#------------------------------------------------------------------------------
#$Date: 2016-08-07 10:23:58 +0200 (dom 07 de ago de 2016) $
#$Revision: 185234 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/46/7224665.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_7224665
loop_
_publ_author_name
'Zeng, Siyuan'
'Sun, Zhihua'
'Ji, Chengmin'
'Zhang, Shuquan'
'Song, Cheng'
'Luo, Junhua'
_publ_section_title
;
 Dibenzylammonium trichloroacetate: an above-room-temperature
 order--disorder switchable dielectric material
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              3606
_journal_paper_doi               10.1039/C6CE00194G
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C14 H16 N, C2 Cl3 O2'
_chemical_formula_sum            'C24 H24 Cl4.5 N1.5 O3'
_chemical_formula_weight         540.97
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-05-14 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.9771(10)
_cell_length_b                   17.8261(7)
_cell_length_c                   10.0751(3)
_cell_measurement_temperature    293(2)
_cell_volume                     5024.7(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16412
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_T_max  0.871
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
_exptl_special_details 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2232
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0400
_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)+(0.0420P)²+2.6301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                4048
_reflns_number_total             5280
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce00194g2.cif
_cod_data_source_block           f:\zsy\supern~1\rt\olex2_~1\401-rt
_cod_depositor_comments
'Adding full bibliography for 7224662--7224665.cif.'
_cod_original_formula_sum        'C24 H24 Cl4.50 N1.50 O3'
_cod_database_code               7224665
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, 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
Cl1 Cl 0.27901(3) 0.2500 0.30351(7) 0.0445(2) Uani 1 2 d S
Cl5 Cl 0.59883(3) 0.2500 0.35453(8) 0.0500(2) Uani 1 2 d S
Cl6 Cl 0.68560(2) 0.33041(3) 0.40260(6) 0.04996(16) Uani 1 1 d .
Cl4 Cl 0.55011(3) 0.2500 0.90916(9) 0.0696(3) Uani 1 2 d S
Cl2 Cl 0.36631(3) 0.33032(4) 0.33974(7) 0.0728(2) Uani 1 1 d .
Cl3 Cl 0.50991(3) 0.33045(4) 1.12799(7) 0.0660(2) Uani 1 1 d .
O4 O 0.45242(6) 0.2500 0.83846(18) 0.0368(5) Uani 1 2 d S
O1 O 0.28816(7) 0.2500 0.5890(2) 0.0449(5) Uani 1 2 d S
O2 O 0.36726(7) 0.2500 0.60311(18) 0.0407(5) Uani 1 2 d S
O3 O 0.41981(7) 0.2500 1.03883(19) 0.0460(5) Uani 1 2 d S
O6 O 0.68217(7) 0.2500 0.66413(18) 0.0410(5) Uani 1 2 d S
O5 O 0.60318(7) 0.2500 0.6427(2) 0.0472(6) Uani 1 2 d S
N3 N 0.69099(7) 0.2500 0.9316(2) 0.0279(5) Uani 1 2 d S
H3A H 0.7230 0.2500 0.9401 0.033 Uiso 1 2 calc SR
H3B H 0.6840 0.2500 0.8444 0.033 Uiso 1 2 calc SR
N1 N 0.65862(7) 0.7500 0.1269(2) 0.0289(5) Uani 1 2 d S
H1A H 0.6505 0.7500 0.2133 0.035 Uiso 1 2 calc SR
H1B H 0.6315 0.7500 0.0788 0.035 Uiso 1 2 calc SR
N2 N 0.50260(8) 0.2500 0.6048(2) 0.0288(5) Uani 1 2 d S
H2A H 0.5347 0.2500 0.6003 0.035 Uiso 1 2 calc SR
H2B H 0.4944 0.2500 0.6912 0.035 Uiso 1 2 calc SR
C27 C 0.65225(9) 0.2500 0.4476(3) 0.0264(5) Uani 1 2 d S
C23 C 0.33429(9) 0.2500 0.3885(3) 0.0283(6) Uani 1 2 d S
C26 C 0.64434(9) 0.2500 0.6018(2) 0.0262(5) Uani 1 2 d S
C24 C 0.45338(9) 0.2500 0.9602(3) 0.0268(6) Uani 1 2 d S
C22 C 0.32902(9) 0.2500 0.5436(3) 0.0279(6) Uani 1 2 d S
C25 C 0.50419(10) 0.2500 1.0276(3) 0.0335(6) Uani 1 2 d S
C16 C 0.68954(6) 0.39044(11) 0.93318(19) 0.0319(4) Uani 1 1 d .
C2 C 0.65971(7) 0.61071(12) 0.1329(2) 0.0350(5) Uani 1 1 d .
C9 C 0.50656(7) 0.38868(11) 0.60094(19) 0.0339(4) Uani 1 1 d .
C15 C 0.67112(7) 0.31941(11) 0.9941(2) 0.0356(5) Uani 1 1 d .
H18A H 0.6790 0.3193 1.0878 0.043 Uiso 1 1 calc R
H18B H 0.6366 0.3185 0.9863 0.043 Uiso 1 1 calc R
C21 C 0.72277(7) 0.43377(12) 1.0005(2) 0.0364(5) Uani 1 1 d .
H24 H 0.7354 0.4165 1.0803 0.044 Uiso 1 1 calc R
C10 C 0.54375(8) 0.42551(13) 0.5368(2) 0.0428(5) Uani 1 1 d .
H13 H 0.5546 0.4078 0.4555 0.051 Uiso 1 1 calc R
C3 C 0.62804(7) 0.57730(13) 0.0447(2) 0.0403(5) Uani 1 1 d .
H3 H 0.6218 0.6000 -0.0366 0.048 Uiso 1 1 calc R
C8 C 0.48412(7) 0.32022(11) 0.5415(2) 0.0361(5) Uani 1 1 d .
H11A H 0.4497 0.3227 0.5529 0.043 Uiso 1 1 calc R
H11B H 0.4908 0.3189 0.4471 0.043 Uiso 1 1 calc R
C14 C 0.49106(8) 0.41618(12) 0.7217(2) 0.0393(5) Uani 1 1 d .
H17 H 0.4659 0.3927 0.7656 0.047 Uiso 1 1 calc R
C20 C 0.73746(8) 0.50208(13) 0.9510(2) 0.0434(5) Uani 1 1 d .
H23 H 0.7594 0.5309 0.9981 0.052 Uiso 1 1 calc R
C1 C 0.68639(7) 0.68063(12) 0.0967(2) 0.0396(5) Uani 1 1 d .
H1C H 0.7163 0.6819 0.1451 0.048 Uiso 1 1 calc R
H1D H 0.6938 0.6795 0.0026 0.048 Uiso 1 1 calc R
C5 C 0.61428(8) 0.47684(13) 0.1967(2) 0.0481(6) Uani 1 1 d .
H5 H 0.5994 0.4317 0.2178 0.058 Uiso 1 1 calc R
C19 C 0.71987(8) 0.52749(13) 0.8326(2) 0.0465(6) Uani 1 1 d .
H22 H 0.7298 0.5735 0.7990 0.056 Uiso 1 1 calc R
C7 C 0.66775(8) 0.57655(12) 0.2541(2) 0.0421(5) Uani 1 1 d .
H7 H 0.6886 0.5985 0.3148 0.050 Uiso 1 1 calc R
C17 C 0.67188(8) 0.41665(13) 0.8133(2) 0.0423(5) Uani 1 1 d .
H20 H 0.6496 0.3884 0.7664 0.051 Uiso 1 1 calc R
C12 C 0.54966(8) 0.51425(13) 0.7136(2) 0.0475(6) Uani 1 1 d .
H15 H 0.5643 0.5558 0.7519 0.057 Uiso 1 1 calc R
C4 C 0.60569(8) 0.51072(13) 0.0767(2) 0.0456(5) Uani 1 1 d .
H4 H 0.5847 0.4887 0.0167 0.055 Uiso 1 1 calc R
C11 C 0.56467(8) 0.48800(14) 0.5923(2) 0.0494(6) Uani 1 1 d .
H14 H 0.5891 0.5126 0.5474 0.059 Uiso 1 1 calc R
C13 C 0.51265(8) 0.47843(12) 0.7778(2) 0.0452(5) Uani 1 1 d .
H16 H 0.5021 0.4962 0.8595 0.054 Uiso 1 1 calc R
C6 C 0.64503(9) 0.51006(13) 0.2857(2) 0.0478(6) Uani 1 1 d .
H6 H 0.6506 0.4876 0.3676 0.057 Uiso 1 1 calc R
C18 C 0.68724(9) 0.48461(13) 0.7632(2) 0.0491(6) Uani 1 1 d .
H21 H 0.6755 0.5016 0.6822 0.059 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
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
C15 N3 C15 111.7(2) . 8_565
C1 N1 C1 112.0(2) . 8_575
C8 N2 C8 113.5(2) 8_565 .
C26 C27 Cl5 113.98(18) . .
C26 C27 Cl6 109.14(11) . .
Cl5 C27 Cl6 108.10(10) . .
C26 C27 Cl6 109.14(11) . 8_565
Cl5 C27 Cl6 108.10(10) . 8_565
Cl6 C27 Cl6 108.23(14) . 8_565
C22 C23 Cl2 109.02(11) . .
C22 C23 Cl2 109.02(11) . 8_565
Cl2 C23 Cl2 108.98(15) . 8_565
C22 C23 Cl1 113.59(18) . .
Cl2 C23 Cl1 108.08(10) . .
Cl2 C23 Cl1 108.08(10) 8_565 .
O5 C26 O6 129.6(2) . .
O5 C26 C27 117.8(2) . .
O6 C26 C27 112.6(2) . .
O4 C24 O3 128.9(2) . .
O4 C24 C25 116.8(2) . .
O3 C24 C25 114.3(2) . .
O2 C22 O1 128.9(3) . .
O2 C22 C23 113.9(2) . .
O1 C22 C23 117.2(2) . .
C24 C25 Cl4 111.55(18) . .
C24 C25 Cl3 109.23(12) . .
Cl4 C25 Cl3 108.92(11) . .
C24 C25 Cl3 109.23(12) . 8_565
Cl4 C25 Cl3 108.92(11) . 8_565
Cl3 C25 Cl3 108.95(15) . 8_565
C21 C16 C17 118.54(19) . .
C21 C16 C15 120.07(18) . .
C17 C16 C15 121.27(19) . .
C7 C2 C3 118.7(2) . .
C7 C2 C1 120.02(19) . .
C3 C2 C1 121.28(19) . .
C14 C9 C10 118.5(2) . .
C14 C9 C8 120.64(18) . .
C10 C9 C8 120.87(18) . .
N3 C15 C16 113.53(16) . .
C20 C21 C16 121.0(2) . .
C11 C10 C9 120.8(2) . .
C4 C3 C2 120.6(2) . .
N2 C8 C9 111.49(15) . .
C9 C14 C13 120.5(2) . .
C19 C20 C21 120.1(2) . .
N1 C1 C2 112.38(16) . .
C4 C5 C6 119.6(2) . .
C20 C19 C18 119.8(2) . .
C6 C7 C2 120.4(2) . .
C18 C17 C16 120.2(2) . .
C11 C12 C13 119.3(2) . .
C5 C4 C3 120.3(2) . .
C12 C11 C10 120.4(2) . .
C12 C13 C14 120.5(2) . .
C5 C6 C7 120.5(2) . .
C19 C18 C17 120.4(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C23 1.768(3) .
Cl5 C27 1.764(3) .
Cl6 C27 1.7692(16) .
Cl4 C25 1.753(3) .
Cl2 C23 1.7589(16) .
Cl3 C25 1.7620(17) .
O4 C24 1.226(3) .
O1 C22 1.232(3) .
O2 C22 1.227(3) .
O3 C24 1.229(3) .
O6 C26 1.231(3) .
O5 C26 1.223(3) .
N3 C15 1.495(2) .
N3 C15 1.495(2) 8_565
N1 C1 1.492(2) .
N1 C1 1.492(2) 8_575
N2 C8 1.497(2) 8_565
N2 C8 1.497(2) .
C27 C26 1.570(3) .
C27 Cl6 1.7692(16) 8_565
C23 C22 1.569(4) .
C23 Cl2 1.7589(16) 8_565
C24 C25 1.576(4) .
C25 Cl3 1.7620(17) 8_565
C16 C21 1.386(3) .
C16 C17 1.386(3) .
C16 C15 1.498(3) .
C2 C7 1.383(3) .
C2 C3 1.389(3) .
C2 C1 1.498(3) .
C9 C14 1.382(3) .
C9 C10 1.390(3) .
C9 C8 1.498(3) .
C21 C20 1.379(3) .
C10 C11 1.377(3) .
C3 C4 1.380(3) .
C14 C13 1.384(3) .
C20 C19 1.367(3) .
C5 C4 1.373(3) .
C5 C6 1.376(3) .
C19 C18 1.381(3) .
C7 C6 1.382(3) .
C17 C18 1.381(3) .
C12 C11 1.374(3) .
C12 C13 1.378(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O4 0.90 2.49 3.126(3) 127.9 5_666
