#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:18:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180071 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/17/7051774.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_7051774
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 Br2 F4)'
_chemical_formula_sum            'C24 H27 Br F2 N O'
_chemical_formula_weight         463.38
_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                109.606(2)
_cell_angle_beta                 92.273(2)
_cell_angle_gamma                107.571(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6549(7)
_cell_length_b                   12.1014(12)
_cell_length_c                   13.0598(13)
_cell_measurement_reflns_used    5915
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      29.98
_cell_measurement_theta_min      2.83
_cell_volume                     1073.01(18)
_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 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12387
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    1.947
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.03; (Sheldrick)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             478
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         6092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0391P)²+0.1689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0778
_reflns_number_gt                5522
_reflns_number_total             6092
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b709107a.txt
_cod_data_source_block           Bromo_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               7051774
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 0.0358(2) 0.13989(14) 0.27397(13) 0.0232(3) Uani 1 1 d . . .
H1 H 0.0653 0.1089 0.3279 0.028 Uiso 1 1 calc R . .
C2 C 0.0783(2) 0.26743(14) 0.30439(13) 0.0219(3) Uani 1 1 d . . .
H2 H 0.1356 0.3215 0.3773 0.026 Uiso 1 1 calc R . .
C3 C 0.03619(19) 0.31620(13) 0.22701(12) 0.0190(3) Uani 1 1 d . . .
C4 C -0.0456(2) 0.23045(14) 0.12129(12) 0.0224(3) Uani 1 1 d . . .
H4 H -0.0754 0.2583 0.0651 0.027 Uiso 1 1 calc R . .
C5 C -0.0831(2) 0.10444(14) 0.09890(13) 0.0249(3) Uani 1 1 d . . .
H5 H -0.1396 0.0479 0.0266 0.030 Uiso 1 1 calc R . .
C6 C 0.0714(2) 0.44899(14) 0.25191(13) 0.0211(3) Uani 1 1 d . . .
H6 H 0.0465 0.4733 0.1924 0.025 Uiso 1 1 calc R . .
C7 C 0.1356(2) 0.53920(13) 0.35118(12) 0.0211(3) Uani 1 1 d . . .
H7 H 0.1643 0.5146 0.4098 0.025 Uiso 1 1 calc R . .
C8 C 0.1661(2) 0.67203(13) 0.37868(12) 0.0197(3) Uani 1 1 d . . .
C9 C 0.1308(2) 0.72176(14) 0.30038(12) 0.0207(3) Uani 1 1 d . . .
H9 H 0.0888 0.6684 0.2255 0.025 Uiso 1 1 calc R . .
C10 C 0.1559(2) 0.84657(14) 0.33037(12) 0.0211(3) Uani 1 1 d . . .
H10 H 0.1307 0.8785 0.2763 0.025 Uiso 1 1 calc R . .
C11 C 0.2184(2) 0.92690(13) 0.44047(12) 0.0193(3) Uani 1 1 d . . .
C12 C 0.2571(2) 0.88061(14) 0.51945(12) 0.0215(3) Uani 1 1 d . . .
H12 H 0.3015 0.9345 0.5940 0.026 Uiso 1 1 calc R . .
C13 C 0.2297(2) 0.75377(14) 0.48758(12) 0.0214(3) Uani 1 1 d . . .
H13 H 0.2550 0.7219 0.5417 0.026 Uiso 1 1 calc R . .
C14 C 0.2958(2) 1.13652(13) 0.57094(12) 0.0212(3) Uani 1 1 d . . .
H14A H 0.4211 1.1418 0.5993 0.025 Uiso 1 1 calc R . .
H14B H 0.2088 1.1127 0.6201 0.025 Uiso 1 1 calc R . .
C15 C 0.2986(2) 1.25947(13) 0.56427(12) 0.0215(3) Uani 1 1 d . . .
H15A H 0.1717 1.2512 0.5357 0.026 Uiso 1 1 calc R . .
H15B H 0.3800 1.2778 0.5108 0.026 Uiso 1 1 calc R . .
C16 C 0.3655(2) 1.36908(13) 0.67348(12) 0.0209(3) Uani 1 1 d . . .
H16A H 0.4882 1.3742 0.7059 0.025 Uiso 1 1 calc R . .
H16B H 0.2776 1.3558 0.7253 0.025 Uiso 1 1 calc R . .
C17 C 0.3811(2) 1.49095(14) 0.65796(12) 0.0214(3) Uani 1 1 d . . .
H17A H 0.4709 1.5039 0.6071 0.026 Uiso 1 1 calc R . .
H17B H 0.2590 1.4834 0.6227 0.026 Uiso 1 1 calc R . .
C18 C 0.4421(2) 1.60500(13) 0.76403(12) 0.0205(3) Uani 1 1 d . . .
H18A H 0.5649 1.6136 0.7992 0.025 Uiso 1 1 calc R . .
H18B H 0.3527 1.5925 0.8153 0.025 Uiso 1 1 calc R . .
C19 C 0.4546(2) 1.72472(13) 0.74525(12) 0.0198(3) Uani 1 1 d . . .
H19A H 0.5297 1.7305 0.6860 0.024 Uiso 1 1 calc R . .
H19B H 0.3284 1.7201 0.7194 0.024 Uiso 1 1 calc R . .
C20 C 0.5395(2) 1.84244(14) 0.84658(13) 0.0229(3) Uani 1 1 d . . .
H20A H 0.6666 1.8484 0.8724 0.027 Uiso 1 1 calc R . .
H20B H 0.4650 1.8375 0.9061 0.027 Uiso 1 1 calc R . .
C21 C 0.5479(3) 1.95901(15) 0.82319(15) 0.0315(4) Uani 1 1 d . . .
H21A H 0.6155 1.9617 0.7614 0.047 Uiso 1 1 calc R . .
H21B H 0.6119 2.0330 0.8886 0.047 Uiso 1 1 calc R . .
H21C H 0.4216 1.9573 0.8045 0.047 Uiso 1 1 calc R . .
N1 N -0.04444(18) 0.05781(12) 0.17291(12) 0.0252(3) Uani 1 1 d . . .
O1 O 0.23540(16) 1.04773(10) 0.46015(9) 0.0236(2) Uani 1 1 d . . .
Br1 Br -0.25085(2) -0.202619(12) 0.104483(11) 0.02206(5) Uani 1 1 d . . .
C22 C -0.3939(2) -0.37228(13) 0.04584(11) 0.0194(3) Uani 1 1 d . . .
C23 C -0.5859(2) -0.41214(14) 0.03185(12) 0.0207(3) Uani 1 1 d . . .
C24 C -0.3104(2) -0.46327(14) 0.01304(12) 0.0205(3) Uani 1 1 d . . .
F1 F -0.67430(13) -0.32856(9) 0.06065(8) 0.0285(2) Uani 1 1 d . . .
F2 F -0.12446(12) -0.43017(9) 0.02568(8) 0.0279(2) 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'
Br Br -0.2901 2.4595 '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
N1 C1 C2 123.73(14) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 119.62(14) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 116.52(13) . . ?
C4 C3 C6 119.80(13) . . ?
C2 C3 C6 123.68(13) . . ?
C5 C4 C3 119.56(14) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 123.93(14) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C7 C6 C3 125.70(14) . . ?
C7 C6 H6 117.1 . . ?
C3 C6 H6 117.1 . . ?
C6 C7 C8 126.65(14) . . ?
C6 C7 H7 116.7 . . ?
C8 C7 H7 116.7 . . ?
C13 C8 C9 117.71(13) . . ?
C13 C8 C7 119.34(13) . . ?
C9 C8 C7 122.93(13) . . ?
C10 C9 C8 121.04(13) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 120.30(13) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
O1 C11 C12 125.24(13) . . ?
O1 C11 C10 114.84(12) . . ?
C12 C11 C10 119.92(13) . . ?
C11 C12 C13 118.93(13) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C12 C13 C8 122.09(13) . . ?
C12 C13 H13 119.0 . . ?
C8 C13 H13 119.0 . . ?
O1 C14 C15 105.39(12) . . ?
O1 C14 H14A 110.7 . . ?
C15 C14 H14A 110.7 . . ?
O1 C14 H14B 110.7 . . ?
C15 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C14 C15 C16 114.32(12) . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 C17 111.05(12) . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C18 C17 C16 114.38(12) . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C16 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 C19 112.81(12) . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 C18 114.24(12) . . ?
C20 C19 H19A 108.7 . . ?
C18 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 C21 111.97(13) . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C5 N1 C1 116.62(13) . . ?
C5 N1 Br1 111.18(10) . . ?
C1 N1 Br1 129.16(10) . . ?
C11 O1 C14 118.80(11) . . ?
C22 Br1 N1 174.11(5) . . ?
C23 C22 C24 117.27(13) . . ?
C23 C22 Br1 121.72(11) . . ?
C24 C22 Br1 121.00(11) . . ?
F1 C23 C24 118.77(13) . 2_445 ?
F1 C23 C22 119.97(13) . . ?
C24 C23 C22 121.25(13) 2_445 . ?
F2 C24 C23 118.61(13) . 2_445 ?
F2 C24 C22 119.91(13) . . ?
C23 C24 C22 121.47(13) 2_445 . ?
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 N1 1.339(2) . ?
C1 C2 1.386(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.401(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(2) . ?
C3 C6 1.4634(19) . ?
C4 C5 1.387(2) . ?
C4 H4 0.9500 . ?
C5 N1 1.336(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.338(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.465(2) . ?
C7 H7 0.9500 . ?
C8 C13 1.396(2) . ?
C8 C9 1.404(2) . ?
C9 C10 1.376(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.403(2) . ?
C10 H10 0.9500 . ?
C11 O1 1.3607(17) . ?
C11 C12 1.389(2) . ?
C12 C13 1.394(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O1 1.4372(17) . ?
C14 C15 1.513(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.523(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.525(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.523(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.525(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.520(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.524(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N1 Br1 2.8668(13) . ?
Br1 C22 1.8766(14) . ?
C22 C23 1.385(2) . ?
C22 C24 1.391(2) . ?
C23 F1 1.3418(16) . ?
C23 C24 1.376(2) 2_445 ?
C24 F2 1.3441(16) . ?
C24 C23 1.376(2) 2_445 ?
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
N1 C1 C2 C3 0.2(2) . . . . ?
C1 C2 C3 C4 -0.9(2) . . . . ?
C1 C2 C3 C6 178.45(13) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C6 C3 C4 C5 -178.32(14) . . . . ?
C3 C4 C5 N1 -0.5(2) . . . . ?
C4 C3 C6 C7 174.67(14) . . . . ?
C2 C3 C6 C7 -4.6(2) . . . . ?
C3 C6 C7 C8 -177.87(14) . . . . ?
C6 C7 C8 C13 178.35(15) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C13 C8 C9 C10 -0.8(2) . . . . ?
C7 C8 C9 C10 177.95(14) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C9 C10 C11 O1 -179.12(13) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
O1 C11 C12 C13 178.70(14) . . . . ?
C10 C11 C12 C13 -1.1(2) . . . . ?
C11 C12 C13 C8 0.6(2) . . . . ?
C9 C8 C13 C12 0.4(2) . . . . ?
C7 C8 C13 C12 -178.42(14) . . . . ?
O1 C14 C15 C16 -178.11(12) . . . . ?
C14 C15 C16 C17 174.81(13) . . . . ?
C15 C16 C17 C18 178.34(12) . . . . ?
C16 C17 C18 C19 -179.60(12) . . . . ?
C17 C18 C19 C20 -172.23(12) . . . . ?
C18 C19 C20 C21 -179.75(13) . . . . ?
C4 C5 N1 C1 -0.2(2) . . . . ?
C4 C5 N1 Br1 161.88(13) . . . . ?
C2 C1 N1 C5 0.4(2) . . . . ?
C2 C1 N1 Br1 -157.93(11) . . . . ?
C12 C11 O1 C14 -0.8(2) . . . . ?
C10 C11 O1 C14 179.02(13) . . . . ?
C15 C14 O1 C11 -179.66(12) . . . . ?
C24 C22 C23 F1 -179.14(13) . . . . ?
Br1 C22 C23 F1 -0.08(19) . . . . ?
C24 C22 C23 C24 -0.2(2) . . . 2_445 ?
Br1 C22 C23 C24 178.84(11) . . . 2_445 ?
C23 C22 C24 F2 -179.32(13) . . . . ?
Br1 C22 C24 F2 1.62(19) . . . . ?
C23 C22 C24 C23 0.2(2) . . . 2_445 ?
Br1 C22 C24 C23 -178.85(11) . . . 2_445 ?
