# 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_c2_4_ome
_database_code_depnum_ccdc_archive 'CCDC 1451741'
_audit_update_record             
;
2016-02-03 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31

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           Orthorhombic
_symmetry_space_group_name_H-M   'Pna2(1) '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   7.8517(10)
_cell_length_b                   14.459(2)
_cell_length_c                   11.5168(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1307.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2843
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      22.20

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9627
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_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-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10358
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_sigmaI/netI    0.0611
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         24.98
_reflns_number_total             2295
_reflns_number_gt                1970
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0829P)²+0.2019P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_number_reflns         2295
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1581
_refine_ls_wR_factor_gt          0.1508
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.109
_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
O1 O 0.0021(4) 0.66217(18) 0.5838(3) 0.0547(8) Uani 1 1 d . . .
O2 O 0.2454(4) 0.52094(17) 0.2540(3) 0.0553(8) Uani 1 1 d . . .
N1 N 0.1306(4) 0.65572(18) 0.1799(3) 0.0340(7) Uani 1 1 d . . .
N2 N 0.1661(4) 0.9333(2) 0.1316(3) 0.0420(8) Uani 1 1 d . . .
C1 C -0.0807(6) 0.7043(3) 0.6788(4) 0.0562(11) Uani 1 1 d . . .
H1A H -0.0053 0.7482 0.7145 0.084 Uiso 1 1 calc R . .
H1B H -0.1118 0.6579 0.7345 0.084 Uiso 1 1 calc R . .
H1C H -0.1812 0.7355 0.6521 0.084 Uiso 1 1 calc R . .
C2 C 0.0266(5) 0.7126(2) 0.4845(3) 0.0390(8) Uani 1 1 d . . .
C3 C 0.0200(5) 0.8083(2) 0.4794(3) 0.0409(9) Uani 1 1 d . . .
H3 H -0.0054 0.8426 0.5455 0.049 Uiso 1 1 calc R . .
C4 C 0.0515(5) 0.8521(2) 0.3751(3) 0.0420(9) Uani 1 1 d . . .
H4 H 0.0449 0.9163 0.3722 0.050 Uiso 1 1 calc R . .
C5 C 0.0922(4) 0.8049(2) 0.2752(3) 0.0329(8) Uani 1 1 d . . .
C6 C 0.0972(4) 0.7063(2) 0.2826(3) 0.0310(8) Uani 1 1 d . . .
C7 C 0.0641(5) 0.6623(2) 0.3858(3) 0.0376(8) Uani 1 1 d . . .
H7 H 0.0670 0.5981 0.3893 0.045 Uiso 1 1 calc R . .
C8 C 0.2004(4) 0.5690(2) 0.1719(3) 0.0383(8) Uani 1 1 d . . .
C9 C 0.2106(6) 0.5430(3) 0.0453(3) 0.0493(10) Uani 1 1 d . . .
H9A H 0.1281 0.4953 0.0269 0.059 Uiso 1 1 calc R . .
H9B H 0.3236 0.5205 0.0260 0.059 Uiso 1 1 calc R . .
C10 C 0.1718(5) 0.6306(3) -0.0202(4) 0.0496(10) Uani 1 1 d . . .
H10A H 0.1020 0.6176 -0.0878 0.060 Uiso 1 1 calc R . .
H10B H 0.2760 0.6604 -0.0455 0.060 Uiso 1 1 calc R . .
C11 C 0.0754(4) 0.6921(2) 0.0660(3) 0.0355(8) Uani 1 1 d . . .
H11 H -0.0475 0.6828 0.0568 0.043 Uiso 1 1 calc R . .
C12 C 0.1151(4) 0.7927(2) 0.0605(3) 0.0364(8) Uani 1 1 d . . .
C13 C 0.1238(4) 0.8432(2) 0.1605(3) 0.0328(8) Uani 1 1 d . . .
C14 C 0.2024(6) 1.0097(3) 0.2106(4) 0.0614(12) Uani 1 1 d . . .
H14A H 0.2544 1.0595 0.1682 0.092 Uiso 1 1 calc R . .
H14B H 0.2786 0.9891 0.2704 0.092 Uiso 1 1 calc R . .
H14C H 0.0982 1.0310 0.2451 0.092 Uiso 1 1 calc R . .
C15 C 0.1797(5) 0.9388(3) 0.0150(3) 0.0436(10) Uani 1 1 d . . .
H15 H 0.2059 0.9921 -0.0265 0.052 Uiso 1 1 calc R . .
C16 C 0.1488(5) 0.8537(3) -0.0325(3) 0.0424(9) Uani 1 1 d . . .
H16 H 0.1498 0.8389 -0.1111 0.051 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 C2 1.370(5) . ?
O1 C1 1.411(5) . ?
O2 C8 1.226(4) . ?
N1 C8 1.372(4) . ?
N1 C6 1.416(5) . ?
N1 C11 1.478(5) . ?
N2 C15 1.349(5) . ?
N2 C13 1.384(4) . ?
N2 C14 1.460(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.381(5) . ?
C2 C3 1.385(5) . ?
C3 C4 1.380(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.428(5) . ?
C5 C13 1.455(5) . ?
C6 C7 1.372(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.507(5) . ?
C9 C10 1.505(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.533(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.489(5) . ?
C11 H11 0.9800 . ?
C12 C13 1.365(5) . ?
C12 C16 1.413(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.368(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 118.8(3) . . ?
C8 N1 C6 127.0(3) . . ?
C8 N1 C11 112.5(3) . . ?
C6 N1 C11 120.2(3) . . ?
C15 N2 C13 108.3(3) . . ?
C15 N2 C14 124.0(3) . . ?
C13 N2 C14 127.6(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 115.8(3) . . ?
O1 C2 C3 124.2(3) . . ?
C7 C2 C3 120.0(3) . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 122.8(3) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C4 C5 C6 116.9(3) . . ?
C4 C5 C13 127.6(3) . . ?
C6 C5 C13 115.5(3) . . ?
C7 C6 N1 121.3(3) . . ?
C7 C6 C5 120.6(3) . . ?
N1 C6 C5 118.1(3) . . ?
C6 C7 C2 120.6(3) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
O2 C8 N1 125.5(3) . . ?
O2 C8 C9 126.2(3) . . ?
N1 C8 C9 108.3(3) . . ?
C8 C9 C10 105.4(3) . . ?
C8 C9 H9A 110.7 . . ?
C10 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
C10 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
C9 C10 C11 105.3(3) . . ?
C9 C10 H10A 110.7 . . ?
C11 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
C11 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
N1 C11 C12 108.9(3) . . ?
N1 C11 C10 102.9(3) . . ?
C12 C11 C10 115.9(3) . . ?
N1 C11 H11 109.6 . . ?
C12 C11 H11 109.6 . . ?
C10 C11 H11 109.6 . . ?
C13 C12 C16 107.2(3) . . ?
C13 C12 C11 119.8(3) . . ?
C16 C12 C11 132.9(4) . . ?
C12 C13 N2 108.2(3) . . ?
C12 C13 C5 123.6(3) . . ?
N2 C13 C5 128.1(3) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C16 109.3(3) . . ?
N2 C15 H15 125.4 . . ?
C16 C15 H15 125.4 . . ?
C15 C16 C12 106.9(4) . . ?
C15 C16 H16 126.5 . . ?
C12 C16 H16 126.5 . . ?

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
C1 O1 C2 C7 -162.9(4) . . . . ?
C1 O1 C2 C3 18.7(5) . . . . ?
O1 C2 C3 C4 178.2(4) . . . . ?
C7 C2 C3 C4 -0.1(5) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C3 C4 C5 C6 1.4(5) . . . . ?
C3 C4 C5 C13 178.4(4) . . . . ?
C8 N1 C6 C7 -27.8(5) . . . . ?
C11 N1 C6 C7 146.6(3) . . . . ?
C8 N1 C6 C5 154.5(3) . . . . ?
C11 N1 C6 C5 -31.1(4) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C13 C5 C6 C7 -178.0(3) . . . . ?
C4 C5 C6 N1 177.0(3) . . . . ?
C13 C5 C6 N1 -0.4(4) . . . . ?
N1 C6 C7 C2 -178.0(3) . . . . ?
C5 C6 C7 C2 -0.4(5) . . . . ?
O1 C2 C7 C6 -177.6(3) . . . . ?
C3 C2 C7 C6 0.8(6) . . . . ?
C6 N1 C8 O2 0.0(6) . . . . ?
C11 N1 C8 O2 -174.8(3) . . . . ?
C6 N1 C8 C9 179.6(3) . . . . ?
C11 N1 C8 C9 4.8(4) . . . . ?
O2 C8 C9 C10 -169.7(4) . . . . ?
N1 C8 C9 C10 10.8(4) . . . . ?
C8 C9 C10 C11 -21.3(4) . . . . ?
C8 N1 C11 C12 -141.4(3) . . . . ?
C6 N1 C11 C12 43.5(4) . . . . ?
C8 N1 C11 C10 -17.9(4) . . . . ?
C6 N1 C11 C10 166.9(3) . . . . ?
C9 C10 C11 N1 23.5(4) . . . . ?
C9 C10 C11 C12 142.1(3) . . . . ?
N1 C11 C12 C13 -26.6(4) . . . . ?
C10 C11 C12 C13 -142.0(3) . . . . ?
N1 C11 C12 C16 153.5(3) . . . . ?
C10 C11 C12 C16 38.1(5) . . . . ?
C16 C12 C13 N2 -1.4(4) . . . . ?
C11 C12 C13 N2 178.6(3) . . . . ?
C16 C12 C13 C5 178.4(3) . . . . ?
C11 C12 C13 C5 -1.5(5) . . . . ?
C15 N2 C13 C12 1.3(4) . . . . ?
C14 N2 C13 C12 -174.8(4) . . . . ?
C15 N2 C13 C5 -178.5(3) . . . . ?
C14 N2 C13 C5 5.4(6) . . . . ?
C4 C5 C13 C12 -160.4(4) . . . . ?
C6 C5 C13 C12 16.7(5) . . . . ?
C4 C5 C13 N2 19.4(6) . . . . ?
C6 C5 C13 N2 -163.5(3) . . . . ?
C13 N2 C15 C16 -0.6(4) . . . . ?
C14 N2 C15 C16 175.6(3) . . . . ?
N2 C15 C16 C12 -0.2(4) . . . . ?
C13 C12 C16 C15 1.0(4) . . . . ?
C11 C12 C16 C15 -179.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.054
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent:  Dichloromethane-pet ether mixture'
####################################################################### 
# 
# 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_indra280715_0m
_database_code_depnum_ccdc_archive 'CCDC 1451742'
_audit_update_record             
;
2016-02-03 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 N3 O'
_chemical_formula_sum            'C18 H15 N3 O'
_chemical_formula_weight         289.33

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                   8.0565(17)
_cell_length_b                   9.148(2)
_cell_length_c                   10.828(2)
_cell_angle_alpha                79.929(14)
_cell_angle_beta                 71.859(13)
_cell_angle_gamma                66.783(13)
_cell_volume                     695.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3633
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      32.46

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_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-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5450
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0698
_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       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2396
_reflns_number_gt                1999
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.1117P)²+0.0520P] 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         2396
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1776
_refine_ls_wR_factor_gt          0.1674
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
O1 O 0.8103(2) 0.94607(17) 0.49555(15) 0.0570(5) Uani 1 1 d . . .
N1 N 1.0307(2) 0.2885(2) 0.20455(16) 0.0438(5) Uani 1 1 d . . .
N2 N 0.6693(2) 0.76117(18) 0.56906(15) 0.0365(4) Uani 1 1 d . . .
N3 N 0.6542(2) 0.46397(18) 0.63567(15) 0.0396(4) Uani 1 1 d . . .
C1 C 1.1262(4) 0.3060(3) 0.0772(2) 0.0746(8) Uani 1 1 d . . .
H1 H 1.1545 0.3953 0.0379 0.090 Uiso 1 1 calc R . .
C2 C 1.1725(4) 0.1710(3) 0.0183(2) 0.0797(8) Uani 1 1 d . . .
H2 H 1.2381 0.1515 -0.0682 0.096 Uiso 1 1 calc R . .
C3 C 1.1050(3) 0.0671(3) 0.1097(2) 0.0601(6) Uani 1 1 d . . .
H3 H 1.1165 -0.0343 0.0956 0.072 Uiso 1 1 calc R . .
C4 C 1.0190(3) 0.1406(3) 0.2235(2) 0.0501(6) Uani 1 1 d . . .
H4 H 0.9617 0.0976 0.3014 0.060 Uiso 1 1 calc R . .
C5 C 0.9468(2) 0.4081(2) 0.29655(18) 0.0376(5) Uani 1 1 d . . .
C6 C 0.9670(3) 0.5541(2) 0.26521(19) 0.0452(5) Uani 1 1 d . . .
H6 H 1.0414 0.5735 0.1840 0.054 Uiso 1 1 calc R . .
C7 C 0.8780(3) 0.6713(2) 0.35311(19) 0.0429(5) Uani 1 1 d . . .
H7 H 0.8919 0.7694 0.3301 0.052 Uiso 1 1 calc R . .
C8 C 0.7680(2) 0.6451(2) 0.47532(17) 0.0339(4) Uani 1 1 d . . .
C9 C 0.7542(2) 0.4953(2) 0.50835(17) 0.0339(4) Uani 1 1 d . . .
C10 C 0.8413(2) 0.3785(2) 0.41955(18) 0.0379(5) Uani 1 1 d . . .
H10 H 0.8290 0.2797 0.4424 0.045 Uiso 1 1 calc R . .
C11 C 0.6936(3) 0.8990(2) 0.57397(19) 0.0405(5) Uani 1 1 d . . .
C12 C 0.5499(3) 0.9825(2) 0.6909(2) 0.0484(5) Uani 1 1 d . . .
H12A H 0.4579 1.0790 0.6642 0.058 Uiso 1 1 calc R . .
H12B H 0.6095 1.0109 0.7435 0.058 Uiso 1 1 calc R . .
C13 C 0.4577(3) 0.8675(3) 0.7672(2) 0.0537(6) Uani 1 1 d . . .
H13A H 0.3237 0.9221 0.8009 0.064 Uiso 1 1 calc R . .
H13B H 0.5108 0.8138 0.8392 0.064 Uiso 1 1 calc R . .
C14 C 0.4994(2) 0.7495(2) 0.66736(19) 0.0416(5) Uani 1 1 d . . .
H14 H 0.3956 0.7844 0.6270 0.050 Uiso 1 1 calc R . .
C15 C 0.5365(3) 0.5832(2) 0.71934(19) 0.0415(5) Uani 1 1 d . . .
C16 C 0.4713(3) 0.5131(3) 0.8355(2) 0.0605(6) Uani 1 1 d . . .
H16 H 0.3880 0.5650 0.9095 0.073 Uiso 1 1 calc R . .
C17 C 0.5528(4) 0.3482(3) 0.8235(2) 0.0726(8) Uani 1 1 d . . .
H17 H 0.5333 0.2711 0.8887 0.087 Uiso 1 1 calc R . .
C18 C 0.6645(3) 0.3202(3) 0.7012(2) 0.0573(6) Uani 1 1 d . . .
H18 H 0.7357 0.2206 0.6676 0.069 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 C11 1.219(2) . ?
N1 C1 1.371(3) . ?
N1 C4 1.369(3) . ?
N1 C5 1.423(3) . ?
N2 C11 1.362(2) . ?
N2 C8 1.414(2) . ?
N2 C14 1.479(2) . ?
N3 C18 1.366(3) . ?
N3 C15 1.380(2) . ?
N3 C9 1.409(2) . ?
C1 C2 1.355(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(3) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.381(3) . ?
C5 C10 1.385(3) . ?
C6 C7 1.376(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.386(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(3) . ?
C9 C10 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.502(3) . ?
C12 C13 1.507(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.531(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.472(3) . ?
C14 H14 0.9800 . ?
C15 C16 1.357(3) . ?
C16 C17 1.399(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.351(3) . ?
C17 H17 0.9300 . ?
C18 H18 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
C1 N1 C4 107.58(18) . . ?
C1 N1 C5 125.65(19) . . ?
C4 N1 C5 126.60(17) . . ?
C11 N2 C8 128.80(16) . . ?
C11 N2 C14 112.13(15) . . ?
C8 N2 C14 118.51(14) . . ?
C18 N3 C15 108.65(16) . . ?
C18 N3 C9 128.67(16) . . ?
C15 N3 C9 122.48(16) . . ?
C2 C1 N1 108.3(2) . . ?
C2 C1 H1 125.8 . . ?
N1 C1 H1 125.8 . . ?
C1 C2 C3 108.0(2) . . ?
C1 C2 H2 126.0 . . ?
C3 C2 H2 126.0 . . ?
C4 C3 C2 107.3(2) . . ?
C4 C3 H3 126.3 . . ?
C2 C3 H3 126.3 . . ?
C3 C4 N1 108.7(2) . . ?
C3 C4 H4 125.6 . . ?
N1 C4 H4 125.6 . . ?
C6 C5 C10 119.17(18) . . ?
C6 C5 N1 121.18(18) . . ?
C10 C5 N1 119.65(18) . . ?
C7 C6 C5 120.56(18) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.97(19) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C9 118.21(18) . . ?
C7 C8 N2 123.90(17) . . ?
C9 C8 N2 117.89(16) . . ?
C10 C9 C8 120.81(17) . . ?
C10 C9 N3 120.63(16) . . ?
C8 C9 N3 118.53(16) . . ?
C9 C10 C5 120.20(18) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
O1 C11 N2 125.48(19) . . ?
O1 C11 C12 126.48(17) . . ?
N2 C11 C12 108.03(16) . . ?
C11 C12 C13 106.53(15) . . ?
C11 C12 H12A 110.4 . . ?
C13 C12 H12A 110.4 . . ?
C11 C12 H12B 110.4 . . ?
C13 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C12 C13 C14 103.82(17) . . ?
C12 C13 H13A 111.0 . . ?
C14 C13 H13A 111.0 . . ?
C12 C13 H13B 111.0 . . ?
C14 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
C15 C14 N2 109.48(15) . . ?
C15 C14 C13 114.82(17) . . ?
N2 C14 C13 103.67(15) . . ?
C15 C14 H14 109.6 . . ?
N2 C14 H14 109.6 . . ?
C13 C14 H14 109.6 . . ?
C16 C15 N3 107.74(18) . . ?
C16 C15 C14 134.22(18) . . ?
N3 C15 C14 117.92(16) . . ?
C15 C16 C17 107.3(2) . . ?
C15 C16 H16 126.3 . . ?
C17 C16 H16 126.3 . . ?
C18 C17 C16 108.4(2) . . ?
C18 C17 H17 125.8 . . ?
C16 C17 H17 125.8 . . ?
C17 C18 N3 107.8(2) . . ?
C17 C18 H18 126.1 . . ?
N3 C18 H18 126.1 . . ?

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
C4 N1 C1 C2 0.1(3) . . . . ?
C5 N1 C1 C2 -175.4(2) . . . . ?
N1 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 N1 0.4(3) . . . . ?
C1 N1 C4 C3 -0.3(3) . . . . ?
C5 N1 C4 C3 175.16(17) . . . . ?
C1 N1 C5 C6 -4.5(3) . . . . ?
C4 N1 C5 C6 -179.24(18) . . . . ?
C1 N1 C5 C10 174.9(2) . . . . ?
C4 N1 C5 C10 0.2(3) . . . . ?
C10 C5 C6 C7 -2.4(3) . . . . ?
N1 C5 C6 C7 177.00(16) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C6 C7 C8 C9 1.9(3) . . . . ?
C6 C7 C8 N2 -178.48(15) . . . . ?
C11 N2 C8 C7 -16.9(3) . . . . ?
C14 N2 C8 C7 153.85(17) . . . . ?
C11 N2 C8 C9 162.79(17) . . . . ?
C14 N2 C8 C9 -26.5(2) . . . . ?
C7 C8 C9 C10 -2.8(3) . . . . ?
N2 C8 C9 C10 177.50(14) . . . . ?
C7 C8 C9 N3 175.33(15) . . . . ?
N2 C8 C9 N3 -4.3(2) . . . . ?
C18 N3 C9 C10 18.4(3) . . . . ?
C15 N3 C9 C10 -167.41(16) . . . . ?
C18 N3 C9 C8 -159.76(19) . . . . ?
C15 N3 C9 C8 14.4(2) . . . . ?
C8 C9 C10 C5 1.2(3) . . . . ?
N3 C9 C10 C5 -176.92(15) . . . . ?
C6 C5 C10 C9 1.4(3) . . . . ?
N1 C5 C10 C9 -177.98(14) . . . . ?
C8 N2 C11 O1 -0.7(3) . . . . ?
C14 N2 C11 O1 -171.86(17) . . . . ?
C8 N2 C11 C12 178.45(16) . . . . ?
C14 N2 C11 C12 7.3(2) . . . . ?
O1 C11 C12 C13 -172.07(19) . . . . ?
N2 C11 C12 C13 8.8(2) . . . . ?
C11 C12 C13 C14 -20.3(2) . . . . ?
C11 N2 C14 C15 -142.93(16) . . . . ?
C8 N2 C14 C15 44.9(2) . . . . ?
C11 N2 C14 C13 -20.0(2) . . . . ?
C8 N2 C14 C13 167.85(15) . . . . ?
C12 C13 C14 C15 143.16(17) . . . . ?
C12 C13 C14 N2 23.8(2) . . . . ?
C18 N3 C15 C16 -1.2(2) . . . . ?
C9 N3 C15 C16 -176.42(17) . . . . ?
C18 N3 C15 C14 -177.79(17) . . . . ?
C9 N3 C15 C14 7.0(2) . . . . ?
N2 C14 C15 C16 150.0(2) . . . . ?
C13 C14 C15 C16 34.0(3) . . . . ?
N2 C14 C15 N3 -34.5(2) . . . . ?
C13 C14 C15 N3 -150.57(16) . . . . ?
N3 C15 C16 C17 1.0(3) . . . . ?
C14 C15 C16 C17 176.8(2) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C17 C18 N3 -0.4(3) . . . . ?
C15 N3 C18 C17 1.0(3) . . . . ?
C9 N3 C18 C17 175.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.066


#===

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent:  Dichloromethane-pet ether mixture'
