# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_liuzhenxing
_audit_creation_date             2012-11-23
_audit_creation_method           
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H11 N3 O2'
_chemical_formula_sum            'C14 H11 N3 O2'
_chemical_formula_weight         253.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H11N3O2
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   12.2236(12)
_cell_length_b                   9.7043(5)
_cell_length_c                   19.5840(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2323.1(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2806
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.2919
_cell_measurement_theta_min      3.3864
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5437
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.39
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9868
_diffrn_measured_fraction_theta_max 0.8971
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -21.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7128   77.0000  -30.0000 109
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0575846000
_diffrn_orient_matrix_UB_12      0.0052336000
_diffrn_orient_matrix_UB_13      0.0042653000
_diffrn_orient_matrix_UB_21      0.0073004000
_diffrn_orient_matrix_UB_22      0.0089360000
_diffrn_orient_matrix_UB_23      0.0356029000
_diffrn_orient_matrix_UB_31      0.0033220000
_diffrn_orient_matrix_UB_32      0.0722993000
_diffrn_orient_matrix_UB_33      -0.0047777000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1987
_reflns_number_total             2267
_reflns_odcompleteness_completeness 98.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0519P)²+0.6734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0996
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.74663(10) 0.45800(13) 0.57639(6) 0.0152(3) Uani 1 1 d . . .
C2 C 0.68513(10) 0.36578(13) 0.53731(7) 0.0166(3) Uani 1 1 d . . .
H2 H 0.7170 0.3051 0.5064 0.020 Uiso 1 1 calc R . .
C3 C 0.57400(11) 0.37130(13) 0.54792(6) 0.0167(3) Uani 1 1 d . . .
C4 C 0.52243(11) 0.46172(14) 0.59318(7) 0.0187(3) Uani 1 1 d . . .
H4 H 0.4467 0.4610 0.5976 0.022 Uiso 1 1 calc R . .
C5 C 0.58439(10) 0.55135(14) 0.63091(7) 0.0175(3) Uani 1 1 d . . .
H5 H 0.5512 0.6116 0.6615 0.021 Uiso 1 1 calc R . .
C6 C 0.69937(10) 0.55133(13) 0.62293(7) 0.0146(3) Uani 1 1 d . . .
C7 C 0.79125(10) 0.61971(13) 0.65338(7) 0.0148(3) Uani 1 1 d . . .
C8 C 0.79472(10) 0.72509(13) 0.70703(7) 0.0149(3) Uani 1 1 d . . .
C9 C 0.70066(10) 0.79585(14) 0.72682(7) 0.0174(3) Uani 1 1 d . . .
H9 H 0.6345 0.7764 0.7054 0.021 Uiso 1 1 calc R . .
C10 C 0.70401(10) 0.89429(14) 0.77766(7) 0.0183(3) Uani 1 1 d . . .
H10 H 0.6400 0.9401 0.7897 0.022 Uiso 1 1 calc R . .
C11 C 0.80085(10) 0.92640(14) 0.81119(7) 0.0180(3) Uani 1 1 d . . .
C12 C 0.89527(11) 0.85641(15) 0.79075(7) 0.0219(3) Uani 1 1 d . . .
H12 H 0.9615 0.8768 0.8119 0.026 Uiso 1 1 calc R . .
C13 C 0.89275(11) 0.75784(14) 0.74007(7) 0.0200(3) Uani 1 1 d . . .
H13 H 0.9569 0.7127 0.7277 0.024 Uiso 1 1 calc R . .
C14 C 0.80432(12) 1.03192(15) 0.86721(8) 0.0243(3) Uani 1 1 d . . .
H14A H 0.7520 1.1033 0.8578 0.036 Uiso 1 1 calc R . .
H14B H 0.8763 1.0712 0.8697 0.036 Uiso 1 1 calc R . .
H14C H 0.7868 0.9888 0.9100 0.036 Uiso 1 1 calc R . .
N1 N 0.88455(9) 0.57198(11) 0.62712(6) 0.0171(3) Uani 1 1 d . . .
N2 N 0.85675(9) 0.47487(12) 0.58075(6) 0.0175(3) Uani 1 1 d . . .
N3 N 0.50497(9) 0.27297(12) 0.51130(6) 0.0198(3) Uani 1 1 d . . .
O1 O 0.54844(8) 0.19239(10) 0.47111(5) 0.0268(3) Uani 1 1 d . . .
O2 O 0.40597(8) 0.27382(11) 0.52221(5) 0.0274(3) Uani 1 1 d . . .
H2A H 0.9103(14) 0.4279(18) 0.5591(9) 0.027(4) 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
C1 0.0140(6) 0.0160(6) 0.0157(6) 0.0028(5) 0.0004(5) 0.0007(5)
C2 0.0185(7) 0.0163(6) 0.0151(6) 0.0003(5) -0.0003(5) 0.0011(5)
C3 0.0186(7) 0.0166(7) 0.0147(6) 0.0018(5) -0.0033(5) -0.0032(5)
C4 0.0134(6) 0.0232(7) 0.0194(7) 0.0015(6) 0.0001(5) -0.0013(5)
C5 0.0156(6) 0.0203(7) 0.0165(7) -0.0011(5) 0.0013(5) 0.0011(5)
C6 0.0166(7) 0.0137(6) 0.0136(6) 0.0017(5) -0.0010(5) 0.0009(5)
C7 0.0142(6) 0.0143(6) 0.0159(6) 0.0024(5) 0.0000(5) 0.0015(5)
C8 0.0169(7) 0.0134(6) 0.0144(6) 0.0024(5) 0.0003(5) -0.0009(5)
C9 0.0138(7) 0.0185(7) 0.0199(7) -0.0001(6) -0.0010(5) -0.0003(5)
C10 0.0165(7) 0.0174(7) 0.0210(7) -0.0010(6) 0.0025(5) 0.0021(5)
C11 0.0204(7) 0.0166(7) 0.0169(7) 0.0005(5) 0.0003(5) -0.0001(5)
C12 0.0168(7) 0.0242(7) 0.0249(7) -0.0054(6) -0.0056(5) 0.0013(6)
C13 0.0140(6) 0.0223(7) 0.0236(7) -0.0035(6) -0.0016(5) 0.0032(5)
C14 0.0250(8) 0.0247(8) 0.0232(7) -0.0073(6) -0.0018(6) 0.0019(6)
N1 0.0163(5) 0.0166(6) 0.0185(6) -0.0027(5) 0.0007(4) 0.0002(5)
N2 0.0149(6) 0.0177(6) 0.0199(6) -0.0052(5) 0.0010(5) 0.0006(5)
N3 0.0200(6) 0.0205(6) 0.0189(6) 0.0012(5) -0.0031(5) -0.0032(5)
O1 0.0272(6) 0.0249(6) 0.0282(6) -0.0105(5) -0.0040(4) -0.0002(4)
O2 0.0175(5) 0.0338(6) 0.0308(6) -0.0047(5) -0.0007(4) -0.0087(4)

_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 1.3970(19) . ?
C1 C6 1.4088(18) . ?
C1 N2 1.3587(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.3752(18) . ?
C3 C4 1.3976(19) . ?
C3 N3 1.4619(17) . ?
C4 H4 0.9300 . ?
C4 C5 1.3697(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.4142(17) . ?
C6 C7 1.4343(17) . ?
C7 C8 1.4669(19) . ?
C7 N1 1.3340(16) . ?
C8 C9 1.3942(18) . ?
C8 C13 1.3984(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.3891(18) . ?
C11 C12 1.3977(19) . ?
C11 C14 1.5013(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(2) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N1 N2 1.3522(16) . ?
N2 H2A 0.904(18) . ?
N3 O1 1.2301(15) . ?
N3 O2 1.2289(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
C2 C1 C6 123.07(12) . . ?
N2 C1 C2 130.14(12) . . ?
N2 C1 C6 106.75(11) . . ?
C1 C2 H2 122.5 . . ?
C3 C2 C1 115.07(12) . . ?
C3 C2 H2 122.5 . . ?
C2 C3 C4 124.46(12) . . ?
C2 C3 N3 118.07(12) . . ?
C4 C3 N3 117.43(12) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.43(12) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.33(12) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 118.63(12) . . ?
C1 C6 C7 104.20(11) . . ?
C5 C6 C7 137.07(12) . . ?
C6 C7 C8 130.02(11) . . ?
N1 C7 C6 110.40(11) . . ?
N1 C7 C8 119.57(11) . . ?
C9 C8 C7 121.23(11) . . ?
C9 C8 C13 117.79(12) . . ?
C13 C8 C7 120.98(11) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.12(12) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.43(12) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C12 117.34(13) . . ?
C10 C11 C14 121.50(12) . . ?
C12 C11 C14 121.16(12) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.66(13) . . ?
C13 C12 H12 119.2 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.65(12) . . ?
C12 C13 H13 119.7 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 N1 N2 106.62(10) . . ?
C1 N2 H2A 128.9(11) . . ?
N1 N2 C1 112.03(11) . . ?
N1 N2 H2A 119.0(11) . . ?
O1 N3 C3 118.66(11) . . ?
O2 N3 C3 118.60(11) . . ?
O2 N3 O1 122.74(11) . . ?

_database_code_depnum_ccdc_archive 'CCDC 985185'
