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

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#
#                 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
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data_sad
_audit_creation_date             2014-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.12 svn.r2899 for OlexSys, GUI svn.r4796)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H9 N O4'
_chemical_formula_sum            'C15 H9 N O4'
_chemical_formula_weight         267.23
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   11.595(4)
_cell_length_b                   3.8440(14)
_cell_length_c                   26.917(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1199.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    819
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.43
_cell_measurement_theta_min      3.51
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             552
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7992
_diffrn_reflns_point_group_measured_fraction_full 0.798
_diffrn_reflns_point_group_measured_fraction_max 0.763
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.121
_diffrn_reflns_theta_min         3.027
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.507
_reflns_Friedel_fraction_full    0.591
_reflns_Friedel_fraction_max     0.524
_reflns_number_gt                1438
_reflns_number_total             2716
_reflns_special_details          
;
 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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 420 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.848
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2716
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      0.848
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1623
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C3(H3), C12(H12), C9(H9), C2(H2), C15(H15), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
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
O3 O 0.4932(3) 0.7768(8) 0.23712(12) 0.0479(8) Uani 1 1 d . . . . .
C5 C 0.4780(4) 0.8796(11) 0.10269(18) 0.0414(10) Uani 1 1 d . . . . .
O2 O 0.4024(3) 0.7929(8) 0.06510(12) 0.0552(9) Uani 1 1 d . . . . .
C7 C 0.5177(4) 0.8768(10) 0.18846(16) 0.0401(10) Uani 1 1 d . . . . .
C6 C 0.4443(4) 0.7920(10) 0.15004(17) 0.0421(10) Uani 1 1 d . . . . .
H6 H 0.3746 0.6796 0.1559 0.050 Uiso 1 1 calc R . . . .
C4 C 0.5815(4) 1.0467(11) 0.09275(18) 0.0438(10) Uani 1 1 d . . . . .
C8 C 0.6208(4) 1.0464(11) 0.1806(2) 0.0473(11) Uani 1 1 d . . . . .
H8 H 0.6682 1.1045 0.2072 0.057 Uiso 1 1 calc R . . . .
N8 N 0.4591(3) 0.5930(11) 0.33148(14) 0.0498(10) Uani 1 1 d . . . . .
C3 C 0.6077(5) 1.1236(13) 0.0417(2) 0.0581(14) Uani 1 1 d . . . . .
H3 H 0.6769 1.2318 0.0337 0.070 Uiso 1 1 calc R . . . .
C12 C 0.2592(4) 0.7432(13) 0.32596(19) 0.0528(12) Uani 1 1 d . . . . .
H12 H 0.1990 0.8371 0.3075 0.063 Uiso 1 1 calc R . . . .
O4 O 0.3229(3) 1.0518(10) 0.23479(14) 0.0640(10) Uani 1 1 d . . . . .
C9 C 0.6525(4) 1.1282(11) 0.1330(2) 0.0527(13) Uani 1 1 d . . . . .
H9 H 0.7225 1.2397 0.1273 0.063 Uiso 1 1 calc R . . . .
C10 C 0.3895(4) 0.8721(12) 0.25648(17) 0.0442(10) Uani 1 1 d . . . . .
C11 C 0.3699(4) 0.7279(11) 0.30690(19) 0.0435(10) Uani 1 1 d . . . . .
C1 C 0.4259(5) 0.8653(15) 0.0158(2) 0.0612(14) Uani 1 1 d . . . . .
C2 C 0.5330(5) 1.0406(15) 0.0058(2) 0.0637(15) Uani 1 1 d . . . . .
H2 H 0.5510 1.0984 -0.0268 0.076 Uiso 1 1 calc R . . . .
C15 C 0.4380(5) 0.4729(14) 0.3771(2) 0.0568(13) Uani 1 1 d . . . . .
H15 H 0.4993 0.3814 0.3952 0.068 Uiso 1 1 calc R . . . .
O1 O 0.3551(5) 0.7718(15) -0.01412(17) 0.0909(15) Uani 1 1 d . . . . .
C13 C 0.2408(5) 0.6151(15) 0.3731(2) 0.0625(14) Uani 1 1 d . . . . .
H13 H 0.1675 0.6230 0.3871 0.075 Uiso 1 1 calc R . . . .
C14 C 0.3307(5) 0.4766(13) 0.3991(2) 0.0585(13) Uani 1 1 d . . . . .
H14 H 0.3198 0.3871 0.4309 0.070 Uiso 1 1 calc R . . . .

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
O3 0.0393(18) 0.0598(18) 0.0445(18) 0.0018(15) -0.0023(15) 0.0073(14)
C5 0.036(2) 0.041(2) 0.047(3) -0.0008(19) -0.004(2) 0.0038(17)
O2 0.048(2) 0.074(2) 0.0437(18) 0.0010(17) -0.0052(16) -0.0038(16)
C7 0.037(2) 0.038(2) 0.046(3) 0.0006(19) -0.002(2) 0.0043(17)
C6 0.035(2) 0.044(2) 0.047(3) -0.0007(19) 0.000(2) -0.0042(17)
C4 0.037(2) 0.038(2) 0.056(3) 0.0026(19) 0.005(2) 0.0026(18)
C8 0.037(2) 0.046(2) 0.059(3) -0.002(2) -0.008(2) 0.0018(18)
N8 0.047(2) 0.055(2) 0.047(2) 0.0001(18) -0.006(2) 0.0079(18)
C3 0.051(3) 0.050(3) 0.073(4) 0.013(3) 0.019(3) 0.009(2)
C12 0.048(3) 0.053(2) 0.057(3) -0.007(2) -0.002(2) 0.003(2)
O4 0.059(2) 0.078(2) 0.054(2) 0.0053(19) -0.0057(18) 0.0331(19)
C9 0.032(2) 0.043(2) 0.083(4) 0.005(2) 0.000(2) -0.0053(18)
C10 0.041(2) 0.048(2) 0.044(2) -0.009(2) -0.006(2) 0.0072(19)
C11 0.040(2) 0.044(2) 0.047(2) -0.009(2) -0.009(2) 0.0077(18)
C1 0.069(4) 0.068(3) 0.046(3) 0.007(2) 0.000(3) 0.010(3)
C2 0.069(4) 0.073(4) 0.049(3) 0.013(3) 0.012(3) 0.010(3)
C15 0.058(3) 0.062(3) 0.050(3) 0.006(2) -0.007(2) 0.005(2)
O1 0.091(4) 0.129(4) 0.052(2) 0.001(2) -0.023(2) -0.002(3)
C13 0.051(3) 0.068(3) 0.069(4) -0.004(3) 0.011(3) -0.001(3)
C14 0.064(3) 0.059(3) 0.053(3) 0.001(3) 0.004(3) -0.003(3)

_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
O3 C7 1.394(5) . ?
O3 C10 1.360(5) . ?
C5 O2 1.379(6) . ?
C5 C6 1.375(6) . ?
C5 C4 1.387(7) . ?
O2 C1 1.384(6) . ?
C7 C6 1.378(6) . ?
C7 C8 1.378(6) . ?
C4 C3 1.437(7) . ?
C4 C9 1.396(7) . ?
C8 C9 1.370(7) . ?
N8 C11 1.332(6) . ?
N8 C15 1.336(6) . ?
C3 C2 1.336(8) . ?
C12 C11 1.384(7) . ?
C12 C13 1.377(8) . ?
O4 C10 1.189(5) . ?
C10 C11 1.483(7) . ?
C1 C2 1.438(8) . ?
C1 O1 1.204(7) . ?
C15 C14 1.378(8) . ?
C13 C14 1.364(8) . ?

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
C10 O3 C7 117.7(3) . . ?
O2 C5 C4 121.3(4) . . ?
C6 C5 O2 116.2(4) . . ?
C6 C5 C4 122.5(4) . . ?
C5 O2 C1 122.0(4) . . ?
C6 C7 O3 120.9(4) . . ?
C6 C7 C8 122.1(4) . . ?
C8 C7 O3 116.9(4) . . ?
C5 C6 C7 117.6(4) . . ?
C5 C4 C3 117.5(4) . . ?
C5 C4 C9 117.7(4) . . ?
C9 C4 C3 124.7(4) . . ?
C9 C8 C7 119.1(4) . . ?
C11 N8 C15 116.7(4) . . ?
C2 C3 C4 120.4(5) . . ?
C13 C12 C11 118.1(5) . . ?
C8 C9 C4 121.0(4) . . ?
O3 C10 C11 112.6(4) . . ?
O4 C10 O3 122.8(4) . . ?
O4 C10 C11 124.5(4) . . ?
N8 C11 C12 123.5(5) . . ?
N8 C11 C10 118.8(4) . . ?
C12 C11 C10 117.7(4) . . ?
O2 C1 C2 116.3(5) . . ?
O1 C1 O2 116.6(5) . . ?
O1 C1 C2 127.2(5) . . ?
C3 C2 C1 122.4(5) . . ?
N8 C15 C14 123.8(5) . . ?
C14 C13 C12 119.6(5) . . ?
C13 C14 C15 118.3(5) . . ?

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 C7 C6 C5 -175.8(4) . . . . ?
O3 C7 C8 C9 175.5(4) . . . . ?
O3 C10 C11 N8 13.9(6) . . . . ?
O3 C10 C11 C12 -166.4(4) . . . . ?
C5 O2 C1 C2 -0.8(7) . . . . ?
C5 O2 C1 O1 178.5(5) . . . . ?
C5 C4 C3 C2 1.1(7) . . . . ?
C5 C4 C9 C8 -0.2(6) . . . . ?
O2 C5 C6 C7 -179.7(4) . . . . ?
O2 C5 C4 C3 -0.5(6) . . . . ?
O2 C5 C4 C9 179.4(4) . . . . ?
O2 C1 C2 C3 1.4(8) . . . . ?
C7 O3 C10 O4 -4.4(6) . . . . ?
C7 O3 C10 C11 175.6(3) . . . . ?
C7 C8 C9 C4 0.9(7) . . . . ?
C6 C5 O2 C1 -179.8(4) . . . . ?
C6 C5 C4 C3 179.7(4) . . . . ?
C6 C5 C4 C9 -0.4(6) . . . . ?
C6 C7 C8 C9 -1.2(7) . . . . ?
C4 C5 O2 C1 0.4(6) . . . . ?
C4 C5 C6 C7 0.1(6) . . . . ?
C4 C3 C2 C1 -1.6(8) . . . . ?
C8 C7 C6 C5 0.7(6) . . . . ?
N8 C15 C14 C13 -0.9(8) . . . . ?
C3 C4 C9 C8 179.8(4) . . . . ?
C12 C13 C14 C15 0.5(8) . . . . ?
O4 C10 C11 N8 -166.1(5) . . . . ?
O4 C10 C11 C12 13.6(7) . . . . ?
C9 C4 C3 C2 -178.8(5) . . . . ?
C10 O3 C7 C6 -55.2(5) . . . . ?
C10 O3 C7 C8 128.2(4) . . . . ?
C11 N8 C15 C14 1.1(7) . . . . ?
C11 C12 C13 C14 -0.5(8) . . . . ?
C15 N8 C11 C12 -1.0(6) . . . . ?
C15 N8 C11 C10 178.6(4) . . . . ?
O1 C1 C2 C3 -177.8(6) . . . . ?
C13 C12 C11 N8 0.7(7) . . . . ?
C13 C12 C11 C10 -178.9(5) . . . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_database_code_depnum_ccdc_archive 'CCDC 999735'
