# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Prof. Ognjen Miljanic'
_publ_contact_author_email       miljanic@uh.edu

_publ_section_title              
;
Crystal structures of 8-arylethynyl
substituted guanosine derivatives:
are hydrogen-bonded ribbons a surprise?
;
loop_
_publ_author_name
J.Lim
O.Miljanic

data_k1220
_database_code_depnum_ccdc_archive 'CCDC 806420'
#TrackingRef '- Compounds 3 and 4.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 N6 O8, 2 C H Cl3'
_chemical_formula_sum            'C27 H24 Cl6 N6 O8'
_chemical_formula_weight         773.22
_chemical_absolute_configuration ad

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.7267(6)
_cell_length_b                   10.5251(7)
_cell_length_c                   34.007(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3481.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4080
_cell_measurement_theta_min      1.20
_cell_measurement_theta_max      23.54

_exptl_crystal_description       'thin plate'
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1576
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.7599
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_process_details   ?

_publ_section_experimental       
;
All measurements were made with a Siemens SMART platform
diffractometer equipped with a 4K CCD APEX II detector. A
hemisphere of data (1271 frames at 6 cm detector distance)
was collected using a narrow-frame algorithm with scan widths
of 0.30\% in omega and an exposure time of 40 s/frame. The
data were integrated using the Bruker-Nonius SAINT program,
with the intensities corrected for Lorentz factor, polarization,
air absorption, and absorption due to variation in the path
length through the detector faceplate. A psi scan absorption
correction was applied based on the entire data set. Redundant
reflections were averaged. Final cell constants were refined
using 4080 reflections having I>10\s(I), and these, along with
other information pertinent to data collection and refinement,
are listed in Table 1. The Laue symmetry was determined to
be mmm, and from the systematic absences noted the space group
was shown unambiguously to be P2(1)2(1)2(1). The asymmetric unit
consists one heterocyclic molecule and two molecules of chloroform
solvent. The main molecule has disorder in the phenylcyanide group,
and both of the solvent molecules are also disordered. Ideal rigid
body groups were used to model each of the disordered moieties. The
C27 solvent molecule is massively disordered, with at least four
different orientations. Based on a reasonable isotropic displacement
parameter only 75% total occupancy could be found and refined,
however for all calculations it is assumed that the site is fully
occupied.
;

_publ_section_figure_captions    
;
Fig. 1 -- View of the molecule showing the atom numbering
scheme. Thermal ellipsoids are 40% equiprobability envelopes,
with hydrogens omitted.

Fig. 2 -- Isotropic view of the molecule.

Fig. 3 -- View of the hydrogen bonding arrangement. Only the
hydrogens attached to nitrogen are drawn.

Fig. 4 -- Packing of the molecules in the unit cell.
;

_diffrn_ambient_temperature      223(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  'Bruker APEX II CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 4K
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            15676
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         1.20
_diffrn_reflns_theta_max         23.54
_reflns_number_total             5190
_reflns_number_gt                3072
_reflns_threshold_expression     >4sigma(I)

_computing_data_collection       'APEX2 v1.0-27 (Bruker-Nonius, 2005)'
_computing_cell_refinement       'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_data_reduction        'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_structure_solution    'SHELXS v6.12 (G.M. Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL v6.12 (G.M. Sheldrick, 2001)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^ > 4sigma(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^)+(0.1176P)^2^+3.2496P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(14)
_refine_ls_number_reflns         5162
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.2060
_refine_ls_wR_factor_gt          0.1687
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
O1 O 0.4549(4) 0.4962(4) 0.67173(12) 0.0425(10) Uani 1 1 d . . .
O2 O 0.4095(4) 0.5398(4) 0.57958(11) 0.0412(10) Uani 1 1 d . . .
O3 O 0.3695(6) 0.7116(5) 0.54212(14) 0.0679(15) Uani 1 1 d . . .
O4 O 0.6061(4) 0.7068(4) 0.60191(11) 0.0425(10) Uani 1 1 d . . .
O5 O 0.5230(6) 0.9053(5) 0.60695(16) 0.0698(15) Uani 1 1 d . . .
O6 O 0.6228(4) 0.6702(4) 0.71475(12) 0.0473(11) Uani 1 1 d . . .
O7 O 0.7234(6) 0.8352(5) 0.68485(15) 0.0713(15) Uani 1 1 d . . .
O8 O -0.0937(4) 0.6752(4) 0.75801(11) 0.0414(10) Uani 1 1 d . . .
N1 N 0.2191(5) 0.5304(4) 0.66755(13) 0.0354(11) Uani 1 1 d . . .
N2 N 0.2508(5) 0.7484(4) 0.68961(14) 0.0348(11) Uani 1 1 d . . .
N3 N 0.0780(5) 0.8062(4) 0.73636(13) 0.0350(11) Uani 1 1 d . . .
H3N H 0.0483 0.8661 0.7518 0.042 Uiso 1 1 calc R . .
N4 N 0.0300(5) 0.4779(4) 0.70261(14) 0.0354(11) Uani 1 1 d . . .
N5 N 0.2442(6) 0.9489(5) 0.71748(17) 0.0426(12) Uani 1 1 d . . .
H5A H 0.318(7) 0.980(6) 0.7003(19) 0.051 Uiso 1 1 d . . .
H5B H 0.199(7) 1.018(6) 0.7315(18) 0.051 Uiso 1 1 d . . .
N6 N 0.0472(16) -0.3721(14) 0.5625(5) 0.077(4) Uiso 0.50 1 d P A 1
N6' N 0.0292(16) -0.3976(14) 0.5852(5) 0.077(4) Uiso 0.50 1 d P A 2
C1 C 0.3409(6) 0.5073(5) 0.64477(16) 0.0350(13) Uani 1 1 d . . .
H1 H 0.3299 0.4254 0.6308 0.042 Uiso 1 1 calc R . .
C2 C 0.3803(6) 0.6094(5) 0.61473(16) 0.0369(14) Uani 1 1 d . . .
H2 H 0.3072 0.6736 0.6110 0.044 Uiso 1 1 calc R . .
C3 C 0.5107(6) 0.6655(5) 0.63159(16) 0.0346(13) Uani 1 1 d . . .
H3 H 0.4887 0.7363 0.6497 0.042 Uiso 1 1 calc R . .
C4 C 0.5737(6) 0.5555(5) 0.65406(17) 0.0391(14) Uani 1 1 d . . .
H4 H 0.6156 0.4955 0.6351 0.047 Uiso 1 1 calc R . .
C5 C 0.4032(8) 0.6036(7) 0.54487(19) 0.0531(17) Uani 1 1 d . . .
C6 C 0.4429(11) 0.5207(9) 0.5115(2) 0.090(3) Uani 1 1 d . . .
H6A H 0.4386 0.5687 0.4872 0.135 Uiso 1 1 calc R . .
H6B H 0.3803 0.4491 0.5100 0.135 Uiso 1 1 calc R . .
H6C H 0.5359 0.4899 0.5155 0.135 Uiso 1 1 calc R . .
C7 C 0.5989(7) 0.8309(7) 0.5914(2) 0.0522(17) Uani 1 1 d . . .
C8 C 0.6954(10) 0.8573(8) 0.5587(2) 0.078(3) Uani 1 1 d . . .
H8A H 0.7468 0.9342 0.5643 0.118 Uiso 1 1 calc R . .
H8B H 0.6441 0.8684 0.5345 0.118 Uiso 1 1 calc R . .
H8C H 0.7587 0.7866 0.5558 0.118 Uiso 1 1 calc R . .
C9 C 0.6753(7) 0.5844(6) 0.68557(18) 0.0443(15) Uani 1 1 d . . .
H9A H 0.7027 0.5050 0.6984 0.053 Uiso 1 1 calc R . .
H9B H 0.7576 0.6218 0.6736 0.053 Uiso 1 1 calc R . .
C10 C 0.6569(8) 0.7929(7) 0.7121(2) 0.0540(18) Uani 1 1 d . . .
C11 C 0.6105(10) 0.8667(8) 0.7464(2) 0.072(2) Uani 1 1 d . . .
H11A H 0.5847 0.9516 0.7380 0.108 Uiso 1 1 calc R . .
H11B H 0.6844 0.8721 0.7654 0.108 Uiso 1 1 calc R . .
H11C H 0.5317 0.8251 0.7582 0.108 Uiso 1 1 calc R . .
C12 C 0.1852(6) 0.6348(5) 0.68970(16) 0.0344(13) Uani 1 1 d . . .
C13 C 0.1912(6) 0.8324(5) 0.71370(16) 0.0354(13) Uani 1 1 d . . .
C14 C 0.0062(6) 0.6905(5) 0.73662(17) 0.0356(14) Uani 1 1 d . . .
C15 C 0.0680(6) 0.6012(5) 0.71063(16) 0.0339(13) Uani 1 1 d . . .
C16 C 0.1215(6) 0.4380(5) 0.67710(16) 0.0349(14) Uani 1 1 d . . .
C17 C 0.1215(6) 0.3147(5) 0.65921(17) 0.0376(13) Uani 1 1 d . . .
C18 C 0.1137(6) 0.2120(6) 0.64547(18) 0.0400(14) Uani 1 1 d . . .
C19 C 0.1037(13) 0.0888(7) 0.6286(3) 0.035(8) Uiso 0.50 1 d PG A 1
C20 C 0.0040(11) 0.0051(8) 0.6422(3) 0.032(4) Uiso 0.50 1 d PG A 1
H20 H -0.0544 0.0292 0.6629 0.039 Uiso 0.50 1 d PG A 1
C21 C -0.0095(8) -0.1143(7) 0.6252(3) 0.030(3) Uiso 0.50 1 d PG A 1
H21 H -0.0769 -0.1709 0.6344 0.036 Uiso 0.50 1 d PG A 1
C22 C 0.0768(7) -0.1499(5) 0.5945(2) 0.029(3) Uiso 0.50 1 d PG A 1
C23 C 0.1765(9) -0.0662(8) 0.5809(3) 0.044(4) Uiso 0.50 1 d PG A 1
H23 H 0.2348 -0.0903 0.5602 0.053 Uiso 0.50 1 d PG A 1
C24 C 0.1899(12) 0.0532(8) 0.5979(4) 0.047(5) Uiso 0.50 1 d PG A 1
H24 H 0.2573 0.1098 0.5887 0.057 Uiso 0.50 1 d PG A 1
C25 C 0.0628(11) -0.2736(7) 0.5768(3) 0.046(3) Uiso 0.50 1 d PG A 1
C19' C 0.0958(13) 0.0847(7) 0.6326(4) 0.036(7) Uiso 0.50 1 d PG A 2
C20' C -0.0043(13) 0.0093(9) 0.6501(4) 0.055(5) Uiso 0.50 1 d PG A 2
H20' H -0.0592 0.0425 0.6704 0.066 Uiso 0.50 1 d PG A 2
C21' C -0.0231(10) -0.1153(8) 0.6376(3) 0.058(4) Uiso 0.50 1 d PG A 2
H21' H -0.0907 -0.1663 0.6495 0.070 Uiso 0.50 1 d PG A 2
C22' C 0.0582(7) -0.1644(6) 0.6077(2) 0.038(3) Uiso 0.50 1 d PG A 2
C23' C 0.1582(10) -0.0889(8) 0.5901(3) 0.042(3) Uiso 0.50 1 d PG A 2
H23' H 0.2131 -0.1221 0.5698 0.050 Uiso 0.50 1 d PG A 2
C24' C 0.1770(12) 0.0356(8) 0.6026(3) 0.040(4) Uiso 0.50 1 d PG A 2
H24' H 0.2446 0.0866 0.5908 0.048 Uiso 0.50 1 d PG A 2
C25' C 0.0387(11) -0.2934(6) 0.5947(4) 0.051(3) Uiso 0.50 1 d PG A 2
C26 C 0.37121(17) 0.63904(14) 0.84231(5) 0.060(2) Uani 0.85 1 d PG B 1
H26 H 0.3546 0.5463 0.8432 0.072 Uiso 0.85 1 d PG B 1
Cl1 Cl 0.2854(2) 0.7006(3) 0.80166(7) 0.0945(10) Uani 0.85 1 d PG B 1
Cl2 Cl 0.54744(16) 0.6644(2) 0.83836(7) 0.0725(7) Uani 0.85 1 d PG B 1
Cl3 Cl 0.3076(3) 0.7059(3) 0.88542(6) 0.1008(10) Uani 0.85 1 d PG B 1
C26' C 0.3908(14) 0.6671(11) 0.8511(4) 0.050 Uiso 0.15 1 d PG C 2
H26' H 0.3645 0.5788 0.8577 0.060 Uiso 0.15 1 d PG C 2
Cl1' Cl 0.2443(14) 0.7478(18) 0.8357(5) 0.109(3) Uiso 0.15 1 d PG C 2
Cl2' Cl 0.5132(17) 0.662(2) 0.8139(5) 0.109(3) Uiso 0.15 1 d PG C 2
Cl3' Cl 0.4582(18) 0.7377(18) 0.8932(4) 0.109(3) Uiso 0.15 1 d PG C 2
C27 C 0.4318(7) 0.1036(6) 0.4735(2) 0.045(3) Uiso 0.26 1 d PG D 1
H27 H 0.4949 0.0370 0.4638 0.054 Uiso 0.26 1 d PG D 1
Cl4 Cl 0.2640(8) 0.0569(8) 0.4633(2) 0.0912(17) Uiso 0.26 1 d PG D 1
Cl5 Cl 0.4710(10) 0.2453(8) 0.4497(2) 0.0912(17) Uiso 0.26 1 d PG D 1
Cl6 Cl 0.4555(11) 0.1187(10) 0.5240(2) 0.0912(17) Uiso 0.26 1 d PG D 1
C27' C 0.4382(6) 0.1281(5) 0.48316(17) 0.045(3) Uiso 0.29 1 d PG E 2
H27' H 0.4426 0.0386 0.4743 0.054 Uiso 0.29 1 d PG E 2
Cl4' Cl 0.2676(6) 0.1774(9) 0.4815(2) 0.0917(15) Uiso 0.29 1 d PG E 2
Cl5' Cl 0.5393(8) 0.2195(8) 0.4518(2) 0.0917(15) Uiso 0.29 1 d PG E 2
Cl6' Cl 0.5002(8) 0.1356(9) 0.53110(19) 0.0917(15) Uiso 0.29 1 d PG E 2
C27X C 0.4396(19) 0.0944(15) 0.4629(4) 0.045(3) Uiso 0.11 1 d PG F 3
H27X H 0.4421 0.0500 0.4372 0.054 Uiso 0.11 1 d PG F 3
Cl4X Cl 0.5957(18) 0.172(2) 0.4695(8) 0.103(4) Uiso 0.11 1 d PG F 3
Cl5X Cl 0.414(2) -0.0183(17) 0.4996(7) 0.103(4) Uiso 0.11 1 d PG F 3
Cl6X Cl 0.305(2) 0.203(2) 0.4620(8) 0.103(4) Uiso 0.11 1 d PG F 3
C27Y C 0.463(2) 0.1328(17) 0.4736(5) 0.045(3) Uiso 0.09 1 d PG G 4
H27Y H 0.4724 0.0529 0.4585 0.054 Uiso 0.09 1 d PG G 4
Cl4Y Cl 0.373(3) 0.242(3) 0.4450(6) 0.089(5) Uiso 0.09 1 d PG G 4
Cl5Y Cl 0.374(3) 0.100(3) 0.5168(7) 0.089(5) Uiso 0.09 1 d PG G 4
Cl6Y Cl 0.6271(19) 0.190(3) 0.4840(7) 0.089(5) Uiso 0.09 1 d PG G 4

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
O1 0.039(2) 0.043(2) 0.045(2) 0.0086(19) 0.0028(19) 0.0002(19)
O2 0.049(3) 0.040(2) 0.035(2) -0.0056(18) -0.002(2) 0.0076(19)
O3 0.085(4) 0.069(3) 0.049(3) 0.008(2) 0.002(3) 0.029(3)
O4 0.041(2) 0.043(2) 0.044(2) 0.0051(19) 0.0108(19) 0.0012(19)
O5 0.097(4) 0.038(3) 0.075(3) 0.002(2) 0.014(3) -0.007(3)
O6 0.045(3) 0.050(3) 0.047(3) 0.003(2) 0.004(2) -0.006(2)
O7 0.091(4) 0.062(3) 0.061(3) 0.000(3) 0.013(3) -0.017(3)
O8 0.042(2) 0.034(2) 0.048(2) -0.0032(18) 0.016(2) -0.004(2)
N1 0.040(3) 0.031(2) 0.035(3) 0.001(2) 0.004(2) 0.001(2)
N2 0.036(3) 0.027(2) 0.041(3) -0.004(2) 0.005(2) 0.001(2)
N3 0.034(3) 0.026(2) 0.045(3) -0.004(2) 0.006(2) -0.002(2)
N4 0.033(3) 0.030(3) 0.043(3) -0.007(2) 0.003(2) 0.001(2)
N5 0.041(3) 0.030(3) 0.057(3) -0.006(2) 0.004(3) -0.004(2)
C1 0.036(3) 0.028(3) 0.041(3) -0.006(2) 0.000(3) 0.004(3)
C2 0.042(4) 0.035(3) 0.033(3) -0.003(3) 0.006(3) 0.004(3)
C3 0.040(3) 0.035(3) 0.029(3) 0.007(2) 0.007(2) 0.002(3)
C4 0.042(4) 0.035(3) 0.039(3) 0.003(3) 0.010(3) 0.000(3)
C5 0.055(4) 0.060(4) 0.044(4) -0.001(3) -0.008(3) 0.020(4)
C6 0.127(8) 0.106(7) 0.038(4) -0.016(4) 0.001(5) 0.055(6)
C7 0.051(4) 0.047(4) 0.059(4) 0.009(4) 0.002(3) -0.011(4)
C8 0.076(6) 0.077(6) 0.082(6) 0.034(4) 0.010(5) -0.010(5)
C9 0.038(4) 0.048(4) 0.047(4) 0.005(3) -0.007(3) 0.002(3)
C10 0.057(5) 0.069(5) 0.036(4) -0.008(4) -0.012(3) 0.000(4)
C11 0.078(6) 0.075(5) 0.062(5) -0.015(4) 0.001(4) -0.006(4)
C12 0.035(3) 0.032(3) 0.037(3) -0.002(2) 0.004(3) 0.003(3)
C13 0.038(3) 0.029(3) 0.040(3) 0.002(3) -0.003(3) -0.006(3)
C14 0.040(4) 0.027(3) 0.040(3) 0.001(3) -0.008(3) 0.002(3)
C15 0.037(4) 0.026(3) 0.039(3) -0.002(2) 0.000(3) -0.001(3)
C16 0.041(4) 0.028(3) 0.035(3) 0.001(3) 0.000(3) -0.001(3)
C17 0.034(3) 0.038(3) 0.040(3) -0.002(3) 0.000(3) -0.003(3)
C18 0.037(4) 0.040(4) 0.043(3) -0.012(3) 0.002(3) 0.002(3)
C26 0.054(5) 0.041(4) 0.084(6) 0.009(4) -0.025(5) -0.006(4)
Cl1 0.088(2) 0.0892(18) 0.107(2) 0.0467(17) -0.0437(16) -0.0228(15)
Cl2 0.0560(14) 0.0601(13) 0.1015(19) 0.0091(13) -0.0130(13) 0.0014(11)
Cl3 0.119(3) 0.0812(18) 0.102(2) -0.0076(16) 0.0260(18) 0.0171(17)

_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
O1 C4 1.444(7) . ?
O1 C1 1.444(7) . ?
O2 C5 1.360(8) . ?
O2 C2 1.430(6) . ?
O3 C5 1.186(8) . ?
O4 C7 1.357(8) . ?
O4 C3 1.438(7) . ?
O5 C7 1.198(8) . ?
O6 C10 1.337(9) . ?
O6 C9 1.435(7) . ?
O7 C10 1.214(8) . ?
O8 C14 1.225(7) . ?
N1 C12 1.373(7) . ?
N1 C16 1.397(7) . ?
N1 C1 1.437(7) . ?
N2 C13 1.338(7) . ?
N2 C12 1.356(7) . ?
N3 C13 1.373(7) . ?
N3 C14 1.403(7) . ?
N4 C16 1.312(7) . ?
N4 C15 1.376(7) . ?
N5 C13 1.336(7) . ?
N6 C25 1.156(15) . ?
N6' C25' 1.148(15) . ?
C1 C2 1.532(8) . ?
C2 C3 1.512(8) . ?
C3 C4 1.517(8) . ?
C4 C9 1.490(8) . ?
C5 C6 1.483(10) . ?
C7 C8 1.482(10) . ?
C10 C11 1.473(10) . ?
C12 C15 1.390(8) . ?
C14 C15 1.423(8) . ?
C16 C17 1.434(8) . ?
C17 C18 1.180(8) . ?
C18 C19' 1.420(8) . ?
C18 C19 1.420(8) . ?
C19 C20 1.3898 . ?
C19 C24 1.3902 . ?
C20 C21 1.3899 . ?
C21 C22 1.3900 . ?
C22 C23 1.3899 . ?
C22 C25 1.4402 . ?
C23 C24 1.3901 . ?
C19' C24' 1.3899 . ?
C19' C20' 1.3902 . ?
C20' C21' 1.3901 . ?
C21' C22' 1.3898 . ?
C22' C23' 1.3900 . ?
C22' C25' 1.4400 . ?
C23' C24' 1.3899 . ?
C26 Cl2 1.7400 . ?
C26 Cl1 1.7400 . ?
C26 Cl3 1.7400 . ?
C26' Cl3' 1.7398 . ?
C26' Cl1' 1.7399 . ?
C26' Cl2' 1.7402 . ?
C27 Cl6 1.7397 . ?
C27 Cl5 1.7400 . ?
C27 Cl4 1.7401 . ?
C27' Cl5' 1.7398 . ?
C27' Cl4' 1.7398 . ?
C27' Cl6' 1.7400 . ?
C27X Cl6X 1.7400 . ?
C27X Cl4X 1.7400 . ?
C27X Cl5X 1.7401 . ?
C27Y Cl4Y 1.7398 . ?
C27Y Cl5Y 1.7401 . ?
C27Y Cl6Y 1.7401 . ?

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
C4 O1 C1 108.4(4) . . ?
C5 O2 C2 117.6(5) . . ?
C7 O4 C3 116.3(5) . . ?
C10 O6 C9 118.1(5) . . ?
C12 N1 C16 105.5(4) . . ?
C12 N1 C1 129.0(5) . . ?
C16 N1 C1 124.6(4) . . ?
C13 N2 C12 112.2(5) . . ?
C13 N3 C14 125.2(5) . . ?
C16 N4 C15 104.5(5) . . ?
N1 C1 O1 107.8(4) . . ?
N1 C1 C2 116.6(5) . . ?
O1 C1 C2 106.7(5) . . ?
O2 C2 C3 110.5(5) . . ?
O2 C2 C1 104.3(4) . . ?
C3 C2 C1 103.4(5) . . ?
O4 C3 C2 113.1(4) . . ?
O4 C3 C4 108.9(5) . . ?
C2 C3 C4 103.4(5) . . ?
O1 C4 C9 108.7(5) . . ?
O1 C4 C3 102.5(5) . . ?
C9 C4 C3 118.3(5) . . ?
O3 C5 O2 123.7(6) . . ?
O3 C5 C6 125.2(7) . . ?
O2 C5 C6 111.2(6) . . ?
O5 C7 O4 123.0(6) . . ?
O5 C7 C8 126.8(6) . . ?
O4 C7 C8 110.2(7) . . ?
O6 C9 C4 112.9(5) . . ?
O7 C10 O6 122.7(6) . . ?
O7 C10 C11 125.0(7) . . ?
O6 C10 C11 112.3(7) . . ?
N2 C12 N1 126.3(5) . . ?
N2 C12 C15 127.7(5) . . ?
N1 C12 C15 105.9(5) . . ?
N2 C13 N5 119.9(5) . . ?
N2 C13 N3 124.0(5) . . ?
N5 C13 N3 116.1(5) . . ?
O8 C14 N3 120.8(5) . . ?
O8 C14 C15 128.1(5) . . ?
N3 C14 C15 111.1(5) . . ?
N4 C15 C12 111.0(5) . . ?
N4 C15 C14 129.2(5) . . ?
C12 C15 C14 119.7(5) . . ?
N4 C16 N1 113.1(5) . . ?
N4 C16 C17 124.8(5) . . ?
N1 C16 C17 122.1(5) . . ?
C18 C17 C16 175.9(6) . . ?
C17 C18 C19' 173.8(8) . . ?
C17 C18 C19 179.4(9) . . ?
C20 C19 C24 120.0 . . ?
C20 C19 C18 119.5(7) . . ?
C24 C19 C18 120.5(7) . . ?
C19 C20 C21 120.0 . . ?
C20 C21 C22 120.0 . . ?
C23 C22 C21 120.0 . . ?
C23 C22 C25 120.0 . . ?
C21 C22 C25 120.0 . . ?
C22 C23 C24 120.0 . . ?
C23 C24 C19 120.0 . . ?
N6 C25 C22 177.8(11) . . ?
C24' C19' C20' 120.0 . . ?
C24' C19' C18 120.5(7) . . ?
C20' C19' C18 119.5(7) . . ?
C21' C20' C19' 120.0 . . ?
C22' C21' C20' 120.0 . . ?
C21' C22' C23' 120.0 . . ?
C21' C22' C25' 120.0 . . ?
C23' C22' C25' 120.0 . . ?
C24' C23' C22' 120.0 . . ?
C23' C24' C19' 120.0 . . ?
N6' C25' C22' 176.7(12) . . ?
Cl2 C26 Cl1 110.7 . . ?
Cl2 C26 Cl3 110.7 . . ?
Cl1 C26 Cl3 110.4 . . ?
Cl3' C26' Cl1' 110.4 . . ?
Cl3' C26' Cl2' 110.7 . . ?
Cl1' C26' Cl2' 110.7 . . ?
Cl6 C27 Cl5 110.7 . . ?
Cl6 C27 Cl4 110.4 . . ?
Cl5 C27 Cl4 110.7 . . ?
Cl5' C27' Cl4' 110.8 . . ?
Cl5' C27' Cl6' 110.7 . . ?
Cl4' C27' Cl6' 110.4 . . ?
Cl6X C27X Cl4X 110.4 . . ?
Cl6X C27X Cl5X 110.7 . . ?
Cl4X C27X Cl5X 110.7 . . ?
Cl4Y C27Y Cl5Y 110.7 . . ?
Cl4Y C27Y Cl6Y 110.4 . . ?
Cl5Y C27Y Cl6Y 110.7 . . ?

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
C12 N1 C1 O1 66.8(7) . . . . ?
C16 N1 C1 O1 -100.7(6) . . . . ?
C12 N1 C1 C2 -53.1(8) . . . . ?
C16 N1 C1 C2 139.5(5) . . . . ?
C4 O1 C1 N1 -142.3(4) . . . . ?
C4 O1 C1 C2 -16.4(5) . . . . ?
C5 O2 C2 C3 -90.8(6) . . . . ?
C5 O2 C2 C1 158.7(5) . . . . ?
N1 C1 C2 O2 -132.9(5) . . . . ?
O1 C1 C2 O2 106.7(5) . . . . ?
N1 C1 C2 C3 111.4(5) . . . . ?
O1 C1 C2 C3 -9.0(5) . . . . ?
C7 O4 C3 C2 94.1(6) . . . . ?
C7 O4 C3 C4 -151.5(5) . . . . ?
O2 C2 C3 O4 35.9(6) . . . . ?
C1 C2 C3 O4 147.0(4) . . . . ?
O2 C2 C3 C4 -81.7(5) . . . . ?
C1 C2 C3 C4 29.4(5) . . . . ?
C1 O1 C4 C9 160.9(4) . . . . ?
C1 O1 C4 C3 34.9(5) . . . . ?
O4 C3 C4 O1 -160.1(4) . . . . ?
C2 C3 C4 O1 -39.6(5) . . . . ?
O4 C3 C4 C9 80.4(6) . . . . ?
C2 C3 C4 C9 -159.0(5) . . . . ?
C2 O2 C5 O3 -3.2(10) . . . . ?
C2 O2 C5 C6 177.0(7) . . . . ?
C3 O4 C7 O5 3.7(9) . . . . ?
C3 O4 C7 C8 -175.8(5) . . . . ?
C10 O6 C9 C4 -99.2(6) . . . . ?
O1 C4 C9 O6 -60.8(6) . . . . ?
C3 C4 C9 O6 55.4(7) . . . . ?
C9 O6 C10 O7 4.3(10) . . . . ?
C9 O6 C10 C11 -172.9(6) . . . . ?
C13 N2 C12 N1 178.4(5) . . . . ?
C13 N2 C12 C15 1.2(8) . . . . ?
C16 N1 C12 N2 -179.0(5) . . . . ?
C1 N1 C12 N2 11.7(9) . . . . ?
C16 N1 C12 C15 -1.3(6) . . . . ?
C1 N1 C12 C15 -170.6(5) . . . . ?
C12 N2 C13 N5 179.2(5) . . . . ?
C12 N2 C13 N3 1.0(8) . . . . ?
C14 N3 C13 N2 -2.3(8) . . . . ?
C14 N3 C13 N5 179.5(5) . . . . ?
C13 N3 C14 O8 179.6(5) . . . . ?
C13 N3 C14 C15 1.2(7) . . . . ?
C16 N4 C15 C12 -0.5(6) . . . . ?
C16 N4 C15 C14 -179.4(6) . . . . ?
N2 C12 C15 N4 178.8(5) . . . . ?
N1 C12 C15 N4 1.2(6) . . . . ?
N2 C12 C15 C14 -2.1(9) . . . . ?
N1 C12 C15 C14 -179.8(5) . . . . ?
O8 C14 C15 N4 1.3(10) . . . . ?
N3 C14 C15 N4 179.6(5) . . . . ?
O8 C14 C15 C12 -177.5(6) . . . . ?
N3 C14 C15 C12 0.8(7) . . . . ?
C15 N4 C16 N1 -0.3(6) . . . . ?
C15 N4 C16 C17 -178.2(5) . . . . ?
C12 N1 C16 N4 1.0(6) . . . . ?
C1 N1 C16 N4 171.0(5) . . . . ?
C12 N1 C16 C17 179.0(5) . . . . ?
C1 N1 C16 C17 -11.1(8) . . . . ?
C19' C18 C19 C20 21(9) . . . . ?
C19' C18 C19 C24 -161(10) . . . . ?
C24 C19 C20 C21 0.0 . . . . ?
C18 C19 C20 C21 178.2(10) . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C20 C21 C22 C25 -180.0 . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C25 C22 C23 C24 180.0 . . . . ?
C22 C23 C24 C19 0.0 . . . . ?
C20 C19 C24 C23 0.0 . . . . ?
C18 C19 C24 C23 -178.1(10) . . . . ?
C19 C18 C19' C24' 19(9) . . . . ?
C19 C18 C19' C20' -160(10) . . . . ?
C24' C19' C20' C21' 0.0 . . . . ?
C18 C19' C20' C21' 179.8(10) . . . . ?
C19' C20' C21' C22' 0.0 . . . . ?
C20' C21' C22' C23' 0.0 . . . . ?
C20' C21' C22' C25' 180.0 . . . . ?
C21' C22' C23' C24' 0.0 . . . . ?
C25' C22' C23' C24' -180.0 . . . . ?
C22' C23' C24' C19' 0.0 . . . . ?
C20' C19' C24' C23' 0.0 . . . . ?
C18 C19' C24' C23' -179.7(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3N N4 0.87 2.09 2.945(6) 167.7 3_556
N5 H5A Cl2 0.98(7) 2.68(7) 3.586(12) 153(5) 3_656
N5 H5A Cl2' 0.98(7) 2.57(11) 3.43(8) 146(5) 3_656
N5 H5B O8 0.97(7) 1.98(7) 2.917(7) 161(5) 3_556

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        23.54
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.082
#===END

data_k1230
_database_code_depnum_ccdc_archive 'CCDC 806421'
#TrackingRef '- Compounds 3 and 4.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H22 N6 O8, 2 C H Cl3'
_chemical_formula_sum            'C25 H24 Cl6 N6 O8'
_chemical_formula_weight         749.20
_chemical_absolute_configuration ad

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.754(1)
_cell_length_b                   10.353(1)
_cell_length_c                   31.859(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3217.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2884
_cell_measurement_theta_min      1.28
_cell_measurement_theta_max      23.64

_exptl_crystal_description       'flat column'
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1528
_exptl_absorpt_coefficient_mu    0.590
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.7244
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_process_details   'SHELXS v6.12'

_publ_section_experimental       
;
All measurements were made with a Siemens SMART platform
diffractometer equipped with a 4K CCD APEX II detector. A
hemisphere of data (1271 frames at 6 cm detector distance)
was collected using a narrow-frame algorithm with scan widths
of 0.30\% in omega and an exposure time of 40 s/frame. The
data were integrated using the Bruker-Nonius SAINT program,
with the intensities corrected for Lorentz factor, polarization,
air absorption, and absorption due to variation in the path
length through the detector faceplate. A psi scan absorption
correction was applied based on the entire data set. Redundant
reflections were averaged. Final cell constants were refined
using 2884 reflections having I>10\s(I), and these, along with
other information pertinent to data collection and refinement,
are listed in Table 1. The Laue symmetry was determined to
be mmm, and from the systematic absences noted the space group
was shown unambiguously to be P2(1)2(1)2(1). The asymmetric
unit consists of one organic molecule and two molecules of
disordered chloroform solvent. The disorder was treated by
refinement of ideal rigid body models, with population factors
estimated by comparison of the isotropic displacement parameters
involved.
;

_publ_section_figure_captions    
;
Fig. 1 -- View of the molecule showing the atom numbering
scheme. Thermal ellipsoids are 50% equiprobability envelopes,
with hydrogens omitted.

Fig. 2 -- Isotropic view of the molecule.

Fig. 3 -- View of the hydrogen bonding arrangement. Only the
hydrogens attached to nitrogen are shown.

Fig. 4 -- Packing of the molecules in the unit cell.
;

_diffrn_ambient_temperature      223(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  'Bruker APEX II CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 4K
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            13581
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_sigmaI/netI    0.0706
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.28
_diffrn_reflns_theta_max         23.64
_reflns_number_total             4782
_reflns_number_gt                2814
_reflns_threshold_expression     >4sigma(I)

_computing_data_collection       'APEX2 v1.0-27 (Bruker-Nonius, 2005)'
_computing_cell_refinement       'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_data_reduction        'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_structure_solution    'SHELXS v6.12 (G.M. Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL v6.12 (G.M. Sheldrick, 2001)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^ > 4sigma(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^)+(0.0343P)^2^+10.0201P] 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    noref
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(15)
_refine_ls_number_reflns         4782
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1686
_refine_ls_wR_factor_gt          0.1242
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_restrained_S_all      1.218
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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
O1 O 0.4570(5) 0.4206(5) 0.66694(14) 0.0251(12) Uani 1 1 d . . .
O2 O 0.4238(5) 0.4547(5) 0.56850(14) 0.0244(11) Uani 1 1 d . . .
O3 O 0.3852(6) 0.6261(6) 0.52708(16) 0.0458(15) Uani 1 1 d . . .
O4 O 0.6014(5) 0.6396(4) 0.59312(14) 0.0266(12) Uani 1 1 d . . .
O5 O 0.5126(6) 0.8376(5) 0.59907(19) 0.0455(16) Uani 1 1 d . . .
O6 O 0.6209(5) 0.6102(5) 0.71164(15) 0.0335(13) Uani 1 1 d . . .
O7 O 0.7263(6) 0.7721(6) 0.67799(19) 0.0493(17) Uani 1 1 d . . .
O8 O -0.0944(5) 0.5962(5) 0.75659(15) 0.0306(12) Uani 1 1 d . . .
N1 N 0.2209(5) 0.4481(5) 0.66160(17) 0.0188(13) Uani 1 1 d . . .
N2 N 0.2506(6) 0.6707(5) 0.68466(18) 0.0235(14) Uani 1 1 d . . .
N3 N 0.0772(6) 0.7287(6) 0.73388(18) 0.0234(14) Uani 1 1 d . . .
H3N H 0.0467 0.7897 0.7502 0.028 Uiso 1 1 calc R . .
N4 N 0.0333(5) 0.3947(5) 0.69887(17) 0.0222(14) Uani 1 1 d . . .
N5 N 0.2457(6) 0.8733(6) 0.71438(19) 0.0292(15) Uani 1 1 d . . .
H5A H 0.3196 0.8939 0.7007 0.035 Uiso 1 1 calc R . .
H5B H 0.2071 0.9293 0.7310 0.035 Uiso 1 1 calc R . .
N6 N 0.0808(7) -0.2520(6) 0.5868(2) 0.0385(17) Uani 1 1 d . . .
C1 C 0.3463(7) 0.4251(7) 0.6380(2) 0.0231(17) Uani 1 1 d . . .
H1 H 0.3390 0.3402 0.6238 0.028 Uiso 1 1 calc R . .
C2 C 0.3818(7) 0.5289(7) 0.6047(2) 0.0211(16) Uani 1 1 d . . .
H2 H 0.3056 0.5894 0.5988 0.025 Uiso 1 1 calc R . .
C3 C 0.5079(6) 0.5940(7) 0.62406(19) 0.0178(15) Uani 1 1 d . . .
H3 H 0.4804 0.6646 0.6433 0.021 Uiso 1 1 calc R . .
C4 C 0.5731(7) 0.4826(7) 0.6484(2) 0.0237(17) Uani 1 1 d . . .
H4 H 0.6169 0.4225 0.6283 0.028 Uiso 1 1 calc R . .
C5 C 0.4197(8) 0.5167(9) 0.5315(2) 0.0319(19) Uani 1 1 d . . .
C6 C 0.4684(10) 0.4290(9) 0.4969(3) 0.052(3) Uani 1 1 d . . .
H6A H 0.4920 0.4802 0.4725 0.078 Uiso 1 1 calc R . .
H6B H 0.3961 0.3686 0.4897 0.078 Uiso 1 1 calc R . .
H6C H 0.5485 0.3816 0.5063 0.078 Uiso 1 1 calc R . .
C7 C 0.5912(8) 0.7659(8) 0.5820(2) 0.0325(19) Uani 1 1 d . . .
C8 C 0.6861(10) 0.7986(9) 0.5471(3) 0.051(3) Uani 1 1 d . . .
H8A H 0.7119 0.8889 0.5490 0.077 Uiso 1 1 calc R . .
H8B H 0.6408 0.7831 0.5204 0.077 Uiso 1 1 calc R . .
H8C H 0.7676 0.7452 0.5490 0.077 Uiso 1 1 calc R . .
C9 C 0.6753(7) 0.5184(8) 0.6818(2) 0.0287(18) Uani 1 1 d . . .
H9A H 0.7035 0.4401 0.6968 0.034 Uiso 1 1 calc R . .
H9B H 0.7569 0.5553 0.6684 0.034 Uiso 1 1 calc R . .
C10 C 0.6608(8) 0.7339(9) 0.7076(3) 0.036(2) Uani 1 1 d . . .
C11 C 0.6148(10) 0.8133(8) 0.7433(3) 0.050(2) Uani 1 1 d . . .
H11A H 0.6305 0.9038 0.7371 0.075 Uiso 1 1 calc R . .
H11B H 0.6657 0.7894 0.7683 0.075 Uiso 1 1 calc R . .
H11C H 0.5177 0.7991 0.7481 0.075 Uiso 1 1 calc R . .
C12 C 0.1864(7) 0.5561(6) 0.6848(2) 0.0199(16) Uani 1 1 d . . .
C13 C 0.1912(7) 0.7552(7) 0.7100(2) 0.0214(16) Uani 1 1 d . . .
C14 C 0.0075(7) 0.6125(7) 0.7340(2) 0.0199(16) Uani 1 1 d . . .
C15 C 0.0694(7) 0.5206(7) 0.7067(2) 0.0213(16) Uani 1 1 d . . .
C16 C 0.1251(7) 0.3529(7) 0.6720(2) 0.0212(15) Uani 1 1 d . . .
C17 C 0.1265(7) 0.2273(7) 0.6535(2) 0.0250(17) Uani 1 1 d . . .
C18 C 0.1174(8) 0.1205(7) 0.6394(2) 0.0262(17) Uani 1 1 d . . .
C19 C 0.1064(7) -0.0045(7) 0.6218(2) 0.0247(17) Uani 1 1 d . . .
C20 C 0.0016(7) -0.0887(7) 0.6343(2) 0.0298(19) Uani 1 1 d . . .
H20 H -0.0626 -0.0638 0.6547 0.036 Uiso 1 1 calc R . .
C21 C -0.0050(9) -0.2087(8) 0.6158(3) 0.041(2) Uani 1 1 d . . .
H21 H -0.0759 -0.2642 0.6244 0.050 Uiso 1 1 calc R . .
C22 C 0.1806(8) -0.1731(8) 0.5752(3) 0.035(2) Uani 1 1 d . . .
H22 H 0.2430 -0.2018 0.5548 0.042 Uiso 1 1 calc R . .
C23 C 0.1977(8) -0.0489(8) 0.5920(2) 0.033(2) Uani 1 1 d . . .
H23 H 0.2705 0.0037 0.5830 0.040 Uiso 1 1 calc R . .
C24 C 0.4860(3) 1.0210(4) 0.45358(11) 0.047(2) Uiso 0.70 1 d PG A 1
H24 H 0.5221 0.9331 0.4484 0.056 Uiso 0.70 1 d PG A 1
Cl1 Cl 0.4023(4) 1.0732(5) 0.40844(10) 0.0857(15) Uani 0.70 1 d PG A 1
Cl2 Cl 0.6234(3) 1.1218(6) 0.46541(16) 0.0756(17) Uani 0.70 1 d PG A 1
Cl3 Cl 0.3720(5) 1.0134(6) 0.49550(10) 0.103(2) Uani 0.70 1 d PG A 1
C25 C 0.6369(9) 1.0733(11) 0.6487(3) 0.048(3) Uiso 0.50 1 d PG B 1
H25 H 0.6546 0.9792 0.6479 0.058 Uiso 0.50 1 d PG B 1
Cl4 Cl 0.4635(9) 1.097(2) 0.6587(3) 0.052(2) Uani 0.50 1 d PG B 1
Cl5 Cl 0.6821(7) 1.1381(9) 0.6002(2) 0.075(2) Uani 0.50 1 d PG B 1
Cl6 Cl 0.7358(13) 1.140(2) 0.6885(3) 0.082(5) Uani 0.50 1 d PG B 1
C24' C 0.4819(11) 1.0377(12) 0.4547(4) 0.047(2) Uiso 0.30 1 d PG C 2
H24' H 0.5110 0.9536 0.4430 0.056 Uiso 0.30 1 d PG C 2
Cl1' Cl 0.4361(15) 1.0147(19) 0.5069(4) 0.122 Uiso 0.30 1 d PG C 2
Cl2' Cl 0.3428(12) 1.0934(17) 0.4256(4) 0.126 Uiso 0.30 1 d PG C 2
Cl3' Cl 0.6190(13) 1.145(2) 0.4511(5) 0.095(6) Uiso 0.30 1 d PG C 2
C25' C 0.6246(9) 1.0840(12) 0.6433(3) 0.048(3) Uiso 0.50 1 d PG D 2
H25' H 0.6509 0.9925 0.6394 0.058 Uiso 0.50 1 d PG D 2
Cl4' Cl 0.4712(11) 1.089(2) 0.6711(4) 0.087(5) Uani 0.50 1 d PG D 2
Cl5' Cl 0.6054(8) 1.1545(9) 0.5941(3) 0.0837(18) Uani 0.50 1 d PG D 2
Cl6' Cl 0.7540(13) 1.161(2) 0.6716(3) 0.079(3) Uani 0.50 1 d PG D 2

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
O1 0.017(3) 0.034(3) 0.024(3) 0.005(2) 0.001(2) -0.003(2)
O2 0.025(3) 0.030(3) 0.018(3) -0.006(2) 0.001(2) -0.001(2)
O3 0.060(4) 0.049(4) 0.029(3) 0.001(3) -0.002(3) 0.015(3)
O4 0.023(3) 0.028(3) 0.029(3) 0.004(2) 0.010(2) -0.002(2)
O5 0.048(4) 0.031(3) 0.058(4) 0.002(3) 0.014(3) 0.003(3)
O6 0.027(3) 0.050(4) 0.023(3) -0.007(3) 0.000(2) 0.000(3)
O7 0.053(4) 0.048(4) 0.047(4) -0.005(3) 0.014(3) -0.016(3)
O8 0.021(3) 0.035(3) 0.035(3) -0.006(3) 0.012(2) 0.001(2)
N1 0.015(3) 0.021(3) 0.020(3) -0.004(3) 0.004(3) -0.002(2)
N2 0.018(3) 0.024(3) 0.028(3) -0.004(3) 0.005(3) -0.004(3)
N3 0.015(3) 0.026(3) 0.030(3) -0.006(3) 0.005(3) 0.000(3)
N4 0.012(3) 0.019(3) 0.036(4) -0.003(3) 0.000(3) -0.002(3)
N5 0.022(3) 0.025(4) 0.040(4) -0.007(3) 0.012(3) -0.002(3)
N6 0.041(4) 0.023(4) 0.051(4) -0.012(3) -0.002(4) 0.002(4)
C1 0.017(4) 0.026(4) 0.026(4) -0.002(3) 0.004(3) 0.002(3)
C2 0.018(4) 0.024(4) 0.022(4) -0.002(3) 0.001(3) 0.002(3)
C3 0.007(3) 0.032(4) 0.014(3) -0.001(3) 0.000(3) -0.006(3)
C4 0.011(4) 0.033(4) 0.027(4) 0.001(3) -0.001(3) 0.001(3)
C5 0.024(5) 0.051(6) 0.021(4) -0.009(4) 0.001(3) -0.001(4)
C6 0.066(7) 0.058(7) 0.033(5) -0.013(5) 0.006(5) 0.006(5)
C7 0.025(5) 0.033(5) 0.040(5) 0.004(4) -0.002(4) -0.009(4)
C8 0.057(6) 0.052(6) 0.044(6) 0.015(5) 0.012(5) -0.011(5)
C9 0.015(4) 0.036(4) 0.035(5) 0.001(4) 0.001(3) 0.001(3)
C10 0.016(4) 0.047(6) 0.044(5) -0.003(5) -0.010(4) -0.002(4)
C11 0.051(6) 0.054(6) 0.045(5) -0.022(5) -0.008(5) 0.000(5)
C12 0.016(4) 0.022(4) 0.022(4) -0.004(3) 0.003(3) 0.003(3)
C13 0.015(4) 0.023(4) 0.027(4) -0.002(4) -0.001(3) 0.003(3)
C14 0.010(4) 0.027(4) 0.022(4) -0.001(3) 0.001(3) -0.001(3)
C15 0.010(4) 0.028(4) 0.026(4) -0.001(3) -0.001(3) 0.000(3)
C16 0.009 0.025(4) 0.029(4) 0.001(3) 0.001(3) -0.001(3)
C17 0.014(4) 0.033(5) 0.028(4) -0.001(4) 0.000(3) -0.001(3)
C18 0.029(4) 0.021(4) 0.029(4) -0.003(4) 0.001(3) 0.000(3)
C19 0.011(4) 0.032(4) 0.031(4) -0.009(3) -0.004(3) 0.003(3)
C20 0.018(4) 0.030(5) 0.042(5) -0.006(4) -0.001(3) -0.002(4)
C21 0.031(5) 0.033(5) 0.060(6) -0.004(5) 0.007(5) -0.007(4)
C22 0.032(5) 0.036(5) 0.037(5) -0.009(4) 0.000(4) 0.010(4)
C23 0.028(5) 0.034(5) 0.037(5) -0.007(4) 0.005(4) 0.001(4)
Cl1 0.057(3) 0.134(4) 0.066(3) 0.032(3) -0.018(2) -0.018(3)
Cl2 0.025(2) 0.078(4) 0.123(5) -0.018(4) -0.009(2) 0.0071(19)
Cl3 0.111(4) 0.134(4) 0.062(3) -0.009(3) 0.042(3) -0.048(4)
Cl4 0.029 0.040(6) 0.087(5) -0.006(5) -0.010(3) 0.001(3)
Cl5 0.089(5) 0.058(4) 0.076(5) 0.003(4) 0.024(5) -0.008(5)
Cl6 0.060(6) 0.077(11) 0.107(7) -0.049(9) -0.037(6) 0.014(5)
Cl4' 0.059(4) 0.045(5) 0.156(12) 0.011(10) 0.049(7) 0.001(6)
Cl5' 0.124 0.047(4) 0.080(4) 0.009(3) -0.016(6) -0.010(6)
Cl6' 0.043(4) 0.056(5) 0.138(9) -0.032(10) -0.033(6) 0.005(4)

_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
O1 C1 1.422(8) . ?
O1 C4 1.430(8) . ?
O2 C5 1.343(9) . ?
O2 C2 1.444(8) . ?
O3 C5 1.190(9) . ?
O4 C7 1.358(9) . ?
O4 C3 1.423(7) . ?
O5 C7 1.198(9) . ?
O6 C10 1.345(10) . ?
O6 C9 1.446(9) . ?
O7 C10 1.207(9) . ?
O8 C14 1.239(8) . ?
N1 C12 1.383(8) . ?
N1 C16 1.398(8) . ?
N1 C1 1.456(8) . ?
N2 C13 1.324(9) . ?
N2 C12 1.342(9) . ?
N3 C14 1.381(9) . ?
N3 C13 1.376(9) . ?
N4 C16 1.313(8) . ?
N4 C15 1.373(9) . ?
N5 C13 1.340(9) . ?
N6 C22 1.323(10) . ?
N6 C21 1.324(10) . ?
C1 C2 1.550(9) . ?
C2 C3 1.532(9) . ?
C3 C4 1.528(9) . ?
C4 C9 1.505(10) . ?
C5 C6 1.505(10) . ?
C7 C8 1.487(11) . ?
C10 C11 1.473(11) . ?
C12 C15 1.386(9) . ?
C14 C15 1.424(9) . ?
C16 C17 1.427(10) . ?
C17 C18 1.197(10) . ?
C18 C19 1.415(10) . ?
C19 C23 1.381(10) . ?
C19 C20 1.401(10) . ?
C20 C21 1.376(11) . ?
C22 C23 1.403(11) . ?
C24 Cl3 1.7399 . ?
C24 Cl2 1.7399 . ?
C24 Cl1 1.7402 . ?
C25 Cl4 1.7399 . ?
C25 Cl6 1.7400 . ?
C25 Cl5 1.7406 . ?
C24' Cl1' 1.7397 . ?
C24' Cl3' 1.7399 . ?
C24' Cl2' 1.7403 . ?
C25' Cl6' 1.7399 . ?
C25' Cl4' 1.7399 . ?
C25' Cl5' 1.7403 . ?

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
C1 O1 C4 108.5(5) . . ?
C5 O2 C2 116.0(6) . . ?
C7 O4 C3 116.9(6) . . ?
C10 O6 C9 117.2(6) . . ?
C12 N1 C16 106.3(5) . . ?
C12 N1 C1 127.8(6) . . ?
C16 N1 C1 124.7(6) . . ?
C13 N2 C12 112.2(6) . . ?
C14 N3 C13 125.0(6) . . ?
C16 N4 C15 104.9(6) . . ?
C22 N6 C21 116.8(7) . . ?
O1 C1 N1 107.9(5) . . ?
O1 C1 C2 107.3(5) . . ?
N1 C1 C2 115.4(6) . . ?
O2 C2 C3 109.2(5) . . ?
O2 C2 C1 104.0(5) . . ?
C3 C2 C1 102.0(5) . . ?
O4 C3 C2 112.4(5) . . ?
O4 C3 C4 109.5(5) . . ?
C2 C3 C4 101.9(6) . . ?
O1 C4 C9 110.0(6) . . ?
O1 C4 C3 102.7(5) . . ?
C9 C4 C3 116.6(6) . . ?
O3 C5 O2 124.5(7) . . ?
O3 C5 C6 125.3(7) . . ?
O2 C5 C6 110.2(7) . . ?
O5 C7 O4 121.7(7) . . ?
O5 C7 C8 126.6(8) . . ?
O4 C7 C8 111.6(7) . . ?
O6 C9 C4 112.6(6) . . ?
O7 C10 O6 122.6(8) . . ?
O7 C10 C11 125.7(8) . . ?
O6 C10 C11 111.7(7) . . ?
N2 C12 N1 126.8(6) . . ?
N2 C12 C15 128.4(6) . . ?
N1 C12 C15 104.8(6) . . ?
N2 C13 N5 119.6(6) . . ?
N2 C13 N3 124.0(7) . . ?
N5 C13 N3 116.4(6) . . ?
O8 C14 N3 121.0(6) . . ?
O8 C14 C15 127.2(7) . . ?
N3 C14 C15 111.8(6) . . ?
N4 C15 C12 111.9(6) . . ?
N4 C15 C14 129.5(6) . . ?
C12 C15 C14 118.6(6) . . ?
N4 C16 N1 112.2(6) . . ?
N4 C16 C17 125.2(6) . . ?
N1 C16 C17 122.6(6) . . ?
C18 C17 C16 174.8(8) . . ?
C17 C18 C19 178.8(8) . . ?
C23 C19 C20 117.3(7) . . ?
C23 C19 C18 121.9(7) . . ?
C20 C19 C18 120.8(7) . . ?
C21 C20 C19 118.3(7) . . ?
N6 C21 C20 125.0(8) . . ?
N6 C22 C23 123.2(8) . . ?
C19 C23 C22 119.3(8) . . ?
Cl3 C24 Cl2 110.7 . . ?
Cl3 C24 Cl1 110.4 . . ?
Cl2 C24 Cl1 110.7 . . ?
Cl4 C25 Cl6 110.4 . . ?
Cl4 C25 Cl5 110.7 . . ?
Cl6 C25 Cl5 110.7 . . ?
Cl1' C24' Cl3' 110.4 . . ?
Cl1' C24' Cl2' 110.7 . . ?
Cl3' C24' Cl2' 110.7 . . ?
Cl6' C25' Cl4' 110.4 . . ?
Cl6' C25' Cl5' 110.7 . . ?
Cl4' C25' Cl5' 110.7 . . ?

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
C4 O1 C1 N1 -141.7(6) . . . . ?
C4 O1 C1 C2 -16.7(7) . . . . ?
C12 N1 C1 O1 64.4(8) . . . . ?
C16 N1 C1 O1 -101.5(7) . . . . ?
C12 N1 C1 C2 -55.6(9) . . . . ?
C16 N1 C1 C2 138.5(6) . . . . ?
C5 O2 C2 C3 -91.6(7) . . . . ?
C5 O2 C2 C1 160.1(6) . . . . ?
O1 C1 C2 O2 103.3(6) . . . . ?
N1 C1 C2 O2 -136.3(6) . . . . ?
O1 C1 C2 C3 -10.2(7) . . . . ?
N1 C1 C2 C3 110.1(6) . . . . ?
C7 O4 C3 C2 96.1(7) . . . . ?
C7 O4 C3 C4 -151.4(6) . . . . ?
O2 C2 C3 O4 38.5(8) . . . . ?
C1 C2 C3 O4 148.1(5) . . . . ?
O2 C2 C3 C4 -78.6(6) . . . . ?
C1 C2 C3 C4 31.0(6) . . . . ?
C1 O1 C4 C9 161.7(6) . . . . ?
C1 O1 C4 C3 36.9(7) . . . . ?
O4 C3 C4 O1 -161.0(5) . . . . ?
C2 C3 C4 O1 -41.9(6) . . . . ?
O4 C3 C4 C9 78.6(7) . . . . ?
C2 C3 C4 C9 -162.2(6) . . . . ?
C2 O2 C5 O3 0.4(11) . . . . ?
C2 O2 C5 C6 178.9(6) . . . . ?
C3 O4 C7 O5 4.2(10) . . . . ?
C3 O4 C7 C8 -175.2(6) . . . . ?
C10 O6 C9 C4 -102.9(7) . . . . ?
O1 C4 C9 O6 -62.6(8) . . . . ?
C3 C4 C9 O6 53.7(8) . . . . ?
C9 O6 C10 O7 8.4(11) . . . . ?
C9 O6 C10 C11 -171.7(6) . . . . ?
C13 N2 C12 N1 179.1(6) . . . . ?
C13 N2 C12 C15 1.7(11) . . . . ?
C16 N1 C12 N2 -179.8(7) . . . . ?
C1 N1 C12 N2 12.2(11) . . . . ?
C16 N1 C12 C15 -1.9(7) . . . . ?
C1 N1 C12 C15 -169.8(6) . . . . ?
C12 N2 C13 N5 177.9(6) . . . . ?
C12 N2 C13 N3 0.3(10) . . . . ?
C14 N3 C13 N2 -1.7(11) . . . . ?
C14 N3 C13 N5 -179.4(6) . . . . ?
C13 N3 C14 O8 179.9(6) . . . . ?
C13 N3 C14 C15 1.1(9) . . . . ?
C16 N4 C15 C12 -1.0(8) . . . . ?
C16 N4 C15 C14 -178.8(7) . . . . ?
N2 C12 C15 N4 179.7(7) . . . . ?
N1 C12 C15 N4 1.9(8) . . . . ?
N2 C12 C15 C14 -2.2(11) . . . . ?
N1 C12 C15 C14 179.9(6) . . . . ?
O8 C14 C15 N4 -0.4(12) . . . . ?
N3 C14 C15 N4 178.3(6) . . . . ?
O8 C14 C15 C12 -178.0(6) . . . . ?
N3 C14 C15 C12 0.7(9) . . . . ?
C15 N4 C16 N1 -0.3(7) . . . . ?
C15 N4 C16 C17 -177.7(7) . . . . ?
C12 N1 C16 N4 1.4(8) . . . . ?
C1 N1 C16 N4 169.8(6) . . . . ?
C12 N1 C16 C17 179.0(6) . . . . ?
C1 N1 C16 C17 -12.6(10) . . . . ?
C23 C19 C20 C21 -0.9(11) . . . . ?
C18 C19 C20 C21 179.4(7) . . . . ?
C22 N6 C21 C20 0.5(12) . . . . ?
C19 C20 C21 N6 0.1(13) . . . . ?
C21 N6 C22 C23 -0.3(12) . . . . ?
C20 C19 C23 C22 1.1(11) . . . . ?
C18 C19 C23 C22 -179.2(7) . . . . ?
N6 C22 C23 C19 -0.5(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3N N4 0.87 2.10 2.951(8) 164.2 3_556
N5 H5A Cl4 0.87 2.86 3.611(14) 145.3 .
N5 H5A Cl4' 0.87 2.67 3.422(16) 145.2 .
N5 H5B O8 0.87 2.09 2.891(8) 153.5 3_556

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        23.64
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.098
#===END