#------------------------------------------------------------------------------
#$Date: 2016-10-22 04:02:13 +0300 (Sat, 22 Oct 2016) $
#$Revision: 187490 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/18/2241891.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_2241891
loop_
_publ_author_name
'Averkiev, Boris B.'
'Valencia, Bianca C.'
'Getmanenko, Yulia A.'
'Timofeeva, Tatiana V.'
_publ_section_title
;
 Crystal structure of N,N,N-triethylhydroxylammonium
 chloride
;
_journal_coeditor_code           HB7617
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1607
_journal_page_last               1609
_journal_paper_doi               10.1107/S2056989016016169
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C6 H16 N O +, Cl -'
_chemical_formula_moiety         'C6 H16 N O +, Cl -'
_chemical_formula_sum            'C6 H16 Cl N O'
_chemical_formula_weight         153.65
_chemical_name_systematic
;
N,N,N-Triethylhydroxylammonium chloride
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.816(5)
_cell_length_b                   6.371(3)
_cell_length_c                   10.439(4)
_cell_measurement_reflns_used    2230
_cell_measurement_temperature    215(2)
_cell_measurement_theta_max      32.34
_cell_measurement_theta_min      3.57
_cell_volume                     852.4(6)
_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
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      215(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12103
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         3.2
_exptl_absorpt_coefficient_mu    0.380
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.140
_refine_ls_abs_structure_details
;
Flack x determined using 1146 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   0.046(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0206
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0429P)²+0.0129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0563
_reflns_number_gt                2447
_reflns_number_total             2484
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7617sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        852.3(6)
_cod_database_code               2241891
_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.
;
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'
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
Cl Cl1 0.35543(2) -0.08505(4) 0.50629(5) 0.03438(9) Uani d 1
O O1 0.47318(6) 0.30749(12) 0.48070(7) 0.02789(17) Uani d 1
H H1 0.4399(16) 0.188(4) 0.484(3) 0.060(6) Uiso d 1
N N1 0.53046(7) 0.29675(12) 0.36425(9) 0.02182(16) Uani d 1
C C1 0.45457(9) 0.28944(18) 0.25337(10) 0.0299(2) Uani d 1
H H1B 0.4138(19) 0.155(4) 0.269(2) 0.054(5) Uiso d 1
H H1A 0.4948(15) 0.269(3) 0.1798(16) 0.031(4) Uiso d 1
C C2 0.59511(9) 0.49467(16) 0.36668(10) 0.0269(2) Uani d 1
H H2B 0.5464(16) 0.599(3) 0.380(2) 0.038(5) Uiso d 1
H H2A 0.6374(13) 0.486(3) 0.4418(18) 0.028(4) Uiso d 1
C C3 0.59581(10) 0.09863(15) 0.36273(11) 0.0278(2) Uani d 1
H H3B 0.5446(14) -0.015(3) 0.358(2) 0.038(4) Uiso d 1
H H3A 0.6338(13) 0.106(3) 0.287(2) 0.030(4) Uiso d 1
C C4 0.38747(11) 0.4836(3) 0.24189(13) 0.0404(3) Uani d 1
H H4C 0.3582(16) 0.529(4) 0.320(2) 0.049(6) Uiso d 1
H H4B 0.4278(16) 0.602(3) 0.207(2) 0.040(5) Uiso d 1
H H4A 0.328(3) 0.450(5) 0.181(4) 0.086(10) Uiso d 1
C C5 0.66019(11) 0.5267(2) 0.24769(13) 0.0347(2) Uani d 1
H H5C 0.712(2) 0.420(4) 0.240(3) 0.077(8) Uiso d 1
H H5B 0.616(2) 0.543(4) 0.173(3) 0.064(7) Uiso d 1
H H5A 0.6950(19) 0.650(4) 0.252(2) 0.060(6) Uiso d 1
C C6 0.66688(14) 0.0771(2) 0.47737(14) 0.0392(3) Uani d 1
H H6C 0.7011(19) -0.051(4) 0.471(2) 0.054(6) Uiso d 1
H H6B 0.7175(18) 0.182(4) 0.478(3) 0.066(7) Uiso d 1
H H6A 0.6251(18) 0.078(3) 0.562(3) 0.044(6) Uiso d 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'
O O 0.0106 0.0060 '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
N1 O1 H1 104.2(17)
O1 N1 C2 103.23(7)
O1 N1 C1 108.89(8)
C2 N1 C1 113.06(8)
O1 N1 C3 109.55(8)
C2 N1 C3 113.13(8)
C1 N1 C3 108.77(8)
C4 C1 N1 113.66(10)
C4 C1 H1B 114.1(13)
N1 C1 H1B 103.7(14)
C4 C1 H1A 111.2(12)
N1 C1 H1A 106.2(12)
H1B C1 H1A 107.3(17)
N1 C2 C5 113.73(9)
N1 C2 H2B 103.4(11)
C5 C2 H2B 113.7(12)
N1 C2 H2A 106.1(12)
C5 C2 H2A 111.7(10)
H2B C2 H2A 107.5(17)
C6 C3 N1 113.62(9)
C6 C3 H3B 112.2(12)
N1 C3 H3B 104.2(11)
C6 C3 H3A 111.4(11)
N1 C3 H3A 104.8(11)
H3B C3 H3A 110.2(16)
C1 C4 H4C 114.1(16)
C1 C4 H4B 111.0(11)
H4C C4 H4B 107(2)
C1 C4 H4A 107.6(18)
H4C C4 H4A 108(3)
H4B C4 H4A 109(2)
C2 C5 H5C 111(2)
C2 C5 H5B 110.9(18)
H5C C5 H5B 115(3)
C2 C5 H5A 110.5(16)
H5C C5 H5A 106(2)
H5B C5 H5A 103(2)
C3 C6 H6C 107.9(16)
C3 C6 H6B 111.1(16)
H6C C6 H6B 108(2)
C3 C6 H6A 111.4(14)
H6C C6 H6A 108.0(19)
H6B C6 H6A 111(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O1 1.4218(11)
O1 H1 0.87(2)
N1 C2 1.5090(13)
N1 C1 1.5126(14)
N1 C3 1.5148(13)
C1 C4 1.5113(19)
C1 H1B 1.01(2)
C1 H1A 0.934(18)
C2 C5 1.5101(18)
C2 H2B 0.921(19)
C2 H2A 0.955(18)
C3 C6 1.5103(19)
C3 H3B 0.977(19)
C3 H3A 0.93(2)
C4 H4C 0.94(3)
C4 H4B 0.987(19)
C4 H4A 1.02(4)
C5 H5C 0.96(3)
C5 H5B 0.97(3)
C5 H5A 0.91(3)
C6 H6C 0.93(2)
C6 H6B 0.93(2)
C6 H6A 1.03(3)
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
O1 H1 Cl1 . 0.87(2) 2.06(2) 2.9330(12) 175(2)
C1 H1A Cl1 2_654 0.934(18) 2.888(19) 3.7786(15) 159.8(15)
C2 H2A Cl1 3 0.955(18) 2.943(17) 3.6859(16) 135.6(14)
C3 H3B Cl1 . 0.977(19) 2.911(19) 3.6203(16) 130.3(14)
C3 H3A Cl1 2_654 0.93(2) 2.93(2) 3.7740(19) 150.7(14)
C4 H4A Cl1 4_554 1.02(4) 2.98(4) 3.9913(18) 172(2)
C5 H5B O1 2_664 0.97(3) 2.50(3) 3.4359(18) 163(2)
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
O1 N1 C1 C4 62.86(11)
C2 N1 C1 C4 -51.26(13)
C3 N1 C1 C4 -177.82(10)
O1 N1 C2 C5 -176.96(9)
C1 N1 C2 C5 -59.47(12)
C3 N1 C2 C5 64.73(12)
O1 N1 C3 C6 -54.95(13)
C2 N1 C3 C6 59.62(13)
C1 N1 C3 C6 -173.87(10)

_cod_database_fobs_code 2241891
