# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 
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data_sd_ak2786bl2_1058069
_database_code_depnum_ccdc_archive 'CCDC 1058069'
_audit_update_record             
;
2015-08-06 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_sd_ak2786bl2_1058069 
;
PROBLEM: Ratio Observed / Unique Reflections too Low .... 39 %
RESPONSE: The crystal quality was not sufficiently good enough and it 
diffracted poorly at higher angle. 
Otherwise, no reflection was removed intentionally.
;
_vrf_PLAT230_sd_ak2786bl2_1058069 
;
PROBLEM: Hirshfeld Test Diff for N6 -- C6 .. 7.5 su
RESPONSE: The atoms were assigned correctly. 
Due to the polar nature of the bonds, the anisotropic displacement 
parameters along the bonds are not equal. 
Further, we do not observe any disorder in this region.
;
# end Validation Reply Form
_audit_creation_date             2015-08-04
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.07.23 svn.r3196 for OlexSys, GUI svn.r5077)
;
_chemical_name_common            5e
_chemical_name_systematic        
'(E)-methyl 2-(4-benzyl-1-(3-(dimethylamino)propyl)-8-nitro-3- oxo-3,4-dihydropyrazino[2,3-b]quinoxalin-2(1H)-ylidene)acetate'
_chemical_formula_moiety         'C25 H26 N6 O5'
_chemical_formula_sum            'C25 H26 N6 O5'
_chemical_formula_weight         490.52
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8603(5)
_cell_length_b                   11.0162(13)
_cell_length_c                   19.371(2)
_cell_angle_alpha                76.719(7)
_cell_angle_beta                 87.487(6)
_cell_angle_gamma                80.980(6)
_cell_volume                     1202.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3410
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.17
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1233 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.8961.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0924
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23939
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_min         1.080
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2157
_reflns_number_total             5490
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5490
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1671
_refine_ls_R_factor_gt           0.0558
_refine_ls_restrained_S_all      0.943
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0824P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1831
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C11(H11A,H11B), C22(H22A,H22B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C5(H5), C8(H8), C7(H7), C13(H13), C17(H17), C14(H14), C16(H16),
 C15(H15)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 1.1090(2) 0.42769(16) 0.10131(10) 0.0614(5) Uani 1 1 d . . . . .
O1 O 0.8958(3) 0.68216(16) 0.10617(9) 0.0647(5) Uani 1 1 d . . . . .
N1 N 0.5641(3) 0.74006(18) 0.16261(10) 0.0461(5) Uani 1 1 d . . . . .
N2 N 0.6927(3) 0.53781(17) 0.27926(10) 0.0460(5) Uani 1 1 d . . . . .
N4 N 0.2215(3) 0.79580(18) 0.22013(10) 0.0481(5) Uani 1 1 d . . . . .
N3 N 0.3500(3) 0.59198(18) 0.33674(10) 0.0498(5) Uani 1 1 d . . . . .
O2 O 1.3758(3) 0.50756(19) 0.14896(11) 0.0808(6) Uani 1 1 d . . . . .
N5 N 1.0638(3) 0.1789(2) 0.36782(13) 0.0630(6) Uani 1 1 d . . . . .
C10 C 0.4154(4) 0.7184(2) 0.22092(12) 0.0426(6) Uani 1 1 d . . . . .
O5 O -0.5572(3) 0.7766(2) 0.45265(11) 0.0970(7) Uani 1 1 d . . . . .
N6 N -0.3734(4) 0.7057(3) 0.45457(15) 0.0729(7) Uani 1 1 d . . . . .
C4 C 0.1445(3) 0.6722(2) 0.33696(13) 0.0454(6) Uani 1 1 d . . . . .
C3 C 0.4834(3) 0.6148(2) 0.28062(13) 0.0440(6) Uani 1 1 d . . . . .
C9 C 0.0794(3) 0.7723(2) 0.27900(13) 0.0447(6) Uani 1 1 d . . . . .
C2 C 0.8339(3) 0.5504(2) 0.21833(13) 0.0455(6) Uani 1 1 d . . . . .
C12 C 0.5778(4) 0.9670(2) 0.10731(12) 0.0489(6) Uani 1 1 d . . . . .
C1 C 0.7682(4) 0.6611(2) 0.15795(14) 0.0488(6) Uani 1 1 d . . . . .
C19 C 1.1870(4) 0.4756(2) 0.15175(15) 0.0546(7) Uani 1 1 d . . . . .
C18 C 1.0283(4) 0.4707(2) 0.21322(14) 0.0537(7) Uani 1 1 d . . . . .
H18 H 1.0673 0.4052 0.2526 0.064 Uiso 1 1 calc R . . . .
C6 C -0.2114(4) 0.7297(3) 0.39460(14) 0.0531(7) Uani 1 1 d . . . . .
O4 O -0.3182(4) 0.6177(3) 0.50431(13) 0.1186(10) Uani 1 1 d . . . . .
C5 C -0.0044(4) 0.6519(2) 0.39603(14) 0.0527(7) Uani 1 1 d . . . . .
H5 H 0.0371 0.5867 0.4354 0.063 Uiso 1 1 calc R . . . .
C8 C -0.1347(4) 0.8513(2) 0.27976(13) 0.0530(7) Uani 1 1 d . . . . .
H8 H -0.1772 0.9181 0.2413 0.064 Uiso 1 1 calc R . . . .
C21 C 0.7551(4) 0.4303(2) 0.33984(13) 0.0552(7) Uani 1 1 d . . . . .
H21A H 0.6789 0.4498 0.3823 0.066 Uiso 1 1 calc R . . . .
H21B H 0.9205 0.4184 0.3472 0.066 Uiso 1 1 calc R . . . .
C11 C 0.4932(4) 0.8470(2) 0.10134(13) 0.0534(7) Uani 1 1 d . . . . .
H11A H 0.3260 0.8623 0.0984 0.064 Uiso 1 1 calc R . . . .
H11B H 0.5539 0.8240 0.0579 0.064 Uiso 1 1 calc R . . . .
C7 C -0.2797(4) 0.8298(3) 0.33706(15) 0.0580(7) Uani 1 1 d . . . . .
H7 H -0.4216 0.8810 0.3378 0.070 Uiso 1 1 calc R . . . .
C13 C 0.7818(4) 1.0001(3) 0.07508(14) 0.0673(8) Uani 1 1 d . . . . .
H13 H 0.8670 0.9484 0.0484 0.081 Uiso 1 1 calc R . . . .
C17 C 0.4572(4) 1.0474(3) 0.14687(15) 0.0660(8) Uani 1 1 d . . . . .
H17 H 0.3185 1.0288 0.1688 0.079 Uiso 1 1 calc R . . . .
C22 C 0.6874(4) 0.3075(3) 0.32885(15) 0.0660(8) Uani 1 1 d . . . . .
H22A H 0.5222 0.3093 0.3360 0.079 Uiso 1 1 calc R . . . .
H22B H 0.7239 0.3001 0.2805 0.079 Uiso 1 1 calc R . . . .
C23 C 0.8139(4) 0.1944(3) 0.37982(16) 0.0726(9) Uani 1 1 d . . . . .
H23A H 0.7815 0.2038 0.4280 0.087 Uiso 1 1 calc R . . . .
H23B H 0.7566 0.1190 0.3747 0.087 Uiso 1 1 calc R . . . .
C14 C 0.8612(5) 1.1087(3) 0.08190(17) 0.0823(10) Uani 1 1 d . . . . .
H14 H 0.9982 1.1292 0.0595 0.099 Uiso 1 1 calc R . . . .
C16 C 0.5407(5) 1.1548(3) 0.15415(17) 0.0793(9) Uani 1 1 d . . . . .
H16 H 0.4595 1.2061 0.1818 0.095 Uiso 1 1 calc R . . . .
C15 C 0.7408(5) 1.1862(3) 0.12114(17) 0.0769(9) Uani 1 1 d . . . . .
H15 H 0.7944 1.2593 0.1253 0.092 Uiso 1 1 calc R . . . .
C20 C 1.2523(4) 0.4310(3) 0.03806(15) 0.0880(10) Uani 1 1 d . . . . .
H20A H 1.1909 0.3865 0.0077 0.132 Uiso 1 1 calc GR . . . .
H20B H 1.4070 0.3916 0.0513 0.132 Uiso 1 1 calc GR . . . .
H20C H 1.2539 0.5171 0.0133 0.132 Uiso 1 1 calc GR . . . .
C24 C 1.1355(5) 0.1149(3) 0.31175(19) 0.1030(12) Uani 1 1 d . . . . .
H24A H 1.1029 0.0298 0.3253 0.154 Uiso 1 1 calc GR . . . .
H24B H 1.2984 0.1138 0.3034 0.154 Uiso 1 1 calc GR . . . .
H24C H 1.0531 0.1583 0.2692 0.154 Uiso 1 1 calc GR . . . .
C25 C 1.1841(5) 0.1082(4) 0.43276(19) 0.1125(12) Uani 1 1 d . . . . .
H25A H 1.1397 0.1506 0.4705 0.169 Uiso 1 1 calc GR . . . .
H25B H 1.3479 0.1029 0.4250 0.169 Uiso 1 1 calc GR . . . .
H25C H 1.1435 0.0248 0.4454 0.169 Uiso 1 1 calc GR . . . .


_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
O3 C19 1.339(3) . ?
O3 C20 1.451(3) . ?
O1 C1 1.225(3) . ?
N1 C10 1.395(3) . ?
N1 C1 1.377(3) . ?
N1 C11 1.489(3) . ?
N2 C3 1.380(3) . ?
N2 C2 1.404(3) . ?
N2 C21 1.475(3) . ?
N4 C10 1.308(3) . ?
N4 C9 1.382(3) . ?
N3 C4 1.378(3) . ?
N3 C3 1.311(3) . ?
O2 C19 1.208(3) . ?
N5 C23 1.462(3) . ?
N5 C24 1.440(3) . ?
N5 C25 1.463(4) . ?
C10 C3 1.446(3) . ?
O5 N6 1.224(3) . ?
N6 C6 1.470(3) . ?
N6 O4 1.213(3) . ?
C4 C9 1.400(3) . ?
C4 C5 1.406(3) . ?
C9 C8 1.412(3) . ?
C2 C1 1.497(3) . ?
C2 C18 1.340(3) . ?
C12 C11 1.512(3) . ?
C12 C13 1.385(3) . ?
C12 C17 1.393(3) . ?
C19 C18 1.475(3) . ?
C18 H18 0.9300 . ?
C6 C5 1.369(3) . ?
C6 C7 1.398(3) . ?
C5 H5 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.367(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.530(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C7 H7 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.385(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.387(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.512(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C14 H14 0.9300 . ?
C14 C15 1.366(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.365(4) . ?
C15 H15 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
C19 O3 C20 115.96(19) . . ?
C10 N1 C11 119.08(18) . . ?
C1 N1 C10 122.1(2) . . ?
C1 N1 C11 118.7(2) . . ?
C3 N2 C2 121.4(2) . . ?
C3 N2 C21 118.99(18) . . ?
C2 N2 C21 119.18(18) . . ?
C10 N4 C9 116.7(2) . . ?
C3 N3 C4 117.2(2) . . ?
C23 N5 C25 110.3(2) . . ?
C24 N5 C23 113.0(2) . . ?
C24 N5 C25 108.5(2) . . ?
N1 C10 C3 119.34(19) . . ?
N4 C10 N1 118.2(2) . . ?
N4 C10 C3 122.5(2) . . ?
O5 N6 C6 118.5(3) . . ?
O4 N6 O5 122.7(3) . . ?
O4 N6 C6 118.8(2) . . ?
N3 C4 C9 121.3(2) . . ?
N3 C4 C5 119.4(2) . . ?
C9 C4 C5 119.4(2) . . ?
N2 C3 C10 120.0(2) . . ?
N3 C3 N2 118.7(2) . . ?
N3 C3 C10 121.3(2) . . ?
N4 C9 C4 121.1(2) . . ?
N4 C9 C8 118.7(2) . . ?
C4 C9 C8 120.2(2) . . ?
N2 C2 C1 118.12(19) . . ?
C18 C2 N2 122.9(2) . . ?
C18 C2 C1 119.0(2) . . ?
C13 C12 C11 121.4(2) . . ?
C13 C12 C17 117.1(3) . . ?
C17 C12 C11 121.5(2) . . ?
O1 C1 N1 120.8(2) . . ?
O1 C1 C2 120.6(2) . . ?
N1 C1 C2 118.6(2) . . ?
O3 C19 C18 112.2(2) . . ?
O2 C19 O3 122.7(2) . . ?
O2 C19 C18 124.8(2) . . ?
C2 C18 C19 126.9(2) . . ?
C2 C18 H18 116.5 . . ?
C19 C18 H18 116.5 . . ?
C5 C6 N6 119.3(3) . . ?
C5 C6 C7 122.6(2) . . ?
C7 C6 N6 118.0(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.8(2) . . ?
C6 C5 H5 120.6 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 120.0(2) . . ?
C7 C8 H8 120.0 . . ?
N2 C21 H21A 109.0 . . ?
N2 C21 H21B 109.0 . . ?
N2 C21 C22 112.8(2) . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
N1 C11 C12 112.53(19) . . ?
N1 C11 H11A 109.1 . . ?
N1 C11 H11B 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 119.0(2) . . ?
C8 C7 H7 120.5 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13 119.4 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 121.1(2) . . ?
C16 C17 H17 119.5 . . ?
C21 C22 H22A 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C23 C22 C21 111.1(2) . . ?
C23 C22 H22A 109.4 . . ?
C23 C22 H22B 109.4 . . ?
N5 C23 C22 112.5(2) . . ?
N5 C23 H23A 109.1 . . ?
N5 C23 H23B 109.1 . . ?
C22 C23 H23A 109.1 . . ?
C22 C23 H23B 109.1 . . ?
H23A C23 H23B 107.8 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C17 C16 H16 119.6 . . ?
C15 C16 C17 120.7(3) . . ?
C15 C16 H16 119.6 . . ?
C14 C15 C16 119.1(3) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N5 C24 H24A 109.5 . . ?
N5 C24 H24B 109.5 . . ?
N5 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N5 C25 H25A 109.5 . . ?
N5 C25 H25B 109.5 . . ?
N5 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
O3 C19 C18 C2 -79.8(3) . . . . ?
N1 C10 C3 N2 -0.6(3) . . . . ?
N1 C10 C3 N3 179.25(19) . . . . ?
N2 C2 C1 O1 173.83(19) . . . . ?
N2 C2 C1 N1 -4.8(3) . . . . ?
N2 C2 C18 C19 179.8(2) . . . . ?
N2 C21 C22 C23 162.99(19) . . . . ?
N4 C10 C3 N2 -178.4(2) . . . . ?
N4 C10 C3 N3 1.4(3) . . . . ?
N4 C9 C8 C7 179.5(2) . . . . ?
N3 C4 C9 N4 -1.4(3) . . . . ?
N3 C4 C9 C8 178.4(2) . . . . ?
N3 C4 C5 C6 -177.8(2) . . . . ?
O2 C19 C18 C2 106.8(3) . . . . ?
C10 N1 C1 O1 180.0(2) . . . . ?
C10 N1 C1 C2 -1.4(3) . . . . ?
C10 N1 C11 C12 92.2(2) . . . . ?
C10 N4 C9 C4 1.5(3) . . . . ?
C10 N4 C9 C8 -178.30(19) . . . . ?
O5 N6 C6 C5 179.6(2) . . . . ?
O5 N6 C6 C7 -2.4(4) . . . . ?
N6 C6 C5 C4 177.1(2) . . . . ?
N6 C6 C7 C8 -178.0(2) . . . . ?
C4 N3 C3 N2 178.67(18) . . . . ?
C4 N3 C3 C10 -1.2(3) . . . . ?
C4 C9 C8 C7 -0.3(3) . . . . ?
C3 N2 C2 C1 8.4(3) . . . . ?
C3 N2 C2 C18 -174.2(2) . . . . ?
C3 N2 C21 C22 93.4(2) . . . . ?
C3 N3 C4 C9 1.2(3) . . . . ?
C3 N3 C4 C5 -179.87(19) . . . . ?
C9 N4 C10 N1 -179.38(17) . . . . ?
C9 N4 C10 C3 -1.5(3) . . . . ?
C9 C4 C5 C6 1.1(3) . . . . ?
C9 C8 C7 C6 0.6(4) . . . . ?
C2 N2 C3 N3 174.33(19) . . . . ?
C2 N2 C3 C10 -5.8(3) . . . . ?
C2 N2 C21 C22 -79.0(2) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
C12 C17 C16 C15 1.7(4) . . . . ?
C1 N1 C10 N4 -177.91(19) . . . . ?
C1 N1 C10 C3 4.2(3) . . . . ?
C1 N1 C11 C12 -91.7(2) . . . . ?
C1 C2 C18 C19 -2.9(4) . . . . ?
C18 C2 C1 O1 -3.6(3) . . . . ?
C18 C2 C1 N1 177.8(2) . . . . ?
O4 N6 C6 C5 0.6(4) . . . . ?
O4 N6 C6 C7 178.7(3) . . . . ?
C5 C4 C9 N4 179.65(19) . . . . ?
C5 C4 C9 C8 -0.5(3) . . . . ?
C5 C6 C7 C8 0.0(4) . . . . ?
C21 N2 C3 N3 2.1(3) . . . . ?
C21 N2 C3 C10 -178.11(19) . . . . ?
C21 N2 C2 C1 -179.33(18) . . . . ?
C21 N2 C2 C18 -2.0(3) . . . . ?
C21 C22 C23 N5 -64.3(3) . . . . ?
C11 N1 C10 N4 -2.0(3) . . . . ?
C11 N1 C10 C3 -179.91(19) . . . . ?
C11 N1 C1 O1 4.0(3) . . . . ?
C11 N1 C1 C2 -177.38(19) . . . . ?
C11 C12 C13 C14 -178.6(3) . . . . ?
C11 C12 C17 C16 177.6(2) . . . . ?
C7 C6 C5 C4 -0.9(4) . . . . ?
C13 C12 C11 N1 94.9(3) . . . . ?
C13 C12 C17 C16 -0.8(4) . . . . ?
C13 C14 C15 C16 0.4(5) . . . . ?
C17 C12 C11 N1 -83.4(3) . . . . ?
C17 C12 C13 C14 -0.2(4) . . . . ?
C17 C16 C15 C14 -1.4(4) . . . . ?
C20 O3 C19 O2 -7.7(4) . . . . ?
C20 O3 C19 C18 178.8(2) . . . . ?
C24 N5 C23 C22 -82.6(3) . . . . ?
C25 N5 C23 C22 155.7(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform, methanol'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_sd_ak2786ond2_1058070
_database_code_depnum_ccdc_archive 'CCDC 1058070'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;
_audit_creation_date             2015-08-04
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.07.23 svn.r3196 for OlexSys, GUI svn.r5077)
;
_chemical_name_common            ?
_chemical_name_systematic        
'(E)-methyl 2-(4-benzyl-1-(3-(dimethylamino)propyl)-8-nitro-3-oxo-3,4-dihydropyrazino[2,3-b]quinoxalin-2(1H)-ylidene)acetate '
_chemical_formula_moiety         'C16 H15 N5 O3'
_chemical_formula_sum            'C16 H15 N5 O3'
_chemical_formula_weight         325.33
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.4267(9)
_cell_length_b                   10.4362(12)
_cell_length_c                   17.949(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.189(7)
_cell_angle_gamma                90
_cell_volume                     1553.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3583
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.26
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0735 before and 0.0529 after correction.
The Ratio of minimum to maximum transmission is 0.9124.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15689
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.464
_diffrn_reflns_theta_min         2.306
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                3929
_reflns_number_total             6998
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1400 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         6998
_refine_ls_number_restraints     239
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      0.954
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0576P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1245
_refine_special_details          
;           
The asymmetric unit contains two independent molecules.
A five membered ring O3 C13 C14 C15 C16 in RESI_1 is disordered over two positions.
The disordered components were restrained to have similar bond lengths (SADI) and similar Uij (SIMU).
Two atoms, C3 and C4, which are part of a six membered sing in RESI_2 are disordered over two positions.
These atoms are refined with rigid body model (RIGU) to have similar bond lengths and angles
with their neighbouring atoms, N3_2 and C5_2, to those of RESI_1 using SAME command.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
2. Restrained distances
 C13B_1-C12_1 \\sim C13A_1-C12_1
 with sigma of 0.02
 C14B_1-C13B_1 \\sim C14A_1-C13A_1
 with sigma of 0.02
 C15B_1-C14B_1 \\sim C15A_1-C14A_1
 with sigma of 0.02
 C16A_1-C15A_1 \\sim C16B_1-C15B_1
 with sigma of 0.02
 O3B_1-C16B_1 \\sim O3A_1-C16A_1
 with sigma of 0.02
 O3B_1-C13B_1 \\sim O3A_1-C13A_1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C13B_1 \\sim C14B_1 \\sim C15B_1 \\sim C16B_1 \\sim O3B_1 \\sim C13A_1 \\sim
C14A_1 \\sim C15A_1 \\sim C16A_1 \\sim O3A_1: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.04
C3A_2 \\sim C4B_2: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04
C4A_2 \\sim C3B_2: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04
4. Rigid body (RIGU) restrains
 C3A_2, C4B_2
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 C4A_2, C3B_2
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 C13B_1, C14B_1, C15B_1, C16B_1, O3B_1, C13A_1, C14A_1, C15A_1, C16A_1, O3A_1
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
5. Same fragment restrains
{N3_1, C3_1, C4_1, C5_1} sigma for 1-2: 0.02, 1-3: 0.04
as
{N3_2, C3A_2, C4A_2, C3B_2}
6. Others
 Sof(H12C)=Sof(H12D)=Sof(C13B)=Sof(O3B)=Sof(C16B)=Sof(H16B)=Sof(C15B)=
 Sof(H15B)=Sof(C14B)=Sof(H14B)=1-FVAR(1)
 Sof(H12A)=Sof(H12B)=Sof(C13A)=Sof(O3A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15A)=Sof(C16A)=Sof(H16A)=FVAR(1)
 Sof(C3B)=Sof(H3BA)=Sof(H3BB)=Sof(C4B)=Sof(H4BA)=Sof(H4BB)=Sof(H5BC)=Sof(H5BD)=
 1-FVAR(2)
 Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(H5AA)=Sof(H5AB)=
 FVAR(2)
7.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C12(H12A,H12B), C12(H12C,H12D),
 C3A(H3AA,H3AB), C4A(H4AA,H4AB), C3B(H3BA,H3BB), C4B(H4BA,H4BB), C5(H5AA,H5AB),
 C5(H5BC,H5BD), C12(H12A,H12B)
7.b Aromatic/amide H refined with riding coordinates:
 N4(H4), C7(H7), C9(H9), C10(H10), C14A(H14A), C15A(H15A), C16A(H16A),
 C16B(H16B), C15B(H15B), C14B(H14B), N4(H4), C7(H7), C9(H9), C10(H10), C14(H14),
  C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1_1 O -1.0289(4) -0.4892(4) -0.4957(2) 0.1073(12) Uani 1 1 d . . . . .
O2_1 O -0.9919(4) -0.2977(5) -0.5345(2) 0.1158(14) Uani 1 1 d . . . . .
N1_1 N -0.4770(3) -0.3205(3) -0.23158(17) 0.0542(8) Uani 1 1 d . . . . .
N3_1 N -0.4193(3) 0.0216(4) -0.22923(18) 0.0626(9) Uani 1 1 d D . . . .
C3_1 C -0.4813(5) 0.1377(5) -0.2706(3) 0.0774(12) Uani 1 1 d D . . . .
H3A_1 H -0.4228 0.1521 -0.3118 0.093 Uiso 1 1 calc R U . . .
H3B_1 H -0.4629 0.2108 -0.2368 0.093 Uiso 1 1 calc R U . . .
C4_1 C -0.6587(5) 0.1274(5) -0.3020(3) 0.0781(12) Uani 1 1 d D . . . .
H4A_1 H -0.6943 0.2038 -0.3310 0.094 Uiso 1 1 calc R U . . .
H4B_1 H -0.7186 0.1211 -0.2608 0.094 Uiso 1 1 calc R U . . .
C5_1 C -0.6922(4) 0.0111(4) -0.3523(2) 0.0644(11) Uani 1 1 d D . . . .
H5A_1 H -0.8074 -0.0042 -0.3638 0.077 Uiso 1 1 calc R U . . .
H5B_1 H -0.6544 0.0264 -0.3995 0.077 Uiso 1 1 calc R U . . .
N4_1 N -0.3110(3) -0.1857(4) -0.15096(17) 0.0608(9) Uani 1 1 d . . . . .
H4_1 H -0.2742 -0.1094 -0.1419 0.073 Uiso 1 1 calc R U . . .
N5_1 N -0.9584(4) -0.3847(6) -0.4898(2) 0.0786(12) Uani 1 1 d . . . . .
C1_1 C -0.4253(3) -0.2049(4) -0.2124(2) 0.0485(9) Uani 1 1 d . . . . .
C2_1 C -0.4853(3) -0.0860(4) -0.25355(19) 0.0488(9) Uani 1 1 d . . . . .
N2_1 N -0.6101(3) -0.1032(3) -0.31435(15) 0.0499(8) Uani 1 1 d . . . . .
C6_1 C -0.6621(3) -0.2256(4) -0.3391(2) 0.0478(9) Uani 1 1 d . . . . .
C7_1 C -0.7790(3) -0.2443(4) -0.40403(19) 0.0547(11) Uani 1 1 d . . . . .
H7_1 H -0.8216 -0.1751 -0.4336 0.066 Uiso 1 1 calc R U . . .
C8_1 C -0.8299(4) -0.3679(5) -0.4232(2) 0.0598(11) Uani 1 1 d . . . . .
C9_1 C -0.7675(4) -0.4748(5) -0.3829(2) 0.0680(12) Uani 1 1 d . . . . .
H9_1 H -0.8040 -0.5568 -0.3974 0.082 Uiso 1 1 calc R U . . .
C10_1 C -0.6492(4) -0.4554(4) -0.3203(2) 0.0643(11) Uani 1 1 d . . . . .
H10_1 H -0.6043 -0.5263 -0.2929 0.077 Uiso 1 1 calc R U . . .
C11_1 C -0.5939(3) -0.3331(4) -0.2964(2) 0.0502(10) Uani 1 1 d . . . . .
C12_1 C -0.2464(4) -0.2880(5) -0.0990(2) 0.0652(11) Uani 1 1 d D . . . .
H12A_1 H -0.1427 -0.2610 -0.0709 0.078 Uiso 0.380(18) 1 calc R U P A 1
H12B_1 H -0.2284 -0.3629 -0.1283 0.078 Uiso 0.380(18) 1 calc R U P A 1
H12C_1 H -0.1353 -0.2683 -0.0774 0.078 Uiso 0.620(18) 1 calc R U P A 2
H12D_1 H -0.2472 -0.3674 -0.1271 0.078 Uiso 0.620(18) 1 calc R U P A 2
C13A_1 C -0.350(6) -0.324(4) -0.045(2) 0.079(6) Uani 0.380(18) 1 d D U P A 1
O3A_1 O -0.362(2) -0.245(3) 0.0141(14) 0.100(5) Uani 0.380(18) 1 d D U P A 1
C14A_1 C -0.453(2) -0.421(2) -0.0517(13) 0.078(5) Uani 0.380(18) 1 d D U P A 1
H14A_1 H -0.4732 -0.4796 -0.0913 0.094 Uiso 0.380(18) 1 calc R U P A 1
C15A_1 C -0.523(2) -0.417(2) 0.0117(13) 0.090(5) Uani 0.380(18) 1 d D U P A 1
H15A_1 H -0.5961 -0.4760 0.0246 0.108 Uiso 0.380(18) 1 calc R U P A 1
C16A_1 C -0.469(4) -0.311(3) 0.052(2) 0.097(6) Uani 0.380(18) 1 d D U P A 1
H16A_1 H -0.4974 -0.2863 0.0981 0.117 Uiso 0.380(18) 1 calc R U P A 1
C13B_1 C -0.340(3) -0.307(2) -0.0360(11) 0.062(3) Uani 0.620(18) 1 d D U P A 2
O3B_1 O -0.3141(14) -0.2150(14) 0.0208(7) 0.088(3) Uani 0.620(18) 1 d D U P A 2
C16B_1 C -0.4101(14) -0.2476(15) 0.0745(6) 0.098(4) Uani 0.620(18) 1 d D U P A
2
H16B_1 H -0.4177 -0.2014 0.1180 0.118 Uiso 0.620(18) 1 calc R U P A 2
C15B_1 C -0.491(2) -0.3588(15) 0.0520(11) 0.090(4) Uani 0.620(18) 1 d D U P A 2
H15B_1 H -0.5626 -0.4021 0.0767 0.108 Uiso 0.620(18) 1 calc R U P A 2
C14B_1 C -0.4428(15) -0.3934(15) -0.0148(8) 0.085(3) Uani 0.620(18) 1 d D U P A
2
H14B_1 H -0.4770 -0.4673 -0.0420 0.101 Uiso 0.620(18) 1 calc R U P A 2
O1_2 O -1.5284(4) -0.1108(4) -0.5345(2) 0.1130(13) Uani 1 1 d . . . . .
O2_2 O -1.5161(4) -0.3166(4) -0.53088(18) 0.0977(10) Uani 1 1 d . . . . .
O3_2 O -0.8994(3) -0.0986(3) -0.01391(15) 0.0779(8) Uani 1 1 d . . . . .
N1_2 N -0.9812(3) -0.1707(3) -0.24971(17) 0.0531(8) Uani 1 1 d . . . . .
N4_2 N -0.8185(3) -0.2652(3) -0.14838(17) 0.0590(8) Uani 1 1 d . . . . .
H4_2 H -0.7831 -0.3343 -0.1251 0.071 Uiso 1 1 calc R U . . .
N5_2 N -1.4687(3) -0.2104(5) -0.5065(2) 0.0676(9) Uani 1 1 d . . . . .
C1_2 C -0.9303(3) -0.2747(4) -0.2114(2) 0.0509(9) Uani 1 1 d . . . . .
C2_2 C -0.9890(4) -0.4058(4) -0.2324(2) 0.0540(10) Uani 1 1 d . . . . .
N3_2 N -0.9229(4) -0.4975(4) -0.1900(2) 0.0826(11) Uani 1 1 d D . . . .
C3A_2 C -0.9557(15) -0.6280(15) -0.2164(10) 0.083(4) Uani 0.599(17) 1 d D U P B
1
H3AA_2 H -0.9284 -0.6880 -0.1748 0.100 Uiso 0.599(17) 1 calc R U P B 1
H3AB_2 H -0.8927 -0.6490 -0.2550 0.100 Uiso 0.599(17) 1 calc R U P B 1
C4A_2 C -1.1367(13) -0.6348(10) -0.2491(8) 0.088(4) Uani 0.599(17) 1 d D U P B
1
H4AA_2 H -1.1986 -0.6094 -0.2108 0.106 Uiso 0.599(17) 1 calc R U P B 1
H4AB_2 H -1.1662 -0.7220 -0.2643 0.106 Uiso 0.599(17) 1 calc R U P B 1
C3B_2 C -1.0678(19) -0.6544(13) -0.2887(10) 0.078(5) Uani 0.401(17) 1 d D U P B
2
H3BA_2 H -0.9720 -0.6560 -0.3118 0.094 Uiso 0.401(17) 1 calc R U P B 2
H3BB_2 H -1.1240 -0.7354 -0.2985 0.094 Uiso 0.401(17) 1 calc R U P B 2
C4B_2 C -1.024(3) -0.629(2) -0.2032(13) 0.077(5) Uani 0.401(17) 1 d . U P B 2
H4BA_2 H -0.9594 -0.6993 -0.1787 0.092 Uiso 0.401(17) 1 calc R U P B 2
H4BB_2 H -1.1208 -0.6224 -0.1815 0.092 Uiso 0.401(17) 1 calc R U P B 2
C5_2 C -1.1762(5) -0.5438(4) -0.3189(3) 0.0715(12) Uani 1 1 d . . . . .
H5AA_2 H -1.1295 -0.5771 -0.3606 0.086 Uiso 0.599(17) 1 calc R U P B 1
H5AB_2 H -1.2920 -0.5374 -0.3352 0.086 Uiso 0.599(17) 1 calc R U P B 1
H5BC_2 H -1.1986 -0.5485 -0.3737 0.086 Uiso 0.401(17) 1 calc R U P B 2
H5BD_2 H -1.2779 -0.5528 -0.3012 0.086 Uiso 0.401(17) 1 calc R U P B 2
N2_2 N -1.1078(3) -0.4160(3) -0.29628(18) 0.0540(8) Uani 1 1 d . . . . .
C6_2 C -1.1667(3) -0.3065(4) -0.33786(19) 0.0486(9) Uani 1 1 d . . . . .
C7_2 C -1.2861(4) -0.3144(4) -0.4023(2) 0.0538(9) Uani 1 1 d . . . . .
H7_2 H -1.3282 -0.3933 -0.4200 0.065 Uiso 1 1 calc R U . . .
C8_2 C -1.3409(3) -0.2015(4) -0.4395(2) 0.0535(9) Uani 1 1 d . . . . .
C9_2 C -1.2809(4) -0.0819(4) -0.4166(2) 0.0592(10) Uani 1 1 d . . . . .
H9_2 H -1.3201 -0.0083 -0.4428 0.071 Uiso 1 1 calc R U . . .
C10_2 C -1.1604(4) -0.0755(4) -0.3532(2) 0.0572(10) Uani 1 1 d . . . . .
H10_2 H -1.1176 0.0039 -0.3370 0.069 Uiso 1 1 calc R U . . .
C11_2 C -1.1014(3) -0.1856(4) -0.31315(19) 0.0488(9) Uani 1 1 d . . . . .
C12_2 C -0.7545(3) -0.1425(4) -0.1176(2) 0.0614(11) Uani 1 1 d . . . . .
H12A_2 H -0.7196 -0.0934 -0.1577 0.074 Uiso 1 1 calc R U . . .
H12B_2 H -0.6606 -0.1581 -0.0789 0.074 Uiso 1 1 calc R U . . .
C13_2 C -0.8727(3) -0.0654(4) -0.0844(2) 0.0551(9) Uani 1 1 d . . . . .
C14_2 C -0.9659(4) 0.0346(4) -0.1100(2) 0.0715(11) Uani 1 1 d . . . . .
H14_2 H -0.9711 0.0749 -0.1566 0.086 Uiso 1 1 calc R U . . .
C15_2 C -1.0557(5) 0.0678(6) -0.0525(3) 0.0910(16) Uani 1 1 d . . . . .
H15_2 H -1.1297 0.1343 -0.0542 0.109 Uiso 1 1 calc R U . . .
C16_2 C -1.0135(6) -0.0139(6) 0.0034(4) 0.0903(16) Uani 1 1 d . . . . .
H16_2 H -1.0547 -0.0144 0.0482 0.108 Uiso 1 1 calc R U . . .


_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_1 N5_1 1.238(5) . ?
O2_1 N5_1 1.211(5) . ?
N1_1 C1_1 1.308(5) . ?
N1_1 C11_1 1.392(4) . ?
N3_1 C3_1 1.468(5) . ?
N3_1 C2_1 1.295(5) . ?
C3_1 H3A_1 0.9700 . ?
C3_1 H3B_1 0.9700 . ?
C3_1 C4_1 1.505(6) . ?
C4_1 H4A_1 0.9700 . ?
C4_1 H4B_1 0.9700 . ?
C4_1 C5_1 1.508(6) . ?
C5_1 H5A_1 0.9700 . ?
C5_1 H5B_1 0.9700 . ?
C5_1 N2_1 1.482(5) . ?
N4_1 H4_1 0.8600 . ?
N4_1 C1_1 1.344(4) . ?
N4_1 C12_1 1.458(5) . ?
N5_1 C8_1 1.475(5) . ?
C1_1 C2_1 1.487(5) . ?
C2_1 N2_1 1.386(4) . ?
N2_1 C6_1 1.398(5) . ?
C6_1 C7_1 1.400(5) . ?
C6_1 C11_1 1.421(5) . ?
C7_1 H7_1 0.9300 . ?
C7_1 C8_1 1.384(6) . ?
C8_1 C9_1 1.382(6) . ?
C9_1 H9_1 0.9300 . ?
C9_1 C10_1 1.378(5) . ?
C10_1 H10_1 0.9300 . ?
C10_1 C11_1 1.400(5) . ?
C12_1 H12A_1 0.9700 . ?
C12_1 H12B_1 0.9700 . ?
C12_1 H12C_1 0.9700 . ?
C12_1 H12D_1 0.9700 . ?
C12_1 C13A_1 1.469(18) . ?
C12_1 C13B_1 1.500(11) . ?
C13A_1 O3A_1 1.36(2) . ?
C13A_1 C14A_1 1.32(2) . ?
O3A_1 C16A_1 1.41(2) . ?
C14A_1 H14A_1 0.9300 . ?
C14A_1 C15A_1 1.38(2) . ?
C15A_1 H15A_1 0.9300 . ?
C15A_1 C16A_1 1.36(3) . ?
C16A_1 H16A_1 0.9300 . ?
C13B_1 O3B_1 1.386(12) . ?
C13B_1 C14B_1 1.355(12) . ?
O3B_1 C16B_1 1.405(12) . ?
C16B_1 H16B_1 0.9300 . ?
C16B_1 C15B_1 1.37(2) . ?
C15B_1 H15B_1 0.9300 . ?
C15B_1 C14B_1 1.379(18) . ?
C14B_1 H14B_1 0.9300 . ?
O1_2 N5_2 1.224(5) . ?
O2_2 N5_2 1.232(5) . ?
O3_2 C13_2 1.368(4) . ?
O3_2 C16_2 1.382(6) . ?
N1_2 C1_2 1.315(5) . ?
N1_2 C11_2 1.392(4) . ?
N4_2 H4_2 0.8600 . ?
N4_2 C1_2 1.342(4) . ?
N4_2 C12_2 1.460(5) . ?
N5_2 C8_2 1.469(5) . ?
C1_2 C2_2 1.481(6) . ?
C2_2 N3_2 1.287(5) . ?
C2_2 N2_2 1.386(5) . ?
N3_2 C3A_2 1.453(15) . ?
N3_2 C4B_2 1.61(2) . ?
C3A_2 H3AA_2 0.9700 . ?
C3A_2 H3AB_2 0.9700 . ?
C3A_2 C4A_2 1.536(16) . ?
C4A_2 H4AA_2 0.9700 . ?
C4A_2 H4AB_2 0.9700 . ?
C4A_2 C5_2 1.561(11) . ?
C3B_2 H3BA_2 0.9700 . ?
C3B_2 H3BB_2 0.9700 . ?
C3B_2 C4B_2 1.54(3) . ?
C3B_2 C5_2 1.512(14) . ?
C4B_2 H4BA_2 0.9700 . ?
C4B_2 H4BB_2 0.9700 . ?
C5_2 H5AA_2 0.9700 . ?
C5_2 H5AB_2 0.9700 . ?
C5_2 H5BC_2 0.9700 . ?
C5_2 H5BD_2 0.9700 . ?
C5_2 N2_2 1.480(5) . ?
N2_2 C6_2 1.407(5) . ?
C6_2 C7_2 1.394(5) . ?
C6_2 C11_2 1.416(5) . ?
C7_2 H7_2 0.9300 . ?
C7_2 C8_2 1.392(5) . ?
C8_2 C9_2 1.382(6) . ?
C9_2 H9_2 0.9300 . ?
C9_2 C10_2 1.386(5) . ?
C10_2 H10_2 0.9300 . ?
C10_2 C11_2 1.399(5) . ?
C12_2 H12A_2 0.9700 . ?
C12_2 H12B_2 0.9700 . ?
C12_2 C13_2 1.485(5) . ?
C13_2 C14_2 1.338(5) . ?
C14_2 H14_2 0.9300 . ?
C14_2 C15_2 1.426(6) . ?
C15_2 H15_2 0.9300 . ?
C15_2 C16_2 1.317(7) . ?
C16_2 H16_2 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1_1 N1_1 C11_1 117.5(3) . . ?
C2_1 N3_1 C3_1 116.9(3) . . ?
N3_1 C3_1 H3A_1 109.3 . . ?
N3_1 C3_1 H3B_1 109.3 . . ?
N3_1 C3_1 C4_1 111.8(4) . . ?
H3A_1 C3_1 H3B_1 107.9 . . ?
C4_1 C3_1 H3A_1 109.3 . . ?
C4_1 C3_1 H3B_1 109.3 . . ?
C3_1 C4_1 H4A_1 109.5 . . ?
C3_1 C4_1 H4B_1 109.5 . . ?
C3_1 C4_1 C5_1 110.5(4) . . ?
H4A_1 C4_1 H4B_1 108.1 . . ?
C5_1 C4_1 H4A_1 109.5 . . ?
C5_1 C4_1 H4B_1 109.5 . . ?
C4_1 C5_1 H5A_1 109.5 . . ?
C4_1 C5_1 H5B_1 109.5 . . ?
H5A_1 C5_1 H5B_1 108.1 . . ?
N2_1 C5_1 C4_1 110.5(3) . . ?
N2_1 C5_1 H5A_1 109.5 . . ?
N2_1 C5_1 H5B_1 109.5 . . ?
C1_1 N4_1 H4_1 118.4 . . ?
C1_1 N4_1 C12_1 123.2(4) . . ?
C12_1 N4_1 H4_1 118.4 . . ?
O1_1 N5_1 C8_1 116.5(5) . . ?
O2_1 N5_1 O1_1 123.5(4) . . ?
O2_1 N5_1 C8_1 120.0(5) . . ?
N1_1 C1_1 N4_1 120.7(4) . . ?
N1_1 C1_1 C2_1 124.8(3) . . ?
N4_1 C1_1 C2_1 114.5(4) . . ?
N3_1 C2_1 C1_1 117.9(3) . . ?
N3_1 C2_1 N2_1 126.7(4) . . ?
N2_1 C2_1 C1_1 115.3(3) . . ?
C2_1 N2_1 C5_1 119.0(3) . . ?
C2_1 N2_1 C6_1 121.3(3) . . ?
C6_1 N2_1 C5_1 119.7(3) . . ?
N2_1 C6_1 C7_1 121.8(3) . . ?
N2_1 C6_1 C11_1 118.4(3) . . ?
C7_1 C6_1 C11_1 119.8(4) . . ?
C6_1 C7_1 H7_1 120.7 . . ?
C8_1 C7_1 C6_1 118.5(4) . . ?
C8_1 C7_1 H7_1 120.7 . . ?
C7_1 C8_1 N5_1 117.5(4) . . ?
C9_1 C8_1 N5_1 119.1(4) . . ?
C9_1 C8_1 C7_1 123.4(3) . . ?
C8_1 C9_1 H9_1 121.3 . . ?
C10_1 C9_1 C8_1 117.5(4) . . ?
C10_1 C9_1 H9_1 121.3 . . ?
C9_1 C10_1 H10_1 118.8 . . ?
C9_1 C10_1 C11_1 122.5(4) . . ?
C11_1 C10_1 H10_1 118.8 . . ?
N1_1 C11_1 C6_1 122.3(3) . . ?
N1_1 C11_1 C10_1 119.4(3) . . ?
C10_1 C11_1 C6_1 118.3(3) . . ?
N4_1 C12_1 H12A_1 108.6 . . ?
N4_1 C12_1 H12B_1 108.6 . . ?
N4_1 C12_1 H12C_1 109.0 . . ?
N4_1 C12_1 H12D_1 109.0 . . ?
N4_1 C12_1 C13A_1 114(2) . . ?
N4_1 C12_1 C13B_1 113.0(12) . . ?
H12A_1 C12_1 H12B_1 107.6 . . ?
H12C_1 C12_1 H12D_1 107.8 . . ?
C13A_1 C12_1 H12A_1 108.6 . . ?
C13A_1 C12_1 H12B_1 108.6 . . ?
C13B_1 C12_1 H12C_1 109.0 . . ?
C13B_1 C12_1 H12D_1 109.0 . . ?
O3A_1 C13A_1 C12_1 119(2) . . ?
C14A_1 C13A_1 C12_1 126(2) . . ?
C14A_1 C13A_1 O3A_1 113.8(17) . . ?
C13A_1 O3A_1 C16A_1 102.7(19) . . ?
C13A_1 C14A_1 H14A_1 127.2 . . ?
C13A_1 C14A_1 C15A_1 105.5(17) . . ?
C15A_1 C14A_1 H14A_1 127.2 . . ?
C14A_1 C15A_1 H15A_1 125.7 . . ?
C16A_1 C15A_1 C14A_1 108.6(18) . . ?
C16A_1 C15A_1 H15A_1 125.7 . . ?
O3A_1 C16A_1 H16A_1 125.7 . . ?
C15A_1 C16A_1 O3A_1 109(2) . . ?
C15A_1 C16A_1 H16A_1 125.7 . . ?
O3B_1 C13B_1 C12_1 115.5(10) . . ?
C14B_1 C13B_1 C12_1 138.2(12) . . ?
C14B_1 C13B_1 O3B_1 106.2(9) . . ?
C13B_1 O3B_1 C16B_1 107.7(9) . . ?
O3B_1 C16B_1 H16B_1 125.7 . . ?
C15B_1 C16B_1 O3B_1 108.6(11) . . ?
C15B_1 C16B_1 H16B_1 125.7 . . ?
C16B_1 C15B_1 H15B_1 127.1 . . ?
C16B_1 C15B_1 C14B_1 105.9(12) . . ?
C14B_1 C15B_1 H15B_1 127.1 . . ?
C13B_1 C14B_1 C15B_1 111.6(12) . . ?
C13B_1 C14B_1 H14B_1 124.2 . . ?
C15B_1 C14B_1 H14B_1 124.2 . . ?
C13_2 O3_2 C16_2 106.3(4) . . ?
C1_2 N1_2 C11_2 117.3(3) . . ?
C1_2 N4_2 H4_2 118.6 . . ?
C1_2 N4_2 C12_2 122.8(3) . . ?
C12_2 N4_2 H4_2 118.6 . . ?
O1_2 N5_2 O2_2 122.3(3) . . ?
O1_2 N5_2 C8_2 118.2(4) . . ?
O2_2 N5_2 C8_2 119.5(4) . . ?
N1_2 C1_2 N4_2 119.7(4) . . ?
N1_2 C1_2 C2_2 124.5(3) . . ?
N4_2 C1_2 C2_2 115.9(4) . . ?
N3_2 C2_2 C1_2 116.5(3) . . ?
N3_2 C2_2 N2_2 127.3(4) . . ?
N2_2 C2_2 C1_2 116.2(4) . . ?
C2_2 N3_2 C3A_2 117.8(7) . . ?
C2_2 N3_2 C4B_2 112.7(9) . . ?
N3_2 C3A_2 H3AA_2 110.4 . . ?
N3_2 C3A_2 H3AB_2 110.4 . . ?
N3_2 C3A_2 C4A_2 106.7(11) . . ?
H3AA_2 C3A_2 H3AB_2 108.6 . . ?
C4A_2 C3A_2 H3AA_2 110.4 . . ?
C4A_2 C3A_2 H3AB_2 110.4 . . ?
C3A_2 C4A_2 H4AA_2 109.8 . . ?
C3A_2 C4A_2 H4AB_2 109.8 . . ?
C3A_2 C4A_2 C5_2 109.6(11) . . ?
H4AA_2 C4A_2 H4AB_2 108.2 . . ?
C5_2 C4A_2 H4AA_2 109.8 . . ?
C5_2 C4A_2 H4AB_2 109.8 . . ?
H3BA_2 C3B_2 H3BB_2 108.9 . . ?
C4B_2 C3B_2 H3BA_2 110.8 . . ?
C4B_2 C3B_2 H3BB_2 110.8 . . ?
C5_2 C3B_2 H3BA_2 110.8 . . ?
C5_2 C3B_2 H3BB_2 110.8 . . ?
C5_2 C3B_2 C4B_2 104.5(16) . . ?
N3_2 C4B_2 H4BA_2 109.9 . . ?
N3_2 C4B_2 H4BB_2 109.9 . . ?
C3B_2 C4B_2 N3_2 108.8(15) . . ?
C3B_2 C4B_2 H4BA_2 109.9 . . ?
C3B_2 C4B_2 H4BB_2 109.9 . . ?
H4BA_2 C4B_2 H4BB_2 108.3 . . ?
C4A_2 C5_2 H5AA_2 110.1 . . ?
C4A_2 C5_2 H5AB_2 110.1 . . ?
C3B_2 C5_2 H5BC_2 108.7 . . ?
C3B_2 C5_2 H5BD_2 108.7 . . ?
H5AA_2 C5_2 H5AB_2 108.4 . . ?
H5BC_2 C5_2 H5BD_2 107.6 . . ?
N2_2 C5_2 C4A_2 108.1(5) . . ?
N2_2 C5_2 C3B_2 114.1(5) . . ?
N2_2 C5_2 H5AA_2 110.1 . . ?
N2_2 C5_2 H5AB_2 110.1 . . ?
N2_2 C5_2 H5BC_2 108.7 . . ?
N2_2 C5_2 H5BD_2 108.7 . . ?
C2_2 N2_2 C5_2 119.1(3) . . ?
C2_2 N2_2 C6_2 120.7(3) . . ?
C6_2 N2_2 C5_2 120.2(3) . . ?
N2_2 C6_2 C11_2 118.5(3) . . ?
C7_2 C6_2 N2_2 121.8(3) . . ?
C7_2 C6_2 C11_2 119.7(4) . . ?
C6_2 C7_2 H7_2 120.8 . . ?
C8_2 C7_2 C6_2 118.5(4) . . ?
C8_2 C7_2 H7_2 120.8 . . ?
C7_2 C8_2 N5_2 118.2(4) . . ?
C9_2 C8_2 N5_2 118.5(4) . . ?
C9_2 C8_2 C7_2 123.3(3) . . ?
C8_2 C9_2 H9_2 121.2 . . ?
C8_2 C9_2 C10_2 117.6(4) . . ?
C10_2 C9_2 H9_2 121.2 . . ?
C9_2 C10_2 H10_2 119.2 . . ?
C9_2 C10_2 C11_2 121.7(4) . . ?
C11_2 C10_2 H10_2 119.2 . . ?
N1_2 C11_2 C6_2 122.8(3) . . ?
N1_2 C11_2 C10_2 118.0(3) . . ?
C10_2 C11_2 C6_2 119.2(3) . . ?
N4_2 C12_2 H12A_2 108.9 . . ?
N4_2 C12_2 H12B_2 108.9 . . ?
N4_2 C12_2 C13_2 113.4(2) . . ?
H12A_2 C12_2 H12B_2 107.7 . . ?
C13_2 C12_2 H12A_2 108.9 . . ?
C13_2 C12_2 H12B_2 108.9 . . ?
O3_2 C13_2 C12_2 117.8(3) . . ?
C14_2 C13_2 O3_2 109.4(3) . . ?
C14_2 C13_2 C12_2 132.8(4) . . ?
C13_2 C14_2 H14_2 126.4 . . ?
C13_2 C14_2 C15_2 107.2(4) . . ?
C15_2 C14_2 H14_2 126.4 . . ?
C14_2 C15_2 H15_2 126.6 . . ?
C16_2 C15_2 C14_2 106.8(5) . . ?
C16_2 C15_2 H15_2 126.6 . . ?
O3_2 C16_2 H16_2 124.9 . . ?
C15_2 C16_2 O3_2 110.3(4) . . ?
C15_2 C16_2 H16_2 124.9 . . ?

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
O1_1 N5_1 C8_1 C7_1 -163.2(3) . . . . ?
O1_1 N5_1 C8_1 C9_1 16.2(5) . . . . ?
O2_1 N5_1 C8_1 C7_1 15.5(5) . . . . ?
O2_1 N5_1 C8_1 C9_1 -165.1(4) . . . . ?
N1_1 C1_1 C2_1 N3_1 -178.0(3) . . . . ?
N1_1 C1_1 C2_1 N2_1 3.0(4) . . . . ?
N3_1 C3_1 C4_1 C5_1 -56.5(5) . . . . ?
N3_1 C2_1 N2_1 C5_1 -7.1(5) . . . . ?
N3_1 C2_1 N2_1 C6_1 174.5(3) . . . . ?
C3_1 N3_1 C2_1 C1_1 -179.6(3) . . . . ?
C3_1 N3_1 C2_1 N2_1 -0.7(5) . . . . ?
C3_1 C4_1 C5_1 N2_1 47.8(5) . . . . ?
C4_1 C5_1 N2_1 C2_1 -17.9(4) . . . . ?
C4_1 C5_1 N2_1 C6_1 160.5(3) . . . . ?
C5_1 N2_1 C6_1 C7_1 6.8(4) . . . . ?
C5_1 N2_1 C6_1 C11_1 -172.8(3) . . . . ?
N4_1 C1_1 C2_1 N3_1 2.8(4) . . . . ?
N4_1 C1_1 C2_1 N2_1 -176.3(3) . . . . ?
N4_1 C12_1 C13A_1 O3A_1 -74(4) . . . . ?
N4_1 C12_1 C13A_1 C14A_1 97(5) . . . . ?
N4_1 C12_1 C13B_1 O3B_1 -75(2) . . . . ?
N4_1 C12_1 C13B_1 C14B_1 108(3) . . . . ?
N5_1 C8_1 C9_1 C10_1 -179.1(3) . . . . ?
C1_1 N1_1 C11_1 C6_1 -2.9(4) . . . . ?
C1_1 N1_1 C11_1 C10_1 178.1(3) . . . . ?
C1_1 N4_1 C12_1 C13A_1 -78.8(14) . . . . ?
C1_1 N4_1 C12_1 C13B_1 -89.2(8) . . . . ?
C1_1 C2_1 N2_1 C5_1 171.8(2) . . . . ?
C1_1 C2_1 N2_1 C6_1 -6.5(4) . . . . ?
C2_1 N3_1 C3_1 C4_1 32.8(5) . . . . ?
C2_1 N2_1 C6_1 C7_1 -174.9(3) . . . . ?
C2_1 N2_1 C6_1 C11_1 5.5(4) . . . . ?
N2_1 C6_1 C7_1 C8_1 -177.1(3) . . . . ?
N2_1 C6_1 C11_1 N1_1 -0.6(4) . . . . ?
N2_1 C6_1 C11_1 C10_1 178.4(3) . . . . ?
C6_1 C7_1 C8_1 N5_1 177.3(3) . . . . ?
C6_1 C7_1 C8_1 C9_1 -2.1(5) . . . . ?
C7_1 C6_1 C11_1 N1_1 179.8(3) . . . . ?
C7_1 C6_1 C11_1 C10_1 -1.2(4) . . . . ?
C7_1 C8_1 C9_1 C10_1 0.3(5) . . . . ?
C8_1 C9_1 C10_1 C11_1 1.1(6) . . . . ?
C9_1 C10_1 C11_1 N1_1 178.4(3) . . . . ?
C9_1 C10_1 C11_1 C6_1 -0.7(5) . . . . ?
C11_1 N1_1 C1_1 N4_1 -179.1(3) . . . . ?
C11_1 N1_1 C1_1 C2_1 1.7(4) . . . . ?
C11_1 C6_1 C7_1 C8_1 2.5(4) . . . . ?
C12_1 N4_1 C1_1 N1_1 -4.9(5) . . . . ?
C12_1 N4_1 C1_1 C2_1 174.4(3) . . . . ?
C12_1 C13A_1 O3A_1 C16A_1 -180(4) . . . . ?
C12_1 C13A_1 C14A_1 C15A_1 -179(4) . . . . ?
C12_1 C13B_1 O3B_1 C16B_1 -179.8(18) . . . . ?
C12_1 C13B_1 C14B_1 C15B_1 179(3) . . . . ?
C13A_1 O3A_1 C16A_1 C15A_1 -5(4) . . . . ?
C13A_1 C14A_1 C15A_1 C16A_1 4(3) . . . . ?
O3A_1 C13A_1 C14A_1 C15A_1 -8(4) . . . . ?
C14A_1 C13A_1 O3A_1 C16A_1 9(5) . . . . ?
C14A_1 C15A_1 C16A_1 O3A_1 1(3) . . . . ?
C13B_1 O3B_1 C16B_1 C15B_1 1.4(17) . . . . ?
O3B_1 C13B_1 C14B_1 C15B_1 3(2) . . . . ?
O3B_1 C16B_1 C15B_1 C14B_1 0.2(14) . . . . ?
C16B_1 C15B_1 C14B_1 C13B_1 -1.9(19) . . . . ?
C14B_1 C13B_1 O3B_1 C16B_1 -2(2) . . . . ?
O1_2 N5_2 C8_2 C7_2 172.6(3) . . . . ?
O1_2 N5_2 C8_2 C9_2 -7.5(5) . . . . ?
O2_2 N5_2 C8_2 C7_2 -4.8(5) . . . . ?
O2_2 N5_2 C8_2 C9_2 175.1(3) . . . . ?
O3_2 C13_2 C14_2 C15_2 0.6(4) . . . . ?
N1_2 C1_2 C2_2 N3_2 178.0(3) . . . . ?
N1_2 C1_2 C2_2 N2_2 -1.3(5) . . . . ?
N4_2 C1_2 C2_2 N3_2 -2.5(4) . . . . ?
N4_2 C1_2 C2_2 N2_2 178.2(2) . . . . ?
N4_2 C12_2 C13_2 O3_2 78.1(4) . . . . ?
N4_2 C12_2 C13_2 C14_2 -101.0(5) . . . . ?
N5_2 C8_2 C9_2 C10_2 -180.0(3) . . . . ?
C1_2 N1_2 C11_2 C6_2 -1.2(4) . . . . ?
C1_2 N1_2 C11_2 C10_2 178.1(3) . . . . ?
C1_2 N4_2 C12_2 C13_2 70.5(4) . . . . ?
C1_2 C2_2 N3_2 C3A_2 -169.0(7) . . . . ?
C1_2 C2_2 N3_2 C4B_2 165.0(9) . . . . ?
C1_2 C2_2 N2_2 C5_2 -177.8(3) . . . . ?
C1_2 C2_2 N2_2 C6_2 0.3(4) . . . . ?
C2_2 N3_2 C3A_2 C4A_2 -42.8(15) . . . . ?
C2_2 N3_2 C4B_2 C3B_2 47.4(19) . . . . ?
C2_2 N2_2 C6_2 C7_2 180.0(3) . . . . ?
C2_2 N2_2 C6_2 C11_2 0.2(4) . . . . ?
N3_2 C2_2 N2_2 C5_2 3.0(6) . . . . ?
N3_2 C2_2 N2_2 C6_2 -179.0(3) . . . . ?
N3_2 C3A_2 C4A_2 C5_2 63.5(17) . . . . ?
C3A_2 C4A_2 C5_2 N2_2 -51.1(13) . . . . ?
C4A_2 C5_2 N2_2 C2_2 18.6(7) . . . . ?
C4A_2 C5_2 N2_2 C6_2 -159.5(6) . . . . ?
C3B_2 C5_2 N2_2 C2_2 -22.4(10) . . . . ?
C3B_2 C5_2 N2_2 C6_2 159.6(9) . . . . ?
C4B_2 C3B_2 C5_2 N2_2 51.9(16) . . . . ?
C5_2 C3B_2 C4B_2 N3_2 -63(2) . . . . ?
C5_2 N2_2 C6_2 C7_2 -2.0(5) . . . . ?
C5_2 N2_2 C6_2 C11_2 178.2(3) . . . . ?
N2_2 C2_2 N3_2 C3A_2 10.2(9) . . . . ?
N2_2 C2_2 N3_2 C4B_2 -15.8(10) . . . . ?
N2_2 C6_2 C7_2 C8_2 178.5(3) . . . . ?
N2_2 C6_2 C11_2 N1_2 0.3(4) . . . . ?
N2_2 C6_2 C11_2 C10_2 -179.0(3) . . . . ?
C6_2 C7_2 C8_2 N5_2 -178.9(3) . . . . ?
C6_2 C7_2 C8_2 C9_2 1.2(5) . . . . ?
C7_2 C6_2 C11_2 N1_2 -179.5(3) . . . . ?
C7_2 C6_2 C11_2 C10_2 1.2(4) . . . . ?
C7_2 C8_2 C9_2 C10_2 -0.1(5) . . . . ?
C8_2 C9_2 C10_2 C11_2 -0.4(5) . . . . ?
C9_2 C10_2 C11_2 N1_2 -179.4(3) . . . . ?
C9_2 C10_2 C11_2 C6_2 -0.1(5) . . . . ?
C11_2 N1_2 C1_2 N4_2 -177.8(2) . . . . ?
C11_2 N1_2 C1_2 C2_2 1.7(4) . . . . ?
C11_2 C6_2 C7_2 C8_2 -1.7(4) . . . . ?
C12_2 N4_2 C1_2 N1_2 2.9(4) . . . . ?
C12_2 N4_2 C1_2 C2_2 -176.6(3) . . . . ?
C12_2 C13_2 C14_2 C15_2 179.8(4) . . . . ?
C13_2 O3_2 C16_2 C15_2 -0.2(5) . . . . ?
C13_2 C14_2 C15_2 C16_2 -0.7(5) . . . . ?
C14_2 C15_2 C16_2 O3_2 0.6(5) . . . . ?
C16_2 O3_2 C13_2 C12_2 -179.6(3) . . . . ?
C16_2 O3_2 C13_2 C14_2 -0.3(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform, methanol'
_exptl_crystal_preparation       Luminescent
