#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:14:26 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178806 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/60/4106040.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_4106040
loop_
_publ_author_name
'Cyprien Lemouchi'
'Cortnie S. Vogelsberg'
'Leokadiya Zorina'
'Sergey Simonov'
'Patrick Batail'
'Stuart E. Brown'
'Miguel A. Garcia-Garibay'
_publ_contact_author_address
;
Laboratoire de Chimie et Ingénierie Moléculaire d'Angers,
CNRS-Université d'Angers, 49045 Angers, France
;
_publ_contact_author_email       patrick.batail@univ-angers.fr
_publ_contact_author_name        'Dr. Patrick Batail'
_publ_section_title
;
 Ultra-fast Rotors for Molecular Machines and Functional Materials via
 Halogen Bonding: Crystals of 1,4-Bis(iodoethynyl)bicyclo[2.2.2]octane
 with Distinct Gigahertz Rotation at Two Sites
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6371
_journal_page_last               6379
_journal_paper_doi               10.1021/ja200503j
_journal_volume                  133
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C12 H12 I2'
_chemical_formula_sum            'C12 H12 I2'
_chemical_formula_weight         410.02
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-97 and WinGX routine-INITIALISE'
_cell_angle_alpha                90.00
_cell_angle_beta                 111.674(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.576(2)
_cell_length_b                   7.1977(5)
_cell_length_c                   12.2949(7)
_cell_measurement_reflns_used    7919
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      5
_cell_volume                     2596.8(3)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'DIAMOND 3.1 (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker KappaCCD'
_diffrn_measurement_method       'combined φ/ω-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  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29119
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         4.17
_exptl_absorpt_coefficient_mu    4.808
_exptl_absorpt_correction_T_max  0.648
_exptl_absorpt_correction_T_min  0.212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS of Bruker KappaCCD'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.098
_exptl_crystal_description       plate
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.604
_refine_diff_density_min         -1.035
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0364
_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)+(0.0522P)²+8.7384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                2901
_reflns_number_total             3954
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja200503j_si_004.cif
_cod_data_source_block           cl178-RT-final
_cod_original_cell_volume        2596.7(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4106040
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'
'-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 0.123438(11) 0.20192(5) 1.24832(2) 0.06130(12) Uani 1 1 d .
C1 C 0.08227(17) 0.2338(7) 1.0821(4) 0.0583(10) Uani 1 1 d .
C2 C 0.05720(16) 0.2438(8) 0.9828(4) 0.0583(10) Uani 1 1 d .
C3 C 0.02684(14) 0.2478(7) 0.8595(4) 0.0524(9) Uani 1 1 d .
C4 C -0.0160(3) 0.3454(16) 0.8428(5) 0.135(4) Uani 1 1 d .
H4A H -0.0098 0.4765 0.8595 0.162 Uiso 1 1 calc R
H4B H -0.0290 0.2967 0.8972 0.162 Uiso 1 1 calc R
C5 C 0.0135(3) 0.0431(10) 0.8164(6) 0.102(2) Uani 1 1 d .
H5A H 0.0408 -0.0317 0.8343 0.123 Uiso 1 1 calc R
H5B H -0.0050 -0.0105 0.8564 0.123 Uiso 1 1 calc R
C6 C 0.0506(2) 0.3218(13) 0.7837(5) 0.107(3) Uani 1 1 d .
H6A H 0.0745 0.2368 0.7844 0.128 Uiso 1 1 calc R
H6B H 0.0645 0.4408 0.8137 0.128 Uiso 1 1 calc R
I2 I 0.128679(12) 1.32878(5) 0.57020(3) 0.06742(12) Uani 1 1 d .
C11 C 0.16939(16) 1.1364(7) 0.5453(4) 0.0562(10) Uani 1 1 d .
C12 C 0.19359(15) 1.0240(7) 0.5294(4) 0.0561(10) Uani 1 1 d .
C13 C 0.22352(14) 0.8786(6) 0.5134(4) 0.0512(9) Uani 1 1 d .
C7A C 0.2643(6) 0.9533(16) 0.501(2) 0.116(8) Uani 0.50 1 d P
H7A1 H 0.2798 1.0347 0.5667 0.139 Uiso 0.50 1 calc PR
H7A2 H 0.2558 1.0259 0.4299 0.139 Uiso 0.50 1 calc PR
C8A C 0.2386(6) 0.743(2) 0.6229(11) 0.084(4) Uani 0.50 1 d P
H8A1 H 0.2565 0.8120 0.6927 0.100 Uiso 0.50 1 calc PR
H8A2 H 0.2118 0.6952 0.6339 0.100 Uiso 0.50 1 calc PR
C9A C 0.1986(6) 0.758(3) 0.4106(14) 0.107(7) Uani 0.50 1 d P
H9A1 H 0.1876 0.8328 0.3400 0.128 Uiso 0.50 1 calc PR
H9A2 H 0.1724 0.7019 0.4212 0.128 Uiso 0.50 1 calc PR
C7B C 0.2670(6) 0.581(2) 0.6057(12) 0.091(4) Uani 0.50 1 d P
H7B1 H 0.2505 0.4655 0.5989 0.109 Uiso 0.50 1 calc PR
H7B2 H 0.2956 0.5724 0.6721 0.109 Uiso 0.50 1 calc PR
C8B C 0.2968(8) 0.794(2) 0.497(4) 0.167(15) Uani 0.50 1 d P
H8B1 H 0.3063 0.8135 0.4316 0.200 Uiso 0.50 1 calc PR
H8B2 H 0.3239 0.7966 0.5683 0.200 Uiso 0.50 1 calc PR
C9B C 0.2301(5) 0.605(3) 0.3972(14) 0.110(7) Uani 0.50 1 d P
H9B1 H 0.2176 0.4842 0.4042 0.132 Uiso 0.50 1 calc PR
H9B2 H 0.2316 0.6127 0.3200 0.132 Uiso 0.50 1 calc PR
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'
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_1
_geom_angle_site_symmetry_3
C2 C1 I1 176.8(5) . .
C1 C2 C3 177.5(6) . .
C2 C3 C4 111.8(4) . .
C2 C3 C6 111.4(4) . .
C4 C3 C6 113.0(6) . .
C2 C3 C5 108.8(4) . .
C4 C3 C5 106.4(6) . .
C6 C3 C5 105.0(5) . .
C3 C4 C6 111.2(5) . 2_556
C5 C5 C3 109.5(3) 2_556 .
C3 C6 C4 109.6(5) . 2_556
C12 C11 I2 179.1(4) . .
C11 C12 C13 177.5(5) . .
C8B C13 C12 110.6(7) 7_566 .
C7A C13 C12 112.8(6) . .
C8B C13 C9B 116.3(17) 7_566 7_566
C12 C13 C9B 110.7(6) . 7_566
C7A C13 C9A 109.7(13) . .
C12 C13 C9A 111.2(6) . .
C7A C13 C8A 108.3(12) . .
C12 C13 C8A 109.3(5) . .
C9A C13 C8A 105.1(11) . .
C8B C13 C7B 107.9(16) 7_566 7_566
C12 C13 C7B 109.6(5) . 7_566
C9B C13 C7B 101.2(12) 7_566 7_566
C13 C7A C8B 110.6(9) . .
C7B C8A C13 111.0(8) . .
C13 C9A C9B 110.3(9) . .
C8A C7B C13 107.6(8) . 7_566
C13 C8B C7A 112.2(11) 7_566 .
C13 C9B C9A 111.5(9) 7_566 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C1 1.989(5) .
C1 C2 1.187(6) .
C2 C3 1.464(6) .
C3 C4 1.469(7) .
C3 C6 1.495(7) .
C3 C5 1.570(9) .
C4 C6 1.545(8) 2_556
C5 C5 1.537(13) 2_556
C6 C4 1.545(8) 2_556
I2 C11 1.989(5) .
C11 C12 1.178(6) .
C12 C13 1.471(6) .
C13 C8B 1.381(16) 7_566
C13 C7A 1.452(13) .
C13 C9B 1.475(12) 7_566
C13 C9A 1.497(13) .
C13 C8A 1.586(12) .
C13 C7B 1.626(13) 7_566
C7A C8B 1.55(2) .
C8A C7B 1.530(16) .
C9A C9B 1.535(17) .
C7B C13 1.626(13) 7_566
C8B C13 1.381(16) 7_566
C9B C13 1.475(12) 7_566
