##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# 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 journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'from Oxford Diffraction CIF routine and SHELXL-14/6'
_journal_date_recd_electronic     2023-05-25
_journal_date_accepted     2023-08-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2023
_journal_volume     79
_journal_issue      9
_journal_page_first     837
_journal_page_last     841
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989023006837
_journal_coeditor_code     EX2073
_publ_contact_author_name
;
Dr. John F. Gallagher
;
_publ_contact_author_address
;
School of Chemical Sciences,
Dublin City University, Dublin 9, Ireland
;
_publ_contact_author_email     'john.gallagher@dcu.ie'
_publ_contact_author_fax     '353 1 7005503'
_publ_contact_author_phone     '353 1 7005114'
_publ_section_title
;
The unusual (syn-/anti-)₂ conformation of a
dimethoxypyrimidyl-based tennimide
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_address
    'Mocilac, Pavle'
;    School of Chemical Sciences,
     Dublin City University, Dublin 9, Ireland
;
    'Pohl, Fabian'
;    School of Chemical Sciences,
     Dublin City University, Dublin 9, Ireland
     Fakultät für Chemie und Mineralogie,
     Universität Leipzig, Johannisallee 29, 04103 Leipzig,
     Sachsen, Germany
;
    'Gallagher, John F.'
;    School of Chemical Sciences,
     Dublin City University, Dublin 9, Ireland
;
_publ_section_synopsis
;
The tennimide macrocycle (I) resides on a twofold axis and adopts an
alternate (syn/anti)₂ conformation with no inner cavity
(niche), unlike all previously reported (syn)₄ tennimide
conformations. A partial occupancy water molecule (with 0.167 site occupancy)
at hydrogen-bonding distances to two symmetry-related carbonyl O atoms (as
O---H...O=C) resides on the twofold axis in a molecular niche
between two of the pyridine rings. Macrocycle aggregation occurs as
one-dimensional chains along the (010) direction.
;
data_I
_audit_creation_method     SHELXL-2014/6
_chemical_name_systematic
;
3,11,19,27-Tetrakis(4,6-dimethoxypyrimidin-2-yl)-3,11,19,27,33,34,35,36-\
octaazapentacyclo[27.3.1.1^5,9^.1^13,17^.1^21,25^]hexatriaconta-\
1(33),5,7,9(36),13(35),14,16,21(34),22,24,29,31-dodecaen-\
2,4,10,12,18,20,26,28-octone 0.167-hydrate
;
_chemical_name_common     'Dimethoxypyrimidyltennimide'
_chemical_formula_moiety     'C52 H40 N16 O16, 0.167(H2 O)'
_chemical_formula_sum     'C52 H40.33 N16 O16.17'
_chemical_formula_iupac     'C52 H40 N16 O16, 0.167H2 O'
_chemical_formula_weight     1148.02
_chemical_melting_point     ?
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P b c n'
_space_group_name_Hall     '-P 2n 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y+1/2, z+1/2'
    '-x, y, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y-1/2, -z-1/2'
    'x, -y, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     18.8065(10)
_cell_length_b     10.0745(6)
_cell_length_c     28.847(3)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     5465.6(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2330
_cell_measurement_theta_min     2.80
_cell_measurement_theta_max     63.57
_cell_measurement_temperature     294(2)
_exptl_crystal_description     Plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.390
_exptl_crystal_size_mid     0.300
_exptl_crystal_size_min     0.035
_exptl_crystal_density_diffrn     1.395
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     2374.7
_exptl_absorpt_coefficient_mu     0.906
_exptl_absorpt_correction_type     analytical
_exptl_absorpt_process_details
;
(ABSFAC; Clark & Reid, 1998)
;
_exptl_absorpt_correction_T_min     0.778
_exptl_absorpt_correction_T_max     0.973
_diffrn_ambient_temperature     294(2)
_diffrn_source     'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator     'Mirror'
_diffrn_measurement_device_type     'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     14675
_diffrn_reflns_av_R_equivalents     0.0381
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_theta_min     3.064
_diffrn_reflns_theta_max     63.639
_diffrn_reflns_theta_full     61.080
_diffrn_measured_fraction_theta_max     0.986
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     21
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -33
_diffrn_reflns_limit_l_max     30
_diffrn_standards_number     2330
_diffrn_standards_interval_time     60
_diffrn_standards_decay_%     1
_refine_special_details     ?
_reflns_number_total     4439
_reflns_number_gt     3036
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0819
_refine_ls_R_factor_gt     0.0543
_refine_ls_wR_factor_gt     0.1353
_refine_ls_wR_factor_ref     0.1592
_refine_ls_goodness_of_fit_ref     1.034
_refine_ls_restrained_S_all     1.034
_refine_ls_number_reflns     4439
_refine_ls_number_parameters     392
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0686P)²+1.3472P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     geom
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.188
_refine_diff_density_min     -0.178
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.00055(7)
_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
    'C' 'C' 0.0181 0.0091
                         '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' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_structure_solution
;
SHELXT14/6 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL14/6 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020) and Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL14/6 (Sheldrick, 2015b)
;
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
    O O1 -0.05721(12) 0.3212(2) 0.40663(8) 0.0750(6) Uani d 1 . .
    C C1 -0.03715(15) 0.3931(3) 0.37594(10) 0.0543(7) Uani d 1 . .
    N N1 -0.07837(12) 0.4970(2) 0.35800(8) 0.0544(6) Uani d 1 . .
    O O2 -0.06477(11) 0.43970(19) 0.28185(7) 0.0598(5) Uani d 1 . .
    C C2 -0.07302(13) 0.5274(3) 0.30973(10) 0.0504(7) Uani d 1 . .
    O O3 0.22174(11) 0.6319(2) 0.29594(7) 0.0652(6) Uani d 1 . .
    C C3 0.16807(15) 0.6223(3) 0.31815(10) 0.0527(7) Uani d 1 . .
    N N3 0.13350(13) 0.7385(2) 0.33702(8) 0.0548(6) Uani d 1 . .
    O O4 0.11289(15) 0.9585(2) 0.32596(8) 0.0876(8) Uani d 1 . .
    C C4 0.11694(17) 0.8484(3) 0.31003(11) 0.0619(8) Uani d 1 . .
    C C11 0.13402(14) 0.4934(3) 0.33012(10) 0.0499(6) Uani d 1 . .
    N N12 0.06713(11) 0.4984(2) 0.34536(7) 0.0487(5) Uani d 1 . .
    C C13 0.03634(14) 0.3830(3) 0.35609(9) 0.0487(6) Uani d 1 . .
    C C14 0.07002(16) 0.2620(3) 0.35217(11) 0.0621(8) Uani d 1 . .
    H H14 0.0469 0.1839 0.3605 0.074 Uiso calc 1 . .
    C C15 0.13824(17) 0.2597(3) 0.33575(13) 0.0738(10) Uani d 1 . .
    H H15 0.1622 0.1794 0.3324 0.089 Uiso calc 1 . .
    C C16 0.17103(16) 0.3770(3) 0.32431(12) 0.0655(8) Uani d 1 . .
    H H16 0.2173 0.3776 0.3129 0.079 Uiso calc 1 . .
    C C11A -0.13160(16) 0.5612(3) 0.38435(10) 0.0612(8) Uani d 1 . .
    N N12A -0.18786(13) 0.5977(3) 0.36019(9) 0.0684(7) Uani d 1 . .
    C C13A -0.2347(2) 0.6711(4) 0.38399(14) 0.0897(12) Uani d 1 . .
    C C14A -0.2263(2) 0.6991(5) 0.43042(14) 0.1027(14) Uani d 1 . .
    H H14A -0.2600 0.7475 0.4469 0.123 Uiso calc 1 . .
    C C15A -0.1659(2) 0.6523(4) 0.45107(12) 0.0858(11) Uani d 1 . .
    N N16A -0.11615(15) 0.5832(3) 0.42871(9) 0.0714(8) Uani d 1 . .
    O O13A -0.29127(15) 0.7190(4) 0.36166(12) 0.1228(11) Uani d 1 . .
    C C17A -0.2926(3) 0.7082(6) 0.31264(19) 0.1275(18) Uani d 1 . .
    H H17A -0.2552 0.7613 0.2996 0.191 Uiso calc 1 . .
    H H17B -0.3377 0.7387 0.3012 0.191 Uiso calc 1 . .
    H H17C -0.2858 0.6171 0.3039 0.191 Uiso calc 1 . .
    O O15A -0.15514(19) 0.6812(3) 0.49625(9) 0.1107(10) Uani d 1 . .
    C C18A -0.0908(3) 0.6365(5) 0.51825(14) 0.1134(15) Uani d 1 . .
    H H18A -0.0829 0.5449 0.5108 0.170 Uiso calc 1 . .
    H H18B -0.0952 0.6462 0.5512 0.170 Uiso calc 1 . .
    H H18C -0.0515 0.6887 0.5074 0.170 Uiso calc 1 . .
    C C21 -0.07603(14) 0.6707(3) 0.29661(9) 0.0504(7) Uani d 1 . .
    N N22 -0.09433(12) 0.6954(2) 0.25293(8) 0.0502(6) Uani d 1 . .
    C C23 -0.09991(17) 0.8212(3) 0.23984(10) 0.0581(7) Uani d 1 . .
    C C24 -0.0874(2) 0.9276(3) 0.26911(13) 0.0771(10) Uani d 1 . .
    H H24 -0.0937 1.0146 0.2591 0.093 Uiso calc 1 . .
    C C25 -0.0652(2) 0.9002(3) 0.31365(13) 0.0816(11) Uani d 1 . .
    H H25 -0.0547 0.9689 0.3341 0.098 Uiso calc 1 . .
    C C26 -0.05880(17) 0.7711(3) 0.32738(11) 0.0670(8) Uani d 1 . .
    H H26 -0.0430 0.7508 0.3571 0.080 Uiso calc 1 . .
    C C21A 0.12724(17) 0.7424(3) 0.38590(10) 0.0580(8) Uani d 1 . .
    N N22A 0.07257(14) 0.8089(2) 0.40337(9) 0.0644(7) Uani d 1 . .
    C C23A 0.06838(19) 0.8052(3) 0.44966(11) 0.0704(9) Uani d 1 . .
    C C24A 0.1147(2) 0.7351(3) 0.47695(12) 0.0773(10) Uani d 1 . .
    H H24A 0.1097 0.7312 0.5090 0.093 Uiso calc 1 . .
    C C25A 0.1687(2) 0.6709(3) 0.45415(12) 0.0705(9) Uani d 1 . .
    N N26A 0.17692(14) 0.6744(2) 0.40795(9) 0.0630(7) Uani d 1 . .
    O O23A 0.01530(15) 0.8719(2) 0.47037(8) 0.0903(8) Uani d 1 . .
    C C27A -0.0336(2) 0.9460(4) 0.44195(14) 0.1050(14) Uani d 1 . .
    H H27A -0.0076 1.0071 0.4228 0.158 Uiso calc 1 . .
    H H27B -0.0659 0.9944 0.4614 0.158 Uiso calc 1 . .
    H H27C -0.0599 0.8860 0.4226 0.158 Uiso calc 1 . .
    O O25A 0.21549(15) 0.6015(3) 0.47933(8) 0.0899(8) Uani d 1 . .
    C C28A 0.2726(2) 0.5372(5) 0.45500(16) 0.1113(15) Uani d 1 . .
    H H28A 0.2535 0.4717 0.4343 0.167 Uiso calc 1 . .
    H H28B 0.3037 0.4950 0.4769 0.167 Uiso calc 1 . .
    H H28C 0.2988 0.6019 0.4376 0.167 Uiso calc 1 . .
    O O1W 0.0000 0.187(3) 0.2500 0.180(15) Uani d 0.167 . .
    H H1W -0.0358(4) 0.238(3) 0.248(3) 0.100 Uiso d 0.167 . .
_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
    O1 C1 . 1.205(3) ?
    C1 N1 . 1.402(3) ?
    C1 C13 . 1.499(4) ?
    N1 C11A . 1.414(3) ?
    N1 C2 . 1.429(3) ?
    O2 C2 . 1.205(3) ?
    C2 C21 . 1.494(4) ?
    O3 C3 . 1.200(3) ?
    C3 N3 . 1.446(4) ?
    C3 C11 . 1.488(4) ?
    N3 C4 . 1.389(4) ?
    N3 C21A . 1.416(4) ?
    O4 C4 . 1.203(3) ?
    C4 C23 3 1.499(4) ?
    C11 N12 . 1.333(3) ?
    C11 C16 . 1.374(4) ?
    N12 C13 . 1.335(3) ?
    C13 C14 . 1.378(4) ?
    C14 C15 . 1.368(4) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.373(4) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C11A N12A . 1.319(4) ?
    C11A N16A . 1.331(4) ?
    N12A C13A . 1.339(4) ?
    C13A O13A . 1.334(4) ?
    C13A C14A . 1.378(5) ?
    C14A C15A . 1.367(5) ?
    C14A H14A . 0.9300 ?
    C15A N16A . 1.332(4) ?
    C15A O15A . 1.351(4) ?
    O13A C17A . 1.418(5) ?
    C17A H17A . 0.9600 ?
    C17A H17B . 0.9600 ?
    C17A H17C . 0.9600 ?
    O15A C18A . 1.438(5) ?
    C18A H18A . 0.9600 ?
    C18A H18B . 0.9600 ?
    C18A H18C . 0.9600 ?
    C21 N22 . 1.330(3) ?
    C21 C26 . 1.384(4) ?
    N22 C23 . 1.327(3) ?
    C23 C24 . 1.385(4) ?
    C23 C4 3 1.499(4) ?
    C24 C25 . 1.379(5) ?
    C24 H24 . 0.9300 ?
    C25 C26 . 1.365(5) ?
    C25 H25 . 0.9300 ?
    C26 H26 . 0.9300 ?
    C21A N26A . 1.322(4) ?
    C21A N22A . 1.326(4) ?
    N22A C23A . 1.338(4) ?
    C23A O23A . 1.343(4) ?
    C23A C24A . 1.370(5) ?
    C24A C25A . 1.373(5) ?
    C24A H24A . 0.9300 ?
    C25A O25A . 1.338(4) ?
    C25A N26A . 1.342(4) ?
    O23A C27A . 1.441(4) ?
    C27A H27A . 0.9600 ?
    C27A H27B . 0.9600 ?
    C27A H27C . 0.9600 ?
    O25A C28A . 1.438(5) ?
    C28A H28A . 0.9600 ?
    C28A H28B . 0.9600 ?
    C28A H28C . 0.9600 ?
    O1W H1W . 0.850(5) ?
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
    O1 C1 N1 . . 123.2(3) ?
    O1 C1 C13 . . 121.9(3) ?
    N1 C1 C13 . . 114.8(2) ?
    C1 N1 C11A . . 122.3(2) ?
    C1 N1 C2 . . 118.7(2) ?
    C11A N1 C2 . . 118.4(2) ?
    O2 C2 N1 . . 120.1(3) ?
    O2 C2 C21 . . 123.0(3) ?
    N1 C2 C21 . . 116.8(2) ?
    O3 C3 N3 . . 120.9(3) ?
    O3 C3 C11 . . 123.8(3) ?
    N3 C3 C11 . . 115.2(3) ?
    C4 N3 C21A . . 121.2(2) ?
    C4 N3 C3 . . 122.4(2) ?
    C21A N3 C3 . . 115.8(2) ?
    O4 C4 N3 . . 122.3(3) ?
    O4 C4 C23 . 3 121.4(3) ?
    N3 C4 C23 . 3 116.1(2) ?
    N12 C11 C16 . . 123.4(3) ?
    N12 C11 C3 . . 116.7(2) ?
    C16 C11 C3 . . 119.9(3) ?
    C11 N12 C13 . . 116.9(2) ?
    N12 C13 C14 . . 123.5(3) ?
    N12 C13 C1 . . 115.4(2) ?
    C14 C13 C1 . . 121.0(3) ?
    C15 C14 C13 . . 118.4(3) ?
    C15 C14 H14 . . 120.8 ?
    C13 C14 H14 . . 120.8 ?
    C14 C15 C16 . . 119.3(3) ?
    C14 C15 H15 . . 120.4 ?
    C16 C15 H15 . . 120.4 ?
    C15 C16 C11 . . 118.5(3) ?
    C15 C16 H16 . . 120.7 ?
    C11 C16 H16 . . 120.7 ?
    N12A C11A N16A . . 129.5(3) ?
    N12A C11A N1 . . 114.3(3) ?
    N16A C11A N1 . . 116.0(3) ?
    C11A N12A C13A . . 114.2(3) ?
    O13A C13A N12A . . 118.5(4) ?
    O13A C13A C14A . . 119.1(3) ?
    N12A C13A C14A . . 122.4(4) ?
    C15A C14A C13A . . 116.6(3) ?
    C15A C14A H14A . . 121.7 ?
    C13A C14A H14A . . 121.7 ?
    N16A C15A O15A . . 118.3(4) ?
    N16A C15A C14A . . 123.6(3) ?
    O15A C15A C14A . . 118.1(3) ?
    C11A N16A C15A . . 113.5(3) ?
    C13A O13A C17A . . 117.9(3) ?
    O13A C17A H17A . . 109.5 ?
    O13A C17A H17B . . 109.5 ?
    H17A C17A H17B . . 109.5 ?
    O13A C17A H17C . . 109.5 ?
    H17A C17A H17C . . 109.5 ?
    H17B C17A H17C . . 109.5 ?
    C15A O15A C18A . . 119.0(3) ?
    O15A C18A H18A . . 109.5 ?
    O15A C18A H18B . . 109.5 ?
    H18A C18A H18B . . 109.5 ?
    O15A C18A H18C . . 109.5 ?
    H18A C18A H18C . . 109.5 ?
    H18B C18A H18C . . 109.5 ?
    N22 C21 C26 . . 122.1(3) ?
    N22 C21 C2 . . 115.5(2) ?
    C26 C21 C2 . . 122.3(3) ?
    C23 N22 C21 . . 117.9(2) ?
    N22 C23 C24 . . 123.6(3) ?
    N22 C23 C4 . 3 117.7(2) ?
    C24 C23 C4 . 3 118.7(3) ?
    C25 C24 C23 . . 117.7(3) ?
    C25 C24 H24 . . 121.2 ?
    C23 C24 H24 . . 121.2 ?
    C26 C25 C24 . . 119.2(3) ?
    C26 C25 H25 . . 120.4 ?
    C24 C25 H25 . . 120.4 ?
    C25 C26 C21 . . 119.3(3) ?
    C25 C26 H26 . . 120.3 ?
    C21 C26 H26 . . 120.3 ?
    N26A C21A N22A . . 128.8(3) ?
    N26A C21A N3 . . 114.0(3) ?
    N22A C21A N3 . . 117.2(3) ?
    C21A N22A C23A . . 114.3(3) ?
    N22A C23A O23A . . 118.3(3) ?
    N22A C23A C24A . . 123.4(3) ?
    O23A C23A C24A . . 118.3(3) ?
    C23A C24A C25A . . 116.0(3) ?
    C23A C24A H24A . . 122.0 ?
    C25A C24A H24A . . 122.0 ?
    O25A C25A N26A . . 118.5(3) ?
    O25A C25A C24A . . 118.2(3) ?
    N26A C25A C24A . . 123.3(3) ?
    C21A N26A C25A . . 114.2(3) ?
    C23A O23A C27A . . 118.7(3) ?
    O23A C27A H27A . . 109.5 ?
    O23A C27A H27B . . 109.5 ?
    H27A C27A H27B . . 109.5 ?
    O23A C27A H27C . . 109.5 ?
    H27A C27A H27C . . 109.5 ?
    H27B C27A H27C . . 109.5 ?
    C25A O25A C28A . . 117.5(3) ?
    O25A C28A H28A . . 109.5 ?
    O25A C28A H28B . . 109.5 ?
    H28A C28A H28B . . 109.5 ?
    O25A C28A H28C . . 109.5 ?
    H28A C28A H28C . . 109.5 ?
    H28B C28A H28C . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 N1 C11A . . . . 26.2(4) ?
    C13 C1 N1 C11A . . . . -150.1(3) ?
    O1 C1 N1 C2 . . . . -145.4(3) ?
    C13 C1 N1 C2 . . . . 38.4(3) ?
    C1 N1 C2 O2 . . . . 35.9(4) ?
    C11A N1 C2 O2 . . . . -136.0(3) ?
    C1 N1 C2 C21 . . . . -142.4(3) ?
    C11A N1 C2 C21 . . . . 45.7(3) ?
    O3 C3 N3 C4 . . . . 51.6(4) ?
    C11 C3 N3 C4 . . . . -131.0(3) ?
    O3 C3 N3 C21A . . . . -119.2(3) ?
    C11 C3 N3 C21A . . . . 58.3(3) ?
    C21A N3 C4 O4 . . . . 17.8(5) ?
    C3 N3 C4 O4 . . . . -152.5(3) ?
    C21A N3 C4 C23 . . . 3 -158.6(3) ?
    C3 N3 C4 C23 . . . 3 31.1(4) ?
    O3 C3 C11 N12 . . . . -165.0(3) ?
    N3 C3 C11 N12 . . . . 17.6(4) ?
    O3 C3 C11 C16 . . . . 13.7(4) ?
    N3 C3 C11 C16 . . . . -163.7(3) ?
    C16 C11 N12 C13 . . . . 1.3(4) ?
    C3 C11 N12 C13 . . . . 179.9(2) ?
    C11 N12 C13 C14 . . . . 0.0(4) ?
    C11 N12 C13 C1 . . . . 176.3(2) ?
    O1 C1 C13 N12 . . . . -141.8(3) ?
    N1 C1 C13 N12 . . . . 34.4(3) ?
    O1 C1 C13 C14 . . . . 34.5(4) ?
    N1 C1 C13 C14 . . . . -149.2(3) ?
    N12 C13 C14 C15 . . . . -1.1(5) ?
    C1 C13 C14 C15 . . . . -177.1(3) ?
    C13 C14 C15 C16 . . . . 0.8(5) ?
    C14 C15 C16 C11 . . . . 0.4(5) ?
    N12 C11 C16 C15 . . . . -1.5(5) ?
    C3 C11 C16 C15 . . . . 179.9(3) ?
    C1 N1 C11A N12A . . . . -144.5(3) ?
    C2 N1 C11A N12A . . . . 27.1(4) ?
    C1 N1 C11A N16A . . . . 39.5(4) ?
    C2 N1 C11A N16A . . . . -148.9(3) ?
    N16A C11A N12A C13A . . . . 2.3(5) ?
    N1 C11A N12A C13A . . . . -173.1(3) ?
    C11A N12A C13A O13A . . . . 176.2(4) ?
    C11A N12A C13A C14A . . . . -3.5(6) ?
    O13A C13A C14A C15A . . . . -177.3(4) ?
    N12A C13A C14A C15A . . . . 2.3(7) ?
    C13A C14A C15A N16A . . . . 0.4(7) ?
    C13A C14A C15A O15A . . . . 178.3(4) ?
    N12A C11A N16A C15A . . . . 0.1(5) ?
    N1 C11A N16A C15A . . . . 175.5(3) ?
    O15A C15A N16A C11A . . . . -179.4(3) ?
    C14A C15A N16A C11A . . . . -1.5(6) ?
    N12A C13A O13A C17A . . . . -10.2(6) ?
    C14A C13A O13A C17A . . . . 169.5(5) ?
    N16A C15A O15A C18A . . . . 0.0(6) ?
    C14A C15A O15A C18A . . . . -178.0(4) ?
    O2 C2 C21 N22 . . . . 23.0(4) ?
    N1 C2 C21 N22 . . . . -158.8(2) ?
    O2 C2 C21 C26 . . . . -155.0(3) ?
    N1 C2 C21 C26 . . . . 23.2(4) ?
    C26 C21 N22 C23 . . . . -3.9(4) ?
    C2 C21 N22 C23 . . . . 178.0(2) ?
    C21 N22 C23 C24 . . . . 0.3(5) ?
    C21 N22 C23 C4 . . . 3 177.0(3) ?
    N22 C23 C24 C25 . . . . 2.7(5) ?
    C4 C23 C24 C25 3 . . . -174.0(3) ?
    C23 C24 C25 C26 . . . . -2.1(6) ?
    C24 C25 C26 C21 . . . . -1.3(5) ?
    N22 C21 C26 C25 . . . . 4.5(5) ?
    C2 C21 C26 C25 . . . . -177.6(3) ?
    C4 N3 C21A N26A . . . . -143.9(3) ?
    C3 N3 C21A N26A . . . . 27.0(3) ?
    C4 N3 C21A N22A . . . . 38.0(4) ?
    C3 N3 C21A N22A . . . . -151.2(2) ?
    N26A C21A N22A C23A . . . . 0.1(4) ?
    N3 C21A N22A C23A . . . . 178.0(3) ?
    C21A N22A C23A O23A . . . . 178.8(3) ?
    C21A N22A C23A C24A . . . . -2.4(5) ?
    N22A C23A C24A C25A . . . . 2.4(5) ?
    O23A C23A C24A C25A . . . . -178.8(3) ?
    C23A C24A C25A O25A . . . . 179.7(3) ?
    C23A C24A C25A N26A . . . . -0.3(5) ?
    N22A C21A N26A C25A . . . . 1.8(4) ?
    N3 C21A N26A C25A . . . . -176.1(2) ?
    O25A C25A N26A C21A . . . . 178.3(3) ?
    C24A C25A N26A C21A . . . . -1.7(5) ?
    N22A C23A O23A C27A . . . . -1.2(5) ?
    C24A C23A O23A C27A . . . . 179.9(3) ?
    N26A C25A O25A C28A . . . . 1.3(5) ?
    C24A C25A O25A C28A . . . . -178.7(3) ?
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
    C15 H15 O3 8_655 0.93 2.47 3.148(4) 130 yes
    C15 H15 O4 1_545 0.93 2.42 3.084(4) 129 yes
    C18A H18C O23A . 0.96 2.47 3.393(6) 160 yes
    C24 H24 O1W 1_565 0.93 2.49 3.14(2) 127 yes
    C26 H26 N22A . 0.93 2.62 3.325(4) 133 yes
    C27A H27B O23A 5_576 0.96 2.57 3.144(4) 119 yes
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.719
_shelx_estimated_absorpt_T_max     0.969
_shelxl_version_number     2014/6
