##############################################################################
###                                                                        ###
###        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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#                                                                            #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-02-14
_journal_date_accepted     2010-02-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      3
_journal_page_first     o651
_journal_page_last     o652
_journal_paper_category     QO
_journal_coeditor_code     SJ2731
_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
;
1-Methyl-4-[(1E,3E)-4-phenylbuta-1,3-dienyl]pyridinium iodide
monohydrate
;
_publ_section_title_footnote
;
 This paper is dedicated to His Majesty King Bhumibol Adulyadej of Thailand
(King Rama IX) for his sustainable development of the country.
;
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
;
    'Kullapa Chanawanno' ?
;     Crystal Materials Research Unit
      Department of Chemistry
      Faculty of Science
      Prince of Songkla University
      Hat-Yai, Songkhla 90112
      Thailand
;
    'Chanasuk Surasit' ?
;     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
;
1-Methyl-4-[(1E,3E)-4-phenylbuta-1,3-dienyl]pyridinium iodide
monohydrate
;
_chemical_name_common
;
4-[((1E,3E)-4-phenylbuta-1,3-dienyl)]-1-methylpyridinium iodide
monohydrate
;
_chemical_formula_moiety     'C16 H16 N +, I-, H2 O'
_chemical_formula_sum     'C16 H18 I N O'
_chemical_formula_iupac     'C16 H16 N +, I-, H2 O'
_chemical_formula_weight     367.21
_chemical_melting_point     ?
_chemical_melting_point_gt     496
_chemical_melting_point_lt     498
_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     32.5600(6)
_cell_length_b     12.6414(2)
_cell_length_c     16.5602(3)
_cell_angle_alpha     90.00
_cell_angle_beta     111.1800(10)
_cell_angle_gamma     90.00
_cell_volume     6355.81(19)
_cell_formula_units_Z     16
_cell_measurement_reflns_used     9279
_cell_measurement_theta_min     1.74
_cell_measurement_theta_max     30.00
_cell_measurement_temperature     100
_exptl_crystal_description     Block
_exptl_crystal_colour     Yellow
_exptl_crystal_size_max     0.55
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.535
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     2912
_exptl_absorpt_coefficient_mu     2.008
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.4074
_exptl_absorpt_correction_T_max     0.6943
_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 100.0(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     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     36570
_diffrn_reflns_av_R_equivalents     0.0313
_diffrn_reflns_av_sigmaI/netI     0.0299
_diffrn_reflns_theta_min     1.74
_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     -39
_diffrn_reflns_limit_h_max     45
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_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 > 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     9279
_reflns_number_gt     6818
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0670
_refine_ls_R_factor_gt     0.0462
_refine_ls_wR_factor_gt     0.1027
_refine_ls_wR_factor_ref     0.1170
_refine_ls_goodness_of_fit_ref     1.015
_refine_ls_restrained_S_all     1.015
_refine_ls_number_reflns     9279
_refine_ls_number_parameters     357
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'calc w=1/[σ²(Fo²)+(0.0415P)²+36.1246P] 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     0.003
_refine_ls_shift/su_mean     <0.001
_refine_diff_density_max     2.400
_refine_diff_density_min     -1.866
_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'
    'I' 'I' -0.4742 1.8119
                         '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
    I I1A 0.006481(8) 0.74812(2) 0.492960(16) 0.03922(8) Uani d . 1 . .
    I I1B 0.825988(11) 0.71635(2) 0.18855(3) 0.06328(12) Uani d . 1 . .
    N N1A 0.90440(10) 0.0474(2) 0.29244(19) 0.0305(6) Uani d . 1 . .
    C C1A 0.84641(12) 0.1693(3) 0.2688(2) 0.0302(7) Uani d . 1 . .
    H H1A 0.8356 0.2302 0.2856 0.036 Uiso calc R 1 . .
    C C2A 0.88809(12) 0.1352(3) 0.3159(2) 0.0303(7) Uani d . 1 . .
    H H2A 0.9053 0.1729 0.3646 0.036 Uiso calc R 1 . .
    C C3A 0.87910(13) -0.0101(3) 0.2239(2) 0.0368(8) Uani d . 1 . .
    H H3A 0.8904 -0.0719 0.2094 0.044 Uiso calc R 1 . .
    C C4A 0.83732(13) 0.0206(3) 0.1755(2) 0.0360(8) Uani d . 1 . .
    H H4A 0.8204 -0.0206 0.1289 0.043 Uiso calc R 1 . .
    C C5A 0.81968(12) 0.1135(3) 0.1953(2) 0.0303(7) Uani d . 1 . .
    C C6A 0.77644(12) 0.1532(3) 0.1426(2) 0.0348(8) Uani d . 1 . .
    H H6A 0.7662 0.2132 0.1619 0.042 Uiso calc R 1 . .
    C C7A 0.75006(13) 0.1094(3) 0.0677(3) 0.0378(8) Uani d . 1 . .
    H H7A 0.7597 0.0476 0.0497 0.045 Uiso calc R 1 . .
    C C8A 0.70796(12) 0.1511(3) 0.0135(2) 0.0358(8) Uani d . 1 . .
    H H8A 0.6976 0.2122 0.0310 0.043 Uiso calc R 1 . .
    C C9A 0.68303(12) 0.1052(3) -0.0615(2) 0.0340(7) Uani d . 1 . .
    H H9A 0.6943 0.0438 -0.0765 0.041 Uiso calc R 1 . .
    C C10A 0.64019(12) 0.1407(3) -0.1220(2) 0.0311(7) Uani d . 1 . .
    C C11A 0.62086(12) 0.0866(3) -0.2003(2) 0.0328(7) Uani d . 1 . .
    H H11A 0.6352 0.0286 -0.2125 0.039 Uiso calc R 1 . .
    C C12A 0.58082(12) 0.1182(3) -0.2597(3) 0.0367(8) Uani d . 1 . .
    H H12A 0.5686 0.0817 -0.3117 0.044 Uiso calc R 1 . .
    C C13A 0.55865(12) 0.2036(3) -0.2427(3) 0.0361(8) Uani d . 1 . .
    H H13A 0.5318 0.2254 -0.2832 0.043 Uiso calc R 1 . .
    C C14A 0.57699(12) 0.2566(3) -0.1641(2) 0.0338(7) Uani d . 1 . .
    H H14A 0.5618 0.3126 -0.1513 0.041 Uiso calc R 1 . .
    C C15A 0.61757(12) 0.2269(3) -0.1047(2) 0.0320(7) Uani d . 1 . .
    H H15A 0.6299 0.2642 -0.0532 0.038 Uiso calc R 1 . .
    C C16A 0.95039(13) 0.0138(3) 0.3392(3) 0.0380(8) Uani d . 1 . .
    H H16A 0.9642 0.0618 0.3861 0.057 Uiso calc R 1 . .
    H H16B 0.9662 0.0141 0.3002 0.057 Uiso calc R 1 . .
    H H16C 0.9506 -0.0563 0.3617 0.057 Uiso calc R 1 . .
    N N1B 0.07132(13) 0.4780(3) -0.0525(3) 0.0509(9) Uani d . 1 . .
    C C1B 0.12480(15) 0.5134(4) 0.0860(3) 0.0503(11) Uani d . 1 . .
    H H1B 0.1340 0.5532 0.1366 0.060 Uiso calc R 1 . .
    C C2B 0.08526(15) 0.5343(4) 0.0221(3) 0.0490(11) Uani d . 1 . .
    H H2B 0.0676 0.5881 0.0300 0.059 Uiso calc R 1 . .
    C C3B 0.09613(17) 0.4012(4) -0.0651(4) 0.0586(12) Uani d . 1 . .
    H H3B 0.0864 0.3634 -0.1168 0.070 Uiso calc R 1 . .
    C C4B 0.13613(17) 0.3770(4) -0.0025(4) 0.0595(13) Uani d . 1 . .
    H H4B 0.1531 0.3229 -0.0125 0.071 Uiso calc R 1 . .
    C C5B 0.15160(14) 0.4319(4) 0.0753(3) 0.0496(11) Uani d . 1 . .
    C C6B 0.19467(14) 0.4065(4) 0.1392(3) 0.0517(11) Uani d . 1 . .
    H H6B 0.2101 0.3507 0.1270 0.062 Uiso calc R 1 . .
    C C7B 0.21354(13) 0.4573(4) 0.2139(3) 0.0488(11) Uani d . 1 . .
    H H7B 0.1972 0.5097 0.2280 0.059 Uiso calc R 1 . .
    C C8B 0.25747(14) 0.4369(4) 0.2747(3) 0.0491(11) Uani d . 1 . .
    H H8B 0.2734 0.3806 0.2646 0.059 Uiso calc R 1 . .
    C C9B 0.27587(14) 0.4970(4) 0.3451(3) 0.0509(12) Uani d . 1 . .
    H H9B 0.2578 0.5473 0.3563 0.061 Uiso calc R 1 . .
    C C10B 0.32147(15) 0.4919(4) 0.4064(3) 0.0519(12) Uani d . 1 . .
    C C11B 0.35014(14) 0.4109(4) 0.4035(3) 0.0550(13) Uani d . 1 . .
    H H11B 0.3402 0.3554 0.3644 0.066 Uiso calc R 1 . .
    C C12B 0.39410(16) 0.4145(5) 0.4602(4) 0.0646(16) Uani d . 1 . .
    H H12B 0.4134 0.3607 0.4593 0.077 Uiso calc R 1 . .
    C C13B 0.40872(18) 0.4975(5) 0.5174(4) 0.0699(17) Uani d . 1 . .
    H H13B 0.4381 0.4997 0.5539 0.084 Uiso calc R 1 . .
    C C14B 0.3806(2) 0.5774(5) 0.5217(3) 0.0703(16) Uani d . 1 . .
    H H14B 0.3908 0.6328 0.5609 0.084 Uiso calc R 1 . .
    C C15B 0.33693(17) 0.5734(5) 0.4665(3) 0.0601(13) Uani d . 1 . .
    H H15B 0.3176 0.6260 0.4697 0.072 Uiso calc R 1 . .
    C C16B 0.02813(16) 0.5012(4) -0.1198(3) 0.0622(14) Uani d . 1 . .
    H H16D 0.0291 0.4851 -0.1758 0.093 Uiso calc R 1 . .
    H H16E 0.0213 0.5748 -0.1175 0.093 Uiso calc R 1 . .
    H H16F 0.0059 0.4589 -0.1100 0.093 Uiso calc R 1 . .
    O O1W 0.05902(16) 0.3235(5) 0.7242(3) 0.104(2) Uani d P 0.90 A 1
    H H1W1 0.0640 0.2698 0.7188 0.156 Uiso d PR 0.90 A 1
    H H2W1 0.0761 0.3618 0.7007 0.156 Uiso d PR 0.90 A 1
    O O2W 0.4677(3) 0.6439(6) 0.6879(4) 0.103(2) Uani d P 0.70 B 2
    H H1W2 0.4610 0.6930 0.7206 0.154 Uiso d PR 0.70 B 2
    H H2W2 0.4770 0.6733 0.6557 0.154 Uiso d PR 0.70 B 2
    O O3W 0.2541(4) 0.6530(9) 0.5171(7) 0.087(3) Uani d P 0.40 C 3
    H H1W3 0.2374 0.6726 0.4678 0.130 Uiso d PR 0.40 C 3
    H H2W3 0.2766 0.6895 0.5289 0.130 Uiso d PR 0.40 C 3
_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
    N1A C2A . 1.346(4) ?
    N1A C3A . 1.349(5) ?
    N1A C16A . 1.478(5) ?
    C1A C2A . 1.368(5) ?
    C1A C5A . 1.403(5) ?
    C1A H1A . 0.9300 ?
    C2A H2A . 0.9300 ?
    C3A C4A . 1.362(5) ?
    C3A H3A . 0.9300 ?
    C4A C5A . 1.397(5) ?
    C4A H4A . 0.9300 ?
    C5A C6A . 1.452(5) ?
    C6A C7A . 1.347(5) ?
    C6A H6A . 0.9300 ?
    C7A C8A . 1.440(5) ?
    C7A H7A . 0.9300 ?
    C8A C9A . 1.345(5) ?
    C8A H8A . 0.9300 ?
    C9A C10A . 1.464(5) ?
    C9A H9A . 0.9300 ?
    C10A C11A . 1.398(5) ?
    C10A C15A . 1.401(5) ?
    C11A C12A . 1.378(5) ?
    C11A H11A . 0.9300 ?
    C12A C13A . 1.384(5) ?
    C12A H12A . 0.9300 ?
    C13A C14A . 1.392(5) ?
    C13A H13A . 0.9300 ?
    C14A C15A . 1.384(5) ?
    C14A H14A . 0.9300 ?
    C15A H15A . 0.9300 ?
    C16A H16A . 0.9600 ?
    C16A H16B . 0.9600 ?
    C16A H16C . 0.9600 ?
    N1B C3B . 1.326(6) ?
    N1B C2B . 1.355(6) ?
    N1B C16B . 1.474(6) ?
    C1B C2B . 1.364(6) ?
    C1B C5B . 1.402(7) ?
    C1B H1B . 0.9300 ?
    C2B H2B . 0.9300 ?
    C3B C4B . 1.374(7) ?
    C3B H3B . 0.9300 ?
    C4B C5B . 1.388(7) ?
    C4B H4B . 0.9300 ?
    C5B C6B . 1.456(6) ?
    C6B C7B . 1.330(7) ?
    C6B H6B . 0.9300 ?
    C7B C8B . 1.444(6) ?
    C7B H7B . 0.9300 ?
    C8B C9B . 1.338(7) ?
    C8B H8B . 0.9300 ?
    C9B C10B . 1.466(6) ?
    C9B H9B . 0.9300 ?
    C10B C15B . 1.394(8) ?
    C10B C11B . 1.399(7) ?
    C11B C12B . 1.401(7) ?
    C11B H11B . 0.9300 ?
    C12B C13B . 1.378(9) ?
    C12B H12B . 0.9300 ?
    C13B C14B . 1.382(9) ?
    C13B H13B . 0.9300 ?
    C14B C15B . 1.387(8) ?
    C14B H14B . 0.9300 ?
    C15B H15B . 0.9300 ?
    C16B H16D . 0.9600 ?
    C16B H16E . 0.9600 ?
    C16B H16F . 0.9600 ?
    O1W H1W1 . 0.7106 ?
    O1W H2W1 . 0.9232 ?
    O2W H1W2 . 0.8994 ?
    O2W H2W2 . 0.7950 ?
    O3W H1W3 . 0.8376 ?
    O3W H2W3 . 0.8268 ?
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
    C2A N1A C3A . . 120.2(3) ?
    C2A N1A C16A . . 121.1(3) ?
    C3A N1A C16A . . 118.7(3) ?
    C2A C1A C5A . . 120.9(3) ?
    C2A C1A H1A . . 119.6 ?
    C5A C1A H1A . . 119.6 ?
    N1A C2A C1A . . 120.5(3) ?
    N1A C2A H2A . . 119.7 ?
    C1A C2A H2A . . 119.7 ?
    N1A C3A C4A . . 121.1(3) ?
    N1A C3A H3A . . 119.4 ?
    C4A C3A H3A . . 119.4 ?
    C3A C4A C5A . . 120.6(3) ?
    C3A C4A H4A . . 119.7 ?
    C5A C4A H4A . . 119.7 ?
    C4A C5A C1A . . 116.5(3) ?
    C4A C5A C6A . . 122.8(3) ?
    C1A C5A C6A . . 120.7(3) ?
    C7A C6A C5A . . 124.6(4) ?
    C7A C6A H6A . . 117.7 ?
    C5A C6A H6A . . 117.7 ?
    C6A C7A C8A . . 124.7(4) ?
    C6A C7A H7A . . 117.6 ?
    C8A C7A H7A . . 117.6 ?
    C9A C8A C7A . . 122.6(4) ?
    C9A C8A H8A . . 118.7 ?
    C7A C8A H8A . . 118.7 ?
    C8A C9A C10A . . 127.4(3) ?
    C8A C9A H9A . . 116.3 ?
    C10A C9A H9A . . 116.3 ?
    C11A C10A C15A . . 118.4(3) ?
    C11A C10A C9A . . 118.9(3) ?
    C15A C10A C9A . . 122.7(3) ?
    C12A C11A C10A . . 120.9(3) ?
    C12A C11A H11A . . 119.6 ?
    C10A C11A H11A . . 119.6 ?
    C11A C12A C13A . . 120.6(4) ?
    C11A C12A H12A . . 119.7 ?
    C13A C12A H12A . . 119.7 ?
    C12A C13A C14A . . 119.2(4) ?
    C12A C13A H13A . . 120.4 ?
    C14A C13A H13A . . 120.4 ?
    C15A C14A C13A . . 120.7(3) ?
    C15A C14A H14A . . 119.7 ?
    C13A C14A H14A . . 119.7 ?
    C14A C15A C10A . . 120.2(3) ?
    C14A C15A H15A . . 119.9 ?
    C10A C15A H15A . . 119.9 ?
    N1A C16A H16A . . 109.5 ?
    N1A C16A H16B . . 109.5 ?
    H16A C16A H16B . . 109.5 ?
    N1A C16A H16C . . 109.5 ?
    H16A C16A H16C . . 109.5 ?
    H16B C16A H16C . . 109.5 ?
    C3B N1B C2B . . 120.4(4) ?
    C3B N1B C16B . . 119.7(5) ?
    C2B N1B C16B . . 119.9(4) ?
    C2B C1B C5B . . 120.0(5) ?
    C2B C1B H1B . . 120.0 ?
    C5B C1B H1B . . 120.0 ?
    N1B C2B C1B . . 121.1(5) ?
    N1B C2B H2B . . 119.5 ?
    C1B C2B H2B . . 119.5 ?
    N1B C3B C4B . . 120.7(5) ?
    N1B C3B H3B . . 119.7 ?
    C4B C3B H3B . . 119.7 ?
    C3B C4B C5B . . 121.0(5) ?
    C3B C4B H4B . . 119.5 ?
    C5B C4B H4B . . 119.5 ?
    C4B C5B C1B . . 116.8(4) ?
    C4B C5B C6B . . 119.7(5) ?
    C1B C5B C6B . . 123.4(5) ?
    C7B C6B C5B . . 124.7(5) ?
    C7B C6B H6B . . 117.6 ?
    C5B C6B H6B . . 117.6 ?
    C6B C7B C8B . . 124.8(5) ?
    C6B C7B H7B . . 117.6 ?
    C8B C7B H7B . . 117.6 ?
    C9B C8B C7B . . 121.7(5) ?
    C9B C8B H8B . . 119.1 ?
    C7B C8B H8B . . 119.1 ?
    C8B C9B C10B . . 127.0(5) ?
    C8B C9B H9B . . 116.5 ?
    C10B C9B H9B . . 116.5 ?
    C15B C10B C11B . . 119.5(5) ?
    C15B C10B C9B . . 118.5(5) ?
    C11B C10B C9B . . 122.0(5) ?
    C10B C11B C12B . . 119.1(6) ?
    C10B C11B H11B . . 120.5 ?
    C12B C11B H11B . . 120.5 ?
    C13B C12B C11B . . 120.1(5) ?
    C13B C12B H12B . . 120.0 ?
    C11B C12B H12B . . 120.0 ?
    C12B C13B C14B . . 121.4(5) ?
    C12B C13B H13B . . 119.3 ?
    C14B C13B H13B . . 119.3 ?
    C13B C14B C15B . . 118.7(6) ?
    C13B C14B H14B . . 120.7 ?
    C15B C14B H14B . . 120.7 ?
    C14B C15B C10B . . 121.2(5) ?
    C14B C15B H15B . . 119.4 ?
    C10B C15B H15B . . 119.4 ?
    N1B C16B H16D . . 109.5 ?
    N1B C16B H16E . . 109.5 ?
    H16D C16B H16E . . 109.5 ?
    N1B C16B H16F . . 109.5 ?
    H16D C16B H16F . . 109.5 ?
    H16E C16B H16F . . 109.5 ?
    H1W1 O1W H2W1 . . 104.4 ?
    H1W2 O2W H2W2 . . 108.4 ?
    H1W3 O3W H2W3 . . 105.9 ?
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
    C3A N1A C2A C1A . . . . -2.6(5) ?
    C16A N1A C2A C1A . . . . 175.8(3) ?
    C5A C1A C2A N1A . . . . 0.3(5) ?
    C2A N1A C3A C4A . . . . 2.1(5) ?
    C16A N1A C3A C4A . . . . -176.2(4) ?
    N1A C3A C4A C5A . . . . 0.6(6) ?
    C3A C4A C5A C1A . . . . -2.7(5) ?
    C3A C4A C5A C6A . . . . 176.0(4) ?
    C2A C1A C5A C4A . . . . 2.3(5) ?
    C2A C1A C5A C6A . . . . -176.4(3) ?
    C4A C5A C6A C7A . . . . -3.9(6) ?
    C1A C5A C6A C7A . . . . 174.8(4) ?
    C5A C6A C7A C8A . . . . -177.3(3) ?
    C6A C7A C8A C9A . . . . 179.1(4) ?
    C7A C8A C9A C10A . . . . -179.3(4) ?
    C8A C9A C10A C11A . . . . 175.0(4) ?
    C8A C9A C10A C15A . . . . -5.1(6) ?
    C15A C10A C11A C12A . . . . 1.0(5) ?
    C9A C10A C11A C12A . . . . -179.2(3) ?
    C10A C11A C12A C13A . . . . -0.7(6) ?
    C11A C12A C13A C14A . . . . -0.9(6) ?
    C12A C13A C14A C15A . . . . 2.2(6) ?
    C13A C14A C15A C10A . . . . -1.9(6) ?
    C11A C10A C15A C14A . . . . 0.3(5) ?
    C9A C10A C15A C14A . . . . -179.5(3) ?
    C3B N1B C2B C1B . . . . -0.3(6) ?
    C16B N1B C2B C1B . . . . 179.0(4) ?
    C5B C1B C2B N1B . . . . -0.5(6) ?
    C2B N1B C3B C4B . . . . 0.5(7) ?
    C16B N1B C3B C4B . . . . -178.8(4) ?
    N1B C3B C4B C5B . . . . 0.0(7) ?
    C3B C4B C5B C1B . . . . -0.8(7) ?
    C3B C4B C5B C6B . . . . -178.2(4) ?
    C2B C1B C5B C4B . . . . 1.0(6) ?
    C2B C1B C5B C6B . . . . 178.3(4) ?
    C4B C5B C6B C7B . . . . 176.7(4) ?
    C1B C5B C6B C7B . . . . -0.6(7) ?
    C5B C6B C7B C8B . . . . -175.5(4) ?
    C6B C7B C8B C9B . . . . 174.2(4) ?
    C7B C8B C9B C10B . . . . -173.0(4) ?
    C8B C9B C10B C15B . . . . 168.2(4) ?
    C8B C9B C10B C11B . . . . -8.8(7) ?
    C15B C10B C11B C12B . . . . -1.1(6) ?
    C9B C10B C11B C12B . . . . 175.8(4) ?
    C10B C11B C12B C13B . . . . -0.6(6) ?
    C11B C12B C13B C14B . . . . 1.4(7) ?
    C12B C13B C14B C15B . . . . -0.4(7) ?
    C13B C14B C15B C10B . . . . -1.3(7) ?
    C11B C10B C15B C14B . . . . 2.1(6) ?
    C9B C10B C15B C14B . . . . -175.0(4) ?
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
    O2W H2W2 I1A 7_566 0.79 2.88 3.655(8) 166 y
    C3B H3B O1W 1_554 0.93 2.51 3.399(8) 161 y
    C16A H16A I1A 5_666 0.96 3.05 3.992(4) 167 y
