##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.3
_journal_date_recd_electronic     2006-11-29
_journal_date_accepted     2007-02-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      3
_journal_page_first     o1324
_journal_page_last     o1326
_journal_paper_category     EO
_journal_coeditor_code     FB2035
_publ_contact_author_name     'Erwann Jeanneau'
_publ_contact_author_address
;
Universite Lyon 1
Centre de Diffractometrie Henri Longchambon
43 boulevard du 11 Novembre 1918
69622 Villeurbanne Cedex
France
;
_publ_contact_author_email     erwann.jeanneau@univ-lyon1.fr
_publ_contact_author_fax     '+33 472431160'
_publ_contact_author_phone     '+33 472431859'
_publ_section_title
;\
(1S,2R,2'S,3'aS,5R)-2'-[(1S)-1-\
Hydroxyethyl]-2-isopropyl-5,5'-dimethyl-3',3'a-dihydro-2'H-\
spiro[cyclohexane-1,6'-imidazo[1,5-b]isoxazol]-4'(5'H)-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Aouadi, Kaiss'
;
Université Lyon 1
CPE-Lyon Bâtiment 308
Laboratoire de Chimie Organique 2
UMR--CNRS 5181
43 Boulevard du 11 novembre 1918
F-69622 Villeurbanne
France
;
    'Jeanneau, Erwann'
;
Universtié Lyon 1
Centre de Diffractométrie Henri Longchambon Bâtiment 305
43 boulevard du 11 Novembre 1918
F-69622 Villeurbanne Cedex
France
;
    'Praly, Jean-Pierre'
;
Université Lyon 1
CPE-Lyon Bâtiment 308
Laboratoire de Chimie Organique 2
UMR--CNRS 5181
43 Boulevard du 11 novembre 1918
F-69622 Villeurbanne
France
;
data_I
_chemical_name_systematic
;
(1S,2R,2'S,3'aS,5R)-2'-[(1R)-1-Hydroxyethyl]-2-isopropyl-5,5'-dimethyl-
3',3'a-dihydro-2'H-spiro[cyclohexane-1,6'-imidazo[1,5-b]isoxazol]-4'(5'H)-one
;
_chemical_formula_moiety     'C17 H30 N2 O3'
_chemical_formula_sum     'C17 H30 N2 O3'
_chemical_formula_iupac     'C17 H30 N2 O3'
_chemical_formula_weight     310.43
_symmetry_cell_setting     Tetragonal
_symmetry_space_group_name_H-M     'P 43'
_symmetry_space_group_name_Hall     'P 4cw'
_cell_length_a     10.1670(2)
_cell_length_b     10.1670(2)
_cell_length_c     16.7997(5)
_cell_angle_alpha     90.0
_cell_angle_beta     90.0
_cell_angle_gamma     90.0
_cell_volume     1736.55(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1886
_cell_measurement_theta_min     0.998
_cell_measurement_theta_max     27.878
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.187
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     680
_exptl_absorpt_coefficient_mu     0.081
_exptl_absorpt_correction_type     none
_exptl_absorpt_correction_T_min     1.0
_exptl_absorpt_correction_T_max     1.0
_diffrn_ambient_temperature     293
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_reflns_number     3569
_diffrn_reflns_av_R_equivalents     0.0266
_diffrn_reflns_theta_min     2
_diffrn_reflns_theta_max     27.87
_diffrn_reflns_theta_full     27.87
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_reflns_number_total     2123
_reflns_number_gt     1831
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0587
_refine_ls_R_factor_gt     0.0454
_refine_ls_wR_factor_gt     0.1127
_refine_ls_wR_factor_ref     0.1265
_refine_ls_goodness_of_fit_ref     1.122
_refine_ls_restrained_S_all     1.122
_refine_ls_number_reflns     2123
_refine_ls_number_parameters     205
_refine_ls_number_restraints     1
_refine_ls_number_constraints     30
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0653P)²+0.3501P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_refine_ls_shift/su_max     0
_refine_diff_density_max     0.231
_refine_diff_density_min     -0.237
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_extinction_coef     0.025(5)
_refine_ls_extinction_expression
                                    Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 2001)'
_computing_cell_refinement     'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO/SCALEPACK'
_computing_structure_solution     'SIR97 (Altomare et al.,  1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'DIAMOND (Brandenburg & Putz, 1996)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.8500(3) 0.2965(3) 0.46161(16) 0.0203(6) Uani d . 1 . .
    C C2 0.8562(3) 0.1500(3) 0.47992(17) 0.0224(6) Uani d . 1 . .
    H H21 0.9125 0.1077 0.441 0.034 Uiso calc R 1 . .
    H H22 0.7687 0.113 0.4744 0.034 Uiso calc R 1 . .
    C C3 0.9078(3) 0.1189(3) 0.56328(17) 0.0241(6) Uani d . 1 . .
    H H31 0.9982 0.1517 0.5675 0.036 Uiso calc R 1 . .
    C C4 0.8235(3) 0.1897(3) 0.62491(17) 0.0275(6) Uani d . 1 . .
    H H41 0.735 0.154 0.6237 0.041 Uiso calc R 1 . .
    H H42 0.8595 0.1743 0.6776 0.041 Uiso calc R 1 . .
    C C5 0.8181(3) 0.3368(3) 0.60912(18) 0.0280(6) Uani d . 1 . .
    H H51 0.9057 0.3735 0.6145 0.042 Uiso calc R 1 . .
    H H52 0.7622 0.3783 0.6486 0.042 Uiso calc R 1 . .
    C C6 0.7650(3) 0.3678(3) 0.52548(17) 0.0240(6) Uani d . 1 . .
    H H61 0.6782 0.3261 0.5229 0.036 Uiso calc R 1 . .
    C C7 0.9089(3) -0.0298(3) 0.57835(19) 0.0295(7) Uani d . 1 . .
    H H71 0.8208 -0.0632 0.5749 0.044 Uiso calc R 1 . .
    H H72 0.9437 -0.047 0.6304 0.044 Uiso calc R 1 . .
    H H73 0.9628 -0.0722 0.5391 0.044 Uiso calc R 1 . .
    C C8 0.7400(3) 0.5157(3) 0.51269(19) 0.0301(7) Uani d . 1 . .
    H H81 0.7438 0.5326 0.4553 0.045 Uiso calc R 1 . .
    C C9 0.8411(4) 0.6059(3) 0.5530(2) 0.0407(8) Uani d . 1 . .
    H H91 0.8276 0.6948 0.5357 0.061 Uiso calc R 1 . .
    H H92 0.9283 0.5782 0.5387 0.061 Uiso calc R 1 . .
    H H93 0.8308 0.601 0.6097 0.061 Uiso calc R 1 . .
    C C10 0.6008(4) 0.5510(4) 0.5411(3) 0.0483(10) Uani d . 1 . .
    H H101 0.5913 0.5271 0.5961 0.072 Uiso calc R 1 . .
    H H102 0.5373 0.504 0.5098 0.072 Uiso calc R 1 . .
    H H103 0.5869 0.6438 0.5352 0.072 Uiso calc R 1 . .
    C C11 0.6660(3) 0.2706(3) 0.3555(2) 0.0286(6) Uani d . 1 . .
    H H111 0.6774 0.2031 0.3162 0.043 Uiso calc R 1 . .
    H H112 0.6163 0.3419 0.3331 0.043 Uiso calc R 1 . .
    H H113 0.6197 0.2353 0.4005 0.043 Uiso calc R 1 . .
    C C12 0.8609(3) 0.4083(3) 0.33933(17) 0.0223(6) Uani d . 1 . .
    C C13 0.9820(3) 0.4484(3) 0.38719(17) 0.0221(6) Uani d . 1 . .
    H H131 0.9765 0.5407 0.4035 0.033 Uiso calc R 1 . .
    C C14 1.1095(3) 0.4217(3) 0.34251(18) 0.0247(6) Uani d . 1 . .
    H H141 1.1006 0.4403 0.2861 0.037 Uiso calc R 1 . .
    H H142 1.1819 0.4727 0.3641 0.037 Uiso calc R 1 . .
    C C15 1.1276(3) 0.2765(3) 0.35767(18) 0.0245(6) Uani d . 1 . .
    H H151 1.0711 0.2257 0.3218 0.037 Uiso calc R 1 . .
    C C16 1.2691(3) 0.2271(3) 0.35197(18) 0.0277(6) Uani d . 1 . .
    H H161 1.2731 0.138 0.3741 0.042 Uiso calc R 1 . .
    C C17 1.3146(3) 0.2225(4) 0.2660(2) 0.0393(8) Uani d . 1 . .
    H H171 1.2551 0.1693 0.2355 0.059 Uiso calc R 1 . .
    H H172 1.4013 0.1854 0.2635 0.059 Uiso calc R 1 . .
    H H173 1.3162 0.3101 0.2445 0.059 Uiso calc R 1 . .
    O O1 0.8323(2) 0.4530(2) 0.27319(12) 0.0294(5) Uani d . 1 . .
    O O2 1.08450(19) 0.2598(2) 0.43861(13) 0.0255(5) Uani d . 1 . .
    O O3 1.35480(19) 0.3087(2) 0.39579(15) 0.0322(5) Uani d . 1 . .
    H H25 1.3758 0.2717 0.4372 0.048 Uiso calc R 1 . .
    N N1 0.7950(2) 0.3189(2) 0.38108(14) 0.0216(5) Uani d . 1 . .
    N N2 0.9836(2) 0.3599(2) 0.45768(14) 0.0216(5) Uani d . 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 N1 . 1.481(4) no
    C1 N2 . 1.504(3) no
    C1 C2 . 1.522(4) no
    C1 C6 . 1.557(4) no
    C2 C3 . 1.529(4) no
    C2 H21 . 0.97 no
    C2 H22 . 0.97 no
    C3 C4 . 1.525(4) no
    C3 C7 . 1.532(4) no
    C3 H31 . 0.98 no
    C4 C5 . 1.520(4) no
    C4 H41 . 0.97 no
    C4 H42 . 0.97 no
    C5 C6 . 1.538(4) no
    C5 H51 . 0.97 no
    C5 H52 . 0.97 no
    C6 C8 . 1.539(4) no
    C6 H61 . 0.98 no
    C7 H71 . 0.96 no
    C7 H72 . 0.96 no
    C7 H73 . 0.96 no
    C8 C9 . 1.535(5) no
    C8 C10 . 1.536(4) no
    C8 H81 . 0.98 no
    C9 H91 . 0.96 no
    C9 H92 . 0.96 no
    C9 H93 . 0.96 no
    C10 H101 . 0.96 no
    C10 H102 . 0.96 no
    C10 H103 . 0.96 no
    C11 N1 . 1.465(4) no
    C11 H111 . 0.96 no
    C11 H112 . 0.96 no
    C11 H113 . 0.96 no
    C12 O1 . 1.235(3) no
    C12 N1 . 1.329(4) no
    C12 C13 . 1.526(4) no
    C13 N2 . 1.487(4) no
    C13 C14 . 1.522(4) no
    C13 H131 . 0.98 no
    C14 C15 . 1.509(4) no
    C14 H141 . 0.97 no
    C14 H142 . 0.97 no
    C15 O2 . 1.439(4) no
    C15 C16 . 1.526(4) no
    C15 H151 . 0.98 no
    C16 O3 . 1.411(4) no
    C16 C17 . 1.518(5) no
    C16 H161 . 0.98 no
    C17 H171 . 0.96 no
    C17 H172 . 0.96 no
    C17 H173 . 0.96 no
    O2 N2 . 1.480(3) no
    O3 H25 . 0.82 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 C1 N2 . . 103.6(2) no
    N1 C1 C2 . . 110.5(2) no
    N2 C1 C2 . . 113.0(2) no
    N1 C1 C6 . . 110.4(2) no
    N2 C1 C6 . . 109.4(2) no
    C2 C1 C6 . . 109.8(2) no
    C1 C2 C3 . . 113.7(2) no
    C1 C2 H21 . . 108.8 no
    C3 C2 H21 . . 108.8 no
    C1 C2 H22 . . 108.8 no
    C3 C2 H22 . . 108.8 no
    H21 C2 H22 . . 107.7 no
    C4 C3 C2 . . 109.3(2) no
    C4 C3 C7 . . 110.9(2) no
    C2 C3 C7 . . 111.0(2) no
    C4 C3 H31 . . 108.5 no
    C2 C3 H31 . . 108.5 no
    C7 C3 H31 . . 108.5 no
    C5 C4 C3 . . 111.5(2) no
    C5 C4 H41 . . 109.3 no
    C3 C4 H41 . . 109.3 no
    C5 C4 H42 . . 109.3 no
    C3 C4 H42 . . 109.3 no
    H41 C4 H42 . . 108 no
    C4 C5 C6 . . 111.9(2) no
    C4 C5 H51 . . 109.2 no
    C6 C5 H51 . . 109.2 no
    C4 C5 H52 . . 109.2 no
    C6 C5 H52 . . 109.2 no
    H51 C5 H52 . . 107.9 no
    C5 C6 C8 . . 112.7(2) no
    C5 C6 C1 . . 109.8(2) no
    C8 C6 C1 . . 116.8(2) no
    C5 C6 H61 . . 105.5 no
    C8 C6 H61 . . 105.5 no
    C1 C6 H61 . . 105.5 no
    C3 C7 H71 . . 109.5 no
    C3 C7 H72 . . 109.5 no
    H71 C7 H72 . . 109.5 no
    C3 C7 H73 . . 109.5 no
    H71 C7 H73 . . 109.5 no
    H72 C7 H73 . . 109.5 no
    C9 C8 C10 . . 109.9(3) no
    C9 C8 C6 . . 114.3(3) no
    C10 C8 C6 . . 109.7(3) no
    C9 C8 H81 . . 107.6 no
    C10 C8 H81 . . 107.6 no
    C6 C8 H81 . . 107.6 no
    C8 C9 H91 . . 109.5 no
    C8 C9 H92 . . 109.5 no
    H91 C9 H92 . . 109.5 no
    C8 C9 H93 . . 109.5 no
    H91 C9 H93 . . 109.5 no
    H92 C9 H93 . . 109.5 no
    C8 C10 H101 . . 109.5 no
    C8 C10 H102 . . 109.5 no
    H101 C10 H102 . . 109.5 no
    C8 C10 H103 . . 109.5 no
    H101 C10 H103 . . 109.5 no
    H102 C10 H103 . . 109.5 no
    N1 C11 H111 . . 109.5 no
    N1 C11 H112 . . 109.5 no
    H111 C11 H112 . . 109.5 no
    N1 C11 H113 . . 109.5 no
    H111 C11 H113 . . 109.5 no
    H112 C11 H113 . . 109.5 no
    O1 C12 N1 . . 127.4(3) no
    O1 C12 C13 . . 124.4(3) no
    N1 C12 C13 . . 108.1(2) no
    N2 C13 C14 . . 106.0(2) no
    N2 C13 C12 . . 105.4(2) no
    C14 C13 C12 . . 112.3(2) no
    N2 C13 H131 . . 110.9 no
    C14 C13 H131 . . 110.9 no
    C12 C13 H131 . . 110.9 no
    C15 C14 C13 . . 101.2(2) no
    C15 C14 H141 . . 111.5 no
    C13 C14 H141 . . 111.5 no
    C15 C14 H142 . . 111.5 no
    C13 C14 H142 . . 111.5 no
    H141 C14 H142 . . 109.3 no
    O2 C15 C14 . . 103.8(2) no
    O2 C15 C16 . . 107.9(2) no
    C14 C15 C16 . . 115.2(2) no
    O2 C15 H151 . . 109.9 no
    C14 C15 H151 . . 109.9 no
    C16 C15 H151 . . 109.9 no
    O3 C16 C17 . . 109.0(3) no
    O3 C16 C15 . . 110.8(2) no
    C17 C16 C15 . . 110.9(3) no
    O3 C16 H161 . . 108.7 no
    C17 C16 H161 . . 108.7 no
    C15 C16 H161 . . 108.7 no
    C16 C17 H171 . . 109.5 no
    C16 C17 H172 . . 109.5 no
    H171 C17 H172 . . 109.5 no
    C16 C17 H173 . . 109.5 no
    H171 C17 H173 . . 109.5 no
    H172 C17 H173 . . 109.5 no
    C15 O2 N2 . . 109.53(19) no
    C16 O3 H25 . . 109.5 no
    C12 N1 C11 . . 121.7(2) no
    C12 N1 C1 . . 113.4(2) no
    C11 N1 C1 . . 123.6(2) no
    O2 N2 C13 . . 104.53(19) no
    O2 N2 C1 . . 109.92(19) no
    C13 N2 C1 . . 106.5(2) no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O3 H25 O1 . . 4_665 0.82 1.96 2.763(3) 168 yes
    C3 H31 O2 . . . 0.98 2.58 3.109(4) 114 yes
    C11 H111 O2 . . 2_644 0.96 2.54 3.466(4) 162 yes
    C14 H142 O3 . . . 0.97 2.48 2.887(4) 105 yes
    C8 H81 N1 . . . 0.98 2.56 3.034(4) 110 yes
