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_4036566
_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         'C18 H16 O3'
_chemical_formula_sum            'C18 H16 O3'
_chemical_formula_weight         280.31
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-19
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
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_cell_formula_units_Z            4
_cell_length_a                   17.2307(4)
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_cell_measurement_reflns_used    5235
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.7420
_cell_measurement_theta_min      6.0210
_cell_volume                     1372.60(6)
_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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;
  1 omega    0.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  120.0000 33

  2 omega  -67.00   34.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   57.0000  -30.0000 101

  3 omega -106.00  -23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000 -180.0000 83

  4 omega   82.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000  -90.0000 26

  5 omega   32.00  108.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 76

  6 omega   38.00   81.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 43

  7 omega   35.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 54

  8 omega   64.00  109.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000    0.0000 45

  9 omega   81.00  108.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  150.0000 27

 10 omega  125.00  151.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -150.0000 26

 11 omega   61.00   87.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   60.0000 26

 12 omega  117.00  145.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -30.0000 28

 13 omega  123.00  169.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   98.0000 -116.0000 46

 14 omega   64.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 35

 15 omega   39.00   80.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 41

 16 omega   77.00  139.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   30.0000 62

 17 omega   38.00   77.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 39

 18 omega  104.00  169.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -30.0000 65

 19 omega  100.00  136.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 36

 20 omega  103.00  159.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 56

 21 omega   39.00   65.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  150.0000 26

 22 omega   81.00  107.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  120.0000 26

 23 omega   68.00   94.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 26

 24 omega  125.00  150.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   60.0000 25

 25 omega   79.00  105.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 26

 26 omega  -25.00   36.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -150.0000 61

 27 omega -113.00  -31.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   60.0000 82

 28 omega   71.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000    0.0000 27

 29 omega   57.00  104.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -150.0000 47

 30 omega   62.00   90.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 28

 31 omega   38.00   64.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -150.0000 26

 32 omega  105.00  131.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 26

 33 omega  149.00  175.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 26

 34 omega  110.00  136.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 26

 35 omega   92.00  118.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -60.0000 26

 36 omega   87.00  135.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 48

 37 omega   33.00   82.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  120.0000 49

 38 omega   55.00   80.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  150.0000 25

 39 omega  123.00  166.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   60.0000 43

 40 omega   40.00   85.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 45

 41 omega   94.00  135.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 41

 42 omega   60.00   87.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 27

 43 omega   55.00   80.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_13      0.0386132000
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_diffrn_orient_matrix_UB_22      -0.0439280000
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_diffrn_orient_matrix_UB_33      -0.0933594000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0245
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_diffrn_reflns_number            13383
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_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
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_diffrn_source                   'SuperNova (Cu) X-ray Source'
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_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
;
;
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description
;
;
_exptl_crystal_F_000             592
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_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0376
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1304
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2441
_reflns_number_total             2869
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02785_si_004.cif
_cod_data_source_block           sau_159
_cod_database_code               4036566
_chemical_oxdiff_formula         'C10 H10 O3'
_reflns_odcompleteness_completeness 95.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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 Ternary CH refined with riding coordinates:
 C00D(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C006(H006), C007(H007), C008(H008), C009(H009), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L)
2.d Idealised Me refined as rotating group:
 C00H(H00F,H00G,H00H)
;
_shelx_res_checksum              42461
_shelx_hkl_checksum              65349
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'