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#$Date: 2019-11-26 05:49:55 +0200 (Tue, 26 Nov 2019) $
#$Revision: 242753 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/28/4132866.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_4132866
loop_
_publ_author_name
'Li, Yuantao'
'Handke, Marcel'
'Chen, Yu-Sheng'
'Shtukenberg, Alexander G.'
'Hu, Chunhua T.'
'Ward, Michael D.'
_publ_section_title
;
 Guest Exchange through Facilitated Transport in a Seemingly Impenetrable
 Hydrogen-Bonded Framework.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12915
_journal_page_last               12921
_journal_paper_doi               10.1021/jacs.8b07065
_journal_volume                  140
_journal_year                    2018
_chemical_formula_sum            'C58.71 H75 F4.71 N9 O12 S3'
_chemical_formula_weight         1284.39
_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_Hall           'P 6c'
_space_group_name_H-M_alt        'P 63'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   24.069(2)
_cell_length_b                   24.069(2)
_cell_length_c                   7.3724(7)
_cell_measurement_reflns_used    6486
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.96
_cell_measurement_theta_min      2.59
_cell_volume                     3698.8(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            43104
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.741
_diffrn_reflns_theta_max         24.741
_diffrn_reflns_theta_min         1.692
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_description       rod
_exptl_crystal_F_000             1353
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1467 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4221
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0693P)²+0.3988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3722
_reflns_number_total             4221
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b07065_si_002.cif
_cod_data_source_block           2
_cod_original_cell_volume        3698.7(8)
_cod_database_code               4132866
_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.
;
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, 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
S1 S 0.12741(5) 0.31189(5) 0.4112(2) 0.0384(3) Uani 1 1 d . . .
O1 O 0.08821(19) 0.29429(18) 0.5739(5) 0.0429(9) Uani 1 1 d . . .
O2 O 0.17014(14) 0.28580(13) 0.4082(6) 0.0416(7) Uani 1 1 d . . .
O3 O 0.08871(19) 0.29695(18) 0.2475(4) 0.0417(10) Uani 1 1 d . . .
C1 C 0.2943(2) 0.5997(2) 0.4468(7) 0.0424(12) Uani 1 1 d . . .
C2 C 0.3609(2) 0.6279(2) 0.4478(7) 0.0449(13) Uani 1 1 d . . .
H2 H 0.379817 0.601476 0.449166 0.054 Uiso 1 1 calc R U .
C3 C 0.2527(2) 0.5285(2) 0.4403(8) 0.0413(12) Uani 1 1 d . . .
C4 C 0.1948(3) 0.5003(3) 0.3455(8) 0.0479(14) Uani 1 1 d . . .
H4 H 0.181402 0.526832 0.287250 0.058 Uiso 1 1 calc R U .
C5 C 0.1568(2) 0.4348(2) 0.3350(7) 0.0421(12) Uani 1 1 d . . .
H5 H 0.116952 0.416175 0.272467 0.051 Uiso 1 1 calc R U .
C6 C 0.1769(2) 0.3961(2) 0.4162(9) 0.0421(10) Uani 1 1 d . . .
C7 C 0.2345(2) 0.4234(2) 0.5128(7) 0.0426(12) Uani 1 1 d . . .
H7 H 0.247818 0.396845 0.571323 0.051 Uiso 1 1 calc R U .
C8 C 0.2716(2) 0.4889(2) 0.5225(7) 0.0442(12) Uani 1 1 d . . .
H8 H 0.311113 0.507499 0.586872 0.053 Uiso 1 1 calc R U .
N1 N 0.14441(19) 0.2863(2) 0.9084(8) 0.0535(10) Uani 1 1 d . . .
H1A H 0.130328 0.292913 0.805122 0.064 Uiso 1 1 calc R U .
H1B H 0.130779 0.293352 1.011861 0.064 Uiso 1 1 calc R U .
N2 N 0.2068(3) 0.2549(3) 0.7552(6) 0.0555(15) Uani 1 1 d . . .
H2A H 0.193014 0.261408 0.651217 0.067 Uiso 1 1 calc R U .
H2B H 0.234526 0.241209 0.756526 0.067 Uiso 1 1 calc R U .
N3 N 0.2077(3) 0.2562(3) 1.0657(6) 0.0532(14) Uani 1 1 d . . .
H3A H 0.235716 0.242860 1.066182 0.064 Uiso 1 1 calc R U .
H3B H 0.193944 0.263365 1.168823 0.064 Uiso 1 1 calc R U .
C9 C 0.1861(2) 0.2657(2) 0.9081(9) 0.0492(11) Uani 1 1 d . . .
O4 O 0.43065(19) 0.52553(19) 0.4971(6) 0.0606(11) Uani 1 1 d . . .
C10 C 0.4230(2) 0.4863(2) 0.3789(8) 0.0476(15) Uani 1 1 d . . .
C11 C 0.3867(3) 0.4793(3) 0.2134(9) 0.0500(13) Uani 1 1 d . . .
H11 H 0.369820 0.507033 0.194558 0.060 Uiso 1 1 calc R U .
C12 C 0.3764(3) 0.4354(3) 0.0881(8) 0.0472(12) Uani 1 1 d . . .
C13 C 0.3991(3) 0.3884(3) 0.1104(7) 0.0478(13) Uani 1 1 d . . .
H13A H 0.438797 0.403332 0.038450 0.057 Uiso 1 1 calc R U .
H13B H 0.366250 0.346668 0.059538 0.057 Uiso 1 1 calc R U .
C14 C 0.4128(3) 0.3779(3) 0.3081(8) 0.0466(12) Uani 1 1 d . . .
C15 C 0.4531(2) 0.4447(2) 0.3939(8) 0.0482(12) Uani 1 1 d . . .
H15A H 0.459870 0.439370 0.523776 0.058 Uiso 1 1 calc R U .
H15B H 0.495657 0.466772 0.334537 0.058 Uiso 1 1 calc R U .
C16 C 0.3416(3) 0.4310(3) -0.0838(12) 0.0625(14) Uani 1 1 d . . .
H16A H 0.303512 0.388297 -0.093485 0.094 Uiso 1 1 calc R U .
H16B H 0.369956 0.438285 -0.187467 0.094 Uiso 1 1 calc R U .
H16C H 0.328563 0.463596 -0.083242 0.094 Uiso 1 1 calc R U .
C17 C 0.3496(2) 0.3396(2) 0.4118(9) 0.0496(11) Uani 1 1 d . . .
H17A H 0.325725 0.362674 0.408458 0.074 Uiso 1 1 calc R U .
H17B H 0.358764 0.334171 0.538035 0.074 Uiso 1 1 calc R U .
H17C H 0.323972 0.297356 0.355212 0.074 Uiso 1 1 calc R U .
C18 C 0.4497(3) 0.3425(3) 0.3122(8) 0.0557(14) Uani 1 1 d . . .
H18A H 0.423848 0.300047 0.257241 0.083 Uiso 1 1 calc R U .
H18B H 0.459622 0.337656 0.438193 0.083 Uiso 1 1 calc R U .
H18C H 0.489776 0.366841 0.243951 0.083 Uiso 1 1 calc R U .
F1 F 0.6037(2) 0.4000(2) 0.4417(10) 0.0854(18) Uani 0.785(6) 1 d . . P
F2 F 0.7329(2) 0.4629(2) 0.4424(9) 0.0853(18) Uani 0.785(6) 1 d . . P
C1F C 0.6348(4) 0.3672(4) 0.4426(10) 0.0553(19) Uani 0.785(6) 1 d . . P
C2F C 0.7004(4) 0.3991(3) 0.4429(10) 0.0546(19) Uani 0.785(6) 1 d . . P
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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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
O2 S1 O1 112.6(2) . .
O2 S1 O3 112.7(2) . .
O1 S1 O3 111.77(16) . .
O2 S1 C6 106.27(18) . .
O1 S1 C6 106.6(3) . .
O3 S1 C6 106.4(3) . .
C2 C1 C2 119.0(5) . 3_565
C2 C1 C3 120.6(4) . .
C2 C1 C3 120.4(4) 3_565 .
C1 C2 C1 121.0(5) . 2_665
C1 C2 H2 119.5 . .
C1 C2 H2 119.5 2_665 .
C8 C3 C4 118.5(5) . .
C8 C3 C1 120.8(4) . .
C4 C3 C1 120.6(5) . .
C5 C4 C3 121.1(5) . .
C5 C4 H4 119.4 . .
C3 C4 H4 119.4 . .
C4 C5 C6 119.5(5) . .
C4 C5 H5 120.3 . .
C6 C5 H5 120.3 . .
C5 C6 C7 120.3(4) . .
C5 C6 S1 120.1(4) . .
C7 C6 S1 119.5(4) . .
C8 C7 C6 119.4(5) . .
C8 C7 H7 120.3 . .
C6 C7 H7 120.3 . .
C7 C8 C3 121.2(5) . .
C7 C8 H8 119.4 . .
C3 C8 H8 119.4 . .
C9 N1 H1A 120.0 . .
C9 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
C9 N2 H2A 120.0 . .
C9 N2 H2B 120.0 . .
H2A N2 H2B 120.0 . .
C9 N3 H3A 120.0 . .
C9 N3 H3B 120.0 . .
H3A N3 H3B 120.0 . .
N2 C9 N1 120.7(6) . .
N2 C9 N3 119.6(4) . .
N1 C9 N3 119.7(6) . .
O4 C10 C11 122.2(5) . .
O4 C10 C15 121.5(5) . .
C11 C10 C15 116.3(5) . .
C12 C11 C10 122.4(5) . .
C12 C11 H11 118.8 . .
C10 C11 H11 118.8 . .
C11 C12 C13 122.2(5) . .
C11 C12 C16 121.3(5) . .
C13 C12 C16 116.5(5) . .
C12 C13 C14 114.7(5) . .
C12 C13 H13A 108.6 . .
C14 C13 H13A 108.6 . .
C12 C13 H13B 108.6 . .
C14 C13 H13B 108.6 . .
H13A C13 H13B 107.6 . .
C18 C14 C17 109.7(4) . .
C18 C14 C15 109.9(4) . .
C17 C14 C15 110.0(5) . .
C18 C14 C13 110.3(5) . .
C17 C14 C13 110.0(5) . .
C15 C14 C13 107.0(4) . .
C10 C15 C14 113.8(4) . .
C10 C15 H15A 108.8 . .
C14 C15 H15A 108.8 . .
C10 C15 H15B 108.8 . .
C14 C15 H15B 108.8 . .
H15A C15 H15B 107.7 . .
C12 C16 H16A 109.5 . .
C12 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C12 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C14 C17 H17A 109.5 . .
C14 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C14 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C14 C18 H18A 109.5 . .
C14 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C14 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
F1 C1F C2F 120.1(7) . .
F1 C1F C2F 119.9(7) . 2_655
C2F C1F C2F 120.1(7) . 2_655
F2 C2F C1F 119.8(7) . .
F2 C2F C1F 120.3(7) . 3_665
C1F C2F C1F 119.9(7) . 3_665
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.449(3) .
S1 O1 1.452(4) .
S1 O3 1.456(4) .
S1 C6 1.765(5) .
C1 C2 1.393(7) .
C1 C2 1.399(7) 3_565
C1 C3 1.491(7) .
C2 H2 0.9500 .
C3 C8 1.385(7) .
C3 C4 1.395(7) .
C4 C5 1.374(8) .
C4 H4 0.9500 .
C5 C6 1.382(7) .
C5 H5 0.9500 .
C6 C7 1.396(7) .
C7 C8 1.372(7) .
C7 H7 0.9500 .
C8 H8 0.9500 .
N1 C9 1.322(6) .
N1 H1A 0.8800 .
N1 H1B 0.8800 .
N2 C9 1.310(8) .
N2 H2A 0.8800 .
N2 H2B 0.8800 .
N3 C9 1.338(8) .
N3 H3A 0.8800 .
N3 H3B 0.8800 .
O4 C10 1.229(7) .
C10 C11 1.461(8) .
C10 C15 1.506(7) .
C11 C12 1.330(8) .
C11 H11 0.9500 .
C12 C13 1.489(8) .
C12 C16 1.494(9) .
C13 C14 1.543(8) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C18 1.509(8) .
C14 C17 1.531(8) .
C14 C15 1.538(7) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
F1 C1F 1.331(8) .
F2 C2F 1.329(8) .
C1F C2F 1.367(10) .
C1F C2F 1.375(10) 2_655
