#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:18:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180071 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/17/7051773.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_7051773
loop_
_publ_author_name
'Bruce, Duncan W.'
'Metrangolo, Pierangelo'
'Meyer, Franck'
'Präsang, Carsten'
'Resnati, Giuseppe'
'Terraneo, Giancarlo'
'Whitwood, Adrian C.'
_publ_section_title
;
 Mesogenic, trimeric, halogen-bonded complexes from alkoxystilbazoles
 and 1,4-diiodotetrafluorobenzene
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              477
_journal_paper_doi               10.1039/b709107a
_journal_volume                  32
_journal_year                    2008
_chemical_formula_moiety         'C21 H27 N O, 0.5(C6 F4 I2)'
_chemical_formula_sum            'C24 H27 F2 I N O'
_chemical_formula_weight         510.37
_chemical_name_systematic
;
?
;
_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                114.368(2)
_cell_angle_beta                 91.703(2)
_cell_angle_gamma                106.360(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6014(8)
_cell_length_b                   12.5366(13)
_cell_length_c                   13.2340(14)
_cell_measurement_reflns_used    6050
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.83
_cell_volume                     1086.8(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11209
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    1.505
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.03; (Sheldrick)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             514
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.982
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         5337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0237
_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)+(0.0288P)²+0.1918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0570
_reflns_number_gt                4888
_reflns_number_total             5337
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b709107a.txt
_cod_data_source_block           Iodo_LC_3-8
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7051773
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6013(3) 0.12773(17) 0.04439(15) 0.0188(4) Uani 1 1 d . . .
C2 C 0.6893(3) 0.03844(18) 0.01472(16) 0.0193(4) Uani 1 1 d . . .
C3 C 0.5908(3) -0.08516(18) -0.02806(16) 0.0196(4) Uani 1 1 d . . .
F1 F 0.87656(16) 0.07334(11) 0.02821(11) 0.0277(3) Uani 1 1 d . . .
F2 F 0.68663(16) -0.16589(11) -0.05283(10) 0.0266(3) Uani 1 1 d . . .
I1 I 0.752119(17) 0.316364(11) 0.108098(10) 0.01967(5) Uani 1 1 d . . .
C4 C 0.0291(3) -0.34398(18) 0.27985(16) 0.0211(4) Uani 1 1 d . . .
H4 H 0.0592 -0.3702 0.3341 0.025 Uiso 1 1 calc R . .
C5 C 0.0796(3) -0.21849(18) 0.31074(16) 0.0204(4) Uani 1 1 d . . .
H5 H 0.1429 -0.1608 0.3846 0.025 Uiso 1 1 calc R . .
C6 C 0.0376(3) -0.17661(18) 0.23340(16) 0.0187(4) Uani 1 1 d . . .
C7 C -0.0527(3) -0.26742(18) 0.12584(16) 0.0213(4) Uani 1 1 d . . .
H7 H -0.0823 -0.2444 0.0692 0.026 Uiso 1 1 calc R . .
C8 C -0.0986(3) -0.39080(18) 0.10270(17) 0.0230(4) Uani 1 1 d . . .
H8 H -0.1610 -0.4508 0.0293 0.028 Uiso 1 1 calc R . .
C9 C 0.0786(3) -0.04641(18) 0.25798(17) 0.0206(4) Uani 1 1 d . . .
H9 H 0.0531 -0.0292 0.1966 0.025 Uiso 1 1 calc R . .
C10 C 0.1485(3) 0.05092(18) 0.35836(16) 0.0197(4) Uani 1 1 d . . .
H10 H 0.1805 0.0342 0.4190 0.024 Uiso 1 1 calc R . .
C11 C 0.1801(3) 0.18053(17) 0.38346(16) 0.0182(4) Uani 1 1 d . . .
C12 C 0.1471(3) 0.21848(18) 0.30051(16) 0.0208(4) Uani 1 1 d . . .
H12 H 0.1083 0.1588 0.2241 0.025 Uiso 1 1 calc R . .
C13 C 0.1699(3) 0.34045(18) 0.32823(16) 0.0200(4) Uani 1 1 d . . .
H13 H 0.1480 0.3644 0.2709 0.024 Uiso 1 1 calc R . .
C14 C 0.2251(3) 0.42947(17) 0.43997(16) 0.0182(4) Uani 1 1 d . . .
C15 C 0.2641(3) 0.39534(18) 0.52364(16) 0.0197(4) Uani 1 1 d . . .
H15 H 0.3062 0.4557 0.5996 0.024 Uiso 1 1 calc R . .
C16 C 0.2403(3) 0.27176(18) 0.49420(16) 0.0192(4) Uani 1 1 d . . .
H16 H 0.2660 0.2484 0.5514 0.023 Uiso 1 1 calc R . .
C17 C 0.2923(3) 0.64267(17) 0.57084(15) 0.0192(4) Uani 1 1 d . . .
H17A H 0.4181 0.6513 0.6024 0.023 Uiso 1 1 calc R . .
H17B H 0.2040 0.6241 0.6195 0.023 Uiso 1 1 calc R . .
C18 C 0.2919(3) 0.75970(18) 0.56359(16) 0.0204(4) Uani 1 1 d . . .
H18A H 0.1640 0.7492 0.5339 0.025 Uiso 1 1 calc R . .
H18B H 0.3724 0.7716 0.5091 0.025 Uiso 1 1 calc R . .
C19 C 0.3586(3) 0.87568(17) 0.67494(16) 0.0192(4) Uani 1 1 d . . .
H19A H 0.4811 0.8826 0.7095 0.023 Uiso 1 1 calc R . .
H19B H 0.2697 0.8696 0.7271 0.023 Uiso 1 1 calc R . .
C20 C 0.3751(3) 0.99071(17) 0.65728(16) 0.0197(4) Uani 1 1 d . . .
H20A H 0.4616 0.9942 0.6034 0.024 Uiso 1 1 calc R . .
H20B H 0.2518 0.9822 0.6225 0.024 Uiso 1 1 calc R . .
C21 C 0.4431(3) 1.11218(17) 0.76343(16) 0.0194(4) Uani 1 1 d . . .
H21A H 0.5667 1.1218 0.7988 0.023 Uiso 1 1 calc R . .
H21B H 0.3562 1.1103 0.8174 0.023 Uiso 1 1 calc R . .
C22 C 0.4574(3) 1.22259(18) 0.73915(15) 0.0193(4) Uani 1 1 d . . .
H22A H 0.5262 1.2155 0.6755 0.023 Uiso 1 1 calc R . .
H22B H 0.3305 1.2190 0.7151 0.023 Uiso 1 1 calc R . .
C23 C 0.5535(3) 1.34789(18) 0.83805(16) 0.0210(4) Uani 1 1 d . . .
H23A H 0.4837 1.3567 0.9014 0.025 Uiso 1 1 calc R . .
H23B H 0.6803 1.3520 0.8631 0.025 Uiso 1 1 calc R . .
C24 C 0.5665(3) 1.45420(19) 0.80791(19) 0.0278(4) Uani 1 1 d . . .
H24A H 0.6337 1.4451 0.7444 0.042 Uiso 1 1 calc R . .
H24B H 0.6331 1.5328 0.8728 0.042 Uiso 1 1 calc R . .
H24C H 0.4410 1.4532 0.7871 0.042 Uiso 1 1 calc R . .
N1 N -0.0604(2) -0.43070(15) 0.17715(14) 0.0226(3) Uani 1 1 d . . .
O1 O 0.2367(2) 0.54623(12) 0.45774(11) 0.0211(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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C3 C1 C2 116.39(17) 2_655 . ?
C3 C1 I1 121.98(14) 2_655 . ?
C2 C1 I1 121.62(14) . . ?
F1 C2 C3 118.69(17) . . ?
F1 C2 C1 119.60(17) . . ?
C3 C2 C1 121.71(17) . . ?
F2 C3 C2 118.11(17) . . ?
F2 C3 C1 119.98(17) . 2_655 ?
C2 C3 C1 121.90(17) . 2_655 ?
N1 C4 C5 123.33(18) . . ?
N1 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
C4 C5 C6 119.93(18) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 116.51(18) . . ?
C5 C6 C9 124.59(18) . . ?
C7 C6 C9 118.90(18) . . ?
C8 C7 C6 119.52(18) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
N1 C8 C7 123.90(18) . . ?
N1 C8 H8 118.0 . . ?
C7 C8 H8 118.0 . . ?
C10 C9 C6 126.45(19) . . ?
C10 C9 H9 116.8 . . ?
C6 C9 H9 116.8 . . ?
C9 C10 C11 126.11(18) . . ?
C9 C10 H10 116.9 . . ?
C11 C10 H10 116.9 . . ?
C16 C11 C12 117.44(17) . . ?
C16 C11 C10 119.79(17) . . ?
C12 C11 C10 122.74(17) . . ?
C13 C12 C11 121.02(17) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.50(18) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
O1 C14 C15 124.91(17) . . ?
O1 C14 C13 115.27(16) . . ?
C15 C14 C13 119.82(17) . . ?
C16 C15 C14 118.90(17) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C11 122.27(18) . . ?
C15 C16 H16 118.9 . . ?
C11 C16 H16 118.9 . . ?
O1 C17 C18 106.02(15) . . ?
O1 C17 H17A 110.5 . . ?
C18 C17 H17A 110.5 . . ?
O1 C17 H17B 110.5 . . ?
C18 C17 H17B 110.5 . . ?
H17A C17 H17B 108.7 . . ?
C17 C18 C19 114.41(16) . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 C20 110.70(15) . . ?
C18 C19 H19A 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C21 C20 C19 114.97(16) . . ?
C21 C20 H20A 108.5 . . ?
C19 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
C19 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C20 C21 C22 111.97(15) . . ?
C20 C21 H21A 109.2 . . ?
C22 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
C22 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C23 C22 C21 114.61(16) . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22B 108.6 . . ?
C21 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C24 C23 C22 112.07(17) . . ?
C24 C23 H23A 109.2 . . ?
C22 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
C22 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C8 N1 C4 116.80(17) . . ?
C14 O1 C17 118.33(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.382(3) 2_655 ?
C1 C2 1.389(3) . ?
C1 I1 2.0946(19) . ?
C2 F1 1.349(2) . ?
C2 C3 1.371(3) . ?
C3 F2 1.349(2) . ?
C3 C1 1.382(3) 2_655 ?
C4 N1 1.342(2) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(3) . ?
C6 C9 1.462(3) . ?
C7 C8 1.381(3) . ?
C7 H7 0.9500 . ?
C8 N1 1.333(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.338(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.462(3) . ?
C10 H10 0.9500 . ?
C11 C16 1.396(3) . ?
C11 C12 1.406(3) . ?
C12 C13 1.373(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(3) . ?
C13 H13 0.9500 . ?
C14 O1 1.359(2) . ?
C14 C15 1.393(3) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O1 1.436(2) . ?
C17 C18 1.510(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.521(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.526(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.519(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.522(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.521(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.521(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 F1 179.89(17) 2_655 . . . ?
I1 C1 C2 F1 0.8(2) . . . . ?
C3 C1 C2 C3 -0.2(3) 2_655 . . . ?
I1 C1 C2 C3 -179.33(14) . . . . ?
F1 C2 C3 F2 1.1(3) . . . . ?
C1 C2 C3 F2 -178.78(17) . . . . ?
F1 C2 C3 C1 -179.88(17) . . . 2_655 ?
C1 C2 C3 C1 0.2(3) . . . 2_655 ?
N1 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C7 -1.1(3) . . . . ?
C4 C5 C6 C9 177.80(18) . . . . ?
C5 C6 C7 C8 1.4(3) . . . . ?
C9 C6 C7 C8 -177.57(18) . . . . ?
C6 C7 C8 N1 -0.7(3) . . . . ?
C5 C6 C9 C10 -5.3(3) . . . . ?
C7 C6 C9 C10 173.62(19) . . . . ?
C6 C9 C10 C11 -176.61(18) . . . . ?
C9 C10 C11 C16 174.94(19) . . . . ?
C9 C10 C11 C12 -3.1(3) . . . . ?
C16 C11 C12 C13 -1.2(3) . . . . ?
C10 C11 C12 C13 176.84(18) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C12 C13 C14 O1 -177.72(18) . . . . ?
C12 C13 C14 C15 2.4(3) . . . . ?
O1 C14 C15 C16 177.79(18) . . . . ?
C13 C14 C15 C16 -2.4(3) . . . . ?
C14 C15 C16 C11 0.5(3) . . . . ?
C12 C11 C16 C15 1.3(3) . . . . ?
C10 C11 C16 C15 -176.86(18) . . . . ?
O1 C17 C18 C19 -176.61(15) . . . . ?
C17 C18 C19 C20 173.36(17) . . . . ?
C18 C19 C20 C21 -179.31(16) . . . . ?
C19 C20 C21 C22 179.58(16) . . . . ?
C20 C21 C22 C23 -170.67(16) . . . . ?
C21 C22 C23 C24 179.00(17) . . . . ?
C7 C8 N1 C4 -0.5(3) . . . . ?
C5 C4 N1 C8 0.8(3) . . . . ?
C15 C14 O1 C17 -0.3(3) . . . . ?
C13 C14 O1 C17 179.87(16) . . . . ?
C18 C17 O1 C14 -179.94(16) . . . . ?
