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_4034304
_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         'C42 H50 O S2 Si2'
_chemical_formula_sum            'C42 H50 O S2 Si2'
_chemical_formula_weight         691.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-01
_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
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.6849(6)
_cell_length_b                   26.3848(12)
_cell_length_c                   37.699(2)
_cell_measurement_reflns_used    7453
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.2000
_cell_measurement_theta_min      1.6370
_cell_volume                     7644.0(8)
_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 1.000
_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  0.1133
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            46355
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         1.635
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05684
_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            orange
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       plate
_exptl_crystal_F_000             2960
_exptl_crystal_size_max          0.621
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         8736
_refine_ls_number_restraints     319
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1606
_refine_ls_R_factor_gt           0.0909
_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^)+(0.0895P)^2^+8.2476P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1926
_refine_ls_wR_factor_ref         0.2299
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4875
_reflns_number_total             8736
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00579_si_002.cif
_cod_data_source_block           mx7343
_cod_original_cell_volume        7644.1(8)
_cod_database_code               4034304
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.869
_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, All C(H,H,H,H,H,H) groups, All O(H) groups
2. Restrained distances
 C27-C26 = C27A-C26A = C28A-C26A = C28-C26
 1.54 with sigma of 0.01
 C36A-C34A = C35A-C34A = C35-C34 = C36-C34
 1.54 with sigma of 0.01
 C31A-C29A = C31-C29 = C30A-C29A = C30-C29
 1.54 with sigma of 0.01
3. Rigid bond restraints
 O1, C10
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C26 \\sim C27 \\sim C28 \\sim C26A \\sim C27A \\sim C28A: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
C34 \\sim C35 \\sim C36 \\sim C34A \\sim C35A \\sim C36A: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
C29A \\sim C30 \\sim C31 \\sim C29 \\sim C30A \\sim C31A: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C26A)
\\sim Ueq, Uanis(C27A) \\sim Ueq, Uanis(C28A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C34) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C34A)
\\sim Ueq, Uanis(C35A) \\sim Ueq, Uanis(C36A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C37) \\sim Ueq, Uanis(C37A) \\sim Ueq, Uanis(C40A) \\sim Ueq, Uanis(C40)
\\sim Ueq, Uanis(C29A) \\sim Ueq, Uanis(C29) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C29A) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C29)
\\sim Ueq, Uanis(C30A) \\sim Ueq, Uanis(C31A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
5. Others
 Sof(C26A)=Sof(H26A)=Sof(C27A)=Sof(H27D)=Sof(H27E)=Sof(H27F)=Sof(C28A)=
 Sof(H28D)=Sof(H28E)=Sof(H28F)=1-FVAR(1)
 Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=Sof(C28)=Sof(H28A)=
 Sof(H28B)=Sof(H28C)=FVAR(1)
 Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30D)=Sof(H30E)=Sof(H30F)=Sof(C31A)=
 Sof(H31D)=Sof(H31E)=Sof(H31F)=1-FVAR(2)
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=
 Sof(C29)=Sof(H29)=FVAR(2)
 Sof(H41D)=Sof(H41E)=Sof(H41F)=Sof(H42D)=Sof(H42E)=Sof(H42F)=Sof(C40A)=
 Sof(H40A)=1-FVAR(3)
 Sof(C40)=Sof(H40)=Sof(H41A)=Sof(H41B)=Sof(H41C)=Sof(H42A)=Sof(H42B)=Sof(H42C)=
 FVAR(3)
 Sof(H38D)=Sof(H38E)=Sof(H38F)=Sof(H39D)=Sof(H39E)=Sof(H39F)=Sof(C37A)=
 Sof(H37A)=1-FVAR(4)
 Sof(C37)=Sof(H37)=Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(H39A)=Sof(H39B)=Sof(H39C)=
 FVAR(4)
 Sof(C34A)=Sof(H34A)=Sof(C35A)=Sof(H35D)=Sof(H35E)=Sof(H35F)=Sof(C36A)=
 Sof(H36D)=Sof(H36E)=Sof(H36F)=1-FVAR(5)
 Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(H35C)=Sof(C36)=Sof(H36A)=
 Sof(H36B)=Sof(H36C)=FVAR(5)
6.a Ternary CH refined with riding coordinates:
 C23(H23), C26(H26), C29A(H29A), C34(H34), C37(H37), C40(H40), C26A(H26A),
 C29(H29), C40A(H40A), C37A(H37A), C34A(H34A)
6.b Me refined with riding coordinates:
 C42(H42A,H42B,H42C)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C12(H12), C13(H13), C16(H16), C17(H17)
6.d 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), C38(H38D,H38E,H38F), C39(H39A,H39B,H39C),
 C39(H39D,H39E,H39F), C41(H41A,H41B,H41C), C41(H41D,H41E,H41F), C42(H42D,H42E,
 H42F), C27A(H27D,H27E,H27F), C28A(H28D,H28E,H28F), C35A(H35D,H35E,H35F),
 C36A(H36D,H36E,H36F), C30A(H30D,H30E,H30F), C31A(H31D,H31E,H31F)
6.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              12493
_shelx_hkl_checksum              64005
_olex2_submission_special_instructions 'No special instructions were received'