# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_oxam
_database_code_depnum_ccdc_archive 'CCDC 1420804'
_audit_update_record             
;
2015-08-27 deposited with the CCDC.
2016-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 N3 O2'
_chemical_formula_sum            'C8 H7 N3 O2'
_chemical_formula_weight         177.17

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7205(15)
_cell_length_b                   7.824(2)
_cell_length_c                   9.811(3)
_cell_angle_alpha                72.891(4)
_cell_angle_beta                 85.142(4)
_cell_angle_gamma                74.695(4)
_cell_volume                     404.79(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             184.0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3825
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         24.98
_reflns_number_total             1419
_reflns_number_gt                1071
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0983P)²+0.0077P] where P=(Fo²+2Fc²)/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_number_reflns         1419
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1581
_refine_ls_wR_factor_gt          0.1481
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.008
_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 1.1699(3) 0.58273(19) 0.10492(16) 0.0468(5) Uani 1 1 d . . .
N2 N 0.7828(3) 0.7322(3) 0.11034(19) 0.0479(6) Uani 1 1 d . . .
O2 O 1.1959(3) 0.3702(2) 0.32313(18) 0.0623(6) Uani 1 1 d . . .
N3 N 0.8442(3) 0.5905(3) 0.2345(2) 0.0460(5) Uani 1 1 d . . .
C4 C 1.0240(4) 0.8392(3) -0.1028(2) 0.0420(6) Uani 1 1 d . . .
C5 C 0.8390(4) 0.9867(3) -0.1728(3) 0.0507(6) Uani 1 1 d . . .
H5 H 0.6890 1.0073 -0.1275 0.061 Uiso 1 1 calc R . .
C2 C 1.2751(5) 0.9253(3) -0.3023(3) 0.0571(7) Uani 1 1 d . . .
H2 H 1.4235 0.9089 -0.3497 0.069 Uiso 1 1 calc R . .
C7 C 1.0789(4) 0.4987(3) 0.2350(3) 0.0461(6) Uani 1 1 d . . .
C3 C 1.2469(4) 0.8103(3) -0.1704(3) 0.0522(7) Uani 1 1 d . . .
H3 H 1.3758 0.7141 -0.1268 0.063 Uiso 1 1 calc R . .
C6 C 0.9810(4) 0.7226(3) 0.0371(2) 0.0414(6) Uani 1 1 d . . .
N1 N 0.8646(4) 1.0992(3) -0.3003(2) 0.0586(6) Uani 1 1 d . . .
C1 C 1.0800(5) 1.0657(3) -0.3639(3) 0.0567(7) Uani 1 1 d . . .
H1 H 1.0997 1.1413 -0.4548 0.068 Uiso 1 1 calc R . .
C8 C 0.6732(4) 0.5568(4) 0.3506(3) 0.0583(7) Uani 1 1 d . . .
H8A H 0.7593 0.4998 0.4389 0.087 Uiso 1 1 calc R . .
H8B H 0.5831 0.4764 0.3355 0.087 Uiso 1 1 calc R . .
H8C H 0.5638 0.6719 0.3543 0.087 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0308(9) 0.0484(10) 0.0512(10) -0.0058(8) -0.0011(7) -0.0023(7)
N2 0.0349(11) 0.0532(12) 0.0507(12) -0.0098(10) -0.0030(9) -0.0073(9)
O2 0.0423(10) 0.0618(11) 0.0633(12) 0.0039(9) -0.0061(9) -0.0024(9)
N3 0.0301(10) 0.0512(11) 0.0501(11) -0.0072(9) -0.0003(8) -0.0071(8)
C4 0.0392(13) 0.0436(13) 0.0453(13) -0.0156(11) -0.0038(10) -0.0094(10)
C5 0.0366(13) 0.0562(15) 0.0537(15) -0.0130(13) -0.0021(10) -0.0047(11)
C2 0.0451(15) 0.0645(16) 0.0546(16) -0.0113(13) 0.0057(11) -0.0095(13)
C7 0.0352(13) 0.0468(13) 0.0531(14) -0.0092(11) -0.0019(10) -0.0101(11)
C3 0.0385(13) 0.0507(14) 0.0586(16) -0.0108(12) -0.0025(11) -0.0009(10)
C6 0.0329(12) 0.0437(13) 0.0467(13) -0.0143(11) -0.0065(10) -0.0044(10)
N1 0.0492(13) 0.0620(13) 0.0520(13) -0.0038(11) -0.0076(10) -0.0042(10)
C1 0.0618(18) 0.0591(16) 0.0471(15) -0.0097(12) 0.0004(12) -0.0178(14)
C8 0.0410(14) 0.0682(17) 0.0587(16) -0.0085(13) 0.0086(11) -0.0154(12)

_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 C6 1.370(2) . ?
O1 C7 1.381(3) . ?
N2 C6 1.287(3) . ?
N2 N3 1.382(3) . ?
O2 C7 1.199(3) . ?
N3 C7 1.345(3) . ?
N3 C8 1.447(3) . ?
C4 C3 1.382(3) . ?
C4 C5 1.391(3) . ?
C4 C6 1.450(3) . ?
C5 N1 1.323(3) . ?
C5 H5 0.9300 . ?
C2 C3 1.366(3) . ?
C2 C1 1.376(3) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
N1 C1 1.331(3) . ?
C1 H1 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
C6 O1 C7 105.87(17) . . ?
C6 N2 N3 103.98(18) . . ?
C7 N3 N2 111.91(19) . . ?
C7 N3 C8 125.8(2) . . ?
N2 N3 C8 122.19(19) . . ?
C3 C4 C5 117.8(2) . . ?
C3 C4 C6 122.0(2) . . ?
C5 C4 C6 120.2(2) . . ?
N1 C5 C4 123.6(2) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
O2 C7 N3 130.9(2) . . ?
O2 C7 O1 124.1(2) . . ?
N3 C7 O1 105.01(19) . . ?
C2 C3 C4 119.0(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
N2 C6 O1 113.21(19) . . ?
N2 C6 C4 128.3(2) . . ?
O1 C6 C4 118.5(2) . . ?
C5 N1 C1 117.1(2) . . ?
N1 C1 C2 123.5(2) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
C6 N2 N3 C7 0.6(2) . . . . ?
C6 N2 N3 C8 177.48(19) . . . . ?
C3 C4 C5 N1 0.5(4) . . . . ?
C6 C4 C5 N1 179.9(2) . . . . ?
N2 N3 C7 O2 179.7(2) . . . . ?
C8 N3 C7 O2 3.0(4) . . . . ?
N2 N3 C7 O1 -1.2(2) . . . . ?
C8 N3 C7 O1 -177.9(2) . . . . ?
C6 O1 C7 O2 -179.6(2) . . . . ?
C6 O1 C7 N3 1.2(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C5 C4 C3 C2 -0.7(3) . . . . ?
C6 C4 C3 C2 179.9(2) . . . . ?
N3 N2 C6 O1 0.2(2) . . . . ?
N3 N2 C6 C4 -179.4(2) . . . . ?
C7 O1 C6 N2 -0.9(2) . . . . ?
C7 O1 C6 C4 178.76(17) . . . . ?
C3 C4 C6 N2 -178.7(2) . . . . ?
C5 C4 C6 N2 1.9(3) . . . . ?
C3 C4 C6 O1 1.7(3) . . . . ?
C5 C4 C6 O1 -177.69(18) . . . . ?
C4 C5 N1 C1 0.8(3) . . . . ?
C5 N1 C1 C2 -1.9(4) . . . . ?
C3 C2 C1 N1 1.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.053
_exptl_crystal_recrystallization_method 
'By slow evaporation CDCl3 solvent slow evaporation'
