data_shelxl 

_database_code_CSD	190377


_journal_coden_Cambridge      188


loop_
_publ_author_name
'Chalier, Florence'
'Tordo, P.'

_publ_contact_author_name     	'Dr Florence Chalier'  
_publ_contact_author_address 
;
UMR 6517 Chimie Biologie et Radicaux libres
Universite de Provence
Structure et Reactivite des Especes
Faculte de Saint Jerome
Av. Escadrille Normandie Niemen
Marseille
Cedex 20
13397
FRANCE
;

_publ_contact_author_email       'CHALIER@SREPIR1.UNIV-MRS.FR'

_publ_requested_journal       'Perkin Transactions 2'


_publ_section_title		
;
2-Diisopropoxyphosphoryl-2-methyl-3,4-dihydro-2H-pyrrole 1-oxide
(DIPPMPO) a crystalline analog of nitrone DEPMPO: synthesis and spin
trapping properties
;

_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
'C11 H22 N O4 P' 
_chemical_formula_weight          263.27 

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' 
'P'  'P'   0.1023   0.0942 
'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' 

_symmetry_cell_setting            monoclinic 
_symmetry_space_group_name_H-M    P21/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                    14.4667(4) 
_cell_length_b                    8.2687(3) 
_cell_length_c                    12.4192(5) 
_cell_angle_alpha                 90.0 
_cell_angle_beta                  91.225(2) 
_cell_angle_gamma                 90.0 
_cell_volume                      1485.32(9) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     2978 
_cell_measurement_theta_min       3 
_cell_measurement_theta_max       26 

_exptl_crystal_description        prism 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           .6 
_exptl_crystal_size_mid           .4 
_exptl_crystal_size_min           .3 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.177 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              568 
_exptl_absorpt_coefficient_mu     0.188 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 

_exptl_special_details 
; 
? 
; 

_diffrn_ambient_temperature       253(2) 
_diffrn_radiation_wavelength      0.71070 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   KappaCCD 
_diffrn_measurement_method        'Phi scans' 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             2978 
_diffrn_reflns_av_R_equivalents   0.045 
_diffrn_reflns_av_sigmaI/netI     0.0286 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        17 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        10 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          3.28 
_diffrn_reflns_theta_max          26.36 
_reflns_number_total              2978 
_reflns_number_gt                 2612 
_reflns_threshold_expression      >2sigma(I) 

_diffrn_measured_fraction_theta_max    0.982 
_diffrn_reflns_theta_full              26.36 
_diffrn_measured_fraction_theta_full   0.982 

_computing_data_collection        'KappaCCD (Nonius, 1998)' 
_computing_cell_refinement        
'Denzo and Scalepak (Otwinowski & Minor, 1997)' 
_computing_data_reduction         
'Denzo and Scalepak (Otwinowski & Minor, 1997)' 
_computing_structure_solution     'SIR (Altamore, 1994)' 
_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^)+(0.0613P)^2^+0.8256P] 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          2978 
_refine_ls_number_parameters      170 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0557 
_refine_ls_R_factor_gt            0.0469 
_refine_ls_wR_factor_ref          0.1285 
_refine_ls_wR_factor_gt           0.1215 
_refine_ls_goodness_of_fit_ref    1.050 
_refine_ls_restrained_S_all       1.050 
_refine_ls_shift/su_max           0.002 
_refine_ls_shift/su_mean          0.000 
_refine_diff_density_max    0.335 
_refine_diff_density_min   -0.347 
_refine_diff_density_rms    0.042 

_publ_section_references
;
Altamore, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C.,
Polidori, G. and Camalli, M. J. Appl. Cryst. (1994) 27, 435-436

Nonius (1998). Kappa CCD Reference Manual. Nonius B.V., P.O. Box 811, 2600
Av, Delft, The Netherlands.

Otwinowski, Z. and Minor, W. " Processing of X-ray Diffraction Data Collected
in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular
Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R.M. Sweet, Eds.,
Academic Press.

Sheldrick, G.M. (1997).  SHELXL97. Program for the refinement of crystal
structures.  Univ. of Gottingen, Germany.
; 

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_symetry_multiplicity 
_atom_site_calc_flag 
_atom_site_refinement_flags 
_atom_site_disorder_assembly 
_atom_site_disorder_group 
P1 P 0.27266(3) 0.40741(6) 0.89898(3) 0.03112(17) Uani 1 1 d . . . 
O2 O 0.29950(10) 0.48652(19) 0.99993(11) 0.0461(4) Uani 1 1 d . . . 
O3 O 0.19824(9) 0.26881(17) 0.90745(12) 0.0436(4) Uani 1 1 d . . . 
O4 O 0.22653(9) 0.52119(17) 0.81204(11) 0.0393(3) Uani 1 1 d . . . 
N5 N 0.44866(11) 0.4025(2) 0.83865(15) 0.0433(4) Uani 1 1 d . . . 
H7 H 0.5746 0.4226 0.9044 0.074(8) Uiso 1 1 d R . . 
O6 O 0.44466(11) 0.5317(2) 0.77906(18) 0.0783(6) Uani 1 1 d . . . 
H8A H 0.3311 0.3453 0.6760 0.067(8) Uiso 1 1 d R . . 
H8B H 0.2828 0.1564 0.7263 0.096(10) Uiso 1 1 d R . . 
H8C H 0.3966 0.1780 0.6929 0.066(7) Uiso 1 1 d R . . 
C7 C 0.51472(13) 0.3563(3) 0.90203(18) 0.0450(5) Uani 1 1 d . . . 
C8 C 0.34311(17) 0.2402(3) 0.72403(17) 0.0547(6) Uani 1 1 d . . . 
H11A H 0.4957 0.2248 1.0383 0.089(10) Uiso 1 1 d R . . 
H11B H 0.5436 0.1234 0.9291 0.094(10) Uiso 1 1 d R . . 
C9 C 0.36637(12) 0.2925(2) 0.83863(14) 0.0340(4) Uani 1 1 d . . . 
H13A H 0.3525 0.1274 0.9736 0.069(8) Uiso 1 1 d R . . 
H13B H 0.4162 0.0474 0.8566 0.094(10) Uiso 1 1 d R . . 
C11 C 0.49387(15) 0.2047(3) 0.95787(18) 0.0523(6) Uani 1 1 d . . . 
H17 H 0.3197 0.7031 0.8261 0.066(8) Uiso 1 1 d R . . 
C13 C 0.39972(14) 0.1532(3) 0.91235(18) 0.0450(5) Uani 1 1 d . . . 
H14 H 0.1104 0.4345 0.9785 0.132(14) Uiso 1 1 d R . . 
C17 C 0.25187(15) 0.6927(3) 0.8008(2) 0.0529(6) Uani 1 1 d . . . 
H19A H 0.2889 0.6565 0.6462 0.108(12) Uiso 1 1 d R . . 
H19B H 0.2656 0.8541 0.6736 0.116(12) Uiso 1 1 d R . . 
H19C H 0.1752 0.6932 0.6534 0.110(12) Uiso 1 1 d R . . 
C14 C 0.10969(15) 0.3025(3) 0.9565(2) 0.0618(7) Uani 1 1 d . . . 
H18A H 0.1099 0.7608 0.8203 0.129(14) Uiso 1 1 d R . . 
H18B H 0.2028 0.9210 0.8487 0.134(14) Uiso 1 1 d R . . 
H18C H 0.1963 0.7543 0.9509 0.133(15) Uiso 1 1 d R . . 
C19 C 0.2487(2) 0.7263(4) 0.6816(3) 0.0839(10) Uani 1 1 d . . . 
H15A H 0.1484 0.2106 1.1012 0.169 Uiso 1 1 d R . . 
H15B H 0.1072 0.0800 1.0223 0.169 Uiso 1 1 d R . . 
H15C H 0.0412 0.2008 1.0805 0.169 Uiso 1 1 d R . . 
C18 C 0.1845(3) 0.7929(3) 0.8628(3) 0.0801(9) Uani 1 1 d . . . 
H16A H 0.0432 0.3548 0.8184 0.173 Uiso 1 1 d R . . 
H16B H -0.0236 0.2916 0.9067 0.173 Uiso 1 1 d R . . 
H16C H 0.0423 0.1708 0.8486 0.173 Uiso 1 1 d R . . 
C15 C 0.1011(3) 0.1880(8) 1.0490(3) 0.134(2) Uani 1 1 d . . . 
C16 C 0.0362(2) 0.2781(9) 0.8758(4) 0.142(2) Uani 1 1 d . . . 

loop_ 
_atom_site_aniso_label 
_atom_site_aniso_U_11 
_atom_site_aniso_U_22 
_atom_site_aniso_U_33 
_atom_site_aniso_U_23 
_atom_site_aniso_U_13 
_atom_site_aniso_U_12 
P1 0.0267(3) 0.0359(3) 0.0308(3) 0.00031(19) 0.00242(16) -0.00272(17) 
O2 0.0492(8) 0.0541(9) 0.0350(7) -0.0072(6) -0.0015(6) -0.0005(7) 
O3 0.0312(7) 0.0424(8) 0.0576(8) 0.0002(7) 0.0125(6) -0.0068(6) 
O4 0.0344(7) 0.0418(8) 0.0416(7) 0.0051(6) -0.0034(5) 0.0003(6) 
N5 0.0275(8) 0.0425(9) 0.0601(11) 0.0130(8) 0.0080(7) -0.0010(7) 
O6 0.0399(9) 0.0682(12) 0.1271(17) 0.0588(12) 0.0085(9) -0.0039(8) 
C7 0.0286(9) 0.0497(12) 0.0567(12) -0.0027(10) 0.0010(8) 0.0001(8) 
C8 0.0559(13) 0.0704(16) 0.0378(11) -0.0115(11) 0.0028(9) 0.0152(12) 
C9 0.0288(8) 0.0383(10) 0.0351(9) 0.0022(8) 0.0036(7) -0.0015(7) 
C11 0.0419(11) 0.0652(14) 0.0496(12) 0.0109(11) -0.0046(9) 0.0051(10) 
C13 0.0394(10) 0.0393(11) 0.0564(12) 0.0104(10) 0.0022(9) 0.0019(8) 
C17 0.0441(11) 0.0430(12) 0.0715(15) 0.0164(11) -0.0006(10) 0.0007(9) 
C14 0.0331(11) 0.0721(17) 0.0812(17) -0.0042(14) 0.0206(11) -0.0074(11) 
C19 0.081(2) 0.089(2) 0.082(2) 0.0431(18) 0.0259(16) 0.0192(17) 
C18 0.100(2) 0.0514(15) 0.089(2) 0.0015(15) 0.0138(17) 0.0173(15) 
C15 0.066(2) 0.249(6) 0.089(2) 0.052(3) 0.0268(18) -0.025(3) 
C16 0.0420(17) 0.265(7) 0.119(3) 0.028(4) -0.0044(18) -0.006(3) 

_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 
P1 O2 1.4594(14) . ? 
P1 O4 1.5701(13) . ? 
P1 O3 1.5774(14) . ? 
P1 C9 1.8294(18) . ? 
O3 C14 1.457(2) . ? 
O4 C17 1.472(3) . ? 
N5 C7 1.283(3) . ? 
N5 O6 1.300(2) . ? 
N5 C9 1.499(2) . ? 
C7 C11 1.467(3) . ? 
C7 H7 1.0247 . ? 
C8 C9 1.518(3) . ? 
C8 H8A 1.0665 . ? 
C8 H8B 1.1154 . ? 
C8 H8C 1.0121 . ? 
C9 C13 1.542(3) . ? 
C11 C13 1.524(3) . ? 
C11 H11A 1.0124 . ? 
C11 H11B 1.0527 . ? 
C13 H13A 1.0547 . ? 
C13 H13B 1.1447 . ? 
C17 C19 1.506(4) . ? 
C17 C18 1.504(4) . ? 
C17 H17 1.0272 . ? 
C14 C16 1.459(5) . ? 
C14 C15 1.496(5) . ? 
C14 H14 1.1259 . ? 
C19 H19A 0.9355 . ? 
C19 H19B 1.0902 . ? 
C19 H19C 1.1454 . ? 
C18 H18A 1.2211 . ? 
C18 H18B 1.1064 . ? 
C18 H18C 1.1482 . ? 
C15 H15A 0.9518 . ? 
C15 H15B 0.9577 . ? 
C15 H15C 0.9633 . ? 
C16 H16A 0.9609 . ? 
C16 H16B 0.9609 . ? 
C16 H16C 0.9537 . ? 

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 
O2 P1 O4 115.06(9) . . ? 
O2 P1 O3 115.96(8) . . ? 
O4 P1 O3 101.57(8) . . ? 
O2 P1 C9 113.51(9) . . ? 
O4 P1 C9 109.72(8) . . ? 
O3 P1 C9 99.36(8) . . ? 
C14 O3 P1 119.77(14) . . ? 
C17 O4 P1 122.65(13) . . ? 
C7 N5 O6 128.13(18) . . ? 
C7 N5 C9 113.60(17) . . ? 
O6 N5 C9 118.24(16) . . ? 
N5 C7 C11 112.74(18) . . ? 
N5 C7 H7 118.4 . . ? 
C11 C7 H7 128.8 . . ? 
C9 C8 H8A 108.8 . . ? 
C9 C8 H8B 108.1 . . ? 
H8A C8 H8B 113.7 . . ? 
C9 C8 H8C 110.3 . . ? 
H8A C8 H8C 108.5 . . ? 
H8B C8 H8C 107.4 . . ? 
N5 C9 C8 109.47(16) . . ? 
N5 C9 C13 102.41(14) . . ? 
C8 C9 C13 113.84(18) . . ? 
N5 C9 P1 106.26(13) . . ? 
C8 C9 P1 112.38(13) . . ? 
C13 C9 P1 111.71(12) . . ? 
C7 C11 C13 104.74(17) . . ? 
C7 C11 H11A 109.0 . . ? 
C13 C11 H11A 114.6 . . ? 
C7 C11 H11B 103.7 . . ? 
C13 C11 H11B 107.9 . . ? 
H11A C11 H11B 115.9 . . ? 
C11 C13 C9 106.11(16) . . ? 
C11 C13 H13A 112.1 . . ? 
C9 C13 H13A 112.3 . . ? 
C11 C13 H13B 104.0 . . ? 
C9 C13 H13B 106.2 . . ? 
H13A C13 H13B 115.3 . . ? 
O4 C17 C19 105.6(2) . . ? 
O4 C17 C18 108.5(2) . . ? 
C19 C17 C18 113.3(2) . . ? 
O4 C17 H17 106.8 . . ? 
C19 C17 H17 107.1 . . ? 
C18 C17 H17 115.0 . . ? 
O3 C14 C16 108.7(3) . . ? 
O3 C14 C15 106.8(3) . . ? 
C16 C14 C15 111.6(3) . . ? 
O3 C14 H14 106.5 . . ? 
C16 C14 H14 107.7 . . ? 
C15 C14 H14 115.3 . . ? 
C17 C19 H19A 110.0 . . ? 
C17 C19 H19B 105.4 . . ? 
H19A C19 H19B 114.3 . . ? 
C17 C19 H19C 105.4 . . ? 
H19A C19 H19C 107.0 . . ? 
H19B C19 H19C 114.3 . . ? 
C17 C18 H18A 103.6 . . ? 
C17 C18 H18B 106.6 . . ? 
H18A C18 H18B 110.6 . . ? 
C17 C18 H18C 104.5 . . ? 
H18A C18 H18C 117.6 . . ? 
H18B C18 H18C 112.7 . . ? 
C14 C15 H15A 109.2 . . ? 
C14 C15 H15B 108.3 . . ? 
H15A C15 H15B 110.3 . . ? 
C14 C15 H15C 109.5 . . ? 
H15A C15 H15C 110.0 . . ? 
H15B C15 H15C 109.5 . . ? 
C14 C16 H16A 109.3 . . ? 
C14 C16 H16B 111.0 . . ? 
H16A C16 H16B 109.2 . . ? 
C14 C16 H16C 107.5 . . ? 
H16A C16 H16C 109.9 . . ? 
H16B C16 H16C 109.9 . . ?