# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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.
#
data_kb

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N O2'
_chemical_formula_weight         275.29

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)/c

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

_cell_length_a                   12.371(4)
_cell_length_b                   7.489(2)
_cell_length_c                   15.557(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.019(9)
_cell_angle_gamma                90.00
_cell_volume                     1336.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(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    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16007
_diffrn_reflns_av_R_equivalents  0.1136
_diffrn_reflns_av_sigmaI/netI    0.0766
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2479
_reflns_number_gt                1138
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.1000P)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         2479
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1552
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1728
_refine_ls_wR_factor_gt          0.1326
_refine_ls_goodness_of_fit_ref   0.827
_refine_ls_restrained_S_all      0.827
_refine_ls_shift/su_max          0.001
_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
O11 O 0.6970(2) 0.2367(4) 0.05167(16) 0.0877(10) Uani 1 1 d . . .
O12 O 0.88280(19) 0.4083(3) 0.41293(13) 0.0466(6) Uani 1 1 d . . .
H1O H 0.894(3) 0.507(4) 0.3886(19) 0.050 Uiso 1 1 d . . .
N11 N 1.0491(3) 0.2003(3) 0.17319(18) 0.0501(7) Uani 1 1 d . . .
C10 C 0.7375(3) 0.2586(4) 0.1345(2) 0.0526(9) Uani 1 1 d . . .
C11 C 0.8637(3) 0.2420(4) 0.18844(18) 0.0393(7) Uani 1 1 d . . .
C12 C 0.9137(3) 0.2603(4) 0.28343(19) 0.0423(8) Uani 1 1 d . . .
C13 C 0.8379(3) 0.2780(4) 0.34112(19) 0.0435(8) Uani 1 1 d . . .
C14 C 0.7106(3) 0.3247(4) 0.2818(2) 0.0446(8) Uani 1 1 d . . .
C15 C 0.6634(3) 0.3129(4) 0.1856(2) 0.0490(8) Uani 1 1 d . . .
C16 C 0.5479(3) 0.3587(5) 0.1362(3) 0.0669(10) Uani 1 1 d . . .
H16 H 0.5170 0.3502 0.0719 0.080 Uiso 1 1 calc R . .
C17 C 0.4796(3) 0.4167(5) 0.1826(3) 0.0790(12) Uani 1 1 d . . .
H17 H 0.4027 0.4504 0.1497 0.095 Uiso 1 1 calc R . .
C18 C 0.5253(3) 0.4251(5) 0.2786(3) 0.0732(12) Uani 1 1 d . . .
H18 H 0.4784 0.4617 0.3101 0.088 Uiso 1 1 calc R . .
C19 C 0.6389(3) 0.3799(4) 0.3272(2) 0.0561(9) Uani 1 1 d . . .
H19 H 0.6686 0.3862 0.3916 0.067 Uiso 1 1 calc R . .
C110 C 0.8408(3) 0.1005(4) 0.3904(2) 0.0520(9) Uani 1 1 d . . .
H11A H 0.9200 0.0704 0.4278 0.078 Uiso 1 1 calc R . .
H11B H 0.8076 0.0084 0.3452 0.078 Uiso 1 1 calc R . .
H11C H 0.7964 0.1111 0.4293 0.078 Uiso 1 1 calc R . .
C21 C 1.1022(3) 0.2287(4) 0.2680(2) 0.0443(8) Uani 1 1 d . . .
C22 C 1.0396(3) 0.2516(4) 0.3266(2) 0.0428(8) Uani 1 1 d . . .
C23 C 1.1049(3) 0.2721(4) 0.4238(2) 0.0524(9) Uani 1 1 d . . .
H23 H 1.0662 0.2853 0.4644 0.063 Uiso 1 1 calc R . .
C24 C 1.2237(3) 0.2722(4) 0.4569(2) 0.0632(10) Uani 1 1 d . . .
H24 H 1.2656 0.2845 0.5203 0.076 Uiso 1 1 calc R . .
C25 C 1.2832(3) 0.2542(5) 0.3972(3) 0.0646(10) Uani 1 1 d . . .
H25 H 1.3642 0.2582 0.4206 0.078 Uiso 1 1 calc R . .
C26 C 1.2236(3) 0.2309(4) 0.3051(3) 0.0571(9) Uani 1 1 d . . .
H26 H 1.2644 0.2161 0.2661 0.069 Uiso 1 1 calc R . .
C27 C 0.9370(3) 0.2070(4) 0.1384(2) 0.0498(9) Uani 1 1 d . . .
H27 H 0.9007 0.1874 0.0749 0.060 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
O11 0.0738(19) 0.138(3) 0.0413(14) -0.0157(14) 0.0098(13) 0.0055(17)
O12 0.0642(15) 0.0469(14) 0.0355(11) -0.0098(10) 0.0265(10) -0.0101(12)
N11 0.061(2) 0.0465(17) 0.0492(16) -0.0006(12) 0.0280(15) 0.0036(14)
C10 0.055(2) 0.058(2) 0.0379(19) -0.0055(15) 0.0098(17) -0.0029(17)
C11 0.0463(19) 0.0437(18) 0.0283(15) -0.0029(13) 0.0142(14) -0.0023(15)
C12 0.055(2) 0.0333(17) 0.0398(17) 0.0011(13) 0.0187(15) -0.0022(15)
C13 0.061(2) 0.0412(18) 0.0354(16) -0.0064(13) 0.0259(15) -0.0069(16)
C14 0.047(2) 0.0407(18) 0.0457(19) -0.0039(15) 0.0166(16) -0.0023(15)
C15 0.049(2) 0.0459(19) 0.054(2) -0.0037(16) 0.0213(17) -0.0002(16)
C16 0.057(3) 0.068(3) 0.068(2) -0.001(2) 0.014(2) 0.004(2)
C17 0.046(2) 0.076(3) 0.102(3) -0.006(2) 0.012(2) 0.015(2)
C18 0.053(3) 0.076(3) 0.099(3) -0.011(2) 0.038(2) 0.004(2)
C19 0.055(2) 0.057(2) 0.061(2) -0.0046(17) 0.0271(19) 0.0035(18)
C110 0.064(2) 0.0445(19) 0.0493(19) 0.0047(15) 0.0236(17) -0.0064(17)
C21 0.052(2) 0.0361(18) 0.0479(19) 0.0018(14) 0.0221(16) 0.0051(15)
C22 0.044(2) 0.0338(17) 0.0466(18) 0.0002(13) 0.0128(16) 0.0011(14)
C23 0.053(2) 0.057(2) 0.0459(19) -0.0026(16) 0.0172(17) 0.0039(17)
C24 0.058(3) 0.068(3) 0.050(2) -0.0012(17) 0.0038(18) 0.0037(19)
C25 0.046(2) 0.070(3) 0.072(3) 0.0001(19) 0.016(2) 0.0069(18)
C26 0.057(3) 0.048(2) 0.070(2) -0.0011(17) 0.027(2) 0.0048(17)
C27 0.061(2) 0.051(2) 0.0368(18) -0.0004(14) 0.0171(17) 0.0027(17)

_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
O11 C10 1.206(3) . ?
O12 C13 1.430(3) . ?
N11 C27 1.287(4) . ?
N11 C21 1.388(4) . ?
C10 C11 1.475(4) . ?
C10 C15 1.478(4) . ?
C11 C12 1.378(4) . ?
C11 C27 1.424(4) . ?
C12 C22 1.448(4) . ?
C12 C13 1.527(4) . ?
C13 C110 1.529(4) . ?
C13 C14 1.538(4) . ?
C14 C15 1.390(4) . ?
C14 C19 1.389(4) . ?
C15 C16 1.388(4) . ?
C16 C17 1.372(5) . ?
C17 C18 1.386(5) . ?
C18 C19 1.365(4) . ?
C21 C26 1.392(4) . ?
C21 C22 1.410(4) . ?
C22 C23 1.431(4) . ?
C23 C24 1.363(5) . ?
C24 C25 1.391(5) . ?
C25 C26 1.354(5) . ?

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
C27 N11 C21 116.5(3) . . ?
O11 C10 C11 121.6(3) . . ?
O11 C10 C15 121.3(3) . . ?
C11 C10 C15 117.1(3) . . ?
C12 C11 C27 118.9(3) . . ?
C12 C11 C10 123.7(3) . . ?
C27 C11 C10 117.4(3) . . ?
C11 C12 C22 117.7(3) . . ?
C11 C12 C13 120.8(3) . . ?
C22 C12 C13 121.5(3) . . ?
O12 C13 C110 105.8(2) . . ?
O12 C13 C12 112.0(2) . . ?
C110 C13 C12 108.4(2) . . ?
O12 C13 C14 108.9(2) . . ?
C110 C13 C14 108.9(2) . . ?
C12 C13 C14 112.5(2) . . ?
C15 C14 C19 118.4(3) . . ?
C15 C14 C13 123.7(3) . . ?
C19 C14 C13 118.0(3) . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 C10 120.1(3) . . ?
C16 C15 C10 119.1(3) . . ?
C17 C16 C15 119.7(4) . . ?
C16 C17 C18 119.9(4) . . ?
C19 C18 C17 120.3(3) . . ?
C18 C19 C14 120.9(3) . . ?
N11 C21 C26 116.7(3) . . ?
N11 C21 C22 123.4(3) . . ?
C26 C21 C22 119.9(3) . . ?
C21 C22 C23 117.8(3) . . ?
C21 C22 C12 117.5(3) . . ?
C23 C22 C12 124.6(3) . . ?
C24 C23 C22 120.0(3) . . ?
C23 C24 C25 120.9(3) . . ?
C26 C25 C24 120.3(3) . . ?
C25 C26 C21 121.0(3) . . ?
N11 C27 C11 125.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 997846'
