# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2008


data_global

_journal_coden_Cambridge         177
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Braja Hazra'
'Samit Chattopadhyay'
'Mukund V. Deshpande'
'Rajesh G. Gonnade'
'Sreenath Kadreppa'
'Vandana S. Pore'
'Fazal Shirazi'
'Namdev S. Vatmurge'

_publ_contact_author_name        'Dr Braja Hazra'
_publ_contact_author_email       BG.HAZRA@NCL.RES.IN

_publ_section_title              
;
Synthesis and biological evaluation of bile acid
dimers linked with 1,2,3-triazole and bis-?-lactam

;

# Attachment 'NSV-3.cif'

data_3
_database_code_depnum_ccdc_archive 'CCDC 690111'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'1,2-Bis[3'-azido-4'-phenylazetidine-2'-one-1'-yl]ethane'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 N8 O2'
_chemical_formula_sum            'C20 H18 N8 O2'
_chemical_formula_weight         402.42

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   13.838(11)
_cell_length_b                   6.873(6)
_cell_length_c                   22.068(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.710(15)
_cell_angle_gamma                90.00
_cell_volume                     2085(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2898
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      28.05

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9503
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_process_details   'bruker sadabs'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(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_device       'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9849
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3667
_reflns_number_gt                2786
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'

_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^)+(0.0597P)^2^+0.4102P] 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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3667
_refine_ls_number_parameters     298
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1433
_refine_ls_wR_factor_gt          0.1327
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.075
_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
O1 O 0.95823(10) 0.1474(2) 0.23049(7) 0.0724(4) Uani 1 1 d . . .
O2 O 1.02427(16) -0.1237(3) 0.07474(8) 0.0987(6) Uani 1 1 d . . .
N1 N 1.07009(11) 0.2743(2) 0.16906(7) 0.0542(4) Uani 1 1 d . . .
N2 N 1.17643(13) 0.0847(3) 0.28525(8) 0.0696(5) Uani 1 1 d . . .
N3 N 1.26252(15) 0.0540(3) 0.29734(9) 0.0758(6) Uani 1 1 d . . .
N4 N 1.34088(19) 0.0361(5) 0.31569(12) 0.1268(11) Uani 1 1 d . . .
N5 N 0.92369(13) 0.1525(2) 0.07424(8) 0.0622(5) Uani 1 1 d . . .
N6 N 0.7767(8) -0.2374(8) 0.0809(3) 0.0921(16) Uani 0.60 1 d PD A 1
N7 N 0.7775(11) -0.2579(11) 0.0262(3) 0.083(2) Uani 0.60 1 d PD A 1
N8 N 0.7655(4) -0.2888(7) -0.0231(2) 0.1360(17) Uani 0.65 1 d PD A 1
N6' N 0.8225(6) -0.2398(15) 0.0506(10) 0.107(4) Uani 0.40 1 d PD A 2
N7' N 0.7358(7) -0.271(2) 0.0441(11) 0.113(5) Uani 0.40 1 d PD A 2
N8' N 0.6579(6) -0.3208(12) 0.0385(6) 0.161(5) Uani 0.35 1 d PD A 2
C1 C 1.03646(14) 0.1581(3) 0.21127(9) 0.0556(5) Uani 1 1 d . . .
C2 C 1.13292(14) 0.0479(3) 0.22259(9) 0.0572(5) Uani 1 1 d . . .
H2 H 1.1276 -0.0905 0.2121 0.069 Uiso 1 1 calc R . .
C3 C 1.16562(13) 0.1787(3) 0.17030(9) 0.0551(5) Uani 1 1 d . . .
H3 H 1.1692 0.1024 0.1331 0.066 Uiso 1 1 calc R . .
C4 C 1.25349(14) 0.3052(3) 0.18369(9) 0.0569(5) Uani 1 1 d . . .
C5 C 1.33917(16) 0.2541(4) 0.16120(12) 0.0737(7) Uani 1 1 d . . .
H5 H 1.3403 0.1462 0.1359 0.088 Uiso 1 1 calc R . .
C6 C 1.42295(17) 0.3613(5) 0.17588(14) 0.0911(8) Uani 1 1 d . . .
H6 H 1.4801 0.3257 0.1604 0.109 Uiso 1 1 calc R . .
C7 C 1.42205(19) 0.5202(5) 0.21335(15) 0.0973(9) Uani 1 1 d . . .
H7 H 1.4786 0.5917 0.2236 0.117 Uiso 1 1 calc R . .
C8 C 1.33794(19) 0.5729(4) 0.23545(14) 0.0923(8) Uani 1 1 d . . .
H8 H 1.3374 0.6811 0.2607 0.111 Uiso 1 1 calc R . .
C9 C 1.25367(16) 0.4679(3) 0.22081(11) 0.0710(6) Uani 1 1 d . . .
H9 H 1.1966 0.5064 0.2359 0.085 Uiso 1 1 calc R . .
C10 C 1.02015(15) 0.4151(3) 0.12810(10) 0.0605(5) Uani 1 1 d . . .
H10A H 1.0643 0.5205 0.1215 0.073 Uiso 1 1 calc R . .
H10B H 0.9659 0.4694 0.1466 0.073 Uiso 1 1 calc R . .
C11 C 0.98268(16) 0.3239(3) 0.06721(10) 0.0641(6) Uani 1 1 d . . .
H11A H 0.9442 0.4189 0.0425 0.077 Uiso 1 1 calc R . .
H11B H 1.0375 0.2881 0.0459 0.077 Uiso 1 1 calc R . .
C12 C 0.9495(2) -0.0381(4) 0.08102(10) 0.0738(7) Uani 1 1 d . A .
C13 C 0.8516(2) -0.0922(4) 0.10135(13) 0.0941(9) Uani 1 1 d D . .
H13 H 0.8640 -0.1084 0.1457 0.113 Uiso 1 1 calc R A 1
C14 C 0.82505(16) 0.1294(3) 0.09106(11) 0.0714(6) Uani 1 1 d . A .
H14 H 0.8180 0.1947 0.1298 0.086 Uiso 1 1 calc R . .
C15 C 0.74409(18) 0.1812(3) 0.04347(12) 0.0749(6) Uani 1 1 d . . .
C16 C 0.7576(2) 0.2106(4) -0.01714(12) 0.0849(7) Uani 1 1 d . A .
H16 H 0.8198 0.2013 -0.0289 0.102 Uiso 1 1 calc R . .
C17 C 0.6804(3) 0.2533(4) -0.06024(15) 0.1030(9) Uani 1 1 d . . .
H17 H 0.6909 0.2749 -0.1006 0.124 Uiso 1 1 calc R A .
C18 C 0.5886(3) 0.2640(5) -0.0438(2) 0.1236(12) Uani 1 1 d . A .
H18 H 0.5363 0.2919 -0.0729 0.148 Uiso 1 1 calc R . .
C19 C 0.5734(3) 0.2336(6) 0.0159(2) 0.1362(13) Uani 1 1 d . . .
H19 H 0.5108 0.2404 0.0272 0.163 Uiso 1 1 calc R A .
C20 C 0.6506(2) 0.1933(5) 0.05893(16) 0.1104(10) Uani 1 1 d . A .
H20 H 0.6397 0.1738 0.0993 0.132 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
O1 0.0594(8) 0.0776(10) 0.0840(10) 0.0099(8) 0.0240(8) -0.0041(7)
O2 0.1395(16) 0.0668(11) 0.0892(13) 0.0000(9) 0.0100(12) 0.0299(11)
N1 0.0507(9) 0.0519(9) 0.0611(10) 0.0033(8) 0.0112(8) -0.0021(7)
N2 0.0564(11) 0.0863(13) 0.0660(11) 0.0017(10) 0.0073(9) 0.0021(9)
N3 0.0657(13) 0.0891(15) 0.0725(13) 0.0042(11) 0.0070(11) 0.0179(11)
N4 0.0776(15) 0.191(3) 0.107(2) -0.004(2) -0.0084(14) 0.0402(18)
N5 0.0758(11) 0.0500(10) 0.0597(10) 0.0034(8) 0.0027(9) -0.0017(8)
N6 0.124(4) 0.082(3) 0.074(3) 0.008(2) 0.025(4) -0.033(3)
N7 0.146(8) 0.051(2) 0.049(3) -0.005(2) 0.000(4) -0.008(5)
N8 0.201(5) 0.102(3) 0.099(3) -0.005(3) -0.008(3) -0.046(3)
N6' 0.093(6) 0.073(5) 0.145(11) -0.025(7) -0.024(7) -0.002(4)
N7' 0.100(9) 0.098(8) 0.130(11) -0.031(9) -0.038(8) 0.021(7)
N8' 0.058(4) 0.100(6) 0.311(15) -0.047(7) -0.038(6) -0.010(4)
C1 0.0556(11) 0.0521(11) 0.0600(12) -0.0022(10) 0.0111(10) -0.0069(9)
C2 0.0579(11) 0.0518(12) 0.0624(12) -0.0012(10) 0.0094(10) -0.0029(9)
C3 0.0534(11) 0.0544(12) 0.0590(11) -0.0060(10) 0.0128(9) -0.0007(9)
C4 0.0513(11) 0.0567(12) 0.0639(12) 0.0018(10) 0.0120(10) -0.0005(9)
C5 0.0607(13) 0.0777(15) 0.0859(16) -0.0045(13) 0.0222(12) 0.0010(11)
C6 0.0506(13) 0.112(2) 0.114(2) 0.0064(19) 0.0217(14) -0.0029(14)
C7 0.0649(15) 0.104(2) 0.121(2) -0.005(2) 0.0027(16) -0.0222(15)
C8 0.0769(16) 0.0816(18) 0.118(2) -0.0198(16) 0.0084(16) -0.0159(14)
C9 0.0607(12) 0.0664(14) 0.0871(16) -0.0108(13) 0.0139(12) -0.0024(11)
C10 0.0608(12) 0.0476(11) 0.0739(14) 0.0058(11) 0.0109(11) -0.0017(9)
C11 0.0711(13) 0.0587(13) 0.0636(13) 0.0144(11) 0.0120(11) 0.0043(10)
C12 0.1069(19) 0.0549(14) 0.0559(13) 0.0007(11) -0.0063(13) -0.0015(13)
C13 0.108(2) 0.0722(17) 0.0921(19) 0.0198(15) -0.0300(16) -0.0327(15)
C14 0.0751(14) 0.0696(15) 0.0669(14) 0.0028(12) -0.0021(12) -0.0146(12)
C15 0.0794(16) 0.0609(14) 0.0820(17) -0.0044(13) -0.0012(13) -0.0067(12)
C16 0.0922(18) 0.0748(17) 0.0835(18) 0.0074(14) -0.0071(15) 0.0008(14)
C17 0.114(2) 0.090(2) 0.097(2) 0.0074(17) -0.021(2) 0.0048(18)
C18 0.105(3) 0.114(3) 0.138(3) -0.004(2) -0.042(3) 0.013(2)
C19 0.090(2) 0.162(4) 0.153(4) -0.010(3) 0.000(3) 0.015(2)
C20 0.085(2) 0.135(3) 0.109(2) -0.011(2) 0.0004(19) 0.0004(19)

_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 C1 1.210(2) . ?
O2 C12 1.212(3) . ?
N1 C1 1.350(2) . ?
N1 C10 1.444(3) . ?
N1 C3 1.474(3) . ?
N2 N3 1.209(3) . ?
N2 C2 1.464(3) . ?
N3 N4 1.119(3) . ?
N5 C12 1.362(3) . ?
N5 C11 1.452(3) . ?
N5 C14 1.465(3) . ?
N6 N7 1.216(9) . ?
N6 C13 1.471(9) . ?
N7 N8 1.102(9) . ?
N6' N7' 1.211(15) . ?
N6' C13 1.530(14) . ?
N7' N8' 1.123(11) . ?
C1 C2 1.529(3) . ?
C2 C3 1.570(3) . ?
C3 C4 1.496(3) . ?
C4 C5 1.383(3) . ?
C4 C9 1.386(3) . ?
C5 C6 1.380(3) . ?
C6 C7 1.371(4) . ?
C7 C8 1.363(4) . ?
C8 C9 1.377(3) . ?
C10 C11 1.518(3) . ?
C12 C13 1.521(4) . ?
C13 C14 1.577(4) . ?
C14 C15 1.487(3) . ?
C15 C20 1.378(4) . ?
C15 C16 1.387(4) . ?
C16 C17 1.376(4) . ?
C17 C18 1.364(5) . ?
C18 C19 1.374(5) . ?
C19 C20 1.372(5) . ?

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 C10 130.54(16) . . ?
C1 N1 C3 95.98(16) . . ?
C10 N1 C3 132.31(15) . . ?
N3 N2 C2 117.66(18) . . ?
N4 N3 N2 170.9(3) . . ?
C12 N5 C11 130.5(2) . . ?
C12 N5 C14 96.18(19) . . ?
C11 N5 C14 131.88(18) . . ?
N7 N6 C13 107.2(8) . . ?
N8 N7 N6 169.8(17) . . ?
N7' N6' C13 112.2(18) . . ?
N8' N7' N6' 172.8(16) . . ?
O1 C1 N1 132.22(19) . . ?
O1 C1 C2 135.41(19) . . ?
N1 C1 C2 92.35(15) . . ?
N2 C2 C1 108.88(16) . . ?
N2 C2 C3 118.23(17) . . ?
C1 C2 C3 85.27(15) . . ?
N1 C3 C4 116.81(17) . . ?
N1 C3 C2 86.21(13) . . ?
C4 C3 C2 119.00(17) . . ?
C5 C4 C9 118.3(2) . . ?
C5 C4 C3 119.5(2) . . ?
C9 C4 C3 122.08(17) . . ?
C6 C5 C4 120.8(2) . . ?
C7 C6 C5 120.0(2) . . ?
C8 C7 C6 119.8(2) . . ?
C7 C8 C9 120.8(3) . . ?
C8 C9 C4 120.3(2) . . ?
N1 C10 C11 111.45(18) . . ?
N5 C11 C10 112.27(17) . . ?
O2 C12 N5 132.1(2) . . ?
O2 C12 C13 135.8(2) . . ?
N5 C12 C13 92.1(2) . . ?
N6 C13 C12 134.0(3) . . ?
N6 C13 N6' 37.8(5) . . ?
C12 C13 N6' 96.5(6) . . ?
N6 C13 C14 117.8(4) . . ?
C12 C13 C14 85.55(18) . . ?
N6' C13 C14 119.9(6) . . ?
N5 C14 C15 116.3(2) . . ?
N5 C14 C13 86.14(18) . . ?
C15 C14 C13 118.5(2) . . ?
C20 C15 C16 117.8(3) . . ?
C20 C15 C14 119.4(3) . . ?
C16 C15 C14 122.7(2) . . ?
C17 C16 C15 121.1(3) . . ?
C18 C17 C16 120.0(3) . . ?
C17 C18 C19 119.9(4) . . ?
C20 C19 C18 120.1(4) . . ?
C19 C20 C15 121.2(3) . . ?

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
C2 N2 N3 N4 172.9(18) . . . . ?
C13 N6 N7 N8 -164(6) . . . . ?
C13 N6' N7' N8' -129(24) . . . . ?
C10 N1 C1 O1 -6.6(4) . . . . ?
C3 N1 C1 O1 -175.1(2) . . . . ?
C10 N1 C1 C2 172.06(19) . . . . ?
C3 N1 C1 C2 3.51(16) . . . . ?
N3 N2 C2 C1 -160.77(19) . . . . ?
N3 N2 C2 C3 -65.9(3) . . . . ?
O1 C1 C2 N2 -66.5(3) . . . . ?
N1 C1 C2 N2 114.97(17) . . . . ?
O1 C1 C2 C3 175.3(2) . . . . ?
N1 C1 C2 C3 -3.29(15) . . . . ?
C1 N1 C3 C4 -124.15(19) . . . . ?
C10 N1 C3 C4 67.6(3) . . . . ?
C1 N1 C3 C2 -3.42(15) . . . . ?
C10 N1 C3 C2 -171.7(2) . . . . ?
N2 C2 C3 N1 -105.89(18) . . . . ?
C1 C2 C3 N1 3.02(14) . . . . ?
N2 C2 C3 C4 12.8(3) . . . . ?
C1 C2 C3 C4 121.71(18) . . . . ?
N1 C3 C4 C5 -152.5(2) . . . . ?
C2 C3 C4 C5 106.2(2) . . . . ?
N1 C3 C4 C9 30.9(3) . . . . ?
C2 C3 C4 C9 -70.3(3) . . . . ?
C9 C4 C5 C6 0.7(3) . . . . ?
C3 C4 C5 C6 -176.0(2) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C6 C7 C8 C9 0.3(5) . . . . ?
C7 C8 C9 C4 0.6(4) . . . . ?
C5 C4 C9 C8 -1.1(4) . . . . ?
C3 C4 C9 C8 175.5(2) . . . . ?
C1 N1 C10 C11 -91.5(2) . . . . ?
C3 N1 C10 C11 73.0(3) . . . . ?
C12 N5 C11 C10 -89.7(3) . . . . ?
C14 N5 C11 C10 73.1(3) . . . . ?
N1 C10 C11 N5 53.2(2) . . . . ?
C11 N5 C12 O2 -12.0(4) . . . . ?
C14 N5 C12 O2 -179.2(3) . . . . ?
C11 N5 C12 C13 165.8(2) . . . . ?
C14 N5 C12 C13 -1.44(19) . . . . ?
N7 N6 C13 C12 -32.3(13) . . . . ?
N7 N6 C13 N6' -23.3(8) . . . . ?
N7 N6 C13 C14 80.5(11) . . . . ?
O2 C12 C13 N6 -55.9(7) . . . . ?
N5 C12 C13 N6 126.5(5) . . . . ?
O2 C12 C13 N6' -61.4(7) . . . . ?
N5 C12 C13 N6' 120.9(6) . . . . ?
O2 C12 C13 C14 179.0(3) . . . . ?
N5 C12 C13 C14 1.34(18) . . . . ?
N7' N6' C13 N6 25.5(12) . . . . ?
N7' N6' C13 C12 -161.0(19) . . . . ?
N7' N6' C13 C14 -72(2) . . . . ?
C12 N5 C14 C15 -118.6(2) . . . . ?
C11 N5 C14 C15 74.5(3) . . . . ?
C12 N5 C14 C13 1.39(19) . . . . ?
C11 N5 C14 C13 -165.5(2) . . . . ?
N6 C13 C14 N5 -139.5(3) . . . . ?
C12 C13 C14 N5 -1.24(17) . . . . ?
N6' C13 C14 N5 -96.2(7) . . . . ?
N6 C13 C14 C15 -21.6(4) . . . . ?
C12 C13 C14 C15 116.7(2) . . . . ?
N6' C13 C14 C15 21.7(7) . . . . ?
N5 C14 C15 C20 -169.6(2) . . . . ?
C13 C14 C15 C20 89.9(3) . . . . ?
N5 C14 C15 C16 13.2(3) . . . . ?
C13 C14 C15 C16 -87.4(3) . . . . ?
C20 C15 C16 C17 1.0(4) . . . . ?
C14 C15 C16 C17 178.2(2) . . . . ?
C15 C16 C17 C18 -1.1(4) . . . . ?
C16 C17 C18 C19 0.5(5) . . . . ?
C17 C18 C19 C20 0.2(6) . . . . ?
C18 C19 C20 C15 -0.4(6) . . . . ?
C16 C15 C20 C19 -0.2(5) . . . . ?
C14 C15 C20 C19 -177.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.030

# Attachment 'NSV-4.cif'

data_4
_database_code_depnum_ccdc_archive 'CCDC 690112'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1-[3'-azido-4'-phenylazetidine-2'-one-1'-yl]-2-
[3"-azido-4"-phenylazetidine-2"-one-1"-yl]ethane
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 N8 O2'
_chemical_formula_sum            'C20 H18 N8 O2'
_chemical_formula_weight         402.42

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'
O O 0.0106 0.0060 '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   'P 21/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                   13.196(8)
_cell_length_b                   5.751(4)
_cell_length_c                   13.632(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.453(9)
_cell_angle_gamma                90.00
_cell_volume                     975.4(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3664
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      27.77

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless'
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9296
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_process_details   'bruker sadabs'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(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_device       'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8813
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1715
_reflns_number_gt                1538
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'

_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^)+(0.0419P)^2^+0.2023P] 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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1715
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
O1 O 0.49932(10) 0.9761(2) 0.32493(10) 0.0765(4) Uani 1 1 d . . .
N1 N 0.41808(8) 0.6790(2) 0.38820(9) 0.0471(3) Uani 1 1 d . . .
N2 N 0.24536(10) 0.9250(2) 0.19948(10) 0.0615(4) Uani 1 1 d . . .
N3 N 0.25915(9) 1.0675(2) 0.13832(9) 0.0516(3) Uani 1 1 d . . .
N4 N 0.26118(13) 1.2082(3) 0.08218(12) 0.0771(5) Uani 1 1 d . . .
C1 C 0.43215(11) 0.8306(2) 0.31892(12) 0.0495(4) Uani 1 1 d . . .
C2 C 0.32989(11) 0.7501(3) 0.23467(10) 0.0466(3) Uani 1 1 d . . .
H2 H 0.3438 0.6689 0.1772 0.056 Uiso 1 1 calc R . .
C3 C 0.31597(10) 0.5826(2) 0.31849(10) 0.0433(3) Uani 1 1 d . . .
H3 H 0.3242 0.4200 0.3010 0.052 Uiso 1 1 calc R . .
C4 C 0.22010(10) 0.6137(2) 0.35299(10) 0.0417(3) Uani 1 1 d . . .
C5 C 0.20996(12) 0.8024(3) 0.41183(11) 0.0508(4) Uani 1 1 d . . .
H5 H 0.2644 0.9130 0.4325 0.061 Uiso 1 1 calc R . .
C6 C 0.11951(13) 0.8274(3) 0.44000(12) 0.0591(4) Uani 1 1 d . . .
H6 H 0.1135 0.9536 0.4803 0.071 Uiso 1 1 calc R . .
C7 C 0.03819(12) 0.6664(3) 0.40870(12) 0.0598(4) Uani 1 1 d . . .
H7 H -0.0229 0.6841 0.4276 0.072 Uiso 1 1 calc R . .
C8 C 0.04696(12) 0.4803(3) 0.34987(12) 0.0602(4) Uani 1 1 d . . .
H8 H -0.0085 0.3721 0.3282 0.072 Uiso 1 1 calc R . .
C9 C 0.13797(11) 0.4526(3) 0.32263(11) 0.0510(4) Uani 1 1 d . . .
H9 H 0.1441 0.3242 0.2835 0.061 Uiso 1 1 calc R . .
C10 C 0.48117(12) 0.6237(3) 0.49459(12) 0.0541(4) Uani 1 1 d . . .
H10A H 0.4381 0.6500 0.5390 0.065 Uiso 1 1 calc R . .
H10B H 0.5430 0.7264 0.5175 0.065 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
O1 0.0651(7) 0.0689(7) 0.0970(9) 0.0068(7) 0.0289(6) -0.0213(6)
N1 0.0370(6) 0.0505(7) 0.0503(6) 0.0034(5) 0.0099(5) -0.0024(5)
N2 0.0550(7) 0.0770(9) 0.0611(8) 0.0238(7) 0.0307(6) 0.0229(7)
N3 0.0487(7) 0.0583(8) 0.0454(7) 0.0025(6) 0.0127(5) 0.0072(6)
N4 0.0852(11) 0.0715(10) 0.0700(9) 0.0206(8) 0.0196(8) 0.0050(8)
C1 0.0433(8) 0.0472(8) 0.0626(9) 0.0028(7) 0.0236(7) 0.0021(6)
C2 0.0425(7) 0.0540(8) 0.0481(7) 0.0019(6) 0.0217(6) 0.0078(6)
C3 0.0389(7) 0.0428(7) 0.0474(7) -0.0028(6) 0.0134(6) -0.0010(5)
C4 0.0399(7) 0.0442(7) 0.0397(7) 0.0040(5) 0.0115(5) -0.0018(6)
C5 0.0493(8) 0.0487(8) 0.0571(8) -0.0052(6) 0.0212(7) -0.0070(6)
C6 0.0619(10) 0.0633(10) 0.0597(9) -0.0035(7) 0.0302(8) 0.0052(8)
C7 0.0464(8) 0.0790(11) 0.0605(9) 0.0134(8) 0.0264(7) 0.0038(8)
C8 0.0450(8) 0.0695(10) 0.0651(9) 0.0050(8) 0.0170(7) -0.0134(7)
C9 0.0474(8) 0.0518(8) 0.0513(8) -0.0030(6) 0.0130(6) -0.0079(6)
C10 0.0471(8) 0.0584(9) 0.0518(8) -0.0030(7) 0.0096(6) 0.0035(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 C1 1.2017(18) . ?
N1 C1 1.3427(18) . ?
N1 C10 1.447(2) . ?
N1 C3 1.4740(18) . ?
N2 N3 1.2252(18) . ?
N2 C2 1.4593(19) . ?
N3 N4 1.1200(18) . ?
C1 C2 1.524(2) . ?
C2 C3 1.551(2) . ?
C3 C4 1.4999(19) . ?
C4 C9 1.380(2) . ?
C4 C5 1.382(2) . ?
C5 C6 1.378(2) . ?
C6 C7 1.373(2) . ?
C7 C8 1.365(2) . ?
C8 C9 1.379(2) . ?
C10 C10 1.499(3) 3_666 ?

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 C10 132.80(12) . . ?
C1 N1 C3 95.83(11) . . ?
C10 N1 C3 131.37(12) . . ?
N3 N2 C2 114.47(12) . . ?
N4 N3 N2 172.27(15) . . ?
O1 C1 N1 132.51(15) . . ?
O1 C1 C2 135.30(14) . . ?
N1 C1 C2 92.17(11) . . ?
N2 C2 C1 115.25(13) . . ?
N2 C2 C3 113.88(11) . . ?
C1 C2 C3 85.74(11) . . ?
N1 C3 C4 116.00(11) . . ?
N1 C3 C2 86.23(10) . . ?
C4 C3 C2 118.43(11) . . ?
C9 C4 C5 118.88(13) . . ?
C9 C4 C3 119.07(13) . . ?
C5 C4 C3 122.02(12) . . ?
C6 C5 C4 120.25(14) . . ?
C7 C6 C5 120.21(15) . . ?
C8 C7 C6 120.05(14) . . ?
C7 C8 C9 120.03(14) . . ?
C8 C9 C4 120.58(15) . . ?
N1 C10 C10 111.63(16) . 3_666 ?

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
C2 N2 N3 N4 179(100) . . . . ?
C10 N1 C1 O1 -4.0(3) . . . . ?
C3 N1 C1 O1 176.84(17) . . . . ?
C10 N1 C1 C2 177.78(14) . . . . ?
C3 N1 C1 C2 -1.39(10) . . . . ?
N3 N2 C2 C1 78.66(17) . . . . ?
N3 N2 C2 C3 175.50(12) . . . . ?
O1 C1 C2 N2 -62.4(2) . . . . ?
N1 C1 C2 N2 115.76(12) . . . . ?
O1 C1 C2 C3 -176.82(18) . . . . ?
N1 C1 C2 C3 1.32(10) . . . . ?
C1 N1 C3 C4 -118.55(13) . . . . ?
C10 N1 C3 C4 62.26(19) . . . . ?
C1 N1 C3 C2 1.37(10) . . . . ?
C10 N1 C3 C2 -177.83(14) . . . . ?
N2 C2 C3 N1 -116.98(13) . . . . ?
C1 C2 C3 N1 -1.20(9) . . . . ?
N2 C2 C3 C4 0.67(18) . . . . ?
C1 C2 C3 C4 116.44(13) . . . . ?
N1 C3 C4 C9 -151.51(12) . . . . ?
C2 C3 C4 C9 108.06(15) . . . . ?
N1 C3 C4 C5 30.37(18) . . . . ?
C2 C3 C4 C5 -70.06(17) . . . . ?
C9 C4 C5 C6 0.4(2) . . . . ?
C3 C4 C5 C6 178.54(13) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C5 C6 C7 C8 0.3(2) . . . . ?
C6 C7 C8 C9 0.6(2) . . . . ?
C7 C8 C9 C4 -1.0(2) . . . . ?
C5 C4 C9 C8 0.5(2) . . . . ?
C3 C4 C9 C8 -177.69(13) . . . . ?
C1 N1 C10 C10 -117.63(19) . . . 3_666 ?
C3 N1 C10 C10 61.3(2) . . . 3_666 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.030