#------------------------------------------------------------------------------
#$Date: 2024-10-06 08:17:52 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295108 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/36/7133620.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_7133620
loop_
_publ_author_name
'Alimi, Lukman O.'
'Liu, Xin'
'Zhang, Gengwu'
'Moosa, Basem'
'Khashab, Niveen M.'
_publ_section_title
;
 Polar organic cages for efficiently separating azeotropic mixtures.
;
_journal_issue                   77
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10768
_journal_page_last               10771
_journal_paper_doi               10.1039/d4cc03520h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         '2(C H Cl3), C36 H42 N8 O6'
_chemical_formula_sum            'C38 H44 Cl6 N8 O6'
_chemical_formula_weight         921.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-12-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-06-09 deposited with the CCDC.	2024-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.7580(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.3748(3)
_cell_length_b                   14.5735(2)
_cell_length_c                   16.4860(2)
_cell_measurement_reflns_used    8823
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.144
_cell_measurement_theta_min      3.952
_cell_volume                     4192.44(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      120.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29392
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.581
_diffrn_reflns_theta_min         3.952
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    4.207
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0855 before and 0.0718 after correction.
The Ratio of minimum to maximum transmission is 0.8957.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       block
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   0.985
_exptl_transmission_factor_min   0.976
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.062
_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     274
_refine_ls_number_reflns         3687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0539P)²+8.4894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2965
_reflns_number_total             3687
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03520h2.cif
_cod_data_source_block           DIHO-cage@CHCl3
_cod_depositor_comments
'Adding full bibliography for 7133620--7133624.cif.'
_cod_original_cell_volume        4192.43(11)
_cod_database_code               7133620
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C2(H2A,H2B), C13(H13A,H13B), C14(H14A,H14B), C11(H11A,H11B),
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C10(H10), C15(H15), C18(H18), C3(H3A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
Cl1 Cl 0.33218(4) 0.83075(5) 0.51233(5) 0.0365(2) Uani 1 1 d . . . . .
Cl2 Cl 0.45568(4) 0.94975(5) 0.62878(5) 0.0371(2) Uani 1 1 d . . . . .
Cl3 Cl 0.48079(4) 0.75389(5) 0.62487(5) 0.0408(2) Uani 1 1 d . . . . .
O2 O 0.32699(11) 0.32079(13) 0.51571(13) 0.0254(4) Uani 1 1 d . . . . .
O1 O 0.56534(11) 0.56876(13) 0.67082(13) 0.0252(4) Uani 1 1 d . . . . .
O3 O 0.44986(12) 0.17239(14) 0.88376(12) 0.0269(4) Uani 1 1 d . . . . .
N1 N 0.22003(11) 0.35448(14) 0.73533(14) 0.0198(5) Uani 1 1 d . . . . .
N4 N 0.31221(12) 0.17961(14) 0.75753(14) 0.0210(5) Uani 1 1 d . . . . .
N2 N 0.25091(12) 0.42312(15) 0.57974(14) 0.0218(5) Uani 1 1 d . . . . .
N3 N 0.64670(12) 0.45964(15) 0.62174(14) 0.0219(5) Uani 1 1 d . . . . .
C16 C 0.42124(14) 0.17526(17) 0.72561(17) 0.0198(5) Uani 1 1 d . . . . .
C7 C 0.51559(14) 0.42791(17) 0.58823(17) 0.0206(5) Uani 1 1 d . . . . .
C4 C 0.37843(14) 0.45926(18) 0.60166(16) 0.0210(5) Uani 1 1 d . . . . .
C8 C 0.45394(14) 0.36721(18) 0.54856(17) 0.0217(5) Uani 1 1 d . . . . .
H8 H 0.458925 0.315029 0.516976 0.026 Uiso 1 1 calc R U . . .
C5 C 0.43935(14) 0.52126(18) 0.63907(17) 0.0217(5) Uani 1 1 d . . . . .
H5 H 0.434004 0.574173 0.669520 0.026 Uiso 1 1 calc R U . . .
C10 C 0.58794(14) 0.40778(18) 0.58440(16) 0.0212(5) Uani 1 1 d . . . . .
H10 H 0.591492 0.354511 0.553218 0.025 Uiso 1 1 calc R U . . .
C17 C 0.47433(15) 0.17351(17) 0.81733(17) 0.0207(5) Uani 1 1 d . . . . .
C12 C 0.21489(14) 0.42833(18) 0.79303(17) 0.0219(6) Uani 1 1 d . . . . .
H12A H 0.167918 0.419057 0.801703 0.026 Uiso 1 1 calc R U . . .
H12B H 0.209503 0.487537 0.761401 0.026 Uiso 1 1 calc R U . . .
C15 C 0.33899(14) 0.17913(17) 0.69918(17) 0.0221(6) Uani 1 1 d . . . . .
H15 H 0.304538 0.181348 0.637005 0.027 Uiso 1 1 calc R U . . .
C18 C 0.55182(14) 0.17429(17) 0.84059(17) 0.0217(5) Uani 1 1 d . . . . .
H18 H 0.587404 0.174164 0.902372 0.026 Uiso 1 1 calc R U . . .
C9 C 0.38580(14) 0.38212(17) 0.55467(16) 0.0204(5) Uani 1 1 d . . . . .
C3 C 0.30886(14) 0.47593(18) 0.61265(16) 0.0212(5) Uani 1 1 d . . . . .
H3A H 0.306676 0.528344 0.645724 0.025 Uiso 1 1 calc R U . . .
C2 C 0.18361(14) 0.44615(18) 0.59386(17) 0.0238(6) Uani 1 1 d . . . . .
H2A H 0.139660 0.457952 0.534898 0.029 Uiso 1 1 calc R U . . .
H2B H 0.193841 0.503038 0.630072 0.029 Uiso 1 1 calc R U . . .
C13 C 0.20655(14) 0.26534(17) 0.76741(17) 0.0220(5) Uani 1 1 d . . . . .
H13A H 0.151459 0.260129 0.752844 0.026 Uiso 1 1 calc R U . . .
H13B H 0.235760 0.263030 0.833765 0.026 Uiso 1 1 calc R U . . .
C6 C 0.50717(14) 0.50671(17) 0.63240(17) 0.0208(5) Uani 1 1 d . . . . .
C14 C 0.22946(14) 0.18348(17) 0.72687(18) 0.0229(6) Uani 1 1 d . . . . .
H14A H 0.211902 0.126160 0.744219 0.027 Uiso 1 1 calc R U . . .
H14B H 0.203941 0.188134 0.660358 0.027 Uiso 1 1 calc R U . . .
C11 C 0.71671(14) 0.43472(19) 0.61469(17) 0.0235(6) Uani 1 1 d . . . . .
H11A H 0.727479 0.481185 0.577893 0.028 Uiso 1 1 calc R U . . .
H11B H 0.709285 0.374850 0.583642 0.028 Uiso 1 1 calc R U . . .
C1 C 0.16298(14) 0.36976(18) 0.64175(17) 0.0221(5) Uani 1 1 d . . . . .
H1A H 0.113071 0.384348 0.641738 0.027 Uiso 1 1 calc R U . . .
H1B H 0.156606 0.312140 0.607413 0.027 Uiso 1 1 calc R U . . .
C19 C 0.43270(15) 0.84971(19) 0.56246(19) 0.0271(6) Uani 1 1 d . . . . .
H19 H 0.448903 0.858874 0.513115 0.033 Uiso 1 1 calc R U . . .
H1 H 0.5993(19) 0.553(2) 0.665(2) 0.030(10) Uiso 1 1 d . . . . .
H2 H 0.297(2) 0.337(3) 0.525(3) 0.046(13) Uiso 1 1 d . . . . .
H3 H 0.407(2) 0.175(2) 0.860(2) 0.034(10) Uiso 1 1 d . . . . .
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
_geom_angle_publ_flag
C9 O2 H2 106(3) . . ?
C6 O1 H1 109(3) . . ?
C17 O3 H3 106(3) . . ?
C12 N1 C13 110.03(19) . . ?
C12 N1 C1 109.66(19) . . ?
C13 N1 C1 109.94(19) . . ?
C15 N4 C14 119.0(2) . . ?
C3 N2 C2 118.5(2) . . ?
C10 N3 C11 118.6(2) . . ?
C17 C16 C15 120.9(2) . . ?
C18 C16 C17 119.3(2) 2_656 . ?
C18 C16 C15 119.8(2) 2_656 . ?
C8 C7 C10 119.6(2) . . ?
C8 C7 C6 119.4(2) . . ?
C6 C7 C10 121.1(2) . . ?
C5 C4 C9 119.4(2) . . ?
C5 C4 C3 119.1(2) . . ?
C9 C4 C3 121.5(2) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H8 119.5 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
N3 C10 C7 122.1(2) . . ?
N3 C10 H10 119.0 . . ?
C7 C10 H10 119.0 . . ?
O3 C17 C16 120.8(2) . . ?
O3 C17 C18 119.4(2) . . ?
C18 C17 C16 119.8(2) . . ?
N1 C12 H12A 108.6 . . ?
N1 C12 H12B 108.6 . . ?
N1 C12 C11 114.6(2) . 2_656 ?
H12A C12 H12B 107.6 . . ?
C11 C12 H12A 108.6 2_656 . ?
C11 C12 H12B 108.6 2_656 . ?
N4 C15 C16 121.6(2) . . ?
N4 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C16 C18 H18 119.6 2_656 . ?
C17 C18 C16 120.9(2) . 2_656 ?
C17 C18 H18 119.6 . . ?
O2 C9 C4 121.1(2) . . ?
O2 C9 C8 119.3(2) . . ?
C8 C9 C4 119.6(2) . . ?
N2 C3 C4 122.6(2) . . ?
N2 C3 H3A 118.7 . . ?
C4 C3 H3A 118.7 . . ?
N2 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
N2 C2 C1 111.7(2) . . ?
H2A C2 H2B 107.9 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
N1 C13 H13A 108.8 . . ?
N1 C13 H13B 108.8 . . ?
N1 C13 C14 113.8(2) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
O1 C6 C7 121.5(2) . . ?
O1 C6 C5 118.9(2) . . ?
C5 C6 C7 119.6(2) . . ?
N4 C14 C13 111.4(2) . . ?
N4 C14 H14A 109.4 . . ?
N4 C14 H14B 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N3 C11 C12 111.8(2) . 2_656 ?
N3 C11 H11A 109.3 . . ?
N3 C11 H11B 109.3 . . ?
C12 C11 H11A 109.3 2_656 . ?
C12 C11 H11B 109.3 2_656 . ?
H11A C11 H11B 107.9 . . ?
N1 C1 C2 114.1(2) . . ?
N1 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
C2 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
Cl1 C19 H19 108.1 . . ?
Cl2 C19 Cl1 110.38(15) . . ?
Cl2 C19 H19 108.1 . . ?
Cl3 C19 Cl1 110.28(15) . . ?
Cl3 C19 Cl2 111.76(15) . . ?
Cl3 C19 H19 108.1 . . ?
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
Cl1 C19 1.776(3) . ?
Cl2 C19 1.760(3) . ?
Cl3 C19 1.745(3) . ?
O2 C9 1.369(3) . ?
O2 H2 0.70(4) . ?
O1 C6 1.367(3) . ?
O1 H1 0.75(3) . ?
O3 C17 1.370(3) . ?
O3 H3 0.75(3) . ?
N1 C12 1.468(3) . ?
N1 C13 1.468(3) . ?
N1 C1 1.473(3) . ?
N4 C15 1.276(3) . ?
N4 C14 1.458(3) . ?
N2 C3 1.272(3) . ?
N2 C2 1.460(3) . ?
N3 C10 1.280(3) . ?
N3 C11 1.457(3) . ?
C16 C17 1.412(3) . ?
C16 C15 1.459(4) . ?
C16 C18 1.400(4) 2_656 ?
C7 C8 1.399(4) . ?
C7 C10 1.460(4) . ?
C7 C6 1.407(4) . ?
C4 C5 1.399(4) . ?
C4 C9 1.407(4) . ?
C4 C3 1.456(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(4) . ?
C10 H10 0.9500 . ?
C17 C18 1.379(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.525(3) 2_656 ?
C15 H15 0.9500 . ?
C18 H18 0.9500 . ?
C3 H3A 0.9500 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.515(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.525(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C19 H19 1.0000 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C17 C18 C16 179.9(2) . . . 2_656 ?
N1 C13 C14 N4 67.3(3) . . . . ?
N2 C2 C1 N1 66.7(3) . . . . ?
C16 C17 C18 C16 -1.1(3) . . . 2_656 ?
C7 C8 C9 O2 -179.4(2) . . . . ?
C7 C8 C9 C4 -0.2(4) . . . . ?
C4 C5 C6 O1 -179.3(2) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C8 C7 C10 N3 -178.0(2) . . . . ?
C8 C7 C6 O1 -178.9(2) . . . . ?
C8 C7 C6 C5 2.5(4) . . . . ?
C5 C4 C9 O2 -178.8(2) . . . . ?
C5 C4 C9 C8 2.0(4) . . . . ?
C5 C4 C3 N2 179.3(2) . . . . ?
C10 N3 C11 C12 -125.4(2) . . . 2_656 ?
C10 C7 C8 C9 177.0(2) . . . . ?
C10 C7 C6 O1 2.1(4) . . . . ?
C10 C7 C6 C5 -176.5(2) . . . . ?
C17 C16 C15 N4 -1.1(4) . . . . ?
C12 N1 C13 C14 -166.0(2) . . . . ?
C12 N1 C1 C2 74.4(3) . . . . ?
C15 N4 C14 C13 -123.5(2) . . . . ?
C15 C16 C17 O3 2.1(4) . . . . ?
C15 C16 C17 C18 -176.9(2) . . . . ?
C18 C16 C17 O3 -178.6(2) 2_656 . . . ?
C18 C16 C17 C18 2.4(3) 2_656 . . . ?
C18 C16 C15 N4 179.6(2) 2_656 . . . ?
C9 C4 C5 C6 -1.6(4) . . . . ?
C9 C4 C3 N2 -1.0(4) . . . . ?
C3 N2 C2 C1 -121.7(2) . . . . ?
C3 C4 C5 C6 178.2(2) . . . . ?
C3 C4 C9 O2 1.5(4) . . . . ?
C3 C4 C9 C8 -177.7(2) . . . . ?
C2 N2 C3 C4 -179.5(2) . . . . ?
C13 N1 C12 C11 74.1(3) . . . 2_656 ?
C13 N1 C1 C2 -164.5(2) . . . . ?
C6 C7 C8 C9 -2.1(4) . . . . ?
C6 C7 C10 N3 1.0(4) . . . . ?
C14 N4 C15 C16 -180.0(2) . . . . ?
C11 N3 C10 C7 -179.9(2) . . . . ?
C1 N1 C12 C11 -164.9(2) . . . 2_656 ?
C1 N1 C13 C14 73.1(3) . . . . ?
