Donor- and acceptor-functionalized dibenzo[a,e]pentalenes: modulation of the electronic band gap
Wilbuer, J.; Grenz, D. C.; Schnakenburg, G.; Esser, B.; Organic Chemistry Frontiers 4 (2017) 658–; doi:10.1039/C6QO00487C

data_1553552
_publ_section_title
;
 Donor- and acceptor-functionalized dibenzo[a,e]pentalenes: modulation of
 the electronic band gap
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              658
_journal_paper_doi               10.1039/C6QO00487C
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         '2(C25 H19)'
_chemical_formula_sum            'C50 H38'
_chemical_formula_weight         638.80
_chemical_name_systematic        jm245.3b
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.21 svn.r3230 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-07-26 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                114.377(4)
_cell_angle_beta                 91.316(5)
_cell_angle_gamma                95.604(4)
_cell_formula_units_Z            2
_cell_length_a                   10.8252(8)
_cell_length_b                   13.5794(10)
_cell_length_c                   14.2122(10)
_cell_measurement_reflns_used    9181
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.18
_cell_measurement_theta_min      3.42
_cell_volume                     1889.2(2)
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon100 detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       'fine slicing \w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1028
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35349
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.700
_diffrn_reflns_theta_min         3.422
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.478
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4290
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1615 before and 0.1109 after correction.
The Ratio of minimum to maximum transmission is 0.5695.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear reddish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_description       plate
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         6591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.1377
_refine_ls_R_factor_gt           0.1086
_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^)+(0.0898P)^2^+6.5468P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2590
_refine_ls_wR_factor_ref         0.2735
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4647
_reflns_number_total             6591
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00487c2.cif
_cod_data_source_block           cu_4418f
_cod_database_code               1553552
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C13(H13), C14(H14),
 C19(H19), C21(H21), C2'(H2'), C3'(H3'), C4'(H4'), C5'(H5'), C6'(H6'),
 C10'(H10'), C13'(H13'), C14'(H14'), C19'(H19'), C21'(H21')
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C23'(H23D,H23E,
 H23F), C24'(H24D,H24E,H24F), C25'(H25D,H25E,H25F)
;
_shelx_res_checksum              50761
_shelx_hkl_checksum              70057
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'