# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_cx0864_0m
_database_code_depnum_ccdc_archive 'CCDC 1539450'
_audit_update_record             
;
2017-03-21 deposited with the CCDC.
2017-06-07 downloaded from the CCDC.
;
_audit_creation_date             2016-10-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H44'
_chemical_formula_sum            'C36 H44'
_chemical_formula_weight         476.71
_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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2828(4)
_cell_length_b                   8.9132(4)
_cell_length_c                   9.1524(4)
_cell_angle_alpha                88.129(2)
_cell_angle_beta                 79.474(2)
_cell_angle_gamma                86.662(2)
_cell_volume                     663.02(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.775
_cell_measurement_theta_min      2.264
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1614 before and 0.0736 after correction.
The Ratio of minimum to maximum transmission is 0.8221.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.686
_exptl_crystal_size_mid          0.481
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14580
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.775
_diffrn_reflns_theta_max         25.775
_diffrn_reflns_theta_min         2.289
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'QuazarTM optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   microsource
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2419
_reflns_number_total             2529
_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 V8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2529
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.075
_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)+(0.0677P)²+0.3516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1367
_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
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C15(H15A,H15B), C16(H16A,H16B),
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C11(H11), C13(H13)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.72427(18) 0.58712(15) 1.03367(16) 0.0212(3) Uani 1 1 d . . . . .
H1A H 0.7742 0.5218 0.9516 0.032 Uiso 1 1 calc GR . . . .
H1B H 0.6696 0.5258 1.1169 0.032 Uiso 1 1 calc GR . . . .
H1C H 0.8100 0.6424 1.0660 0.032 Uiso 1 1 calc GR . . . .
C2 C 0.59850(17) 0.69818(15) 0.98158(15) 0.0196(3) Uani 1 1 d . . . . .
H2A H 0.5193 0.6422 0.9384 0.024 Uiso 1 1 calc R . . . .
H2B H 0.5364 0.7534 1.0681 0.024 Uiso 1 1 calc R . . . .
C3 C 0.67970(16) 0.81027(15) 0.86603(15) 0.0170(3) Uani 1 1 d . . . . .
H3A H 0.7537 0.7541 0.7866 0.020 Uiso 1 1 calc R . . . .
H3B H 0.7483 0.8740 0.9136 0.020 Uiso 1 1 calc R . . . .
C4 C 0.55840(16) 0.91251(14) 0.79473(14) 0.0152(3) Uani 1 1 d . . . . .
H4A H 0.4706 0.9534 0.8739 0.018 Uiso 1 1 calc R . . . .
H4B H 0.6170 0.9983 0.7429 0.018 Uiso 1 1 calc R . . . .
C5 C 0.48112(16) 0.83071(14) 0.68526(15) 0.0137(3) Uani 1 1 d . . . . .
C6 C 0.32722(16) 0.77529(14) 0.72950(14) 0.0138(3) Uani 1 1 d . . . . .
H6 H 0.2703 0.7943 0.8276 0.017 Uiso 1 1 calc R . . . .
C7 C 0.25084(16) 0.69196(14) 0.63588(14) 0.0137(3) Uani 1 1 d . . . . .
C8 C 0.08971(15) 0.63698(14) 0.68709(14) 0.0139(3) Uani 1 1 d . . . . .
H8 H 0.0309 0.6551 0.7847 0.017 Uiso 1 1 calc R . . . .
C9 C 0.02637(15) 0.55809(14) 0.58894(15) 0.0138(3) Uani 1 1 d . . . . .
C10 C 0.11503(16) 0.52704(14) 0.44119(15) 0.0139(3) Uani 1 1 d . . . . .
C11 C 0.26736(16) 0.57546(14) 0.38942(14) 0.0144(3) Uani 1 1 d . . . . .
H11 H 0.3247 0.5531 0.2922 0.017 Uiso 1 1 calc R . . . .
C12 C 0.33785(15) 0.66251(14) 0.48932(14) 0.0137(3) Uani 1 1 d . . . . .
C13 C 0.49467(16) 0.72203(14) 0.44501(14) 0.0141(3) Uani 1 1 d . . . . .
H13 H 0.5526 0.7042 0.3470 0.017 Uiso 1 1 calc R . . . .
C14 C 0.56703(15) 0.80480(13) 0.53786(14) 0.0135(3) Uani 1 1 d . . . . .
C15 C 0.73391(15) 0.86974(14) 0.48591(14) 0.0148(3) Uani 1 1 d . . . . .
H15A H 0.8065 0.8356 0.5565 0.018 Uiso 1 1 calc R . . . .
H15B H 0.7198 0.9806 0.4910 0.018 Uiso 1 1 calc R . . . .
C16 C 0.82066(16) 0.82948(14) 0.32997(15) 0.0151(3) Uani 1 1 d . . . . .
H16A H 0.7532 0.8702 0.2575 0.018 Uiso 1 1 calc R . . . .
H16B H 0.8301 0.7187 0.3217 0.018 Uiso 1 1 calc R . . . .
C17 C 0.99203(16) 0.89077(14) 0.29063(15) 0.0171(3) Uani 1 1 d . . . . .
H17A H 0.9821 1.0020 0.2879 0.021 Uiso 1 1 calc R . . . .
H17B H 1.0561 0.8587 0.3686 0.021 Uiso 1 1 calc R . . . .
C18 C 1.08334(17) 0.83533(16) 0.14049(16) 0.0210(3) Uani 1 1 d . . . . .
H18A H 1.0243 0.8732 0.0621 0.032 Uiso 1 1 calc GR . . . .
H18B H 1.0897 0.7252 0.1416 0.032 Uiso 1 1 calc GR . . . .
H18C H 1.1947 0.8720 0.1212 0.032 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
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.5242(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5226(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5362(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5104(18) . ?
C5 C6 1.3801(18) . ?
C5 C14 1.4248(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.4073(18) . ?
C7 C8 1.4400(17) . ?
C7 C12 1.4266(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.3539(19) . ?
C9 C10 1.4431(18) . ?
C9 C10 1.5028(18) 2_566 ?
C10 C9 1.5029(18) 2_566 ?
C10 C11 1.3544(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.4398(18) . ?
C12 C13 1.4166(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.3799(18) . ?
C14 C15 1.5189(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5201(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5276(17) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5250(18) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 C1 111.85(11) . . ?
C3 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C2 C3 C4 114.32(11) . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C3 112.48(10) . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C6 C5 C4 119.78(12) . . ?
C6 C5 C14 119.12(12) . . ?
C14 C5 C4 121.05(11) . . ?
C5 C6 H6 118.5 . . ?
C5 C6 C7 122.95(12) . . ?
C7 C6 H6 118.5 . . ?
C6 C7 C8 120.86(12) . . ?
C6 C7 C12 118.21(12) . . ?
C12 C7 C8 120.93(12) . . ?
C7 C8 H8 121.7 . . ?
C9 C8 C7 116.54(12) . . ?
C9 C8 H8 121.7 . . ?
C8 C9 C10 147.39(12) . 2_566 ?
C8 C9 C10 122.53(12) . . ?
C10 C9 C10 90.07(11) . 2_566 ?
C9 C10 C9 89.93(11) . 2_566 ?
C11 C10 C9 147.36(13) . 2_566 ?
C11 C10 C9 122.70(12) . . ?
C10 C11 H11 121.7 . . ?
C10 C11 C12 116.53(12) . . ?
C12 C11 H11 121.7 . . ?
C7 C12 C11 120.75(12) . . ?
C13 C12 C7 118.10(12) . . ?
C13 C12 C11 121.15(12) . . ?
C12 C13 H13 118.6 . . ?
C14 C13 C12 122.90(12) . . ?
C14 C13 H13 118.6 . . ?
C5 C14 C15 119.71(11) . . ?
C13 C14 C5 118.69(12) . . ?
C13 C14 C15 121.60(11) . . ?
C14 C15 H15A 108.3 . . ?
C14 C15 H15B 108.3 . . ?
C14 C15 C16 116.08(11) . . ?
H15A C15 H15B 107.4 . . ?
C16 C15 H15A 108.3 . . ?
C16 C15 H15B 108.3 . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
C15 C16 C17 112.60(11) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 C16 111.58(11) . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C1 C2 C3 C4 172.70(11) . . . . ?
C2 C3 C4 C5 -73.99(14) . . . . ?
C3 C4 C5 C6 97.61(14) . . . . ?
C3 C4 C5 C14 -80.10(14) . . . . ?
C4 C5 C6 C7 -176.95(11) . . . . ?
C4 C5 C14 C13 176.33(11) . . . . ?
C4 C5 C14 C15 -4.39(18) . . . . ?
C5 C6 C7 C8 -179.77(11) . . . . ?
C5 C6 C7 C12 0.68(19) . . . . ?
C5 C14 C15 C16 176.84(11) . . . . ?
C6 C5 C14 C13 -1.40(18) . . . . ?
C6 C5 C14 C15 177.88(11) . . . . ?
C6 C7 C8 C9 179.94(11) . . . . ?
C6 C7 C12 C11 178.82(11) . . . . ?
C6 C7 C12 C13 -1.53(18) . . . . ?
C7 C8 C9 C10 1.16(18) . . . . ?
C7 C8 C9 C10 179.73(17) . . . 2_566 ?
C7 C12 C13 C14 0.96(19) . . . . ?
C8 C7 C12 C11 -0.72(18) . . . . ?
C8 C7 C12 C13 178.92(11) . . . . ?
C8 C9 C10 C9 179.23(15) . . . 2_566 ?
C8 C9 C10 C11 -0.5(2) . . . . ?
C9 C10 C11 C12 179.69(17) 2_566 . . . ?
C9 C10 C11 C12 -0.74(19) . . . . ?
C10 C9 C10 C9 0.000(1) 2_566 . . 2_566 ?
C10 C9 C10 C11 -179.77(15) 2_566 . . . ?
C10 C11 C12 C7 1.33(18) . . . . ?
C10 C11 C12 C13 -178.31(11) . . . . ?
C11 C12 C13 C14 -179.39(11) . . . . ?
C12 C7 C8 C9 -0.53(18) . . . . ?
C12 C13 C14 C5 0.51(19) . . . . ?
C12 C13 C14 C15 -178.75(11) . . . . ?
C13 C14 C15 C16 -3.91(18) . . . . ?
C14 C5 C6 C7 0.81(19) . . . . ?
C14 C15 C16 C17 -176.24(10) . . . . ?
C15 C16 C17 C18 174.05(11) . . . . ?

####################################################################### 
# 
# 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_cx0925
_database_code_depnum_ccdc_archive 'CCDC 1539451'
_audit_update_record             
;
2017-03-21 deposited with the CCDC.
2017-06-07 downloaded from the CCDC.
;
_audit_creation_date             2017-02-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H14 Br2 Si'
_chemical_formula_sum            'C13 H14 Br2 Si'
_chemical_formula_weight         358.15
_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'
Si Si 0.0817 0.0704 '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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.1961(4)
_cell_length_b                   7.4763(4)
_cell_length_c                   26.1123(14)
_cell_angle_alpha                90
_cell_angle_beta                 95.1754(14)
_cell_angle_gamma                90
_cell_volume                     1399.12(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.149
_cell_measurement_theta_min      3.134
_shelx_estimated_absorpt_T_max   0.830
_shelx_estimated_absorpt_T_min   0.398
_exptl_absorpt_coefficient_mu    5.852
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0741 before and 0.0426 after correction. The Ratio of minimum to maximum transmission is 0.7723. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.033
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            48708
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.198
_diffrn_reflns_theta_min         1.566
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3649
_reflns_number_total             4154
_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 V8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'Bruker SAINT'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         4154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0193
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0189P)²+0.6515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0416
_refine_ls_wR_factor_ref         0.0431
_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:
 C3(H3), C5(H5), C7(H7), C8(H8), C10(H10)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_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 -0.02905(2) 0.55547(2) 0.63331(2) 0.02281(4) Uani 1 1 d . . . . .
Br2 Br 0.96482(2) 0.72939(2) 0.84428(2) 0.02057(4) Uani 1 1 d . . . . .
Si1 Si 0.33251(5) 0.74015(6) 0.57137(2) 0.01860(8) Uani 1 1 d . . . . .
C1 C 0.20867(18) 0.60496(18) 0.66910(6) 0.0173(3) Uani 1 1 d . . . . .
C2 C 0.35110(18) 0.68535(18) 0.64235(5) 0.0156(3) Uani 1 1 d . . . . .
C3 C 0.51616(18) 0.72111(17) 0.67180(5) 0.0148(2) Uani 1 1 d . . . . .
H3 H 0.6143 0.7770 0.6558 0.018 Uiso 1 1 calc R . . . .
C4 C 0.54602(18) 0.67848(17) 0.72477(5) 0.0145(2) Uani 1 1 d . . . . .
C5 C 0.71768(18) 0.71711(17) 0.75381(6) 0.0160(3) Uani 1 1 d . . . . .
H5 H 0.8167 0.7727 0.7380 0.019 Uiso 1 1 calc R . . . .
C6 C 0.73817(19) 0.67312(18) 0.80476(6) 0.0166(3) Uani 1 1 d . . . . .
C7 C 0.5952(2) 0.58972(18) 0.82961(6) 0.0187(3) Uani 1 1 d . . . . .
H7 H 0.6141 0.5601 0.8651 0.022 Uiso 1 1 calc R . . . .
C8 C 0.4292(2) 0.55198(18) 0.80219(6) 0.0184(3) Uani 1 1 d . . . . .
H8 H 0.3326 0.4958 0.8188 0.022 Uiso 1 1 calc R . . . .
C9 C 0.39956(18) 0.59574(17) 0.74923(5) 0.0156(3) Uani 1 1 d . . . . .
C10 C 0.22844(19) 0.56087(18) 0.71994(6) 0.0180(3) Uani 1 1 d . . . . .
H10 H 0.1281 0.5072 0.7356 0.022 Uiso 1 1 calc R . . . .
C11 C 0.1567(2) 0.9198(3) 0.55626(7) 0.0304(4) Uani 1 1 d . . . . .
H11A H 0.0329 0.8763 0.5631 0.046 Uiso 1 1 calc GR . . . .
H11B H 0.1557 0.9531 0.5199 0.046 Uiso 1 1 calc GR . . . .
H11C H 0.1890 1.0246 0.5778 0.046 Uiso 1 1 calc GR . . . .
C12 C 0.2749(2) 0.5350(3) 0.53239(7) 0.0358(4) Uani 1 1 d . . . . .
H12A H 0.3669 0.4416 0.5421 0.054 Uiso 1 1 calc GR . . . .
H12B H 0.2773 0.5631 0.4958 0.054 Uiso 1 1 calc GR . . . .
H12C H 0.1502 0.4928 0.5388 0.054 Uiso 1 1 calc GR . . . .
C13 C 0.5641(2) 0.8246(2) 0.55490(6) 0.0207(3) Uani 1 1 d . . . . .
H13A H 0.5936 0.9366 0.5734 0.031 Uiso 1 1 calc GR . . . .
H13B H 0.5598 0.8460 0.5178 0.031 Uiso 1 1 calc GR . . . .
H13C H 0.6605 0.7355 0.5649 0.031 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 1.9101(14) . ?
Br2 C6 1.8969(14) . ?
Si1 C2 1.8911(15) . ?
Si1 C11 1.8632(17) . ?
Si1 C12 1.8664(18) . ?
Si1 C13 1.8683(15) . ?
C1 C2 1.4244(19) . ?
C1 C10 1.363(2) . ?
C2 C3 1.3816(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.417(2) . ?
C4 C5 1.4196(19) . ?
C4 C9 1.4224(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.366(2) . ?
C6 C7 1.4105(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.365(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.418(2) . ?
C9 C10 1.414(2) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C11 Si1 C2 110.51(7) . . ?
C11 Si1 C12 111.33(9) . . ?
C11 Si1 C13 108.08(8) . . ?
C12 Si1 C2 110.44(8) . . ?
C12 Si1 C13 108.12(7) . . ?
C13 Si1 C2 108.25(6) . . ?
C2 C1 Br1 119.61(11) . . ?
C10 C1 Br1 116.11(10) . . ?
C10 C1 C2 124.28(13) . . ?
C1 C2 Si1 125.57(11) . . ?
C3 C2 Si1 119.00(10) . . ?
C3 C2 C1 115.42(13) . . ?
C2 C3 H3 118.4 . . ?
C2 C3 C4 123.16(12) . . ?
C4 C3 H3 118.4 . . ?
C3 C4 C5 121.58(12) . . ?
C3 C4 C9 118.88(13) . . ?
C5 C4 C9 119.53(13) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 118.93(12) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 Br2 119.25(10) . . ?
C5 C6 C7 122.39(13) . . ?
C7 C6 Br2 118.35(11) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.33(14) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.77(13) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C4 119.05(13) . . ?
C10 C9 C4 118.80(13) . . ?
C10 C9 C8 122.15(13) . . ?
C1 C10 C9 119.45(13) . . ?
C1 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
Si1 C11 H11A 109.5 . . ?
Si1 C11 H11B 109.5 . . ?
Si1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Si1 C12 H12A 109.5 . . ?
Si1 C12 H12B 109.5 . . ?
Si1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si1 C13 H13A 109.5 . . ?
Si1 C13 H13B 109.5 . . ?
Si1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_olex2_date_sample_data_collection 2017-02-07
_olex2_date_sample_submission    2017-02-07
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx0925
_olex2_submission_special_instructions 'No special instructions were received'
