# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003

data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'David H. Reid'
'Jan C. A. Boeyens'
'Leanne M. Cook'
'Yunxiang Ding'
'Manuel A. Fernandes'

_publ_contact_author_name        'Prof David H. Reid'
_publ_contact_author_address     
;
School of Chemistry
University of the Witwatersrand
PO WITS
Johannesburg
Gauteng
2050
SOUTH AFRICA
;

_publ_contact_author_email       MANUEL@HOBBES.GH.WITS.AC.ZA

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
Thermal oligomerisation of aryl isocyanides:
formation of pyrazino[1,2-a:4,5-a"S]diindoles and indigo diarylimines
;

####################################################################

data_mrd3_s
_database_code_CSD               205332

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
? 
;
_chemical_name_common            
;
5,5'-difluorophenylindigo--3,3'-bis(4-fluorophenylimine)
;
_chemical_melting_point          '>270 \%C'
_chemical_formula_moiety         'C28 H16 F4 N4'
_chemical_formula_sum            'C28 H16 F4 N4'
_chemical_formula_weight         484.45

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'
F F 0.0171 0.0103 '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
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6207(11)
_cell_length_b                   10.9214(13)
_cell_length_c                   11.3237(13)
_cell_angle_alpha                109.183(2)
_cell_angle_beta                 101.783(2)
_cell_angle_gamma                98.254(2)
_cell_volume                     1071.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9674
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_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  '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            6401
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         25.99
_reflns_number_total             4160
_reflns_number_gt                2227
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 F^2^ against ALL reflections.  The weighted R-factor wR and 
goodness of fit S are based on F^2^, conventional R-factors R are based 
on F, with F set to zero for negative F^2^. The threshold expression of 
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
not relevant to the choice of reflections for refinement.  R-factors based 
on F^2^ 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/[\s^2^(Fo^2^)+(0.0702P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4160
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1471
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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
F1 F 0.14251(16) 0.03003(15) 0.36627(16) 0.0676(5) Uani 1 1 d . . .
F2 F 0.5653(2) 0.1721(2) 1.00907(17) 0.0932(7) Uani 1 1 d . . .
F1' F 1.31040(17) 0.95699(16) 0.59861(16) 0.0685(5) Uani 1 1 d . . .
F2' F 0.9970(2) 0.83721(18) 0.01138(16) 0.0809(6) Uani 1 1 d . . .
N1 N 0.5769(2) 0.3865(2) 0.33757(19) 0.0436(5) Uani 1 1 d . . .
H1 H 0.5913 0.4112 0.2755 0.052 Uiso 1 1 calc R . .
N2 N 0.6691(2) 0.4089(2) 0.66528(19) 0.0489(6) Uani 1 1 d . . .
H2 H 0.7366 0.4809 0.7006 0.059 Uiso 1 1 calc R . .
N1' N 0.8836(2) 0.5824(2) 0.62435(19) 0.0426(5) Uani 1 1 d . . .
N2' N 0.7831(2) 0.5785(2) 0.30429(19) 0.0441(6) Uani 1 1 d . . .
C2 C 0.6675(3) 0.4368(2) 0.4629(2) 0.0404(6) Uani 1 1 d . . .
C3 C 0.6074(3) 0.3725(2) 0.5354(2) 0.0386(6) Uani 1 1 d . . .
C4 C 0.3639(3) 0.1892(2) 0.4628(3) 0.0441(6) Uani 1 1 d . . .
H4 H 0.3679 0.1784 0.5414 0.053 Uiso 1 1 calc R . .
C5 C 0.2508(3) 0.1189(3) 0.3565(3) 0.0469(7) Uani 1 1 d . . .
C6 C 0.2377(3) 0.1311(3) 0.2368(3) 0.0513(7) Uani 1 1 d . . .
H6 H 0.1575 0.0801 0.1674 0.062 Uiso 1 1 calc R . .
C7 C 0.3427(3) 0.2180(3) 0.2215(3) 0.0493(7) Uani 1 1 d . . .
H7 H 0.3353 0.2279 0.1420 0.059 Uiso 1 1 calc R . .
C8 C 0.6375(3) 0.3450(2) 0.7488(2) 0.0389(6) Uani 1 1 d . . .
C9 C 0.6397(3) 0.4234(3) 0.8741(2) 0.0517(7) Uani 1 1 d . . .
H9 H 0.6569 0.5154 0.8990 0.062 Uiso 1 1 calc R . .
C10 C 0.6165(3) 0.3650(3) 0.9614(3) 0.0585(8) Uani 1 1 d . . .
H10 H 0.6185 0.4171 1.0455 0.070 Uiso 1 1 calc R . .
C11 C 0.5906(3) 0.2298(3) 0.9230(3) 0.0576(8) Uani 1 1 d . . .
C12 C 0.5897(3) 0.1499(3) 0.8011(3) 0.0501(7) Uani 1 1 d . . .
H12 H 0.5729 0.0580 0.7773 0.060 Uiso 1 1 calc R . .
C13 C 0.6143(3) 0.2086(3) 0.7138(2) 0.0451(7) Uani 1 1 d . . .
H13 H 0.6152 0.1558 0.6308 0.054 Uiso 1 1 calc R . .
C2' C 0.7968(3) 0.5366(2) 0.5049(2) 0.0390(6) Uani 1 1 d . . .
C3' C 0.8517(2) 0.6052(2) 0.4225(2) 0.0376(6) Uani 1 1 d . . .
C4' C 1.0907(3) 0.7943(2) 0.5000(2) 0.0438(6) Uani 1 1 d . . .
H4' H 1.0825 0.8099 0.4232 0.053 Uiso 1 1 calc R . .
C5' C 1.2056(3) 0.8638(2) 0.6075(3) 0.0464(7) Uani 1 1 d . . .
C6' C 1.2220(3) 0.8469(3) 0.7240(3) 0.0485(7) Uani 1 1 d . . .
H6' H 1.3020 0.8972 0.7939 0.058 Uiso 1 1 calc R . .
C7' C 1.1169(3) 0.7533(3) 0.7357(2) 0.0485(7) Uani 1 1 d . . .
H7' H 1.1254 0.7397 0.8135 0.058 Uiso 1 1 calc R . .
C8' C 0.8418(3) 0.6478(3) 0.2318(2) 0.0409(6) Uani 1 1 d . . .
C9' C 0.7807(3) 0.7464(3) 0.2072(2) 0.0543(7) Uani 1 1 d . . .
H9' H 0.7037 0.7699 0.2408 0.065 Uiso 1 1 calc R . .
C10' C 0.8327(3) 0.8106(3) 0.1332(3) 0.0588(8) Uani 1 1 d . . .
H10' H 0.7921 0.8778 0.1171 0.071 Uiso 1 1 calc R . .
C11' C 0.9445(3) 0.7737(3) 0.0844(2) 0.0515(7) Uani 1 1 d . . .
C12' C 1.0055(3) 0.6752(3) 0.1040(3) 0.0550(8) Uani 1 1 d . . .
H12' H 1.0808 0.6511 0.0680 0.066 Uiso 1 1 calc R . .
C13' C 0.9534(3) 0.6111(3) 0.1789(3) 0.0522(7) Uani 1 1 d . . .
H13' H 0.9938 0.5432 0.1934 0.063 Uiso 1 1 calc R . .
C3A C 0.4748(3) 0.2789(2) 0.4500(2) 0.0385(6) Uani 1 1 d . . .
C7A C 0.4614(3) 0.2918(2) 0.3278(2) 0.0399(6) Uani 1 1 d . . .
C3A' C 0.9878(2) 0.6998(2) 0.5116(2) 0.0385(6) Uani 1 1 d . . .
C7A' C 0.9998(3) 0.6811(2) 0.6298(2) 0.0395(6) 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
F1 0.0510(10) 0.0604(11) 0.0838(12) 0.0303(9) 0.0110(9) -0.0093(8)
F2 0.0952(14) 0.1265(18) 0.0755(12) 0.0694(13) 0.0219(11) 0.0037(12)
F1' 0.0568(10) 0.0618(11) 0.0729(11) 0.0257(9) 0.0071(8) -0.0164(8)
F2' 0.0966(14) 0.0871(13) 0.0699(12) 0.0468(11) 0.0296(10) 0.0008(10)
N1 0.0432(12) 0.0498(13) 0.0374(12) 0.0205(11) 0.0078(10) 0.0034(11)
N2 0.0518(14) 0.0440(13) 0.0398(13) 0.0149(11) 0.0014(11) -0.0059(11)
N1' 0.0421(12) 0.0440(13) 0.0391(13) 0.0158(10) 0.0081(10) 0.0048(10)
N2' 0.0439(12) 0.0485(13) 0.0397(13) 0.0202(11) 0.0092(10) 0.0038(10)
C2 0.0397(14) 0.0413(15) 0.0364(15) 0.0140(12) 0.0063(12) 0.0042(12)
C3 0.0390(14) 0.0376(14) 0.0397(15) 0.0159(12) 0.0103(12) 0.0068(12)
C4 0.0421(15) 0.0431(15) 0.0478(16) 0.0190(13) 0.0121(13) 0.0066(13)
C5 0.0407(15) 0.0374(15) 0.0576(18) 0.0164(14) 0.0108(14) -0.0001(13)
C6 0.0404(16) 0.0486(17) 0.0522(17) 0.0158(14) -0.0025(13) -0.0004(13)
C7 0.0470(16) 0.0511(17) 0.0448(16) 0.0188(13) 0.0050(13) 0.0039(14)
C8 0.0379(14) 0.0411(15) 0.0358(14) 0.0172(12) 0.0057(11) 0.0019(12)
C9 0.0518(17) 0.0515(17) 0.0437(16) 0.0112(14) 0.0100(13) 0.0060(14)
C10 0.0538(18) 0.074(2) 0.0366(16) 0.0128(15) 0.0129(13) -0.0005(16)
C11 0.0476(17) 0.082(2) 0.0506(18) 0.0415(18) 0.0093(14) 0.0009(16)
C12 0.0433(15) 0.0508(17) 0.0575(18) 0.0268(15) 0.0078(14) 0.0073(13)
C13 0.0449(15) 0.0466(16) 0.0407(15) 0.0150(13) 0.0100(12) 0.0059(13)
C2' 0.0391(14) 0.0357(14) 0.0431(15) 0.0159(12) 0.0108(12) 0.0087(12)
C3' 0.0348(14) 0.0353(14) 0.0440(15) 0.0162(12) 0.0114(12) 0.0069(11)
C4' 0.0443(15) 0.0423(15) 0.0453(15) 0.0196(13) 0.0101(13) 0.0059(13)
C5' 0.0424(15) 0.0361(15) 0.0548(17) 0.0154(13) 0.0108(14) -0.0019(12)
C6' 0.0428(15) 0.0433(16) 0.0458(16) 0.0091(13) 0.0031(13) -0.0019(13)
C7' 0.0496(16) 0.0493(17) 0.0425(16) 0.0166(13) 0.0060(13) 0.0088(14)
C8' 0.0377(14) 0.0442(15) 0.0335(14) 0.0127(12) 0.0032(12) 0.0000(12)
C9' 0.0650(19) 0.0588(19) 0.0483(17) 0.0234(15) 0.0210(15) 0.0252(16)
C10' 0.082(2) 0.0540(19) 0.0523(18) 0.0294(16) 0.0208(17) 0.0253(17)
C11' 0.0594(18) 0.0528(18) 0.0387(16) 0.0218(14) 0.0097(14) -0.0054(15)
C12' 0.0423(16) 0.070(2) 0.0534(18) 0.0253(16) 0.0132(14) 0.0087(15)
C13' 0.0458(16) 0.0575(18) 0.0593(18) 0.0305(15) 0.0121(14) 0.0120(14)
C3A 0.0380(14) 0.0362(14) 0.0417(15) 0.0156(12) 0.0106(12) 0.0074(12)
C7A 0.0391(14) 0.0378(14) 0.0434(15) 0.0171(12) 0.0105(12) 0.0067(12)
C3A' 0.0376(14) 0.0354(14) 0.0417(15) 0.0138(12) 0.0105(12) 0.0070(12)
C7A' 0.0375(14) 0.0376(14) 0.0409(15) 0.0123(12) 0.0103(12) 0.0062(12)

_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
F1 C5 1.367(3) . ?
F2 C11 1.365(3) . ?
F1' C5' 1.370(3) . ?
F2' C11' 1.367(3) . ?
N1 C7A 1.364(3) . ?
N1 C2 1.386(3) . ?
N1 H1 0.8600 . ?
N2 C3 1.365(3) . ?
N2 C8 1.402(3) . ?
N2 H2 0.8600 . ?
N1' C2' 1.323(3) . ?
N1' C7A' 1.413(3) . ?
N2' C3' 1.281(3) . ?
N2' C8' 1.428(3) . ?
C2 C3 1.400(3) . ?
C2 C2' 1.411(3) . ?
C3 C3A 1.442(3) . ?
C4 C5 1.356(3) . ?
C4 C3A 1.405(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(4) . ?
C6 C7 1.363(3) . ?
C6 H6 0.9300 . ?
C7 C7A 1.393(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.381(3) . ?
C8 C9 1.389(3) . ?
C9 C10 1.378(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(4) . ?
C12 C13 1.382(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C2' C3' 1.503(3) . ?
C3' C3A' 1.479(3) . ?
C4' C5' 1.372(3) . ?
C4' C3A' 1.382(3) . ?
C4' H4' 0.9300 . ?
C5' C6' 1.372(3) . ?
C6' C7' 1.390(3) . ?
C6' H6' 0.9300 . ?
C7' C7A' 1.379(3) . ?
C7' H7' 0.9300 . ?
C8' C9' 1.376(3) . ?
C8' C13' 1.379(4) . ?
C9' C10' 1.379(4) . ?
C9' H9' 0.9300 . ?
C10' C11' 1.359(4) . ?
C10' H10' 0.9300 . ?
C11' C12' 1.355(4) . ?
C12' C13' 1.387(3) . ?
C12' H12' 0.9300 . ?
C13' H13' 0.9300 . ?
C3A C7A 1.418(3) . ?
C3A' C7A' 1.404(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
C7A N1 C2 109.5(2) . . ?
C7A N1 H1 125.2 . . ?
C2 N1 H1 125.2 . . ?
C3 N2 C8 128.8(2) . . ?
C3 N2 H2 115.6 . . ?
C8 N2 H2 115.6 . . ?
C2' N1' C7A' 106.7(2) . . ?
C3' N2' C8' 119.5(2) . . ?
N1 C2 C3 108.3(2) . . ?
N1 C2 C2' 123.7(2) . . ?
C3 C2 C2' 128.0(2) . . ?
N2 C3 C2 121.0(2) . . ?
N2 C3 C3A 131.5(2) . . ?
C2 C3 C3A 107.3(2) . . ?
C5 C4 C3A 117.7(2) . . ?
C5 C4 H4 121.1 . . ?
C3A C4 H4 121.1 . . ?
C4 C5 F1 118.8(2) . . ?
C4 C5 C6 124.0(2) . . ?
F1 C5 C6 117.2(2) . . ?
C7 C6 C5 119.7(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C7A 118.2(2) . . ?
C6 C7 H7 120.9 . . ?
C7A C7 H7 120.9 . . ?
C13 C8 C9 119.2(2) . . ?
C13 C8 N2 122.4(2) . . ?
C9 C8 N2 118.2(2) . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 119.2(3) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 F2 119.0(3) . . ?
C10 C11 C12 122.2(2) . . ?
F2 C11 C12 118.8(3) . . ?
C11 C12 C13 118.6(3) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C8 C13 C12 120.6(3) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
N1' C2' C2 123.1(2) . . ?
N1' C2' C3' 111.9(2) . . ?
C2 C2' C3' 125.0(2) . . ?
N2' C3' C3A' 134.1(2) . . ?
N2' C3' C2' 122.5(2) . . ?
C3A' C3' C2' 103.4(2) . . ?
C5' C4' C3A' 116.7(2) . . ?
C5' C4' H4' 121.7 . . ?
C3A' C4' H4' 121.7 . . ?
F1' C5' C4' 118.0(2) . . ?
F1' C5' C6' 117.7(2) . . ?
C4' C5' C6' 124.2(2) . . ?
C5' C6' C7' 118.8(2) . . ?
C5' C6' H6' 120.6 . . ?
C7' C6' H6' 120.6 . . ?
C7A' C7' C6' 118.8(2) . . ?
C7A' C7' H7' 120.6 . . ?
C6' C7' H7' 120.6 . . ?
C9' C8' C13' 119.4(2) . . ?
C9' C8' N2' 120.0(2) . . ?
C13' C8' N2' 120.5(2) . . ?
C8' C9' C10' 120.6(3) . . ?
C8' C9' H9' 119.7 . . ?
C10' C9' H9' 119.7 . . ?
C11' C10' C9' 118.5(3) . . ?
C11' C10' H10' 120.7 . . ?
C9' C10' H10' 120.7 . . ?
C12' C11' C10' 122.7(2) . . ?
C12' C11' F2' 118.4(3) . . ?
C10' C11' F2' 118.9(3) . . ?
C11' C12' C13' 118.7(3) . . ?
C11' C12' H12' 120.7 . . ?
C13' C12' H12' 120.7 . . ?
C8' C13' C12' 120.1(3) . . ?
C8' C13' H13' 120.0 . . ?
C12' C13' H13' 120.0 . . ?
C4 C3A C7A 118.4(2) . . ?
C4 C3A C3 135.7(2) . . ?
C7A C3A C3 105.9(2) . . ?
N1 C7A C7 129.1(2) . . ?
N1 C7A C3A 109.0(2) . . ?
C7 C7A C3A 121.9(2) . . ?
C4' C3A' C7A' 120.7(2) . . ?
C4' C3A' C3' 134.1(2) . . ?
C7A' C3A' C3' 105.2(2) . . ?
C7' C7A' C3A' 120.8(2) . . ?
C7' C7A' N1' 126.4(2) . . ?
C3A' C7A' N1' 112.9(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
C7A N1 C2 C3 -0.3(3) . . . . ?
C7A N1 C2 C2' -179.9(2) . . . . ?
C8 N2 C3 C2 -170.1(2) . . . . ?
C8 N2 C3 C3A 15.4(5) . . . . ?
N1 C2 C3 N2 -175.6(2) . . . . ?
C2' C2 C3 N2 4.1(4) . . . . ?
N1 C2 C3 C3A 0.2(3) . . . . ?
C2' C2 C3 C3A 179.8(2) . . . . ?
C3A C4 C5 F1 179.3(2) . . . . ?
C3A C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
F1 C5 C6 C7 -179.8(2) . . . . ?
C5 C6 C7 C7A 0.4(4) . . . . ?
C3 N2 C8 C13 42.5(4) . . . . ?
C3 N2 C8 C9 -141.9(3) . . . . ?
C13 C8 C9 C10 -1.1(4) . . . . ?
N2 C8 C9 C10 -176.7(2) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C10 C11 F2 -179.0(2) . . . . ?
C9 C10 C11 C12 1.4(4) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
F2 C11 C12 C13 179.5(2) . . . . ?
C9 C8 C13 C12 1.7(4) . . . . ?
N2 C8 C13 C12 177.1(2) . . . . ?
C11 C12 C13 C8 -0.8(4) . . . . ?
C7A' N1' C2' C2 -179.5(2) . . . . ?
C7A' N1' C2' C3' -0.4(3) . . . . ?
N1 C2 C2' N1' -178.9(2) . . . . ?
C3 C2 C2' N1' 1.5(4) . . . . ?
N1 C2 C2' C3' 2.2(4) . . . . ?
C3 C2 C2' C3' -177.5(2) . . . . ?
C8' N2' C3' C3A' 1.3(4) . . . . ?
C8' N2' C3' C2' 179.9(2) . . . . ?
N1' C2' C3' N2' -178.5(2) . . . . ?
C2 C2' C3' N2' 0.5(4) . . . . ?
N1' C2' C3' C3A' 0.5(3) . . . . ?
C2 C2' C3' C3A' 179.6(2) . . . . ?
C3A' C4' C5' F1' 179.2(2) . . . . ?
C3A' C4' C5' C6' -1.3(4) . . . . ?
F1' C5' C6' C7' 179.8(2) . . . . ?
C4' C5' C6' C7' 0.3(4) . . . . ?
C5' C6' C7' C7A' -0.1(4) . . . . ?
C3' N2' C8' C9' -104.9(3) . . . . ?
C3' N2' C8' C13' 79.3(3) . . . . ?
C13' C8' C9' C10' -1.7(4) . . . . ?
N2' C8' C9' C10' -177.5(2) . . . . ?
C8' C9' C10' C11' 0.5(4) . . . . ?
C9' C10' C11' C12' 0.9(4) . . . . ?
C9' C10' C11' F2' -179.8(2) . . . . ?
C10' C11' C12' C13' -1.2(4) . . . . ?
F2' C11' C12' C13' 179.5(2) . . . . ?
C9' C8' C13' C12' 1.4(4) . . . . ?
N2' C8' C13' C12' 177.3(2) . . . . ?
C11' C12' C13' C8' -0.1(4) . . . . ?
C5 C4 C3A C7A 0.7(4) . . . . ?
C5 C4 C3A C3 178.0(3) . . . . ?
N2 C3 C3A C4 -2.4(5) . . . . ?
C2 C3 C3A C4 -177.5(3) . . . . ?
N2 C3 C3A C7A 175.1(3) . . . . ?
C2 C3 C3A C7A 0.0(3) . . . . ?
C2 N1 C7A C7 178.3(3) . . . . ?
C2 N1 C7A C3A 0.3(3) . . . . ?
C6 C7 C7A N1 -178.0(3) . . . . ?
C6 C7 C7A C3A -0.2(4) . . . . ?
C4 C3A C7A N1 177.9(2) . . . . ?
C3 C3A C7A N1 -0.2(3) . . . . ?
C4 C3A C7A C7 -0.3(4) . . . . ?
C3 C3A C7A C7 -178.3(2) . . . . ?
C5' C4' C3A' C7A' 2.2(4) . . . . ?
C5' C4' C3A' C3' -179.6(3) . . . . ?
N2' C3' C3A' C4' 0.0(5) . . . . ?
C2' C3' C3A' C4' -178.8(3) . . . . ?
N2' C3' C3A' C7A' 178.5(3) . . . . ?
C2' C3' C3A' C7A' -0.4(3) . . . . ?
C6' C7' C7A' C3A' 1.0(4) . . . . ?
C6' C7' C7A' N1' 179.9(2) . . . . ?
C4' C3A' C7A' C7' -2.1(4) . . . . ?
C3' C3A' C7A' C7' 179.2(2) . . . . ?
C4' C3A' C7A' N1' 178.9(2) . . . . ?
C3' C3A' C7A' N1' 0.2(3) . . . . ?
C2' N1' C7A' C7' -178.8(3) . . . . ?
C2' N1' C7A' C3A' 0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.046

#===END

######################## NEXT STRUCTURE #####################################

data_2mrd4_s
_database_code_CSD               205333

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
? 
;
_chemical_name_common            
;
7,14-di-(4-fluorophenylamino)-6,13-di-(4-fluorophenylimino)pyrazino
[1,2-a:4,5-a']diindole 
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H24 F6 N6, 2(C3 H7 N O)'
_chemical_formula_sum            'C48 H38 F6 N8 O2'
_chemical_formula_weight         872.86

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'
F F 0.0171 0.0103 '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
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9770(11)
_cell_length_b                   10.8182(15)
_cell_length_c                   13.3466(19)
_cell_angle_alpha                109.812(2)
_cell_angle_beta                 93.863(2)
_cell_angle_gamma                95.079(3)
_cell_volume                     1073.5(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plates
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9668
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_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  '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            7601
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         28.31
_reflns_number_total             5195
_reflns_number_gt                2792
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 F^2^ against ALL reflections.  The weighted R-factor wR and 
goodness of fit S are based on F^2^, conventional R-factors R are based 
on F, with F set to zero for negative F^2^. The threshold expression of 
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
not relevant to the choice of reflections for refinement.  R-factors based 
on F^2^ 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/[\s^2^(Fo^2^)+(0.0720P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         5195
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1478
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_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
C2 C 0.5890(2) 0.94551(16) 0.41209(14) 0.0329(4) Uani 1 1 d . . .
C3 C 0.7188(2) 0.91337(16) 0.34848(14) 0.0326(4) Uani 1 1 d . . .
C4 C 0.9996(2) 0.81895(17) 0.37988(16) 0.0405(5) Uani 1 1 d . . .
H4 H 1.0419 0.8140 0.3155 0.049 Uiso 1 1 calc R . .
C5 C 1.0872(2) 0.78283(18) 0.45474(17) 0.0440(5) Uani 1 1 d . . .
C6 C 1.0318(2) 0.78950(18) 0.55199(16) 0.0446(5) Uani 1 1 d . . .
H6 H 1.0965 0.7619 0.5993 0.054 Uiso 1 1 calc R . .
C7 C 0.8803(2) 0.83715(17) 0.57866(15) 0.0410(5) Uani 1 1 d . . .
H7 H 0.8420 0.8444 0.6445 0.049 Uiso 1 1 calc R . .
C8 C 0.7948(2) 0.85918(18) 0.16224(15) 0.0386(4) Uani 1 1 d . . .
C9 C 0.8337(3) 0.9123(2) 0.08432(17) 0.0557(6) Uani 1 1 d . . .
H9 H 0.8235 1.0009 0.0960 0.067 Uiso 1 1 calc R . .
C10 C 0.8874(3) 0.8347(3) -0.01030(19) 0.0725(7) Uani 1 1 d . . .
H10 H 0.9109 0.8699 -0.0631 0.087 Uiso 1 1 calc R . .
C11 C 0.9055(3) 0.7055(3) -0.0253(2) 0.0694(7) Uani 1 1 d . . .
C12 C 0.8674(3) 0.6500(2) 0.04959(18) 0.0586(6) Uani 1 1 d . . .
H12 H 0.8799 0.5616 0.0375 0.070 Uiso 1 1 calc R . .
C13 C 0.8106(2) 0.72648(19) 0.14283(16) 0.0454(5) Uani 1 1 d . . .
H13 H 0.7823 0.6890 0.1936 0.055 Uiso 1 1 calc R . .
C14 C 0.5675(2) 1.00101(16) 0.60608(14) 0.0336(4) Uani 1 1 d . . .
C15 C 0.6309(2) 1.10945(18) 0.79349(14) 0.0384(4) Uani 1 1 d . . .
C16 C 0.6296(2) 1.24204(18) 0.80407(15) 0.0444(5) Uani 1 1 d . . .
H16 H 0.6356 1.2670 0.7441 0.053 Uiso 1 1 calc R . .
C17 C 0.6196(3) 1.3367(2) 0.90294(17) 0.0521(5) Uani 1 1 d . . .
H17 H 0.6180 1.4251 0.9100 0.063 Uiso 1 1 calc R . .
C18 C 0.6121(3) 1.2984(2) 0.98960(16) 0.0552(6) Uani 1 1 d . . .
C19 C 0.6192(3) 1.1701(2) 0.98357(17) 0.0568(6) Uani 1 1 d . . .
H19 H 0.6168 1.1470 1.0446 0.068 Uiso 1 1 calc R . .
C20 C 0.6301(3) 1.0761(2) 0.88485(16) 0.0488(5) Uani 1 1 d . . .
H20 H 0.6369 0.9888 0.8796 0.059 Uiso 1 1 calc R . .
C21 C 0.5603(4) 0.2855(3) 0.2900(2) 0.0879(9) Uani 1 1 d . . .
H21 H 0.4480 0.2490 0.2818 0.105 Uiso 1 1 calc R . .
C22 C 0.4634(9) 0.5004(5) 0.3486(4) 0.252(4) Uani 1 1 d . . .
H22A H 0.3533 0.4520 0.3223 0.378 Uiso 1 1 calc R . .
H22B H 0.4849 0.5635 0.3135 0.378 Uiso 1 1 calc R . .
H22C H 0.4681 0.5459 0.4244 0.378 Uiso 1 1 calc R . .
C23 C 0.7583(7) 0.4753(4) 0.3393(4) 0.181(2) Uani 1 1 d . . .
H23A H 0.8045 0.5028 0.4128 0.271 Uiso 1 1 calc R . .
H23B H 0.7590 0.5511 0.3172 0.271 Uiso 1 1 calc R . .
H23C H 0.8255 0.4132 0.2954 0.271 Uiso 1 1 calc R . .
C3A C 0.8425(2) 0.86403(16) 0.40456(14) 0.0335(4) Uani 1 1 d . . .
C7A C 0.7865(2) 0.87410(16) 0.50417(14) 0.0344(4) Uani 1 1 d . . .
F1 F 1.24123(14) 0.73904(12) 0.43384(10) 0.0651(4) Uani 1 1 d . . .
F2 F 0.9591(2) 0.62898(17) -0.11928(13) 0.1153(6) Uani 1 1 d . . .
F3 F 0.5998(2) 1.39184(13) 1.08701(10) 0.0844(5) Uani 1 1 d . . .
N1 N 0.63189(17) 0.92761(13) 0.51076(11) 0.0347(4) Uani 1 1 d . . .
N2 N 0.73505(19) 0.93997(14) 0.25538(12) 0.0383(4) Uani 1 1 d . . .
H2 H 0.7053 1.0141 0.2545 0.046 Uiso 1 1 calc R . .
N3 N 0.65149(19) 1.01211(15) 0.69454(12) 0.0400(4) Uani 1 1 d . . .
N4 N 0.5851(4) 0.4131(2) 0.32783(18) 0.0912(8) Uani 1 1 d . . .
O1 O 0.6602(2) 0.20715(15) 0.26391(14) 0.0746(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
C2 0.0333(10) 0.0315(9) 0.0329(10) 0.0100(7) 0.0006(8) 0.0063(8)
C3 0.0304(9) 0.0274(9) 0.0370(10) 0.0076(8) 0.0012(8) 0.0033(7)
C4 0.0342(10) 0.0378(10) 0.0473(12) 0.0105(9) 0.0074(8) 0.0081(8)
C5 0.0305(10) 0.0426(11) 0.0574(13) 0.0131(10) 0.0043(9) 0.0148(9)
C6 0.0418(11) 0.0412(11) 0.0511(13) 0.0157(9) -0.0039(9) 0.0148(9)
C7 0.0408(11) 0.0410(11) 0.0412(11) 0.0130(9) 0.0016(8) 0.0127(9)
C8 0.0304(10) 0.0433(11) 0.0414(11) 0.0124(9) 0.0067(8) 0.0072(8)
C9 0.0604(14) 0.0578(14) 0.0559(14) 0.0255(11) 0.0187(11) 0.0107(11)
C10 0.0779(18) 0.092(2) 0.0559(16) 0.0309(14) 0.0289(13) 0.0143(15)
C11 0.0658(16) 0.0776(18) 0.0516(15) -0.0002(13) 0.0253(12) 0.0168(14)
C12 0.0539(14) 0.0498(13) 0.0612(15) 0.0027(11) 0.0090(11) 0.0147(11)
C13 0.0424(12) 0.0427(12) 0.0473(12) 0.0099(9) 0.0055(9) 0.0070(9)
C14 0.0345(10) 0.0322(10) 0.0336(10) 0.0100(8) 0.0034(8) 0.0072(8)
C15 0.0336(10) 0.0414(11) 0.0379(11) 0.0109(9) -0.0007(8) 0.0076(8)
C16 0.0448(12) 0.0472(12) 0.0402(11) 0.0146(9) 0.0006(9) 0.0054(9)
C17 0.0572(14) 0.0415(12) 0.0513(14) 0.0095(10) -0.0029(10) 0.0056(10)
C18 0.0602(14) 0.0573(14) 0.0353(12) -0.0005(10) 0.0003(10) 0.0111(11)
C19 0.0689(15) 0.0670(15) 0.0365(12) 0.0190(11) 0.0044(10) 0.0152(12)
C20 0.0592(13) 0.0483(12) 0.0412(12) 0.0173(10) 0.0008(10) 0.0142(10)
C21 0.111(2) 0.077(2) 0.080(2) 0.0304(16) 0.0052(17) 0.0275(18)
C22 0.421(10) 0.220(5) 0.174(5) 0.077(4) 0.100(6) 0.261(6)
C23 0.266(7) 0.085(3) 0.167(4) 0.044(3) -0.043(4) -0.054(3)
C3A 0.0321(10) 0.0264(9) 0.0388(10) 0.0070(8) 0.0012(8) 0.0050(7)
C7A 0.0316(10) 0.0298(9) 0.0394(11) 0.0083(8) 0.0013(8) 0.0074(7)
F1 0.0420(7) 0.0827(9) 0.0785(9) 0.0305(7) 0.0123(6) 0.0334(6)
F2 0.1350(15) 0.1237(14) 0.0708(11) -0.0003(9) 0.0538(11) 0.0351(11)
F3 0.1201(13) 0.0744(9) 0.0437(8) -0.0024(7) 0.0078(8) 0.0262(8)
N1 0.0325(8) 0.0377(9) 0.0331(8) 0.0093(7) 0.0033(6) 0.0122(7)
N2 0.0430(9) 0.0338(8) 0.0411(9) 0.0145(7) 0.0084(7) 0.0103(7)
N3 0.0415(9) 0.0441(9) 0.0343(9) 0.0118(7) 0.0023(7) 0.0137(7)
N4 0.164(3) 0.0463(13) 0.0680(15) 0.0205(11) 0.0131(15) 0.0330(15)
O1 0.0909(13) 0.0483(10) 0.0841(12) 0.0217(9) -0.0024(10) 0.0197(9)

_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
C2 C3 1.376(2) . ?
C2 N1 1.419(2) . ?
C2 C14 1.462(2) 2_676 ?
C3 N2 1.379(2) . ?
C3 C3A 1.443(2) . ?
C4 C5 1.363(3) . ?
C4 C3A 1.405(2) . ?
C4 H4 0.9300 . ?
C5 F1 1.368(2) . ?
C5 C6 1.380(3) . ?
C6 C7 1.377(2) . ?
C6 H6 0.9300 . ?
C7 C7A 1.389(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(3) . ?
C8 C13 1.389(2) . ?
C8 N2 1.398(2) . ?
C9 C10 1.378(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.365(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(3) . ?
C11 F2 1.368(2) . ?
C12 C13 1.372(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 N3 1.281(2) . ?
C14 N1 1.410(2) . ?
C14 C2 1.462(2) 2_676 ?
C15 C20 1.384(3) . ?
C15 C16 1.394(2) . ?
C15 N3 1.413(2) . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.358(3) . ?
C17 H17 0.9300 . ?
C18 F3 1.366(2) . ?
C18 C19 1.369(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O1 1.197(3) . ?
C21 N4 1.290(3) . ?
C21 H21 0.9300 . ?
C22 N4 1.390(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 N4 1.457(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C3A C7A 1.403(2) . ?
C7A N1 1.403(2) . ?
N2 H2 0.8600 . ?

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
C3 C2 N1 109.18(14) . . ?
C3 C2 C14 130.10(16) . 2_676 ?
N1 C2 C14 120.59(14) . 2_676 ?
C2 C3 N2 125.33(15) . . ?
C2 C3 C3A 107.26(15) . . ?
N2 C3 C3A 126.94(15) . . ?
C5 C4 C3A 116.81(18) . . ?
C5 C4 H4 121.6 . . ?
C3A C4 H4 121.6 . . ?
C4 C5 F1 118.53(18) . . ?
C4 C5 C6 124.15(17) . . ?
F1 C5 C6 117.31(17) . . ?
C7 C6 C5 119.71(18) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C7A 117.93(18) . . ?
C6 C7 H7 121.0 . . ?
C7A C7 H7 121.0 . . ?
C9 C8 C13 118.66(18) . . ?
C9 C8 N2 118.73(17) . . ?
C13 C8 N2 122.56(17) . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 119.0(2) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 121.8(2) . . ?
C10 C11 F2 118.9(2) . . ?
C12 C11 F2 119.3(2) . . ?
C11 C12 C13 119.1(2) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C12 C13 C8 120.8(2) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
N3 C14 N1 117.23(15) . . ?
N3 C14 C2 129.31(16) . 2_676 ?
N1 C14 C2 113.46(15) . 2_676 ?
C20 C15 C16 118.45(17) . . ?
C20 C15 N3 119.64(16) . . ?
C16 C15 N3 121.54(17) . . ?
C17 C16 C15 120.53(18) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 118.83(19) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C17 C18 F3 118.7(2) . . ?
C17 C18 C19 122.60(19) . . ?
F3 C18 C19 118.6(2) . . ?
C18 C19 C20 118.35(19) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C19 C20 C15 121.13(19) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
O1 C21 N4 129.6(3) . . ?
O1 C21 H21 115.2 . . ?
N4 C21 H21 115.2 . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N4 C23 H23A 109.5 . . ?
N4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C7A C3A C4 119.56(16) . . ?
C7A C3A C3 107.60(14) . . ?
C4 C3A C3 132.73(17) . . ?
C7 C7A C3A 121.79(16) . . ?
C7 C7A N1 130.02(16) . . ?
C3A C7A N1 108.18(15) . . ?
C7A N1 C14 125.63(15) . . ?
C7A N1 C2 107.59(13) . . ?
C14 N1 C2 121.96(14) . . ?
C3 N2 C8 126.90(15) . . ?
C3 N2 H2 116.6 . . ?
C8 N2 H2 116.6 . . ?
C14 N3 C15 123.30(15) . . ?
C21 N4 C22 127.5(4) . . ?
C21 N4 C23 117.4(3) . . ?
C22 N4 C23 114.8(4) . . ?

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
N1 C2 C3 N2 -168.20(15) . . . . ?
C14 C2 C3 N2 7.7(3) 2_676 . . . ?
N1 C2 C3 C3A 4.35(19) . . . . ?
C14 C2 C3 C3A -179.77(16) 2_676 . . . ?
C3A C4 C5 F1 -179.66(15) . . . . ?
C3A C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C7 -1.1(3) . . . . ?
F1 C5 C6 C7 177.80(16) . . . . ?
C5 C6 C7 C7A 1.5(3) . . . . ?
C13 C8 C9 C10 -0.2(3) . . . . ?
N2 C8 C9 C10 -177.8(2) . . . . ?
C8 C9 C10 C11 -1.5(4) . . . . ?
C9 C10 C11 C12 1.8(4) . . . . ?
C9 C10 C11 F2 -179.9(2) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
F2 C11 C12 C13 -178.7(2) . . . . ?
C11 C12 C13 C8 -1.2(3) . . . . ?
C9 C8 C13 C12 1.5(3) . . . . ?
N2 C8 C13 C12 179.04(18) . . . . ?
C20 C15 C16 C17 -3.0(3) . . . . ?
N3 C15 C16 C17 -176.08(17) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 F3 -179.09(19) . . . . ?
C16 C17 C18 C19 2.0(3) . . . . ?
C17 C18 C19 C20 -1.7(4) . . . . ?
F3 C18 C19 C20 179.40(19) . . . . ?
C18 C19 C20 C15 -1.1(3) . . . . ?
C16 C15 C20 C19 3.4(3) . . . . ?
N3 C15 C20 C19 176.54(19) . . . . ?
C5 C4 C3A C7A 2.2(3) . . . . ?
C5 C4 C3A C3 177.88(17) . . . . ?
C2 C3 C3A C7A -2.84(19) . . . . ?
N2 C3 C3A C7A 169.55(16) . . . . ?
C2 C3 C3A C4 -178.93(18) . . . . ?
N2 C3 C3A C4 -6.5(3) . . . . ?
C6 C7 C7A C3A -0.1(3) . . . . ?
C6 C7 C7A N1 -178.50(17) . . . . ?
C4 C3A C7A C7 -1.8(3) . . . . ?
C3 C3A C7A C7 -178.50(16) . . . . ?
C4 C3A C7A N1 176.93(15) . . . . ?
C3 C3A C7A N1 0.23(19) . . . . ?
C7 C7A N1 C14 25.4(3) . . . . ?
C3A C7A N1 C14 -153.17(16) . . . . ?
C7 C7A N1 C2 -179.02(17) . . . . ?
C3A C7A N1 C2 2.40(18) . . . . ?
N3 C14 N1 C7A -5.1(3) . . . . ?
C2 C14 N1 C7A 174.69(15) 2_676 . . . ?
N3 C14 N1 C2 -157.44(16) . . . . ?
C2 C14 N1 C2 22.4(2) 2_676 . . . ?
C3 C2 N1 C7A -4.26(19) . . . . ?
C14 C2 N1 C7A 179.41(15) 2_676 . . . ?
C3 C2 N1 C14 152.40(16) . . . . ?
C14 C2 N1 C14 -23.9(3) 2_676 . . . ?
C2 C3 N2 C8 -142.45(18) . . . . ?
C3A C3 N2 C8 46.5(3) . . . . ?
C9 C8 N2 C3 -167.51(18) . . . . ?
C13 C8 N2 C3 15.0(3) . . . . ?
N1 C14 N3 C15 162.17(16) . . . . ?
C2 C14 N3 C15 -17.6(3) 2_676 . . . ?
C20 C15 N3 C14 139.0(2) . . . . ?
C16 C15 N3 C14 -48.0(3) . . . . ?
O1 C21 N4 C22 174.1(4) . . . . ?
O1 C21 N4 C23 1.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.040

#===END

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