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_1547085
_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         'C52 H50 N2 O4 Si'
_chemical_formula_sum            'C52 H50 N2 O4 Si'
_chemical_formula_weight         795.03
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.800(5)
_cell_length_b                   13.066(3)
_cell_length_c                   16.207(4)
_cell_measurement_reflns_used    12002
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4473
_cell_measurement_theta_min      1.2564
_cell_volume                     4404.6(18)
_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, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 99.7000
_diffrn_measured_fraction_theta_max 27.4473
_diffrn_measurement_details
;
scan:
    Number of images: 35
               Slice: -110.0000 - -92.5000
         Image width: 0.5000
            Exp time: 24.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 45.0421
              2theta: -19.8263
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 24.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 45.0421
              2theta: -19.8263
;
_diffrn_measurement_device
;
?
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0615
_diffrn_orient_matrix_UB_12      0.0456
_diffrn_orient_matrix_UB_13      -0.0014
_diffrn_orient_matrix_UB_21      -0.0366
_diffrn_orient_matrix_UB_22      0.0491
_diffrn_orient_matrix_UB_23      -0.0075
_diffrn_orient_matrix_UB_31      -0.0028
_diffrn_orient_matrix_UB_32      0.0052
_diffrn_orient_matrix_UB_33      0.0477
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710747
_diffrn_reflns_av_R_equivalents  0.0957
_diffrn_reflns_av_unetI/netI     0.0882
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15337
_diffrn_reflns_point_group_measured_fraction_full 0.759
_diffrn_reflns_point_group_measured_fraction_max 0.759
_diffrn_reflns_theta_full        25.198
_diffrn_reflns_theta_max         25.198
_diffrn_reflns_theta_min         1.558
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       plate
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.565
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.063
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 1058 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         6031
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0940
_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^)+(0.1069P)^2^+8.5465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2299
_refine_ls_wR_factor_ref         0.2407
_reflns_Friedel_coverage         0.466
_reflns_Friedel_fraction_full    0.503
_reflns_Friedel_fraction_max     0.503
_reflns_number_gt                5129
_reflns_number_total             6031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02011_si_004.cif
_cod_data_source_block           a
_cod_original_cell_volume        4404.8(17)
_cod_database_code               1547085
_diffrn_number_total             5551
_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(C11A) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C12A) \\sim Ueq, Uanis(C12)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(H10A)=Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=Sof(C11A)=Sof(H11D)=
 Sof(H11E)=Sof(H11F)=1-FVAR(1)
 Sof(H10)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C12)=Sof(H12A)=Sof(H12B)=
 Sof(H12C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C10(H10A), C47(H47), C50(H50)
4.b Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C39(H39A,H39B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C15(H15), C20(H20), C25(H25), C26(H26), C29(H29),
 C30(H30), C43(H43), C44(H44), C45(H45)
4.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C38(H38A,H38B,H38C), C40(H40A,H40B,H40C), C48(H48A,H48B,H48C), C49(H49A,H49B,
 H49C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C12A(H12D,H12E,H12F),
 C11A(H11D,H11E,H11F)
;
_shelx_res_checksum              4316
_shelx_hkl_checksum              57860
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'