Spontaneous and induced chiral symmetry breaking of stereolabile pillar[5]arene derivatives upon crystallisation
Wang, Haiying; Yang, Weiwei; Baldridge, Kim K.; Zhan, Cai-Hong; Thikekar, Tushar Ulhas; Sue, Andrew C.-H.; Chemical Science  (2021) –; doi:10.1039/D1SC02560K

data_1564255
_publ_section_title
;
 Spontaneous and induced chiral symmetry breaking of stereolabile
 pillar[5]arene derivatives upon crystallisation
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02560K
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C43 H44 O10, C5 H10 O3'
_chemical_formula_sum            'C48 H54 O13'
_chemical_formula_weight         838.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-27 deposited with the CCDC.	2021-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.805(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.1145(4)
_cell_length_b                   12.0659(3)
_cell_length_c                   17.7473(3)
_cell_measurement_reflns_used    10620
_cell_measurement_temperature    159.99(10)
_cell_measurement_theta_max      71.4400
_cell_measurement_theta_min      2.5230
_cell_volume                     4468.11(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_temperature      159.99(10)
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.944
_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   -121.00 -31.00   0.50    1.00    --  -46.12 -22.00 -90.00  180
  2  \w    -77.00 -29.00   0.50    4.00    -- -100.00  61.00-180.00   96
  3  \w    -93.00 -51.00   0.50    1.00    --  -46.12 125.00 -90.00   84
  4  \w    -94.00 -20.00   0.50    1.00    --  -46.12 125.00  30.00  148
  5  \w    -56.00 -27.00   0.50    4.00    -- -100.00 125.00 150.00   58
  6  \w    -40.00 -15.00   0.50    1.00    --  -46.12  22.00  75.00   50
  7  \w    -29.00  61.00   0.50    1.00    --   46.12 -22.00 -90.00  180
  8  \w     32.00  88.00   0.50    1.00    --   46.12  57.00-180.00  112
  9  \w     77.00 103.00   0.50    1.00    --   46.12  77.00-150.00   52
 10  \w     44.00  74.00   0.50    1.00    --   46.12  77.00-150.00   60
 11  \w     23.00 117.00   0.50    1.00    --   46.12  77.00-180.00  188
 12  \w     32.00 123.00   0.50    4.00    --  107.75 -22.00 -90.00  182
 13  \w     54.00 122.00   0.50    4.00    --  107.75 -45.00  60.00  136
 14  \w     95.00 150.00   0.50    4.00    --  107.75  22.00  75.00  110
 15  \w     45.00  80.00   0.50    1.00    --   46.12  77.00  90.00   70
 16  \w     32.00 121.00   0.50    1.00    --   46.12  22.00  75.00  178
 17  \w     31.00 119.00   0.50    1.00    --   46.12  37.00 120.00  176
 18  \w     30.00  75.00   0.50    1.00    --   46.12  57.00 150.00   90
 19  \w     35.00 108.00   0.50    4.00    --  107.75 -94.00   0.00  146
 20  \w     35.00  66.00   0.50    4.00    --  107.75 -94.00-120.00   62
 21  \w   -115.00 -24.00   0.50    4.00    -- -100.00  22.00  75.00  182
 22  \w   -101.00 -76.00   0.50    4.00    -- -100.00 -77.00 150.00   50
 23  \w   -103.00 -78.00   0.50    4.00    -- -100.00 -72.00 156.65   50
 24  \w   -108.00 -77.00   0.50    4.00    -- -100.00 -77.00 120.00   62
 25  \w   -107.00 -81.00   0.50    4.00    -- -100.00 -64.00 139.13   52
 26  \w   -111.00 -79.00   0.50    4.00    -- -100.00 -70.00 124.53   64
 27  \w   -109.00 -83.00   0.50    4.00    -- -100.00 -61.00 155.76   52
 28  \w   -109.00 -83.00   0.50    4.00    -- -100.00 -61.00 150.00   52
 29  \w   -113.00 -84.00   0.50    4.00    -- -100.00 -55.00 106.87   58
 30  \w   -107.00 -81.00   0.50    4.00    -- -100.00 -69.00 133.01   52
 31  \w   -119.00 -82.00   0.50    4.00    -- -100.00 -61.00 172.11   74
 32  \w   -162.00-136.00   0.50    4.00    -- -100.00 -77.00 150.00   52
 33  \w   -160.00 -86.00   0.50    4.00    -- -100.00 -47.00 121.54  148
 34  \w   -172.00-108.00   0.50    4.00    -- -100.00 -72.00 156.65  128
 35  \w   -173.00-116.00   0.50    4.00    -- -100.00 -77.00 120.00  114
 36  \w   -176.00 -85.00   0.50    4.00    -- -100.00 -22.00 -90.00  182
 37  \w   -108.00 -82.00   0.50    4.00    -- -100.00 -61.00-150.00   52
 38  \w   -101.00 -76.00   0.50    4.00    -- -100.00 -77.00-120.00   50
 39  \w   -106.00 -79.00   0.50    4.00    -- -100.00 -71.00-168.93   54
 40  \w   -110.00 -84.00   0.50    4.00    -- -100.00 -58.00-158.09   52
 41  \w   -101.00 -76.00   0.50    4.00    -- -100.00 -77.00-150.00   50
 42  \w   -105.00 -80.00   0.50    4.00    -- -100.00 -71.00-177.90   50
 43  \w   -102.00 -77.00   0.50    4.00    -- -100.00 -74.00-114.38   50
 44  \w   -107.00 -82.00   0.50    4.00    -- -100.00 -62.00-116.09   50
 45  \w   -105.00 -79.00   0.50    4.00    -- -100.00 -70.00-177.91   52
 46  \w   -104.00 -78.00   0.50    4.00    -- -100.00 -77.00-180.00   52
 47  \w   -108.00 -82.00   0.50    4.00    -- -100.00 -61.00-180.00   52
 48  \w   -110.00 -84.00   0.50    4.00    -- -100.00 -61.00-120.00   52
 49  \w   -107.00 -81.00   0.50    4.00    -- -100.00 -65.00-163.01   52
 50  \w   -105.00 -79.00   0.50    4.00    -- -100.00 -73.00-118.96   52
 51  \w   -129.00 -95.00   0.50    4.00    -- -100.00 -46.00-155.37   68
 52  \w   -164.00-139.00   0.50    4.00    -- -100.00 -77.00-150.00   50
 53  \w   -168.00-142.00   0.50    4.00    -- -100.00 -77.00-120.00   52
 54  \w   -171.00-134.00   0.50    4.00    -- -100.00 -46.00-155.37   74
 55  \w   -173.00 -84.00   0.50    4.00    -- -100.00 -58.00-160.75  178
 56  \w   -115.00 -82.00   0.50    4.00    -- -100.00  61.00-180.00   66
 57  \w   -172.00 -86.00   0.50    4.00    -- -100.00 -45.00-127.60  172
 58  \w   -117.00 -68.00   0.50    4.00    -- -100.00 125.00 150.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            41754
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.460
_diffrn_reflns_theta_min         2.519
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81507
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             1784
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 2476 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         8631
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0509
_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/[\s^2^(Fo^2^)+(0.0743P)^2^+1.2806P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1375
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                6646
_reflns_number_total             8631
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02560k2.cif
_cod_data_source_block           028463_tushar_b
_cod_database_code               1564255
_shelx_shelxl_version_number     2018/3
_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. Restrained distances
 H11-O11
 0.9 with sigma of 0.02
 H11-O7_$1
 2.1 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C25(H25A,H25B), C34(H34A,H34B), C43(H43A,H43B), C7(H7A,H7B),
 C47(H47A,H47B)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C22(H22), C19(H19), C28(H28), C37(H37), C13(H13), C31(H31), C5(H5),
 C2(H2), C40(H40)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C24(H24A,H24B,H24C), C35(H35A,H35B,H35C), C26(H26A,H26B,
 H26C), C17(H17A,H17B,H17C), C42(H42A,H42B,H42C), C15(H15A,H15B,H15C), C33(H33A,
 H33B,H33C), C48(H48A,H48B,H48C), C44(H44A,H44B,H44C)
;
_shelx_res_checksum              47553
_shelx_hkl_checksum              54498
_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
;