# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_4c
_database_code_depnum_ccdc_archive 'CCDC 2253075'
loop_
_audit_author_name
_audit_author_address
'Attila Benyei'
;University of Debrecen
Hungary
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_publcif_datablock.id            {a19d3a49-5aa6-4280-bb8a-c01665e751f9}

_audit_creation_date             2011-02-08T10:57:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 N3 O'
_chemical_formula_sum            'C21 H19 N3 O'
_chemical_formula_weight         329.39

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.317(5)
_cell_length_b                   8.519(5)
_cell_length_c                   19.641(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 127.830(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     3610(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      4.7
_cell_measurement_theta_max      11.5
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'profiled omega/2theta scans'
_diffrn_reflns_number            3725
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         25.52
_diffrn_reflns_theta_full        25.52
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         4
_diffrn_standards_interval_count 102
_diffrn_standards_interval_time  5
_diffrn_standards_decay_%        4
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-6 -4 6
1 -3 -3
0 -2 -1
7 -1 -3


#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_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 > 2σ(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.
;
_reflns_number_total             3725
_reflns_number_gt                1955
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.1909
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_number_reflns         3725
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0586P)²+19.9399P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.35
_refine_diff_density_rms         0.07
_refine_ls_extinction_method     none
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1992)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1992)'
_computing_data_reduction        'PROFIT (Streltsov & Zavodnik, 1989)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.4624(4) 0.3095(8) -0.5300(4) 0.077(2) Uani d . 1 . . C
C2 0.4442(4) 0.0593(9) -0.4920(4) 0.072(2) Uani d . 1 . . C
C3 0.4778(3) 0.1998(7) -0.4631(4) 0.0616(17) Uani d . 1 . . C
C4 0.5235(3) 0.2395(7) -0.3806(4) 0.0620(17) Uani d . 1 . . C
H4 0.5403 0.3393 -0.3713 0.074 Uiso calc . 1 . . H
C5 0.5493(3) 0.1421(7) -0.3046(4) 0.0570(16) Uani d . 1 . . C
C6 0.5509(4) -0.0212(8) -0.3071(4) 0.082(2) Uani d . 1 . . C
H6 0.5341 -0.0714 -0.3592 0.099 Uiso calc . 1 . . H
C7 0.5774(4) -0.1102(8) -0.2329(5) 0.100(3) Uani d . 1 . . C
H7 0.5779 -0.2191 -0.2352 0.12 Uiso calc . 1 . . H
C8 0.6030(4) -0.0338(8) -0.1556(4) 0.088(3) Uani d . 1 . . C
H8 0.6215 -0.0926 -0.1055 0.106 Uiso calc . 1 . . H
C9 0.6018(3) 0.1253(8) -0.1513(4) 0.0634(17) Uani d . 1 . . C
H9 0.618 0.1744 -0.0991 0.076 Uiso calc . 1 . . H
C10 0.5765(3) 0.2130(7) -0.2245(4) 0.0544(15) Uani d . 1 . . C
C11 0.6083(3) 0.4527(7) -0.1473(4) 0.0536(15) Uani d . 1 . . C
C12 0.5787(3) 0.5188(7) -0.1161(4) 0.0694(18) Uani d . 1 . . C
H12 0.536 0.5101 -0.1474 0.083 Uiso calc . 1 . . H
C13 0.6137(4) 0.5971(8) -0.0382(5) 0.077(2) Uani d . 1 . . C
H13 0.5948 0.6406 -0.0162 0.093 Uiso calc . 1 . . H
C14 0.6751(4) 0.6099(8) 0.0056(4) 0.079(2) Uani d . 1 . . C
H14 0.6985 0.6608 0.0587 0.094 Uiso calc . 1 . . H
C15 0.7048(3) 0.5498(8) -0.0259(4) 0.076(2) Uani d . 1 . . C
H15 0.7473 0.563 0.0048 0.091 Uiso calc . 1 . . H
C16 0.6698(3) 0.4682(7) -0.1049(4) 0.0596(16) Uani d . 1 . . C
C17 0.6790(3) 0.4867(7) -0.2195(4) 0.072(2) Uani d . 1 . . C
H17A 0.6994 0.5881 -0.2036 0.087 Uiso calc R 1 . . H
H17B 0.6346 0.5038 -0.2579 0.087 Uiso calc R 1 . . H
C18 0.6980(4) 0.3892(10) -0.2650(5) 0.098(3) Uani d . 1 . . C
H18A 0.6741 0.2927 -0.2859 0.117 Uiso calc R 1 . . H
H18B 0.6882 0.4471 -0.3145 0.117 Uiso calc R 1 . . H
C19 0.7646(4) 0.3502(11) -0.2083(6) 0.111(3) Uani d . 1 . . C
H19A 0.7889 0.4452 -0.1931 0.133 Uiso calc R 1 . . H
H19B 0.7738 0.2807 -0.2383 0.133 Uiso calc R 1 . . H
C20 0.7815(4) 0.2707(10) -0.1273(6) 0.109(3) Uani d . 1 . . C
H20A 0.7608 0.1699 -0.142 0.131 Uiso calc R 1 . . H
H20B 0.8259 0.2525 -0.0879 0.131 Uiso calc R 1 . . H
C21 0.7625(3) 0.3721(9) -0.0840(4) 0.083(2) Uani d . 1 . . C
H21A 0.7732 0.3196 -0.0327 0.099 Uiso calc R 1 . . H
H21B 0.7849 0.4707 -0.0666 0.099 Uiso calc R 1 . . H
N1 0.4480(4) 0.3873(8) -0.5854(4) 0.109(2) Uani d . 1 . . N
N2 0.4149(3) -0.0502(8) -0.5195(4) 0.096(2) Uani d . 1 . . N
N3 0.6969(2) 0.4024(6) -0.1416(3) 0.0614(14) Uani d . 1 . . N
O1 0.57169(19) 0.3746(4) -0.2261(2) 0.0585(11) Uani d . 1 . . O



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.119(8) ?
C1 C3 . 1.449(8) ?
C2 N2 . 1.128(8) ?
C2 C3 . 1.400(9) ?
C3 C4 . 1.347(8) ?
C4 C5 . 1.457(8) ?
C4 H4 . 0.93 ?
C5 C6 . 1.394(8) ?
C5 C10 . 1.398(8) ?
C6 C7 . 1.388(9) ?
C6 H6 . 0.93 ?
C7 C8 . 1.384(9) ?
C7 H7 . 0.93 ?
C8 C9 . 1.360(9) ?
C8 H8 . 0.93 ?
C9 C10 . 1.373(8) ?
C9 H9 . 0.93 ?
C10 O1 . 1.382(6) ?
C11 C16 . 1.348(8) ?
C11 O1 . 1.393(7) ?
C11 C12 . 1.400(8) ?
C12 C13 . 1.380(9) ?
C12 H12 . 0.93 ?
C13 C14 . 1.342(10) ?
C13 H13 . 0.93 ?
C14 C15 . 1.385(10) ?
C14 H14 . 0.93 ?
C15 C16 . 1.410(9) ?
C15 H15 . 0.93 ?
C16 N3 . 1.425(7) ?
C17 N3 . 1.477(7) ?
C17 C18 . 1.525(9) ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
C18 C19 . 1.474(10) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C19 C20 . 1.517(10) ?
C19 H19A . 0.97 ?
C19 H19B . 0.97 ?
C20 C21 . 1.509(10) ?
C20 H20A . 0.97 ?
C20 H20B . 0.97 ?
C21 N3 . 1.440(8) ?
C21 H21A . 0.97 ?
C21 H21B . 0.97 ?

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
N1 C1 C3 175.6(8) . . ?
N2 C2 C3 176.3(9) . . ?
C4 C3 C2 126.6(6) . . ?
C4 C3 C1 117.9(6) . . ?
C2 C3 C1 115.5(6) . . ?
C3 C4 C5 126.8(6) . . ?
C3 C4 H4 116.6 . . ?
C5 C4 H4 116.6 . . ?
C6 C5 C10 117.6(6) . . ?
C6 C5 C4 122.5(6) . . ?
C10 C5 C4 119.7(5) . . ?
C7 C6 C5 121.0(6) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 118.8(6) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C9 C8 C7 121.5(6) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 119.5(6) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 O1 123.0(5) . . ?
C9 C10 C5 121.5(5) . . ?
O1 C10 C5 115.3(5) . . ?
C16 C11 O1 120.5(5) . . ?
C16 C11 C12 121.8(6) . . ?
O1 C11 C12 117.7(6) . . ?
C13 C12 C11 119.1(7) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 119.5(7) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 122.0(6) . . ?
C13 C14 H14 119 . . ?
C15 C14 H14 119 . . ?
C14 C15 C16 119.1(7) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 118.4(6) . . ?
C11 C16 N3 119.0(6) . . ?
C15 C16 N3 122.6(6) . . ?
N3 C17 C18 109.1(5) . . ?
N3 C17 H17A 109.9 . . ?
C18 C17 H17A 109.9 . . ?
N3 C17 H17B 109.9 . . ?
C18 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C19 C18 C17 112.7(6) . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 C20 109.5(7) . . ?
C18 C19 H19A 109.8 . . ?
C20 C19 H19A 109.8 . . ?
C18 C19 H19B 109.8 . . ?
C20 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
C21 C20 C19 110.3(6) . . ?
C21 C20 H20A 109.6 . . ?
C19 C20 H20A 109.6 . . ?
C21 C20 H20B 109.6 . . ?
C19 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
N3 C21 C20 110.7(6) . . ?
N3 C21 H21A 109.5 . . ?
C20 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C16 N3 C21 117.2(5) . . ?
C16 N3 C17 112.9(5) . . ?
C21 N3 C17 111.2(5) . . ?
C10 O1 C11 117.2(4) . . ?
####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 2253076'
loop_
_audit_author_name
_audit_author_address
'Attila Benyei'
;University of Debrecen
Hungary
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_publcif_datablock.id            {b98fa9eb-3a12-4137-b878-179bda4d783b}

_audit_creation_date             2011-02-08T11:22:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 N3 O'
_chemical_formula_sum            'C18 H15 N3 O'
_chemical_formula_weight         289.33
_chemical_absolute_configuration unk

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.7450(10)
_cell_length_b                   9.8360(10)
_cell_length_c                   17.5350(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1508.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.5
_cell_measurement_theta_max      18.4
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
        Number of psi-scan sets used was   2
        Theta correction was applied.
        Averaged transmission function was used.
        Fourier smoothing - Window value   5
;
_exptl_absorpt_correction_T_min  0.8556
_exptl_absorpt_correction_T_max  0.9456

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'profiled omega/2theta scans'
_diffrn_reflns_number            1767
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_theta_min         2.6
_diffrn_reflns_theta_max         25.96
_diffrn_reflns_theta_full        25.96
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         3
_diffrn_standards_interval_count 91
_diffrn_standards_interval_time  52
_diffrn_standards_decay_%        6
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 5 -7
-1 3 -8
-1 3 -6


#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_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 > 2σ(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.
;
_reflns_number_total             1710
_reflns_number_gt                1401
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1396
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_number_reflns         1710
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0585P)²+0.3772P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(4)
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1992)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1992)'
_computing_data_reduction        'PROFIT (Streltsov & Zavodnik, 1989)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.8214(5) 0.2694(5) 0.3534(2) 0.0615(12) Uani d . 1 . . C
C2 0.9261(5) 0.1662(4) 0.2429(2) 0.0544(10) Uani d . 1 . . C
C3 0.7825(4) 0.2152(4) 0.2769(2) 0.0458(9) Uani d . 1 . . C
C4 0.6751(4) 0.0906(4) 0.2888(2) 0.0474(9) Uani d . 1 . . C
H4A 0.7191 0.0325 0.3277 0.057 Uiso calc R 1 . . H
H4B 0.5774 0.123 0.3077 0.057 Uiso calc R 1 . . H
C5 0.6478(4) 0.0079(4) 0.2192(2) 0.0438(9) Uani d . 1 . . C
C6 0.5401(4) 0.0496(3) 0.1659(2) 0.0427(8) Uani d . 1 . . C
C7 0.4483(4) 0.2624(4) 0.12592(18) 0.0413(8) Uani d . 1 . . C
C8 0.5766(4) 0.3406(4) 0.10805(18) 0.0409(8) Uani d . 1 . . C
C9 0.7104(4) 0.3353(4) 0.23006(18) 0.0437(8) Uani d . 1 . . C
H9A 0.6043 0.3455 0.2451 0.052 Uiso calc R 1 . . H
H9B 0.7632 0.4187 0.2434 0.052 Uiso calc R 1 . . H
C10 0.8526(5) 0.3816(5) 0.1139(2) 0.0585(11) Uani d . 1 . . C
H10A 0.8637 0.352 0.062 0.088 Uiso calc R 1 . . H
H10B 0.9416 0.3559 0.1425 0.088 Uiso calc R 1 . . H
H10C 0.8415 0.4787 0.1151 0.088 Uiso calc R 1 . . H
C11 0.7241(5) -0.1121(4) 0.2053(3) 0.0616(11) Uani d . 1 . . C
H11 0.7959 -0.1426 0.2405 0.074 Uiso calc . 1 . . H
C12 0.6969(6) -0.1872(5) 0.1413(3) 0.0751(15) Uani d . 1 . . C
H12 0.751 -0.2672 0.133 0.09 Uiso calc . 1 . . H
C13 0.5892(7) -0.1447(5) 0.0888(3) 0.0717(15) Uani d . 1 . . C
H13 0.5704 -0.1962 0.0453 0.086 Uiso calc . 1 . . H
C14 0.5095(5) -0.0252(4) 0.1011(2) 0.0566(11) Uani d . 1 . . C
H14 0.4364 0.0042 0.0663 0.068 Uiso calc . 1 . . H
C15 0.3095(5) 0.2800(4) 0.0890(2) 0.0532(10) Uani d . 1 . . C
H15 0.2254 0.2275 0.1026 0.064 Uiso calc . 1 . . H
C16 0.2970(5) 0.3756(5) 0.0322(2) 0.0623(12) Uani d . 1 . . C
H16 0.2038 0.3894 0.0078 0.075 Uiso calc . 1 . . H
C17 0.4226(6) 0.4506(5) 0.0115(2) 0.0647(12) Uani d . 1 . . C
H17 0.4148 0.5126 -0.0284 0.078 Uiso calc . 1 . . H
C18 0.5611(5) 0.4353(4) 0.0492(2) 0.0516(10) Uani d . 1 . . C
H18 0.6443 0.4886 0.0352 0.062 Uiso calc . 1 . . H
N1 0.8454(6) 0.3102(5) 0.4121(2) 0.0930(15) Uani d . 1 . . N
N2 1.0350(5) 0.1192(4) 0.2179(3) 0.0802(13) Uani d . 1 . . N
N3 0.7169(3) 0.3180(3) 0.14753(15) 0.0408(7) Uani d . 1 . . N
O1 0.4574(3) 0.1658(2) 0.18347(12) 0.0428(6) Uani d . 1 . . O



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.124(5) ?
C1 C3 . 1.483(6) ?
C2 N2 . 1.146(5) ?
C2 C3 . 1.471(6) ?
C3 C4 . 1.558(5) ?
C3 C9 . 1.571(5) ?
C4 C5 . 1.486(5) ?
C5 C11 . 1.377(5) ?
C5 C6 . 1.389(5) ?
C6 C14 . 1.379(5) ?
C6 O1 . 1.387(4) ?
C7 C15 . 1.387(5) ?
C7 O1 . 1.388(4) ?
C7 C8 . 1.396(5) ?
C8 C18 . 1.397(5) ?
C8 N3 . 1.426(4) ?
C9 N3 . 1.458(4) ?
C10 N3 . 1.466(5) ?
C11 C12 . 1.365(7) ?
C12 C13 . 1.381(7) ?
C13 C14 . 1.383(6) ?
C15 C16 . 1.375(6) ?
C16 C17 . 1.372(7) ?
C17 C18 . 1.388(6) ?

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
N1 C1 C3 177.5(5) . . ?
N2 C2 C3 175.3(4) . . ?
C2 C3 C1 106.8(3) . . ?
C2 C3 C4 108.1(3) . . ?
C1 C3 C4 107.4(3) . . ?
C2 C3 C9 112.2(3) . . ?
C1 C3 C9 107.1(3) . . ?
C4 C3 C9 114.8(3) . . ?
C5 C4 C3 114.7(3) . . ?
C11 C5 C6 117.6(4) . . ?
C11 C5 C4 122.4(4) . . ?
C6 C5 C4 120.0(3) . . ?
C14 C6 O1 121.5(4) . . ?
C14 C6 C5 121.8(4) . . ?
O1 C6 C5 116.6(3) . . ?
C15 C7 O1 118.4(3) . . ?
C15 C7 C8 122.0(3) . . ?
O1 C7 C8 119.6(3) . . ?
C7 C8 C18 117.1(3) . . ?
C7 C8 N3 119.8(3) . . ?
C18 C8 N3 123.1(3) . . ?
N3 C9 C3 114.6(3) . . ?
C12 C11 C5 121.6(4) . . ?
C11 C12 C13 120.2(4) . . ?
C12 C13 C14 119.7(4) . . ?
C6 C14 C13 119.0(4) . . ?
C16 C15 C7 119.6(4) . . ?
C17 C16 C15 119.7(4) . . ?
C16 C17 C18 120.9(4) . . ?
C17 C18 C8 120.6(4) . . ?
C8 N3 C9 115.5(3) . . ?
C8 N3 C10 115.8(3) . . ?
C9 N3 C10 112.4(3) . . ?
C6 O1 C7 115.6(2) . . ?

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
