# 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_C15H14N4O2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 N4 O2'
_chemical_formula_weight         282.30

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

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

_cell_length_a                   8.2193(12)
_cell_length_b                   8.2471(12)
_cell_length_c                   11.2596(16)
_cell_angle_alpha                103.760(3)
_cell_angle_beta                 91.764(3)
_cell_angle_gamma                110.780(3)
_cell_volume                     687.51(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1330
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      23.17

_exptl_crystal_description       prismatic
_exptl_crystal_colour            amber
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.094
_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      296(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            5308
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2354
_reflns_number_gt                1415
_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)+(0.0330P)²+0.0000P] 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         2354
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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 0.2271(2) 0.9896(2) 0.56184(17) 0.0477(5) Uani 1 1 d . . .
C2 C 0.1748(2) 0.9739(2) 0.67775(16) 0.0456(5) Uani 1 1 d . . .
C3 C -0.0656(2) 0.7194(2) 0.58445(17) 0.0489(5) Uani 1 1 d . . .
C4 C -0.0088(2) 0.7336(3) 0.47247(18) 0.0570(5) Uani 1 1 d . . .
H4 H -0.0731 0.6453 0.4020 0.068 Uiso 1 1 calc R . .
C5 C 0.3858(2) 1.1424(2) 0.54905(18) 0.0650(6) Uani 1 1 d . . .
H5A H 0.3937 1.1360 0.4633 0.098 Uiso 1 1 calc R . .
H5B H 0.4890 1.1348 0.5857 0.098 Uiso 1 1 calc R . .
H5C H 0.3766 1.2544 0.5900 0.098 Uiso 1 1 calc R . .
C6 C -0.2293(2) 0.5709(2) 0.59726(18) 0.0662(6) Uani 1 1 d . . .
H6A H -0.1996 0.5029 0.6467 0.099 Uiso 1 1 calc R . .
H6B H -0.2838 0.4932 0.5171 0.099 Uiso 1 1 calc R . .
H6C H -0.3090 0.6216 0.6361 0.099 Uiso 1 1 calc R . .
C7 C 0.2855(2) 1.1091(2) 0.79301(17) 0.0582(6) Uani 1 1 d . . .
H7A H 0.4078 1.1326 0.7827 0.070 Uiso 1 1 calc R . .
H7B H 0.2674 1.2208 0.8001 0.070 Uiso 1 1 calc R . .
C8 C 0.2536(2) 1.0590(2) 0.91165(16) 0.0496(5) Uani 1 1 d . . .
C9 C 0.2020(2) 1.1596(3) 1.00660(18) 0.0582(5) Uani 1 1 d . . .
H9 H 0.1832 1.2635 1.0041 0.070 Uiso 1 1 calc R . .
C10 C 0.2149(2) 0.9344(3) 1.07548(17) 0.0530(5) Uani 1 1 d . . .
C11 C 0.2024(3) 0.8155(3) 1.14598(19) 0.0683(6) Uani 1 1 d . . .
H11 H 0.1695 0.8361 1.2248 0.082 Uiso 1 1 calc R . .
C12 C 0.2400(3) 0.6664(3) 1.0965(2) 0.0824(7) Uani 1 1 d . . .
H12 H 0.2300 0.5832 1.1416 0.099 Uiso 1 1 calc R . .
C13 C 0.2928(3) 0.6376(3) 0.9799(2) 0.0724(6) Uani 1 1 d . . .
H13 H 0.3201 0.5368 0.9483 0.087 Uiso 1 1 calc R . .
C14 C 0.3049(2) 0.7575(3) 0.91099(17) 0.0530(5) Uani 1 1 d . . .
C15 C 0.2653(2) 0.9120(2) 0.95395(16) 0.0461(5) Uani 1 1 d . . .
N1 N 0.1344(2) 0.8679(2) 0.45931(14) 0.0575(5) Uani 1 1 d . . .
N2 N 0.02846(18) 0.84234(19) 0.68820(13) 0.0479(4) Uani 1 1 d . . .
N3 N 0.18135(19) 1.0889(2) 1.10550(14) 0.0594(5) Uani 1 1 d . . .
H3 H 0.1219 1.1341 1.1791 0.071 Uiso 1 1 d R . .
N4 N 0.3679(2) 0.7174(3) 0.79135(15) 0.0625(5) Uani 1 1 d . . .
O1 O 0.42380(18) 0.8372(2) 0.74058(13) 0.0762(5) Uani 1 1 d . . .
O2 O 0.3665(2) 0.5657(2) 0.74733(15) 0.1036(6) 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 N1 1.332(2) . ?
C1 C2 1.407(2) . ?
C1 C5 1.497(2) . ?
C2 N2 1.335(2) . ?
C2 C7 1.508(2) . ?
C3 N2 1.347(2) . ?
C3 C4 1.375(2) . ?
C3 C6 1.503(2) . ?
C4 N1 1.340(2) . ?
C4 H4 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.494(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.366(2) . ?
C8 C15 1.436(2) . ?
C9 N3 1.364(2) . ?
C9 H9 0.9300 . ?
C10 N3 1.365(2) . ?
C10 C11 1.381(2) . ?
C10 C15 1.431(2) . ?
C11 C12 1.368(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.405(2) . ?
C14 N4 1.465(2) . ?
N3 H3 1.0354 . ?
N4 O1 1.2152(18) . ?
N4 O2 1.2271(19) . ?

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
N1 C1 C2 120.32(16) . . ?
N1 C1 C5 117.90(16) . . ?
C2 C1 C5 121.78(18) . . ?
N2 C2 C1 121.48(17) . . ?
N2 C2 C7 119.04(15) . . ?
C1 C2 C7 119.47(16) . . ?
N2 C3 C4 119.36(17) . . ?
N2 C3 C6 117.77(16) . . ?
C4 C3 C6 122.87(17) . . ?
N1 C4 C3 123.54(18) . . ?
N1 C4 H4 118.2 . . ?
C3 C4 H4 118.2 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C2 116.84(14) . . ?
C8 C7 H7A 108.1 . . ?
C2 C7 H7A 108.1 . . ?
C8 C7 H7B 108.1 . . ?
C2 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
C9 C8 C15 105.70(16) . . ?
C9 C8 C7 121.94(19) . . ?
C15 C8 C7 132.36(16) . . ?
N3 C9 C8 111.72(18) . . ?
N3 C9 H9 124.1 . . ?
C8 C9 H9 124.1 . . ?
N3 C10 C11 127.84(19) . . ?
N3 C10 C15 108.00(17) . . ?
C11 C10 C15 124.2(2) . . ?
C10 C11 C12 118.0(2) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C11 C12 C13 121.0(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 122.36(18) . . ?
C13 C14 N4 115.69(19) . . ?
C15 C14 N4 121.92(18) . . ?
C14 C15 C10 114.22(18) . . ?
C14 C15 C8 139.37(17) . . ?
C10 C15 C8 106.38(17) . . ?
C1 N1 C4 117.05(15) . . ?
C2 N2 C3 118.17(15) . . ?
C10 N3 C9 108.15(16) . . ?
C10 N3 H3 128.4 . . ?
C9 N3 H3 121.9 . . ?
O1 N4 O2 122.32(18) . . ?
O1 N4 C14 118.68(17) . . ?
O2 N4 C14 118.98(18) . . ?

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
N1 C1 C2 N2 -2.8(3) . . . . ?
C5 C1 C2 N2 176.69(16) . . . . ?
N1 C1 C2 C7 177.57(16) . . . . ?
C5 C1 C2 C7 -2.9(2) . . . . ?
N2 C3 C4 N1 -2.2(3) . . . . ?
C6 C3 C4 N1 178.22(17) . . . . ?
N2 C2 C7 C8 16.9(2) . . . . ?
C1 C2 C7 C8 -163.49(16) . . . . ?
C2 C7 C8 C9 -120.05(19) . . . . ?
C2 C7 C8 C15 59.7(3) . . . . ?
C15 C8 C9 N3 0.4(2) . . . . ?
C7 C8 C9 N3 -179.79(15) . . . . ?
N3 C10 C11 C12 178.99(19) . . . . ?
C15 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 C13 1.4(3) . . . . ?
C11 C12 C13 C14 -1.3(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C12 C13 C14 N4 177.86(19) . . . . ?
C13 C14 C15 C10 1.1(3) . . . . ?
N4 C14 C15 C10 -176.69(15) . . . . ?
C13 C14 C15 C8 -176.4(2) . . . . ?
N4 C14 C15 C8 5.9(3) . . . . ?
N3 C10 C15 C14 179.69(14) . . . . ?
C11 C10 C15 C14 -1.0(3) . . . . ?
N3 C10 C15 C8 -2.05(19) . . . . ?
C11 C10 C15 C8 177.32(17) . . . . ?
C9 C8 C15 C14 178.6(2) . . . . ?
C7 C8 C15 C14 -1.2(3) . . . . ?
C9 C8 C15 C10 1.00(19) . . . . ?
C7 C8 C15 C10 -178.77(18) . . . . ?
C2 C1 N1 C4 0.5(2) . . . . ?
C5 C1 N1 C4 -179.01(16) . . . . ?
C3 C4 N1 C1 1.9(3) . . . . ?
C1 C2 N2 C3 2.6(2) . . . . ?
C7 C2 N2 C3 -177.83(15) . . . . ?
C4 C3 N2 C2 -0.2(2) . . . . ?
C6 C3 N2 C2 179.46(15) . . . . ?
C11 C10 N3 C9 -177.02(18) . . . . ?
C15 C10 N3 C9 2.31(19) . . . . ?
C8 C9 N3 C10 -1.7(2) . . . . ?
C13 C14 N4 O1 -161.47(18) . . . . ?
C15 C14 N4 O1 16.4(3) . . . . ?
C13 C14 N4 O2 16.8(3) . . . . ?
C15 C14 N4 O2 -165.32(18) . . . . ?

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
N3 H3 N2 1.04 1.99 3.001(2) 166.0 2_577

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.030

#=========================================================================END   

_database_code_depnum_ccdc_archive 'CCDC 953438'
