Shape-Selective Synthesis of Pentacene Macrocycles and the Effect of Geometry on Singlet Fission.
Bergman, Harrison M.; Kiel, Gavin R.; Witzke, Ryan J.; Nenon, David P.; Schwartzberg, Adam M.; Liu, Yi; Tilley, T. Don; Journal of the American Chemical Society 142 (2020) 19850–19855; doi:10.1021/jacs.0c09941

data_4135341
_publ_section_title
;
 Shape-Selective Synthesis of Pentacene Macrocycles and the Effect of
 Geometry on Singlet Fission.
;
_journal_issue                   47
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              19850
_journal_page_last               19855
_journal_paper_doi               10.1021/jacs.0c09941
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         '6(C H Cl3), C100 H64'
_chemical_formula_sum            'C106 H70 Cl18'
_chemical_formula_weight         1981.72
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-06-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                100.353(2)
_cell_angle_beta                 102.176(2)
_cell_angle_gamma                107.043(2)
_cell_formula_units_Z            1
_cell_length_a                   11.8612(5)
_cell_length_b                   14.1474(7)
_cell_length_c                   14.9784(8)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.59
_cell_measurement_theta_min      2.44
_cell_volume                     2269.2(2)
_computing_cell_refinement       'SAINT V8.38A Bruker-AXS, Madison WI'
_computing_data_collection       'Bruker APEX2 Bruker-AXS, Madison WI'
_computing_data_reduction        'SAINT V8.38A Bruker-AXS, Madison WI'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.884
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_device_type  'Bruker D8 with PHOTON 100 detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7288
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_Laue_measured_fraction_full 0.884
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20363
_diffrn_reflns_point_group_measured_fraction_full 0.884
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        22.617
_diffrn_reflns_theta_max         22.617
_diffrn_reflns_theta_min         1.476
_diffrn_source
;
Advanced Light Source, station 12.2.1
;
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  0.7448
_exptl_absorpt_correction_T_min  0.5595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1644 before and 0.0676 after correction. The Ratio of minimum to maximum transmission is 0.7512. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       needle
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.768
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         4947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.0892
_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^)+(0.0523P)^2^+33.8629P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2729
_refine_ls_wR_factor_ref         0.2902
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3383
_reflns_number_total             4947
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09941_si_002.cif
_cod_data_source_block           hb_43
_cod_depositor_comments
'Adding full bibliography for 4135339--4135341.cif.'
_cod_original_cell_volume        2269.21(19)
_cod_database_code               4135341
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.885
_shelx_estimated_absorpt_t_min   0.834
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: Cl8B(0.5) Cl9B(0.5) Cl9A(0.5) Cl8A(0.5)
3.a Ternary CH refined with riding coordinates:
 C51(H51), C50(H50)
3.b Aromatic/amide H refined with riding coordinates:
 C43(H43), C40(H40), C8(H8), C5(H5), C42(H42), C39(H39), C10(H10), C3(H3),
 C6(H6), C7(H7), C30(H30), C16(H16), C45(H45), C49(H49), C33(H33), C32(H32),
 C46(H46), C48(H48), C14(H14), C20(H20), C24(H24), C29(H29), C23(H23), C19(H19),
  C17(H17), C27(H27), C18(H18), C26(H26)
;
_olex2_submission_special_instructions 'No special instructions were received'