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_1553549
_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         '0.5(C56 H32 Br4)'
_chemical_formula_sum            'C28 H16 Br2'
_chemical_formula_weight         512.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-13
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2016-07-26 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.188(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.802(3)
_cell_length_b                   4.9336(5)
_cell_length_c                   18.875(3)
_cell_measurement_reflns_used    1335
_cell_measurement_temperature    123
_cell_measurement_theta_max      23.83
_cell_measurement_theta_min      2.84
_cell_volume                     2030.2(5)
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS-2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1924
_diffrn_reflns_av_unetI/netI     0.2136
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9384
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.85
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.00
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    4.006
_exptl_absorpt_correction_T_max  0.9154
_exptl_absorpt_correction_T_min  0.7334
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.899
_refine_diff_density_min         -1.620
_refine_diff_density_rms         0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.831
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2450
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      0.831
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0681
_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^)+(0.0760P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.1785
_reflns_number_gt                1112
_reflns_number_total             2450
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6qo00487c2.cif
_cod_data_source_block           3698
_cod_database_code               1553549
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Br \\sim Br1S \\sim C6: within 1.7A with sigma of 0.009 and sigma for terminal
atoms of 0.018
Uanis(C12) \\sim Ueq, Uanis(C12S) \\sim Ueq, Uanis(C13S) \\sim Ueq: with sigma
of 0.009 and sigma for terminal atoms of 0.018
Uanis(Br1S) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.016
3. Others
 Sof(C14)=Sof(H14)=Sof(C10)=Sof(H10)=Sof(C13)=Sof(H13)=Sof(C11)=Sof(H11)=
 Sof(C12)=Sof(H12)=1-FVAR(1)
 Sof(C14S)=Sof(H14S)=Sof(C10S)=Sof(H10S)=Sof(C11S)=Sof(H11S)=Sof(C13S)=
 Sof(H13S)=Sof(C12S)=Sof(H12S)=FVAR(1)
 Sof(Br1S)=1-FVAR(2)
 Sof(Br)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C7(H7), C14S(H14S), C10S(H10S), C11S(H11S), C13S(H13S),
 C12S(H12S), C14(H14), C10(H10), C13(H13), C11(H11), C12(H12)
;
_olex2_submission_special_instructions 'No special instructions were received'