A controlled tandem transformation of conjugated enynones with arenes under superelectrophilic activation leading to aryl-substituted dienones and indenes
Saulnier, Steve; Golovanov, Alexander; Vasilyev, Aleksander; RSC Adv.  (2016) –; doi:10.1039/C6RA21965A

data_7226935
_publ_section_title
;
 A controlled tandem transformation of conjugated enynones with arenes
 under superelectrophilic activation leading to aryl-substituted dienones
 and indenes
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA21965A
_journal_year                    2016
_chemical_formula_moiety         'C27 H26 O'
_chemical_formula_sum            'C27 H26 O'
_chemical_formula_weight         366.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-08-03 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                106.357(8)
_cell_angle_beta                 108.462(8)
_cell_angle_gamma                106.315(8)
_cell_formula_units_Z            2
_cell_length_a                   10.0460(9)
_cell_length_b                   10.9526(10)
_cell_length_c                   11.2956(10)
_cell_measurement_reflns_used    2371
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.6660
_cell_measurement_theta_min      3.2800
_cell_volume                     1033.4(2)
_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
;
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)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -18.00   65.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  -60.0000 83

  2 omega   61.00   92.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -178.0000  120.0000 31

  3 omega    5.00   91.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000  120.0000 86

  4 omega    9.00   60.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000 -150.0000 51

  5 omega   37.00   63.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000   60.0000 26

  6 omega  -50.00   96.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616    0.0000  -60.0000 146
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0434677000
_diffrn_orient_matrix_UB_12      0.0666844000
_diffrn_orient_matrix_UB_13      0.0549372000
_diffrn_orient_matrix_UB_21      -0.0283975000
_diffrn_orient_matrix_UB_22      -0.0256542000
_diffrn_orient_matrix_UB_23      0.0421329000
_diffrn_orient_matrix_UB_31      0.0627904000
_diffrn_orient_matrix_UB_32      -0.0187835000
_diffrn_orient_matrix_UB_33      0.0214456000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8848
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         3.111
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92824
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0448P)^2^+0.3707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1223
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3618
_reflns_number_total             4736
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra21965a2.cif
_cod_data_source_block           103-129-4361_sau320
_cod_original_cell_volume        1033.42(18)
_cod_database_code               7226935
_chemical_oxdiff_formula         'C27 O'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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:
 C3(H3), C7(H7), C9(H9), C10(H10), C11(H11), C13(H13), C16(H16), C17(H17),
 C18(H18), C20(H20), C22(H22), C24(H24), C26(H26), C27(H27)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C15(H15A,H15B,H15C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'