Electronic Supplementary Material for CrystEngComm
This Journal is © The Royal Society of Chemistry 2005

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Prof T N Guru Row'
_publ_contact_author_address     
;
Solid State and Structural Chemistry Unit
Indian Institute of Science
Bangalore
560012
INDIA
;

_publ_contact_author_email       SSCTNG@SSCU.IISC.ERNET.IN
_publ_contact_author_fax         '(91) 80 360 1310 '
_publ_contact_author_phone       '(91) 80 309 2796'

_publ_section_title              
;
Exploring Polymorphism by Solvent Mediation in
Potentially Active Herbicide Metribuzin: A subtle interplay of weak
intermolecular interactions.
;

loop_
_publ_author_name
_publ_author_address

D.Chopra
;
Solid State and Structural Chemistry Unit
Indian Institute of Science
Bangalore 560 012. Karnataka.
India
;
T.P.Mohan
;
India Limited,
Peenya Industrial Area,
Bangalore-560078.
;
K.S.Rao
;
Rallis India Limited,
Peenya Industrial Area,
Bangalore-560078.
;
'T.N.Guru Row'
;
Solid State and Structural Chemistry Unit
Indian Institute of Science
Bangalore 560 012. Karnataka.
India
;

_publ_section_references         
;
Allen, F.H. & Kennard, O. (1993).
Chem. Des. Autom. News., 8, 31-37.

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.

Beurskens, P.T., Admiraal, G., Beurskens, G., Bosman, W.P.,
Garc\'ia-Granda, S., Gould, R.O., Smits, J.M.M. &
Smykalla, C. (1999) The DIRDIF99 program system,
Technical Report of the Crystallography Laboratory,
University of Nijmegen, The Netherlands.

Boer, J.L. de & Duisenberg, A.J.M. (1984). Acta Cryst. A40, C-410.

Boeyens, J.C.A. (1978). J.Cryst.Mol.Struct. 8, 317-320.

Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358.

Enraf-Nonius (1989). CAD-4 Software. Version 5. Enraf-Nonius, Delft,
The Netherlands.

Flack, H.D. (1983). Acta Cryst. A39, 876-881.

LePage, Y. (1987). J. Appl. Cryst. 20, 264-269.

Mackay, A.L. (1984). Acta Cryst. A40, 165-166.

Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018.

Nonius (1998). Collect Software, Nonius, Delft, The Netherlands.

North, A.C.T., Phillips, D.C. & Mathews, F.S. (1968).
Acta Cryst. A24, 351-359.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, 276, 307-326.

Sheldrick, G.M. SHELXL93. Program for crystal structure
refinement. University of G\\"ottingen, Germany, 1993.

Sheldrick, G.M. SHELXL97. Program for crystal structure
refinement. University of G\\"ottingen, Germany, 1997.

Sheldrick, G.M. SHELXS86. Program for Crystal Structure
solution. University of G\\"ottingen, Germany, 1986.

Sheldrick, G.M. SHELXS97. Program for Crystal Structure
solution. University of G\\"ottingen, Germany, 1997.

Spek, A.L. (1987). Acta Cryst. C43, 1233-1235.

Spek, A.L. (1988). J. Appl. Cryst. 21, 578-579.

Spek, A.L. (1990). Acta Cryst. A46, C-34.

Spek, A.L. (1997). HELENA, Program for Datareduction, Utrecht
University, The Netherlands.

Spek, A.L. (1994). Am. Crystallogr. Assoc.-Abstracts, 22, 66.

Wilson, A.J.C. (1992) Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;

data_P2(PLATE)
_database_code_depnum_ccdc_archive 'CCDC 252402'

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H14 N4 O S'
_chemical_formula_structural     ?
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_sum            'C8 H14 N4 O S'
_chemical_formula_weight         214.30
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

_cell_length_a                   6.450(2)
_cell_length_b                   9.401(4)
_cell_length_c                   9.965(4)
_cell_angle_alpha                76.674(5)
_cell_angle_beta                 76.909(5)
_cell_angle_gamma                70.190(5)
_cell_volume                     545.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    660
_cell_measurement_theta_min      1.4
_cell_measurement_theta_max      26.4
_cell_special_details            
; ?
;

_exptl_crystal_description       needles
_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.03
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             228
_exptl_absorpt_coefficient_mu    0.272
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# cylinder 'cylindrical'
# empirical 'empirical from intensities'
# gaussian 'Gaussian from crystal shape'
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# refdelf 'refined from delta-F'
# sphere 'spherical'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.9423
_exptl_absorpt_correction_T_max  0.9919

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;
_diffrn_ambient_temperature      290(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 SMART CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            4014
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.35
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_reduction_process 
;
?
;

_reflns_number_total             1978
_reflns_number_gt                1742
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Farrugia, 1999)'
_computing_publication_material  'PLATON (Spek, 1990)'

#===============================================================================
# 8. REFINEMENT DATA

_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^ > 2sigma(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^)+(0.1563P)^2^+0.2769P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1978
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1735
_refine_ls_wR_factor_gt          0.1639
_refine_ls_goodness_of_fit_ref   0.834
_refine_ls_restrained_S_all      0.834
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.077

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
S1 S -0.08097(11) 0.37753(7) 1.22453(6) 0.0446(3) Uani 1 1 d . . .
N1 N -0.2001(3) 0.3372(3) 1.0003(2) 0.0469(6) Uani 1 1 d . . .
N2 N -0.1506(3) 0.2901(3) 0.8719(2) 0.0471(6) Uani 1 1 d . . .
O1 O 0.4348(3) 0.1221(2) 0.8500(2) 0.0532(5) Uani 1 1 d . . .
N3 N 0.1814(3) 0.2512(2) 1.0116(2) 0.0361(5) Uani 1 1 d . . .
C4 C 0.0914(4) 0.1795(3) 0.6736(3) 0.0429(6) Uani 1 1 d . . .
N4 N 0.3453(4) 0.2339(3) 1.0915(2) 0.0513(6) Uani 1 1 d . . .
H4A H 0.3068 0.2653 1.1707 0.062 Uiso 1 1 calc R . .
H4B H 0.4839 0.1919 1.0612 0.062 Uiso 1 1 calc R . .
C2 C 0.0508(4) 0.2244(3) 0.8173(2) 0.0361(5) Uani 1 1 d . . .
C3 C 0.2417(4) 0.1918(3) 0.8883(2) 0.0370(5) Uani 1 1 d . . .
C1 C -0.0354(4) 0.3183(3) 1.0638(2) 0.0360(5) Uani 1 1 d . . .
C5 C 0.2456(6) 0.2612(4) 0.5707(3) 0.0627(8) Uani 1 1 d . . .
H5A H 0.1822 0.3699 0.5679 0.094 Uiso 1 1 calc R . .
H5B H 0.2628 0.2375 0.4794 0.094 Uiso 1 1 calc R . .
H5C H 0.3888 0.2275 0.6001 0.094 Uiso 1 1 calc R . .
C8 C -0.3812(5) 0.4382(4) 1.2597(3) 0.0604(8) Uani 1 1 d . . .
H8A H -0.4380 0.5218 1.1884 0.091 Uiso 1 1 calc R . .
H8B H -0.4314 0.4710 1.3490 0.091 Uiso 1 1 calc R . .
H8C H -0.4344 0.3542 1.2604 0.091 Uiso 1 1 calc R . .
C7 C -0.1288(5) 0.2295(5) 0.6175(3) 0.0765(11) Uani 1 1 d . . .
H7A H -0.2264 0.1747 0.6768 0.115 Uiso 1 1 calc R . .
H7B H -0.1001 0.2075 0.5244 0.115 Uiso 1 1 calc R . .
H7C H -0.1981 0.3376 0.6159 0.115 Uiso 1 1 calc R . .
C6 C 0.1963(9) 0.0060(4) 0.6829(4) 0.0974(15) Uani 1 1 d . . .
H6A H 0.3397 -0.0243 0.7114 0.146 Uiso 1 1 calc R . .
H6B H 0.2138 -0.0215 0.5931 0.146 Uiso 1 1 calc R . .
H6C H 0.1011 -0.0453 0.7500 0.146 Uiso 1 1 calc R . .

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
S1 0.0537(5) 0.0424(4) 0.0400(4) -0.0125(3) -0.0048(3) -0.0154(3)
N1 0.0373(11) 0.0627(14) 0.0402(11) -0.0131(10) -0.0050(9) -0.0125(10)
N2 0.0397(12) 0.0635(14) 0.0416(12) -0.0125(10) -0.0074(9) -0.0172(10)
O1 0.0389(10) 0.0603(12) 0.0559(11) -0.0209(9) -0.0060(8) -0.0032(8)
N3 0.0353(10) 0.0364(10) 0.0382(10) -0.0055(8) -0.0091(8) -0.0112(8)
C4 0.0506(14) 0.0427(13) 0.0406(13) -0.0112(10) -0.0063(11) -0.0187(11)
N4 0.0410(12) 0.0697(15) 0.0475(12) -0.0206(11) -0.0160(9) -0.0093(11)
C2 0.0396(12) 0.0354(12) 0.0370(12) -0.0039(9) -0.0063(9) -0.0173(9)
C3 0.0403(13) 0.0334(11) 0.0392(12) -0.0048(9) -0.0065(10) -0.0142(10)
C1 0.0404(12) 0.0315(11) 0.0357(12) -0.0029(9) -0.0051(9) -0.0126(9)
C5 0.0685(19) 0.084(2) 0.0422(15) -0.0114(14) -0.0004(13) -0.0369(17)
C8 0.0553(17) 0.0626(18) 0.0592(17) -0.0226(14) 0.0035(13) -0.0127(14)
C7 0.0602(19) 0.135(3) 0.0481(17) -0.0299(19) -0.0074(14) -0.039(2)
C6 0.180(5) 0.0432(18) 0.080(2) -0.0199(17) -0.042(3) -0.028(2)

#===============================================================================

# 10. 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
S1 C1 1.746(2) . ?
S1 C8 1.798(3) . ?
N1 C1 1.298(3) . ?
N1 N2 1.384(3) . ?
N2 C2 1.287(3) . ?
O1 C3 1.213(3) . ?
N3 C1 1.359(3) . ?
N3 C3 1.389(3) . ?
N3 N4 1.408(3) . ?
C4 C5 1.523(4) . ?
C4 C2 1.527(3) . ?
C4 C7 1.528(4) . ?
C4 C6 1.529(4) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
C2 C3 1.465(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

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 S1 C8 100.19(12) . . ?
C1 N1 N2 118.1(2) . . ?
C2 N2 N1 122.0(2) . . ?
C1 N3 C3 121.94(19) . . ?
C1 N3 N4 117.89(19) . . ?
C3 N3 N4 120.03(19) . . ?
C5 C4 C2 109.9(2) . . ?
C5 C4 C7 107.4(3) . . ?
C2 C4 C7 110.1(2) . . ?
C5 C4 C6 109.6(3) . . ?
C2 C4 C6 110.2(2) . . ?
C7 C4 C6 109.5(3) . . ?
N3 N4 H4A 120.0 . . ?
N3 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N2 C2 C3 122.2(2) . . ?
N2 C2 C4 118.6(2) . . ?
C3 C2 C4 119.1(2) . . ?
O1 C3 N3 120.3(2) . . ?
O1 C3 C2 127.2(2) . . ?
N3 C3 C2 112.4(2) . . ?
N1 C1 N3 123.0(2) . . ?
N1 C1 S1 121.36(18) . . ?
N3 C1 S1 115.62(17) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
S1 C8 H8A 109.5 . . ?
S1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
S1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

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
C1 N1 N2 C2 2.4(4) . . . . ?
N1 N2 C2 C3 1.3(4) . . . . ?
N1 N2 C2 C4 -178.6(2) . . . . ?
C5 C4 C2 N2 120.1(3) . . . . ?
C7 C4 C2 N2 2.0(3) . . . . ?
C6 C4 C2 N2 -119.0(3) . . . . ?
C5 C4 C2 C3 -59.8(3) . . . . ?
C7 C4 C2 C3 -177.9(3) . . . . ?
C6 C4 C2 C3 61.2(3) . . . . ?
C1 N3 C3 O1 -174.3(2) . . . . ?
N4 N3 C3 O1 1.4(3) . . . . ?
C1 N3 C3 C2 5.9(3) . . . . ?
N4 N3 C3 C2 -178.37(19) . . . . ?
N2 C2 C3 O1 174.9(2) . . . . ?
C4 C2 C3 O1 -5.2(4) . . . . ?
N2 C2 C3 N3 -5.3(3) . . . . ?
C4 C2 C3 N3 174.59(18) . . . . ?
N2 N1 C1 N3 -1.7(4) . . . . ?
N2 N1 C1 S1 178.71(17) . . . . ?
C3 N3 C1 N1 -2.8(4) . . . . ?
N4 N3 C1 N1 -178.6(2) . . . . ?
C3 N3 C1 S1 176.79(16) . . . . ?
N4 N3 C1 S1 1.0(3) . . . . ?
C8 S1 C1 N1 5.2(2) . . . . ?
C8 S1 C1 N3 -174.38(18) . . . . ?

#===END

data_P1(NEEDLE)
_database_code_depnum_ccdc_archive 'CCDC 252403'

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H14 N4 O S'
_chemical_formula_structural     ?
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_sum            'C8 H14 N4 O S'
_chemical_formula_weight         214.30
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   14.182(9)
_cell_length_b                   9.295(6)
_cell_length_c                   8.723(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.309(10)
_cell_angle_gamma                90
_cell_volume                     1114.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    635
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      25.2
_cell_special_details            
; ?
;

_exptl_crystal_description       needles
_exptl_crystal_colour            'colorless '

_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.267
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# cylinder 'cylindrical'
# empirical 'empirical from intensities'
# gaussian 'Gaussian from crystal shape'
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# refdelf 'refined from delta-F'
# sphere 'spherical'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.8861
_exptl_absorpt_correction_T_max  0.9842

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoKa
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            7988
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         25.35
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_reduction_process 
;
?
;

_reflns_number_total             2031
_reflns_number_gt                1607
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Farrugia, 1999)'
_computing_publication_material  'PLATON (Spek, 1990)'

#===============================================================================

# 8. REFINEMENT DATA

_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^ > 2sigma(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^)+(0.1376P)^2^+0.9326P] 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_extinction_coef       ?
_refine_ls_number_reflns         2031
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1838
_refine_ls_wR_factor_gt          0.1651
_refine_ls_goodness_of_fit_ref   0.817
_refine_ls_restrained_S_all      0.817
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.052

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
S1 S 0.04914(6) 0.43297(9) 0.24732(10) 0.0639(3) Uani 1 1 d . . .
N1 N 0.13275(16) 0.1743(3) 0.2742(3) 0.0536(6) Uani 1 1 d . . .
N3 N 0.20591(18) 0.3530(2) 0.1571(3) 0.0503(6) Uani 1 1 d . . .
N2 N 0.20443(16) 0.0801(3) 0.2550(3) 0.0538(7) Uani 1 1 d . . .
O1 O 0.34440(18) 0.3157(3) 0.0813(3) 0.0788(8) Uani 1 1 d . . .
N4 N 0.2019(3) 0.4984(3) 0.1062(4) 0.0763(9) Uani 1 1 d . . .
H4A H 0.1562 0.5539 0.1199 0.092 Uiso 1 1 calc R . .
H4B H 0.2453 0.5311 0.0615 0.092 Uiso 1 1 calc R . .
C1 C 0.13589(19) 0.3055(3) 0.2272(3) 0.0454(6) Uani 1 1 d . . .
C2 C 0.27461(18) 0.1192(3) 0.1937(3) 0.0429(6) Uani 1 1 d . . .
C3 C 0.2816(2) 0.2666(3) 0.1387(3) 0.0494(7) Uani 1 1 d . . .
C4 C 0.3519(2) 0.0093(3) 0.1833(4) 0.0561(8) Uani 1 1 d . . .
C6 C 0.4512(2) 0.0654(5) 0.2736(4) 0.0781(12) Uani 1 1 d . . .
H6A H 0.4670 0.1504 0.2225 0.117 Uiso 1 1 calc R . .
H6B H 0.4997 -0.0070 0.2750 0.117 Uiso 1 1 calc R . .
H6C H 0.4494 0.0883 0.3801 0.117 Uiso 1 1 calc R . .
C8 C -0.0258(3) 0.3256(4) 0.3410(5) 0.0838(12) Uani 1 1 d . . .
H8A H -0.0573 0.2518 0.2694 0.126 Uiso 1 1 calc R . .
H8B H -0.0741 0.3855 0.3690 0.126 Uiso 1 1 calc R . .
H8C H 0.0139 0.2821 0.4347 0.126 Uiso 1 1 calc R . .
C5 C 0.3523(3) -0.0125(5) 0.0090(5) 0.0891(13) Uani 1 1 d . . .
H5A H 0.2895 -0.0458 -0.0489 0.134 Uiso 1 1 calc R . .
H5B H 0.4008 -0.0825 0.0017 0.134 Uiso 1 1 calc R . .
H5C H 0.3670 0.0771 -0.0348 0.134 Uiso 1 1 calc R . .
C7 C 0.3319(3) -0.1316(5) 0.2555(7) 0.1117(19) Uani 1 1 d . . .
H7A H 0.3305 -0.1162 0.3638 0.167 Uiso 1 1 calc R . .
H7B H 0.3823 -0.1993 0.2512 0.167 Uiso 1 1 calc R . .
H7C H 0.2702 -0.1688 0.1976 0.167 Uiso 1 1 calc R . .

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
S1 0.0707(6) 0.0457(5) 0.0778(6) 0.0016(4) 0.0229(4) 0.0173(4)
N1 0.0400(13) 0.0420(14) 0.0817(17) 0.0084(12) 0.0205(11) 0.0075(10)
N3 0.0672(15) 0.0350(12) 0.0506(12) 0.0035(10) 0.0179(11) 0.0009(11)
N2 0.0393(13) 0.0416(14) 0.0825(17) 0.0118(12) 0.0186(12) 0.0048(10)
O1 0.0816(17) 0.0684(16) 0.1010(18) 0.0258(13) 0.0501(14) 0.0026(13)
N4 0.116(2) 0.0354(14) 0.093(2) 0.0165(14) 0.0557(19) 0.0134(15)
C1 0.0453(15) 0.0415(15) 0.0473(13) 0.0006(11) 0.0075(11) 0.0016(11)
C2 0.0369(13) 0.0442(15) 0.0462(13) 0.0033(11) 0.0075(10) -0.0007(11)
C3 0.0528(16) 0.0496(16) 0.0469(14) 0.0061(12) 0.0142(12) 0.0002(13)
C4 0.0468(16) 0.0540(18) 0.0705(18) 0.0092(15) 0.0201(13) 0.0108(13)
C6 0.0443(18) 0.112(3) 0.076(2) 0.005(2) 0.0102(16) 0.0213(18)
C8 0.062(2) 0.072(3) 0.125(3) 0.015(2) 0.037(2) 0.0227(18)
C5 0.089(3) 0.100(3) 0.077(2) -0.025(2) 0.017(2) 0.021(2)
C7 0.088(3) 0.063(2) 0.208(6) 0.046(3) 0.082(3) 0.037(2)

#===============================================================================

# 10. 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
S1 C1 1.748(3) . ?
S1 C8 1.795(4) . ?
N1 C1 1.291(4) . ?
N1 N2 1.383(3) . ?
N3 C1 1.362(4) . ?
N3 C3 1.382(4) . ?
N3 N4 1.420(3) . ?
N2 C2 1.293(3) . ?
O1 C3 1.213(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
C2 C3 1.463(4) . ?
C2 C4 1.517(4) . ?
C4 C7 1.510(5) . ?
C4 C6 1.526(5) . ?
C4 C5 1.535(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

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 S1 C8 100.35(15) . . ?
C1 N1 N2 118.4(2) . . ?
C1 N3 C3 122.5(2) . . ?
C1 N3 N4 118.2(2) . . ?
C3 N3 N4 119.3(2) . . ?
C2 N2 N1 122.4(2) . . ?
N3 N4 H4A 120.0 . . ?
N3 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N1 C1 N3 122.3(3) . . ?
N1 C1 S1 121.9(2) . . ?
N3 C1 S1 115.8(2) . . ?
N2 C2 C3 121.4(2) . . ?
N2 C2 C4 118.5(3) . . ?
C3 C2 C4 120.1(2) . . ?
O1 C3 N3 120.0(3) . . ?
O1 C3 C2 127.2(3) . . ?
N3 C3 C2 112.8(2) . . ?
C7 C4 C2 110.2(3) . . ?
C7 C4 C6 109.0(3) . . ?
C2 C4 C6 109.1(3) . . ?
C7 C4 C5 110.3(4) . . ?
C2 C4 C5 109.2(3) . . ?
C6 C4 C5 109.1(3) . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
S1 C8 H8A 109.5 . . ?
S1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
S1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?