##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# 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     'SHELXL-2013'
_journal_date_recd_electronic     2013-09-11
_journal_date_accepted     2013-10-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue     11
_journal_page_first     o1709
_journal_page_last     o1710
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813028730
_journal_coeditor_code     SU2647
_publ_contact_author_name     'Dr P.A. Crooks'
_publ_contact_author_address
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Arkansas for Medical Sciences
Little Rock, AR 72205
USA
;
_publ_contact_author_email     'pacrooks@uams.edu'
_publ_contact_author_fax     '501 686 6057'
_publ_contact_author_phone     '501 686 6495'
_publ_section_title
;
(<i>E</i>)-13-(4-Aminophenyl)parthenolide
;
loop_
    _publ_author_name
    _publ_author_address
    'Narsimha Reddy Penthala'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Arkansas for Medical Sciences
Little Rock, AR 72205
USA
;
    'Venumadhav Janganati'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Arkansas for Medical Sciences
Little Rock, AR 72205
USA
;
    'Parkin, Sean'
;
Department of Chemistry
University of Kentucky
Lexington
KY 40506
USA
;
    'Varughese, Kottayil I. '
;
College of Medicine
Department of Physiology & Biophysics
University of Arkansas for Medical Sciences
Little Rock, AR 72205
USA
;
    'Crooks, Peter A.'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Arkansas for Medical Sciences
Little Rock, AR 72205
USA
;
data_I
_audit_creation_method     SHELXL-2013
_database_code_depnum_ccdc_archive     'CCDC 967357'
_chemical_name_systematic
;\
(3a<i>S</i>,9a<i>R</i>,10a<i>R</i>,10b<i>S</i>,<i>E</i>)-3-[(<i>E</i>)-4-\
(4-Aminobenzylidene)-6,9a-dimethyl-3a,4,5,8,9,9a,10a,10b-\
octahydrooxireno[2',3':9,10]cyclodeca[1,2-<i>b</i>]furan-2(3<i>H</i>)-one
;
_chemical_name_common
;
(<i>E</i>)-13-(4-Aminophenyl)parthenolide
;
_chemical_formula_moiety     'C21 H25 N O3'
_chemical_formula_sum     'C21 H25 N O3'
_chemical_formula_iupac     'C21 H25 N O3'
_chemical_formula_weight     339.42
_chemical_melting_point_gt     512
_chemical_melting_point_lt     514
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
    _space_group_symop_operation_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     8.56190(10)
_cell_length_b     11.8846(2)
_cell_length_c     17.7457(3)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1805.71(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9832
_cell_measurement_theta_min     5.17
_cell_measurement_theta_max     67.98
_cell_measurement_temperature     90.0(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.249
_exptl_crystal_density_meas     .
_exptl_crystal_density_method     .
_exptl_crystal_F_000     728
_exptl_absorpt_coefficient_mu     0.662
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Sheldrick, 1996)
;
_shelx_estimated_absorpt_T_min     0.879
_shelx_estimated_absorpt_T_max     0.925
_exptl_absorpt_correction_T_min     0.843
_exptl_absorpt_correction_T_max     0.956
_exptl_special_details
;
Spectroscopic data for the title compound: ^1^H NMR (400 MHz, CDCl~3~): \d
7.54-7.55 (d, <i>J</i>=2.8 Hz, 1H), 7.23-7.26 (d, <i>J</i>=8.4 Hz, 2H),
6.68-6.70 (d, <i>J</i>=8.0 Hz, 2H), 5.28-5.30 (d, <i>J</i>=11.2 Hz, 1H), 4.02
(brs, 2H), 3.91-3.95 (t, <i>J</i>=8.0Hz, 1H), 3.25 (m, 1H), 2.82-2.84 (d,
<i>J</i>=8.8 Hz, 1H), 2.28-2.45 (m, 1H), 2.14-2.24 (m, 5H), 1.69 (s, 3H), 1.61
(s, 1H), 1.43-1.45 (m, 1H), 1.31(s, 3H); ^13^C NMR (100 MHz,CDCl~3~) \d
171.63, 148.15, 138.64, 134.79, 132.17, 125.12, 124.03, 123.29, 114.42, 82.71,
66.62, 61.58, 46.98, 41.88, 36.10, 29.33, 24.33, 17.49, 17.36 <i>ppm</i>.
;
_diffrn_ambient_temperature     90.0(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_device_type     'Bruker X8 Proteum'
_diffrn_measurement_method     '\f and \w scans'
_diffrn_detector_area_resol_mean     5.6
_diffrn_reflns_number     25400
_diffrn_reflns_av_R_equivalents     0.0330
_diffrn_reflns_theta_min     5.737
_diffrn_reflns_theta_max     68.225
_diffrn_reflns_theta_full     67.679
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     15
_refine_special_details
;
;
_reflns_number_total     3296
_reflns_number_gt     3267
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0268
_refine_ls_R_factor_gt     0.0265
_refine_ls_wR_factor_gt     0.0699
_refine_ls_wR_factor_ref     0.0704
_refine_ls_goodness_of_fit_ref     1.062
_refine_ls_restrained_S_all     1.062
_refine_ls_number_reflns     3296
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+0.3030P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.126
_refine_diff_density_min     -0.135
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack parameter determined using 1383 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>, 2013)
;
_refine_ls_abs_structure_Flack     0.03(3)
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     '<i>APEX2</i> (Bruker, 2006)'
_computing_cell_refinement     '<i>SAINT</i> (Bruker, 2006)'
_computing_data_reduction     '<i>SAINT</i> (Bruker, 2006)'
_computing_structure_solution
;
<i>SHELXS97</i> (Sheldrick, 2008)
;
_computing_structure_refinement
;
<i>SHELXL2013</i> (Sheldrick, 2008)
;
_computing_molecular_graphics
;
<i>SHELXTL</i> (Sheldrick, 2008)
;
_computing_publication_material
;
<i>SHELXTL</i> (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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.69671(14) 0.83851(9) 0.57032(6) 0.0269(3) Uani d 1 . .
    O O2 0.57735(14) 0.71820(9) 0.43765(6) 0.0247(3) Uani d 1 . .
    O O3 0.57901(15) 0.65318(10) 0.31945(6) 0.0276(3) Uani d 1 . .
    N N1 0.48608(19) -0.03270(12) 0.45455(10) 0.0323(3) Uani d 1 . .
    H H1A 0.539(3) -0.055(2) 0.4989(14) 0.049 Uiso d 1 . .
    H H2B 0.495(3) -0.077(2) 0.4135(14) 0.049 Uiso d 1 . .
    C C1 0.61245(19) 0.79003(14) 0.63430(9) 0.0255(4) Uani d 1 . .
    C C2 0.7040(2) 0.76874(16) 0.70559(9) 0.0321(4) Uani d 1 . .
    H H1 0.7143 0.8397 0.7344 0.038 Uiso calc 1 . .
    H H2A 0.8102 0.7420 0.6926 0.038 Uiso calc 1 . .
    C C3 0.6202(2) 0.67944(15) 0.75440(9) 0.0325(4) Uani d 1 . .
    H H3A 0.6881 0.6579 0.7972 0.039 Uiso calc 1 . .
    H H3B 0.5227 0.7117 0.7752 0.039 Uiso calc 1 . .
    C C4 0.5821(2) 0.57669(14) 0.70835(9) 0.0277(4) Uani d 1 . .
    H H4 0.6688 0.5325 0.6928 0.033 Uiso calc 1 . .
    C C5 0.4420(2) 0.53993(13) 0.68657(8) 0.0248(3) Uani d 1 . .
    C C6 0.4284(2) 0.44729(13) 0.62863(8) 0.0259(3) Uani d 1 . .
    H H6A 0.3432 0.3957 0.6438 0.031 Uiso calc 1 . .
    H H6B 0.5268 0.4035 0.6282 0.031 Uiso calc 1 . .
    C C7 0.39551(19) 0.49041(13) 0.54839(8) 0.0237(3) Uani d 1 . .
    H H7A 0.3090 0.5455 0.5508 0.028 Uiso calc 1 . .
    H H7B 0.3597 0.4263 0.5172 0.028 Uiso calc 1 . .
    C C8 0.53600(18) 0.54638(12) 0.50866(8) 0.0198(3) Uani d 1 . .
    H H8 0.6346 0.5178 0.5321 0.024 Uiso calc 1 . .
    C C9 0.53593(18) 0.67758(12) 0.51252(8) 0.0209(3) Uani d 1 . .
    H H9 0.4293 0.7050 0.5263 0.025 Uiso calc 1 . .
    C C10 0.65311(18) 0.72056(12) 0.56849(8) 0.0219(3) Uani d 1 . .
    H H10 0.7423 0.6679 0.5775 0.026 Uiso calc 1 . .
    C C11 0.56586(19) 0.63346(13) 0.38588(8) 0.0225(3) Uani d 1 . .
    C C12 0.54277(18) 0.52539(12) 0.42479(8) 0.0207(3) Uani d 1 . .
    C C13 0.53493(19) 0.43138(13) 0.38311(8) 0.0223(3) Uani d 1 . .
    H H13 0.5363 0.4441 0.3303 0.027 Uiso calc 1 . .
    C C14 0.2884(2) 0.58698(15) 0.71301(10) 0.0321(4) Uani d 1 . .
    H H14A 0.3071 0.6429 0.7526 0.048 Uiso calc 1 . .
    H H14B 0.2236 0.5260 0.7331 0.048 Uiso calc 1 . .
    H H14C 0.2345 0.6227 0.6706 0.048 Uiso calc 1 . .
    C C15 0.4537(2) 0.84179(14) 0.64419(9) 0.0301(4) Uani d 1 . .
    H H15A 0.4639 0.9142 0.6702 0.045 Uiso calc 1 . .
    H H15B 0.3878 0.7913 0.6741 0.045 Uiso calc 1 . .
    H H15C 0.4057 0.8537 0.5947 0.045 Uiso calc 1 . .
    C C16 0.52461(18) 0.31328(13) 0.40450(9) 0.0228(3) Uani d 1 . .
    C C17 0.5641(2) 0.27104(12) 0.47583(8) 0.0253(3) Uani d 1 . .
    H H17 0.6003 0.3214 0.5136 0.030 Uiso calc 1 . .
    C C18 0.5517(2) 0.15768(13) 0.49238(9) 0.0276(3) Uani d 1 . .
    H H18 0.5777 0.1314 0.5414 0.033 Uiso calc 1 . .
    C C19 0.50076(19) 0.08115(13) 0.43735(10) 0.0266(3) Uani d 1 . .
    C C20 0.46429(19) 0.12208(14) 0.36578(9) 0.0266(3) Uani d 1 . .
    H H20 0.4306 0.0715 0.3276 0.032 Uiso calc 1 . .
    C C21 0.47670(19) 0.23526(13) 0.35002(9) 0.0245(3) Uani d 1 . .
    H H21 0.4521 0.2611 0.3008 0.029 Uiso calc 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0341(6) 0.0208(5) 0.0258(6) -0.0064(5) 0.0045(5) -0.0028(5)
    O2 0.0368(6) 0.0174(5) 0.0199(5) -0.0020(5) 0.0000(5) 0.0017(4)
    O3 0.0358(6) 0.0279(6) 0.0190(5) -0.0027(5) -0.0006(5) 0.0043(4)
    N1 0.0364(8) 0.0191(7) 0.0415(8) -0.0011(6) 0.0020(7) 0.0013(6)
    C1 0.0310(8) 0.0222(7) 0.0232(8) -0.0057(6) 0.0029(6) -0.0029(6)
    C2 0.0339(9) 0.0375(9) 0.0248(8) -0.0065(8) -0.0004(7) -0.0055(7)
    C3 0.0343(9) 0.0430(10) 0.0201(8) -0.0023(8) -0.0030(7) 0.0005(7)
    C4 0.0320(8) 0.0297(8) 0.0212(7) 0.0066(7) 0.0028(7) 0.0048(6)
    C5 0.0342(9) 0.0220(7) 0.0183(7) 0.0041(7) 0.0033(7) 0.0048(6)
    C6 0.0346(9) 0.0194(7) 0.0236(7) 0.0020(7) 0.0069(7) 0.0046(6)
    C7 0.0269(8) 0.0203(7) 0.0238(8) -0.0003(6) 0.0024(6) 0.0014(6)
    C8 0.0237(8) 0.0164(7) 0.0191(7) 0.0006(6) 0.0002(6) 0.0006(5)
    C9 0.0266(8) 0.0175(7) 0.0185(7) 0.0021(6) 0.0016(6) 0.0008(5)
    C10 0.0261(7) 0.0177(7) 0.0220(7) -0.0004(6) 0.0016(6) 0.0014(6)
    C11 0.0256(8) 0.0206(7) 0.0212(7) 0.0012(6) -0.0012(6) -0.0002(6)
    C12 0.0229(7) 0.0194(7) 0.0197(7) -0.0002(6) -0.0007(6) 0.0014(6)
    C13 0.0254(8) 0.0233(8) 0.0183(7) 0.0023(6) -0.0002(6) 0.0009(6)
    C14 0.0346(9) 0.0279(8) 0.0340(9) 0.0007(8) 0.0070(7) -0.0037(7)
    C15 0.0374(9) 0.0242(8) 0.0287(8) 0.0011(7) 0.0045(7) -0.0054(7)
    C16 0.0260(8) 0.0196(7) 0.0229(7) 0.0015(6) 0.0009(6) -0.0024(6)
    C17 0.0325(8) 0.0198(7) 0.0235(7) 0.0036(7) -0.0022(7) -0.0033(6)
    C18 0.0329(9) 0.0235(7) 0.0265(8) 0.0046(7) -0.0001(7) 0.0014(6)
    C19 0.0242(7) 0.0192(7) 0.0365(9) 0.0005(6) 0.0031(7) -0.0004(7)
    C20 0.0256(8) 0.0229(8) 0.0314(8) -0.0004(6) -0.0019(7) -0.0060(6)
    C21 0.0265(8) 0.0242(8) 0.0229(7) 0.0016(6) -0.0011(6) -0.0031(6)
_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
    O1 C10 . 1.4510(18) ?
    O1 C1 . 1.4634(19) ?
    O2 C11 . 1.3667(18) ?
    O2 C9 . 1.4573(17) ?
    O3 C11 . 1.2072(18) ?
    N1 C19 . 1.393(2) ?
    N1 H1A . 0.94(2) ?
    N1 H2B . 0.90(2) ?
    C1 C10 . 1.472(2) ?
    C1 C15 . 1.502(2) ?
    C1 C2 . 1.510(2) ?
    C2 C3 . 1.547(2) ?
    C2 H1 . 0.9900 ?
    C2 H2A . 0.9900 ?
    C3 C4 . 1.505(2) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C5 . 1.334(3) ?
    C4 H4 . 0.9500 ?
    C5 C14 . 1.504(2) ?
    C5 C6 . 1.511(2) ?
    C6 C7 . 1.539(2) ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C7 C8 . 1.545(2) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 C12 . 1.5101(19) ?
    C8 C9 . 1.561(2) ?
    C8 H8 . 1.0000 ?
    C9 C10 . 1.501(2) ?
    C9 H9 . 1.0000 ?
    C10 H10 . 1.0000 ?
    C11 C12 . 1.472(2) ?
    C12 C13 . 1.342(2) ?
    C13 C16 . 1.457(2) ?
    C13 H13 . 0.9500 ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C14 H14C . 0.9800 ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C15 H15C . 0.9800 ?
    C16 C21 . 1.401(2) ?
    C16 C17 . 1.403(2) ?
    C17 C18 . 1.383(2) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.404(2) ?
    C18 H18 . 0.9500 ?
    C19 C20 . 1.395(2) ?
    C20 C21 . 1.378(2) ?
    C20 H20 . 0.9500 ?
    C21 H21 . 0.9500 ?
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
    C10 O1 C1 . . 60.67(10) ?
    C11 O2 C9 . . 110.56(11) ?
    C19 N1 H1A . . 114.0(15) ?
    C19 N1 H2B . . 112.6(15) ?
    H1A N1 H2B . . 118(2) ?
    O1 C1 C10 . . 59.25(9) ?
    O1 C1 C15 . . 112.05(13) ?
    C10 C1 C15 . . 122.43(14) ?
    O1 C1 C2 . . 117.39(14) ?
    C10 C1 C2 . . 116.62(15) ?
    C15 C1 C2 . . 116.15(14) ?
    C1 C2 C3 . . 110.08(14) ?
    C1 C2 H1 . . 109.6 ?
    C3 C2 H1 . . 109.6 ?
    C1 C2 H2A . . 109.6 ?
    C3 C2 H2A . . 109.6 ?
    H1 C2 H2A . . 108.2 ?
    C4 C3 C2 . . 110.68(13) ?
    C4 C3 H3A . . 109.5 ?
    C2 C3 H3A . . 109.5 ?
    C4 C3 H3B . . 109.5 ?
    C2 C3 H3B . . 109.5 ?
    H3A C3 H3B . . 108.1 ?
    C5 C4 C3 . . 128.15(15) ?
    C5 C4 H4 . . 115.9 ?
    C3 C4 H4 . . 115.9 ?
    C4 C5 C14 . . 125.04(14) ?
    C4 C5 C6 . . 120.33(15) ?
    C14 C5 C6 . . 114.58(15) ?
    C5 C6 C7 . . 113.64(12) ?
    C5 C6 H6A . . 108.8 ?
    C7 C6 H6A . . 108.8 ?
    C5 C6 H6B . . 108.8 ?
    C7 C6 H6B . . 108.8 ?
    H6A C6 H6B . . 107.7 ?
    C6 C7 C8 . . 115.03(13) ?
    C6 C7 H7A . . 108.5 ?
    C8 C7 H7A . . 108.5 ?
    C6 C7 H7B . . 108.5 ?
    C8 C7 H7B . . 108.5 ?
    H7A C7 H7B . . 107.5 ?
    C12 C8 C7 . . 114.12(13) ?
    C12 C8 C9 . . 102.02(11) ?
    C7 C8 C9 . . 114.19(12) ?
    C12 C8 H8 . . 108.7 ?
    C7 C8 H8 . . 108.7 ?
    C9 C8 H8 . . 108.7 ?
    O2 C9 C10 . . 109.13(12) ?
    O2 C9 C8 . . 106.91(11) ?
    C10 C9 C8 . . 111.63(12) ?
    O2 C9 H9 . . 109.7 ?
    C10 C9 H9 . . 109.7 ?
    C8 C9 H9 . . 109.7 ?
    O1 C10 C1 . . 60.08(9) ?
    O1 C10 C9 . . 121.02(12) ?
    C1 C10 C9 . . 123.89(14) ?
    O1 C10 H10 . . 113.8 ?
    C1 C10 H10 . . 113.8 ?
    C9 C10 H10 . . 113.8 ?
    O3 C11 O2 . . 120.44(14) ?
    O3 C11 C12 . . 129.80(14) ?
    O2 C11 C12 . . 109.72(12) ?
    C13 C12 C11 . . 118.35(13) ?
    C13 C12 C8 . . 132.77(14) ?
    C11 C12 C8 . . 108.87(12) ?
    C12 C13 C16 . . 131.43(14) ?
    C12 C13 H13 . . 114.3 ?
    C16 C13 H13 . . 114.3 ?
    C5 C14 H14A . . 109.5 ?
    C5 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C5 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C1 C15 H15A . . 109.5 ?
    C1 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C1 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C21 C16 C17 . . 117.15(14) ?
    C21 C16 C13 . . 118.40(14) ?
    C17 C16 C13 . . 124.42(14) ?
    C18 C17 C16 . . 121.43(15) ?
    C18 C17 H17 . . 119.3 ?
    C16 C17 H17 . . 119.3 ?
    C17 C18 C19 . . 120.49(15) ?
    C17 C18 H18 . . 119.8 ?
    C19 C18 H18 . . 119.8 ?
    N1 C19 C20 . . 121.19(15) ?
    N1 C19 C18 . . 120.33(16) ?
    C20 C19 C18 . . 118.47(15) ?
    C21 C20 C19 . . 120.52(15) ?
    C21 C20 H20 . . 119.7 ?
    C19 C20 H20 . . 119.7 ?
    C20 C21 C16 . . 121.91(15) ?
    C20 C21 H21 . . 119.0 ?
    C16 C21 H21 . . 119.0 ?
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
    C10 O1 C1 C15 . . . . -115.61(15) ?
    C10 O1 C1 C2 . . . . 106.19(17) ?
    O1 C1 C2 C3 . . . . -158.44(14) ?
    C10 C1 C2 C3 . . . . -91.06(18) ?
    C15 C1 C2 C3 . . . . 65.05(19) ?
    C1 C2 C3 C4 . . . . 51.03(19) ?
    C2 C3 C4 C5 . . . . -110.84(19) ?
    C3 C4 C5 C14 . . . . -8.7(3) ?
    C3 C4 C5 C6 . . . . 168.64(15) ?
    C4 C5 C6 C7 . . . . -98.81(18) ?
    C14 C5 C6 C7 . . . . 78.79(18) ?
    C5 C6 C7 C8 . . . . 73.72(17) ?
    C6 C7 C8 C12 . . . . 144.91(13) ?
    C6 C7 C8 C9 . . . . -98.26(15) ?
    C11 O2 C9 C10 . . . . 135.27(13) ?
    C11 O2 C9 C8 . . . . 14.39(16) ?
    C12 C8 C9 O2 . . . . -12.50(15) ?
    C7 C8 C9 O2 . . . . -136.12(12) ?
    C12 C8 C9 C10 . . . . -131.78(13) ?
    C7 C8 C9 C10 . . . . 104.60(15) ?
    C1 O1 C10 C9 . . . . 113.87(16) ?
    C15 C1 C10 O1 . . . . 98.02(16) ?
    C2 C1 C10 O1 . . . . -107.50(15) ?
    O1 C1 C10 C9 . . . . -109.26(15) ?
    C15 C1 C10 C9 . . . . -11.2(2) ?
    C2 C1 C10 C9 . . . . 143.25(15) ?
    O2 C9 C10 O1 . . . . 49.00(18) ?
    C8 C9 C10 O1 . . . . 166.95(12) ?
    O2 C9 C10 C1 . . . . 121.71(15) ?
    C8 C9 C10 C1 . . . . -120.33(15) ?
    C9 O2 C11 O3 . . . . 171.96(15) ?
    C9 O2 C11 C12 . . . . -9.99(16) ?
    O3 C11 C12 C13 . . . . 0.4(3) ?
    O2 C11 C12 C13 . . . . -177.46(14) ?
    O3 C11 C12 C8 . . . . 179.14(17) ?
    O2 C11 C12 C8 . . . . 1.33(18) ?
    C7 C8 C12 C13 . . . . -50.8(2) ?
    C9 C8 C12 C13 . . . . -174.49(17) ?
    C7 C8 C12 C11 . . . . 130.63(13) ?
    C9 C8 C12 C11 . . . . 6.96(17) ?
    C11 C12 C13 C16 . . . . 174.88(16) ?
    C8 C12 C13 C16 . . . . -3.6(3) ?
    C12 C13 C16 C21 . . . . 163.27(17) ?
    C12 C13 C16 C17 . . . . -18.8(3) ?
    C21 C16 C17 C18 . . . . -2.0(2) ?
    C13 C16 C17 C18 . . . . -179.96(16) ?
    C16 C17 C18 C19 . . . . 0.9(3) ?
    C17 C18 C19 N1 . . . . -179.03(16) ?
    C17 C18 C19 C20 . . . . 0.4(2) ?
    N1 C19 C20 C21 . . . . 178.82(16) ?
    C18 C19 C20 C21 . . . . -0.6(2) ?
    C19 C20 C21 C16 . . . . -0.5(2) ?
    C17 C16 C21 C20 . . . . 1.8(2) ?
    C13 C16 C21 C20 . . . . 179.88(15) ?
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
    N1 H1A O1 1_545 0.94(2) 2.25(3) 3.133(2) 156(2)
    N1 H2B O2 1_545 0.90(2) 2.57(2) 3.077(2) 116(2)
    C2 H2A O3 3_566 0.99 2.63 3.372(2) 132
_shelx_hkl_checksum     86633
_shelx_hkl_file     {525abdbc-c321-4935-be6c-4d5a2b48da7a}
_shelx_res_checksum     75815
_shelxl_version_number         .2013
_iucr_refine_instructions_details
;
TITL x13354 - P212121
CELL  1.54178    8.5619   11.8846   17.7457    90.000    90.000    90.000
ZERR        4    0.0001    0.0002    0.0003     0.000     0.000     0.000
LATT  -1
SYMM     0.50000 - X ,            - Y ,    0.50000 + Z
SYMM     0.50000 + X ,    0.50000 - Y ,            - Z
SYMM             - X ,    0.50000 + Y ,    0.50000 - Z
SFAC  C  H  N  O
UNIT    84  100   4  12
REM FORM block
REM COLR colourless
SIZE 0.20 0.16 0.12
TEMP -183
L.S. 6
FMAP 2
PLAN 10
ACTA
BOND $H
CONF
REM Instructions for potential hydrogen bonds
EQIV $1 x, y-1, z
HTAB N1 O1_$1
HTAB N1 O2_$1
EQIV $2 x+1/2, -y+3/2, -z+1
HTAB C2 O3_$2
EQIV $3 x+1/2, -y+1/2, -z+1
HTAB C10 N1_$3
REM EXTI    0.001124 (SU = 0.00049, not significant).
WGHT    0.040100    0.303000
FVAR       0.28576
O1    4    0.696713    0.838506    0.570321    11.00000    0.03409    0.02081 =
         0.02578   -0.00282    0.00453   -0.00635
O2    4    0.577354    0.718198    0.437654    11.00000    0.03680    0.01739 =
         0.01989    0.00169    0.00000   -0.00195
O3    4    0.579013    0.653180    0.319453    11.00000    0.03581    0.02793 =
         0.01905    0.00431   -0.00061   -0.00269
N1    3    0.486085   -0.032701    0.454549    11.00000    0.03641    0.01907 =
         0.04153    0.00130    0.00201   -0.00107
H1A   2    0.538781   -0.054546    0.498905    11.00000   -1.50000
H2B   2    0.495060   -0.077128    0.413503    11.00000   -1.50000
C1    1    0.612445    0.790026    0.634304    11.00000    0.03098    0.02223 =
         0.02320   -0.00294    0.00287   -0.00573
C2    1    0.704013    0.768737    0.705589    11.00000    0.03386    0.03750 =
         0.02484   -0.00551   -0.00041   -0.00652
AFIX  23
H1    2    0.714258    0.839678    0.734409    11.00000   -1.20000
H2A   2    0.810197    0.742026    0.692641    11.00000   -1.20000
AFIX   0
C3    1    0.620173    0.679438    0.754401    11.00000    0.03426    0.04301 =
         0.02010    0.00050   -0.00297   -0.00225
AFIX  23
H3A   2    0.688119    0.657922    0.797180    11.00000   -1.20000
H3B   2    0.522653    0.711719    0.775164    11.00000   -1.20000
AFIX   0
C4    1    0.582128    0.576688    0.708350    11.00000    0.03204    0.02972 =
         0.02122    0.00484    0.00275    0.00657
AFIX  43
H4    2    0.668781    0.532454    0.692845    11.00000   -1.20000
AFIX   0
C5    1    0.441987    0.539928    0.686568    11.00000    0.03421    0.02199 =
         0.01830    0.00479    0.00334    0.00407
C6    1    0.428412    0.447289    0.628632    11.00000    0.03457    0.01941 =
         0.02359    0.00458    0.00694    0.00198
AFIX  23
H6A   2    0.343236    0.395707    0.643801    11.00000   -1.20000
H6B   2    0.526809    0.403545    0.628167    11.00000   -1.20000
AFIX   0
C7    1    0.395507    0.490415    0.548392    11.00000    0.02692    0.02030 =
         0.02377    0.00145    0.00236   -0.00033
AFIX  23
H7A   2    0.308961    0.545540    0.550791    11.00000   -1.20000
H7B   2    0.359660    0.426341    0.517218    11.00000   -1.20000
AFIX   0
C8    1    0.536000    0.546379    0.508660    11.00000    0.02371    0.01640 =
         0.01915    0.00056    0.00022    0.00063
AFIX  13
H8    2    0.634554    0.517821    0.532085    11.00000   -1.20000
AFIX   0
C9    1    0.535927    0.677576    0.512517    11.00000    0.02661    0.01748 =
         0.01850    0.00077    0.00159    0.00209
AFIX  13
H9    2    0.429291    0.705039    0.526307    11.00000   -1.20000
AFIX   0
C10   1    0.653111    0.720556    0.568491    11.00000    0.02608    0.01771 =
         0.02204    0.00135    0.00159   -0.00043
AFIX  13
H10   2    0.742315    0.667949    0.577540    11.00000   -1.20000
AFIX   0
C11   1    0.565861    0.633462    0.385884    11.00000    0.02562    0.02055 =
         0.02123   -0.00017   -0.00119    0.00121
C12   1    0.542774    0.525388    0.424794    11.00000    0.02294    0.01940 =
         0.01973    0.00137   -0.00068   -0.00022
C13   1    0.534927    0.431375    0.383105    11.00000    0.02540    0.02327 =
         0.01833    0.00088   -0.00025    0.00230
AFIX  43
H13   2    0.536349    0.444085    0.330257    11.00000   -1.20000
AFIX   0
C14   1    0.288424    0.586981    0.713008    11.00000    0.03456    0.02786 =
         0.03400   -0.00367    0.00700    0.00069
AFIX 137
H14A  2    0.307069    0.642888    0.752593    11.00000   -1.50000
H14B  2    0.223612    0.525977    0.733077    11.00000   -1.50000
H14C  2    0.234518    0.622742    0.670584    11.00000   -1.50000
AFIX   0
C15   1    0.453673    0.841786    0.644186    11.00000    0.03736    0.02423 =
         0.02865   -0.00536    0.00445    0.00105
AFIX 137
H15A  2    0.463917    0.914154    0.670193    11.00000   -1.50000
H15B  2    0.387808    0.791308    0.674136    11.00000   -1.50000
H15C  2    0.405727    0.853660    0.594674    11.00000   -1.50000
AFIX   0
C16   1    0.524613    0.313283    0.404500    11.00000    0.02598    0.01964 =
         0.02287   -0.00243    0.00091    0.00155
C17   1    0.564149    0.271042    0.475830    11.00000    0.03248    0.01981 =
         0.02348   -0.00327   -0.00224    0.00357
AFIX  43
H17   2    0.600279    0.321401    0.513573    11.00000   -1.20000
AFIX   0
C18   1    0.551656    0.157678    0.492379    11.00000    0.03287    0.02354 =
         0.02652    0.00138   -0.00014    0.00461
AFIX  43
H18   2    0.577712    0.131405    0.541351    11.00000   -1.20000
AFIX   0
C19   1    0.500759    0.081145    0.437351    11.00000    0.02419    0.01916 =
         0.03653   -0.00040    0.00306    0.00053
C20   1    0.464286    0.122075    0.365783    11.00000    0.02557    0.02289 =
         0.03144   -0.00603   -0.00188   -0.00045
AFIX  43
H20   2    0.430632    0.071517    0.327628    11.00000   -1.20000
AFIX   0
C21   1    0.476702    0.235258    0.350017    11.00000    0.02649    0.02418 =
         0.02288   -0.00307   -0.00113    0.00162
AFIX  43
H21   2    0.452060    0.261129    0.300779    11.00000   -1.20000
AFIX   0
HKLF 4 1  0 0 1 1 0 0 0 1 0
REM  x13354 - P212121
REM R1 =  0.0265 for    3267 Fo > 4sig(Fo)  and  0.0268 for all    3296 data
REM    234 parameters refined using      0 restraints
END
WGHT      0.0400      0.3038
REM Highest difference peak  0.126,  deepest hole -0.135,  1-sigma level  0.030
Q1    1   0.7534  0.6838  0.5556  11.00000  0.05    0.13
Q2    1   0.5926  0.7055  0.5408  11.00000  0.05    0.12
Q3    1   0.5766  0.5302  0.4624  11.00000  0.05    0.12
Q4    1   0.6216  0.8081  0.4373  11.00000  0.05    0.12
Q5    1   0.5148  0.5951  0.6729  11.00000  0.05    0.12
Q6    1   0.5052  0.5093  0.7450  11.00000  0.05    0.12
Q7    1   0.6343  0.1376  0.5441  11.00000  0.05    0.11
Q8    1   0.4583  0.1192  0.4795  11.00000  0.05    0.11
Q9    1   0.5375  0.5719  0.4034  11.00000  0.05    0.10
Q10   1   0.4993  0.2942  0.4420  11.00000  0.05    0.10
;