##############################################################################
###                                                                        ###
###        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/  #
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#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-07-02
_journal_date_accepted     2010-07-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      8
_journal_page_first     o1973
_journal_page_last     o1974
_journal_paper_category     QO
_journal_coeditor_code     FJ2326
_publ_contact_author_name     'Prof. Fun Hoong-Kun'
_publ_contact_author_address
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     'hkfun@usm.my'
_publ_contact_author_fax     '6 04 6579150'
_publ_contact_author_phone     '6 04 6577888  Ext. 3690'
_publ_section_title
;
(<i>E</i>)-1-(4-Aminophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Hoong-Kun Fun'
;
      Thomson Reuters ResearcherID: A-3561-2009.
;
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Thawanrat Kobkeatthawin' ?
;     Crystal Materials Research Unit
      Department of Chemistry
      Faculty of Science
      Prince of Songkla University
      Hat-Yai, Songkhla 90112
      Thailand
;
    'Pumsak Ruanwas' ?
;     Crystal Materials Research Unit
      Department of Chemistry
      Faculty of Science
      Prince of Songkla University
      Hat-Yai, Songkhla 90112
      Thailand
;
    'Suchada Chantrapromma'
;
      Additional correspondence author, e-mail: suchada.c@psu.ac.th.
      Thomson Reuters ResearcherID: A-5085-2009.
;
;     Crystal Materials Research Unit
      Department of Chemistry
      Faculty of Science
      Prince of Songkla University
      Hat-Yai, Songkhla 90112
      Thailand
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(<i>E</i>)-1-(4-Aminophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C18 H19 N O4'
_chemical_formula_sum     'C18 H19 N O4'
_chemical_formula_iupac     'C18 H19 N O4'
_chemical_formula_weight     313.34
_chemical_melting_point     ?
_chemical_melting_point_gt     393
_chemical_melting_point_lt     394
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     13.6117(2)
_cell_length_b     10.3540(2)
_cell_length_c     22.3920(4)
_cell_angle_alpha     90.00
_cell_angle_beta     100.8790(10)
_cell_angle_gamma     90.00
_cell_volume     3099.11(9)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     4506
_cell_measurement_theta_min     1.85
_cell_measurement_theta_max     30.00
_cell_measurement_temperature     100
_exptl_crystal_description     Block
_exptl_crystal_colour     Orange
_exptl_crystal_size_max     0.38
_exptl_crystal_size_mid     0.32
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.343
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1328
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.9647
_exptl_absorpt_correction_T_max     0.9910
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cryosystems Cobra
open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0(1) K.
;
_diffrn_ambient_temperature     100
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_method     '\f and \w scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19818
_diffrn_reflns_av_R_equivalents     0.0289
_diffrn_reflns_av_sigmaI/netI     0.0293
_diffrn_reflns_theta_min     1.85
_diffrn_reflns_theta_max     30.00
_diffrn_reflns_theta_full     30.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -31
_diffrn_reflns_limit_l_max     31
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     4506
_reflns_number_gt     3581
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0676
_refine_ls_R_factor_gt     0.0512
_refine_ls_wR_factor_gt     0.1205
_refine_ls_wR_factor_ref     0.1307
_refine_ls_goodness_of_fit_ref     1.048
_refine_ls_restrained_S_all     1.048
_refine_ls_number_reflns     4506
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0552P)^2^+3.4363P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_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     0.426
_refine_diff_density_min     -0.228
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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' 0.0000 0.0000
                         '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 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
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 0.38020(7) 0.71239(11) 0.65434(5) 0.0236(2) Uani d . 1 . .
    O O2 0.40102(7) 0.40284(10) 0.49618(5) 0.0226(2) Uani d . 1 . .
    O O3 0.10593(7) 0.26403(10) 0.35317(5) 0.0237(2) Uani d . 1 . .
    O O4 -0.00667(7) 0.42294(10) 0.40878(5) 0.0230(2) Uani d . 1 . .
    N N1 0.09228(9) 1.16277(13) 0.71073(6) 0.0226(3) Uani d . 1 . .
    H H1N1 0.0289(15) 1.1700(18) 0.6971(8) 0.028(5) Uiso d . 1 . .
    H H2N1 0.1136(15) 1.197(2) 0.7468(9) 0.036(5) Uiso d . 1 . .
    C C1 0.23640(9) 0.84035(13) 0.65403(6) 0.0165(3) Uani d . 1 . .
    C C2 0.28745(9) 0.92608(13) 0.69789(6) 0.0169(3) Uani d . 1 . .
    H H2A 0.3552 0.9129 0.7131 0.020 Uiso calc R 1 . .
    C C3 0.23973(10) 1.02891(13) 0.71892(6) 0.0174(3) Uani d . 1 . .
    H H3A 0.2749 1.0829 0.7486 0.021 Uiso calc R 1 . .
    C C4 0.13779(10) 1.05267(13) 0.69558(6) 0.0171(3) Uani d . 1 . .
    C C5 0.08494(9) 0.96364(14) 0.65447(6) 0.0183(3) Uani d . 1 . .
    H H5A 0.0166 0.9746 0.6407 0.022 Uiso calc R 1 . .
    C C6 0.13318(10) 0.86001(14) 0.63425(6) 0.0182(3) Uani d . 1 . .
    H H6A 0.0968 0.8020 0.6070 0.022 Uiso calc R 1 . .
    C C7 0.29247(10) 0.73650(13) 0.63014(6) 0.0177(3) Uani d . 1 . .
    C C8 0.24234(10) 0.66396(14) 0.57644(6) 0.0201(3) Uani d . 1 . .
    H H8A 0.1762 0.6835 0.5598 0.024 Uiso calc R 1 . .
    C C9 0.28853(9) 0.57075(13) 0.55064(6) 0.0177(3) Uani d . 1 . .
    H H9A 0.3553 0.5549 0.5673 0.021 Uiso calc R 1 . .
    C C10 0.24334(9) 0.49221(13) 0.49882(6) 0.0163(3) Uani d . 1 . .
    C C11 0.30112(9) 0.40495(13) 0.47178(6) 0.0174(3) Uani d . 1 . .
    C C12 0.25784(10) 0.32686(13) 0.42310(6) 0.0185(3) Uani d . 1 . .
    H H12A 0.2973 0.2697 0.4059 0.022 Uiso calc R 1 . .
    C C13 0.15546(10) 0.33465(13) 0.40038(6) 0.0181(3) Uani d . 1 . .
    C C14 0.09645(9) 0.42119(13) 0.42698(6) 0.0181(3) Uani d . 1 . .
    C C15 0.14011(10) 0.49721(13) 0.47490(6) 0.0177(3) Uani d . 1 . .
    H H15A 0.1002 0.5538 0.4921 0.021 Uiso calc R 1 . .
    C C16 0.46300(10) 0.31421(15) 0.47127(7) 0.0227(3) Uani d . 1 . .
    H H16A 0.5310 0.3231 0.4922 0.034 Uiso calc R 1 . .
    H H16B 0.4590 0.3324 0.4288 0.034 Uiso calc R 1 . .
    H H16C 0.4406 0.2276 0.4760 0.034 Uiso calc R 1 . .
    C C17 0.16178(11) 0.17238(15) 0.32512(7) 0.0249(3) Uani d . 1 . .
    H H17A 0.1189 0.1338 0.2908 0.037 Uiso calc R 1 . .
    H H17B 0.1877 0.1065 0.3540 0.037 Uiso calc R 1 . .
    H H17C 0.2162 0.2155 0.3118 0.037 Uiso calc R 1 . .
    C C18 -0.04143(12) 0.49413(19) 0.35457(8) 0.0338(4) Uani d . 1 . .
    H H18A -0.1129 0.5017 0.3482 0.051 Uiso calc R 1 . .
    H H18B -0.0228 0.4500 0.3207 0.051 Uiso calc R 1 . .
    H H18C -0.0120 0.5787 0.3582 0.051 Uiso calc R 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 0.0160(5) 0.0295(6) 0.0228(5) 0.0039(4) -0.0025(4) -0.0032(4)
    O2 0.0130(4) 0.0288(6) 0.0253(5) 0.0038(4) 0.0019(4) -0.0025(4)
    O3 0.0197(5) 0.0270(5) 0.0244(5) -0.0026(4) 0.0043(4) -0.0092(4)
    O4 0.0132(4) 0.0286(6) 0.0263(5) -0.0023(4) 0.0012(4) -0.0023(4)
    N1 0.0168(6) 0.0277(7) 0.0220(6) 0.0043(5) 0.0001(4) -0.0045(5)
    C1 0.0151(6) 0.0176(6) 0.0160(6) -0.0007(5) 0.0009(4) 0.0023(5)
    C2 0.0126(5) 0.0202(6) 0.0164(6) -0.0009(5) -0.0009(4) 0.0036(5)
    C3 0.0157(6) 0.0201(6) 0.0151(6) -0.0029(5) -0.0004(4) 0.0012(5)
    C4 0.0162(6) 0.0200(6) 0.0152(6) -0.0005(5) 0.0035(4) 0.0034(5)
    C5 0.0116(5) 0.0230(7) 0.0195(6) -0.0014(5) 0.0003(4) 0.0023(5)
    C6 0.0151(6) 0.0206(6) 0.0176(6) -0.0038(5) -0.0002(4) 0.0006(5)
    C7 0.0160(6) 0.0194(6) 0.0170(6) -0.0002(5) 0.0012(5) 0.0022(5)
    C8 0.0151(6) 0.0225(7) 0.0203(6) 0.0011(5) -0.0024(5) -0.0015(5)
    C9 0.0137(5) 0.0220(7) 0.0170(6) -0.0018(5) 0.0019(4) 0.0029(5)
    C10 0.0145(6) 0.0184(6) 0.0161(6) -0.0008(5) 0.0034(4) 0.0018(5)
    C11 0.0135(5) 0.0202(6) 0.0186(6) -0.0002(5) 0.0034(5) 0.0035(5)
    C12 0.0178(6) 0.0186(6) 0.0209(6) 0.0013(5) 0.0080(5) 0.0005(5)
    C13 0.0190(6) 0.0186(6) 0.0174(6) -0.0038(5) 0.0052(5) -0.0006(5)
    C14 0.0129(6) 0.0208(7) 0.0206(6) -0.0023(5) 0.0033(5) 0.0008(5)
    C15 0.0148(6) 0.0187(6) 0.0200(6) 0.0003(5) 0.0045(5) -0.0005(5)
    C16 0.0166(6) 0.0260(7) 0.0265(7) 0.0058(5) 0.0071(5) 0.0040(6)
    C17 0.0281(7) 0.0221(7) 0.0260(7) -0.0023(6) 0.0091(6) -0.0064(6)
    C18 0.0208(7) 0.0432(10) 0.0345(9) 0.0005(7) -0.0023(6) 0.0071(7)
_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 C7 . 1.2400(16) ?
    O2 C11 . 1.3666(15) ?
    O2 C16 . 1.4293(17) ?
    O3 C13 . 1.3557(16) ?
    O3 C17 . 1.4329(17) ?
    O4 C14 . 1.3859(15) ?
    O4 C18 . 1.4228(19) ?
    N1 C4 . 1.3704(18) ?
    N1 H1N1 . 0.862(19) ?
    N1 H2N1 . 0.88(2) ?
    C1 C6 . 1.4060(18) ?
    C1 C2 . 1.4064(18) ?
    C1 C7 . 1.4760(19) ?
    C2 C3 . 1.3758(19) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.4089(18) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.4016(19) ?
    C5 C6 . 1.378(2) ?
    C5 H5A . 0.9300 ?
    C6 H6A . 0.9300 ?
    C7 C8 . 1.4718(19) ?
    C8 C9 . 1.3407(19) ?
    C8 H8A . 0.9300 ?
    C9 C10 . 1.4549(18) ?
    C9 H9A . 0.9300 ?
    C10 C15 . 1.4071(18) ?
    C10 C11 . 1.4076(18) ?
    C11 C12 . 1.3953(19) ?
    C12 C13 . 1.3927(18) ?
    C12 H12A . 0.9300 ?
    C13 C14 . 1.4083(19) ?
    C14 C15 . 1.3724(19) ?
    C15 H15A . 0.9300 ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C18 H18C . 0.9600 ?
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
    C11 O2 C16 . . 118.06(11) ?
    C13 O3 C17 . . 118.17(11) ?
    C14 O4 C18 . . 114.38(11) ?
    C4 N1 H1N1 . . 117.0(13) ?
    C4 N1 H2N1 . . 118.4(13) ?
    H1N1 N1 H2N1 . . 115.1(18) ?
    C6 C1 C2 . . 117.47(12) ?
    C6 C1 C7 . . 123.07(12) ?
    C2 C1 C7 . . 119.46(11) ?
    C3 C2 C1 . . 121.63(12) ?
    C3 C2 H2A . . 119.2 ?
    C1 C2 H2A . . 119.2 ?
    C2 C3 C4 . . 120.24(12) ?
    C2 C3 H3A . . 119.9 ?
    C4 C3 H3A . . 119.9 ?
    N1 C4 C5 . . 120.65(12) ?
    N1 C4 C3 . . 120.86(12) ?
    C5 C4 C3 . . 118.44(12) ?
    C6 C5 C4 . . 120.69(12) ?
    C6 C5 H5A . . 119.7 ?
    C4 C5 H5A . . 119.7 ?
    C5 C6 C1 . . 121.26(12) ?
    C5 C6 H6A . . 119.4 ?
    C1 C6 H6A . . 119.4 ?
    O1 C7 C8 . . 120.93(12) ?
    O1 C7 C1 . . 120.63(12) ?
    C8 C7 C1 . . 118.43(11) ?
    C9 C8 C7 . . 122.45(12) ?
    C9 C8 H8A . . 118.8 ?
    C7 C8 H8A . . 118.8 ?
    C8 C9 C10 . . 125.73(12) ?
    C8 C9 H9A . . 117.1 ?
    C10 C9 H9A . . 117.1 ?
    C15 C10 C11 . . 117.31(12) ?
    C15 C10 C9 . . 121.64(12) ?
    C11 C10 C9 . . 121.02(12) ?
    O2 C11 C12 . . 123.00(12) ?
    O2 C11 C10 . . 115.65(12) ?
    C12 C11 C10 . . 121.35(12) ?
    C13 C12 C11 . . 119.84(12) ?
    C13 C12 H12A . . 120.1 ?
    C11 C12 H12A . . 120.1 ?
    O3 C13 C12 . . 124.72(12) ?
    O3 C13 C14 . . 115.69(12) ?
    C12 C13 C14 . . 119.59(12) ?
    C15 C14 O4 . . 119.17(12) ?
    C15 C14 C13 . . 119.88(12) ?
    O4 C14 C13 . . 120.72(12) ?
    C14 C15 C10 . . 122.04(12) ?
    C14 C15 H15A . . 119.0 ?
    C10 C15 H15A . . 119.0 ?
    O2 C16 H16A . . 109.5 ?
    O2 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    O2 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    O3 C17 H17A . . 109.5 ?
    O3 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    O3 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    O4 C18 H18A . . 109.5 ?
    O4 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    O4 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
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
    C6 C1 C2 C3 . . . . -2.81(19) ?
    C7 C1 C2 C3 . . . . 176.14(12) ?
    C1 C2 C3 C4 . . . . -1.5(2) ?
    C2 C3 C4 N1 . . . . -172.31(13) ?
    C2 C3 C4 C5 . . . . 5.09(19) ?
    N1 C4 C5 C6 . . . . 173.09(13) ?
    C3 C4 C5 C6 . . . . -4.31(19) ?
    C4 C5 C6 C1 . . . . -0.1(2) ?
    C2 C1 C6 C5 . . . . 3.6(2) ?
    C7 C1 C6 C5 . . . . -175.30(13) ?
    C6 C1 C7 O1 . . . . -170.62(13) ?
    C2 C1 C7 O1 . . . . 10.5(2) ?
    C6 C1 C7 C8 . . . . 10.37(19) ?
    C2 C1 C7 C8 . . . . -168.52(12) ?
    O1 C7 C8 C9 . . . . -1.0(2) ?
    C1 C7 C8 C9 . . . . 177.98(13) ?
    C7 C8 C9 C10 . . . . 177.99(13) ?
    C8 C9 C10 C15 . . . . -7.9(2) ?
    C8 C9 C10 C11 . . . . 174.10(14) ?
    C16 O2 C11 C12 . . . . -1.45(19) ?
    C16 O2 C11 C10 . . . . 178.80(12) ?
    C15 C10 C11 O2 . . . . 179.96(11) ?
    C9 C10 C11 O2 . . . . -1.95(18) ?
    C15 C10 C11 C12 . . . . 0.21(19) ?
    C9 C10 C11 C12 . . . . 178.30(12) ?
    O2 C11 C12 C13 . . . . -179.69(12) ?
    C10 C11 C12 C13 . . . . 0.0(2) ?
    C17 O3 C13 C12 . . . . 1.5(2) ?
    C17 O3 C13 C14 . . . . -178.72(12) ?
    C11 C12 C13 O3 . . . . 179.60(13) ?
    C11 C12 C13 C14 . . . . -0.2(2) ?
    C18 O4 C14 C15 . . . . 104.12(16) ?
    C18 O4 C14 C13 . . . . -81.36(17) ?
    O3 C13 C14 C15 . . . . -179.72(12) ?
    C12 C13 C14 C15 . . . . 0.1(2) ?
    O3 C13 C14 O4 . . . . 5.79(19) ?
    C12 C13 C14 O4 . . . . -174.38(12) ?
    O4 C14 C15 C10 . . . . 174.73(12) ?
    C13 C14 C15 C10 . . . . 0.2(2) ?
    C11 C10 C15 C14 . . . . -0.3(2) ?
    C9 C10 C15 C14 . . . . -178.39(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
    _geom_hbond_publ_flag
    N1 H1N1 O1 3_455 0.86(2) 2.12(2) 2.9692(16) 170.4(17) y
    N1 H2N1 O1 4_556 0.88(2) 2.21(2) 3.0176(17) 153.4(19) y