#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:15:17 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180471 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/40/7214089.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_7214089
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
;
(C6 H7 N O) (C6 F4 I2)
;
_chemical_formula_sum            'C12 H7 F4 I2 N O'
_chemical_formula_weight         510.99
_chemical_name_systematic
;
TW-6-33 4-methylpyridine-N-oxide, 1,2-diiodotetrafluorobenzene
;
_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                89.243(2)
_cell_angle_beta                 83.738(2)
_cell_angle_gamma                65.570(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9400(5)
_cell_length_b                   8.5688(6)
_cell_length_c                   11.5503(8)
_cell_measurement_reflns_used    9047
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.65
_cell_measurement_theta_min      2.61
_cell_volume                     710.77(8)
_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 0.967
_diffrn_measured_fraction_theta_max 0.874
_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  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11235
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         32.57
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    4.463
_exptl_absorpt_correction_T_max  0.5354
_exptl_absorpt_correction_T_min  0.2558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         2.286
_refine_diff_density_min         -0.812
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         4521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0288
_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)+(0.0400P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0768
_reflns_number_gt                4212
_reflns_number_total             4521
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41887a.txt
_cod_data_source_block           tw1246mA5D1
_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_sg_symbol_H-M      P-1
_cod_database_code               7214089
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
N11 N 0.6361(3) 0.2642(3) 0.10518(18) 0.0217(4) Uani 1 1 d .
O11 O 0.5634(3) 0.4243(2) 0.14714(17) 0.0280(4) Uani 1 1 d .
C12 C 0.6170(4) 0.2325(4) -0.0052(2) 0.0273(5) Uani 1 1 d .
H12 H 0.5507 0.3244 -0.0523 0.033 Uiso 1 1 calc R
C13 C 0.6936(5) 0.0668(4) -0.0496(3) 0.0330(6) Uani 1 1 d .
H13 H 0.6787 0.0456 -0.1275 0.040 Uiso 1 1 calc R
C14 C 0.7922(4) -0.0701(4) 0.0164(3) 0.0307(6) Uani 1 1 d .
C17 C 0.8788(6) -0.2517(4) -0.0321(4) 0.0472(9) Uani 1 1 d .
H17A H 0.9055 -0.2516 -0.1170 0.071 Uiso 1 1 calc R
H17B H 0.7925 -0.3057 -0.0128 0.071 Uiso 1 1 calc R
H17C H 0.9949 -0.3160 0.0018 0.071 Uiso 1 1 calc R
C15 C 0.8078(4) -0.0310(4) 0.1295(3) 0.0325(6) Uani 1 1 d .
H15 H 0.8742 -0.1207 0.1782 0.039 Uiso 1 1 calc R
C16 C 0.7291(4) 0.1349(4) 0.1726(2) 0.0289(5) Uani 1 1 d .
H16 H 0.7403 0.1588 0.2507 0.035 Uiso 1 1 calc R
C21 C -0.0096(4) 0.6931(3) 0.4133(2) 0.0209(4) Uani 1 1 d .
I1 I 0.21435(2) 0.56805(2) 0.285933(14) 0.02406(6) Uani 1 1 d .
C22 C -0.1866(4) 0.6947(3) 0.4152(2) 0.0217(4) Uani 1 1 d .
I2 I -0.26692(2) 0.56980(2) 0.292190(14) 0.02390(6) Uani 1 1 d .
C23 C -0.3209(4) 0.7814(4) 0.5070(2) 0.0241(5) Uani 1 1 d .
F23 F -0.4915(2) 0.7864(3) 0.51361(17) 0.0344(4) Uani 1 1 d .
C24 C -0.2837(4) 0.8650(3) 0.5950(2) 0.0249(5) Uani 1 1 d .
F24 F -0.4151(3) 0.9464(3) 0.68269(15) 0.0360(4) Uani 1 1 d .
C25 C -0.1106(4) 0.8637(3) 0.5928(2) 0.0244(5) Uani 1 1 d .
F25 F -0.0725(3) 0.9437(2) 0.67832(15) 0.0340(4) Uani 1 1 d .
C26 C 0.0243(4) 0.7779(4) 0.5027(2) 0.0231(5) Uani 1 1 d .
F26 F 0.1909(3) 0.7812(3) 0.50489(16) 0.0320(4) 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'
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_3
O11 N11 C16 120.0(2) .
O11 N11 C12 119.5(2) .
C16 N11 C12 120.5(2) .
N11 O11 I1 122.02(15) .
N11 C12 C13 119.8(3) .
N11 C12 H12 120.1 .
C13 C12 H12 120.1 .
C12 C13 C14 121.6(3) .
C12 C13 H13 119.2 .
C14 C13 H13 119.2 .
C15 C14 C13 116.4(3) .
C15 C14 C17 121.7(3) .
C13 C14 C17 121.9(3) .
C14 C17 H17A 109.5 .
C14 C17 H17B 109.5 .
H17A C17 H17B 109.5 .
C14 C17 H17C 109.5 .
H17A C17 H17C 109.5 .
H17B C17 H17C 109.5 .
C16 C15 C14 121.1(3) .
C16 C15 H15 119.4 .
C14 C15 H15 119.4 .
N11 C16 C15 120.6(3) .
N11 C16 H16 119.7 .
C15 C16 H16 119.7 .
C26 C21 C22 118.6(2) .
C26 C21 I1 116.24(19) .
C22 C21 I1 125.17(18) .
C21 I1 O11 166.68(8) .
C23 C22 C21 118.6(2) .
C23 C22 I2 116.19(18) .
C21 C22 I2 125.21(18) .
C22 I2 O11 170.30(8) 1_455
F23 C23 C24 117.1(2) .
F23 C23 C22 121.2(2) .
C24 C23 C22 121.7(2) .
F24 C24 C25 119.9(2) .
F24 C24 C23 120.5(2) .
C25 C24 C23 119.6(2) .
F25 C25 C24 120.1(2) .
F25 C25 C26 120.5(2) .
C24 C25 C26 119.4(2) .
F26 C26 C25 116.8(2) .
F26 C26 C21 121.1(2) .
C25 C26 C21 122.1(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 O11 1.324(3) .
N11 C16 1.343(3) .
N11 C12 1.344(3) .
O11 I1 2.833(2) .
C12 C13 1.373(4) .
C12 H12 0.9500 .
C13 C14 1.384(5) .
C13 H13 0.9500 .
C14 C15 1.384(4) .
C14 C17 1.504(4) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C15 C16 1.369(4) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 C26 1.381(4) .
C21 C22 1.398(3) .
C21 I1 2.090(2) .
C22 C23 1.390(4) .
C22 I2 2.091(2) .
I2 O11 2.848(2) 1_455
C23 F23 1.331(3) .
C23 C24 1.377(4) .
C24 F24 1.337(3) .
C24 C25 1.367(4) .
C25 F25 1.338(3) .
C25 C26 1.377(4) .
C26 F26 1.338(3) .
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 O11 I1 -82.3(3) .
C12 N11 O11 I1 98.1(2) .
O11 N11 C12 C13 179.4(3) .
C16 N11 C12 C13 -0.2(4) .
N11 C12 C13 C14 -0.5(5) .
C12 C13 C14 C15 0.6(5) .
C12 C13 C14 C17 -179.1(3) .
C13 C14 C15 C16 0.0(5) .
C17 C14 C15 C16 179.7(3) .
O11 N11 C16 C15 -178.8(3) .
C12 N11 C16 C15 0.8(4) .
C14 C15 C16 N11 -0.7(5) .
C26 C21 I1 O11 3.4(5) .
C22 C21 I1 O11 -175.6(2) .
N11 O11 I1 C21 132.3(3) .
C26 C21 C22 C23 -0.1(4) .
I1 C21 C22 C23 178.92(19) .
C26 C21 C22 I2 -178.17(19) .
I1 C21 C22 I2 0.8(3) .
C23 C22 I2 O11 3.4(6) 1_455
C21 C22 I2 O11 -178.5(3) 1_455
C21 C22 C23 F23 -179.6(2) .
I2 C22 C23 F23 -1.4(3) .
C21 C22 C23 C24 0.1(4) .
I2 C22 C23 C24 178.4(2) .
F23 C23 C24 F24 0.2(4) .
C22 C23 C24 F24 -179.5(2) .
F23 C23 C24 C25 179.8(2) .
C22 C23 C24 C25 0.1(4) .
F24 C24 C25 F25 0.0(4) .
C23 C24 C25 F25 -179.6(2) .
F24 C24 C25 C26 179.3(2) .
C23 C24 C25 C26 -0.3(4) .
F25 C25 C26 F26 -0.8(4) .
C24 C25 C26 F26 179.9(2) .
F25 C25 C26 C21 179.7(2) .
C24 C25 C26 C21 0.3(4) .
C22 C21 C26 F26 -179.7(2) .
I1 C21 C26 F26 1.2(3) .
C22 C21 C26 C25 -0.1(4) .
I1 C21 C26 C25 -179.2(2) .
