##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section B. It 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 may be obtained from        #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# 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                                                              #
#                                                                            #
#           Copyright International Union of Crystallography                 #
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##############################################################################

data_global
_audit_creation_method     'from SHELXL-97 with Word-Perfect Macro PRPKAPPA'
_journal_date_recd_electronic     2004-10-25
_journal_date_accepted     2005-02-23
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2005
_journal_volume     61
_journal_issue      3
_journal_page_first     321
_journal_page_last     328
_publ_contact_author_name
;
Dr Christopher Glidewell
;
_publ_contact_author_address
;
University of St Andrews,
Fife KY16 9ST, UK
;
_publ_contact_author_email     'cg@st-andrews.ac.uk'
_publ_contact_author_fax     '+1334-463808'
_publ_contact_author_phone     '+1334-463839'
_publ_section_title
;
Concomitant polymorphism and a temperature-dependent phase change in
(E)-[1-(4-methoxyphenyl)-3-phenyl-2-propenylideneamino)oxyacetic acid
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Skakle, Janet M. S.' .
;    Department of Chemistry, University of Aberdeen,
     Meston Walk, Old Aberdeen, AB24 3UE, UK
;
    'Low, John N.' .
;     Department of Chemistry, University of Aberdeen, Meston Walk,
      Old Aberdeen, AB24 3UE, UK
;
    'Wardell, James L.' .
;    Instituto de Química, Departamento de Química Inorgânica,
     Universidade Federal do Rio de Janeiro,
     21945-970 Rio de Janeiro-RJ, Brazil
;
    'Glidewell, Christopher' .
;    School of Chemistry, University of St Andrews,
     St Andrews, Fife, KY16 9ST, UK
;
data_I
_chemical_name_systematic
;
(E)-[1-(4-methoxyphenyl)-3-phenyl-2-propenylideneamino)oxyacetic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H17 N O4'
_chemical_formula_sum     'C18 H17 N O4'
_chemical_formula_weight     311.33
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x, -y+1/2, z+1/2'
    '-x, -y, -z'
    '-x, y-1/2, -z-1/2'
_cell_length_a     8.5153(7)
_cell_length_b     16.0591(13)
_cell_length_c     12.1476(10)
_cell_angle_alpha     90.00
_cell_angle_beta     96.801(2)
_cell_angle_gamma     90.00
_cell_volume     1649.5(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5963
_cell_measurement_theta_min     2.11
_cell_measurement_theta_max     32.58
_cell_measurement_temperature     291(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.254
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     656
_exptl_absorpt_coefficient_mu     0.089
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS, Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.952
_exptl_absorpt_correction_T_max     0.996
_exptl_special_details
;
?
;
_diffrn_ambient_temperature     291(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method     φ-ω
_diffrn_reflns_number     16995
_diffrn_reflns_av_R_equivalents     0.0581
_diffrn_reflns_av_sigmaI/netI     0.0936
_diffrn_reflns_theta_min     2.11
_diffrn_reflns_theta_max     32.58
_diffrn_reflns_theta_full     32.58
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     24
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     18
_diffrn_standards_decay_%     negligible
_reflns_number_total     5963
_reflns_number_gt     1586
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.2369
_refine_ls_R_factor_gt     0.0561
_refine_ls_wR_factor_gt     0.1166
_refine_ls_wR_factor_ref     0.1715
_refine_ls_goodness_of_fit_ref     0.856
_refine_ls_restrained_S_all     0.856
_refine_ls_number_reflns     5963
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0654P)²] 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     0.135
_refine_diff_density_min     -0.117
_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 (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT (Bruker, 2000)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXL-97 and PRPKAPPA (Ferguson, 1999)'
loop_
    _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
    _atom_site_type_symbol
    C1 0.2993(4) 0.44487(15) 0.4914(2) 0.0959(8) Uani d . 1 . . C
    O2 0.3503(2) 0.48398(12) 0.57345(16) 0.1263(7) Uani d . 1 . . O
    O1 0.3735(2) 0.43644(12) 0.40495(14) 0.1201(7) Uani d . 1 . . O
    C11 -0.2197(2) 0.28337(14) 0.68035(19) 0.0706(6) Uani d . 1 . . C
    C12 -0.1911(3) 0.22962(15) 0.7691(2) 0.0888(7) Uani d . 1 . . C
    C13 -0.2876(4) 0.16258(18) 0.7787(3) 0.1155(10) Uani d . 1 . . C
    C14 -0.4145(4) 0.1500(2) 0.7009(4) 0.1423(16) Uani d . 1 . . C
    C15 -0.4436(4) 0.2016(3) 0.6141(3) 0.1511(17) Uani d . 1 . . C
    C16 -0.3468(3) 0.2687(2) 0.6026(2) 0.1085(9) Uani d . 1 . . C
    C2 0.1439(4) 0.40161(15) 0.4777(2) 0.1028(8) Uani d . 1 . . C
    O3 0.0657(2) 0.41549(9) 0.57237(13) 0.1006(5) Uani d . 1 . . O
    N4 -0.0365(2) 0.34680(10) 0.58148(15) 0.0791(5) Uani d . 1 . . N
    C5 -0.1124(2) 0.35421(13) 0.66720(17) 0.0684(6) Uani d . 1 . . C
    C6 -0.0998(2) 0.42388(12) 0.74340(16) 0.0696(6) Uani d . 1 . . C
    C7 -0.1928(2) 0.43479(13) 0.82325(17) 0.0705(6) Uani d . 1 . . C
    C21 -0.1906(2) 0.50399(12) 0.90073(16) 0.0610(5) Uani d . 1 . . C
    C23 -0.1080(2) 0.64037(13) 0.96543(17) 0.0683(6) Uani d . 1 . . C
    C22 -0.1050(2) 0.57650(12) 0.89120(16) 0.0666(6) Uani d . 1 . . C
    C24 -0.1972(2) 0.63359(12) 1.05257(16) 0.0613(5) Uani d . 1 . . C
    O24 -0.19435(16) 0.70151(9) 1.12107(12) 0.0796(4) Uani d . 1 . . O
    C27 -0.2930(3) 0.70124(16) 1.20787(19) 0.0992(8) Uani d . 1 . . C
    C25 -0.2818(2) 0.56231(13) 1.06569(18) 0.0721(6) Uani d . 1 . . C
    C26 -0.2783(2) 0.49899(13) 0.98954(18) 0.0729(6) Uani d . 1 . . C
    H1 0.4532 0.4656 0.4119 0.180 Uiso calc R 1 . . H
    H12 -0.1056 0.2390 0.8227 0.107 Uiso calc R 1 . . H
    H13 -0.2668 0.1259 0.8379 0.139 Uiso calc R 1 . . H
    H4 -0.4816 0.1051 0.7081 0.171 Uiso calc R 1 . . H
    H15 -0.5299 0.1919 0.5613 0.181 Uiso calc R 1 . . H
    H16 -0.3676 0.3042 0.5421 0.130 Uiso calc R 1 . . H
    H2A 0.0797 0.4225 0.4122 0.123 Uiso calc R 1 . . H
    H2B 0.1597 0.3424 0.4680 0.123 Uiso calc R 1 . . H
    H6 -0.0220 0.4635 0.7363 0.084 Uiso calc R 1 . . H
    H7 -0.2676 0.3935 0.8302 0.085 Uiso calc R 1 . . H
    H23 -0.0497 0.6885 0.9571 0.082 Uiso calc R 1 . . H
    H22 -0.0441 0.5819 0.8329 0.080 Uiso calc R 1 . . H
    H27A -0.4013 0.6943 1.1769 0.149 Uiso calc R 1 . . H
    H27B -0.2815 0.7531 1.2474 0.149 Uiso calc R 1 . . H
    H27C -0.2629 0.6562 1.2578 0.149 Uiso calc R 1 . . H
    H25 -0.3407 0.5568 1.1251 0.087 Uiso calc R 1 . . H
    H26 -0.3371 0.4511 0.9981 0.087 Uiso calc R 1 . . H
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 . 1.214(3) no
    C1 O1 . 1.295(3) no
    C1 C2 . 1.486(4) no
    O1 H1 . 0.82 no
    C11 C16 . 1.370(3) no
    C11 C12 . 1.380(3) no
    C11 C5 . 1.479(3) no
    C12 C13 . 1.368(3) no
    C12 H12 . 0.93 no
    C13 C14 . 1.364(4) no
    C13 H13 . 0.93 no
    C14 C15 . 1.341(5) no
    C14 H4 . 0.93 no
    C15 C16 . 1.374(5) no
    C15 H15 . 0.93 no
    C16 H16 . 0.93 no
    C2 O3 . 1.414(3) no
    C2 H2A . 0.97 no
    C2 H2B . 0.97 no
    O3 N4 . 1.417(2) no
    N4 C5 . 1.294(2) no
    C5 C6 . 1.448(3) no
    C6 C7 . 1.335(3) no
    C6 H6 . 0.93 no
    C7 C21 . 1.455(3) no
    C7 H7 . 0.93 no
    C21 C26 . 1.385(3) no
    C21 C22 . 1.386(3) no
    C23 C22 . 1.368(3) no
    C23 C24 . 1.378(3) no
    C23 H23 . 0.93 no
    C22 H22 . 0.93 no
    C24 O24 . 1.370(2) no
    C24 C25 . 1.372(3) no
    O24 C27 . 1.424(2) no
    C27 H27A . 0.96 no
    C27 H27B . 0.96 no
    C27 H27C . 0.96 no
    C25 C26 . 1.377(3) no
    C25 H25 . 0.93 no
    C26 H26 . 0.93 no
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 . . 123.9(3) no
    O2 C1 C2 . . 124.2(2) no
    O1 C1 C2 . . 111.9(2) no
    C1 O1 H1 . . 109.5 no
    C16 C11 C12 . . 118.9(2) no
    C16 C11 C5 . . 120.3(2) no
    C12 C11 C5 . . 120.7(2) no
    C13 C12 C11 . . 120.5(3) no
    C13 C12 H12 . . 119.8 no
    C11 C12 H12 . . 119.8 no
    C14 C13 C12 . . 119.5(3) no
    C14 C13 H13 . . 120.3 no
    C12 C13 H13 . . 120.3 no
    C15 C14 C13 . . 120.7(3) no
    C15 C14 H4 . . 119.6 no
    C13 C14 H4 . . 119.6 no
    C14 C15 C16 . . 120.5(3) no
    C14 C15 H15 . . 119.7 no
    C16 C15 H15 . . 119.7 no
    C11 C16 C15 . . 119.9(3) no
    C11 C16 H16 . . 120.1 no
    C15 C16 H16 . . 120.1 no
    O3 C2 C1 . . 109.5(2) no
    O3 C2 H2A . . 109.8 no
    C1 C2 H2A . . 109.8 no
    O3 C2 H2B . . 109.8 no
    C1 C2 H2B . . 109.8 no
    H2A C2 H2B . . 108.2 no
    C2 O3 N4 . . 107.08(17) no
    C5 N4 O3 . . 111.16(17) no
    N4 C5 C6 . . 125.4(2) no
    N4 C5 C11 . . 112.94(18) no
    C6 C5 C11 . . 121.7(2) no
    C7 C6 C5 . . 124.1(2) no
    C7 C6 H6 . . 118.0 no
    C5 C6 H6 . . 118.0 no
    C6 C7 C21 . . 127.4(2) no
    C6 C7 H7 . . 116.3 no
    C21 C7 H7 . . 116.3 no
    C26 C21 C22 . . 116.82(18) no
    C26 C21 C7 . . 119.51(19) no
    C22 C21 C7 . . 123.67(19) no
    C22 C23 C24 . . 120.1(2) no
    C22 C23 H23 . . 119.9 no
    C24 C23 H23 . . 119.9 no
    C23 C22 C21 . . 121.60(19) no
    C23 C22 H22 . . 119.2 no
    C21 C22 H22 . . 119.2 no
    O24 C24 C25 . . 124.42(19) no
    O24 C24 C23 . . 115.57(19) no
    C25 C24 C23 . . 120.01(19) no
    C24 O24 C27 . . 118.53(17) no
    O24 C27 H27A . . 109.5 no
    O24 C27 H27B . . 109.5 no
    H27A C27 H27B . . 109.5 no
    O24 C27 H27C . . 109.5 no
    H27A C27 H27C . . 109.5 no
    H27B C27 H27C . . 109.5 no
    C24 C25 C26 . . 118.97(19) no
    C24 C25 H25 . . 120.5 no
    C26 C25 H25 . . 120.5 no
    C25 C26 C21 . . 122.5(2) no
    C25 C26 H26 . . 118.8 no
    C21 C26 H26 . . 118.8 no
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
    C16 C11 C12 C13 . . . . 0.4(3) ?
    C5 C11 C12 C13 . . . . -177.7(2) ?
    C11 C12 C13 C14 . . . . -1.2(4) ?
    C12 C13 C14 C15 . . . . 1.4(5) ?
    C13 C14 C15 C16 . . . . -0.7(6) ?
    C12 C11 C16 C15 . . . . 0.3(4) ?
    C5 C11 C16 C15 . . . . 178.4(2) ?
    C14 C15 C16 C11 . . . . -0.2(5) ?
    O2 C1 C2 O3 . . . . 1.7(4) ?
    O1 C1 C2 O3 . . . . -177.8(2) ?
    C1 C2 O3 N4 . . . . -153.09(19) ?
    C2 O3 N4 C5 . . . . 179.48(19) ?
    O3 N4 C5 C6 . . . . 1.5(3) ?
    O3 N4 C5 C11 . . . . -179.55(17) ?
    C16 C11 C5 N4 . . . . -64.8(2) ?
    C12 C11 C5 N4 . . . . 113.3(2) ?
    C16 C11 C5 C6 . . . . 114.2(2) ?
    C12 C11 C5 C6 . . . . -67.7(3) ?
    N4 C5 C6 C7 . . . . 171.67(19) ?
    C11 C5 C6 C7 . . . . -7.2(3) ?
    C5 C6 C7 C21 . . . . -178.12(18) ?
    C6 C7 C21 C26 . . . . -169.78(19) ?
    C6 C7 C21 C22 . . . . 10.5(3) ?
    C24 C23 C22 C21 . . . . 0.2(3) ?
    C26 C21 C22 C23 . . . . -0.5(3) ?
    C7 C21 C22 C23 . . . . 179.23(18) ?
    C22 C23 C24 O24 . . . . -178.90(17) ?
    C22 C23 C24 C25 . . . . 0.7(3) ?
    C25 C24 O24 C27 . . . . -4.2(3) ?
    C23 C24 O24 C27 . . . . 175.38(17) ?
    O24 C24 C25 C26 . . . . 178.34(18) ?
    C23 C24 C25 C26 . . . . -1.2(3) ?
    C24 C25 C26 C21 . . . . 0.9(3) ?
    C22 C21 C26 C25 . . . . -0.1(3) ?
    C7 C21 C26 C25 . . . . -179.80(19) ?
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
    O1 H1 O2 3_666 0.82 1.85 2.662(3) 171 y
data_IIa
_chemical_name_systematic
;
(E)-[1-(4-methoxyphenyl)-3-phenyl-2-propenylideneamino)oxyacetic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H17 N O4'
_chemical_formula_sum     'C18 H17 N O4'
_chemical_formula_weight     311.33
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x, -y+1/2, z+1/2'
    '-x, -y, -z'
    '-x, y-1/2, -z-1/2'
_cell_length_a     6.4499(2)
_cell_length_b     14.9693(5)
_cell_length_c     16.6559(6)
_cell_angle_alpha     90.00
_cell_angle_beta     92.947(2)
_cell_angle_gamma     90.00
_cell_volume     1606.01(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3690
_cell_measurement_theta_min     2.98
_cell_measurement_theta_max     27.52
_cell_measurement_temperature     120(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.288
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     656
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     'SORTAV (Blessing 1995 and 1997'
_exptl_absorpt_correction_T_min     0.967
_exptl_absorpt_correction_T_max     0.995
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Kappa-CCD'
_diffrn_measurement_method     'φ scans, and ω scans with κ offsets'
_diffrn_reflns_number     17758
_diffrn_reflns_av_R_equivalents     0.0619
_diffrn_reflns_av_sigmaI/netI     0.0440
_diffrn_reflns_theta_min     2.98
_diffrn_reflns_theta_max     27.52
_diffrn_reflns_theta_full     27.52
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     16
_diffrn_standards_decay_%     negligible
_reflns_number_total     3690
_reflns_number_gt     2647
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0968
_refine_ls_R_factor_gt     0.0578
_refine_ls_wR_factor_gt     0.1835
_refine_ls_wR_factor_ref     0.2318
_refine_ls_goodness_of_fit_ref     1.136
_refine_ls_restrained_S_all     1.136
_refine_ls_number_reflns     3690
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.1318P)²+0.4171P] 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     0.656
_refine_diff_density_min     -0.639
_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     'Kappa-CCD server software (Nonius, 1997)'
_computing_cell_refinement     'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO-SMN'
_computing_structure_solution
                       'OSCAIL (McArdle , 2003) and SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement     'OSCAIL and SHELXS-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXL-97 and PRPKAPPA (Ferguson, 1999)'
loop_
    _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
    _atom_site_type_symbol
    C1 0.5113(3) 0.56573(15) 0.40172(15) 0.0304(5) Uani d . 1 . . C
    O2 0.3533(2) 0.52726(11) 0.41955(11) 0.0350(4) Uani d . 1 . . O
    O1 0.6769(2) 0.57544(12) 0.45065(11) 0.0352(4) Uani d . 1 . . O
    C11 0.0796(4) 0.43697(15) 0.16447(15) 0.0311(5) Uani d . 1 . . C
    C12 -0.1059(4) 0.39619(16) 0.18352(17) 0.0367(6) Uani d . 1 . . C
    C13 -0.1517(4) 0.30945(16) 0.15832(19) 0.0433(7) Uani d . 1 . . C
    C14 -0.0143(5) 0.26405(18) 0.11227(17) 0.0482(8) Uani d . 1 . . C
    C15 0.1672(5) 0.30496(18) 0.09115(17) 0.0467(7) Uani d . 1 . . C
    C16 0.2164(4) 0.39095(17) 0.11727(17) 0.0401(6) Uani d . 1 . . C
    C2 0.5414(4) 0.60708(16) 0.32101(16) 0.0336(6) Uani d . 1 . . C
    O3 0.3571(2) 0.61316(10) 0.27205(11) 0.0336(4) Uani d . 1 . . O
    N4 0.3144(3) 0.52776(12) 0.23787(13) 0.0310(5) Uani d . 1 . . N
    C5 0.1352(4) 0.52637(15) 0.19887(15) 0.0296(5) Uani d . 1 . . C
    C6 -0.0067(4) 0.60192(15) 0.19205(15) 0.0299(5) Uani d . 1 . . C
    C7 -0.1762(4) 0.60633(15) 0.14176(15) 0.0302(5) Uani d . 1 . . C
    C21 -0.3231(3) 0.68066(15) 0.13578(14) 0.0287(5) Uani d . 1 . . C
    C26 -0.4999(4) 0.67479(15) 0.08457(15) 0.0321(6) Uani d . 1 . . C
    C25 -0.6458(4) 0.74346(16) 0.07875(15) 0.0338(6) Uani d . 1 . . C
    C24 -0.6148(4) 0.81959(15) 0.12510(15) 0.0301(5) Uani d . 1 . . C
    O24 -0.7452(3) 0.89141(11) 0.12568(11) 0.0390(5) Uani d . 1 . . O
    C27 -0.9303(4) 0.88886(19) 0.07543(18) 0.0414(7) Uani d . 1 . . C
    C23 -0.4387(4) 0.82659(15) 0.17666(16) 0.0334(6) Uani d . 1 . . C
    C22 -0.2960(4) 0.75869(15) 0.18168(15) 0.0308(5) Uani d . 1 . . C
    H1 0.6613 0.5462 0.4930 0.053 Uiso calc R 1 . . H
    H12 -0.2021 0.4280 0.2141 0.044 Uiso calc R 1 . . H
    H13 -0.2768 0.2816 0.1727 0.052 Uiso calc R 1 . . H
    H14 -0.0445 0.2047 0.0951 0.058 Uiso calc R 1 . . H
    H15 0.2595 0.2739 0.0584 0.056 Uiso calc R 1 . . H
    H16 0.3424 0.4182 0.1030 0.048 Uiso calc R 1 . . H
    H2A 0.5998 0.6678 0.3291 0.040 Uiso calc R 1 . . H
    H2B 0.6438 0.5712 0.2927 0.040 Uiso calc R 1 . . H
    H6 0.0228 0.6520 0.2258 0.036 Uiso calc R 1 . . H
    H7 -0.2029 0.5568 0.1071 0.036 Uiso calc R 1 . . H
    H26 -0.5218 0.6226 0.0528 0.039 Uiso calc R 1 . . H
    H25 -0.7653 0.7381 0.0433 0.041 Uiso calc R 1 . . H
    H27A -0.8948 0.8910 0.0190 0.062 Uiso calc R 1 . . H
    H27B -1.0175 0.9403 0.0873 0.062 Uiso calc R 1 . . H
    H27C -1.0061 0.8336 0.0854 0.062 Uiso calc R 1 . . H
    H23 -0.4172 0.8787 0.2085 0.040 Uiso calc R 1 . . H
    H22 -0.1763 0.7646 0.2170 0.037 Uiso calc R 1 . . H
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 . 1.221(3) no
    C1 O1 . 1.318(3) no
    C1 C2 . 1.501(4) no
    O1 H1 . 0.84 no
    C11 C16 . 1.394(4) no
    C11 C12 . 1.394(3) no
    C11 C5 . 1.492(3) no
    C12 C13 . 1.392(3) no
    C12 H12 . 0.95 no
    C13 C14 . 1.380(4) no
    C13 H13 . 0.95 no
    C14 C15 . 1.383(4) no
    C14 H14 . 0.95 no
    C15 C16 . 1.390(4) no
    C15 H15 . 0.95 no
    C16 H16 . 0.95 no
    C2 O3 . 1.409(3) no
    C2 H2A . 0.99 no
    C2 H2B . 0.99 no
    O3 N4 . 1.421(2) no
    N4 C5 . 1.297(3) no
    C5 C6 . 1.456(3) no
    C6 C7 . 1.344(3) no
    C6 H6 . 0.95 no
    C7 C21 . 1.461(3) no
    C7 H7 . 0.95 no
    C21 C26 . 1.391(3) no
    C21 C22 . 1.402(3) no
    C26 C25 . 1.393(3) no
    C26 H26 . 0.95 no
    C25 C24 . 1.385(3) no
    C25 H25 . 0.95 no
    C24 O24 . 1.365(3) no
    C24 C23 . 1.393(3) no
    O24 C27 . 1.423(3) no
    C27 H27A . 0.98 no
    C27 H27B . 0.98 no
    C27 H27C . 0.98 no
    C23 C22 . 1.371(3) no
    C23 H23 . 0.95 no
    C22 H22 . 0.95 no
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 . . 124.2(2) no
    O2 C1 C2 . . 124.1(2) no
    O1 C1 C2 . . 111.76(19) no
    C1 O1 H1 . . 109.5 no
    C16 C11 C12 . . 119.2(2) no
    C16 C11 C5 . . 120.9(2) no
    C12 C11 C5 . . 119.8(2) no
    C13 C12 C11 . . 120.7(3) no
    C13 C12 H12 . . 119.6 no
    C11 C12 H12 . . 119.6 no
    C14 C13 C12 . . 119.7(3) no
    C14 C13 H13 . . 120.2 no
    C12 C13 H13 . . 120.2 no
    C13 C14 C15 . . 120.0(3) no
    C13 C14 H14 . . 120.0 no
    C15 C14 H14 . . 120.0 no
    C14 C15 C16 . . 120.9(3) no
    C14 C15 H15 . . 119.6 no
    C16 C15 H15 . . 119.6 no
    C15 C16 C11 . . 119.6(3) no
    C15 C16 H16 . . 120.2 no
    C11 C16 H16 . . 120.2 no
    O3 C2 C1 . . 113.64(19) no
    O3 C2 H2A . . 108.8 no
    C1 C2 H2A . . 108.8 no
    O3 C2 H2B . . 108.8 no
    C1 C2 H2B . . 108.8 no
    H2A C2 H2B . . 107.7 no
    C2 O3 N4 . . 108.30(16) no
    C5 N4 O3 . . 111.37(17) no
    N4 C5 C6 . . 124.6(2) no
    N4 C5 C11 . . 113.41(19) no
    C6 C5 C11 . . 121.9(2) no
    C7 C6 C5 . . 125.1(2) no
    C7 C6 H6 . . 117.5 no
    C5 C6 H6 . . 117.5 no
    C6 C7 C21 . . 125.7(2) no
    C6 C7 H7 . . 117.2 no
    C21 C7 H7 . . 117.2 no
    C26 C21 C22 . . 117.5(2) no
    C26 C21 C7 . . 120.1(2) no
    C22 C21 C7 . . 122.4(2) no
    C21 C26 C25 . . 121.7(2) no
    C21 C26 H26 . . 119.2 no
    C25 C26 H26 . . 119.2 no
    C24 C25 C26 . . 119.4(2) no
    C24 C25 H25 . . 120.3 no
    C26 C25 H25 . . 120.3 no
    O24 C24 C25 . . 125.5(2) no
    O24 C24 C23 . . 114.8(2) no
    C25 C24 C23 . . 119.7(2) no
    C24 O24 C27 . . 118.25(19) no
    O24 C27 H27A . . 109.5 no
    O24 C27 H27B . . 109.5 no
    H27A C27 H27B . . 109.5 no
    O24 C27 H27C . . 109.5 no
    H27A C27 H27C . . 109.5 no
    H27B C27 H27C . . 109.5 no
    C22 C23 C24 . . 120.4(2) no
    C22 C23 H23 . . 119.8 no
    C24 C23 H23 . . 119.8 no
    C23 C22 C21 . . 121.3(2) no
    C23 C22 H22 . . 119.3 no
    C21 C22 H22 . . 119.3 no
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
    C16 C11 C12 C13 . . . . 2.2(4) no
    C5 C11 C12 C13 . . . . -173.9(2) no
    C11 C12 C13 C14 . . . . -1.6(4) no
    C12 C13 C14 C15 . . . . -0.3(4) no
    C13 C14 C15 C16 . . . . 1.5(4) no
    C14 C15 C16 C11 . . . . -0.9(4) no
    C12 C11 C16 C15 . . . . -1.0(4) no
    C5 C11 C16 C15 . . . . 175.1(2) no
    O2 C1 C2 O3 . . . . 11.7(3) no
    O1 C1 C2 O3 . . . . -168.81(19) no
    C1 C2 O3 N4 . . . . -78.8(2) no
    C2 O3 N4 C5 . . . . 173.23(19) no
    O3 N4 C5 C6 . . . . -1.1(3) no
    O3 N4 C5 C11 . . . . -177.76(18) no
    C16 C11 C5 N4 . . . . -51.8(3) no
    C12 C11 C5 N4 . . . . 124.3(2) no
    C16 C11 C5 C6 . . . . 131.5(3) no
    C12 C11 C5 C6 . . . . -52.4(3) no
    N4 C5 C6 C7 . . . . 168.7(2) no
    C11 C5 C6 C7 . . . . -14.9(4) no
    C5 C6 C7 C21 . . . . 178.3(2) no
    C6 C7 C21 C26 . . . . -176.1(2) no
    C6 C7 C21 C22 . . . . 2.4(4) no
    C22 C21 C26 C25 . . . . -0.1(3) no
    C7 C21 C26 C25 . . . . 178.5(2) no
    C21 C26 C25 C24 . . . . -0.1(4) no
    C26 C25 C24 O24 . . . . -179.6(2) no
    C26 C25 C24 C23 . . . . 0.1(4) no
    C25 C24 O24 C27 . . . . 0.6(4) no
    C23 C24 O24 C27 . . . . -179.1(2) no
    O24 C24 C23 C22 . . . . 179.8(2) no
    C25 C24 C23 C22 . . . . 0.1(4) no
    C24 C23 C22 C21 . . . . -0.3(4) no
    C26 C21 C22 C23 . . . . 0.3(4) no
    C7 C21 C22 C23 . . . . -178.2(2) no
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
    O1 H1 O2 3_666 0.84 1.83 2.668(2) 174 y
    C23 H23 N4 4_566 0.95 2.48 3.409(3) 166 y
    C22 H22 Cg1 4_566 0.95 2.85 3.647(3) 142 y
data_IIb
_chemical_name_systematic
;
(E)-[1-(4-methoxyphenyl)-3-phenyl-2-propenylideneamino)oxyacetic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H17 N O4'
_chemical_formula_sum     'C18 H17 N O4'
_chemical_formula_weight     311.33
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y+1/2, z+1/2'
_cell_length_a     6.4238(3)
_cell_length_b     15.1513(9)
_cell_length_c     17.0552(9)
_cell_angle_alpha     90.00
_cell_angle_beta     93.167(2)
_cell_angle_gamma     90.00
_cell_volume     1657.43(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3837
_cell_measurement_theta_min     1.80
_cell_measurement_theta_max     27.55
_cell_measurement_temperature     291(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.248
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     656
_exptl_absorpt_coefficient_mu     0.089
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.982
_exptl_absorpt_correction_T_max     0.996
_exptl_special_details
;
?
;
_diffrn_ambient_temperature     291(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method     φ-ω
_diffrn_reflns_number     13953
_diffrn_reflns_av_R_equivalents     0.0382
_diffrn_reflns_av_sigmaI/netI     0.0326
_diffrn_reflns_theta_min     1.80
_diffrn_reflns_theta_max     27.55
_diffrn_reflns_theta_full     27.55
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     21
_diffrn_standards_decay_%     negligible
_reflns_number_total     3837
_reflns_number_gt     2171
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0931
_refine_ls_R_factor_gt     0.0490
_refine_ls_wR_factor_gt     0.1360
_refine_ls_wR_factor_ref     0.1513
_refine_ls_goodness_of_fit_ref     0.984
_refine_ls_restrained_S_all     0.984
_refine_ls_number_reflns     3837
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0795P)²+0.0527P] 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     0.152
_refine_diff_density_min     -0.137
_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 (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT (Bruker, 2000)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ' PLATON (Spek, 2003)'
_computing_publication_material     'SHELXL-97 and PRPKAPPA (Ferguson, 1999)'
loop_
    _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
    _atom_site_type_symbol
    O1 0.6749(2) 0.57149(10) 0.44883(8) 0.0731(4) Uani d . 1 . . O
    O2 0.35075(19) 0.52460(10) 0.42022(8) 0.0715(4) Uani d . 1 . . O
    O3 0.35183(19) 0.60586(8) 0.27465(8) 0.0655(4) Uani d . 1 . . O
    O24 -0.7423(2) 0.88371(10) 0.12369(9) 0.0827(5) Uani d . 1 . . O
    N4 0.3106(2) 0.52168(9) 0.24115(9) 0.0589(4) Uani d . 1 . . N
    C1 0.5087(3) 0.56167(12) 0.40199(11) 0.0576(5) Uani d . 1 . . C
    C2 0.5374(3) 0.60012(13) 0.32253(12) 0.0638(5) Uani d . 1 . . C
    C5 0.1331(3) 0.52079(11) 0.20183(10) 0.0549(4) Uani d . 1 . . C
    C6 -0.0105(3) 0.59500(11) 0.19403(11) 0.0575(4) Uani d . 1 . . C
    C7 -0.1774(3) 0.59977(12) 0.14494(11) 0.0576(4) Uani d . 1 . . C
    C11 0.0793(3) 0.43272(12) 0.16713(11) 0.0595(5) Uani d . 1 . . C
    C12 -0.1032(3) 0.39073(13) 0.18608(13) 0.0733(6) Uani d . 1 . . C
    C13 -0.1463(4) 0.30646(15) 0.15944(16) 0.0896(7) Uani d . 1 . . C
    C14 -0.0131(5) 0.26365(17) 0.11396(15) 0.0972(9) Uani d . 1 . . C
    C15 0.1652(5) 0.30432(17) 0.09294(14) 0.0970(8) Uani d . 1 . . C
    C16 0.2143(4) 0.38905(14) 0.12045(13) 0.0788(6) Uani d . 1 . . C
    C21 -0.3237(3) 0.67349(11) 0.13728(10) 0.0536(4) Uani d . 1 . . C
    C22 -0.2960(3) 0.75123(12) 0.18074(11) 0.0622(5) Uani d . 1 . . C
    C23 -0.4369(3) 0.81881(12) 0.17438(12) 0.0670(5) Uani d . 1 . . C
    C24 -0.6123(3) 0.81232(13) 0.12425(11) 0.0614(5) Uani d . 1 . . C
    C27 -0.9292(3) 0.88148(17) 0.07492(15) 0.0883(7) Uani d . 1 . . C
    C25 -0.6452(3) 0.73650(14) 0.08002(12) 0.0674(5) Uani d . 1 . . C
    C26 -0.4998(3) 0.66828(13) 0.08728(11) 0.0651(5) Uani d . 1 . . C
    H1 0.6609 0.5435 0.4894 0.110 Uiso calc R 1 . . H
    H2A 0.5964 0.6588 0.3289 0.077 Uiso calc R 1 . . H
    H2B 0.6368 0.5642 0.2960 0.077 Uiso calc R 1 . . H
    H12 -0.1969 0.4196 0.2169 0.088 Uiso calc R 1 . . H
    H13 -0.2684 0.2787 0.1729 0.108 Uiso calc R 1 . . H
    H14 -0.0430 0.2065 0.0970 0.117 Uiso calc R 1 . . H
    H15 0.2542 0.2755 0.0602 0.116 Uiso calc R 1 . . H
    H16 0.3378 0.4159 0.1073 0.095 Uiso calc R 1 . . H
    H6 0.0175 0.6434 0.2264 0.069 Uiso calc R 1 . . H
    H7 -0.2040 0.5515 0.1122 0.069 Uiso calc R 1 . . H
    H22 -0.1788 0.7571 0.2148 0.075 Uiso calc R 1 . . H
    H23 -0.4143 0.8697 0.2042 0.080 Uiso calc R 1 . . H
    H27A -0.8953 0.8811 0.0208 0.132 Uiso calc R 1 . . H
    H27B -1.0118 0.9326 0.0850 0.132 Uiso calc R 1 . . H
    H27C -1.0066 0.8292 0.0861 0.132 Uiso calc R 1 . . H
    H25 -0.7626 0.7312 0.0459 0.081 Uiso calc R 1 . . H
    H26 -0.5223 0.6175 0.0574 0.078 Uiso calc R 1 . . H
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 . 1.215(2) no
    C1 O1 . 1.306(2) no
    C1 C2 . 1.496(3) no
    O1 H1 . 0.82 no
    C2 O3 . 1.410(2) no
    C2 H2A . 0.97 no
    C2 H2B . 0.97 no
    O3 N4 . 1.4165(18) no
    N4 C5 . 1.291(2) no
    C5 C6 . 1.456(2) no
    C5 C11 . 1.493(2) no
    C11 C16 . 1.379(3) no
    C11 C12 . 1.387(3) no
    C12 C13 . 1.378(3) no
    C12 H12 . 0.93 no
    C13 C14 . 1.352(4) no
    C13 H13 . 0.93 no
    C14 C15 . 1.366(4) no
    C14 H14 . 0.93 no
    C15 C16 . 1.397(3) no
    C15 H15 . 0.93 no
    C16 H16 . 0.93 no
    C6 C7 . 1.326(2) no
    C6 H6 . 0.93 no
    C7 C21 . 1.461(2) no
    C7 H7 . 0.93 no
    C21 C26 . 1.381(2) no
    C21 C22 . 1.398(2) no
    C22 C23 . 1.367(2) no
    C22 H22 . 0.93 no
    C23 C24 . 1.380(2) no
    C23 H23 . 0.93 no
    C24 O24 . 1.366(2) no
    C24 C25 . 1.384(3) no
    O24 C27 . 1.423(2) no
    C27 H27A . 0.96 no
    C27 H27B . 0.96 no
    C27 H27C . 0.96 no
    C25 C26 . 1.394(3) no
    C25 H25 . 0.93 no
    C26 H26 . 0.93 no
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 . . 124.19(17) no
    O2 C1 C2 . . 123.94(16) no
    O1 C1 C2 . . 111.86(15) no
    C1 O1 H1 . . 109.5 no
    O3 C2 C1 . . 113.97(15) no
    O3 C2 H2A . . 108.8 no
    C1 C2 H2A . . 108.8 no
    O3 C2 H2B . . 108.8 no
    C1 C2 H2B . . 108.8 no
    H2A C2 H2B . . 107.7 no
    C2 O3 N4 . . 108.14(13) no
    C5 N4 O3 . . 111.05(14) no
    N4 C5 C6 . . 125.21(16) no
    N4 C5 C11 . . 113.21(15) no
    C6 C5 C11 . . 121.50(16) no
    C16 C11 C12 . . 118.76(19) no
    C16 C11 C5 . . 121.23(19) no
    C12 C11 C5 . . 119.86(18) no
    C13 C12 C11 . . 120.3(2) no
    C13 C12 H12 . . 119.8 no
    C11 C12 H12 . . 119.8 no
    C14 C13 C12 . . 120.8(2) no
    C14 C13 H13 . . 119.6 no
    C12 C13 H13 . . 119.6 no
    C13 C14 C15 . . 120.0(2) no
    C13 C14 H14 . . 120.0 no
    C15 C14 H14 . . 120.0 no
    C14 C15 C16 . . 120.2(2) no
    C14 C15 H15 . . 119.9 no
    C16 C15 H15 . . 119.9 no
    C11 C16 C15 . . 119.8(2) no
    C11 C16 H16 . . 120.1 no
    C15 C16 H16 . . 120.1 no
    C7 C6 C5 . . 125.89(17) no
    C7 C6 H6 . . 117.1 no
    C5 C6 H6 . . 117.1 no
    C6 C7 C21 . . 126.31(17) no
    C6 C7 H7 . . 116.8 no
    C21 C7 H7 . . 116.8 no
    C26 C21 C22 . . 116.85(16) no
    C26 C21 C7 . . 120.83(16) no
    C22 C21 C7 . . 122.31(15) no
    C23 C22 C21 . . 121.65(16) no
    C23 C22 H22 . . 119.2 no
    C21 C22 H22 . . 119.2 no
    C22 C23 C24 . . 120.68(17) no
    C22 C23 H23 . . 119.7 no
    C24 C23 H23 . . 119.7 no
    O24 C24 C23 . . 115.22(17) no
    O24 C24 C25 . . 125.32(17) no
    C23 C24 C25 . . 119.46(17) no
    C24 O24 C27 . . 118.77(17) no
    O24 C27 H27A . . 109.5 no
    O24 C27 H27B . . 109.5 no
    H27A C27 H27B . . 109.5 no
    O24 C27 H27C . . 109.5 no
    H27A C27 H27C . . 109.5 no
    H27B C27 H27C . . 109.5 no
    C24 C25 C26 . . 119.05(17) no
    C24 C25 H25 . . 120.5 no
    C26 C25 H25 . . 120.5 no
    C21 C26 C25 . . 122.30(18) no
    C21 C26 H26 . . 118.8 no
    C25 C26 H26 . . 118.8 no
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 O3 . . . . 12.1(3) no
    O1 C1 C2 O3 . . . . -168.96(16) no
    C1 C2 O3 N4 . . . . -80.63(18) no
    C2 O3 N4 C5 . . . . 174.60(15) no
    O3 N4 C5 C6 . . . . -1.6(2) no
    O3 N4 C5 C11 . . . . -178.36(14) no
    N4 C5 C11 C16 . . . . -53.7(2) no
    C6 C5 C11 C16 . . . . 129.4(2) no
    N4 C5 C11 C12 . . . . 121.89(19) no
    C6 C5 C11 C12 . . . . -55.0(2) no
    C16 C11 C12 C13 . . . . 0.9(3) no
    C5 C11 C12 C13 . . . . -174.80(19) no
    C11 C12 C13 C14 . . . . -0.6(3) no
    C12 C13 C14 C15 . . . . -0.9(4) no
    C13 C14 C15 C16 . . . . 2.2(4) no
    C12 C11 C16 C15 . . . . 0.3(3) no
    C5 C11 C16 C15 . . . . 176.0(2) no
    C14 C15 C16 C11 . . . . -1.9(3) no
    N4 C5 C6 C7 . . . . 169.29(17) no
    C11 C5 C6 C7 . . . . -14.2(3) no
    C5 C6 C7 C21 . . . . 179.27(16) no
    C6 C7 C21 C26 . . . . -175.84(18) no
    C6 C7 C21 C22 . . . . 2.8(3) no
    C26 C21 C22 C23 . . . . 0.3(3) no
    C7 C21 C22 C23 . . . . -178.36(17) no
    C21 C22 C23 C24 . . . . -0.1(3) no
    C22 C23 C24 O24 . . . . 179.32(17) no
    C22 C23 C24 C25 . . . . 0.0(3) no
    C23 C24 O24 C27 . . . . -178.57(18) no
    C25 C24 O24 C27 . . . . 0.8(3) no
    O24 C24 C25 C26 . . . . -179.26(18) no
    C23 C24 C25 C26 . . . . 0.0(3) no
    C22 C21 C26 C25 . . . . -0.3(3) no
    C7 C21 C26 C25 . . . . 178.38(17) no
    C24 C25 C26 C21 . . . . 0.1(3) no
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
    O1 H1 O2 3_666 0.82 1.86 2.679(2) 175 y
    C23 H23 N4 2_555 0.93 2.56 3.472(2) 167 y
    C22 H22 Cg1 2_555 0.93 2.94 3.712(2) 141 y
data_III
_chemical_name_systematic
;
(E)-[1-(4-methoxyphenyl)-3-phenyl-2-propenylideneamino)oxyacetic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H17 N O4'
_chemical_formula_sum     'C18 H17 N O4'
_chemical_formula_weight     311.33
_chemical_melting_point     ?
_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     12.1552(4)
_cell_length_b     15.8657(4)
_cell_length_c     16.6708(5)
_cell_angle_alpha     90.00
_cell_angle_beta     97.4250(15)
_cell_angle_gamma     90.00
_cell_volume     3188.02(16)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     7291
_cell_measurement_theta_min     3.07
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     120(2)
_exptl_crystal_description     lath
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.297
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1312
_exptl_absorpt_coefficient_mu     0.092
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     'SADABS V2.10 (Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.950
_exptl_absorpt_correction_T_max     0.991
_exptl_special_details
;
?
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type
                                 'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method     'φ & ω scans'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     37246
_diffrn_reflns_av_R_equivalents     0.0604
_diffrn_reflns_av_sigmaI/netI     0.0558
_diffrn_reflns_theta_min     3.07
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_decay_%     negligible
_reflns_number_total     7291
_reflns_number_gt     4714
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0923
_refine_ls_R_factor_gt     0.0480
_refine_ls_wR_factor_gt     0.1120
_refine_ls_wR_factor_ref     0.1329
_refine_ls_goodness_of_fit_ref     1.031
_refine_ls_restrained_S_all     1.031
_refine_ls_number_reflns     7291
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0728P)²+0.0298P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.192
_refine_diff_density_min     -0.270
_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     'COLLECT (Hooft, 1999)'
_computing_cell_refinement     'DENZO (Otwinowski & Minor, 1997) & COLLECT'
_computing_data_reduction     'DENZO & COLLECT '
_computing_structure_solution
                        'OSCAIL (McArdle, 2003) and SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement     'OSCAIL and SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXL-97 and PRPKAPPA (Ferguson, 1999)'
loop_
    _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
    _atom_site_type_symbol
    O11 0.60212(10) 0.56379(9) 0.28717(7) 0.0435(4) Uani d . 1 . . O
    O12 0.42927(11) 0.52190(8) 0.29603(7) 0.0411(3) Uani d . 1 . . O
    O13 0.43379(10) 0.58474(7) 0.44360(7) 0.0323(3) Uani d . 1 . . O
    O124 -0.11867(10) 0.29543(7) 0.59410(7) 0.0331(3) Uani d . 1 . . O
    N14 0.42907(12) 0.64910(9) 0.50237(8) 0.0290(3) Uani d . 1 . . N
    C11 0.51295(14) 0.55789(11) 0.32369(10) 0.0291(4) Uani d . 1 . . C
    C12 0.52739(15) 0.60170(12) 0.40365(11) 0.0352(4) Uani d . 1 . . C
    C15 0.34766(14) 0.63659(10) 0.54340(9) 0.0264(4) Uani d . 1 . . C
    C16 0.26956(14) 0.56694(10) 0.53505(9) 0.0280(4) Uani d . 1 . . C
    C17 0.19449(14) 0.55516(10) 0.58655(10) 0.0281(4) Uani d . 1 . . C
    C111 0.33781(14) 0.70341(10) 0.60582(9) 0.0269(4) Uani d . 1 . . C
    C112 0.25273(17) 0.76212(12) 0.59476(11) 0.0409(5) Uani d . 1 . . C
    C113 0.24311(18) 0.82324(12) 0.65273(11) 0.0444(5) Uani d . 1 . . C
    C114 0.31780(16) 0.82537(11) 0.72226(11) 0.0365(4) Uani d . 1 . . C
    C115 0.40130(15) 0.76687(12) 0.73392(11) 0.0391(5) Uani d . 1 . . C
    C116 0.41229(14) 0.70639(12) 0.67570(10) 0.0348(4) Uani d . 1 . . C
    C121 0.11332(14) 0.48772(10) 0.58652(9) 0.0269(4) Uani d . 1 . . C
    C122 0.11024(14) 0.41659(10) 0.53648(9) 0.0280(4) Uani d . 1 . . C
    C123 0.03236(14) 0.35489(10) 0.54017(10) 0.0290(4) Uani d . 1 . . C
    C124 -0.04624(14) 0.36190(10) 0.59366(9) 0.0268(4) Uani d . 1 . . C
    C127 -0.19932(15) 0.29812(13) 0.64951(11) 0.0388(4) Uani d . 1 . . C
    C125 -0.04615(14) 0.43180(10) 0.64316(10) 0.0290(4) Uani d . 1 . . C
    C126 0.03363(14) 0.49315(10) 0.63944(10) 0.0303(4) Uani d . 1 . . C
    O21 0.40174(10) 0.43730(8) 0.15846(7) 0.0350(3) Uani d . 1 . . O
    O22 0.57373(10) 0.48298(8) 0.14661(7) 0.0344(3) Uani d . 1 . . O
    O23 0.56570(9) 0.41308(7) -0.00042(7) 0.0292(3) Uani d . 1 . . O
    O224 1.13190(9) 0.69604(7) -0.09055(7) 0.0304(3) Uani d . 1 . . O
    N24 0.58213(11) 0.33839(8) -0.04476(8) 0.0258(3) Uani d . 1 . . N
    C21 0.48979(14) 0.44498(10) 0.12040(10) 0.0276(4) Uani d . 1 . . C
    C22 0.47239(14) 0.39976(10) 0.04122(10) 0.0285(4) Uani d . 1 . . C
    C25 0.67422(13) 0.34212(10) -0.07630(9) 0.0232(3) Uani d . 1 . . C
    C26 0.75050(13) 0.41265(10) -0.06827(9) 0.0247(4) Uani d . 1 . . C
    C27 0.83773(13) 0.42128(10) -0.10911(9) 0.0244(4) Uani d . 1 . . C
    C211 0.69586(13) 0.26371(10) -0.12096(9) 0.0234(4) Uani d . 1 . . C
    C212 0.78964(14) 0.21562(10) -0.09741(10) 0.0272(4) Uani d . 1 . . C
    C213 0.80524(14) 0.13922(10) -0.13449(10) 0.0305(4) Uani d . 1 . . C
    C214 0.72783(15) 0.11144(11) -0.19686(10) 0.0330(4) Uani d . 1 . . C
    C215 0.63508(15) 0.15915(11) -0.22151(10) 0.0342(4) Uani d . 1 . . C
    C216 0.61770(14) 0.23510(11) -0.18340(10) 0.0296(4) Uani d . 1 . . C
    C221 0.91380(13) 0.49278(10) -0.10393(9) 0.0234(4) Uani d . 1 . . C
    C222 0.89385(13) 0.56883(10) -0.06499(9) 0.0254(4) Uani d . 1 . . C
    C223 0.96769(14) 0.63421(10) -0.06110(9) 0.0263(4) Uani d . 1 . . C
    C224 1.06506(13) 0.62654(10) -0.09646(9) 0.0246(4) Uani d . 1 . . C
    C227 1.22717(15) 0.69469(12) -0.13253(11) 0.0374(4) Uani d . 1 . . C
    C225 1.08826(13) 0.55199(10) -0.13456(9) 0.0261(4) Uani d . 1 . . C
    C226 1.01226(13) 0.48678(10) -0.13817(9) 0.0255(4) Uani d . 1 . . C
    H11 0.5911 0.5390 0.2423 0.065 Uiso calc R 1 . . H
    H12A 0.5956 0.5814 0.4369 0.042 Uiso calc R 1 . . H
    H12B 0.5346 0.6632 0.3957 0.042 Uiso calc R 1 . . H
    H112 0.2007 0.7604 0.5471 0.049 Uiso calc R 1 . . H
    H113 0.1851 0.8636 0.6446 0.053 Uiso calc R 1 . . H
    H114 0.3115 0.8673 0.7621 0.044 Uiso calc R 1 . . H
    H115 0.4520 0.7679 0.7823 0.047 Uiso calc R 1 . . H
    H116 0.4713 0.6668 0.6838 0.042 Uiso calc R 1 . . H
    H16 0.2716 0.5283 0.4917 0.034 Uiso calc R 1 . . H
    H17 0.1944 0.5960 0.6282 0.034 Uiso calc R 1 . . H
    H122 0.1630 0.4111 0.4994 0.034 Uiso calc R 1 . . H
    H123 0.0319 0.3069 0.5060 0.035 Uiso calc R 1 . . H
    H12C -0.2455 0.3485 0.6390 0.058 Uiso calc R 1 . . H
    H12D -0.1614 0.2999 0.7051 0.058 Uiso calc R 1 . . H
    H12E -0.2462 0.2477 0.6424 0.058 Uiso calc R 1 . . H
    H125 -0.1002 0.4376 0.6792 0.035 Uiso calc R 1 . . H
    H126 0.0342 0.5407 0.6741 0.036 Uiso calc R 1 . . H
    H21 0.4122 0.4637 0.2024 0.053 Uiso calc R 1 . . H
    H22A 0.4628 0.3387 0.0504 0.034 Uiso calc R 1 . . H
    H22B 0.4045 0.4211 0.0083 0.034 Uiso calc R 1 . . H
    H212 0.8438 0.2353 -0.0554 0.033 Uiso calc R 1 . . H
    H213 0.8689 0.1060 -0.1171 0.037 Uiso calc R 1 . . H
    H214 0.7386 0.0593 -0.2228 0.040 Uiso calc R 1 . . H
    H215 0.5825 0.1401 -0.2649 0.041 Uiso calc R 1 . . H
    H216 0.5528 0.2673 -0.1999 0.035 Uiso calc R 1 . . H
    H26 0.7377 0.4560 -0.0313 0.030 Uiso calc R 1 . . H
    H27 0.8513 0.3768 -0.1447 0.029 Uiso calc R 1 . . H
    H222 0.8276 0.5749 -0.0409 0.030 Uiso calc R 1 . . H
    H223 0.9526 0.6849 -0.0343 0.032 Uiso calc R 1 . . H
    H22C 1.2756 0.6479 -0.1124 0.056 Uiso calc R 1 . . H
    H22D 1.2676 0.7480 -0.1234 0.056 Uiso calc R 1 . . H
    H22E 1.2036 0.6873 -0.1906 0.056 Uiso calc R 1 . . H
    H225 1.1552 0.5459 -0.1577 0.031 Uiso calc R 1 . . H
    H226 1.0277 0.4361 -0.1649 0.031 Uiso calc R 1 . . H
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
    C11 O12 . 1.205(2) no
    C11 O11 . 1.3133(19) no
    C11 C12 . 1.493(2) no
    O11 H11 . 0.84 no
    C12 O13 . 1.416(2) no
    C12 H12A . 0.99 no
    C12 H12B . 0.99 no
    O13 N14 . 1.4214(16) no
    N14 C15 . 1.289(2) no
    C15 C16 . 1.452(2) no
    C15 C111 . 1.501(2) no
    C111 C116 . 1.381(2) no
    C111 C112 . 1.386(2) no
    C112 C113 . 1.385(2) no
    C112 H112 . 0.95 no
    C113 C114 . 1.377(3) no
    C113 H113 . 0.95 no
    C114 C115 . 1.370(3) no
    C114 H114 . 0.95 no
    C115 C116 . 1.383(2) no
    C115 H115 . 0.95 no
    C116 H116 . 0.95 no
    C16 C17 . 1.344(2) no
    C16 H16 . 0.95 no
    C17 C121 . 1.455(2) no
    C17 H17 . 0.95 no
    C121 C126 . 1.395(2) no
    C121 C122 . 1.401(2) no
    C122 C123 . 1.369(2) no
    C122 H122 . 0.95 no
    C123 C124 . 1.393(2) no
    C123 H123 . 0.95 no
    C124 O124 . 1.374(2) no
    C124 C125 . 1.382(2) no
    O124 C127 . 1.432(2) no
    C127 H12C . 0.98 no
    C127 H12D . 0.98 no
    C127 H12E . 0.98 no
    C125 C126 . 1.381(2) no
    C125 H125 . 0.95 no
    C126 H126 . 0.95 no
    C21 O22 . 1.217(2) no
    C21 O21 . 1.3184(19) no
    C21 C22 . 1.493(2) no
    O21 H21 . 0.84 no
    C22 O23 . 1.4200(18) no
    C22 H22A . 0.99 no
    C22 H22B . 0.99 no
    O23 N24 . 1.4243(16) no
    N24 C25 . 1.298(2) no
    C25 C26 . 1.448(2) no
    C25 C211 . 1.491(2) no
    C211 C212 . 1.386(2) no
    C211 C216 . 1.392(2) no
    C212 C213 . 1.385(2) no
    C212 H212 . 0.95 no
    C213 C214 . 1.381(2) no
    C213 H213 . 0.95 no
    C214 C215 . 1.376(3) no
    C214 H214 . 0.95 no
    C215 C216 . 1.391(2) no
    C215 H215 . 0.95 no
    C216 H216 . 0.95 no
    C26 C27 . 1.339(2) no
    C26 H26 . 0.95 no
    C27 C221 . 1.459(2) no
    C27 H27 . 0.95 no
    C221 C226 . 1.394(2) no
    C221 C222 . 1.406(2) no
    C222 C223 . 1.368(2) no
    C222 H222 . 0.95 no
    C223 C224 . 1.394(2) no
    C223 H223 . 0.95 no
    C224 O224 . 1.3655(19) no
    C224 C225 . 1.389(2) no
    O224 C227 . 1.428(2) no
    C227 H22C . 0.98 no
    C227 H22D . 0.98 no
    C227 H22E . 0.98 no
    C225 C226 . 1.383(2) no
    C225 H225 . 0.95 no
    C226 H226 . 0.95 no
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
    O12 C11 O11 . . 124.25(15) no
    O12 C11 C12 . . 123.92(15) no
    O11 C11 C12 . . 111.82(15) no
    C11 O11 H11 . . 109.5 no
    O13 C12 C11 . . 108.81(14) no
    O13 C12 H12A . . 109.9 no
    C11 C12 H12A . . 109.9 no
    O13 C12 H12B . . 109.9 no
    C11 C12 H12B . . 109.9 no
    H12A C12 H12B . . 108.3 no
    C12 O13 N14 . . 107.10(12) no
    C15 N14 O13 . . 110.93(13) no
    N14 C15 C16 . . 127.14(15) no
    N14 C15 C111 . . 113.24(14) no
    C16 C15 C111 . . 119.62(14) no
    C116 C111 C112 . . 119.06(16) no
    C116 C111 C15 . . 120.45(15) no
    C112 C111 C15 . . 120.49(15) no
    C113 C112 C111 . . 120.44(18) no
    C113 C112 H112 . . 119.8 no
    C111 C112 H112 . . 119.8 no
    C114 C113 C112 . . 119.91(19) no
    C114 C113 H113 . . 120.0 no
    C112 C113 H113 . . 120.0 no
    C115 C114 C113 . . 119.89(17) no
    C115 C114 H114 . . 120.1 no
    C113 C114 H114 . . 120.1 no
    C114 C115 C116 . . 120.47(17) no
    C114 C115 H115 . . 119.8 no
    C116 C115 H115 . . 119.8 no
    C111 C116 C115 . . 120.23(17) no
    C111 C116 H116 . . 119.9 no
    C115 C116 H116 . . 119.9 no
    C17 C16 C15 . . 122.28(15) no
    C17 C16 H16 . . 118.9 no
    C15 C16 H16 . . 118.9 no
    C16 C17 C121 . . 128.17(15) no
    C16 C17 H17 . . 115.9 no
    C121 C17 H17 . . 115.9 no
    C126 C121 C122 . . 117.33(15) no
    C126 C121 C17 . . 118.72(15) no
    C122 C121 C17 . . 123.95(15) no
    C123 C122 C121 . . 120.99(15) no
    C123 C122 H122 . . 119.5 no
    C121 C122 H122 . . 119.5 no
    C122 C123 C124 . . 120.48(15) no
    C122 C123 H123 . . 119.8 no
    C124 C123 H123 . . 119.8 no
    O124 C124 C125 . . 124.30(15) no
    O124 C124 C123 . . 115.78(14) no
    C125 C124 C123 . . 119.90(15) no
    C124 O124 C127 . . 118.23(13) no
    O124 C127 H12C . . 109.5 no
    O124 C127 H12D . . 109.5 no
    H12C C127 H12D . . 109.5 no
    O124 C127 H12E . . 109.5 no
    H12C C127 H12E . . 109.5 no
    H12D C127 H12E . . 109.5 no
    C126 C125 C124 . . 119.02(15) no
    C126 C125 H125 . . 120.5 no
    C124 C125 H125 . . 120.5 no
    C125 C126 C121 . . 122.27(15) no
    C125 C126 H126 . . 118.9 no
    C121 C126 H126 . . 118.9 no
    O22 C21 O21 . . 124.63(15) no
    O22 C21 C22 . . 124.88(15) no
    O21 C21 C22 . . 110.49(14) no
    C21 O21 H21 . . 109.5 no
    O23 C22 C21 . . 109.27(13) no
    O23 C22 H22A . . 109.8 no
    C21 C22 H22A . . 109.8 no
    O23 C22 H22B . . 109.8 no
    C21 C22 H22B . . 109.8 no
    H22A C22 H22B . . 108.3 no
    C22 O23 N24 . . 107.72(11) no
    C25 N24 O23 . . 111.00(12) no
    N24 C25 C26 . . 124.97(14) no
    N24 C25 C211 . . 112.42(13) no
    C26 C25 C211 . . 122.60(14) no
    C212 C211 C216 . . 119.30(15) no
    C212 C211 C25 . . 120.66(14) no
    C216 C211 C25 . . 119.89(15) no
    C213 C212 C211 . . 120.70(16) no
    C213 C212 H212 . . 119.6 no
    C211 C212 H212 . . 119.6 no
    C214 C213 C212 . . 119.75(16) no
    C214 C213 H213 . . 120.1 no
    C212 C213 H213 . . 120.1 no
    C215 C214 C213 . . 120.09(15) no
    C215 C214 H214 . . 120.0 no
    C213 C214 H214 . . 120.0 no
    C214 C215 C216 . . 120.47(16) no
    C214 C215 H215 . . 119.8 no
    C216 C215 H215 . . 119.8 no
    C215 C216 C211 . . 119.67(16) no
    C215 C216 H216 . . 120.2 no
    C211 C216 H216 . . 120.2 no
    C27 C26 C25 . . 124.86(14) no
    C27 C26 H26 . . 117.6 no
    C25 C26 H26 . . 117.6 no
    C26 C27 C221 . . 125.93(15) no
    C26 C27 H27 . . 117.0 no
    C221 C27 H27 . . 117.0 no
    C226 C221 C222 . . 117.13(14) no
    C226 C221 C27 . . 119.58(14) no
    C222 C221 C27 . . 123.28(14) no
    C223 C222 C221 . . 121.43(15) no
    C223 C222 H222 . . 119.3 no
    C221 C222 H222 . . 119.3 no
    C222 C223 C224 . . 120.11(15) no
    C222 C223 H223 . . 119.9 no
    C224 C223 H223 . . 119.9 no
    O224 C224 C225 . . 124.52(14) no
    O224 C224 C223 . . 115.39(14) no
    C225 C224 C223 . . 120.09(15) no
    C224 O224 C227 . . 117.71(13) no
    O224 C227 H22C . . 109.5 no
    O224 C227 H22D . . 109.5 no
    H22C C227 H22D . . 109.5 no
    O224 C227 H22E . . 109.5 no
    H22C C227 H22E . . 109.5 no
    H22D C227 H22E . . 109.5 no
    C226 C225 C224 . . 118.89(15) no
    C226 C225 H225 . . 120.6 no
    C224 C225 H225 . . 120.6 no
    C225 C226 C221 . . 122.34(15) no
    C225 C226 H226 . . 118.8 no
    C221 C226 H226 . . 118.8 no
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
    O12 C11 C12 O13 . . . . 7.0(2) no
    O11 C11 C12 O13 . . . . -173.35(14) no
    C11 C12 O13 N14 . . . . -158.92(13) no
    C12 O13 N14 C15 . . . . -177.91(14) no
    O13 N14 C15 C16 . . . . 1.1(2) no
    O13 N14 C15 C111 . . . . -179.28(12) no
    N14 C15 C111 C116 . . . . -73.7(2) no
    C16 C15 C111 C116 . . . . 105.94(19) no
    N14 C15 C111 C112 . . . . 107.38(19) no
    C16 C15 C111 C112 . . . . -73.0(2) no
    C116 C111 C112 C113 . . . . 0.5(3) no
    C15 C111 C112 C113 . . . . 179.39(17) no
    C111 C112 C113 C114 . . . . -0.6(3) no
    C112 C113 C114 C115 . . . . -0.1(3) no
    C113 C114 C115 C116 . . . . 1.1(3) no
    C112 C111 C116 C115 . . . . 0.5(3) no
    C15 C111 C116 C115 . . . . -178.47(16) no
    C114 C115 C116 C111 . . . . -1.2(3) no
    N14 C15 C16 C17 . . . . 172.97(16) no
    C111 C15 C16 C17 . . . . -6.6(2) no
    C15 C16 C17 C121 . . . . -178.62(15) no
    C16 C17 C121 C126 . . . . -171.99(17) no
    C16 C17 C121 C122 . . . . 8.3(3) no
    C126 C121 C122 C123 . . . . -0.5(2) no
    C17 C121 C122 C123 . . . . 179.22(15) no
    C121 C122 C123 C124 . . . . 0.4(3) no
    C122 C123 C124 O124 . . . . -178.29(14) no
    C122 C123 C124 C125 . . . . 0.3(2) no
    C125 C124 O124 C127 . . . . -0.3(2) no
    C123 C124 O124 C127 . . . . 178.30(14) no
    O124 C124 C125 C126 . . . . 177.48(15) no
    C123 C124 C125 C126 . . . . -1.0(2) no
    C124 C125 C126 C121 . . . . 1.0(3) no
    C122 C121 C126 C125 . . . . -0.3(2) no
    C17 C121 C126 C125 . . . . -179.95(15) no
    O22 C21 C22 O23 . . . . -3.9(2) no
    O21 C21 C22 O23 . . . . 176.70(13) no
    C21 C22 O23 N24 . . . . 145.91(13) no
    C22 O23 N24 C25 . . . . -172.06(13) no
    O23 N24 C25 C26 . . . . -0.3(2) no
    O23 N24 C25 C211 . . . . 178.15(12) no
    N24 C25 C211 C212 . . . . -119.08(16) no
    C26 C25 C211 C212 . . . . 59.4(2) no
    N24 C25 C211 C216 . . . . 56.44(19) no
    C26 C25 C211 C216 . . . . -125.06(17) no
    C216 C211 C212 C213 . . . . -1.0(2) no
    C25 C211 C212 C213 . . . . 174.59(14) no
    C211 C212 C213 C214 . . . . 1.5(2) no
    C212 C213 C214 C215 . . . . -0.6(3) no
    C213 C214 C215 C216 . . . . -0.8(3) no
    C214 C215 C216 C211 . . . . 1.3(2) no
    C212 C211 C216 C215 . . . . -0.4(2) no
    C25 C211 C216 C215 . . . . -175.98(14) no
    N24 C25 C26 C27 . . . . -170.89(15) no
    C211 C25 C26 C27 . . . . 10.8(2) no
    C25 C26 C27 C221 . . . . 178.06(15) no
    C26 C27 C221 C226 . . . . 168.28(15) no
    C26 C27 C221 C222 . . . . -11.1(3) no
    C226 C221 C222 C223 . . . . 0.2(2) no
    C27 C221 C222 C223 . . . . 179.62(15) no
    C221 C222 C223 C224 . . . . 0.3(2) no
    C222 C223 C224 O224 . . . . 178.72(14) no
    C222 C223 C224 C225 . . . . -1.1(2) no
    C225 C224 O224 C227 . . . . 5.8(2) no
    C223 C224 O224 C227 . . . . -173.96(13) no
    O224 C224 C225 C226 . . . . -178.40(14) no
    C223 C224 C225 C226 . . . . 1.4(2) no
    C224 C225 C226 C221 . . . . -0.9(2) no
    C222 C221 C226 C225 . . . . 0.1(2) no
    C27 C221 C226 C225 . . . . -179.32(15) no
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
    O11 H11 O22 . 0.84 1.81 2.6542(17) 177 y
    O21 H21 O12 . 0.84 1.80 2.6410(17) 178 y
    C215 H215 Cg2 2_644 0.95 2.64 3.532(2) 157 y
