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_1567643
_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                94.139(2)
_cell_angle_beta                 91.6023(17)
_cell_angle_gamma                101.2879(17)
_cell_formula_units_Z            2
_cell_length_a                   6.41587(11)
_cell_length_b                   12.0405(3)
_cell_length_c                   13.3039(3)
_cell_measurement_reflns_used    9687
_cell_measurement_temperature    119.99(10)
_cell_measurement_theta_max      73.1740
_cell_measurement_theta_min      3.3250
_cell_volume                     1004.29(4)
_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      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 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   -102.00 -27.00   0.50    0.50    --  -57.30 -15.00-150.00  150
  2  \w    -87.00 -36.00   0.50    0.50    --  -57.30   0.00-180.00  102
  3  \w    -96.00 -18.00   0.50    0.50    --  -57.30   0.00 -90.00  156
  4  \w     28.00  56.00   0.50    0.50    --   60.47  15.00  90.00   56
  5  \w     42.00  90.00   0.50    0.50    --   60.47-125.00  90.00   96
  6  \w     22.00  69.00   0.50    0.50    --   60.47 -94.00-120.00   94
  7  \w     22.00  47.00   0.50    0.50    --   60.47 -94.00-180.00   50
  8  \w     62.00 100.00   0.50    0.50    --   60.47  15.00  90.00   76
  9  \w     70.00  99.00   0.50    0.50    --   60.47  15.00-180.00   58
 10  \w     22.00  70.00   0.50    0.50    --   60.47 -94.00 120.00   96
 11  \w     26.00  69.00   0.50    0.50    --   60.47 -94.00 -60.00   86
 12  \w     44.00  71.00   0.50    0.50    --   75.00 -94.00 120.00   54
 13  \w     35.00  69.00   0.50    0.50    --   75.00 -94.00-180.00   68
 14  \w     41.00  67.00   0.50    0.50    --   75.00-125.00 -30.00   52
 15  \w     36.00  80.00   0.50    0.50    --   75.00 -94.00  30.00   88
 16  \w     35.00  60.00   0.50    0.50    --   75.00 -94.00 150.00   50
 17  \w     44.00  70.00   0.50    0.50    --   75.00 -94.00 -30.00   52
 18  \w     38.00  67.00   0.50    0.50    --   77.04 -94.00  60.00   58
 19  \w     45.00  97.00   0.50    0.50    --   77.04  15.00-150.00  104
 20  \w     38.00  86.00   0.50    0.50    --   77.04 -94.00-120.00   96
 21  \w     39.00  65.00   0.50    0.50    --   77.04-125.00  60.00   52
 22  \w     72.00  98.00   0.50    0.50    --   77.04-125.00 150.00   52
 23  \w     36.00  62.00   0.50    0.50    --   77.04-125.00 150.00   52
 24  \w     83.00 108.00   0.50    0.50    --   77.04-125.00-120.00   50
 25  \w     56.00  81.00   0.50    0.50    --   77.04-122.00 142.00   50
 26  \w     77.00 106.00   0.50    0.50    --   77.04-125.00  60.00   58
 27  \w     35.00  60.00   0.50    0.50    --   77.04-125.00 -60.00   50
 28  \w     37.00  62.00   0.50    0.50    --   77.04 -94.00 -30.00   50
 29  \w     58.00  86.00   0.50    0.50    --   77.04 -94.00 -60.00   56
 30  \w     40.00  87.00   0.50    0.50    --   77.04 -94.00 -90.00   94
 31  \w     38.00  79.00   0.50    0.50    --   77.04   0.00-150.00   82
 32  \w     38.00  64.00   0.50    0.50    --   77.04 -94.00 120.00   52
 33  \w     50.00 119.00   0.50    0.50    --   77.04  15.00  30.00  138
 34  \w     55.00  80.00   0.50    0.50    --   77.04 -94.00   0.00   50
 35  \w     76.00 102.00   0.50    0.50    --   77.04-150.00 -19.00   52
 36  \w     50.00 106.00   0.50    0.50    --   77.04-125.00 120.00  112
 37  \w     62.00  87.00   0.50    0.50    --   77.04 -94.00-180.00   50
 38  \w     84.00 117.00   0.50    0.50    --   77.04   0.00-120.00   66
 39  \w     48.00  74.00   0.50    0.50    --   77.04 -94.00-150.00   52
 40  \w     65.00 119.00   0.50    0.50    --   77.04  15.00 -90.00  108
 41  \w     47.00 123.00   0.50    0.50    --   77.04  15.00 120.00  152
 42  \w     38.00  63.00   0.50    0.50    --   81.25 -55.00 139.97   50
 43  \w     47.00  88.00   0.50    0.50    --   81.25-105.00 167.91   82
 44  \w     86.00 115.00   0.50    0.50    --   81.25-133.00  25.84   58
 45  \w     40.00  82.00   0.50    0.50    --   81.25-133.00  25.84   84
;
_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      -0.0369097000
_diffrn_orient_matrix_UB_12      -0.0188754000
_diffrn_orient_matrix_UB_13      -0.1154079000
_diffrn_orient_matrix_UB_21      0.0370821000
_diffrn_orient_matrix_UB_22      0.1294649000
_diffrn_orient_matrix_UB_23      -0.0071980000
_diffrn_orient_matrix_UB_31      0.2394309000
_diffrn_orient_matrix_UB_32      0.0036129000
_diffrn_orient_matrix_UB_33      -0.0115575000
_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  0.0303
_diffrn_reflns_av_unetI/netI     0.0301
_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       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14479
_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         74.508
_diffrn_reflns_theta_min         3.334
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.972
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.638
_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    1.407
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0477P)^2^+1.0210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3516
_reflns_number_total             3964
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03991e2.cif
_cod_data_source_block           trans_syn-(BA)-3
_cod_database_code               1567643
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C21 H29 Br O4'
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.459
_reflns_odcompleteness_completeness 99.62
_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              43893
_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 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.748