K.'
'Desper, John'
_publ_section_title
;
 Molecular electrostatic potential dependent selectivity of hydrogen
 bonding
;
_journal_issue                   2
_journal_name_full               'New J. Chem.'
_journal_page_first              822
_journal_paper_doi               10.1039/C4NJ01324G
_journal_volume                  39
_journal_year                    2015
_chemical_formula_moiety
;
(C18 H16 N6) (C7 H12 O4)2
;
_chemical_formula_sum            'C32 H40 N6 O8'
_chemical_formula_weight         636.70
_chemical_name_systematic
;
TW-2B-8-C 1,1'-di[(2-pyridyl)methyl]-2,2'-biimidazole, [HOOC-(CH2)5-COOH]2
;
_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                87.266(11)
_cell_angle_beta                 88.665(10)
_cell_angle_gamma                72.608(9)
_cell_formula_units_Z            1
_cell_length_a                   4.9161(10)
_cell_length_b                   8.0077(16)
_cell_length_c                   20.828(4)
_cell_measurement_reflns_used    3857
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      23.38
_cell_measurement_theta_min      2.88
_cell_volume                     781.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Bruker APEX-II 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  0.0949
_diffrn_reflns_av_sigmaI/netI    0.1045
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21382
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         31.05
_diffrn_reflns_theta_min         0.98
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_correction_T_min  0.9635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.286
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         4657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.286
_refine_ls_R_factor_all          0.1768
_refine_ls_R_factor_gt           0.0996
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2355
_refine_ls_wR_factor_ref         0.2647
_reflns_number_gt                2306
_reflns_number_total             4657
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4nj01324g2.cif
_cod_data_source_block           A3:Pim
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7054656
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N11 N -0.1291(5) 0.0765(3) 0.41660(12) 0.0351(6) Uani 1 1 d .
C12 C -0.1165(6) 0.0616(4) 0.48255(15) 0.0360(7) Uani 1 1 d .
N13 N -0.3428(5) 0.1693(3) 0.50908(13) 0.0399(7) Uani 1 1 d .
C14 C -0.5079(7) 0.2563(4) 0.45837(17) 0.0429(8) Uani 1 1 d .
H14 H -0.6864 0.3436 0.4626 0.052 Uiso 1 1 calc R
C15 C -0.3816(7) 0.2006(4) 0.40150(17) 0.0389(8) Uani 1 1 d .
H15 H -0.4535 0.2397 0.3597 0.047 Uiso 1 1 calc R
N21 N 0.2245(5) -0.2581(3) 0.30157(12) 0.0367(6) Uani 1 1 d .
C22 C 0.0581(6) -0.1877(4) 0.35073(14) 0.0336(7) Uani 1 1 d .
C23 C -0.1201(7) -0.2696(4) 0.38341(16) 0.0382(8) Uani 1 1 d .
H23 H -0.2385 -0.2151 0.4179 0.046 Uiso 1 1 calc R
C24 C -0.1198(7) -0.4336(4) 0.36411(17) 0.0425(8) Uani 1 1 d .
H24 H -0.2384 -0.4936 0.3854 0.051 Uiso 1 1 calc R
C25 C 0.0536(7) -0.5077(4) 0.31404(16) 0.0429(8) Uani 1 1 d .
H25 H 0.0569 -0.6196 0.3001 0.051 Uiso 1 1 calc R
C26 C 0.2223(7) -0.4173(4) 0.28444(16) 0.0419(8) Uani 1 1 d .
H26 H 0.3435 -0.4699 0.2501 0.050 Uiso 1 1 calc R
C27 C 0.0786(7) -0.0104(4) 0.36791(15) 0.0369(7) Uani 1 1 d .
H27A H 0.2729 -0.0250 0.3838 0.044 Uiso 1 1 calc R
H27B H 0.0515 0.0664 0.3285 0.044 Uiso 1 1 calc R
C31 C 0.6199(6) -0.0015(4) 0.21965(15) 0.0365(7) Uani 1 1 d .
O31 O 0.5759(5) -0.1575(3) 0.21879(12) 0.0441(6) Uani 1 1 d .
H31 H 0.447(8) -0.156(5) 0.2443(18) 0.053 Uiso 1 1 d .
C32 C 0.8352(7) 0.0174(4) 0.16974(16) 0.0381(7) Uani 1 1 d .
H32A H 0.7818 -0.0184 0.1282 0.046 Uiso 1 1 calc R
H32B H 1.0230 -0.0649 0.1817 0.046 Uiso 1 1 calc R
O32 O 0.4996(5) 0.1090(3) 0.25691(11) 0.0461(6) Uani 1 1 d .
C33 C 0.8670(7) 0.2003(4) 0.16021(16) 0.0410(8) Uani 1 1 d .
H33A H 0.8923 0.2441 0.2026 0.049 Uiso 1 1 calc R
H33B H 1.0407 0.1935 0.1342 0.049 Uiso 1 1 calc R
C34 C 0.6134(7) 0.3293(4) 0.12724(15) 0.0380(7) Uani 1 1 d .
H34A H 0.4474 0.3538 0.1570 0.046 Uiso 1 1 calc R
H34B H 0.5647 0.2756 0.0890 0.046 Uiso 1 1 calc R
C35 C 0.6689(7) 0.5014(4) 0.10642(17) 0.0416(8) Uani 1 1 d .
H35A H 0.7339 0.5502 0.1439 0.050 Uiso 1 1 calc R
H35B H 0.8235 0.4785 0.0737 0.050 Uiso 1 1 calc R
C36 C 0.4063(7) 0.6346(4) 0.07884(17) 0.0434(8) Uani 1 1 d .
H36A H 0.3204 0.5767 0.0474 0.052 Uiso 1 1 calc R
H36B H 0.2658 0.6729 0.1140 0.052 Uiso 1 1 calc R
C37 C 0.4577(7) 0.7946(4) 0.04612(16) 0.0396(8) Uani 1 1 d .
O37 O 0.2414(6) 0.9316(4) 0.04382(14) 0.0606(8) Uani 1 1 d .
H37 H 0.242(9) 1.019(7) 0.021(2) 0.073 Uiso 1 1 d .
O38 O 0.6939(5) 0.7890(3) 0.02233(12) 0.0505(7) Uani 1 1 d .
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_3
C15 N11 C12 106.6(3) .
C15 N11 C27 123.0(3) .
C12 N11 C27 130.3(3) .
N13 C12 N11 111.5(3) .
N13 C12 C12 125.2(4) 2_556
N11 C12 C12 123.3(3) 2_556
C12 N13 C14 105.1(3) .
C15 C14 N13 110.9(3) .
C15 C14 H14 124.6 .
N13 C14 H14 124.6 .
C14 C15 N11 106.0(3) .
C14 C15 H15 127.0 .
N11 C15 H15 127.0 .
C22 N21 C26 117.7(2) .
N21 C22 C23 123.0(3) .
N21 C22 C27 114.3(2) .
C23 C22 C27 122.7(3) .
C22 C23 C24 118.0(3) .
C22 C23 H23 121.0 .
C24 C23 H23 121.0 .
C25 C24 C23 119.3(3) .
C25 C24 H24 120.3 .
C23 C24 H24 120.3 .
C24 C25 C26 118.7(3) .
C24 C25 H25 120.6 .
C26 C25 H25 120.6 .
N21 C26 C25 123.3(3) .
N21 C26 H26 118.4 .
C25 C26 H26 118.4 .
N11 C27 C22 114.2(2) .
N11 C27 H27A 108.7 .
C22 C27 H27A 108.7 .
N11 C27 H27B 108.7 .
C22 C27 H27B 108.7 .
H27A C27 H27B 107.6 .
O32 C31 O31 123.0(3) .
O32 C31 C32 125.3(3) .
O31 C31 C32 111.7(3) .
C31 O31 H31 107(3) .
C31 C32 C33 115.4(3) .
C31 C32 H32A 108.4 .
C33 C32 H32A 108.4 .
C31 C32 H32B 108.4 .
C33 C32 H32B 108.4 .
H32A C32 H32B 107.5 .
C34 C33 C32 113.1(3) .
C34 C33 H33A 109.0 .
C32 C33 H33A 109.0 .
C34 C33 H33B 109.0 .
C32 C33 H33B 109.0 .
H33A C33 H33B 107.8 .
C33 C34 C35 112.8(2) .
C33 C34 H34A 109.0 .
C35 C34 H34A 109.0 .
C33 C34 H34B 109.0 .
C35 C34 H34B 109.0 .
H34A C34 H34B 107.8 .
C36 C35 C34 112.2(2) .
C36 C35 H35A 109.2 .
C34 C35 H35A 109.2 .
C36 C35 H35B 109.2 .
C34 C35 H35B 109.2 .
H35A C35 H35B 107.9 .
C37 C36 C35 115.1(3) .
C37 C36 H36A 108.5 .
C35 C36 H36A 108.5 .
C37 C36 H36B 108.5 .
C35 C36 H36B 108.5 .
H36A C36 H36B 107.5 .
O38 C37 O37 123.7(3) .
O38 C37 C36 121.0(3) .
O37 C37 C36 115.3(3) .
C37 O37 H37 121(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C15 1.371(4) .
N11 C12 1.374(4) .
N11 C27 1.466(4) .
C12 N13 1.315(4) .
C12 C12 1.452(7) 2_556
N13 C14 1.375(4) .
C14 C15 1.355(4) .
C14 H14 0.9500 .
C15 H15 0.9500 .
N21 C22 1.333(4) .
N21 C26 1.343(4) .
C22 C23 1.391(4) .
C22 C27 1.513(4) .
C23 C24 1.391(4) .
C23 H23 0.9500 .
C24 C25 1.372(5) .
C24 H24 0.9500 .
C25 C26 1.373(4) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C31 O32 1.211(4) .
C31 O31 1.331(3) .
C31 C32 1.501(4) .
O31 H31 0.82(4) .
C32 C33 1.522(4) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C34 1.515(5) .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C34 C35 1.524(4) .
C34 H34A 0.9900 .
C34 H34B 0.9900 .
C35 C36 1.512(5) .
C35 H35A 0.9900 .
C35 H35B 0.9900 .
C36 C37 1.507(4) .
C36 H36A 0.9900 .
C36 H36B 0.9900 .
C37 O38 1.241(4) .
C37 O37 1.279(4) .
O37 H37 0.83(5) .
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
O31 H31 N21 0.82(4) 1.92(4) 2.677(3) 155(4) .
O37 H37 O38 0.83(5) 1.85(5) 2.668(3) 169(4) 2_675
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_4
C15 N11 C12 N13 -0.6(3) . .
C27 N11 C12 N13 176.9(2) . .
C15 N11 C12 C12 178.0(3) . 2_556
C27 N11 C12 C12 -4.6(5) . 2_556
N11 C12 N13 C14 0.3(3) . .
C12 C12 N13 C14 -178.3(3) 2_556 .
C12 N13 C14 C15 0.2(3) . .
N13 C14 C15 N11 -0.6(3) . .
C12 N11 C15 C14 0.7(3) . .
C27 N11 C15 C14 -177.0(2) . .
C26 N21 C22 C23 -1.6(5) . .
C26 N21 C22 C27 178.6(3) . .
N21 C22 C23 C24 1.0(5) . .
C27 C22 C23 C24 -179.2(3) . .
C22 C23 C24 C25 -0.2(5) . .
C23 C24 C25 C26 0.0(5) . .
C22 N21 C26 C25 1.5(5) . .
C24 C25 C26 N21 -0.7(5) . .
C15 N11 C27 C22 -97.1(3) . .
C12 N11 C27 C22 85.8(3) . .
N21 C22 C27 N11 172.9(3) . .
C23 C22 C27 N11 -6.9(4) . .
O32 C31 C32 C33 -9.3(5) . .
O31 C31 C32 C33 171.2(3) . .
C31 C32 C33 C34 -71.4(4) . .
C32 C33 C34 C35 -169.1(3) . .
C33 C34 C35 C36 -175.0(3) . .
C34 C35 C36 C37 -169.1(3) . .
C35 C36 C37 O38 26.0(5) . .
C35 C36 C37 O37 -155.4(3) . .
