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_4128442
_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         'C F3 O3 S, C2 H1.67 Cl4, C44 H24 O2'
_chemical_formula_sum            'C47 H25.7 Cl4 F3 O5 S'
_chemical_formula_weight         901.23
_chemical_name_systematic        Ph2-s-PCPL+
_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             2018-08-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-04-25 # Formatted by publCIF
;
_cell_angle_alpha                111.146(5)
_cell_angle_beta                 93.115(5)
_cell_angle_gamma                104.921(5)
_cell_formula_units_Z            2
_cell_length_a                   10.1047(6)
_cell_length_b                   14.1320(7)
_cell_length_c                   14.8352(8)
_cell_measurement_reflns_used    3667
_cell_measurement_temperature    100
_cell_measurement_theta_max      23.1650
_cell_measurement_theta_min      2.4240
_cell_volume                     1883.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -53.20 149.80   0.50   25.00    --  -15.98  73.70-159.59  406
  2  \w    -54.73 148.27   0.50   25.00    --  -17.51  73.70  29.07  406
  3  \w    -54.73 118.27   0.50   25.00    --  -17.51  73.70 -59.91  346
  4  \w    -54.73 148.27   0.50   25.00    --  -17.51  73.70 134.27  406
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0491929000
_diffrn_orient_matrix_UB_12      -0.0088635000
_diffrn_orient_matrix_UB_13      0.0295613000
_diffrn_orient_matrix_UB_21      -0.0214836000
_diffrn_orient_matrix_UB_22      0.0308811000
_diffrn_orient_matrix_UB_23      0.0426976000
_diffrn_orient_matrix_UB_31      -0.0504033000
_diffrn_orient_matrix_UB_32      -0.0463149000
_diffrn_orient_matrix_UB_33      -0.0017493000
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.1042
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            38938
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.792
_diffrn_reflns_theta_min         1.618
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.437
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_description       block
_exptl_crystal_F_000             917
_exptl_crystal_recrystallization_method Diffusion
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.066
_refine_diff_density_min         -1.646
_refine_diff_density_rms         0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         10414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1645
_refine_ls_R_factor_gt           0.0969
_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^)+(0.1764P)^2^+3.1221P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2612
_refine_ls_wR_factor_ref         0.3193
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6182
_reflns_number_total             10414
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13300_si_003.cif
_cod_data_source_block           c47
_cod_original_cell_volume        1883.55(19)
_cod_original_formula_sum        'C47 H25.70 Cl4 F3 O5 S'
_cod_database_code               4128442
_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.
;
_chemical_oxdiff_formula         'C22 H20 O2'
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H0AB)=Sof(Cl0B)=Sof(S0AB)=1-FVAR(1)
 Sof(S0AA)=Sof(Cl0A)=Sof(H0AA)=Sof(H1)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C0AA(H0AA), C0AA(H0AB), C1(H1)
3.b Aromatic/amide H refined with riding coordinates:
 C8BA(H8BA), C9BA(H9BA), C0CA(H0CA), C1CA(H1CA), C4CA(H4CA), C5CA(H5CA),
 C9CA(H9CA), C0DA(H0DA), C1DA(H1DA), C2DA(H2DA), C3DA(H3DA), C4DA(H4DA),
 C6DA(H6DA), C7DA(H7DA), C8DA(H8DA), C9DA(H9DA), C0EA(H0EA), C1EA(H1EA),
 C2EA(H2EA), C3EA(H3EA), C4EA(H4EA), C5EA(H5EA), C6EA(H6EA), C7EA(H7EA)
;
_olex2_exptl_crystal_mounting_method 'Paratone Oil'
_olex2_submission_original_sample_id Ph2-s-PCPL+
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.040
_oxdiff_exptl_absorpt_empirical_full_min 0.966
_publcif_funding_html
;
;