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_4036567
_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         'C17 H13 Cl O2'
_chemical_formula_sum            'C17 H13 Cl O2'
_chemical_formula_weight         284.72
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-08-19
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_measurement_temperature    100.01(10)
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_computing_cell_refinement
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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)
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_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
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
  1 omega  -50.00   29.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -90.0000 79

  2 omega -116.00  -43.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000  -90.0000 73

  3 omega  -41.00   11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   30.0000 -146.0000 52

  4 omega   95.00  125.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -30.0000 30

  5 omega   55.00   81.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000 -120.0000 26

  6 omega   74.00  105.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 31

  7 omega   41.00   67.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 26

  8 omega   53.00   79.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 26

  9 omega   36.00   61.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 25

 10 omega  151.00  177.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -120.0000 26

 11 omega  106.00  146.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -90.0000 40

 12 omega   58.00   89.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 31

 13 omega   90.00  130.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 40

 14 omega  151.00  177.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  120.0000 26

 15 omega   37.00   91.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 54

 16 omega  103.00  149.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -120.0000 46

 17 omega  103.00  137.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   60.0000 34

 18 omega   63.00   89.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   60.0000 26

 19 omega   44.00   76.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 32

 20 omega   49.00  112.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 63

 21 omega   41.00   67.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   30.0000 26

 22 omega   80.00  128.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 48

 23 omega   33.00   58.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000  150.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0310848000
_diffrn_orient_matrix_UB_12      0.0566681000
_diffrn_orient_matrix_UB_13      -0.1143225000
_diffrn_orient_matrix_UB_21      -0.1128375000
_diffrn_orient_matrix_UB_22      -0.0598977000
_diffrn_orient_matrix_UB_23      -0.0303585000
_diffrn_orient_matrix_UB_31      -0.0257771000
_diffrn_orient_matrix_UB_32      0.1929344000
_diffrn_orient_matrix_UB_33      0.0240233000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6452
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.495
_diffrn_reflns_theta_min         6.237
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.501
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description
;
;
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0569P)^2^+0.2259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1017
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2205
_reflns_number_total             2586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02785_si_003.cif
_cod_data_source_block           sau_157
_cod_original_cell_volume        1341.28(16)
_cod_database_code               4036567
_chemical_oxdiff_formula         'C10 H10 Cl O2'
_reflns_odcompleteness_completeness 91.15
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C9(H9), C12(H12), C14(H14), C15(H15), C16(H16)
;
_shelx_res_checksum              74532
_shelx_hkl_checksum              6733
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'