#------------------------------------------------------------------------------
#$Date: 2016-03-23 02:51:16 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179211 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/41/4314185.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_4314185
loop_
_publ_author_name
'Cheng-Yong Su'
'Andrea M. Goforth'
'Mark D. Smith'
'Hans-Conrad zur Loye'
_publ_section_title
;
 Formation of Dinuclear, Macrocyclic, and Chain Structures from HgI2 and a
 Semirigid Benzimidazole-Based Bridging Ligand: An Example of Ring-Opening
 Supramolecular Isomerism
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5685
_journal_page_last               5692
_journal_paper_doi               10.1021/ic034388l
_journal_volume                  42
_journal_year                    2003
_chemical_formula_sum            'C25 H24 Hg2 I4 N4'
_chemical_formula_weight         1289.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 90.910(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.0385(8)
_cell_length_b                   19.1301(18)
_cell_length_c                   9.8324(9)
_cell_measurement_reflns_used    9135
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      26.406
_cell_measurement_theta_min      2.329
_cell_volume                     1511.8(2)
_computing_cell_refinement       'SAINT+ NT V6.02a (Bruker, 1998)'
_computing_data_collection       'SMART NT V5.625 (Bruker, 1998)'
_computing_data_reduction        'SAINT+ NT V6.02a'
_computing_molecular_graphics    'SHELXTL V5.1 (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL V5.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150.0(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11981
_diffrn_reflns_theta_full        26.43
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    14.248
_exptl_absorpt_correction_T_max  0.2603
_exptl_absorpt_correction_T_min  0.1303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS, Bruker, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.832
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1148
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_refine_diff_density_max         2.307
_refine_diff_density_min         -1.044
_refine_diff_density_rms         0.197
_refine_ls_extinction_coef       0.00056(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0361P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0706
_reflns_number_gt                2797
_reflns_number_total             3194
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic034388lsi20030709_115411_2.cif
_cod_data_source_block           compd1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4314185
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg Hg 0.32723(3) 0.652586(14) 0.69362(2) 0.03397(10) Uani 1 1 d . . .
I1 I 0.20207(5) 0.58119(2) 0.89737(4) 0.03199(13) Uani 1 1 d . . .
I2 I 0.08509(7) 0.7500 0.58263(6) 0.03480(16) Uani 1 2 d S . .
I3 I 0.58964(7) 0.7500 0.73818(6) 0.03260(16) Uani 1 2 d S . .
C1 C 0.5092(7) 0.6348(3) 0.4084(6) 0.0267(13) Uani 1 1 d . . .
H1 H 0.5726 0.6757 0.4264 0.032 Uiso 1 1 calc R . .
C2 C 0.3399(7) 0.5471(3) 0.4319(6) 0.0239(12) Uani 1 1 d . . .
C3 C 0.2253(7) 0.4983(3) 0.4786(7) 0.0300(14) Uani 1 1 d . . .
H3 H 0.1801 0.5012 0.5671 0.036 Uiso 1 1 calc R . .
C4 C 0.1813(7) 0.4458(3) 0.3896(7) 0.0330(15) Uani 1 1 d . . .
H4 H 0.1033 0.4116 0.4177 0.040 Uiso 1 1 calc R . .
C5 C 0.2466(8) 0.4409(3) 0.2602(7) 0.0319(14) Uani 1 1 d . . .
H5 H 0.2129 0.4034 0.2028 0.038 Uiso 1 1 calc R . .
C6 C 0.3601(7) 0.4895(3) 0.2123(6) 0.0263(13) Uani 1 1 d . . .
H6 H 0.4044 0.4865 0.1235 0.032 Uiso 1 1 calc R . .
C7 C 0.4050(7) 0.5427(3) 0.3014(6) 0.0234(12) Uani 1 1 d . . .
C8 C 0.6035(8) 0.6182(3) 0.1656(6) 0.0302(14) Uani 1 1 d . . .
H8A H 0.5241 0.6212 0.0878 0.036 Uiso 1 1 calc R . .
H8B H 0.6846 0.5808 0.1454 0.036 Uiso 1 1 calc R . .
C9 C 0.6940(7) 0.6865(3) 0.1802(6) 0.0226(12) Uani 1 1 d . . .
C10 C 0.8657(7) 0.6870(3) 0.2104(6) 0.0258(13) Uani 1 1 d . . .
C11 C 0.9468(10) 0.7500 0.2219(9) 0.0289(19) Uani 1 2 d S . .
H11 H 1.0636 0.7500 0.2386 0.035 Uiso 1 2 calc SR . .
C12 C 0.6071(10) 0.7500 0.1649(8) 0.0232(17) Uani 1 2 d S . .
C13 C 0.9615(8) 0.6200(4) 0.2341(7) 0.0373(16) Uani 1 1 d . . .
H13A H 1.0794 0.6308 0.2496 0.056 Uiso 1 1 calc R . .
H13B H 0.9494 0.5897 0.1541 0.056 Uiso 1 1 calc R . .
H13C H 0.9177 0.5959 0.3140 0.056 Uiso 1 1 calc R . .
C14 C 0.4228(10) 0.7500 0.1357(9) 0.031(2) Uani 1 2 d S . .
H14A H 0.3965 0.7500 0.0380 0.046 Uiso 1 2 d SR . .
H14B H 0.3671 0.7090 0.1737 0.046 Uiso 1 1 d R . .
N1 N 0.4082(6) 0.6059(3) 0.4972(5) 0.0258(11) Uani 1 1 d . . .
N2 N 0.5123(6) 0.5995(3) 0.2891(5) 0.0246(11) 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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 '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
_geom_angle_publ_flag
N1 Hg I1 124.72(13) . . ?
N1 Hg I3 99.77(12) . . ?
I1 Hg I3 120.891(18) . . ?
N1 Hg I2 97.74(13) . . ?
I1 Hg I2 110.935(18) . . ?
I3 Hg I2 97.404(15) . . ?
Hg I2 Hg 80.116(19) 4_575 . ?
Hg I3 Hg 81.899(19) . 4_575 ?
N1 C1 N2 112.6(5) . . ?
C3 C2 C7 121.5(6) . . ?
C3 C2 N1 129.9(6) . . ?
C7 C2 N1 108.6(5) . . ?
C4 C3 C2 116.3(6) . . ?
C3 C4 C5 122.4(6) . . ?
C4 C5 C6 121.7(6) . . ?
C7 C6 C5 116.3(6) . . ?
C6 C7 N2 132.2(5) . . ?
C6 C7 C2 121.8(5) . . ?
N2 C7 C2 105.9(5) . . ?
N2 C8 C9 112.3(5) . . ?
C10 C9 C12 120.0(6) . . ?
C10 C9 C8 119.9(5) . . ?
C12 C9 C8 120.1(5) . . ?
C11 C10 C9 119.0(6) . . ?
C11 C10 C13 119.4(6) . . ?
C9 C10 C13 121.5(6) . . ?
C10 C11 C10 122.6(8) 4_575 . ?
C9 C12 C9 119.2(7) 4_575 . ?
C9 C12 C14 120.4(4) 4_575 . ?
C9 C12 C14 120.4(4) . . ?
C1 N1 C2 105.8(5) . . ?
C1 N1 Hg 126.4(4) . . ?
C2 N1 Hg 126.8(4) . . ?
C1 N2 C7 107.0(5) . . ?
C1 N2 C8 127.6(5) . . ?
C7 N2 C8 125.3(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg N1 2.234(5) . ?
Hg I1 2.6372(5) . ?
Hg I3 2.8434(5) . ?
Hg I2 2.8957(5) . ?
I2 Hg 2.8957(5) 4_575 ?
I3 Hg 2.8434(5) 4_575 ?
C1 N1 1.322(8) . ?
C1 N2 1.354(7) . ?
C2 C3 1.394(8) . ?
C2 C7 1.395(8) . ?
C2 N1 1.403(7) . ?
C3 C4 1.374(9) . ?
C4 C5 1.387(9) . ?
C5 C6 1.390(8) . ?
C6 C7 1.386(8) . ?
C7 N2 1.395(7) . ?
C8 N2 1.472(7) . ?
C8 C9 1.502(9) . ?
C9 C10 1.407(8) . ?
C9 C12 1.408(7) . ?
C10 C11 1.375(7) . ?
C10 C13 1.512(9) . ?
C11 C10 1.375(7) 4_575 ?
C12 C9 1.408(7) 4_575 ?
C12 C14 1.504(11) . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Hg I2 Hg -114.38(12) . . . 4_575 ?
I1 Hg I2 Hg 113.752(16) . . . 4_575 ?
I3 Hg I2 Hg -13.41(2) . . . 4_575 ?
N1 Hg I3 Hg 112.80(13) . . . 4_575 ?
I1 Hg I3 Hg -106.252(17) . . . 4_575 ?
I2 Hg I3 Hg 13.59(2) . . . 4_575 ?
C7 C2 C3 C4 0.4(8) . . . . ?
N1 C2 C3 C4 179.7(6) . . . . ?
C2 C3 C4 C5 0.1(9) . . . . ?
C3 C4 C5 C6 -0.6(9) . . . . ?
C4 C5 C6 C7 0.5(9) . . . . ?
C5 C6 C7 N2 -179.6(6) . . . . ?
C5 C6 C7 C2 0.0(8) . . . . ?
C3 C2 C7 C6 -0.4(8) . . . . ?
N1 C2 C7 C6 -179.9(5) . . . . ?
C3 C2 C7 N2 179.3(5) . . . . ?
N1 C2 C7 N2 -0.2(6) . . . . ?
N2 C8 C9 C10 100.0(6) . . . . ?
N2 C8 C9 C12 -79.6(7) . . . . ?
C12 C9 C10 C11 -1.2(9) . . . . ?
C8 C9 C10 C11 179.3(6) . . . . ?
C12 C9 C10 C13 177.1(6) . . . . ?
C8 C9 C10 C13 -2.5(8) . . . . ?
C9 C10 C11 C10 2.5(12) . . . 4_575 ?
C13 C10 C11 C10 -175.7(6) . . . 4_575 ?
C10 C9 C12 C9 -0.1(11) . . . 4_575 ?
C8 C9 C12 C9 179.4(4) . . . 4_575 ?
C10 C9 C12 C14 -178.7(6) . . . . ?
C8 C9 C12 C14 0.9(10) . . . . ?
N2 C1 N1 C2 0.2(7) . . . . ?
N2 C1 N1 Hg -169.3(4) . . . . ?
C3 C2 N1 C1 -179.5(6) . . . . ?
C7 C2 N1 C1 0.0(6) . . . . ?
C3 C2 N1 Hg -10.0(8) . . . . ?
C7 C2 N1 Hg 169.5(4) . . . . ?
I1 Hg N1 C1 -161.0(4) . . . . ?
I3 Hg N1 C1 -22.1(5) . . . . ?
I2 Hg N1 C1 76.8(5) . . . . ?
I1 Hg N1 C2 31.6(5) . . . . ?
I3 Hg N1 C2 170.5(4) . . . . ?
I2 Hg N1 C2 -90.6(4) . . . . ?
N1 C1 N2 C7 -0.4(7) . . . . ?
N1 C1 N2 C8 176.8(5) . . . . ?
C6 C7 N2 C1 -180.0(6) . . . . ?
C2 C7 N2 C1 0.3(6) . . . . ?
C6 C7 N2 C8 2.8(10) . . . . ?
C2 C7 N2 C8 -176.9(5) . . . . ?
C9 C8 N2 C1 -2.9(8) . . . . ?
C9 C8 N2 C7 173.8(5) . . . . ?
