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_1567644
_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         'C14 H26 O3'
_chemical_formula_sum            'C14 H26 O3'
_chemical_formula_weight         242.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_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                 90.764(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8614(2)
_cell_length_b                   15.5412(7)
_cell_length_c                   14.8746(7)
_cell_measurement_reflns_used    6749
_cell_measurement_temperature    119.99(10)
_cell_measurement_theta_max      73.9720
_cell_measurement_theta_min      4.0830
_cell_volume                     1354.85(10)
_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 0.998
_diffrn_measured_fraction_theta_max 0.977
_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    -62.00 -26.00   0.50   15.00    --  -57.30 -15.00-120.00   72
  2  \w    -81.00 -55.00   0.50   15.00    --  -57.30   0.00 -90.00   52
  3  \w    -65.00 -38.00   0.50   15.00    --  -57.30 125.00-120.00   54
  4  \w    -84.00 -20.00   0.50   15.00    --  -57.30   0.00 -60.00  128
  5  \w    -78.00 -52.00   0.50   15.00    --  -57.30 -15.00   0.00   52
  6  \w    -97.00 -40.00   0.50   15.00    --  -57.30   0.00  30.00  114
  7  \w     22.00  53.00   0.50   15.00    --   60.47 -94.00 120.00   62
  8  \w     31.00  62.00   0.50   15.00    --   60.47 -94.00 -30.00   62
  9  \w     25.00  57.00   0.50   15.00    --   60.47 -94.00  60.00   64
 10  \w     21.00  66.00   0.50   15.00    --   60.47 -94.00-180.00   90
 11  \w     25.00  62.00   0.50   15.00    --   60.47 -94.00-120.00   74
 12  \w     40.00  83.00   0.50   15.00    --   75.00 -94.00 120.00   86
 13  \w     47.00  73.00   0.50   15.00    --   75.00  15.00-120.00   52
 14  \w     36.00  64.00   0.50   15.00    --   75.00 -94.00 150.00   56
 15  \w     43.00  69.00   0.50   15.00    --   75.00-127.00  70.00   52
 16  \w     79.00 105.00   0.50   15.00    --   75.00-127.00  70.00   52
 17  \w     92.00 118.00   0.50   15.00    --   75.00  15.00-120.00   52
 18  \w     44.00  87.00   0.50   15.00    --   77.04 -94.00 -60.00   86
 19  \w     38.00  66.00   0.50   15.00    --   77.04 -94.00-180.00   56
 20  \w     39.00  89.00   0.50   15.00    --   77.04   0.00 150.00  100
 21  \w     76.00 107.00   0.50   15.00    --   77.04-125.00 -90.00   62
 22  \w     38.00  63.00   0.50   15.00    --   77.04-125.00 -90.00   50
 23  \w     93.00 123.00   0.50   15.00    --   77.04  15.00  60.00   60
 24  \w     41.00  86.00   0.50   15.00    --   77.04 -94.00  30.00   90
 25  \w     45.00  84.00   0.50   15.00    --   77.04 -94.00-150.00   78
 26  \w     54.00 121.00   0.50   15.00    --   77.04  15.00 -30.00  134
 27  \w     54.00  81.00   0.50   15.00    --   77.04-125.00   0.00   54
 28  \w     41.00 112.00   0.50   15.00    --   77.04   0.00-120.00  142
 29  \w     36.00  76.00   0.50   15.00    --   77.04-125.00  90.00   80
 30  \w     56.00  97.00   0.50   15.00    --   77.04  15.00  30.00   82
 31  \w     41.00  82.00   0.50   15.00    --   77.04 -94.00 -30.00   82
 32  \w     42.00  67.00   0.50   15.00    --   77.04 -94.00 -90.00   50
 33  \w     36.00  71.00   0.50   15.00    --   81.25-112.00  97.01   70
 34  \w     36.00 108.00   0.50   15.00    --   81.25-116.00  32.13  144
 35  \w     72.00 110.00   0.50   15.00    --   81.25-124.00-172.77   76
 36  \w     97.00 125.00   0.50   15.00    --   81.25-167.00  -8.65   56
 37  \w     66.00  92.00   0.50   15.00    --   81.25-167.00  -8.65   52
 38  \w     77.00 114.00   0.50   15.00    --   81.25-128.00-129.64   74
 39  \w     46.00  75.00   0.50   15.00    --   81.25 -75.00-149.92   58
 40  \w     68.00 127.00   0.50   15.00    --   81.25  18.00 149.82  118
 41  \w     76.00 104.00   0.50   15.00    --   81.25-112.00  97.01   56
 42  \w     40.00  65.00   0.50   15.00    --   81.25-128.00-129.64   50
 43  \w     36.00  67.00   0.50   15.00    --   81.25-124.00-172.77   62
 44  \w     57.00 108.00   0.50   15.00    --   81.25-116.00 123.04  102
;
_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      0.0007402000
_diffrn_orient_matrix_UB_12      0.0320978000
_diffrn_orient_matrix_UB_13      0.0979478000
_diffrn_orient_matrix_UB_21      0.0134620000
_diffrn_orient_matrix_UB_22      -0.0936420000
_diffrn_orient_matrix_UB_23      0.0335311000
_diffrn_orient_matrix_UB_31      0.2626294000
_diffrn_orient_matrix_UB_32      0.0047758000
_diffrn_orient_matrix_UB_33      -0.0006227000
_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  0.0827
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18499
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.876
_diffrn_reflns_theta_min         4.114
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49864
_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    1.188
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.083
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2728
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0735
_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^)+(0.0770P)^2^+0.7245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1494
_refine_ls_wR_factor_ref         0.1561
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2373
_reflns_number_total             2728
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03991e2.cif
_cod_data_source_block           trans_anti-(AA)-5
_cod_database_code               1567644
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H26 O3'
_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, All O(H) groups
2. Restrained distances
 O5-H5
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C4(H4), C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B)
3.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C8(H8A,H8B,H8C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              660
_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 2.044
_oxdiff_exptl_absorpt_empirical_full_min 0.532