# 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.
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data_c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 N O'
_chemical_formula_weight         159.18

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7404(15)
_cell_length_b                   8.6624(17)
_cell_length_c                   13.340(3)
_cell_angle_alpha                81.46(3)
_cell_angle_beta                 89.70(3)
_cell_angle_gamma                70.47(3)
_cell_volume                     832.7(3)
_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    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.083
_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            5809
_diffrn_reflns_av_R_equivalents  0.0874
_diffrn_reflns_av_sigmaI/netI    0.1680
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2896
_reflns_number_gt                1328
_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)+(0.1169P)²+1.5259P] 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         2896
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3106
_refine_ls_R_factor_gt           0.2092
_refine_ls_wR_factor_ref         0.4630
_refine_ls_wR_factor_gt          0.3973
_refine_ls_goodness_of_fit_ref   1.275
_refine_ls_restrained_S_all      1.275
_refine_ls_shift/su_max          0.194
_refine_ls_shift/su_mean         0.023

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 0.3577(11) 0.8624(10) 0.0933(6) 0.085(3) Uani 1 1 d . . .
O2 O 0.2374(12) 0.8228(10) 0.4050(6) 0.094(3) Uani 1 1 d . . .
N1 N 0.1966(12) 1.0719(10) 0.1687(6) 0.068(3) Uani 1 1 d . . .
N2 N 0.2461(13) 1.0797(12) 0.3886(7) 0.076(3) Uani 1 1 d . . .
C1 C 0.237(2) 1.0404(16) -0.1052(8) 0.094(4) Uani 1 1 d . . .
H1 H 0.3229 0.9341 -0.0975 0.113 Uiso 1 1 calc R . .
C2 C 0.171(3) 1.123(2) -0.2026(10) 0.119(6) Uani 1 1 d . . .
H2 H 0.2149 1.0754 -0.2598 0.142 Uiso 1 1 calc R . .
C3 C 0.040(2) 1.279(2) -0.2106(11) 0.108(5) Uani 1 1 d . . .
H3 H -0.0088 1.3344 -0.2749 0.130 Uiso 1 1 calc R . .
C4 C -0.023(2) 1.356(2) -0.1291(12) 0.124(6) Uani 1 1 d . . .
H4 H -0.1092 1.4625 -0.1383 0.149 Uiso 1 1 calc R . .
C5 C 0.0445(19) 1.273(2) -0.0303(10) 0.109(5) Uani 1 1 d . . .
H5 H 0.0041 1.3228 0.0268 0.131 Uiso 1 1 calc R . .
C6 C 0.1777(18) 1.1103(16) -0.0220(9) 0.080(4) Uani 1 1 d . . .
C7 C 0.2422(13) 1.0201(17) 0.0824(7) 0.061(3) Uani 1 1 d . . .
C8 C 0.2885(15) 0.9417(13) 0.2413(7) 0.064(3) Uani 1 1 d . . .
C9 C 0.3869(18) 0.8029(15) 0.1998(7) 0.080(4) Uani 1 1 d . . .
C10 C 0.5136(12) 0.6314(10) 0.2205(8) 0.053(3) Uani 1 1 d . . .
C11 C 0.5588(16) 0.5678(14) 0.3208(11) 0.091(4) Uani 1 1 d . . .
H11 H 0.5044 0.6308 0.3705 0.109 Uiso 1 1 calc R . .
C12 C 0.679(2) 0.418(2) 0.3474(11) 0.108(5) Uani 1 1 d . . .
H12 H 0.7112 0.3782 0.4158 0.130 Uiso 1 1 calc R . .
C13 C 0.7568(19) 0.3192(17) 0.2770(14) 0.107(5) Uani 1 1 d . . .
H13 H 0.8437 0.2148 0.2969 0.128 Uiso 1 1 calc R . .
C14 C 0.704(2) 0.3767(17) 0.1756(14) 0.115(5) Uani 1 1 d . . .
H14 H 0.7523 0.3078 0.1277 0.138 Uiso 1 1 calc R . .
C15 C 0.5806(19) 0.5373(17) 0.1436(9) 0.106(5) Uani 1 1 d . . .
H15 H 0.5456 0.5782 0.0756 0.127 Uiso 1 1 calc R . .
C16 C 0.2563(14) 0.9431(15) 0.3510(9) 0.072(3) Uani 1 1 d . . .
C17 C 0.2108(19) 1.0871(18) 0.4961(9) 0.103(5) Uani 1 1 d . . .
H17A H 0.3120 1.0086 0.5394 0.124 Uiso 1 1 calc R . .
H17B H 0.0986 1.0651 0.5137 0.124 Uiso 1 1 calc R . .
C18 C 0.193(2) 1.263(2) 0.5046(10) 0.125(6) Uani 1 1 d . . .
H18A H 0.0645 1.3300 0.5048 0.150 Uiso 1 1 calc R . .
H18B H 0.2527 1.2660 0.5678 0.150 Uiso 1 1 calc R . .
C19 C 0.278(2) 1.331(2) 0.4194(11) 0.133(6) Uani 1 1 d . . .
H19A H 0.4022 1.3217 0.4386 0.159 Uiso 1 1 calc R . .
H19B H 0.2080 1.4466 0.3967 0.159 Uiso 1 1 calc R . .
C20 C 0.279(2) 1.2293(16) 0.3367(9) 0.095(4) Uani 1 1 d . . .
H20A H 0.1835 1.2902 0.2849 0.114 Uiso 1 1 calc R . .
H20B H 0.3969 1.1999 0.3052 0.114 Uiso 1 1 calc R . .


_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 C7 1.346(13) . ?
O1 C9 1.429(11) . ?
O2 C16 1.227(13) . ?
N1 C7 1.302(11) . ?
N1 C8 1.365(12) . ?
N2 C16 1.331(14) . ?
N2 C17 1.465(14) . ?
N2 C20 1.477(14) . ?
C1 C6 1.348(15) . ?
C1 C2 1.395(16) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.362(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.414(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.433(17) . ?
C5 H5 0.9300 . ?
C6 C7 1.490(14) . ?
C8 C9 1.384(14) . ?
C8 C16 1.483(14) . ?
C9 C10 1.467(14) . ?
C10 C11 1.369(15) . ?
C10 C15 1.395(13) . ?
C11 C12 1.318(17) . ?
C11 H11 0.9300 . ?
C12 C13 1.365(18) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(18) . ?
C13 H13 0.9300 . ?
C14 C15 1.404(17) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C17 C18 1.507(17) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.456(18) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.507(16) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

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 O1 C9 107.0(9) . . ?
C7 N1 C8 105.4(9) . . ?
C16 N2 C17 119.6(11) . . ?
C16 N2 C20 127.9(11) . . ?
C17 N2 C20 112.3(10) . . ?
C6 C1 C2 121.7(14) . . ?
C6 C1 H1 119.2 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 117.3(14) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C4 C3 C2 123.3(15) . . ?
C4 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
C3 C4 C5 119.6(15) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 117.1(12) . . ?
C4 C5 H5 121.4 . . ?
C6 C5 H5 121.5 . . ?
C1 C6 C5 121.0(12) . . ?
C1 C6 C7 121.9(12) . . ?
C5 C6 C7 117.0(11) . . ?
N1 C7 O1 113.0(10) . . ?
N1 C7 C6 128.4(12) . . ?
O1 C7 C6 118.6(9) . . ?
N1 C8 C9 112.1(8) . . ?
N1 C8 C16 122.4(9) . . ?
C9 C8 C16 124.6(10) . . ?
C8 C9 O1 102.4(9) . . ?
C8 C9 C10 145.8(10) . . ?
O1 C9 C10 111.6(10) . . ?
C11 C10 C15 121.9(10) . . ?
C11 C10 C9 115.6(10) . . ?
C15 C10 C9 122.5(10) . . ?
C12 C11 C10 120.4(13) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 121.6(15) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C12 C13 C14 119.0(14) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C13 C14 C15 121.3(13) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C10 115.6(12) . . ?
C14 C15 H15 122.2 . . ?
C10 C15 H15 122.2 . . ?
O2 C16 N2 121.0(11) . . ?
O2 C16 C8 121.0(12) . . ?
N2 C16 C8 118.0(11) . . ?
N2 C17 C18 102.6(11) . . ?
N2 C17 H17A 111.3 . . ?
C18 C17 H17A 111.3 . . ?
N2 C17 H17B 111.2 . . ?
C18 C17 H17B 111.2 . . ?
H17A C17 H17B 109.2 . . ?
C19 C18 C17 109.6(12) . . ?
C19 C18 H18A 109.8 . . ?
C17 C18 H18A 109.8 . . ?
C19 C18 H18B 109.8 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C18 C19 C20 106.0(13) . . ?
C18 C19 H19A 110.5 . . ?
C20 C19 H19A 110.5 . . ?
C18 C19 H19B 110.5 . . ?
C20 C19 H19B 110.5 . . ?
H19A C19 H19B 108.7 . . ?
N2 C20 C19 104.7(11) . . ?
N2 C20 H20A 110.8 . . ?
C19 C20 H20A 110.8 . . ?
N2 C20 H20B 110.8 . . ?
C19 C20 H20B 110.8 . . ?
H20A C20 H20B 108.9 . . ?

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 C1 C2 C3 -2(2) . . . . ?
C1 C2 C3 C4 2(2) . . . . ?
C2 C3 C4 C5 -2(3) . . . . ?
C3 C4 C5 C6 0(2) . . . . ?
C2 C1 C6 C5 0(2) . . . . ?
C2 C1 C6 C7 177.9(12) . . . . ?
C4 C5 C6 C1 1(2) . . . . ?
C4 C5 C6 C7 -177.3(12) . . . . ?
C8 N1 C7 O1 0.7(12) . . . . ?
C8 N1 C7 C6 178.2(10) . . . . ?
C9 O1 C7 N1 1.7(11) . . . . ?
C9 O1 C7 C6 -176.1(9) . . . . ?
C1 C6 C7 N1 -179.7(12) . . . . ?
C5 C6 C7 N1 -1.9(17) . . . . ?
C1 C6 C7 O1 -2.3(16) . . . . ?
C5 C6 C7 O1 175.5(11) . . . . ?
C7 N1 C8 C9 -2.9(13) . . . . ?
C7 N1 C8 C16 -172.5(11) . . . . ?
N1 C8 C9 O1 3.8(13) . . . . ?
C16 C8 C9 O1 173.1(10) . . . . ?
N1 C8 C9 C10 177.3(15) . . . . ?
C16 C8 C9 C10 -13(3) . . . . ?
C7 O1 C9 C8 -3.2(12) . . . . ?
C7 O1 C9 C10 -179.3(8) . . . . ?
C8 C9 C10 C11 3(2) . . . . ?
O1 C9 C10 C11 175.9(9) . . . . ?
C8 C9 C10 C15 -178.6(17) . . . . ?
O1 C9 C10 C15 -5.5(15) . . . . ?
C15 C10 C11 C12 4.9(19) . . . . ?
C9 C10 C11 C12 -176.5(12) . . . . ?
C10 C11 C12 C13 -2(2) . . . . ?
C11 C12 C13 C14 -2(2) . . . . ?
C12 C13 C14 C15 3(2) . . . . ?
C13 C14 C15 C10 -1(2) . . . . ?
C11 C10 C15 C14 -3.2(18) . . . . ?
C9 C10 C15 C14 178.4(12) . . . . ?
C17 N2 C16 O2 -0.3(17) . . . . ?
C20 N2 C16 O2 174.9(11) . . . . ?
C17 N2 C16 C8 178.8(10) . . . . ?
C20 N2 C16 C8 -6.0(17) . . . . ?
N1 C8 C16 O2 134.3(12) . . . . ?
C9 C8 C16 O2 -33.9(18) . . . . ?
N1 C8 C16 N2 -44.8(16) . . . . ?
C9 C8 C16 N2 147.0(12) . . . . ?
C16 N2 C17 C18 -175.1(11) . . . . ?
C20 N2 C17 C18 9.0(14) . . . . ?
N2 C17 C18 C19 -19.6(17) . . . . ?
C17 C18 C19 C20 22.8(19) . . . . ?
C16 N2 C20 C19 -171.2(12) . . . . ?
C17 N2 C20 C19 4.2(14) . . . . ?
C18 C19 C20 N2 -16.3(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 976496'
