Aerobic Co-/ N-Hydroxysuccinimide-Catalyzed Oxidation of p-Tolylsiloxanes to p-Carboxyphenylsiloxanes: Synthesis of Functionalized Siloxanes as Promising Building Blocks for Siloxane-Based Materials.
Goncharova, Irina K.; Silaeva, Kseniia P.; Arzumanyan, Ashot V.; Anisimov, Anton A.; Milenin, Sergey A.; Novikov, Roman A.; Solyev, Pavel N.; Tkachev, Yaroslav V.; Volodin, Alexander D.; Korlyukov, Alexander A.; Muzafarov, Aziz M.; Journal of the American Chemical Society 141 (2019) 2143–2151; doi:10.1021/jacs.8b12600

data_4127913
_publ_section_title
;
 Aerobic Co-/ N-Hydroxysuccinimide-Catalyzed Oxidation of p-Tolylsiloxanes
 to p-Carboxyphenylsiloxanes: Synthesis of Functionalized Siloxanes as
 Promising Building Blocks for Siloxane-Based Materials.
;
_journal_issue                   5
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2143
_journal_page_last               2151
_journal_paper_doi               10.1021/jacs.8b12600
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C12 H20 O3 Si2'
_chemical_formula_sum            'C12 H20 O3 Si2'
_chemical_formula_weight         268.46
_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             2018-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                81.306(6)
_cell_angle_beta                 81.036(6)
_cell_angle_gamma                85.912(5)
_cell_formula_units_Z            4
_cell_length_a                   7.2406(16)
_cell_length_b                   12.798(3)
_cell_length_c                   17.089(4)
_cell_measurement_reflns_used    1806
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.027
_cell_measurement_theta_min      2.155
_cell_volume                     1544.4(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.1123
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12741
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.526
_diffrn_reflns_theta_min         1.612
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0754 before and 0.0475 after correction. The Ratio of minimum to maximum transmission is 0.7860. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         9129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.0717
_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^)+(0.0891P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1707
_refine_ls_wR_factor_ref         0.2003
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5416
_reflns_number_total             9129
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b12600_si_002.cif
_cod_data_source_block           i8473
_cod_database_code               4127913
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.942
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2AA(0.048) H2(0.052) H6(0.027) H2A(0.032) H3(0.031) H5(0.027)
 H5A(0.03) H6A(0.03) H3A(0.028) H2AB(0.028) H9A(0.044) H9B(0.044) H9C(0.044)
 H8A(0.049) H8B(0.049) H8C(0.049) H8AA(0.046) H8AB(0.046) H8AC(0.046)
 H12A(0.056) H12B(0.056) H12C(0.056) H10A(0.051) H10B(0.051) H10C(0.051)
 H9AA(0.052) H9AB(0.052) H9AC(0.052) H11A(0.08) H11B(0.08) H11C(0.08)
 H10D(0.078) H10E(0.078) H10F(0.078) H11D(0.09) H11E(0.09) H11F(0.09)
 H12D(0.104) H12E(0.104) H12F(0.104)
 Fixed X: H2AA(0.4099) H2(1.084) H6(1.0972) H2A(0.6018) H3(0.7518) H5(1.2479)
 H5A(0.2728) H6A(0.4346) H3A(0.742) H2AB(0.8998) H9A(0.5023) H9B(0.4763)
 H9C(0.6467) H8A(0.6494) H8B(0.4698) H8C(0.5187) H8AA(0.9188) H8AB(1.0755)
 H8AC(1.044) H12A(1.2832) H12B(1.3061) H12C(1.2649) H10A(0.7985) H10B(1.0001)
 H10C(0.9749) H9AA(0.9817) H9AB(1.0196) H9AC(0.8302) H11A(0.9136) H11B(0.9484)
 H11C(0.753) H10D(0.7912) H10E(0.6036) H10F(0.6471) H11D(0.466) H11E(0.4477)
 H11F(0.6501) H12D(0.3017) H12E(0.2294) H12F(0.2242)
 Fixed Y: H2AA(0.5931) H2(0.6429) H6(0.3497) H2A(0.4821) H3(0.5593) H5(0.4226)
 H5A(0.8834) H6A(0.9981) H3A(0.6903) H2AB(0.8034) H9A(0.2248) H9B(0.2662)
 H9C(0.1847) H8A(0.5278) H8B(0.4894) H8C(0.4436) H8AA(1.1232) H8AB(1.0309)
 H8AC(1.1248) H12A(0.3283) H12B(0.2537) H12C(0.2032) H10A(0.3916) H10B(0.3671)
 H10C(0.4536) H9AA(0.965) H9AB(0.8713) H9AC(0.8774) H11A(0.0998) H11B(0.1303)
 H11C(0.1633) H10D(1.2395) H10E(1.2883) H10F(1.3126) H11D(0.98) H11E(1.0767)
 H11F(1.027) H12D(1.2191) H12E(1.2235) H12F(1.1155)
 Fixed Z: H2AA(0.4632) H2(0.4668) H6(0.2044) H2A(0.2963) H3(0.383) H5(0.2922)
 H5A(0.5691) H6A(0.6245) H3A(0.5419) H2AB(0.6009) H9A(0.1665) H9B(0.2515)
 H9C(0.2279) H8A(0.0935) H8B(0.1555) H8C(0.0721) H8AA(0.5573) H8AB(0.5729)
 H8AC(0.6265) H12A(0.0325) H12B(-0.036) H12C(0.0562) H10A(-0.072) H10B(-0.1208)
 H10C(-0.061) H9AA(0.7794) H9AB(0.7258) H9AC(0.7876) H11A(0.0472) H11B(-0.0481)
 H11C(0.0021) H10D(0.7927) H10E(0.8392) H10F(0.7437) H11D(0.8707) H11E(0.9213)
 H11F(0.8902) H12D(0.7055) H12E(0.7984) H12F(0.7623)
;
_shelx_res_checksum              30008
_shelx_hkl_checksum              38638
_olex2_submission_special_instructions 'No special instructions were received'