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


data_global

_journal_coden_Cambridge         177

_publ_requested_journal          'Organic & Biomolecular Chemistry'

loop_
_publ_author_name
'McNab, H.'

_publ_contact_author_name        H.McNab
_publ_contact_author_address     
;
West Mains Road

EDINBURGH
EH9 3JJ
;

_publ_contact_author_email       h.mcnab@ed.ac.uk

data_agmn02
_database_code_depnum_ccdc_archive 'CCDC 776464'
#TrackingRef '- Agmn02.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H8 N4 O'
_chemical_formula_sum            'C11 H8 N4 O'
_chemical_formula_weight         212.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.6400(4)
_cell_length_b                   5.6225(2)
_cell_length_c                   17.8376(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.381(2)
_cell_angle_gamma                90.00
_cell_volume                     950.99(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2445
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      26.14

_exptl_crystal_description       block
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.43
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6305
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         28.58
_reflns_number_total             2259
_reflns_number_gt                1913
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
912_ALERT_3_B Missing FCF Reflections Above STH/L=0.6 ........ 155
911_ALERT_3_C Missing FCF Refl. Between TH(Min) & STH/L=0.6 .. 5

Resolution & Completeness Statistics (Cumulative)
#===============================================================================
Theta sin(th)/Lambda Complete Expected Measured Missing
#-------------------------------------------------------------------------------
20.82 0.500 0.999 1000 999 1
23.01 0.550 0.999 1326 1325 1
25.24 0.600 0.997 1728 1723 5
#----------------------------------------------------------- ACTA Min. Res. ----
27.51 0.650 0.985 2199 2166 33
29.84 0.700 0.934 2419 2259 160

The data is 99.7% complete to 0.6 A.

063_ALERT_3_B Crystal Probably too Large for Beam Size ....... 1.00 mm

031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.50 Sigma
061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.81
062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96
125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?

Noted; no action taken

;

_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^)+(0.0596P)^2^+0.3977P] 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     SHELXL
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2259
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.41693(18) 1.2854(3) 0.06752(11) 0.0363(4) Uani 1 1 d . . .
H1A H 0.4581 1.4241 0.0490 0.054 Uiso 1 1 calc R . .
H1B H 0.4401 1.1478 0.0404 0.054 Uiso 1 1 calc R . .
H1C H 0.4532 1.2661 0.1209 0.054 Uiso 1 1 calc R . .
C2 C 0.25990(15) 1.3137(3) 0.05538(9) 0.0225(3) Uani 1 1 d . . .
O2 O 0.20099(11) 1.4806(2) 0.01994(6) 0.0286(3) Uani 1 1 d . . .
C3 C 0.17410(15) 1.1335(2) 0.08927(8) 0.0194(3) Uani 1 1 d . . .
C4 C 0.03194(15) 1.1619(3) 0.08102(8) 0.0204(3) Uani 1 1 d . . .
H4 H -0.0097 1.2914 0.0532 0.024 Uiso 1 1 calc R . .
C5 C -0.05628(15) 1.0004(3) 0.11341(8) 0.0196(3) Uani 1 1 d . . .
C6 C -0.20328(15) 1.0317(3) 0.10477(9) 0.0245(3) Uani 1 1 d . . .
H6 H -0.2463 1.1606 0.0772 0.029 Uiso 1 1 calc R . .
C7 C -0.28352(15) 0.8719(3) 0.13696(9) 0.0264(4) Uani 1 1 d . . .
H7 H -0.3805 0.8936 0.1310 0.032 Uiso 1 1 calc R . .
C8 C -0.22043(16) 0.6775(3) 0.17847(9) 0.0268(4) Uani 1 1 d . . .
H8 H -0.2763 0.5706 0.1995 0.032 Uiso 1 1 calc R . .
C9 C -0.07665(16) 0.6411(3) 0.18881(9) 0.0231(3) Uani 1 1 d . . .
H9 H -0.0347 0.5124 0.2169 0.028 Uiso 1 1 calc R . .
C10 C 0.00387(14) 0.8035(3) 0.15584(8) 0.0188(3) Uani 1 1 d . . .
N11 N 0.14981(12) 0.7820(2) 0.16338(7) 0.0186(3) Uani 1 1 d . . .
N12 N 0.23015(13) 0.6100(2) 0.20313(7) 0.0229(3) Uani 1 1 d . . .
N13 N 0.35905(13) 0.6575(2) 0.19554(7) 0.0246(3) Uani 1 1 d . . .
N14 N 0.36670(13) 0.8530(2) 0.15227(7) 0.0221(3) Uani 1 1 d . . .
C15 C 0.23515(14) 0.9313(3) 0.13260(8) 0.0188(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0247(8) 0.0376(9) 0.0497(11) 0.0163(8) 0.0152(7) 0.0023(7)
C2 0.0231(7) 0.0229(7) 0.0224(7) 0.0025(6) 0.0068(6) 0.0010(6)
O2 0.0279(6) 0.0269(6) 0.0309(6) 0.0085(5) 0.0050(5) 0.0014(4)
C3 0.0209(7) 0.0191(7) 0.0184(7) -0.0010(5) 0.0043(5) 0.0012(5)
C4 0.0214(7) 0.0195(7) 0.0200(7) 0.0014(5) 0.0032(5) 0.0024(5)
C5 0.0189(7) 0.0210(7) 0.0188(7) -0.0020(5) 0.0035(5) 0.0008(5)
C6 0.0204(7) 0.0269(8) 0.0259(8) 0.0002(6) 0.0029(6) 0.0041(6)
C7 0.0168(7) 0.0338(8) 0.0288(8) -0.0020(6) 0.0051(6) 0.0015(6)
C8 0.0230(7) 0.0314(8) 0.0270(8) 0.0010(7) 0.0070(6) -0.0054(6)
C9 0.0226(7) 0.0239(7) 0.0226(7) 0.0030(6) 0.0036(6) 0.0000(6)
C10 0.0166(7) 0.0212(7) 0.0183(7) -0.0028(5) 0.0027(5) -0.0003(5)
N11 0.0175(6) 0.0183(6) 0.0195(6) 0.0007(5) 0.0021(5) 0.0012(4)
N12 0.0209(6) 0.0223(6) 0.0241(7) 0.0039(5) 0.0005(5) 0.0028(5)
N13 0.0209(6) 0.0249(7) 0.0274(7) 0.0032(5) 0.0028(5) 0.0021(5)
N14 0.0189(6) 0.0230(6) 0.0241(6) 0.0024(5) 0.0031(5) 0.0031(5)
C15 0.0181(7) 0.0205(7) 0.0182(7) -0.0025(5) 0.0047(5) 0.0000(5)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.498(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O2 1.2137(18) . ?
C2 C3 1.502(2) . ?
C3 C4 1.361(2) . ?
C3 C15 1.4395(19) . ?
C4 C5 1.435(2) . ?
C4 H4 0.9300 . ?
C5 C10 1.406(2) . ?
C5 C6 1.409(2) . ?
C6 C7 1.377(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.397(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.395(2) . ?
C9 H9 0.9300 . ?
C10 N11 1.3942(17) . ?
N11 N12 1.3564(16) . ?
N11 C15 1.3584(18) . ?
N12 N13 1.3016(17) . ?
N13 N14 1.3527(18) . ?
N14 C15 1.3284(18) . ?

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 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 C1 121.54(14) . . ?
O2 C2 C3 119.42(13) . . ?
C1 C2 C3 119.03(13) . . ?
C4 C3 C15 117.21(13) . . ?
C4 C3 C2 119.59(13) . . ?
C15 C3 C2 123.18(12) . . ?
C3 C4 C5 122.70(13) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.6 . . ?
C10 C5 C6 117.79(13) . . ?
C10 C5 C4 119.89(13) . . ?
C6 C5 C4 122.32(13) . . ?
C7 C6 C5 120.19(14) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.54(14) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 121.17(14) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 117.93(14) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?
N11 C10 C9 122.08(13) . . ?
N11 C10 C5 115.54(12) . . ?
C9 C10 C5 122.38(13) . . ?
N12 N11 C15 108.74(11) . . ?
N12 N11 C10 125.69(12) . . ?
C15 N11 C10 125.57(12) . . ?
N13 N12 N11 105.39(11) . . ?
N12 N13 N14 112.15(12) . . ?
C15 N14 N13 105.81(12) . . ?
N14 C15 N11 107.90(12) . . ?
N14 C15 C3 133.00(13) . . ?
N11 C15 C3 119.08(12) . . ?

_diffrn_measured_fraction_theta_max 0.934
_diffrn_reflns_theta_full        28.58
_diffrn_measured_fraction_theta_full 0.934
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.058