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_1567641
_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      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_creation_date             2022-01-20
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-06-02 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                91.523(4)
_cell_angle_beta                 91.016(4)
_cell_angle_gamma                93.880(2)
_cell_formula_units_Z            2
_cell_length_a                   6.36017(18)
_cell_length_b                   7.8529(2)
_cell_length_c                   20.1551(10)
_cell_measurement_reflns_used    16122
_cell_measurement_temperature    129(14)
_cell_measurement_theta_max      74.2050
_cell_measurement_theta_min      4.3050
_cell_volume                     1003.81(6)
_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      129(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.967
_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     10.00  35.00   0.50    0.51    --   14.00  29.00  -9.83   50
  2  \w     11.00  36.00   0.50    0.51    --   18.00  28.00   3.95   50
  3  \w     10.00  35.00   0.50    0.51    --   14.00  29.00  33.91   50
  4  \w     15.00  41.00   0.50    0.51    --   18.00  28.00  54.87   52
  5  \w     37.00  99.00   0.50    0.51    --   62.00  22.00-122.79  124
  6  \w     50.00  84.00   0.50    0.51    --   81.25  21.00-125.36   68
  7  \w     34.00  62.00   0.50    0.51    --   66.78  21.00-146.73   56
  8  \w     49.00  74.00   0.50    0.51    --   81.25  20.00-159.92   50
  9  \w     50.00  98.00   0.50    0.51    --   81.25  21.00  16.43   96
 10  \w     54.00 101.00   0.50    0.51    --   81.25  20.00  45.12   94
 11  \w     48.00  82.00   0.50    0.51    --   81.25  21.00 169.95   68
 12  \w    102.00 128.00   0.50    0.51    --   81.25  19.00 145.85   52
 13  \w    102.00 132.00   0.50    0.51    --   81.25  21.00 169.95   60
 14  \w     49.00  75.00   0.50    0.51    --   81.25  19.00 145.85   52
 15  \w     45.00 116.00   0.50    0.51    --   81.25  17.00 105.79  142
 16  \w     35.00  84.00   0.50    0.51    --   76.98   0.00  90.00   98
 17  \w     46.00  92.00   0.50    0.51    --   81.25  16.00 -19.52   92
 18  \w    106.00 131.00   0.50    0.51    --   81.25  16.00 -19.52   50
 19  \w     49.00 112.00   0.50    0.51    --   81.25  19.00 -82.52  126
 20  \w     35.00  93.00   0.50    0.51    --   76.98   0.00 -60.00  116
 21  \w     47.00 108.00   0.50    0.51    --   76.98   0.00   0.00  122
 22  \w     89.00 116.00   0.50    0.51    --   76.98   0.00  90.00   54
 23  \w    103.00 129.00   0.50    0.51    --   81.25  20.00-159.92   52
 24  \w     82.00 114.00   0.50    0.51    --   76.98   0.00-180.00   64
 25  \w     37.00  79.00   0.50    0.51    --   76.98   0.00-180.00   84
 26  \w     -8.00  40.00   0.50    0.51    --  -10.00  28.00-163.63   96
 27  \w    -52.00 -19.00   0.50    0.51    --  -59.37   0.00-180.00   66
 28  \w    -17.00  10.00   0.50    0.51    --  -26.00  51.00-116.71   54
 29  \w    -15.00  10.00   0.50    0.51    --  -22.00  44.00 -40.82   50
 30  \w   -101.00 -61.00   0.50    0.51    --  -59.37   0.00-180.00   80
 31  \w   -101.00 -57.00   0.50    0.51    --  -59.37   0.00 -90.00   88
 32  \w    -51.00 -18.00   0.50    0.51    --  -59.37   0.00 -90.00   66
 33  \w   -100.00 -75.00   0.50    0.51    --  -59.37   0.00   0.00   50
 34  \w   -100.00 -72.00   0.50    0.51    --  -59.37   0.00 150.00   56
 35  \w    -56.00 -31.00   0.50    0.51    --  -50.00 -24.00 111.42   50
 36  \w    -44.00 -19.00   0.50    0.51    --  -26.00 -27.00 143.97   50
 37  \w    -51.00 -26.00   0.50    0.51    --  -42.00 -25.00 -50.45   50
 38  \w    -48.00 -23.00   0.50    0.51    --  -34.00 -26.00 -70.83   50
 39  \w    -51.00 -26.00   0.50    0.51    --  -42.00 -25.00 -90.03   50
 40  \w    -56.00 -31.00   0.50    0.51    --  -50.00 -24.00-162.89   50
 41  \w    -56.00 -31.00   0.50    0.51    --  -50.00 -24.00-134.33   50
 42  \w    -85.00 -39.00   0.50    0.51    --  -59.37 125.00  60.00   92
 43  \w    -56.00 -31.00   0.50    0.51    --  -50.00 -24.00 131.29   50
 44  \w   -102.00 -66.00   0.50    0.51    --  -59.37 -15.00  60.00   72
 45  \w    -62.00 -37.00   0.50    0.51    --  -58.00 -23.00 158.17   50
 46  \w    -70.00 -41.00   0.50    0.51    --  -66.50 -22.00   6.14   58
 47  \w    -70.00 -40.00   0.50    0.51    --  -66.50 -22.00 -28.19   60
 48  \w    -70.00 -45.00   0.50    0.51    --  -66.50 -22.00 -57.23   50
 49  \w    -62.00 -37.00   0.50    0.51    --  -58.00 -23.00-173.77   50
 50  \w    -53.00 -27.00   0.50    0.51    --  -59.37 -15.00  60.00   52
 51  \w     37.00 112.00   0.50    0.51    --   81.25-129.00  99.07  150
 52  \w     38.00  98.00   0.50    0.51    --   76.98-125.00  60.00  120
 53  \w     36.00  95.00   0.50    0.51    --   76.98-125.00  30.00  118
 54  \w     41.00 109.00   0.50    0.51    --   76.98-125.00 150.00  136
 55  \w     35.00  81.00   0.50    0.51    --   76.98-125.00   0.00   92
 56  \w     79.00 109.00   0.50    0.51    --   76.98-125.00 -90.00   60
 57  \w     36.00  61.00   0.50    0.51    --   76.98-125.00-120.00   50
 58  \w     37.00  86.00   0.50    0.51    --   76.98-125.00-180.00   98
 59  \w     81.00 107.00   0.50    0.51    --   76.98-125.00-120.00   52
 60  \w     40.00  73.00   0.50    0.51    --   76.98-125.00-150.00   66
 61  \w     35.00  72.00   0.50    0.51    --   76.98-125.00 -90.00   74
 62  \w     76.00 101.00   0.50    0.51    --   76.98-125.00 -60.00   50
 63  \w     40.00  71.00   0.50    0.51    --   76.98-125.00 -60.00   62
 64  \w     40.00  76.00   0.50    0.51    --   81.25 -95.00-141.71   72
 65  \w     36.00 105.00   0.50    0.51    --   76.98-125.00 -30.00  138
 66  \w     18.00  70.00   0.50    0.51    --   59.80 -94.00 -60.00  104
 67  \w     18.00  71.00   0.50    0.51    --   59.80 -94.00   0.00  106
 68  \w     35.00  75.00   0.50    0.51    --   76.98-125.00 120.00   80
 69  \w     82.00 108.00   0.50    0.51    --   76.98-125.00 120.00   52
 70  \w     58.00  86.00   0.50    0.51    --   81.25 -83.00 148.25   56
 71  \w     19.00  70.00   0.50    0.51    --   59.80 -94.00  90.00  102
 72  \w     18.00  56.00   0.50    0.51    --   59.80 -94.00-120.00   76
;
_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      0.0116417000
_diffrn_orient_matrix_UB_12      0.1795205000
_diffrn_orient_matrix_UB_13      -0.0293002000
_diffrn_orient_matrix_UB_21      -0.0004440000
_diffrn_orient_matrix_UB_22      -0.0802674000
_diffrn_orient_matrix_UB_23      -0.0705869000
_diffrn_orient_matrix_UB_31      -0.2425434000
_diffrn_orient_matrix_UB_32      -0.0046598000
_diffrn_orient_matrix_UB_33      -0.0027763000
_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  0.0412
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20722
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.639
_diffrn_reflns_theta_min         2.193
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.973
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.415
_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    1.407
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.994
_refine_diff_density_min         -1.163
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0242P)^2^+1.3337P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0788
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3709
_reflns_number_total             3968
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03991e2.cif
_cod_data_source_block           cis_syn-(AA)-5
_cod_original_cell_volume        1003.82(6)
_cod_database_code               1567641
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C21 H29 Br1 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:
 C11(H11), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C25(H25A,H25B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              9233
_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 3.680
_oxdiff_exptl_absorpt_empirical_full_min 0.661