# Electronic Supplementary Material (ESI) for ChemComm.
# 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_l
_database_code_depnum_ccdc_archive 'CCDC 1450112'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-02-29 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 H10 N2 O2'
_chemical_formula_weight         250.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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                   19.7366(15)
_cell_length_b                   11.0069(8)
_cell_length_c                   14.8933(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 130.4330(10)
_cell_angle_gamma                90.00
_cell_volume                     2462.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2513
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      26.93

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7399
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         27.64
_reflns_number_total             2817
_reflns_number_gt                2075
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '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)+(0.0757P)²+0.4980P] 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         2817
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1394
_refine_ls_wR_factor_gt          0.1258
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
C1 C 0.10888(9) 0.32585(12) 0.18561(12) 0.0412(3) Uani 1 1 d . . .
N1 N 0.18684(8) 0.37981(11) 0.26628(11) 0.0479(3) Uani 1 1 d . . .
O1 O 0.26167(7) 0.32094(10) 0.32497(12) 0.0702(4) Uani 1 1 d . . .
C8 C 0.02957(9) 0.39280(12) 0.12668(11) 0.0391(3) Uani 1 1 d . . .
C3 C 0.03712(9) 0.51675(12) 0.15743(12) 0.0417(3) Uani 1 1 d . . .
N2 N 0.11913(8) 0.56941(11) 0.23950(11) 0.0506(3) Uani 1 1 d . . .
C2 C 0.18863(10) 0.50337(13) 0.28862(14) 0.0531(4) Uani 1 1 d . . .
H2B H 0.2439 0.5403 0.3427 0.064 Uiso 1 1 calc R . .
C4 C -0.03961(11) 0.58713(15) 0.10226(15) 0.0558(4) Uani 1 1 d . . .
H4A H -0.0349 0.6687 0.1218 0.067 Uiso 1 1 calc R . .
C21 C 0.11652(9) 0.10029(12) 0.23459(12) 0.0412(3) Uani 1 1 d . . .
C7 C -0.05582(10) 0.34301(14) 0.04027(13) 0.0514(4) Uani 1 1 d . . .
H7A H -0.0621 0.2620 0.0183 0.062 Uiso 1 1 calc R . .
C10 C 0.11806(11) -0.02182(13) 0.21171(16) 0.0548(4) Uani 1 1 d . . .
H10A H 0.1156 -0.0438 0.1493 0.066 Uiso 1 1 calc R . .
C9 C 0.11258(10) 0.19348(13) 0.16048(13) 0.0487(4) Uani 1 1 d . . .
C5 C -0.12109(11) 0.53608(17) 0.02002(17) 0.0641(5) Uani 1 1 d . . .
H5A H -0.1720 0.5830 -0.0160 0.077 Uiso 1 1 calc R . .
C14 C 0.11933(10) 0.13141(14) 0.32698(13) 0.0489(4) Uani 1 1 d . . .
H14A H 0.1187 0.2128 0.3432 0.059 Uiso 1 1 calc R . .
C6 C -0.12917(11) 0.41391(18) -0.01094(15) 0.0623(5) Uani 1 1 d . . .
H6A H -0.1855 0.3805 -0.0674 0.075 Uiso 1 1 calc R . .
O2 O 0.11094(12) 0.17059(11) 0.07968(13) 0.0859(5) Uani 1 1 d . . .
C12 C 0.12529(12) -0.07787(16) 0.37215(17) 0.0671(5) Uani 1 1 d . . .
H12A H 0.1281 -0.1378 0.4185 0.080 Uiso 1 1 calc R . .
C13 C 0.12313(12) 0.04199(16) 0.39509(16) 0.0622(5) Uani 1 1 d . . .
H13A H 0.1242 0.0631 0.4565 0.075 Uiso 1 1 calc R . .
C11 C 0.12331(12) -0.11027(15) 0.28183(18) 0.0666(5) Uani 1 1 d . . .
H11A H 0.1255 -0.1918 0.2676 0.080 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
C1 N1 1.3288(18) . ?
C1 C8 1.4076(18) . ?
C1 C9 1.5178(19) . ?
N1 O1 1.3003(15) . ?
N1 C2 1.3951(19) . ?
C8 C7 1.4084(19) . ?
C8 C3 1.4158(19) . ?
C3 N2 1.3725(18) . ?
C3 C4 1.398(2) . ?
N2 C2 1.282(2) . ?
C2 H2B 0.9300 . ?
C4 C5 1.359(2) . ?
C4 H4A 0.9300 . ?
C21 C14 1.384(2) . ?
C21 C10 1.392(2) . ?
C21 C9 1.471(2) . ?
C7 C6 1.362(2) . ?
C7 H7A 0.9300 . ?
C10 C11 1.382(2) . ?
C10 H10A 0.9300 . ?
C9 O2 1.2092(19) . ?
C5 C6 1.397(3) . ?
C5 H5A 0.9300 . ?
C14 C13 1.380(2) . ?
C14 H14A 0.9300 . ?
C6 H6A 0.9300 . ?
C12 C11 1.368(3) . ?
C12 C13 1.370(3) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C11 H11A 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
N1 C1 C8 119.80(12) . . ?
N1 C1 C9 116.06(12) . . ?
C8 C1 C9 124.10(13) . . ?
O1 N1 C1 121.97(12) . . ?
O1 N1 C2 118.91(12) . . ?
C1 N1 C2 119.12(12) . . ?
C1 C8 C7 123.62(13) . . ?
C1 C8 C3 117.49(12) . . ?
C7 C8 C3 118.88(12) . . ?
N2 C3 C4 119.45(13) . . ?
N2 C3 C8 120.72(12) . . ?
C4 C3 C8 119.82(13) . . ?
C2 N2 C3 118.44(13) . . ?
N2 C2 N1 124.36(13) . . ?
N2 C2 H2B 117.8 . . ?
N1 C2 H2B 117.8 . . ?
C5 C4 C3 119.88(15) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
C14 C21 C10 119.30(14) . . ?
C14 C21 C9 121.46(12) . . ?
C10 C21 C9 119.24(13) . . ?
C6 C7 C8 119.75(15) . . ?
C6 C7 H7A 120.1 . . ?
C8 C7 H7A 120.1 . . ?
C11 C10 C21 119.89(16) . . ?
C11 C10 H10A 120.1 . . ?
C21 C10 H10A 120.1 . . ?
O2 C9 C21 123.75(13) . . ?
O2 C9 C1 118.09(13) . . ?
C21 C9 C1 118.15(12) . . ?
C4 C5 C6 120.69(15) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C13 C14 C21 120.16(15) . . ?
C13 C14 H14A 119.9 . . ?
C21 C14 H14A 119.9 . . ?
C7 C6 C5 120.97(15) . . ?
C7 C6 H6A 119.5 . . ?
C5 C6 H6A 119.5 . . ?
C11 C12 C13 120.71(16) . . ?
C11 C12 H12A 119.6 . . ?
C13 C12 H12A 119.6 . . ?
C12 C13 C14 119.93(17) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C12 C11 C10 120.00(16) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        27.64
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1450113'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 N2 O3'
_chemical_formula_sum            'C15 H10 N2 O3'
_chemical_formula_weight         266.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   6.8611(4)
_cell_length_b                   18.3584(11)
_cell_length_c                   9.5657(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.0894(7)
_cell_angle_gamma                90.00
_cell_volume                     1204.88(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6452
_cell_measurement_theta_min      2.2187
_cell_measurement_theta_max      29.2257

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none

_diffrn_ambient_temperature      100(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 SMART APEX'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11488
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2760
_reflns_number_gt                2517
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0524P)²+0.5690P] 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         2760
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

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 0.4931(6) 0.5854(2) 0.4452(3) 0.0282(6) Uani 0.563(3) 1 d P A 1
O2 O 0.8152(4) 0.52809(12) 0.3297(2) 0.0241(3) Uani 0.563(3) 1 d P A 1
O3 O 0.7783(6) 0.6309(5) 0.1959(9) 0.0288(9) Uani 0.563(3) 1 d P A 1
N1 N 1.0382(4) 0.63881(14) 0.5916(3) 0.0249(3) Uani 0.563(3) 1 d P A 1
N2 N 0.8242(4) 0.57652(15) 0.4428(3) 0.0234(4) Uani 0.563(3) 1 d P A 1
C1 C 0.8724(3) 0.67006(11) 0.6531(2) 0.0199(4) Uani 0.563(3) 1 d PG A 1
C2 C 0.9034(3) 0.71795(14) 0.7634(3) 0.0290(5) Uani 0.563(3) 1 d PG A 1
H2 H 1.0323 0.7281 0.7940 0.035 Uiso 0.563(3) 1 calc PR A 1
C3 C 0.7458(4) 0.75093(14) 0.8290(3) 0.0287(3) Uani 0.563(3) 1 d PG A 1
H3 H 0.7670 0.7837 0.9045 0.034 Uiso 0.563(3) 1 calc PR A 1
C4 C 0.5571(3) 0.73602(13) 0.7842(3) 0.0272(5) Uani 0.563(3) 1 d PG A 1
H4 H 0.4494 0.7586 0.8291 0.033 Uiso 0.563(3) 1 calc PR A 1
C5 C 0.5261(3) 0.68814(12) 0.6739(2) 0.0234(4) Uani 0.563(3) 1 d PG A 1
H5 H 0.3971 0.6779 0.6433 0.028 Uiso 0.563(3) 1 calc PR A 1
C6 C 0.6837(4) 0.65515(11) 0.60829(19) 0.0200(4) Uani 0.563(3) 1 d PG A 1
C7 C 0.6494(5) 0.60338(18) 0.4931(4) 0.0216(4) Uani 0.563(3) 1 d P A 1
C8 C 1.0101(8) 0.5943(3) 0.4895(4) 0.0247(7) Uani 0.563(3) 1 d P A 1
H8 H 1.1197 0.5730 0.4447 0.030 Uiso 0.563(3) 1 calc PR A 1
C9 C 0.7855(5) 0.5654(3) 0.2010(6) 0.0218(6) Uani 0.563(3) 1 d P A 1
C10 C 0.7720(5) 0.5122(3) 0.0874(5) 0.0166(6) Uani 0.563(3) 1 d PG A 1
C11 C 0.7344(4) 0.5411(2) -0.0442(5) 0.0239(4) Uani 0.563(3) 1 d PG A 1
H11 H 0.7272 0.5924 -0.0564 0.029 Uiso 0.563(3) 1 calc PR A 1
C12 C 0.7074(4) 0.4950(2) -0.1579(4) 0.0248(6) Uani 0.563(3) 1 d PG A 1
H12 H 0.6817 0.5148 -0.2478 0.030 Uiso 0.563(3) 1 calc PR A 1
C13 C 0.7179(4) 0.4200(2) -0.1400(4) 0.0211(7) Uani 0.563(3) 1 d PG A 1
H13 H 0.6994 0.3885 -0.2177 0.025 Uiso 0.563(3) 1 calc PR A 1
C14 C 0.7555(4) 0.3911(2) -0.0084(5) 0.0273(3) Uani 0.563(3) 1 d PG A 1
H14 H 0.7626 0.3398 0.0038 0.033 Uiso 0.563(3) 1 calc PR A 1
C15 C 0.7825(4) 0.4371(3) 0.1053(4) 0.0214(7) Uani 0.563(3) 1 d PG A 1
H15 H 0.8082 0.4174 0.1952 0.026 Uiso 0.563(3) 1 calc PR A 1
O1' O 1.0010(8) 0.5847(3) 0.4449(4) 0.0282(6) Uani 0.44 1 d P A 2
O2' O 0.6788(5) 0.52780(15) 0.3304(3) 0.0241(3) Uani 0.44 1 d P A 2
O3' O 0.7163(9) 0.6303(7) 0.2023(13) 0.0288(9) Uani 0.44 1 d P A 2
N1' N 0.4581(5) 0.63763(18) 0.5929(4) 0.0249(3) Uani 0.44 1 d P A 2
N2' N 0.6713(5) 0.5752(2) 0.4427(4) 0.0234(4) Uani 0.44 1 d P A 2
C1' C 0.6236(4) 0.66936(15) 0.6533(3) 0.0199(4) Uani 0.44 1 d PG A 2
C2' C 0.5936(4) 0.71762(18) 0.7631(4) 0.0290(5) Uani 0.44 1 d PG A 2
H2' H 0.4650 0.7275 0.7945 0.035 Uiso 0.437(3) 1 calc PR A 2
C3' C 0.7516(5) 0.75138(18) 0.8270(4) 0.0287(3) Uani 0.44 1 d PG A 2
H3' H 0.7311 0.7844 0.9021 0.034 Uiso 0.437(3) 1 calc PR A 2
C4' C 0.9398(4) 0.73688(17) 0.7811(3) 0.0272(5) Uani 0.44 1 d PG A 2
H4' H 1.0478 0.7600 0.8248 0.033 Uiso 0.437(3) 1 calc PR A 2
C5' C 0.9698(4) 0.68862(16) 0.6713(3) 0.0234(4) Uani 0.44 1 d PG A 2
H5' H 1.0984 0.6787 0.6399 0.028 Uiso 0.437(3) 1 calc PR A 2
C6' C 0.8117(5) 0.65486(14) 0.6074(2) 0.0200(4) Uani 0.44 1 d PG A 2
C7' C 0.8476(6) 0.6036(2) 0.4936(5) 0.0216(4) Uani 0.44 1 d P A 2
C8' C 0.4875(11) 0.5930(4) 0.4921(6) 0.0247(7) Uani 0.44 1 d P A 2
H8' H 0.3775 0.5711 0.4488 0.030 Uiso 0.437(3) 1 calc PR A 2
C9' C 0.7098(7) 0.5659(4) 0.2050(8) 0.0218(6) Uani 0.44 1 d P A 2
C10' C 0.7262(7) 0.5153(4) 0.0851(6) 0.0166(6) Uani 0.44 1 d PG A 2
C11' C 0.7616(6) 0.5432(3) -0.0475(7) 0.0239(4) Uani 0.44 1 d PG A 2
H11' H 0.7659 0.5944 -0.0616 0.029 Uiso 0.437(3) 1 calc PR A 2
C12' C 0.7906(5) 0.4962(3) -0.1595(6) 0.0248(6) Uani 0.44 1 d PG A 2
H12' H 0.8148 0.5153 -0.2502 0.030 Uiso 0.437(3) 1 calc PR A 2
C13' C 0.7843(5) 0.4213(3) -0.1389(6) 0.0211(7) Uani 0.44 1 d PG A 2
H13' H 0.8042 0.3892 -0.2155 0.025 Uiso 0.437(3) 1 calc PR A 2
C14' C 0.7489(6) 0.3934(3) -0.0063(7) 0.0273(3) Uani 0.44 1 d PG A 2
H14' H 0.7446 0.3422 0.0078 0.033 Uiso 0.437(3) 1 calc PR A 2
C15' C 0.7199(6) 0.4403(5) 0.1057(6) 0.0214(7) Uani 0.44 1 d PG A 2
H15' H 0.6957 0.4213 0.1963 0.026 Uiso 0.437(3) 1 calc PR A 2


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 C7 1.211(5) . ?
O2 N2 1.401(4) . ?
O2 C9 1.424(6) . ?
O3 C9 1.204(10) . ?
N1 C8 1.288(5) . ?
N1 C1 1.404(3) . ?
N2 C7 1.384(5) . ?
N2 C8 1.390(6) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C2 H2 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 H4 0.9500 . ?
C5 C6 1.3900 . ?
C5 H5 0.9500 . ?
C6 C7 1.474(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.464(7) . ?
C10 C11 1.3900 . ?
C10 C15 1.3900 . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
O1' C7' 1.203(7) . ?
O2' N2' 1.383(5) . ?
O2' C9' 1.405(8) . ?
O3' C9' 1.182(14) . ?
N1' C8' 1.281(7) . ?
N1' C1' 1.400(4) . ?
N2' C8' 1.387(8) . ?
N2' C7' 1.404(6) . ?
C1' C2' 1.3900 . ?
C1' C6' 1.3900 . ?
C2' C3' 1.3900 . ?
C2' H2' 0.9500 . ?
C3' C4' 1.3900 . ?
C3' H3' 0.9500 . ?
C4' C5' 1.3900 . ?
C4' H4' 0.9500 . ?
C5' C6' 1.3900 . ?
C5' H5' 0.9500 . ?
C6' C7' 1.460(5) . ?
C8' H8' 0.9500 . ?
C9' C10' 1.481(9) . ?
C10' C11' 1.3900 . ?
C10' C15' 1.3900 . ?
C11' C12' 1.3900 . ?
C11' H11' 0.9500 . ?
C12' C13' 1.3900 . ?
C12' H12' 0.9500 . ?
C13' C14' 1.3900 . ?
C13' H13' 0.9500 . ?
C14' C15' 1.3900 . ?
C14' H14' 0.9500 . ?
C15' H15' 0.9500 . ?

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
N2 O2 C9 111.6(3) . . ?
C8 N1 C1 117.2(3) . . ?
C7 N2 C8 126.9(3) . . ?
C7 N2 O2 117.2(3) . . ?
C8 N2 O2 115.9(3) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 N1 116.97(19) . . ?
C6 C1 N1 123.03(19) . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 119.7(2) . . ?
C1 C6 C7 120.3(2) . . ?
O1 C7 N2 122.6(4) . . ?
O1 C7 C6 126.8(3) . . ?
N2 C7 C6 110.6(3) . . ?
N1 C8 N2 121.9(4) . . ?
N1 C8 H8 119.0 . . ?
N2 C8 H8 119.0 . . ?
O3 C9 O2 121.4(6) . . ?
O3 C9 C10 129.3(7) . . ?
O2 C9 C10 109.2(5) . . ?
C11 C10 C15 120.0 . . ?
C11 C10 C9 115.3(4) . . ?
C15 C10 C9 124.5(4) . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 120.0 . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
N2' O2' C9' 110.8(4) . . ?
C8' N1' C1' 116.6(5) . . ?
O2' N2' C8' 116.7(4) . . ?
O2' N2' C7' 118.0(4) . . ?
C8' N2' C7' 125.2(5) . . ?
C2' C1' C6' 120.0 . . ?
C2' C1' N1' 117.1(3) . . ?
C6' C1' N1' 122.9(3) . . ?
C3' C2' C1' 120.0 . . ?
C3' C2' H2' 120.0 . . ?
C1' C2' H2' 120.0 . . ?
C2' C3' C4' 120.0 . . ?
C2' C3' H3' 120.0 . . ?
C4' C3' H3' 120.0 . . ?
C5' C4' C3' 120.0 . . ?
C5' C4' H4' 120.0 . . ?
C3' C4' H4' 120.0 . . ?
C4' C5' C6' 120.0 . . ?
C4' C5' H5' 120.0 . . ?
C6' C5' H5' 120.0 . . ?
C5' C6' C1' 120.0 . . ?
C5' C6' C7' 118.9(3) . . ?
C1' C6' C7' 121.1(3) . . ?
O1' C7' N2' 120.8(5) . . ?
O1' C7' C6' 128.6(4) . . ?
N2' C7' C6' 110.6(4) . . ?
N1' C8' N2' 123.5(6) . . ?
N1' C8' H8' 118.2 . . ?
N2' C8' H8' 118.2 . . ?
O3' C9' O2' 121.5(8) . . ?
O3' C9' C10' 127.4(9) . . ?
O2' C9' C10' 111.1(6) . . ?
C11' C10' C15' 120.0 . . ?
C11' C10' C9' 119.3(6) . . ?
C15' C10' C9' 120.6(6) . . ?
C10' C11' C12' 120.0 . . ?
C10' C11' H11' 120.0 . . ?
C12' C11' H11' 120.0 . . ?
C13' C12' C11' 120.0 . . ?
C13' C12' H12' 120.0 . . ?
C11' C12' H12' 120.0 . . ?
C12' C13' C14' 120.0 . . ?
C12' C13' H13' 120.0 . . ?
C14' C13' H13' 120.0 . . ?
C13' C14' C15' 120.0 . . ?
C13' C14' H14' 120.0 . . ?
C15' C14' H14' 120.0 . . ?
C14' C15' C10' 120.0 . . ?
C14' C15' H15' 120.0 . . ?
C10' C15' H15' 120.0 . . ?

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
C9 O2 N2 C7 78.7(3) . . . . ?
C9 O2 N2 C8 -99.3(4) . . . . ?
C8 N1 C1 C2 179.9(3) . . . . ?
C8 N1 C1 C6 -0.2(4) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
N1 C1 C2 C3 179.9(2) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 C7 178.8(2) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
N1 C1 C6 C5 -179.9(2) . . . . ?
C2 C1 C6 C7 -178.8(2) . . . . ?
N1 C1 C6 C7 1.3(3) . . . . ?
C8 N2 C7 O1 179.3(3) . . . . ?
O2 N2 C7 O1 1.5(5) . . . . ?
C8 N2 C7 C6 -0.4(5) . . . . ?
O2 N2 C7 C6 -178.1(2) . . . . ?
C5 C6 C7 O1 0.6(4) . . . . ?
C1 C6 C7 O1 179.5(3) . . . . ?
C5 C6 C7 N2 -179.71(19) . . . . ?
C1 C6 C7 N2 -0.9(3) . . . . ?
C1 N1 C8 N2 -1.1(6) . . . . ?
C7 N2 C8 N1 1.5(6) . . . . ?
O2 N2 C8 N1 179.3(3) . . . . ?
N2 O2 C9 O3 2.9(5) . . . . ?
N2 O2 C9 C10 -178.5(3) . . . . ?
O3 C9 C10 C11 -4.1(5) . . . . ?
O2 C9 C10 C11 177.3(2) . . . . ?
O3 C9 C10 C15 179.9(4) . . . . ?
O2 C9 C10 C15 1.4(4) . . . . ?
C15 C10 C11 C12 0.0 . . . . ?
C9 C10 C11 C12 -176.2(3) . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C10 0.0 . . . . ?
C11 C10 C15 C14 0.0 . . . . ?
C9 C10 C15 C14 175.8(3) . . . . ?
C9' O2' N2' C8' 100.5(5) . . . . ?
C9' O2' N2' C7' -76.9(5) . . . . ?
C8' N1' C1' C2' -179.8(4) . . . . ?
C8' N1' C1' C6' 0.7(5) . . . . ?
C6' C1' C2' C3' 0.0 . . . . ?
N1' C1' C2' C3' -179.6(3) . . . . ?
C1' C2' C3' C4' 0.0 . . . . ?
C2' C3' C4' C5' 0.0 . . . . ?
C3' C4' C5' C6' 0.0 . . . . ?
C4' C5' C6' C1' 0.0 . . . . ?
C4' C5' C6' C7' -179.1(3) . . . . ?
C2' C1' C6' C5' 0.0 . . . . ?
N1' C1' C6' C5' 179.5(3) . . . . ?
C2' C1' C6' C7' 179.1(3) . . . . ?
N1' C1' C6' C7' -1.4(4) . . . . ?
O2' N2' C7' O1' -3.3(6) . . . . ?
C8' N2' C7' O1' 179.6(4) . . . . ?
O2' N2' C7' C6' 177.4(3) . . . . ?
C8' N2' C7' C6' 0.3(6) . . . . ?
C5' C6' C7' O1' 0.7(6) . . . . ?
C1' C6' C7' O1' -178.4(4) . . . . ?
C5' C6' C7' N2' 179.9(2) . . . . ?
C1' C6' C7' N2' 0.8(4) . . . . ?
C1' N1' C8' N2' 0.5(8) . . . . ?
O2' N2' C8' N1' -178.2(5) . . . . ?
C7' N2' C8' N1' -1.0(8) . . . . ?
N2' O2' C9' O3' -3.8(7) . . . . ?
N2' O2' C9' C10' 177.6(4) . . . . ?
O3' C9' C10' C11' 3.0(8) . . . . ?
O2' C9' C10' C11' -178.5(3) . . . . ?
O3' C9' C10' C15' 178.6(6) . . . . ?
O2' C9' C10' C15' -3.0(5) . . . . ?
C15' C10' C11' C12' 0.0 . . . . ?
C9' C10' C11' C12' 175.6(4) . . . . ?
C10' C11' C12' C13' 0.0 . . . . ?
C11' C12' C13' C14' 0.0 . . . . ?
C12' C13' C14' C15' 0.0 . . . . ?
C13' C14' C15' C10' 0.0 . . . . ?
C11' C10' C15' C14' 0.0 . . . . ?
C9' C10' C15' C14' -175.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.037
