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_4135340
_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         'C128 H132 O4 Si4, 4(C7 H8)'
_chemical_formula_sum            'C156 H146 O4 Si4'
_chemical_formula_weight         2197.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.020(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   21.0146(9)
_cell_length_b                   17.8252(8)
_cell_length_c                   16.9580(7)
_cell_measurement_reflns_used    9750
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.86
_cell_measurement_theta_min      2.31
_cell_volume                     6352.3(5)
_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  'Bruker SHELXTL Bruker-AXS, Madison WI'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 with PHOTON II detector'
_diffrn_measurement_method       '\f and \w shutterless scans'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7288
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            78979
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.868
_diffrn_reflns_theta_max         24.868
_diffrn_reflns_theta_min         1.536
_diffrn_source
;
Advanced Light Source, station 12.2.1
;
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS, Madison WI'
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       block
_exptl_crystal_F_000             2340
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     786
_refine_ls_number_reflns         10213
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0644
_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^)+(0.0665P)^2^+10.8873P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1687
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8016
_reflns_number_total             10213
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09941_si_003.cif
_cod_data_source_block           hb52318f
_cod_depositor_comments
'Adding full bibliography for 4135339--4135341.cif.'
_cod_database_code               4135340
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C64) \\sim Ueq, Uanis(C68) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: C65(0.5) H65A(0.5) H65B(0.5) C67(0.5) H67A(0.5) H67B(0.5) C63(0.5)
 H63A(0.5) H63B(0.5) C62(0.5) H62A(0.5) H62B(0.5) C66(0.5) H66A(0.5) H66B(0.5)
 C61(0.5) H61A(0.5) H61B(0.5) C68(0.5) H68A(0.5) H68B(0.5) H68C(0.5) C64(0.5)
 H64A(0.5) H64B(0.5) H64C(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C65(H65A,H65B), C67(H67A,
 H67B), C63(H63A,H63B), C62(H62A,H62B), C66(H66A,H66B), C61(H61A,H61B)
4.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C7(H7), C18(H18), C10(H10), C50(H50), C36(H36), C26(H26), C48(H48),
 C13(H13), C29(H29), C35(H35), C11(H11), C27(H27), C22(H22), C21(H21), C20(H20),
  C12(H12), C19(H19), C14(H14), C33(H33), C38(H38), C47(H47), C51(H51),
 C54(H54), C53(H53), C30(H30), C32(H32), C57(H57), C56(H56), C58(H58), C70(H70),
  C77(H77), C72(H72), C74(H74), C78(H78), C73(H73), C71(H71), C79(H79),
 C80(H80), C81(H81)
4.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C40(H40A,H40B,H40C), C39(H39A,H39B,
 H39C), C44(H44A,H44B,H44C), C75(H75A,H75B,H75C), C59(H59A,H59B,H59C), C60(H60A,
 H60B,H60C), C82(H82A,H82B,H82C), C68(H68A,H68B,H68C), C64(H64A,H64B,H64C)
;
_olex2_submission_special_instructions 'No special instructions were received'