# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_904201
_audit_block_doi                 10.5517/ccdc.csd.cc240gd1
_database_code_depnum_ccdc_archive 'CCDC 1966652'
loop_
_audit_author_name
_audit_author_address
'Kenichi Kato'
;Kyoto University
Japan
;
_audit_update_record             
;
2019-11-19 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H22 Cl2 O2 Si'
_chemical_formula_sum            'C15 H22 Cl2 O2 Si'
_chemical_formula_weight         333.31

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'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3456(10)
_cell_length_b                   24.203(4)
_cell_length_c                   8.4795(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.737(4)
_cell_angle_gamma                90
_cell_volume                     1704.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    1592
_cell_measurement_theta_min      31.0
_cell_measurement_theta_max      73.5

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    4.089
_shelx_estimated_absorpt_T_min   0.440
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            11522
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.653
_diffrn_reflns_theta_max         68.422
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3109
_reflns_number_gt                2892
_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0416P)²+0.3431P] 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         3109
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0700
_refine_ls_wR_factor_gt          0.0693
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.001
_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 0.03076(4) 0.41180(2) 0.83179(3) 0.01117(10) Uani 1 1 d . . . . .
Cl1 Cl 0.36250(4) 0.45671(2) 1.41318(4) 0.02914(11) Uani 1 1 d . . . . .
Cl2 Cl 0.39041(4) 0.25058(2) 1.17992(4) 0.02857(11) Uani 1 1 d . . . . .
O1 O 0.02491(10) 0.35934(3) 0.71089(10) 0.01520(18) Uani 1 1 d . . . . .
O2 O -0.14989(10) 0.42903(3) 0.87228(10) 0.01411(18) Uani 1 1 d . . . . .
C6 C -0.25082(15) 0.32831(5) 0.64228(15) 0.0182(3) Uani 1 1 d . . . . .
H1 H -0.2233 0.2981 0.7190 0.022 Uiso 1 1 calc R U . . .
H2 H -0.3204 0.3122 0.5525 0.022 Uiso 1 1 calc R U . . .
C7 C 0.20603(14) 0.42535(5) 1.13281(14) 0.0150(2) Uani 1 1 d . . . . .
H3 H 0.1687 0.4624 1.1243 0.018 Uiso 1 1 calc R U . . .
C8 C 0.11978(15) 0.47588(5) 0.75970(15) 0.0182(3) Uani 1 1 d . . . . .
H4 H 0.2292 0.4683 0.7331 0.027 Uiso 1 1 calc R U . . .
H5 H 0.1235 0.5042 0.8427 0.027 Uiso 1 1 calc R U . . .
H6 H 0.0538 0.4891 0.6652 0.027 Uiso 1 1 calc R U . . .
C9 C -0.28687(14) 0.39325(5) 0.88726(14) 0.0156(2) Uani 1 1 d . . . . .
C10 C 0.36240(15) 0.35507(5) 1.28259(14) 0.0193(3) Uani 1 1 d . . . . .
H7 H 0.4296 0.3441 1.3743 0.023 Uiso 1 1 calc R U . . .
C11 C 0.16089(13) 0.38743(5) 1.01176(14) 0.0132(2) Uani 1 1 d . . . . .
C12 C -0.09431(15) 0.34752(5) 0.57885(14) 0.0162(3) Uani 1 1 d . . . . .
C13 C 0.21894(14) 0.33313(5) 1.02679(14) 0.0157(2) Uani 1 1 d . . . . .
H8 H 0.1908 0.3068 0.9455 0.019 Uiso 1 1 calc R U . . .
C14 C 0.31788(15) 0.31802(5) 1.16127(15) 0.0180(3) Uani 1 1 d . . . . .
C15 C 0.30526(15) 0.40868(5) 1.26518(14) 0.0178(3) Uani 1 1 d . . . . .
C16 C -0.35151(14) 0.37102(5) 0.72338(15) 0.0182(3) Uani 1 1 d . . . . .
H9 H -0.3690 0.4030 0.6511 0.022 Uiso 1 1 calc R U . . .
H10 H -0.4584 0.3544 0.7334 0.022 Uiso 1 1 calc R U . . .
C17 C -0.41460(15) 0.43037(6) 0.94881(17) 0.0236(3) Uani 1 1 d . . . . .
H11 H -0.3736 0.4455 1.0522 0.035 Uiso 1 1 calc R U . . .
H12 H -0.5121 0.4087 0.9599 0.035 Uiso 1 1 calc R U . . .
H13 H -0.4401 0.4607 0.8739 0.035 Uiso 1 1 calc R U . . .
C18 C -0.02340(17) 0.30012(6) 0.48963(16) 0.0241(3) Uani 1 1 d . . . . .
H14 H 0.0799 0.3116 0.4546 0.036 Uiso 1 1 calc R U . . .
H15 H -0.0978 0.2903 0.3971 0.036 Uiso 1 1 calc R U . . .
H16 H -0.0068 0.2680 0.5598 0.036 Uiso 1 1 calc R U . . .
C19 C -0.11985(18) 0.39802(6) 0.47120(15) 0.0234(3) Uani 1 1 d . . . . .
H17 H -0.1556 0.4293 0.5323 0.035 Uiso 1 1 calc R U . . .
H18 H -0.2019 0.3897 0.3836 0.035 Uiso 1 1 calc R U . . .
H19 H -0.0184 0.4075 0.4287 0.035 Uiso 1 1 calc R U . . .
C20 C -0.24090(16) 0.34695(5) 1.00548(15) 0.0215(3) Uani 1 1 d . . . . .
H20 H -0.1555 0.3244 0.9669 0.032 Uiso 1 1 calc R U . . .
H21 H -0.3353 0.3238 1.0170 0.032 Uiso 1 1 calc R U . . .
H22 H -0.2024 0.3630 1.1085 0.032 Uiso 1 1 calc R U . . .


_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 O1 1.6296(8) . ?
Si1 O2 1.6334(9) . ?
Si1 C8 1.8497(12) . ?
Si1 C11 1.8774(12) . ?
Cl1 C15 1.7420(12) . ?
Cl2 C14 1.7426(13) . ?
O1 C12 1.4500(14) . ?
O2 C9 1.4499(14) . ?
C6 C12 1.5336(17) . ?
C6 C16 1.5373(17) . ?
C6 H1 0.9900 . ?
C6 H2 0.9900 . ?
C7 C15 1.3866(18) . ?
C7 C11 1.4002(17) . ?
C7 H3 0.9500 . ?
C8 H4 0.9800 . ?
C8 H5 0.9800 . ?
C8 H6 0.9800 . ?
C9 C17 1.5255(17) . ?
C9 C20 1.5268(17) . ?
C9 C16 1.5367(17) . ?
C10 C15 1.3851(19) . ?
C10 C14 1.3872(19) . ?
C10 H7 0.9500 . ?
C11 C13 1.4022(17) . ?
C12 C18 1.5259(17) . ?
C12 C19 1.5277(17) . ?
C13 C14 1.3884(18) . ?
C13 H8 0.9500 . ?
C16 H9 0.9900 . ?
C16 H10 0.9900 . ?
C17 H11 0.9800 . ?
C17 H12 0.9800 . ?
C17 H13 0.9800 . ?
C18 H14 0.9800 . ?
C18 H15 0.9800 . ?
C18 H16 0.9800 . ?
C19 H17 0.9800 . ?
C19 H18 0.9800 . ?
C19 H19 0.9800 . ?
C20 H20 0.9800 . ?
C20 H21 0.9800 . ?
C20 H22 0.9800 . ?

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
O1 Si1 O2 111.15(4) . . ?
O1 Si1 C8 115.67(5) . . ?
O2 Si1 C8 105.37(5) . . ?
O1 Si1 C11 104.19(5) . . ?
O2 Si1 C11 112.36(5) . . ?
C8 Si1 C11 108.25(5) . . ?
C12 O1 Si1 127.92(7) . . ?
C9 O2 Si1 128.20(7) . . ?
C12 C6 C16 118.41(10) . . ?
C12 C6 H1 107.7 . . ?
C16 C6 H1 107.7 . . ?
C12 C6 H2 107.7 . . ?
C16 C6 H2 107.7 . . ?
H1 C6 H2 107.1 . . ?
C15 C7 C11 119.86(11) . . ?
C15 C7 H3 120.1 . . ?
C11 C7 H3 120.1 . . ?
Si1 C8 H4 109.5 . . ?
Si1 C8 H5 109.5 . . ?
H4 C8 H5 109.5 . . ?
Si1 C8 H6 109.5 . . ?
H4 C8 H6 109.5 . . ?
H5 C8 H6 109.5 . . ?
O2 C9 C17 105.20(10) . . ?
O2 C9 C20 110.32(10) . . ?
C17 C9 C20 110.24(11) . . ?
O2 C9 C16 109.78(9) . . ?
C17 C9 C16 108.75(10) . . ?
C20 C9 C16 112.28(10) . . ?
C15 C10 C14 117.56(11) . . ?
C15 C10 H7 121.2 . . ?
C14 C10 H7 121.2 . . ?
C7 C11 C13 118.85(11) . . ?
C7 C11 Si1 118.78(9) . . ?
C13 C11 Si1 122.34(9) . . ?
O1 C12 C18 105.12(10) . . ?
O1 C12 C19 110.34(10) . . ?
C18 C12 C19 110.07(10) . . ?
O1 C12 C6 109.38(9) . . ?
C18 C12 C6 109.39(10) . . ?
C19 C12 C6 112.29(10) . . ?
C14 C13 C11 119.55(11) . . ?
C14 C13 H8 120.2 . . ?
C11 C13 H8 120.2 . . ?
C10 C14 C13 122.15(11) . . ?
C10 C14 Cl2 118.26(10) . . ?
C13 C14 Cl2 119.60(10) . . ?
C10 C15 C7 122.02(11) . . ?
C10 C15 Cl1 118.79(10) . . ?
C7 C15 Cl1 119.18(10) . . ?
C9 C16 C6 118.80(10) . . ?
C9 C16 H9 107.6 . . ?
C6 C16 H9 107.6 . . ?
C9 C16 H10 107.6 . . ?
C6 C16 H10 107.6 . . ?
H9 C16 H10 107.0 . . ?
C9 C17 H11 109.5 . . ?
C9 C17 H12 109.5 . . ?
H11 C17 H12 109.5 . . ?
C9 C17 H13 109.5 . . ?
H11 C17 H13 109.5 . . ?
H12 C17 H13 109.5 . . ?
C12 C18 H14 109.5 . . ?
C12 C18 H15 109.5 . . ?
H14 C18 H15 109.5 . . ?
C12 C18 H16 109.5 . . ?
H14 C18 H16 109.5 . . ?
H15 C18 H16 109.5 . . ?
C12 C19 H17 109.5 . . ?
C12 C19 H18 109.5 . . ?
H17 C19 H18 109.5 . . ?
C12 C19 H19 109.5 . . ?
H17 C19 H19 109.5 . . ?
H18 C19 H19 109.5 . . ?
C9 C20 H20 109.5 . . ?
C9 C20 H21 109.5 . . ?
H20 C20 H21 109.5 . . ?
C9 C20 H22 109.5 . . ?
H20 C20 H22 109.5 . . ?
H21 C20 H22 109.5 . . ?

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
O2 Si1 O1 C12 37.25(10) . . . . ?
C8 Si1 O1 C12 -82.84(10) . . . . ?
C11 Si1 O1 C12 158.48(9) . . . . ?
O1 Si1 O2 C9 33.98(10) . . . . ?
C8 Si1 O2 C9 160.00(9) . . . . ?
C11 Si1 O2 C9 -82.33(10) . . . . ?
Si1 O2 C9 C17 172.14(8) . . . . ?
Si1 O2 C9 C20 53.26(13) . . . . ?
Si1 O2 C9 C16 -71.00(12) . . . . ?
C15 C7 C11 C13 -0.60(17) . . . . ?
C15 C7 C11 Si1 -178.45(9) . . . . ?
O1 Si1 C11 C7 172.68(9) . . . . ?
O2 Si1 C11 C7 -66.89(10) . . . . ?
C8 Si1 C11 C7 49.05(11) . . . . ?
O1 Si1 C11 C13 -5.09(11) . . . . ?
O2 Si1 C11 C13 115.34(10) . . . . ?
C8 Si1 C11 C13 -128.72(10) . . . . ?
Si1 O1 C12 C18 169.44(8) . . . . ?
Si1 O1 C12 C19 50.81(13) . . . . ?
Si1 O1 C12 C6 -73.19(12) . . . . ?
C16 C6 C12 O1 70.84(13) . . . . ?
C16 C6 C12 C18 -174.51(10) . . . . ?
C16 C6 C12 C19 -52.00(14) . . . . ?
C7 C11 C13 C14 0.69(17) . . . . ?
Si1 C11 C13 C14 178.46(9) . . . . ?
C15 C10 C14 C13 -0.42(18) . . . . ?
C15 C10 C14 Cl2 179.28(10) . . . . ?
C11 C13 C14 C10 -0.18(18) . . . . ?
C11 C13 C14 Cl2 -179.88(9) . . . . ?
C14 C10 C15 C7 0.52(19) . . . . ?
C14 C10 C15 Cl1 -178.56(9) . . . . ?
C11 C7 C15 C10 -0.01(19) . . . . ?
C11 C7 C15 Cl1 179.07(9) . . . . ?
O2 C9 C16 C6 70.76(13) . . . . ?
C17 C9 C16 C6 -174.63(11) . . . . ?
C20 C9 C16 C6 -52.35(14) . . . . ?
C12 C6 C16 C9 -70.87(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H3 O2 0.95 2.63 3.5552(15) 164.0 3_567
C16 H10 Cl2 0.99 2.85 3.6439(13) 137.4 4_465

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.052


_exptl_crystal_recrystallization_method 'From the Melt'
