Bisindeno-annulated pentacenes with exceptionally high photo-stability and ordered molecular packing: simple synthesis by a regio-selective Scholl reaction
Arun Naibi Lakshminarayana; Jingjing Chang; Jie Luo; Bin Zheng; Kuo-Wei Huang; Chunyan Chi; Chem.Commun. 51 (2015) 3604–; doi:10.1039/C4cc09812A

data_7116554
_publ_section_title
;
 Bisindeno-annulated pentacenes with exceptionally high photo-stability
 and ordered molecular packing: simple synthesis by a regio-selective
 Scholl reaction
;
_journal_name_full               Chem.Commun.
_journal_page_first              3604
_journal_paper_doi               10.1039/C4cc09812A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C59 H70 O5'
_chemical_formula_weight         859.15
_chemical_name_common            'tetrahexyloxy rubicenoid pentacene'
_chemical_name_systematic        'tetrahexyloxy bisindenofused  pentacene'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-11-20 deposited with the CCDC.
2015-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                107.779(5)
_cell_angle_beta                 94.984(5)
_cell_angle_gamma                91.886(5)
_cell_formula_units_Z            1
_cell_length_a                   4.6842(5)
_cell_length_b                   14.8758(15)
_cell_length_c                   17.8030(18)
_cell_measurement_reflns_used    7040
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.63
_cell_measurement_theta_min      2.62
_cell_volume                     1174.5(2)
_computing.cell_refinement       'APEX2 v2013.6--2 (Bruker AXS)'
_computing.data_collection       'APEX2 (Bruker AXS)'
_computing.data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing.molecular_graphics    'Bruker SHELXTL'
_computing.publication_material  'Bruker SHELXTL'
_computing.structure_refinement  'SHELXL--2013 (Sheldrick 2013)'
_computing.structure_solution    'SHELXS--97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14776
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.650
_diffrn_reflns_theta_max         66.583
_diffrn_reflns_theta_min         2.620
_diffrn_source                   'Sealed Microfocusing Source'
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_crystal_colour            'Deep Green'
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4108
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0562P)^2^+0.8269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1359
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3176
_reflns_number_total             4108
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc09812a2.cif
_cod_data_source_block           E182
_cod_database_code               7116554
_shelx_estimated_absorpt_t_min   0.743
_shelx_estimated_absorpt_t_max   0.983
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_shelxl_version_number           2013-4
_shelx_res_checksum              13451
_shelx_hkl_checksum              3585