##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-2018/3
_journal_date_recd_electronic     2023-06-30
_journal_date_accepted     2023-08-24
_journal_name_full     'IUCrData'
_journal_year     2023
_journal_volume     8
_journal_issue      9
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314623007435
_journal_coeditor_code     BH4077
_publ_contact_author_name     'Manuel Stapf'
_publ_contact_author_address
;
Institut für Organische Chemie
Technische Universität Bergakademie Freiberg
Leipziger Strasse 29
09599 Freiberg
Germany
;
_publ_contact_author_email     manuel.stapf@chemie.tu-freiberg.de
_publ_contact_author_fax       493731393170
_publ_contact_author_phone       493731393580
_publ_section_title
;
N,N'-[1,4-Phenylenebis(iminocarbonyl)]bis(L-phenylalanine)
tetrahydrofuran disolvate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    "Stapf, Manuel" .
;
Institut für Organische Chemie
Technische Universität Bergakademie Freiberg
Leipziger Strasse 29
09599 Freiberg
Germany
;
    "Schwarzer, Anke" .
;
Institut für Organische Chemie
Technische Universität Bergakademie Freiberg
Leipziger Strasse 29
09599 Freiberg
Germany
;
_publ_section_synopsis
;
In the crystal structure of the title bis-urea derivative, the host molecules
are linked by N---H...O=C hydrogen bonds and C---H...O contacts with
R₂¹(6) and R₂¹(7) ring motifs.
;
_chemical_name_systematic
;
N,N'-[1,4-Phenylenebis(iminocarbonyl)]bis(L-phenylalanine)
tetrahydrofuran disolvate
;
_chemical_formula_moiety     'C26 H26 N4 O6, 2(C4 H8 O)'
_chemical_formula_sum     'C34 H42 N4 O8'
_chemical_formula_iupac     'C26 H26 N4 O6, 2C4 H8 O'
_chemical_formula_weight     634.71
_chemical_melting_point     ?
_chemical_absolute_configuration     syn
_space_group_crystal_system     tetragonal
_space_group_name_H-M_alt     'I 41'
_space_group_name_Hall     'I 4bw'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y+1/2, z+1/2'
    '-y, x+1/2, z+1/4'
    'y+1/2, -x, z+3/4'
    'x+1/2, y+1/2, z+1/2'
    '-x+1, -y+1, z+1'
    '-y+1/2, x+1, z+3/4'
    'y+1, -x+1/2, z+5/4'
_cell_length_a     13.632(4)
_cell_length_b     13.632(4)
_cell_length_c     17.507(6)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     3253(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1266
_cell_measurement_theta_min     3.08
_cell_measurement_theta_max     26.66
_cell_measurement_temperature     153(2)
_exptl_crystal_description     chunk
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.100
_exptl_crystal_size_mid     0.050
_exptl_crystal_size_min     0.040
_exptl_crystal_density_diffrn     1.296
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1352
_exptl_absorpt_coefficient_mu     0.093
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     153
_diffrn_source     'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_power     2.000
_diffrn_source_voltage     50
_diffrn_source_current     40
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'plane graphite'
_diffrn_measurement_device_type     'STOE IPDS 2T'
_diffrn_measurement_device     '2-circle goniometer'
_diffrn_measurement_method     'rotation method'
_diffrn_detector     'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     25670
_diffrn_reflns_av_R_equivalents     0.0277
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_theta_min     2.989
_diffrn_reflns_theta_max     26.997
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_refine_special_details     ?
_reflns_number_total     3554
_reflns_number_gt     3269
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0446
_refine_ls_R_factor_gt     0.0395
_refine_ls_wR_factor_gt     0.1014
_refine_ls_wR_factor_ref     0.1067
_refine_ls_goodness_of_fit_ref     1.053
_refine_ls_restrained_S_all     1.108
_refine_ls_number_reflns     3554
_refine_ls_number_parameters     266
_refine_ls_number_restraints     95
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0557P)²+2.0532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.308
_refine_diff_density_min     -0.202
_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' 0.0033 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
;
X-AREA (Stoe & Cie, 2009)
;
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2009)
;
_computing_data_reduction
;
X-RED (Stoe & Cie, 2009)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
XP (Sheldrick, 2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), publCIF (Westrip, 2010)
and
shelXle (Hübschle et al.,  2011)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.38152(16) 0.16933(16) 0.54757(12) 0.0285(4) Uani d 1 . .
    H H1N 0.376(2) 0.194(2) 0.504(2) 0.030(8) Uiso d 1 . .
    N N2 0.27971(16) 0.29428(15) 0.58122(12) 0.0278(4) Uani d 1 . .
    H H2N 0.285(2) 0.310(2) 0.533(2) 0.034(8) Uiso d 1 . .
    O O1 0.31329(14) 0.17368(13) 0.66808(10) 0.0302(4) Uani d 1 . .
    O O2 0.11068(16) 0.19008(15) 0.57508(14) 0.0445(5) Uani d 1 . .
    O O3 0.02642(16) 0.30373(19) 0.63921(15) 0.0529(6) Uani d 1 . .
    H H3O -0.023(4) 0.263(4) 0.627(5) 0.14(3) Uiso d 1 . .
    C C1 0.3225(2) 0.5393(2) 0.54681(18) 0.0389(6) Uani d 1 . .
    H H1 0.302627 0.524528 0.496096 0.047 Uiso calc 1 . .
    C C2 0.4061(2) 0.5960(2) 0.55894(19) 0.0460(7) Uani d 1 . .
    H H2A 0.442763 0.619510 0.516591 0.055 Uiso calc 1 . .
    C C3 0.4360(2) 0.6185(2) 0.6331(2) 0.0497(8) Uani d 1 . .
    H H3 0.493013 0.657049 0.641531 0.060 Uiso calc 1 . .
    C C4 0.3818(3) 0.5840(2) 0.69431(19) 0.0466(7) Uani d 1 . .
    H H4 0.401726 0.599088 0.744967 0.056 Uiso calc 1 . .
    C C5 0.2986(2) 0.5276(2) 0.68217(16) 0.0380(6) Uani d 1 . .
    H H5 0.262005 0.504595 0.724742 0.046 Uiso calc 1 . .
    C C6 0.26774(19) 0.50397(18) 0.60822(16) 0.0313(5) Uani d 1 . .
    C C7 0.17887(19) 0.44008(19) 0.59624(15) 0.0327(6) Uani d 1 . .
    H H7A 0.161232 0.440197 0.541378 0.039 Uiso calc 1 . .
    H H7B 0.122863 0.467660 0.625126 0.039 Uiso calc 1 . .
    C C8 0.19711(18) 0.33349(18) 0.62249(14) 0.0283(5) Uani d 1 . .
    H H8 0.213017 0.333795 0.678256 0.034 Uiso calc 1 . .
    C C9 0.32327(17) 0.20934(17) 0.60329(13) 0.0252(5) Uani d 1 . .
    C C10 0.43982(17) 0.08384(17) 0.55283(14) 0.0250(5) Uani d 1 . .
    C C11 0.47052(18) 0.04159(18) 0.62133(14) 0.0275(5) Uani d 1 . .
    H H11 0.450935 0.069967 0.668486 0.033 Uiso calc 1 . .
    C C12 0.4700(2) 0.0413(2) 0.48385(14) 0.0341(6) Uani d 1 . .
    H H12 0.449394 0.068988 0.436734 0.041 Uiso calc 1 . .
    C C13 0.1072(2) 0.2663(2) 0.60914(15) 0.0370(6) Uani d 1 . .
    O O4A 0.6924(5) 0.1252(4) 0.3577(7) 0.048(2) Uani d 0.571(15) A 1
    C C14A 0.5578(8) 0.2254(9) 0.3317(12) 0.062(5) Uani d 0.571(15) A 1
    H H14A 0.519420 0.224367 0.379670 0.074 Uiso calc 0.571(15) A 1
    H H14B 0.515206 0.247603 0.289262 0.074 Uiso calc 0.571(15) A 1
    C C15A 0.6031(10) 0.1256(10) 0.3148(10) 0.046(4) Uani d 0.571(15) A 1
    H H15A 0.559079 0.071968 0.331644 0.055 Uiso calc 0.571(15) A 1
    H H15B 0.616352 0.118003 0.259558 0.055 Uiso calc 0.571(15) A 1
    C C16A 0.7185(6) 0.2206(5) 0.3801(6) 0.057(2) Uani d 0.571(15) A 1
    H H16A 0.787187 0.234862 0.365513 0.068 Uiso calc 0.571(15) A 1
    H H16B 0.711966 0.228135 0.436102 0.068 Uiso calc 0.571(15) A 1
    C C17A 0.6488(4) 0.2893(4) 0.3391(4) 0.0483(19) Uani d 0.571(15) A 1
    H H17A 0.674677 0.308654 0.288402 0.058 Uiso calc 0.571(15) A 1
    H H17B 0.635496 0.348937 0.369627 0.058 Uiso calc 0.571(15) A 1
    O O4B 0.6865(10) 0.1184(7) 0.3439(12) 0.081(5) Uani d 0.429(15) A 2
    C C14B 0.5595(10) 0.2278(11) 0.3178(12) 0.043(4) Uani d 0.429(15) A 2
    H H14C 0.491571 0.225648 0.337787 0.052 Uiso calc 0.429(15) A 2
    H H14D 0.560401 0.268410 0.270882 0.052 Uiso calc 0.429(15) A 2
    C C15B 0.5969(15) 0.1248(10) 0.3012(13) 0.046(4) Uani d 0.429(15) A 2
    H H15C 0.549184 0.074772 0.318503 0.056 Uiso calc 0.429(15) A 2
    H H15D 0.609168 0.115831 0.245904 0.056 Uiso calc 0.429(15) A 2
    C C16B 0.7256(7) 0.2178(7) 0.3503(8) 0.053(3) Uani d 0.429(15) A 2
    H H16C 0.748952 0.243547 0.300663 0.064 Uiso calc 0.429(15) A 2
    H H16D 0.778608 0.222487 0.388781 0.064 Uiso calc 0.429(15) A 2
    C C17B 0.6294(8) 0.2691(10) 0.3774(10) 0.088(4) Uani d 0.429(15) A 2
    H H17C 0.610777 0.249281 0.429818 0.105 Uiso calc 0.429(15) A 2
    H H17D 0.634210 0.341453 0.374449 0.105 Uiso calc 0.429(15) A 2
_geom_special_details     ?
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
    N1 C9 . 1.371(3) ?
    N1 C10 . 1.413(3) ?
    N1 H1N . 0.84(4) ?
    N2 C9 . 1.357(3) ?
    N2 C8 . 1.441(3) ?
    N2 H2N . 0.88(3) ?
    O1 C9 . 1.241(3) ?
    O2 C13 . 1.199(4) ?
    O3 C13 . 1.324(4) ?
    O3 H3O . 0.90(3) ?
    C1 C2 . 1.393(5) ?
    C1 C6 . 1.395(4) ?
    C1 H1 . 0.9500 ?
    C2 C3 . 1.395(5) ?
    C2 H2A . 0.9500 ?
    C3 C4 . 1.383(5) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.387(4) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.399(4) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.507(4) ?
    C7 C8 . 1.544(3) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 C13 . 1.547(4) ?
    C8 H8 . 1.0000 ?
    C10 C11 . 1.395(3) ?
    C10 C12 . 1.402(3) ?
    C11 C11 6_544 1.390(5) ?
    C11 H11 . 0.9500 ?
    C12 C12 6_544 1.390(5) ?
    C12 H12 . 0.9500 ?
    O4A C16A . 1.405(8) ?
    O4A C15A . 1.430(8) ?
    C14A C15A . 1.522(9) ?
    C14A C17A . 1.522(10) ?
    C14A H14A . 0.9900 ?
    C14A H14B . 0.9900 ?
    C15A H15A . 0.9900 ?
    C15A H15B . 0.9900 ?
    C16A C17A . 1.515(8) ?
    C16A H16A . 0.9900 ?
    C16A H16B . 0.9900 ?
    C17A H17A . 0.9900 ?
    C17A H17B . 0.9900 ?
    O4B C15B . 1.435(10) ?
    O4B C16B . 1.460(10) ?
    C14B C15B . 1.521(9) ?
    C14B C17B . 1.521(11) ?
    C14B H14C . 0.9900 ?
    C14B H14D . 0.9900 ?
    C15B H15C . 0.9900 ?
    C15B H15D . 0.9900 ?
    C16B C17B . 1.560(10) ?
    C16B H16C . 0.9900 ?
    C16B H16D . 0.9900 ?
    C17B H17C . 0.9900 ?
    C17B H17D . 0.9900 ?
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
    C9 N1 C10 . . 127.4(2) ?
    C9 N1 H1N . . 116(2) ?
    C10 N1 H1N . . 116(2) ?
    C9 N2 C8 . . 121.0(2) ?
    C9 N2 H2N . . 117(2) ?
    C8 N2 H2N . . 117(2) ?
    C13 O3 H3O . . 107(5) ?
    C2 C1 C6 . . 120.8(3) ?
    C2 C1 H1 . . 119.6 ?
    C6 C1 H1 . . 119.6 ?
    C1 C2 C3 . . 120.2(3) ?
    C1 C2 H2A . . 119.9 ?
    C3 C2 H2A . . 119.9 ?
    C4 C3 C2 . . 119.4(3) ?
    C4 C3 H3 . . 120.3 ?
    C2 C3 H3 . . 120.3 ?
    C3 C4 C5 . . 120.4(3) ?
    C3 C4 H4 . . 119.8 ?
    C5 C4 H4 . . 119.8 ?
    C4 C5 C6 . . 121.0(3) ?
    C4 C5 H5 . . 119.5 ?
    C6 C5 H5 . . 119.5 ?
    C1 C6 C5 . . 118.2(3) ?
    C1 C6 C7 . . 121.5(3) ?
    C5 C6 C7 . . 120.2(2) ?
    C6 C7 C8 . . 111.9(2) ?
    C6 C7 H7A . . 109.2 ?
    C8 C7 H7A . . 109.2 ?
    C6 C7 H7B . . 109.2 ?
    C8 C7 H7B . . 109.2 ?
    H7A C7 H7B . . 107.9 ?
    N2 C8 C7 . . 109.0(2) ?
    N2 C8 C13 . . 108.9(2) ?
    C7 C8 C13 . . 112.6(2) ?
    N2 C8 H8 . . 108.8 ?
    C7 C8 H8 . . 108.8 ?
    C13 C8 H8 . . 108.8 ?
    O1 C9 N2 . . 123.1(2) ?
    O1 C9 N1 . . 123.9(2) ?
    N2 C9 N1 . . 113.0(2) ?
    C11 C10 C12 . . 118.8(2) ?
    C11 C10 N1 . . 124.4(2) ?
    C12 C10 N1 . . 116.8(2) ?
    C11 C11 C10 6_544 . 120.70(14) ?
    C11 C11 H11 6_544 . 119.7 ?
    C10 C11 H11 . . 119.7 ?
    C12 C12 C10 6_544 . 120.52(15) ?
    C12 C12 H12 6_544 . 119.7 ?
    C10 C12 H12 . . 119.7 ?
    O2 C13 O3 . . 124.4(3) ?
    O2 C13 C8 . . 123.9(3) ?
    O3 C13 C8 . . 111.8(3) ?
    C16A O4A C15A . . 111.0(7) ?
    C15A C14A C17A . . 101.4(8) ?
    C15A C14A H14A . . 111.5 ?
    C17A C14A H14A . . 111.5 ?
    C15A C14A H14B . . 111.5 ?
    C17A C14A H14B . . 111.5 ?
    H14A C14A H14B . . 109.3 ?
    O4A C15A C14A . . 104.3(7) ?
    O4A C15A H15A . . 110.9 ?
    C14A C15A H15A . . 110.9 ?
    O4A C15A H15B . . 110.9 ?
    C14A C15A H15B . . 110.9 ?
    H15A C15A H15B . . 108.9 ?
    O4A C16A C17A . . 106.4(6) ?
    O4A C16A H16A . . 110.5 ?
    C17A C16A H16A . . 110.5 ?
    O4A C16A H16B . . 110.5 ?
    C17A C16A H16B . . 110.5 ?
    H16A C16A H16B . . 108.6 ?
    C16A C17A C14A . . 101.4(6) ?
    C16A C17A H17A . . 111.5 ?
    C14A C17A H17A . . 111.5 ?
    C16A C17A H17B . . 111.5 ?
    C14A C17A H17B . . 111.5 ?
    H17A C17A H17B . . 109.3 ?
    C15B O4B C16B . . 107.1(10) ?
    C15B C14B C17B . . 105.2(7) ?
    C15B C14B H14C . . 110.7 ?
    C17B C14B H14C . . 110.7 ?
    C15B C14B H14D . . 110.7 ?
    C17B C14B H14D . . 110.7 ?
    H14C C14B H14D . . 108.8 ?
    O4B C15B C14B . . 104.0(8) ?
    O4B C15B H15C . . 111.0 ?
    C14B C15B H15C . . 111.0 ?
    O4B C15B H15D . . 111.0 ?
    C14B C15B H15D . . 111.0 ?
    H15C C15B H15D . . 109.0 ?
    O4B C16B C17B . . 97.6(8) ?
    O4B C16B H16C . . 112.2 ?
    C17B C16B H16C . . 112.2 ?
    O4B C16B H16D . . 112.2 ?
    C17B C16B H16D . . 112.2 ?
    H16C C16B H16D . . 109.8 ?
    C14B C17B C16B . . 98.8(10) ?
    C14B C17B H17C . . 112.0 ?
    C16B C17B H17C . . 112.0 ?
    C14B C17B H17D . . 112.0 ?
    C16B C17B H17D . . 112.0 ?
    H17C C17B H17D . . 109.7 ?
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
    C6 C1 C2 C3 . . . . -0.1(5) ?
    C1 C2 C3 C4 . . . . -0.1(5) ?
    C2 C3 C4 C5 . . . . 0.1(5) ?
    C3 C4 C5 C6 . . . . 0.2(5) ?
    C2 C1 C6 C5 . . . . 0.4(4) ?
    C2 C1 C6 C7 . . . . -178.2(3) ?
    C4 C5 C6 C1 . . . . -0.5(4) ?
    C4 C5 C6 C7 . . . . 178.2(3) ?
    C1 C6 C7 C8 . . . . 110.2(3) ?
    C5 C6 C7 C8 . . . . -68.4(3) ?
    C9 N2 C8 C7 . . . . 167.2(2) ?
    C9 N2 C8 C13 . . . . -69.6(3) ?
    C6 C7 C8 N2 . . . . -57.9(3) ?
    C6 C7 C8 C13 . . . . -178.9(2) ?
    C8 N2 C9 O1 . . . . -18.6(4) ?
    C8 N2 C9 N1 . . . . 163.4(2) ?
    C10 N1 C9 O1 . . . . -0.6(4) ?
    C10 N1 C9 N2 . . . . 177.4(2) ?
    C9 N1 C10 C11 . . . . -19.7(4) ?
    C9 N1 C10 C12 . . . . 161.9(2) ?
    C12 C10 C11 C11 . . . 6_544 -0.4(4) ?
    N1 C10 C11 C11 . . . 6_544 -178.7(3) ?
    C11 C10 C12 C12 . . . 6_544 -0.4(5) ?
    N1 C10 C12 C12 . . . 6_544 178.1(3) ?
    N2 C8 C13 O2 . . . . 5.8(4) ?
    C7 C8 C13 O2 . . . . 126.8(3) ?
    N2 C8 C13 O3 . . . . -173.6(2) ?
    C7 C8 C13 O3 . . . . -52.6(3) ?
    C16A O4A C15A C14A . . . . -16.5(18) ?
    C17A C14A C15A O4A . . . . 34.2(17) ?
    C15A O4A C16A C17A . . . . -8.6(15) ?
    O4A C16A C17A C14A . . . . 29.8(13) ?
    C15A C14A C17A C16A . . . . -38.3(15) ?
    C16B O4B C15B C14B . . . . -28(2) ?
    C17B C14B C15B O4B . . . . -6(2) ?
    C15B O4B C16B C17B . . . . 48.8(18) ?
    C15B C14B C17B C16B . . . . 34(2) ?
    O4B C16B C17B C14B . . . . -48.8(16) ?
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 H1N O1 7_544 0.84(4) 2.32(3) 3.091(3) 153(3) yes
    N2 H2N O1 7_544 0.88(3) 2.08(4) 2.937(3) 163(3) yes
    O3 H3O O4A 3_545 0.90(3) 1.73(3) 2.623(7) 175(7) yes
    C5 H5 O2 8_454 0.95 2.55 3.464(4) 160.8 yes
    C8 H8 O2 8_454 1.00 2.70 3.629(4) 155.0 yes
    C11 H11 O1 . 0.95 2.35 2.916(3) 117.8 yes
    C14A H14B O3 2_554 0.99 2.78 3.581(18) 138.8 yes
    C16A H16A <i>Cg</i>1 1_565 0.99 2.61 3.497(8) 149 yes
    C16B H16D <i>Cg</i>1 1_565 0.99 2.82 3.449(10) 122 yes
    C17A H17B <i>Cg</i>2 4_564 0.99 3.00 3.574(8) 117.7 yes
_shelx_space_group_comment     ?
_shelx_estimated_absorpt_T_min     0.991
_shelx_estimated_absorpt_T_max     0.996
