A dinaphtho[8,1,2-cde:2',1',8'-uva]pentacene derivative and analogues: synthesis, structures, photophysical and electrochemical properties.
Li, Xiao-Jun; Li, Meng; Lu, Hai-Yan; Chen, Chuan-Feng; Organic & biomolecular chemistry 13 (2015) 7628–7632; doi:10.1039/c5ob01008j

data_7154531
_publ_section_title
;
 A dinaphtho[8,1,2-cde:2',1',8'-uva]pentacene derivative and analogues:
 synthesis, structures, photophysical and electrochemical properties.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7628
_journal_page_last               7632
_journal_paper_doi               10.1039/c5ob01008j
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C46 H42 Br2 O2 Si2'
_chemical_formula_sum            'C46 H42 Br2 O2 Si2'
_chemical_formula_weight         842.79
_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_date             2014-12-03
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2015-04-07 deposited with the CCDC.
2015-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                72.399(15)
_cell_angle_beta                 76.618(15)
_cell_angle_gamma                71.646(12)
_cell_formula_units_Z            4
_cell_length_a                   11.917(3)
_cell_length_b                   15.959(4)
_cell_length_c                   25.657(5)
_cell_measurement_reflns_used    11310
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      1.6846
_cell_volume                     4364.2(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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0255
_diffrn_orient_matrix_UB_12      0.0809
_diffrn_orient_matrix_UB_13      0.0284
_diffrn_orient_matrix_UB_21      -0.0649
_diffrn_orient_matrix_UB_22      -0.0064
_diffrn_orient_matrix_UB_23      0.0197
_diffrn_orient_matrix_UB_31      0.0213
_diffrn_orient_matrix_UB_32      -0.0231
_diffrn_orient_matrix_UB_33      0.0270
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_unetI/netI     0.0803
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            50951
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         1.433
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    1.947
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       plate
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.100
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     953
_refine_ls_number_reflns         19925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0741
_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^)+(0.0731P)^2^+4.8278P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1773
_refine_ls_wR_factor_ref         0.1898
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15778
_reflns_number_total             19925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01008j2.cif
_cod_data_source_block           mx3431_sq
_cod_depositor_comments
'Adding full bibliography for 7154531--7154532.cif.'
_cod_original_cell_volume        4364.2(17)
_cod_database_code               7154531
_shelxl_version_number           2013-4
_diffrn_number_total             19928
_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:
 C26(H26A,H26B), C27(H27A,H27B), C43(H43A,H43B), C44(H44A,H44B), C26A(H26C,
 H26D), C27A(H27C,H27D), C43A(H43C,H43D), C44A(H44C,H44D)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C29(H29), C30(H30),
 C40(H40), C41(H41), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C7A(H7A),
 C10A(H10A), C29A(H29A), C30A(H30A), C40A(H40A), C41A(H41A)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C35(H35A,H35B,H35C), C46(H46A,
 H46B,H46C), C17A(H17D,H17E,H17F), C18A(H18D,H18E,H18F), C19A(H19D,H19E,H19F),
 C22A(H22D,H22E,H22F), C23A(H23D,H23E,H23F), C24A(H24D,H24E,H24F), C35A(H35D,
 H35E,H35F), C46A(H46D,H46E,H46F)
;
_shelx_res_checksum              1070
_shelx_fab_checksum              26458