#\#CIF_1.1
 
#  CIF produced by WinGX routine CIF_UPDATE
#  Created on 2009-09-10 at 15:41:42
#  Using CIFtbx version 2.6.2 16 Jun 1998
 
#  Dictionary name : cif_core.dic
#  Dictionary vers : 2.3
#  Request file    : c:\program files\wingx\files\cifdoc.dat
#  CIF files read  : kln1-4 dreduc struct
 
#------------------ SECTION 1. GLOBAL INFORMATION ---------------------------#
 
data_global
 
#------------------ AUDIT DETAILS -------------------------------------------#
 
_audit_creation_date            2009-09-10
_audit_creation_method          'WinGX routine CIF_UPDATE'
_audit_conform_dict_name        cif_core.dic
_audit_conform_dict_version     2.3
_audit_conform_dict_location    ftp://ftp.iucr.org/pub/cif_core.dic
_audit_update_record            ?
 
#------------------ SUBMISSION DETAILS --------------------------------------#
 
# Name and address of author for correspondence
 
_publ_contact_author_name      'Mol\<canov, Kre\<simir'
_publ_contact_author_address
;
Division of Physical Chemistry
Rudjer Bo\<skovi\'c Institute
Bijeni\<cka cesta 50
HR-10000 Zagreb
Croatia
;
_publ_contact_author_email       kmolcano@irb.hr
_publ_contact_author_fax         ?
_publ_contact_author_phone       ?
 
_publ_requested_journal          'J. Med. Chem.'
_publ_requested_coeditor_name    ?
_publ_contact_letter            # Include date of submission
;
Date of submission ?
 
Please consider this CIF submission for publication in
J. Med. Chem.
;
_publ_requested_category        ?
 
#------------------ PROCESSING SUMMARY (JOURNAL OFFICE ONLY) ----------------#
 
_journal_date_recd_electronic    ?
_journal_date_to_coeditor        ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?
_journal_date_printers_first     ?
_journal_date_printers_final     ?
_journal_date_proofs_out         ?
_journal_date_proofs_in          ?
_journal_coeditor_name           ?
_journal_coeditor_code           ?
_journal_coeditor_notes          ?
_journal_techeditor_code         ?
_journal_techeditor_notes        ?
_journal_coden_ASTM              ?
_journal_name_full               ?
_journal_year                    ?
_journal_volume                  ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?
_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?
 
#------------------ TITLE AND AUTHOR LIST------------------------------------#
 
_publ_section_title
;
 Synthesis and Evaluation of 4-Nitro- Substituted 1,3-Diaryltriazenes as 
a Novel Class of Potent Antitumor Agents
;
 
_publ_section_title_footnote
;
?
;
 
loop_
_publ_author_name
_publ_author_address
'\<Cimbora-Zovko, Tamara'
;
Division of Molecular Biology
Rudjer Bo\<skovi\'c Institute
Bijeni\<cka cesta 50
HR-10000 Zagreb
Croatia
;

'Brozovi\'c, Anamaria'
;
Division of Molecular Biology
Rudjer Bo\<skovi\'c Institute
Bijeni\<cka cesta 50
HR-10000 Zagreb
Croatia
;

'Mol\<canov, Kre\<simir'
;
Division of Physical Chemistry
Rudjer Bo\<skovi\'c Institute
Bijeni\<cka cesta 50
HR-10000 Zagreb
Croatia
;

'Koji\'c-Prodi\'c, Biserka'
;
Division of Physical Chemistry
Rudjer Bo\<skovi\'c Institute
Bijeni\<cka cesta 50
HR-10000 Zagreb
Croatia
;

'Piantanida, Ivo'
;
Division of Organic Chemistry and Biochemistry
Rudjer Bo\<skovi\'c Institute
Bijeni\<cka cesta 50
HR-10000 Zagreb
Croatia
;

'Fritz, Gerhard'
;
Institute of Toxicology
University of Mainz
Obere Zalbacher Str. 67
D-55131 Mainz
Germany
;

'Virag, Andrej'
;
Faculty of Chemistry and Chemical Technology
University of Ljubljana
A\<sker\<ceva 5
SI-1000 Ljubljana
Slovenia
;

'Ali\<c, Branko'
;
Faculty of Chemistry and Chemical Technology
University of Ljubljana
A\<sker\<ceva 5
SI-1000 Ljubljana
Slovenia
;

'Ko\<cevar, Marijan'
;
Faculty of Chemistry and Chemical Technology
University of Ljubljana
A\<sker\<ceva 5
SI-1000 Ljubljana
Slovenia
;
 
'Polanc, Slovenko'
;
Faculty of Chemistry and Chemical Technology
University of Ljubljana
A\<sker\<ceva 5
SI-1000 Ljubljana
Slovenia
;
'Osmak, Maja'
;
Division of Molecular Biology
Rudjer Bo\<skovi\'c Institute
Bijeni\<cka cesta 50
HR-10000 Zagreb
Croatia
;

#------------------ TEXT ----------------------------------------------------#
 
_publ_section_synopsis
;
# Insert blank lines between paragraphs
?
;
_publ_section_abstract
;
# Insert blank lines between paragraphs
 ?
;
 
_publ_section_comment
;
# Insert blank lines between paragraphs
 ?
;
 
_publ_section_exptl_prep
;
 ?
;
 
_publ_section_exptl_refinement
;
 ?
;
 
# Insert blank lines between references
 
_publ_section_references
;
 Allen, F.H., Kennard, O. & Taylor, R. (1983).
   Acc. Chem. Res.  16, 146-153.
 
 Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A.
   (1993) J. Appl. Cryst. 26, 343-350.
 
 Altomare, A. Burla, M. C., Camalli, M., Cascarano, G. L.,
 Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G.
 & Spagna, R. (1999) J. Appl. Cryst. 32, 115-119.
 
 Blessing, R. H. (1995) Acta Cryst., A51, 33-38.
 
 Blessing, R. H. (1987) Cryst. Rev. 1, 3-58.
 
 Blessing, R. H. (1989) J. Appl. Cryst. 22, 396-397.
 
 Beurskens, P.T., Beurskens, G., de Gelder, R.,
   Garci\'ia-Granda, S., Gould, R.O., Israel, R. & Smits, J.M.M.
   (1999) The DIRDIF-99 program system,
   Technical Report of the Crystallography Laboratory,
   University of Nijmegen, The Netherlands.
 
 Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
 
 Enraf-Nonius (1994). CAD4Express Software. Enraf-Nonius, Delft,
   The Netherlands.
 
 Farrugia, L. J. (1997) ORTEP-3 for Windows, J. Appl. Cryst. 30, 565.
 
 Farrugia, L. J. (1999) WinGX, J. Appl. Cryst. 32, 837-838.
 
 Flack, H.D. (1983). Acta Cryst. A39, 876-881.
 
 Harms, K. & Wocadlo, S. (1995) XCAD-4. Program for Processing CAD-4
 Diffractometer Data. University of Marburg, Germany.
 
 Johnson, C.K. (1965). ORTEP. Report ORNL-3794. Oak Ridge National
 Laboratory, Tennessee, USA.
 
 Lehman, M. S. and Larsen, F. K. (1974) Acta. Cryst. A30, 580
 
 LePage, Y. (1987). J. Appl. Cryst. 20, 264-269.
 
 North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968) Acta Cryst,
 A24, 351-359
 
 Orpen, A. G., Brammer, L., Allen, F. H., Kennard, O., Watson, D. G.,
 & Taylor, R. (1992). International Tables for Crystallography,
 Volume C.
 
 Sheldrick, G.M. (1993) SHELXL93. Program for crystal structure
   refinement. University of G\"ottingen, Germany.
 
 Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure
   refinement. University of G\"ottingen, Germany.
 
 Sheldrick, G.M. (1985). SHELXS86. In Crystallographic Computing 3,
 edited by G. M. Sheldrick, C. Kruger & R. Goddard, pp. 175-189.
 Oxford University Press.
 
 Sheldrick, G.M. (1997) SHELXS97. Program for Crystal Structure solution.
   University of G\"ottingen, Germany.
 
 Spek, A.L. (1990). Acta Cryst. A46, C34
 
 Streltsov, V. A. & Zavodnik, V. E. (1989) Sov. Phys. Crystallogr.
 34, 824-828
 
 Streltsov, V. A. & Zavodnik, V. E. (1990) Sov. Phys. Crystallogr.
 35, 281.
 
 Walker, N. &  Stuart, D. (1983). Acta Cryst., A39, 158 - 166.
 
 Wilson, A.J.C. (1992) Ed. International Tables for Crystallography,
   Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;
_publ_section_figure_captions
;
 Figure 1. View of (I) (50% probability displacement ellipsoids)
;
_publ_section_acknowledgements
;
 ?
;
_publ_section_table_legends
;
Table 1. Fractional atomic coordinates and equivalent
         isotropic displacement parameters (\%A^2^)
 
Table 2. Selected geometric parameters (\%A ,\% )
;
 
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#
 
data_8b
 
_audit_creation_date                    2009-09-10T15:41:42-00:00
_audit_creation_method                  'WinGX routine CIF_UPDATE'
 
#------------------ CHEMICAL INFORMATION ------------------------------------#
 
_chemical_formula_moiety                'C14 H9 Cl2 N5 O5'
_chemical_formula_sum                   'C14 H9 Cl2 N5 O5'
_chemical_formula_weight                398.16
_chemical_absolute_configuration        unk
_chemical_name_systematic		3-acetyl-1,3-bis(2-chloro-4-nitrophenyl)-1-triazene
 
#------------------ UNIT CELL INFORMATION -----------------------------------#
 
_symmetry_cell_setting                  orthorhombic
_symmetry_space_group_name_H-M          'P b c 21'
_symmetry_space_group_name_Hall		'P 2c -2b'
loop_
    _symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, z'
'x, -y+1/2, z+1/2'
 
_cell_length_a                          7.1152(5)
_cell_length_b                          16.3138(7)
_cell_length_c                          28.6832(19)
_cell_angle_alpha                       90
_cell_angle_beta                        90
_cell_angle_gamma                       90
_cell_volume                            3329.4(4)
_cell_formula_units_Z                   8
_cell_measurement_temperature           293(2)
_cell_measurement_reflns_used           25
_cell_measurement_theta_min             10.3
_cell_measurement_theta_max             15.8
 
#------------------ CRYSTAL INFORMATION -------------------------------------#
 
_exptl_crystal_description              rod
_exptl_crystal_colour                   'pale yellow'
_exptl_crystal_size_max                 0.4
_exptl_crystal_size_mid                 0.09
_exptl_crystal_size_min                 0.07
_exptl_crystal_density_diffrn           1.589
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    1616
_exptl_absorpt_coefficient_mu           3.876
_exptl_absorpt_correction_type          none
 
#------------------ DATA COLLECTION INFORMATION -----------------------------#
 
_diffrn_radiation_wavelength            1.54184
_diffrn_radiation_type                  CuK\a
_diffrn_radiation_probe                 x-ray
_diffrn_ambient_temperature 		    293(2)
_diffrn_measurement_device_type         'Enraf Nonius CAD4'
_diffrn_measurement_device              '\k-geometry diffractometer'
_diffrn_measurement_method              'non-profiled omega/2theta scans'
_diffrn_standards_number                3
_diffrn_standards_interval_time         120
_diffrn_standards_decay_%               1
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
2 1 -2
0 2 8
2 -1 -2
 
_diffrn_reflns_number                   3555
_diffrn_reflns_av_R_equivalents         0
_diffrn_reflns_limit_h_min              0
_diffrn_reflns_limit_h_max              8
_diffrn_reflns_limit_k_min              0
_diffrn_reflns_limit_k_max              20
_diffrn_reflns_limit_l_min              -36
_diffrn_reflns_limit_l_max              0
_diffrn_reflns_theta_min                3.08
_diffrn_reflns_theta_max                76.32
_diffrn_reflns_theta_full               76.32
_diffrn_measured_fraction_theta_max
                                        0.998
_diffrn_measured_fraction_theta_full
                                        0.998
_reflns_number_total                    3555
_reflns_number_gt                       2010
_reflns_threshold_expression            >2sigma(I)
 
#------------------ COMPUTER PROGRAMS USED ----------------------------------#
 
_computing_data_collection              'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement              'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction               'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution           'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics           'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
                                   'WinGX publication routines (Farrugia, 1999)'
 
#------------------ REFINEMENT INFORMATION ----------------------------------#
 
_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^)+(0.1050P)^2^+0.7611P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment           constr
_refine_ls_extinction_method            SHELXL
_refine_ls_extinction_expression
                                    Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_coef              0.0009(2)
_refine_ls_number_reflns                3555
_refine_ls_number_parameters            489
_refine_ls_number_restraints            4
_refine_ls_R_factor_gt                  0.0634
_refine_ls_wR_factor_ref                0.2009
_refine_ls_goodness_of_fit_ref          1.033
_refine_ls_restrained_S_all             1.034
_refine_ls_shift/su_max                 0.013
_refine_ls_abs_structure_details
                                    'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack          0.06(4)
_refine_diff_density_max                0.357
_refine_diff_density_min                -0.205
 
#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#
 
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
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_calc_flag
    _atom_site_refinement_flags
    _atom_site_disorder_group
    _atom_site_disorder_assembly
C2A C 0.798(2) 0.0774(8) 0.2985(5) 0.109(5) Uani 1 d . . A
H2A H 0.7666 0.0282 0.2841 0.13 Uiso 1 calc R . .
C1A C 0.961(2) 0.0822(8) 0.3194(5) 0.086(3) Uani 1 d . . .
C6A C 1.0109(18) 0.1465(10) 0.3422(5) 0.092(4) Uani 1 d . . A
H6A H 1.1244 0.1467 0.3583 0.111 Uiso 1 calc R . .
Cl1A Cl 0.4795(11) 0.1340(4) 0.2736(3) 0.085(3) Uani 0.403(5) d P 1 A
Cl1B Cl 1.0333(15) 0.1189(5) 0.0472(4) 0.106(3) Uani 0.403(5) d P 1 A
Cl2A Cl 0.9196(9) 0.3011(4) 0.3763(2) 0.126(2) Uani 0.597(5) d P 2 A
Cl2B Cl 0.6014(6) -0.0517(2) -0.05721(16) 0.0754(12) Uani 0.597(5) d P 2 A
C4A C 0.725(2) 0.2150(6) 0.3200(4) 0.080(3) Uani 1 d . . A
C5A C 0.8910(19) 0.2193(7) 0.3430(4) 0.094(4) Uani 1 d . . .
C3A C 0.669(2) 0.1419(7) 0.2964(5) 0.113(5) Uani 1 d . . .
Cl3A Cl 0.6463(4) 0.22230(11) 0.15627(10) 0.0748(7) Uani 1 d . . .
Cl3B Cl 0.8518(4) 0.03019(12) 0.15921(11) 0.0771(7) Uani 1 d . . .
C9B C 0.8480(12) -0.1249(5) 0.1882(4) 0.057(2) Uani 1 d . . .
H9B H 0.8424 -0.1026 0.218 0.069 Uiso 1 calc R . .
C8B C 0.8532(11) -0.0756(4) 0.1505(3) 0.055(2) Uani 1 d . . .
N5A N 0.6403(12) 0.5134(5) 0.0895(3) 0.072(2) Uani 1 d . . .
C12A C 0.6516(13) 0.4449(5) 0.2127(3) 0.059(2) Uani 1 d . . .
H15A H 0.6551 0.4673 0.2425 0.071 Uiso 1 calc R . .
N5B N 0.8495(13) -0.2628(5) 0.2235(3) 0.073(2) Uani 1 d . . .
C8A C 0.6517(12) 0.3275(5) 0.1628(3) 0.058(2) Uani 1 d . . .
C9A C 0.6415(12) 0.3768(5) 0.1230(4) 0.059(2) Uani 1 d . . .
H9A H 0.635 0.3543 0.0932 0.07 Uiso 1 calc R . .
N4B N 0.8463(11) -0.0542(4) 0.0670(3) 0.0638(19) Uani 1 d . . .
C12B C 0.8566(12) -0.1935(5) 0.1006(3) 0.062(2) Uani 1 d . . .
H12B H 0.8554 -0.2164 0.0709 0.075 Uiso 1 calc R . .
C10A C 0.6415(12) 0.4613(5) 0.1302(3) 0.055(2) Uani 1 d . . .
C11B C 0.8597(12) -0.2431(5) 0.1391(3) 0.058(2) Uani 1 d . . .
H11B H 0.8677 -0.2997 0.1359 0.069 Uiso 1 calc R . .
C7A C 0.6520(12) 0.3603(5) 0.2077(3) 0.056(2) Uani 1 d . . .
C10B C 0.8510(12) -0.2085(5) 0.1821(3) 0.055(2) Uani 1 d . . .
C7B C 0.8553(12) -0.1076(5) 0.1060(3) 0.054(2) Uani 1 d . . .
N4A N 0.6718(11) 0.3057(4) 0.2455(3) 0.063(2) Uani 1 d . . .
C11A C 0.6460(13) 0.4965(5) 0.1749(3) 0.060(2) Uani 1 d . . .
H11A H 0.6451 0.5531 0.1788 0.072 Uiso 1 calc R . .
O3A O 0.6414(12) 0.4833(5) 0.0513(3) 0.095(2) Uani 1 d . . .
O4A O 0.6409(16) 0.5867(4) 0.0951(3) 0.120(4) Uani 1 d . . .
O3B O 0.8321(13) -0.2294(5) 0.2613(3) 0.099(3) Uani 1 d . . .
N3B N 0.9492(12) -0.0782(5) 0.0342(3) 0.062(2) Uani 1 d . . A
O4B O 0.8633(14) -0.3359(5) 0.2171(3) 0.109(3) Uani 1 d . . .
C4B C 0.8109(14) 0.0407(6) -0.0056(3) 0.067(2) Uani 1 d . . A
C3B C 0.8570(16) 0.1130(6) 0.0180(4) 0.077(3) Uani 1 d . . .
O5B O 1.0598(12) -0.0001(6) -0.0739(3) 0.090(2) Uani 1 d . . .
N2B N 0.9402(13) -0.0282(5) -0.0048(3) 0.072(2) Uani 1 d . . .
N2A N 0.6039(13) 0.2826(5) 0.3177(3) 0.073(2) Uani 1 d . . .
C1B C 0.5686(18) 0.1673(7) -0.0019(4) 0.075(3) Uani 1 d . . .
N3A N 0.5847(11) 0.3307(4) 0.2799(3) 0.0623(19) Uani 1 d . . A
C13B C 1.0520(17) -0.0468(7) -0.0417(4) 0.072(3) Uani 1 d . . A
C6B C 0.5202(19) 0.0924(9) -0.0269(5) 0.086(4) Uani 1 d . . A
H6B H 0.4037 0.0865 -0.0412 0.103 Uiso 1 calc R . .
O2B O 0.4714(16) 0.2945(6) 0.0215(4) 0.114(3) Uani 1 d . . .
C5B C 0.6452(16) 0.0339(6) -0.0285(3) 0.069(3) Uani 1 d . . .
C14B C 1.1490(17) -0.1280(7) -0.0408(4) 0.087(3) Uani 1 d . . .
H14D H 1.1231 -0.1549 -0.0117 0.13 Uiso 1 calc R . A
H14E H 1.2821 -0.12 -0.0439 0.13 Uiso 1 calc R . .
H14F H 1.1041 -0.1613 -0.066 0.13 Uiso 1 calc R . .
C2B C 0.7319(18) 0.1766(7) 0.0205(4) 0.078(3) Uani 1 d . . A
H2B H 0.7593 0.2241 0.037 0.094 Uiso 1 calc R . .
C13A C 0.4863(16) 0.3018(7) 0.3574(5) 0.079(3) Uani 1 d . . A
N1B N 0.4240(17) 0.2343(7) 0.0021(4) 0.085(3) Uani 1 d . . A
O5A O 0.4976(14) 0.2548(7) 0.3908(3) 0.113(3) Uani 1 d . . .
C14A C 0.3645(16) 0.3755(7) 0.3542(4) 0.090(3) Uani 1 d . . .
H14B H 0.3817 0.4012 0.3244 0.135 Uiso 1 calc R . A
H14C H 0.3978 0.4134 0.3784 0.135 Uiso 1 calc R . .
H14A H 0.2354 0.3597 0.3577 0.135 Uiso 1 calc R . .
O2A O 1.0320(19) -0.0531(8) 0.2999(6) 0.169(6) Uani 1 d U . .
N1A N 1.095(2) 0.0093(10) 0.3196(5) 0.131(5) Uani 1 d U . .
O1A O 1.240(2) 0.0249(10) 0.3366(5) 0.175(6) Uani 1 d U . .
O1B O 0.2705(13) 0.2209(6) -0.0127(4) 0.118(3) Uani 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
C2A 0.157(13) 0.076(8) 0.093(9) 0.007(7) 0.050(10) 0.018(9)
C1A 0.110(10) 0.069(7) 0.078(8) -0.006(6) 0.016(7) 0.028(7)
C6A 0.098(9) 0.115(11) 0.064(8) 0.034(8) 0.016(6) 0.003(7)
Cl1A 0.098(5) 0.048(3) 0.109(6) -0.007(4) -0.034(4) -0.015(3)
Cl1B 0.136(7) 0.081(5) 0.100(6) -0.008(4) -0.020(5) -0.025(5)
Cl2A 0.133(5) 0.122(5) 0.124(5) 0.008(4) -0.019(4) -0.025(4)
Cl2B 0.073(3) 0.068(2) 0.085(3) -0.014(2) -0.004(2) -0.0132(19)
C4A 0.127(9) 0.055(5) 0.056(6) 0.012(4) 0.022(7) 0.015(6)
C5A 0.120(10) 0.097(8) 0.065(7) 0.011(6) 0.004(7) 0.008(8)
C3A 0.190(16) 0.067(6) 0.080(8) 0.029(6) 0.044(9) 0.039(9)
Cl3A 0.0890(15) 0.0459(9) 0.0894(16) -0.0087(12) 0.0031(15) 0.0001(11)
Cl3B 0.0892(15) 0.0465(9) 0.0956(17) -0.0123(12) 0.0049(16) 0.0018(11)
C9B 0.052(5) 0.058(5) 0.062(5) -0.005(4) -0.002(4) 0.011(4)
C8B 0.050(4) 0.045(3) 0.069(6) -0.014(4) -0.007(4) 0.006(4)
N5A 0.094(6) 0.061(4) 0.060(5) 0.009(4) -0.008(5) 0.011(4)
C12A 0.072(6) 0.054(4) 0.051(5) -0.009(4) -0.002(4) -0.001(4)
N5B 0.090(6) 0.065(5) 0.064(6) 0.002(4) -0.002(5) 0.010(5)
C8A 0.055(5) 0.057(4) 0.061(5) 0.000(4) -0.002(4) -0.001(4)
C9A 0.055(5) 0.058(5) 0.063(5) -0.008(4) 0.008(4) 0.001(4)
N4B 0.071(5) 0.058(4) 0.062(5) 0.007(4) -0.010(4) 0.007(4)
C12B 0.061(6) 0.058(5) 0.067(6) -0.006(4) -0.010(5) 0.004(5)
C10A 0.057(5) 0.050(4) 0.059(5) 0.003(4) -0.013(4) 0.002(4)
C11B 0.069(5) 0.044(4) 0.059(5) 0.000(4) -0.002(4) 0.002(4)
C7A 0.053(5) 0.057(5) 0.058(5) -0.007(4) -0.009(4) 0.000(4)
C10B 0.061(5) 0.051(4) 0.054(5) 0.006(4) 0.005(4) 0.006(4)
C7B 0.053(5) 0.046(4) 0.064(6) 0.004(4) 0.003(4) 0.002(4)
N4A 0.078(5) 0.058(4) 0.053(4) -0.002(3) -0.001(4) -0.004(4)
C11A 0.069(6) 0.046(4) 0.066(6) -0.009(4) -0.004(5) -0.003(4)
O3A 0.136(7) 0.089(5) 0.061(4) -0.002(4) -0.008(5) 0.029(5)
O4A 0.227(12) 0.056(4) 0.077(5) 0.006(4) -0.030(6) 0.025(6)
O3B 0.133(7) 0.101(6) 0.061(5) 0.004(4) 0.010(5) 0.017(5)
N3B 0.072(5) 0.052(4) 0.063(5) 0.002(4) -0.010(4) -0.004(4)
O4B 0.172(9) 0.066(5) 0.089(5) 0.024(4) 0.002(6) 0.007(5)
C4B 0.071(6) 0.072(6) 0.059(5) 0.011(4) -0.010(5) 0.004(5)
C3B 0.086(7) 0.066(6) 0.079(7) -0.002(5) -0.010(6) -0.002(6)
O5B 0.106(6) 0.097(6) 0.067(5) 0.011(5) 0.007(4) -0.007(5)
N2B 0.082(5) 0.064(5) 0.071(5) 0.006(4) -0.002(5) 0.007(4)
N2A 0.106(6) 0.062(4) 0.052(4) -0.001(4) 0.009(5) 0.012(5)
C1B 0.086(7) 0.082(7) 0.057(6) 0.022(5) 0.023(6) 0.007(6)
N3A 0.066(5) 0.058(4) 0.063(5) 0.008(4) 0.002(4) -0.012(4)
C13B 0.091(7) 0.077(7) 0.047(6) 0.004(5) 0.005(5) -0.013(6)
C6B 0.107(9) 0.095(10) 0.057(7) 0.010(7) 0.001(6) -0.004(7)
O2B 0.151(9) 0.081(6) 0.109(7) -0.003(6) 0.019(6) 0.013(6)
C5B 0.093(8) 0.067(6) 0.047(5) 0.006(4) 0.013(5) -0.003(6)
C14B 0.091(8) 0.090(7) 0.078(7) 0.001(6) -0.013(6) 0.021(6)
C2B 0.094(8) 0.077(7) 0.063(6) 0.005(5) -0.018(6) -0.009(6)
C13A 0.095(8) 0.062(6) 0.079(8) -0.010(6) -0.005(6) 0.002(5)
N1B 0.090(7) 0.083(7) 0.083(7) 0.015(5) 0.012(6) 0.010(6)
O5A 0.164(8) 0.100(6) 0.077(6) -0.001(6) 0.028(5) 0.016(6)
C14A 0.097(8) 0.096(7) 0.078(7) -0.027(6) 0.011(6) 0.010(6)
O2A 0.161(10) 0.119(9) 0.229(16) -0.043(10) 0.044(10) 0.034(7)
N1A 0.167(12) 0.128(10) 0.097(9) -0.017(8) 0.062(9) -0.002(11)
O1A 0.148(11) 0.211(14) 0.168(13) 0.023(10) -0.008(10) 0.039(10)
O1B 0.081(5) 0.124(7) 0.151(8) 0.014(6) 0.001(6) 0.022(5)
 
 
#------------------ MOLECULAR GEOMETRY --------------------------------------#
 
_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
C2A C1A 1.31(2) . ?
C2A C3A 1.397(18) . ?
C2A H2A 0.93 . ?
C1A C6A 1.286(19) . ?
C1A N1A 1.52(2) . ?
C6A C5A 1.463(19) . ?
C6A H6A 0.93 . ?
Cl1A C3A 1.507(19) . ?
Cl1B C3B 1.512(14) . ?
Cl2A C5A 1.653(14) . ?
Cl2B C5B 1.650(10) . ?
C4A C5A 1.358(17) . ?
C4A N2A 1.399(13) . ?
C4A C3A 1.426(18) . ?
Cl3A C8A 1.727(9) . ?
Cl3B C8B 1.745(7) . ?
C9B C8B 1.348(13) . ?
C9B C10B 1.376(12) . ?
C9B H9B 0.93 . ?
C8B C7B 1.377(13) . ?
N5A O3A 1.203(11) . ?
N5A O4A 1.206(10) . ?
N5A C10A 1.443(11) . ?
C12A C11A 1.375(12) . ?
C12A C7A 1.387(11) . ?
C12A H15A 0.93 . ?
N5B O4B 1.211(10) . ?
N5B O3B 1.221(11) . ?
N5B C10B 1.480(12) . ?
C8A C7A 1.393(12) . ?
C8A C9A 1.399(13) . ?
C9A C10A 1.395(11) . ?
C9A H9A 0.93 . ?
N4B N3B 1.254(10) . ?
N4B C7B 1.421(11) . ?
C12B C11B 1.370(12) . ?
C12B C7B 1.410(11) . ?
C12B H12B 0.93 . ?
C10A C11A 1.405(12) . ?
C11B C10B 1.357(12) . ?
C11B H11B 0.93 . ?
C7A N4A 1.409(11) . ?
N4A N3A 1.235(10) . ?
C11A H11A 0.93 . ?
N3B N2B 1.387(11) . ?
C4B C5B 1.355(14) . ?
C4B C3B 1.398(14) . ?
C4B N2B 1.452(12) . ?
C3B C2B 1.368(15) . ?
O5B C13B 1.197(12) . ?
N2B C13B 1.359(14) . ?
N2A N3A 1.347(10) . ?
N2A C13A 1.446(15) . ?
C1B C2B 1.336(17) . ?
C1B C6B 1.457(16) . ?
C1B N1B 1.505(15) . ?
C13B C14B 1.494(16) . ?
C6B C5B 1.306(16) . ?
C6B H6B 0.93 . ?
O2B N1B 1.178(13) . ?
C14B H14D 0.96 . ?
C14B H14E 0.96 . ?
C14B H14F 0.96 . ?
C2B H2B 0.93 . ?
C13A O5A 1.230(15) . ?
C13A C14A 1.486(15) . ?
N1B O1B 1.193(13) . ?
C14A H14B 0.96 . ?
C14A H14C 0.96 . ?
C14A H14A 0.96 . ?
O2A N1A 1.250(18) . ?
N1A O1A 1.17(2) . ?
 
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
C1A C2A C3A 123.8(15) . . ?
C1A C2A H2A 118.1 . . ?
C3A C2A H2A 118.1 . . ?
C6A C1A C2A 121.7(13) . . ?
C6A C1A N1A 117.5(15) . . ?
C2A C1A N1A 120.7(15) . . ?
C1A C6A C5A 120.7(13) . . ?
C1A C6A H6A 119.6 . . ?
C5A C6A H6A 119.7 . . ?
C5A C4A N2A 121.0(11) . . ?
C5A C4A C3A 121.0(11) . . ?
N2A C4A C3A 118.0(12) . . ?
C4A C5A C6A 117.2(12) . . ?
C4A C5A Cl2A 115.5(10) . . ?
C6A C5A Cl2A 126.4(12) . . ?
C2A C3A C4A 115.4(15) . . ?
C2A C3A Cl1A 122.9(13) . . ?
C4A C3A Cl1A 121.6(10) . . ?
C8B C9B C10B 119.3(8) . . ?
C8B C9B H9B 120.4 . . ?
C10B C9B H9B 120.4 . . ?
C9B C8B C7B 121.2(7) . . ?
C9B C8B Cl3B 118.3(7) . . ?
C7B C8B Cl3B 120.5(7) . . ?
O3A N5A O4A 121.7(8) . . ?
O3A N5A C10A 119.8(8) . . ?
O4A N5A C10A 118.5(8) . . ?
C11A C12A C7A 121.8(8) . . ?
C11A C12A H15A 119.1 . . ?
C7A C12A H15A 119.1 . . ?
O4B N5B O3B 125.6(9) . . ?
O4B N5B C10B 117.9(9) . . ?
O3B N5B C10B 116.5(8) . . ?
C7A C8A C9A 122.3(8) . . ?
C7A C8A Cl3A 118.8(7) . . ?
C9A C8A Cl3A 118.7(7) . . ?
C10A C9A C8A 116.5(8) . . ?
C10A C9A H9A 121.7 . . ?
C8A C9A H9A 121.7 . . ?
N3B N4B C7B 111.9(7) . . ?
C11B C12B C7B 119.9(8) . . ?
C11B C12B H12B 120 . . ?
C7B C12B H12B 120 . . ?
C9A C10A C11A 122.6(8) . . ?
C9A C10A N5A 117.6(8) . . ?
C11A C10A N5A 119.8(7) . . ?
C10B C11B C12B 119.1(8) . . ?
C10B C11B H11B 120.5 . . ?
C12B C11B H11B 120.5 . . ?
C12A C7A C8A 118.5(8) . . ?
C12A C7A N4A 123.3(8) . . ?
C8A C7A N4A 117.9(7) . . ?
C11B C10B C9B 121.9(8) . . ?
C11B C10B N5B 118.7(7) . . ?
C9B C10B N5B 119.4(8) . . ?
C8B C7B C12B 118.6(8) . . ?
C8B C7B N4B 119.9(7) . . ?
C12B C7B N4B 121.5(8) . . ?
N3A N4A C7A 110.9(7) . . ?
C12A C11A C10A 118.1(7) . . ?
C12A C11A H11A 121 . . ?
C10A C11A H11A 121 . . ?
N4B N3B N2B 113.1(8) . . ?
C5B C4B C3B 120.5(9) . . ?
C5B C4B N2B 119.7(9) . . ?
C3B C4B N2B 119.8(9) . . ?
C2B C3B C4B 120.8(10) . . ?
C2B C3B Cl1B 117.5(9) . . ?
C4B C3B Cl1B 121.1(9) . . ?
C13B N2B N3B 118.0(9) . . ?
C13B N2B C4B 122.1(9) . . ?
N3B N2B C4B 119.8(8) . . ?
N3A N2A C4A 124.0(8) . . ?
N3A N2A C13A 116.7(9) . . ?
C4A N2A C13A 119.3(9) . . ?
C2B C1B C6B 122.5(11) . . ?
C2B C1B N1B 118.4(12) . . ?
C6B C1B N1B 119.0(11) . . ?
N4A N3A N2A 113.7(8) . . ?
O5B C13B N2B 119.0(12) . . ?
O5B C13B C14B 123.9(11) . . ?
N2B C13B C14B 117.0(10) . . ?
C5B C6B C1B 118.0(12) . . ?
C5B C6B H6B 121 . . ?
C1B C6B H6B 121 . . ?
C6B C5B C4B 121.0(11) . . ?
C6B C5B Cl2B 120.5(10) . . ?
C4B C5B Cl2B 118.5(9) . . ?
C13B C14B H14D 109.5 . . ?
C13B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C13B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C1B C2B C3B 117.0(10) . . ?
C1B C2B H2B 121.5 . . ?
C3B C2B H2B 121.5 . . ?
O5A C13A N2A 116.1(11) . . ?
O5A C13A C14A 126.2(13) . . ?
N2A C13A C14A 117.7(12) . . ?
O2B N1B O1B 125.7(12) . . ?
O2B N1B C1B 116.5(12) . . ?
O1B N1B C1B 117.7(12) . . ?
C13A C14A H14B 109.5 . . ?
C13A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C13A C14A H14A 109.5 . . ?
H14B C14A H14A 109.5 . . ?
H14C C14A H14A 109.5 . . ?
O1A N1A O2A 133(2) . . ?
O1A N1A C1A 112.6(17) . . ?
O2A N1A C1A 114.1(17) . . ?