#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2222417.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_2222417
loop_
_publ_author_name
'Yan, Yong'
'Mague, Joel T.'
'Donahue, James P.'
_publ_section_title
;
 A polymorph of tetraethylammonium chloride
;
_journal_coeditor_code           PK2163
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1491
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C8 H20 N + , Cl -'
_chemical_formula_moiety         'C8 H20 N + , Cl -'
_chemical_formula_sum            'C8 H20 Cl N'
_chemical_formula_weight         165.70
_chemical_melting_point          ?
_chemical_name_systematic
;
Tetraethylammonium chloride
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.378(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.429(2)
_cell_length_b                   8.109(2)
_cell_length_c                   14.499(4)
_cell_measurement_reflns_used    5930
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.46
_cell_measurement_theta_min      2.42
_cell_volume                     990.7(4)
_computing_cell_refinement       'SAINT (Bruker 2008)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008b)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008b)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w'
_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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8314
_diffrn_reflns_theta_full        27.75
_diffrn_reflns_theta_max         27.75
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008a)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         2302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0298
_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/[\s^2^(Fo^2^)+(0.0437P)^2^+0.2706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0828
_reflns_number_gt                2038
_reflns_number_total             2302
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    pk2163.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2222417
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_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
Cl Cl1 0.24449(3) 0.49267(3) 0.660880(18) 0.02030(10) Uani d . 1
N N1 0.25555(10) 0.10663(10) 0.86208(6) 0.01401(19) Uani d . 1
C C1 0.30638(13) 0.09217(13) 0.76286(7) 0.0177(2) Uani d . 1
H H1A 0.4027 0.0225 0.7610 0.021 Uiso calc R 1
H H1B 0.3350 0.2032 0.7402 0.021 Uiso calc R 1
C C2 0.18066(15) 0.01931(15) 0.69818(8) 0.0252(3) Uani d . 1
H H2A 0.1584 -0.0945 0.7166 0.038 Uiso calc R 1
H H2B 0.2191 0.0203 0.6349 0.038 Uiso calc R 1
H H2C 0.0833 0.0850 0.7012 0.038 Uiso calc R 1
C C3 0.19934(13) -0.05808(13) 0.90007(8) 0.0182(2) Uani d . 1
H H3A 0.1879 -0.0473 0.9676 0.022 Uiso calc R 1
H H3B 0.0930 -0.0825 0.8730 0.022 Uiso calc R 1
C C4 0.30819(14) -0.20341(14) 0.88139(8) 0.0232(2) Uani d . 1
H H4A 0.3011 -0.2321 0.8157 0.035 Uiso calc R 1
H H4B 0.2758 -0.2983 0.9183 0.035 Uiso calc R 1
H H4C 0.4178 -0.1735 0.8981 0.035 Uiso calc R 1
C C5 0.11843(12) 0.22872(13) 0.86575(7) 0.0176(2) Uani d . 1
H H5A 0.1432 0.3248 0.8265 0.021 Uiso calc R 1
H H5B 0.0218 0.1756 0.8393 0.021 Uiso calc R 1
C C6 0.08328(14) 0.28976(15) 0.96222(8) 0.0251(3) Uani d . 1
H H6A 0.0840 0.1963 1.0051 0.038 Uiso calc R 1
H H6B -0.0213 0.3426 0.9619 0.038 Uiso calc R 1
H H6C 0.1644 0.3697 0.9819 0.038 Uiso calc R 1
C C7 0.39616(12) 0.16349(13) 0.92106(7) 0.0167(2) Uani d . 1
H H7A 0.4806 0.0789 0.9185 0.020 Uiso calc R 1
H H7B 0.3629 0.1720 0.9859 0.020 Uiso calc R 1
C C8 0.46431(14) 0.32803(14) 0.89185(8) 0.0243(3) Uani d . 1
H H8A 0.5208 0.3142 0.8340 0.036 Uiso calc R 1
H H8B 0.5382 0.3684 0.9400 0.036 Uiso calc R 1
H H8C 0.3780 0.4078 0.8827 0.036 Uiso calc R 1
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
Cl1 0.01788(16) 0.02294(16) 0.02008(16) -0.00039(9) 0.00052(11) 0.00271(9)
N1 0.0142(4) 0.0146(4) 0.0132(4) 0.0006(3) 0.0001(3) 0.0003(3)
C1 0.0206(5) 0.0200(5) 0.0125(5) 0.0022(4) 0.0023(4) -0.0006(4)
C2 0.0280(6) 0.0301(6) 0.0174(6) 0.0023(5) -0.0054(5) -0.0035(4)
C3 0.0202(5) 0.0158(5) 0.0185(5) -0.0023(4) 0.0002(4) 0.0027(4)
C4 0.0281(6) 0.0158(5) 0.0256(6) 0.0021(4) -0.0023(5) 0.0008(4)
C5 0.0158(5) 0.0183(5) 0.0187(5) 0.0045(4) 0.0008(4) 0.0006(4)
C6 0.0265(6) 0.0276(6) 0.0214(6) 0.0090(5) 0.0053(4) -0.0007(4)
C7 0.0164(5) 0.0182(5) 0.0153(5) -0.0009(4) -0.0029(4) -0.0002(4)
C8 0.0249(6) 0.0224(6) 0.0253(6) -0.0062(5) -0.0035(5) 0.0013(4)
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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C7 108.90(8)
C1 N1 C5 108.39(8)
C7 N1 C5 111.46(8)
C1 N1 C3 111.88(8)
C7 N1 C3 107.94(8)
C5 N1 C3 108.30(8)
N1 C1 C2 114.05(9)
N1 C1 H1A 108.7
C2 C1 H1A 108.7
N1 C1 H1B 108.7
C2 C1 H1B 108.7
H1A C1 H1B 107.6
C1 C2 H2A 109.5
C1 C2 H2B 109.5
H2A C2 H2B 109.5
C1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
C4 C3 N1 114.85(9)
C4 C3 H3A 108.6
N1 C3 H3A 108.6
C4 C3 H3B 108.6
N1 C3 H3B 108.6
H3A C3 H3B 107.5
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C6 C5 N1 114.12(9)
C6 C5 H5A 108.7
N1 C5 H5A 108.7
C6 C5 H5B 108.7
N1 C5 H5B 108.7
H5A C5 H5B 107.6
C5 C6 H6A 109.5
C5 C6 H6B 109.5
H6A C6 H6B 109.5
C5 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N1 C7 C8 113.96(8)
N1 C7 H7A 108.8
C8 C7 H7A 108.8
N1 C7 H7B 108.8
C8 C7 H7B 108.8
H7A C7 H7B 107.7
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.5153(13)
N1 C7 1.5165(13)
N1 C5 1.5238(13)
N1 C3 1.5246(13)
C1 C2 1.5178(16)
C1 H1A 0.9900
C1 H1B 0.9900
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C3 C4 1.5219(15)
C3 H3A 0.9900
C3 H3B 0.9900
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C5 C6 1.5197(16)
C5 H5A 0.9900
C5 H5B 0.9900
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 C8 1.5170(15)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
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
C7 N1 C1 C2 174.07(9)
C5 N1 C1 C2 -64.51(11)
C3 N1 C1 C2 54.83(11)
C1 N1 C3 C4 47.32(11)
C7 N1 C3 C4 -72.47(11)
C5 N1 C3 C4 166.71(9)
C1 N1 C5 C6 -164.83(9)
C7 N1 C5 C6 -45.00(12)
C3 N1 C5 C6 73.60(11)
C1 N1 C7 C8 58.94(11)
C5 N1 C7 C8 -60.59(11)
C3 N1 C7 C8 -179.40(9)