# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1034842'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 N3 O2'
_chemical_formula_weight         227.22

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           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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'
'-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                   11.5359(11)
_cell_length_b                   15.7377(15)
_cell_length_c                   23.975(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4352.6(7)
_cell_formula_units_Z            16
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    323
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      26.21

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  'Bruker APEX II Smart CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31955
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         26.21
_reflns_number_total             4367
_reflns_number_gt                3031
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0763P)²+1.1946P] where P=(Fo²+2Fc²)/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         4367
_refine_ls_number_parameters     323
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1583
_refine_ls_wR_factor_gt          0.1369
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.091
_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 0.61385(18) -0.00716(13) 0.71340(9) 0.0514(5) Uani 1 1 d . . .
C2 C 0.69735(19) -0.05244(14) 0.74377(10) 0.0589(6) Uani 1 1 d . . .
H2 H 0.7589 -0.0777 0.7249 0.071 Uiso 1 1 calc R . .
C3 C 0.6903(2) -0.06024(14) 0.80030(10) 0.0608(6) Uani 1 1 d . . .
H3 H 0.7476 -0.0899 0.8194 0.073 Uiso 1 1 calc R . .
C4 C 0.5992(2) -0.02468(14) 0.82950(9) 0.0600(6) Uani 1 1 d . . .
H4 H 0.5946 -0.0305 0.8680 0.072 Uiso 1 1 calc R . .
C5 C 0.51563(18) 0.01935(13) 0.80096(8) 0.0506(5) Uani 1 1 d . . .
H5 H 0.4537 0.0428 0.8205 0.061 Uiso 1 1 calc R . .
C6 C 0.52151(17) 0.02969(11) 0.74314(8) 0.0439(4) Uani 1 1 d . . .
C7 C 0.43439(16) 0.08001(12) 0.71492(8) 0.0448(4) Uani 1 1 d . . .
C8 C 0.28817(18) 0.16250(12) 0.70762(8) 0.0500(5) Uani 1 1 d . . .
C9 C 0.19300(18) 0.21313(13) 0.72679(9) 0.0549(4) Uani 1 1 d U . .
C10 C 0.1570(3) 0.22786(16) 0.77849(12) 0.0797(6) Uani 1 1 d U . .
H10 H 0.1876 0.2072 0.8117 0.096 Uiso 1 1 calc R . .
C11 C 0.0464(3) 0.2980(2) 0.7186(2) 0.1192(11) Uani 1 1 d U . .
H11 H -0.0103 0.3329 0.7032 0.143 Uiso 1 1 calc R . .
C12 C 0.0582(3) 0.2842(2) 0.7706(2) 0.1135(10) Uani 1 1 d U . .
H12 H 0.0116 0.3063 0.7988 0.136 Uiso 1 1 calc R . .
C13 C 0.4388(2) -0.10262(18) 0.54065(12) 0.0768(7) Uani 1 1 d . . .
H13 H 0.4850 -0.1273 0.5680 0.092 Uiso 1 1 calc R . .
C14 C 0.4493(2) -0.11214(16) 0.48641(12) 0.0739(7) Uani 1 1 d . . .
H14 H 0.5058 -0.1453 0.4693 0.089 Uiso 1 1 calc R . .
C15 C 0.3432(2) -0.04731(16) 0.54946(10) 0.0676(6) Uani 1 1 d . . .
H15 H 0.3147 -0.0283 0.5835 0.081 Uiso 1 1 calc R . .
C16 C 0.30245(18) -0.02818(13) 0.49870(8) 0.0506(5) Uani 1 1 d . . .
C17 C 0.21022(17) 0.02490(12) 0.47907(8) 0.0460(4) Uani 1 1 d . . .
C18 C 0.06227(16) 0.10596(11) 0.48617(8) 0.0436(4) Uani 1 1 d . . .
C19 C -0.02811(17) 0.15297(11) 0.51431(8) 0.0449(4) Uani 1 1 d . . .
C20 C -0.0336(2) 0.15232(14) 0.57234(8) 0.0561(5) Uani 1 1 d . . .
H20 H 0.0212 0.1216 0.5924 0.067 Uiso 1 1 calc R . .
C21 C -0.1188(2) 0.19629(16) 0.60067(10) 0.0681(6) Uani 1 1 d . . .
H21 H -0.1218 0.1951 0.6394 0.082 Uiso 1 1 calc R . .
C22 C -0.1992(2) 0.24200(16) 0.57048(10) 0.0694(7) Uani 1 1 d . . .
H22 H -0.2573 0.2715 0.5891 0.083 Uiso 1 1 calc R . .
C23 C -0.1948(2) 0.24447(14) 0.51373(10) 0.0627(6) Uani 1 1 d . . .
H23 H -0.2498 0.2762 0.4945 0.075 Uiso 1 1 calc R . .
C24 C -0.10964(17) 0.20061(12) 0.48344(9) 0.0497(5) Uani 1 1 d . . .
H24 H -0.151(3) 0.240(2) 0.4068(12) 0.101(10) Uiso 1 1 d . . .
H25 H -0.048(3) 0.1794(18) 0.4054(11) 0.088(9) Uiso 1 1 d . . .
H26 H 0.571(3) 0.038(2) 0.6382(13) 0.114(11) Uiso 1 1 d . . .
H27 H 0.687(3) -0.0175(18) 0.6396(11) 0.090(9) Uiso 1 1 d . . .
N1 N 0.42113(16) 0.09603(12) 0.66217(7) 0.0590(5) Uani 1 1 d . . .
N2 N 0.32480(17) 0.15051(12) 0.65742(7) 0.0614(5) Uani 1 1 d . . .
N3 N 0.18374(15) 0.04706(11) 0.42889(7) 0.0539(4) Uani 1 1 d . . .
N4 N 0.08649(15) 0.09995(11) 0.43376(7) 0.0520(4) Uani 1 1 d . . .
N5 N -0.1068(2) 0.20444(14) 0.42681(8) 0.0663(5) Uani 1 1 d . . .
N6 N 0.6220(2) -0.00150(19) 0.65716(9) 0.0861(8) Uani 1 1 d . . .
O1 O 0.35251(11) 0.12057(8) 0.74637(5) 0.0464(3) Uani 1 1 d . . .
O2 O 0.12790(17) 0.25512(12) 0.68818(9) 0.0917(6) Uani 1 1 d U . .
O3 O 0.13806(11) 0.05917(8) 0.51797(5) 0.0470(3) Uani 1 1 d . . .
O4 O 0.36709(14) -0.06722(10) 0.45855(7) 0.0647(4) Uani 1 1 d . . .


_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 N6 1.355(3) . ?
C1 C2 1.402(3) . ?
C1 C6 1.407(3) . ?
C2 C3 1.363(3) . ?
C3 C4 1.381(3) . ?
C4 C5 1.371(3) . ?
C5 C6 1.397(3) . ?
C6 C7 1.447(3) . ?
C7 N1 1.298(2) . ?
C7 O1 1.367(2) . ?
C8 N2 1.290(3) . ?
C8 O1 1.360(2) . ?
C8 C9 1.432(3) . ?
C9 C10 1.328(3) . ?
C9 O2 1.363(3) . ?
C10 C12 1.457(5) . ?
C11 C12 1.273(5) . ?
C11 O2 1.368(4) . ?
C13 C14 1.315(4) . ?
C13 C15 1.420(4) . ?
C14 O4 1.358(3) . ?
C15 C16 1.339(3) . ?
C16 O4 1.364(2) . ?
C16 C17 1.432(3) . ?
C17 N3 1.289(2) . ?
C17 O3 1.361(2) . ?
C18 N4 1.291(2) . ?
C18 O3 1.374(2) . ?
C18 C19 1.445(3) . ?
C19 C20 1.393(3) . ?
C19 C24 1.412(3) . ?
C20 C21 1.380(3) . ?
C21 C22 1.379(3) . ?
C22 C23 1.362(3) . ?
C23 C24 1.403(3) . ?
C24 N5 1.360(3) . ?
N1 N2 1.408(3) . ?
N3 N4 1.402(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
N6 C1 C2 120.2(2) . . ?
N6 C1 C6 122.0(2) . . ?
C2 C1 C6 117.81(19) . . ?
C3 C2 C1 121.4(2) . . ?
C2 C3 C4 120.8(2) . . ?
C5 C4 C3 119.1(2) . . ?
C4 C5 C6 121.34(19) . . ?
C5 C6 C1 119.44(18) . . ?
C5 C6 C7 119.59(17) . . ?
C1 C6 C7 120.95(17) . . ?
N1 C7 O1 111.42(17) . . ?
N1 C7 C6 130.04(17) . . ?
O1 C7 C6 118.51(15) . . ?
N2 C8 O1 112.81(18) . . ?
N2 C8 C9 129.21(19) . . ?
O1 C8 C9 117.98(18) . . ?
C10 C9 O2 112.2(2) . . ?
C10 C9 C8 129.5(2) . . ?
O2 C9 C8 118.3(2) . . ?
C9 C10 C12 103.3(3) . . ?
C12 C11 O2 111.4(3) . . ?
C11 C12 C10 108.3(3) . . ?
C14 C13 C15 106.8(2) . . ?
C13 C14 O4 111.3(2) . . ?
C16 C15 C13 106.0(2) . . ?
C15 C16 O4 110.37(19) . . ?
C15 C16 C17 133.7(2) . . ?
O4 C16 C17 115.92(18) . . ?
N3 C17 O3 112.78(17) . . ?
N3 C17 C16 129.82(18) . . ?
O3 C17 C16 117.39(17) . . ?
N4 C18 O3 111.29(16) . . ?
N4 C18 C19 130.39(18) . . ?
O3 C18 C19 118.32(16) . . ?
C20 C19 C24 119.79(18) . . ?
C20 C19 C18 119.69(18) . . ?
C24 C19 C18 120.51(17) . . ?
C21 C20 C19 121.4(2) . . ?
C20 C21 C22 118.8(2) . . ?
C23 C22 C21 120.9(2) . . ?
C22 C23 C24 122.0(2) . . ?
N5 C24 C23 120.8(2) . . ?
N5 C24 C19 122.1(2) . . ?
C23 C24 C19 117.15(19) . . ?
C7 N1 N2 106.86(16) . . ?
C8 N2 N1 105.80(16) . . ?
C17 N3 N4 105.81(15) . . ?
C18 N4 N3 107.33(16) . . ?
C8 O1 C7 103.12(15) . . ?
C9 O2 C11 104.8(3) . . ?
C17 O3 C18 102.78(14) . . ?
C14 O4 C16 105.62(18) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.21
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.046
