##############################################################################
###                                                                        ###
###        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                                                              #
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# 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.                                        #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2009-09-04
_journal_date_accepted     2009-09-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     10
_journal_page_first     o2573
_journal_page_last     o2573
_journal_paper_category     QO
_journal_coeditor_code     DN2481
_publ_contact_author_name     'Assoc Prof Dr Hadariah Bahron'
_publ_contact_author_address
;
     Faculty of Applied Sciences
     Universiti Teknologi MARA
     40450 Shah Alam, Selangor, Malaysia
;
_publ_contact_author_email     'hadariah@salam.uitm.edu.my'
_publ_contact_author_fax     '6 03 55443210'
_publ_contact_author_phone     '6 03 55443504'
_publ_section_title
;\
6,6'-Dimethoxy-2,2'-[(E,E')-(4-chloro-m-phenylene)\
bis(nitrilomethylidyne)]diphenol
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Yamin, Bohari M.' ?
;     School of Chemical Sciences and Food Technology
      Univeriti  Kebangsaan Malaysia
      UKM 43500 Bangi Selangor. Malaysia
;
    'Bakar, Siti Najihah A.' ?
;    Department of Chemistry
     Faculty of Applied Sciences
     Universiti Teknologi MARA
     40450 Shah Alam, Selangor, Malaysia
;
    'Kassim, Karimah' ?
;    Department of Chemistry
     Faculty of Applied Sciences
     Universiti Teknologi MARA
     40450 Shah Alam, Selangor, Malaysia
;
    'Bahron, Hadariah' ?
;    Department of Chemistry
     Faculty of Applied Sciences
     Universiti Teknologi MARA
     40450 Shah Alam, Selangor, Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
6,6'-Dimethoxy-2,2'-[(E,E')-(4-chloro-m-
phenylene)bis(nitrilomethylidyne)]diphenol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H19 Cl N2 O4'
_chemical_formula_sum     'C22 H19 Cl N2 O4'
_chemical_formula_iupac     'C22 H19 Cl N2 O4'
_chemical_formula_weight     410.84
_chemical_melting_point     ?
_chemical_melting_point_gt     468.0
_chemical_melting_point_lt     470.0
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     9.900(2)
_cell_length_b     6.8589(12)
_cell_length_c     28.830(6)
_cell_angle_alpha     90.00
_cell_angle_beta     94.659(4)
_cell_angle_gamma     90.00
_cell_volume     1951.2(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2429
_cell_measurement_theta_min     1.4
_cell_measurement_theta_max     26.5
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.41
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.399
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     856
_exptl_absorpt_coefficient_mu     0.228
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.912
_exptl_absorpt_correction_T_max     0.975
_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
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     83.66
_diffrn_reflns_number     12204
_diffrn_reflns_av_R_equivalents     0.0303
_diffrn_reflns_av_sigmaI/netI     0.0341
_diffrn_reflns_theta_min     1.4
_diffrn_reflns_theta_max     26.5
_diffrn_reflns_theta_full     26.5
_diffrn_measured_fraction_theta_max     1.00
_diffrn_measured_fraction_theta_full     1.00
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -29
_diffrn_reflns_limit_l_max     36
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_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     4049
_reflns_number_gt     2758
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.087
_refine_ls_R_factor_gt     0.055
_refine_ls_wR_factor_gt     0.1173
_refine_ls_wR_factor_ref     0.1306
_refine_ls_goodness_of_fit_ref     1.06
_refine_ls_restrained_S_all     1.06
_refine_ls_number_reflns     4049
_refine_ls_number_parameters     272
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0536P)²+0.4146P] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.21
_refine_diff_density_min     -0.17
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT (Bruker, 2000)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON
(Spek, 2009)
;
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
    O O1 0.4334(2) 0.6076(3) 1.14002(7) 0.0751(5) Uani d . 1 . .
    O O2 0.5923(2) 0.6402(2) 1.07204(7) 0.0671(5) Uani d D 1 . .
    O O3 0.90619(18) -0.3720(3) 0.77614(6) 0.0682(5) Uani d . 1 . .
    O O4 0.86271(17) -0.0603(3) 0.82460(7) 0.0655(5) Uani d D 1 . .
    Cl Cl1 0.83872(7) 0.86091(8) 1.00563(2) 0.0658(2) Uani d . 1 . .
    N N2 0.9571(2) 0.2143(3) 0.87964(6) 0.0560(5) Uani d . 1 . .
    N N1 0.71450(19) 0.4773(2) 1.00623(7) 0.0496(5) Uani d . 1 . .
    C C5 0.8366(2) 0.3491(3) 0.94045(8) 0.0523(6) Uani d . 1 . .
    H H5 0.7886 0.2325 0.9402 0.063 Uiso calc R 1 . .
    C C6 0.8069(2) 0.4937(3) 0.97170(8) 0.0470(5) Uani d . 1 . .
    C C1 0.8754(2) 0.6715(3) 0.96890(8) 0.0497(6) Uani d . 1 . .
    C C2 0.9714(3) 0.6982(3) 0.93761(8) 0.0594(7) Uani d . 1 . .
    H H2A 1.0153 0.8177 0.9363 0.071 Uiso calc R 1 . .
    C C3 1.0032(3) 0.5503(4) 0.90814(8) 0.0602(7) Uani d . 1 . .
    H H3 1.0695 0.5683 0.8874 0.072 Uiso calc R 1 . .
    C C4 0.9347(2) 0.3727(3) 0.90976(8) 0.0519(6) Uani d . 1 . .
    C C7 0.6600(2) 0.3163(3) 1.01624(8) 0.0509(6) Uani d . 1 . .
    H H7 0.6779 0.2059 0.9990 0.061 Uiso calc R 1 . .
    C C8 0.5717(2) 0.2992(3) 1.05322(8) 0.0474(5) Uani d . 1 . .
    C C9 0.5173(3) 0.1175(3) 1.06386(9) 0.0572(6) Uani d . 1 . .
    H H9 0.5382 0.0082 1.0468 0.069 Uiso calc R 1 . .
    C C10 0.4341(3) 0.0992(3) 1.09897(10) 0.0633(7) Uani d . 1 . .
    H H10 0.3987 -0.0222 1.1057 0.076 Uiso calc R 1 . .
    C C11 0.4019(2) 0.2612(4) 1.12488(9) 0.0590(6) Uani d . 1 . .
    H H11 0.3432 0.2482 1.1483 0.071 Uiso calc R 1 . .
    C C12 0.4565(2) 0.4408(3) 1.11604(8) 0.0542(6) Uani d . 1 . .
    C C13 0.5416(2) 0.4621(3) 1.08000(8) 0.0491(6) Uani d . 1 . .
    C C15 1.0764(3) 0.1673(4) 0.86971(8) 0.0591(6) Uani d . 1 . .
    H H15 1.1497 0.2411 0.8819 0.071 Uiso calc R 1 . .
    C C16 1.1010(2) 0.0026(4) 0.84010(8) 0.0549(6) Uani d . 1 . .
    C C17 1.2336(3) -0.0564(5) 0.83404(10) 0.0728(8) Uani d . 1 . .
    H H17 1.3061 0.0163 0.8473 0.087 Uiso calc R 1 . .
    C C18 1.2577(3) -0.2191(5) 0.80892(10) 0.0788(8) Uani d . 1 . .
    H H18 1.3463 -0.2582 0.8056 0.095 Uiso calc R 1 . .
    C C19 1.1499(3) -0.3269(4) 0.78828(9) 0.0687(7) Uani d . 1 . .
    H H19 1.1673 -0.4366 0.7708 0.082 Uiso calc R 1 . .
    C C20 1.0186(2) -0.2735(4) 0.79340(8) 0.0549(6) Uani d . 1 . .
    C C21 0.9926(2) -0.1070(4) 0.81969(8) 0.0521(6) Uani d . 1 . .
    C C14 0.3549(3) 0.5911(5) 1.17851(11) 0.0893(9) Uani d . 1 . .
    H H14A 0.2687 0.5341 1.1687 0.134 Uiso calc R 1 . .
    H H14B 0.3412 0.7181 1.1913 0.134 Uiso calc R 1 . .
    H H14C 0.4013 0.5098 1.2018 0.134 Uiso calc R 1 . .
    C C22 0.9258(3) -0.5492(4) 0.75161(11) 0.0839(9) Uani d . 1 . .
    H H22A 0.9725 -0.5221 0.7244 0.126 Uiso calc R 1 . .
    H H22B 0.8394 -0.6070 0.7425 0.126 Uiso calc R 1 . .
    H H22C 0.9787 -0.6377 0.7714 0.126 Uiso calc R 1 . .
    H H4 0.861(3) 0.027(4) 0.8438(9) 0.102(12) Uiso d D 1 . .
    H H2 0.643(3) 0.620(5) 1.0511(9) 0.110(13) Uiso d D 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
    O1 C12 . 1.366(3) ?
    O1 C14 . 1.410(3) ?
    O2 C13 . 1.348(3) ?
    O2 H2 . 0.83(3) ?
    O3 C20 . 1.361(3) ?
    O3 C22 . 1.427(3) ?
    O4 C21 . 1.343(3) ?
    O4 H4 . 0.82(2) ?
    Cl1 C1 . 1.733(2) ?
    N2 C15 . 1.279(3) ?
    N2 C4 . 1.419(3) ?
    N1 C7 . 1.273(3) ?
    N1 C6 . 1.410(3) ?
    C5 C4 . 1.376(3) ?
    C5 C6 . 1.388(3) ?
    C5 H5 . 0.9300 ?
    C6 C1 . 1.401(3) ?
    C1 C2 . 1.375(3) ?
    C2 C3 . 1.377(3) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.397(3) ?
    C3 H3 . 0.9300 ?
    C7 C8 . 1.438(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.402(3) ?
    C8 C13 . 1.403(3) ?
    C9 C10 . 1.361(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.390(4) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.378(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.397(3) ?
    C15 C16 . 1.448(3) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.398(4) ?
    C16 C21 . 1.401(3) ?
    C17 C18 . 1.362(4) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.391(4) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.370(4) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.406(3) ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    C22 H22A . 0.9600 ?
    C22 H22B . 0.9600 ?
    C22 H22C . 0.9600 ?
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
    C12 O1 C14 . . 117.2(2) ?
    C13 O2 H2 . . 103(2) ?
    C20 O3 C22 . . 117.6(2) ?
    C21 O4 H4 . . 109(2) ?
    C15 N2 C4 . . 121.5(2) ?
    C7 N1 C6 . . 122.7(2) ?
    C4 C5 C6 . . 122.1(2) ?
    C4 C5 H5 . . 119.0 ?
    C6 C5 H5 . . 119.0 ?
    C5 C6 C1 . . 117.1(2) ?
    C5 C6 N1 . . 125.8(2) ?
    C1 C6 N1 . . 117.1(2) ?
    C2 C1 C6 . . 121.2(2) ?
    C2 C1 Cl1 . . 119.44(17) ?
    C6 C1 Cl1 . . 119.39(19) ?
    C1 C2 C3 . . 120.8(2) ?
    C1 C2 H2A . . 119.6 ?
    C3 C2 H2A . . 119.6 ?
    C2 C3 C4 . . 119.1(2) ?
    C2 C3 H3 . . 120.5 ?
    C4 C3 H3 . . 120.5 ?
    C5 C4 C3 . . 119.6(2) ?
    C5 C4 N2 . . 117.2(2) ?
    C3 C4 N2 . . 123.2(2) ?
    N1 C7 C8 . . 122.2(2) ?
    N1 C7 H7 . . 118.9 ?
    C8 C7 H7 . . 118.9 ?
    C9 C8 C13 . . 119.0(2) ?
    C9 C8 C7 . . 120.2(2) ?
    C13 C8 C7 . . 120.8(2) ?
    C10 C9 C8 . . 120.7(2) ?
    C10 C9 H9 . . 119.6 ?
    C8 C9 H9 . . 119.6 ?
    C9 C10 C11 . . 120.3(2) ?
    C9 C10 H10 . . 119.8 ?
    C11 C10 H10 . . 119.8 ?
    C12 C11 C10 . . 120.3(2) ?
    C12 C11 H11 . . 119.8 ?
    C10 C11 H11 . . 119.8 ?
    O1 C12 C11 . . 124.8(2) ?
    O1 C12 C13 . . 115.1(2) ?
    C11 C12 C13 . . 120.0(2) ?
    O2 C13 C12 . . 118.4(2) ?
    O2 C13 C8 . . 122.0(2) ?
    C12 C13 C8 . . 119.6(2) ?
    N2 C15 C16 . . 122.1(2) ?
    N2 C15 H15 . . 119.0 ?
    C16 C15 H15 . . 119.0 ?
    C17 C16 C21 . . 119.2(2) ?
    C17 C16 C15 . . 120.3(2) ?
    C21 C16 C15 . . 120.4(2) ?
    C18 C17 C16 . . 120.7(3) ?
    C18 C17 H17 . . 119.7 ?
    C16 C17 H17 . . 119.7 ?
    C17 C18 C19 . . 120.1(3) ?
    C17 C18 H18 . . 120.0 ?
    C19 C18 H18 . . 120.0 ?
    C20 C19 C18 . . 120.9(3) ?
    C20 C19 H19 . . 119.6 ?
    C18 C19 H19 . . 119.6 ?
    O3 C20 C19 . . 125.7(2) ?
    O3 C20 C21 . . 114.8(2) ?
    C19 C20 C21 . . 119.5(2) ?
    O4 C21 C16 . . 122.3(2) ?
    O4 C21 C20 . . 118.0(2) ?
    C16 C21 C20 . . 119.7(2) ?
    O1 C14 H14A . . 109.5 ?
    O1 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    O1 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    O3 C22 H22A . . 109.5 ?
    O3 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    O3 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 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
    C4 C5 C6 C1 . . . . 3.9(3) ?
    C4 C5 C6 N1 . . . . -175.7(2) ?
    C7 N1 C6 C5 . . . . 9.1(3) ?
    C7 N1 C6 C1 . . . . -170.4(2) ?
    C5 C6 C1 C2 . . . . -2.3(3) ?
    N1 C6 C1 C2 . . . . 177.3(2) ?
    C5 C6 C1 Cl1 . . . . 177.84(16) ?
    N1 C6 C1 Cl1 . . . . -2.5(3) ?
    C6 C1 C2 C3 . . . . -0.2(4) ?
    Cl1 C1 C2 C3 . . . . 179.66(18) ?
    C1 C2 C3 C4 . . . . 1.2(4) ?
    C6 C5 C4 C3 . . . . -3.0(3) ?
    C6 C5 C4 N2 . . . . 179.5(2) ?
    C2 C3 C4 C5 . . . . 0.3(4) ?
    C2 C3 C4 N2 . . . . 177.6(2) ?
    C15 N2 C4 C5 . . . . -140.9(2) ?
    C15 N2 C4 C3 . . . . 41.7(3) ?
    C6 N1 C7 C8 . . . . 176.54(19) ?
    N1 C7 C8 C9 . . . . -178.1(2) ?
    N1 C7 C8 C13 . . . . 0.1(3) ?
    C13 C8 C9 C10 . . . . 1.4(3) ?
    C7 C8 C9 C10 . . . . 179.6(2) ?
    C8 C9 C10 C11 . . . . 0.0(4) ?
    C9 C10 C11 C12 . . . . -1.6(4) ?
    C14 O1 C12 C11 . . . . 4.3(4) ?
    C14 O1 C12 C13 . . . . -176.2(2) ?
    C10 C11 C12 O1 . . . . -178.7(2) ?
    C10 C11 C12 C13 . . . . 1.9(4) ?
    O1 C12 C13 O2 . . . . -0.1(3) ?
    C11 C12 C13 O2 . . . . 179.4(2) ?
    O1 C12 C13 C8 . . . . -179.99(19) ?
    C11 C12 C13 C8 . . . . -0.5(3) ?
    C9 C8 C13 O2 . . . . 179.0(2) ?
    C7 C8 C13 O2 . . . . 0.8(3) ?
    C9 C8 C13 C12 . . . . -1.1(3) ?
    C7 C8 C13 C12 . . . . -179.4(2) ?
    C4 N2 C15 C16 . . . . 178.2(2) ?
    N2 C15 C16 C17 . . . . -173.3(2) ?
    N2 C15 C16 C21 . . . . 2.5(4) ?
    C21 C16 C17 C18 . . . . -0.5(4) ?
    C15 C16 C17 C18 . . . . 175.4(3) ?
    C16 C17 C18 C19 . . . . 1.1(4) ?
    C17 C18 C19 C20 . . . . -1.0(4) ?
    C22 O3 C20 C19 . . . . 1.8(4) ?
    C22 O3 C20 C21 . . . . -176.1(2) ?
    C18 C19 C20 O3 . . . . -177.6(2) ?
    C18 C19 C20 C21 . . . . 0.3(4) ?
    C17 C16 C21 O4 . . . . 179.1(2) ?
    C15 C16 C21 O4 . . . . 3.3(3) ?
    C17 C16 C21 C20 . . . . -0.2(3) ?
    C15 C16 C21 C20 . . . . -176.1(2) ?
    O3 C20 C21 O4 . . . . -0.9(3) ?
    C19 C20 C21 O4 . . . . -179.0(2) ?
    O3 C20 C21 C16 . . . . 178.4(2) ?
    C19 C20 C21 C16 . . . . 0.3(3) ?
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
    O2 H2 N1 . . 1_555 0.83(3) 1.81(3) 2.586(3) 155(3) yes
    O4 H4 N2 . . 1_555 0.82(3) 1.86(3) 2.588(3) 148(3) yes
    C11 H11 O4 . . 3_657 0.93 2.59 3.392(3) 145 yes
    C3 H3 Cg3 . . 1_565 0.93 2.89 3.635(3) 138 yes
