##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 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. The current version number is 2.1.    #
#                                                                            #
# 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'by TEXSAN for Windows v1.06/SHELXL97'
_journal_date_recd_electronic     2001-06-21
_journal_date_accepted     2001-07-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2001
_journal_volume     57
_journal_issue      8
_journal_page_first     o695
_journal_page_last     o696
_journal_paper_category     EO
_publ_contact_author_name     'Dr Graham Smith'
_publ_contact_author_address
;
    Centre for Instrumental and Developmental Chemistry
    Queensland University of Technology
    GPO Box 2434, Brisbane 4001, Australia
;
_publ_contact_author_email     g.smith@qut.edu.au
_publ_contact_author_fax     ' 61 7 3864 1804 '
_publ_contact_author_phone     ' 61 7 3864 2293 '
_publ_section_title
;
A phthaloyl-linked benzotriazole corrosion inhibitor:
1,1'-(phthaloyl)bis(benzotriazole)
;
loop_
    _publ_author_name
    _publ_author_address
    'Graham Smith'
;
  Centre for Instrumental and Developmental Chemistry
  Queensland University of Technology
  GPO Box 2434, Brisbane 4001, Australia
;
    'Steven E. Bottle'
;
  Centre for Instrumental and Developmental Chemistry
  Queensland University of Technology
  GPO Box 2434, Brisbane 4001, Australia
;
    'Damien A. Reid'
;
  Centre for Instrumental and Developmental Chemistry
  Queensland University of Technology
  GPO Box 2434, Brisbane 4001, Australia
;
    'D. Paul Schweinsberg'
;
  Centre for Instrumental and Developmental Chemistry
  Queensland University of Technology
  GPO Box 2434, Brisbane 4001, Australia
;
    'Raymond C. Bott'
;
  Centre for Instrumental and Developmental Chemistry
  Queensland University of Technology
  GPO Box 2434, Brisbane 4001, Australia
;
data_I
_audit_creation_method     'SHELXL97 (Sheldrick, 1997) '
_chemical_name_systematic
;
1,1'-(phalolyl)bis(benzotriazole)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H12 N6 O2'
_chemical_formula_sum     'C20 H12 N6 O2'
_chemical_formula_weight     368.36
_chemical_melting_point     '464-466 '
_symmetry_cell_setting     'orthorhombic'
_symmetry_space_group_name_H-M     'P 21 21 21'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     10.744(5)
_cell_length_b     22.193(4)
_cell_length_c     7.079(5)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1687.9(14)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     8.4
_cell_measurement_theta_max     14.7
_cell_measurement_temperature     295(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max      .38
_exptl_crystal_size_mid      .25
_exptl_crystal_size_min      .20
_exptl_crystal_density_diffrn     1.450
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     760
_exptl_absorpt_coefficient_mu      .100
_exptl_absorpt_correction_type     'none'
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71069
_diffrn_radiation_source     'Rigaku rotating anode'
_diffrn_radiation_monochromator     'graphite '
_diffrn_measurement_device_type     'Rigaku AFC-7R '
_diffrn_measurement_method     ω-2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2231
_diffrn_reflns_av_R_equivalents      .0000
_diffrn_reflns_av_sigmaI/netI      .1094
_diffrn_reflns_theta_min     2.11
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     28
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     9
_diffrn_standards_number     3
_diffrn_standards_interval_count     150
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%      .00
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
The absolute configuration could not be determined because of the
composition of the compound and the quantity of data collected.
The lower than desirable reflection-to-parameter ratio (8.78) is considered
acceptable because of the noncentrosymmetric space group (Acta
recommended ratio: 8.0).
;
_reflns_number_total     2231
_reflns_number_gt     992
_reflns_threshold_expression     I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .153
_refine_ls_R_factor_gt      .037
_refine_ls_wR_factor_ref      .138
_refine_ls_goodness_of_fit_ref      .89
_refine_ls_restrained_S_all      .89
_refine_ls_number_reflns     2231
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0638P)²+0.2455P] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean     <0.001
_refine_diff_density_max      .18
_refine_diff_density_min      -.18
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_extinction_coef      .014(2)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N'  .0061  .0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure
Corporation, 1999a)
;
_computing_cell_refinement     'MSC/AFC Diffractometer Control Software '
_computing_data_reduction
;
TEXSAN for Windows (Molecular Structure Corporation, 1999b)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON for Windows (Spek, 1999)'
_computing_publication_material
;
TEXSAN for Windows
;
loop_
    _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
    _atom_site_type_symbol
    O11  .9414(3)  .19130(14)  -.1172(5)  .0514(9) Uani d . 1 . . O
    O21  .6808(3)  .20081(14)  .1940(5)  .0545(9) Uani d . 1 . . O
    N11 1.1388(3)  .17183(15)  -.0238(5)  .0382(9) Uani d . 1 . . N
    N12 1.2205(4)  .16543(19)  .1263(6)  .0514(11) Uani d . 1 . . N
    N13 1.3070(4)  .12837(19)  .0815(6)  .0546(11) Uani d . 1 . . N
    N21  .8174(3)  .12445(15)  .2230(6)  .0419(9) Uani d . 1 . . N
    N22  .9395(3)  .10449(16)  .2440(6)  .0485(10) Uani d . 1 . . N
    N23  .9395(4)  .04697(16)  .2481(6)  .0515(11) Uani d . 1 . . N
    C1 1.0017(4)  .23523(18)  .1734(6)  .0402(11) Uani d . 1 . . C
    C2  .8883(4)  .22956(18)  .2698(6)  .0396(11) Uani d . 1 . . C
    C3  .8648(4)  .2658(2)  .4268(7)  .0473(12) Uani d . 1 . . C
    C4  .9521(5)  .3068(2)  .4859(7)  .0538(13) Uani d . 1 . . C
    C5 1.0631(5)  .3131(2)  .3921(7)  .0520(13) Uani d . 1 . . C
    C6 1.0878(4)  .27723(19)  .2374(7)  .0469(12) Uani d . 1 . . C
    C11 1.0212(4)  .19918(19)  -.0001(7)  .0404(11) Uani d . 1 . . C
    C14 1.2838(4)  .1079(2)  -.1022(7)  .0445(12) Uani d . 1 . . C
    C15 1.3493(4)  .0662(2)  -.2089(7)  .0561(14) Uani d . 1 . . C
    C16 1.3064(5)  .0540(2)  -.3865(8)  .0586(14) Uani d . 1 . . C
    C17 1.2006(5)  .0832(2)  -.4557(7)  .0552(14) Uani d . 1 . . C
    C18 1.1344(4)  .1248(2)  -.3524(7)  .0444(12) Uani d . 1 . . C
    C19 1.1771(4)  .13560(18)  -.1692(6)  .0372(11) Uani d . 1 . . C
    C21  .7875(4)  .1867(2)  .2197(6)  .0415(11) Uani d . 1 . . C
    C24  .8166(4)  .02648(19)  .2318(7)  .0425(11) Uani d . 1 . . C
    C25  .7708(5)  -.0328(2)  .2411(8)  .0559(14) Uani d . 1 . . C
    C26  .6447(5)  -.0393(2)  .2290(8)  .0607(15) Uani d . 1 . . C
    C27  .5663(5)  .0104(2)  .2119(8)  .0595(14) Uani d . 1 . . C
    C28  .6098(4)  .0683(2)  .2031(7)  .0498(12) Uani d . 1 . . C
    C29  .7382(4)  .0754(2)  .2171(6)  .0398(10) Uani d . 1 . . C
    H3  .7882  .2622  .4927  .056 Uiso d . 1 . . H
    H4  .9360  .3313  .5935  .064 Uiso d . 1 . . H
    H5 1.1227  .3418  .4332  .061 Uiso d . 1 . . H
    H6 1.1650  .2814  .1731  .055 Uiso d . 1 . . H
    H15 1.4215  .0469  -.1601  .066 Uiso d . 1 . . H
    H16 1.3488  .0255  -.4633  .069 Uiso d . 1 . . H
    H17 1.1735  .0741  -.5803  .065 Uiso d . 1 . . H
    H18 1.0635  .1448  -.4028  .052 Uiso d . 1 . . H
    H25  .8249  -.0665  .2547  .067 Uiso d . 1 . . H
    H26  .6090  -.0785  .2328  .072 Uiso d . 1 . . H
    H27  .4788  .0040  .2060  .070 Uiso d . 1 . . H
    H28  .5553  .1018  .1880  .059 Uiso d . 1 . . H
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O11 C11 . 1.205(5) ?
    O21 C21 . 1.203(5) ?
    N11 C19 . 1.370(5) ?
    N11 N12 . 1.385(5) ?
    N11 C11 . 1.412(5) ?
    N12 N13 . 1.281(5) ?
    N13 C14 . 1.400(6) ?
    N21 C29 . 1.383(5) ?
    N21 N22 . 1.393(5) ?
    N21 C21 . 1.419(5) ?
    N22 N23 . 1.277(5) ?
    N23 C24 . 1.401(6) ?
    C1 C6 . 1.389(6) ?
    C1 C2 . 1.402(6) ?
    C1 C11 . 1.480(6) ?
    C2 C3 . 1.395(6) ?
    C2 C21 . 1.484(6) ?
    C3 C4 . 1.372(6) ?
    C3 H3 .  .95 ?
    C4 C5 . 1.372(7) ?
    C4 H4 .  .95 ?
    C5 C6 . 1.380(7) ?
    C5 H5 .  .95 ?
    C6 H6 .  .95 ?
    C14 C15 . 1.386(6) ?
    C14 C19 . 1.385(6) ?
    C15 C16 . 1.366(7) ?
    C15 H15 .  .95 ?
    C16 C17 . 1.398(7) ?
    C16 H16 .  .95 ?
    C17 C18 . 1.375(6) ?
    C17 H17 .  .95 ?
    C18 C19 . 1.396(6) ?
    C18 H18 .  .95 ?
    C24 C29 . 1.378(6) ?
    C24 C25 . 1.407(6) ?
    C25 C26 . 1.365(8) ?
    C25 H25 .  .95 ?
    C26 C27 . 1.392(7) ?
    C26 H26 .  .95 ?
    C27 C28 . 1.368(6) ?
    C27 H27 .  .95 ?
    C28 C29 . 1.392(6) ?
    C28 H28 .  .95 ?
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
    C19 N11 N12 . . 109.0(3) ?
    C19 N11 C11 . . 127.6(4) ?
    N12 N11 C11 . . 121.3(4) ?
    N13 N12 N11 . . 109.6(4) ?
    N12 N13 C14 . . 108.1(4) ?
    C29 N21 N22 . . 109.4(3) ?
    C29 N21 C21 . . 128.9(3) ?
    N22 N21 C21 . . 121.6(3) ?
    N23 N22 N21 . . 108.7(4) ?
    N22 N23 C24 . . 108.8(4) ?
    C6 C1 C2 . . 118.7(4) ?
    C6 C1 C11 . . 122.6(4) ?
    C2 C1 C11 . . 118.6(4) ?
    C3 C2 C1 . . 119.6(4) ?
    C3 C2 C21 . . 115.3(4) ?
    C1 C2 C21 . . 125.1(4) ?
    C4 C3 C2 . . 120.1(4) ?
    C4 C3 H3 . . 120 ?
    C2 C3 H3 . . 120 ?
    C5 C4 C3 . . 120.9(5) ?
    C5 C4 H4 . . 119 ?
    C3 C4 H4 . . 120 ?
    C4 C5 C6 . . 119.5(5) ?
    C4 C5 H5 . . 120 ?
    C6 C5 H5 . . 120 ?
    C5 C6 C1 . . 121.2(5) ?
    C5 C6 H6 . . 120 ?
    C1 C6 H6 . . 119 ?
    O11 C11 N11 . . 119.5(4) ?
    O11 C11 C1 . . 123.3(4) ?
    N11 C11 C1 . . 117.2(4) ?
    C15 C14 C19 . . 122.0(5) ?
    C15 C14 N13 . . 129.3(5) ?
    C19 C14 N13 . . 108.7(4) ?
    C16 C15 C14 . . 117.5(5) ?
    C16 C15 H15 . . 121 ?
    C14 C15 H15 . . 121 ?
    C15 C16 C17 . . 120.3(5) ?
    C15 C16 H16 . . 120 ?
    C17 C16 H16 . . 120 ?
    C18 C17 C16 . . 123.1(5) ?
    C18 C17 H17 . . 119 ?
    C16 C17 H17 . . 118 ?
    C17 C18 C19 . . 116.1(4) ?
    C17 C18 H18 . . 122 ?
    C19 C18 H18 . . 122 ?
    N11 C19 C14 . . 104.6(4) ?
    N11 C19 C18 . . 134.4(4) ?
    C14 C19 C18 . . 120.9(4) ?
    O21 C21 N21 . . 118.1(4) ?
    O21 C21 C2 . . 124.4(4) ?
    N21 C21 C2 . . 117.1(4) ?
    C29 C24 N23 . . 109.1(4) ?
    C29 C24 C25 . . 121.7(5) ?
    N23 C24 C25 . . 129.0(4) ?
    C26 C25 C24 . . 116.2(5) ?
    C26 C25 H25 . . 122 ?
    C24 C25 H25 . . 122 ?
    C25 C26 C27 . . 121.5(5) ?
    C25 C26 H26 . . 120 ?
    C27 C26 H26 . . 119 ?
    C28 C27 C26 . . 122.8(5) ?
    C28 C27 H27 . . 119 ?
    C26 C27 H27 . . 119 ?
    C27 C28 C29 . . 116.2(5) ?
    C27 C28 H28 . . 122 ?
    C29 C28 H28 . . 122 ?
    C24 C29 N21 . . 104.0(3) ?
    C24 C29 C28 . . 121.5(4) ?
    N21 C29 C28 . . 134.5(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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C19 N11 N12 N13 . . . .  .8(5) ?
    C11 N11 N12 N13 . . . . 165.9(4) ?
    N11 N12 N13 C14 . . . . -1.0(5) ?
    C29 N21 N22 N23 . . . . 1.0(6) ?
    C21 N21 N22 N23 . . . . 178.0(4) ?
    N21 N22 N23 C24 . . . .  -.5(6) ?
    C6 C1 C2 C3 . . . .  -.1(6) ?
    C11 C1 C2 C3 . . . . -176.0(4) ?
    C6 C1 C2 C21 . . . . -179.7(4) ?
    C11 C1 C2 C21 . . . . 4.4(6) ?
    C1 C2 C3 C4 . . . .  .2(6) ?
    C21 C2 C3 C4 . . . . 179.7(4) ?
    C2 C3 C4 C5 . . . .  .2(7) ?
    C3 C4 C5 C6 . . . .  -.6(7) ?
    C4 C5 C6 C1 . . . .  .6(7) ?
    C2 C1 C6 C5 . . . .  -.3(7) ?
    C11 C1 C6 C5 . . . . 175.5(4) ?
    C19 N11 C11 O11 . . . .  .0(7) ?
    N12 N11 C11 O11 . . . . -162.0(4) ?
    C19 N11 C11 C1 . . . . 178.4(4) ?
    N12 N11 C11 C1 . . . . 16.3(6) ?
    C6 C1 C11 O11 . . . . -135.2(5) ?
    C2 C1 C11 O11 . . . . 40.6(6) ?
    C6 C1 C11 N11 . . . . 46.5(6) ?
    C2 C1 C11 N11 . . . . -137.7(4) ?
    N12 N13 C14 C15 . . . . -178.0(5) ?
    N12 N13 C14 C19 . . . .  .8(5) ?
    C19 C14 C15 C16 . . . . 1.4(7) ?
    N13 C14 C15 C16 . . . . 179.9(5) ?
    C14 C15 C16 C17 . . . .  .3(7) ?
    C15 C16 C17 C18 . . . .  -.2(8) ?
    C16 C17 C18 C19 . . . . -1.6(7) ?
    N12 N11 C19 C14 . . . .  -.3(5) ?
    C11 N11 C19 C14 . . . . -164.2(4) ?
    N12 N11 C19 C18 . . . . -178.1(4) ?
    C11 N11 C19 C18 . . . . 18.1(8) ?
    C15 C14 C19 N11 . . . . 178.6(4) ?
    N13 C14 C19 N11 . . . .  -.2(5) ?
    C15 C14 C19 C18 . . . . -3.3(7) ?
    N13 C14 C19 C18 . . . . 177.9(4) ?
    C17 C18 C19 N11 . . . . -179.3(5) ?
    C17 C18 C19 C14 . . . . 3.2(6) ?
    C29 N21 C21 O21 . . . . -6.3(7) ?
    N22 N21 C21 O21 . . . . 177.2(4) ?
    C29 N21 C21 C2 . . . . 166.9(4) ?
    N22 N21 C21 C2 . . . . -9.5(6) ?
    C3 C2 C21 O21 . . . . 53.4(6) ?
    C1 C2 C21 O21 . . . . -127.0(5) ?
    C3 C2 C21 N21 . . . . -119.4(4) ?
    C1 C2 C21 N21 . . . . 60.2(6) ?
    N22 N23 C24 C29 . . . .  -.1(6) ?
    N22 N23 C24 C25 . . . . -175.7(5) ?
    C29 C24 C25 C26 . . . . 1.9(8) ?
    N23 C24 C25 C26 . . . . 177.0(6) ?
    C24 C25 C26 C27 . . . . -1.1(9) ?
    C25 C26 C27 C28 . . . . 1.0(9) ?
    C26 C27 C28 C29 . . . . -1.5(8) ?
    N23 C24 C29 N21 . . . .  .6(5) ?
    C25 C24 C29 N21 . . . . 176.6(5) ?
    N23 C24 C29 C28 . . . . -178.6(5) ?
    C25 C24 C29 C28 . . . . -2.6(8) ?
    N22 N21 C29 C24 . . . . -1.0(5) ?
    C21 N21 C29 C24 . . . . -177.7(4) ?
    N22 N21 C29 C28 . . . . 178.1(5) ?
    C21 N21 C29 C28 . . . . 1.3(9) ?
    C27 C28 C29 C24 . . . . 2.3(8) ?
    C27 C28 C29 N21 . . . . -176.6(5) ?
