##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
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     2010-01-27
_journal_date_accepted     2010-03-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      4
_journal_page_first     o902
_journal_page_last     o903
_journal_paper_category     QO
_journal_coeditor_code     ZL2269
_publ_contact_author_name     'Ferrence, Gregory M.'
_publ_contact_author_address
;
CB 4160
Department of Chemistry
Illinois State University
Normal, IL 61790
;
_publ_contact_author_email     ferrence@illinoisstate.edu
_publ_contact_author_fax     '(309)4385538'
_publ_contact_author_phone     '(309)4387971'
_publ_section_title
;\
(6S)-2-tert-Butyl-6-[(4S/i>,5R)-3,4-dimethyl-\
5-phenyloxazolidin-2-yl]phenol
;
loop_
    _publ_author_name
    _publ_author_address
    'Alexander E. Anderson'
;
CB 4160
Department of Chemistry
Illinois State University
Normal, IL 61790, USA
;
    'Kate L. Edler'
;
CB 4160
Department of Chemistry
Illinois State University
Normal, IL 61790, USA
;
    'Raleigh W. Parrott II'
;
CB 4160
Department of Chemistry
Illinois State University
Normal, IL 61790, USA
;
    'Shawn R. Hitchcock'
;
CB 4160
Department of Chemistry
Illinois State University
Normal, IL 61790, USA
;
    'Gregory M. Ferrence'
;
CB 4160
Department of Chemistry
Illinois State University
Normal, IL 61790, USA
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_name_systematic
;
(6S)-2-tert-Butyl-6-[(4S/i>,5R)-3,4-dimethyl-
5-phenyloxazolidin-2-yl]phenol
;
_chemical_formula_moiety     'C21 H27 N1 O2'
_chemical_formula_sum     'C21 H27 N1 O2'
_chemical_formula_iupac     'C21 H27 N1 O2'
_chemical_formula_weight     325.44
_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     8.3288(8)
_cell_length_b     9.8657(9)
_cell_length_c     11.4325(11)
_cell_angle_alpha     90
_cell_angle_beta     91.6670(10)
_cell_angle_gamma     90
_cell_volume     939.00(15)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5731
_cell_measurement_theta_min     2.4465
_cell_measurement_theta_max     3.354
_cell_measurement_temperature     140(2)
_exptl_crystal_description     rod
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.55
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.27
_exptl_crystal_density_diffrn     1.151
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     352
_exptl_absorpt_coefficient_mu     0.073
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(APEX2; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.6868
_exptl_absorpt_correction_T_max     0.7462
_diffrn_ambient_temperature     140(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9040
_diffrn_reflns_av_R_equivalents     0.0171
_diffrn_reflns_theta_min     1.78
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     1
_diffrn_measured_fraction_theta_full     1
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_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 >
2σ(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     2284
_reflns_number_gt     2191
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0293
_refine_ls_R_factor_gt     0.0275
_refine_ls_wR_factor_ref     0.0743
_refine_ls_goodness_of_fit_ref     1.04
_refine_ls_restrained_S_all     1.04
_refine_ls_number_reflns     2284
_refine_ls_number_parameters     221
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0485P)²+0.0900P] 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
_refine_ls_shift/su_mean     0
_refine_diff_density_max     0.213
_refine_diff_density_min     -0.142
_refine_ls_extinction_method     none
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 0 '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'
    O O 0.0106 0.006 '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     'SIR2004 (Burla et al.,  2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
WinGX (Farrugia, 1999), publCIF (McMahon & Westrip,
2008) and
Mercury (Macrae et al., 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 0.99692(12) 0.27815(11) 0.41600(9) 0.0248(2) Uani d . 1 . .
    O O20 0.65433(12) 0.17836(11) 0.28853(9) 0.0213(2) Uani d . 1 . .
    N N3 0.79655(14) 0.40974(12) 0.33736(10) 0.0202(2) Uani d . 1 . .
    C C16 0.75996(15) 0.03243(13) 0.14241(11) 0.0174(3) Uani d . 1 . .
    C C14 0.91785(16) 0.22492(14) 0.21866(11) 0.0185(3) Uani d . 1 . .
    C C19 1.04036(16) 0.19395(15) 0.14295(12) 0.0204(3) Uani d . 1 . .
    H H19 1.1354 0.2472 0.1438 0.025 Uiso calc R 1 . .
    C C2 0.94417(16) 0.33629(15) 0.30751(12) 0.0210(3) Uani d . 1 . .
    H H2 1.0265 0.4016 0.2795 0.025 Uiso calc R 1 . .
    C C6 0.87041(16) 0.27789(16) 0.60254(12) 0.0233(3) Uani d . 1 . .
    C C15 0.77689(15) 0.14637(14) 0.21694(11) 0.0177(3) Uani d . 1 . .
    C C4 0.84147(17) 0.47509(15) 0.45020(13) 0.0241(3) Uani d . 1 . .
    H H4 0.9104 0.5556 0.4342 0.029 Uiso calc R 1 . .
    C C21 0.61341(16) -0.06087(14) 0.14940(12) 0.0189(3) Uani d . 1 . .
    C C23 0.60832(17) -0.12120(14) 0.27378(12) 0.0221(3) Uani d . 1 . .
    H H23A 0.515 -0.1811 0.2791 0.033 Uiso calc R 1 . .
    H H23B 0.6 -0.0477 0.3309 0.033 Uiso calc R 1 . .
    H H23C 0.7067 -0.1731 0.2903 0.033 Uiso calc R 1 . .
    C C8 0.71138(18) 0.08617(17) 0.66066(14) 0.0280(3) Uani d . 1 . .
    H H8 0.6469 0.0099 0.6402 0.034 Uiso calc R 1 . .
    C C22 0.62164(19) -0.17981(16) 0.06338(13) 0.0273(3) Uani d . 1 . .
    H H22A 0.526 -0.2368 0.0706 0.041 Uiso calc R 1 . .
    H H22B 0.718 -0.2338 0.0813 0.041 Uiso calc R 1 . .
    H H22C 0.6261 -0.1448 -0.0167 0.041 Uiso calc R 1 . .
    C C17 0.88590(16) 0.00653(14) 0.06749(11) 0.0199(3) Uani d . 1 . .
    H H17 0.8768 -0.0681 0.0152 0.024 Uiso calc R 1 . .
    C C13 0.7473(2) 0.50590(16) 0.24528(14) 0.0285(3) Uani d . 1 . .
    H H13A 0.6492 0.5527 0.2679 0.043 Uiso calc R 1 . .
    H H13B 0.7267 0.4568 0.1718 0.043 Uiso calc R 1 . .
    H H13C 0.833 0.5724 0.2345 0.043 Uiso calc R 1 . .
    C C9 0.74020(19) 0.11793(18) 0.77790(14) 0.0316(4) Uani d . 1 . .
    H H9 0.6968 0.0629 0.8374 0.038 Uiso calc R 1 . .
    C C5 0.94712(16) 0.36461(16) 0.51019(12) 0.0242(3) Uani d . 1 . .
    H H5 1.0446 0.4091 0.546 0.029 Uiso calc R 1 . .
    C C18 1.02423(16) 0.08575(15) 0.06636(12) 0.0215(3) Uani d . 1 . .
    H H18 1.1069 0.0657 0.0135 0.026 Uiso calc R 1 . .
    C C11 0.89769(18) 0.30989(18) 0.72035(13) 0.0284(3) Uani d . 1 . .
    H H11 0.9612 0.3866 0.7412 0.034 Uiso calc R 1 . .
    C C24 0.45695(17) 0.01669(16) 0.11992(14) 0.0257(3) Uani d . 1 . .
    H H24A 0.3653 -0.0452 0.1249 0.039 Uiso calc R 1 . .
    H H24B 0.4612 0.0534 0.0404 0.039 Uiso calc R 1 . .
    H H24C 0.4447 0.0912 0.1757 0.039 Uiso calc R 1 . .
    C C10 0.8326(2) 0.23041(19) 0.80740(14) 0.0323(4) Uani d . 1 . .
    H H10 0.8516 0.2532 0.8874 0.039 Uiso calc R 1 . .
    C C12 0.69710(19) 0.52203(17) 0.51714(14) 0.0301(3) Uani d . 1 . .
    H H12A 0.6389 0.5915 0.4717 0.045 Uiso calc R 1 . .
    H H12B 0.7333 0.5601 0.5926 0.045 Uiso calc R 1 . .
    H H12C 0.6259 0.4448 0.5304 0.045 Uiso calc R 1 . .
    C C7 0.77616(17) 0.16510(16) 0.57324(13) 0.0244(3) Uani d . 1 . .
    H H7 0.7564 0.1424 0.4934 0.029 Uiso calc R 1 . .
    H H20 0.680(2) 0.258(3) 0.3212(18) 0.040(5) Uiso d . 1 . .
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'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 . 1.4243(17) ?
    O1 C5 . 1.4441(17) ?
    O20 C15 . 1.3638(15) ?
    O20 H20 . 0.90(2) ?
    N3 C13 . 1.4667(19) ?
    N3 C2 . 1.4756(18) ?
    N3 C4 . 1.4805(18) ?
    C16 C17 . 1.3970(18) ?
    C16 C15 . 1.4151(18) ?
    C16 C21 . 1.5327(18) ?
    C14 C19 . 1.3911(18) ?
    C14 C15 . 1.4064(18) ?
    C14 C2 . 1.5081(19) ?
    C19 C18 . 1.385(2) ?
    C19 H19 . 0.95 ?
    C2 H2 . 1 ?
    C6 C11 . 1.396(2) ?
    C6 C7 . 1.397(2) ?
    C6 C5 . 1.515(2) ?
    C4 C12 . 1.516(2) ?
    C4 C5 . 1.548(2) ?
    C4 H4 . 1 ?
    C21 C22 . 1.5338(19) ?
    C21 C24 . 1.540(2) ?
    C21 C23 . 1.5433(18) ?
    C23 H23A . 0.98 ?
    C23 H23B . 0.98 ?
    C23 H23C . 0.98 ?
    C8 C7 . 1.388(2) ?
    C8 C9 . 1.391(2) ?
    C8 H8 . 0.95 ?
    C22 H22A . 0.98 ?
    C22 H22B . 0.98 ?
    C22 H22C . 0.98 ?
    C17 C18 . 1.393(2) ?
    C17 H17 . 0.95 ?
    C13 H13A . 0.98 ?
    C13 H13B . 0.98 ?
    C13 H13C . 0.98 ?
    C9 C10 . 1.387(3) ?
    C9 H9 . 0.95 ?
    C5 H5 . 1 ?
    C18 H18 . 0.95 ?
    C11 C10 . 1.389(2) ?
    C11 H11 . 0.95 ?
    C24 H24A . 0.98 ?
    C24 H24B . 0.98 ?
    C24 H24C . 0.98 ?
    C10 H10 . 0.95 ?
    C12 H12A . 0.98 ?
    C12 H12B . 0.98 ?
    C12 H12C . 0.98 ?
    C7 H7 . 0.95 ?
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 . . 108.87(11) ?
    C15 O20 H20 . . 106.2(13) ?
    C13 N3 C2 . . 111.67(11) ?
    C13 N3 C4 . . 113.71(12) ?
    C2 N3 C4 . . 102.96(11) ?
    C17 C16 C15 . . 116.81(12) ?
    C17 C16 C21 . . 122.37(12) ?
    C15 C16 C21 . . 120.75(11) ?
    C19 C14 C15 . . 119.83(12) ?
    C19 C14 C2 . . 118.96(12) ?
    C15 C14 C2 . . 121.05(11) ?
    C18 C19 C14 . . 120.22(13) ?
    C18 C19 H19 . . 119.9 ?
    C14 C19 H19 . . 119.9 ?
    O1 C2 N3 . . 103.56(10) ?
    O1 C2 C14 . . 109.16(12) ?
    N3 C2 C14 . . 114.06(11) ?
    O1 C2 H2 . . 110 ?
    N3 C2 H2 . . 110 ?
    C14 C2 H2 . . 110 ?
    C11 C6 C7 . . 119.09(14) ?
    C11 C6 C5 . . 119.00(14) ?
    C7 C6 C5 . . 121.90(13) ?
    O20 C15 C14 . . 120.21(12) ?
    O20 C15 C16 . . 118.81(12) ?
    C14 C15 C16 . . 120.97(11) ?
    N3 C4 C12 . . 112.88(12) ?
    N3 C4 C5 . . 101.85(11) ?
    C12 C4 C5 . . 116.12(13) ?
    N3 C4 H4 . . 108.5 ?
    C12 C4 H4 . . 108.5 ?
    C5 C4 H4 . . 108.5 ?
    C16 C21 C22 . . 112.05(11) ?
    C16 C21 C24 . . 111.12(11) ?
    C22 C21 C24 . . 107.05(12) ?
    C16 C21 C23 . . 108.84(11) ?
    C22 C21 C23 . . 107.38(12) ?
    C24 C21 C23 . . 110.34(11) ?
    C21 C23 H23A . . 109.5 ?
    C21 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C21 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C7 C8 C9 . . 120.51(16) ?
    C7 C8 H8 . . 119.7 ?
    C9 C8 H8 . . 119.7 ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C18 C17 C16 . . 122.63(13) ?
    C18 C17 H17 . . 118.7 ?
    C16 C17 H17 . . 118.7 ?
    N3 C13 H13A . . 109.5 ?
    N3 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    N3 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C10 C9 C8 . . 119.59(15) ?
    C10 C9 H9 . . 120.2 ?
    C8 C9 H9 . . 120.2 ?
    O1 C5 C6 . . 108.80(12) ?
    O1 C5 C4 . . 104.91(11) ?
    C6 C5 C4 . . 117.42(11) ?
    O1 C5 H5 . . 108.5 ?
    C6 C5 H5 . . 108.5 ?
    C4 C5 H5 . . 108.5 ?
    C19 C18 C17 . . 119.46(12) ?
    C19 C18 H18 . . 120.3 ?
    C17 C18 H18 . . 120.3 ?
    C10 C11 C6 . . 120.52(15) ?
    C10 C11 H11 . . 119.7 ?
    C6 C11 H11 . . 119.7 ?
    C21 C24 H24A . . 109.5 ?
    C21 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C21 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    C9 C10 C11 . . 120.18(15) ?
    C9 C10 H10 . . 119.9 ?
    C11 C10 H10 . . 119.9 ?
    C4 C12 H12A . . 109.5 ?
    C4 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C4 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C8 C7 C6 . . 120.11(14) ?
    C8 C7 H7 . . 119.9 ?
    C6 C7 H7 . . 119.9 ?
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
    C15 C14 C19 C18 . . . . -0.3(2) ?
    C2 C14 C19 C18 . . . . 175.24(12) ?
    C5 O1 C2 N3 . . . . -29.88(13) ?
    C5 O1 C2 C14 . . . . -151.74(11) ?
    C13 N3 C2 O1 . . . . 164.76(12) ?
    C4 N3 C2 O1 . . . . 42.40(13) ?
    C13 N3 C2 C14 . . . . -76.72(15) ?
    C4 N3 C2 C14 . . . . 160.91(11) ?
    C19 C14 C2 O1 . . . . -95.64(14) ?
    C15 C14 C2 O1 . . . . 79.84(15) ?
    C19 C14 C2 N3 . . . . 149.09(13) ?
    C15 C14 C2 N3 . . . . -35.44(17) ?
    C19 C14 C15 O20 . . . . -178.14(12) ?
    C2 C14 C15 O20 . . . . 6.42(19) ?
    C19 C14 C15 C16 . . . . 2.55(19) ?
    C2 C14 C15 C16 . . . . -172.88(13) ?
    C17 C16 C15 O20 . . . . 177.65(12) ?
    C21 C16 C15 O20 . . . . -5.34(18) ?
    C17 C16 C15 C14 . . . . -3.03(18) ?
    C21 C16 C15 C14 . . . . 173.98(12) ?
    C13 N3 C4 C12 . . . . 76.22(16) ?
    C2 N3 C4 C12 . . . . -162.80(12) ?
    C13 N3 C4 C5 . . . . -158.56(12) ?
    C2 N3 C4 C5 . . . . -37.58(13) ?
    C17 C16 C21 C22 . . . . -1.61(18) ?
    C15 C16 C21 C22 . . . . -178.45(12) ?
    C17 C16 C21 C24 . . . . -121.31(14) ?
    C15 C16 C21 C24 . . . . 61.85(16) ?
    C17 C16 C21 C23 . . . . 116.99(14) ?
    C15 C16 C21 C23 . . . . -59.85(16) ?
    C15 C16 C17 C18 . . . . 1.39(19) ?
    C21 C16 C17 C18 . . . . -175.57(12) ?
    C7 C8 C9 C10 . . . . 0.9(2) ?
    C2 O1 C5 C6 . . . . 132.44(12) ?
    C2 O1 C5 C4 . . . . 6.00(14) ?
    C11 C6 C5 O1 . . . . 142.27(13) ?
    C7 C6 C5 O1 . . . . -36.26(17) ?
    C11 C6 C5 C4 . . . . -98.86(15) ?
    C7 C6 C5 C4 . . . . 82.61(17) ?
    N3 C4 C5 O1 . . . . 19.92(13) ?
    C12 C4 C5 O1 . . . . 142.96(13) ?
    N3 C4 C5 C6 . . . . -101.00(13) ?
    C12 C4 C5 C6 . . . . 22.04(18) ?
    C14 C19 C18 C17 . . . . -1.3(2) ?
    C16 C17 C18 C19 . . . . 0.8(2) ?
    C7 C6 C11 C10 . . . . 0.3(2) ?
    C5 C6 C11 C10 . . . . -178.31(13) ?
    C8 C9 C10 C11 . . . . -0.8(2) ?
    C6 C11 C10 C9 . . . . 0.2(2) ?
    C9 C8 C7 C6 . . . . -0.4(2) ?
    C11 C6 C7 C8 . . . . -0.2(2) ?
    C5 C6 C7 C8 . . . . 178.33(13) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    O20 H20 N3 . 0.90(2) 1.79(2) 2.6244(16) 154.4(19)
