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_4034859
_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         'C31 H20 O'
_chemical_formula_sum            'C31 H20 O'
_chemical_formula_weight         408.47
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-12-06
_audit_creation_method
;
Olex2 1.2
(compiled Aug 10 2017 17:44:14 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.497(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0272(2)
_cell_length_b                   15.6481(4)
_cell_length_c                   13.5191(4)
_cell_measurement_reflns_used    13269
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      36.5190
_cell_measurement_theta_min      2.1640
_cell_volume                     1999.60(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_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_environment      air
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0013
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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 -92.00 -21.00 1.00 9.00 -- 0.71 160.00 60.00 71 2 \w -77.00 43.00 1.00 9.00 -- 0.71 -57.00 90.00 120 3 \w -41.00 78.00 1.00 9.00 -- 0.71 57.00-120.00 119 4 \w -95.00 -49.00 1.00 9.00 -- -1.03-160.00 60.00 46 5 \w -95.00 -49.00 1.00 9.00 -- -1.03-160.00 30.00 46 6 \w -4.00 32.00 1.00 20.00 -- 48.84 90.00 93.72 36 7 \w 73.00 132.00 1.00 20.00 -- 48.84 125.00 120.00 59 8 \w -30.00 90.00 1.00 20.00 -- 48.84 -61.00 60.00 120 9 \w 73.00 132.00 1.00 20.00 -- 48.84 125.00 90.00 59 10 \w 73.00 132.00 1.00 20.00 -- 48.84 125.00 150.00 59 11 \w -42.00 140.00 1.00 20.00 -- 48.84 -15.00 30.00 182 12 \w 2.00 120.00 1.00 20.00 -- 48.84-125.00 -90.00 118 13 \w -29.00 4.00 1.00 20.00 -- -49.15 -91.00 135.71 33 14 \w -132.00 -73.00 1.00 20.00 -- -49.15-125.00 60.00 59 15 \w -120.00 -2.00 1.00 20.00 -- -49.15 125.00-120.00 118 16 \w -128.00 -8.00 1.00 20.00 -- -49.15 -61.00 -90.00 120 17 \w -132.00 -73.00 1.00 20.00 -- -49.15-125.00 120.00 59 18 \w -94.00 -49.00 1.00 9.00 -- 0.71-160.00-180.00 45 19 \w -41.00 78.00 1.00 9.00 -- 0.71 57.00 150.00 119 20 \w -20.00 56.00 1.00 9.00 -- -1.03 -99.00 120.00 76'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0258901000
_diffrn_orient_matrix_UB_12      0.0274405000
_diffrn_orient_matrix_UB_13      -0.0440051000
_diffrn_orient_matrix_UB_21      0.0058653000
_diffrn_orient_matrix_UB_22      -0.0336372000
_diffrn_orient_matrix_UB_23      -0.0334852000
_diffrn_orient_matrix_UB_31      -0.0701858000
_diffrn_orient_matrix_UB_32      -0.0129704000
_diffrn_orient_matrix_UB_33      -0.0063530000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            37225
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         2.059
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.480
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0775P)^2^+0.4607P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1435
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4825
_reflns_number_total             5830
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02280_si_002.cif
_cod_data_source_block           mgk40129_1
_cod_original_cell_volume        1999.60(9)
_cod_database_code               4034859
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C31 H20 O'
_chemical_oxdiff_usercomment     '295K, colourless needle'
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.23
_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:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C26(H26), C27(H27), C29(H29), C30(H30)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C31(H31A,H31B,H31C)
;
_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 1.329
_oxdiff_exptl_absorpt_empirical_full_min 0.852