#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:52:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180100 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/46/7054645.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_7054645
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) (C4 H6 O4)
;
_chemical_formula_sum            'C22 H22 N6 O4'
_chemical_formula_weight         434.46
_chemical_name_systematic
;
TW-2B-19 1,1'-di[(4-pyridyl)methyl]-2,2'-biimidazole, HOOC-(CH2)2-COOH
;
_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                69.536(7)
_cell_angle_beta                 89.567(7)
_cell_angle_gamma                85.993(7)
_cell_formula_units_Z            1
_cell_length_a                   4.8468(8)
_cell_length_b                   9.2594(16)
_cell_length_c                   12.245(2)
_cell_measurement_reflns_used    4840
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      67.98
_cell_measurement_theta_min      3.85
_cell_volume                     513.51(15)
_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 0.969
_diffrn_measured_fraction_theta_max 0.962
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6345
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         67.98
_diffrn_reflns_theta_min         3.85
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.543
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.236
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0507
_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)+(0.0800P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1400
_reflns_number_gt                1660
_reflns_number_total             1799
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4nj01324g2.cif
_cod_data_source_block           A1:Suc
_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_cell_volume        513.50(15)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7054645
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 0.7789(3) 0.49089(16) 0.89292(12) 0.0167(4) Uani 1 1 d .
C12 C 0.5905(3) 0.54818(19) 0.95572(14) 0.0159(4) Uani 1 1 d .
N13 N 0.5947(3) 0.70183(17) 0.92504(13) 0.0194(4) Uani 1 1 d .
C14 C 0.7917(4) 0.7437(2) 0.83850(15) 0.0203(4) Uani 1 1 d .
H14 H 0.8405 0.8464 0.7992 0.024 Uiso 1 1 calc R
C15 C 0.9051(4) 0.6168(2) 0.81777(15) 0.0206(4) Uani 1 1 d .
H15 H 1.0433 0.6152 0.7627 0.025 Uiso 1 1 calc R
N21 N 0.2531(3) 0.19077(17) 0.69176(13) 0.0202(4) Uani 1 1 d .
C22 C 0.3802(4) 0.0881(2) 0.78888(16) 0.0212(4) Uani 1 1 d .
H22 H 0.3378 -0.0170 0.8128 0.025 Uiso 1 1 calc R
C23 C 0.5700(4) 0.1302(2) 0.85496(15) 0.0208(4) Uani 1 1 d .
H23 H 0.6572 0.0545 0.9218 0.025 Uiso 1 1 calc R
C24 C 0.6318(3) 0.2852(2) 0.82208(15) 0.0180(4) Uani 1 1 d .
C25 C 0.5044(4) 0.3912(2) 0.72075(16) 0.0208(4) Uani 1 1 d .
H25 H 0.5440 0.4968 0.6948 0.025 Uiso 1 1 calc R
C26 C 0.3179(4) 0.3394(2) 0.65820(15) 0.0208(4) Uani 1 1 d .
H26 H 0.2334 0.4119 0.5892 0.025 Uiso 1 1 calc R
C27 C 0.8363(4) 0.3308(2) 0.89647(15) 0.0196(4) Uani 1 1 d .
H27 H 0.8285 0.2595 0.9782 0.024 Uiso 1 1 calc R
H27B H 1.0259 0.3193 0.8685 0.024 Uiso 1 1 calc R
C31 C -0.2497(3) 0.15781(19) 0.50365(15) 0.0172(4) Uani 1 1 d .
O31 O -0.1272(3) 0.06880(14) 0.60353(10) 0.0211(3) Uani 1 1 d .
H31 H 0.000(5) 0.123(3) 0.625(2) 0.025 Uiso 1 1 d .
O32 O -0.1865(3) 0.28969(14) 0.44893(11) 0.0257(4) Uani 1 1 d .
C32 C -0.4762(4) 0.08359(19) 0.46131(15) 0.0180(4) Uani 1 1 d .
H32A H -0.4301 0.0849 0.3821 0.022 Uiso 1 1 calc R
H32B H -0.6516 0.1477 0.4550 0.022 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C12 N11 C15 106.56(14) . .
C12 N11 C27 129.28(15) . .
C15 N11 C27 124.12(15) . .
N13 C12 N11 111.28(15) . .
N13 C12 C12 124.79(19) . 2_667
N11 C12 C12 123.93(19) . 2_667
C12 N13 C14 105.04(14) . .
C15 C14 N13 110.66(16) . .
C15 C14 H14 124.7 . .
N13 C14 H14 124.7 . .
C14 C15 N11 106.45(16) . .
C14 C15 H15 126.8 . .
N11 C15 H15 126.8 . .
C26 N21 C22 117.87(15) . .
N21 C22 C23 122.74(17) . .
N21 C22 H22 118.6 . .
C23 C22 H22 118.6 . .
C22 C23 C24 119.47(16) . .
C22 C23 H23 120.3 . .
C24 C23 H23 120.3 . .
C25 C24 C23 117.96(16) . .
C25 C24 C27 122.93(16) . .
C23 C24 C27 119.10(15) . .
C24 C25 C26 119.12(16) . .
C24 C25 H25 120.4 . .
C26 C25 H25 120.4 . .
N21 C26 C25 122.81(16) . .
N21 C26 H26 118.6 . .
C25 C26 H26 118.6 . .
N11 C27 C24 112.70(14) . .
N11 C27 H27 109.1 . .
C24 C27 H27 109.1 . .
N11 C27 H27B 109.1 . .
C24 C27 H27B 109.1 . .
H27 C27 H27B 107.8 . .
O32 C31 O31 123.27(15) . .
O32 C31 C32 122.10(15) . .
O31 C31 C32 114.63(14) . .
C31 O31 H31 109.2(14) . .
C31 C32 C32 115.37(17) . 2_456
C31 C32 H32A 108.4 . .
C32 C32 H32A 108.4 2_456 .
C31 C32 H32B 108.4 . .
C32 C32 H32B 108.4 2_456 .
H32A C32 H32B 107.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C12 1.383(2) .
N11 C15 1.386(2) .
N11 C27 1.474(2) .
C12 N13 1.340(2) .
C12 C12 1.470(3) 2_667
N13 C14 1.390(2) .
C14 C15 1.365(3) .
C14 H14 0.9500 .
C15 H15 0.9500 .
N21 C26 1.351(2) .
N21 C22 1.355(2) .
C22 C23 1.391(3) .
C22 H22 0.9500 .
C23 C24 1.402(3) .
C23 H23 0.9500 .
C24 C25 1.400(2) .
C24 C27 1.527(2) .
C25 C26 1.400(2) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C27 H27 0.9900 .
C27 H27B 0.9900 .
C31 O32 1.229(2) .
C31 O31 1.329(2) .
C31 C32 1.520(2) .
O31 H31 0.92(3) .
C32 C32 1.539(3) 2_456
C32 H32A 0.9900 .
C32 H32B 0.9900 .
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
O31 H31 N21 0.92(3) 1.74(3) 2.6484(19) 168(2)
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 -0.76(18) . .
C27 N11 C12 N13 -178.14(14) . .
C15 N11 C12 C12 179.08(19) . 2_667
C27 N11 C12 C12 1.7(3) . 2_667
N11 C12 N13 C14 0.61(18) . .
C12 C12 N13 C14 -179.2(2) 2_667 .
C12 N13 C14 C15 -0.24(19) . .
N13 C14 C15 N11 -0.21(19) . .
C12 N11 C15 C14 0.57(18) . .
C27 N11 C15 C14 178.12(14) . .
C26 N21 C22 C23 0.7(3) . .
N21 C22 C23 C24 1.0(3) . .
C22 C23 C24 C25 -2.0(3) . .
C22 C23 C24 C27 178.83(15) . .
C23 C24 C25 C26 1.3(3) . .
C27 C24 C25 C26 -179.57(16) . .
C22 N21 C26 C25 -1.5(3) . .
C24 C25 C26 N21 0.4(3) . .
C12 N11 C27 C24 82.2(2) . .
C15 N11 C27 C24 -94.76(19) . .
C25 C24 C27 N11 30.6(2) . .
C23 C24 C27 N11 -150.28(15) . .
O32 C31 C32 C32 178.50(18) . 2_456
O31 C31 C32 C32 -1.4(3) . 2_456
