Pnictogen-bonding catalysis: brevetoxin-type polyether cyclizations
Gini, Andrea; Paraja, Miguel; Galmés, Bartomeu; Besnard, Celine; Poblador-Bahamonde, Amalia I.; Sakai, Naomi; Frontera, Antonio; Matile, Stefan; Chemical Science  (2020) –; doi:10.1039/D0SC02551H

data_1558421
_publ_section_title
;
 Pnictogen-bonding catalysis: brevetoxin-type polyether cyclizations
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02551H
_journal_year                    2020
_chemical_formula_moiety         'C18 H6 F9 Sb'
_chemical_formula_sum            'C18 H6 F9 Sb'
_chemical_formula_weight         514.98
_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             2020-02-24
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-04-26 deposited with the CCDC.	2020-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                102.271(2)
_cell_angle_beta                 90.684(2)
_cell_angle_gamma                100.761(2)
_cell_formula_units_Z            2
_cell_length_a                   4.65720(10)
_cell_length_b                   11.8323(3)
_cell_length_c                   15.3860(3)
_cell_measurement_reflns_used    14511
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6470
_cell_measurement_theta_min      2.8850
_cell_volume                     812.73(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.53a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.53a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.53a (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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix-Arc
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.947
_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    -15.00  10.00   0.50    1.50    --   -4.00 102.00-132.55   50
  2  \w      1.00  26.00   0.50    1.50    --    8.00  97.00 -91.76   50
  3  \w     21.00  46.00   0.50    1.50    --   12.00  71.00 -18.81   50
  4  \w     16.00  41.00   0.50    1.50    --   16.00  86.00  41.89   50
  5  \w     12.00  37.00   0.50    1.50    --   16.00  92.00 136.61   50
  6  \w     16.00  41.00   0.50    1.50    --   16.00  86.00  78.05   50
  7  \w     24.00  49.00   0.50    1.50    --   20.00  80.00   7.02   50
  8  \w     24.00  49.00   0.50    1.50    --   20.00  80.00 153.84   50
  9  \w     17.00  43.00   0.50    1.50    --   20.00  90.00-173.27   52
 10  \w    -59.00 -34.00   0.50    1.50    --  -24.00 -72.00  97.85   50
 11  \w    -39.00 -12.00   0.50    1.50    --  -28.00 120.00  -1.74   54
 12  \w     39.00  64.00   0.50    1.50    --   28.00  63.00 -92.96   50
 13  \w     38.00  63.00   0.50    1.50    --   28.00  67.00   7.52   50
 14  \w    -58.00 -33.00   0.50    1.50    --  -28.00 -78.00 -67.97   50
 15  \w     40.00  65.00   0.50    1.50    --   28.00  60.00 164.32   50
 16  \w     37.00  62.00   0.50    1.50    --   32.00  77.00 -43.73   50
 17  \w     36.00  61.00   0.50    1.50    --   32.00  79.00 156.86   50
 18  \w     36.00  61.00   0.50    1.50    --   32.00  80.00 -99.86   50
 19  \w     48.00  73.00   0.50    1.50    --   36.00  58.00-123.47   50
 20  \w     50.00  76.00   0.50    1.50    --   36.00  56.00  32.31   52
 21  \w     44.00  69.00   0.50    1.50    --   40.00  80.00 -61.11   50
 22  \w     48.00  73.00   0.50    1.50    --   40.00  72.00-176.01   50
 23  \w     57.00  82.00   0.50    1.50    --   44.00  58.00 -71.92   50
 24  \w     56.00  81.00   0.50    1.50    --   44.00  58.00   4.95   50
 25  \w     48.00  73.00   0.50    1.50    --   44.00  80.00 149.19   50
 26  \w     48.00  73.00   0.50    1.50    --   44.00  79.00 -50.10   50
 27  \w     60.00  85.00   0.50    1.50    --   48.00  59.00-111.56   50
 28  \w     58.00  83.00   0.50    1.50    --   48.00  70.00  72.37   50
 29  \w     52.00  77.00   0.50    1.50    --   48.00  80.00  48.93   50
 30  \w     60.00  85.00   0.50    1.50    --   48.00  57.00-119.90   50
 31  \w     60.00  85.00   0.50    1.50    --   48.00  60.00 -97.64   50
 32  \w     56.00  81.00   0.50    1.50    --   48.00  72.00  44.45   50
 33  \w     58.00  83.00   0.50    1.50    --   48.00  70.00  96.19   50
 34  \w     64.00  89.00   0.50    1.50    --   52.00  61.00 -15.98   50
 35  \w     63.00  88.00   0.50    1.50    --   52.00  63.00  91.42   50
 36  \w    -65.00 -16.00   0.50    1.50    --  -52.73 125.00-120.00   98
 37  \w     66.00  91.00   0.50    1.50    --   56.00  70.00 -39.92   50
 38  \w    -90.00 -64.00   0.50    1.50    --  -56.00 -72.00  10.17   52
 39  \w    -98.00 -73.00   0.50    1.50    --  -60.50 -66.00-121.30   50
 40  \w    -96.00 -71.00   0.50    1.50    --  -60.50 -68.00  25.20   50
 41  \f    269.00 353.00   0.50    1.50 -62.75 -60.50  20.00    --   168
 42  \w    -93.00 -68.00   0.50    1.50    --  -60.50 -75.00 -37.72   50
 43  \w    -99.00 -44.00   0.50    1.50    --  -60.50 148.00 -84.05  110
 44  \w    -90.00 -65.00   0.50    1.50    --  -60.50 -79.00-150.76   50
 45  \w   -100.00 -75.00   0.50    1.50    --  -60.50 -59.00  30.97   50
 46  \w    -97.00 -71.00   0.50    1.50    --  -60.50 -65.00 175.65   52
 47  \f     95.00 120.00   0.50    1.50 -78.31 -60.50 -60.00    --    50
 48  \f     25.00  57.00   0.50    1.50 -78.31 -60.50 -60.00    --    64
 49  \f    248.00 282.00   0.50    1.50 -78.31 -60.50 -60.00    --    68
 50  \f    310.00 343.00   0.50    1.50 -78.31 -60.50 -60.00    --    66
 51  \w    -94.00 -69.00   0.50    1.50    --  -60.50 -71.00   9.38   50
 52  \w    -90.00 -65.00   0.50    1.50    --  -60.50 -79.00  92.21   50
 53  \w    -96.00 -70.00   0.50    1.50    --  -60.50 -68.00-140.91   52
 54  \w    -99.00 -73.00   0.50    1.50    --  -60.50 -58.00 122.16   52
 55  \w     35.00  92.00   0.50    1.50    --   67.40-125.00 -30.00  114
 56  \w     38.00 102.00   0.50    1.50    --   67.40  15.00 -90.00  128
 57  \w     35.00  79.00   0.50    1.50    --   67.40-125.00 150.00   88
 58  \w     56.00  85.00   0.50    1.50    --   67.40-125.00  60.00   58
 59  \w     65.00  92.00   0.50    1.50    --   67.40-125.00 -90.00   54
 60  \w     37.00  63.00   0.50    1.50    --   67.40-125.00 -90.00   52
 61  \w     80.00 107.00   0.50    1.50    --   67.40  15.00 150.00   54
 62  \w     41.00  76.00   0.50    1.50    --   67.40  15.00 150.00   70
 63  \w     58.00  84.00   0.50    1.50    --   67.40-125.00 -60.00   52
 64  \w     40.00  91.00   0.50    1.50    --   67.40-125.00-150.00  102
 65  \w     75.00 101.00   0.50    1.50    --   68.00  75.00  96.59   52
 66  \w     75.00 101.00   0.50    1.50    --   68.00  76.00 162.89   52
 67  \w     75.00 100.00   0.50    1.50    --   68.00  75.00 -58.32   50
 68  \w     75.00 102.00   0.50    1.50    --   68.00  74.00   9.51   54
 69  \w     35.00  63.00   0.50    1.50    --   69.81-125.00  90.00   56
 70  \w     41.00  94.00   0.50    1.50    --   69.81   0.00   0.00  106
 71  \w     35.00  78.00   0.50    1.50    --   69.81   0.00 240.00   86
 72  \w     35.00  93.00   0.50    1.50    --   69.81   0.00  60.00  116
 73  \w     71.00  96.00   0.50    1.50    --   69.81-125.00  30.00   50
 74  \w     36.00  69.00   0.50    1.50    --   69.81-125.00   0.00   66
 75  \w     42.00  96.00   0.50    1.50    --   69.81   0.00 300.00  108
 76  \w     71.00  96.00   0.50    1.50    --   69.81-125.00  90.00   50
 77  \f    186.00 217.00   0.50    1.50  91.14  73.33  60.00    --    62
 78  \f    125.00 163.00   0.50    1.50  91.14  73.33  60.00    --    76
 79  \f    333.00 360.00   0.50    1.50  91.14  73.33  60.00    --    54
 80  \f    247.00 300.00   0.50    1.50  91.14  73.33  60.00    --   106
 81  \f    164.00 239.00   0.50    1.50  54.95  73.33   0.00    --   150
 82  \f    123.00 160.00   0.50    1.50  54.95  73.33   0.00    --    74
 83  \w     37.00  95.00   0.50    1.50    --   75.25-116.00-137.48  116
 84  \f     93.00 120.00   0.50    1.50  56.87  75.25   0.00    --    54
 85  \f      2.00  84.00   0.50    1.50  56.87  75.25   0.00    --   164
 86  \f     34.00  84.00   0.50    1.50  93.06  75.25  60.00    --   100
 87  \w     39.00  90.00   0.50    1.50    --   75.25-106.00 102.47  102
 88  \w     36.00  98.00   0.50    1.50    --   75.25-118.00 163.42  124
 89  \f    325.00 353.00   0.50    1.50  77.50  75.25 -20.00    --    56
 90  \f    242.00 293.00   0.50    1.50  77.50  75.25 -20.00    --   102
 91  \w     38.00  89.00   0.50    1.50    --   75.25-105.00 -91.23  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0391250000
_diffrn_orient_matrix_UB_12      0.0310470000
_diffrn_orient_matrix_UB_13      0.1010263000
_diffrn_orient_matrix_UB_21      -0.0328463000
_diffrn_orient_matrix_UB_22      0.1251716000
_diffrn_orient_matrix_UB_23      -0.0064347000
_diffrn_orient_matrix_UB_31      -0.3333120000
_diffrn_orient_matrix_UB_32      -0.0425937000
_diffrn_orient_matrix_UB_33      -0.0168076000
_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  0.0525
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19583
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.074
_diffrn_reflns_theta_min         2.943
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    14.421
_exptl_absorpt_correction_T_max  0.825
_exptl_absorpt_correction_T_min  0.155
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.53a (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    2.104
_exptl_crystal_description       needle
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.536
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.741
_refine_diff_density_min         -1.221
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0308
_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^)+(0.0580P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0857
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2959
_reflns_number_total             3122
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02551h2.cif
_cod_data_source_block           agn02_09
_cod_database_code               1558421
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'Sb C18 H6 F9'
_reflns_odcompleteness_completeness 98.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C9(H9), C12(H12), C15(H15), C18(H18)
;
_shelx_res_checksum              71556
_shelx_hkl_checksum              16372
_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 1.666
_oxdiff_exptl_absorpt_empirical_full_min 0.380