#------------------------------------------------------------------------------
#$Date: 2019-10-02 09:33:18 +0300 (Wed, 02 Oct 2019) $
#$Revision: 219001 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/42/7234280.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_7234280
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                98.742(4)
_cell_angle_beta                 100.488(3)
_cell_angle_gamma                100.213(3)
_cell_formula_units_Z            4
_cell_length_a                   9.6337(3)
_cell_length_b                   10.7137(5)
_cell_length_c                   18.8281(9)
_cell_measurement_temperature    100(2)
_cell_volume                     1846.15(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11710
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         4.27
_exptl_absorpt_coefficient_mu    4.502
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             744
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         6426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0493
_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)+(0.0797P)²+0.4526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1375
_reflns_number_gt                5432
_reflns_number_total             6426
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2015-3-6053.cif
_cod_data_source_block           ad-10
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7234280
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
Cl1 Cl 0.53631(6) 0.38339(6) 0.62531(4) 0.03193(17) Uani 1 1 d . . .
Cl6 Cl 0.09827(7) 0.81934(7) 0.86048(4) 0.03901(19) Uani 1 1 d . . .
Cl2 Cl 0.29904(8) 0.42762(6) 0.52400(4) 0.0418(2) Uani 1 1 d . . .
Cl3 Cl 0.26368(8) 0.37877(7) 0.66717(4) 0.0435(2) Uani 1 1 d . . .
Cl5 Cl 0.38823(8) 0.86275(7) 0.94636(4) 0.0435(2) Uani 1 1 d . . .
Cl4 Cl 0.31148(8) 0.71130(8) 0.79872(4) 0.0455(2) Uani 1 1 d . . .
O1 O 0.38280(17) 0.12109(15) 0.57060(10) 0.0256(4) Uani 1 1 d . . .
O4 O 0.11578(19) 0.62080(18) 0.94910(11) 0.0345(4) Uani 1 1 d . . .
N1 N 0.2507(2) 0.86728(18) 0.53294(10) 0.0185(4) Uani 1 1 d . . .
H1 H 0.2900 0.9553 0.5411 0.022 Uiso 1 1 calc R . .
N2 N 0.21662(19) 0.34125(18) 0.96401(11) 0.0193(4) Uani 1 1 d . . .
H2 H 0.2464 0.4198 0.9503 0.023 Uiso 1 1 calc R . .
C2 C 0.4612(2) 0.8378(2) 0.62557(13) 0.0225(5) Uani 1 1 d . . .
H2A H 0.3976 0.8119 0.6589 0.027 Uiso 1 1 calc R . .
H2B H 0.4963 0.9327 0.6387 0.027 Uiso 1 1 calc R . .
O2 O 0.16499(19) 0.15606(18) 0.52780(13) 0.0404(5) Uani 1 1 d . . .
C25 C -0.1604(2) 0.1147(2) 0.89533(13) 0.0224(5) Uani 1 1 d . . .
H25A H -0.1697 0.1154 0.8422 0.027 Uiso 1 1 calc R . .
H25B H -0.2136 0.1778 0.9155 0.027 Uiso 1 1 calc R . .
C6 C 0.2524(3) 0.8864(3) 0.40162(13) 0.0246(5) Uani 1 1 d . . .
H6A H 0.3425 0.8535 0.4037 0.030 Uiso 1 1 calc R . .
H6B H 0.2793 0.9816 0.4170 0.030 Uiso 1 1 calc R . .
O3 O 0.3005(2) 0.55367(18) 0.91086(12) 0.0374(5) Uani 1 1 d . . .
C5 C 0.1691(2) 0.8299(2) 0.45455(13) 0.0217(5) Uani 1 1 d . . .
H5A H 0.0768 0.8597 0.4505 0.026 Uiso 1 1 calc R . .
H5B H 0.1457 0.7346 0.4401 0.026 Uiso 1 1 calc R . .
C13 C 0.3462(3) 0.3375(2) 0.59235(13) 0.0230(5) Uani 1 1 d . . .
C28 C 0.2154(2) 0.6272(2) 0.91706(13) 0.0209(5) Uani 1 1 d . . .
C21 C 0.3547(3) 0.5020(3) 1.16897(14) 0.0279(5) Uani 1 1 d . . .
H21A H 0.3483 0.4205 1.1881 0.033 Uiso 1 1 calc R . .
H21B H 0.4478 0.5600 1.1950 0.033 Uiso 1 1 calc R . .
C4 C 0.6713(3) 0.8014(3) 0.71559(14) 0.0321(6) Uani 1 1 d . . .
H4A H 0.7075 0.8949 0.7313 0.048 Uiso 1 1 calc R . .
H4B H 0.7527 0.7577 0.7203 0.048 Uiso 1 1 calc R . .
H4C H 0.6062 0.7708 0.7466 0.048 Uiso 1 1 calc R . .
C24 C -0.0015(2) 0.1551(2) 0.93379(13) 0.0202(5) Uani 1 1 d . . .
H24A H 0.0080 0.1567 0.9872 0.024 Uiso 1 1 calc R . .
H24B H 0.0517 0.0913 0.9144 0.024 Uiso 1 1 calc R . .
C14 C 0.2922(2) 0.1885(2) 0.56014(13) 0.0209(5) Uani 1 1 d . . .
C15 C 0.3220(2) 0.2600(2) 0.94643(13) 0.0202(5) Uani 1 1 d . . .
H15A H 0.2982 0.1775 0.9636 0.024 Uiso 1 1 calc R . .
H15B H 0.4201 0.3053 0.9740 0.024 Uiso 1 1 calc R . .
C11 C -0.0169(3) 0.7013(2) 0.63804(14) 0.0249(5) Uani 1 1 d . . .
H11A H 0.0299 0.7553 0.6869 0.030 Uiso 1 1 calc R . .
H11B H -0.1005 0.7367 0.6175 0.030 Uiso 1 1 calc R . .
C26 C -0.2276(3) -0.0201(3) 0.90539(15) 0.0283(6) Uani 1 1 d . . .
H26A H -0.1776 -0.0833 0.8837 0.042 Uiso 1 1 calc R . .
H26B H -0.3300 -0.0421 0.8810 0.042 Uiso 1 1 calc R . .
H26C H -0.2181 -0.0212 0.9580 0.042 Uiso 1 1 calc R . .
C23 C 0.0640(2) 0.2883(2) 0.92160(13) 0.0196(5) Uani 1 1 d . . .
H23A H 0.0620 0.2836 0.8685 0.024 Uiso 1 1 calc R . .
H23B H 0.0032 0.3492 0.9358 0.024 Uiso 1 1 calc R . .
C17 C 0.4471(3) 0.1637(2) 0.85319(13) 0.0241(5) Uani 1 1 d . . .
H17A H 0.5400 0.2239 0.8771 0.029 Uiso 1 1 calc R . .
H17B H 0.4405 0.0876 0.8773 0.029 Uiso 1 1 calc R . .
C1 C 0.3756(2) 0.8012(2) 0.54657(13) 0.0200(5) Uani 1 1 d . . .
H1A H 0.4409 0.8239 0.5134 0.024 Uiso 1 1 calc R . .
H1B H 0.3386 0.7066 0.5343 0.024 Uiso 1 1 calc R . .
C9 C 0.1497(2) 0.8491(2) 0.58509(13) 0.0206(5) Uani 1 1 d . . .
H9A H 0.0676 0.8905 0.5704 0.025 Uiso 1 1 calc R . .
H9B H 0.2017 0.8943 0.6353 0.025 Uiso 1 1 calc R . .
C19 C 0.2225(2) 0.3715(2) 1.04548(13) 0.0222(5) Uani 1 1 d . . .
H19A H 0.1345 0.4022 1.0535 0.027 Uiso 1 1 calc R . .
H19B H 0.2231 0.2914 1.0656 0.027 Uiso 1 1 calc R . .
C22 C 0.2318(3) 0.5651(3) 1.18641(14) 0.0307(6) Uani 1 1 d . . .
H22A H 0.2363 0.6453 1.1670 0.046 Uiso 1 1 calc R . .
H22B H 0.2410 0.5847 1.2398 0.046 Uiso 1 1 calc R . .
H22C H 0.1391 0.5060 1.1636 0.046 Uiso 1 1 calc R . .
C10 C 0.0905(3) 0.7091(2) 0.58749(14) 0.0232(5) Uani 1 1 d . . .
H10A H 0.1709 0.6681 0.6058 0.028 Uiso 1 1 calc R . .
H10B H 0.0418 0.6616 0.5373 0.028 Uiso 1 1 calc R . .
C16 C 0.3235(3) 0.2304(2) 0.86500(13) 0.0236(5) Uani 1 1 d . . .
H16A H 0.3351 0.3117 0.8457 0.028 Uiso 1 1 calc R . .
H16B H 0.2305 0.1738 0.8377 0.028 Uiso 1 1 calc R . .
C3 C 0.5898(3) 0.7719(2) 0.63582(14) 0.0259(5) Uani 1 1 d . . .
H3A H 0.5551 0.6773 0.6197 0.031 Uiso 1 1 calc R . .
H3B H 0.6562 0.8018 0.6045 0.031 Uiso 1 1 calc R . .
C20 C 0.3534(3) 0.4723(3) 1.08636(14) 0.0286(6) Uani 1 1 d . . .
H20A H 0.3537 0.5524 1.0661 0.034 Uiso 1 1 calc R . .
H20B H 0.4417 0.4414 1.0793 0.034 Uiso 1 1 calc R . .
C7 C 0.1635(3) 0.8513(3) 0.32277(14) 0.0303(6) Uani 1 1 d . . .
H7A H 0.2274 0.8748 0.2891 0.036 Uiso 1 1 calc R . .
H7B H 0.1267 0.7566 0.3101 0.036 Uiso 1 1 calc R . .
C18 C 0.4464(3) 0.1202(3) 0.77276(16) 0.0394(7) Uani 1 1 d . . .
H18A H 0.3555 0.0593 0.7488 0.059 Uiso 1 1 calc R . .
H18B H 0.5275 0.0778 0.7686 0.059 Uiso 1 1 calc R . .
H18C H 0.4558 0.1953 0.7488 0.059 Uiso 1 1 calc R . .
C27 C 0.2499(2) 0.7486(2) 0.88049(13) 0.0228(5) Uani 1 1 d . . .
C8 C 0.0364(3) 0.9177(3) 0.31024(15) 0.0350(6) Uani 1 1 d . . .
H8A H -0.0328 0.8879 0.3395 0.052 Uiso 1 1 calc R . .
H8B H -0.0110 0.8965 0.2580 0.052 Uiso 1 1 calc R . .
H8C H 0.0711 1.0114 0.3252 0.052 Uiso 1 1 calc R . .
C12 C -0.0706(3) 0.5633(3) 0.64717(16) 0.0346(6) Uani 1 1 d . . .
H12A H -0.1120 0.5083 0.5987 0.052 Uiso 1 1 calc R . .
H12B H -0.1446 0.5619 0.6767 0.052 Uiso 1 1 calc R . .
H12C H 0.0103 0.5308 0.6720 0.052 Uiso 1 1 calc R . .
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'
N N 0.0311 0.0180 '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'
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
C5 N1 C1 111.89(17) . .
C5 N1 C9 110.84(17) . .
C1 N1 C9 113.83(17) . .
C15 N2 C23 114.50(18) . .
C15 N2 C19 111.90(17) . .
C23 N2 C19 110.99(17) . .
C1 C2 C3 111.05(19) . .
C24 C25 C26 111.64(19) . .
C5 C6 C7 111.5(2) . .
N1 C5 C6 112.93(19) . .
C14 C13 Cl2 110.18(16) . .
C14 C13 Cl3 108.82(16) . .
Cl2 C13 Cl3 109.43(13) . .
C14 C13 Cl1 113.00(15) . .
Cl2 C13 Cl1 107.52(13) . .
Cl3 C13 Cl1 107.82(13) . .
O4 C28 O3 129.6(2) . .
O4 C28 C27 117.3(2) . .
O3 C28 C27 112.99(19) . .
C22 C21 C20 113.5(2) . .
C23 C24 C25 110.73(18) . .
O2 C14 O1 129.2(2) . .
O2 C14 C13 114.8(2) . .
O1 C14 C13 116.1(2) . .
N2 C15 C16 113.88(18) . .
C12 C11 C10 112.2(2) . .
N2 C23 C24 114.10(18) . .
C18 C17 C16 113.1(2) . .
N1 C1 C2 113.15(18) . .
N1 C9 C10 114.38(18) . .
C20 C19 N2 112.56(19) . .
C9 C10 C11 110.14(19) . .
C15 C16 C17 110.40(19) . .
C4 C3 C2 111.6(2) . .
C19 C20 C21 111.1(2) . .
C8 C7 C6 113.8(2) . .
C28 C27 Cl4 112.32(16) . .
C28 C27 Cl6 112.06(15) . .
Cl4 C27 Cl6 108.43(13) . .
C28 C27 Cl5 106.07(16) . .
Cl4 C27 Cl5 109.33(13) . .
Cl6 C27 Cl5 108.52(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C13 1.776(2) .
Cl6 C27 1.769(2) .
Cl2 C13 1.765(2) .
Cl3 C13 1.776(2) .
Cl5 C27 1.780(3) .
Cl4 C27 1.764(2) .
O1 C14 1.236(3) .
O4 C28 1.220(3) .
N1 C5 1.498(3) .
N1 C1 1.502(3) .
N1 C9 1.513(3) .
N2 C15 1.499(3) .
N2 C23 1.503(3) .
N2 C19 1.507(3) .
C2 C1 1.519(3) .
C2 C3 1.528(3) .
O2 C14 1.227(3) .
C25 C24 1.524(3) .
C25 C26 1.528(3) .
C6 C5 1.519(3) .
C6 C7 1.527(4) .
O3 C28 1.242(3) .
C13 C14 1.576(3) .
C28 C27 1.574(3) .
C21 C22 1.524(3) .
C21 C20 1.537(3) .
C4 C3 1.520(4) .
C24 C23 1.523(3) .
C15 C16 1.521(3) .
C11 C12 1.524(3) .
C11 C10 1.528(3) .
C17 C18 1.514(4) .
C17 C16 1.526(3) .
C9 C10 1.518(3) .
C19 C20 1.503(3) .
C7 C8 1.522(4) .
