# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_170109_s3_zzw
_database_code_depnum_ccdc_archive 'CCDC 1528458'
_audit_update_record             
;
2017-01-19 deposited with the CCDC.
2017-02-22 downloaded from the CCDC.
;
_audit_creation_date             2017-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        170109_s3_zzw
_chemical_formula_moiety         'C16 H25 Br O2 Si'
_chemical_formula_sum            'C16 H25 Br O2 Si'
_chemical_formula_weight         357.36
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3br1si1
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'
Br Br -0.2901 2.4595 '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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_symmetry_space_group_name_H-M_alt 'P 21 21 21'
_cell_length_a                   8.1374(5)
_cell_length_b                   14.2620(9)
_cell_length_c                   16.0081(12)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     1857.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1188
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.9570
_cell_measurement_theta_min      3.5560
_cell_oxdiff_angle_alpha         90.031(9)
_cell_oxdiff_angle_beta          90.014(7)
_cell_oxdiff_angle_gamma         90.163(10)
_cell_oxdiff_length_a            8.1356(8)
_cell_oxdiff_length_b            14.272(2)
_cell_oxdiff_length_c            16.0009(13)
_cell_oxdiff_measurement_reflns_used 1188
_cell_oxdiff_volume              1857.8(3)
_shelx_estimated_absorpt_T_max   0.600
_shelx_estimated_absorpt_T_min   0.503
_exptl_absorpt_coefficient_mu    2.277
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5907
_diffrn_reflns_point_group_measured_fraction_full 0.910
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.918
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -16.00   24.00   0.8000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  150.0000 50

#__ type_ start__ end____ width___ exp.time_
  2 omega    0.00   59.20   0.8000   32.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   57.0000  -30.0000 74

#__ type_ start__ end____ width___ exp.time_
  3 omega  -51.00   -1.40   0.8000   32.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -77.0000    0.0000 62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0172053000
_diffrn_orient_matrix_UB_12      -0.0088736000
_diffrn_orient_matrix_UB_13      0.0427235000
_diffrn_orient_matrix_UB_21      -0.0240282000
_diffrn_orient_matrix_UB_22      0.0463499000
_diffrn_orient_matrix_UB_23      0.0102092000
_diffrn_orient_matrix_UB_31      -0.0820234000
_diffrn_orient_matrix_UB_32      -0.0155895000
_diffrn_orient_matrix_UB_33      0.0059597000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.578
_reflns_Friedel_fraction_full    0.794
_reflns_Friedel_fraction_max     0.773
_reflns_number_gt                1936
_reflns_number_total             3429
_reflns_odcompleteness_completeness 99.46
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 485 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3429
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.031
_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)+(0.0407P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1184
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6), C9(H9)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Br1 Br -0.13233(11) 0.85454(7) 0.21335(7) 0.1171(5) Uani 1 1 d . . . . .
Si1 Si 0.5041(3) 0.43793(16) 0.53182(11) 0.0719(6) Uani 1 1 d . . . . .
O1 O 0.5186(6) 0.6999(3) 0.4304(2) 0.0715(13) Uani 1 1 d . . . . .
H1 H 0.6138 0.6911 0.4452 0.107 Uiso 1 1 calc GR . . . .
O2 O 0.8460(5) 0.6562(3) 0.4957(2) 0.0648(12) Uani 1 1 d . . . . .
H2 H 0.9010 0.7005 0.5126 0.097 Uiso 1 1 calc GR . . . .
C1 C 0.0599(8) 0.7943(5) 0.2538(4) 0.067(2) Uani 1 1 d . . . . .
C2 C 0.0520(9) 0.7420(5) 0.3243(4) 0.070(2) Uani 1 1 d . . . . .
H2A H -0.0475 0.7350 0.3521 0.084 Uiso 1 1 calc R . . . .
C3 C 0.1929(8) 0.6987(5) 0.3550(4) 0.0627(18) Uani 1 1 d . . . . .
H3 H 0.1870 0.6629 0.4034 0.075 Uiso 1 1 calc R . . . .
C4 C 0.3416(8) 0.7086(4) 0.3140(3) 0.0517(16) Uani 1 1 d . . . . .
C5 C 0.3447(9) 0.7612(5) 0.2422(4) 0.0682(19) Uani 1 1 d . . . . .
H5 H 0.4437 0.7685 0.2139 0.082 Uiso 1 1 calc R . . . .
C6 C 0.2032(10) 0.8043(5) 0.2104(5) 0.077(2) Uani 1 1 d . . . . .
H6 H 0.2069 0.8387 0.1610 0.092 Uiso 1 1 calc R . . . .
C7 C 0.4964(8) 0.6649(4) 0.3468(3) 0.0531(15) Uani 1 1 d . . . . .
H7 H 0.5886 0.6867 0.3125 0.064 Uiso 1 1 calc R . . . .
C8 C 0.4956(8) 0.5576(4) 0.3458(3) 0.0475(14) Uani 1 1 d . . . . .
H8 H 0.4006 0.5352 0.3777 0.057 Uiso 1 1 calc R . . . .
C9 C 0.6499(7) 0.5252(4) 0.3881(4) 0.0525(15) Uani 1 1 d . . . . .
H9 H 0.7455 0.5319 0.3569 0.063 Uiso 1 1 calc R . . . .
C10 C 0.6702(7) 0.4882(4) 0.4639(4) 0.0534(16) Uani 1 1 d . . . . .
C11 C 0.8445(7) 0.4884(5) 0.4983(4) 0.0639(18) Uani 1 1 d . . . . .
H11A H 0.8610 0.4340 0.5337 0.077 Uiso 1 1 calc R . . . .
H11B H 0.9228 0.4853 0.4527 0.077 Uiso 1 1 calc R . . . .
C12 C 0.8720(8) 0.5772(4) 0.5485(4) 0.0639(18) Uani 1 1 d . . . . .
H12A H 0.7963 0.5793 0.5953 0.077 Uiso 1 1 calc R . . . .
H12B H 0.9832 0.5783 0.5703 0.077 Uiso 1 1 calc R . . . .
C13 C 0.4821(9) 0.5217(5) 0.2559(3) 0.0711(19) Uani 1 1 d . . . . .
H13A H 0.5738 0.5442 0.2239 0.107 Uiso 1 1 calc GR . . . .
H13B H 0.3817 0.5439 0.2314 0.107 Uiso 1 1 calc GR . . . .
H13C H 0.4825 0.4544 0.2560 0.107 Uiso 1 1 calc GR . . . .
C14 C 0.5777(10) 0.4183(6) 0.6397(4) 0.108(3) Uani 1 1 d . . . . .
H14A H 0.6660 0.3736 0.6391 0.162 Uiso 1 1 calc GR . . . .
H14B H 0.4892 0.3945 0.6733 0.162 Uiso 1 1 calc GR . . . .
H14C H 0.6160 0.4764 0.6628 0.162 Uiso 1 1 calc GR . . . .
C15 C 0.3206(11) 0.5134(10) 0.5420(7) 0.203(7) Uani 1 1 d . . . . .
H15A H 0.3543 0.5769 0.5520 0.305 Uiso 1 1 calc GR . . . .
H15B H 0.2545 0.4918 0.5878 0.305 Uiso 1 1 calc GR . . . .
H15C H 0.2576 0.5106 0.4913 0.305 Uiso 1 1 calc GR . . . .
C16 C 0.4429(14) 0.3233(7) 0.4868(6) 0.176(6) Uani 1 1 d . . . . .
H16A H 0.3874 0.3333 0.4346 0.264 Uiso 1 1 calc GR . . . .
H16B H 0.3706 0.2916 0.5248 0.264 Uiso 1 1 calc GR . . . .
H16C H 0.5390 0.2857 0.4776 0.264 Uiso 1 1 calc GR . . . .


_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
Br1 C1 1.898(6) . ?
Si1 C10 1.877(6) . ?
Si1 C14 1.850(7) . ?
Si1 C15 1.848(9) . ?
Si1 C16 1.855(9) . ?
O1 C7 1.439(6) . ?
O2 C12 1.424(7) . ?
C1 C2 1.354(8) . ?
C1 C6 1.365(9) . ?
C2 C3 1.392(9) . ?
C3 C4 1.384(8) . ?
C4 C5 1.373(8) . ?
C4 C7 1.500(8) . ?
C5 C6 1.401(9) . ?
C7 C8 1.531(7) . ?
C8 C9 1.500(8) . ?
C8 C13 1.532(7) . ?
C9 C10 1.333(8) . ?
C10 C11 1.522(7) . ?
C11 C12 1.517(8) . ?

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
C14 Si1 C10 111.5(3) . . ?
C14 Si1 C16 108.4(5) . . ?
C15 Si1 C10 114.2(4) . . ?
C15 Si1 C14 105.5(5) . . ?
C15 Si1 C16 109.3(6) . . ?
C16 Si1 C10 107.7(4) . . ?
C2 C1 Br1 119.6(6) . . ?
C2 C1 C6 121.5(6) . . ?
C6 C1 Br1 118.9(5) . . ?
C1 C2 C3 120.0(7) . . ?
C4 C3 C2 120.5(6) . . ?
C3 C4 C7 121.7(5) . . ?
C5 C4 C3 117.9(6) . . ?
C5 C4 C7 120.3(6) . . ?
C4 C5 C6 122.0(7) . . ?
C1 C6 C5 118.1(6) . . ?
O1 C7 C4 106.7(5) . . ?
O1 C7 C8 110.9(5) . . ?
C4 C7 C8 114.1(5) . . ?
C7 C8 C13 110.2(5) . . ?
C9 C8 C7 107.4(5) . . ?
C9 C8 C13 112.4(5) . . ?
C10 C9 C8 129.5(6) . . ?
C9 C10 Si1 126.1(5) . . ?
C9 C10 C11 116.4(6) . . ?
C11 C10 Si1 117.5(5) . . ?
C12 C11 C10 109.3(5) . . ?
O2 C12 C11 109.0(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
Br1 C1 C2 C3 -179.1(6) . . . . ?
Br1 C1 C6 C5 178.5(5) . . . . ?
Si1 C10 C11 C12 -87.6(6) . . . . ?
O1 C7 C8 C9 -53.9(7) . . . . ?
O1 C7 C8 C13 -176.7(5) . . . . ?
C1 C2 C3 C4 0.0(11) . . . . ?
C2 C1 C6 C5 -2.0(10) . . . . ?
C2 C3 C4 C5 -0.7(10) . . . . ?
C2 C3 C4 C7 178.3(6) . . . . ?
C3 C4 C5 C6 0.0(9) . . . . ?
C3 C4 C7 O1 -56.7(8) . . . . ?
C3 C4 C7 C8 66.1(7) . . . . ?
C4 C5 C6 C1 1.3(10) . . . . ?
C4 C7 C8 C9 -174.4(5) . . . . ?
C4 C7 C8 C13 62.9(7) . . . . ?
C5 C4 C7 O1 122.3(6) . . . . ?
C5 C4 C7 C8 -114.9(6) . . . . ?
C6 C1 C2 C3 1.4(10) . . . . ?
C7 C4 C5 C6 -179.0(6) . . . . ?
C7 C8 C9 C10 105.4(7) . . . . ?
C8 C9 C10 Si1 16.1(9) . . . . ?
C8 C9 C10 C11 -163.0(6) . . . . ?
C9 C10 C11 C12 91.5(6) . . . . ?
C10 C11 C12 O2 -59.0(7) . . . . ?
C13 C8 C9 C10 -133.3(6) . . . . ?
C14 Si1 C10 C9 -167.5(6) . . . . ?
C14 Si1 C10 C11 11.5(6) . . . . ?
C15 Si1 C10 C9 -48.0(8) . . . . ?
C15 Si1 C10 C11 131.0(6) . . . . ?
C16 Si1 C10 C9 73.6(7) . . . . ?
C16 Si1 C10 C11 -107.4(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc/Hexane'
