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_7061586
_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         'C23 H20 O'
_chemical_formula_sum            'C23 H20 O'
_chemical_formula_weight         312.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-25
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-04-25 deposited with the CCDC.	2022-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                87.212(6)
_cell_angle_beta                 84.983(5)
_cell_angle_gamma                89.862(6)
_cell_formula_units_Z            2
_cell_length_a                   5.7804(3)
_cell_length_b                   8.8933(7)
_cell_length_c                   16.3510(11)
_cell_measurement_reflns_used    2355
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.3240
_cell_measurement_theta_min      3.3080
_cell_volume                     836.34(10)
_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)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -79.00   32.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241    0.0000   90.0000 111

  2 omega  -80.00    4.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -77.0000  -60.0000 84

  3 omega  -90.00  -58.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  178.0000  -60.0000 32

  4 omega  -25.00   64.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  120.0000 89

  5 omega   -7.00   93.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000 -120.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0744056000
_diffrn_orient_matrix_UB_12      -0.0262706000
_diffrn_orient_matrix_UB_13      0.0345057000
_diffrn_orient_matrix_UB_21      0.0311825000
_diffrn_orient_matrix_UB_22      0.0627455000
_diffrn_orient_matrix_UB_23      0.0218843000
_diffrn_orient_matrix_UB_31      -0.0930843000
_diffrn_orient_matrix_UB_32      0.0418223000
_diffrn_orient_matrix_UB_33      -0.0152057000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7027
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         3.313
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94047
_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            colorless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       tables
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0705P)^2^+0.2764P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1470
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3205
_reflns_number_total             3839
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj01828d2.cif
_cod_data_source_block           zak2
_cod_depositor_comments
'Adding full bibliography for 7061586--7061588.cif.'
_cod_database_code               7061586
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'N2 O3 C15 H12 s1'
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C23(H23), C15(H15), C21(H21), C8(H8), C11(H11), C2(H2), C19(H19),
 C14(H14), C9(H9), C20(H20), C7(H7), C3(H3), C13(H13), C10(H10), C16(H16),
 C22(H22)
;
_shelx_res_checksum              86214
_olex2_submission_special_instructions 'No special instructions were received'