#------------------------------------------------------------------------------
#$Date: 2019-11-24 03:27:53 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236489 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/40/1554046.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_1554046
loop_
_publ_author_name
'Pitrat, Delphine'
'Daugey, Nicolas'
'Jean, Marion'
'Vanthuyne, Nicolas'
'Wien, Frank'
'Ducasse, Laurent'
'Calin, Nathalie'
'Buffeteau, Thierry'
'Brotin, Thierry'
_publ_section_title
;
 Unusual Chiroptical Properties of the Cryptophane-222 Skeleton.
;
_journal_issue                   49
_journal_name_full               'The journal of physical chemistry. B'
_journal_page_first              12650
_journal_page_last               12659
_journal_paper_doi               10.1021/acs.jpcb.6b09771
_journal_volume                  120
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C48 H42 O6, C5 H5 N'
_chemical_formula_sum            'C53 H47 N O6'
_chemical_formula_weight         793.91
_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_Hall           'P 32 2"'
_space_group_name_H-M_alt        'P 32 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                120.000(5)
_cell_formula_units_Z            3
_cell_length_a                   11.549(5)
_cell_length_b                   11.549(5)
_cell_length_c                   27.874(5)
_cell_measurement_reflns_used    38375
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.8830
_cell_measurement_theta_min      4.2310
_cell_volume                     3220(2)
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_molecular_graphics    'SHELXLe  (Sheldrick, 2011)'
_computing_publication_material  'SHELXLe  (Sheldrick, 2011)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 0.9933
_diffrn_measured_fraction_theta_max 0.9920
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            76701
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         67.277
_diffrn_reflns_theta_min         4.421
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  0.866
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense colourless'
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.3084
_exptl_crystal_size_mid          0.2192
_exptl_crystal_size_min          0.1449
_platon_squeeze_details
;
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1  0.000  0.526  0.833        74        10 ' '
   2  0.474  0.474  0.500        73         9 ' '
   3  0.525  1.000  0.167        74        10 ' '
;
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1574 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.11(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3814
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0468
_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)+(0.0810P)²+1.3041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1258
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3763
_reflns_number_total             3814
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp6b09771_si_002.cif
_cod_data_source_block           cr222+
_cod_original_cell_volume        3220(3)
_cod_database_code               1554046
_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+2/3'
'-x+y, -x, z+1/3'
'y, x, -z'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
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
O1 O 0.3101(2) 0.11434(18) 0.63312(6) 0.0300(5) Uani 1 1 d . . . . .
C1 C 0.3785(3) 0.1947(3) 0.67359(9) 0.0237(5) Uani 1 1 d . . . . .
H1A H 0.453(3) 0.183(3) 0.6854(11) 0.028 Uiso 1 1 d . U . . .
H1B H 0.306(3) 0.157(3) 0.6978(11) 0.028 Uiso 1 1 d . U . . .
C2 C 0.4276(2) 0.3407(2) 0.66516(8) 0.0193(5) Uani 1 1 d . . . . .
H2A H 0.4661 0.3912 0.6943 0.023 Uiso 1 1 calc R U . . .
H2B H 0.4955 0.3752 0.6403 0.023 Uiso 1 1 calc R U . . .
O2 O 0.31558(17) 0.35239(18) 0.65069(6) 0.0232(4) Uani 1 1 d . . . . .
C3 C 0.3432(3) 0.4701(3) 0.62947(9) 0.0234(5) Uani 1 1 d . . . . .
C4 C 0.4620(3) 0.5894(3) 0.63459(10) 0.0304(6) Uani 1 1 d . . . . .
H4 H 0.5306 0.5944 0.6536 0.036 Uiso 1 1 calc R U . . .
C5 C 0.4769(4) 0.7015(3) 0.61088(10) 0.0396(8) Uani 1 1 d . . . . .
H5 H 0.5565 0.7819 0.6147 0.048 Uiso 1 1 calc R U . . .
C6 C 0.3785(4) 0.6992(3) 0.58168(9) 0.0377(8) Uani 1 1 d . . . . .
C7 C 0.2576(3) 0.5783(3) 0.57707(9) 0.0321(7) Uani 1 1 d . . . . .
C8 C 0.2407(3) 0.4655(3) 0.60172(9) 0.0270(6) Uani 1 1 d . . . . .
H8 H 0.1595 0.3859 0.5995 0.032 Uiso 1 1 calc R U . . .
C9 C 0.1425(4) 0.5604(4) 0.54549(10) 0.0425(9) Uani 1 1 d . . . . .
H9A H 0.0588 0.5013 0.5616 0.051 Uiso 1 1 calc R U . . .
H9B H 0.1478 0.6464 0.5414 0.051 Uiso 1 1 calc R U . . .
C10 C 0.1418(3) 0.5032(4) 0.49632(9) 0.0345(7) Uani 1 1 d . . . . .
C11 C 0.0796(3) 0.3647(4) 0.49191(10) 0.0363(7) Uani 1 1 d . . . . .
H11 H 0.0408 0.3123 0.5190 0.044 Uiso 1 1 calc R U . . .
C12 C 0.0731(3) 0.3021(3) 0.44898(9) 0.0314(7) Uani 1 1 d . . . . .
H12 H 0.0314 0.2094 0.4472 0.038 Uiso 1 1 calc R U . . .
C13 C 0.1909(3) 0.5186(3) 0.41166(9) 0.0282(6) Uani 1 1 d . . . . .
H13 H 0.2267 0.5701 0.3842 0.034 Uiso 1 1 calc R U . . .
C14 C 0.1994(3) 0.5818(3) 0.45549(10) 0.0334(7) Uani 1 1 d . . . . .
C15 C 0.2736(4) 0.7334(4) 0.45617(10) 0.0421(9) Uani 1 1 d . . . . .
H15A H 0.2594 0.7655 0.4259 0.050 Uiso 1 1 calc R U . . .
H15B H 0.2368 0.7633 0.4814 0.050 Uiso 1 1 calc R U . . .
C16 C 0.4222(4) 0.7939(3) 0.46434(9) 0.0370(8) Uani 1 1 d . . . . .
C17 C 0.5040(4) 0.8062(3) 0.42534(10) 0.0369(7) Uani 1 1 d . . . . .
H17 H 0.4645 0.7768 0.3954 0.044 Uiso 1 1 calc R U . . .
C18 C 0.6401(4) 0.8599(3) 0.42919(10) 0.0380(8) Uani 1 1 d . . . . .
H18 H 0.6912 0.8643 0.4027 0.046 Uiso 1 1 calc R U . . .
C19 C 0.6990(4) 0.9071(3) 0.47343(11) 0.0434(9) Uani 1 1 d D . . . .
O3A O 0.8577(5) 0.9785(6) 0.46989(17) 0.0279(12) Uani 0.5 1 d D U P A -2
C20 C 0.9275(5) 1.0076(5) 0.51545(18) 0.0267(11) Uani 0.5 1 d . . P A -1
H20A H 0.9287 1.0754 0.5363 0.032 Uiso 0.5 1 calc R U P A -1
H20B H 1.0104 1.0449 0.4975 0.032 Uiso 0.5 1 calc R U P A -1
C21 C 0.8994(5) 0.8836(5) 0.54248(18) 0.0233(10) Uani 0.5 1 d D . P A -1
H21A H 0.946(6) 0.903(6) 0.5729(12) 0.028 Uiso 0.5 1 d D U P B -1
H21B H 0.8043(19) 0.824(5) 0.547(2) 0.028 Uiso 0.5 1 d D U P C -1
C22 C 0.6229(4) 0.8982(3) 0.51249(11) 0.0462(10) Uani 1 1 d . . . . .
H22 H 0.6644 0.9312 0.5419 0.055 Uiso 1 1 calc R U . . .
C23 C 0.4848(4) 0.8406(3) 0.50901(10) 0.0427(9) Uani 1 1 d . . . . .
C24 C 0.4083(5) 0.8258(4) 0.55483(10) 0.0496(10) Uani 1 1 d . . . . .
H24A H 0.3250 0.8230 0.5472 0.060 Uiso 1 1 calc R U . . .
H24B H 0.4604 0.9028 0.5752 0.060 Uiso 1 1 calc R U . . .
C25 C 0.1300(3) 0.3804(3) 0.40844(9) 0.0272(6) Uani 1 1 d . . . . .
O3B O 0.8176(5) 0.9514(5) 0.48610(18) 0.0270(11) Uani 0.5 1 d D U P A -1
C1E C 0.9015(5) 1.0485(5) 0.6290(2) 0.075(2) Uani 0.5 1 d G U P D -1
H1E H 0.9421 1.1077 0.6036 0.090 Uiso 0.5 1 calc R U P D -1
C1B C 0.9660(4) 0.9878(5) 0.65064(18) 0.0530(19) Uani 0.5 1 d G U P D -1
H1BA H 1.0497 1.0064 0.6398 0.064 Uiso 0.5 1 calc R U P D -1
C1C C 0.9052(5) 0.8994(5) 0.68848(17) 0.0566(19) Uani 0.5 1 d G U P D -1
H1C H 0.9484 0.8588 0.7030 0.068 Uiso 0.5 1 calc R U P D -1
C1D C 0.7801(5) 0.8716(5) 0.70465(17) 0.0454(16) Uani 0.5 1 d G U P D -1
H1D H 0.7394 0.8124 0.7300 0.054 Uiso 0.5 1 calc R U P D -1
C1A C 0.7156(4) 0.9322(6) 0.6830(2) 0.063(3) Uani 0.5 1 d G U P D -1
H1AA H 0.6318 0.9136 0.6938 0.076 Uiso 0.5 1 calc R U P D -1
N1F N 0.7763(5) 1.0207(6) 0.6451(3) 0.053(2) Uani 0.5 1 d G U P D -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C25 O1 C1 118.9(2) 4_556
O1 C1 C2 112.5(2) .
O2 C2 C1 107.4(2) .
C3 O2 C2 116.47(19) .
O2 C3 C4 124.7(2) .
O2 C3 C8 115.5(2) .
C4 C3 C8 119.8(3) .
C3 C4 C5 118.7(3) .
C4 C5 C6 123.0(3) .
C5 C6 C7 118.1(3) .
C5 C6 C24 118.7(3) .
C7 C6 C24 123.1(3) .
C8 C7 C6 119.3(3) .
C8 C7 C9 116.9(3) .
C6 C7 C9 123.8(3) .
C3 C8 C7 121.1(3) .
C10 C9 C7 113.3(2) .
C11 C10 C14 118.6(3) .
C11 C10 C9 117.8(3) .
C14 C10 C9 123.6(3) .
C12 C11 C10 122.6(3) .
C11 C12 C25 118.7(3) .
C25 C13 C14 121.3(3) .
C10 C14 C13 118.9(3) .
C10 C14 C15 123.4(3) .
C13 C14 C15 117.7(3) .
C16 C15 C14 113.1(2) .
C17 C16 C23 117.2(4) .
C17 C16 C15 118.8(3) .
C23 C16 C15 123.9(3) .
C18 C17 C16 123.1(3) .
C17 C18 C19 118.2(3) .
O3B C19 C22 109.7(4) .
O3B C19 C18 129.5(4) .
C22 C19 C18 120.6(4) .
C22 C19 O3A 128.1(3) .
C18 C19 O3A 111.1(3) .
O3B C20 C21 98.1(5) .
C19 C22 C23 121.3(3) .
C22 C23 C16 119.5(3) .
C22 C23 C24 117.4(3) .
C16 C23 C24 123.1(4) .
C23 C24 C6 111.3(2) .
O1 C25 C13 125.1(2) 4_556
O1 C25 C12 114.9(3) 4_556
C13 C25 C12 119.9(3) .
C19 O3B C20 158.2(5) .
C1B C1E N1F 120.0 .
C1C C1B C1E 120.0 .
C1B C1C C1D 120.0 .
C1A C1D C1C 120.0 .
N1F C1A C1D 120.0 .
C1A N1F C1E 120.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C25 1.374(3) 4_556
O1 C1 1.423(3) .
C1 C2 1.505(3) .
C2 O2 1.424(3) .
O2 C3 1.366(3) .
C3 C4 1.383(4) .
C3 C8 1.393(4) .
C4 C5 1.385(4) .
C5 C6 1.388(5) .
C6 C7 1.402(5) .
C6 C24 1.520(4) .
C7 C8 1.398(4) .
C7 C9 1.521(4) .
C9 C10 1.520(4) .
C10 C11 1.393(5) .
C10 C14 1.399(4) .
C11 C12 1.381(4) .
C12 C25 1.390(4) .
C13 C25 1.388(4) .
C13 C14 1.402(4) .
C14 C15 1.516(5) .
C15 C16 1.512(5) .
C16 C17 1.400(5) .
C16 C23 1.405(4) .
C17 C18 1.375(5) .
C18 C19 1.382(4) .
C19 O3B 1.250(6) .
C19 C22 1.370(5) .
C19 O3A 1.594(6) .
C20 O3B 1.370(7) .
C20 C21 1.503(7) .
C22 C23 1.391(6) .
C23 C24 1.513(5) .
C25 O1 1.374(3) 4_556
C1E C1B 1.3900 .
C1E N1F 1.3900 .
C1B C1C 1.3900 .
C1C C1D 1.3900 .
C1D C1A 1.3900 .
C1A N1F 1.3900 .
