#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007099.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_2007099
loop_
_publ_author_name
'Hensen, K.'
'Kettner, M.'
'Bolte, M.'
_publ_section_title
;
 Bromo(hydrido)methylbis(4-methylpyridine-<i>N</i>)silicon Bromide at
 173K
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              358
_journal_page_last               359
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C13 H18 Br N2 Si 1+, Br 1-'
_chemical_formula_sum            'C13 H18 Br2 N2 Si'
_chemical_formula_weight         390.20
_chemical_name_systematic
;
Bromohydridomethyl-bis-(4-Methylpyridinium)-siliciumbromid
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.39720(10)
_cell_length_b                   12.39170(10)
_cell_length_c                   13.7857(2)
_cell_measurement_reflns_used    5772
_cell_measurement_temperature    173
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1
_cell_volume                     1605.31(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL96 (Sheldrick, 1996b)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173
_diffrn_measurement_device       'Siemens CCD three-circle diffractometer'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'highly oriented graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.055
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17926
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  840
_diffrn_standards_number         305
_exptl_absorpt_coefficient_mu    5.111
_exptl_absorpt_correction_T_max  0.600
_exptl_absorpt_correction_T_min  0.383
_exptl_absorpt_correction_type   'Empirical using SADABS (Sheldrick, 1996a)'
_exptl_crystal_colour            'colourless, transparent'
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.399
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.003(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.001
_refine_ls_goodness_of_fit_obs   1.033
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_restrained_S_obs      1.033
_refine_ls_R_factor_all          0.033
_refine_ls_R_factor_obs          0.024
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0135P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.043
_refine_ls_wR_factor_obs         0.042
_reflns_number_observed          2576
_reflns_number_total             2950
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    ka1258.cif
_[local]_cod_data_source_block   he2sad
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_database_code               2007099
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Si1 0.0174(5) 0.0211(5) 0.0266(5) -0.0011(4) 0.0024(4) -0.0021(4)
Br1 0.02886(18) 0.03638(18) 0.03252(19) -0.00514(18) -0.00489(18) 0.00626(15)
Br2 0.02705(18) 0.02859(17) 0.0443(2) -0.00035(17) 0.00776(19) 0.00357(15)
C1 0.0207(17) 0.0255(17) 0.0278(17) 0.0012(15) -0.0004(14) -0.0028(15)
N1 0.0222(15) 0.0205(14) 0.0244(15) -0.0002(11) 0.0027(12) -0.0004(11)
C2 0.0260(19) 0.0250(15) 0.0203(15) 0.0048(16) 0.0013(14) 0.0009(14)
C3 0.0167(17) 0.039(2) 0.0224(18) 0.0013(14) 0.0020(14) 0.0042(16)
C4 0.027(2) 0.036(2) 0.0218(17) -0.0083(15) -0.0037(14) 0.0064(15)
C5 0.039(2) 0.0178(17) 0.0351(19) -0.0024(15) -0.0047(19) 0.0011(14)
C6 0.0203(17) 0.0288(19) 0.032(2) 0.0029(14) 0.0030(16) -0.0019(15)
C7 0.032(2) 0.047(2) 0.043(2) -0.0195(18) -0.0041(17) 0.0077(18)
N11 0.0167(13) 0.0217(13) 0.0238(13) 0.0002(14) 0.0025(13) -0.0059(11)
C12 0.0223(18) 0.0220(18) 0.0330(19) 0.0054(13) 0.0017(15) -0.0030(15)
C13 0.0154(17) 0.033(2) 0.031(2) 0.0002(15) 0.0020(14) -0.0010(15)
C14 0.0233(18) 0.0304(19) 0.0207(18) -0.0034(15) -0.0016(15) 0.0038(14)
C15 0.0264(19) 0.0192(17) 0.0254(18) 0.0020(13) 0.0004(13) 0.0021(13)
C16 0.0198(18) 0.029(2) 0.0199(17) 0.0046(14) 0.0027(13) -0.0018(14)
C17 0.0287(19) 0.033(2) 0.042(2) -0.0103(15) -0.0038(18) 0.0103(17)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Si1 0.43382(9) 0.33706(7) 0.12942(6) 0.0217(2) Uani d . 1 Si
H1 0.525(3) 0.259(2) 0.0972(19) 0.026 Uiso d . 1 H
Br1 0.29361(4) 0.40544(2) 0.00928(2) 0.03259(9) Uani d . 1 Br
Br2 0.70457(4) 0.21180(2) 0.29631(2) 0.03331(9) Uani d . 1 Br
C1 0.3992(3) 0.3989(3) 0.25086(19) 0.0246(7) Uani d . 1 C
H1A 0.4759 0.3791 0.2956 0.037 Uiso calc R 1 H
H1B 0.3083 0.3724 0.2762 0.037 Uiso calc R 1 H
H1C 0.3954 0.4776 0.2444 0.037 Uiso calc R 1 H
N1 0.5927(3) 0.44141(19) 0.09952(17) 0.0223(6) Uani d . 1 N
C2 0.7259(3) 0.4016(2) 0.09008(19) 0.0238(7) Uani d . 1 C
H2 0.7404 0.3261 0.0960 0.029 Uiso calc R 1 H
C3 0.8416(3) 0.4676(3) 0.0721(2) 0.0261(8) Uani d . 1 C
H3 0.9336 0.4364 0.0664 0.031 Uiso calc R 1 H
C4 0.8260(3) 0.5786(3) 0.0620(2) 0.0282(8) Uani d . 1 C
C5 0.6876(4) 0.6188(2) 0.0732(2) 0.0308(8) Uani d . 1 C
H5 0.6709 0.6942 0.0684 0.037 Uiso calc R 1 H
C6 0.5747(3) 0.5493(2) 0.0912(2) 0.0272(8) Uani d . 1 C
H6 0.4818 0.5785 0.0979 0.033 Uiso calc R 1 H
C7 0.9495(4) 0.6522(3) 0.0401(3) 0.0410(10) Uani d . 1 C
H7A 0.9605 0.7045 0.0928 0.061 Uiso calc R 1 H
H7B 0.9315 0.6906 -0.0209 0.061 Uiso calc R 1 H
H7C 1.0367 0.6094 0.0340 0.061 Uiso calc R 1 H
N11 0.2949(3) 0.21498(18) 0.15167(16) 0.0207(5) Uani d . 1 N
C12 0.1541(3) 0.2312(3) 0.1652(2) 0.0258(8) Uani d . 1 C
H12 0.1194 0.3033 0.1643 0.031 Uiso calc R 1 H
C13 0.0577(3) 0.1485(3) 0.1804(2) 0.0264(8) Uani d . 1 C
H13 -0.0404 0.1639 0.1896 0.032 Uiso calc R 1 H
C14 0.1068(3) 0.0418(3) 0.1819(2) 0.0248(7) Uani d . 1 C
C15 0.2524(3) 0.0246(2) 0.1704(2) 0.0236(8) Uani d . 1 C
H15 0.2897 -0.0466 0.1725 0.028 Uiso calc R 1 H
C16 0.3430(3) 0.1116(2) 0.1560(2) 0.0229(8) Uani d . 1 C
H16 0.4420 0.0985 0.1489 0.028 Uiso calc R 1 H
C17 0.0041(3) -0.0503(3) 0.1945(2) 0.0346(9) Uani d . 1 C
H17A 0.0563 -0.1152 0.2142 0.052 Uiso calc R 1 H
H17B -0.0450 -0.0640 0.1329 0.052 Uiso calc R 1 H
H17C -0.0659 -0.0318 0.2444 0.052 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'
Si Si 0.0817 0.0704 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
H1 Si1 C1 133.6(11) y
H1 Si1 N1 85.7(11) y
C1 Si1 N1 92.81(12) y
H1 Si1 N11 85.6(11) y
C1 Si1 N11 93.35(12) y
N1 Si1 N11 171.27(11) y
H1 Si1 Br1 112.9(11) y
C1 Si1 Br1 113.44(10) y
N1 Si1 Br1 92.35(8) y
N11 Si1 Br1 90.87(8) y
C2 N1 C6 117.9(3) ?
C2 N1 Si1 118.1(2) ?
C6 N1 Si1 123.9(2) ?
N1 C2 C3 122.0(3) ?
C2 C3 C4 121.3(3) ?
C3 C4 C5 116.0(3) ?
C3 C4 C7 122.5(3) ?
C5 C4 C7 121.4(3) ?
C6 C5 C4 120.5(3) ?
N1 C6 C5 122.2(3) ?
C12 N11 C16 117.4(3) ?
C12 N11 Si1 122.8(2) ?
C16 N11 Si1 119.8(2) ?
N11 C12 C13 123.4(3) ?
C12 C13 C14 119.1(3) ?
C15 C14 C13 117.7(3) ?
C15 C14 C17 121.8(3) ?
C13 C14 C17 120.4(3) ?
C16 C15 C14 120.0(3) ?
N11 C16 C15 122.3(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Si1 H1 1.37(3) y
Si1 C1 1.870(3) y
Si1 N1 2.018(3) y
Si1 N11 2.021(2) y
Si1 Br1 2.2797(9) y
N1 C2 1.351(4) ?
N1 C6 1.352(4) ?
C2 C3 1.383(4) ?
C3 C4 1.390(4) ?
C4 C5 1.401(5) ?
C4 C7 1.506(4) ?
C5 C6 1.390(4) ?
N11 C12 1.352(4) ?
N11 C16 1.359(4) ?
C12 C13 1.384(4) ?
C13 C14 1.401(4) ?
C14 C15 1.394(4) ?
C14 C17 1.505(4) ?
C15 C16 1.388(4) ?
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
H1 Si1 N1 C2 -18.5(11)
C1 Si1 N1 C2 115.1(2)
N11 Si1 N1 C2 -19.7(8)
Br1 Si1 N1 C2 -131.3(2)
H1 Si1 N1 C6 163.6(11)
C1 Si1 N1 C6 -62.8(3)
N11 Si1 N1 C6 162.3(6)
Br1 Si1 N1 C6 50.8(2)
C6 N1 C2 C3 -0.3(4)
Si1 N1 C2 C3 -178.3(2)
N1 C2 C3 C4 -0.5(5)
C2 C3 C4 C5 1.3(4)
C2 C3 C4 C7 -178.5(3)
C3 C4 C5 C6 -1.3(4)
C7 C4 C5 C6 178.5(3)
C2 N1 C6 C5 0.2(4)
Si1 N1 C6 C5 178.2(2)
C4 C5 C6 N1 0.6(5)
H1 Si1 N11 C12 -163.9(11)
C1 Si1 N11 C12 62.5(2)
N1 Si1 N11 C12 -162.6(6)
Br1 Si1 N11 C12 -51.0(2)
H1 Si1 N11 C16 17.9(11)
C1 Si1 N11 C16 -115.7(2)
N1 Si1 N11 C16 19.1(8)
Br1 Si1 N11 C16 130.8(2)
C16 N11 C12 C13 -1.9(4)
Si1 N11 C12 C13 179.9(2)
N11 C12 C13 C14 0.0(5)
C12 C13 C14 C15 1.6(5)
C12 C13 C14 C17 -177.7(3)
C13 C14 C15 C16 -1.3(5)
C17 C14 C15 C16 178.0(3)
C12 N11 C16 C15 2.2(4)
Si1 N11 C16 C15 -179.5(2)
C14 C15 C16 N11 -0.6(4)