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_1567642
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-22
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.6941(3)
_cell_length_b                   8.2180(2)
_cell_length_c                   46.3766(14)
_cell_measurement_reflns_used    40320
_cell_measurement_temperature    296.0(3)
_cell_measurement_theta_max      72.8040
_cell_measurement_theta_min      2.8140
_cell_volume                     4075.8(2)
_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      air
_diffrn_ambient_temperature      296.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_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    -72.00 -18.00   0.50    2.00    --  -59.37  94.00 -61.00  108
  2  \w   -101.00 -75.00   0.50    2.00    --  -59.37   0.00  60.00   52
  3  \w   -101.00 -75.00   0.50    2.00    --  -59.37   0.00 -30.00   52
  4  \w    -85.00 -35.00   0.50    2.00    --  -59.37 125.00  90.00  100
  5  \w    -85.00 -35.00   0.50    2.00    --  -59.37 125.00-150.00  100
  6  \w   -101.00 -75.00   0.50    2.00    --  -59.37   0.00   0.00   52
  7  \w   -101.00 -75.00   0.50    2.00    --  -59.37   0.00-150.00   52
  8  \w     39.00 123.00   0.50    2.00    --   73.96  15.00  90.00  168
  9  \w     32.00  86.00   0.50    2.00    --   73.96 -94.00-150.00  108
 10  \w     32.00  86.00   0.50    2.00    --   73.96 -94.00 -30.00  108
 11  \w     32.00  86.00   0.50    2.00    --   73.96 -94.00 -90.00  108
 12  \w     39.00 124.00   0.50    2.00    --   74.41  15.00   0.00  170
 13  \w     33.00  87.00   0.50    2.00    --   74.41 -94.00  60.00  108
 14  \w    -50.00 -24.00   0.50    2.00    --  -42.00 -25.00 -71.28   52
 15  \w    -56.00 -31.00   0.50    2.00    --  -50.00 -24.00  17.92   50
 16  \w    -56.00 -31.00   0.50    2.00    --  -50.00 -24.00 104.27   50
 17  \w    -56.00 -31.00   0.50    2.00    --  -50.00 -24.00-169.84   50
 18  \w    -62.00 -37.00   0.50    2.00    --  -58.00 -23.00 -13.92   50
 19  \w    -62.00 -37.00   0.50    2.00    --  -58.00 -23.00-104.70   50
 20  \w   -101.00 -76.00   0.50    2.00    --  -59.37   0.00 -90.00   50
 21  \w   -100.00 -75.00   0.50    2.00    --  -59.37   0.00 120.00   50
 22  \w   -101.00 -76.00   0.50    2.00    --  -59.37   0.00 -30.00   50
 23  \w     68.00  93.00   0.50    2.00    --   60.10-125.00 -60.00   50
 24  \w    -68.00 -42.00   0.50    2.00    --  -66.50  83.00-150.29   52
 25  \w    -69.00 -35.00   0.50    2.00    --  -66.50  83.00  87.52   68
 26  \w    -62.00 -30.00   0.50    2.00    --  -66.50  82.00  -6.18   64
 27  \w    -71.00 -45.00   0.50    2.00    --  -66.50 -22.00 146.35   52
 28  \w    -70.00 -43.00   0.50    2.00    --  -66.50 -22.00  62.87   54
 29  \w     41.00  66.00   0.50    2.00    --   67.03  22.00  70.65   50
 30  \w     43.00  70.00   0.50    2.00    --   67.03  22.00-108.84   54
 31  \w     35.00  70.00   0.50    2.00    --   73.96-125.00  30.00   70
 32  \w     54.00  80.00   0.50    2.00    --   73.96 -94.00  60.00   52
 33  \w     55.00 107.00   0.50    2.00    --   73.96-125.00 -30.00  104
 34  \w     58.00  84.00   0.50    2.00    --   73.96-123.00 111.00   52
 35  \w     50.00  84.00   0.50    2.00    --   73.96 -94.00 150.00   68
 36  \w     32.00  57.00   0.50    2.00    --   73.96 -94.00-180.00   50
 37  \w     82.00 107.00   0.50    2.00    --   73.96-125.00  30.00   50
 38  \w     38.00 108.00   0.50    2.00    --   74.41-125.00 150.00  140
 39  \w     33.00  86.00   0.50    2.00    --   74.41   0.00-180.00  106
 40  \w     85.00 118.00   0.50    2.00    --   79.15  21.00-151.85   66
 41  \w     46.00  79.00   0.50    2.00    --   79.15  21.00-151.85   66
 42  \w     92.00 129.00   0.50    2.00    --   79.15-152.00 -92.06   74
 43  \w     61.00 121.00   0.50    2.00    --   79.15  17.00 -87.09  120
 44  \w     53.00  86.00   0.50    2.00    --   79.15-152.00 -92.06   66
 45  \w     34.00 107.00   0.50    2.00    --   79.15-115.00  59.45  146
 46  \w    -20.00   6.00   0.50    2.00    --  -26.00  56.00 121.28   52
 47  \w    -29.00   3.00   0.50    2.00    --  -34.00  59.00  90.45   64
 48  \w    -29.00   3.00   0.50    2.00    --  -34.00  59.00  34.32   64
 49  \w    -51.00 -24.00   0.50    2.00    --  -42.00 -25.00 -27.85   54
 50  \w    -56.00 -30.00   0.50    2.00    --  -50.00 -24.00 -56.23   52
 51  \w    -56.00 -30.00   0.50    2.00    --  -50.00 -24.00 -91.85   52
 52  \w    -62.00 -35.00   0.50    2.00    --  -58.00 -23.00 167.60   54
 53  \w    -62.00 -35.00   0.50    2.00    --  -58.00 -23.00-165.90   54
 54  \w    -62.00 -35.00   0.50    2.00    --  -58.00 -23.00  15.37   54
 55  \w    -62.00 -35.00   0.50    2.00    --  -58.00 -23.00  78.87   54
 56  \w   -101.00 -75.00   0.50    2.00    --  -59.37   0.00 -60.00   52
 57  \w   -101.00 -75.00   0.50    2.00    --  -59.37   0.00 150.00   52
 58  \w   -101.00 -75.00   0.50    2.00    --  -59.37   0.00  30.00   52
 59  \w   -101.00 -75.00   0.50    2.00    --  -59.37   0.00-180.00   52
 60  \w   -101.00 -75.00   0.50    2.00    --  -59.37   0.00 -90.00   52
 61  \w   -101.00 -75.00   0.50    2.00    --  -59.37   0.00  90.00   52
 62  \w    -71.00 -40.00   0.50    2.00    --  -66.50 -22.00-130.27   62
 63  \w     41.00  71.00   0.50    2.00    --   67.03  22.00 156.05   60
 64  \w     33.00 116.00   0.50    2.00    --   74.41   0.00-150.00  166
;
_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      0.0366851000
_diffrn_orient_matrix_UB_12      0.0777725000
_diffrn_orient_matrix_UB_13      0.0290266000
_diffrn_orient_matrix_UB_21      0.0428711000
_diffrn_orient_matrix_UB_22      0.1547863000
_diffrn_orient_matrix_UB_23      -0.0158609000
_diffrn_orient_matrix_UB_31      -0.1325216000
_diffrn_orient_matrix_UB_32      0.0718000000
_diffrn_orient_matrix_UB_33      0.0028766000
_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  0.0305
_diffrn_reflns_av_unetI/netI     0.0076
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            69471
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.231
_diffrn_reflns_theta_min         3.813
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.929
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
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    1.386
_exptl_crystal_description       plate
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.782
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0476P)^2^+3.2520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3775
_reflns_number_total             3965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03991e2.cif
_cod_data_source_block           trans_syn-(AA)-5
_cod_database_code               1567642
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'Br O4 C21 H29'
_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:
 C10(H10), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C19(H19A,H19B), C20(H20A,H20B)
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:
 C8(H8A,H8B,H8C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              52232
_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 1.616
_oxdiff_exptl_absorpt_empirical_full_min 0.701