#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:26:07 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180505 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/74/7217414.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_7217414
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
;
(C7 H6 N4)2 (C6 F3 I3)
;
_chemical_formula_sum            'C20 H12 F3 I3 N8'
_chemical_formula_weight         802.08
_chemical_name_systematic
;
TW-1-59 [2-(2-pyrazinyl)-imidazole]2, 1,3,5-F3-2,4,6-I3-benzene
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   33.0655(16)
_cell_length_b                   9.8284(5)
_cell_length_c                   7.3176(3)
_cell_measurement_reflns_used    9054
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.44
_cell_measurement_theta_min      2.46
_cell_volume                     2378.08(19)
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            36207
_diffrn_reflns_theta_full        32.52
_diffrn_reflns_theta_max         32.52
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    3.993
_exptl_absorpt_correction_T_max  0.8566
_exptl_absorpt_correction_T_min  0.4010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         4246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0212
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0200P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0460
_refine_ls_wR_factor_ref         0.0480
_reflns_number_gt                3689
_reflns_number_total             4246
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7216670
_cod_data_source_file            c4ce00803k2.cif
_cod_data_source_block           A4D9
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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      Pbcn
_cod_database_code               7217414
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11A N 0.75884(4) -0.11260(13) 0.2832(2) 0.0159(3) Uani 0.80(3) 1 d P A 1
H11 H 0.7502 -0.1970 0.2927 0.019 Uiso 0.80(3) 1 calc PR A 1
N11B N 0.75884(4) -0.11260(13) 0.2832(2) 0.0159(3) Uani 0.20(3) 1 d P A 2
C12 C 0.73849(5) 0.00044(15) 0.3322(2) 0.0142(3) Uani 1 1 d . . .
N13A N 0.76000(4) 0.11177(13) 0.2995(2) 0.0160(3) Uani 0.80(3) 1 d P A 1
N13B N 0.76000(4) 0.11177(13) 0.2995(2) 0.0160(3) Uani 0.20(3) 1 d P A 2
H13 H 0.7528 0.1966 0.3197 0.019 Uiso 0.20(3) 1 calc PR A 2
C14 C 0.79559(5) 0.06687(17) 0.2281(2) 0.0181(3) Uani 1 1 d . . .
H14 H 0.8174 0.1236 0.1918 0.022 Uiso 1 1 calc R A 1
C15 C 0.79532(5) -0.07188(17) 0.2163(2) 0.0183(3) Uani 1 1 d . A .
H15 H 0.8163 -0.1285 0.1706 0.022 Uiso 1 1 calc R B 1
N21 N 0.67968(5) -0.12185(15) 0.4304(2) 0.0196(3) Uani 1 1 d . . .
C22 C 0.69786(5) -0.00119(16) 0.4092(2) 0.0149(3) Uani 1 1 d . A .
C23 C 0.67856(5) 0.11993(17) 0.4570(2) 0.0184(3) Uani 1 1 d . . .
H23 H 0.6928 0.2033 0.4439 0.022 Uiso 1 1 calc R A .
N24 N 0.64105(5) 0.12230(16) 0.5200(2) 0.0222(3) Uani 1 1 d . A .
C25 C 0.62257(6) 0.0019(2) 0.5383(3) 0.0240(4) Uani 1 1 d . . .
H25 H 0.5955 -0.0010 0.5817 0.029 Uiso 1 1 calc R A .
C26 C 0.64209(6) -0.11860(19) 0.4953(3) 0.0225(3) Uani 1 1 d . A .
H26 H 0.6281 -0.2021 0.5129 0.027 Uiso 1 1 calc R . .
C31 C 0.5000 0.6707(2) 0.7500 0.0192(5) Uani 1 2 d S . .
I31 I 0.5000 0.881980(18) 0.7500 0.03018(5) Uani 1 2 d S . .
C32 C 0.53344(5) 0.59792(18) 0.6921(2) 0.0187(3) Uani 1 1 d . . .
F32 F 0.56590(4) 0.66608(11) 0.63251(15) 0.0251(2) Uani 1 1 d . . .
C33 C 0.53476(5) 0.45699(18) 0.6936(2) 0.0179(3) Uani 1 1 d . A .
I33 I 0.585169(3) 0.343306(12) 0.616810(16) 0.02156(4) Uani 1 1 d . . .
C34 C 0.5000 0.3906(2) 0.7500 0.0177(4) Uani 1 2 d S . .
F34 F 0.5000 0.25441(15) 0.7500 0.0253(3) Uani 0.50 1 d P A .
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 107.20(13) . .
C12 N11A H11 126.4 . .
C15 N11A H11 126.4 . .
N13A C12 N11A 111.36(14) . .
N13A C12 C22 124.97(14) . .
N11A C12 C22 123.66(14) . .
C12 N13A C14 105.39(13) . .
N13A C14 C15 110.00(15) . .
N13A C14 H14 125.0 . .
C15 C14 H14 125.0 . .
N11A C15 C14 106.04(15) . .
N11A C15 H15 127.0 . .
C14 C15 H15 127.0 . .
C26 N21 C22 116.07(15) . .
N21 C22 C23 121.43(15) . .
N21 C22 C12 117.95(14) . .
C23 C22 C12 120.62(15) . .
N24 C23 C22 122.07(16) . .
N24 C23 H23 119.0 . .
C22 C23 H23 119.0 . .
C23 N24 C25 116.56(16) . .
C23 N24 I33 133.34(12) . .
C25 N24 I33 110.03(12) . .
N24 C25 C26 121.36(17) . .
N24 C25 H25 119.3 . .
C26 C25 H25 119.3 . .
N21 C26 C25 122.47(17) . .
N21 C26 H26 118.8 . .
C25 C26 H26 118.8 . .
C32 C31 C32 117.8(2) 3_656 .
C32 C31 I31 121.12(11) 3_656 .
C32 C31 I31 121.12(11) . .
F32 C32 C31 118.83(16) . .
F32 C32 C33 118.53(16) . .
C31 C32 C33 122.64(17) . .
C34 C33 C32 116.56(17) . .
C34 C33 I33 119.45(13) . .
C32 C33 I33 123.99(13) . .
C33 I33 N24 164.66(6) . .
F34 C34 C33 118.11(11) . .
F34 C34 C33 118.11(11) . 3_656
C33 C34 C33 123.8(2) . 3_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11A C12 1.348(2) .
N11A C15 1.362(2) .
N11A H11 0.8800 .
C12 N13A 1.327(2) .
C12 C22 1.457(2) .
N13A C14 1.361(2) .
C14 C15 1.366(2) .
C14 H14 0.9500 .
C15 H15 0.9500 .
N21 C26 1.331(2) .
N21 C22 1.338(2) .
C22 C23 1.395(2) .
C23 N24 1.323(2) .
C23 H23 0.9500 .
N24 C25 1.339(2) .
N24 I33 2.9383(15) .
C25 C26 1.385(3) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C31 C32 1.383(2) 3_656
C31 C32 1.383(2) .
C31 I31 2.077(2) .
C32 F32 1.338(2) .
C32 C33 1.386(2) .
C33 C34 1.385(2) .
C33 I33 2.0837(17) .
C34 F34 1.338(3) .
C34 C33 1.385(2) 3_656
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 1.91 2.7823(18) 170.6 8_755
N13B H13 N11B 0.88 1.93 2.7823(18) 161.9 8_765
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_4
C15 N11A C12 N13A 0.23(19) . .
C15 N11A C12 C22 179.56(15) . .
N11A C12 N13A C14 -0.48(19) . .
C22 C12 N13A C14 -179.80(15) . .
C12 N13A C14 C15 0.6(2) . .
C12 N11A C15 C14 0.13(19) . .
N13A C14 C15 N11A -0.4(2) . .
C26 N21 C22 C23 1.5(3) . .
C26 N21 C22 C12 -177.82(15) . .
N13A C12 C22 N21 178.53(16) . .
N11A C12 C22 N21 -0.7(2) . .
N13A C12 C22 C23 -0.8(3) . .
N11A C12 C22 C23 179.98(16) . .
N21 C22 C23 N24 -2.2(3) . .
C12 C22 C23 N24 177.12(16) . .
C22 C23 N24 C25 0.9(3) . .
C22 C23 N24 I33 -175.41(12) . .
C23 N24 C25 C26 0.8(3) . .
I33 N24 C25 C26 177.95(15) . .
C22 N21 C26 C25 0.2(3) . .
N24 C25 C26 N21 -1.4(3) . .
C32 C31 C32 F32 178.85(18) 3_656 .
I31 C31 C32 F32 -1.15(18) . .
C32 C31 C32 C33 -1.26(12) 3_656 .
I31 C31 C32 C33 178.74(12) . .
F32 C32 C33 C34 -177.72(13) . .
C31 C32 C33 C34 2.4(2) . .
F32 C32 C33 I33 2.2(2) . .
C31 C32 C33 I33 -177.66(10) . .
C32 C33 C34 F34 178.85(11) . .
I33 C33 C34 F34 -1.09(13) . .
C32 C33 C34 C33 -1.15(11) . 3_656
I33 C33 C34 C33 178.91(13) . 3_656
