# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xu1
_database_code_depnum_ccdc_archive 'CCDC 1012731'
_audit_update_record             
;
2014-07-08 deposited with the CCDC.
2015-03-19 downloaded from the CCDC.
;

_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           ?
_symmetry_space_group_name_H-M   ?

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                   15.005(3)
_cell_length_b                   12.061(2)
_cell_length_c                   18.219(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3297.4(11)
_cell_formula_units_Z            16
_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    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    0.084
_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            23169
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2874
_reflns_number_gt                1569
_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)+(0.1159P)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     SHELXL
_refine_ls_extinction_coef       0.0046(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2874
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1890
_refine_ls_wR_factor_gt          0.1529
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_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 1.01109(14) 0.22851(17) 0.46320(13) 0.0687(7) Uani 1 1 d . . .
H1A H 1.0233 0.1851 0.4993 0.082 Uiso 1 1 calc R . .
O1 O 1.08953(15) 0.13651(16) 0.37398(12) 0.0860(7) Uani 1 1 d . . .
C1 C 1.00399(17) 0.3043(2) 0.34986(16) 0.0629(7) Uani 1 1 d . . .
C2 C 0.95421(18) 0.3710(2) 0.39592(17) 0.0651(7) Uani 1 1 d . . .
C8 C 0.95792(17) 0.3249(2) 0.46982(16) 0.0661(7) Uani 1 1 d . . .
C7 C 1.04052(19) 0.2122(2) 0.39390(17) 0.0662(7) Uani 1 1 d . . .
C5 C 0.96977(19) 0.4184(2) 0.24858(19) 0.0797(9) Uani 1 1 d . . .
H5A H 0.9746 0.4356 0.1990 0.096 Uiso 1 1 calc R . .
C3 C 0.9121(2) 0.4638(2) 0.36761(19) 0.0811(9) Uani 1 1 d . . .
H3A H 0.8790 0.5104 0.3979 0.097 Uiso 1 1 calc R . .
C6 C 1.01224(18) 0.3261(2) 0.27612(17) 0.0746(8) Uani 1 1 d . . .
H6A H 1.0455 0.2800 0.2457 0.090 Uiso 1 1 calc R . .
C4 C 0.9201(2) 0.4856(2) 0.2942(2) 0.0841(9) Uani 1 1 d . . .
H4A H 0.8913 0.5472 0.2746 0.101 Uiso 1 1 calc R . .
O2 O 0.06645(14) 0.42755(15) 0.07374(12) 0.0822(7) Uani 1 1 d . . .
N2 N 0.15641(14) 0.50604(17) -0.01393(14) 0.0707(7) Uani 1 1 d . . .
H2A H 0.1403 0.4652 -0.0503 0.085 Uiso 1 1 calc R . .
C11 C 0.16810(17) 0.5797(2) 0.10016(17) 0.0640(7) Uani 1 1 d . . .
C18 C 0.22019(18) 0.5909(2) -0.01941(18) 0.0678(8) Uani 1 1 d . . .
C17 C 0.12282(18) 0.4955(2) 0.05514(17) 0.0673(7) Uani 1 1 d . . .
C16 C 0.22513(18) 0.6383(2) 0.05428(18) 0.0689(8) Uani 1 1 d . . .
C15 C 0.2757(2) 0.7241(2) 0.0827(2) 0.0820(9) Uani 1 1 d . . .
H15A H 0.3139 0.7647 0.0528 0.098 Uiso 1 1 calc R . .
C14 C 0.2680(2) 0.7477(3) 0.1560(2) 0.0870(10) Uani 1 1 d . . .
H14A H 0.3015 0.8053 0.1757 0.104 Uiso 1 1 calc R . .
C12 C 0.16113(19) 0.6032(2) 0.17325(18) 0.0779(9) Uani 1 1 d . . .
H12A H 0.1231 0.5627 0.2034 0.093 Uiso 1 1 calc R . .
C13 C 0.2120(2) 0.6882(2) 0.2011(2) 0.0866(10) Uani 1 1 d . . .
H13A H 0.2085 0.7057 0.2507 0.104 Uiso 1 1 calc R . .
C9 C 0.9211(2) 0.3614(2) 0.53085(18) 0.0805(9) Uani 1 1 d . . .
H9A H 0.8883 0.4266 0.5278 0.097 Uiso 1 1 calc R . .
C10 C 0.9271(2) 0.3076(3) 0.60456(19) 0.0998(11) Uani 1 1 d . . .
H10A H 0.8937 0.3501 0.6395 0.150 Uiso 1 1 calc R . .
H10B H 0.9884 0.3043 0.6196 0.150 Uiso 1 1 calc R . .
H10C H 0.9033 0.2339 0.6019 0.150 Uiso 1 1 calc R . .
C19 C 0.2656(2) 0.6167(2) -0.07870(19) 0.0827(9) Uani 1 1 d . . .
H19A H 0.3048 0.6762 -0.0748 0.099 Uiso 1 1 calc R . .
C20 C 0.2609(2) 0.5611(3) -0.1514(2) 0.0994(11) Uani 1 1 d . . .
H20A H 0.3012 0.5968 -0.1849 0.149 Uiso 1 1 calc R . .
H20B H 0.2013 0.5659 -0.1702 0.149 Uiso 1 1 calc R . .
H20C H 0.2773 0.4846 -0.1462 0.149 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
N1 C7 1.352(4) . ?
N1 C8 1.415(3) . ?
O1 C7 1.227(3) . ?
C1 C6 1.375(4) . ?
C1 C2 1.382(4) . ?
C1 C7 1.476(4) . ?
C2 C3 1.386(4) . ?
C2 C8 1.458(4) . ?
C8 C9 1.317(4) . ?
C5 C6 1.377(4) . ?
C5 C4 1.380(4) . ?
C3 C4 1.368(4) . ?
O2 C17 1.226(3) . ?
N2 C17 1.362(4) . ?
N2 C18 1.405(3) . ?
C11 C12 1.365(4) . ?
C11 C16 1.389(4) . ?
C11 C17 1.472(4) . ?
C18 C19 1.314(4) . ?
C18 C16 1.461(4) . ?
C16 C15 1.383(4) . ?
C15 C14 1.370(5) . ?
C14 C13 1.378(5) . ?
C12 C13 1.376(4) . ?
C9 C10 1.494(4) . ?
C19 C20 1.487(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
C7 N1 C8 112.5(2) . . ?
C6 C1 C2 122.1(3) . . ?
C6 C1 C7 130.0(3) . . ?
C2 C1 C7 108.0(3) . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 C8 108.6(2) . . ?
C3 C2 C8 132.0(3) . . ?
C9 C8 N1 125.6(3) . . ?
C9 C8 C2 129.5(3) . . ?
N1 C8 C2 104.8(2) . . ?
O1 C7 N1 125.5(3) . . ?
O1 C7 C1 128.4(3) . . ?
N1 C7 C1 106.1(2) . . ?
C6 C5 C4 120.3(3) . . ?
C4 C3 C2 118.6(3) . . ?
C1 C6 C5 118.0(3) . . ?
C3 C4 C5 121.6(3) . . ?
C17 N2 C18 112.7(2) . . ?
C12 C11 C16 121.9(3) . . ?
C12 C11 C17 130.6(3) . . ?
C16 C11 C17 107.4(3) . . ?
C19 C18 N2 125.7(3) . . ?
C19 C18 C16 129.5(3) . . ?
N2 C18 C16 104.7(2) . . ?
O2 C17 N2 125.0(3) . . ?
O2 C17 C11 128.8(3) . . ?
N2 C17 C11 106.2(2) . . ?
C15 C16 C11 119.6(3) . . ?
C15 C16 C18 131.6(3) . . ?
C11 C16 C18 108.9(2) . . ?
C14 C15 C16 118.3(3) . . ?
C15 C14 C13 121.7(3) . . ?
C11 C12 C13 118.1(3) . . ?
C12 C13 C14 120.4(3) . . ?
C8 C9 C10 126.0(3) . . ?
C18 C19 C20 127.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.048
