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_1553480
_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         258.34
_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             2015-07-06
_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                 94.193(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.7876(9)
_cell_length_b                   19.8876(14)
_cell_length_c                   12.1607(8)
_cell_measurement_reflns_used    3415
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.4690
_cell_measurement_theta_min      3.9690
_cell_volume                     2843.2(4)
_computing_cell_refinement
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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)
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_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)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_details
;
  1 omega  -65.00   33.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        8.4857  -38.0000    0.0000 98

  2 omega  -18.00   26.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        8.4857  -99.0000  -30.0000 44

  3 omega   -6.00   81.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        8.4857   19.0000    0.0000 87

  4 omega   -1.00   25.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        8.4857   38.0000 -150.0000 26

  5 omega  -10.00   85.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        8.4857   77.0000  120.0000 95
;
_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      -0.0576786000
_diffrn_orient_matrix_UB_12      0.0007031000
_diffrn_orient_matrix_UB_13      0.0129313000
_diffrn_orient_matrix_UB_21      0.0071710000
_diffrn_orient_matrix_UB_22      -0.0314896000
_diffrn_orient_matrix_UB_23      0.0270654000
_diffrn_orient_matrix_UB_31      0.0160696000
_diffrn_orient_matrix_UB_32      0.0167318000
_diffrn_orient_matrix_UB_33      0.0502370000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25498
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.757
_diffrn_reflns_theta_min         3.360
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54861
_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    1.207
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.037
_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     351
_refine_ls_number_reflns         6364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1574
_refine_ls_R_factor_gt           0.0679
_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^)+(0.0749P)^2^+0.5194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.2007
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3021
_reflns_number_total             6364
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00212a2.cif
_cod_data_source_block           po290f2
_cod_depositor_comments
;

2022-11-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C17 H22 O2)'
_cod_original_formula_sum        'C34 H44 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     516.69
_cod_database_code               1553480
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C24A) = Uanis(C24B)
3. Others
 Sof(H23C)=Sof(H23D)=Sof(H25C)=Sof(H25D)=Sof(C24B)=Sof(H24C)=Sof(H24D)=1-FVAR(1)
 Sof(H23A)=Sof(H23B)=Sof(C24A)=Sof(H24A)=Sof(H24B)=Sof(H25A)=Sof(H25B)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C4(H4), C21(H21)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C19(H19A,
 H19B), C20(H20A,H20B), C23(H23A,H23B), C23(H23C,H23D), C24A(H24A,H24B),
 C25(H25A,H25B), C25(H25C,H25D), C24B(H24C,H24D)
4.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C30(H30), C31(H31),
 C32(H32), C33(H33), C34(H34)
4.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C)
;
_olex2_submission_special_instructions 'No special instructions were received'