#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/31/2223145.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_2223145
loop_
_publ_author_name
'Lee, See Mun'
'Lo, Kong Mun'
'Mohd Ali, Hapipah'
'Robinson, Ward T.'
_publ_section_title
;
 Bis[4-(dimethylamino)pyridinium]
 tetrabromidobis(4-methylphenyl)stannate(IV)
;
_journal_coeditor_code           LH2842
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1040
_journal_paper_doi               10.1107/S1600536809030323
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '(C7 H11 N2)2 [Sn Br4 (C7 H7)2]'
_chemical_formula_moiety         '2(C7 H11 N2 +), C14 H14 Br4 Sn 2-'
_chemical_formula_sum            'C28 H36 Br4 N4 Sn'
_chemical_formula_weight         866.94
_chemical_name_systematic
;
Bis[4-(dimethylamino)pyridinium] tetrabromidobis(4-methylphenyl)stannate(IV)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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
_cell_angle_beta                 95.0630(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2178(3)
_cell_length_b                   10.4808(3)
_cell_length_c                   14.5833(3)
_cell_measurement_reflns_used    6698
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.34
_cell_volume                     1555.64(7)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       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  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11555
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    5.982
_exptl_absorpt_correction_T_max  0.353
_exptl_absorpt_correction_T_min  0.229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             844
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.452
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0176
_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)+(0.0246P)²+0.5727P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0438
_refine_ls_wR_factor_ref         0.0452
_reflns_number_gt                3225
_reflns_number_total             3569
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2842.cif
_cod_data_source_block           I
_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_sg_symbol_H-M      'P 21/n'
_cod_database_code               2223145
_cod_database_fobs_code          2223145
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn Sn1 1.0000 0.0000 0.0000 0.01042(5) Uani d S 1 . .
Br Br1 0.951470(19) -0.180492(17) 0.131083(12) 0.01383(5) Uani d . 1 . .
Br Br2 1.261950(18) -0.018292(18) 0.055861(14) 0.01597(6) Uani d . 1 . .
N N1 0.24150(18) 0.65685(17) 0.11335(13) 0.0237(4) Uani d . 1 . .
H H1 0.2028 0.7281 0.1280 0.028 Uiso calc R 1 . .
N N2 0.43055(16) 0.33066(16) 0.04249(11) 0.0166(3) Uani d . 1 . .
C C1 0.98097(18) 0.15055(17) 0.09731(12) 0.0106(3) Uani d . 1 . .
C C2 1.06827(19) 0.25260(18) 0.10370(13) 0.0140(4) Uani d . 1 . .
H H2 1.1417 0.2527 0.0680 0.017 Uiso calc R 1 . .
C C3 1.04872(19) 0.35431(19) 0.16189(13) 0.0158(4) Uani d . 1 . .
H H3 1.1089 0.4236 0.1651 0.019 Uiso calc R 1 . .
C C4 0.94235(19) 0.35675(19) 0.21573(13) 0.0148(4) Uani d . 1 . .
C C5 0.85693(19) 0.25278(19) 0.21028(13) 0.0142(4) Uani d . 1 . .
H H5 0.7847 0.2514 0.2471 0.017 Uiso calc R 1 . .
C C6 0.87603(18) 0.15088(18) 0.15165(12) 0.0136(4) Uani d . 1 . .
H H6 0.8167 0.0809 0.1488 0.016 Uiso calc R 1 . .
C C7 0.9200(2) 0.46954(19) 0.27623(15) 0.0204(4) Uani d . 1 . .
H H7A 0.8970 0.5443 0.2377 0.031 Uiso calc R 1 . .
H H7B 1.0004 0.4873 0.3160 0.031 Uiso calc R 1 . .
H H7C 0.8482 0.4506 0.3144 0.031 Uiso calc R 1 . .
C C8 0.2184(2) 0.6093(2) 0.02768(15) 0.0249(5) Uani d . 1 . .
H H8 0.1593 0.6526 -0.0157 0.030 Uiso calc R 1 . .
C C9 0.2777(2) 0.5010(2) 0.00204(15) 0.0201(4) Uani d . 1 . .
H H9 0.2596 0.4687 -0.0586 0.024 Uiso calc R 1 . .
C C10 0.36716(18) 0.43551(18) 0.06587(13) 0.0131(4) Uani d . 1 . .
C C11 0.3857(2) 0.48772(18) 0.15624(14) 0.0171(4) Uani d . 1 . .
H H11 0.4421 0.4461 0.2022 0.021 Uiso calc R 1 . .
C C12 0.3229(2) 0.5969(2) 0.17697(14) 0.0202(4) Uani d . 1 . .
H H12 0.3367 0.6314 0.2373 0.024 Uiso calc R 1 . .
C C13 0.4097(2) 0.2765(2) -0.05001(14) 0.0208(4) Uani d . 1 . .
H H13A 0.3200 0.2431 -0.0599 0.031 Uiso calc R 1 . .
H H13B 0.4726 0.2072 -0.0565 0.031 Uiso calc R 1 . .
H H13C 0.4225 0.3430 -0.0956 0.031 Uiso calc R 1 . .
C C14 0.5171(2) 0.2619(2) 0.11039(15) 0.0249(5) Uani d . 1 . .
H H14A 0.5837 0.3204 0.1387 0.037 Uiso calc R 1 . .
H H14B 0.5603 0.1920 0.0801 0.037 Uiso calc R 1 . .
H H14C 0.4653 0.2270 0.1580 0.037 Uiso calc R 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'
Br Br -0.2901 2.4595 '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'
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
C1 Sn1 C1 3_755 . 180.00(13) ?
C1 Sn1 Br2 3_755 3_755 89.88(5) ?
C1 Sn1 Br2 . 3_755 90.12(5) ?
C1 Sn1 Br2 3_755 . 90.12(5) ?
C1 Sn1 Br2 . . 89.88(5) ?
Br2 Sn1 Br2 3_755 . 180.000(12) ?
C1 Sn1 Br1 3_755 . 89.22(5) ?
C1 Sn1 Br1 . . 90.78(5) ?
Br2 Sn1 Br1 3_755 . 91.340(6) ?
Br2 Sn1 Br1 . . 88.660(6) ?
C1 Sn1 Br1 3_755 3_755 90.78(5) ?
C1 Sn1 Br1 . 3_755 89.22(5) ?
Br2 Sn1 Br1 3_755 3_755 88.660(6) ?
Br2 Sn1 Br1 . 3_755 91.340(6) ?
Br1 Sn1 Br1 . 3_755 180.000(10) ?
C12 N1 C8 . . 120.94(19) ?
C12 N1 H1 . . 119.5 ?
C8 N1 H1 . . 119.5 ?
C10 N2 C14 . . 120.81(17) ?
C10 N2 C13 . . 121.38(17) ?
C14 N2 C13 . . 117.71(17) ?
C6 C1 C2 . . 118.88(17) ?
C6 C1 Sn1 . . 119.98(13) ?
C2 C1 Sn1 . . 121.04(13) ?
C3 C2 C1 . . 120.37(17) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C2 C3 C4 . . 121.28(18) ?
C2 C3 H3 . . 119.4 ?
C4 C3 H3 . . 119.4 ?
C5 C4 C3 . . 117.91(17) ?
C5 C4 C7 . . 121.42(17) ?
C3 C4 C7 . . 120.66(18) ?
C6 C5 C4 . . 120.90(17) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C1 C6 C5 . . 120.63(18) ?
C1 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C4 C7 H7A . . 109.5 ?
C4 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C4 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N1 C8 C9 . . 121.3(2) ?
N1 C8 H8 . . 119.3 ?
C9 C8 H8 . . 119.3 ?
C8 C9 C10 . . 120.1(2) ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
N2 C10 C9 . . 121.88(18) ?
N2 C10 C11 . . 121.65(18) ?
C9 C10 C11 . . 116.47(18) ?
C12 C11 C10 . . 120.16(19) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
N1 C12 C11 . . 121.0(2) ?
N1 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
N2 C13 H13A . . 109.5 ?
N2 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
N2 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N2 C14 H14A . . 109.5 ?
N2 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
N2 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 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
Sn1 C1 3_755 2.1424(18) ?
Sn1 C1 . 2.1424(18) ?
Sn1 Br2 3_755 2.7349(2) ?
Sn1 Br2 . 2.7349(2) ?
Sn1 Br1 . 2.76515(18) ?
Sn1 Br1 3_755 2.76515(18) ?
N1 C12 . 1.346(3) ?
N1 C8 . 1.346(3) ?
N1 H1 . 0.8800 ?
N2 C10 . 1.335(2) ?
N2 C14 . 1.459(3) ?
N2 C13 . 1.462(3) ?
C1 C6 . 1.388(3) ?
C1 C2 . 1.391(3) ?
C2 C3 . 1.388(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.396(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.394(3) ?
C4 C7 . 1.504(3) ?
C5 C6 . 1.393(3) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 C9 . 1.356(3) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.422(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.424(3) ?
C11 C12 . 1.359(3) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
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
N1 H1 Br1 1_465 0.88 2.75 3.448(2) 138
N1 H1 Br2 1_465 0.88 2.94 3.517(2) 125
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 Sn1 C1 C6 3_755 . . . 0.00(18) ?
Br2 Sn1 C1 C6 3_755 . . . 44.67(14) ?
Br2 Sn1 C1 C6 . . . . -135.33(14) ?
Br1 Sn1 C1 C6 . . . . -46.67(14) ?
Br1 Sn1 C1 C6 3_755 . . . 133.33(14) ?
C1 Sn1 C1 C2 3_755 . . . 0.00(7) ?
Br2 Sn1 C1 C2 3_755 . . . -131.72(15) ?
Br2 Sn1 C1 C2 . . . . 48.28(15) ?
Br1 Sn1 C1 C2 . . . . 136.94(15) ?
Br1 Sn1 C1 C2 3_755 . . . -43.06(15) ?
C6 C1 C2 C3 . . . . -1.5(3) ?
Sn1 C1 C2 C3 . . . . 174.92(14) ?
C1 C2 C3 C4 . . . . 0.5(3) ?
C2 C3 C4 C5 . . . . 0.9(3) ?
C2 C3 C4 C7 . . . . -178.05(19) ?
C3 C4 C5 C6 . . . . -1.1(3) ?
C7 C4 C5 C6 . . . . 177.77(18) ?
C2 C1 C6 C5 . . . . 1.2(3) ?
Sn1 C1 C6 C5 . . . . -175.23(14) ?
C4 C5 C6 C1 . . . . 0.1(3) ?
C12 N1 C8 C9 . . . . -1.1(3) ?
N1 C8 C9 C10 . . . . -0.4(3) ?
C14 N2 C10 C9 . . . . -177.10(19) ?
C13 N2 C10 C9 . . . . -0.9(3) ?
C14 N2 C10 C11 . . . . 2.9(3) ?
C13 N2 C10 C11 . . . . 179.12(18) ?
C8 C9 C10 N2 . . . . -178.0(2) ?
C8 C9 C10 C11 . . . . 2.0(3) ?
N2 C10 C11 C12 . . . . 177.86(18) ?
C9 C10 C11 C12 . . . . -2.1(3) ?
C8 N1 C12 C11 . . . . 1.0(3) ?
C10 C11 C12 N1 . . . . 0.7(3) ?
