#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:26:07 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180505 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/74/7217403.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_7217403
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 (C4 F8 I2)
;
_chemical_formula_sum            'C20 H14 F8 I2 N6'
_chemical_formula_weight         744.17
_chemical_name_systematic
;
TW-2-07 [2-(3-pyridyl)-imidazole]2, I-(CF2)4-I
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 106.551(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.3500(9)
_cell_length_b                   8.7642(5)
_cell_length_c                   9.9637(6)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      33.81
_cell_measurement_theta_min      2.92
_cell_volume                     1201.18(13)
_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 0.986
_diffrn_measured_fraction_theta_max 0.923
_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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21724
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         33.14
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    2.702
_exptl_absorpt_correction_T_max  0.6717
_exptl_absorpt_correction_T_min  0.4978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.058
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.394
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         4223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0250P)²+1.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0639
_reflns_number_gt                3853
_reflns_number_total             4223
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7216659
_cod_data_source_file            c4ce00803k2.cif
_cod_data_source_block           A2D2
_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_cell_volume        1201.18(12)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7217403
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'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N11 N 0.25062(14) 0.5281(2) 0.53667(19) 0.0245(4) Uani 1 1 d .
C12 C 0.32738(15) 0.6210(2) 0.56137(19) 0.0200(4) Uani 1 1 d .
H12 H 0.3417 0.6830 0.6429 0.024 Uiso 1 1 calc R
C13 C 0.38775(14) 0.6319(2) 0.47405(18) 0.0162(3) Uani 1 1 d .
C14 C 0.36405(16) 0.5432(2) 0.3528(2) 0.0202(4) Uani 1 1 d .
H14 H 0.4027 0.5474 0.2897 0.024 Uiso 1 1 calc R
C15 C 0.28382(17) 0.4492(3) 0.3259(2) 0.0251(4) Uani 1 1 d .
H15 H 0.2659 0.3890 0.2432 0.030 Uiso 1 1 calc R
C16 C 0.22945(17) 0.4435(3) 0.4209(2) 0.0253(4) Uani 1 1 d .
H16 H 0.1751 0.3767 0.4026 0.030 Uiso 1 1 calc R
N21 N 0.52399(12) 0.7745(2) 0.42463(16) 0.0174(3) Uani 1 1 d .
H21 H 0.5125 0.7471 0.3364 0.021 Uiso 0.81(4) 1 calc PR
C22 C 0.47211(14) 0.7321(2) 0.51282(18) 0.0159(3) Uani 1 1 d .
N23 N 0.50926(13) 0.7933(2) 0.63926(16) 0.0185(3) Uani 1 1 d .
H23 H 0.4880 0.7819 0.7133 0.022 Uiso 0.19(4) 1 calc PR
C24 C 0.58755(16) 0.8776(3) 0.6297(2) 0.0215(4) Uani 1 1 d .
H24 H 0.6289 0.9348 0.7041 0.026 Uiso 1 1 calc R
C25 C 0.59745(15) 0.8676(2) 0.4976(2) 0.0203(4) Uani 1 1 d .
H25 H 0.6455 0.9156 0.4634 0.024 Uiso 1 1 calc R
I1 I 0.151865(10) 0.554190(17) 0.744972(13) 0.02315(5) Uani 1 1 d .
C31 C 0.09691(17) 0.6034(3) 0.9200(2) 0.0240(4) Uani 1 1 d .
F31A F 0.05614(13) 0.74157(18) 0.90483(18) 0.0418(4) Uani 1 1 d .
F31B F 0.17208(12) 0.6072(2) 1.03805(15) 0.0412(4) Uani 1 1 d .
C32 C 0.02295(15) 0.4842(2) 0.9398(2) 0.0190(4) Uani 1 1 d .
F32A F -0.04863(11) 0.4753(2) 0.82025(14) 0.0365(4) Uani 1 1 d .
F32B F 0.06900(12) 0.34962(17) 0.96376(17) 0.0354(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_3
C16 N11 C12 118.16(18) .
C16 N11 I1 129.84(15) .
C12 N11 I1 111.96(13) .
N11 C12 C13 123.60(18) .
N11 C12 H12 118.2 .
C13 C12 H12 118.2 .
C14 C13 C12 117.39(18) .
C14 C13 C22 123.05(16) .
C12 C13 C22 119.56(17) .
C15 C14 C13 119.07(18) .
C15 C14 H14 120.5 .
C13 C14 H14 120.5 .
C14 C15 C16 119.3(2) .
C14 C15 H15 120.3 .
C16 C15 H15 120.3 .
N11 C16 C15 122.4(2) .
N11 C16 H16 118.8 .
C15 C16 H16 118.8 .
C22 N21 C25 107.58(15) .
C22 N21 H21 126.2 .
C25 N21 H21 126.2 .
N23 C22 N21 110.89(17) .
N23 C22 C13 124.90(16) .
N21 C22 C13 124.21(16) .
C22 N23 C24 105.44(15) .
C22 N23 H23 127.3 .
C24 N23 H23 127.3 .
C25 C24 N23 110.17(18) .
C25 C24 H24 124.9 .
N23 C24 H24 124.9 .
C24 C25 N21 105.92(17) .
C24 C25 H25 127.0 .
N21 C25 H25 127.0 .
C31 I1 N11 169.70(8) .
F31A C31 F31B 107.0(2) .
F31A C31 C32 109.50(18) .
F31B C31 C32 108.25(17) .
F31A C31 I1 109.87(13) .
F31B C31 I1 108.93(14) .
C32 C31 I1 113.13(14) .
F32A C32 F32B 108.80(18) .
F32A C32 C31 107.92(17) .
F32B C32 C31 107.26(17) .
F32A C32 C32 108.2(2) 3_567
F32B C32 C32 108.5(2) 3_567
C31 C32 C32 116.0(2) 3_567
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C16 1.332(3) .
N11 C12 1.335(3) .
N11 I1 2.8362(18) .
C12 C13 1.395(2) .
C12 H12 0.9500 .
C13 C14 1.395(3) .
C13 C22 1.455(3) .
C14 C15 1.378(3) .
C14 H14 0.9500 .
C15 C16 1.388(3) .
C15 H15 0.9500 .
C16 H16 0.9500 .
N21 C22 1.356(2) .
N21 C25 1.367(3) .
N21 H21 0.8800 .
C22 N23 1.333(2) .
N23 C24 1.371(3) .
N23 H23 0.8800 .
C24 C25 1.366(3) .
C24 H24 0.9500 .
C25 H25 0.9500 .
I1 C31 2.152(2) .
C31 F31A 1.335(3) .
C31 F31B 1.351(3) .
C31 C32 1.541(3) .
C32 F32A 1.336(2) .
C32 F32B 1.340(2) .
C32 C32 1.548(4) 3_567
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
N21 H21 N23 0.88 1.98 2.853(2) 169.2 4_575
N23 H23 N21 0.88 2.08 2.853(2) 146.1 4_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
C16 N11 C12 C13 -1.4(3) .
I1 N11 C12 C13 -179.17(15) .
N11 C12 C13 C14 1.8(3) .
N11 C12 C13 C22 -177.49(19) .
C12 C13 C14 C15 -0.5(3) .
C22 C13 C14 C15 178.69(19) .
C13 C14 C15 C16 -0.9(3) .
C12 N11 C16 C15 -0.3(3) .
I1 N11 C16 C15 177.09(16) .
C14 C15 C16 N11 1.4(4) .
C25 N21 C22 N23 -0.3(2) .
C25 N21 C22 C13 -179.76(18) .
C14 C13 C22 N23 -165.02(19) .
C12 C13 C22 N23 14.2(3) .
C14 C13 C22 N21 14.4(3) .
C12 C13 C22 N21 -166.39(19) .
N21 C22 N23 C24 0.1(2) .
C13 C22 N23 C24 179.56(19) .
C22 N23 C24 C25 0.1(2) .
N23 C24 C25 N21 -0.3(2) .
C22 N21 C25 C24 0.4(2) .
C16 N11 I1 C31 -178.6(4) .
C12 N11 I1 C31 -1.2(5) .
N11 I1 C31 F31A 72.8(5) .
N11 I1 C31 F31B -44.1(5) .
N11 I1 C31 C32 -164.5(3) .
F31A C31 C32 F32A 66.9(2) .
F31B C31 C32 F32A -176.81(18) .
I1 C31 C32 F32A -56.0(2) .
F31A C31 C32 F32B -176.01(17) .
F31B C31 C32 F32B -59.7(2) .
I1 C31 C32 F32B 61.08(19) .
F31A C31 C32 C32 -54.6(3) 3_567
F31B C31 C32 C32 61.6(3) 3_567
I1 C31 C32 C32 -177.55(18) 3_567
