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_1558418
_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         '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             2019-12-16
_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                90
_cell_angle_beta                 90.681(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.84981(12)
_cell_length_b                   15.5147(4)
_cell_length_c                   14.8525(3)
_cell_measurement_reflns_used    10639
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.5780
_cell_measurement_theta_min      4.0890
_cell_volume                     1347.89(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_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      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix-Arc
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.982
_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    -53.00 -27.00   0.50    2.00    --  -54.64 133.00 -97.00   52
  2  \w    -84.00 -36.00   0.50    2.00    --  -54.64 135.00  81.00   96
  3  \w     44.00  69.00   0.50    2.00    --   63.00-135.00  15.00   50
  4  \w     46.00  73.00   0.50    2.00    --   72.51-133.00-165.00   54
  5  \w     49.00  74.00   0.50    2.00    --   72.51-135.00  15.00   50
  6  \w     85.00 111.00   0.50    2.00    --   76.66-135.00  15.00   52
  7  \w     82.00 109.00   0.50    2.00    --   76.66-133.00-165.00   54
  8  \w    -98.00 -73.00   0.50    2.00    --  -54.64 -15.00   0.00   50
  9  \w    -57.00 -24.00   0.50    2.00    --  -54.64 -15.00   0.00   66
 10  \w    -98.00 -31.00   0.50    2.00    --  -54.64 -15.00 -90.00  134
 11  \w     29.00  70.00   0.50    2.00    --   63.00 -94.00-150.00   82
 12  \w     44.00  70.00   0.50    2.00    --   72.51  15.00 -30.00   52
 13  \w     51.00 101.00   0.50    2.00    --   72.51-125.00  30.00  100
 14  \w     44.00  69.00   0.50    2.00    --   72.51 -94.00 -90.00   50
 15  \w     34.00  76.00   0.50    2.00    --   76.66-125.00 -90.00   84
 16  \w     35.00 103.00   0.50    2.00    --   76.66-125.00  60.00  136
 17  \w     39.00  64.00   0.50    2.00    --   76.66 -94.00-150.00   50
 18  \w     39.00  64.00   0.50    2.00    --   76.66 -94.00 -30.00   50
 19  \w     79.00 105.00   0.50    2.00    --   76.66-125.00-180.00   52
 20  \w     39.00  68.00   0.50    2.00    --   76.66 -94.00 150.00   58
 21  \w     42.00  67.00   0.50    2.00    --   76.66 -94.00 120.00   50
 22  \w     46.00 121.00   0.50    2.00    --   76.66  15.00-120.00  150
 23  \w     41.00  97.00   0.50    2.00    --   76.66   0.00 150.00  112
 24  \w     66.00 104.00   0.50    2.00    --   76.66-125.00 -30.00   76
 25  \w     37.00  92.00   0.50    2.00    --   76.66-125.00  90.00  110
 26  \w     40.00  66.00   0.50    2.00    --   76.66 -94.00   0.00   52
 27  \w     79.00 122.00   0.50    2.00    --   76.66  15.00 -60.00   86
 28  \w     41.00 108.00   0.50    2.00    --   77.50-128.00-102.97  134
 29  \w     48.00  74.00   0.50    2.00    --   77.50   4.00-120.99   52
 30  \w     55.00  80.00   0.50    2.00    --   77.50  13.00  12.86   50
 31  \w     62.00 123.00   0.50    2.00    --   77.50  22.00   5.03  122
 32  \w     50.00  76.00   0.50    2.00    --   77.50   4.00  22.90   52
 33  \w     81.00 106.00   0.50    2.00    --   77.50-124.00 156.65   50
 34  \w     38.00  69.00   0.50    2.00    --   77.50-124.00 156.65   62
 35  \w     86.00 111.00   0.50    2.00    --   77.50  73.00-111.30   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1009949000
_diffrn_orient_matrix_UB_12      0.0656207000
_diffrn_orient_matrix_UB_13      0.0675512000
_diffrn_orient_matrix_UB_21      -0.0874766000
_diffrn_orient_matrix_UB_22      0.0745991000
_diffrn_orient_matrix_UB_23      -0.0596110000
_diffrn_orient_matrix_UB_31      -0.2267621000
_diffrn_orient_matrix_UB_32      0.0003015000
_diffrn_orient_matrix_UB_33      0.0514389000
_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  0.0193
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_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            14706
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.186
_diffrn_reflns_theta_min         4.121
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.194
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.939
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0325P)^2^+0.5007P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0812
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2499
_reflns_number_total             2702
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02551h2.cif
_cod_data_source_block           tr_tr_AA_33
_cod_original_cell_volume        1347.88(5)
_cod_database_code               1558418
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H26 O3'
_reflns_odcompleteness_completeness 97.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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.a Ternary CH refined with riding coordinates:
 C1(H1), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C10(H10A,H10B), C11(H11A,H11B)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C9(H9A,H9B,H9C), C15(H15A,H15B,H15C),
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              1579
_shelx_hkl_checksum              68617
_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 1.661
_oxdiff_exptl_absorpt_empirical_full_min 0.750