##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N,N'-bis[(E)-quinoxalin-2-ylmethylidene]propane-1,3-diamine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H18 N6'
_chemical_formula_sum     'C21 H18 N6'
_chemical_formula_iupac     'C21 H18 N6'
_chemical_formula_weight     354.41
_chemical_melting_point     ?
_symmetry_cell_setting     ' monoclinic '
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
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     10.371(2)
_cell_length_b     9.180(2)
_cell_length_c     19.084(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.209(4)
_cell_angle_gamma     90.00
_cell_volume     1817.0(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1695
_cell_measurement_theta_min     2.60
_cell_measurement_theta_max     28.2
_cell_measurement_temperature     298(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.296
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     744
_exptl_absorpt_coefficient_mu     0.082
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2001)'
_exptl_absorpt_correction_T_min     0.9642
_exptl_absorpt_correction_T_max     0.9903
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5277
_diffrn_reflns_av_R_equivalents     0.0226
_diffrn_reflns_av_sigmaI/netI     0.0281
_diffrn_reflns_theta_min     2.13
_diffrn_reflns_theta_max     28.20
_diffrn_reflns_theta_full     28.20
_diffrn_measured_fraction_theta_max     0.930
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     25
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 >
σ(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.
;
_reflns_number_total     2086
_reflns_number_gt     1695
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0921
_refine_ls_R_factor_gt     0.0760
_refine_ls_wR_factor_gt     0.1610
_refine_ls_wR_factor_ref     0.1689
_refine_ls_goodness_of_fit_ref     1.184
_refine_ls_restrained_S_all     1.184
_refine_ls_number_reflns     2086
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0539P)²+1.6232P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.225
_refine_diff_density_min     -0.171
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT (Bruker, 2000)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                        'SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'publCIF (Westrip, 2009)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.41189(18) 0.8333(2) 0.45574(10) 0.0476(5) Uani d . 1 . .
    N N2 0.23634(17) 1.0385(2) 0.51175(9) 0.0449(5) Uani d . 1 . .
    N N3 0.18137(18) 1.1080(2) 0.33187(10) 0.0493(5) Uani d . 1 . .
    C C1 0.3408(2) 0.9176(3) 0.41655(12) 0.0459(6) Uani d . 1 . .
    C C2 0.3974(2) 0.8495(2) 0.52678(11) 0.0411(5) Uani d . 1 . .
    C C3 0.4716(2) 0.7635(3) 0.57323(13) 0.0515(6) Uani d . 1 . .
    C C4 0.4577(3) 0.7802(3) 0.64355(14) 0.0578(7) Uani d . 1 . .
    C C5 0.3708(3) 0.8820(3) 0.67140(13) 0.0564(7) Uani d . 1 . .
    C C6 0.2979(2) 0.9656(3) 0.62794(12) 0.0505(6) Uani d . 1 . .
    C C7 0.3095(2) 0.9523(2) 0.55458(11) 0.0408(5) Uani d . 1 . .
    C C8 0.2524(2) 1.0207(2) 0.44395(11) 0.0422(5) Uani d . 1 . .
    C C9 0.1731(2) 1.1136(3) 0.39743(12) 0.0478(6) Uani d . 1 . .
    C C10 0.0934(3) 1.2010(3) 0.29216(13) 0.0507(6) Uani d . 1 . .
    C C11 0.0000 1.1091(4) 0.2500 0.0509(8) Uani d S 1 . .
    H H1 0.347(2) 0.908(2) 0.3673(12) 0.042(6) Uiso d . 1 . .
    H H3 0.528(3) 0.693(3) 0.5536(14) 0.070(8) Uiso d . 1 . .
    H H4 0.506(2) 0.724(3) 0.6750(12) 0.049(6) Uiso d . 1 . .
    H H5 0.362(3) 0.890(3) 0.7196(14) 0.067(8) Uiso d . 1 . .
    H H6 0.237(2) 1.038(3) 0.6460(12) 0.052(7) Uiso d . 1 . .
    H H9 0.117(2) 1.176(3) 0.4201(13) 0.054(7) Uiso d . 1 . .
    H H10A 0.149(2) 1.260(3) 0.2574(13) 0.058(7) Uiso d . 1 . .
    H H10B 0.048(2) 1.269(3) 0.3223(13) 0.059(7) Uiso d . 1 . .
    H H11A -0.046(3) 1.044(3) 0.2810(13) 0.066(8) Uiso d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    N1 0.0452(11) 0.0499(11) 0.0478(11) 0.0071(9) 0.0016(8) -0.0062(9)
    N2 0.0433(10) 0.0472(11) 0.0442(10) 0.0045(8) -0.0001(8) -0.0039(8)
    N3 0.0484(11) 0.0549(12) 0.0446(11) 0.0055(9) -0.0058(8) -0.0033(9)
    C1 0.0444(12) 0.0531(13) 0.0402(12) 0.0029(11) 0.0007(9) -0.0071(10)
    C2 0.0362(11) 0.0389(11) 0.0483(12) -0.0040(9) -0.0018(9) -0.0018(9)
    C3 0.0488(14) 0.0469(13) 0.0589(15) 0.0046(11) -0.0043(11) 0.0016(11)
    C4 0.0642(17) 0.0538(15) 0.0553(16) 0.0009(13) -0.0125(12) 0.0126(12)
    C5 0.0658(17) 0.0622(16) 0.0412(13) -0.0040(13) -0.0023(11) 0.0017(12)
    C6 0.0529(14) 0.0541(14) 0.0445(13) 0.0002(12) 0.0038(10) -0.0031(11)
    C7 0.0373(11) 0.0412(11) 0.0440(12) -0.0028(9) -0.0006(9) -0.0016(9)
    C8 0.0387(11) 0.0439(12) 0.0440(12) 0.0005(9) -0.0009(9) -0.0045(9)
    C9 0.0462(13) 0.0499(13) 0.0473(13) 0.0086(11) -0.0015(10) -0.0065(11)
    C10 0.0554(15) 0.0503(14) 0.0463(13) 0.0064(12) -0.0089(11) -0.0022(11)
    C11 0.053(2) 0.0471(19) 0.053(2) 0.000 -0.0079(16) 0.000
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C1 . 1.303(3) n
    N1 C2 . 1.373(3) n
    N2 C8 . 1.315(3) n
    N2 C7 . 1.366(3) n
    N3 C9 . 1.256(3) n
    N3 C10 . 1.459(3) n
    C1 C8 . 1.419(3) no
    C1 H1 . 0.95(2) no
    C2 C3 . 1.413(3) no
    C2 C7 . 1.417(3) no
    C3 C4 . 1.359(4) no
    C3 H3 . 0.95(3) no
    C4 C5 . 1.404(4) no
    C4 H4 . 0.94(2) no
    C5 C6 . 1.358(3) no
    C5 H5 . 0.93(3) no
    C6 C7 . 1.411(3) no
    C6 H6 . 0.98(2) no
    C8 C9 . 1.478(3) no
    C9 H9 . 0.93(3) no
    C10 C11 . 1.514(3) n
    C10 H10A . 1.03(3) no
    C10 H10B . 0.98(3) no
    C11 C10 2 1.514(3) n
    C11 H11A . 0.97(2) no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 N1 C2 . . 116.03(19) n
    C8 N2 C7 . . 116.41(19) n
    C9 N3 C10 . . 116.7(2) n
    N1 C1 C8 . . 123.4(2) n
    N1 C1 H1 . . 118.7(14) no
    C8 C1 H1 . . 117.9(14) no
    N1 C2 C3 . . 119.9(2) n
    N1 C2 C7 . . 120.97(19) n
    C3 C2 C7 . . 119.2(2) no
    C4 C3 C2 . . 119.8(2) no
    C4 C3 H3 . . 122.3(16) no
    C2 C3 H3 . . 117.8(16) no
    C3 C4 C5 . . 121.3(2) no
    C3 C4 H4 . . 120.9(15) no
    C5 C4 H4 . . 117.9(15) no
    C6 C5 C4 . . 120.1(2) no
    C6 C5 H5 . . 120.3(17) no
    C4 C5 H5 . . 119.5(17) no
    C5 C6 C7 . . 120.5(2) no
    C5 C6 H6 . . 121.9(13) no
    C7 C6 H6 . . 117.6(13) no
    N2 C7 C6 . . 119.6(2) n
    N2 C7 C2 . . 121.25(19) n
    C6 C7 C2 . . 119.1(2) no
    N2 C8 C1 . . 122.0(2) n
    N2 C8 C9 . . 116.5(2) n
    C1 C8 C9 . . 121.5(2) no
    N3 C9 C8 . . 122.3(2) n
    N3 C9 H9 . . 122.5(15) no
    C8 C9 H9 . . 115.2(15) no
    N3 C10 C11 . . 110.3(2) n
    N3 C10 H10A . . 107.0(14) no
    C11 C10 H10A . . 107.9(14) no
    N3 C10 H10B . . 111.9(15) no
    C11 C10 H10B . . 111.0(15) no
    H10A C10 H10B . . 108(2) no
    C10 C11 C10 . 2 112.3(3) n
    C10 C11 H11A . . 109.4(15) no
    C10 C11 H11A 2 . 110.7(16) no
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C2 N1 C1 C8 . . . . -0.3(3) no
    C1 N1 C2 C3 . . . . -179.4(2) n
    C1 N1 C2 C7 . . . . 0.2(3) no
    N1 C2 C3 C4 . . . . 179.6(2) n
    C7 C2 C3 C4 . . . . 0.1(3) no
    C2 C3 C4 C5 . . . . -0.1(4) no
    C3 C4 C5 C6 . . . . 0.4(4) no
    C4 C5 C6 C7 . . . . -0.6(4) no
    C8 N2 C7 C6 . . . . 179.8(2) n
    C8 N2 C7 C2 . . . . -0.1(3) no
    C5 C6 C7 N2 . . . . -179.3(2) n
    C5 C6 C7 C2 . . . . 0.6(4) no
    N1 C2 C7 N2 . . . . 0.0(3) no
    C3 C2 C7 N2 . . . . 179.5(2) n
    N1 C2 C7 C6 . . . . -179.8(2) n
    C3 C2 C7 C6 . . . . -0.3(3) no
    C7 N2 C8 C1 . . . . 0.0(3) no
    C7 N2 C8 C9 . . . . 179.81(19) n
    N1 C1 C8 N2 . . . . 0.2(4) no
    N1 C1 C8 C9 . . . . -179.6(2) n
    C10 N3 C9 C8 . . . . 177.4(2) n
    N2 C8 C9 N3 . . . . 178.9(2) n
    C1 C8 C9 N3 . . . . -1.3(4) no
    C9 N3 C10 C11 . . . . -114.7(2) no
    N3 C10 C11 C10 . . . . 180.0(2) n
data_II
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N,N'-bis[(E)-quinoxalin-2-ylmethylidene]butane-1,4-diamine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H20 N6'
_chemical_formula_sum     'C22 H20 N6'
_chemical_formula_iupac     'C22 H20 N6'
_chemical_formula_weight     368.44
_chemical_melting_point     ?
_symmetry_cell_setting     'monoclinic'
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc '
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     4.4819(12)
_cell_length_b     5.3333(14)
_cell_length_c     39.456(10)
_cell_angle_alpha     90.00
_cell_angle_beta     92.266(4)
_cell_angle_gamma     90.00
_cell_volume     942.4(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1748
_cell_measurement_theta_min     2.66
_cell_measurement_theta_max     27.940
_cell_measurement_temperature     298(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.75
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.298
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     388
_exptl_absorpt_coefficient_mu     0.081
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2001)'
_exptl_absorpt_correction_T_min     0.9415
_exptl_absorpt_correction_T_max     0.9887
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5220
_diffrn_reflns_av_R_equivalents     0.0202
_diffrn_reflns_av_sigmaI/netI     0.0269
_diffrn_reflns_theta_min     2.07
_diffrn_reflns_theta_max     27.94
_diffrn_reflns_theta_full     27.94
_diffrn_measured_fraction_theta_max     0.951
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -3
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -51
_diffrn_reflns_limit_l_max     41
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 >
σ(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.
;
_reflns_number_total     2132
_reflns_number_gt     1748
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0839
_refine_ls_R_factor_gt     0.0712
_refine_ls_wR_factor_gt     0.1784
_refine_ls_wR_factor_ref     0.1862
_refine_ls_goodness_of_fit_ref     1.140
_refine_ls_restrained_S_all     1.140
_refine_ls_number_reflns     2132
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0658P)²+0.4677P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.209
_refine_diff_density_min     -0.169
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT (Bruker, 2000)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                        'SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'publCIF (Westrip, 2009)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 -0.1263(5) 0.3610(4) 0.11524(5) 0.0615(6) Uani d . 1 . .
    N N2 0.2097(4) -0.0513(4) 0.14068(5) 0.0546(5) Uani d . 1 . .
    N N3 0.3994(4) -0.0928(4) 0.05486(5) 0.0581(6) Uani d . 1 . .
    C C1 0.0387(5) 0.0910(4) 0.16130(5) 0.0497(5) Uani d . 1 . .
    C C2 0.0304(7) 0.0295(6) 0.19610(7) 0.0668(7) Uani d . 1 . .
    C C3 -0.1367(7) 0.1693(6) 0.21702(7) 0.0728(8) Uani d . 1 . .
    C C4 -0.2975(7) 0.3749(6) 0.20463(7) 0.0715(8) Uani d . 1 . .
    C C5 -0.2954(6) 0.4394(6) 0.17123(7) 0.0649(7) Uani d . 1 . .
    C C6 -0.1263(5) 0.2972(4) 0.14894(6) 0.0499(5) Uani d . 1 . .
    C C7 0.0368(6) 0.2207(5) 0.09630(6) 0.0577(6) Uani d . 1 . .
    C C8 0.2068(5) 0.0137(4) 0.10858(5) 0.0491(5) Uani d . 1 . .
    C C9 0.3930(5) -0.1356(5) 0.08610(6) 0.0554(6) Uani d . 1 . .
    C C10 0.5906(6) -0.2570(6) 0.03541(7) 0.0611(7) Uani d . 1 . .
    C C11 0.4061(6) -0.4173(5) 0.01103(6) 0.0557(6) Uani d . 1 . .
    H H2 0.144(6) -0.111(6) 0.2039(7) 0.076(9) Uiso d . 1 . .
    H H3 -0.148(6) 0.127(6) 0.2400(8) 0.077(8) Uiso d . 1 . .
    H H4 -0.419(7) 0.470(6) 0.2196(7) 0.086(9) Uiso d . 1 . .
    H H5 -0.412(6) 0.574(6) 0.1629(7) 0.069(8) Uiso d . 1 . .
    H H8 0.037(6) 0.260(5) 0.0724(7) 0.067(7) Uiso d . 1 . .
    H H9 0.505(5) -0.266(5) 0.0969(6) 0.056(7) Uiso d . 1 . .
    H H10A 0.718(6) -0.365(6) 0.0506(7) 0.075(8) Uiso d . 1 . .
    H H10B 0.721(6) -0.143(6) 0.0216(7) 0.071(8) Uiso d . 1 . .
    H H11A 0.274(6) -0.522(6) 0.0237(7) 0.076(8) Uiso d . 1 . .
    H H11B 0.287(6) -0.306(6) -0.0034(7) 0.080(9) Uiso d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    N1 0.0702(13) 0.0580(12) 0.0568(12) 0.0166(10) 0.0079(9) -0.0006(10)
    N2 0.0576(11) 0.0531(11) 0.0534(11) 0.0065(9) 0.0039(9) -0.0025(9)
    N3 0.0607(12) 0.0601(13) 0.0540(12) 0.0130(10) 0.0073(9) -0.0081(9)
    C1 0.0527(12) 0.0499(13) 0.0467(12) -0.0054(10) 0.0051(9) -0.0061(9)
    C2 0.0803(18) 0.0638(17) 0.0567(14) 0.0041(15) 0.0085(13) 0.0037(13)
    C3 0.090(2) 0.080(2) 0.0495(14) -0.0069(17) 0.0173(13) -0.0035(13)
    C4 0.0740(17) 0.0775(19) 0.0645(16) -0.0013(15) 0.0237(13) -0.0189(15)
    C5 0.0643(16) 0.0621(16) 0.0689(16) 0.0071(13) 0.0119(13) -0.0127(13)
    C6 0.0500(12) 0.0464(12) 0.0538(12) -0.0034(10) 0.0068(9) -0.0062(10)
    C7 0.0683(15) 0.0571(14) 0.0482(13) 0.0127(12) 0.0075(11) -0.0004(11)
    C8 0.0483(11) 0.0496(13) 0.0495(12) 0.0013(10) 0.0034(9) -0.0057(10)
    C9 0.0552(13) 0.0537(14) 0.0571(14) 0.0104(11) 0.0009(10) -0.0029(11)
    C10 0.0604(15) 0.0656(16) 0.0578(14) 0.0138(13) 0.0104(12) -0.0088(12)
    C11 0.0570(14) 0.0578(15) 0.0533(13) 0.0107(12) 0.0162(11) -0.0024(11)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C7 . 1.302(3) n
    N1 C6 . 1.373(3) n
    N2 C8 . 1.313(3) n
    N2 C1 . 1.369(3) n
    N3 C9 . 1.255(3) n
    N3 C10 . 1.463(3) n
    C1 C6 . 1.402(3) ?
    C1 C2 . 1.414(3) ?
    C2 C3 . 1.359(4) ?
    C2 H2 . 0.95(3) ?
    C3 C4 . 1.390(4) ?
    C3 H3 . 0.94(3) ?
    C4 C5 . 1.363(4) ?
    C4 H4 . 0.96(3) ?
    C5 C6 . 1.405(3) ?
    C5 H5 . 0.94(3) ?
    C7 C8 . 1.416(3) ?
    C7 H8 . 0.96(3) ?
    C8 C9 . 1.476(3) ?
    C9 H9 . 0.95(3) ?
    C10 C11 . 1.509(4) n
    C10 H10A . 0.99(3) ?
    C10 H10B . 1.02(3) ?
    C11 C11 3_645 1.517(4) n
    C11 H11A . 0.97(3) ?
    C11 H11B . 0.97(3) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C7 N1 C6 . . 115.8(2) n
    C8 N2 C1 . . 116.2(2) n
    C9 N3 C10 . . 116.3(2) n
    N2 C1 C6 . . 121.9(2) n
    N2 C1 C2 . . 119.0(2) n
    C6 C1 C2 . . 119.1(2) ?
    C3 C2 C1 . . 119.9(3) ?
    C3 C2 H2 . . 122.5(17) ?
    C1 C2 H2 . . 117.6(17) ?
    C2 C3 C4 . . 120.6(3) ?
    C2 C3 H3 . . 120.6(18) ?
    C4 C3 H3 . . 118.8(18) ?
    C5 C4 C3 . . 121.0(3) ?
    C5 C4 H4 . . 119.2(19) ?
    C3 C4 H4 . . 119.8(19) ?
    C4 C5 C6 . . 119.6(3) ?
    C4 C5 H5 . . 120.4(17) ?
    C6 C5 H5 . . 119.9(17) ?
    N1 C6 C1 . . 120.7(2) n
    N1 C6 C5 . . 119.5(2) n
    C1 C6 C5 . . 119.7(2) ?
    N1 C7 C8 . . 123.9(2) n
    N1 C7 H8 . . 117.2(16) ?
    C8 C7 H8 . . 118.9(16) ?
    N2 C8 C7 . . 121.4(2) n
    N2 C8 C9 . . 116.9(2) n
    C7 C8 C9 . . 121.6(2) ?
    N3 C9 C8 . . 121.8(2) n
    N3 C9 H9 . . 122.8(14) ?
    C8 C9 H9 . . 115.3(14) ?
    N3 C10 C11 . . 110.8(2) n
    N3 C10 H10A . . 111.4(15) ?
    C11 C10 H10A . . 110.1(17) ?
    N3 C10 H10B . . 106.7(16) ?
    C11 C10 H10B . . 107.9(15) ?
    H10A C10 H10B . . 110(2) ?
    C10 C11 C11 . 3_645 113.1(3) n
    C10 C11 H11A . . 109.2(17) ?
    C11 C11 H11A 3_645 . 108.9(17) ?
    C10 C11 H11B . . 107.6(18) ?
    C11 C11 H11B 3_645 . 108.8(17) ?
    H11A C11 H11B . . 109(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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C8 N2 C1 C6 . . . . -1.0(3) ?
    C8 N2 C1 C2 . . . . 179.5(2) n
    N2 C1 C2 C3 . . . . 179.7(2) n
    C6 C1 C2 C3 . . . . 0.2(4) ?
    C1 C2 C3 C4 . . . . -0.8(5) ?
    C2 C3 C4 C5 . . . . 0.9(5) ?
    C3 C4 C5 C6 . . . . -0.5(4) ?
    C7 N1 C6 C1 . . . . -0.7(3) ?
    C7 N1 C6 C5 . . . . 179.7(2) n
    N2 C1 C6 N1 . . . . 1.2(3) ?
    C2 C1 C6 N1 . . . . -179.3(2) n
    N2 C1 C6 C5 . . . . -179.2(2) n
    C2 C1 C6 C5 . . . . 0.3(3) ?
    C4 C5 C6 N1 . . . . 179.5(2) n
    C4 C5 C6 C1 . . . . -0.1(4) ?
    C6 N1 C7 C8 . . . . 0.0(4) ?
    C1 N2 C8 C7 . . . . 0.3(3) ?
    C1 N2 C8 C9 . . . . 179.20(19) n
    N1 C7 C8 N2 . . . . 0.2(4) ?
    N1 C7 C8 C9 . . . . -178.6(2) n
    C10 N3 C9 C8 . . . . -179.2(2) n
    N2 C8 C9 N3 . . . . 178.1(2) n
    C7 C8 C9 N3 . . . . -3.1(4) ?
    C9 N3 C10 C11 . . . . 113.4(3) ?
    N3 C10 C11 C11 . . . 3_645 177.3(3) n
data_global
_journal_date_recd_electronic     2009-09-23
_journal_date_accepted     2009-10-28
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2009
_journal_volume     65
_journal_issue     12
_journal_page_first     o612
_journal_page_last     o614
_journal_paper_category     FO
_journal_coeditor_code     SK3348
_publ_contact_author_name     'Yusuff, K. K. M.'
_publ_contact_author_address
;
Department of Applied Chemistry
Cochin University of Science and Technology
Cochin-682 022, Kerala, India.
;
_publ_contact_author_email     'yusuff@cusat.ac.in.  '
_publ_contact_author_fax     +91-484-2577595
_publ_contact_author_phone     '+91-484-2575804 '
_publ_section_title
;
Two novel bis-azomethines derived from quinoxaline-2-carbaldehyde
;
loop_
    _publ_author_name
    _publ_author_address
    'Varghese, Digna'
;
Department of Applied Chemistry
Cochin University of Science and Technology
Cochin 682 022
Kerala
India
;
    'V. Arun'
;
Department of Applied Chemistry
Cochin University of Science and Technology
Cochin 682 022
Kerala
India
;
    'P. P. Robinson'
;
Department of Applied Chemistry
Cochin University of Science and Technology
Cochin 682 022
Kerala
India
;
    'Sebastian, Manju'
;
Department of Applied Chemistry
Cochin University of Science and Technology
Cochin 682 022
Kerala
India
;
    'P. Leeju'
;
Department of Applied Chemistry
Cochin University of Science and Technology
Cochin 682 022
Kerala
India
;
    'G. Varsha'
;
Department of Applied Chemistry
Cochin University of Science and Technology
Cochin 682 022
Kerala
India
;
    'Yusuff, K. K. M.'
;
Department of Applied Chemistry
Cochin University of Science and Technology
Cochin 682 022
Kerala
India
;
