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_1553550
_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         'C36 H32 Br2'
_chemical_formula_sum            'C36 H32 Br2'
_chemical_formula_weight         624.43
_chemical_name_systematic        jm192.1
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-07-26 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                77.981(2)
_cell_angle_beta                 86.017(2)
_cell_angle_gamma                79.287(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0648(5)
_cell_length_b                   11.6684(6)
_cell_length_c                   12.2462(6)
_cell_measurement_reflns_used    6467
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.97
_cell_volume                     1381.44(12)
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker X8-KappaApexII'
_diffrn_measurement_method       'fine slicing \w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23414
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         2.630
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.958
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5911
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0999 before and 0.0426 after correction.
The Ratio of minimum to maximum transmission is 0.7924.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellowish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       plate
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.471
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         6547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0508
_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^)+(0.0765P)^2^+1.2445P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1396
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5052
_reflns_number_total             6547
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00487c2.cif
_cod_data_source_block           4000s
_cod_database_code               1553550
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.603
_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. Others
 Sof(Br1S)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
 Sof(Br2S)=1-FVAR(2)
 Sof(Br2)=FVAR(2)
3.a Aromatic/amide H refined with riding coordinates:
 C26(H26), C32(H32), C28(H28), C6(H6), C2(H2), C29(H29), C11(H11), C23(H23),
 C15(H15), C5(H5), C24(H24), C14(H14), C12(H12), C31(H31)
3.b Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C18(H18A,H18B,H18C), C35(H35A,H35B,H35C), C19(H19A,H19B,
 H19C), C34(H34A,H34B,H34C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              92486
_shelx_hkl_checksum              23414
_olex2_submission_special_instructions 'No special instructions were received'