# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2004


data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Christopher A. Reed'
'Christopher Richardson'

_publ_contact_author_name        'Dr Christopher A. Reed'
_publ_contact_author_address     
;
Department of Chemistry
University of California
Riverside
California
CA 92521
UNITED STATES OF AMERICA
;

_publ_contact_author_email       CHRIS.REED@UCR.EDU

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
Exploration of the pentacyano-cyclo-pentadienide
ion, C5(CN)5-, as a weakly coordinating anion and potential superacid
conjugate base. Silylation and protonation
;

data_cr131m
_database_code_depnum_ccdc_archive 'CCDC 227124'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H15 N5'
_chemical_formula_weight         433.46

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   12.802(2)
_cell_length_b                   8.1247(15)
_cell_length_c                   22.816(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.491(5)
_cell_angle_gamma                90.00
_cell_volume                     2307.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       'Frag. of prism'
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   SADABS
_exptl_absorpt_correction_T_min  0.9657
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-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            13042
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         26.37
_reflns_number_total             4700
_reflns_number_gt                3173
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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^)+(0.0358P)^2^+0.6014P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4700
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.59243(12) 0.21274(19) 0.20320(7) 0.0392(4) Uani 1 1 d . . .
C2 C 0.70263(12) 0.21910(19) 0.23804(7) 0.0384(4) Uani 1 1 d . . .
C3 C 0.78808(13) 0.1744(2) 0.21195(8) 0.0442(4) Uani 1 1 d . . .
H3 H 0.7737 0.1416 0.1713 0.052(5) Uiso 1 1 calc R . .
C4 C 0.89249(14) 0.1783(2) 0.24556(9) 0.0521(5) Uani 1 1 d . . .
H4 H 0.9489 0.1472 0.2279 0.059(5) Uiso 1 1 calc R . .
C5 C 0.91457(14) 0.2277(2) 0.30524(9) 0.0537(5) Uani 1 1 d . . .
H5 H 0.9860 0.2299 0.3280 0.063(6) Uiso 1 1 calc R . .
C6 C 0.83230(14) 0.2738(2) 0.33152(8) 0.0509(5) Uani 1 1 d . . .
H6 H 0.8480 0.3087 0.3719 0.056(5) Uiso 1 1 calc R . .
C7 C 0.72730(13) 0.2688(2) 0.29882(7) 0.0429(4) Uani 1 1 d . . .
H7 H 0.6717 0.2988 0.3172 0.048(5) Uiso 1 1 calc R . .
C8 C 0.50494(12) 0.1826(2) 0.23174(7) 0.0393(4) Uani 1 1 d . . .
C9 C 0.51802(14) 0.0814(2) 0.28326(8) 0.0471(4) Uani 1 1 d . . .
H9 H 0.5859 0.0370 0.3010 0.045(5) Uiso 1 1 calc R . .
C10 C 0.43194(15) 0.0477(2) 0.30750(8) 0.0554(5) Uani 1 1 d . . .
H10 H 0.4408 -0.0218 0.3412 0.065(6) Uiso 1 1 calc R . .
C11 C 0.33198(15) 0.1151(2) 0.28273(9) 0.0552(5) Uani 1 1 d . . .
H11 H 0.2737 0.0918 0.2999 0.070(6) Uiso 1 1 calc R . .
C12 C 0.31763(14) 0.2164(2) 0.23278(8) 0.0514(5) Uani 1 1 d . . .
H12 H 0.2498 0.2625 0.2163 0.065(6) Uiso 1 1 calc R . .
C13 C 0.40231(13) 0.2499(2) 0.20721(8) 0.0445(4) Uani 1 1 d . . .
H13 H 0.3919 0.3181 0.1731 0.043(5) Uiso 1 1 calc R . .
C14 C 0.56819(12) 0.2337(2) 0.13847(7) 0.0414(4) Uani 1 1 d . . .
C15 C 0.48372(13) 0.1437(2) 0.10159(8) 0.0500(5) Uani 1 1 d . . .
H15 H 0.4425 0.0716 0.1193 0.052(5) Uiso 1 1 calc R . .
C16 C 0.46121(15) 0.1606(3) 0.03993(9) 0.0610(5) Uani 1 1 d . . .
H16 H 0.4056 0.0988 0.0156 0.075(6) Uiso 1 1 calc R . .
C17 C 0.52048(16) 0.2685(3) 0.01393(9) 0.0664(6) Uani 1 1 d . . .
H17 H 0.5044 0.2802 -0.0282 0.075(6) Uiso 1 1 calc R . .
C18 C 0.60294(15) 0.3593(3) 0.04897(8) 0.0590(5) Uani 1 1 d . . .
H18 H 0.6421 0.4333 0.0307 0.064(6) Uiso 1 1 calc R . .
C19 C 0.62795(14) 0.3416(2) 0.11069(8) 0.0467(4) Uani 1 1 d . . .
H19 H 0.6852 0.4018 0.1344 0.045(5) Uiso 1 1 calc R . .
C1' C 0.56290(12) 0.7824(2) 0.49819(7) 0.0396(4) Uani 1 1 d . . .
C2' C 0.62138(12) 0.7055(2) 0.55106(7) 0.0402(4) Uani 1 1 d . . .
C3' C 0.54730(13) 0.6254(2) 0.57830(7) 0.0402(4) Uani 1 1 d . . .
C4' C 0.44355(12) 0.6535(2) 0.54226(7) 0.0395(4) Uani 1 1 d . . .
C5' C 0.45297(12) 0.7507(2) 0.49306(7) 0.0398(4) Uani 1 1 d . . .
C6' C 0.60653(13) 0.8733(2) 0.45588(8) 0.0454(4) Uani 1 1 d . . .
C7' C 0.73487(14) 0.7074(2) 0.57392(8) 0.0471(4) Uani 1 1 d . . .
C8' C 0.56990(13) 0.5293(2) 0.63190(8) 0.0470(4) Uani 1 1 d . . .
C9' C 0.34726(14) 0.5904(2) 0.55473(7) 0.0442(4) Uani 1 1 d . . .
C10' C 0.36623(14) 0.8111(2) 0.44694(7) 0.0445(4) Uani 1 1 d . . .
N1' N 0.64018(12) 0.9458(2) 0.42136(7) 0.0619(4) Uani 1 1 d . . .
N2' N 0.82575(13) 0.7084(2) 0.59312(8) 0.0670(5) Uani 1 1 d . . .
N3' N 0.58432(13) 0.4505(2) 0.67467(8) 0.0657(5) Uani 1 1 d . . .
N4' N 0.27145(12) 0.5365(2) 0.56569(7) 0.0596(4) Uani 1 1 d . . .
N5' N 0.29637(13) 0.8615(2) 0.41051(7) 0.0625(5) Uani 1 1 d . . .

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 0.0397(9) 0.0309(8) 0.0445(9) -0.0031(7) 0.0050(7) 0.0007(7)
C2 0.0359(8) 0.0327(8) 0.0444(9) -0.0015(7) 0.0051(7) 0.0000(7)
C3 0.0419(9) 0.0416(10) 0.0480(10) -0.0039(8) 0.0084(8) 0.0005(7)
C4 0.0377(9) 0.0519(11) 0.0665(12) -0.0015(9) 0.0121(9) 0.0025(8)
C5 0.0360(10) 0.0521(11) 0.0654(12) 0.0002(9) -0.0035(9) -0.0022(8)
C6 0.0469(10) 0.0535(11) 0.0456(10) -0.0034(8) -0.0031(8) -0.0015(9)
C7 0.0418(9) 0.0419(10) 0.0429(9) -0.0021(7) 0.0055(7) -0.0002(8)
C8 0.0367(8) 0.0389(9) 0.0401(9) -0.0026(7) 0.0043(7) -0.0015(7)
C9 0.0399(10) 0.0470(10) 0.0508(10) 0.0037(8) 0.0035(8) 0.0005(8)
C10 0.0522(11) 0.0613(12) 0.0522(11) 0.0104(9) 0.0111(9) -0.0058(9)
C11 0.0444(10) 0.0611(12) 0.0622(12) -0.0033(10) 0.0165(9) -0.0090(9)
C12 0.0373(10) 0.0544(11) 0.0606(11) -0.0037(9) 0.0077(8) 0.0006(8)
C13 0.0386(9) 0.0464(10) 0.0450(10) -0.0006(8) 0.0023(7) -0.0002(8)
C14 0.0363(8) 0.0440(10) 0.0416(9) -0.0040(7) 0.0042(7) 0.0024(7)
C15 0.0393(9) 0.0575(12) 0.0500(10) -0.0103(9) 0.0037(8) -0.0018(8)
C16 0.0470(11) 0.0805(15) 0.0492(11) -0.0177(10) -0.0015(9) 0.0038(10)
C17 0.0559(12) 0.1001(18) 0.0395(11) -0.0014(11) 0.0040(9) 0.0166(12)
C18 0.0511(11) 0.0762(14) 0.0503(11) 0.0124(10) 0.0131(9) 0.0090(10)
C19 0.0411(9) 0.0498(10) 0.0472(10) 0.0009(8) 0.0061(8) 0.0018(8)
C1' 0.0378(9) 0.0420(9) 0.0386(9) -0.0058(7) 0.0077(7) 0.0007(7)
C2' 0.0354(8) 0.0436(10) 0.0413(9) -0.0060(7) 0.0083(7) 0.0034(7)
C3' 0.0401(9) 0.0420(9) 0.0378(9) -0.0058(7) 0.0081(7) 0.0043(7)
C4' 0.0376(9) 0.0424(9) 0.0391(9) -0.0085(7) 0.0099(7) 0.0009(7)
C5' 0.0376(8) 0.0442(9) 0.0362(8) -0.0072(7) 0.0056(7) 0.0029(7)
C6' 0.0378(9) 0.0544(11) 0.0416(10) -0.0013(8) 0.0045(8) 0.0048(8)
C7' 0.0424(10) 0.0523(11) 0.0458(10) 0.0004(8) 0.0085(8) 0.0034(8)
C8' 0.0388(9) 0.0537(11) 0.0484(10) -0.0007(9) 0.0097(8) 0.0050(8)
C9' 0.0416(10) 0.0520(11) 0.0383(9) -0.0057(8) 0.0078(8) 0.0027(8)
C10' 0.0403(9) 0.0531(11) 0.0397(9) -0.0049(8) 0.0086(8) -0.0018(8)
N1' 0.0508(9) 0.0795(12) 0.0568(10) 0.0145(9) 0.0151(8) 0.0059(9)
N2' 0.0421(9) 0.0861(13) 0.0677(11) 0.0034(9) 0.0027(8) 0.0057(9)
N3' 0.0553(10) 0.0803(13) 0.0614(10) 0.0197(10) 0.0135(8) 0.0070(9)
N4' 0.0467(9) 0.0767(12) 0.0563(10) 0.0001(8) 0.0138(7) -0.0032(8)
N5' 0.0497(9) 0.0796(12) 0.0522(10) 0.0024(9) -0.0005(8) 0.0023(9)

_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 C8 1.442(2) . ?
C1 C14 1.447(2) . ?
C1 C2 1.450(2) . ?
C2 C7 1.408(2) . ?
C2 C3 1.410(2) . ?
C3 C4 1.378(2) . ?
C4 C5 1.384(3) . ?
C5 C6 1.380(3) . ?
C6 C7 1.377(2) . ?
C8 C9 1.412(2) . ?
C8 C13 1.413(2) . ?
C9 C10 1.371(2) . ?
C10 C11 1.385(3) . ?
C11 C12 1.383(3) . ?
C12 C13 1.373(2) . ?
C14 C19 1.408(2) . ?
C14 C15 1.410(2) . ?
C15 C16 1.375(3) . ?
C16 C17 1.381(3) . ?
C17 C18 1.380(3) . ?
C18 C19 1.377(2) . ?
C1' C5' 1.408(2) . ?
C1' C2' 1.409(2) . ?
C1' C6' 1.429(2) . ?
C2' C3' 1.409(2) . ?
C2' C7' 1.425(2) . ?
C3' C4' 1.408(2) . ?
C3' C8' 1.423(2) . ?
C4' C5' 1.401(2) . ?
C4' C9' 1.424(2) . ?
C5' C10' 1.427(2) . ?
C6' N1' 1.145(2) . ?
C7' N2' 1.144(2) . ?
C8' N3' 1.145(2) . ?
C9' N4' 1.145(2) . ?
C10' N5' 1.145(2) . ?

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
C8 C1 C14 118.48(14) . . ?
C8 C1 C2 121.18(14) . . ?
C14 C1 C2 120.34(14) . . ?
C7 C2 C3 118.17(14) . . ?
C7 C2 C1 121.09(14) . . ?
C3 C2 C1 120.74(14) . . ?
C4 C3 C2 120.46(16) . . ?
C3 C4 C5 120.22(16) . . ?
C6 C5 C4 120.32(16) . . ?
C7 C6 C5 120.27(17) . . ?
C6 C7 C2 120.55(16) . . ?
C9 C8 C13 118.27(15) . . ?
C9 C8 C1 121.41(15) . . ?
C13 C8 C1 120.29(15) . . ?
C10 C9 C8 120.11(16) . . ?
C9 C10 C11 120.63(17) . . ?
C12 C11 C10 120.26(17) . . ?
C13 C12 C11 120.11(17) . . ?
C12 C13 C8 120.60(16) . . ?
C19 C14 C15 118.42(16) . . ?
C19 C14 C1 121.54(15) . . ?
C15 C14 C1 120.04(15) . . ?
C16 C15 C14 120.49(18) . . ?
C15 C16 C17 119.85(18) . . ?
C18 C17 C16 120.89(18) . . ?
C19 C18 C17 120.04(19) . . ?
C18 C19 C14 120.29(17) . . ?
C5' C1' C2' 108.14(14) . . ?
C5' C1' C6' 125.37(15) . . ?
C2' C1' C6' 126.46(14) . . ?
C1' C2' C3' 107.74(14) . . ?
C1' C2' C7' 126.99(15) . . ?
C3' C2' C7' 125.27(15) . . ?
C4' C3' C2' 107.92(14) . . ?
C4' C3' C8' 124.47(15) . . ?
C2' C3' C8' 127.60(15) . . ?
C5' C4' C3' 108.28(14) . . ?
C5' C4' C9' 127.13(15) . . ?
C3' C4' C9' 124.58(15) . . ?
C4' C5' C1' 107.92(14) . . ?
C4' C5' C10' 125.96(15) . . ?
C1' C5' C10' 126.10(15) . . ?
N1' C6' C1' 179.02(19) . . ?
N2' C7' C2' 178.96(19) . . ?
N3' C8' C3' 177.58(19) . . ?
N4' C9' C4' 178.1(2) . . ?
N5' C10' C5' 178.9(2) . . ?

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
C8 C1 C2 C7 -28.5(2) . . . . ?
C14 C1 C2 C7 152.69(16) . . . . ?
C8 C1 C2 C3 151.05(16) . . . . ?
C14 C1 C2 C3 -27.8(2) . . . . ?
C7 C2 C3 C4 0.5(2) . . . . ?
C1 C2 C3 C4 -179.00(16) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C2 -0.9(3) . . . . ?
C3 C2 C7 C6 0.2(2) . . . . ?
C1 C2 C7 C6 179.76(16) . . . . ?
C14 C1 C8 C9 146.46(16) . . . . ?
C2 C1 C8 C9 -32.4(2) . . . . ?
C14 C1 C8 C13 -31.3(2) . . . . ?
C2 C1 C8 C13 149.83(15) . . . . ?
C13 C8 C9 C10 1.4(2) . . . . ?
C1 C8 C9 C10 -176.46(16) . . . . ?
C8 C9 C10 C11 -1.4(3) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C8 -0.5(3) . . . . ?
C9 C8 C13 C12 -0.4(2) . . . . ?
C1 C8 C13 C12 177.45(16) . . . . ?
C8 C1 C14 C19 145.94(16) . . . . ?
C2 C1 C14 C19 -35.2(2) . . . . ?
C8 C1 C14 C15 -34.7(2) . . . . ?
C2 C1 C14 C15 144.18(16) . . . . ?
C19 C14 C15 C16 0.5(3) . . . . ?
C1 C14 C15 C16 -178.89(16) . . . . ?
C14 C15 C16 C17 -1.1(3) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C17 C18 C19 C14 -1.4(3) . . . . ?
C15 C14 C19 C18 0.7(3) . . . . ?
C1 C14 C19 C18 -179.87(16) . . . . ?
C5' C1' C2' C3' 0.42(18) . . . . ?
C6' C1' C2' C3' -178.07(16) . . . . ?
C5' C1' C2' C7' -179.32(16) . . . . ?
C6' C1' C2' C7' 2.2(3) . . . . ?
C1' C2' C3' C4' -0.18(18) . . . . ?
C7' C2' C3' C4' 179.57(16) . . . . ?
C1' C2' C3' C8' 178.68(16) . . . . ?
C7' C2' C3' C8' -1.6(3) . . . . ?
C2' C3' C4' C5' -0.13(18) . . . . ?
C8' C3' C4' C5' -179.03(15) . . . . ?
C2' C3' C4' C9' 179.23(15) . . . . ?
C8' C3' C4' C9' 0.3(3) . . . . ?
C3' C4' C5' C1' 0.39(18) . . . . ?
C9' C4' C5' C1' -178.95(16) . . . . ?
C3' C4' C5' C10' -177.86(15) . . . . ?
C9' C4' C5' C10' 2.8(3) . . . . ?
C2' C1' C5' C4' -0.50(18) . . . . ?
C6' C1' C5' C4' 178.01(15) . . . . ?
C2' C1' C5' C10' 177.74(16) . . . . ?
C6' C1' C5' C10' -3.7(3) . . . . ?
C5' C1' C6' N1' -21(12) . . . . ?
C2' C1' C6' N1' 157(12) . . . . ?
C1' C2' C7' N2' 156(12) . . . . ?
C3' C2' C7' N2' -23(12) . . . . ?
C4' C3' C8' N3' 5(5) . . . . ?
C2' C3' C8' N3' -174(100) . . . . ?
C5' C4' C9' N4' 158(6) . . . . ?
C3' C4' C9' N4' -22(6) . . . . ?
C4' C5' C10' N5' 80(12) . . . . ?
C1' C5' C10' N5' -97(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.035

data_cr14fdd2
_database_code_depnum_ccdc_archive 'CCDC 227125'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 N5 Si'
_chemical_formula_weight         305.42

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   23.680(4)
_cell_length_b                   14.653(2)
_cell_length_c                   20.072(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6964.6(18)
_cell_formula_units_Z            16
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       'Frag. prism'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2560
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   SADABS
_exptl_absorpt_correction_T_min  0.9455
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-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            9993
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2822
_reflns_number_gt                2444
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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^)+(0.0808P)^2^+4.8998P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(19)
_refine_ls_number_reflns         2822
_refine_ls_number_parameters     202
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1288
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.07397(10) 0.09893(17) 0.49937(15) 0.0403(5) Uani 1 1 d . . .
C2 C 0.07115(10) 0.00214(17) 0.50188(15) 0.0402(5) Uani 1 1 d . . .
C3 C 0.07188(9) -0.02345(18) 0.56904(17) 0.0416(6) Uani 1 1 d . . .
C4 C 0.07464(11) 0.05575(19) 0.60830(16) 0.0443(6) Uani 1 1 d . . .
C5 C 0.07592(10) 0.13195(18) 0.56580(16) 0.0430(6) Uani 1 1 d . . .
C6 C 0.07231(10) 0.15309(18) 0.44209(15) 0.0422(6) Uani 1 1 d . . .
C7 C 0.06303(10) -0.05650(19) 0.44651(16) 0.0447(6) Uani 1 1 d . . .
C8 C 0.06832(12) -0.1142(2) 0.59467(17) 0.0527(7) Uani 1 1 d . . .
C9 C 0.07411(13) 0.0585(2) 0.67941(19) 0.0578(8) Uani 1 1 d . . .
C10 C 0.07865(13) 0.2253(2) 0.58534(17) 0.0541(7) Uani 1 1 d . . .
N1 N 0.07012(10) 0.19799(15) 0.39556(13) 0.0463(6) Uani 1 1 d . . .
N2 N 0.05476(12) -0.1035(2) 0.40207(17) 0.0633(7) Uani 1 1 d . . .
N3 N 0.06567(14) -0.1855(2) 0.6167(2) 0.0770(10) Uani 1 1 d . . .
N4 N 0.07294(15) 0.0585(3) 0.73630(18) 0.0860(11) Uani 1 1 d . . .
N5 N 0.08180(15) 0.3002(2) 0.6006(2) 0.0771(9) Uani 1 1 d . . .
Si1 Si 0.06015(4) 0.27350(6) 0.32308(5) 0.0534(2) Uani 1 1 d . . .
C11 C 0.0347(2) 0.3795(3) 0.3647(3) 0.0892(13) Uani 1 1 d . . .
H11A H 0.0642 0.4014 0.3950 0.107 Uiso 1 1 calc R . .
H11B H 0.0288 0.4265 0.3307 0.107 Uiso 1 1 calc R . .
C12 C -0.0191(3) 0.3682(4) 0.4037(3) 0.118(2) Uani 1 1 d . . .
H12A H -0.0335 0.4278 0.4161 0.177 Uiso 1 1 calc R . .
H12B H -0.0116 0.3328 0.4435 0.177 Uiso 1 1 calc R . .
H12C H -0.0468 0.3368 0.3765 0.177 Uiso 1 1 calc R . .
C13 C 0.13096(19) 0.2814(3) 0.2853(2) 0.0842(12) Uani 1 1 d . . .
H13A H 0.1411 0.2210 0.2681 0.101 Uiso 1 1 calc R . .
H13B H 0.1288 0.3229 0.2471 0.101 Uiso 1 1 calc R . .
C14 C 0.17704(19) 0.3129(4) 0.3293(4) 0.1044(17) Uani 1 1 d . . .
H14A H 0.2113 0.3208 0.3034 0.157 Uiso 1 1 calc R . .
H14C H 0.1835 0.2680 0.3640 0.157 Uiso 1 1 calc R . .
H14D H 0.1666 0.3706 0.3495 0.157 Uiso 1 1 calc R . .
C15 C 0.0061(2) 0.2160(3) 0.2717(2) 0.0918(13) Uani 1 1 d . . .
H15A H -0.0293 0.2153 0.2968 0.110 Uiso 1 1 calc R . .
H15B H -0.0002 0.2530 0.2317 0.110 Uiso 1 1 calc R . .
C16 C 0.0183(4) 0.1233(4) 0.2507(3) 0.147(3) Uani 1 1 d . . .
H16B H -0.0077 0.1057 0.2156 0.220 Uiso 1 1 calc R . .
H16C H 0.0141 0.0823 0.2883 0.220 Uiso 1 1 calc R . .
H16D H 0.0567 0.1199 0.2340 0.220 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 0.0417(12) 0.0417(12) 0.0375(14) 0.0043(12) -0.0024(10) -0.0031(9)
C2 0.0407(12) 0.0389(12) 0.0411(14) 0.0050(11) -0.0028(11) -0.0012(10)
C3 0.0395(11) 0.0419(12) 0.0433(15) 0.0092(12) -0.0037(13) -0.0031(10)
C4 0.0444(13) 0.0495(14) 0.0390(16) 0.0055(12) -0.0021(11) -0.0081(11)
C5 0.0459(12) 0.0446(13) 0.0384(14) 0.0039(12) -0.0034(12) -0.0076(10)
C6 0.0435(12) 0.0392(12) 0.0440(16) 0.0018(12) -0.0002(11) 0.0006(10)
C7 0.0417(12) 0.0448(14) 0.0476(18) 0.0028(13) 0.0029(12) 0.0021(10)
C8 0.0545(15) 0.0505(16) 0.0531(19) 0.0127(14) -0.0008(13) -0.0043(12)
C9 0.0614(17) 0.0676(19) 0.044(2) 0.0070(15) -0.0022(14) -0.0149(14)
C10 0.0622(16) 0.0490(16) 0.0512(19) 0.0035(13) -0.0058(14) -0.0100(12)
N1 0.0614(14) 0.0419(12) 0.0354(13) 0.0092(11) 0.0026(10) 0.0030(9)
N2 0.0616(15) 0.0660(16) 0.0624(19) -0.0195(15) 0.0016(13) -0.0034(12)
N3 0.090(2) 0.0565(17) 0.085(3) 0.0287(18) 0.0036(17) -0.0081(14)
N4 0.103(3) 0.113(3) 0.0421(19) 0.0059(18) 0.0004(16) -0.026(2)
N5 0.092(2) 0.0522(16) 0.087(3) -0.0098(15) -0.0064(18) -0.0122(14)
Si1 0.0682(5) 0.0521(4) 0.0399(4) 0.0138(4) 0.0019(4) 0.0020(4)
C11 0.124(4) 0.063(2) 0.081(3) 0.014(2) 0.014(3) 0.028(2)
C12 0.138(4) 0.105(4) 0.111(5) 0.015(3) 0.049(4) 0.044(3)
C13 0.083(3) 0.107(3) 0.062(3) 0.021(2) 0.0126(19) 0.001(2)
C14 0.082(3) 0.124(4) 0.107(5) 0.015(4) -0.002(3) -0.021(2)
C15 0.118(4) 0.096(3) 0.061(2) 0.021(2) -0.013(2) -0.015(3)
C16 0.230(8) 0.128(5) 0.083(4) -0.028(4) 0.003(5) -0.054(5)

_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 C6 1.398(4) . ?
C1 C5 1.419(4) . ?
C1 C2 1.421(4) . ?
C2 C3 1.399(4) . ?
C2 C7 1.418(4) . ?
C3 C4 1.404(4) . ?
C3 C8 1.428(4) . ?
C4 C5 1.406(4) . ?
C4 C9 1.428(5) . ?
C5 C10 1.425(4) . ?
C6 N1 1.144(4) . ?
C7 N2 1.144(4) . ?
C8 N3 1.137(4) . ?
C9 N4 1.142(5) . ?
C10 N5 1.141(4) . ?
N1 Si1 1.843(2) . ?
Si1 C13 1.844(4) . ?
Si1 C15 1.847(5) . ?
Si1 C11 1.864(4) . ?
C11 C12 1.502(7) . ?
C13 C14 1.478(7) . ?
C15 C16 1.451(8) . ?

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
C6 C1 C5 125.5(2) . . ?
C6 C1 C2 126.5(3) . . ?
C5 C1 C2 108.0(2) . . ?
C3 C2 C7 126.5(2) . . ?
C3 C2 C1 107.5(3) . . ?
C7 C2 C1 125.7(3) . . ?
C2 C3 C4 108.6(2) . . ?
C2 C3 C8 126.6(3) . . ?
C4 C3 C8 124.7(3) . . ?
C3 C4 C5 108.5(3) . . ?
C3 C4 C9 125.7(3) . . ?
C5 C4 C9 125.8(3) . . ?
C4 C5 C1 107.4(2) . . ?
C4 C5 C10 126.6(3) . . ?
C1 C5 C10 126.0(3) . . ?
N1 C6 C1 178.9(3) . . ?
N2 C7 C2 177.9(3) . . ?
N3 C8 C3 178.2(4) . . ?
N4 C9 C4 178.1(4) . . ?
N5 C10 C5 178.8(4) . . ?
C6 N1 Si1 174.8(2) . . ?
N1 Si1 C13 104.22(16) . . ?
N1 Si1 C15 104.83(16) . . ?
C13 Si1 C15 115.4(2) . . ?
N1 Si1 C11 100.80(17) . . ?
C13 Si1 C11 115.3(2) . . ?
C15 Si1 C11 114.0(3) . . ?
C12 C11 Si1 114.6(4) . . ?
C14 C13 Si1 116.4(4) . . ?
C16 C15 Si1 116.9(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
C6 C1 C2 C3 -177.6(2) . . . . ?
C5 C1 C2 C3 -0.5(3) . . . . ?
C6 C1 C2 C7 -3.7(4) . . . . ?
C5 C1 C2 C7 173.4(2) . . . . ?
C7 C2 C3 C4 -173.4(2) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C7 C2 C3 C8 4.5(4) . . . . ?
C1 C2 C3 C8 178.3(2) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C8 C3 C4 C5 -178.1(2) . . . . ?
C2 C3 C4 C9 177.6(3) . . . . ?
C8 C3 C4 C9 -0.3(4) . . . . ?
C3 C4 C5 C1 -0.1(3) . . . . ?
C9 C4 C5 C1 -177.9(3) . . . . ?
C3 C4 C5 C10 179.9(3) . . . . ?
C9 C4 C5 C10 2.1(4) . . . . ?
C6 C1 C5 C4 177.5(2) . . . . ?
C2 C1 C5 C4 0.4(3) . . . . ?
C6 C1 C5 C10 -2.5(4) . . . . ?
C2 C1 C5 C10 -179.6(3) . . . . ?
C5 C1 C6 N1 -62(18) . . . . ?
C2 C1 C6 N1 115(17) . . . . ?
C3 C2 C7 N2 87(9) . . . . ?
C1 C2 C7 N2 -86(9) . . . . ?
C2 C3 C8 N3 176(100) . . . . ?
C4 C3 C8 N3 -6(10) . . . . ?
C3 C4 C9 N4 -24(13) . . . . ?
C5 C4 C9 N4 153(13) . . . . ?
C4 C5 C10 N5 108(20) . . . . ?
C1 C5 C10 N5 -72(20) . . . . ?
C1 C6 N1 Si1 -6(20) . . . . ?
C6 N1 Si1 C13 168(3) . . . . ?
C6 N1 Si1 C15 -70(3) . . . . ?
C6 N1 Si1 C11 48(3) . . . . ?
N1 Si1 C11 C12 -60.1(4) . . . . ?
C13 Si1 C11 C12 -171.6(4) . . . . ?
C15 Si1 C11 C12 51.6(5) . . . . ?
N1 Si1 C13 C14 -55.8(4) . . . . ?
C15 Si1 C13 C14 -170.2(4) . . . . ?
C11 Si1 C13 C14 53.7(5) . . . . ?
N1 Si1 C15 C16 -56.7(5) . . . . ?
C13 Si1 C15 C16 57.3(5) . . . . ?
C11 Si1 C15 C16 -165.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.051

data_cr161m
_database_code_depnum_ccdc_archive 'CCDC 227126'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 N5 Si'
_chemical_formula_weight         347.50

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.7909(15)
_cell_length_b                   10.198(2)
_cell_length_c                   13.425(3)
_cell_angle_alpha                75.481(3)
_cell_angle_beta                 74.317(3)
_cell_angle_gamma                84.171(4)
_cell_volume                     993.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       'Frag. of prism'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   SADABS
_exptl_absorpt_correction_T_min  0.9551
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-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            7359
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         24.71
_reflns_number_total             3367
_reflns_number_gt                2817
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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^)+(0.0650P)^2^+0.2984P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3367
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.5076(2) 0.17349(18) 0.59141(14) 0.0325(4) Uani 1 1 d . . .
C2 C 0.5733(2) 0.23735(18) 0.48246(14) 0.0330(4) Uani 1 1 d . . .
C3 C 0.7007(2) 0.14843(18) 0.43654(14) 0.0340(4) Uani 1 1 d . . .
C4 C 0.7136(2) 0.03030(18) 0.51627(14) 0.0333(4) Uani 1 1 d . . .
C5 C 0.5952(2) 0.04435(18) 0.61151(14) 0.0331(4) Uani 1 1 d . . .
C6 C 0.3725(2) 0.22254(18) 0.66662(14) 0.0329(4) Uani 1 1 d . . .
C7 C 0.5190(3) 0.3676(2) 0.42892(15) 0.0392(4) Uani 1 1 d . . .
C8 C 0.8022(3) 0.1688(2) 0.32825(16) 0.0410(5) Uani 1 1 d . . .
C9 C 0.8276(3) -0.0857(2) 0.50047(15) 0.0384(4) Uani 1 1 d . . .
C10 C 0.5663(3) -0.0541(2) 0.71021(16) 0.0397(4) Uani 1 1 d . . .
N1 N 0.2599(2) 0.25834(15) 0.73015(12) 0.0369(4) Uani 1 1 d . . .
N2 N 0.4763(3) 0.47269(19) 0.38585(15) 0.0554(5) Uani 1 1 d . . .
N3 N 0.8848(3) 0.1807(2) 0.24231(15) 0.0638(6) Uani 1 1 d . . .
N4 N 0.9193(3) -0.17730(19) 0.48580(16) 0.0565(5) Uani 1 1 d . . .
N5 N 0.5434(3) -0.1342(2) 0.78864(15) 0.0617(5) Uani 1 1 d . . .
Si1 Si 0.07313(6) 0.32123(5) 0.82487(4) 0.03240(17) Uani 1 1 d . . .
C11 C -0.0856(3) 0.1803(2) 0.87168(16) 0.0450(5) Uani 1 1 d . . .
H11 H -0.0148 0.0953 0.8890 0.050(6) Uiso 1 1 calc R . .
C12 C -0.1785(4) 0.1637(3) 0.7897(2) 0.0710(8) Uani 1 1 d . . .
H12A H -0.2472 0.0823 0.8172 0.088(9) Uiso 1 1 calc R . .
H12B H -0.0900 0.1564 0.7246 0.079(8) Uiso 1 1 calc R . .
H12C H -0.2577 0.2418 0.7750 0.103(12) Uiso 1 1 calc R . .
C13 C -0.2243(3) 0.1936(3) 0.97554(18) 0.0588(6) Uani 1 1 d . . .
H13A H -0.2934 0.2779 0.9627 0.069(8) Uiso 1 1 calc R . .
H13B H -0.1633 0.1933 1.0298 0.083(9) Uiso 1 1 calc R . .
H13C H -0.3032 0.1181 0.9994 0.070(7) Uiso 1 1 calc R . .
C14 C 0.1762(3) 0.3389(2) 0.93110(15) 0.0432(5) Uani 1 1 d . . .
H14 H 0.0788 0.3677 0.9869 0.050(6) Uiso 1 1 calc R . .
C15 C 0.2527(4) 0.2037(3) 0.9840(2) 0.0653(7) Uani 1 1 d . . .
H15A H 0.3461 0.1699 0.9313 0.063(7) Uiso 1 1 calc R . .
H15B H 0.1587 0.1389 1.0143 0.090(10) Uiso 1 1 calc R . .
H15C H 0.3018 0.2165 1.0398 0.098(10) Uiso 1 1 calc R . .
C16 C 0.3149(3) 0.4488(3) 0.89275(19) 0.0625(7) Uani 1 1 d . . .
H16A H 0.3655 0.4519 0.9507 0.080(8) Uiso 1 1 calc R . .
H16B H 0.2582 0.5361 0.8692 0.098(11) Uiso 1 1 calc R . .
H16C H 0.4089 0.4282 0.8341 0.072(8) Uiso 1 1 calc R . .
C17 C 0.0121(3) 0.4853(2) 0.74154(15) 0.0416(5) Uani 1 1 d . . .
H17 H 0.1072 0.5479 0.7325 0.061(7) Uiso 1 1 calc R . .
C18 C -0.1604(3) 0.5473(3) 0.8007(2) 0.0609(6) Uani 1 1 d . . .
H18A H -0.1790 0.6391 0.7616 0.094(10) Uiso 1 1 calc R . .
H18B H -0.1516 0.5487 0.8712 0.088(9) Uiso 1 1 calc R . .
H18C H -0.2601 0.4933 0.8070 0.078(9) Uiso 1 1 calc R . .
C19 C 0.0053(4) 0.4829(3) 0.62977(18) 0.0656(7) Uani 1 1 d . . .
H19A H -0.0885 0.4246 0.6340 0.096(11) Uiso 1 1 calc R . .
H19B H 0.1190 0.4486 0.5926 0.092(10) Uiso 1 1 calc R . .
H19C H -0.0187 0.5741 0.5914 0.085(9) 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 0.0295(9) 0.0337(10) 0.0354(9) -0.0140(8) -0.0045(7) -0.0009(7)
C2 0.0317(9) 0.0331(10) 0.0345(9) -0.0122(7) -0.0047(7) -0.0020(7)
C3 0.0309(9) 0.0364(10) 0.0361(9) -0.0147(8) -0.0039(7) -0.0044(8)
C4 0.0290(9) 0.0337(10) 0.0405(10) -0.0156(8) -0.0085(7) 0.0000(7)
C5 0.0304(9) 0.0350(10) 0.0368(9) -0.0124(8) -0.0094(7) -0.0020(7)
C6 0.0349(10) 0.0298(9) 0.0336(9) -0.0066(7) -0.0082(8) -0.0033(8)
C7 0.0393(11) 0.0406(12) 0.0357(10) -0.0129(9) -0.0029(8) -0.0012(9)
C8 0.0393(11) 0.0415(11) 0.0418(11) -0.0161(9) -0.0039(9) -0.0020(9)
C9 0.0338(10) 0.0395(11) 0.0438(11) -0.0152(9) -0.0078(8) -0.0011(9)
C10 0.0372(11) 0.0431(11) 0.0400(11) -0.0125(9) -0.0102(8) 0.0007(9)
N1 0.0395(9) 0.0334(8) 0.0323(8) -0.0074(7) -0.0012(7) 0.0022(7)
N2 0.0630(12) 0.0454(11) 0.0494(11) -0.0051(9) -0.0079(9) 0.0040(9)
N3 0.0662(13) 0.0730(14) 0.0443(11) -0.0204(10) 0.0064(10) -0.0061(11)
N4 0.0529(11) 0.0477(11) 0.0679(12) -0.0227(9) -0.0097(9) 0.0112(9)
N5 0.0642(13) 0.0659(13) 0.0467(11) -0.0004(10) -0.0126(9) -0.0011(10)
Si1 0.0314(3) 0.0360(3) 0.0281(3) -0.0098(2) -0.0037(2) 0.0019(2)
C11 0.0428(11) 0.0471(12) 0.0416(11) -0.0105(9) -0.0024(9) -0.0084(9)
C12 0.0753(18) 0.086(2) 0.0576(15) -0.0248(14) -0.0069(14) -0.0373(17)
C13 0.0478(13) 0.0727(17) 0.0486(13) -0.0126(11) 0.0037(10) -0.0164(12)
C14 0.0385(11) 0.0595(13) 0.0320(10) -0.0148(9) -0.0065(8) 0.0004(9)
C15 0.0634(16) 0.0800(18) 0.0521(14) -0.0037(13) -0.0271(12) 0.0034(14)
C16 0.0577(15) 0.0870(19) 0.0502(13) -0.0225(13) -0.0135(12) -0.0206(14)
C17 0.0435(11) 0.0376(11) 0.0432(11) -0.0116(8) -0.0109(9) 0.0055(9)
C18 0.0568(15) 0.0578(15) 0.0683(16) -0.0241(12) -0.0156(12) 0.0201(12)
C19 0.090(2) 0.0601(15) 0.0433(13) -0.0068(11) -0.0246(12) 0.0218(15)

_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 C6 1.396(2) . ?
C1 C2 1.418(3) . ?
C1 C5 1.418(3) . ?
C2 C3 1.398(2) . ?
C2 C7 1.425(3) . ?
C3 C4 1.412(3) . ?
C3 C8 1.429(3) . ?
C4 C5 1.391(2) . ?
C4 C9 1.429(3) . ?
C5 C10 1.426(3) . ?
C6 N1 1.147(2) . ?
C7 N2 1.147(3) . ?
C8 N3 1.142(3) . ?
C9 N4 1.142(2) . ?
C10 N5 1.142(3) . ?
N1 Si1 1.8344(16) . ?
Si1 C17 1.861(2) . ?
Si1 C11 1.865(2) . ?
Si1 C14 1.868(2) . ?
C11 C12 1.521(3) . ?
C11 C13 1.543(3) . ?
C14 C15 1.527(3) . ?
C14 C16 1.532(3) . ?
C17 C19 1.522(3) . ?
C17 C18 1.530(3) . ?

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
C6 C1 C2 127.17(16) . . ?
C6 C1 C5 124.41(16) . . ?
C2 C1 C5 108.31(15) . . ?
C3 C2 C1 107.38(16) . . ?
C3 C2 C7 126.06(16) . . ?
C1 C2 C7 126.57(16) . . ?
C2 C3 C4 108.15(15) . . ?
C2 C3 C8 127.56(18) . . ?
C4 C3 C8 124.28(17) . . ?
C5 C4 C3 108.94(16) . . ?
C5 C4 C9 125.82(17) . . ?
C3 C4 C9 125.23(17) . . ?
C4 C5 C1 107.22(16) . . ?
C4 C5 C10 126.04(17) . . ?
C1 C5 C10 126.74(17) . . ?
N1 C6 C1 177.65(19) . . ?
N2 C7 C2 179.5(2) . . ?
N3 C8 C3 177.8(2) . . ?
N4 C9 C4 178.7(2) . . ?
N5 C10 C5 179.2(2) . . ?
C6 N1 Si1 176.29(15) . . ?
N1 Si1 C17 101.73(8) . . ?
N1 Si1 C11 103.18(8) . . ?
C17 Si1 C11 119.34(10) . . ?
N1 Si1 C14 103.29(8) . . ?
C17 Si1 C14 114.22(10) . . ?
C11 Si1 C14 112.29(9) . . ?
C12 C11 C13 110.32(19) . . ?
C12 C11 Si1 114.78(16) . . ?
C13 C11 Si1 110.91(15) . . ?
C15 C14 C16 111.28(19) . . ?
C15 C14 Si1 111.91(16) . . ?
C16 C14 Si1 113.25(14) . . ?
C19 C17 C18 111.30(19) . . ?
C19 C17 Si1 116.00(15) . . ?
C18 C17 Si1 110.75(15) . . ?

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 -176.71(17) . . . . ?
C5 C1 C2 C3 -0.4(2) . . . . ?
C6 C1 C2 C7 2.7(3) . . . . ?
C5 C1 C2 C7 179.09(17) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C7 C2 C3 C4 -179.36(17) . . . . ?
C1 C2 C3 C8 179.69(18) . . . . ?
C7 C2 C3 C8 0.2(3) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C8 C3 C4 C5 -179.41(17) . . . . ?
C2 C3 C4 C9 178.97(17) . . . . ?
C8 C3 C4 C9 -0.6(3) . . . . ?
C3 C4 C5 C1 -0.4(2) . . . . ?
C9 C4 C5 C1 -179.18(17) . . . . ?
C3 C4 C5 C10 178.79(17) . . . . ?
C9 C4 C5 C10 0.0(3) . . . . ?
C6 C1 C5 C4 176.96(17) . . . . ?
C2 C1 C5 C4 0.5(2) . . . . ?
C6 C1 C5 C10 -2.2(3) . . . . ?
C2 C1 C5 C10 -178.73(17) . . . . ?
C2 C1 C6 N1 149(5) . . . . ?
C5 C1 C6 N1 -27(5) . . . . ?
C3 C2 C7 N2 -77(28) . . . . ?
C1 C2 C7 N2 103(28) . . . . ?
C2 C3 C8 N3 -165(6) . . . . ?
C4 C3 C8 N3 14(6) . . . . ?
C5 C4 C9 N4 168(9) . . . . ?
C3 C4 C9 N4 -10(9) . . . . ?
C4 C5 C10 N5 -35(15) . . . . ?
C1 C5 C10 N5 144(15) . . . . ?
C1 C6 N1 Si1 -118(4) . . . . ?
C6 N1 Si1 C17 -31(2) . . . . ?
C6 N1 Si1 C11 93(2) . . . . ?
C6 N1 Si1 C14 -150(2) . . . . ?
N1 Si1 C11 C12 -71.32(19) . . . . ?
C17 Si1 C11 C12 40.5(2) . . . . ?
C14 Si1 C11 C12 178.12(18) . . . . ?
N1 Si1 C11 C13 162.81(15) . . . . ?
C17 Si1 C11 C13 -85.40(17) . . . . ?
C14 Si1 C11 C13 52.25(19) . . . . ?
N1 Si1 C14 C15 -60.47(17) . . . . ?
C17 Si1 C14 C15 -170.07(15) . . . . ?
C11 Si1 C14 C15 50.02(18) . . . . ?
N1 Si1 C14 C16 66.28(17) . . . . ?
C17 Si1 C14 C16 -43.31(19) . . . . ?
C11 Si1 C14 C16 176.77(16) . . . . ?
N1 Si1 C17 C19 43.8(2) . . . . ?
C11 Si1 C17 C19 -68.7(2) . . . . ?
C14 Si1 C17 C19 154.38(18) . . . . ?
N1 Si1 C17 C18 171.93(15) . . . . ?
C11 Si1 C17 C18 59.36(18) . . . . ?
C14 Si1 C17 C18 -77.52(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.71
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.043