Transformations of Conjugated Enynones in the Superacid CF3SO3H. Synthesis of Butadienyl Triflates, Indanones, and Indenes.
Saulnier, Steve; Golovanov, Alexander A.; Ivanov, Alexandr Yu; Boyarskaya, Irina A.; Vasilyev, Aleksander V.; The Journal of organic chemistry 81 (2016) 1967–1980; doi:10.1021/acs.joc.5b02785

data_4036565
_publ_section_title
;
 Transformations of Conjugated Enynones in the Superacid CF3SO3H.
 Synthesis of Butadienyl Triflates, Indanones, and Indenes.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1967
_journal_page_last               1980
_journal_paper_doi               10.1021/acs.joc.5b02785
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C19 H14 Br F3 O4 S'
_chemical_formula_sum            'C19 H14 Br F3 O4 S'
_chemical_formula_weight         475.27
_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     iterative
_audit_creation_date             2015-09-07
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_measurement_reflns_used    2962
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_cell_measurement_theta_max      76.0020
_cell_measurement_theta_min      5.2530
_cell_volume                     937.11(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega    8.00   35.00   1.0000    1.2400
omega____ theta____ kappa____ phi______ frames
    -      -40.1287   38.0000 -180.0000 27

  2 omega -128.00   38.00   1.0000    1.2400
omega____ theta____ kappa____ phi______ frames
    -      -40.1287    0.0000 -180.0000 166

  3 omega   16.00   82.00   1.0000    1.2400
omega____ theta____ kappa____ phi______ frames
    -       40.1287  -99.0000  -60.0000 66

  4 omega   70.00  115.00   1.0000    1.2400
omega____ theta____ kappa____ phi______ frames
    -       40.1287  178.0000 -150.0000 45

  5 omega   64.00  104.00   1.0000    1.2400
omega____ theta____ kappa____ phi______ frames
    -       40.1287  178.0000  120.0000 40

  6 omega   67.00  109.00   1.0000    1.2400
omega____ theta____ kappa____ phi______ frames
    -       40.1287 -178.0000  -60.0000 42

  7 omega   37.00   91.00   1.0000    4.9600
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  150.0000 54

  8 omega  116.00  174.00   1.0000    4.9600
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -180.0000 58

  9 omega   66.00  145.00   1.0000    4.9600
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -120.0000 79

 10 omega   54.00  157.00   1.0000    4.9600
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000    0.0000 103

 11 omega   82.00  115.00   1.0000    4.9600
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 33

 12 omega   36.00   90.00   1.0000    4.9600
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 54

 13 omega   77.00  114.00   1.0000    4.9600
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 37

 14 omega   45.00   70.00   1.0000    4.9600
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 25

 15 omega   59.00   99.00   1.0000    4.9600
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 40

 16 omega   30.00   91.00   1.0000    4.9600
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  120.0000 61

 17 omega   81.00  108.00   1.0000    4.9600
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 27

 18 omega   35.00   78.00   1.0000    4.9600
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 43

 19 omega  111.00  169.00   1.0000    4.9600
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  150.0000 58

 20 omega   91.00  178.00   1.0000    4.9600
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -120.0000 87

 21 omega   43.00   94.00   1.0000    4.9600
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -180.0000 51

 22 omega  109.00  141.00   1.0000    4.9600
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -180.0000 32
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0219825000
_diffrn_orient_matrix_UB_12      -0.1544482000
_diffrn_orient_matrix_UB_13      0.0421564000
_diffrn_orient_matrix_UB_21      -0.1274135000
_diffrn_orient_matrix_UB_22      0.0399703000
_diffrn_orient_matrix_UB_23      0.0757119000
_diffrn_orient_matrix_UB_31      -0.1301205000
_diffrn_orient_matrix_UB_32      -0.0892345000
_diffrn_orient_matrix_UB_33      -0.0815414000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6145
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.976
_diffrn_reflns_theta_min         3.414
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.524
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'brownish yellow'
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_description
;
;
_exptl_crystal_F_000             476
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_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3533
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0728P)^2^+0.0412P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3068
_reflns_number_total             3533
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02785_si_002.cif
_cod_data_source_block           103-129-2734_sau189b
_cod_original_cell_volume        937.11(9)
_cod_database_code               4036565
_chemical_oxdiff_formula         'Br S F3 O4 C19 H14'
_reflns_odcompleteness_completeness 99.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C12(H12), C13(H13), C14(H14),
 C16(H16), C18(H18)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              73007
_shelx_hkl_checksum              47810
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'