Inherently chiral nor-heteracalixarenes: design and synthesis <i>via</i> enantioselective intramolecular Suzuki-Miyaura reaction.
Jiang, Yi-Fan; Tong, Shuo; Zhu, Jieping; Wang, Mei-Xiang; Chemical science 15 (2024) 12517–12522; doi:10.1039/d4sc03506b

data_1572045
_publ_section_title
;
 Inherently chiral nor-heteracalixarenes: design and synthesis <i>via</i>
 enantioselective intramolecular Suzuki-Miyaura reaction.
;
_journal_issue                   31
_journal_name_full               'Chemical science'
_journal_page_first              12517
_journal_page_last               12522
_journal_paper_doi               10.1039/d4sc03506b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C27 H30 N8 O'
_chemical_formula_sum            'C27 H30 N8 O'
_chemical_formula_weight         482.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-02-18 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.053(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3425(2)
_cell_length_b                   12.0823(2)
_cell_length_c                   10.7603(2)
_cell_measurement_reflns_used    14332
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      77.1510
_cell_measurement_theta_min      4.3640
_cell_volume                     1254.86(4)
_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 1.000
_diffrn_measured_fraction_theta_max 0.983
_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    -64.00  24.00   0.50    0.35    --  -48.26  63.00 -88.00  176
  2  \w   -119.00 -32.00   0.50    0.35    --  -48.26 -63.00 134.00  174
  3  \w    -72.00 -32.00   0.50    1.39    -- -104.00  63.00 -88.00   80
  4  \w   -175.00 -88.00   0.50    1.39    -- -104.00 -63.00 134.00  174
  5  \w     35.00  76.00   0.50    1.39    --  106.93 -63.00 134.00   82
  6  \w     91.00 178.00   0.50    1.39    --  106.93  63.00 -88.00  174
  7  \w   -119.00 -74.00   0.50    0.35    --  -48.26-125.00 -60.00   90
  8  \w   -120.00 -38.00   0.50    0.35    --  -48.26 -38.00 -30.00  164
  9  \w   -119.00 -74.00   0.50    0.35    --  -48.26-125.00-150.00   90
 10  \w   -119.00 -74.00   0.50    0.35    --  -48.26-125.00 120.00   90
 11  \w    -41.00  24.00   0.50    0.35    --  -48.26  38.00-120.00  130
 12  \w   -120.00 -38.00   0.50    0.35    --  -48.26 -38.00  30.00  164
 13  \w    -24.00  26.00   0.50    0.35    --  -48.26  19.00  30.00  100
 14  \w    -23.00  64.00   0.50    0.35    --   48.26 -63.00 134.00  174
 15  \w     32.00 121.00   0.50    0.35    --   48.26  63.00 -88.00  178
 16  \w   -111.00 -32.00   0.50    1.39    -- -104.00 125.00  60.00  158
 17  \w   -111.00 -32.00   0.50    1.39    -- -104.00 125.00-180.00  158
 18  \w   -175.00 -90.00   0.50    1.39    -- -104.00 -57.00   0.00  170
 19  \w   -103.00 -32.00   0.50    1.39    -- -104.00  77.00 120.00  142
 20  \w   -175.00 -82.00   0.50    1.39    -- -104.00 -77.00  60.00  186
 21  \w   -175.00 -93.00   0.50    1.39    -- -104.00 -19.00 -30.00  164
 22  \w   -175.00 -93.00   0.50    1.39    -- -104.00 -19.00  30.00  164
 23  \w   -175.00 -90.00   0.50    1.39    -- -104.00 -57.00  30.00  170
 24  \w   -103.00 -32.00   0.50    1.39    -- -104.00  77.00-120.00  142
 25  \w   -103.00 -32.00   0.50    1.39    -- -104.00  77.00  30.00  142
 26  \w   -175.00 -93.00   0.50    1.39    -- -104.00 -38.00  90.00  164
 27  \w    -64.00 -32.00   0.50    1.39    -- -104.00  57.00 -90.00   64
 28  \w    -64.00 -32.00   0.50    1.39    -- -104.00  57.00 -60.00   64
 29  \w     35.00  68.00   0.50    1.39    --  106.93 -57.00   0.00   66
 30  \w     96.00 178.00   0.50    1.39    --  106.93  38.00-180.00  164
 31  \w     35.00 106.00   0.50    1.39    --  106.93 -99.00-120.00  142
 32  \w     35.00  68.00   0.50    1.39    --  106.93 -57.00 -90.00   66
 33  \w     96.00 178.00   0.50    1.39    --  106.93  38.00-150.00  164
 34  \w     35.00 106.00   0.50    1.39    --  106.93 -99.00  30.00  142
 35  \w     35.00  68.00   0.50    1.39    --  106.93 -57.00  90.00   66
 36  \w     85.00 178.00   0.50    1.39    --  106.93  77.00 -30.00  186
 37  \w     85.00 178.00   0.50    1.39    --  106.93  77.00   0.00  186
 38  \w     35.00  68.00   0.50    1.39    --  106.93 -57.00-120.00   66
;
_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      0.1173794000
_diffrn_orient_matrix_UB_12      0.0864129000
_diffrn_orient_matrix_UB_13      0.0432836000
_diffrn_orient_matrix_UB_21      -0.0385045000
_diffrn_orient_matrix_UB_22      0.0367031000
_diffrn_orient_matrix_UB_23      -0.1459973000
_diffrn_orient_matrix_UB_31      -0.1010785000
_diffrn_orient_matrix_UB_32      0.0862520000
_diffrn_orient_matrix_UB_33      0.0187964000
_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  0.0372
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23451
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.012
_diffrn_reflns_theta_min         4.403
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83286
_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 light colourless'
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 2171 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         5147
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0475P)^2^+0.1914P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                4942
_reflns_number_total             5147
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03506b2.cif
_cod_data_source_block           14-tm-20230310_auto
_cod_depositor_comments
'Adding full bibliography for 1572045--1572046.cif.'
_cod_database_code               1572045
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N'
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00I(H00I), C00K(H00K), C00M(H00M), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T)
2.b Idealised Me refined as rotating group:
 C00U(H00A,H00B,H00C), C00V(H00D,H00E,H00F), C00W(H00H,H00J,H00L), C00X(H00N,
 H00O,H00U), C00Y(H00V,H00W,H00X), C00Z(H00Y,H,HA), C010(H01A,H01B,H01C)
;
_shelx_res_checksum              50184
_shelx_hkl_checksum              62350
_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 1.740
_oxdiff_exptl_absorpt_empirical_full_min 0.311