#------------------------------------------------------------------------------
#$Date: 2019-11-26 04:49:55 +0100 (mar 26 de nov de 2019) $
#$Revision: 242753 $
#$URL: svn://www.crystallography.net/cod/cif/4/13/28/4132875.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_4132875
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            'C56.32 H73.09 F3.55 N9 O11.86 S3'
_chemical_formula_weight         1229.67
_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                   24.002(5)
_cell_length_b                   24.002(5)
_cell_length_c                   7.3978(14)
_cell_measurement_reflns_used    5522
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.60
_cell_measurement_theta_min      2.59
_cell_volume                     3690.9(13)
_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  0.0865
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            38883
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.430
_diffrn_reflns_theta_max         24.430
_diffrn_reflns_theta_min         1.697
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_description       needle
_exptl_crystal_F_000             1298
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1219 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4075
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0617
_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)+(0.1069P)²+0.3892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.1678
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3253
_reflns_number_total             4075
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b07065_si_002.cif
_cod_data_source_block           1prime-10min
_cod_original_cell_volume        3690.7(16)
_cod_database_code               4132875
_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   0.916
_shelx_estimated_absorpt_t_max   0.988
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.87232(6) 0.68869(6) 0.5864(2) 0.0432(4) Uani 1 1 d . . . . .
O1 O 0.9116(2) 0.7069(2) 0.4250(5) 0.0443(11) Uani 1 1 d . . . . .
O2 O 0.82954(16) 0.71453(16) 0.5885(7) 0.0452(8) Uani 1 1 d . . . . .
O3 O 0.9109(2) 0.7030(2) 0.7509(5) 0.0470(12) Uani 1 1 d . . . . .
C1 C 0.7058(3) 0.4006(3) 0.5509(8) 0.0456(15) Uani 1 1 d . . . . .
C2 C 0.6386(3) 0.3721(3) 0.5500(8) 0.0470(15) Uani 1 1 d . . . . .
H2 H 0.619582 0.398501 0.548714 0.056 Uiso 1 1 calc R U . . .
C3 C 0.7466(3) 0.4713(3) 0.5578(9) 0.0461(15) Uani 1 1 d . . . . .
C4 C 0.8053(3) 0.5005(3) 0.6512(9) 0.0509(16) Uani 1 1 d . . . . .
H4 H 0.819407 0.474165 0.707664 0.061 Uiso 1 1 calc R U . . .
C5 C 0.8427(3) 0.5655(3) 0.6632(9) 0.0486(15) Uani 1 1 d . . . . .
H5 H 0.882158 0.584299 0.727826 0.058 Uiso 1 1 calc R U . . .
C6 C 0.8225(2) 0.6039(3) 0.5805(10) 0.0447(12) Uani 1 1 d . . . . .
C7 C 0.7662(3) 0.5775(3) 0.4840(9) 0.0477(15) Uani 1 1 d . . . . .
H7 H 0.753490 0.604561 0.424854 0.057 Uiso 1 1 calc R U . . .
C8 C 0.7281(3) 0.5113(3) 0.4734(9) 0.0489(15) Uani 1 1 d . . . . .
H8 H 0.688775 0.492981 0.407825 0.059 Uiso 1 1 calc R U . . .
N1 N 0.8566(2) 0.7146(2) 0.0884(10) 0.0590(13) Uani 1 1 d . . . . .
H1A H 0.870047 0.707158 0.191405 0.071 Uiso 1 1 calc R U . . .
H1B H 0.870761 0.708038 -0.014613 0.071 Uiso 1 1 calc R U . . .
N2 N 0.7934(3) 0.7456(3) 0.2402(7) 0.0585(17) Uani 1 1 d . . . . .
H2A H 0.806476 0.738373 0.344280 0.070 Uiso 1 1 calc R U . . .
H2B H 0.765824 0.759563 0.238167 0.070 Uiso 1 1 calc R U . . .
N3 N 0.7935(3) 0.7448(3) -0.0676(7) 0.0551(16) Uani 1 1 d . . . . .
H3A H 0.764968 0.757622 -0.068132 0.066 Uiso 1 1 calc R U . . .
H3B H 0.807782 0.738234 -0.170410 0.066 Uiso 1 1 calc R U . . .
C9 C 0.8152(3) 0.7355(3) 0.0884(11) 0.0532(14) Uani 1 1 d . . . . .
O4 O 0.5692(2) 0.4747(2) 0.4997(8) 0.0655(15) Uani 0.954(7) 1 d . . P A 1
C10 C 0.5772(3) 0.5141(3) 0.6186(11) 0.0520(19) Uani 0.954(7) 1 d . . P A 1
C11 C 0.6133(3) 0.5211(3) 0.7879(11) 0.0566(17) Uani 0.954(7) 1 d . . P A 1
H11 H 0.629669 0.492802 0.808524 0.068 Uiso 0.954(7) 1 calc R U P A 1
C12 C 0.6235(3) 0.5646(3) 0.9096(10) 0.0537(17) Uani 0.954(7) 1 d . . P A 1
C13 C 0.6014(3) 0.6116(3) 0.8853(10) 0.0572(19) Uani 0.954(7) 1 d . . P A 1
H13A H 0.634919 0.653687 0.933233 0.069 Uiso 0.954(7) 1 calc R U P A 1
H13B H 0.562133 0.597549 0.958751 0.069 Uiso 0.954(7) 1 calc R U P A 1
C14 C 0.5867(3) 0.6211(3) 0.6913(10) 0.0498(16) Uani 0.954(7) 1 d . . P A 1
C15 C 0.5472(3) 0.5563(3) 0.6061(10) 0.0526(17) Uani 0.954(7) 1 d . . P A 1
H15A H 0.540446 0.562204 0.477074 0.063 Uiso 0.954(7) 1 calc R U P A 1
H15B H 0.504521 0.534035 0.665237 0.063 Uiso 0.954(7) 1 calc R U P A 1
C16 C 0.6583(4) 0.5694(4) 1.0791(15) 0.074(2) Uani 0.954(7) 1 d . . P A 1
H16A H 0.697518 0.611616 1.085401 0.111 Uiso 0.954(7) 1 calc R U P A 1
H16B H 0.669883 0.535578 1.081404 0.111 Uiso 0.954(7) 1 calc R U P A 1
H16C H 0.630717 0.564148 1.182791 0.111 Uiso 0.954(7) 1 calc R U P A 1
C17 C 0.6507(3) 0.6607(3) 0.5841(12) 0.0573(16) Uani 0.954(7) 1 d . . P A 1
H17A H 0.678657 0.642443 0.604652 0.086 Uiso 0.954(7) 1 calc R U P A 1
H17B H 0.672504 0.705516 0.625567 0.086 Uiso 0.954(7) 1 calc R U P A 1
H17C H 0.641183 0.659195 0.454811 0.086 Uiso 0.954(7) 1 calc R U P A 1
C18 C 0.5496(4) 0.6584(4) 0.6888(10) 0.0617(19) Uani 0.954(7) 1 d . . P A 1
H18A H 0.575173 0.699871 0.749646 0.093 Uiso 0.954(7) 1 calc R U P A 1
H18B H 0.508443 0.633255 0.751686 0.093 Uiso 0.954(7) 1 calc R U P A 1
H18C H 0.541667 0.665613 0.563344 0.093 Uiso 0.954(7) 1 calc R U P A 1
F1 F 0.3962(3) 0.5999(3) 0.5559(15) 0.092(3) Uani 0.592(9) 1 d . U P B 1
F2 F 0.2669(4) 0.5377(3) 0.5565(15) 0.095(3) Uani 0.592(9) 1 d . U P B 1
C1F C 0.3658(5) 0.6333(5) 0.5570(18) 0.060(3) Uani 0.592(9) 1 d D U P B 1
C2F C 0.2998(5) 0.6010(5) 0.5567(17) 0.059(3) Uani 0.592(9) 1 d D U P B 1
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 112.1(3) . .
O2 S1 O3 113.2(3) . .
O1 S1 O3 112.05(19) . .
O2 S1 C6 106.2(2) . .
O1 S1 C6 106.8(3) . .
O3 S1 C6 106.0(3) . .
C2 C1 C2 119.2(6) 3_665 .
C2 C1 C3 120.6(5) 3_665 .
C2 C1 C3 120.1(5) . .
C1 C2 C1 120.8(6) 2_655 .
C1 C2 H2 119.6 2_655 .
C1 C2 H2 119.6 . .
C8 C3 C4 117.7(5) . .
C8 C3 C1 121.3(5) . .
C4 C3 C1 121.0(5) . .
C5 C4 C3 121.8(6) . .
C5 C4 H4 119.1 . .
C3 C4 H4 119.1 . .
C4 C5 C6 119.2(5) . .
C4 C5 H5 120.4 . .
C6 C5 H5 120.4 . .
C7 C6 C5 121.2(5) . .
C7 C6 S1 119.0(5) . .
C5 C6 S1 119.7(4) . .
C6 C7 C8 119.5(6) . .
C6 C7 H7 120.3 . .
C8 C7 H7 120.3 . .
C7 C8 C3 120.7(6) . .
C7 C8 H8 119.7 . .
C3 C8 H8 119.7 . .
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 121.0(7) . .
N2 C9 N3 119.2(5) . .
N1 C9 N3 119.7(7) . .
O4 C10 C11 123.1(6) . .
O4 C10 C15 121.7(6) . .
C11 C10 C15 115.1(6) . .
C12 C11 C10 122.4(6) . .
C12 C11 H11 118.8 . .
C10 C11 H11 118.8 . .
C11 C12 C13 122.1(7) . .
C11 C12 C16 121.2(7) . .
C13 C12 C16 116.7(6) . .
C12 C13 C14 115.3(6) . .
C12 C13 H13A 108.5 . .
C14 C13 H13A 108.5 . .
C12 C13 H13B 108.5 . .
C14 C13 H13B 108.5 . .
H13A C13 H13B 107.5 . .
C15 C14 C13 108.4(6) . .
C15 C14 C18 110.3(6) . .
C13 C14 C18 109.9(6) . .
C15 C14 C17 109.8(6) . .
C13 C14 C17 109.9(6) . .
C18 C14 C17 108.5(5) . .
C14 C15 C10 113.8(5) . .
C14 C15 H15A 108.8 . .
C10 C15 H15A 108.8 . .
C14 C15 H15B 108.8 . .
C10 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 121.2(10) . 2_665
F1 C1F C2F 119.2(10) . .
C2F C1F C2F 119.6(11) 2_665 .
F2 C2F C1F 119.1(10) . 3_565
F2 C2F C1F 120.5(10) . .
C1F C2F C1F 120.4(11) 3_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.441(4) .
S1 O1 1.447(4) .
S1 O3 1.462(5) .
S1 C6 1.773(5) .
C1 C2 1.396(8) 3_665
C1 C2 1.401(8) .
C1 C3 1.477(8) .
C2 H2 0.9500 .
C3 C8 1.393(8) .
C3 C4 1.402(8) .
C4 C5 1.359(9) .
C4 H4 0.9500 .
C5 C6 1.378(8) .
C5 H5 0.9500 .
C6 C7 1.372(8) .
C7 C8 1.384(9) .
C7 H7 0.9500 .
C8 H8 0.9500 .
N1 C9 1.320(7) .
N1 H1A 0.8800 .
N1 H1B 0.8800 .
N2 C9 1.311(9) .
N2 H2A 0.8800 .
N2 H2B 0.8800 .
N3 C9 1.330(9) .
N3 H3A 0.8800 .
N3 H3B 0.8800 .
O4 C10 1.234(8) .
C10 C11 1.484(11) .
C10 C15 1.511(9) .
C11 C12 1.307(11) .
C11 H11 0.9500 .
C12 C13 1.478(10) .
C12 C16 1.480(12) .
C13 C14 1.521(10) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.496(9) .
C14 C18 1.547(9) .
C14 C17 1.559(9) .
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 1.324(12) .
F2 C2F 1.317(12) .
C1F C2F 1.362(14) 2_665
C1F C2F 1.373(11) .
