# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2001

data_bm
_database_code_CSD                  169831

_journal_coden_Cambridge      207

_publ_requested_journal       'Perkin Transactions 1'

loop_
_publ_author_name
'Abell, Andrew D.'
'May, Barnaby C. H.'

_publ_contact_author_name     	'Andrew D Abell'  
_publ_contact_author_address 
;
University of Canterbury
Christchurch
NEW ZEALAND
;

_publ_contact_author_email       'A.ABELL@CHEM.CANTERBURY.AC.NZ'

_publ_section_title		
;
(-Methylene tetrazole-based peptidomimetics:Synthesis and inhibition
of HIV protease.
;


_audit_creation_method            SHELXL
_chemical_name_systematic
;
?
;
_chemical_name_common             'N-Z-hPhe-[CN4]-Gly-OBn'
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C27 H27 N5 O4'
_chemical_formula_weight          485.54
_chemical_melting_point           ?
_chemical_compound_source         ?

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    'P1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                    5.0379(3)
_cell_length_b                    10.1066(7)
_cell_length_c                    12.7865(9)
_cell_angle_alpha                 83.577(2)
_cell_angle_beta                  81.897(2)
_cell_angle_gamma                 76.475(2)
_cell_volume                      624.55(7)
_cell_formula_units_Z             1
_cell_measurement_temperature     160(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?

_exptl_crystal_description        'thin plate'
_exptl_crystal_colour             'colourless'
_exptl_crystal_size_max           '0.8'
_exptl_crystal_size_mid           '0.4'
_exptl_crystal_size_min           '0.02'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.291
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              256
_exptl_absorpt_coefficient_mu     0.089
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?

_exptl_special_details
;
?
;

_diffrn_ambient_temperature       160(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        ?
_diffrn_measurement_method        'w scan'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             2198
_diffrn_reflns_av_R_equivalents   0.1010
_diffrn_reflns_av_sigmaI/netI     0.0432
_diffrn_reflns_limit_h_min        -1
_diffrn_reflns_limit_h_max        5
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          3.23
_diffrn_reflns_theta_max          25.61
_reflns_number_total              1867
_reflns_number_observed           1674
_reflns_observed_criterion        >2sigma(I)

_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics     ? 
_computing_publication_material   ? 

_refine_special_details 
; 
Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ 
or flagged by the user for potential systematic errors.  Weighted R-factors 
wR and all goodnesses 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 observed criterion 
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0642P)^2^+0.0616P] 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     ? 
_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    0.64(158) 
_refine_ls_number_reflns          1867 
_refine_ls_number_parameters      365 
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.0427 
_refine_ls_R_factor_obs           0.0359 
_refine_ls_wR_factor_all          0.0957 
_refine_ls_wR_factor_obs          0.0898 
_refine_ls_goodness_of_fit_all    1.064 
_refine_ls_goodness_of_fit_obs    1.068 
_refine_ls_restrained_S_all       1.062 
_refine_ls_restrained_S_obs       1.067 
_refine_ls_shift/esd_max          0.020 
_refine_ls_shift/esd_mean         0.003 

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_thermal_displace_type 
_atom_site_occupancy
_atom_site_calc_flag 
_atom_site_refinement_flags 
_atom_site_disorder_group 
O1 O 0.0361(4) 0.6771(3) 0.2871(2) 0.0364(6) Uani 1 d . . 
O4 O 0.3204(5) 0.9310(3) 0.1382(2) 0.0433(7) Uani 1 d . . 
N2 N 0.0007(6) 1.1371(3) 0.3526(3) 0.0363(7) Uani 1 d . . 
O2 O -0.3419(5) 0.7666(3) 0.3970(2) 0.0410(7) Uani 1 d . . 
N1 N 0.0844(5) 0.7943(3) 0.4169(2) 0.0314(7) Uani 1 d . . 
H1A H 0.2492(5) 0.7936(3) 0.3829(2) 0.038 Uiso 1 calc R . 
C13 C -0.0952(6) 0.7475(4) 0.3698(3) 0.0302(8) Uani 1 d . . 
N3 N -0.2038(6) 1.2406(3) 0.3207(3) 0.0457(9) Uani 1 d . . 
N5 N -0.3150(6) 1.1677(3) 0.4853(3) 0.0434(8) Uani 1 d . . 
C1 C 0.0175(6) 0.8459(4) 0.5213(3) 0.0323(8) Uani 1 d . . 
H1 H -0.1857(6) 0.8600(4) 0.5411(3) 0.039 Uiso 1 calc R . 
C14 C -0.1329(7) 0.6161(4) 0.2325(3) 0.0430(10) Uani 1 d . . 
H14B H -0.2722(7) 0.6881(4) 0.1991(3) 0.052 Uiso 1 calc R . 
H14A H -0.2296(7) 0.5566(4) 0.2832(3) 0.052 Uiso 1 calc R . 
N4 N -0.3928(7) 1.2579(4) 0.4017(3) 0.0489(9) Uani 1 d . . 
C15 C 0.0529(7) 0.5339(4) 0.1496(3) 0.0364(9) Uani 1 d . . 
C17 C 0.4596(8) 0.3629(4) 0.0985(3) 0.0474(11) Uani 1 d . .
H17 H 0.6239(8) 0.3013(4) 0.1160(3) 0.057 Uiso 1 calc R . 
C2 C 0.0961(7) 0.9833(4) 0.5191(3) 0.0340(9) Uani 1 d . . 
H2B H 0.0725(7) 1.0103(4) 0.5925(3) 0.041 Uiso 1 calc R . 
H2A H 0.2928(7) 0.9730(4) 0.4912(3) 0.041 Uiso 1 calc R . 
O3 O -0.1250(5) 1.0024(3) 0.2001(2) 0.0533(8) Uani 1 d . . 
C16 C 0.2928(8) 0.4424(4) 0.1744(3) 0.0425(10) Uani 1 d . . 
H16 H 0.3429(8) 0.4344(4) 0.2441(3) 0.051 Uiso 1 calc R . 
C3 C -0.0709(7) 1.0942(4) 0.4528(3) 0.0321(8) Uani 1 d . . 
C5 C 0.1124(7) 0.9995(4) 0.2010(3) 0.0372(9) Uani 1 d . . 
C4 C 0.2227(7) 1.0771(4) 0.2741(3) 0.0402(10) Uani 1 d . . 
H4B H 0.3700(7) 1.0142(4) 0.3104(3) 0.048 Uiso 1 calc R . 
H4A H 0.3020(7) 1.1500(4) 0.2321(3) 0.048 Uiso 1 calc R . 
C12 C -0.1691(8) 0.6030(4) 0.6998(3) 0.0453(10) Uani 1 d . . 
H12 H -0.2368(8) 0.6728(4) 0.7470(3) 0.054 Uiso 1 calc R . 
C11 C -0.2868(8) 0.4903(5) 0.7101(4) 0.0548(12) Uani 1 d . . 
H11 H -0.4323(8) 0.4828(5) 0.7648(4) 0.066 Uiso 1 calc R . 
C6 C 0.1598(8) 0.7427(4) 0.6050(3) 0.0393(9) Uani 1 d . . 
H6B H 0.3599(8) 0.7181(4) 0.5818(3) 0.047 Uiso 1 calc R . 
H6A H 0.1324(8) 0.7852(4) 0.6729(3) 0.047 Uiso 1 calc R . 
C7 C 0.0462(7) 0.6148(4) 0.6215(3) 0.0372(9) Uani 1 d . .
C8 C 0.1456(8) 0.5099(4) 0.5546(4) 0.0457(11) Uani 1 d . . 
H8 H 0.2967(8) 0.5148(4) 0.5018(4) 0.055 Uiso 1 calc R . 
C18 C 0.3854(9) 0.3735(6) -0.0031(4) 0.0613(13) Uani 1 d . . 
H18 H 0.4977(9) 0.3184(6) -0.0551(4) 0.074 Uiso 1 calc R . 
C21 C 0.2441(9) 0.8636(5) 0.0548(3) 0.0470(10) Uani 1 d . . 
H21B H 0.0514(9) 0.8540(5) 0.0724(3) 0.056 Uiso 1 calc R 1 
H21A H 0.3639(9) 0.7711(5) 0.0498(3) 0.056 Uiso 1 calc R 1 
C10 C -0.1939(8) 0.3893(5) 0.6414(4) 0.0545(12) Uani 1 d . . 
H10 H -0.2800(8) 0.3142(5) 0.6468(4) 0.065 Uiso 1 calc R . 
C20 C -0.0140(9) 0.5441(5) 0.0476(4) 0.0558(12) Uani 1 d . . 
H20 H -0.1751(9) 0.6072(5) 0.0287(4) 0.067 Uiso 1 calc R . 
C19 C 0.1527(10) 0.4627(6) -0.0279(4) 0.071(2) Uani 1 d . . 
H19 H 0.1026(10) 0.4697(6) -0.0976(4) 0.085 Uiso 1 calc R . 
C9 C 0.0242(9) 0.3975(4) 0.5648(4) 0.0528(12) Uani 1 d . . 
H9 H 0.0924(9) 0.3265(4) 0.5187(4) 0.063 Uiso 1 calc R . 
C22 C 0.2743(8) 0.9457(4) -0.0486(3) 0.0416(10) Uani 0.55(2) d P 1 
C25 C 0.3362(12) 1.1013(7) -0.2411(5) 0.0668(15) Uani 0.55(2) d P 1 
H25 H 0.3607(110) 1.1537(55) -0.3087(43) 0.080 Uiso 0.55(2) d P 1 
C23 C 0.5314(30) 0.9329(15) -0.1117(10) 0.066(4) Uani 0.55(2) d P 1 
H23A H 0.6872(30) 0.8668(15) -0.0915(10) 0.080 Uiso 0.55(2) calc PR 1
C24 C 0.5524(34) 1.0192(19) -0.2041(11) 0.084(5) Uani 0.55(2) d P 1 
H24A H 0.7292(34) 1.0188(19) -0.2417(11) 0.101 Uiso 0.55(2) calc PR 1 
C26 C 0.0762(31) 1.1165(18) -0.1766(12) 0.077(4) Uani 0.55(2) d P 1 
H26A H -0.0781(31) 1.1837(18) -0.1968(12) 0.093 Uiso 0.55(2) calc PR 1 
C27 C 0.0526(26) 1.0304(19) -0.0825(11) 0.069(4) Uani 0.55(2) d P 1 
H27A H -0.1228(26) 1.0328(19) -0.0431(11) 0.083 Uiso 0.55(2) calc PR 1 
C22' C 0.2743(8) 0.9457(4) -0.0486(3) 0.0416(10) Uani 0.45(2) d P 2 
C25' C 0.3362(12) 1.1013(7) -0.2411(5) 0.0668(15) Uani 0.45(2) d P 2 
H25' H 0.3607(110) 1.1537(55) -0.3087(43) 0.080 Uiso 0.45(2) d P 2 
C23' C 0.4237(37) 0.8888(18) -0.1338(11) 0.060(5) Uani 0.45(2) d P 2 
H23B H 0.5075(37) 0.7942(18) -0.1276(11) 0.072 Uiso 0.45(2) calc PR 2 
C24' C 0.4608(33) 0.9623(20) -0.2302(12) 0.063(5) Uani 0.45(2) d P 2 
H24B H 0.5702(33) 0.9187(20) -0.2887(12) 0.075 Uiso 0.45(2) calc PR 2 
C26' C 0.1911(52) 1.1579(17) -0.1618(12) 0.069(5) Uani 0.45(2) d P 2 
H26B H 0.1112(52) 1.2529(17) -0.1690(12) 0.082 Uiso 0.45(2) calc PR 2 
C27' C 0.1460(46) 1.0845(18) -0.0648(11) 0.065(5) Uani 0.45(2) d P 2 
H27B H 0.0268(46) 1.1289(18) -0.0086(11) 0.078 Uiso 0.45(2) calc PR 2 

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 
O1 0.0279(12) 0.042(2) 0.041(2) -0.0109(13) -0.0032(10) -0.0072(10) 
O4 0.0399(14) 0.057(2) 0.031(2) -0.0062(14) -0.0011(11) -0.0066(12) 
N2 0.037(2) 0.033(2) 0.036(2) 0.001(2) -0.0036(12) -0.0042(12) 
O2 0.0240(13) 0.054(2) 0.046(2) -0.0118(13) -0.0027(10) -0.0080(10) 
N1 0.0244(13) 0.038(2) 0.031(2) -0.0062(15) 0.0004(11) -0.0064(12) 
C13 0.024(2) 0.030(2) 0.034(2) 0.000(2) -0.0032(14) -0.0031(13) 
N3 0.048(2) 0.038(2) 0.045(2) 0.002(2) -0.004(2) 0.0004(14) 
N5 0.042(2) 0.040(2) 0.043(2) -0.003(2) 0.0002(14) -0.0029(13) 
C1 0.029(2) 0.031(2) 0.036(2) -0.003(2) -0.0035(14) -0.0058(14) 
C14 0.032(2) 0.057(3) 0.042(2) -0.015(2) -0.008(2) -0.009(2) 
N4 0.048(2) 0.044(2) 0.047(2) -0.002(2) -0.004(2) 0.0032(15) 
C15 0.040(2) 0.033(2) 0.038(3) -0.001(2) -0.003(2) -0.0125(15) 
C17 0.048(2) 0.039(3) 0.047(3) 0.003(2) -0.002(2) 0.002(2) 
C2 0.037(2) 0.035(2) 0.029(2) -0.004(2) -0.0032(14) -0.0050(15)
O3 0.038(2) 0.064(2) 0.059(2) -0.014(2) -0.0072(13) -0.0088(12) 
C16 0.049(2) 0.039(2) 0.038(2) 0.000(2) -0.007(2) -0.007(2) 
C3 0.036(2) 0.027(2) 0.033(2) -0.002(2) -0.0016(14) -0.0090(14) 
C5 0.034(2) 0.042(2) 0.032(2) 0.004(2) -0.0030(14) -0.0048(15) 
C4 0.036(2) 0.046(3) 0.039(3) -0.003(2) 0.000(2) -0.013(2) 
C12 0.053(2) 0.041(3) 0.038(3) 0.005(2) -0.006(2) -0.005(2) 
C11 0.049(2) 0.060(3) 0.048(3) 0.018(3) 0.001(2) -0.011(2) 
C6 0.043(2) 0.038(2) 0.037(2) -0.004(2) -0.008(2) -0.0061(15) 
C7 0.037(2) 0.035(2) 0.038(2) 0.004(2) -0.011(2) -0.0033(15) 
C8 0.041(2) 0.036(3) 0.056(3) 0.001(2) -0.005(2) -0.002(2) 
C18 0.058(3) 0.079(4) 0.042(3) -0.013(3) 0.002(2) -0.004(2) 
C21 0.055(2) 0.050(3) 0.035(3) -0.004(2) -0.003(2) -0.011(2) 
C10 0.050(2) 0.046(3) 0.068(3) 0.006(3) -0.013(2) -0.016(2) 
C20 0.051(2) 0.070(3) 0.041(3) -0.004(2) -0.010(2) 0.001(2) 
C19 0.065(3) 0.101(4) 0.039(3) -0.020(3) -0.011(2) 0.007(3) 
C9 0.053(2) 0.037(3) 0.068(3) -0.003(2) -0.008(2) -0.008(2) 
C22 0.046(2) 0.040(3) 0.039(3) -0.010(2) -0.005(2) -0.007(2) 
C25 0.081(4) 0.084(5) 0.042(4) 0.006(3) -0.011(3) -0.037(3) 
C23 0.060(7) 0.082(9) 0.047(7) 0.007(6) 0.004(5) -0.008(6) 
C24 0.078(9) 0.108(11) 0.062(8) 0.003(8) 0.020(7) -0.033(8)
C26 0.085(9) 0.073(10) 0.069(9) 0.025(7) -0.027(7) -0.009(7) 
C27 0.061(6) 0.083(11) 0.056(7) 0.023(7) -0.007(5) -0.013(6) 
C22' 0.046(2) 0.040(3) 0.039(3) -0.010(2) -0.005(2) -0.007(2) 
C25' 0.081(4) 0.084(5) 0.042(4) 0.006(3) -0.011(3) -0.037(3) 
C23' 0.060(9) 0.050(9) 0.052(9) -0.006(7) 0.004(6) 0.018(6) 
C24' 0.057(8) 0.070(11) 0.045(8) 0.006(7) 0.015(6) -0.001(6) 
C26' 0.114(15) 0.042(8) 0.044(9) -0.011(7) -0.023(8) 0.005(8) 
C27' 0.097(13) 0.043(10) 0.035(8) -0.010(7) 0.005(7) 0.021(7) 

_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 
O1 C13 1.347(4) . ? 
O1 C14 1.450(4) . ? 
O4 C5 1.331(4) . ? 
O4 C21 1.466(5) . ? 
N2 C3 1.334(5) . ? 
N2 N3 1.356(4) . ? 
N2 C4 1.459(4) . ? 
O2 C13 1.218(4) . ? 
N1 C13 1.350(4) . ? 
N1 C1 1.454(4) . ? 
N3 N4 1.302(5) . ? 
N5 C3 1.317(5) . ? 
N5 N4 1.364(5) . ? 
C1 C2 1.527(5) . ? 
C1 C6 1.537(5) . ?
C14 C15 1.498(5) . ? 
C15 C20 1.379(6) . ? 
C15 C16 1.391(5) . ? 
C17 C16 1.386(6) . ? 
C17 C18 1.387(6) . ? 
C2 C3 1.493(5) . ? 
O3 C5 1.191(4) . ? 
C5 C4 1.520(5) . ? 
C12 C7 1.386(5) . ? 
C12 C11 1.389(6) . ? 
C11 C10 1.376(6) . ? 
C6 C7 1.515(5) . ? 
C7 C8 1.393(6) . ? 
C8 C9 1.396(6) . ? 
C18 C19 1.354(7) . ? 
C21 C22' 1.488(6) . ? 
C21 C22 1.488(6) . ? 
C10 C9 1.376(6) . ? 
C20 C19 1.393(6) . ? 
C22 C27 1.333(13) . ?
C22 C23 1.413(12) . ? 
C25 C24 1.32(2) . ? 
C25 C26 1.431(15) . ? 
C23 C24 1.39(2) . ? 
C26 C27 1.41(2) . ? 
C22' C23' 1.338(13) . ? 
C22' C27' 1.41(2) . ? 
C25' C26' 1.27(2) . ? 
C25' C24' 1.40(2) . ? 
C23' C24' 1.38(2) . ? 
C26' C27' 1.39(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
C13 O1 C14 115.8(3) . . ? 
C5 O4 C21 115.9(3) . . ? 
C3 N2 N3 108.8(3) . . ? 
C3 N2 C4 130.9(3) . . ? 
N3 N2 C4 119.3(3) . . ? 
C13 N1 C1 122.9(3) . . ? 
O2 C13 O1 124.3(3) . . ? 
O2 C13 N1 125.3(3) . . ? 
O1 C13 N1 110.4(3) . . ? 
N4 N3 N2 105.9(3) . . ? 
C3 N5 N4 106.1(3) . . ? 
N1 C1 C2 110.4(3) . . ? 
N1 C1 C6 111.1(3) . . ? 
C2 C1 C6 110.8(3) . . ? 
O1 C14 C15 107.7(3) . . ? 
N3 N4 N5 110.5(3) . . ? 
C20 C15 C16 118.4(4) . . ? 
C20 C15 C14 120.8(4) . . ? 
C16 C15 C14 120.8(4) . . ? 
C16 C17 C18 119.7(4) . . ?
C3 C2 C1 113.2(3) . . ? 
C17 C16 C15 120.7(4) . . ? 
N5 C3 N2 108.6(3) . . ? 
N5 C3 C2 124.9(3) . . ? 
N2 C3 C2 126.5(3) . . ? 
O3 C5 O4 126.0(4) . . ? 
O3 C5 C4 124.4(3) . . ? 
O4 C5 C4 109.5(3) . . ? 
N2 C4 C5 109.7(3) . . ? 
C7 C12 C11 120.7(4) . . ? 
C10 C11 C12 120.4(4) . . ? 
C7 C6 C1 111.2(3) . . ? 
C12 C7 C8 118.6(4) . . ? 
C12 C7 C6 120.6(4) . . ? 
C8 C7 C6 120.7(3) . . ? 
C7 C8 C9 120.3(4) . . ? 
C19 C18 C17 119.9(4) . . ? 
O4 C21 C22' 109.7(3) . . ? 
O4 C21 C22 109.7(3) . . ? 
C9 C10 C11 119.7(4) . . ?
C15 C20 C19 120.5(4) . . ? 
C18 C19 C20 120.7(4) . . ? 
C10 C9 C8 120.3(4) . . ? 
C27 C22 C23 119.8(8) . . ? 
C27 C22 C21 118.9(6) . . ? 
C23 C22 C21 121.2(6) . . ? 
C24 C25 C26 118.5(9) . . ? 
C24 C23 C22 118.8(10) . . ? 
C25 C24 C23 122.4(10) . . ? 
C27 C26 C25 119.0(11) . . ? 
C22 C27 C26 120.5(10) . . ? 
C23' C22' C27' 115.6(9) . . ? 
C23' C22' C21 120.9(7) . . ? 
C27' C22' C21 123.4(7) . . ? 
C26' C25' C24' 119.4(10) . . ? 
C22' C23' C24' 122.5(12) . . ? 
C23' C24' C25' 119.5(12) . . ? 
C25' C26' C27' 121.8(13) . . ? 
C26' C27' C22' 121.0(12) . . ? 

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 
C14 O1 C13 O2 -3.3(5) . . . . ? 
C14 O1 C13 N1 177.4(3) . . . . ? 
C1 N1 C13 O2 15.2(5) . . . . ? 
C1 N1 C13 O1 -165.4(3) . . . . ? 
C3 N2 N3 N4 0.0(4) . . . . ? 
C4 N2 N3 N4 169.5(3) . . . . ? 
C13 N1 C1 C2 -131.2(3) . . . . ? 
C13 N1 C1 C6 105.6(3) . . . . ? 
C13 O1 C14 C15 -175.5(3) . . . . ?
N2 N3 N4 N5 0.0(4) . . . . ? 
C3 N5 N4 N3 0.0(4) . . . . ? 
O1 C14 C15 C20 -133.3(4) . . . . ? 
O1 C14 C15 C16 48.7(5) . . . . ? 
N1 C1 C2 C3 66.3(4) . . . . ? 
C6 C1 C2 C3 -170.3(3) . . . . ? 
C18 C17 C16 C15 -0.6(6) . . . . ? 
C20 C15 C16 C17 -0.4(6) . . . . ? 
C14 C15 C16 C17 177.7(4) . . . . ? 
N4 N5 C3 N2 0.0(4) . . . . ? 
N4 N5 C3 C2 179.1(3) . . . . ? 
N3 N2 C3 N5 0.0(4) . . . . ? 
C4 N2 C3 N5 -167.9(3) . . . . ? 
N3 N2 C3 C2 -179.1(3) . . . . ? 
C4 N2 C3 C2 13.0(6) . . . . ? 
C1 C2 C3 N5 83.9(4) . . . . ? 
C1 C2 C3 N2 -97.1(4) . . . . ? 
C21 O4 C5 O3 5.7(5) . . . . ? 
C21 O4 C5 C4 -173.2(3) . . . . ? 
C3 N2 C4 C5 98.2(4) . . . . ?
N3 N2 C4 C5 -68.5(4) . . . . ? 
O3 C5 C4 N2 8.7(5) . . . . ? 
O4 C5 C4 N2 -172.3(3) . . . . ? 
C7 C12 C11 C10 -1.0(6) . . . . ? 
N1 C1 C6 C7 -66.9(4) . . . . ? 
C2 C1 C6 C7 170.0(3) . . . . ? 
C11 C12 C7 C8 -1.3(6) . . . . ? 
C11 C12 C7 C6 175.3(4) . . . . ? 
C1 C6 C7 C12 -92.6(4) . . . . ? 
C1 C6 C7 C8 83.9(4) . . . . ? 
C12 C7 C8 C9 1.9(6) . . . . ? 
C6 C7 C8 C9 -174.6(4) . . . . ? 
C16 C17 C18 C19 0.8(7) . . . . ? 
C5 O4 C21 C22' 102.0(4) . . . . ? 
C5 O4 C21 C22 102.0(4) . . . . ? 
C12 C11 C10 C9 2.6(6) . . . . ? 
C16 C15 C20 C19 1.2(6) . . . . ? 
C14 C15 C20 C19 -176.9(4) . . . . ? 
C17 C18 C19 C20 0.0(8) . . . . ? 
C15 C20 C19 C18 -1.0(8) . . . . ?
C11 C10 C9 C8 -2.0(7) . . . . ? 
C7 C8 C9 C10 -0.3(6) . . . . ? 
O4 C21 C22 C27 -97.6(11) . . . . ? 
C22' C21 C22 C27 0.0(1000) . . . . ? 
O4 C21 C22 C23 83.8(10) . . . . ? 
C22' C21 C22 C23 0.0(1000) . . . . ? 
C27 C22 C23 C24 5.9(17) . . . . ? 
C21 C22 C23 C24 -175.5(10) . . . . ? 
C26 C25 C24 C23 9.1(20) . . . . ? 
C22 C23 C24 C25 -7.9(21) . . . . ? 
C24 C25 C26 C27 -8.3(19) . . . . ? 
C23 C22 C27 C26 -5.6(18) . . . . ? 
C21 C22 C27 C26 175.7(11) . . . . ? 
C25 C26 C27 C22 6.8(21) . . . . ? 
O4 C21 C22' C23' 127.0(13) . . . . ? 
C22 C21 C22' C23' 0.0(1000) . . . . ? 
O4 C21 C22' C27' -54.7(14) . . . . ? 
C22 C21 C22' C27' 0.0(1000) . . . . ? 
C27' C22' C23' C24' 2.9(19) . . . . ? 
C21 C22' C23' C24' -178.7(12) . . . . ?
C22' C23' C24' C25' -0.8(23) . . . . ? 
C26' C25' C24' C23' 0.2(21) . . . . ? 
C24' C25' C26' C27' -1.8(23) . . . . ? 
C25' C26' C27' C22' 4.1(26) . . . . ? 
C23' C22' C27' C26' -4.4(20) . . . . ? 
C21 C22' C27' C26' 177.1(12) . . . . ? 

_refine_diff_density_max    0.169 
_refine_diff_density_min   -0.151 
_refine_diff_density_rms    0.036