#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/07/2240788.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2240788
loop_
_publ_author_name
'Wan, Hui-Da'
'Hong, Jian-Quan'
_publ_section_title
;
 Crystal structure of
 di-μ-iodido-bis{[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]lithium}
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m137
_journal_page_last               m138
_journal_paper_doi               10.1107/S2056989015009822
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          '[Li2 (C27 H36 N2)2 I2]'
_chemical_formula_moiety         'C54 H72 I2 Li2 N4'
_chemical_formula_sum            'C54 H72 I2 Li2 N4'
_chemical_formula_weight         1044.84
_chemical_name_systematic
;
Di-μ-iodido-bis{[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]lithium}
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 105.565(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.645(4)
_cell_length_b                   14.490(6)
_cell_length_c                   19.217(7)
_cell_measurement_reflns_used    3834
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.6
_cell_measurement_theta_min      2.4
_cell_volume                     2855.4(19)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0851
_diffrn_reflns_av_sigmaI/netI    0.0803
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11711
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    1.135
_exptl_absorpt_correction_T_max  0.805
_exptl_absorpt_correction_T_min  0.727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2007)
;
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.736
_refine_diff_density_min         -1.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         5069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0537
_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)+(0.0129P)²+2.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                2924
_reflns_number_total             5069
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5851sup1.cf
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2240788
_cod_database_fobs_code          2240788
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Li Li1 0.5511(8) 0.9291(5) 0.9451(4) 0.073(2) Uani d . 1 1
N N1 0.5147(3) 0.7930(2) 0.81899(15) 0.0471(8) Uani d . 1 1
N N2 0.7164(3) 0.8253(2) 0.85073(15) 0.0495(8) Uani d . 1 1
I I1 0.45770(6) 1.10068(3) 0.918028(19) 0.1292(3) Uani d . 1 1
C C1 0.6043(4) 0.8421(3) 0.86912(18) 0.0465(9) Uani d . 1 1
C C2 0.5699(4) 0.7470(3) 0.7712(2) 0.0613(11) Uani d . 1 1
H H2 0.5272 0.7092 0.7331 0.074 Uiso calc R 1 1
C C3 0.6961(5) 0.7677(3) 0.7908(2) 0.0614(12) Uani d . 1 1
H H3 0.7589 0.7475 0.7687 0.074 Uiso calc R 1 1
C C4 0.3808(4) 0.7834(3) 0.81913(19) 0.0490(10) Uani d . 1 1
C C5 0.3503(5) 0.7218(3) 0.8690(2) 0.0620(11) Uani d . 1 1
C C6 0.2220(5) 0.7133(4) 0.8677(3) 0.0815(15) Uani d . 1 1
H H6 0.1990 0.6744 0.9008 0.098 Uiso calc R 1 1
C C7 0.1267(5) 0.7603(4) 0.8191(3) 0.0898(17) Uani d . 1 1
H H7 0.0398 0.7519 0.8185 0.108 Uiso calc R 1 1
C C8 0.1584(5) 0.8200(3) 0.7711(3) 0.0780(14) Uani d . 1 1
H H8 0.0924 0.8520 0.7385 0.094 Uiso calc R 1 1
C C9 0.2867(4) 0.8334(3) 0.7702(2) 0.0587(11) Uani d . 1 1
C C10 0.4551(5) 0.6667(4) 0.9205(3) 0.0937(17) Uani d . 1 1
H H10 0.5353 0.7035 0.9313 0.112 Uiso calc R 1 1
C C11 0.4827(7) 0.5777(5) 0.8879(4) 0.148(3) Uani d . 1 1
H H11A 0.5586 0.5493 0.9192 0.222 Uiso calc R 1 1
H H11B 0.4980 0.5896 0.8417 0.222 Uiso calc R 1 1
H H11C 0.4093 0.5371 0.8820 0.222 Uiso calc R 1 1
C C12 0.4245(8) 0.6461(5) 0.9924(3) 0.153(3) Uani d . 1 1
H H12A 0.5024 0.6257 1.0271 0.229 Uiso calc R 1 1
H H12B 0.3594 0.5987 0.9854 0.229 Uiso calc R 1 1
H H12C 0.3927 0.7010 1.0098 0.229 Uiso calc R 1 1
C C13 0.3189(5) 0.9005(3) 0.7174(2) 0.0703(13) Uani d . 1 1
H H13 0.4135 0.9100 0.7314 0.084 Uiso calc R 1 1
C C14 0.2809(7) 0.8614(5) 0.6418(3) 0.127(2) Uani d . 1 1
H H14A 0.2993 0.9059 0.6089 0.190 Uiso calc R 1 1
H H14B 0.1894 0.8474 0.6282 0.190 Uiso calc R 1 1
H H14C 0.3298 0.8061 0.6404 0.190 Uiso calc R 1 1
C C15 0.2544(6) 0.9935(4) 0.7182(3) 0.112(2) Uani d . 1 1
H H15A 0.2695 1.0144 0.7671 0.168 Uiso calc R 1 1
H H15B 0.1623 0.9878 0.6966 0.168 Uiso calc R 1 1
H H15C 0.2904 1.0372 0.6912 0.168 Uiso calc R 1 1
C C16 0.8436(4) 0.8581(3) 0.8895(2) 0.0534(10) Uani d . 1 1
C C17 0.8907(4) 0.9376(3) 0.8648(2) 0.0611(11) Uani d . 1 1
C C18 1.0158(5) 0.9638(3) 0.9004(3) 0.0814(14) Uani d . 1 1
H H18 1.0511 1.0160 0.8847 0.098 Uiso calc R 1 1
C C19 1.0898(5) 0.9153(4) 0.9582(3) 0.0869(16) Uani d . 1 1
H H19 1.1738 0.9348 0.9816 0.104 Uiso calc R 1 1
C C20 1.0385(5) 0.8372(4) 0.9814(3) 0.0823(15) Uani d . 1 1
H H20 1.0892 0.8043 1.0205 0.099 Uiso calc R 1 1
C C21 0.9143(4) 0.8066(3) 0.9482(2) 0.0645(12) Uani d . 1 1
C C22 0.8123(5) 0.9924(3) 0.8010(2) 0.0720(13) Uani d . 1 1
H H22 0.7264 0.9631 0.7854 0.086 Uiso calc R 1 1
C C23 0.8713(6) 0.9880(5) 0.7376(3) 0.135(3) Uani d . 1 1
H H23A 0.8821 0.9247 0.7258 0.202 Uiso calc R 1 1
H H23B 0.9546 1.0182 0.7502 0.202 Uiso calc R 1 1
H H23C 0.8144 1.0183 0.6967 0.202 Uiso calc R 1 1
C C24 0.7897(6) 1.0907(3) 0.8207(3) 0.1030(18) Uani d . 1 1
H H24A 0.8717 1.1226 0.8353 0.155 Uiso calc R 1 1
H H24B 0.7493 1.0909 0.8598 0.155 Uiso calc R 1 1
H H24C 0.7338 1.1212 0.7796 0.155 Uiso calc R 1 1
C C25 0.8619(5) 0.7196(4) 0.9735(3) 0.0839(15) Uani d . 1 1
H H25 0.7715 0.7119 0.9446 0.101 Uiso calc R 1 1
C C26 0.9377(6) 0.6344(4) 0.9617(3) 0.112(2) Uani d . 1 1
H H26A 1.0273 0.6404 0.9888 0.168 Uiso calc R 1 1
H H26B 0.9329 0.6286 0.9113 0.168 Uiso calc R 1 1
H H26C 0.9008 0.5804 0.9775 0.168 Uiso calc R 1 1
C C27 0.8602(6) 0.7278(5) 1.0525(3) 0.134(3) Uani d . 1 1
H H27A 0.8199 0.6740 1.0662 0.200 Uiso calc R 1 1
H H27B 0.8117 0.7817 1.0585 0.200 Uiso calc R 1 1
H H27C 0.9480 0.7329 1.0825 0.200 Uiso calc R 1 1
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'
Li Li -0.0003 0.0001 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C1 Li1 I1 . . 124.9(3)
C1 Li1 I1 . 3_677 131.6(4)
I1 Li1 I1 . 3_677 103.4(2)
C1 Li1 Li1 . 3_677 175.8(5)
I1 Li1 Li1 . 3_677 51.9(2)
I1 Li1 Li1 3_677 3_677 51.48(18)
C1 N1 C2 . . 112.3(3)
C1 N1 C4 . . 123.9(3)
C2 N1 C4 . . 123.6(3)
C1 N2 C3 . . 111.8(3)
C1 N2 C16 . . 125.3(3)
C3 N2 C16 . . 122.8(3)
Li1 I1 Li1 . 3_677 76.6(2)
N2 C1 N1 . . 102.8(3)
N2 C1 Li1 . . 134.7(4)
N1 C1 Li1 . . 122.2(3)
C3 C2 N1 . . 106.2(4)
C3 C2 H2 . . 126.9
N1 C2 H2 . . 126.9
C2 C3 N2 . . 106.9(4)
C2 C3 H3 . . 126.5
N2 C3 H3 . . 126.5
C9 C4 C5 . . 122.5(4)
C9 C4 N1 . . 119.2(3)
C5 C4 N1 . . 118.3(4)
C6 C5 C4 . . 117.2(4)
C6 C5 C10 . . 121.7(4)
C4 C5 C10 . . 121.1(4)
C7 C6 C5 . . 121.6(5)
C7 C6 H6 . . 119.2
C5 C6 H6 . . 119.2
C6 C7 C8 . . 120.3(5)
C6 C7 H7 . . 119.8
C8 C7 H7 . . 119.8
C7 C8 C9 . . 121.3(5)
C7 C8 H8 . . 119.4
C9 C8 H8 . . 119.4
C4 C9 C8 . . 117.1(4)
C4 C9 C13 . . 122.8(4)
C8 C9 C13 . . 120.1(4)
C11 C10 C5 . . 112.0(5)
C11 C10 C12 . . 108.8(5)
C5 C10 C12 . . 113.4(5)
C11 C10 H10 . . 107.4
C5 C10 H10 . . 107.4
C12 C10 H10 . . 107.4
C10 C11 H11A . . 109.5
C10 C11 H11B . . 109.5
H11A C11 H11B . . 109.5
C10 C11 H11C . . 109.5
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
C10 C12 H12A . . 109.5
C10 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
C10 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
C14 C13 C9 . . 110.7(4)
C14 C13 C15 . . 109.8(4)
C9 C13 C15 . . 112.4(4)
C14 C13 H13 . . 107.9
C9 C13 H13 . . 107.9
C15 C13 H13 . . 107.9
C13 C14 H14A . . 109.5
C13 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
C13 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
C13 C15 H15A . . 109.5
C13 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
C13 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
C17 C16 C21 . . 123.7(4)
C17 C16 N2 . . 118.2(4)
C21 C16 N2 . . 118.1(4)
C18 C17 C16 . . 116.6(4)
C18 C17 C22 . . 120.5(4)
C16 C17 C22 . . 122.8(4)
C19 C18 C17 . . 122.0(5)
C19 C18 H18 . . 119.0
C17 C18 H18 . . 119.0
C18 C19 C20 . . 119.4(5)
C18 C19 H19 . . 120.3
C20 C19 H19 . . 120.3
C21 C20 C19 . . 121.8(5)
C21 C20 H20 . . 119.1
C19 C20 H20 . . 119.1
C20 C21 C16 . . 116.5(5)
C20 C21 C25 . . 120.7(4)
C16 C21 C25 . . 122.8(4)
C24 C22 C17 . . 112.6(4)
C24 C22 C23 . . 111.7(5)
C17 C22 C23 . . 111.9(4)
C24 C22 H22 . . 106.7
C17 C22 H22 . . 106.7
C23 C22 H22 . . 106.7
C22 C23 H23A . . 109.5
C22 C23 H23B . . 109.5
H23A C23 H23B . . 109.5
C22 C23 H23C . . 109.5
H23A C23 H23C . . 109.5
H23B C23 H23C . . 109.5
C22 C24 H24A . . 109.5
C22 C24 H24B . . 109.5
H24A C24 H24B . . 109.5
C22 C24 H24C . . 109.5
H24A C24 H24C . . 109.5
H24B C24 H24C . . 109.5
C21 C25 C26 . . 111.8(4)
C21 C25 C27 . . 111.0(5)
C26 C25 C27 . . 111.1(5)
C21 C25 H25 . . 107.6
C26 C25 H25 . . 107.6
C27 C25 H25 . . 107.6
C25 C26 H26A . . 109.5
C25 C26 H26B . . 109.5
H26A C26 H26B . . 109.5
C25 C26 H26C . . 109.5
H26A C26 H26C . . 109.5
H26B C26 H26C . . 109.5
C25 C27 H27A . . 109.5
C25 C27 H27B . . 109.5
H27A C27 H27B . . 109.5
C25 C27 H27C . . 109.5
H27A C27 H27C . . 109.5
H27B C27 H27C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Li1 C1 . 2.120(7) y
Li1 I1 . 2.676(8) y
Li1 I1 3_677 2.691(7) y
Li1 Li1 3_677 3.328(13) ?
N1 C1 . 1.360(4) ?
N1 C2 . 1.386(5) ?
N1 C4 . 1.433(5) ?
N2 C1 . 1.354(4) ?
N2 C3 . 1.391(5) ?
N2 C16 . 1.440(5) ?
I1 Li1 3_677 2.691(7) ?
C2 C3 . 1.328(5) ?
C2 H2 . 0.9300 ?
C3 H3 . 0.9300 ?
C4 C9 . 1.382(5) ?
C4 C5 . 1.410(5) ?
C5 C6 . 1.365(6) ?
C5 C10 . 1.507(6) ?
C6 C7 . 1.363(6) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.371(7) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.384(6) ?
C8 H8 . 0.9300 ?
C9 C13 . 1.510(6) ?
C10 C11 . 1.497(8) ?
C10 C12 . 1.531(7) ?
C10 H10 . 0.9800 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C14 . 1.509(7) ?
C13 C15 . 1.514(7) ?
C13 H13 . 0.9800 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 C17 . 1.389(6) ?
C16 C21 . 1.393(6) ?
C17 C18 . 1.377(6) ?
C17 C22 . 1.510(6) ?
C18 C19 . 1.371(6) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.382(7) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.378(6) ?
C20 H20 . 0.9300 ?
C21 C25 . 1.512(6) ?
C22 C24 . 1.509(6) ?
C22 C23 . 1.514(7) ?
C22 H22 . 0.9800 ?
C23 H23A . 0.9600 ?
C23 H23B . 0.9600 ?
C23 H23C . 0.9600 ?
C24 H24A . 0.9600 ?
C24 H24B . 0.9600 ?
C24 H24C . 0.9600 ?
C25 C26 . 1.525(7) ?
C25 C27 . 1.527(7) ?
C25 H25 . 0.9800 ?
C26 H26A . 0.9600 ?
C26 H26B . 0.9600 ?
C26 H26C . 0.9600 ?
C27 H27A . 0.9600 ?
C27 H27B . 0.9600 ?
C27 H27C . 0.9600 ?
