##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'by teXsan'
_journal_date_recd_electronic     2005-11-08
_journal_date_accepted     2005-12-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      1
_journal_page_first     o153
_journal_page_last     o155
_journal_paper_category     EO
_journal_coeditor_code     IS6153
_publ_contact_author_name     'Prof. Ko-Ki Kunimoto'
_publ_contact_author_address
; Division of Material Sciences
  Graduate School of Natural Science and Technology
  Kanazawa University
  Kakuma-machi
  Kanazawa 920-1192
  Japan
;
_publ_contact_author_email     kunimoto@sgkit.ge.kanazawa-u.ac.jp
_publ_contact_author_fax     '81 76 264 6292'
_publ_contact_author_phone     '81 76 264 6292'
_publ_section_title
;
(R)-1-Phenylethylammonium N-tetradecanoyl-L-phenylalaninate
monohydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Ogawa, Toshikazu' .
; Division of Material Sciences
  Graduate School of Natural Science and Technology
  Kanazawa University
  Kakuma-machi
  Kanazawa 920-1192
  Japan
;
    'Ohta, Akio' .
; Division of Material Sciences
  Graduate School of Natural Science and Technology
  Kanazawa University
  Kakuma-machi
  Kanazawa 920-1192
  Japan
;
    'Hata, Yoshitoki' .
; Division of Material Sciences
  Graduate School of Natural Science and Technology
  Kanazawa University
  Kakuma-machi
  Kanazawa 920-1192
  Japan
;
    'Miyagishi, Shigeyoshi' .
; Division of Material Sciences
  Graduate School of Natural Science and Technology
  Kanazawa University
  Kakuma-machi
  Kanazawa 920-1192
  Japan
;
    'Kunimoto, Ko-Ki' .
; Division of Material Sciences
  Graduate School of Natural Science and Technology
  Kanazawa University
  Kakuma-machi
  Kanazawa 920-1192
  Japan
;
data_I
_chemical_name_systematic
;
(R)-1-Phenylethylammonium N-tetradecanoyl-L-phenylalaninate monohydrate
;
_chemical_formula_moiety     'C8 H12 N +, C23 H36 N O3 -, H2 O'
_chemical_formula_sum     'C31 H50 N2 O4 '
_chemical_formula_iupac     'C8 H12 N +, C23 H36 N O3 -, H2 O'
_chemical_formula_weight     514.73
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    '-x,1/2+y,-z'
_cell_length_a     10.920(4)
_cell_length_b     4.9902(17)
_cell_length_c     27.926(10)
_cell_angle_alpha     90
_cell_angle_beta     94.085(8)
_cell_angle_gamma     90
_cell_volume     1517.9(9)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5442
_cell_measurement_theta_min     7.2
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     123.2
_exptl_crystal_description     'Plate'
_exptl_crystal_colour     'Colorless'
_exptl_crystal_size_max     0.500
_exptl_crystal_size_mid     0.200
_exptl_crystal_size_min     0.100
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.126
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     564
_exptl_absorpt_coefficient_mu     0.073
_exptl_absorpt_correction_type     none
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_measurement_device_type     'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     14.63
_diffrn_reflns_number     16351
_diffrn_reflns_av_R_equivalents     0.100
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_theta_full     27.5
_diffrn_measured_fraction_theta_max     0.9677
_diffrn_measured_fraction_theta_full     0.9677
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -35
_diffrn_reflns_limit_l_max     35
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_refine_special_details
;
Refinement using reflections with F² > -10.0 sigma(F²). The weighted
R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are
based on F. The threshold expression of F² > 2.0 sigma(F²) is used only
for calculating R-factor (gt).
;
_reflns_number_total     3774
_reflns_number_gt     2920
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_gt     0.0679
_refine_ls_wR_factor_ref     0.1513
_refine_ls_goodness_of_fit_ref     1.059
_refine_ls_number_reflns     3774
_refine_ls_number_parameters     352
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                  'w = 1/[σ²(Fo²) + (0.0384P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     0.000
_refine_diff_density_max     0.20
_refine_diff_density_min     -0.23
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
    'H' 'H' 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
    'N' 'N' 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
    'O' 'O' 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
_computing_data_collection     'CrystalClear (Rigaku, 2000)'
_computing_cell_refinement     'CrystalClear'
_computing_data_reduction
                         'TEXSAN (Molecular Structure Corporation, 2000)'
_computing_structure_solution     'MITHRIL90 (Gilmore, 1990)'
_computing_structure_refinement     'SHELXL93 (Sheldrick, 1993)'
_computing_molecular_graphics
;
ORTEPIII (Johnson & Burnett, 1996) and
MERCURY (Bruno et al.,  2002)
;
_computing_publication_material     'TEXSAN'
loop_
    _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
    _atom_site_type_symbol
    O1 0.2957(2) 1.0792(7) 0.41845(10) 0.0360(7) Uani d . 1.00 . . O
    O2 0.4593(2) 0.9265(5) 0.38397(8) 0.0217(5) Uani d . 1.00 . . O
    O3 0.3805(2) 1.2925(5) 0.28462(10) 0.0275(6) Uani d . 1.00 . . O
    O4 0.5634(3) 0.5884(6) 0.49885(10) 0.0270(6) Uani d . 1.00 . . O
    N1 0.3314(3) 0.8609(6) 0.29735(10) 0.0196(6) Uani d . 1.00 . . N
    N2 0.4315(3) 0.9376(7) 0.59795(12) 0.0210(6) Uani d . 1.00 . . N
    C1 0.3455(3) 0.9770(7) 0.38413(13) 0.0211(7) Uani d . 1.00 . . C
    C2 0.2615(3) 0.9225(7) 0.33811(12) 0.0187(7) Uani d . 1.00 . . C
    C3 0.1674(3) 0.7025(8) 0.34547(12) 0.0219(7) Uani d . 1.00 . . C
    C4 0.0711(3) 0.6899(8) 0.30375(13) 0.0236(7) Uani d . 1.00 . . C
    C5 -0.0296(3) 0.8655(8) 0.30198(14) 0.0303(9) Uani d . 1.00 . . C
    C6 -0.1155(4) 0.8644(9) 0.26247(16) 0.0360(10) Uani d . 1.00 . . C
    C7 -0.1032(4) 0.6868(10) 0.22508(15) 0.0350(9) Uani d . 1.00 . . C
    C8 -0.0052(4) 0.5129(9) 0.22649(15) 0.0341(9) Uani d . 1.00 . . C
    C9 0.0817(4) 0.5123(8) 0.26557(14) 0.0297(9) Uani d . 1.00 . . C
    C10 0.3875(3) 1.0526(7) 0.27413(13) 0.0216(7) Uani d . 1.00 . . C
    C11 0.4583(3) 0.9621(8) 0.23226(13) 0.0251(8) Uani d . 1.00 . . C
    C12 0.3802(4) 0.8076(8) 0.19401(13) 0.0252(8) Uani d . 1.00 . . C
    C13 0.2637(3) 0.9523(8) 0.17555(12) 0.0236(7) Uani d . 1.00 . . C
    C14 0.1933(4) 0.8035(8) 0.13483(13) 0.0265(8) Uani d . 1.00 . . C
    C15 0.0744(3) 0.9407(8) 0.11627(13) 0.0242(7) Uani d . 1.00 . . C
    C16 0.0052(4) 0.7932(8) 0.07511(13) 0.0275(8) Uani d . 1.00 . . C
    C17 -0.1135(4) 0.9302(8) 0.05686(13) 0.0272(8) Uani d . 1.00 . . C
    C18 -0.1797(4) 0.7899(8) 0.01355(13) 0.0261(8) Uani d . 1.00 . . C
    C19 -0.2992(3) 0.9248(8) -0.00424(13) 0.0250(7) Uani d . 1.00 . . C
    C20 -0.3640(3) 0.7883(8) -0.04777(12) 0.0246(8) Uani d . 1.00 . . C
    C21 -0.4838(3) 0.9219(8) -0.06560(13) 0.0269(8) Uani d . 1.00 . . C
    C22 -0.5478(4) 0.7807(8) -0.10908(13) 0.0307(9) Uani d . 1.00 . . C
    C23 -0.6651(4) 0.9180(9) -0.12842(17) 0.0390(10) Uani d . 1.00 . . C
    C24 0.3100(3) 0.9530(8) 0.61958(13) 0.0212(7) Uani d . 1.00 . . C
    C25 0.2150(3) 0.7917(7) 0.59119(12) 0.0210(7) Uani d . 1.00 . . C
    C26 0.0915(3) 0.8420(8) 0.59840(13) 0.0249(8) Uani d . 1.00 . . C
    C27 -0.0017(3) 0.6921(9) 0.57536(14) 0.0272(8) Uani d . 1.00 . . C
    C28 0.0271(3) 0.4880(8) 0.54484(14) 0.0267(8) Uani d . 1.00 . . C
    C29 0.1480(3) 0.4365(8) 0.53622(14) 0.0258(8) Uani d . 1.00 . . C
    C30 0.2418(3) 0.5884(8) 0.55977(13) 0.0235(8) Uani d . 1.00 . . C
    C31 0.3274(4) 0.8684(9) 0.67217(14) 0.0325(10) Uani d . 1.00 . . C
    H1 0.347(4) 0.681(9) 0.2894(14) 0.0233 Uiso d . 1.00 . . H
    H2 0.2173 1.0789 0.3307 0.0225 Uiso calc . 1.00 . . H
    H3 0.2082 0.5310 0.3483 0.0257 Uiso calc . 1.00 . . H
    H4 0.1280 0.7347 0.3741 0.0257 Uiso calc . 1.00 . . H
    H5 -0.0395 0.9813 0.3278 0.0364 Uiso calc . 1.00 . . H
    H6 -0.1826 0.9860 0.2613 0.0436 Uiso calc . 1.00 . . H
    H7 -0.1627 0.6807 0.1984 0.0422 Uiso calc . 1.00 . . H
    H8 0.0032 0.3871 0.2006 0.0399 Uiso calc . 1.00 . . H
    H9 0.1489 0.3869 0.2661 0.0351 Uiso calc . 1.00 . . H
    H10 0.5236 0.8455 0.2442 0.0301 Uiso calc . 1.00 . . H
    H11 0.4909 1.1120 0.2177 0.0301 Uiso calc . 1.00 . . H
    H12 0.3574 0.6372 0.2073 0.0294 Uiso calc . 1.00 . . H
    H13 0.4282 0.7720 0.1675 0.0294 Uiso calc . 1.00 . . H
    H14 0.2122 0.9670 0.2013 0.0284 Uiso calc . 1.00 . . H
    H15 0.2854 1.1202 0.1644 0.0284 Uiso calc . 1.00 . . H
    H16 0.1736 0.6257 0.1459 0.0314 Uiso calc . 1.00 . . H
    H17 0.2447 0.7838 0.1089 0.0314 Uiso calc . 1.00 . . H
    H18 0.0224 0.9499 0.1420 0.0290 Uiso calc . 1.00 . . H
    H19 0.0937 1.1109 0.1055 0.0290 Uiso calc . 1.00 . . H
    H20 -0.0139 0.6140 0.0859 0.0326 Uiso calc . 1.00 . . H
    H21 0.0570 0.7758 0.0493 0.0326 Uiso calc . 1.00 . . H
    H22 -0.1673 0.9299 0.0822 0.0324 Uiso calc . 1.00 . . H
    H23 -0.0951 1.1043 0.0479 0.0324 Uiso calc . 1.00 . . H
    H24 -0.1975 0.6068 0.0224 0.0314 Uiso calc . 1.00 . . H
    H25 -0.1267 0.7840 -0.0119 0.0314 Uiso calc . 1.00 . . H
    H26 -0.3529 0.9196 0.0211 0.0294 Uiso calc . 1.00 . . H
    H27 -0.2818 1.1002 -0.0126 0.0294 Uiso calc . 1.00 . . H
    H28 -0.3813 0.6038 -0.0393 0.0294 Uiso calc . 1.00 . . H
    H29 -0.3103 0.7848 -0.0730 0.0294 Uiso calc . 1.00 . . H
    H30 -0.5379 0.9176 -0.0404 0.0323 Uiso calc . 1.00 . . H
    H31 -0.4670 1.0973 -0.0743 0.0323 Uiso calc . 1.00 . . H
    H32 -0.5671 0.5990 -0.1000 0.0363 Uiso calc . 1.00 . . H
    H33 -0.4926 0.7711 -0.1339 0.0363 Uiso calc . 1.00 . . H
    H34 -0.7216 0.9199 -0.1041 0.0468 Uiso calc . 1.00 . . H
    H35 -0.7005 0.8160 -0.1552 0.0468 Uiso calc . 1.00 . . H
    H36 -0.6471 1.0909 -0.1382 0.0468 Uiso calc . 1.00 . . H
    H37 0.460(4) 0.773(10) 0.6014(15) 0.0248 Uiso d . 1.00 . . H
    H38 0.480(4) 1.085(9) 0.6111(14) 0.0248 Uiso d . 1.00 . . H
    H39 0.428(4) 0.995(9) 0.5688(16) 0.0248 Uiso d . 1.00 . . H
    H40 0.2842 1.1307 0.6187 0.0255 Uiso calc . 1.00 . . H
    H41 0.0712 0.9779 0.6195 0.0302 Uiso calc . 1.00 . . H
    H42 -0.0850 0.7296 0.5805 0.0326 Uiso calc . 1.00 . . H
    H43 -0.0366 0.3821 0.5296 0.0320 Uiso calc . 1.00 . . H
    H44 0.1672 0.2956 0.5144 0.0308 Uiso calc . 1.00 . . H
    H45 0.3250 0.5465 0.5542 0.0275 Uiso calc . 1.00 . . H
    H46 0.3529 0.6821 0.6740 0.0393 Uiso calc . 1.00 . . H
    H47 0.3885 0.9738 0.6883 0.0393 Uiso calc . 1.00 . . H
    H48 0.2523 0.8840 0.6869 0.0393 Uiso calc . 1.00 . . H
    H49 0.537(4) 0.754(10) 0.4968(15) 0.0274 Uiso d . 1.00 . . H
    H50 0.617(4) 0.593(9) 0.5315(15) 0.0274 Uiso d . 1.00 . . H
_geom_special_details
;
;
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
    O1 C1 . . 1.245(5) ?
    O2 C1 . . 1.268(4) ?
    O3 C10 . . 1.236(4) ?
    O4 H49 . . 0.88(5) ?
    O4 H50 . . 1.05(4) ?
    N1 C2 . . 1.448(4) ?
    N1 C10 . . 1.329(5) ?
    N1 H1 . . 0.94(4) ?
    N2 C24 . . 1.499(5) ?
    N2 H37 . . 0.88(5) ?
    N2 H38 . . 0.96(4) ?
    N2 H39 . . 0.86(4) ?
    C1 C2 . . 1.549(5) ?
    C2 C3 . . 1.528(5) ?
    C2 H2 . . 0.93 ?
    C3 C4 . . 1.514(5) ?
    C3 H3 . . 0.97 ?
    C3 H4 . . 0.95 ?
    C4 C5 . . 1.404(5) ?
    C4 C9 . . 1.398(6) ?
    C5 C6 . . 1.396(6) ?
    C5 H5 . . 0.94 ?
    C6 C7 . . 1.383(6) ?
    C6 H6 . . 0.95 ?
    C7 C8 . . 1.376(6) ?
    C7 H7 . . 0.95 ?
    C8 C9 . . 1.394(6) ?
    C8 H8 . . 0.97 ?
    C9 H9 . . 0.96 ?
    C10 C11 . . 1.516(5) ?
    C11 C12 . . 1.527(5) ?
    C11 H10 . . 0.96 ?
    C11 H11 . . 0.93 ?
    C12 C13 . . 1.521(5) ?
    C12 H12 . . 0.97 ?
    C12 H13 . . 0.95 ?
    C13 C14 . . 1.520(5) ?
    C13 H14 . . 0.95 ?
    C13 H15 . . 0.93 ?
    C14 C15 . . 1.525(5) ?
    C14 H16 . . 0.97 ?
    C14 H17 . . 0.95 ?
    C15 C16 . . 1.520(5) ?
    C15 H18 . . 0.95 ?
    C15 H19 . . 0.93 ?
    C16 C17 . . 1.521(5) ?
    C16 H20 . . 0.97 ?
    C16 H21 . . 0.95 ?
    C17 C18 . . 1.533(5) ?
    C17 H22 . . 0.95 ?
    C17 H23 . . 0.93 ?
    C18 C19 . . 1.520(5) ?
    C18 H24 . . 0.97 ?
    C18 H25 . . 0.95 ?
    C19 C20 . . 1.523(5) ?
    C19 H26 . . 0.95 ?
    C19 H27 . . 0.93 ?
    C20 C21 . . 1.520(5) ?
    C20 H28 . . 0.97 ?
    C20 H29 . . 0.95 ?
    C21 C22 . . 1.529(5) ?
    C21 H30 . . 0.95 ?
    C21 H31 . . 0.93 ?
    C22 C23 . . 1.518(6) ?
    C22 H32 . . 0.97 ?
    C22 H33 . . 0.95 ?
    C23 H34 . . 0.95 ?
    C23 H35 . . 0.96 ?
    C23 H36 . . 0.93 ?
    C24 C25 . . 1.495(5) ?
    C24 C31 . . 1.527(5) ?
    C24 H40 . . 0.93 ?
    C25 C26 . . 1.400(5) ?
    C25 C30 . . 1.386(5) ?
    C26 C27 . . 1.384(5) ?
    C26 H41 . . 0.94 ?
    C27 C28 . . 1.378(6) ?
    C27 H42 . . 0.95 ?
    C28 C29 . . 1.383(5) ?
    C28 H43 . . 0.95 ?
    C29 C30 . . 1.400(5) ?
    C29 H44 . . 0.96 ?
    C30 H45 . . 0.96 ?
    C31 H46 . . 0.97 ?
    C31 H47 . . 0.94 ?
    C31 H48 . . 0.95 ?
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
    O1 O4 2.683(4) . 2_656 ?
    O1 C27 3.276(5) . 2_556 ?
    O1 N2 3.532(4) . 2_656 ?
    O2 N2 2.747(4) . 2_646 ?
    O2 N2 2.845(4) . 2_656 ?
    O2 O4 3.397(4) . 2_656 ?
    O2 C24 3.461(4) . 2_646 ?
    O3 N1 2.913(4) . 1_565 ?
    O3 C31 3.351(5) . 2_656 ?
    O3 C9 3.448(5) . 1_565 ?
    O4 N2 2.810(4) . 2_646 ?
    O4 O4 2.857(4) . 2_656 ?
    O4 O4 2.857(4) . 2_646 ?
    O4 C1 3.393(4) . 2_646 ?
    N2 C1 3.360(5) . 2_646 ?
    C26 C29 3.514(6) . 1_565 ?
    C28 C28 3.555(6) . 2_556 ?
    C28 C28 3.555(6) . 2_546 ?
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
    H49 O4 H50 . . . 101(4) ?
    C2 N1 C10 . . . 121.2(3) ?
    C2 N1 H1 . . . 120(3) ?
    C10 N1 H1 . . . 118(3) ?
    C24 N2 H37 . . . 109(3) ?
    C24 N2 H38 . . . 107(2) ?
    C24 N2 H39 . . . 113(3) ?
    H37 N2 H38 . . . 119(4) ?
    H37 N2 H39 . . . 114(4) ?
    H38 N2 H39 . . . 95(4) ?
    O1 C1 O2 . . . 124.5(3) ?
    O1 C1 C2 . . . 116.5(3) ?
    O2 C1 C2 . . . 119.0(3) ?
    N1 C2 C1 . . . 112.1(3) ?
    N1 C2 C3 . . . 110.5(3) ?
    N1 C2 H2 . . . 107.2 ?
    C1 C2 C3 . . . 112.3(3) ?
    C1 C2 H2 . . . 107.7 ?
    C3 C2 H2 . . . 106.7 ?
    C2 C3 C4 . . . 111.3(3) ?
    C2 C3 H3 . . . 109.7 ?
    C2 C3 H4 . . . 110.0 ?
    C4 C3 H3 . . . 108.6 ?
    C4 C3 H4 . . . 108.9 ?
    H3 C3 H4 . . . 108.4 ?
    C3 C4 C5 . . . 120.0(3) ?
    C3 C4 C9 . . . 121.5(3) ?
    C5 C4 C9 . . . 118.4(3) ?
    C4 C5 C6 . . . 120.4(4) ?
    C4 C5 H5 . . . 119.5 ?
    C6 C5 H5 . . . 120.1 ?
    C5 C6 C7 . . . 120.2(4) ?
    C5 C6 H6 . . . 119.9 ?
    C7 C6 H6 . . . 119.9 ?
    C6 C7 C8 . . . 120.0(4) ?
    C6 C7 H7 . . . 120.8 ?
    C8 C7 H7 . . . 119.2 ?
    C7 C8 C9 . . . 120.5(4) ?
    C7 C8 H8 . . . 120.2 ?
    C9 C8 H8 . . . 119.2 ?
    C4 C9 C8 . . . 120.5(4) ?
    C4 C9 H9 . . . 120.3 ?
    C8 C9 H9 . . . 119.2 ?
    O3 C10 N1 . . . 122.9(3) ?
    O3 C10 C11 . . . 121.0(3) ?
    N1 C10 C11 . . . 116.1(3) ?
    C10 C11 C12 . . . 113.6(3) ?
    C10 C11 H10 . . . 108.6 ?
    C10 C11 H11 . . . 109.2 ?
    C12 C11 H10 . . . 107.5 ?
    C12 C11 H11 . . . 108.1 ?
    H10 C11 H11 . . . 109.8 ?
    C11 C12 C13 . . . 114.1(3) ?
    C11 C12 H12 . . . 108.8 ?
    C11 C12 H13 . . . 109.1 ?
    C13 C12 H12 . . . 108.3 ?
    C13 C12 H13 . . . 108.5 ?
    H12 C12 H13 . . . 107.7 ?
    C12 C13 C14 . . . 112.8(3) ?
    C12 C13 H14 . . . 107.9 ?
    C12 C13 H15 . . . 108.3 ?
    C14 C13 H14 . . . 108.1 ?
    C14 C13 H15 . . . 108.5 ?
    H14 C13 H15 . . . 111.3 ?
    C13 C14 C15 . . . 114.1(3) ?
    C13 C14 H16 . . . 108.7 ?
    C13 C14 H17 . . . 108.9 ?
    C15 C14 H16 . . . 108.5 ?
    C15 C14 H17 . . . 108.8 ?
    H16 C14 H17 . . . 107.7 ?
    C14 C15 C16 . . . 113.9(3) ?
    C14 C15 H18 . . . 107.8 ?
    C14 C15 H19 . . . 108.2 ?
    C16 C15 H18 . . . 107.7 ?
    C16 C15 H19 . . . 108.0 ?
    H18 C15 H19 . . . 111.3 ?
    C15 C16 C17 . . . 113.7(3) ?
    C15 C16 H20 . . . 108.6 ?
    C15 C16 H21 . . . 109.1 ?
    C17 C16 H20 . . . 108.7 ?
    C17 C16 H21 . . . 109.0 ?
    H20 C16 H21 . . . 107.6 ?
    C16 C17 C18 . . . 113.7(3) ?
    C16 C17 H22 . . . 107.8 ?
    C16 C17 H23 . . . 108.3 ?
    C18 C17 H22 . . . 107.8 ?
    C18 C17 H23 . . . 108.3 ?
    H22 C17 H23 . . . 111.0 ?
    C17 C18 C19 . . . 113.7(3) ?
    C17 C18 H24 . . . 108.7 ?
    C17 C18 H25 . . . 109.1 ?
    C19 C18 H24 . . . 108.5 ?
    C19 C18 H25 . . . 108.9 ?
    H24 C18 H25 . . . 107.9 ?
    C18 C19 C20 . . . 113.7(3) ?
    C18 C19 H26 . . . 107.8 ?
    C18 C19 H27 . . . 108.2 ?
    C20 C19 H26 . . . 107.8 ?
    C20 C19 H27 . . . 108.2 ?
    H26 C19 H27 . . . 111.1 ?
    C19 C20 C21 . . . 113.9(3) ?
    C19 C20 H28 . . . 108.5 ?
    C19 C20 H29 . . . 109.0 ?
    C21 C20 H28 . . . 108.5 ?
    C21 C20 H29 . . . 109.1 ?
    H28 C20 H29 . . . 107.7 ?
    C20 C21 C22 . . . 113.1(3) ?
    C20 C21 H30 . . . 108.2 ?
    C20 C21 H31 . . . 108.5 ?
    C22 C21 H30 . . . 107.8 ?
    C22 C21 H31 . . . 108.2 ?
    H30 C21 H31 . . . 111.1 ?
    C21 C22 C23 . . . 113.7(3) ?
    C21 C22 H32 . . . 108.6 ?
    C21 C22 H33 . . . 108.9 ?
    C23 C22 H32 . . . 108.8 ?
    C23 C22 H33 . . . 109.1 ?
    H32 C22 H33 . . . 107.8 ?
    C22 C23 H34 . . . 108.9 ?
    C22 C23 H35 . . . 108.6 ?
    C22 C23 H36 . . . 109.4 ?
    H34 C23 H35 . . . 108.4 ?
    H34 C23 H36 . . . 111.2 ?
    H35 C23 H36 . . . 110.2 ?
    N2 C24 C25 . . . 111.1(3) ?
    N2 C24 C31 . . . 108.7(3) ?
    N2 C24 H40 . . . 108.2 ?
    C25 C24 C31 . . . 113.3(3) ?
    C25 C24 H40 . . . 107.6 ?
    C31 C24 H40 . . . 107.9 ?
    C24 C25 C26 . . . 117.8(3) ?
    C24 C25 C30 . . . 124.1(3) ?
    C26 C25 C30 . . . 118.1(3) ?
    C25 C26 C27 . . . 121.3(4) ?
    C25 C26 H41 . . . 119.6 ?
    C27 C26 H41 . . . 119.0 ?
    C26 C27 C28 . . . 119.6(3) ?
    C26 C27 H42 . . . 120.2 ?
    C28 C27 H42 . . . 120.2 ?
    C27 C28 C29 . . . 120.5(3) ?
    C27 C28 H43 . . . 119.7 ?
    C29 C28 H43 . . . 119.8 ?
    C28 C29 C30 . . . 119.5(4) ?
    C28 C29 H44 . . . 120.0 ?
    C30 C29 H44 . . . 120.5 ?
    C25 C30 C29 . . . 120.9(3) ?
    C25 C30 H45 . . . 120.6 ?
    C29 C30 H45 . . . 118.5 ?
    C24 C31 H46 . . . 109.4 ?
    C24 C31 H47 . . . 110.0 ?
    C24 C31 H48 . . . 110.0 ?
    H46 C31 H47 . . . 108.6 ?
    H46 C31 H48 . . . 108.1 ?
    H47 C31 H48 . . . 110.7 ?
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
    O1 C1 C2 N1 . . . . 167.1(3) ?
    O1 C1 C2 C3 . . . . -67.8(4) ?
    O2 C1 C2 N1 . . . . -10.0(4) ?
    O2 C1 C2 C3 . . . . 115.1(4) ?
    O3 C10 N1 C2 . . . . -2.4(5) ?
    O3 C10 C11 C12 . . . . -121.3(4) ?
    N1 C2 C3 C4 . . . . -65.2(4) ?
    N1 C10 C11 C12 . . . . 56.7(4) ?
    N2 C24 C25 C26 . . . . -162.9(3) ?
    N2 C24 C25 C30 . . . . 19.9(5) ?
    C1 C2 N1 C10 . . . . -76.7(4) ?
    C1 C2 C3 C4 . . . . 168.8(3) ?
    C2 N1 C10 C11 . . . . 179.7(3) ?
    C2 C3 C4 C5 . . . . -82.7(4) ?
    C2 C3 C4 C9 . . . . 95.1(4) ?
    C3 C2 N1 C10 . . . . 157.2(3) ?
    C3 C4 C5 C6 . . . . 176.8(4) ?
    C3 C4 C9 C8 . . . . -177.0(4) ?
    C4 C5 C6 C7 . . . . 1.1(6) ?
    C4 C9 C8 C7 . . . . -0.5(6) ?
    C5 C4 C9 C8 . . . . 0.8(6) ?
    C5 C6 C7 C8 . . . . -0.8(7) ?
    C6 C5 C4 C9 . . . . -1.1(6) ?
    C6 C7 C8 C9 . . . . 0.5(7) ?
    C10 C11 C12 C13 . . . . 52.9(4) ?
    C11 C12 C13 C14 . . . . 175.5(3) ?
    C12 C13 C14 C15 . . . . 178.7(3) ?
    C13 C14 C15 C16 . . . . 179.2(3) ?
    C14 C15 C16 C17 . . . . 179.8(3) ?
    C15 C16 C17 C18 . . . . 176.8(3) ?
    C16 C17 C18 C19 . . . . 179.2(3) ?
    C17 C18 C19 C20 . . . . 179.1(3) ?
    C18 C19 C20 C21 . . . . 179.8(3) ?
    C19 C20 C21 C22 . . . . -179.6(3) ?
    C20 C21 C22 C23 . . . . -177.8(3) ?
    C24 C25 C26 C27 . . . . -176.7(4) ?
    C24 C25 C30 C29 . . . . 176.7(3) ?
    C25 C26 C27 C28 . . . . 0.3(6) ?
    C25 C30 C29 C28 . . . . -0.7(6) ?
    C26 C25 C24 C31 . . . . 74.5(4) ?
    C26 C25 C30 C29 . . . . -0.5(5) ?
    C26 C27 C28 C29 . . . . -1.6(6) ?
    C27 C26 C25 C30 . . . . 0.7(6) ?
    C27 C28 C29 C30 . . . . 1.8(6) ?
    C30 C25 C24 C31 . . . . -102.7(4) ?
    C30 C25 C24 C31 . . . . -102.7(4) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
    O4 H49 O4 . . 2_656 0.88(5) 2.01(5) 2.857(4) 164(4) yes
    O4 H50 O1 . . 2_646 1.05(4) 1.64(4) 2.683(4) 176(4) yes
    N1 H1 O3 . . 1_545 0.94(4) 1.98(4) 2.913(4) 170(4) yes
    N2 H37 O2 . . 2_646 0.88(5) 1.97(5) 2.845(4) 172(3) yes
    N2 H38 O2 . . 2_656 0.96(4) 1.83(4) 2.747(4) 158(4) yes
    N2 H39 O4 . . 2_656 0.86(4) 1.96(4) 2.810(4) 172(4) yes
