#------------------------------------------------------------------------------
#$Date: 2019-10-02 09:33:18 +0300 (Wed, 02 Oct 2019) $
#$Revision: 219001 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/42/7234281.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_7234281
loop_
_publ_author_name
'Muhammad Adnan Asghar'
'Chengmin Ji'
'Yuelan Zhou'
'Zhihua Sun'
'Tariq Khan'
'Shuquan Zhang'
'Sangen Zhao'
'Junhua Luo'
_publ_section_title
;
 Order-disorder phase transition coupled with torsion in
 tri-n-butylammonium trichloroacetate (TBAT)
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              6053
_journal_page_last               6057
_journal_paper_doi               10.1039/C5TC00989H
_journal_volume                  3
_journal_year                    2015
_chemical_formula_moiety         'C12 H28 N, C2 Cl3 O2'
_chemical_formula_sum            'C14 H28 Cl3 N O2'
_chemical_formula_weight         348.72
_chemical_melting_point          355
_chemical_name_systematic        'Tri-n-butylammonium Trichloroacetate '
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                98.677(4)
_cell_angle_beta                 101.665(4)
_cell_angle_gamma                98.350(3)
_cell_formula_units_Z            4
_cell_length_a                   9.6704(3)
_cell_length_b                   10.5407(4)
_cell_length_c                   19.7334(9)
_cell_measurement_temperature    220(2)
_cell_volume                     1915.04(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20199
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         4.31
_exptl_absorpt_coefficient_mu    4.340
_exptl_absorpt_correction_T_max  0.5621
_exptl_absorpt_correction_T_min  0.4100
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6738
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0643
_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)+(0.0805P)²+1.2971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1657
_refine_ls_wR_factor_ref         0.1813
_reflns_number_gt                5300
_reflns_number_total             6738
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2015-3-6053.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1915.04(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7234281
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl3 Cl 0.38614(12) 0.17657(11) 0.64502(6) 0.0934(4) Uani 1 1 d . . .
Cl1 Cl 0.09193(14) 0.12929(11) 0.57271(9) 0.1333(7) Uani 1 1 d . . .
Cl2 Cl 0.1921(2) 0.31942(19) 0.69918(7) 0.1379(7) Uani 1 1 d . . .
Cl5A Cl 0.0400(3) 0.3866(3) 0.1244(4) 0.0867(15) Uani 0.74(2) 1 d PU A 7
Cl4A Cl -0.2291(12) 0.4039(6) 0.1569(6) 0.1181(17) Uani 0.66(4) 1 d PU A 5
Cl6A Cl -0.1935(12) 0.4267(6) 0.0198(5) 0.101(2) Uani 0.61(3) 1 d PU A 9
O4 O 0.1655(2) 0.4208(2) 0.56618(13) 0.0630(6) Uani 1 1 d . . .
O11 O -0.1092(2) 0.12642(18) 0.06277(13) 0.0612(6) Uani 1 1 d . . .
C11 C 0.3673(3) 0.1394(3) 0.40139(19) 0.0614(8) Uani 1 1 d . . .
H11A H 0.3635 0.1365 0.3512 0.074 Uiso 1 1 calc R B 2
H11B H 0.3152 0.2073 0.4168 0.074 Uiso 1 1 calc R B 2
O7 O 0.3692(3) 0.3621(3) 0.55234(17) 0.0862(8) Uani 1 1 d . . .
N2 N 0.2377(3) 0.1308(2) -0.03377(12) 0.0504(6) Uani 1 1 d . C .
H2 H 0.2019 0.0432 -0.0390 0.061 Uiso 1 1 calc R . .
C24 C 0.0345(3) 0.1488(3) -0.13122(19) 0.0621(8) Uani 1 1 d . I .
H24A H 0.0057 0.0537 -0.1409 0.074 Uiso 1 1 calc R . .
H24B H 0.0989 0.1722 -0.1617 0.074 Uiso 1 1 calc R . .
N1 N 0.7480(3) 0.3488(2) 0.46991(13) 0.0524(6) Uani 1 1 d . F .
H1 H 0.7764 0.4309 0.4614 0.063 Uiso 1 1 calc R . .
C20A C 0.2512(5) 0.1113(5) 0.0915(2) 0.0584(15) Uani 0.665(9) 1 d PU C 1
H20A H 0.2480 0.0172 0.0788 0.070 Uiso 0.665(9) 1 calc PR C 1
H20B H 0.1529 0.1261 0.0894 0.070 Uiso 0.665(9) 1 calc PR C 1
C28 C -0.2020(3) 0.1938(3) 0.06240(16) 0.0475(6) Uani 1 1 d . A .
C25 C -0.0988(4) 0.2118(4) -0.1475(3) 0.0823(11) Uani 1 1 d . . .
H25A H -0.1644 0.1856 -0.1182 0.099 Uiso 1 1 calc R D 2
H25B H -0.0699 0.3070 -0.1357 0.099 Uiso 1 1 calc R D 2
C17 C 0.4051(4) 0.2792(3) -0.0838(2) 0.0625(8) Uani 1 1 d . . .
H17A H 0.3266 0.3217 -0.1035 0.075 Uiso 1 1 calc R . .
H17B H 0.4515 0.3287 -0.0365 0.075 Uiso 1 1 calc R . .
C27 C -0.1458(3) 0.3443(3) 0.09101(17) 0.0540(7) Uani 1 1 d . . .
C10 C 0.5226(3) 0.1752(3) 0.44198(17) 0.0545(7) Uani 1 1 d . H .
H10A H 0.5271 0.1751 0.4920 0.065 Uiso 1 1 calc R . .
H10B H 0.5760 0.1094 0.4252 0.065 Uiso 1 1 calc R . .
C9 C 0.5918(3) 0.3077(3) 0.43336(15) 0.0480(6) Uani 1 1 d . . .
H9A H 0.5823 0.3078 0.3830 0.058 Uiso 1 1 calc R H .
H9B H 0.5390 0.3728 0.4514 0.058 Uiso 1 1 calc R . .
C14 C 0.2619(3) 0.3564(3) 0.57553(15) 0.0461(6) Uani 1 1 d . . .
C18 C 0.3449(3) 0.1412(3) -0.07886(17) 0.0520(7) Uani 1 1 d . . .
H18A H 0.2991 0.0928 -0.1265 0.062 Uiso 1 1 calc R . .
H18B H 0.4246 0.0992 -0.0600 0.062 Uiso 1 1 calc R . .
O14 O -0.3308(3) 0.1612(2) 0.0403(2) 0.0980(10) Uani 1 1 d . . .
C13 C 0.2365(3) 0.2511(3) 0.62202(17) 0.0558(7) Uani 1 1 d . . .
C23 C 0.1120(3) 0.1942(3) -0.05552(18) 0.0577(8) Uani 1 1 d . . .
H23A H 0.1450 0.2888 -0.0472 0.069 Uiso 1 1 calc R I .
H23B H 0.0443 0.1769 -0.0257 0.069 Uiso 1 1 calc R . .
C19 C 0.3109(6) 0.1768(4) 0.0429(2) 0.0939(15) Uani 1 1 d . . .
H19A H 0.4122 0.1687 0.0492 0.113 Uiso 0.665(9) 1 d PR C 1
H19B H 0.3078 0.2698 0.0552 0.113 Uiso 0.665(9) 1 d PR C 1
H19C H 0.3900 0.2467 0.0436 0.113 Uiso 0.335(9) 1 d PR C 2
H19D H 0.2414 0.2185 0.0635 0.113 Uiso 0.335(9) 1 d PR C 2
C16 C 0.5128(4) 0.2808(4) -0.1295(2) 0.0723(9) Uani 1 1 d . . .
H16A H 0.4674 0.2266 -0.1758 0.087 Uiso 1 1 calc R . .
H16B H 0.5933 0.2421 -0.1082 0.087 Uiso 1 1 calc R . .
C4 C 0.8440(3) 0.2652(3) 0.4426(2) 0.0645(9) Uani 1 1 d . . .
H4A H 0.9435 0.3024 0.4673 0.077 Uiso 1 1 calc R H .
H4B H 0.8211 0.1784 0.4540 0.077 Uiso 1 1 calc R . .
C3 C 0.8341(4) 0.2505(4) 0.3664(2) 0.0772(10) Uani 1 1 d . G .
H3A H 0.8414 0.3367 0.3531 0.093 Uiso 1 1 calc R E 2
H3B H 0.7404 0.1987 0.3409 0.093 Uiso 1 1 calc R E 2
C5 C 0.7808(5) 0.3601(3) 0.54801(19) 0.0814(11) Uani 1 1 d U . .
H5A H 0.7466 0.2749 0.5588 0.098 Uiso 0.743(8) 1 d PR F 1
H5B H 0.8852 0.3803 0.5658 0.098 Uiso 0.743(8) 1 d PR F 1
H5C H 0.6896 0.3284 0.5595 0.098 Uiso 0.257(8) 1 d PR F 2
H5D H 0.8429 0.2969 0.5586 0.098 Uiso 0.257(8) 1 d PR F 2
C15 C 0.5702(5) 0.4173(5) -0.1392(3) 0.0986(15) Uani 1 1 d . . .
H15A H 0.4943 0.4503 -0.1676 0.148 Uiso 1 1 calc R . .
H15B H 0.6491 0.4145 -0.1625 0.148 Uiso 1 1 calc R . .
H15C H 0.6039 0.4744 -0.0935 0.148 Uiso 1 1 calc R . .
C21 C 0.3438(7) 0.1631(5) 0.1666(2) 0.1023(15) Uani 1 1 d . . .
H21A H 0.3714 0.2577 0.1712 0.123 Uiso 0.665(9) 1 d PR C 1
H21B H 0.2803 0.1491 0.1987 0.123 Uiso 0.665(9) 1 d PR C 1
H21C H 0.3497 0.2570 0.1810 0.123 Uiso 0.335(9) 1 d PR C 2
H21D H 0.2564 0.1150 0.1771 0.123 Uiso 0.335(9) 1 d PR C 2
C2 C 0.9534(5) 0.1834(5) 0.3450(3) 0.1039(16) Uani 1 1 d . G 2
H2A H 1.0457 0.2422 0.3652 0.125 Uiso 1 1 calc R G 2
H2B H 0.9557 0.1047 0.3658 0.125 Uiso 1 1 calc R G 2
C12 C 0.2935(4) 0.0087(4) 0.4115(2) 0.0810(11) Uani 1 1 d . H 2
H12A H 0.3420 -0.0595 0.3943 0.122 Uiso 1 1 calc R H 2
H12B H 0.1942 -0.0089 0.3855 0.122 Uiso 1 1 calc R H 2
H12C H 0.2972 0.0109 0.4612 0.122 Uiso 1 1 calc R H 2
C22 C 0.4743(6) 0.1137(7) 0.1941(3) 0.1171(18) Uani 1 1 d . C 2
H22A H 0.4699 0.0269 0.1682 0.141 Uiso 1 1 d R C 2
H22B H 0.4825 0.1105 0.2436 0.141 Uiso 1 1 d R C 2
H22C H 0.5572 0.1717 0.1887 0.141 Uiso 1 1 d R C 2
C26 C -0.1757(5) 0.1724(6) -0.2239(3) 0.1114(17) Uani 1 1 d . I 2
H26A H -0.1117 0.1999 -0.2531 0.167 Uiso 1 1 calc R I 2
H26B H -0.2594 0.2136 -0.2323 0.167 Uiso 1 1 calc R I 2
H26C H -0.2056 0.0784 -0.2356 0.167 Uiso 1 1 calc R I 2
C6A C 0.7196(5) 0.4543(4) 0.5846(2) 0.0588(12) Uani 0.743(8) 1 d PU F 1
H6A1 H 0.6148 0.4282 0.5727 0.071 Uiso 0.743(8) 1 calc PR F 1
H6A2 H 0.7436 0.5386 0.5706 0.071 Uiso 0.743(8) 1 calc PR F 1
C7 C 0.7783(7) 0.4677(5) 0.6661(2) 0.1026(14) Uani 1 1 d U . .
H7A H 0.7659 0.3817 0.6796 0.123 Uiso 0.743(8) 1 d PR F 1
H7B H 0.8806 0.5067 0.6799 0.123 Uiso 0.743(8) 1 d PR F 1
H7C H 0.7229 0.3789 0.6597 0.123 Uiso 0.257(8) 1 d PR F 2
H7D H 0.8656 0.4709 0.7020 0.123 Uiso 0.257(8) 1 d PR F 2
C8 C 0.6937(6) 0.5506(5) 0.7000(2) 0.1028(15) Uani 1 1 d . F .
H8A H 0.7191 0.6394 0.6930 0.154 Uiso 1 1 calc R . .
H8B H 0.7136 0.5491 0.7501 0.154 Uiso 1 1 calc R . .
H8C H 0.5924 0.5185 0.6795 0.154 Uiso 1 1 calc R . .
C1 C 0.9389(9) 0.1475(9) 0.2710(4) 0.179(4) Uani 1 1 d . . .
H1A H 0.8509 0.0847 0.2508 0.269 Uiso 1 1 calc R G 2
H1B H 1.0202 0.1088 0.2622 0.269 Uiso 1 1 calc R G 2
H1C H 0.9359 0.2244 0.2497 0.269 Uiso 1 1 calc R G 2
C6B C 0.8447(18) 0.4702(13) 0.5948(7) 0.068(3) Uani 0.257(8) 1 d PU F 2
H6B1 H 0.8253 0.5469 0.5745 0.081 Uiso 0.257(8) 1 calc PR F 2
H6B2 H 0.9488 0.4742 0.6070 0.081 Uiso 0.257(8) 1 calc PR F 2
C20B C 0.3600(11) 0.1155(10) 0.0845(5) 0.057(3) Uani 0.335(9) 1 d PU C 2
H20C H 0.4622 0.1200 0.0852 0.069 Uiso 0.335(9) 1 calc PR C 2
H20D H 0.3131 0.0239 0.0685 0.069 Uiso 0.335(9) 1 calc PR C 2
Cl6B Cl -0.131(3) 0.4170(8) 0.0190(8) 0.105(4) Uani 0.39(3) 1 d PU A 10
Cl5B Cl 0.018(2) 0.3682(13) 0.1529(11) 0.118(4) Uani 0.26(2) 1 d PU A 8
Cl4B Cl -0.268(3) 0.4082(8) 0.1327(19) 0.116(5) Uani 0.34(4) 1 d PU A 6
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C10 C11 C12 112.5(3) . .
C23 N2 C18 114.3(2) . .
C23 N2 C19 112.4(3) . .
C18 N2 C19 110.6(3) . .
C23 C24 C25 110.4(3) . .
C5 N1 C4 107.2(3) . .
C5 N1 C9 115.5(3) . .
C4 N1 C9 114.4(2) . .
C19 C20A C21 109.6(4) . .
O14 C28 O11 128.7(3) . .
O14 C28 C27 115.7(2) . .
O11 C28 C27 115.5(2) . .
C26 C25 C24 111.7(4) . .
C16 C17 C18 111.1(3) . .
C28 C27 Cl4B 109.4(5) . .
C28 C27 Cl6B 107.3(4) . .
Cl4B C27 Cl6B 109.9(13) . .
C28 C27 Cl4A 111.6(3) . .
Cl4B C27 Cl4A 18.4(11) . .
Cl6B C27 Cl4A 123.8(7) . .
C28 C27 Cl5B 109.8(4) . .
Cl4B C27 Cl5B 107.9(16) . .
Cl6B C27 Cl5B 112.6(14) . .
Cl4A C27 Cl5B 90.5(10) . .
C28 C27 Cl5A 114.3(2) . .
Cl4B C27 Cl5A 122.8(12) . .
Cl6B C27 Cl5A 90.6(9) . .
Cl4A C27 Cl5A 107.8(5) . .
Cl5B C27 Cl5A 22.6(8) . .
C28 C27 Cl6A 107.5(3) . .
Cl4B C27 Cl6A 91.1(13) . .
Cl6B C27 Cl6A 20.5(5) . .
Cl4A C27 Cl6A 107.0(7) . .
Cl5B C27 Cl6A 128.8(10) . .
Cl5A C27 Cl6A 108.4(5) . .
C9 C10 C11 111.5(2) . .
N1 C9 C10 115.0(2) . .
O7 C14 O4 128.7(3) . .
O7 C14 C13 117.3(3) . .
O4 C14 C13 113.9(2) . .
N2 C18 C17 114.6(2) . .
C14 C13 Cl2 110.8(2) . .
C14 C13 Cl3 113.1(2) . .
Cl2 C13 Cl3 108.46(18) . .
C14 C13 Cl1 107.5(2) . .
Cl2 C13 Cl1 108.85(19) . .
Cl3 C13 Cl1 108.10(18) . .
N2 C23 C24 114.0(2) . .
C20B C19 C20A 47.9(5) . .
C20B C19 N2 128.8(6) . .
C20A C19 N2 116.0(4) . .
C17 C16 C15 112.9(3) . .
C3 C4 N1 115.0(3) . .
C4 C3 C2 111.4(4) . .
C6B C5 C6A 50.1(7) . .
C6B C5 N1 125.0(6) . .
C6A C5 N1 115.4(3) . .
C22 C21 C20A 122.5(4) . .
C22 C21 C20B 90.2(5) . .
C20A C21 C20B 39.2(4) . .
C1 C2 C3 114.9(5) . .
C5 C6A C7 109.8(4) . .
C8 C7 C6A 106.3(4) . .
C8 C7 C6B 133.1(6) . .
C6A C7 C6B 42.2(6) . .
C5 C6B C7 107.8(10) . .
C19 C20B C21 115.4(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl3 C13 1.757(3) .
Cl1 C13 1.761(3) .
Cl2 C13 1.745(3) .
Cl5A C27 1.750(4) .
Cl4A C27 1.749(7) .
Cl6A C27 1.780(7) .
O4 C14 1.231(3) .
O11 C28 1.221(3) .
C11 C10 1.515(4) .
C11 C12 1.518(5) .
O7 C14 1.213(3) .
N2 C23 1.490(4) .
N2 C18 1.499(4) .
N2 C19 1.507(4) .
C24 C23 1.500(5) .
C24 C25 1.533(5) .
N1 C5 1.492(4) .
N1 C4 1.492(4) .
N1 C9 1.504(4) .
C20A C19 1.427(6) .
C20A C21 1.541(6) .
C28 O14 1.213(4) .
C28 C27 1.577(4) .
C25 C26 1.505(7) .
C17 C16 1.510(5) .
C17 C18 1.511(4) .
C27 Cl4B 1.724(11) .
C27 Cl6B 1.733(11) .
C27 Cl5B 1.750(11) .
C10 C9 1.508(4) .
C14 C13 1.567(4) .
C19 C20B 1.188(11) .
C16 C15 1.520(5) .
C4 C3 1.470(5) .
C3 C2 1.533(5) .
C5 C6B 1.348(14) .
C5 C6A 1.409(6) .
C21 C22 1.469(7) .
C21 C20B 1.666(10) .
C2 C1 1.425(9) .
C6A C7 1.572(6) .
C7 C8 1.460(7) .
C7 C6B 1.664(14) .
