# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_xb6298

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H9 N O2'
_chemical_formula_weight         223.22

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)/n

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

_cell_length_a                   13.366(4)
_cell_length_b                   3.9100(12)
_cell_length_c                   20.520(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.020(5)
_cell_angle_gamma                90.00
_cell_volume                     1068.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1253
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      23.79

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9666
_exptl_absorpt_correction_T_max  0.9871
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4978
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         25.09
_reflns_number_total             1899
_reflns_number_gt                1557
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.1700P)^2^+0.5915P] where P=(Fo^2^+2Fc^2^)/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         1899
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.2579
_refine_ls_wR_factor_gt          0.2264
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
N1 N 0.59144(17) 0.9227(6) 0.72661(12) 0.0450(7) Uani 1 1 d . . .
O1 O 0.41583(17) 1.4226(7) 0.58822(11) 0.0703(8) Uani 1 1 d . . .
O2 O 0.44241(14) 1.2026(6) 0.68706(9) 0.0499(6) Uani 1 1 d . . .
C1 C 0.6279(2) 0.9660(7) 0.66495(14) 0.0414(7) Uani 1 1 d . . .
C2 C 0.7235(2) 0.8440(8) 0.65447(15) 0.0510(8) Uani 1 1 d . . .
H2 H 0.7631 0.7389 0.6883 0.061 Uiso 1 1 calc R . .
C3 C 0.7588(2) 0.8807(9) 0.59370(16) 0.0532(9) Uani 1 1 d . . .
H3 H 0.8223 0.7989 0.5868 0.064 Uiso 1 1 calc R . .
C4 C 0.7015(2) 1.0366(9) 0.54294(16) 0.0553(9) Uani 1 1 d . . .
H4 H 0.7264 1.0570 0.5022 0.066 Uiso 1 1 calc R . .
C5 C 0.6080(2) 1.1619(8) 0.55252(15) 0.0520(8) Uani 1 1 d . . .
H5 H 0.5696 1.2690 0.5185 0.062 Uiso 1 1 calc R . .
C6 C 0.5710(2) 1.1276(7) 0.61351(14) 0.0419(7) Uani 1 1 d . . .
C7 C 0.4725(2) 1.2628(8) 0.62524(14) 0.0476(8) Uani 1 1 d . . .
C8 C 0.5040(2) 1.0365(7) 0.73433(13) 0.0419(7) Uani 1 1 d . . .
C9 C 0.4568(2) 1.0032(8) 0.79608(15) 0.0466(8) Uani 1 1 d . . .
C10 C 0.3593(2) 1.1123(9) 0.80185(17) 0.0559(9) Uani 1 1 d . . .
H10 H 0.3218 1.2079 0.7661 0.067 Uiso 1 1 calc R . .
C11 C 0.3177(3) 1.0783(10) 0.8613(2) 0.0703(11) Uani 1 1 d . . .
H11 H 0.2523 1.1508 0.8653 0.084 Uiso 1 1 calc R . .
C12 C 0.3733(3) 0.9380(11) 0.9138(2) 0.0736(11) Uani 1 1 d . . .
H12 H 0.3451 0.9152 0.9535 0.088 Uiso 1 1 calc R . .
C13 C 0.4702(3) 0.8306(10) 0.90857(17) 0.0679(10) Uani 1 1 d . . .
H13 H 0.5075 0.7383 0.9447 0.081 Uiso 1 1 calc R . .
C14 C 0.5121(3) 0.8595(9) 0.84980(15) 0.0544(8) Uani 1 1 d . . .
H14 H 0.5773 0.7831 0.8461 0.065 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
N1 0.0400(13) 0.0449(14) 0.0486(14) 0.0046(11) -0.0053(10) 0.0010(10)
O1 0.0517(13) 0.099(2) 0.0590(14) 0.0263(13) -0.0003(11) 0.0220(13)
O2 0.0399(11) 0.0612(14) 0.0478(12) 0.0081(10) -0.0009(9) 0.0071(9)
C1 0.0401(14) 0.0358(15) 0.0472(16) -0.0011(12) -0.0022(12) -0.0029(11)
C2 0.0420(15) 0.0514(18) 0.0578(19) -0.0023(14) -0.0067(14) 0.0042(13)
C3 0.0408(15) 0.0563(19) 0.063(2) -0.0098(15) 0.0046(14) -0.0001(13)
C4 0.0560(18) 0.061(2) 0.0499(18) -0.0070(15) 0.0096(14) -0.0043(15)
C5 0.0502(17) 0.0546(19) 0.0499(17) 0.0040(14) -0.0027(13) -0.0027(14)
C6 0.0402(14) 0.0389(15) 0.0454(16) 0.0005(12) -0.0034(12) -0.0041(12)
C7 0.0423(15) 0.0521(18) 0.0471(17) 0.0085(14) -0.0033(12) 0.0033(13)
C8 0.0404(14) 0.0390(15) 0.0446(16) 0.0011(12) -0.0058(12) -0.0029(11)
C9 0.0466(16) 0.0443(17) 0.0485(17) -0.0021(13) 0.0014(13) -0.0089(12)
C10 0.0466(16) 0.060(2) 0.061(2) -0.0001(16) 0.0021(14) -0.0054(14)
C11 0.058(2) 0.075(2) 0.082(3) -0.006(2) 0.0234(19) -0.0117(18)
C12 0.090(3) 0.072(3) 0.063(2) 0.0030(19) 0.028(2) -0.020(2)
C13 0.083(3) 0.066(2) 0.055(2) 0.0073(17) 0.0056(18) -0.0078(19)
C14 0.0575(18) 0.0552(19) 0.0502(18) 0.0028(14) 0.0021(14) -0.0034(15)

_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
N1 C8 1.274(4) . ?
N1 C1 1.405(4) . ?
O1 C7 1.200(3) . ?
O2 C8 1.379(3) . ?
O2 C7 1.384(4) . ?
C1 C6 1.397(4) . ?
C1 C2 1.399(4) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.458(4) . ?
C8 C9 1.470(4) . ?
C9 C10 1.386(4) . ?
C9 C14 1.391(4) . ?
C10 C11 1.390(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(5) . ?
C13 H13 0.9300 . ?
C14 H14 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
C8 N1 C1 117.6(2) . . ?
C8 O2 C7 121.4(2) . . ?
C6 C1 C2 118.9(3) . . ?
C6 C1 N1 121.8(3) . . ?
C2 C1 N1 119.4(3) . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 120.7(3) . . ?
C5 C6 C7 120.7(3) . . ?
C1 C6 C7 118.6(3) . . ?
O1 C7 O2 116.8(3) . . ?
O1 C7 C6 127.8(3) . . ?
O2 C7 C6 115.4(2) . . ?
N1 C8 O2 125.1(3) . . ?
N1 C8 C9 123.0(3) . . ?
O2 C8 C9 111.9(2) . . ?
C10 C9 C14 119.7(3) . . ?
C10 C9 C8 121.6(3) . . ?
C14 C9 C8 118.7(3) . . ?
C9 C10 C11 119.8(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 120.1(4) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?

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
C8 N1 C1 C6 0.0(4) . . . . ?
C8 N1 C1 C2 -179.9(3) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
N1 C1 C2 C3 178.9(3) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C4 C5 C6 C1 -0.2(5) . . . . ?
C4 C5 C6 C7 179.1(3) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
N1 C1 C6 C5 -178.8(3) . . . . ?
C2 C1 C6 C7 -178.3(3) . . . . ?
N1 C1 C6 C7 1.8(4) . . . . ?
C8 O2 C7 O1 -176.7(3) . . . . ?
C8 O2 C7 C6 2.2(4) . . . . ?
C5 C6 C7 O1 -3.3(5) . . . . ?
C1 C6 C7 O1 176.0(3) . . . . ?
C5 C6 C7 O2 177.8(3) . . . . ?
C1 C6 C7 O2 -2.8(4) . . . . ?
C1 N1 C8 O2 -0.7(4) . . . . ?
C1 N1 C8 C9 179.1(2) . . . . ?
C7 O2 C8 N1 -0.5(4) . . . . ?
C7 O2 C8 C9 179.7(2) . . . . ?
N1 C8 C9 C10 -176.3(3) . . . . ?
O2 C8 C9 C10 3.6(4) . . . . ?
N1 C8 C9 C14 4.0(4) . . . . ?
O2 C8 C9 C14 -176.1(3) . . . . ?
C14 C9 C10 C11 0.2(5) . . . . ?
C8 C9 C10 C11 -179.5(3) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
C10 C11 C12 C13 0.2(6) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
C12 C13 C14 C9 1.1(5) . . . . ?
C10 C9 C14 C13 -0.8(5) . . . . ?
C8 C9 C14 C13 178.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.108
_database_code_depnum_ccdc_archive 'CCDC 942843'