Decoded fingerprints of hyperresponsive, expanding product space: polyether cascade cyclizations as tools to elucidate supramolecular catalysis
Chen, Hao; Li, Tian-Ren; Sakai, Naomi; Besnard, Celine; Guénée, Laure; Pupier, Marion; Viger-Gravel, Jasmine; Tiefenbacher, Konrad; Matile, Stefan; Chemical Science 13 (2022) 10273–10280; doi:10.1039/D2SC03991E

data_1567645
_publ_section_title
;
 Decoded fingerprints of hyperresponsive, expanding product space:
 polyether cascade cyclizations as tools to elucidate supramolecular
 catalysis
;
_journal_issue                   35
_journal_name_full               'Chemical Science'
_journal_page_first              10273
_journal_page_last               10280
_journal_paper_doi               10.1039/D2SC03991E
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C21 H29 Br O4'
_chemical_formula_sum            'C21 H29 Br O4'
_chemical_formula_weight         425.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-20
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2022-06-02 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.447(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0432(5)
_cell_length_b                   7.0309(3)
_cell_length_c                   21.1186(8)
_cell_measurement_reflns_used    19361
_cell_measurement_temperature    119.99(10)
_cell_measurement_theta_max      74.2960
_cell_measurement_theta_min      3.1480
_cell_volume                     2050.61(14)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_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      4.00  29.00   0.50    4.00    --    2.00  33.00 -67.11   50
  2  \w      5.00  31.00   0.50    4.00    --    2.00  33.00 -38.79   52
  3  \w      8.00  33.00   0.50    4.00    --   10.00  30.00 -78.05   50
  4  \w     15.00  41.00   0.50    4.00    --   22.00  27.00 -42.80   52
  5  \w     13.00  40.00   0.50    4.00    --   22.00  27.00   0.06   54
  6  \w    -48.00 -23.00   0.50    4.00    --  -34.00 -26.00 148.13   50
  7  \w    -50.00 -24.00   0.50    4.00    --  -42.00 -25.00  95.04   52
  8  \w    -51.00 -26.00   0.50    4.00    --  -42.00 -25.00-179.85   50
  9  \w    -56.00 -30.00   0.50    4.00    --  -50.00 -24.00 126.84   52
 10  \w    -56.00 -30.00   0.50    4.00    --  -50.00 -24.00-154.30   52
 11  \w    -61.00 -36.00   0.50    4.00    --  -58.00 -23.00-178.30   50
 12  \w   -100.00 -75.00   0.50    4.00    --  -59.37   0.00  60.00   50
 13  \w    -92.00 -54.00   0.50    4.00    --  -59.37   0.00 150.00   76
 14  \w    -50.00 -18.00   0.50    4.00    --  -59.37   0.00 150.00   64
 15  \w    -98.00 -32.00   0.50    4.00    --  -59.37 -15.00 -90.00  132
 16  \w     36.00  62.00   0.50    4.00    --   59.80 -94.00-120.00   52
 17  \w     21.00  72.00   0.50    4.00    --   59.80 -94.00  90.00  102
 18  \w     19.00  67.00   0.50    4.00    --   59.80 -94.00  30.00   96
 19  \w     24.00  69.00   0.50    4.00    --   59.80 -94.00 150.00   90
 20  \w     38.00  66.00   0.50    4.00    --   59.80 -94.00 -30.00   56
 21  \w    -88.00 -62.00   0.50    4.00    --  -66.50 -18.00 124.96   52
 22  \w    -70.00 -45.00   0.50    4.00    --  -66.50 -22.00  92.99   50
 23  \w     93.00 118.00   0.50    4.00    --   66.78  21.00 -78.76   50
 24  \w     41.00  67.00   0.50    4.00    --   66.78  22.00 -44.85   52
 25  \w     56.00  81.00   0.50    4.00    --   76.98 -94.00 -30.00   50
 26  \w     35.00  77.00   0.50    4.00    --   76.98-125.00   0.00   84
 27  \w     85.00 110.00   0.50    4.00    --   76.98-125.00  30.00   50
 28  \w     36.00  88.00   0.50    4.00    --   76.98 -94.00  90.00  104
 29  \w     35.00  76.00   0.50    4.00    --   76.98   0.00  30.00   82
 30  \w     79.00 104.00   0.50    4.00    --   76.98   0.00  30.00   50
 31  \w     80.00 105.00   0.50    4.00    --   76.98-125.00 120.00   50
 32  \w     35.00  61.00   0.50    4.00    --   76.98-125.00 120.00   52
 33  \w     35.00  76.00   0.50    4.00    --   76.98-125.00-180.00   82
 34  \w     65.00  91.00   0.50    4.00    --   76.98-125.00 150.00   52
 35  \w     38.00  63.00   0.50    4.00    --   76.98-125.00 150.00   50
 36  \w     38.00  77.00   0.50    4.00    --   76.98 -94.00 -90.00   78
 37  \w     40.00  87.00   0.50    4.00    --   76.98 -94.00   0.00   94
 38  \w     39.00  87.00   0.50    4.00    --   76.98-125.00  60.00   96
 39  \w     35.00  62.00   0.50    4.00    --   76.98-125.00  90.00   54
 40  \w     60.00 110.00   0.50    4.00    --   76.98-125.00-150.00  100
 41  \w     42.00  72.00   0.50    4.00    --   76.98 -94.00-120.00   60
 42  \w     76.00 102.00   0.50    4.00    --   76.98  15.00-180.00   52
 43  \w     96.00 121.00   0.50    4.00    --   81.25  16.00  88.04   50
 44  \w     50.00  85.00   0.50    4.00    --   81.25  16.00  88.04   70
 45  \w     65.00  95.00   0.50    4.00    --   81.25  20.00 -74.40   60
 46  \w     99.00 125.00   0.50    4.00    --   81.25  14.00 128.47   52
 47  \w     42.00 120.00   0.50    4.00    --   81.25   5.00 -75.11  156
 48  \w     48.00  83.00   0.50    4.00    --   81.25  21.00 -95.57   70
 49  \w     35.00 106.00   0.50    4.00    --   81.25-111.00 -51.53  142
 50  \w     40.00  66.00   0.50    4.00    --   81.25 -71.00  43.09   52
 51  \w     48.00 126.00   0.50    4.00    --   81.25  21.00   9.11  156
 52  \w     35.00 106.00   0.50    4.00    --   81.25-114.00  65.59  142
 53  \w     48.00  81.00   0.50    4.00    --   81.25  21.00 -26.16   66
 54  \w    107.00 132.00   0.50    4.00    --   81.25  20.00 -74.40   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1035401000
_diffrn_orient_matrix_UB_12      0.0671292000
_diffrn_orient_matrix_UB_13      0.0278184000
_diffrn_orient_matrix_UB_21      -0.0360017000
_diffrn_orient_matrix_UB_22      0.0826348000
_diffrn_orient_matrix_UB_23      0.0589808000
_diffrn_orient_matrix_UB_31      0.0207865000
_diffrn_orient_matrix_UB_32      -0.1914461000
_diffrn_orient_matrix_UB_33      0.0353237000
_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  0.0285
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30520
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.569
_diffrn_reflns_theta_min         3.200
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.911
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.435
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.378
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.451
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0323P)^2^+1.2040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0691
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3796
_reflns_number_total             4126
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03991e2.cif
_cod_data_source_block           cis_anti-(AB)-4
_cod_database_code               1567645
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C21 H29 Br O4'
_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 Ternary CH refined with riding coordinates:
 C13(H13), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C23(H23A,H23B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C18(H18A,H18B,H18C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              56954
_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 1.400
_oxdiff_exptl_absorpt_empirical_full_min 0.783