# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1507744'
_audit_update_record             
;
2016-10-02 deposited with the CCDC.
2017-05-29 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H16 N4 O4'
_chemical_formula_weight         448.43

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                   5.588(3)
_cell_length_b                   7.545(4)
_cell_length_c                   11.984(6)
_cell_angle_alpha                77.113(11)
_cell_angle_beta                 88.392(13)
_cell_angle_gamma                87.412(12)
_cell_volume                     492.0(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4765
_cell_measurement_theta_min      3.3429
_cell_measurement_theta_max      62.6698

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             232
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.29101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  Oxford
_diffrn_measurement_method       'ω and π scan'
_diffrn_detector_area_resol_mean 16.0855
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            4205
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0707
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.49
_diffrn_reflns_theta_max         25.99
_reflns_number_total             1916
_reflns_number_gt                1232
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0520P)²+0.0000P] 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         1916
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
C9 C 0.4786(3) 0.9432(2) 0.96175(11) 0.0338(4) Uani 1 1 d . . .
C8 C 0.2825(3) 0.9862(2) 0.88685(12) 0.0356(4) Uani 1 1 d . . .
C10 C 0.6319(3) 0.7893(2) 0.96211(12) 0.0361(4) Uani 1 1 d . . .
C11 C 0.5897(3) 0.6698(3) 0.88203(13) 0.0406(4) Uani 1 1 d . . .
C13 C 0.8216(3) 0.7503(3) 1.03621(13) 0.0407(4) Uani 1 1 d . . .
H13A H 0.9223 0.6488 1.0359 0.049 Uiso 1 1 calc R . .
C7 C 0.2329(3) 0.8647(3) 0.80935(12) 0.0380(4) Uani 1 1 d . . .
C12 C 0.1368(3) 1.1378(3) 0.88830(13) 0.0405(4) Uani 1 1 d . . .
H12A H 0.0090 1.1661 0.8385 0.049 Uiso 1 1 calc R . .
C6 C 0.3400(3) 0.5969(3) 0.73270(14) 0.0453(5) Uani 1 1 d . . .
H6A H 0.1703 0.5738 0.7375 0.054 Uiso 1 1 calc R . .
H6B H 0.4269 0.4811 0.7573 0.054 Uiso 1 1 calc R . .
C5 C 0.4081(3) 0.6785(3) 0.60947(13) 0.0406(4) Uani 1 1 d . . .
C1 C 0.6216(3) 0.7655(3) 0.57813(14) 0.0476(5) Uani 1 1 d . . .
H1A H 0.7279 0.7794 0.6336 0.057 Uiso 1 1 calc R . .
C4 C 0.2595(3) 0.6639(3) 0.52181(15) 0.0515(5) Uani 1 1 d . . .
H4A H 0.1143 0.6072 0.5382 0.062 Uiso 1 1 calc R . .
C2 C 0.6736(4) 0.8310(3) 0.46359(16) 0.0549(5) Uani 1 1 d . . .
H2A H 0.8170 0.8893 0.4444 0.066 Uiso 1 1 calc R . .
C3 C 0.3289(4) 0.7343(3) 0.40959(16) 0.0625(6) Uani 1 1 d . . .
H3A H 0.2258 0.7231 0.3522 0.075 Uiso 1 1 calc R . .
O1 O 0.0602(2) 0.88923(19) 0.74719(9) 0.0499(4) Uani 1 1 d . . .
O2 O 0.7183(2) 0.5365(2) 0.87774(11) 0.0568(4) Uani 1 1 d . . .
N2 N 0.3918(2) 0.7155(2) 0.81097(10) 0.0396(4) Uani 1 1 d . . .
N1 N 0.5320(3) 0.8165(3) 0.37839(13) 0.0632(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C9 0.0371(9) 0.0381(11) 0.0255(8) -0.0059(6) 0.0021(6) -0.0020(7)
C8 0.0369(8) 0.0413(11) 0.0278(7) -0.0065(6) 0.0017(6) -0.0016(7)
C10 0.0402(9) 0.0377(11) 0.0301(7) -0.0070(6) 0.0021(6) -0.0010(7)
C11 0.0467(10) 0.0404(11) 0.0341(8) -0.0080(7) 0.0009(7) 0.0006(8)
C13 0.0426(9) 0.0430(11) 0.0358(8) -0.0086(7) 0.0000(6) 0.0058(8)
C7 0.0402(9) 0.0456(11) 0.0282(7) -0.0079(6) 0.0001(6) -0.0040(7)
C12 0.0392(9) 0.0491(12) 0.0325(8) -0.0080(7) -0.0053(6) 0.0030(8)
C6 0.0554(11) 0.0431(12) 0.0414(9) -0.0172(7) -0.0011(7) -0.0061(8)
C5 0.0461(9) 0.0405(11) 0.0391(9) -0.0180(7) -0.0029(7) 0.0040(8)
C1 0.0477(10) 0.0539(13) 0.0426(9) -0.0133(8) -0.0057(7) -0.0002(9)
C4 0.0489(11) 0.0620(14) 0.0499(10) -0.0256(9) -0.0058(8) 0.0004(9)
C2 0.0555(11) 0.0576(14) 0.0496(10) -0.0094(9) 0.0059(8) 0.0019(9)
C3 0.0689(13) 0.0811(18) 0.0429(10) -0.0260(9) -0.0153(9) 0.0099(12)
O1 0.0470(7) 0.0635(10) 0.0426(7) -0.0179(6) -0.0084(5) -0.0020(6)
O2 0.0644(9) 0.0509(10) 0.0599(8) -0.0245(6) -0.0097(6) 0.0141(7)
N2 0.0494(8) 0.0402(9) 0.0318(7) -0.0134(6) -0.0013(6) -0.0023(7)
N1 0.0705(12) 0.0757(15) 0.0425(9) -0.0141(8) 0.0004(7) 0.0104(10)

_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
C9 C9 1.419(3) 2_677 ?
C9 C8 1.416(2) . ?
C9 C10 1.411(2) . ?
C8 C12 1.377(3) . ?
C8 C7 1.482(3) . ?
C10 C13 1.381(2) . ?
C10 C11 1.485(3) . ?
C11 O2 1.219(2) . ?
C11 N2 1.398(2) . ?
C13 C12 1.399(3) 2_677 ?
C13 H13A 0.9300 . ?
C7 O1 1.2177(19) . ?
C7 N2 1.399(2) . ?
C12 C13 1.399(3) 2_677 ?
C12 H12A 0.9300 . ?
C6 N2 1.476(2) . ?
C6 C5 1.513(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 C4 1.383(2) . ?
C5 C1 1.390(3) . ?
C1 C2 1.379(3) . ?
C1 H1A 0.9300 . ?
C4 C3 1.383(3) . ?
C4 H4A 0.9300 . ?
C2 N1 1.335(3) . ?
C2 H2A 0.9300 . ?
C3 N1 1.323(3) . ?
C3 H3A 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
C9 C9 C8 119.39(19) 2_677 . ?
C9 C9 C10 119.31(17) 2_677 . ?
C8 C9 C10 121.30(16) . . ?
C12 C8 C9 119.88(17) . . ?
C12 C8 C7 120.62(15) . . ?
C9 C8 C7 119.49(16) . . ?
C13 C10 C9 120.12(17) . . ?
C13 C10 C11 120.05(16) . . ?
C9 C10 C11 119.82(15) . . ?
O2 C11 N2 120.48(18) . . ?
O2 C11 C10 122.55(16) . . ?
N2 C11 C10 116.97(16) . . ?
C10 C13 C12 120.47(17) . 2_677 ?
C10 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 2_677 . ?
O1 C7 N2 120.12(17) . . ?
O1 C7 C8 122.58(17) . . ?
N2 C7 C8 117.30(14) . . ?
C8 C12 C13 120.83(15) . 2_677 ?
C8 C12 H12A 119.6 . . ?
C13 C12 H12A 119.6 2_677 . ?
N2 C6 C5 112.90(15) . . ?
N2 C6 H6A 109.0 . . ?
C5 C6 H6A 109.0 . . ?
N2 C6 H6B 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C4 C5 C1 116.91(16) . . ?
C4 C5 C6 120.36(17) . . ?
C1 C5 C6 122.70(15) . . ?
C2 C1 C5 119.06(17) . . ?
C2 C1 H1A 120.5 . . ?
C5 C1 H1A 120.5 . . ?
C5 C4 C3 119.40(19) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
N1 C2 C1 124.45(19) . . ?
N1 C2 H2A 117.8 . . ?
C1 C2 H2A 117.8 . . ?
N1 C3 C4 124.41(19) . . ?
N1 C3 H3A 117.8 . . ?
C4 C3 H3A 117.8 . . ?
C7 N2 C11 125.06(16) . . ?
C7 N2 C6 116.43(14) . . ?
C11 N2 C6 118.50(16) . . ?
C3 N1 C2 115.78(17) . . ?

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 C9 C8 C12 0.5(2) 2_677 . . . ?
C10 C9 C8 C12 -179.75(13) . . . . ?
C9 C9 C8 C7 -178.14(15) 2_677 . . . ?
C10 C9 C8 C7 1.6(2) . . . . ?
C9 C9 C10 C13 -0.1(2) 2_677 . . . ?
C8 C9 C10 C13 -179.85(14) . . . . ?
C9 C9 C10 C11 -179.71(16) 2_677 . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C13 C10 C11 O2 -0.6(2) . . . . ?
C9 C10 C11 O2 179.07(15) . . . . ?
C13 C10 C11 N2 178.84(13) . . . . ?
C9 C10 C11 N2 -1.5(2) . . . . ?
C9 C10 C13 C12 0.2(2) . . . 2_677 ?
C11 C10 C13 C12 179.82(14) . . . 2_677 ?
C12 C8 C7 O1 -2.4(2) . . . . ?
C9 C8 C7 O1 176.22(14) . . . . ?
C12 C8 C7 N2 178.67(12) . . . . ?
C9 C8 C7 N2 -2.7(2) . . . . ?
C9 C8 C12 C13 -0.6(2) . . . 2_677 ?
C7 C8 C12 C13 178.00(14) . . . 2_677 ?
N2 C6 C5 C4 -138.81(19) . . . . ?
N2 C6 C5 C1 43.2(2) . . . . ?
C4 C5 C1 C2 -0.2(3) . . . . ?
C6 C5 C1 C2 177.92(19) . . . . ?
C1 C5 C4 C3 0.2(3) . . . . ?
C6 C5 C4 C3 -177.93(19) . . . . ?
C5 C1 C2 N1 -0.3(3) . . . . ?
C5 C4 C3 N1 0.2(4) . . . . ?
O1 C7 N2 C11 -177.23(14) . . . . ?
C8 C7 N2 C11 1.7(2) . . . . ?
O1 C7 N2 C6 1.4(2) . . . . ?
C8 C7 N2 C6 -179.67(13) . . . . ?
O2 C11 N2 C7 179.76(14) . . . . ?
C10 C11 N2 C7 0.3(2) . . . . ?
O2 C11 N2 C6 1.2(2) . . . . ?
C10 C11 N2 C6 -178.21(13) . . . . ?
C5 C6 N2 C7 76.49(18) . . . . ?
C5 C6 N2 C11 -104.83(18) . . . . ?
C4 C3 N1 C2 -0.6(3) . . . . ?
C1 C2 N1 C3 0.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.049

#============================================END 
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1507742'
_audit_update_record             
;
2016-10-02 deposited with the CCDC.
2017-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H16 N4 O6'
_chemical_formula_weight         480.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   27.561(3)
_cell_length_b                   4.6812(2)
_cell_length_c                   21.646(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 128.914(17)
_cell_angle_gamma                90.00
_cell_volume                     2173.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5133
_cell_measurement_theta_min      3.5429
_cell_measurement_theta_max      62.3698

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.29101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Oxford
_diffrn_measurement_method       'ω and π scan'
_diffrn_detector_area_resol_mean 16.0855
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            4658
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.12
_diffrn_reflns_theta_max         59.97
_reflns_number_total             1611
_reflns_number_gt                1502
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0671P)²+1.2017P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    geom
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1611
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.17330(5) 0.4718(2) 0.04889(6) 0.0362(3) Uani 1 1 d . . .
O2 O 0.01859(5) 1.0760(3) -0.13255(7) 0.0430(3) Uani 1 1 d . . .
N2 N 0.09631(5) 0.7783(3) -0.04017(7) 0.0300(3) Uani 1 1 d . . .
C9 C 0.01910(7) 0.5546(3) -0.00865(8) 0.0261(4) Uani 1 1 d . . .
C8 C 0.08085(7) 0.4519(3) 0.03510(8) 0.0279(4) Uani 1 1 d . . .
C10 C -0.00501(7) 0.7629(3) -0.06846(8) 0.0283(4) Uani 1 1 d . . .
C7 C 0.12116(7) 0.5623(3) 0.01687(9) 0.0292(4) Uani 1 1 d . . .
C6 C 0.13812(7) 0.9068(3) -0.05312(10) 0.0339(4) Uani 1 1 d . . .
H6A H 0.1797 0.9204 -0.0024 0.041 Uiso 1 1 calc R . .
H6B H 0.1239 1.0995 -0.0730 0.041 Uiso 1 1 calc R . .
C13 C -0.06552(7) 0.8576(3) -0.11042(9) 0.0319(4) Uani 1 1 d . . .
H13A H -0.0811 0.9943 -0.1500 0.038 Uiso 1 1 calc R . .
C11 C 0.03579(7) 0.8868(3) -0.08439(9) 0.0314(4) Uani 1 1 d . . .
C12 C 0.10374(7) 0.2508(3) 0.09387(8) 0.0311(4) Uani 1 1 d . . .
H12A H 0.1446 0.1867 0.1227 0.037 Uiso 1 1 calc R . .
C1 C 0.19231(7) 0.7959(4) -0.10869(10) 0.0381(4) Uani 1 1 d . . .
H1A H 0.2231 0.9254 -0.0727 0.046 Uiso 1 1 calc R . .
N1 N 0.15410(6) 0.4633(3) -0.21412(8) 0.0407(4) Uani 1 1 d . . .
C5 C 0.14207(7) 0.7454(3) -0.11007(9) 0.0300(4) Uani 1 1 d . . .
C4 C 0.09735(7) 0.5556(3) -0.16609(9) 0.0356(4) Uani 1 1 d . . .
H4A H 0.0622 0.5189 -0.1703 0.043 Uiso 1 1 calc R . .
C3 C 0.10534(8) 0.4202(4) -0.21604(10) 0.0415(4) Uani 1 1 d . . .
H3A H 0.0749 0.2916 -0.2531 0.050 Uiso 1 1 calc R . .
C2 C 0.19629(7) 0.6531(4) -0.16093(10) 0.0402(4) Uani 1 1 d . . .
H2A H 0.2303 0.6909 -0.1591 0.048 Uiso 1 1 calc R . .
O1W O 0.21293(6) 0.2371(3) -0.27702(8) 0.0484(4) Uani 1 1 d . . .
H1B H 0.1915(12) 0.282(6) -0.2563(15) 0.087(8) Uiso 1 1 d . . .
H1C H 0.2415(15) 0.061(7) -0.2435(19) 0.113(10) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0270(6) 0.0447(7) 0.0456(6) -0.0026(5) 0.0270(5) -0.0008(5)
O2 0.0419(7) 0.0498(7) 0.0481(7) 0.0142(6) 0.0336(6) 0.0035(5)
N2 0.0308(7) 0.0339(7) 0.0384(7) -0.0039(5) 0.0280(6) -0.0041(5)
C9 0.0272(7) 0.0283(8) 0.0298(7) -0.0063(6) 0.0213(6) -0.0032(6)
C8 0.0266(7) 0.0315(8) 0.0319(8) -0.0068(6) 0.0214(6) -0.0030(6)
C10 0.0303(8) 0.0319(8) 0.0310(7) -0.0043(6) 0.0232(7) -0.0027(6)
C7 0.0286(8) 0.0327(8) 0.0339(8) -0.0083(6) 0.0233(7) -0.0051(6)
C6 0.0346(8) 0.0355(8) 0.0454(9) -0.0045(7) 0.0318(8) -0.0067(7)
C13 0.0321(8) 0.0365(8) 0.0319(8) 0.0004(6) 0.0225(7) 0.0006(6)
C11 0.0333(8) 0.0352(9) 0.0347(8) -0.0039(7) 0.0257(7) -0.0027(6)
C12 0.0251(7) 0.0378(8) 0.0330(8) -0.0011(6) 0.0196(6) 0.0015(6)
C1 0.0348(8) 0.0470(10) 0.0433(9) -0.0048(7) 0.0296(8) -0.0073(7)
N1 0.0410(8) 0.0520(9) 0.0396(7) 0.0004(6) 0.0304(7) 0.0025(6)
C5 0.0310(8) 0.0317(8) 0.0353(8) 0.0039(6) 0.0247(7) 0.0006(6)
C4 0.0315(8) 0.0432(9) 0.0417(9) -0.0023(7) 0.0276(7) -0.0041(6)
C3 0.0390(9) 0.0508(10) 0.0393(9) -0.0094(7) 0.0268(8) -0.0081(7)
C2 0.0354(8) 0.0545(10) 0.0447(9) -0.0007(8) 0.0318(8) -0.0024(8)
O1W 0.0544(8) 0.0521(8) 0.0603(8) -0.0036(6) 0.0463(7) 0.0004(6)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2141(18) . ?
O2 C11 1.2146(19) . ?
N2 C11 1.397(2) . ?
N2 C7 1.398(2) . ?
N2 C6 1.4747(18) . ?
C9 C8 1.414(2) . ?
C9 C9 1.416(3) 5_565 ?
C9 C10 1.410(2) . ?
C8 C12 1.376(2) . ?
C8 C7 1.486(2) . ?
C10 C13 1.378(2) . ?
C10 C11 1.485(2) . ?
C6 C5 1.507(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C13 C12 1.403(2) 5_565 ?
C13 H13A 0.9300 . ?
C12 C13 1.403(2) 5_565 ?
C12 H12A 0.9300 . ?
C1 C5 1.387(2) . ?
C1 C2 1.376(2) . ?
C1 H1A 0.9300 . ?
N1 C3 1.334(2) . ?
N1 C2 1.336(2) . ?
C5 C4 1.379(2) . ?
C4 C3 1.385(2) . ?
C4 H4A 0.9300 . ?
C3 H3A 0.9300 . ?
C2 H2A 0.9300 . ?
O1W H1B 0.96(3) . ?
O1W H1C 1.05(3) . ?

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 N2 C7 125.46(12) . . ?
C11 N2 C6 117.44(13) . . ?
C7 N2 C6 117.08(12) . . ?
C8 C9 C9 118.81(17) . 5_565 ?
C8 C9 C10 121.67(14) . . ?
C9 C9 C10 119.52(16) 5_565 . ?
C12 C8 C9 120.77(14) . . ?
C12 C8 C7 119.90(13) . . ?
C9 C8 C7 119.33(14) . . ?
C13 C10 C9 120.31(14) . . ?
C13 C10 C11 120.03(14) . . ?
C9 C10 C11 119.63(13) . . ?
O1 C7 N2 120.29(13) . . ?
O1 C7 C8 122.77(14) . . ?
N2 C7 C8 116.94(13) . . ?
N2 C6 C5 114.68(12) . . ?
N2 C6 H6A 108.6 . . ?
C5 C6 H6A 108.6 . . ?
N2 C6 H6B 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C10 C13 C12 120.47(14) . 5_565 ?
C10 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 5_565 . ?
O2 C11 N2 120.51(13) . . ?
O2 C11 C10 122.68(14) . . ?
N2 C11 C10 116.81(13) . . ?
C8 C12 C13 120.10(13) . 5_565 ?
C8 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 5_565 . ?
C5 C1 C2 119.58(15) . . ?
C5 C1 H1A 120.2 . . ?
C2 C1 H1A 120.2 . . ?
C3 N1 C2 116.23(14) . . ?
C1 C5 C4 117.23(14) . . ?
C1 C5 C6 118.77(14) . . ?
C4 C5 C6 123.95(13) . . ?
C5 C4 C3 119.25(14) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
N1 C3 C4 123.90(15) . . ?
N1 C3 H3A 118.0 . . ?
C4 C3 H3A 118.0 . . ?
N1 C2 C1 123.76(14) . . ?
N1 C2 H2A 118.1 . . ?
C1 C2 H2A 118.1 . . ?
H1B O1W H1C 105(2) . . ?

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 C9 C8 C12 -0.5(2) 5_565 . . . ?
C10 C9 C8 C12 179.26(13) . . . . ?
C9 C9 C8 C7 179.28(14) 5_565 . . . ?
C10 C9 C8 C7 -1.0(2) . . . . ?
C8 C9 C10 C13 179.61(13) . . . . ?
C9 C9 C10 C13 -0.7(2) 5_565 . . . ?
C8 C9 C10 C11 -2.3(2) . . . . ?
C9 C9 C10 C11 177.41(15) 5_565 . . . ?
C11 N2 C7 O1 175.82(13) . . . . ?
C6 N2 C7 O1 -5.8(2) . . . . ?
C11 N2 C7 C8 -3.8(2) . . . . ?
C6 N2 C7 C8 174.52(12) . . . . ?
C12 C8 C7 O1 4.1(2) . . . . ?
C9 C8 C7 O1 -175.68(13) . . . . ?
C12 C8 C7 N2 -176.30(12) . . . . ?
C9 C8 C7 N2 4.0(2) . . . . ?
C11 N2 C6 C5 -96.99(16) . . . . ?
C7 N2 C6 C5 84.52(16) . . . . ?
C9 C10 C13 C12 0.3(2) . . . 5_565 ?
C11 C10 C13 C12 -177.73(13) . . . 5_565 ?
C7 N2 C11 O2 179.75(13) . . . . ?
C6 N2 C11 O2 1.4(2) . . . . ?
C7 N2 C11 C10 0.6(2) . . . . ?
C6 N2 C11 C10 -177.72(12) . . . . ?
C13 C10 C11 O2 1.5(2) . . . . ?
C9 C10 C11 O2 -176.55(13) . . . . ?
C13 C10 C11 N2 -179.35(12) . . . . ?
C9 C10 C11 N2 2.6(2) . . . . ?
C9 C8 C12 C13 0.8(2) . . . 5_565 ?
C7 C8 C12 C13 -178.94(13) . . . 5_565 ?
C2 C1 C5 C4 -1.4(2) . . . . ?
C2 C1 C5 C6 -179.19(15) . . . . ?
N2 C6 C5 C1 -161.14(14) . . . . ?
N2 C6 C5 C4 21.2(2) . . . . ?
C1 C5 C4 C3 1.8(2) . . . . ?
C6 C5 C4 C3 179.45(15) . . . . ?
C2 N1 C3 C4 -1.1(3) . . . . ?
C5 C4 C3 N1 -0.6(3) . . . . ?
C3 N1 C2 C1 1.5(3) . . . . ?
C5 C1 C2 N1 -0.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        59.97
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.198
_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_2
_database_code_depnum_ccdc_archive 'CCDC 1507743'
_audit_update_record             
;
2016-10-02 deposited with the CCDC.
2017-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H16 N4 O4'
_chemical_formula_weight         448.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   22.760(8)
_cell_length_b                   4.6927(12)
_cell_length_c                   21.335(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.96(5)
_cell_angle_gamma                90.00
_cell_volume                     2048.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    373(2)
_cell_measurement_reflns_used    514
_cell_measurement_theta_min      3.9031
_cell_measurement_theta_max      62.6698

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.20051
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      373(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Oxford
_diffrn_measurement_method       'ω and π scan'
_diffrn_detector_area_resol_mean 16.0855
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            4003
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.32
_diffrn_reflns_theta_max         59.98
_reflns_number_total             1507
_reflns_number_gt                892
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.1630P)²+0.0000P] 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         1507
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0888
_refine_ls_wR_factor_ref         0.2899
_refine_ls_wR_factor_gt          0.2442
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.8144(2) -0.0339(8) -0.0048(2) 0.1011(13) Uani 1 1 d . . .
N2 N 0.8934(2) 0.2668(8) 0.0658(2) 0.0783(12) Uani 1 1 d . . .
O2 O 0.9725(2) 0.5652(9) 0.1362(2) 0.1111(14) Uani 1 1 d . . .
C10 C 1.0016(2) 0.2587(10) 0.0669(2) 0.0736(13) Uani 1 1 d . . .
C9 C 0.9787(2) 0.0523(9) 0.0135(2) 0.0676(12) Uani 1 1 d . . .
C8 C 0.9138(2) -0.0473(10) -0.0141(2) 0.0707(13) Uani 1 1 d . . .
C11 C 0.9567(3) 0.3774(12) 0.0930(3) 0.0807(14) Uani 1 1 d . . .
C7 C 0.8693(3) 0.0552(11) 0.0143(3) 0.0783(14) Uani 1 1 d . . .
C5 C 0.8463(3) 0.1997(11) 0.1504(3) 0.0811(14) Uani 1 1 d . . .
C6 C 0.8483(3) 0.3763(11) 0.0930(3) 0.0859(15) Uani 1 1 d . . .
H6A H 0.8047 0.3857 0.0550 0.103 Uiso 1 1 calc R . .
H6B H 0.8613 0.5687 0.1101 0.103 Uiso 1 1 calc R . .
C13 C 1.1075(3) 0.2444(10) 0.0673(3) 0.0818(14) Uani 1 1 d . . .
H13A H 1.1504 0.3088 0.0859 0.098 Uiso 1 1 calc R . .
C12 C 1.0652(3) 0.3489(11) 0.0938(3) 0.0851(15) Uani 1 1 d . . .
H12A H 1.0804 0.4808 0.1300 0.102 Uiso 1 1 calc R . .
N1 N 0.8406(4) -0.1064(14) 0.2600(3) 0.1191(18) Uani 1 1 d . . .
C4 C 0.8990(3) 0.0555(14) 0.1978(3) 0.1058(19) Uani 1 1 d . . .
H4A H 0.9384 0.0574 0.1942 0.127 Uiso 1 1 calc R . .
C3 C 0.8940(4) -0.0922(16) 0.2505(3) 0.115(2) Uani 1 1 d . . .
H3A H 0.9308 -0.1893 0.2818 0.138 Uiso 1 1 calc R . .
C1 C 0.7915(3) 0.1940(14) 0.1604(4) 0.112(2) Uani 1 1 d . . .
H1A H 0.7546 0.2934 0.1302 0.135 Uiso 1 1 calc R . .
C2 C 0.7900(4) 0.0427(18) 0.2148(5) 0.126(2) Uani 1 1 d . . .
H2A H 0.7517 0.0447 0.2204 0.151 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.079(3) 0.113(3) 0.122(3) 0.000(2) 0.054(2) -0.001(2)
N2 0.076(3) 0.078(2) 0.087(3) 0.012(2) 0.042(2) 0.009(2)
O2 0.109(3) 0.117(3) 0.117(3) -0.036(3) 0.058(3) -0.015(2)
C10 0.076(3) 0.072(3) 0.076(3) 0.009(2) 0.037(2) -0.003(2)
C9 0.074(3) 0.064(2) 0.065(3) 0.011(2) 0.030(2) -0.002(2)
C8 0.070(3) 0.071(3) 0.069(3) 0.011(2) 0.029(2) -0.003(2)
C11 0.081(4) 0.087(3) 0.080(3) 0.002(3) 0.040(3) -0.002(3)
C7 0.075(4) 0.078(3) 0.084(3) 0.018(3) 0.037(3) 0.006(3)
C5 0.087(4) 0.077(3) 0.086(3) -0.005(3) 0.044(3) 0.004(3)
C6 0.078(3) 0.087(3) 0.097(4) 0.014(3) 0.043(3) 0.016(3)
C13 0.077(3) 0.079(3) 0.086(3) 0.002(3) 0.032(3) -0.016(2)
C12 0.093(4) 0.084(3) 0.080(3) -0.007(3) 0.039(3) -0.005(3)
N1 0.128(5) 0.136(4) 0.112(4) 0.006(3) 0.070(4) -0.001(4)
C4 0.096(4) 0.128(5) 0.102(4) 0.023(4) 0.051(4) 0.014(4)
C3 0.116(5) 0.133(5) 0.099(5) 0.025(4) 0.048(4) 0.023(4)
C1 0.103(5) 0.131(5) 0.116(5) 0.021(4) 0.059(4) 0.024(4)
C2 0.118(6) 0.150(6) 0.142(6) 0.010(5) 0.087(5) 0.005(5)

_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 C7 1.208(6) . ?
N2 C11 1.397(7) . ?
N2 C7 1.403(7) . ?
N2 C6 1.474(6) . ?
O2 C11 1.210(6) . ?
C10 C12 1.370(7) . ?
C10 C9 1.410(7) . ?
C10 C11 1.471(7) . ?
C9 C9 1.415(9) 5_755 ?
C9 C8 1.410(7) . ?
C8 C13 1.378(7) 5_755 ?
C8 C7 1.468(7) . ?
C5 C4 1.363(8) . ?
C5 C1 1.354(8) . ?
C5 C6 1.495(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C13 C8 1.378(7) 5_755 ?
C13 C12 1.400(7) . ?
C13 H13A 0.9300 . ?
C12 H12A 0.9300 . ?
N1 C3 1.318(8) . ?
N1 C2 1.331(10) . ?
C4 C3 1.369(9) . ?
C4 H4A 0.9300 . ?
C3 H3A 0.9300 . ?
C1 C2 1.375(10) . ?
C1 H1A 0.9300 . ?
C2 H2A 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
C11 N2 C7 124.5(4) . . ?
C11 N2 C6 118.4(5) . . ?
C7 N2 C6 117.1(4) . . ?
C12 C10 C9 120.0(5) . . ?
C12 C10 C11 120.4(5) . . ?
C9 C10 C11 119.6(5) . . ?
C9 C9 C10 119.3(5) 5_755 . ?
C9 C9 C8 119.7(6) 5_755 . ?
C10 C9 C8 121.0(5) . . ?
C13 C8 C9 119.5(5) 5_755 . ?
C13 C8 C7 120.2(5) 5_755 . ?
C9 C8 C7 120.3(5) . . ?
O2 C11 N2 119.7(5) . . ?
O2 C11 C10 122.7(5) . . ?
N2 C11 C10 117.6(5) . . ?
O1 C7 N2 120.0(5) . . ?
O1 C7 C8 123.1(5) . . ?
N2 C7 C8 116.9(5) . . ?
C4 C5 C1 116.5(5) . . ?
C4 C5 C6 123.4(5) . . ?
C1 C5 C6 120.0(5) . . ?
N2 C6 C5 113.9(4) . . ?
N2 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
N2 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C8 C13 C12 120.8(5) 5_755 . ?
C8 C13 H13A 119.6 5_755 . ?
C12 C13 H13A 119.6 . . ?
C10 C12 C13 120.6(5) . . ?
C10 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C3 N1 C2 115.2(6) . . ?
C5 C4 C3 119.8(6) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
N1 C3 C4 124.5(6) . . ?
N1 C3 H3A 117.8 . . ?
C4 C3 H3A 117.8 . . ?
C5 C1 C2 120.6(6) . . ?
C5 C1 H1A 119.7 . . ?
C2 C1 H1A 119.7 . . ?
N1 C2 C1 123.3(7) . . ?
N1 C2 H2A 118.3 . . ?
C1 C2 H2A 118.3 . . ?

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
C12 C10 C9 C9 -2.2(8) . . . 5_755 ?
C11 C10 C9 C9 177.3(5) . . . 5_755 ?
C12 C10 C9 C8 178.9(4) . . . . ?
C11 C10 C9 C8 -1.6(7) . . . . ?
C9 C9 C8 C13 -0.3(8) 5_755 . . 5_755 ?
C10 C9 C8 C13 178.6(4) . . . 5_755 ?
C9 C9 C8 C7 178.8(4) 5_755 . . . ?
C10 C9 C8 C7 -2.3(7) . . . . ?
C7 N2 C11 O2 178.1(4) . . . . ?
C6 N2 C11 O2 -2.4(7) . . . . ?
C7 N2 C11 C10 -1.5(7) . . . . ?
C6 N2 C11 C10 178.0(4) . . . . ?
C12 C10 C11 O2 3.4(8) . . . . ?
C9 C10 C11 O2 -176.1(5) . . . . ?
C12 C10 C11 N2 -177.0(4) . . . . ?
C9 C10 C11 N2 3.5(7) . . . . ?
C11 N2 C7 O1 177.9(4) . . . . ?
C6 N2 C7 O1 -1.7(6) . . . . ?
C11 N2 C7 C8 -2.2(7) . . . . ?
C6 N2 C7 C8 178.3(4) . . . . ?
C13 C8 C7 O1 3.2(7) 5_755 . . . ?
C9 C8 C7 O1 -175.9(4) . . . . ?
C13 C8 C7 N2 -176.7(4) 5_755 . . . ?
C9 C8 C7 N2 4.1(6) . . . . ?
C11 N2 C6 C5 -94.9(6) . . . . ?
C7 N2 C6 C5 84.7(5) . . . . ?
C4 C5 C6 N2 32.8(8) . . . . ?
C1 C5 C6 N2 -152.1(5) . . . . ?
C9 C10 C12 C13 1.9(7) . . . . ?
C11 C10 C12 C13 -177.6(4) . . . . ?
C8 C13 C12 C10 -0.5(7) 5_755 . . . ?
C1 C5 C4 C3 2.1(9) . . . . ?
C6 C5 C4 C3 177.3(6) . . . . ?
C2 N1 C3 C4 -1.8(10) . . . . ?
C5 C4 C3 N1 -0.3(11) . . . . ?
C4 C5 C1 C2 -1.7(9) . . . . ?
C6 C5 C1 C2 -177.1(6) . . . . ?
C3 N1 C2 C1 2.2(11) . . . . ?
C5 C1 C2 N1 -0.5(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        59.98
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.061
