#------------------------------------------------------------------------------
#$Date: 2022-09-19 01:59:28 +0300 (Mon, 19 Sep 2022) $
#$Revision: 277968 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/12/7711270.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_7711270
loop_
_publ_author_name
'Ye, Xing'
'He, Wenhui'
'Wei, Jing'
'Wei, Zhenhong'
'You, Xiuli'
'Cai, Hu'
_publ_section_title
;
 Two host--guest grown ether supramolecules show switchable phase
 transition, dielectric and second-harmonic generation effect
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT01826H
_journal_year                    2022
_chemical_formula_sum            'C17 H28 Cl F2 N O9'
_chemical_formula_weight         463.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-04-12 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.773(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.475(2)
_cell_length_b                   9.1044(12)
_cell_length_c                   15.932(2)
_cell_measurement_reflns_used    1865
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.0840
_cell_measurement_theta_min      2.8570
_cell_volume                     2197.4(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12928
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_min         1.344
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0732
_refine_ls_shift/su_max          0.051
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2488
_refine_ls_wR_factor_ref         0.3006
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2985
_reflns_number_total             4979
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt01826h2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               7711270
_shelx_shelxl_version_number     2014/7
_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, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O8 O 0.4554(6) 0.7293(10) 0.1895(4) 0.304(6) Uani 1 1 d . . . . .
O10 O 0.5451(8) 0.8852(11) 0.2090(6) 0.375(8) Uani 1 1 d . . . . .
Cl1 Cl 0.0000 0.86486(13) 0.2500 0.0605(4) Uani 1 2 d S T P . .
O7 O 0.0671(4) 0.7787(6) 0.2328(3) 0.173(2) Uani 1 1 d . . . . .
O6 O -0.0306(3) 0.9497(4) 0.1768(2) 0.1237(13) Uani 1 1 d . . . . .
Cl2 Cl 0.5000 0.80793(15) 0.2500 0.0724(4) Uani 1 2 d S T P . .
O2 O 0.78484(14) 0.6229(2) 0.02377(13) 0.0570(6) Uani 1 1 d . . . . .
O3 O 0.89391(16) 0.3729(3) 0.01488(16) 0.0670(7) Uani 1 1 d . . . . .
O5 O 0.66411(15) 0.2056(3) 0.04497(18) 0.0678(7) Uani 1 1 d . . . . .
O1 O 0.61414(15) 0.5054(3) 0.02737(15) 0.0641(7) Uani 1 1 d . . . . .
N1 N 0.71596(16) 0.3916(3) 0.90663(15) 0.0489(6) Uani 1 1 d . . . . .
H1A H 0.7454 0.4463 0.9494 0.073 Uiso 1 1 calc R U . . .
H1B H 0.7274 0.2971 0.9182 0.073 Uiso 1 1 calc R U . . .
H1C H 0.6583 0.4076 0.9008 0.073 Uiso 1 1 calc R U . . .
O4 O 0.79136(17) 0.1144(2) -0.04205(17) 0.0701(7) Uani 1 1 d . . . . .
C11 C 0.74400(19) 0.5942(3) 0.81175(17) 0.0485(7) Uani 1 1 d . . . . .
F2 F 0.59859(17) 0.6202(3) 0.82574(19) 0.1041(9) Uani 1 1 d . . . . .
C5 C 0.8788(2) 0.6264(4) 0.0427(3) 0.0703(10) Uani 1 1 d . . . . .
H5A H 0.8986 0.7035 0.0842 0.084 Uiso 1 1 calc R U . . .
H5B H 0.8996 0.6502 -0.0092 0.084 Uiso 1 1 calc R U . . .
C4 C 0.7448(3) 0.6394(4) 0.0961(2) 0.0634(9) Uani 1 1 d . . . . .
H4A H 0.7639 0.7302 0.1260 0.076 Uiso 1 1 calc R U . . .
H4B H 0.7608 0.5582 0.1356 0.076 Uiso 1 1 calc R U . . .
C12 C 0.6727(3) 0.6852(4) 0.8115(2) 0.0646(9) Uani 1 1 d . . . . .
C16 C 0.8181(2) 0.6668(5) 0.7963(2) 0.0661(9) Uani 1 1 d . . . . .
C3 C 0.6469(2) 0.6418(4) 0.0624(3) 0.0685(10) Uani 1 1 d . . . . .
H3A H 0.6175 0.6676 0.1086 0.082 Uiso 1 1 calc R U . . .
H3B H 0.6330 0.7170 0.0185 0.082 Uiso 1 1 calc R U . . .
C17 C 0.7438(3) 0.4310(4) 0.8265(2) 0.0636(9) Uani 1 1 d . . . . .
H17A H 0.7042 0.3848 0.7787 0.076 Uiso 1 1 calc R U . . .
H17B H 0.8026 0.3928 0.8283 0.076 Uiso 1 1 calc R U . . .
F1 F 0.88952(16) 0.5829(3) 0.79461(18) 0.1063(9) Uani 1 1 d . . . . .
C1 C 0.5804(2) 0.2559(5) 0.0536(3) 0.0753(11) Uani 1 1 d . . . . .
H1D H 0.5566 0.1924 0.0922 0.090 Uiso 1 1 calc R U . . .
H1E H 0.5401 0.2550 -0.0017 0.090 Uiso 1 1 calc R U . . .
C10 C 0.6624(3) 0.0618(4) 0.0124(3) 0.0834(12) Uani 1 1 d . . . . .
H10A H 0.6284 0.0584 -0.0459 0.100 Uiso 1 1 calc R U . . .
H10B H 0.6359 -0.0050 0.0473 0.100 Uiso 1 1 calc R U . . .
C8 C 0.8868(3) 0.1225(5) -0.0220(4) 0.0879(14) Uani 1 1 d . . . . .
H8A H 0.9077 0.1490 -0.0734 0.106 Uiso 1 1 calc R U . . .
H8B H 0.9105 0.0265 -0.0038 0.106 Uiso 1 1 calc R U . . .
C6 C 0.9189(2) 0.4832(5) 0.0776(2) 0.0763(11) Uani 1 1 d . . . . .
H6A H 0.9827 0.4917 0.0919 0.092 Uiso 1 1 calc R U . . .
H6B H 0.8983 0.4577 0.1293 0.092 Uiso 1 1 calc R U . . .
C2 C 0.5903(3) 0.4099(5) 0.0886(3) 0.0729(10) Uani 1 1 d . . . . .
H2A H 0.5351 0.4421 0.1024 0.087 Uiso 1 1 calc R U . . .
H2B H 0.6353 0.4120 0.1408 0.087 Uiso 1 1 calc R U . . .
C7 C 0.9200(2) 0.2307(5) 0.0460(3) 0.0771(11) Uani 1 1 d . . . . .
H7A H 0.8960 0.2097 0.0964 0.092 Uiso 1 1 calc R U . . .
H7B H 0.9838 0.2253 0.0620 0.092 Uiso 1 1 calc R U . . .
C9 C 0.7564(3) 0.0198(4) 0.0145(3) 0.0758(11) Uani 1 1 d . . . . .
H9A H 0.7908 0.0293 0.0724 0.091 Uiso 1 1 calc R U . . .
H9B H 0.7594 -0.0816 -0.0034 0.091 Uiso 1 1 calc R U . . .
C15 C 0.8197(4) 0.8150(6) 0.7813(3) 0.0998(17) Uani 1 1 d . . . . .
H15 H 0.8707 0.8601 0.7715 0.120 Uiso 1 1 calc R U . . .
C14 C 0.7450(6) 0.8951(6) 0.7809(3) 0.117(2) Uani 1 1 d . . . . .
H14 H 0.7448 0.9952 0.7693 0.140 Uiso 1 1 calc R U . . .
C13 C 0.6728(4) 0.8326(6) 0.7970(3) 0.1016(17) Uani 1 1 d . . . . .
H13 H 0.6229 0.8886 0.7984 0.122 Uiso 1 1 calc R U . . .
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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 Cl1 O7 110.3(6) . 2 ?
O7 Cl1 O6 110.0(3) . 2 ?
O7 Cl1 O6 106.8(3) 2 2 ?
O7 Cl1 O6 106.8(3) . . ?
O7 Cl1 O6 110.0(3) 2 . ?
O6 Cl1 O6 113.0(4) 2 . ?
O10 Cl2 O10 112.3(10) 2_655 . ?
O10 Cl2 O8 115.5(8) 2_655 . ?
O10 Cl2 O8 101.0(5) . . ?
O10 Cl2 O8 101.0(5) 2_655 2_655 ?
O10 Cl2 O8 115.5(8) . 2_655 ?
O8 Cl2 O8 112.2(8) . 2_655 ?
C5 O2 C4 114.9(3) . . ?
C6 O3 C7 112.6(3) . . ?
C1 O5 C10 113.0(3) . . ?
C2 O1 C3 113.1(3) . . ?
C9 O4 C8 113.1(3) . . ?
C12 C11 C16 113.7(3) . . ?
C12 C11 C17 124.5(3) . . ?
C16 C11 C17 121.8(3) . . ?
O2 C5 C6 112.7(3) . . ?
O2 C4 C3 106.7(3) . . ?
F2 C12 C11 116.3(3) . . ?
F2 C12 C13 119.4(4) . . ?
C11 C12 C13 124.3(4) . . ?
F1 C16 C15 120.7(4) . . ?
F1 C16 C11 116.3(4) . . ?
C15 C16 C11 123.0(4) . . ?
O1 C3 C4 112.5(3) . . ?
N1 C17 C11 112.7(3) . . ?
O5 C1 C2 108.2(3) . . ?
O5 C10 C9 106.5(3) . . ?
O4 C8 C7 112.4(3) . . ?
O3 C6 C5 108.8(3) . . ?
O1 C2 C1 109.8(3) . . ?
O3 C7 C8 108.7(3) . . ?
O4 C9 C10 108.8(3) . . ?
C14 C15 C16 118.7(5) . . ?
C13 C14 C15 121.1(5) . . ?
C14 C13 C12 119.1(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 Cl2 1.283(6) . ?
O10 Cl2 1.263(6) . ?
Cl1 O7 1.373(4) . ?
Cl1 O7 1.373(4) 2 ?
Cl1 O6 1.399(3) 2 ?
Cl1 O6 1.399(3) . ?
Cl2 O10 1.263(6) 2_655 ?
Cl2 O8 1.283(6) 2_655 ?
O2 C5 1.424(4) . ?
O2 C4 1.423(4) . ?
O3 C6 1.414(5) . ?
O3 C7 1.415(4) . ?
O5 C1 1.408(4) . ?
O5 C10 1.407(5) . ?
O1 C2 1.411(4) . ?
O1 C3 1.412(4) . ?
N1 C17 1.472(4) . ?
O4 C9 1.431(4) . ?
O4 C8 1.448(5) . ?
C11 C12 1.378(5) . ?
C11 C16 1.389(5) . ?
C11 C17 1.505(5) . ?
F2 C12 1.351(4) . ?
C5 C6 1.501(5) . ?
C4 C3 1.501(5) . ?
C12 C13 1.362(6) . ?
C16 F1 1.348(5) . ?
C16 C15 1.371(7) . ?
C1 C2 1.505(5) . ?
C10 C9 1.497(5) . ?
C8 C7 1.478(6) . ?
C15 C14 1.366(8) . ?
C14 C13 1.324(8) . ?
