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_1568045
_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 H58 O5'
_chemical_formula_sum            'C51 H58 O5'
_chemical_formula_weight         750.97
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2dd6gh
_audit_creation_date             2022-10-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-10-29 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                93.1420(10)
_cell_angle_beta                 105.2290(10)
_cell_angle_gamma                97.6850(10)
_cell_formula_units_Z            2
_cell_length_a                   10.6821(2)
_cell_length_b                   12.08420(10)
_cell_length_c                   17.0570(2)
_cell_measurement_reflns_used    24002
_cell_measurement_temperature    100.2(5)
_cell_measurement_theta_max      66.3600
_cell_measurement_theta_min      4.2650
_cell_volume                     2096.06(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.2(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_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    -89.00  89.00   0.50    0.50    --    0.00  55.00  48.28  356
  2  \w    -41.00 137.00   0.50    0.50    --   48.00  54.00-156.35  356
  3  \w    -37.00 141.00   0.50    0.50    --   52.00  51.00  -6.33  356
  4  \w     -5.00 173.00   0.50    1.98    --   84.00  55.00 156.94  356
  5  \w    120.00 178.00   0.50    1.98    --   90.00  54.00-107.71  116
  6  \w    146.00 179.00   0.50    1.98    --   90.00  53.00 -55.44   66
  7  \w     68.00  99.00   0.50    1.98    --   90.00  54.00-107.71   62
  8  \w      2.00  35.00   0.50    1.98    --   90.00  43.00 -73.54   66
  9  \w     55.00  81.00   0.50    1.98    --   90.00  53.00-156.34   52
 10  \w    119.00 178.00   0.50    1.98    --   90.00  53.00-156.34  118
 11  \w     71.00  96.00   0.50    1.98    --   90.00  54.00 132.46   50
 12  \w     68.00  94.00   0.50    1.98    --   90.00  53.00 -55.44   52
 13  \w     22.00  52.00   0.50    1.98    --   90.00  53.00 -55.44   60
 14  \w     15.00  41.00   0.50    1.98    --   90.00  54.00-107.71   52
 15  \w     37.00  68.00   0.50    1.98    --   90.00  39.00-123.49   62
 16  \w    132.00 178.00   0.50    1.98    --   90.00  39.00-123.49   92
 17  \w     19.00  45.00   0.50    1.98    --   90.00  46.00-150.00   52
 18  \w     99.00 125.00   0.50    1.98    --   90.00  46.00-150.00   52
 19  \w    145.00 179.00   0.50    1.98    --   90.00  52.00  85.24   68
 20  \w     42.00  68.00   0.50    1.98    --   90.00  43.00 -73.54   52
 21  \w      1.00 128.00   0.50    1.98    --   90.00  46.00   0.00  254
 22  \w    133.00 179.00   0.50    1.98    --   90.00  46.00   0.00   92
 23  \w    117.00 143.00   0.50    1.98    --   90.00  46.00-180.00   52
 24  \w     96.00 121.00   0.50    1.98    --   90.00   9.00 120.00   50
 25  \w    134.00 160.00   0.50    1.98    --   90.00   9.00 120.00   52
 26  \w     13.00  43.00   0.50    1.98    --   90.00  37.00 -30.00   60
 27  \w     77.00 112.00   0.50    1.98    --   90.00  37.00 -30.00   70
 28  \w      2.00  31.00   0.50    1.98    --   90.00  39.00-123.49   58
 29  \w    113.00 169.00   0.50    1.98    --   90.00  55.00  61.87  112
 30  \w     16.00  42.00   0.50    1.98    --   90.00  55.00 117.42   52
 31  \w     99.00 135.00   0.50    1.98    --   90.00  18.00 150.00   72
 32  \w    112.00 161.00   0.50    1.98    --   90.00  55.00 117.42   98
 33  \w    149.00 178.00   0.50    1.98    --   90.00  54.00 132.46   58
 34  \w      1.00  94.00   0.50    1.98    --   90.00  18.00 150.00  186
 35  \w      7.00  33.00   0.50    1.98    --   90.00  51.00  16.91   52
 36  \w    134.00 168.00   0.50    1.98    --   90.00  51.00  16.91   68
 37  \w     46.00 114.00   0.50    1.98    --   90.00  37.00 -90.00  136
 38  \w    105.00 130.00   0.50    1.98    --   90.00  37.00  90.00   50
 39  \w     28.00  54.00   0.50    1.98    --   90.00  46.00 -60.00   52
 40  \w    133.00 159.00   0.50    1.98    --   90.00  46.00 -60.00   52
 41  \w      1.00  83.00   0.50    1.98    --   90.00  52.00  85.24  164
 42  \w    136.00 167.00   0.50    1.98    --   90.00  37.00 -30.00   62
 43  \w      8.00 126.00   0.50    1.98    --   90.00  28.00 -60.00  236
 44  \w    104.00 130.00   0.50    1.98    --   90.00  54.00 132.46   52
 45  \w      4.00  81.00   0.50    1.98    --   90.00  55.00  61.87  154
 46  \w     71.00  97.00   0.50    1.98    --   90.00  18.00 -30.00   52
 47  \w    136.00 162.00   0.50    1.98    --   90.00  18.00 -30.00   52
 48  \w    132.00 175.00   0.50    1.98    --   90.00  37.00-150.00   86
 49  \w     84.00 110.00   0.50    1.98    --   90.00  46.00-180.00   52
 50  \w    121.00 177.00   0.50    1.98    --   90.00  55.00-131.86  112
 51  \w    140.00 173.00   0.50    1.98    --   90.00  50.00 -68.06   66
 52  \w     88.00 114.00   0.50    1.98    --   90.00  55.00-131.86   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1045695000
_diffrn_orient_matrix_UB_12      -0.0131296000
_diffrn_orient_matrix_UB_13      0.0475484000
_diffrn_orient_matrix_UB_21      -0.0788715000
_diffrn_orient_matrix_UB_22      -0.0991661000
_diffrn_orient_matrix_UB_23      -0.0614689000
_diffrn_orient_matrix_UB_31      0.0756709000
_diffrn_orient_matrix_UB_32      -0.0817919000
_diffrn_orient_matrix_UB_33      0.0529240000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            36384
_diffrn_reflns_point_group_measured_fraction_full 0.821
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_theta_full        66.559
_diffrn_reflns_theta_max         66.559
_diffrn_reflns_theta_min         3.707
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.78a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 4127 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1044
_refine_ls_number_reflns         12156
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0815P)^2^+1.6525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1667
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.663
_reflns_Friedel_fraction_max     0.663
_reflns_number_gt                11191
_reflns_number_total             12156
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06234h2.cif
_cod_data_source_block           exp_3578
_cod_depositor_comments
'Adding full bibliography for 1568045--1568046.cif.'
_cod_database_code               1568045
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O '
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.758
_reflns_odcompleteness_completeness 96.85
_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 C(H,H,H,H,H,H) groups
2. Rigid bond restraints
 C3, C02X, C02Y, C1A, C1, C2A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C3) \\sim Ueq, Uanis(C02X) \\sim Ueq, Uanis(C02Y) \\sim Ueq, Uanis(C1)
\\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C2A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C1A)=Sof(H1AB)=
 Sof(H1AC)=Sof(H2AE)=Sof(H2AF)=Sof(H2AG)=1-FVAR(1)
 Sof(C02X)=Sof(H0AA)=Sof(HQ)=Sof(C02Y)=Sof(H1AA)=Sof(HR)=Sof(C1)=Sof(H1A)=
 Sof(H1B)=Sof(H2AB)=Sof(H2AC)=Sof(H2AD)=FVAR(1)
 Fixed X: H2AB(1.42937) H2AC(1.414619) H2AD(1.53385) H2AE(1.36853)
 H2AF(1.49234) H2AG(1.49692)
 Fixed Y: H2AB(0.12427) H2AC(0.105321) H2AD(0.188311) H2AE(0.109509)
 H2AF(0.19612) H2AG(0.11747)
 Fixed Z: H2AB(1.079589) H2AC(1.167121) H2AD(1.15662) H2AE(1.139729)
 H2AF(1.185941) H2AG(1.110861)
5.a Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B), C00L(H00C,H00D), C00P(H00E,H00F), C00X(H00G,H00H), C00Z(H00I,
 H00J), C012(H01A,H01B), C01D(H01K,H01L), C01E(H01C,H01D), C01I(H01O,H01P),
 C01K(H01Q,H01R), C01O(H01E,H01F), C01T(H01G,H01H), C020(H3AA,HA), C021(H4AA,
 HB), C022(H5AA,HC), C023(H6AA,HD), C027(H02A,H02B), C029(H02C,H02D), C02A(H8AA,
 HG), C02B(H9AA,HH), C02E(H02E,H02F), C02F(H1BA,HI), C02H(H02G,H02H), C02K(H02O,
 H02P), C02M(H02R,H02S), C02Q(H4BA,HN), C02S(H02V,H02W), C02U(H02Y,HO),
 C02W(H02,HP), C02X(H0AA,HQ), C02Y(H1AA,HR), C1(H1A,H1B), C3(H3A,H3B), C4(H4A,
 H4B), C1A(H1AB,H1AC)
5.b Aromatic/amide H refined with riding coordinates:
 C00R(H00R), C00Y(H00Y), C014(H014), C015(H015), C016(H016), C017(H017),
 C018(H018), C01A(H01I), C01B(H01J), C01F(H01M), C01L(H01S), C01M(H01T),
 C01N(H01N), C01P(H01U), C01V(H01V), C01W(H01W), C01Y(H01Z), C026(H026),
 C028(H028), C02D(H0BA), C02L(H02Q), C02P(H02T), C02R(H02U), C02T(H02X),
 C02V(H02Z), C02Z(H2AA), C030(H030), C032(H032)
5.c Idealised Me refined as rotating group:
 C01Q(H01X,H01Y,H), C025(H7AA,HE,HF), C02G(H2BA,HJ,HK), C02I(H02I,H02J,H02K),
 C02J(H02L,H02M,H02N), C02O(H3BA,HL,HM), C031(H03A,H03B,H03C)
;
_shelx_res_checksum              94857
_shelx_hkl_checksum              18913
_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 1.883
_oxdiff_exptl_absorpt_empirical_full_min 0.712