# 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_ck135
_database_code_depnum_ccdc_archive 'CCDC 1468852'
_audit_update_record             
;
2016-04-30 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H16 N2 O'
_chemical_formula_sum            'C16 H16 N2 O'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         252.31

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'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

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

_cell_length_a                   8.5162(8)
_cell_length_b                   8.7051(8)
_cell_length_c                   9.9918(9)
_cell_angle_alpha                88.828(7)
_cell_angle_beta                 73.814(8)
_cell_angle_gamma                64.126(9)
_cell_volume                     635.66(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1951
_cell_measurement_theta_min      2.7810
_cell_measurement_theta_max      29.1503
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.99544
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) 
(compiled Jan 23 2012,18:06:46) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5683
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         29.21
_reflns_number_total             2928
_reflns_number_gt                2359
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0707P)²+0.3892P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2928
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
O O 0.23100(19) 0.66290(17) 0.11699(13) 0.0286(3) Uani 1 1 d . . .
N1 N 0.51725(19) 0.33950(19) 0.27363(15) 0.0206(3) Uani 1 1 d . . .
N2 N 0.2684(2) 0.57000(18) 0.21851(15) 0.0197(3) Uani 1 1 d . . .
C1 C 0.4169(2) 0.3657(2) 0.41326(17) 0.0189(4) Uani 1 1 d . . .
C2 C 0.4849(3) 0.2660(2) 0.51454(19) 0.0256(4) Uani 1 1 d . . .
H2A H 0.6048 0.1733 0.4881 0.031 Uiso 1 1 calc R . .
C3 C 0.3769(3) 0.3029(3) 0.65349(19) 0.0286(4) Uani 1 1 d . . .
H3A H 0.4239 0.2350 0.7217 0.034 Uiso 1 1 calc R . .
C4 C 0.2015(3) 0.4373(3) 0.69435(19) 0.0270(4) Uani 1 1 d . . .
H4A H 0.1280 0.4597 0.7895 0.032 Uiso 1 1 calc R . .
C5 C 0.1340(2) 0.5385(2) 0.59584(18) 0.0215(4) Uani 1 1 d . . .
H5A H 0.0144 0.6315 0.6243 0.026 Uiso 1 1 calc R . .
C6 C 0.2395(2) 0.5060(2) 0.45462(17) 0.0184(4) Uani 1 1 d . . .
C7 C 0.1778(2) 0.6202(2) 0.35232(18) 0.0195(4) Uani 1 1 d . . .
C8 C 0.4181(2) 0.3905(2) 0.17196(17) 0.0191(4) Uani 1 1 d . . .
H8A H 0.5045 0.3918 0.0812 0.023 Uiso 1 1 calc R . .
C9 C 0.3350(2) 0.2744(2) 0.14411(17) 0.0182(4) Uani 1 1 d . . .
C10 C 0.2352(2) 0.3151(2) 0.04760(18) 0.0222(4) Uani 1 1 d . . .
H10A H 0.2204 0.4136 -0.0002 0.027 Uiso 1 1 calc R . .
C11 C 0.1576(3) 0.2121(2) 0.02127(19) 0.0256(4) Uani 1 1 d . . .
H11A H 0.0878 0.2418 -0.0429 0.031 Uiso 1 1 calc R . .
C12 C 0.1817(2) 0.0667(2) 0.08837(19) 0.0245(4) Uani 1 1 d . . .
H12A H 0.1283 -0.0034 0.0706 0.029 Uiso 1 1 calc R . .
C13 C 0.2837(2) 0.0232(2) 0.1813(2) 0.0255(4) Uani 1 1 d . . .
H13A H 0.3022 -0.0781 0.2260 0.031 Uiso 1 1 calc R . .
C14 C 0.3594(2) 0.1272(2) 0.20984(19) 0.0218(4) Uani 1 1 d . . .
H14A H 0.4282 0.0972 0.2747 0.026 Uiso 1 1 calc R . .
C15 C 0.7090(2) 0.2157(3) 0.2235(2) 0.0264(4) Uani 1 1 d . . .
H15A H 0.7604 0.1914 0.3023 0.040 Uiso 1 1 calc R . .
H15B H 0.7757 0.2630 0.1528 0.040 Uiso 1 1 calc R . .
H15C H 0.7202 0.1091 0.1817 0.040 Uiso 1 1 calc R . .
C16 C 0.0191(3) 0.7951(2) 0.3927(2) 0.0263(4) Uani 1 1 d . . .
H16A H 0.0008 0.8497 0.3079 0.040 Uiso 1 1 calc R . .
H16B H 0.0439 0.8653 0.4516 0.040 Uiso 1 1 calc R . .
H16C H -0.0913 0.7851 0.4450 0.040 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
O 0.0392(8) 0.0221(7) 0.0246(7) 0.0103(5) -0.0109(6) -0.0134(6)
N1 0.0163(7) 0.0232(8) 0.0202(7) 0.0001(6) -0.0044(6) -0.0075(6)
N2 0.0241(7) 0.0167(7) 0.0211(7) 0.0055(6) -0.0077(6) -0.0110(6)
C1 0.0190(8) 0.0203(8) 0.0197(8) -0.0001(6) -0.0060(6) -0.0107(7)
C2 0.0218(9) 0.0251(9) 0.0255(9) 0.0007(7) -0.0096(7) -0.0052(7)
C3 0.0315(10) 0.0297(10) 0.0228(9) 0.0054(8) -0.0132(8) -0.0094(8)
C4 0.0282(10) 0.0290(10) 0.0200(8) 0.0007(7) -0.0054(7) -0.0106(8)
C5 0.0194(8) 0.0203(9) 0.0224(8) -0.0007(7) -0.0050(7) -0.0074(7)
C6 0.0198(8) 0.0170(8) 0.0212(8) 0.0019(6) -0.0073(7) -0.0101(7)
C7 0.0202(8) 0.0164(8) 0.0235(8) 0.0010(7) -0.0060(7) -0.0098(7)
C8 0.0195(8) 0.0201(8) 0.0167(7) 0.0024(6) -0.0037(6) -0.0093(7)
C9 0.0158(8) 0.0180(8) 0.0165(7) -0.0019(6) -0.0009(6) -0.0059(7)
C10 0.0261(9) 0.0207(9) 0.0185(8) 0.0022(7) -0.0071(7) -0.0093(7)
C11 0.0272(9) 0.0287(10) 0.0220(8) -0.0001(7) -0.0103(7) -0.0116(8)
C12 0.0201(8) 0.0218(9) 0.0294(9) -0.0046(7) -0.0051(7) -0.0087(7)
C13 0.0231(9) 0.0181(9) 0.0346(10) 0.0039(7) -0.0084(8) -0.0088(7)
C14 0.0189(8) 0.0202(9) 0.0259(9) 0.0041(7) -0.0087(7) -0.0072(7)
C15 0.0165(8) 0.0308(10) 0.0271(9) -0.0037(8) -0.0042(7) -0.0075(8)
C16 0.0283(9) 0.0166(9) 0.0303(10) 0.0031(7) -0.0093(8) -0.0064(7)

_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
O N2 1.3061(19) . ?
N1 C1 1.381(2) . ?
N1 C8 1.441(2) . ?
N1 C15 1.452(2) . ?
N2 C7 1.315(2) . ?
N2 C8 1.498(2) . ?
C1 C2 1.402(3) . ?
C1 C6 1.416(2) . ?
C2 C3 1.388(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.402(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.453(2) . ?
C7 C16 1.494(2) . ?
C8 C9 1.531(2) . ?
C8 H8A 1.0000 . ?
C9 C14 1.388(2) . ?
C9 C10 1.399(2) . ?
C10 C11 1.390(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.382(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.381(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.393(2) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C1 N1 C8 117.62(14) . . ?
C1 N1 C15 121.70(15) . . ?
C8 N1 C15 117.39(14) . . ?
O N2 C7 124.72(15) . . ?
O N2 C8 114.95(13) . . ?
C7 N2 C8 120.19(14) . . ?
N1 C1 C2 123.36(16) . . ?
N1 C1 C6 117.09(16) . . ?
C2 C1 C6 119.48(16) . . ?
C3 C2 C1 119.90(17) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C4 C3 C2 121.02(18) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C5 C4 C3 119.63(17) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C4 C5 C6 121.02(16) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C1 C6 C5 118.91(16) . . ?
C1 C6 C7 119.16(15) . . ?
C5 C6 C7 121.74(16) . . ?
N2 C7 C6 118.80(15) . . ?
N2 C7 C16 118.30(16) . . ?
C6 C7 C16 122.87(15) . . ?
N1 C8 N2 108.88(13) . . ?
N1 C8 C9 115.56(14) . . ?
N2 C8 C9 108.77(13) . . ?
N1 C8 H8A 107.8 . . ?
N2 C8 H8A 107.8 . . ?
C9 C8 H8A 107.8 . . ?
C14 C9 C10 118.90(16) . . ?
C14 C9 C8 121.70(15) . . ?
C10 C9 C8 119.39(15) . . ?
C9 C10 C11 120.39(17) . . ?
C9 C10 H10A 119.8 . . ?
C11 C10 H10A 119.8 . . ?
C12 C11 C10 120.08(17) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C11 C12 C13 119.96(17) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C12 C13 C14 120.24(17) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C9 C14 C13 120.40(16) . . ?
C9 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.847
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_ck148
_database_code_depnum_ccdc_archive 'CCDC 1468853'
_audit_update_record             
;
2016-04-30 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H12 N2 O'
_chemical_formula_sum            'C15 H12 N2 O'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            'Light yellow'

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         236.27

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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_int_tables_number      61
_chemical_absolute_configuration ?

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                   9.1061(4)
_cell_length_b                   14.8919(8)
_cell_length_c                   17.2862(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2344.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3541
_cell_measurement_theta_min      4.2370
_cell_measurement_theta_max      28.8770
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96403
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11838
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         29.33
_reflns_number_total             2842
_reflns_number_gt                2373
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0542P)²+1.2018P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2842
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
O O 0.08031(13) 0.13099(9) 0.57094(6) 0.0423(3) Uani 1 1 d . . .
N1 N 0.10177(12) 0.09241(8) 0.69738(7) 0.0256(3) Uani 1 1 d . . .
N2 N 0.23258(12) 0.18803(8) 0.78281(6) 0.0212(3) Uani 1 1 d . . .
C1 C 0.13835(15) 0.14480(10) 0.63422(8) 0.0278(3) Uani 1 1 d . . .
C2 C 0.24896(15) 0.21501(10) 0.64584(8) 0.0258(3) Uani 1 1 d . . .
C3 C 0.30977(18) 0.26226(11) 0.58333(9) 0.0346(4) Uani 1 1 d . . .
H3A H 0.2833 0.2463 0.5320 0.041 Uiso 1 1 calc R . .
C4 C 0.40727(19) 0.33146(12) 0.59550(10) 0.0409(4) Uani 1 1 d . . .
H4A H 0.4497 0.3622 0.5529 0.049 Uiso 1 1 calc R . .
C5 C 0.44314(18) 0.35599(11) 0.67123(11) 0.0391(4) Uani 1 1 d . . .
H5A H 0.5076 0.4052 0.6797 0.047 Uiso 1 1 calc R . .
C6 C 0.38680(16) 0.31022(10) 0.73389(9) 0.0310(3) Uani 1 1 d . . .
H6A H 0.4133 0.3272 0.7850 0.037 Uiso 1 1 calc R . .
C7 C 0.28989(14) 0.23836(9) 0.72151(8) 0.0235(3) Uani 1 1 d . . .
C8 C 0.15062(14) 0.11381(9) 0.76631(8) 0.0210(3) Uani 1 1 d . . .
C9 C 0.11630(14) 0.04910(9) 0.82935(8) 0.0226(3) Uani 1 1 d . . .
C10 C 0.22458(15) 0.01842(10) 0.88036(8) 0.0264(3) Uani 1 1 d . . .
H10A H 0.3212 0.0423 0.8778 0.032 Uiso 1 1 calc R . .
C11 C 0.19048(18) -0.04697(10) 0.93467(9) 0.0335(4) Uani 1 1 d . . .
H11A H 0.2640 -0.0682 0.9691 0.040 Uiso 1 1 calc R . .
C12 C 0.0488(2) -0.08143(11) 0.93879(10) 0.0392(4) Uani 1 1 d . . .
H12A H 0.0256 -0.1258 0.9763 0.047 Uiso 1 1 calc R . .
C13 C -0.05840(18) -0.05133(11) 0.88838(11) 0.0376(4) Uani 1 1 d . . .
H13A H -0.1552 -0.0748 0.8916 0.045 Uiso 1 1 calc R . .
C14 C -0.02488(15) 0.01299(10) 0.83324(9) 0.0294(3) Uani 1 1 d . . .
H14A H -0.0982 0.0326 0.7980 0.035 Uiso 1 1 calc R . .
C15 C 0.25281(16) 0.22110(10) 0.86249(8) 0.0264(3) Uani 1 1 d . . .
H15A H 0.2068 0.1792 0.8989 0.040 Uiso 1 1 calc R . .
H15B H 0.2071 0.2804 0.8677 0.040 Uiso 1 1 calc R . .
H15C H 0.3580 0.2257 0.8739 0.040 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
O 0.0385(6) 0.0655(8) 0.0229(6) -0.0064(5) -0.0084(5) 0.0063(6)
N1 0.0226(5) 0.0291(6) 0.0252(6) -0.0050(5) -0.0036(5) 0.0031(5)
N2 0.0214(5) 0.0233(6) 0.0190(5) -0.0022(4) -0.0007(4) 0.0017(4)
C1 0.0244(6) 0.0361(8) 0.0229(7) -0.0046(6) -0.0019(5) 0.0106(6)
C2 0.0262(6) 0.0271(7) 0.0240(7) 0.0020(6) 0.0027(5) 0.0118(6)
C3 0.0393(8) 0.0384(9) 0.0260(7) 0.0065(6) 0.0095(6) 0.0169(7)
C4 0.0425(9) 0.0379(9) 0.0423(10) 0.0143(7) 0.0216(8) 0.0124(8)
C5 0.0342(8) 0.0298(8) 0.0533(11) 0.0048(7) 0.0156(7) 0.0013(7)
C6 0.0298(7) 0.0270(7) 0.0363(8) -0.0011(6) 0.0053(6) 0.0002(6)
C7 0.0217(6) 0.0235(7) 0.0253(7) 0.0010(5) 0.0035(5) 0.0065(5)
C8 0.0163(5) 0.0224(6) 0.0241(7) -0.0030(5) -0.0001(5) 0.0041(5)
C9 0.0216(6) 0.0202(6) 0.0260(7) -0.0030(5) 0.0025(5) 0.0030(5)
C10 0.0257(7) 0.0274(7) 0.0262(7) -0.0010(6) 0.0005(5) 0.0049(6)
C11 0.0410(8) 0.0314(8) 0.0279(8) 0.0029(6) 0.0037(6) 0.0119(7)
C12 0.0506(10) 0.0279(8) 0.0392(9) 0.0062(7) 0.0181(8) 0.0055(7)
C13 0.0311(8) 0.0292(8) 0.0525(10) -0.0005(7) 0.0134(7) -0.0033(6)
C14 0.0229(7) 0.0262(7) 0.0391(8) -0.0032(6) 0.0023(6) 0.0020(6)
C15 0.0288(7) 0.0288(7) 0.0217(7) -0.0058(5) -0.0013(5) -0.0009(6)

_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
O C1 1.2322(17) . ?
N1 C8 1.3111(17) . ?
N1 C1 1.383(2) . ?
N2 C8 1.3638(17) . ?
N2 C7 1.3989(18) . ?
N2 C15 1.4743(17) . ?
C1 C2 1.466(2) . ?
C2 C3 1.403(2) . ?
C2 C7 1.404(2) . ?
C3 C4 1.376(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.398(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.379(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.403(2) . ?
C6 H6A 0.9500 . ?
C8 C9 1.4879(19) . ?
C9 C14 1.3951(19) . ?
C9 C10 1.3994(19) . ?
C10 C11 1.388(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.390(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.383(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.385(2) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C8 N1 C1 119.92(12) . . ?
C8 N2 C7 118.68(11) . . ?
C8 N2 C15 122.31(11) . . ?
C7 N2 C15 118.82(11) . . ?
O C1 N1 120.23(14) . . ?
O C1 C2 122.38(14) . . ?
N1 C1 C2 117.38(12) . . ?
C3 C2 C7 119.24(14) . . ?
C3 C2 C1 121.56(14) . . ?
C7 C2 C1 119.13(13) . . ?
C4 C3 C2 120.82(15) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 119.31(15) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
C6 C5 C4 121.30(16) . . ?
C6 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
C5 C6 C7 119.42(15) . . ?
C5 C6 H6A 120.3 . . ?
C7 C6 H6A 120.3 . . ?
N2 C7 C6 121.84(13) . . ?
N2 C7 C2 118.30(13) . . ?
C6 C7 C2 119.85(13) . . ?
N1 C8 N2 124.94(13) . . ?
N1 C8 C9 115.90(12) . . ?
N2 C8 C9 119.12(11) . . ?
C14 C9 C10 119.54(13) . . ?
C14 C9 C8 118.59(12) . . ?
C10 C9 C8 121.66(12) . . ?
C11 C10 C9 119.84(14) . . ?
C11 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
C10 C11 C12 120.09(15) . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C13 C12 C11 120.20(15) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C12 C13 C14 120.13(15) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C13 C14 C9 120.18(14) . . ?
C13 C14 H14A 119.9 . . ?
C9 C14 H14A 119.9 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.884
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_ck290
_database_code_depnum_ccdc_archive 'CCDC 1468854'
_audit_update_record             
;
2016-04-30 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;

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

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            'Light yellow'

_diffrn_ambient_temperature      150(2)
_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   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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                   6.2999(6)
_cell_length_b                   19.429(2)
_cell_length_c                   9.8817(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.092(10)
_cell_angle_gamma                90.00
_cell_volume                     1197.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1309
_cell_measurement_theta_min      3.4130
_cell_measurement_theta_max      28.2750
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92939
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) 
(compiled Dec  3 2012,18:21:49) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5033
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0611
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         29.17
_reflns_number_total             2751
_reflns_number_gt                1974
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0705P)²+0.6307P] 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         2751
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1741
_refine_ls_wR_factor_gt          0.1512
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.003

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
O O 0.4330(3) 0.42716(9) 0.61424(16) 0.0294(4) Uani 1 1 d . . .
H0A H 0.5187 0.4605 0.6186 0.044 Uiso 1 1 calc R . .
N1 N 0.3028(3) 0.32671(10) 0.32531(18) 0.0233(4) Uani 1 1 d . . .
N2 N 0.3625(3) 0.44484(10) 0.37675(18) 0.0239(4) Uani 1 1 d . . .
C1 C 0.1445(3) 0.32162(11) 0.4123(2) 0.0212(5) Uani 1 1 d . . .
C2 C 0.0106(4) 0.26379(13) 0.4113(2) 0.0280(5) Uani 1 1 d . . .
H2B H 0.0299 0.2255 0.3545 0.034 Uiso 1 1 calc R . .
C3 C -0.1503(4) 0.26308(14) 0.4940(3) 0.0324(6) Uani 1 1 d . . .
H3A H -0.2393 0.2237 0.4949 0.039 Uiso 1 1 calc R . .
C4 C -0.1824(4) 0.31900(14) 0.5747(3) 0.0326(6) Uani 1 1 d . . .
H4A H -0.2963 0.3187 0.6284 0.039 Uiso 1 1 calc R . .
C5 C -0.0480(4) 0.37578(13) 0.5774(2) 0.0275(5) Uani 1 1 d . . .
H5A H -0.0697 0.4141 0.6335 0.033 Uiso 1 1 calc R . .
C6 C 0.1184(3) 0.37689(12) 0.4985(2) 0.0219(5) Uani 1 1 d . . .
C7 C 0.2694(4) 0.43682(12) 0.5037(2) 0.0247(5) Uani 1 1 d . . .
H7A H 0.2384 0.4797 0.5590 0.050 Uiso 1 1 d . . .
C8 C 0.3856(3) 0.39091(11) 0.3042(2) 0.0208(5) Uani 1 1 d . . .
C9 C 0.5044(4) 0.40018(12) 0.1842(2) 0.0230(5) Uani 1 1 d . . .
C10 C 0.7148(4) 0.42330(13) 0.2053(3) 0.0289(5) Uani 1 1 d . . .
H10A H 0.7864 0.4297 0.2956 0.035 Uiso 1 1 calc R . .
C11 C 0.8205(5) 0.43701(14) 0.0939(3) 0.0387(7) Uani 1 1 d . . .
H11A H 0.9653 0.4522 0.1079 0.046 Uiso 1 1 calc R . .
C12 C 0.7149(5) 0.42855(13) -0.0372(3) 0.0398(7) Uani 1 1 d . . .
H12A H 0.7869 0.4385 -0.1131 0.048 Uiso 1 1 calc R . .
C13 C 0.5050(5) 0.40568(13) -0.0587(2) 0.0361(6) Uani 1 1 d . . .
H13A H 0.4331 0.4003 -0.1493 0.043 Uiso 1 1 calc R . .
C14 C 0.3992(4) 0.39053(12) 0.0515(2) 0.0274(5) Uani 1 1 d . . .
H14A H 0.2562 0.3737 0.0368 0.033 Uiso 1 1 calc R . .
C15 C 0.3623(4) 0.26522(12) 0.2538(2) 0.0294(5) Uani 1 1 d . . .
H15A H 0.4733 0.2771 0.1976 0.044 Uiso 1 1 calc R . .
H15B H 0.2360 0.2473 0.1951 0.044 Uiso 1 1 calc R . .
H15C H 0.4174 0.2301 0.3208 0.044 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
O 0.0351(9) 0.0303(10) 0.0227(8) 0.0014(7) 0.0033(7) -0.0042(8)
N1 0.0280(10) 0.0229(10) 0.0195(9) -0.0012(7) 0.0053(8) -0.0012(8)
N2 0.0295(10) 0.0250(10) 0.0178(9) -0.0017(8) 0.0057(8) -0.0075(8)
C1 0.0217(10) 0.0231(11) 0.0179(10) 0.0042(9) -0.0006(8) 0.0002(9)
C2 0.0296(12) 0.0242(12) 0.0289(12) 0.0004(10) -0.0009(10) -0.0037(10)
C3 0.0245(12) 0.0319(13) 0.0399(14) 0.0104(11) 0.0013(10) -0.0080(11)
C4 0.0246(12) 0.0369(14) 0.0380(14) 0.0120(12) 0.0104(10) 0.0012(11)
C5 0.0292(12) 0.0276(12) 0.0274(12) 0.0052(10) 0.0100(10) 0.0041(10)
C6 0.0245(11) 0.0232(11) 0.0178(10) 0.0035(9) 0.0019(8) 0.0001(9)
C7 0.0326(12) 0.0244(12) 0.0183(10) -0.0028(9) 0.0078(9) -0.0046(10)
C8 0.0227(10) 0.0232(11) 0.0158(10) 0.0002(9) 0.0005(8) -0.0021(9)
C9 0.0291(11) 0.0220(11) 0.0190(11) 0.0017(9) 0.0069(9) 0.0026(9)
C10 0.0284(12) 0.0307(13) 0.0280(12) 0.0026(10) 0.0060(10) 0.0018(10)
C11 0.0384(14) 0.0321(14) 0.0503(16) 0.0015(12) 0.0232(13) -0.0008(12)
C12 0.0649(19) 0.0284(13) 0.0328(14) 0.0022(11) 0.0304(14) 0.0018(13)
C13 0.0656(18) 0.0252(13) 0.0192(11) 0.0014(10) 0.0122(12) 0.0080(13)
C14 0.0355(13) 0.0255(12) 0.0210(11) -0.0005(9) 0.0035(10) 0.0039(10)
C15 0.0381(13) 0.0232(12) 0.0271(12) -0.0029(10) 0.0054(10) 0.0024(11)

_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
O C7 1.405(3) . ?
O H0A 0.8400 . ?
N1 C8 1.379(3) . ?
N1 C1 1.409(3) . ?
N1 C15 1.463(3) . ?
N2 C8 1.289(3) . ?
N2 C7 1.466(3) . ?
C1 C6 1.395(3) . ?
C1 C2 1.404(3) . ?
C2 C3 1.389(3) . ?
C2 H2B 0.9500 . ?
C3 C4 1.380(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.392(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.500(3) . ?
C7 H7A 1.0300 . ?
C8 C9 1.500(3) . ?
C9 C10 1.387(3) . ?
C9 C14 1.397(3) . ?
C10 C11 1.391(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.380(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.383(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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 O H0A 109.5 . . ?
C8 N1 C1 118.08(18) . . ?
C8 N1 C15 122.54(18) . . ?
C1 N1 C15 119.24(19) . . ?
C8 N2 C7 118.63(18) . . ?
C6 C1 C2 119.9(2) . . ?
C6 C1 N1 118.2(2) . . ?
C2 C1 N1 121.9(2) . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2B 120.3 . . ?
C1 C2 H2B 120.3 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 C7 121.1(2) . . ?
C1 C6 C7 119.34(19) . . ?
O C7 N2 109.98(18) . . ?
O C7 C6 108.39(18) . . ?
N2 C7 C6 112.41(18) . . ?
O C7 H7A 82.5 . . ?
N2 C7 H7A 119.8 . . ?
C6 C7 H7A 118.6 . . ?
N2 C8 N1 125.23(19) . . ?
N2 C8 C9 116.73(19) . . ?
N1 C8 C9 117.99(18) . . ?
C10 C9 C14 120.1(2) . . ?
C10 C9 C8 119.5(2) . . ?
C14 C9 C8 120.2(2) . . ?
C9 C10 C11 119.8(2) . . ?
C9 C10 H10A 120.1 . . ?
C11 C10 H10A 120.1 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C13 C14 C9 119.5(2) . . ?
C13 C14 H14A 120.3 . . ?
C9 C14 H14A 120.3 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.851
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.058

