Palladium-Catalyzed Si-C Bond Formation toward Sila-Annulated Perylene Diimides.
Ma, Zetong; Xiao, Chengyi; Liu, Chunming; Meng, Dong; Jiang, Wei; Wang, Zhaohui; Organic letters 19 (2017) 4331–4334; doi:10.1021/acs.orglett.7b02011

data_1547088
_publ_section_title
;
 Palladium-Catalyzed Si-C Bond Formation toward Sila-Annulated Perylene
 Diimides.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4331
_journal_page_last               4334
_journal_paper_doi               10.1021/acs.orglett.7b02011
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C56 H58 N2 O4 Si2, 2(C7 H8)'
_chemical_formula_sum            'C70 H74 N2 O4 Si2'
_chemical_formula_weight         1063.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-01-10
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5289)
;
_audit_update_record
;
????
;
_cell_angle_alpha                67.88(3)
_cell_angle_beta                 82.56(3)
_cell_angle_gamma                70.67(3)
_cell_formula_units_Z            2
_cell_length_a                   12.123(2)
_cell_length_b                   15.118(3)
_cell_length_c                   18.055(4)
_cell_measurement_reflns_used    7681
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4709
_cell_measurement_theta_min      1.5279
_cell_volume                     2892.6(13)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            41971
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         1.217
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     782
_refine_ls_number_reflns         13150
_refine_ls_number_restraints     276
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0959
_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^)+(0.0870P)^2^+2.6203P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2188
_refine_ls_wR_factor_ref         0.2309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10959
_reflns_number_total             13150
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02011_si_005.cif
_cod_data_source_block           mx5504
_cod_database_code               1547088
_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. Restrained distances
 C69A-C64A = C65A-C64A = C66A-C65A = C67A-C66A = C68A-C67A = C69A-C68A
 1.39 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C64 \\sim C66 \\sim C67 \\sim C68 \\sim C69 \\sim C70 \\sim C67A \\sim C70A
\\sim C68A \\sim C69A \\sim C64A \\sim C66A \\sim C65A \\sim C65: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C65) \\sim Ueq, Uanis(C64) \\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(C66)
\\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C67) \\sim Ueq, Uanis(C70) \\sim Ueq,
Uanis(C66A) \\sim Ueq, Uanis(C67A) \\sim Ueq, Uanis(C70A) \\sim Ueq,
Uanis(C68A) \\sim Ueq, Uanis(C69A) \\sim Ueq, Uanis(C65A) \\sim Ueq,
Uanis(C64A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C67A)=Sof(C70A)=Sof(H70D)=Sof(H70E)=Sof(H70F)=Sof(C68A)=Sof(H68A)=
 Sof(C69A)=Sof(H69A)=Sof(C64A)=Sof(H64A)=Sof(C65A)=Sof(H65A)=Sof(C66A)=
 Sof(H66A)=1-FVAR(1)
 Sof(C64)=Sof(H64)=Sof(C65)=Sof(H65)=Sof(C66)=Sof(H66)=Sof(C67)=Sof(C68)=
 Sof(H68)=Sof(C69)=Sof(H69)=Sof(C70)=Sof(H70A)=Sof(H70B)=Sof(H70C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C31(H31), C34(H34), C43(H43), C46(H46)
5.b Secondary CH2 refined with riding coordinates:
 C49(H49A,H49B), C51(H51A,H51B), C53(H53A,H53B), C55(H55A,H55B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C13(H13), C18(H18), C27(H27), C28(H28), C29(H29), C39(H39),
 C40(H40), C41(H41), C58(H58), C59(H59), C60(H60), C61(H61), C62(H62), C64(H64),
  C65(H65), C66(H66), C68(H68), C69(H69), C68A(H68A), C69A(H69A), C64A(H64A),
 C65A(H65A), C66A(H66A)
5.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C47(H47A,H47B,H47C), C48(H48A,
 H48B,H48C), C50(H50A,H50B,H50C), C52(H52A,H52B,H52C), C54(H54A,H54B,H54C),
 C56(H56A,H56B,H56C), C63(H63A,H63B,H63C), C70(H70A,H70B,H70C), C70A(H70D,H70E,
 H70F)
;
_shelx_res_checksum              66752
_shelx_hkl_checksum              22857
_olex2_submission_special_instructions 'No special instructions were received'