#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/85/4518536.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4518536
loop_
_publ_author_name
'Zhang, Liangliang'
'Oestreich, Martin'
_publ_section_title
;
 Diastereotopic Group-Selective Intramolecular Aldol Reactions Initiated
 by Enantioselective Conjugate Silylation: Diastereodivergence Controlled
 by the Silicon Nucleophile
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              3516
_journal_page_last               3522
_journal_paper_doi               10.1021/acscatal.1c00436
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H30 O3 Si'
_chemical_formula_weight         406.58
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_cell_angle_alpha                90.00
_cell_angle_beta                 102.822(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.4612(6)
_cell_length_b                   6.7009(3)
_cell_length_c                   15.9349(10)
_cell_measurement_reflns_used    1341
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.0400
_cell_measurement_theta_min      4.3030
_cell_volume                     1089.17(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5435
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3935
_diffrn_reflns_theta_full        67.47
_diffrn_reflns_theta_max         67.47
_diffrn_reflns_theta_min         2.84
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.129
_exptl_absorpt_correction_T_max  0.9756
_exptl_absorpt_correction_T_min  0.6933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         2988
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0379P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0938
_reflns_number_gt                2525
_reflns_number_total             2988
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs1c00436_si_002.cif
_cod_data_source_block           cu-3966
_cod_depositor_comments          'Adding full bibliography for 4518536.cif.'
_cod_original_cell_volume        1089.17(10)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               4518536
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.08582(8) 0.27399(14) 0.22593(6) 0.0307(2) Uani 1 1 d . . .
O1 O 0.5589(2) 0.2418(3) 0.29367(14) 0.0277(5) Uani 1 1 d . . .
H1 H 0.512(3) 0.181(6) 0.311(2) 0.033 Uiso 1 1 d . . .
O2 O 0.4557(2) 0.9033(3) 0.36929(13) 0.0296(5) Uani 1 1 d . . .
O3 O 0.3599(2) 0.1272(3) 0.14511(14) 0.0316(5) Uani 1 1 d . . .
C1 C 0.2632(3) 0.3321(4) 0.27897(19) 0.0250(7) Uani 1 1 d . . .
H1A H 0.3041 0.2032 0.3027 0.030 Uiso 1 1 calc R . .
C2 C 0.2651(3) 0.4693(5) 0.3566(2) 0.0299(8) Uani 1 1 d . . .
H2A H 0.2337 0.6036 0.3356 0.036 Uiso 1 1 calc R . .
H2B H 0.2042 0.4159 0.3905 0.036 Uiso 1 1 calc R . .
C3 C 0.4016(3) 0.4876(5) 0.41459(19) 0.0279(7) Uani 1 1 d . . .
H3A H 0.4263 0.3578 0.4433 0.033 Uiso 1 1 calc R . .
H3B H 0.3989 0.5876 0.4599 0.033 Uiso 1 1 calc R . .
C4 C 0.5065(3) 0.5487(5) 0.36667(18) 0.0233(7) Uani 1 1 d . . .
C5 C 0.5017(3) 0.4351(4) 0.28114(19) 0.0231(7) Uani 1 1 d . . .
C6 C 0.3565(3) 0.4250(5) 0.22651(18) 0.0228(7) Uani 1 1 d . . .
H6A H 0.3265 0.5645 0.2109 0.027 Uiso 1 1 calc R . .
C7 C 0.5007(3) 0.7622(5) 0.33683(18) 0.0239(6) Uani 1 1 d . . .
C8 C 0.5634(3) 0.7794(5) 0.25951(18) 0.0247(6) Uani 1 1 d . . .
H8A H 0.6465 0.8555 0.2746 0.030 Uiso 1 1 calc R . .
H8B H 0.5035 0.8469 0.2110 0.030 Uiso 1 1 calc R . .
C9 C 0.5889(3) 0.5622(4) 0.2361(2) 0.0247(7) Uani 1 1 d . . .
H9A H 0.5646 0.5423 0.1730 0.030 Uiso 1 1 calc R . .
H9B H 0.6825 0.5270 0.2571 0.030 Uiso 1 1 calc R . .
C10 C 0.6431(3) 0.5250(5) 0.42825(19) 0.0308(8) Uani 1 1 d . . .
H10A H 0.6451 0.6003 0.4812 0.046 Uiso 1 1 calc R . .
H10B H 0.7108 0.5762 0.4002 0.046 Uiso 1 1 calc R . .
H10C H 0.6596 0.3836 0.4422 0.046 Uiso 1 1 calc R . .
C11 C 0.3506(3) 0.3099(5) 0.1435(2) 0.0245(7) Uani 1 1 d . . .
C12 C 0.3315(3) 0.4166(5) 0.0589(2) 0.0255(7) Uani 1 1 d . . .
C13 C 0.3544(3) 0.6206(5) 0.0507(2) 0.0280(7) Uani 1 1 d . . .
H13A H 0.3739 0.7025 0.1006 0.034 Uiso 1 1 calc R . .
C14 C 0.3488(3) 0.7044(5) -0.0295(2) 0.0339(8) Uani 1 1 d . . .
H14A H 0.3678 0.8421 -0.0340 0.041 Uiso 1 1 calc R . .
C15 C 0.3158(3) 0.5891(5) -0.1029(2) 0.0331(8) Uani 1 1 d . . .
H15A H 0.3147 0.6459 -0.1577 0.040 Uiso 1 1 calc R . .
C16 C 0.2841(3) 0.3893(6) -0.0961(2) 0.0332(8) Uani 1 1 d . . .
H16A H 0.2553 0.3116 -0.1466 0.040 Uiso 1 1 calc R . .
C17 C 0.2943(3) 0.3034(5) -0.01652(19) 0.0296(7) Uani 1 1 d . . .
H17A H 0.2759 0.1653 -0.0126 0.036 Uiso 1 1 calc R . .
C18 C 0.0247(3) 0.1276(5) 0.31034(19) 0.0273(7) Uani 1 1 d . . .
C19 C 0.1031(3) -0.0201(5) 0.3579(2) 0.0332(8) Uani 1 1 d . . .
H19A H 0.1881 -0.0438 0.3480 0.040 Uiso 1 1 calc R . .
C20 C 0.0602(3) -0.1333(5) 0.4194(2) 0.0357(8) Uani 1 1 d . . .
H20A H 0.1156 -0.2334 0.4505 0.043 Uiso 1 1 calc R . .
C21 C -0.0632(3) -0.1009(5) 0.4358(2) 0.0331(8) Uani 1 1 d . . .
H21A H -0.0929 -0.1775 0.4779 0.040 Uiso 1 1 calc R . .
C22 C -0.1418(3) 0.0453(5) 0.3894(2) 0.0325(8) Uani 1 1 d . . .
H22A H -0.2269 0.0681 0.3994 0.039 Uiso 1 1 calc R . .
C23 C -0.0985(3) 0.1589(5) 0.32861(19) 0.0306(8) Uani 1 1 d . . .
H23A H -0.1537 0.2605 0.2986 0.037 Uiso 1 1 calc R . .
C24 C -0.0108(4) 0.5098(6) 0.1997(3) 0.0504(10) Uani 1 1 d . . .
H24A H -0.1011 0.4772 0.1708 0.076 Uiso 1 1 calc R . .
H24B H 0.0290 0.5925 0.1616 0.076 Uiso 1 1 calc R . .
H24C H -0.0108 0.5831 0.2529 0.076 Uiso 1 1 calc R . .
C25 C 0.0625(4) 0.1157(7) 0.1271(2) 0.0491(11) Uani 1 1 d . . .
H25A H -0.0292 0.0727 0.1103 0.074 Uiso 1 1 calc R . .
H25B H 0.1195 -0.0017 0.1389 0.074 Uiso 1 1 calc R . .
H25C H 0.0850 0.1932 0.0802 0.074 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 Si1 C24 109.1(2) . . ?
C25 Si1 C18 107.71(16) . . ?
C24 Si1 C18 110.27(16) . . ?
C25 Si1 C1 115.00(15) . . ?
C24 Si1 C1 110.59(16) . . ?
C18 Si1 C1 103.97(13) . . ?
C2 C1 C6 107.2(2) . . ?
C2 C1 Si1 108.5(2) . . ?
C6 C1 Si1 120.8(2) . . ?
C3 C2 C1 112.3(3) . . ?
C2 C3 C4 113.5(2) . . ?
C7 C4 C3 115.5(3) . . ?
C7 C4 C10 105.3(3) . . ?
C3 C4 C10 108.7(3) . . ?
C7 C4 C5 101.4(2) . . ?
C3 C4 C5 114.9(3) . . ?
C10 C4 C5 110.6(3) . . ?
O1 C5 C9 107.1(2) . . ?
O1 C5 C4 113.1(2) . . ?
C9 C5 C4 103.4(2) . . ?
O1 C5 C6 111.3(2) . . ?
C9 C5 C6 111.4(2) . . ?
C4 C5 C6 110.2(2) . . ?
C11 C6 C1 110.9(2) . . ?
C11 C6 C5 110.5(2) . . ?
C1 C6 C5 111.4(2) . . ?
O2 C7 C4 126.5(3) . . ?
O2 C7 C8 124.0(3) . . ?
C4 C7 C8 109.5(3) . . ?
C7 C8 C9 104.7(3) . . ?
C5 C9 C8 104.9(2) . . ?
O3 C11 C12 119.2(3) . . ?
O3 C11 C6 120.0(3) . . ?
C12 C11 C6 120.8(3) . . ?
C13 C12 C17 118.0(3) . . ?
C13 C12 C11 123.9(3) . . ?
C17 C12 C11 118.0(3) . . ?
C14 C13 C12 120.6(3) . . ?
C15 C14 C13 120.4(3) . . ?
C14 C15 C16 119.5(3) . . ?
C17 C16 C15 120.3(3) . . ?
C16 C17 C12 121.0(3) . . ?
C19 C18 C23 116.8(3) . . ?
C19 C18 Si1 120.2(2) . . ?
C23 C18 Si1 123.0(3) . . ?
C20 C19 C18 121.8(3) . . ?
C21 C20 C19 120.4(3) . . ?
C22 C21 C20 118.5(3) . . ?
C21 C22 C23 121.0(3) . . ?
C22 C23 C18 121.5(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 C25 1.869(4) . ?
Si1 C24 1.872(4) . ?
Si1 C18 1.887(3) . ?
Si1 C1 1.901(3) . ?
O1 C5 1.422(4) . ?
O2 C7 1.221(4) . ?
O3 C11 1.228(4) . ?
C1 C2 1.537(4) . ?
C1 C6 1.549(4) . ?
C2 C3 1.524(4) . ?
C3 C4 1.526(4) . ?
C4 C7 1.505(4) . ?
C4 C10 1.551(4) . ?
C4 C5 1.552(4) . ?
C5 C9 1.538(4) . ?
C5 C6 1.575(4) . ?
C6 C11 1.521(4) . ?
C7 C8 1.523(4) . ?
C8 C9 1.541(4) . ?
C11 C12 1.500(4) . ?
C12 C13 1.399(4) . ?
C12 C17 1.401(4) . ?
C13 C14 1.385(4) . ?
C14 C15 1.380(5) . ?
C15 C16 1.389(5) . ?
C16 C17 1.374(4) . ?
C18 C19 1.397(5) . ?
C18 C23 1.398(4) . ?
C19 C20 1.390(4) . ?
C20 C21 1.390(4) . ?
C21 C22 1.383(5) . ?
C22 C23 1.385(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168346967
