Isomeric Pyrenodithiophenediones and Their Derivatives: Synthesis, Reactivity, and Device Performance.
Zhou, Chenxi; Gu, Wen; Zhang, Guowei; Liu, Lele; Lv, Aifeng; Zhang, Lei; The Journal of organic chemistry 84 (2019) 5936–5942; doi:10.1021/acs.joc.9b00579

data_4034305
_publ_section_title
;
 Isomeric Pyrenodithiophenediones and Their Derivatives: Synthesis,
 Reactivity, and Device Performance.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5936
_journal_page_last               5942
_journal_paper_doi               10.1021/acs.joc.9b00579
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C64 H90 S2 Si4'
_chemical_formula_sum            'C64 H90 S2 Si4'
_chemical_formula_weight         1035.83
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                99.940(3)
_cell_angle_beta                 93.813(3)
_cell_angle_gamma                95.177(3)
_cell_formula_units_Z            2
_cell_length_a                   8.5273(3)
_cell_length_b                   17.7790(7)
_cell_length_c                   20.8815(8)
_cell_measurement_reflns_used    9489
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5310
_cell_measurement_theta_min      1.6460
_cell_volume                     3094.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_av_unetI/netI     0.1139
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            41134
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.665
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.9d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.112
_exptl_crystal_description       rod
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.331
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.087
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     745
_refine_ls_number_reflns         14161
_refine_ls_number_restraints     276
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1516
_refine_ls_R_factor_gt           0.0746
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.6161P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1738
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7668
_reflns_number_total             14161
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00579_si_003.cif
_cod_data_source_block           mx7492a
_cod_database_code               4034305
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.937
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C34 \\sim C35 \\sim C36 \\sim C34A \\sim C36A \\sim C35A: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
C40 \\sim C41 \\sim C42 \\sim C40A \\sim C42A \\sim C41A: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
C37 \\sim C38 \\sim C39 \\sim C37A \\sim C38A \\sim C39A: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C40) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C40A)
\\sim Ueq, Uanis(C42A) \\sim Ueq, Uanis(C41A) \\sim Ueq, Uanis(C34) \\sim Ueq,
Uanis(C35) \\sim Ueq, Uanis(C34A) \\sim Ueq, Uanis(C35A) \\sim Ueq, Uanis(C36)
\\sim Ueq, Uanis(C36A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C37) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(C37A)
\\sim Ueq, Uanis(C38A) \\sim Ueq, Uanis(C39A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
3. Others
 Sof(C40A)=Sof(H40A)=Sof(C42A)=Sof(H42D)=Sof(H42E)=Sof(H42F)=Sof(C41A)=
 Sof(H41D)=Sof(H41E)=Sof(H41F)=1-FVAR(1)
 Sof(C40)=Sof(H40)=Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(H41C)=Sof(C42)=Sof(H42A)=
 Sof(H42B)=Sof(H42C)=FVAR(1)
 Sof(C34A)=Sof(H34A)=Sof(C36A)=Sof(H36D)=Sof(H36E)=Sof(H36F)=Sof(C35A)=
 Sof(H35D)=Sof(H35E)=Sof(H35F)=1-FVAR(2)
 Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(H35C)=Sof(C36)=Sof(H36A)=
 Sof(H36B)=Sof(H36C)=FVAR(2)
 Sof(C37A)=Sof(H37A)=Sof(C38A)=Sof(H38D)=Sof(H38E)=Sof(H38F)=Sof(C39A)=
 Sof(H39D)=Sof(H39E)=Sof(H39F)=1-FVAR(3)
 Sof(C37)=Sof(H37)=Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(C39)=Sof(H39A)=
 Sof(H39B)=Sof(H39C)=FVAR(3)
4.a Ternary CH refined with riding coordinates:
 C23(H23), C26(H26), C29(H29), C34(H34), C37(H37), C40(H40), C45(H45),
 C48(H48), C51(H51), C56(H56), C59(H59), C62(H62), C40A(H40A), C34A(H34A),
 C37A(H37A)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C11(H11), C12(H12), C17(H17)
4.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C35(H35A,H35B,H35C), C36(H36A,
 H36B,H36C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C41(H41A,H41B,H41C),
 C42(H42A,H42B,H42C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C49(H49A,H49B,
 H49C), C50(H50A,H50B,H50C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C57(H57A,
 H57B,H57C), C58(H58A,H58B,H58C), C60(H60A,H60B,H60C), C61(H61A,H61B,H61C),
 C63(H63A,H63B,H63C), C64(H64A,H64B,H64C), C42A(H42D,H42E,H42F), C41A(H41D,H41E,
 H41F), C36A(H36D,H36E,H36F), C35A(H35D,H35E,H35F), C38A(H38D,H38E,H38F),
 C39A(H39D,H39E,H39F)
;
_shelx_res_checksum              83337
_shelx_hkl_checksum              47049
_olex2_submission_special_instructions 'No special instructions were received'