Functionalization of the "Bay Region" of Perylene in Reaction with 1-Arylalk-2-yn-1-ones Catalyzed by Trifluoromethanesulfonic Acid: One-Step Approach to 1-Acyl-2-alkylbenzo[ ghi]perylenes.
Głodek, Marta; Makal, Anna; Plażuk, Damian; The Journal of organic chemistry 83 (2018) 14165–14174; doi:10.1021/acs.joc.8b02280

data_4034858
_publ_section_title
;
 Functionalization of the &quot;Bay Region&quot; of Perylene in Reaction
 with 1-Arylalk-2-yn-1-ones Catalyzed by Trifluoromethanesulfonic Acid:
 One-Step Approach to 1-Acyl-2-alkylbenzo[ ghi]perylenes.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14165
_journal_page_last               14174
_journal_paper_doi               10.1021/acs.joc.8b02280
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C24 H14 O'
_chemical_formula_sum            'C24 H14 O'
_chemical_formula_weight         318.35
_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     direct
_audit_creation_date             2014-10-21
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.954(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7858(6)
_cell_length_b                   9.8955(5)
_cell_length_c                   11.8458(6)
_cell_measurement_reflns_used    4531
_cell_measurement_temperature    100.01(1)
_cell_measurement_theta_max      76.1210
_cell_measurement_theta_min      3.4250
_cell_volume                     1493.15(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega  -48.00   15.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -      -41.0313   38.0000 -150.0000 63

  2 omega  -50.00   19.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -      -41.0313   38.0000  -90.0000 69

  3 omega  -40.00   32.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -      -41.0313   38.0000  -30.0000 72

  4 omega -116.00   -7.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -      -41.0313  -19.0000  150.0000 109

  5 omega   54.00  117.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       41.0313   77.0000  -90.0000 63

  6 omega   18.00   91.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       41.0313   38.0000  -60.0000 73

  7 omega    9.00   68.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       41.0313   77.0000    0.0000 59

  8 omega    9.00   81.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       41.0313   77.0000 -180.0000 72

  9 omega    9.00   92.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       41.0313   77.0000   90.0000 83

 10 omega    8.00   41.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       41.0313   77.0000  -90.0000 33

 11 omega    2.00   44.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       41.0313  -99.0000   90.0000 42

 12 omega    6.00   79.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       41.0313  -99.0000   30.0000 73

 13 omega   13.00   76.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       41.0313   57.0000   60.0000 63

 14 omega   47.00   95.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       41.0313 -125.0000  -60.0000 48

 15 omega    5.00   31.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       41.0313   90.0000  -40.5261 26

 16 omega   23.00   69.00   1.0000    2.2500
omega____ theta____ kappa____ phi______ frames
    -       41.0313 -125.0000  150.0000 46

 17 omega   79.00  127.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -90.0000 48

 18 omega   78.00  116.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -180.0000 38

 19 omega   81.00  107.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   71.0000  -46.9604 26

 20 omega   48.00   75.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -180.0000 27

 21 omega  123.00  148.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -30.0000 25

 22 omega   40.00   97.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   60.0000 57

 23 omega   85.00  112.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000 -159.5329 27

 24 omega   79.00  107.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   30.0000 28

 25 omega  116.00  178.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   30.0000 62

 26 omega   83.00  176.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  120.0000 93

 27 omega   83.00  173.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   90.0000 90

 28 omega   47.00  115.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   60.0000 68

 29 omega   83.00  110.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -120.0000 27

 30 omega  135.00  162.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -90.0000 27

 31 omega   81.00  107.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   72.0000   57.2234 26

 32 omega   79.00  106.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   90.0000 27

 33 omega   83.00  109.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -90.0000 26

 34 omega  141.00  168.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   60.0000 27

 35 omega   79.00  105.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 26

 36 omega   79.00  105.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000    0.0000 26

 37 omega   38.00  109.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -150.0000 71

 38 omega   57.00  102.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   30.0000 45

 39 omega   82.00  178.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   67.0000 -174.1856 96

 40 omega  112.00  177.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000    0.0000 65

 41 omega   83.00  177.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -60.0000 94

 42 omega   80.00  140.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   60.0000 60

 43 omega   83.00  112.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   60.0000 29

 44 omega   45.00  108.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   90.0000 63

 45 omega   79.00  105.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  120.0000 26

 46 omega   79.00  106.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -30.0000 27

 47 omega   81.00  108.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -120.0000 27

 48 omega   86.00  113.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -120.0000 27

 49 omega   86.00  177.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -30.0000 91

 50 omega   83.00  118.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000    0.0000 35

 51 omega  128.00  155.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000    0.0000 27

 52 omega   53.00   80.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  120.0000 27

 53 omega  103.00  130.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  120.0000 27

 54 omega   83.00  123.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   62.0000    8.0982 40

 55 omega   83.00  110.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -150.0000 27

 56 omega   79.00  106.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -150.0000 27

 57 omega  119.00  171.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -150.0000 52

 58 omega  124.00  151.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   30.0000 27

 59 omega  133.00  160.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -180.0000 27

 60 omega   83.00  110.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -180.0000 27

 61 omega   37.00  116.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -30.0000 79

 62 omega   54.00   97.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 43

 63 omega   83.00  178.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  150.0000 95

 64 omega   37.00   90.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -90.0000 53

 65 omega   82.00  108.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   65.0000   98.0254 26

 66 omega   83.00  109.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   30.0000 26

 67 omega   82.00  107.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   70.0000  -56.1335 25

 68 omega   84.00  176.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   58.0000 -108.8153 92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0958384000
_diffrn_orient_matrix_UB_12      -0.0097079000
_diffrn_orient_matrix_UB_13      -0.0699995000
_diffrn_orient_matrix_UB_21      0.0478392000
_diffrn_orient_matrix_UB_22      0.1260005000
_diffrn_orient_matrix_UB_23      0.0609610000
_diffrn_orient_matrix_UB_31      0.0561240000
_diffrn_orient_matrix_UB_32      -0.0909201000
_diffrn_orient_matrix_UB_33      0.0918024000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28531
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.903
_diffrn_reflns_theta_min         3.470
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_recrystallization_method 'from anisole'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0940P)^2^+0.1456P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1517
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2268
_reflns_number_total             3138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02280_si_004.cif
_cod_data_source_block           exp_333
_cod_original_cell_volume        1493.16(13)
_cod_database_code               4034858
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C24 H14 O'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_olex2_exptl_crystal_mounting_method oil
_olex2_submission_special_instructions 'No special instructions were received'