##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_data_validation_number     ?
_journal_date_recd_electronic     2009-06-13
_journal_date_accepted     2009-06-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      7
_journal_page_first     o1657
_journal_page_last     o1657
_journal_paper_category     QO
_journal_coeditor_code     HG2527
_publ_contact_author_name     'Wen-Kui Dong'
_publ_contact_author_address
;
 School of Chemical and Biological Engineering
 Lanzhou Jiaotong University
 Lanzhou 730070
 People's Republic of China
;
_publ_contact_author_email     dongwk@mail.lzjtu.cn
_publ_contact_author_fax     '+86 931 4956512'
_publ_contact_author_phone     '+86 931 4938703'
_publ_section_title
;
2,2'-[1,1'-(Propane-1,3-diyldioxydinitrilo)diethylidyne]di-1-naphthol
;
loop_
    _publ_author_name
    _publ_author_address
    'Wen-Kui Dong'
;
 School of Chemical and Biological Engineering
 Lanzhou Jiaotong University
 Lanzhou 730070
 People's Republic of China
;
    'Jian-Chao Wu'
;
 School of Chemical and Biological Engineering
 Lanzhou Jiaotong University
 Lanzhou 730070
 People's Republic of China
;
    'Yin-Xia Sun'
;
 School of Chemical and Biological Engineering
 Lanzhou Jiaotong University
 Lanzhou 730070
 People's Republic of China
;
    'Li Li'
;
 School of Chemical and Biological Engineering
 Lanzhou Jiaotong University
 Lanzhou 730070
 People's Republic of China
;
    'Jian Yao'
;
 School of Chemical and Biological Engineering
 Lanzhou Jiaotong University
 Lanzhou 730070
 People's Republic of China
;
data_I
_chemical_name_systematic
;
2,2'-[1,1'-(Propane-1,3-diyldioxydinitrilo)diethylidyne]di-1-naphthol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C27 H26 N2 O4'
_chemical_formula_sum     'C27 H26 N2 O4'
_chemical_formula_iupac     'C27 H26 N2 O4'
_chemical_formula_weight     442.50
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.4411(10)
_cell_length_b     8.8911(16)
_cell_length_c     18.106(2)
_cell_angle_alpha     100.6450(10)
_cell_angle_beta     94.3310(10)
_cell_angle_gamma     106.329(2)
_cell_volume     1119.4(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1962
_cell_measurement_theta_min     2.31
_cell_measurement_theta_max     26.265
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block-like
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.42
_exptl_crystal_size_min     0.37
_exptl_crystal_density_diffrn     1.313
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     468
_exptl_absorpt_coefficient_mu     0.089
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9570
_exptl_absorpt_correction_T_max     0.9680
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Siemens SMART 1000 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5800
_diffrn_reflns_av_R_equivalents     0.0247
_diffrn_reflns_av_sigmaI/netI     0.0488
_diffrn_reflns_theta_min     2.31
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.982
_diffrn_measured_fraction_theta_full     0.982
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
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     3876
_reflns_number_gt     2325
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0886
_refine_ls_R_factor_gt     0.0470
_refine_ls_wR_factor_gt     0.1119
_refine_ls_wR_factor_ref     0.1452
_refine_ls_goodness_of_fit_ref     1.040
_refine_ls_restrained_S_all     1.040
_refine_ls_number_reflns     3876
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0669P)²+0.1652P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.219
_refine_diff_density_min     -0.216
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Siemens, 1996)'
_computing_cell_refinement     'SAINT (Siemens, 1996)'
_computing_data_reduction     'SAINT (Siemens, 1996)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.4304(3) 0.3291(2) 0.39356(10) 0.0472(5) Uani d . 1 . .
    N N2 0.5352(3) 0.4359(2) 0.09736(10) 0.0490(5) Uani d . 1 . .
    O O1 0.3227(2) 0.35088(19) 0.33130(9) 0.0531(5) Uani d . 1 . .
    O O2 0.6102(2) 0.55995(19) 0.16190(9) 0.0568(5) Uani d . 1 . .
    O O3 0.7381(2) 0.38979(19) 0.48069(9) 0.0567(5) Uani d . 1 . .
    H H3 0.6693 0.3990 0.4453 0.085 Uiso calc R 1 . .
    O O4 0.2690(2) 0.2606(2) -0.00541(9) 0.0589(5) Uani d . 1 . .
    H H4 0.3176 0.3292 0.0332 0.088 Uiso calc R 1 . .
    C C1 0.4460(3) 0.4646(3) 0.29743(12) 0.0444(6) Uani d . 1 . .
    H H1A 0.5504 0.4264 0.2822 0.053 Uiso calc R 1 . .
    H H1B 0.4971 0.5663 0.3336 0.053 Uiso calc R 1 . .
    C C2 0.3361(3) 0.4864(3) 0.22958(12) 0.0494(6) Uani d . 1 . .
    H H2A 0.2300 0.5216 0.2451 0.059 Uiso calc R 1 . .
    H H2B 0.2864 0.3843 0.1936 0.059 Uiso calc R 1 . .
    C C3 0.4578(4) 0.6083(3) 0.19140(13) 0.0557(7) Uani d . 1 . .
    H H3A 0.3795 0.6253 0.1503 0.067 Uiso calc R 1 . .
    H H3B 0.5088 0.7097 0.2278 0.067 Uiso calc R 1 . .
    C C4 0.1200(3) 0.1930(3) 0.42415(14) 0.0608(7) Uani d . 1 . .
    H H4A 0.0746 0.2444 0.3878 0.091 Uiso calc R 1 . .
    H H4B 0.0718 0.2184 0.4710 0.091 Uiso calc R 1 . .
    H H4C 0.0779 0.0789 0.4052 0.091 Uiso calc R 1 . .
    C C5 0.3322(3) 0.2511(2) 0.43736(12) 0.0421(5) Uani d . 1 . .
    C C6 0.6336(3) 0.2932(2) 0.52118(12) 0.0409(5) Uani d . 1 . .
    C C7 0.4391(3) 0.2236(2) 0.50250(11) 0.0385(5) Uani d . 1 . .
    C C8 0.3456(3) 0.1201(3) 0.54803(13) 0.0488(6) Uani d . 1 . .
    H H8 0.2156 0.0725 0.5366 0.059 Uiso calc R 1 . .
    C C9 0.4393(4) 0.0885(3) 0.60760(13) 0.0510(6) Uani d . 1 . .
    H H9 0.3730 0.0189 0.6356 0.061 Uiso calc R 1 . .
    C C10 0.6365(3) 0.1598(3) 0.62776(12) 0.0445(6) Uani d . 1 . .
    C C11 0.7339(3) 0.2654(2) 0.58449(12) 0.0413(5) Uani d . 1 . .
    C C12 0.9311(3) 0.3417(3) 0.60585(14) 0.0552(7) Uani d . 1 . .
    H H12 0.9972 0.4118 0.5781 0.066 Uiso calc R 1 . .
    C C13 1.0230(4) 0.3126(3) 0.66666(16) 0.0673(8) Uani d . 1 . .
    H H13 1.1520 0.3636 0.6803 0.081 Uiso calc R 1 . .
    C C14 0.9279(4) 0.2076(3) 0.70901(16) 0.0667(8) Uani d . 1 . .
    H H14 0.9933 0.1888 0.7504 0.080 Uiso calc R 1 . .
    C C15 0.7397(4) 0.1326(3) 0.69001(14) 0.0585(7) Uani d . 1 . .
    H H15 0.6777 0.0621 0.7185 0.070 Uiso calc R 1 . .
    C C16 0.8658(4) 0.4430(3) 0.09754(15) 0.0681(8) Uani d . 1 . .
    H H16A 0.8829 0.5187 0.1447 0.102 Uiso calc R 1 . .
    H H16B 0.9350 0.4952 0.0620 0.102 Uiso calc R 1 . .
    H H16C 0.9112 0.3557 0.1058 0.102 Uiso calc R 1 . .
    C C17 0.6600(3) 0.3798(3) 0.06659(12) 0.0449(6) Uani d . 1 . .
    C C18 0.4008(3) 0.1992(3) -0.03454(12) 0.0419(5) Uani d . 1 . .
    C C19 0.5894(3) 0.2506(3) -0.00192(12) 0.0419(5) Uani d . 1 . .
    C C20 0.7126(3) 0.1727(3) -0.03704(14) 0.0518(6) Uani d . 1 . .
    H H20 0.8390 0.2047 -0.0161 0.062 Uiso calc R 1 . .
    C C21 0.6529(3) 0.0533(3) -0.10000(14) 0.0552(6) Uani d . 1 . .
    H H21 0.7382 0.0044 -0.1209 0.066 Uiso calc R 1 . .
    C C22 0.4635(3) 0.0022(3) -0.13423(13) 0.0460(6) Uani d . 1 . .
    C C23 0.3358(3) 0.0756(3) -0.10137(12) 0.0422(5) Uani d . 1 . .
    C C24 0.1464(4) 0.0254(3) -0.13600(14) 0.0582(7) Uani d . 1 . .
    H H24 0.0612 0.0739 -0.1147 0.070 Uiso calc R 1 . .
    C C25 0.0862(4) -0.0921(3) -0.19974(16) 0.0677(8) Uani d . 1 . .
    H H25 -0.0393 -0.1237 -0.2217 0.081 Uiso calc R 1 . .
    C C26 0.2131(4) -0.1659(3) -0.23247(15) 0.0669(8) Uani d . 1 . .
    H H26 0.1715 -0.2467 -0.2761 0.080 Uiso calc R 1 . .
    C C27 0.3962(4) -0.1200(3) -0.20072(14) 0.0604(7) Uani d . 1 . .
    H H27 0.4792 -0.1697 -0.2231 0.072 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    N1 C5 . 1.284(3) ?
    N1 O1 . 1.408(2) ?
    N2 C17 . 1.287(3) ?
    N2 O2 . 1.404(2) ?
    O1 C1 . 1.426(2) ?
    O2 C3 . 1.427(3) ?
    O3 C6 . 1.350(2) ?
    O3 H3 . 0.8200 ?
    O4 C18 . 1.345(3) ?
    O4 H4 . 0.8200 ?
    C1 C2 . 1.497(3) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 C3 . 1.514(3) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 C5 . 1.502(3) ?
    C4 H4A . 0.9600 ?
    C4 H4B . 0.9600 ?
    C4 H4C . 0.9600 ?
    C5 C7 . 1.469(3) ?
    C6 C7 . 1.392(3) ?
    C6 C11 . 1.418(3) ?
    C7 C8 . 1.420(3) ?
    C8 C9 . 1.356(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.414(3) ?
    C9 H9 . 0.9300 ?
    C10 C15 . 1.412(3) ?
    C10 C11 . 1.413(3) ?
    C11 C12 . 1.422(3) ?
    C12 C13 . 1.356(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.391(4) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.357(4) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.498(3) ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    C17 C19 . 1.473(3) ?
    C18 C19 . 1.393(3) ?
    C18 C23 . 1.424(3) ?
    C19 C20 . 1.417(3) ?
    C20 C21 . 1.355(3) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.408(3) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.405(3) ?
    C22 C27 . 1.414(3) ?
    C23 C24 . 1.410(3) ?
    C24 C25 . 1.356(3) ?
    C24 H24 . 0.9300 ?
    C25 C26 . 1.401(4) ?
    C25 H25 . 0.9300 ?
    C26 C27 . 1.355(4) ?
    C26 H26 . 0.9300 ?
    C27 H27 . 0.9300 ?
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
    C5 N1 O1 . . 114.40(18) ?
    C17 N2 O2 . . 113.84(19) ?
    N1 O1 C1 . . 107.51(15) ?
    N2 O2 C3 . . 108.21(17) ?
    C6 O3 H3 . . 109.5 ?
    C18 O4 H4 . . 109.5 ?
    O1 C1 C2 . . 108.60(18) ?
    O1 C1 H1A . . 110.0 ?
    C2 C1 H1A . . 110.0 ?
    O1 C1 H1B . . 110.0 ?
    C2 C1 H1B . . 110.0 ?
    H1A C1 H1B . . 108.4 ?
    C1 C2 C3 . . 111.5(2) ?
    C1 C2 H2A . . 109.3 ?
    C3 C2 H2A . . 109.3 ?
    C1 C2 H2B . . 109.3 ?
    C3 C2 H2B . . 109.3 ?
    H2A C2 H2B . . 108.0 ?
    O2 C3 C2 . . 112.91(19) ?
    O2 C3 H3A . . 109.0 ?
    C2 C3 H3A . . 109.0 ?
    O2 C3 H3B . . 109.0 ?
    C2 C3 H3B . . 109.0 ?
    H3A C3 H3B . . 107.8 ?
    C5 C4 H4A . . 109.5 ?
    C5 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    C5 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    N1 C5 C7 . . 116.2(2) ?
    N1 C5 C4 . . 122.4(2) ?
    C7 C5 C4 . . 121.34(19) ?
    O3 C6 C7 . . 122.7(2) ?
    O3 C6 C11 . . 116.03(19) ?
    C7 C6 C11 . . 121.28(19) ?
    C6 C7 C8 . . 117.5(2) ?
    C6 C7 C5 . . 122.24(19) ?
    C8 C7 C5 . . 120.3(2) ?
    C9 C8 C7 . . 122.2(2) ?
    C9 C8 H8 . . 118.9 ?
    C7 C8 H8 . . 118.9 ?
    C8 C9 C10 . . 120.9(2) ?
    C8 C9 H9 . . 119.5 ?
    C10 C9 H9 . . 119.5 ?
    C15 C10 C11 . . 118.6(2) ?
    C15 C10 C9 . . 123.0(2) ?
    C11 C10 C9 . . 118.4(2) ?
    C10 C11 C6 . . 119.6(2) ?
    C10 C11 C12 . . 118.8(2) ?
    C6 C11 C12 . . 121.6(2) ?
    C13 C12 C11 . . 120.2(2) ?
    C13 C12 H12 . . 119.9 ?
    C11 C12 H12 . . 119.9 ?
    C12 C13 C14 . . 121.1(3) ?
    C12 C13 H13 . . 119.4 ?
    C14 C13 H13 . . 119.4 ?
    C15 C14 C13 . . 120.1(3) ?
    C15 C14 H14 . . 119.9 ?
    C13 C14 H14 . . 119.9 ?
    C14 C15 C10 . . 121.1(2) ?
    C14 C15 H15 . . 119.4 ?
    C10 C15 H15 . . 119.4 ?
    C17 C16 H16A . . 109.5 ?
    C17 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C17 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    N2 C17 C19 . . 116.1(2) ?
    N2 C17 C16 . . 122.3(2) ?
    C19 C17 C16 . . 121.5(2) ?
    O4 C18 C19 . . 123.0(2) ?
    O4 C18 C23 . . 115.8(2) ?
    C19 C18 C23 . . 121.2(2) ?
    C18 C19 C20 . . 117.3(2) ?
    C18 C19 C17 . . 122.1(2) ?
    C20 C19 C17 . . 120.6(2) ?
    C21 C20 C19 . . 122.4(2) ?
    C21 C20 H20 . . 118.8 ?
    C19 C20 H20 . . 118.8 ?
    C20 C21 C22 . . 120.9(2) ?
    C20 C21 H21 . . 119.6 ?
    C22 C21 H21 . . 119.6 ?
    C23 C22 C21 . . 118.9(2) ?
    C23 C22 C27 . . 118.5(2) ?
    C21 C22 C27 . . 122.6(2) ?
    C22 C23 C24 . . 118.9(2) ?
    C22 C23 C18 . . 119.4(2) ?
    C24 C23 C18 . . 121.7(2) ?
    C25 C24 C23 . . 121.2(3) ?
    C25 C24 H24 . . 119.4 ?
    C23 C24 H24 . . 119.4 ?
    C24 C25 C26 . . 120.0(3) ?
    C24 C25 H25 . . 120.0 ?
    C26 C25 H25 . . 120.0 ?
    C27 C26 C25 . . 120.2(2) ?
    C27 C26 H26 . . 119.9 ?
    C25 C26 H26 . . 119.9 ?
    C26 C27 C22 . . 121.2(3) ?
    C26 C27 H27 . . 119.4 ?
    C22 C27 H27 . . 119.4 ?
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
    C5 N1 O1 C1 . . . . 168.65(19) ?
    C17 N2 O2 C3 . . . . -178.59(18) ?
    N1 O1 C1 C2 . . . . 178.37(17) ?
    O1 C1 C2 C3 . . . . 178.99(18) ?
    N2 O2 C3 C2 . . . . 72.6(2) ?
    C1 C2 C3 O2 . . . . 63.2(3) ?
    O1 N1 C5 C7 . . . . 179.14(16) ?
    O1 N1 C5 C4 . . . . -1.8(3) ?
    O3 C6 C7 C8 . . . . 178.1(2) ?
    C11 C6 C7 C8 . . . . -1.7(3) ?
    O3 C6 C7 C5 . . . . -0.5(3) ?
    C11 C6 C7 C5 . . . . 179.8(2) ?
    N1 C5 C7 C6 . . . . 7.2(3) ?
    C4 C5 C7 C6 . . . . -171.8(2) ?
    N1 C5 C7 C8 . . . . -171.3(2) ?
    C4 C5 C7 C8 . . . . 9.7(3) ?
    C6 C7 C8 C9 . . . . -0.1(3) ?
    C5 C7 C8 C9 . . . . 178.5(2) ?
    C7 C8 C9 C10 . . . . 0.8(4) ?
    C8 C9 C10 C15 . . . . 178.9(2) ?
    C8 C9 C10 C11 . . . . 0.2(3) ?
    C15 C10 C11 C6 . . . . 179.3(2) ?
    C9 C10 C11 C6 . . . . -1.9(3) ?
    C15 C10 C11 C12 . . . . -0.8(3) ?
    C9 C10 C11 C12 . . . . 178.0(2) ?
    O3 C6 C11 C10 . . . . -177.05(19) ?
    C7 C6 C11 C10 . . . . 2.7(3) ?
    O3 C6 C11 C12 . . . . 3.1(3) ?
    C7 C6 C11 C12 . . . . -177.2(2) ?
    C10 C11 C12 C13 . . . . 0.2(3) ?
    C6 C11 C12 C13 . . . . -179.9(2) ?
    C11 C12 C13 C14 . . . . 0.3(4) ?
    C12 C13 C14 C15 . . . . -0.2(4) ?
    C13 C14 C15 C10 . . . . -0.5(4) ?
    C11 C10 C15 C14 . . . . 1.0(4) ?
    C9 C10 C15 C14 . . . . -177.7(2) ?
    O2 N2 C17 C19 . . . . -179.28(16) ?
    O2 N2 C17 C16 . . . . -0.2(3) ?
    O4 C18 C19 C20 . . . . 178.18(19) ?
    C23 C18 C19 C20 . . . . -1.3(3) ?
    O4 C18 C19 C17 . . . . -1.4(3) ?
    C23 C18 C19 C17 . . . . 179.14(19) ?
    N2 C17 C19 C18 . . . . 4.1(3) ?
    C16 C17 C19 C18 . . . . -175.1(2) ?
    N2 C17 C19 C20 . . . . -175.5(2) ?
    C16 C17 C19 C20 . . . . 5.4(3) ?
    C18 C19 C20 C21 . . . . 0.3(3) ?
    C17 C19 C20 C21 . . . . 179.9(2) ?
    C19 C20 C21 C22 . . . . 0.8(4) ?
    C20 C21 C22 C23 . . . . -0.9(3) ?
    C20 C21 C22 C27 . . . . 178.8(2) ?
    C21 C22 C23 C24 . . . . 179.4(2) ?
    C27 C22 C23 C24 . . . . -0.3(3) ?
    C21 C22 C23 C18 . . . . -0.1(3) ?
    C27 C22 C23 C18 . . . . -179.8(2) ?
    O4 C18 C23 C22 . . . . -178.33(19) ?
    C19 C18 C23 C22 . . . . 1.2(3) ?
    O4 C18 C23 C24 . . . . 2.2(3) ?
    C19 C18 C23 C24 . . . . -178.3(2) ?
    C22 C23 C24 C25 . . . . 0.3(3) ?
    C18 C23 C24 C25 . . . . 179.8(2) ?
    C23 C24 C25 C26 . . . . -0.1(4) ?
    C24 C25 C26 C27 . . . . -0.1(4) ?
    C25 C26 C27 C22 . . . . 0.2(4) ?
    C23 C22 C27 C26 . . . . 0.1(3) ?
    C21 C22 C27 C26 . . . . -179.7(2) ?
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
    O3 H3 N1 . 0.82 1.83 2.543(2) 145.2 y
    O4 H4 N2 . 0.82 1.82 2.540(2) 145.6 y
    C12 H12 O3 2_766 0.93 2.68 3.588(3) 165.8 y
    C1 H1B Cg1 1_656 0.970 2.782 3.480(2) 129.41 y
