# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_A1:Suc

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-2B-19 1,1'-di[(4-pyridyl)methyl]-2,2'-biimidazole, HOOC-(CH2)2-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H16 N6) (C4 H6 O4)
;
_chemical_formula_sum            'C22 H22 N6 O4'
_chemical_formula_weight         434.46

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8468(8)
_cell_length_b                   9.2594(16)
_cell_length_c                   12.245(2)
_cell_angle_alpha                69.536(7)
_cell_angle_beta                 89.567(7)
_cell_angle_gamma                85.993(7)
_cell_volume                     513.50(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4840
_cell_measurement_theta_min      3.85
_cell_measurement_theta_max      67.98

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.543
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             228
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6345
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.85
_diffrn_reflns_theta_max         67.98
_reflns_number_total             1799
_reflns_number_gt                1660
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1799
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1400
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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 ?

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 0.92(3) 1.74(3) 2.6484(19) 168(2) .

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.098
_database_code_depnum_ccdc_archive 'CCDC 1016833'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_A1:Adi

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-2B-20 1,1'-di[(4-pyridyl)methyl]-2,2'-biimidazole, HOOC-(CH2)4-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H16 N6) (C6 H10 O4)
;
_chemical_formula_sum            'C24 H26 N6 O4'
_chemical_formula_weight         462.51

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5146(11)
_cell_length_b                   6.8100(14)
_cell_length_c                   15.254(3)
_cell_angle_alpha                79.288(6)
_cell_angle_beta                 85.259(6)
_cell_angle_gamma                75.952(5)
_cell_volume                     545.60(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3953
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      32.16

_exptl_crystal_description       plate
_exptl_crystal_colour            bronze
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9634
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7187
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         32.02
_reflns_number_total             3167
_reflns_number_gt                2613
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3167
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1358
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.25442(18) 0.92630(14) 0.08335(6) 0.0212(2) Uani 1 1 d . . .
C12 C 0.3858(2) 1.04267(16) 0.02392(7) 0.0197(2) Uani 1 1 d . . .
N13 N 0.27774(18) 1.24141(14) 0.01650(6) 0.0225(2) Uani 1 1 d . . .
C14 C 0.0703(2) 1.25292(18) 0.07374(8) 0.0238(2) Uani 1 1 d . . .
H14A H -0.0453 1.3766 0.0828 0.029 Uiso 1 1 calc R . .
C15 C 0.0548(2) 1.06128(18) 0.11543(8) 0.0248(2) Uani 1 1 d . . .
H15A H -0.0700 1.0275 0.1584 0.030 Uiso 1 1 calc R . .
N21 N 0.81496(19) 0.37803(15) 0.30474(6) 0.0247(2) Uani 1 1 d . . .
C22 C 0.6584(2) 0.28790(18) 0.27328(8) 0.0252(2) Uani 1 1 d . . .
H22A H 0.6679 0.1463 0.2950 0.030 Uiso 1 1 calc R . .
C23 C 0.4840(2) 0.39051(18) 0.21082(8) 0.0243(2) Uani 1 1 d . . .
H23A H 0.3766 0.3202 0.1903 0.029 Uiso 1 1 calc R . .
C24 C 0.4667(2) 0.59806(17) 0.17816(7) 0.0204(2) Uani 1 1 d . . .
C25 C 0.6203(2) 0.69393(18) 0.21370(8) 0.0243(2) Uani 1 1 d . . .
H25A H 0.6085 0.8370 0.1955 0.029 Uiso 1 1 calc R . .
C26 C 0.7919(2) 0.57932(19) 0.27611(8) 0.0257(2) Uani 1 1 d . . .
H26A H 0.8975 0.6467 0.2995 0.031 Uiso 1 1 calc R . .
C27 C 0.2885(2) 0.70382(17) 0.10497(8) 0.0219(2) Uani 1 1 d . . .
H27A H 0.3499 0.6452 0.0503 0.026 Uiso 1 1 calc R . .
H27B H 0.1235 0.6724 0.1227 0.026 Uiso 1 1 calc R . .
C31 C 1.1911(2) -0.06582(17) 0.40333(8) 0.0243(2) Uani 1 1 d . . .
O31 O 1.17239(19) 0.12860(14) 0.40844(7) 0.0352(3) Uani 1 1 d . . .
H31 H 1.047(3) 0.209(3) 0.3734(12) 0.042 Uiso 1 1 d . . .
O32 O 1.0594(2) -0.11948(15) 0.35735(8) 0.0440(3) Uani 1 1 d . . .
C32 C 1.3941(2) -0.20755(17) 0.45984(8) 0.0247(2) Uani 1 1 d . . .
H32A H 1.3810 -0.1645 0.5189 0.030 Uiso 1 1 calc R . .
H32B H 1.5581 -0.1917 0.4316 0.030 Uiso 1 1 calc R . .
C33 C 1.3887(2) -0.43257(17) 0.47388(8) 0.0234(2) Uani 1 1 d . . .
H33A H 1.3912 -0.4752 0.4151 0.028 Uiso 1 1 calc R . .
H33B H 1.2315 -0.4521 0.5068 0.028 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C12 1.3702(14) . ?
N11 C15 1.3722(15) . ?
N11 C27 1.4580(14) . ?
C12 N13 1.3275(14) . ?
C12 C12 1.452(2) 2_675 ?
N13 C14 1.3763(15) . ?
C14 C15 1.3606(16) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
N21 C22 1.3368(16) . ?
N21 C26 1.3371(15) . ?
C22 C23 1.3782(16) . ?
C22 H22A 0.9500 . ?
C23 C24 1.3913(15) . ?
C23 H23A 0.9500 . ?
C24 C25 1.3835(16) . ?
C24 C27 1.5064(15) . ?
C25 C26 1.3873(17) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C31 O32 1.2088(15) . ?
C31 O31 1.3193(14) . ?
C31 C32 1.5015(16) . ?
O31 H31 0.91(2) . ?
C32 C33 1.5146(16) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C33 1.526(2) 2_846 ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

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
_geom_angle_publ_flag
C12 N11 C15 106.49(9) . . ?
C12 N11 C27 130.00(9) . . ?
C15 N11 C27 123.20(9) . . ?
N13 C12 N11 111.28(10) . . ?
N13 C12 C12 124.94(12) . 2_675 ?
N11 C12 C12 123.78(12) . 2_675 ?
C12 N13 C14 105.47(9) . . ?
C15 C14 N13 110.06(10) . . ?
C15 C14 H14A 125.0 . . ?
N13 C14 H14A 125.0 . . ?
C14 C15 N11 106.69(10) . . ?
C14 C15 H15A 126.7 . . ?
N11 C15 H15A 126.7 . . ?
C22 N21 C26 117.54(10) . . ?
N21 C22 C23 123.18(11) . . ?
N21 C22 H22A 118.4 . . ?
C23 C22 H22A 118.4 . . ?
C22 C23 C24 119.35(10) . . ?
C22 C23 H23A 120.3 . . ?
C24 C23 H23A 120.3 . . ?
C25 C24 C23 117.55(10) . . ?
C25 C24 C27 123.82(10) . . ?
C23 C24 C27 118.60(10) . . ?
C24 C25 C26 119.44(11) . . ?
C24 C25 H25A 120.3 . . ?
C26 C25 H25A 120.3 . . ?
N21 C26 C25 122.81(11) . . ?
N21 C26 H26A 118.6 . . ?
C25 C26 H26A 118.6 . . ?
N11 C27 C24 115.22(9) . . ?
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 122.83(11) . . ?
O32 C31 C32 125.10(11) . . ?
O31 C31 C32 112.06(10) . . ?
C31 O31 H31 109.2(11) . . ?
C31 C32 C33 114.81(10) . . ?
C31 C32 H32A 108.6 . . ?
C33 C32 H32A 108.6 . . ?
C31 C32 H32B 108.6 . . ?
C33 C32 H32B 108.6 . . ?
H32A C32 H32B 107.5 . . ?
C32 C33 C33 111.52(12) . 2_846 ?
C32 C33 H33A 109.3 . . ?
C33 C33 H33A 109.3 2_846 . ?
C32 C33 H33B 109.3 . . ?
C33 C33 H33B 109.3 2_846 . ?
H33A C33 H33B 108.0 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 C12 N13 -0.75(12) . . . . ?
C27 N11 C12 N13 172.80(10) . . . . ?
C15 N11 C12 C12 178.94(13) . . . 2_675 ?
C27 N11 C12 C12 -7.5(2) . . . 2_675 ?
N11 C12 N13 C14 0.38(12) . . . . ?
C12 C12 N13 C14 -179.31(13) 2_675 . . . ?
C12 N13 C14 C15 0.15(13) . . . . ?
N13 C14 C15 N11 -0.60(13) . . . . ?
C12 N11 C15 C14 0.80(12) . . . . ?
C27 N11 C15 C14 -173.29(10) . . . . ?
C26 N21 C22 C23 2.69(18) . . . . ?
N21 C22 C23 C24 -0.08(19) . . . . ?
C22 C23 C24 C25 -2.90(17) . . . . ?
C22 C23 C24 C27 175.48(10) . . . . ?
C23 C24 C25 C26 3.25(17) . . . . ?
C27 C24 C25 C26 -175.04(11) . . . . ?
C22 N21 C26 C25 -2.31(18) . . . . ?
C24 C25 C26 N21 -0.67(19) . . . . ?
C12 N11 C27 C24 88.58(14) . . . . ?
C15 N11 C27 C24 -98.82(13) . . . . ?
C25 C24 C27 N11 -10.18(16) . . . . ?
C23 C24 C27 N11 171.55(10) . . . . ?
O32 C31 C32 C33 -13.81(19) . . . . ?
O31 C31 C32 C33 166.86(11) . . . . ?
C31 C32 C33 C33 175.87(12) . . . 2_846 ?

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 0.91(2) 1.77(2) 2.6765(14) 176.3(16) .

_diffrn_measured_fraction_theta_max 0.834
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 1016834'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_A1:Sub

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-2B-21 1,1'-di[(4-pyridyl)methyl]-2,2'-biimidazole, HOOC-(CH2)6-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H16 N6) (C8 H14 O4)
;
_chemical_formula_sum            'C26 H30 N6 O4'
_chemical_formula_weight         490.56

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6196(11)
_cell_length_b                   6.7825(13)
_cell_length_c                   16.078(3)
_cell_angle_alpha                87.236(4)
_cell_angle_beta                 82.669(4)
_cell_angle_gamma                75.451(4)
_cell_volume                     588.22(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4190
_cell_measurement_theta_min      5.69
_cell_measurement_theta_max      32.37

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             260
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9662
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10698
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         32.75
_reflns_number_total             3929
_reflns_number_gt                3433
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0750P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3929
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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 ?

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 0.961(18) 1.700(18) 2.6604(12) 177.3(15) .

_diffrn_measured_fraction_theta_max 0.904
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 1016835'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_A1:Seb

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-2B-22 1,1'-di[(3-pyridyl)methyl]-2,2'-biimidazole, HOOCH-(CH2)8-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H16 N6) (C10 H18 O4)
;
_chemical_formula_sum            'C28 H34 N6 O4'
_chemical_formula_weight         518.61

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6320(7)
_cell_length_b                   6.8450(8)
_cell_length_c                   17.748(2)
_cell_angle_alpha                93.630(7)
_cell_angle_beta                 98.988(7)
_cell_angle_gamma                104.670(7)
_cell_volume                     649.97(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9957
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      67.58

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7876
_exptl_absorpt_correction_T_max  0.9299
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4606
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         68.93
_reflns_number_total             4606
_reflns_number_gt                3942
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4606
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1976
_refine_ls_wR_factor_gt          0.1820
_refine_ls_goodness_of_fit_ref   1.544
_refine_ls_restrained_S_all      1.544
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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 ?

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 1.05(2) 1.63(2) 2.6857(18) 178.1(17) .

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        68.93
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.093
_database_code_depnum_ccdc_archive 'CCDC 1016836'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_A1:Dod

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-2B-23 1,1'-di[(4-pyridyl)methyl]-2,2'-biimidazole, HOOC-(CH2)10-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H16 N6) (C12 H22 O4)
;
_chemical_formula_sum            'C30 H38 N6 O4'
_chemical_formula_weight         546.66

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6047(8)
_cell_length_b                   6.8589(10)
_cell_length_c                   18.879(3)
_cell_angle_alpha                97.644(5)
_cell_angle_beta                 91.164(5)
_cell_angle_gamma                104.659(5)
_cell_volume                     694.80(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6437
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      68.73

_exptl_crystal_description       prism
_exptl_crystal_colour            bronze
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8032
_exptl_absorpt_correction_T_max  0.8584
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9252
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         68.24
_reflns_number_total             2438
_reflns_number_gt                2269
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2438
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1716
_refine_ls_wR_factor_gt          0.1665
_refine_ls_goodness_of_fit_ref   1.472
_refine_ls_restrained_S_all      1.472
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N -0.22222(19) -0.43086(17) 0.06662(6) 0.0265(3) Uani 1 1 d . . .
C12 C -0.1079(2) -0.5443(2) 0.01935(6) 0.0255(4) Uani 1 1 d . . .
N13 N -0.21877(19) -0.74332(17) 0.01395(6) 0.0277(3) Uani 1 1 d . . .
C14 C -0.4097(2) -0.7578(2) 0.05975(7) 0.0280(4) Uani 1 1 d . . .
H14 H -0.5221 -0.8815 0.0673 0.034 Uiso 1 1 calc R . .
C15 C -0.4138(2) -0.5693(2) 0.09248(7) 0.0290(4) Uani 1 1 d . . .
H15 H -0.5263 -0.5386 0.1265 0.035 Uiso 1 1 calc R . .
N21 N 0.4012(2) 0.10751(18) 0.24333(6) 0.0289(3) Uani 1 1 d . . .
C22 C 0.2335(2) 0.1977(2) 0.21965(7) 0.0293(4) Uani 1 1 d . . .
H22 H 0.2475 0.3363 0.2379 0.035 Uiso 1 1 calc R . .
C23 C 0.0411(2) 0.0979(2) 0.16975(7) 0.0291(4) Uani 1 1 d . . .
H23 H -0.0726 0.1675 0.1543 0.035 Uiso 1 1 calc R . .
C24 C 0.0171(2) -0.1069(2) 0.14260(7) 0.0267(4) Uani 1 1 d . . .
C25 C 0.1824(2) -0.2037(2) 0.17004(7) 0.0288(4) Uani 1 1 d . . .
H25 H 0.1664 -0.3444 0.1551 0.035 Uiso 1 1 calc R . .
C26 C 0.3715(2) -0.0916(2) 0.21966(7) 0.0295(4) Uani 1 1 d . . .
H26 H 0.4840 -0.1587 0.2375 0.035 Uiso 1 1 calc R . .
C27 C -0.1803(2) -0.2093(2) 0.08343(7) 0.0278(4) Uani 1 1 d . . .
H27A H -0.3378 -0.1791 0.0975 0.033 Uiso 1 1 calc R . .
H27B H -0.1332 -0.1483 0.0394 0.033 Uiso 1 1 calc R . .
C31 C 0.8011(2) 0.5482(2) 0.32209(7) 0.0283(4) Uani 1 1 d . . .
O31 O 0.79854(19) 0.35345(16) 0.32029(6) 0.0371(3) Uani 1 1 d . . .
H31 H 0.665(4) 0.277(3) 0.2947(10) 0.045 Uiso 1 1 d . . .
O32 O 0.64265(19) 0.60453(16) 0.29145(6) 0.0456(4) Uani 1 1 d . . .
C32 C 1.0217(2) 0.6881(2) 0.36639(7) 0.0291(4) Uani 1 1 d . . .
H32A H 1.1734 0.6759 0.3423 0.035 Uiso 1 1 calc R . .
H32B H 1.0293 0.6405 0.4134 0.035 Uiso 1 1 calc R . .
C33 C 1.0219(2) 0.9124(2) 0.37909(7) 0.0273(4) Uani 1 1 d . . .
H33A H 0.8723 0.9276 0.4039 0.033 Uiso 1 1 calc R . .
H33B H 1.0172 0.9631 0.3325 0.033 Uiso 1 1 calc R . .
C34 C 1.2536(2) 1.0401(2) 0.42464(7) 0.0281(4) Uani 1 1 d . . .
H34A H 1.2581 0.9857 0.4705 0.034 Uiso 1 1 calc R . .
H34B H 1.4016 1.0232 0.3993 0.034 Uiso 1 1 calc R . .
C35 C 1.2682(2) 1.2674(2) 0.44081(7) 0.0282(4) Uani 1 1 d . . .
H35A H 1.1139 1.2848 0.4623 0.034 Uiso 1 1 calc R . .
H35B H 1.2808 1.3256 0.3954 0.034 Uiso 1 1 calc R . .
C36 C 1.4895(2) 1.38577(19) 0.49204(7) 0.0282(4) Uani 1 1 d . . .
H36A H 1.4750 1.3285 0.5377 0.034 Uiso 1 1 calc R . .
H36B H 1.6432 1.3656 0.4709 0.034 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C12 1.3796(17) . ?
N11 C15 1.3861(17) . ?
N11 C27 1.4673(16) . ?
C12 N13 1.3383(17) . ?
C12 C12 1.465(3) 2_545 ?
N13 C14 1.3818(17) . ?
C14 C15 1.363(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C26 1.3461(18) . ?
N21 C22 1.3483(19) . ?
C22 C23 1.3902(19) . ?
C22 H22 0.9500 . ?
C23 C24 1.4014(19) . ?
C23 H23 0.9500 . ?
C24 C25 1.397(2) . ?
C24 C27 1.5210(18) . ?
C25 C26 1.3953(18) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C31 O32 1.2189(18) . ?
C31 O31 1.3277(17) . ?
C31 C32 1.5140(18) . ?
O31 H31 0.89(2) . ?
C32 C33 1.5248(19) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.5399(17) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.5292(19) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.5379(19) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C36 1.530(3) 2_886 ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?

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
_geom_angle_publ_flag
C12 N11 C15 106.11(11) . . ?
C12 N11 C27 130.03(10) . . ?
C15 N11 C27 123.57(10) . . ?
N13 C12 N11 111.32(11) . . ?
N13 C12 C12 124.98(15) . 2_545 ?
N11 C12 C12 123.69(14) . 2_545 ?
C12 N13 C14 105.41(11) . . ?
C15 C14 N13 110.30(12) . . ?
C15 C14 H14 124.8 . . ?
N13 C14 H14 124.8 . . ?
C14 C15 N11 106.86(11) . . ?
C14 C15 H15 126.6 . . ?
N11 C15 H15 126.6 . . ?
C26 N21 C22 117.65(11) . . ?
N21 C22 C23 123.19(12) . . ?
N21 C22 H22 118.4 . . ?
C23 C22 H22 118.4 . . ?
C22 C23 C24 119.08(13) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C25 C24 C23 117.76(12) . . ?
C25 C24 C27 123.63(12) . . ?
C23 C24 C27 118.57(12) . . ?
C26 C25 C24 119.37(13) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
N21 C26 C25 122.80(13) . . ?
N21 C26 H26 118.6 . . ?
C25 C26 H26 118.6 . . ?
N11 C27 C24 115.10(11) . . ?
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 123.12(12) . . ?
O32 C31 C32 124.86(13) . . ?
O31 C31 C32 112.01(12) . . ?
C31 O31 H31 109.3(12) . . ?
C31 C32 C33 115.39(12) . . ?
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 110.93(11) . . ?
C32 C33 H33A 109.5 . . ?
C34 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C34 C33 H33B 109.5 . . ?
H33A C33 H33B 108.0 . . ?
C35 C34 C33 114.61(11) . . ?
C35 C34 H34A 108.6 . . ?
C33 C34 H34A 108.6 . . ?
C35 C34 H34B 108.6 . . ?
C33 C34 H34B 108.6 . . ?
H34A C34 H34B 107.6 . . ?
C34 C35 C36 112.88(12) . . ?
C34 C35 H35A 109.0 . . ?
C36 C35 H35A 109.0 . . ?
C34 C35 H35B 109.0 . . ?
C36 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
C36 C36 C35 113.81(14) 2_886 . ?
C36 C36 H36A 108.8 2_886 . ?
C35 C36 H36A 108.8 . . ?
C36 C36 H36B 108.8 2_886 . ?
C35 C36 H36B 108.8 . . ?
H36A C36 H36B 107.7 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 C12 N13 0.71(14) . . . . ?
C27 N11 C12 N13 -173.07(12) . . . . ?
C15 N11 C12 C12 -179.10(16) . . . 2_545 ?
C27 N11 C12 C12 7.1(2) . . . 2_545 ?
N11 C12 N13 C14 -0.43(14) . . . . ?
C12 C12 N13 C14 179.38(16) 2_545 . . . ?
C12 N13 C14 C15 -0.03(15) . . . . ?
N13 C14 C15 N11 0.46(15) . . . . ?
C12 N11 C15 C14 -0.69(14) . . . . ?
C27 N11 C15 C14 173.59(12) . . . . ?
C26 N21 C22 C23 -3.33(19) . . . . ?
N21 C22 C23 C24 0.4(2) . . . . ?
C22 C23 C24 C25 3.10(18) . . . . ?
C22 C23 C24 C27 -174.82(11) . . . . ?
C23 C24 C25 C26 -3.65(19) . . . . ?
C27 C24 C25 C26 174.16(11) . . . . ?
C22 N21 C26 C25 2.74(19) . . . . ?
C24 C25 C26 N21 0.7(2) . . . . ?
C12 N11 C27 C24 -88.16(16) . . . . ?
C15 N11 C27 C24 99.01(14) . . . . ?
C25 C24 C27 N11 12.28(18) . . . . ?
C23 C24 C27 N11 -169.93(10) . . . . ?
O32 C31 C32 C33 7.3(2) . . . . ?
O31 C31 C32 C33 -172.60(11) . . . . ?
C31 C32 C33 C34 179.93(11) . . . . ?
C32 C33 C34 C35 -179.39(10) . . . . ?
C33 C34 C35 C36 174.69(11) . . . . ?
C34 C35 C36 C36 178.98(12) . . . 2_886 ?

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 0.89(2) 1.80(2) 2.6890(15) 176.6(19) .

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.067
_database_code_depnum_ccdc_archive 'CCDC 1016837'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_A1:Mal

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-2B-24-C 1,1'-di[(4-pyridyl)methyl]-2,2'-biimidazole, HOOC-(CH2)-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H16 N6) (C3 H4 O4)
;
_chemical_formula_sum            'C21 H20 N6 O4'
_chemical_formula_weight         420.43

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.797(3)
_cell_length_b                   4.5097(7)
_cell_length_c                   29.886(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.056(8)
_cell_angle_gamma                90.00
_cell_volume                     1934.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4141
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      29.98

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9636
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20190
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         30.08
_reflns_number_total             5562
_reflns_number_gt                2992
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5562
_refine_ls_number_parameters     308
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1937
_refine_ls_wR_factor_gt          0.1575
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.27117(11) 0.3263(4) 0.18602(5) 0.0303(4) Uani 1 1 d . . .
C12 C 0.27691(14) 0.3470(4) 0.23243(7) 0.0304(5) Uani 1 1 d . . .
N13 N 0.34586(13) 0.1821(4) 0.25655(6) 0.0375(4) Uani 1 1 d . . .
C14 C 0.38466(16) 0.0483(5) 0.22424(8) 0.0416(6) Uani 1 1 d . . .
H14 H 0.4357 -0.0857 0.2312 0.050 Uiso 1 1 calc R . .
C15 C 0.33998(15) 0.1341(5) 0.18138(8) 0.0372(5) Uani 1 1 d . . .
H15 H 0.3536 0.0729 0.1533 0.045 Uiso 1 1 calc R . .
N21 N 0.21673(11) 0.5287(4) 0.29841(5) 0.0307(4) Uani 1 1 d . . .
C22 C 0.21456(14) 0.5263(4) 0.25231(6) 0.0298(5) Uani 1 1 d . A .
N23 N 0.14952(12) 0.7051(4) 0.22900(6) 0.0354(4) Uani 1 1 d . . .
C24 C 0.10930(15) 0.8296(5) 0.26141(7) 0.0383(5) Uani 1 1 d . A .
H24 H 0.0603 0.9710 0.2548 0.046 Uiso 1 1 calc R . .
C25 C 0.14903(15) 0.7236(5) 0.30383(7) 0.0351(5) Uani 1 1 d . A .
H25 H 0.1333 0.7739 0.3319 0.042 Uiso 1 1 calc R . .
N31 N 0.00326(12) -0.1396(4) 0.07473(6) 0.0326(4) Uani 1 1 d . . .
C32 C 0.07376(15) -0.0500(5) 0.05711(7) 0.0372(5) Uani 1 1 d . . .
H32 H 0.0785 -0.1286 0.0283 0.045 Uiso 1 1 calc R . .
C33 C 0.13916(15) 0.1500(5) 0.07899(7) 0.0356(5) Uani 1 1 d . . .
H33 H 0.1873 0.2115 0.0650 0.043 Uiso 1 1 calc R . .
C34 C 0.13495(14) 0.2630(5) 0.12170(7) 0.0295(4) Uani 1 1 d . . .
C35 C 0.06214(14) 0.1688(5) 0.13996(7) 0.0326(5) Uani 1 1 d . . .
H35 H 0.0565 0.2413 0.1690 0.039 Uiso 1 1 calc R . .
C36 C -0.00151(15) -0.0293(5) 0.11586(7) 0.0344(5) Uani 1 1 d . . .
H36 H -0.0511 -0.0914 0.1287 0.041 Uiso 1 1 calc R . .
C37 C 0.20817(15) 0.4740(5) 0.14719(7) 0.0326(5) Uani 1 1 d . . .
H37A H 0.2443 0.5518 0.1259 0.039 Uiso 1 1 calc R . .
H37B H 0.1778 0.6438 0.1586 0.039 Uiso 1 1 calc R . .
N41A N 0.5191(2) 0.6794(7) 0.42207(10) 0.0388(8) Uani 0.766(3) 1 d PD A 1
C42A C 0.4697(2) 0.4630(8) 0.43541(10) 0.0371(7) Uani 0.766(3) 1 d PD A 1
H42A H 0.4918 0.3815 0.4654 0.044 Uiso 0.766(3) 1 calc PR A 1
C43A C 0.3883(2) 0.3521(8) 0.40782(11) 0.0331(7) Uani 0.766(3) 1 d PD A 1
H43A H 0.3556 0.1971 0.4187 0.040 Uiso 0.766(3) 1 calc PR A 1
C44A C 0.3543(4) 0.4699(18) 0.36386(17) 0.0310(9) Uani 0.766(3) 1 d PD A 1
C45A C 0.4084(4) 0.6835(15) 0.34903(14) 0.0357(9) Uani 0.766(3) 1 d PD A 1
H45A H 0.3909 0.7574 0.3184 0.043 Uiso 0.766(3) 1 calc PR A 1
C46A C 0.4877(2) 0.7865(8) 0.37948(12) 0.0381(7) Uani 0.766(3) 1 d PD A 1
H46A H 0.5218 0.9416 0.3696 0.046 Uiso 0.766(3) 1 calc PR A 1
C47A C 0.26984(16) 0.3431(5) 0.33565(7) 0.0377(5) Uani 0.766(3) 1 d P A 1
H47A H 0.2287 0.2894 0.3560 0.045 Uiso 0.766(3) 1 calc PR A 1
H47B H 0.2863 0.1570 0.3219 0.045 Uiso 0.766(3) 1 calc PR A 1
N41B N 0.5342(7) 0.794(2) 0.4055(3) 0.0388(8) Uani 0.234(3) 1 d PD A 2
C42B C 0.4943(9) 0.599(4) 0.4264(5) 0.0371(7) Uani 0.234(3) 1 d PD A 2
H42B H 0.5245 0.5569 0.4576 0.044 Uiso 0.234(3) 1 calc PR A 2
C43B C 0.4126(9) 0.448(3) 0.4081(5) 0.0331(7) Uani 0.234(3) 1 d PD A 2
H43B H 0.3864 0.3143 0.4260 0.040 Uiso 0.234(3) 1 calc PR A 2
C44B C 0.3708(15) 0.504(7) 0.3618(6) 0.0310(9) Uani 0.234(3) 1 d PD A 2
C45B C 0.4069(15) 0.727(6) 0.3389(6) 0.0357(9) Uani 0.234(3) 1 d PD A 2
H45B H 0.3745 0.7916 0.3091 0.043 Uiso 0.234(3) 1 calc PR A 2
C46B C 0.4914(8) 0.851(3) 0.3610(4) 0.0381(7) Uani 0.234(3) 1 d PD A 2
H46B H 0.5209 0.9821 0.3441 0.046 Uiso 0.234(3) 1 calc PR A 2
C47B C 0.26984(16) 0.3431(5) 0.33565(7) 0.0377(5) Uani 0.234(3) 1 d P A 2
H47C H 0.2825 0.1489 0.3230 0.045 Uiso 0.234(3) 1 calc PR A 2
H47D H 0.2325 0.3073 0.3585 0.045 Uiso 0.234(3) 1 calc PR A 2
C51 C -0.17858(15) -0.5905(5) 0.04834(7) 0.0330(5) Uani 1 1 d . . .
O51 O -0.11727(10) -0.4917(3) 0.02689(5) 0.0369(4) Uani 1 1 d . A .
H51 H -0.0848 -0.3588 0.0428 0.044 Uiso 1 1 calc R . .
O52 O -0.17923(11) -0.5253(4) 0.08778(5) 0.0458(4) Uani 1 1 d . A .
C52A C -0.24903(14) -0.7947(5) 0.01875(7) 0.0355(5) Uani 0.766(3) 1 d P A 1
H52A H -0.2901 -0.8755 0.0375 0.043 Uiso 0.766(3) 1 calc PR A 1
H52B H -0.2160 -0.9634 0.0087 0.043 Uiso 0.766(3) 1 calc PR A 1
C53A C -0.3087(2) -0.6411(7) -0.02367(12) 0.0342(7) Uani 0.766(3) 1 d P A 1
O53A O -0.35722(16) -0.4216(5) -0.01186(8) 0.0443(6) Uani 0.766(3) 1 d P A 1
H53A H -0.3956 -0.3580 -0.0354 0.053 Uiso 0.766(3) 1 calc PR A 1
O54A O -0.31222(18) -0.7090(6) -0.06318(8) 0.0477(6) Uani 0.766(3) 1 d P A 1
C52B C -0.24903(14) -0.7947(5) 0.01875(7) 0.0355(5) Uani 0.234(3) 1 d P A 2
H52C H -0.2203 -0.9111 -0.0023 0.043 Uiso 0.234(3) 1 calc PR A 2
H52D H -0.2749 -0.9335 0.0381 0.043 Uiso 0.234(3) 1 calc PR A 2
C53B C -0.3215(9) -0.601(3) -0.0073(4) 0.0342(7) Uani 0.234(3) 1 d P A 2
O53B O -0.3200(7) -0.581(2) -0.0516(4) 0.0477(6) Uani 0.234(3) 1 d P A 2
H53B H -0.3673 -0.4880 -0.0661 0.057 Uiso 0.234(3) 1 calc PR A 2
O54B O -0.3796(5) -0.4887(17) 0.0103(3) 0.0443(6) Uani 0.234(3) 1 d P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C15 1.370(3) . ?
N11 C12 1.372(2) . ?
N11 C37 1.461(3) . ?
C12 N13 1.325(3) . ?
C12 C22 1.458(3) . ?
N13 C14 1.377(3) . ?
C14 C15 1.348(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C22 1.371(2) . ?
N21 C25 1.371(3) . ?
N21 C47A 1.460(3) . ?
C22 N23 1.317(3) . ?
N23 C24 1.374(3) . ?
C24 C25 1.349(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N31 C32 1.340(2) . ?
N31 C36 1.343(2) . ?
C32 C33 1.368(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.390(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.387(3) . ?
C34 C37 1.503(3) . ?
C35 C36 1.369(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
N41A C46A 1.335(4) . ?
N41A C42A 1.337(4) . ?
C42A C43A 1.378(5) . ?
C42A H42A 0.9500 . ?
C43A C44A 1.393(5) . ?
C43A H43A 0.9500 . ?
C44A C45A 1.392(4) . ?
C44A C47A 1.445(5) . ?
C45A C46A 1.380(5) . ?
C45A H45A 0.9500 . ?
C46A H46A 0.9500 . ?
C47A H47A 0.9900 . ?
C47A H47B 0.9900 . ?
N41B C42B 1.298(14) . ?
N41B C46B 1.351(12) . ?
C42B C43B 1.379(14) . ?
C42B H42B 0.9500 . ?
C43B C44B 1.395(15) . ?
C43B H43B 0.9500 . ?
C44B C45B 1.394(15) . ?
C45B C46B 1.382(15) . ?
C45B H45B 0.9500 . ?
C46B H46B 0.9500 . ?
C51 O52 1.217(2) . ?
C51 O51 1.310(2) . ?
C51 C52A 1.506(3) . ?
O51 H51 0.8400 . ?
C52A C53A 1.524(4) . ?
C52A H52A 0.9900 . ?
C52A H52B 0.9900 . ?
C53A O54A 1.209(4) . ?
C53A O53A 1.320(4) . ?
O53A H53A 0.8400 . ?
C53B O54B 1.222(14) . ?
C53B O53B 1.332(12) . ?
O53B H53B 0.8400 . ?

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
_geom_angle_publ_flag
C15 N11 C12 106.28(17) . . ?
C15 N11 C37 123.69(16) . . ?
C12 N11 C37 130.02(16) . . ?
N13 C12 N11 111.24(17) . . ?
N13 C12 C22 124.71(18) . . ?
N11 C12 C22 124.05(18) . . ?
C12 N13 C14 105.17(18) . . ?
C15 C14 N13 110.4(2) . . ?
C15 C14 H14 124.8 . . ?
N13 C14 H14 124.8 . . ?
C14 C15 N11 106.90(18) . . ?
C14 C15 H15 126.6 . . ?
N11 C15 H15 126.6 . . ?
C22 N21 C25 106.52(17) . . ?
C22 N21 C47A 129.69(17) . . ?
C25 N21 C47A 123.42(16) . . ?
N23 C22 N21 111.25(17) . . ?
N23 C22 C12 125.27(17) . . ?
N21 C22 C12 123.48(18) . . ?
C22 N23 C24 105.27(17) . . ?
C25 C24 N23 110.7(2) . . ?
C25 C24 H24 124.7 . . ?
N23 C24 H24 124.7 . . ?
C24 C25 N21 106.28(17) . . ?
C24 C25 H25 126.9 . . ?
N21 C25 H25 126.9 . . ?
C32 N31 C36 117.83(18) . . ?
N31 C32 C33 122.62(18) . . ?
N31 C32 H32 118.7 . . ?
C33 C32 H32 118.7 . . ?
C32 C33 C34 119.77(18) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C35 C34 C33 117.46(19) . . ?
C35 C34 C37 121.86(17) . . ?
C33 C34 C37 120.66(17) . . ?
C36 C35 C34 119.59(18) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
N31 C36 C35 122.71(18) . . ?
N31 C36 H36 118.6 . . ?
C35 C36 H36 118.6 . . ?
N11 C37 C34 110.88(16) . . ?
N11 C37 H37A 109.5 . . ?
C34 C37 H37A 109.5 . . ?
N11 C37 H37B 109.5 . . ?
C34 C37 H37B 109.5 . . ?
H37A C37 H37B 108.1 . . ?
C46A N41A C42A 117.4(3) . . ?
N41A C42A C43A 123.2(3) . . ?
N41A C42A H42A 118.4 . . ?
C43A C42A H42A 118.4 . . ?
C42A C43A C44A 119.3(3) . . ?
C42A C43A H43A 120.4 . . ?
C44A C43A H43A 120.4 . . ?
C45A C44A C43A 117.4(4) . . ?
C45A C44A C47A 124.8(4) . . ?
C43A C44A C47A 117.5(3) . . ?
C46A C45A C44A 119.1(3) . . ?
C46A C45A H45A 120.5 . . ?
C44A C45A H45A 120.5 . . ?
N41A C46A C45A 123.4(3) . . ?
N41A C46A H46A 118.3 . . ?
C45A C46A H46A 118.3 . . ?
C44A C47A N21 116.5(3) . . ?
C44A C47A H47A 108.2 . . ?
N21 C47A H47A 108.2 . . ?
C44A C47A H47B 108.2 . . ?
N21 C47A H47B 108.2 . . ?
H47A C47A H47B 107.3 . . ?
C42B N41B C46B 116.3(11) . . ?
N41B C42B C43B 126.8(13) . . ?
N41B C42B H42B 116.6 . . ?
C43B C42B H42B 116.6 . . ?
C42B C43B C44B 116.0(12) . . ?
C42B C43B H43B 122.0 . . ?
C44B C43B H43B 122.0 . . ?
C45B C44B C43B 119.1(15) . . ?
C46B C45B C44B 117.8(14) . . ?
C46B C45B H45B 121.1 . . ?
C44B C45B H45B 121.1 . . ?
N41B C46B C45B 123.1(11) . . ?
N41B C46B H46B 118.4 . . ?
C45B C46B H46B 118.4 . . ?
O52 C51 O51 124.1(2) . . ?
O52 C51 C52A 123.31(18) . . ?
O51 C51 C52A 112.55(16) . . ?
C51 O51 H51 109.5 . . ?
C51 C52A C53A 112.88(19) . . ?
C51 C52A H52A 109.0 . . ?
C53A C52A H52A 109.0 . . ?
C51 C52A H52B 109.0 . . ?
C53A C52A H52B 109.0 . . ?
H52A C52A H52B 107.8 . . ?
O54A C53A O53A 123.6(3) . . ?
O54A C53A C52A 125.2(3) . . ?
O53A C53A C52A 111.2(3) . . ?
C53A O53A H53A 109.5 . . ?
O54B C53B O53B 125.7(13) . . ?
C53B O53B H53B 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 C12 N13 0.8(2) . . . . ?
C37 N11 C12 N13 -178.20(18) . . . . ?
C15 N11 C12 C22 -178.83(18) . . . . ?
C37 N11 C12 C22 2.1(3) . . . . ?
N11 C12 N13 C14 -0.8(2) . . . . ?
C22 C12 N13 C14 178.82(19) . . . . ?
C12 N13 C14 C15 0.5(2) . . . . ?
N13 C14 C15 N11 0.0(3) . . . . ?
C12 N11 C15 C14 -0.5(2) . . . . ?
C37 N11 C15 C14 178.64(18) . . . . ?
C25 N21 C22 N23 -0.5(2) . . . . ?
C47A N21 C22 N23 172.55(19) . . . . ?
C25 N21 C22 C12 179.54(18) . . . . ?
C47A N21 C22 C12 -7.4(3) . . . . ?
N13 C12 C22 N23 175.58(19) . . . . ?
N11 C12 C22 N23 -4.8(3) . . . . ?
N13 C12 C22 N21 -4.4(3) . . . . ?
N11 C12 C22 N21 175.16(18) . . . . ?
N21 C22 N23 C24 0.8(2) . . . . ?
C12 C22 N23 C24 -179.24(19) . . . . ?
C22 N23 C24 C25 -0.8(2) . . . . ?
N23 C24 C25 N21 0.5(3) . . . . ?
C22 N21 C25 C24 0.0(2) . . . . ?
C47A N21 C25 C24 -173.61(18) . . . . ?
C36 N31 C32 C33 -1.0(3) . . . . ?
N31 C32 C33 C34 1.5(3) . . . . ?
C32 C33 C34 C35 -1.1(3) . . . . ?
C32 C33 C34 C37 177.63(19) . . . . ?
C33 C34 C35 C36 0.3(3) . . . . ?
C37 C34 C35 C36 -178.39(19) . . . . ?
C32 N31 C36 C35 0.1(3) . . . . ?
C34 C35 C36 N31 0.2(3) . . . . ?
C15 N11 C37 C34 76.0(2) . . . . ?
C12 N11 C37 C34 -105.1(2) . . . . ?
C35 C34 C37 N11 72.9(2) . . . . ?
C33 C34 C37 N11 -105.8(2) . . . . ?
C46A N41A C42A C43A -1.3(4) . . . . ?
N41A C42A C43A C44A -0.4(6) . . . . ?
C42A C43A C44A C45A 3.9(10) . . . . ?
C42A C43A C44A C47A 178.7(4) . . . . ?
C43A C44A C45A C46A -5.6(12) . . . . ?
C47A C44A C45A C46A -180.0(6) . . . . ?
C42A N41A C46A C45A -0.6(6) . . . . ?
C44A C45A C46A N41A 4.1(10) . . . . ?
C45A C44A C47A N21 -27.7(10) . . . . ?
C43A C44A C47A N21 157.9(5) . . . . ?
C22 N21 C47A C44A 99.2(4) . . . . ?
C25 N21 C47A C44A -88.8(4) . . . . ?
C46B N41B C42B C43B -1(2) . . . . ?
N41B C42B C43B C44B 2(3) . . . . ?
C42B C43B C44B C45B -7(4) . . . . ?
C43B C44B C45B C46B 10(5) . . . . ?
C42B N41B C46B C45B 4(2) . . . . ?
C44B C45B C46B N41B -9(4) . . . . ?
O52 C51 C52A C53A 116.5(2) . . . . ?
O51 C51 C52A C53A -63.4(2) . . . . ?
C51 C52A C53A O54A 118.9(3) . . . . ?
C51 C52A C53A O53A -61.3(3) . . . . ?

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
O51 H51 N31 0.84 1.73 2.551(2) 166.5 .
O53A H53A N41A 0.84 1.75 2.586(4) 169.9 4_465
O53B H53B N41B 0.84 1.74 2.576(16) 178.3 4_465

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.067
_database_code_depnum_ccdc_archive 'CCDC 1016838'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_A1:Glu

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-2B-25-SE 1,1'-di[(4-pyridyl)methyl]-2,2'-biimidazole, (HOOC-(CH2)3-COOH)2
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H16 N6) (C5 H8 O4)2
;
_chemical_formula_sum            'C28 H32 N6 O8'
_chemical_formula_weight         580.60

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6142(11)
_cell_length_b                   8.6608(13)
_cell_length_c                   11.0348(16)
_cell_angle_alpha                102.357(5)
_cell_angle_beta                 105.996(5)
_cell_angle_gamma                93.866(5)
_cell_volume                     677.09(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      32.57

_exptl_crystal_description       prism
_exptl_crystal_colour            bronze
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             306
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9547
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17551
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         32.68
_reflns_number_total             4555
_reflns_number_gt                4015
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4555
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.62007(10) -0.07810(9) 0.14224(7) 0.01813(14) Uani 1 1 d . . .
C12 C 0.59062(11) -0.00993(10) 0.03860(8) 0.01752(16) Uani 1 1 d . . .
N13 N 0.74821(10) 0.03259(9) 0.01722(7) 0.02097(16) Uani 1 1 d . . .
C14 C 0.88328(12) -0.00848(11) 0.11157(9) 0.02223(18) Uani 1 1 d . . .
H14 H 1.0115 0.0079 0.1212 0.027 Uiso 1 1 calc R . .
C15 C 0.80773(12) -0.07603(11) 0.18939(9) 0.02077(17) Uani 1 1 d . . .
H15 H 0.8716 -0.1141 0.2617 0.025 Uiso 1 1 calc R . .
N21 N 0.34290(11) 0.23526(9) 0.47119(8) 0.02235(16) Uani 1 1 d . . .
C22 C 0.48093(13) 0.26575(11) 0.42259(9) 0.02372(18) Uani 1 1 d . . .
H22 H 0.5458 0.3707 0.4493 0.028 Uiso 1 1 calc R . .
C23 C 0.53381(13) 0.15204(10) 0.33550(9) 0.02138(17) Uani 1 1 d . . .
H23 H 0.6320 0.1789 0.3030 0.026 Uiso 1 1 calc R . .
C24 C 0.44088(11) -0.00156(10) 0.29676(8) 0.01697(15) Uani 1 1 d . . .
C25 C 0.29974(12) -0.03482(10) 0.34897(8) 0.02011(17) Uani 1 1 d . . .
H25 H 0.2350 -0.1395 0.3260 0.024 Uiso 1 1 calc R . .
C26 C 0.25506(12) 0.08604(11) 0.43446(9) 0.02183(17) Uani 1 1 d . . .
H26 H 0.1577 0.0623 0.4688 0.026 Uiso 1 1 calc R . .
C27 C 0.48843(12) -0.13347(10) 0.20283(8) 0.01947(16) Uani 1 1 d . . .
H27A H 0.5404 -0.2135 0.2495 0.023 Uiso 1 1 calc R . .
H27B H 0.3740 -0.1869 0.1340 0.023 Uiso 1 1 calc R . .
C31 C 0.07456(12) 0.42435(10) 0.64038(8) 0.02010(17) Uani 1 1 d . . .
O31 O 0.21847(10) 0.47089(9) 0.60585(8) 0.02933(17) Uani 1 1 d . . .
H31 H 0.259(2) 0.3801(18) 0.5604(15) 0.035 Uiso 1 1 d . . .
O32 O 0.00288(10) 0.28694(8) 0.61021(7) 0.02753(16) Uani 1 1 d . . .
C32 C 0.01185(13) 0.55953(10) 0.72141(9) 0.02116(17) Uani 1 1 d . . .
H32A H -0.0385 0.6329 0.6670 0.025 Uiso 1 1 calc R . .
H32B H 0.1195 0.6200 0.7932 0.025 Uiso 1 1 calc R . .
C33 C -0.13427(13) 0.50327(11) 0.77832(9) 0.02256(18) Uani 1 1 d . . .
H33A H -0.0919 0.4180 0.8220 0.027 Uiso 1 1 calc R . .
H33B H -0.2495 0.4580 0.7074 0.027 Uiso 1 1 calc R . .
C34 C -0.17279(14) 0.64054(11) 0.87603(10) 0.02430(18) Uani 1 1 d . . .
H34A H -0.0573 0.6873 0.9463 0.029 Uiso 1 1 calc R . .
H34B H -0.2180 0.7249 0.8321 0.029 Uiso 1 1 calc R . .
C35 C -0.31430(13) 0.58195(11) 0.93311(9) 0.02252(18) Uani 1 1 d . . .
O35 O -0.47807(11) 0.61987(11) 0.88919(9) 0.03519(19) Uani 1 1 d . . .
H35 H -0.554(2) 0.5790(19) 0.9213(16) 0.042 Uiso 1 1 d . . .
O36 O -0.27839(11) 0.50049(11) 1.01252(9) 0.0368(2) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C12 1.3684(11) . ?
N11 C15 1.3768(11) . ?
N11 C27 1.4572(10) . ?
C12 N13 1.3284(11) . ?
C12 C12 1.4513(17) 2_655 ?
N13 C14 1.3733(12) . ?
C14 C15 1.3610(12) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C26 1.3386(12) . ?
N21 C22 1.3399(11) . ?
C22 C23 1.3846(12) . ?
C22 H22 0.9500 . ?
C23 C24 1.3842(12) . ?
C23 H23 0.9500 . ?
C24 C25 1.3929(11) . ?
C24 C27 1.5055(11) . ?
C25 C26 1.3797(12) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C31 O32 1.2115(11) . ?
C31 O31 1.3208(11) . ?
C31 C32 1.5036(12) . ?
O31 H31 0.958(15) . ?
C32 C33 1.5207(12) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.5279(12) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.5008(12) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 O36 1.2243(12) . ?
C35 O35 1.2993(12) . ?
O35 H35 0.851(17) . ?

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
_geom_angle_publ_flag
C12 N11 C15 106.67(7) . . ?
C12 N11 C27 129.44(7) . . ?
C15 N11 C27 123.74(7) . . ?
N13 C12 N11 111.27(7) . . ?
N13 C12 C12 124.91(10) . 2_655 ?
N11 C12 C12 123.81(9) . 2_655 ?
C12 N13 C14 105.36(7) . . ?
C15 C14 N13 110.50(8) . . ?
C15 C14 H14 124.7 . . ?
N13 C14 H14 124.7 . . ?
C14 C15 N11 106.19(8) . . ?
C14 C15 H15 126.9 . . ?
N11 C15 H15 126.9 . . ?
C26 N21 C22 117.57(7) . . ?
N21 C22 C23 123.36(8) . . ?
N21 C22 H22 118.3 . . ?
C23 C22 H22 118.3 . . ?
C24 C23 C22 118.73(8) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C25 118.18(8) . . ?
C23 C24 C27 122.69(7) . . ?
C25 C24 C27 119.12(7) . . ?
C26 C25 C24 119.26(8) . . ?
C26 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
N21 C26 C25 122.87(8) . . ?
N21 C26 H26 118.6 . . ?
C25 C26 H26 118.6 . . ?
N11 C27 C24 113.35(7) . . ?
N11 C27 H27A 108.9 . . ?
C24 C27 H27A 108.9 . . ?
N11 C27 H27B 108.9 . . ?
C24 C27 H27B 108.9 . . ?
H27A C27 H27B 107.7 . . ?
O32 C31 O31 123.07(8) . . ?
O32 C31 C32 124.20(8) . . ?
O31 C31 C32 112.73(8) . . ?
C31 O31 H31 109.8(9) . . ?
C31 C32 C33 112.83(7) . . ?
C31 C32 H32A 109.0 . . ?
C33 C32 H32A 109.0 . . ?
C31 C32 H32B 109.0 . . ?
C33 C32 H32B 109.0 . . ?
H32A C32 H32B 107.8 . . ?
C32 C33 C34 111.13(7) . . ?
C32 C33 H33A 109.4 . . ?
C34 C33 H33A 109.4 . . ?
C32 C33 H33B 109.4 . . ?
C34 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
C35 C34 C33 110.32(7) . . ?
C35 C34 H34A 109.6 . . ?
C33 C34 H34A 109.6 . . ?
C35 C34 H34B 109.6 . . ?
C33 C34 H34B 109.6 . . ?
H34A C34 H34B 108.1 . . ?
O36 C35 O35 122.72(9) . . ?
O36 C35 C34 122.10(9) . . ?
O35 C35 C34 115.14(9) . . ?
C35 O35 H35 111.1(11) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 C12 N13 0.82(9) . . . . ?
C27 N11 C12 N13 176.42(8) . . . . ?
C15 N11 C12 C12 179.79(10) . . . 2_655 ?
C27 N11 C12 C12 -4.61(15) . . . 2_655 ?
N11 C12 N13 C14 -0.63(10) . . . . ?
C12 C12 N13 C14 -179.59(10) 2_655 . . . ?
C12 N13 C14 C15 0.20(10) . . . . ?
N13 C14 C15 N11 0.29(10) . . . . ?
C12 N11 C15 C14 -0.65(9) . . . . ?
C27 N11 C15 C14 -176.56(7) . . . . ?
C26 N21 C22 C23 1.18(15) . . . . ?
N21 C22 C23 C24 -0.44(15) . . . . ?
C22 C23 C24 C25 -0.87(13) . . . . ?
C22 C23 C24 C27 -179.84(8) . . . . ?
C23 C24 C25 C26 1.40(13) . . . . ?
C27 C24 C25 C26 -179.60(8) . . . . ?
C22 N21 C26 C25 -0.62(14) . . . . ?
C24 C25 C26 N21 -0.67(14) . . . . ?
C12 N11 C27 C24 -81.37(11) . . . . ?
C15 N11 C27 C24 93.56(10) . . . . ?
C23 C24 C27 N11 -9.03(12) . . . . ?
C25 C24 C27 N11 172.02(7) . . . . ?
O32 C31 C32 C33 8.18(13) . . . . ?
O31 C31 C32 C33 -171.29(8) . . . . ?
C31 C32 C33 C34 171.35(8) . . . . ?
C32 C33 C34 C35 -178.81(8) . . . . ?
C33 C34 C35 O36 73.35(12) . . . . ?
C33 C34 C35 O35 -104.65(10) . . . . ?

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 0.958(15) 1.695(15) 2.6475(10) 172.9(14) .
O35 H35 O36 0.851(17) 1.802(17) 2.6520(11) 177.3(16) 2_467

_diffrn_measured_fraction_theta_max 0.917
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 1016839'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_A3:Adi

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-2B-2 1,1'-di[(2-pyridyl)methyl]-2,2'-biimidazole, HOOC-(CH2)4-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H16 N6) (C6 H10 O4)
;
_chemical_formula_sum            'C24 H26 N6 O4'
_chemical_formula_weight         462.51

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0121(5)
_cell_length_b                   7.8964(8)
_cell_length_c                   15.1589(16)
_cell_angle_alpha                78.403(4)
_cell_angle_beta                 88.333(4)
_cell_angle_gamma                72.636(3)
_cell_volume                     560.62(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7606
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      32.14

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9662
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12569
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         32.01
_reflns_number_total             3713
_reflns_number_gt                3150
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0650P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3713
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1317
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.41957(16) 0.48192(10) 0.38319(5) 0.02268(16) Uani 1 1 d . . .
C12 C 0.43897(18) 0.45066(12) 0.47517(6) 0.02271(18) Uani 1 1 d . . .
N13 N 0.32930(19) 0.32138(12) 0.51192(6) 0.02979(19) Uani 1 1 d . . .
C14 C 0.2333(2) 0.26950(15) 0.44114(8) 0.0326(2) Uani 1 1 d . . .
H14 H 0.1430 0.1780 0.4469 0.039 Uiso 1 1 calc R . .
C15 C 0.2851(2) 0.36711(13) 0.36166(7) 0.0281(2) Uani 1 1 d . . .
H15 H 0.2377 0.3578 0.3030 0.034 Uiso 1 1 calc R . .
N21 N 0.39182(17) 0.90124(11) 0.22234(6) 0.02602(17) Uani 1 1 d . . .
C22 C 0.31760(17) 0.79269(12) 0.29184(6) 0.02130(17) Uani 1 1 d . . .
C23 C 0.07398(19) 0.84941(13) 0.33724(7) 0.02697(19) Uani 1 1 d . . .
H23 H 0.0255 0.7692 0.3861 0.032 Uiso 1 1 calc R . .
C24 C -0.0979(2) 1.02527(15) 0.31011(8) 0.0333(2) Uani 1 1 d . . .
H24 H -0.2665 1.0673 0.3402 0.040 Uiso 1 1 calc R . .
C25 C -0.0221(2) 1.13827(14) 0.23928(8) 0.0356(2) Uani 1 1 d . . .
H25 H -0.1359 1.2597 0.2196 0.043 Uiso 1 1 calc R . .
C26 C 0.2237(2) 1.07065(14) 0.19747(8) 0.0331(2) Uani 1 1 d . . .
H26 H 0.2762 1.1486 0.1484 0.040 Uiso 1 1 calc R . .
C27 C 0.52032(19) 0.60568(12) 0.31630(6) 0.02475(19) Uani 1 1 d . . .
H27A H 0.5624 0.5548 0.2611 0.030 Uiso 1 1 calc R . .
H27B H 0.6972 0.6146 0.3395 0.030 Uiso 1 1 calc R . .
C31 C 0.9888(2) 0.69536(14) 0.10852(6) 0.02665(19) Uani 1 1 d . . .
O31 O 0.81815(17) 0.85843(11) 0.10722(6) 0.0371(2) Uani 1 1 d . . .
H31 H 0.685(3) 0.856(2) 0.1500(11) 0.045 Uiso 1 1 d . . .
O32 O 0.9680(2) 0.56203(12) 0.15970(6) 0.0455(2) Uani 1 1 d . . .
C32 C 1.2118(2) 0.69137(14) 0.03986(7) 0.0300(2) Uani 1 1 d . . .
H32A H 1.3323 0.7620 0.0541 0.036 Uiso 1 1 calc R . .
H32B H 1.1219 0.7508 -0.0203 0.036 Uiso 1 1 calc R . .
C33 C 1.3925(2) 0.50148(14) 0.03626(7) 0.0283(2) Uani 1 1 d . . .
H33A H 1.2713 0.4290 0.0249 0.034 Uiso 1 1 calc R . .
H33B H 1.4902 0.4441 0.0955 0.034 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C12 1.3673(11) . ?
N11 C15 1.3710(13) . ?
N11 C27 1.4507(11) . ?
C12 N13 1.3203(12) . ?
C12 C12 1.4476(18) 2_666 ?
N13 C14 1.3693(14) . ?
C14 C15 1.3569(15) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C26 1.3359(13) . ?
N21 C22 1.3369(11) . ?
C22 C23 1.3834(12) . ?
C22 C27 1.5023(12) . ?
C23 C24 1.3844(14) . ?
C23 H23 0.9500 . ?
C24 C25 1.3736(17) . ?
C24 H24 0.9500 . ?
C25 C26 1.3793(17) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C31 O32 1.2056(12) . ?
C31 O31 1.3129(13) . ?
C31 C32 1.5026(13) . ?
O31 H31 0.920(17) . ?
C32 C33 1.5137(15) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C33 1.5152(18) 2_865 ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

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
_geom_angle_publ_flag
C12 N11 C15 106.74(8) . . ?
C12 N11 C27 129.92(8) . . ?
C15 N11 C27 123.33(8) . . ?
N13 C12 N11 111.16(8) . . ?
N13 C12 C12 124.99(10) . 2_666 ?
N11 C12 C12 123.85(10) . 2_666 ?
C12 N13 C14 105.48(8) . . ?
C15 C14 N13 110.52(9) . . ?
C15 C14 H14 124.7 . . ?
N13 C14 H14 124.7 . . ?
C14 C15 N11 106.09(9) . . ?
C14 C15 H15 127.0 . . ?
N11 C15 H15 127.0 . . ?
C26 N21 C22 117.94(9) . . ?
N21 C22 C23 122.34(8) . . ?
N21 C22 C27 114.51(8) . . ?
C23 C22 C27 123.15(8) . . ?
C22 C23 C24 118.78(9) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C25 C24 C23 119.29(10) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 118.21(9) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
N21 C26 C25 123.44(10) . . ?
N21 C26 H26 118.3 . . ?
C25 C26 H26 118.3 . . ?
N11 C27 C22 113.90(7) . . ?
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 123.23(9) . . ?
O32 C31 C32 123.40(10) . . ?
O31 C31 C32 113.37(8) . . ?
C31 O31 H31 111.1(10) . . ?
C31 C32 C33 113.11(8) . . ?
C31 C32 H32A 109.0 . . ?
C33 C32 H32A 109.0 . . ?
C31 C32 H32B 109.0 . . ?
C33 C32 H32B 109.0 . . ?
H32A C32 H32B 107.8 . . ?
C32 C33 C33 112.65(10) . 2_865 ?
C32 C33 H33A 109.1 . . ?
C33 C33 H33A 109.1 2_865 . ?
C32 C33 H33B 109.1 . . ?
C33 C33 H33B 109.1 2_865 . ?
H33A C33 H33B 107.8 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 C12 N13 1.12(10) . . . . ?
C27 N11 C12 N13 -177.55(9) . . . . ?
C15 N11 C12 C12 -178.09(11) . . . 2_666 ?
C27 N11 C12 C12 3.23(17) . . . 2_666 ?
N11 C12 N13 C14 -0.74(11) . . . . ?
C12 C12 N13 C14 178.47(11) 2_666 . . . ?
C12 N13 C14 C15 0.07(12) . . . . ?
N13 C14 C15 N11 0.60(12) . . . . ?
C12 N11 C15 C14 -1.01(11) . . . . ?
C27 N11 C15 C14 177.77(8) . . . . ?
C26 N21 C22 C23 0.77(14) . . . . ?
C26 N21 C22 C27 -179.06(9) . . . . ?
N21 C22 C23 C24 -0.49(15) . . . . ?
C27 C22 C23 C24 179.32(9) . . . . ?
C22 C23 C24 C25 -0.11(16) . . . . ?
C23 C24 C25 C26 0.38(17) . . . . ?
C22 N21 C26 C25 -0.47(16) . . . . ?
C24 C25 C26 N21 -0.10(17) . . . . ?
C12 N11 C27 C22 -87.55(11) . . . . ?
C15 N11 C27 C22 93.96(11) . . . . ?
N21 C22 C27 N11 -171.89(8) . . . . ?
C23 C22 C27 N11 8.29(13) . . . . ?
O32 C31 C32 C33 4.75(15) . . . . ?
O31 C31 C32 C33 -175.10(9) . . . . ?
C31 C32 C33 C33 177.22(10) . . . 2_865 ?

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 0.920(17) 1.798(17) 2.7046(12) 167.7(15) .

_diffrn_measured_fraction_theta_max 0.950
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 1016840'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_A3:Sub

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-2B-3 1,1'-di[(2-pyridyl)methyl]-2,2'-biimidazole, HOOC-(CH2)6-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H16 N6) (C8 H14 O4)
;
_chemical_formula_sum            'C26 H30 N6 O4'
_chemical_formula_weight         490.56

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.1024(10)
_cell_length_b                   8.0128(15)
_cell_length_c                   16.497(3)
_cell_angle_alpha                99.940(9)
_cell_angle_beta                 93.967(10)
_cell_angle_gamma                108.231(8)
_cell_volume                     625.5(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5256
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      65.62

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             260
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7983
_exptl_absorpt_correction_T_max  0.8666
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9109
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         66.73
_reflns_number_total             2111
_reflns_number_gt                1891
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2111
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1580
_refine_ls_wR_factor_gt          0.1457
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_restrained_S_all      1.176
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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 ?

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 0.96(3) 1.78(3) 2.722(2) 167(2) .

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        66.73
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 1016841'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_A3:Seb

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-2B-4 1,1'-di[(2-pyridyl)methyl]-2,2'-biimidazole, HOOC-(CH2)8-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H16 N6) (C10 H18 O4)
;
_chemical_formula_sum            'C28 H34 N6 O4'
_chemical_formula_weight         518.61

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.2731(8)
_cell_length_b                   7.8464(11)
_cell_length_c                   17.163(3)
_cell_angle_alpha                81.964(6)
_cell_angle_beta                 88.938(6)
_cell_angle_gamma                72.499(6)
_cell_volume                     670.38(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7056
_cell_measurement_theta_min      5.21
_cell_measurement_theta_max      66.89

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8035
_exptl_absorpt_correction_T_max  0.9065
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11734
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.21
_diffrn_reflns_theta_max         67.90
_reflns_number_total             2326
_reflns_number_gt                2145
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2326
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0850
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.56828(19) 0.59508(13) 0.39717(5) 0.0220(2) Uani 1 1 d . . .
C12 C 0.5577(2) 0.56611(15) 0.47824(7) 0.0221(3) Uani 1 1 d . . .
N13 N 0.6683(2) 0.67227(14) 0.51101(6) 0.0278(2) Uani 1 1 d . . .
C14 C 0.7556(3) 0.77061(17) 0.44862(8) 0.0297(3) Uani 1 1 d . . .
H14 H 0.8436 0.8580 0.4537 0.036 Uiso 1 1 calc R . .
C15 C 0.6976(2) 0.72438(16) 0.37873(7) 0.0262(3) Uani 1 1 d . . .
H15 H 0.7380 0.7717 0.3276 0.031 Uiso 1 1 calc R . .
N21 N 0.58920(19) 0.27407(13) 0.25603(6) 0.0233(2) Uani 1 1 d . . .
C22 C 0.6664(2) 0.34089(15) 0.31707(6) 0.0203(3) Uani 1 1 d . . .
C23 C 0.9108(2) 0.25765(16) 0.35687(7) 0.0243(3) Uani 1 1 d . . .
H23 H 0.9608 0.3076 0.3993 0.029 Uiso 1 1 calc R . .
C24 C 1.0800(2) 0.10032(17) 0.33342(8) 0.0288(3) Uani 1 1 d . . .
H24 H 1.2473 0.0420 0.3595 0.035 Uiso 1 1 calc R . .
C25 C 1.0006(3) 0.02987(17) 0.27135(8) 0.0303(3) Uani 1 1 d . . .
H25 H 1.1113 -0.0776 0.2544 0.036 Uiso 1 1 calc R . .
C26 C 0.7545(3) 0.12115(17) 0.23480(7) 0.0280(3) Uani 1 1 d . . .
H26 H 0.7000 0.0729 0.1925 0.034 Uiso 1 1 calc R . .
C27 C 0.4669(2) 0.51194(16) 0.33784(7) 0.0231(3) Uani 1 1 d . . .
H27A H 0.4153 0.6004 0.2894 0.028 Uiso 1 1 calc R . .
H27B H 0.3050 0.4833 0.3578 0.028 Uiso 1 1 calc R . .
C31 C -0.0252(2) 0.54231(15) 0.15652(7) 0.0216(3) Uani 1 1 d . . .
O31 O 0.17061(17) 0.39039(12) 0.15068(5) 0.0298(2) Uani 1 1 d . . .
H31 H 0.293(3) 0.370(2) 0.1901(10) 0.036 Uiso 1 1 d . . .
O32 O -0.02729(17) 0.63900(12) 0.20646(5) 0.0295(2) Uani 1 1 d . . .
C32 C -0.2416(2) 0.58204(16) 0.09348(7) 0.0234(3) Uani 1 1 d . . .
H32A H -0.3128 0.4781 0.0971 0.028 Uiso 1 1 calc R . .
H32B H -0.1616 0.5943 0.0411 0.028 Uiso 1 1 calc R . .
C33 C -0.4720(2) 0.75304(16) 0.09948(7) 0.0231(3) Uani 1 1 d . . .
H33A H -0.3996 0.8549 0.1021 0.028 Uiso 1 1 calc R . .
H33B H -0.5668 0.7354 0.1489 0.028 Uiso 1 1 calc R . .
C34 C -0.6705(2) 0.80185(16) 0.02968(7) 0.0232(3) Uani 1 1 d . . .
H34A H -0.5755 0.8195 -0.0197 0.028 Uiso 1 1 calc R . .
H34B H -0.7425 0.6999 0.0270 0.028 Uiso 1 1 calc R . .
C35 C -0.9020(2) 0.97296(16) 0.03533(7) 0.0238(3) Uani 1 1 d . . .
H35A H -0.8293 1.0738 0.0398 0.029 Uiso 1 1 calc R . .
H35B H -0.9999 0.9537 0.0839 0.029 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C12 1.3810(15) . ?
N11 C15 1.3830(16) . ?
N11 C27 1.4708(14) . ?
C12 N13 1.3363(15) . ?
C12 C12 1.466(2) 2_666 ?
N13 C14 1.3852(17) . ?
C14 C15 1.3661(18) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C26 1.3467(16) . ?
N21 C22 1.3549(15) . ?
C22 C23 1.3983(17) . ?
C22 C27 1.5184(16) . ?
C23 C24 1.3947(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.3916(19) . ?
C24 H24 0.9500 . ?
C25 C26 1.3914(19) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C31 O32 1.2193(14) . ?
C31 O31 1.3365(14) . ?
C31 C32 1.5190(16) . ?
O31 H31 0.906(17) . ?
C32 C33 1.5300(16) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.5343(16) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.5327(17) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C35 1.535(2) 2_375 ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?

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
_geom_angle_publ_flag
C12 N11 C15 106.65(10) . . ?
C12 N11 C27 129.73(10) . . ?
C15 N11 C27 123.62(10) . . ?
N13 C12 N11 111.14(10) . . ?
N13 C12 C12 125.07(13) . 2_666 ?
N11 C12 C12 123.79(13) . 2_666 ?
C12 N13 C14 105.32(10) . . ?
C15 C14 N13 110.51(11) . . ?
C15 C14 H14 124.7 . . ?
N13 C14 H14 124.7 . . ?
C14 C15 N11 106.37(11) . . ?
C14 C15 H15 126.8 . . ?
N11 C15 H15 126.8 . . ?
C26 N21 C22 117.91(10) . . ?
N21 C22 C23 122.05(11) . . ?
N21 C22 C27 114.48(10) . . ?
C23 C22 C27 123.47(10) . . ?
C24 C23 C22 119.10(11) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C25 C24 C23 119.13(11) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C26 C25 C24 118.16(11) . . ?
C26 C25 H25 120.9 . . ?
C24 C25 H25 120.9 . . ?
N21 C26 C25 123.65(11) . . ?
N21 C26 H26 118.2 . . ?
C25 C26 H26 118.2 . . ?
N11 C27 C22 113.57(9) . . ?
N11 C27 H27A 108.9 . . ?
C22 C27 H27A 108.9 . . ?
N11 C27 H27B 108.9 . . ?
C22 C27 H27B 108.9 . . ?
H27A C27 H27B 107.7 . . ?
O32 C31 O31 123.50(10) . . ?
O32 C31 C32 123.96(10) . . ?
O31 C31 C32 112.53(10) . . ?
C31 O31 H31 109.7(10) . . ?
C31 C32 C33 113.93(9) . . ?
C31 C32 H32A 108.8 . . ?
C33 C32 H32A 108.8 . . ?
C31 C32 H32B 108.8 . . ?
C33 C32 H32B 108.8 . . ?
H32A C32 H32B 107.7 . . ?
C32 C33 C34 112.69(9) . . ?
C32 C33 H33A 109.1 . . ?
C34 C33 H33A 109.1 . . ?
C32 C33 H33B 109.1 . . ?
C34 C33 H33B 109.1 . . ?
H33A C33 H33B 107.8 . . ?
C35 C34 C33 112.98(9) . . ?
C35 C34 H34A 109.0 . . ?
C33 C34 H34A 109.0 . . ?
C35 C34 H34B 109.0 . . ?
C33 C34 H34B 109.0 . . ?
H34A C34 H34B 107.8 . . ?
C34 C35 C35 113.66(12) . 2_375 ?
C34 C35 H35A 108.8 . . ?
C35 C35 H35A 108.8 2_375 . ?
C34 C35 H35B 108.8 . . ?
C35 C35 H35B 108.8 2_375 . ?
H35A C35 H35B 107.7 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 C12 N13 1.18(13) . . . . ?
C27 N11 C12 N13 -178.60(10) . . . . ?
C15 N11 C12 C12 -178.12(13) . . . 2_666 ?
C27 N11 C12 C12 2.1(2) . . . 2_666 ?
N11 C12 N13 C14 -0.81(13) . . . . ?
C12 C12 N13 C14 178.47(14) 2_666 . . . ?
C12 N13 C14 C15 0.14(14) . . . . ?
N13 C14 C15 N11 0.57(14) . . . . ?
C12 N11 C15 C14 -1.03(13) . . . . ?
C27 N11 C15 C14 178.77(10) . . . . ?
C26 N21 C22 C23 0.99(17) . . . . ?
C26 N21 C22 C27 -179.18(10) . . . . ?
N21 C22 C23 C24 -0.40(17) . . . . ?
C27 C22 C23 C24 179.79(11) . . . . ?
C22 C23 C24 C25 -0.33(18) . . . . ?
C23 C24 C25 C26 0.44(18) . . . . ?
C22 N21 C26 C25 -0.88(18) . . . . ?
C24 C25 C26 N21 0.17(19) . . . . ?
C12 N11 C27 C22 -89.43(14) . . . . ?
C15 N11 C27 C22 90.82(13) . . . . ?
N21 C22 C27 N11 -172.53(9) . . . . ?
C23 C22 C27 N11 7.29(16) . . . . ?
O32 C31 C32 C33 -2.08(16) . . . . ?
O31 C31 C32 C33 178.76(10) . . . . ?
C31 C32 C33 C34 173.22(9) . . . . ?
C32 C33 C34 C35 179.96(9) . . . . ?
C33 C34 C35 C35 178.21(12) . . . 2_375 ?

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 0.906(17) 1.847(17) 2.7294(13) 163.9(14) .

_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.957
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 1016842'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_A3:Dod

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-2B-5 1,1'-di[(2-pyridyl)methyl]-2,2'-biimidazole, HOOC-(CH2)10-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H16 N6) (C12 H22 O4)
;
_chemical_formula_sum            'C30 H38 N6 O4'
_chemical_formula_weight         546.66

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.2955(8)
_cell_length_b                   7.8185(13)
_cell_length_c                   18.424(3)
_cell_angle_alpha                85.042(10)
_cell_angle_beta                 83.543(10)
_cell_angle_gamma                71.912(10)
_cell_volume                     719.4(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4754
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      66.72

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8299
_exptl_absorpt_correction_T_max  0.8974
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11812
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         68.34
_reflns_number_total             2493
_reflns_number_gt                2079
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2493
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1335
_refine_ls_wR_factor_gt          0.1244
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N -0.1090(3) 0.4262(2) 0.09542(8) 0.0214(4) Uani 1 1 d . . .
C12 C -0.0669(4) 0.4384(2) 0.02012(9) 0.0212(4) Uani 1 1 d . . .
N13 N -0.1637(3) 0.3252(2) -0.01038(9) 0.0277(4) Uani 1 1 d . . .
C14 C -0.2764(4) 0.2399(3) 0.04762(11) 0.0303(5) Uani 1 1 d . . .
H14 H -0.3623 0.1518 0.0429 0.036 Uiso 1 1 calc R . .
C15 C -0.2462(4) 0.3008(3) 0.11255(10) 0.0265(4) Uani 1 1 d . . .
H15 H -0.3072 0.2644 0.1601 0.032 Uiso 1 1 calc R . .
N21 N -0.1862(3) 0.7771(2) 0.22668(8) 0.0229(4) Uani 1 1 d . . .
C22 C -0.2398(4) 0.6978(2) 0.17005(9) 0.0199(4) Uani 1 1 d . . .
C23 C -0.4689(4) 0.7731(3) 0.13338(10) 0.0242(4) Uani 1 1 d . . .
H23 H -0.5022 0.7140 0.0942 0.029 Uiso 1 1 calc R . .
C24 C -0.6474(4) 0.9360(3) 0.15518(11) 0.0292(5) Uani 1 1 d . . .
H24 H -0.8047 0.9897 0.1310 0.035 Uiso 1 1 calc R . .
C25 C -0.5935(4) 1.0195(3) 0.21275(11) 0.0304(5) Uani 1 1 d . . .
H25 H -0.7119 1.1312 0.2284 0.037 Uiso 1 1 calc R . .
C26 C -0.3619(4) 0.9351(3) 0.24662(11) 0.0279(4) Uani 1 1 d . . .
H26 H -0.3253 0.9919 0.2860 0.034 Uiso 1 1 calc R . .
C27 C -0.0317(4) 0.5216(3) 0.15077(9) 0.0234(4) Uani 1 1 d . . .
H27A H 0.1373 0.5461 0.1322 0.028 Uiso 1 1 calc R . .
H27B H 0.0017 0.4421 0.1957 0.028 Uiso 1 1 calc R . .
C31 C 0.3903(4) 0.5289(2) 0.31903(9) 0.0211(4) Uani 1 1 d . . .
O31 O 0.1929(3) 0.68341(18) 0.32381(7) 0.0294(3) Uani 1 1 d . . .
H31 H 0.093(5) 0.698(3) 0.2863(13) 0.035 Uiso 1 1 d . . .
O32 O 0.4140(3) 0.41949(18) 0.27322(7) 0.0298(4) Uani 1 1 d . . .
C32 C 0.5810(4) 0.5030(3) 0.37795(10) 0.0227(4) Uani 1 1 d . . .
H32A H 0.4795 0.5040 0.4265 0.027 Uiso 1 1 calc R . .
H32B H 0.6533 0.6064 0.3738 0.027 Uiso 1 1 calc R . .
C33 C 0.8136(4) 0.3289(3) 0.37396(10) 0.0226(4) Uani 1 1 d . . .
H33A H 0.9279 0.3335 0.3279 0.027 Uiso 1 1 calc R . .
H33B H 0.7428 0.2260 0.3728 0.027 Uiso 1 1 calc R . .
C34 C 0.9841(4) 0.2973(3) 0.43901(9) 0.0230(4) Uani 1 1 d . . .
H34A H 1.0549 0.4002 0.4401 0.028 Uiso 1 1 calc R . .
H34B H 0.8695 0.2930 0.4850 0.028 Uiso 1 1 calc R . .
C35 C 1.2172(4) 0.1229(3) 0.43539(10) 0.0237(4) Uani 1 1 d . . .
H35A H 1.3341 0.1286 0.3900 0.028 Uiso 1 1 calc R . .
H35B H 1.1466 0.0204 0.4329 0.028 Uiso 1 1 calc R . .
C36 C 1.3843(4) 0.0881(2) 0.50118(10) 0.0227(4) Uani 1 1 d . . .
H36A H 1.4571 0.1897 0.5031 0.027 Uiso 1 1 calc R . .
H36B H 1.2664 0.0848 0.5466 0.027 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C12 1.380(2) . ?
N11 C15 1.387(2) . ?
N11 C27 1.476(2) . ?
C12 N13 1.339(2) . ?
C12 C12 1.470(4) 2_565 ?
N13 C14 1.387(3) . ?
C14 C15 1.368(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C26 1.347(2) . ?
N21 C22 1.357(2) . ?
C22 C23 1.395(3) . ?
C22 C27 1.514(2) . ?
C23 C24 1.390(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.392(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.389(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C31 O32 1.222(2) . ?
C31 O31 1.332(2) . ?
C31 C32 1.524(2) . ?
O31 H31 0.89(3) . ?
C32 C33 1.527(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.539(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.530(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.536(2) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C36 1.533(4) 2_856 ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?

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
_geom_angle_publ_flag
C12 N11 C15 106.42(15) . . ?
C12 N11 C27 129.93(16) . . ?
C15 N11 C27 123.64(15) . . ?
N13 C12 N11 111.31(16) . . ?
N13 C12 C12 125.34(19) . 2_565 ?
N11 C12 C12 123.3(2) . 2_565 ?
C12 N13 C14 105.37(15) . . ?
C15 C14 N13 110.29(17) . . ?
C15 C14 H14 124.9 . . ?
N13 C14 H14 124.9 . . ?
C14 C15 N11 106.59(17) . . ?
C14 C15 H15 126.7 . . ?
N11 C15 H15 126.7 . . ?
C26 N21 C22 117.66(16) . . ?
N21 C22 C23 122.35(17) . . ?
N21 C22 C27 114.32(15) . . ?
C23 C22 C27 123.34(16) . . ?
C24 C23 C22 118.86(18) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C25 119.36(18) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C26 C25 C24 118.18(18) . . ?
C26 C25 H25 120.9 . . ?
C24 C25 H25 120.9 . . ?
N21 C26 C25 123.59(18) . . ?
N21 C26 H26 118.2 . . ?
C25 C26 H26 118.2 . . ?
N11 C27 C22 113.55(15) . . ?
N11 C27 H27A 108.9 . . ?
C22 C27 H27A 108.9 . . ?
N11 C27 H27B 108.9 . . ?
C22 C27 H27B 108.9 . . ?
H27A C27 H27B 107.7 . . ?
O32 C31 O31 123.93(17) . . ?
O32 C31 C32 123.90(17) . . ?
O31 C31 C32 112.16(15) . . ?
C31 O31 H31 109.6(15) . . ?
C31 C32 C33 114.11(15) . . ?
C31 C32 H32A 108.7 . . ?
C33 C32 H32A 108.7 . . ?
C31 C32 H32B 108.7 . . ?
C33 C32 H32B 108.7 . . ?
H32A C32 H32B 107.6 . . ?
C32 C33 C34 112.60(15) . . ?
C32 C33 H33A 109.1 . . ?
C34 C33 H33A 109.1 . . ?
C32 C33 H33B 109.1 . . ?
C34 C33 H33B 109.1 . . ?
H33A C33 H33B 107.8 . . ?
C35 C34 C33 112.87(15) . . ?
C35 C34 H34A 109.0 . . ?
C33 C34 H34A 109.0 . . ?
C35 C34 H34B 109.0 . . ?
C33 C34 H34B 109.0 . . ?
H34A C34 H34B 107.8 . . ?
C34 C35 C36 113.16(15) . . ?
C34 C35 H35A 108.9 . . ?
C36 C35 H35A 108.9 . . ?
C34 C35 H35B 108.9 . . ?
C36 C35 H35B 108.9 . . ?
H35A C35 H35B 107.8 . . ?
C36 C36 C35 113.63(18) 2_856 . ?
C36 C36 H36A 108.8 2_856 . ?
C35 C36 H36A 108.8 . . ?
C36 C36 H36B 108.8 2_856 . ?
C35 C36 H36B 108.8 . . ?
H36A C36 H36B 107.7 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 C12 N13 -1.5(2) . . . . ?
C27 N11 C12 N13 178.58(16) . . . . ?
C15 N11 C12 C12 178.3(2) . . . 2_565 ?
C27 N11 C12 C12 -1.6(3) . . . 2_565 ?
N11 C12 N13 C14 1.1(2) . . . . ?
C12 C12 N13 C14 -178.6(2) 2_565 . . . ?
C12 N13 C14 C15 -0.3(2) . . . . ?
N13 C14 C15 N11 -0.6(2) . . . . ?
C12 N11 C15 C14 1.2(2) . . . . ?
C27 N11 C15 C14 -178.84(16) . . . . ?
C26 N21 C22 C23 -0.8(3) . . . . ?
C26 N21 C22 C27 179.55(16) . . . . ?
N21 C22 C23 C24 0.6(3) . . . . ?
C27 C22 C23 C24 -179.77(17) . . . . ?
C22 C23 C24 C25 0.0(3) . . . . ?
C23 C24 C25 C26 -0.4(3) . . . . ?
C22 N21 C26 C25 0.4(3) . . . . ?
C24 C25 C26 N21 0.2(3) . . . . ?
C12 N11 C27 C22 89.6(2) . . . . ?
C15 N11 C27 C22 -90.3(2) . . . . ?
N21 C22 C27 N11 172.81(15) . . . . ?
C23 C22 C27 N11 -6.8(3) . . . . ?
O32 C31 C32 C33 1.7(3) . . . . ?
O31 C31 C32 C33 -179.06(15) . . . . ?
C31 C32 C33 C34 -173.72(15) . . . . ?
C32 C33 C34 C35 179.92(15) . . . . ?
C33 C34 C35 C36 -178.53(15) . . . . ?
C34 C35 C36 C36 179.00(18) . . . 2_856 ?

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 0.89(3) 1.86(3) 2.727(2) 163(2) .

_diffrn_measured_fraction_theta_max 0.940
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.954
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 1016843'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_A3:Pim

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-2B-8-C 1,1'-di[(2-pyridyl)methyl]-2,2'-biimidazole, [HOOC-(CH2)5-COOH]2
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H16 N6) (C7 H12 O4)2
;
_chemical_formula_sum            'C32 H40 N6 O8'
_chemical_formula_weight         636.70

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.9161(10)
_cell_length_b                   8.0077(16)
_cell_length_c                   20.828(4)
_cell_angle_alpha                87.266(11)
_cell_angle_beta                 88.665(10)
_cell_angle_gamma                72.608(9)
_cell_volume                     781.5(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3857
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      23.38

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             338
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9635
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21382
_diffrn_reflns_av_R_equivalents  0.0949
_diffrn_reflns_av_sigmaI/netI    0.1045
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         0.98
_diffrn_reflns_theta_max         31.05
_reflns_number_total             4657
_reflns_number_gt                2306
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4657
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1768
_refine_ls_R_factor_gt           0.0996
_refine_ls_wR_factor_ref         0.2647
_refine_ls_wR_factor_gt          0.2355
_refine_ls_goodness_of_fit_ref   1.286
_refine_ls_restrained_S_all      1.286
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?

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

_diffrn_measured_fraction_theta_max 0.933
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.100
_database_code_depnum_ccdc_archive 'CCDC 1016844'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_A4:Mal

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-2B-33 1,1'-di[(phenyl)methyl]-2,2'-biimidazole, HOOC-CH2-COOH
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C20 H18 N4) (C3 H4 O4)
;
_chemical_formula_sum            'C23 H22 N4 O4'
_chemical_formula_weight         418.45

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.4449(17)
_cell_length_b                   8.9002(15)
_cell_length_c                   21.338(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.855(10)
_cell_angle_gamma                90.00
_cell_volume                     2165.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4297
_cell_measurement_theta_min      4.16
_cell_measurement_theta_max      66.60

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8430
_exptl_absorpt_correction_T_max  0.9039
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10824
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.16
_diffrn_reflns_theta_max         67.60
_reflns_number_total             3641
_reflns_number_gt                2941
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0950P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3641
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1494
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.81578(14) 0.45649(16) 0.65574(7) 0.0196(4) Uani 1 1 d . . .
C12 C 0.75077(16) 0.3272(2) 0.66140(8) 0.0196(4) Uani 1 1 d . . .
N13 N 0.65240(14) 0.35641(18) 0.68877(7) 0.0236(4) Uani 1 1 d . . .
C14 C 0.65421(17) 0.5095(2) 0.70097(9) 0.0259(4) Uani 1 1 d . . .
H14 H 0.5949 0.5630 0.7202 0.031 Uiso 1 1 calc R . .
C15 C 0.75403(17) 0.5722(2) 0.68122(9) 0.0249(4) Uani 1 1 d . . .
H15 H 0.7765 0.6748 0.6844 0.030 Uiso 1 1 calc R . .
C21 C 0.90781(16) 0.5738(2) 0.56539(9) 0.0219(4) Uani 1 1 d . . .
C22 C 0.99254(18) 0.6822(2) 0.55403(10) 0.0267(5) Uani 1 1 d . . .
H22 H 1.0593 0.6947 0.5832 0.032 Uiso 1 1 calc R . .
C23 C 0.9794(2) 0.7724(2) 0.49975(11) 0.0365(5) Uani 1 1 d . . .
H23 H 1.0370 0.8459 0.4925 0.044 Uiso 1 1 calc R . .
C24 C 0.8818(2) 0.7538(3) 0.45660(10) 0.0403(6) Uani 1 1 d . . .
H24 H 0.8719 0.8165 0.4205 0.048 Uiso 1 1 calc R . .
C25 C 0.7991(2) 0.6438(3) 0.46641(10) 0.0379(6) Uani 1 1 d . . .
H25 H 0.7340 0.6293 0.4363 0.045 Uiso 1 1 calc R . .
C26 C 0.81160(18) 0.5539(2) 0.52071(10) 0.0295(5) Uani 1 1 d . . .
H26 H 0.7546 0.4792 0.5273 0.035 Uiso 1 1 calc R . .
C27 C 0.92505(16) 0.4753(2) 0.62409(9) 0.0225(4) Uani 1 1 d . . .
H27A H 0.9537 0.3753 0.6121 0.027 Uiso 1 1 calc R . .
H27B H 0.9858 0.5210 0.6540 0.027 Uiso 1 1 calc R . .
N31 N 0.71796(14) 0.06995(17) 0.61476(7) 0.0230(4) Uani 1 1 d . . .
C32 C 0.79049(16) 0.1776(2) 0.64331(8) 0.0192(4) Uani 1 1 d . . .
N33 N 0.89944(13) 0.12409(17) 0.65583(7) 0.0207(4) Uani 1 1 d . . .
C34 C 0.89680(18) -0.0225(2) 0.63365(9) 0.0262(4) Uani 1 1 d . . .
H34 H 0.9620 -0.0890 0.6358 0.031 Uiso 1 1 calc R . .
C35 C 0.78624(18) -0.0571(2) 0.60821(9) 0.0275(5) Uani 1 1 d . . .
H35 H 0.7611 -0.1500 0.5897 0.033 Uiso 1 1 calc R . .
C41 C 0.59451(16) 0.1600(2) 0.52017(9) 0.0231(4) Uani 1 1 d . . .
C42 C 0.51383(18) 0.2734(2) 0.50344(10) 0.0325(5) Uani 1 1 d . . .
H42 H 0.4629 0.3082 0.5332 0.039 Uiso 1 1 calc R . .
C43 C 0.5070(2) 0.3369(2) 0.44288(11) 0.0383(5) Uani 1 1 d . . .
H43 H 0.4509 0.4131 0.4318 0.046 Uiso 1 1 calc R . .
C44 C 0.5826(2) 0.2881(2) 0.39889(10) 0.0350(5) Uani 1 1 d . . .
H44 H 0.5792 0.3322 0.3582 0.042 Uiso 1 1 calc R . .
C45 C 0.66297(19) 0.1747(2) 0.41526(10) 0.0345(5) Uani 1 1 d . . .
H45 H 0.7140 0.1406 0.3854 0.041 Uiso 1 1 calc R . .
C46 C 0.66938(17) 0.1103(2) 0.47516(10) 0.0282(5) Uani 1 1 d . . .
H46 H 0.7245 0.0325 0.4857 0.034 Uiso 1 1 calc R . .
C47 C 0.59720(16) 0.0890(2) 0.58543(9) 0.0261(4) Uani 1 1 d . . .
H47A H 0.5525 0.1531 0.6128 0.031 Uiso 1 1 calc R . .
H47B H 0.5583 -0.0104 0.5820 0.031 Uiso 1 1 calc R . .
C51 C 0.38362(16) 0.2018(2) 0.71803(9) 0.0256(4) Uani 1 1 d . . .
O51 O 0.49189(12) 0.19490(16) 0.74579(7) 0.0292(4) Uani 1 1 d . . .
H51 H 0.547(2) 0.242(3) 0.7248(11) 0.035 Uiso 1 1 d . . .
O52 O 0.35803(14) 0.2610(2) 0.66729(8) 0.0509(5) Uani 1 1 d . . .
C52 C 0.29466(17) 0.1268(2) 0.75746(10) 0.0279(5) Uani 1 1 d . . .
H52A H 0.3268 0.0299 0.7739 0.033 Uiso 1 1 calc R . .
H52B H 0.2811 0.1917 0.7938 0.033 Uiso 1 1 calc R . .
C53 C 0.17900(16) 0.0991(2) 0.71893(9) 0.0232(4) Uani 1 1 d . . .
O53 O 0.10007(12) 0.20812(15) 0.72367(7) 0.0279(3) Uani 1 1 d . . .
H53 H 0.027(2) 0.178(2) 0.7010(11) 0.033 Uiso 1 1 d . . .
O54 O 0.16113(13) -0.01341(17) 0.68656(7) 0.0354(4) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C12 1.381(2) . ?
N11 C15 1.386(2) . ?
N11 C27 1.480(2) . ?
C12 N13 1.337(2) . ?
C12 C32 1.469(3) . ?
N13 C14 1.387(3) . ?
C14 C15 1.369(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C21 C22 1.403(3) . ?
C21 C26 1.405(3) . ?
C21 C27 1.528(3) . ?
C22 C23 1.407(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.396(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.405(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
N31 C32 1.375(2) . ?
N31 C35 1.388(3) . ?
N31 C47 1.478(2) . ?
C32 N33 1.340(2) . ?
N33 C34 1.388(2) . ?
C34 C35 1.369(3) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C41 C42 1.394(3) . ?
C41 C46 1.411(3) . ?
C41 C47 1.527(3) . ?
C42 C43 1.406(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.399(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.390(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.397(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C51 O52 1.217(2) . ?
C51 O51 1.329(2) . ?
C51 C52 1.528(3) . ?
O51 H51 0.91(3) . ?
C52 C53 1.518(3) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 O54 1.224(2) . ?
C53 O53 1.335(2) . ?
O53 H53 0.97(3) . ?

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
_geom_angle_publ_flag
C12 N11 C15 106.76(15) . . ?
C12 N11 C27 128.06(15) . . ?
C15 N11 C27 124.99(15) . . ?
N13 C12 N11 110.85(16) . . ?
N13 C12 C32 125.57(16) . . ?
N11 C12 C32 123.45(16) . . ?
C12 N13 C14 105.86(15) . . ?
C15 C14 N13 110.01(16) . . ?
C15 C14 H14 125.0 . . ?
N13 C14 H14 125.0 . . ?
C14 C15 N11 106.52(17) . . ?
C14 C15 H15 126.7 . . ?
N11 C15 H15 126.7 . . ?
C22 C21 C26 118.86(18) . . ?
C22 C21 C27 119.53(18) . . ?
C26 C21 C27 121.54(17) . . ?
C21 C22 C23 120.5(2) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 119.9(2) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 120.1(2) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.1(2) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 120.5(2) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
N11 C27 C21 112.55(15) . . ?
N11 C27 H27A 109.1 . . ?
C21 C27 H27A 109.1 . . ?
N11 C27 H27B 109.1 . . ?
C21 C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?
C32 N31 C35 106.74(16) . . ?
C32 N31 C47 127.99(16) . . ?
C35 N31 C47 124.39(16) . . ?
N33 C32 N31 110.95(16) . . ?
N33 C32 C12 124.94(16) . . ?
N31 C32 C12 123.98(17) . . ?
C32 N33 C34 105.83(16) . . ?
C35 C34 N33 109.84(17) . . ?
C35 C34 H34 125.1 . . ?
N33 C34 H34 125.1 . . ?
C34 C35 N31 106.63(16) . . ?
C34 C35 H35 126.7 . . ?
N31 C35 H35 126.7 . . ?
C42 C41 C46 118.69(19) . . ?
C42 C41 C47 119.68(18) . . ?
C46 C41 C47 121.60(18) . . ?
C41 C42 C43 120.69(19) . . ?
C41 C42 H42 119.7 . . ?
C43 C42 H42 119.7 . . ?
C44 C43 C42 120.2(2) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C45 C44 C43 119.4(2) . . ?
C45 C44 H44 120.3 . . ?
C43 C44 H44 120.3 . . ?
C44 C45 C46 120.7(2) . . ?
C44 C45 H45 119.7 . . ?
C46 C45 H45 119.7 . . ?
C45 C46 C41 120.39(19) . . ?
C45 C46 H46 119.8 . . ?
C41 C46 H46 119.8 . . ?
N31 C47 C41 112.30(15) . . ?
N31 C47 H47A 109.1 . . ?
C41 C47 H47A 109.1 . . ?
N31 C47 H47B 109.1 . . ?
C41 C47 H47B 109.1 . . ?
H47A C47 H47B 107.9 . . ?
O52 C51 O51 124.17(18) . . ?
O52 C51 C52 123.88(18) . . ?
O51 C51 C52 111.95(17) . . ?
C51 O51 H51 115.1(15) . . ?
C53 C52 C51 111.32(16) . . ?
C53 C52 H52A 109.4 . . ?
C51 C52 H52A 109.4 . . ?
C53 C52 H52B 109.4 . . ?
C51 C52 H52B 109.4 . . ?
H52A C52 H52B 108.0 . . ?
O54 C53 O53 123.74(18) . . ?
O54 C53 C52 122.32(17) . . ?
O53 C53 C52 113.94(17) . . ?
C53 O53 H53 108.6(13) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 C12 N13 0.1(2) . . . . ?
C27 N11 C12 N13 -175.00(16) . . . . ?
C15 N11 C12 C32 -176.03(17) . . . . ?
C27 N11 C12 C32 8.8(3) . . . . ?
N11 C12 N13 C14 0.1(2) . . . . ?
C32 C12 N13 C14 176.17(18) . . . . ?
C12 N13 C14 C15 -0.3(2) . . . . ?
N13 C14 C15 N11 0.4(2) . . . . ?
C12 N11 C15 C14 -0.3(2) . . . . ?
C27 N11 C15 C14 175.00(17) . . . . ?
C26 C21 C22 C23 1.9(3) . . . . ?
C27 C21 C22 C23 178.94(17) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
C22 C23 C24 C25 -1.6(3) . . . . ?
C23 C24 C25 C26 1.9(3) . . . . ?
C22 C21 C26 C25 -1.6(3) . . . . ?
C27 C21 C26 C25 -178.58(17) . . . . ?
C24 C25 C26 C21 -0.3(3) . . . . ?
C12 N11 C27 C21 112.7(2) . . . . ?
C15 N11 C27 C21 -61.6(2) . . . . ?
C22 C21 C27 N11 137.30(17) . . . . ?
C26 C21 C27 N11 -45.8(2) . . . . ?
C35 N31 C32 N33 -1.0(2) . . . . ?
C47 N31 C32 N33 -170.52(16) . . . . ?
C35 N31 C32 C12 -177.05(17) . . . . ?
C47 N31 C32 C12 13.4(3) . . . . ?
N13 C12 C32 N33 -132.7(2) . . . . ?
N11 C12 C32 N33 42.9(3) . . . . ?
N13 C12 C32 N31 42.7(3) . . . . ?
N11 C12 C32 N31 -141.67(19) . . . . ?
N31 C32 N33 C34 0.8(2) . . . . ?
C12 C32 N33 C34 176.83(17) . . . . ?
C32 N33 C34 C35 -0.4(2) . . . . ?
N33 C34 C35 N31 -0.3(2) . . . . ?
C32 N31 C35 C34 0.7(2) . . . . ?
C47 N31 C35 C34 170.73(17) . . . . ?
C46 C41 C42 C43 0.1(3) . . . . ?
C47 C41 C42 C43 -177.80(18) . . . . ?
C41 C42 C43 C44 -0.9(3) . . . . ?
C42 C43 C44 C45 1.2(3) . . . . ?
C43 C44 C45 C46 -0.6(3) . . . . ?
C44 C45 C46 C41 -0.2(3) . . . . ?
C42 C41 C46 C45 0.5(3) . . . . ?
C47 C41 C46 C45 178.34(18) . . . . ?
C32 N31 C47 C41 77.9(2) . . . . ?
C35 N31 C47 C41 -89.9(2) . . . . ?
C42 C41 C47 N31 -136.09(19) . . . . ?
C46 C41 C47 N31 46.1(2) . . . . ?
O52 C51 C52 C53 14.9(3) . . . . ?
O51 C51 C52 C53 -165.22(16) . . . . ?
C51 C52 C53 O54 85.6(2) . . . . ?
C51 C52 C53 O53 -94.2(2) . . . . ?

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
O51 H51 N13 0.91(3) 1.80(3) 2.702(2) 172(2) .
O53 H53 N33 0.97(3) 1.75(3) 2.714(2) 177(2) 1_455

_diffrn_measured_fraction_theta_max 0.930
_diffrn_reflns_theta_full        66.00
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.085

#END


_database_code_depnum_ccdc_archive 'CCDC 1016845'
