##############################################################################
#                                                                            #
# 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     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2012-03-06
_journal_date_accepted     2012-03-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      4
_journal_page_first     o1067
_journal_page_last     o1067
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812010549
_journal_coeditor_code     BQ2344
_publ_contact_author_name     'Prof. Tahir, Muhammad Nawaz'
_publ_contact_author_address
;
Department of Physics
University of Sargodha
Punjab
Pakistan
;
_publ_contact_author_email     'dmntahir_uos@yahoo.com, zsrkk@yahoo.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
(<i>E</i>)-3-[(2-Hydroxy-3-methoxybenzylidene)amino]benzoic acid
;
loop_
    _publ_author_name
    _publ_author_address
    'Kargar, Hadi'
;
Department of Chemistry,
Payame Noor University,
PO Box 19395-3697 Tehran,
I. R. of IRAN
;
    'Sharafi, Zahra'
;
Department of Chemistry,
Marvdasht Branch,
Islamic Azad University,
Marvdasht,
Iran
;
    'Kia, Reza'
;
      Department of Chemistry,
      Science and Research Branch,
      Islamic Azad University,
      Tehran,
      Iran
;
    'Ghelenji, Safoora'
;
Department of Chemistry,
North Tehran Branch,
Islamic Azad University,
Tehran,
Iran
;
    'Tahir, Muhammad Nawaz'
;
Department of Physics
University of Sargodha
Punjab
Pakistan
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(<i>E</i>)-3-[(2-Hydroxy-3-methoxybenzylidene)amino]benzoic acid
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C15 H13 N O4'
_chemical_formula_sum     'C15 H13 N O4'
_chemical_formula_iupac     'C15 H13 N O4'
_chemical_formula_weight     271.26
_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     5.2738(9)
_cell_length_b     10.978(2)
_cell_length_c     12.084(2)
_cell_angle_alpha     107.044(10)
_cell_angle_beta     100.776(11)
_cell_angle_gamma     97.539(10)
_cell_volume     644.1(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1456
_cell_measurement_theta_min     2.75
_cell_measurement_theta_max     28.76
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     'pale-yellow'
_exptl_crystal_size_max     0.19
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.399
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     284
_exptl_absorpt_coefficient_mu     0.103
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(<i>SADABS</i>; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.9808
_exptl_absorpt_correction_T_max     0.9908
_exptl_special_details     ?
_diffrn_ambient_temperature     296(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 APEXII CCD area-detector
;
_diffrn_measurement_method     '\f and \w scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8775
_diffrn_reflns_av_R_equivalents     0.0469
_diffrn_reflns_av_sigmaI/netI     0.0602
_diffrn_reflns_theta_min     2.21
_diffrn_reflns_theta_max     25.25
_diffrn_reflns_theta_full     25.25
_diffrn_measured_fraction_theta_max     0.986
_diffrn_measured_fraction_theta_full     0.986
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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     2308
_reflns_number_gt     1253
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1400
_refine_ls_R_factor_gt     0.0811
_refine_ls_wR_factor_gt     0.2038
_refine_ls_wR_factor_ref     0.2577
_refine_ls_goodness_of_fit_ref     1.049
_refine_ls_restrained_S_all     0.967
_refine_ls_number_reflns     2308
_refine_ls_number_parameters     279
_refine_ls_number_restraints     405
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.1461P)^2^+0.0613P] where P=(Fo^2^+2Fc^2^)/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     0.588
_refine_diff_density_min     -0.277
_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     'APEX2 (Bruker, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
                             'SHELXTL (Sheldrick, 2008) 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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.2047(6) -0.0156(3) 0.3825(3) 0.0503(9) Uani d . 1 1 . .
    C C2 0.3579(6) -0.0263(3) 0.2901(3) 0.0469(8) Uani d . 1 1 . .
    C C3 0.3065(7) -0.1382(3) 0.1929(3) 0.0605(10) Uani d . 1 1 . .
    H H3A 0.1755 -0.2078 0.1850 0.073 Uiso calc R 1 1 . .
    C C4 0.4508(7) -0.1461(3) 0.1075(3) 0.0659(11) Uani d . 1 1 . .
    H H4A 0.4174 -0.2212 0.0421 0.079 Uiso calc R 1 1 . .
    C C5 0.6418(7) -0.0437(3) 0.1192(3) 0.0537(9) Uani d . 1 1 A .
    H H5A 0.7389 -0.0505 0.0616 0.064 Uiso calc R 1 1 . .
    C C6 0.6948(6) 0.0696(3) 0.2142(3) 0.0461(8) Uani d . 1 1 . .
    C C7 0.5508(6) 0.0785(3) 0.3021(3) 0.0472(8) Uani d . 1 1 A .
    H H7A 0.5847 0.1537 0.3675 0.057 Uiso calc R 1 1 . .
    O O1 0.0350(5) -0.1160(2) 0.3720(2) 0.0663(8) Uani d . 1 1 . .
    O O2 0.2431(5) 0.0872(2) 0.4652(2) 0.0699(8) Uani d . 1 1 . .
    H H2 0.1331 0.0870 0.5202 0.105 Uiso d R 1 1 . .
    N N1 0.868(3) 0.1754(14) 0.215(2) 0.038(3) Uani d PDU 0.550(14) 1 A 1
    C C8 0.997(2) 0.2711(10) 0.3133(11) 0.051(3) Uani d PDU 0.550(14) 1 A 1
    H H8A 0.9624 0.2715 0.3861 0.061 Uiso calc PR 0.550(14) 1 A 1
    C C9 1.192(2) 0.3752(9) 0.3088(10) 0.054(4) Uani d PDU 0.550(14) 1 A 1
    C C10 1.307(8) 0.363(2) 0.213(3) 0.044(5) Uani d PDU 0.550(14) 1 A 1
    C C11 1.473(4) 0.4714(14) 0.2060(17) 0.058(5) Uani d PDU 0.550(14) 1 A 1
    C C12 1.552(7) 0.5805(19) 0.305(3) 0.062(6) Uani d PDU 0.550(14) 1 A 1
    H H12A 1.6724 0.6497 0.3034 0.075 Uiso calc PR 0.550(14) 1 A 1
    C C13 1.459(2) 0.5914(9) 0.4063(10) 0.075(3) Uani d PDU 0.550(14) 1 A 1
    H H13A 1.5152 0.6665 0.4722 0.090 Uiso calc PR 0.550(14) 1 A 1
    C C14 1.281(2) 0.4882(9) 0.4072(9) 0.073(3) Uani d PDU 0.550(14) 1 A 1
    H H14A 1.2184 0.4940 0.4752 0.088 Uiso calc PR 0.550(14) 1 A 1
    C C15 1.752(2) 0.5546(13) 0.0982(14) 0.080(4) Uani d PDU 0.550(14) 1 A 1
    H H15A 1.8146 0.5250 0.0272 0.121 Uiso calc PR 0.550(14) 1 A 1
    H H15B 1.8972 0.5807 0.1667 0.121 Uiso calc PR 0.550(14) 1 A 1
    H H15C 1.6696 0.6273 0.0964 0.121 Uiso calc PR 0.550(14) 1 A 1
    O O3 1.207(2) 0.2641(12) 0.1078(10) 0.065(3) Uani d PDU 0.550(14) 1 A 1
    H H3 1.0896 0.2127 0.1154 0.097 Uiso calc PR 0.550(14) 1 A 1
    O O4 1.565(2) 0.4519(10) 0.1044(8) 0.080(3) Uani d PDU 0.550(14) 1 A 1
    N N1A 0.929(4) 0.1671(17) 0.222(3) 0.038(3) Uani d PDU 0.450(14) 1 A 2
    C C8A 0.922(2) 0.2889(10) 0.2830(11) 0.038(3) Uani d PDU 0.450(14) 1 A 2
    H H8AA 0.7868 0.3062 0.3209 0.045 Uiso calc PR 0.450(14) 1 A 2
    C C9A 1.128(3) 0.3943(10) 0.2899(12) 0.044(3) Uani d PDU 0.450(14) 1 A 2
    C C10A 1.287(10) 0.374(2) 0.210(4) 0.041(4) Uani d PDU 0.450(14) 1 A 2
    C C11A 1.503(5) 0.4729(15) 0.2231(19) 0.044(3) Uani d PDU 0.450(14) 1 A 2
    C C12A 1.521(9) 0.595(2) 0.300(3) 0.062(5) Uani d PDU 0.450(14) 1 A 2
    H H12B 1.6540 0.6625 0.3042 0.074 Uiso calc PR 0.450(14) 1 A 2
    C C13A 1.344(3) 0.6185(9) 0.3695(10) 0.061(3) Uani d PDU 0.450(14) 1 A 2
    H H13B 1.3546 0.7023 0.4197 0.073 Uiso calc PR 0.450(14) 1 A 2
    C C14A 1.151(2) 0.5199(7) 0.3662(9) 0.057(3) Uani d PDU 0.450(14) 1 A 2
    H H14B 1.0346 0.5371 0.4153 0.068 Uiso calc PR 0.450(14) 1 A 2
    C C15A 1.854(3) 0.5432(16) 0.1425(16) 0.077(4) Uani d PDU 0.450(14) 1 A 2
    H H15D 1.9220 0.5133 0.0732 0.115 Uiso calc PR 0.450(14) 1 A 2
    H H15E 1.9947 0.5697 0.2127 0.115 Uiso calc PR 0.450(14) 1 A 2
    H H15F 1.7723 0.6156 0.1387 0.115 Uiso calc PR 0.450(14) 1 A 2
    O O3A 1.295(3) 0.2529(14) 0.1380(15) 0.062(4) Uani d PDU 0.450(14) 1 A 2
    H H3B 1.1719 0.1997 0.1393 0.093 Uiso calc PR 0.450(14) 1 A 2
    O O4A 1.661(2) 0.4394(11) 0.1466(11) 0.062(3) Uani d PDU 0.450(14) 1 A 2
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.049(2) 0.0358(17) 0.064(2) -0.0037(15) 0.0263(17) 0.0113(16)
    C2 0.0416(18) 0.0415(17) 0.061(2) 0.0011(15) 0.0226(16) 0.0186(16)
    C3 0.058(2) 0.0408(18) 0.076(2) -0.0084(16) 0.029(2) 0.0086(17)
    C4 0.074(3) 0.0459(19) 0.069(2) -0.0080(18) 0.035(2) 0.0019(17)
    C5 0.054(2) 0.0481(19) 0.054(2) -0.0007(16) 0.0273(17) 0.0053(16)
    C6 0.0400(18) 0.0430(17) 0.057(2) 0.0004(14) 0.0226(16) 0.0162(15)
    C7 0.0413(18) 0.0389(17) 0.059(2) -0.0023(14) 0.0248(16) 0.0097(15)
    O1 0.0638(16) 0.0449(13) 0.0852(18) -0.0150(11) 0.0389(14) 0.0117(12)
    O2 0.0772(18) 0.0519(15) 0.0748(18) -0.0139(13) 0.0489(14) 0.0046(13)
    N1 0.017(7) 0.044(2) 0.053(3) 0.003(3) 0.015(5) 0.013(2)
    C8 0.045(6) 0.055(5) 0.046(5) -0.002(4) 0.012(4) 0.010(4)
    C9 0.048(6) 0.050(4) 0.057(5) 0.001(4) 0.025(5) 0.003(4)
    C10 0.038(8) 0.038(6) 0.047(5) -0.002(6) 0.014(5) 0.002(5)
    C11 0.038(6) 0.054(5) 0.065(7) -0.007(5) 0.025(6) -0.004(5)
    C12 0.045(8) 0.051(7) 0.080(7) -0.014(7) 0.027(6) 0.007(6)
    C13 0.058(6) 0.057(5) 0.082(6) -0.015(4) 0.037(5) -0.018(4)
    C14 0.063(6) 0.068(5) 0.070(5) -0.015(4) 0.038(5) -0.005(4)
    C15 0.057(7) 0.079(6) 0.105(10) -0.012(5) 0.043(7) 0.027(6)
    O3 0.057(7) 0.052(5) 0.067(5) -0.018(4) 0.037(5) -0.009(4)
    O4 0.073(6) 0.073(4) 0.075(5) -0.030(4) 0.040(4) 0.004(4)
    N1A 0.017(7) 0.044(2) 0.053(3) 0.003(3) 0.015(5) 0.013(2)
    C8A 0.027(5) 0.042(4) 0.047(7) 0.008(3) 0.021(4) 0.010(4)
    C9A 0.040(6) 0.034(4) 0.057(6) 0.000(4) 0.020(5) 0.013(4)
    C10A 0.030(7) 0.033(5) 0.062(8) 0.004(5) 0.021(6) 0.013(5)
    C11A 0.042(7) 0.042(5) 0.054(7) 0.001(4) 0.017(5) 0.023(5)
    C12A 0.055(10) 0.044(6) 0.077(8) -0.006(6) 0.020(7) 0.009(6)
    C13A 0.071(7) 0.036(4) 0.066(6) -0.004(4) 0.022(5) 0.005(4)
    C14A 0.060(6) 0.039(4) 0.070(6) 0.006(4) 0.028(5) 0.010(4)
    C15A 0.067(9) 0.069(7) 0.099(11) -0.017(7) 0.035(7) 0.039(7)
    O3A 0.059(8) 0.038(4) 0.084(8) -0.002(5) 0.041(6) 0.002(5)
    O4A 0.050(5) 0.064(4) 0.076(7) -0.009(4) 0.039(5) 0.024(4)
_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
    C1 O2 . 1.232(4) ?
    C1 O1 . 1.284(4) ?
    C1 C2 . 1.482(5) ?
    C2 C3 . 1.382(4) ?
    C2 C7 . 1.385(4) ?
    C3 C4 . 1.382(5) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.361(4) ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.376(4) ?
    C5 H5A . 0.9300 ?
    C6 N1 . 1.38(2) ?
    C6 C7 . 1.405(4) ?
    C6 N1A . 1.49(3) ?
    C7 H7A . 0.9300 ?
    O2 H2 . 0.9612 ?
    N1 C8 . 1.329(13) ?
    C8 C9 . 1.454(9) ?
    C8 H8A . 0.9300 ?
    C9 C10 . 1.383(11) ?
    C9 C14 . 1.395(9) ?
    C10 O3 . 1.365(18) ?
    C10 C11 . 1.418(13) ?
    C11 C12 . 1.370(15) ?
    C11 O4 . 1.373(11) ?
    C12 C13 . 1.384(16) ?
    C12 H12A . 0.9300 ?
    C13 C14 . 1.378(9) ?
    C13 H13A . 0.9300 ?
    C14 H14A . 0.9300 ?
    C15 O4 . 1.426(9) ?
    C15 H15A . 0.9600 ?
    C15 H15B . 0.9600 ?
    C15 H15C . 0.9600 ?
    O3 H3 . 0.8200 ?
    N1A C8A . 1.333(13) ?
    C8A C9A . 1.450(10) ?
    C8A H8AA . 0.9300 ?
    C9A C10A . 1.382(12) ?
    C9A C14A . 1.391(10) ?
    C10A O3A . 1.368(19) ?
    C10A C11A . 1.419(14) ?
    C11A O4A . 1.362(12) ?
    C11A C12A . 1.367(16) ?
    C12A C13A . 1.374(17) ?
    C12A H12B . 0.9300 ?
    C13A C14A . 1.370(10) ?
    C13A H13B . 0.9300 ?
    C14A H14B . 0.9300 ?
    C15A O4A . 1.443(10) ?
    C15A H15D . 0.9600 ?
    C15A H15E . 0.9600 ?
    C15A H15F . 0.9600 ?
    O3A H3B . 0.8200 ?
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
    O2 C1 O1 . . 122.7(3) ?
    O2 C1 C2 . . 119.7(3) ?
    O1 C1 C2 . . 117.6(3) ?
    C3 C2 C7 . . 120.6(3) ?
    C3 C2 C1 . . 120.5(3) ?
    C7 C2 C1 . . 118.9(3) ?
    C2 C3 C4 . . 119.7(3) ?
    C2 C3 H3A . . 120.2 ?
    C4 C3 H3A . . 120.2 ?
    C5 C4 C3 . . 120.0(3) ?
    C5 C4 H4A . . 120.0 ?
    C3 C4 H4A . . 120.0 ?
    C4 C5 C6 . . 121.7(3) ?
    C4 C5 H5A . . 119.2 ?
    C6 C5 H5A . . 119.2 ?
    C5 C6 N1 . . 119.2(10) ?
    C5 C6 C7 . . 118.9(3) ?
    N1 C6 C7 . . 121.5(9) ?
    C5 C6 N1A . . 115.4(10) ?
    N1 C6 N1A . . 13.2(17) ?
    C7 C6 N1A . . 125.2(11) ?
    C2 C7 C6 . . 119.2(3) ?
    C2 C7 H7A . . 120.4 ?
    C6 C7 H7A . . 120.4 ?
    C1 O2 H2 . . 114.7 ?
    C8 N1 C6 . . 123(2) ?
    N1 C8 C9 . . 120.7(14) ?
    N1 C8 H8A . . 119.6 ?
    C9 C8 H8A . . 119.6 ?
    C10 C9 C14 . . 118.3(8) ?
    C10 C9 C8 . . 122.2(8) ?
    C14 C9 C8 . . 119.4(8) ?
    O3 C10 C9 . . 121.7(12) ?
    O3 C10 C11 . . 115.0(19) ?
    C9 C10 C11 . . 120.3(8) ?
    C12 C11 O4 . . 125.4(9) ?
    C12 C11 C10 . . 118.0(14) ?
    O4 C11 C10 . . 116.1(9) ?
    C11 C12 C13 . . 122.4(10) ?
    C11 C12 H12A . . 118.8 ?
    C13 C12 H12A . . 118.8 ?
    C14 C13 C12 . . 118.3(8) ?
    C14 C13 H13A . . 120.9 ?
    C12 C13 H13A . . 120.9 ?
    C13 C14 C9 . . 121.8(7) ?
    C13 C14 H14A . . 119.1 ?
    C9 C14 H14A . . 119.1 ?
    C11 O4 C15 . . 118.0(9) ?
    C8A N1A C6 . . 113.9(18) ?
    N1A C8A C9A . . 119.6(14) ?
    N1A C8A H8AA . . 120.2 ?
    C9A C8A H8AA . . 120.2 ?
    C10A C9A C14A . . 118.6(10) ?
    C10A C9A C8A . . 119.5(9) ?
    C14A C9A C8A . . 121.5(10) ?
    O3A C10A C9A . . 123.2(14) ?
    O3A C10A C11A . . 115(2) ?
    C9A C10A C11A . . 119.5(10) ?
    O4A C11A C12A . . 125.1(11) ?
    O4A C11A C10A . . 115.2(10) ?
    C12A C11A C10A . . 119.3(16) ?
    C11A C12A C13A . . 120.0(13) ?
    C11A C12A H12B . . 120.0 ?
    C13A C12A H12B . . 120.0 ?
    C14A C13A C12A . . 120.9(10) ?
    C14A C13A H13B . . 119.5 ?
    C12A C13A H13B . . 119.5 ?
    C13A C14A C9A . . 120.4(9) ?
    C13A C14A H14B . . 119.8 ?
    C9A C14A H14B . . 119.8 ?
    O4A C15A H15D . . 109.5 ?
    O4A C15A H15E . . 109.5 ?
    H15D C15A H15E . . 109.5 ?
    O4A C15A H15F . . 109.5 ?
    H15D C15A H15F . . 109.5 ?
    H15E C15A H15F . . 109.5 ?
    C10A O3A H3B . . 109.5 ?
    C11A O4A C15A . . 116.8(11) ?
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
    O2 C1 C2 C3 . . . . -176.1(3) ?
    O1 C1 C2 C3 . . . . 3.8(5) ?
    O2 C1 C2 C7 . . . . 3.1(5) ?
    O1 C1 C2 C7 . . . . -177.1(3) ?
    C7 C2 C3 C4 . . . . 0.6(5) ?
    C1 C2 C3 C4 . . . . 179.8(3) ?
    C2 C3 C4 C5 . . . . -0.2(6) ?
    C3 C4 C5 C6 . . . . -0.7(6) ?
    C4 C5 C6 N1 . . . . -172.3(11) ?
    C4 C5 C6 C7 . . . . 1.2(5) ?
    C4 C5 C6 N1A . . . . 173.4(14) ?
    C3 C2 C7 C6 . . . . -0.1(5) ?
    C1 C2 C7 C6 . . . . -179.3(3) ?
    C5 C6 C7 C2 . . . . -0.7(5) ?
    N1 C6 C7 C2 . . . . 172.6(11) ?
    N1A C6 C7 C2 . . . . -172.2(14) ?
    C5 C6 N1 C8 . . . . -157.2(13) ?
    C7 C6 N1 C8 . . . . 29(2) ?
    N1A C6 N1 C8 . . . . -81(10) ?
    C6 N1 C8 C9 . . . . 175.3(12) ?
    N1 C8 C9 C10 . . . . -19(3) ?
    N1 C8 C9 C14 . . . . 165.7(13) ?
    C14 C9 C10 O3 . . . . -171(3) ?
    C8 C9 C10 O3 . . . . 14(5) ?
    C14 C9 C10 C11 . . . . -12(5) ?
    C8 C9 C10 C11 . . . . 173(3) ?
    O3 C10 C11 C12 . . . . 172(4) ?
    C9 C10 C11 C12 . . . . 11(7) ?
    O3 C10 C11 O4 . . . . -16(5) ?
    C9 C10 C11 O4 . . . . -176(3) ?
    O4 C11 C12 C13 . . . . -177(3) ?
    C10 C11 C12 C13 . . . . -5(7) ?
    C11 C12 C13 C14 . . . . 0(5) ?
    C12 C13 C14 C9 . . . . -1(3) ?
    C10 C9 C14 C13 . . . . 7(3) ?
    C8 C9 C14 C13 . . . . -177.9(9) ?
    C12 C11 O4 C15 . . . . -2(4) ?
    C10 C11 O4 C15 . . . . -174(3) ?
    C5 C6 N1A C8A . . . . 156.3(18) ?
    N1 C6 N1A C8A . . . . 46(7) ?
    C7 C6 N1A C8A . . . . -32(3) ?
    C6 N1A C8A C9A . . . . -175.4(16) ?
    N1A C8A C9A C10A . . . . 17(4) ?
    N1A C8A C9A C14A . . . . -170.5(19) ?
    C14A C9A C10A O3A . . . . 175(4) ?
    C8A C9A C10A O3A . . . . -13(7) ?
    C14A C9A C10A C11A . . . . 13(7) ?
    C8A C9A C10A C11A . . . . -174(4) ?
    O3A C10A C11A O4A . . . . 11(6) ?
    C9A C10A C11A O4A . . . . 174(4) ?
    O3A C10A C11A C12A . . . . -176(4) ?
    C9A C10A C11A C12A . . . . -13(8) ?
    O4A C11A C12A C13A . . . . 177(3) ?
    C10A C11A C12A C13A . . . . 5(8) ?
    C11A C12A C13A C14A . . . . 2(7) ?
    C12A C13A C14A C9A . . . . -1(3) ?
    C10A C9A C14A C13A . . . . -6(4) ?
    C8A C9A C14A C13A . . . . -178.7(11) ?
    C12A C11A O4A C15A . . . . -3(5) ?
    C10A C11A O4A C15A . . . . 169(4) ?
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
    O2 H2 O1 2_556 0.96 1.69 2.638(4) 169 y
    O3 H3 N1 . 0.82 1.92 2.64(2) 147 y
    C15A H15E Cg1 1_655 0.96 2.90 3.757(11) 139 y
    C15A H15E Cg2 1_655 0.96 2.83 3.680(12) 139 y