#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:52:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180100 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/46/7054653.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_7054653
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-3 1,1'-di[(2-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                99.940(9)
_cell_angle_beta                 93.967(10)
_cell_angle_gamma                108.231(8)
_cell_formula_units_Z            1
_cell_length_a                   5.1024(10)
_cell_length_b                   8.0128(15)
_cell_length_c                   16.497(3)
_cell_measurement_reflns_used    5256
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      65.62
_cell_measurement_theta_min      2.74
_cell_volume                     625.5(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 0.952
_diffrn_measured_fraction_theta_max 0.952
_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  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9109
_diffrn_reflns_theta_full        66.73
_diffrn_reflns_theta_max         66.73
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  0.8666
_exptl_absorpt_correction_T_min  0.7983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.176
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0496
_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          0.1457
_refine_ls_wR_factor_ref         0.1580
_reflns_number_gt                1891
_reflns_number_total             2111
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4nj01324g2.cif
_cod_data_source_block           A3: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_sg_symbol_H-M      P-1
_cod_database_code               7054653
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 -0.0249(3) 0.6107(2) 0.10887(10) 0.0268(4) Uani 1 1 d .
C12 C -0.0493(4) 0.5685(3) 0.02317(12) 0.0265(5) Uani 1 1 d .
N13 N -0.1766(4) 0.6669(2) -0.01143(11) 0.0319(4) Uani 1 1 d .
C14 C -0.2387(4) 0.7742(3) 0.05461(14) 0.0332(5) Uani 1 1 d .
H14 H -0.3310 0.8588 0.0493 0.040 Uiso 1 1 calc R
C15 C -0.1486(5) 0.7414(3) 0.12876(14) 0.0318(5) Uani 1 1 d .
H15 H -0.1672 0.7970 0.1828 0.038 Uiso 1 1 calc R
N21 N 0.0271(4) 0.3166(2) 0.25643(11) 0.0295(4) Uani 1 1 d .
C22 C -0.0832(4) 0.3720(3) 0.19294(12) 0.0254(5) Uani 1 1 d .
C23 C -0.3509(4) 0.2794(3) 0.15120(13) 0.0299(5) Uani 1 1 d .
H23 H -0.4239 0.3214 0.1072 0.036 Uiso 1 1 calc R
C24 C -0.5097(5) 0.1234(3) 0.17544(14) 0.0355(5) Uani 1 1 d .
H24 H -0.6928 0.0584 0.1482 0.043 Uiso 1 1 calc R
C25 C -0.3972(5) 0.0646(3) 0.23970(14) 0.0360(5) Uani 1 1 d .
H25 H -0.5009 -0.0413 0.2568 0.043 Uiso 1 1 calc R
C26 C -0.1298(5) 0.1643(3) 0.27821(14) 0.0344(5) Uani 1 1 d .
H26 H -0.0529 0.1239 0.3220 0.041 Uiso 1 1 calc R
C27 C 0.1080(4) 0.5416(3) 0.17169(12) 0.0281(5) Uani 1 1 d .
H27A H 0.1747 0.6357 0.2230 0.034 Uiso 1 1 calc R
H27B H 0.2724 0.5168 0.1510 0.034 Uiso 1 1 calc R
C31 C 0.6869(4) 0.6100(3) 0.36510(13) 0.0304(5) Uani 1 1 d .
O31 O 0.4996(3) 0.4519(2) 0.36745(10) 0.0382(4) Uani 1 1 d .
H31 H 0.348(6) 0.416(4) 0.3236(17) 0.046 Uiso 1 1 d .
C32 C 0.9354(5) 0.6655(3) 0.43187(13) 0.0324(5) Uani 1 1 d .
H32A H 1.0250 0.5717 0.4253 0.039 Uiso 1 1 calc R
H32B H 0.8690 0.6729 0.4869 0.039 Uiso 1 1 calc R
O32 O 0.6591(3) 0.7012(2) 0.31461(10) 0.0396(4) Uani 1 1 d .
C33 C 1.1522(5) 0.8455(3) 0.42950(13) 0.0328(5) Uani 1 1 d .
H33A H 1.0590 0.9372 0.4311 0.039 Uiso 1 1 calc R
H33B H 1.2304 0.8349 0.3763 0.039 Uiso 1 1 calc R
C34 C 1.3920(5) 0.9099(3) 0.50141(13) 0.0331(5) Uani 1 1 d .
H34A H 1.3140 0.9207 0.5546 0.040 Uiso 1 1 calc R
H34B H 1.4854 0.8184 0.4998 0.040 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 106.64(17) . .
C12 N11 C27 130.00(17) . .
C15 N11 C27 123.35(17) . .
N13 C12 N11 111.33(18) . .
N13 C12 C12 124.8(2) . 2_565
N11 C12 C12 123.8(2) . 2_565
C12 N13 C14 105.21(17) . .
C15 C14 N13 110.67(18) . .
C15 C14 H14 124.7 . .
N13 C14 H14 124.7 . .
C14 C15 N11 106.14(19) . .
C14 C15 H15 126.9 . .
N11 C15 H15 126.9 . .
C26 N21 C22 117.92(18) . .
N21 C22 C23 122.27(18) . .
N21 C22 C27 114.46(17) . .
C23 C22 C27 123.26(18) . .
C22 C23 C24 118.7(2) . .
C22 C23 H23 120.7 . .
C24 C23 H23 120.7 . .
C25 C24 C23 119.4(2) . .
C25 C24 H24 120.3 . .
C23 C24 H24 120.3 . .
C26 C25 C24 118.4(2) . .
C26 C25 H25 120.8 . .
C24 C25 H25 120.8 . .
N21 C26 C25 123.3(2) . .
N21 C26 H26 118.4 . .
C25 C26 H26 118.4 . .
N11 C27 C22 113.80(16) . .
N11 C27 H27A 108.8 . .
C22 C27 H27A 108.8 . .
N11 C27 H27B 108.8 . .
C22 C27 H27B 108.8 . .
H27A C27 H27B 107.7 . .
O32 C31 O31 123.4(2) . .
O32 C31 C32 123.7(2) . .
O31 C31 C32 112.94(18) . .
C31 O31 H31 112.0(16) . .
C31 C32 C33 113.48(18) . .
C31 C32 H32A 108.9 . .
C33 C32 H32A 108.9 . .
C31 C32 H32B 108.9 . .
C33 C32 H32B 108.9 . .
H32A C32 H32B 107.7 . .
C32 C33 C34 113.63(18) . .
C32 C33 H33A 108.8 . .
C34 C33 H33A 108.8 . .
C32 C33 H33B 108.8 . .
C34 C33 H33B 108.8 . .
H33A C33 H33B 107.7 . .
C34 C34 C33 113.3(2) 2_876 .
C34 C34 H34A 108.9 2_876 .
C33 C34 H34A 108.9 . .
C34 C34 H34B 108.9 2_876 .
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 1.383(3) .
N11 C15 1.388(3) .
N11 C27 1.475(2) .
C12 N13 1.340(3) .
C12 C12 1.467(4) 2_565
N13 C14 1.386(3) .
C14 C15 1.373(3) .
C14 H14 0.9500 .
C15 H15 0.9500 .
N21 C26 1.356(3) .
N21 C22 1.359(3) .
C22 C23 1.396(3) .
C22 C27 1.518(3) .
C23 C24 1.401(3) .
C23 H23 0.9500 .
C24 C25 1.390(3) .
C24 H24 0.9500 .
C25 C26 1.388(3) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C31 O32 1.227(3) .
C31 O31 1.335(3) .
C31 C32 1.518(3) .
O31 H31 0.96(3) .
C32 C33 1.527(3) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C34 1.537(3) .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C34 C34 1.529(4) 2_876
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 0.96(3) 1.78(3) 2.722(2) 167(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 1.0(2) . .
C27 N11 C12 N13 -177.60(17) . .
C15 N11 C12 C12 -178.2(2) . 2_565
C27 N11 C12 C12 3.2(4) . 2_565
N11 C12 N13 C14 -0.7(2) . .
C12 C12 N13 C14 178.5(2) 2_565 .
C12 N13 C14 C15 0.2(2) . .
N13 C14 C15 N11 0.4(2) . .
C12 N11 C15 C14 -0.8(2) . .
C27 N11 C15 C14 177.91(17) . .
C26 N21 C22 C23 1.0(3) . .
C26 N21 C22 C27 -179.00(17) . .
N21 C22 C23 C24 -0.5(3) . .
C27 C22 C23 C24 179.59(18) . .
C22 C23 C24 C25 -0.3(3) . .
C23 C24 C25 C26 0.4(3) . .
C22 N21 C26 C25 -0.9(3) . .
C24 C25 C26 N21 0.2(3) . .
C12 N11 C27 C22 -87.3(2) . .
C15 N11 C27 C22 94.4(2) . .
N21 C22 C27 N11 -173.83(16) . .
C23 C22 C27 N11 6.1(3) . .
O32 C31 C32 C33 -1.0(3) . .
O31 C31 C32 C33 179.61(17) . .
C31 C32 C33 C34 175.12(18) . .
C32 C33 C34 C34 180.0(2) . 2_876
