#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/99/2239972.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_2239972
loop_
_publ_author_name
'Zimmermann, Iwan'
'Keene, Tony D.'
'Hauser, Jürg'
'Decurtins, Silvio'
'Liu, Shi-Xia'
_publ_section_title
;
 Crystal structures of isotypic poly[bis(benzimidazolium)
 [tetra-μ-iodido-stannate(II)]] and poly[bis(5,6-difluorobenzimidazolium)
 [tetra-μ-iodido-stannate(II)]]
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              178
_journal_page_last               182
_journal_paper_doi               10.1107/S1600536814019151
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          '(C7 H5 F2 N2)2 [Sn I4]'
_chemical_formula_moiety         '2(C7 H5 F2 N2 +), I4 Sn 2-'
_chemical_formula_sum            'C14 H10 F4 I4 N4 Sn'
_chemical_formula_weight         936.55
_chemical_name_systematic
;
Poly[bis(5,6-difluorobenzimidazolium) [tetra-μ-iodido-stannate(II)]]
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 109.3241(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   31.3825(6)
_cell_length_b                   6.18011(12)
_cell_length_c                   12.38507(13)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      65.437
_cell_measurement_theta_min      5.502
_cell_volume                     2266.72(7)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008) and VESTA (Momma & Izumi,
2011)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type
;
Bruker APEXII CCD
;
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            29697
_diffrn_reflns_theta_full        30.000
_diffrn_reflns_theta_max         33.085
_diffrn_reflns_theta_min         2.751
_exptl_absorpt_coefficient_mu    6.614
_exptl_absorpt_correction_T_max  0.522184
_exptl_absorpt_correction_T_min  0.321509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(TWINABS; Bruker, 2001)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.744
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.013
_refine_diff_density_max         1.951
_refine_diff_density_min         -1.739
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         5792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0948P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1241
_reflns_number_gt                5179
_reflns_number_total             5792
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wm5043sup1.cif
_cod_data_source_block           2
_cod_database_code               2239972
_cod_database_fobs_code          2239972
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           201.4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_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_occupancy
Sn Sn1 0.0000 0.05198(5) 0.2500 0.01458(10) Uani d 1
I I1 0.10663(2) 0.06742(4) 0.33581(3) 0.02019(10) Uani d 1
I I2 0.0000 0.0000 0.0000 0.02079(11) Uani d 1
I I3 0.0000 -0.45465(5) 0.2500 0.02092(11) Uani d 1
C C1 0.14859(19) 0.4618(7) 0.0571(4) 0.0227(9) Uani d 1
N N2 0.10624(15) 0.3704(7) 0.0285(3) 0.0249(8) Uani d 1
H H2 0.092(2) 0.260(10) -0.025(5) 0.030 Uiso d 1
C C3 0.08158(18) 0.4824(8) 0.0780(5) 0.0271(10) Uani d 1
H H3 0.0511 0.4521 0.0709 0.033 Uiso calc 1
N N4 0.10586(15) 0.6417(7) 0.1383(3) 0.0251(8) Uani d 1
H H4 0.099(2) 0.714(9) 0.178(5) 0.030 Uiso d 1
C C5 0.14871(16) 0.6384(8) 0.1291(4) 0.0232(9) Uani d 1
C C6 0.18595(18) 0.7714(8) 0.1732(4) 0.0283(10) Uani d 1
H H6 0.1860 0.8918 0.2210 0.034 Uiso calc 1
C C7 0.22244(18) 0.7166(9) 0.1429(5) 0.0319(11) Uani d 1
F F7 0.26085(11) 0.8325(7) 0.1827(3) 0.0460(9) Uani d 1
C C8 0.22240(19) 0.5394(9) 0.0718(5) 0.0307(12) Uani d 1
F F8 0.26118(12) 0.5015(6) 0.0508(4) 0.0447(8) Uani d 1
C C9 0.18591(19) 0.4095(9) 0.0276(4) 0.0279(10) Uani d 1
H H9 0.1861 0.2901 -0.0205 0.033 Uiso calc 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'
Sn Sn -0.6537 1.4246 '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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
I1 Sn1 I2 . . 89.374(6) y
I1 Sn1 I2 . 2 90.984(6) y
I1 Sn1 I1 . 2 176.539(14) y
I2 Sn1 I2 . 2 168.154(12) y
I1 Sn1 I3 . . 91.731(7) y
I2 Sn1 I3 . . 84.077(6) y
I1 Sn1 I3 . 1_565 88.269(7) y
I2 Sn1 I3 . 1_565 95.923(6) y
I3 Sn1 I3 . 1_565 180.0 y
I3 Sn1 I2 1_565 2 95.923(6) ?
I2 Sn1 I3 2 . 84.077(6) ?
I3 Sn1 I1 1_565 2 88.270(7) ?
I2 Sn1 I1 . 2 90.984(6) ?
I2 Sn1 I1 2 2 89.374(6) ?
I3 Sn1 I1 . 2 91.730(7) ?
Sn1 I2 Sn1 5 . 180.0 ?
Sn1 I3 Sn1 1_545 . 180.0 ?
C9 C1 N2 . . 131.9(4) ?
C9 C1 C5 . . 121.7(5) ?
N2 C1 C5 . . 106.3(4) ?
C3 N2 C1 . . 109.1(4) ?
C3 N2 H2 . . 119(3) ?
C1 N2 H2 . . 131(3) ?
N4 C3 N2 . . 109.6(5) ?
N4 C3 H3 . . 125.2 ?
N2 C3 H3 . . 125.2 ?
C3 N4 C5 . . 109.7(4) ?
C3 N4 H4 . . 125(5) ?
C5 N4 H4 . . 124(5) ?
C6 C5 N4 . . 132.3(4) ?
C6 C5 C1 . . 122.3(5) ?
N4 C5 C1 . . 105.3(4) ?
C7 C6 C5 . . 114.9(4) ?
C7 C6 H6 . . 122.6 ?
C5 C6 H6 . . 122.6 ?
F7 C7 C6 . . 119.9(5) ?
F7 C7 C8 . . 117.4(5) ?
C6 C7 C8 . . 122.7(5) ?
F8 C8 C9 . . 121.0(5) ?
F8 C8 C7 . . 116.3(5) ?
C9 C8 C7 . . 122.7(5) ?
C8 C9 C1 . . 115.6(5) ?
C8 C9 H9 . . 122.2 ?
C1 C9 H9 . . 122.2 ?
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
Sn1 I1 . 3.1596(3) y
Sn1 I2 . 3.11289(5) y
Sn1 I3 . 3.1310(5) y
Sn1 I3 1_565 3.0491(5) y
Sn1 I1 2 3.1596(3) ?
C1 C9 . 1.376(7) ?
C1 N2 . 1.378(7) ?
C1 C5 . 1.408(6) ?
N2 C3 . 1.330(7) ?
N2 H2 . 0.95(6) ?
C3 N4 . 1.316(7) ?
C3 H3 . 0.9500 ?
N4 C5 . 1.387(6) ?
N4 H4 . 0.75(5) ?
C5 C6 . 1.385(7) ?
C6 C7 . 1.361(7) ?
C6 H6 . 0.9500 ?
C7 F7 . 1.348(6) ?
C7 C8 . 1.404(7) ?
C8 F8 . 1.347(6) ?
C8 C9 . 1.357(8) ?
C9 H9 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2 I1 6 0.95(6) 2.79(6) 3.610(4) 145(4)
N4 H4 I1 1_565 0.75(5) 2.88(6) 3.587(4) 157(6)
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
C9 C1 N2 C3 -179.2(6)
C5 C1 N2 C3 0.5(6)
C1 N2 C3 N4 -0.5(6)
N2 C3 N4 C5 0.2(6)
C3 N4 C5 C6 178.4(5)
C3 N4 C5 C1 0.1(6)
C9 C1 C5 C6 0.9(8)
N2 C1 C5 C6 -178.9(4)
C9 C1 C5 N4 179.4(5)
N2 C1 C5 N4 -0.4(5)
N4 C5 C6 C7 -178.9(5)
C1 C5 C6 C7 -0.8(7)
C5 C6 C7 F7 -178.7(5)
C5 C6 C7 C8 0.3(8)
F7 C7 C8 F8 0.4(8)
C6 C7 C8 F8 -178.7(5)
F7 C7 C8 C9 179.2(5)
C6 C7 C8 C9 0.2(9)
F8 C8 C9 C1 178.7(5)
C7 C8 C9 C1 -0.2(8)
N2 C1 C9 C8 179.4(5)
C5 C1 C9 C8 -0.4(8)
