# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       iva108@googlemail.com
_publ_contact_author_name        'Viktor Iaroshenko'
loop_
_publ_author_name
'Viktor O. Iaroshenko'
'Satenik Mkrtchyan'
'Ashot Gevorgyan'
'Mariia Miliutina'
'Alexander Villinger'
'Vyacheslav Ya. Sosnovskikh'
'Peter Langer'

data_av_ag145
_database_code_depnum_ccdc_archive 'CCDC 835825'
#TrackingRef 'av_ag145.cif'

_audit_author_name               'Villinger, A.'
_audit_creation_method           SHELXL-97

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

# CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 N3 O2'
_chemical_formula_sum            'C18 H13 N3 O2'
_chemical_formula_weight         303.31

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'

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

# CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19

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

_cell_length_a                   6.1634(6)
_cell_length_b                   11.2748(10)
_cell_length_c                   19.9532(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1386.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1942
_cell_measurement_theta_min      5.452
_cell_measurement_theta_max      43.105

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9482
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13573
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_sigmaI/netI    0.0625
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3171
_reflns_number_gt                2330
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker Apex v2.0-2'
_computing_cell_refinement       'Bruker Apex v2.0-2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

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

# REFINEMENT DATA

_refine_special_details          
;
All H atoms (with exception of H1 and H2) were positioned geometrically and
refined using a riding model , with C---H = 0.98 (methyl groups), 0.99\%A
(methylene groups), 1.00\%A (methine groups) or 0.95 \%A (aryl CH) and
with <i>U</i>~iso~(H) = 1.5 times <i>U</i>~eq~(C) (methyl groups) or with
<i>U</i>~iso~(H) = 1.2 times <i>U</i>~eq~(C) (methylene groups, aryl CH,
methine groups). Torsion angles of all methyl groups were allowed to refine.

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^ > 2\s(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^)+(0.0420P)^2^+0.0000P] 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   0.0(15)
_refine_ls_number_reflns         3171
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0303(3) 0.72573(14) 0.71370(7) 0.0251(4) Uani 1 1 d . . .
N2 N 0.1948(3) 0.80685(15) 0.73201(8) 0.0263(4) Uani 1 1 d . . .
N3 N 0.4941(3) 0.79504(14) 0.80709(8) 0.0250(4) Uani 1 1 d . . .
O1 O -0.0452(3) 0.52658(12) 0.72914(7) 0.0328(4) Uani 1 1 d . . .
O2 O 0.6630(3) 0.97560(13) 0.86715(8) 0.0358(4) Uani 1 1 d . . .
C1 C 0.0711(4) 0.61319(17) 0.73921(9) 0.0250(5) Uani 1 1 d . . .
C2 C 0.2695(4) 0.62633(17) 0.77710(9) 0.0240(5) Uani 1 1 d . . .
C3 C 0.5748(4) 0.59765(18) 0.84690(9) 0.0282(5) Uani 1 1 d . . .
H3 H 0.6673 0.5474 0.8723 0.034 Uiso 1 1 calc R . .
C4 C 0.6185(3) 0.72049(18) 0.84380(9) 0.0245(5) Uani 1 1 d . . .
C5 C 0.3999(4) 0.54989(18) 0.81359(10) 0.0285(5) Uani 1 1 d . . .
H5 H 0.3697 0.4673 0.8155 0.034 Uiso 1 1 calc R . .
C6 C 0.3281(3) 0.74515(17) 0.77450(9) 0.0234(5) Uani 1 1 d . . .
C7 C -0.1069(3) 0.75547(17) 0.65951(9) 0.0244(5) Uani 1 1 d . . .
C8 C -0.3062(4) 0.69978(18) 0.65295(10) 0.0289(5) Uani 1 1 d . . .
H8 H -0.3504 0.6416 0.6845 0.035 Uiso 1 1 calc R . .
C9 C -0.4401(4) 0.7298(2) 0.59995(10) 0.0351(5) Uani 1 1 d . . .
H9 H -0.5762 0.6912 0.5949 0.042 Uiso 1 1 calc R . .
C10 C -0.3775(4) 0.8154(2) 0.55430(11) 0.0373(6) Uani 1 1 d . . .
H10 H -0.4715 0.8366 0.5185 0.045 Uiso 1 1 calc R . .
C11 C -0.1782(4) 0.8701(2) 0.56073(10) 0.0364(6) Uani 1 1 d . . .
H11 H -0.1347 0.9284 0.5291 0.044 Uiso 1 1 calc R . .
C12 C -0.0417(4) 0.84046(18) 0.61301(9) 0.0290(5) Uani 1 1 d . . .
H12 H 0.0958 0.8778 0.6172 0.035 Uiso 1 1 calc R . .
C13 C 0.8009(3) 0.77455(18) 0.88050(9) 0.0248(5) Uani 1 1 d . . .
C14 C 0.8152(4) 0.89838(19) 0.88980(10) 0.0279(5) Uani 1 1 d . . .
C15 C 0.9902(4) 0.9461(2) 0.92464(10) 0.0342(6) Uani 1 1 d . . .
H15 H 0.9992 1.0295 0.9307 0.041 Uiso 1 1 calc R . .
C16 C 1.1496(4) 0.8749(2) 0.95040(10) 0.0372(6) Uani 1 1 d . . .
H16 H 1.2683 0.9092 0.9738 0.045 Uiso 1 1 calc R . .
C17 C 1.1386(4) 0.7530(2) 0.94242(10) 0.0333(5) Uani 1 1 d . . .
H17 H 1.2476 0.7032 0.9609 0.040 Uiso 1 1 calc R . .
C18 C 0.9681(4) 0.7050(2) 0.90746(9) 0.0300(5) Uani 1 1 d . . .
H18 H 0.9631 0.6215 0.9013 0.036 Uiso 1 1 calc R . .
H1 H 0.144(3) 0.8780(18) 0.7451(9) 0.026(6) Uiso 1 1 d . . .
H2 H 0.565(5) 0.926(3) 0.8352(14) 0.095(11) Uiso 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
N1 0.0264(10) 0.0169(8) 0.0320(9) -0.0002(7) -0.0018(8) -0.0023(8)
N2 0.0300(11) 0.0158(9) 0.0331(9) -0.0034(8) -0.0028(9) -0.0002(8)
N3 0.0265(11) 0.0205(8) 0.0280(8) -0.0002(7) 0.0004(8) 0.0013(8)
O1 0.0338(9) 0.0206(7) 0.0441(8) 0.0028(6) 0.0000(8) -0.0064(7)
O2 0.0369(10) 0.0240(8) 0.0465(9) -0.0026(7) -0.0069(8) 0.0033(7)
C1 0.0291(13) 0.0205(10) 0.0253(10) -0.0013(8) 0.0062(10) 0.0012(10)
C2 0.0287(13) 0.0181(10) 0.0254(9) -0.0015(8) 0.0040(9) 0.0003(9)
C3 0.0292(13) 0.0220(10) 0.0335(11) 0.0024(9) 0.0001(10) 0.0061(10)
C4 0.0263(12) 0.0237(10) 0.0236(10) -0.0002(9) 0.0064(9) 0.0040(9)
C5 0.0329(14) 0.0175(10) 0.0352(11) 0.0043(9) 0.0049(11) 0.0019(10)
C6 0.0269(12) 0.0195(10) 0.0238(9) 0.0005(8) 0.0042(9) 0.0033(9)
C7 0.0280(12) 0.0202(10) 0.0250(10) -0.0036(8) 0.0010(9) 0.0027(9)
C8 0.0303(13) 0.0244(11) 0.0321(11) 0.0015(9) 0.0028(10) -0.0010(10)
C9 0.0323(14) 0.0317(12) 0.0412(12) 0.0003(10) -0.0045(11) -0.0049(11)
C10 0.0438(16) 0.0329(13) 0.0352(12) 0.0009(11) -0.0119(12) -0.0011(11)
C11 0.0506(17) 0.0295(12) 0.0290(11) 0.0047(10) -0.0018(12) -0.0015(12)
C12 0.0289(13) 0.0251(11) 0.0329(11) 0.0000(9) 0.0019(10) -0.0036(10)
C13 0.0261(12) 0.0264(11) 0.0220(9) -0.0001(8) 0.0043(9) 0.0018(10)
C14 0.0293(13) 0.0276(11) 0.0270(10) 0.0017(9) 0.0014(10) 0.0021(11)
C15 0.0404(16) 0.0312(12) 0.0309(11) -0.0041(9) -0.0031(11) -0.0064(12)
C16 0.0348(15) 0.0507(15) 0.0262(11) 0.0025(11) -0.0053(11) -0.0056(13)
C17 0.0305(14) 0.0402(13) 0.0292(10) 0.0042(11) 0.0009(10) 0.0061(12)
C18 0.0324(14) 0.0313(12) 0.0262(10) 0.0020(9) 0.0038(10) 0.0036(11)

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

# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.390(2) . ?
N1 C7 1.413(2) . ?
N1 N2 1.413(2) . ?
N2 C6 1.370(2) . ?
N2 H1 0.90(2) . ?
N3 C6 1.337(3) . ?
N3 C4 1.353(2) . ?
O1 C1 1.228(2) . ?
O2 C14 1.357(2) . ?
O2 H2 1.04(3) . ?
C1 C2 1.445(3) . ?
C2 C5 1.385(3) . ?
C2 C6 1.388(3) . ?
C3 C5 1.376(3) . ?
C3 C4 1.412(3) . ?
C3 H3 0.9500 . ?
C4 C13 1.474(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.386(3) . ?
C7 C12 1.393(3) . ?
C8 C9 1.383(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.402(3) . ?
C13 C14 1.411(3) . ?
C14 C15 1.391(3) . ?
C15 C16 1.369(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.372(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

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 C7 127.22(17) . . ?
C1 N1 N2 111.50(16) . . ?
C7 N1 N2 118.27(16) . . ?
C6 N2 N1 105.15(16) . . ?
C6 N2 H1 118.8(12) . . ?
N1 N2 H1 113.7(14) . . ?
C6 N3 C4 115.84(17) . . ?
C14 O2 H2 105.1(18) . . ?
O1 C1 N1 124.11(19) . . ?
O1 C1 C2 131.37(19) . . ?
N1 C1 C2 104.52(17) . . ?
C5 C2 C6 118.0(2) . . ?
C5 C2 C1 134.60(19) . . ?
C6 C2 C1 107.42(18) . . ?
C5 C3 C4 120.79(19) . . ?
C5 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
N3 C4 C3 121.66(19) . . ?
N3 C4 C13 116.38(18) . . ?
C3 C4 C13 121.96(18) . . ?
C3 C5 C2 117.71(18) . . ?
C3 C5 H5 121.1 . . ?
C2 C5 H5 121.1 . . ?
N3 C6 N2 123.11(18) . . ?
N3 C6 C2 125.95(19) . . ?
N2 C6 C2 110.93(18) . . ?
C8 C7 C12 120.30(19) . . ?
C8 C7 N1 119.69(18) . . ?
C12 C7 N1 120.0(2) . . ?
C9 C8 C7 119.4(2) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C18 C13 C14 117.2(2) . . ?
C18 C13 C4 121.34(19) . . ?
C14 C13 C4 121.48(19) . . ?
O2 C14 C15 117.0(2) . . ?
O2 C14 C13 123.21(19) . . ?
C15 C14 C13 119.8(2) . . ?
C16 C15 C14 121.2(2) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.1(2) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C13 122.5(2) . . ?
C17 C18 H18 118.7 . . ?
C13 C18 H18 118.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C6 -5.4(2) . . . . ?
C7 N1 N2 C6 -167.18(16) . . . . ?
C7 N1 C1 O1 -18.6(3) . . . . ?
N2 N1 C1 O1 -178.36(18) . . . . ?
C7 N1 C1 C2 161.41(18) . . . . ?
N2 N1 C1 C2 1.6(2) . . . . ?
O1 C1 C2 C5 1.4(4) . . . . ?
N1 C1 C2 C5 -178.6(2) . . . . ?
O1 C1 C2 C6 -177.3(2) . . . . ?
N1 C1 C2 C6 2.8(2) . . . . ?
C6 N3 C4 C3 0.3(3) . . . . ?
C6 N3 C4 C13 -179.43(16) . . . . ?
C5 C3 C4 N3 -1.5(3) . . . . ?
C5 C3 C4 C13 178.23(18) . . . . ?
C4 C3 C5 C2 0.1(3) . . . . ?
C6 C2 C5 C3 2.3(3) . . . . ?
C1 C2 C5 C3 -176.3(2) . . . . ?
C4 N3 C6 N2 -175.91(18) . . . . ?
C4 N3 C6 C2 2.4(3) . . . . ?
N1 N2 C6 N3 -174.30(17) . . . . ?
N1 N2 C6 C2 7.2(2) . . . . ?
C5 C2 C6 N3 -3.8(3) . . . . ?
C1 C2 C6 N3 175.15(17) . . . . ?
C5 C2 C6 N2 174.70(18) . . . . ?
C1 C2 C6 N2 -6.4(2) . . . . ?
C1 N1 C7 C8 41.4(3) . . . . ?
N2 N1 C7 C8 -159.97(17) . . . . ?
C1 N1 C7 C12 -138.6(2) . . . . ?
N2 N1 C7 C12 20.0(3) . . . . ?
C12 C7 C8 C9 -0.3(3) . . . . ?
N1 C7 C8 C9 179.70(17) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C8 C9 C10 C11 1.2(3) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C10 C11 C12 C7 -0.4(3) . . . . ?
C8 C7 C12 C11 0.9(3) . . . . ?
N1 C7 C12 C11 -179.11(18) . . . . ?
N3 C4 C13 C18 -165.38(17) . . . . ?
C3 C4 C13 C18 14.9(3) . . . . ?
N3 C4 C13 C14 14.4(3) . . . . ?
C3 C4 C13 C14 -165.34(18) . . . . ?
C18 C13 C14 O2 -179.00(18) . . . . ?
C4 C13 C14 O2 1.2(3) . . . . ?
C18 C13 C14 C15 -0.1(3) . . . . ?
C4 C13 C14 C15 -179.89(17) . . . . ?
O2 C14 C15 C16 178.82(19) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C16 C17 C18 C13 -1.4(3) . . . . ?
C14 C13 C18 C17 0.9(3) . . . . ?
C4 C13 C18 C17 -179.33(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.045
# Attachment 'is_ag124.cif'

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

data_is_ag124
_database_code_depnum_ccdc_archive 'CCDC 835826'
#TrackingRef 'is_ag124.cif'

_audit_author_name               'Villinger, A.'
_audit_creation_method           SHELXL-97

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

# CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 Cl N3 O2'
_chemical_formula_sum            'C18 H12 Cl N3 O2'
_chemical_formula_weight         337.76

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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                   13.5897(4)
_cell_length_b                   11.4742(3)
_cell_length_c                   10.2062(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.969(2)
_cell_angle_gamma                90.00
_cell_volume                     1486.07(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6354
_cell_measurement_theta_min      5.557
_cell_measurement_theta_max      64.675

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9151
_exptl_absorpt_correction_T_max  0.9627
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17175
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         29.00
_reflns_number_total             3944
_reflns_number_gt                3251
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker Apex v2.0-2'
_computing_cell_refinement       'Bruker Apex v2.0-2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

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

# REFINEMENT DATA

_refine_special_details          
;
All H atoms (with exception of H1/H4) were positioned geometrically and
refined using a riding model , with C---H = 0.98 (methyl groups), 0.99\%A
(methylene groups), 1.00\%A (methine groups) or 0.95 \%A (aryl CH) and
with <i>U</i>~iso~(H) = 1.5 times <i>U</i>~eq~(C) (methyl groups) or with
<i>U</i>~iso~(H) = 1.2 times <i>U</i>~eq~(C) (methylene groups, aryl CH,
methine groups). Torsion angles of all methyl groups were allowed to refine.

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^ > 2\s(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^)+(0.0528P)^2^+0.2511P] 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         3944
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
C18 C 0.70036(9) 0.82505(10) 0.65862(13) 0.0241(2) Uani 1 1 d . . .
Cl1 Cl 0.50053(3) 0.59588(3) 0.30184(3) 0.03449(10) Uani 1 1 d . . .
N1 N 0.84092(8) 0.71791(8) 0.90421(10) 0.0230(2) Uani 1 1 d . . .
N2 N 0.98232(8) 0.72474(9) 1.12554(11) 0.0254(2) Uani 1 1 d . . .
N3 N 1.02501(8) 0.64347(9) 1.23512(11) 0.0235(2) Uani 1 1 d . . .
O1 O 1.01353(7) 0.44367(8) 1.26395(10) 0.0331(2) Uani 1 1 d . . .
O2 O 0.75922(8) 0.89951(8) 0.75837(10) 0.0316(2) Uani 1 1 d . . .
H1 H 0.9735(14) 0.7985(18) 1.1539(19) 0.056(5) Uiso 1 1 d . . .
H4 H 0.8005(15) 0.8583(18) 0.830(2) 0.061(6) Uiso 1 1 d . . .
C1 C 0.77425(9) 0.64655(10) 0.80748(12) 0.0211(2) Uani 1 1 d . . .
C2 C 0.77097(9) 0.52483(10) 0.83083(13) 0.0234(2) Uani 1 1 d . . .
H2 H 0.7239 0.4768 0.7601 0.028 Uiso 1 1 calc R . .
C3 C 0.83545(9) 0.47571(10) 0.95523(13) 0.0236(2) Uani 1 1 d . . .
H3 H 0.8335 0.3945 0.9721 0.028 Uiso 1 1 calc R . .
C4 C 0.90358(9) 0.54959(10) 1.05538(12) 0.0219(2) Uani 1 1 d . . .
C5 C 0.98283(9) 0.53276(10) 1.19386(13) 0.0229(2) Uani 1 1 d . . .
C6 C 0.90426(9) 0.66732(10) 1.02216(12) 0.0217(2) Uani 1 1 d . . .
C7 C 1.12721(9) 0.66660(10) 1.33500(12) 0.0222(2) Uani 1 1 d . . .
C8 C 1.16468(10) 0.60229(11) 1.45919(13) 0.0269(3) Uani 1 1 d . . .
H8 H 1.1204 0.5477 1.4814 0.032 Uiso 1 1 calc R . .
C9 C 1.26818(10) 0.61948(12) 1.55011(13) 0.0301(3) Uani 1 1 d . . .
H9 H 1.2949 0.5752 1.6341 0.036 Uiso 1 1 calc R . .
C10 C 1.33255(10) 0.70018(12) 1.51966(14) 0.0306(3) Uani 1 1 d . . .
H10 H 1.4034 0.7101 1.5814 0.037 Uiso 1 1 calc R . .
C11 C 1.29304(10) 0.76651(11) 1.39832(14) 0.0291(3) Uani 1 1 d . . .
H11 H 1.3366 0.8234 1.3786 0.035 Uiso 1 1 calc R . .
C12 C 1.19053(10) 0.75060(10) 1.30548(13) 0.0255(2) Uani 1 1 d . . .
H12 H 1.1638 0.7964 1.2227 0.031 Uiso 1 1 calc R . .
C13 C 0.70489(9) 0.70221(10) 0.67582(12) 0.0219(2) Uani 1 1 d . . .
C14 C 0.64138(9) 0.63393(11) 0.56284(13) 0.0249(2) Uani 1 1 d . . .
H14 H 0.6431 0.5514 0.5714 0.030 Uiso 1 1 calc R . .
C15 C 0.57656(9) 0.68477(11) 0.43972(13) 0.0257(2) Uani 1 1 d . . .
C16 C 0.57072(10) 0.80536(11) 0.42395(13) 0.0283(3) Uani 1 1 d . . .
H16 H 0.5253 0.8397 0.3392 0.034 Uiso 1 1 calc R . .
C17 C 0.63204(10) 0.87412(11) 0.53355(14) 0.0283(3) Uani 1 1 d . . .
H17 H 0.6279 0.9565 0.5240 0.034 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
C18 0.0250(6) 0.0225(5) 0.0258(6) -0.0006(5) 0.0105(5) 0.0001(4)
Cl1 0.03052(17) 0.03833(19) 0.02662(17) -0.00273(13) 0.00047(13) -0.00460(12)
N1 0.0233(5) 0.0191(4) 0.0239(5) -0.0008(4) 0.0052(4) 0.0002(4)
N2 0.0290(5) 0.0163(4) 0.0247(5) 0.0005(4) 0.0020(4) 0.0007(4)
N3 0.0248(5) 0.0186(5) 0.0230(5) 0.0019(4) 0.0034(4) 0.0005(4)
O1 0.0336(5) 0.0218(4) 0.0359(5) 0.0081(4) 0.0025(4) -0.0031(3)
O2 0.0399(5) 0.0212(4) 0.0281(5) -0.0013(4) 0.0054(4) -0.0020(4)
C1 0.0197(5) 0.0213(5) 0.0227(5) -0.0016(4) 0.0080(4) 0.0004(4)
C2 0.0221(5) 0.0206(5) 0.0265(6) -0.0031(5) 0.0076(5) -0.0031(4)
C3 0.0231(5) 0.0183(5) 0.0287(6) -0.0009(5) 0.0085(5) -0.0021(4)
C4 0.0214(5) 0.0187(5) 0.0259(6) 0.0009(4) 0.0087(5) 0.0007(4)
C5 0.0221(5) 0.0195(5) 0.0263(6) 0.0008(4) 0.0077(5) -0.0016(4)
C6 0.0210(5) 0.0187(5) 0.0245(6) -0.0020(4) 0.0069(5) 0.0002(4)
C7 0.0233(5) 0.0200(5) 0.0213(5) -0.0037(4) 0.0055(4) 0.0012(4)
C8 0.0313(6) 0.0257(6) 0.0223(6) -0.0003(5) 0.0079(5) -0.0004(5)
C9 0.0344(7) 0.0301(6) 0.0212(6) -0.0015(5) 0.0044(5) 0.0047(5)
C10 0.0260(6) 0.0343(7) 0.0255(6) -0.0054(5) 0.0020(5) 0.0027(5)
C11 0.0273(6) 0.0295(6) 0.0294(6) -0.0039(5) 0.0087(5) -0.0038(5)
C12 0.0274(6) 0.0242(6) 0.0235(6) 0.0000(5) 0.0072(5) 0.0006(4)
C13 0.0211(5) 0.0225(5) 0.0228(6) 0.0002(4) 0.0086(5) 0.0010(4)
C14 0.0232(6) 0.0241(6) 0.0260(6) -0.0012(5) 0.0071(5) -0.0005(4)
C15 0.0218(5) 0.0305(6) 0.0236(6) -0.0020(5) 0.0067(5) -0.0024(5)
C16 0.0264(6) 0.0312(6) 0.0261(6) 0.0056(5) 0.0082(5) 0.0020(5)
C17 0.0319(6) 0.0239(6) 0.0292(6) 0.0040(5) 0.0111(5) 0.0015(5)

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

# MOLECULAR GEOMETRY

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
C18 O2 1.3504(14) . ?
C18 C17 1.4000(17) . ?
C18 C13 1.4189(16) . ?
Cl1 C15 1.7457(13) . ?
N1 C6 1.3362(15) . ?
N1 C1 1.3512(15) . ?
N2 C6 1.3681(15) . ?
N2 N3 1.4115(14) . ?
N2 H1 0.92(2) . ?
N3 C5 1.3953(15) . ?
N3 C7 1.4231(15) . ?
O1 C5 1.2317(15) . ?
O2 H4 0.88(2) . ?
C1 C2 1.4202(16) . ?
C1 C13 1.4817(16) . ?
C2 C3 1.3789(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3941(16) . ?
C3 H3 0.9500 . ?
C4 C6 1.3935(15) . ?
C4 C5 1.4509(17) . ?
C7 C12 1.3950(16) . ?
C7 C8 1.3958(16) . ?
C8 C9 1.3944(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.3835(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.3875(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3883(17) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.4057(16) . ?
C14 C15 1.3794(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3920(18) . ?
C16 C17 1.3788(18) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

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
O2 C18 C17 116.97(11) . . ?
O2 C18 C13 123.19(11) . . ?
C17 C18 C13 119.84(11) . . ?
C6 N1 C1 116.25(10) . . ?
C6 N2 N3 106.16(9) . . ?
C6 N2 H1 122.4(12) . . ?
N3 N2 H1 115.0(12) . . ?
C5 N3 N2 110.75(9) . . ?
C5 N3 C7 125.18(10) . . ?
N2 N3 C7 117.61(9) . . ?
C18 O2 H4 108.3(13) . . ?
N1 C1 C2 121.77(11) . . ?
N1 C1 C13 116.36(10) . . ?
C2 C1 C13 121.88(10) . . ?
C3 C2 C1 120.58(11) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 117.58(10) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
C6 C4 C3 118.13(11) . . ?
C6 C4 C5 107.39(10) . . ?
C3 C4 C5 134.42(11) . . ?
O1 C5 N3 124.27(11) . . ?
O1 C5 C4 130.94(11) . . ?
N3 C5 C4 104.73(10) . . ?
N1 C6 N2 123.87(10) . . ?
N1 C6 C4 125.60(10) . . ?
N2 C6 C4 110.48(10) . . ?
C12 C7 C8 120.57(11) . . ?
C12 C7 N3 119.56(11) . . ?
C8 C7 N3 119.82(10) . . ?
C9 C8 C7 118.88(12) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C10 C9 C8 120.90(12) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.59(12) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.69(12) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 119.30(11) . . ?
C11 C12 H12 120.4 . . ?
C7 C12 H12 120.4 . . ?
C14 C13 C18 117.73(11) . . ?
C14 C13 C1 120.55(10) . . ?
C18 C13 C1 121.72(10) . . ?
C15 C14 C13 121.06(11) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 121.14(11) . . ?
C14 C15 Cl1 119.21(10) . . ?
C16 C15 Cl1 119.65(10) . . ?
C17 C16 C15 118.82(11) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 121.38(11) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?

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
C6 N2 N3 C5 7.10(13) . . . . ?
C6 N2 N3 C7 160.42(10) . . . . ?
C6 N1 C1 C2 0.73(15) . . . . ?
C6 N1 C1 C13 -179.24(9) . . . . ?
N1 C1 C2 C3 0.94(17) . . . . ?
C13 C1 C2 C3 -179.09(10) . . . . ?
C1 C2 C3 C4 -0.40(16) . . . . ?
C2 C3 C4 C6 -1.69(16) . . . . ?
C2 C3 C4 C5 -178.60(11) . . . . ?
N2 N3 C5 O1 172.78(11) . . . . ?
C7 N3 C5 O1 21.91(19) . . . . ?
N2 N3 C5 C4 -4.82(12) . . . . ?
C7 N3 C5 C4 -155.68(11) . . . . ?
C6 C4 C5 O1 -176.61(13) . . . . ?
C3 C4 C5 O1 0.5(2) . . . . ?
C6 C4 C5 N3 0.76(12) . . . . ?
C3 C4 C5 N3 177.90(12) . . . . ?
C1 N1 C6 N2 174.28(10) . . . . ?
C1 N1 C6 C4 -3.10(16) . . . . ?
N3 N2 C6 N1 175.75(10) . . . . ?
N3 N2 C6 C4 -6.53(13) . . . . ?
C3 C4 C6 N1 3.66(17) . . . . ?
C5 C4 C6 N1 -178.65(10) . . . . ?
C3 C4 C6 N2 -174.01(10) . . . . ?
C5 C4 C6 N2 3.68(13) . . . . ?
C5 N3 C7 C12 134.49(12) . . . . ?
N2 N3 C7 C12 -14.60(16) . . . . ?
C5 N3 C7 C8 -43.22(17) . . . . ?
N2 N3 C7 C8 167.70(10) . . . . ?
C12 C7 C8 C9 -3.03(17) . . . . ?
N3 C7 C8 C9 174.65(11) . . . . ?
C7 C8 C9 C10 1.12(19) . . . . ?
C8 C9 C10 C11 1.21(19) . . . . ?
C9 C10 C11 C12 -1.67(19) . . . . ?
C10 C11 C12 C7 -0.22(18) . . . . ?
C8 C7 C12 C11 2.60(17) . . . . ?
N3 C7 C12 C11 -175.09(11) . . . . ?
O2 C18 C13 C14 -178.56(10) . . . . ?
C17 C18 C13 C14 1.69(16) . . . . ?
O2 C18 C13 C1 1.10(17) . . . . ?
C17 C18 C13 C1 -178.64(10) . . . . ?
N1 C1 C13 C14 172.89(10) . . . . ?
C2 C1 C13 C14 -7.08(16) . . . . ?
N1 C1 C13 C18 -6.77(15) . . . . ?
C2 C1 C13 C18 173.26(10) . . . . ?
C18 C13 C14 C15 -0.28(16) . . . . ?
C1 C13 C14 C15 -179.95(10) . . . . ?
C13 C14 C15 C16 -0.93(18) . . . . ?
C13 C14 C15 Cl1 179.21(9) . . . . ?
C14 C15 C16 C17 0.69(18) . . . . ?
Cl1 C15 C16 C17 -179.44(9) . . . . ?
C15 C16 C17 C18 0.77(18) . . . . ?
O2 C18 C17 C16 178.26(11) . . . . ?
C13 C18 C17 C16 -1.97(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.051
# Attachment 'is_ag132.cif'

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

data_is_ag132
_database_code_depnum_ccdc_archive 'CCDC 835827'
#TrackingRef 'is_ag132.cif'

_audit_author_name               'Villinger, A.'
_audit_creation_method           SHELXL-97

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

# CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N3 O2'
_chemical_formula_sum            'C19 H15 N3 O2'
_chemical_formula_weight         317.34

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'

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

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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                   13.5332(7)
_cell_length_b                   11.4883(6)
_cell_length_c                   10.2680(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.013(2)
_cell_angle_gamma                90.00
_cell_volume                     1490.24(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2563
_cell_measurement_theta_min      5.535
_cell_measurement_theta_max      50.294

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9722
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17580
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4342
_reflns_number_gt                2638
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker Apex v2.0-2'
_computing_cell_refinement       'Bruker Apex v2.0-2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

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

# REFINEMENT DATA

_refine_special_details          
;
All H atoms (with exception of H1/H2) were positioned geometrically and
refined using a riding model , with C---H = 0.98 (methyl groups), 0.99\%A
(methylene groups), 1.00\%A (methine groups) or 0.95 \%A (aryl CH) and
with <i>U</i>~iso~(H) = 1.5 times <i>U</i>~eq~(C) (methyl groups) or with
<i>U</i>~iso~(H) = 1.2 times <i>U</i>~eq~(C) (methylene groups, aryl CH,
methine groups). Torsion angles of all methyl groups were allowed to refine.

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^ > 2\s(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^)+(0.0534P)^2^+0.0000P] 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         4342
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.02599(9) 0.64526(10) 0.26090(12) 0.0262(3) Uani 1 1 d . . .
N2 N 0.01499(9) 0.72596(10) 0.37075(12) 0.0285(3) Uani 1 1 d . . .
N3 N 0.15486(9) 0.71923(9) 0.59216(12) 0.0260(3) Uani 1 1 d . . .
O1 O -0.01295(8) 0.44670(8) 0.23194(11) 0.0370(3) Uani 1 1 d . . .
O2 O 0.23555(9) 0.90050(9) 0.73724(11) 0.0348(3) Uani 1 1 d . . .
C1 C 0.01659(10) 0.53544(11) 0.30259(15) 0.0268(3) Uani 1 1 d . . .
C2 C 0.09390(10) 0.55170(11) 0.44115(15) 0.0249(3) Uani 1 1 d . . .
C3 C 0.16113(11) 0.47845(12) 0.54161(15) 0.0270(3) Uani 1 1 d . . .
H3 H 0.1637 0.3973 0.5250 0.032 Uiso 1 1 calc R . .
C4 C 0.22380(11) 0.52731(12) 0.66562(15) 0.0267(3) Uani 1 1 d . . .
H4 H 0.2699 0.4792 0.7368 0.032 Uiso 1 1 calc R . .
C5 C 0.22079(10) 0.64840(12) 0.68899(14) 0.0248(3) Uani 1 1 d . . .
C6 C 0.09280(10) 0.66853(11) 0.47435(14) 0.0252(3) Uani 1 1 d . . .
C7 C -0.12843(11) 0.66772(11) 0.16078(14) 0.0252(3) Uani 1 1 d . . .
C8 C -0.16458(12) 0.60470(12) 0.03746(15) 0.0300(3) Uani 1 1 d . . .
H8 H -0.1192 0.5514 0.0156 0.036 Uiso 1 1 calc R . .
C9 C -0.26732(12) 0.62042(13) -0.05308(15) 0.0341(4) Uani 1 1 d . . .
H9 H -0.2930 0.5759 -0.1365 0.041 Uiso 1 1 calc R . .
C10 C -0.33330(12) 0.69961(13) -0.02441(16) 0.0338(4) Uani 1 1 d . . .
H10 H -0.4042 0.7089 -0.0868 0.041 Uiso 1 1 calc R . .
C11 C -0.29502(12) 0.76548(13) 0.09628(15) 0.0321(3) Uani 1 1 d . . .
H11 H -0.3394 0.8219 0.1151 0.039 Uiso 1 1 calc R . .
C12 C -0.19296(11) 0.75005(12) 0.18962(15) 0.0288(3) Uani 1 1 d . . .
H12 H -0.1672 0.7952 0.2725 0.035 Uiso 1 1 calc R . .
C13 C 0.28951(10) 0.70361(12) 0.81982(14) 0.0248(3) Uani 1 1 d . . .
C14 C 0.35369(11) 0.63679(13) 0.93287(15) 0.0283(3) Uani 1 1 d . . .
H14 H 0.3510 0.5545 0.9236 0.034 Uiso 1 1 calc R . .
C15 C 0.42044(11) 0.68384(13) 1.05665(15) 0.0295(3) Uani 1 1 d . . .
C16 C 0.42372(11) 0.80453(13) 1.06840(15) 0.0322(3) Uani 1 1 d . . .
H16 H 0.4693 0.8395 1.1523 0.039 Uiso 1 1 calc R . .
C17 C 0.36241(12) 0.87414(13) 0.96108(16) 0.0326(3) Uani 1 1 d . . .
H17 H 0.3667 0.9564 0.9715 0.039 Uiso 1 1 calc R . .
C18 C 0.29398(11) 0.82566(12) 0.83698(15) 0.0274(3) Uani 1 1 d . . .
C19 C 0.48648(12) 0.60703(14) 1.17475(16) 0.0378(4) Uani 1 1 d . . .
H19A H 0.4571 0.6078 1.2492 0.057 Uiso 1 1 calc R . .
H19B H 0.5594 0.6361 1.2112 0.057 Uiso 1 1 calc R . .
H19C H 0.4859 0.5273 1.1406 0.057 Uiso 1 1 calc R . .
H2 H 0.1907(15) 0.8537(19) 0.667(2) 0.072(6) Uiso 1 1 d . . .
H1 H 0.0238(14) 0.8030(18) 0.3421(19) 0.064(6) Uiso 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
N1 0.0294(6) 0.0189(6) 0.0269(6) -0.0026(5) 0.0059(5) -0.0006(5)
N2 0.0327(7) 0.0186(6) 0.0290(7) -0.0011(5) 0.0049(5) -0.0014(5)
N3 0.0284(6) 0.0206(6) 0.0286(6) 0.0004(5) 0.0097(5) -0.0008(5)
O1 0.0392(6) 0.0229(5) 0.0434(6) -0.0084(5) 0.0083(5) 0.0019(5)
O2 0.0461(7) 0.0229(5) 0.0320(6) 0.0004(4) 0.0100(5) 0.0007(5)
C1 0.0263(7) 0.0213(7) 0.0347(8) -0.0002(6) 0.0134(6) 0.0011(6)
C2 0.0241(7) 0.0210(6) 0.0314(7) -0.0003(6) 0.0121(6) 0.0006(5)
C3 0.0290(7) 0.0192(6) 0.0352(8) 0.0019(6) 0.0146(6) 0.0019(5)
C4 0.0260(7) 0.0219(7) 0.0310(8) 0.0048(6) 0.0088(6) 0.0037(5)
C5 0.0232(7) 0.0248(7) 0.0295(7) 0.0014(6) 0.0130(6) -0.0001(5)
C6 0.0260(7) 0.0212(7) 0.0298(7) 0.0026(6) 0.0118(6) 0.0001(5)
C7 0.0284(7) 0.0215(6) 0.0259(7) 0.0032(5) 0.0099(6) -0.0030(6)
C8 0.0367(8) 0.0272(7) 0.0273(8) 0.0005(6) 0.0129(7) 0.0004(6)
C9 0.0418(9) 0.0320(8) 0.0251(8) 0.0009(6) 0.0078(7) -0.0054(7)
C10 0.0307(8) 0.0348(8) 0.0310(8) 0.0058(7) 0.0052(7) -0.0027(7)
C11 0.0313(8) 0.0298(8) 0.0358(8) 0.0053(6) 0.0128(7) 0.0044(6)
C12 0.0323(8) 0.0258(7) 0.0287(8) -0.0002(6) 0.0115(6) -0.0008(6)
C13 0.0241(7) 0.0252(7) 0.0282(7) 0.0011(6) 0.0130(6) 0.0005(6)
C14 0.0280(8) 0.0263(7) 0.0329(8) 0.0011(6) 0.0137(6) 0.0009(6)
C15 0.0235(7) 0.0371(8) 0.0293(8) 0.0008(6) 0.0110(6) 0.0025(6)
C16 0.0302(8) 0.0379(8) 0.0296(8) -0.0055(7) 0.0122(6) -0.0019(7)
C17 0.0385(9) 0.0276(7) 0.0352(8) -0.0049(6) 0.0174(7) -0.0030(6)
C18 0.0299(8) 0.0261(7) 0.0293(8) 0.0021(6) 0.0143(6) 0.0013(6)
C19 0.0342(9) 0.0429(9) 0.0331(8) -0.0005(7) 0.0083(7) 0.0027(7)

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

# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3894(16) . ?
N1 N2 1.4110(15) . ?
N1 C7 1.4223(17) . ?
N2 C6 1.3684(17) . ?
N2 H1 0.95(2) . ?
N3 C6 1.3339(17) . ?
N3 C5 1.3456(17) . ?
O1 C1 1.2318(16) . ?
O2 C18 1.3537(17) . ?
O2 H2 0.93(2) . ?
C1 C2 1.444(2) . ?
C2 C6 1.3862(18) . ?
C2 C3 1.3881(19) . ?
C3 C4 1.3716(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.4147(19) . ?
C4 H4 0.9500 . ?
C5 C13 1.4751(19) . ?
C7 C8 1.3865(19) . ?
C7 C12 1.3895(19) . ?
C8 C9 1.379(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.4029(19) . ?
C13 C18 1.4118(19) . ?
C14 C15 1.3785(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(2) . ?
C15 C19 1.507(2) . ?
C16 C17 1.373(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.395(2) . ?
C17 H17 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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 N2 110.46(11) . . ?
C1 N1 C7 125.21(11) . . ?
N2 N1 C7 117.42(11) . . ?
C6 N2 N1 106.08(11) . . ?
C6 N2 H1 122.7(11) . . ?
N1 N2 H1 114.9(11) . . ?
C6 N3 C5 116.17(12) . . ?
C18 O2 H2 105.2(13) . . ?
O1 C1 N1 123.98(13) . . ?
O1 C1 C2 130.89(13) . . ?
N1 C1 C2 105.07(11) . . ?
C6 C2 C3 117.79(12) . . ?
C6 C2 C1 107.44(12) . . ?
C3 C2 C1 134.73(13) . . ?
C4 C3 C2 117.65(12) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 120.94(12) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
N3 C5 C4 121.41(12) . . ?
N3 C5 C13 116.58(12) . . ?
C4 C5 C13 122.02(12) . . ?
N3 C6 N2 123.59(12) . . ?
N3 C6 C2 125.95(12) . . ?
N2 C6 C2 110.41(12) . . ?
C8 C7 C12 120.47(13) . . ?
C8 C7 N1 119.91(12) . . ?
C12 C7 N1 119.58(12) . . ?
C9 C8 C7 119.17(14) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 121.06(14) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 119.26(14) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 120.74(14) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C7 119.21(14) . . ?
C11 C12 H12 120.4 . . ?
C7 C12 H12 120.4 . . ?
C14 C13 C18 117.00(12) . . ?
C14 C13 C5 121.29(12) . . ?
C18 C13 C5 121.70(12) . . ?
C15 C14 C13 123.71(13) . . ?
C15 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
C14 C15 C16 117.43(13) . . ?
C14 C15 C19 121.06(14) . . ?
C16 C15 C19 121.51(13) . . ?
C17 C16 C15 121.30(14) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 120.84(13) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
O2 C18 C17 117.00(13) . . ?
O2 C18 C13 123.30(12) . . ?
C17 C18 C13 119.69(13) . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C6 7.37(15) . . . . ?
C7 N1 N2 C6 159.84(11) . . . . ?
N2 N1 C1 O1 172.76(13) . . . . ?
C7 N1 C1 O1 22.9(2) . . . . ?
N2 N1 C1 C2 -4.72(15) . . . . ?
C7 N1 C1 C2 -154.58(12) . . . . ?
O1 C1 C2 C6 -176.91(15) . . . . ?
N1 C1 C2 C6 0.32(15) . . . . ?
O1 C1 C2 C3 0.5(3) . . . . ?
N1 C1 C2 C3 177.76(14) . . . . ?
C6 C2 C3 C4 -1.58(19) . . . . ?
C1 C2 C3 C4 -178.82(14) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C6 N3 C5 C4 0.35(18) . . . . ?
C6 N3 C5 C13 -179.82(11) . . . . ?
C3 C4 C5 N3 1.6(2) . . . . ?
C3 C4 C5 C13 -178.24(12) . . . . ?
C5 N3 C6 N2 174.00(12) . . . . ?
C5 N3 C6 C2 -3.1(2) . . . . ?
N1 N2 C6 N3 175.38(12) . . . . ?
N1 N2 C6 C2 -7.10(15) . . . . ?
C3 C2 C6 N3 3.8(2) . . . . ?
C1 C2 C6 N3 -178.23(13) . . . . ?
C3 C2 C6 N2 -173.63(12) . . . . ?
C1 C2 C6 N2 4.32(15) . . . . ?
C1 N1 C7 C8 -44.09(19) . . . . ?
N2 N1 C7 C8 167.91(12) . . . . ?
C1 N1 C7 C12 133.70(14) . . . . ?
N2 N1 C7 C12 -14.30(18) . . . . ?
C12 C7 C8 C9 -3.3(2) . . . . ?
N1 C7 C8 C9 174.47(12) . . . . ?
C7 C8 C9 C10 1.6(2) . . . . ?
C8 C9 C10 C11 1.0(2) . . . . ?
C9 C10 C11 C12 -2.0(2) . . . . ?
C10 C11 C12 C7 0.3(2) . . . . ?
C8 C7 C12 C11 2.3(2) . . . . ?
N1 C7 C12 C11 -175.45(12) . . . . ?
N3 C5 C13 C14 173.74(12) . . . . ?
C4 C5 C13 C14 -6.4(2) . . . . ?
N3 C5 C13 C18 -6.42(18) . . . . ?
C4 C5 C13 C18 173.42(13) . . . . ?
C18 C13 C14 C15 -0.8(2) . . . . ?
C5 C13 C14 C15 179.04(13) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C13 C14 C15 C19 179.32(13) . . . . ?
C14 C15 C16 C17 0.3(2) . . . . ?
C19 C15 C16 C17 -179.19(14) . . . . ?
C15 C16 C17 C18 0.6(2) . . . . ?
C16 C17 C18 O2 179.25(12) . . . . ?
C16 C17 C18 C13 -1.6(2) . . . . ?
C14 C13 C18 O2 -179.24(12) . . . . ?
C5 C13 C18 O2 0.9(2) . . . . ?
C14 C13 C18 C17 1.69(19) . . . . ?
C5 C13 C18 C17 -178.16(13) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.060
# Attachment 'is_ag140.cif'

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

data_is_ag140
_database_code_depnum_ccdc_archive 'CCDC 835828'
#TrackingRef 'is_ag140.cif'

_audit_author_name               'Villinger, A.'
_audit_creation_method           SHELXL-97

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

# CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 N3 O'
_chemical_formula_sum            'C20 H17 N3 O'
_chemical_formula_weight         315.37

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'

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

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   12.7467(5)
_cell_length_b                   16.7588(6)
_cell_length_c                   7.5184(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.053(2)
_cell_angle_gamma                90.00
_cell_volume                     1550.96(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6088
_cell_measurement_theta_min      4.861
_cell_measurement_theta_max      60.996

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9425
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16781
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         28.99
_reflns_number_total             4114
_reflns_number_gt                3182
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker Apex v2.0-2'
_computing_cell_refinement       'Bruker Apex v2.0-2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

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

# REFINEMENT DATA

_refine_special_details          
;
All H atoms (with exception of H1) were positioned geometrically and
refined using a riding model , with C---H = 0.98 (methyl groups), 0.99\%A
(methylene groups), 1.00\%A (methine groups) or 0.95 \%A (aryl CH) and
with <i>U</i>~iso~(H) = 1.5 times <i>U</i>~eq~(C) (methyl groups) or with
<i>U</i>~iso~(H) = 1.2 times <i>U</i>~eq~(C) (methylene groups, aryl CH,
methine groups). Torsion angles of all methyl groups were allowed to refine.
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^ > 2\s(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^)+(0.0677P)^2^+0.1925P] 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         4114
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.00320(8) 0.71151(5) 0.61482(14) 0.0351(2) Uani 1 1 d . . .
N1 N 0.08576(7) 0.58924(5) 0.80767(13) 0.0215(2) Uani 1 1 d . . .
N2 N 0.33712(8) 0.52758(6) 1.10540(14) 0.0262(2) Uani 1 1 d . . .
N3 N 0.26696(8) 0.58510(6) 1.00929(14) 0.0244(2) Uani 1 1 d . . .
C1 C -0.00150(9) 0.54380(7) 0.73154(15) 0.0204(2) Uani 1 1 d . . .
C2 C -0.00317(9) 0.46090(7) 0.76923(16) 0.0229(2) Uani 1 1 d . . .
H2 H -0.0663 0.4307 0.7143 0.027 Uiso 1 1 calc R . .
C3 C 0.08492(9) 0.42345(7) 0.88376(16) 0.0234(2) Uani 1 1 d . . .
H3 H 0.0837 0.3679 0.9080 0.028 Uiso 1 1 calc R . .
C4 C 0.17642(9) 0.46984(7) 0.96337(15) 0.0217(2) Uani 1 1 d . . .
C5 C 0.28368(9) 0.45908(7) 1.07908(16) 0.0233(2) Uani 1 1 d . . .
C6 C 0.16990(9) 0.55149(7) 0.92007(15) 0.0211(2) Uani 1 1 d . . .
C7 C -0.09411(9) 0.58530(6) 0.60519(15) 0.0206(2) Uani 1 1 d . . .
C8 C -0.08651(9) 0.66571(7) 0.55156(16) 0.0240(2) Uani 1 1 d . . .
C9 C -0.17405(10) 0.70115(7) 0.42632(17) 0.0287(3) Uani 1 1 d . . .
H9 H -0.1679 0.7546 0.3883 0.034 Uiso 1 1 calc R . .
C10 C -0.26957(10) 0.65989(7) 0.35658(16) 0.0277(3) Uani 1 1 d . . .
H10 H -0.3284 0.6855 0.2722 0.033 Uiso 1 1 calc R . .
C11 C -0.28095(10) 0.58107(7) 0.40832(16) 0.0259(3) Uani 1 1 d . . .
C12 C -0.19261(9) 0.54564(7) 0.53022(16) 0.0239(2) Uani 1 1 d . . .
H12 H -0.1992 0.4917 0.5647 0.029 Uiso 1 1 calc R . .
C13 C -0.38573(11) 0.53600(9) 0.3369(2) 0.0379(3) Uani 1 1 d . . .
H13A H -0.3720 0.4878 0.2726 0.057 Uiso 1 1 calc R . .
H13B H -0.4382 0.5699 0.2514 0.057 Uiso 1 1 calc R . .
H13C H -0.4152 0.5209 0.4403 0.057 Uiso 1 1 calc R . .
C14 C 0.33706(10) 0.38404(7) 1.16404(18) 0.0286(3) Uani 1 1 d . . .
H14A H 0.4124 0.3954 1.2309 0.043 Uiso 1 1 calc R . .
H14B H 0.3361 0.3446 1.0673 0.043 Uiso 1 1 calc R . .
H14C H 0.2978 0.3628 1.2498 0.043 Uiso 1 1 calc R . .
C15 C 0.30333(9) 0.66464(7) 0.99963(16) 0.0234(2) Uani 1 1 d . . .
C16 C 0.40689(10) 0.67792(7) 0.97804(17) 0.0276(3) Uani 1 1 d . . .
H16 H 0.4534 0.6343 0.9720 0.033 Uiso 1 1 calc R . .
C17 C 0.44157(11) 0.75578(8) 0.96544(18) 0.0330(3) Uani 1 1 d . . .
H17 H 0.5123 0.7655 0.9511 0.040 Uiso 1 1 calc R . .
C18 C 0.37350(12) 0.81921(8) 0.97368(18) 0.0350(3) Uani 1 1 d . . .
H18 H 0.3971 0.8724 0.9631 0.042 Uiso 1 1 calc R . .
C19 C 0.27099(11) 0.80510(7) 0.99741(18) 0.0323(3) Uani 1 1 d . . .
H19 H 0.2249 0.8489 1.0046 0.039 Uiso 1 1 calc R . .
C20 C 0.23479(10) 0.72783(7) 1.01088(16) 0.0266(3) Uani 1 1 d . . .
H20 H 0.1645 0.7183 1.0275 0.032 Uiso 1 1 calc R . .
H1 H 0.0510(16) 0.6818(11) 0.697(3) 0.065(6) Uiso 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
O1 0.0269(5) 0.0251(4) 0.0455(6) 0.0079(4) -0.0049(4) -0.0047(4)
N1 0.0173(4) 0.0221(4) 0.0243(5) 0.0010(4) 0.0039(4) 0.0005(4)
N2 0.0204(5) 0.0264(5) 0.0297(5) 0.0025(4) 0.0024(4) 0.0043(4)
N3 0.0175(5) 0.0229(5) 0.0300(5) 0.0025(4) 0.0009(4) 0.0008(4)
C1 0.0181(5) 0.0231(5) 0.0201(5) -0.0007(4) 0.0050(4) 0.0014(4)
C2 0.0204(5) 0.0221(5) 0.0250(6) -0.0019(4) 0.0039(4) -0.0017(4)
C3 0.0237(6) 0.0212(5) 0.0252(6) 0.0008(4) 0.0064(5) 0.0018(4)
C4 0.0203(5) 0.0230(5) 0.0221(5) 0.0013(4) 0.0061(4) 0.0031(4)
C5 0.0195(5) 0.0256(5) 0.0240(6) 0.0005(4) 0.0041(4) 0.0037(4)
C6 0.0177(5) 0.0229(5) 0.0222(5) -0.0005(4) 0.0043(4) 0.0011(4)
C7 0.0188(5) 0.0229(5) 0.0195(5) -0.0007(4) 0.0040(4) 0.0024(4)
C8 0.0224(6) 0.0233(5) 0.0251(6) -0.0010(4) 0.0039(4) 0.0003(4)
C9 0.0302(6) 0.0232(5) 0.0292(6) 0.0015(5) 0.0017(5) 0.0041(5)
C10 0.0252(6) 0.0311(6) 0.0232(6) -0.0002(5) -0.0002(5) 0.0065(5)
C11 0.0210(6) 0.0313(6) 0.0233(6) -0.0022(5) 0.0019(5) 0.0012(5)
C12 0.0217(6) 0.0244(5) 0.0246(6) -0.0001(4) 0.0041(5) -0.0001(4)
C13 0.0247(6) 0.0424(8) 0.0398(8) 0.0031(6) -0.0040(6) -0.0044(5)
C14 0.0254(6) 0.0263(6) 0.0309(6) 0.0026(5) 0.0020(5) 0.0063(5)
C15 0.0218(5) 0.0241(5) 0.0218(5) -0.0001(4) 0.0009(4) -0.0019(4)
C16 0.0227(6) 0.0320(6) 0.0273(6) -0.0017(5) 0.0049(5) -0.0008(5)
C17 0.0286(6) 0.0383(7) 0.0311(7) 0.0000(5) 0.0060(5) -0.0092(5)
C18 0.0425(8) 0.0277(6) 0.0309(7) 0.0004(5) 0.0028(6) -0.0090(6)
C19 0.0352(7) 0.0252(6) 0.0322(7) -0.0008(5) 0.0008(5) 0.0025(5)
C20 0.0225(6) 0.0278(6) 0.0273(6) -0.0014(5) 0.0024(5) 0.0010(5)

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

# MOLECULAR GEOMETRY

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C8 1.3566(14) . ?
O1 H1 0.90(2) . ?
N1 C6 1.3394(14) . ?
N1 C1 1.3469(14) . ?
N2 C5 1.3232(15) . ?
N2 N3 1.3840(13) . ?
N3 C6 1.3663(14) . ?
N3 C15 1.4193(14) . ?
C1 C2 1.4191(15) . ?
C1 C7 1.4823(15) . ?
C2 C3 1.3763(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.4001(16) . ?
C3 H3 0.9500 . ?
C4 C6 1.4040(15) . ?
C4 C5 1.4285(16) . ?
C5 C14 1.4923(15) . ?
C7 C12 1.4030(15) . ?
C7 C8 1.4171(16) . ?
C8 C9 1.3924(16) . ?
C9 C10 1.3799(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.3952(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.3872(16) . ?
C11 C13 1.5068(17) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.3891(17) . ?
C15 C20 1.3894(16) . ?
C16 C17 1.3887(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.3872(17) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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 O1 H1 106.6(12) . . ?
C6 N1 C1 116.02(9) . . ?
C5 N2 N3 106.77(9) . . ?
C6 N3 N2 110.43(9) . . ?
C6 N3 C15 128.93(9) . . ?
N2 N3 C15 120.36(9) . . ?
N1 C1 C2 121.48(10) . . ?
N1 C1 C7 116.06(10) . . ?
C2 C1 C7 122.45(10) . . ?
C3 C2 C1 121.29(10) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 117.90(10) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C3 C4 C6 116.71(10) . . ?
C3 C4 C5 138.55(11) . . ?
C6 C4 C5 104.70(10) . . ?
N2 C5 C4 110.84(10) . . ?
N2 C5 C14 120.49(10) . . ?
C4 C5 C14 128.67(11) . . ?
N1 C6 N3 126.12(10) . . ?
N1 C6 C4 126.59(10) . . ?
N3 C6 C4 107.25(9) . . ?
C12 C7 C8 117.16(10) . . ?
C12 C7 C1 121.05(10) . . ?
C8 C7 C1 121.78(10) . . ?
O1 C8 C9 116.76(10) . . ?
O1 C8 C7 123.50(10) . . ?
C9 C8 C7 119.74(10) . . ?
C10 C9 C8 121.08(11) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 120.92(11) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 117.66(11) . . ?
C12 C11 C13 120.87(11) . . ?
C10 C11 C13 121.47(11) . . ?
C11 C12 C7 123.42(11) . . ?
C11 C12 H12 118.3 . . ?
C7 C12 H12 118.3 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 121.11(11) . . ?
C16 C15 N3 119.31(10) . . ?
C20 C15 N3 119.59(11) . . ?
C17 C16 C15 119.18(12) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C18 C17 C16 120.29(12) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.89(12) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 120.79(12) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C15 118.74(12) . . ?
C19 C20 H20 120.6 . . ?
C15 C20 H20 120.6 . . ?

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
C5 N2 N3 C6 -1.10(13) . . . . ?
C5 N2 N3 C15 -175.48(10) . . . . ?
C6 N1 C1 C2 -0.02(16) . . . . ?
C6 N1 C1 C7 -179.22(10) . . . . ?
N1 C1 C2 C3 -0.69(17) . . . . ?
C7 C1 C2 C3 178.45(11) . . . . ?
C1 C2 C3 C4 0.42(17) . . . . ?
C2 C3 C4 C6 0.49(16) . . . . ?
C2 C3 C4 C5 -176.82(13) . . . . ?
N3 N2 C5 C4 0.30(13) . . . . ?
N3 N2 C5 C14 179.63(10) . . . . ?
C3 C4 C5 N2 178.07(13) . . . . ?
C6 C4 C5 N2 0.56(13) . . . . ?
C3 C4 C5 C14 -1.2(2) . . . . ?
C6 C4 C5 C14 -178.69(12) . . . . ?
C1 N1 C6 N3 178.75(11) . . . . ?
C1 N1 C6 C4 1.05(17) . . . . ?
N2 N3 C6 N1 -176.61(10) . . . . ?
C15 N3 C6 N1 -2.8(2) . . . . ?
N2 N3 C6 C4 1.46(13) . . . . ?
C15 N3 C6 C4 175.22(11) . . . . ?
C3 C4 C6 N1 -1.31(18) . . . . ?
C5 C4 C6 N1 176.85(11) . . . . ?
C3 C4 C6 N3 -179.36(10) . . . . ?
C5 C4 C6 N3 -1.20(13) . . . . ?
N1 C1 C7 C12 -174.55(10) . . . . ?
C2 C1 C7 C12 6.26(17) . . . . ?
N1 C1 C7 C8 6.92(16) . . . . ?
C2 C1 C7 C8 -172.27(11) . . . . ?
C12 C7 C8 O1 179.18(11) . . . . ?
C1 C7 C8 O1 -2.23(18) . . . . ?
C12 C7 C8 C9 -1.37(17) . . . . ?
C1 C7 C8 C9 177.22(11) . . . . ?
O1 C8 C9 C10 -178.86(11) . . . . ?
C7 C8 C9 C10 1.66(19) . . . . ?
C8 C9 C10 C11 -0.6(2) . . . . ?
C9 C10 C11 C12 -0.73(18) . . . . ?
C9 C10 C11 C13 178.44(12) . . . . ?
C10 C11 C12 C7 1.00(18) . . . . ?
C13 C11 C12 C7 -178.18(12) . . . . ?
C8 C7 C12 C11 0.05(18) . . . . ?
C1 C7 C12 C11 -178.55(11) . . . . ?
C6 N3 C15 C16 -133.60(13) . . . . ?
N2 N3 C15 C16 39.62(16) . . . . ?
C6 N3 C15 C20 46.05(18) . . . . ?
N2 N3 C15 C20 -140.72(11) . . . . ?
C20 C15 C16 C17 -0.75(18) . . . . ?
N3 C15 C16 C17 178.90(11) . . . . ?
C15 C16 C17 C18 -0.23(19) . . . . ?
C16 C17 C18 C19 1.0(2) . . . . ?
C17 C18 C19 C20 -0.8(2) . . . . ?
C18 C19 C20 C15 -0.17(19) . . . . ?
C16 C15 C20 C19 0.94(18) . . . . ?
N3 C15 C20 C19 -178.71(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.046
# Attachment 'is_ag148.cif'

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

data_av_ag148
_database_code_depnum_ccdc_archive 'CCDC 835829'
#TrackingRef 'is_ag148.cif'

_audit_author_name               'Villinger, A.'
_audit_creation_method           SHELXL-97

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

# CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 Cl N3 O S'
_chemical_formula_sum            'C17 H16 Cl N3 O S'
_chemical_formula_weight         345.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

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                   7.0888(4)
_cell_length_b                   24.9100(13)
_cell_length_c                   8.8454(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.728(3)
_cell_angle_gamma                90.00
_cell_volume                     1529.33(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2982
_cell_measurement_theta_min      6.093
_cell_measurement_theta_max      56.651

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8615
_exptl_absorpt_correction_T_max  0.9729
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17093
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4447
_reflns_number_gt                3242
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker Apex v2.0-2'
_computing_cell_refinement       'Bruker Apex v2.0-2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

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

# REFINEMENT DATA

_refine_special_details          
;
All H atoms (with exception of H1) were positioned geometrically and
refined using a riding model , with C---H = 0.98 (methyl groups), 0.99\%A
(methylene groups), 1.00\%A (methine groups) or 0.95 \%A (aryl CH) and
with <i>U</i>~iso~(H) = 1.5 times <i>U</i>~eq~(C) (methyl groups) or with
<i>U</i>~iso~(H) = 1.2 times <i>U</i>~eq~(C) (methylene groups, aryl CH,
methine groups). Torsion angles of all methyl groups were allowed to refine.

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^ > 2\s(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^)+(0.0398P)^2^+0.1497P] 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         4447
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0933
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
S1 S 0.34414(6) 0.122960(17) 0.50172(5) 0.02079(10) Uani 1 1 d . . .
Cl1 Cl 0.10419(6) -0.162042(17) -0.21127(5) 0.02778(12) Uani 1 1 d . . .
C1 C 0.5970(2) 0.11916(6) 0.51884(17) 0.0170(3) Uani 1 1 d . . .
C2 C 0.3229(2) 0.06748(6) 0.38168(18) 0.0176(3) Uani 1 1 d . . .
C12 C 0.4139(2) -0.05936(6) 0.09246(17) 0.0164(3) Uani 1 1 d . . .
C16 C 0.2965(2) -0.12756(7) -0.09796(18) 0.0201(3) Uani 1 1 d . . .
C13 C 0.6036(2) -0.07453(6) 0.08397(18) 0.0182(3) Uani 1 1 d . . .
C17 C 0.2612(2) -0.08681(6) -0.00361(17) 0.0186(3) Uani 1 1 d . . .
H17 H 0.1320 -0.0769 -0.0029 0.022 Uiso 1 1 calc R . .
C5 C 0.3747(2) -0.01583(6) 0.19498(17) 0.0164(3) Uani 1 1 d . . .
C6 C 0.5074(2) 0.05083(6) 0.36536(17) 0.0165(3) Uani 1 1 d . . .
C4 C 0.1891(2) -0.00175(6) 0.21124(18) 0.0195(3) Uani 1 1 d . . .
H4 H 0.0813 -0.0211 0.1563 0.023 Uiso 1 1 calc R . .
C3 C 0.1614(2) 0.04012(6) 0.30662(18) 0.0196(3) Uani 1 1 d . . .
H3 H 0.0362 0.0497 0.3201 0.024 Uiso 1 1 calc R . .
C10 C 0.7509(2) 0.24034(7) 0.7569(2) 0.0239(4) Uani 1 1 d . . .
H10A H 0.7001 0.2598 0.8378 0.029 Uiso 1 1 calc R . .
H10B H 0.7438 0.2648 0.6677 0.029 Uiso 1 1 calc R . .
C11 C 0.6269(2) 0.19145(7) 0.70697(18) 0.0202(3) Uani 1 1 d . . .
H11A H 0.6122 0.1708 0.7995 0.024 Uiso 1 1 calc R . .
H11B H 0.4972 0.2032 0.6532 0.024 Uiso 1 1 calc R . .
C8 C 1.0364(2) 0.19373(7) 0.69725(19) 0.0238(4) Uani 1 1 d . . .
H8A H 1.0325 0.2167 0.6052 0.029 Uiso 1 1 calc R . .
H8B H 1.1721 0.1834 0.7378 0.029 Uiso 1 1 calc R . .
C9 C 0.9607(2) 0.22516(7) 0.81957(19) 0.0226(3) Uani 1 1 d . . .
H9A H 1.0388 0.2580 0.8470 0.027 Uiso 1 1 calc R . .
H9B H 0.9704 0.2031 0.9139 0.027 Uiso 1 1 calc R . .
C15 C 0.4829(2) -0.14277(7) -0.10446(19) 0.0223(3) Uani 1 1 d . . .
H15 H 0.5054 -0.1711 -0.1704 0.027 Uiso 1 1 calc R . .
C14 C 0.6348(2) -0.11600(7) -0.01350(18) 0.0211(3) Uani 1 1 d . . .
H14 H 0.7630 -0.1260 -0.0174 0.025 Uiso 1 1 calc R . .
C7 C 0.9167(2) 0.14368(7) 0.6513(2) 0.0225(4) Uani 1 1 d . . .
H7A H 0.9610 0.1257 0.5649 0.027 Uiso 1 1 calc R . .
H7B H 0.9358 0.1185 0.7397 0.027 Uiso 1 1 calc R . .
N2 N 0.71020(19) 0.15655(5) 0.60394(15) 0.0192(3) Uani 1 1 d . . .
N1 N 0.66096(18) 0.07990(5) 0.44562(15) 0.0183(3) Uani 1 1 d . . .
N3 N 0.53266(18) 0.00986(5) 0.27498(14) 0.0166(3) Uani 1 1 d . . .
O1 O 0.76079(16) -0.05037(5) 0.16770(14) 0.0227(3) Uani 1 1 d . . .
H1 H 0.717(3) -0.0231(10) 0.219(3) 0.050(7) Uiso 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
S1 0.01372(19) 0.0228(2) 0.0262(2) -0.00509(16) 0.00502(15) 0.00042(15)
Cl1 0.0264(2) 0.0285(2) 0.0264(2) -0.00594(17) 0.00054(16) -0.00855(17)
C1 0.0134(7) 0.0209(8) 0.0166(8) 0.0023(6) 0.0028(6) 0.0003(6)
C2 0.0153(7) 0.0186(8) 0.0191(8) 0.0001(6) 0.0043(6) 0.0007(6)
C12 0.0146(7) 0.0177(7) 0.0168(8) 0.0036(6) 0.0032(6) 0.0001(6)
C16 0.0204(8) 0.0208(8) 0.0176(8) 0.0012(6) 0.0003(6) -0.0045(6)
C13 0.0149(7) 0.0199(8) 0.0192(8) 0.0030(6) 0.0020(6) -0.0004(6)
C17 0.0151(8) 0.0205(8) 0.0202(8) 0.0018(6) 0.0034(6) -0.0005(6)
C5 0.0140(7) 0.0173(7) 0.0171(8) 0.0022(6) 0.0016(6) -0.0013(6)
C6 0.0146(7) 0.0190(7) 0.0157(7) 0.0026(6) 0.0031(6) -0.0004(6)
C4 0.0132(7) 0.0211(8) 0.0237(8) -0.0007(6) 0.0022(6) -0.0029(6)
C3 0.0123(7) 0.0219(8) 0.0251(9) 0.0009(6) 0.0051(6) 0.0001(6)
C10 0.0228(9) 0.0213(8) 0.0261(9) -0.0034(7) 0.0014(7) 0.0021(7)
C11 0.0163(8) 0.0216(8) 0.0232(8) -0.0023(6) 0.0052(6) 0.0014(6)
C8 0.0177(8) 0.0285(9) 0.0246(9) -0.0042(7) 0.0029(7) -0.0029(7)
C9 0.0204(8) 0.0224(8) 0.0229(9) -0.0019(6) -0.0002(6) -0.0009(7)
C15 0.0252(9) 0.0206(8) 0.0213(9) -0.0015(6) 0.0049(7) 0.0018(7)
C14 0.0171(8) 0.0233(8) 0.0233(8) 0.0013(6) 0.0050(6) 0.0047(6)
C7 0.0126(7) 0.0259(8) 0.0281(9) -0.0071(7) 0.0022(6) 0.0016(6)
N2 0.0140(6) 0.0221(7) 0.0214(7) -0.0045(5) 0.0029(5) 0.0000(5)
N1 0.0140(6) 0.0207(7) 0.0195(7) -0.0016(5) 0.0021(5) -0.0008(5)
N3 0.0127(6) 0.0195(6) 0.0172(7) 0.0004(5) 0.0022(5) -0.0002(5)
O1 0.0121(5) 0.0269(6) 0.0283(7) -0.0059(5) 0.0023(5) -0.0009(5)

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

# MOLECULAR GEOMETRY

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
S1 C2 1.7305(16) . ?
S1 C1 1.7703(16) . ?
Cl1 C16 1.7450(16) . ?
C1 N1 1.304(2) . ?
C1 N2 1.354(2) . ?
C2 C3 1.381(2) . ?
C2 C6 1.407(2) . ?
C12 C17 1.410(2) . ?
C12 C13 1.414(2) . ?
C12 C5 1.476(2) . ?
C16 C17 1.369(2) . ?
C16 C15 1.387(2) . ?
C13 O1 1.3478(18) . ?
C13 C14 1.392(2) . ?
C17 H17 0.9500 . ?
C5 N3 1.3571(19) . ?
C5 C4 1.397(2) . ?
C6 N3 1.331(2) . ?
C6 N1 1.3781(19) . ?
C4 C3 1.380(2) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C10 C11 1.514(2) . ?
C10 C9 1.525(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N2 1.467(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C8 C7 1.516(2) . ?
C8 C9 1.519(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C15 C14 1.378(2) . ?
C15 H15 0.9500 . ?
C14 H14 0.9500 . ?
C7 N2 1.4740(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O1 H1 0.90(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
C2 S1 C1 88.29(7) . . ?
N1 C1 N2 124.42(14) . . ?
N1 C1 S1 116.48(12) . . ?
N2 C1 S1 119.10(12) . . ?
C3 C2 C6 120.14(15) . . ?
C3 C2 S1 130.50(12) . . ?
C6 C2 S1 109.36(11) . . ?
C17 C12 C13 117.41(14) . . ?
C17 C12 C5 120.63(14) . . ?
C13 C12 C5 121.94(13) . . ?
C17 C16 C15 121.42(15) . . ?
C17 C16 Cl1 119.80(13) . . ?
C15 C16 Cl1 118.77(13) . . ?
O1 C13 C14 117.02(14) . . ?
O1 C13 C12 122.71(14) . . ?
C14 C13 C12 120.27(14) . . ?
C16 C17 C12 120.95(15) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
N3 C5 C4 121.49(14) . . ?
N3 C5 C12 115.38(13) . . ?
C4 C5 C12 123.13(14) . . ?
N3 C6 N1 121.59(14) . . ?
N3 C6 C2 121.94(14) . . ?
N1 C6 C2 116.46(14) . . ?
C3 C4 C5 120.44(14) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C3 C2 117.37(14) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C11 C10 C9 111.82(14) . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
N2 C11 C10 112.03(13) . . ?
N2 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
N2 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C7 C8 C9 110.80(14) . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C10 109.19(13) . . ?
C8 C9 H9A 109.8 . . ?
C10 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
C10 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
C14 C15 C16 118.80(15) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C14 C13 121.13(15) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
N2 C7 C8 111.51(14) . . ?
N2 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C1 N2 C11 119.02(13) . . ?
C1 N2 C7 116.80(13) . . ?
C11 N2 C7 116.99(13) . . ?
C1 N1 C6 109.38(13) . . ?
C6 N3 C5 118.51(13) . . ?
C13 O1 H1 106.3(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
C2 S1 C1 N1 -1.34(13) . . . . ?
C2 S1 C1 N2 178.07(13) . . . . ?
C1 S1 C2 C3 -179.69(16) . . . . ?
C1 S1 C2 C6 0.21(12) . . . . ?
C17 C12 C13 O1 178.51(14) . . . . ?
C5 C12 C13 O1 -0.3(2) . . . . ?
C17 C12 C13 C14 -1.6(2) . . . . ?
C5 C12 C13 C14 179.64(14) . . . . ?
C15 C16 C17 C12 -1.0(2) . . . . ?
Cl1 C16 C17 C12 178.13(12) . . . . ?
C13 C12 C17 C16 1.8(2) . . . . ?
C5 C12 C17 C16 -179.39(14) . . . . ?
C17 C12 C5 N3 -176.12(13) . . . . ?
C13 C12 C5 N3 2.6(2) . . . . ?
C17 C12 C5 C4 4.4(2) . . . . ?
C13 C12 C5 C4 -176.79(14) . . . . ?
C3 C2 C6 N3 2.0(2) . . . . ?
S1 C2 C6 N3 -177.87(12) . . . . ?
C3 C2 C6 N1 -179.22(14) . . . . ?
S1 C2 C6 N1 0.87(17) . . . . ?
N3 C5 C4 C3 2.0(2) . . . . ?
C12 C5 C4 C3 -178.65(15) . . . . ?
C5 C4 C3 C2 1.1(2) . . . . ?
C6 C2 C3 C4 -3.0(2) . . . . ?
S1 C2 C3 C4 176.91(13) . . . . ?
C9 C10 C11 N2 -50.60(19) . . . . ?
C7 C8 C9 C10 -58.51(18) . . . . ?
C11 C10 C9 C8 57.08(19) . . . . ?
C17 C16 C15 C14 0.0(2) . . . . ?
Cl1 C16 C15 C14 -179.18(12) . . . . ?
C16 C15 C14 C13 0.2(2) . . . . ?
O1 C13 C14 C15 -179.48(15) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C9 C8 C7 N2 53.77(19) . . . . ?
N1 C1 N2 C11 -166.98(15) . . . . ?
S1 C1 N2 C11 13.67(19) . . . . ?
N1 C1 N2 C7 -17.5(2) . . . . ?
S1 C1 N2 C7 163.17(12) . . . . ?
C10 C11 N2 C1 -163.44(14) . . . . ?
C10 C11 N2 C7 47.11(19) . . . . ?
C8 C7 N2 C1 161.08(14) . . . . ?
C8 C7 N2 C11 -48.8(2) . . . . ?
N2 C1 N1 C6 -177.37(14) . . . . ?
S1 C1 N1 C6 2.00(17) . . . . ?
N3 C6 N1 C1 176.91(14) . . . . ?
C2 C6 N1 C1 -1.84(19) . . . . ?
N1 C6 N3 C5 -177.69(13) . . . . ?
C2 C6 N3 C5 1.0(2) . . . . ?
C4 C5 N3 C6 -3.0(2) . . . . ?
C12 C5 N3 C6 177.59(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.065
# Attachment 'is_ag188.cif'

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

data_is_ag188
_database_code_depnum_ccdc_archive 'CCDC 835830'
#TrackingRef 'is_ag188.cif'

_audit_author_name               'Villinger, A.'
_audit_creation_method           SHELXL-97

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

# CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 N3 O S'
_chemical_formula_sum            'C18 H19 N3 O S'
_chemical_formula_weight         325.42

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

# CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19

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

_cell_length_a                   6.3395(2)
_cell_length_b                   7.8493(3)
_cell_length_c                   31.3577(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1560.38(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4335
_cell_measurement_theta_min      5.196
_cell_measurement_theta_max      60.852

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9148
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14344
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4521
_reflns_number_gt                3876
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker Apex v2.0-2'
_computing_cell_refinement       'Bruker Apex v2.0-2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

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

# REFINEMENT DATA

_refine_special_details          
;
All H atoms were positioned geometrically and refined using a riding model,
with C---H = 0.98 (methyl groups), 0.99\%A
(methylene groups), 1.00\%A (methine groups) or 0.95 \%A (aryl CH) and
with <i>U</i>~iso~(H) = 1.5 times <i>U</i>~eq~(C) (methyl groups) or with
<i>U</i>~iso~(H) = 1.2 times <i>U</i>~eq~(C) (methylene groups, aryl CH,
methine groups). Torsion angles of all methyl groups were allowed to refine.

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^ > 2\s(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^)+(0.0403P)^2^+0.0651P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(6)
_refine_ls_number_reflns         4521
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
S1 S 0.50288(7) 0.40480(5) 0.779682(12) 0.02429(9) Uani 1 1 d . . .
N1 N 0.2030(2) 0.18180(16) 0.87233(4) 0.0195(3) Uani 1 1 d . . .
N2 N 0.1458(2) 0.25126(15) 0.79942(4) 0.0206(3) Uani 1 1 d . . .
N3 N 0.1672(2) 0.34977(17) 0.72872(4) 0.0255(3) Uani 1 1 d . . .
O1 O 0.06722(18) -0.13508(15) 1.05842(3) 0.0253(3) Uani 1 1 d . . .
C1 C 0.2706(2) 0.25068(18) 0.83568(5) 0.0190(3) Uani 1 1 d . . .
C2 C 0.4731(3) 0.32525(17) 0.83112(4) 0.0207(3) Uani 1 1 d . . .
C3 C 0.2458(3) 0.32724(19) 0.76794(5) 0.0207(3) Uani 1 1 d . . .
C4 C 0.6129(3) 0.3219(2) 0.86475(5) 0.0247(3) Uani 1 1 d . . .
H4 H 0.7511 0.3675 0.8622 0.030 Uiso 1 1 calc R . .
C5 C 0.5436(2) 0.24937(19) 0.90250(5) 0.0227(3) Uani 1 1 d . . .
H5 H 0.6355 0.2448 0.9264 0.027 Uiso 1 1 calc R . .
C6 C 0.3391(2) 0.18267(19) 0.90578(5) 0.0189(3) Uani 1 1 d . . .
C7 C 0.2612(2) 0.10562(19) 0.94609(5) 0.0188(3) Uani 1 1 d . . .
C8 C 0.3934(3) 0.0855(2) 0.98173(5) 0.0237(3) Uani 1 1 d . . .
H8 H 0.5340 0.1272 0.9806 0.028 Uiso 1 1 calc R . .
C9 C 0.3227(3) 0.0061(2) 1.01831(5) 0.0249(3) Uani 1 1 d . . .
H9 H 0.4154 -0.0066 1.0419 0.030 Uiso 1 1 calc R . .
C10 C 0.1177(3) -0.05523(19) 1.02104(5) 0.0202(3) Uani 1 1 d . . .
C11 C -0.0192(3) -0.03353(17) 0.98657(4) 0.0197(3) Uani 1 1 d . . .
H11 H -0.1608 -0.0727 0.9882 0.024 Uiso 1 1 calc R . .
C12 C 0.0548(2) 0.04638(18) 0.94975(5) 0.0192(3) Uani 1 1 d . . .
H12 H -0.0387 0.0609 0.9264 0.023 Uiso 1 1 calc R . .
C13 C -0.1519(3) -0.1562(2) 1.06787(5) 0.0260(4) Uani 1 1 d . . .
H13A H -0.2175 -0.2279 1.0460 0.039 Uiso 1 1 calc R . .
H13B H -0.2210 -0.0445 1.0683 0.039 Uiso 1 1 calc R . .
H13C H -0.1674 -0.2106 1.0958 0.039 Uiso 1 1 calc R . .
C14 C 0.2769(3) 0.4421(2) 0.69464(5) 0.0267(4) Uani 1 1 d . . .
H14A H 0.4187 0.4766 0.7046 0.032 Uiso 1 1 calc R . .
H14B H 0.1971 0.5465 0.6873 0.032 Uiso 1 1 calc R . .
C15 C 0.2981(3) 0.3297(2) 0.65516(5) 0.0258(4) Uani 1 1 d . . .
H15A H 0.3615 0.3965 0.6316 0.031 Uiso 1 1 calc R . .
H15B H 0.3929 0.2328 0.6615 0.031 Uiso 1 1 calc R . .
C16 C 0.0831(3) 0.2626(2) 0.64135(5) 0.0285(4) Uani 1 1 d . . .
H16A H 0.1009 0.1831 0.6171 0.034 Uiso 1 1 calc R . .
H16B H -0.0060 0.3587 0.6317 0.034 Uiso 1 1 calc R . .
C17 C -0.0258(3) 0.17053(19) 0.67822(4) 0.0247(3) Uani 1 1 d . . .
H17A H -0.1687 0.1344 0.6692 0.030 Uiso 1 1 calc R . .
H17B H 0.0555 0.0672 0.6858 0.030 Uiso 1 1 calc R . .
C18 C -0.0432(2) 0.28579(19) 0.71713(5) 0.0234(3) Uani 1 1 d . . .
H18A H -0.1380 0.3827 0.7107 0.028 Uiso 1 1 calc R . .
H18B H -0.1039 0.2213 0.7413 0.028 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
S1 0.02234(18) 0.02464(17) 0.02588(17) -0.00133(14) 0.00762(17) -0.00553(19)
N1 0.0193(7) 0.0183(6) 0.0209(6) -0.0010(5) 0.0012(5) -0.0010(6)
N2 0.0221(7) 0.0193(6) 0.0203(6) 0.0002(5) 0.0031(5) -0.0028(6)
N3 0.0255(7) 0.0309(7) 0.0201(7) 0.0023(5) 0.0049(5) -0.0089(6)
O1 0.0229(6) 0.0332(6) 0.0199(5) 0.0055(4) -0.0013(4) 0.0008(5)
C1 0.0198(8) 0.0145(6) 0.0226(7) -0.0032(6) 0.0039(6) -0.0009(6)
C2 0.0213(8) 0.0166(6) 0.0241(7) -0.0020(5) 0.0059(6) -0.0009(7)
C3 0.0221(8) 0.0157(6) 0.0243(7) -0.0045(6) 0.0068(6) -0.0030(7)
C4 0.0202(8) 0.0217(7) 0.0321(8) -0.0051(7) 0.0045(6) -0.0028(7)
C5 0.0214(8) 0.0219(7) 0.0247(7) -0.0035(6) -0.0012(6) 0.0002(7)
C6 0.0201(8) 0.0147(6) 0.0218(7) -0.0037(5) 0.0008(6) 0.0020(6)
C7 0.0199(7) 0.0157(6) 0.0209(7) -0.0026(5) 0.0005(6) 0.0012(6)
C8 0.0180(8) 0.0267(7) 0.0265(8) -0.0020(6) -0.0026(6) -0.0012(7)
C9 0.0227(9) 0.0299(8) 0.0221(8) -0.0002(6) -0.0052(6) 0.0024(7)
C10 0.0215(8) 0.0199(7) 0.0193(7) -0.0020(5) -0.0004(6) 0.0043(6)
C11 0.0176(8) 0.0202(6) 0.0214(6) -0.0023(5) -0.0001(6) 0.0021(7)
C12 0.0197(8) 0.0182(6) 0.0198(7) -0.0032(5) -0.0036(6) 0.0030(6)
C13 0.0235(8) 0.0328(9) 0.0216(8) 0.0012(6) -0.0001(6) -0.0050(8)
C14 0.0295(9) 0.0256(8) 0.0251(8) 0.0043(6) 0.0072(7) -0.0052(8)
C15 0.0297(9) 0.0244(8) 0.0234(8) 0.0053(6) 0.0106(7) 0.0023(7)
C16 0.0368(10) 0.0297(8) 0.0189(7) 0.0024(6) 0.0058(7) -0.0009(8)
C17 0.0277(9) 0.0244(7) 0.0221(7) 0.0034(6) 0.0015(7) -0.0049(8)
C18 0.0208(8) 0.0277(7) 0.0216(7) 0.0029(6) 0.0038(6) -0.0016(6)

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

# MOLECULAR GEOMETRY

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
S1 C2 1.7399(14) . ?
S1 C3 1.7780(17) . ?
N1 C1 1.3404(18) . ?
N1 C6 1.3579(19) . ?
N2 C3 1.3162(18) . ?
N2 C1 1.3856(19) . ?
N3 C3 1.339(2) . ?
N3 C14 1.4665(19) . ?
N3 C18 1.471(2) . ?
O1 C10 1.3672(18) . ?
O1 C13 1.4301(19) . ?
C1 C2 1.418(2) . ?
C2 C4 1.378(2) . ?
C4 C5 1.385(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.486(2) . ?
C7 C12 1.393(2) . ?
C7 C8 1.406(2) . ?
C8 C9 1.380(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.397(2) . ?
C11 C12 1.395(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.526(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.524(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.529(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.523(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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
C2 S1 C3 88.26(7) . . ?
C1 N1 C6 117.22(13) . . ?
C3 N2 C1 109.97(13) . . ?
C3 N3 C14 123.93(14) . . ?
C3 N3 C18 121.29(13) . . ?
C14 N3 C18 114.76(13) . . ?
C10 O1 C13 117.27(12) . . ?
N1 C1 N2 121.50(14) . . ?
N1 C1 C2 122.84(14) . . ?
N2 C1 C2 115.66(13) . . ?
C4 C2 C1 119.83(14) . . ?
C4 C2 S1 130.28(13) . . ?
C1 C2 S1 109.87(11) . . ?
N2 C3 N3 124.70(14) . . ?
N2 C3 S1 116.21(12) . . ?
N3 C3 S1 119.09(11) . . ?
C2 C4 C5 117.23(15) . . ?
C2 C4 H4 121.4 . . ?
C5 C4 H4 121.4 . . ?
C4 C5 C6 120.66(14) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
N1 C6 C5 122.16(14) . . ?
N1 C6 C7 116.37(13) . . ?
C5 C6 C7 121.46(13) . . ?
C12 C7 C8 117.19(14) . . ?
C12 C7 C6 121.20(13) . . ?
C8 C7 C6 121.59(14) . . ?
C9 C8 C7 121.18(15) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120.77(15) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
O1 C10 C9 115.52(14) . . ?
O1 C10 C11 125.02(15) . . ?
C9 C10 C11 119.45(14) . . ?
C12 C11 C10 119.09(15) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C7 C12 C11 122.28(14) . . ?
C7 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 110.34(13) . . ?
N3 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
N3 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 110.58(14) . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 C17 110.65(13) . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C16 110.96(12) . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
N3 C18 C17 109.58(13) . . ?
N3 C18 H18A 109.8 . . ?
C17 C18 H18A 109.8 . . ?
N3 C18 H18B 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?

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
C6 N1 C1 N2 178.05(13) . . . . ?
C6 N1 C1 C2 -1.1(2) . . . . ?
C3 N2 C1 N1 179.36(13) . . . . ?
C3 N2 C1 C2 -1.39(18) . . . . ?
N1 C1 C2 C4 2.9(2) . . . . ?
N2 C1 C2 C4 -176.33(13) . . . . ?
N1 C1 C2 S1 -178.78(11) . . . . ?
N2 C1 C2 S1 1.98(15) . . . . ?
C3 S1 C2 C4 176.60(15) . . . . ?
C3 S1 C2 C1 -1.47(10) . . . . ?
C1 N2 C3 N3 -179.47(14) . . . . ?
C1 N2 C3 S1 0.17(16) . . . . ?
C14 N3 C3 N2 176.89(14) . . . . ?
C18 N3 C3 N2 -1.3(2) . . . . ?
C14 N3 C3 S1 -2.7(2) . . . . ?
C18 N3 C3 S1 179.05(11) . . . . ?
C2 S1 C3 N2 0.80(12) . . . . ?
C2 S1 C3 N3 -179.55(13) . . . . ?
C1 C2 C4 C5 -2.2(2) . . . . ?
S1 C2 C4 C5 179.89(11) . . . . ?
C2 C4 C5 C6 0.0(2) . . . . ?
C1 N1 C6 C5 -1.2(2) . . . . ?
C1 N1 C6 C7 -179.96(12) . . . . ?
C4 C5 C6 N1 1.8(2) . . . . ?
C4 C5 C6 C7 -179.49(14) . . . . ?
N1 C6 C7 C12 -4.1(2) . . . . ?
C5 C6 C7 C12 177.13(14) . . . . ?
N1 C6 C7 C8 174.31(14) . . . . ?
C5 C6 C7 C8 -4.5(2) . . . . ?
C12 C7 C8 C9 1.7(2) . . . . ?
C6 C7 C8 C9 -176.76(14) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C13 O1 C10 C9 162.43(14) . . . . ?
C13 O1 C10 C11 -18.0(2) . . . . ?
C8 C9 C10 O1 178.45(14) . . . . ?
C8 C9 C10 C11 -1.1(2) . . . . ?
O1 C10 C11 C12 -178.19(13) . . . . ?
C9 C10 C11 C12 1.3(2) . . . . ?
C8 C7 C12 C11 -1.5(2) . . . . ?
C6 C7 C12 C11 176.98(13) . . . . ?
C10 C11 C12 C7 0.0(2) . . . . ?
C3 N3 C14 C15 124.64(17) . . . . ?
C18 N3 C14 C15 -57.03(18) . . . . ?
N3 C14 C15 C16 54.47(19) . . . . ?
C14 C15 C16 C17 -54.85(18) . . . . ?
C15 C16 C17 C18 55.54(18) . . . . ?
C3 N3 C18 C17 -124.54(15) . . . . ?
C14 N3 C18 C17 57.08(16) . . . . ?
C16 C17 C18 N3 -55.03(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.046