Bismuth(iii) triflate-catalysed tandem cyclisations towards complex polycyclic ethers
Ondet, Pierrick; Lempenauer, Luisa; Duñach, Elisabet; Lemière, Gilles; Organic Chemistry Frontiers 3 (2016) 999–; doi:10.1039/C6QO00212A

data_1553481
_publ_section_title
;
 Bismuth(iii) triflate-catalysed tandem cyclisations towards complex
 polycyclic ethers
;
_journal_issue                   8
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              999
_journal_paper_doi               10.1039/C6QO00212A
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C17 H22 O2'
_chemical_formula_sum            'C17 H22 O2'
_chemical_formula_weight         258.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-03-26
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-02-10 deposited with the CCDC.
2016-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.315(5)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   19.1606(11)
_cell_length_b                   13.3348(5)
_cell_length_c                   23.8068(11)
_cell_measurement_reflns_used    5698
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.5740
_cell_measurement_theta_min      3.8960
_cell_volume                     5774.6(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
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_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
  1 omega  -67.00  -16.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -53.2951  -57.0000  -90.0000 51

  2 omega  -75.00   18.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  -60.0000 93

  3 omega   23.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       53.2951 -125.0000   60.0000 90

  4 omega   29.00   64.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5902  -25.0000  -90.0000 35

  5 omega   64.00  175.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5902   50.0000  -60.0000 111

  6 omega   99.00  145.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       53.2951  125.0000 -150.0000 46

  7 omega  114.00  141.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5902  178.0000 -180.0000 27

  8 omega   66.00  104.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5902  178.0000 -180.0000 38

  9 omega   99.00  136.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       53.2951  119.0000    4.0000 37

 10 omega   99.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5902  119.0000    4.0000 32

 11 omega   64.00  163.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5902   50.0000   60.0000 99

 12 omega   72.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -150.0000 27

 13 omega -140.00 -105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -53.2951  -99.0000   60.0000 35

 14 omega -149.00  -79.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -53.2951  -99.0000    0.0000 70

 15 omega -142.00 -117.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -53.2951  -57.0000  -90.0000 25

 16 omega   32.00  105.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5902 -111.0000  150.0000 73

 17 omega   27.00  104.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5902  -50.0000  150.0000 77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0449791000
_diffrn_orient_matrix_UB_12      0.0636964000
_diffrn_orient_matrix_UB_13      -0.0529821000
_diffrn_orient_matrix_UB_21      -0.0290100000
_diffrn_orient_matrix_UB_22      0.0641146000
_diffrn_orient_matrix_UB_23      0.0417757000
_diffrn_orient_matrix_UB_31      0.0656627000
_diffrn_orient_matrix_UB_32      0.0718647000
_diffrn_orient_matrix_UB_33      0.0097534000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20535
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.885
_diffrn_reflns_theta_min         3.849
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.189
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     689
_refine_ls_number_reflns         10461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0546P)^2^+0.8995P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1310
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7150
_reflns_number_total             10461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00212a2.cif
_cod_data_source_block           po280f1
_cod_depositor_comments
;

2022-05-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '4(C17 H22 O2)'
_cod_original_formula_sum        'C68 H88 O8'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1033.38
_cod_database_code               1553481
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B),
 C10(H10A,H10B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B),
  C40(H40A,H40B), C42(H42A,H42B), C43(H43A,H43B), C19(H19A,H19B), C20(H20A,
 H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C26(H26A,H26B),
 C27(H27A,H27B), C53(H53A,H53B), C54(H54A,H54B), C55(H55A,H55B), C56(H56A,H56B),
  C57(H57A,H57B), C59(H59A,H59B), C60(H60A,H60B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C46(H46), C47(H47),
 C48(H48), C49(H49), C50(H50), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33),
  C63(H63), C64(H64), C65(H65), C66(H66), C67(H67)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C51(H51A,H51B,H51C), C34(H34A,H34B,H34C), C68(H68A,H68B,
 H68C)
;
_olex2_submission_special_instructions 'No special instructions were received'