Stereochemical Inversion of Rim-Differentiated Pillar[5]arene Molecular Swings
Du, Ke; Demay-Drouhard, Paul; Samanta, Kushal; Li, Shunshun; Thikekar, Tushar Ulhas; Wang, Haiying; Guo, Minjie; van Lagen, Barend; Zuilhof, Han; Sue, Andrew C.-H.; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.0c01464

data_4038709
_publ_section_title
;
 Stereochemical Inversion of Rim-Differentiated Pillar[5]arene Molecular
 Swings
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01464
_journal_year                    2020
_chemical_formula_moiety         'C55 H70 O10, C6 H14'
_chemical_formula_sum            'C61 H84 O10'
_chemical_formula_weight         977.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.84906(18)
_cell_length_b                   14.08840(11)
_cell_length_c                   38.1251(3)
_cell_measurement_reflns_used    29588
_cell_measurement_temperature    160.00(10)
_cell_measurement_theta_max      74.5800
_cell_measurement_theta_min      3.1520
_cell_volume                     11198.48(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     31.00 119.00   0.50    1.13    --   45.87  52.00-114.00  176
  2  \w     92.00 170.00   0.50    4.54    --  101.75  30.00  30.00  156
  3  \w     41.00 107.00   0.50    4.54    --  101.75-125.00 120.00  132
  4  \w     20.00  95.00   0.50    1.13    --   45.87-125.00 120.00  150
  5  \w    -61.00  27.00   0.50    1.13    --  -45.87  52.00-114.00  176
  6  \w   -115.00 -27.00   0.50    4.54    -- -100.00  52.00-114.00  176
  7  \w   -115.00 -85.00   0.50    4.54    -- -100.00  30.00   0.00   60
  8  \w   -123.00 -27.00   0.50    4.54    -- -100.00  75.00  22.00  192
  9  \w   -110.00 -27.00   0.50    4.54    -- -100.00 102.00 112.00  166
 10  \w   -119.00 -73.00   0.50    1.13    --  -45.87-125.00-120.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0462510000
_diffrn_orient_matrix_UB_12      0.0681103000
_diffrn_orient_matrix_UB_13      -0.0189405000
_diffrn_orient_matrix_UB_21      0.0059067000
_diffrn_orient_matrix_UB_22      -0.0597067000
_diffrn_orient_matrix_UB_23      -0.0336728000
_diffrn_orient_matrix_UB_31      -0.0573623000
_diffrn_orient_matrix_UB_32      -0.0611839000
_diffrn_orient_matrix_UB_33      0.0118415000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            56051
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.709
_diffrn_reflns_theta_min         2.318
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_description       plate
_exptl_crystal_F_000             4240
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     652
_refine_ls_number_reflns         11038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0406
_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/[\s^2^(Fo^2^)+(0.0576P)^2^+3.0388P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1165
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9215
_reflns_number_total             11038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01464_si_002.cif
_cod_data_source_block           rd-p5-propyl
_cod_database_code               4038709
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C28(H28A,H28B), C42(H42A,H42B), C3(H3A,H3B), C61(H61A,H61B),
 C15(H15A,H15B), C2(H2A,H2B), C49(H49A,H49B), C14(H14A,H14B), C9(H9A,H9B),
 C6(H6A,H6B), C12(H12A,H12B), C8(H8A,H8B), C5(H5A,H5B), C58(H58A,H58B),
 C57(H57A,H57B), C11(H11A,H11B), C56(H56A,H56B), C59(H59A,H59B)
2.b Aromatic/amide H refined with riding coordinates:
 C34(H34), C24(H24), C45(H45), C31(H31), C48(H48), C27(H27), C38(H38),
 C41(H41), C17(H17), C20(H20)
2.c Idealised Me refined as rotating group:
 C50(H50A,H50B,H50C), C51(H51A,H51B,H51C), C13(H13A,H13B,H13C), C54(H54A,H54B,
 H54C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C1(H1A,H1B,H1C), C60(H60A,
 H60B,H60C), C7(H7A,H7B,H7C), C4(H4A,H4B,H4C), C10(H10A,H10B,H10C), C55(H55A,
 H55B,H55C)
;
_shelx_res_checksum              62759
_shelx_hkl_checksum              80823
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.391
_oxdiff_exptl_absorpt_empirical_full_min 0.778