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_1567647
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-01-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-06-02 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                69.1422(14)
_cell_angle_beta                 81.6780(12)
_cell_angle_gamma                84.3027(12)
_cell_formula_units_Z            2
_cell_length_a                   7.44418(10)
_cell_length_b                   11.53654(18)
_cell_length_c                   12.84945(19)
_cell_measurement_reflns_used    18859
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      73.9720
_cell_measurement_theta_min      3.7060
_cell_volume                     1018.98(3)
_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 1.3 (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 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(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 0.999
_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      7.00  32.00   0.50    0.20    --    4.00  31.00  80.00   50
  2  \w      9.00  34.00   0.50    0.20    --    8.00  30.00 -61.19   50
  3  \w     11.00  38.00   0.50    0.20    --   12.00  29.00 -87.63   54
  4  \w      4.00  32.00   0.50    0.20    --    0.00  32.00-154.89   56
  5  \w    -56.00 -26.00   0.50    0.20    --  -64.50  73.00   3.64   60
  6  \w    -91.00 -38.00   0.50    0.20    --  -57.30   0.00 -90.00  106
  7  \w    -76.00 -36.00   0.50    0.20    --  -57.30   0.00 -30.00   80
  8  \w    -83.00 -18.00   0.50    0.20    --  -57.30   0.00  30.00  130
  9  \w    -95.00 -60.00   0.50    0.20    --  -57.30   0.00 120.00   70
 10  \w    -57.00 -31.00   0.50    0.20    --  -57.30   0.00 120.00   52
 11  \w      2.00  29.00   0.50    0.20    --   -4.00  34.00 165.74   54
 12  \w      2.00  28.00   0.50    0.20    --   -4.00  33.00  22.86   52
 13  \w      1.00  27.00   0.50    0.20    --   -4.00  33.00 -15.26   52
 14  \w      1.00  26.00   0.50    0.20    --   -4.00  34.00 -78.57   50
 15  \w    -55.00 -28.00   0.50    0.20    --  -44.00 -24.00 103.69   54
 16  \w    -48.00 -19.00   0.50    0.20    --  -28.00 -26.00 161.42   58
 17  \w    -55.00 -29.00   0.50    0.20    --  -57.30 136.00  27.00   52
 18  \w    -86.00 -60.00   0.50    0.20    --  -57.30 136.00  27.00   52
 19  \w    -56.00 -31.00   0.50    0.20    --  -44.00 -24.00  61.23   50
 20  \w    -45.00 -19.00   0.50    0.20    --  -28.00 -26.00-120.86   52
 21  \w    -44.00 -19.00   0.50    0.20    --  -24.00 -27.00 -86.95   50
 22  \w    -51.00 -26.00   0.50    0.20    --  -36.00 -25.00 -54.53   50
 23  \w    -62.00 -35.00   0.50    0.20    --  -52.00 -23.00 -40.57   54
 24  \w    -71.00 -46.00   0.50    0.20    --  -64.50 -22.00 -94.49   50
 25  \w    -71.00 -46.00   0.50    0.20    --  -64.50 -22.00-138.97   50
 26  \w    -71.00 -46.00   0.50    0.20    --  -64.50 -22.00 -13.51   50
 27  \w    -70.00 -44.00   0.50    0.20    --  -64.50 -22.00   1.31   52
 28  \w    -71.00 -45.00   0.50    0.20    --  -64.50 -22.00  30.62   52
 29  \w    -61.00 -35.00   0.50    0.20    --  -52.00 -23.00  80.17   52
 30  \w     44.00  86.00   0.50    0.20    --   67.73  21.00 -51.35   84
 31  \w     46.00  74.00   0.50    0.20    --   67.73  21.00 -82.10   56
 32  \w     52.00 118.00   0.50    0.20    --   81.25  20.00-160.57  132
 33  \w     52.00 130.00   0.50    0.20    --   81.25  20.00 -98.66  156
 34  \w     39.00  90.00   0.50    0.20    --   67.73  20.00  -4.35  102
 35  \w     90.00 127.00   0.50    0.20    --   81.25  20.00  39.35   74
 36  \w     52.00  84.00   0.50    0.20    --   81.25  20.00  39.35   64
 37  \w     43.00  86.00   0.50    0.20    --   75.00  15.00   0.00   86
 38  \w     40.00  77.00   0.50    0.20    --   67.73  20.00  81.75   74
 39  \w     54.00 122.00   0.50    0.20    --   81.25  20.00  97.27  136
 40  \w     98.00 123.00   0.50    0.20    --   81.25  18.00 176.71   50
 41  \w     47.00  74.00   0.50    0.20    --   81.25  18.00 176.71   54
 42  \w     89.00 122.00   0.50    0.20    --   75.00  15.00   0.00   66
 43  \w     67.00 117.00   0.50    0.20    --   77.04   0.00   0.00  100
 44  \w     38.00  63.00   0.50    0.20    --   77.04   0.00   0.00   50
 45  \w     38.00  64.00   0.50    0.20    --   77.04   0.00  90.00   52
 46  \w     74.00 117.00   0.50    0.20    --   77.04   0.00  90.00   86
 47  \w     38.00  63.00   0.50    0.20    --   77.04   0.00 -90.00   50
 48  \w     67.00 113.00   0.50    0.20    --   77.04   0.00 -90.00   92
 49  \w     38.00 116.00   0.50    0.20    --   77.04   0.00-180.00  156
 50  \w     31.00  56.00   0.50    0.20    --   76.00 -56.00 -84.07   50
 51  \w     87.00 114.00   0.50    0.20    --   81.25-129.00-135.38   54
 52  \w     37.00  79.00   0.50    0.20    --   81.25-129.00-135.38   84
 53  \w     35.00  66.00   0.50    0.20    --   77.04-125.00 -90.00   62
 54  \w     52.00 106.00   0.50    0.20    --   77.04-136.00 -36.00  108
 55  \w     71.00 106.00   0.50    0.20    --   75.00-125.00-150.00   70
 56  \w     35.00  63.00   0.50    0.20    --   75.00-125.00-150.00   56
 57  \w     78.00 103.00   0.50    0.20    --   75.00-125.00  30.00   50
 58  \w     35.00  96.00   0.50    0.20    --   77.04-125.00  90.00  122
 59  \w     40.00  75.00   0.50    0.20    --   77.04-125.00 120.00   70
 60  \w     43.00  71.00   0.50    0.20    --   77.04-132.00 140.00   56
 61  \w     83.00 112.00   0.50    0.20    --   77.04-132.00 140.00   58
 62  \w     63.00  88.00   0.50    0.20    --   77.04-125.00   0.00   50
 63  \w     35.00  61.00   0.50    0.20    --   77.04-125.00   0.00   52
 64  \w     37.00  63.00   0.50    0.20    --   75.00-125.00  30.00   52
 65  \w     69.00 110.00   0.50    0.20    --   81.25-123.00 -71.66   82
 66  \w     40.00  90.00   0.50    0.20    --   75.00-125.00-120.00  100
 67  \w     37.00  65.00   0.50    0.20    --   81.25-115.00 -96.61   56
 68  \w     35.00  61.00   0.50    0.20    --   81.25-123.00 -71.66   52
 69  \w     56.00  82.00   0.50    0.20    --   77.04 -94.00-150.00   52
 70  \w     39.00  64.00   0.50    0.20    --   77.04 -94.00   0.00   50
 71  \w     36.00 109.00   0.50    0.20    --   81.25-118.00  48.38  146
 72  \w     38.00 104.00   0.50    0.20    --   81.25-123.00 160.20  132
 73  \w     35.00  70.00   0.50    0.20    --   75.00 -94.00 150.00   70
 74  \w     27.00  53.00   0.50    0.20    --   60.47 -94.00 120.00   52
 75  \w     23.00  52.00   0.50    0.20    --   60.47 -94.00  60.00   58
 76  \w     23.00  54.00   0.50    0.20    --   60.47 -94.00 -60.00   62
 77  \w     45.00  70.00   0.50    0.20    --   81.25 -64.00 -73.32   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      -0.0168059000
_diffrn_orient_matrix_UB_12      -0.0400042000
_diffrn_orient_matrix_UB_13      0.1287474000
_diffrn_orient_matrix_UB_21      0.0642151000
_diffrn_orient_matrix_UB_22      0.1270633000
_diffrn_orient_matrix_UB_23      -0.0106524000
_diffrn_orient_matrix_UB_31      -0.1986328000
_diffrn_orient_matrix_UB_32      0.0522520000
_diffrn_orient_matrix_UB_33      0.0016886000
_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  0.0242
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22323
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.780
_diffrn_reflns_theta_min         3.707
_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  0.786
_exptl_absorpt_correction_T_min  0.465
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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       prism
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0247
_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^)+(0.0300P)^2^+0.6283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0623
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3989
_reflns_number_total             4059
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03991e2.cif
_cod_data_source_block           trans_anti-(BA)-3
_cod_database_code               1567647
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C21 H29 Br O4'
_shelx_estimated_absorpt_t_max   0.778
_shelx_estimated_absorpt_t_min   0.445
_reflns_odcompleteness_completeness 99.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C8(H8), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C17(H17A,H17B), C18(H18A,H18B)
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:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              19001
_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 1.809
_oxdiff_exptl_absorpt_empirical_full_min 0.515