#------------------------------------------------------------------------------
#$Date: 2017-07-21 05:23:14 +0300 (Fri, 21 Jul 2017) $
#$Revision: 198878 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/65/1546570.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_1546570
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(C6 F4 I2)'
_chemical_formula_sum            'C15 H11 F2 I N5'
_chemical_formula_weight         426.19
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2017-02-17 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                93.952(13)
_cell_angle_beta                 93.442(12)
_cell_angle_gamma                105.938(16)
_cell_formula_units_Z            2
_cell_length_a                   5.0691(14)
_cell_length_b                   8.055(2)
_cell_length_c                   19.750(5)
_cell_measurement_reflns_used    8749
_cell_measurement_temperature    130.(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.64
_cell_volume                     771.0(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      130.(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16067
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.04
_exptl_absorpt_coefficient_mu    2.104
_exptl_absorpt_correction_T_max  0.80
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plates
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.512
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.218
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0236
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0407P)²+0.0281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0768
_reflns_number_gt                2891
_reflns_number_total             3140
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7fd00080d2.cif
_cod_data_source_block           A1XBD2
_cod_database_code               1546570
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.8965(7) 0.9307(4) 0.12428(15) 0.0198(7) Uani d . . 1
N N2 0.9365(6) 0.9396(4) 0.19353(13) 0.0177(6) Uani d . . 1
C C3 1.1895(7) 1.0532(5) 0.21162(17) 0.0225(7) Uani d . . 1
H H3 1.2764 1.085 0.2564 0.027 Uiso calc U R 1
C C4 1.2927(8) 1.1118(5) 0.15304(17) 0.0272(8) Uani d . . 1
H H4 1.4656 1.1943 0.1503 0.033 Uiso calc U R 1
N N5 1.1102(6) 1.0341(4) 0.09839(14) 0.0251(7) Uani d . . 1
C C6 0.6560(8) 0.8200(5) 0.08497(16) 0.0261(8) Uani d . . 1
N N7 0.4498(7) 0.7080(5) 0.10874(16) 0.0447(10) Uani d . . 1
C C8 0.2726(11) 0.6379(8) 0.0532(2) 0.074(2) Uani d . . 1
H H8 0.1011 0.5529 0.0542 0.088 Uiso calc U R 1
C C9 0.3754(10) 0.7065(8) -0.0040(2) 0.070(2) Uani d . . 1
H H9 0.2924 0.6786 -0.0493 0.084 Uiso calc U R 1
H H10 0.731(9) 0.881(6) -0.007(2) 0.035(11) Uiso d . . 1
N N10 0.6202(7) 0.8226(5) 0.01696(15) 0.0349(8) Uani d . . 1
C C11 0.7491(7) 0.8515(4) 0.24136(15) 0.0194(7) Uani d . . 1
H H11A 0.5574 0.8359 0.2227 0.023 Uiso calc U R 1
H H11B 0.7793 0.926 0.2847 0.023 Uiso calc U R 1
C C12 0.7839(7) 0.6766(4) 0.25590(15) 0.0171(7) Uani d . . 1
N N13 0.6460(6) 0.6101(4) 0.30806(13) 0.0197(6) Uani d . . 1
C C14 0.6666(8) 0.4565(5) 0.32492(18) 0.0276(8) Uani d . . 1
H H14 0.5692 0.4076 0.3617 0.033 Uiso calc U R 1
C C15 0.8222(8) 0.3640(5) 0.29176(19) 0.0302(8) Uani d . . 1
H H15 0.8314 0.2549 0.3055 0.036 Uiso calc U R 1
C C16 0.9635(8) 0.4350(5) 0.23814(19) 0.0305(9) Uani d . . 1
H H16 1.0725 0.3754 0.2143 0.037 Uiso calc U R 1
C C17 0.9441(7) 0.5938(5) 0.21963(16) 0.0217(7) Uani d . . 1
H H17 1.0385 0.6451 0.1828 0.026 Uiso calc U R 1
C C18 0.1462(7) 0.9131(4) 0.45820(15) 0.0185(7) Uani d . . 1
C C19 0.0990(7) 1.0653(5) 0.44266(15) 0.0206(7) Uani d . . 1
C C20 0.0440(7) 0.8471(5) 0.51703(16) 0.0218(7) Uani d . . 1
I I21 0.35814(4) 0.78259(3) 0.39475(2) 0.01967(10) Uani d . . 1
F F22 0.1911(5) 1.1361(3) 0.38509(10) 0.0329(5) Uani d . . 1
F F23 0.0832(5) 0.6999(3) 0.53605(10) 0.0363(6) Uani d . . 1
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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_site_symmetry_3
_geom_angle
N5 C1 N2 . 110.9(3)
N5 C1 C6 . 125.0(3)
N2 C1 C6 . 124.1(3)
C1 N2 C3 . 106.9(3)
C1 N2 C11 . 128.4(3)
C3 N2 C11 . 124.8(3)
C4 C3 N2 . 106.6(3)
C4 C3 H3 . 126.7
N2 C3 H3 . 126.7
C3 C4 N5 . 109.9(3)
C3 C4 H4 . 125.1
N5 C4 H4 . 125.1
C1 N5 C4 . 105.7(3)
N7 C6 N10 . 112.0(3)
N7 C6 C1 . 126.3(3)
N10 C6 C1 . 121.7(3)
C6 N7 C8 . 104.8(3)
N7 C8 C9 . 110.5(4)
N7 C8 H8 . 124.7
C9 C8 H8 . 124.7
N10 C9 C8 . 105.8(4)
N10 C9 H9 . 127.1
C8 C9 H9 . 127.1
C6 N10 C9 . 107.0(3)
C6 N10 H10 . 126.(3)
C9 N10 H10 . 127.(3)
N2 C11 C12 . 113.6(3)
N2 C11 H11A . 108.8
C12 C11 H11A . 108.8
N2 C11 H11B . 108.8
C12 C11 H11B . 108.8
H11A C11 H11B . 107.7
N13 C12 C17 . 123.2(3)
N13 C12 C11 . 113.1(3)
C17 C12 C11 . 123.6(3)
C14 N13 C12 . 117.3(3)
C14 N13 I21 . 116.7(2)
C12 N13 I21 . 125.6(2)
N13 C14 C15 . 123.7(3)
N13 C14 H14 . 118.2
C15 C14 H14 . 118.2
C16 C15 C14 . 118.2(3)
C16 C15 H15 . 120.9
C14 C15 H15 . 120.9
C17 C16 C15 . 119.1(3)
C17 C16 H16 . 120.5
C15 C16 H16 . 120.5
C16 C17 C12 . 118.5(3)
C16 C17 H17 . 120.7
C12 C17 H17 . 120.7
C19 C18 C20 . 116.7(3)
C19 C18 I21 . 121.7(2)
C20 C18 I21 . 121.6(3)
F22 C19 C18 . 119.7(3)
F22 C19 C20 2_576 117.3(3)
C18 C19 C20 2_576 122.9(3)
F23 C20 C18 . 120.4(3)
F23 C20 C19 2_576 119.2(3)
C18 C20 C19 2_576 120.3(3)
C18 I21 N13 . 179.26(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N5 . 1.326(4)
C1 N2 . 1.365(4)
C1 C6 . 1.442(5)
N2 C3 . 1.366(5)
N2 C11 . 1.459(4)
C3 C4 . 1.359(4)
C3 H3 . 0.95
C4 N5 . 1.372(5)
C4 H4 . 0.95
C6 N7 . 1.314(5)
C6 N10 . 1.347(4)
N7 C8 . 1.358(6)
C8 C9 . 1.362(6)
C8 H8 . 0.95
C9 N10 . 1.354(5)
C9 H9 . 0.95
N10 H10 . 0.83(4)
C11 C12 . 1.511(5)
C11 H11A . 0.99
C11 H11B . 0.99
C12 N13 . 1.339(4)
C12 C17 . 1.385(4)
N13 C14 . 1.332(5)
N13 I21 . 2.842(3)
C14 C15 . 1.387(5)
C14 H14 . 0.95
C15 C16 . 1.382(5)
C15 H15 . 0.95
C16 C17 . 1.382(5)
C16 H16 . 0.95
C17 H17 . 0.95
C18 C19 . 1.363(5)
C18 C20 . 1.381(4)
C18 I21 . 2.105(3)
C19 F22 . 1.357(3)
C19 C20 2_576 1.389(5)
C20 F23 . 1.330(4)
C20 C19 2_576 1.389(5)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N10 H10 N5 2_775 0.83(4) 2.10(4) 2.874(4) 156.(4)
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_site_symmetry_4
_geom_torsion
N5 C1 N2 C3 . -0.6(4)
C6 C1 N2 C3 . 178.0(3)
N5 C1 N2 C11 . 177.8(3)
C6 C1 N2 C11 . -3.6(5)
C1 N2 C3 C4 . 1.0(4)
C11 N2 C3 C4 . -177.5(3)
N2 C3 C4 N5 . -1.1(4)
N2 C1 N5 C4 . -0.1(4)
C6 C1 N5 C4 . -178.7(4)
C3 C4 N5 C1 . 0.8(4)
N5 C1 C6 N7 . 175.2(4)
N2 C1 C6 N7 . -3.2(6)
N5 C1 C6 N10 . -5.0(6)
N2 C1 C6 N10 . 176.6(4)
N10 C6 N7 C8 . -0.9(6)
C1 C6 N7 C8 . 178.9(5)
C6 N7 C8 C9 . 0.9(7)
N7 C8 C9 N10 . -0.6(8)
N7 C6 N10 C9 . 0.6(6)
C1 C6 N10 C9 . -179.2(4)
C8 C9 N10 C6 . 0.0(7)
C1 N2 C11 C12 . 90.1(4)
C3 N2 C11 C12 . -91.7(4)
N2 C11 C12 N13 . 169.3(3)
N2 C11 C12 C17 . -10.1(5)
C17 C12 N13 C14 . -0.1(5)
C11 C12 N13 C14 . -179.5(3)
C17 C12 N13 I21 . 173.2(3)
C11 C12 N13 I21 . -6.2(4)
C12 N13 C14 C15 . 0.2(5)
I21 N13 C14 C15 . -173.6(3)
N13 C14 C15 C16 . -0.1(6)
C14 C15 C16 C17 . -0.2(6)
C15 C16 C17 C12 . 0.3(6)
N13 C12 C17 C16 . -0.2(5)
C11 C12 C17 C16 . 179.1(3)
C20 C18 C19 F22 . -179.2(3)
I21 C18 C19 F22 . -0.3(5)
C20 C18 C19 C20 2_576 0.1(6)
I21 C18 C19 C20 2_576 179.0(3)
C19 C18 C20 F23 . -179.5(3)
I21 C18 C20 F23 . 1.6(5)
C19 C18 C20 C19 2_576 -0.1(6)
I21 C18 C20 C19 2_576 -179.0(3)
