# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_210617_lxn_3_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2gqdvg
_database_code_depnum_ccdc_archive 'CCDC 2285656'
loop_
_audit_author_name
_audit_author_address
'Jian Zhang'
;Hangzhou Normal University
China
;
_audit_update_record             
;
2023-07-29 deposited with the CCDC.	2023-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H16 O Si'
_chemical_formula_weight         216.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   8.6562(3)
_cell_length_b                   7.0369(2)
_cell_length_c                   9.8957(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.7960(10)
_cell_angle_gamma                90
_cell_volume                     597.20(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_F_000             232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.168
_shelx_estimated_absorpt_T_min   0.922
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11768
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.375
_diffrn_reflns_theta_max         27.116
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1422
_reflns_number_gt                1332
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+0.2198P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1422
_refine_ls_number_parameters     88
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.84220(5) 0.250000 0.20898(4) 0.02367(16) Uani 1 2 d S T P . .
O1 O 0.33177(17) 0.250000 -0.03621(15) 0.0486(4) Uani 1 2 d S T P . .
C1 C 0.7112(2) 0.250000 0.51855(17) 0.0268(4) Uani 1 2 d S T P . .
H1 H 0.820673 0.250000 0.516685 0.032 Uiso 1 2 calc R U P . .
C2 C 0.6508(2) 0.250000 0.64207(18) 0.0320(4) Uani 1 2 d S T P . .
H2 H 0.720008 0.250000 0.725244 0.038 Uiso 1 2 calc R U P . .
C3 C 0.4904(3) 0.250000 0.64547(19) 0.0350(4) Uani 1 2 d S T P . .
H3 H 0.451512 0.250000 0.730730 0.042 Uiso 1 2 calc R U P . .
C4 C 0.3869(2) 0.250000 0.52499(19) 0.0316(4) Uani 1 2 d S T P . .
H4 H 0.277487 0.250000 0.527171 0.038 Uiso 1 2 calc R U P . .
C5 C 0.4460(2) 0.250000 0.40203(17) 0.0245(3) Uani 1 2 d S T P . .
C6 C 0.60730(19) 0.250000 0.39746(16) 0.0223(3) Uani 1 2 d S T P . .
C7 C 0.63665(19) 0.250000 0.25352(16) 0.0227(3) Uani 1 2 d S T P . .
C8 C 0.49404(19) 0.250000 0.17499(17) 0.0244(3) Uani 1 2 d S T P . .
C9 C 0.36198(19) 0.250000 0.25954(18) 0.0269(4) Uani 1 2 d S T P . .
H9A H 0.296109 0.364664 0.241655 0.032 Uiso 0.5 1 calc R U P . .
H9B H 0.296109 0.135336 0.241654 0.032 Uiso 0.5 1 calc R U P . .
C10 C 0.93684(15) 0.4709(2) 0.28456(15) 0.0366(3) Uani 1 1 d . . . . .
H10A H 0.929600 0.474295 0.382506 0.055 Uiso 1 1 calc R U . . .
H10B H 1.046754 0.472258 0.270540 0.055 Uiso 1 1 calc R U . . .
H10C H 0.883875 0.582171 0.240339 0.055 Uiso 1 1 calc R U . . .
C11 C 0.8589(2) 0.250000 0.0231(2) 0.0401(5) Uani 1 2 d S T P . .
H11A H 0.809917 0.135052 -0.019138 0.060 Uiso 0.5 1 calc R U P A -1
H11B H 0.806350 0.362430 -0.019799 0.060 Uiso 0.5 1 calc R U P A -1
H11C H 0.969229 0.252518 0.010402 0.060 Uiso 0.5 1 calc R U P A -1
C12 C 0.4624(2) 0.250000 0.02707(18) 0.0333(4) Uani 1 2 d S T P . .
H12 H 0.548536 0.250000 -0.023049 0.040 Uiso 1 2 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C11 1.865(2) . ?
Si1 C10 1.8656(14) . ?
Si1 C10 1.8656(14) 4_565 ?
Si1 C7 1.8902(17) . ?
O1 C12 1.216(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.397(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.393(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(2) . ?
C5 C9 1.496(2) . ?
C6 C7 1.480(2) . ?
C7 C8 1.367(2) . ?
C8 C12 1.452(2) . ?
C8 C9 1.505(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 0.9500 . ?

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
C11 Si1 C10 107.87(6) . . ?
C11 Si1 C10 107.87(6) . 4_565 ?
C10 Si1 C10 112.86(9) . 4_565 ?
C11 Si1 C7 115.56(8) . . ?
C10 Si1 C7 106.41(5) . . ?
C10 Si1 C7 106.41(5) 4_565 . ?
C2 C1 C6 118.53(17) . . ?
C2 C1 H1 120.7 . . ?
C6 C1 H1 120.7 . . ?
C3 C2 C1 121.00(17) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 120.51(17) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 118.81(17) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.14(16) . . ?
C4 C5 C9 129.71(16) . . ?
C6 C5 C9 109.16(14) . . ?
C1 C6 C5 120.01(16) . . ?
C1 C6 C7 130.58(15) . . ?
C5 C6 C7 109.42(14) . . ?
C8 C7 C6 106.70(14) . . ?
C8 C7 Si1 132.35(13) . . ?
C6 C7 Si1 120.95(12) . . ?
C7 C8 C12 127.27(16) . . ?
C7 C8 C9 112.30(15) . . ?
C12 C8 C9 120.43(15) . . ?
C5 C9 C8 102.42(13) . . ?
C5 C9 H9A 111.3 . . ?
C8 C9 H9A 111.3 . . ?
C5 C9 H9B 111.3 . . ?
C8 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
Si1 C10 H10A 109.5 . . ?
Si1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
Si1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Si1 C11 H11A 109.5 . . ?
Si1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Si1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 C8 123.66(18) . . ?
O1 C12 H12 118.2 . . ?
C8 C12 H12 118.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.000(1) . . . . ?
C1 C2 C3 C4 0.000(1) . . . . ?
C2 C3 C4 C5 0.000(1) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
C3 C4 C5 C9 180.000(0) . . . . ?
C2 C1 C6 C5 0.000(0) . . . . ?
C2 C1 C6 C7 180.000(0) . . . . ?
C4 C5 C6 C1 0.000(0) . . . . ?
C9 C5 C6 C1 180.000(0) . . . . ?
C4 C5 C6 C7 180.000(0) . . . . ?
C9 C5 C6 C7 0.000(0) . . . . ?
C1 C6 C7 C8 180.000(0) . . . . ?
C5 C6 C7 C8 0.000(0) . . . . ?
C1 C6 C7 Si1 0.000(0) . . . . ?
C5 C6 C7 Si1 180.000(0) . . . . ?
C11 Si1 C7 C8 0.000(0) . . . . ?
C10 Si1 C7 C8 119.71(5) . . . . ?
C10 Si1 C7 C8 -119.71(5) 4_565 . . . ?
C11 Si1 C7 C6 180.000(0) . . . . ?
C10 Si1 C7 C6 -60.29(5) . . . . ?
C10 Si1 C7 C6 60.29(5) 4_565 . . . ?
C6 C7 C8 C12 180.000(0) . . . . ?
Si1 C7 C8 C12 0.000(0) . . . . ?
C6 C7 C8 C9 0.000(0) . . . . ?
Si1 C7 C8 C9 180.000(0) . . . . ?
C4 C5 C9 C8 180.000(0) . . . . ?
C6 C5 C9 C8 0.000(0) . . . . ?
C7 C8 C9 C5 0.000(0) . . . . ?
C12 C8 C9 C5 180.000(0) . . . . ?
C7 C8 C12 O1 180.000(0) . . . . ?
C9 C8 C12 O1 0.000(0) . . . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.066

