#------------------------------------------------------------------------------
#$Date: 2016-03-26 01:55:57 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180115 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/13/7101322.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_7101322
loop_
_publ_author_name
'Duncan Bruce'
'Rosalba Liantonio'
'Pierangelo Metrangolo'
'Carsten Prasang'
'Giuseppe Resnati'
'Adrian C. Whitwood'
_publ_section_title
;
Fluorinated liquid crystals formed by halogen bonding
;
_journal_issue                   31
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/b605101d
_journal_year                    2006
_chemical_formula_moiety         'C21 H27 N O, 0.5(C4 F8 I2)'
_chemical_formula_sum            'C23 H27 F4 I N O'
_chemical_formula_weight         536.36
_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                71.955(2)
_cell_angle_beta                 83.598(2)
_cell_angle_gamma                89.641(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8806(8)
_cell_length_b                   11.9639(12)
_cell_length_c                   12.6870(12)
_cell_measurement_reflns_used    7083
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.60
_cell_volume                     1129.73(19)
_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 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11532
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    1.464
_exptl_absorpt_correction_T_max  0.740
_exptl_absorpt_correction_T_min  0.642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.30; (Sheldrick)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             538
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.885
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0300
_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)+(0.0446P)²+0.3532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0776
_reflns_number_gt                5066
_reflns_number_total             5545
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b605101d.txt
_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               7101322
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 0.3948(3) 1.0286(2) 0.8734(2) 0.0288(5) Uani 1 1 d .
H1 H 0.3371 1.0223 0.9449 0.035 Uiso 1 1 calc R
C2 C 0.4295(3) 0.9263(2) 0.8478(2) 0.0269(5) Uani 1 1 d .
H2 H 0.3970 0.8522 0.9012 0.032 Uiso 1 1 calc R
C3 C 0.5131(3) 0.9321(2) 0.74252(19) 0.0228(4) Uani 1 1 d .
C4 C 0.5558(3) 1.0449(2) 0.66942(19) 0.0247(4) Uani 1 1 d .
H4 H 0.6116 1.0545 0.5967 0.030 Uiso 1 1 calc R
C5 C 0.5172(3) 1.1422(2) 0.7025(2) 0.0251(4) Uani 1 1 d .
H5 H 0.5484 1.2177 0.6513 0.030 Uiso 1 1 calc R
C6 C 0.5486(3) 0.8232(2) 0.7162(2) 0.0253(5) Uani 1 1 d .
H6 H 0.5114 0.7518 0.7724 0.030 Uiso 1 1 calc R
C7 C 0.6288(3) 0.81424(19) 0.6202(2) 0.0245(4) Uani 1 1 d .
H7 H 0.6676 0.8855 0.5645 0.029 Uiso 1 1 calc R
C8 C 0.6619(3) 0.70529(19) 0.59354(18) 0.0230(4) Uani 1 1 d .
C9 C 0.6124(3) 0.5935(2) 0.66848(19) 0.0261(5) Uani 1 1 d .
H9 H 0.5566 0.5873 0.7405 0.031 Uiso 1 1 calc R
C10 C 0.6434(3) 0.4935(2) 0.6395(2) 0.0273(5) Uani 1 1 d .
H10 H 0.6090 0.4190 0.6915 0.033 Uiso 1 1 calc R
C11 C 0.7250(3) 0.4999(2) 0.53414(19) 0.0250(5) Uani 1 1 d .
C12 C 0.7766(3) 0.6088(2) 0.45855(19) 0.0265(5) Uani 1 1 d .
H12 H 0.8329 0.6144 0.3868 0.032 Uiso 1 1 calc R
C13 C 0.7448(3) 0.7094(2) 0.48934(19) 0.0257(5) Uani 1 1 d .
H13 H 0.7808 0.7838 0.4375 0.031 Uiso 1 1 calc R
C14 C 0.8277(3) 0.3910(2) 0.40991(19) 0.0257(5) Uani 1 1 d .
H14A H 0.9449 0.4259 0.3952 0.031 Uiso 1 1 calc R
H14B H 0.7615 0.4350 0.3491 0.031 Uiso 1 1 calc R
C15 C 0.8317(3) 0.2621(2) 0.41842(19) 0.0256(5) Uani 1 1 d .
H15A H 0.7133 0.2290 0.4365 0.031 Uiso 1 1 calc R
H15B H 0.8965 0.2203 0.4809 0.031 Uiso 1 1 calc R
C16 C 0.9116(3) 0.2388(2) 0.3128(2) 0.0253(5) Uani 1 1 d .
H16A H 1.0269 0.2768 0.2909 0.030 Uiso 1 1 calc R
H16B H 0.8413 0.2739 0.2515 0.030 Uiso 1 1 calc R
C17 C 0.9255(3) 0.1072(2) 0.32987(19) 0.0252(5) Uani 1 1 d .
H17A H 0.9926 0.0725 0.3931 0.030 Uiso 1 1 calc R
H17B H 0.8094 0.0703 0.3508 0.030 Uiso 1 1 calc R
C18 C 1.0082(3) 0.0768(2) 0.22839(19) 0.0238(4) Uani 1 1 d .
H18A H 0.9432 0.1128 0.1644 0.029 Uiso 1 1 calc R
H18B H 1.1259 0.1110 0.2086 0.029 Uiso 1 1 calc R
C19 C 1.0147(3) -0.0546(2) 0.24790(19) 0.0240(4) Uani 1 1 d .
H19A H 0.8964 -0.0870 0.2593 0.029 Uiso 1 1 calc R
H19B H 1.0672 -0.0914 0.3174 0.029 Uiso 1 1 calc R
C20 C 1.1142(3) -0.0887(2) 0.1533(2) 0.0284(5) Uani 1 1 d .
H20A H 1.2300 -0.0516 0.1377 0.034 Uiso 1 1 calc R
H20B H 1.0563 -0.0582 0.0852 0.034 Uiso 1 1 calc R
C21 C 1.1296(4) -0.2217(2) 0.1807(3) 0.0387(6) Uani 1 1 d .
H21A H 1.1834 -0.2528 0.2496 0.058 Uiso 1 1 calc R
H21B H 1.1997 -0.2394 0.1193 0.058 Uiso 1 1 calc R
H21C H 1.0157 -0.2584 0.1908 0.058 Uiso 1 1 calc R
N1 N 0.4378(3) 1.13600(18) 0.80355(18) 0.0270(4) Uani 1 1 d .
O1 O 0.7469(2) 0.39418(15) 0.51603(14) 0.0289(4) Uani 1 1 d .
C22 C 0.2354(3) 0.4381(2) 0.9781(2) 0.0274(5) Uani 1 1 d .
C23 C 0.0408(3) 0.45463(18) 0.97315(17) 0.0211(4) Uani 1 1 d .
F1 F 0.3172(2) 0.54288(14) 0.92710(16) 0.0436(4) Uani 1 1 d .
F2 F 0.2655(2) 0.40393(17) 1.08584(14) 0.0444(4) Uani 1 1 d .
F3 F 0.01393(18) 0.48775(12) 0.86510(11) 0.0275(3) Uani 1 1 d .
F4 F -0.03800(18) 0.34928(11) 1.02516(11) 0.0279(3) Uani 1 1 d .
I1 I 0.330658(18) 0.310263(13) 0.899552(12) 0.02647(6) 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 123.8(2) .
N1 C1 H1 118.1 .
C2 C1 H1 118.1 .
C1 C2 C3 119.7(2) .
C1 C2 H2 120.1 .
C3 C2 H2 120.1 .
C4 C3 C2 116.1(2) .
C4 C3 C6 124.7(2) .
C2 C3 C6 119.2(2) .
C5 C4 C3 120.2(2) .
C5 C4 H4 119.9 .
C3 C4 H4 119.9 .
N1 C5 C4 123.4(2) .
N1 C5 H5 118.3 .
C4 C5 H5 118.3 .
C7 C6 C3 126.2(2) .
C7 C6 H6 116.9 .
C3 C6 H6 116.9 .
C6 C7 C8 126.1(2) .
C6 C7 H7 116.9 .
C8 C7 H7 116.9 .
C13 C8 C9 117.1(2) .
C13 C8 C7 119.9(2) .
C9 C8 C7 123.0(2) .
C10 C9 C8 121.2(2) .
C10 C9 H9 119.4 .
C8 C9 H9 119.4 .
C9 C10 C11 120.7(2) .
C9 C10 H10 119.7 .
C11 C10 H10 119.7 .
O1 C11 C12 125.8(2) .
O1 C11 C10 114.6(2) .
C12 C11 C10 119.6(2) .
C11 C12 C13 119.1(2) .
C11 C12 H12 120.5 .
C13 C12 H12 120.5 .
C12 C13 C8 122.4(2) .
C12 C13 H13 118.8 .
C8 C13 H13 118.8 .
O1 C14 C15 105.26(18) .
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 113.93(19) .
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 111.36(19) .
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 114.48(19) .
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 .
C19 C18 C17 112.71(18) .
C19 C18 H18A 109.0 .
C17 C18 H18A 109.0 .
C19 C18 H18B 109.0 .
C17 C18 H18B 109.0 .
H18A C18 H18B 107.8 .
C18 C19 C20 114.21(19) .
C18 C19 H19A 108.7 .
C20 C19 H19A 108.7 .
C18 C19 H19B 108.7 .
C20 C19 H19B 108.7 .
H19A C19 H19B 107.6 .
C19 C20 C21 112.3(2) .
C19 C20 H20A 109.1 .
C21 C20 H20A 109.1 .
C19 C20 H20B 109.1 .
C21 C20 H20B 109.1 .
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 .
C1 N1 C5 116.8(2) .
C11 O1 C14 119.11(18) .
F2 C22 F1 107.6(2) .
F2 C22 C23 108.71(19) .
F1 C22 C23 108.65(19) .
F2 C22 I1 110.03(16) .
F1 C22 I1 109.97(16) .
C23 C22 I1 111.75(15) .
F3 C23 F4 108.59(18) .
F3 C23 C22 107.57(17) .
F4 C23 C22 107.55(17) .
F3 C23 C23 108.6(2) 2_567
F4 C23 C23 108.3(2) 2_567
C22 C23 C23 116.0(2) 2_567
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.336(3) .
C1 C2 1.379(4) .
C1 H1 0.9500 .
C2 C3 1.403(3) .
C2 H2 0.9500 .
C3 C4 1.399(3) .
C3 C6 1.460(3) .
C4 C5 1.376(3) .
C4 H4 0.9500 .
C5 N1 1.343(3) .
C5 H5 0.9500 .
C6 C7 1.342(3) .
C6 H6 0.9500 .
C7 C8 1.460(3) .
C7 H7 0.9500 .
C8 C13 1.394(3) .
C8 C9 1.408(3) .
C9 C10 1.369(3) .
C9 H9 0.9500 .
C10 C11 1.397(3) .
C10 H10 0.9500 .
C11 O1 1.361(3) .
C11 C12 1.389(3) .
C12 C13 1.389(3) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 O1 1.435(3) .
C14 C15 1.513(3) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.520(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.526(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.522(3) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.515(3) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.520(3) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.527(4) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 F2 1.348(3) .
C22 F1 1.349(3) .
C22 C23 1.551(3) .
C22 I1 2.159(2) .
C23 F3 1.345(2) .
C23 F4 1.346(2) .
C23 C23 1.552(4) 2_567
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 -0.7(4) .
C1 C2 C3 C4 -0.1(3) .
C1 C2 C3 C6 -179.8(2) .
C2 C3 C4 C5 0.6(3) .
C6 C3 C4 C5 -179.7(2) .
C3 C4 C5 N1 -0.4(4) .
C4 C3 C6 C7 1.1(4) .
C2 C3 C6 C7 -179.2(2) .
C3 C6 C7 C8 -179.0(2) .
C6 C7 C8 C13 179.1(2) .
C6 C7 C8 C9 -0.4(4) .
C13 C8 C9 C10 -0.6(3) .
C7 C8 C9 C10 178.9(2) .
C8 C9 C10 C11 -0.1(4) .
C9 C10 C11 O1 -179.7(2) .
C9 C10 C11 C12 0.6(4) .
O1 C11 C12 C13 179.9(2) .
C10 C11 C12 C13 -0.4(4) .
C11 C12 C13 C8 -0.3(4) .
C9 C8 C13 C12 0.8(3) .
C7 C8 C13 C12 -178.7(2) .
O1 C14 C15 C16 179.37(18) .
C14 C15 C16 C17 175.2(2) .
C15 C16 C17 C18 -178.66(19) .
C16 C17 C18 C19 -178.34(19) .
C17 C18 C19 C20 -173.43(19) .
C18 C19 C20 C21 175.3(2) .
C2 C1 N1 C5 0.9(3) .
C4 C5 N1 C1 -0.3(3) .
C12 C11 O1 C14 -1.0(3) .
C10 C11 O1 C14 179.3(2) .
C15 C14 O1 C11 179.9(2) .
F2 C22 C23 F3 -179.52(18) .
F1 C22 C23 F3 63.6(2) .
I1 C22 C23 F3 -57.9(2) .
F2 C22 C23 F4 -62.7(2) .
F1 C22 C23 F4 -179.58(18) .
I1 C22 C23 F4 58.9(2) .
F2 C22 C23 C23 58.7(3) 2_567
F1 C22 C23 C23 -58.2(3) 2_567
I1 C22 C23 C23 -179.68(19) 2_567
