# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_stu8512
_database_code_depnum_ccdc_archive 'CCDC 1502462'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 Br2 N4 O Si'
_chemical_formula_iupac          ?
_chemical_formula_weight         505.27

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   7.0548(3)
_cell_length_b                   10.8999(4)
_cell_length_c                   13.8588(5)
_cell_angle_alpha                73.194(2)
_cell_angle_beta                 85.0620(10)
_cell_angle_gamma                86.312(2)
_cell_volume                     1015.52(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9898
_cell_measurement_theta_min      2.8110
_cell_measurement_theta_max      27.5071
_cell_measurement_temperature    80.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.090
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             502

_exptl_absorpt_coefficient_mu    4.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison,
Wisconsin, USA.'
;
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_T_max  0.71

_exptl_special_details           
;
;

_diffrn_ambient_temperature      80.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            18645
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17

_refine_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_number_total             4658
_reflns_number_gt                4072
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0213
_refine_ls_wR_factor_gt          0.0462
_refine_ls_wR_factor_ref         0.0485
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_number_reflns         4658
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0188P)²+0.6099P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.447
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0061 0.0033 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 v.2014.1--1 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL--2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL--2014 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.33303(2) 0.39269(2) 0.09043(2) 0.01352(5) Uani d . . . 1 . .
Br Br2 0.26189(2) 1.08030(2) 0.29644(2) 0.01533(5) Uani d . . . 1 . .
N N1 0.6949(2) 0.47448(13) 0.38245(10) 0.0089(3) Uani d . . . 1 . .
N N2 0.7669(2) 0.39999(14) 0.47068(10) 0.0096(3) Uani d . . . 1 . .
N N3 0.7408(2) 0.58729(14) 0.53136(10) 0.0098(3) Uani d . . . 1 . .
N N4 0.6704(2) 0.65563(13) 0.44127(10) 0.0087(3) Uani d . . . 1 . .
O O1 0.61168(18) 0.67115(12) 0.27764(9) 0.0118(2) Uani d . . . 1 . .
Si Si1 0.93670(7) 0.21476(5) 0.84398(4) 0.01146(10) Uani d . . . 1 . .
C C1 0.6557(2) 0.60632(16) 0.35970(13) 0.0091(3) Uani d . . . 1 . .
C C2 0.7843(2) 0.46357(16) 0.53861(12) 0.0087(3) Uani d . . . 1 . .
C C3 0.8538(2) 0.38799(16) 0.63359(13) 0.0098(3) Uani d . . . 1 . .
C C4 0.9011(2) 0.32228(17) 0.71437(13) 0.0117(3) Uani d . . . 1 . .
C C5 1.0935(3) 0.07438(18) 0.83427(14) 0.0168(4) Uani d . . . 1 . .
H H5A 1.2238 0.102 0.8129 0.025 Uiso calc U . R 1 . .
H H5B 1.047 0.0375 0.7845 0.025 Uiso calc U . R 1 . .
H H5C 1.0924 0.0097 0.9003 0.025 Uiso calc U . R 1 . .
C C6 0.6924(3) 0.1659(2) 0.89776(14) 0.0204(4) Uani d . . . 1 . .
H H6A 0.6381 0.1197 0.8563 0.031 Uiso calc U . R 1 . .
H H6B 0.6118 0.2424 0.8983 0.031 Uiso calc U . R 1 . .
H H6C 0.6989 0.1099 0.967 0.031 Uiso calc U . R 1 . .
C C7 1.0471(3) 0.30613(19) 0.91765(14) 0.0176(4) Uani d . . . 1 . .
H H7A 1.0635 0.2508 0.9863 0.026 Uiso calc U . R 1 . .
H H7B 0.9643 0.3808 0.9207 0.026 Uiso calc U . R 1 . .
H H7C 1.1714 0.3349 0.8847 0.026 Uiso calc U . R 1 . .
C C11 0.6988(2) 0.41490(16) 0.30211(12) 0.0086(3) Uani d . . . 1 . .
C C12 0.5382(2) 0.42842(16) 0.24734(12) 0.0093(3) Uani d . . . 1 . .
H H12 0.4264 0.4739 0.2636 0.011 Uiso calc U . R 1 . .
C C13 0.5466(2) 0.37365(16) 0.16853(13) 0.0104(3) Uani d . . . 1 . .
C C14 0.7074(3) 0.30433(17) 0.14505(13) 0.0124(3) Uani d . . . 1 . .
H H14 0.7096 0.266 0.0915 0.015 Uiso calc U . R 1 . .
C C15 0.8644(3) 0.29221(17) 0.20112(13) 0.0125(3) Uani d . . . 1 . .
H H15 0.9751 0.2453 0.1855 0.015 Uiso calc U . R 1 . .
C C16 0.8627(2) 0.34762(16) 0.28015(13) 0.0104(3) Uani d . . . 1 . .
H H16 0.9712 0.3395 0.3181 0.013 Uiso calc U . R 1 . .
C C21 0.6502(2) 0.79229(16) 0.42420(12) 0.0090(3) Uani d . . . 1 . .
C C22 0.4897(2) 0.85735(17) 0.37928(12) 0.0103(3) Uani d . . . 1 . .
H H22 0.3915 0.8127 0.363 0.012 Uiso calc U . R 1 . .
C C23 0.4782(2) 0.98926(17) 0.35922(12) 0.0102(3) Uani d . . . 1 . .
C C24 0.6177(2) 1.05730(17) 0.38387(13) 0.0119(3) Uani d . . . 1 . .
H H24 0.6059 1.148 0.3697 0.014 Uiso calc U . R 1 . .
C C25 0.7746(2) 0.98916(17) 0.42963(13) 0.0128(3) Uani d . . . 1 . .
H H25 0.871 1.0339 0.4474 0.015 Uiso calc U . R 1 . .
C C26 0.7932(2) 0.85642(17) 0.44997(13) 0.0105(3) Uani d . . . 1 . .
H H26 0.9016 0.8105 0.4809 0.013 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C13 . 1.8959(17) ?
Br2 C23 . 1.8984(17) ?
N1 N2 . 1.3755(19) ?
N1 C1 . 1.394(2) ?
N1 C11 . 1.440(2) ?
N2 C2 . 1.338(2) ?
N3 C2 . 1.340(2) ?
N3 N4 . 1.3717(19) ?
N4 C1 . 1.399(2) ?
N4 C21 . 1.439(2) ?
O1 C1 . 1.207(2) ?
Si1 C5 . 1.8599(19) ?
Si1 C7 . 1.861(2) ?
Si1 C6 . 1.865(2) ?
Si1 C4 . 1.8670(18) ?
C2 C3 . 1.444(2) ?
C3 C4 . 1.203(2) ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
C11 C16 . 1.388(2) ?
C11 C12 . 1.394(2) ?
C12 C13 . 1.384(2) ?
C12 H12 . 0.95 ?
C13 C14 . 1.390(2) ?
C14 C15 . 1.385(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.394(2) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C21 C26 . 1.389(2) ?
C21 C22 . 1.391(2) ?
C22 C23 . 1.382(2) ?
C22 H22 . 0.95 ?
C23 C24 . 1.391(2) ?
C24 C25 . 1.386(2) ?
C24 H24 . 0.95 ?
C25 C26 . 1.391(2) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C1 . . 124.72(14) ?
N2 N1 C11 . . 115.64(13) ?
C1 N1 C11 . . 118.37(13) ?
C2 N2 N1 . . 113.89(14) ?
C2 N3 N4 . . 114.19(14) ?
N3 N4 C1 . . 124.43(14) ?
N3 N4 C21 . . 115.78(13) ?
C1 N4 C21 . . 118.41(13) ?
C5 Si1 C7 . . 110.42(9) ?
C5 Si1 C6 . . 111.63(9) ?
C7 Si1 C6 . . 111.86(9) ?
C5 Si1 C4 . . 109.17(8) ?
C7 Si1 C4 . . 109.03(9) ?
C6 Si1 C4 . . 104.51(8) ?
O1 C1 N1 . . 123.03(15) ?
O1 C1 N4 . . 123.44(15) ?
N1 C1 N4 . . 113.53(14) ?
N2 C2 N3 . . 128.66(15) ?
N2 C2 C3 . . 115.68(15) ?
N3 C2 C3 . . 115.62(15) ?
C4 C3 C2 . . 176.11(19) ?
C3 C4 Si1 . . 171.56(16) ?
Si1 C5 H5A . . 109.5 ?
Si1 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
Si1 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
Si1 C6 H6A . . 109.5 ?
Si1 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
Si1 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
Si1 C7 H7A . . 109.5 ?
Si1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
Si1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C16 C11 C12 . . 121.84(16) ?
C16 C11 N1 . . 119.32(15) ?
C12 C11 N1 . . 118.83(15) ?
C13 C12 C11 . . 117.99(15) ?
C13 C12 H12 . . 121.0 ?
C11 C12 H12 . . 121.0 ?
C12 C13 C14 . . 121.80(16) ?
C12 C13 Br1 . . 119.34(13) ?
C14 C13 Br1 . . 118.86(13) ?
C15 C14 C13 . . 118.81(16) ?
C15 C14 H14 . . 120.6 ?
C13 C14 H14 . . 120.6 ?
C14 C15 C16 . . 121.17(16) ?
C14 C15 H15 . . 119.4 ?
C16 C15 H15 . . 119.4 ?
C11 C16 C15 . . 118.37(16) ?
C11 C16 H16 . . 120.8 ?
C15 C16 H16 . . 120.8 ?
C26 C21 C22 . . 121.67(16) ?
C26 C21 N4 . . 119.49(15) ?
C22 C21 N4 . . 118.81(15) ?
C23 C22 C21 . . 117.67(16) ?
C23 C22 H22 . . 121.2 ?
C21 C22 H22 . . 121.2 ?
C22 C23 C24 . . 122.57(16) ?
C22 C23 Br2 . . 118.41(13) ?
C24 C23 Br2 . . 119.02(13) ?
C25 C24 C23 . . 118.17(16) ?
C25 C24 H24 . . 120.9 ?
C23 C24 H24 . . 120.9 ?
C24 C25 C26 . . 121.14(16) ?
C24 C25 H25 . . 119.4 ?
C26 C25 H25 . . 119.4 ?
C21 C26 C25 . . 118.76(16) ?
C21 C26 H26 . . 120.6 ?
C25 C26 H26 . . 120.6 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 C2 . . . . 4.8(2) ?
C11 N1 N2 C2 . . . . 171.61(14) ?
C2 N3 N4 C1 . . . . -4.3(2) ?
C2 N3 N4 C21 . . . . -170.65(14) ?
N2 N1 C1 O1 . . . . 171.95(16) ?
C11 N1 C1 O1 . . . . 5.4(2) ?
N2 N1 C1 N4 . . . . -8.7(2) ?
C11 N1 C1 N4 . . . . -175.18(14) ?
N3 N4 C1 O1 . . . . -172.21(16) ?
C21 N4 C1 O1 . . . . -6.2(2) ?
N3 N4 C1 N1 . . . . 8.4(2) ?
C21 N4 C1 N1 . . . . 174.41(14) ?
N1 N2 C2 N3 . . . . 0.2(2) ?
N1 N2 C2 C3 . . . . 178.16(14) ?
N4 N3 C2 N2 . . . . -0.4(2) ?
N4 N3 C2 C3 . . . . -178.36(14) ?
N2 N1 C11 C16 . . . . -45.5(2) ?
C1 N1 C11 C16 . . . . 122.21(17) ?
N2 N1 C11 C12 . . . . 135.55(16) ?
C1 N1 C11 C12 . . . . -56.7(2) ?
C16 C11 C12 C13 . . . . -0.7(2) ?
N1 C11 C12 C13 . . . . 178.16(14) ?
C11 C12 C13 C14 . . . . 1.5(3) ?
C11 C12 C13 Br1 . . . . -178.76(12) ?
C12 C13 C14 C15 . . . . -1.3(3) ?
Br1 C13 C14 C15 . . . . 178.99(13) ?
C13 C14 C15 C16 . . . . 0.2(3) ?
C12 C11 C16 C15 . . . . -0.2(3) ?
N1 C11 C16 C15 . . . . -179.11(15) ?
C14 C15 C16 C11 . . . . 0.5(3) ?
N3 N4 C21 C26 . . . . 42.2(2) ?
C1 N4 C21 C26 . . . . -125.03(17) ?
N3 N4 C21 C22 . . . . -139.75(16) ?
C1 N4 C21 C22 . . . . 53.0(2) ?
C26 C21 C22 C23 . . . . 1.1(2) ?
N4 C21 C22 C23 . . . . -176.91(15) ?
C21 C22 C23 C24 . . . . -1.2(3) ?
C21 C22 C23 Br2 . . . . 179.25(12) ?
C22 C23 C24 C25 . . . . 0.5(3) ?
Br2 C23 C24 C25 . . . . -179.98(13) ?
C23 C24 C25 C26 . . . . 0.4(3) ?
C22 C21 C26 C25 . . . . -0.3(3) ?
N4 C21 C26 C25 . . . . 177.71(15) ?
C24 C25 C26 C21 . . . . -0.5(3) ?

####################################################################### 
# 
# 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_stu7865
_database_code_depnum_ccdc_archive 'CCDC 1502459'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 Br2 N4 O Si'
_chemical_formula_weight         505.28

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'
N N 0.0061 0.0033 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.13720(10)
_cell_length_b                   10.9703(3)
_cell_length_c                   13.9865(4)
_cell_angle_alpha                72.9110(10)
_cell_angle_beta                 86.1540(10)
_cell_angle_gamma                86.504(2)
_cell_volume                     1043.42(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2608
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             502
_exptl_absorpt_coefficient_mu    3.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6272
_exptl_absorpt_correction_T_max  0.8905
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9882
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.19
_diffrn_reflns_theta_max         28.49
_reflns_number_total             5111
_reflns_number_gt                4061
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0215P)²+3.4861P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5111
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1217
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.66357(7) 0.89301(5) 0.09448(4) 0.05231(15) Uani 1 1 d . . .
Br2 Br -0.73569(7) 1.57378(5) 0.29842(5) 0.05978(17) Uani 1 1 d . . .
Si1 Si -0.06457(18) 0.71714(13) 0.84532(9) 0.0438(3) Uani 1 1 d . . .
N1 N -0.2965(5) 0.9742(3) 0.3840(2) 0.0331(7) Uani 1 1 d . . .
N2 N -0.2283(5) 0.9005(3) 0.4724(2) 0.0360(7) Uani 1 1 d . . .
N3 N -0.2531(5) 1.0858(3) 0.5313(2) 0.0362(7) Uani 1 1 d . . .
N4 N -0.3202(5) 1.1548(3) 0.4407(2) 0.0340(7) Uani 1 1 d . . .
O1 O -0.3797(4) 1.1703(3) 0.2786(2) 0.0432(7) Uani 1 1 d . . .
C1 C -0.3356(6) 1.1055(4) 0.3601(3) 0.0338(8) Uani 1 1 d . . .
C2 C -0.2110(5) 0.9634(4) 0.5396(3) 0.0319(8) Uani 1 1 d . . .
C3 C -0.1466(5) 0.8880(4) 0.6353(3) 0.0340(8) Uani 1 1 d . . .
C4 C -0.1016(6) 0.8221(4) 0.7164(3) 0.0410(9) Uani 1 1 d . . .
C5 C 0.0884(8) 0.5773(5) 0.8372(4) 0.0612(14) Uani 1 1 d . . .
H5A H 0.0397 0.5398 0.7897 0.092 Uiso 1 1 calc R . .
H5B H 0.0907 0.5146 0.9025 0.092 Uiso 1 1 calc R . .
H5C H 0.2149 0.6045 0.8150 0.092 Uiso 1 1 calc R . .
C6 C -0.3037(8) 0.6710(7) 0.8985(4) 0.0687(16) Uani 1 1 d . . .
H6A H -0.3794 0.7468 0.9005 0.103 Uiso 1 1 calc R . .
H6B H -0.2955 0.6136 0.9658 0.103 Uiso 1 1 calc R . .
H6C H -0.3615 0.6284 0.8569 0.103 Uiso 1 1 calc R . .
C7 C 0.0467(8) 0.8085(6) 0.9164(4) 0.0593(13) Uani 1 1 d . . .
H7A H 0.1673 0.8366 0.8839 0.089 Uiso 1 1 calc R . .
H7B H 0.0650 0.7546 0.9841 0.089 Uiso 1 1 calc R . .
H7C H -0.0338 0.8822 0.9185 0.089 Uiso 1 1 calc R . .
C11 C -0.2951(6) 0.9153(4) 0.3044(3) 0.0332(8) Uani 1 1 d . . .
C12 C -0.4551(6) 0.9279(4) 0.2505(3) 0.0366(9) Uani 1 1 d . . .
H12 H -0.5645 0.9715 0.2666 0.044 Uiso 1 1 calc R . .
C13 C -0.4480(6) 0.8743(4) 0.1728(3) 0.0390(9) Uani 1 1 d . . .
C14 C -0.2916(6) 0.8052(5) 0.1506(3) 0.0457(10) Uani 1 1 d . . .
H14 H -0.2909 0.7673 0.0984 0.055 Uiso 1 1 calc R . .
C15 C -0.1361(6) 0.7930(5) 0.2069(4) 0.0459(10) Uani 1 1 d . . .
H15 H -0.0286 0.7463 0.1926 0.055 Uiso 1 1 calc R . .
C16 C -0.1355(6) 0.8485(4) 0.2840(3) 0.0398(9) Uani 1 1 d . . .
H16 H -0.0286 0.8406 0.3215 0.048 Uiso 1 1 calc R . .
C21 C -0.3416(6) 1.2901(4) 0.4233(3) 0.0337(8) Uani 1 1 d . . .
C22 C -0.5033(6) 1.3535(4) 0.3799(3) 0.0362(9) Uani 1 1 d . . .
H22 H -0.5994 1.3088 0.3642 0.043 Uiso 1 1 calc R . .
C23 C -0.5175(6) 1.4840(4) 0.3607(3) 0.0404(9) Uani 1 1 d . . .
C24 C -0.3802(6) 1.5519(4) 0.3849(3) 0.0417(10) Uani 1 1 d . . .
H24 H -0.3936 1.6410 0.3712 0.050 Uiso 1 1 calc R . .
C25 C -0.2239(6) 1.4859(4) 0.4293(4) 0.0471(11) Uani 1 1 d . . .
H25 H -0.1297 1.5307 0.4466 0.057 Uiso 1 1 calc R . .
C26 C -0.2025(6) 1.3553(4) 0.4489(3) 0.0408(9) Uani 1 1 d . . .
H26 H -0.0948 1.3112 0.4793 0.049 Uiso 1 1 calc R . .


_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 C13 1.914(4) . ?
Br2 C23 1.909(4) . ?
Si1 C7 1.847(5) . ?
Si1 C6 1.854(6) . ?
Si1 C5 1.855(6) . ?
Si1 C4 1.858(4) . ?
N1 N2 1.366(4) . ?
N1 C1 1.395(5) . ?
N1 C11 1.441(5) . ?
N2 C2 1.336(5) . ?
N3 C2 1.331(5) . ?
N3 N4 1.371(4) . ?
N4 C1 1.399(5) . ?
N4 C21 1.432(5) . ?
O1 C1 1.204(5) . ?
C2 C3 1.440(5) . ?
C3 C4 1.205(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C11 C16 1.376(6) . ?
C11 C12 1.387(5) . ?
C12 C13 1.376(6) . ?
C12 H12 0.9400 . ?
C13 C14 1.381(6) . ?
C14 C15 1.380(6) . ?
C14 H14 0.9400 . ?
C15 C16 1.385(6) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C21 C26 1.382(5) . ?
C21 C22 1.390(5) . ?
C22 C23 1.376(6) . ?
C22 H22 0.9400 . ?
C23 C24 1.382(6) . ?
C24 C25 1.373(6) . ?
C24 H24 0.9400 . ?
C25 C26 1.378(6) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?

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
C7 Si1 C6 111.5(3) . . ?
C7 Si1 C5 110.6(3) . . ?
C6 Si1 C5 112.2(3) . . ?
C7 Si1 C4 109.0(2) . . ?
C6 Si1 C4 104.6(2) . . ?
C5 Si1 C4 108.7(2) . . ?
N2 N1 C1 124.8(3) . . ?
N2 N1 C11 116.4(3) . . ?
C1 N1 C11 117.8(3) . . ?
C2 N2 N1 114.2(3) . . ?
C2 N3 N4 114.5(3) . . ?
N3 N4 C1 124.2(3) . . ?
N3 N4 C21 116.2(3) . . ?
C1 N4 C21 118.5(3) . . ?
O1 C1 N1 123.6(4) . . ?
O1 C1 N4 123.0(4) . . ?
N1 C1 N4 113.4(3) . . ?
N3 C2 N2 128.5(3) . . ?
N3 C2 C3 115.6(3) . . ?
N2 C2 C3 115.9(3) . . ?
C4 C3 C2 176.6(4) . . ?
C3 C4 Si1 172.7(4) . . ?
Si1 C5 H5A 109.5 . . ?
Si1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Si1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
Si1 C6 H6A 109.5 . . ?
Si1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
Si1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C16 C11 C12 121.9(4) . . ?
C16 C11 N1 119.2(3) . . ?
C12 C11 N1 118.9(3) . . ?
C13 C12 C11 117.7(4) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C12 C13 C14 122.1(4) . . ?
C12 C13 Br1 119.1(3) . . ?
C14 C13 Br1 118.8(3) . . ?
C15 C14 C13 118.4(4) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C16 121.3(4) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C11 C16 C15 118.5(4) . . ?
C11 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
C26 C21 C22 121.3(4) . . ?
C26 C21 N4 120.0(4) . . ?
C22 C21 N4 118.7(3) . . ?
C23 C22 C21 117.5(4) . . ?
C23 C22 H22 121.2 . . ?
C21 C22 H22 121.2 . . ?
C22 C23 C24 122.5(4) . . ?
C22 C23 Br2 118.4(3) . . ?
C24 C23 Br2 119.1(3) . . ?
C25 C24 C23 118.4(4) . . ?
C25 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
C24 C25 C26 121.2(4) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C25 C26 C21 119.1(4) . . ?
C25 C26 H26 120.5 . . ?
C21 C26 H26 120.5 . . ?

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 N1 N2 C2 3.9(5) . . . . ?
C11 N1 N2 C2 172.3(3) . . . . ?
C2 N3 N4 C1 -3.3(5) . . . . ?
C2 N3 N4 C21 -171.4(3) . . . . ?
N2 N1 C1 O1 173.2(4) . . . . ?
C11 N1 C1 O1 4.9(6) . . . . ?
N2 N1 C1 N4 -7.4(5) . . . . ?
C11 N1 C1 N4 -175.6(3) . . . . ?
N3 N4 C1 O1 -173.5(4) . . . . ?
C21 N4 C1 O1 -5.7(6) . . . . ?
N3 N4 C1 N1 7.0(5) . . . . ?
C21 N4 C1 N1 174.9(3) . . . . ?
N4 N3 C2 N2 -1.0(6) . . . . ?
N4 N3 C2 C3 -177.9(3) . . . . ?
N1 N2 C2 N3 0.8(6) . . . . ?
N1 N2 C2 C3 177.6(3) . . . . ?
N3 C2 C3 C4 105(8) . . . . ?
N2 C2 C3 C4 -72(8) . . . . ?
C2 C3 C4 Si1 -15(10) . . . . ?
C7 Si1 C4 C3 -119(3) . . . . ?
C6 Si1 C4 C3 0(3) . . . . ?
C5 Si1 C4 C3 120(3) . . . . ?
N2 N1 C11 C16 -46.6(5) . . . . ?
C1 N1 C11 C16 122.6(4) . . . . ?
N2 N1 C11 C12 133.4(4) . . . . ?
C1 N1 C11 C12 -57.3(5) . . . . ?
C16 C11 C12 C13 -2.0(6) . . . . ?
N1 C11 C12 C13 177.9(4) . . . . ?
C11 C12 C13 C14 2.8(7) . . . . ?
C11 C12 C13 Br1 -178.5(3) . . . . ?
C12 C13 C14 C15 -1.8(7) . . . . ?
Br1 C13 C14 C15 179.5(4) . . . . ?
C13 C14 C15 C16 0.0(7) . . . . ?
C12 C11 C16 C15 0.3(7) . . . . ?
N1 C11 C16 C15 -179.6(4) . . . . ?
C14 C15 C16 C11 0.7(7) . . . . ?
N3 N4 C21 C26 43.7(5) . . . . ?
C1 N4 C21 C26 -125.1(4) . . . . ?
N3 N4 C21 C22 -136.8(4) . . . . ?
C1 N4 C21 C22 54.4(5) . . . . ?
C26 C21 C22 C23 1.7(6) . . . . ?
N4 C21 C22 C23 -177.8(4) . . . . ?
C21 C22 C23 C24 -1.3(7) . . . . ?
C21 C22 C23 Br2 178.7(3) . . . . ?
C22 C23 C24 C25 0.3(7) . . . . ?
Br2 C23 C24 C25 -179.8(4) . . . . ?
C23 C24 C25 C26 0.5(7) . . . . ?
C24 C25 C26 C21 0.0(7) . . . . ?
C22 C21 C26 C25 -1.1(7) . . . . ?
N4 C21 C26 C25 178.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        28.49
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.093
####################################################################### 
# 
# 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_stu8498-100
_database_code_depnum_ccdc_archive 'CCDC 1502460'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 Br2 N4 O Si'
_chemical_formula_weight         505.28

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'
N N 0.0061 0.0033 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1059(5)
_cell_length_b                   10.9332(8)
_cell_length_c                   13.9604(11)
_cell_angle_alpha                72.976(3)
_cell_angle_beta                 85.718(3)
_cell_angle_gamma                86.366(4)
_cell_volume                     1033.19(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2157
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             502
_exptl_absorpt_coefficient_mu    3.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3521
_exptl_absorpt_correction_T_max  0.9243
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7790
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_av_sigmaI/netI    0.0687
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.07
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3434
_reflns_number_gt                2929
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0771P)²+3.4127P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3434
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1699
_refine_ls_wR_factor_gt          0.1571
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.73668(9) -0.57686(6) 0.70223(6) 0.0507(3) Uani 1 1 d . . .
Br2 Br 0.66461(8) 0.10654(7) 0.90675(5) 0.0457(2) Uani 1 1 d . . .
Si1 Si 0.0640(2) 0.28393(18) 0.15496(13) 0.0397(4) Uani 1 1 d . . .
O1 O 0.3830(6) -0.1712(4) 0.7218(3) 0.0383(9) Uani 1 1 d . . .
N1 N 0.3238(6) -0.1553(5) 0.5594(4) 0.0330(10) Uani 1 1 d . . .
N2 N 0.2546(6) -0.0864(5) 0.4688(4) 0.0343(11) Uani 1 1 d . . .
N3 N 0.2295(6) 0.0995(4) 0.5282(4) 0.0323(10) Uani 1 1 d . . .
N4 N 0.2993(6) 0.0242(5) 0.6172(4) 0.0324(10) Uani 1 1 d . . .
C1 C 0.3382(7) -0.1061(6) 0.6403(5) 0.0337(12) Uani 1 1 d . . .
C2 C 0.2125(7) 0.0362(5) 0.4610(4) 0.0306(12) Uani 1 1 d . . .
C3 C 0.1454(8) 0.1126(6) 0.3655(4) 0.0332(12) Uani 1 1 d . . .
C4 C 0.1007(8) 0.1765(6) 0.2849(5) 0.0387(13) Uani 1 1 d . . .
C5 C -0.0478(11) 0.1926(8) 0.0832(5) 0.0526(17) Uani 1 1 d . . .
H5A H -0.1687 0.1619 0.1174 0.079 Uiso 1 1 calc R . .
H5B H 0.0356 0.1193 0.0787 0.079 Uiso 1 1 calc R . .
H5C H -0.0695 0.2482 0.0155 0.079 Uiso 1 1 calc R . .
C6 C 0.3055(10) 0.3321(9) 0.1012(6) 0.061(2) Uani 1 1 d . . .
H6A H 0.2971 0.3909 0.0334 0.092 Uiso 1 1 calc R . .
H6B H 0.3833 0.2558 0.0982 0.092 Uiso 1 1 calc R . .
H6C H 0.3632 0.3748 0.1437 0.092 Uiso 1 1 calc R . .
C7 C -0.0905(10) 0.4244(7) 0.1630(6) 0.0524(17) Uani 1 1 d . . .
H7A H -0.0295 0.4722 0.2006 0.079 Uiso 1 1 calc R . .
H7B H -0.2119 0.3950 0.1975 0.079 Uiso 1 1 calc R . .
H7C H -0.1117 0.4800 0.0952 0.079 Uiso 1 1 calc R . .
C11 C 0.3460(8) -0.2914(6) 0.5763(5) 0.0343(12) Uani 1 1 d . . .
C12 C 0.5061(8) -0.3560(6) 0.6199(5) 0.0360(13) Uani 1 1 d . . .
H12 H 0.6042 -0.3109 0.6352 0.043 Uiso 1 1 calc R . .
C13 C 0.5200(8) -0.4875(6) 0.6405(5) 0.0342(12) Uani 1 1 d . . .
C14 C 0.3810(8) -0.5553(6) 0.6154(5) 0.0379(13) Uani 1 1 d . . .
H14 H 0.3941 -0.6457 0.6287 0.046 Uiso 1 1 calc R . .
C15 C 0.2248(8) -0.4885(6) 0.5709(5) 0.0407(14) Uani 1 1 d . . .
H15 H 0.1291 -0.5337 0.5535 0.049 Uiso 1 1 calc R . .
C16 C 0.2035(8) -0.3570(6) 0.5510(5) 0.0375(13) Uani 1 1 d . . .
H16 H 0.0943 -0.3120 0.5206 0.045 Uiso 1 1 calc R . .
C21 C 0.2974(7) 0.0848(5) 0.6966(4) 0.0299(12) Uani 1 1 d . . .
C22 C 0.4567(8) 0.0717(6) 0.7512(5) 0.0342(12) Uani 1 1 d . . .
H22 H 0.5672 0.0261 0.7354 0.041 Uiso 1 1 calc R . .
C23 C 0.4510(8) 0.1266(6) 0.8295(4) 0.0358(13) Uani 1 1 d . . .
C24 C 0.2925(9) 0.1950(7) 0.8505(5) 0.0422(14) Uani 1 1 d . . .
H24 H 0.2912 0.2342 0.9030 0.051 Uiso 1 1 calc R . .
C25 C 0.1358(8) 0.2069(6) 0.7959(5) 0.0380(13) Uani 1 1 d . . .
H25 H 0.0261 0.2533 0.8117 0.046 Uiso 1 1 calc R . .
C26 C 0.1359(8) 0.1520(6) 0.7179(4) 0.0349(13) Uani 1 1 d . . .
H26 H 0.0276 0.1603 0.6801 0.042 Uiso 1 1 calc R . .


_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 C13 1.893(6) . ?
Br2 C23 1.892(6) . ?
Si1 C5 1.854(7) . ?
Si1 C7 1.856(8) . ?
Si1 C6 1.865(7) . ?
Si1 C4 1.877(7) . ?
O1 C1 1.205(7) . ?
N1 N2 1.377(7) . ?
N1 C1 1.398(8) . ?
N1 C11 1.437(7) . ?
N2 C2 1.328(8) . ?
N3 C2 1.336(7) . ?
N3 N4 1.382(7) . ?
N4 C1 1.380(8) . ?
N4 C21 1.446(7) . ?
C2 C3 1.447(8) . ?
C3 C4 1.191(9) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C11 C12 1.383(8) . ?
C11 C16 1.399(8) . ?
C12 C13 1.380(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(8) . ?
C14 C15 1.373(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(9) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.384(8) . ?
C21 C22 1.388(8) . ?
C22 C23 1.391(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.373(9) . ?
C24 C25 1.374(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(9) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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
C5 Si1 C7 110.2(3) . . ?
C5 Si1 C6 111.9(4) . . ?
C7 Si1 C6 111.6(4) . . ?
C5 Si1 C4 108.8(3) . . ?
C7 Si1 C4 109.2(3) . . ?
C6 Si1 C4 104.8(3) . . ?
N2 N1 C1 124.3(5) . . ?
N2 N1 C11 115.9(4) . . ?
C1 N1 C11 118.6(5) . . ?
C2 N2 N1 114.3(5) . . ?
C2 N3 N4 113.7(5) . . ?
C1 N4 N3 125.0(5) . . ?
C1 N4 C21 118.6(5) . . ?
N3 N4 C21 115.5(4) . . ?
O1 C1 N4 123.5(5) . . ?
O1 C1 N1 123.1(5) . . ?
N4 C1 N1 113.5(5) . . ?
N2 C2 N3 128.8(5) . . ?
N2 C2 C3 115.8(5) . . ?
N3 C2 C3 115.4(5) . . ?
C4 C3 C2 176.2(6) . . ?
C3 C4 Si1 172.3(5) . . ?
Si1 C5 H5A 109.5 . . ?
Si1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Si1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
Si1 C6 H6A 109.5 . . ?
Si1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
Si1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C11 C16 121.0(5) . . ?
C12 C11 N1 119.3(5) . . ?
C16 C11 N1 119.6(5) . . ?
C13 C12 C11 118.4(5) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C12 C13 C14 121.8(5) . . ?
C12 C13 Br1 118.7(4) . . ?
C14 C13 Br1 119.5(5) . . ?
C15 C14 C13 118.5(6) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 121.5(5) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C11 118.7(6) . . ?
C15 C16 H16 120.6 . . ?
C11 C16 H16 120.6 . . ?
C26 C21 C22 121.5(5) . . ?
C26 C21 N4 119.4(5) . . ?
C22 C21 N4 119.1(5) . . ?
C21 C22 C23 118.6(5) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
C24 C23 C22 120.5(5) . . ?
C24 C23 Br2 120.3(5) . . ?
C22 C23 Br2 119.2(5) . . ?
C23 C24 C25 120.2(6) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C26 120.7(6) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C21 C26 C25 118.5(5) . . ?
C21 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?

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 N1 N2 C2 4.3(7) . . . . ?
C11 N1 N2 C2 171.6(5) . . . . ?
C2 N3 N4 C1 -4.1(7) . . . . ?
C2 N3 N4 C21 -172.5(4) . . . . ?
N3 N4 C1 O1 -173.1(5) . . . . ?
C21 N4 C1 O1 -5.1(8) . . . . ?
N3 N4 C1 N1 7.9(8) . . . . ?
C21 N4 C1 N1 176.0(4) . . . . ?
N2 N1 C1 O1 173.0(5) . . . . ?
C11 N1 C1 O1 6.0(8) . . . . ?
N2 N1 C1 N4 -8.0(7) . . . . ?
C11 N1 C1 N4 -175.0(5) . . . . ?
N1 N2 C2 N3 0.4(8) . . . . ?
N1 N2 C2 C3 178.0(4) . . . . ?
N4 N3 C2 N2 -0.5(8) . . . . ?
N4 N3 C2 C3 -178.1(4) . . . . ?
N2 C2 C3 C4 -85(10) . . . . ?
N3 C2 C3 C4 93(10) . . . . ?
C2 C3 C4 Si1 -14(13) . . . . ?
C5 Si1 C4 C3 129(4) . . . . ?
C7 Si1 C4 C3 -111(4) . . . . ?
C6 Si1 C4 C3 9(4) . . . . ?
N2 N1 C11 C12 138.0(6) . . . . ?
C1 N1 C11 C12 -53.8(8) . . . . ?
N2 N1 C11 C16 -43.6(7) . . . . ?
C1 N1 C11 C16 124.5(6) . . . . ?
C16 C11 C12 C13 -1.8(9) . . . . ?
N1 C11 C12 C13 176.5(5) . . . . ?
C11 C12 C13 C14 2.4(9) . . . . ?
C11 C12 C13 Br1 -178.9(5) . . . . ?
C12 C13 C14 C15 -1.5(9) . . . . ?
Br1 C13 C14 C15 179.8(5) . . . . ?
C13 C14 C15 C16 0.0(10) . . . . ?
C14 C15 C16 C11 0.5(10) . . . . ?
C12 C11 C16 C15 0.5(9) . . . . ?
N1 C11 C16 C15 -177.9(6) . . . . ?
C1 N4 C21 C26 -122.2(6) . . . . ?
N3 N4 C21 C26 47.0(7) . . . . ?
C1 N4 C21 C22 56.4(7) . . . . ?
N3 N4 C21 C22 -134.5(5) . . . . ?
C26 C21 C22 C23 0.7(8) . . . . ?
N4 C21 C22 C23 -177.8(5) . . . . ?
C21 C22 C23 C24 -1.6(9) . . . . ?
C21 C22 C23 Br2 178.6(4) . . . . ?
C22 C23 C24 C25 1.7(10) . . . . ?
Br2 C23 C24 C25 -178.4(5) . . . . ?
C23 C24 C25 C26 -1.0(10) . . . . ?
C22 C21 C26 C25 0.1(9) . . . . ?
N4 C21 C26 C25 178.6(5) . . . . ?
C24 C25 C26 C21 0.1(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.945
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.945
_refine_diff_density_max         0.836
_refine_diff_density_min         -0.962
_refine_diff_density_rms         0.121
####################################################################### 
# 
# 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_stu8498
_database_code_depnum_ccdc_archive 'CCDC 1502461'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 Br2 N4 O Si'
_chemical_formula_iupac          ?
_chemical_formula_weight         505.27

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   7.0581(2)
_cell_length_b                   10.8956(3)
_cell_length_c                   13.8636(4)
_cell_angle_alpha                73.1680(10)
_cell_angle_beta                 85.1820(10)
_cell_angle_gamma                86.3520(10)
_cell_volume                     1016.00(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      3.3384
_cell_measurement_theta_max      66.5654
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             502

_exptl_absorpt_coefficient_mu    5.765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison,
Wisconsin, USA.'
;
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_T_max  0.89

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine--focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'CuK\a '
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'KappaCCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            17434
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         66.70
_diffrn_reflns_theta_full        66.70
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_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_number_total             3572
_reflns_number_gt                3436
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0869
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_number_reflns         3572
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0373P)²+1.7548P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.919
_refine_diff_density_min         -0.443
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0311 0.0180 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 v.2014.1-----1 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX2 v.2014.1-----1 (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 v.2014.1-----1 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.73783(5) -0.07980(3) 0.70336(2) 0.02372(12) Uani d . . . 1 . .
Br Br2 0.66659(4) 0.60702(3) 0.90903(2) 0.02122(11) Uani d . . . 1 . .
N N1 0.3283(4) 0.3444(2) 0.55905(17) 0.0158(5) Uani d . . . 1 . .
N N2 0.2586(3) 0.4130(2) 0.46880(17) 0.0158(5) Uani d . . . 1 . .
N N3 0.2328(3) 0.5995(2) 0.52945(17) 0.0160(5) Uani d . . . 1 . .
N N4 0.3040(3) 0.5256(2) 0.61740(17) 0.0150(5) Uani d . . . 1 . .
O O1 0.3875(3) 0.32853(19) 0.72228(15) 0.0187(4) Uani d . . . 1 . .
Si Si1 0.06342(12) 0.78505(8) 0.15584(6) 0.01850(18) Uani d . . . 1 . .
C C1 0.3435(4) 0.3935(3) 0.6404(2) 0.0150(6) Uani d . . . 1 . .
C C2 0.2152(4) 0.5363(3) 0.4613(2) 0.0148(6) Uani d . . . 1 . .
C C3 0.1457(4) 0.6118(3) 0.3664(2) 0.0162(6) Uani d . . . 1 . .
C C4 0.0987(4) 0.6775(3) 0.2856(2) 0.0182(6) Uani d . . . 1 . .
C C5 -0.0472(5) 0.6938(3) 0.0823(2) 0.0259(7) Uani d . . . 1 . .
H H5A -0.0629 0.749 0.0135 0.039 Uiso calc U . R 1 . .
H H5B -0.1719 0.6657 0.115 0.039 Uiso calc U . R 1 . .
H H5C 0.0348 0.6187 0.0797 0.039 Uiso calc U . R 1 . .
C C6 0.3075(5) 0.8339(4) 0.1018(2) 0.0311(8) Uani d . . . 1 . .
H H6A 0.3878 0.7573 0.1012 0.047 Uiso calc U . R 1 . .
H H6B 0.3622 0.88 0.1432 0.047 Uiso calc U . R 1 . .
H H6C 0.3006 0.89 0.0326 0.047 Uiso calc U . R 1 . .
C C7 -0.0936(5) 0.9255(3) 0.1653(2) 0.0244(7) Uani d . . . 1 . .
H H7A -0.0452 0.964 0.2136 0.037 Uiso calc U . R 1 . .
H H7B -0.223 0.8974 0.1884 0.037 Uiso calc U . R 1 . .
H H7C -0.0953 0.9892 0.0989 0.037 Uiso calc U . R 1 . .
C C11 0.3487(4) 0.2080(3) 0.5757(2) 0.0156(6) Uani d . . . 1 . .
C C12 0.5092(4) 0.1428(3) 0.6206(2) 0.0158(6) Uani d . . . 1 . .
H H12 0.6074 0.1876 0.6369 0.019 Uiso calc U . R 1 . .
C C13 0.5210(4) 0.0109(3) 0.6406(2) 0.0176(6) Uani d . . . 1 . .
C C14 0.3820(4) -0.0571(3) 0.6161(2) 0.0189(6) Uani d . . . 1 . .
H H14 0.3938 -0.1479 0.6303 0.023 Uiso calc U . R 1 . .
C C15 0.2260(4) 0.0108(3) 0.5703(2) 0.0186(6) Uani d . . . 1 . .
H H15 0.1302 -0.0341 0.5521 0.022 Uiso calc U . R 1 . .
C C16 0.2059(4) 0.1436(3) 0.5503(2) 0.0182(6) Uani d . . . 1 . .
H H16 0.0967 0.1892 0.5198 0.022 Uiso calc U . R 1 . .
C C21 0.3009(4) 0.5846(3) 0.6979(2) 0.0151(6) Uani d . . . 1 . .
C C22 0.4619(4) 0.5714(3) 0.7525(2) 0.0159(6) Uani d . . . 1 . .
H H22 0.5738 0.5262 0.7362 0.019 Uiso calc U . R 1 . .
C C23 0.4533(4) 0.6264(3) 0.8309(2) 0.0170(6) Uani d . . . 1 . .
C C24 0.2930(4) 0.6954(3) 0.8543(2) 0.0183(6) Uani d . . . 1 . .
H H24 0.2911 0.7337 0.9078 0.022 Uiso calc U . R 1 . .
C C25 0.1354(4) 0.7075(3) 0.7982(2) 0.0195(6) Uani d . . . 1 . .
H H25 0.0248 0.7543 0.8139 0.023 Uiso calc U . R 1 . .
C C26 0.1366(4) 0.6522(3) 0.7195(2) 0.0163(6) Uani d . . . 1 . .
H H26 0.0282 0.6603 0.6815 0.02 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C13 . 1.899(3) ?
Br2 C23 . 1.894(3) ?
N1 N2 . 1.371(3) ?
N1 C1 . 1.394(4) ?
N1 C11 . 1.436(4) ?
N2 C2 . 1.335(4) ?
N3 C2 . 1.338(4) ?
N3 N4 . 1.368(3) ?
N4 C1 . 1.396(4) ?
N4 C21 . 1.439(4) ?
O1 C1 . 1.205(3) ?
Si1 C5 . 1.859(3) ?
Si1 C7 . 1.861(3) ?
Si1 C6 . 1.865(4) ?
Si1 C4 . 1.868(3) ?
C2 C3 . 1.442(4) ?
C3 C4 . 1.202(4) ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
C11 C16 . 1.388(4) ?
C11 C12 . 1.391(4) ?
C12 C13 . 1.382(4) ?
C12 H12 . 0.95 ?
C13 C14 . 1.386(4) ?
C14 C15 . 1.380(4) ?
C14 H14 . 0.95 ?
C15 C16 . 1.392(4) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C21 C26 . 1.392(4) ?
C21 C22 . 1.395(4) ?
C22 C23 . 1.380(4) ?
C22 H22 . 0.95 ?
C23 C24 . 1.387(4) ?
C24 C25 . 1.388(4) ?
C24 H24 . 0.95 ?
C25 C26 . 1.390(4) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C1 . . 124.5(2) ?
N2 N1 C11 . . 115.7(2) ?
C1 N1 C11 . . 118.6(2) ?
C2 N2 N1 . . 114.3(2) ?
C2 N3 N4 . . 114.2(2) ?
N3 N4 C1 . . 124.7(2) ?
N3 N4 C21 . . 116.1(2) ?
C1 N4 C21 . . 118.0(2) ?
C5 Si1 C7 . . 110.26(15) ?
C5 Si1 C6 . . 111.77(16) ?
C7 Si1 C6 . . 111.73(16) ?
C5 Si1 C4 . . 109.04(14) ?
C7 Si1 C4 . . 109.12(14) ?
C6 Si1 C4 . . 104.72(14) ?
O1 C1 N1 . . 123.4(3) ?
O1 C1 N4 . . 123.2(3) ?
N1 C1 N4 . . 113.4(2) ?
N2 C2 N3 . . 128.4(3) ?
N2 C2 C3 . . 115.7(2) ?
N3 C2 C3 . . 115.9(2) ?
C4 C3 C2 . . 176.0(3) ?
C3 C4 Si1 . . 171.6(3) ?
Si1 C5 H5A . . 109.5 ?
Si1 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
Si1 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
Si1 C6 H6A . . 109.5 ?
Si1 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
Si1 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
Si1 C7 H7A . . 109.5 ?
Si1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
Si1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C16 C11 C12 . . 121.5(3) ?
C16 C11 N1 . . 119.6(3) ?
C12 C11 N1 . . 118.8(3) ?
C13 C12 C11 . . 117.8(3) ?
C13 C12 H12 . . 121.1 ?
C11 C12 H12 . . 121.1 ?
C12 C13 C14 . . 122.6(3) ?
C12 C13 Br1 . . 118.3(2) ?
C14 C13 Br1 . . 119.1(2) ?
C15 C14 C13 . . 118.1(3) ?
C15 C14 H14 . . 121.0 ?
C13 C14 H14 . . 121.0 ?
C14 C15 C16 . . 121.5(3) ?
C14 C15 H15 . . 119.2 ?
C16 C15 H15 . . 119.2 ?
C11 C16 C15 . . 118.5(3) ?
C11 C16 H16 . . 120.7 ?
C15 C16 H16 . . 120.7 ?
C26 C21 C22 . . 122.0(3) ?
C26 C21 N4 . . 118.9(3) ?
C22 C21 N4 . . 119.0(3) ?
C23 C22 C21 . . 117.8(3) ?
C23 C22 H22 . . 121.1 ?
C21 C22 H22 . . 121.1 ?
C22 C23 C24 . . 122.0(3) ?
C22 C23 Br2 . . 119.1(2) ?
C24 C23 Br2 . . 118.9(2) ?
C23 C24 C25 . . 118.8(3) ?
C23 C24 H24 . . 120.6 ?
C25 C24 H24 . . 120.6 ?
C24 C25 C26 . . 121.2(3) ?
C24 C25 H25 . . 119.4 ?
C26 C25 H25 . . 119.4 ?
C25 C26 C21 . . 118.2(3) ?
C25 C26 H26 . . 120.9 ?
C21 C26 H26 . . 120.9 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 C2 . . . . 3.9(4) ?
C11 N1 N2 C2 . . . . 170.8(2) ?
C2 N3 N4 C1 . . . . -4.6(4) ?
C2 N3 N4 C21 . . . . -171.7(2) ?
N2 N1 C1 O1 . . . . 172.5(3) ?
C11 N1 C1 O1 . . . . 5.9(4) ?
N2 N1 C1 N4 . . . . -7.9(4) ?
C11 N1 C1 N4 . . . . -174.5(2) ?
N3 N4 C1 O1 . . . . -172.1(3) ?
C21 N4 C1 O1 . . . . -5.2(4) ?
N3 N4 C1 N1 . . . . 8.3(4) ?
C21 N4 C1 N1 . . . . 175.3(2) ?
N1 N2 C2 N3 . . . . 0.7(4) ?
N1 N2 C2 C3 . . . . 178.6(2) ?
N4 N3 C2 N2 . . . . -0.4(4) ?
N4 N3 C2 C3 . . . . -178.3(2) ?
N2 N1 C11 C16 . . . . -42.9(4) ?
C1 N1 C11 C16 . . . . 124.9(3) ?
N2 N1 C11 C12 . . . . 139.4(3) ?
C1 N1 C11 C12 . . . . -52.8(4) ?
C16 C11 C12 C13 . . . . -0.9(4) ?
N1 C11 C12 C13 . . . . 176.7(2) ?
C11 C12 C13 C14 . . . . 1.2(4) ?
C11 C12 C13 Br1 . . . . -179.2(2) ?
C12 C13 C14 C15 . . . . -0.3(4) ?
Br1 C13 C14 C15 . . . . -179.9(2) ?
C13 C14 C15 C16 . . . . -0.9(4) ?
C12 C11 C16 C15 . . . . -0.2(4) ?
N1 C11 C16 C15 . . . . -177.8(3) ?
C14 C15 C16 C11 . . . . 1.1(4) ?
N3 N4 C21 C26 . . . . 45.5(4) ?
C1 N4 C21 C26 . . . . -122.6(3) ?
N3 N4 C21 C22 . . . . -135.0(3) ?
C1 N4 C21 C22 . . . . 56.9(4) ?
C26 C21 C22 C23 . . . . 1.0(4) ?
N4 C21 C22 C23 . . . . -178.4(2) ?
C21 C22 C23 C24 . . . . -1.5(4) ?
C21 C22 C23 Br2 . . . . 178.4(2) ?
C22 C23 C24 C25 . . . . 1.2(4) ?
Br2 C23 C24 C25 . . . . -178.8(2) ?
C23 C24 C25 C26 . . . . -0.2(4) ?
C24 C25 C26 C21 . . . . -0.3(4) ?
C22 C21 C26 C25 . . . . -0.1(4) ?
N4 C21 C26 C25 . . . . 179.3(3) ?

