#------------------------------------------------------------------------------
#$Date: 2019-11-26 05:49:55 +0200 (Tue, 26 Nov 2019) $
#$Revision: 242753 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/28/4132872.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_4132872
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            'C53.9 H69.35 F3.53 N9 O11.6 S3'
_chemical_formula_weight         1192.17
_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                   24.102(13)
_cell_length_b                   24.102(13)
_cell_length_c                   7.467(4)
_cell_measurement_reflns_used    3262
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.38
_cell_measurement_theta_min      2.58
_cell_volume                     3756(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1242
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_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            31659
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        23.856
_diffrn_reflns_theta_max         23.856
_diffrn_reflns_theta_min         1.690
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_correction_T_min  0.6033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.054
_exptl_crystal_description       needle
_exptl_crystal_F_000             1257
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.108
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details
;
 Flack x determined using 1070 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3884
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.1013
_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)+(0.1711P)²+3.7198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2538
_refine_ls_wR_factor_ref         0.2711
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3077
_reflns_number_total             3884
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b07065_si_002.cif
_cod_data_source_block           1-22min
_cod_original_formula_sum        'C53.90 H69.35 F3.53 N9 O11.60 S3'
_cod_database_code               4132872
_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   0.939
_shelx_estimated_absorpt_t_max   0.990
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 0.12774(11) 0.31113(11) 0.4143(4) 0.0459(7) Uani 1 1 d . . . . .
O1 O 0.0883(4) 0.2926(4) 0.5734(10) 0.047(2) Uani 1 1 d . . . . .
O2 O 0.1699(3) 0.2859(3) 0.4108(11) 0.0457(16) Uani 1 1 d . . . . .
O3 O 0.0898(4) 0.2974(4) 0.2490(10) 0.051(2) Uani 1 1 d . . . . .
C1 C 0.2946(5) 0.5993(5) 0.4506(11) 0.039(2) Uani 1 1 d . . . . .
C2 C 0.3624(5) 0.6277(5) 0.4509(12) 0.045(3) Uani 1 1 d . . . . .
H2 H 0.381742 0.601737 0.451303 0.054 Uiso 1 1 calc R U . . .
C3 C 0.2538(5) 0.5289(5) 0.4473(13) 0.040(2) Uani 1 1 d . . . . .
C4 C 0.1933(5) 0.4983(6) 0.3501(16) 0.053(3) Uani 1 1 d . . . . .
H4 H 0.179126 0.524207 0.292786 0.064 Uiso 1 1 calc R U . . .
C5 C 0.1579(5) 0.4354(6) 0.3404(15) 0.051(3) Uani 1 1 d . . . . .
H5 H 0.118285 0.416550 0.277738 0.062 Uiso 1 1 calc R U . . .
C6 C 0.1778(4) 0.3963(5) 0.4207(17) 0.047(2) Uani 1 1 d . . . . .
C7 C 0.2346(5) 0.4226(5) 0.5150(15) 0.048(3) Uani 1 1 d . . . . .
H7 H 0.247584 0.395867 0.573226 0.057 Uiso 1 1 calc R U . . .
C8 C 0.2732(5) 0.4902(5) 0.5231(17) 0.050(3) Uani 1 1 d . . . . .
H8 H 0.313335 0.508759 0.582775 0.060 Uiso 1 1 calc R U . . .
N1 N 0.1434(4) 0.2846(4) 0.9090(16) 0.058(2) Uani 1 1 d . . . . .
H1A H 0.129744 0.292210 0.807685 0.069 Uiso 1 1 calc R U . . .
H1B H 0.129298 0.290600 1.011761 0.069 Uiso 1 1 calc R U . . .
N2 N 0.2060(5) 0.2553(6) 0.7625(14) 0.064(3) Uani 1 1 d . . . . .
H2A H 0.193255 0.262487 0.659012 0.077 Uiso 1 1 calc R U . . .
H2B H 0.233740 0.241736 0.765559 0.077 Uiso 1 1 calc R U . . .
N3 N 0.2068(6) 0.2547(5) 1.0711(11) 0.057(3) Uani 1 1 d . . . . .
H3A H 0.235489 0.242234 1.072381 0.068 Uiso 1 1 calc R U . . .
H3B H 0.192196 0.260973 1.172531 0.068 Uiso 1 1 calc R U . . .
C9 C 0.1844(5) 0.2646(6) 0.9068(17) 0.058(3) Uani 1 1 d . . . . .
O4 O 0.4309(5) 0.5250(5) 0.4993(14) 0.064(3) Uani 0.866(13) 1 d . . P A 1
C10 C 0.4234(6) 0.4863(6) 0.381(2) 0.051(4) Uani 0.866(13) 1 d . . P A 1
C11 C 0.3870(6) 0.4787(6) 0.211(2) 0.050(3) Uani 0.866(13) 1 d . . P A 1
H11 H 0.370077 0.506405 0.192401 0.060 Uiso 0.866(13) 1 calc R U P A 1
C12 C 0.3771(6) 0.4368(6) 0.087(2) 0.054(4) Uani 0.866(13) 1 d . . P A 1
C13 C 0.3979(7) 0.3881(7) 0.113(2) 0.062(4) Uani 0.866(13) 1 d . . P A 1
H13A H 0.436271 0.400608 0.038013 0.075 Uiso 0.866(13) 1 calc R U P A 1
H13B H 0.363481 0.346226 0.068731 0.075 Uiso 0.866(13) 1 calc R U P A 1
C14 C 0.4139(6) 0.3796(6) 0.3078(17) 0.046(3) Uani 0.866(13) 1 d . . P A 1
C15 C 0.4525(6) 0.4447(6) 0.3922(18) 0.049(3) Uani 0.866(13) 1 d . . P A 1
H15A H 0.459286 0.439017 0.520087 0.059 Uiso 0.866(13) 1 calc R U P A 1
H15B H 0.495088 0.467181 0.334039 0.059 Uiso 0.866(13) 1 calc R U P A 1
C16 C 0.3415(7) 0.4302(7) -0.079(3) 0.073(4) Uani 0.866(13) 1 d . . P A 1
H16A H 0.300043 0.390419 -0.075255 0.109 Uiso 0.866(13) 1 calc R U P A 1
H16B H 0.366257 0.428939 -0.181887 0.109 Uiso 0.866(13) 1 calc R U P A 1
H16C H 0.334610 0.466751 -0.091690 0.109 Uiso 0.866(13) 1 calc R U P A 1
C17 C 0.3504(5) 0.3404(6) 0.418(3) 0.063(4) Uani 0.866(13) 1 d . . P A 1
H17A H 0.313603 0.331476 0.342733 0.095 Uiso 0.866(13) 1 calc R U P A 1
H17B H 0.351343 0.365385 0.522869 0.095 Uiso 0.866(13) 1 calc R U P A 1
H17C H 0.346718 0.299928 0.457869 0.095 Uiso 0.866(13) 1 calc R U P A 1
C18 C 0.4506(7) 0.3413(7) 0.3100(19) 0.061(4) Uani 0.866(13) 1 d . . P A 1
H18A H 0.425489 0.300698 0.245781 0.091 Uiso 0.866(13) 1 calc R U P A 1
H18B H 0.457027 0.332491 0.434162 0.091 Uiso 0.866(13) 1 calc R U P A 1
H18C H 0.492319 0.366610 0.251474 0.091 Uiso 0.866(13) 1 calc R U P A 1
F1 F 0.6048(7) 0.4002(7) 0.434(3) 0.104(6) Uani 0.59(2) 1 d . U P B 1
F2 F 0.7328(8) 0.4620(8) 0.433(3) 0.111(6) Uani 0.59(2) 1 d . U P B 1
C1F C 0.6334(9) 0.3658(11) 0.441(4) 0.073(6) Uani 0.59(2) 1 d D U P B 1
C2F C 0.6995(9) 0.3987(10) 0.432(4) 0.073(6) Uani 0.59(2) 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 0.00 0.0250
0.00 -1.00 0.00 0.0300
1.00 0.00 0.00 0.0230
-1.00 0.00 0.00 0.0690
1.00 -1.00 0.00 0.0310
-1.00 1.00 0.00 0.0610
0.00 0.00 1.00 0.1990
0.00 0.00 -1.00 0.1790
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(5) . .
O2 S1 O3 112.7(5) . .
O1 S1 O3 112.4(4) . .
O2 S1 C6 106.0(4) . .
O1 S1 C6 107.1(5) . .
O3 S1 C6 105.5(5) . .
C2 C1 C2 120.8(10) 3_565 .
C2 C1 C3 119.2(9) 3_565 .
C2 C1 C3 119.9(9) . .
C1 C2 C1 119.2(10) 2_665 .
C1 C2 H2 120.4 2_665 .
C1 C2 H2 120.4 . .
C8 C3 C4 117.5(9) . .
C8 C3 C1 121.5(9) . .
C4 C3 C1 120.8(9) . .
C5 C4 C3 121.2(10) . .
C5 C4 H4 119.4 . .
C3 C4 H4 119.4 . .
C4 C5 C6 120.7(10) . .
C4 C5 H5 119.6 . .
C6 C5 H5 119.6 . .
C7 C6 C5 120.6(10) . .
C7 C6 S1 119.1(8) . .
C5 C6 S1 120.2(8) . .
C6 C7 C8 118.6(10) . .
C6 C7 H7 120.7 . .
C8 C7 H7 120.7 . .
C3 C8 C7 121.3(10) . .
C3 C8 H8 119.4 . .
C7 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 122.2(12) . .
N2 C9 N3 119.1(9) . .
N1 C9 N3 118.7(11) . .
O4 C10 C15 121.9(13) . .
O4 C10 C11 123.8(11) . .
C15 C10 C11 114.3(12) . .
C12 C11 C10 124.4(12) . .
C12 C11 H11 117.8 . .
C10 C11 H11 117.8 . .
C11 C12 C16 123.7(13) . .
C11 C12 C13 120.9(13) . .
C16 C12 C13 115.3(13) . .
C12 C13 C14 115.3(13) . .
C12 C13 H13A 108.4 . .
C14 C13 H13A 108.4 . .
C12 C13 H13B 108.4 . .
C14 C13 H13B 108.4 . .
H13A C13 H13B 107.5 . .
C15 C14 C13 108.6(11) . .
C15 C14 C18 112.0(11) . .
C13 C14 C18 109.9(10) . .
C15 C14 C17 108.4(10) . .
C13 C14 C17 110.0(12) . .
C18 C14 C17 107.9(10) . .
C10 C15 C14 115.2(10) . .
C10 C15 H15A 108.5 . .
C14 C15 H15A 108.5 . .
C10 C15 H15B 108.5 . .
C14 C15 H15B 108.5 . .
H15A C15 H15B 107.5 . .
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 123(2) . 2_655
F1 C1F C2F 117(2) . .
C2F C1F C2F 119(2) 2_655 .
F2 C2F C1F 118(2) . 3_665
F2 C2F C1F 122(2) . .
C1F C2F C1F 120(2) 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 1.421(7) .
S1 O1 1.446(8) .
S1 O3 1.471(9) .
S1 C6 1.788(11) .
C1 C2 1.415(15) 3_565
C1 C2 1.421(15) .
C1 C3 1.476(14) .
C2 H2 0.9500 .
C3 C8 1.357(15) .
C3 C4 1.456(15) .
C4 C5 1.320(17) .
C4 H4 0.9500 .
C5 C6 1.389(16) .
C5 H5 0.9500 .
C6 C7 1.380(15) .
C7 C8 1.417(16) .
C7 H7 0.9500 .
C8 H8 0.9500 .
N1 C9 1.299(13) .
N1 H1A 0.8800 .
N1 H1B 0.8800 .
N2 C9 1.263(15) .
N2 H2A 0.8800 .
N2 H2B 0.8800 .
N3 C9 1.408(16) .
N3 H3A 0.8800 .
N3 H3B 0.8800 .
O4 C10 1.231(16) .
C10 C15 1.485(17) .
C10 C11 1.50(2) .
C11 C12 1.30(2) .
C11 H11 0.9500 .
C12 C16 1.47(2) .
C12 C13 1.502(19) .
C13 C14 1.54(2) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.506(18) .
C14 C18 1.566(19) .
C14 C17 1.571(19) .
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 1.32(2) .
F2 C2F 1.32(2) .
C1F C2F 1.36(3) 2_655
C1F C2F 1.381(13) .
