Dibenzo[a,e]pentalenes with Low-Lying LUMO Energy Levels as Potential n-Type Materials.
Grenz, David C.; Schmidt, Maximilian; Kratzert, Daniel; Esser, Birgit; The Journal of organic chemistry 83 (2018) 656–663; doi:10.1021/acs.joc.7b02250

data_4033343
_publ_section_title
;
 Dibenzo[a,e]pentalenes with Low-Lying LUMO Energy Levels as Potential
 n-Type Materials.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              656
_journal_page_last               663
_journal_paper_doi               10.1021/acs.joc.7b02250
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C50 H36 Cl1.64'
_chemical_formula_sum            'C50 H36 Cl1.64'
_chemical_formula_weight         694.83
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-05-16 deposited with the CCDC.
2017-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                76.70(5)
_cell_angle_beta                 71.35(5)
_cell_angle_gamma                68.51(5)
_cell_formula_units_Z            1
_cell_length_a                   8.509(7)
_cell_length_b                   9.549(8)
_cell_length_c                   13.264(11)
_cell_measurement_reflns_used    3342
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.10
_cell_measurement_theta_min      2.65
_cell_volume                     942.3(14)
_computing_cell_refinement       'SAINT V8.38A (BRUKER AXS, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (BRUKER AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      99.98
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6137
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.755
_diffrn_reflns_theta_min         1.634
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           0.6
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.861965
_exptl_absorpt_correction_T_min  0.361066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1140 before and 0.0408 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1883 before and 0.0889 after correction.
 The Ratio of minimum to maximum transmission is 0.42.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 22062 reflections, Rint = 0.0624
 (10387 with I > 3sig(I), Rint = 0.0486)
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         6137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0694P)^2^+0.1486P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1403
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4456
_reflns_number_total             6137
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02250_si_001.cif
_cod_data_source_block           esser_dbp_cn_0m_5
_cod_depositor_comments          'Adding full bibliography for 4033343.cif.'
_cod_database_code               4033343
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.956
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.808(6)
 0.192(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C15(H15), C19(H19),
 C21(H21)
3.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              44191
_shelx_hkl_checksum              85828
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 800'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id DBP_CN
_olex2_submission_special_instructions 'No special instructions were received'