#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:52:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180100 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/46/7054647.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_7054647
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) (C8 H14 O4)
;
_chemical_formula_sum            'C26 H30 N6 O4'
_chemical_formula_weight         490.56
_chemical_name_systematic
;
TW-2B-21 1,1'-di[(4-pyridyl)methyl]-2,2'-biimidazole, HOOC-(CH2)6-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                87.236(4)
_cell_angle_beta                 82.669(4)
_cell_angle_gamma                75.451(4)
_cell_formula_units_Z            1
_cell_length_a                   5.6196(11)
_cell_length_b                   6.7825(13)
_cell_length_c                   16.078(3)
_cell_measurement_reflns_used    4190
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.37
_cell_measurement_theta_min      5.69
_cell_volume                     588.2(2)
_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 0.971
_diffrn_measured_fraction_theta_max 0.904
_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  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10698
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         32.75
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.9662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0458
_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)+(0.0750P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                3433
_reflns_number_total             3929
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4nj01324g2.cif
_cod_data_source_block           A1:Sub
_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        588.22(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7054647
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 -0.25886(14) 0.95226(11) 0.07691(5) 0.02114(16) Uani 1 1 d .
C12 C -0.11832(16) 1.05018(13) 0.02219(5) 0.01965(17) Uani 1 1 d .
N13 N -0.22540(15) 1.24667(12) 0.01589(5) 0.02295(17) Uani 1 1 d .
C14 C -0.44238(18) 1.27623(14) 0.06874(6) 0.02460(19) Uani 1 1 d .
H14 H -0.5602 1.4034 0.0775 0.030 Uiso 1 1 calc R
C15 C -0.46479(18) 1.09730(15) 0.10693(6) 0.02503(19) Uani 1 1 d .
H15 H -0.5973 1.0771 0.1466 0.030 Uiso 1 1 calc R
N21 N 0.25682(16) 0.47548(13) 0.28008(5) 0.02466(17) Uani 1 1 d .
C22 C 0.24074(19) 0.66692(15) 0.25334(6) 0.02549(19) Uani 1 1 d .
H22 H 0.3423 0.7413 0.2742 0.031 Uiso 1 1 calc R
C23 C 0.08123(19) 0.76194(14) 0.19609(6) 0.02427(19) Uani 1 1 d .
H23 H 0.0727 0.8993 0.1790 0.029 Uiso 1 1 calc R
C24 C -0.06478(16) 0.65488(13) 0.16428(6) 0.02019(17) Uani 1 1 d .
C25 C -0.05656(18) 0.45892(14) 0.19538(6) 0.02418(19) Uani 1 1 d .
H25 H -0.1611 0.3831 0.1774 0.029 Uiso 1 1 calc R
C26 C 0.10565(19) 0.37590(14) 0.25276(6) 0.02497(19) Uani 1 1 d .
H26 H 0.1099 0.2419 0.2738 0.030 Uiso 1 1 calc R
C27 C -0.22659(17) 0.73601(14) 0.09651(6) 0.02236(18) Uani 1 1 d .
H27A H -0.1548 0.6586 0.0448 0.027 Uiso 1 1 calc R
H27B H -0.3917 0.7101 0.1137 0.027 Uiso 1 1 calc R
C31 C 0.60586(18) 0.06174(14) 0.37185(6) 0.02433(19) Uani 1 1 d .
O31 O 0.61267(16) 0.25458(12) 0.36452(6) 0.0355(2) Uani 1 1 d .
H31 H 0.482(3) 0.331(3) 0.3341(11) 0.043 Uiso 1 1 d .
O32 O 0.45836(19) -0.00493(13) 0.34100(7) 0.0472(3) Uani 1 1 d .
C32 C 0.79651(18) -0.05906(14) 0.42398(6) 0.02456(19) Uani 1 1 d .
H32A H 0.7724 0.0070 0.4791 0.029 Uiso 1 1 calc R
H32B H 0.9623 -0.0530 0.3963 0.029 Uiso 1 1 calc R
C33 C 0.79382(18) -0.28080(13) 0.43898(6) 0.02376(18) Uani 1 1 d .
H33A H 0.8183 -0.3494 0.3845 0.029 Uiso 1 1 calc R
H33B H 0.6308 -0.2896 0.4683 0.029 Uiso 1 1 calc R
C34 C 0.99667(18) -0.38855(14) 0.49139(6) 0.02534(19) Uani 1 1 d .
H34A H 1.1588 -0.3779 0.4618 0.030 Uiso 1 1 calc R
H34B H 0.9717 -0.3182 0.5455 0.030 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 0.0033 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_1
_geom_angle_site_symmetry_3
C12 N11 C15 106.49(8) . .
C12 N11 C27 130.22(8) . .
C15 N11 C27 122.98(8) . .
N13 C12 N11 111.44(8) . .
N13 C12 C12 124.83(10) . 2_575
N11 C12 C12 123.73(10) . 2_575
C12 N13 C14 105.38(8) . .
C15 C14 N13 110.22(8) . .
C15 C14 H14 124.9 . .
N13 C14 H14 124.9 . .
C14 C15 N11 106.47(9) . .
C14 C15 H15 126.8 . .
N11 C15 H15 126.8 . .
C22 N21 C26 117.98(8) . .
N21 C22 C23 122.53(9) . .
N21 C22 H22 118.7 . .
C23 C22 H22 118.7 . .
C24 C23 C22 119.37(8) . .
C24 C23 H23 120.3 . .
C22 C23 H23 120.3 . .
C23 C24 C25 117.90(8) . .
C23 C24 C27 123.80(8) . .
C25 C24 C27 118.28(8) . .
C26 C25 C24 119.07(9) . .
C26 C25 H25 120.5 . .
C24 C25 H25 120.5 . .
N21 C26 C25 122.97(9) . .
N21 C26 H26 118.5 . .
C25 C26 H26 118.5 . .
N11 C27 C24 115.18(7) . .
N11 C27 H27A 108.5 . .
C24 C27 H27A 108.5 . .
N11 C27 H27B 108.5 . .
C24 C27 H27B 108.5 . .
H27A C27 H27B 107.5 . .
O32 C31 O31 122.81(9) . .
O32 C31 C32 125.16(9) . .
O31 C31 C32 112.02(8) . .
C31 O31 H31 110.6(10) . .
C31 C32 C33 115.51(8) . .
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 . .
C32 C33 C34 110.88(8) . .
C32 C33 H33A 109.5 . .
C34 C33 H33A 109.5 . .
C32 C33 H33B 109.5 . .
C34 C33 H33B 109.5 . .
H33A C33 H33B 108.1 . .
C34 C34 C33 113.38(10) 2_746 .
C34 C34 H34A 108.9 2_746 .
C33 C34 H34A 108.9 . .
C34 C34 H34B 108.9 2_746 .
C33 C34 H34B 108.9 . .
H34A C34 H34B 107.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C12 1.3670(11) .
N11 C15 1.3679(12) .
N11 C27 1.4560(11) .
C12 N13 1.3222(11) .
C12 C12 1.4460(17) 2_575
N13 C14 1.3705(13) .
C14 C15 1.3605(13) .
C14 H14 0.9500 .
C15 H15 0.9500 .
N21 C22 1.3327(12) .
N21 C26 1.3353(13) .
C22 C23 1.3890(13) .
C22 H22 0.9500 .
C23 C24 1.3799(13) .
C23 H23 0.9500 .
C24 C25 1.3891(12) .
C24 C27 1.5035(13) .
C25 C26 1.3805(13) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C31 O32 1.2051(13) .
C31 O31 1.3173(12) .
C31 C32 1.4979(13) .
O31 H31 0.961(18) .
C32 C33 1.5152(13) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C34 1.5201(13) .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C34 C34 1.5157(18) 2_746
C34 H34A 0.9900 .
C34 H34B 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 0.961(18) 1.700(18) 2.6604(12) 177.3(15)
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 -0.53(11) . .
C27 N11 C12 N13 173.04(9) . .
C15 N11 C12 C12 178.96(11) . 2_575
C27 N11 C12 C12 -7.47(17) . 2_575
N11 C12 N13 C14 0.21(10) . .
C12 C12 N13 C14 -179.27(11) 2_575 .
C12 N13 C14 C15 0.20(11) . .
N13 C14 C15 N11 -0.52(12) . .
C12 N11 C15 C14 0.62(11) . .
C27 N11 C15 C14 -173.53(8) . .
C26 N21 C22 C23 -2.69(15) . .
N21 C22 C23 C24 -0.93(16) . .
C22 C23 C24 C25 4.00(14) . .
C22 C23 C24 C27 -174.33(9) . .
C23 C24 C25 C26 -3.53(14) . .
C27 C24 C25 C26 174.90(9) . .
C22 N21 C26 C25 3.20(15) . .
C24 C25 C26 N21 -0.08(16) . .
C12 N11 C27 C24 87.29(12) . .
C15 N11 C27 C24 -100.06(11) . .
C23 C24 C27 N11 -11.54(13) . .
C25 C24 C27 N11 170.12(8) . .
O32 C31 C32 C33 -1.27(16) . .
O31 C31 C32 C33 177.31(9) . .
C31 C32 C33 C34 179.21(9) . .
C32 C33 C34 C34 179.96(10) . 2_746
