##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# 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
;
1,1,2,2-Tetrakis(1,3-benzoxazol-2-yl)ethene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C30 H16 N4 O4'
_chemical_formula_sum     'C30 H16 N4 O4'
_chemical_formula_iupac     'C30 H16 N4 O4'
_chemical_formula_weight     496.47
_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     9.2697(9)
_cell_length_b     16.1943(16)
_cell_length_c     8.0332(8)
_cell_angle_alpha     90.00
_cell_angle_beta     104.395(2)
_cell_angle_gamma     90.00
_cell_volume     1168.1(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3523
_cell_measurement_theta_min     2.516
_cell_measurement_theta_max     28.271
_cell_measurement_temperature     273(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.412
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     512
_exptl_absorpt_coefficient_mu     0.096
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1997)'
_exptl_absorpt_correction_T_min     0.9716
_exptl_absorpt_correction_T_max     0.9857
_exptl_special_details
;
;
_diffrn_ambient_temperature     273(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 APEX CCD area-detector'
_diffrn_measurement_method     '\w'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6999
_diffrn_reflns_av_R_equivalents     0.0213
_diffrn_reflns_av_sigmaI/netI     0.0248
_diffrn_reflns_theta_min     2.27
_diffrn_reflns_theta_max     28.27
_diffrn_reflns_theta_full     26.50
_diffrn_measured_fraction_theta_max     0.936
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     7
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     2717
_reflns_number_gt     2458
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0534
_refine_ls_R_factor_gt     0.0485
_refine_ls_wR_factor_gt     0.1171
_refine_ls_wR_factor_ref     0.1208
_refine_ls_goodness_of_fit_ref     1.064
_refine_ls_restrained_S_all     1.064
_refine_ls_number_reflns     2717
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+0.8168P] where P=(Fo^2^+2Fc^2^)/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     0.368
_refine_diff_density_min     -0.300
_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'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2002)'
_computing_data_reduction     'SAINT (Bruker, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Mercury (Macrae <i>et al.</i>, 2008)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.02783(16) 0.46822(9) 0.55330(19) 0.0186(3) Uani d . 1 1 . .
    C C2 -0.02821(16) 0.44239(9) 0.69934(19) 0.0199(3) Uani d . 1 1 . .
    N N3 0.01487(14) 0.37588(8) 0.78861(16) 0.0197(3) Uani d . 1 1 . .
    C C4 -0.06473(16) 0.37680(9) 0.91493(19) 0.0196(3) Uani d . 1 1 . .
    C C5 -0.06558(18) 0.32189(10) 1.0482(2) 0.0240(3) Uani d . 1 1 . .
    H H5 -0.0059 0.2749 1.0664 0.029 Uiso calc R 1 1 . .
    C C6 -0.15995(18) 0.34088(10) 1.1524(2) 0.0258(3) Uani d . 1 1 . .
    H H6 -0.1640 0.3055 1.2423 0.031 Uiso calc R 1 1 . .
    C C7 -0.24923(18) 0.41171(10) 1.1263(2) 0.0262(4) Uani d . 1 1 . .
    H H7 -0.3114 0.4218 1.1988 0.031 Uiso calc R 1 1 . .
    C C8 -0.24768(18) 0.46738(10) 0.9955(2) 0.0246(3) Uani d . 1 1 . .
    H H8 -0.3060 0.5148 0.9782 0.029 Uiso calc R 1 1 . .
    C C9 -0.15338(16) 0.44734(9) 0.89261(19) 0.0199(3) Uani d . 1 1 . .
    O O10 -0.12962(12) 0.48989(7) 0.75253(14) 0.0217(3) Uani d . 1 1 . .
    C C11 0.15956(17) 0.42084(10) 0.53413(19) 0.0217(3) Uani d . 1 1 . .
    N N12 0.29464(13) 0.44984(7) 0.58136(16) 0.0179(3) Uani d . 1 1 . .
    C C13 0.38086(17) 0.38841(9) 0.53122(19) 0.0194(3) Uani d . 1 1 . .
    C C14 0.53275(17) 0.38556(10) 0.5437(2) 0.0251(3) Uani d . 1 1 . .
    H H14 0.5959 0.4286 0.5920 0.030 Uiso calc R 1 1 . .
    C C15 0.58507(18) 0.31551(11) 0.4807(2) 0.0284(4) Uani d . 1 1 . .
    H H15 0.6863 0.3111 0.4872 0.034 Uiso calc R 1 1 . .
    C C16 0.4904(2) 0.25091(11) 0.4074(2) 0.0309(4) Uani d . 1 1 . .
    H H16 0.5307 0.2048 0.3666 0.037 Uiso calc R 1 1 . .
    C C17 0.33806(19) 0.25342(10) 0.3935(2) 0.0284(4) Uani d . 1 1 . .
    H H17 0.2746 0.2106 0.3450 0.034 Uiso calc R 1 1 . .
    C C18 0.28725(16) 0.32445(9) 0.45730(19) 0.0205(3) Uani d . 1 1 . .
    O O19 0.14322(12) 0.34621(7) 0.46062(15) 0.0258(3) Uani d . 1 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
    C1 0.0167(7) 0.0186(7) 0.0206(7) -0.0016(5) 0.0050(5) -0.0009(5)
    C2 0.0164(7) 0.0216(7) 0.0211(7) -0.0023(5) 0.0037(6) -0.0013(6)
    N3 0.0192(6) 0.0191(6) 0.0211(6) -0.0002(5) 0.0057(5) 0.0020(5)
    C4 0.0190(7) 0.0195(7) 0.0197(7) -0.0035(5) 0.0037(6) -0.0023(5)
    C5 0.0274(8) 0.0202(7) 0.0233(8) -0.0018(6) 0.0044(6) 0.0016(6)
    C6 0.0314(8) 0.0260(8) 0.0199(7) -0.0096(6) 0.0062(6) -0.0002(6)
    C7 0.0272(8) 0.0306(8) 0.0236(8) -0.0072(6) 0.0114(6) -0.0070(6)
    C8 0.0236(8) 0.0249(8) 0.0266(8) -0.0004(6) 0.0088(6) -0.0039(6)
    C9 0.0202(7) 0.0197(7) 0.0189(7) -0.0033(5) 0.0035(5) -0.0007(6)
    O10 0.0217(5) 0.0216(5) 0.0234(5) 0.0014(4) 0.0084(4) 0.0019(4)
    C11 0.0239(8) 0.0227(7) 0.0197(7) 0.0061(6) 0.0080(6) 0.0067(6)
    N12 0.0155(6) 0.0149(6) 0.0246(6) 0.0013(4) 0.0075(5) 0.0011(5)
    C13 0.0210(7) 0.0180(7) 0.0202(7) 0.0026(5) 0.0069(6) 0.0017(5)
    C14 0.0202(7) 0.0283(8) 0.0270(8) -0.0029(6) 0.0062(6) 0.0031(6)
    C15 0.0203(8) 0.0376(9) 0.0291(8) 0.0079(7) 0.0097(6) 0.0068(7)
    C16 0.0343(9) 0.0297(9) 0.0308(9) 0.0113(7) 0.0123(7) -0.0028(7)
    C17 0.0311(9) 0.0246(8) 0.0291(8) -0.0005(6) 0.0068(7) -0.0056(6)
    C18 0.0192(7) 0.0223(7) 0.0200(7) 0.0019(6) 0.0047(6) 0.0012(6)
    O19 0.0220(6) 0.0265(6) 0.0283(6) 0.0015(4) 0.0051(5) -0.0013(5)
_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
    C1 C1 3_566 1.356(3) ?
    C1 C2 . 1.458(2) ?
    C1 C11 . 1.482(2) ?
    C2 N3 . 1.3006(19) ?
    C2 O10 . 1.3628(18) ?
    N3 C4 . 1.3952(19) ?
    C4 C9 . 1.393(2) ?
    C4 C5 . 1.394(2) ?
    C5 C6 . 1.387(2) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.399(2) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.387(2) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.382(2) ?
    C8 H8 . 0.9300 ?
    C9 O10 . 1.3830(18) ?
    C11 N12 . 1.302(2) ?
    C11 O19 . 1.3370(19) ?
    N12 C13 . 1.3966(18) ?
    C13 C18 . 1.386(2) ?
    C13 C14 . 1.387(2) ?
    C14 C15 . 1.379(2) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.398(3) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.389(2) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.388(2) ?
    C17 H17 . 0.9300 ?
    C18 O19 . 1.3874(18) ?
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 C1 C2 3_566 . 124.77(17) ?
    C1 C1 C11 3_566 . 121.42(17) ?
    C2 C1 C11 . . 113.75(12) ?
    N3 C2 O10 . . 115.83(13) ?
    N3 C2 C1 . . 124.01(14) ?
    O10 C2 C1 . . 120.14(13) ?
    C2 N3 C4 . . 104.29(12) ?
    C9 C4 C5 . . 120.43(14) ?
    C9 C4 N3 . . 108.48(13) ?
    C5 C4 N3 . . 131.09(14) ?
    C6 C5 C4 . . 116.56(15) ?
    C6 C5 H5 . . 121.7 ?
    C4 C5 H5 . . 121.7 ?
    C5 C6 C7 . . 121.96(15) ?
    C5 C6 H6 . . 119.0 ?
    C7 C6 H6 . . 119.0 ?
    C8 C7 C6 . . 121.95(15) ?
    C8 C7 H7 . . 119.0 ?
    C6 C7 H7 . . 119.0 ?
    C9 C8 C7 . . 115.30(15) ?
    C9 C8 H8 . . 122.4 ?
    C7 C8 H8 . . 122.4 ?
    C8 C9 O10 . . 128.44(14) ?
    C8 C9 C4 . . 123.79(14) ?
    O10 C9 C4 . . 107.77(13) ?
    C2 O10 C9 . . 103.63(11) ?
    N12 C11 O19 . . 116.73(13) ?
    N12 C11 C1 . . 122.70(14) ?
    O19 C11 C1 . . 120.53(13) ?
    C11 N12 C13 . . 103.70(12) ?
    C18 C13 C14 . . 121.47(14) ?
    C18 C13 N12 . . 108.27(13) ?
    C14 C13 N12 . . 130.25(14) ?
    C15 C14 C13 . . 116.37(15) ?
    C15 C14 H14 . . 121.8 ?
    C13 C14 H14 . . 121.8 ?
    C14 C15 C16 . . 121.96(15) ?
    C14 C15 H15 . . 119.0 ?
    C16 C15 H15 . . 119.0 ?
    C17 C16 C15 . . 122.06(15) ?
    C17 C16 H16 . . 119.0 ?
    C15 C16 H16 . . 119.0 ?
    C18 C17 C16 . . 115.22(15) ?
    C18 C17 H17 . . 122.4 ?
    C16 C17 H17 . . 122.4 ?
    C13 C18 O19 . . 107.75(13) ?
    C13 C18 C17 . . 122.92(14) ?
    O19 C18 C17 . . 129.34(14) ?
    C11 O19 C18 . . 103.54(12) ?
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
    C1 C1 C2 N3 3_566 . . . 171.93(18) ?
    C11 C1 C2 N3 . . . . -11.0(2) ?
    C1 C1 C2 O10 3_566 . . . -9.6(3) ?
    C11 C1 C2 O10 . . . . 167.47(13) ?
    O10 C2 N3 C4 . . . . 0.47(17) ?
    C1 C2 N3 C4 . . . . 178.99(13) ?
    C2 N3 C4 C9 . . . . -0.45(15) ?
    C2 N3 C4 C5 . . . . -179.84(16) ?
    C9 C4 C5 C6 . . . . 1.1(2) ?
    N3 C4 C5 C6 . . . . -179.58(15) ?
    C4 C5 C6 C7 . . . . -0.4(2) ?
    C5 C6 C7 C8 . . . . -0.5(2) ?
    C6 C7 C8 C9 . . . . 0.7(2) ?
    C7 C8 C9 O10 . . . . 179.17(14) ?
    C7 C8 C9 C4 . . . . 0.0(2) ?
    C5 C4 C9 C8 . . . . -1.0(2) ?
    N3 C4 C9 C8 . . . . 179.59(14) ?
    C5 C4 C9 O10 . . . . 179.77(13) ?
    N3 C4 C9 O10 . . . . 0.30(16) ?
    N3 C2 O10 C9 . . . . -0.29(16) ?
    C1 C2 O10 C9 . . . . -178.87(13) ?
    C8 C9 O10 C2 . . . . -179.27(15) ?
    C4 C9 O10 C2 . . . . -0.03(15) ?
    C1 C1 C11 N12 3_566 . . . 75.2(2) ?
    C2 C1 C11 N12 . . . . -102.04(16) ?
    C1 C1 C11 O19 3_566 . . . -102.5(2) ?
    C2 C1 C11 O19 . . . . 80.33(17) ?
    O19 C11 N12 C13 . . . . 1.25(17) ?
    C1 C11 N12 C13 . . . . -176.47(13) ?
    C11 N12 C13 C18 . . . . -0.89(16) ?
    C11 N12 C13 C14 . . . . 178.08(16) ?
    C18 C13 C14 C15 . . . . -0.7(2) ?
    N12 C13 C14 C15 . . . . -179.59(15) ?
    C13 C14 C15 C16 . . . . 0.3(2) ?
    C14 C15 C16 C17 . . . . 0.0(3) ?
    C15 C16 C17 C18 . . . . 0.1(3) ?
    C14 C13 C18 O19 . . . . -178.77(13) ?
    N12 C13 C18 O19 . . . . 0.32(16) ?
    C14 C13 C18 C17 . . . . 0.9(2) ?
    N12 C13 C18 C17 . . . . 180.00(14) ?
    C16 C17 C18 C13 . . . . -0.6(2) ?
    C16 C17 C18 O19 . . . . 179.05(15) ?
    N12 C11 O19 C18 . . . . -1.06(17) ?
    C1 C11 O19 C18 . . . . 176.71(13) ?
    C13 C18 O19 C11 . . . . 0.38(15) ?
    C17 C18 O19 C11 . . . . -179.28(16) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C7 H7 N12 3_567 0.93 2.71 3.348(2) 127
    C17 H17 N3 4_565 0.93 2.71 3.580(2) 153
    C14 H14 N12 3_666 0.93 2.75 3.387(2) 127
data_global
_journal_data_validation_number     ?
_journal_date_recd_electronic     2011-07-01
_journal_date_accepted     2011-07-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      8
_journal_page_first     o2014
_journal_page_last     o2014
_journal_paper_category     QO
_journal_coeditor_code     KP2340
_publ_contact_author_name     'Liliana Dobrza\'nska'
_publ_contact_author_address
;
 Department of Chemistry,
 University of Stellenbosch,
 Private Bag X1, Matieland,
 South Africa
;
_publ_contact_author_email     lianger@sun.ac.za
_publ_contact_author_fax     '+32 16 327 990'
_publ_contact_author_phone     '+32 16 327 423'
_publ_section_title
;
1,1,2,2-Tetrakis(1,3-benzoxazol-2-yl)ethene
;
loop_
    _publ_author_name
    _publ_author_address
    'Tesfamariam K. Hagos'
;
 Department of Chemistry,
 University of Stellenbosch,
 Private Bag X1, Matieland,
 South Africa
;
    'Stefan D. Nogai'
;
 Department of Chemistry,
 University of Stellenbosch,
 Private Bag X1, Matieland,
 South Africa
;
    'Liliana Dobrza\'nska'
;
 Department of Chemistry,
 University of Stellenbosch,
 Private Bag X1, Matieland,
 South Africa
 and
 Department of Chemistry,
 Katholieke Universiteit Leuven,
 Celestijnenlaan 200F - bus 2404,
 B-3001 Heverlee,
 Belgium
;
    'Stephanie Cronje'
;
 Department of Chemistry,
 University of Stellenbosch,
 Private Bag X1, Matieland,
 South Africa
 and
 Institut f\"ur Anorganische und Analytische Chemie,
 Goethe-Universit\"at Frankfurt,
 Max-von-Laue-Strasse 7,
 D-60348 Frankfurt am Main,
 Germany
;
    'Helgard G. Raubenheimer'
;
 Department of Chemistry,
 University of Stellenbosch,
 Private Bag X1, Matieland,
 South Africa
;