#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:44:41 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179024 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/22/4122299.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_4122299
loop_
_publ_author_name
'Zhao, Yanchuan'
'Markopoulos, Georgios'
'Swager, Timothy M.'
_publ_section_title
;
 (19)F NMR fingerprints: identification of neutral organic compounds in a
 molecular container.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10683
_journal_page_last               10690
_journal_paper_doi               10.1021/ja504110f
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C53 H40 F6 N2 O6 W'
_chemical_formula_weight         1098.72
_chemical_name_systematic
; 
 ? 
;
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 120.7920(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.0206(5)
_cell_length_b                   16.0491(4)
_cell_length_c                   14.6836(4)
_cell_measurement_reflns_used    9681
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.28
_cell_measurement_theta_min      2.71
_cell_volume                     4255.37(19)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0083
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            240360
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.576
_diffrn_reflns_theta_min         1.698
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    2.799
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.999
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         7749
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0147
_refine_ls_R_factor_gt           0.0142
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[σ²(Fo²)+(0.0193P)²+5.2359P] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0380
_refine_ls_wR_factor_ref         0.0382
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7564
_reflns_number_total             7749
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja504110f_si_002.cif
_cod_data_source_block           x14010
_cod_depositor_comments
'Adding full bibliography for 4122297--4122300.cif.'
_cod_database_code               4122299
#BEGIN Tags that were not found in dictionaries:
_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   0.559
_shelx_estimated_absorpt_t_max   0.721
_shelxl_version_number           2012-9
#END Tags that were not found in dictionaries
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
W1 W 1.0000 0.82508(2) 0.7500 0.01034(2) Uani 1 2 d S TU P . .
N2 N 1.0000 0.68115(8) 0.7500 0.0126(2) Uani 1 2 d S TU P A .
C47 C 1.0000 0.61059(10) 0.7500 0.0152(3) Uani 1 2 d S TU P . .
C48 C 0.9970(18) 0.52019(16) 0.750(2) 0.0386(16) Uani 0.5 1 d . U P A -1
H48A H 0.9513 0.5011 0.6875 0.058 Uiso 0.5 1 calc R U P A -1
H48B H 0.9978 0.5013 0.8143 0.058 Uiso 0.5 1 calc R U P A -1
H48C H 1.0398 0.4973 0.7493 0.058 Uiso 0.5 1 calc R U P A -1
O1 O 0.90142(4) 0.80744(5) 0.62925(6) 0.01293(13) Uani 1 1 d . . . . .
O2 O 1.04069(4) 0.80852(5) 0.65789(6) 0.01297(13) Uani 1 1 d . . . . .
C11 C 0.86388(5) 0.73644(6) 0.58107(8) 0.01155(16) Uani 1 1 d . . . . .
C12 C 0.82055(5) 0.69732(7) 0.61631(8) 0.01172(16) Uani 1 1 d . . . . .
C13 C 0.78139(6) 0.62568(7) 0.56394(8) 0.01276(17) Uani 1 1 d . . . . .
H13 H 0.7517 0.5988 0.5868 0.015 Uiso 1 1 calc R U . . .
C14 C 0.78488(6) 0.59259(7) 0.47844(8) 0.01245(17) Uani 1 1 d . . . . .
C15 C 0.82890(6) 0.63264(7) 0.44608(8) 0.01299(17) Uani 1 1 d . . . . .
H15 H 0.8314 0.6107 0.3879 0.016 Uiso 1 1 calc R U . . .
C16 C 0.86938(5) 0.70403(7) 0.49677(8) 0.01205(17) Uani 1 1 d . . . . .
C17 C 0.92200(6) 0.74144(7) 0.46594(8) 0.01349(17) Uani 1 1 d . . . . .
H17A H 0.9266 0.8021 0.4803 0.016 Uiso 1 1 calc R U . . .
H17B H 0.9016 0.7334 0.3890 0.016 Uiso 1 1 calc R U . . .
C21 C 1.05408(6) 0.73566(7) 0.62301(8) 0.01167(16) Uani 1 1 d . . . . .
C22 C 0.99800(6) 0.70115(7) 0.52749(8) 0.01229(17) Uani 1 1 d . . . . .
C23 C 1.01195(6) 0.62564(7) 0.49375(8) 0.01481(18) Uani 1 1 d . . . . .
H23 H 0.9744 0.6013 0.4295 0.018 Uiso 1 1 calc R U . . .
C24 C 1.07986(6) 0.58545(7) 0.55256(9) 0.01630(19) Uani 1 1 d . . . . .
H24 H 1.0887 0.5343 0.5284 0.020 Uiso 1 1 calc R U . . .
C25 C 1.13467(6) 0.62069(7) 0.64703(9) 0.01444(18) Uani 1 1 d . . . . .
H25 H 1.1810 0.5931 0.6871 0.017 Uiso 1 1 calc R U . . .
C26 C 1.12293(6) 0.69578(7) 0.68407(8) 0.01219(16) Uani 1 1 d . . . . .
C27 C 1.18242(6) 0.73124(7) 0.78947(8) 0.01290(17) Uani 1 1 d . . . . .
H27A H 1.1771 0.7926 0.7877 0.015 Uiso 1 1 calc R U . . .
H27B H 1.2316 0.7186 0.7991 0.015 Uiso 1 1 calc R U . . .
C31 C 0.74420(6) 0.51623(7) 0.42043(8) 0.01260(17) Uani 1 1 d . . . . .
C32 C 0.69357(6) 0.51799(7) 0.31116(9) 0.01571(18) Uani 1 1 d . . . . .
H32 H 0.6823 0.5697 0.2747 0.019 Uiso 1 1 calc R U . . .
C33 C 0.65932(6) 0.44597(8) 0.25464(9) 0.01662(19) Uani 1 1 d . . . . .
H33 H 0.6250 0.4490 0.1806 0.020 Uiso 1 1 calc R U . . .
C34 C 0.67519(7) 0.36994(8) 0.30611(9) 0.0182(2) Uani 1 1 d . . . . .
H34 H 0.6514 0.3208 0.2676 0.022 Uiso 1 1 calc R U . . .
C35 C 0.72612(7) 0.36562(8) 0.41442(10) 0.0196(2) Uani 1 1 d . . . . .
H35 H 0.7383 0.3136 0.4503 0.023 Uiso 1 1 calc R U . . .
C36 C 0.75876(6) 0.43836(7) 0.46901(8) 0.01520(18) Uani 1 1 d . . . . .
O3 O 0.81612(5) 0.43434(6) 0.57724(7) 0.01904(16) Uani 1 1 d . . . . .
C37 C 0.79814(8) 0.40890(9) 0.64749(10) 0.0219(2) Uani 1 1 d . . . . .
F1 F 0.73809(6) 0.44622(7) 0.63632(8) 0.0356(2) Uani 1 1 d . . . . .
F2 F 0.85435(5) 0.42735(7) 0.74341(6) 0.0333(2) Uani 1 1 d . . . . .
F3 F 0.78643(9) 0.32771(6) 0.64623(9) 0.0454(3) Uani 1 1 d . . . . .
N1 N 1.0000 0.93364(8) 0.7500 0.0129(2) Uani 1 2 d S T P . .
C41 C 1.0000 1.01953(9) 0.7500 0.0124(2) Uani 1 2 d S T P . .
C42 C 1.03110(6) 1.06214(7) 0.84726(9) 0.01471(18) Uani 1 1 d . . . . .
C43 C 1.02963(7) 1.14876(8) 0.84498(10) 0.0193(2) Uani 1 1 d . . . . .
H43 H 1.0493 1.1786 0.9098 0.023 Uiso 1 1 calc R U . . .
C44 C 1.0000 1.19292(11) 0.7500 0.0214(3) Uani 1 2 d S T P . .
C45 C 1.06541(7) 1.01412(8) 0.94939(9) 0.0204(2) Uani 1 1 d . . . . .
H45A H 1.1098 0.9853 0.9601 0.031 Uiso 1 1 calc R U . . .
H45B H 1.0298 0.9731 0.9463 0.031 Uiso 1 1 calc R U . . .
H45C H 1.0790 1.0526 1.0084 0.031 Uiso 1 1 calc R U . . .
C46 C 1.0000 1.28674(12) 0.7500 0.0346(5) Uani 1 2 d S T P . .
H46A H 1.0465 1.3071 0.7577 0.052 Uiso 0.5 1 calc R U P B -1
H46B H 0.9953 1.3071 0.8092 0.052 Uiso 0.5 1 calc R U P B -1
H46C H 0.9582 1.3071 0.6831 0.052 Uiso 0.5 1 calc R 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'
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'
W W -0.8490 6.8722 '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
N1 W1 O1 98.40(2) . 2_756
N1 W1 O1 98.40(2) . .
O1 W1 O1 163.20(5) 2_756 .
N1 W1 O2 97.82(2) . 2_756
O1 W1 O2 89.36(3) 2_756 2_756
O1 W1 O2 88.37(3) . 2_756
N1 W1 O2 97.82(2) . .
O1 W1 O2 88.37(3) 2_756 .
O1 W1 O2 89.36(3) . .
O2 W1 O2 164.36(5) 2_756 .
N1 W1 N2 180.0 . .
O1 W1 N2 81.60(2) 2_756 .
O1 W1 N2 81.60(2) . .
O2 W1 N2 82.18(2) 2_756 .
O2 W1 N2 82.18(2) . .
C47 N2 W1 180.0 . .
N2 C47 C48 177.4(13) . .
C47 C48 H48A 109.5 . .
C47 C48 H48B 109.5 . .
H48A C48 H48B 109.5 . .
C47 C48 H48C 109.5 . .
H48A C48 H48C 109.5 . .
H48B C48 H48C 109.5 . .
C11 O1 W1 131.46(7) . .
C21 O2 W1 128.68(7) . .
O1 C11 C16 118.84(9) . .
O1 C11 C12 119.72(9) . .
C16 C11 C12 121.44(10) . .
C13 C12 C11 118.46(10) . .
C13 C12 C27 120.70(9) . 2_756
C11 C12 C27 120.82(9) . 2_756
C12 C13 C14 121.38(10) . .
C12 C13 H13 119.3 . .
C14 C13 H13 119.3 . .
C15 C14 C13 118.64(10) . .
C15 C14 C31 118.14(9) . .
C13 C14 C31 123.21(10) . .
C16 C15 C14 121.81(10) . .
C16 C15 H15 119.1 . .
C14 C15 H15 119.1 . .
C15 C16 C11 118.24(10) . .
C15 C16 C17 120.34(9) . .
C11 C16 C17 121.28(9) . .
C16 C17 C22 111.06(8) . .
C16 C17 H17A 109.4 . .
C22 C17 H17A 109.4 . .
C16 C17 H17B 109.4 . .
C22 C17 H17B 109.4 . .
H17A C17 H17B 108.0 . .
O2 C21 C22 118.99(9) . .
O2 C21 C26 119.60(9) . .
C22 C21 C26 121.39(10) . .
C23 C22 C21 118.39(10) . .
C23 C22 C17 120.41(9) . .
C21 C22 C17 121.06(10) . .
C24 C23 C22 121.14(10) . .
C24 C23 H23 119.4 . .
C22 C23 H23 119.4 . .
C25 C24 C23 119.54(10) . .
C25 C24 H24 120.2 . .
C23 C24 H24 120.2 . .
C24 C25 C26 121.23(10) . .
C24 C25 H25 119.4 . .
C26 C25 H25 119.4 . .
C25 C26 C21 118.30(10) . .
C25 C26 C27 120.25(9) . .
C21 C26 C27 121.42(10) . .
C26 C27 C12 113.48(9) . 2_756
C26 C27 H27A 108.9 . .
C12 C27 H27A 108.9 2_756 .
C26 C27 H27B 108.9 . .
C12 C27 H27B 108.9 2_756 .
H27A C27 H27B 107.7 . .
C36 C31 C32 116.34(10) . .
C36 C31 C14 122.31(9) . .
C32 C31 C14 121.11(10) . .
C33 C32 C31 121.68(11) . .
C33 C32 H32 119.2 . .
C31 C32 H32 119.2 . .
C34 C33 C32 120.07(10) . .
C34 C33 H33 120.0 . .
C32 C33 H33 120.0 . .
C33 C34 C35 119.84(11) . .
C33 C34 H34 120.1 . .
C35 C34 H34 120.1 . .
C36 C35 C34 118.90(11) . .
C36 C35 H35 120.5 . .
C34 C35 H35 120.5 . .
C35 C36 C31 123.14(10) . .
C35 C36 O3 119.65(10) . .
C31 C36 O3 116.83(10) . .
C37 O3 C36 117.72(10) . .
F3 C37 F2 106.99(12) . .
F3 C37 F1 106.47(13) . .
F2 C37 F1 107.67(11) . .
F3 C37 O3 114.55(12) . .
F2 C37 O3 107.58(11) . .
F1 C37 O3 113.24(11) . .
C41 N1 W1 180.0 . .
N1 C41 C42 119.09(7) . 2_756
N1 C41 C42 119.09(7) . .
C42 C41 C42 121.83(14) 2_756 .
C43 C42 C41 117.94(11) . .
C43 C42 C45 122.03(11) . .
C41 C42 C45 120.02(11) . .
C42 C43 C44 121.67(12) . .
C42 C43 H43 119.2 . .
C44 C43 H43 119.2 . .
C43 C44 C43 118.92(16) . 2_756
C43 C44 C46 120.54(8) . .
C43 C44 C46 120.54(8) 2_756 .
C42 C45 H45A 109.5 . .
C42 C45 H45B 109.5 . .
H45A C45 H45B 109.5 . .
C42 C45 H45C 109.5 . .
H45A C45 H45C 109.5 . .
H45B C45 H45C 109.5 . .
C44 C46 H46A 109.5 . .
C44 C46 H46B 109.5 . .
H46A C46 H46B 109.5 . .
C44 C46 H46C 109.5 . .
H46A C46 H46C 109.5 . .
H46B C46 H46C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
W1 N1 1.7423(13) .
W1 O1 1.9381(8) 2_756
W1 O1 1.9381(8) .
W1 O2 1.9534(8) 2_756
W1 O2 1.9534(8) .
W1 N2 2.3099(13) .
N2 C47 1.133(2) .
C47 C48 1.452(3) .
C48 H48A 0.9800 .
C48 H48B 0.9800 .
C48 H48C 0.9800 .
O1 C11 1.3600(13) .
O2 C21 1.3625(13) .
C11 C16 1.4009(15) .
C11 C12 1.4052(15) .
C12 C13 1.3937(15) .
C12 C27 1.5176(15) 2_756
C13 C14 1.3992(15) .
C13 H13 0.9500 .
C14 C15 1.3948(15) .
C14 C31 1.4876(15) .
C15 C16 1.3936(15) .
C15 H15 0.9500 .
C16 C17 1.5171(15) .
C17 C22 1.5194(15) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C21 C22 1.4039(14) .
C21 C26 1.4069(14) .
C22 C23 1.3960(15) .
C23 C24 1.3920(16) .
C23 H23 0.9500 .
C24 C25 1.3910(16) .
C24 H24 0.9500 .
C25 C26 1.3952(15) .
C25 H25 0.9500 .
C26 C27 1.5171(15) .
C27 C12 1.5175(15) 2_756
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C31 C36 1.3932(15) .
C31 C32 1.3998(15) .
C32 C33 1.3897(16) .
C32 H32 0.9500 .
C33 C34 1.3832(17) .
C33 H33 0.9500 .
C34 C35 1.3917(17) .
C34 H34 0.9500 .
C35 C36 1.3832(16) .
C35 H35 0.9500 .
C36 O3 1.4219(14) .
O3 C37 1.3314(15) .
C37 F3 1.3246(16) .
C37 F2 1.3280(15) .
C37 F1 1.3294(17) .
N1 C41 1.3785(19) .
C41 C42 1.4066(13) 2_756
C41 C42 1.4066(13) .
C42 C43 1.3905(16) .
C42 C45 1.5019(17) .
C43 C44 1.3951(16) .
C43 H43 0.9500 .
C44 C43 1.3951(16) 2_756
C44 C46 1.506(3) .
C45 H45A 0.9800 .
C45 H45B 0.9800 .
C45 H45C 0.9800 .
C46 H46A 0.9800 .
C46 H46B 0.9800 .
C46 H46C 0.9800 .
