##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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
_journal_date_recd_electronic     2001-06-21
_journal_date_accepted     2001-09-06
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2001
_journal_volume     57
_journal_issue     12
_journal_page_first     1415
_journal_page_last     1417
_journal_paper_category     FO
_publ_contact_author_name     'Dr Marc Rolland'
_publ_contact_author_address
;
Laboratoire des Aminoacides, Peptides et Proteines
Universite Montpellier I et II
Faculte de Pharmacie
UMR CNRS 5810
15 Avenue Charles Flahault
34060 Montpellier CEDEX 2
France
;
_publ_contact_author_email     'rolland@colombes.pharma.univ-montp1.fr'
_publ_contact_author_fax     '00 33 4 67 41 20 17'
_publ_contact_author_phone     '00 33 4 67 54 86 51'
_publ_section_title
;
Full stereochemical understanding in a new (2R,3R,4R)-4-hydroxyisoleucine
synthesis
;
loop_
    _publ_author_name
    _publ_author_address
    'Rolland, Marc'
;
Laboratoire des Aminoacides, Peptides et Protéines
Université Montpellier I et II
Faculté de Pharmacie
UMR CNRS 5810
15 Avenue Charles Flahault
34060 Montpellier CEDEX 2
France
;
    'Kassem, Tarek'
;
Laboratoire des Aminoacides, Peptides et Protéines
Université Montpellier I et II
Faculté de Pharmacie
UMR CNRS 5810
15 Avenue Charles Flahault
34060 Montpellier CEDEX 2
France
;
    "Rolland, Valérie"
;
Laboratoire des Aminoacides, Peptides et Protéines
Université Montpellier I et II
Faculté de Pharmacie
UMR CNRS 5810
15 Avenue Charles Flahault
34060 Montpellier CEDEX 2
France
;
    'Martinez, Jean'
;
Laboratoire des Aminoacides, Peptides et Protéines
Université Montpellier I et II
Faculté de Pharmacie
UMR CNRS 5810
15 Avenue Charles Flahault
34060 Montpellier CEDEX 2
France
;
data_III
_chemical_name_systematic
;
2,3,5,6,7,8-Hexahydro-6,8-methano-7,7,8a-trimethyl-3-(1-methyl-2-
oxopropylidene)-5H-1,4-benzoxazin-2-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H21 N O3'
_chemical_formula_sum     'C16 H21 N O3'
_chemical_formula_iupac     'C16 H21 N O3'
_chemical_formula_weight     275.34
_symmetry_cell_setting     'Orthorhombic'
_symmetry_space_group_name_H-M     'P212121'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     8.4160(3)
_cell_length_b     12.3127(5)
_cell_length_c     14.7039(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1523.72(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     10878
_cell_measurement_theta_min     1.00
_cell_measurement_theta_max     26.44
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max      .4
_exptl_crystal_size_mid      .3
_exptl_crystal_size_min      .2
_exptl_crystal_density_diffrn     1.200
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     592
_exptl_absorpt_coefficient_mu      .082
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'X-ray tube'
_diffrn_measurement_device     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     'φ-scan'
_diffrn_reflns_number     10878
_diffrn_reflns_av_R_equivalents      .033
_diffrn_reflns_av_sigmaI/netI      .023
_diffrn_reflns_theta_min     3.31
_diffrn_reflns_theta_max     26.44
_diffrn_reflns_theta_full     26.44
_diffrn_measured_fraction_theta_max      .980
_diffrn_measured_fraction_theta_full      .980
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_refine_special_details
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F², conventional R-factors R are based
  on F, with F set to zero for negative F². The threshold expression of
  F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
  not relevant to the choice of reflections for refinement.  R-factors based
  on F² are statistically about twice as large as those based on F, and R-
  factors based on ALL data will be even larger.
;
_reflns_number_total     1775
_reflns_number_gt     1668
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .041
_refine_ls_R_factor_gt      .038
_refine_ls_wR_factor_gt      .098
_refine_ls_wR_factor_ref      .100
_refine_ls_goodness_of_fit_ref     1.058
_refine_ls_restrained_S_all     1.058
_refine_ls_number_reflns     1775
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0551P)²+0.1091P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .13
_refine_diff_density_min      -.16
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N'  .0061  .0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'KappaCCD Reference Manual (Nonius, 1998)'
_computing_data_reduction     'DENZO and SCALEPAK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEPII (Johnson, 1976)'
_computing_publication_material     'MAXUS (Mackay et al., 1999)'
loop_
    _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
    _atom_site_type_symbol
    O1  -.0355(2)  .61400(17)  .53152(14)  .0809(6) Uani d . 1 . . O
    O2  .1157(2)  .54369(11)  .71948(10)  .0560(4) Uani d . 1 . . O
    O3  .16674(16)  .36925(9)  .73540(8)  .0442(3) Uani d . 1 . . O
    N1  .3561(2)  .37272(13)  .58021(11)  .0495(4) Uani d . 1 . . N
    C1  .1678(2)  .46121(14)  .68663(12)  .0408(4) Uani d . 1 . . C
    C2  .2433(2)  .45510(15)  .59522(12)  .0427(4) Uani d . 1 . . C
    C3  .2174(3)  .53378(16)  .53378(13)  .0489(5) Uani d . 1 . . C
    C4  .1034(3)  .62506(17)  .54936(14)  .0530(5) Uani d . 1 . . C
    C5  .1713(4)  .73112(18)  .5795(2)  .0805(8) Uani d . 1 . . C
    C6  .2937(4)  .5352(2)  .44169(17)  .0825(9) Uani d . 1 . . C
    C7  .1963(2)  .26619(14)  .68705(12)  .0384(4) Uani d . 1 . . C
    C8  .3392(2)  .28487(15)  .62532(13)  .0445(4) Uani d . 1 . . C
    C9  .4713(3)  .2018(2)  .62734(18)  .0622(6) Uani d . 1 . . C
    C10  .4679(3)  .1384(2)  .71647(18)  .0621(6) Uani d . 1 . . C
    C11  .4121(3)  .2148(2)  .79336(16)  .0607(6) Uani d . 1 . . C
    C12  .2411(2)  .18707(15)  .76226(14)  .0463(4) Uani d . 1 . . C
    C13  .3078(3)  .07631(17)  .72646(17)  .0586(5) Uani d . 1 . . C
    C14  .2422(4)  .0191(2)  .6446(2)  .0829(8) Uani d . 1 . . C
    C15  .3131(4)  -.0056(2)  .8054(2)  .0939(10) Uani d . 1 . . C
    C16  .0437(3)  .24001(18)  .63723(16)  .0539(5) Uani d . 1 . . C
    H5A  .0874  .7835  .5856  .121 Uiso calc R 1 . . H
    H5B  .2467  .7562  .5353  .121 Uiso calc R 1 . . H
    H5C  .2235  .7219  .6371  .121 Uiso calc R 1 . . H
    H6A  .3272  .6077  .4275  .124 Uiso calc R 1 . . H
    H6B  .2187  .5109  .3969  .124 Uiso calc R 1 . . H
    H6C  .3843  .4878  .4417  .124 Uiso calc R 1 . . H
    H9A  .5730  .2381  .6210  .075 Uiso calc R 1 . . H
    H9B  .4592  .1521  .5767  .075 Uiso calc R 1 . . H
    H10  .5636  .0958  .7298  .074 Uiso calc R 1 . . H
    H11A  .4416  .2903  .7849  .073 Uiso calc R 1 . . H
    H11B  .4380  .1897  .8541  .073 Uiso calc R 1 . . H
    H12  .1632  .1809  .8115  .056 Uiso calc R 1 . . H
    H14A  .3052  -.0441  .6319  .124 Uiso calc R 1 . . H
    H14B  .2449  .0672  .5932  .124 Uiso calc R 1 . . H
    H14C  .1345  -.0023  .6563  .124 Uiso calc R 1 . . H
    H15A  .2071  -.0286  .8198  .141 Uiso calc R 1 . . H
    H15B  .3601  .0281  .8577  .141 Uiso calc R 1 . . H
    H15C  .3754  -.0674  .7879  .141 Uiso calc R 1 . . H
    H16A  -.0371  .2208  .6804  .081 Uiso calc R 1 . . H
    H16B  .0614  .1802  .5966  .081 Uiso calc R 1 . . H
    H16C  .0100  .3024  .6031  .081 Uiso calc R 1 . . H
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
    O1 C4 . 1.205(3) yes
    O2 C1 . 1.207(2) yes
    O3 C1 . 1.340(2) yes
    O3 C7 . 1.476(2) yes
    N1 C8 . 1.277(2) yes
    N1 C2 . 1.407(2) yes
    C1 C2 . 1.488(2) yes
    C2 C3 . 1.342(3) yes
    C3 C4 . 1.495(3) yes
    C3 C6 . 1.499(3) yes
    C4 C5 . 1.493(3) yes
    C7 C8 . 1.524(3) yes
    C8 C9 . 1.511(3) no
    C9 C10 . 1.526(4) no
    C7 C16 . 1.513(3) no
    C7 C12 . 1.521(3) no
    C10 C11 . 1.544(3) no
    C10 C13 . 1.556(3) no
    C11 C12 . 1.547(3) no
    C12 C13 . 1.566(3) no
    C13 C14 . 1.500(4) no
    C13 C15 . 1.538(3) no
    C5 H5A .  .9600 no
    C5 H5B .  .9600 no
    C5 H5C .  .9600 no
    C6 H6A .  .9600 no
    C6 H6B .  .9600 no
    C6 H6C .  .9600 no
    C10 H10 .  .9800 no
    C9 H9A .  .9700 no
    C9 H9B .  .9700 no
    C11 H11A .  .9700 no
    C11 H11B .  .9700 no
    C12 H12 .  .9800 no
    C14 H14A .  .9600 no
    C14 H14B .  .9600 no
    C14 H14C .  .9600 no
    C15 H15A .  .9600 no
    C15 H15B .  .9600 no
    C15 H15C .  .9600 no
    C16 H16A .  .9600 no
    C16 H16B .  .9600 no
    C16 H16C .  .9600 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
    C1 O3 C7 . . 117.87(12) yes
    C8 N1 C2 . . 117.02(15) yes
    O2 C1 O3 . . 119.63(15) yes
    O2 C1 C2 . . 123.97(17) yes
    O3 C1 C2 . . 116.31(15) yes
    C3 C2 N1 . . 121.62(17) yes
    C3 C2 C1 . . 120.13(17) yes
    N1 C2 C1 . . 117.79(16) yes
    C2 C3 C4 . . 122.92(17) yes
    C2 C3 C6 . . 123.1(2) yes
    C4 C3 C6 . . 113.88(19) yes
    O1 C4 C5 . . 122.3(2) yes
    O1 C4 C3 . . 120.2(2) yes
    C5 C4 C3 . . 117.2(2) yes
    O3 C7 C16 . . 105.88(15) no
    O3 C7 C12 . . 104.02(13) no
    C16 C7 C12 . . 115.22(16) no
    O3 C7 C8 . . 106.86(14) yes
    C16 C7 C8 . . 114.43(16) no
    C12 C7 C8 . . 109.48(15) no
    N1 C8 C9 . . 120.11(18) no
    N1 C8 C7 . . 121.67(16) yes
    C9 C8 C7 . . 117.83(16) no
    C8 C9 C10 . . 110.45(18) no
    C9 C10 C11 . . 108.82(18) no
    C9 C10 C13 . . 110.4(2) no
    C11 C10 C13 . . 88.08(18) no
    C10 C11 C12 . . 86.11(16) no
    C7 C12 C11 . . 107.71(17) no
    C7 C12 C13 . . 113.73(17) no
    C11 C12 C13 . . 87.61(16) no
    C14 C13 C15 . . 107.9(2) no
    C14 C13 C10 . . 118.3(2) no
    C15 C13 C10 . . 111.6(2) no
    C14 C13 C12 . . 123.1(2) no
    C15 C13 C12 . . 109.1(2) no
    C10 C13 C12 . . 85.10(16) no
    C4 C5 H5A . . 109.5 no
    C4 C5 H5B . . 109.5 no
    H5A C5 H5B . . 109.5 no
    C4 C5 H5C . . 109.5 no
    H5A C5 H5C . . 109.5 no
    H5B C5 H5C . . 109.5 no
    C3 C6 H6A . . 109.5 no
    C3 C6 H6B . . 109.5 no
    H6A C6 H6B . . 109.5 no
    C3 C6 H6C . . 109.5 no
    H6A C6 H6C . . 109.5 no
    H6B C6 H6C . . 109.5 no
    C8 C9 H9A . . 109.6 no
    C10 C9 H9A . . 109.6 no
    C8 C9 H9B . . 109.6 no
    C10 C9 H9B . . 109.6 no
    H9A C9 H9B . . 108.1 no
    C9 C10 H10 . . 115.4 no
    C11 C10 H10 . . 115.4 no
    C13 C10 H10 . . 115.4 no
    C11 C12 H12 . . 114.9 no
    C13 C12 H12 . . 114.9 no
    C10 C11 H11A . . 114.3 no
    C12 C11 H11A . . 114.3 no
    C10 C11 H11B . . 114.3 no
    C12 C11 H11B . . 114.3 no
    H11A C11 H11B . . 111.4 no
    C7 C12 H12 . . 114.9 no
    C13 C14 H14A . . 109.5 no
    C13 C14 H14B . . 109.5 no
    H14A C14 H14B . . 109.5 no
    C13 C14 H14C . . 109.5 no
    H14A C14 H14C . . 109.5 no
    H14B C14 H14C . . 109.5 no
    C13 C15 H15A . . 109.5 no
    C13 C15 H15B . . 109.5 no
    H15A C15 H15B . . 109.5 no
    C13 C15 H15C . . 109.5 no
    H15A C15 H15C . . 109.5 no
    H15B C15 H15C . . 109.5 no
    C7 C16 H16A . . 109.5 no
    C7 C16 H16B . . 109.5 no
    H16A C16 H16B . . 109.5 no
    C7 C16 H16C . . 109.5 no
    H16A C16 H16C . . 109.5 no
    H16B C16 H16C . . 109.5 no
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C7 O3 C1 O2 . . . . 166.26(18) no
    C7 O3 C1 C2 . . . . -17.0(2) no
    C8 N1 C2 C3 . . . . -158.28(19) yes
    C8 N1 C2 C1 . . . . 29.6(3) no
    O2 C1 C2 C3 . . . . -19.2(3) no
    O3 C1 C2 C3 . . . . 164.23(18) yes
    O2 C1 C2 N1 . . . . 153.1(2) no
    O3 C1 C2 N1 . . . . -23.5(2) no
    N1 C2 C3 C4 . . . . -177.34(19) no
    C1 C2 C3 C4 . . . . -5.4(3) yes
    N1 C2 C3 C6 . . . . 5.8(3) no
    C1 C2 C3 C6 . . . . 177.8(2) no
    C2 C3 C4 O1 . . . . -85.9(3) yes
    C6 C3 C4 O1 . . . . 91.2(3) no
    C2 C3 C4 C5 . . . . 99.3(3) yes
    C6 C3 C4 C5 . . . . -83.6(3) no
    C1 O3 C7 C16 . . . . -76.3(2) no
    C1 O3 C7 C12 . . . . 161.85(16) no
    C1 O3 C7 C8 . . . . 46.1(2) no
    C2 N1 C8 C9 . . . . -167.9(2) no
    C2 N1 C8 C7 . . . . 4.7(3) no
    O3 C7 C8 N1 . . . . -41.3(2) no
    C16 C7 C8 N1 . . . . 75.5(2) no
    C12 C7 C8 N1 . . . . -153.39(18) no
    O3 C7 C8 C9 . . . . 131.52(18) no
    C16 C7 C8 C9 . . . . -111.6(2) no
    C12 C7 C8 C9 . . . . 19.5(2) no
    N1 C8 C9 C10 . . . . 150.7(2) no
    C7 C8 C9 C10 . . . . -22.3(3) no
    C8 C9 C10 C11 . . . . -34.0(3) no
    C8 C9 C10 C13 . . . . 61.1(2) no
    C9 C10 C11 C12 . . . . 83.8(2) no
    C13 C10 C11 C12 . . . . -27.10(16) no
    O3 C7 C12 C11 . . . . -74.35(18) no
    C16 C7 C12 C11 . . . . 170.23(17) no
    C8 C7 C12 C11 . . . . 39.6(2) no
    O3 C7 C12 C13 . . . . -169.66(15) no
    C16 C7 C12 C13 . . . . 74.9(2) no
    C8 C7 C12 C13 . . . . -55.7(2) no
    C10 C11 C12 C7 . . . . -87.25(18) no
    C10 C11 C12 C13 . . . . 26.92(17) no
    C9 C10 C13 C14 . . . . 42.6(3) no
    C11 C10 C13 C14 . . . . 152.0(2) no
    C9 C10 C13 C15 . . . . 168.8(2) no
    C11 C10 C13 C15 . . . . -81.9(2) no
    C9 C10 C13 C12 . . . . -82.6(2) no
    C11 C10 C13 C12 . . . . 26.79(16) no
    C7 C12 C13 C14 . . . . -39.2(3) no
    C11 C12 C13 C14 . . . . -147.5(2) no
    C7 C12 C13 C15 . . . . -167.2(2) no
    C11 C12 C13 C15 . . . . 84.4(2) no
    C7 C12 C13 C10 . . . . 81.6(2) no
    C11 C12 C13 C10 . . . . -26.74(17) no
data_V
_chemical_name_systematic
;
2,3,5,6,7,8-Hexahydro-3-(2-hydroxy-1-methylpropyl)-6,8-methano-7,7,8a-
trimethyl-5H-1,4-benzoxazin-2-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H25 N O3'
_chemical_formula_sum     'C16 H25 N O3'
_chemical_formula_iupac     'C16 H25 N O3'
_chemical_formula_weight     279.37
_symmetry_cell_setting     'Orthorhombic'
_symmetry_space_group_name_H-M     'P212121'
loop_
    _symmetry_equiv_pos_as_xyz
    '+X,+Y,+Z'
    '-X+ 1/2,-Y,+Z+ 1/2'
    '+X+ 1/2,-Y+ 1/2,-Z'
    '-X,+Y+ 1/2,-Z+ 1/2'
_cell_length_a     10.2905(3)
_cell_length_b     11.8864(5)
_cell_length_c     12.8317(5)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1569.50(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     11088
_cell_measurement_theta_min     1.00
_cell_measurement_theta_max     26.34
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max      .4
_exptl_crystal_size_mid      .3
_exptl_crystal_size_min      .2
_exptl_crystal_density_diffrn     1.182
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     608
_exptl_absorpt_coefficient_mu      .081
_exptl_absorpt_correction_type     'none'
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
  ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'X-ray tube'
_diffrn_measurement_device     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     'φ-scan'
_diffrn_reflns_number     11088
_diffrn_reflns_av_R_equivalents      .036
_diffrn_reflns_av_sigmaI/netI      .024
_diffrn_reflns_theta_min     3.06
_diffrn_reflns_theta_max     26.34
_diffrn_reflns_theta_full     26.34
_diffrn_measured_fraction_theta_max      .976
_diffrn_measured_fraction_theta_full      .976
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_refine_special_details
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F², conventional R-factors R are based
  on F, with F set to zero for negative F². The threshold expression of
  F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
  not relevant to the choice of reflections for refinement.  R-factors based
  on F² are statistically about twice as large as those based on F, and R-
  factors based on ALL data will be even larger.
;
_reflns_number_total     1791
_reflns_number_gt     1638
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .041
_refine_ls_R_factor_gt      .038
_refine_ls_wR_factor_gt      .098
_refine_ls_wR_factor_ref      .100
_refine_ls_goodness_of_fit_ref     1.058
_refine_ls_restrained_S_all     1.058
_refine_ls_number_reflns     1791
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0677P)²+0.1278P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .13
_refine_diff_density_min      -.12
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N'  .0061  .0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'KappaCCD Reference Manual (Nonius, 1998)'
_computing_data_reduction     'DENZO and SCALEPAK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEPII (Johnson, 1976)'
_computing_publication_material     'MAXUS (Mackay et al., 1999)'
loop_
    _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
    _atom_site_type_symbol
    O1  .42623(16)  .73053(16)  .57239(13)  .0716(5) Uani d . 1 . . O
    O2  .72659(16) 1.05251(14)  .44797(14)  .0734(5) Uani d . 1 . . O
    O3  .63837(14) 1.00686(11)  .29869(11)  .0556(4) Uani d . 1 . . O
    N1  .50368(15)  .82874(13)  .38796(13)  .0496(4) Uani d . 1 . . N
    C1  .66693(18)  .98389(17)  .39881(17)  .0533(5) Uani d . 1 . . C
    C2  .61678(16)  .87394(15)  .44380(15)  .0464(4) Uani d . 1 . . C
    C3  .58141(17)  .88756(16)  .56013(15)  .0485(4) Uani d . 1 . . C
    C4  .54706(19)  .77388(18)  .60934(17)  .0549(5) Uani d . 1 . . C
    C5  .5371(3)  .7795(3)  .72699(18)  .0731(7) Uani d . 1 . . C
    C6  .4750(2)  .9749(2)  .57512(19)  .0690(6) Uani d . 1 . . C
    C7  .59405(18)  .91485(15)  .23041(15)  .0471(4) Uani d . 1 . . C
    C8  .49354(17)  .84735(14)  .29143(15)  .0463(4) Uani d . 1 . . C
    C9  .3705(2)  .8141(2)  .23492(17)  .0597(5) Uani d . 1 . . C
    C10  .3425(2)  .89586(19)  .14670(19)  .0628(5) Uani d . 1 . . C
    C11  .3903(2) 1.0134(2)  .1794(2)  .0685(6) Uani d . 1 . . C
    C12  .5264(2)  .97498(17)  .14047(16)  .0535(5) Uani d . 1 . . C
    C13  .4521(2)  .89393(18)  .06422(16)  .0572(5) Uani d . 1 . . C
    C14  .4139(3)  .9582(2)  -.0349(2)  .0837(8) Uani d . 1 . . C
    C15  .5060(3)  .78096(19)  .0297(2)  .0701(6) Uani d . 1 . . C
    C16  .71463(19)  .8475(2)  .20144(18)  .0631(6) Uani d . 1 . . C
    H1  .4199  .7424  .5097  .086 Uiso calc R 1 . . H
    H2  .6869  .8184  .4389  .056 Uiso calc R 1 . . H
    H3  .6591  .9156  .5959  .058 Uiso calc R 1 . . H
    H4  .6156  .7200  .5913  .066 Uiso calc R 1 . . H
    H5A  .5288  .7048  .7546  .110 Uiso calc R 1 . . H
    H5B  .4623  .8231  .7462  .110 Uiso calc R 1 . . H
    H5C  .6139  .8142  .7548  .110 Uiso calc R 1 . . H
    H6A  .5027 1.0454  .5462  .103 Uiso calc R 1 . . H
    H6B  .4577  .9840  .6482  .103 Uiso calc R 1 . . H
    H6C  .3973  .9504  .5404  .103 Uiso calc R 1 . . H
    H9A  .2982  .8138  .2835  .072 Uiso calc R 1 . . H
    H9B  .3799  .7387  .2070  .072 Uiso calc R 1 . . H
    H10  .2539  .8931  .1188  .075 Uiso calc R 1 . . H
    H11A  .3857 1.0276  .2538  .082 Uiso calc R 1 . . H
    H11B  .3527 1.0747  .1397  .082 Uiso calc R 1 . . H
    H12  .5781 1.0337  .1064  .064 Uiso calc R 1 . . H
    H14A  .3798 1.0306  -.0163  .126 Uiso calc R 1 . . H
    H14B  .3489  .9164  -.0721  .126 Uiso calc R 1 . . H
    H14C  .4890  .9677  -.0784  .126 Uiso calc R 1 . . H
    H15A  .5203  .7343  .0897  .105 Uiso calc R 1 . . H
    H15B  .5868  .7922  -.0062  .105 Uiso calc R 1 . . H
    H15C  .4451  .7450  -.0161  .105 Uiso calc R 1 . . H
    H16A  .7663  .8899  .1531  .095 Uiso calc R 1 . . H
    H16B  .6890  .7777  .1699  .095 Uiso calc R 1 . . H
    H16C  .7646  .8325  .2631  .095 Uiso calc R 1 . . H
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
    O1 C4 . 1.427(2) yes
    O2 C1 . 1.200(2) yes
    O3 C1 . 1.346(3) yes
    O3 C7 . 1.474(2) yes
    N1 C8 . 1.262(2) yes
    N1 C2 . 1.468(2) yes
    C1 C2 . 1.519(3) yes
    C2 C3 . 1.545(3) yes
    C3 C6 . 1.521(3) yes
    C3 C4 . 1.533(3) yes
    C4 C5 . 1.515(3) yes
    C7 C16 . 1.522(3) no
    C7 C8 . 1.525(2) yes
    C7 C12 . 1.526(3) no
    C8 C9 . 1.512(3) no
    C9 C10 . 1.520(3) no
    C10 C11 . 1.539(3) no
    C10 C13 . 1.547(3) no
    C11 C12 . 1.555(3) no
    C12 C13 . 1.571(3) no
    C13 C15 . 1.519(3) no
    C13 C14 . 1.535(3) no
    O1 H1 .  .8200 no
    C2 H2 .  .9800 no
    C3 H3 .  .9800 no
    C4 H4 .  .9800 no
    C5 H5A .  .9600 no
    C5 H5B .  .9600 no
    C5 H5C .  .9600 no
    C6 H6A .  .9600 no
    C6 H6B .  .9600 no
    C6 H6C .  .9600 no
    C9 H9A .  .9700 no
    C9 H9B .  .9700 no
    C10 H10 .  .9800 no
    C11 H11A .  .9700 no
    C11 H11B .  .9700 no
    C12 H12 .  .9800 no
    C14 H14A .  .9600 no
    C14 H14B .  .9600 no
    C14 H14C .  .9600 no
    C15 H15A .  .9600 no
    C15 H15B .  .9600 no
    C15 H15C .  .9600 no
    C16 H16A .  .9600 no
    C16 H16B .  .9600 no
    C16 H16C .  .9600 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
    C1 O3 C7 . . 118.99(15) yes
    C8 N1 C2 . . 118.69(16) yes
    O2 C1 O3 . . 118.40(18) yes
    O2 C1 C2 . . 123.97(19) yes
    O3 C1 C2 . . 117.58(16) yes
    N1 C2 C1 . . 113.49(16) yes
    N1 C2 C3 . . 108.85(14) yes
    C1 C2 C3 . . 110.92(16) yes
    C6 C3 C4 . . 112.55(16) yes
    C6 C3 C2 . . 111.30(17) yes
    C4 C3 C2 . . 111.10(16) yes
    O1 C4 C5 . . 106.75(19) yes
    O1 C4 C3 . . 112.48(17) yes
    C5 C4 C3 . . 112.8(2) yes
    O3 C7 C16 . . 106.44(16) no
    O3 C7 C8 . . 107.15(15) yes
    C16 C7 C8 . . 113.67(16) no
    O3 C7 C12 . . 104.09(14) no
    C16 C7 C12 . . 115.68(17) no
    C8 C7 C12 . . 108.99(16) no
    N1 C8 C9 . . 119.60(17) no
    N1 C8 C7 . . 122.67(17) yes
    C9 C8 C7 . . 117.34(17) no
    C8 C9 C10 . . 110.42(17) no
    C9 C10 C11 . . 108.45(19) no
    C9 C10 C13 . . 111.21(18) no
    C11 C10 C13 . . 88.08(18) no
    C10 C11 C12 . . 86.24(16) no
    C7 C12 C11 . . 107.77(18) no
    C7 C12 C13 . . 113.94(16) no
    C11 C12 C13 . . 86.68(16) no
    C15 C13 C14 . . 107.0(2) no
    C15 C13 C10 . . 118.61(19) no
    C14 C13 C10 . . 111.9(2) no
    C15 C13 C12 . . 123.07(18) no
    C14 C13 C12 . . 109.62(18) no
    C10 C13 C12 . . 85.40(16) no
    C4 O1 H1 . . 109.5 no
    N1 C2 H2 . . 107.8 no
    C1 C2 H2 . . 107.8 no
    C3 C2 H2 . . 107.8 no
    C6 C3 H3 . . 107.2 no
    C4 C3 H3 . . 107.2 no
    C2 C3 H3 . . 107.2 no
    O1 C4 H4 . . 108.2 no
    C5 C4 H4 . . 108.2 no
    C3 C4 H4 . . 108.2 no
    C4 C5 H5A . . 109.5 no
    C4 C5 H5B . . 109.5 no
    H5A C5 H5B . . 109.5 no
    C4 C5 H5C . . 109.5 no
    H5A C5 H5C . . 109.5 no
    H5B C5 H5C . . 109.5 no
    C3 C6 H6A . . 109.5 no
    C3 C6 H6B . . 109.5 no
    H6A C6 H6B . . 109.5 no
    C3 C6 H6C . . 109.5 no
    H6A C6 H6C . . 109.5 no
    H6B C6 H6C . . 109.5 no
    C8 C9 H9A . . 109.6 no
    C10 C9 H9A . . 109.6 no
    C8 C9 H9B . . 109.6 no
    C10 C9 H9B . . 109.6 no
    H9A C9 H9B . . 108.1 no
    C9 C10 H10 . . 115.3 no
    C11 C10 H10 . . 115.3 no
    C13 C10 H10 . . 115.3 no
    C10 C11 H11A . . 114.3 no
    C12 C11 H11A . . 114.3 no
    C10 C11 H11B . . 114.3 no
    C12 C11 H11B . . 114.3 no
    H11A C11 H11B . . 111.4 no
    C7 C12 H12 . . 115.0 no
    C11 C12 H12 . . 115.0 no
    C13 C12 H12 . . 115.0 no
    C13 C14 H14A . . 109.5 no
    C13 C14 H14B . . 109.5 no
    H14A C14 H14B . . 109.5 no
    C13 C14 H14C . . 109.5 no
    H14A C14 H14C . . 109.5 no
    H14B C14 H14C . . 109.5 no
    C13 C15 H15A . . 109.5 no
    C13 C15 H15B . . 109.5 no
    H15A C15 H15B . . 109.5 no
    C13 C15 H15C . . 109.5 no
    H15A C15 H15C . . 109.5 no
    H15B C15 H15C . . 109.5 no
    C7 C16 H16A . . 109.5 no
    C7 C16 H16B . . 109.5 no
    H16A C16 H16B . . 109.5 no
    C7 C16 H16C . . 109.5 no
    H16A C16 H16C . . 109.5 no
    H16B C16 H16C . . 109.5 no
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C7 O3 C1 O2 . . . . 165.45(18) no
    C7 O3 C1 C2 . . . . -16.8(2) no
    C8 N1 C2 C1 . . . . 31.4(2) no
    C8 N1 C2 C3 . . . . 155.42(17) yes
    O2 C1 C2 N1 . . . . 154.7(2) no
    O3 C1 C2 N1 . . . . -22.8(2) no
    O2 C1 C2 C3 . . . . 31.8(3) no
    O3 C1 C2 C3 . . . . -145.74(17) yes
    N1 C2 C3 C6 . . . . -64.7(2) no
    C1 C2 C3 C6 . . . . 60.8(2) no
    N1 C2 C3 C4 . . . . 61.6(2) no
    C1 C2 C3 C4 . . . . -172.90(15) yes
    C6 C3 C4 O1 . . . . 55.3(2) no
    C2 C3 C4 O1 . . . . -70.2(2) yes
    C6 C3 C4 C5 . . . . -65.5(3) no
    C2 C3 C4 C5 . . . . 168.94(18) yes
    C1 O3 C7 C16 . . . . -77.0(2) no
    C1 O3 C7 C8 . . . . 44.9(2) no
    C1 O3 C7 C12 . . . . 160.32(16) no
    C2 N1 C8 C9 . . . . -172.59(17) no
    C2 N1 C8 C7 . . . .  .0(3) no
    O3 C7 C8 N1 . . . . -37.5(2) no
    C16 C7 C8 N1 . . . . 79.8(2) no
    C12 C7 C8 N1 . . . . -149.57(19) no
    O3 C7 C8 C9 . . . . 135.27(17) no
    C16 C7 C8 C9 . . . . -107.4(2) no
    C12 C7 C8 C9 . . . . 23.2(2) no
    N1 C8 C9 C10 . . . . 147.37(19) no
    C7 C8 C9 C10 . . . . -25.6(3) no
    C8 C9 C10 C11 . . . . -32.9(2) no
    C8 C9 C10 C13 . . . . 62.4(2) no
    C9 C10 C11 C12 . . . . 84.0(2) no
    C13 C10 C11 C12 . . . . -27.69(16) no
    O3 C7 C12 C11 . . . . -77.21(18) no
    C16 C7 C12 C11 . . . . 166.40(17) no
    C8 C7 C12 C11 . . . . 36.9(2) no
    O3 C7 C12 C13 . . . . -171.55(16) no
    C16 C7 C12 C13 . . . . 72.1(2) no
    C8 C7 C12 C13 . . . . -57.5(2) no
    C10 C11 C12 C7 . . . . -86.83(18) no
    C10 C11 C12 C13 . . . . 27.27(16) no
    C9 C10 C13 C15 . . . . 43.8(3) no
    C11 C10 C13 C15 . . . . 152.8(2) no
    C9 C10 C13 C14 . . . . 169.05(19) no
    C11 C10 C13 C14 . . . . -81.9(2) no
    C9 C10 C13 C12 . . . . -81.65(18) no
    C11 C10 C13 C12 . . . . 27.41(15) no
    C7 C12 C13 C15 . . . . -40.6(3) no
    C11 C12 C13 C15 . . . . -148.5(2) no
    C7 C12 C13 C14 . . . . -167.6(2) no
    C11 C12 C13 C14 . . . . 84.4(2) no
    C7 C12 C13 C10 . . . . 80.83(19) no
    C11 C12 C13 C10 . . . . -27.15(16) no
