# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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.
#
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#  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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_ax0508

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 N2 O2'
_chemical_formula_weight         238.24

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           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   12.9282(5)
_cell_length_b                   13.3172(6)
_cell_length_c                   6.6540(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.290(1)
_cell_angle_gamma                90.00
_cell_volume                     1119.35(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4277
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      28.57

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX II Duo'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15678
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         28.85
_reflns_number_total             2926
_reflns_number_gt                2185
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0544P)²+0.4257P] 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         2926
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.85857(10) 0.32184(10) 0.2509(2) 0.0238(3) Uani 1 1 d . . .
C2 C 0.96602(10) 0.36642(10) 0.2822(2) 0.0215(3) Uani 1 1 d . . .
C3 C 1.06412(11) 0.32212(11) 0.3476(2) 0.0247(3) Uani 1 1 d . . .
H3 H 1.0703 0.2523 0.3772 0.030 Uiso 1 1 calc R . .
C4 C 1.15407(10) 0.38310(11) 0.3691(2) 0.0246(3) Uani 1 1 d . . .
C5 C 1.14235(11) 0.48571(11) 0.3246(2) 0.0256(3) Uani 1 1 d . . .
H5 H 1.2038 0.5264 0.3395 0.031 Uiso 1 1 calc R . .
C6 C 1.04336(11) 0.52984(11) 0.2593(2) 0.0239(3) Uani 1 1 d . . .
H6 H 1.0362 0.5996 0.2297 0.029 Uiso 1 1 calc R . .
C7 C 0.95581(10) 0.46818(10) 0.2393(2) 0.0214(3) Uani 1 1 d . . .
C8 C 0.84158(11) 0.49290(10) 0.1766(2) 0.0225(3) Uani 1 1 d . . .
C9 C 1.26245(11) 0.33920(12) 0.4413(3) 0.0338(4) Uani 1 1 d . . .
H9A H 1.3001 0.3398 0.3280 0.051 Uiso 1 1 calc R . .
H9B H 1.2562 0.2699 0.4870 0.051 Uiso 1 1 calc R . .
H9C H 1.3019 0.3792 0.5559 0.051 Uiso 1 1 calc R . .
C10 C 0.67539(10) 0.39133(10) 0.1434(2) 0.0255(3) Uani 1 1 d . . .
C11 C 0.62594(12) 0.34693(12) -0.0383(3) 0.0365(4) Uani 1 1 d . . .
H11 H 0.6652 0.3218 -0.1331 0.044 Uiso 1 1 calc R . .
C12 C 0.51616(12) 0.34029(13) -0.0776(3) 0.0412(4) Uani 1 1 d . . .
H12 H 0.4784 0.3102 -0.2010 0.049 Uiso 1 1 calc R . .
C13 C 0.46304(12) 0.37771(11) 0.0641(3) 0.0356(4) Uani 1 1 d . . .
H13 H 0.3880 0.3748 0.0401 0.043 Uiso 1 1 calc R . .
C14 C 0.52098(13) 0.41944(13) 0.2412(3) 0.0377(4) Uani 1 1 d . . .
H14 H 0.4837 0.4445 0.3392 0.045 Uiso 1 1 calc R . .
N1 N 0.78831(9) 0.40164(9) 0.18829(19) 0.0245(3) Uani 1 1 d . . .
N2 N 0.62703(10) 0.42713(10) 0.2847(2) 0.0326(3) Uani 1 1 d . . .
O1 O 0.83238(8) 0.23629(7) 0.27412(19) 0.0316(3) Uani 1 1 d . . .
O2 O 0.79899(8) 0.57216(7) 0.12404(16) 0.0284(3) 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
C1 0.0180(6) 0.0213(6) 0.0315(8) -0.0021(5) 0.0040(5) 0.0014(5)
C2 0.0185(6) 0.0218(6) 0.0240(7) -0.0024(5) 0.0038(5) -0.0009(5)
C3 0.0206(6) 0.0231(7) 0.0300(7) -0.0016(6) 0.0047(5) 0.0016(5)
C4 0.0185(6) 0.0302(7) 0.0249(7) -0.0039(6) 0.0043(5) 0.0006(5)
C5 0.0208(7) 0.0296(7) 0.0266(7) -0.0033(6) 0.0052(5) -0.0055(5)
C6 0.0247(7) 0.0234(7) 0.0230(7) -0.0004(5) 0.0035(5) -0.0033(5)
C7 0.0198(6) 0.0230(7) 0.0206(7) -0.0008(5) 0.0026(5) -0.0005(5)
C8 0.0203(6) 0.0221(6) 0.0241(7) -0.0019(5) 0.0026(5) -0.0007(5)
C9 0.0196(7) 0.0350(8) 0.0460(10) -0.0046(7) 0.0049(6) 0.0019(6)
C10 0.0167(6) 0.0192(6) 0.0388(8) 0.0000(6) 0.0019(6) 0.0001(5)
C11 0.0237(7) 0.0322(8) 0.0503(10) -0.0144(7) 0.0005(7) 0.0036(6)
C12 0.0250(8) 0.0324(8) 0.0588(11) -0.0119(8) -0.0076(7) -0.0011(6)
C13 0.0182(7) 0.0239(7) 0.0625(11) 0.0039(7) 0.0038(7) -0.0009(6)
C14 0.0243(8) 0.0382(9) 0.0529(11) 0.0013(8) 0.0136(7) 0.0003(6)
N1 0.0165(5) 0.0201(5) 0.0352(7) -0.0006(5) 0.0014(5) 0.0001(4)
N2 0.0222(6) 0.0357(7) 0.0403(8) -0.0022(6) 0.0078(5) -0.0020(5)
O1 0.0224(5) 0.0203(5) 0.0518(7) 0.0012(5) 0.0072(5) -0.0002(4)
O2 0.0261(5) 0.0219(5) 0.0354(6) 0.0023(4) 0.0023(4) 0.0028(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 O1 1.2078(17) . ?
C1 N1 1.4025(17) . ?
C1 C2 1.4840(18) . ?
C2 C3 1.3824(18) . ?
C2 C7 1.3855(19) . ?
C3 C4 1.4005(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(2) . ?
C4 C9 1.4998(19) . ?
C5 C6 1.3911(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.3817(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.4835(18) . ?
C8 O2 1.2075(16) . ?
C8 N1 1.4072(17) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N2 1.324(2) . ?
C10 C11 1.375(2) . ?
C10 N1 1.4330(17) . ?
C11 C12 1.390(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.373(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(2) . ?
C13 H13 0.9500 . ?
C14 N2 1.344(2) . ?
C14 H14 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
O1 C1 N1 124.84(12) . . ?
O1 C1 C2 129.71(13) . . ?
N1 C1 C2 105.44(11) . . ?
C3 C2 C7 121.54(12) . . ?
C3 C2 C1 129.95(13) . . ?
C7 C2 C1 108.49(11) . . ?
C2 C3 C4 118.09(13) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C5 C4 C3 119.63(12) . . ?
C5 C4 C9 120.00(13) . . ?
C3 C4 C9 120.36(13) . . ?
C6 C5 C4 121.98(13) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C7 C6 C5 117.34(13) . . ?
C7 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
C6 C7 C2 121.42(12) . . ?
C6 C7 C8 129.89(13) . . ?
C2 C7 C8 108.68(11) . . ?
O2 C8 N1 124.94(12) . . ?
O2 C8 C7 129.84(13) . . ?
N1 C8 C7 105.22(11) . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 125.31(14) . . ?
N2 C10 N1 115.57(13) . . ?
C11 C10 N1 119.13(14) . . ?
C10 C11 C12 117.24(16) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
C13 C12 C11 119.19(16) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 118.38(14) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
N2 C14 C13 124.16(16) . . ?
N2 C14 H14 117.9 . . ?
C13 C14 H14 117.9 . . ?
C1 N1 C8 112.16(11) . . ?
C1 N1 C10 123.78(11) . . ?
C8 N1 C10 124.06(11) . . ?
C10 N2 C14 115.72(14) . . ?

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
O1 C1 C2 C3 -0.6(3) . . . . ?
N1 C1 C2 C3 178.62(14) . . . . ?
O1 C1 C2 C7 -178.92(16) . . . . ?
N1 C1 C2 C7 0.32(16) . . . . ?
C7 C2 C3 C4 -0.2(2) . . . . ?
C1 C2 C3 C4 -178.35(14) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C2 C3 C4 C9 179.46(13) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C9 C4 C5 C6 -179.32(14) . . . . ?
C4 C5 C6 C7 -0.1(2) . . . . ?
C5 C6 C7 C2 -0.1(2) . . . . ?
C5 C6 C7 C8 179.07(14) . . . . ?
C3 C2 C7 C6 0.2(2) . . . . ?
C1 C2 C7 C6 178.71(13) . . . . ?
C3 C2 C7 C8 -179.08(13) . . . . ?
C1 C2 C7 C8 -0.60(15) . . . . ?
C6 C7 C8 O2 2.0(3) . . . . ?
C2 C7 C8 O2 -178.80(15) . . . . ?
C6 C7 C8 N1 -178.58(14) . . . . ?
C2 C7 C8 N1 0.65(15) . . . . ?
N2 C10 C11 C12 0.8(3) . . . . ?
N1 C10 C11 C12 -178.73(14) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 N2 0.7(3) . . . . ?
O1 C1 N1 C8 179.40(15) . . . . ?
C2 C1 N1 C8 0.11(16) . . . . ?
O1 C1 N1 C10 0.0(2) . . . . ?
C2 C1 N1 C10 -179.33(13) . . . . ?
O2 C8 N1 C1 179.02(14) . . . . ?
C7 C8 N1 C1 -0.46(16) . . . . ?
O2 C8 N1 C10 -1.5(2) . . . . ?
C7 C8 N1 C10 178.97(13) . . . . ?
N2 C10 N1 C1 105.13(16) . . . . ?
C11 C10 N1 C1 -75.3(2) . . . . ?
N2 C10 N1 C8 -74.24(18) . . . . ?
C11 C10 N1 C8 105.35(17) . . . . ?
C11 C10 N2 C14 -0.9(2) . . . . ?
N1 C10 N2 C14 178.69(13) . . . . ?
C13 C14 N2 C10 0.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.85
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 999881'
