# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003

data_global
_publ_contact_author_email       Angele.Chiaroni@icsn.cnrs-gif.fr
_publ_contact_author_name        'Angele Chiaroni'
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_coden_Cambridge         177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
C.Roussel
R.Fihi
K.Ciamala
J.Vebrel
T.Zair
C.Riche

data_pnox
_database_code_CSD               167244

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
?
;
_chemical_name_common            PNOX
_chemical_formula_moiety         'C24 H19 N O5'
_chemical_formula_structural     'C24 H19 N O5'
_chemical_formula_analytical     ?
_chemical_formula_sum            'C24 H19 N O5'
_chemical_formula_weight         401.40
_chemical_melting_point          ?
_chemical_compound_source        'chemical synthesis'

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'
N N 0.0311 0.0180 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   9.726(3)
_cell_length_b                   18.482(5)
_cell_length_c                   11.049(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.86(3)
_cell_angle_gamma                90.00
_cell_volume                     1936.3(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      11.8
_cell_measurement_theta_max      17.7

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.100
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Nonius-CAD4 diffractometer'
_diffrn_measurement_method       \q/2\q
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7262
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.66
_diffrn_reflns_theta_max         67.92
_reflns_number_total             3515
_reflns_number_gt                2652
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius CAD4 software 1987'
_computing_cell_refinement       'DATCIN Nonius CAD4 software 1987'
_computing_data_reduction        'NONIUS (Riche, 1989) '
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics    'R3M (Riche,1983) ORTEP(Johnson,1965)'
_computing_publication_material  'SHELXL-93 (Sheldrick, 1993)'

_refine_special_details          
;
Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^
or flagged by the user for potential systematic errors.  Weighted R-factors
wR and all goodnesses 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 observed criterion
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+0.3547P] 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         3513
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_all         0.1188
_refine_ls_wR_factor_ref         0.1022
_refine_ls_goodness_of_fit_all   1.039
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.069
_refine_ls_restrained_S_obs      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/esd_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
O1 O 0.90843(11) 0.67602(6) 0.84316(10) 0.0477(3) Uani 1 d . .
N2 N 0.77744(13) 0.63649(7) 0.83728(12) 0.0461(3) Uani 1 d . .
C3 C 0.7910(2) 0.57339(9) 0.75830(14) 0.0474(4) Uani 1 d . .
H3 H 0.7432(2) 0.53102(9) 0.78302(14) 0.057 Uiso 1 calc R .
C4 C 0.9490(2) 0.55934(10) 0.7756(2) 0.0570(4) Uani 1 d . .
H4A H 0.9760(2) 0.51460(10) 0.8204(2) 0.068 Uiso 1 calc R .
H4B H 0.9757(2) 0.55691(10) 0.6961(2) 0.068 Uiso 1 calc R .
C5 C 1.0164(2) 0.62437(9) 0.85064(14) 0.0469(4) Uani 1 d . .
C6 C 0.7522(2) 0.62735(9) 0.95900(14) 0.0450(4) Uani 1 d . .
C7 C 0.7743(2) 0.68635(10) 1.0392(2) 0.0560(4) Uani 1 d . .
H7 H 0.8125(2) 0.72883(10) 1.0157(2) 0.067 Uiso 1 calc R .
C8 C 0.7396(2) 0.68200(12) 1.1535(2) 0.0641(5) Uani 1 d . .
H8 H 0.7556(2) 0.72151(12) 1.2069(2) 0.077 Uiso 1 calc R .
C9 C 0.6815(2) 0.61970(12) 1.1894(2) 0.0678(5) Uani 1 d . .
H9 H 0.6583(2) 0.61697(12) 1.2665(2) 0.081 Uiso 1 calc R .
C10 C 0.6583(2) 0.56185(12) 1.1097(2) 0.0669(5) Uani 1 d . .
H10 H 0.6185(2) 0.51980(12) 1.1331(2) 0.080 Uiso 1 calc R .
C11 C 0.6933(2) 0.56511(10) 0.9946(2) 0.0564(4) Uani 1 d . .
H11 H 0.6770(2) 0.52542(10) 0.9416(2) 0.068 Uiso 1 calc R .
C12 C 0.7186(2) 0.59811(9) 0.62671(15) 0.0487(4) Uani 1 d . .
O13 O 0.78897(14) 0.62518(8) 0.56025(12) 0.0680(4) Uani 1 d . .
C14 C 0.5633(2) 0.59189(8) 0.58647(13) 0.0444(4) Uani 1 d . .
C15 C 0.4824(2) 0.54616(9) 0.64272(14) 0.0495(4) Uani 1 d . .
H15 H 0.5259(2) 0.51898(9) 0.71146(14) 0.059 Uiso 1 calc R .
C16 C 0.3388(2) 0.54063(9) 0.5978(2) 0.0543(4) Uani 1 d . .
H16 H 0.2863(2) 0.50937(9) 0.6358(2) 0.065 Uiso 1 calc R .
C17 C 0.2721(2) 0.58137(9) 0.4965(2) 0.0533(4) Uani 1 d . .
C18 C 0.3506(2) 0.62681(10) 0.4382(2) 0.0569(4) Uani 1 d . .
H18 H 0.3069(2) 0.65376(10) 0.3693(2) 0.068 Uiso 1 calc R .
C19 C 0.4943(2) 0.63155(9) 0.48371(15) 0.0531(4) Uani 1 d . .
H19 H 0.5467(2) 0.66215(9) 0.44456(15) 0.064 Uiso 1 calc R .
O20 O 0.12973(14) 0.57281(8) 0.46173(14) 0.0761(4) Uani 1 d . .
C21 C 0.0514(2) 0.61985(14) 0.3688(2) 0.0846(7) Uani 1 d . .
H21A H -0.0469(2) 0.60767(14) 0.3537(2) 0.127 Uiso 1 calc R .
H21B H 0.0841(2) 0.61443(14) 0.2935(2) 0.127 Uiso 1 calc R .
H21C H 0.0645(2) 0.66905(14) 0.3969(2) 0.127 Uiso 1 calc R .
O22 O 1.06782(12) 0.60222(6) 0.98001(10) 0.0526(3) Uani 1 d . .
C23 C 1.2079(2) 0.61748(9) 1.01900(15) 0.0495(4) Uani 1 d . .
C24 C 1.2559(2) 0.65237(9) 0.91703(15) 0.0470(4) Uani 1 d . .
C25 C 1.1420(2) 0.65858(8) 0.81754(14) 0.0460(4) Uani 1 d . .
O26 O 1.27123(15) 0.60205(7) 1.12246(11) 0.0671(4) Uani 1 d . .
C27 C 1.3893(2) 0.67642(10) 0.9112(2) 0.0588(5) Uani 1 d . .
H27 H 1.4655(2) 0.67189(10) 0.9786(2) 0.071 Uiso 1 calc R .
C28 C 1.4043(2) 0.70734(10) 0.8013(2) 0.0648(5) Uani 1 d . .
H28 H 1.4927(2) 0.72292(10) 0.7932(2) 0.078 Uiso 1 calc R .
C29 C 1.2894(2) 0.71549(10) 0.7027(2) 0.0662(5) Uani 1 d . .
H29 H 1.3021(2) 0.73763(10) 0.6304(2) 0.079 Uiso 1 calc R .
C30 C 1.1561(2) 0.69159(10) 0.7089(2) 0.0587(5) Uani 1 d . .
H30 H 1.0793(2) 0.69754(10) 0.6425(2) 0.070 Uiso 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
O1 0.0427(6) 0.0451(6) 0.0543(6) -0.0008(5) 0.0091(5) -0.0003(5)
N2 0.0404(7) 0.0493(7) 0.0467(7) -0.0037(6) 0.0058(5) -0.0029(6)
C3 0.0480(10) 0.0482(9) 0.0433(8) -0.0039(6) 0.0046(7) 0.0000(7)
C4 0.0499(10) 0.0529(9) 0.0643(11) -0.0114(8) 0.0043(8) 0.0043(8)
C5 0.0457(9) 0.0496(9) 0.0430(8) 0.0016(7) 0.0047(7) 0.0055(7)
C6 0.0380(8) 0.0515(9) 0.0427(8) -0.0021(7) 0.0031(6) 0.0036(7)
C7 0.0523(11) 0.0586(10) 0.0555(10) -0.0101(8) 0.0087(8) -0.0057(8)
C8 0.0608(12) 0.0771(13) 0.0522(10) -0.0180(9) 0.0076(8) -0.0015(9)
C9 0.0705(13) 0.0875(14) 0.0452(10) -0.0018(9) 0.0122(8) 0.0050(11)
C10 0.0772(14) 0.0709(12) 0.0549(11) 0.0062(9) 0.0196(9) -0.0055(10)
C11 0.0648(12) 0.0531(9) 0.0506(10) -0.0023(7) 0.0115(8) -0.0004(8)
C12 0.0539(10) 0.0491(9) 0.0431(8) -0.0033(7) 0.0112(7) -0.0021(7)
O13 0.0627(9) 0.0851(9) 0.0598(8) 0.0113(7) 0.0211(6) -0.0071(7)
C14 0.0512(10) 0.0468(8) 0.0340(7) -0.0028(6) 0.0071(6) -0.0004(7)
C15 0.0546(10) 0.0516(9) 0.0382(8) 0.0029(7) 0.0018(7) -0.0022(7)
C16 0.0555(11) 0.0543(9) 0.0500(9) 0.0044(7) 0.0051(7) -0.0084(8)
C17 0.0510(10) 0.0523(9) 0.0505(9) -0.0051(7) -0.0015(7) -0.0013(7)
C18 0.0657(12) 0.0563(10) 0.0427(9) 0.0063(7) -0.0007(8) 0.0051(8)
C19 0.0620(11) 0.0552(10) 0.0418(9) 0.0045(7) 0.0106(7) -0.0007(8)
O20 0.0532(8) 0.0794(9) 0.0826(10) 0.0095(7) -0.0129(7) -0.0042(7)
C21 0.0648(13) 0.096(2) 0.0787(14) 0.0062(12) -0.0155(11) 0.0121(12)
O22 0.0524(7) 0.0565(7) 0.0473(6) 0.0078(5) 0.0079(5) -0.0006(5)
C23 0.0519(10) 0.0473(9) 0.0459(9) -0.0028(7) 0.0036(7) 0.0053(7)
C24 0.0449(9) 0.0464(8) 0.0485(9) -0.0041(7) 0.0080(7) 0.0034(7)
C25 0.0470(9) 0.0465(8) 0.0440(8) -0.0016(6) 0.0093(7) 0.0034(7)
O26 0.0756(9) 0.0708(8) 0.0464(7) 0.0032(6) -0.0046(6) 0.0069(7)
C27 0.0489(11) 0.0564(10) 0.0703(12) -0.0116(9) 0.0117(8) 0.0001(8)
C28 0.0617(12) 0.0568(11) 0.0841(14) -0.0128(10) 0.0337(11) -0.0072(9)
C29 0.091(2) 0.0525(10) 0.0672(12) 0.0010(9) 0.0429(11) 0.0004(10)
C30 0.0669(12) 0.0620(11) 0.0493(9) 0.0046(8) 0.0173(8) 0.0078(9)

_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 C5 1.408(2) . ?
O1 N2 1.458(2) . ?
N2 C6 1.430(2) . ?
N2 C3 1.480(2) . ?
C3 C4 1.528(2) . ?
C3 C12 1.537(2) . ?
C4 C5 1.523(2) . ?
C5 O22 1.464(2) . ?
C5 C25 1.491(2) . ?
C6 C11 1.381(2) . ?
C6 C7 1.391(2) . ?
C7 C8 1.380(3) . ?
C8 C9 1.379(3) . ?
C9 C10 1.371(3) . ?
C10 C11 1.389(3) . ?
C12 O13 1.217(2) . ?
C12 C14 1.481(2) . ?
C14 C15 1.391(2) . ?
C14 C19 1.392(2) . ?
C15 C16 1.378(2) . ?
C16 C17 1.384(2) . ?
C17 O20 1.361(2) . ?
C17 C18 1.386(3) . ?
C18 C19 1.379(3) . ?
O20 C21 1.429(2) . ?
O22 C23 1.364(2) . ?
C23 O26 1.206(2) . ?
C23 C24 1.462(2) . ?
C24 C25 1.381(2) . ?
C24 C27 1.387(2) . ?
C25 C30 1.381(2) . ?
C27 C28 1.379(3) . ?
C28 C29 1.383(3) . ?
C29 C30 1.386(3) . ?

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
C5 O1 N2 107.22(11) . . ?
C6 N2 O1 110.40(12) . . ?
C6 N2 C3 121.20(13) . . ?
O1 N2 C3 103.28(12) . . ?
N2 C3 C4 106.22(13) . . ?
N2 C3 C12 103.98(13) . . ?
C4 C3 C12 113.87(15) . . ?
C5 C4 C3 103.48(13) . . ?
O1 C5 O22 109.58(13) . . ?
O1 C5 C25 109.83(13) . . ?
O22 C5 C25 103.75(12) . . ?
O1 C5 C4 106.12(13) . . ?
O22 C5 C4 108.85(13) . . ?
C25 C5 C4 118.55(14) . . ?
C11 C6 C7 119.1(2) . . ?
C11 C6 N2 122.38(14) . . ?
C7 C6 N2 118.2(2) . . ?
C8 C7 C6 120.2(2) . . ?
C9 C8 C7 120.7(2) . . ?
C10 C9 C8 119.0(2) . . ?
C9 C10 C11 121.0(2) . . ?
C6 C11 C10 119.9(2) . . ?
O13 C12 C14 121.6(2) . . ?
O13 C12 C3 119.5(2) . . ?
C14 C12 C3 118.85(14) . . ?
C15 C14 C19 117.8(2) . . ?
C15 C14 C12 123.57(14) . . ?
C19 C14 C12 118.56(15) . . ?
C16 C15 C14 120.83(15) . . ?
C15 C16 C17 120.4(2) . . ?
O20 C17 C16 115.4(2) . . ?
O20 C17 C18 124.7(2) . . ?
C16 C17 C18 119.9(2) . . ?
C19 C18 C17 119.2(2) . . ?
C18 C19 C14 122.0(2) . . ?
C17 O20 C21 118.6(2) . . ?
C23 O22 C5 110.53(13) . . ?
O26 C23 O22 121.0(2) . . ?
O26 C23 C24 130.6(2) . . ?
O22 C23 C24 108.40(13) . . ?
C25 C24 C27 122.0(2) . . ?
C25 C24 C23 108.24(15) . . ?
C27 C24 C23 129.8(2) . . ?
C30 C25 C24 120.8(2) . . ?
C30 C25 C5 130.2(2) . . ?
C24 C25 C5 108.98(14) . . ?
C28 C27 C24 117.2(2) . . ?
C27 C28 C29 120.9(2) . . ?
C28 C29 C30 121.8(2) . . ?
C25 C30 C29 117.3(2) . . ?

_refine_diff_density_max         0.419
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.041