A Concise Synthetic Strategy for Accessing Ambient Stable Bisphenalenyls toward Achieving Electroactive Open-Shell π-Conjugated Materials.
Wehrmann, Caleb M.; Charlton, Ryan T.; Chen, Mark S.; Journal of the American Chemical Society 141 (2019) 3240–3248; doi:10.1021/jacs.8b13300

data_4128443
_publ_section_title
;
 A Concise Synthetic Strategy for Accessing Ambient Stable Bisphenalenyls
 toward Achieving Electroactive Open-Shell \p-Conjugated Materials.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3240
_journal_page_last               3248
_journal_paper_doi               10.1021/jacs.8b13300
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         '2(C H Cl3), C44 H24'
_chemical_formula_sum            'C46 H26 Cl6'
_chemical_formula_weight         791.37
_chemical_name_systematic        Ph2-IDPL
_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             2018-08-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-12 # Formatted by publCIF
;
_cell_angle_alpha                106.928(5)
_cell_angle_beta                 111.639(6)
_cell_angle_gamma                92.186(5)
_cell_formula_units_Z            1
_cell_length_a                   9.0833(6)
_cell_length_b                   9.8014(6)
_cell_length_c                   11.3650(7)
_cell_measurement_reflns_used    4306
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.153
_cell_volume                     887.63(11)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17956
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.811
_diffrn_reflns_theta_min         2.041
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.520
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'metallic dark green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_recrystallization_method 'evaporated from chloroform'
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.401
_exptl_crystal_size_min          0.399
_refine_diff_density_max         1.330
_refine_diff_density_min         -1.085
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0822
_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^)+(0.1440P)^2^+1.2111P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2435
_refine_ls_wR_factor_ref         0.2561
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4011
_reflns_number_total             4865
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13300_si_002.cif
_cod_data_source_block           a
_cod_database_code               4128443
_shelx_shelxl_version_number     2018/3
_audit_contact_letter
;
Please consider this CIF for publication. I certify that this contibution is the
original work of those listed as authors; that it has not been published
before (in any language or medium) and is not being considered for publication
elsewhere; that all authors concur with and are aware of the submission; that
all workers involved in the study are listed as authors or given proper credit
in the acknowledgements; that I have obtained permission for and acknowledged
the source of any excerpts from other copyright works; and that to the best of
my knowledge the paper contains no statements which are libellous, unlawful or
in any way actionable. All coauthors have made significant scientific
contributions to the work reported, including the ideas and their execution,
and share responsibility and accountability for the results.
;
_shelx_estimated_absorpt_t_max   0.819
_shelx_estimated_absorpt_t_min   0.767
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H(0.053) H13(0.029) H12(0.026) H11(0.025) H9(0.025) H8(0.027)
 H7(0.028) H6(0.028) H5(0.029) H4(0.032) H3(0.044) H2(0.038) H1(0.045)
 Fixed X: H(0.38349) H13(0.416371) H12(0.069961) H11(0.84151) H9(0.096329)
 H8(0.827469) H7(0.192692) H6(0.661919) H5(0.798596) H4(0.931494) H3(1.20056)
 H2(1.066814) H1(1.267416)
 Fixed Y: H(0.657007) H13(0.886268) H12(0.447831) H11(0.368511) H9(0.205286)
 H8(0.613498) H7(0.715202) H6(0.818071) H5(0.071367) H4(0.091435) H3(0.146585)
 H2(0.129591) H1(0.164125)
 Fixed Z: H(0.352858) H13(0.201726) H12(-0.081459) H11(0.273505) H9(-0.125424)
 H8(0.329332) H7(0.046582) H6(0.301097) H5(0.348029) H4(0.049714) H3(0.200272)
 H2(0.497466) H1(0.423654)
;
_olex2_exptl_crystal_mounting_method 'paratone oil '
_olex2_submission_original_sample_id Ph2-IDPL
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
;
;