A Tin(IV) Chloride Promoted Tandem C-O Bond Cleavage/Nazarov Cyclization/Nucleophilic Addition Reaction of 1,1-Disubstituted Allylic Ethers toward the Synthesis of Multisubstituted Indenes.
Yang, Chao; Xu, Zheng-Liang; Shao, Hui; Mou, Xue-Qing; Wang, Jie; Wang, Shao-Hua; Organic letters 17 (2015) 5288–5291; doi:10.1021/acs.orglett.5b02610

data_1555357
_publ_section_title
;
 A Tin(IV) Chloride Promoted Tandem C-O Bond Cleavage/Nazarov
 Cyclization/Nucleophilic Addition Reaction of 1,1-Disubstituted Allylic
 Ethers toward the Synthesis of Multisubstituted Indenes.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5288
_journal_page_last               5291
_journal_paper_doi               10.1021/acs.orglett.5b02610
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C21 H16 F2 O'
_chemical_formula_sum            'C21 H16 F2 O'
_chemical_formula_weight         322.34
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-22
_audit_creation_method
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Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
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_cell_angle_alpha                78.708(14)
_cell_angle_beta                 82.706(14)
_cell_angle_gamma                89.789(12)
_cell_formula_units_Z            4
_cell_length_a                   8.2834(12)
_cell_length_b                   10.8217(16)
_cell_length_c                   18.382(3)
_cell_measurement_reflns_used    1558
_cell_measurement_temperature    293.18(10)
_cell_measurement_theta_max      25.3830
_cell_measurement_theta_min      3.7570
_cell_volume                     1602.4(4)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.18(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega    3.00   30.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000   30.0000 18

  2 omega  -48.00   42.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000 -120.0000 60

  3 omega  -20.00   61.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000 -120.0000 54

  4 omega   -7.00   24.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000   30.0000 21

  5 omega  -47.00   41.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000    0.0000 59

  6 omega  -34.00   35.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000  120.0000 46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0181983000
_diffrn_orient_matrix_UB_12      0.0303728000
_diffrn_orient_matrix_UB_13      -0.0380302000
_diffrn_orient_matrix_UB_21      -0.0608103000
_diffrn_orient_matrix_UB_22      -0.0375095000
_diffrn_orient_matrix_UB_23      -0.0097132000
_diffrn_orient_matrix_UB_31      -0.0585400000
_diffrn_orient_matrix_UB_32      0.0462595000
_diffrn_orient_matrix_UB_33      0.0058015000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.1099
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11166
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.29
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         6297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1376
_refine_ls_R_factor_gt           0.0748
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1774
_refine_ls_wR_factor_ref         0.2409
_reflns_number_gt                3220
_reflns_number_total             6297
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02610_si_002.cif
_cod_data_source_block           yangchao0518_2
_cod_original_cell_volume        1602.5(4)
_cod_database_code               1555357
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C19(H19A,H19B), C31(H31A,H31B),
 C32(H32A,H32B), C33(H33A,H33B), C40(H40A,H40B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C14(H14), C15(H15), C17(H17), C18(H18), C24(H24),
 C25(H25), C27(H27), C35(H35), C36(H36), C38(H38), C39(H39)
2.c :
 C21(H21), C42(H42)
;
_olex2_date_sample_data_collection 2015-05-18
_olex2_submission_special_instructions 'No special instructions were received'