#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:22:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180426 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/95/7209553.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_7209553
loop_
_publ_author_name
'Walter, Sebastian M.'
'Sarwar, Mohammed G.'
'Chudzinski, Michael G.'
'Herdtweck, Eberhardt'
'Lough, Alan J.'
'Huber, Stefan M.'
'Taylor, Mark S.'
_publ_section_title
;
 Halogen bonding and π--π interactions in the solid-state structure of a
 butadiynylene-linked bis(iodoperfluoroarene)
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              3097
_journal_paper_doi               10.1039/c2ce26751a
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C16 H36 N, C16 F8 I2, I'
_chemical_formula_sum            'C32 H36 F8 I3 N'
_chemical_formula_weight         967.32
_chemical_name_systematic
;
?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.2920(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7911(4)
_cell_length_b                   30.7832(10)
_cell_length_c                   8.3658(1)
_cell_measurement_reflns_used    12445
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     3530.17(16)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12445
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.65
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.721
_exptl_absorpt_correction_T_max  0.768
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1864
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.131
_refine_diff_density_min         -1.462
_refine_diff_density_rms         0.138
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.51(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6063
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0433
_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)+(0.0413P)²+27.6591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1060
_reflns_number_gt                5333
_reflns_number_total             6063
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2ce26751a.txt
_cod_data_source_block           k09110
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7209553
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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
I1 I 0.07691(4) -0.10960(2) 0.55609(6) 0.03673(17) Uani 1 1 d .
I2 I 0.36690(4) 0.117863(19) 0.13435(6) 0.03530(17) Uani 1 1 d .
I3 I 0.21408(6) 0.208121(17) 0.10738(8) 0.03324(14) Uani 1 1 d .
F1 F -0.1219(5) -0.0922(2) 0.6942(8) 0.0513(16) Uani 1 1 d .
F2 F -0.2226(5) -0.0204(2) 0.7489(9) 0.0630(19) Uani 1 1 d .
F3 F -0.1579(6) 0.0590(2) 0.6567(9) 0.071(2) Uani 1 1 d .
F4 F 0.0040(5) 0.06442(19) 0.5074(9) 0.0596(18) Uani 1 1 d .
F5 F 0.5635(5) 0.10588(19) -0.0225(8) 0.0491(16) Uani 1 1 d .
F6 F 0.6754(5) 0.0382(2) -0.0688(9) 0.0597(18) Uani 1 1 d .
F7 F 0.6292(6) -0.0423(2) 0.0334(9) 0.068(2) Uani 1 1 d .
F8 F 0.4679(5) -0.05308(18) 0.1873(8) 0.0538(17) Uani 1 1 d .
C1 C 0.1171(8) -0.0063(3) 0.4470(13) 0.038(2) Uani 1 1 d .
C2 C 0.1898(8) 0.0000(3) 0.3836(12) 0.034(2) Uani 1 1 d .
C3 C 0.2738(8) 0.0073(3) 0.3111(13) 0.038(2) Uani 1 1 d .
C4 C 0.3445(8) 0.0144(3) 0.2483(12) 0.034(2) Uani 1 1 d .
C5 C 0.0295(8) -0.0118(3) 0.5219(12) 0.035(2) Uani 1 1 d .
C6 C -0.0049(7) -0.0524(3) 0.5717(12) 0.031(2) Uani 1 1 d .
C7 C -0.0873(8) -0.0540(3) 0.6447(13) 0.041(2) Uani 1 1 d .
C8 C -0.1410(8) -0.0170(4) 0.6745(14) 0.048(3) Uani 1 1 d .
C9 C -0.1107(10) 0.0228(4) 0.6275(15) 0.053(3) Uani 1 1 d .
C10 C -0.0270(8) 0.0249(3) 0.5515(13) 0.043(3) Uani 1 1 d .
C11 C 0.4292(8) 0.0219(3) 0.1700(11) 0.033(2) Uani 1 1 d .
C12 C 0.4551(8) 0.0627(3) 0.1110(13) 0.035(2) Uani 1 1 d .
C13 C 0.5375(7) 0.0674(3) 0.0330(12) 0.036(2) Uani 1 1 d .
C14 C 0.5946(8) 0.0324(3) 0.0082(13) 0.044(3) Uani 1 1 d .
C15 C 0.5714(9) -0.0080(4) 0.0580(15) 0.043(3) Uani 1 1 d .
C16 C 0.4905(8) -0.0130(3) 0.1380(12) 0.040(3) Uani 1 1 d .
N1 N 0.0397(5) 0.2317(2) 0.5993(8) 0.0286(16) Uani 1 1 d .
C17 C -0.0300(7) 0.2577(3) 0.4840(11) 0.036(2) Uani 1 1 d .
H17A H -0.0579 0.2813 0.5454 0.044 Uiso 1 1 calc R
H17B H -0.0845 0.2385 0.4422 0.044 Uiso 1 1 calc R
C18 C 0.0128(8) 0.2780(3) 0.3413(12) 0.043(2) Uani 1 1 d .
H18A H 0.0481 0.2557 0.2852 0.052 Uiso 1 1 calc R
H18B H 0.0597 0.3011 0.3792 0.052 Uiso 1 1 calc R
C19 C -0.0700(10) 0.2972(4) 0.2257(15) 0.066(4) Uani 1 1 d .
H19A H -0.1129 0.2735 0.1805 0.079 Uiso 1 1 calc R
H19B H -0.1096 0.3169 0.2861 0.079 Uiso 1 1 calc R
C20 C -0.0336(12) 0.3214(6) 0.0938(18) 0.095(6) Uani 1 1 d .
H20A H -0.0885 0.3348 0.0274 0.142 Uiso 1 1 calc R
H20B H 0.0007 0.3015 0.0278 0.142 Uiso 1 1 calc R
H20C H 0.0115 0.3441 0.1381 0.142 Uiso 1 1 calc R
C21 C -0.0115(6) 0.2202(3) 0.7446(11) 0.035(2) Uani 1 1 d .
H21A H -0.0358 0.2474 0.7894 0.042 Uiso 1 1 calc R
H21B H 0.0372 0.2075 0.8274 0.042 Uiso 1 1 calc R
C22 C -0.0967(8) 0.1886(3) 0.7147(12) 0.041(2) Uani 1 1 d .
H22A H -0.1422 0.1986 0.6224 0.049 Uiso 1 1 calc R
H22B H -0.0723 0.1594 0.6885 0.049 Uiso 1 1 calc R
C23 C -0.1497(7) 0.1859(4) 0.8652(13) 0.045(3) Uani 1 1 d .
H23A H -0.1027 0.1776 0.9581 0.054 Uiso 1 1 calc R
H23B H -0.1763 0.2149 0.8877 0.054 Uiso 1 1 calc R
C24 C -0.2322(10) 0.1531(5) 0.8458(17) 0.070(4) Uani 1 1 d .
H24A H -0.2689 0.1545 0.9396 0.105 Uiso 1 1 calc R
H24B H -0.2052 0.1239 0.8369 0.105 Uiso 1 1 calc R
H24C H -0.2758 0.1598 0.7484 0.105 Uiso 1 1 calc R
C25 C 0.1302(6) 0.2590(3) 0.6573(11) 0.033(2) Uani 1 1 d .
H25A H 0.1708 0.2420 0.7399 0.039 Uiso 1 1 calc R
H25B H 0.1688 0.2630 0.5653 0.039 Uiso 1 1 calc R
C26 C 0.1130(8) 0.3033(3) 0.7269(13) 0.046(2) Uani 1 1 d .
H26A H 0.0838 0.3227 0.6402 0.055 Uiso 1 1 calc R
H26B H 0.0660 0.3006 0.8078 0.055 Uiso 1 1 calc R
C27 C 0.2056(9) 0.3232(3) 0.8044(13) 0.049(3) Uani 1 1 d .
H27A H 0.2533 0.3244 0.7243 0.059 Uiso 1 1 calc R
H27B H 0.2331 0.3041 0.8933 0.059 Uiso 1 1 calc R
C28 C 0.1929(11) 0.3686(4) 0.8707(15) 0.063(4) Uani 1 1 d .
H28A H 0.2549 0.3785 0.9274 0.095 Uiso 1 1 calc R
H28B H 0.1430 0.3681 0.9455 0.095 Uiso 1 1 calc R
H28C H 0.1727 0.3885 0.7818 0.095 Uiso 1 1 calc R
C29 C 0.0748(7) 0.1917(3) 0.5186(10) 0.032(2) Uani 1 1 d .
H29A H 0.1123 0.2013 0.4305 0.039 Uiso 1 1 calc R
H29B H 0.0169 0.1757 0.4688 0.039 Uiso 1 1 calc R
C30 C 0.1376(8) 0.1604(3) 0.6246(12) 0.042(2) Uani 1 1 d .
H30A H 0.1856 0.1769 0.6975 0.050 Uiso 1 1 calc R
H30B H 0.0960 0.1435 0.6914 0.050 Uiso 1 1 calc R
C31 C 0.1907(8) 0.1297(3) 0.5243(11) 0.038(2) Uani 1 1 d .
H31A H 0.2338 0.1465 0.4602 0.045 Uiso 1 1 calc R
H31B H 0.1427 0.1140 0.4486 0.045 Uiso 1 1 calc R
C32 C 0.2516(8) 0.0969(3) 0.6281(13) 0.046(3) Uani 1 1 d .
H32A H 0.2907 0.0796 0.5604 0.070 Uiso 1 1 calc R
H32B H 0.2084 0.0776 0.6809 0.070 Uiso 1 1 calc R
H32C H 0.2950 0.1123 0.7099 0.070 Uiso 1 1 calc R
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'
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'
N N 0.0061 0.0033 '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
C6 I1 I3 169.5(3) 2
C12 I2 I3 171.0(3) .
C2 C1 C5 177.5(11) .
C1 C2 C3 179.7(13) .
C4 C3 C2 178.5(11) .
C3 C4 C11 178.4(12) .
C10 C5 C6 116.6(10) .
C10 C5 C1 119.4(9) .
C6 C5 C1 124.0(9) .
C7 C6 C5 119.4(9) .
C7 C6 I1 118.8(7) .
C5 C6 I1 121.5(7) .
C6 C7 F1 121.0(9) .
C6 C7 C8 122.8(10) .
F1 C7 C8 116.2(9) .
F2 C8 C9 120.1(10) .
F2 C8 C7 120.4(10) .
C9 C8 C7 119.6(10) .
F3 C9 C8 121.9(12) .
F3 C9 C10 119.7(11) .
C8 C9 C10 118.4(11) .
F4 C10 C9 118.3(10) .
F4 C10 C5 118.4(10) .
C9 C10 C5 123.3(10) .
C12 C11 C16 115.6(9) .
C12 C11 C4 124.0(9) .
C16 C11 C4 120.3(9) .
C13 C12 C11 121.0(9) .
C13 C12 I2 118.1(7) .
C11 C12 I2 120.9(7) .
F5 C13 C14 117.8(9) .
F5 C13 C12 121.7(9) .
C14 C13 C12 120.5(9) .
F6 C14 C15 119.8(9) .
F6 C14 C13 119.1(9) .
C15 C14 C13 121.1(10) .
F7 C15 C14 120.3(10) .
F7 C15 C16 120.8(10) .
C14 C15 C16 118.8(9) .
F8 C16 C15 118.6(9) .
F8 C16 C11 118.3(9) .
C15 C16 C11 123.0(9) .
C29 N1 C21 111.7(7) .
C29 N1 C17 111.1(7) .
C21 N1 C17 108.4(6) .
C29 N1 C25 107.4(7) .
C21 N1 C25 107.9(7) .
C17 N1 C25 110.3(7) .
N1 C17 C18 116.2(8) .
C17 C18 C19 109.1(9) .
C20 C19 C18 112.2(12) .
N1 C21 C22 115.9(8) .
C23 C22 C21 109.2(8) .
C24 C23 C22 111.6(10) .
C26 C25 N1 117.3(8) .
C27 C26 C25 111.8(9) .
C26 C27 C28 113.9(11) .
N1 C29 C30 116.6(7) .
C31 C30 C29 110.8(8) .
C30 C31 C32 111.7(8) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C6 2.104(9) .
I1 I3 3.5752(9) 2
I2 C12 2.112(10) .
I2 I3 3.4797(8) .
F1 C7 1.352(12) .
F2 C8 1.348(12) .
F3 C9 1.327(14) .
F4 C10 1.353(12) .
F5 C13 1.334(11) .
F6 C14 1.358(12) .
F7 C15 1.350(12) .
F8 C16 1.348(11) .
C1 C2 1.200(14) .
C1 C5 1.431(15) .
C2 C3 1.383(14) .
C3 C4 1.178(14) .
C4 C11 1.420(14) .
C5 C10 1.409(15) .
C5 C6 1.415(14) .
C6 C7 1.349(13) .
C7 C8 1.396(15) .
C8 C9 1.365(16) .
C9 C10 1.379(17) .
C11 C12 1.409(13) .
C11 C16 1.410(14) .
C12 C13 1.379(13) .
C13 C14 1.364(14) .
C14 C15 1.363(15) .
C15 C16 1.371(15) .
N1 C29 1.508(11) .
N1 C21 1.513(11) .
N1 C17 1.515(12) .
N1 C25 1.539(12) .
C17 C18 1.523(13) .
C18 C19 1.533(15) .
C19 C20 1.465(18) .
C21 C22 1.526(14) .
C22 C23 1.526(13) .
C23 C24 1.516(16) .
C25 C26 1.512(13) .
C26 C27 1.498(15) .
C27 C28 1.523(15) .
C29 C30 1.517(12) .
C30 C31 1.505(13) .
C31 C32 1.523(12) .
