# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2003


data_global

_publ_contact_author_email       TAKU@PH.BUNRI-U.AC.JP

_publ_contact_author_name        'Prof Takumichi Sugihara'
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_audit_creation_method           maXus
_publ_contact_author_address     
;
Faculty of Pharmaceutical Sciences
Tokushima Bunri University
Yamashiro-cho
Tokushima
770-8514
JAPAN
;

_publ_section_title              
;
An Efficient Chemical Fixation of Nitric Oxide:
Convenient and Practical Synthesis of 1,2,3-Oxadiazole 3-Oxides
;

_publ_section_references         
;
Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K.
(1999). maXus  Computer Program for the Solution and Refinement of
Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan
& The University of Glasgow.

Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot
Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge,
Tennessee, USA.

Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L.,
Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R.
(1999). J. Appl. Cryst. 32, 115-119.

Sheldrick, G. M. (1997).  SHELXL97.  Program for the Refinement of Crystal
Structures.  University of Gottingen, Germany.

;

loop_
_publ_author_name
'Takumichi Sugihara'
'Hiroshi Imagawa'
'Kimiko Kuwahara'
'Mugio Nishizawa'
'Hiroko Takao'
;
A.Wakabayashi
;

data_compound_1
_database_code_depnum_ccdc_archive 'CCDC 220238'

_publ_section_abstract           
;
We present the crystal and molecular structure of
;
_publ_section_comment            
;
The study of the titled structure was undertaken to establish its three
dimensional structure.  Geometries are tabulated below.  All diagrams and
calculations were performed using maXus (Bruker Nonius, Delft & MacScience,
Japan).
;

_chemical_compound_source        'Local laboratory'
_exptl_crystal_description       plate
_exptl_crystal_colour            Colourless
_cell_measurement_temperature    298
_refine_ls_hydrogen_treatment    refxyz
_diffrn_measurement_device       'DIP Image plate'
_computing_data_collection       'DIP Image plate'
_computing_data_reduction        'maXus (Mackay et al., 1999)'
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

loop_
_diffrn_radiation_wavelength
0.71073
_diffrn_radiation_wavelength_id  all

_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.00146
_diffrn_orient_matrix_UB_12      0.08370
_diffrn_orient_matrix_UB_13      -0.15716
_diffrn_orient_matrix_UB_21      0.02326
_diffrn_orient_matrix_UB_22      -0.09627
_diffrn_orient_matrix_UB_23      -0.05149
_diffrn_orient_matrix_UB_31      -0.04404
_diffrn_orient_matrix_UB_32      -0.00639
_diffrn_orient_matrix_UB_33      -0.00795

_cell_formula_units_Z            4
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_special_details           
;
?
;
_chemical_formula_weight         220.228
_diffrn_radiation_type           ' MoK\a'

loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
-X,-Y,-Z
'-X,+Y+ 1/2,-Z+ 1/2'
'+X,-Y+ 1/2,+Z+ 1/2'

_symmetry_space_group_name_H-M   'P 21/c        '
_symmetry_cell_setting           Monoclinic
_chemical_formula_moiety         'C11 H12 N2 O3 '
_chemical_formula_sum            'C11 H12 N2 O3 '
_chemical_name_systematic        
;
?
;
_cell_length_a                   5.6130(4)
_cell_length_b                   8.9250(5)
_cell_length_c                   22.154(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.563(3)
_cell_angle_gamma                90.00
_cell_volume                     1104.60(13)
_diffrn_reflns_number            1973
_diffrn_reflns_theta_max         25.78
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_full        25.78
_diffrn_measurement_method       IP
_computing_cell_refinement       Scalepack(HKL)
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

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'

_exptl_absorpt_coefficient_mu    0.098
_reflns_number_total             1863
_reflns_number_gt                1417
_reflns_threshold_expression     >2sigma(I)

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.0881P)^2^+0.1238P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1863
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1580
_refine_ls_wR_factor_gt          0.1412
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
N1 N 0.2762(3) 0.17174(19) 0.51164(8) 0.0784(5) Uani 1 1 d . . .
C2 C 0.8731(4) -0.0575(2) 0.18234(8) 0.0697(5) Uani 1 1 d . . .
O3 O 1.0095(3) -0.08965(19) 0.13600(6) 0.0922(5) Uani 1 1 d . . .
C4 C 0.6115(4) -0.0120(2) 0.28184(9) 0.0724(5) Uani 1 1 d . . .
C5 C 0.2837(4) 0.1031(2) 0.45599(9) 0.0737(5) Uani 1 1 d . . .
C6 C 0.4670(4) 0.1648(2) 0.43143(9) 0.0726(5) Uani 1 1 d . . .
C7 C 0.9407(4) -0.1268(2) 0.23726(9) 0.0785(6) Uani 1 1 d . . .
O8 O 0.5675(3) 0.26679(19) 0.47131(8) 0.1000(6) Uani 1 1 d . . .
C9 C 0.5465(4) 0.0547(2) 0.22634(10) 0.0798(6) Uani 1 1 d . . .
C10 C 0.6751(4) 0.0341(2) 0.17703(9) 0.0764(6) Uani 1 1 d . . .
O11 O 0.1291(3) 0.14538(19) 0.55044(7) 0.1003(6) Uani 1 1 d . . .
C12 C 0.5798(4) 0.1449(2) 0.37425(9) 0.0783(6) Uani 1 1 d . . .
C13 C 0.8125(4) -0.1031(2) 0.28604(9) 0.0776(6) Uani 1 1 d . . .
C14 C 0.4740(4) 0.0163(3) 0.33594(10) 0.0849(6) Uani 1 1 d . . .
C15 C 0.9760(6) -0.0029(3) 0.08279(11) 0.1055(8) Uani 1 1 d . . .
N16 N 0.4443(4) 0.2703(2) 0.52256(9) 0.0999(6) Uani 1 1 d . . .
H5 H 0.1497 0.0168 0.4432 0.088 Uiso 1 1 d R . .
H7 H 1.0767 -0.1924 0.2415 0.094 Uiso 1 1 d R . .
H9 H 0.4054 0.1160 0.2214 0.096 Uiso 1 1 d R . .
H10 H 0.6288 0.0842 0.1394 0.092 Uiso 1 1 d R . .
H12A H 0.5624 0.2348 0.3504 0.094 Uiso 1 1 d R . .
H12B H 0.7467 0.1232 0.3837 0.094 Uiso 1 1 d R . .
H13 H 0.8642 -0.1512 0.3238 0.093 Uiso 1 1 d R . .
H14A H 0.3117 0.0417 0.3220 0.102 Uiso 1 1 d R . .
H14B H 0.4756 -0.0726 0.3604 0.102 Uiso 1 1 d R . .
H15A H 1.0821 -0.0378 0.0543 0.127 Uiso 1 1 d R . .
H15B H 1.0097 0.1004 0.0923 0.127 Uiso 1 1 d R . .
H15C H 0.8133 -0.0125 0.0654 0.127 Uiso 1 1 d 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
N1 0.0870(13) 0.0727(10) 0.0774(10) 0.0007(8) 0.0180(9) 0.0062(9)
C2 0.0723(12) 0.0687(11) 0.0680(11) -0.0031(8) 0.0069(9) -0.0003(9)
O3 0.1005(12) 0.1011(11) 0.0773(9) 0.0025(7) 0.0208(8) 0.0220(9)
C4 0.0704(13) 0.0723(12) 0.0752(12) -0.0049(8) 0.0106(9) -0.0137(9)
C5 0.0769(13) 0.0683(11) 0.0770(12) -0.0002(9) 0.0126(9) 0.0007(9)
C6 0.0744(13) 0.0658(11) 0.0777(12) -0.0010(8) 0.0085(9) 0.0010(9)
C7 0.0737(13) 0.0811(13) 0.0799(13) 0.0051(9) 0.0031(10) 0.0092(10)
O8 0.1053(12) 0.1013(12) 0.0966(11) -0.0220(8) 0.0266(9) -0.0291(9)
C9 0.0746(13) 0.0797(13) 0.0853(14) 0.0007(10) 0.0082(10) 0.0114(10)
C10 0.0820(14) 0.0744(12) 0.0718(12) 0.0057(9) 0.0034(10) 0.0101(10)
O11 0.1161(14) 0.0974(12) 0.0930(11) -0.0042(8) 0.0390(10) -0.0030(9)
C12 0.0774(13) 0.0745(12) 0.0850(13) -0.0008(9) 0.0177(10) -0.0061(10)
C13 0.0790(14) 0.0823(13) 0.0704(11) 0.0092(9) 0.0014(9) -0.0051(10)
C14 0.0810(15) 0.0949(15) 0.0809(13) -0.0082(10) 0.0182(11) -0.0184(11)
C15 0.130(2) 0.1083(18) 0.0826(15) 0.0093(13) 0.0361(14) 0.0091(16)
N16 0.1118(16) 0.1001(14) 0.0907(13) -0.0195(10) 0.0246(11) -0.0216(12)

_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
N1 O11 1.270(2) . ?
N1 N16 1.295(3) . ?
N1 C5 1.381(3) . ?
C2 O3 1.369(2) . ?
C2 C10 1.376(3) . ?
C2 C7 1.384(3) . ?
O3 C15 1.408(3) . ?
C4 C9 1.383(3) . ?
C4 C13 1.387(3) . ?
C4 C14 1.508(3) . ?
C5 C6 1.329(3) . ?
C6 O8 1.353(2) . ?
C6 C12 1.481(3) . ?
C7 C13 1.371(3) . ?
O8 N16 1.386(3) . ?
C9 C10 1.379(3) . ?
C12 C14 1.514(3) . ?
C5 H5 1.0942 . ?
C7 H7 0.9600 . ?
C9 H9 0.9599 . ?
C10 H10 0.9600 . ?
C12 H12A 0.9601 . ?
C12 H12B 0.9600 . ?
C13 H13 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9599 . ?
C15 H15A 0.9601 . ?
C15 H15B 0.9601 . ?
C15 H15C 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
O11 N1 N16 120.59(18) . . ?
O11 N1 C5 126.86(19) . . ?
N16 N1 C5 112.54(18) . . ?
O3 C2 C10 124.48(18) . . ?
O3 C2 C7 116.10(18) . . ?
C10 C2 C7 119.40(19) . . ?
C2 O3 C15 118.28(18) . . ?
C9 C4 C13 117.06(19) . . ?
C9 C4 C14 121.6(2) . . ?
C13 C4 C14 121.35(19) . . ?
C6 C5 N1 105.85(19) . . ?
C5 C6 O8 107.59(18) . . ?
C5 C6 C12 135.45(19) . . ?
O8 C6 C12 116.95(18) . . ?
C13 C7 C2 120.3(2) . . ?
C6 O8 N16 109.88(16) . . ?
C10 C9 C4 122.3(2) . . ?
C2 C10 C9 119.47(19) . . ?
C6 C12 C14 113.16(17) . . ?
C7 C13 C4 121.53(19) . . ?
C4 C14 C12 111.65(17) . . ?
N1 N16 O8 104.13(17) . . ?
C6 C5 H5 136.6 . . ?
N1 C5 H5 117.6 . . ?
C13 C7 H7 119.3 . . ?
C2 C7 H7 120.4 . . ?
C10 C9 H9 118.3 . . ?
C4 C9 H9 119.4 . . ?
C2 C10 H10 120.0 . . ?
C9 C10 H10 120.5 . . ?
C6 C12 H12A 110.0 . . ?
C14 C12 H12A 108.2 . . ?
C6 C12 H12B 109.1 . . ?
C14 C12 H12B 106.9 . . ?
H12A C12 H12B 109.5 . . ?
C7 C13 H13 118.7 . . ?
C4 C13 H13 119.8 . . ?
C4 C14 H14A 109.1 . . ?
C12 C14 H14A 108.0 . . ?
C4 C14 H14B 109.4 . . ?
C12 C14 H14B 109.2 . . ?
H14A C14 H14B 109.5 . . ?
O3 C15 H15A 109.3 . . ?
O3 C15 H15B 109.7 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.3 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.883
_diffrn_measured_fraction_theta_full 0.883
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.071