#------------------------------------------------------------------------------
#$Date: 2017-07-21 05:23:14 +0300 (Fri, 21 Jul 2017) $
#$Revision: 198878 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/65/1546575.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1546575
loop_
_publ_author_name
'Gunawardana, C. A.'
'Desper, J.'
'Sinha, A. S.'
'Ðaković, M.'
'Aakeröy, C. B.'
_publ_section_title
;
 Competition and selectivity in supramolecular synthesis: structural
 landscape around 1-(pyridylmethyl)-2,2′-biimidazoles
;
_journal_name_full               'Faraday Discuss.'
_journal_paper_doi               10.1039/C7FD00080D
_journal_year                    2017
_chemical_formula_moiety         'C12 H11 N5, 0.5(C12 H22 O4)'
_chemical_formula_sum            'C18 H22 N5 O2'
_chemical_formula_weight         340.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                81.583(5)
_cell_angle_beta                 85.500(6)
_cell_angle_gamma                70.615(5)
_cell_formula_units_Z            2
_cell_length_a                   5.2936(3)
_cell_length_b                   7.9437(5)
_cell_length_c                   22.8847(13)
_cell_measurement_reflns_used    1919
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.4450
_cell_measurement_theta_min      4.4600
_cell_volume                     897.53(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
;
_computing_molecular_graphics
;
Mercury (Bruno et al., 2002)
;
_computing_publication_material
;
SHELXL-2013 (Sheldrick, 2013) and PLATON (Spek, 2003)
;
_computing_structure_refinement
;
SHELXL-2014/7 (Sheldrick, 2014)
;
_computing_structure_solution
;
SHELXS-2014/7 (Sheldrick, 2014)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7915
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         4.293
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0654
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0541P)²+0.2412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1569
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2254
_reflns_number_total             3140
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7fd00080d2.cif
_cod_data_source_block           A1HBD6
_cod_database_code               1546575
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.7326(4) 1.0200(3) 0.18557(9) 0.0801(7) Uani 1 1 d . .
O2 O 0.7980(4) 0.7706(3) 0.14596(10) 0.0787(7) Uani 1 1 d . .
N1 N 0.1287(4) 0.9729(3) 0.32967(9) 0.0515(6) Uani 1 1 d . .
N2 N -0.0718(4) 1.0558(3) 0.41466(10) 0.0643(7) Uani 1 1 d . .
N3 N 0.5868(5) 0.7159(4) 0.39931(13) 0.0986(10) Uani 1 1 d . .
N4 N 0.3870(5) 0.8229(4) 0.48096(12) 0.0852(9) Uani 1 1 d . .
N5 N 0.4629(4) 0.6512(3) 0.22548(10) 0.0579(6) Uani 1 1 d . .
C1 C 0.1479(5) 0.9525(3) 0.38963(12) 0.0512(6) Uani 1 1 d . .
C2 C 0.3741(5) 0.8314(4) 0.42199(13) 0.0630(7) Uani 1 1 d . .
C3 C 0.6224(8) 0.6978(7) 0.49719(18) 0.145(2) Uani 1 1 d . .
H3 H 0.6887 0.6623 0.5351 0.174 Uiso 1 1 calc R U
C4 C 0.7410(8) 0.6351(7) 0.44682(19) 0.154(2) Uani 1 1 d . .
H4 H 0.9082 0.5473 0.4448 0.185 Uiso 1 1 calc R U
C5 C -0.1183(6) 1.0939(4) 0.31670(13) 0.0637(8) Uani 1 1 d . .
H5 H -0.1904 1.1337 0.2794 0.076 Uiso 1 1 calc R U
C6 C -0.2367(6) 1.1443(4) 0.36825(13) 0.0726(9) Uani 1 1 d . .
H6 H -0.4067 1.2276 0.3722 0.087 Uiso 1 1 calc R U
C7 C 0.3268(5) 0.8894(3) 0.28560(12) 0.0572(7) Uani 1 1 d . .
H7A H 0.5045 0.8655 0.3000 0.069 Uiso 1 1 calc R U
H7B H 0.3078 0.9737 0.2497 0.069 Uiso 1 1 calc R U
C8 C 0.3043(5) 0.7169(3) 0.27089(11) 0.0480(6) Uani 1 1 d . .
C9 C 0.1352(5) 0.6329(3) 0.30060(13) 0.0616(7) Uani 1 1 d . .
H9 H 0.0248 0.6821 0.3317 0.074 Uiso 1 1 calc R U
C10 C 0.1313(7) 0.4736(4) 0.28364(16) 0.0785(9) Uani 1 1 d . .
H10 H 0.0183 0.4139 0.3030 0.094 Uiso 1 1 calc R U
C11 C 0.2978(7) 0.4054(4) 0.23761(16) 0.0825(10) Uani 1 1 d . .
H11 H 0.3011 0.2980 0.2254 0.099 Uiso 1 1 calc R U
C12 C 0.4570(6) 0.4980(4) 0.21034(15) 0.0739(9) Uani 1 1 d . .
H12 H 0.5689 0.4511 0.1791 0.089 Uiso 1 1 calc R U
C13 C 0.8399(5) 0.9241(4) 0.14895(12) 0.0551(7) Uani 1 1 d . .
C14 C 1.0286(5) 0.9656(4) 0.10137(13) 0.0629(8) Uani 1 1 d . .
H14A H 0.9553 0.9707 0.0634 0.075 Uiso 1 1 calc R U
H14B H 1.1971 0.8675 0.1041 0.075 Uiso 1 1 calc R U
C15 C 1.0843(5) 1.1392(4) 0.10317(12) 0.0593(7) Uani 1 1 d . .
H15A H 1.1761 1.1292 0.1392 0.071 Uiso 1 1 calc R U
H15B H 0.9149 1.2358 0.1047 0.071 Uiso 1 1 calc R U
C16 C 1.2516(5) 1.1890(4) 0.05114(12) 0.0594(7) Uani 1 1 d . .
H16A H 1.4202 1.0916 0.0495 0.071 Uiso 1 1 calc R U
H16B H 1.1590 1.1995 0.0152 0.071 Uiso 1 1 calc R U
C17 C 1.3106(5) 1.3610(4) 0.05252(12) 0.0599(7) Uani 1 1 d . .
H17A H 1.4079 1.3491 0.0879 0.072 Uiso 1 1 calc R U
H17B H 1.1421 1.4577 0.0554 0.072 Uiso 1 1 calc R U
C18 C 1.4714(5) 1.4135(4) -0.00046(12) 0.0627(7) Uani 1 1 d . .
H18A H 1.6406 1.3173 -0.0031 0.075 Uiso 1 1 calc R U
H18B H 1.3750 1.4241 -0.0359 0.075 Uiso 1 1 calc R U
H1O H 0.682(7) 0.731(5) 0.1772(18) 0.116(13) Uiso 1 1 d . .
H1N H 0.268(7) 0.880(4) 0.5048(15) 0.089(11) Uiso 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C13 O2 H1O 118(2) .
C5 N1 C1 106.7(2) .
C5 N1 C7 124.3(2) .
C1 N1 C7 129.0(2) .
C1 N2 C6 104.7(2) .
C2 N3 C4 103.6(3) .
C2 N4 C3 107.2(3) .
C2 N4 H1N 128(2) .
C3 N4 H1N 125(2) .
C12 N5 C8 117.8(2) .
N2 C1 N1 111.3(2) .
N2 C1 C2 124.0(2) .
N1 C1 C2 124.7(2) .
N3 C2 N4 112.1(3) .
N3 C2 C1 125.9(3) .
N4 C2 C1 122.1(2) .
C4 C3 N4 105.4(4) .
C4 C3 H3 127.3 .
N4 C3 H3 127.3 .
C3 C4 N3 111.8(3) .
C3 C4 H4 124.1 .
N3 C4 H4 124.1 .
C6 C5 N1 106.6(2) .
C6 C5 H5 126.7 .
N1 C5 H5 126.7 .
C5 C6 N2 110.7(2) .
C5 C6 H6 124.6 .
N2 C6 H6 124.6 .
N1 C7 C8 114.0(2) .
N1 C7 H7A 108.8 .
C8 C7 H7A 108.8 .
N1 C7 H7B 108.8 .
C8 C7 H7B 108.8 .
H7A C7 H7B 107.7 .
N5 C8 C9 122.1(2) .
N5 C8 C7 114.2(2) .
C9 C8 C7 123.6(2) .
C8 C9 C10 118.9(3) .
C8 C9 H9 120.5 .
C10 C9 H9 120.5 .
C11 C10 C9 118.6(3) .
C11 C10 H10 120.7 .
C9 C10 H10 120.7 .
C12 C11 C10 118.6(3) .
C12 C11 H11 120.7 .
C10 C11 H11 120.7 .
N5 C12 C11 123.9(3) .
N5 C12 H12 118.0 .
C11 C12 H12 118.0 .
O1 C13 O2 122.8(3) .
O1 C13 C14 124.2(3) .
O2 C13 C14 113.0(2) .
C13 C14 C15 115.0(2) .
C13 C14 H14A 108.5 .
C15 C14 H14A 108.5 .
C13 C14 H14B 108.5 .
C15 C14 H14B 108.5 .
H14A C14 H14B 107.5 .
C14 C15 C16 114.3(2) .
C14 C15 H15A 108.7 .
C16 C15 H15A 108.7 .
C14 C15 H15B 108.7 .
C16 C15 H15B 108.7 .
H15A C15 H15B 107.6 .
C17 C16 C15 114.9(2) .
C17 C16 H16A 108.5 .
C15 C16 H16A 108.5 .
C17 C16 H16B 108.5 .
C15 C16 H16B 108.5 .
H16A C16 H16B 107.5 .
C16 C17 C18 114.9(2) .
C16 C17 H17A 108.5 .
C18 C17 H17A 108.5 .
C16 C17 H17B 108.5 .
C18 C17 H17B 108.5 .
H17A C17 H17B 107.5 .
C18 C18 C17 115.1(3) 2_885
C18 C18 H18A 108.5 2_885
C17 C18 H18A 108.5 .
C18 C18 H18B 108.5 2_885
C17 C18 H18B 108.5 .
H18A C18 H18B 107.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C13 1.196(3) .
O2 C13 1.322(3) .
O2 H1O 0.99(4) .
N1 C5 1.366(3) .
N1 C1 1.366(3) .
N1 C7 1.458(3) .
N2 C1 1.324(3) .
N2 C6 1.380(3) .
N3 C2 1.319(3) .
N3 C4 1.359(5) .
N4 C2 1.347(4) .
N4 C3 1.349(4) .
N4 H1N 0.86(3) .
N5 C12 1.324(3) .
N5 C8 1.337(3) .
C1 C2 1.440(4) .
C3 C4 1.348(5) .
C3 H3 0.9300 .
C4 H4 0.9300 .
C5 C6 1.342(4) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C8 1.502(3) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.370(4) .
C9 C10 1.383(4) .
C9 H9 0.9300 .
C10 C11 1.373(4) .
C10 H10 0.9300 .
C11 C12 1.355(4) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 C14 1.495(4) .
C14 C15 1.509(4) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C16 1.512(4) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.505(4) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18 1.515(4) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 C18 1.505(5) 2_885
C18 H18A 0.9700 .
C18 H18B 0.9700 .
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
C5 H5 O1 0.93 2.56 3.342(4) 142.2 1_455
C7 H7A N3 0.97 2.41 2.970(4) 116.6 .
C9 H9 N3 0.93 2.64 3.479(4) 149.8 1_455
O2 H1O N5 0.99(4) 1.75(4) 2.732(3) 173(3) .
N4 H1N N2 0.86(3) 2.09(3) 2.898(4) 158(3) 2_576
C5 H5 O1 0.93 2.56 3.342(4) 142.2 1_455
C7 H7A N3 0.97 2.41 2.970(4) 116.6 .
C9 H9 N3 0.93 2.64 3.479(4) 149.8 1_455
O2 H1O N5 0.99(4) 1.75(4) 2.732(3) 173(3) .
N4 H1N N2 0.86(3) 2.09(3) 2.898(4) 158(3) 2_576
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_4
C6 N2 C1 N1 0.3(3) .
C6 N2 C1 C2 -178.2(3) .
C5 N1 C1 N2 -0.8(3) .
C7 N1 C1 N2 177.9(2) .
C5 N1 C1 C2 177.7(2) .
C7 N1 C1 C2 -3.6(4) .
C4 N3 C2 N4 -1.4(4) .
C4 N3 C2 C1 179.6(4) .
C3 N4 C2 N3 1.1(5) .
C3 N4 C2 C1 -179.8(3) .
N2 C1 C2 N3 174.1(3) .
N1 C1 C2 N3 -4.2(5) .
N2 C1 C2 N4 -4.8(4) .
N1 C1 C2 N4 176.9(3) .
C2 N4 C3 C4 -0.3(6) .
N4 C3 C4 N3 -0.5(7) .
C2 N3 C4 C3 1.1(6) .
C1 N1 C5 C6 1.0(3) .
C7 N1 C5 C6 -177.8(2) .
N1 C5 C6 N2 -0.9(3) .
C1 N2 C6 C5 0.4(3) .
C5 N1 C7 C8 -89.5(3) .
C1 N1 C7 C8 92.0(3) .
C12 N5 C8 C9 -1.4(4) .
C12 N5 C8 C7 179.1(2) .
N1 C7 C8 N5 172.2(2) .
N1 C7 C8 C9 -7.3(4) .
N5 C8 C9 C10 1.0(4) .
C7 C8 C9 C10 -179.6(3) .
C8 C9 C10 C11 0.1(5) .
C9 C10 C11 C12 -0.6(5) .
C8 N5 C12 C11 0.9(5) .
C10 C11 C12 N5 0.2(5) .
O1 C13 C14 C15 1.7(4) .
O2 C13 C14 C15 -179.6(2) .
C13 C14 C15 C16 -173.8(2) .
C14 C15 C16 C17 -179.6(2) .
C15 C16 C17 C18 -178.3(2) .
C16 C17 C18 C18 179.4(3) 2_885
