Aromatization of Benzannulated Perylene-3,9-diones: Unexpected Photophysical Properties and Reactivity.
Rao, M. Rajeswara; Johnson, Shea; Perepichka, Dmitrii F.; Organic letters 18 (2016) 3574–3577; doi:10.1021/acs.orglett.6b01559

data_1555616
_publ_section_title
;
 Aromatization of Benzannulated Perylene-3,9-diones: Unexpected
 Photophysical Properties and Reactivity.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3574
_journal_page_last               3577
_journal_paper_doi               10.1021/acs.orglett.6b01559
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C49 H25 F9'
_chemical_formula_sum            'C49 H25 F9'
_chemical_formula_weight         784.69
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-08-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7462(4)
_cell_length_b                   17.2319(7)
_cell_length_c                   23.8323(10)
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.444
_cell_measurement_theta_min      2.754
_cell_volume                     4002.5(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            62154
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         67.525
_diffrn_reflns_theta_min         2.753
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1162 before and 0.0828 after correction.
The Ratio of minimum to maximum transmission is 0.8024.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            purple
_exptl_crystal_colour_primary    purple
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.5(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         10752
_refine_ls_number_restraints     131
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0784P)^2^+0.6084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1454
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                8665
_reflns_number_total             10752
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01559_si_002.cif
_cod_data_source_block           pere57
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1555616
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.895
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C39-F4A \\sim C39-F4B \\sim C39-F5A \\sim C39-F5B \\sim C39-F6A \\sim C39-F6B
\\sim C39-F4C \\sim C39-F5C
 \\sim C39-F6C
 with sigma of 0.02
 F4A-F5A \\sim F4A-F6A \\sim F5A-F6A \\sim F4B-F5B \\sim F4B-F6B \\sim F5B-F6B
\\sim F4C-F5C \\sim F4C-F6C
 \\sim F5C-F6C
 with sigma of 0.02
 C49-F7A \\sim C49-F7B \\sim C49-F8A \\sim C49-F8B \\sim C49-F8A \\sim C49-F8B
\\sim C49-F7C \\sim C49-F8C
 \\sim C49-F9C
 with sigma of 0.02
 F7A-F8A \\sim F7A-F9A \\sim F8A-F9A \\sim F7B-F8B \\sim F7B-F9B \\sim F8B-F9B
\\sim F7C-F8C \\sim F7C-F9C
 \\sim F8C-F9C
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F4A) = Uanis(F4B) = Uanis(F5A) = Uanis(F5B) = Uanis(F6A) = Uanis(F6B) =
Uanis(F4C) = Uanis(F5C) = Uanis(F6C)
Uanis(F7A) = Uanis(F7B) = Uanis(F8A) = Uanis(F8B) = Uanis(F9A) = Uanis(F9B) =
Uanis(F7C) = Uanis(F8C) = Uanis(F9C)
4. Others
 1*[Sof(F7A)+Sof(F8A)+Sof(F9A)]+1*[Sof(F7B)+Sof(F8B)+Sof(F9B)]+1*[Sof(F7C)+
 Sof(F8C)+Sof(F9C)]=1 with esd of 0.00001
 1*[Sof(F4A)+Sof(F5A)+Sof(F6A)]+1*[Sof(F4B)+Sof(F5B)+Sof(F6B)]+1*[Sof(F4C)+
 Sof(F5C)+Sof(F6C)]=1 with esd of 0.00001
 Sof(F7A)=Sof(F8A)=Sof(F9A)=FVAR(1)
 Sof(F7B)=Sof(F8B)=Sof(F9B)=FVAR(2)
 Sof(F7C)=Sof(F8C)=Sof(F9C)=FVAR(3)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=FVAR(4)
 Sof(F4B)=Sof(F5B)=Sof(F6B)=FVAR(5)
 Sof(F4C)=Sof(F5C)=Sof(F6C)=FVAR(6)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C16(H16), C17(H17),
 C18(H18), C19(H19), C23(H23), C24(H24), C25(H25), C30(H30), C31(H31), C33(H33),
  C34(H34), C37(H37), C38(H38), C40(H40), C41(H41), C44(H44), C45(H45),
 C47(H47), C48(H48)
;
_olex2_submission_special_instructions 'No special instructions were received'