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_7061587
_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         'C25 H24 O'
_chemical_formula_sum            'C25 H24 O'
_chemical_formula_weight         340.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-02-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2022-02-18 deposited with the CCDC.	2022-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.212(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4843(7)
_cell_length_b                   5.6568(6)
_cell_length_c                   34.252(3)
_cell_measurement_reflns_used    3119
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.6970
_cell_measurement_theta_min      2.5590
_cell_volume                     1826.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.987
_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    -80.00 -42.00   0.50    5.06    --  -38.95 116.00 -53.00   76
  2  \w    -25.00   5.00   0.50    5.06    --  -38.95 116.00 -53.00   60
  3  \w    -88.00 -61.00   0.50    5.06    --  -38.95 165.00  93.00   54
  4  \w     54.00  90.00   0.50    5.06    --   38.95 165.00  93.00   72
  5  \w      5.00  30.00   0.50    5.06    --   38.95-116.00-142.00   50
  6  \w     45.00  71.00   0.50   10.00    --  100.00-116.00-142.00   52
  7  \w     79.00 136.00   0.50   10.00    --  100.00 116.00 -53.00  114
  8  \w     41.00 145.00   0.50   10.00    --  100.00-165.00  70.00  208
  9  \w     77.00 102.00   0.50   10.00    --  100.00 165.00  93.00   50
 10  \w     -9.00  25.00   0.50    5.06    --  -38.95  32.00  90.00   68
 11  \w    -55.00 -20.00   0.50    5.06    --  -38.95 -21.00-180.00   70
 12  \w   -109.00 -66.00   0.50    5.06    --  -38.95 -21.00-180.00   86
 13  \w    -15.00  24.00   0.50    5.06    --  -38.95  32.00 120.00   78
 14  \w    -72.00 -47.00   0.50    5.06    --  -38.95-165.00  70.00   50
 15  \w    -54.00 -13.00   0.50    5.06    --  -38.95 -77.00  60.00   82
 16  \w    -52.00 -15.00   0.50    5.06    --  -38.95  32.00  90.00   74
 17  \w   -104.00 -58.00   0.50    5.06    --  -38.95 -77.00  60.00   92
 18  \w    -13.00  22.00   0.50    5.06    --   38.95 -43.00 -60.00   70
 19  \w    -27.00  -1.00   0.50    5.06    --   38.95 -77.00-180.00   52
 20  \w     47.00  92.00   0.50    5.06    --   38.95-138.00  90.00   90
 21  \w     31.00  56.00   0.50    5.06    --   38.95 -77.00-180.00   50
 22  \w     22.00  49.00   0.50    5.06    --   38.95 -32.00 150.00   54
 23  \w    -25.00   1.00   0.50    5.06    --   38.95 -32.00 150.00   52
 24  \w     86.00 111.00   0.50   10.00    --  100.00-111.00   0.00   50
 25  \w     44.00  70.00   0.50   10.00    --  100.00-111.00   0.00   52
 26  \w    126.00 152.00   0.50   10.00    --  100.00  93.00 -90.00   52
 27  \w    120.00 156.00   0.50   10.00    --  100.00  45.00   0.00   72
 28  \w     81.00 145.00   0.50   10.00    --  100.00  93.00  60.00  128
 29  \w     43.00 114.00   0.50   10.00    --  100.00 -61.00-180.00  142
 30  \w     88.00 115.00   0.50   10.00    --  100.00 -37.00 150.00   54
 31  \w     90.00 139.00   0.50   10.00    --  100.00  53.00 -60.00   98
 32  \w     34.00  74.00   0.50   10.00    --  100.00 -37.00 150.00   80
 33  \w     73.00 115.00   0.50   10.00    --  100.00 -37.00-180.00   84
 34  \w    123.00 156.00   0.50   10.00    --  100.00  77.00   0.00   66
 35  \w     42.00  92.00   0.50   10.00    --  100.00-111.00  60.00  100
 36  \w     82.00 126.00   0.50   10.00    --  100.00 -77.00-150.00   88
 37  \w     65.00 111.00   0.50   10.00    --  100.00-111.00-120.00   92
 38  \w     81.00 107.00   0.50   10.00    --  100.00  93.00-150.00   52
 39  \w     82.00 130.00   0.50   10.00    --  100.00 -86.00-150.00   96
 40  \w    104.00 129.00   0.50   10.00    --  100.00  30.00-150.00   50
 41  \w     74.00 113.00   0.50   10.00    --  100.00  77.00   0.00   78
 42  \w     62.00  94.00   0.50   10.00    --  100.00 -93.00-180.00   64
 43  \w     75.00 154.00   0.50   10.00    --  100.00  77.00  30.00  158
;
_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      0.1278044000
_diffrn_orient_matrix_UB_12      0.0346939000
_diffrn_orient_matrix_UB_13      -0.0236479000
_diffrn_orient_matrix_UB_21      -0.0320956000
_diffrn_orient_matrix_UB_22      0.2662568000
_diffrn_orient_matrix_UB_23      -0.0031684000
_diffrn_orient_matrix_UB_31      0.0967191000
_diffrn_orient_matrix_UB_32      0.0427016000
_diffrn_orient_matrix_UB_33      0.0385104000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9481
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.374
_diffrn_reflns_theta_min         2.595
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.50a (Rigaku Oxford Diffraction, 2019)
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    1.238
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3436
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.1501
_refine_ls_R_factor_gt           0.1357
_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^)+(0.0708P)^2^+23.7981P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3563
_refine_ls_wR_factor_ref         0.3642
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2781
_reflns_number_total             3436
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj01828d2.cif
_cod_data_source_block           9827-12954_mok144(1)
_cod_depositor_comments
'Adding full bibliography for 7061586--7061588.cif.'
_cod_database_code               7061587
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'O C20'
_diffrn_oxdiff_ac3_digest_frames
;
01520a606ba4b885a96d88cc74f79e945f019736c67
;
_diffrn_oxdiff_ac3_digest_hkl
;
010975947a84ec0074c0850ae88aeb23171b98
;
_reflns_odcompleteness_completeness 95.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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:
 C8(H8), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C5(H5), C14(H14), C13(H13), C6(H6), C15(H15), C12(H12), C22(H22),
 C25(H25), C26(H26), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              70665
_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 3.740
_oxdiff_exptl_absorpt_empirical_full_min 0.681