#------------------------------------------------------------------------------
#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/95/4129550.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_4129550
loop_
_publ_author_name
'Tang, Yun-Zhi'
'Yu, Yin-Mei'
'Xiong, Jian-Bo'
'Tan, Yu-Hui'
'Wen, He-Rui'
_publ_section_title
;
 Unusual High-Temperature Reversible Phase-Transition Behavior,
 Structures, and Dielectric-Ferroelectric Properties of Two New Crown
 Ether Clathrates.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13345
_journal_page_last               13351
_journal_paper_doi               10.1021/jacs.5b08061
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C18 H38 B F4 N O6'
_chemical_formula_weight         451.30
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.381(3)
_cell_length_b                   12.051(2)
_cell_length_c                   14.234(3)
_cell_measurement_temperature    293(2)
_cell_volume                     2295.3(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0768
_diffrn_reflns_av_sigmaI/netI    0.0730
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20323
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_correction_T_min  0.9774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4502
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0706
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0810P)²+1.2185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1778
_refine_ls_wR_factor_ref         0.1923
_reflns_number_gt                3381
_reflns_number_total             4502
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b08061_si_002.cif
_cod_data_source_block           bf4
_cod_original_sg_symbol_H-M      Pca2(1)
_cod_database_code               4129550
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
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
C1 C 0.3477(4) 0.2442(3) 0.3063(3) 0.0521(10) Uani 1 1 d .
H1 H 0.4151 0.2309 0.2817 0.062 Uiso 1 1 calc R
C2 C 0.3477(4) 0.3550(4) 0.3504(3) 0.0681(13) Uani 1 1 d .
H2A H 0.2812 0.3724 0.3732 0.082 Uiso 1 1 calc R
H2B H 0.3664 0.4106 0.3044 0.082 Uiso 1 1 calc R
C6 C 0.3250(4) 0.1534(4) 0.3747(4) 0.0645(13) Uani 1 1 d .
H6A H 0.3288 0.0823 0.3431 0.077 Uiso 1 1 calc R
H6B H 0.2575 0.1625 0.3984 0.077 Uiso 1 1 calc R
C4 C 0.4000(6) 0.2661(5) 0.5004(4) 0.098(2) Uani 1 1 d .
H4A H 0.4500 0.2666 0.5497 0.118 Uiso 1 1 calc R
H4B H 0.3356 0.2802 0.5293 0.118 Uiso 1 1 calc R
C3 C 0.4223(6) 0.3564(5) 0.4328(4) 0.095(2) Uani 1 1 d .
H3A H 0.4897 0.3475 0.4088 0.114 Uiso 1 1 calc R
H3B H 0.4186 0.4275 0.4647 0.114 Uiso 1 1 calc R
C5 C 0.3983(5) 0.1554(5) 0.4563(4) 0.0823(17) Uani 1 1 d .
H5A H 0.3789 0.1003 0.5025 0.099 Uiso 1 1 calc R
H5B H 0.4646 0.1369 0.4337 0.099 Uiso 1 1 calc R
N1 N 0.2769(2) 0.2413(2) 0.2248(2) 0.0352(6) Uani 1 1 d .
H1A H 0.2150 0.2542 0.2450 0.053 Uiso 1 1 calc R
H1B H 0.2794 0.1748 0.1976 0.053 Uiso 1 1 calc R
H1C H 0.2941 0.2931 0.1833 0.053 Uiso 1 1 calc R
O2 O 0.1067(2) 0.0741(2) 0.2268(2) 0.0502(7) Uani 1 1 d .
O3 O 0.2955(2) 0.0131(2) 0.15790(19) 0.0496(7) Uani 1 1 d .
O4 O 0.4040(2) 0.1800(2) 0.0609(2) 0.0497(7) Uani 1 1 d .
O5 O 0.3724(2) 0.4073(2) 0.10380(19) 0.0514(7) Uani 1 1 d .
O1 O 0.07276(18) 0.3015(2) 0.27492(19) 0.0472(7) Uani 1 1 d .
O6 O 0.1820(2) 0.4616(2) 0.1724(2) 0.0534(7) Uani 1 1 d .
C17 C 0.1173(3) 0.4916(3) 0.2457(3) 0.0586(11) Uani 1 1 d .
H17A H 0.0903 0.5651 0.2344 0.070 Uiso 1 1 calc R
H17B H 0.1533 0.4929 0.3048 0.070 Uiso 1 1 calc R
C11 C 0.3552(4) -0.0081(4) 0.0768(3) 0.0582(11) Uani 1 1 d .
H11A H 0.3151 0.0003 0.0205 0.070 Uiso 1 1 calc R
H11B H 0.3805 -0.0835 0.0787 0.070 Uiso 1 1 calc R
C7 C -0.0031(3) 0.2204(4) 0.2710(4) 0.0599(11) Uani 1 1 d .
H7A H -0.0307 0.2175 0.2080 0.072 Uiso 1 1 calc R
H7B H -0.0564 0.2398 0.3141 0.072 Uiso 1 1 calc R
C12 C 0.4395(3) 0.0715(3) 0.0752(3) 0.0535(10) Uani 1 1 d .
H12A H 0.4755 0.0678 0.1343 0.064 Uiso 1 1 calc R
H12B H 0.4855 0.0518 0.0252 0.064 Uiso 1 1 calc R
C15 C 0.3205(3) 0.5049(4) 0.0755(3) 0.0581(11) Uani 1 1 d .
H15A H 0.2796 0.4890 0.0209 0.070 Uiso 1 1 calc R
H15B H 0.3681 0.5623 0.0586 0.070 Uiso 1 1 calc R
C18 C 0.0343(3) 0.4085(4) 0.2503(4) 0.0606(12) Uani 1 1 d .
H18A H -0.0145 0.4317 0.2967 0.073 Uiso 1 1 calc R
H18B H 0.0011 0.4043 0.1898 0.073 Uiso 1 1 calc R
C9 C 0.1506(3) -0.0294(3) 0.2477(3) 0.0544(11) Uani 1 1 d .
H9A H 0.0990 -0.0846 0.2577 0.065 Uiso 1 1 calc R
H9B H 0.1901 -0.0237 0.3047 0.065 Uiso 1 1 calc R
C13 C 0.4816(3) 0.2598(4) 0.0595(4) 0.0615(12) Uani 1 1 d .
H13A H 0.5327 0.2377 0.0149 0.074 Uiso 1 1 calc R
H13B H 0.5120 0.2652 0.1212 0.074 Uiso 1 1 calc R
C16 C 0.2574(4) 0.5436(3) 0.1526(4) 0.0600(12) Uani 1 1 d .
H16A H 0.2979 0.5562 0.2081 0.072 Uiso 1 1 calc R
H16B H 0.2259 0.6132 0.1354 0.072 Uiso 1 1 calc R
C8 C 0.0386(3) 0.1094(4) 0.2967(3) 0.0608(12) Uani 1 1 d .
H8A H 0.0725 0.1142 0.3568 0.073 Uiso 1 1 calc R
H8B H -0.0152 0.0559 0.3024 0.073 Uiso 1 1 calc R
C14 C 0.4392(4) 0.3688(4) 0.0320(3) 0.0647(13) Uani 1 1 d .
H14A H 0.4927 0.4221 0.0233 0.078 Uiso 1 1 calc R
H14B H 0.4034 0.3616 -0.0269 0.078 Uiso 1 1 calc R
B1 B 0.2477(4) 0.7448(4) 0.9167(4) 0.0569(12) Uani 1 1 d .
F1 F 0.1868(3) 0.6538(3) 0.9214(3) 0.1129(14) Uani 1 1 d .
F4 F 0.1948(2) 0.8425(2) 0.9142(3) 0.0886(10) Uani 1 1 d .
F3 F 0.3117(4) 0.7444(3) 0.9892(4) 0.140(2) Uani 1 1 d .
F2 F 0.2999(6) 0.7369(3) 0.8352(4) 0.174(3) Uani 1 1 d .
C10 C 0.2159(3) -0.0633(3) 0.1673(3) 0.0562(11) Uani 1 1 d .
H10A H 0.2423 -0.1371 0.1784 0.067 Uiso 1 1 calc R
H10B H 0.1770 -0.0650 0.1098 0.067 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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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
C2 C1 C6 112.6(4)
C2 C1 N1 110.5(4)
C6 C1 N1 111.0(3)
C1 C2 C3 109.5(4)
C1 C6 C5 110.8(4)
C5 C4 C3 113.0(5)
C4 C3 C2 110.8(5)
C4 C5 C6 110.5(5)
C9 O2 C8 112.7(3)
C10 O3 C11 112.4(3)
C12 O4 C13 112.8(3)
C15 O5 C14 111.7(3)
C7 O1 C18 110.9(3)
C17 O6 C16 113.7(3)
O6 C17 C18 108.5(3)
O3 C11 C12 108.8(3)
O1 C7 C8 110.0(4)
O4 C12 C11 110.3(3)
O5 C15 C16 109.5(4)
O1 C18 C17 110.3(3)
O2 C9 C10 108.8(3)
O4 C13 C14 109.0(4)
O6 C16 C15 109.5(3)
O2 C8 C7 109.7(3)
O5 C14 C13 109.7(3)
F3 B1 F2 109.1(6)
F3 B1 F1 109.8(5)
F2 B1 F1 107.0(5)
F3 B1 F4 110.7(5)
F2 B1 F4 107.7(5)
F1 B1 F4 112.5(5)
O3 C10 C9 109.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.475(6)
C1 C6 1.496(6)
C1 N1 1.499(5)
C2 C3 1.540(7)
C6 C5 1.520(7)
C4 C5 1.475(8)
C4 C3 1.484(8)
O2 C9 1.411(5)
O2 C8 1.414(5)
O3 C10 1.415(5)
O3 C11 1.426(5)
O4 C12 1.406(5)
O4 C13 1.415(5)
O5 C15 1.424(5)
O5 C14 1.434(5)
O1 C7 1.411(5)
O1 C18 1.431(5)
O6 C17 1.403(5)
O6 C16 1.440(5)
C17 C18 1.497(6)
C11 C12 1.481(6)
C7 C8 1.494(6)
C15 C16 1.461(7)
C9 C10 1.496(6)
C13 C14 1.483(6)
B1 F3 1.341(7)
B1 F2 1.357(8)
B1 F1 1.368(6)
B1 F4 1.374(6)
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
N1 H1C O6 0.89 2.53 3.036(4) 116.8
N1 H1C O5 0.89 2.07 2.933(4) 164.1
N1 H1B O4 0.89 2.56 2.980(4) 109.4
N1 H1B O3 0.89 2.04 2.920(4) 169.7
N1 H1A O2 0.89 2.62 3.040(4) 109.7
N1 H1A O1 0.89 2.03 2.915(4) 171.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168334297
