# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1944178'
loop_
_audit_author_name
_audit_author_address
'Yunhui Hao'
;Tianjin University
China
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2021-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_audit_creation_date             2016-07-25
_chemical_formula_sum            'C15 H13 N3 O'
_chemical_formula_weight         251.280

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'


_space_group_crystal_system      Monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.8621(11)
_cell_length_b                   28.318(5)
_cell_length_c                   7.5488(15)
_cell_angle_alpha                90.000
_cell_angle_beta                 91.238(4)
_cell_angle_gamma                90.000
_cell_volume                     1252.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3459
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      27.52

_exptl_crystal_description       plate
_exptl_crystal_colour            orangered
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9828
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 5.814
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15970
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         27.52
_reflns_number_total             2886
_reflns_number_gt                2206
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_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)+(0.0883P)²+0.0037P] 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         2886
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1224
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
O1 O 0.5771(1) 0.1574(0) 0.4966(1) 1.000 4 e ? d Uani 0.02138(19)
N1 N -0.6972(2) -0.1898(0) -0.0414(1) 1.000 4 e ? d Uani 0.0312(2)
N2 N 0.0360(1) -0.0212(0) 0.2625(1) 1.000 4 e ? d Uani 0.0175(2)
N3 N -0.0276(1) 0.0211(0) 0.2412(1) 1.000 4 e ? d Uani 0.0172(2)
C1 C -0.1255(2) -0.0550(0) 0.1970(1) 1.000 4 e ? d Uani 0.0158(2)
C2 C -0.0612(2) -0.1022(0) 0.2129(1) 1.000 4 e ? d Uani 0.0182(2)
H2 H 0.0824 -0.1101 0.2656 1.000 4 e ? calc Uiso 0.02200
C3 C -0.2065(2) -0.1375(0) 0.1520(1) 1.000 4 e ? d Uani 0.0197(2)
H3 H -0.1626 -0.1697 0.1619 1.000 4 e ? calc Uiso 0.02400
C4 C -0.4182(2) -0.1254(0) 0.0757(1) 1.000 4 e ? d Uani 0.0180(2)
C5 C -0.4840(2) -0.0780(0) 0.0608(1) 1.000 4 e ? d Uani 0.0185(2)
H5 H -0.6280 -0.0700 0.0092 1.000 4 e ? calc Uiso 0.02200
C6 C -0.3381(2) -0.0431(0) 0.1216(1) 1.000 4 e ? d Uani 0.0177(2)
H6 H -0.3821 -0.0109 0.1124 1.000 4 e ? calc Uiso 0.02100
C7 C -0.5721(2) -0.1616(0) 0.0108(1) 1.000 4 e ? d Uani 0.0222(2)
C8 C 0.1312(2) 0.0550(0) 0.3060(1) 1.000 4 e ? d Uani 0.0157(2)
C9 C 0.0651(2) 0.1020(0) 0.2957(1) 1.000 4 e ? d Uani 0.0177(2)
H9 H -0.0802 0.1099 0.2458 1.000 4 e ? calc Uiso 0.02100
C10 C 0.2087(2) 0.1378(0) 0.3573(1) 1.000 4 e ? d Uani 0.0187(2)
H10 H 0.1621 0.1699 0.3500 1.000 4 e ? calc Uiso 0.02200
C11 C 0.4224(2) 0.1260(0) 0.4302(1) 1.000 4 e ? d Uani 0.0163(2)
C12 C 0.4909(2) 0.0785(0) 0.4393(1) 1.000 4 e ? d Uani 0.0170(2)
H12 H 0.6366 0.0705 0.4881 1.000 4 e ? calc Uiso 0.02000
C13 C 0.3473(2) 0.0435(0) 0.3777(1) 1.000 4 e ? d Uani 0.0165(2)
H13 H 0.3943 0.0115 0.3836 1.000 4 e ? calc Uiso 0.02000
C14 C 0.5160(2) 0.2067(0) 0.4931(1) 1.000 4 e ? d Uani 0.0236(2)
H14A H 0.3791 0.2122 0.5647 1.000 4 e ? calc Uiso 0.02800
H14B H 0.4823 0.2170 0.3700 1.000 4 e ? calc Uiso 0.02800
C15 C 0.7160(2) 0.2336(0) 0.5690(2) 1.000 4 e ? d Uani 0.0340(3)
H15A H 0.7566 0.2211 0.6865 1.000 4 e ? calc Uiso 0.05100
H15B H 0.6756 0.2671 0.5792 1.000 4 e ? calc Uiso 0.05100
H15C H 0.8463 0.2303 0.4908 1.000 4 e ? calc Uiso 0.05100



_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_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 . . 1.3582(10) no
O1 C14 . . 1.4414(12) no
N1 C7 . . 1.1482(13) no
N2 N3 . . 1.2638(12) no
N2 C1 . . 1.4270(12) no
N3 C8 . . 1.4175(12) no
C1 C2 . . 1.3932(13) no
C1 C6 . . 1.3998(13) no
C2 C3 . . 1.3861(13) no
C2 H2 . . 0.9500 no
C3 C4 . . 1.3996(14) no
C3 H3 . . 0.9500 no
C4 C5 . . 1.4003(13) no
C4 C7 . . 1.4442(11) no
C5 C6 . . 1.3796(13) no
C5 H5 . . 0.9500 no
C6 H6 . . 0.9500 no
C8 C9 . . 1.3879(13) no
C8 C13 . . 1.4044(13) no
C9 C10 . . 1.3913(11) no
C9 H9 . . 0.9500 no
C10 C11 . . 1.3976(13) no
C10 H10 . . 0.9500 no
C11 C12 . . 1.4045(13) no
C12 C13 . . 1.3743(13) no
C12 H12 . . 0.9500 no
C13 H13 . . 0.9500 no
C14 C15 . . 1.5017(14) no
C14 H14A . . 0.9900 no
C14 H14B . . 0.9900 no
C15 H15A . . 0.9800 no
C15 H15B . . 0.9800 no
C15 H15C . . 0.9800 no
C15 H15C . . 0.9800 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O1 C14 . . . 117.68(7) no
N3 N2 C1 . . . 113.59(8) no
N2 N3 C8 . . . 114.14(8) no
C2 C1 C6 . . . 120.15(9) no
C2 C1 N2 . . . 115.95(8) no
C6 C1 N2 . . . 123.88(3) no
C3 C2 C1 . . . 120.05(9) no
C3 C2 H2 . . . 120.00 no
C1 C2 H2 . . . 120.00 no
C2 C3 C4 . . . 119.56(4) no
C2 C3 H3 . . . 120.20 no
C4 C3 H3 . . . 120.20 no
C3 C4 C5 . . . 120.50(9) no
C3 C4 C7 . . . 120.51(4) no
C5 C4 C7 . . . 118.92(9) no
C6 C5 C4 . . . 119.52(9) no
C6 C5 H5 . . . 120.20 no
C4 C5 H5 . . . 120.20 no
C5 C6 C1 . . . 120.20(4) no
C5 C6 H6 . . . 119.90 no
C1 C6 H6 . . . 119.90 no
N1 C7 C4 . . . 178.88(11) no
C9 C8 C13 . . . 119.44(9) no
C9 C8 N3 . . . 116.78(8) no
C13 C8 N3 . . . 123.79(3) no
C8 C9 C10 . . . 120.87(9) no
C8 C9 H9 . . . 119.60 no
C10 C9 H9 . . . 119.60 no
C9 C10 C11 . . . 119.21(4) no
C9 C10 H10 . . . 120.40 no
C11 C10 H10 . . . 120.40 no
O1 C11 C10 . . . 125.05(3) no
O1 C11 C12 . . . 114.94(8) no
C10 C11 C12 . . . 120.08(8) no
C13 C12 C11 . . . 120.04(8) no
C13 C12 H12 . . . 120.00 no
C11 C12 H12 . . . 120.00 no
C12 C13 C8 . . . 120.24(4) no
C12 C13 H13 . . . 119.80 no
C8 C13 H13 . . . 119.80 no
O1 C14 C15 . . . 107.07(8) no
O1 C14 H14A . . . 110.30 no
C15 C14 H14A . . . 110.30 no
O1 C14 H14B . . . 110.30 no
C15 C14 H14B . . . 110.30 no
H14A C14 H14B . . . 108.60 no
C14 C15 H15A . . . 109.50 no
C14 C15 H15B . . . 109.50 no
H15A C15 H15B . . . 109.50 no
C14 C15 H15C . . . 109.50 no
H15A C15 H15C . . . 109.50 no
H15B C15 H15C . . . 109.50 no

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N2 N3 C8 . . . . 179.91(7) no
N3 N2 C1 C2 . . . . 178.38(8) no
N3 N2 C1 C6 . . . . -2.13(14) no
C6 C1 C2 C3 . . . . 0.87(15) no
N2 C1 C2 C3 . . . . -179.61(8) no
C1 C2 C3 C4 . . . . -0.47(15) no
C2 C3 C4 C5 . . . . -0.02(15) no
C2 C3 C4 C7 . . . . 179.80(9) no
C3 C4 C5 C6 . . . . 0.11(15) no
C7 C4 C5 C6 . . . . -179.71(9) no
C4 C5 C6 C1 . . . . 0.29(14) no
C2 C1 C6 C5 . . . . -0.79(14) no
N2 C1 C6 C5 . . . . 179.74(8) no
C3 C4 C7 N1 . . . . 173.(100) no
C5 C4 C7 N1 . . . . -8.(6) no
N2 N3 C8 C9 . . . . -176.38(8) no
N2 N3 C8 C13 . . . . 3.90(14) no
C13 C8 C9 C10 . . . . -0.83(15) no
N3 C8 C9 C10 . . . . 179.44(8) no
C8 C9 C10 C11 . . . . 0.13(15) no
C14 O1 C11 C10 . . . . 0.49(14) no
C14 O1 C11 C12 . . . . -179.30(8) no
C9 C10 C11 O1 . . . . -179.27(8) no
C9 C10 C11 C12 . . . . 0.51(14) no
O1 C11 C12 C13 . . . . 179.35(8) no
C10 C11 C12 C13 . . . . -0.45(14) no
C11 C12 C13 C8 . . . . -0.25(14) no
C9 C8 C13 C12 . . . . 0.89(14) no
N3 C8 C13 C12 . . . . -179.40(8) no
C11 O1 C14 C15 . . . . -178.64(8) no

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_m20160629e1
_database_code_depnum_ccdc_archive 'CCDC 1944179'
loop_
_audit_author_name
_audit_author_address
'Yunhui Hao'
;Tianjin University
China
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2021-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 N3 O'
_chemical_formula_weight         251.28

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   P2(1)/n

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

_cell_length_a                   4.6333(11)
_cell_length_b                   24.671(6)
_cell_length_c                   10.843(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.761(9)
_cell_angle_gamma                90.00
_cell_volume                     1235.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3459
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            orangered
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9826
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 5.814
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11951
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         27.54
_reflns_number_total             2776
_reflns_number_gt                2206
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'

_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)+(0.0883P)²+0.0037P] 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         2776
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 -0.42424(16) 0.37201(3) 0.52291(7) 0.0234(2) Uani 1 1 d . . .
N1 N 1.5207(2) -0.00614(4) 0.67328(9) 0.0313(3) Uani 1 1 d . . .
N2 N 0.50124(19) 0.18899(4) 0.54953(8) 0.0216(2) Uani 1 1 d . . .
N3 N 0.40507(19) 0.21294(3) 0.64027(8) 0.0215(2) Uani 1 1 d . . .
C1 C 1.3516(2) 0.02731(4) 0.65059(10) 0.0238(3) Uani 1 1 d . . .
C2 C 1.1365(2) 0.06911(4) 0.62620(10) 0.0215(2) Uani 1 1 d . . .
C3 C 1.0285(2) 0.08070(5) 0.50506(10) 0.0241(3) Uani 1 1 d . . .
H3 H 1.0976 0.0615 0.4375 0.029 Uiso 1 1 calc R . .
C4 C 0.8190(2) 0.12055(4) 0.48462(10) 0.0239(3) Uani 1 1 d . . .
H4 H 0.7439 0.1286 0.4025 0.029 Uiso 1 1 calc R . .
C5 C 0.7174(2) 0.14895(4) 0.58328(10) 0.0206(2) Uani 1 1 d . . .
C6 C 0.8280(2) 0.13746(4) 0.70471(10) 0.0224(2) Uani 1 1 d . . .
H6 H 0.7604 0.1570 0.7721 0.027 Uiso 1 1 calc R . .
C7 C 1.0358(2) 0.09762(4) 0.72591(10) 0.0225(2) Uani 1 1 d . . .
H7 H 1.1104 0.0895 0.8081 0.027 Uiso 1 1 calc R . .
C8 C 0.1914(2) 0.25274(4) 0.60659(10) 0.0199(2) Uani 1 1 d . . .
C9 C 0.0918(2) 0.26552(4) 0.48385(10) 0.0214(2) Uani 1 1 d . . .
H9 H 0.1670 0.2468 0.4169 0.026 Uiso 1 1 calc R . .
C10 C -0.1141(2) 0.30505(4) 0.46105(10) 0.0215(2) Uani 1 1 d . . .
H10 H -0.1815 0.3134 0.3781 0.026 Uiso 1 1 calc R . .
C11 C -0.2263(2) 0.33317(4) 0.55867(10) 0.0198(2) Uani 1 1 d . . .
C12 C -0.1318(2) 0.32052(4) 0.68083(10) 0.0219(2) Uani 1 1 d . . .
H12 H -0.2084 0.3391 0.7476 0.026 Uiso 1 1 calc R . .
C13 C 0.0761(2) 0.28027(4) 0.70335(10) 0.0222(3) Uani 1 1 d . . .
H13 H 0.1408 0.2714 0.7863 0.027 Uiso 1 1 calc R . .
C14 C -0.5330(2) 0.40710(4) 0.61438(10) 0.0253(3) Uani 1 1 d . . .
H14A H -0.3733 0.4284 0.6569 0.030 Uiso 1 1 calc R . .
H14B H -0.6271 0.3856 0.6769 0.030 Uiso 1 1 calc R . .
C15 C -0.7494(3) 0.44412(5) 0.54591(12) 0.0292(3) Uani 1 1 d . . .
H15A H -0.6534 0.4649 0.4840 0.044 Uiso 1 1 calc R . .
H15B H -0.8294 0.4691 0.6046 0.044 Uiso 1 1 calc R . .
H15C H -0.9063 0.4225 0.5045 0.044 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 1.3603(12) . ?
O1 C14 1.4387(13) . ?
N1 C1 1.1503(14) . ?
N2 N3 1.2604(13) . ?
N2 C5 1.4324(14) . ?
N3 C8 1.4202(14) . ?
C1 C2 1.4434(15) . ?
C2 C3 1.3958(16) . ?
C2 C7 1.4018(15) . ?
C3 C4 1.3864(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3930(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.4016(15) . ?
C6 C7 1.3815(15) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.3930(15) . ?
C8 C9 1.4077(15) . ?
C9 C10 1.3725(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.4012(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.3954(15) . ?
C12 C13 1.3910(15) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.5056(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
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
C11 O1 C14 119.59(8) . . ?
N3 N2 C5 114.13(9) . . ?
N2 N3 C8 114.05(9) . . ?
N1 C1 C2 178.11(11) . . ?
C3 C2 C7 120.43(10) . . ?
C3 C2 C1 120.47(10) . . ?
C7 C2 C1 119.10(10) . . ?
C4 C3 C2 119.16(10) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.71(10) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 119.94(10) . . ?
C4 C5 N2 115.11(9) . . ?
C6 C5 N2 124.95(9) . . ?
C7 C6 C5 119.71(10) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C2 120.04(10) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C13 C8 C9 119.12(10) . . ?
C13 C8 N3 116.49(9) . . ?
C9 C8 N3 124.39(10) . . ?
C10 C9 C8 119.87(10) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.78(10) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
O1 C11 C12 125.39(9) . . ?
O1 C11 C10 114.65(9) . . ?
C12 C11 C10 119.96(10) . . ?
C13 C12 C11 118.98(10) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C8 121.28(9) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
O1 C14 C15 106.38(9) . . ?
O1 C14 H14A 110.5 . . ?
C15 C14 H14A 110.5 . . ?
O1 C14 H14B 110.5 . . ?
C15 C14 H14B 110.5 . . ?
H14A C14 H14B 108.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
C5 N2 N3 C8 179.81(8) . . . . ?
N1 C1 C2 C3 -157(3) . . . . ?
N1 C1 C2 C7 23(4) . . . . ?
C7 C2 C3 C4 -0.38(16) . . . . ?
C1 C2 C3 C4 179.10(9) . . . . ?
C2 C3 C4 C5 0.23(16) . . . . ?
C3 C4 C5 C6 0.23(16) . . . . ?
C3 C4 C5 N2 -179.97(9) . . . . ?
N3 N2 C5 C4 177.71(9) . . . . ?
N3 N2 C5 C6 -2.50(15) . . . . ?
C4 C5 C6 C7 -0.53(16) . . . . ?
N2 C5 C6 C7 179.69(9) . . . . ?
C5 C6 C7 C2 0.38(16) . . . . ?
C3 C2 C7 C6 0.07(16) . . . . ?
C1 C2 C7 C6 -179.41(9) . . . . ?
N2 N3 C8 C13 179.61(9) . . . . ?
N2 N3 C8 C9 -0.28(15) . . . . ?
C13 C8 C9 C10 0.65(15) . . . . ?
N3 C8 C9 C10 -179.47(9) . . . . ?
C8 C9 C10 C11 0.29(16) . . . . ?
C14 O1 C11 C12 5.73(15) . . . . ?
C14 O1 C11 C10 -173.92(9) . . . . ?
C9 C10 C11 O1 178.68(9) . . . . ?
C9 C10 C11 C12 -0.99(16) . . . . ?
O1 C11 C12 C13 -178.91(9) . . . . ?
C10 C11 C12 C13 0.73(15) . . . . ?
C11 C12 C13 C8 0.22(16) . . . . ?
C9 C8 C13 C12 -0.91(15) . . . . ?
N3 C8 C13 C12 179.20(9) . . . . ?
C11 O1 C14 C15 -178.86(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.048
