Synthesis and photophysics of a 2,7-disubstituted donor-acceptor pyrene derivative: an example of the application of sequential ir-catalyzed C-h borylation and substitution chemistry.
Ji, Lei; Lorbach, Andreas; Edkins, Robert M.; Marder, Todd B.; The Journal of organic chemistry 80 (2015) 5658–5665; doi:10.1021/acs.joc.5b00618

data_4030973
_publ_section_title
;
 Synthesis and photophysics of a 2,7-disubstituted donor-acceptor pyrene
 derivative: an example of the application of sequential ir-catalyzed C-h
 borylation and substitution chemistry.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5658
_journal_page_last               5665
_journal_paper_doi               10.1021/acs.joc.5b00618
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C17 H9 N'
_chemical_formula_sum            'C17 H9 N'
_chemical_formula_weight         227.25
_chemical_name_systematic        2-Cyanopyrene
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
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_cell_length_b                   15.185(5)
_cell_length_c                   15.531(5)
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_cell_measurement_temperature    102
_cell_measurement_theta_max      26.79
_cell_measurement_theta_min      2.63
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_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      102
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_max       5
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_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9093
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.792
_diffrn_reflns_theta_min         2.950
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0548 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.9065.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.132
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_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.044
_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     163
_refine_ls_number_reflns         2287
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0540P)^2^+0.1574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1619
_reflns_number_total             2287
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00618_si_002.cif
_cod_data_source_block           Cmpd_2
_cod_depositor_comments
'Adding full bibliography for 4030972--4030974.cif.'
_cod_original_cell_volume        1081.2(7)
_cod_database_code               4030973
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C14(H14), C4(H4), C5(H5), C12(H12), C9(H9), C8(H8), C11(H11), C7(H7)
;
_shelx_res_checksum              63027
_shelx_hkl_checksum              19162
_olex2_submission_special_instructions 'No special instructions were received'