# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_exp_319
_database_code_depnum_ccdc_archive 'CCDC 1824773'
_audit_update_record             
;
2018-02-20 deposited with the CCDC.
2018-03-13 downloaded from the CCDC.
;
_audit_creation_date             2018-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H27 Cl Si2'
_chemical_formula_sum            'C19 H27 Cl Si2'
_chemical_formula_weight         347.03
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H50 Si2 Cl'
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'
Cl Cl 0.1484 0.1585 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.9960(5)
_cell_length_b                   13.4663(7)
_cell_length_c                   15.1960(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.428(5)
_cell_angle_gamma                90
_cell_volume                     2032.67(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3695
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8250
_cell_measurement_theta_min      4.3260
_shelx_estimated_absorpt_T_max   0.915
_shelx_estimated_absorpt_T_min   0.915
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9504
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.541
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  79.00   1.00    8.00    --   14.28  77.00 120.00   91
  2  ω     11.00  39.00   1.00    8.00    --  -18.03  77.00 -60.00   28
  3  ω      4.00  82.00   1.00    8.00    --   14.28  77.00 -90.00   78
  4  ω    -17.00  31.00   1.00    8.00    --  -18.03  77.00-180.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0247730000
_diffrn_orient_matrix_UB_12      0.0172578000
_diffrn_orient_matrix_UB_13      -0.0427334000
_diffrn_orient_matrix_UB_21      -0.0267302000
_diffrn_orient_matrix_UB_22      0.0427361000
_diffrn_orient_matrix_UB_23      0.0190746000
_diffrn_orient_matrix_UB_31      0.0614510000
_diffrn_orient_matrix_UB_32      0.0256433000
_diffrn_orient_matrix_UB_33      -0.0028386000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3186
_reflns_number_total             3996
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3996
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.035
_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/[σ²(Fo²)+(0.0581P)²+0.3901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1206
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3. Others
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(Cl1A)=1-FVAR(1)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(Cl1C)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12)
4.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15D,H15E,H15F), C15C(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C1A(H1AA,H1AB,H1AC), C1(H1A,
 H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
Si1S Si 0.37224(5) 0.67349(5) 0.42401(4) 0.05066(19) Uani 1 1 d . . . . .
C2 C 0.70980(19) 0.60492(16) 0.30030(15) 0.0523(5) Uani 1 1 d . . . . .
Si2S Si 0.23758(6) 0.46050(4) 0.15263(4) 0.04594(18) Uani 1 1 d . . . . .
C3 C 0.62044(19) 0.62855(15) 0.35968(14) 0.0484(5) Uani 1 1 d . . . . .
H3 H 0.652097 0.632169 0.419513 0.058 Uiso 1 1 calc R . . . .
C4 C 0.48352(18) 0.64744(14) 0.33381(12) 0.0404(4) Uani 1 1 d . . . . .
C5 C 0.44053(18) 0.64172(14) 0.24256(12) 0.0407(4) Uani 1 1 d . . . . .
C6 C 0.5320(2) 0.61683(16) 0.18390(13) 0.0532(5) Uani 1 1 d . . . . .
H6 H 0.502348 0.612801 0.123770 0.064 Uiso 1 1 calc R . . . .
C7 C 0.6651(2) 0.59794(17) 0.21203(15) 0.0584(6) Uani 1 1 d . . . . .
H7 H 0.724149 0.580590 0.171464 0.070 Uiso 1 1 calc R . . . .
C8 C 0.30033(18) 0.66785(14) 0.20508(11) 0.0393(4) Uani 1 1 d . . . . .
C9 C 0.2651(2) 0.76783(15) 0.20618(13) 0.0498(5) Uani 1 1 d . . . . .
H9 H 0.326677 0.813452 0.232908 0.060 Uiso 1 1 calc R . . . .
C10 C 0.1414(2) 0.80072(16) 0.16865(14) 0.0542(5) Uani 1 1 d . . . . .
H10 H 0.120357 0.867934 0.169964 0.065 Uiso 1 1 calc R . . . .
C11 C 0.0493(2) 0.73452(17) 0.12934(14) 0.0527(5) Uani 1 1 d . . . . .
C12 C 0.0831(2) 0.63506(16) 0.12799(12) 0.0486(5) Uani 1 1 d . . . . .
H12 H 0.019924 0.590432 0.101505 0.058 Uiso 1 1 calc R . . . .
C13 C 0.20804(18) 0.59845(14) 0.16465(11) 0.0395(4) Uani 1 1 d . . . . .
C14 C 0.0718(3) 0.39638(19) 0.1486(2) 0.0799(8) Uani 1 1 d . . . . .
H14A H 0.029150 0.413922 0.199938 0.120 Uiso 1 1 calc GR . . . .
H14B H 0.085275 0.325824 0.147485 0.120 Uiso 1 1 calc GR . . . .
H14C H 0.015601 0.416357 0.096180 0.120 Uiso 1 1 calc GR . . . .
C15 C 0.3051(3) 0.4383(2) 0.04489(16) 0.0743(7) Uani 1 1 d . . . . .
H15D H 0.244672 0.466154 -0.002242 0.111 Uiso 1 1 calc GR . . . .
H15E H 0.313511 0.368150 0.035617 0.111 Uiso 1 1 calc GR . . . .
H15F H 0.391822 0.469099 0.045793 0.111 Uiso 1 1 calc GR . . . .
C15C C 0.2226(3) 0.5909(3) 0.41359(18) 0.0891(10) Uani 1 1 d . . . . .
H15A H 0.171669 0.600969 0.356903 0.134 Uiso 1 1 calc GR . . . .
H15B H 0.167441 0.606090 0.459619 0.134 Uiso 1 1 calc GR . . . .
H15C H 0.251360 0.522929 0.418865 0.134 Uiso 1 1 calc GR . . . .
C16 C 0.3519(3) 0.40493(18) 0.24370(17) 0.0748(7) Uani 1 1 d . . . . .
H16A H 0.441171 0.430729 0.242182 0.112 Uiso 1 1 calc GR . . . .
H16B H 0.353168 0.334099 0.236703 0.112 Uiso 1 1 calc GR . . . .
H16C H 0.320742 0.421153 0.299447 0.112 Uiso 1 1 calc GR . . . .
C17 C 0.3175(3) 0.8052(2) 0.42696(18) 0.0848(8) Uani 1 1 d . . . . .
H17A H 0.391552 0.847867 0.417516 0.127 Uiso 1 1 calc GR . . . .
H17B H 0.288064 0.819505 0.483617 0.127 Uiso 1 1 calc GR . . . .
H17C H 0.244674 0.816388 0.381272 0.127 Uiso 1 1 calc GR . . . .
C18 C 0.4718(3) 0.6472(2) 0.53208(15) 0.0776(8) Uani 1 1 d . . . . .
H18A H 0.504307 0.580119 0.532547 0.116 Uiso 1 1 calc GR . . . .
H18B H 0.415847 0.655856 0.578896 0.116 Uiso 1 1 calc GR . . . .
H18C H 0.546741 0.692104 0.540681 0.116 Uiso 1 1 calc GR . . . .
C1A C -0.1098(14) 0.7709(12) 0.0858(9) 0.055(3) Uani 0.583(3) 1 d . . P A 1
H1AA H -0.138218 0.731836 0.034191 0.082 Uiso 0.583(3) 1 calc GR . P A 1
H1AB H -0.108450 0.839808 0.069686 0.082 Uiso 0.583(3) 1 calc GR . P A 1
H1AC H -0.171477 0.761328 0.129143 0.082 Uiso 0.583(3) 1 calc GR . P A 1
Cl1C Cl 0.8717(4) 0.5864(3) 0.3371(3) 0.0879(14) Uani 0.583(3) 1 d . . P A 1
C1 C 0.8819(15) 0.5888(11) 0.3343(9) 0.034(3) Uani 0.417(3) 1 d . U P A 2
H1A H 0.922148 0.551425 0.290347 0.050 Uiso 0.417(3) 1 calc GR . P A 2
H1B H 0.893132 0.553675 0.389596 0.050 Uiso 0.417(3) 1 calc GR . P A 2
H1C H 0.924726 0.652577 0.341576 0.050 Uiso 0.417(3) 1 calc GR . P A 2
Cl1A Cl -0.0952(8) 0.7736(6) 0.0833(5) 0.108(2) Uani 0.417(3) 1 d . . P A 2


_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
Si1S C4 1.8922(19) . ?
Si1S C15C 1.856(3) . ?
Si1S C17 1.859(3) . ?
Si1S C18 1.856(2) . ?
C2 C3 1.376(3) . ?
C2 C7 1.369(3) . ?
C2 Cl1C 1.671(5) . ?
C2 C1 1.754(15) . ?
Si2S C13 1.893(2) . ?
Si2S C14 1.863(2) . ?
Si2S C15 1.863(2) . ?
Si2S C16 1.851(2) . ?
C3 C4 1.404(3) . ?
C4 C5 1.407(3) . ?
C5 C6 1.387(3) . ?
C5 C8 1.495(3) . ?
C6 C7 1.375(3) . ?
C8 C9 1.392(3) . ?
C8 C13 1.405(3) . ?
C9 C10 1.376(3) . ?
C10 C11 1.370(3) . ?
C11 C12 1.382(3) . ?
C11 C1A 1.724(14) . ?
C11 Cl1A 1.620(8) . ?
C12 C13 1.399(3) . ?

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
C15C Si1S C4 111.14(10) . . ?
C15C Si1S C17 109.72(15) . . ?
C15C Si1S C18 107.96(14) . . ?
C17 Si1S C4 113.13(11) . . ?
C18 Si1S C4 107.76(10) . . ?
C18 Si1S C17 106.89(13) . . ?
C3 C2 Cl1C 119.4(2) . . ?
C3 C2 C1 121.5(5) . . ?
C7 C2 C3 119.58(19) . . ?
C7 C2 Cl1C 121.0(2) . . ?
C7 C2 C1 118.8(5) . . ?
C14 Si2S C13 108.07(10) . . ?
C14 Si2S C15 107.73(13) . . ?
C15 Si2S C13 108.55(10) . . ?
C16 Si2S C13 114.48(10) . . ?
C16 Si2S C14 108.04(13) . . ?
C16 Si2S C15 109.75(13) . . ?
C2 C3 C4 122.83(19) . . ?
C3 C4 Si1S 117.67(14) . . ?
C3 C4 C5 116.52(17) . . ?
C5 C4 Si1S 125.77(14) . . ?
C4 C5 C8 122.18(16) . . ?
C6 C5 C4 119.73(18) . . ?
C6 C5 C8 117.98(17) . . ?
C7 C6 C5 121.9(2) . . ?
C2 C7 C6 119.38(19) . . ?
C9 C8 C5 116.78(17) . . ?
C9 C8 C13 119.60(17) . . ?
C13 C8 C5 123.48(17) . . ?
C10 C9 C8 121.5(2) . . ?
C11 C10 C9 120.0(2) . . ?
C10 C11 C12 118.90(19) . . ?
C10 C11 C1A 121.9(6) . . ?
C10 C11 Cl1A 120.0(3) . . ?
C12 C11 C1A 119.1(6) . . ?
C12 C11 Cl1A 121.1(3) . . ?
C11 C12 C13 123.0(2) . . ?
C8 C13 Si2S 126.36(14) . . ?
C12 C13 Si2S 116.70(15) . . ?
C12 C13 C8 116.93(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.566
_oxdiff_exptl_absorpt_empirical_full_min 0.544
