#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:15:17 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180471 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/40/7214092.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_7214092
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Wijethunga, Tharanga K.'
'Desper, John'
_publ_section_title
;
 Constructing molecular polygons using halogen bonding and bifurcated
 N-oxides
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              28
_journal_paper_doi               10.1039/c3ce41887a
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety
;
(C8 H12 N2 O2) (C6 F3 I3)2
;
_chemical_formula_sum            'C20 H12 F6 I6 N2 O2'
_chemical_formula_weight         1187.72
_chemical_name_systematic
;
TW-6-15 2,3,5,6-Me4-pyridine-1,4-dioxide, (1,3,5-F3-2,4,6-I3-benzene)2
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.812(3)
_cell_angle_beta                 106.262(2)
_cell_angle_gamma                95.408(3)
_cell_formula_units_Z            1
_cell_length_a                   7.9660(6)
_cell_length_b                   9.2821(7)
_cell_length_c                   10.1097(8)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      33.29
_cell_measurement_theta_min      2.26
_cell_volume                     696.29(9)
_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 0.953
_diffrn_measured_fraction_theta_max 0.842
_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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18582
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         33.13
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    6.755
_exptl_absorpt_correction_T_max  0.4515
_exptl_absorpt_correction_T_min  0.2211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.833
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             534
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.535
_refine_diff_density_min         -0.912
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         4468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0204
_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+0.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0522
_refine_ls_wR_factor_ref         0.0530
_reflns_number_gt                4255
_reflns_number_total             4468
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41887a.txt
_cod_data_source_block           tw1237mA8D3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/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        696.28(9)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7214092
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C11 C 0.7118(3) 0.5175(3) 0.4630(2) 0.0162(4) Uani 1 1 d .
I11 I 0.57832(2) 0.639302(17) 0.324676(16) 0.01707(4) Uani 1 1 d .
C12 C 0.8355(3) 0.5847(3) 0.5912(3) 0.0170(4) Uani 1 1 d .
F12 F 0.8655(2) 0.73319(17) 0.62913(16) 0.0231(3) Uani 1 1 d .
C13 C 0.9296(3) 0.5059(3) 0.6824(2) 0.0167(4) Uani 1 1 d .
I13 I 1.11585(2) 0.613179(17) 0.873884(16) 0.01806(4) Uani 1 1 d .
C14 C 0.8972(3) 0.3522(3) 0.6380(3) 0.0165(4) Uani 1 1 d .
F14 F 0.9839(2) 0.27184(17) 0.72349(17) 0.0231(3) Uani 1 1 d .
C15 C 0.7777(3) 0.2784(3) 0.5097(3) 0.0166(4) Uani 1 1 d .
I15 I 0.73381(2) 0.048603(17) 0.445962(18) 0.02161(5) Uani 1 1 d .
C16 C 0.6852(3) 0.3646(3) 0.4257(3) 0.0166(4) Uani 1 1 d .
F16 F 0.5614(2) 0.29483(17) 0.30455(15) 0.0224(3) Uani 1 1 d .
N21 N 0.4526(3) 0.8893(2) 0.0582(2) 0.0162(4) Uani 1 1 d .
O21 O 0.4028(2) 0.7812(2) 0.11228(19) 0.0207(4) Uani 1 1 d .
C22 C 0.3680(3) 1.0103(3) 0.0637(2) 0.0170(4) Uani 1 1 d .
C26 C 0.5833(3) 0.8763(3) -0.0043(2) 0.0170(4) Uani 1 1 d .
C32 C 0.2313(4) 1.0097(3) 0.1378(3) 0.0230(5) Uani 1 1 d .
H32A H 0.1792 1.1011 0.1362 0.034 Uiso 1 1 calc R
H32B H 0.2860 1.0039 0.2360 0.034 Uiso 1 1 calc R
H32C H 0.1386 0.9236 0.0902 0.034 Uiso 1 1 calc R
C36 C 0.6641(4) 0.7386(3) -0.0022(3) 0.0228(5) Uani 1 1 d .
H36A H 0.7567 0.7414 -0.0486 0.034 Uiso 1 1 calc R
H36B H 0.5728 0.6521 -0.0524 0.034 Uiso 1 1 calc R
H36C H 0.7160 0.7313 0.0960 0.034 Uiso 1 1 calc R
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'
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
C16 C11 C12 117.1(2) . .
C16 C11 I11 120.49(17) . .
C12 C11 I11 122.29(18) . .
C11 I11 O21 173.62(8) . .
F12 C12 C11 118.3(2) . .
F12 C12 C13 118.5(2) . .
C11 C12 C13 123.2(2) . .
C12 C13 C14 116.8(2) . .
C12 C13 I13 121.50(18) . .
C14 C13 I13 121.70(17) . .
C13 I13 O21 170.97(8) . 1_656
F14 C14 C15 118.4(2) . .
F14 C14 C13 118.7(2) . .
C15 C14 C13 122.9(2) . .
C14 C15 C16 117.0(2) . .
C14 C15 I15 121.91(17) . .
C16 C15 I15 121.04(17) . .
C15 I15 I11 170.79(7) . 1_545
F16 C16 C11 119.0(2) . .
F16 C16 C15 118.0(2) . .
C11 C16 C15 123.0(2) . .
O21 N21 C22 118.3(2) . .
O21 N21 C26 119.5(2) . .
C22 N21 C26 122.2(2) . .
N21 O21 I11 134.23(14) . .
N21 C22 C26 118.9(2) . 2_675
N21 C22 C32 115.9(2) . .
C26 C22 C32 125.2(2) 2_675 .
N21 C26 C22 118.9(2) . 2_675
N21 C26 C36 116.4(2) . .
C22 C26 C36 124.7(2) 2_675 .
C22 C32 H32A 109.5 . .
C22 C32 H32B 109.5 . .
H32A C32 H32B 109.5 . .
C22 C32 H32C 109.5 . .
H32A C32 H32C 109.5 . .
H32B C32 H32C 109.5 . .
C26 C36 H36A 109.5 . .
C26 C36 H36B 109.5 . .
H36A C36 H36B 109.5 . .
C26 C36 H36C 109.5 . .
H36A C36 H36C 109.5 . .
H36B C36 H36C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C11 C16 1.379(3) .
C11 C12 1.380(3) .
C11 I11 2.086(2) .
I11 O21 2.8331(16) .
C12 F12 1.339(3) .
C12 C13 1.384(3) .
C13 C14 1.389(3) .
C13 I13 2.081(2) .
I13 O21 2.8809(18) 1_656
C14 F14 1.336(3) .
C14 C15 1.382(3) .
C15 C16 1.386(3) .
C15 I15 2.074(2) .
I15 I11 3.7398(4) 1_545
C16 F16 1.341(3) .
N21 O21 1.310(3) .
N21 C22 1.363(3) .
N21 C26 1.364(3) .
C22 C26 1.382(3) 2_675
C22 C32 1.485(4) .
C26 C22 1.382(3) 2_675
C26 C36 1.485(3) .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
C36 H36A 0.9800 .
C36 H36B 0.9800 .
C36 H36C 0.9800 .
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 C11 I11 O21 -38.7(8) .
C12 C11 I11 O21 138.1(6) .
C16 C11 C12 F12 179.2(2) .
I11 C11 C12 F12 2.3(3) .
C16 C11 C12 C13 -1.0(4) .
I11 C11 C12 C13 -177.86(19) .
F12 C12 C13 C14 -178.8(2) .
C11 C12 C13 C14 1.3(4) .
F12 C12 C13 I13 -0.6(3) .
C11 C12 C13 I13 179.60(19) .
C12 C13 I13 O21 -62.0(6) 1_656
C14 C13 I13 O21 116.1(5) 1_656
C12 C13 C14 F14 -179.3(2) .
I13 C13 C14 F14 2.4(3) .
C12 C13 C14 C15 0.0(4) .
I13 C13 C14 C15 -178.24(19) .
F14 C14 C15 C16 177.7(2) .
C13 C14 C15 C16 -1.6(4) .
F14 C14 C15 I15 -1.1(3) .
C13 C14 C15 I15 179.52(19) .
C14 C15 I15 I11 124.3(4) 1_545
C16 C15 I15 I11 -54.5(5) 1_545
C12 C11 C16 F16 177.5(2) .
I11 C11 C16 F16 -5.6(3) .
C12 C11 C16 C15 -0.8(4) .
I11 C11 C16 C15 176.17(19) .
C14 C15 C16 F16 -176.2(2) .
I15 C15 C16 F16 2.6(3) .
C14 C15 C16 C11 2.0(4) .
I15 C15 C16 C11 -179.12(19) .
C22 N21 O21 I11 -122.5(2) .
C26 N21 O21 I11 58.9(3) .
C11 I11 O21 N21 -93.5(7) .
O21 N21 C22 C26 -178.6(2) 2_675
C26 N21 C22 C26 -0.1(4) 2_675
O21 N21 C22 C32 2.7(3) .
C26 N21 C22 C32 -178.8(2) .
O21 N21 C26 C22 178.6(2) 2_675
C22 N21 C26 C22 0.1(4) 2_675
O21 N21 C26 C36 -1.7(3) .
C22 N21 C26 C36 179.8(2) .
