#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:05:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180247 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/33/7113333.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_7113333
loop_
_publ_author_name
'Metrangolo, Pierangelo'
'Präsang, Carsten'
'Resnati, Giuseppe'
'Liantonio, Rosalba'
'Whitwood, Adrian C.'
'Bruce, Duncan W.'
_publ_section_title
;
 Fluorinated liquid crystals formed by halogen bonding.
;
_journal_issue                   31
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3290
_journal_page_last               3292
_journal_paper_doi               10.1039/b605101d
_journal_year                    2006
_chemical_formula_moiety         'C21 H27 N O, 0.5(C6 F12 I2)'
_chemical_formula_sum            'C24 H27 F6 I N O'
_chemical_formula_weight         586.37
_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                105.8320(10)
_cell_angle_beta                 97.4870(10)
_cell_angle_gamma                96.4920(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9751(4)
_cell_length_b                   12.3703(6)
_cell_length_c                   12.7345(6)
_cell_measurement_reflns_used    8772
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.61
_cell_volume                     1183.72(10)
_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, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_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  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13476
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    1.417
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.03; (Sheldrick)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             586
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.172
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         6656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0236
_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)+(0.0345P)²+0.2679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0598
_reflns_number_gt                6211
_reflns_number_total             6656
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b605101d.txt
_cod_data_source_block           dwb0503m
_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/retrospective/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               7113333
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
C1 C -0.1239(2) 0.64049(14) 0.46321(14) 0.0235(3) Uani 1 1 d .
H1 H -0.1853 0.5671 0.4535 0.028 Uiso 1 1 calc R
C2 C -0.0872(2) 0.66948(14) 0.37015(14) 0.0218(3) Uani 1 1 d .
H2 H -0.1230 0.6164 0.2988 0.026 Uiso 1 1 calc R
C3 C 0.00268(19) 0.77687(13) 0.38129(13) 0.0180(3) Uani 1 1 d .
C4 C 0.0525(2) 0.84979(14) 0.48952(13) 0.0199(3) Uani 1 1 d .
H4 H 0.1149 0.9236 0.5022 0.024 Uiso 1 1 calc R
C5 C 0.0100(2) 0.81356(14) 0.57745(14) 0.0215(3) Uani 1 1 d .
H5 H 0.0446 0.8643 0.6500 0.026 Uiso 1 1 calc R
C6 C 0.0402(2) 0.80521(13) 0.28187(13) 0.0193(3) Uani 1 1 d .
H6 H 0.0011 0.7474 0.2137 0.023 Uiso 1 1 calc R
C7 C 0.1232(2) 0.90294(14) 0.27535(13) 0.0199(3) Uani 1 1 d .
H7 H 0.1599 0.9629 0.3422 0.024 Uiso 1 1 calc R
C8 C 0.1613(2) 0.92412(13) 0.17277(13) 0.0184(3) Uani 1 1 d .
C9 C 0.1463(2) 0.83548(13) 0.07442(14) 0.0230(3) Uani 1 1 d .
H9 H 0.1114 0.7594 0.0741 0.028 Uiso 1 1 calc R
C10 C 0.1813(2) 0.85687(14) -0.02186(14) 0.0240(3) Uani 1 1 d .
H10 H 0.1694 0.7956 -0.0877 0.029 Uiso 1 1 calc R
C11 C 0.2339(2) 0.96783(14) -0.02322(13) 0.0199(3) Uani 1 1 d .
C12 C 0.2529(2) 1.05699(14) 0.07371(13) 0.0234(3) Uani 1 1 d .
H12 H 0.2904 1.1328 0.0742 0.028 Uiso 1 1 calc R
C13 C 0.2166(2) 1.03389(14) 0.16989(13) 0.0234(3) Uani 1 1 d .
H13 H 0.2301 1.0951 0.2359 0.028 Uiso 1 1 calc R
C14 C 0.3328(2) 1.08824(14) -0.12923(13) 0.0210(3) Uani 1 1 d .
H14A H 0.4436 1.1172 -0.0785 0.025 Uiso 1 1 calc R
H14B H 0.2531 1.1433 -0.1088 0.025 Uiso 1 1 calc R
C15 C 0.3570(2) 1.07125(14) -0.24821(13) 0.0211(3) Uani 1 1 d .
H15A H 0.2444 1.0424 -0.2969 0.025 Uiso 1 1 calc R
H15B H 0.4315 1.0125 -0.2678 0.025 Uiso 1 1 calc R
C16 C 0.4357(2) 1.17911(13) -0.27055(12) 0.0188(3) Uani 1 1 d .
H16A H 0.5518 1.2056 -0.2260 0.023 Uiso 1 1 calc R
H16B H 0.3652 1.2396 -0.2476 0.023 Uiso 1 1 calc R
C17 C 0.4469(2) 1.15821(14) -0.39302(13) 0.0204(3) Uani 1 1 d .
H17A H 0.5112 1.0943 -0.4161 0.024 Uiso 1 1 calc R
H17B H 0.3296 1.1348 -0.4364 0.024 Uiso 1 1 calc R
C18 C 0.5325(2) 1.26048(13) -0.42149(12) 0.0190(3) Uani 1 1 d .
H18A H 0.6519 1.2820 -0.3813 0.023 Uiso 1 1 calc R
H18B H 0.4713 1.3256 -0.3962 0.023 Uiso 1 1 calc R
C19 C 0.5338(2) 1.23681(14) -0.54516(13) 0.0202(3) Uani 1 1 d .
H19A H 0.5890 1.1688 -0.5708 0.024 Uiso 1 1 calc R
H19B H 0.4141 1.2189 -0.5846 0.024 Uiso 1 1 calc R
C20 C 0.6264(2) 1.33465(14) -0.57655(14) 0.0227(3) Uani 1 1 d .
H20A H 0.7428 1.3578 -0.5320 0.027 Uiso 1 1 calc R
H20B H 0.5643 1.4005 -0.5584 0.027 Uiso 1 1 calc R
C21 C 0.6403(2) 1.30355(17) -0.69894(15) 0.0286(4) Uani 1 1 d .
H21A H 0.7024 1.2387 -0.7173 0.043 Uiso 1 1 calc R
H21B H 0.7022 1.3687 -0.7149 0.043 Uiso 1 1 calc R
H21C H 0.5253 1.2832 -0.7435 0.043 Uiso 1 1 calc R
N1 N -0.07739(18) 0.71057(12) 0.56596(12) 0.0220(3) Uani 1 1 d .
O1 O 0.26324(16) 0.97859(10) -0.12303(9) 0.0238(2) Uani 1 1 d .
C22 C -0.1922(2) 0.53593(14) 0.85741(13) 0.0208(3) Uani 1 1 d .
C23 C -0.3692(2) 0.54747(12) 0.89114(12) 0.0187(3) Uani 1 1 d .
C24 C -0.4059(2) 0.50163(13) 0.98938(12) 0.0189(3) Uani 1 1 d .
F1 F -0.17997(15) 0.42412(9) 0.82134(9) 0.0301(2) Uani 1 1 d .
F2 F -0.07081(14) 0.58231(10) 0.94813(9) 0.0316(2) Uani 1 1 d .
F3 F -0.48822(13) 0.49294(9) 0.80174(8) 0.0245(2) Uani 1 1 d .
F4 F -0.38452(14) 0.65848(8) 0.92061(9) 0.0271(2) Uani 1 1 d .
F5 F -0.36716(15) 0.39615(9) 0.97158(9) 0.0288(2) Uani 1 1 d .
F6 F -0.30209(14) 0.56991(10) 1.08105(8) 0.0304(2) Uani 1 1 d .
I1 I -0.147109(12) 0.616125(8) 0.730258(8) 0.02012(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
N1 C1 C2 123.29(15) .
N1 C1 H1 118.4 .
C2 C1 H1 118.4 .
C1 C2 C3 119.94(15) .
C1 C2 H2 120.0 .
C3 C2 H2 120.0 .
C2 C3 C4 116.51(14) .
C2 C3 C6 118.86(14) .
C4 C3 C6 124.63(14) .
C5 C4 C3 119.52(15) .
C5 C4 H4 120.2 .
C3 C4 H4 120.2 .
N1 C5 C4 123.59(15) .
N1 C5 H5 118.2 .
C4 C5 H5 118.2 .
C7 C6 C3 127.76(15) .
C7 C6 H6 116.1 .
C3 C6 H6 116.1 .
C6 C7 C8 124.79(15) .
C6 C7 H7 117.6 .
C8 C7 H7 117.6 .
C13 C8 C9 117.41(14) .
C13 C8 C7 120.77(14) .
C9 C8 C7 121.81(14) .
C10 C9 C8 121.15(15) .
C10 C9 H9 119.4 .
C8 C9 H9 119.4 .
C9 C10 C11 120.42(15) .
C9 C10 H10 119.8 .
C11 C10 H10 119.8 .
O1 C11 C12 125.29(14) .
O1 C11 C10 115.17(14) .
C12 C11 C10 119.54(14) .
C13 C12 C11 119.24(15) .
C13 C12 H12 120.4 .
C11 C12 H12 120.4 .
C12 C13 C8 122.21(15) .
C12 C13 H13 118.9 .
C8 C13 H13 118.9 .
O1 C14 C15 105.86(12) .
O1 C14 H14A 110.6 .
C15 C14 H14A 110.6 .
O1 C14 H14B 110.6 .
C15 C14 H14B 110.6 .
H14A C14 H14B 108.7 .
C14 C15 C16 113.64(13) .
C14 C15 H15A 108.8 .
C16 C15 H15A 108.8 .
C14 C15 H15B 108.8 .
C16 C15 H15B 108.8 .
H15A C15 H15B 107.7 .
C15 C16 C17 111.14(13) .
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 114.47(13) .
C18 C17 H17A 108.6 .
C16 C17 H17A 108.6 .
C18 C17 H17B 108.6 .
C16 C17 H17B 108.6 .
H17A C17 H17B 107.6 .
C17 C18 C19 112.41(13) .
C17 C18 H18A 109.1 .
C19 C18 H18A 109.1 .
C17 C18 H18B 109.1 .
C19 C18 H18B 109.1 .
H18A C18 H18B 107.9 .
C20 C19 C18 114.13(13) .
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 112.48(14) .
C19 C20 H20A 109.1 .
C21 C20 H20A 109.1 .
C19 C20 H20B 109.1 .
C21 C20 H20B 109.1 .
H20A C20 H20B 107.8 .
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 .
C1 N1 C5 117.15(14) .
C1 N1 I1 114.79(10) .
C5 N1 I1 127.77(11) .
C11 O1 C14 118.62(12) .
F2 C22 F1 107.00(13) .
F2 C22 C23 108.72(13) .
F1 C22 C23 108.62(13) .
F2 C22 I1 109.90(10) .
F1 C22 I1 109.83(10) .
C23 C22 I1 112.61(10) .
F3 C23 F4 108.57(13) .
F3 C23 C22 107.71(12) .
F4 C23 C22 108.32(13) .
F3 C23 C24 109.06(12) .
F4 C23 C24 107.03(12) .
C22 C23 C24 115.96(13) .
F5 C24 F6 108.53(13) .
F5 C24 C23 109.45(12) .
F6 C24 C23 107.30(12) .
F5 C24 C24 108.24(15) 2_467
F6 C24 C24 108.45(15) 2_467
C23 C24 C24 114.72(16) 2_467
C22 I1 N1 177.00(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.335(2) .
C1 C2 1.385(2) .
C1 H1 0.9500 .
C2 C3 1.398(2) .
C2 H2 0.9500 .
C3 C4 1.403(2) .
C3 C6 1.460(2) .
C4 C5 1.381(2) .
C4 H4 0.9500 .
C5 N1 1.342(2) .
C5 H5 0.9500 .
C6 C7 1.340(2) .
C6 H6 0.9500 .
C7 C8 1.463(2) .
C7 H7 0.9500 .
C8 C13 1.391(2) .
C8 C9 1.402(2) .
C9 C10 1.379(2) .
C9 H9 0.9500 .
C10 C11 1.395(2) .
C10 H10 0.9500 .
C11 O1 1.3606(18) .
C11 C12 1.390(2) .
C12 C13 1.389(2) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 O1 1.4329(19) .
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 1.526(2) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.522(2) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.523(2) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.519(2) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.522(2) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
N1 I1 2.7463(14) .
C22 F2 1.3499(19) .
C22 F1 1.3524(19) .
C22 C23 1.539(2) .
C22 I1 2.1640(15) .
C23 F3 1.3440(18) .
C23 F4 1.3454(17) .
C23 C24 1.555(2) .
C24 F5 1.3405(18) .
C24 F6 1.3465(18) .
C24 C24 1.558(3) 2_467
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
N1 C1 C2 C3 -0.1(3) .
C1 C2 C3 C4 0.6(2) .
C1 C2 C3 C6 179.84(15) .
C2 C3 C4 C5 -0.6(2) .
C6 C3 C4 C5 -179.82(15) .
C3 C4 C5 N1 0.2(2) .
C2 C3 C6 C7 179.60(16) .
C4 C3 C6 C7 -1.2(3) .
C3 C6 C7 C8 177.84(15) .
C6 C7 C8 C13 166.99(17) .
C6 C7 C8 C9 -13.9(3) .
C13 C8 C9 C10 -1.5(3) .
C7 C8 C9 C10 179.43(16) .
C8 C9 C10 C11 0.5(3) .
C9 C10 C11 O1 -179.47(16) .
C9 C10 C11 C12 0.8(3) .
O1 C11 C12 C13 179.32(16) .
C10 C11 C12 C13 -1.0(3) .
C11 C12 C13 C8 -0.1(3) .
C9 C8 C13 C12 1.3(3) .
C7 C8 C13 C12 -179.60(16) .
O1 C14 C15 C16 -178.29(13) .
C14 C15 C16 C17 -176.59(14) .
C15 C16 C17 C18 -177.06(13) .
C16 C17 C18 C19 -177.60(13) .
C17 C18 C19 C20 -176.98(14) .
C18 C19 C20 C21 174.29(14) .
C2 C1 N1 C5 -0.4(2) .
C2 C1 N1 I1 -174.62(13) .
C4 C5 N1 C1 0.3(2) .
C4 C5 N1 I1 173.74(12) .
C12 C11 O1 C14 5.4(2) .
C10 C11 O1 C14 -174.31(15) .
C15 C14 O1 C11 177.72(14) .
F2 C22 C23 F3 -175.20(12) .
F1 C22 C23 F3 -59.10(15) .
I1 C22 C23 F3 62.77(13) .
F2 C22 C23 F4 67.55(15) .
F1 C22 C23 F4 -176.35(12) .
I1 C22 C23 F4 -54.48(14) .
F2 C22 C23 C24 -52.74(17) .
F1 C22 C23 C24 63.36(17) .
I1 C22 C23 C24 -174.77(10) .
F3 C23 C24 F5 72.02(16) .
F4 C23 C24 F5 -170.71(13) .
C22 C23 C24 F5 -49.73(17) .
F3 C23 C24 F6 -170.40(12) .
F4 C23 C24 F6 -53.13(16) .
C22 C23 C24 F6 67.85(16) .
F3 C23 C24 C24 -49.9(2) 2_467
F4 C23 C24 C24 67.42(19) 2_467
C22 C23 C24 C24 -171.60(15) 2_467
