#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:26:07 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180505 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/74/7217401.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_7217401
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Wijethunga, Tharanga K.'
'Haj, Mohammad Abul'
'Desper, John'
'Moore, Curtis'
_publ_section_title
;
 The structural landscape of heteroaryl-2-imidazoles: competing halogen-
 and hydrogen-bond interactions
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              7218
_journal_paper_doi               10.1039/C4CE00803K
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety
;
(C8 H7 N3)2 (C6 F4 I2)
;
_chemical_formula_sum            'C22 H14 F4 I2 N6'
_chemical_formula_weight         692.19
_chemical_name_systematic
;
TW-1-107 [2-(4-pyridyl)-imidazole]2, 1,4-diiodotetrafluorobenzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.470(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.9720(11)
_cell_length_b                   5.0426(4)
_cell_length_c                   17.0878(15)
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.70
_cell_measurement_theta_min      3.14
_cell_volume                     1116.72(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.975
_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  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17748
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         32.56
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    2.874
_exptl_absorpt_correction_T_max  0.8465
_exptl_absorpt_correction_T_min  0.3782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.059
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.046
_refine_diff_density_min         -0.910
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0256
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0622
_reflns_number_gt                3386
_reflns_number_total             3962
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7216657
_cod_data_source_file            c4ce00803k2.cif
_cod_data_source_block           A1D8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7217401
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'
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
N11A N 0.36473(14) 0.8137(3) 0.59714(10) 0.0183(3) Uani 0.20(4) 1 d P A 1
H11 H 0.3747 0.9746 0.5791 0.022 Uiso 0.20(4) 1 calc PR A 1
N11B N 0.36473(14) 0.8137(3) 0.59714(10) 0.0183(3) Uani 0.80(4) 1 d P A 2
C12 C 0.35176(15) 0.5917(4) 0.55588(11) 0.0156(3) Uani 1 1 d . . .
N13A N 0.33756(14) 0.3804(3) 0.60345(10) 0.0180(3) Uani 0.20(4) 1 d P A 1
N13B N 0.33756(14) 0.3804(3) 0.60345(10) 0.0180(3) Uani 0.80(4) 1 d P A 2
H13 H 0.3268 0.2153 0.5885 0.022 Uiso 0.80(4) 1 calc PR A 2
C14 C 0.34314(17) 0.4721(4) 0.67897(12) 0.0210(4) Uani 1 1 d . . .
H14 H 0.3371 0.3705 0.7254 0.025 Uiso 1 1 calc R A 1
C15 C 0.35915(16) 0.7378(4) 0.67402(12) 0.0201(4) Uani 1 1 d . A .
H15 H 0.3656 0.8546 0.7176 0.024 Uiso 1 1 calc R B 1
N21 N 0.35680(14) 0.5442(4) 0.30754(10) 0.0207(3) Uani 1 1 d . . .
C22 C 0.30450(17) 0.3680(4) 0.34869(12) 0.0205(4) Uani 1 1 d . A .
H22 H 0.2684 0.2309 0.3209 0.025 Uiso 1 1 calc R . .
C23 C 0.29987(16) 0.3735(4) 0.42938(12) 0.0186(4) Uani 1 1 d . . .
H23 H 0.2619 0.2431 0.4561 0.022 Uiso 1 1 calc R A .
C24 C 0.35218(15) 0.5747(4) 0.47089(11) 0.0158(3) Uani 1 1 d . A .
C25 C 0.40579(16) 0.7602(4) 0.42803(12) 0.0185(4) Uani 1 1 d . . .
H25 H 0.4418 0.9013 0.4539 0.022 Uiso 1 1 calc R A .
C26 C 0.40610(17) 0.7372(4) 0.34754(12) 0.0205(4) Uani 1 1 d . A .
H26 H 0.4432 0.8650 0.3192 0.025 Uiso 1 1 calc R . .
C31 C 0.47059(15) 0.1446(4) 0.06597(12) 0.0176(4) Uani 1 1 d . . .
I1 I 0.421719(10) 0.34197(3) 0.165311(7) 0.01899(5) Uani 1 1 d . . .
C32 C 0.54516(15) -0.0516(4) 0.07214(11) 0.0181(4) Uani 1 1 d . . .
F32 F 0.59176(10) -0.1067(3) 0.14199(7) 0.0239(3) Uani 1 1 d . . .
C36 C 0.42647(15) 0.1935(4) -0.00762(12) 0.0180(4) Uani 1 1 d . . .
F36 F 0.35527(10) 0.3855(3) -0.01777(8) 0.0243(3) Uani 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C12 N11A C15 105.20(17) . .
C12 N11A H11 127.4 . .
C15 N11A H11 127.4 . .
N11A C12 N13A 111.14(17) . .
N11A C12 C24 124.97(18) . .
N13A C12 C24 123.89(18) . .
C12 N13A C14 107.22(17) . .
C15 C14 N13A 106.03(18) . .
C15 C14 H14 127.0 . .
N13A C14 H14 127.0 . .
C14 C15 N11A 110.40(18) . .
C14 C15 H15 124.8 . .
N11A C15 H15 124.8 . .
C22 N21 C26 117.25(18) . .
C22 N21 I1 113.16(13) . .
C26 N21 I1 123.66(14) . .
N21 C22 C23 123.78(19) . .
N21 C22 H22 118.1 . .
C23 C22 H22 118.1 . .
C22 C23 C24 118.68(19) . .
C22 C23 H23 120.7 . .
C24 C23 H23 120.7 . .
C25 C24 C23 117.62(18) . .
C25 C24 C12 120.57(18) . .
C23 C24 C12 121.81(18) . .
C26 C25 C24 119.38(19) . .
C26 C25 H25 120.3 . .
C24 C25 H25 120.3 . .
N21 C26 C25 123.3(2) . .
N21 C26 H26 118.4 . .
C25 C26 H26 118.4 . .
C36 C31 C32 117.24(18) . .
C36 C31 I1 121.74(15) . .
C32 C31 I1 120.93(14) . .
C31 I1 N21 172.82(7) . .
F32 C32 C36 118.57(18) . 3_655
F32 C32 C31 120.10(18) . .
C36 C32 C31 121.33(18) 3_655 .
F36 C36 C32 118.46(18) . 3_655
F36 C36 C31 120.11(18) . .
C32 C36 C31 121.42(19) 3_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11A C12 1.330(3) .
N11A C15 1.373(3) .
N11A H11 0.8800 .
C12 N13A 1.358(3) .
C12 C24 1.455(3) .
N13A C14 1.370(3) .
C14 C15 1.359(3) .
C14 H14 0.9500 .
C15 H15 0.9500 .
N21 C22 1.336(3) .
N21 C26 1.336(3) .
N21 I1 2.7985(17) .
C22 C23 1.383(3) .
C22 H22 0.9500 .
C23 C24 1.397(3) .
C23 H23 0.9500 .
C24 C25 1.393(3) .
C25 C26 1.380(3) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C31 C36 1.381(3) .
C31 C32 1.384(3) .
C31 I1 2.090(2) .
C32 F32 1.343(2) .
C32 C36 1.378(3) 3_655
C36 F36 1.344(2) .
C36 C32 1.378(3) 3_655
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
N11A H11 N13A 0.88 2.15 2.882(2) 140.6 1_565
N13B H13 N11B 0.88 2.09 2.882(2) 149.7 1_545
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
C15 N11A C12 N13A 0.4(2) .
C15 N11A C12 C24 -179.77(19) .
N11A C12 N13A C14 -0.8(2) .
C24 C12 N13A C14 179.38(19) .
C12 N13A C14 C15 0.9(2) .
N13A C14 C15 N11A -0.6(2) .
C12 N11A C15 C14 0.1(2) .
C26 N21 C22 C23 -0.7(3) .
I1 N21 C22 C23 153.20(17) .
N21 C22 C23 C24 0.3(3) .
C22 C23 C24 C25 0.4(3) .
C22 C23 C24 C12 -179.33(19) .
N11A C12 C24 C25 26.2(3) .
N13A C12 C24 C25 -154.0(2) .
N11A C12 C24 C23 -154.0(2) .
N13A C12 C24 C23 25.7(3) .
C23 C24 C25 C26 -0.6(3) .
C12 C24 C25 C26 179.10(19) .
C22 N21 C26 C25 0.5(3) .
I1 N21 C26 C25 -150.50(16) .
C24 C25 C26 N21 0.2(3) .
C36 C31 C32 F32 179.30(18) .
I1 C31 C32 F32 -4.0(3) .
C36 C31 C32 C36 -0.5(3) 3_655
I1 C31 C32 C36 176.16(15) 3_655
C32 C31 C36 F36 -178.52(18) .
I1 C31 C36 F36 4.8(3) .
C32 C31 C36 C32 0.5(3) 3_655
I1 C31 C36 C32 -176.13(15) 3_655
