# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_nk_ard_anmn_0m
_database_code_depnum_ccdc_archive 'CCDC 1057348'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N3 O3'
_chemical_formula_weight         272.28

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                   6.9074(14)
_cell_length_b                   8.6886(19)
_cell_length_c                   10.502(2)
_cell_angle_alpha                85.367(11)
_cell_angle_beta                 89.740(10)
_cell_angle_gamma                79.832(10)
_cell_volume                     618.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             286
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_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 2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5816
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_av_sigmaI/netI    0.0722
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         21.88
_reflns_number_total             1479
_reflns_number_gt                822
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick,2008)'
_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)+(0.2000P)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         1479
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1574
_refine_ls_R_factor_gt           0.0998
_refine_ls_wR_factor_ref         0.3337
_refine_ls_wR_factor_gt          0.2841
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.184
_refine_ls_shift/su_mean         0.039

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
N2 N 0.8285(6) 0.0112(6) 0.2082(5) 0.0696(18) Uani 1 1 d . . .
H1 H 0.9335 0.0492 0.1917 0.083 Uiso 1 1 calc R . .
N1 N 0.5080(7) 0.0632(6) 0.2804(6) 0.083(2) Uani 1 1 d . . .
H2 H 0.4245 0.1319 0.3159 0.099 Uiso 1 1 calc R . .
O3 O 0.2662(6) -0.0505(5) 0.2085(4) 0.0764(16) Uani 1 1 d . . .
C1 C 0.7836(8) -0.1054(7) 0.1373(6) 0.0619(18) Uani 1 1 d . . .
C2 C 0.5947(8) -0.1358(7) 0.1384(6) 0.0642(19) Uani 1 1 d . . .
C3 C 0.5471(9) -0.2499(8) 0.0661(7) 0.083(2) Uani 1 1 d . . .
H3 H 0.4192 -0.2698 0.0680 0.100 Uiso 1 1 calc R . .
O1 O 0.7273(14) 0.7184(13) 0.5182(14) 0.203(6) Uani 1 1 d . . .
N3 N 0.7613(10) 0.5924(15) 0.5760(14) 0.135(4) Uani 1 1 d . . .
C11 C 0.7623(9) 0.4552(11) 0.4959(11) 0.083(3) Uani 1 1 d . . .
C10 C 0.7887(10) 0.3108(15) 0.5569(8) 0.094(3) Uani 1 1 d . . .
H9 H 0.8129 0.2970 0.6444 0.113 Uiso 1 1 calc R . .
C9 C 0.7799(11) 0.1885(11) 0.4913(13) 0.101(3) Uani 1 1 d . . .
H8 H 0.7985 0.0888 0.5337 0.121 Uiso 1 1 calc R . .
C8 C 0.7443(10) 0.2055(14) 0.3629(14) 0.102(3) Uani 1 1 d . . .
C7 C 0.7165(13) 0.0630(17) 0.2974(15) 0.240(9) Uani 1 1 d . . .
H7 H 0.7513 -0.0206 0.3660 0.289 Uiso 1 1 calc R . .
C4 C 0.6828(10) -0.3345(8) -0.0085(7) 0.089(2) Uani 1 1 d . . .
H4 H 0.6484 -0.4113 -0.0563 0.107 Uiso 1 1 calc R . .
C14 C 0.4419(9) -0.0389(7) 0.2120(7) 0.0677(19) Uani 1 1 d . . .
O2 O 0.7866(13) 0.5657(18) 0.6870(12) 0.239(8) Uani 1 1 d . . .
C12 C 0.7308(10) 0.4808(11) 0.3657(11) 0.094(3) Uani 1 1 d . . .
H10 H 0.7167 0.5811 0.3245 0.113 Uiso 1 1 calc R . .
C13 C 0.7210(11) 0.3512(18) 0.2985(9) 0.109(3) Uani 1 1 d . . .
H11 H 0.6988 0.3631 0.2107 0.131 Uiso 1 1 calc R . .
C6 C 0.9224(9) -0.1911(8) 0.0614(7) 0.084(2) Uani 1 1 d . . .
H6 H 1.0508 -0.1721 0.0597 0.100 Uiso 1 1 calc R . .
C5 C 0.8717(10) -0.3031(8) -0.0110(7) 0.084(2) Uani 1 1 d . . .
H5 H 0.9655 -0.3582 -0.0620 0.101 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
N2 0.035(3) 0.089(4) 0.093(4) -0.037(3) 0.016(3) -0.022(3)
N1 0.038(3) 0.104(4) 0.119(5) -0.059(4) 0.023(3) -0.026(3)
O3 0.032(2) 0.103(3) 0.100(4) -0.025(3) 0.008(2) -0.020(2)
C1 0.038(3) 0.077(4) 0.075(5) -0.022(4) 0.007(3) -0.015(3)
C2 0.034(3) 0.079(4) 0.084(5) -0.036(4) 0.004(3) -0.012(3)
C3 0.043(4) 0.103(5) 0.114(6) -0.040(5) 0.008(4) -0.026(4)
O1 0.118(7) 0.164(8) 0.351(17) -0.132(10) 0.090(9) -0.046(6)
N3 0.035(4) 0.172(9) 0.213(12) -0.086(10) 0.033(6) -0.026(5)
C11 0.035(4) 0.100(6) 0.127(8) -0.066(6) 0.025(4) -0.019(4)
C10 0.058(5) 0.137(8) 0.092(7) -0.023(7) 0.007(4) -0.026(5)
C9 0.062(5) 0.095(6) 0.148(10) -0.024(7) 0.024(6) -0.015(4)
C8 0.034(4) 0.133(8) 0.157(10) -0.085(8) 0.032(5) -0.033(5)
C7 0.058(5) 0.325(15) 0.41(2) -0.320(16) 0.101(9) -0.103(8)
C4 0.064(5) 0.096(5) 0.117(7) -0.051(5) 0.013(4) -0.023(4)
C14 0.035(4) 0.084(4) 0.089(5) -0.023(4) 0.007(3) -0.015(3)
O2 0.109(6) 0.43(2) 0.219(11) -0.224(14) 0.034(7) -0.069(8)
C12 0.054(4) 0.108(7) 0.122(8) -0.003(6) 0.019(5) -0.023(4)
C13 0.049(5) 0.200(11) 0.091(7) -0.055(8) 0.010(4) -0.037(6)
C6 0.041(3) 0.102(5) 0.116(6) -0.046(5) 0.014(4) -0.018(3)
C5 0.060(5) 0.087(5) 0.104(6) -0.034(4) 0.018(4) -0.001(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
N2 C7 1.272(10) . ?
N2 C1 1.383(7) . ?
N2 H1 0.8600 . ?
N1 C14 1.327(7) . ?
N1 C7 1.452(10) . ?
N1 H2 0.8600 . ?
O3 C14 1.236(7) . ?
C1 C2 1.376(8) . ?
C1 C6 1.395(8) . ?
C2 C3 1.381(8) . ?
C2 C14 1.485(8) . ?
C3 C4 1.369(9) . ?
C3 H3 0.9300 . ?
O1 N3 1.193(14) . ?
N3 O2 1.178(16) . ?
N3 C11 1.512(12) . ?
C11 C10 1.345(11) . ?
C11 C12 1.380(12) . ?
C10 C9 1.322(12) . ?
C10 H9 0.9300 . ?
C9 C8 1.363(13) . ?
C9 H8 0.9300 . ?
C8 C13 1.370(13) . ?
C8 C7 1.505(12) . ?
C7 H7 0.9800 . ?
C4 C5 1.379(9) . ?
C4 H4 0.9300 . ?
C12 C13 1.389(12) . ?
C12 H10 0.9300 . ?
C13 H11 0.9300 . ?
C6 C5 1.375(9) . ?
C6 H6 0.9300 . ?
C5 H5 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
C7 N2 C1 120.9(5) . . ?
C7 N2 H1 119.6 . . ?
C1 N2 H1 119.6 . . ?
C14 N1 C7 122.2(5) . . ?
C14 N1 H2 118.9 . . ?
C7 N1 H2 118.9 . . ?
C2 C1 N2 119.3(5) . . ?
C2 C1 C6 118.5(6) . . ?
N2 C1 C6 122.2(5) . . ?
C1 C2 C3 119.8(5) . . ?
C1 C2 C14 119.3(5) . . ?
C3 C2 C14 120.8(5) . . ?
C4 C3 C2 121.9(6) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
O2 N3 O1 127.0(14) . . ?
O2 N3 C11 118.0(15) . . ?
O1 N3 C11 114.9(14) . . ?
C10 C11 C12 122.3(8) . . ?
C10 C11 N3 117.6(12) . . ?
C12 C11 N3 120.1(11) . . ?
C9 C10 C11 119.5(9) . . ?
C9 C10 H9 120.3 . . ?
C11 C10 H9 120.3 . . ?
C10 C9 C8 121.5(9) . . ?
C10 C9 H8 119.3 . . ?
C8 C9 H8 119.2 . . ?
C9 C8 C13 120.0(9) . . ?
C9 C8 C7 118.2(14) . . ?
C13 C8 C7 121.6(15) . . ?
N2 C7 N1 116.4(9) . . ?
N2 C7 C8 122.1(9) . . ?
N1 C7 C8 109.6(7) . . ?
N2 C7 H7 101.6 . . ?
N1 C7 H7 101.6 . . ?
C8 C7 H7 101.5 . . ?
C3 C4 C5 118.4(6) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
O3 C14 N1 122.5(5) . . ?
O3 C14 C2 122.8(6) . . ?
N1 C14 C2 114.8(5) . . ?
C11 C12 C13 117.4(9) . . ?
C11 C12 H10 121.3 . . ?
C13 C12 H10 121.3 . . ?
C8 C13 C12 119.3(9) . . ?
C8 C13 H11 120.4 . . ?
C12 C13 H11 120.3 . . ?
C5 C6 C1 120.8(6) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C6 C5 C4 120.5(6) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        21.88
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.086
####################################################################### 
# 
# 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_nkpn
_database_code_depnum_ccdc_archive 'CCDC 1057349'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N2 O'
_chemical_formula_sum            'C12 H14 N2 O'
_chemical_formula_weight         202.25

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   'p b c a'
_symmetry_space_group_name_Hall  '-p 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   10.3180(16)
_cell_length_b                   12.0004(19)
_cell_length_c                   16.682(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2065.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       'cube shape'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4399
_diffrn_reflns_av_R_equivalents  0.1092
_diffrn_reflns_av_sigmaI/netI    0.0781
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         26.29
_reflns_number_total             1850
_reflns_number_gt                1550
_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    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX V1.80.03'

_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)+(0.1319P)²+0.9333P] 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       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1850
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.2052
_refine_ls_wR_factor_gt          0.1957
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_refine_ls_shift/su_max          0.010
_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 0.08324(15) 1.07506(11) 0.08230(9) 0.0418(5) Uani 1 1 d . . .
N1 N 0.14833(18) 0.91979(14) 0.01750(11) 0.0398(5) Uani 1 1 d . . .
H1 H 0.0762 0.9179 -0.0083 0.048 Uiso 1 1 calc R . .
N2 N 0.3075(2) 0.80234(16) 0.07024(11) 0.0452(6) Uani 1 1 d . . .
H2 H 0.3228 0.7328 0.0782 0.054 Uiso 1 1 calc R . .
C1 C 0.3972(3) 1.0384(2) 0.24415(15) 0.0544(7) Uani 1 1 d . . .
H1A H 0.4181 1.0917 0.2825 0.065 Uiso 1 1 calc R . .
C2 C 0.3027(3) 1.05972(19) 0.18842(15) 0.0468(6) Uani 1 1 d . . .
H2A H 0.2581 1.1270 0.1900 0.056 Uiso 1 1 calc R . .
C3 C 0.27288(19) 0.98138(17) 0.12927(13) 0.0358(5) Uani 1 1 d . . .
C4 C 0.1625(2) 0.99694(17) 0.07466(13) 0.0354(5) Uani 1 1 d . . .
C5 C 0.2482(2) 0.83848(17) -0.00367(13) 0.0376(6) Uani 1 1 d . . .
C6 C 0.1896(2) 0.7388(2) -0.04812(16) 0.0478(6) Uani 1 1 d . . .
H6A H 0.1691 0.6794 -0.0108 0.057 Uiso 1 1 calc R . .
H6B H 0.1107 0.7606 -0.0756 0.057 Uiso 1 1 calc R . .
C7 C 0.2885(4) 0.7011(3) -0.1067(2) 0.0852(11) Uani 1 1 d . . .
H7A H 0.2504 0.6949 -0.1597 0.102 Uiso 1 1 calc R . .
H7B H 0.3221 0.6287 -0.0914 0.102 Uiso 1 1 calc R . .
C8 C 0.3957(3) 0.7856(3) -0.1074(2) 0.0728(9) Uani 1 1 d . . .
H8A H 0.4179 0.8055 -0.1620 0.087 Uiso 1 1 calc R . .
H8B H 0.4723 0.7557 -0.0814 0.087 Uiso 1 1 calc R . .
C9 C 0.3471(3) 0.8864(2) -0.06260(15) 0.0513(7) Uani 1 1 d . . .
H9A H 0.3065 0.9391 -0.0988 0.062 Uiso 1 1 calc R . .
H9B H 0.4172 0.9233 -0.0344 0.062 Uiso 1 1 calc R . .
C10 C 0.3393(2) 0.87924(18) 0.12765(13) 0.0383(6) Uani 1 1 d . . .
C11 C 0.4327(2) 0.8578(2) 0.18634(14) 0.0490(6) Uani 1 1 d . . .
H11 H 0.4755 0.7896 0.1869 0.059 Uiso 1 1 calc R . .
C12 C 0.4615(3) 0.9364(2) 0.24286(15) 0.0553(7) Uani 1 1 d . . .
H12 H 0.5249 0.9216 0.2810 0.066 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
O1 0.0423(9) 0.0324(8) 0.0508(10) -0.0042(6) -0.0029(7) 0.0052(6)
N1 0.0384(10) 0.0361(10) 0.0450(11) -0.0080(8) -0.0095(8) 0.0050(7)
N2 0.0602(12) 0.0336(10) 0.0419(11) -0.0027(8) -0.0106(9) 0.0111(8)
C1 0.0631(15) 0.0589(15) 0.0411(13) -0.0074(11) -0.0086(11) -0.0129(12)
C2 0.0552(14) 0.0405(12) 0.0446(13) -0.0055(10) -0.0021(10) -0.0035(10)
C3 0.0376(11) 0.0355(11) 0.0342(11) 0.0020(8) 0.0005(8) -0.0026(8)
C4 0.0377(11) 0.0303(10) 0.0383(12) 0.0009(8) 0.0023(8) -0.0041(8)
C5 0.0397(11) 0.0326(10) 0.0405(12) -0.0031(8) -0.0043(9) 0.0021(8)
C6 0.0498(12) 0.0415(12) 0.0522(14) -0.0132(11) -0.0057(11) -0.0001(10)
C7 0.093(2) 0.072(2) 0.091(2) -0.0348(19) 0.030(2) -0.0148(18)
C8 0.0666(17) 0.077(2) 0.0747(19) -0.0124(16) 0.0144(16) 0.0015(15)
C9 0.0571(15) 0.0503(14) 0.0466(14) -0.0004(11) 0.0063(11) -0.0022(11)
C10 0.0402(11) 0.0396(11) 0.0351(11) 0.0023(9) 0.0017(8) 0.0012(8)
C11 0.0503(13) 0.0562(14) 0.0404(13) 0.0042(11) -0.0037(10) 0.0101(11)
C12 0.0532(14) 0.0723(18) 0.0404(13) 0.0042(12) -0.0098(11) -0.0009(12)

_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 C4 1.251(3) . ?
N1 C4 1.337(3) . ?
N1 C5 1.462(3) . ?
N1 H1 0.8600 . ?
N2 C10 1.370(3) . ?
N2 C5 1.443(3) . ?
N2 H2 0.8600 . ?
C1 C2 1.371(4) . ?
C1 C12 1.393(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.397(3) . ?
C2 H2A 0.9300 . ?
C3 C10 1.405(3) . ?
C3 C4 1.470(3) . ?
C5 C9 1.529(3) . ?
C5 C6 1.532(3) . ?
C6 C7 1.484(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.501(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.507(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.397(3) . ?
C11 C12 1.366(4) . ?
C11 H11 0.9300 . ?
C12 H12 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
C4 N1 C5 123.87(18) . . ?
C4 N1 H1 118.1 . . ?
C5 N1 H1 118.1 . . ?
C10 N2 C5 119.77(18) . . ?
C10 N2 H2 120.1 . . ?
C5 N2 H2 120.1 . . ?
C2 C1 C12 119.5(2) . . ?
C2 C1 H1A 120.3 . . ?
C12 C1 H1A 120.3 . . ?
C1 C2 C3 120.7(2) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C2 C3 C10 119.6(2) . . ?
C2 C3 C4 121.5(2) . . ?
C10 C3 C4 118.48(19) . . ?
O1 C4 N1 121.34(19) . . ?
O1 C4 C3 122.59(19) . . ?
N1 C4 C3 116.02(18) . . ?
N2 C5 N1 107.04(18) . . ?
N2 C5 C9 112.29(19) . . ?
N1 C5 C9 111.98(18) . . ?
N2 C5 C6 110.26(18) . . ?
N1 C5 C6 111.10(17) . . ?
C9 C5 C6 104.23(19) . . ?
C7 C6 C5 106.6(2) . . ?
C7 C6 H6A 110.4 . . ?
C5 C6 H6A 110.4 . . ?
C7 C6 H6B 110.4 . . ?
C5 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?
C6 C7 C8 107.8(2) . . ?
C6 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
C6 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.5 . . ?
C7 C8 C9 107.0(2) . . ?
C7 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
C7 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
C8 C9 C5 103.8(2) . . ?
C8 C9 H9A 111.0 . . ?
C5 C9 H9A 111.0 . . ?
C8 C9 H9B 111.0 . . ?
C5 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
N2 C10 C11 122.1(2) . . ?
N2 C10 C3 118.97(19) . . ?
C11 C10 C3 118.9(2) . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C1 120.9(2) . . ?
C11 C12 H12 119.5 . . ?
C1 C12 H12 119.5 . . ?

_diffrn_measured_fraction_theta_max 0.881
_diffrn_reflns_theta_full        26.29
_diffrn_measured_fraction_theta_full 0.881
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_ard_nkmet_01
_database_code_depnum_ccdc_archive 'CCDC 1416677'
_audit_update_record             
;
2015-08-03 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N2 O'
_chemical_formula_sum            'C15 H14 N2 O'
_chemical_formula_weight         238.28

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   P12(1)/n1
_symmetry_space_group_name_Hall  '-P 2yn'

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                   8.5600(3)
_cell_length_b                   8.8072(3)
_cell_length_c                   16.2462(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.334(2)
_cell_angle_gamma                90.00
_cell_volume                     1222.72(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       granular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_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      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  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2790
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         26.39
_reflns_number_total             1732
_reflns_number_gt                1339
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1477P)²+0.1958P] 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         1732
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1779
_refine_ls_wR_factor_gt          0.1611
_refine_ls_goodness_of_fit_ref   0.876
_refine_ls_restrained_S_all      0.876
_refine_ls_shift/su_max          0.116
_refine_ls_shift/su_mean         0.021

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 0.09004(19) 0.3691(2) 1.08021(8) 0.0551(6) Uani 1 1 d . . .
N1 N 0.05588(19) 0.3416(2) 0.94234(9) 0.0410(6) Uani 1 1 d . . .
H1 H -0.0143 0.4116 0.9394 0.049 Uiso 1 1 calc R . .
N2 N 0.1159(2) 0.1134(3) 0.87731(10) 0.0480(7) Uani 1 1 d . . .
H2 H 0.0749 0.0531 0.8404 0.058 Uiso 1 1 calc R . .
C1 C 0.3405(3) -0.0421(4) 1.09534(15) 0.0616(9) Uani 1 1 d . . .
H1A H 0.3935 -0.0747 1.1437 0.074 Uiso 1 1 calc R . .
C2 C 0.2751(2) 0.0984(3) 1.09094(13) 0.0474(7) Uani 1 1 d . . .
H2A H 0.2819 0.1607 1.1372 0.057 Uiso 1 1 calc R . .
C3 C 0.1986(2) 0.1508(3) 1.01921(12) 0.0377(7) Uani 1 1 d . . .
C4 C 0.1136(2) 0.2951(3) 1.01677(11) 0.0392(7) Uani 1 1 d . . .
C5 C 0.1095(2) 0.2761(4) 0.86632(11) 0.0380(7) Uani 1 1 d . . .
C6 C 0.2713(2) 0.3402(3) 0.84753(11) 0.0390(7) Uani 1 1 d . . .
C7 C 0.3503(3) 0.2764(3) 0.78332(13) 0.0555(8) Uani 1 1 d . . .
H7 H 0.3055 0.1961 0.7532 0.067 Uiso 1 1 calc R . .
C8 C 0.4947(3) 0.3315(4) 0.76411(18) 0.0733(11) Uani 1 1 d . . .
H8 H 0.5457 0.2892 0.7206 0.088 Uiso 1 1 calc R . .
C9 C 0.5630(3) 0.4477(5) 0.8086(2) 0.0782(11) Uani 1 1 d . . .
H9 H 0.6613 0.4829 0.7962 0.094 Uiso 1 1 calc R . .
C10 C 0.1898(2) 0.0577(3) 0.94876(12) 0.0396(7) Uani 1 1 d . . .
C11 C 0.4863(3) 0.5123(4) 0.87156(17) 0.0693(9) Uani 1 1 d . . .
H11 H 0.5322 0.5923 0.9014 0.083 Uiso 1 1 calc R . .
C12 C 0.3409(3) 0.4590(3) 0.89082(13) 0.0518(7) Uani 1 1 d . . .
H12 H 0.2896 0.5039 0.9335 0.062 Uiso 1 1 calc R . .
C13 C -0.0098(3) 0.3171(3) 0.79620(13) 0.0553(8) Uani 1 1 d . . .
H13A H 0.0230 0.2752 0.7454 0.083 Uiso 1 1 calc R . .
H13B H -0.0172 0.4255 0.7914 0.083 Uiso 1 1 calc R . .
H13C H -0.1102 0.2762 0.8077 0.083 Uiso 1 1 calc R . .
C14 C 0.2536(3) -0.0882(4) 0.95431(15) 0.0573(8) Uani 1 1 d . . .
H14 H 0.2460 -0.1525 0.9088 0.069 Uiso 1 1 calc R . .
C15 C 0.3274(3) -0.1367(4) 1.02671(18) 0.0681(9) Uani 1 1 d . . .
H15 H 0.3692 -0.2341 1.0300 0.082 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
O1 0.0817(11) 0.0471(17) 0.0367(8) -0.0024(7) 0.0065(7) 0.0192(9)
N1 0.0443(9) 0.0406(18) 0.0382(9) -0.0018(8) 0.0030(7) 0.0134(8)
N2 0.0621(11) 0.035(2) 0.0453(10) -0.0080(9) -0.0095(8) 0.0007(10)
C1 0.0704(16) 0.053(3) 0.0597(15) 0.0163(13) -0.0052(11) 0.0127(15)
C2 0.0503(12) 0.047(2) 0.0447(11) 0.0062(11) 0.0004(8) 0.0040(12)
C3 0.0389(10) 0.034(2) 0.0410(10) 0.0022(9) 0.0050(8) -0.0010(10)
C4 0.0424(10) 0.038(2) 0.0373(10) 0.0003(9) 0.0040(8) 0.0016(10)
C5 0.0483(11) 0.031(2) 0.0338(10) -0.0045(9) -0.0021(8) 0.0087(10)
C6 0.0500(11) 0.035(2) 0.0315(9) 0.0054(9) -0.0006(8) 0.0107(10)
C7 0.0670(14) 0.055(2) 0.0452(12) 0.0084(11) 0.0114(10) 0.0220(13)
C8 0.0719(17) 0.082(3) 0.0688(17) 0.0295(17) 0.0294(14) 0.0330(18)
C9 0.0533(14) 0.086(3) 0.097(2) 0.051(2) 0.0183(15) 0.0131(16)
C10 0.0417(10) 0.029(2) 0.0480(11) 0.0021(10) 0.0027(8) -0.0025(10)
C11 0.0643(15) 0.066(3) 0.0765(17) 0.0202(15) -0.0042(13) -0.0125(14)
C12 0.0575(13) 0.052(2) 0.0458(12) 0.0041(11) 0.0031(9) -0.0025(12)
C13 0.0594(13) 0.061(2) 0.0439(12) -0.0034(11) -0.0126(9) 0.0097(12)
C14 0.0708(15) 0.039(2) 0.0623(15) -0.0001(12) 0.0034(11) 0.0062(15)
C15 0.0801(18) 0.044(3) 0.0801(18) 0.0107(14) 0.0053(14) 0.0185(14)

_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 C4 1.246(2) . ?
N1 C4 1.343(3) . ?
N1 C5 1.461(2) . ?
N1 H1 0.8600 . ?
N2 C10 1.379(3) . ?
N2 C5 1.444(3) . ?
N2 H2 0.8600 . ?
C1 C2 1.358(4) . ?
C1 C15 1.391(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.382(3) . ?
C2 H2A 0.9300 . ?
C3 C10 1.406(3) . ?
C3 C4 1.464(3) . ?
C5 C13 1.528(3) . ?
C5 C6 1.543(3) . ?
C6 C12 1.377(3) . ?
C6 C7 1.394(3) . ?
C7 C8 1.380(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.364(5) . ?
C8 H8 0.9300 . ?
C9 C11 1.372(4) . ?
C9 H9 0.9300 . ?
C10 C14 1.398(4) . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.371(4) . ?
C14 H14 0.9300 . ?
C15 H15 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
C4 N1 C5 121.55(18) . . ?
C4 N1 H1 119.2 . . ?
C5 N1 H1 119.2 . . ?
C10 N2 C5 117.97(19) . . ?
C10 N2 H2 121.0 . . ?
C5 N2 H2 121.0 . . ?
C2 C1 C15 119.3(2) . . ?
C2 C1 H1A 120.3 . . ?
C15 C1 H1A 120.3 . . ?
C1 C2 C3 121.5(2) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
C2 C3 C10 119.5(2) . . ?
C2 C3 C4 121.5(2) . . ?
C10 C3 C4 118.73(19) . . ?
O1 C4 N1 121.1(2) . . ?
O1 C4 C3 122.39(18) . . ?
N1 C4 C3 116.45(18) . . ?
N2 C5 N1 107.40(18) . . ?
N2 C5 C13 110.21(19) . . ?
N1 C5 C13 107.91(19) . . ?
N2 C5 C6 111.08(18) . . ?
N1 C5 C6 110.63(19) . . ?
C13 C5 C6 109.54(18) . . ?
C12 C6 C7 118.3(2) . . ?
C12 C6 C5 122.96(19) . . ?
C7 C6 C5 118.7(2) . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C11 119.8(3) . . ?
C8 C9 H9 120.1 . . ?
C11 C9 H9 120.1 . . ?
N2 C10 C14 122.7(2) . . ?
N2 C10 C3 118.6(2) . . ?
C14 C10 C3 118.8(2) . . ?
C9 C11 C12 120.3(3) . . ?
C9 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C6 C12 C11 120.7(2) . . ?
C6 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C10 120.1(3) . . ?
C15 C14 H14 120.0 . . ?
C10 C14 H14 120.0 . . ?
C14 C15 C1 120.8(3) . . ?
C14 C15 H15 119.6 . . ?
C1 C15 H15 119.6 . . ?

_diffrn_measured_fraction_theta_max 0.691
_diffrn_reflns_theta_full        26.39
_diffrn_measured_fraction_theta_full 0.691
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.058
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.044
;
