##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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 2.1.    #
#                                                                            #
# 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                                                              #
#                                                                            #
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data_global
_audit_creation_method     'manual editing of form.cif'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2005-06-23
_journal_date_accepted     2005-08-16
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2005
_journal_volume     61
_journal_issue     10
_journal_page_first     o593
_journal_page_last     o595
_journal_paper_category     FO
_journal_coeditor_code     FG1861
_publ_contact_author_name     'Zhi Min Jin'
_publ_contact_author_address
;
College of Pharmaceutical Science
Zhejiang University of Technology
Hangzhou 310014
People's Republic of China
;
_publ_contact_author_email     zhimin-J@163.net
_publ_contact_author_fax     '86-571-87951264'
_publ_contact_author_phone     '86-571-85984972'
_publ_section_title
;
Hydrogen bonding and π--π interactions in a laminar structure:
benzene-1,3-dicarboxylic acid--4-methylpyridine (1/2)
;
loop_
    _publ_author_name
    _publ_author_address
    'Zhi-Min Jin'
;
College of Pharmaceutical Sciences
Zhejiang University of Technology
Hangzhou 310014
People's Republic of China
;
    'Hai Feng'
;
Department of Chemistry
Zhejiang University
Hangzhou 310027
People's Republic of China
;
    'Li Li'
;
College of Pharmaceutical Sciences
Zhejiang University of Technology
Hangzhou 310014
People's Republic of China
;
    'Mao-Lin Hu'
;
Department of Chemistry
Wenzhou Normal College
Wenzhou
Zhejiang 325003
People's Republic of China
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
Benzene-1,3-dicarboxylic acid--4-methylpyridine (1/2)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H6 O4 , 2C6 H7 N'
_chemical_formula_sum     'C20 H20 N2 O4'
_chemical_formula_iupac     'C8 H6 O4 , 2C6 H7 N'
_chemical_formula_weight     352.38
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'C c'
_symmetry_space_group_name_Hall     'C -2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x, -y, z+1/2'
    'x+1/2, y+1/2, z'
    'x+1/2, -y+1/2, z+1/2'
_cell_length_a     6.863(6)
_cell_length_b     39.81(3)
_cell_length_c     13.527(11)
_cell_angle_alpha     90.00
_cell_angle_beta     93.276(15)
_cell_angle_gamma     90.00
_cell_volume     3690(5)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     239
_cell_measurement_theta_min     2.78
_cell_measurement_theta_max     24.94
_cell_measurement_temperature     273(2)
_exptl_crystal_description     sheet
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.269
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1488.0
_exptl_absorpt_coefficient_mu     0.089
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS, Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.974
_exptl_absorpt_correction_T_max     0.982
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     273(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     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9779
_diffrn_reflns_av_R_equivalents     0.0205
_diffrn_reflns_av_sigmaI/netI     0.0232
_diffrn_reflns_theta_min     1.82
_diffrn_reflns_theta_max     25.37
_diffrn_reflns_theta_full     25.37
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -48
_diffrn_reflns_limit_k_max     22
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(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     3370
_reflns_number_gt     2692
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0787
_refine_ls_R_factor_gt     0.0652
_refine_ls_wR_factor_gt     0.1617
_refine_ls_wR_factor_ref     0.1733
_refine_ls_goodness_of_fit_ref     1.068
_refine_ls_restrained_S_all     1.067
_refine_ls_number_reflns     3370
_refine_ls_number_parameters     476
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0929P)²+1.2415P] 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     0.173
_refine_diff_density_min     -0.302
_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 0.0000
                         '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 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 2000)'
_computing_structure_solution     'SHELXTL (Bruker, 2000)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'SHELXTL'
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 0.2147(6) 0.33835(9) 0.0019(4) 0.1012(14) Uani d . 1 . . O
    O2 0.4830(5) 0.36691(8) -0.0152(3) 0.0812(10) Uani d . 1 . . O
    H2O 0.5275 0.3482 -0.0251 0.122 Uiso calc R 1 . . H
    O3 0.2247(7) 0.51441(9) 0.0713(4) 0.1042(14) Uani d . 1 . . O
    O4 0.4901(6) 0.48775(8) 0.0365(3) 0.0899(11) Uani d . 1 . . O
    H4O 0.5363 0.5067 0.0416 0.135 Uiso calc R 1 . . H
    C1 0.3002(6) 0.42725(10) 0.0228(3) 0.0519(10) Uani d . 1 . . C
    H1 0.4319 0.4279 0.0100 0.062 Uiso calc R 1 . . H
    C2 0.2020(6) 0.39680(11) 0.0198(3) 0.0551(10) Uani d . 1 . . C
    C3 0.0045(7) 0.39670(14) 0.0367(4) 0.0713(13) Uani d . 1 . . C
    H3 -0.0636 0.3765 0.0351 0.086 Uiso calc R 1 . . H
    C4 -0.0911(8) 0.42577(15) 0.0556(4) 0.0784(15) Uani d . 1 . . C
    H4 -0.2239 0.4254 0.0659 0.094 Uiso calc R 1 . . H
    C5 0.0076(8) 0.45523(13) 0.0593(4) 0.0716(14) Uani d . 1 . . C
    H5 -0.0585 0.4750 0.0721 0.086 Uiso calc R 1 . . H
    C6 0.2048(7) 0.45638(12) 0.0443(3) 0.0590(11) Uani d . 1 . . C
    C7 0.3056(9) 0.48884(13) 0.0515(4) 0.0731(14) Uani d . 1 . . C
    C8 0.2998(7) 0.36443(13) 0.0007(4) 0.0672(13) Uani d . 1 . . C
    O5 0.3772(7) 0.66089(9) 0.1996(4) 0.1077(15) Uani d . 1 . . O
    O6 0.1199(6) 0.68873(9) 0.2399(3) 0.0911(13) Uani d . 1 . . O
    H6O 0.0748 0.6697 0.2439 0.137 Uiso calc R 1 . . H
    O7 0.3832(6) 0.83852(10) 0.2210(4) 0.1106(16) Uani d . 1 . . O
    O8 0.1101(5) 0.81067(8) 0.2217(3) 0.0807(10) Uani d . 1 . . O
    H8O 0.0666 0.8296 0.2293 0.121 Uiso calc R 1 . . H
    C9 0.2976(7) 0.74981(10) 0.2137(3) 0.0563(11) Uani d . 1 . . C
    H9 0.1667 0.7497 0.2281 0.068 Uiso calc R 1 . . H
    C10 0.3968(7) 0.72003(12) 0.2036(3) 0.0594(11) Uani d . 1 . . C
    C11 0.5924(7) 0.72041(14) 0.1840(4) 0.0716(14) Uani d . 1 . . C
    H11 0.6597 0.7003 0.1791 0.086 Uiso calc R 1 . . H
    C12 0.6866(8) 0.74981(14) 0.1718(4) 0.0778(15) Uani d . 1 . . C
    H12 0.8174 0.7497 0.1572 0.093 Uiso calc R 1 . . H
    C13 0.5903(7) 0.77967(14) 0.1807(4) 0.0711(14) Uani d . 1 . . C
    H13 0.6555 0.7999 0.1725 0.085 Uiso calc R 1 . . H
    C14 0.3947(7) 0.77966(12) 0.2022(3) 0.0592(11) Uani d . 1 . . C
    C15 0.2970(7) 0.81222(13) 0.2159(4) 0.0689(13) Uani d . 1 . . C
    C16 0.2970(8) 0.68695(13) 0.2134(4) 0.0709(13) Uani d . 1 . . C
    N1 0.6286(7) 0.30605(10) -0.0410(3) 0.0731(11) Uani d . 1 . . N
    C17 0.5080(8) 0.28102(14) -0.0314(4) 0.0767(14) Uani d . 1 . . C
    H17 0.3792 0.2855 -0.0180 0.092 Uiso calc R 1 . . H
    C18 0.5683(10) 0.24759(14) -0.0407(5) 0.0828(18) Uani d . 1 . . C
    H18 0.4802 0.2301 -0.0339 0.099 Uiso calc R 1 . . H
    C19 0.7606(9) 0.24083(13) -0.0603(4) 0.0707(14) Uani d . 1 . . C
    C20 0.8765(8) 0.26817(14) -0.0687(4) 0.0739(13) Uani d . 1 . . C
    H20 1.0071 0.2651 -0.0813 0.089 Uiso calc R 1 . . H
    C21 0.8092(8) 0.29907(14) -0.0594(4) 0.0774(14) Uani d . 1 . . C
    H21 0.8953 0.3169 -0.0663 0.093 Uiso calc R 1 . . H
    C22 0.8317(12) 0.20595(15) -0.0709(5) 0.110(2) Uani d . 1 . . C
    H22A 0.8604 0.2020 -0.1385 0.164 Uiso calc R 1 . . H
    H22B 0.7329 0.1905 -0.0521 0.164 Uiso calc R 1 . . H
    H22C 0.9477 0.2028 -0.0289 0.164 Uiso calc R 1 . . H
    N2 0.6291(10) 0.55001(13) 0.0338(4) 0.0918(14) Uani d . 1 . . N
    C23 0.5144(8) 0.57432(17) 0.0448(4) 0.0846(16) Uani d . 1 . . C
    H23 0.3867 0.5697 0.0600 0.102 Uiso calc R 1 . . H
    C24 0.5725(12) 0.6087(2) 0.0348(5) 0.112(3) Uani d . 1 . . C
    H24 0.4865 0.6264 0.0422 0.135 Uiso calc R 1 . . H
    C25 0.7725(9) 0.61386(13) 0.0127(4) 0.0750(14) Uani d . 1 . . C
    C26 0.8768(9) 0.58590(15) 0.0059(5) 0.0856(15) Uani d . 1 . . C
    H26 1.0082 0.5878 -0.0066 0.103 Uiso calc R 1 . . H
    C27 0.8035(10) 0.55586(17) 0.0161(5) 0.0976(18) Uani d . 1 . . C
    H27 0.8861 0.5376 0.0097 0.117 Uiso calc R 1 . . H
    C28 0.8604(16) 0.64784(17) -0.0010(6) 0.143(4) Uani d . 1 . . C
    H28A 1.0001 0.6462 0.0056 0.214 Uiso calc R 1 . . H
    H28B 0.8162 0.6629 0.0484 0.214 Uiso calc R 1 . . H
    H28C 0.8215 0.6562 -0.0656 0.214 Uiso calc R 1 . . H
    N3 -0.0249(7) 0.62792(11) 0.2657(3) 0.0777(12) Uani d . 1 . . N
    C29 0.0890(9) 0.60250(16) 0.2555(5) 0.0857(16) Uani d . 1 . . C
    H29 0.2174 0.6064 0.2403 0.103 Uiso calc R 1 . . H
    C30 0.0269(11) 0.56907(16) 0.2665(5) 0.0931(19) Uani d . 1 . . C
    H30 0.1119 0.5512 0.2596 0.112 Uiso calc R 1 . . H
    C31 -0.1649(9) 0.56391(13) 0.2881(4) 0.0784(15) Uani d . 1 . . C
    C32 -0.2749(10) 0.59173(16) 0.2988(5) 0.0855(16) Uani d . 1 . . C
    C33 -0.2040(9) 0.62238(15) 0.2874(5) 0.0866(16) Uani d . 1 . . C
    H33 -0.2859 0.6407 0.2953 0.104 Uiso calc R 1 . . H
    C34 -0.2474(13) 0.5293(2) 0.3007(7) 0.125(3) Uani d . 1 . . C
    H34A -0.3774 0.5310 0.3229 0.188 Uiso calc R 1 . . H
    H34B -0.1669 0.5171 0.3487 0.188 Uiso calc R 1 . . H
    H34C -0.2506 0.5176 0.2385 0.188 Uiso calc R 1 . . H
    N4 -0.0301(7) 0.87121(11) 0.2544(3) 0.0757(12) Uani d . 1 . . N
    C35 0.0856(7) 0.89657(15) 0.2559(4) 0.0749(14) Uani d . 1 . . C
    H35 0.2160 0.8927 0.2441 0.090 Uiso calc R 1 . . H
    C36 0.0285(10) 0.92941(15) 0.2739(4) 0.0861(18) Uani d . 1 . . C
    H36 0.1173 0.9471 0.2741 0.103 Uiso calc R 1 . . H
    C37 -0.1700(9) 0.93494(13) 0.2918(3) 0.0740(15) Uani d . 1 . . C
    C38 -0.2830(8) 0.90716(14) 0.2877(4) 0.0735(13) Uani d . 1 . . C
    H38 -0.4155 0.9091 0.2978 0.088 Uiso calc R 1 . . H
    C39 -0.2087(9) 0.87673(14) 0.2694(4) 0.0812(15) Uani d . 1 . . C
    H39 -0.2934 0.8585 0.2676 0.097 Uiso calc R 1 . . H
    C40 -0.2492(15) 0.96900(16) 0.3115(5) 0.124(3) Uani d . 1 . . C
    H40A -0.2627 0.9814 0.2507 0.186 Uiso calc R 1 . . H
    H40B -0.1614 0.9806 0.3575 0.186 Uiso calc R 1 . . H
    H40C -0.3744 0.9669 0.3391 0.186 Uiso calc R 1 . . H
    H32 -0.404(12) 0.589(2) 0.315(6) 0.148 Uiso d . 1 . . H
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C8 . 1.192(6) yes
    O2 C8 . 1.292(6) yes
    O2 H2O . 0.8200 ?
    O3 C7 . 1.197(6) yes
    O4 C7 . 1.294(7) yes
    O4 H4O . 0.8200 ?
    C1 C6 . 1.372(6) yes
    C1 C2 . 1.387(6) yes
    C1 H1 . 0.9300 ?
    C2 C3 . 1.387(7) yes
    C2 C8 . 1.482(7) yes
    C3 C4 . 1.362(7) yes
    C3 H3 . 0.9300 ?
    C4 C5 . 1.354(7) yes
    C4 H4 . 0.9300 ?
    C5 C6 . 1.381(7) yes
    C5 H5 . 0.9300 ?
    C6 C7 . 1.466(7) yes
    O5 C16 . 1.194(6) ?
    O6 C16 . 1.289(6) ?
    O6 H6O . 0.8200 ?
    O7 C15 . 1.203(6) ?
    O8 C15 . 1.291(6) ?
    O8 H8O . 0.8200 ?
    C9 C14 . 1.376(6) ?
    C9 C10 . 1.378(6) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.383(7) ?
    C10 C16 . 1.494(7) ?
    C11 C12 . 1.352(7) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.369(7) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.390(7) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.476(7) ?
    N1 C17 . 1.306(6) yes
    N1 C21 . 1.308(7) yes
    C17 C18 . 1.402(8) yes
    C17 H17 . 0.9300 ?
    C18 C19 . 1.387(9) yes
    C18 H18 . 0.9300 ?
    C19 C20 . 1.356(8) yes
    C19 C22 . 1.481(8) yes
    C20 C21 . 1.322(8) yes
    C20 H20 . 0.9300 ?
    C21 H21 . 0.9300 ?
    C22 H22A . 0.9600 ?
    C22 H22B . 0.9600 ?
    C22 H22C . 0.9600 ?
    N2 C27 . 1.255(8) ?
    N2 C23 . 1.262(8) ?
    C23 C24 . 1.433(10) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.436(10) ?
    C24 H24 . 0.9300 ?
    C25 C26 . 1.330(8) ?
    C25 C28 . 1.497(8) ?
    C26 C27 . 1.308(8) ?
    C26 H26 . 0.9300 ?
    C27 H27 . 0.9300 ?
    C28 H28A . 0.9600 ?
    C28 H28B . 0.9600 ?
    C28 H28C . 0.9600 ?
    N3 C29 . 1.291(7) ?
    N3 C33 . 1.299(8) ?
    C29 C30 . 1.408(9) ?
    C29 H29 . 0.9300 ?
    C30 C31 . 1.380(9) ?
    C30 H30 . 0.9300 ?
    C31 C32 . 1.353(8) ?
    C31 C34 . 1.504(9) ?
    C32 C33 . 1.326(8) ?
    C32 H32 . 0.93(8) ?
    C33 H33 . 0.9300 ?
    C34 H34A . 0.9600 ?
    C34 H34B . 0.9600 ?
    C34 H34C . 0.9600 ?
    N4 C39 . 1.273(7) ?
    N4 C35 . 1.284(7) ?
    C35 C36 . 1.390(8) ?
    C35 H35 . 0.9300 ?
    C36 C37 . 1.415(9) ?
    C36 H36 . 0.9300 ?
    C37 C38 . 1.350(8) ?
    C37 C40 . 1.490(8) ?
    C38 C39 . 1.343(8) ?
    C38 H38 . 0.9300 ?
    C39 H39 . 0.9300 ?
    C40 H40A . 0.9600 ?
    C40 H40B . 0.9600 ?
    C40 H40C . 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
    C8 O2 H2O . . 109.5 ?
    C7 O4 H4O . . 109.5 ?
    C6 C1 C2 . . 120.5(4) ?
    C6 C1 H1 . . 119.7 ?
    C2 C1 H1 . . 119.7 ?
    C1 C2 C3 . . 118.4(4) ?
    C1 C2 C8 . . 122.7(4) ?
    C3 C2 C8 . . 118.9(4) ?
    C4 C3 C2 . . 120.9(5) ?
    C4 C3 H3 . . 119.5 ?
    C2 C3 H3 . . 119.5 ?
    C5 C4 C3 . . 119.9(5) ?
    C5 C4 H4 . . 120.1 ?
    C3 C4 H4 . . 120.1 ?
    C4 C5 C6 . . 121.1(5) ?
    C4 C5 H5 . . 119.5 ?
    C6 C5 H5 . . 119.5 ?
    C1 C6 C5 . . 119.2(5) ?
    C1 C6 C7 . . 122.0(4) ?
    C5 C6 C7 . . 118.8(5) ?
    O3 C7 O4 . . 122.3(5) ?
    O3 C7 C6 . . 122.8(5) ?
    O4 C7 C6 . . 115.0(5) ?
    O1 C8 O2 . . 123.4(5) ?
    O1 C8 C2 . . 121.9(5) ?
    O2 C8 C2 . . 114.7(4) ?
    C16 O6 H6O . . 109.5 ?
    C15 O8 H8O . . 109.5 ?
    C14 C9 C10 . . 119.1(4) ?
    C14 C9 H9 . . 120.4 ?
    C10 C9 H9 . . 120.4 ?
    C9 C10 C11 . . 120.0(5) ?
    C9 C10 C16 . . 121.2(4) ?
    C11 C10 C16 . . 118.8(5) ?
    C12 C11 C10 . . 120.6(5) ?
    C12 C11 H11 . . 119.7 ?
    C10 C11 H11 . . 119.7 ?
    C11 C12 C13 . . 120.3(5) ?
    C11 C12 H12 . . 119.8 ?
    C13 C12 H12 . . 119.8 ?
    C12 C13 C14 . . 119.7(5) ?
    C12 C13 H13 . . 120.2 ?
    C14 C13 H13 . . 120.2 ?
    C9 C14 C13 . . 120.3(5) ?
    C9 C14 C15 . . 121.2(4) ?
    C13 C14 C15 . . 118.5(4) ?
    O7 C15 O8 . . 121.7(5) ?
    O7 C15 C14 . . 123.1(5) ?
    O8 C15 C14 . . 115.2(4) ?
    O5 C16 O6 . . 122.8(5) ?
    O5 C16 C10 . . 122.3(5) ?
    O6 C16 C10 . . 114.9(4) ?
    C17 N1 C21 . . 118.0(5) ?
    N1 C17 C18 . . 121.6(5) ?
    N1 C17 H17 . . 119.2 ?
    C18 C17 H17 . . 119.2 ?
    C19 C18 C17 . . 119.4(5) ?
    C19 C18 H18 . . 120.3 ?
    C17 C18 H18 . . 120.3 ?
    C20 C19 C18 . . 115.4(5) ?
    C20 C19 C22 . . 123.1(6) ?
    C18 C19 C22 . . 121.5(6) ?
    C21 C20 C19 . . 122.0(5) ?
    C21 C20 H20 . . 119.0 ?
    C19 C20 H20 . . 119.0 ?
    N1 C21 C20 . . 123.7(5) ?
    N1 C21 H21 . . 118.1 ?
    C20 C21 H21 . . 118.1 ?
    C19 C22 H22A . . 109.5 ?
    C19 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C19 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C27 N2 C23 . . 119.2(6) ?
    N2 C23 C24 . . 122.8(6) ?
    N2 C23 H23 . . 118.6 ?
    C24 C23 H23 . . 118.6 ?
    C23 C24 C25 . . 115.5(5) ?
    C23 C24 H24 . . 122.2 ?
    C25 C24 H24 . . 122.2 ?
    C26 C25 C24 . . 114.8(5) ?
    C26 C25 C28 . . 121.7(7) ?
    C24 C25 C28 . . 123.5(7) ?
    C27 C26 C25 . . 123.1(6) ?
    C27 C26 H26 . . 118.4 ?
    C25 C26 H26 . . 118.4 ?
    N2 C27 C26 . . 124.5(7) ?
    N2 C27 H27 . . 117.7 ?
    C26 C27 H27 . . 117.7 ?
    C25 C28 H28A . . 109.5 ?
    C25 C28 H28B . . 109.5 ?
    H28A C28 H28B . . 109.5 ?
    C25 C28 H28C . . 109.5 ?
    H28A C28 H28C . . 109.5 ?
    H28B C28 H28C . . 109.5 ?
    C29 N3 C33 . . 118.5(5) ?
    N3 C29 C30 . . 122.8(5) ?
    N3 C29 H29 . . 118.6 ?
    C30 C29 H29 . . 118.6 ?
    C31 C30 C29 . . 117.5(5) ?
    C31 C30 H30 . . 121.3 ?
    C29 C30 H30 . . 121.3 ?
    C32 C31 C30 . . 116.4(5) ?
    C32 C31 C34 . . 121.5(6) ?
    C30 C31 C34 . . 122.0(6) ?
    C33 C32 C31 . . 122.0(6) ?
    C33 C32 H32 . . 119(5) ?
    C31 C32 H32 . . 119(5) ?
    N3 C33 C32 . . 122.7(6) ?
    N3 C33 H33 . . 118.6 ?
    C32 C33 H33 . . 118.6 ?
    C31 C34 H34A . . 109.5 ?
    C31 C34 H34B . . 109.5 ?
    H34A C34 H34B . . 109.5 ?
    C31 C34 H34C . . 109.5 ?
    H34A C34 H34C . . 109.5 ?
    H34B C34 H34C . . 109.5 ?
    C39 N4 C35 . . 117.5(5) ?
    N4 C35 C36 . . 124.2(5) ?
    N4 C35 H35 . . 117.9 ?
    C36 C35 H35 . . 117.9 ?
    C35 C36 C37 . . 117.4(5) ?
    C35 C36 H36 . . 121.3 ?
    C37 C36 H36 . . 121.3 ?
    C38 C37 C36 . . 115.0(5) ?
    C38 C37 C40 . . 122.6(6) ?
    C36 C37 C40 . . 122.4(6) ?
    C39 C38 C37 . . 121.6(5) ?
    C39 C38 H38 . . 119.2 ?
    C37 C38 H38 . . 119.2 ?
    N4 C39 C38 . . 124.4(5) ?
    N4 C39 H39 . . 117.8 ?
    C38 C39 H39 . . 117.8 ?
    C37 C40 H40A . . 109.5 ?
    C37 C40 H40B . . 109.5 ?
    H40A C40 H40B . . 109.5 ?
    C37 C40 H40C . . 109.5 ?
    H40A C40 H40C . . 109.5 ?
    H40B C40 H40C . . 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
    C6 C1 C2 C3 . . . . 1.6(6) ?
    C6 C1 C2 C8 . . . . -177.6(4) ?
    C1 C2 C3 C4 . . . . 0.1(7) ?
    C8 C2 C3 C4 . . . . 179.3(5) ?
    C2 C3 C4 C5 . . . . -0.9(8) ?
    C3 C4 C5 C6 . . . . -0.1(8) ?
    C2 C1 C6 C5 . . . . -2.5(6) ?
    C2 C1 C6 C7 . . . . 177.8(4) ?
    C4 C5 C6 C1 . . . . 1.8(7) ?
    C4 C5 C6 C7 . . . . -178.5(5) ?
    C1 C6 C7 O3 . . . . -179.2(5) ?
    C5 C6 C7 O3 . . . . 1.1(7) ?
    C1 C6 C7 O4 . . . . -0.3(6) ?
    C5 C6 C7 O4 . . . . 180.0(4) ?
    C1 C2 C8 O1 . . . . 177.3(5) ?
    C3 C2 C8 O1 . . . . -1.9(8) ?
    C1 C2 C8 O2 . . . . -1.5(7) ?
    C3 C2 C8 O2 . . . . 179.3(4) ?
    C14 C9 C10 C11 . . . . 1.2(7) ?
    C14 C9 C10 C16 . . . . -178.8(4) ?
    C9 C10 C11 C12 . . . . -1.9(7) ?
    C16 C10 C11 C12 . . . . 178.1(5) ?
    C10 C11 C12 C13 . . . . 1.4(8) ?
    C11 C12 C13 C14 . . . . -0.2(8) ?
    C10 C9 C14 C13 . . . . -0.1(7) ?
    C10 C9 C14 C15 . . . . -177.7(4) ?
    C12 C13 C14 C9 . . . . -0.4(7) ?
    C12 C13 C14 C15 . . . . 177.3(5) ?
    C9 C14 C15 O7 . . . . 168.6(5) ?
    C13 C14 C15 O7 . . . . -9.1(8) ?
    C9 C14 C15 O8 . . . . -11.6(7) ?
    C13 C14 C15 O8 . . . . 170.7(4) ?
    C9 C10 C16 O5 . . . . 175.8(5) ?
    C11 C10 C16 O5 . . . . -4.1(8) ?
    C9 C10 C16 O6 . . . . -5.7(7) ?
    C11 C10 C16 O6 . . . . 174.3(4) ?
    C21 N1 C17 C18 . . . . -0.3(8) ?
    N1 C17 C18 C19 . . . . 0.2(9) ?
    C17 C18 C19 C20 . . . . 0.1(8) ?
    C17 C18 C19 C22 . . . . 180.0(5) ?
    C18 C19 C20 C21 . . . . -0.5(8) ?
    C22 C19 C20 C21 . . . . 179.7(5) ?
    C17 N1 C21 C20 . . . . 0.0(8) ?
    C19 C20 C21 N1 . . . . 0.4(9) ?
    C27 N2 C23 C24 . . . . 2.1(9) ?
    N2 C23 C24 C25 . . . . -0.9(9) ?
    C23 C24 C25 C26 . . . . -0.9(8) ?
    C23 C24 C25 C28 . . . . 179.7(6) ?
    C24 C25 C26 C27 . . . . 1.6(9) ?
    C28 C25 C26 C27 . . . . -179.0(7) ?
    C23 N2 C27 C26 . . . . -1.5(11) ?
    C25 C26 C27 N2 . . . . -0.5(11) ?
    C33 N3 C29 C30 . . . . 0.3(9) ?
    N3 C29 C30 C31 . . . . 0.7(9) ?
    C29 C30 C31 C32 . . . . -1.4(8) ?
    C29 C30 C31 C34 . . . . 179.6(6) ?
    C30 C31 C32 C33 . . . . 1.2(9) ?
    C34 C31 C32 C33 . . . . -179.7(6) ?
    C29 N3 C33 C32 . . . . -0.5(9) ?
    C31 C32 C33 N3 . . . . -0.3(10) ?
    C39 N4 C35 C36 . . . . 0.8(8) ?
    N4 C35 C36 C37 . . . . 0.2(8) ?
    C35 C36 C37 C38 . . . . -1.0(7) ?
    C35 C36 C37 C40 . . . . -179.7(5) ?
    C36 C37 C38 C39 . . . . 1.1(7) ?
    C40 C37 C38 C39 . . . . 179.7(5) ?
    C35 N4 C39 C38 . . . . -0.8(9) ?
    C37 C38 C39 N4 . . . . -0.2(9) ?
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 H2O N1 . 0.82 1.83 2.652(6) 177 yes
    O4 H4O N2 . 0.82 1.84 2.657(6) 172 yes
    O6 H6O N3 . 0.82 1.83 2.648(6) 175 yes
    O8 H8O N4 . 0.82 1.82 2.642(6) 176 yes
    C17 H17 O1 . 0.93 2.41 3.093(7) 130 yes
    C21 H21 O1 1_655 0.93 2.48 3.258(7) 141 yes
    C23 H23 O3 . 0.93 2.48 3.139(8) 128 yes
    C27 H27 O3 1_655 0.93 2.59 3.375(9) 142 yes
    C29 H29 O5 . 0.93 2.50 3.171(8) 129 yes
    C35 H35 O7 . 0.93 2.47 3.138(7) 129 yes
    C39 H39 O7 1_455 0.93 2.41 3.221(8) 146 yes
