# 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
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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.
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data_un

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 N1 O3'
_chemical_formula_weight         253.25

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   9.890(2)
_cell_length_b                   7.3000(15)
_cell_length_c                   32.941(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2378.2(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    0.100
_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      173(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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22472
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         31.29
_reflns_number_total             3659
_reflns_number_gt                3154
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.2000P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3659
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.2808
_refine_ls_wR_factor_gt          0.2655
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.130
_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
O3 O 0.10386(14) 0.3517(2) 0.05189(4) 0.0253(4) Uani 1 1 d . . .
O2 O 0.67793(16) 0.4990(3) 0.11728(4) 0.0464(5) Uani 1 1 d . . .
O1 O 0.73009(17) 0.3951(3) 0.05824(5) 0.0441(5) Uani 1 1 d . . .
N2 N 0.64708(17) 0.4364(3) 0.08430(5) 0.0291(4) Uani 1 1 d . . .
C2 C 0.08833(17) 0.6007(2) 0.24134(5) 0.0193(4) Uani 1 1 d . . .
C3 C 0.12528(17) 0.5072(2) 0.15873(5) 0.0182(4) Uani 1 1 d . . .
C4 C 0.20170(17) 0.5032(2) 0.22863(5) 0.0200(4) Uani 1 1 d . . .
H4 H 0.2680 0.4683 0.2480 0.024 Uiso 1 1 calc R . .
C5 C 0.01089(17) 0.6044(2) 0.17119(5) 0.0202(4) Uani 1 1 d . . .
H5 H -0.0554 0.6392 0.1518 0.024 Uiso 1 1 calc R . .
C6 C -0.00654(18) 0.6504(2) 0.21178(5) 0.0209(4) Uani 1 1 d . . .
H6 H -0.0847 0.7173 0.2197 0.025 Uiso 1 1 calc R . .
C7 C 0.24023(19) 0.3633(2) 0.05630(5) 0.0223(4) Uani 1 1 d . . .
C8 C 0.21981(17) 0.4559(2) 0.18807(5) 0.0195(4) Uani 1 1 d . . .
H8 H 0.2974 0.3879 0.1803 0.023 Uiso 1 1 calc R . .
C9 C 0.41020(17) 0.4532(2) 0.10470(5) 0.0204(4) Uani 1 1 d . . .
H9 H 0.4372 0.5000 0.1304 0.025 Uiso 1 1 calc R . .
C10 C 0.14624(18) 0.4520(2) 0.11624(5) 0.0200(4) Uani 1 1 d . . .
C11 C 0.27434(18) 0.4266(2) 0.09515(5) 0.0194(4) Uani 1 1 d . . .
C12 C 0.50393(18) 0.4087(3) 0.07519(5) 0.0222(4) Uani 1 1 d . . .
C13 C 0.0694(2) 0.6484(3) 0.28539(5) 0.0237(4) Uani 1 1 d . . .
H13A H -0.0152 0.7165 0.2888 0.036 Uiso 1 1 calc R . .
H13B H 0.1454 0.7240 0.2946 0.036 Uiso 1 1 calc R . .
H13C H 0.0658 0.5357 0.3015 0.036 Uiso 1 1 calc R . .
C14 C 0.4690(2) 0.3392(3) 0.03694(5) 0.0257(4) Uani 1 1 d . . .
H14 H 0.5377 0.3076 0.0181 0.031 Uiso 1 1 calc R . .
C15 C 0.04972(19) 0.4069(3) 0.08870(5) 0.0233(4) Uani 1 1 d . . .
H15 H -0.0446 0.4126 0.0941 0.028 Uiso 1 1 calc R . .
C1 C 0.33528(19) 0.3168(3) 0.02676(5) 0.0254(4) Uani 1 1 d . . .
H1 H 0.3089 0.2718 0.0009 0.030 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 0.0230(7) 0.0327(7) 0.0203(6) -0.0031(5) -0.0015(5) -0.0026(5)
O2 0.0230(8) 0.0874(14) 0.0288(8) -0.0212(8) -0.0004(6) -0.0061(9)
O1 0.0243(8) 0.0776(14) 0.0305(8) -0.0134(8) 0.0075(6) 0.0037(8)
N2 0.0205(8) 0.0427(10) 0.0241(8) -0.0026(7) 0.0033(6) 0.0023(7)
C2 0.0205(9) 0.0173(7) 0.0199(7) -0.0006(6) 0.0039(6) -0.0022(6)
C3 0.0180(8) 0.0176(7) 0.0189(7) 0.0005(6) 0.0011(6) -0.0012(6)
C4 0.0205(8) 0.0189(7) 0.0205(7) -0.0006(6) -0.0002(6) -0.0003(6)
C5 0.0181(8) 0.0188(8) 0.0238(8) 0.0031(6) -0.0004(6) -0.0018(6)
C6 0.0193(8) 0.0179(8) 0.0255(8) 0.0021(6) 0.0041(6) 0.0005(6)
C7 0.0224(9) 0.0236(8) 0.0209(8) -0.0016(6) -0.0034(6) -0.0005(6)
C8 0.0183(8) 0.0192(8) 0.0208(7) -0.0010(6) 0.0017(6) 0.0008(6)
C9 0.0216(9) 0.0222(8) 0.0175(7) -0.0005(6) 0.0008(6) -0.0011(6)
C10 0.0178(8) 0.0210(8) 0.0212(8) 0.0002(6) -0.0006(6) -0.0002(6)
C11 0.0218(9) 0.0189(7) 0.0175(7) -0.0008(6) 0.0002(6) -0.0005(6)
C12 0.0181(9) 0.0287(9) 0.0198(8) 0.0006(6) 0.0010(6) 0.0011(6)
C13 0.0272(9) 0.0222(8) 0.0217(8) -0.0006(6) 0.0039(6) 0.0002(6)
C14 0.0268(10) 0.0308(10) 0.0196(8) -0.0034(7) 0.0035(6) 0.0025(7)
C15 0.0205(9) 0.0283(9) 0.0213(8) -0.0002(6) -0.0008(6) -0.0008(6)
C1 0.0291(10) 0.0298(9) 0.0171(7) -0.0028(6) -0.0016(6) 0.0001(7)

_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 1.359(2) . ?
O3 C15 1.386(2) . ?
O2 N2 1.218(2) . ?
O1 N2 1.225(2) . ?
N2 C12 1.461(2) . ?
C2 C4 1.392(2) . ?
C2 C6 1.400(2) . ?
C2 C13 1.504(2) . ?
C3 C8 1.396(2) . ?
C3 C5 1.397(2) . ?
C3 C10 1.471(2) . ?
C4 C8 1.392(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C1 1.395(3) . ?
C7 C11 1.402(2) . ?
C8 H8 0.9500 . ?
C9 C12 1.382(2) . ?
C9 C11 1.394(2) . ?
C9 H9 0.9500 . ?
C10 C15 1.357(2) . ?
C10 C11 1.457(2) . ?
C12 C14 1.402(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C1 1.374(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C1 H1 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
C7 O3 C15 105.76(14) . . ?
O2 N2 O1 123.34(18) . . ?
O2 N2 C12 118.55(16) . . ?
O1 N2 C12 118.12(16) . . ?
C4 C2 C6 117.59(16) . . ?
C4 C2 C13 120.56(16) . . ?
C6 C2 C13 121.85(16) . . ?
C8 C3 C5 118.36(15) . . ?
C8 C3 C10 119.41(15) . . ?
C5 C3 C10 122.19(16) . . ?
C8 C4 C2 121.27(16) . . ?
C8 C4 H4 119.4 . . ?
C2 C4 H4 119.4 . . ?
C6 C5 C3 120.41(16) . . ?
C6 C5 H5 119.8 . . ?
C3 C5 H5 119.8 . . ?
C5 C6 C2 121.55(16) . . ?
C5 C6 H6 119.2 . . ?
C2 C6 H6 119.2 . . ?
O3 C7 C1 125.38(16) . . ?
O3 C7 C11 110.91(15) . . ?
C1 C7 C11 123.70(17) . . ?
C4 C8 C3 120.80(16) . . ?
C4 C8 H8 119.6 . . ?
C3 C8 H8 119.6 . . ?
C12 C9 C11 117.08(16) . . ?
C12 C9 H9 121.5 . . ?
C11 C9 H9 121.5 . . ?
C15 C10 C11 105.19(15) . . ?
C15 C10 C3 127.09(17) . . ?
C11 C10 C3 127.68(15) . . ?
C9 C11 C7 118.95(16) . . ?
C9 C11 C10 135.48(15) . . ?
C7 C11 C10 105.56(15) . . ?
C9 C12 C14 123.49(17) . . ?
C9 C12 N2 118.23(16) . . ?
C14 C12 N2 118.28(16) . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C14 C12 120.01(17) . . ?
C1 C14 H14 120.0 . . ?
C12 C14 H14 120.0 . . ?
C10 C15 O3 112.57(16) . . ?
C10 C15 H15 123.7 . . ?
O3 C15 H15 123.7 . . ?
C14 C1 C7 116.70(16) . . ?
C14 C1 H1 121.7 . . ?
C7 C1 H1 121.7 . . ?

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
C6 C2 C4 C8 -0.4(3) . . . . ?
C13 C2 C4 C8 179.14(16) . . . . ?
C8 C3 C5 C6 0.9(3) . . . . ?
C10 C3 C5 C6 178.59(16) . . . . ?
C3 C5 C6 C2 -0.4(3) . . . . ?
C4 C2 C6 C5 0.2(3) . . . . ?
C13 C2 C6 C5 -179.35(16) . . . . ?
C15 O3 C7 C1 178.60(18) . . . . ?
C15 O3 C7 C11 -0.54(19) . . . . ?
C2 C4 C8 C3 0.9(3) . . . . ?
C5 C3 C8 C4 -1.1(3) . . . . ?
C10 C3 C8 C4 -178.88(16) . . . . ?
C8 C3 C10 C15 145.47(19) . . . . ?
C5 C3 C10 C15 -32.2(3) . . . . ?
C8 C3 C10 C11 -31.7(3) . . . . ?
C5 C3 C10 C11 150.61(18) . . . . ?
C12 C9 C11 C7 -2.2(3) . . . . ?
C12 C9 C11 C10 179.31(19) . . . . ?
O3 C7 C11 C9 -177.78(15) . . . . ?
C1 C7 C11 C9 3.1(3) . . . . ?
O3 C7 C11 C10 1.11(19) . . . . ?
C1 C7 C11 C10 -178.05(17) . . . . ?
C15 C10 C11 C9 177.4(2) . . . . ?
C3 C10 C11 C9 -5.0(3) . . . . ?
C15 C10 C11 C7 -1.2(2) . . . . ?
C3 C10 C11 C7 176.44(17) . . . . ?
C11 C9 C12 C14 -0.1(3) . . . . ?
C11 C9 C12 N2 179.64(16) . . . . ?
O2 N2 C12 C9 -0.7(3) . . . . ?
O1 N2 C12 C9 179.28(19) . . . . ?
O2 N2 C12 C14 179.0(2) . . . . ?
O1 N2 C12 C14 -1.0(3) . . . . ?
C9 C12 C14 C1 1.8(3) . . . . ?
N2 C12 C14 C1 -177.95(18) . . . . ?
C11 C10 C15 O3 1.0(2) . . . . ?
C3 C10 C15 O3 -176.71(16) . . . . ?
C7 O3 C15 C10 -0.3(2) . . . . ?
C12 C14 C1 C7 -1.0(3) . . . . ?
O3 C7 C1 C14 179.59(18) . . . . ?
C11 C7 C1 C14 -1.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.940
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.074

_database_code_depnum_ccdc_archive 'CCDC 1005517'
