# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1051403'
_audit_update_record             
;
2015-02-26 deposited with the CCDC.
2015-03-31 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 N O3'
_chemical_formula_weight         215.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   4.9159(5)
_cell_length_b                   9.8984(11)
_cell_length_c                   11.3114(13)
_cell_angle_alpha                88.785(9)
_cell_angle_beta                 78.349(9)
_cell_angle_gamma                82.913(9)
_cell_volume                     534.95(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             224
_exptl_absorpt_coefficient_mu    0.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88796
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3979
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.99
_diffrn_reflns_theta_max         67.04
_reflns_number_total             1886
_reflns_number_gt                1139
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_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)+(0.1328P)²+0.0803P] 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         1886
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.2766
_refine_ls_wR_factor_gt          0.2119
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_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
O1 O 0.6351(8) 0.5384(3) 0.8468(3) 0.0975(11) Uani 1 1 d . . .
O2 O -0.0772(7) 0.3273(3) -0.0147(3) 0.1006(11) Uani 1 1 d . . .
O3 O -0.3792(7) 0.1973(3) -0.0391(3) 0.0987(10) Uani 1 1 d . . .
N1 N -0.2072(7) 0.2296(3) 0.0150(3) 0.0771(9) Uani 1 1 d . . .
C1 C 0.5081(10) 0.4715(5) 0.7664(4) 0.0844(12) Uani 1 1 d . . .
H1A H 0.3858 0.5379 0.7311 0.101 Uiso 1 1 calc R . .
H1B H 0.3947 0.4064 0.8110 0.101 Uiso 1 1 calc R . .
C2 C 0.7231(9) 0.3988(5) 0.6677(4) 0.0884(13) Uani 1 1 d . . .
H2A H 0.8403 0.4635 0.6249 0.106 Uiso 1 1 calc R . .
H2B H 0.8417 0.3306 0.7030 0.106 Uiso 1 1 calc R . .
C3 C 0.5930(8) 0.3328(4) 0.5818(3) 0.0800(11) Uani 1 1 d . . .
C4 C 0.4756(8) 0.2826(4) 0.5153(3) 0.0761(11) Uani 1 1 d . . .
C5 C 0.3360(8) 0.2262(4) 0.4383(3) 0.0742(10) Uani 1 1 d . . .
C6 C 0.2139(8) 0.1790(4) 0.3717(3) 0.0754(10) Uani 1 1 d . . .
C7 C 0.0591(7) 0.1258(4) 0.2921(3) 0.0676(9) Uani 1 1 d . . .
C8 C 0.0084(7) 0.2013(4) 0.1916(3) 0.0687(10) Uani 1 1 d . . .
H8 H 0.0804 0.2836 0.1736 0.082 Uiso 1 1 calc R . .
C9 C -0.1516(7) 0.1506(4) 0.1199(3) 0.0663(9) Uani 1 1 d . . .
C10 C -0.2568(8) 0.0280(4) 0.1415(3) 0.0744(10) Uani 1 1 d . . .
H10 H -0.3635 -0.0036 0.0912 0.089 Uiso 1 1 calc R . .
C11 C -0.2003(9) -0.0465(4) 0.2393(4) 0.0807(11) Uani 1 1 d . . .
H11 H -0.2686 -0.1299 0.2554 0.097 Uiso 1 1 calc R . .
C12 C -0.0436(9) 0.0010(4) 0.3138(3) 0.0768(10) Uani 1 1 d . . .
H12 H -0.0061 -0.0510 0.3795 0.092 Uiso 1 1 calc R . .
H1 H 0.709(12) 0.455(6) 0.897(5) 0.14(2) 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
O1 0.135(3) 0.088(2) 0.0870(19) -0.0061(15) -0.0460(19) -0.0400(19)
O2 0.105(2) 0.110(2) 0.098(2) 0.0298(18) -0.0352(18) -0.0379(19)
O3 0.109(2) 0.116(2) 0.0885(19) -0.0021(16) -0.0512(18) -0.0296(18)
N1 0.080(2) 0.089(2) 0.0685(18) -0.0002(16) -0.0218(15) -0.0237(17)
C1 0.097(3) 0.088(3) 0.079(2) -0.006(2) -0.031(2) -0.028(2)
C2 0.083(3) 0.105(3) 0.088(3) -0.011(2) -0.034(2) -0.026(2)
C3 0.081(3) 0.094(3) 0.073(2) -0.005(2) -0.025(2) -0.025(2)
C4 0.080(2) 0.092(3) 0.064(2) -0.0025(19) -0.0225(18) -0.026(2)
C5 0.077(2) 0.088(3) 0.064(2) -0.0039(18) -0.0214(18) -0.0214(19)
C6 0.077(2) 0.091(3) 0.065(2) -0.0020(18) -0.0195(18) -0.0245(19)
C7 0.067(2) 0.077(2) 0.0627(19) -0.0079(16) -0.0158(16) -0.0176(16)
C8 0.070(2) 0.074(2) 0.068(2) -0.0029(16) -0.0167(16) -0.0272(17)
C9 0.066(2) 0.075(2) 0.0612(19) -0.0041(16) -0.0159(16) -0.0191(16)
C10 0.078(2) 0.081(2) 0.070(2) -0.0140(18) -0.0165(18) -0.0291(19)
C11 0.095(3) 0.071(2) 0.083(2) -0.0032(19) -0.018(2) -0.034(2)
C12 0.092(3) 0.071(2) 0.072(2) 0.0037(17) -0.022(2) -0.0191(19)

_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
O1 C1 1.418(4) . ?
O1 H1 1.06(6) . ?
O2 N1 1.227(4) . ?
O3 N1 1.215(3) . ?
N1 C9 1.461(5) . ?
C1 C2 1.501(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.470(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.187(4) . ?
C4 C5 1.377(4) . ?
C5 C6 1.188(4) . ?
C6 C7 1.437(4) . ?
C7 C12 1.390(5) . ?
C7 C8 1.395(5) . ?
C8 C9 1.379(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(5) . ?
C10 C11 1.372(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

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
C1 O1 H1 101(3) . . ?
O3 N1 O2 122.5(3) . . ?
O3 N1 C9 119.4(3) . . ?
O2 N1 C9 118.1(3) . . ?
O1 C1 C2 111.4(4) . . ?
O1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C3 C2 C1 111.8(3) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 176.8(5) . . ?
C3 C4 C5 179.0(5) . . ?
C6 C5 C4 179.2(4) . . ?
C5 C6 C7 178.1(4) . . ?
C12 C7 C8 119.3(3) . . ?
C12 C7 C6 121.3(3) . . ?
C8 C7 C6 119.4(3) . . ?
C9 C8 C7 118.1(3) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C10 C9 C8 123.0(3) . . ?
C10 C9 N1 118.6(3) . . ?
C8 C9 N1 118.4(3) . . ?
C11 C10 C9 118.2(3) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?

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 -178.2(4) . . . . ?
C1 C2 C3 C4 7(8) . . . . ?
C2 C3 C4 C5 29(30) . . . . ?
C3 C4 C5 C6 24(49) . . . . ?
C4 C5 C6 C7 -28(40) . . . . ?
C5 C6 C7 C12 -117(12) . . . . ?
C5 C6 C7 C8 63(12) . . . . ?
C12 C7 C8 C9 2.3(6) . . . . ?
C6 C7 C8 C9 -177.1(3) . . . . ?
C7 C8 C9 C10 -1.6(6) . . . . ?
C7 C8 C9 N1 179.6(3) . . . . ?
O3 N1 C9 C10 11.7(6) . . . . ?
O2 N1 C9 C10 -168.6(4) . . . . ?
O3 N1 C9 C8 -169.5(4) . . . . ?
O2 N1 C9 C8 10.3(6) . . . . ?
C8 C9 C10 C11 0.3(6) . . . . ?
N1 C9 C10 C11 179.1(4) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C10 C11 C12 C7 0.4(7) . . . . ?
C8 C7 C12 C11 -1.7(6) . . . . ?
C6 C7 C12 C11 177.6(4) . . . . ?

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
O1 H1 O2 1.06(6) 1.94(6) 2.975(4) 166(4) 1_656
O1 H1 N1 1.06(6) 2.61(6) 3.650(4) 168(4) 1_656

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        67.04
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.054
