##############################################################################
###                                                                        ###
###        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     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2008-05-28
_journal_date_accepted     2008-05-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     o1211
_journal_page_last     o1211
_journal_paper_category     QO
_journal_coeditor_code     WN2266
_publ_contact_author_name
;
A. Thiruvalluvar
;
_publ_contact_author_address
;
PG Research Department of Physics
Rajah Serfoji Government College (Autonomous)
Thanjavur-613 005
Tamil Nadu
India
;
_publ_contact_author_email     athiru@vsnl.net
_publ_contact_author_fax     'none'
_publ_contact_author_phone     '+91(4362)255490'
_publ_section_title
;
t-3-Benzyl-r-2,c-6-bis(4-methoxyphenyl)piperidin-4-one oxime
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'J. Jayabharathi' .
;
Department of Chemistry
Annamalai University
Annamalai Nagar 608 002
Tamil Nadu
India
;
    'A. Thangamani' .
;
Department of Chemistry
Annamalai University
Annamalai Nagar 608 002
Tamil Nadu
India
;
    'S. Balamurugan' .
;
PG Research Department of Physics
Rajah Serfoji Government College (Autonomous)
Thanjavur 613 005
Tamil Nadu
India
;
    'A. Thiruvalluvar' .
;
PG Research Department of Physics
Rajah Serfoji Government College (Autonomous)
Thanjavur 613 005
Tamil Nadu
India
;
    'A. Linden' .
;
Institute of Organic Chemistry,
University of Zürich
Winterthurerstrasse 190,
CH-8057 Zürich,
Switzerland
;
data_I
_chemical_name_systematic
;
t-3-Benzyl-r-2,c-6-bis(4-methoxyphenyl)piperidin-4-one oxime
;
_chemical_name_common     'piperidin-4-one Oxime'
_chemical_formula_moiety     'C26 H28 N2 O3'
_chemical_formula_sum     'C26 H28 N2 O3'
_chemical_formula_structural     'C26 H28 N2 O3'
_chemical_formula_iupac     'C26 H28 N2 O3'
_chemical_formula_weight     416.50
_chemical_melting_point     460
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 1/2-x,-y,1/2+z
    3 1/2+x,1/2-y,-z
    4 -x,1/2+y,1/2-z
    5 -x,-y,-z
    6 1/2+x,y,1/2-z
    7 1/2-x,1/2+y,z
    8 x,1/2-y,1/2+z
_cell_length_a     10.2472(4)
_cell_length_b     11.2723(4)
_cell_length_c     38.4188(15)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     4437.7(3)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     4402
_cell_measurement_theta_min     2.0
_cell_measurement_theta_max     25.0
_cell_measurement_temperature     160.0(10)
_exptl_crystal_description     tablet
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.13
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.247
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1776
_exptl_absorpt_coefficient_mu     0.082
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
Solvent used: Ethanol Cooling Device: Oxford Cryosystems Cryostream 700 Crystal
mount: glued on a glass fibre Mosaicity (°.): 0.618(1) Frames collected: 629
Seconds exposure per frame: 35 Degrees rotation per frame: 1.0
Crystal-Detector distance (mm): 57.3
;
_diffrn_ambient_temperature     160.0(10)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Nonius FR590 sealed tube generator'
_diffrn_radiation_monochromator     'horizontally mounted graphite crystal'
_diffrn_measurement_device_type     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     'φ and ω scans with κ offsets'
_diffrn_detector_area_resol_mean     9
_diffrn_reflns_number     36542
_diffrn_reflns_av_R_equivalents     0.0920
_diffrn_reflns_av_sigmaI/netI     0.0912
_diffrn_reflns_theta_min     3.12
_diffrn_reflns_theta_max     25.03
_diffrn_reflns_theta_full     25.03
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -45
_diffrn_reflns_limit_l_max     45
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     3910
_reflns_number_gt     2305
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1356
_refine_ls_R_factor_gt     0.0703
_refine_ls_wR_factor_gt     0.1430
_refine_ls_wR_factor_ref     0.2109
_refine_ls_goodness_of_fit_ref     1.083
_refine_ls_restrained_S_all     1.083
_refine_ls_number_reflns     3910
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.1121P)²] 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     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.878
_refine_diff_density_min     -0.754
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.036(3)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    O O 0.0106 0.0060 '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'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 2000)'
_computing_cell_refinement     'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction
                            'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'PLATON (Spek, 2003)'
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    O O2 0.0668(2) 0.34156(19) 0.18566(6) 0.0420(8) Uani . . 1.000
    O O4 0.9150(2) 0.03452(19) 0.09433(6) 0.0386(8) Uani . . 1.000
    O O6 0.7048(2) 0.5478(2) -0.05739(5) 0.0443(9) Uani . . 1.000
    N N1 0.5498(3) 0.2892(2) 0.08373(6) 0.0311(9) Uani . . 1.000
    N N4 0.8055(2) 0.0468(2) 0.11664(6) 0.0335(9) Uani . . 1.000
    C C2 0.5128(3) 0.1965(3) 0.10941(8) 0.0322(11) Uani . . 1.000
    C C3 0.6286(3) 0.1719(3) 0.13407(8) 0.0301(10) Uani . . 1.000
    C C4 0.7480(3) 0.1470(3) 0.11248(8) 0.0315(11) Uani . . 1.000
    C C5 0.7802(3) 0.2386(3) 0.08540(8) 0.0354(11) Uani . . 1.000
    C C6 0.6613(3) 0.2506(3) 0.06163(8) 0.0332(11) Uani . . 1.000
    C C12 -0.0455(3) 0.2668(3) 0.18763(10) 0.0550(16) Uani . . 1.000
    C C13 0.5957(3) 0.0740(3) 0.16052(8) 0.0356(11) Uani . . 1.000
    C C16 0.8212(3) 0.6119(3) -0.06432(9) 0.0533(14) Uani . . 1.000
    C C21 0.3912(3) 0.2353(3) 0.12845(7) 0.0292(10) Uani . . 1.000
    C C22 0.3900(3) 0.3387(3) 0.14823(8) 0.0339(11) Uani . . 1.000
    C C23 0.2808(3) 0.3721(3) 0.16668(8) 0.0355(11) Uani . . 1.000
    C C24 0.1683(3) 0.3020(3) 0.16566(8) 0.0338(11) Uani . . 1.000
    C C25 0.1667(3) 0.1996(3) 0.14565(8) 0.0367(12) Uani . . 1.000
    C C26 0.2785(3) 0.1679(3) 0.12733(8) 0.0357(11) Uani . . 1.000
    C C31 0.6756(3) 0.0789(3) 0.19370(8) 0.0341(11) Uani . . 1.000
    C C32 0.6473(3) 0.1655(3) 0.21837(8) 0.0433(12) Uani . . 1.000
    C C33 0.7156(4) 0.1699(4) 0.24939(10) 0.0553(16) Uani . . 1.000
    C C34 0.8112(4) 0.0882(4) 0.25647(10) 0.0570(16) Uani . . 1.000
    C C35 0.8412(4) 0.0025(3) 0.23256(10) 0.0537(14) Uani . . 1.000
    C C36 0.7748(3) -0.0020(3) 0.20113(9) 0.0433(12) Uani . . 1.000
    C C61 0.6775(3) 0.3337(3) 0.03083(8) 0.0323(11) Uani . . 1.000
    C C62 0.7835(3) 0.4086(3) 0.02694(8) 0.0413(12) Uani . . 1.000
    C C63 0.7969(3) 0.4812(3) -0.00223(8) 0.0413(12) Uani . . 1.000
    C C64 0.7021(3) 0.4801(3) -0.02775(8) 0.0350(11) Uani . . 1.000
    C C65 0.5951(3) 0.4067(3) -0.02416(8) 0.0420(12) Uani . . 1.000
    C C66 0.5834(3) 0.3338(3) 0.00450(8) 0.0377(12) Uani . . 1.000
    H H1 0.473(3) 0.304(2) 0.0698(8) 0.030(8) Uiso . . 1.000
    H H2 0.49258 0.12179 0.09644 0.0385 Uiso . . 1.000
    H H3 0.64551 0.24632 0.14749 0.0362 Uiso . . 1.000
    H H4 0.94084 -0.03620 0.09464 0.0578 Uiso . . 1.000
    H H5A 0.85738 0.21356 0.07175 0.0422 Uiso . . 1.000
    H H5B 0.79998 0.31560 0.09663 0.0422 Uiso . . 1.000
    H H6 0.64031 0.17003 0.05231 0.0397 Uiso . . 1.000
    H H12A -0.11135 0.30392 0.20258 0.0825 Uiso . . 1.000
    H H12B -0.02061 0.18972 0.19741 0.0825 Uiso . . 1.000
    H H12C -0.08165 0.25535 0.16425 0.0825 Uiso . . 1.000
    H H13A 0.50211 0.08010 0.16667 0.0426 Uiso . . 1.000
    H H13B 0.60941 -0.00410 0.14934 0.0426 Uiso . . 1.000
    H H16A 0.81134 0.65636 -0.08607 0.0794 Uiso . . 1.000
    H H16B 0.89431 0.55628 -0.06650 0.0794 Uiso . . 1.000
    H H16C 0.83840 0.66712 -0.04517 0.0794 Uiso . . 1.000
    H H22 0.46583 0.38715 0.14903 0.0407 Uiso . . 1.000
    H H23 0.28182 0.44291 0.18010 0.0423 Uiso . . 1.000
    H H25 0.09043 0.15182 0.14448 0.0437 Uiso . . 1.000
    H H26 0.27738 0.09781 0.11362 0.0430 Uiso . . 1.000
    H H32 0.58053 0.22197 0.21388 0.0523 Uiso . . 1.000
    H H33 0.69611 0.23001 0.26593 0.0666 Uiso . . 1.000
    H H34 0.85656 0.09114 0.27801 0.0684 Uiso . . 1.000
    H H35 0.90752 -0.05401 0.23749 0.0643 Uiso . . 1.000
    H H36 0.79716 -0.06079 0.18445 0.0518 Uiso . . 1.000
    H H62 0.84854 0.41066 0.04454 0.0494 Uiso . . 1.000
    H H63 0.87098 0.53122 -0.00453 0.0494 Uiso . . 1.000
    H H65 0.52922 0.40631 -0.04155 0.0504 Uiso . . 1.000
    H H66 0.50995 0.28279 0.00639 0.0456 Uiso . . 1.000
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O2 C12 . . 1.428(4) no
    O2 C24 . . 1.368(4) no
    O4 N4 . . 1.419(3) no
    O6 C16 . . 1.420(4) no
    O6 C64 . . 1.371(4) no
    O4 H4 . . 0.8400 no
    N1 C6 . . 1.489(4) no
    N1 C2 . . 1.486(4) no
    N4 C4 . . 1.284(4) no
    N1 H1 . . 0.97(3) no
    C2 C3 . . 1.544(4) no
    C2 C21 . . 1.510(4) no
    C3 C13 . . 1.538(5) no
    C3 C4 . . 1.505(4) no
    C4 C5 . . 1.503(5) no
    C5 C6 . . 1.529(4) no
    C6 C61 . . 1.518(5) no
    C13 C31 . . 1.516(4) no
    C21 C22 . . 1.392(5) no
    C21 C26 . . 1.383(4) no
    C22 C23 . . 1.377(4) no
    C23 C24 . . 1.398(4) no
    C24 C25 . . 1.387(5) no
    C25 C26 . . 1.391(4) no
    C31 C36 . . 1.395(5) no
    C31 C32 . . 1.391(5) no
    C32 C33 . . 1.383(5) no
    C33 C34 . . 1.372(6) no
    C34 C35 . . 1.368(6) no
    C35 C36 . . 1.387(5) no
    C61 C66 . . 1.398(4) no
    C61 C62 . . 1.384(5) no
    C62 C63 . . 1.395(5) no
    C63 C64 . . 1.380(4) no
    C64 C65 . . 1.381(5) no
    C65 C66 . . 1.379(5) no
    C2 H2 . . 1.0000 no
    C3 H3 . . 1.0000 no
    C5 H5A . . 0.9900 no
    C5 H5B . . 0.9900 no
    C6 H6 . . 1.0000 no
    C12 H12A . . 0.9800 no
    C12 H12B . . 0.9800 no
    C12 H12C . . 0.9800 no
    C13 H13A . . 0.9900 no
    C13 H13B . . 0.9900 no
    C16 H16A . . 0.9800 no
    C16 H16B . . 0.9800 no
    C16 H16C . . 0.9800 no
    C22 H22 . . 0.9500 no
    C23 H23 . . 0.9500 no
    C25 H25 . . 0.9500 no
    C26 H26 . . 0.9500 no
    C32 H32 . . 0.9500 no
    C33 H33 . . 0.9500 no
    C34 H34 . . 0.9500 no
    C35 H35 . . 0.9500 no
    C36 H36 . . 0.9500 no
    C62 H62 . . 0.9500 no
    C63 H63 . . 0.9500 no
    C65 H65 . . 0.9500 no
    C66 H66 . . 0.9500 no
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    O2 C13 3.251(4) . 7_555 no
    O4 N1 2.818(3) . 7_645 no
    O4 C65 3.334(4) . 3_555 no
    O2 H13B 2.8700 . 7_555 no
    O2 H33 2.6100 . 6_455 no
    O2 H13A 2.8700 . 7_555 no
    O4 H65 2.4300 . 3_555 no
    O4 H5A 2.2700 . . no
    O6 H26 2.8100 . 3_555 no
    O6 H1 2.52(3) . 5_665 no
    N1 O4 2.818(3) . 7_655 no
    N4 C31 3.266(4) . . no
    N4 C36 3.307(4) . . no
    N1 H4 2.0100 . 7_655 no
    N1 H22 2.8700 . . no
    N4 H13B 2.4400 . . no
    N4 H36 2.8700 . . no
    N4 H5B 2.9200 . 7_645 no
    C12 C36 3.583(5) . 1_455 no
    C12 C31 3.565(5) . 1_455 no
    C12 C32 3.551(4) . 1_455 no
    C12 C36 3.547(5) . 7_555 no
    C12 C33 3.580(5) . 1_455 no
    C13 O2 3.251(4) . 7_545 no
    C31 C12 3.565(5) . 1_655 no
    C31 N4 3.266(4) . . no
    C32 C12 3.551(4) . 1_655 no
    C33 C12 3.580(5) . 1_655 no
    C36 C12 3.583(5) . 1_655 no
    C36 C12 3.547(5) . 7_545 no
    C36 N4 3.307(4) . . no
    C65 O4 3.334(4) . 3_455 no
    C65 C66 3.532(5) . 5_665 no
    C65 C65 3.416(5) . 5_665 no
    C66 C65 3.532(5) . 5_665 no
    C3 H22 3.0000 . . no
    C4 H12C 2.9100 . 1_655 no
    C5 H62 2.5900 . . no
    C6 H4 2.9100 . 7_655 no
    C12 H33 3.0800 . 6_455 no
    C12 H13B 3.0400 . 7_555 no
    C12 H25 2.5200 . . no
    C16 H26 3.0600 . 3_555 no
    C16 H63 2.5200 . . no
    C21 H13A 2.5500 . . no
    C21 H16A 2.9100 . 5_665 no
    C22 H3 2.8200 . . no
    C22 H4 3.0400 . 7_655 no
    C24 H33 2.7700 . 6_455 no
    C25 H16A 2.8200 . 5_665 no
    C25 H12C 2.7200 . . no
    C25 H12B 2.7700 . . no
    C26 H13A 2.9200 . . no
    C26 H16A 2.7000 . 5_665 no
    C32 H34 3.1000 . 6_455 no
    C32 H3 2.8700 . . no
    C32 H12A 2.9900 . 1_655 no
    C33 H12A 2.9400 . 1_655 no
    C34 H12B 3.0700 . 1_655 no
    C34 H23 3.0900 . 4_645 no
    C35 H12B 2.8800 . 1_655 no
    C36 H12B 3.0100 . 1_655 no
    C36 H12A 2.7600 . 7_545 no
    C62 H5B 2.8800 . . no
    C62 H5A 2.8900 . . no
    C63 H16B 2.7900 . . no
    C63 H6 3.0600 . 7_655 no
    C63 H16C 2.7000 . . no
    C65 H16C 2.9000 . 7_645 no
    C66 H1 2.77(3) . . no
    C66 H16C 2.8000 . 7_645 no
    H1 C66 2.77(3) . . no
    H1 H66 2.4800 . . no
    H1 O6 2.52(3) . 5_665 no
    H1 H4 2.2200 . 7_655 no
    H2 H6 2.3400 . . no
    H2 H26 2.3200 . . no
    H2 H16B 2.5200 . 3_455 no
    H3 C22 2.8200 . . no
    H3 C32 2.8700 . . no
    H3 H22 2.4300 . . no
    H4 N1 2.0100 . 7_645 no
    H4 C6 2.9100 . 7_645 no
    H4 C22 3.0400 . 7_645 no
    H4 H1 2.2200 . 7_645 no
    H4 H22 2.4600 . 7_645 no
    H5A O4 2.2700 . . no
    H5A C62 2.8900 . . no
    H5A H62 2.4600 . . no
    H5A H65 2.5000 . 3_555 no
    H5B C62 2.8800 . . no
    H5B H62 2.3200 . . no
    H5B N4 2.9200 . 7_655 no
    H6 H2 2.3400 . . no
    H6 H66 2.5500 . . no
    H6 C63 3.0600 . 7_645 no
    H12A C32 2.9900 . 1_455 no
    H12A C33 2.9400 . 1_455 no
    H12A C36 2.7600 . 7_555 no
    H12A H36 2.5400 . 7_555 no
    H12B C25 2.7700 . . no
    H12B C34 3.0700 . 1_455 no
    H12B C35 2.8800 . 1_455 no
    H12B C36 3.0100 . 1_455 no
    H12B H25 2.3700 . . no
    H12C C4 2.9100 . 1_455 no
    H12C C25 2.7200 . . no
    H12C H25 2.2500 . . no
    H13A C21 2.5500 . . no
    H13A C26 2.9200 . . no
    H13A H32 2.5500 . . no
    H13A H34 2.6000 . 6_455 no
    H13A O2 2.8700 . 7_545 no
    H13B N4 2.4400 . . no
    H13B H36 2.4400 . . no
    H13B O2 2.8700 . 7_545 no
    H13B C12 3.0400 . 7_545 no
    H16A C21 2.9100 . 5_665 no
    H16A C25 2.8200 . 5_665 no
    H16A C26 2.7000 . 5_665 no
    H16B C63 2.7900 . . no
    H16B H63 2.4100 . . no
    H16B H2 2.5200 . 3_555 no
    H16C C63 2.7000 . . no
    H16C H63 2.2100 . . no
    H16C C65 2.9000 . 7_655 no
    H16C C66 2.8000 . 7_655 no
    H22 N1 2.8700 . . no
    H22 C3 3.0000 . . no
    H22 H3 2.4300 . . no
    H22 H4 2.4600 . 7_655 no
    H23 C34 3.0900 . 4_655 no
    H25 C12 2.5200 . . no
    H25 H12B 2.3700 . . no
    H25 H12C 2.2500 . . no
    H26 H2 2.3200 . . no
    H26 O6 2.8100 . 3_455 no
    H26 C16 3.0600 . 3_455 no
    H32 H13A 2.5500 . . no
    H33 O2 2.6100 . 6_555 no
    H33 C12 3.0800 . 6_555 no
    H33 C24 2.7700 . 6_555 no
    H34 C32 3.1000 . 6_555 no
    H34 H13A 2.6000 . 6_555 no
    H36 N4 2.8700 . . no
    H36 H13B 2.4400 . . no
    H36 H12A 2.5400 . 7_545 no
    H62 C5 2.5900 . . no
    H62 H5A 2.4600 . . no
    H62 H5B 2.3200 . . no
    H63 C16 2.5200 . . no
    H63 H16B 2.4100 . . no
    H63 H16C 2.2100 . . no
    H65 O4 2.4300 . 3_455 no
    H65 H5A 2.5000 . 3_455 no
    H66 H1 2.4800 . . no
    H66 H6 2.5500 . . no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C12 O2 C24 . . . 116.8(2) no
    C16 O6 C64 . . . 117.1(2) no
    N4 O4 H4 . . . 109.00 no
    C2 N1 C6 . . . 111.7(2) no
    O4 N4 C4 . . . 111.9(2) no
    C6 N1 H1 . . . 111.1(18) no
    C2 N1 H1 . . . 106.3(17) no
    N1 C2 C3 . . . 109.7(3) no
    N1 C2 C21 . . . 109.2(3) no
    C3 C2 C21 . . . 112.9(2) no
    C2 C3 C4 . . . 108.7(2) no
    C2 C3 C13 . . . 111.5(3) no
    C4 C3 C13 . . . 114.1(3) no
    N4 C4 C5 . . . 126.2(3) no
    N4 C4 C3 . . . 118.0(3) no
    C3 C4 C5 . . . 115.6(3) no
    C4 C5 C6 . . . 107.4(3) no
    N1 C6 C5 . . . 107.3(2) no
    C5 C6 C61 . . . 115.7(3) no
    N1 C6 C61 . . . 110.4(3) no
    C3 C13 C31 . . . 114.3(3) no
    C22 C21 C26 . . . 118.0(3) no
    C2 C21 C26 . . . 121.0(3) no
    C2 C21 C22 . . . 121.0(3) no
    C21 C22 C23 . . . 121.2(3) no
    C22 C23 C24 . . . 120.1(3) no
    O2 C24 C23 . . . 115.3(3) no
    O2 C24 C25 . . . 125.0(3) no
    C23 C24 C25 . . . 119.7(3) no
    C24 C25 C26 . . . 119.0(3) no
    C21 C26 C25 . . . 122.1(3) no
    C13 C31 C32 . . . 119.1(3) no
    C13 C31 C36 . . . 122.8(3) no
    C32 C31 C36 . . . 118.1(3) no
    C31 C32 C33 . . . 120.5(3) no
    C32 C33 C34 . . . 120.5(4) no
    C33 C34 C35 . . . 120.1(4) no
    C34 C35 C36 . . . 120.0(3) no
    C31 C36 C35 . . . 120.8(3) no
    C6 C61 C62 . . . 123.1(3) no
    C6 C61 C66 . . . 119.3(3) no
    C62 C61 C66 . . . 117.6(3) no
    C61 C62 C63 . . . 121.5(3) no
    C62 C63 C64 . . . 119.8(3) no
    O6 C64 C65 . . . 115.6(3) no
    O6 C64 C63 . . . 124.8(3) no
    C63 C64 C65 . . . 119.6(3) no
    C64 C65 C66 . . . 120.4(3) no
    C61 C66 C65 . . . 121.2(3) no
    N1 C2 H2 . . . 108.00 no
    C3 C2 H2 . . . 108.00 no
    C21 C2 H2 . . . 108.00 no
    C2 C3 H3 . . . 107.00 no
    C4 C3 H3 . . . 107.00 no
    C13 C3 H3 . . . 107.00 no
    C4 C5 H5A . . . 110.00 no
    C4 C5 H5B . . . 110.00 no
    C6 C5 H5A . . . 110.00 no
    C6 C5 H5B . . . 110.00 no
    H5A C5 H5B . . . 108.00 no
    N1 C6 H6 . . . 108.00 no
    C5 C6 H6 . . . 108.00 no
    C61 C6 H6 . . . 108.00 no
    O2 C12 H12A . . . 110.00 no
    O2 C12 H12B . . . 109.00 no
    O2 C12 H12C . . . 109.00 no
    H12A C12 H12B . . . 109.00 no
    H12A C12 H12C . . . 109.00 no
    H12B C12 H12C . . . 109.00 no
    C3 C13 H13A . . . 109.00 no
    C3 C13 H13B . . . 109.00 no
    C31 C13 H13A . . . 109.00 no
    C31 C13 H13B . . . 109.00 no
    H13A C13 H13B . . . 108.00 no
    O6 C16 H16A . . . 109.00 no
    O6 C16 H16B . . . 109.00 no
    O6 C16 H16C . . . 109.00 no
    H16A C16 H16B . . . 109.00 no
    H16A C16 H16C . . . 110.00 no
    H16B C16 H16C . . . 109.00 no
    C21 C22 H22 . . . 119.00 no
    C23 C22 H22 . . . 119.00 no
    C22 C23 H23 . . . 120.00 no
    C24 C23 H23 . . . 120.00 no
    C24 C25 H25 . . . 121.00 no
    C26 C25 H25 . . . 121.00 no
    C21 C26 H26 . . . 119.00 no
    C25 C26 H26 . . . 119.00 no
    C31 C32 H32 . . . 120.00 no
    C33 C32 H32 . . . 120.00 no
    C32 C33 H33 . . . 120.00 no
    C34 C33 H33 . . . 120.00 no
    C33 C34 H34 . . . 120.00 no
    C35 C34 H34 . . . 120.00 no
    C34 C35 H35 . . . 120.00 no
    C36 C35 H35 . . . 120.00 no
    C31 C36 H36 . . . 120.00 no
    C35 C36 H36 . . . 120.00 no
    C61 C62 H62 . . . 119.00 no
    C63 C62 H62 . . . 119.00 no
    C62 C63 H63 . . . 120.00 no
    C64 C63 H63 . . . 120.00 no
    C64 C65 H65 . . . 120.00 no
    C66 C65 H65 . . . 120.00 no
    C61 C66 H66 . . . 119.00 no
    C65 C66 H66 . . . 119.00 no
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
    C12 O2 C24 C23 . . . . -174.7(3) no
    C12 O2 C24 C25 . . . . 4.3(4) no
    C16 O6 C64 C63 . . . . 8.4(4) no
    C16 O6 C64 C65 . . . . -171.6(3) no
    C6 N1 C2 C3 . . . . 61.5(3) no
    C6 N1 C2 C21 . . . . -174.2(2) no
    C2 N1 C6 C5 . . . . -65.7(3) no
    C2 N1 C6 C61 . . . . 167.5(2) no
    O4 N4 C4 C3 . . . . 179.1(2) no
    O4 N4 C4 C5 . . . . 5.6(4) no
    N1 C2 C3 C4 . . . . -51.9(3) no
    N1 C2 C3 C13 . . . . -178.5(2) no
    C21 C2 C3 C4 . . . . -173.9(3) no
    C21 C2 C3 C13 . . . . 59.5(4) no
    N1 C2 C21 C22 . . . . -61.0(4) no
    N1 C2 C21 C26 . . . . 120.4(3) no
    C3 C2 C21 C22 . . . . 61.4(4) no
    C3 C2 C21 C26 . . . . -117.3(3) no
    C2 C3 C4 N4 . . . . -121.5(3) no
    C2 C3 C4 C5 . . . . 52.7(4) no
    C13 C3 C4 N4 . . . . 3.6(4) no
    C13 C3 C4 C5 . . . . 177.8(3) no
    C2 C3 C13 C31 . . . . -155.9(3) no
    C4 C3 C13 C31 . . . . 80.5(3) no
    N4 C4 C5 C6 . . . . 116.3(3) no
    C3 C4 C5 C6 . . . . -57.3(3) no
    C4 C5 C6 N1 . . . . 60.3(3) no
    C4 C5 C6 C61 . . . . -176.1(3) no
    N1 C6 C61 C62 . . . . 112.1(3) no
    N1 C6 C61 C66 . . . . -69.4(4) no
    C5 C6 C61 C62 . . . . -9.9(5) no
    C5 C6 C61 C66 . . . . 168.6(3) no
    C3 C13 C31 C32 . . . . 74.9(4) no
    C3 C13 C31 C36 . . . . -106.8(4) no
    C2 C21 C22 C23 . . . . -177.6(3) no
    C26 C21 C22 C23 . . . . 1.2(5) no
    C2 C21 C26 C25 . . . . 177.7(3) no
    C22 C21 C26 C25 . . . . -1.0(5) no
    C21 C22 C23 C24 . . . . -0.2(5) no
    C22 C23 C24 O2 . . . . 178.3(3) no
    C22 C23 C24 C25 . . . . -0.8(5) no
    O2 C24 C25 C26 . . . . -178.1(3) no
    C23 C24 C25 C26 . . . . 0.9(5) no
    C24 C25 C26 C21 . . . . 0.0(5) no
    C13 C31 C32 C33 . . . . 177.9(3) no
    C36 C31 C32 C33 . . . . -0.4(5) no
    C13 C31 C36 C35 . . . . -176.9(3) no
    C32 C31 C36 C35 . . . . 1.4(5) no
    C31 C32 C33 C34 . . . . -0.7(6) no
    C32 C33 C34 C35 . . . . 1.0(6) no
    C33 C34 C35 C36 . . . . -0.1(6) no
    C34 C35 C36 C31 . . . . -1.1(5) no
    C6 C61 C62 C63 . . . . 178.1(3) no
    C66 C61 C62 C63 . . . . -0.4(5) no
    C6 C61 C66 C65 . . . . -179.1(3) no
    C62 C61 C66 C65 . . . . -0.6(5) no
    C61 C62 C63 C64 . . . . 0.8(5) no
    C62 C63 C64 O6 . . . . 179.8(3) no
    C62 C63 C64 C65 . . . . -0.2(5) no
    O6 C64 C65 C66 . . . . 179.3(3) no
    C63 C64 C65 C66 . . . . -0.8(5) no
    C64 C65 C66 C61 . . . . 1.2(5) no
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 H1 O6 5_665 0.97(3) 2.52(3) 3.348(3) 144(2) yes
    O4 H4 N1 7_645 0.84 2.01 2.818(3) 160 yes
    C5 H5A O4 . 0.99 2.27 2.705(4) 105 yes
    C65 H65 O4 3_455 0.95 2.43 3.334(4) 158 yes
    C12 H12B Cg1 1_455 0.98 2.89 3.314(4) 107 yes
    C16 H16A Cg2 5_665 0.98 2.65 3.598(4) 162 yes
