Reactions of linear conjugated dienone structures with arenes under superelectrophilic activation conditions. An experimental and theoretical study of intermediate multicentered electrophilic species
Kochurin, Matvei A.; Ismagilova, Alina R.; Zakusilo, Dmitriy N.; Khoroshilova, Olesya V.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.; New Journal of Chemistry 46 (2022) 12041–12053; doi:10.1039/D2NJ01828D

data_7061588
_publ_section_title
;
 Reactions of linear conjugated dienone structures with arenes under
 superelectrophilic activation conditions. An experimental and theoretical
 study of intermediate multicentered electrophilic species
;
_journal_issue                   25
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12041
_journal_page_last               12053
_journal_paper_doi               10.1039/D2NJ01828D
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C19 H18 O'
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33
_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     dual
_audit_creation_date             2018-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2022-02-18 deposited with the CCDC.	2022-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.026(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8475(4)
_cell_length_b                   16.8287(7)
_cell_length_c                   11.1852(5)
_cell_measurement_reflns_used    4220
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.7380
_cell_measurement_theta_min      2.6050
_cell_volume                     1419.75(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -46.00 -19.00   0.50    0.31    --  -41.35  64.00  67.00   54
  2  \w    -58.00 -23.00   0.50    0.31    --  -41.35 -64.00 -68.00   70
  3  \w   -104.00 -61.00   0.50    0.31    --  -41.35 -64.00 -68.00   86
  4  \w     38.00  88.00   0.50    1.26    --  101.00 -64.00 -68.00  100
  5  \w    123.00 150.00   0.50    1.26    --  101.00  64.00  67.00   54
  6  \w     85.00 119.00   0.50    1.26    --  101.00  64.00  67.00   68
  7  \w    -90.00 -23.00   0.50    0.31    --  -41.35 -65.00  90.00  134
  8  \w    -48.00  22.00   0.50    0.31    --  -41.35  65.00-120.00  140
  9  \w     75.00 104.00   0.50    0.31    --   41.35  43.00-150.00   58
 10  \w    -17.00  58.00   0.50    0.31    --   41.35 -54.00 -30.00  150
 11  \w     66.00 108.00   0.50    0.31    --   41.35  21.00  30.00   84
 12  \w    -11.00  14.00   0.50    0.31    --   41.35 -64.00 -68.00   50
 13  \w     29.00  69.00   0.50    0.31    --   41.35  43.00-150.00   80
 14  \w     51.00  86.00   0.50    0.31    --   41.35  64.00  67.00   70
 15  \w    -12.00  18.00   0.50    0.31    --   41.35 -32.00 120.00   60
 16  \w     32.00  57.00   0.50    0.31    --   41.35  21.00  30.00   50
 17  \w     88.00 157.00   0.50    1.26    --  101.00  17.00 150.00  138
 18  \w    108.00 135.00   0.50    1.26    --  101.00  33.00 -90.00   54
 19  \w     95.00 156.00   0.50    1.26    --  101.00  25.00   0.00  122
 20  \w    102.00 149.00   0.50    1.26    --  101.00  33.00  60.00   94
 21  \w     53.00  83.00   0.50    1.26    --  101.00 -59.00 -30.00   60
 22  \w     40.00 114.00   0.50    1.26    --  101.00 -42.00 120.00  148
 23  \w     50.00  92.00   0.50    1.26    --  101.00 -25.00  60.00   84
 24  \w     76.00 111.00   0.50    1.26    --  101.00 -42.00 -60.00   70
 25  \w     92.00 120.00   0.50    1.26    --  101.00  17.00-150.00   56
 26  \w     38.00  69.00   0.50    1.26    --  101.00 -42.00 -60.00   62
 27  \w    123.00 150.00   0.50    1.26    --  101.00  17.00-150.00   54
 28  \w     49.00  85.00   0.50    1.26    --  101.00 -25.00-120.00   72
 29  \w     48.00  87.00   0.50    1.26    --  101.00 -33.00-150.00   78
 30  \w     86.00 111.00   0.50    1.26    --  101.00 -59.00 -30.00   50
 31  \w     53.00 113.00   0.50    1.26    --  101.00 -17.00 120.00  120
 32  \w     87.00 112.00   0.50    1.26    --  101.00  59.00-180.00   50
 33  \w     88.00 151.00   0.50    1.26    --  101.00  42.00  30.00  126
 34  \w     -3.00  22.00   0.50    0.31    --  -41.35  64.00  67.00   50
 35  \w    -93.00 -43.00   0.50    0.31    --  -41.35 -21.00 -30.00  100
 36  \w   -103.00 -78.00   0.50    0.31    --  -41.35 -43.00 150.00   50
 37  \w     24.00  51.00   0.50    0.31    --   41.35  54.00 -60.00   54
 38  \w     30.00  66.00   0.50    0.31    --   41.35  65.00-180.00   72
 39  \w     42.00  84.00   0.50    0.31    --   41.35  32.00  90.00   84
 40  \w     77.00 104.00   0.50    0.31    --   41.35  54.00 -60.00   54
 41  \w     40.00  66.00   0.50    0.31    --   41.35  43.00-180.00   52
 42  \w     79.00 104.00   0.50    0.31    --   41.35  43.00-180.00   50
 43  \w     69.00 104.00   0.50    0.31    --   41.35  65.00-180.00   70
 44  \w     77.00 116.00   0.50    1.26    --  101.00  77.00-180.00   78
 45  \w    127.00 152.00   0.50    1.26    --  101.00  59.00 150.00   50
 46  \w     77.00 104.00   0.50    1.26    --  101.00  77.00 150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1024394000
_diffrn_orient_matrix_UB_12      -0.0678716000
_diffrn_orient_matrix_UB_13      0.0415762000
_diffrn_orient_matrix_UB_21      0.1352814000
_diffrn_orient_matrix_UB_22      0.0002728000
_diffrn_orient_matrix_UB_23      0.1293274000
_diffrn_orient_matrix_UB_31      -0.1137013000
_diffrn_orient_matrix_UB_32      0.0613876000
_diffrn_orient_matrix_UB_33      0.0456015000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9098
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.086
_diffrn_reflns_theta_min         4.881
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0684
_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^)+(0.0955P)^2^+0.9766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1848
_refine_ls_wR_factor_ref         0.2027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2280
_reflns_number_total             2769
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj01828d2.cif
_cod_data_source_block           on2562-72
_cod_depositor_comments
'Adding full bibliography for 7061586--7061588.cif.'
_cod_database_code               7061588
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C25
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.825
_reflns_odcompleteness_completeness 99.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.55
_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:
 C4(H4), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C9(H9), C12(H12), C16(H16), C11(H11), C10(H10)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              831
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.942
_oxdiff_exptl_absorpt_empirical_full_min 0.718