#------------------------------------------------------------------------------
#$Date: 2019-11-04 12:46:21 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/42/4034236.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_4034236
loop_
_publ_author_name
'Aletti, Anna B.'
'Miljkovic, Ana'
'Toma, Lucio'
'Bruno, Rosaria'
'Armentano, Donatella'
'Gunnlaugsson, Thorfinnur'
'Bergamaschi, Greta'
'Amendola, Valeria'
_publ_section_title
;
 Halide-Controlled Extending-Shrinking Motion of a Covalent Cage.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4221
_journal_page_last               4228
_journal_paper_doi               10.1021/acs.joc.9b00219
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C57 H57 F18 N8 P3'
_chemical_formula_weight         1289.01
_space_group_crystal_system      trigonal
_space_group_IT_number           147
_space_group_name_Hall           '-P 3'
_space_group_name_H-M_alt        'P -3'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   14.6540(13)
_cell_length_b                   14.6540(13)
_cell_length_c                   17.5993(16)
_cell_measurement_reflns_used    8431
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.2
_cell_measurement_theta_min      2.5
_cell_volume                     3272.9(5)
_computing_cell_refinement       'Bruker APEX'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            64671
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.286
_diffrn_reflns_theta_min         1.157
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       hexagonal-prisms
_exptl_crystal_F_000             1324
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.340
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4429
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.3357
_refine_ls_R_factor_gt           0.2496
_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)+(0.6000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.6483
_refine_ls_wR_factor_ref         0.7363
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1885
_reflns_number_total             4429
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b00219_si_005.cif
_cod_data_source_block           1_PF6_RT
_cod_original_cell_volume        3272.9(7)
_cod_database_code               4034236
_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.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
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
N1 N 0.6667 0.3333 0.4131(6) 0.092(3) Uani 1 3 d S T P
N2 N 0.6667 0.3333 0.0856(7) 0.099(3) Uani 1 3 d S T P
N3 N 0.723(2) 0.7765(17) 0.3105(8) 0.221(9) Uani 1 1 d . . .
N4 N 0.721(2) 0.7771(16) 0.1892(7) 0.207(8) Uani 1 1 d . . .
C1 C 0.7294(17) 0.4359(14) 0.3916(7) 0.212(9) Uani 1 1 d D . .
H1A H 0.7283 0.4408 0.3367 0.255 Uiso 1 1 calc R U .
H1B H 0.8014 0.4598 0.4071 0.255 Uiso 1 1 calc R U .
C2 C 0.6912(13) 0.5096(11) 0.4283(6) 0.156(5) Uani 1 1 d D . .
C3 C 0.6633(11) 0.4970(13) 0.5041(6) 0.153(5) Uani 1 1 d . . .
H3 H 0.6507 0.4359 0.5292 0.184 Uiso 1 1 calc R U .
C4 C 0.6534(10) 0.5753(14) 0.5445(7) 0.149(5) Uani 1 1 d . . .
H4 H 0.6392 0.5680 0.5963 0.179 Uiso 1 1 calc R U .
C5 C 0.6654(13) 0.6625(16) 0.5058(8) 0.168(6) Uani 1 1 d . . .
H5 H 0.6582 0.7134 0.5324 0.202 Uiso 1 1 calc R U .
C6 C 0.6871(11) 0.6769(13) 0.4306(6) 0.145(5) Uani 1 1 d . . .
C7 C 0.6934(16) 0.5945(15) 0.3923(6) 0.170(6) Uani 1 1 d . . .
H7 H 0.6994 0.5982 0.3397 0.204 Uiso 1 1 calc R U .
C8 C 0.694(3) 0.770(3) 0.3905(10) 0.245(12) Uani 1 1 d . . .
H8A H 0.6259 0.7666 0.3939 0.294 Uiso 1 1 calc R U .
H8B H 0.7451 0.8340 0.4162 0.294 Uiso 1 1 calc R U .
C9 C 0.670(2) 0.764(2) 0.2530(14) 0.246(11) Uani 1 1 d . . .
H9 H 0.6002 0.7471 0.2547 0.295 Uiso 1 1 calc R U .
C10 C 0.831(3) 0.819(2) 0.2856(11) 0.217(10) Uani 1 1 d . . .
H10 H 0.8908 0.8408 0.3152 0.260 Uiso 1 1 calc R U .
C11 C 0.825(3) 0.8201(19) 0.2140(12) 0.213(10) Uani 1 1 d . . .
H11 H 0.8826 0.8464 0.1816 0.256 Uiso 1 1 calc R U .
C12 C 0.690(2) 0.769(2) 0.1078(9) 0.222(10) Uani 1 1 d . . .
H12A H 0.6197 0.7606 0.1046 0.267 Uiso 1 1 calc R U .
H12B H 0.7381 0.8342 0.0817 0.267 Uiso 1 1 calc R U .
C13 C 0.6902(12) 0.6802(14) 0.0703(6) 0.157(5) Uani 1 1 d . . .
C14 C 0.6631(11) 0.6611(16) -0.0055(8) 0.167(7) Uani 1 1 d . . .
H14 H 0.6504 0.7088 -0.0315 0.200 Uiso 1 1 calc R U .
C15 C 0.6536(10) 0.5745(14) -0.0453(7) 0.144(4) Uani 1 1 d . . .
H15 H 0.6436 0.5694 -0.0976 0.173 Uiso 1 1 calc R U .
C16 C 0.6595(12) 0.4947(11) -0.0041(6) 0.151(5) Uani 1 1 d . . .
H16 H 0.6420 0.4310 -0.0273 0.181 Uiso 1 1 calc R U .
C17 C 0.6926(13) 0.5130(11) 0.0730(6) 0.150(5) Uani 1 1 d D . .
C18 C 0.6880(13) 0.5918(12) 0.1084(6) 0.147(5) Uani 1 1 d . . .
H18 H 0.6831 0.5892 0.1611 0.176 Uiso 1 1 calc R U .
C19 C 0.7330(16) 0.4407(15) 0.1099(8) 0.203(8) Uani 1 1 d D . .
H19A H 0.8052 0.4653 0.0945 0.244 Uiso 1 1 calc R U .
H19B H 0.7313 0.4447 0.1649 0.244 Uiso 1 1 calc R U .
P1 P 0.9660(6) 0.6353(7) 0.2496(3) 0.151(3) Uani 0.5 1 d . . P
F1 F 1.0841(16) 0.6775(13) 0.2501(17) 0.243(12) Uani 0.5 1 d . . P
F2 F 0.9434(15) 0.5517(19) 0.3117(12) 0.210(9) Uani 0.5 1 d . . P
F3 F 0.942(2) 0.546(2) 0.198(2) 0.33(2) Uani 0.5 1 d . . P
F4 F 0.985(3) 0.7196(16) 0.3032(15) 0.242(11) Uani 0.5 1 d . . P
F5 F 0.991(2) 0.7216(16) 0.1932(15) 0.215(8) Uani 0.5 1 d . . P
F6 F 0.8352(17) 0.6001(16) 0.2477(10) 0.190(6) Uani 0.5 1 d . . P
P2 P 0.0000 0.0000 0.0000 0.195(5) Uani 1 6 d S T P
F7 F 0.0961(16) 0.0765(16) 0.0436(10) 0.307(8) Uani 1 1 d . . .
P3 P 0.0000 0.0000 0.5000 0.202(6) Uani 1 6 d S T P
F8 F 0.0968(15) 0.0720(13) 0.4503(9) 0.293(8) Uani 1 1 d . . .
P4 P 0.3333 0.6667 0.2496(6) 0.207(8) Uani 0.5 3 d S T P
F9 F 0.356(6) 0.760(3) 0.1942(11) 0.41(3) Uani 0.5 1 d . . P
F10 F 0.432(5) 0.713(7) 0.304(2) 0.50(6) Uani 0.5 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
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
C1 N1 C1 112.6(6) 3_665 2_655
C1 N1 C1 112.6(6) 3_665 .
C1 N1 C1 112.6(6) 2_655 .
C19 N2 C19 111.5(7) . 3_665
C19 N2 C19 111.5(7) . 2_655
C19 N2 C19 111.5(7) 3_665 2_655
C9 N3 C10 106(2) . .
C9 N3 C8 130(3) . .
C10 N3 C8 123(2) . .
C9 N4 C11 102.1(18) . .
C9 N4 C12 133(2) . .
C11 N4 C12 124(2) . .
N1 C1 C2 111.4(12) . .
C7 C2 C3 115.8(11) . .
C7 C2 C1 124.8(11) . .
C3 C2 C1 119.1(12) . .
C2 C3 C4 121.4(14) . .
C5 C4 C3 119.0(12) . .
C6 C5 C4 122.6(13) . .
C5 C6 C7 116.1(14) . .
C5 C6 C8 120.4(12) . .
C7 C6 C8 123.2(12) . .
C2 C7 C6 124.3(10) . .
N3 C8 C6 113.2(13) . .
N3 C9 N4 114(2) . .
C11 C10 N3 104(3) . .
C10 C11 N4 112(3) . .
C13 C12 N4 111.0(11) . .
C14 C13 C18 113.1(14) . .
C14 C13 C12 119.0(11) . .
C18 C13 C12 125.7(12) . .
C13 C14 C15 123.9(11) . .
C14 C15 C16 118.4(11) . .
C15 C16 C17 119.3(13) . .
C18 C17 C16 116.6(11) . .
C18 C17 C19 125.4(10) . .
C16 C17 C19 118.1(12) . .
C17 C18 C13 124.6(10) . .
N2 C19 C17 109.5(12) . .
F4 P1 F3 176.9(17) . .
F4 P1 F5 81.6(16) . .
F3 P1 F5 101(2) . .
F4 P1 F1 87.4(17) . .
F3 P1 F1 94.5(16) . .
F5 P1 F1 84.9(14) . .
F4 P1 F2 95.0(15) . .
F3 P1 F2 82(2) . .
F5 P1 F2 176.4(15) . .
F1 P1 F2 93.8(12) . .
F4 P1 F6 88.9(16) . .
F3 P1 F6 89.4(15) . .
F5 P1 F6 90.5(12) . .
F1 P1 F6 174.4(12) . .
F2 P1 F6 90.6(10) . .
F7 P2 F7 180.0 . 4
F7 P2 F7 83.8(10) . 6
F7 P2 F7 96.2(10) 4 6
F7 P2 F7 96.2(10) . 3
F7 P2 F7 83.8(10) 4 3
F7 P2 F7 180(2) 6 3
F7 P2 F7 96.2(10) . 2
F7 P2 F7 83.8(10) 4 2
F7 P2 F7 83.8(10) 6 2
F7 P2 F7 96.2(10) 3 2
F7 P2 F7 83.8(10) . 5
F7 P2 F7 96.2(10) 4 5
F7 P2 F7 96.2(10) 6 5
F7 P2 F7 83.8(10) 3 5
F7 P2 F7 180.0(17) 2 5
F8 P3 F8 88.8(10) . 6_556
F8 P3 F8 91.2(10) . 3
F8 P3 F8 180.0(10) 6_556 3
F8 P3 F8 91.2(10) . 2
F8 P3 F8 88.8(10) 6_556 2
F8 P3 F8 91.2(10) 3 2
F8 P3 F8 88.8(10) . 5_556
F8 P3 F8 91.2(10) 6_556 5_556
F8 P3 F8 88.8(10) 3 5_556
F8 P3 F8 180.0(10) 2 5_556
F8 P3 F8 180.0 . 4_556
F8 P3 F8 91.2(10) 6_556 4_556
F8 P3 F8 88.8(10) 3 4_556
F8 P3 F8 88.8(10) 2 4_556
F8 P3 F8 91.2(10) 5_556 4_556
F9 P4 F9 85.4(17) 3_565 .
F9 P4 F9 85.4(17) 3_565 2_665
F9 P4 F9 85.4(17) . 2_665
F9 P4 F10 166(5) 3_565 2_665
F9 P4 F10 85(3) . 2_665
F9 P4 F10 104(4) 2_665 2_665
F9 P4 F10 104(4) 3_565 3_565
F9 P4 F10 166(5) . 3_565
F9 P4 F10 85(3) 2_665 3_565
F10 P4 F10 87(3) 2_665 3_565
F9 P4 F10 85(3) 3_565 .
F9 P4 F10 104(4) . .
F9 P4 F10 166(5) 2_665 .
F10 P4 F10 87(3) 2_665 .
F10 P4 F10 87(3) 3_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.366(18) 3_665
N1 C1 1.366(18) 2_655
N1 C1 1.366(18) .
N2 C19 1.44(2) .
N2 C19 1.44(2) 3_665
N2 C19 1.44(2) 2_655
N3 C9 1.23(2) .
N3 C10 1.45(3) .
N3 C8 1.46(2) .
N4 C9 1.31(2) .
N4 C11 1.39(3) .
N4 C12 1.49(2) .
C1 C2 1.582(17) .
C2 C7 1.382(18) .
C2 C3 1.381(17) .
C3 C4 1.42(2) .
C4 C5 1.38(2) .
C5 C6 1.352(18) .
C6 C7 1.426(17) .
C6 C8 1.50(3) .
C10 C11 1.26(2) .
C12 C13 1.47(2) .
C13 C14 1.380(19) .
C13 C18 1.444(18) .
C14 C15 1.39(2) .
C15 C16 1.41(2) .
C16 C17 1.421(15) .
C17 C18 1.342(16) .
C17 C19 1.590(16) .
P1 F4 1.47(2) .
P1 F3 1.49(2) .
P1 F5 1.502(19) .
P1 F1 1.52(2) .
P1 F2 1.549(19) .
P1 F6 1.72(2) .
P2 F7 1.500(17) .
P2 F7 1.500(17) 4
P2 F7 1.500(17) 6
P2 F7 1.500(17) 3
P2 F7 1.500(17) 2
P2 F7 1.500(17) 5
P3 F8 1.548(16) .
P3 F8 1.548(15) 6_556
P3 F8 1.548(15) 3
P3 F8 1.548(15) 2
P3 F8 1.548(15) 5_556
P3 F8 1.548(16) 4_556
P4 F9 1.57(3) 3_565
P4 F9 1.57(3) .
P4 F9 1.57(3) 2_665
P4 F10 1.57(5) 2_665
P4 F10 1.57(5) 3_565
P4 F10 1.57(5) .
