#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:49:03 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179025 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/23/4122300.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_4122300
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 O4 W'
_chemical_formula_weight         1066.72
_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                 120.9240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.4476(7)
_cell_length_b                   15.8488(5)
_cell_length_c                   14.2263(5)
_cell_measurement_reflns_used    9739
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.65
_cell_measurement_theta_min      2.57
_cell_volume                     4148.4(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0287
_diffrn_reflns_av_unetI/netI     0.0088
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            160651
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.506
_diffrn_reflns_theta_min         1.696
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    2.865
_exptl_absorpt_correction_T_max  0.3380
_exptl_absorpt_correction_T_min  0.2990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         1.399
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         6904
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0171
_refine_ls_R_factor_gt           0.0165
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[σ²(Fo²)+(0.0201P)²+4.8346P] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0425
_refine_ls_wR_factor_ref         0.0428
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6770
_reflns_number_total             6904
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja504110f_si_003.cif
_cod_data_source_block           x14009
_cod_depositor_comments
'Adding full bibliography for 4122297--4122300.cif.'
_cod_database_code               4122300
#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   0.612
_shelx_estimated_absorpt_t_max   0.690
_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 0.82569(2) 0.7500 0.01829(2) Uani 1 2 d S TU P . .
N2 N 1.0000 0.68135(10) 0.7500 0.0194(3) Uani 1 2 d S TU P A .
C47 C 1.0000 0.61075(12) 0.7500 0.0188(3) Uani 1 2 d S TU P . .
C48 C 0.99670(19) 0.52151(18) 0.7200(2) 0.0280(6) Uani 0.5 1 d . U P A -1
H48A H 0.9466 0.5068 0.6645 0.042 Uiso 0.5 1 calc R U P A -1
H48B H 1.0128 0.4863 0.7851 0.042 Uiso 0.5 1 calc R U P A -1
H48C H 1.0285 0.5119 0.6905 0.042 Uiso 0.5 1 calc R U P A -1
O1 O 0.90122(5) 0.80777(6) 0.62973(8) 0.02073(18) Uani 1 1 d . . . . .
O2 O 1.03446(5) 0.80900(6) 0.64842(8) 0.02079(18) Uani 1 1 d . . . . .
C11 C 0.86338(7) 0.73536(8) 0.58448(11) 0.0183(2) Uani 1 1 d . . . . .
C12 C 0.82177(7) 0.69995(8) 0.62492(11) 0.0185(2) Uani 1 1 d . . . . .
C13 C 0.78239(7) 0.62646(8) 0.57614(11) 0.0188(2) Uani 1 1 d . . . . .
H13 H 0.7532 0.6028 0.6018 0.023 Uiso 1 1 calc R U . . .
C14 C 0.78494(7) 0.58692(8) 0.49034(11) 0.0180(2) Uani 1 1 d . . . . .
C15 C 0.82728(7) 0.62385(8) 0.45250(10) 0.0185(2) Uani 1 1 d . . . . .
H15 H 0.8291 0.5978 0.3938 0.022 Uiso 1 1 calc R U . . .
C16 C 0.86689(7) 0.69758(8) 0.49833(11) 0.0183(2) Uani 1 1 d . . . . .
C17 C 0.91499(7) 0.73337(8) 0.45864(11) 0.0204(2) Uani 1 1 d . . . . .
H17A H 0.9182 0.7953 0.4688 0.025 Uiso 1 1 calc R U . . .
H17B H 0.8923 0.7219 0.3793 0.025 Uiso 1 1 calc R U . . .
C21 C 1.04800(7) 0.73557(8) 0.61220(11) 0.0186(2) Uani 1 1 d . . . . .
C22 C 0.99127(7) 0.69646(8) 0.51862(11) 0.0190(2) Uani 1 1 d . . . . .
C23 C 1.00596(8) 0.62087(9) 0.48349(11) 0.0220(2) Uani 1 1 d . . . . .
H23 H 0.9680 0.5930 0.4211 0.026 Uiso 1 1 calc R U . . .
C24 C 1.07518(8) 0.58559(9) 0.53824(12) 0.0245(3) Uani 1 1 d . . . . .
H24 H 1.0845 0.5346 0.5125 0.029 Uiso 1 1 calc R U . . .
C25 C 1.13052(8) 0.62518(9) 0.63056(12) 0.0227(2) Uani 1 1 d . . . . .
H25 H 1.1778 0.6010 0.6675 0.027 Uiso 1 1 calc R U . . .
C26 C 1.11799(7) 0.69998(8) 0.67006(11) 0.0191(2) Uani 1 1 d . . . . .
C27 C 1.17730(7) 0.73819(8) 0.77653(11) 0.0207(2) Uani 1 1 d . . . . .
H27A H 1.1695 0.7998 0.7754 0.025 Uiso 1 1 calc R U . . .
H27B H 1.2250 0.7288 0.7831 0.025 Uiso 1 1 calc R U . . .
C31 C 0.74345(7) 0.50896(8) 0.43412(11) 0.0176(2) Uani 1 1 d . . . . .
C32 C 0.70187(7) 0.51059(8) 0.31937(11) 0.0207(2) Uani 1 1 d . . . . .
H32 H 0.6987 0.5617 0.2823 0.025 Uiso 1 1 calc R U . . .
C33 C 0.66509(8) 0.43994(9) 0.25809(11) 0.0231(2) Uani 1 1 d . . . . .
H33 H 0.6376 0.4432 0.1804 0.028 Uiso 1 1 calc R U . . .
C34 C 0.66838(8) 0.36520(9) 0.30988(12) 0.0242(3) Uani 1 1 d . . . . .
H34 H 0.6439 0.3165 0.2682 0.029 Uiso 1 1 calc R U . . .
C35 C 0.70765(8) 0.36167(9) 0.42330(12) 0.0237(2) Uani 1 1 d . . . . .
H35 H 0.7090 0.3106 0.4593 0.028 Uiso 1 1 calc R U . . .
C36 C 0.74525(7) 0.43216(8) 0.48542(11) 0.0197(2) Uani 1 1 d . . . . .
C37 C 0.78667(9) 0.42119(9) 0.60739(12) 0.0282(3) Uani 1 1 d . . . . .
F1 F 0.75319(7) 0.45665(7) 0.65552(8) 0.0405(2) Uani 1 1 d . . . . .
F2 F 0.85333(6) 0.45519(7) 0.65665(9) 0.0434(3) Uani 1 1 d . . . . .
F3 F 0.79626(8) 0.33987(7) 0.63786(9) 0.0468(3) Uani 1 1 d . . . . .
N1 N 1.0000 0.93551(10) 0.7500 0.0205(3) Uani 1 2 d S T P . .
C41 C 1.0000 1.02239(11) 0.7500 0.0183(3) Uani 1 2 d S T P . .
C42 C 1.03053(7) 1.06568(8) 0.85040(11) 0.0190(2) Uani 1 1 d . . . . .
C43 C 1.02893(8) 1.15334(8) 0.84810(12) 0.0221(2) Uani 1 1 d . . . . .
H43 H 1.0480 1.1836 0.9150 0.026 Uiso 1 1 calc R U . . .
C44 C 1.0000 1.19797(12) 0.7500 0.0242(4) Uani 1 2 d S T P . .
C45 C 1.06582(8) 1.01733(10) 0.95625(12) 0.0264(3) Uani 1 1 d . . . . .
H45A H 1.1106 0.9910 0.9680 0.040 Uiso 1 1 calc R U . . .
H45B H 1.0325 0.9735 0.9529 0.040 Uiso 1 1 calc R U . . .
H45C H 1.0774 1.0559 1.0169 0.040 Uiso 1 1 calc R U . . .
C46 C 1.0000 1.29289(13) 0.7500 0.0362(5) Uani 1 2 d S T P . .
H46A H 1.0013 1.3135 0.6861 0.054 Uiso 0.5 1 calc R U P . .
H46B H 1.0428 1.3135 0.8171 0.054 Uiso 0.5 1 calc R U P . .
H46C H 0.9559 1.3135 0.7468 0.054 Uiso 0.5 1 calc R U 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'
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 98.41(3) . .
N1 W1 O1 98.41(3) . 2_756
O1 W1 O1 163.18(6) . 2_756
N1 W1 O2 97.79(3) . .
O1 W1 O2 89.12(4) . .
O1 W1 O2 88.61(4) 2_756 .
N1 W1 O2 97.79(3) . 2_756
O1 W1 O2 88.61(4) . 2_756
O1 W1 O2 89.12(4) 2_756 2_756
O2 W1 O2 164.41(6) . 2_756
N1 W1 N2 180.0 . .
O1 W1 N2 81.59(3) . .
O1 W1 N2 81.59(3) 2_756 .
O2 W1 N2 82.21(3) . .
O2 W1 N2 82.21(3) 2_756 .
C47 N2 W1 180.0 . .
N2 C47 C48 164.40(12) . .
C11 O1 W1 130.95(8) . .
C21 O2 W1 129.16(8) . .
O1 C11 C16 119.16(12) . .
O1 C11 C12 119.56(12) . .
C16 C11 C12 121.27(11) . .
C13 C12 C11 118.66(12) . .
C13 C12 C27 120.64(12) . 2_756
C11 C12 C27 120.63(11) . 2_756
C12 C13 C14 121.52(12) . .
C13 C14 C15 118.21(11) . .
C13 C14 C31 123.98(12) . .
C15 C14 C31 117.78(11) . .
C16 C15 C14 122.03(12) . .
C15 C16 C11 118.30(12) . .
C15 C16 C17 120.44(12) . .
C11 C16 C17 121.21(12) . .
C16 C17 C22 112.86(10) . .
O2 C21 C22 119.09(12) . .
O2 C21 C26 119.45(12) . .
C22 C21 C26 121.46(12) . .
C23 C22 C21 118.26(12) . .
C23 C22 C17 120.35(12) . .
C21 C22 C17 121.36(12) . .
C24 C23 C22 121.14(13) . .
C25 C24 C23 119.73(13) . .
C24 C25 C26 121.13(13) . .
C25 C26 C21 118.25(13) . .
C25 C26 C27 120.34(12) . .
C21 C26 C27 121.30(12) . .
C26 C27 C12 111.66(10) . 2_756
C32 C31 C36 116.79(12) . .
C32 C31 C14 117.15(12) . .
C36 C31 C14 125.97(12) . .
C33 C32 C31 122.16(13) . .
C34 C33 C32 120.07(13) . .
C33 C34 C35 119.41(13) . .
C34 C35 C36 120.86(13) . .
C35 C36 C31 120.69(12) . .
C35 C36 C37 116.50(12) . .
C31 C36 C37 122.82(12) . .
F2 C37 F3 105.78(14) . .
F2 C37 F1 105.73(13) . .
F3 C37 F1 105.69(14) . .
F2 C37 C36 113.40(13) . .
F3 C37 C36 112.76(12) . .
F1 C37 C36 112.80(13) . .
C41 N1 W1 180.0 . .
N1 C41 C42 119.19(8) . 2_756
N1 C41 C42 119.19(8) . .
C42 C41 C42 121.62(16) 2_756 .
C43 C42 C41 118.08(13) . .
C43 C42 C45 121.81(13) . .
C41 C42 C45 120.07(12) . .
C42 C43 C44 121.58(13) . .
C43 C44 C43 119.02(17) . 2_756
C43 C44 C46 120.49(9) . .
C43 C44 C46 120.49(9) 2_756 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
W1 N1 1.7405(15) .
W1 O1 1.9418(10) .
W1 O1 1.9419(10) 2_756
W1 O2 1.9500(11) .
W1 O2 1.9501(11) 2_756
W1 N2 2.2876(15) .
N2 C47 1.119(2) .
C47 C48 1.468(3) .
O1 C11 1.3613(15) .
O2 C21 1.3631(16) .
C11 C16 1.4003(18) .
C11 C12 1.4036(18) .
C12 C13 1.3961(17) .
C12 C27 1.5182(18) 2_756
C13 C14 1.3979(18) .
C14 C15 1.3998(18) .
C14 C31 1.4923(17) .
C15 C16 1.3939(18) .
C16 C17 1.5177(18) .
C17 C22 1.5205(19) .
C21 C22 1.4044(19) .
C21 C26 1.4068(18) .
C22 C23 1.3950(19) .
C23 C24 1.391(2) .
C24 C25 1.388(2) .
C25 C26 1.3959(19) .
C26 C27 1.5162(19) .
C27 C12 1.5182(18) 2_756
C31 C32 1.4016(18) .
C31 C36 1.4094(18) .
C32 C33 1.3889(18) .
C33 C34 1.377(2) .
C34 C35 1.385(2) .
C35 C36 1.3953(18) .
C36 C37 1.499(2) .
C37 F2 1.340(2) .
C37 F3 1.3415(17) .
C37 F1 1.3437(19) .
N1 C41 1.377(2) .
C41 C42 1.4064(16) 2_756
C41 C42 1.4064(16) .
C42 C43 1.3898(18) .
C42 C45 1.5021(19) .
C43 C44 1.3939(17) .
C44 C43 1.3940(17) 2_756
C44 C46 1.504(3) .
