Isolation and Characterization of the Unexpected 1- n-Octyloxyperopyrene: A Solution-Processable p-Type Organic Semiconductor.
Martínez-Abadía, Marta; Antonicelli, Gabriella; Saeki, Akinori; Melle-Franco, Manuel; Mateo-Alonso, Aurelio; The Journal of organic chemistry 84 (2019) 3270–3274; doi:10.1021/acs.joc.8b03207

data_4033896
_publ_section_title
;
 Isolation and Characterization of the Unexpected 1- n-Octyloxyperopyrene:
 A Solution-Processable p-Type Organic Semiconductor.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3270
_journal_page_last               3274
_journal_paper_doi               10.1021/acs.joc.8b03207
_journal_volume                  84
_journal_year                    2019
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C34 H30 O1'
_chemical_formula_sum            'C34 H30 O'
_chemical_formula_weight         454.58
_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'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-02-02T12:41:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 92.920(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.2223(5)
_cell_length_b                   13.7606(7)
_cell_length_c                   41.901(3)
_cell_measurement_reflns_used    3725
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.463
_cell_measurement_theta_min      4.497
_cell_measurement_wavelength     1.54184
_cell_volume                     4734.7(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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      7.00  33.00   1.00    4.00    --  -41.08  38.00-150.00   26
  2  \w    -69.00  30.00   1.00    4.00    --  -41.08  57.00  90.00   99
  3  \w     33.00 116.00   1.00    4.00    --   41.08  38.00 -90.00   83
  4  \w   -151.00-111.00   1.00   16.00    --  -83.00-125.00-180.00   40
  5  \w     76.00 156.00   1.00   16.00    --  108.36 125.00-120.00   80
  6  \w     98.00 148.00   1.00   16.00    --  108.36  45.00-120.00   50
  7  \w     59.00  85.00   1.00   16.00    --  108.36 -94.00 120.00   26
  8  \w     62.00 117.00   1.00   16.00    --  108.36-125.00-150.00   55
  9  \w     37.00 108.00   1.00   16.00    --  108.36 -94.00-120.00   71
 10  \w     37.00  68.00   1.00   16.00    --  108.36 -30.00 150.00   31
 11  \w     49.00  77.00   1.00   16.00    --  108.36 -45.00-120.00   28
 12  \w     46.00  76.00   1.00   16.00    --  108.36 -45.00 -30.00   30
 13  \w     44.00  72.00   1.00   16.00    --  108.36 -45.00-150.00   28
 14  \w     38.00  69.00   1.00   16.00    --  108.36 -30.00 120.00   31
 15  \w     39.00  69.00   1.00   16.00    --  108.36 -30.00  90.00   30
 16  \w    -74.00 -15.00   1.00    4.00    --  -41.08  77.00-150.00   59
 17  \w    -46.00   3.00   1.00    4.00    --  -41.08  57.00 -90.00   49
 18  \w     50.00  97.00   1.00    4.00    --   41.08  38.00 -30.00   47
 19  \w   -120.00 -65.00   1.00   16.00    --  -83.00 -30.00 -30.00   55
 20  \w    -67.00 -41.00   1.00   16.00    --  -83.00  45.00-150.00   26
 21  \w     95.00 136.00   1.00   16.00    --  108.36  30.00  30.00   41
 22  \w     86.00 141.00   1.00   16.00    --  108.36 125.00  30.00   55
 23  \w     41.00  70.00   1.00   16.00    --  108.36 -45.00   0.00   29
 24  \w    108.00 155.00   1.00   16.00    --  108.36  61.00 -60.00   47
 25  \w     35.00  76.00   1.00   16.00    --  108.36 -45.00  30.00   41
 26  \w     78.00 105.00   1.00   16.00    --  108.36  61.00 -60.00   27
 27  \w    105.00 154.00   1.00   16.00    --  108.36  45.00-150.00   49
 28  \w     33.00  58.00   1.00   16.00    --  108.36 -77.00  90.00   25
 29  \w    106.00 132.00   1.00   16.00    --  108.36 -77.00  90.00   26
 30  \w     56.00  90.00   1.00   16.00    --  108.36 -94.00  60.00   34
 31  \w     46.00 109.00   1.00   16.00    --  108.36 -94.00 -30.00   63
 32  \w     34.00  73.00   1.00   16.00    --  108.36 -45.00 -60.00   39
;
_diffrn_measurement_device       'four-circle\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0137881
_diffrn_orient_matrix_UB_12      -0.1073925
_diffrn_orient_matrix_UB_13      -0.0102159
_diffrn_orient_matrix_UB_21      -0.0260146
_diffrn_orient_matrix_UB_22      -0.0292825
_diffrn_orient_matrix_UB_23      0.0348397
_diffrn_orient_matrix_UB_31      -0.1852872
_diffrn_orient_matrix_UB_32      0.0121754
_diffrn_orient_matrix_UB_33      -0.0060493
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_unetI/netI     0.106
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            38166
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.998
_diffrn_reflns_theta_min         3.381
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.995
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     633
_refine_ls_number_reflns         8951
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.1608
_refine_ls_R_factor_gt           0.1194
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3253
_refine_ls_wR_factor_ref         0.371
_reflns_number_gt                4969
_reflns_number_total             8951
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03207_si_002.cif
_cod_data_source_block           a20170128_adp28f1d
_cod_database_code               4033896