#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/35/2203511.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_2203511
loop_
_publ_author_name
'Liu Qing-Xiang'
'Song Hai-bin'
'Xu Feng-bo'
'Li Qing-shan'
'Zhang Zheng-zhi'
_publ_section_title
;
 The photodimer of 1-(anthracen-9-ylmethyl)-3-ethylimidazolium iodide
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o674
_journal_page_last               o675
_journal_paper_doi               10.1107/S1600536804006749
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C40 H38 N4 2+, 2I 1-'
_chemical_formula_moiety         'C40 H38 N4 2+, 2I 1-'
_chemical_formula_sum            'C40 H38 I2 N4'
_chemical_formula_weight         828.54
_chemical_melting_point          239
_chemical_name_systematic
;
9,10'-bis(3-ethylimidazolium-1-ylmethyl)-9,9':10,10'-bianthracenyl diiodide
;
_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                 106.404(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.696(5)
_cell_length_b                   21.230(13)
_cell_length_c                   11.005(7)
_cell_measurement_reflns_used    937
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.59
_cell_measurement_theta_min      2.72
_cell_volume                     1724.9(19)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7030
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.858
_exptl_absorpt_correction_T_max  0.640
_exptl_absorpt_correction_T_min  0.449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.632
_refine_ls_extinction_coef       0.0041(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0310
_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)+(0.0239P)²+1.4667P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0688
_reflns_number_gt                2215
_reflns_number_total             2903
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6216.cif
_cod_data_source_block           2
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1724.9(18)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2203511
_cod_database_fobs_code          2203511
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_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_type_symbol
I1 0.19024(4) 0.703244(12) 0.67467(3) 0.05330(14) Uani d . 1 I
N1 0.8122(4) 0.68851(12) -0.0423(3) 0.0300(7) Uani d . 1 N
N2 0.6479(4) 0.77288(14) -0.0668(3) 0.0412(8) Uani d . 1 N
C1 0.7797(5) 0.74436(16) -0.0998(3) 0.0372(9) Uani d . 1 C
H1 0.8408 0.7607 -0.1546 0.045 Uiso calc R 1 H
C2 0.5920(5) 0.73450(18) 0.0150(4) 0.0458(10) Uani d . 1 C
H2 0.5005 0.7430 0.0527 0.055 Uiso calc R 1 H
C3 0.6955(5) 0.68192(17) 0.0306(4) 0.0396(9) Uani d . 1 C
H3 0.6886 0.6476 0.0815 0.048 Uiso calc R 1 H
C4 0.9538(4) 0.64597(14) -0.0615(3) 0.0290(8) Uani d . 1 C
H4A 1.0708 0.6631 -0.0157 0.035 Uiso calc R 1 H
H4B 0.9474 0.6464 -0.1508 0.035 Uiso calc R 1 H
C5 0.9460(4) 0.57688(14) -0.0204(3) 0.0243(7) Uani d . 1 C
C6 0.9882(4) 0.56855(14) 0.1231(3) 0.0239(7) Uani d . 1 C
C7 1.0525(4) 0.61633(16) 0.2108(3) 0.0309(8) Uani d . 1 C
H7 1.0681 0.6567 0.1830 0.037 Uiso calc R 1 H
C8 1.0935(5) 0.60379(18) 0.3401(3) 0.0410(9) Uani d . 1 C
H8 1.1330 0.6362 0.3981 0.049 Uiso calc R 1 H
C9 1.0762(5) 0.54394(18) 0.3827(3) 0.0415(10) Uani d . 1 C
H9 1.1076 0.5357 0.4692 0.050 Uiso calc R 1 H
C10 1.0118(4) 0.49598(17) 0.2963(3) 0.0318(8) Uani d . 1 C
H10 0.9980 0.4556 0.3250 0.038 Uiso calc R 1 H
C11 0.9678(4) 0.50803(14) 0.1670(3) 0.0244(7) Uani d . 1 C
C12 0.8949(4) 0.45659(13) 0.0698(3) 0.0233(7) Uani d . 1 C
H12 0.8413 0.4240 0.1111 0.028 Uiso calc R 1 H
C13 0.7457(4) 0.48310(14) -0.0375(3) 0.0236(7) Uani d . 1 C
C14 0.5916(4) 0.44857(15) -0.0941(3) 0.0298(8) Uani d . 1 C
H14 0.5794 0.4081 -0.0654 0.036 Uiso calc R 1 H
C15 0.4562(4) 0.47330(16) -0.1923(3) 0.0348(9) Uani d . 1 C
H15 0.3531 0.4497 -0.2295 0.042 Uiso calc R 1 H
C16 0.4743(5) 0.53343(17) -0.2354(3) 0.0363(9) Uani d . 1 C
H16 0.3826 0.5504 -0.3014 0.044 Uiso calc R 1 H
C17 0.6282(4) 0.56851(16) -0.1807(3) 0.0305(8) Uani d . 1 C
H17 0.6393 0.6089 -0.2105 0.037 Uiso calc R 1 H
C18 0.7660(4) 0.54403(14) -0.0821(3) 0.0242(7) Uani d . 1 C
C19 0.5710(6) 0.83514(19) -0.1124(4) 0.0635(13) Uani d . 1 C
H19A 0.6261 0.8503 -0.1760 0.076 Uiso calc R 1 H
H19B 0.4420 0.8307 -0.1522 0.076 Uiso calc R 1 H
C20 0.6004(8) 0.8816(2) -0.0098(5) 0.0815(16) Uani d . 1 C
H20A 0.5382 0.8684 0.0501 0.122 Uiso calc R 1 H
H20B 0.5547 0.9218 -0.0443 0.122 Uiso calc R 1 H
H20C 0.7277 0.8850 0.0320 0.122 Uiso calc R 1 H
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'
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 N1 C3 . . 107.6(3)
C1 N1 C4 . . 121.6(3)
C3 N1 C4 . . 130.8(3)
C1 N2 C2 . . 108.5(3)
C1 N2 C19 . . 125.7(4)
C2 N2 C19 . . 125.8(3)
N2 C1 N1 . . 109.5(3)
N2 C1 H1 . . 125.2
N1 C1 H1 . . 125.2
C3 C2 N2 . . 106.9(3)
C3 C2 H2 . . 126.5
N2 C2 H2 . . 126.5
C2 C3 N1 . . 107.5(3)
C2 C3 H3 . . 126.2
N1 C3 H3 . . 126.2
N1 C4 C5 . . 116.7(3)
N1 C4 H4A . . 108.1
C5 C4 H4A . . 108.1
N1 C4 H4B . . 108.1
C5 C4 H4B . . 108.1
H4A C4 H4B . . 107.3
C18 C5 C6 . . 107.9(2)
C18 C5 C4 . . 114.2(3)
C6 C5 C4 . . 113.5(3)
C18 C5 C12 . 3_765 108.9(2)
C6 C5 C12 . 3_765 109.4(2)
C4 C5 C12 . 3_765 102.8(2)
C7 C6 C11 . . 118.9(3)
C7 C6 C5 . . 124.2(3)
C11 C6 C5 . . 116.8(3)
C6 C7 C8 . . 120.2(3)
C6 C7 H7 . . 119.9
C8 C7 H7 . . 119.9
C9 C8 C7 . . 120.6(3)
C9 C8 H8 . . 119.7
C7 C8 H8 . . 119.7
C8 C9 C10 . . 119.7(3)
C8 C9 H9 . . 120.1
C10 C9 H9 . . 120.1
C9 C10 C11 . . 120.2(3)
C9 C10 H10 . . 119.9
C11 C10 H10 . . 119.9
C10 C11 C6 . . 120.3(3)
C10 C11 C12 . . 121.5(3)
C6 C11 C12 . . 118.2(3)
C13 C12 C11 . . 109.4(2)
C13 C12 C5 . 3_765 112.3(3)
C11 C12 C5 . 3_765 112.5(2)
C13 C12 H12 . . 107.5
C11 C12 H12 . . 107.5
C5 C12 H12 3_765 . 107.5
C14 C13 C18 . . 119.7(3)
C14 C13 C12 . . 121.5(3)
C18 C13 C12 . . 118.8(3)
C15 C14 C13 . . 120.9(3)
C15 C14 H14 . . 119.5
C13 C14 H14 . . 119.5
C14 C15 C16 . . 119.7(3)
C14 C15 H15 . . 120.2
C16 C15 H15 . . 120.2
C15 C16 C17 . . 120.3(3)
C15 C16 H16 . . 119.9
C17 C16 H16 . . 119.9
C16 C17 C18 . . 120.7(3)
C16 C17 H17 . . 119.7
C18 C17 H17 . . 119.7
C17 C18 C13 . . 118.8(3)
C17 C18 C5 . . 125.0(3)
C13 C18 C5 . . 116.1(3)
C20 C19 N2 . . 112.3(4)
C20 C19 H19A . . 109.1
N2 C19 H19A . . 109.1
C20 C19 H19B . . 109.1
N2 C19 H19B . . 109.1
H19A C19 H19B . . 107.9
C19 C20 H20A . . 109.5
C19 C20 H20B . . 109.5
H20A C20 H20B . . 109.5
C19 C20 H20C . . 109.5
H20A C20 H20C . . 109.5
H20B C20 H20C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C1 . 1.334(4)
N1 C3 . 1.370(5)
N1 C4 . 1.476(4)
N2 C1 . 1.317(5)
N2 C2 . 1.371(5)
N2 C19 . 1.477(5)
C1 H1 . 0.9300
C2 C3 . 1.354(5)
C2 H2 . 0.9300
C3 H3 . 0.9300
C4 C5 . 1.541(4)
C4 H4A . 0.9700
C4 H4B . 0.9700
C5 C18 . 1.528(4)
C5 C6 . 1.530(4)
C5 C12 3_765 1.636(4)
C6 C7 . 1.391(4)
C6 C11 . 1.397(4)
C7 C8 . 1.393(5)
C7 H7 . 0.9300
C8 C9 . 1.374(5)
C8 H8 . 0.9300
C9 C10 . 1.386(5)
C9 H9 . 0.9300
C10 C11 . 1.391(4)
C10 H10 . 0.9300
C11 C12 . 1.521(4)
C12 C13 . 1.504(4)
C12 C5 3_765 1.636(4)
C12 H12 . 0.9800
C13 C14 . 1.383(4)
C13 C18 . 1.408(4)
C14 C15 . 1.376(5)
C14 H14 . 0.9300
C15 C16 . 1.382(5)
C15 H15 . 0.9300
C16 C17 . 1.385(5)
C16 H16 . 0.9300
C17 C18 . 1.387(4)
C17 H17 . 0.9300
C19 C20 . 1.469(6)
C19 H19A . 0.9700
C19 H19B . 0.9700
C20 H20A . 0.9600
C20 H20B . 0.9600
C20 H20C . 0.9600
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C2 N2 C1 N1 . . 0.0(4)
C19 N2 C1 N1 . . -178.8(3)
C3 N1 C1 N2 . . -0.3(4)
C4 N1 C1 N2 . . -179.9(3)
C1 N2 C2 C3 . . 0.2(4)
C19 N2 C2 C3 . . 179.1(4)
N2 C2 C3 N1 . . -0.4(4)
C1 N1 C3 C2 . . 0.4(4)
C4 N1 C3 C2 . . -180.0(3)
C1 N1 C4 C5 . . -164.2(3)
C3 N1 C4 C5 . . 16.2(5)
N1 C4 C5 C18 . . 56.1(4)
N1 C4 C5 C6 . . -68.1(4)
N1 C4 C5 C12 . 3_765 173.9(3)
C18 C5 C6 C7 . . -136.2(3)
C4 C5 C6 C7 . . -8.7(4)
C12 C5 C6 C7 3_765 . 105.4(3)
C18 C5 C6 C11 . . 46.8(4)
C4 C5 C6 C11 . . 174.4(3)
C12 C5 C6 C11 3_765 . -71.5(3)
C11 C6 C7 C8 . . -0.7(5)
C5 C6 C7 C8 . . -177.6(3)
C6 C7 C8 C9 . . 1.9(5)
C7 C8 C9 C10 . . -2.1(6)
C8 C9 C10 C11 . . 1.1(5)
C9 C10 C11 C6 . . 0.0(5)
C9 C10 C11 C12 . . -179.3(3)
C7 C6 C11 C10 . . -0.2(5)
C5 C6 C11 C10 . . 176.9(3)
C7 C6 C11 C12 . . 179.1(3)
C5 C6 C11 C12 . . -3.7(4)
C10 C11 C12 C13 . . 139.3(3)
C6 C11 C12 C13 . . -40.0(4)
C10 C11 C12 C5 . 3_765 -95.2(3)
C6 C11 C12 C5 . 3_765 85.5(3)
C11 C12 C13 C14 . . -140.8(3)
C5 C12 C13 C14 3_765 . 93.5(3)
C11 C12 C13 C18 . . 40.4(4)
C5 C12 C13 C18 3_765 . -85.3(3)
C18 C13 C14 C15 . . -1.1(5)
C12 C13 C14 C15 . . -179.9(3)
C13 C14 C15 C16 . . 0.2(5)
C14 C15 C16 C17 . . 0.4(5)
C15 C16 C17 C18 . . -0.1(5)
C16 C17 C18 C13 . . -0.7(5)
C16 C17 C18 C5 . . 176.1(3)
C14 C13 C18 C17 . . 1.3(5)
C12 C13 C18 C17 . . -179.8(3)
C14 C13 C18 C5 . . -175.8(3)
C12 C13 C18 C5 . . 3.1(4)
C6 C5 C18 C17 . . 136.7(3)
C4 C5 C18 C17 . . 9.6(5)
C12 C5 C18 C17 3_765 . -104.6(3)
C6 C5 C18 C13 . . -46.4(4)
C4 C5 C18 C13 . . -173.5(3)
C12 C5 C18 C13 3_765 . 72.3(3)
C1 N2 C19 C20 . . -116.5(5)
C2 N2 C19 C20 . . 64.8(6)
