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_1564256
_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 H46 O10, C5 H10 O3'
_chemical_formula_sum            'C48 H56 O13'
_chemical_formula_weight         840.92
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-04
_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                 98.7260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.2498(2)
_cell_length_b                   11.99340(10)
_cell_length_c                   17.88350(10)
_cell_measurement_reflns_used    31207
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      74.2060
_cell_measurement_theta_min      2.4810
_cell_volume                     4504.99(6)
_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      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_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    -67.00  27.00   0.50    0.71    --  -46.12  71.00  12.00  188
  2  \w    -61.00  29.00   0.50    0.71    --  -46.12  19.00   0.00  180
  3  \w    -26.00  67.00   0.50    0.71    --   46.12 -71.00-118.00  186
  4  \w     29.00 123.00   0.50    2.85    --  101.75 -71.00-118.00  188
  5  \w     87.00 174.00   0.50    2.85    --  101.75  45.00-180.00  174
  6  \w     81.00 175.00   0.50    2.85    --  101.75  71.00  12.00  188
  7  \w     78.00 175.00   0.50    2.85    --  101.75  77.00  90.00  194
  8  \w     29.00 117.00   0.50    2.85    --  101.75-125.00  30.00  176
  9  \w     29.00 116.00   0.50    2.85    --  101.75 -45.00-120.00  174
 10  \w     25.00 118.00   0.50    0.71    --   46.12  71.00  12.00  186
 11  \w     29.00 116.00   0.50    2.85    --  101.75 -45.00 -30.00  174
 12  \w     29.00 109.00   0.50    2.85    --  101.75 -94.00  90.00  160
 13  \w     20.00  95.00   0.50    0.71    --   46.12-125.00-150.00  150
 14  \w     23.00 118.00   0.50    0.71    --   46.12  77.00  90.00  190
 15  \w   -118.00 -25.00   0.50    0.71    --  -46.12 -71.00-118.00  186
 16  \w   -118.00 -73.00   0.50    0.71    --  -46.12-125.00-150.00   90
 17  \w   -118.00 -73.00   0.50    0.71    --  -46.12-125.00 -30.00   90
 18  \w   -118.00 -73.00   0.50    0.71    --  -46.12-125.00  60.00   90
 19  \w   -118.00 -22.00   0.50    0.71    --  -46.12 -77.00 -30.00  192
 20  \w   -115.00 -25.00   0.50    2.85    -- -100.00  30.00 -60.00  180
 21  \w   -117.00 -27.00   0.50    2.85    -- -100.00  61.00 120.00  180
 22  \w   -121.00 -27.00   0.50    2.85    -- -100.00  71.00  12.00  188
 23  \w   -173.00 -79.00   0.50    2.85    -- -100.00 -71.00-118.00  188
 24  \w   -173.00 -82.00   0.50    2.85    -- -100.00 -61.00 -30.00  182
 25  \w   -176.00 -82.00   0.50    2.85    -- -100.00 -15.00 120.00  188
 26  \w   -175.00 -84.00   0.50    2.85    -- -100.00 -30.00  90.00  182
 27  \w   -172.00 -85.00   0.50    2.85    -- -100.00 -45.00 -60.00  174
 28  \w   -176.00 -82.00   0.50    2.85    -- -100.00 -15.00-150.00  188
 29  \w   -173.00 -82.00   0.50    2.85    -- -100.00 -61.00 -60.00  182
 30  \w   -172.00 -85.00   0.50    2.85    -- -100.00 -45.00-180.00  174
;
_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      0.0056570000
_diffrn_orient_matrix_UB_12      -0.0615722000
_diffrn_orient_matrix_UB_13      -0.0742868000
_diffrn_orient_matrix_UB_21      -0.0478631000
_diffrn_orient_matrix_UB_22      0.0820628000
_diffrn_orient_matrix_UB_23      -0.0437435000
_diffrn_orient_matrix_UB_31      0.0552801000
_diffrn_orient_matrix_UB_32      0.0773088000
_diffrn_orient_matrix_UB_33      -0.0127704000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            42011
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.584
_diffrn_reflns_theta_min         2.500
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95171
_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    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 3786 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         8931
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0755P)^2^+1.2004P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1146
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                8567
_reflns_number_total             8931
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02560k2.cif
_cod_data_source_block           dijydroxy_p5
_cod_database_code               1564256
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.867
_reflns_odcompleteness_completeness 100.00
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C43(H43)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C47(H47A,H47B), C48(H48A,H48B), C33(H33A,H33B), C18(H18A,H18B),
 C45(H45A,H45B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C35(H35), C26(H26), C14(H14), C3(H3), C38(H38), C24(H24),
 C29(H29), C21(H21)
2.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C41(H41A,H41B,
 H41C), C31(H31A,H31B,H31C), C8(H8A,H8B,H8C), C40(H40A,H40B,H40C), C9(H9A,H9B,
 H9C), C46(H46A,H46B,H46C), C42(H42A,H42B,H42C)
2.e Idealised tetrahedral OH refined as rotating group:
 O9(H9), O8(H8), O1(H1)
;
_shelx_res_checksum              97426
_shelx_hkl_checksum              85578
_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 1.758
_oxdiff_exptl_absorpt_empirical_full_min 0.514