# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Peter Wipf'
_publ_contact_author_email       pwipf@pitt.edu
loop_
_publ_author_name
P.Wipf
'Liming Cao'
J.Maciejewski
S.Elzner
D.Amantini

data_liming1
_database_code_depnum_ccdc_archive 'CCDC 868588'
#TrackingRef '- 23a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 N3 O2'
_chemical_formula_weight         305.33
_chemical_absolute_configuration unk

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   4.9211(3)
_cell_length_b                   12.5759(8)
_cell_length_c                   23.0138(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1424.26(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9266
_exptl_absorpt_correction_T_max  0.9697
_exptl_absorpt_process_details   'Bruker Sadabs'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6323
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.01
_diffrn_reflns_theta_max         61.24
_reflns_number_total             1280
_reflns_number_gt                1186
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0780P)^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    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   0.1(6)
_refine_ls_number_reflns         1280
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0784
_refine_ls_wR_factor_ref         0.1722
_refine_ls_wR_factor_gt          0.1707
_refine_ls_goodness_of_fit_ref   1.784
_refine_ls_restrained_S_all      1.784
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0101(7) 1.0606(2) 0.87843(15) 0.0375(9) Uani 1 1 d . . .
N1 N 0.1825(7) 0.9401(2) 0.81536(16) 0.0230(8) Uani 1 1 d . . .
C1 C 0.4566(9) 0.9908(3) 0.73242(19) 0.0285(10) Uani 1 1 d . . .
H1A H 0.3049 0.9933 0.7042 0.034 Uiso 1 1 calc R . .
H1B H 0.6000 1.0403 0.7190 0.034 Uiso 1 1 calc R . .
O2 O 0.0562(6) 0.6583(2) 0.80096(14) 0.0311(8) Uani 1 1 d . . .
N2 N 0.3996(6) 0.8079(2) 0.75720(16) 0.0231(9) Uani 1 1 d . . .
C2 C 0.3560(10) 1.0246(3) 0.7920(2) 0.0286(11) Uani 1 1 d . . .
H2A H 0.5122 1.0369 0.8183 0.034 Uiso 1 1 calc R . .
H2B H 0.2515 1.0916 0.7889 0.034 Uiso 1 1 calc R . .
N3 N 0.5644(7) 0.8837(3) 0.73557(16) 0.0250(9) Uani 1 1 d . . .
C3 C 0.0115(9) 0.9689(3) 0.8601(2) 0.0260(10) Uani 1 1 d . . .
C4 C -0.1645(9) 0.8854(3) 0.8841(2) 0.0258(10) Uani 1 1 d . . .
C5 C -0.3529(9) 0.9138(4) 0.9275(2) 0.0314(11) Uani 1 1 d . . .
H5A H -0.3645 0.9853 0.9406 0.038 Uiso 1 1 calc R . .
C6 C -0.5206(9) 0.8369(4) 0.9507(2) 0.0346(11) Uani 1 1 d . . .
H6A H -0.6491 0.8563 0.9796 0.042 Uiso 1 1 calc R . .
C7 C -0.5054(9) 0.7320(4) 0.9327(2) 0.0306(11) Uani 1 1 d . . .
H7A H -0.6206 0.6798 0.9496 0.037 Uiso 1 1 calc R . .
C8 C -0.3203(9) 0.7035(3) 0.8898(2) 0.0270(10) Uani 1 1 d . . .
H8A H -0.3095 0.6317 0.8771 0.032 Uiso 1 1 calc R . .
C9 C -0.1511(9) 0.7799(3) 0.86552(19) 0.0228(10) Uani 1 1 d . . .
C10 C 0.0434(9) 0.7499(3) 0.81837(19) 0.0222(10) Uani 1 1 d . . .
C11 C 0.2141(8) 0.8356(3) 0.79565(18) 0.0210(10) Uani 1 1 d . . .
C12 C 0.7196(9) 0.8483(3) 0.68392(19) 0.0261(10) Uani 1 1 d . . .
H12A H 0.7847 0.7748 0.6905 0.031 Uiso 1 1 calc R . .
H12B H 0.8809 0.8945 0.6792 0.031 Uiso 1 1 calc R . .
C13 C 0.5965(9) 0.9317(4) 0.5878(2) 0.0293(11) Uani 1 1 d . . .
H13A H 0.7315 0.9842 0.5946 0.035 Uiso 1 1 calc R . .
C14 C 0.4399(10) 0.9342(3) 0.53675(19) 0.0315(11) Uani 1 1 d . . .
H14A H 0.4719 0.9879 0.5085 0.038 Uiso 1 1 calc R . .
C15 C 0.2418(10) 0.8601(3) 0.52749(19) 0.0292(11) Uani 1 1 d . . .
H15A H 0.1346 0.8633 0.4932 0.035 Uiso 1 1 calc R . .
C16 C 0.1956(10) 0.7796(3) 0.5680(2) 0.0297(11) Uani 1 1 d . . .
H16A H 0.0584 0.7277 0.5616 0.036 Uiso 1 1 calc R . .
C17 C 0.3554(9) 0.7767(3) 0.6182(2) 0.0263(10) Uani 1 1 d . . .
H17A H 0.3269 0.7219 0.6459 0.032 Uiso 1 1 calc R . .
C18 C 0.5519(8) 0.8513(3) 0.62817(18) 0.0245(10) 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
O1 0.053(2) 0.0250(17) 0.0341(19) -0.0097(14) -0.0019(16) 0.0037(16)
N1 0.0300(17) 0.0209(18) 0.0183(19) -0.0039(14) -0.0056(16) 0.0009(16)
C1 0.033(2) 0.028(2) 0.024(2) 0.0055(19) -0.0013(19) -0.005(2)
O2 0.0365(16) 0.0240(17) 0.0329(18) -0.0029(13) 0.0067(14) -0.0012(14)
N2 0.0219(16) 0.0278(19) 0.020(2) 0.0012(15) -0.0047(16) -0.0006(15)
C2 0.038(2) 0.022(2) 0.026(3) -0.0010(19) -0.007(2) -0.004(2)
N3 0.0290(18) 0.0253(18) 0.021(2) 0.0016(15) 0.0010(17) -0.0061(16)
C3 0.032(2) 0.025(2) 0.021(2) -0.0038(18) -0.0041(18) 0.006(2)
C4 0.027(2) 0.033(2) 0.018(2) -0.0039(19) -0.0044(17) 0.006(2)
C5 0.038(2) 0.039(3) 0.017(2) -0.007(2) -0.003(2) 0.010(2)
C6 0.032(2) 0.053(3) 0.019(2) 0.002(2) 0.0003(19) 0.012(3)
C7 0.027(2) 0.044(3) 0.020(2) 0.005(2) 0.0002(19) 0.001(2)
C8 0.028(2) 0.036(2) 0.017(2) 0.0002(19) -0.0023(19) 0.001(2)
C9 0.024(2) 0.028(2) 0.016(2) 0.0011(17) -0.0043(17) 0.0033(19)
C10 0.025(2) 0.025(2) 0.017(2) -0.0002(17) -0.0033(18) 0.0015(19)
C11 0.026(2) 0.019(2) 0.018(2) -0.0020(17) -0.0029(17) 0.0011(18)
C12 0.025(2) 0.033(2) 0.019(2) 0.0059(19) 0.0010(18) -0.0008(19)
C13 0.030(2) 0.032(2) 0.027(3) 0.0034(19) 0.0042(19) -0.001(2)
C14 0.043(2) 0.034(3) 0.018(2) 0.0066(18) 0.005(2) 0.002(2)
C15 0.037(2) 0.034(3) 0.017(2) 0.0019(18) 0.0004(18) 0.007(2)
C16 0.035(2) 0.031(2) 0.024(2) -0.0021(19) -0.001(2) -0.002(2)
C17 0.034(2) 0.025(2) 0.020(2) 0.0048(18) 0.0026(18) 0.002(2)
C18 0.0259(19) 0.027(2) 0.021(2) 0.0022(18) 0.0024(18) 0.0030(19)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.228(5) . ?
N1 C3 1.379(6) . ?
N1 C11 1.398(5) . ?
N1 C2 1.466(6) . ?
C1 N3 1.450(6) . ?
C1 C2 1.518(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
O2 C10 1.221(5) . ?
N2 C11 1.319(5) . ?
N2 N3 1.347(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N3 C12 1.482(5) . ?
C3 C4 1.469(6) . ?
C4 C9 1.395(6) . ?
C4 C5 1.408(6) . ?
C5 C6 1.380(7) . ?
C5 H5A 0.9500 . ?
C6 C7 1.385(7) . ?
C6 H6A 0.9500 . ?
C7 C8 1.391(7) . ?
C7 H7A 0.9500 . ?
C8 C9 1.389(6) . ?
C8 H8A 0.9500 . ?
C9 C10 1.495(6) . ?
C10 C11 1.463(6) . ?
C12 C18 1.526(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.391(6) . ?
C13 C14 1.405(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.366(7) . ?
C14 H14A 0.9500 . ?
C15 C16 1.395(6) . ?
C15 H15A 0.9500 . ?
C16 C17 1.398(7) . ?
C16 H16A 0.9500 . ?
C17 C18 1.366(6) . ?
C17 H17A 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
C3 N1 C11 123.9(4) . . ?
C3 N1 C2 116.0(3) . . ?
C11 N1 C2 119.9(4) . . ?
N3 C1 C2 109.5(3) . . ?
N3 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N3 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
C11 N2 N3 118.5(3) . . ?
N1 C2 C1 108.5(3) . . ?
N1 C2 H2A 110.0 . . ?
C1 C2 H2A 110.0 . . ?
N1 C2 H2B 110.0 . . ?
C1 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
N2 N3 C1 117.1(3) . . ?
N2 N3 C12 113.2(3) . . ?
C1 N3 C12 115.4(3) . . ?
O1 C3 N1 120.5(4) . . ?
O1 C3 C4 122.7(4) . . ?
N1 C3 C4 116.9(4) . . ?
C9 C4 C5 119.4(4) . . ?
C9 C4 C3 122.5(4) . . ?
C5 C4 C3 118.2(4) . . ?
C6 C5 C4 119.4(4) . . ?
C6 C5 H5A 120.3 . . ?
C4 C5 H5A 120.3 . . ?
C5 C6 C7 121.3(4) . . ?
C5 C6 H6A 119.3 . . ?
C7 C6 H6A 119.3 . . ?
C6 C7 C8 119.6(4) . . ?
C6 C7 H7A 120.2 . . ?
C8 C7 H7A 120.2 . . ?
C9 C8 C7 120.0(4) . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C8 C9 C4 120.4(4) . . ?
C8 C9 C10 120.1(4) . . ?
C4 C9 C10 119.5(4) . . ?
O2 C10 C11 123.2(4) . . ?
O2 C10 C9 120.6(4) . . ?
C11 C10 C9 116.2(4) . . ?
N2 C11 N1 122.9(4) . . ?
N2 C11 C10 116.3(4) . . ?
N1 C11 C10 120.8(4) . . ?
N3 C12 C18 112.8(3) . . ?
N3 C12 H12A 109.0 . . ?
C18 C12 H12A 109.0 . . ?
N3 C12 H12B 109.0 . . ?
C18 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C18 C13 C14 119.3(4) . . ?
C18 C13 H13A 120.4 . . ?
C14 C13 H13A 120.4 . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C14 C15 C16 120.5(4) . . ?
C14 C15 H15A 119.7 . . ?
C16 C15 H15A 119.7 . . ?
C15 C16 C17 118.6(4) . . ?
C15 C16 H16A 120.7 . . ?
C17 C16 H16A 120.7 . . ?
C18 C17 C16 121.3(4) . . ?
C18 C17 H17A 119.3 . . ?
C16 C17 H17A 119.3 . . ?
C17 C18 C13 119.9(4) . . ?
C17 C18 C12 120.5(4) . . ?
C13 C18 C12 119.7(4) . . ?

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
C3 N1 C2 C1 -161.4(4) . . . . ?
C11 N1 C2 C1 24.1(5) . . . . ?
N3 C1 C2 N1 -49.1(5) . . . . ?
C11 N2 N3 C1 -29.0(5) . . . . ?
C11 N2 N3 C12 -167.0(3) . . . . ?
C2 C1 N3 N2 54.7(5) . . . . ?
C2 C1 N3 C12 -168.2(4) . . . . ?
C11 N1 C3 O1 174.0(4) . . . . ?
C2 N1 C3 O1 -0.2(6) . . . . ?
C11 N1 C3 C4 -5.9(6) . . . . ?
C2 N1 C3 C4 179.9(4) . . . . ?
O1 C3 C4 C9 -176.2(4) . . . . ?
N1 C3 C4 C9 3.7(6) . . . . ?
O1 C3 C4 C5 3.9(7) . . . . ?
N1 C3 C4 C5 -176.2(4) . . . . ?
C9 C4 C5 C6 0.0(7) . . . . ?
C3 C4 C5 C6 180.0(4) . . . . ?
C4 C5 C6 C7 0.7(7) . . . . ?
C5 C6 C7 C8 -0.9(7) . . . . ?
C6 C7 C8 C9 0.4(7) . . . . ?
C7 C8 C9 C4 0.3(7) . . . . ?
C7 C8 C9 C10 -178.5(4) . . . . ?
C5 C4 C9 C8 -0.5(7) . . . . ?
C3 C4 C9 C8 179.5(4) . . . . ?
C5 C4 C9 C10 178.3(4) . . . . ?
C3 C4 C9 C10 -1.6(6) . . . . ?
C8 C9 C10 O2 -0.3(6) . . . . ?
C4 C9 C10 O2 -179.1(4) . . . . ?
C8 C9 C10 C11 -179.7(4) . . . . ?
C4 C9 C10 C11 1.4(6) . . . . ?
N3 N2 C11 N1 -0.6(6) . . . . ?
N3 N2 C11 C10 -179.1(3) . . . . ?
C3 N1 C11 N2 -172.4(4) . . . . ?
C2 N1 C11 N2 1.5(6) . . . . ?
C3 N1 C11 C10 6.0(6) . . . . ?
C2 N1 C11 C10 180.0(3) . . . . ?
O2 C10 C11 N2 -4.4(6) . . . . ?
C9 C10 C11 N2 175.1(3) . . . . ?
O2 C10 C11 N1 177.1(4) . . . . ?
C9 C10 C11 N1 -3.4(6) . . . . ?
N2 N3 C12 C18 79.8(4) . . . . ?
C1 N3 C12 C18 -59.0(5) . . . . ?
C18 C13 C14 C15 1.4(7) . . . . ?
C13 C14 C15 C16 -1.2(7) . . . . ?
C14 C15 C16 C17 0.2(7) . . . . ?
C15 C16 C17 C18 0.6(6) . . . . ?
C16 C17 C18 C13 -0.3(6) . . . . ?
C16 C17 C18 C12 178.6(4) . . . . ?
C14 C13 C18 C17 -0.7(6) . . . . ?
C14 C13 C18 C12 -179.6(4) . . . . ?
N3 C12 C18 C17 -73.9(5) . . . . ?
N3 C12 C18 C13 105.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        61.00
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.112

# Attachment '- 23b.cif'

data_liming4_0m
_database_code_depnum_ccdc_archive 'CCDC 868589'
#TrackingRef '- 23b.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N3 O2'
_chemical_formula_weight         306.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   17.193(4)
_cell_length_b                   4.8775(12)
_cell_length_c                   17.519(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.213(14)
_cell_angle_gamma                90.00
_cell_volume                     1435.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       chunk
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9811
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_process_details   'Bruker Sadabs'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6403
_diffrn_reflns_av_R_equivalents  0.2280
_diffrn_reflns_av_sigmaI/netI    0.1206
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         41.15
_reflns_number_total             933
_reflns_number_gt                439
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0790P)^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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0016(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         933
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1628
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_restrained_S_all      0.929
_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
N1 N 0.7822(7) -0.010(3) 0.5882(7) 0.049(3) Uani 1 1 d . . .
O1 O 0.7943(5) -0.3524(18) 0.5035(4) 0.062(3) Uani 1 1 d . . .
C1 C 0.9158(7) 0.103(2) 0.5947(6) 0.055(3) Uani 1 1 d . . .
H1A H 0.9076 0.2980 0.6067 0.066 Uiso 1 1 calc R . .
H1B H 0.9028 0.0815 0.5372 0.066 Uiso 1 1 calc R . .
N2 N 0.8609(7) -0.0706(18) 0.6294(6) 0.055(3) Uani 1 1 d . . .
C2 C 1.0009(8) 0.030(3) 0.6248(8) 0.048(3) Uani 1 1 d . . .
O2 O 0.6198(5) 0.4551(17) 0.5888(4) 0.061(3) Uani 1 1 d . . .
N3 N 0.7634(6) 0.3421(19) 0.6773(7) 0.051(3) Uani 1 1 d . . .
C3 C 1.0520(11) 0.171(2) 0.6843(8) 0.073(4) Uani 1 1 d . . .
H3A H 1.0311 0.3181 0.7094 0.087 Uiso 1 1 calc R . .
C4 C 1.1313(11) 0.108(5) 0.7080(9) 0.115(7) Uani 1 1 d . . .
H4A H 1.1645 0.2073 0.7488 0.138 Uiso 1 1 calc R . .
C5 C 1.1606(14) -0.099(5) 0.6719(16) 0.135(10) Uani 1 1 d . . .
H5A H 1.2159 -0.1378 0.6861 0.162 Uiso 1 1 calc R . .
C6 C 1.1130(14) -0.256(4) 0.6150(11) 0.111(7) Uani 1 1 d . . .
H6A H 1.1343 -0.4075 0.5922 0.133 Uiso 1 1 calc R . .
C7 C 1.0315(10) -0.184(3) 0.5914(7) 0.073(4) Uani 1 1 d . . .
H7A H 0.9978 -0.2877 0.5516 0.088 Uiso 1 1 calc R . .
C8 C 0.8656(6) -0.015(3) 0.7123(6) 0.057(4) Uani 1 1 d . . .
H8A H 0.9212 -0.0422 0.7410 0.069 Uiso 1 1 calc R . .
H8B H 0.8319 -0.1492 0.7328 0.069 Uiso 1 1 calc R . .
C9 C 0.8394(7) 0.271(2) 0.7281(6) 0.053(3) Uani 1 1 d . . .
H9A H 0.8345 0.2848 0.7833 0.064 Uiso 1 1 calc R . .
H9B H 0.8803 0.4043 0.7199 0.064 Uiso 1 1 calc R . .
C10 C 0.7408(7) 0.208(3) 0.6168(9) 0.050(4) Uani 1 1 d . . .
C11 C 0.7544(8) -0.162(3) 0.5213(9) 0.051(4) Uani 1 1 d . . .
C12 C 0.6750(9) -0.079(3) 0.4753(8) 0.050(4) Uani 1 1 d . . .
C13 C 0.6499(8) -0.225(2) 0.4045(9) 0.054(3) Uani 1 1 d . . .
H13A H 0.6904 -0.1950 0.3727 0.064 Uiso 1 1 calc R . .
H13B H 0.6510 -0.4223 0.4176 0.064 Uiso 1 1 calc R . .
C14 C 0.5749(9) -0.168(3) 0.3565(7) 0.074(4) Uani 1 1 d . . .
H14A H 0.5567 -0.2672 0.3095 0.088 Uiso 1 1 calc R . .
C15 C 0.5285(7) 0.035(3) 0.3793(9) 0.063(4) Uani 1 1 d . . .
H15A H 0.4778 0.0750 0.3475 0.076 Uiso 1 1 calc R . .
C16 C 0.5543(8) 0.177(2) 0.4467(9) 0.051(3) Uani 1 1 d . . .
H16A H 0.5214 0.3159 0.4612 0.061 Uiso 1 1 calc R . .
C17 C 0.6292(9) 0.122(3) 0.4953(8) 0.039(3) Uani 1 1 d . . .
C18 C 0.6574(8) 0.269(3) 0.5673(9) 0.057(4) 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
N1 0.046(9) 0.052(8) 0.045(9) 0.006(7) 0.002(8) 0.010(8)
O1 0.070(7) 0.062(7) 0.054(6) -0.003(5) 0.009(5) 0.007(5)
C1 0.057(10) 0.055(9) 0.049(8) 0.006(6) 0.002(8) 0.007(8)
N2 0.045(8) 0.068(8) 0.043(8) 0.001(6) -0.012(7) 0.000(7)
C2 0.039(10) 0.050(10) 0.057(10) 0.027(8) 0.015(9) 0.005(9)
O2 0.062(6) 0.073(7) 0.047(6) -0.012(5) 0.006(4) 0.014(5)
N3 0.047(8) 0.077(8) 0.024(7) -0.003(6) -0.005(6) 0.002(6)
C3 0.074(13) 0.086(10) 0.056(10) -0.001(9) 0.007(9) -0.027(10)
C4 0.033(13) 0.21(2) 0.079(14) 0.077(14) -0.038(10) -0.040(11)
C5 0.086(19) 0.17(2) 0.17(3) 0.090(19) 0.075(17) 0.064(17)
C6 0.13(2) 0.130(17) 0.097(15) 0.063(13) 0.070(13) 0.018(16)
C7 0.051(13) 0.091(12) 0.081(11) 0.029(9) 0.022(9) 0.039(9)
C8 0.052(9) 0.084(11) 0.028(9) 0.003(7) -0.011(6) 0.003(8)
C9 0.053(9) 0.064(10) 0.039(8) 0.004(7) 0.002(8) 0.000(7)
C10 0.028(11) 0.069(13) 0.046(11) 0.022(10) -0.007(11) 0.002(9)
C11 0.054(14) 0.059(12) 0.031(11) 0.017(11) -0.010(9) -0.007(10)
C12 0.067(12) 0.055(11) 0.020(10) -0.002(8) -0.006(11) -0.007(11)
C13 0.050(11) 0.053(9) 0.065(11) 0.031(10) 0.027(8) -0.004(8)
C14 0.053(11) 0.091(12) 0.067(10) -0.006(9) -0.009(10) 0.009(9)
C15 0.059(10) 0.067(10) 0.062(12) -0.006(9) 0.010(9) -0.006(10)
C16 0.041(10) 0.070(10) 0.043(10) 0.006(9) 0.010(7) 0.010(8)
C17 0.047(11) 0.036(9) 0.039(12) -0.001(8) 0.021(11) 0.014(9)
C18 0.075(16) 0.056(11) 0.047(11) -0.015(10) 0.029(10) -0.002(10)

_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
N1 C11 1.384(13) . ?
N1 N2 1.423(10) . ?
N1 C10 1.429(14) . ?
O1 C11 1.232(13) . ?
C1 N2 1.490(11) . ?
C1 C2 1.490(13) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C8 1.463(11) . ?
C2 C7 1.358(14) . ?
C2 C3 1.394(14) . ?
O2 C18 1.219(12) . ?
N3 C10 1.237(13) . ?
N3 C9 1.457(12) . ?
C3 C4 1.374(16) . ?
C3 H3A 0.9500 . ?
C4 C5 1.34(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.38(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.419(18) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 C9 1.512(12) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C18 1.540(15) . ?
C11 C12 1.488(16) . ?
C12 C17 1.347(13) . ?
C12 C13 1.415(13) . ?
C13 C14 1.410(12) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.381(13) . ?
C14 H14A 0.9500 . ?
C15 C16 1.361(12) . ?
C15 H15A 0.9500 . ?
C16 C17 1.412(12) . ?
C16 H16A 0.9500 . ?
C17 C18 1.443(15) . ?

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
C11 N1 N2 116.1(12) . . ?
C11 N1 C10 126.0(12) . . ?
N2 N1 C10 117.8(11) . . ?
N2 C1 C2 112.2(9) . . ?
N2 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
N2 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N1 N2 C8 108.2(9) . . ?
N1 N2 C1 107.0(9) . . ?
C8 N2 C1 113.2(8) . . ?
C7 C2 C3 117.6(12) . . ?
C7 C2 C1 118.2(14) . . ?
C3 C2 C1 124.2(15) . . ?
C10 N3 C9 118.5(10) . . ?
C4 C3 C2 122.8(13) . . ?
C4 C3 H3A 118.6 . . ?
C2 C3 H3A 118.6 . . ?
C5 C4 C3 118.4(18) . . ?
C5 C4 H4A 120.8 . . ?
C3 C4 H4A 120.8 . . ?
C4 C5 C6 122(2) . . ?
C4 C5 H5A 118.9 . . ?
C6 C5 H5A 118.9 . . ?
C5 C6 C7 118(2) . . ?
C5 C6 H6A 120.9 . . ?
C7 C6 H6A 120.9 . . ?
C2 C7 C6 120.8(15) . . ?
C2 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
N2 C8 C9 113.4(8) . . ?
N2 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
N2 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
N3 C9 C8 111.8(8) . . ?
N3 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
N3 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
N3 C10 N1 127.2(11) . . ?
N3 C10 C18 117.8(15) . . ?
N1 C10 C18 114.8(14) . . ?
O1 C11 N1 120.4(13) . . ?
O1 C11 C12 124.4(16) . . ?
N1 C11 C12 115.2(14) . . ?
C17 C12 C13 120.4(13) . . ?
C17 C12 C11 125.3(14) . . ?
C13 C12 C11 114.3(18) . . ?
C14 C13 C12 119.6(11) . . ?
C14 C13 H13A 107.4 . . ?
C12 C13 H13A 107.4 . . ?
C14 C13 H13B 107.4 . . ?
C12 C13 H13B 107.4 . . ?
H13A C13 H13B 106.9 . . ?
C15 C14 C13 118.7(12) . . ?
C15 C14 H14A 120.7 . . ?
C13 C14 H14A 120.7 . . ?
C16 C15 C14 120.9(11) . . ?
C16 C15 H15A 119.5 . . ?
C14 C15 H15A 119.5 . . ?
C15 C16 C17 120.9(11) . . ?
C15 C16 H16A 119.5 . . ?
C17 C16 H16A 119.6 . . ?
C12 C17 C16 119.4(13) . . ?
C12 C17 C18 118.8(13) . . ?
C16 C17 C18 121.7(16) . . ?
O2 C18 C17 122.7(14) . . ?
O2 C18 C10 117.4(14) . . ?
C17 C18 C10 119.7(14) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        41.15
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.046

# Attachment '- 28.cif'

data_liming4b_0m
_database_code_depnum_ccdc_archive 'CCDC 868590'
#TrackingRef '- 28.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 N3 O2'
_chemical_formula_weight         215.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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                   4.9819(5)
_cell_length_b                   6.5576(6)
_cell_length_c                   28.039(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     916.01(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1331
_cell_measurement_theta_min      3.152
_cell_measurement_theta_max      58.106

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8890
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_process_details   'Bruker Sadabs'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4855
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         58.83
_reflns_number_total             823
_reflns_number_gt                702
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0623P)^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     SHELXL
_refine_ls_extinction_coef       0.0040(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         823
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0933
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9803(5) 0.7587(3) 0.17288(8) 0.0302(7) Uani 1 1 d . . .
N1 N 1.4702(6) 0.7061(4) 0.08004(9) 0.0211(7) Uani 1 1 d . . .
C1 C 1.1671(7) 0.6900(5) 0.15019(12) 0.0218(8) Uani 1 1 d . . .
O2 O 1.8126(5) 0.4850(4) 0.07027(8) 0.0264(7) Uani 1 1 d . . .
C2 C 1.3120(7) 0.5024(5) 0.16471(11) 0.0209(8) Uani 1 1 d . . .
N2 N 1.5305(6) 0.7922(4) 0.03427(10) 0.0227(7) Uani 1 1 d . . .
H2N H 1.710(9) 0.744(6) 0.0257(13) 0.047(12) Uiso 1 1 d . . .
N3 N 1.1443(6) 0.9630(4) 0.09355(10) 0.0243(7) Uani 1 1 d . . .
C3 C 1.2307(7) 0.3954(5) 0.20508(12) 0.0232(9) Uani 1 1 d . . .
H3A H 1.0837 0.4432 0.2236 0.028 Uiso 1 1 calc R . .
C4 C 1.3644(7) 0.2194(5) 0.21825(12) 0.0266(9) Uani 1 1 d . . .
H4A H 1.3078 0.1451 0.2455 0.032 Uiso 1 1 calc R . .
C5 C 1.5808(7) 0.1514(5) 0.19159(12) 0.0253(9) Uani 1 1 d . . .
H5A H 1.6722 0.0305 0.2008 0.030 Uiso 1 1 calc R . .
C6 C 1.6651(7) 0.2579(5) 0.15168(11) 0.0228(9) Uani 1 1 d . . .
H6A H 1.8143 0.2108 0.1337 0.027 Uiso 1 1 calc R . .
C7 C 1.5302(7) 0.4343(5) 0.13807(11) 0.0196(8) Uani 1 1 d . . .
C8 C 1.6205(7) 0.5407(5) 0.09433(12) 0.0217(9) Uani 1 1 d . . .
C9 C 1.5262(7) 1.0149(5) 0.03805(12) 0.0237(8) Uani 1 1 d . . .
H9A H 1.5735 1.0776 0.0070 0.028 Uiso 1 1 calc R . .
H9B H 1.6572 1.0614 0.0623 0.028 Uiso 1 1 calc R . .
C10 C 1.2447(7) 1.0752(5) 0.05247(12) 0.0240(9) Uani 1 1 d . . .
H10A H 1.2422 1.2228 0.0599 0.029 Uiso 1 1 calc R . .
H10C H 1.1225 1.0522 0.0252 0.029 Uiso 1 1 calc R . .
C11 C 1.2596(7) 0.7973(5) 0.10543(11) 0.0202(8) 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
O1 0.0300(14) 0.0252(14) 0.0354(14) 0.0000(12) 0.0103(12) 0.0077(14)
N1 0.0243(15) 0.0165(14) 0.0226(15) 0.0017(13) 0.0014(13) 0.0015(14)
C1 0.0224(19) 0.0211(19) 0.0220(18) -0.0071(17) -0.0014(16) -0.0032(16)
O2 0.0265(14) 0.0200(13) 0.0326(14) -0.0006(12) 0.0061(12) 0.0051(12)
C2 0.0221(18) 0.0188(18) 0.0220(18) -0.0045(18) -0.0003(15) -0.0004(17)
N2 0.0263(15) 0.0204(15) 0.0215(15) 0.0012(14) 0.0040(14) 0.0022(15)
N3 0.0253(16) 0.0194(16) 0.0281(16) -0.0017(14) -0.0001(13) 0.0021(15)
C3 0.0207(17) 0.0229(18) 0.026(2) -0.0030(17) 0.0032(16) -0.0007(17)
C4 0.029(2) 0.0235(19) 0.0272(19) 0.0005(18) 0.0008(16) -0.0019(18)
C5 0.0281(18) 0.0206(18) 0.027(2) 0.0009(17) -0.0024(16) -0.0006(17)
C6 0.0237(18) 0.024(2) 0.0209(18) -0.0042(16) 0.0018(15) 0.0022(17)
C7 0.0216(17) 0.0157(17) 0.0214(18) -0.0019(14) 0.0012(15) -0.0022(16)
C8 0.0208(18) 0.0159(18) 0.0284(19) -0.0043(17) -0.0029(17) 0.0003(16)
C9 0.0297(18) 0.0156(17) 0.0259(17) 0.0008(16) -0.0031(17) -0.0025(18)
C10 0.032(2) 0.0146(17) 0.026(2) 0.0009(16) 0.0002(17) 0.0020(18)
C11 0.0203(17) 0.0187(18) 0.0215(17) -0.0055(16) -0.0008(14) -0.0014(17)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.214(4) . ?
N1 C8 1.378(4) . ?
N1 C11 1.402(4) . ?
N1 N2 1.434(4) . ?
C1 C2 1.483(5) . ?
C1 C11 1.511(5) . ?
O2 C8 1.227(4) . ?
C2 C7 1.393(5) . ?
C2 C3 1.392(5) . ?
N2 C9 1.465(4) . ?
N2 H2N 0.98(4) . ?
N3 C11 1.273(4) . ?
N3 C10 1.456(4) . ?
C3 C4 1.383(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.386(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.384(5) . ?
C5 H5A 0.9500 . ?
C6 C7 1.391(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.481(5) . ?
C9 C10 1.512(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10C 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
C8 N1 C11 126.5(3) . . ?
C8 N1 N2 117.2(3) . . ?
C11 N1 N2 116.3(3) . . ?
O1 C1 C2 122.5(3) . . ?
O1 C1 C11 119.8(3) . . ?
C2 C1 C11 117.8(3) . . ?
C7 C2 C3 120.1(3) . . ?
C7 C2 C1 119.9(3) . . ?
C3 C2 C1 120.0(3) . . ?
N1 N2 C9 109.0(3) . . ?
N1 N2 H2N 107(2) . . ?
C9 N2 H2N 111(2) . . ?
C11 N3 C10 118.9(3) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
C5 C6 C7 119.6(3) . . ?
C5 C6 H6A 120.2 . . ?
C7 C6 H6A 120.2 . . ?
C6 C7 C2 119.8(3) . . ?
C6 C7 C8 118.2(3) . . ?
C2 C7 C8 122.0(3) . . ?
O2 C8 N1 119.9(3) . . ?
O2 C8 C7 123.5(3) . . ?
N1 C8 C7 116.5(3) . . ?
N2 C9 C10 107.1(3) . . ?
N2 C9 H9A 110.3 . . ?
C10 C9 H9A 110.3 . . ?
N2 C9 H9B 110.3 . . ?
C10 C9 H9B 110.3 . . ?
H9A C9 H9B 108.6 . . ?
N3 C10 C9 113.5(3) . . ?
N3 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
N3 C10 H10C 108.9 . . ?
C9 C10 H10C 108.9 . . ?
H10A C10 H10C 107.7 . . ?
N3 C11 N1 124.6(3) . . ?
N3 C11 C1 118.5(3) . . ?
N1 C11 C1 116.9(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N N2 0.98(4) 2.33(4) 3.194(3) 147(3) 4_565

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        58.83
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.047