#------------------------------------------------------------------------------
#$Date: 2019-12-18 16:43:10 +0100 (Wed 18 de Dec de 2019) $
#$Revision: 245325 $
#$URL: svn://www.crystallography.net/cod/cif/3/50/00/3500087.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_3500087
loop_
_publ_author_name
'Thierry Maris'
_publ_section_title
;
 Tetraethylammonium Bromide
;
_journal_name_full               'Personal communication to COD'
_journal_year                    2019
_chemical_formula_moiety         'C8 H20 N, Br'
_chemical_formula_sum            'C8 H20 Br N'
_chemical_formula_weight         210.16
_chemical_name_common            'Tetraethylammonium Bromide'
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_Hall           '-R 3 2"c'
_space_group_name_H-M_alt        'R -3 c :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   fmap
_audit_creation_date             2013-03-14
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   12.0127(2)
_cell_length_b                   12.0127(2)
_cell_length_c                   35.1627(8)
_cell_measurement_reflns_used    8728
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      72.903
_cell_measurement_theta_min      4.939
_cell_volume                     4394.34(14)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'Montel 200 Mirrors Optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            17958
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.089
_diffrn_reflns_theta_min         4.939
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    5.204
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_correction_T_min  0.5082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1468 before and 0.0613 after correction.
The Ratio of minimum to maximum transmission is 0.6743.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             1980
_exptl_crystal_recrystallization_method 'Recrystallized from EtOAc'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_special_details
;
 ?
;
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.00015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     50
_refine_ls_number_reflns         984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0262
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0444P)²+4.3537P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0743
_refine_special_details
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                920
_reflns_number_total             984
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL C2NBr in R-3c #167
CELL 1.54178 12.0127 12.0127 35.1627 90 90 120
ZERR 18 0.0002 0.0002 0.0008 0 0 0
LATT 3
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM -Y+X,-Y,0.5-Z
SYMM -X,-X+Y,0.5-Z
SYMM +Y,+X,0.5-Z

SFAC C H Br N
UNIT 144 360 18 18


L.S. 20
PLAN  3
SIZE 0.08 0.15 0.18
TEMP -123.15
REM reset to R-3c #167
BOND $H
CONF 
fmap 2
acta 
EXTI 0.000154
REM <HKL>E:\PROJETS\2013\C2NBr\OLEX2\C2NBr.hkl</HKL>
WGHT 0.0444 4.3537
FVAR 0.04796

Br1   3     0.00000  0.00000  0.00000  10.16667  0.02463  0.02463  0.02534 =
 -0.00000 -0.00000  0.01232 

Br2   3     0.66667  0.33333  0.01140  10.33333  0.02764  0.02764  0.02703 =
 -0.00000 -0.00000  0.01382 

C4    1     0.32667  0.32669  0.01066  11.00000  0.02768  0.03024  0.02199 =
 -0.00258 -0.00317  0.01442 
AFIX 137
H4a   2     0.26113  0.29586 -0.00935  11.00000 -1.50000 
H4b   2     0.36517  0.27154  0.01172  11.00000 -1.50000 
H4c   2     0.39353  0.41520  0.00506  11.00000 -1.50000 
AFIX 0
C3    1     0.26506  0.32276  0.04867  11.00000  0.02261  0.03303  0.02315 =
 -0.00163 -0.00418  0.01555 
AFIX 23
H3a   2     0.18214  0.24117  0.05037  11.00000 -1.20000 
H3b   2     0.24605  0.39397  0.04946  11.00000 -1.20000 
AFIX 0
C1    1     0.36317  0.21702  0.08643  11.00000  0.02900  0.02186  0.02498 =
 0.00055  0.00135  0.01489 
AFIX 23
H1a   2     0.41867  0.22844  0.10861  11.00000 -1.20000 
H1b   2     0.40817  0.21251  0.06340  11.00000 -1.20000 
AFIX 0
C2    1     0.23763  0.09042  0.09074  11.00000  0.04334  0.02133  0.03127 =
 0.00029  0.00279  0.00828 
AFIX 137
H2a   2     0.18571  0.07373  0.06771  11.00000 -1.50000 
H2b   2     0.19013  0.09547  0.11271  11.00000 -1.50000 
H2c   2     0.25622  0.02054  0.09459  11.00000 -1.50000 
AFIX 0
N1    4     0.34581  0.33333  0.08333  10.50000  0.01813  0.01986  0.01911 =
 -0.00080 -0.00040  0.00993 
HKLF 4
END
;
_cod_data_source_file            c2nbr.cif
_cod_data_source_block           c2nbr
_cod_depositor_comments
;Added Compound Name

 Added Title
;
_cod_original_cell_volume        4394.3(2)
_cod_original_sg_symbol_H-M      'R -3 c'
_cod_database_code               3500087
_cod_database_fobs_code          3500087
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H1A,H1B} of C1, {H3A,H3B} of C3
 At 1.5 times of:
  {H2A,H2B,H2C} of C2, {H4A,H4B,H4C} of C4
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C1(H1A,H1B)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C2(H2A,H2B,H2C)
;
_shelx_estimated_absorpt_t_max   0.681
_shelx_estimated_absorpt_t_min   0.454
_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           2012-9
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'y, x, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'y+2/3, x+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'y+1/3, x+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-y, -x, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-y+2/3, -x+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-y+1/3, -x+2/3, z+1/6'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.0000 0.0000 0.0000 0.02487(17) Uani 1 6 d S T P . .
Br2 Br 0.6667 0.3333 0.01140(2) 0.02744(17) Uani 1 3 d S T P . .
C4 C 0.32668(13) 0.32669(14) 0.01066(4) 0.0267(4) Uani 1 1 d . . . . .
H4A H 0.2611 0.2959 -0.0093 0.040 Uiso 1 1 calc R U . . .
H4B H 0.3652 0.2715 0.0117 0.040 Uiso 1 1 calc R U . . .
H4C H 0.3935 0.4152 0.0051 0.040 Uiso 1 1 calc R U . . .
C3 C 0.26506(13) 0.32276(14) 0.04867(4) 0.0255(3) Uani 1 1 d . . . . .
H3A H 0.1821 0.2412 0.0504 0.031 Uiso 1 1 calc R U . . .
H3B H 0.2460 0.3940 0.0495 0.031 Uiso 1 1 calc R U . . .
C1 C 0.36317(14) 0.21702(13) 0.08643(4) 0.0243(3) Uani 1 1 d . . . . .
H1A H 0.4187 0.2284 0.1086 0.029 Uiso 1 1 calc R U . . .
H1B H 0.4082 0.2125 0.0634 0.029 Uiso 1 1 calc R U . . .
C2 C 0.23763(17) 0.09042(15) 0.09074(5) 0.0355(4) Uani 1 1 d . . . . .
H2A H 0.1857 0.0737 0.0677 0.053 Uiso 1 1 calc R U . . .
H2B H 0.1901 0.0955 0.1127 0.053 Uiso 1 1 calc R U . . .
H2C H 0.2562 0.0205 0.0946 0.053 Uiso 1 1 calc R U . . .
N1 N 0.34581(12) 0.3333 0.0833 0.0188(3) Uani 1 2 d S T P . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0246(2) 0.0246(2) 0.0253(3) 0.000 0.000 0.01232(10)
Br2 0.02764(18) 0.02764(18) 0.0270(2) 0.000 0.000 0.01382(9)
C4 0.0277(8) 0.0302(8) 0.0220(7) -0.0026(6) -0.0032(6) 0.0144(6)
C3 0.0226(7) 0.0330(8) 0.0231(7) -0.0016(6) -0.0042(5) 0.0156(6)
C1 0.0290(7) 0.0219(7) 0.0250(7) 0.0005(6) 0.0014(6) 0.0149(6)
C2 0.0433(10) 0.0213(7) 0.0313(8) 0.0003(6) 0.0028(7) 0.0083(7)
N1 0.0181(6) 0.0199(8) 0.0191(8) -0.0008(6) -0.0004(3) 0.0099(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
H4A C4 H4B 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
C4 C3 H3A 108.5 . .
C4 C3 H3B 108.5 . .
C4 C3 N1 114.96(11) . .
H3A C3 H3B 107.5 . .
N1 C3 H3A 108.5 . .
N1 C3 H3B 108.5 . .
H1A C1 H1B 107.7 . .
C2 C1 H1A 108.8 . .
C2 C1 H1B 108.8 . .
N1 C1 H1A 108.8 . .
N1 C1 H1B 108.8 . .
N1 C1 C2 113.82(13) . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2B 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C3 N1 C3 106.94(14) . 16_554
C1 N1 C3 110.87(8) . 16_554
C1 N1 C3 110.86(8) 16_554 16_554
C1 N1 C3 110.85(8) . .
C1 N1 C3 110.86(8) 16_554 .
C1 N1 C1 106.51(14) . 16_554
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C4 C3 1.5170(19) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C3 N1 1.5231(15) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C1 C2 1.522(2) .
C1 N1 1.5163(16) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
N1 C3 1.5231(15) 16_554
N1 C1 1.5163(16) 16_554
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
C4 C3 N1 C3 173.29(15) . . . 16_554
C4 C3 N1 C1 -65.75(14) . . . .
C4 C3 N1 C1 52.33(15) . . . 16_554
C2 C1 N1 C3 -60.66(15) . . . .
C2 C1 N1 C3 57.95(15) . . . 16_554
C2 C1 N1 C1 178.65(15) . . . 16_554
