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_4030972
_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         'C20 H19 N'
_chemical_formula_sum            'C20 H19 N'
_chemical_formula_weight         273.36
_chemical_name_systematic        2-(N,N-Diethylamino)pyrene
_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_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     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
_cell_angle_beta                 98.459(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1555(9)
_cell_length_b                   14.7517(16)
_cell_length_c                   11.9062(13)
_cell_measurement_reflns_used    7192
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.76
_cell_volume                     1416.8(3)
_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      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0199
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14192
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.754
_diffrn_reflns_theta_min         3.545
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0390 before and 0.0344 after correction.
The Ratio of minimum to maximum transmission is 0.9517.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.504
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.394
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0531P)^2^+0.4734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2652
_reflns_number_total             3005
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00618_si_002.cif
_cod_data_source_block           Cmpd_1
_cod_depositor_comments
'Adding full bibliography for 4030972--4030974.cif.'
_cod_database_code               4030972
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C12(H12), C14(H14), C4(H4), C7(H7), C8(H8), C5(H5), C9(H9), C11(H11)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              73803
_shelx_hkl_checksum              22132
_olex2_submission_special_instructions 'No special instructions were received'