# 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
#  on your local computer system.
# 
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#  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.
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data_L

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H13 N3 O'
_chemical_formula_sum            'C17 H13 N3 O'

_chemical_formula_weight         275.30

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   P21/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                   17.916(5)
_cell_length_b                   4.6430(12)
_cell_length_c                   20.248(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.13(3)
_cell_angle_gamma                90.00
_cell_volume                     1394.2(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.40

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576.0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3836
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.41
_diffrn_reflns_theta_max         28.97
_reflns_number_total             3664
_reflns_number_gt                2136
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0100P)²+0.6710P] 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         2264
_refine_ls_number_parameters     123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1839
_refine_ls_R_factor_gt           0.0969
_refine_ls_wR_factor_ref         0.1715
_refine_ls_wR_factor_gt          0.1463
_refine_ls_goodness_of_fit_ref   1.362
_refine_ls_restrained_S_all      1.362
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.002

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 0.3368(3) 0.8468(11) 0.0315(3) 0.0897(16) Uani 1 1 d . . .
N3 N 0.3165(5) 0.0451(12) 0.2901(5) 0.118(2) Uani 1 1 d . . .
N2 N 0.2844(3) 0.3744(10) 0.1595(3) 0.0749(16) Uani 1 1 d . . .
N1 N 0.2797(4) 0.5534(10) 0.1014(3) 0.0746(16) Uani 1 1 d . . .
C14 C 0.4644(4) -0.0076(13) 0.3197(5) 0.075(2) Uani 1 1 d . . .
H14 H 0.5069 0.0348 0.3086 0.090 Uiso 1 1 calc R . .
C17 C 0.3410(5) -0.1345(14) 0.3548(5) 0.094(2) Uani 1 1 d . . .
H17 H 0.2999 -0.1780 0.3677 0.113 Uiso 1 1 calc R . .
C16 C 0.4260(5) -0.2440(14) 0.3985(5) 0.114(3) Uani 1 1 d . . .
H16 H 0.4441 -0.3653 0.4416 0.137 Uiso 1 1 calc R . .
C11 C 0.2002(4) 0.6562(11) 0.0507(4) 0.0668(17) Uani 1 1 d . . .
H11 H 0.1532 0.6022 0.0552 0.080 Uiso 1 1 calc R . .
C13 C 0.3854(4) 0.0982(12) 0.2769(4) 0.0705(18) Uani 1 1 d . . .
C4 C 0.1533(5) 1.2590(12) -0.1264(4) 0.079(2) Uani 1 1 d . . .
H4 H 0.1451 1.3974 -0.1631 0.095 Uiso 1 1 calc R . .
C15 C 0.4847(5) -0.1714(18) 0.3777(6) 0.128(4) Uani 1 1 d . . .
H15 H 0.5427 -0.2469 0.4080 0.154 Uiso 1 1 calc R . .
C5 C -0.0080(5) 1.2876(12) -0.1783(4) 0.0792(19) Uani 1 1 d . . .
H5 H -0.0165 1.4243 -0.2155 0.095 Uiso 1 1 calc R . .
C2 C 0.2511(5) 0.9448(12) -0.0182(4) 0.072(2) Uani 1 1 d . . .
C1 C 0.1812(4) 0.8499(10) -0.0122(4) 0.0568(15) Uani 1 1 d . . .
C9 C 0.0932(4) 0.9634(10) -0.0669(4) 0.0566(15) Uani 1 1 d . . .
C12 C 0.3645(4) 0.2819(12) 0.2108(4) 0.076(2) Uani 1 1 d . . .
H12 H 0.4108 0.3350 0.2053 0.092 Uiso 1 1 calc R . .
C7 C -0.0667(5) 0.9901(14) -0.1214(5) 0.085(2) Uani 1 1 d . . .
H7 H -0.1156 0.9260 -0.1211 0.102 Uiso 1 1 calc R . .
C3 C 0.2357(5) 1.1429(13) -0.0753(5) 0.082(2) Uani 1 1 d . . .
H3 H 0.2833 1.1982 -0.0788 0.098 Uiso 1 1 calc R . .
C10 C 0.0792(4) 1.1688(11) -0.1238(4) 0.0667(18) Uani 1 1 d . . .
C8 C 0.0178(4) 0.8759(12) -0.0679(4) 0.078(2) Uani 1 1 d . . .
H8 H 0.0248 0.7375 -0.0316 0.094 Uiso 1 1 calc R . .
C6 C -0.0794(5) 1.2001(14) -0.1759(5) 0.089(2) Uani 1 1 d . . .
H6 H -0.1362 1.2806 -0.2104 0.106 Uiso 1 1 calc R . .
H1O H 0.332(6) 0.714(16) 0.056(6) 0.17(4) 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 0.076(3) 0.110(4) 0.096(5) 0.010(3) 0.056(4) -0.003(3)
N3 0.139(6) 0.125(5) 0.124(8) 0.011(4) 0.095(6) -0.005(4)
N2 0.068(4) 0.096(4) 0.062(5) 0.011(3) 0.037(4) 0.002(3)
N1 0.084(4) 0.081(3) 0.075(5) 0.016(3) 0.055(5) 0.005(3)
C14 0.047(4) 0.102(5) 0.077(7) 0.044(4) 0.036(5) 0.028(3)
C17 0.108(6) 0.110(5) 0.093(7) 0.026(5) 0.073(6) 0.016(4)
C16 0.113(6) 0.109(5) 0.111(9) 0.062(6) 0.058(8) 0.039(5)
C11 0.071(4) 0.070(4) 0.065(6) 0.002(3) 0.041(5) 0.003(3)
C13 0.067(4) 0.075(4) 0.074(6) 0.007(4) 0.043(5) 0.000(3)
C4 0.107(6) 0.073(4) 0.066(6) 0.013(4) 0.054(6) -0.002(4)
C15 0.059(5) 0.169(8) 0.138(12) 0.031(7) 0.043(8) 0.032(5)
C5 0.101(5) 0.072(4) 0.061(6) -0.002(4) 0.043(6) 0.004(4)
C2 0.081(5) 0.067(4) 0.079(7) 0.006(4) 0.052(6) 0.001(3)
C1 0.060(4) 0.060(3) 0.048(5) -0.001(3) 0.028(4) -0.003(3)
C9 0.073(4) 0.056(3) 0.046(4) -0.007(3) 0.037(4) -0.005(3)
C12 0.069(5) 0.093(4) 0.079(7) 0.009(4) 0.048(5) -0.002(4)
C7 0.084(5) 0.099(5) 0.082(7) -0.010(4) 0.052(6) -0.003(4)
C3 0.094(5) 0.089(5) 0.077(7) 0.003(4) 0.058(6) -0.010(4)
C10 0.074(4) 0.068(4) 0.056(6) -0.011(3) 0.035(5) -0.007(3)
C8 0.087(5) 0.079(4) 0.076(7) 0.000(4) 0.050(6) 0.002(4)
C6 0.090(5) 0.094(5) 0.071(7) -0.023(4) 0.038(6) -0.002(4)

_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 C2 1.357(7) . ?
O1 H1O 0.82(8) . ?
N3 C17 1.400(9) . ?
N3 C13 1.424(6) . ?
N2 C12 1.284(7) . ?
N2 N1 1.404(6) . ?
N1 C11 1.293(7) . ?
C14 C15 1.269(9) . ?
C14 C13 1.271(8) . ?
C14 H14 0.9300 . ?
C17 C16 1.360(8) . ?
C17 H17 0.9300 . ?
C16 C15 1.377(8) . ?
C16 H16 0.9300 . ?
C11 C1 1.435(7) . ?
C11 H11 0.9300 . ?
C13 C12 1.448(8) . ?
C4 C3 1.352(8) . ?
C4 C10 1.421(6) . ?
C4 H4 0.9300 . ?
C15 H15 0.9300 . ?
C5 C6 1.369(7) . ?
C5 C10 1.424(8) . ?
C5 H5 0.9300 . ?
C2 C3 1.378(8) . ?
C2 C1 1.397(6) . ?
C1 C9 1.425(7) . ?
C9 C8 1.401(6) . ?
C9 C10 1.404(7) . ?
C12 H12 0.9300 . ?
C7 C8 1.380(8) . ?
C7 C6 1.391(8) . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C8 H8 0.9300 . ?
C6 H6 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
C2 O1 H1O 104(6) . . ?
C17 N3 C13 115.4(6) . . ?
C12 N2 N1 113.0(5) . . ?
C11 N1 N2 113.9(5) . . ?
C15 C14 C13 119.6(6) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C17 N3 118.8(6) . . ?
C16 C17 H17 120.6 . . ?
N3 C17 H17 120.6 . . ?
C17 C16 C15 118.5(7) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
N1 C11 C1 122.9(5) . . ?
N1 C11 H11 118.6 . . ?
C1 C11 H11 118.6 . . ?
C14 C13 N3 123.7(6) . . ?
C14 C13 C12 118.0(6) . . ?
N3 C13 C12 118.2(6) . . ?
C3 C4 C10 119.8(6) . . ?
C3 C4 H4 120.1 . . ?
C10 C4 H4 120.1 . . ?
C14 C15 C16 124.0(7) . . ?
C14 C15 H15 118.0 . . ?
C16 C15 H15 118.0 . . ?
C6 C5 C10 119.9(6) . . ?
C6 C5 H5 120.1 . . ?
C10 C5 H5 120.1 . . ?
O1 C2 C3 117.2(6) . . ?
O1 C2 C1 121.7(6) . . ?
C3 C2 C1 121.1(6) . . ?
C2 C1 C9 118.0(5) . . ?
C2 C1 C11 119.9(5) . . ?
C9 C1 C11 122.0(5) . . ?
C8 C9 C10 117.2(6) . . ?
C8 C9 C1 122.7(5) . . ?
C10 C9 C1 120.0(5) . . ?
N2 C12 C13 122.5(5) . . ?
N2 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
C8 C7 C6 120.8(6) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C4 C3 C2 121.8(6) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C9 C10 C4 119.2(6) . . ?
C9 C10 C5 120.9(5) . . ?
C4 C10 C5 119.9(6) . . ?
C7 C8 C9 121.6(6) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C5 C6 C7 119.7(7) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        28.97
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 1000232'
