One-Pot Synthesis of Stable NIR Tetracene Diimides via Double Cross-Coupling
Wan Yue; Jing Gao; Yan Li; Wei Jiang; Simone Di Motta; Fabrizia Negri; Zhaohui Wang; Journal of the American Chemical Society 133 (2011) 18054–18057; doi:10.1021/ja207630a

data_4107087
_publ_section_title
;
 One-Pot Synthesis of Stable NIR Tetracene Diimides via Double
 Cross-Coupling
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18054
_journal_page_last               18057
_journal_paper_doi               10.1021/ja207630a
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C46 H44 F14 N2 O4'
_chemical_formula_sum            'C46 H44 F14 N2 O4'
_chemical_formula_weight         954.83
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.587(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.048(6)
_cell_length_b                   14.838(3)
_cell_length_c                   11.731(3)
_cell_measurement_reflns_used    8643
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.54
_cell_volume                     4612.2(18)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20242
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.9863
_exptl_absorpt_correction_T_min  0.9480
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.11
_platon_squeeze_details
;
;
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     603
_refine_ls_number_reflns         8712
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0571
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0864P)^2^+3.8750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1496
_reflns_number_gt                8214
_reflns_number_total             8712
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja207630a_si_001.cif
_cod_data_source_block           mx673
_cod_original_cell_volume        4611.9(18)
_cod_database_code               4107087