Inherently chiral calixarenes by a catalytic enantioselective desymmetrizing cross-dehydrogenative coupling.
Zhang, Xin; Tong, Shuo; Zhu, Jieping; Wang, Mei-Xiang; Chemical science 14 (2023) 827–832; doi:10.1039/d2sc06234h

data_1568046
_publ_section_title
;
 Inherently chiral calixarenes by a catalytic enantioselective
 desymmetrizing cross-dehydrogenative coupling.
;
_journal_issue                   4
_journal_name_full               'Chemical science'
_journal_page_first              827
_journal_page_last               832
_journal_paper_doi               10.1039/d2sc06234h
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C51 H56 O5'
_chemical_formula_sum            'C51 H56 O5'
_chemical_formula_weight         748.95
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2dd6hj
_audit_creation_date             2022-10-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-10-29 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                80.2660(10)
_cell_angle_beta                 79.8290(10)
_cell_angle_gamma                76.8500(10)
_cell_formula_units_Z            2
_cell_length_a                   9.35900(10)
_cell_length_b                   12.70520(10)
_cell_length_c                   18.77490(10)
_cell_measurement_reflns_used    50133
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      77.3360
_cell_measurement_theta_min      2.3780
_cell_volume                     2120.34(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.949
_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   -106.00 -32.00   0.50    0.05    -- -104.00  94.00  -0.00  148
  2  \w   -126.00 -57.00   0.50    0.05    -- -104.00 144.00 -78.63  138
  3  \w    -64.00 -35.00   0.50    0.05    -- -104.00  57.00 120.00   58
  4  \w    -78.00  24.00   0.50    0.05    --  -48.14  94.00  -0.00  204
  5  \w    -21.00  17.00   0.50    0.05    --   12.00 101.00-155.62   76
  6  \w    -19.00  28.00   0.50    0.05    --   12.00  96.00 -76.46   94
  7  \w    -15.00  27.00   0.50    0.05    --   16.00  97.00  77.11   84
  8  \w      1.00  28.00   0.50    0.05    --   32.00  96.00 169.40   54
  9  \w     11.00  40.00   0.50    0.05    --   40.00  92.00 -11.34   58
 10  \w     16.00  42.00   0.50    0.05    --   44.00  90.00 -82.10   52
 11  \w     27.00 120.00   0.50    0.05    --   48.14  77.00-150.00  186
 12  \w     30.00 124.00   0.50    0.05    --   52.00  77.00-134.30  188
 13  \w     34.00 128.00   0.50    0.05    --   56.00  77.00 -16.61  188
 14  \w    107.00 133.00   0.50    0.05    --   64.00  77.00 -12.50   52
 15  \w     42.00  68.00   0.50    0.05    --   64.00  77.00 -12.50   52
 16  \w     30.00 124.00   0.50    0.05    --   52.00  77.00  44.75  188
 17  \w     27.00 120.00   0.50    0.05    --   48.14  77.00  90.00  186
 18  \w     30.00 124.00   0.50    0.05    --   52.00  77.00  97.44  188
 19  \w     35.00 128.00   0.50    0.05    --   56.00  76.00 135.97  186
 20  \w     43.00  69.00   0.50    0.05    --   64.00  76.00  98.55   52
 21  \w     36.00 128.00   0.50    0.05    --   56.00  73.00-113.28  184
 22  \w     44.00  70.00   0.50    0.05    --   64.00  72.00 -97.82   52
 23  \w     47.00  73.00   0.50    0.05    --   68.00  76.00-155.31   52
 24  \w     89.00 116.00   0.50    0.05    --   68.00  76.00-155.31   54
 25  \w     51.00  81.00   0.50    0.05    --   68.00  68.00-116.35   60
 26  \w     41.00  67.00   0.50    0.05    --   60.00  71.00 -53.90   52
 27  \w     78.00 106.00   0.50    0.05    --   60.00  71.00 -53.90   56
 28  \w     88.00 178.00   0.50    0.05    --  106.93  94.00  -0.00  180
 29  \w     42.00  68.00   0.50    0.05    --  106.93 -57.00 -90.00   52
 30  \w     43.00 107.00   0.50    0.05    --  106.93 -77.00-120.00  128
 31  \w    -24.00  45.00   0.50    0.05    --   48.14 -38.00 -60.00  138
 32  \w    -23.00  78.00   0.50    0.05    --   48.14 -94.00-111.00  202
 33  \w     62.00 109.00   0.50    0.05    --  106.93-125.00-180.00   94
 34  \w     81.00 109.00   0.50    0.05    --  106.93-125.00  30.00   56
 35  \w     38.00  75.00   0.50    0.05    --  106.93-125.00  30.00   74
 36  \w     35.00 109.00   0.50    0.05    --  106.93-125.00  60.00  148
 37  \w     36.00 100.00   0.50    0.05    --  106.93 -99.00  60.00  128
 38  \w     36.00  68.00   0.50    0.05    --  106.93 -99.00  90.00   64
 39  \w     39.00 104.00   0.50    0.05    --  106.93 -99.00 120.00  130
 40  \w     77.00 103.00   0.50    0.05    --  106.93 -99.00  90.00   52
 41  \w     35.00 106.00   0.50    0.05    --  106.93 -94.00-111.00  142
 42  \w     40.00 103.00   0.50    0.05    --  106.93 -99.00-120.00  126
 43  \w     36.00 106.00   0.50    0.05    --  106.93 -99.00-180.00  140
 44  \w     41.00  75.00   0.50    0.05    --  106.93 -99.00-150.00   68
 45  \w   -120.00 -81.00   0.50    0.05    -- -104.00 -80.00  16.20   78
 46  \w    -80.00 -54.00   0.50    0.05    --  -76.00 -77.00  78.76   52
 47  \w   -123.00 -74.00   0.50    0.05    --  -96.00 -77.00 121.14   98
 48  \w   -165.00-139.00   0.50    0.05    --  -96.00 -77.00 121.14   52
 49  \w   -172.00-133.00   0.50    0.05    -- -104.00 -80.00  16.20   78
 50  \w    -79.00 -47.00   0.50    0.05    --  -68.00 -76.00  36.93   64
 51  \w   -120.00 -26.00   0.50    0.05    --  -48.14 -77.00 120.00  188
 52  \w   -120.00 -26.00   0.50    0.05    --  -48.14 -77.00 150.00  188
 53  \w   -109.00 -82.00   0.50    0.05    -- -104.00 -77.00 150.00   54
 54  \w   -173.00-113.00   0.50    0.05    -- -104.00 -77.00 150.00  120
 55  \w    -80.00 -55.00   0.50    0.05    --  -76.00 -76.00 119.44   50
 56  \w    -77.00 -51.00   0.50    0.05    --  -72.00 -76.00 147.40   52
 57  \w    -98.00 -71.00   0.50    0.05    --  -92.00 -76.00  51.54   54
 58  \w    -94.00 -67.00   0.50    0.05    --  -88.00 -75.00  99.37   54
 59  \w   -158.00-129.00   0.50    0.05    --  -88.00 -75.00  99.37   58
 60  \w   -163.00-127.00   0.50    0.05    --  -92.00 -76.00  51.54   72
 61  \w   -160.00-124.00   0.50    0.05    --  -88.00 -75.00  21.25   72
 62  \w    -77.00 -51.00   0.50    0.05    --  -72.00 -75.00 122.69   52
 63  \w    -96.00 -67.00   0.50    0.05    --  -88.00 -75.00  21.25   58
 64  \w    -92.00 -53.00   0.50    0.05    --  -72.00 -75.00 -62.70   78
 65  \w    -85.00 -59.00   0.50    0.05    --  -80.00 -75.00 -73.96   52
 66  \w   -101.00 -75.00   0.50    0.05    --  -96.00 -76.00-128.91   52
 67  \w   -161.00-107.00   0.50    0.05    --  -96.00 -76.00-128.91  108
 68  \w   -158.00-120.00   0.50    0.05    --  -88.00 -74.00-100.98   76
 69  \w   -157.00 -67.00   0.50    0.05    --  -88.00 -74.00 -92.85  180
 70  \w   -113.00 -69.00   0.50    0.05    --  -88.00 -74.00-100.98   88
 71  \w    -99.00 -73.00   0.50    0.05    --  -92.00 -74.00 -15.97   52
 72  \w    -64.00 -39.00   0.50    0.05    --  -60.00 -74.00  42.61   50
 73  \w    -66.00 -40.00   0.50    0.05    --  -60.00 -74.00 142.65   52
 74  \w   -104.00 -72.00   0.50    0.05    --  -92.00 -74.00 175.43   64
 75  \w   -164.00-123.00   0.50    0.05    --  -92.00 -74.00 175.43   82
 76  \w   -127.00-100.00   0.50    0.05    --  -60.00 -74.00  42.61   54
 77  \w   -164.00-119.00   0.50    0.05    --  -92.00 -74.00 -15.97   90
 78  \w    -98.00 -67.00   0.50    0.05    --  -88.00 -74.00-125.49   62
 79  \w    -82.00 -56.00   0.50    0.05    --  -76.00 -73.00-162.21   52
 80  \w    -87.00 -61.00   0.50    0.05    --  -80.00 -73.00 -33.39   52
 81  \w    -89.00 -60.00   0.50    0.05    --  -80.00 -73.00 -17.96   58
 82  \w    -74.00 -48.00   0.50    0.05    --  -68.00 -72.00  -8.37   52
 83  \w    -88.00 -62.00   0.50    0.05    --  -80.00 -71.00  -2.35   52
 84  \w    -80.00 -54.00   0.50    0.05    --  -72.00 -69.00   6.46   52
 85  \w   -173.00 -85.00   0.50    0.05    -- -104.00 -70.00  -1.10  176
 86  \w   -158.00 -69.00   0.50    0.05    --  -88.00 -73.00  86.39  178
 87  \w    -86.00 -60.00   0.50    0.05    --  -80.00 -73.00 173.60   52
 88  \w   -101.00 -75.00   0.50    0.05    --  -92.00 -68.00 117.67   52
 89  \w    -89.00 -64.00   0.50    0.05    --  -84.00 -72.00 128.41   50
 90  \w    -92.00 -66.00   0.50    0.05    --  -84.00 -67.00  96.80   52
 91  \w   -157.00 -73.00   0.50    0.05    --  -92.00 -69.00  71.06  168
 92  \w   -162.00-126.00   0.50    0.05    --  -92.00 -68.00 117.67   72
 93  \w    -92.00 -66.00   0.50    0.05    --  -84.00 -68.00 -57.29   52
 94  \w    -80.00 -54.00   0.50    0.05    --  -72.00 -68.00-123.71   52
 95  \w    -92.00 -66.00   0.50    0.05    --  -84.00 -67.00-176.17   52
 96  \w   -148.00 -74.00   0.50    0.05    --  -92.00 -67.00-157.97  148
 97  \w   -153.00-113.00   0.50    0.05    --  -84.00 -67.00-176.17   80
 98  \w   -167.00-126.00   0.50    0.05    --  -96.00 -65.00 -68.56   82
 99  \w    -93.00 -67.00   0.50    0.05    --  -84.00 -66.00  24.20   52
100  \w   -165.00 -87.00   0.50    0.05    -- -104.00 -65.00 138.98  156
101  \w   -156.00-122.00   0.50    0.05    --  -88.00 -65.00 169.93   68
102  \w   -106.00 -71.00   0.50    0.05    --  -88.00 -65.00 169.93   70
103  \w   -114.00 -74.00   0.50    0.05    --  -92.00 -67.00 148.84   80
104  \w    -97.00 -71.00   0.50    0.05    --  -88.00 -64.00  41.93   52
105  \w   -160.00-108.00   0.50    0.05    --  -88.00 -64.00  41.93  104
106  \w   -108.00 -79.00   0.50    0.05    --  -96.00 -65.00 -68.56   58
107  \w    -80.00 -55.00   0.50    0.05    --  -72.00 -65.00-119.71   50
108  \w   -157.00 -81.00   0.50    0.05    --  -96.00 -60.00 -58.36  152
109  \w   -159.00-122.00   0.50    0.05    --  -88.00 -62.00 -47.73   74
110  \w   -110.00 -78.00   0.50    0.05    --  -88.00 -62.00 -47.73   64
111  \w   -175.00 -84.00   0.50    0.05    -- -104.00 -94.00-111.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1060833000
_diffrn_orient_matrix_UB_12      0.0301753000
_diffrn_orient_matrix_UB_13      0.0437057000
_diffrn_orient_matrix_UB_21      0.1255836000
_diffrn_orient_matrix_UB_22      -0.0156007000
_diffrn_orient_matrix_UB_23      -0.0648500000
_diffrn_orient_matrix_UB_31      -0.0464109000
_diffrn_orient_matrix_UB_32      0.1209828000
_diffrn_orient_matrix_UB_33      -0.0310151000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            75676
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.791
_diffrn_reflns_theta_min         2.413
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.55a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_description       block
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     528
_refine_ls_number_reflns         8594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0620
_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^)+(0.0670P)^2^+1.6764P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.1663
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7637
_reflns_number_total             8594
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06234h2.cif
_cod_data_source_block           zx-cp-rac_auto
_cod_depositor_comments
'Adding full bibliography for 1568045--1568046.cif.'
_cod_database_code               1568046
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c h o'
_chemical_oxdiff_usercomment     'C H O'
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.893
_reflns_odcompleteness_completeness 99.89
_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. Others
 Fixed Sof: H01X(0.5) H01Y(0.5) C01J(0.5) H1(0.5) HD(0.5) C01K(0.5) H2(0.5)
 HE(0.5) HF(0.5) C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5) C8(0.5) H8A(0.5) H8B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C00P(H00B,H00C), C00V(H00D,H00E), C00Z(H00F,H00G), C010(H01A,H01B), C012(H01C,
 H01D), C015(H01E,H01F), C016(H01G,H01H), C019(H01I,H01J), C01A(H01K,H01L),
 C01B(H01M,H01N), C01D(H01R,H01S), C01E(H01T,H01U), C01F(H01V,H01W), C01G(H01X,
 H01Y), C01J(H1,HD), C8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00J(H00J), C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R),
 C00T(H00T), C00U(H00U), C00X(H00X), C00Y(H00Y), C011(H011), C013(H013),
 C014(H014), C017(H017), C018(H018)
3.c Idealised Me refined as rotating group:
 C01C(H01O,H01P,H01Q), C01H(H01Z,H,HA), C01I(H01,HB,HC), C01K(H2,HE,HF),
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              7885
_shelx_hkl_checksum              43237
_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 3.568
_oxdiff_exptl_absorpt_empirical_full_min 0.532