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

 
data_shelx
 
_audit_creation_method            SHELXL-2014
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H11 N O3' 
_chemical_formula_weight          241.24

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'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    6.9160(7)
_cell_length_b                    8.3188(8)
_cell_length_c                    10.4144(9)
_cell_angle_alpha                 76.992(3)
_cell_angle_beta                  76.986(3)
_cell_angle_gamma                 86.369(4)
_cell_volume                      568.75(9)
_cell_formula_units_Z             2
_cell_measurement_temperature     218(2)
_cell_measurement_reflns_used     2002 
_cell_measurement_theta_min       2.882 
_cell_measurement_theta_max       24.987 
 
_exptl_crystal_description        Needle 
_exptl_crystal_colour             Yellow 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.409          
_exptl_crystal_F_000              252
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.250
_exptl_crystal_size_mid           0.120
_exptl_crystal_size_min           0.090
_exptl_absorpt_coefficient_mu     0.100
_shelx_estimated_absorpt_T_min    0.975
_shelx_estimated_absorpt_T_max    0.991
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.963 
_exptl_absorpt_correction_T_max   0.985 
_exptl_absorpt_process_details    'SADABS' 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       218(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'sealed tube'                       
_diffrn_measurement_device_type   'Bruker P4' 
_diffrn_measurement_method        'ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             ?
_diffrn_reflns_av_unetI/netI      0.0184
_diffrn_reflns_av_R_equivalents   ?
_diffrn_reflns_limit_h_min        ?
_diffrn_reflns_limit_h_max        ?
_diffrn_reflns_limit_k_min        ?
_diffrn_reflns_limit_k_max        ?
_diffrn_reflns_limit_l_min        ?
_diffrn_reflns_limit_l_max        ?
_diffrn_reflns_theta_min          2.882
_diffrn_reflns_theta_max          24.987
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.973
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.973
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.973
_reflns_number_total              2002
_reflns_number_gt                 1582
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker XSCANS'
_computing_cell_refinement        'Bruker XSCANS'
_computing_data_reduction         'Bruker SHELXTL'
_computing_structure_solution     'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_refine_special_details
;
 ?
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0576P)²+0.1522P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2002
_refine_ls_number_parameters      163
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0516
_refine_ls_R_factor_gt            0.0398
_refine_ls_wR_factor_ref          0.1182
_refine_ls_wR_factor_gt           0.1103
_refine_ls_goodness_of_fit_ref    1.077
_refine_ls_restrained_S_all       1.077
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.1781(3) 0.3761(2) 0.94082(17) 0.0437(4) Uani 1 1 d . . . . .
C2 C -0.0053(2) 0.3827(2) 0.78144(17) 0.0424(4) Uani 1 1 d . . . . .
C3 C 0.1649(2) 0.49176(19) 0.71866(16) 0.0373(4) Uani 1 1 d . . . . .
C4 C 0.2784(2) 0.48521(19) 0.81636(16) 0.0389(4) Uani 1 1 d . . . . .
C5 C 0.4516(2) 0.5693(2) 0.78676(16) 0.0413(4) Uani 1 1 d . . . . .
H5 H 0.5259 0.5634 0.8518 0.050 Uiso 1 1 calc R U . . .
C6 C 0.5151(2) 0.66477(19) 0.65569(16) 0.0383(4) Uani 1 1 d . . . . .
C7 C 0.3989(2) 0.67477(18) 0.55585(16) 0.0360(4) Uani 1 1 d . . . . .
C8 C 0.2195(2) 0.58361(19) 0.59098(16) 0.0381(4) Uani 1 1 d . . . . .
H8 H 0.1419 0.5870 0.5281 0.046 Uiso 1 1 calc R U . . .
C9 C 0.4640(2) 0.7709(2) 0.42558(17) 0.0404(4) Uani 1 1 d . . . . .
H9 H 0.3861 0.7783 0.3624 0.049 Uiso 1 1 calc R U . . .
C10 C 0.6420(3) 0.8553(2) 0.38848(17) 0.0422(4) Uani 1 1 d . . . . .
C11 C 0.7564(3) 0.8426(2) 0.48866(18) 0.0477(4) Uani 1 1 d . . . . .
H11 H 0.8761 0.8979 0.4662 0.057 Uiso 1 1 calc R U . . .
C12 C 0.6951(2) 0.7523(2) 0.61521(18) 0.0451(4) Uani 1 1 d . . . . .
H12 H 0.7738 0.7475 0.6776 0.054 Uiso 1 1 calc R U . . .
C13 C 0.8881(3) 1.0423(3) 0.2240(2) 0.0665(6) Uani 1 1 d . . . . .
H13A H 0.9113 1.0953 0.1300 0.100 Uiso 1 1 calc R U . . .
H13B H 0.8715 1.1246 0.2773 0.100 Uiso 1 1 calc R U . . .
H13C H 0.9992 0.9720 0.2408 0.100 Uiso 1 1 calc R U . . .
C14 C 0.5847(4) 0.9726(3) 0.1623(2) 0.0675(6) Uani 1 1 d . . . . .
H14A H 0.6552 1.0367 0.0780 0.101 Uiso 1 1 calc R U . . .
H14B H 0.5496 0.8686 0.1491 0.101 Uiso 1 1 calc R U . . .
H14C H 0.4665 1.0312 0.1951 0.101 Uiso 1 1 calc R U . . .
N1 N 0.7100(2) 0.9444(2) 0.25990(15) 0.0576(4) Uani 1 1 d . . . . .
O1 O 0.00800(18) 0.31712(14) 0.91532(11) 0.0488(3) Uani 1 1 d . . . . .
O2 O 0.2147(2) 0.33406(17) 1.05039(13) 0.0620(4) Uani 1 1 d . . . . .
O3 O -0.13763(19) 0.34488(17) 0.73870(14) 0.0597(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 O2 1.195(2) . ?
C1 O1 1.403(2) . ?
C1 C4 1.460(2) . ?
C2 O3 1.191(2) . ?
C2 O1 1.400(2) . ?
C2 C3 1.468(2) . ?
C3 C8 1.359(2) . ?
C3 C4 1.408(2) . ?
C4 C5 1.365(2) . ?
C5 C6 1.405(2) . ?
C5 H5 0.9300 . ?
C6 C12 1.414(2) . ?
C6 C7 1.436(2) . ?
C7 C9 1.402(2) . ?
C7 C8 1.428(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.390(2) . ?
C9 H9 0.9300 . ?
C10 N1 1.370(2) . ?
C10 C11 1.427(3) . ?
C11 C12 1.351(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 N1 1.450(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N1 1.450(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
O2 C1 O1 119.84(15) . . ?
O2 C1 C4 132.66(17) . . ?
O1 C1 C4 107.49(14) . . ?
O3 C2 O1 120.40(15) . . ?
O3 C2 C3 132.24(16) . . ?
O1 C2 C3 107.36(14) . . ?
C8 C3 C4 122.15(15) . . ?
C8 C3 C2 130.39(15) . . ?
C4 C3 C2 107.44(14) . . ?
C5 C4 C3 121.47(15) . . ?
C5 C4 C1 130.74(15) . . ?
C3 C4 C1 107.78(14) . . ?
C4 C5 C6 118.45(15) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C12 122.26(15) . . ?
C5 C6 C7 120.61(15) . . ?
C12 C6 C7 117.12(15) . . ?
C9 C7 C8 121.05(15) . . ?
C9 C7 C6 119.94(15) . . ?
C8 C7 C6 119.01(15) . . ?
C3 C8 C7 118.30(15) . . ?
C3 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C10 C9 C7 121.69(16) . . ?
C10 C9 H9 119.2 . . ?
C7 C9 H9 119.2 . . ?
N1 C10 C9 121.95(17) . . ?
N1 C10 C11 120.46(16) . . ?
C9 C10 C11 117.57(16) . . ?
C12 C11 C10 121.67(16) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C6 122.01(16) . . ?
C11 C12 H12 119.0 . . ?
C6 C12 H12 119.0 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 N1 C13 121.82(17) . . ?
C10 N1 C14 120.45(16) . . ?
C13 N1 C14 116.45(16) . . ?
C2 O1 C1 109.92(13) . . ?
 
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
O3 C2 C3 C8 0.7(3) . . . . ?
O1 C2 C3 C8 179.79(16) . . . . ?
O3 C2 C3 C4 -177.74(19) . . . . ?
O1 C2 C3 C4 1.38(17) . . . . ?
C8 C3 C4 C5 -1.1(2) . . . . ?
C2 C3 C4 C5 177.49(15) . . . . ?
C8 C3 C4 C1 -179.91(15) . . . . ?
C2 C3 C4 C1 -1.34(17) . . . . ?
O2 C1 C4 C5 2.5(3) . . . . ?
O1 C1 C4 C5 -177.85(16) . . . . ?
O2 C1 C4 C3 -178.78(19) . . . . ?
O1 C1 C4 C3 0.83(17) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C1 C4 C5 C6 179.01(16) . . . . ?
C4 C5 C6 C12 -178.30(15) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C5 C6 C7 C9 179.86(14) . . . . ?
C12 C6 C7 C9 -1.2(2) . . . . ?
C5 C6 C7 C8 -1.2(2) . . . . ?
C12 C6 C7 C8 177.81(14) . . . . ?
C4 C3 C8 C7 0.5(2) . . . . ?
C2 C3 C8 C7 -177.71(15) . . . . ?
C9 C7 C8 C3 179.54(14) . . . . ?
C6 C7 C8 C3 0.6(2) . . . . ?
C8 C7 C9 C10 -177.56(15) . . . . ?
C6 C7 C9 C10 1.4(2) . . . . ?
C7 C9 C10 N1 177.49(15) . . . . ?
C7 C9 C10 C11 -0.7(2) . . . . ?
N1 C10 C11 C12 -178.34(17) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C6 0.3(3) . . . . ?
C5 C6 C12 C11 179.32(16) . . . . ?
C7 C6 C12 C11 0.4(2) . . . . ?
C9 C10 N1 C13 175.31(17) . . . . ?
C11 C10 N1 C13 -6.5(3) . . . . ?
C9 C10 N1 C14 8.7(3) . . . . ?
C11 C10 N1 C14 -173.17(17) . . . . ?
O3 C2 O1 C1 178.38(16) . . . . ?
C3 C2 O1 C1 -0.87(17) . . . . ?
O2 C1 O1 C2 179.72(16) . . . . ?
C4 C1 O1 C2 0.05(17) . . . . ?
 
_refine_diff_density_max    0.170
_refine_diff_density_min   -0.159
_refine_diff_density_rms    0.039

_shelxl_version_number 2014-3



