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_1572046
_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         'C H2 Cl2, C29 H33 N7 O2'
_chemical_formula_sum            'C30 H35 Cl2 N7 O2'
_chemical_formula_weight         596.55
_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             2024-03-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-03-07 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.4350(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.11960(10)
_cell_length_b                   10.25230(10)
_cell_length_c                   15.3641(2)
_cell_measurement_reflns_used    18506
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      76.6170
_cell_measurement_theta_min      2.9970
_cell_volume                     1512.21(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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (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 0.992
_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     34.00  77.00   0.50    0.05    --   47.53  57.00  90.00   86
  2  \w     83.00 177.00   0.50    0.20    --  104.75  77.00 -60.00  188
  3  \w     83.00 177.00   0.50    0.20    --  104.75  77.00 -90.00  188
  4  \w     32.00 120.00   0.50    0.05    --   47.53  62.00-175.00  176
  5  \w     89.00 177.00   0.50    0.20    --  104.75  62.00-175.00  176
  6  \w     91.00 177.00   0.50    0.20    --  104.75  57.00 -60.00  172
  7  \w     94.00 177.00   0.50    0.20    --  104.75  38.00 -30.00  166
  8  \w     91.00 177.00   0.50    0.20    --  104.75  57.00  90.00  172
  9  \w    -25.00  45.00   0.50    0.05    --   47.53 -38.00  90.00  140
 10  \w    -24.00  63.00   0.50    0.05    --   47.53 -62.00  46.00  174
 11  \w     33.00  75.00   0.50    0.20    --  104.75 -62.00  46.00   84
 12  \w     33.00  68.00   0.50    0.20    --  104.75 -57.00 -30.00   70
 13  \w     33.00  68.00   0.50    0.20    --  104.75 -57.00 -90.00   70
 14  \w     33.00  68.00   0.50    0.20    --  104.75 -57.00-120.00   70
 15  \w     33.00  68.00   0.50    0.20    --  104.75 -57.00-180.00   70
 16  \w     33.00 111.00   0.50    0.20    --  104.75-125.00  60.00  156
 17  \w     33.00 111.00   0.50    0.20    --  104.75-125.00 120.00  156
 18  \w     33.00 106.00   0.50    0.20    --  104.75 -99.00 150.00  146
 19  \w     33.00 106.00   0.50    0.20    --  104.75 -99.00 120.00  146
 20  \w     33.00 106.00   0.50    0.20    --  104.75 -99.00-150.00  146
 21  \w   -103.00 -32.00   0.50    0.20    -- -104.00  77.00 -60.00  142
 22  \w    -63.00  25.00   0.50    0.05    --  -47.53  62.00-175.00  176
 23  \w    -71.00 -32.00   0.50    0.20    -- -104.00  62.00-175.00   78
 24  \w    -64.00 -32.00   0.50    0.20    -- -104.00  57.00   0.00   64
 25  \w   -103.00 -32.00   0.50    0.20    -- -104.00  77.00  60.00  142
 26  \w   -103.00 -32.00   0.50    0.20    -- -104.00  77.00 120.00  142
 27  \w    -64.00 -32.00   0.50    0.20    -- -104.00  57.00 150.00   64
 28  \w   -175.00 -93.00   0.50    0.20    -- -104.00 -19.00 120.00  164
 29  \w   -175.00 -88.00   0.50    0.20    -- -104.00 -62.00  46.00  174
 30  \w   -119.00 -32.00   0.50    0.05    --  -47.53 -62.00  46.00  174
 31  \w   -119.00 -34.00   0.50    0.05    --  -47.53 -57.00 -60.00  170
 32  \w   -175.00 -82.00   0.50    0.20    -- -104.00 -77.00 -30.00  186
 33  \w   -175.00 -90.00   0.50    0.20    -- -104.00 -57.00 -60.00  170
 34  \w   -175.00 -93.00   0.50    0.20    -- -104.00 -19.00 -30.00  164
 35  \w   -175.00 -93.00   0.50    0.20    -- -104.00 -19.00 -60.00  164
 36  \w   -175.00 -93.00   0.50    0.20    -- -104.00 -38.00 -90.00  164
 37  \w   -175.00 -93.00   0.50    0.20    -- -104.00 -38.00-120.00  164
 38  \w   -119.00 -73.00   0.50    0.05    --  -47.53-125.00-150.00   92
;
_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      -0.0609139000
_diffrn_orient_matrix_UB_12      -0.0470917000
_diffrn_orient_matrix_UB_13      0.0745916000
_diffrn_orient_matrix_UB_21      -0.1208395000
_diffrn_orient_matrix_UB_22      0.0978340000
_diffrn_orient_matrix_UB_23      -0.0346535000
_diffrn_orient_matrix_UB_31      -0.0862512000
_diffrn_orient_matrix_UB_32      -0.1038685000
_diffrn_orient_matrix_UB_33      -0.0664088000
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29091
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.632
_diffrn_reflns_theta_min         3.032
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50989
_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    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2610 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         6207
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0711P)^2^+0.7308P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1290
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                5945
_reflns_number_total             6207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03506b2.cif
_cod_data_source_block           5w-20240307-1_auto
_cod_depositor_comments
'Adding full bibliography for 1572045--1572046.cif.'
_cod_database_code               1572046
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N Cl'
_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.a Secondary CH2 refined with riding coordinates:
 C012(H01P,H01Q)
2.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00T(H00T), C00U(H00U), C00W(H00W)
2.c Idealised Me refined as rotating group:
 C00X(H00A,H00B,H00C), C00Y(H00D,H00E,H00F), C00Z(H00H,H00I,H00J), C010(H01A,
 H01B,H01C), C011(H01D,H01E,H01F), C013(H01G,H01H,H01I), C014(H01J,H01K,H01L),
 C015(H01M,H01N,H01O)
;
_shelx_res_checksum              96910
_shelx_hkl_checksum              31007
_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 1.753
_oxdiff_exptl_absorpt_empirical_full_min 0.525