# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_mo211211a_pl
_database_code_depnum_ccdc_archive 'CCDC 2131880'
loop_
_audit_author_name
_audit_author_address
'kunlong song'
;hangzhounormaluniversity
China
;
_audit_update_record             
;
2021-12-31 deposited with the CCDC.	2022-05-25 downloaded from the CCDC.
;
_audit_creation_date             2021-12-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            
(E)-(2,4-bis(4-bromophenyl)but-1-en-3-yn-1-yl)trimethylsilane
_chemical_name_systematic        
(E)-(2,4-bis(4-bromophenyl)but-1-en-3-yn-1-yl)trimethylsilane
_chemical_formula_moiety         'C19 H18 Br2 Si'
_chemical_formula_sum            'C19 H18 Br2 Si'
_chemical_formula_weight         434.24
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'
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'

_cell_length_a                   6.1450(14)
_cell_length_b                   15.369(4)
_cell_length_c                   20.888(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1972.7(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2352
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      17.753
_cell_measurement_theta_min      2.358
_shelx_estimated_absorpt_T_max   0.635
_shelx_estimated_absorpt_T_min   0.574
_exptl_absorpt_coefficient_mu    4.165
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0803 before and 0.0674 after correction.
The Ratio of minimum to maximum transmission is 0.7157.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1323
_diffrn_reflns_av_unetI/netI     0.1309
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            21792
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.526
_diffrn_reflns_theta_min         1.645
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                2463
_reflns_number_total             5645
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.011(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         5645
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1665
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      0.962
_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)+(0.0378P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1363
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.011(18)
 -0.011(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16)
3.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 1.4693(2) 0.01641(6) 0.57281(4) 0.1047(4) Uani 1 1 d . . . . .
Br2 Br 0.34212(16) 0.62603(6) 0.29350(5) 0.0978(4) Uani 1 1 d . . . . .
Si1 Si 0.9410(3) 0.33543(13) 0.11414(9) 0.0563(5) Uani 1 1 d . . . . .
C1 C 1.0391(11) 0.2982(4) 0.1946(3) 0.0507(16) Uani 1 1 d . . . . .
H1 H 1.1523 0.2581 0.1935 0.061 Uiso 1 1 calc R U . . .
C2 C 0.9722(11) 0.3202(4) 0.2529(3) 0.0457(15) Uani 1 1 d . . . . .
C3 C 1.0492(12) 0.2754(4) 0.3088(3) 0.0519(16) Uani 1 1 d . . . . .
C4 C 1.1126(12) 0.2378(4) 0.3556(3) 0.0577(19) Uani 1 1 d . . . . .
C5 C 1.2007(12) 0.1894(4) 0.4083(3) 0.0497(17) Uani 1 1 d . . . . .
C6 C 1.0842(12) 0.1799(4) 0.4653(3) 0.0575(18) Uani 1 1 d . . . . .
H6 H 0.9511 0.2079 0.4703 0.069 Uiso 1 1 calc R U . . .
C7 C 1.1662(15) 0.1290(5) 0.5142(3) 0.066(2) Uani 1 1 d . . . . .
H7 H 1.0873 0.1222 0.5519 0.079 Uiso 1 1 calc R U . . .
C8 C 1.3602(15) 0.0891(4) 0.5075(3) 0.0584(19) Uani 1 1 d . . . . .
C9 C 1.4798(13) 0.0986(4) 0.4523(4) 0.063(2) Uani 1 1 d . . . . .
H9 H 1.6136 0.0709 0.4482 0.076 Uiso 1 1 calc R U . . .
C10 C 1.3997(12) 0.1498(4) 0.4028(3) 0.060(2) Uani 1 1 d . . . . .
H10 H 1.4814 0.1572 0.3657 0.072 Uiso 1 1 calc R U . . .
C11 C 0.8174(11) 0.3925(4) 0.2647(3) 0.0437(15) Uani 1 1 d . . . . .
C12 C 0.8737(12) 0.4766(4) 0.2469(3) 0.0523(17) Uani 1 1 d . . . . .
H12 H 1.0092 0.4866 0.2284 0.063 Uiso 1 1 calc R U . . .
C13 C 0.7351(13) 0.5450(4) 0.2558(3) 0.0582(19) Uani 1 1 d . . . . .
H13 H 0.7769 0.6008 0.2438 0.070 Uiso 1 1 calc R U . . .
C14 C 0.5331(12) 0.5311(4) 0.2827(3) 0.0584(18) Uani 1 1 d . . . . .
C15 C 0.4751(13) 0.4478(4) 0.3019(3) 0.0647(19) Uani 1 1 d . . . . .
H15 H 0.3406 0.4383 0.3210 0.078 Uiso 1 1 calc R U . . .
C16 C 0.6148(11) 0.3797(4) 0.2927(3) 0.0542(17) Uani 1 1 d . . . . .
H16 H 0.5737 0.3241 0.3054 0.065 Uiso 1 1 calc R U . . .
C17 C 1.008(2) 0.2456(6) 0.0603(4) 0.101(3) Uani 1 1 d . . . . .
H17A H 0.9240 0.1954 0.0716 0.152 Uiso 1 1 calc R U . . .
H17B H 1.1605 0.2323 0.0639 0.152 Uiso 1 1 calc R U . . .
H17C H 0.9759 0.2622 0.0170 0.152 Uiso 1 1 calc R U . . .
C18 C 1.0774(13) 0.4375(6) 0.0871(4) 0.093(3) Uani 1 1 d . . . . .
H18A H 1.0432 0.4480 0.0429 0.140 Uiso 1 1 calc R U . . .
H18B H 1.2320 0.4316 0.0919 0.140 Uiso 1 1 calc R U . . .
H18C H 1.0270 0.4855 0.1126 0.140 Uiso 1 1 calc R U . . .
C19 C 0.6448(12) 0.3538(5) 0.1136(4) 0.072(2) Uani 1 1 d . . . . .
H19A H 0.5722 0.3035 0.1305 0.108 Uiso 1 1 calc R U . . .
H19B H 0.5970 0.3640 0.0704 0.108 Uiso 1 1 calc R U . . .
H19C H 0.6109 0.4036 0.1395 0.108 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
Br1 C8 1.886(7) . ?
Br2 C14 1.886(7) . ?
Si1 C1 1.874(7) . ?
Si1 C17 1.828(8) . ?
Si1 C18 1.866(8) . ?
Si1 C19 1.842(8) . ?
C1 H1 0.9300 . ?
C1 C2 1.331(8) . ?
C2 C3 1.434(9) . ?
C2 C11 1.483(8) . ?
C3 C4 1.202(9) . ?
C4 C5 1.435(9) . ?
C5 C6 1.396(9) . ?
C5 C10 1.371(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.382(9) . ?
C7 H7 0.9300 . ?
C7 C8 1.348(11) . ?
C8 C9 1.375(10) . ?
C9 H9 0.9300 . ?
C9 C10 1.390(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(8) . ?
C11 C16 1.390(9) . ?
C12 H12 0.9300 . ?
C12 C13 1.365(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(10) . ?
C14 C15 1.388(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.367(9) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
C17 Si1 C1 104.4(4) . . ?
C17 Si1 C18 110.3(4) . . ?
C17 Si1 C19 109.6(5) . . ?
C18 Si1 C1 112.5(4) . . ?
C19 Si1 C1 111.7(3) . . ?
C19 Si1 C18 108.2(4) . . ?
Si1 C1 H1 114.9 . . ?
C2 C1 Si1 130.2(5) . . ?
C2 C1 H1 114.9 . . ?
C1 C2 C3 121.4(6) . . ?
C1 C2 C11 122.6(5) . . ?
C3 C2 C11 115.9(5) . . ?
C4 C3 C2 179.7(8) . . ?
C3 C4 C5 175.5(8) . . ?
C6 C5 C4 121.0(6) . . ?
C10 C5 C4 120.1(6) . . ?
C10 C5 C6 118.9(6) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.2(7) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(7) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 Br1 120.6(6) . . ?
C7 C8 C9 120.8(6) . . ?
C9 C8 Br1 118.6(6) . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(7) . . ?
C10 C9 H9 120.2 . . ?
C5 C10 C9 120.3(7) . . ?
C5 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C2 119.6(6) . . ?
C12 C11 C16 117.9(6) . . ?
C16 C11 C2 122.6(5) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.6(6) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.9(6) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 Br2 119.3(5) . . ?
C13 C14 C15 119.4(6) . . ?
C15 C14 Br2 121.3(6) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.3(7) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 120.9(6) . . ?
C15 C16 H16 119.5 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Si1 C19 H19A 109.5 . . ?
Si1 C19 H19B 109.5 . . ?
Si1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
Br1 C8 C9 C10 178.1(5) . . . . ?
Br2 C14 C15 C16 179.1(5) . . . . ?
Si1 C1 C2 C3 171.5(5) . . . . ?
Si1 C1 C2 C11 -9.4(10) . . . . ?
C1 C2 C11 C12 -61.2(9) . . . . ?
C1 C2 C11 C16 118.3(7) . . . . ?
C2 C11 C12 C13 179.0(6) . . . . ?
C2 C11 C16 C15 -179.0(6) . . . . ?
C3 C2 C11 C12 117.9(6) . . . . ?
C3 C2 C11 C16 -62.5(8) . . . . ?
C4 C5 C6 C7 176.3(7) . . . . ?
C4 C5 C10 C9 -176.2(6) . . . . ?
C5 C6 C7 C8 0.8(11) . . . . ?
C6 C5 C10 C9 2.2(10) . . . . ?
C6 C7 C8 Br1 -177.9(5) . . . . ?
C6 C7 C8 C9 0.3(11) . . . . ?
C7 C8 C9 C10 -0.1(11) . . . . ?
C8 C9 C10 C5 -1.2(10) . . . . ?
C10 C5 C6 C7 -2.0(10) . . . . ?
C11 C12 C13 C14 -0.5(10) . . . . ?
C12 C11 C16 C15 0.6(9) . . . . ?
C12 C13 C14 Br2 -179.1(5) . . . . ?
C12 C13 C14 C15 1.6(10) . . . . ?
C13 C14 C15 C16 -1.7(10) . . . . ?
C14 C15 C16 C11 0.6(10) . . . . ?
C16 C11 C12 C13 -0.6(10) . . . . ?
C17 Si1 C1 C2 -154.0(7) . . . . ?
C18 Si1 C1 C2 86.4(7) . . . . ?
C19 Si1 C1 C2 -35.6(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.011(18)
2 -0.011(18)

####################################################################### 
# 
# 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_mo211215a
_database_code_depnum_ccdc_archive 'CCDC 2141725'
loop_
_audit_author_name
_audit_author_address
'kunlong song'
;hangzhounormaluniversity
China
;
_audit_update_record             
;
2022-01-13 deposited with the CCDC.	2022-05-25 downloaded from the CCDC.
;
_audit_creation_date             2021-12-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 Br2 Si'
_chemical_formula_sum            'C19 H18 Br2 Si'
_chemical_formula_weight         434.24
_chemical_melting_point          ?
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'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.886(8)
_cell_length_b                   6.1944(12)
_cell_length_c                   22.938(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.585(9)
_cell_angle_gamma                90
_cell_volume                     3816.4(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1617
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      18.682
_cell_measurement_theta_min      3.034
_shelx_estimated_absorpt_T_max   0.626
_shelx_estimated_absorpt_T_min   0.564
_exptl_absorpt_coefficient_mu    4.306
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0624 before and 0.0393 after correction.
The Ratio of minimum to maximum transmission is 0.8906.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_unetI/netI     0.1131
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17550
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.526
_diffrn_reflns_theta_min         1.910
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2007
_reflns_number_total             5243
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         5243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1907
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      0.973
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+0.0385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1268
_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.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.85235(2) 0.05059(9) 0.35862(3) 0.0764(2) Uani 1 1 d . . . . .
Br2 Br 0.50585(2) 1.43724(12) 0.07861(3) 0.1030(3) Uani 1 1 d . . . . .
Si1 Si 0.63236(5) 0.8520(2) 0.45697(6) 0.0598(4) Uani 1 1 d . . . . .
C1 C 0.60027(17) 0.9721(7) 0.3773(2) 0.0551(12) Uani 1 1 d . . . . .
H1 H 0.5738 1.0642 0.3733 0.066 Uiso 1 1 calc R U . . .
C2 C 0.61037(16) 0.9430(7) 0.3251(2) 0.0523(11) Uani 1 1 d . . . . .
C3 C 0.64807(16) 0.7888(7) 0.32471(19) 0.0486(11) Uani 1 1 d . . . . .
C4 C 0.68006(17) 0.6658(8) 0.3256(2) 0.0526(12) Uani 1 1 d . . . . .
C5 C 0.71920(15) 0.5164(7) 0.3297(2) 0.0471(11) Uani 1 1 d . . . . .
C6 C 0.71944(17) 0.3090(7) 0.3533(2) 0.0573(12) Uani 1 1 d . . . . .
H6 H 0.6928 0.2630 0.3638 0.069 Uiso 1 1 calc R U . . .
C7 C 0.75867(17) 0.1724(7) 0.3613(2) 0.0564(12) Uani 1 1 d . . . . .
H7 H 0.7584 0.0340 0.3768 0.068 Uiso 1 1 calc R U . . .
C8 C 0.79804(16) 0.2379(7) 0.3465(2) 0.0511(11) Uani 1 1 d . . . . .
C9 C 0.79857(16) 0.4426(7) 0.3225(2) 0.0545(12) Uani 1 1 d . . . . .
H9 H 0.8253 0.4866 0.3120 0.065 Uiso 1 1 calc R U . . .
C10 C 0.75942(17) 0.5802(7) 0.3143(2) 0.0535(12) Uani 1 1 d . . . . .
H10 H 0.7598 0.7178 0.2983 0.064 Uiso 1 1 calc R U . . .
C11 C 0.58543(15) 1.0605(7) 0.2652(2) 0.0478(11) Uani 1 1 d . . . . .
C12 C 0.57905(17) 0.9720(8) 0.2084(2) 0.0590(13) Uani 1 1 d . . . . .
H12 H 0.5915 0.8342 0.2071 0.071 Uiso 1 1 calc R U . . .
C13 C 0.55464(19) 1.0798(9) 0.1520(2) 0.0704(15) Uani 1 1 d . . . . .
H13 H 0.5501 1.0145 0.1138 0.084 Uiso 1 1 calc R U . . .
C14 C 0.53771(16) 1.2818(9) 0.1544(2) 0.0607(13) Uani 1 1 d . . . . .
C15 C 0.54356(18) 1.3812(8) 0.2095(3) 0.0694(15) Uani 1 1 d . . . . .
H15 H 0.5317 1.5206 0.2099 0.083 Uiso 1 1 calc R U . . .
C16 C 0.56785(16) 1.2697(8) 0.2657(2) 0.0624(13) Uani 1 1 d . . . . .
H16 H 0.5723 1.3360 0.3038 0.075 Uiso 1 1 calc R U . . .
C17 C 0.5957(2) 0.9356(8) 0.5052(2) 0.0828(17) Uani 1 1 d . . . . .
H17A H 0.5942 1.0903 0.5062 0.124 Uiso 1 1 calc R U . . .
H17B H 0.6115 0.8816 0.5471 0.124 Uiso 1 1 calc R U . . .
H17C H 0.5626 0.8780 0.4872 0.124 Uiso 1 1 calc R U . . .
C18 C 0.6362(2) 0.5545(7) 0.4544(3) 0.0809(16) Uani 1 1 d . . . . .
H18A H 0.6040 0.4968 0.4300 0.121 Uiso 1 1 calc R U . . .
H18B H 0.6469 0.4979 0.4963 0.121 Uiso 1 1 calc R U . . .
H18C H 0.6596 0.5142 0.4356 0.121 Uiso 1 1 calc R U . . .
C19 C 0.69635(19) 0.9643(8) 0.4900(3) 0.0853(17) Uani 1 1 d . . . . .
H19A H 0.7135 0.9329 0.4622 0.128 Uiso 1 1 calc R U . . .
H19B H 0.7140 0.9002 0.5302 0.128 Uiso 1 1 calc R U . . .
H19C H 0.6947 1.1178 0.4946 0.128 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
Br1 C8 1.888(4) . ?
Br2 C14 1.902(5) . ?
Si1 C1 1.872(5) . ?
Si1 C17 1.864(5) . ?
Si1 C18 1.848(5) . ?
Si1 C19 1.856(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.344(6) . ?
C2 C3 1.451(6) . ?
C2 C11 1.487(6) . ?
C3 C4 1.192(6) . ?
C4 C5 1.437(6) . ?
C5 C6 1.394(6) . ?
C5 C10 1.390(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.372(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.362(6) . ?
C8 C9 1.385(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.373(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.363(6) . ?
C11 C16 1.393(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.394(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.352(7) . ?
C14 C15 1.360(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.402(6) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
C17 Si1 C1 106.5(2) . . ?
C18 Si1 C1 112.3(2) . . ?
C18 Si1 C17 110.5(2) . . ?
C18 Si1 C19 108.9(3) . . ?
C19 Si1 C1 108.1(2) . . ?
C19 Si1 C17 110.6(3) . . ?
Si1 C1 H1 115.7 . . ?
C2 C1 Si1 128.6(3) . . ?
C2 C1 H1 115.7 . . ?
C1 C2 C3 120.2(4) . . ?
C1 C2 C11 124.6(4) . . ?
C3 C2 C11 115.2(4) . . ?
C4 C3 C2 178.1(5) . . ?
C3 C4 C5 177.4(5) . . ?
C6 C5 C4 120.7(4) . . ?
C10 C5 C4 120.8(4) . . ?
C10 C5 C6 118.4(4) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.4(4) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.5(4) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 Br1 120.3(3) . . ?
C7 C8 C9 120.3(4) . . ?
C9 C8 Br1 119.4(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C5 C10 H10 119.6 . . ?
C9 C10 C5 120.8(4) . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C2 122.5(4) . . ?
C12 C11 C16 117.5(4) . . ?
C16 C11 C2 120.1(4) . . ?
C11 C12 H12 118.7 . . ?
C11 C12 C13 122.6(5) . . ?
C13 C12 H12 118.7 . . ?
C12 C13 H13 120.9 . . ?
C14 C13 C12 118.3(5) . . ?
C14 C13 H13 120.9 . . ?
C13 C14 Br2 119.5(4) . . ?
C13 C14 C15 122.2(5) . . ?
C15 C14 Br2 118.3(4) . . ?
C14 C15 H15 120.6 . . ?
C14 C15 C16 118.7(5) . . ?
C16 C15 H15 120.6 . . ?
C11 C16 C15 120.7(5) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Si1 C19 H19A 109.5 . . ?
Si1 C19 H19B 109.5 . . ?
Si1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
Br1 C8 C9 C10 -179.3(3) . . . . ?
Br2 C14 C15 C16 -178.8(3) . . . . ?
Si1 C1 C2 C3 5.2(7) . . . . ?
Si1 C1 C2 C11 -174.5(4) . . . . ?
C1 C2 C11 C12 -150.4(5) . . . . ?
C1 C2 C11 C16 30.1(7) . . . . ?
C2 C11 C12 C13 178.4(4) . . . . ?
C2 C11 C16 C15 -179.0(4) . . . . ?
C3 C2 C11 C12 29.9(6) . . . . ?
C3 C2 C11 C16 -149.6(4) . . . . ?
C4 C5 C6 C7 -175.3(4) . . . . ?
C4 C5 C10 C9 175.2(4) . . . . ?
C5 C6 C7 C8 0.4(7) . . . . ?
C6 C5 C10 C9 -0.3(7) . . . . ?
C6 C7 C8 Br1 179.1(3) . . . . ?
C6 C7 C8 C9 -0.8(7) . . . . ?
C7 C8 C9 C10 0.7(7) . . . . ?
C8 C9 C10 C5 -0.1(7) . . . . ?
C10 C5 C6 C7 0.2(7) . . . . ?
C11 C12 C13 C14 1.4(7) . . . . ?
C12 C11 C16 C15 1.4(7) . . . . ?
C12 C13 C14 Br2 178.3(3) . . . . ?
C12 C13 C14 C15 -0.3(7) . . . . ?
C13 C14 C15 C16 -0.2(7) . . . . ?
C14 C15 C16 C11 -0.3(7) . . . . ?
C16 C11 C12 C13 -2.0(7) . . . . ?
C17 Si1 C1 C2 -174.1(4) . . . . ?
C18 Si1 C1 C2 -53.1(5) . . . . ?
C19 Si1 C1 C2 67.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
