# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177

_publ_contact_author             
;
Prof. Dr. Bernhard W\"unsch
Institut f\"ur Pharmazeutische und Medizinische Chemie
der Universit\"at M\"unster
Hittorfstr. 58 - 62
D-48149 M\"unster
Bundesrepublik Deutschland
;
_publ_contact_author_phone       '49 251 83-33311'
_publ_contact_author_fax         '49 251 83-32144'
_publ_contact_author_email       wuensch@uni-muenster.de
_publ_requested_coeditor_name    ?

_publ_contact_letter             
;
Dear Teresa,

after some time of silence again a structure from Muenster
(the last onces went to RSC journals ...).

We are fine, but a little bit tired due the ongoing winter
(without any salt for the roads, so it is often very slippery).

I hope your injuries are totally gone and you are now fit enough
to cycle to work again. Please say greetings to your family!

Best wishes and regards to you

Roland
;

#==========================================================================

# 3. TITLE AND AUTHOR LIST

_publ_section_title              
;
Bicyclic \s Receptor Ligands by Dieckmann Analogous Cyclization
of Piperazinebutyrate
;

loop_
_publ_author_name
_publ_author_address
'S.Kumar Sunnam'
; Institut f \"ur Pharamazeutische und Medizinische Chemie
der Universit\"at M\"unster
Hittorfstrasse 58-62
D-48149 M\"unster
Germany
;
D.Schepmann
; Institut f \"ur Pharamazeutische und Medizinische Chemie
der Universit\"at M\"unster
Hittorfstrasse 58-62
D-48149 M\"unster
Germany
;
B.Wunsch
; Institut f \"ur Pharamazeutische und Medizinische Chemie
der Universit\"at M\"unster
Hittorfstrasse 58-62
D-48149 M\"unster
Germany
;
B.Wibbeling
; Organisch-Chemisches Institut
der Universit\"at M\"unster
Corrensstrasse 40
D-48149 M\"unster
Germany
;
#==========================================================================

data_fro5270
_database_code_depnum_ccdc_archive 'CCDC 766603'
#TrackingRef 'wuensch5270.cam'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H30 N2 O4 Si'
_chemical_formula_weight         390.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.9326(1)
_cell_length_b                   10.1183(1)
_cell_length_c                   11.8959(1)
_cell_angle_alpha                82.320(1)
_cell_angle_beta                 80.314(1)
_cell_angle_gamma                86.226(1)
_cell_volume                     1049.316(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    3863
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.20

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    1.210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6432
_exptl_absorpt_correction_T_max  0.9646
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12315
_diffrn_reflns_av_R_equivalents  0.057
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.41
_diffrn_reflns_theta_max         67.47
_reflns_number_total             3630
_reflns_number_gt                3025
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to Zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0603P)^2^+0.6129P] where P=(Fo^2^+2Fc^2^)/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         3630
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1172
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
C1 C 0.1175(2) 0.6293(2) 0.85256(17) 0.0326(4) Uani 1 1 d . . .
H1 H 0.1354 0.5404 0.8954 0.039 Uiso 1 1 calc R . .
C2 C 0.1897(2) 0.6188(2) 0.72564(18) 0.0365(5) Uani 1 1 d . . .
C3 C 0.2168(3) 0.7524(2) 0.65075(19) 0.0429(5) Uani 1 1 d . . .
H3A H 0.2652 0.7347 0.5737 0.051 Uiso 1 1 calc R . .
H3B H 0.2889 0.8001 0.6823 0.051 Uiso 1 1 calc R . .
C4 C 0.0761(3) 0.8444(2) 0.63910(19) 0.0437(5) Uani 1 1 d . . .
H4A H 0.0892 0.8920 0.5610 0.052 Uiso 1 1 calc R . .
H4B H -0.0118 0.7887 0.6478 0.052 Uiso 1 1 calc R . .
C5 C 0.0395(3) 0.9470(2) 0.7234(2) 0.0433(5) Uani 1 1 d . . .
H5A H -0.0476 1.0037 0.7029 0.052 Uiso 1 1 calc R . .
H5B H 0.1263 1.0043 0.7133 0.052 Uiso 1 1 calc R . .
C6 C 0.0027(2) 0.8915(2) 0.85154(19) 0.0381(5) Uani 1 1 d . . .
H6 H -0.0481 0.9656 0.8922 0.046 Uiso 1 1 calc R . .
N7 N -0.10358(19) 0.78307(17) 0.87437(15) 0.0348(4) Uani 1 1 d . . .
C8 C -0.0541(2) 0.6557(2) 0.87118(16) 0.0331(5) Uani 1 1 d . . .
O1 O -0.13867(17) 0.56184(15) 0.88744(14) 0.0435(4) Uani 1 1 d . . .
N9 N 0.19458(19) 0.72318(18) 0.90387(15) 0.0361(4) Uani 1 1 d . . .
C10 C 0.1469(2) 0.8520(2) 0.90108(18) 0.0375(5) Uani 1 1 d . . .
O2 O 0.21366(19) 0.93609(16) 0.93598(15) 0.0512(4) Uani 1 1 d . . .
C11 C -0.2655(2) 0.8173(2) 0.9103(2) 0.0424(5) Uani 1 1 d . . .
H11A H -0.2772 0.8610 0.9802 0.051 Uiso 1 1 calc R . .
H11B H -0.3213 0.7349 0.9291 0.051 Uiso 1 1 calc R . .
C12 C -0.3342(2) 0.9078(2) 0.8198(2) 0.0404(5) Uani 1 1 d . . .
C13 C -0.3930(3) 1.0328(2) 0.8414(2) 0.0475(6) Uani 1 1 d . . .
H13 H -0.3921 1.0605 0.9136 0.057 Uiso 1 1 calc R . .
C14 C -0.4533(3) 1.1181(3) 0.7575(3) 0.0642(7) Uani 1 1 d . . .
H14 H -0.4949 1.2027 0.7732 0.077 Uiso 1 1 calc R . .
C15 C -0.4518(4) 1.0785(4) 0.6517(3) 0.0770(9) Uani 1 1 d . . .
H15 H -0.4906 1.1369 0.5941 0.092 Uiso 1 1 calc R . .
C16 C -0.3940(4) 0.9541(4) 0.6292(3) 0.0767(9) Uani 1 1 d . . .
H16 H -0.3931 0.9275 0.5563 0.092 Uiso 1 1 calc R . .
C17 C -0.3372(3) 0.8681(3) 0.7135(2) 0.0598(7) Uani 1 1 d . . .
H17 H -0.3003 0.7820 0.6985 0.072 Uiso 1 1 calc R . .
C18 C 0.3310(3) 0.6772(3) 0.9524(2) 0.0481(6) Uani 1 1 d . . .
H18A H 0.4203 0.6977 0.8954 0.072 Uiso 1 1 calc R . .
H18B H 0.3293 0.5815 0.9750 0.072 Uiso 1 1 calc R . .
H18C H 0.3343 0.7217 1.0192 0.072 Uiso 1 1 calc R . .
O3 O 0.32836(17) 0.54551(16) 0.73835(14) 0.0458(4) Uani 1 1 d . . .
C19 C 0.4400(3) 0.5397(3) 0.6383(3) 0.0664(8) Uani 1 1 d . . .
H19A H 0.3912 0.5247 0.5744 0.100 Uiso 1 1 calc R . .
H19B H 0.5136 0.4672 0.6524 0.100 Uiso 1 1 calc R . .
H19C H 0.4912 0.6234 0.6198 0.100 Uiso 1 1 calc R . .
O4 O 0.09653(17) 0.54714(14) 0.67345(12) 0.0375(4) Uani 1 1 d . . .
Si Si 0.06003(7) 0.38613(6) 0.68883(5) 0.03908(19) Uani 1 1 d . . .
C20 C 0.0917(3) 0.2952(2) 0.8286(2) 0.0544(7) Uani 1 1 d . . .
H20A H 0.1931 0.3106 0.8418 0.082 Uiso 1 1 calc R . .
H20B H 0.0817 0.2004 0.8281 0.082 Uiso 1 1 calc R . .
H20C H 0.0171 0.3267 0.8894 0.082 Uiso 1 1 calc R . .
C21 C 0.1832(4) 0.3078(3) 0.5706(2) 0.0624(8) Uani 1 1 d . . .
H21A H 0.1703 0.3580 0.4973 0.094 Uiso 1 1 calc R . .
H21B H 0.1546 0.2166 0.5724 0.094 Uiso 1 1 calc R . .
H21C H 0.2887 0.3080 0.5807 0.094 Uiso 1 1 calc R . .
C22 C -0.1400(3) 0.3801(3) 0.6693(3) 0.0631(7) Uani 1 1 d . . .
H22A H -0.2043 0.4330 0.7222 0.095 Uiso 1 1 calc R . .
H22B H -0.1705 0.2883 0.6843 0.095 Uiso 1 1 calc R . .
H22C H -0.1503 0.4157 0.5910 0.095 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0346(11) 0.0321(11) 0.0314(10) -0.0072(8) -0.0026(8) -0.0041(8)
C2 0.0366(11) 0.0377(11) 0.0349(11) -0.0079(9) -0.0021(9) -0.0027(9)
C3 0.0507(13) 0.0412(12) 0.0343(11) -0.0065(9) 0.0053(10) -0.0117(10)
C4 0.0602(15) 0.0355(12) 0.0341(11) 0.0013(9) -0.0067(10) -0.0073(10)
C5 0.0518(13) 0.0329(11) 0.0451(13) -0.0008(10) -0.0085(11) -0.0075(10)
C6 0.0410(12) 0.0314(11) 0.0434(12) -0.0118(9) -0.0049(9) -0.0035(9)
N7 0.0319(9) 0.0351(9) 0.0379(9) -0.0078(7) -0.0034(7) -0.0031(7)
C8 0.0388(11) 0.0345(11) 0.0265(10) -0.0071(8) -0.0027(8) -0.0059(9)
O1 0.0408(8) 0.0376(8) 0.0520(9) -0.0088(7) -0.0004(7) -0.0120(7)
N9 0.0355(9) 0.0402(10) 0.0348(9) -0.0094(7) -0.0065(7) -0.0052(8)
C10 0.0406(12) 0.0390(12) 0.0340(11) -0.0121(9) -0.0010(9) -0.0083(9)
O2 0.0516(10) 0.0476(9) 0.0612(11) -0.0216(8) -0.0129(8) -0.0119(8)
C11 0.0354(12) 0.0457(13) 0.0455(13) -0.0088(10) -0.0027(10) -0.0002(10)
C12 0.0325(11) 0.0466(13) 0.0446(12) -0.0110(10) -0.0081(9) -0.0044(9)
C13 0.0452(13) 0.0501(14) 0.0490(14) -0.0113(11) -0.0097(11) -0.0005(11)
C14 0.0623(17) 0.0562(16) 0.075(2) -0.0023(14) -0.0211(15) 0.0071(13)
C15 0.0666(19) 0.099(3) 0.066(2) 0.0071(18) -0.0312(16) 0.0079(18)
C16 0.073(2) 0.111(3) 0.0571(18) -0.0265(17) -0.0339(15) 0.0132(19)
C17 0.0554(15) 0.0698(18) 0.0634(17) -0.0275(14) -0.0244(13) 0.0075(13)
C18 0.0414(13) 0.0556(15) 0.0510(14) -0.0060(11) -0.0158(11) -0.0076(11)
O3 0.0377(8) 0.0531(10) 0.0443(9) -0.0117(7) 0.0017(7) 0.0050(7)
C19 0.0476(15) 0.083(2) 0.0626(18) -0.0177(15) 0.0123(13) 0.0055(14)
O4 0.0508(9) 0.0324(8) 0.0305(7) -0.0071(6) -0.0063(6) -0.0050(6)
Si 0.0541(4) 0.0315(3) 0.0326(3) -0.0068(2) -0.0072(3) -0.0027(3)
C20 0.0845(19) 0.0373(13) 0.0413(13) -0.0042(10) -0.0117(13) -0.0006(12)
C21 0.098(2) 0.0417(14) 0.0449(14) -0.0133(11) 0.0008(14) 0.0015(14)
C22 0.0682(18) 0.0527(16) 0.0736(19) -0.0057(13) -0.0229(15) -0.0168(13)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N9 1.460(3) . ?
C1 C8 1.522(3) . ?
C1 C2 1.554(3) . ?
C1 H1 0.9900 . ?
C2 O4 1.406(3) . ?
C2 O3 1.421(3) . ?
C2 C3 1.526(3) . ?
C3 C4 1.528(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 C5 1.521(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C6 1.541(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 N7 1.466(3) . ?
C6 C10 1.513(3) . ?
C6 H6 0.9900 . ?
N7 C8 1.338(3) . ?
N7 C11 1.470(3) . ?
C8 O1 1.227(2) . ?
N9 C10 1.342(3) . ?
N9 C18 1.458(3) . ?
C10 O2 1.223(3) . ?
C11 C12 1.503(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 C13 1.376(3) . ?
C12 C17 1.382(3) . ?
C13 C14 1.386(4) . ?
C13 H13 0.9400 . ?
C14 C15 1.369(4) . ?
C14 H14 0.9400 . ?
C15 C16 1.371(5) . ?
C15 H15 0.9400 . ?
C16 C17 1.378(4) . ?
C16 H16 0.9400 . ?
C17 H17 0.9400 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
O3 C19 1.424(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
O4 Si 1.6625(15) . ?
Si C20 1.846(2) . ?
Si C22 1.846(3) . ?
Si C21 1.865(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?

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
N9 C1 C8 111.99(16) . . ?
N9 C1 C2 112.03(16) . . ?
C8 C1 C2 114.32(16) . . ?
N9 C1 H1 105.9 . . ?
C8 C1 H1 105.9 . . ?
C2 C1 H1 105.9 . . ?
O4 C2 O3 110.79(17) . . ?
O4 C2 C3 107.36(17) . . ?
O3 C2 C3 111.75(18) . . ?
O4 C2 C1 110.10(16) . . ?
O3 C2 C1 102.01(16) . . ?
C3 C2 C1 114.82(17) . . ?
C2 C3 C4 116.15(19) . . ?
C2 C3 H3A 108.2 . . ?
C4 C3 H3A 108.2 . . ?
C2 C3 H3B 108.2 . . ?
C4 C3 H3B 108.2 . . ?
H3A C3 H3B 107.4 . . ?
C5 C4 C3 116.42(19) . . ?
C5 C4 H4A 108.2 . . ?
C3 C4 H4A 108.2 . . ?
C5 C4 H4B 108.2 . . ?
C3 C4 H4B 108.2 . . ?
H4A C4 H4B 107.3 . . ?
C4 C5 C6 116.30(18) . . ?
C4 C5 H5A 108.2 . . ?
C6 C5 H5A 108.2 . . ?
C4 C5 H5B 108.2 . . ?
C6 C5 H5B 108.2 . . ?
H5A C5 H5B 107.4 . . ?
N7 C6 C10 111.92(17) . . ?
N7 C6 C5 113.45(17) . . ?
C10 C6 C5 110.93(18) . . ?
N7 C6 H6 106.7 . . ?
C10 C6 H6 106.7 . . ?
C5 C6 H6 106.7 . . ?
C8 N7 C6 121.26(17) . . ?
C8 N7 C11 120.65(18) . . ?
C6 N7 C11 117.89(17) . . ?
O1 C8 N7 123.67(19) . . ?
O1 C8 C1 119.84(18) . . ?
N7 C8 C1 116.40(17) . . ?
C10 N9 C18 119.82(18) . . ?
C10 N9 C1 121.06(17) . . ?
C18 N9 C1 119.01(18) . . ?
O2 C10 N9 123.4(2) . . ?
O2 C10 C6 119.9(2) . . ?
N9 C10 C6 116.70(18) . . ?
N7 C11 C12 113.00(18) . . ?
N7 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N7 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C17 119.0(2) . . ?
C13 C12 C11 120.2(2) . . ?
C17 C12 C11 120.8(2) . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
N9 C18 H18A 109.5 . . ?
N9 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N9 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 O3 C19 117.65(19) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 O4 Si 132.17(13) . . ?
O4 Si C20 113.71(10) . . ?
O4 Si C22 105.88(11) . . ?
C20 Si C22 111.07(14) . . ?
O4 Si C21 108.28(10) . . ?
C20 Si C21 109.35(13) . . ?
C22 Si C21 108.36(14) . . ?
Si C20 H20A 109.5 . . ?
Si C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Si C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Si C21 H21A 109.5 . . ?
Si C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
Si C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Si C22 H22A 109.5 . . ?
Si C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
Si C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
N9 C1 C2 O4 -169.34(16) . . . . ?
C8 C1 C2 O4 -40.6(2) . . . . ?
N9 C1 C2 O3 73.0(2) . . . . ?
C8 C1 C2 O3 -158.23(16) . . . . ?
N9 C1 C2 C3 -48.1(2) . . . . ?
C8 C1 C2 C3 80.7(2) . . . . ?
O4 C2 C3 C4 63.0(2) . . . . ?
O3 C2 C3 C4 -175.32(17) . . . . ?
C1 C2 C3 C4 -59.8(3) . . . . ?
C2 C3 C4 C5 93.4(2) . . . . ?
C3 C4 C5 C6 -62.5(3) . . . . ?
C4 C5 C6 N7 -45.9(3) . . . . ?
C4 C5 C6 C10 81.0(2) . . . . ?
C10 C6 N7 C8 -37.8(3) . . . . ?
C5 C6 N7 C8 88.7(2) . . . . ?
C10 C6 N7 C11 137.26(19) . . . . ?
C5 C6 N7 C11 -96.3(2) . . . . ?
C6 N7 C8 O1 -178.52(19) . . . . ?
C11 N7 C8 O1 6.6(3) . . . . ?
C6 N7 C8 C1 4.9(3) . . . . ?
C11 N7 C8 C1 -170.01(18) . . . . ?
N9 C1 C8 O1 -144.20(19) . . . . ?
C2 C1 C8 O1 87.0(2) . . . . ?
N9 C1 C8 N7 32.5(2) . . . . ?
C2 C1 C8 N7 -96.3(2) . . . . ?
C8 C1 N9 C10 -37.9(3) . . . . ?
C2 C1 N9 C10 92.1(2) . . . . ?
C8 C1 N9 C18 145.86(19) . . . . ?
C2 C1 N9 C18 -84.2(2) . . . . ?
C18 N9 C10 O2 1.2(3) . . . . ?
C1 N9 C10 O2 -175.0(2) . . . . ?
C18 N9 C10 C6 -178.83(19) . . . . ?
C1 N9 C10 C6 5.0(3) . . . . ?
N7 C6 C10 O2 -147.7(2) . . . . ?
C5 C6 C10 O2 84.5(2) . . . . ?
N7 C6 C10 N9 32.4(3) . . . . ?
C5 C6 C10 N9 -95.4(2) . . . . ?
C8 N7 C11 C12 -121.3(2) . . . . ?
C6 N7 C11 C12 63.7(2) . . . . ?
N7 C11 C12 C13 -118.2(2) . . . . ?
N7 C11 C12 C17 60.7(3) . . . . ?
C17 C12 C13 C14 -0.4(4) . . . . ?
C11 C12 C13 C14 178.5(2) . . . . ?
C12 C13 C14 C15 -1.2(4) . . . . ?
C13 C14 C15 C16 1.4(5) . . . . ?
C14 C15 C16 C17 0.1(5) . . . . ?
C15 C16 C17 C12 -1.8(5) . . . . ?
C13 C12 C17 C16 2.0(4) . . . . ?
C11 C12 C17 C16 -176.9(3) . . . . ?
O4 C2 O3 C19 75.3(2) . . . . ?
C3 C2 O3 C19 -44.3(3) . . . . ?
C1 C2 O3 C19 -167.5(2) . . . . ?
O3 C2 O4 Si 39.8(2) . . . . ?
C3 C2 O4 Si 162.10(15) . . . . ?
C1 C2 O4 Si -72.3(2) . . . . ?
C2 O4 Si C20 23.8(2) . . . . ?
C2 O4 Si C22 146.03(19) . . . . ?
C2 O4 Si C21 -97.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        67.47
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.044
#====================================================================== _eof