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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 2.4.    #
#                                                                            #
# 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/  #
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# This file may be used for bona fide research purposes within the           #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
[(2S,5R,6S,9R)-6-isopropyl-9-methyl-1,4-
dioxaspiro[4.5]dec-2-yl]methyl 3,5-dinitrobenzoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H26 N2 O8'
_chemical_formula_sum     'C20 H26 N2 O8'
_chemical_formula_iupac     'C20 H26 N2 O8'
_chemical_formula_weight     422.43
_chemical_melting_point     368
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     9.4396(5)
_cell_length_b     5.8825(3)
_cell_length_c     19.6719(10)
_cell_angle_alpha     90.00
_cell_angle_beta     103.923(3)
_cell_angle_gamma     90.00
_cell_volume     1060.26(9)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     9947
_cell_measurement_theta_min     2.31
_cell_measurement_theta_max     68.20
_cell_measurement_temperature     100(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.376
_exptl_crystal_size_mid     0.09
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.323
_exptl_crystal_density_meas     ?
_exptl_crystal_F_000     448
_exptl_absorpt_coefficient_mu     0.866
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.6024
_exptl_absorpt_correction_T_max     0.9770
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_reflns_number     16481
_diffrn_reflns_av_R_equivalents     0.0245
_diffrn_reflns_av_sigmaI/netI     0.0168
_diffrn_reflns_theta_min     2.31
_diffrn_reflns_theta_max     68.23
_diffrn_reflns_theta_full     68.23
_diffrn_measured_fraction_theta_max     0.970
_diffrn_measured_fraction_theta_full     0.969
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_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 >
σ(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. The structure was refined as a pseudo-merohedral twin (monoclinic
space group P2₁ emulating orthorhombic space group C222₁);
Twin law 1 0 0 0 - 1 0 - 1 0 - 1; Refined ratio (BASF) 0.3790(7).
Hydrogen positions were calculated and refined using a riding model using the
following C---H distances: methyne 1.000 Å, methylene 0.990 Å, methyl
0.980Å and aromatic 0.950 Å. The isotropic U values for the H atoms were
set at 50% above that of bonded carbon for methyl H atoms and 20% above that
of the bonded carbon for all other H atoms.
;
_reflns_number_total     3275
_reflns_number_gt     3254
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0183
_refine_ls_R_factor_gt     0.0181
_refine_ls_wR_factor_gt     0.0450
_refine_ls_wR_factor_ref     0.0452
_refine_ls_goodness_of_fit_ref     1.063
_refine_ls_restrained_S_all     1.063
_refine_ls_number_reflns     3275
_refine_ls_number_parameters     276
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0245P)²+0.0832P] 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     0.000
_refine_diff_density_max     0.100
_refine_diff_density_min     -0.109
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0009(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983), 1131 Friedel pairs'
_refine_ls_abs_structure_Flack     0.03(13)
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'
    'H' 'H' 0.0000 0.0000
                         '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'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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
    O O1 0.72662(12) -0.12929(19) 0.71101(5) 0.0258(3) Uani d . 1 . .
    C C2 0.81610(17) -0.1291(3) 0.78046(7) 0.0227(3) Uani d . 1 . .
    H H2 0.9171 -0.1783 0.7796 0.027 Uiso calc R 1 . .
    C C3 0.81810(17) 0.1200(3) 0.80073(8) 0.0222(3) Uani d . 1 . .
    H H3A 0.7329 0.1589 0.8196 0.027 Uiso calc R 1 . .
    H H3B 0.9088 0.1591 0.8359 0.027 Uiso calc R 1 . .
    O O4 0.81137(12) 0.23300(19) 0.73591(5) 0.0227(2) Uani d . 1 . .
    C C5 0.72348(19) 0.0946(3) 0.68212(8) 0.0232(3) Uani d . 1 . .
    C C6 0.78923(18) 0.0943(3) 0.61799(8) 0.0266(4) Uani d . 1 . .
    H H6 0.7245 -0.0053 0.5824 0.032 Uiso calc R 1 . .
    C C7 0.7763(2) 0.3330(3) 0.58613(8) 0.0329(4) Uani d . 1 . .
    H H7A 0.8359 0.4400 0.6202 0.039 Uiso calc R 1 . .
    H H7B 0.8154 0.3319 0.5437 0.039 Uiso calc R 1 . .
    C C8 0.6194(2) 0.4149(4) 0.56676(8) 0.0365(4) Uani d . 1 . .
    H H8A 0.5619 0.3166 0.5293 0.044 Uiso calc R 1 . .
    H H8B 0.6163 0.5717 0.5482 0.044 Uiso calc R 1 . .
    C C9 0.54978(19) 0.4117(3) 0.62943(8) 0.0308(4) Uani d . 1 . .
    H H9 0.6041 0.5223 0.6649 0.037 Uiso calc R 1 . .
    C C10 0.56642(18) 0.1768(3) 0.66303(8) 0.0270(4) Uani d . 1 . .
    H H10A 0.5289 0.1811 0.7059 0.032 Uiso calc R 1 . .
    H H10B 0.5063 0.0670 0.6302 0.032 Uiso calc R 1 . .
    C C11 0.3900(2) 0.4850(4) 0.60923(11) 0.0461(5) Uani d . 1 . .
    H H11A 0.3347 0.3813 0.5736 0.069 Uiso calc R 1 . .
    H H11B 0.3831 0.6400 0.5904 0.069 Uiso calc R 1 . .
    H H11C 0.3497 0.4809 0.6507 0.069 Uiso calc R 1 . .
    C C12 0.9428(2) -0.0117(4) 0.63175(9) 0.0344(4) Uani d . 1 . .
    H H12 0.9459 -0.1414 0.6649 0.041 Uiso calc R 1 . .
    C C13 0.9717(2) -0.1084(4) 0.56378(9) 0.0400(5) Uani d . 1 . .
    H H13A 0.9693 0.0152 0.5301 0.060 Uiso calc R 1 . .
    H H13B 0.8964 -0.2206 0.5439 0.060 Uiso calc R 1 . .
    H H13C 1.0678 -0.1814 0.5740 0.060 Uiso calc R 1 . .
    C C14 1.0663(2) 0.1510(5) 0.66460(13) 0.0633(8) Uani d . 1 . .
    H H14A 1.1582 0.0664 0.6782 0.095 Uiso calc R 1 . .
    H H14B 1.0452 0.2222 0.7061 0.095 Uiso calc R 1 . .
    H H14C 1.0748 0.2687 0.6306 0.095 Uiso calc R 1 . .
    C C15 0.75391(17) -0.2914(3) 0.82456(8) 0.0241(3) Uani d . 1 . .
    H H15A 0.7341 -0.4403 0.8007 0.029 Uiso calc R 1 . .
    H H15B 0.8241 -0.3148 0.8703 0.029 Uiso calc R 1 . .
    O O16 0.61928(12) -0.19409(19) 0.83493(5) 0.0219(3) Uani d . 1 . .
    C C17 0.55649(16) -0.3039(3) 0.87874(7) 0.0204(3) Uani d . 1 . .
    C C18 0.43170(16) -0.1728(3) 0.89389(7) 0.0195(3) Uani d . 1 . .
    C C19 0.36462(15) -0.2611(3) 0.94374(7) 0.0207(3) Uani d . 1 . .
    H H19 0.3984 -0.3989 0.9673 0.025 Uiso calc R 1 . .
    C C20 0.24814(16) -0.1456(3) 0.95844(7) 0.0196(3) Uani d . 1 . .
    C C21 0.19642(16) 0.0567(3) 0.92634(7) 0.0197(3) Uani d . 1 . .
    H H21 0.1167 0.1350 0.9373 0.024 Uiso calc R 1 . .
    C C22 0.26696(16) 0.1397(3) 0.87730(8) 0.0203(3) Uani d . 1 . .
    C C23 0.38314(16) 0.0311(3) 0.86020(8) 0.0196(3) Uani d . 1 . .
    H H23 0.4288 0.0936 0.8264 0.024 Uiso calc R 1 . .
    O O24 0.59532(12) -0.4860(2) 0.90476(6) 0.0267(3) Uani d . 1 . .
    N N25 0.21586(14) 0.3563(2) 0.84164(6) 0.0219(3) Uani d . 1 . .
    O O26 0.28039(12) 0.4291(2) 0.79908(5) 0.0270(3) Uani d . 1 . .
    O O27 0.11232(11) 0.4517(2) 0.85721(6) 0.0275(3) Uani d . 1 . .
    N N28 0.17654(13) -0.2454(3) 1.01017(6) 0.0222(3) Uani d . 1 . .
    O O29 0.07569(12) -0.1400(2) 1.02463(6) 0.0299(3) Uani d . 1 . .
    O O30 0.22049(12) -0.4300(2) 1.03556(6) 0.0271(3) Uani d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    O1 C2 . 1.4230(17) ?
    O1 C5 . 1.432(2) ?
    C2 C15 . 1.501(2) ?
    C2 C3 . 1.518(2) ?
    C2 H2 . 1.0000 ?
    C3 O4 . 1.4259(18) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    O4 C5 . 1.4310(19) ?
    C5 C10 . 1.518(2) ?
    C5 C6 . 1.534(2) ?
    C6 C7 . 1.531(3) ?
    C6 C12 . 1.541(2) ?
    C6 H6 . 1.0000 ?
    C7 C8 . 1.517(3) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 C9 . 1.530(2) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 C10 . 1.523(3) ?
    C9 C11 . 1.526(3) ?
    C9 H9 . 1.0000 ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 C14 . 1.526(3) ?
    C12 C13 . 1.537(2) ?
    C12 H12 . 1.0000 ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C14 H14C . 0.9800 ?
    C15 O16 . 1.4523(18) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    O16 C17 . 1.3257(19) ?
    C17 O24 . 1.206(2) ?
    C17 C18 . 1.497(2) ?
    C18 C19 . 1.390(2) ?
    C18 C23 . 1.393(2) ?
    C19 C20 . 1.381(2) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.380(2) ?
    C20 N28 . 1.4726(19) ?
    C21 C22 . 1.386(2) ?
    C21 H21 . 0.9500 ?
    C22 C23 . 1.379(2) ?
    C22 N25 . 1.478(2) ?
    C23 H23 . 0.9500 ?
    N25 O26 . 1.2253(17) ?
    N25 O27 . 1.2280(17) ?
    N28 O30 . 1.2254(18) ?
    N28 O29 . 1.2256(18) ?
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
    C2 O1 C5 . . 109.35(12) ?
    O1 C2 C15 . . 109.28(13) ?
    O1 C2 C3 . . 102.70(13) ?
    C15 C2 C3 . . 116.37(13) ?
    O1 C2 H2 . . 109.4 ?
    C15 C2 H2 . . 109.4 ?
    C3 C2 H2 . . 109.4 ?
    O4 C3 C2 . . 102.72(12) ?
    O4 C3 H3A . . 111.2 ?
    C2 C3 H3A . . 111.2 ?
    O4 C3 H3B . . 111.2 ?
    C2 C3 H3B . . 111.2 ?
    H3A C3 H3B . . 109.1 ?
    C3 O4 C5 . . 106.81(11) ?
    O4 C5 O1 . . 106.07(11) ?
    O4 C5 C10 . . 111.08(13) ?
    O1 C5 C10 . . 108.47(14) ?
    O4 C5 C6 . . 109.35(13) ?
    O1 C5 C6 . . 110.57(14) ?
    C10 C5 C6 . . 111.17(13) ?
    C7 C6 C5 . . 109.12(14) ?
    C7 C6 C12 . . 114.98(15) ?
    C5 C6 C12 . . 113.93(14) ?
    C7 C6 H6 . . 106.0 ?
    C5 C6 H6 . . 106.0 ?
    C12 C6 H6 . . 106.0 ?
    C8 C7 C6 . . 111.77(15) ?
    C8 C7 H7A . . 109.3 ?
    C6 C7 H7A . . 109.3 ?
    C8 C7 H7B . . 109.3 ?
    C6 C7 H7B . . 109.3 ?
    H7A C7 H7B . . 107.9 ?
    C7 C8 C9 . . 112.11(14) ?
    C7 C8 H8A . . 109.2 ?
    C9 C8 H8A . . 109.2 ?
    C7 C8 H8B . . 109.2 ?
    C9 C8 H8B . . 109.2 ?
    H8A C8 H8B . . 107.9 ?
    C10 C9 C11 . . 111.20(15) ?
    C10 C9 C8 . . 109.96(15) ?
    C11 C9 C8 . . 112.06(15) ?
    C10 C9 H9 . . 107.8 ?
    C11 C9 H9 . . 107.8 ?
    C8 C9 H9 . . 107.8 ?
    C5 C10 C9 . . 112.88(14) ?
    C5 C10 H10A . . 109.0 ?
    C9 C10 H10A . . 109.0 ?
    C5 C10 H10B . . 109.0 ?
    C9 C10 H10B . . 109.0 ?
    H10A C10 H10B . . 107.8 ?
    C9 C11 H11A . . 109.5 ?
    C9 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C9 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C14 C12 C13 . . 108.84(16) ?
    C14 C12 C6 . . 114.26(18) ?
    C13 C12 C6 . . 110.70(15) ?
    C14 C12 H12 . . 107.6 ?
    C13 C12 H12 . . 107.6 ?
    C6 C12 H12 . . 107.6 ?
    C12 C13 H13A . . 109.5 ?
    C12 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C12 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C12 C14 H14A . . 109.5 ?
    C12 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C12 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    O16 C15 C2 . . 107.91(13) ?
    O16 C15 H15A . . 110.1 ?
    C2 C15 H15A . . 110.1 ?
    O16 C15 H15B . . 110.1 ?
    C2 C15 H15B . . 110.1 ?
    H15A C15 H15B . . 108.4 ?
    C17 O16 C15 . . 116.25(13) ?
    O24 C17 O16 . . 124.84(15) ?
    O24 C17 C18 . . 123.15(14) ?
    O16 C17 C18 . . 112.00(14) ?
    C19 C18 C23 . . 120.27(14) ?
    C19 C18 C17 . . 117.49(15) ?
    C23 C18 C17 . . 122.24(13) ?
    C20 C19 C18 . . 118.97(15) ?
    C20 C19 H19 . . 120.5 ?
    C18 C19 H19 . . 120.5 ?
    C21 C20 C19 . . 122.72(14) ?
    C21 C20 N28 . . 119.29(14) ?
    C19 C20 N28 . . 117.99(15) ?
    C20 C21 C22 . . 116.46(14) ?
    C20 C21 H21 . . 121.8 ?
    C22 C21 H21 . . 121.8 ?
    C23 C22 C21 . . 123.38(15) ?
    C23 C22 N25 . . 118.12(13) ?
    C21 C22 N25 . . 118.50(13) ?
    C22 C23 C18 . . 118.20(14) ?
    C22 C23 H23 . . 120.9 ?
    C18 C23 H23 . . 120.9 ?
    O26 N25 O27 . . 124.54(14) ?
    O26 N25 C22 . . 117.82(13) ?
    O27 N25 C22 . . 117.64(12) ?
    O30 N28 O29 . . 124.03(13) ?
    O30 N28 C20 . . 117.93(13) ?
    O29 N28 C20 . . 118.03(14) ?
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
    C5 O1 C2 C15 . . . . 145.19(13) ?
    C5 O1 C2 C3 . . . . 21.05(15) ?
    O1 C2 C3 O4 . . . . -33.31(15) ?
    C15 C2 C3 O4 . . . . -152.61(12) ?
    C2 C3 O4 C5 . . . . 33.85(16) ?
    C3 O4 C5 O1 . . . . -21.48(16) ?
    C3 O4 C5 C10 . . . . 96.20(14) ?
    C3 O4 C5 C6 . . . . -140.74(14) ?
    C2 O1 C5 O4 . . . . -0.87(16) ?
    C2 O1 C5 C10 . . . . -120.27(13) ?
    C2 O1 C5 C6 . . . . 117.59(14) ?
    O4 C5 C6 C7 . . . . -66.69(17) ?
    O1 C5 C6 C7 . . . . 176.87(13) ?
    C10 C5 C6 C7 . . . . 56.32(18) ?
    O4 C5 C6 C12 . . . . 63.30(19) ?
    O1 C5 C6 C12 . . . . -53.14(19) ?
    C10 C5 C6 C12 . . . . -173.69(15) ?
    C5 C6 C7 C8 . . . . -56.89(18) ?
    C12 C6 C7 C8 . . . . 173.69(14) ?
    C6 C7 C8 C9 . . . . 56.6(2) ?
    C7 C8 C9 C10 . . . . -53.50(19) ?
    C7 C8 C9 C11 . . . . -177.71(18) ?
    O4 C5 C10 C9 . . . . 65.68(16) ?
    O1 C5 C10 C9 . . . . -178.11(12) ?
    C6 C5 C10 C9 . . . . -56.33(18) ?
    C11 C9 C10 C5 . . . . 178.43(15) ?
    C8 C9 C10 C5 . . . . 53.72(17) ?
    C7 C6 C12 C14 . . . . 43.7(2) ?
    C5 C6 C12 C14 . . . . -83.3(2) ?
    C7 C6 C12 C13 . . . . -79.62(19) ?
    C5 C6 C12 C13 . . . . 153.37(16) ?
    O1 C2 C15 O16 . . . . -70.24(16) ?
    C3 C2 C15 O16 . . . . 45.44(18) ?
    C2 C15 O16 C17 . . . . -173.43(12) ?
    C15 O16 C17 O24 . . . . -7.2(2) ?
    C15 O16 C17 C18 . . . . 171.59(12) ?
    O24 C17 C18 C19 . . . . 4.1(2) ?
    O16 C17 C18 C19 . . . . -174.70(13) ?
    O24 C17 C18 C23 . . . . -176.18(15) ?
    O16 C17 C18 C23 . . . . 5.01(19) ?
    C23 C18 C19 C20 . . . . 1.0(2) ?
    C17 C18 C19 C20 . . . . -179.32(13) ?
    C18 C19 C20 C21 . . . . -1.0(2) ?
    C18 C19 C20 N28 . . . . 178.53(13) ?
    C19 C20 C21 C22 . . . . 0.6(2) ?
    N28 C20 C21 C22 . . . . -178.93(13) ?
    C20 C21 C22 C23 . . . . -0.1(2) ?
    C20 C21 C22 N25 . . . . -179.81(12) ?
    C21 C22 C23 C18 . . . . 0.2(2) ?
    N25 C22 C23 C18 . . . . 179.83(13) ?
    C19 C18 C23 C22 . . . . -0.6(2) ?
    C17 C18 C23 C22 . . . . 179.73(14) ?
    C23 C22 N25 O26 . . . . -0.60(19) ?
    C21 C22 N25 O26 . . . . 179.08(14) ?
    C23 C22 N25 O27 . . . . 179.99(13) ?
    C21 C22 N25 O27 . . . . -0.33(19) ?
    C21 C20 N28 O30 . . . . 176.82(13) ?
    C19 C20 N28 O30 . . . . -2.68(19) ?
    C21 C20 N28 O29 . . . . -2.41(19) ?
    C19 C20 N28 O29 . . . . 178.08(13) ?
data_global
_journal_date_recd_electronic     2009-05-19
_journal_date_accepted     2009-06-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      7
_journal_page_first     o1540
_journal_page_last     o1540
_journal_paper_category     QO
_journal_coeditor_code     ZL2211
_publ_contact_author_name     'Anthony Kiessling'
_publ_contact_author_address
;
Department of Chemistry and Physics
Mansfield University
Mansfield, PA 16933
;
_publ_contact_author_email     'akiessli@mansfield.edu'
_publ_contact_author_fax     '570-662-4107'
_publ_contact_author_phone     '570-662-4546'
_publ_section_title
;
3,5-Dinitrobenzoyl derivative of a stereoisomer of glycerol menthonide
;
loop_
    _publ_author_name
    _publ_author_address
    'Kiessling, Anthony'
;
Department of Chemistry and Physics
Mansfield University
Mansfield, PA 16933
USA
;
    'Campana, Charles'
;
Senior Scientist
Single CrystalDiffraction
Bruker AXS Inc.
5465 East Cheryl Parkway
Madison, WI 53711-5373
USA
;
    'Margaret E. Kastner'
;
Department of Chemistry
Bucknell University
Lewisburg, PA 17837
USA
;
