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_1547087
_publ_section_title
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 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         'C36 H20 F14 N2 O4 Si'
_chemical_formula_sum            'C36 H20 F14 N2 O4 Si'
_chemical_formula_weight         838.63
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-01-09
_audit_creation_method
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Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5289)
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_audit_update_record
;
????
;
_cell_angle_alpha                90
_cell_angle_beta                 102.583(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.491(11)
_cell_length_b                   16.508(11)
_cell_length_c                   13.190(9)
_cell_measurement_reflns_used    9622
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4814
_cell_measurement_theta_min      1.2652
_cell_volume                     3505(4)
_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(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0924
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22846
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.198
_diffrn_reflns_theta_max         25.198
_diffrn_reflns_theta_min         1.265
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_description       needle
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         6300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.230
_refine_ls_R_factor_all          0.1609
_refine_ls_R_factor_gt           0.1319
_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^)+(0.0452P)^2^+14.1933P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2287
_refine_ls_wR_factor_ref         0.2451
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4897
_reflns_number_total             6300
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02011_si_002.cif
_cod_data_source_block           a_sq
_cod_database_code               1547087
_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.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C29(H29A,H29B), C33(H33A,H33B), C35(H35A,H35B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C13(H13), C18(H18)
2.c Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C36(H36A,H36B,H36C)
;
_shelx_res_checksum              33472
_shelx_hkl_checksum              17356
_shelx_fab_checksum              78505
_olex2_submission_special_instructions 'No special instructions were received'