# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_160625
_database_code_depnum_ccdc_archive 'CCDC 1852628'
_audit_update_record             
;
2018-06-30 deposited with the CCDC.
2018-08-01 downloaded from the CCDC.
;

_audit_creation_date             2016-06-25T17:10:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
(1R,3aS,9aS)-1-Azido-2-((tert-butyldimethylsilyl)oxy)-1,3a,4,9a-tetrahydro-5H-cyclopenta[e]pyrrolo[1,2-a]pyrazin-5-one
_chemical_formula_moiety         'C16 H23 Br1 N2 O2 Si1'
_chemical_formula_sum            'C32 H46 Br2 N4 O4 Si2'
_chemical_formula_weight         766.73
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'X,Y,Z '
'-X, 1/2+Y, -Z '
_cell_length_a                   7.0818(2)
_cell_length_b                   34.0727(11)
_cell_length_c                   8.0223(15)
_cell_angle_alpha                90
_cell_angle_beta                 105.239(2)
_cell_angle_gamma                90
_cell_volume                     1867.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    7629
_cell_measurement_theta_min      5.195
_cell_measurement_theta_max      68.14
_cell_measurement_wavelength     1.54178

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.679
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      163(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'curved image-plate'
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       fs_process
_diffrn_orient_matrix_ub_11      -0.067198
_diffrn_orient_matrix_ub_12      0.023114
_diffrn_orient_matrix_ub_13      0.035639
_diffrn_orient_matrix_ub_21      -0.059019
_diffrn_orient_matrix_ub_22      0.006676
_diffrn_orient_matrix_ub_23      -0.124176
_diffrn_orient_matrix_ub_31      -0.115847
_diffrn_orient_matrix_ub_32      -0.016809
_diffrn_orient_matrix_ub_33      -0.00031
_diffrn_measurement_device       'quarter Χ-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-Axis Rapid'
_diffrn_measurement_method       'phi or omega oscillation scans'
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_number            18514
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.192
_diffrn_reflns_theta_max         68.202
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_ful 0.98
_diffrn_reflns_point_group_measured_fraction_max 0.975
_reflns_number_total             6688
_reflns_number_gt                3190
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        
'CrystalClear (Rigaku/MSC Inc., 2006), SORTAV (Blessing, 1995)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1376P)²+5.0614P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6688
_refine_ls_number_parameters     397
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1839
_refine_ls_R_factor_gt           0.0987
_refine_ls_wR_factor_ref         0.3234
_refine_ls_wR_factor_gt          0.2276
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1033 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.046(17)
_refine_diff_density_max         1.008
_refine_diff_density_min         -1.24
_refine_diff_density_rms         0.141

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.170(3) 0.5715(7) 0.886(3) 0.060(6) Uani 1 d . .
H1 H 0.0531 0.5865 0.853 0.072 Uiso 1 calc . .
C2 C 0.180(3) 0.5306(7) 0.893(3) 0.059(6) Uani 1 d . .
H2 H 0.0748 0.5125 0.8647 0.071 Uiso 1 calc . .
C3 C 0.383(3) 0.5222(8) 0.950(3) 0.067(6) Uani 1 d . .
H3 H 0.4409 0.4969 0.97 0.081 Uiso 1 calc . .
C4 C 0.477(3) 0.5564(7) 0.972(3) 0.056(5) Uani 1 d . .
C5 C 0.691(3) 0.5633(7) 1.052(3) 0.058(6) Uani 1 d . .
C6 C 0.626(3) 0.6353(5) 0.996(3) 0.048(5) Uani 1 d . .
H6 H 0.6659 0.6564 1.0847 0.058 Uiso 1 calc . .
C7 C 0.402(3) 0.6283(6) 0.970(3) 0.054(5) Uani 1 d . .
H7 H 0.3596 0.6374 1.073 0.065 Uiso 1 calc . .
C8 C 0.311(3) 0.6534(6) 0.813(3) 0.060(5) Uani 1 d . .
H8 H 0.1749 0.6581 0.7712 0.072 Uiso 1 calc . .
C9 C 0.451(3) 0.6687(6) 0.737(3) 0.052(5) Uani 1 d . .
C10 C 0.652(3) 0.6519(6) 0.825(3) 0.054(5) Uani 1 d . .
H10 H 0.692 0.6312 0.7527 0.065 Uiso 1 calc . .
C11 C 0.212(4) 0.7545(7) 0.679(3) 0.072(7) Uani 1 d . .
H11A H 0.3343 0.7682 0.7329 0.108 Uiso 1 calc . .
H11B H 0.1711 0.7389 0.766 0.108 Uiso 1 calc . .
H11C H 0.1099 0.7738 0.6287 0.108 Uiso 1 calc . .
C12 C 0.024(3) 0.6963(8) 0.405(3) 0.069(6) Uani 1 d . .
H12A H 0.0468 0.6792 0.3144 0.103 Uiso 1 calc . .
H12B H -0.079 0.7153 0.3543 0.103 Uiso 1 calc . .
H12C H -0.0177 0.6804 0.4912 0.103 Uiso 1 calc . .
C13 C 0.361(4) 0.7485(7) 0.354(3) 0.069(7) Uani 1 d . .
C14 C 0.553(4) 0.7693(8) 0.445(4) 0.076(7) Uani 1 d . .
H14A H 0.5289 0.7878 0.53 0.114 Uiso 1 calc . .
H14B H 0.603 0.7835 0.3589 0.114 Uiso 1 calc . .
H14C H 0.6496 0.7497 0.5026 0.114 Uiso 1 calc . .
C15 C 0.213(4) 0.7804(8) 0.254(4) 0.085(8) Uani 1 d . .
H15A H 0.0899 0.7678 0.1943 0.128 Uiso 1 calc . .
H15B H 0.2695 0.7937 0.17 0.128 Uiso 1 calc . .
H15C H 0.189 0.7997 0.3369 0.128 Uiso 1 calc . .
C16 C 0.401(5) 0.7194(7) 0.221(3) 0.080(8) Uani 1 d . .
H16A H 0.2793 0.7062 0.1614 0.12 Uiso 1 calc . .
H16B H 0.497 0.6998 0.2804 0.12 Uiso 1 calc . .
H16C H 0.4534 0.7336 0.1366 0.12 Uiso 1 calc . .
C17 C 0.765(3) 0.5566(7) 0.545(3) 0.060(6) Uani 1 d . .
H17 H 0.862 0.5383 0.6002 0.073 Uiso 1 calc . .
C18 C 0.793(3) 0.5952(6) 0.501(2) 0.049(5) Uani 1 d . .
H18 H 0.9164 0.6078 0.5209 0.059 Uiso 1 calc . .
C19 C 0.609(3) 0.6131(7) 0.422(3) 0.062(6) Uani 1 d . .
H19 H 0.5873 0.6394 0.382 0.074 Uiso 1 calc . .
C20 C 0.472(3) 0.5851(7) 0.417(3) 0.059(6) Uani 1 d . .
C21 C 0.259(3) 0.5841(7) 0.334(3) 0.056(5) Uani 1 d . .
C22 C 0.241(3) 0.5177(6) 0.463(3) 0.058(5) Uani 1 d . .
H22 H 0.2011 0.5207 0.5725 0.07 Uiso 1 calc . .
C23 C 0.470(3) 0.5125(6) 0.499(3) 0.052(5) Uani 1 d . .
H23 H 0.5233 0.501 0.6162 0.062 Uiso 1 calc . .
C24 C 0.493(4) 0.4840(7) 0.368(3) 0.070(6) Uani 1 d . .
H24 H 0.6097 0.4797 0.3336 0.084 Uiso 1 calc . .
C25 C 0.320(3) 0.4647(6) 0.304(3) 0.055(5) Uani 1 d . .
C26 C 0.157(3) 0.4787(6) 0.367(3) 0.064(6) Uani 1 d . .
H26 H 0.0404 0.4843 0.268 0.077 Uiso 1 calc . .
C27 C 0.565(4) 0.3806(8) 0.379(5) 0.110(12) Uani 1 d . .
H27A H 0.6604 0.4011 0.4296 0.166 Uiso 1 calc . .
H27B H 0.6347 0.3562 0.3685 0.166 Uiso 1 calc . .
H27C H 0.4775 0.3762 0.4531 0.166 Uiso 1 calc . .
C28 C 0.582(4) 0.4113(9) 0.028(4) 0.095(9) Uani 1 d . .
H28A H 0.5022 0.4195 -0.0854 0.143 Uiso 1 calc . .
H28B H 0.6651 0.3891 0.0148 0.143 Uiso 1 calc . .
H28C H 0.6647 0.4332 0.0835 0.143 Uiso 1 calc . .
C29 C 0.239(4) 0.3592(6) 0.058(3) 0.072(7) Uani 1 d . .
C30 C 0.100(4) 0.3758(8) -0.112(3) 0.090(9) Uani 1 d . .
H30A H 0.0333 0.3992 -0.0844 0.135 Uiso 1 calc . .
H30B H 0.0031 0.3559 -0.1641 0.135 Uiso 1 calc . .
H30C H 0.1769 0.3829 -0.1927 0.135 Uiso 1 calc . .
C31 C 0.342(5) 0.3233(8) 0.013(5) 0.115(12) Uani 1 d . .
H31A H 0.4259 0.331 -0.0614 0.173 Uiso 1 calc . .
H31B H 0.2449 0.3042 -0.0479 0.173 Uiso 1 calc . .
H31C H 0.423 0.3115 0.1193 0.173 Uiso 1 calc . .
C32 C 0.108(5) 0.3480(10) 0.178(4) 0.109(11) Uani 1 d . .
H32A H 0.0403 0.3715 0.203 0.164 Uiso 1 calc . .
H32B H 0.1896 0.3371 0.2861 0.164 Uiso 1 calc . .
H32C H 0.0115 0.3284 0.1205 0.164 Uiso 1 calc . .
N1 N 0.752(2) 0.6019(5) 1.055(2) 0.055(4) Uani 1 d . .
H1A H 0.878 0.6065 1.0967 0.066 Uiso 1 calc . .
N2 N 0.353(2) 0.5864(5) 0.932(2) 0.054(4) Uani 1 d . .
N3 N 0.165(2) 0.5502(6) 0.341(2) 0.058(5) Uani 1 d . .
H3A H 0.0493 0.5471 0.2685 0.07 Uiso 1 calc . .
N4 N 0.563(2) 0.5504(5) 0.490(2) 0.057(4) Uani 1 d . .
O1 O 0.805(2) 0.5362(4) 1.105(2) 0.068(4) Uani 1 d . .
O2 O 0.427(2) 0.6911(5) 0.5990(18) 0.071(4) Uani 1 d . .
O3 O 0.173(2) 0.6124(5) 0.2484(19) 0.065(4) Uani 1 d . .
O4 O 0.283(2) 0.4345(4) 0.183(2) 0.068(4) Uani 1 d . .
Si1 Si 0.2488(10) 0.72230(18) 0.5095(8) 0.0602(15) Uani 1 d . .
Si2 Si 0.4218(11) 0.39636(19) 0.1635(10) 0.0746(19) Uani 1 d . .
Br1 Br 0.8371(4) 0.69610(8) 0.8717(3) 0.0792(9) Uani 1 d . .
Br2 Br 0.0924(4) 0.44197(8) 0.5253(4) 0.0900(10) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N2 1.35(3) . ?
C1 C2 1.40(3) . ?
C1 H1 0.95 . ?
C2 C3 1.42(3) . ?
C2 H2 0.95 . ?
C3 C4 1.33(3) . ?
C3 H3 0.95 . ?
C4 N2 1.33(3) . ?
C4 C5 1.50(3) . ?
C5 O1 1.23(3) . ?
C5 N1 1.38(3) . ?
C6 N1 1.45(2) . ?
C6 C10 1.54(3) . ?
C6 C7 1.56(3) . ?
C6 H6 1 . ?
C7 N2 1.48(3) . ?
C7 C8 1.52(3) . ?
C7 H7 1 . ?
C8 C9 1.39(3) . ?
C8 H8 0.95 . ?
C9 O2 1.32(2) . ?
C9 C10 1.52(3) . ?
C10 Br1 1.97(2) . ?
C10 H10 1 . ?
C11 Si1 1.82(2) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 Si1 1.82(2) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 C14 1.54(3) . ?
C13 C16 1.54(3) . ?
C13 C15 1.57(3) . ?
C13 Si1 1.87(3) . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 N4 1.40(3) . ?
C17 C18 1.39(3) . ?
C17 H17 0.95 . ?
C18 C19 1.43(3) . ?
C18 H18 0.95 . ?
C19 C20 1.36(3) . ?
C19 H19 0.95 . ?
C20 N4 1.40(3) . ?
C20 C21 1.48(3) . ?
C21 O3 1.25(2) . ?
C21 N3 1.34(3) . ?
C22 N3 1.48(2) . ?
C22 C23 1.58(3) . ?
C22 C26 1.57(3) . ?
C22 H22 1 . ?
C23 C24 1.47(3) . ?
C23 N4 1.46(2) . ?
C23 H23 1 . ?
C24 C25 1.36(3) . ?
C24 H24 0.95 . ?
C25 O4 1.39(3) . ?
C25 C26 1.46(3) . ?
C26 Br2 1.93(2) . ?
C26 H26 1 . ?
C27 Si2 1.84(3) . ?
C27 H27A 0.98 . ?
C27 H27B 0.98 . ?
C27 H27C 0.98 . ?
C28 Si2 1.84(3) . ?
C28 H28A 0.98 . ?
C28 H28B 0.98 . ?
C28 H28C 0.98 . ?
C29 C31 1.51(3) . ?
C29 C32 1.55(4) . ?
C29 C30 1.56(3) . ?
C29 Si2 1.85(2) . ?
C30 H30A 0.98 . ?
C30 H30B 0.98 . ?
C30 H30C 0.98 . ?
C31 H31A 0.98 . ?
C31 H31B 0.98 . ?
C31 H31C 0.98 . ?
C32 H32A 0.98 . ?
C32 H32B 0.98 . ?
C32 H32C 0.98 . ?
N1 H1A 0.88 . ?
N3 H3A 0.88 . ?
O2 Si1 1.660(14) . ?
O4 Si2 1.661(15) . ?

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
N2 C1 C2 109.1(19) . . ?
N2 C1 H1 125.4 . . ?
C2 C1 H1 125.4 . . ?
C3 C2 C1 105(2) . . ?
C3 C2 H2 127.7 . . ?
C1 C2 H2 127.7 . . ?
C4 C3 C2 107(2) . . ?
C4 C3 H3 126.4 . . ?
C2 C3 H3 126.4 . . ?
N2 C4 C3 111(2) . . ?
N2 C4 C5 120.9(19) . . ?
C3 C4 C5 127(2) . . ?
O1 C5 N1 123(2) . . ?
O1 C5 C4 122(2) . . ?
N1 C5 C4 116(2) . . ?
N1 C6 C10 112.0(16) . . ?
N1 C6 C7 116.1(16) . . ?
C10 C6 C7 107.0(16) . . ?
N1 C6 H6 107.1 . . ?
C10 C6 H6 107.1 . . ?
C7 C6 H6 107.1 . . ?
N2 C7 C8 110.4(17) . . ?
N2 C7 C6 110.5(16) . . ?
C8 C7 C6 102.5(16) . . ?
N2 C7 H7 111 . . ?
C8 C7 H7 111 . . ?
C6 C7 H7 111 . . ?
C9 C8 C7 112.3(19) . . ?
C9 C8 H8 123.9 . . ?
C7 C8 H8 123.9 . . ?
O2 C9 C8 129.3(19) . . ?
O2 C9 C10 120.3(18) . . ?
C8 C9 C10 110.1(18) . . ?
C9 C10 C6 103.5(17) . . ?
C9 C10 Br1 107.3(13) . . ?
C6 C10 Br1 109.9(13) . . ?
C9 C10 H10 111.9 . . ?
C6 C10 H10 111.9 . . ?
Br1 C10 H10 111.9 . . ?
Si1 C11 H11A 109.5 . . ?
Si1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Si1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Si1 C12 H12A 109.5 . . ?
Si1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C16 109(2) . . ?
C14 C13 C15 108(2) . . ?
C16 C13 C15 108(2) . . ?
C14 C13 Si1 112.3(17) . . ?
C16 C13 Si1 110.1(16) . . ?
C15 C13 Si1 109.1(17) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C17 C18 105.5(19) . . ?
N4 C17 H17 127.2 . . ?
C18 C17 H17 127.2 . . ?
C17 C18 C19 110.1(19) . . ?
C17 C18 H18 125 . . ?
C19 C18 H18 125 . . ?
C20 C19 C18 106(2) . . ?
C20 C19 H19 127 . . ?
C18 C19 H19 127 . . ?
C19 C20 N4 109(2) . . ?
C19 C20 C21 132(2) . . ?
N4 C20 C21 118(2) . . ?
O3 C21 N3 121(2) . . ?
O3 C21 C20 122(2) . . ?
N3 C21 C20 117.3(19) . . ?
N3 C22 C23 112.4(16) . . ?
N3 C22 C26 106.6(17) . . ?
C23 C22 C26 103.5(17) . . ?
N3 C22 H22 111.3 . . ?
C23 C22 H22 111.3 . . ?
C26 C22 H22 111.3 . . ?
C24 C23 N4 114.6(18) . . ?
C24 C23 C22 104.0(19) . . ?
N4 C23 C22 110.3(16) . . ?
C24 C23 H23 109.2 . . ?
N4 C23 H23 109.2 . . ?
C22 C23 H23 109.2 . . ?
C25 C24 C23 109(2) . . ?
C25 C24 H24 125.3 . . ?
C23 C24 H24 125.3 . . ?
C24 C25 O4 127.3(19) . . ?
C24 C25 C26 115(2) . . ?
O4 C25 C26 117.5(19) . . ?
C25 C26 C22 102.3(18) . . ?
C25 C26 Br2 111.4(13) . . ?
C22 C26 Br2 110.5(16) . . ?
C25 C26 H26 110.8 . . ?
C22 C26 H26 110.8 . . ?
Br2 C26 H26 110.8 . . ?
Si2 C27 H27A 109.5 . . ?
Si2 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
Si2 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
Si2 C28 H28A 109.5 . . ?
Si2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
Si2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C31 C29 C32 111(2) . . ?
C31 C29 C30 109(2) . . ?
C32 C29 C30 107(2) . . ?
C31 C29 Si2 110(2) . . ?
C32 C29 Si2 110.1(18) . . ?
C30 C29 Si2 110.8(17) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C5 N1 C6 125.4(19) . . ?
C5 N1 H1A 117.3 . . ?
C6 N1 H1A 117.3 . . ?
C4 N2 C1 107.9(18) . . ?
C4 N2 C7 125.7(17) . . ?
C1 N2 C7 125.1(18) . . ?
C21 N3 C22 125.2(19) . . ?
C21 N3 H3A 117.4 . . ?
C22 N3 H3A 117.4 . . ?
C20 N4 C17 109.0(19) . . ?
C20 N4 C23 127.1(18) . . ?
C17 N4 C23 123.7(18) . . ?
C9 O2 Si1 130.6(14) . . ?
C25 O4 Si2 129.8(14) . . ?
O2 Si1 C12 111.1(10) . . ?
O2 Si1 C11 107.8(10) . . ?
C12 Si1 C11 110.8(12) . . ?
O2 Si1 C13 100.8(9) . . ?
C12 Si1 C13 113.4(11) . . ?
C11 Si1 C13 112.4(11) . . ?
O4 Si2 C27 109.4(13) . . ?
O4 Si2 C29 102.9(10) . . ?
C27 Si2 C29 112.3(12) . . ?
O4 Si2 C28 108.1(12) . . ?
C27 Si2 C28 111.1(14) . . ?
C29 Si2 C28 112.6(14) . . ?

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
N2 C1 C2 C3 1(3) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C2 C3 C4 N2 0(3) . . . . ?
C2 C3 C4 C5 172(2) . . . . ?
N2 C4 C5 O1 173(2) . . . . ?
C3 C4 C5 O1 1(4) . . . . ?
N2 C4 C5 N1 -10(3) . . . . ?
C3 C4 C5 N1 179(2) . . . . ?
N1 C6 C7 N2 -26(2) . . . . ?
C10 C6 C7 N2 99.5(18) . . . . ?
N1 C6 C7 C8 -144.1(18) . . . . ?
C10 C6 C7 C8 -18(2) . . . . ?
N2 C7 C8 C9 -110(2) . . . . ?
C6 C7 C8 C9 8(2) . . . . ?
C7 C8 C9 O2 179(2) . . . . ?
C7 C8 C9 C10 6(3) . . . . ?
O2 C9 C10 C6 168.9(18) . . . . ?
C8 C9 C10 C6 -17(2) . . . . ?
O2 C9 C10 Br1 53(2) . . . . ?
C8 C9 C10 Br1 -133.3(15) . . . . ?
N1 C6 C10 C9 149.9(17) . . . . ?
C7 C6 C10 C9 22(2) . . . . ?
N1 C6 C10 Br1 -95.7(17) . . . . ?
C7 C6 C10 Br1 135.9(14) . . . . ?
N4 C17 C18 C19 1(2) . . . . ?
C17 C18 C19 C20 -1(2) . . . . ?
C18 C19 C20 N4 0(2) . . . . ?
C18 C19 C20 C21 -172(2) . . . . ?
C19 C20 C21 O3 1(4) . . . . ?
N4 C20 C21 O3 -171.3(19) . . . . ?
C19 C20 C21 N3 175(2) . . . . ?
N4 C20 C21 N3 3(3) . . . . ?
N3 C22 C23 C24 -91(2) . . . . ?
C26 C22 C23 C24 23(2) . . . . ?
N3 C22 C23 N4 32(2) . . . . ?
C26 C22 C23 N4 146.6(17) . . . . ?
N4 C23 C24 C25 -138.3(19) . . . . ?
C22 C23 C24 C25 -18(2) . . . . ?
C23 C24 C25 O4 -177.2(19) . . . . ?
C23 C24 C25 C26 5(3) . . . . ?
C24 C25 C26 C22 11(2) . . . . ?
O4 C25 C26 C22 -167.7(16) . . . . ?
C24 C25 C26 Br2 -107.5(19) . . . . ?
O4 C25 C26 Br2 74(2) . . . . ?
N3 C22 C26 C25 98.6(18) . . . . ?
C23 C22 C26 C25 -20(2) . . . . ?
N3 C22 C26 Br2 -142.7(14) . . . . ?
C23 C22 C26 Br2 98.6(16) . . . . ?
O1 C5 N1 C6 -179(2) . . . . ?
C4 C5 N1 C6 3(3) . . . . ?
C10 C6 N1 C5 -107(2) . . . . ?
C7 C6 N1 C5 16(3) . . . . ?
C3 C4 N2 C1 1(3) . . . . ?
C5 C4 N2 C1 -172(2) . . . . ?
C3 C4 N2 C7 169(2) . . . . ?
C5 C4 N2 C7 -4(4) . . . . ?
C2 C1 N2 C4 -1(3) . . . . ?
C2 C1 N2 C7 -169.0(19) . . . . ?
C8 C7 N2 C4 135(2) . . . . ?
C6 C7 N2 C4 22(3) . . . . ?
C8 C7 N2 C1 -60(3) . . . . ?
C6 C7 N2 C1 -172.5(19) . . . . ?
O3 C21 N3 C22 -168.2(19) . . . . ?
C20 C21 N3 C22 17(3) . . . . ?
C23 C22 N3 C21 -36(3) . . . . ?
C26 C22 N3 C21 -149(2) . . . . ?
C19 C20 N4 C17 0(3) . . . . ?
C21 C20 N4 C17 173.9(19) . . . . ?
C19 C20 N4 C23 -175(2) . . . . ?
C21 C20 N4 C23 -2(3) . . . . ?
C18 C17 N4 C20 -1(2) . . . . ?
C18 C17 N4 C23 174.9(18) . . . . ?
C24 C23 N4 C20 100(2) . . . . ?
C22 C23 N4 C20 -16(3) . . . . ?
C24 C23 N4 C17 -74(3) . . . . ?
C22 C23 N4 C17 168.5(19) . . . . ?
C8 C9 O2 Si1 26(3) . . . . ?
C10 C9 O2 Si1 -161.6(15) . . . . ?
C24 C25 O4 Si2 40(3) . . . . ?
C26 C25 O4 Si2 -141.8(17) . . . . ?
C9 O2 Si1 C12 -71(2) . . . . ?
C9 O2 Si1 C11 50(2) . . . . ?
C9 O2 Si1 C13 168(2) . . . . ?
C14 C13 Si1 O2 -59.7(18) . . . . ?
C16 C13 Si1 O2 61.7(19) . . . . ?
C15 C13 Si1 O2 -179.4(18) . . . . ?
C14 C13 Si1 C12 -178.5(17) . . . . ?
C16 C13 Si1 C12 -57(2) . . . . ?
C15 C13 Si1 C12 62(2) . . . . ?
C14 C13 Si1 C11 55(2) . . . . ?
C16 C13 Si1 C11 176.2(18) . . . . ?
C15 C13 Si1 C11 -65(2) . . . . ?
C25 O4 Si2 C27 33(2) . . . . ?
C25 O4 Si2 C29 152.7(18) . . . . ?
C25 O4 Si2 C28 -88(2) . . . . ?
C31 C29 Si2 O4 174(2) . . . . ?
C32 C29 Si2 O4 -63.5(19) . . . . ?
C30 C29 Si2 O4 54(2) . . . . ?
C31 C29 Si2 C27 -68(2) . . . . ?
C32 C29 Si2 C27 54(2) . . . . ?
C30 C29 Si2 C27 172(2) . . . . ?
C31 C29 Si2 C28 58(2) . . . . ?
C32 C29 Si2 C28 -180(2) . . . . ?
C30 C29 Si2 C28 -62(2) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
