# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
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#                                CCDC 
# 
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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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data_cd21468

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H27 Br N2 O2 S'
_chemical_formula_weight         643.57

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3013(15)
_cell_length_b                   13.0206(18)
_cell_length_c                   13.9427(18)
_cell_angle_alpha                117.359(3)
_cell_angle_beta                 105.117(3)
_cell_angle_gamma                95.850(3)
_cell_volume                     1548.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1929
_cell_measurement_theta_min      4.825
_cell_measurement_theta_max      44.671

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             660
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.114
_exptl_absorpt_coefficient_mu    1.431
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6317
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9421
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.754
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6082
_reflns_number_gt                3794
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0819P)²+0.4899P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6082
_refine_ls_number_parameters     447
_refine_ls_number_restraints     85
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1669
_refine_ls_wR_factor_gt          0.1436
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.02279(6) 1.05852(5) 1.19611(5) 0.1070(3) Uani 1 1 d . . . . .
S1 S 0.18494(9) 0.45654(8) 0.44675(7) 0.0453(2) Uani 1 1 d . . . . .
N1 N 0.5365(3) 0.6428(2) 0.8123(2) 0.0457(7) Uani 1 1 d . . . . .
N2 N 0.2044(3) 0.5100(2) 0.5812(2) 0.0418(6) Uani 1 1 d D . . . .
O1 O 0.2863(3) 0.3914(2) 0.4237(2) 0.0645(7) Uani 1 1 d . . . . .
O2 O 0.0397(2) 0.3966(2) 0.3862(2) 0.0531(6) Uani 1 1 d . . . . .
C1 C 0.4322(3) 0.6486(3) 0.7309(3) 0.0428(8) Uani 1 1 d . . . . .
C2 C 0.3325(3) 0.5412(3) 0.6704(3) 0.0404(7) Uani 1 1 d . . . . .
C3 C 0.3742(4) 0.4669(3) 0.7154(3) 0.0435(8) Uani 1 1 d . . . . .
C4 C 0.5005(4) 0.5311(3) 0.8023(3) 0.0468(8) Uani 1 1 d . . . . .
C5 C 0.5863(4) 0.4961(3) 0.8732(3) 0.0535(9) Uani 1 1 d . . . . .
C6 C 0.6506(4) 0.4556(3) 0.9242(3) 0.0614(10) Uani 1 1 d . . . . .
C7 C 0.7162(19) 0.3967(18) 0.985(2) 0.062(2) Uani 0.6 1 d D U P A 1
C8 C 0.8394(11) 0.4504(10) 1.0758(8) 0.072(2) Uani 0.6 1 d D U P A 1
H8 H 0.8853 0.5292 1.1040 0.086 Uiso 0.6 1 calc R U P A 1
C9 C 0.8948(12) 0.3873(9) 1.1247(8) 0.071(2) Uani 0.6 1 d D U P A 1
H9 H 0.9810 0.4225 1.1838 0.086 Uiso 0.6 1 calc R U P A 1
C10 C 0.8282(12) 0.2776(9) 1.0894(9) 0.075(2) Uani 0.6 1 d D U P A 1
H10 H 0.8652 0.2397 1.1286 0.090 Uiso 0.6 1 calc R U P A 1
C11 C 0.7055(10) 0.2167(9) 0.9965(8) 0.0733(19) Uani 0.6 1 d D U P A 1
H11 H 0.6632 0.1377 0.9710 0.088 Uiso 0.6 1 calc R U P A 1
C12 C 0.6461(11) 0.2753(8) 0.9416(7) 0.0667(19) Uani 0.6 1 d D U P A 1
H12 H 0.5636 0.2369 0.8786 0.080 Uiso 0.6 1 calc R U P A 1
C7' C 0.728(3) 0.408(3) 0.984(3) 0.073(4) Uani 0.4 1 d D U P A 2
C8' C 0.8670(18) 0.4690(16) 1.0510(12) 0.079(3) Uani 0.4 1 d D U P A 2
H8' H 0.9087 0.5351 1.0500 0.094 Uiso 0.4 1 calc R U P A 2
C9' C 0.9419(17) 0.4293(14) 1.1188(12) 0.085(3) Uani 0.4 1 d D U P A 2
H9' H 1.0361 0.4651 1.1617 0.102 Uiso 0.4 1 calc R U P A 2
C10' C 0.8732(17) 0.3367(17) 1.1204(14) 0.080(3) Uani 0.4 1 d D U P A 2
H10' H 0.9198 0.3195 1.1759 0.096 Uiso 0.4 1 calc R U P A 2
C11' C 0.7476(17) 0.2684(14) 1.0521(12) 0.077(3) Uani 0.4 1 d D U P A 2
H11' H 0.7148 0.1962 1.0471 0.092 Uiso 0.4 1 calc R U P A 2
C12' C 0.6647(18) 0.3092(16) 0.9864(10) 0.074(3) Uani 0.4 1 d D U P A 2
H12' H 0.5705 0.2714 0.9456 0.089 Uiso 0.4 1 calc R U P A 2
C13 C 0.2999(3) 0.3445(3) 0.6803(3) 0.0451(8) Uani 1 1 d . . . . .
C14 C 0.2915(4) 0.3164(3) 0.7635(3) 0.0583(10) Uani 1 1 d . . . . .
H14 H 0.3291 0.3752 0.8410 0.070 Uiso 1 1 calc R U . . .
C15 C 0.2278(5) 0.2014(4) 0.7319(4) 0.0742(13) Uani 1 1 d . . . . .
H15 H 0.2257 0.1827 0.7884 0.089 Uiso 1 1 calc R U . . .
C16 C 0.1676(5) 0.1146(4) 0.6179(4) 0.0777(14) Uani 1 1 d . . . . .
H16 H 0.1232 0.0377 0.5968 0.093 Uiso 1 1 calc R U . . .
C17 C 0.1735(5) 0.1423(4) 0.5362(4) 0.0776(13) Uani 1 1 d . . . . .
H17 H 0.1323 0.0837 0.4588 0.093 Uiso 1 1 calc R U . . .
C18 C 0.2395(4) 0.2559(3) 0.5656(3) 0.0591(10) Uani 1 1 d . . . . .
H18 H 0.2433 0.2728 0.5083 0.071 Uiso 1 1 calc R U . . .
C19 C 0.4367(4) 0.7544(3) 0.7164(3) 0.0444(8) Uani 1 1 d . . . . .
C20 C 0.3202(4) 0.7974(3) 0.7032(3) 0.0523(9) Uani 1 1 d . . . . .
H20 H 0.2397 0.7606 0.7055 0.063 Uiso 1 1 calc R U . . .
C21 C 0.3212(5) 0.8941(4) 0.6867(4) 0.0639(11) Uani 1 1 d . . . . .
H21 H 0.2415 0.9215 0.6769 0.077 Uiso 1 1 calc R U . . .
C22 C 0.4393(5) 0.9493(4) 0.6849(4) 0.0723(12) Uani 1 1 d . . . . .
H22 H 0.4409 1.0154 0.6751 0.087 Uiso 1 1 calc R U . . .
C23 C 0.5558(5) 0.9077(4) 0.6974(4) 0.0744(12) Uani 1 1 d . . . . .
H23 H 0.6359 0.9452 0.6953 0.089 Uiso 1 1 calc R U . . .
C24 C 0.5553(4) 0.8105(3) 0.7131(3) 0.0564(9) Uani 1 1 d . . . . .
H24 H 0.6348 0.7828 0.7214 0.068 Uiso 1 1 calc R U . . .
C25 C 0.6521(4) 0.7396(3) 0.9022(3) 0.0483(8) Uani 1 1 d . . . . .
C26 C 0.6298(4) 0.8488(3) 0.9701(3) 0.0578(9) Uani 1 1 d . . . . .
H26 H 0.5400 0.8587 0.9580 0.069 Uiso 1 1 calc R U . . .
C27 C 0.7417(5) 0.9431(4) 1.0562(3) 0.0650(11) Uani 1 1 d . . . . .
H27 H 0.7275 1.0173 1.1006 0.078 Uiso 1 1 calc R U . . .
C28 C 0.8719(4) 0.9272(4) 1.0756(3) 0.0634(11) Uani 1 1 d . . . . .
C29 C 0.8957(5) 0.8196(4) 1.0106(4) 0.0739(12) Uani 1 1 d . . . . .
H29 H 0.9855 0.8095 1.0251 0.089 Uiso 1 1 calc R U . . .
C30 C 0.7847(4) 0.7260(4) 0.9230(4) 0.0651(11) Uani 1 1 d . . . . .
H30 H 0.8002 0.6527 0.8775 0.078 Uiso 1 1 calc R U . . .
C31 C 0.2165(4) 0.5746(3) 0.4196(3) 0.0486(8) Uani 1 1 d . . . . .
C32 C 0.1140(4) 0.6326(4) 0.4065(4) 0.0640(11) Uani 1 1 d . . . . .
H32 H 0.0306 0.6122 0.4156 0.077 Uiso 1 1 calc R U . . .
C33 C 0.1362(5) 0.7205(4) 0.3799(4) 0.0759(13) Uani 1 1 d . . . . .
H33 H 0.0668 0.7589 0.3702 0.091 Uiso 1 1 calc R U . . .
C34 C 0.2575(6) 0.7524(4) 0.3674(4) 0.0773(13) Uani 1 1 d . . . . .
C35 C 0.3610(6) 0.6968(4) 0.3837(4) 0.0829(14) Uani 1 1 d . . . . .
H35 H 0.4454 0.7195 0.3771 0.099 Uiso 1 1 calc R U . . .
C36 C 0.3399(4) 0.6069(4) 0.4098(4) 0.0640(11) Uani 1 1 d . . . . .
H36 H 0.4097 0.5691 0.4204 0.077 Uiso 1 1 calc R U . . .
C37 C 0.2836(8) 0.8511(5) 0.3386(6) 0.134(3) Uani 1 1 d . . . . .
H37A H 0.1984 0.8484 0.2876 0.202 Uiso 1 1 calc R U . . .
H37B H 0.3521 0.8392 0.3019 0.202 Uiso 1 1 calc R U . . .
H37C H 0.3167 0.9277 0.4082 0.202 Uiso 1 1 calc R U . . .
H2 H 0.143(3) 0.542(3) 0.597(3) 0.037(9) Uiso 1 1 d D . . . .


_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 C28 1.902(4) . ?
S1 O1 1.421(3) . ?
S1 O2 1.435(2) . ?
S1 N2 1.618(3) . ?
S1 C31 1.763(3) . ?
N1 C1 1.381(4) . ?
N1 C4 1.397(4) . ?
N1 C25 1.429(4) . ?
N2 C2 1.423(4) . ?
N2 H2 0.811(18) . ?
C1 C2 1.376(4) . ?
C1 C19 1.480(4) . ?
C2 C3 1.419(4) . ?
C3 C4 1.373(5) . ?
C3 C13 1.486(5) . ?
C4 C5 1.415(5) . ?
C5 C6 1.181(5) . ?
C6 C7' 1.39(3) . ?
C6 C7 1.474(18) . ?
C7 C8 1.366(13) . ?
C7 C12 1.430(13) . ?
C8 C9 1.369(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.316(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(10) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C7' C8' 1.394(17) . ?
C7' C12' 1.404(18) . ?
C8' C9' 1.381(14) . ?
C8' H8' 0.9300 . ?
C9' C10' 1.347(15) . ?
C9' H9' 0.9300 . ?
C10' C11' 1.311(16) . ?
C10' H10' 0.9300 . ?
C11' C12' 1.408(14) . ?
C11' H11' 0.9300 . ?
C12' H12' 0.9300 . ?
C13 C18 1.384(5) . ?
C13 C14 1.387(5) . ?
C14 C15 1.382(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.357(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.380(5) . ?
C19 C24 1.381(5) . ?
C20 C21 1.380(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.361(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.379(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C30 1.368(5) . ?
C25 C26 1.383(5) . ?
C26 C27 1.382(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.355(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.365(6) . ?
C29 C30 1.380(6) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C36 1.359(5) . ?
C31 C32 1.382(5) . ?
C32 C33 1.371(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.356(7) . ?
C33 H33 0.9300 . ?
C34 C35 1.377(7) . ?
C34 C37 1.532(6) . ?
C35 C36 1.390(6) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.86(17) . . ?
O1 S1 N2 107.74(15) . . ?
O2 S1 N2 104.62(15) . . ?
O1 S1 C31 107.86(17) . . ?
O2 S1 C31 106.61(15) . . ?
N2 S1 C31 109.92(16) . . ?
C1 N1 C4 108.5(3) . . ?
C1 N1 C25 126.1(3) . . ?
C4 N1 C25 124.9(3) . . ?
C2 N2 S1 125.0(2) . . ?
C2 N2 H2 119(2) . . ?
S1 N2 H2 112(2) . . ?
C2 C1 N1 107.4(3) . . ?
C2 C1 C19 129.5(3) . . ?
N1 C1 C19 123.1(3) . . ?
C1 C2 C3 108.9(3) . . ?
C1 C2 N2 126.4(3) . . ?
C3 C2 N2 124.6(3) . . ?
C4 C3 C2 106.5(3) . . ?
C4 C3 C13 124.7(3) . . ?
C2 C3 C13 128.8(3) . . ?
C3 C4 N1 108.6(3) . . ?
C3 C4 C5 128.6(3) . . ?
N1 C4 C5 122.8(3) . . ?
C6 C5 C4 173.4(4) . . ?
C5 C6 C7' 179.3(14) . . ?
C5 C6 C7 173.7(8) . . ?
C8 C7 C12 120.1(13) . . ?
C8 C7 C6 123.6(10) . . ?
C12 C7 C6 116.2(11) . . ?
C7 C8 C9 119.6(11) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 121.0(10) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 122.5(9) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C10 C11 C12 118.8(8) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C11 C12 C7 117.8(11) . . ?
C11 C12 H12 121.1 . . ?
C7 C12 H12 121.1 . . ?
C6 C7' C8' 118.2(17) . . ?
C6 C7' C12' 121.1(18) . . ?
C8' C7' C12' 120(2) . . ?
C9' C8' C7' 118.9(18) . . ?
C9' C8' H8' 120.5 . . ?
C7' C8' H8' 120.5 . . ?
C10' C9' C8' 117.4(16) . . ?
C10' C9' H9' 121.3 . . ?
C8' C9' H9' 121.3 . . ?
C11' C10' C9' 126.8(16) . . ?
C11' C10' H10' 116.6 . . ?
C9' C10' H10' 116.6 . . ?
C10' C11' C12' 116.9(15) . . ?
C10' C11' H11' 121.6 . . ?
C12' C11' H11' 121.6 . . ?
C7' C12' C11' 118.3(18) . . ?
C7' C12' H12' 120.8 . . ?
C11' C12' H12' 120.8 . . ?
C18 C13 C14 118.5(3) . . ?
C18 C13 C3 121.6(3) . . ?
C14 C13 C3 119.9(3) . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.5(4) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 119.2(4) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 121.3(4) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C13 120.0(4) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C20 C19 C24 118.6(3) . . ?
C20 C19 C1 120.2(3) . . ?
C24 C19 C1 121.3(3) . . ?
C21 C20 C19 121.1(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 119.7(4) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.1(4) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C24 120.6(4) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C19 120.0(4) . . ?
C23 C24 H24 120.0 . . ?
C19 C24 H24 120.0 . . ?
C30 C25 C26 119.3(4) . . ?
C30 C25 N1 121.1(3) . . ?
C26 C25 N1 119.6(3) . . ?
C27 C26 C25 119.7(4) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C28 C27 C26 119.9(4) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C27 C28 C29 121.2(4) . . ?
C27 C28 Br1 118.6(3) . . ?
C29 C28 Br1 120.2(3) . . ?
C28 C29 C30 119.1(4) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?
C25 C30 C29 120.8(4) . . ?
C25 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C36 C31 C32 120.3(3) . . ?
C36 C31 S1 120.3(3) . . ?
C32 C31 S1 119.5(3) . . ?
C33 C32 C31 119.4(4) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C34 C33 C32 121.3(5) . . ?
C34 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C33 C34 C35 119.2(4) . . ?
C33 C34 C37 121.6(5) . . ?
C35 C34 C37 119.1(5) . . ?
C34 C35 C36 120.3(4) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C31 C36 C35 119.5(4) . . ?
C31 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 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
O1 S1 N2 C2 29.3(3) . . . . ?
O2 S1 N2 C2 157.9(2) . . . . ?
C31 S1 N2 C2 -88.0(3) . . . . ?
C4 N1 C1 C2 -0.3(4) . . . . ?
C25 N1 C1 C2 -172.2(3) . . . . ?
C4 N1 C1 C19 -179.5(3) . . . . ?
C25 N1 C1 C19 8.6(5) . . . . ?
N1 C1 C2 C3 0.6(4) . . . . ?
C19 C1 C2 C3 179.7(3) . . . . ?
N1 C1 C2 N2 177.5(3) . . . . ?
C19 C1 C2 N2 -3.3(6) . . . . ?
S1 N2 C2 C1 85.4(4) . . . . ?
S1 N2 C2 C3 -98.2(4) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
N2 C2 C3 C4 -177.7(3) . . . . ?
C1 C2 C3 C13 178.5(3) . . . . ?
N2 C2 C3 C13 1.5(6) . . . . ?
C2 C3 C4 N1 0.5(4) . . . . ?
C13 C3 C4 N1 -178.8(3) . . . . ?
C2 C3 C4 C5 -179.2(4) . . . . ?
C13 C3 C4 C5 1.5(6) . . . . ?
C1 N1 C4 C3 -0.1(4) . . . . ?
C25 N1 C4 C3 171.9(3) . . . . ?
C1 N1 C4 C5 179.6(3) . . . . ?
C25 N1 C4 C5 -8.4(5) . . . . ?
C7' C6 C7 C8 31(23) . . . . ?
C7' C6 C7 C12 -147(27) . . . . ?
C12 C7 C8 C9 0(3) . . . . ?
C6 C7 C8 C9 -177.8(17) . . . . ?
C7 C8 C9 C10 -3.2(19) . . . . ?
C8 C9 C10 C11 5.1(16) . . . . ?
C9 C10 C11 C12 -3.4(15) . . . . ?
C10 C11 C12 C7 -0.1(19) . . . . ?
C8 C7 C12 C11 2(3) . . . . ?
C6 C7 C12 C11 179.5(14) . . . . ?
C7 C6 C7' C8' -164(29) . . . . ?
C7 C6 C7' C12' 10(22) . . . . ?
C6 C7' C8' C9' 175(3) . . . . ?
C12' C7' C8' C9' 0(5) . . . . ?
C7' C8' C9' C10' -3(3) . . . . ?
C8' C9' C10' C11' 11(3) . . . . ?
C9' C10' C11' C12' -14(3) . . . . ?
C6 C7' C12' C11' -178(3) . . . . ?
C8' C7' C12' C11' -4(5) . . . . ?
C10' C11' C12' C7' 10(3) . . . . ?
C4 C3 C13 C18 -135.1(4) . . . . ?
C2 C3 C13 C18 45.8(5) . . . . ?
C4 C3 C13 C14 44.0(5) . . . . ?
C2 C3 C13 C14 -135.1(4) . . . . ?
C18 C13 C14 C15 1.9(6) . . . . ?
C3 C13 C14 C15 -177.2(4) . . . . ?
C13 C14 C15 C16 -2.3(7) . . . . ?
C14 C15 C16 C17 1.2(7) . . . . ?
C15 C16 C17 C18 0.3(7) . . . . ?
C16 C17 C18 C13 -0.7(7) . . . . ?
C14 C13 C18 C17 -0.4(6) . . . . ?
C3 C13 C18 C17 178.7(4) . . . . ?
C2 C1 C19 C20 45.8(5) . . . . ?
N1 C1 C19 C20 -135.2(4) . . . . ?
C2 C1 C19 C24 -132.7(4) . . . . ?
N1 C1 C19 C24 46.3(5) . . . . ?
C24 C19 C20 C21 0.2(5) . . . . ?
C1 C19 C20 C21 -178.3(3) . . . . ?
C19 C20 C21 C22 -0.9(6) . . . . ?
C20 C21 C22 C23 1.1(7) . . . . ?
C21 C22 C23 C24 -0.6(7) . . . . ?
C22 C23 C24 C19 -0.1(7) . . . . ?
C20 C19 C24 C23 0.3(6) . . . . ?
C1 C19 C24 C23 178.8(3) . . . . ?
C1 N1 C25 C30 -132.4(4) . . . . ?
C4 N1 C25 C30 56.9(5) . . . . ?
C1 N1 C25 C26 48.1(5) . . . . ?
C4 N1 C25 C26 -122.6(4) . . . . ?
C30 C25 C26 C27 1.4(6) . . . . ?
N1 C25 C26 C27 -179.1(3) . . . . ?
C25 C26 C27 C28 -1.8(6) . . . . ?
C26 C27 C28 C29 0.9(6) . . . . ?
C26 C27 C28 Br1 -179.1(3) . . . . ?
C27 C28 C29 C30 0.5(7) . . . . ?
Br1 C28 C29 C30 -179.4(3) . . . . ?
C26 C25 C30 C29 0.0(6) . . . . ?
N1 C25 C30 C29 -179.5(4) . . . . ?
C28 C29 C30 C25 -1.0(7) . . . . ?
O1 S1 C31 C36 -15.5(4) . . . . ?
O2 S1 C31 C36 -145.4(3) . . . . ?
N2 S1 C31 C36 101.8(3) . . . . ?
O1 S1 C31 C32 163.5(3) . . . . ?
O2 S1 C31 C32 33.6(4) . . . . ?
N2 S1 C31 C32 -79.3(3) . . . . ?
C36 C31 C32 C33 2.0(6) . . . . ?
S1 C31 C32 C33 -176.9(3) . . . . ?
C31 C32 C33 C34 -0.7(7) . . . . ?
C32 C33 C34 C35 -1.1(8) . . . . ?
C32 C33 C34 C37 -179.6(5) . . . . ?
C33 C34 C35 C36 1.6(7) . . . . ?
C37 C34 C35 C36 -179.9(5) . . . . ?
C32 C31 C36 C35 -1.6(6) . . . . ?
S1 C31 C36 C35 177.4(3) . . . . ?
C34 C35 C36 C31 -0.2(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.811(18) 2.15(2) 2.953(4) 171(3) 2_566
N2 H2 O2 0.811(18) 2.15(2) 2.953(4) 171(3) 2_566

_refine_diff_density_max         0.628
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 988137'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cd212405

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H44 N2 O Si2'
_chemical_formula_weight         516.86

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.3200(9)
_cell_length_b                   12.6141(10)
_cell_length_c                   21.9831(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.771(2)
_cell_angle_gamma                90.00
_cell_volume                     3408.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2917
_cell_measurement_theta_min      4.628
_cell_measurement_theta_max      50.983

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.134
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.007
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.66837
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6711
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6711
_reflns_number_gt                4307
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0744P)²+0.0000P] 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         6711
_refine_ls_number_parameters     336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1446
_refine_ls_wR_factor_gt          0.1329
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.500 208 42 ' '
2 0.000 0.500 1.000 208 42 ' '
_platon_squeeze_details          
;
;



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
Si1 Si 0.64206(5) -0.16193(5) 0.21720(3) 0.05527(19) Uani 1 1 d . . .
Si2 Si 0.19475(5) -0.07004(5) 0.12326(3) 0.05383(19) Uani 1 1 d . . .
N1 N 0.44699(12) 0.11450(11) 0.07514(7) 0.0437(4) Uani 1 1 d . . .
N2 N 0.16369(14) 0.16300(14) 0.03956(9) 0.0684(5) Uani 1 1 d . . .
H2A H 0.1575 0.2194 0.0176 0.082 Uiso 1 1 calc R . .
H2B H 0.1065 0.1291 0.0488 0.082 Uiso 1 1 calc R . .
O1 O 0.89360(11) 0.18414(13) 0.08227(8) 0.0729(5) Uani 1 1 d . . .
C1 C 0.40195(15) 0.03046(14) 0.10483(8) 0.0440(5) Uani 1 1 d . . .
C2 C 0.28899(15) 0.03348(15) 0.09626(8) 0.0458(5) Uani 1 1 d . . .
C3 C 0.26732(15) 0.12628(15) 0.06032(9) 0.0473(5) Uani 1 1 d . . .
C4 C 0.36336(15) 0.17498(14) 0.04792(8) 0.0455(5) Uani 1 1 d . . .
C5 C 0.38152(16) 0.26837(15) 0.00957(8) 0.0475(5) Uani 1 1 d . . .
C6 C 0.31909(19) 0.35900(16) 0.01465(10) 0.0642(6) Uani 1 1 d . . .
H6 H 0.2659 0.3613 0.0427 0.077 Uiso 1 1 calc R . .
C7 C 0.3357(2) 0.44640(19) -0.02204(13) 0.0828(8) Uani 1 1 d . . .
H7 H 0.2938 0.5071 -0.0181 0.099 Uiso 1 1 calc R . .
C8 C 0.4125(2) 0.4440(2) -0.06359(13) 0.0842(8) Uani 1 1 d . . .
H8 H 0.4228 0.5027 -0.0881 0.101 Uiso 1 1 calc R . .
C9 C 0.4747(2) 0.3550(2) -0.06942(11) 0.0729(7) Uani 1 1 d . . .
H9 H 0.5276 0.3536 -0.0977 0.088 Uiso 1 1 calc R . .
C10 C 0.45927(17) 0.26796(17) -0.03354(9) 0.0571(5) Uani 1 1 d . . .
H10 H 0.5015 0.2077 -0.0381 0.068 Uiso 1 1 calc R . .
C11 C 0.56095(15) 0.13626(14) 0.07658(8) 0.0422(4) Uani 1 1 d . . .
C12 C 0.60258(17) 0.22961(16) 0.10045(9) 0.0546(5) Uani 1 1 d . . .
H12 H 0.5558 0.2800 0.1151 0.066 Uiso 1 1 calc R . .
C13 C 0.71347(17) 0.24949(16) 0.10291(10) 0.0572(5) Uani 1 1 d . . .
H13 H 0.7410 0.3133 0.1185 0.069 Uiso 1 1 calc R . .
C14 C 0.78277(16) 0.17315(17) 0.08190(9) 0.0524(5) Uani 1 1 d . . .
C15 C 0.74065(16) 0.07964(17) 0.05821(9) 0.0538(5) Uani 1 1 d . . .
H15 H 0.7871 0.0282 0.0443 0.065 Uiso 1 1 calc R . .
C16 C 0.63108(16) 0.06193(16) 0.05504(9) 0.0508(5) Uani 1 1 d . . .
H16 H 0.6034 -0.0009 0.0382 0.061 Uiso 1 1 calc R . .
C17 C 0.9407(2) 0.2736(2) 0.11094(15) 0.1089(11) Uani 1 1 d . . .
H17A H 0.9150 0.3363 0.0899 0.163 Uiso 1 1 calc R . .
H17B H 1.0184 0.2696 0.1102 0.163 Uiso 1 1 calc R . .
H17C H 0.9211 0.2763 0.1524 0.163 Uiso 1 1 calc R . .
C18 C 0.47200(16) -0.03796(15) 0.14101(9) 0.0482(5) Uani 1 1 d . . .
C19 C 0.53678(17) -0.09077(16) 0.17089(10) 0.0554(5) Uani 1 1 d . . .
C20 C 0.7472(2) -0.2076(2) 0.16654(12) 0.0835(8) Uani 1 1 d . . .
H20A H 0.7166 -0.2605 0.1391 0.125 Uiso 1 1 calc R . .
H20B H 0.8074 -0.2373 0.1907 0.125 Uiso 1 1 calc R . .
H20C H 0.7719 -0.1486 0.1436 0.125 Uiso 1 1 calc R . .
C21 C 0.5751(2) -0.2743(2) 0.25414(13) 0.0911(9) Uani 1 1 d . . .
H21A H 0.5105 -0.2495 0.2718 0.137 Uiso 1 1 calc R . .
H21B H 0.6241 -0.3036 0.2855 0.137 Uiso 1 1 calc R . .
H21C H 0.5561 -0.3278 0.2243 0.137 Uiso 1 1 calc R . .
C22 C 0.70283(19) -0.06558(18) 0.27499(10) 0.0637(6) Uani 1 1 d . . .
C23 C 0.6151(3) -0.0287(2) 0.31680(13) 0.1007(9) Uani 1 1 d . . .
H23A H 0.6442 0.0262 0.3434 0.151 Uiso 1 1 calc R . .
H23B H 0.5926 -0.0874 0.3407 0.151 Uiso 1 1 calc R . .
H23C H 0.5537 -0.0018 0.2924 0.151 Uiso 1 1 calc R . .
C24 C 0.7952(2) -0.1194(2) 0.31389(12) 0.0877(8) Uani 1 1 d . . .
H24A H 0.8509 -0.1417 0.2881 0.132 Uiso 1 1 calc R . .
H24B H 0.7670 -0.1800 0.3341 0.132 Uiso 1 1 calc R . .
H24C H 0.8253 -0.0702 0.3437 0.132 Uiso 1 1 calc R . .
C25 C 0.7481(3) 0.0305(2) 0.24270(14) 0.1053(10) Uani 1 1 d . . .
H25A H 0.6895 0.0680 0.2213 0.158 Uiso 1 1 calc R . .
H25B H 0.7989 0.0072 0.2142 0.158 Uiso 1 1 calc R . .
H25C H 0.7843 0.0766 0.2723 0.158 Uiso 1 1 calc R . .
C26 C 0.2594(2) -0.20281(18) 0.11694(13) 0.0823(8) Uani 1 1 d . . .
H26A H 0.2733 -0.2162 0.0752 0.124 Uiso 1 1 calc R . .
H26B H 0.2116 -0.2563 0.1309 0.124 Uiso 1 1 calc R . .
H26C H 0.3268 -0.2043 0.1415 0.124 Uiso 1 1 calc R . .
C27 C 0.06432(18) -0.07311(19) 0.07454(10) 0.0707(7) Uani 1 1 d . . .
H27A H 0.0245 -0.0088 0.0803 0.106 Uiso 1 1 calc R . .
H27B H 0.0216 -0.1327 0.0858 0.106 Uiso 1 1 calc R . .
H27C H 0.0800 -0.0793 0.0325 0.106 Uiso 1 1 calc R . .
C28 C 0.1605(2) -0.0429(2) 0.20398(11) 0.0728(7) Uani 1 1 d . . .
C29 C 0.1107(3) 0.0677(3) 0.20787(14) 0.1061(10) Uani 1 1 d . . .
H29A H 0.0904 0.0803 0.2487 0.159 Uiso 1 1 calc R . .
H29B H 0.0474 0.0724 0.1801 0.159 Uiso 1 1 calc R . .
H29C H 0.1630 0.1198 0.1973 0.159 Uiso 1 1 calc R . .
C30 C 0.0758(3) -0.1239(3) 0.22363(14) 0.1202(12) Uani 1 1 d . . .
H30A H 0.1065 -0.1939 0.2234 0.180 Uiso 1 1 calc R . .
H30B H 0.0125 -0.1212 0.1957 0.180 Uiso 1 1 calc R . .
H30C H 0.0556 -0.1071 0.2640 0.180 Uiso 1 1 calc R . .
C31 C 0.2610(2) -0.0496(3) 0.24842(12) 0.1017(10) Uani 1 1 d . . .
H31A H 0.2412 -0.0323 0.2888 0.153 Uiso 1 1 calc R . .
H31B H 0.3149 -0.0004 0.2363 0.153 Uiso 1 1 calc R . .
H31C H 0.2900 -0.1202 0.2481 0.153 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
Si1 C19 1.830(2) . ?
Si1 C21 1.853(3) . ?
Si1 C20 1.854(3) . ?
Si1 C22 1.878(2) . ?
Si2 C26 1.864(2) . ?
Si2 C2 1.870(2) . ?
Si2 C27 1.872(2) . ?
Si2 C28 1.882(3) . ?
N1 C1 1.380(2) . ?
N1 C4 1.386(2) . ?
N1 C11 1.429(2) . ?
N2 C3 1.406(2) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
O1 C14 1.372(2) . ?
O1 C17 1.400(3) . ?
C1 C2 1.392(3) . ?
C1 C18 1.425(3) . ?
C2 C3 1.428(3) . ?
C3 C4 1.376(3) . ?
C4 C5 1.474(3) . ?
C5 C6 1.387(3) . ?
C5 C10 1.391(3) . ?
C6 C7 1.389(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.358(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.370(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.375(3) . ?
C11 C16 1.380(3) . ?
C12 C13 1.387(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(3) . ?
C15 C16 1.365(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.201(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C25 1.528(3) . ?
C22 C24 1.536(3) . ?
C22 C23 1.536(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C31 1.528(3) . ?
C28 C29 1.529(4) . ?
C28 C30 1.542(4) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 Si1 C21 107.41(11) . . ?
C19 Si1 C20 108.39(11) . . ?
C21 Si1 C20 111.97(13) . . ?
C19 Si1 C22 107.17(10) . . ?
C21 Si1 C22 111.55(12) . . ?
C20 Si1 C22 110.14(11) . . ?
C26 Si2 C2 109.04(11) . . ?
C26 Si2 C27 107.10(11) . . ?
C2 Si2 C27 111.13(9) . . ?
C26 Si2 C28 110.92(13) . . ?
C2 Si2 C28 110.79(10) . . ?
C27 Si2 C28 107.80(11) . . ?
C1 N1 C4 108.45(14) . . ?
C1 N1 C11 124.20(14) . . ?
C4 N1 C11 127.24(15) . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C14 O1 C17 117.85(18) . . ?
N1 C1 C2 110.14(15) . . ?
N1 C1 C18 118.77(16) . . ?
C2 C1 C18 130.92(17) . . ?
C1 C2 C3 104.25(16) . . ?
C1 C2 Si2 125.02(14) . . ?
C3 C2 Si2 130.60(14) . . ?
C4 C3 N2 124.25(17) . . ?
C4 C3 C2 110.10(16) . . ?
N2 C3 C2 125.64(18) . . ?
C3 C4 N1 107.04(16) . . ?
C3 C4 C5 129.40(17) . . ?
N1 C4 C5 123.39(17) . . ?
C6 C5 C10 117.93(19) . . ?
C6 C5 C4 120.46(19) . . ?
C10 C5 C4 121.60(18) . . ?
C5 C6 C7 120.3(2) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.0(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 121.1(2) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C12 C11 C16 119.13(18) . . ?
C12 C11 N1 120.95(18) . . ?
C16 C11 N1 119.90(16) . . ?
C11 C12 C13 120.77(19) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.23(18) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
O1 C14 C15 116.03(19) . . ?
O1 C14 C13 124.23(18) . . ?
C15 C14 C13 119.73(18) . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 120.71(18) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C1 175.5(2) . . ?
C18 C19 Si1 175.52(19) . . ?
Si1 C20 H20A 109.5 . . ?
Si1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Si1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Si1 C21 H21A 109.5 . . ?
Si1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
Si1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C25 C22 C24 109.3(2) . . ?
C25 C22 C23 109.3(2) . . ?
C24 C22 C23 109.0(2) . . ?
C25 C22 Si1 109.89(17) . . ?
C24 C22 Si1 109.76(16) . . ?
C23 C22 Si1 109.63(17) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
Si2 C26 H26A 109.5 . . ?
Si2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
Si2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
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 . . ?
C31 C28 C29 109.0(2) . . ?
C31 C28 C30 108.6(2) . . ?
C29 C28 C30 107.9(3) . . ?
C31 C28 Si2 111.71(19) . . ?
C29 C28 Si2 109.52(17) . . ?
C30 C28 Si2 109.98(19) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
C4 N1 C1 C2 1.4(2) . . . . ?
C11 N1 C1 C2 177.86(16) . . . . ?
C4 N1 C1 C18 -174.42(16) . . . . ?
C11 N1 C1 C18 2.1(3) . . . . ?
N1 C1 C2 C3 -1.1(2) . . . . ?
C18 C1 C2 C3 173.99(19) . . . . ?
N1 C1 C2 Si2 175.21(13) . . . . ?
C18 C1 C2 Si2 -9.7(3) . . . . ?
C26 Si2 C2 C1 -35.5(2) . . . . ?
C27 Si2 C2 C1 -153.33(17) . . . . ?
C28 Si2 C2 C1 86.85(19) . . . . ?
C26 Si2 C2 C3 139.84(19) . . . . ?
C27 Si2 C2 C3 22.0(2) . . . . ?
C28 Si2 C2 C3 -97.8(2) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
Si2 C2 C3 C4 -175.56(15) . . . . ?
C1 C2 C3 N2 179.75(19) . . . . ?
Si2 C2 C3 N2 3.7(3) . . . . ?
N2 C3 C4 N1 -178.95(18) . . . . ?
C2 C3 C4 N1 0.3(2) . . . . ?
N2 C3 C4 C5 -3.5(3) . . . . ?
C2 C3 C4 C5 175.74(18) . . . . ?
C1 N1 C4 C3 -1.0(2) . . . . ?
C11 N1 C4 C3 -177.36(17) . . . . ?
C1 N1 C4 C5 -176.79(17) . . . . ?
C11 N1 C4 C5 6.9(3) . . . . ?
C3 C4 C5 C6 46.5(3) . . . . ?
N1 C4 C5 C6 -138.7(2) . . . . ?
C3 C4 C5 C10 -132.0(2) . . . . ?
N1 C4 C5 C10 42.8(3) . . . . ?
C10 C5 C6 C7 -0.7(3) . . . . ?
C4 C5 C6 C7 -179.3(2) . . . . ?
C5 C6 C7 C8 0.5(4) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C8 C9 C10 C5 -0.6(3) . . . . ?
C6 C5 C10 C9 0.8(3) . . . . ?
C4 C5 C10 C9 179.35(19) . . . . ?
C1 N1 C11 C12 -118.6(2) . . . . ?
C4 N1 C11 C12 57.2(3) . . . . ?
C1 N1 C11 C16 59.9(2) . . . . ?
C4 N1 C11 C16 -124.3(2) . . . . ?
C16 C11 C12 C13 0.1(3) . . . . ?
N1 C11 C12 C13 178.65(18) . . . . ?
C11 C12 C13 C14 -1.1(3) . . . . ?
C17 O1 C14 C15 -174.3(2) . . . . ?
C17 O1 C14 C13 6.4(3) . . . . ?
C12 C13 C14 O1 -179.8(2) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
O1 C14 C15 C16 -179.04(19) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C11 -1.3(3) . . . . ?
C12 C11 C16 C15 1.1(3) . . . . ?
N1 C11 C16 C15 -177.46(17) . . . . ?
N1 C1 C18 C19 8(3) . . . . ?
C2 C1 C18 C19 -167(3) . . . . ?
C1 C18 C19 Si1 21(5) . . . . ?
C21 Si1 C19 C18 153(3) . . . . ?
C20 Si1 C19 C18 -86(3) . . . . ?
C22 Si1 C19 C18 33(3) . . . . ?
C19 Si1 C22 C25 -57.6(2) . . . . ?
C21 Si1 C22 C25 -174.94(19) . . . . ?
C20 Si1 C22 C25 60.1(2) . . . . ?
C19 Si1 C22 C24 -177.83(17) . . . . ?
C21 Si1 C22 C24 64.9(2) . . . . ?
C20 Si1 C22 C24 -60.1(2) . . . . ?
C19 Si1 C22 C23 62.49(19) . . . . ?
C21 Si1 C22 C23 -54.8(2) . . . . ?
C20 Si1 C22 C23 -179.80(18) . . . . ?
C26 Si2 C28 C31 57.5(2) . . . . ?
C2 Si2 C28 C31 -63.7(2) . . . . ?
C27 Si2 C28 C31 174.46(19) . . . . ?
C26 Si2 C28 C29 178.34(18) . . . . ?
C2 Si2 C28 C29 57.1(2) . . . . ?
C27 Si2 C28 C29 -64.7(2) . . . . ?
C26 Si2 C28 C30 -63.2(2) . . . . ?
C2 Si2 C28 C30 175.56(19) . . . . ?
C27 Si2 C28 C30 53.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 988138'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cd212665

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 N2'
_chemical_formula_weight         206.24

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.876(4)
_cell_length_b                   7.462(3)
_cell_length_c                   24.973(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2213.2(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2048
_cell_measurement_theta_min      4.760
_cell_measurement_theta_max      44.527

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.034
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.09093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12431
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2181
_reflns_number_gt                1533
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0677P)²+0.3721P] 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         2181
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1549
_refine_ls_wR_factor_gt          0.1394
_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
N1 N 0.55742(13) 0.2424(2) 0.60260(6) 0.0660(5) Uani 1 1 d . . .
N2 N 0.29470(16) 0.4193(3) 0.63164(7) 0.0866(6) Uani 1 1 d . . .
C1 C 0.50270(19) 0.1537(3) 0.69364(8) 0.0725(6) Uani 1 1 d . . .
H1 H 0.4372 0.1001 0.6810 0.087 Uiso 1 1 calc R . .
C2 C 0.5287(2) 0.1460(3) 0.74722(9) 0.0806(7) Uani 1 1 d . . .
H2 H 0.4808 0.0862 0.7706 0.097 Uiso 1 1 calc R . .
C3 C 0.6240(2) 0.2251(3) 0.76638(9) 0.0795(6) Uani 1 1 d . . .
H3 H 0.6406 0.2203 0.8027 0.095 Uiso 1 1 calc R . .
C4 C 0.69518(18) 0.3115(3) 0.73193(9) 0.0752(6) Uani 1 1 d . . .
H4 H 0.7599 0.3664 0.7450 0.090 Uiso 1 1 calc R . .
C5 C 0.67171(16) 0.3179(3) 0.67803(9) 0.0692(6) Uani 1 1 d . . .
H5 H 0.7215 0.3739 0.6547 0.083 Uiso 1 1 calc R . .
C6 C 0.57390(16) 0.2409(3) 0.65869(8) 0.0621(5) Uani 1 1 d . . .
C7 C 0.46578(15) 0.2879(3) 0.58055(7) 0.0591(5) Uani 1 1 d . . .
C8 C 0.37026(17) 0.3582(3) 0.61047(7) 0.0637(5) Uani 1 1 d . . .
C9 C 0.45122(15) 0.2786(3) 0.52175(7) 0.0599(5) Uani 1 1 d . . .
C10 C 0.53774(17) 0.2177(3) 0.48996(8) 0.0767(6) Uani 1 1 d . . .
H10 H 0.6050 0.1816 0.5057 0.092 Uiso 1 1 calc R . .
C11 C 0.52614(19) 0.2097(4) 0.43551(9) 0.0807(7) Uani 1 1 d . . .
H11 H 0.5857 0.1694 0.4145 0.097 Uiso 1 1 calc R . .
C12 C 0.42828(19) 0.2603(4) 0.41194(9) 0.0821(7) Uani 1 1 d . . .
H12 H 0.4203 0.2527 0.3750 0.099 Uiso 1 1 calc R . .
C13 C 0.3418(2) 0.3221(4) 0.44251(9) 0.0948(8) Uani 1 1 d . . .
H13 H 0.2748 0.3578 0.4264 0.114 Uiso 1 1 calc R . .
C14 C 0.35335(17) 0.3319(4) 0.49738(8) 0.0807(7) Uani 1 1 d . . .
H14 H 0.2941 0.3751 0.5181 0.097 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
N1 C7 1.266(2) . ?
N1 C6 1.414(3) . ?
N2 C8 1.137(2) . ?
C1 C2 1.375(3) . ?
C1 C6 1.379(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.363(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C7 C8 1.456(3) . ?
C7 C9 1.480(3) . ?
C9 C14 1.371(3) . ?
C9 C10 1.376(3) . ?
C10 C11 1.368(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.356(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

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 N1 C6 123.48(17) . . ?
C2 C1 C6 119.9(2) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.36(19) . . ?
C1 C6 N1 123.08(17) . . ?
C5 C6 N1 117.31(18) . . ?
N1 C7 C8 122.91(18) . . ?
N1 C7 C9 121.28(17) . . ?
C8 C7 C9 115.78(17) . . ?
N2 C8 C7 176.3(2) . . ?
C14 C9 C10 118.21(19) . . ?
C14 C9 C7 121.73(17) . . ?
C10 C9 C7 120.05(17) . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 120.7(2) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?

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
C6 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 1.9(3) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C2 C1 C6 N1 174.9(2) . . . . ?
C4 C5 C6 C1 -2.0(3) . . . . ?
C4 C5 C6 N1 -176.40(18) . . . . ?
C7 N1 C6 C1 52.4(3) . . . . ?
C7 N1 C6 C5 -133.4(2) . . . . ?
C6 N1 C7 C8 5.3(3) . . . . ?
C6 N1 C7 C9 -176.97(18) . . . . ?
N1 C7 C8 N2 141(3) . . . . ?
C9 C7 C8 N2 -37(3) . . . . ?
N1 C7 C9 C14 -178.3(2) . . . . ?
C8 C7 C9 C14 -0.5(3) . . . . ?
N1 C7 C9 C10 0.7(3) . . . . ?
C8 C7 C9 C10 178.6(2) . . . . ?
C14 C9 C10 C11 -0.4(3) . . . . ?
C7 C9 C10 C11 -179.4(2) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C10 C11 C12 C13 1.1(4) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C10 C9 C14 C13 0.9(4) . . . . ?
C7 C9 C14 C13 179.9(2) . . . . ?
C12 C13 C14 C9 -0.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.030
_database_code_depnum_ccdc_archive 'CCDC 988139'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cd213419

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H47 Br N2 O3 Si2'
_chemical_formula_weight         655.82

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                   12.938(4)
_cell_length_b                   17.204(5)
_cell_length_c                   18.135(6)
_cell_angle_alpha                82.713(5)
_cell_angle_beta                 85.701(4)
_cell_angle_gamma                70.712(4)
_cell_volume                     3777(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1109
_cell_measurement_theta_min      4.812
_cell_measurement_theta_max      56.387

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.134
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1384
_exptl_absorpt_coefficient_mu    1.183
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2563
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21502
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_av_sigmaI/netI    0.2587
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         25.50
_reflns_number_total             13970
_reflns_number_gt                4191
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1399P)²+0.0000P] 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         13970
_refine_ls_number_parameters     898
_refine_ls_number_restraints     186
_refine_ls_R_factor_all          0.2878
_refine_ls_R_factor_gt           0.0926
_refine_ls_wR_factor_ref         0.3316
_refine_ls_wR_factor_gt          0.2264
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_restrained_S_all      0.934
_refine_ls_shift/su_max          0.023
_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 0.54014(17) 0.84508(17) 1.03652(9) 0.2073(11) Uani 1 1 d . . .
Br2 Br 0.85023(10) 0.14933(7) 0.41134(8) 0.1142(6) Uani 1 1 d . . .
Si1 Si 0.7140(2) 1.03757(19) 0.77397(16) 0.0787(9) Uani 1 1 d . . .
Si2 Si 1.1784(2) 0.9394(3) 0.83987(19) 0.1083(13) Uani 1 1 d . . .
N1 N 0.6420(6) 0.9414(5) 0.6646(4) 0.086(3) Uani 1 1 d . . .
H1 H 0.5816 0.9719 0.6446 0.103 Uiso 1 1 calc R . .
N2 N 0.7701(6) 0.7497(5) 0.7419(5) 0.074(2) Uani 1 1 d . . .
N3 N 0.8285(6) 0.5692(4) 0.3537(4) 0.071(2) Uani 1 1 d . . .
H3 H 0.8914 0.5759 0.3447 0.085 Uiso 1 1 calc R . .
N4 N 0.6758(5) 0.5038(5) 0.4882(4) 0.0553(18) Uani 1 1 d . . .
O1 O 0.8906(5) 0.8569(4) 0.4258(3) 0.0771(18) Uani 1 1 d . . .
O2 O 0.9259(5) 0.6957(4) 0.4084(3) 0.0753(18) Uani 1 1 d . . .
O3 O 0.9056(4) 0.5884(4) 0.5199(3) 0.0604(15) Uani 1 1 d . . .
O4 O 0.6156(5) 0.8671(4) 0.4121(4) 0.0786(18) Uani 1 1 d . . .
O5 O 0.5412(4) 0.8783(4) 0.5522(3) 0.0753(18) Uani 1 1 d . . .
O6 O 0.5209(5) 0.7494(4) 0.6393(4) 0.0789(18) Uani 1 1 d . . .
C1 C 0.7743(6) 0.8045(6) 0.6885(6) 0.060(2) Uani 1 1 d . . .
C2 C 0.7306(7) 0.8967(6) 0.6939(5) 0.057(2) Uani 1 1 d . . .
C3 C 0.7921(7) 0.9357(5) 0.7376(4) 0.062(2) Uani 1 1 d . . .
C4 C 0.9007(7) 0.8939(6) 0.7435(5) 0.079(3) Uani 1 1 d . . .
H4 H 0.9265 0.8439 0.7230 0.095 Uiso 1 1 calc R . .
C5 C 0.9789(7) 0.9173(7) 0.7769(6) 0.089(3) Uani 1 1 d . . .
C6 C 1.0536(9) 0.9296(8) 0.8013(6) 0.108(4) Uani 1 1 d . . .
C7 C 0.8187(6) 0.7771(6) 0.6156(5) 0.053(2) Uani 1 1 d . . .
C8 C 0.8364(6) 0.8326(6) 0.5578(5) 0.064(2) Uani 1 1 d . . .
H8 H 0.8234 0.8874 0.5660 0.077 Uiso 1 1 calc R . .
C9 C 0.8739(6) 0.8074(6) 0.4868(6) 0.062(2) Uani 1 1 d . . .
C10 C 0.8943(6) 0.7237(6) 0.4763(5) 0.055(2) Uani 1 1 d . . .
C11 C 0.8796(6) 0.6684(6) 0.5355(5) 0.054(2) Uani 1 1 d . . .
C12 C 0.8414(6) 0.6953(5) 0.6044(5) 0.051(2) Uani 1 1 d . . .
H12 H 0.8310 0.6578 0.6434 0.062 Uiso 1 1 calc R . .
C13 C 0.7165(10) 0.7754(6) 0.8100(6) 0.079(3) Uani 1 1 d . . .
C14 C 0.6073(10) 0.8065(8) 0.8184(7) 0.112(4) Uani 1 1 d . . .
H14 H 0.5645 0.8163 0.7771 0.135 Uiso 1 1 calc R . .
C15 C 0.5571(12) 0.8242(9) 0.8868(9) 0.132(5) Uani 1 1 d . . .
H15 H 0.4809 0.8425 0.8902 0.158 Uiso 1 1 calc R . .
C16 C 0.6089(14) 0.8169(11) 0.9455(8) 0.131(6) Uani 1 1 d . . .
C17 C 0.7198(15) 0.7851(11) 0.9412(7) 0.153(6) Uani 1 1 d . . .
H17 H 0.7589 0.7791 0.9837 0.184 Uiso 1 1 calc R . .
C18 C 0.7803(12) 0.7599(10) 0.8713(8) 0.143(5) Uani 1 1 d . . .
H18 H 0.8561 0.7354 0.8687 0.171 Uiso 1 1 calc R . .
C19 C 0.8793(8) 0.9400(6) 0.4352(6) 0.097(3) Uani 1 1 d . . .
H19A H 0.8040 0.9695 0.4470 0.146 Uiso 1 1 calc R . .
H19B H 0.9021 0.9663 0.3900 0.146 Uiso 1 1 calc R . .
H19C H 0.9240 0.9406 0.4749 0.146 Uiso 1 1 calc R . .
C20 C 1.0268(9) 0.7045(7) 0.3724(5) 0.100(4) Uani 1 1 d . . .
H20A H 1.0095 0.7533 0.3372 0.150 Uiso 1 1 calc R . .
H20B H 1.0642 0.6567 0.3470 0.150 Uiso 1 1 calc R . .
H20C H 1.0732 0.7094 0.4093 0.150 Uiso 1 1 calc R . .
C21 C 0.8946(7) 0.5288(6) 0.5803(5) 0.072(3) Uani 1 1 d . . .
H21A H 0.9331 0.5329 0.6221 0.107 Uiso 1 1 calc R . .
H21B H 0.9249 0.4740 0.5650 0.107 Uiso 1 1 calc R . .
H21C H 0.8185 0.5395 0.5941 0.107 Uiso 1 1 calc R . .
C22 C 0.5707(7) 1.0428(7) 0.8014(6) 0.103(4) Uani 1 1 d . . .
H22A H 0.5340 1.0933 0.8232 0.154 Uiso 1 1 calc R . .
H22B H 0.5711 0.9964 0.8370 0.154 Uiso 1 1 calc R . .
H22C H 0.5328 1.0416 0.7583 0.154 Uiso 1 1 calc R . .
C23 C 0.7765(9) 1.0435(8) 0.8614(6) 0.137(5) Uani 1 1 d . . .
H23A H 0.8522 1.0387 0.8516 0.205 Uiso 1 1 calc R . .
H23B H 0.7712 0.9992 0.8979 0.205 Uiso 1 1 calc R . .
H23C H 0.7383 1.0957 0.8800 0.205 Uiso 1 1 calc R . .
C24 C 0.7185(11) 1.1248(7) 0.7035(8) 0.117(4) Uani 1 1 d . . .
C25 C 0.6366(18) 1.2084(10) 0.7357(13) 0.279(12) Uani 1 1 d . . .
H25A H 0.6649 1.2165 0.7805 0.418 Uiso 1 1 calc R . .
H25B H 0.5653 1.2029 0.7462 0.418 Uiso 1 1 calc R . .
H25C H 0.6311 1.2552 0.6993 0.418 Uiso 1 1 calc R . .
C26 C 0.8282(13) 1.1303(12) 0.6877(12) 0.255(12) Uani 1 1 d . . .
H26A H 0.8759 1.0790 0.6716 0.383 Uiso 1 1 calc R . .
H26B H 0.8556 1.1408 0.7318 0.383 Uiso 1 1 calc R . .
H26C H 0.8253 1.1746 0.6491 0.383 Uiso 1 1 calc R . .
C27 C 0.6651(13) 1.1254(10) 0.6311(8) 0.185(8) Uani 1 1 d . . .
H27A H 0.6509 1.1787 0.6029 0.277 Uiso 1 1 calc R . .
H27B H 0.5974 1.1141 0.6423 0.277 Uiso 1 1 calc R . .
H27C H 0.7134 1.0836 0.6027 0.277 Uiso 1 1 calc R . .
C28 C 1.2140(11) 0.8616(10) 0.9208(8) 0.183(7) Uani 1 1 d . . .
H28A H 1.2745 0.8671 0.9448 0.275 Uiso 1 1 calc R . .
H28B H 1.2342 0.8072 0.9049 0.275 Uiso 1 1 calc R . .
H28C H 1.1521 0.8696 0.9551 0.275 Uiso 1 1 calc R . .
C29 C 1.2845(9) 0.9171(9) 0.7633(7) 0.147(6) Uani 1 1 d . . .
H29A H 1.2605 0.9572 0.7210 0.220 Uiso 1 1 calc R . .
H29B H 1.2959 0.8626 0.7497 0.220 Uiso 1 1 calc R . .
H29C H 1.3520 0.9199 0.7796 0.220 Uiso 1 1 calc R . .
C30 C 1.1521(10) 1.0455(10) 0.8657(8) 0.118(4) Uani 1 1 d . . .
C31 C 1.0684(10) 1.0639(11) 0.9278(7) 0.165(7) Uani 1 1 d . . .
H31A H 1.0767 1.0145 0.9612 0.248 Uiso 1 1 calc R . .
H31B H 0.9965 1.0832 0.9080 0.248 Uiso 1 1 calc R . .
H31C H 1.0783 1.1059 0.9541 0.248 Uiso 1 1 calc R . .
C32 C 1.2603(11) 1.0543(11) 0.8857(9) 0.182(7) Uani 1 1 d . . .
H32A H 1.2471 1.1089 0.8996 0.273 Uiso 1 1 calc R . .
H32B H 1.3106 1.0457 0.8435 0.273 Uiso 1 1 calc R . .
H32C H 1.2910 1.0139 0.9266 0.273 Uiso 1 1 calc R . .
C33 C 1.1064(13) 1.1089(11) 0.7968(9) 0.168(6) Uani 1 1 d . . .
H33A H 1.0352 1.1078 0.7866 0.252 Uiso 1 1 calc R . .
H33B H 1.1549 1.0942 0.7544 0.252 Uiso 1 1 calc R . .
H33C H 1.1011 1.1635 0.8070 0.252 Uiso 1 1 calc R . .
C34 C 0.6810(6) 0.5659(6) 0.4436(5) 0.057(2) Uani 1 1 d . . .
C35 C 0.7368(7) 0.5595(5) 0.3669(5) 0.060(2) Uani 1 1 d . A .
C36 C 0.6776(8) 0.5430(6) 0.3052(5) 0.069(3) Uani 1 1 d . . .
C37 C 0.5736(8) 0.5491(6) 0.3164(5) 0.072(3) Uani 1 1 d . A .
H37 H 0.5443 0.5604 0.3638 0.087 Uiso 1 1 calc R . .
C38 C 0.4988(8) 0.5405(7) 0.2652(6) 0.083(3) Uani 1 1 d . . .
C39 C 0.4308(9) 0.5379(7) 0.2234(6) 0.099(4) Uani 1 1 d . A .
C40 C 0.6433(6) 0.6491(5) 0.4706(5) 0.051(2) Uani 1 1 d . . .
C41 C 0.6467(6) 0.7184(5) 0.4237(5) 0.058(2) Uani 1 1 d . . .
H41 H 0.6714 0.7141 0.3744 0.069 Uiso 1 1 calc R . .
C42 C 0.6117(6) 0.7957(6) 0.4528(6) 0.060(2) Uani 1 1 d . . .
C43 C 0.5693(6) 0.8031(6) 0.5248(6) 0.057(2) Uani 1 1 d . . .
C44 C 0.5636(7) 0.7340(7) 0.5706(5) 0.062(2) Uani 1 1 d . . .
C45 C 0.5998(6) 0.6577(5) 0.5444(5) 0.057(2) Uani 1 1 d . . .
H45 H 0.5959 0.6112 0.5753 0.069 Uiso 1 1 calc R . .
C46 C 0.7187(7) 0.4215(5) 0.4687(4) 0.053(2) Uani 1 1 d . . .
C47 C 0.6518(7) 0.3718(6) 0.4781(5) 0.073(3) Uani 1 1 d . . .
H47 H 0.5796 0.3934 0.4953 0.087 Uiso 1 1 calc R . .
C48 C 0.6919(8) 0.2910(6) 0.4620(5) 0.074(3) Uani 1 1 d . . .
H48 H 0.6469 0.2581 0.4687 0.089 Uiso 1 1 calc R . .
C49 C 0.7960(8) 0.2596(6) 0.4365(5) 0.067(3) Uani 1 1 d . . .
C50 C 0.8659(7) 0.3043(5) 0.4286(5) 0.071(3) Uani 1 1 d . . .
H50 H 0.9387 0.2810 0.4133 0.085 Uiso 1 1 calc R . .
C51 C 0.8246(7) 0.3869(5) 0.4444(5) 0.066(3) Uani 1 1 d . . .
H51 H 0.8706 0.4190 0.4381 0.079 Uiso 1 1 calc R . .
C52 C 0.6633(8) 0.8610(6) 0.3397(6) 0.089(3) Uani 1 1 d . . .
H52A H 0.7377 0.8246 0.3422 0.133 Uiso 1 1 calc R . .
H52B H 0.6621 0.9148 0.3172 0.133 Uiso 1 1 calc R . .
H52C H 0.6226 0.8392 0.3104 0.133 Uiso 1 1 calc R . .
C53 C 0.4285(7) 0.9285(6) 0.5446(6) 0.091(3) Uani 1 1 d . . .
H53A H 0.4109 0.9381 0.4930 0.136 Uiso 1 1 calc R . .
H53B H 0.4167 0.9806 0.5634 0.136 Uiso 1 1 calc R . .
H53C H 0.3825 0.9004 0.5722 0.136 Uiso 1 1 calc R . .
C54 C 0.5089(11) 0.6822(8) 0.6880(6) 0.121(4) Uani 1 1 d . . .
H54A H 0.4696 0.6543 0.6642 0.182 Uiso 1 1 calc R . .
H54B H 0.4690 0.7021 0.7324 0.182 Uiso 1 1 calc R . .
H54C H 0.5800 0.6442 0.7008 0.182 Uiso 1 1 calc R . .
Si3 Si 0.7715(8) 0.4929(6) 0.2254(5) 0.079(3) Uani 0.50 1 d PDU A 1
Si4 Si 0.3274(7) 0.5195(5) 0.1694(4) 0.078(2) Uani 0.50 1 d PU A 1
C55 C 0.709(2) 0.426(2) 0.1777(17) 0.158(8) Uani 0.50 1 d PU A 1
H55A H 0.7655 0.3770 0.1656 0.237 Uiso 0.50 1 calc PR A 1
H55B H 0.6750 0.4573 0.1330 0.237 Uiso 0.50 1 calc PR A 1
H55C H 0.6549 0.4120 0.2106 0.237 Uiso 0.50 1 calc PR A 1
C56 C 0.906(2) 0.439(3) 0.245(2) 0.147(6) Uani 0.50 1 d PU A 1
H56A H 0.9197 0.4459 0.2946 0.220 Uiso 0.50 1 calc PR A 1
H56B H 0.9531 0.4601 0.2103 0.220 Uiso 0.50 1 calc PR A 1
H56C H 0.9208 0.3814 0.2404 0.220 Uiso 0.50 1 calc PR A 1
C57 C 0.779(2) 0.579(2) 0.1522(16) 0.165(6) Uani 0.50 1 d PDU A 1
C58 C 0.851(3) 0.554(2) 0.0825(15) 0.173(6) Uani 0.50 1 d PDU A 1
H58A H 0.8317 0.5128 0.0615 0.260 Uiso 0.50 1 calc PR A 1
H58B H 0.9267 0.5327 0.0957 0.260 Uiso 0.50 1 calc PR A 1
H58C H 0.8406 0.6022 0.0467 0.260 Uiso 0.50 1 calc PR A 1
C59 C 0.669(3) 0.623(2) 0.119(2) 0.178(8) Uani 0.50 1 d PDU A 1
H59A H 0.6278 0.6669 0.1482 0.267 Uiso 0.50 1 calc PR A 1
H59B H 0.6290 0.5847 0.1189 0.267 Uiso 0.50 1 calc PR A 1
H59C H 0.6785 0.6460 0.0690 0.267 Uiso 0.50 1 calc PR A 1
C60 C 0.842(3) 0.627(2) 0.184(2) 0.159(7) Uani 0.50 1 d PDU A 1
H60A H 0.8860 0.6455 0.1447 0.238 Uiso 0.50 1 calc PR A 1
H60B H 0.8892 0.5920 0.2217 0.238 Uiso 0.50 1 calc PR A 1
H60C H 0.7917 0.6743 0.2047 0.238 Uiso 0.50 1 calc PR A 1
C61 C 0.231(2) 0.472(2) 0.2192(18) 0.114(10) Uani 0.50 1 d PU A 1
H61A H 0.2709 0.4198 0.2451 0.171 Uiso 0.50 1 calc PR A 1
H61B H 0.1844 0.4638 0.1843 0.171 Uiso 0.50 1 calc PR A 1
H61C H 0.1871 0.5080 0.2543 0.171 Uiso 0.50 1 calc PR A 1
C62 C 0.429(3) 0.456(2) 0.0892(19) 0.134(14) Uani 0.50 1 d PU A 1
H62A H 0.4913 0.4755 0.0802 0.201 Uiso 0.50 1 calc PR A 1
H62B H 0.3903 0.4660 0.0442 0.201 Uiso 0.50 1 calc PR A 1
H62C H 0.4537 0.3982 0.1058 0.201 Uiso 0.50 1 calc PR A 1
C63 C 0.2612(19) 0.6261(15) 0.1159(13) 0.087(6) Uani 0.50 1 d PU A 1
C64 C 0.334(3) 0.668(2) 0.0804(18) 0.147(13) Uani 0.50 1 d PU A 1
H64A H 0.3378 0.6642 0.0279 0.221 Uiso 0.50 1 calc PR A 1
H64B H 0.4052 0.6429 0.1003 0.221 Uiso 0.50 1 calc PR A 1
H64C H 0.3062 0.7253 0.0893 0.221 Uiso 0.50 1 calc PR A 1
C65 C 0.195(3) 0.616(2) 0.0558(17) 0.155(11) Uani 0.50 1 d PU A 1
H65A H 0.2265 0.6296 0.0082 0.233 Uiso 0.50 1 calc PR A 1
H65B H 0.1212 0.6532 0.0604 0.233 Uiso 0.50 1 calc PR A 1
H65C H 0.1948 0.5603 0.0601 0.233 Uiso 0.50 1 calc PR A 1
C66 C 0.186(6) 0.692(4) 0.167(4) 0.24(3) Uani 0.50 1 d PU A 1
H66A H 0.1632 0.6642 0.2111 0.358 Uiso 0.50 1 calc PR A 1
H66B H 0.1227 0.7267 0.1403 0.358 Uiso 0.50 1 calc PR A 1
H66C H 0.2264 0.7258 0.1804 0.358 Uiso 0.50 1 calc PR A 1
Si3' Si 0.7500(10) 0.5453(9) 0.2051(6) 0.123(4) Uani 0.50 1 d PDU A 2
Si4' Si 0.3618(9) 0.5394(8) 0.1361(5) 0.121(4) Uani 0.50 1 d PU A 2
C55' C 0.651(3) 0.572(2) 0.128(2) 0.175(9) Uani 0.50 1 d PU A 2
H55D H 0.6105 0.5339 0.1332 0.263 Uiso 0.50 1 d PR A 2
H55E H 0.6923 0.5684 0.0821 0.263 Uiso 0.50 1 d PR A 2
H55F H 0.6009 0.6276 0.1298 0.263 Uiso 0.50 1 d PR A 2
C56' C 0.775(3) 0.656(3) 0.179(2) 0.164(7) Uani 0.50 1 d PU A 2
H56D H 0.7592 0.6750 0.1274 0.245 Uiso 0.50 1 d PR A 2
H56E H 0.8501 0.6492 0.1866 0.245 Uiso 0.50 1 d PR A 2
H56F H 0.7279 0.6952 0.2096 0.245 Uiso 0.50 1 d PR A 2
C57' C 0.857(2) 0.436(2) 0.1988(13) 0.169(6) Uani 0.50 1 d PDU A 2
C58' C 0.771(3) 0.3890(14) 0.2132(16) 0.165(7) Uani 0.50 1 d PDU A 2
H58D H 0.7966 0.3392 0.1890 0.248 Uiso 0.50 1 calc PR A 2
H58E H 0.7024 0.4238 0.1938 0.248 Uiso 0.50 1 calc PR A 2
H58F H 0.7626 0.3751 0.2657 0.248 Uiso 0.50 1 calc PR A 2
C59' C 0.893(2) 0.455(2) 0.1145(13) 0.184(7) Uani 0.50 1 d PDU A 2
H59D H 0.9355 0.4040 0.0952 0.276 Uiso 0.50 1 calc PR A 2
H59E H 0.9366 0.4910 0.1119 0.276 Uiso 0.50 1 calc PR A 2
H59F H 0.8292 0.4813 0.0857 0.276 Uiso 0.50 1 calc PR A 2
C60' C 0.956(2) 0.408(3) 0.252(2) 0.158(7) Uani 0.50 1 d PDU A 2
H60D H 0.9414 0.3725 0.2941 0.236 Uiso 0.50 1 calc PR A 2
H60E H 0.9659 0.4554 0.2685 0.236 Uiso 0.50 1 calc PR A 2
H60F H 1.0213 0.3776 0.2256 0.236 Uiso 0.50 1 calc PR A 2
C61' C 0.388(3) 0.615(2) 0.0557(17) 0.147(12) Uani 0.50 1 d PU A 2
H61D H 0.3355 0.6247 0.0181 0.220 Uiso 0.50 1 calc PR A 2
H61E H 0.4606 0.5925 0.0349 0.220 Uiso 0.50 1 calc PR A 2
H61F H 0.3807 0.6670 0.0740 0.220 Uiso 0.50 1 calc PR A 2
C62' C 0.400(2) 0.4307(17) 0.1160(17) 0.094(9) Uani 0.50 1 d PU A 2
H62D H 0.3753 0.3989 0.1564 0.141 Uiso 0.50 1 calc PR A 2
H62E H 0.4785 0.4082 0.1099 0.141 Uiso 0.50 1 calc PR A 2
H62F H 0.3669 0.4285 0.0710 0.141 Uiso 0.50 1 calc PR A 2
C63' C 0.217(3) 0.576(2) 0.1597(16) 0.158(11) Uani 0.50 1 d PDU A 2
C64' C 0.194(3) 0.519(2) 0.227(2) 0.151(15) Uani 0.50 1 d PDU A 2
H64D H 0.1634 0.5500 0.2677 0.227 Uiso 0.50 1 calc PR A 2
H64E H 0.2604 0.4756 0.2408 0.227 Uiso 0.50 1 calc PR A 2
H64F H 0.1420 0.4940 0.2129 0.227 Uiso 0.50 1 calc PR A 2
C66' C 0.180(3) 0.666(2) 0.181(2) 0.112(11) Uani 0.50 1 d PDU A 2
H66D H 0.1036 0.6914 0.1731 0.167 Uiso 0.50 1 calc PR A 2
H66E H 0.2209 0.6966 0.1514 0.167 Uiso 0.50 1 calc PR A 2
H66F H 0.1938 0.6643 0.2329 0.167 Uiso 0.50 1 calc PR A 2
C65' C 0.162(2) 0.561(2) 0.0927(17) 0.174(14) Uani 0.50 1 d PDU A 2
H65D H 0.1473 0.5095 0.1035 0.261 Uiso 0.50 1 d PR A 2
H65E H 0.2101 0.5586 0.0494 0.261 Uiso 0.50 1 d PR A 2
H65F H 0.0946 0.6053 0.0836 0.261 Uiso 0.50 1 d PR A 2


_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 C16 1.857(13) . ?
Br2 C49 1.894(9) . ?
Si1 C24 1.857(13) . ?
Si1 C22 1.860(9) . ?
Si1 C23 1.862(9) . ?
Si1 C3 1.885(9) . ?
Si2 C28 1.831(14) . ?
Si2 C30 1.858(14) . ?
Si2 C29 1.861(12) . ?
Si2 C6 1.871(11) . ?
N1 C2 1.263(10) . ?
N1 H1 0.8600 . ?
N2 C1 1.274(10) . ?
N2 C13 1.416(12) . ?
N3 C35 1.253(9) . ?
N3 H3 0.8600 . ?
N4 C34 1.272(10) . ?
N4 C46 1.420(10) . ?
O1 C9 1.357(10) . ?
O1 C19 1.419(10) . ?
O2 C10 1.365(9) . ?
O2 C20 1.460(10) . ?
O3 C11 1.365(9) . ?
O3 C21 1.435(10) . ?
O4 C42 1.365(10) . ?
O4 C52 1.409(11) . ?
O5 C43 1.370(9) . ?
O5 C53 1.435(9) . ?
O6 C44 1.346(10) . ?
O6 C54 1.408(12) . ?
C1 C7 1.472(11) . ?
C1 C2 1.511(12) . ?
C2 C3 1.514(10) . ?
C3 C4 1.356(11) . ?
C4 C5 1.406(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.182(11) . ?
C7 C12 1.378(10) . ?
C7 C8 1.384(11) . ?
C8 C9 1.412(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.410(11) . ?
C10 C11 1.387(11) . ?
C11 C12 1.387(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.339(14) . ?
C13 C18 1.382(15) . ?
C14 C15 1.378(15) . ?
C14 H14 0.9300 . ?
C15 C16 1.271(16) . ?
C15 H15 0.9300 . ?
C16 C17 1.356(18) . ?
C17 C18 1.474(17) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C26 1.457(17) . ?
C24 C27 1.526(15) . ?
C24 C25 1.63(2) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.490(15) . ?
C30 C32 1.530(14) . ?
C30 C33 1.562(18) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C40 1.486(11) . ?
C34 C35 1.517(11) . ?
C35 C36 1.508(11) . ?
C36 C37 1.318(11) . ?
C36 Si3 1.916(13) . ?
C36 Si3' 1.981(14) . ?
C37 C38 1.444(12) . ?
C37 H37 0.9300 . ?
C38 C39 1.219(12) . ?
C39 Si4 1.844(13) . ?
C39 Si4' 1.867(14) . ?
C40 C41 1.384(11) . ?
C40 C45 1.419(11) . ?
C41 C42 1.413(11) . ?
C41 H41 0.9300 . ?
C42 C43 1.383(12) . ?
C43 C44 1.381(12) . ?
C44 C45 1.374(11) . ?
C45 H45 0.9300 . ?
C46 C51 1.365(10) . ?
C46 C47 1.393(10) . ?
C47 C48 1.375(11) . ?
C47 H47 0.9300 . ?
C48 C49 1.345(11) . ?
C48 H48 0.9300 . ?
C49 C50 1.357(10) . ?
C50 C51 1.401(11) . ?
C50 H50 0.9300 . ?
C51 H51 0.9300 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 H53A 0.9600 . ?
C53 H53B 0.9600 . ?
C53 H53C 0.9600 . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
Si3 C56 1.72(3) . ?
Si3 C57 1.88(3) . ?
Si3 C55 1.92(2) . ?
Si4 C61 1.83(3) . ?
Si4 C63 1.92(3) . ?
Si4 C62 2.05(3) . ?
C55 H55A 0.9600 . ?
C55 H55B 0.9600 . ?
C55 H55C 0.9600 . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
C57 C59 1.507(19) . ?
C57 C60 1.530(19) . ?
C57 C58 1.532(18) . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C59 H59A 0.9600 . ?
C59 H59B 0.9600 . ?
C59 H59C 0.9600 . ?
C59 H55E 1.1700 . ?
C59 H55F 0.8625 . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 0.9600 . ?
C60 H56E 0.4331 . ?
C61 H61A 0.9600 . ?
C61 H61B 0.9600 . ?
C61 H61C 0.9600 . ?
C62 H62A 0.9600 . ?
C62 H62B 0.9600 . ?
C62 H62C 0.9600 . ?
C63 C64 1.43(3) . ?
C63 C65 1.49(3) . ?
C63 C66 1.58(6) . ?
C64 H64A 0.9600 . ?
C64 H64B 0.9600 . ?
C64 H64C 0.9600 . ?
C65 H65A 0.9600 . ?
C65 H65B 0.9600 . ?
C65 H65C 0.9600 . ?
C65 H65E 0.9701 . ?
C66 H66A 0.9600 . ?
C66 H66B 0.9600 . ?
C66 H66C 0.9600 . ?
Si3' C55' 1.87(4) . ?
Si3' C57' 1.95(4) . ?
Si3' C56' 2.02(4) . ?
Si4' C63' 1.80(3) . ?
Si4' C62' 1.85(3) . ?
Si4' C61' 1.92(3) . ?
C55' H55D 0.9600 . ?
C55' H55E 0.9600 . ?
C55' H55F 0.9600 . ?
C56' H56D 0.9600 . ?
C56' H56E 0.9600 . ?
C56' H56F 0.9600 . ?
C57' C58' 1.562(18) . ?
C57' C60' 1.569(19) . ?
C57' C59' 1.589(18) . ?
C58' H58D 0.9600 . ?
C58' H58E 0.9600 . ?
C58' H58F 0.9600 . ?
C59' H59D 0.9600 . ?
C59' H59E 0.9600 . ?
C59' H59F 0.9600 . ?
C60' H60D 0.9600 . ?
C60' H60E 0.9600 . ?
C60' H60F 0.9600 . ?
C61' H61D 0.9600 . ?
C61' H61E 0.9600 . ?
C61' H61F 0.9600 . ?
C62' H62D 0.9600 . ?
C62' H62E 0.9600 . ?
C62' H62F 0.9600 . ?
C63' C66' 1.543(19) . ?
C63' C65' 1.548(18) . ?
C63' C64' 1.549(19) . ?
C64' H64D 0.9600 . ?
C64' H64E 0.9600 . ?
C64' H64F 0.9600 . ?
C66' H66D 0.9600 . ?
C66' H66E 0.9600 . ?
C66' H66F 0.9600 . ?
C65' H65D 0.9600 . ?
C65' H65E 0.9600 . ?
C65' H65F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C24 Si1 C22 111.5(6) . . ?
C24 Si1 C23 110.5(6) . . ?
C22 Si1 C23 105.1(5) . . ?
C24 Si1 C3 110.1(5) . . ?
C22 Si1 C3 110.8(4) . . ?
C23 Si1 C3 108.7(5) . . ?
C28 Si2 C30 111.5(7) . . ?
C28 Si2 C29 112.2(7) . . ?
C30 Si2 C29 110.4(6) . . ?
C28 Si2 C6 106.5(6) . . ?
C30 Si2 C6 111.1(6) . . ?
C29 Si2 C6 104.8(5) . . ?
C2 N1 H1 180.0 . . ?
C1 N2 C13 119.1(9) . . ?
C35 N3 H3 180.0 . . ?
C34 N4 C46 122.2(7) . . ?
C9 O1 C19 117.6(7) . . ?
C10 O2 C20 118.6(6) . . ?
C11 O3 C21 116.7(6) . . ?
C42 O4 C52 117.4(8) . . ?
C43 O5 C53 115.0(6) . . ?
C44 O6 C54 117.4(8) . . ?
N2 C1 C7 118.4(9) . . ?
N2 C1 C2 124.2(8) . . ?
C7 C1 C2 117.4(9) . . ?
N1 C2 C1 121.2(7) . . ?
N1 C2 C3 119.3(8) . . ?
C1 C2 C3 119.4(8) . . ?
C4 C3 C2 115.1(8) . . ?
C4 C3 Si1 126.7(6) . . ?
C2 C3 Si1 118.1(6) . . ?
C3 C4 C5 127.8(9) . . ?
C3 C4 H4 116.1 . . ?
C5 C4 H4 116.1 . . ?
C6 C5 C4 172.3(11) . . ?
C5 C6 Si2 175.1(11) . . ?
C12 C7 C8 119.5(8) . . ?
C12 C7 C1 119.5(8) . . ?
C8 C7 C1 121.0(8) . . ?
C7 C8 C9 121.1(9) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
O1 C9 C10 115.8(8) . . ?
O1 C9 C8 126.0(9) . . ?
C10 C9 C8 118.2(9) . . ?
O2 C10 C11 118.6(8) . . ?
O2 C10 C9 121.4(9) . . ?
C11 C10 C9 119.9(8) . . ?
O3 C11 C12 124.6(8) . . ?
O3 C11 C10 115.0(7) . . ?
C12 C11 C10 120.4(8) . . ?
C7 C12 C11 120.8(8) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C18 119.3(11) . . ?
C14 C13 N2 122.9(11) . . ?
C18 C13 N2 117.5(11) . . ?
C13 C14 C15 121.5(13) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 123.8(14) . . ?
C16 C15 H15 118.1 . . ?
C14 C15 H15 118.1 . . ?
C15 C16 C17 117.8(13) . . ?
C15 C16 Br1 123.3(13) . . ?
C17 C16 Br1 118.9(12) . . ?
C16 C17 C18 122.2(13) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C13 C18 C17 115.2(13) . . ?
C13 C18 H18 122.4 . . ?
C17 C18 H18 122.4 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Si1 C22 H22A 109.5 . . ?
Si1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
Si1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Si1 C23 H23A 109.5 . . ?
Si1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
Si1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C26 C24 C27 110.0(14) . . ?
C26 C24 C25 111.2(13) . . ?
C27 C24 C25 102.0(12) . . ?
C26 C24 Si1 113.7(10) . . ?
C27 C24 Si1 113.2(8) . . ?
C25 C24 Si1 106.1(12) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 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 . . ?
Si2 C29 H29A 109.5 . . ?
Si2 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
Si2 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C32 111.6(11) . . ?
C31 C30 C33 107.9(13) . . ?
C32 C30 C33 108.6(12) . . ?
C31 C30 Si2 111.1(10) . . ?
C32 C30 Si2 109.1(10) . . ?
C33 C30 Si2 108.3(9) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N4 C34 C40 118.8(8) . . ?
N4 C34 C35 124.0(8) . . ?
C40 C34 C35 116.7(8) . . ?
N3 C35 C36 119.9(8) . . ?
N3 C35 C34 121.9(7) . . ?
C36 C35 C34 118.2(7) . . ?
C37 C36 C35 118.6(8) . . ?
C37 C36 Si3 125.6(7) . . ?
C35 C36 Si3 114.4(7) . . ?
C37 C36 Si3' 123.4(7) . . ?
C35 C36 Si3' 115.6(7) . . ?
Si3 C36 Si3' 26.4(4) . . ?
C36 C37 C38 128.8(9) . . ?
C36 C37 H37 115.6 . . ?
C38 C37 H37 115.6 . . ?
C39 C38 C37 175.8(11) . . ?
C38 C39 Si4 171.1(11) . . ?
C38 C39 Si4' 161.0(11) . . ?
Si4 C39 Si4' 25.8(3) . . ?
C41 C40 C45 119.9(8) . . ?
C41 C40 C34 120.7(8) . . ?
C45 C40 C34 119.4(8) . . ?
C40 C41 C42 118.2(8) . . ?
C40 C41 H41 120.9 . . ?
C42 C41 H41 120.9 . . ?
O4 C42 C43 116.0(9) . . ?
O4 C42 C41 122.8(9) . . ?
C43 C42 C41 121.2(8) . . ?
O5 C43 C44 120.2(9) . . ?
O5 C43 C42 119.4(9) . . ?
C44 C43 C42 120.1(8) . . ?
O6 C44 C45 125.7(10) . . ?
O6 C44 C43 114.4(9) . . ?
C45 C44 C43 119.9(9) . . ?
C44 C45 C40 120.5(8) . . ?
C44 C45 H45 119.7 . . ?
C40 C45 H45 119.7 . . ?
C51 C46 C47 117.8(8) . . ?
C51 C46 N4 123.2(7) . . ?
C47 C46 N4 118.9(8) . . ?
C48 C47 C46 120.4(8) . . ?
C48 C47 H47 119.8 . . ?
C46 C47 H47 119.8 . . ?
C49 C48 C47 120.1(8) . . ?
C49 C48 H48 119.9 . . ?
C47 C48 H48 119.9 . . ?
C48 C49 C50 122.0(8) . . ?
C48 C49 Br2 120.3(7) . . ?
C50 C49 Br2 117.7(7) . . ?
C49 C50 C51 117.7(8) . . ?
C49 C50 H50 121.1 . . ?
C51 C50 H50 121.1 . . ?
C46 C51 C50 121.9(7) . . ?
C46 C51 H51 119.0 . . ?
C50 C51 H51 119.0 . . ?
O4 C52 H52A 109.5 . . ?
O4 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
O4 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
O5 C53 H53A 109.5 . . ?
O5 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
O5 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
O6 C54 H54A 109.5 . . ?
O6 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
O6 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C56 Si3 C57 104.2(18) . . ?
C56 Si3 C36 117.3(13) . . ?
C57 Si3 C36 107.3(11) . . ?
C56 Si3 C55 110.5(18) . . ?
C57 Si3 C55 105.1(15) . . ?
C36 Si3 C55 111.4(11) . . ?
C61 Si4 C39 118.3(11) . . ?
C61 Si4 C63 115.0(13) . . ?
C39 Si4 C63 102.5(8) . . ?
C61 Si4 C62 117.4(15) . . ?
C39 Si4 C62 99.0(11) . . ?
C63 Si4 C62 101.9(13) . . ?
C59 C57 C60 121(3) . . ?
C59 C57 C58 102(3) . . ?
C60 C57 C58 99(3) . . ?
C59 C57 Si3 111(2) . . ?
C60 C57 Si3 107(2) . . ?
C58 C57 Si3 117(2) . . ?
C57 C59 H55E 84.5 . . ?
H59A C59 H55E 163.0 . . ?
H59B C59 H55E 55.2 . . ?
H59C C59 H55E 73.2 . . ?
C57 C59 H55F 138.0 . . ?
H59A C59 H55F 63.4 . . ?
H59B C59 H55F 48.3 . . ?
H59C C59 H55F 111.8 . . ?
H55E C59 H55F 99.8 . . ?
C57 C60 H56D 63.8 . . ?
H60A C60 H56D 77.2 . . ?
H60B C60 H56D 172.2 . . ?
H60C C60 H56D 70.9 . . ?
C57 C60 H56E 154.7 . . ?
H60A C60 H56E 63.4 . . ?
H60B C60 H56E 95.5 . . ?
H60C C60 H56E 56.4 . . ?
H56D C60 H56E 91.0 . . ?
C64 C63 C65 106(2) . . ?
C64 C63 C66 102(3) . . ?
C65 C63 C66 110(3) . . ?
C64 C63 Si4 117(2) . . ?
C65 C63 Si4 108.6(18) . . ?
C66 C63 Si4 113(3) . . ?
C63 C65 H65E 111.4 . . ?
H65A C65 H65E 94.7 . . ?
H65B C65 H65E 121.1 . . ?
H65C C65 H65E 15.7 . . ?
C63 C65 H65F 112.4 . . ?
H65A C65 H65F 136.9 . . ?
H65B C65 H65F 46.2 . . ?
H65C C65 H65F 65.2 . . ?
H65E C65 H65F 79.5 . . ?
C55' Si3' C57' 110.7(16) . . ?
C55' Si3' C36 112.7(13) . . ?
C57' Si3' C36 106.6(10) . . ?
C55' Si3' C56' 89.6(15) . . ?
C57' Si3' C56' 127.0(14) . . ?
C36 Si3' C56' 109.3(12) . . ?
C63' Si4' C62' 108.9(15) . . ?
C63' Si4' C39 105.0(10) . . ?
C62' Si4' C39 106.6(12) . . ?
C63' Si4' C61' 106.7(16) . . ?
C62' Si4' C61' 115.3(15) . . ?
C39 Si4' C61' 113.8(12) . . ?
Si3' C55' H55D 109.9 . . ?
Si3' C55' H55E 107.8 . . ?
H55D C55' H55E 109.5 . . ?
Si3' C55' H55F 110.7 . . ?
H55D C55' H55F 109.5 . . ?
H55E C55' H55F 109.5 . . ?
Si3' C56' H56D 109.8 . . ?
Si3' C56' H56E 109.3 . . ?
H56D C56' H56E 109.5 . . ?
Si3' C56' H56F 109.3 . . ?
H56D C56' H56F 109.5 . . ?
H56E C56' H56F 109.5 . . ?
C58' C57' C60' 117(3) . . ?
C58' C57' C59' 117(2) . . ?
C60' C57' C59' 112(3) . . ?
C58' C57' Si3' 94.9(17) . . ?
C60' C57' Si3' 118(2) . . ?
C59' C57' Si3' 94.9(17) . . ?
C57' C58' H58D 109.5 . . ?
C57' C58' H58E 109.5 . . ?
H58D C58' H58E 109.5 . . ?
C57' C58' H58F 109.5 . . ?
H58D C58' H58F 109.5 . . ?
H58E C58' H58F 109.5 . . ?
C57' C59' H59D 109.5 . . ?
C57' C59' H59E 109.5 . . ?
H59D C59' H59E 109.5 . . ?
C57' C59' H59F 109.5 . . ?
H59D C59' H59F 109.5 . . ?
H59E C59' H59F 109.5 . . ?
C57' C60' H60D 109.5 . . ?
C57' C60' H60E 109.5 . . ?
H60D C60' H60E 109.5 . . ?
C57' C60' H60F 109.5 . . ?
H60D C60' H60F 109.5 . . ?
H60E C60' H60F 109.5 . . ?
Si4' C61' H61D 109.5 . . ?
Si4' C61' H61E 109.5 . . ?
H61D C61' H61E 109.5 . . ?
Si4' C61' H61F 109.5 . . ?
H61D C61' H61F 109.5 . . ?
H61E C61' H61F 109.5 . . ?
Si4' C62' H62D 109.5 . . ?
Si4' C62' H62E 109.5 . . ?
H62D C62' H62E 109.5 . . ?
Si4' C62' H62F 109.5 . . ?
H62D C62' H62F 109.5 . . ?
H62E C62' H62F 109.5 . . ?
C66' C63' C65' 117(3) . . ?
C66' C63' C64' 109(3) . . ?
C65' C63' C64' 106(3) . . ?
C66' C63' Si4' 112(2) . . ?
C65' C63' Si4' 105(2) . . ?
C64' C63' Si4' 108(2) . . ?
C63' C64' H64D 109.5 . . ?
C63' C64' H64E 109.5 . . ?
H64D C64' H64E 109.5 . . ?
C63' C64' H64F 109.5 . . ?
H64D C64' H64F 109.5 . . ?
H64E C64' H64F 109.5 . . ?
C63' C66' H66D 109.5 . . ?
C63' C66' H66E 109.5 . . ?
H66D C66' H66E 109.5 . . ?
C63' C66' H66F 109.5 . . ?
H66D C66' H66F 109.5 . . ?
H66E C66' H66F 109.5 . . ?
C63' C65' H65D 109.5 . . ?
C63' C65' H65E 109.4 . . ?
H65D C65' H65E 109.5 . . ?
C63' C65' H65F 109.5 . . ?
H65D C65' H65F 109.5 . . ?
H65E C65' H65F 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
C13 N2 C1 C7 -173.0(8) . . . . ?
C13 N2 C1 C2 3.5(13) . . . . ?
N2 C1 C2 N1 -104.8(11) . . . . ?
C7 C1 C2 N1 71.7(11) . . . . ?
N2 C1 C2 C3 73.0(11) . . . . ?
C7 C1 C2 C3 -110.5(8) . . . . ?
N1 C2 C3 C4 -156.8(9) . . . . ?
C1 C2 C3 C4 25.4(12) . . . . ?
N1 C2 C3 Si1 20.5(11) . . . . ?
C1 C2 C3 Si1 -157.3(7) . . . . ?
C24 Si1 C3 C4 87.9(9) . . . . ?
C22 Si1 C3 C4 -148.3(9) . . . . ?
C23 Si1 C3 C4 -33.3(10) . . . . ?
C24 Si1 C3 C2 -89.0(8) . . . . ?
C22 Si1 C3 C2 34.8(8) . . . . ?
C23 Si1 C3 C2 149.8(7) . . . . ?
C2 C3 C4 C5 176.3(9) . . . . ?
Si1 C3 C4 C5 -0.7(16) . . . . ?
C3 C4 C5 C6 -168(9) . . . . ?
C4 C5 C6 Si2 -31(21) . . . . ?
C28 Si2 C6 C5 -51(13) . . . . ?
C30 Si2 C6 C5 -173(13) . . . . ?
C29 Si2 C6 C5 68(13) . . . . ?
N2 C1 C7 C12 8.2(11) . . . . ?
C2 C1 C7 C12 -168.6(7) . . . . ?
N2 C1 C7 C8 -172.9(8) . . . . ?
C2 C1 C7 C8 10.4(11) . . . . ?
C12 C7 C8 C9 2.1(12) . . . . ?
C1 C7 C8 C9 -176.8(7) . . . . ?
C19 O1 C9 C10 -175.2(7) . . . . ?
C19 O1 C9 C8 6.1(12) . . . . ?
C7 C8 C9 O1 177.8(7) . . . . ?
C7 C8 C9 C10 -0.8(12) . . . . ?
C20 O2 C10 C11 -122.3(8) . . . . ?
C20 O2 C10 C9 59.3(11) . . . . ?
O1 C9 C10 O2 -1.8(11) . . . . ?
C8 C9 C10 O2 177.0(7) . . . . ?
O1 C9 C10 C11 179.9(7) . . . . ?
C8 C9 C10 C11 -1.3(11) . . . . ?
C21 O3 C11 C12 -1.7(10) . . . . ?
C21 O3 C11 C10 178.2(7) . . . . ?
O2 C10 C11 O3 4.0(10) . . . . ?
C9 C10 C11 O3 -177.7(7) . . . . ?
O2 C10 C11 C12 -176.2(7) . . . . ?
C9 C10 C11 C12 2.1(11) . . . . ?
C8 C7 C12 C11 -1.3(11) . . . . ?
C1 C7 C12 C11 177.7(7) . . . . ?
O3 C11 C12 C7 179.0(7) . . . . ?
C10 C11 C12 C7 -0.8(11) . . . . ?
C1 N2 C13 C14 73.5(13) . . . . ?
C1 N2 C13 C18 -112.7(12) . . . . ?
C18 C13 C14 C15 0.6(19) . . . . ?
N2 C13 C14 C15 174.3(11) . . . . ?
C13 C14 C15 C16 4(2) . . . . ?
C14 C15 C16 C17 -4(3) . . . . ?
C14 C15 C16 Br1 177.4(11) . . . . ?
C15 C16 C17 C18 0(3) . . . . ?
Br1 C16 C17 C18 179.0(12) . . . . ?
C14 C13 C18 C17 -3.8(19) . . . . ?
N2 C13 C18 C17 -177.9(11) . . . . ?
C16 C17 C18 C13 4(2) . . . . ?
C22 Si1 C24 C26 171.9(12) . . . . ?
C23 Si1 C24 C26 55.4(14) . . . . ?
C3 Si1 C24 C26 -64.6(13) . . . . ?
C22 Si1 C24 C27 -61.6(12) . . . . ?
C23 Si1 C24 C27 -178.1(10) . . . . ?
C3 Si1 C24 C27 61.8(11) . . . . ?
C22 Si1 C24 C25 49.4(10) . . . . ?
C23 Si1 C24 C25 -67.1(11) . . . . ?
C3 Si1 C24 C25 172.9(9) . . . . ?
C28 Si2 C30 C31 -53.7(11) . . . . ?
C29 Si2 C30 C31 -179.2(9) . . . . ?
C6 Si2 C30 C31 64.9(11) . . . . ?
C28 Si2 C30 C32 69.8(11) . . . . ?
C29 Si2 C30 C32 -55.7(12) . . . . ?
C6 Si2 C30 C32 -171.5(10) . . . . ?
C28 Si2 C30 C33 -172.1(9) . . . . ?
C29 Si2 C30 C33 62.5(10) . . . . ?
C6 Si2 C30 C33 -53.4(10) . . . . ?
C46 N4 C34 C40 -174.5(6) . . . . ?
C46 N4 C34 C35 -2.7(12) . . . . ?
N4 C34 C35 N3 -104.4(10) . . . . ?
C40 C34 C35 N3 67.5(11) . . . . ?
N4 C34 C35 C36 77.2(11) . . . . ?
C40 C34 C35 C36 -110.9(8) . . . . ?
N3 C35 C36 C37 -166.9(9) . . . . ?
C34 C35 C36 C37 11.5(13) . . . . ?
N3 C35 C36 Si3 25.5(11) . . . . ?
C34 C35 C36 Si3 -156.0(7) . . . . ?
N3 C35 C36 Si3' -3.6(12) . . . . ?
C34 C35 C36 Si3' 174.8(8) . . . . ?
C35 C36 C37 C38 176.6(9) . . . . ?
Si3 C36 C37 C38 -17.4(16) . . . . ?
Si3' C36 C37 C38 14.7(16) . . . . ?
C36 C37 C38 C39 -132(15) . . . . ?
C37 C38 C39 Si4 -114(15) . . . . ?
C37 C38 C39 Si4' 114(15) . . . . ?
N4 C34 C40 C41 -179.5(7) . . . . ?
C35 C34 C40 C41 8.1(11) . . . . ?
N4 C34 C40 C45 -1.7(11) . . . . ?
C35 C34 C40 C45 -174.1(7) . . . . ?
C45 C40 C41 C42 3.4(11) . . . . ?
C34 C40 C41 C42 -178.9(6) . . . . ?
C52 O4 C42 C43 177.0(7) . . . . ?
C52 O4 C42 C41 -4.1(11) . . . . ?
C40 C41 C42 O4 177.5(7) . . . . ?
C40 C41 C42 C43 -3.6(11) . . . . ?
C53 O5 C43 C44 -91.5(9) . . . . ?
C53 O5 C43 C42 93.8(10) . . . . ?
O4 C42 C43 O5 -4.2(11) . . . . ?
C41 C42 C43 O5 176.8(6) . . . . ?
O4 C42 C43 C44 -179.0(7) . . . . ?
C41 C42 C43 C44 2.0(12) . . . . ?
C54 O6 C44 C45 -2.1(13) . . . . ?
C54 O6 C44 C43 177.7(8) . . . . ?
O5 C43 C44 O6 5.2(11) . . . . ?
C42 C43 C44 O6 179.9(7) . . . . ?
O5 C43 C44 C45 -175.0(7) . . . . ?
C42 C43 C44 C45 -0.2(12) . . . . ?
O6 C44 C45 C40 179.9(7) . . . . ?
C43 C44 C45 C40 0.1(11) . . . . ?
C41 C40 C45 C44 -1.7(11) . . . . ?
C34 C40 C45 C44 -179.5(7) . . . . ?
C34 N4 C46 C51 55.0(11) . . . . ?
C34 N4 C46 C47 -128.2(9) . . . . ?
C51 C46 C47 C48 -1.0(13) . . . . ?
N4 C46 C47 C48 -178.0(8) . . . . ?
C46 C47 C48 C49 -0.5(14) . . . . ?
C47 C48 C49 C50 2.7(14) . . . . ?
C47 C48 C49 Br2 -178.1(7) . . . . ?
C48 C49 C50 C51 -3.3(14) . . . . ?
Br2 C49 C50 C51 177.5(6) . . . . ?
C47 C46 C51 C50 0.4(13) . . . . ?
N4 C46 C51 C50 177.2(8) . . . . ?
C49 C50 C51 C46 1.7(13) . . . . ?
C37 C36 Si3 C56 -143.8(19) . . . . ?
C35 C36 Si3 C56 22.7(19) . . . . ?
Si3' C36 Si3 C56 122(2) . . . . ?
C37 C36 Si3 C57 99.4(14) . . . . ?
C35 C36 Si3 C57 -94.0(12) . . . . ?
Si3' C36 Si3 C57 4.9(13) . . . . ?
C37 C36 Si3 C55 -15.1(17) . . . . ?
C35 C36 Si3 C55 151.4(14) . . . . ?
Si3' C36 Si3 C55 -109.7(19) . . . . ?
C38 C39 Si4 C61 32(7) . . . . ?
Si4' C39 Si4 C61 178(2) . . . . ?
C38 C39 Si4 C63 160(6) . . . . ?
Si4' C39 Si4 C63 -53.9(14) . . . . ?
C38 C39 Si4 C62 -96(7) . . . . ?
Si4' C39 Si4 C62 50.5(16) . . . . ?
C56 Si3 C57 C59 170(3) . . . . ?
C36 Si3 C57 C59 -65(2) . . . . ?
C55 Si3 C57 C59 54(3) . . . . ?
C56 Si3 C57 C60 -56(3) . . . . ?
C36 Si3 C57 C60 69(2) . . . . ?
C55 Si3 C57 C60 -172(2) . . . . ?
C56 Si3 C57 C58 54(3) . . . . ?
C36 Si3 C57 C58 179(2) . . . . ?
C55 Si3 C57 C58 -62(3) . . . . ?
C61 Si4 C63 C64 176(2) . . . . ?
C39 Si4 C63 C64 46(2) . . . . ?
C62 Si4 C63 C64 -56(2) . . . . ?
C61 Si4 C63 C65 -64(2) . . . . ?
C39 Si4 C63 C65 166.2(18) . . . . ?
C62 Si4 C63 C65 64(2) . . . . ?
C61 Si4 C63 C66 58(3) . . . . ?
C39 Si4 C63 C66 -72(3) . . . . ?
C62 Si4 C63 C66 -174(3) . . . . ?
C37 C36 Si3' C55' 8.3(18) . . . . ?
C35 C36 Si3' C55' -154.1(15) . . . . ?
Si3 C36 Si3' C55' 112(2) . . . . ?
C37 C36 Si3' C57' -113.3(12) . . . . ?
C35 C36 Si3' C57' 84.3(11) . . . . ?
Si3 C36 Si3' C57' -9.4(11) . . . . ?
C37 C36 Si3' C56' 106.3(13) . . . . ?
C35 C36 Si3' C56' -56.1(14) . . . . ?
Si3 C36 Si3' C56' -149.8(19) . . . . ?
C38 C39 Si4' C63' -152(3) . . . . ?
Si4 C39 Si4' C63' 43.1(15) . . . . ?
C38 C39 Si4' C62' 92(3) . . . . ?
Si4 C39 Si4' C62' -72.3(16) . . . . ?
C38 C39 Si4' C61' -36(4) . . . . ?
Si4 C39 Si4' C61' 159(2) . . . . ?
C55' Si3' C57' C58' -64.1(19) . . . . ?
C36 Si3' C57' C58' 58.9(16) . . . . ?
C56' Si3' C57' C58' -170.1(18) . . . . ?
C55' Si3' C57' C60' 172(2) . . . . ?
C36 Si3' C57' C60' -65(2) . . . . ?
C56' Si3' C57' C60' 66(3) . . . . ?
C55' Si3' C57' C59' 54(2) . . . . ?
C36 Si3' C57' C59' 176.5(15) . . . . ?
C56' Si3' C57' C59' -52(2) . . . . ?
C62' Si4' C63' C66' 177(2) . . . . ?
C39 Si4' C63' C66' 63(2) . . . . ?
C61' Si4' C63' C66' -58(3) . . . . ?
C62' Si4' C63' C65' -55(3) . . . . ?
C39 Si4' C63' C65' -169(2) . . . . ?
C61' Si4' C63' C65' 70(3) . . . . ?
C62' Si4' C63' C64' 57(2) . . . . ?
C39 Si4' C63' C64' -57(2) . . . . ?
C61' Si4' C63' C64' -178(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O2 0.86 2.66 3.139(9) 116.5 .

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 988140'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_cd21461

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H35 Br N2 O2 S'
_chemical_formula_weight         603.60

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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                   13.9802(12)
_cell_length_b                   13.6497(11)
_cell_length_c                   16.6352(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.443(2)
_cell_angle_gamma                90
_cell_volume                     3074.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4387
_cell_measurement_theta_min      5.057
_cell_measurement_theta_max      48.833

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    1.436
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5743
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18278
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.956
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6044
_reflns_number_gt                4415
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0519P)²+0.9818P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6044
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.027
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.15290(3) 0.56948(3) 1.00562(2) 0.08763(17) Uani 1 1 d . . . . .
S1 S 0.57663(4) 0.36337(4) 0.55867(4) 0.03622(16) Uani 1 1 d . . . . .
N1 N 0.89461(13) 0.46031(14) 0.66750(12) 0.0357(4) Uani 1 1 d . . . . .
N2 N 0.65033(14) 0.44435(16) 0.53389(12) 0.0347(5) Uani 1 1 d . . . . .
O1 O 0.62080(13) 0.26953(12) 0.55893(11) 0.0477(4) Uani 1 1 d . . . . .
O2 O 0.48190(12) 0.38255(13) 0.50327(11) 0.0462(4) Uani 1 1 d . . . . .
C1 C 0.79647(16) 0.48624(16) 0.64673(13) 0.0323(5) Uani 1 1 d . . . . .
C2 C 0.75425(16) 0.44118(16) 0.57201(13) 0.0312(5) Uani 1 1 d . . . . .
C3 C 0.82733(17) 0.38883(17) 0.54351(14) 0.0347(5) Uani 1 1 d . . . . .
C4 C 0.91372(17) 0.40071(17) 0.60526(14) 0.0361(5) Uani 1 1 d . . . . .
C5 C 1.01059(18) 0.36389(18) 0.61323(15) 0.0411(6) Uani 1 1 d . . . . .
C6 C 1.09226(19) 0.3341(2) 0.62244(16) 0.0455(6) Uani 1 1 d . . . . .
C7 C 1.19389(19) 0.2969(2) 0.63361(18) 0.0525(7) Uani 1 1 d . . . . .
C8 C 1.2602(2) 0.3460(3) 0.7092(3) 0.0860(11) Uani 1 1 d . . . . .
H8A H 1.2596 0.4156 0.7007 0.129 Uiso 1 1 calc R U . . .
H8B H 1.3265 0.3219 0.7173 0.129 Uiso 1 1 calc R U . . .
H8C H 1.2365 0.3316 0.7573 0.129 Uiso 1 1 calc R U . . .
C9 C 1.2290(3) 0.3214(3) 0.5558(2) 0.0896(12) Uani 1 1 d . . . . .
H9A H 1.1852 0.2921 0.5082 0.134 Uiso 1 1 calc R U . . .
H9B H 1.2946 0.2964 0.5618 0.134 Uiso 1 1 calc R U . . .
H9C H 1.2293 0.3912 0.5486 0.134 Uiso 1 1 calc R U . . .
C10 C 1.1936(2) 0.1858(2) 0.6463(2) 0.0725(9) Uani 1 1 d . . . . .
H10A H 1.1663 0.1710 0.6924 0.109 Uiso 1 1 calc R U . . .
H10B H 1.2601 0.1615 0.6573 0.109 Uiso 1 1 calc R U . . .
H10C H 1.1543 0.1552 0.5970 0.109 Uiso 1 1 calc R U . . .
C11 C 0.75211(16) 0.55532(16) 0.69480(14) 0.0330(5) Uani 1 1 d . . . . .
C12 C 0.70034(17) 0.63533(17) 0.65454(15) 0.0404(6) Uani 1 1 d . . . . .
H12 H 0.6947 0.6444 0.5981 0.048 Uiso 1 1 calc R U . . .
C13 C 0.6571(2) 0.70173(19) 0.69726(18) 0.0505(7) Uani 1 1 d . . . . .
H13 H 0.6217 0.7545 0.6693 0.061 Uiso 1 1 calc R U . . .
C14 C 0.6661(2) 0.6902(2) 0.78080(18) 0.0546(7) Uani 1 1 d . . . . .
H14 H 0.6374 0.7353 0.8097 0.066 Uiso 1 1 calc R U . . .
C15 C 0.71803(19) 0.6110(2) 0.82166(16) 0.0481(6) Uani 1 1 d . . . . .
H15 H 0.7247 0.6032 0.8783 0.058 Uiso 1 1 calc R U . . .
C16 C 0.75984(18) 0.54383(18) 0.77929(15) 0.0393(6) Uani 1 1 d . . . . .
H16 H 0.7936 0.4902 0.8073 0.047 Uiso 1 1 calc R U . . .
C17 C 0.96411(15) 0.48578(17) 0.74364(14) 0.0354(5) Uani 1 1 d . . . . .
C18 C 0.98094(17) 0.58306(18) 0.76472(16) 0.0419(6) Uani 1 1 d . . . . .
H18 H 0.9543 0.6318 0.7266 0.050 Uiso 1 1 calc R U . . .
C19 C 1.03781(19) 0.6082(2) 0.84299(17) 0.0491(7) Uani 1 1 d . . . . .
H19 H 1.0479 0.6736 0.8585 0.059 Uiso 1 1 calc R U . . .
C20 C 1.07896(19) 0.5349(2) 0.89720(16) 0.0506(7) Uani 1 1 d . . . . .
C21 C 1.0667(2) 0.4378(2) 0.87576(18) 0.0536(7) Uani 1 1 d . . . . .
H21 H 1.0967 0.3894 0.9128 0.064 Uiso 1 1 calc R U . . .
C22 C 1.00885(18) 0.41320(19) 0.79797(16) 0.0443(6) Uani 1 1 d . . . . .
H22 H 1.0001 0.3477 0.7823 0.053 Uiso 1 1 calc R U . . .
C23 C 0.56517(17) 0.38779(18) 0.66006(15) 0.0376(5) Uani 1 1 d . . . . .
C24 C 0.50997(18) 0.4676(2) 0.67358(17) 0.0477(6) Uani 1 1 d . . . . .
H24 H 0.4800 0.5085 0.6298 0.057 Uiso 1 1 calc R U . . .
C25 C 0.5000(2) 0.4857(2) 0.75236(18) 0.0538(7) Uani 1 1 d . . . . .
H25 H 0.4627 0.5390 0.7615 0.065 Uiso 1 1 calc R U . . .
C26 C 0.5448(2) 0.4255(2) 0.81867(18) 0.0551(7) Uani 1 1 d . . . . .
C27 C 0.5991(2) 0.3473(2) 0.80365(18) 0.0596(8) Uani 1 1 d . . . . .
H27 H 0.6292 0.3065 0.8474 0.071 Uiso 1 1 calc R U . . .
C28 C 0.6104(2) 0.32739(19) 0.72487(17) 0.0488(6) Uani 1 1 d . . . . .
H28 H 0.6479 0.2741 0.7158 0.059 Uiso 1 1 calc R U . . .
C29 C 0.5337(3) 0.4478(3) 0.9049(2) 0.0875(12) Uani 1 1 d . . . . .
H29A H 0.5580 0.3935 0.9410 0.131 Uiso 1 1 calc R U . . .
H29B H 0.4653 0.4584 0.9029 0.131 Uiso 1 1 calc R U . . .
H29C H 0.5709 0.5056 0.9258 0.131 Uiso 1 1 calc R U . . .
C30 C 0.8199(2) 0.33259(19) 0.46281(15) 0.0437(6) Uani 1 1 d . . . . .
C31 C 0.8998(3) 0.3699(3) 0.42119(19) 0.0693(9) Uani 1 1 d . . . . .
H31A H 0.8920 0.4391 0.4117 0.104 Uiso 1 1 calc R U . . .
H31B H 0.8933 0.3368 0.3692 0.104 Uiso 1 1 calc R U . . .
H31C H 0.9640 0.3570 0.4568 0.104 Uiso 1 1 calc R U . . .
C32 C 0.8342(3) 0.2233(2) 0.48099(18) 0.0642(8) Uani 1 1 d . . . . .
H32A H 0.8967 0.2127 0.5199 0.096 Uiso 1 1 calc R U . . .
H32B H 0.8326 0.1888 0.4304 0.096 Uiso 1 1 calc R U . . .
H32C H 0.7821 0.1997 0.5041 0.096 Uiso 1 1 calc R U . . .
C33 C 0.7203(2) 0.3473(3) 0.39999(17) 0.0639(8) Uani 1 1 d . . . . .
H33A H 0.6689 0.3180 0.4209 0.096 Uiso 1 1 calc R U . . .
H33B H 0.7221 0.3169 0.3483 0.096 Uiso 1 1 calc R U . . .
H33C H 0.7076 0.4161 0.3914 0.096 Uiso 1 1 calc R U . . .
H2 H 0.6213(18) 0.4973(19) 0.5264(15) 0.035(7) Uiso 1 1 d . . . . .


_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 C20 1.901(2) . ?
S1 O1 1.4216(17) . ?
S1 O2 1.4363(16) . ?
S1 N2 1.633(2) . ?
S1 C23 1.765(2) . ?
N1 C1 1.375(3) . ?
N1 C4 1.394(3) . ?
N1 C17 1.434(3) . ?
N2 C2 1.434(3) . ?
N2 H2 0.82(3) . ?
C1 C2 1.380(3) . ?
C1 C11 1.470(3) . ?
C2 C3 1.422(3) . ?
C3 C4 1.386(3) . ?
C3 C30 1.527(3) . ?
C4 C5 1.419(3) . ?
C5 C6 1.185(3) . ?
C6 C7 1.476(3) . ?
C7 C8 1.520(5) . ?
C7 C9 1.532(4) . ?
C7 C10 1.532(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.387(3) . ?
C11 C16 1.391(3) . ?
C12 C13 1.381(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.378(3) . ?
C17 C22 1.381(3) . ?
C18 C19 1.389(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.373(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.371(4) . ?
C21 C22 1.386(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C28 1.379(3) . ?
C23 C24 1.385(4) . ?
C24 C25 1.374(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.392(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.369(4) . ?
C26 C29 1.512(4) . ?
C27 C28 1.385(4) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C32 1.525(4) . ?
C30 C33 1.531(4) . ?
C30 C31 1.541(4) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.76(10) . . ?
O1 S1 N2 108.04(11) . . ?
O2 S1 N2 104.69(11) . . ?
O1 S1 C23 108.07(11) . . ?
O2 S1 C23 106.85(11) . . ?
N2 S1 C23 109.08(11) . . ?
C1 N1 C4 109.13(18) . . ?
C1 N1 C17 124.99(19) . . ?
C4 N1 C17 125.77(18) . . ?
C2 N2 S1 120.11(16) . . ?
C2 N2 H2 120.0(17) . . ?
S1 N2 H2 108.3(17) . . ?
N1 C1 C2 106.70(19) . . ?
N1 C1 C11 123.94(19) . . ?
C2 C1 C11 129.20(19) . . ?
C1 C2 C3 110.05(19) . . ?
C1 C2 N2 122.9(2) . . ?
C3 C2 N2 126.9(2) . . ?
C4 C3 C2 105.06(19) . . ?
C4 C3 C30 124.5(2) . . ?
C2 C3 C30 130.4(2) . . ?
C3 C4 N1 109.01(19) . . ?
C3 C4 C5 131.5(2) . . ?
N1 C4 C5 119.5(2) . . ?
C6 C5 C4 177.9(3) . . ?
C5 C6 C7 179.8(3) . . ?
C6 C7 C8 108.8(3) . . ?
C6 C7 C9 108.7(2) . . ?
C8 C7 C9 110.2(3) . . ?
C6 C7 C10 108.8(2) . . ?
C8 C7 C10 110.2(3) . . ?
C9 C7 C10 110.2(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 118.4(2) . . ?
C12 C11 C1 118.9(2) . . ?
C16 C11 C1 122.7(2) . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.4(2) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.5(2) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C18 C17 C22 120.2(2) . . ?
C18 C17 N1 119.6(2) . . ?
C22 C17 N1 120.0(2) . . ?
C17 C18 C19 119.8(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 119.0(3) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C21 C20 C19 121.9(2) . . ?
C21 C20 Br1 119.3(2) . . ?
C19 C20 Br1 118.8(2) . . ?
C20 C21 C22 118.9(2) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C17 C22 C21 120.0(2) . . ?
C17 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C28 C23 C24 120.6(2) . . ?
C28 C23 S1 120.1(2) . . ?
C24 C23 S1 119.38(18) . . ?
C25 C24 C23 119.3(2) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 121.2(3) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C27 C26 C25 118.4(3) . . ?
C27 C26 C29 121.5(3) . . ?
C25 C26 C29 120.1(3) . . ?
C26 C27 C28 121.7(3) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 H27 119.2 . . ?
C23 C28 C27 119.0(3) . . ?
C23 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C32 C30 C3 109.9(2) . . ?
C32 C30 C33 108.4(2) . . ?
C3 C30 C33 112.7(2) . . ?
C32 C30 C31 109.8(2) . . ?
C3 C30 C31 109.3(2) . . ?
C33 C30 C31 106.7(2) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
O1 S1 N2 C2 -45.6(2) . . . . ?
O2 S1 N2 C2 -174.30(17) . . . . ?
C23 S1 N2 C2 71.6(2) . . . . ?
C4 N1 C1 C2 1.0(3) . . . . ?
C17 N1 C1 C2 -175.4(2) . . . . ?
C4 N1 C1 C11 -174.8(2) . . . . ?
C17 N1 C1 C11 8.9(3) . . . . ?
N1 C1 C2 C3 -2.1(3) . . . . ?
C11 C1 C2 C3 173.3(2) . . . . ?
N1 C1 C2 N2 174.5(2) . . . . ?
C11 C1 C2 N2 -10.0(4) . . . . ?
S1 N2 C2 C1 -86.6(3) . . . . ?
S1 N2 C2 C3 89.5(3) . . . . ?
C1 C2 C3 C4 2.4(3) . . . . ?
N2 C2 C3 C4 -174.1(2) . . . . ?
C1 C2 C3 C30 -175.9(2) . . . . ?
N2 C2 C3 C30 7.6(4) . . . . ?
C2 C3 C4 N1 -1.8(3) . . . . ?
C30 C3 C4 N1 176.7(2) . . . . ?
C2 C3 C4 C5 178.3(3) . . . . ?
C30 C3 C4 C5 -3.2(4) . . . . ?
C1 N1 C4 C3 0.5(3) . . . . ?
C17 N1 C4 C3 176.9(2) . . . . ?
C1 N1 C4 C5 -179.5(2) . . . . ?
C17 N1 C4 C5 -3.2(3) . . . . ?
N1 C1 C11 C12 125.6(2) . . . . ?
C2 C1 C11 C12 -49.2(3) . . . . ?
N1 C1 C11 C16 -54.5(3) . . . . ?
C2 C1 C11 C16 130.8(3) . . . . ?
C16 C11 C12 C13 -0.3(4) . . . . ?
C1 C11 C12 C13 179.7(2) . . . . ?
C11 C12 C13 C14 1.0(4) . . . . ?
C12 C13 C14 C15 -0.6(4) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C14 C15 C16 C11 1.2(4) . . . . ?
C12 C11 C16 C15 -0.8(4) . . . . ?
C1 C11 C16 C15 179.2(2) . . . . ?
C1 N1 C17 C18 -58.7(3) . . . . ?
C4 N1 C17 C18 125.6(3) . . . . ?
C1 N1 C17 C22 117.1(3) . . . . ?
C4 N1 C17 C22 -58.7(3) . . . . ?
C22 C17 C18 C19 -4.3(4) . . . . ?
N1 C17 C18 C19 171.4(2) . . . . ?
C17 C18 C19 C20 2.0(4) . . . . ?
C18 C19 C20 C21 1.0(4) . . . . ?
C18 C19 C20 Br1 -177.8(2) . . . . ?
C19 C20 C21 C22 -1.8(5) . . . . ?
Br1 C20 C21 C22 177.0(2) . . . . ?
C18 C17 C22 C21 3.4(4) . . . . ?
N1 C17 C22 C21 -172.2(2) . . . . ?
C20 C21 C22 C17 -0.4(4) . . . . ?
O1 S1 C23 C28 9.9(2) . . . . ?
O2 S1 C23 C28 140.0(2) . . . . ?
N2 S1 C23 C28 -107.3(2) . . . . ?
O1 S1 C23 C24 -169.7(2) . . . . ?
O2 S1 C23 C24 -39.5(2) . . . . ?
N2 S1 C23 C24 73.1(2) . . . . ?
C28 C23 C24 C25 -0.5(4) . . . . ?
S1 C23 C24 C25 179.1(2) . . . . ?
C23 C24 C25 C26 0.3(4) . . . . ?
C24 C25 C26 C27 -0.1(4) . . . . ?
C24 C25 C26 C29 179.2(3) . . . . ?
C25 C26 C27 C28 0.2(4) . . . . ?
C29 C26 C27 C28 -179.2(3) . . . . ?
C24 C23 C28 C27 0.5(4) . . . . ?
S1 C23 C28 C27 -179.1(2) . . . . ?
C26 C27 C28 C23 -0.3(4) . . . . ?
C4 C3 C30 C32 69.4(3) . . . . ?
C2 C3 C30 C32 -112.5(3) . . . . ?
C4 C3 C30 C33 -169.6(2) . . . . ?
C2 C3 C30 C33 8.5(4) . . . . ?
C4 C3 C30 C31 -51.1(3) . . . . ?
C2 C3 C30 C31 126.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.82(3) 2.16(3) 2.969(3) 168(2) 3_666

_refine_diff_density_max         0.760
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 988141'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cd212474

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 N2 O2'
_chemical_formula_weight         420.49

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'

_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                   9.4812(19)
_cell_length_b                   10.0987(19)
_cell_length_c                   13.636(3)
_cell_angle_alpha                74.849(5)
_cell_angle_beta                 80.124(5)
_cell_angle_gamma                67.332(4)
_cell_volume                     1159.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1055
_cell_measurement_theta_min      4.671
_cell_measurement_theta_max      51.004

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.112
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.34212
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7000
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4549
_reflns_number_gt                2407
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0685P)²+0.0000P] 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         4549
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1225
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_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
N1 N 0.29026(19) 0.09565(18) 0.38106(12) 0.0529(5) Uani 1 1 d . . .
N2 N 0.4359(2) -0.03860(19) 0.18209(13) 0.0572(5) Uani 1 1 d . . .
O1 O 0.4648(2) 0.56900(17) 0.16180(14) 0.0936(6) Uani 1 1 d . . .
O2 O -0.1424(2) 0.2631(2) 0.02834(13) 0.0907(6) Uani 1 1 d . . .
C1 C 0.3486(2) -0.0345(2) 0.36385(14) 0.0467(5) Uani 1 1 d . . .
C2 C 0.4689(2) -0.0745(2) 0.27603(15) 0.0487(5) Uani 1 1 d . . .
C3 C 0.6334(2) -0.1526(2) 0.29800(15) 0.0473(5) Uani 1 1 d . . .
C4 C 0.7467(2) -0.1835(2) 0.21865(17) 0.0606(6) Uani 1 1 d . . .
H4 H 0.7191 -0.1564 0.1520 0.073 Uiso 1 1 calc R . .
C5 C 0.8991(3) -0.2537(3) 0.2377(2) 0.0737(7) Uani 1 1 d . . .
H5 H 0.9731 -0.2739 0.1838 0.088 Uiso 1 1 calc R . .
C6 C 0.9434(3) -0.2948(3) 0.3367(2) 0.0693(7) Uani 1 1 d . . .
H6 H 1.0463 -0.3424 0.3493 0.083 Uiso 1 1 calc R . .
C7 C 0.8325(3) -0.2640(2) 0.41566(18) 0.0644(6) Uani 1 1 d . . .
H7 H 0.8607 -0.2904 0.4821 0.077 Uiso 1 1 calc R . .
C8 C 0.6792(2) -0.1938(2) 0.39671(16) 0.0566(6) Uani 1 1 d . . .
H8 H 0.6056 -0.1737 0.4508 0.068 Uiso 1 1 calc R . .
C9 C 0.2953(2) -0.1516(2) 0.43201(15) 0.0485(5) Uani 1 1 d . . .
C10 C 0.3484(3) -0.2935(2) 0.41355(17) 0.0591(6) Uani 1 1 d . . .
H10 H 0.4186 -0.3166 0.3583 0.071 Uiso 1 1 calc R . .
C11 C 0.2964(3) -0.3998(2) 0.47755(19) 0.0693(7) Uani 1 1 d . . .
H11 H 0.3330 -0.4943 0.4655 0.083 Uiso 1 1 calc R . .
C12 C 0.1907(3) -0.3662(3) 0.55895(19) 0.0725(7) Uani 1 1 d . . .
H12 H 0.1559 -0.4379 0.6013 0.087 Uiso 1 1 calc R . .
C13 C 0.1365(3) -0.2265(3) 0.57753(18) 0.0692(7) Uani 1 1 d . . .
H13 H 0.0645 -0.2039 0.6320 0.083 Uiso 1 1 calc R . .
C14 C 0.1893(2) -0.1188(2) 0.51490(16) 0.0575(6) Uani 1 1 d . . .
H14 H 0.1538 -0.0253 0.5284 0.069 Uiso 1 1 calc R . .
C15 C 0.3426(2) 0.2111(2) 0.32198(15) 0.0502(5) Uani 1 1 d . . .
C16 C 0.2416(3) 0.3335(2) 0.26216(18) 0.0660(7) Uani 1 1 d . . .
H16 H 0.1428 0.3381 0.2583 0.079 Uiso 1 1 calc R . .
C17 C 0.2877(3) 0.4480(2) 0.20869(19) 0.0735(7) Uani 1 1 d . . .
H17 H 0.2207 0.5276 0.1670 0.088 Uiso 1 1 calc R . .
C18 C 0.4319(3) 0.4463(2) 0.21606(17) 0.0646(6) Uani 1 1 d . . .
C19 C 0.5328(3) 0.3263(2) 0.27676(17) 0.0629(6) Uani 1 1 d . . .
H19 H 0.6302 0.3239 0.2825 0.075 Uiso 1 1 calc R . .
C20 C 0.4869(3) 0.2093(2) 0.32921(16) 0.0579(6) Uani 1 1 d . . .
H20 H 0.5547 0.1287 0.3698 0.069 Uiso 1 1 calc R . .
C21 C 0.6156(4) 0.5656(3) 0.1580(2) 0.1023(10) Uani 1 1 d . . .
H21A H 0.6433 0.5478 0.2260 0.154 Uiso 1 1 calc R . .
H21B H 0.6213 0.6582 0.1200 0.154 Uiso 1 1 calc R . .
H21C H 0.6849 0.4885 0.1254 0.154 Uiso 1 1 calc R . .
C22 C 0.2825(3) 0.0357(2) 0.15257(15) 0.0564(6) Uani 1 1 d . . .
C23 C 0.1641(3) -0.0172(3) 0.18665(17) 0.0686(7) Uani 1 1 d . . .
H23 H 0.1803 -0.1028 0.2370 0.082 Uiso 1 1 calc R . .
C24 C 0.0213(3) 0.0549(3) 0.14727(18) 0.0722(7) Uani 1 1 d . . .
H24 H -0.0560 0.0163 0.1703 0.087 Uiso 1 1 calc R . .
C25 C -0.0059(3) 0.1841(3) 0.07376(17) 0.0670(6) Uani 1 1 d . . .
C26 C 0.1108(3) 0.2406(3) 0.04053(19) 0.0782(7) Uani 1 1 d . . .
H26 H 0.0931 0.3289 -0.0072 0.094 Uiso 1 1 calc R . .
C27 C 0.2530(3) 0.1656(3) 0.07835(17) 0.0735(7) Uani 1 1 d . . .
H27 H 0.3311 0.2027 0.0537 0.088 Uiso 1 1 calc R . .
C28 C -0.2538(3) 0.1944(3) 0.0454(2) 0.0964(9) Uani 1 1 d . . .
H28A H -0.2073 0.1000 0.0276 0.145 Uiso 1 1 calc R . .
H28B H -0.3375 0.2548 0.0040 0.145 Uiso 1 1 calc R . .
H28C H -0.2912 0.1822 0.1159 0.145 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
N1 C1 1.282(2) . ?
N1 C15 1.440(2) . ?
N2 C2 1.295(2) . ?
N2 C22 1.429(3) . ?
O1 C18 1.385(2) . ?
O1 C21 1.409(3) . ?
O2 C25 1.385(3) . ?
O2 C28 1.430(3) . ?
C1 C9 1.497(3) . ?
C1 C2 1.526(3) . ?
C2 C3 1.494(3) . ?
C3 C8 1.394(3) . ?
C3 C4 1.393(3) . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.386(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C14 1.395(3) . ?
C9 C10 1.400(3) . ?
C10 C11 1.388(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.396(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.381(3) . ?
C15 C16 1.393(3) . ?
C16 C17 1.378(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(3) . ?
C19 C20 1.395(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.383(3) . ?
C22 C27 1.395(3) . ?
C23 C24 1.392(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.385(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.391(3) . ?
C26 C27 1.379(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C15 121.42(16) . . ?
C2 N2 C22 122.72(18) . . ?
C18 O1 C21 118.3(2) . . ?
C25 O2 C28 117.4(2) . . ?
N1 C1 C9 118.69(17) . . ?
N1 C1 C2 122.65(16) . . ?
C9 C1 C2 118.66(17) . . ?
N2 C2 C3 118.07(18) . . ?
N2 C2 C1 122.94(19) . . ?
C3 C2 C1 118.93(17) . . ?
C8 C3 C4 117.9(2) . . ?
C8 C3 C2 121.86(18) . . ?
C4 C3 C2 120.21(19) . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 119.0(2) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C3 121.2(2) . . ?
C7 C8 H8 119.4 . . ?
C3 C8 H8 119.4 . . ?
C14 C9 C10 119.06(18) . . ?
C14 C9 C1 119.67(18) . . ?
C10 C9 C1 121.26(18) . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 120.0(2) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C20 C15 C16 118.78(19) . . ?
C20 C15 N1 121.65(19) . . ?
C16 C15 N1 119.36(19) . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 121.0(2) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 O1 116.4(2) . . ?
C17 C18 C19 119.4(2) . . ?
O1 C18 C19 124.2(2) . . ?
C18 C19 C20 119.4(2) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C15 C20 C19 121.2(2) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 117.6(2) . . ?
C23 C22 N2 124.82(19) . . ?
C27 C22 N2 117.4(2) . . ?
C22 C23 C24 121.4(2) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C25 C24 C23 120.1(2) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
O2 C25 C24 124.8(2) . . ?
O2 C25 C26 116.0(2) . . ?
C24 C25 C26 119.2(2) . . ?
C27 C26 C25 120.0(2) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C22 121.7(2) . . ?
C26 C27 H27 119.2 . . ?
C22 C27 H27 119.2 . . ?
O2 C28 H28A 109.5 . . ?
O2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
C15 N1 C1 C9 176.46(18) . . . . ?
C15 N1 C1 C2 -4.2(3) . . . . ?
C22 N2 C2 C3 179.69(17) . . . . ?
C22 N2 C2 C1 -3.1(3) . . . . ?
N1 C1 C2 N2 -75.6(3) . . . . ?
C9 C1 C2 N2 103.7(2) . . . . ?
N1 C1 C2 C3 101.5(2) . . . . ?
C9 C1 C2 C3 -79.1(2) . . . . ?
N2 C2 C3 C8 179.27(18) . . . . ?
C1 C2 C3 C8 2.0(3) . . . . ?
N2 C2 C3 C4 0.7(3) . . . . ?
C1 C2 C3 C4 -176.54(18) . . . . ?
C8 C3 C4 C5 0.5(3) . . . . ?
C2 C3 C4 C5 179.12(19) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C3 -0.1(3) . . . . ?
C4 C3 C8 C7 -0.4(3) . . . . ?
C2 C3 C8 C7 -178.91(18) . . . . ?
N1 C1 C9 C14 -2.8(3) . . . . ?
C2 C1 C9 C14 177.80(19) . . . . ?
N1 C1 C9 C10 176.36(19) . . . . ?
C2 C1 C9 C10 -3.0(3) . . . . ?
C14 C9 C10 C11 -0.4(3) . . . . ?
C1 C9 C10 C11 -179.6(2) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C10 C9 C14 C13 -0.6(3) . . . . ?
C1 C9 C14 C13 178.6(2) . . . . ?
C12 C13 C14 C9 1.1(3) . . . . ?
C1 N1 C15 C20 -68.8(3) . . . . ?
C1 N1 C15 C16 116.5(2) . . . . ?
C20 C15 C16 C17 2.2(3) . . . . ?
N1 C15 C16 C17 177.12(19) . . . . ?
C15 C16 C17 C18 -2.4(4) . . . . ?
C16 C17 C18 O1 -177.9(2) . . . . ?
C16 C17 C18 C19 1.2(4) . . . . ?
C21 O1 C18 C17 -173.2(2) . . . . ?
C21 O1 C18 C19 7.7(3) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
O1 C18 C19 C20 179.1(2) . . . . ?
C16 C15 C20 C19 -0.9(3) . . . . ?
N1 C15 C20 C19 -175.73(19) . . . . ?
C18 C19 C20 C15 -0.2(3) . . . . ?
C2 N2 C22 C23 -58.9(3) . . . . ?
C2 N2 C22 C27 126.0(2) . . . . ?
C27 C22 C23 C24 1.1(3) . . . . ?
N2 C22 C23 C24 -174.0(2) . . . . ?
C22 C23 C24 C25 -1.3(4) . . . . ?
C28 O2 C25 C24 -11.2(3) . . . . ?
C28 O2 C25 C26 168.0(2) . . . . ?
C23 C24 C25 O2 178.8(2) . . . . ?
C23 C24 C25 C26 -0.3(4) . . . . ?
O2 C25 C26 C27 -177.1(2) . . . . ?
C24 C25 C26 C27 2.1(4) . . . . ?
C25 C26 C27 C22 -2.3(4) . . . . ?
C23 C22 C27 C26 0.7(4) . . . . ?
N2 C22 C27 C26 176.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.032
_database_code_depnum_ccdc_archive 'CCDC 988142'
