#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:52:43 +0100 (vie 25 de mar de 2016) $
#$Revision: 180100 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/46/7054648.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_7054648
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) (C10 H18 O4)
;
_chemical_formula_sum            'C28 H34 N6 O4'
_chemical_formula_weight         518.61
_chemical_name_systematic
;
TW-2B-22 1,1'-di[(3-pyridyl)methyl]-2,2'-biimidazole, HOOCH-(CH2)8-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                93.630(7)
_cell_angle_beta                 98.988(7)
_cell_angle_gamma                104.670(7)
_cell_formula_units_Z            1
_cell_length_a                   5.6320(7)
_cell_length_b                   6.8450(8)
_cell_length_c                   17.748(2)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      67.58
_cell_measurement_theta_min      2.54
_cell_volume                     649.97(14)
_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 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4606
_diffrn_reflns_theta_full        68.93
_diffrn_reflns_theta_max         68.93
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  0.9299
_exptl_absorpt_correction_T_min  0.7876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.544
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         4606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.544
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0550
_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          0.1820
_refine_ls_wR_factor_ref         0.1976
_reflns_number_gt                3942
_reflns_number_total             4606
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4nj01324g2.cif
_cod_data_source_block           A1:Seb
_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        649.97(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7054648
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 -0.2750(2) 0.02352(18) 0.42867(7) 0.0224(3) Uani 1 1 d .
C12 C -0.1230(3) -0.0577(2) 0.47955(8) 0.0207(4) Uani 1 1 d .
N13 N -0.2305(3) -0.25257(18) 0.48529(7) 0.0237(3) Uani 1 1 d .
C14 C -0.4573(3) -0.2987(2) 0.43616(8) 0.0243(4) Uani 1 1 d .
H14 H -0.5757 -0.4280 0.4278 0.029 Uiso 1 1 calc R
C15 C -0.4877(3) -0.1322(2) 0.40115(9) 0.0261(4) Uani 1 1 d .
H15 H -0.6277 -0.1248 0.3650 0.031 Uiso 1 1 calc R
N21 N 0.2035(3) 0.43819(19) 0.23989(7) 0.0254(3) Uani 1 1 d .
C22 C 0.1930(3) 0.2550(2) 0.26512(9) 0.0257(4) Uani 1 1 d .
H22 H 0.2900 0.1748 0.2460 0.031 Uiso 1 1 calc R
C23 C 0.0446(3) 0.1787(2) 0.31843(9) 0.0250(4) Uani 1 1 d .
H23 H 0.0409 0.0485 0.3346 0.030 Uiso 1 1 calc R
C24 C -0.0980(3) 0.2945(2) 0.34775(8) 0.0231(4) Uani 1 1 d .
C25 C -0.0946(3) 0.4806(2) 0.31817(9) 0.0249(4) Uani 1 1 d .
H25 H -0.1954 0.5614 0.3345 0.030 Uiso 1 1 calc R
C26 C 0.0556(3) 0.5457(2) 0.26523(9) 0.0259(4) Uani 1 1 d .
H26 H 0.0549 0.6717 0.2458 0.031 Uiso 1 1 calc R
C27 C -0.2468(3) 0.2340(2) 0.41057(9) 0.0233(4) Uani 1 1 d .
H27A H -0.1650 0.3266 0.4578 0.028 Uiso 1 1 calc R
H27B H -0.4150 0.2540 0.3952 0.028 Uiso 1 1 calc R
C31 C 0.5411(3) 0.8241(2) 0.15581(9) 0.0248(4) Uani 1 1 d .
O31 O 0.5395(2) 0.62961(16) 0.15865(7) 0.0332(3) Uani 1 1 d .
H31 H 0.405(4) 0.555(3) 0.1898(12) 0.040 Uiso 1 1 d .
O32 O 0.4045(3) 0.90181(17) 0.18739(8) 0.0425(4) Uani 1 1 d .
C32 C 0.7245(3) 0.9313(2) 0.10851(9) 0.0234(4) Uani 1 1 d .
H32A H 0.6952 0.8485 0.0585 0.028 Uiso 1 1 calc R
H32B H 0.8950 0.9373 0.1349 0.028 Uiso 1 1 calc R
C33 C 0.7141(3) 1.1478(2) 0.09339(9) 0.0229(4) Uani 1 1 d .
H33A H 0.5441 1.1448 0.0674 0.028 Uiso 1 1 calc R
H33B H 0.7505 1.2344 0.1429 0.028 Uiso 1 1 calc R
C34 C 0.9034(3) 1.2391(2) 0.04314(9) 0.0240(4) Uani 1 1 d .
H34A H 0.8640 1.1522 -0.0063 0.029 Uiso 1 1 calc R
H34B H 1.0718 1.2368 0.0688 0.029 Uiso 1 1 calc R
C35 C 0.9091(3) 1.4589(2) 0.02672(9) 0.0243(4) Uani 1 1 d .
H35A H 0.7394 1.4632 0.0032 0.029 Uiso 1 1 calc R
H35B H 0.9577 1.5479 0.0758 0.029 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
C15 N11 C12 106.17(12) . .
C15 N11 C27 123.17(13) . .
C12 N11 C27 130.31(12) . .
N13 C12 N11 111.26(13) . .
N13 C12 C12 125.29(16) . 2_556
N11 C12 C12 123.44(16) . 2_556
C12 N13 C14 105.49(12) . .
C15 C14 N13 110.41(14) . .
C15 C14 H14 124.8 . .
N13 C14 H14 124.8 . .
C14 C15 N11 106.67(14) . .
C14 C15 H15 126.7 . .
N11 C15 H15 126.7 . .
C22 N21 C26 117.76(13) . .
N21 C22 C23 122.47(14) . .
N21 C22 H22 118.8 . .
C23 C22 H22 118.8 . .
C24 C23 C22 119.74(13) . .
C24 C23 H23 120.1 . .
C22 C23 H23 120.1 . .
C23 C24 C25 117.14(14) . .
C23 C24 C27 123.79(13) . .
C25 C24 C27 119.03(13) . .
C26 C25 C24 119.80(14) . .
C26 C25 H25 120.1 . .
C24 C25 H25 120.1 . .
N21 C26 C25 122.93(13) . .
N21 C26 H26 118.5 . .
C25 C26 H26 118.5 . .
N11 C27 C24 115.12(12) . .
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 122.64(15) . .
O32 C31 C32 125.12(14) . .
O31 C31 C32 112.22(13) . .
C31 O31 H31 111.2(10) . .
C31 C32 C33 115.61(13) . .
C31 C32 H32A 108.4 . .
C33 C32 H32A 108.4 . .
C31 C32 H32B 108.4 . .
C33 C32 H32B 108.4 . .
H32A C32 H32B 107.4 . .
C34 C33 C32 110.94(12) . .
C34 C33 H33A 109.5 . .
C32 C33 H33A 109.5 . .
C34 C33 H33B 109.5 . .
C32 C33 H33B 109.5 . .
H33A C33 H33B 108.0 . .
C33 C34 C35 114.23(13) . .
C33 C34 H34A 108.7 . .
C35 C34 H34A 108.7 . .
C33 C34 H34B 108.7 . .
C35 C34 H34B 108.7 . .
H34A C34 H34B 107.6 . .
C35 C35 C34 112.73(16) 2_785 .
C35 C35 H35A 109.0 2_785 .
C34 C35 H35A 109.0 . .
C35 C35 H35B 109.0 2_785 .
C34 C35 H35B 109.0 . .
H35A C35 H35B 107.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C15 1.384(2) .
N11 C12 1.3854(19) .
N11 C27 1.4709(17) .
C12 N13 1.3356(19) .
C12 C12 1.459(3) 2_556
N13 C14 1.380(2) .
C14 C15 1.368(2) .
C14 H14 0.9500 .
C15 H15 0.9500 .
N21 C22 1.3484(19) .
N21 C26 1.350(2) .
C22 C23 1.398(2) .
C22 H22 0.9500 .
C23 C24 1.395(2) .
C23 H23 0.9500 .
C24 C25 1.405(2) .
C24 C27 1.514(2) .
C25 C26 1.381(2) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C31 O32 1.222(2) .
C31 O31 1.3332(18) .
C31 C32 1.508(2) .
O31 H31 1.05(2) .
C32 C33 1.5370(19) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C34 1.534(2) .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C34 C35 1.544(2) .
C34 H34A 0.9900 .
C34 H34B 0.9900 .
C35 C35 1.531(3) 2_785
C35 H35A 0.9900 .
C35 H35B 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 1.05(2) 1.63(2) 2.6857(18) 178.1(17)
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 -0.51(16) . .
C27 N11 C12 N13 172.77(14) . .
C15 N11 C12 C12 179.02(17) . 2_556
C27 N11 C12 C12 -7.7(3) . 2_556
N11 C12 N13 C14 0.52(16) . .
C12 C12 N13 C14 -179.00(18) 2_556 .
C12 N13 C14 C15 -0.34(17) . .
N13 C14 C15 N11 0.03(18) . .
C12 N11 C15 C14 0.28(17) . .
C27 N11 C15 C14 -173.60(13) . .
C26 N21 C22 C23 -2.9(2) . .
N21 C22 C23 C24 -0.5(2) . .
C22 C23 C24 C25 3.5(2) . .
C22 C23 C24 C27 -174.48(14) . .
C23 C24 C25 C26 -3.2(2) . .
C27 C24 C25 C26 174.90(14) . .
C22 N21 C26 C25 3.3(2) . .
C24 C25 C26 N21 -0.2(2) . .
C15 N11 C27 C24 -99.78(17) . .
C12 N11 C27 C24 87.93(18) . .
C23 C24 C27 N11 -12.1(2) . .
C25 C24 C27 N11 169.98(13) . .
O32 C31 C32 C33 -6.5(2) . .
O31 C31 C32 C33 172.29(12) . .
C31 C32 C33 C34 -178.49(13) . .
C32 C33 C34 C35 -178.68(12) . .
C33 C34 C35 C35 -177.20(16) . 2_785
